data_24mayfm _publ_contact_author_name 'Prof. H. Ila' _publ_contact_author_address ;Departmet of chemistry Indian Institute of Technology - Kanpur Kanpur - 208 016 INDIA ; _publ_contact_author_email hila@iitk.ac.in _publ_contact_author_phone +915122597498 _publ_contact_author_fax +915122597436 loop_ _publ_author_name _publ_author_address 'Prof. H. Ila, ' ;Departmet of chemistry Indian Institute of Technology - Kanpur Kanpur - 208 016 INDIA ; 'Sarvesh Kumar' ;Department of Chemistry Indian Institute of Technology Kanpur 208 016 INDIA ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-(4-methoxyphenyl-1-phenylpyrazolo[3,4-b]indole) ; _chemical_name_common 'pyrazolo[3,4-b]indole' _chemical_melting_point '213-214' _chemical_formula_moiety 'C22 H17 N3 O' _chemical_formula_sum 'C22 H17 N3 O' _chemical_formula_weight 339.39 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 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.054(5) _cell_length_b 10.102(5) _cell_length_c 16.404(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 94.674(5) _cell_angle_gamma 90.000(5) _cell_volume 1660.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1878 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 26.77 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9873 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10901 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.26 _reflns_number_total 7316 _reflns_number_gt 5517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXL 5.1, XP (Sheldrick, 1994)' _computing_publication_material 'SHELXS-97' _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. ; _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^)+(0.0451P)^2^+1.0708P] 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 -2(2) _refine_ls_number_reflns 7316 _refine_ls_number_parameters 477 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1453 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.098 _refine_ls_shift/su_mean 0.052 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 O1 O -0.1732(2) 0.0093(3) 0.50358(15) 0.0206(6) Uani 1 1 d . . . N3 N -0.1011(3) 0.4359(3) 0.80035(18) 0.0183(7) Uani 1 1 d . . . O2 O 0.6773(2) 1.2202(3) 0.99178(15) 0.0196(6) Uani 1 1 d . . . N4 N 0.2662(3) 0.6627(3) 0.63883(19) 0.0183(7) Uani 1 1 d . . . N6 N 0.5943(3) 0.7889(3) 0.70077(18) 0.0166(6) Uani 1 1 d . . . N1 N 0.2301(3) 0.5437(3) 0.86934(18) 0.0171(7) Uani 1 1 d . . . N2 N -0.0214(3) 0.5143(3) 0.85365(17) 0.0159(7) Uani 1 1 d . . . N5 N 0.5161(3) 0.7038(3) 0.65029(17) 0.0157(7) Uani 1 1 d . . . C3 C 0.4714(4) 0.3340(4) 0.7220(2) 0.0233(9) Uani 1 1 d . . . H3 H 0.5228 0.2839 0.6888 0.028 Uiso 1 1 calc R . . C13 C -0.1356(4) 0.0912(4) 0.5691(2) 0.0160(8) Uani 1 1 d . . . C10 C -0.0639(3) 0.2725(4) 0.6938(2) 0.0169(8) Uani 1 1 d . . . C23 C 0.2370(3) 0.8113(4) 0.7430(2) 0.0170(8) Uani 1 1 d . . . C1 C 0.2581(4) 0.3905(4) 0.7675(2) 0.0169(8) Uani 1 1 d . . . C39 C 0.5725(3) 0.6352(4) 0.5858(2) 0.0166(8) Uani 1 1 d . . . C9 C -0.0169(3) 0.3684(4) 0.7567(2) 0.0150(8) Uani 1 1 d . . . C7 C 0.1091(3) 0.4936(4) 0.8419(2) 0.0158(8) Uani 1 1 d . . . C20 C -0.1987(4) 0.7193(4) 1.0386(2) 0.0220(8) Uani 1 1 d . . . H20 H -0.2401 0.7616 1.0801 0.026 Uiso 1 1 calc R . . C27 C 0.0350(4) 0.7040(4) 0.6798(2) 0.0206(8) Uani 1 1 d . . . H27 H -0.0061 0.6460 0.6416 0.025 Uiso 1 1 calc R . . C5 C 0.4611(3) 0.5022(4) 0.8264(2) 0.0192(8) Uani 1 1 d . . . H5 H 0.5025 0.5648 0.8615 0.023 Uiso 1 1 calc R . . C28 C 0.1720(4) 0.7239(4) 0.6856(2) 0.0175(8) Uani 1 1 d . . . C33 C 0.4966(3) 0.9566(4) 0.8823(2) 0.0178(7) Uani 1 1 d . . . H33 H 0.4256 0.9007 0.8910 0.021 Uiso 1 1 calc R . . C8 C 0.1179(3) 0.4013(3) 0.7807(2) 0.0144(7) Uani 1 1 d . . . C36 C 0.7063(3) 1.1254(4) 0.8571(2) 0.0182(7) Uani 1 1 d . . . H36 H 0.7760 1.1829 0.8482 0.022 Uiso 1 1 calc R . . C35 C 0.6427(4) 1.1329(4) 0.9288(2) 0.0175(8) Uani 1 1 d . . . C37 C 0.6653(3) 1.0310(4) 0.7985(2) 0.0193(8) Uani 1 1 d . . . H37 H 0.7093 1.0247 0.7509 0.023 Uiso 1 1 calc R . . C40 C 0.5051(3) 0.5293(4) 0.5482(2) 0.0206(8) Uani 1 1 d . . . H40 H 0.4266 0.4985 0.5678 0.025 Uiso 1 1 calc R . . C12 C -0.0222(3) 0.0688(4) 0.6214(2) 0.0165(7) Uani 1 1 d . . . H12 H 0.0300 -0.0060 0.6156 0.020 Uiso 1 1 calc R . . C30 C 0.3778(3) 0.8021(4) 0.7309(2) 0.0164(8) Uani 1 1 d . . . C44 C 0.6925(3) 0.6775(3) 0.5590(2) 0.0192(8) Uani 1 1 d . . . H44 H 0.7391 0.7472 0.5850 0.023 Uiso 1 1 calc R . . C32 C 0.5592(4) 0.9458(4) 0.8099(2) 0.0179(8) Uani 1 1 d . . . C22 C -0.2003(3) 0.6508(4) 0.8974(2) 0.0189(7) Uani 1 1 d . . . H22 H -0.2416 0.6490 0.8446 0.023 Uiso 1 1 calc R . . C17 C -0.0787(3) 0.5876(4) 0.9157(2) 0.0161(8) Uani 1 1 d . . . C29 C 0.3878(3) 0.7130(4) 0.6685(2) 0.0161(7) Uani 1 1 d . . . C26 C -0.0378(4) 0.7743(4) 0.7332(2) 0.0213(8) Uani 1 1 d . . . H26 H -0.1298 0.7628 0.7310 0.026 Uiso 1 1 calc R . . C34 C 0.5375(3) 1.0485(4) 0.9416(2) 0.0187(8) Uani 1 1 d . . . H34 H 0.4949 1.0537 0.9897 0.022 Uiso 1 1 calc R . . C6 C 0.3236(4) 0.4805(4) 0.8230(2) 0.0174(8) Uani 1 1 d . . . C31 C 0.5111(4) 0.8481(4) 0.7487(2) 0.0171(8) Uani 1 1 d . . . C18 C -0.0164(4) 0.5902(4) 0.9939(2) 0.0217(8) Uani 1 1 d . . . H18 H 0.0646 0.5469 1.0054 0.026 Uiso 1 1 calc R . . C24 C 0.1590(4) 0.8815(4) 0.7959(2) 0.0191(8) Uani 1 1 d . . . H24 H 0.1985 0.9404 0.8341 0.023 Uiso 1 1 calc R . . C11 C 0.0115(3) 0.1603(3) 0.6825(2) 0.0158(7) Uani 1 1 d . . . H11 H 0.0878 0.1459 0.7173 0.019 Uiso 1 1 calc R . . C21 C -0.2590(3) 0.7171(4) 0.9598(2) 0.0210(8) Uani 1 1 d . . . H21 H -0.3399 0.7604 0.9483 0.025 Uiso 1 1 calc R . . C4 C 0.5333(4) 0.4261(4) 0.7751(2) 0.0216(8) Uani 1 1 d . . . H4 H 0.6253 0.4371 0.7764 0.026 Uiso 1 1 calc R . . C38 C 0.7525(4) 1.3345(4) 0.9706(2) 0.0216(8) Uani 1 1 d . . . H38A H 0.7719 1.3883 1.0184 0.032 Uiso 1 1 calc R . . H38B H 0.7014 1.3849 0.9296 0.032 Uiso 1 1 calc R . . H38C H 0.8346 1.3065 0.9499 0.032 Uiso 1 1 calc R . . C2 C 0.3351(4) 0.3152(4) 0.7172(2) 0.0201(8) Uani 1 1 d . . . H2 H 0.2949 0.2533 0.6811 0.024 Uiso 1 1 calc R . . C42 C 0.6734(4) 0.5111(4) 0.4538(2) 0.0264(9) Uani 1 1 d . . . H42 H 0.7070 0.4697 0.4092 0.032 Uiso 1 1 calc R . . C14 C -0.2156(3) 0.2003(4) 0.5802(2) 0.0199(8) Uani 1 1 d . . . H14 H -0.2928 0.2133 0.5459 0.024 Uiso 1 1 calc R . . C19 C -0.0757(4) 0.6579(4) 1.0554(2) 0.0234(8) Uani 1 1 d . . . H19 H -0.0330 0.6620 1.1078 0.028 Uiso 1 1 calc R . . C15 C -0.1809(3) 0.2902(4) 0.6422(2) 0.0173(7) Uani 1 1 d . . . H15 H -0.2357 0.3626 0.6498 0.021 Uiso 1 1 calc R . . C25 C 0.0230(4) 0.8615(4) 0.7901(2) 0.0197(8) Uani 1 1 d . . . H25 H -0.0292 0.9073 0.8249 0.024 Uiso 1 1 calc R . . C43 C 0.7422(4) 0.6148(4) 0.4928(2) 0.0233(8) Uani 1 1 d . . . H43 H 0.8226 0.6427 0.4744 0.028 Uiso 1 1 calc R . . C16 C -0.0774(4) -0.0854(4) 0.4803(2) 0.0241(8) Uani 1 1 d . . . H16A H -0.1149 -0.1355 0.4342 0.036 Uiso 1 1 calc R . . H16B H -0.0544 -0.1442 0.5253 0.036 Uiso 1 1 calc R . . H16C H 0.0012 -0.0402 0.4658 0.036 Uiso 1 1 calc R . . C41 C 0.5554(4) 0.4697(4) 0.4814(2) 0.0255(9) Uani 1 1 d . . . H41 H 0.5085 0.4007 0.4548 0.031 Uiso 1 1 calc R . . H1N1 H 0.250(3) 0.615(4) 0.907(2) 0.018(9) Uiso 1 1 d . . . H2N H 0.250(5) 0.605(5) 0.588(3) 0.070(17) Uiso 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 O1 0.0222(14) 0.0221(15) 0.0172(13) -0.0036(11) -0.0003(10) 0.0032(11) N3 0.0162(16) 0.0223(17) 0.0166(15) 0.0005(14) 0.0034(12) -0.0040(13) O2 0.0215(14) 0.0189(14) 0.0187(13) -0.0018(11) 0.0044(10) -0.0062(11) N4 0.0101(14) 0.0238(18) 0.0213(16) -0.0014(14) 0.0033(12) -0.0046(13) N6 0.0114(14) 0.0193(17) 0.0191(15) -0.0062(13) 0.0012(12) 0.0001(13) N1 0.0159(15) 0.0194(17) 0.0162(15) -0.0027(13) 0.0019(12) 0.0003(13) N2 0.0152(15) 0.0166(16) 0.0158(15) -0.0031(13) 0.0015(12) -0.0014(13) N5 0.0135(15) 0.0172(17) 0.0165(15) -0.0011(13) 0.0022(12) 0.0016(13) C3 0.019(2) 0.032(2) 0.0196(19) -0.0007(17) 0.0055(15) 0.0026(17) C13 0.0217(19) 0.0165(19) 0.0107(16) -0.0002(14) 0.0055(13) -0.0024(16) C10 0.0140(18) 0.020(2) 0.0171(18) 0.0033(15) 0.0057(14) -0.0019(15) C23 0.0157(18) 0.017(2) 0.0182(18) 0.0015(15) 0.0022(14) -0.0039(15) C1 0.0166(18) 0.0179(19) 0.0162(17) 0.0031(15) 0.0024(13) 0.0020(15) C39 0.0145(17) 0.022(2) 0.0133(17) 0.0000(15) 0.0017(13) 0.0009(15) C9 0.0136(18) 0.019(2) 0.0127(17) 0.0017(15) 0.0015(13) -0.0039(15) C7 0.0128(17) 0.018(2) 0.0171(17) 0.0045(14) 0.0034(13) 0.0003(15) C20 0.0227(19) 0.023(2) 0.0213(19) -0.0081(17) 0.0085(15) -0.0005(17) C27 0.0192(19) 0.021(2) 0.0218(19) 0.0054(16) 0.0003(15) 0.0018(16) C5 0.0155(18) 0.025(2) 0.0177(18) -0.0003(16) 0.0037(14) -0.0033(16) C28 0.0193(18) 0.020(2) 0.0137(17) 0.0011(16) 0.0051(14) 0.0027(16) C33 0.0139(17) 0.024(2) 0.0159(17) -0.0025(15) 0.0025(13) -0.0045(15) C8 0.0170(17) 0.0140(18) 0.0124(16) -0.0015(14) 0.0025(13) 0.0027(14) C36 0.0127(16) 0.0197(19) 0.0222(18) -0.0033(15) 0.0022(13) -0.0048(14) C35 0.0189(18) 0.017(2) 0.0158(17) -0.0054(15) -0.0029(14) 0.0019(15) C37 0.0193(18) 0.0210(19) 0.0184(18) -0.0004(15) 0.0068(14) -0.0010(15) C40 0.0116(16) 0.024(2) 0.0263(19) -0.0006(16) 0.0040(14) -0.0018(15) C12 0.0141(17) 0.0195(19) 0.0168(17) 0.0035(15) 0.0075(13) 0.0009(14) C30 0.0122(17) 0.021(2) 0.0162(17) 0.0005(15) 0.0028(13) 0.0011(15) C44 0.0181(18) 0.020(2) 0.0203(18) -0.0038(15) 0.0044(14) -0.0027(15) C32 0.0172(18) 0.019(2) 0.0176(18) -0.0009(16) 0.0020(14) 0.0029(16) C22 0.0123(16) 0.0208(19) 0.0242(18) -0.0005(16) 0.0052(14) -0.0036(15) C17 0.0118(17) 0.0176(19) 0.0191(18) 0.0009(15) 0.0019(14) -0.0027(15) C29 0.0156(17) 0.0183(19) 0.0151(17) 0.0041(15) 0.0054(14) -0.0021(15) C26 0.0155(19) 0.027(2) 0.0223(19) 0.0065(17) 0.0038(15) -0.0023(16) C34 0.0172(18) 0.026(2) 0.0137(17) -0.0046(15) 0.0040(13) -0.0005(15) C6 0.0146(18) 0.020(2) 0.0177(18) 0.0061(15) 0.0031(14) 0.0008(15) C31 0.0164(18) 0.020(2) 0.0150(18) 0.0007(15) 0.0019(14) 0.0006(15) C18 0.0181(18) 0.024(2) 0.0235(19) 0.0018(16) 0.0034(14) 0.0001(15) C24 0.0162(18) 0.022(2) 0.0188(18) 0.0001(16) 0.0018(14) 0.0029(15) C11 0.0139(16) 0.0205(19) 0.0131(17) 0.0011(14) 0.0014(13) -0.0038(14) C21 0.0128(17) 0.0182(19) 0.033(2) -0.0015(17) 0.0085(15) -0.0007(15) C4 0.0144(18) 0.029(2) 0.0223(19) 0.0038(17) 0.0039(15) 0.0015(16) C38 0.0207(19) 0.019(2) 0.0254(19) -0.0023(16) 0.0032(15) -0.0029(15) C2 0.0162(18) 0.025(2) 0.0203(18) 0.0016(16) 0.0061(14) 0.0021(15) C42 0.023(2) 0.031(2) 0.026(2) -0.0082(18) 0.0089(16) 0.0006(18) C14 0.0127(17) 0.029(2) 0.0183(18) 0.0005(16) 0.0002(13) -0.0001(15) C19 0.0236(19) 0.028(2) 0.0187(19) -0.0031(16) 0.0024(15) -0.0077(17) C15 0.0162(17) 0.0200(19) 0.0167(17) -0.0034(15) 0.0077(13) 0.0016(15) C25 0.0186(19) 0.022(2) 0.0186(18) 0.0028(16) 0.0047(14) 0.0055(16) C43 0.0186(18) 0.024(2) 0.027(2) -0.0051(17) 0.0048(15) -0.0021(16) C16 0.027(2) 0.021(2) 0.0239(19) -0.0074(16) 0.0031(16) 0.0025(16) C41 0.023(2) 0.022(2) 0.031(2) -0.0087(17) 0.0017(16) -0.0034(16) _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 O1 C13 1.384(4) . ? O1 C16 1.432(4) . ? N3 C9 1.339(4) . ? N3 N2 1.385(4) . ? O2 C35 1.382(4) . ? O2 C38 1.438(4) . ? N4 C29 1.375(5) . ? N4 C28 1.409(4) . ? N6 C31 1.335(4) . ? N6 N5 1.391(4) . ? N1 C7 1.360(5) . ? N1 C6 1.409(5) . ? N2 C7 1.358(4) . ? N2 C17 1.419(4) . ? N5 C29 1.351(4) . ? N5 C39 1.421(4) . ? C3 C2 1.379(5) . ? C3 C4 1.388(6) . ? C13 C14 1.385(5) . ? C13 C12 1.389(5) . ? C10 C11 1.384(5) . ? C10 C15 1.403(5) . ? C10 C9 1.466(5) . ? C23 C24 1.407(5) . ? C23 C28 1.412(5) . ? C23 C30 1.449(5) . ? C1 C2 1.401(5) . ? C1 C6 1.412(5) . ? C1 C8 1.448(5) . ? C39 C40 1.383(5) . ? C39 C44 1.385(5) . ? C9 C8 1.420(5) . ? C7 C8 1.378(5) . ? C20 C21 1.381(5) . ? C20 C19 1.391(5) . ? C27 C26 1.383(5) . ? C27 C28 1.387(5) . ? C5 C4 1.387(5) . ? C5 C6 1.396(5) . ? C33 C34 1.383(5) . ? C33 C32 1.393(5) . ? C36 C35 1.386(5) . ? C36 C37 1.392(5) . ? C35 C34 1.387(5) . ? C37 C32 1.395(5) . ? C40 C41 1.382(5) . ? C12 C11 1.384(5) . ? C30 C29 1.373(5) . ? C30 C31 1.425(5) . ? C44 C43 1.384(5) . ? C32 C31 1.462(5) . ? C22 C17 1.390(5) . ? C22 C21 1.394(5) . ? C17 C18 1.380(5) . ? C26 C25 1.388(5) . ? C18 C19 1.392(5) . ? C24 C25 1.378(5) . ? C42 C41 1.369(5) . ? C42 C43 1.383(5) . ? C14 C15 1.387(5) . ? 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 C13 O1 C16 117.3(3) . . ? C9 N3 N2 105.7(3) . . ? C35 O2 C38 115.9(3) . . ? C29 N4 C28 105.2(3) . . ? C31 N6 N5 106.0(3) . . ? C7 N1 C6 105.7(3) . . ? C7 N2 N3 109.7(3) . . ? C7 N2 C17 129.5(3) . . ? N3 N2 C17 120.2(3) . . ? C29 N5 N6 109.2(3) . . ? C29 N5 C39 130.1(3) . . ? N6 N5 C39 120.3(3) . . ? C2 C3 C4 121.4(4) . . ? O1 C13 C14 116.9(3) . . ? O1 C13 C12 122.8(3) . . ? C14 C13 C12 120.3(3) . . ? C11 C10 C15 117.7(3) . . ? C11 C10 C9 119.1(3) . . ? C15 C10 C9 123.1(3) . . ? C24 C23 C28 118.4(3) . . ? C24 C23 C30 135.8(3) . . ? C28 C23 C30 105.8(3) . . ? C2 C1 C6 118.6(3) . . ? C2 C1 C8 136.1(4) . . ? C6 C1 C8 105.3(3) . . ? C40 C39 C44 120.3(3) . . ? C40 C39 N5 119.9(3) . . ? C44 C39 N5 119.8(3) . . ? N3 C9 C8 111.3(3) . . ? N3 C9 C10 122.1(3) . . ? C8 C9 C10 126.6(3) . . ? N2 C7 N1 138.1(3) . . ? N2 C7 C8 109.1(3) . . ? N1 C7 C8 112.6(3) . . ? C21 C20 C19 119.5(3) . . ? C26 C27 C28 117.1(4) . . ? C4 C5 C6 117.0(4) . . ? C27 C28 C23 122.7(3) . . ? C27 C28 N4 127.3(3) . . ? C23 C28 N4 110.0(3) . . ? C34 C33 C32 121.5(3) . . ? C7 C8 C9 104.1(3) . . ? C7 C8 C1 106.3(3) . . ? C9 C8 C1 149.3(3) . . ? C35 C36 C37 119.5(3) . . ? O2 C35 C36 124.3(3) . . ? O2 C35 C34 115.3(3) . . ? C36 C35 C34 120.3(3) . . ? C36 C37 C32 121.1(3) . . ? C41 C40 C39 119.5(3) . . ? C11 C12 C13 118.6(3) . . ? C29 C30 C31 104.0(3) . . ? C29 C30 C23 106.0(3) . . ? C31 C30 C23 149.8(3) . . ? C43 C44 C39 119.1(3) . . ? C33 C32 C37 118.0(3) . . ? C33 C32 C31 119.4(3) . . ? C37 C32 C31 122.5(3) . . ? C17 C22 C21 118.6(3) . . ? C18 C17 C22 121.1(3) . . ? C18 C17 N2 119.8(3) . . ? C22 C17 N2 119.1(3) . . ? N5 C29 C30 109.8(3) . . ? N5 C29 N4 137.2(3) . . ? C30 C29 N4 112.9(3) . . ? C25 C26 C27 121.7(3) . . ? C33 C34 C35 119.5(3) . . ? C5 C6 N1 127.6(3) . . ? C5 C6 C1 122.3(3) . . ? N1 C6 C1 110.1(3) . . ? N6 C31 C30 110.9(3) . . ? N6 C31 C32 121.3(3) . . ? C30 C31 C32 127.8(3) . . ? C17 C18 C19 119.6(4) . . ? C25 C24 C23 118.9(3) . . ? C10 C11 C12 122.6(3) . . ? C20 C21 C22 121.0(3) . . ? C5 C4 C3 121.5(4) . . ? C3 C2 C1 119.1(4) . . ? C41 C42 C43 119.5(4) . . ? C15 C14 C13 120.2(3) . . ? C20 C19 C18 120.1(3) . . ? C14 C15 C10 120.4(3) . . ? C24 C25 C26 121.3(3) . . ? C42 C43 C44 120.7(3) . . ? C42 C41 C40 120.8(4) . . ? 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 C9 N3 N2 C7 -0.1(4) . . . . ? C9 N3 N2 C17 -172.6(3) . . . . ? C31 N6 N5 C29 0.0(4) . . . . ? C31 N6 N5 C39 173.6(3) . . . . ? C16 O1 C13 C14 166.4(3) . . . . ? C16 O1 C13 C12 -12.6(5) . . . . ? C29 N5 C39 C40 -22.8(6) . . . . ? N6 N5 C39 C40 165.1(3) . . . . ? C29 N5 C39 C44 154.9(4) . . . . ? N6 N5 C39 C44 -17.2(5) . . . . ? N2 N3 C9 C8 0.1(4) . . . . ? N2 N3 C9 C10 179.2(3) . . . . ? C11 C10 C9 N3 -145.0(3) . . . . ? C15 C10 C9 N3 36.7(5) . . . . ? C11 C10 C9 C8 33.9(5) . . . . ? C15 C10 C9 C8 -144.4(4) . . . . ? N3 N2 C7 N1 174.6(4) . . . . ? C17 N2 C7 N1 -13.9(7) . . . . ? N3 N2 C7 C8 0.1(4) . . . . ? C17 N2 C7 C8 171.6(3) . . . . ? C6 N1 C7 N2 -174.2(4) . . . . ? C6 N1 C7 C8 0.2(4) . . . . ? C26 C27 C28 C23 0.0(5) . . . . ? C26 C27 C28 N4 179.1(3) . . . . ? C24 C23 C28 C27 -0.4(5) . . . . ? C30 C23 C28 C27 178.8(3) . . . . ? C24 C23 C28 N4 -179.7(3) . . . . ? C30 C23 C28 N4 -0.5(4) . . . . ? C29 N4 C28 C27 -178.9(4) . . . . ? C29 N4 C28 C23 0.3(4) . . . . ? N2 C7 C8 C9 0.0(4) . . . . ? N1 C7 C8 C9 -176.0(3) . . . . ? N2 C7 C8 C1 176.2(3) . . . . ? N1 C7 C8 C1 0.2(4) . . . . ? N3 C9 C8 C7 -0.1(4) . . . . ? C10 C9 C8 C7 -179.1(3) . . . . ? N3 C9 C8 C1 -172.9(5) . . . . ? C10 C9 C8 C1 8.0(9) . . . . ? C2 C1 C8 C7 178.2(4) . . . . ? C6 C1 C8 C7 -0.5(4) . . . . ? C2 C1 C8 C9 -9.0(9) . . . . ? C6 C1 C8 C9 172.3(6) . . . . ? C38 O2 C35 C36 20.4(5) . . . . ? C38 O2 C35 C34 -160.3(3) . . . . ? C37 C36 C35 O2 178.3(3) . . . . ? C37 C36 C35 C34 -0.9(5) . . . . ? C35 C36 C37 C32 1.4(5) . . . . ? C44 C39 C40 C41 -2.8(5) . . . . ? N5 C39 C40 C41 174.9(3) . . . . ? O1 C13 C12 C11 176.4(3) . . . . ? C14 C13 C12 C11 -2.5(5) . . . . ? C24 C23 C30 C29 179.4(4) . . . . ? C28 C23 C30 C29 0.4(4) . . . . ? C24 C23 C30 C31 -8.3(10) . . . . ? C28 C23 C30 C31 172.7(6) . . . . ? C40 C39 C44 C43 1.7(5) . . . . ? N5 C39 C44 C43 -176.1(3) . . . . ? C34 C33 C32 C37 -0.1(5) . . . . ? C34 C33 C32 C31 -179.3(3) . . . . ? C36 C37 C32 C33 -0.9(5) . . . . ? C36 C37 C32 C31 178.3(3) . . . . ? C21 C22 C17 C18 -0.2(5) . . . . ? C21 C22 C17 N2 176.9(3) . . . . ? C7 N2 C17 C18 -34.5(6) . . . . ? N3 N2 C17 C18 136.3(4) . . . . ? C7 N2 C17 C22 148.3(4) . . . . ? N3 N2 C17 C22 -40.9(5) . . . . ? N6 N5 C29 C30 -0.5(4) . . . . ? C39 N5 C29 C30 -173.2(3) . . . . ? N6 N5 C29 N4 175.5(4) . . . . ? C39 N5 C29 N4 2.7(7) . . . . ? C31 C30 C29 N5 0.8(4) . . . . ? C23 C30 C29 N5 176.8(3) . . . . ? C31 C30 C29 N4 -176.2(3) . . . . ? C23 C30 C29 N4 -0.3(4) . . . . ? C28 N4 C29 N5 -175.9(4) . . . . ? C28 N4 C29 C30 0.0(4) . . . . ? C28 C27 C26 C25 0.3(5) . . . . ? C32 C33 C34 C35 0.5(5) . . . . ? O2 C35 C34 C33 -179.3(3) . . . . ? C36 C35 C34 C33 0.0(5) . . . . ? C4 C5 C6 N1 179.2(3) . . . . ? C4 C5 C6 C1 -3.1(5) . . . . ? C7 N1 C6 C5 177.5(4) . . . . ? C7 N1 C6 C1 -0.5(4) . . . . ? C2 C1 C6 C5 3.5(5) . . . . ? C8 C1 C6 C5 -177.5(3) . . . . ? C2 C1 C6 N1 -178.4(3) . . . . ? C8 C1 C6 N1 0.6(4) . . . . ? N5 N6 C31 C30 0.5(4) . . . . ? N5 N6 C31 C32 -179.6(3) . . . . ? C29 C30 C31 N6 -0.8(4) . . . . ? C23 C30 C31 N6 -173.1(6) . . . . ? C29 C30 C31 C32 179.4(4) . . . . ? C23 C30 C31 C32 7.1(9) . . . . ? C33 C32 C31 N6 -147.9(4) . . . . ? C37 C32 C31 N6 33.0(6) . . . . ? C33 C32 C31 C30 31.9(6) . . . . ? C37 C32 C31 C30 -147.2(4) . . . . ? C22 C17 C18 C19 -0.4(6) . . . . ? N2 C17 C18 C19 -177.5(3) . . . . ? C28 C23 C24 C25 0.5(5) . . . . ? C30 C23 C24 C25 -178.4(4) . . . . ? C15 C10 C11 C12 2.0(5) . . . . ? C9 C10 C11 C12 -176.3(3) . . . . ? C13 C12 C11 C10 0.5(5) . . . . ? C19 C20 C21 C22 1.9(6) . . . . ? C17 C22 C21 C20 -0.5(5) . . . . ? C6 C5 C4 C3 0.9(6) . . . . ? C2 C3 C4 C5 0.8(6) . . . . ? C4 C3 C2 C1 -0.3(6) . . . . ? C6 C1 C2 C3 -1.8(5) . . . . ? C8 C1 C2 C3 179.6(4) . . . . ? O1 C13 C14 C15 -177.1(3) . . . . ? C12 C13 C14 C15 1.9(5) . . . . ? C21 C20 C19 C18 -2.5(6) . . . . ? C17 C18 C19 C20 1.8(6) . . . . ? C13 C14 C15 C10 0.7(5) . . . . ? C11 C10 C15 C14 -2.6(5) . . . . ? C9 C10 C15 C14 175.6(3) . . . . ? C23 C24 C25 C26 -0.2(5) . . . . ? C27 C26 C25 C24 -0.3(6) . . . . ? C41 C42 C43 C44 -0.4(6) . . . . ? C39 C44 C43 C42 0.0(6) . . . . ? C43 C42 C41 C40 -0.8(6) . . . . ? C39 C40 C41 C42 2.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.369 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.076