data_jrs167 loop_ _publ_author_name _publ_author_address 'Cohen, Seth M.' ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; 'Thoi, Van S.' ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; 'Stork, Jay R.' ; Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; _publ_contact_author ; Cohen, Seth M. Department of Chemistry and Biochemistry University of California, San Diego La Jolla CA 92093-0358 USA ; _publ_contact_author_email scohen@ucsd.edu _journal_name_full 'Inorganic Chemistry' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common HDADP^Ph,iPr^ _chemical_melting_point ? _chemical_formula_moiety 'C23 H26 N4 O2' _chemical_formula_sum 'C23 H26 N4 O2' _chemical_formula_weight 390.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.7923(19) _cell_length_b 13.3540(17) _cell_length_c 21.442(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.781(2) _cell_angle_gamma 90.00 _cell_volume 4329.4(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3756 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.7 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex' _diffrn_measurement_method \w\f _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39697 _diffrn_reflns_av_R_equivalents 0.1413 _diffrn_reflns_av_sigmaI/netI 0.1592 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7917 _reflns_number_gt 4103 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Apex2 v.1.0-2.1 (Bruker, 2006)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT v7.34A (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All H atoms were located in a difference map. The positions of amide and pyrrole H atoms were allowed to refine freely. All other H atoms were placed in calculated positions and refined with a riding model. The crystal was weakly diffracting, resulting in Rint value greater than 0.1. The asymmetric unit includes two independent molecules, giving a z of 8. Each residue includes one isopropyl group that is disordered over a general position. The major orientations refined to 70(3) % and 77.6(12) %, respectively. Atoms C17 and C17A of one disordered group were set to have equal anisotropic displacement parameters to compensate for excessive correlation. Atoms C24A and C25A in the minor orientation of the other disordered group were isor. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7917 _refine_ls_number_parameters 583 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1806 _refine_ls_R_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0634(3) 0.3765(4) -0.0183(2) 0.0421(13) Uani 1 1 d . . . H1A H 0.0339 0.4401 -0.0338 0.063 Uiso 1 1 calc R . . H1B H 0.0210 0.3214 -0.0316 0.063 Uiso 1 1 calc R . . H1C H 0.1125 0.3665 -0.0371 0.063 Uiso 1 1 calc R . . C2 C 0.1410(3) 0.2803(3) 0.0821(2) 0.0477(14) Uani 1 1 d . . . H2A H 0.1927 0.2682 0.0666 0.071 Uiso 1 1 calc R . . H2B H 0.0982 0.2259 0.0674 0.071 Uiso 1 1 calc R . . H2C H 0.1595 0.2830 0.1298 0.071 Uiso 1 1 calc R . . C3 C 0.0988(3) 0.3786(3) 0.0551(2) 0.0284(11) Uani 1 1 d . . . H3 H 0.0478 0.3907 0.0730 0.034 Uiso 1 1 calc R . . C4 C 0.1743(3) 0.5052(3) 0.1340(2) 0.0195(10) Uani 1 1 d . . . C5 C 0.2447(2) 0.5821(3) 0.15047(19) 0.0160(9) Uani 1 1 d . . . C6 C 0.2950(2) 0.6296(3) 0.1156(2) 0.0192(9) Uani 1 1 d . . . H6 H 0.2890 0.6217 0.0705 0.023 Uiso 1 1 calc R . . C7 C 0.3553(2) 0.6905(3) 0.15879(19) 0.0203(10) Uani 1 1 d . . . H7 H 0.3979 0.7324 0.1483 0.024 Uiso 1 1 calc R . . C8 C 0.3430(3) 0.6798(3) 0.2205(2) 0.0196(9) Uani 1 1 d . . . C9 C 0.3912(2) 0.7236(3) 0.2807(2) 0.0191(10) Uani 1 1 d . . . C10 C 0.3663(3) 0.7181(3) 0.3372(2) 0.0206(10) Uani 1 1 d . . . C11 C 0.4146(3) 0.7553(3) 0.4014(2) 0.0286(11) Uani 1 1 d . . . H11 H 0.4683 0.7922 0.4122 0.034 Uiso 1 1 calc R . . C12 C 0.3690(3) 0.7277(3) 0.4427(2) 0.0305(11) Uani 1 1 d . . . H12 H 0.3834 0.7412 0.4881 0.037 Uiso 1 1 calc R . . C13 C 0.2940(3) 0.6735(3) 0.4038(2) 0.0246(10) Uani 1 1 d . . . C14 C 0.2266(3) 0.6264(3) 0.4311(2) 0.0329(12) Uani 1 1 d . A . C15 C 0.0859(6) 0.5421(6) 0.4137(4) 0.032(2) Uani 0.776(12) 1 d PD A 1 H15 H 0.0794 0.5831 0.4511 0.039 Uiso 0.776(12) 1 calc PR A 1 C16 C 0.0016(4) 0.5439(5) 0.3586(4) 0.033(2) Uani 0.776(12) 1 d PD A 1 H16A H -0.0128 0.6131 0.3443 0.049 Uiso 0.776(12) 1 calc PR A 1 H16B H -0.0466 0.5155 0.3733 0.049 Uiso 0.776(12) 1 calc PR A 1 H16C H 0.0092 0.5041 0.3221 0.049 Uiso 0.776(12) 1 calc PR A 1 C17 C 0.1087(7) 0.4327(11) 0.4352(8) 0.061(3) Uani 0.776(12) 1 d PD A 1 H17A H 0.1207 0.3951 0.3994 0.092 Uiso 0.776(12) 1 calc PR A 1 H17B H 0.0588 0.4021 0.4466 0.092 Uiso 0.776(12) 1 calc PR A 1 H17C H 0.1612 0.4314 0.4731 0.092 Uiso 0.776(12) 1 calc PR A 1 C15A C 0.085(2) 0.495(3) 0.3894(18) 0.063(12) Uani 0.224(12) 1 d PD A 2 H15A H 0.0623 0.4578 0.3475 0.076 Uiso 0.224(12) 1 calc PR A 2 C16A C 0.0164(18) 0.5601(18) 0.4071(15) 0.057(9) Uani 0.224(12) 1 d PD A 2 H16D H -0.0307 0.5176 0.4141 0.085 Uiso 0.224(12) 1 calc PR A 2 H16E H -0.0090 0.6072 0.3716 0.085 Uiso 0.224(12) 1 calc PR A 2 H16F H 0.0446 0.5974 0.4471 0.085 Uiso 0.224(12) 1 calc PR A 2 C17A C 0.132(3) 0.430(4) 0.449(3) 0.061(3) Uani 0.224(12) 1 d PD A 2 H17D H 0.1570 0.4731 0.4864 0.092 Uiso 0.224(12) 1 calc PR A 2 H17E H 0.1798 0.3922 0.4386 0.092 Uiso 0.224(12) 1 calc PR A 2 H17F H 0.0897 0.3834 0.4583 0.092 Uiso 0.224(12) 1 calc PR A 2 C18 C 0.4765(3) 0.7731(3) 0.28184(19) 0.0217(10) Uani 1 1 d . . . C19 C 0.4940(3) 0.8723(3) 0.2997(2) 0.0318(11) Uani 1 1 d . . . H19 H 0.4507 0.9114 0.3115 0.038 Uiso 1 1 calc R . . C20 C 0.5744(3) 0.9148(4) 0.3005(2) 0.0438(14) Uani 1 1 d . . . H20 H 0.5855 0.9834 0.3115 0.053 Uiso 1 1 calc R . . C21 C 0.6385(3) 0.8571(3) 0.2853(2) 0.0368(12) Uani 1 1 d . . . H21 H 0.6941 0.8857 0.2868 0.044 Uiso 1 1 calc R . . C22 C 0.6215(3) 0.7584(3) 0.2679(2) 0.0282(11) Uani 1 1 d . . . H22 H 0.6657 0.7188 0.2578 0.034 Uiso 1 1 calc R . . C23 C 0.5407(2) 0.7166(3) 0.26521(19) 0.0235(10) Uani 1 1 d . . . H23 H 0.5288 0.6489 0.2519 0.028 Uiso 1 1 calc R . . C24 C 0.3917(5) 1.0633(10) 0.0349(5) 0.060(4) Uani 0.77(2) 1 d P B 1 H24A H 0.3766 1.0075 0.0040 0.090 Uiso 0.77(2) 1 calc PR B 1 H24B H 0.4440 1.0981 0.0299 0.090 Uiso 0.77(2) 1 calc PR B 1 H24C H 0.3419 1.1101 0.0264 0.090 Uiso 0.77(2) 1 calc PR B 1 C25 C 0.4911(6) 0.9552(7) 0.1187(7) 0.057(3) Uani 0.77(2) 1 d P B 1 H25A H 0.5000 0.9240 0.1615 0.085 Uiso 0.77(2) 1 calc PR B 1 H25B H 0.5435 0.9945 0.1187 0.085 Uiso 0.77(2) 1 calc PR B 1 H25C H 0.4814 0.9031 0.0852 0.085 Uiso 0.77(2) 1 calc PR B 1 C26 C 0.4115(3) 1.0231(3) 0.1043(2) 0.0323(11) Uani 0.77(2) 1 d P B 1 H26 H 0.4240 1.0804 0.1357 0.039 Uiso 0.77(2) 1 calc PR B 1 C24A C 0.3807(17) 1.111(2) 0.0638(17) 0.049(9) Uiso 0.23(2) 1 d P B 2 H24D H 0.3393 1.0900 0.0223 0.074 Uiso 0.23(2) 1 calc PR B 2 H24E H 0.4313 1.1451 0.0555 0.074 Uiso 0.23(2) 1 calc PR B 2 H24F H 0.3508 1.1567 0.0862 0.074 Uiso 0.23(2) 1 calc PR B 2 C25A C 0.479(3) 0.957(3) 0.088(2) 0.071(14) Uiso 0.23(2) 1 d P B 2 H25D H 0.4930 0.9003 0.1181 0.106 Uiso 0.23(2) 1 calc PR B 2 H25E H 0.5328 0.9952 0.0907 0.106 Uiso 0.23(2) 1 calc PR B 2 H25F H 0.4548 0.9313 0.0431 0.106 Uiso 0.23(2) 1 calc PR B 2 C26A C 0.4115(3) 1.0231(3) 0.1043(2) 0.0323(11) Uani 0.23(2) 1 d P B 2 H26A H 0.4415 1.0500 0.1488 0.039 Uiso 0.23(2) 1 calc PR B 2 C27 C 0.3099(3) 0.9677(3) 0.1659(2) 0.0257(10) Uani 1 1 d . B . C28 C 0.2324(2) 0.9051(3) 0.16438(19) 0.0177(9) Uani 1 1 d . . . C29 C 0.1715(3) 0.8508(3) 0.1166(2) 0.0230(10) Uani 1 1 d . . . H29 H 0.1707 0.8440 0.0723 0.028 Uiso 1 1 calc R . . C30 C 0.1121(2) 0.8082(3) 0.14558(19) 0.0211(10) Uani 1 1 d . . . H30 H 0.0628 0.7677 0.1244 0.025 Uiso 1 1 calc R . . C31 C 0.1375(2) 0.8353(3) 0.2116(2) 0.0181(9) Uani 1 1 d . . . C32 C 0.0980(3) 0.8143(3) 0.2620(2) 0.0204(10) Uani 1 1 d . . . C33 C 0.1312(2) 0.8487(3) 0.3250(2) 0.0189(10) Uani 1 1 d . . . C34 C 0.0984(3) 0.8290(3) 0.3803(2) 0.0217(10) Uani 1 1 d . . . H34 H 0.0488 0.7888 0.3804 0.026 Uiso 1 1 calc R . . C35 C 0.1518(2) 0.8788(3) 0.4319(2) 0.0205(10) Uani 1 1 d . . . H35 H 0.1474 0.8803 0.4751 0.025 Uiso 1 1 calc R . . C36 C 0.2160(3) 0.9287(3) 0.40762(19) 0.0192(9) Uani 1 1 d . . . C37 C 0.2849(3) 0.9991(3) 0.4454(2) 0.0203(10) Uani 1 1 d . . . C38 C 0.4105(3) 1.1059(3) 0.4414(2) 0.0302(11) Uani 1 1 d . . . H38 H 0.4328 1.0980 0.4897 0.036 Uiso 1 1 calc R . . C39 C 0.3701(3) 1.2086(3) 0.4262(3) 0.0505(15) Uani 1 1 d . . . H39A H 0.3518 1.2190 0.3789 0.076 Uiso 1 1 calc R . . H39B H 0.4138 1.2594 0.4471 0.076 Uiso 1 1 calc R . . H39C H 0.3185 1.2140 0.4427 0.076 Uiso 1 1 calc R . . C40 C 0.4874(3) 1.0915(4) 0.4129(2) 0.0439(14) Uani 1 1 d . . . H40A H 0.5136 1.0252 0.4251 0.066 Uiso 1 1 calc R . . H40B H 0.5321 1.1432 0.4300 0.066 Uiso 1 1 calc R . . H40C H 0.4660 1.0968 0.3654 0.066 Uiso 1 1 calc R . . C41 C 0.0150(3) 0.7556(3) 0.2434(2) 0.0217(10) Uani 1 1 d . . . C42 C 0.0116(3) 0.6621(3) 0.2139(2) 0.0244(10) Uani 1 1 d . . . H42 H 0.0633 0.6349 0.2063 0.029 Uiso 1 1 calc R . . C43 C -0.0667(3) 0.6090(3) 0.1958(2) 0.0355(12) Uani 1 1 d . . . H43 H -0.0682 0.5444 0.1769 0.043 Uiso 1 1 calc R . . C44 C -0.1429(3) 0.6493(3) 0.2049(2) 0.0359(12) Uani 1 1 d . . . H44 H -0.1970 0.6132 0.1914 0.043 Uiso 1 1 calc R . . C45 C -0.1403(3) 0.7425(3) 0.2337(2) 0.0366(13) Uani 1 1 d . . . H45 H -0.1925 0.7700 0.2403 0.044 Uiso 1 1 calc R . . C46 C -0.0617(3) 0.7957(3) 0.2528(2) 0.0263(10) Uani 1 1 d . . . H46 H -0.0602 0.8598 0.2725 0.032 Uiso 1 1 calc R . . N1 N 0.1611(2) 0.4615(2) 0.07571(17) 0.0233(9) Uani 1 1 d . . . H1 H 0.201(2) 0.468(3) 0.0535(19) 0.028 Uiso 1 1 d . . . N2 N 0.2739(2) 0.6138(2) 0.21293(16) 0.0177(8) Uani 1 1 d . . . H2 H 0.253(2) 0.599(3) 0.2470(18) 0.021 Uiso 1 1 d . . . N3 N 0.2903(2) 0.6668(2) 0.34170(16) 0.0197(8) Uani 1 1 d . . . N4 N 0.1587(3) 0.5824(3) 0.3895(2) 0.0390(11) Uani 1 1 d . . . H4 H 0.155(3) 0.576(3) 0.349(2) 0.047 Uiso 1 1 d . . . N5 N 0.3350(2) 0.9670(3) 0.11130(18) 0.0289(9) Uani 1 1 d . . . H5 H 0.304(3) 0.934(3) 0.075(2) 0.035 Uiso 1 1 d . . . N6 N 0.2112(2) 0.8942(2) 0.22080(17) 0.0200(8) Uani 1 1 d . . . H6A H 0.236(2) 0.919(3) 0.2591(19) 0.024 Uiso 1 1 d . . . N7 N 0.20631(19) 0.9111(2) 0.34562(16) 0.0174(8) Uani 1 1 d . . . N8 N 0.3443(2) 1.0290(3) 0.41534(16) 0.0217(8) Uani 1 1 d . . . H8 H 0.339(2) 1.006(3) 0.3757(19) 0.026 Uiso 1 1 d . . . O1 O 0.13321(17) 0.4850(2) 0.17310(13) 0.0261(7) Uani 1 1 d . . . O2 O 0.2365(2) 0.6301(3) 0.49056(15) 0.0451(9) Uani 1 1 d . . . O3 O 0.34796(18) 1.0141(2) 0.21552(14) 0.0293(7) Uani 1 1 d . . . O4 O 0.28628(17) 1.0282(2) 0.50021(13) 0.0280(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.045(3) 0.045(3) 0.030(3) -0.012(2) 0.000(3) -0.018(2) C2 0.065(4) 0.029(3) 0.044(3) -0.006(2) 0.008(3) -0.015(3) C3 0.029(3) 0.030(3) 0.031(3) -0.009(2) 0.016(2) -0.013(2) C4 0.020(2) 0.017(2) 0.025(3) 0.0021(18) 0.010(2) 0.0012(18) C5 0.016(2) 0.015(2) 0.018(2) -0.0009(17) 0.0056(19) 0.0056(17) C6 0.022(2) 0.018(2) 0.019(2) -0.0031(18) 0.010(2) 0.0021(18) C7 0.022(2) 0.010(2) 0.033(3) -0.0032(19) 0.014(2) -0.0022(18) C8 0.017(2) 0.011(2) 0.032(3) 0.0004(19) 0.009(2) 0.0037(18) C9 0.018(2) 0.009(2) 0.029(3) -0.0015(18) 0.005(2) -0.0009(17) C10 0.020(2) 0.018(2) 0.023(3) -0.0011(18) 0.004(2) 0.0078(18) C11 0.023(2) 0.026(3) 0.031(3) -0.005(2) -0.001(2) -0.001(2) C12 0.033(3) 0.029(3) 0.027(3) -0.001(2) 0.003(2) 0.003(2) C13 0.027(3) 0.024(3) 0.026(3) 0.001(2) 0.012(2) 0.011(2) C14 0.031(3) 0.032(3) 0.036(3) 0.007(2) 0.010(3) 0.014(2) C15 0.039(5) 0.032(5) 0.027(4) 0.010(3) 0.010(4) 0.000(4) C16 0.039(4) 0.031(4) 0.028(4) 0.006(3) 0.009(4) -0.008(3) C17 0.027(7) 0.076(5) 0.064(9) 0.052(5) -0.012(6) -0.013(5) C15A 0.05(2) 0.06(3) 0.10(3) 0.01(2) 0.05(2) 0.010(19) C16A 0.045(18) 0.053(18) 0.05(2) 0.024(15) -0.013(17) 0.020(14) C17A 0.027(7) 0.076(5) 0.064(9) 0.052(5) -0.012(6) -0.013(5) C18 0.021(2) 0.018(2) 0.023(3) 0.0023(19) 0.002(2) 0.0025(19) C19 0.023(2) 0.024(3) 0.049(3) -0.002(2) 0.011(2) 0.005(2) C20 0.031(3) 0.026(3) 0.076(4) -0.008(3) 0.016(3) -0.005(2) C21 0.028(3) 0.023(3) 0.059(4) -0.003(2) 0.012(3) -0.005(2) C22 0.022(2) 0.028(3) 0.037(3) -0.004(2) 0.013(2) 0.003(2) C23 0.020(2) 0.019(2) 0.030(3) -0.0041(19) 0.006(2) -0.0039(19) C24 0.047(5) 0.070(7) 0.067(7) 0.029(5) 0.021(4) -0.030(4) C25 0.027(5) 0.070(6) 0.082(9) 0.024(6) 0.029(6) -0.008(4) C26 0.032(3) 0.029(3) 0.040(3) -0.007(2) 0.017(2) -0.012(2) C26A 0.032(3) 0.029(3) 0.040(3) -0.007(2) 0.017(2) -0.012(2) C27 0.025(3) 0.025(3) 0.028(3) 0.003(2) 0.010(2) 0.003(2) C28 0.016(2) 0.012(2) 0.026(3) -0.0007(18) 0.008(2) 0.0024(17) C29 0.028(2) 0.019(2) 0.025(3) -0.0025(19) 0.013(2) 0.0000(19) C30 0.017(2) 0.021(2) 0.026(3) -0.0045(19) 0.006(2) 0.0012(18) C31 0.016(2) 0.011(2) 0.027(3) -0.0051(18) 0.006(2) -0.0031(17) C32 0.020(2) 0.013(2) 0.028(3) -0.0015(19) 0.008(2) 0.0022(18) C33 0.015(2) 0.011(2) 0.034(3) -0.0018(18) 0.011(2) 0.0022(17) C34 0.019(2) 0.015(2) 0.035(3) -0.0005(19) 0.013(2) -0.0025(18) C35 0.020(2) 0.023(2) 0.021(3) 0.0031(19) 0.010(2) -0.0019(19) C36 0.023(2) 0.014(2) 0.022(3) 0.0023(18) 0.010(2) 0.0037(18) C37 0.019(2) 0.019(2) 0.024(3) 0.0031(19) 0.009(2) -0.0005(18) C38 0.029(3) 0.039(3) 0.027(3) -0.011(2) 0.015(2) -0.017(2) C39 0.056(4) 0.034(3) 0.068(4) -0.020(3) 0.028(3) -0.018(3) C40 0.033(3) 0.053(4) 0.049(3) -0.013(3) 0.018(3) -0.023(2) C41 0.020(2) 0.015(2) 0.032(3) -0.0016(19) 0.011(2) -0.0013(18) C42 0.021(2) 0.019(2) 0.036(3) -0.004(2) 0.013(2) -0.0040(19) C43 0.034(3) 0.028(3) 0.049(3) -0.011(2) 0.019(3) -0.007(2) C44 0.025(3) 0.030(3) 0.055(4) -0.013(2) 0.016(3) -0.016(2) C45 0.021(2) 0.039(3) 0.055(4) -0.014(2) 0.018(2) -0.006(2) C46 0.021(2) 0.026(3) 0.030(3) -0.009(2) 0.006(2) -0.003(2) N1 0.023(2) 0.025(2) 0.026(2) -0.0071(17) 0.0133(17) -0.0060(17) N2 0.0193(19) 0.0170(19) 0.020(2) 0.0005(15) 0.0104(17) -0.0011(15) N3 0.0192(19) 0.016(2) 0.025(2) 0.0033(15) 0.0085(17) 0.0038(15) N4 0.034(2) 0.048(3) 0.040(3) 0.014(2) 0.019(2) -0.004(2) N5 0.030(2) 0.032(2) 0.030(2) -0.0090(18) 0.017(2) -0.0127(17) N6 0.021(2) 0.019(2) 0.021(2) -0.0060(16) 0.0072(18) -0.0015(16) N7 0.0134(18) 0.0142(19) 0.025(2) -0.0008(15) 0.0070(16) -0.0013(14) N8 0.027(2) 0.022(2) 0.019(2) -0.0077(16) 0.0115(18) -0.0115(16) O1 0.0277(17) 0.0247(17) 0.0310(19) -0.0053(13) 0.0166(15) -0.0058(13) O2 0.051(2) 0.062(2) 0.029(2) 0.0125(17) 0.0206(18) 0.0190(18) O3 0.0342(19) 0.0297(19) 0.0238(18) -0.0005(14) 0.0082(15) -0.0086(14) O4 0.0279(17) 0.0361(19) 0.0222(18) -0.0053(14) 0.0109(15) -0.0093(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.511(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.510(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N1 1.463(5) . ? C3 H3 1.0000 . ? C4 O1 1.229(4) . ? C4 N1 1.340(5) . ? C4 C5 1.479(5) . ? C5 N2 1.352(5) . ? C5 C6 1.390(5) . ? C6 C7 1.384(5) . ? C6 H6 0.9500 . ? C7 C8 1.398(5) . ? C7 H7 0.9500 . ? C8 N2 1.376(5) . ? C8 C9 1.422(5) . ? C9 C10 1.380(5) . ? C9 C18 1.493(5) . ? C10 N3 1.409(5) . ? C10 C11 1.455(5) . ? C11 C12 1.345(5) . ? C11 H11 0.9500 . ? C12 C13 1.433(6) . ? C12 H12 0.9500 . ? C13 N3 1.319(5) . ? C13 C14 1.494(6) . ? C14 O2 1.239(5) . ? C14 N4 1.320(6) . ? C15 N4 1.492(9) . ? C15 C16 1.504(8) . ? C15 C17 1.543(12) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C15A C16A 1.514(18) . ? C15A C17A 1.54(2) . ? C15A N4 1.65(4) . ? C15A H15A 1.0000 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 0.9800 . ? C17A H17D 0.9800 . ? C17A H17E 0.9800 . ? C17A H17F 0.9800 . ? C18 C19 1.384(5) . ? C18 C23 1.390(5) . ? C19 C20 1.387(6) . ? C19 H19 0.9500 . ? C20 C21 1.383(6) . ? C20 H20 0.9500 . ? C21 C22 1.375(6) . ? C21 H21 0.9500 . ? C22 C23 1.380(5) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C26 1.527(9) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.508(9) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N5 1.466(5) . ? C26 H26 1.0000 . ? C24A H24D 0.9800 . ? C24A H24E 0.9800 . ? C24A H24F 0.9800 . ? C25A H25D 0.9800 . ? C25A H25E 0.9800 . ? C25A H25F 0.9800 . ? C27 O3 1.227(5) . ? C27 N5 1.341(5) . ? C27 C28 1.474(5) . ? C28 N6 1.353(5) . ? C28 C29 1.390(5) . ? C29 C30 1.388(5) . ? C29 H29 0.9500 . ? C30 C31 1.402(5) . ? C30 H30 0.9500 . ? C31 N6 1.370(5) . ? C31 C32 1.424(5) . ? C32 C33 1.378(5) . ? C32 C41 1.480(5) . ? C33 N7 1.413(5) . ? C33 C34 1.447(5) . ? C34 C35 1.356(5) . ? C34 H34 0.9500 . ? C35 C36 1.431(5) . ? C35 H35 0.9500 . ? C36 N7 1.315(5) . ? C36 C37 1.488(5) . ? C37 O4 1.232(4) . ? C37 N8 1.343(5) . ? C38 N8 1.458(5) . ? C38 C39 1.507(6) . ? C38 C40 1.519(5) . ? C38 H38 1.0000 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C46 1.392(5) . ? C41 C42 1.393(5) . ? C42 C43 1.381(5) . ? C42 H42 0.9500 . ? C43 C44 1.384(6) . ? C43 H43 0.9500 . ? C44 C45 1.384(6) . ? C44 H44 0.9500 . ? C45 C46 1.386(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N1 H1 0.89(4) . ? N2 H2 0.91(4) . ? N4 H4 0.86(4) . ? N5 H5 0.91(4) . ? N6 H6A 0.86(4) . ? N8 H8 0.88(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C2 110.9(4) . . ? N1 C3 C1 110.1(3) . . ? C2 C3 C1 111.9(4) . . ? N1 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? C1 C3 H3 107.9 . . ? O1 C4 N1 124.8(4) . . ? O1 C4 C5 119.9(4) . . ? N1 C4 C5 115.4(3) . . ? N2 C5 C6 107.8(3) . . ? N2 C5 C4 118.1(3) . . ? C6 C5 C4 134.0(4) . . ? C7 C6 C5 107.3(4) . . ? C7 C6 H6 126.3 . . ? C5 C6 H6 126.3 . . ? C6 C7 C8 108.4(3) . . ? C6 C7 H7 125.8 . . ? C8 C7 H7 125.8 . . ? N2 C8 C7 106.0(4) . . ? N2 C8 C9 124.7(4) . . ? C7 C8 C9 129.3(4) . . ? C10 C9 C8 124.2(4) . . ? C10 C9 C18 119.6(4) . . ? C8 C9 C18 116.1(3) . . ? C9 C10 N3 123.4(4) . . ? C9 C10 C11 127.5(4) . . ? N3 C10 C11 109.0(3) . . ? C12 C11 C10 107.2(4) . . ? C12 C11 H11 126.4 . . ? C10 C11 H11 126.4 . . ? C11 C12 C13 105.4(4) . . ? C11 C12 H12 127.3 . . ? C13 C12 H12 127.3 . . ? N3 C13 C12 114.2(4) . . ? N3 C13 C14 122.6(4) . . ? C12 C13 C14 123.1(4) . . ? O2 C14 N4 123.4(5) . . ? O2 C14 C13 119.6(4) . . ? N4 C14 C13 117.0(4) . . ? N4 C15 C16 108.5(6) . . ? N4 C15 C17 107.9(9) . . ? C16 C15 C17 109.1(8) . . ? N4 C15 H15 110.4 . . ? C16 C15 H15 110.4 . . ? C17 C15 H15 110.4 . . ? C16A C15A C17A 109(3) . . ? C16A C15A N4 99(3) . . ? C17A C15A N4 103(3) . . ? C16A C15A H15A 114.8 . . ? C17A C15A H15A 114.8 . . ? N4 C15A H15A 114.8 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15A C17A H17D 109.5 . . ? C15A C17A H17E 108.0 . . ? H17D C17A H17E 109.5 . . ? C15A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C19 C18 C23 119.2(4) . . ? C19 C18 C9 122.3(4) . . ? C23 C18 C9 118.5(4) . . ? C18 C19 C20 120.3(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 119.9(4) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C22 C21 C20 120.0(4) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C18 120.3(4) . . ? C22 C23 H23 119.8 . . ? C18 C23 H23 119.8 . . ? N5 C26 C25 109.6(4) . . ? N5 C26 C24 109.6(4) . . ? C25 C26 C24 109.5(6) . . ? N5 C26 H26 109.4 . . ? C25 C26 H26 109.4 . . ? C24 C26 H26 109.4 . . ? H24D C24A H24E 109.5 . . ? H24D C24A H24F 109.5 . . ? H24E C24A H24F 109.5 . . ? H25D C25A H25E 109.5 . . ? H25D C25A H25F 109.5 . . ? H25E C25A H25F 109.5 . . ? O3 C27 N5 124.5(4) . . ? O3 C27 C28 120.1(4) . . ? N5 C27 C28 115.4(4) . . ? N6 C28 C29 107.8(3) . . ? N6 C28 C27 117.3(4) . . ? C29 C28 C27 134.9(4) . . ? C30 C29 C28 107.3(4) . . ? C30 C29 H29 126.4 . . ? C28 C29 H29 126.4 . . ? C29 C30 C31 108.2(4) . . ? C29 C30 H30 125.9 . . ? C31 C30 H30 125.9 . . ? N6 C31 C30 106.1(3) . . ? N6 C31 C32 122.9(4) . . ? C30 C31 C32 131.0(4) . . ? C33 C32 C31 123.6(4) . . ? C33 C32 C41 119.8(4) . . ? C31 C32 C41 116.6(4) . . ? C32 C33 N7 123.3(3) . . ? C32 C33 C34 128.1(4) . . ? N7 C33 C34 108.5(3) . . ? C35 C34 C33 107.1(3) . . ? C35 C34 H34 126.5 . . ? C33 C34 H34 126.5 . . ? C34 C35 C36 105.7(3) . . ? C34 C35 H35 127.1 . . ? C36 C35 H35 127.1 . . ? N7 C36 C35 113.4(4) . . ? N7 C36 C37 121.1(3) . . ? C35 C36 C37 125.5(4) . . ? O4 C37 N8 122.8(4) . . ? O4 C37 C36 121.8(4) . . ? N8 C37 C36 115.4(4) . . ? N8 C38 C39 110.3(4) . . ? N8 C38 C40 109.0(3) . . ? C39 C38 C40 111.5(4) . . ? N8 C38 H38 108.7 . . ? C39 C38 H38 108.7 . . ? C40 C38 H38 108.7 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C40 H40A 109.5 . . ? C38 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C38 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C46 C41 C42 119.3(4) . . ? C46 C41 C32 119.8(4) . . ? C42 C41 C32 120.8(3) . . ? C43 C42 C41 120.2(4) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C42 C43 C44 120.3(4) . . ? C42 C43 H43 119.8 . . ? C44 C43 H43 119.8 . . ? C43 C44 C45 119.8(4) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C44 C45 C46 120.2(4) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C41 120.1(4) . . ? C45 C46 H46 119.9 . . ? C41 C46 H46 119.9 . . ? C4 N1 C3 121.4(3) . . ? C4 N1 H1 121(3) . . ? C3 N1 H1 115(3) . . ? C5 N2 C8 110.4(3) . . ? C5 N2 H2 129(2) . . ? C8 N2 H2 121(2) . . ? C13 N3 C10 104.2(3) . . ? C14 N4 C15 118.9(4) . . ? C14 N4 C15A 138.8(13) . . ? C14 N4 H4 123(3) . . ? C15 N4 H4 119(3) . . ? C15A N4 H4 95(3) . . ? C27 N5 C26 123.1(4) . . ? C27 N5 H5 123(3) . . ? C26 N5 H5 114(3) . . ? C28 N6 C31 110.6(3) . . ? C28 N6 H6A 131(3) . . ? C31 N6 H6A 119(3) . . ? C36 N7 C33 105.3(3) . . ? C37 N8 C38 123.3(3) . . ? C37 N8 H8 118(3) . . ? C38 N8 H8 118(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C4 C5 N2 12.8(6) . . . . ? N1 C4 C5 N2 -166.5(3) . . . . ? O1 C4 C5 C6 -171.2(4) . . . . ? N1 C4 C5 C6 9.5(7) . . . . ? N2 C5 C6 C7 0.2(4) . . . . ? C4 C5 C6 C7 -176.0(4) . . . . ? C5 C6 C7 C8 0.6(5) . . . . ? C6 C7 C8 N2 -1.2(4) . . . . ? C6 C7 C8 C9 177.1(4) . . . . ? N2 C8 C9 C10 -10.7(6) . . . . ? C7 C8 C9 C10 171.3(4) . . . . ? N2 C8 C9 C18 165.8(3) . . . . ? C7 C8 C9 C18 -12.2(6) . . . . ? C8 C9 C10 N3 0.9(6) . . . . ? C18 C9 C10 N3 -175.4(3) . . . . ? C8 C9 C10 C11 175.9(4) . . . . ? C18 C9 C10 C11 -0.4(6) . . . . ? C9 C10 C11 C12 -175.8(4) . . . . ? N3 C10 C11 C12 -0.2(5) . . . . ? C10 C11 C12 C13 0.4(5) . . . . ? C11 C12 C13 N3 -0.4(5) . . . . ? C11 C12 C13 C14 178.2(4) . . . . ? N3 C13 C14 O2 175.6(4) . . . . ? C12 C13 C14 O2 -2.9(6) . . . . ? N3 C13 C14 N4 -4.4(6) . . . . ? C12 C13 C14 N4 177.2(4) . . . . ? C10 C9 C18 C19 -59.7(6) . . . . ? C8 C9 C18 C19 123.7(4) . . . . ? C10 C9 C18 C23 119.4(4) . . . . ? C8 C9 C18 C23 -57.2(5) . . . . ? C23 C18 C19 C20 0.5(7) . . . . ? C9 C18 C19 C20 179.5(4) . . . . ? C18 C19 C20 C21 -2.0(7) . . . . ? C19 C20 C21 C22 1.5(8) . . . . ? C20 C21 C22 C23 0.4(7) . . . . ? C21 C22 C23 C18 -1.9(7) . . . . ? C19 C18 C23 C22 1.5(6) . . . . ? C9 C18 C23 C22 -177.6(4) . . . . ? O3 C27 C28 N6 -5.9(6) . . . . ? N5 C27 C28 N6 172.4(4) . . . . ? O3 C27 C28 C29 174.0(4) . . . . ? N5 C27 C28 C29 -7.7(7) . . . . ? N6 C28 C29 C30 1.0(5) . . . . ? C27 C28 C29 C30 -178.9(4) . . . . ? C28 C29 C30 C31 -0.9(5) . . . . ? C29 C30 C31 N6 0.4(4) . . . . ? C29 C30 C31 C32 177.9(4) . . . . ? N6 C31 C32 C33 -1.8(6) . . . . ? C30 C31 C32 C33 -178.8(4) . . . . ? N6 C31 C32 C41 175.8(4) . . . . ? C30 C31 C32 C41 -1.3(6) . . . . ? C31 C32 C33 N7 2.2(6) . . . . ? C41 C32 C33 N7 -175.3(3) . . . . ? C31 C32 C33 C34 -177.6(4) . . . . ? C41 C32 C33 C34 4.9(6) . . . . ? C32 C33 C34 C35 -179.7(4) . . . . ? N7 C33 C34 C35 0.5(4) . . . . ? C33 C34 C35 C36 0.4(4) . . . . ? C34 C35 C36 N7 -1.2(5) . . . . ? C34 C35 C36 C37 175.2(4) . . . . ? N7 C36 C37 O4 168.8(4) . . . . ? C35 C36 C37 O4 -7.4(6) . . . . ? N7 C36 C37 N8 -10.7(6) . . . . ? C35 C36 C37 N8 173.1(4) . . . . ? C33 C32 C41 C46 56.4(6) . . . . ? C31 C32 C41 C46 -121.2(4) . . . . ? C33 C32 C41 C42 -126.4(4) . . . . ? C31 C32 C41 C42 56.0(5) . . . . ? C46 C41 C42 C43 -1.6(6) . . . . ? C32 C41 C42 C43 -178.8(4) . . . . ? C41 C42 C43 C44 2.0(7) . . . . ? C42 C43 C44 C45 -1.4(7) . . . . ? C43 C44 C45 C46 0.6(7) . . . . ? C44 C45 C46 C41 -0.2(7) . . . . ? C42 C41 C46 C45 0.8(6) . . . . ? C32 C41 C46 C45 178.0(4) . . . . ? O1 C4 N1 C3 -4.3(6) . . . . ? C5 C4 N1 C3 175.0(4) . . . . ? C2 C3 N1 C4 -83.0(5) . . . . ? C1 C3 N1 C4 152.6(4) . . . . ? C6 C5 N2 C8 -1.0(4) . . . . ? C4 C5 N2 C8 176.0(3) . . . . ? C7 C8 N2 C5 1.3(4) . . . . ? C9 C8 N2 C5 -177.1(4) . . . . ? C12 C13 N3 C10 0.3(5) . . . . ? C14 C13 N3 C10 -178.3(4) . . . . ? C9 C10 N3 C13 175.7(4) . . . . ? C11 C10 N3 C13 0.0(4) . . . . ? O2 C14 N4 C15 5.2(8) . . . . ? C13 C14 N4 C15 -174.8(5) . . . . ? O2 C14 N4 C15A -23.0(16) . . . . ? C13 C14 N4 C15A 157.0(14) . . . . ? C16 C15 N4 C14 152.1(6) . . . . ? C17 C15 N4 C14 -89.8(9) . . . . ? C16 C15 N4 C15A -67(3) . . . . ? C17 C15 N4 C15A 51(3) . . . . ? C16A C15A N4 C14 86(2) . . . . ? C17A C15A N4 C14 -26(3) . . . . ? C16A C15A N4 C15 28.9(14) . . . . ? C17A C15A N4 C15 -83(4) . . . . ? O3 C27 N5 C26 -0.5(7) . . . . ? C28 C27 N5 C26 -178.8(4) . . . . ? C25 C26 N5 C27 96.0(7) . . . . ? C24 C26 N5 C27 -143.8(7) . . . . ? C29 C28 N6 C31 -0.7(5) . . . . ? C27 C28 N6 C31 179.2(3) . . . . ? C30 C31 N6 C28 0.2(4) . . . . ? C32 C31 N6 C28 -177.5(4) . . . . ? C35 C36 N7 C33 1.5(4) . . . . ? C37 C36 N7 C33 -175.1(3) . . . . ? C32 C33 N7 C36 179.0(4) . . . . ? C34 C33 N7 C36 -1.2(4) . . . . ? O4 C37 N8 C38 -6.5(7) . . . . ? C36 C37 N8 C38 173.0(4) . . . . ? C39 C38 N8 C37 -80.6(5) . . . . ? C40 C38 N8 C37 156.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.89(4) 2.01(4) 2.897(4) 175(4) 4_575 N2 H2 N3 0.91(4) 2.15(4) 2.789(5) 127(3) . N5 H5 O2 0.91(4) 2.01(4) 2.912(5) 177(4) 4_575 N6 H6A N7 0.86(4) 2.04(4) 2.709(5) 134(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.255 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.058 #===END data_jrs171 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; H~2~DADP^Ph,iPr^Br^.^H~2~O^.^3CHCl~3~ ; _chemical_melting_point ? _chemical_formula_moiety ; C23 H27 N4 O2, 3(C H Cl3), H2 O, Br ; _chemical_formula_sum 'C26 H32 Br Cl9 N4 O3' _chemical_formula_weight 847.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.987(3) _cell_length_b 20.692(5) _cell_length_c 25.444(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.605(5) _cell_angle_gamma 90.00 _cell_volume 7340(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9713 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.2 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3424 _exptl_absorpt_coefficient_mu 1.809 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5235 _exptl_absorpt_correction_T_max 0.7296 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 93094 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 26.37 _reflns_number_total 14795 _reflns_number_gt 11600 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Apex2 v.1.0-2.1 (Bruker, 2006)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT v7.34A (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All H atoms were located in a difference map, placed in calculated positions, and treated with a riding model. Water H atoms were restrained to approximate conventional geometry. One Cl atom of a chloroform molecule is disordered over two positions. The major orientation had an occupancy of 51(3) percent. The highest electron density peak of 1.26 e/A^3^ is 0.93 A from CL19 of the disordered CHCl3 molecule. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+11.3921P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14795 _refine_ls_number_parameters 805 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.77065(2) 0.218058(15) 0.483463(11) 0.02435(8) Uani 1 1 d . . . Br2 Br 0.53713(2) 0.390799(16) 0.565002(12) 0.03109(8) Uani 1 1 d . . . C1 C 0.8362(2) 0.27686(17) 0.99661(11) 0.0299(7) Uani 1 1 d . . . H1A H 0.8377 0.2305 0.9890 0.045 Uiso 1 1 calc R . . H1B H 0.7806 0.2866 1.0164 0.045 Uiso 1 1 calc R . . H1C H 0.8952 0.2892 1.0176 0.045 Uiso 1 1 calc R . . C2 C 0.8255(3) 0.38684(17) 0.95398(14) 0.0372(8) Uani 1 1 d . . . H2A H 0.8831 0.4004 0.9757 0.056 Uiso 1 1 calc R . . H2B H 0.7684 0.3978 0.9721 0.056 Uiso 1 1 calc R . . H2C H 0.8230 0.4091 0.9199 0.056 Uiso 1 1 calc R . . C3 C 0.8287(2) 0.31460(15) 0.94518(11) 0.0232(6) Uani 1 1 d . . . H3 H 0.7681 0.3015 0.9243 0.028 Uiso 1 1 calc R . . C4 C 0.90456(19) 0.30293(13) 0.86231(10) 0.0178(6) Uani 1 1 d . . . C5 C 0.99360(19) 0.28938(13) 0.83615(10) 0.0172(6) Uani 1 1 d . . . C6 C 1.08805(19) 0.27676(14) 0.85519(11) 0.0203(6) Uani 1 1 d . . . H6 H 1.1108 0.2712 0.8911 0.024 Uiso 1 1 calc R . . C7 C 1.1425(2) 0.27376(14) 0.81211(11) 0.0204(6) Uani 1 1 d . . . H7 H 1.2098 0.2666 0.8132 0.025 Uiso 1 1 calc R . . C8 C 1.08065(19) 0.28314(13) 0.76659(10) 0.0177(6) Uani 1 1 d . . . C9 C 1.09886(19) 0.28204(13) 0.71257(10) 0.0177(6) Uani 1 1 d . . . C10 C 1.02717(19) 0.25998(14) 0.67480(10) 0.0180(6) Uani 1 1 d . . . C11 C 1.0079(2) 0.27548(14) 0.62116(10) 0.0200(6) Uani 1 1 d . . . H11 H 1.0462 0.3020 0.6008 0.024 Uiso 1 1 calc R . . C12 C 0.9236(2) 0.24534(14) 0.60349(10) 0.0208(6) Uani 1 1 d . . . H12 H 0.8926 0.2479 0.5689 0.025 Uiso 1 1 calc R . . C13 C 0.89199(19) 0.21013(13) 0.64608(10) 0.0180(6) Uani 1 1 d . . . C14 C 0.80672(19) 0.16874(13) 0.65157(10) 0.0172(6) Uani 1 1 d . . . C15 C 0.6584(2) 0.12295(15) 0.60945(11) 0.0237(6) Uani 1 1 d . . . H15 H 0.6362 0.1244 0.6458 0.028 Uiso 1 1 calc R . . C16 C 0.5805(2) 0.15206(17) 0.57158(12) 0.0305(7) Uani 1 1 d . . . H16A H 0.5702 0.1973 0.5811 0.046 Uiso 1 1 calc R . . H16B H 0.5207 0.1278 0.5737 0.046 Uiso 1 1 calc R . . H16C H 0.6002 0.1499 0.5355 0.046 Uiso 1 1 calc R . . C17 C 0.6788(3) 0.05343(16) 0.59613(13) 0.0362(8) Uani 1 1 d . . . H17A H 0.7000 0.0510 0.5604 0.054 Uiso 1 1 calc R . . H17B H 0.6204 0.0277 0.5980 0.054 Uiso 1 1 calc R . . H17C H 0.7293 0.0365 0.6213 0.054 Uiso 1 1 calc R . . C18 C 1.1918(2) 0.30413(14) 0.69747(11) 0.0201(6) Uani 1 1 d . . . C19 C 1.2422(2) 0.35172(15) 0.72772(11) 0.0235(6) Uani 1 1 d . . . H19 H 1.2151 0.3696 0.7575 0.028 Uiso 1 1 calc R . . C20 C 1.3311(2) 0.37271(15) 0.71440(12) 0.0284(7) Uani 1 1 d . . . H20 H 1.3655 0.4041 0.7356 0.034 Uiso 1 1 calc R . . C21 C 1.3699(2) 0.34808(16) 0.67025(13) 0.0316(7) Uani 1 1 d . . . H21 H 1.4301 0.3634 0.6607 0.038 Uiso 1 1 calc R . . C22 C 1.3212(2) 0.30108(16) 0.63987(13) 0.0297(7) Uani 1 1 d . . . H22 H 1.3485 0.2840 0.6098 0.036 Uiso 1 1 calc R . . C23 C 1.2329(2) 0.27886(15) 0.65312(11) 0.0240(6) Uani 1 1 d . . . H23 H 1.2000 0.2465 0.6323 0.029 Uiso 1 1 calc R . . C24 C 0.8060(2) 0.48695(15) 0.61412(12) 0.0318(7) Uani 1 1 d . . . H24A H 0.7415 0.4966 0.5982 0.048 Uiso 1 1 calc R . . H24B H 0.8528 0.5145 0.5982 0.048 Uiso 1 1 calc R . . H24C H 0.8087 0.4951 0.6521 0.048 Uiso 1 1 calc R . . C25 C 0.8246(2) 0.40066(16) 0.54604(12) 0.0305(7) Uani 1 1 d . . . H25A H 0.8358 0.3543 0.5414 0.046 Uiso 1 1 calc R . . H25B H 0.8737 0.4254 0.5294 0.046 Uiso 1 1 calc R . . H25C H 0.7611 0.4121 0.5296 0.046 Uiso 1 1 calc R . . C26 C 0.8295(2) 0.41643(14) 0.60452(11) 0.0232(6) Uani 1 1 d . . . H26 H 0.8960 0.4075 0.6202 0.028 Uiso 1 1 calc R . . C27 C 0.78319(19) 0.34695(13) 0.67701(10) 0.0170(6) Uani 1 1 d . . . C28 C 0.70792(19) 0.30507(13) 0.69632(10) 0.0176(6) Uani 1 1 d . . . C29 C 0.6162(2) 0.28773(14) 0.67550(11) 0.0210(6) Uani 1 1 d . . . H29 H 0.5874 0.2990 0.6417 0.025 Uiso 1 1 calc R . . C30 C 0.5748(2) 0.25114(14) 0.71306(11) 0.0219(6) Uani 1 1 d . . . H30 H 0.5116 0.2339 0.7102 0.026 Uiso 1 1 calc R . . C31 C 0.64299(19) 0.24405(13) 0.75616(10) 0.0176(6) Uani 1 1 d . . . C32 C 0.63905(19) 0.20867(13) 0.80318(10) 0.0176(6) Uani 1 1 d . . . C33 C 0.72139(19) 0.18039(13) 0.82823(10) 0.0172(6) Uani 1 1 d . . . C34 C 0.7425(2) 0.16469(14) 0.88209(10) 0.0201(6) Uani 1 1 d . . . H34 H 0.6994 0.1678 0.9090 0.024 Uiso 1 1 calc R . . C35 C 0.8359(2) 0.14413(14) 0.88857(11) 0.0208(6) Uani 1 1 d . . . H35 H 0.8696 0.1312 0.9208 0.025 Uiso 1 1 calc R . . C36 C 0.87289(19) 0.14572(13) 0.83852(10) 0.0173(6) Uani 1 1 d . . . C37 C 0.96994(19) 0.13100(13) 0.82145(11) 0.0187(6) Uani 1 1 d . . . C38 C 1.13244(19) 0.09451(14) 0.85096(12) 0.0232(6) Uani 1 1 d . . . H38 H 1.1570 0.1308 0.8299 0.028 Uiso 1 1 calc R . . C39 C 1.1868(2) 0.09409(16) 0.90505(13) 0.0318(7) Uani 1 1 d . . . H39A H 1.1791 0.1360 0.9222 0.048 Uiso 1 1 calc R . . H39B H 1.2550 0.0862 0.9013 0.048 Uiso 1 1 calc R . . H39C H 1.1614 0.0598 0.9266 0.048 Uiso 1 1 calc R . . C40 C 1.1452(2) 0.03150(16) 0.82169(13) 0.0323(7) Uani 1 1 d . . . H40A H 1.1249 -0.0047 0.8430 0.049 Uiso 1 1 calc R . . H40B H 1.2129 0.0261 0.8152 0.049 Uiso 1 1 calc R . . H40C H 1.1062 0.0324 0.7880 0.049 Uiso 1 1 calc R . . C41 C 0.54851(19) 0.20412(14) 0.82788(10) 0.0194(6) Uani 1 1 d . . . C42 C 0.4881(2) 0.25837(15) 0.82757(11) 0.0239(6) Uani 1 1 d . . . H42 H 0.5036 0.2963 0.8090 0.029 Uiso 1 1 calc R . . C43 C 0.4058(2) 0.25634(16) 0.85438(12) 0.0279(7) Uani 1 1 d . . . H43 H 0.3663 0.2936 0.8553 0.033 Uiso 1 1 calc R . . C44 C 0.3809(2) 0.20026(17) 0.87985(12) 0.0309(7) Uani 1 1 d . . . H44 H 0.3240 0.1990 0.8979 0.037 Uiso 1 1 calc R . . C45 C 0.4391(2) 0.14606(16) 0.87897(12) 0.0288(7) Uani 1 1 d . . . H45 H 0.4214 0.1075 0.8960 0.035 Uiso 1 1 calc R . . C46 C 0.5225(2) 0.14781(15) 0.85358(11) 0.0230(6) Uani 1 1 d . . . H46 H 0.5624 0.1107 0.8535 0.028 Uiso 1 1 calc R . . N1 N 0.90985(16) 0.29808(11) 0.91459(8) 0.0195(5) Uani 1 1 d . . . H1 H 0.9636 0.2846 0.9313 0.023 Uiso 1 1 calc R . . N2 N 0.98987(15) 0.29203(11) 0.78300(8) 0.0163(5) Uani 1 1 d . . . H2 H 0.9376 0.2984 0.7620 0.020 Uiso 1 1 calc R . . N3 N 0.95404(15) 0.21958(11) 0.68834(8) 0.0164(5) Uani 1 1 d . . . H3A H 0.9491 0.2027 0.7198 0.020 Uiso 1 1 calc R . . N4 N 0.74634(16) 0.16175(12) 0.60886(9) 0.0199(5) Uani 1 1 d . . . H4 H 0.7594 0.1809 0.5794 0.024 Uiso 1 1 calc R . . N5 N 0.76253(17) 0.37445(11) 0.63017(9) 0.0206(5) Uani 1 1 d . . . H5 H 0.7058 0.3671 0.6137 0.025 Uiso 1 1 calc R . . N6 N 0.72397(16) 0.27707(11) 0.74408(8) 0.0168(5) Uani 1 1 d . . . H6A H 0.7778 0.2795 0.7644 0.020 Uiso 1 1 calc R . . N7 N 0.80415(15) 0.16789(11) 0.80318(8) 0.0160(5) Uani 1 1 d . . . H7A H 0.8105 0.1736 0.7694 0.019 Uiso 1 1 calc R . . N8 N 1.03130(16) 0.10637(11) 0.85867(9) 0.0193(5) Uani 1 1 d . . . H8 H 1.0102 0.0967 0.8894 0.023 Uiso 1 1 calc R . . O1 O 0.83074(13) 0.31836(9) 0.83484(7) 0.0197(4) Uani 1 1 d . . . O2 O 0.79424(13) 0.14364(9) 0.69497(7) 0.0202(4) Uani 1 1 d . . . O3 O 0.86017(13) 0.35443(9) 0.70420(7) 0.0196(4) Uani 1 1 d . . . O4 O 0.98953(13) 0.14362(9) 0.77598(7) 0.0211(4) Uani 1 1 d . . . C47 C 0.9485(2) 0.47932(15) 0.75494(12) 0.0266(7) Uani 1 1 d . . . H47 H 0.9041 0.4435 0.7427 0.032 Uiso 1 1 calc R . . Cl1 Cl 1.03778(7) 0.48770(5) 0.70993(4) 0.0461(2) Uani 1 1 d . . . Cl2 Cl 1.00233(7) 0.45986(4) 0.81732(3) 0.0411(2) Uani 1 1 d . . . Cl3 Cl 0.88194(6) 0.55163(4) 0.75775(3) 0.03181(18) Uani 1 1 d . . . C48 C 0.2930(2) 0.10079(17) 0.69152(13) 0.0333(7) Uani 1 1 d . . . H48 H 0.3095 0.0549 0.7005 0.040 Uiso 1 1 calc R . . Cl4 Cl 0.34448(9) 0.12088(5) 0.63358(5) 0.0673(3) Uani 1 1 d . . . Cl5 Cl 0.16841(6) 0.10810(5) 0.68405(5) 0.0512(2) Uani 1 1 d . . . Cl6 Cl 0.33877(8) 0.15031(5) 0.74389(4) 0.0604(3) Uani 1 1 d . . . C49 C 0.6329(2) 0.49074(15) 0.77845(12) 0.0281(7) Uani 1 1 d . . . H49 H 0.6689 0.5324 0.7828 0.034 Uiso 1 1 calc R . . Cl7 Cl 0.70613(6) 0.42770(4) 0.80546(3) 0.03215(18) Uani 1 1 d . . . Cl8 Cl 0.52731(6) 0.49654(5) 0.81155(4) 0.0464(2) Uani 1 1 d . . . Cl9 Cl 0.60492(6) 0.47650(4) 0.71055(3) 0.03643(19) Uani 1 1 d . . . C50 C 0.7379(3) 0.06583(18) 0.42680(13) 0.0408(9) Uani 1 1 d . . . H50 H 0.7498 0.1107 0.4403 0.049 Uiso 1 1 calc R . . Cl10 Cl 0.81623(9) 0.01405(7) 0.46245(5) 0.0732(4) Uani 1 1 d . . . Cl11 Cl 0.61836(8) 0.04552(6) 0.43580(4) 0.0610(3) Uani 1 1 d . . . Cl12 Cl 0.75964(8) 0.06451(5) 0.35928(4) 0.0525(3) Uani 1 1 d . . . C51 C 0.1657(3) 0.4449(2) 0.53526(14) 0.0425(9) Uani 1 1 d . . . H51 H 0.1645 0.4909 0.5230 0.051 Uiso 1 1 calc R . . Cl13 Cl 0.12828(8) 0.44467(5) 0.59898(4) 0.0531(3) Uani 1 1 d . . . Cl14 Cl 0.08482(7) 0.40187(6) 0.49233(4) 0.0619(3) Uani 1 1 d . . . Cl15 Cl 0.28270(7) 0.41760(5) 0.53354(4) 0.0525(2) Uani 1 1 d . . . C52 C 0.0136(3) 0.1588(2) 0.47976(16) 0.0530(11) Uani 0.52(4) 1 d P A 1 H52A H -0.0577 0.1625 0.4791 0.064 Uiso 0.52(4) 1 calc PR A 1 Cl16 Cl 0.0629(13) 0.1263(6) 0.5413(4) 0.068(3) Uani 0.52(4) 1 d P A 1 C53 C 0.0136(3) 0.1588(2) 0.47976(16) 0.0530(11) Uani 0.48(4) 1 d P A 2 H53 H -0.0562 0.1674 0.4713 0.064 Uiso 0.48(4) 1 calc PR A 2 Cl17 Cl 0.0181(17) 0.1106(6) 0.5364(2) 0.079(3) Uani 0.48(4) 1 d P A 2 Cl18 Cl 0.04739(8) 0.11193(6) 0.42641(4) 0.0664(3) Uani 1 1 d . . . Cl19 Cl 0.06770(7) 0.23583(6) 0.47998(4) 0.0613(3) Uani 1 1 d . . . O1W O 0.55329(16) 0.27640(12) 0.47357(9) 0.0347(5) Uani 1 1 d D . . H1WA H 0.541(2) 0.3032(16) 0.4961(13) 0.052 Uiso 1 1 d D . . H1WB H 0.6073(17) 0.2621(18) 0.4815(14) 0.052 Uiso 1 1 d D . . O2W O 0.4695(2) 0.45169(12) 0.44907(9) 0.0396(6) Uani 1 1 d D . . H2WA H 0.488(3) 0.4428(17) 0.4810(9) 0.059 Uiso 1 1 d D . . H2WB H 0.469(3) 0.4923(9) 0.4482(14) 0.059 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02357(15) 0.03120(17) 0.01798(13) 0.00068(12) -0.00013(11) -0.00153(12) Br2 0.03555(18) 0.03298(19) 0.02404(15) 0.00556(13) -0.00196(12) 0.00805(14) C1 0.0259(16) 0.044(2) 0.0200(14) -0.0002(14) 0.0027(12) 0.0007(14) C2 0.0387(19) 0.038(2) 0.0360(18) -0.0063(15) 0.0083(15) 0.0061(16) C3 0.0184(14) 0.0310(17) 0.0202(14) -0.0044(12) 0.0015(11) 0.0013(12) C4 0.0220(14) 0.0114(14) 0.0195(13) -0.0006(11) -0.0017(11) -0.0014(11) C5 0.0205(14) 0.0135(14) 0.0171(13) -0.0004(11) -0.0012(10) -0.0025(11) C6 0.0202(14) 0.0206(15) 0.0190(13) 0.0031(11) -0.0048(11) -0.0026(12) C7 0.0181(14) 0.0206(16) 0.0220(14) 0.0024(11) -0.0020(11) -0.0008(11) C8 0.0165(13) 0.0151(14) 0.0211(13) 0.0007(11) -0.0001(11) -0.0023(11) C9 0.0180(13) 0.0138(14) 0.0214(13) 0.0017(11) 0.0018(11) 0.0036(11) C10 0.0163(13) 0.0179(15) 0.0198(13) -0.0009(11) 0.0017(11) 0.0005(11) C11 0.0234(14) 0.0201(15) 0.0167(13) 0.0023(11) 0.0032(11) -0.0018(12) C12 0.0259(15) 0.0223(16) 0.0140(13) 0.0014(11) -0.0006(11) -0.0007(12) C13 0.0204(14) 0.0150(14) 0.0180(13) -0.0017(11) -0.0006(11) 0.0030(11) C14 0.0217(14) 0.0132(14) 0.0167(13) -0.0024(11) 0.0012(11) 0.0024(11) C15 0.0248(15) 0.0300(17) 0.0160(13) 0.0016(12) -0.0004(11) -0.0086(13) C16 0.0245(16) 0.038(2) 0.0277(16) 0.0003(14) -0.0023(13) -0.0079(14) C17 0.044(2) 0.0279(19) 0.0354(18) 0.0016(14) -0.0050(15) -0.0094(15) C18 0.0195(14) 0.0188(15) 0.0218(14) 0.0053(11) 0.0003(11) 0.0014(11) C19 0.0233(15) 0.0250(17) 0.0219(14) 0.0043(12) -0.0007(11) -0.0012(12) C20 0.0254(16) 0.0246(17) 0.0345(17) 0.0066(13) -0.0022(13) -0.0060(13) C21 0.0191(15) 0.0325(19) 0.0438(19) 0.0160(15) 0.0070(13) 0.0000(13) C22 0.0272(16) 0.0306(18) 0.0325(17) 0.0059(14) 0.0098(13) 0.0064(14) C23 0.0243(15) 0.0217(16) 0.0262(15) 0.0027(12) 0.0027(12) 0.0022(12) C24 0.045(2) 0.0235(17) 0.0263(16) 0.0016(13) 0.0016(14) -0.0075(14) C25 0.0433(19) 0.0249(18) 0.0247(15) 0.0068(13) 0.0110(14) 0.0017(14) C26 0.0247(15) 0.0235(16) 0.0213(14) 0.0070(12) 0.0017(11) -0.0019(12) C27 0.0212(14) 0.0125(14) 0.0171(13) -0.0008(10) 0.0011(11) 0.0039(11) C28 0.0209(14) 0.0146(14) 0.0174(13) -0.0013(11) 0.0019(11) 0.0039(11) C29 0.0236(15) 0.0216(16) 0.0167(13) 0.0018(11) -0.0047(11) 0.0020(12) C30 0.0188(14) 0.0225(16) 0.0240(14) 0.0026(12) -0.0005(11) -0.0008(12) C31 0.0178(13) 0.0159(14) 0.0190(13) -0.0007(11) 0.0015(10) 0.0024(11) C32 0.0179(13) 0.0155(14) 0.0193(13) -0.0022(11) 0.0003(10) -0.0001(11) C33 0.0192(14) 0.0125(14) 0.0202(13) -0.0004(11) 0.0027(11) -0.0003(11) C34 0.0217(14) 0.0215(16) 0.0174(13) 0.0025(11) 0.0034(11) -0.0026(12) C35 0.0240(15) 0.0217(16) 0.0164(13) 0.0043(11) -0.0014(11) -0.0002(12) C36 0.0217(14) 0.0121(14) 0.0176(13) 0.0012(10) -0.0020(11) -0.0004(11) C37 0.0211(14) 0.0122(14) 0.0222(14) -0.0012(11) -0.0020(11) -0.0011(11) C38 0.0158(14) 0.0222(16) 0.0309(15) 0.0030(12) -0.0023(12) 0.0024(12) C39 0.0227(16) 0.0297(18) 0.0410(18) -0.0009(14) -0.0096(14) 0.0033(13) C40 0.0252(16) 0.0311(19) 0.0396(18) -0.0046(15) -0.0044(14) 0.0090(14) C41 0.0172(13) 0.0234(16) 0.0172(13) -0.0007(11) -0.0012(11) 0.0028(11) C42 0.0226(15) 0.0250(17) 0.0235(14) -0.0001(12) -0.0012(12) 0.0005(12) C43 0.0205(15) 0.0322(18) 0.0307(16) -0.0077(14) 0.0001(12) 0.0058(13) C44 0.0200(15) 0.044(2) 0.0295(16) -0.0055(14) 0.0067(12) -0.0017(14) C45 0.0253(16) 0.0358(19) 0.0256(15) 0.0056(13) 0.0050(12) -0.0018(14) C46 0.0214(15) 0.0263(17) 0.0209(14) 0.0029(12) -0.0011(11) 0.0014(12) N1 0.0169(11) 0.0247(14) 0.0165(11) 0.0005(9) -0.0015(9) 0.0020(10) N2 0.0149(11) 0.0185(13) 0.0151(11) 0.0006(9) -0.0020(9) 0.0001(9) N3 0.0189(11) 0.0165(12) 0.0137(10) 0.0001(9) 0.0013(9) 0.0007(9) N4 0.0207(12) 0.0235(13) 0.0155(11) 0.0019(9) 0.0015(9) -0.0045(10) N5 0.0209(12) 0.0201(13) 0.0201(12) 0.0033(10) -0.0024(9) -0.0021(10) N6 0.0159(11) 0.0171(12) 0.0171(11) 0.0013(9) -0.0012(9) 0.0015(9) N7 0.0173(11) 0.0162(12) 0.0144(10) 0.0026(9) 0.0008(9) 0.0016(9) N8 0.0185(12) 0.0189(13) 0.0198(11) 0.0020(9) -0.0026(9) 0.0015(10) O1 0.0183(10) 0.0218(11) 0.0183(9) -0.0004(8) -0.0026(8) 0.0034(8) O2 0.0245(10) 0.0202(11) 0.0154(9) 0.0024(8) -0.0005(8) -0.0013(8) O3 0.0201(10) 0.0194(11) 0.0187(9) 0.0004(8) -0.0019(8) 0.0007(8) O4 0.0218(10) 0.0214(11) 0.0203(10) 0.0037(8) 0.0023(8) 0.0037(8) C47 0.0284(16) 0.0232(17) 0.0280(15) -0.0053(13) 0.0005(13) 0.0014(13) Cl1 0.0426(5) 0.0518(6) 0.0461(5) -0.0062(4) 0.0178(4) 0.0067(4) Cl2 0.0501(5) 0.0355(5) 0.0357(4) 0.0034(4) -0.0092(4) 0.0052(4) Cl3 0.0398(4) 0.0258(4) 0.0299(4) -0.0028(3) 0.0038(3) 0.0078(3) C48 0.0296(17) 0.0282(18) 0.0425(19) 0.0026(15) 0.0044(14) 0.0008(14) Cl4 0.0941(9) 0.0434(6) 0.0723(7) 0.0009(5) 0.0549(7) 0.0084(6) Cl5 0.0278(4) 0.0416(6) 0.0836(7) -0.0007(5) 0.0006(4) -0.0048(4) Cl6 0.0672(7) 0.0543(7) 0.0548(6) -0.0023(5) -0.0264(5) -0.0071(5) C49 0.0301(16) 0.0220(17) 0.0323(16) 0.0005(13) 0.0037(13) 0.0086(13) Cl7 0.0337(4) 0.0254(4) 0.0360(4) -0.0007(3) -0.0056(3) 0.0094(3) Cl8 0.0394(5) 0.0614(6) 0.0399(5) 0.0086(4) 0.0121(4) 0.0217(4) Cl9 0.0414(5) 0.0378(5) 0.0297(4) 0.0026(3) 0.0004(3) 0.0129(4) C50 0.056(2) 0.031(2) 0.0337(18) -0.0019(15) -0.0048(16) 0.0041(17) Cl10 0.0704(7) 0.0834(9) 0.0662(7) 0.0379(6) 0.0086(6) 0.0282(7) Cl11 0.0557(6) 0.0885(9) 0.0379(5) -0.0166(5) -0.0019(4) -0.0055(6) Cl12 0.0756(7) 0.0434(6) 0.0381(5) 0.0024(4) 0.0035(5) -0.0096(5) C51 0.041(2) 0.052(2) 0.0363(19) 0.0027(17) 0.0076(16) -0.0021(17) Cl13 0.0681(7) 0.0557(6) 0.0385(5) -0.0171(4) 0.0220(5) -0.0197(5) Cl14 0.0495(6) 0.0995(9) 0.0377(5) -0.0197(5) 0.0089(4) -0.0247(6) Cl15 0.0407(5) 0.0532(6) 0.0648(6) -0.0109(5) 0.0111(5) 0.0050(4) C52 0.043(2) 0.065(3) 0.052(2) 0.008(2) 0.0108(18) 0.028(2) Cl16 0.097(6) 0.062(3) 0.046(2) 0.0192(17) 0.018(3) 0.044(3) C53 0.043(2) 0.065(3) 0.052(2) 0.008(2) 0.0108(18) 0.028(2) Cl17 0.109(8) 0.070(3) 0.0560(18) -0.0076(19) -0.002(3) 0.046(4) Cl18 0.0637(7) 0.0820(9) 0.0530(6) -0.0119(6) 0.0020(5) 0.0273(6) Cl19 0.0390(5) 0.0896(9) 0.0553(6) -0.0123(6) 0.0032(4) -0.0106(5) O1W 0.0287(12) 0.0408(15) 0.0337(13) -0.0118(11) -0.0033(10) -0.0001(11) O2W 0.0629(17) 0.0303(13) 0.0239(11) -0.0056(10) -0.0067(11) -0.0066(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C3 1.520(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.513(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N1 1.467(3) . ? C3 H3 1.0000 . ? C4 O1 1.241(3) . ? C4 N1 1.330(3) . ? C4 C5 1.485(4) . ? C5 N2 1.350(3) . ? C5 C6 1.395(4) . ? C6 C7 1.386(4) . ? C6 H6 0.9500 . ? C7 C8 1.403(4) . ? C7 H7 0.9500 . ? C8 N2 1.380(3) . ? C8 C9 1.418(4) . ? C9 C10 1.408(4) . ? C9 C18 1.459(4) . ? C10 N3 1.386(3) . ? C10 C11 1.407(4) . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C13 1.406(4) . ? C12 H12 0.9500 . ? C13 N3 1.341(3) . ? C13 C14 1.484(4) . ? C14 O2 1.245(3) . ? C14 N4 1.330(3) . ? C15 N4 1.470(4) . ? C15 C17 1.510(5) . ? C15 C16 1.520(4) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.404(4) . ? C18 C23 1.407(4) . ? C19 C20 1.385(4) . ? C19 H19 0.9500 . ? C20 C21 1.384(5) . ? C20 H20 0.9500 . ? C21 C22 1.387(5) . ? C21 H21 0.9500 . ? C22 C23 1.384(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C26 1.520(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.519(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 N5 1.468(4) . ? C26 H26 1.0000 . ? C27 O3 1.242(3) . ? C27 N5 1.331(3) . ? C27 C28 1.478(4) . ? C28 N6 1.349(3) . ? C28 C29 1.395(4) . ? C29 C30 1.382(4) . ? C29 H29 0.9500 . ? C30 C31 1.402(4) . ? C30 H30 0.9500 . ? C31 N6 1.378(3) . ? C31 C32 1.407(4) . ? C32 C33 1.399(4) . ? C32 C41 1.461(4) . ? C33 N7 1.390(3) . ? C33 C34 1.416(4) . ? C34 C35 1.372(4) . ? C34 H34 0.9500 . ? C35 C36 1.413(4) . ? C35 H35 0.9500 . ? C36 N7 1.343(3) . ? C36 C37 1.490(4) . ? C37 O4 1.238(3) . ? C37 N8 1.328(3) . ? C38 N8 1.465(4) . ? C38 C39 1.518(4) . ? C38 C40 1.519(4) . ? C38 H38 1.0000 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C46 1.399(4) . ? C41 C42 1.405(4) . ? C42 C43 1.384(4) . ? C42 H42 0.9500 . ? C43 C44 1.387(5) . ? C43 H43 0.9500 . ? C44 C45 1.387(5) . ? C44 H44 0.9500 . ? C45 C46 1.379(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? N3 H3A 0.8800 . ? N4 H4 0.8800 . ? N5 H5 0.8800 . ? N6 H6A 0.8800 . ? N7 H7A 0.8800 . ? N8 H8 0.8800 . ? C47 Cl2 1.748(3) . ? C47 Cl3 1.767(3) . ? C47 Cl1 1.769(3) . ? C47 H47 1.0000 . ? C48 Cl4 1.742(3) . ? C48 Cl5 1.745(3) . ? C48 Cl6 1.760(4) . ? C48 H48 1.0000 . ? C49 Cl8 1.762(3) . ? C49 Cl7 1.764(3) . ? C49 Cl9 1.765(3) . ? C49 H49 1.0000 . ? C50 Cl10 1.736(4) . ? C50 Cl11 1.757(4) . ? C50 Cl12 1.769(4) . ? C50 H50 1.0000 . ? C51 Cl15 1.735(4) . ? C51 Cl13 1.743(4) . ? C51 Cl14 1.752(4) . ? C51 H51 1.0000 . ? C52 Cl18 1.763(4) . ? C52 Cl19 1.765(5) . ? C52 Cl16 1.790(10) . ? C52 H52A 1.0000 . ? O1W H1WA 0.825(18) . ? O1W H1WB 0.821(18) . ? O2W H2WA 0.853(18) . ? O2W H2WB 0.841(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C2 110.0(2) . . ? N1 C3 C1 109.5(2) . . ? C2 C3 C1 112.4(3) . . ? N1 C3 H3 108.3 . . ? C2 C3 H3 108.3 . . ? C1 C3 H3 108.3 . . ? O1 C4 N1 124.0(3) . . ? O1 C4 C5 119.1(2) . . ? N1 C4 C5 116.9(2) . . ? N2 C5 C6 108.4(2) . . ? N2 C5 C4 118.3(2) . . ? C6 C5 C4 133.2(2) . . ? C7 C6 C5 107.4(2) . . ? C7 C6 H6 126.3 . . ? C5 C6 H6 126.3 . . ? C6 C7 C8 107.7(2) . . ? C6 C7 H7 126.1 . . ? C8 C7 H7 126.1 . . ? N2 C8 C7 106.9(2) . . ? N2 C8 C9 122.4(2) . . ? C7 C8 C9 130.6(3) . . ? C10 C9 C8 119.6(2) . . ? C10 C9 C18 121.5(2) . . ? C8 C9 C18 118.9(2) . . ? N3 C10 C11 106.9(2) . . ? N3 C10 C9 121.7(2) . . ? C11 C10 C9 131.2(3) . . ? C12 C11 C10 107.8(2) . . ? C12 C11 H11 126.1 . . ? C10 C11 H11 126.1 . . ? C11 C12 C13 107.3(2) . . ? C11 C12 H12 126.4 . . ? C13 C12 H12 126.4 . . ? N3 C13 C12 108.6(2) . . ? N3 C13 C14 118.8(2) . . ? C12 C13 C14 132.6(2) . . ? O2 C14 N4 123.7(3) . . ? O2 C14 C13 119.7(2) . . ? N4 C14 C13 116.6(2) . . ? N4 C15 C17 110.2(3) . . ? N4 C15 C16 109.6(2) . . ? C17 C15 C16 112.0(3) . . ? N4 C15 H15 108.3 . . ? C17 C15 H15 108.3 . . ? C16 C15 H15 108.3 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 118.8(3) . . ? C19 C18 C9 119.6(3) . . ? C23 C18 C9 121.7(3) . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 120.2(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 120.1(3) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? C26 C24 H24A 109.5 . . ? C26 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C26 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N5 C26 C25 109.2(2) . . ? N5 C26 C24 110.1(2) . . ? C25 C26 C24 111.7(2) . . ? N5 C26 H26 108.6 . . ? C25 C26 H26 108.6 . . ? C24 C26 H26 108.6 . . ? O3 C27 N5 124.2(3) . . ? O3 C27 C28 119.8(2) . . ? N5 C27 C28 116.0(2) . . ? N6 C28 C29 108.2(2) . . ? N6 C28 C27 118.7(2) . . ? C29 C28 C27 133.1(2) . . ? C30 C29 C28 107.6(2) . . ? C30 C29 H29 126.2 . . ? C28 C29 H29 126.2 . . ? C29 C30 C31 107.6(2) . . ? C29 C30 H30 126.2 . . ? C31 C30 H30 126.2 . . ? N6 C31 C30 107.1(2) . . ? N6 C31 C32 122.4(2) . . ? C30 C31 C32 130.4(3) . . ? C33 C32 C31 121.2(2) . . ? C33 C32 C41 119.1(2) . . ? C31 C32 C41 119.6(2) . . ? N7 C33 C32 123.7(2) . . ? N7 C33 C34 106.5(2) . . ? C32 C33 C34 129.5(2) . . ? C35 C34 C33 108.0(2) . . ? C35 C34 H34 126.0 . . ? C33 C34 H34 126.0 . . ? C34 C35 C36 107.4(2) . . ? C34 C35 H35 126.3 . . ? C36 C35 H35 126.3 . . ? N7 C36 C35 108.5(2) . . ? N7 C36 C37 119.7(2) . . ? C35 C36 C37 131.8(2) . . ? O4 C37 N8 124.7(3) . . ? O4 C37 C36 120.3(2) . . ? N8 C37 C36 115.0(2) . . ? N8 C38 C39 107.4(2) . . ? N8 C38 C40 111.3(2) . . ? C39 C38 C40 111.7(2) . . ? N8 C38 H38 108.8 . . ? C39 C38 H38 108.8 . . ? C40 C38 H38 108.8 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C40 H40A 109.5 . . ? C38 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C38 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C46 C41 C42 119.3(3) . . ? C46 C41 C32 121.5(3) . . ? C42 C41 C32 119.2(3) . . ? C43 C42 C41 119.8(3) . . ? C43 C42 H42 120.1 . . ? C41 C42 H42 120.1 . . ? C42 C43 C44 120.4(3) . . ? C42 C43 H43 119.8 . . ? C44 C43 H43 119.8 . . ? C45 C44 C43 119.9(3) . . ? C45 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C46 C45 C44 120.4(3) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C41 120.2(3) . . ? C45 C46 H46 119.9 . . ? C41 C46 H46 119.9 . . ? C4 N1 C3 122.0(2) . . ? C4 N1 H1 119.0 . . ? C3 N1 H1 119.0 . . ? C5 N2 C8 109.6(2) . . ? C5 N2 H2 125.2 . . ? C8 N2 H2 125.2 . . ? C13 N3 C10 109.4(2) . . ? C13 N3 H3A 125.3 . . ? C10 N3 H3A 125.3 . . ? C14 N4 C15 121.9(2) . . ? C14 N4 H4 119.1 . . ? C15 N4 H4 119.1 . . ? C27 N5 C26 123.4(2) . . ? C27 N5 H5 118.3 . . ? C26 N5 H5 118.3 . . ? C28 N6 C31 109.5(2) . . ? C28 N6 H6A 125.3 . . ? C31 N6 H6A 125.3 . . ? C36 N7 C33 109.5(2) . . ? C36 N7 H7A 125.2 . . ? C33 N7 H7A 125.2 . . ? C37 N8 C38 123.0(2) . . ? C37 N8 H8 118.5 . . ? C38 N8 H8 118.5 . . ? Cl2 C47 Cl3 110.38(16) . . ? Cl2 C47 Cl1 109.61(17) . . ? Cl3 C47 Cl1 110.16(17) . . ? Cl2 C47 H47 108.9 . . ? Cl3 C47 H47 108.9 . . ? Cl1 C47 H47 108.9 . . ? Cl4 C48 Cl5 111.35(19) . . ? Cl4 C48 Cl6 110.61(19) . . ? Cl5 C48 Cl6 109.35(19) . . ? Cl4 C48 H48 108.5 . . ? Cl5 C48 H48 108.5 . . ? Cl6 C48 H48 108.5 . . ? Cl8 C49 Cl7 110.31(17) . . ? Cl8 C49 Cl9 110.54(17) . . ? Cl7 C49 Cl9 109.52(16) . . ? Cl8 C49 H49 108.8 . . ? Cl7 C49 H49 108.8 . . ? Cl9 C49 H49 108.8 . . ? Cl10 C50 Cl11 110.6(2) . . ? Cl10 C50 Cl12 110.3(2) . . ? Cl11 C50 Cl12 111.27(19) . . ? Cl10 C50 H50 108.2 . . ? Cl11 C50 H50 108.2 . . ? Cl12 C50 H50 108.2 . . ? Cl15 C51 Cl13 112.1(2) . . ? Cl15 C51 Cl14 112.4(2) . . ? Cl13 C51 Cl14 110.5(2) . . ? Cl15 C51 H51 107.1 . . ? Cl13 C51 H51 107.1 . . ? Cl14 C51 H51 107.1 . . ? Cl18 C52 Cl19 111.0(2) . . ? Cl18 C52 Cl16 111.1(3) . . ? Cl19 C52 Cl16 101.6(7) . . ? Cl18 C52 H52A 110.9 . . ? Cl19 C52 H52A 110.9 . . ? Cl16 C52 H52A 110.9 . . ? H1WA O1W H1WB 108(3) . . ? H2WA O2W H2WB 104(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C4 C5 N2 -2.5(4) . . . . ? N1 C4 C5 N2 178.1(2) . . . . ? O1 C4 C5 C6 173.5(3) . . . . ? N1 C4 C5 C6 -5.9(5) . . . . ? N2 C5 C6 C7 1.8(3) . . . . ? C4 C5 C6 C7 -174.5(3) . . . . ? C5 C6 C7 C8 -1.3(3) . . . . ? C6 C7 C8 N2 0.3(3) . . . . ? C6 C7 C8 C9 -177.2(3) . . . . ? N2 C8 C9 C10 -29.8(4) . . . . ? C7 C8 C9 C10 147.4(3) . . . . ? N2 C8 C9 C18 150.0(3) . . . . ? C7 C8 C9 C18 -32.8(4) . . . . ? C8 C9 C10 N3 -22.5(4) . . . . ? C18 C9 C10 N3 157.7(3) . . . . ? C8 C9 C10 C11 151.7(3) . . . . ? C18 C9 C10 C11 -28.1(5) . . . . ? N3 C10 C11 C12 0.9(3) . . . . ? C9 C10 C11 C12 -174.0(3) . . . . ? C10 C11 C12 C13 -1.2(3) . . . . ? C11 C12 C13 N3 1.1(3) . . . . ? C11 C12 C13 C14 179.6(3) . . . . ? N3 C13 C14 O2 0.0(4) . . . . ? C12 C13 C14 O2 -178.4(3) . . . . ? N3 C13 C14 N4 178.8(2) . . . . ? C12 C13 C14 N4 0.4(4) . . . . ? C10 C9 C18 C19 150.0(3) . . . . ? C8 C9 C18 C19 -29.8(4) . . . . ? C10 C9 C18 C23 -30.1(4) . . . . ? C8 C9 C18 C23 150.1(3) . . . . ? C23 C18 C19 C20 -0.8(4) . . . . ? C9 C18 C19 C20 179.2(3) . . . . ? C18 C19 C20 C21 1.7(4) . . . . ? C19 C20 C21 C22 -1.6(5) . . . . ? C20 C21 C22 C23 0.6(5) . . . . ? C21 C22 C23 C18 0.3(5) . . . . ? C19 C18 C23 C22 -0.2(4) . . . . ? C9 C18 C23 C22 179.8(3) . . . . ? O3 C27 C28 N6 1.7(4) . . . . ? N5 C27 C28 N6 -178.5(2) . . . . ? O3 C27 C28 C29 179.7(3) . . . . ? N5 C27 C28 C29 -0.5(4) . . . . ? N6 C28 C29 C30 3.1(3) . . . . ? C27 C28 C29 C30 -175.1(3) . . . . ? C28 C29 C30 C31 -2.2(3) . . . . ? C29 C30 C31 N6 0.6(3) . . . . ? C29 C30 C31 C32 -176.3(3) . . . . ? N6 C31 C32 C33 -29.2(4) . . . . ? C30 C31 C32 C33 147.3(3) . . . . ? N6 C31 C32 C41 147.5(3) . . . . ? C30 C31 C32 C41 -36.0(4) . . . . ? C31 C32 C33 N7 -19.5(4) . . . . ? C41 C32 C33 N7 163.7(2) . . . . ? C31 C32 C33 C34 154.0(3) . . . . ? C41 C32 C33 C34 -22.8(4) . . . . ? N7 C33 C34 C35 0.7(3) . . . . ? C32 C33 C34 C35 -173.7(3) . . . . ? C33 C34 C35 C36 -1.2(3) . . . . ? C34 C35 C36 N7 1.2(3) . . . . ? C34 C35 C36 C37 177.8(3) . . . . ? N7 C36 C37 O4 5.4(4) . . . . ? C35 C36 C37 O4 -170.8(3) . . . . ? N7 C36 C37 N8 -176.8(2) . . . . ? C35 C36 C37 N8 7.0(4) . . . . ? C33 C32 C41 C46 -38.9(4) . . . . ? C31 C32 C41 C46 144.3(3) . . . . ? C33 C32 C41 C42 138.6(3) . . . . ? C31 C32 C41 C42 -38.2(4) . . . . ? C46 C41 C42 C43 2.6(4) . . . . ? C32 C41 C42 C43 -174.9(3) . . . . ? C41 C42 C43 C44 -2.5(4) . . . . ? C42 C43 C44 C45 0.7(5) . . . . ? C43 C44 C45 C46 1.0(5) . . . . ? C44 C45 C46 C41 -0.8(4) . . . . ? C42 C41 C46 C45 -1.0(4) . . . . ? C32 C41 C46 C45 176.5(3) . . . . ? O1 C4 N1 C3 -3.7(4) . . . . ? C5 C4 N1 C3 175.7(2) . . . . ? C2 C3 N1 C4 -82.2(3) . . . . ? C1 C3 N1 C4 153.8(3) . . . . ? C6 C5 N2 C8 -1.6(3) . . . . ? C4 C5 N2 C8 175.3(2) . . . . ? C7 C8 N2 C5 0.8(3) . . . . ? C9 C8 N2 C5 178.6(3) . . . . ? C12 C13 N3 C10 -0.5(3) . . . . ? C14 C13 N3 C10 -179.3(2) . . . . ? C11 C10 N3 C13 -0.2(3) . . . . ? C9 C10 N3 C13 175.2(2) . . . . ? O2 C14 N4 C15 -0.2(4) . . . . ? C13 C14 N4 C15 -178.9(2) . . . . ? C17 C15 N4 C14 -89.0(3) . . . . ? C16 C15 N4 C14 147.4(3) . . . . ? O3 C27 N5 C26 1.0(4) . . . . ? C28 C27 N5 C26 -178.8(2) . . . . ? C25 C26 N5 C27 138.8(3) . . . . ? C24 C26 N5 C27 -98.2(3) . . . . ? C29 C28 N6 C31 -2.7(3) . . . . ? C27 C28 N6 C31 175.8(2) . . . . ? C30 C31 N6 C28 1.3(3) . . . . ? C32 C31 N6 C28 178.5(2) . . . . ? C35 C36 N7 C33 -0.8(3) . . . . ? C37 C36 N7 C33 -177.8(2) . . . . ? C32 C33 N7 C36 174.9(3) . . . . ? C34 C33 N7 C36 0.1(3) . . . . ? O4 C37 N8 C38 3.6(4) . . . . ? C36 C37 N8 C38 -174.0(2) . . . . ? C39 C38 N8 C37 156.6(3) . . . . ? C40 C38 N8 C37 -80.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1W 0.88 2.03 2.858(3) 157.5 4_666 N2 H2 O3 0.88 2.10 2.897(3) 149.7 . N3 H3A O4 0.88 1.93 2.741(3) 152.1 . N4 H4 Br1 0.88 2.58 3.439(2) 167.0 . N5 H5 Br2 0.88 2.62 3.459(2) 159.2 . N6 H6A O1 0.88 2.05 2.782(3) 140.2 . N7 H7A O2 0.88 1.99 2.791(3) 151.2 . N8 H8 O2W 0.88 1.94 2.793(3) 162.0 4_666 O1W H1WA Br2 0.825(18) 2.53(2) 3.339(2) 169(3) . O1W H1WB Br1 0.821(18) 2.457(18) 3.262(2) 167(3) . O2W H2WA Br2 0.853(18) 2.442(18) 3.276(2) 166(3) . O2W H2WB Br2 0.841(18) 2.442(18) 3.279(3) 173(3) 3_666 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.264 _refine_diff_density_min -0.766 _refine_diff_density_rms 0.077 #===END data_thoi05b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(ipapdpm)CuCl' _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 Cl Cu N4 O2, C H4 O, 0.5(H2 O)' _chemical_formula_sum 'C24 H30 Cl Cu N4 O3.50' _chemical_formula_weight 529.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.850(4) _cell_length_b 16.419(5) _cell_length_c 25.676(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4996(3) _cell_formula_units_Z 8 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 4188 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.6 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 1.016 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8625 _exptl_absorpt_correction_T_max 0.9231 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex' _diffrn_measurement_method \w\p _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19863 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.34 _reflns_number_total 9634 _reflns_number_gt 7893 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v.1.00-2.1 (Bruker, 2006)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT v7.06A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All H atoms were located in a difference map, placed in idealized positions and treated with a riding model. The crystal was twinned by inversion. The batch scale factor refined to 40.0% (14) The isopropyl groups have some rotational freedom which leads to large thermal parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.4862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.399(12) _refine_ls_number_reflns 9634 _refine_ls_number_parameters 621 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.62330(4) 0.57477(3) 0.556200(18) 0.02365(12) Uani 1 1 d . . . C1 C 0.6772(3) 0.4107(2) 0.57001(15) 0.0234(9) Uani 1 1 d . . . C2 C 0.7005(3) 0.3341(2) 0.54641(16) 0.0244(9) Uani 1 1 d . . . H2 H 0.7148 0.2845 0.5635 0.029 Uiso 1 1 calc R . . C3 C 0.6976(3) 0.3472(3) 0.49391(17) 0.0276(9) Uani 1 1 d . . . H3 H 0.7105 0.3079 0.4680 0.033 Uiso 1 1 calc R . . C4 C 0.6716(3) 0.4316(3) 0.48512(15) 0.0241(9) Uani 1 1 d . . . C5 C 0.6414(3) 0.4727(2) 0.43861(16) 0.0236(8) Uani 1 1 d . . . C6 C 0.5918(3) 0.5511(2) 0.43954(16) 0.0216(8) Uani 1 1 d . . . C7 C 0.5533(3) 0.6030(2) 0.39837(15) 0.0241(9) Uani 1 1 d . . . H7 H 0.5568 0.5915 0.3625 0.029 Uiso 1 1 calc R . . C8 C 0.5100(3) 0.6729(2) 0.42070(15) 0.0245(9) Uani 1 1 d . . . H8 H 0.4779 0.7176 0.4033 0.029 Uiso 1 1 calc R . . C9 C 0.5240(3) 0.6634(2) 0.47564(15) 0.0219(9) Uani 1 1 d . . . C10 C 0.6574(3) 0.4295(3) 0.38859(15) 0.0259(9) Uani 1 1 d . . . C11 C 0.7606(4) 0.3927(3) 0.37680(18) 0.0338(11) Uani 1 1 d . . . H11 H 0.8211 0.3961 0.4004 0.041 Uiso 1 1 calc R . . C12 C 0.7732(4) 0.3510(3) 0.3300(2) 0.0431(12) Uani 1 1 d . . . H12 H 0.8429 0.3268 0.3219 0.052 Uiso 1 1 calc R . . C13 C 0.6846(5) 0.3447(3) 0.29534(19) 0.0466(13) Uani 1 1 d . . . H13 H 0.6941 0.3164 0.2638 0.056 Uiso 1 1 calc R . . C14 C 0.5814(4) 0.3804(3) 0.30703(18) 0.0385(11) Uani 1 1 d . . . H14 H 0.5207 0.3755 0.2836 0.046 Uiso 1 1 calc R . . C15 C 0.5675(3) 0.4230(3) 0.35310(15) 0.0294(9) Uani 1 1 d . . . H15 H 0.4979 0.4477 0.3607 0.035 Uiso 1 1 calc R . . C16 C 0.6588(3) 0.4414(2) 0.62311(16) 0.0240(9) Uani 1 1 d . . . C17 C 0.6605(4) 0.4187(3) 0.71789(16) 0.0412(12) Uani 1 1 d . . . H17 H 0.6046 0.4636 0.7187 0.049 Uiso 1 1 calc R . . C18 C 0.7686(6) 0.4481(5) 0.7399(3) 0.101(3) Uani 1 1 d . . . H18A H 0.8217 0.4032 0.7418 0.152 Uiso 1 1 calc R . . H18B H 0.7557 0.4696 0.7746 0.152 Uiso 1 1 calc R . . H18C H 0.7991 0.4906 0.7178 0.152 Uiso 1 1 calc R . . C19 C 0.6136(5) 0.3453(4) 0.7490(2) 0.0702(18) Uani 1 1 d . . . H19A H 0.5481 0.3234 0.7313 0.105 Uiso 1 1 calc R . . H19B H 0.5922 0.3631 0.7837 0.105 Uiso 1 1 calc R . . H19C H 0.6713 0.3036 0.7517 0.105 Uiso 1 1 calc R . . C20 C 0.5035(3) 0.7113(2) 0.52355(15) 0.0208(8) Uani 1 1 d . . . C21 C 0.4344(3) 0.8338(2) 0.56815(16) 0.0271(9) Uani 1 1 d . . . H21 H 0.4969 0.8235 0.5929 0.033 Uiso 1 1 calc R . . C22 C 0.3246(4) 0.8109(3) 0.59437(19) 0.0403(11) Uani 1 1 d . . . H22A H 0.2622 0.8217 0.5709 0.060 Uiso 1 1 calc R . . H22B H 0.3154 0.8428 0.6259 0.060 Uiso 1 1 calc R . . H22C H 0.3257 0.7534 0.6032 0.060 Uiso 1 1 calc R . . C23 C 0.4383(4) 0.9229(2) 0.55219(18) 0.0377(10) Uani 1 1 d . . . H23A H 0.5097 0.9343 0.5352 0.057 Uiso 1 1 calc R . . H23B H 0.4310 0.9570 0.5829 0.057 Uiso 1 1 calc R . . H23C H 0.3768 0.9344 0.5284 0.057 Uiso 1 1 calc R . . N1 N 0.6623(3) 0.46749(19) 0.53361(13) 0.0231(8) Uani 1 1 d . . . N2 N 0.5735(3) 0.5918(2) 0.48598(12) 0.0247(8) Uani 1 1 d . . . N3 N 0.4528(3) 0.78313(19) 0.52162(13) 0.0223(7) Uani 1 1 d . . . H3A H 0.4294 0.8011 0.4916 0.027 Uiso 1 1 calc R . . N4 N 0.6784(3) 0.3931(2) 0.66330(13) 0.0299(8) Uani 1 1 d . . . H4 H 0.7029 0.3441 0.6574 0.036 Uiso 1 1 calc R . . O1 O 0.6212(2) 0.51317(16) 0.62859(11) 0.0267(6) Uani 1 1 d . . . O2 O 0.5379(2) 0.68083(15) 0.56658(10) 0.0254(6) Uani 1 1 d . . . Cl1 Cl 0.81430(8) 0.63163(6) 0.57823(4) 0.0298(2) Uani 1 1 d . . . Cu2 Cu 0.30407(4) 0.42413(3) 0.438222(18) 0.02454(12) Uani 1 1 d . . . C24 C 0.4052(3) 0.3364(2) 0.51846(16) 0.0225(9) Uani 1 1 d . . . C25 C 0.4231(3) 0.3284(2) 0.57269(15) 0.0245(9) Uani 1 1 d . . . H25 H 0.4569 0.2843 0.5900 0.029 Uiso 1 1 calc R . . C26 C 0.3810(3) 0.3986(2) 0.59499(16) 0.0257(9) Uani 1 1 d . . . H26 H 0.3804 0.4110 0.6307 0.031 Uiso 1 1 calc R . . C27 C 0.3380(3) 0.4493(2) 0.55392(15) 0.0229(8) Uani 1 1 d . . . C28 C 0.2857(3) 0.5274(2) 0.55394(16) 0.0216(8) Uani 1 1 d . . . C29 C 0.2570(3) 0.5680(2) 0.50719(15) 0.0212(8) Uani 1 1 d . . . C30 C 0.2265(3) 0.6513(2) 0.49782(16) 0.0249(9) Uani 1 1 d . . . H30 H 0.2104 0.6906 0.5234 0.030 Uiso 1 1 calc R . . C31 C 0.2252(3) 0.6633(2) 0.44510(18) 0.0243(9) Uani 1 1 d . . . H31 H 0.2093 0.7123 0.4276 0.029 Uiso 1 1 calc R . . C32 C 0.2525(3) 0.5870(2) 0.42199(15) 0.0245(9) Uani 1 1 d . . . C33 C 0.2587(3) 0.5683(3) 0.60405(15) 0.0249(9) Uani 1 1 d . . . C34 C 0.3387(4) 0.5800(3) 0.64345(15) 0.0302(9) Uani 1 1 d . . . H34 H 0.4128 0.5609 0.6388 0.036 Uiso 1 1 calc R . . C35 C 0.3096(4) 0.6196(3) 0.68925(18) 0.0417(12) Uani 1 1 d . . . H35 H 0.3643 0.6287 0.7151 0.050 Uiso 1 1 calc R . . C36 C 0.1986(4) 0.6461(3) 0.69676(19) 0.0443(12) Uani 1 1 d . . . H36 H 0.1787 0.6722 0.7280 0.053 Uiso 1 1 calc R . . C37 C 0.1186(4) 0.6342(3) 0.65902(18) 0.0379(11) Uani 1 1 d . . . H37 H 0.0439 0.6514 0.6647 0.045 Uiso 1 1 calc R . . C38 C 0.1479(4) 0.5968(2) 0.61238(17) 0.0294(10) Uani 1 1 d . . . H38 H 0.0934 0.5905 0.5861 0.035 Uiso 1 1 calc R . . C39 C 0.4225(3) 0.2880(2) 0.47070(16) 0.0228(9) Uani 1 1 d . . . C40 C 0.4850(3) 0.1632(2) 0.42686(16) 0.0266(9) Uani 1 1 d . . . H40 H 0.4204 0.1733 0.4032 0.032 Uiso 1 1 calc R . . C41 C 0.4809(4) 0.0745(2) 0.4445(2) 0.0437(11) Uani 1 1 d . . . H41A H 0.5470 0.0624 0.4654 0.066 Uiso 1 1 calc R . . H41B H 0.4798 0.0392 0.4142 0.066 Uiso 1 1 calc R . . H41C H 0.4134 0.0655 0.4650 0.066 Uiso 1 1 calc R . . C42 C 0.5933(4) 0.1831(3) 0.3979(2) 0.0465(13) Uani 1 1 d . . . H42A H 0.5921 0.2397 0.3871 0.070 Uiso 1 1 calc R . . H42B H 0.5996 0.1484 0.3675 0.070 Uiso 1 1 calc R . . H42C H 0.6574 0.1739 0.4207 0.070 Uiso 1 1 calc R . . C43 C 0.2737(3) 0.5543(2) 0.36945(15) 0.0236(9) Uani 1 1 d . . . C44 C 0.2935(4) 0.5716(3) 0.27520(16) 0.0417(12) Uani 1 1 d . . . H44 H 0.2793 0.5121 0.2747 0.050 Uiso 1 1 calc R . . C45 C 0.4150(4) 0.5850(5) 0.2615(2) 0.077(2) Uani 1 1 d . . . H45A H 0.4320 0.6427 0.2633 0.116 Uiso 1 1 calc R . . H45B H 0.4291 0.5652 0.2265 0.116 Uiso 1 1 calc R . . H45C H 0.4625 0.5558 0.2860 0.116 Uiso 1 1 calc R . . C46 C 0.2163(5) 0.6105(3) 0.23560(19) 0.0526(14) Uani 1 1 d . . . H46A H 0.1385 0.5977 0.2440 0.079 Uiso 1 1 calc R . . H46B H 0.2340 0.5898 0.2012 0.079 Uiso 1 1 calc R . . H46C H 0.2268 0.6691 0.2361 0.079 Uiso 1 1 calc R . . N5 N 0.3559(3) 0.4084(2) 0.50810(13) 0.0245(8) Uani 1 1 d . . . N6 N 0.2714(3) 0.53199(18) 0.45938(12) 0.0216(7) Uani 1 1 d . . . N7 N 0.2675(3) 0.6013(2) 0.32773(13) 0.0286(8) Uani 1 1 d . . . H7A H 0.2472 0.6518 0.3316 0.034 Uiso 1 1 calc R . . N8 N 0.4727(3) 0.2160(2) 0.47287(13) 0.0260(8) Uani 1 1 d . . . H8A H 0.4993 0.1992 0.5026 0.031 Uiso 1 1 calc R . . O3 O 0.3870(2) 0.31763(15) 0.42790(10) 0.0266(6) Uani 1 1 d . . . O4 O 0.3006(2) 0.47964(16) 0.36598(11) 0.0267(6) Uani 1 1 d . . . Cl2 Cl 0.10702(9) 0.36740(6) 0.42951(5) 0.0383(3) Uani 1 1 d . . . C47 C 0.0294(6) 0.4478(4) 0.3042(3) 0.081(2) Uani 1 1 d . . . H47A H 0.0700 0.4839 0.3275 0.121 Uiso 1 1 calc R . . H47B H -0.0511 0.4533 0.3102 0.121 Uiso 1 1 calc R . . H47C H 0.0465 0.4621 0.2684 0.121 Uiso 1 1 calc R . . O5 O 0.0634(4) 0.3644(3) 0.31398(18) 0.0822(13) Uani 1 1 d . . . H5 H 0.0824 0.3594 0.3449 0.123 Uiso 1 1 calc R . . C48 C 0.6152(4) 0.6989(3) 0.68940(19) 0.0448(12) Uani 1 1 d . . . H48A H 0.5925 0.7251 0.7216 0.067 Uiso 1 1 calc R . . H48B H 0.6190 0.6404 0.6946 0.067 Uiso 1 1 calc R . . H48C H 0.5606 0.7110 0.6624 0.067 Uiso 1 1 calc R . . O6 O 0.7231(3) 0.72840(17) 0.67416(11) 0.0408(8) Uani 1 1 d . . . H6 H 0.7540 0.6946 0.6548 0.061 Uiso 1 1 calc R . . O7 O 0.2781(3) 0.26983(19) 0.32988(14) 0.0456(9) Uani 1 1 d D . . H1W H 0.217(2) 0.295(3) 0.333(2) 0.068 Uiso 1 1 d D . . H2W H 0.332(3) 0.295(3) 0.346(2) 0.068 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0314(3) 0.0187(2) 0.0208(2) -0.0009(2) -0.0014(2) 0.0043(2) C1 0.0187(18) 0.023(2) 0.028(2) 0.0001(18) -0.0006(17) 0.0024(15) C2 0.025(2) 0.018(2) 0.031(2) -0.0015(18) 0.0001(19) 0.0021(15) C3 0.028(2) 0.020(2) 0.035(2) -0.0043(19) -0.003(2) 0.0014(17) C4 0.024(2) 0.023(2) 0.0254(19) -0.0034(19) 0.0006(16) 0.0004(18) C5 0.0223(19) 0.026(2) 0.022(2) -0.0059(18) 0.0021(19) -0.0041(16) C6 0.0231(19) 0.0208(19) 0.0209(19) -0.0020(17) -0.0003(18) 0.0019(15) C7 0.025(2) 0.029(2) 0.0177(19) -0.0024(17) -0.0028(17) 0.0002(17) C8 0.023(2) 0.025(2) 0.025(2) 0.0035(18) -0.0020(18) 0.0016(16) C9 0.020(2) 0.023(2) 0.022(2) -0.0033(17) 0.0002(17) -0.0007(16) C10 0.028(2) 0.024(2) 0.026(2) -0.006(2) 0.0032(17) -0.0029(19) C11 0.030(2) 0.038(3) 0.033(2) -0.007(2) 0.003(2) -0.0007(19) C12 0.042(3) 0.046(3) 0.042(3) -0.009(2) 0.013(2) 0.011(2) C13 0.070(4) 0.041(3) 0.029(3) -0.011(2) 0.014(3) 0.004(3) C14 0.051(3) 0.037(3) 0.028(2) -0.008(2) -0.003(2) -0.002(2) C15 0.031(2) 0.030(2) 0.027(2) -0.001(2) -0.0007(18) 0.000(2) C16 0.022(2) 0.020(2) 0.029(2) 0.0024(18) -0.0023(17) -0.0011(16) C17 0.062(3) 0.040(3) 0.021(2) 0.004(2) 0.003(2) 0.010(3) C18 0.103(6) 0.142(8) 0.059(4) -0.041(5) -0.006(4) -0.047(5) C19 0.101(5) 0.066(4) 0.043(3) 0.011(3) 0.025(4) 0.002(4) C20 0.0197(19) 0.020(2) 0.0229(19) 0.0002(17) -0.0015(17) -0.0020(16) C21 0.030(2) 0.025(2) 0.025(2) -0.0050(18) -0.0073(19) 0.0064(17) C22 0.041(3) 0.038(3) 0.042(3) -0.009(2) 0.011(2) 0.005(2) C23 0.047(3) 0.023(2) 0.043(3) -0.004(2) -0.003(2) 0.005(2) N1 0.0297(18) 0.0159(17) 0.0236(18) -0.0022(14) -0.0012(15) 0.0032(14) N2 0.0294(18) 0.0233(19) 0.0214(17) -0.0006(15) -0.0028(15) 0.0066(15) N3 0.0254(17) 0.0186(16) 0.0228(17) -0.0024(15) -0.0020(15) 0.0044(14) N4 0.045(2) 0.0235(18) 0.0215(17) 0.0038(15) 0.0060(17) 0.0073(15) O1 0.0330(16) 0.0224(15) 0.0246(15) 0.0008(12) 0.0017(13) 0.0036(12) O2 0.0348(15) 0.0186(13) 0.0229(15) 0.0001(12) -0.0001(13) 0.0060(11) Cl1 0.0301(5) 0.0255(5) 0.0339(6) -0.0010(4) 0.0032(5) -0.0029(4) Cu2 0.0354(3) 0.0183(2) 0.0200(2) -0.0002(2) -0.0008(2) 0.0041(2) C24 0.023(2) 0.018(2) 0.027(2) 0.0023(17) 0.0014(17) -0.0001(16) C25 0.026(2) 0.025(2) 0.023(2) 0.0030(18) -0.0009(18) 0.0042(16) C26 0.027(2) 0.027(2) 0.023(2) 0.0005(17) 0.0027(18) 0.0035(17) C27 0.027(2) 0.0228(19) 0.0192(19) -0.0007(17) 0.0018(18) 0.0005(15) C28 0.0190(19) 0.026(2) 0.0195(19) -0.0014(18) 0.0026(17) -0.0038(15) C29 0.0201(19) 0.018(2) 0.0252(19) 0.0005(18) -0.0009(16) -0.0017(17) C30 0.025(2) 0.020(2) 0.030(2) -0.0065(18) 0.0049(18) 0.0009(17) C31 0.025(2) 0.0168(19) 0.031(2) 0.0009(19) 0.0016(19) 0.0000(15) C32 0.024(2) 0.023(2) 0.026(2) -0.0022(18) 0.0002(17) -0.0028(17) C33 0.030(2) 0.024(2) 0.0208(19) 0.0004(19) 0.0053(17) -0.0017(19) C34 0.032(2) 0.034(2) 0.024(2) -0.001(2) -0.0012(18) -0.001(2) C35 0.057(3) 0.044(3) 0.024(2) -0.004(2) -0.007(2) -0.011(2) C36 0.066(3) 0.040(3) 0.027(2) -0.009(2) 0.019(3) 0.001(3) C37 0.038(3) 0.037(3) 0.039(3) -0.004(2) 0.008(2) 0.001(2) C38 0.033(2) 0.025(2) 0.031(2) -0.0007(18) 0.0048(19) -0.0035(18) C39 0.0173(19) 0.021(2) 0.031(2) 0.0012(18) 0.0040(17) -0.0016(16) C40 0.031(2) 0.021(2) 0.028(2) -0.0061(18) 0.0032(19) 0.0030(16) C41 0.051(3) 0.024(2) 0.056(3) -0.004(3) -0.006(3) 0.004(2) C42 0.048(3) 0.040(3) 0.051(3) -0.014(3) 0.014(3) -0.002(2) C43 0.023(2) 0.024(2) 0.024(2) 0.0007(17) -0.0010(17) -0.0001(16) C44 0.064(3) 0.037(3) 0.024(2) 0.007(2) -0.004(2) 0.003(3) C45 0.057(4) 0.146(7) 0.030(3) -0.001(4) 0.002(3) 0.018(4) C46 0.070(4) 0.057(3) 0.031(3) 0.002(2) -0.011(3) -0.001(3) N5 0.0330(19) 0.0178(18) 0.0226(17) 0.0001(14) 0.0025(15) 0.0016(14) N6 0.0257(18) 0.0203(17) 0.0189(16) -0.0008(14) -0.0003(14) 0.0038(14) N7 0.042(2) 0.0225(18) 0.0211(17) 0.0008(15) -0.0004(16) 0.0054(15) N8 0.0265(18) 0.0239(18) 0.0275(18) -0.0007(16) -0.0035(16) 0.0023(15) O3 0.0347(16) 0.0196(14) 0.0255(15) -0.0023(12) -0.0016(13) 0.0032(12) O4 0.0309(16) 0.0244(15) 0.0247(15) 0.0005(13) -0.0008(13) 0.0034(12) Cl2 0.0349(6) 0.0298(6) 0.0502(7) 0.0081(5) 0.0023(5) -0.0035(4) C47 0.075(4) 0.070(5) 0.096(5) 0.015(4) 0.001(4) 0.002(4) O5 0.084(3) 0.096(4) 0.067(3) -0.007(3) -0.005(3) 0.007(3) C48 0.061(3) 0.043(3) 0.031(3) -0.006(2) -0.004(3) -0.004(2) O6 0.068(2) 0.0273(16) 0.0266(16) -0.0025(14) 0.0059(16) -0.0045(16) O7 0.061(2) 0.0329(19) 0.043(2) -0.0052(16) -0.003(2) -0.0028(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.911(3) . ? Cu1 N2 1.917(3) . ? Cu1 O2 2.031(2) . ? Cu1 O1 2.116(3) . ? Cu1 Cl1 2.5129(13) . ? C1 N1 1.332(5) . ? C1 C2 1.423(5) . ? C1 C16 1.470(5) . ? C2 C3 1.366(6) . ? C2 H2 0.9400 . ? C3 C4 1.437(6) . ? C3 H3 0.9400 . ? C4 N1 1.382(5) . ? C4 C5 1.418(5) . ? C5 C6 1.415(5) . ? C5 C10 1.480(5) . ? C6 N2 1.384(5) . ? C6 C7 1.432(5) . ? C7 C8 1.382(5) . ? C7 H7 0.9400 . ? C8 C9 1.429(5) . ? C8 H8 0.9400 . ? C9 N2 1.341(5) . ? C9 C20 1.480(5) . ? C10 C11 1.397(6) . ? C10 C15 1.406(5) . ? C11 C12 1.392(6) . ? C11 H11 0.9400 . ? C12 C13 1.380(7) . ? C12 H12 0.9400 . ? C13 C14 1.389(7) . ? C13 H13 0.9400 . ? C14 C15 1.384(6) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? C16 O1 1.267(4) . ? C16 N4 1.322(5) . ? C17 N4 1.479(5) . ? C17 C18 1.481(8) . ? C17 C19 1.549(7) . ? C17 H17 0.9900 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C20 O2 1.279(4) . ? C20 N3 1.325(5) . ? C21 N3 1.472(5) . ? C21 C22 1.513(6) . ? C21 C23 1.521(5) . ? C21 H21 0.9900 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? N3 H3A 0.8700 . ? N4 H4 0.8700 . ? Cu2 N6 1.893(3) . ? Cu2 N5 1.914(3) . ? Cu2 O3 2.023(3) . ? Cu2 O4 2.067(3) . ? Cu2 Cl2 2.5238(13) . ? C24 N5 1.344(5) . ? C24 C25 1.415(6) . ? C24 C39 1.476(6) . ? C25 C26 1.381(5) . ? C25 H25 0.9400 . ? C26 C27 1.436(5) . ? C26 H26 0.9400 . ? C27 N5 1.371(5) . ? C27 C28 1.424(5) . ? C28 C29 1.415(5) . ? C28 C33 1.487(5) . ? C29 N6 1.373(5) . ? C29 C30 1.435(5) . ? C30 C31 1.368(6) . ? C30 H30 0.9400 . ? C31 C32 1.424(5) . ? C31 H31 0.9400 . ? C32 N6 1.337(5) . ? C32 C43 1.473(5) . ? C33 C34 1.400(6) . ? C33 C38 1.410(6) . ? C34 C35 1.388(6) . ? C34 H34 0.9400 . ? C35 C36 1.399(7) . ? C35 H35 0.9400 . ? C36 C37 1.370(7) . ? C36 H36 0.9400 . ? C37 C38 1.390(6) . ? C37 H37 0.9400 . ? C38 H38 0.9400 . ? C39 O3 1.274(5) . ? C39 N8 1.324(5) . ? C40 N8 1.472(5) . ? C40 C42 1.519(6) . ? C40 C41 1.526(5) . ? C40 H40 0.9900 . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C41 H41C 0.9700 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C42 H42C 0.9700 . ? C43 O4 1.270(4) . ? C43 N7 1.322(5) . ? C44 N7 1.467(5) . ? C44 C45 1.498(7) . ? C44 C46 1.510(6) . ? C44 H44 0.9900 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C45 H45C 0.9700 . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C46 H46C 0.9700 . ? N7 H7A 0.8700 . ? N8 H8A 0.8700 . ? C47 O5 1.450(6) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C47 H47C 0.9700 . ? O5 H5 0.8300 . ? C48 O6 1.422(6) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C48 H48C 0.9700 . ? O6 H6 0.8300 . ? O7 H1W 0.840(19) . ? O7 H2W 0.859(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 85.60(14) . . ? N1 Cu1 O2 161.86(12) . . ? N2 Cu1 O2 81.11(12) . . ? N1 Cu1 O1 80.15(12) . . ? N2 Cu1 O1 153.11(13) . . ? O2 Cu1 O1 106.77(11) . . ? N1 Cu1 Cl1 101.12(10) . . ? N2 Cu1 Cl1 115.76(11) . . ? O2 Cu1 Cl1 95.77(8) . . ? O1 Cu1 Cl1 89.45(8) . . ? N1 C1 C2 110.2(3) . . ? N1 C1 C16 113.0(3) . . ? C2 C1 C16 136.6(4) . . ? C3 C2 C1 106.0(4) . . ? C3 C2 H2 127.0 . . ? C1 C2 H2 127.0 . . ? C2 C3 C4 108.2(4) . . ? C2 C3 H3 125.9 . . ? C4 C3 H3 125.9 . . ? N1 C4 C5 122.4(4) . . ? N1 C4 C3 106.6(3) . . ? C5 C4 C3 130.2(4) . . ? C6 C5 C4 121.6(4) . . ? C6 C5 C10 120.3(4) . . ? C4 C5 C10 118.1(3) . . ? N2 C6 C5 121.2(3) . . ? N2 C6 C7 107.4(3) . . ? C5 C6 C7 131.4(4) . . ? C8 C7 C6 107.8(3) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? C7 C8 C9 106.0(4) . . ? C7 C8 H8 127.0 . . ? C9 C8 H8 127.0 . . ? N2 C9 C8 110.0(3) . . ? N2 C9 C20 111.9(3) . . ? C8 C9 C20 138.0(4) . . ? C11 C10 C15 119.4(4) . . ? C11 C10 C5 120.5(4) . . ? C15 C10 C5 120.1(4) . . ? C12 C11 C10 119.6(4) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 120.7(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 120.0(4) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 120.1(4) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 120.1(4) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? O1 C16 N4 122.2(4) . . ? O1 C16 C1 118.3(4) . . ? N4 C16 C1 119.5(3) . . ? N4 C17 C18 109.3(4) . . ? N4 C17 C19 108.6(4) . . ? C18 C17 C19 111.4(5) . . ? N4 C17 H17 109.1 . . ? C18 C17 H17 109.1 . . ? C19 C17 H17 109.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 N3 121.6(4) . . ? O2 C20 C9 117.2(3) . . ? N3 C20 C9 121.1(3) . . ? N3 C21 C22 110.4(3) . . ? N3 C21 C23 108.7(3) . . ? C22 C21 C23 112.6(4) . . ? N3 C21 H21 108.3 . . ? C22 C21 H21 108.3 . . ? C23 C21 H21 108.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 N1 C4 108.9(3) . . ? C1 N1 Cu1 117.7(3) . . ? C4 N1 Cu1 133.3(3) . . ? C9 N2 C6 108.7(3) . . ? C9 N2 Cu1 116.6(3) . . ? C6 N2 Cu1 133.8(3) . . ? C20 N3 C21 122.7(3) . . ? C20 N3 H3A 118.7 . . ? C21 N3 H3A 118.7 . . ? C16 N4 C17 123.0(4) . . ? C16 N4 H4 118.5 . . ? C17 N4 H4 118.5 . . ? C16 O1 Cu1 110.0(3) . . ? C20 O2 Cu1 112.4(2) . . ? N6 Cu2 N5 85.60(14) . . ? N6 Cu2 O3 161.04(12) . . ? N5 Cu2 O3 81.37(12) . . ? N6 Cu2 O4 80.84(12) . . ? N5 Cu2 O4 155.12(13) . . ? O3 Cu2 O4 105.85(11) . . ? N6 Cu2 Cl2 100.45(10) . . ? N5 Cu2 Cl2 109.28(10) . . ? O3 Cu2 Cl2 96.83(8) . . ? O4 Cu2 Cl2 93.71(8) . . ? N5 C24 C25 110.0(4) . . ? N5 C24 C39 111.7(3) . . ? C25 C24 C39 138.3(4) . . ? C26 C25 C24 106.0(4) . . ? C26 C25 H25 127.0 . . ? C24 C25 H25 127.0 . . ? C25 C26 C27 107.9(4) . . ? C25 C26 H26 126.1 . . ? C27 C26 H26 126.1 . . ? N5 C27 C28 120.6(3) . . ? N5 C27 C26 106.9(3) . . ? C28 C27 C26 132.5(4) . . ? C29 C28 C27 121.9(4) . . ? C29 C28 C33 118.0(3) . . ? C27 C28 C33 120.1(4) . . ? N6 C29 C28 121.7(4) . . ? N6 C29 C30 107.0(3) . . ? C28 C29 C30 130.7(4) . . ? C31 C30 C29 107.8(4) . . ? C31 C30 H30 126.1 . . ? C29 C30 H30 126.1 . . ? C30 C31 C32 106.4(4) . . ? C30 C31 H31 126.8 . . ? C32 C31 H31 126.8 . . ? N6 C32 C31 109.5(3) . . ? N6 C32 C43 112.6(3) . . ? C31 C32 C43 137.8(4) . . ? C34 C33 C38 118.4(4) . . ? C34 C33 C28 122.8(4) . . ? C38 C33 C28 118.8(4) . . ? C35 C34 C33 120.6(4) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 119.7(4) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C37 C36 C35 120.6(4) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C36 C37 C38 119.9(4) . . ? C36 C37 H37 120.0 . . ? C38 C37 H37 120.0 . . ? C37 C38 C33 120.7(4) . . ? C37 C38 H38 119.7 . . ? C33 C38 H38 119.7 . . ? O3 C39 N8 121.7(4) . . ? O3 C39 C24 117.7(3) . . ? N8 C39 C24 120.6(4) . . ? N8 C40 C42 110.5(3) . . ? N8 C40 C41 108.7(4) . . ? C42 C40 C41 112.1(4) . . ? N8 C40 H40 108.5 . . ? C42 C40 H40 108.5 . . ? C41 C40 H40 108.5 . . ? C40 C41 H41A 109.5 . . ? C40 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C40 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C40 C42 H42A 109.5 . . ? C40 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C40 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O4 C43 N7 121.3(4) . . ? O4 C43 C32 117.3(3) . . ? N7 C43 C32 121.4(3) . . ? N7 C44 C45 111.6(4) . . ? N7 C44 C46 110.6(4) . . ? C45 C44 C46 111.2(4) . . ? N7 C44 H44 107.8 . . ? C45 C44 H44 107.8 . . ? C46 C44 H44 107.8 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C24 N5 C27 109.1(3) . . ? C24 N5 Cu2 116.3(3) . . ? C27 N5 Cu2 133.5(3) . . ? C32 N6 C29 109.3(3) . . ? C32 N6 Cu2 117.4(3) . . ? C29 N6 Cu2 133.2(3) . . ? C43 N7 C44 122.7(4) . . ? C43 N7 H7A 118.7 . . ? C44 N7 H7A 118.7 . . ? C39 N8 C40 122.4(3) . . ? C39 N8 H8A 118.8 . . ? C40 N8 H8A 118.8 . . ? C39 O3 Cu2 112.2(2) . . ? C43 O4 Cu2 111.6(2) . . ? O5 C47 H47A 109.5 . . ? O5 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? O5 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C47 O5 H5 109.5 . . ? O6 C48 H48A 109.5 . . ? O6 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? O6 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C48 O6 H6 109.5 . . ? H1W O7 H2W 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.7(4) . . . . ? C16 C1 C2 C3 174.7(4) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 N1 1.5(4) . . . . ? C2 C3 C4 C5 -168.5(4) . . . . ? N1 C4 C5 C6 -4.8(6) . . . . ? C3 C4 C5 C6 163.9(4) . . . . ? N1 C4 C5 C10 178.4(4) . . . . ? C3 C4 C5 C10 -12.9(6) . . . . ? C4 C5 C6 N2 1.8(6) . . . . ? C10 C5 C6 N2 178.5(3) . . . . ? C4 C5 C6 C7 -178.9(4) . . . . ? C10 C5 C6 C7 -2.2(6) . . . . ? N2 C6 C7 C8 -1.5(4) . . . . ? C5 C6 C7 C8 179.1(4) . . . . ? C6 C7 C8 C9 0.8(4) . . . . ? C7 C8 C9 N2 0.3(5) . . . . ? C7 C8 C9 C20 177.3(4) . . . . ? C6 C5 C10 C11 132.7(4) . . . . ? C4 C5 C10 C11 -50.5(6) . . . . ? C6 C5 C10 C15 -49.2(6) . . . . ? C4 C5 C10 C15 127.6(4) . . . . ? C15 C10 C11 C12 0.7(7) . . . . ? C5 C10 C11 C12 178.7(4) . . . . ? C10 C11 C12 C13 -0.8(7) . . . . ? C11 C12 C13 C14 0.0(8) . . . . ? C12 C13 C14 C15 0.8(7) . . . . ? C13 C14 C15 C10 -0.9(7) . . . . ? C11 C10 C15 C14 0.2(7) . . . . ? C5 C10 C15 C14 -177.9(4) . . . . ? N1 C1 C16 O1 6.8(5) . . . . ? C2 C1 C16 O1 -168.5(4) . . . . ? N1 C1 C16 N4 -175.3(3) . . . . ? C2 C1 C16 N4 9.5(7) . . . . ? N2 C9 C20 O2 2.5(5) . . . . ? C8 C9 C20 O2 -174.5(4) . . . . ? N2 C9 C20 N3 -178.4(3) . . . . ? C8 C9 C20 N3 4.6(7) . . . . ? C2 C1 N1 C4 1.7(4) . . . . ? C16 C1 N1 C4 -174.9(3) . . . . ? C2 C1 N1 Cu1 177.3(2) . . . . ? C16 C1 N1 Cu1 0.8(4) . . . . ? C5 C4 N1 C1 169.1(3) . . . . ? C3 C4 N1 C1 -1.9(4) . . . . ? C5 C4 N1 Cu1 -5.6(6) . . . . ? C3 C4 N1 Cu1 -176.6(3) . . . . ? N2 Cu1 N1 C1 -161.6(3) . . . . ? O2 Cu1 N1 C1 -118.7(4) . . . . ? O1 Cu1 N1 C1 -4.5(3) . . . . ? Cl1 Cu1 N1 C1 83.0(3) . . . . ? N2 Cu1 N1 C4 12.7(4) . . . . ? O2 Cu1 N1 C4 55.6(6) . . . . ? O1 Cu1 N1 C4 169.8(4) . . . . ? Cl1 Cu1 N1 C4 -102.7(4) . . . . ? C8 C9 N2 C6 -1.2(5) . . . . ? C20 C9 N2 C6 -179.1(3) . . . . ? C8 C9 N2 Cu1 169.8(3) . . . . ? C20 C9 N2 Cu1 -8.1(4) . . . . ? C5 C6 N2 C9 -178.9(3) . . . . ? C7 C6 N2 C9 1.7(4) . . . . ? C5 C6 N2 Cu1 12.3(6) . . . . ? C7 C6 N2 Cu1 -167.2(3) . . . . ? N1 Cu1 N2 C9 175.6(3) . . . . ? O2 Cu1 N2 C9 8.0(3) . . . . ? O1 Cu1 N2 C9 117.7(3) . . . . ? Cl1 Cu1 N2 C9 -84.2(3) . . . . ? N1 Cu1 N2 C6 -16.2(4) . . . . ? O2 Cu1 N2 C6 176.2(4) . . . . ? O1 Cu1 N2 C6 -74.1(5) . . . . ? Cl1 Cu1 N2 C6 84.0(4) . . . . ? O2 C20 N3 C21 1.3(6) . . . . ? C9 C20 N3 C21 -177.8(3) . . . . ? C22 C21 N3 C20 -87.4(5) . . . . ? C23 C21 N3 C20 148.6(4) . . . . ? O1 C16 N4 C17 -1.2(6) . . . . ? C1 C16 N4 C17 -179.0(4) . . . . ? C18 C17 N4 C16 -95.5(6) . . . . ? C19 C17 N4 C16 142.7(4) . . . . ? N4 C16 O1 Cu1 172.2(3) . . . . ? C1 C16 O1 Cu1 -10.0(4) . . . . ? N1 Cu1 O1 C16 7.9(3) . . . . ? N2 Cu1 O1 C16 66.9(4) . . . . ? O2 Cu1 O1 C16 170.7(2) . . . . ? Cl1 Cu1 O1 C16 -93.5(3) . . . . ? N3 C20 O2 Cu1 -175.3(3) . . . . ? C9 C20 O2 Cu1 3.8(4) . . . . ? N1 Cu1 O2 C20 -49.6(5) . . . . ? N2 Cu1 O2 C20 -6.3(3) . . . . ? O1 Cu1 O2 C20 -159.9(2) . . . . ? Cl1 Cu1 O2 C20 108.9(2) . . . . ? N5 C24 C25 C26 0.8(5) . . . . ? C39 C24 C25 C26 -177.4(4) . . . . ? C24 C25 C26 C27 -0.3(5) . . . . ? C25 C26 C27 N5 -0.3(4) . . . . ? C25 C26 C27 C28 -179.9(4) . . . . ? N5 C27 C28 C29 -4.1(6) . . . . ? C26 C27 C28 C29 175.5(4) . . . . ? N5 C27 C28 C33 175.3(3) . . . . ? C26 C27 C28 C33 -5.1(6) . . . . ? C27 C28 C29 N6 4.3(6) . . . . ? C33 C28 C29 N6 -175.1(3) . . . . ? C27 C28 C29 C30 -165.5(4) . . . . ? C33 C28 C29 C30 15.1(6) . . . . ? N6 C29 C30 C31 -1.0(4) . . . . ? C28 C29 C30 C31 170.0(4) . . . . ? C29 C30 C31 C32 1.2(4) . . . . ? C30 C31 C32 N6 -1.1(4) . . . . ? C30 C31 C32 C43 -175.1(4) . . . . ? C29 C28 C33 C34 -128.0(5) . . . . ? C27 C28 C33 C34 52.5(6) . . . . ? C29 C28 C33 C38 51.9(5) . . . . ? C27 C28 C33 C38 -127.6(4) . . . . ? C38 C33 C34 C35 -0.8(7) . . . . ? C28 C33 C34 C35 179.1(4) . . . . ? C33 C34 C35 C36 1.8(7) . . . . ? C34 C35 C36 C37 -0.9(8) . . . . ? C35 C36 C37 C38 -1.1(7) . . . . ? C36 C37 C38 C33 2.2(7) . . . . ? C34 C33 C38 C37 -1.2(6) . . . . ? C28 C33 C38 C37 178.9(4) . . . . ? N5 C24 C39 O3 -2.2(5) . . . . ? C25 C24 C39 O3 175.9(5) . . . . ? N5 C24 C39 N8 178.3(3) . . . . ? C25 C24 C39 N8 -3.6(7) . . . . ? N6 C32 C43 O4 3.4(5) . . . . ? C31 C32 C43 O4 177.4(4) . . . . ? N6 C32 C43 N7 -175.1(4) . . . . ? C31 C32 C43 N7 -1.1(7) . . . . ? C25 C24 N5 C27 -1.0(5) . . . . ? C39 C24 N5 C27 177.7(3) . . . . ? C25 C24 N5 Cu2 -171.0(3) . . . . ? C39 C24 N5 Cu2 7.7(4) . . . . ? C28 C27 N5 C24 -179.5(3) . . . . ? C26 C27 N5 C24 0.8(4) . . . . ? C28 C27 N5 Cu2 -11.9(6) . . . . ? C26 C27 N5 Cu2 168.4(3) . . . . ? N6 Cu2 N5 C24 -173.9(3) . . . . ? O3 Cu2 N5 C24 -7.7(3) . . . . ? O4 Cu2 N5 C24 -117.0(3) . . . . ? Cl2 Cu2 N5 C24 86.5(3) . . . . ? N6 Cu2 N5 C27 19.1(4) . . . . ? O3 Cu2 N5 C27 -174.7(4) . . . . ? O4 Cu2 N5 C27 76.1(5) . . . . ? Cl2 Cu2 N5 C27 -80.4(4) . . . . ? C31 C32 N6 C29 0.5(4) . . . . ? C43 C32 N6 C29 176.2(3) . . . . ? C31 C32 N6 Cu2 177.8(2) . . . . ? C43 C32 N6 Cu2 -6.5(4) . . . . ? C28 C29 N6 C32 -171.6(3) . . . . ? C30 C29 N6 C32 0.3(4) . . . . ? C28 C29 N6 Cu2 11.6(6) . . . . ? C30 C29 N6 Cu2 -176.4(3) . . . . ? N5 Cu2 N6 C32 164.6(3) . . . . ? O3 Cu2 N6 C32 118.0(4) . . . . ? O4 Cu2 N6 C32 5.6(3) . . . . ? Cl2 Cu2 N6 C32 -86.5(3) . . . . ? N5 Cu2 N6 C29 -18.9(4) . . . . ? O3 Cu2 N6 C29 -65.4(6) . . . . ? O4 Cu2 N6 C29 -177.9(4) . . . . ? Cl2 Cu2 N6 C29 90.0(3) . . . . ? O4 C43 N7 C44 -1.5(6) . . . . ? C32 C43 N7 C44 177.0(4) . . . . ? C45 C44 N7 C43 -91.7(6) . . . . ? C46 C44 N7 C43 143.9(4) . . . . ? O3 C39 N8 C40 -3.6(6) . . . . ? C24 C39 N8 C40 175.8(3) . . . . ? C42 C40 N8 C39 88.5(5) . . . . ? C41 C40 N8 C39 -148.1(4) . . . . ? N8 C39 O3 Cu2 175.6(3) . . . . ? C24 C39 O3 Cu2 -3.9(4) . . . . ? N6 Cu2 O3 C39 53.3(5) . . . . ? N5 Cu2 O3 C39 6.2(3) . . . . ? O4 Cu2 O3 C39 161.8(3) . . . . ? Cl2 Cu2 O3 C39 -102.3(3) . . . . ? N7 C43 O4 Cu2 179.4(3) . . . . ? C32 C43 O4 Cu2 0.9(4) . . . . ? N6 Cu2 O4 C43 -3.4(3) . . . . ? N5 Cu2 O4 C43 -61.3(4) . . . . ? O3 Cu2 O4 C43 -165.2(3) . . . . ? Cl2 Cu2 O4 C43 96.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A Cl1 0.87 2.51 3.350(3) 162.8 4_466 N4 H4 O7 0.87 2.10 2.930(5) 160.1 4_556 N7 H7A O6 0.87 1.99 2.846(4) 166.7 4_466 N8 H8A Cl2 0.87 2.42 3.270(4) 164.8 4_556 O5 H5 Cl2 0.83 2.20 3.011(5) 167.8 . O6 H6 Cl1 0.83 2.33 3.124(3) 159.4 . O7 H1W O5 0.840(19) 2.20(2) 3.009(6) 162(6) . O7 H1W Cl2 0.840(19) 3.04(5) 3.636(4) 130(5) . O7 H2W O3 0.859(19) 2.24(4) 2.935(4) 137(5) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.420 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.069 #===END data_Thoi07 _publ_contact_author_email scohen@ucsd.edu _journal_name_full 'Inorganic Chemistry' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(ipapdpm)Ni' _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 N4 Ni O2, C H2 Cl2' _chemical_formula_sum 'C24 H26 Cl2 N4 Ni O2' _chemical_formula_weight 532.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5116(6) _cell_length_b 15.8157(11) _cell_length_c 17.9622(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.2120(10) _cell_angle_gamma 90.00 _cell_volume 2418.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3901 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.8 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.052 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7507 _exptl_absorpt_correction_T_max 0.8948 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12149 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.02 _reflns_number_total 4719 _reflns_number_gt 3410 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v.1.00-2.1 (Bruker, 2006)' _computing_cell_refinement SAINT _computing_data_reduction 'SAINT v7.06A (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Sheldrick, 1994)' _computing_publication_material SHELXL97 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The asymmetric unit includes a disordered dichloromethane. Two locations for each chloride were found. The occupancy sum of the two orientations was set equal to unity, and the occupancy of the major orientation refined to 87.1(4) percent. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.3751P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4719 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.71238(4) 0.25411(2) 0.495827(19) 0.01637(11) Uani 1 1 d . . . O1 O 0.5973(2) 0.19841(12) 0.28650(10) 0.0221(5) Uani 1 1 d . . . O2 O 0.8915(2) 0.21116(12) 0.54821(10) 0.0195(4) Uani 1 1 d . . . N1 N 0.5380(2) 0.30280(14) 0.45719(12) 0.0168(5) Uani 1 1 d . . . N2 N 0.6772(2) 0.31199(14) 0.58197(12) 0.0174(5) Uani 1 1 d . . . N3 N 1.0242(2) 0.22169(14) 0.65695(13) 0.0184(5) Uani 1 1 d . . . H3A H 1.0368 0.2481 0.6997 0.022 Uiso 1 1 calc R . . N4 N 0.7277(2) 0.20138(14) 0.40059(12) 0.0171(5) Uani 1 1 d . . . C1 C 0.4995(3) 0.28098(18) 0.38835(15) 0.0188(6) Uani 1 1 d . . . C2 C 0.3567(3) 0.32095(18) 0.36745(16) 0.0219(7) Uani 1 1 d . . . H2 H 0.3041 0.3166 0.3209 0.026 Uiso 1 1 calc R . . C3 C 0.3099(3) 0.36715(19) 0.42802(16) 0.0226(7) Uani 1 1 d . . . H3 H 0.2171 0.4003 0.4313 0.027 Uiso 1 1 calc R . . C4 C 0.4255(3) 0.35677(17) 0.48543(15) 0.0175(6) Uani 1 1 d . . . C5 C 0.4340(3) 0.38844(17) 0.55812(15) 0.0169(6) Uani 1 1 d . . . C6 C 0.5638(3) 0.36771(18) 0.60524(15) 0.0179(6) Uani 1 1 d . . . C7 C 0.6085(3) 0.39608(18) 0.67739(15) 0.0194(6) Uani 1 1 d . . . H7 H 0.5523 0.4352 0.7073 0.023 Uiso 1 1 calc R . . C8 C 0.7484(3) 0.35667(18) 0.69645(15) 0.0199(6) Uani 1 1 d . . . H8 H 0.8063 0.3633 0.7414 0.024 Uiso 1 1 calc R . . C9 C 0.7869(3) 0.30496(18) 0.63563(15) 0.0169(6) Uani 1 1 d . . . C10 C 0.3051(3) 0.44172(18) 0.58734(15) 0.0176(6) Uani 1 1 d . . . C11 C 0.2366(3) 0.42043(18) 0.65558(15) 0.0195(6) Uani 1 1 d . . . H11 H 0.2748 0.3734 0.6831 0.023 Uiso 1 1 calc R . . C12 C 0.1127(3) 0.46830(18) 0.68285(16) 0.0193(6) Uani 1 1 d . . . H12 H 0.0653 0.4531 0.7287 0.023 Uiso 1 1 calc R . . C13 C 0.0578(3) 0.53746(18) 0.64412(16) 0.0217(7) Uani 1 1 d . . . H13 H -0.0262 0.5703 0.6635 0.026 Uiso 1 1 calc R . . C14 C 0.1258(3) 0.55903(19) 0.57657(16) 0.0228(7) Uani 1 1 d . . . H14 H 0.0881 0.6067 0.5497 0.027 Uiso 1 1 calc R . . C15 C 0.2483(3) 0.51139(18) 0.54816(16) 0.0211(7) Uani 1 1 d . . . H15 H 0.2938 0.5263 0.5018 0.025 Uiso 1 1 calc R . . C16 C 0.9084(3) 0.24392(17) 0.61316(15) 0.0158(6) Uani 1 1 d . . . C17 C 1.1343(3) 0.15365(18) 0.63671(16) 0.0216(7) Uani 1 1 d . . . H17 H 1.0737 0.1097 0.6087 0.026 Uiso 1 1 calc R . . C18 C 1.1983(4) 0.1129(2) 0.70654(17) 0.0399(9) Uani 1 1 d . . . H18A H 1.2582 0.1547 0.7352 0.060 Uiso 1 1 calc R . . H18B H 1.2671 0.0657 0.6930 0.060 Uiso 1 1 calc R . . H18C H 1.1110 0.0918 0.7367 0.060 Uiso 1 1 calc R . . C19 C 1.2636(4) 0.1859(2) 0.58593(19) 0.0366(8) Uani 1 1 d . . . H19A H 1.2167 0.2172 0.5443 0.055 Uiso 1 1 calc R . . H19B H 1.3238 0.1379 0.5666 0.055 Uiso 1 1 calc R . . H19C H 1.3336 0.2233 0.6141 0.055 Uiso 1 1 calc R . . C20 C 0.6134(3) 0.22197(18) 0.35273(16) 0.0188(6) Uani 1 1 d . . . C21 C 0.8603(3) 0.15087(18) 0.37129(16) 0.0218(7) Uani 1 1 d . . . H21 H 0.8317 0.1314 0.3200 0.026 Uiso 1 1 calc R . . C22 C 0.8925(3) 0.07280(18) 0.41905(17) 0.0260(7) Uani 1 1 d . . . H22A H 0.9290 0.0905 0.4685 0.039 Uiso 1 1 calc R . . H22B H 0.9734 0.0381 0.3953 0.039 Uiso 1 1 calc R . . H22C H 0.7957 0.0397 0.4240 0.039 Uiso 1 1 calc R . . C23 C 1.0058(3) 0.2068(2) 0.36552(18) 0.0306(8) Uani 1 1 d . . . H23A H 0.9848 0.2535 0.3310 0.046 Uiso 1 1 calc R . . H23B H 1.0942 0.1732 0.3471 0.046 Uiso 1 1 calc R . . H23C H 1.0318 0.2297 0.4147 0.046 Uiso 1 1 calc R . . C24 C 0.6700(4) 0.0454(2) 0.59677(19) 0.0391(9) Uani 0.871(4) 1 d P A 1 H24A H 0.6082 0.0938 0.5777 0.047 Uiso 0.871(4) 1 calc PR A 1 H24B H 0.7633 0.0385 0.5646 0.047 Uiso 0.871(4) 1 calc PR A 1 Cl1 Cl 0.7310(2) 0.06641(10) 0.68882(6) 0.0487(5) Uani 0.871(4) 1 d P A 1 Cl2 Cl 0.5549(2) -0.04688(8) 0.59299(7) 0.0447(4) Uani 0.871(4) 1 d P A 1 C25 C 0.6700(4) 0.0454(2) 0.59677(19) 0.0391(9) Uani 0.129(4) 1 d P A 2 H25A H 0.6050 0.0784 0.5614 0.047 Uiso 0.129(4) 1 calc PR A 2 H25B H 0.7803 0.0521 0.5806 0.047 Uiso 0.129(4) 1 calc PR A 2 Cl1A Cl 0.6552(13) 0.0960(6) 0.6821(5) 0.0447(4) Uani 0.129(4) 1 d P A 2 Cl2A Cl 0.6230(14) -0.0583(7) 0.5828(5) 0.0487(5) Uani 0.129(4) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01745(18) 0.0190(2) 0.01261(19) -0.00101(16) -0.00343(13) 0.00154(16) O1 0.0301(10) 0.0234(12) 0.0129(11) 0.0003(9) -0.0042(9) 0.0021(9) O2 0.0205(10) 0.0223(11) 0.0157(11) -0.0023(9) -0.0029(8) 0.0033(9) N1 0.0167(11) 0.0203(14) 0.0133(12) 0.0006(10) -0.0025(9) -0.0005(10) N2 0.0171(11) 0.0206(14) 0.0145(12) -0.0006(11) -0.0001(10) 0.0004(10) N3 0.0214(12) 0.0191(13) 0.0148(13) -0.0024(10) -0.0054(10) 0.0020(10) N4 0.0184(11) 0.0176(13) 0.0154(12) -0.0020(10) -0.0010(10) 0.0001(10) C1 0.0202(14) 0.0215(16) 0.0146(15) 0.0025(13) -0.0033(12) -0.0040(12) C2 0.0230(14) 0.0269(18) 0.0158(15) 0.0031(14) -0.0069(12) -0.0002(13) C3 0.0191(14) 0.0268(18) 0.0220(17) 0.0018(14) -0.0028(12) 0.0046(13) C4 0.0148(13) 0.0183(16) 0.0196(16) 0.0032(13) 0.0017(12) -0.0013(12) C5 0.0185(13) 0.0126(15) 0.0197(16) 0.0052(12) 0.0014(12) -0.0023(12) C6 0.0189(13) 0.0184(16) 0.0166(15) 0.0005(13) 0.0035(12) -0.0028(12) C7 0.0212(14) 0.0230(17) 0.0139(15) -0.0036(13) 0.0024(12) 0.0011(13) C8 0.0238(14) 0.0227(17) 0.0133(15) -0.0013(13) -0.0006(12) -0.0033(13) C9 0.0172(13) 0.0200(16) 0.0136(14) 0.0029(12) -0.0018(11) -0.0025(12) C10 0.0184(13) 0.0175(16) 0.0169(15) -0.0025(13) -0.0030(12) -0.0004(12) C11 0.0201(14) 0.0212(16) 0.0170(16) -0.0019(13) -0.0035(12) -0.0011(12) C12 0.0184(14) 0.0226(17) 0.0169(15) -0.0032(13) -0.0005(12) -0.0037(12) C13 0.0175(14) 0.0218(17) 0.0259(17) -0.0035(14) -0.0010(12) 0.0021(12) C14 0.0234(15) 0.0185(16) 0.0265(17) 0.0051(14) -0.0047(13) 0.0022(13) C15 0.0220(14) 0.0230(17) 0.0184(16) 0.0010(13) 0.0008(12) -0.0034(13) C16 0.0200(13) 0.0155(15) 0.0119(14) 0.0038(13) -0.0009(11) -0.0043(12) C17 0.0234(14) 0.0203(17) 0.0212(16) 0.0014(13) -0.0046(12) 0.0023(13) C18 0.053(2) 0.038(2) 0.0287(19) 0.0034(17) -0.0121(17) 0.0207(18) C19 0.0318(17) 0.032(2) 0.046(2) 0.0004(17) 0.0067(16) 0.0046(15) C20 0.0235(14) 0.0190(16) 0.0140(15) 0.0030(12) -0.0018(12) -0.0045(12) C21 0.0242(14) 0.0243(17) 0.0168(16) -0.0056(13) -0.0031(12) 0.0031(13) C22 0.0286(16) 0.0199(17) 0.0296(18) -0.0024(14) -0.0008(14) 0.0034(14) C23 0.0301(16) 0.033(2) 0.0281(18) -0.0007(16) 0.0052(14) 0.0032(15) C24 0.0376(19) 0.045(2) 0.035(2) 0.0068(18) -0.0061(16) -0.0092(17) Cl1 0.0588(10) 0.0538(9) 0.0335(6) -0.0001(6) 0.0023(6) -0.0208(8) Cl2 0.0504(8) 0.0391(7) 0.0445(7) 0.0036(5) -0.0008(6) -0.0167(6) C25 0.0376(19) 0.045(2) 0.035(2) 0.0068(18) -0.0061(16) -0.0092(17) Cl1A 0.0504(8) 0.0391(7) 0.0445(7) 0.0036(5) -0.0008(6) -0.0167(6) Cl2A 0.0588(10) 0.0538(9) 0.0335(6) -0.0001(6) 0.0023(6) -0.0208(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.808(2) . ? Ni1 N2 1.824(2) . ? Ni1 N4 1.908(2) . ? Ni1 O2 1.9132(18) . ? O1 C20 1.254(3) . ? O2 C16 1.284(3) . ? N1 C1 1.324(3) . ? N1 C4 1.381(3) . ? N2 C9 1.344(3) . ? N2 C6 1.373(3) . ? N3 C16 1.307(3) . ? N3 C17 1.473(3) . ? N3 H3A 0.8800 . ? N4 C20 1.336(3) . ? N4 C21 1.481(3) . ? C1 C2 1.419(4) . ? C1 C20 1.492(4) . ? C2 C3 1.371(4) . ? C2 H2 0.9500 . ? C3 C4 1.432(4) . ? C3 H3 0.9500 . ? C4 C5 1.400(4) . ? C5 C6 1.427(4) . ? C5 C10 1.481(4) . ? C6 C7 1.422(4) . ? C7 C8 1.386(4) . ? C7 H7 0.9500 . ? C8 C9 1.404(4) . ? C8 H8 0.9500 . ? C9 C16 1.472(4) . ? C10 C15 1.393(4) . ? C10 C11 1.400(4) . ? C11 C12 1.389(4) . ? C11 H11 0.9500 . ? C12 C13 1.377(4) . ? C12 H12 0.9500 . ? C13 C14 1.389(4) . ? C13 H13 0.9500 . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C17 C18 1.510(4) . ? C17 C19 1.520(4) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C23 1.526(4) . ? C21 C22 1.528(4) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 Cl2 1.759(3) . ? C24 Cl1 1.763(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N2 88.54(10) . . ? N1 Ni1 N4 84.31(10) . . ? N2 Ni1 N4 172.82(9) . . ? N1 Ni1 O2 172.46(9) . . ? N2 Ni1 O2 83.92(9) . . ? N4 Ni1 O2 103.22(9) . . ? C16 O2 Ni1 112.96(16) . . ? C1 N1 C4 109.5(2) . . ? C1 N1 Ni1 116.60(19) . . ? C4 N1 Ni1 133.77(19) . . ? C9 N2 C6 108.8(2) . . ? C9 N2 Ni1 116.80(18) . . ? C6 N2 Ni1 134.30(19) . . ? C16 N3 C17 121.8(2) . . ? C16 N3 H3A 119.1 . . ? C17 N3 H3A 119.1 . . ? C20 N4 C21 117.2(2) . . ? C20 N4 Ni1 114.72(18) . . ? C21 N4 Ni1 127.54(17) . . ? N1 C1 C2 109.9(2) . . ? N1 C1 C20 113.8(2) . . ? C2 C1 C20 136.3(3) . . ? C3 C2 C1 106.2(2) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? C2 C3 C4 108.0(2) . . ? C2 C3 H3 126.0 . . ? C4 C3 H3 126.0 . . ? N1 C4 C5 122.0(2) . . ? N1 C4 C3 106.4(2) . . ? C5 C4 C3 131.6(3) . . ? C4 C5 C6 120.6(2) . . ? C4 C5 C10 119.9(2) . . ? C6 C5 C10 119.5(2) . . ? N2 C6 C7 107.1(2) . . ? N2 C6 C5 120.7(2) . . ? C7 C6 C5 132.2(3) . . ? C8 C7 C6 108.1(2) . . ? C8 C7 H7 126.0 . . ? C6 C7 H7 126.0 . . ? C7 C8 C9 105.8(2) . . ? C7 C8 H8 127.1 . . ? C9 C8 H8 127.1 . . ? N2 C9 C8 110.3(2) . . ? N2 C9 C16 110.2(2) . . ? C8 C9 C16 139.6(3) . . ? C15 C10 C11 119.2(3) . . ? C15 C10 C5 121.8(2) . . ? C11 C10 C5 119.0(3) . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.6(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 120.3(3) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? O2 C16 N3 121.3(2) . . ? O2 C16 C9 115.9(2) . . ? N3 C16 C9 122.7(2) . . ? N3 C17 C18 109.6(2) . . ? N3 C17 C19 111.4(2) . . ? C18 C17 C19 112.5(3) . . ? N3 C17 H17 107.7 . . ? C18 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 N4 128.0(3) . . ? O1 C20 C1 121.6(2) . . ? N4 C20 C1 110.5(2) . . ? N4 C21 C23 109.3(2) . . ? N4 C21 C22 111.8(2) . . ? C23 C21 C22 111.3(2) . . ? N4 C21 H21 108.1 . . ? C23 C21 H21 108.1 . . ? C22 C21 H21 108.1 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Cl2 C24 Cl1 110.78(19) . . ? Cl2 C24 H24A 109.5 . . ? Cl1 C24 H24A 109.5 . . ? Cl2 C24 H24B 109.5 . . ? Cl1 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ni1 O2 C16 -3.53(18) . . . . ? N4 Ni1 O2 C16 175.70(18) . . . . ? N2 Ni1 N1 C1 -179.0(2) . . . . ? N4 Ni1 N1 C1 1.7(2) . . . . ? N2 Ni1 N1 C4 -3.2(3) . . . . ? N4 Ni1 N1 C4 177.5(3) . . . . ? N1 Ni1 N2 C9 -175.0(2) . . . . ? O2 Ni1 N2 C9 4.74(19) . . . . ? N1 Ni1 N2 C6 0.5(3) . . . . ? O2 Ni1 N2 C6 -179.7(3) . . . . ? N1 Ni1 N4 C20 -0.16(19) . . . . ? O2 Ni1 N4 C20 -179.84(19) . . . . ? N1 Ni1 N4 C21 170.9(2) . . . . ? O2 Ni1 N4 C21 -8.8(2) . . . . ? C4 N1 C1 C2 0.3(3) . . . . ? Ni1 N1 C1 C2 177.08(18) . . . . ? C4 N1 C1 C20 -179.6(2) . . . . ? Ni1 N1 C1 C20 -2.9(3) . . . . ? N1 C1 C2 C3 -0.9(3) . . . . ? C20 C1 C2 C3 179.0(3) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C1 N1 C4 C5 178.4(2) . . . . ? Ni1 N1 C4 C5 2.4(4) . . . . ? C1 N1 C4 C3 0.3(3) . . . . ? Ni1 N1 C4 C3 -175.6(2) . . . . ? C2 C3 C4 N1 -0.9(3) . . . . ? C2 C3 C4 C5 -178.7(3) . . . . ? N1 C4 C5 C6 2.0(4) . . . . ? C3 C4 C5 C6 179.5(3) . . . . ? N1 C4 C5 C10 -176.1(2) . . . . ? C3 C4 C5 C10 1.4(5) . . . . ? C9 N2 C6 C7 0.1(3) . . . . ? Ni1 N2 C6 C7 -175.7(2) . . . . ? C9 N2 C6 C5 178.7(2) . . . . ? Ni1 N2 C6 C5 2.9(4) . . . . ? C4 C5 C6 N2 -4.3(4) . . . . ? C10 C5 C6 N2 173.8(2) . . . . ? C4 C5 C6 C7 173.8(3) . . . . ? C10 C5 C6 C7 -8.1(5) . . . . ? N2 C6 C7 C8 -0.1(3) . . . . ? C5 C6 C7 C8 -178.4(3) . . . . ? C6 C7 C8 C9 0.1(3) . . . . ? C6 N2 C9 C8 -0.1(3) . . . . ? Ni1 N2 C9 C8 176.52(18) . . . . ? C6 N2 C9 C16 178.6(2) . . . . ? Ni1 N2 C9 C16 -4.8(3) . . . . ? C7 C8 C9 N2 0.0(3) . . . . ? C7 C8 C9 C16 -178.1(3) . . . . ? C4 C5 C10 C15 -50.6(4) . . . . ? C6 C5 C10 C15 131.3(3) . . . . ? C4 C5 C10 C11 128.1(3) . . . . ? C6 C5 C10 C11 -49.9(4) . . . . ? C15 C10 C11 C12 0.6(4) . . . . ? C5 C10 C11 C12 -178.2(2) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 0.8(4) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C10 -0.4(4) . . . . ? C11 C10 C15 C14 0.2(4) . . . . ? C5 C10 C15 C14 178.9(3) . . . . ? Ni1 O2 C16 N3 179.7(2) . . . . ? Ni1 O2 C16 C9 1.8(3) . . . . ? C17 N3 C16 O2 -4.7(4) . . . . ? C17 N3 C16 C9 173.1(2) . . . . ? N2 C9 C16 O2 1.8(3) . . . . ? C8 C9 C16 O2 179.9(3) . . . . ? N2 C9 C16 N3 -176.1(2) . . . . ? C8 C9 C16 N3 2.0(5) . . . . ? C16 N3 C17 C18 -152.0(3) . . . . ? C16 N3 C17 C19 82.9(3) . . . . ? C21 N4 C20 O1 6.0(4) . . . . ? Ni1 N4 C20 O1 178.1(2) . . . . ? C21 N4 C20 C1 -173.3(2) . . . . ? Ni1 N4 C20 C1 -1.2(3) . . . . ? N1 C1 C20 O1 -176.8(2) . . . . ? C2 C1 C20 O1 3.3(5) . . . . ? N1 C1 C20 N4 2.6(3) . . . . ? C2 C1 C20 N4 -177.3(3) . . . . ? C20 N4 C21 C23 107.5(3) . . . . ? Ni1 N4 C21 C23 -63.3(3) . . . . ? C20 N4 C21 C22 -128.8(3) . . . . ? Ni1 N4 C21 C22 60.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A O1 0.88 1.85 2.718(3) 170.8 4_666 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.525 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.079