data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 165 degree C _chemical_formula_moiety 'C25 H24 N4 O4' _chemical_formula_sum 'C25 H24 N4 O4' _chemical_formula_weight 444.48 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 Triclinic _symmetry_space_group_name_H-M P -1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8590(5) _cell_length_b 10.8310(5) _cell_length_c 11.3140(5) _cell_angle_alpha 88.635(5) _cell_angle_beta 69.452(5) _cell_angle_gamma 75.314(5) _cell_volume 1091.48(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 15 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Enraf. Nonius Cad4 Mach2 _diffrn_measurement_method Theta-2Theta scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1h _diffrn_standards_decay_% <0.5% _diffrn_reflns_number 3044 _diffrn_reflns_av_R_equivalents 0.0129 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 22.49 _reflns_number_total 2841 _reflns_number_gt 1943 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 Mach2 _computing_cell_refinement CAD4 _computing_data_reduction SHELXL-97 _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1e _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0650P)^2^+0.2253P] 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 SHELXL _refine_ls_extinction_coef 0.035(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2841 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _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 O4 O 0.5647(3) 0.9268(2) 0.6926(2) 0.0882(9) Uani 1 1 d . . . O3 O 0.6435(3) 1.0298(2) 0.5291(3) 0.0791(8) Uani 1 1 d . . . O1 O 0.9277(2) 0.6187(2) 0.10234(19) 0.0635(7) Uani 1 1 d . . . O2 O 0.8258(3) 0.8209(2) 0.1139(2) 0.0870(9) Uani 1 1 d . . . N1 N 0.9308(3) 0.1761(2) 0.3060(2) 0.0493(7) Uani 1 1 d . . . N2 N 0.7084(2) 0.50139(19) 0.27282(19) 0.0352(6) Uani 1 1 d . . . N4 N 0.6212(3) 0.9316(3) 0.5787(3) 0.0580(7) Uani 1 1 d . . . N3 N 0.8381(3) 0.7177(3) 0.1597(2) 0.0509(7) Uani 1 1 d . . . C1 C 1.0863(4) 0.1287(3) 0.2957(4) 0.0774(11) Uani 1 1 d . . . H1A H 1.1082 0.1831 0.3485 0.116 Uiso 1 1 calc R . . H1B H 1.1507 0.1286 0.2094 0.116 Uiso 1 1 calc R . . H1C H 1.1029 0.0432 0.3226 0.116 Uiso 1 1 calc R . . C2 C 0.8978(4) 0.0941(3) 0.2271(4) 0.0767(11) Uani 1 1 d . . . H2A H 0.9188 0.0079 0.2516 0.115 Uiso 1 1 calc R . . H2B H 0.9589 0.0968 0.1402 0.115 Uiso 1 1 calc R . . H2C H 0.7938 0.1230 0.2368 0.115 Uiso 1 1 calc R . . C3 C 0.9008(3) 0.3071(2) 0.2737(3) 0.0422(7) Uani 1 1 d . . . H3A H 0.9500 0.3101 0.1833 0.051 Uiso 1 1 calc R . . H3B H 0.9430 0.3551 0.3165 0.051 Uiso 1 1 calc R . . C4 C 0.7349(3) 0.3695(2) 0.3099(2) 0.0383(7) Uani 1 1 d . . . H4A H 0.6918 0.3207 0.2688 0.046 Uiso 1 1 calc R . . H4B H 0.6857 0.3692 0.4007 0.046 Uiso 1 1 calc R . . C5 C 0.7139(3) 0.5981(2) 0.3430(2) 0.0334(6) Uani 1 1 d . . . C10 C 0.6746(3) 0.5950(3) 0.4753(3) 0.0444(7) Uani 1 1 d . . . H10 H 0.6685 0.5180 0.5123 0.053 Uiso 1 1 calc R . . C9 C 0.6455(3) 0.7023(3) 0.5503(3) 0.0467(8) Uani 1 1 d . . . H9 H 0.6156 0.6984 0.6377 0.056 Uiso 1 1 calc R . . C8 C 0.6600(3) 0.8166(3) 0.4979(3) 0.0417(7) Uani 1 1 d . . . C7 C 0.7140(3) 0.8219(3) 0.3695(3) 0.0427(7) Uani 1 1 d . . . H7 H 0.7278 0.8983 0.3342 0.051 Uiso 1 1 calc R . . C6 C 0.7479(3) 0.7130(2) 0.2927(2) 0.0370(7) Uani 1 1 d . . . C11 C 0.6779(3) 0.5229(2) 0.1546(2) 0.0354(6) Uani 1 1 d . . . H11A H 0.7660 0.4785 0.0842 0.042 Uiso 1 1 calc R . . H11B H 0.6587 0.6136 0.1417 0.042 Uiso 1 1 calc R . . C12 C 0.5451(3) 0.4765(2) 0.1564(2) 0.0322(6) Uani 1 1 d . . . C13 C 0.5644(3) 0.3643(2) 0.0863(2) 0.0348(6) Uani 1 1 d . . . C14 C 0.7072(3) 0.2819(3) 0.0130(3) 0.0453(7) Uani 1 1 d . . . H14 H 0.7940 0.3029 0.0104 0.054 Uiso 1 1 calc R . . C15 C 0.7195(4) 0.1746(3) -0.0524(3) 0.0581(9) Uani 1 1 d . . . H15 H 0.8143 0.1225 -0.0976 0.070 Uiso 1 1 calc R . . C16 C 0.5926(4) 0.1399(3) -0.0536(3) 0.0611(9) Uani 1 1 d . . . H16 H 0.6035 0.0666 -0.1010 0.073 Uiso 1 1 calc R . . C17 C 0.4546(4) 0.2129(3) 0.0138(3) 0.0500(8) Uani 1 1 d . . . H17 H 0.3706 0.1888 0.0137 0.060 Uiso 1 1 calc R . . C18 C 0.4354(3) 0.3267(2) 0.0855(2) 0.0388(7) Uani 1 1 d . . . C19 C 0.2937(3) 0.4015(3) 0.1553(3) 0.0444(7) Uani 1 1 d . . . H19 H 0.2101 0.3777 0.1536 0.053 Uiso 1 1 calc R . . C20 C 0.2726(3) 0.5115(2) 0.2282(2) 0.0385(7) Uani 1 1 d . . . C21 C 0.1275(3) 0.5847(3) 0.3020(3) 0.0534(8) Uani 1 1 d . . . H21 H 0.0443 0.5592 0.3021 0.064 Uiso 1 1 calc R . . C22 C 0.1075(3) 0.6908(3) 0.3723(3) 0.0600(9) Uani 1 1 d . . . H22 H 0.0108 0.7372 0.4208 0.072 Uiso 1 1 calc R . . C23 C 0.2313(3) 0.7323(3) 0.3732(3) 0.0500(8) Uani 1 1 d . . . H23 H 0.2162 0.8061 0.4216 0.060 Uiso 1 1 calc R . . C24 C 0.3720(3) 0.6648(2) 0.3037(2) 0.0390(7) Uani 1 1 d . . . H24 H 0.4529 0.6935 0.3048 0.047 Uiso 1 1 calc R . . C25 C 0.4000(3) 0.5510(2) 0.2287(2) 0.0319(6) 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 O4 0.114(2) 0.0797(18) 0.0573(17) -0.0215(13) -0.0287(15) -0.0023(15) O3 0.0892(19) 0.0516(15) 0.098(2) -0.0132(14) -0.0344(15) -0.0191(14) O1 0.0478(14) 0.0789(16) 0.0541(14) -0.0126(12) 0.0015(11) -0.0265(12) O2 0.131(2) 0.0738(17) 0.0596(16) 0.0242(13) -0.0208(15) -0.0538(16) N1 0.0406(15) 0.0385(14) 0.0596(16) 0.0069(11) -0.0147(12) 0.0005(11) N2 0.0350(13) 0.0342(12) 0.0402(13) 0.0052(10) -0.0188(10) -0.0081(10) N4 0.0530(17) 0.0565(19) 0.065(2) -0.0128(15) -0.0291(15) -0.0026(14) N3 0.0540(17) 0.0600(18) 0.0457(16) 0.0052(14) -0.0140(13) -0.0327(15) C1 0.062(2) 0.059(2) 0.104(3) -0.0023(19) -0.040(2) 0.0123(17) C2 0.070(3) 0.0391(19) 0.119(3) 0.0014(19) -0.033(2) -0.0129(17) C3 0.0319(16) 0.0388(16) 0.0525(18) 0.0041(13) -0.0131(13) -0.0065(12) C4 0.0356(16) 0.0359(15) 0.0446(17) 0.0047(12) -0.0157(13) -0.0096(12) C5 0.0210(14) 0.0367(16) 0.0429(16) 0.0021(12) -0.0145(12) -0.0038(11) C10 0.0513(19) 0.0436(17) 0.0413(17) 0.0082(13) -0.0211(14) -0.0116(14) C9 0.0468(19) 0.056(2) 0.0387(17) 0.0008(15) -0.0198(14) -0.0091(15) C8 0.0351(16) 0.0424(17) 0.0471(18) -0.0066(14) -0.0176(13) -0.0040(13) C7 0.0375(17) 0.0388(16) 0.054(2) 0.0043(14) -0.0186(14) -0.0108(13) C6 0.0308(15) 0.0441(17) 0.0384(16) 0.0044(13) -0.0127(12) -0.0134(13) C11 0.0300(15) 0.0418(16) 0.0346(15) 0.0029(12) -0.0118(12) -0.0094(12) C12 0.0324(15) 0.0369(15) 0.0309(14) 0.0059(12) -0.0142(12) -0.0117(12) C13 0.0384(16) 0.0358(15) 0.0306(14) 0.0061(12) -0.0139(12) -0.0084(12) C14 0.0409(18) 0.0468(18) 0.0445(17) -0.0005(14) -0.0141(14) -0.0064(14) C15 0.059(2) 0.0479(19) 0.055(2) -0.0103(15) -0.0164(16) 0.0017(16) C16 0.082(3) 0.0464(19) 0.055(2) -0.0067(15) -0.0253(19) -0.0161(19) C17 0.063(2) 0.0510(19) 0.0481(18) 0.0080(15) -0.0259(16) -0.0282(17) C18 0.0451(18) 0.0415(16) 0.0371(15) 0.0087(13) -0.0196(13) -0.0172(14) C19 0.0413(18) 0.0547(19) 0.0468(17) 0.0125(14) -0.0210(14) -0.0221(15) C20 0.0329(16) 0.0450(17) 0.0396(16) 0.0078(13) -0.0152(13) -0.0109(13) C21 0.0291(17) 0.066(2) 0.062(2) 0.0033(17) -0.0152(15) -0.0087(15) C22 0.0311(18) 0.072(2) 0.061(2) -0.0053(18) -0.0081(15) 0.0025(16) C23 0.048(2) 0.0464(17) 0.0487(18) -0.0027(14) -0.0169(15) -0.0003(15) C24 0.0369(17) 0.0395(16) 0.0400(16) 0.0009(13) -0.0155(13) -0.0060(13) C25 0.0303(15) 0.0365(15) 0.0298(14) 0.0058(11) -0.0133(12) -0.0069(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 O4 N4 1.217(3) . ? O3 N4 1.224(3) . ? O1 N3 1.226(3) . ? O2 N3 1.216(3) . ? N1 C3 1.440(3) . ? N1 C2 1.442(4) . ? N1 C1 1.451(4) . ? N2 C5 1.352(3) . ? N2 C4 1.464(3) . ? N2 C11 1.471(3) . ? N4 C8 1.449(4) . ? N3 C6 1.463(3) . ? C3 C4 1.511(3) . ? C5 C10 1.411(4) . ? C5 C6 1.424(3) . ? C10 C9 1.364(4) . ? C9 C8 1.378(4) . ? C8 C7 1.366(4) . ? C7 C6 1.380(4) . ? C11 C12 1.510(3) . ? C12 C13 1.402(3) . ? C12 C25 1.411(3) . ? C13 C14 1.430(4) . ? C13 C18 1.434(4) . ? C14 C15 1.349(4) . ? C15 C16 1.399(5) . ? C16 C17 1.346(4) . ? C17 C18 1.425(4) . ? C18 C19 1.383(4) . ? C19 C20 1.394(4) . ? C20 C21 1.411(4) . ? C20 C25 1.427(4) . ? C21 C22 1.346(4) . ? C22 C23 1.406(4) . ? C23 C24 1.351(4) . ? C24 C25 1.424(3) . ? 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 N1 C2 112.0(2) . . ? C3 N1 C1 110.5(2) . . ? C2 N1 C1 109.4(2) . . ? C5 N2 C4 121.5(2) . . ? C5 N2 C11 121.8(2) . . ? C4 N2 C11 116.7(2) . . ? O4 N4 O3 123.0(3) . . ? O4 N4 C8 118.5(3) . . ? O3 N4 C8 118.5(3) . . ? O2 N3 O1 123.6(3) . . ? O2 N3 C6 118.2(3) . . ? O1 N3 C6 118.1(2) . . ? N1 C3 C4 112.4(2) . . ? N2 C4 C3 111.0(2) . . ? N2 C5 C10 121.2(2) . . ? N2 C5 C6 123.7(2) . . ? C10 C5 C6 115.0(2) . . ? C9 C10 C5 121.5(3) . . ? C10 C9 C8 120.6(3) . . ? C7 C8 C9 120.3(3) . . ? C7 C8 N4 119.5(3) . . ? C9 C8 N4 120.2(3) . . ? C8 C7 C6 119.4(3) . . ? C7 C6 C5 121.8(2) . . ? C7 C6 N3 115.7(2) . . ? C5 C6 N3 122.0(2) . . ? N2 C11 C12 112.2(2) . . ? C13 C12 C25 120.6(2) . . ? C13 C12 C11 121.3(2) . . ? C25 C12 C11 118.1(2) . . ? C12 C13 C14 124.2(2) . . ? C12 C13 C18 119.7(2) . . ? C14 C13 C18 116.1(2) . . ? C15 C14 C13 121.8(3) . . ? C14 C15 C16 121.4(3) . . ? C17 C16 C15 119.9(3) . . ? C16 C17 C18 121.0(3) . . ? C19 C18 C17 121.1(3) . . ? C19 C18 C13 119.1(2) . . ? C17 C18 C13 119.8(3) . . ? C18 C19 C20 121.9(3) . . ? C19 C20 C21 121.2(3) . . ? C19 C20 C25 119.6(2) . . ? C21 C20 C25 119.2(3) . . ? C22 C21 C20 121.1(3) . . ? C21 C22 C23 120.7(3) . . ? C24 C23 C22 120.0(3) . . ? C23 C24 C25 121.8(3) . . ? C12 C25 C24 123.7(2) . . ? C12 C25 C20 119.1(2) . . ? C24 C25 C20 117.2(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 C2 N1 C3 C4 70.2(3) . . . . ? C1 N1 C3 C4 -167.5(3) . . . . ? C5 N2 C4 C3 -79.7(3) . . . . ? C11 N2 C4 C3 99.3(3) . . . . ? N1 C3 C4 N2 -178.5(2) . . . . ? C4 N2 C5 C10 -30.4(3) . . . . ? C11 N2 C5 C10 150.6(2) . . . . ? C4 N2 C5 C6 154.4(2) . . . . ? C11 N2 C5 C6 -24.6(3) . . . . ? N2 C5 C10 C9 -164.3(2) . . . . ? C6 C5 C10 C9 11.2(4) . . . . ? C5 C10 C9 C8 -2.8(4) . . . . ? C10 C9 C8 C7 -4.7(4) . . . . ? C10 C9 C8 N4 176.7(3) . . . . ? O4 N4 C8 C7 175.6(3) . . . . ? O3 N4 C8 C7 -2.8(4) . . . . ? O4 N4 C8 C9 -5.8(4) . . . . ? O3 N4 C8 C9 175.8(3) . . . . ? C9 C8 C7 C6 2.8(4) . . . . ? N4 C8 C7 C6 -178.6(2) . . . . ? C8 C7 C6 C5 6.5(4) . . . . ? C8 C7 C6 N3 -165.6(2) . . . . ? N2 C5 C6 C7 162.2(2) . . . . ? C10 C5 C6 C7 -13.2(4) . . . . ? N2 C5 C6 N3 -26.1(4) . . . . ? C10 C5 C6 N3 158.5(2) . . . . ? O2 N3 C6 C7 -29.8(4) . . . . ? O1 N3 C6 C7 146.3(2) . . . . ? O2 N3 C6 C5 158.0(3) . . . . ? O1 N3 C6 C5 -25.8(4) . . . . ? C5 N2 C11 C12 -124.2(2) . . . . ? C4 N2 C11 C12 56.8(3) . . . . ? N2 C11 C12 C13 -106.0(3) . . . . ? N2 C11 C12 C25 75.4(3) . . . . ? C25 C12 C13 C14 -178.5(2) . . . . ? C11 C12 C13 C14 2.9(4) . . . . ? C25 C12 C13 C18 1.6(4) . . . . ? C11 C12 C13 C18 -177.0(2) . . . . ? C12 C13 C14 C15 179.7(3) . . . . ? C18 C13 C14 C15 -0.4(4) . . . . ? C13 C14 C15 C16 1.3(5) . . . . ? C14 C15 C16 C17 -1.5(5) . . . . ? C15 C16 C17 C18 0.9(5) . . . . ? C16 C17 C18 C19 -179.7(3) . . . . ? C16 C17 C18 C13 -0.1(4) . . . . ? C12 C13 C18 C19 -0.7(4) . . . . ? C14 C13 C18 C19 179.4(2) . . . . ? C12 C13 C18 C17 179.7(2) . . . . ? C14 C13 C18 C17 -0.1(4) . . . . ? C17 C18 C19 C20 178.5(3) . . . . ? C13 C18 C19 C20 -1.0(4) . . . . ? C18 C19 C20 C21 -178.1(3) . . . . ? C18 C19 C20 C25 1.8(4) . . . . ? C19 C20 C21 C22 180.0(3) . . . . ? C25 C20 C21 C22 0.1(4) . . . . ? C20 C21 C22 C23 0.5(5) . . . . ? C21 C22 C23 C24 -0.4(5) . . . . ? C22 C23 C24 C25 -0.3(4) . . . . ? C13 C12 C25 C24 179.0(2) . . . . ? C11 C12 C25 C24 -2.4(3) . . . . ? C13 C12 C25 C20 -0.8(3) . . . . ? C11 C12 C25 C20 177.8(2) . . . . ? C23 C24 C25 C12 -178.9(2) . . . . ? C23 C24 C25 C20 0.9(4) . . . . ? C19 C20 C25 C12 -0.9(4) . . . . ? C21 C20 C25 C12 179.0(2) . . . . ? C19 C20 C25 C24 179.3(2) . . . . ? C21 C20 C25 C24 -0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.190 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.044 #===END data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 181 degree C _chemical_formula_moiety 'C25 H25 N3 O2' _chemical_formula_sum 'C25 H25 N3 O2' _chemical_formula_weight 399.48 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 1 2(1)/c 1 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 9.3950(2) _cell_length_b 21.4030(2) _cell_length_c 10.1200(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.792(6) _cell_angle_gamma 90.00 _cell_volume 2011.03(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28 _cell_measurement_theta_max +28 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type SADABS 2.1 _exptl_absorpt_correction_T_min 0.9849 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details SHELXTL _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD area detector _diffrn_measurement_method Phi-Omega scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13422 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4997 _reflns_number_gt 3582 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART 5.628 (Bruker, 2003) _computing_cell_refinement SMART 5.628 (Bruker, 2003) _computing_data_reduction SAINT+ 6.45 (Bruker, 2003) _computing_structure_solution SHELXTL 6.14 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1e _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0955P)^2^+1.3305P] 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 4997 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0857 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1585 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.36373(16) 0.03442(7) 0.27500(14) 0.0266(3) Uani 1 1 d . . . O2 O 0.19738(15) 0.06081(7) 0.11085(15) 0.0267(3) Uani 1 1 d . . . N1 N 0.54051(16) 0.18683(7) -0.45437(15) 0.0171(3) Uani 1 1 d . . . N2 N 0.74738(15) 0.10898(7) -0.15944(14) 0.0134(3) Uani 1 1 d . . . N3 N 0.32554(18) 0.05464(7) 0.16067(16) 0.0190(3) Uani 1 1 d . . . C1 C 0.5722(2) 0.15695(10) -0.57612(19) 0.0228(4) Uani 1 1 d . . . H1A H 0.5970 0.1140 -0.5580 0.034 Uiso 1 1 calc R . . H1B H 0.6516 0.1780 -0.6064 0.034 Uiso 1 1 calc R . . H1C H 0.4891 0.1593 -0.6441 0.034 Uiso 1 1 calc R . . C2 C 0.5037(2) 0.25202(9) -0.4825(2) 0.0256(4) Uani 1 1 d . . . H2A H 0.4240 0.2544 -0.5540 0.038 Uiso 1 1 calc R . . H2B H 0.5852 0.2734 -0.5080 0.038 Uiso 1 1 calc R . . H2C H 0.4776 0.2713 -0.4040 0.038 Uiso 1 1 calc R . . C3 C 0.6621(2) 0.18353(8) -0.34546(18) 0.0167(4) Uani 1 1 d . . . H3A H 0.6380 0.2062 -0.2689 0.020 Uiso 1 1 calc R . . H3B H 0.7450 0.2036 -0.3735 0.020 Uiso 1 1 calc R . . C4 C 0.70160(19) 0.11573(8) -0.30355(17) 0.0142(4) Uani 1 1 d . . . H4A H 0.6187 0.0891 -0.3307 0.017 Uiso 1 1 calc R . . H4B H 0.7786 0.1016 -0.3501 0.017 Uiso 1 1 calc R . . C5 C 0.64557(19) 0.09705(8) -0.07902(17) 0.0135(4) Uani 1 1 d . . . C6 C 0.68354(19) 0.07482(8) 0.05318(17) 0.0149(4) Uani 1 1 d . . . H6 H 0.7801 0.0689 0.0878 0.018 Uiso 1 1 calc R . . C7 C 0.5794(2) 0.06177(8) 0.13144(17) 0.0164(4) Uani 1 1 d . . . H7 H 0.6057 0.0468 0.2180 0.020 Uiso 1 1 calc R . . C8 C 0.4350(2) 0.07105(8) 0.08055(18) 0.0162(4) Uani 1 1 d . . . C9 C 0.39410(19) 0.09393(8) -0.04806(18) 0.0160(4) Uani 1 1 d . . . H9 H 0.2973 0.1007 -0.0805 0.019 Uiso 1 1 calc R . . C10 C 0.49721(19) 0.10650(8) -0.12713(17) 0.0149(4) Uani 1 1 d . . . H10 H 0.4693 0.1214 -0.2135 0.018 Uiso 1 1 calc R . . C11 C 0.90115(19) 0.10028(8) -0.10550(17) 0.0157(4) Uani 1 1 d . . . H11A H 0.9207 0.0560 -0.0938 0.019 Uiso 1 1 calc R . . H11B H 0.9212 0.1199 -0.0182 0.019 Uiso 1 1 calc R . . C12 C 1.00100(19) 0.12740(8) -0.19438(17) 0.0155(4) Uani 1 1 d . . . C13 C 1.02405(18) 0.19269(8) -0.19330(17) 0.0151(4) Uani 1 1 d . . . C14 C 0.9519(2) 0.23513(9) -0.11637(18) 0.0195(4) Uani 1 1 d . . . H14 H 0.8889 0.2195 -0.0621 0.023 Uiso 1 1 calc R . . C15 C 0.9740(2) 0.29804(9) -0.1212(2) 0.0229(4) Uani 1 1 d . . . H15 H 0.9261 0.3245 -0.0699 0.028 Uiso 1 1 calc R . . C16 C 1.0690(2) 0.32384(9) -0.2033(2) 0.0232(4) Uani 1 1 d . . . H16 H 1.0816 0.3669 -0.2069 0.028 Uiso 1 1 calc R . . C17 C 1.1411(2) 0.28544(9) -0.2763(2) 0.0216(4) Uani 1 1 d . . . H17 H 1.2038 0.3025 -0.3293 0.026 Uiso 1 1 calc R . . C18 C 1.12270(19) 0.21922(9) -0.27343(18) 0.0166(4) Uani 1 1 d . . . C19 C 1.19549(19) 0.17970(9) -0.34993(18) 0.0172(4) Uani 1 1 d . . . H19 H 1.2614 0.1967 -0.3997 0.021 Uiso 1 1 calc R . . C20 C 1.17226(19) 0.11556(8) -0.35386(17) 0.0154(4) Uani 1 1 d . . . C21 C 1.2460(2) 0.07610(9) -0.43524(18) 0.0177(4) Uani 1 1 d . . . H21 H 1.3115 0.0936 -0.4848 0.021 Uiso 1 1 calc R . . C22 C 1.2222(2) 0.01379(9) -0.44126(18) 0.0191(4) Uani 1 1 d . . . H22 H 1.2714 -0.0113 -0.4942 0.023 Uiso 1 1 calc R . . C23 C 1.1220(2) -0.01322(9) -0.36665(18) 0.0191(4) Uani 1 1 d . . . H23 H 1.1055 -0.0561 -0.3720 0.023 Uiso 1 1 calc R . . C24 C 1.0492(2) 0.02221(8) -0.28721(18) 0.0174(4) Uani 1 1 d . . . H24 H 0.9838 0.0032 -0.2396 0.021 Uiso 1 1 calc R . . C25 C 1.07184(18) 0.08844(8) -0.27588(17) 0.0145(4) 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 O1 0.0344(9) 0.0290(8) 0.0189(7) 0.0024(6) 0.0122(6) -0.0049(6) O2 0.0174(7) 0.0310(8) 0.0338(8) 0.0003(6) 0.0109(6) -0.0014(6) N1 0.0175(8) 0.0156(7) 0.0179(8) 0.0040(6) 0.0018(6) 0.0009(6) N2 0.0105(7) 0.0181(7) 0.0113(7) 0.0015(6) 0.0014(5) -0.0004(6) N3 0.0215(9) 0.0155(7) 0.0220(8) -0.0029(6) 0.0099(7) -0.0026(6) C1 0.0253(10) 0.0261(10) 0.0160(9) 0.0008(8) 0.0002(8) 0.0002(8) C2 0.0244(11) 0.0176(9) 0.0340(11) 0.0080(8) 0.0018(9) 0.0010(8) C3 0.0194(9) 0.0161(8) 0.0148(8) 0.0017(7) 0.0035(7) -0.0034(7) C4 0.0147(9) 0.0155(8) 0.0124(8) -0.0006(7) 0.0022(7) -0.0020(7) C5 0.0161(9) 0.0101(8) 0.0148(8) -0.0016(6) 0.0042(7) -0.0003(6) C6 0.0130(8) 0.0167(8) 0.0153(8) 0.0009(7) 0.0025(7) 0.0018(7) C7 0.0209(9) 0.0160(8) 0.0129(8) -0.0004(7) 0.0042(7) -0.0015(7) C8 0.0185(9) 0.0145(8) 0.0169(9) -0.0016(7) 0.0070(7) -0.0020(7) C9 0.0107(8) 0.0160(8) 0.0213(9) -0.0029(7) 0.0024(7) -0.0014(7) C10 0.0154(9) 0.0152(8) 0.0139(8) 0.0010(7) 0.0013(7) 0.0006(7) C11 0.0139(9) 0.0192(9) 0.0139(8) 0.0013(7) 0.0020(7) 0.0005(7) C12 0.0109(8) 0.0202(9) 0.0151(8) 0.0024(7) 0.0007(7) -0.0010(7) C13 0.0111(8) 0.0195(9) 0.0138(8) -0.0005(7) -0.0011(6) 0.0002(7) C14 0.0167(9) 0.0245(10) 0.0176(9) -0.0031(7) 0.0035(7) -0.0024(8) C15 0.0210(10) 0.0236(10) 0.0245(10) -0.0090(8) 0.0042(8) 0.0014(8) C16 0.0239(10) 0.0176(9) 0.0276(10) -0.0031(8) 0.0021(8) -0.0027(8) C17 0.0220(10) 0.0186(9) 0.0245(10) 0.0002(8) 0.0044(8) -0.0034(8) C18 0.0136(9) 0.0195(9) 0.0165(9) -0.0005(7) 0.0012(7) 0.0000(7) C19 0.0135(9) 0.0210(9) 0.0172(9) 0.0015(7) 0.0034(7) -0.0026(7) C20 0.0111(8) 0.0199(9) 0.0142(8) 0.0021(7) -0.0011(7) 0.0016(7) C21 0.0145(9) 0.0229(9) 0.0162(9) 0.0002(7) 0.0039(7) 0.0000(7) C22 0.0181(9) 0.0218(9) 0.0176(9) -0.0011(7) 0.0038(7) 0.0053(7) C23 0.0202(10) 0.0165(9) 0.0198(9) 0.0012(7) 0.0003(7) 0.0000(7) C24 0.0141(9) 0.0195(9) 0.0186(9) 0.0042(7) 0.0019(7) -0.0002(7) C25 0.0100(8) 0.0178(8) 0.0148(8) 0.0021(7) -0.0010(6) -0.0003(7) _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 N3 1.236(2) . ? O2 N3 1.239(2) . ? N1 C2 1.455(2) . ? N1 C1 1.459(2) . ? N1 C3 1.463(2) . ? N2 C5 1.371(2) . ? N2 C4 1.463(2) . ? N2 C11 1.476(2) . ? N3 C8 1.447(2) . ? C3 C4 1.541(2) . ? C5 C6 1.413(2) . ? C5 C10 1.419(2) . ? C6 C7 1.378(2) . ? C7 C8 1.390(3) . ? C8 C9 1.389(3) . ? C9 C10 1.374(2) . ? C11 C12 1.511(2) . ? C12 C25 1.409(2) . ? C12 C13 1.414(2) . ? C13 C14 1.432(2) . ? C13 C18 1.438(2) . ? C14 C15 1.364(3) . ? C15 C16 1.421(3) . ? C16 C17 1.354(3) . ? C17 C18 1.429(3) . ? C18 C19 1.394(2) . ? C19 C20 1.390(3) . ? C20 C21 1.431(2) . ? C20 C25 1.441(2) . ? C21 C22 1.352(3) . ? C22 C23 1.417(3) . ? C23 C24 1.363(3) . ? C24 C25 1.435(2) . ? 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 C2 N1 C1 109.16(15) . . ? C2 N1 C3 109.18(15) . . ? C1 N1 C3 112.24(15) . . ? C5 N2 C4 118.98(14) . . ? C5 N2 C11 119.28(14) . . ? C4 N2 C11 120.20(14) . . ? O1 N3 O2 122.90(16) . . ? O1 N3 C8 118.69(16) . . ? O2 N3 C8 118.40(16) . . ? N1 C3 C4 112.37(14) . . ? N2 C4 C3 112.90(14) . . ? N2 C5 C6 121.77(16) . . ? N2 C5 C10 120.50(16) . . ? C6 C5 C10 117.74(16) . . ? C7 C6 C5 120.91(17) . . ? C6 C7 C8 119.77(17) . . ? C9 C8 C7 120.82(16) . . ? C9 C8 N3 119.49(17) . . ? C7 C8 N3 119.65(16) . . ? C10 C9 C8 119.74(17) . . ? C9 C10 C5 121.01(17) . . ? N2 C11 C12 113.14(14) . . ? C25 C12 C13 120.25(16) . . ? C25 C12 C11 120.84(16) . . ? C13 C12 C11 118.90(16) . . ? C12 C13 C14 123.12(16) . . ? C12 C13 C18 119.80(16) . . ? C14 C13 C18 117.07(16) . . ? C15 C14 C13 121.29(17) . . ? C14 C15 C16 121.14(18) . . ? C17 C16 C15 119.63(18) . . ? C16 C17 C18 121.27(18) . . ? C19 C18 C17 121.30(17) . . ? C19 C18 C13 119.11(16) . . ? C17 C18 C13 119.57(16) . . ? C20 C19 C18 121.80(16) . . ? C19 C20 C21 120.79(16) . . ? C19 C20 C25 119.68(16) . . ? C21 C20 C25 119.52(16) . . ? C22 C21 C20 121.11(17) . . ? C21 C22 C23 119.83(17) . . ? C24 C23 C22 121.44(17) . . ? C23 C24 C25 120.98(17) . . ? C12 C25 C24 123.60(16) . . ? C12 C25 C20 119.30(16) . . ? C24 C25 C20 117.10(16) . . ? 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 C2 N1 C3 C4 176.38(15) . . . . ? C1 N1 C3 C4 -62.44(19) . . . . ? C5 N2 C4 C3 89.25(18) . . . . ? C11 N2 C4 C3 -104.99(17) . . . . ? N1 C3 C4 N2 -143.47(15) . . . . ? C4 N2 C5 C6 163.98(15) . . . . ? C11 N2 C5 C6 -1.9(2) . . . . ? C4 N2 C5 C10 -15.7(2) . . . . ? C11 N2 C5 C10 178.42(15) . . . . ? N2 C5 C6 C7 -178.53(16) . . . . ? C10 C5 C6 C7 1.2(2) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? C6 C7 C8 N3 177.20(16) . . . . ? O1 N3 C8 C9 -179.90(16) . . . . ? O2 N3 C8 C9 0.9(2) . . . . ? O1 N3 C8 C7 2.3(2) . . . . ? O2 N3 C8 C7 -176.90(16) . . . . ? C7 C8 C9 C10 1.2(3) . . . . ? N3 C8 C9 C10 -176.60(15) . . . . ? C8 C9 C10 C5 -0.6(3) . . . . ? N2 C5 C10 C9 179.14(16) . . . . ? C6 C5 C10 C9 -0.5(2) . . . . ? C5 N2 C11 C12 -168.27(15) . . . . ? C4 N2 C11 C12 26.0(2) . . . . ? N2 C11 C12 C25 -103.16(19) . . . . ? N2 C11 C12 C13 77.7(2) . . . . ? C25 C12 C13 C14 177.84(17) . . . . ? C11 C12 C13 C14 -3.0(3) . . . . ? C25 C12 C13 C18 -1.4(3) . . . . ? C11 C12 C13 C18 177.73(16) . . . . ? C12 C13 C14 C15 -178.02(18) . . . . ? C18 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C19 179.14(18) . . . . ? C16 C17 C18 C13 1.0(3) . . . . ? C12 C13 C18 C19 -0.7(3) . . . . ? C14 C13 C18 C19 179.95(17) . . . . ? C12 C13 C18 C17 177.42(17) . . . . ? C14 C13 C18 C17 -1.9(3) . . . . ? C17 C18 C19 C20 -176.26(17) . . . . ? C13 C18 C19 C20 1.9(3) . . . . ? C18 C19 C20 C21 178.71(17) . . . . ? C18 C19 C20 C25 -0.8(3) . . . . ? C19 C20 C21 C22 -178.89(18) . . . . ? C25 C20 C21 C22 0.6(3) . . . . ? C20 C21 C22 C23 0.4(3) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C23 C24 C25 -0.2(3) . . . . ? C13 C12 C25 C24 -177.03(17) . . . . ? C11 C12 C25 C24 3.8(3) . . . . ? C13 C12 C25 C20 2.5(3) . . . . ? C11 C12 C25 C20 -176.66(15) . . . . ? C23 C24 C25 C12 -179.30(17) . . . . ? C23 C24 C25 C20 1.2(3) . . . . ? C19 C20 C25 C12 -1.4(3) . . . . ? C21 C20 C25 C12 179.09(16) . . . . ? C19 C20 C25 C24 178.15(16) . . . . ? C21 C20 C25 C24 -1.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.394 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.059 #===END data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 189 degree C _chemical_formula_moiety 'C24 H24 N4 O2' _chemical_formula_sum 'C24 H24 N4 O2' _chemical_formula_weight 400.47 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 1 21/c 1 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 12.453(2) _cell_length_b 6.328(4) _cell_length_c 26.349(2) _cell_angle_alpha 90.10(1) _cell_angle_beta 93.88(5) _cell_angle_gamma 90.10(1) _cell_volume 2071.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11 _cell_measurement_theta_max 16 _exptl_crystal_description Blocks _exptl_crystal_colour Light Yellow _exptl_crystal_size_max 0.20 mm _exptl_crystal_size_mid 0.18 mm _exptl_crystal_size_min 0.23 mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9810 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Enraf-Nonius cad4 Mach2 _diffrn_measurement_method theta-2theta scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1 h _diffrn_standards_decay_% <1 _diffrn_reflns_number 2848 _diffrn_reflns_av_R_equivalents 0.2369 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 22.48 _reflns_number_total 2702 _reflns_number_gt 1413 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 Mach2 _computing_cell_refinement CAD4 _computing_data_reduction SHELXL-97 _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1 _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0799P)^2^+0.0000P] 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 2702 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1557 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.000 _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 O1 O 0.3261(3) 0.6953(6) 0.06151(15) 0.1054(13) Uani 1 1 d . . . O2 O 0.4038(3) 0.8386(6) 0.12695(15) 0.1032(13) Uani 1 1 d . . . N1 N 0.7795(3) -0.2522(6) 0.00061(12) 0.0601(9) Uani 1 1 d . . . N2 N 0.7134(2) 0.0904(5) 0.11031(10) 0.0419(8) Uani 1 1 d . . . N3 N 0.6405(2) 0.4022(5) 0.13680(11) 0.0463(8) Uani 1 1 d . . . N4 N 0.3981(3) 0.7006(7) 0.09489(17) 0.0681(11) Uani 1 1 d . . . C1 C 0.8154(5) -0.2066(10) -0.04975(18) 0.108(2) Uani 1 1 d . . . H1A H 0.8136 -0.3339 -0.0697 0.162 Uiso 1 1 calc R . . H1B H 0.8876 -0.1524 -0.0465 0.162 Uiso 1 1 calc R . . H1C H 0.7687 -0.1035 -0.0662 0.162 Uiso 1 1 calc R . . C2 C 0.8456(4) -0.4183(8) 0.02532(19) 0.0935(17) Uani 1 1 d . . . H2A H 0.8428 -0.5424 0.0043 0.140 Uiso 1 1 calc R . . H2B H 0.8188 -0.4514 0.0577 0.140 Uiso 1 1 calc R . . H2C H 0.9188 -0.3702 0.0302 0.140 Uiso 1 1 calc R . . C3 C 0.7796(3) -0.0612(7) 0.03161(14) 0.0543(11) Uani 1 1 d . . . H3A H 0.7481 0.0541 0.0115 0.065 Uiso 1 1 calc R . . H3B H 0.8532 -0.0228 0.0423 0.065 Uiso 1 1 calc R . . C4 C 0.7167(3) -0.0942(6) 0.07784(13) 0.0440(10) Uani 1 1 d . . . H4A H 0.6436 -0.1343 0.0668 0.053 Uiso 1 1 calc R . . H4B H 0.7485 -0.2103 0.0975 0.053 Uiso 1 1 calc R . . C5 C 0.6354(3) 0.2391(6) 0.10376(13) 0.0406(9) Uani 1 1 d . . . C6 C 0.5515(3) 0.2257(7) 0.06491(14) 0.0529(11) Uani 1 1 d . . . H6 H 0.5501 0.1151 0.0416 0.063 Uiso 1 1 calc R . . C7 C 0.4734(3) 0.3744(7) 0.06179(16) 0.0563(11) Uani 1 1 d . . . H7 H 0.4175 0.3670 0.0366 0.068 Uiso 1 1 calc R . . C8 C 0.4783(3) 0.5373(6) 0.09684(15) 0.0481(10) Uani 1 1 d . . . C9 C 0.5624(3) 0.5445(7) 0.13287(14) 0.0494(10) Uani 1 1 d . . . H9 H 0.5650 0.6558 0.1560 0.059 Uiso 1 1 calc R . . C10 C 0.8046(3) 0.1217(6) 0.14796(14) 0.0458(10) Uani 1 1 d . . . H10A H 0.7881 0.2365 0.1706 0.055 Uiso 1 1 calc R . . H10B H 0.8676 0.1621 0.1305 0.055 Uiso 1 1 calc R . . C11 C 0.8301(3) -0.0739(6) 0.17907(12) 0.0394(9) Uani 1 1 d . . . C12 C 0.9225(3) -0.1962(6) 0.17192(13) 0.0416(10) Uani 1 1 d . . . C13 C 1.0041(3) -0.1372(7) 0.13919(14) 0.0561(12) Uani 1 1 d . . . H13 H 0.9964 -0.0119 0.1209 0.067 Uiso 1 1 calc R . . C14 C 1.0924(3) -0.2578(8) 0.13389(15) 0.0675(13) Uani 1 1 d . . . H14 H 1.1445 -0.2142 0.1125 0.081 Uiso 1 1 calc R . . C15 C 1.1055(3) -0.4494(8) 0.16081(16) 0.0673(13) Uani 1 1 d . . . H15 H 1.1665 -0.5313 0.1572 0.081 Uiso 1 1 calc R . . C16 C 1.0308(3) -0.5144(7) 0.19157(15) 0.0584(12) Uani 1 1 d . . . H16 H 1.0399 -0.6430 0.2083 0.070 Uiso 1 1 calc R . . C17 C 0.9380(3) -0.3907(6) 0.19918(13) 0.0422(10) Uani 1 1 d . . . C18 C 0.8640(3) -0.4527(6) 0.23271(13) 0.0470(10) Uani 1 1 d . . . H18 H 0.8738 -0.5813 0.2494 0.056 Uiso 1 1 calc R . . C19 C 0.7759(3) -0.3311(6) 0.24245(14) 0.0454(10) Uani 1 1 d . . . C20 C 0.7047(3) -0.3892(7) 0.27961(15) 0.0552(11) Uani 1 1 d . . . H20 H 0.7157 -0.5157 0.2971 0.066 Uiso 1 1 calc R . . C21 C 0.6213(3) -0.2655(8) 0.29031(16) 0.0660(13) Uani 1 1 d . . . H21 H 0.5758 -0.3062 0.3151 0.079 Uiso 1 1 calc R . . C22 C 0.6033(3) -0.0757(8) 0.26401(15) 0.0674(13) Uani 1 1 d . . . H22 H 0.5456 0.0091 0.2716 0.081 Uiso 1 1 calc R . . C23 C 0.6681(3) -0.0132(7) 0.22774(14) 0.0538(11) Uani 1 1 d . . . H23 H 0.6535 0.1126 0.2105 0.065 Uiso 1 1 calc R . . C24 C 0.7588(3) -0.1368(6) 0.21539(14) 0.0405(10) 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 O1 0.087(3) 0.113(3) 0.112(3) -0.010(2) -0.024(2) 0.049(2) O2 0.103(3) 0.085(3) 0.120(3) -0.032(2) -0.003(2) 0.046(2) N1 0.073(2) 0.055(2) 0.053(2) -0.009(2) 0.0088(18) 0.009(2) N2 0.0430(17) 0.041(2) 0.0406(18) -0.0043(16) -0.0028(14) 0.0076(16) N3 0.0491(19) 0.041(2) 0.0485(19) -0.0047(18) 0.0023(15) 0.0070(18) N4 0.063(3) 0.069(3) 0.073(3) 0.004(2) 0.010(2) 0.025(2) C1 0.153(5) 0.115(5) 0.061(3) -0.013(3) 0.044(3) 0.020(4) C2 0.121(4) 0.066(4) 0.094(4) -0.018(3) 0.008(3) 0.035(3) C3 0.058(3) 0.054(3) 0.051(2) 0.001(2) 0.009(2) 0.004(2) C4 0.047(2) 0.037(2) 0.047(2) 0.000(2) -0.0022(18) 0.0067(19) C5 0.041(2) 0.045(3) 0.036(2) 0.004(2) 0.0046(17) 0.002(2) C6 0.056(2) 0.057(3) 0.045(2) -0.009(2) -0.006(2) 0.015(2) C7 0.051(2) 0.065(3) 0.052(3) -0.004(2) -0.0042(19) 0.011(2) C8 0.044(2) 0.049(3) 0.052(3) 0.009(2) 0.008(2) 0.011(2) C9 0.052(2) 0.042(3) 0.055(3) -0.006(2) 0.014(2) 0.001(2) C10 0.040(2) 0.047(3) 0.050(2) 0.001(2) -0.0035(18) 0.003(2) C11 0.037(2) 0.045(2) 0.036(2) -0.0044(19) -0.0005(17) 0.0008(19) C12 0.037(2) 0.049(3) 0.038(2) -0.001(2) -0.0063(17) 0.0014(19) C13 0.048(2) 0.069(3) 0.052(3) 0.004(2) 0.004(2) 0.009(2) C14 0.050(3) 0.103(4) 0.051(3) 0.010(3) 0.011(2) 0.015(3) C15 0.055(3) 0.091(4) 0.056(3) -0.008(3) 0.000(2) 0.032(3) C16 0.053(3) 0.067(3) 0.053(3) -0.002(2) -0.007(2) 0.016(2) C17 0.041(2) 0.047(3) 0.038(2) -0.008(2) -0.0082(18) 0.005(2) C18 0.055(3) 0.038(2) 0.047(2) 0.000(2) -0.009(2) 0.000(2) C19 0.037(2) 0.051(3) 0.047(2) -0.002(2) -0.0046(19) -0.006(2) C20 0.046(2) 0.058(3) 0.061(3) 0.007(2) 0.002(2) -0.010(2) C21 0.052(3) 0.090(4) 0.058(3) 0.009(3) 0.011(2) -0.011(3) C22 0.051(3) 0.096(4) 0.057(3) 0.005(3) 0.015(2) 0.017(3) C23 0.050(2) 0.063(3) 0.048(2) -0.001(2) 0.000(2) 0.014(2) C24 0.035(2) 0.043(2) 0.042(2) -0.007(2) -0.0069(17) 0.0024(19) _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 N4 1.213(4) . ? O2 N4 1.213(5) . ? N1 C3 1.458(5) . ? N1 C1 1.458(5) . ? N1 C2 1.463(5) . ? N2 C5 1.357(4) . ? N2 C4 1.449(4) . ? N2 C10 1.470(4) . ? N3 C9 1.326(5) . ? N3 C5 1.348(4) . ? N4 C8 1.437(5) . ? C3 C4 1.507(5) . ? C5 C6 1.414(5) . ? C6 C7 1.354(5) . ? C7 C8 1.381(5) . ? C8 C9 1.366(5) . ? C10 C11 1.508(5) . ? C11 C24 1.407(5) . ? C11 C12 1.410(5) . ? C12 C13 1.426(5) . ? C12 C17 1.433(5) . ? C13 C14 1.355(5) . ? C14 C15 1.410(6) . ? C15 C16 1.339(5) . ? C16 C17 1.423(5) . ? C17 C18 1.376(5) . ? C18 C19 1.379(5) . ? C19 C20 1.414(5) . ? C19 C24 1.431(5) . ? C20 C21 1.346(5) . ? C21 C22 1.399(6) . ? C22 C23 1.352(5) . ? C23 C24 1.429(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 C3 N1 C1 110.9(4) . . ? C3 N1 C2 111.6(3) . . ? C1 N1 C2 110.5(4) . . ? C5 N2 C4 122.2(3) . . ? C5 N2 C10 120.6(3) . . ? C4 N2 C10 117.0(3) . . ? C9 N3 C5 117.9(3) . . ? O1 N4 O2 121.9(4) . . ? O1 N4 C8 119.0(4) . . ? O2 N4 C8 119.1(4) . . ? N1 C3 C4 110.9(3) . . ? N2 C4 C3 113.7(3) . . ? N3 C5 N2 116.5(3) . . ? N3 C5 C6 120.8(4) . . ? N2 C5 C6 122.6(4) . . ? C7 C6 C5 119.8(4) . . ? C6 C7 C8 118.6(4) . . ? C9 C8 C7 119.0(4) . . ? C9 C8 N4 120.1(4) . . ? C7 C8 N4 120.9(4) . . ? N3 C9 C8 123.9(4) . . ? N2 C10 C11 112.5(3) . . ? C24 C11 C12 119.6(3) . . ? C24 C11 C10 118.9(3) . . ? C12 C11 C10 121.5(3) . . ? C11 C12 C13 123.9(4) . . ? C11 C12 C17 119.3(3) . . ? C13 C12 C17 116.8(3) . . ? C14 C13 C12 122.1(4) . . ? C13 C14 C15 120.1(4) . . ? C16 C15 C14 120.5(4) . . ? C15 C16 C17 121.4(4) . . ? C18 C17 C16 121.3(4) . . ? C18 C17 C12 119.6(3) . . ? C16 C17 C12 119.1(4) . . ? C17 C18 C19 122.4(4) . . ? C18 C19 C20 121.9(4) . . ? C18 C19 C24 118.8(3) . . ? C20 C19 C24 119.3(4) . . ? C21 C20 C19 121.5(4) . . ? C20 C21 C22 119.8(4) . . ? C23 C22 C21 121.2(4) . . ? C22 C23 C24 121.3(4) . . ? C11 C24 C23 123.0(4) . . ? C11 C24 C19 120.2(3) . . ? C23 C24 C19 116.8(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 C1 N1 C3 C4 165.4(4) . . . . ? C2 N1 C3 C4 -71.0(4) . . . . ? C5 N2 C4 C3 89.5(4) . . . . ? C10 N2 C4 C3 -84.7(4) . . . . ? N1 C3 C4 N2 -179.9(3) . . . . ? C9 N3 C5 N2 -176.8(3) . . . . ? C9 N3 C5 C6 2.6(5) . . . . ? C4 N2 C5 N3 179.3(3) . . . . ? C10 N2 C5 N3 -6.7(5) . . . . ? C4 N2 C5 C6 0.0(5) . . . . ? C10 N2 C5 C6 174.0(4) . . . . ? N3 C5 C6 C7 -2.2(6) . . . . ? N2 C5 C6 C7 177.1(4) . . . . ? C5 C6 C7 C8 0.4(6) . . . . ? C6 C7 C8 C9 1.0(6) . . . . ? C6 C7 C8 N4 179.3(4) . . . . ? O1 N4 C8 C9 177.4(4) . . . . ? O2 N4 C8 C9 -3.3(6) . . . . ? O1 N4 C8 C7 -0.8(6) . . . . ? O2 N4 C8 C7 178.5(4) . . . . ? C5 N3 C9 C8 -1.2(5) . . . . ? C7 C8 C9 N3 -0.6(6) . . . . ? N4 C8 C9 N3 -178.9(4) . . . . ? C5 N2 C10 C11 135.6(3) . . . . ? C4 N2 C10 C11 -50.1(4) . . . . ? N2 C10 C11 C24 -71.4(4) . . . . ? N2 C10 C11 C12 107.5(4) . . . . ? C24 C11 C12 C13 -174.7(3) . . . . ? C10 C11 C12 C13 6.4(5) . . . . ? C24 C11 C12 C17 4.5(5) . . . . ? C10 C11 C12 C17 -174.4(3) . . . . ? C11 C12 C13 C14 179.1(4) . . . . ? C17 C12 C13 C14 -0.1(5) . . . . ? C12 C13 C14 C15 0.6(6) . . . . ? C13 C14 C15 C16 0.3(6) . . . . ? C14 C15 C16 C17 -1.7(6) . . . . ? C15 C16 C17 C18 -176.8(4) . . . . ? C15 C16 C17 C12 2.2(5) . . . . ? C11 C12 C17 C18 -1.5(5) . . . . ? C13 C12 C17 C18 177.7(3) . . . . ? C11 C12 C17 C16 179.5(3) . . . . ? C13 C12 C17 C16 -1.2(5) . . . . ? C16 C17 C18 C19 177.0(3) . . . . ? C12 C17 C18 C19 -1.9(5) . . . . ? C17 C18 C19 C20 -175.4(3) . . . . ? C17 C18 C19 C24 2.2(5) . . . . ? C18 C19 C20 C21 177.3(4) . . . . ? C24 C19 C20 C21 -0.3(6) . . . . ? C19 C20 C21 C22 0.6(6) . . . . ? C20 C21 C22 C23 0.1(6) . . . . ? C21 C22 C23 C24 -1.0(6) . . . . ? C12 C11 C24 C23 175.0(3) . . . . ? C10 C11 C24 C23 -6.1(5) . . . . ? C12 C11 C24 C19 -4.2(5) . . . . ? C10 C11 C24 C19 174.7(3) . . . . ? C22 C23 C24 C11 -177.9(4) . . . . ? C22 C23 C24 C19 1.3(5) . . . . ? C18 C19 C24 C11 0.9(5) . . . . ? C20 C19 C24 C11 178.6(3) . . . . ? C18 C19 C24 C23 -178.3(3) . . . . ? C20 C19 C24 C23 -0.6(5) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.215 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.056 #===END data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 66 degree C _chemical_formula_moiety C10 H14 N4 O4 _chemical_formula_sum 'C10 H14 N4 O4' _chemical_formula_weight 254.25 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 Triclinic _symmetry_space_group_name_H-M P -1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4860(2) _cell_length_b 10.5560(2) _cell_length_c 10.6300(2) _cell_angle_alpha 83.381(4) _cell_angle_beta 75.653(6) _cell_angle_gamma 79.621(3) _cell_volume 585.02(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description Rectangular Parallelepiped _exptl_crystal_colour Orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Enraf-Nonius CAD4 Mach2 _diffrn_measurement_method Theta-2Theta scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1h _diffrn_standards_decay_% <1% _diffrn_reflns_number 1734 _diffrn_reflns_av_R_equivalents 0.2342 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 22.65 _reflns_number_total 1541 _reflns_number_gt 1113 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 Mach2 _computing_cell_refinement CAD4 _computing_data_reduction SHELXL-97 _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1e _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1911P)^2^+0.0000P] 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 1541 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1179 _refine_ls_R_factor_gt 0.0852 _refine_ls_wR_factor_ref 0.2429 _refine_ls_wR_factor_gt 0.2209 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _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 O1 O 0.5226(6) 0.0662(3) 0.6003(3) 0.0592(10) Uani 1 1 d . . . O2 O 0.4566(6) 0.1788(3) 0.7633(3) 0.0576(10) Uani 1 1 d . . . O3 O 1.0015(7) 0.4585(4) 0.7963(3) 0.0742(12) Uani 1 1 d . . . O4 O 1.3213(6) 0.4890(3) 0.6416(3) 0.0653(11) Uani 1 1 d . . . N1 N 0.6614(6) 0.2174(3) 0.1372(3) 0.0390(9) Uani 1 1 d . . . N2 N 0.8642(6) 0.1151(3) 0.3858(3) 0.0427(9) Uani 1 1 d . . . H2 H 0.7422 0.0719 0.4201 0.064 Uiso 1 1 calc R . . N4 N 1.1313(7) 0.4400(3) 0.6883(3) 0.0453(10) Uani 1 1 d . . . N3 N 0.5770(6) 0.1503(3) 0.6555(3) 0.0411(9) Uani 1 1 d . . . C1 C 0.5699(9) 0.3458(5) 0.0845(5) 0.0592(13) Uani 1 1 d . . . H1A H 0.4034 0.3475 0.0701 0.089 Uiso 1 1 calc R . . H1B H 0.6846 0.3664 0.0036 0.089 Uiso 1 1 calc R . . H1C H 0.5614 0.4080 0.1452 0.089 Uiso 1 1 calc R . . C2 C 0.6704(9) 0.1219(5) 0.0475(5) 0.0577(13) Uani 1 1 d . . . H2A H 0.5032 0.1246 0.0334 0.087 Uiso 1 1 calc R . . H2B H 0.7280 0.0375 0.0837 0.087 Uiso 1 1 calc R . . H2C H 0.7857 0.1404 -0.0339 0.087 Uiso 1 1 calc R . . C3 C 0.9110(7) 0.2136(4) 0.1591(4) 0.0433(11) Uani 1 1 d . . . H3A H 0.9155 0.2932 0.1951 0.052 Uiso 1 1 calc R . . H3B H 1.0342 0.2094 0.0760 0.052 Uiso 1 1 calc R . . C4 C 0.9902(8) 0.1011(4) 0.2497(4) 0.0475(11) Uani 1 1 d . . . H4A H 0.9534 0.0229 0.2236 0.057 Uiso 1 1 calc R . . H4B H 1.1729 0.0912 0.2405 0.057 Uiso 1 1 calc R . . C5 C 0.9276(7) 0.1919(4) 0.4613(4) 0.0365(10) Uani 1 1 d . . . C10 C 1.1382(7) 0.2551(4) 0.4143(4) 0.0409(11) Uani 1 1 d . . . H10 H 1.2367 0.2415 0.3308 0.049 Uiso 1 1 calc R . . C9 C 1.2044(7) 0.3359(4) 0.4862(4) 0.0407(10) Uani 1 1 d . . . H9 H 1.3438 0.3781 0.4516 0.049 Uiso 1 1 calc R . . C8 C 1.0612(7) 0.3548(4) 0.6121(4) 0.0369(10) Uani 1 1 d . . . C7 C 0.8581(7) 0.2961(4) 0.6635(4) 0.0379(10) Uani 1 1 d . . . H7 H 0.7627 0.3114 0.7473 0.045 Uiso 1 1 calc R . . C6 C 0.7898(7) 0.2114(4) 0.5904(4) 0.0359(10) 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 O1 0.060(2) 0.063(2) 0.065(2) -0.0006(17) -0.0157(15) -0.0367(16) O2 0.0539(19) 0.079(2) 0.0407(18) 0.0002(15) 0.0004(14) -0.0325(16) O3 0.077(2) 0.090(3) 0.061(2) -0.033(2) 0.0070(18) -0.043(2) O4 0.056(2) 0.078(2) 0.071(2) -0.0160(18) -0.0040(16) -0.0415(18) N1 0.0344(18) 0.046(2) 0.0372(19) -0.0046(15) -0.0057(14) -0.0092(14) N2 0.050(2) 0.044(2) 0.0385(19) 0.0022(15) -0.0159(15) -0.0145(16) N4 0.045(2) 0.047(2) 0.049(2) -0.0108(17) -0.0084(17) -0.0192(17) N3 0.040(2) 0.043(2) 0.045(2) 0.0095(16) -0.0171(16) -0.0187(16) C1 0.052(3) 0.063(3) 0.060(3) 0.008(2) -0.015(2) -0.006(2) C2 0.057(3) 0.064(3) 0.058(3) -0.009(2) -0.023(2) -0.010(2) C3 0.042(2) 0.055(3) 0.037(2) -0.0045(19) -0.0099(17) -0.0160(19) C4 0.057(3) 0.051(3) 0.037(2) -0.0102(19) -0.0182(19) 0.000(2) C5 0.042(2) 0.036(2) 0.034(2) -0.0028(17) -0.0159(17) -0.0035(17) C10 0.040(2) 0.048(2) 0.034(2) -0.0012(18) -0.0065(17) -0.0085(18) C9 0.033(2) 0.046(2) 0.045(2) 0.0020(18) -0.0100(17) -0.0126(18) C8 0.034(2) 0.039(2) 0.041(2) -0.0035(17) -0.0094(17) -0.0115(17) C7 0.036(2) 0.043(2) 0.034(2) -0.0034(18) -0.0081(16) -0.0053(18) C6 0.032(2) 0.037(2) 0.042(2) 0.0028(17) -0.0130(16) -0.0095(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 O1 N3 1.235(5) . ? O2 N3 1.213(4) . ? O3 N4 1.208(4) . ? O4 N4 1.216(4) . ? N1 C3 1.438(5) . ? N1 C2 1.452(5) . ? N1 C1 1.457(6) . ? N2 C5 1.346(5) . ? N2 C4 1.452(5) . ? N4 C8 1.435(5) . ? N3 C6 1.424(5) . ? C3 C4 1.511(6) . ? C5 C10 1.394(6) . ? C5 C6 1.411(5) . ? C10 C9 1.357(6) . ? C9 C8 1.390(6) . ? C8 C7 1.339(5) . ? C7 C6 1.403(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 C3 N1 C2 109.8(3) . . ? C3 N1 C1 110.0(3) . . ? C2 N1 C1 110.1(3) . . ? C5 N2 C4 123.7(3) . . ? O3 N4 O4 122.9(3) . . ? O3 N4 C8 118.8(3) . . ? O4 N4 C8 118.3(3) . . ? O2 N3 O1 121.3(3) . . ? O2 N3 C6 120.6(3) . . ? O1 N3 C6 118.1(3) . . ? N1 C3 C4 114.1(3) . . ? N2 C4 C3 113.8(3) . . ? N2 C5 C10 120.6(3) . . ? N2 C5 C6 122.6(4) . . ? C10 C5 C6 116.9(3) . . ? C9 C10 C5 122.3(4) . . ? C10 C9 C8 119.2(4) . . ? C7 C8 C9 121.4(3) . . ? C7 C8 N4 119.3(3) . . ? C9 C8 N4 119.3(3) . . ? C8 C7 C6 119.7(4) . . ? C7 C6 C5 120.4(3) . . ? C7 C6 N3 115.3(3) . . ? C5 C6 N3 124.3(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 C2 N1 C3 C4 -76.5(4) . . . . ? C1 N1 C3 C4 162.3(3) . . . . ? C5 N2 C4 C3 -76.7(5) . . . . ? N1 C3 C4 N2 -74.4(4) . . . . ? C4 N2 C5 C10 -5.8(6) . . . . ? C4 N2 C5 C6 175.1(3) . . . . ? N2 C5 C10 C9 178.3(3) . . . . ? C6 C5 C10 C9 -2.5(6) . . . . ? C5 C10 C9 C8 1.3(6) . . . . ? C10 C9 C8 C7 -0.7(6) . . . . ? C10 C9 C8 N4 179.9(3) . . . . ? O3 N4 C8 C7 -1.5(6) . . . . ? O4 N4 C8 C7 177.6(4) . . . . ? O3 N4 C8 C9 178.0(4) . . . . ? O4 N4 C8 C9 -3.0(6) . . . . ? C9 C8 C7 C6 1.4(6) . . . . ? N4 C8 C7 C6 -179.2(3) . . . . ? C8 C7 C6 C5 -2.6(6) . . . . ? C8 C7 C6 N3 177.7(3) . . . . ? N2 C5 C6 C7 -177.7(3) . . . . ? C10 C5 C6 C7 3.1(5) . . . . ? N2 C5 C6 N3 1.9(6) . . . . ? C10 C5 C6 N3 -177.3(3) . . . . ? O2 N3 C6 C7 4.9(5) . . . . ? O1 N3 C6 C7 -173.6(3) . . . . ? O2 N3 C6 C5 -174.7(4) . . . . ? O1 N3 C6 C5 6.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 22.65 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.379 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.124 #===END data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 172 degree C _chemical_formula_moiety 'C23 H20 N4 O4' _chemical_formula_sum 'C23 H20 N4 O4' _chemical_formula_weight 416.43 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 1 2(1)1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9210(8) _cell_length_b 14.2947(14) _cell_length_c 8.7995(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.710(2) _cell_angle_gamma 90.00 _cell_volume 995.91(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28 _cell_measurement_theta_max +28 _exptl_crystal_description Prism _exptl_crystal_colour Pale Brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type SADABS 2.1 _exptl_absorpt_correction_T_min 0.9827 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details SHELXTL _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD area detector _diffrn_measurement_method Phi-Omega scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6689 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4277 _reflns_number_gt 3748 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART 5.628 (Bruker, 2003) _computing_cell_refinement SMART 5.628 (Bruker, 2003) _computing_data_reduction SAINT+ 6.45 (Bruker, 2003) _computing_structure_solution SHELXTL 6.14 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1e _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0876P)^2^+0.0000P] 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 0.8(12) _refine_ls_number_reflns 4277 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1322 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 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 0.5149(2) 0.51323(14) 0.85496(19) 0.0304(4) Uani 1 1 d . . . O2 O 0.4247(2) 0.46329(12) 0.63569(19) 0.0277(4) Uani 1 1 d . . . O3 O -0.1113(2) 0.54304(14) 0.42812(19) 0.0334(4) Uani 1 1 d . . . O4 O -0.2985(2) 0.60723(14) 0.5694(2) 0.0328(4) Uani 1 1 d . . . N2 N 0.3001(2) 0.58026(13) 1.0482(2) 0.0202(4) Uani 1 1 d . . . H2 H 0.3996 0.5578 1.0363 0.030 Uiso 1 1 calc R . . N1 N 0.5702(2) 0.64083(13) 1.2287(2) 0.0195(4) Uani 1 1 d . . . H1 H 0.6408 0.6073 1.1801 0.029 Uiso 1 1 calc R . . N3 N 0.4017(2) 0.50438(14) 0.7556(2) 0.0219(4) Uani 1 1 d . . . N4 N -0.1560(3) 0.57494(14) 0.5503(2) 0.0256(4) Uani 1 1 d . . . C2 C 0.2623(3) 0.61612(17) 1.1981(2) 0.0219(5) Uani 1 1 d . . . H2A H 0.1677 0.5824 1.2392 0.026 Uiso 1 1 calc R . . H2B H 0.2329 0.6819 1.1918 0.026 Uiso 1 1 calc R . . C1 C 0.4198(3) 0.60284(17) 1.3004(2) 0.0219(5) Uani 1 1 d . . . H1A H 0.4039 0.6341 1.3967 0.026 Uiso 1 1 calc R . . H1B H 0.4363 0.5367 1.3206 0.026 Uiso 1 1 calc R . . C9 C 0.5866(3) 0.74214(16) 1.2494(3) 0.0208(5) Uani 1 1 d . . . H9A H 0.6062 0.7555 1.3565 0.025 Uiso 1 1 calc R . . H9B H 0.4815 0.7720 1.2174 0.025 Uiso 1 1 calc R . . C10 C 0.7281(3) 0.78297(15) 1.1611(2) 0.0195(4) Uani 1 1 d . . . C11 C 0.7013(3) 0.80325(16) 1.0053(3) 0.0247(5) Uani 1 1 d . . . C12 C 0.5476(4) 0.78192(17) 0.9251(3) 0.0312(6) Uani 1 1 d . . . H12 H 0.4600 0.7535 0.9760 0.037 Uiso 1 1 calc R . . C13 C 0.5272(4) 0.8027(2) 0.7750(3) 0.0426(7) Uani 1 1 d . . . H13 H 0.4262 0.7878 0.7241 0.051 Uiso 1 1 calc R . . C14 C 0.6584(5) 0.8468(2) 0.6948(3) 0.0472(8) Uani 1 1 d . . . H14 H 0.6414 0.8616 0.5926 0.057 Uiso 1 1 calc R . . C15 C 0.8054(4) 0.86727(19) 0.7646(3) 0.0396(7) Uani 1 1 d . . . H15 H 0.8903 0.8954 0.7099 0.047 Uiso 1 1 calc R . . C16 C 0.8349(4) 0.84665(16) 0.9221(3) 0.0290(6) Uani 1 1 d . . . C17 C 0.9878(4) 0.86791(17) 0.9965(3) 0.0311(6) Uani 1 1 d . . . H17 H 1.0726 0.8966 0.9424 0.037 Uiso 1 1 calc R . . C18 C 1.0169(3) 0.84746(16) 1.1491(3) 0.0251(5) Uani 1 1 d . . . C19 C 1.1729(3) 0.87089(18) 1.2273(4) 0.0339(6) Uani 1 1 d . . . H19 H 1.2569 0.9011 1.1742 0.041 Uiso 1 1 calc R . . C20 C 1.2011(3) 0.85044(17) 1.3751(3) 0.0341(6) Uani 1 1 d . . . H20 H 1.3033 0.8665 1.4229 0.041 Uiso 1 1 calc R . . C21 C 1.0753(3) 0.80451(18) 1.4574(3) 0.0319(6) Uani 1 1 d . . . H21 H 1.0965 0.7890 1.5589 0.038 Uiso 1 1 calc R . . C22 C 0.9231(3) 0.78263(17) 1.3901(3) 0.0249(5) Uani 1 1 d . . . H22 H 0.8412 0.7538 1.4475 0.030 Uiso 1 1 calc R . . C23 C 0.8862(3) 0.80303(15) 1.2329(3) 0.0213(5) Uani 1 1 d . . . C3 C 0.1938(3) 0.57910(15) 0.9273(2) 0.0183(4) Uani 1 1 d . . . C4 C 0.2372(3) 0.54442(15) 0.7826(2) 0.0187(4) Uani 1 1 d . . . C5 C 0.1226(3) 0.54291(15) 0.6598(2) 0.0209(4) Uani 1 1 d . . . H5 H 0.1538 0.5190 0.5665 0.025 Uiso 1 1 calc R . . C6 C -0.0368(3) 0.57709(16) 0.6785(3) 0.0215(5) Uani 1 1 d . . . C7 C -0.0874(3) 0.61197(16) 0.8187(3) 0.0219(5) Uani 1 1 d . . . H7 H -0.1967 0.6343 0.8296 0.026 Uiso 1 1 calc R . . C8 C 0.0253(3) 0.61290(16) 0.9390(2) 0.0202(4) Uani 1 1 d . . . H8 H -0.0089 0.6363 1.0317 0.024 Uiso 1 1 calc R . . 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 0.0188(8) 0.0431(11) 0.0289(8) -0.0065(8) -0.0032(7) 0.0088(7) O2 0.0267(9) 0.0304(9) 0.0264(9) -0.0080(7) 0.0052(7) 0.0033(7) O3 0.0411(11) 0.0353(10) 0.0233(8) -0.0008(8) -0.0096(8) -0.0009(9) O4 0.0212(9) 0.0430(11) 0.0337(9) 0.0104(8) -0.0070(7) -0.0007(8) N2 0.0144(9) 0.0236(9) 0.0223(9) -0.0038(8) -0.0024(7) 0.0029(7) N1 0.0134(8) 0.0236(9) 0.0214(9) -0.0030(8) -0.0004(7) -0.0004(7) N3 0.0211(10) 0.0211(9) 0.0237(9) -0.0010(8) 0.0027(7) 0.0025(8) N4 0.0259(11) 0.0233(10) 0.0272(10) 0.0064(8) -0.0089(8) -0.0035(8) C2 0.0175(10) 0.0256(11) 0.0224(10) -0.0026(9) -0.0029(8) -0.0025(9) C1 0.0207(11) 0.0248(11) 0.0200(10) 0.0020(9) -0.0026(8) -0.0052(9) C9 0.0152(10) 0.0248(11) 0.0223(11) -0.0038(9) 0.0007(8) -0.0002(8) C10 0.0201(11) 0.0167(10) 0.0217(10) -0.0019(9) 0.0020(8) 0.0023(8) C11 0.0328(13) 0.0184(11) 0.0232(11) -0.0008(9) 0.0046(9) 0.0074(9) C12 0.0378(15) 0.0261(12) 0.0295(13) -0.0016(11) -0.0020(11) 0.0083(11) C13 0.063(2) 0.0325(15) 0.0311(13) -0.0041(11) -0.0124(13) 0.0140(13) C14 0.089(3) 0.0293(15) 0.0235(13) 0.0022(11) 0.0011(15) 0.0167(15) C15 0.069(2) 0.0233(12) 0.0274(13) 0.0034(11) 0.0165(13) 0.0115(13) C16 0.0418(16) 0.0165(11) 0.0294(13) -0.0010(9) 0.0122(11) 0.0074(10) C17 0.0352(14) 0.0191(11) 0.0403(13) 0.0009(11) 0.0210(11) -0.0005(10) C18 0.0211(12) 0.0154(10) 0.0395(14) -0.0040(9) 0.0105(10) 0.0011(8) C19 0.0180(12) 0.0212(11) 0.0631(18) -0.0074(13) 0.0138(12) -0.0045(10) C20 0.0159(12) 0.0282(13) 0.0579(18) -0.0165(12) -0.0037(11) 0.0019(9) C21 0.0266(14) 0.0277(13) 0.0410(14) -0.0062(11) -0.0050(11) 0.0031(10) C22 0.0211(12) 0.0237(11) 0.0299(12) -0.0003(10) 0.0006(9) 0.0025(9) C23 0.0190(11) 0.0161(10) 0.0293(11) -0.0023(8) 0.0071(9) 0.0024(8) C3 0.0172(10) 0.0150(9) 0.0225(10) -0.0007(9) -0.0029(8) 0.0002(8) C4 0.0156(10) 0.0161(9) 0.0244(10) 0.0002(9) -0.0003(8) 0.0018(8) C5 0.0254(11) 0.0180(10) 0.0192(10) 0.0016(9) -0.0002(8) -0.0020(9) C6 0.0220(11) 0.0184(10) 0.0237(10) 0.0022(9) -0.0048(9) -0.0035(9) C7 0.0161(10) 0.0188(10) 0.0305(11) 0.0000(10) -0.0049(9) -0.0005(9) C8 0.0166(10) 0.0208(10) 0.0230(10) -0.0040(9) -0.0005(8) 0.0009(9) _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 N3 1.240(2) . ? O2 N3 1.226(2) . ? O3 N4 1.230(3) . ? O4 N4 1.236(3) . ? N2 C3 1.337(3) . ? N2 C2 1.455(3) . ? N1 C9 1.465(3) . ? N1 C1 1.469(3) . ? N3 C4 1.449(3) . ? N4 C6 1.450(3) . ? C2 C1 1.528(3) . ? C9 C10 1.501(3) . ? C10 C11 1.411(3) . ? C10 C23 1.415(3) . ? C11 C12 1.422(4) . ? C11 C16 1.445(4) . ? C12 C13 1.359(4) . ? C13 C14 1.421(5) . ? C14 C15 1.333(5) . ? C15 C16 1.429(4) . ? C16 C17 1.393(4) . ? C17 C18 1.386(4) . ? C18 C19 1.436(4) . ? C18 C23 1.437(3) . ? C19 C20 1.345(4) . ? C20 C21 1.411(4) . ? C21 C22 1.364(3) . ? C22 C23 1.436(3) . ? C3 C4 1.418(3) . ? C3 C8 1.426(3) . ? C4 C5 1.390(3) . ? C5 C6 1.368(3) . ? C6 C7 1.400(3) . ? C7 C8 1.364(3) . ? 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 N2 C2 125.77(19) . . ? C9 N1 C1 112.48(18) . . ? O2 N3 O1 122.20(19) . . ? O2 N3 C4 119.19(18) . . ? O1 N3 C4 118.61(18) . . ? O3 N4 O4 123.06(19) . . ? O3 N4 C6 119.4(2) . . ? O4 N4 C6 117.6(2) . . ? N2 C2 C1 107.70(18) . . ? N1 C1 C2 111.09(18) . . ? N1 C9 C10 112.64(18) . . ? C11 C10 C23 119.9(2) . . ? C11 C10 C9 119.3(2) . . ? C23 C10 C9 120.80(19) . . ? C10 C11 C12 122.7(2) . . ? C10 C11 C16 119.3(2) . . ? C12 C11 C16 118.1(2) . . ? C13 C12 C11 120.7(3) . . ? C12 C13 C14 120.8(3) . . ? C15 C14 C13 120.7(3) . . ? C14 C15 C16 121.1(3) . . ? C17 C16 C15 121.7(3) . . ? C17 C16 C11 119.7(2) . . ? C15 C16 C11 118.6(3) . . ? C18 C17 C16 121.8(2) . . ? C17 C18 C19 122.1(2) . . ? C17 C18 C23 119.2(2) . . ? C19 C18 C23 118.7(2) . . ? C20 C19 C18 121.9(2) . . ? C19 C20 C21 119.9(2) . . ? C22 C21 C20 120.8(3) . . ? C21 C22 C23 121.6(2) . . ? C10 C23 C22 122.7(2) . . ? C10 C23 C18 120.1(2) . . ? C22 C23 C18 117.1(2) . . ? N2 C3 C4 123.7(2) . . ? N2 C3 C8 120.43(19) . . ? C4 C3 C8 115.84(18) . . ? C5 C4 C3 122.2(2) . . ? C5 C4 N3 115.9(2) . . ? C3 C4 N3 121.89(18) . . ? C6 C5 C4 119.0(2) . . ? C5 C6 C7 121.52(19) . . ? C5 C6 N4 118.7(2) . . ? C7 C6 N4 119.7(2) . . ? C8 C7 C6 119.3(2) . . ? C7 C8 C3 122.2(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 C3 N2 C2 C1 179.7(2) . . . . ? C9 N1 C1 C2 82.0(2) . . . . ? N2 C2 C1 N1 51.0(2) . . . . ? C1 N1 C9 C10 -173.20(17) . . . . ? N1 C9 C10 C11 81.7(2) . . . . ? N1 C9 C10 C23 -99.6(2) . . . . ? C23 C10 C11 C12 177.8(2) . . . . ? C9 C10 C11 C12 -3.5(3) . . . . ? C23 C10 C11 C16 -1.6(3) . . . . ? C9 C10 C11 C16 177.1(2) . . . . ? C10 C11 C12 C13 -180.0(2) . . . . ? C16 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C12 C13 C14 C15 1.3(4) . . . . ? C13 C14 C15 C16 -0.8(4) . . . . ? C14 C15 C16 C17 -179.8(2) . . . . ? C14 C15 C16 C11 -0.3(4) . . . . ? C10 C11 C16 C17 -0.1(3) . . . . ? C12 C11 C16 C17 -179.5(2) . . . . ? C10 C11 C16 C15 -179.6(2) . . . . ? C12 C11 C16 C15 0.9(3) . . . . ? C15 C16 C17 C18 -179.6(2) . . . . ? C11 C16 C17 C18 0.9(3) . . . . ? C16 C17 C18 C19 -178.7(2) . . . . ? C16 C17 C18 C23 0.1(3) . . . . ? C17 C18 C19 C20 -179.6(2) . . . . ? C23 C18 C19 C20 1.6(3) . . . . ? C18 C19 C20 C21 0.1(4) . . . . ? C19 C20 C21 C22 -1.8(4) . . . . ? C20 C21 C22 C23 1.6(4) . . . . ? C11 C10 C23 C22 -178.8(2) . . . . ? C9 C10 C23 C22 2.5(3) . . . . ? C11 C10 C23 C18 2.5(3) . . . . ? C9 C10 C23 C18 -176.13(19) . . . . ? C21 C22 C23 C10 -178.6(2) . . . . ? C21 C22 C23 C18 0.1(3) . . . . ? C17 C18 C23 C10 -1.8(3) . . . . ? C19 C18 C23 C10 177.0(2) . . . . ? C17 C18 C23 C22 179.5(2) . . . . ? C19 C18 C23 C22 -1.7(3) . . . . ? C2 N2 C3 C4 179.2(2) . . . . ? C2 N2 C3 C8 -1.6(3) . . . . ? N2 C3 C4 C5 179.0(2) . . . . ? C8 C3 C4 C5 -0.3(3) . . . . ? N2 C3 C4 N3 1.8(3) . . . . ? C8 C3 C4 N3 -177.45(19) . . . . ? O2 N3 C4 C5 -7.8(3) . . . . ? O1 N3 C4 C5 172.0(2) . . . . ? O2 N3 C4 C3 169.5(2) . . . . ? O1 N3 C4 C3 -10.7(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? N3 C4 C5 C6 178.1(2) . . . . ? C4 C5 C6 C7 -1.1(3) . . . . ? C4 C5 C6 N4 -179.7(2) . . . . ? O3 N4 C6 C5 -0.3(3) . . . . ? O4 N4 C6 C5 -179.2(2) . . . . ? O3 N4 C6 C7 -179.0(2) . . . . ? O4 N4 C6 C7 2.2(3) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? N4 C6 C7 C8 179.4(2) . . . . ? C6 C7 C8 C3 -0.2(3) . . . . ? N2 C3 C8 C7 -179.3(2) . . . . ? C4 C3 C8 C7 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.502 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.059 #===END data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 198 degree C _chemical_formula_moiety C29 H22 N6 O8.DMSO _chemical_formula_sum 'C31 H28 N6 O9 S' _chemical_formula_weight 660.65 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P -1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9560(5) _cell_length_b 12.6560(6) _cell_length_c 12.7730(2) _cell_angle_alpha 112.539(2) _cell_angle_beta 103.225(2) _cell_angle_gamma 101.278(6) _cell_volume 1511.34(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9660 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Enraf-Nonius CAD4 Mach2 _diffrn_measurement_method Theta-2Theta scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1h _diffrn_standards_decay_% <0.5% _diffrn_reflns_number 4185 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 22.48 _reflns_number_total 3934 _reflns_number_gt 2877 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4 Mach2 _computing_cell_refinement CAD4 _computing_data_reduction SHELXL-97 _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1 e _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1164P)^2^+0.0000P] 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 3934 _refine_ls_number_parameters 424 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1677 _refine_ls_wR_factor_gt 0.1477 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _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 S1A S 0.84303(10) 0.04630(10) 0.41766(9) 0.0651(4) Uani 1 1 d . . . O4 O 0.4180(3) -0.2114(3) 0.9178(3) 0.0918(10) Uani 1 1 d . . . O3 O 0.6067(3) -0.1537(3) 1.0552(3) 0.0744(8) Uani 1 1 d . . . O2 O 0.9846(2) 0.1196(2) 1.0523(2) 0.0593(7) Uani 1 1 d . . . O1 O 0.9731(2) 0.0755(2) 0.8688(2) 0.0577(7) Uani 1 1 d . . . O5 O 0.2181(3) 0.1172(3) 0.4293(3) 0.0804(9) Uani 1 1 d . . . O6 O 0.1634(3) 0.2067(3) 0.3230(3) 0.0937(11) Uani 1 1 d . . . O7 O 0.4737(3) 0.4504(4) 0.2427(3) 0.0948(11) Uani 1 1 d . . . O8 O 0.6717(3) 0.5411(3) 0.3705(3) 0.0790(9) Uani 1 1 d . . . O1A O 0.7030(3) 0.0132(3) 0.4125(2) 0.0707(8) Uani 1 1 d . . . N1 N 0.4637(3) 0.1965(2) 0.5802(2) 0.0480(7) Uani 1 1 d . . . H1 H 0.3899 0.1400 0.5521 0.072 Uiso 1 1 calc R . . N2 N 0.7398(2) 0.1551(2) 0.7854(2) 0.0357(6) Uani 1 1 d . . . N3 N 0.9220(3) 0.0860(2) 0.9462(3) 0.0438(7) Uani 1 1 d . . . N4 N 0.5357(4) -0.1551(3) 0.9649(3) 0.0602(9) Uani 1 1 d . . . N5 N 0.2474(3) 0.1895(3) 0.3902(3) 0.0572(8) Uani 1 1 d . . . N6 N 0.5621(4) 0.4648(3) 0.3297(3) 0.0627(9) Uani 1 1 d . . . C1A C 0.8659(5) -0.0858(4) 0.3247(4) 0.0877(14) Uani 1 1 d . . . H1AC H 0.8657 -0.1387 0.3621 0.132 Uiso 1 1 calc R . . H1BC H 0.9489 -0.0664 0.3123 0.132 Uiso 1 1 calc R . . H1CC H 0.7956 -0.1249 0.2487 0.132 Uiso 1 1 calc R . . C2A C 0.8500(4) 0.1188(5) 0.3247(5) 0.0936(16) Uani 1 1 d . . . H2AC H 0.8382 0.1961 0.3621 0.140 Uiso 1 1 calc R . . H2BC H 0.7813 0.0705 0.2482 0.140 Uiso 1 1 calc R . . H2CC H 0.9344 0.1294 0.3133 0.140 Uiso 1 1 calc R . . C1 C 0.5576(3) 0.2188(3) 0.6926(3) 0.0432(8) Uani 1 1 d . . . H1A H 0.5099 0.1949 0.7394 0.052 Uiso 1 1 calc R . . H1B H 0.6043 0.3045 0.7383 0.052 Uiso 1 1 calc R . . C2 C 0.6577(3) 0.1510(3) 0.6746(3) 0.0407(8) Uani 1 1 d . . . H2A H 0.6107 0.0674 0.6173 0.049 Uiso 1 1 calc R . . H2B H 0.7150 0.1848 0.6399 0.049 Uiso 1 1 calc R . . C3 C 0.6973(3) 0.0697(3) 0.8198(3) 0.0365(7) Uani 1 1 d . . . C8 C 0.5625(3) -0.0016(3) 0.7713(3) 0.0449(8) Uani 1 1 d . . . H8 H 0.5067 0.0019 0.7067 0.054 Uiso 1 1 calc R . . C7 C 0.5123(3) -0.0751(3) 0.8165(3) 0.0492(9) Uani 1 1 d . . . H7 H 0.4233 -0.1205 0.7827 0.059 Uiso 1 1 calc R . . C6 C 0.5930(3) -0.0826(3) 0.9126(3) 0.0449(8) Uani 1 1 d . . . C5 C 0.7261(3) -0.0237(3) 0.9577(3) 0.0414(8) Uani 1 1 d . . . H5 H 0.7806 -0.0314 1.0199 0.050 Uiso 1 1 calc R . . C4 C 0.7781(3) 0.0475(3) 0.9092(3) 0.0372(7) Uani 1 1 d . . . C9 C 0.8668(3) 0.2537(3) 0.8558(3) 0.0399(8) Uani 1 1 d . . . H9A H 0.9339 0.2300 0.8227 0.048 Uiso 1 1 calc R . . H9B H 0.8927 0.2644 0.9380 0.048 Uiso 1 1 calc R . . C10 C 0.8631(3) 0.3733(3) 0.8573(3) 0.0351(7) Uani 1 1 d . . . C11 C 0.9221(3) 0.4150(3) 0.7870(3) 0.0382(8) Uani 1 1 d . . . C12 C 0.9803(3) 0.3489(3) 0.7069(3) 0.0532(9) Uani 1 1 d . . . H12 H 0.9795 0.2722 0.6978 0.064 Uiso 1 1 calc R . . C13 C 1.0372(4) 0.3942(4) 0.6430(4) 0.0717(12) Uani 1 1 d . . . H13 H 1.0738 0.3480 0.5906 0.086 Uiso 1 1 calc R . . C14 C 1.0416(4) 0.5101(5) 0.6552(4) 0.0758(13) Uani 1 1 d . . . H14 H 1.0835 0.5413 0.6129 0.091 Uiso 1 1 calc R . . C15 C 0.9857(4) 0.5754(4) 0.7273(4) 0.0621(11) Uani 1 1 d . . . H15 H 0.9872 0.6511 0.7328 0.074 Uiso 1 1 calc R . . C16 C 0.9239(3) 0.5322(3) 0.7961(3) 0.0431(8) Uani 1 1 d . . . C17 C 0.8645(3) 0.5984(3) 0.8696(3) 0.0473(9) Uani 1 1 d . . . H17 H 0.8637 0.6729 0.8729 0.057 Uiso 1 1 calc R . . C18 C 0.8056(3) 0.5586(3) 0.9392(3) 0.0432(8) Uani 1 1 d . . . C19 C 0.7441(4) 0.6279(3) 1.0137(3) 0.0605(10) Uani 1 1 d . . . H19 H 0.7452 0.7034 1.0187 0.073 Uiso 1 1 calc R . . C20 C 0.6839(4) 0.5855(4) 1.0777(4) 0.0731(12) Uani 1 1 d . . . H20 H 0.6432 0.6314 1.1257 0.088 Uiso 1 1 calc R . . C21 C 0.6831(4) 0.4731(4) 1.0711(3) 0.0657(11) Uani 1 1 d . . . H21 H 0.6416 0.4449 1.1155 0.079 Uiso 1 1 calc R . . C22 C 0.7404(3) 0.4041(3) 1.0028(3) 0.0481(9) Uani 1 1 d . . . H22 H 0.7382 0.3296 1.0012 0.058 Uiso 1 1 calc R . . C23 C 0.8049(3) 0.4428(3) 0.9324(3) 0.0375(7) Uani 1 1 d . . . C24 C 0.4837(3) 0.2579(3) 0.5168(3) 0.0426(8) Uani 1 1 d . . . C25 C 0.3847(3) 0.2554(3) 0.4222(3) 0.0431(8) Uani 1 1 d . . . C26 C 0.4111(3) 0.3209(3) 0.3609(3) 0.0472(9) Uani 1 1 d . . . H26 H 0.3435 0.3163 0.2984 0.057 Uiso 1 1 calc R . . C27 C 0.5363(3) 0.3925(3) 0.3918(3) 0.0481(9) Uani 1 1 d . . . C28 C 0.6371(3) 0.4019(3) 0.4860(3) 0.0550(9) Uani 1 1 d . . . H28 H 0.7221 0.4523 0.5075 0.066 Uiso 1 1 calc R . . C29 C 0.6120(3) 0.3376(3) 0.5472(3) 0.0534(9) Uani 1 1 d . . . H29 H 0.6807 0.3457 0.6109 0.064 Uiso 1 1 calc R . . 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 S1A 0.0489(6) 0.0742(7) 0.0574(6) 0.0222(5) 0.0093(5) 0.0137(5) O4 0.067(2) 0.086(2) 0.141(3) 0.075(2) 0.042(2) 0.0067(17) O3 0.092(2) 0.078(2) 0.097(2) 0.0657(18) 0.0496(19) 0.0399(17) O2 0.0547(16) 0.0476(15) 0.0646(17) 0.0331(13) -0.0065(13) 0.0078(12) O1 0.0483(15) 0.0653(17) 0.0851(18) 0.0495(15) 0.0313(14) 0.0274(13) O5 0.0494(17) 0.097(2) 0.090(2) 0.0625(19) -0.0022(15) -0.0014(15) O6 0.0437(17) 0.120(3) 0.121(3) 0.081(2) -0.0051(17) 0.0161(16) O7 0.076(2) 0.163(3) 0.086(2) 0.093(2) 0.0290(18) 0.043(2) O8 0.071(2) 0.100(2) 0.094(2) 0.0645(19) 0.0391(17) 0.0262(18) O1A 0.0555(16) 0.091(2) 0.0803(19) 0.0449(16) 0.0337(14) 0.0271(14) N1 0.0408(16) 0.0454(16) 0.0506(17) 0.0254(14) -0.0002(13) 0.0088(13) N2 0.0363(14) 0.0298(14) 0.0398(14) 0.0193(12) 0.0058(12) 0.0083(11) N3 0.0421(17) 0.0325(15) 0.062(2) 0.0293(14) 0.0102(16) 0.0130(13) N4 0.070(2) 0.0485(19) 0.095(3) 0.0465(19) 0.050(2) 0.0287(18) N5 0.0407(18) 0.066(2) 0.0557(19) 0.0283(17) 0.0024(15) 0.0131(15) N6 0.064(2) 0.089(3) 0.063(2) 0.047(2) 0.0350(19) 0.040(2) C1A 0.088(3) 0.106(4) 0.077(3) 0.036(3) 0.034(3) 0.050(3) C2A 0.059(3) 0.117(4) 0.122(4) 0.075(4) 0.034(3) 0.017(3) C1 0.045(2) 0.0385(18) 0.0401(18) 0.0186(15) 0.0039(15) 0.0123(15) C2 0.0442(19) 0.0380(18) 0.0379(18) 0.0185(15) 0.0092(15) 0.0111(15) C3 0.0395(18) 0.0298(17) 0.0403(17) 0.0153(14) 0.0126(15) 0.0132(14) C8 0.0409(19) 0.0383(18) 0.053(2) 0.0227(16) 0.0062(16) 0.0133(15) C7 0.039(2) 0.0369(19) 0.073(2) 0.0255(18) 0.0201(18) 0.0110(15) C6 0.050(2) 0.0355(18) 0.064(2) 0.0300(17) 0.0275(18) 0.0185(16) C5 0.049(2) 0.0358(18) 0.0468(19) 0.0228(16) 0.0171(16) 0.0192(16) C4 0.0342(18) 0.0333(17) 0.0480(18) 0.0222(15) 0.0117(15) 0.0129(14) C9 0.0376(18) 0.0388(18) 0.0446(18) 0.0238(15) 0.0083(15) 0.0106(14) C10 0.0287(16) 0.0325(17) 0.0422(17) 0.0209(14) 0.0043(14) 0.0062(13) C11 0.0293(17) 0.0404(18) 0.0428(18) 0.0230(15) 0.0049(15) 0.0058(14) C12 0.045(2) 0.057(2) 0.062(2) 0.031(2) 0.0195(19) 0.0134(17) C13 0.059(3) 0.087(3) 0.071(3) 0.034(2) 0.033(2) 0.015(2) C14 0.067(3) 0.096(4) 0.075(3) 0.056(3) 0.029(2) 0.005(3) C15 0.054(2) 0.068(3) 0.072(3) 0.051(2) 0.013(2) 0.004(2) C16 0.0371(18) 0.0416(19) 0.0499(19) 0.0289(17) 0.0060(16) 0.0038(15) C17 0.044(2) 0.0321(18) 0.057(2) 0.0243(17) -0.0015(17) 0.0051(15) C18 0.0379(19) 0.0341(18) 0.0460(19) 0.0159(16) 0.0022(16) 0.0056(15) C19 0.060(2) 0.042(2) 0.065(2) 0.0115(19) 0.014(2) 0.0191(19) C20 0.071(3) 0.063(3) 0.067(3) 0.007(2) 0.031(2) 0.022(2) C21 0.068(3) 0.061(3) 0.057(2) 0.018(2) 0.030(2) 0.005(2) C22 0.053(2) 0.042(2) 0.0431(19) 0.0176(16) 0.0155(17) 0.0058(16) C23 0.0332(17) 0.0349(17) 0.0396(17) 0.0185(14) 0.0059(14) 0.0048(14) C24 0.040(2) 0.0404(19) 0.0421(18) 0.0165(16) 0.0052(15) 0.0154(15) C25 0.0362(19) 0.048(2) 0.0384(18) 0.0156(16) 0.0056(15) 0.0155(15) C26 0.046(2) 0.060(2) 0.0368(18) 0.0209(17) 0.0096(16) 0.0272(18) C27 0.050(2) 0.062(2) 0.047(2) 0.0317(18) 0.0206(18) 0.0281(18) C28 0.040(2) 0.058(2) 0.067(2) 0.032(2) 0.0118(18) 0.0160(17) C29 0.040(2) 0.062(2) 0.058(2) 0.036(2) 0.0025(17) 0.0129(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 S1A O1A 1.488(3) . ? S1A C1A 1.745(5) . ? S1A C2A 1.763(5) . ? O4 N4 1.221(4) . ? O3 N4 1.227(4) . ? O2 N3 1.228(3) . ? O1 N3 1.221(3) . ? O5 N5 1.224(4) . ? O6 N5 1.221(4) . ? O7 N6 1.220(4) . ? O8 N6 1.232(4) . ? N1 C24 1.344(4) . ? N1 C1 1.449(4) . ? N2 C3 1.356(4) . ? N2 C2 1.469(4) . ? N2 C9 1.480(4) . ? N3 C4 1.459(4) . ? N4 C6 1.455(4) . ? N5 C25 1.446(4) . ? N6 C27 1.451(5) . ? C1 C2 1.524(4) . ? C3 C8 1.418(4) . ? C3 C4 1.430(4) . ? C8 C7 1.364(5) . ? C7 C6 1.387(5) . ? C6 C5 1.369(4) . ? C5 C4 1.381(4) . ? C9 C10 1.515(4) . ? C10 C23 1.398(4) . ? C10 C11 1.413(4) . ? C11 C12 1.416(5) . ? C11 C16 1.439(4) . ? C12 C13 1.354(5) . ? C13 C14 1.405(6) . ? C14 C15 1.334(6) . ? C15 C16 1.424(5) . ? C16 C17 1.377(5) . ? C17 C18 1.392(5) . ? C18 C19 1.419(5) . ? C18 C23 1.432(4) . ? C19 C20 1.354(6) . ? C20 C21 1.392(6) . ? C21 C22 1.342(5) . ? C22 C23 1.429(4) . ? C24 C25 1.412(4) . ? C24 C29 1.428(5) . ? C25 C26 1.377(5) . ? C26 C27 1.360(5) . ? C27 C28 1.383(5) . ? C28 C29 1.359(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 O1A S1A C1A 106.4(2) . . ? O1A S1A C2A 106.04(19) . . ? C1A S1A C2A 97.1(3) . . ? C24 N1 C1 124.7(3) . . ? C3 N2 C2 119.5(2) . . ? C3 N2 C9 122.4(2) . . ? C2 N2 C9 118.1(2) . . ? O1 N3 O2 123.6(3) . . ? O1 N3 C4 118.3(3) . . ? O2 N3 C4 117.9(3) . . ? O4 N4 O3 123.7(3) . . ? O4 N4 C6 117.7(4) . . ? O3 N4 C6 118.6(3) . . ? O6 N5 O5 121.6(3) . . ? O6 N5 C25 118.6(3) . . ? O5 N5 C25 119.7(3) . . ? O7 N6 O8 123.2(3) . . ? O7 N6 C27 118.8(4) . . ? O8 N6 C27 117.9(3) . . ? N1 C1 C2 112.9(3) . . ? N2 C2 C1 114.2(2) . . ? N2 C3 C8 120.4(3) . . ? N2 C3 C4 124.8(3) . . ? C8 C3 C4 114.6(3) . . ? C7 C8 C3 122.0(3) . . ? C8 C7 C6 120.4(3) . . ? C5 C6 C7 120.6(3) . . ? C5 C6 N4 119.8(3) . . ? C7 C6 N4 119.6(3) . . ? C6 C5 C4 119.0(3) . . ? C5 C4 C3 122.6(3) . . ? C5 C4 N3 114.2(3) . . ? C3 C4 N3 122.8(3) . . ? N2 C9 C10 114.2(2) . . ? C23 C10 C11 121.0(3) . . ? C23 C10 C9 118.8(3) . . ? C11 C10 C9 120.1(3) . . ? C10 C11 C12 124.4(3) . . ? C10 C11 C16 118.6(3) . . ? C12 C11 C16 116.9(3) . . ? C13 C12 C11 121.9(4) . . ? C12 C13 C14 120.7(4) . . ? C15 C14 C13 120.1(4) . . ? C14 C15 C16 121.7(4) . . ? C17 C16 C15 122.1(3) . . ? C17 C16 C11 119.2(3) . . ? C15 C16 C11 118.7(3) . . ? C16 C17 C18 122.9(3) . . ? C17 C18 C19 122.0(3) . . ? C17 C18 C23 118.4(3) . . ? C19 C18 C23 119.6(3) . . ? C20 C19 C18 120.8(4) . . ? C19 C20 C21 119.7(4) . . ? C22 C21 C20 122.0(4) . . ? C21 C22 C23 121.2(3) . . ? C10 C23 C22 123.6(3) . . ? C10 C23 C18 119.8(3) . . ? C22 C23 C18 116.6(3) . . ? N1 C24 C25 125.1(3) . . ? N1 C24 C29 120.0(3) . . ? C25 C24 C29 114.9(3) . . ? C26 C25 C24 122.5(3) . . ? C26 C25 N5 116.2(3) . . ? C24 C25 N5 121.2(3) . . ? C27 C26 C25 119.8(3) . . ? C26 C27 C28 120.6(3) . . ? C26 C27 N6 119.4(3) . . ? C28 C27 N6 119.9(3) . . ? C29 C28 C27 120.0(3) . . ? C28 C29 C24 122.1(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 C24 N1 C1 C2 -86.3(4) . . . . ? C3 N2 C2 C1 88.8(3) . . . . ? C9 N2 C2 C1 -91.0(3) . . . . ? N1 C1 C2 N2 -170.2(2) . . . . ? C2 N2 C3 C8 -17.7(4) . . . . ? C9 N2 C3 C8 162.1(3) . . . . ? C2 N2 C3 C4 165.8(3) . . . . ? C9 N2 C3 C4 -14.4(4) . . . . ? N2 C3 C8 C7 -169.9(3) . . . . ? C4 C3 C8 C7 7.0(4) . . . . ? C3 C8 C7 C6 -0.1(5) . . . . ? C8 C7 C6 C5 -5.0(5) . . . . ? C8 C7 C6 N4 175.8(3) . . . . ? O4 N4 C6 C5 -176.1(3) . . . . ? O3 N4 C6 C5 6.0(5) . . . . ? O4 N4 C6 C7 3.1(5) . . . . ? O3 N4 C6 C7 -174.8(3) . . . . ? C7 C6 C5 C4 2.7(5) . . . . ? N4 C6 C5 C4 -178.1(3) . . . . ? C6 C5 C4 C3 4.8(5) . . . . ? C6 C5 C4 N3 -168.2(3) . . . . ? N2 C3 C4 C5 167.3(3) . . . . ? C8 C3 C4 C5 -9.4(4) . . . . ? N2 C3 C4 N3 -20.3(5) . . . . ? C8 C3 C4 N3 163.1(3) . . . . ? O1 N3 C4 C5 132.7(3) . . . . ? O2 N3 C4 C5 -42.6(4) . . . . ? O1 N3 C4 C3 -40.3(4) . . . . ? O2 N3 C4 C3 144.4(3) . . . . ? C3 N2 C9 C10 -143.4(3) . . . . ? C2 N2 C9 C10 36.5(4) . . . . ? N2 C9 C10 C23 77.6(4) . . . . ? N2 C9 C10 C11 -104.7(3) . . . . ? C23 C10 C11 C12 -178.5(3) . . . . ? C9 C10 C11 C12 3.8(5) . . . . ? C23 C10 C11 C16 1.4(4) . . . . ? C9 C10 C11 C16 -176.3(3) . . . . ? C10 C11 C12 C13 -179.0(3) . . . . ? C16 C11 C12 C13 1.1(5) . . . . ? C11 C12 C13 C14 0.6(6) . . . . ? C12 C13 C14 C15 -2.1(7) . . . . ? C13 C14 C15 C16 1.8(6) . . . . ? C14 C15 C16 C17 -179.2(4) . . . . ? C14 C15 C16 C11 0.0(5) . . . . ? C10 C11 C16 C17 -2.1(4) . . . . ? C12 C11 C16 C17 177.8(3) . . . . ? C10 C11 C16 C15 178.7(3) . . . . ? C12 C11 C16 C15 -1.4(4) . . . . ? C15 C16 C17 C18 -178.8(3) . . . . ? C11 C16 C17 C18 2.0(5) . . . . ? C16 C17 C18 C19 -179.5(3) . . . . ? C16 C17 C18 C23 -1.1(5) . . . . ? C17 C18 C19 C20 177.9(3) . . . . ? C23 C18 C19 C20 -0.6(5) . . . . ? C18 C19 C20 C21 0.6(6) . . . . ? C19 C20 C21 C22 -0.1(6) . . . . ? C20 C21 C22 C23 -0.3(6) . . . . ? C11 C10 C23 C22 178.1(3) . . . . ? C9 C10 C23 C22 -4.2(4) . . . . ? C11 C10 C23 C18 -0.5(4) . . . . ? C9 C10 C23 C18 177.2(3) . . . . ? C21 C22 C23 C10 -178.3(3) . . . . ? C21 C22 C23 C18 0.3(5) . . . . ? C17 C18 C23 C10 0.3(4) . . . . ? C19 C18 C23 C10 178.8(3) . . . . ? C17 C18 C23 C22 -178.4(3) . . . . ? C19 C18 C23 C22 0.1(4) . . . . ? C1 N1 C24 C25 -165.8(3) . . . . ? C1 N1 C24 C29 11.1(5) . . . . ? N1 C24 C25 C26 179.6(3) . . . . ? C29 C24 C25 C26 2.6(5) . . . . ? N1 C24 C25 N5 3.9(5) . . . . ? C29 C24 C25 N5 -173.1(3) . . . . ? O6 N5 C25 C26 -8.6(5) . . . . ? O5 N5 C25 C26 170.6(3) . . . . ? O6 N5 C25 C24 167.4(3) . . . . ? O5 N5 C25 C24 -13.5(5) . . . . ? C24 C25 C26 C27 -0.7(5) . . . . ? N5 C25 C26 C27 175.1(3) . . . . ? C25 C26 C27 C28 -1.2(5) . . . . ? C25 C26 C27 N6 -177.6(3) . . . . ? O7 N6 C27 C26 -7.6(5) . . . . ? O8 N6 C27 C26 170.0(3) . . . . ? O7 N6 C27 C28 176.0(3) . . . . ? O8 N6 C27 C28 -6.4(5) . . . . ? C26 C27 C28 C29 1.2(5) . . . . ? N6 C27 C28 C29 177.6(3) . . . . ? C27 C28 C29 C24 0.8(6) . . . . ? N1 C24 C29 C28 -179.8(3) . . . . ? C25 C24 C29 C28 -2.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.254 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.076 #===END data_5H _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C10 H14 N4 O4.[H Cl O4] _chemical_formula_sum 'C10 H15 Cl N4 O8' _chemical_formula_weight 354.71 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P c a 21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 13.687(3) _cell_length_b 6.130(2) _cell_length_c 17.228(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1445.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28 _cell_measurement_theta_max +28 _exptl_crystal_description Pale yellow _exptl_crystal_colour Blocks _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9542 _exptl_absorpt_correction_T_max 0.9691 _exptl_absorpt_process_details SADABS 2.1 (BRUKER, 2003) _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CCD area detector (BRUKER SMART APEX) _diffrn_measurement_method w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <0.05 _diffrn_reflns_number 8899 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3541 _reflns_number_gt 3450 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART 5.628 (BRUKER, 2003) _computing_cell_refinement SAINT 6.45 (BRUKER, 2003) _computing_data_reduction SAINT 6.45 (BRUKER, 2003) _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics DIAMOND 2.1 e _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0895P)^2^+1.0252P] 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 0.03(4) _refine_ls_number_reflns 3541 _refine_ls_number_parameters 212 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 Cl1 Cl 0.54398(2) 1.45092(5) 0.61293(2) 0.01512(9) Uani 1 1 d . . . O1 O 0.55769(9) 0.9212(2) 0.74613(8) 0.0195(3) Uani 1 1 d . . . O2 O 0.62808(8) 1.1422(2) 0.82631(7) 0.0174(2) Uani 1 1 d . . . O3 O 0.48008(9) 1.7951(2) 0.90762(7) 0.0206(2) Uani 1 1 d . . . O4 O 0.32267(10) 1.8149(2) 0.91344(9) 0.0268(3) Uani 1 1 d . . . O5 O 0.52928(9) 1.2210(2) 0.59715(9) 0.0259(3) Uani 1 1 d . . . O6 O 0.45325(9) 1.5380(2) 0.64319(9) 0.0255(3) Uani 1 1 d . . . O7 O 0.56976(11) 1.5632(2) 0.54266(9) 0.0290(3) Uani 1 1 d . . . O8 O 0.62014(10) 1.4747(2) 0.66975(9) 0.0286(3) Uani 1 1 d . . . N1 N 0.33426(10) 1.0966(2) 0.55397(8) 0.0142(2) Uani 1 1 d . . . N1H1 H 0.3820(19) 1.148(4) 0.5840(14) 0.028(6) Uiso 1 1 d . . . N2 N 0.37107(10) 0.9642(2) 0.71353(8) 0.0137(3) Uani 1 1 d . . . H2 H 0.4230 0.8880 0.7063 0.016 Uiso 1 1 calc R . . N3 N 0.39821(10) 1.7232(2) 0.89391(8) 0.0168(3) Uani 1 1 d . . . N4 N 0.55557(9) 1.0827(2) 0.78884(8) 0.0136(2) Uani 1 1 d . . . C1 C 0.30263(13) 1.2617(3) 0.49509(11) 0.0225(3) Uani 1 1 d . . . H1A H 0.3563 1.2947 0.4612 0.034 Uiso 1 1 calc R . . H1B H 0.2820 1.3923 0.5211 0.034 Uiso 1 1 calc R . . H1C H 0.2493 1.2040 0.4653 0.034 Uiso 1 1 calc R . . C2 C 0.37646(12) 0.9003(3) 0.51516(10) 0.0174(3) Uani 1 1 d . . . H2A H 0.4291 0.9441 0.4818 0.026 Uiso 1 1 calc R . . H2B H 0.3268 0.8294 0.4850 0.026 Uiso 1 1 calc R . . H2C H 0.4006 0.8012 0.5538 0.026 Uiso 1 1 calc R . . C3 C 0.25117(10) 1.0430(2) 0.60777(10) 0.0158(3) Uani 1 1 d . . . H3A H 0.1996 0.9726 0.5784 0.019 Uiso 1 1 calc R . . H3B H 0.2250 1.1774 0.6290 0.019 Uiso 1 1 calc R . . C4 C 0.28192(10) 0.8941(3) 0.67426(9) 0.0135(3) Uani 1 1 d . . . H4A H 0.2293 0.8876 0.7119 0.016 Uiso 1 1 calc R . . H4B H 0.2917 0.7480 0.6541 0.016 Uiso 1 1 calc R . . C5 C 0.37766(11) 1.1398(2) 0.76021(8) 0.0127(3) Uani 1 1 d . . . C6 C 0.29395(11) 1.2713(3) 0.77571(9) 0.0137(3) Uani 1 1 d . . . H6 H 0.2337 1.2298 0.7555 0.016 Uiso 1 1 calc R . . C7 C 0.29988(11) 1.4577(2) 0.81962(10) 0.0147(3) Uani 1 1 d . . . H7 H 0.2443 1.5412 0.8288 0.018 Uiso 1 1 calc R . . C8 C 0.39034(12) 1.5212(3) 0.85049(9) 0.0142(3) Uani 1 1 d . . . C9 C 0.47268(11) 1.3971(3) 0.83965(9) 0.0135(3) Uani 1 1 d . . . H9 H 0.5320 1.4399 0.8612 0.016 Uiso 1 1 calc R . . C10 C 0.46646(11) 1.2073(3) 0.79623(9) 0.0133(3) 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 Cl1 0.01100(15) 0.01430(16) 0.02006(17) 0.00102(13) -0.00023(13) 0.00018(11) O1 0.0147(5) 0.0225(6) 0.0214(6) -0.0078(5) -0.0020(4) 0.0048(5) O2 0.0103(5) 0.0234(6) 0.0186(5) -0.0020(5) -0.0029(4) 0.0010(4) O3 0.0202(5) 0.0193(6) 0.0224(6) -0.0026(5) -0.0024(5) -0.0030(5) O4 0.0200(6) 0.0252(7) 0.0350(7) -0.0132(6) -0.0004(5) 0.0062(5) O5 0.0211(6) 0.0154(6) 0.0413(9) -0.0031(5) -0.0025(5) -0.0043(4) O6 0.0181(6) 0.0310(8) 0.0274(6) 0.0075(5) 0.0051(5) 0.0102(5) O7 0.0295(7) 0.0298(7) 0.0277(7) 0.0067(6) 0.0107(6) -0.0017(6) O8 0.0213(6) 0.0249(7) 0.0395(8) -0.0045(6) -0.0132(6) 0.0020(5) N1 0.0121(6) 0.0148(6) 0.0158(6) 0.0016(5) -0.0017(5) -0.0004(5) N2 0.0096(6) 0.0154(7) 0.0163(6) -0.0016(5) -0.0007(5) 0.0003(4) N3 0.0190(6) 0.0146(6) 0.0167(6) -0.0008(5) -0.0007(5) 0.0011(5) N4 0.0116(6) 0.0163(6) 0.0130(6) 0.0010(5) 0.0003(4) 0.0006(5) C1 0.0218(8) 0.0195(7) 0.0263(8) 0.0094(6) -0.0001(7) 0.0045(6) C2 0.0200(7) 0.0178(7) 0.0146(7) 0.0006(6) 0.0030(6) 0.0037(6) C3 0.0099(6) 0.0207(7) 0.0170(7) 0.0001(6) -0.0005(6) -0.0005(5) C4 0.0103(6) 0.0159(7) 0.0145(7) -0.0005(5) 0.0004(5) -0.0034(5) C5 0.0128(7) 0.0137(7) 0.0115(6) 0.0015(5) 0.0006(5) -0.0014(5) C6 0.0100(6) 0.0166(7) 0.0145(7) 0.0000(5) -0.0006(5) -0.0013(5) C7 0.0117(7) 0.0152(7) 0.0172(7) 0.0008(5) 0.0009(5) 0.0026(5) C8 0.0170(7) 0.0123(6) 0.0132(6) 0.0005(5) 0.0005(5) -0.0008(6) C9 0.0124(6) 0.0151(7) 0.0131(7) 0.0007(6) -0.0012(5) -0.0022(6) C10 0.0115(6) 0.0159(7) 0.0126(6) 0.0001(5) 0.0011(5) 0.0021(5) _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 Cl1 O7 1.4365(14) . ? Cl1 O8 1.4374(14) . ? Cl1 O6 1.4488(13) . ? Cl1 O5 1.4494(13) . ? O1 N4 1.2339(19) . ? O2 N4 1.2387(17) . ? O3 N3 1.2272(19) . ? O4 N3 1.224(2) . ? N1 C2 1.493(2) . ? N1 C1 1.497(2) . ? N1 C3 1.503(2) . ? N2 C5 1.3464(19) . ? N2 C4 1.4599(19) . ? N3 C8 1.450(2) . ? N4 C10 1.4447(19) . ? C3 C4 1.524(2) . ? C5 C10 1.426(2) . ? C5 C6 1.426(2) . ? C6 C7 1.372(2) . ? C7 C8 1.403(2) . ? C8 C9 1.373(2) . ? C9 C10 1.386(2) . ? 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 O7 Cl1 O8 110.32(9) . . ? O7 Cl1 O6 109.72(8) . . ? O8 Cl1 O6 109.82(9) . . ? O7 Cl1 O5 110.00(9) . . ? O8 Cl1 O5 109.10(8) . . ? O6 Cl1 O5 107.85(8) . . ? C2 N1 C1 110.70(13) . . ? C2 N1 C3 113.13(12) . . ? C1 N1 C3 110.28(12) . . ? C5 N2 C4 124.61(13) . . ? O4 N3 O3 123.58(14) . . ? O4 N3 C8 118.11(14) . . ? O3 N3 C8 118.29(14) . . ? O1 N4 O2 121.87(13) . . ? O1 N4 C10 119.77(13) . . ? O2 N4 C10 118.36(14) . . ? N1 C3 C4 112.66(11) . . ? N2 C4 C3 113.76(12) . . ? N2 C5 C10 123.31(14) . . ? N2 C5 C6 120.66(14) . . ? C10 C5 C6 116.03(13) . . ? C7 C6 C5 121.75(14) . . ? C6 C7 C8 119.50(14) . . ? C9 C8 C7 121.27(14) . . ? C9 C8 N3 118.84(14) . . ? C7 C8 N3 119.88(14) . . ? C8 C9 C10 119.24(14) . . ? C9 C10 C5 122.08(14) . . ? C9 C10 N4 116.07(14) . . ? C5 C10 N4 121.84(14) . . ? 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 C2 N1 C3 C4 61.55(17) . . . . ? C1 N1 C3 C4 -173.87(13) . . . . ? C5 N2 C4 C3 71.41(18) . . . . ? N1 C3 C4 N2 47.91(17) . . . . ? C4 N2 C5 C10 -178.36(14) . . . . ? C4 N2 C5 C6 1.0(2) . . . . ? N2 C5 C6 C7 -176.39(14) . . . . ? C10 C5 C6 C7 3.1(2) . . . . ? C5 C6 C7 C8 -0.2(2) . . . . ? C6 C7 C8 C9 -2.0(2) . . . . ? C6 C7 C8 N3 177.13(14) . . . . ? O4 N3 C8 C9 -168.93(15) . . . . ? O3 N3 C8 C9 12.6(2) . . . . ? O4 N3 C8 C7 11.9(2) . . . . ? O3 N3 C8 C7 -166.58(14) . . . . ? C7 C8 C9 C10 1.1(2) . . . . ? N3 C8 C9 C10 -178.05(13) . . . . ? C8 C9 C10 C5 2.0(2) . . . . ? C8 C9 C10 N4 -178.63(14) . . . . ? N2 C5 C10 C9 175.43(14) . . . . ? C6 C5 C10 C9 -4.0(2) . . . . ? N2 C5 C10 N4 -3.9(2) . . . . ? C6 C5 C10 N4 176.68(13) . . . . ? O1 N4 C10 C9 -174.34(14) . . . . ? O2 N4 C10 C9 5.9(2) . . . . ? O1 N4 C10 C5 5.0(2) . . . . ? O2 N4 C10 C5 -174.72(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.388 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.054 ### END