# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email gangli@zzu.edu.cn _publ_contact_author_name 'Dr Gang Li' _publ_section_title ; Design and construction of six metal-organic frameworks with 2-p-methoxyphenyl-1H-imidazole-4,5-dicarboxylate; ; loop_ _publ_author_name 'Xinjiang Cao' 'Jun Zhang' 'Chengjie Wang' 'Yanyan Zhu' 'Gang Li' # Attachment '- 1.cif' data_a #TrackingRef '- 1.cif' _database_code_depnum_ccdc_archive 'CCDC 854847' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cu N2 O6' _chemical_formula_weight 341.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.667(2) _cell_length_b 8.3608(16) _cell_length_c 12.363(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.224(2) _cell_angle_gamma 90.00 _cell_volume 1204.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 102 _cell_measurement_theta_min 3.483 _cell_measurement_theta_max 23.486 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7090 _exptl_absorpt_correction_T_max 0.7090 _exptl_absorpt_process_details SADABS(2009) _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4406 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2067 _reflns_number_gt 1974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; 'The DFIX restraint was applied in the refinement of the distance of H6E-O6 and H6F-O6 bonds in an appropriate region' 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^)+(0.0310P)^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 constr _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 0.013(15) _refine_ls_number_reflns 2067 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _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 Cu1 Cu 0.13538(4) 0.47619(4) 0.45844(4) 0.02074(13) Uani 1 1 d . . . N1 N 0.1292(4) 0.4830(4) 0.6174(4) 0.0174(9) Uani 1 1 d . . . N2 N 0.1213(4) 0.5168(4) 0.7965(4) 0.0177(10) Uani 1 1 d . . . O1 O 0.0469(3) 0.2399(3) 0.4886(2) 0.0321(7) Uani 1 1 d . . . O2 O -0.0144(3) 0.1004(4) 0.6260(2) 0.0322(7) Uani 1 1 d . . . H2 H -0.0320 0.1205 0.6878 0.048 Uiso 1 1 calc R . . O3 O -0.0377(3) 0.1553(4) 0.8290(2) 0.0299(7) Uani 1 1 d . . . O4 O 0.0263(2) 0.3411(3) 0.9477(2) 0.0297(7) Uani 1 1 d . . . O5 O 0.3484(3) 1.1953(4) 0.6656(3) 0.0366(8) Uani 1 1 d . . . O6 O 0.2965(2) 0.3947(4) 0.4727(2) 0.0395(8) Uani 1 1 d . . . H6E H 0.3095 0.3552 0.5355 0.059 Uiso 1 1 d R . . H6F H 0.3480 0.3805 0.4276 0.059 Uiso 1 1 d R . . C1 C 0.0770(3) 0.3525(5) 0.6598(3) 0.0193(8) Uani 1 1 d . . . C2 C 0.0712(3) 0.3726(5) 0.7690(3) 0.0183(8) Uani 1 1 d . . . C3 C 0.1545(3) 0.5825(5) 0.7029(3) 0.0183(8) Uani 1 1 d . . . C4 C 0.2028(3) 0.7433(5) 0.6936(3) 0.0196(8) Uani 1 1 d . . . C5 C 0.2531(4) 0.7956(6) 0.5987(3) 0.0283(10) Uani 1 1 d . . . H5 H 0.2554 0.7265 0.5400 0.034 Uiso 1 1 calc R . . C6 C 0.2984(4) 0.9454(6) 0.5911(3) 0.0303(10) Uani 1 1 d . . . H6 H 0.3297 0.9784 0.5273 0.036 Uiso 1 1 calc R . . C7 C 0.2977(4) 1.0483(5) 0.6791(3) 0.0265(9) Uani 1 1 d . . . C8 C 0.2479(4) 1.0013(5) 0.7728(4) 0.0267(9) Uani 1 1 d . . . H8 H 0.2464 1.0708 0.8314 0.032 Uiso 1 1 calc R . . C9 C 0.2005(3) 0.8517(5) 0.7789(3) 0.0264(9) Uani 1 1 d . . . H9 H 0.1659 0.8218 0.8418 0.032 Uiso 1 1 calc R . . C10 C 0.0360(3) 0.2262(5) 0.5851(3) 0.0245(9) Uani 1 1 d . . . C11 C 0.0156(3) 0.2809(5) 0.8531(3) 0.0227(9) Uani 1 1 d . . . C12 C 0.3815(4) 1.2831(6) 0.7607(4) 0.0422(13) Uani 1 1 d . . . H12C H 0.4154 1.3827 0.7408 0.063 Uiso 1 1 calc R . . H12A H 0.4364 1.2222 0.8044 0.063 Uiso 1 1 calc R . . H12B H 0.3152 1.3037 0.8011 0.063 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 Cu1 0.0283(2) 0.0229(2) 0.0112(2) -0.0002(3) 0.00305(15) 0.0026(3) N1 0.026(2) 0.018(2) 0.009(2) -0.0011(15) 0.0038(15) -0.0012(14) N2 0.021(2) 0.016(2) 0.015(2) 0.0018(15) -0.0026(17) -0.0012(14) O1 0.0473(18) 0.0348(17) 0.0144(15) -0.0048(13) 0.0036(12) -0.0092(14) O2 0.050(2) 0.0275(17) 0.0199(16) -0.0033(13) 0.0048(14) -0.0124(14) O3 0.0379(17) 0.0295(17) 0.0229(15) -0.0014(14) 0.0064(12) -0.0156(14) O4 0.0387(17) 0.0342(17) 0.0168(15) -0.0026(12) 0.0058(12) -0.0142(13) O5 0.051(2) 0.0232(17) 0.0355(19) 0.0049(14) 0.0021(16) -0.0113(15) O6 0.0290(16) 0.072(2) 0.0178(15) -0.0007(15) 0.0024(12) 0.0195(16) C1 0.0194(19) 0.020(2) 0.019(2) 0.0005(16) 0.0028(15) -0.0005(15) C2 0.020(2) 0.020(2) 0.0149(19) 0.0004(15) 0.0008(15) -0.0013(15) C3 0.016(2) 0.022(2) 0.017(2) 0.0006(17) -0.0004(16) 0.0038(15) C4 0.0191(19) 0.025(2) 0.0150(18) 0.0022(16) 0.0003(15) -0.0004(15) C5 0.037(3) 0.032(3) 0.017(2) -0.0012(19) 0.0023(19) -0.002(2) C6 0.037(3) 0.033(3) 0.021(2) 0.007(2) 0.0029(19) -0.005(2) C7 0.026(2) 0.026(2) 0.027(2) 0.0027(18) -0.0003(17) -0.0035(17) C8 0.034(2) 0.020(2) 0.026(2) -0.0020(16) 0.0008(19) 0.0004(17) C9 0.035(2) 0.023(2) 0.021(2) 0.0004(17) 0.0063(17) -0.0014(18) C10 0.031(2) 0.023(2) 0.020(2) -0.0047(17) 0.0032(17) -0.0020(17) C11 0.020(2) 0.030(2) 0.018(2) 0.0058(18) 0.0051(17) -0.0002(17) C12 0.042(3) 0.034(3) 0.050(3) -0.006(2) -0.002(2) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.971(5) . ? Cu1 O4 1.988(3) 2_564 ? Cu1 O6 1.998(3) . ? Cu1 N2 2.000(5) 2_564 ? Cu1 O1 2.270(3) . ? N1 C3 1.364(6) . ? N1 C1 1.368(6) . ? N2 C3 1.357(7) . ? N2 C2 1.374(5) . ? N2 Cu1 2.000(5) 2_565 ? O1 C10 1.213(5) . ? O2 C10 1.320(5) . ? O2 H2 0.8200 . ? O3 C11 1.248(5) . ? O4 C11 1.273(5) . ? O4 Cu1 1.988(3) 2_565 ? O5 C7 1.378(5) . ? O5 C12 1.421(5) . ? O6 H6E 0.8501 . ? O6 H6F 0.8500 . ? C1 C2 1.366(5) . ? C1 C10 1.465(5) . ? C2 C11 1.472(5) . ? C3 C4 1.465(5) . ? C4 C9 1.391(6) . ? C4 C5 1.411(5) . ? C5 C6 1.365(6) . ? C5 H5 0.9300 . ? C6 C7 1.387(6) . ? C6 H6 0.9300 . ? C7 C8 1.382(6) . ? C8 C9 1.371(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C12 H12C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 O4 89.15(15) . 2_564 ? N1 Cu1 O6 90.51(17) . . ? O4 Cu1 O6 149.73(13) 2_564 . ? N1 Cu1 N2 172.5(2) . 2_564 ? O4 Cu1 N2 83.96(14) 2_564 2_564 ? O6 Cu1 N2 96.99(16) . 2_564 ? N1 Cu1 O1 79.57(13) . . ? O4 Cu1 O1 112.62(12) 2_564 . ? O6 Cu1 O1 97.05(13) . . ? N2 Cu1 O1 100.22(13) 2_564 . ? C3 N1 C1 105.7(4) . . ? C3 N1 Cu1 140.5(3) . . ? C1 N1 Cu1 113.6(3) . . ? C3 N2 C2 106.4(4) . . ? C3 N2 Cu1 146.2(3) . 2_565 ? C2 N2 Cu1 106.5(3) . 2_565 ? C10 O1 Cu1 108.5(2) . . ? C10 O2 H2 109.5 . . ? C11 O4 Cu1 113.2(2) . 2_565 ? C7 O5 C12 117.3(3) . . ? Cu1 O6 H6E 109.4 . . ? Cu1 O6 H6F 133.3 . . ? H6E O6 H6F 116.6 . . ? C2 C1 N1 109.2(4) . . ? C2 C1 C10 132.8(4) . . ? N1 C1 C10 118.0(4) . . ? C1 C2 N2 108.0(4) . . ? C1 C2 C11 133.1(4) . . ? N2 C2 C11 118.7(4) . . ? N2 C3 N1 110.8(4) . . ? N2 C3 C4 124.6(4) . . ? N1 C3 C4 124.5(4) . . ? C9 C4 C5 117.0(4) . . ? C9 C4 C3 121.0(3) . . ? C5 C4 C3 122.0(4) . . ? C6 C5 C4 121.5(4) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? O5 C7 C8 124.0(4) . . ? O5 C7 C6 115.9(4) . . ? C8 C7 C6 120.1(4) . . ? C9 C8 C7 119.7(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C4 121.8(4) . . ? C8 C9 H9 119.1 . . ? C4 C9 H9 119.1 . . ? O1 C10 O2 121.7(4) . . ? O1 C10 C1 120.2(4) . . ? O2 C10 C1 118.0(3) . . ? O3 C11 O4 125.1(4) . . ? O3 C11 C2 120.2(4) . . ? O4 C11 C2 114.8(3) . . ? O5 C12 H12C 109.5 . . ? O5 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? 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 O4 Cu1 N1 C3 -62.3(6) 2_564 . . . ? O6 Cu1 N1 C3 87.4(6) . . . . ? O1 Cu1 N1 C3 -175.5(6) . . . . ? O4 Cu1 N1 C1 112.2(4) 2_564 . . . ? O6 Cu1 N1 C1 -98.0(3) . . . . ? O1 Cu1 N1 C1 -1.0(3) . . . . ? N1 Cu1 O1 C10 0.3(3) . . . . ? O4 Cu1 O1 C10 -84.3(3) 2_564 . . . ? O6 Cu1 O1 C10 89.6(3) . . . . ? N2 Cu1 O1 C10 -172.0(3) 2_564 . . . ? C3 N1 C1 C2 -0.2(5) . . . . ? Cu1 N1 C1 C2 -176.6(3) . . . . ? C3 N1 C1 C10 177.9(3) . . . . ? Cu1 N1 C1 C10 1.5(5) . . . . ? N1 C1 C2 N2 -0.6(4) . . . . ? C10 C1 C2 N2 -178.3(4) . . . . ? N1 C1 C2 C11 173.2(4) . . . . ? C10 C1 C2 C11 -4.5(7) . . . . ? C3 N2 C2 C1 1.2(5) . . . . ? Cu1 N2 C2 C1 -170.4(3) 2_565 . . . ? C3 N2 C2 C11 -173.7(3) . . . . ? Cu1 N2 C2 C11 14.7(4) 2_565 . . . ? C2 N2 C3 N1 -1.3(6) . . . . ? Cu1 N2 C3 N1 164.1(4) 2_565 . . . ? C2 N2 C3 C4 174.3(3) . . . . ? Cu1 N2 C3 C4 -20.2(8) 2_565 . . . ? C1 N1 C3 N2 1.0(6) . . . . ? Cu1 N1 C3 N2 175.7(3) . . . . ? C1 N1 C3 C4 -174.7(3) . . . . ? Cu1 N1 C3 C4 0.1(8) . . . . ? N2 C3 C4 C9 -10.9(6) . . . . ? N1 C3 C4 C9 164.2(4) . . . . ? N2 C3 C4 C5 169.4(4) . . . . ? N1 C3 C4 C5 -15.6(6) . . . . ? C9 C4 C5 C6 0.6(6) . . . . ? C3 C4 C5 C6 -179.6(4) . . . . ? C4 C5 C6 C7 1.4(7) . . . . ? C12 O5 C7 C8 19.3(6) . . . . ? C12 O5 C7 C6 -160.9(4) . . . . ? C5 C6 C7 O5 178.0(4) . . . . ? C5 C6 C7 C8 -2.2(7) . . . . ? O5 C7 C8 C9 -179.3(4) . . . . ? C6 C7 C8 C9 0.9(6) . . . . ? C7 C8 C9 C4 1.2(6) . . . . ? C5 C4 C9 C8 -1.9(6) . . . . ? C3 C4 C9 C8 178.3(4) . . . . ? Cu1 O1 C10 O2 179.0(3) . . . . ? Cu1 O1 C10 C1 0.4(4) . . . . ? C2 C1 C10 O1 176.3(4) . . . . ? N1 C1 C10 O1 -1.3(6) . . . . ? C2 C1 C10 O2 -2.4(6) . . . . ? N1 C1 C10 O2 180.0(4) . . . . ? Cu1 O4 C11 O3 171.8(3) 2_565 . . . ? Cu1 O4 C11 C2 -8.9(4) 2_565 . . . ? C1 C2 C11 O3 1.6(6) . . . . ? N2 C2 C11 O3 174.9(4) . . . . ? C1 C2 C11 O4 -177.8(4) . . . . ? N2 C2 C11 O4 -4.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 1.77 2.581(4) 167.4 . O6 H6E O5 0.85 2.12 2.945(4) 163.2 1_545 O6 H6F O3 0.85 1.88 2.731(4) 178.8 4_554 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.555 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.070 # Attachment '- 2.cif' data_cxj33_0m #TrackingRef '- 2.cif' _database_code_depnum_ccdc_archive 'CCDC 854848' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N4 O5 Zn' _chemical_formula_weight 481.78 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.550(4) _cell_length_b 12.839(3) _cell_length_c 18.150(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4089.6(16) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 1.245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7713 _exptl_absorpt_correction_T_max 0.7889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35437 _diffrn_reflns_av_R_equivalents 0.1064 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4711 _reflns_number_gt 2564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0737P)^2^+0.5860P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4711 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1536 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 Zn1 Zn 0.24268(2) 0.70009(3) 0.49902(3) 0.03785(17) Uani 1 1 d . . . O1 O 0.14624(14) 0.6646(2) 0.42891(15) 0.0473(7) Uani 1 1 d . . . O2 O 0.09802(18) 0.5381(2) 0.36061(18) 0.0579(8) Uani 1 1 d . . . H2A H 0.1061 0.4761 0.3530 0.087 Uiso 1 1 calc R . . O3 O 0.11544(17) 0.3480(2) 0.34795(16) 0.0571(8) Uani 1 1 d . . . O4 O 0.18325(17) 0.2228(2) 0.40193(15) 0.0492(7) Uani 1 1 d . . . O5 O 0.54329(16) 0.5123(2) 0.69851(15) 0.0578(8) Uani 1 1 d . . . N1 N 0.26893(17) 0.3644(2) 0.47871(17) 0.0358(7) Uani 1 1 d . . . N2 N 0.25259(16) 0.5370(2) 0.49007(16) 0.0355(8) Uani 1 1 d . . . N3 N 0.33337(17) 0.7405(2) 0.57329(18) 0.0413(8) Uani 1 1 d . . . N4 N 0.18762(18) 0.7066(2) 0.60344(18) 0.0409(8) Uani 1 1 d . . . C1 C 0.1458(2) 0.5723(3) 0.4083(2) 0.0401(9) Uani 1 1 d . . . C2 C 0.2008(2) 0.4995(3) 0.4408(2) 0.0373(9) Uani 1 1 d . . . C3 C 0.2107(2) 0.3947(3) 0.4331(2) 0.0368(9) Uani 1 1 d . . . C4 C 0.1676(2) 0.3168(3) 0.3914(2) 0.0430(10) Uani 1 1 d . . . C5 C 0.2926(2) 0.4518(3) 0.51094(19) 0.0343(9) Uani 1 1 d . . . C6 C 0.3569(2) 0.4580(3) 0.5624(2) 0.0358(9) Uani 1 1 d . . . C7 C 0.3507(2) 0.5111(3) 0.6287(2) 0.0422(10) Uani 1 1 d . . . H7 H 0.3035 0.5370 0.6431 0.051 Uiso 1 1 calc R . . C8 C 0.4131(2) 0.5264(3) 0.6737(2) 0.0466(10) Uani 1 1 d . . . H8 H 0.4077 0.5616 0.7182 0.056 Uiso 1 1 calc R . . C9 C 0.4840(2) 0.4890(3) 0.6523(2) 0.0420(10) Uani 1 1 d . . . C10 C 0.4909(2) 0.4333(3) 0.5886(2) 0.0513(11) Uani 1 1 d . . . H10 H 0.5379 0.4062 0.5747 0.062 Uiso 1 1 calc R . . C11 C 0.4272(2) 0.4173(3) 0.5444(2) 0.0490(10) Uani 1 1 d . . . H11 H 0.4321 0.3780 0.5016 0.059 Uiso 1 1 calc R . . C12 C 0.6184(2) 0.5042(4) 0.6692(3) 0.0627(13) Uani 1 1 d . . . H12A H 0.6546 0.5265 0.7056 0.094 Uiso 1 1 calc R . . H12B H 0.6227 0.5475 0.6263 0.094 Uiso 1 1 calc R . . H12C H 0.6285 0.4331 0.6560 0.094 Uiso 1 1 calc R . . C13 C 0.4058(2) 0.7550(3) 0.5554(3) 0.0522(11) Uani 1 1 d . . . H13 H 0.4218 0.7360 0.5085 0.063 Uiso 1 1 calc R . . C14 C 0.4584(3) 0.7966(4) 0.6030(3) 0.0676(14) Uani 1 1 d . . . H14 H 0.5087 0.8063 0.5885 0.081 Uiso 1 1 calc R . . C15 C 0.4350(3) 0.8236(4) 0.6722(3) 0.0743(16) Uani 1 1 d . . . H15 H 0.4693 0.8525 0.7055 0.089 Uiso 1 1 calc R . . C16 C 0.3606(3) 0.8077(4) 0.6922(3) 0.0643(13) Uani 1 1 d . . . H16 H 0.3441 0.8244 0.7395 0.077 Uiso 1 1 calc R . . C17 C 0.3104(2) 0.7667(3) 0.6414(2) 0.0436(10) Uani 1 1 d . . . C18 C 0.2292(2) 0.7453(3) 0.6591(2) 0.0416(9) Uani 1 1 d . . . C19 C 0.1988(3) 0.7625(3) 0.7278(2) 0.0606(12) Uani 1 1 d . . . H19 H 0.2289 0.7890 0.7655 0.073 Uiso 1 1 calc R . . C20 C 0.1235(3) 0.7402(4) 0.7401(3) 0.0691(14) Uani 1 1 d . . . H20 H 0.1021 0.7515 0.7863 0.083 Uiso 1 1 calc R . . C21 C 0.0798(3) 0.7008(4) 0.6834(3) 0.0688(15) Uani 1 1 d . . . H21 H 0.0285 0.6851 0.6905 0.083 Uiso 1 1 calc R . . C22 C 0.1141(2) 0.6853(3) 0.6160(3) 0.0559(12) Uani 1 1 d . . . H22 H 0.0849 0.6588 0.5776 0.067 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 Zn1 0.0423(3) 0.0261(2) 0.0452(3) -0.0020(2) -0.0019(2) -0.00160(17) O1 0.0455(16) 0.0318(15) 0.065(2) -0.0042(14) -0.0161(14) 0.0036(12) O2 0.061(2) 0.0419(18) 0.070(2) -0.0094(16) -0.0286(17) 0.0059(15) O3 0.062(2) 0.0459(18) 0.0633(19) -0.0065(15) -0.0294(17) 0.0006(15) O4 0.0643(19) 0.0306(16) 0.0528(18) -0.0039(13) -0.0152(14) -0.0043(13) O5 0.0506(19) 0.069(2) 0.0542(19) -0.0120(16) -0.0131(15) -0.0014(15) N1 0.0418(18) 0.0271(17) 0.0384(17) 0.0010(14) -0.0059(14) -0.0025(13) N2 0.0388(19) 0.0244(17) 0.043(2) -0.0018(14) -0.0060(14) 0.0010(12) N3 0.0395(19) 0.0367(19) 0.048(2) -0.0032(16) -0.0014(15) -0.0018(15) N4 0.0375(18) 0.0345(18) 0.050(2) 0.0012(15) 0.0004(16) -0.0012(14) C1 0.042(2) 0.031(2) 0.047(2) -0.0001(18) -0.0065(19) 0.0010(17) C2 0.038(2) 0.028(2) 0.046(2) 0.0042(18) -0.0069(18) -0.0017(16) C3 0.039(2) 0.030(2) 0.041(2) -0.0007(17) -0.0010(18) -0.0011(16) C4 0.051(3) 0.034(2) 0.044(2) -0.0048(19) -0.004(2) -0.0033(18) C5 0.041(2) 0.0245(19) 0.037(2) 0.0017(16) -0.0026(17) 0.0004(15) C6 0.037(2) 0.031(2) 0.039(2) -0.0019(17) -0.0042(17) -0.0016(16) C7 0.038(2) 0.042(2) 0.047(2) 0.003(2) 0.0009(18) 0.0059(18) C8 0.052(3) 0.049(3) 0.039(2) -0.0061(19) -0.004(2) 0.000(2) C9 0.046(3) 0.043(2) 0.037(2) -0.0007(19) -0.0090(17) -0.0026(19) C10 0.035(2) 0.057(3) 0.062(3) -0.014(2) -0.008(2) 0.0067(19) C11 0.051(3) 0.045(2) 0.051(3) -0.014(2) -0.008(2) 0.004(2) C12 0.042(3) 0.072(3) 0.074(3) -0.008(3) -0.014(2) 0.005(2) C13 0.043(3) 0.051(3) 0.062(3) -0.007(2) -0.004(2) -0.001(2) C14 0.046(3) 0.074(4) 0.083(4) -0.015(3) -0.004(3) -0.008(2) C15 0.054(3) 0.090(4) 0.079(4) -0.027(3) -0.020(3) -0.013(3) C16 0.053(3) 0.075(3) 0.065(3) -0.020(3) -0.006(2) -0.006(2) C17 0.044(2) 0.037(2) 0.049(2) -0.004(2) -0.002(2) 0.0015(18) C18 0.049(2) 0.033(2) 0.043(2) 0.0022(19) 0.0022(19) 0.0015(18) C19 0.063(3) 0.068(3) 0.050(3) -0.007(2) 0.006(2) 0.002(2) C20 0.071(4) 0.077(4) 0.059(3) 0.007(3) 0.023(3) 0.006(3) C21 0.050(3) 0.076(4) 0.080(4) 0.017(3) 0.020(3) 0.001(2) C22 0.044(3) 0.057(3) 0.067(3) 0.012(2) 0.000(2) -0.002(2) _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 Zn1 N2 2.108(3) . ? Zn1 N4 2.129(3) . ? Zn1 N3 2.149(3) . ? Zn1 N1 2.151(3) 7_665 ? Zn1 O1 2.166(3) . ? Zn1 O4 2.209(3) 7_665 ? O1 C1 1.243(4) . ? O2 C1 1.283(4) . ? O2 H2A 0.8200 . ? O3 C4 1.274(5) . ? O4 C4 1.252(4) . ? O4 Zn1 2.209(3) 7_655 ? O5 C9 1.369(4) . ? O5 C12 1.426(5) . ? N1 C5 1.332(4) . ? N1 C3 1.371(4) . ? N1 Zn1 2.151(3) 7_655 ? N2 C5 1.354(4) . ? N2 C2 1.363(4) . ? N3 C13 1.325(5) . ? N3 C17 1.342(5) . ? N4 C22 1.339(5) . ? N4 C18 1.342(5) . ? C1 C2 1.467(5) . ? C2 C3 1.364(5) . ? C3 C4 1.465(5) . ? C5 C6 1.466(5) . ? C6 C11 1.379(5) . ? C6 C7 1.387(5) . ? C7 C8 1.381(5) . ? C7 H7 0.9300 . ? C8 C9 1.388(5) . ? C8 H8 0.9300 . ? C9 C10 1.366(5) . ? C10 C11 1.390(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.373(6) . ? C13 H13 0.9300 . ? C14 C15 1.366(7) . ? C14 H14 0.9300 . ? C15 C16 1.371(6) . ? C15 H15 0.9300 . ? C16 C17 1.380(6) . ? C16 H16 0.9300 . ? C17 C18 1.487(5) . ? C18 C19 1.375(6) . ? C19 C20 1.369(6) . ? C19 H19 0.9300 . ? C20 C21 1.380(7) . ? C20 H20 0.9300 . ? C21 C22 1.377(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 N2 Zn1 N4 98.35(11) . . ? N2 Zn1 N3 103.14(12) . . ? N4 Zn1 N3 76.61(12) . . ? N2 Zn1 N1 165.69(12) . 7_665 ? N4 Zn1 N1 94.07(11) . 7_665 ? N3 Zn1 N1 86.60(12) . 7_665 ? N2 Zn1 O1 79.07(10) . . ? N4 Zn1 O1 100.17(11) . . ? N3 Zn1 O1 176.27(11) . . ? N1 Zn1 O1 91.79(11) 7_665 . ? N2 Zn1 O4 91.22(11) . 7_665 ? N4 Zn1 O4 166.40(11) . 7_665 ? N3 Zn1 O4 91.87(12) . 7_665 ? N1 Zn1 O4 77.84(10) 7_665 7_665 ? O1 Zn1 O4 91.08(11) . 7_665 ? C1 O1 Zn1 112.5(2) . . ? C1 O2 H2A 109.5 . . ? C4 O4 Zn1 112.2(2) . 7_655 ? C9 O5 C12 117.3(3) . . ? C5 N1 C3 105.0(3) . . ? C5 N1 Zn1 141.3(2) . 7_655 ? C3 N1 Zn1 108.2(2) . 7_655 ? C5 N2 C2 104.2(3) . . ? C5 N2 Zn1 145.5(2) . . ? C2 N2 Zn1 110.2(2) . . ? C13 N3 C17 118.6(4) . . ? C13 N3 Zn1 126.2(3) . . ? C17 N3 Zn1 114.6(3) . . ? C22 N4 C18 118.1(4) . . ? C22 N4 Zn1 125.6(3) . . ? C18 N4 Zn1 116.0(3) . . ? O1 C1 O2 122.3(3) . . ? O1 C1 C2 118.8(3) . . ? O2 C1 C2 118.9(3) . . ? N2 C2 C3 109.2(3) . . ? N2 C2 C1 118.6(3) . . ? C3 C2 C1 132.2(3) . . ? C2 C3 N1 108.3(3) . . ? C2 C3 C4 131.4(4) . . ? N1 C3 C4 120.1(3) . . ? O4 C4 O3 123.7(4) . . ? O4 C4 C3 117.8(4) . . ? O3 C4 C3 118.5(4) . . ? N1 C5 N2 113.3(3) . . ? N1 C5 C6 124.5(3) . . ? N2 C5 C6 122.2(3) . . ? C11 C6 C7 117.5(4) . . ? C11 C6 C5 121.1(4) . . ? C7 C6 C5 121.2(3) . . ? C8 C7 C6 121.4(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 119.8(4) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 O5 124.5(4) . . ? C10 C9 C8 119.8(4) . . ? O5 C9 C8 115.7(3) . . ? C9 C10 C11 119.6(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C6 C11 C10 121.8(4) . . ? C6 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 123.1(4) . . ? N3 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C15 C14 C13 118.4(4) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C16 119.5(4) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C17 119.1(5) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? N3 C17 C16 121.3(4) . . ? N3 C17 C18 116.1(3) . . ? C16 C17 C18 122.5(4) . . ? N4 C18 C19 122.0(4) . . ? N4 C18 C17 115.3(3) . . ? C19 C18 C17 122.7(4) . . ? C20 C19 C18 119.3(5) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 119.5(4) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 118.1(5) . . ? C22 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? N4 C22 C21 122.9(5) . . ? N4 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Zn1 O1 C1 -8.3(3) . . . . ? N4 Zn1 O1 C1 -105.0(3) . . . . ? N3 Zn1 O1 C1 -135.0(16) . . . . ? N1 Zn1 O1 C1 160.6(3) 7_665 . . . ? O4 Zn1 O1 C1 82.7(3) 7_665 . . . ? N4 Zn1 N2 C5 -79.6(4) . . . . ? N3 Zn1 N2 C5 -1.5(5) . . . . ? N1 Zn1 N2 C5 130.5(5) 7_665 . . . ? O1 Zn1 N2 C5 -178.4(5) . . . . ? O4 Zn1 N2 C5 90.7(4) 7_665 . . . ? N4 Zn1 N2 C2 105.3(3) . . . . ? N3 Zn1 N2 C2 -176.6(2) . . . . ? N1 Zn1 N2 C2 -44.6(6) 7_665 . . . ? O1 Zn1 N2 C2 6.5(2) . . . . ? O4 Zn1 N2 C2 -84.4(2) 7_665 . . . ? N2 Zn1 N3 C13 83.2(3) . . . . ? N4 Zn1 N3 C13 178.8(3) . . . . ? N1 Zn1 N3 C13 -86.2(3) 7_665 . . . ? O1 Zn1 N3 C13 -150.8(16) . . . . ? O4 Zn1 N3 C13 -8.5(3) 7_665 . . . ? N2 Zn1 N3 C17 -106.4(3) . . . . ? N4 Zn1 N3 C17 -10.8(3) . . . . ? N1 Zn1 N3 C17 84.2(3) 7_665 . . . ? O1 Zn1 N3 C17 19.6(18) . . . . ? O4 Zn1 N3 C17 161.9(3) 7_665 . . . ? N2 Zn1 N4 C22 -76.0(3) . . . . ? N3 Zn1 N4 C22 -177.6(3) . . . . ? N1 Zn1 N4 C22 96.9(3) 7_665 . . . ? O1 Zn1 N4 C22 4.3(3) . . . . ? O4 Zn1 N4 C22 149.7(4) 7_665 . . . ? N2 Zn1 N4 C18 110.9(3) . . . . ? N3 Zn1 N4 C18 9.3(3) . . . . ? N1 Zn1 N4 C18 -76.2(3) 7_665 . . . ? O1 Zn1 N4 C18 -168.8(3) . . . . ? O4 Zn1 N4 C18 -23.4(6) 7_665 . . . ? Zn1 O1 C1 O2 -172.8(3) . . . . ? Zn1 O1 C1 C2 8.5(4) . . . . ? C5 N2 C2 C3 -0.2(4) . . . . ? Zn1 N2 C2 C3 176.9(2) . . . . ? C5 N2 C2 C1 178.3(3) . . . . ? Zn1 N2 C2 C1 -4.5(4) . . . . ? O1 C1 C2 N2 -2.9(6) . . . . ? O2 C1 C2 N2 178.4(4) . . . . ? O1 C1 C2 C3 175.2(4) . . . . ? O2 C1 C2 C3 -3.5(7) . . . . ? N2 C2 C3 N1 0.9(4) . . . . ? C1 C2 C3 N1 -177.4(4) . . . . ? N2 C2 C3 C4 175.4(4) . . . . ? C1 C2 C3 C4 -2.8(7) . . . . ? C5 N1 C3 C2 -1.2(4) . . . . ? Zn1 N1 C3 C2 158.5(2) 7_655 . . . ? C5 N1 C3 C4 -176.4(3) . . . . ? Zn1 N1 C3 C4 -16.7(4) 7_655 . . . ? Zn1 O4 C4 O3 -166.6(3) 7_655 . . . ? Zn1 O4 C4 C3 11.7(5) 7_655 . . . ? C2 C3 C4 O4 -170.5(4) . . . . ? N1 C3 C4 O4 3.6(6) . . . . ? C2 C3 C4 O3 8.0(7) . . . . ? N1 C3 C4 O3 -178.0(4) . . . . ? C3 N1 C5 N2 1.1(4) . . . . ? Zn1 N1 C5 N2 -147.1(3) 7_655 . . . ? C3 N1 C5 C6 -177.2(3) . . . . ? Zn1 N1 C5 C6 34.6(6) 7_655 . . . ? C2 N2 C5 N1 -0.6(4) . . . . ? Zn1 N2 C5 N1 -175.8(3) . . . . ? C2 N2 C5 C6 177.8(3) . . . . ? Zn1 N2 C5 C6 2.5(7) . . . . ? N1 C5 C6 C11 51.8(6) . . . . ? N2 C5 C6 C11 -126.3(4) . . . . ? N1 C5 C6 C7 -132.6(4) . . . . ? N2 C5 C6 C7 49.3(5) . . . . ? C11 C6 C7 C8 2.5(6) . . . . ? C5 C6 C7 C8 -173.2(3) . . . . ? C6 C7 C8 C9 0.7(6) . . . . ? C12 O5 C9 C10 18.2(6) . . . . ? C12 O5 C9 C8 -161.5(4) . . . . ? C7 C8 C9 C10 -3.0(6) . . . . ? C7 C8 C9 O5 176.7(4) . . . . ? O5 C9 C10 C11 -177.7(4) . . . . ? C8 C9 C10 C11 2.0(6) . . . . ? C7 C6 C11 C10 -3.6(6) . . . . ? C5 C6 C11 C10 172.2(4) . . . . ? C9 C10 C11 C6 1.3(7) . . . . ? C17 N3 C13 C14 -0.8(6) . . . . ? Zn1 N3 C13 C14 169.3(3) . . . . ? N3 C13 C14 C15 0.6(7) . . . . ? C13 C14 C15 C16 0.5(8) . . . . ? C14 C15 C16 C17 -1.3(8) . . . . ? C13 N3 C17 C16 0.0(6) . . . . ? Zn1 N3 C17 C16 -171.3(3) . . . . ? C13 N3 C17 C18 -177.9(3) . . . . ? Zn1 N3 C17 C18 10.8(4) . . . . ? C15 C16 C17 N3 1.1(7) . . . . ? C15 C16 C17 C18 178.9(4) . . . . ? C22 N4 C18 C19 0.5(6) . . . . ? Zn1 N4 C18 C19 174.1(3) . . . . ? C22 N4 C18 C17 179.7(3) . . . . ? Zn1 N4 C18 C17 -6.6(4) . . . . ? N3 C17 C18 N4 -2.9(5) . . . . ? C16 C17 C18 N4 179.2(4) . . . . ? N3 C17 C18 C19 176.3(4) . . . . ? C16 C17 C18 C19 -1.6(6) . . . . ? N4 C18 C19 C20 -0.3(7) . . . . ? C17 C18 C19 C20 -179.5(4) . . . . ? C18 C19 C20 C21 0.1(7) . . . . ? C19 C20 C21 C22 0.1(7) . . . . ? C18 N4 C22 C21 -0.3(6) . . . . ? Zn1 N4 C22 C21 -173.3(3) . . . . ? C20 C21 C22 N4 0.1(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O3 0.82 1.66 2.471(4) 172.2 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.653 _refine_diff_density_min -0.745 _refine_diff_density_rms 0.083 # Attachment '- 3.cif' data_p1 #TrackingRef '- 3.cif' _database_code_depnum_ccdc_archive 'CCDC 854849' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Co N4 O5' _chemical_formula_weight 475.32 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.4706(18) _cell_length_b 12.8946(13) _cell_length_c 18.194(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4098.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 0.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8366 _exptl_absorpt_correction_T_max 0.8719 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19534 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3518 _reflns_number_gt 2795 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0660P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3518 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.243108(17) 0.79652(2) 1.004148(14) 0.02966(14) Uani 1 1 d . . . N2 N 0.25349(9) 0.96035(14) 1.01085(9) 0.0293(5) Uani 1 1 d . . . N1 N 0.26944(11) 1.13298(13) 1.02147(10) 0.0304(4) Uani 1 1 d . . . N3 N 0.33176(11) 0.75598(14) 0.92962(9) 0.0345(4) Uani 1 1 d . . . N4 N 0.18653(12) 0.79505(14) 0.90106(10) 0.0360(5) Uani 1 1 d . . . O1 O 0.14902(9) 0.83276(12) 1.07564(8) 0.0418(4) Uani 1 1 d . . . O2 O 0.10104(11) 0.95938(13) 1.14329(9) 0.0519(5) Uani 1 1 d . . . H2A H 0.1083 1.0215 1.1500 0.078 Uiso 1 1 calc R . . O3 O 0.11900(11) 1.14984(12) 1.15570(8) 0.0508(5) Uani 1 1 d . . . O4 O 0.18586(10) 1.27461(12) 1.09965(8) 0.0413(4) Uani 1 1 d . . . O5 O 0.54471(10) 0.98773(14) 0.80099(8) 0.0518(5) Uani 1 1 d . . . C1 C 0.14831(13) 0.92556(18) 1.09497(11) 0.0350(5) Uani 1 1 d . . . C2 C 0.20229(12) 0.99754(15) 1.06110(10) 0.0310(5) Uani 1 1 d . . . C3 C 0.21222(13) 1.10221(15) 1.06801(10) 0.0301(5) Uani 1 1 d . . . C4 C 0.16987(15) 1.18057(17) 1.11064(11) 0.0360(6) Uani 1 1 d . . . C5 C 0.29278(14) 1.04544(15) 0.98846(10) 0.0292(5) Uani 1 1 d . . . C6 C 0.35773(13) 1.03941(15) 0.93717(11) 0.0310(5) Uani 1 1 d . . . C11 C 0.42764(13) 1.08228(18) 0.95472(12) 0.0405(6) Uani 1 1 d . . . H11 H 0.4321 1.1222 0.9971 0.049 Uiso 1 1 calc R . . C10 C 0.49154(15) 1.0673(2) 0.91066(12) 0.0455(6) Uani 1 1 d . . . H10 H 0.5384 1.0960 0.9238 0.055 Uiso 1 1 calc R . . C9 C 0.48476(14) 1.00917(17) 0.84689(11) 0.0372(6) Uani 1 1 d . . . C8 C 0.41408(14) 0.97030(18) 0.82703(12) 0.0406(6) Uani 1 1 d . . . H8 H 0.4089 0.9337 0.7833 0.049 Uiso 1 1 calc R . . C7 C 0.35181(14) 0.98503(18) 0.87101(11) 0.0381(6) Uani 1 1 d . . . H7 H 0.3046 0.9584 0.8567 0.046 Uiso 1 1 calc R . . C12 C 0.61983(15) 0.9966(2) 0.82953(15) 0.0570(7) Uani 1 1 d . . . H12A H 0.6562 0.9799 0.7918 0.086 Uiso 1 1 calc R . . H12B H 0.6259 0.9496 0.8700 0.086 Uiso 1 1 calc R . . H12C H 0.6283 1.0664 0.8461 0.086 Uiso 1 1 calc R . . C13 C 0.40506(14) 0.7412(2) 0.94689(13) 0.0471(6) Uani 1 1 d . . . H13 H 0.4214 0.7589 0.9939 0.056 Uiso 1 1 calc R . . C14 C 0.45770(17) 0.7009(2) 0.89853(16) 0.0640(8) Uani 1 1 d . . . H14 H 0.5084 0.6910 0.9125 0.077 Uiso 1 1 calc R . . C15 C 0.43333(18) 0.6756(3) 0.82918(17) 0.0709(9) Uani 1 1 d . . . H15 H 0.4674 0.6473 0.7954 0.085 Uiso 1 1 calc R . . C16 C 0.35897(17) 0.6922(2) 0.80999(14) 0.0564(8) Uani 1 1 d . . . H16 H 0.3423 0.6766 0.7627 0.068 Uiso 1 1 calc R . . C17 C 0.30829(15) 0.73238(17) 0.86113(11) 0.0374(6) Uani 1 1 d . . . C18 C 0.22761(15) 0.75495(17) 0.84521(11) 0.0374(6) Uani 1 1 d . . . C19 C 0.19493(17) 0.7393(2) 0.77681(13) 0.0544(7) Uani 1 1 d . . . H19 H 0.2239 0.7119 0.7386 0.065 Uiso 1 1 calc R . . C20 C 0.11929(19) 0.7644(3) 0.76577(16) 0.0673(9) Uani 1 1 d . . . H20 H 0.0966 0.7538 0.7201 0.081 Uiso 1 1 calc R . . C21 C 0.07788(17) 0.8050(2) 0.82246(16) 0.0648(9) Uani 1 1 d . . . H21 H 0.0267 0.8226 0.8161 0.078 Uiso 1 1 calc R . . C22 C 0.11341(16) 0.8195(2) 0.88954(14) 0.0513(7) Uani 1 1 d . . . H22 H 0.0852 0.8474 0.9281 0.062 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 Co1 0.0382(3) 0.0145(2) 0.0364(2) -0.00142(10) 0.00115(12) 0.00056(12) N2 0.0373(13) 0.0138(11) 0.0368(10) -0.0009(7) 0.0056(7) 0.0002(7) N1 0.0408(12) 0.0155(10) 0.0349(8) 0.0006(7) 0.0056(8) 0.0013(8) N3 0.0379(13) 0.0221(10) 0.0435(10) -0.0020(7) 0.0010(8) 0.0030(9) N4 0.0380(13) 0.0258(11) 0.0441(10) 0.0045(7) -0.0047(8) 0.0005(9) O1 0.0478(11) 0.0201(9) 0.0575(10) -0.0018(7) 0.0151(7) -0.0063(8) O2 0.0647(13) 0.0317(10) 0.0592(10) -0.0065(7) 0.0302(9) -0.0071(9) O3 0.0676(13) 0.0309(10) 0.0539(9) -0.0056(7) 0.0294(9) 0.0010(9) O4 0.0585(12) 0.0194(9) 0.0459(8) -0.0054(6) 0.0124(7) 0.0023(8) O5 0.0488(12) 0.0610(13) 0.0456(9) -0.0111(8) 0.0126(8) 0.0028(10) C1 0.0405(15) 0.0245(13) 0.0398(11) -0.0007(9) 0.0073(10) -0.0016(11) C2 0.0392(14) 0.0185(11) 0.0353(10) 0.0014(8) 0.0052(9) 0.0008(10) C3 0.0376(14) 0.0204(11) 0.0323(10) -0.0016(8) 0.0037(9) 0.0013(10) C4 0.0507(16) 0.0217(12) 0.0357(11) -0.0045(9) 0.0049(10) 0.0028(11) C5 0.0372(15) 0.0158(12) 0.0345(10) -0.0005(7) 0.0015(9) -0.0001(10) C6 0.0377(14) 0.0183(12) 0.0370(11) 0.0007(8) 0.0050(9) 0.0018(10) C11 0.0493(16) 0.0324(13) 0.0397(11) -0.0109(9) 0.0071(10) -0.0044(12) C10 0.0415(16) 0.0429(15) 0.0521(13) -0.0090(11) 0.0075(11) -0.0088(13) C9 0.0429(16) 0.0328(13) 0.0358(11) 0.0000(9) 0.0090(9) 0.0043(12) C8 0.0539(18) 0.0352(14) 0.0328(11) -0.0075(9) 0.0027(10) 0.0014(12) C7 0.0439(16) 0.0316(13) 0.0389(11) -0.0019(9) 0.0012(10) -0.0042(11) C12 0.0410(18) 0.064(2) 0.0660(16) -0.0053(14) 0.0147(13) -0.0056(15) C13 0.0395(17) 0.0460(16) 0.0557(14) -0.0042(11) -0.0016(11) 0.0040(13) C14 0.0406(19) 0.073(2) 0.0787(19) -0.0088(15) 0.0051(14) 0.0124(16) C15 0.060(2) 0.078(2) 0.0741(19) -0.0255(16) 0.0230(16) 0.0089(18) C16 0.057(2) 0.060(2) 0.0524(15) -0.0171(13) 0.0065(13) 0.0010(15) C17 0.0458(16) 0.0262(13) 0.0403(12) -0.0033(9) 0.0033(10) -0.0010(11) C18 0.0513(17) 0.0237(12) 0.0371(11) 0.0019(9) -0.0012(10) -0.0032(12) C19 0.064(2) 0.0510(18) 0.0487(13) -0.0017(11) -0.0121(13) -0.0040(15) C20 0.073(2) 0.072(2) 0.0568(16) 0.0096(14) -0.0226(16) -0.0110(18) C21 0.0460(19) 0.069(2) 0.080(2) 0.0222(15) -0.0224(15) -0.0016(15) C22 0.0444(18) 0.0490(17) 0.0605(15) 0.0111(12) -0.0038(12) 0.0094(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N4 2.1202(18) . ? Co1 N3 2.1238(18) . ? Co1 N2 2.1238(18) . ? Co1 N1 2.1434(18) 8_655 ? Co1 O1 2.1476(15) . ? Co1 O4 2.1538(15) 8_655 ? N2 C5 1.357(3) . ? N2 C2 1.366(2) . ? N1 C5 1.342(3) . ? N1 C3 1.369(3) . ? N1 Co1 2.1434(18) 8_665 ? N3 C13 1.332(3) . ? N3 C17 1.347(3) . ? N4 C22 1.332(3) . ? N4 C18 1.347(3) . ? O1 C1 1.247(3) . ? O2 C1 1.282(3) . ? O2 H2A 0.8200 . ? O3 C4 1.272(3) . ? O4 C4 1.260(3) . ? O4 Co1 2.1538(15) 8_665 ? O5 C9 1.368(3) . ? O5 C12 1.416(3) . ? C1 C2 1.460(3) . ? C2 C3 1.367(3) . ? C3 C4 1.473(3) . ? C5 C6 1.471(3) . ? C6 C11 1.378(3) . ? C6 C7 1.397(3) . ? C11 C10 1.388(3) . ? C11 H11 0.9300 . ? C10 C9 1.387(3) . ? C10 H10 0.9300 . ? C9 C8 1.381(3) . ? C8 C7 1.364(3) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.375(3) . ? C13 H13 0.9300 . ? C14 C15 1.371(4) . ? C14 H14 0.9300 . ? C15 C16 1.362(4) . ? C15 H15 0.9300 . ? C16 C17 1.385(3) . ? C16 H16 0.9300 . ? C17 C18 1.468(3) . ? C18 C19 1.384(3) . ? C19 C20 1.375(4) . ? C19 H19 0.9300 . ? C20 C21 1.364(4) . ? C20 H20 0.9300 . ? C21 C22 1.382(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 N4 Co1 N3 76.88(7) . . ? N4 Co1 N2 95.71(7) . . ? N3 Co1 N2 102.66(7) . . ? N4 Co1 N1 94.22(7) . 8_655 ? N3 Co1 N1 85.78(7) . 8_655 ? N2 Co1 N1 168.21(7) . 8_655 ? N4 Co1 O1 100.42(7) . . ? N3 Co1 O1 176.76(6) . . ? N2 Co1 O1 79.29(6) . . ? N1 Co1 O1 92.68(7) 8_655 . ? N4 Co1 O4 168.85(7) . 8_655 ? N3 Co1 O4 93.59(7) . 8_655 ? N2 Co1 O4 92.00(6) . 8_655 ? N1 Co1 O4 79.12(6) 8_655 8_655 ? O1 Co1 O4 88.91(6) . 8_655 ? C5 N2 C2 104.38(17) . . ? C5 N2 Co1 146.14(14) . . ? C2 N2 Co1 109.37(13) . . ? C5 N1 C3 104.77(17) . . ? C5 N1 Co1 142.44(14) . 8_665 ? C3 N1 Co1 107.54(13) . 8_665 ? C13 N3 C17 118.6(2) . . ? C13 N3 Co1 125.85(15) . . ? C17 N3 Co1 115.11(15) . . ? C22 N4 C18 118.9(2) . . ? C22 N4 Co1 125.74(16) . . ? C18 N4 Co1 114.98(16) . . ? C1 O1 Co1 112.78(14) . . ? C1 O2 H2A 109.5 . . ? C4 O4 Co1 112.45(13) . 8_665 ? C9 O5 C12 118.00(19) . . ? O1 C1 O2 121.7(2) . . ? O1 C1 C2 118.99(19) . . ? O2 C1 C2 119.3(2) . . ? N2 C2 C3 108.97(18) . . ? N2 C2 C1 118.84(18) . . ? C3 C2 C1 132.17(19) . . ? C2 C3 N1 108.79(17) . . ? C2 C3 C4 131.5(2) . . ? N1 C3 C4 119.59(18) . . ? O4 C4 O3 123.8(2) . . ? O4 C4 C3 117.7(2) . . ? O3 C4 C3 118.5(2) . . ? N1 C5 N2 113.09(18) . . ? N1 C5 C6 124.24(18) . . ? N2 C5 C6 122.54(18) . . ? C11 C6 C7 117.81(19) . . ? C11 C6 C5 121.03(18) . . ? C7 C6 C5 121.1(2) . . ? C6 C11 C10 121.6(2) . . ? C6 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C9 C10 C11 119.3(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? O5 C9 C8 116.85(19) . . ? O5 C9 C10 123.7(2) . . ? C8 C9 C10 119.5(2) . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C7 C6 121.1(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 123.1(2) . . ? N3 C13 H13 118.4 . . ? C14 C13 H13 118.4 . . ? C15 C14 C13 118.1(3) . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 121.0 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.8(3) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? N3 C17 C16 120.8(2) . . ? N3 C17 C18 115.48(18) . . ? C16 C17 C18 123.7(2) . . ? N4 C18 C19 121.0(2) . . ? N4 C18 C17 116.01(19) . . ? C19 C18 C17 123.0(2) . . ? C20 C19 C18 119.6(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 119.3(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 118.8(3) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? N4 C22 C21 122.5(3) . . ? N4 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? 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 N4 Co1 N2 C5 -79.1(3) . . . . ? N3 Co1 N2 C5 -1.3(3) . . . . ? N1 Co1 N2 C5 133.7(3) 8_655 . . . ? O1 Co1 N2 C5 -178.6(3) . . . . ? O4 Co1 N2 C5 92.9(3) 8_655 . . . ? N4 Co1 N2 C2 105.89(14) . . . . ? N3 Co1 N2 C2 -176.31(13) . . . . ? N1 Co1 N2 C2 -41.3(4) 8_655 . . . ? O1 Co1 N2 C2 6.33(13) . . . . ? O4 Co1 N2 C2 -82.18(14) 8_655 . . . ? N4 Co1 N3 C13 177.1(2) . . . . ? N2 Co1 N3 C13 84.1(2) . . . . ? N1 Co1 N3 C13 -87.6(2) 8_655 . . . ? O1 Co1 N3 C13 -149.1(11) . . . . ? O4 Co1 N3 C13 -8.8(2) 8_655 . . . ? N4 Co1 N3 C17 -10.81(15) . . . . ? N2 Co1 N3 C17 -103.81(16) . . . . ? N1 Co1 N3 C17 84.53(16) 8_655 . . . ? O1 Co1 N3 C17 23.0(12) . . . . ? O4 Co1 N3 C17 163.32(15) 8_655 . . . ? N3 Co1 N4 C22 -177.2(2) . . . . ? N2 Co1 N4 C22 -75.5(2) . . . . ? N1 Co1 N4 C22 98.1(2) 8_655 . . . ? O1 Co1 N4 C22 4.6(2) . . . . ? O4 Co1 N4 C22 151.0(3) 8_655 . . . ? N3 Co1 N4 C18 10.27(15) . . . . ? N2 Co1 N4 C18 111.98(16) . . . . ? N1 Co1 N4 C18 -74.39(16) 8_655 . . . ? O1 Co1 N4 C18 -167.90(15) . . . . ? O4 Co1 N4 C18 -21.5(4) 8_655 . . . ? N4 Co1 O1 C1 -101.67(16) . . . . ? N3 Co1 O1 C1 -135.1(11) . . . . ? N2 Co1 O1 C1 -7.76(15) . . . . ? N1 Co1 O1 C1 163.54(16) 8_655 . . . ? O4 Co1 O1 C1 84.49(15) 8_655 . . . ? Co1 O1 C1 O2 -172.98(19) . . . . ? Co1 O1 C1 C2 7.6(3) . . . . ? C5 N2 C2 C3 -0.4(2) . . . . ? Co1 N2 C2 C3 176.72(14) . . . . ? C5 N2 C2 C1 178.04(18) . . . . ? Co1 N2 C2 C1 -4.8(2) . . . . ? O1 C1 C2 N2 -1.9(3) . . . . ? O2 C1 C2 N2 178.6(2) . . . . ? O1 C1 C2 C3 176.1(2) . . . . ? O2 C1 C2 C3 -3.3(4) . . . . ? N2 C2 C3 N1 0.7(2) . . . . ? C1 C2 C3 N1 -177.5(2) . . . . ? N2 C2 C3 C4 175.8(2) . . . . ? C1 C2 C3 C4 -2.3(4) . . . . ? C5 N1 C3 C2 -0.6(2) . . . . ? Co1 N1 C3 C2 159.97(14) 8_665 . . . ? C5 N1 C3 C4 -176.46(19) . . . . ? Co1 N1 C3 C4 -15.9(2) 8_665 . . . ? Co1 O4 C4 O3 -167.82(19) 8_665 . . . ? Co1 O4 C4 C3 11.5(3) 8_665 . . . ? C2 C3 C4 O4 -171.3(2) . . . . ? N1 C3 C4 O4 3.4(3) . . . . ? C2 C3 C4 O3 8.0(4) . . . . ? N1 C3 C4 O3 -177.3(2) . . . . ? C3 N1 C5 N2 0.4(3) . . . . ? Co1 N1 C5 N2 -148.31(19) 8_665 . . . ? C3 N1 C5 C6 -175.46(19) . . . . ? Co1 N1 C5 C6 35.9(4) 8_665 . . . ? C2 N2 C5 N1 0.0(2) . . . . ? Co1 N2 C5 N1 -175.13(18) . . . . ? C2 N2 C5 C6 175.94(19) . . . . ? Co1 N2 C5 C6 0.8(4) . . . . ? N1 C5 C6 C11 49.3(3) . . . . ? N2 C5 C6 C11 -126.1(2) . . . . ? N1 C5 C6 C7 -134.3(2) . . . . ? N2 C5 C6 C7 50.2(3) . . . . ? C7 C6 C11 C10 -3.7(3) . . . . ? C5 C6 C11 C10 172.8(2) . . . . ? C6 C11 C10 C9 1.0(4) . . . . ? C12 O5 C9 C8 -160.4(2) . . . . ? C12 O5 C9 C10 20.0(3) . . . . ? C11 C10 C9 O5 -178.2(2) . . . . ? C11 C10 C9 C8 2.3(4) . . . . ? O5 C9 C8 C7 177.7(2) . . . . ? C10 C9 C8 C7 -2.7(4) . . . . ? C9 C8 C7 C6 -0.1(4) . . . . ? C11 C6 C7 C8 3.3(3) . . . . ? C5 C6 C7 C8 -173.2(2) . . . . ? C17 N3 C13 C14 -1.4(4) . . . . ? Co1 N3 C13 C14 170.5(2) . . . . ? N3 C13 C14 C15 0.5(5) . . . . ? C13 C14 C15 C16 0.9(5) . . . . ? C14 C15 C16 C17 -1.3(5) . . . . ? C13 N3 C17 C16 0.9(3) . . . . ? Co1 N3 C17 C16 -171.80(19) . . . . ? C13 N3 C17 C18 -177.5(2) . . . . ? Co1 N3 C17 C18 9.8(2) . . . . ? C15 C16 C17 N3 0.4(4) . . . . ? C15 C16 C17 C18 178.7(3) . . . . ? C22 N4 C18 C19 0.1(3) . . . . ? Co1 N4 C18 C19 173.17(19) . . . . ? C22 N4 C18 C17 178.4(2) . . . . ? Co1 N4 C18 C17 -8.5(2) . . . . ? N3 C17 C18 N4 -0.9(3) . . . . ? C16 C17 C18 N4 -179.2(2) . . . . ? N3 C17 C18 C19 177.4(2) . . . . ? C16 C17 C18 C19 -0.9(4) . . . . ? N4 C18 C19 C20 -0.4(4) . . . . ? C17 C18 C19 C20 -178.6(2) . . . . ? C18 C19 C20 C21 0.4(4) . . . . ? C19 C20 C21 C22 -0.1(5) . . . . ? C18 N4 C22 C21 0.2(4) . . . . ? Co1 N4 C22 C21 -172.1(2) . . . . ? C20 C21 C22 N4 -0.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O3 0.82 1.67 2.486(2) 174.4 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.598 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.064 # Attachment '- 4.cif' data_p2 #TrackingRef '- 4.cif' _database_code_depnum_ccdc_archive 'CCDC 854850' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 Co N4 O5' _chemical_formula_weight 499.34 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.3055(9) _cell_length_b 16.9232(14) _cell_length_c 12.7590(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.9760(10) _cell_angle_gamma 90.00 _cell_volume 2176.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 0.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8577 _exptl_absorpt_correction_T_max 0.8782 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16244 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3826 _reflns_number_gt 3235 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0404P)^2^+0.6941P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3826 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 Co1 Co 0.52900(3) 0.764655(16) 0.82031(2) 0.02824(10) Uani 1 1 d . . . N1 N 0.51850(16) 0.75053(9) 0.98182(12) 0.0275(4) Uani 1 1 d . . . N2 N 0.49415(16) 0.72681(9) 1.15029(12) 0.0282(4) Uani 1 1 d . . . N3 N 0.66472(17) 0.67293(10) 0.79716(13) 0.0344(4) Uani 1 1 d . . . N4 N 0.71288(17) 0.82557(10) 0.84842(14) 0.0347(4) Uani 1 1 d . . . O1 O 0.40388(15) 0.86282(9) 0.83917(11) 0.0396(4) Uani 1 1 d . . . O2 O 0.28436(16) 0.91067(9) 0.95102(12) 0.0452(4) Uani 1 1 d . . . H2 H 0.2741 0.9014 1.0119 0.068 Uiso 1 1 calc R . . O3 O 0.25865(16) 0.88520(9) 1.13632(12) 0.0458(4) Uani 1 1 d . . . O4 O 0.35736(14) 0.81118(9) 1.27461(11) 0.0379(4) Uani 1 1 d . . . O5 O 0.86765(16) 0.43692(9) 1.04574(16) 0.0589(5) Uani 1 1 d . . . C1 C 0.3695(2) 0.86224(12) 0.92694(16) 0.0325(5) Uani 1 1 d . . . C2 C 0.42936(19) 0.80341(11) 1.00672(15) 0.0274(4) Uani 1 1 d . . . C3 C 0.41384(19) 0.78862(11) 1.10914(15) 0.0274(4) Uani 1 1 d . . . C4 C 0.3387(2) 0.83035(12) 1.17833(16) 0.0322(5) Uani 1 1 d . . . C5 C 0.55425(19) 0.70511(11) 1.07060(14) 0.0263(4) Uani 1 1 d . . . C6 C 0.64270(19) 0.63642(11) 1.07533(15) 0.0282(4) Uani 1 1 d . . . C7 C 0.6023(2) 0.56314(13) 1.10439(19) 0.0443(6) Uani 1 1 d . . . H7A H 0.5244 0.5591 1.1300 0.053 Uiso 1 1 calc R . . C8 C 0.6755(2) 0.49551(14) 1.0962(2) 0.0526(7) Uani 1 1 d . . . H8A H 0.6462 0.4466 1.1152 0.063 Uiso 1 1 calc R . . C9 C 0.7915(2) 0.50131(13) 1.05995(18) 0.0397(5) Uani 1 1 d . . . C10 C 0.8385(2) 0.57449(13) 1.03730(18) 0.0410(5) Uani 1 1 d . . . H10A H 0.9199 0.5786 1.0171 0.049 Uiso 1 1 calc R . . C11 C 0.7642(2) 0.64153(12) 1.04471(17) 0.0358(5) Uani 1 1 d . . . H11A H 0.7959 0.6906 1.0290 0.043 Uiso 1 1 calc R . . C12 C 0.7985(3) 0.36767(15) 1.0047(3) 0.0695(8) Uani 1 1 d . . . H12A H 0.8610 0.3268 0.9980 0.104 Uiso 1 1 calc R . . H12B H 0.7440 0.3787 0.9356 0.104 Uiso 1 1 calc R . . H12C H 0.7436 0.3505 1.0525 0.104 Uiso 1 1 calc R . . C13 C 0.6412(3) 0.59692(14) 0.7751(2) 0.0504(6) Uani 1 1 d . . . H13A H 0.5591 0.5762 0.7802 0.060 Uiso 1 1 calc R . . C14 C 0.7339(3) 0.54700(17) 0.7447(3) 0.0760(9) Uani 1 1 d . . . H14A H 0.7138 0.4941 0.7298 0.091 Uiso 1 1 calc R . . C15 C 0.8533(3) 0.57615(19) 0.7369(3) 0.0818(10) Uani 1 1 d . . . H15A H 0.9158 0.5432 0.7163 0.098 Uiso 1 1 calc R . . C16 C 0.8838(3) 0.65602(17) 0.7599(2) 0.0584(7) Uani 1 1 d . . . C17 C 1.0089(3) 0.6910(2) 0.7561(3) 0.0763(9) Uani 1 1 d . . . H17A H 1.0740 0.6608 0.7346 0.092 Uiso 1 1 calc R . . C18 C 1.0336(3) 0.7672(2) 0.7833(3) 0.0727(9) Uani 1 1 d . . . H18A H 1.1151 0.7891 0.7789 0.087 Uiso 1 1 calc R . . C19 C 0.9368(2) 0.81522(15) 0.8190(2) 0.0516(6) Uani 1 1 d . . . C20 C 0.9582(3) 0.89370(17) 0.8533(3) 0.0752(10) Uani 1 1 d . . . H20A H 1.0406 0.9171 0.8562 0.090 Uiso 1 1 calc R . . C21 C 0.8606(3) 0.93502(16) 0.8819(3) 0.0834(11) Uani 1 1 d . . . H21A H 0.8746 0.9873 0.9039 0.100 Uiso 1 1 calc R . . C22 C 0.7379(3) 0.89974(14) 0.8786(2) 0.0570(7) Uani 1 1 d . . . H22A H 0.6709 0.9294 0.8984 0.068 Uiso 1 1 calc R . . C23 C 0.8121(2) 0.78348(13) 0.81964(17) 0.0356(5) Uani 1 1 d . . . C24 C 0.7856(2) 0.70189(13) 0.79065(17) 0.0371(5) 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 Co1 0.03357(17) 0.03220(17) 0.02099(15) -0.00067(11) 0.01036(11) 0.00079(12) N1 0.0333(9) 0.0296(9) 0.0209(8) -0.0002(6) 0.0089(7) 0.0052(7) N2 0.0331(9) 0.0314(9) 0.0212(8) 0.0006(7) 0.0088(7) 0.0062(7) N3 0.0419(10) 0.0320(10) 0.0297(9) -0.0038(7) 0.0080(8) 0.0018(8) N4 0.0363(10) 0.0310(10) 0.0362(10) -0.0006(8) 0.0058(8) 0.0014(8) O1 0.0522(9) 0.0423(9) 0.0275(8) 0.0087(6) 0.0154(7) 0.0156(7) O2 0.0537(10) 0.0479(9) 0.0379(9) 0.0126(7) 0.0186(7) 0.0257(8) O3 0.0504(10) 0.0500(10) 0.0417(9) 0.0055(7) 0.0207(7) 0.0260(8) O4 0.0423(9) 0.0472(9) 0.0280(8) -0.0003(7) 0.0164(6) 0.0112(7) O5 0.0423(10) 0.0349(9) 0.1045(15) -0.0039(9) 0.0272(10) 0.0125(7) C1 0.0352(11) 0.0332(12) 0.0298(11) 0.0023(9) 0.0086(9) 0.0063(9) C2 0.0308(10) 0.0273(10) 0.0253(10) -0.0016(8) 0.0082(8) 0.0059(8) C3 0.0283(10) 0.0288(10) 0.0259(10) -0.0001(8) 0.0076(8) 0.0055(8) C4 0.0323(11) 0.0362(12) 0.0305(11) -0.0032(9) 0.0122(9) 0.0031(9) C5 0.0305(10) 0.0266(10) 0.0229(10) -0.0012(8) 0.0085(8) 0.0015(8) C6 0.0332(11) 0.0303(11) 0.0221(9) 0.0009(8) 0.0084(8) 0.0058(8) C7 0.0428(13) 0.0377(13) 0.0605(15) 0.0111(11) 0.0296(12) 0.0090(10) C8 0.0526(15) 0.0325(13) 0.0809(19) 0.0126(12) 0.0330(14) 0.0081(11) C9 0.0374(12) 0.0334(12) 0.0497(14) 0.0029(10) 0.0123(10) 0.0118(10) C10 0.0314(12) 0.0404(13) 0.0548(14) -0.0009(11) 0.0174(10) 0.0047(10) C11 0.0371(12) 0.0303(11) 0.0423(12) 0.0020(9) 0.0137(10) 0.0020(9) C12 0.0680(19) 0.0429(16) 0.102(2) -0.0168(15) 0.0276(18) 0.0089(14) C13 0.0561(15) 0.0349(13) 0.0578(16) -0.0109(11) 0.0065(12) -0.0009(11) C14 0.078(2) 0.0471(17) 0.099(2) -0.0349(16) 0.0091(18) 0.0076(15) C15 0.077(2) 0.066(2) 0.108(3) -0.0406(19) 0.0303(19) 0.0171(17) C16 0.0509(15) 0.0641(18) 0.0643(17) -0.0146(14) 0.0214(13) 0.0122(13) C17 0.0511(17) 0.089(2) 0.098(2) -0.011(2) 0.0365(17) 0.0155(17) C18 0.0363(15) 0.091(2) 0.098(2) 0.0173(19) 0.0289(16) 0.0024(15) C19 0.0366(13) 0.0501(16) 0.0668(17) 0.0170(13) 0.0079(12) 0.0008(11) C20 0.0394(15) 0.0500(17) 0.128(3) 0.0245(17) -0.0009(16) -0.0096(13) C21 0.0519(18) 0.0316(15) 0.154(3) 0.0007(17) -0.0081(19) -0.0055(13) C22 0.0470(15) 0.0315(13) 0.087(2) -0.0076(13) 0.0005(13) 0.0035(11) C23 0.0350(12) 0.0371(12) 0.0348(11) 0.0065(9) 0.0078(9) 0.0026(9) C24 0.0395(12) 0.0401(12) 0.0330(11) -0.0029(10) 0.0105(9) 0.0054(10) _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 Co1 N1 2.0994(15) . ? Co1 N4 2.1214(18) . ? Co1 N2 2.1290(16) 4_575 ? Co1 O1 2.1468(14) . ? Co1 N3 2.1505(17) . ? Co1 O4 2.1651(14) 4_575 ? N1 C5 1.355(2) . ? N1 C2 1.366(2) . ? N2 C5 1.347(2) . ? N2 C3 1.369(2) . ? N2 Co1 2.1290(16) 4_576 ? N3 C13 1.328(3) . ? N3 C24 1.357(3) . ? N4 C22 1.323(3) . ? N4 C23 1.358(3) . ? O1 C1 1.243(2) . ? O2 C1 1.284(2) . ? O2 H2 0.8200 . ? O3 C4 1.283(2) . ? O4 C4 1.246(2) . ? O4 Co1 2.1651(14) 4_576 ? O5 C9 1.377(3) . ? O5 C12 1.415(3) . ? C1 C2 1.465(3) . ? C2 C3 1.372(3) . ? C3 C4 1.470(3) . ? C5 C6 1.471(3) . ? C6 C7 1.383(3) . ? C6 C11 1.389(3) . ? C7 C8 1.386(3) . ? C7 H7A 0.9300 . ? C8 C9 1.372(3) . ? C8 H8A 0.9300 . ? C9 C10 1.382(3) . ? C10 C11 1.383(3) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.389(4) . ? C13 H13A 0.9300 . ? C14 C15 1.348(4) . ? C14 H14A 0.9300 . ? C15 C16 1.405(4) . ? C15 H15A 0.9300 . ? C16 C24 1.395(3) . ? C16 C17 1.428(4) . ? C17 C18 1.345(4) . ? C17 H17A 0.9300 . ? C18 C19 1.432(4) . ? C18 H18A 0.9300 . ? C19 C23 1.395(3) . ? C19 C20 1.402(4) . ? C20 C21 1.337(4) . ? C20 H20A 0.9300 . ? C21 C22 1.391(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.441(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 N1 Co1 N4 96.64(7) . . ? N1 Co1 N2 167.34(6) . 4_575 ? N4 Co1 N2 95.46(6) . 4_575 ? N1 Co1 O1 79.84(6) . . ? N4 Co1 O1 98.12(6) . . ? N2 Co1 O1 94.79(6) 4_575 . ? N1 Co1 N3 102.71(6) . . ? N4 Co1 N3 77.90(7) . . ? N2 Co1 N3 83.45(6) 4_575 . ? O1 Co1 N3 175.43(6) . . ? N1 Co1 O4 89.50(6) . 4_575 ? N4 Co1 O4 169.99(6) . 4_575 ? N2 Co1 O4 79.06(6) 4_575 4_575 ? O1 Co1 O4 90.73(6) . 4_575 ? N3 Co1 O4 93.06(6) . 4_575 ? C5 N1 C2 104.86(15) . . ? C5 N1 Co1 145.55(13) . . ? C2 N1 Co1 109.13(12) . . ? C5 N2 C3 104.77(15) . . ? C5 N2 Co1 141.36(13) . 4_576 ? C3 N2 Co1 107.43(12) . 4_576 ? C13 N3 C24 117.8(2) . . ? C13 N3 Co1 129.26(16) . . ? C24 N3 Co1 112.28(14) . . ? C22 N4 C23 117.7(2) . . ? C22 N4 Co1 128.58(16) . . ? C23 N4 Co1 113.31(14) . . ? C1 O1 Co1 112.64(12) . . ? C1 O2 H2 109.5 . . ? C4 O4 Co1 111.74(12) . 4_576 ? C9 O5 C12 116.58(19) . . ? O1 C1 O2 123.18(19) . . ? O1 C1 C2 118.29(17) . . ? O2 C1 C2 118.52(17) . . ? N1 C2 C3 108.59(16) . . ? N1 C2 C1 119.33(16) . . ? C3 C2 C1 132.08(17) . . ? N2 C3 C2 108.90(16) . . ? N2 C3 C4 119.25(17) . . ? C2 C3 C4 131.62(18) . . ? O4 C4 O3 123.70(18) . . ? O4 C4 C3 118.28(18) . . ? O3 C4 C3 118.02(18) . . ? N2 C5 N1 112.87(17) . . ? N2 C5 C6 124.25(17) . . ? N1 C5 C6 122.77(16) . . ? C7 C6 C11 118.04(19) . . ? C7 C6 C5 120.09(18) . . ? C11 C6 C5 121.74(18) . . ? C6 C7 C8 121.4(2) . . ? C6 C7 H7A 119.3 . . ? C8 C7 H7A 119.3 . . ? C9 C8 C7 119.5(2) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 O5 123.2(2) . . ? C8 C9 C10 120.2(2) . . ? O5 C9 C10 116.59(19) . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C10 C11 C6 120.8(2) . . ? C10 C11 H11A 119.6 . . ? C6 C11 H11A 119.6 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 C14 122.8(3) . . ? N3 C13 H13A 118.6 . . ? C14 C13 H13A 118.6 . . ? C15 C14 C13 119.3(3) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C24 C16 C15 116.8(3) . . ? C24 C16 C17 119.4(3) . . ? C15 C16 C17 123.8(3) . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? C17 C18 C19 121.2(2) . . ? C17 C18 H18A 119.4 . . ? C19 C18 H18A 119.4 . . ? C23 C19 C20 116.6(2) . . ? C23 C19 C18 119.2(2) . . ? C20 C19 C18 124.2(3) . . ? C21 C20 C19 120.2(3) . . ? C21 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? C20 C21 C22 119.9(3) . . ? C20 C21 H21A 120.0 . . ? C22 C21 H21A 120.0 . . ? N4 C22 C21 122.5(3) . . ? N4 C22 H22A 118.8 . . ? C21 C22 H22A 118.8 . . ? N4 C23 C19 123.1(2) . . ? N4 C23 C24 117.33(18) . . ? C19 C23 C24 119.5(2) . . ? N3 C24 C16 123.0(2) . . ? N3 C24 C23 117.23(18) . . ? C16 C24 C23 119.7(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 N4 Co1 N1 C5 -86.0(2) . . . . ? N2 Co1 N1 C5 111.2(3) 4_575 . . . ? O1 Co1 N1 C5 176.9(3) . . . . ? N3 Co1 N1 C5 -6.9(3) . . . . ? O4 Co1 N1 C5 86.1(2) 4_575 . . . ? N4 Co1 N1 C2 103.85(13) . . . . ? N2 Co1 N1 C2 -59.0(3) 4_575 . . . ? O1 Co1 N1 C2 6.75(13) . . . . ? N3 Co1 N1 C2 -177.11(13) . . . . ? O4 Co1 N1 C2 -84.08(13) 4_575 . . . ? N1 Co1 N3 C13 83.5(2) . . . . ? N4 Co1 N3 C13 177.7(2) . . . . ? N2 Co1 N3 C13 -85.3(2) 4_575 . . . ? O1 Co1 N3 C13 -152.9(7) . . . . ? O4 Co1 N3 C13 -6.7(2) 4_575 . . . ? N1 Co1 N3 C24 -106.25(14) . . . . ? N4 Co1 N3 C24 -12.08(14) . . . . ? N2 Co1 N3 C24 84.96(14) 4_575 . . . ? O1 Co1 N3 C24 17.4(8) . . . . ? O4 Co1 N3 C24 163.57(14) 4_575 . . . ? N1 Co1 N4 C22 -74.8(2) . . . . ? N2 Co1 N4 C22 101.5(2) 4_575 . . . ? O1 Co1 N4 C22 5.8(2) . . . . ? N3 Co1 N4 C22 -176.4(2) . . . . ? O4 Co1 N4 C22 157.7(3) 4_575 . . . ? N1 Co1 N4 C23 112.90(14) . . . . ? N2 Co1 N4 C23 -70.82(15) 4_575 . . . ? O1 Co1 N4 C23 -166.46(14) . . . . ? N3 Co1 N4 C23 11.27(14) . . . . ? O4 Co1 N4 C23 -14.6(4) 4_575 . . . ? N1 Co1 O1 C1 -7.86(15) . . . . ? N4 Co1 O1 C1 -103.20(15) . . . . ? N2 Co1 O1 C1 160.58(15) 4_575 . . . ? N3 Co1 O1 C1 -132.3(7) . . . . ? O4 Co1 O1 C1 81.50(15) 4_575 . . . ? Co1 O1 C1 O2 -172.84(17) . . . . ? Co1 O1 C1 C2 7.2(2) . . . . ? C5 N1 C2 C3 0.0(2) . . . . ? Co1 N1 C2 C3 174.28(13) . . . . ? C5 N1 C2 C1 -179.85(18) . . . . ? Co1 N1 C2 C1 -5.6(2) . . . . ? O1 C1 C2 N1 -1.1(3) . . . . ? O2 C1 C2 N1 178.89(18) . . . . ? O1 C1 C2 C3 179.0(2) . . . . ? O2 C1 C2 C3 -0.9(4) . . . . ? C5 N2 C3 C2 -1.1(2) . . . . ? Co1 N2 C3 C2 157.29(14) 4_576 . . . ? C5 N2 C3 C4 -176.22(17) . . . . ? Co1 N2 C3 C4 -17.9(2) 4_576 . . . ? N1 C2 C3 N2 0.7(2) . . . . ? C1 C2 C3 N2 -179.5(2) . . . . ? N1 C2 C3 C4 175.0(2) . . . . ? C1 C2 C3 C4 -5.1(4) . . . . ? Co1 O4 C4 O3 -167.45(17) 4_576 . . . ? Co1 O4 C4 C3 11.6(2) 4_576 . . . ? N2 C3 C4 O4 4.6(3) . . . . ? C2 C3 C4 O4 -169.3(2) . . . . ? N2 C3 C4 O3 -176.27(19) . . . . ? C2 C3 C4 O3 9.9(3) . . . . ? C3 N2 C5 N1 1.1(2) . . . . ? Co1 N2 C5 N1 -144.58(17) 4_576 . . . ? C3 N2 C5 C6 -175.07(18) . . . . ? Co1 N2 C5 C6 39.2(3) 4_576 . . . ? C2 N1 C5 N2 -0.7(2) . . . . ? Co1 N1 C5 N2 -171.12(17) . . . . ? C2 N1 C5 C6 175.53(18) . . . . ? Co1 N1 C5 C6 5.1(4) . . . . ? N2 C5 C6 C7 50.9(3) . . . . ? N1 C5 C6 C7 -124.9(2) . . . . ? N2 C5 C6 C11 -133.2(2) . . . . ? N1 C5 C6 C11 50.9(3) . . . . ? C11 C6 C7 C8 -4.5(4) . . . . ? C5 C6 C7 C8 171.5(2) . . . . ? C6 C7 C8 C9 0.9(4) . . . . ? C7 C8 C9 O5 -177.6(2) . . . . ? C7 C8 C9 C10 3.5(4) . . . . ? C12 O5 C9 C8 38.3(4) . . . . ? C12 O5 C9 C10 -142.7(2) . . . . ? C8 C9 C10 C11 -4.1(4) . . . . ? O5 C9 C10 C11 176.9(2) . . . . ? C9 C10 C11 C6 0.4(3) . . . . ? C7 C6 C11 C10 3.9(3) . . . . ? C5 C6 C11 C10 -172.07(19) . . . . ? C24 N3 C13 C14 -0.9(4) . . . . ? Co1 N3 C13 C14 169.0(2) . . . . ? N3 C13 C14 C15 0.0(5) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C14 C15 C16 C24 0.2(5) . . . . ? C14 C15 C16 C17 178.4(3) . . . . ? C24 C16 C17 C18 0.9(5) . . . . ? C15 C16 C17 C18 -177.2(3) . . . . ? C16 C17 C18 C19 1.3(5) . . . . ? C17 C18 C19 C23 -3.6(5) . . . . ? C17 C18 C19 C20 176.8(3) . . . . ? C23 C19 C20 C21 -1.8(4) . . . . ? C18 C19 C20 C21 177.8(3) . . . . ? C19 C20 C21 C22 0.7(5) . . . . ? C23 N4 C22 C21 -0.1(4) . . . . ? Co1 N4 C22 C21 -172.1(2) . . . . ? C20 C21 C22 N4 0.3(5) . . . . ? C22 N4 C23 C19 -1.1(3) . . . . ? Co1 N4 C23 C19 172.11(18) . . . . ? C22 N4 C23 C24 177.8(2) . . . . ? Co1 N4 C23 C24 -9.0(2) . . . . ? C20 C19 C23 N4 2.0(4) . . . . ? C18 C19 C23 N4 -177.5(2) . . . . ? C20 C19 C23 C24 -176.8(2) . . . . ? C18 C19 C23 C24 3.6(4) . . . . ? C13 N3 C24 C16 1.4(3) . . . . ? Co1 N3 C24 C16 -170.08(19) . . . . ? C13 N3 C24 C23 -177.2(2) . . . . ? Co1 N3 C24 C23 11.3(2) . . . . ? C15 C16 C24 N3 -1.1(4) . . . . ? C17 C16 C24 N3 -179.4(2) . . . . ? C15 C16 C24 C23 177.4(2) . . . . ? C17 C16 C24 C23 -0.9(4) . . . . ? N4 C23 C24 N3 -1.7(3) . . . . ? C19 C23 C24 N3 177.2(2) . . . . ? N4 C23 C24 C16 179.7(2) . . . . ? C19 C23 C24 C16 -1.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 1.65 2.471(2) 177.6 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.317 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.045 # Attachment '- 5.cif' data_p3 #TrackingRef '- 5.cif' _database_code_depnum_ccdc_archive 'CCDC 854851' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H19 Cd1.50 N4 O11' _chemical_formula_weight 708.03 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' Cd Cd -0.8075 1.2024 '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 9.0336(8) _cell_length_b 10.1550(9) _cell_length_c 15.4904(13) _cell_angle_alpha 107.6520(10) _cell_angle_beta 97.1680(10) _cell_angle_gamma 105.2960(10) _cell_volume 1273.33(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 702 _exptl_absorpt_coefficient_mu 1.334 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7856 _exptl_absorpt_correction_T_max 0.8352 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11714 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.61 _reflns_number_total 5797 _reflns_number_gt 4658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0331P)^2^+0.2124P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5797 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0693 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cd1 Cd 0.5000 0.0000 0.5000 0.02565(8) Uani 1 2 d S . . Cd2 Cd -0.11754(2) 0.55711(2) 0.587752(14) 0.02650(7) Uani 1 1 d . . . N1 N 0.8672(3) 0.5663(2) 0.73546(15) 0.0263(5) Uani 1 1 d . . . N2 N 0.9221(3) 0.5692(3) 0.87790(16) 0.0376(6) Uani 1 1 d . . . H2 H 0.9610 0.6001 0.9367 0.045 Uiso 1 1 calc R . . N3 N 0.3515(2) 0.1362(2) 0.47158(15) 0.0238(5) Uani 1 1 d . . . N4 N 0.2457(2) 0.3086(2) 0.45934(15) 0.0244(5) Uani 1 1 d . . . O1 O 0.6338(2) 0.1868(2) 0.65067(13) 0.0353(5) Uani 1 1 d . . . O2 O 0.7026(2) 0.3376(2) 0.57362(13) 0.0302(4) Uani 1 1 d . . . O3 O 0.6939(4) 0.1910(3) 0.81591(17) 0.0724(9) Uani 1 1 d . . . H3 H 0.6859 0.1843 0.7613 0.109 Uiso 1 1 calc R . . O4 O 0.8411(4) 0.3490(3) 0.95091(16) 0.0690(8) Uani 1 1 d . . . O5 O 1.2097(3) 1.2592(2) 0.95000(18) 0.0589(7) Uani 1 1 d . . . O6 O 0.2943(2) -0.0372(2) 0.58039(14) 0.0355(5) Uani 1 1 d . . . O7 O 0.1203(3) 0.0615(3) 0.63639(17) 0.0461(6) Uani 1 1 d . . . H7 H 0.0860 0.1277 0.6339 0.069 Uiso 1 1 calc R . . O8 O 0.0147(3) 0.2617(2) 0.62711(15) 0.0410(5) Uani 1 1 d . . . O9 O 0.0460(2) 0.4205(2) 0.55279(14) 0.0359(5) Uani 1 1 d . . . O10 O 0.6666(3) 0.3522(3) 0.15931(16) 0.0549(7) Uani 1 1 d . . . O11 O 0.1217(3) 0.7492(3) 0.64888(18) 0.0588(7) Uani 1 1 d . . . H11A H 0.1794 0.7816 0.6157 0.088 Uiso 1 1 d R . . H11B H 0.0766 0.8142 0.6601 0.088 Uiso 1 1 d R . . C1 C 0.7059(3) 0.3099(3) 0.64653(18) 0.0262(6) Uani 1 1 d . . . C2 C 0.7987(3) 0.4293(3) 0.73612(18) 0.0266(6) Uani 1 1 d . . . C3 C 0.8316(4) 0.4294(3) 0.8246(2) 0.0343(7) Uani 1 1 d . . . C4 C 0.7894(5) 0.3194(4) 0.8689(2) 0.0505(9) Uani 1 1 d . . . C5 C 0.9403(3) 0.6505(3) 0.82292(19) 0.0303(6) Uani 1 1 d . . . C6 C 1.0179(4) 0.8089(3) 0.85686(19) 0.0317(6) Uani 1 1 d . . . C7 C 1.1426(4) 0.8779(3) 0.9338(2) 0.0396(7) Uani 1 1 d . . . H7A H 1.1807 0.8229 0.9638 0.047 Uiso 1 1 calc R . . C8 C 1.2111(4) 1.0283(3) 0.9665(2) 0.0454(8) Uani 1 1 d . . . H8 H 1.2955 1.0742 1.0178 0.054 Uiso 1 1 calc R . . C9 C 1.1523(4) 1.1090(3) 0.9219(2) 0.0416(8) Uani 1 1 d . . . C10 C 1.0285(4) 1.0415(3) 0.8453(2) 0.0473(9) Uani 1 1 d . . . H10 H 0.9908 1.0968 0.8154 0.057 Uiso 1 1 calc R . . C11 C 0.9608(4) 0.8929(3) 0.8131(2) 0.0410(8) Uani 1 1 d . . . H11 H 0.8764 0.8478 0.7619 0.049 Uiso 1 1 calc R . . C12 C 1.3527(5) 1.3300(4) 1.0193(3) 0.0696(12) Uani 1 1 d . . . H12A H 1.3815 1.4334 1.0331 0.104 Uiso 1 1 calc R . . H12B H 1.4347 1.2954 0.9967 0.104 Uiso 1 1 calc R . . H12C H 1.3382 1.3089 1.0746 0.104 Uiso 1 1 calc R . . C13 C 0.2216(3) 0.0517(3) 0.5846(2) 0.0306(6) Uani 1 1 d . . . C14 C 0.2484(3) 0.1472(3) 0.52934(18) 0.0237(6) Uani 1 1 d . . . C15 C 0.1844(3) 0.2530(3) 0.52195(18) 0.0249(6) Uani 1 1 d . . . C16 C 0.0732(3) 0.3151(3) 0.57084(19) 0.0290(6) Uani 1 1 d . . . C17 C 0.3468(3) 0.2353(3) 0.43081(18) 0.0228(5) Uani 1 1 d . . . C18 C 0.4365(3) 0.2669(3) 0.36257(18) 0.0243(6) Uani 1 1 d . . . C19 C 0.4860(3) 0.4084(3) 0.3616(2) 0.0304(6) Uani 1 1 d . . . H19 H 0.4664 0.4827 0.4063 0.036 Uiso 1 1 calc R . . C20 C 0.5635(3) 0.4403(3) 0.2954(2) 0.0362(7) Uani 1 1 d . . . H20 H 0.5971 0.5359 0.2966 0.043 Uiso 1 1 calc R . . C21 C 0.5914(4) 0.3318(4) 0.2277(2) 0.0375(7) Uani 1 1 d . . . C22 C 0.5438(4) 0.1901(4) 0.2275(2) 0.0422(8) Uani 1 1 d . . . H22 H 0.5629 0.1162 0.1822 0.051 Uiso 1 1 calc R . . C23 C 0.4678(4) 0.1583(3) 0.2950(2) 0.0342(7) Uani 1 1 d . . . H23 H 0.4375 0.0633 0.2948 0.041 Uiso 1 1 calc R . . C24 C 0.7276(5) 0.4969(5) 0.1601(3) 0.0651(11) Uani 1 1 d . . . H24A H 0.7778 0.4957 0.1089 0.098 Uiso 1 1 calc R . . H24B H 0.8031 0.5559 0.2173 0.098 Uiso 1 1 calc R . . H24C H 0.6432 0.5369 0.1546 0.098 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 Cd1 0.03016(15) 0.02756(15) 0.02427(15) 0.00951(12) 0.00495(11) 0.01736(12) Cd2 0.03273(12) 0.02929(12) 0.02814(11) 0.01621(9) 0.01173(9) 0.01767(9) N1 0.0311(12) 0.0238(12) 0.0224(11) 0.0075(10) 0.0040(10) 0.0077(10) N2 0.0547(17) 0.0269(13) 0.0210(12) 0.0076(10) -0.0021(11) 0.0024(12) N3 0.0242(11) 0.0248(12) 0.0264(12) 0.0105(10) 0.0054(9) 0.0125(10) N4 0.0263(11) 0.0250(12) 0.0266(12) 0.0122(10) 0.0069(9) 0.0118(10) O1 0.0448(12) 0.0230(10) 0.0299(11) 0.0087(9) 0.0012(9) 0.0018(9) O2 0.0362(11) 0.0295(10) 0.0222(9) 0.0081(8) 0.0027(8) 0.0091(9) O3 0.117(2) 0.0336(14) 0.0384(14) 0.0179(12) -0.0123(15) -0.0149(15) O4 0.111(2) 0.0434(15) 0.0328(13) 0.0203(12) -0.0087(14) -0.0033(15) O5 0.0721(18) 0.0239(12) 0.0610(16) 0.0106(11) -0.0097(14) -0.0003(12) O6 0.0438(12) 0.0331(11) 0.0453(13) 0.0240(10) 0.0174(10) 0.0224(10) O7 0.0566(15) 0.0522(15) 0.0631(15) 0.0416(13) 0.0377(13) 0.0354(12) O8 0.0483(13) 0.0557(14) 0.0471(13) 0.0344(12) 0.0286(11) 0.0345(12) O9 0.0460(12) 0.0421(12) 0.0422(12) 0.0255(10) 0.0229(10) 0.0318(10) O10 0.0664(16) 0.0735(18) 0.0452(14) 0.0336(13) 0.0344(13) 0.0305(14) O11 0.0457(14) 0.0606(17) 0.0697(17) 0.0410(14) 0.0043(13) -0.0008(12) C1 0.0281(14) 0.0254(14) 0.0247(14) 0.0078(11) 0.0042(11) 0.0098(12) C2 0.0338(15) 0.0217(13) 0.0247(14) 0.0087(11) 0.0061(12) 0.0088(12) C3 0.0479(18) 0.0233(14) 0.0258(15) 0.0094(12) 0.0014(13) 0.0042(13) C4 0.075(3) 0.0313(18) 0.0335(18) 0.0153(15) -0.0045(17) 0.0014(17) C5 0.0379(16) 0.0246(14) 0.0253(14) 0.0085(12) 0.0041(12) 0.0070(13) C6 0.0421(17) 0.0254(15) 0.0254(14) 0.0095(12) 0.0067(13) 0.0066(13) C7 0.050(2) 0.0289(16) 0.0330(16) 0.0123(13) -0.0037(14) 0.0063(15) C8 0.051(2) 0.0329(18) 0.0365(18) 0.0092(15) -0.0073(15) 0.0001(16) C9 0.052(2) 0.0226(15) 0.0404(18) 0.0079(14) 0.0035(15) 0.0022(14) C10 0.065(2) 0.0292(17) 0.0420(19) 0.0140(15) -0.0047(17) 0.0115(16) C11 0.0499(19) 0.0299(16) 0.0332(17) 0.0074(14) -0.0069(14) 0.0080(15) C12 0.070(3) 0.033(2) 0.080(3) 0.011(2) -0.002(2) -0.0077(19) C13 0.0324(15) 0.0279(15) 0.0354(16) 0.0147(13) 0.0076(13) 0.0119(13) C14 0.0248(13) 0.0243(14) 0.0262(14) 0.0111(11) 0.0064(11) 0.0115(11) C15 0.0256(14) 0.0259(14) 0.0276(14) 0.0120(12) 0.0077(11) 0.0116(12) C16 0.0302(15) 0.0338(16) 0.0303(15) 0.0145(13) 0.0075(12) 0.0176(13) C17 0.0245(13) 0.0233(13) 0.0240(13) 0.0101(11) 0.0053(11) 0.0108(11) C18 0.0213(13) 0.0281(14) 0.0259(13) 0.0118(12) 0.0040(11) 0.0096(11) C19 0.0328(15) 0.0291(15) 0.0308(15) 0.0101(12) 0.0089(12) 0.0120(13) C20 0.0365(17) 0.0395(18) 0.0387(17) 0.0225(15) 0.0100(14) 0.0110(14) C21 0.0352(16) 0.054(2) 0.0328(16) 0.0209(15) 0.0140(13) 0.0201(15) C22 0.051(2) 0.047(2) 0.0341(17) 0.0100(15) 0.0184(15) 0.0262(17) C23 0.0424(17) 0.0317(16) 0.0355(16) 0.0149(13) 0.0133(14) 0.0176(14) C24 0.060(2) 0.085(3) 0.059(3) 0.041(2) 0.026(2) 0.011(2) _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 Cd1 N3 2.260(2) 2_656 ? Cd1 N3 2.260(2) . ? Cd1 O6 2.3742(19) . ? Cd1 O6 2.3742(19) 2_656 ? Cd1 O1 2.4305(19) . ? Cd1 O1 2.4305(19) 2_656 ? Cd2 N4 2.227(2) 2_566 ? Cd2 N1 2.284(2) 1_455 ? Cd2 O9 2.2856(18) . ? Cd2 O2 2.3153(19) 1_455 ? Cd2 O11 2.349(2) . ? Cd2 O9 2.4048(19) 2_566 ? N1 C5 1.334(3) . ? N1 C2 1.370(3) . ? N1 Cd2 2.284(2) 1_655 ? N2 C5 1.350(3) . ? N2 C3 1.369(4) . ? N2 H2 0.8600 . ? N3 C17 1.347(3) . ? N3 C14 1.372(3) . ? N4 C17 1.358(3) . ? N4 C15 1.367(3) . ? N4 Cd2 2.227(2) 2_566 ? O1 C1 1.273(3) . ? O2 C1 1.242(3) . ? O2 Cd2 2.3153(19) 1_655 ? O3 C4 1.303(4) . ? O3 H3 0.8200 . ? O4 C4 1.212(4) . ? O5 C9 1.382(3) . ? O5 C12 1.426(4) . ? O6 C13 1.241(3) . ? O7 C13 1.294(3) . ? O7 H7 0.8200 . ? O8 C16 1.258(3) . ? O9 C16 1.261(3) . ? O9 Cd2 2.4048(19) 2_566 ? O10 C21 1.366(3) . ? O10 C24 1.423(4) . ? O11 H11A 0.8500 . ? O11 H11B 0.8501 . ? C1 C2 1.500(4) . ? C2 C3 1.366(4) . ? C3 C4 1.473(4) . ? C5 C6 1.469(4) . ? C6 C7 1.386(4) . ? C6 C11 1.395(4) . ? C7 C8 1.388(4) . ? C7 H7A 0.9300 . ? C8 C9 1.383(4) . ? C8 H8 0.9300 . ? C9 C10 1.378(5) . ? C10 C11 1.372(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.470(4) . ? C14 C15 1.374(3) . ? C15 C16 1.488(3) . ? C17 C18 1.470(4) . ? C18 C23 1.389(4) . ? C18 C19 1.393(4) . ? C19 C20 1.381(4) . ? C19 H19 0.9300 . ? C20 C21 1.375(4) . ? C20 H20 0.9300 . ? C21 C22 1.387(4) . ? C22 C23 1.391(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 N3 Cd1 N3 180.00(11) 2_656 . ? N3 Cd1 O6 106.22(7) 2_656 . ? N3 Cd1 O6 73.78(7) . . ? N3 Cd1 O6 73.78(7) 2_656 2_656 ? N3 Cd1 O6 106.22(7) . 2_656 ? O6 Cd1 O6 180.0 . 2_656 ? N3 Cd1 O1 89.34(7) 2_656 . ? N3 Cd1 O1 90.66(7) . . ? O6 Cd1 O1 81.03(7) . . ? O6 Cd1 O1 98.97(7) 2_656 . ? N3 Cd1 O1 90.66(7) 2_656 2_656 ? N3 Cd1 O1 89.34(7) . 2_656 ? O6 Cd1 O1 98.97(7) . 2_656 ? O6 Cd1 O1 81.03(7) 2_656 2_656 ? O1 Cd1 O1 180.0 . 2_656 ? N4 Cd2 N1 112.07(8) 2_566 1_455 ? N4 Cd2 O9 145.39(7) 2_566 . ? N1 Cd2 O9 102.30(7) 1_455 . ? N4 Cd2 O2 109.00(7) 2_566 1_455 ? N1 Cd2 O2 73.69(7) 1_455 1_455 ? O9 Cd2 O2 83.95(7) . 1_455 ? N4 Cd2 O11 93.74(8) 2_566 . ? N1 Cd2 O11 89.05(8) 1_455 . ? O9 Cd2 O11 82.57(9) . . ? O2 Cd2 O11 155.25(7) 1_455 . ? N4 Cd2 O9 71.71(7) 2_566 2_566 ? N1 Cd2 O9 168.05(8) 1_455 2_566 ? O9 Cd2 O9 73.80(7) . 2_566 ? O2 Cd2 O9 116.48(7) 1_455 2_566 ? O11 Cd2 O9 79.29(8) . 2_566 ? C5 N1 C2 106.8(2) . . ? C5 N1 Cd2 139.24(19) . 1_655 ? C2 N1 Cd2 110.30(16) . 1_655 ? C5 N2 C3 108.7(2) . . ? C5 N2 H2 125.6 . . ? C3 N2 H2 125.6 . . ? C17 N3 C14 105.2(2) . . ? C17 N3 Cd1 141.72(17) . . ? C14 N3 Cd1 111.33(16) . . ? C17 N4 C15 105.2(2) . . ? C17 N4 Cd2 138.64(17) . 2_566 ? C15 N4 Cd2 114.14(16) . 2_566 ? C1 O1 Cd1 113.96(17) . . ? C1 O2 Cd2 114.71(17) . 1_655 ? C4 O3 H3 109.5 . . ? C9 O5 C12 116.7(3) . . ? C13 O6 Cd1 112.35(17) . . ? C13 O7 H7 109.5 . . ? C16 O9 Cd2 137.12(18) . . ? C16 O9 Cd2 113.47(17) . 2_566 ? Cd2 O9 Cd2 106.20(7) . 2_566 ? C21 O10 C24 118.1(3) . . ? Cd2 O11 H11A 123.9 . . ? Cd2 O11 H11B 93.3 . . ? H11A O11 H11B 97.3 . . ? O2 C1 O1 124.3(3) . . ? O2 C1 C2 118.3(2) . . ? O1 C1 C2 117.4(2) . . ? C3 C2 N1 109.4(2) . . ? C3 C2 C1 131.5(3) . . ? N1 C2 C1 119.1(2) . . ? C2 C3 N2 105.6(2) . . ? C2 C3 C4 134.8(3) . . ? N2 C3 C4 119.5(3) . . ? O4 C4 O3 122.5(3) . . ? O4 C4 C3 120.8(3) . . ? O3 C4 C3 116.8(3) . . ? N1 C5 N2 109.4(2) . . ? N1 C5 C6 126.0(3) . . ? N2 C5 C6 124.4(2) . . ? C7 C6 C11 119.1(3) . . ? C7 C6 C5 121.5(3) . . ? C11 C6 C5 119.3(3) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C9 C8 C7 119.1(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 O5 115.5(3) . . ? C10 C9 C8 120.8(3) . . ? O5 C9 C8 123.7(3) . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C6 120.3(3) . . ? C10 C11 H11 119.8 . . ? C6 C11 H11 119.8 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O6 C13 O7 121.1(3) . . ? O6 C13 C14 120.1(2) . . ? O7 C13 C14 118.8(2) . . ? N3 C14 C15 108.6(2) . . ? N3 C14 C13 120.1(2) . . ? C15 C14 C13 131.3(2) . . ? N4 C15 C14 108.6(2) . . ? N4 C15 C16 119.4(2) . . ? C14 C15 C16 132.0(2) . . ? O8 C16 O9 124.6(3) . . ? O8 C16 C15 119.1(2) . . ? O9 C16 C15 116.3(2) . . ? N3 C17 N4 112.4(2) . . ? N3 C17 C18 126.8(2) . . ? N4 C17 C18 120.7(2) . . ? C23 C18 C19 118.0(3) . . ? C23 C18 C17 122.1(2) . . ? C19 C18 C17 119.8(2) . . ? C20 C19 C18 121.2(3) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? O10 C21 C20 124.8(3) . . ? O10 C21 C22 115.8(3) . . ? C20 C21 C22 119.4(3) . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C18 C23 C22 120.8(3) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? O10 C24 H24A 109.5 . . ? O10 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O10 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? 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 N3 Cd1 N3 C17 -36(100) 2_656 . . . ? O6 Cd1 N3 C17 174.1(3) . . . . ? O6 Cd1 N3 C17 -5.9(3) 2_656 . . . ? O1 Cd1 N3 C17 93.6(3) . . . . ? O1 Cd1 N3 C17 -86.4(3) 2_656 . . . ? N3 Cd1 N3 C14 163(100) 2_656 . . . ? O6 Cd1 N3 C14 12.44(17) . . . . ? O6 Cd1 N3 C14 -167.56(17) 2_656 . . . ? O1 Cd1 N3 C14 -68.03(18) . . . . ? O1 Cd1 N3 C14 111.97(18) 2_656 . . . ? N3 Cd1 O1 C1 120.16(19) 2_656 . . . ? N3 Cd1 O1 C1 -59.84(19) . . . . ? O6 Cd1 O1 C1 -133.30(19) . . . . ? O6 Cd1 O1 C1 46.70(19) 2_656 . . . ? O1 Cd1 O1 C1 39(100) 2_656 . . . ? N3 Cd1 O6 C13 167.5(2) 2_656 . . . ? N3 Cd1 O6 C13 -12.5(2) . . . . ? O6 Cd1 O6 C13 -62(100) 2_656 . . . ? O1 Cd1 O6 C13 80.8(2) . . . . ? O1 Cd1 O6 C13 -99.2(2) 2_656 . . . ? N4 Cd2 O9 C16 -152.4(3) 2_566 . . . ? N1 Cd2 O9 C16 34.4(3) 1_455 . . . ? O2 Cd2 O9 C16 -37.4(3) 1_455 . . . ? O11 Cd2 O9 C16 121.8(3) . . . . ? O9 Cd2 O9 C16 -157.3(3) 2_566 . . . ? N4 Cd2 O9 Cd2 4.85(18) 2_566 . . 2_566 ? N1 Cd2 O9 Cd2 -168.34(8) 1_455 . . 2_566 ? O2 Cd2 O9 Cd2 119.85(9) 1_455 . . 2_566 ? O11 Cd2 O9 Cd2 -80.95(9) . . . 2_566 ? O9 Cd2 O9 Cd2 0.0 2_566 . . 2_566 ? Cd2 O2 C1 O1 -169.2(2) 1_655 . . . ? Cd2 O2 C1 C2 11.7(3) 1_655 . . . ? Cd1 O1 C1 O2 4.0(3) . . . . ? Cd1 O1 C1 C2 -176.89(17) . . . . ? C5 N1 C2 C3 -0.7(3) . . . . ? Cd2 N1 C2 C3 162.2(2) 1_655 . . . ? C5 N1 C2 C1 179.5(2) . . . . ? Cd2 N1 C2 C1 -17.6(3) 1_655 . . . ? O2 C1 C2 C3 -175.4(3) . . . . ? O1 C1 C2 C3 5.5(4) . . . . ? O2 C1 C2 N1 4.4(4) . . . . ? O1 C1 C2 N1 -174.8(2) . . . . ? N1 C2 C3 N2 -0.2(3) . . . . ? C1 C2 C3 N2 179.6(3) . . . . ? N1 C2 C3 C4 178.4(4) . . . . ? C1 C2 C3 C4 -1.9(6) . . . . ? C5 N2 C3 C2 1.0(3) . . . . ? C5 N2 C3 C4 -177.8(3) . . . . ? C2 C3 C4 O4 177.4(4) . . . . ? N2 C3 C4 O4 -4.2(6) . . . . ? C2 C3 C4 O3 -3.2(6) . . . . ? N2 C3 C4 O3 175.3(3) . . . . ? C2 N1 C5 N2 1.3(3) . . . . ? Cd2 N1 C5 N2 -153.7(2) 1_655 . . . ? C2 N1 C5 C6 -174.1(3) . . . . ? Cd2 N1 C5 C6 30.9(5) 1_655 . . . ? C3 N2 C5 N1 -1.5(3) . . . . ? C3 N2 C5 C6 174.0(3) . . . . ? N1 C5 C6 C7 -152.2(3) . . . . ? N2 C5 C6 C7 33.1(5) . . . . ? N1 C5 C6 C11 30.6(5) . . . . ? N2 C5 C6 C11 -144.2(3) . . . . ? C11 C6 C7 C8 -0.7(5) . . . . ? C5 C6 C7 C8 -178.0(3) . . . . ? C6 C7 C8 C9 0.6(5) . . . . ? C12 O5 C9 C10 -170.3(3) . . . . ? C12 O5 C9 C8 10.4(5) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? C7 C8 C9 O5 178.5(3) . . . . ? O5 C9 C10 C11 -178.5(3) . . . . ? C8 C9 C10 C11 0.8(6) . . . . ? C9 C10 C11 C6 -0.8(5) . . . . ? C7 C6 C11 C10 0.8(5) . . . . ? C5 C6 C11 C10 178.1(3) . . . . ? Cd1 O6 C13 O7 -170.4(2) . . . . ? Cd1 O6 C13 C14 10.3(3) . . . . ? C17 N3 C14 C15 -0.1(3) . . . . ? Cd1 N3 C14 C15 168.25(17) . . . . ? C17 N3 C14 C13 179.0(2) . . . . ? Cd1 N3 C14 C13 -12.7(3) . . . . ? O6 C13 C14 N3 1.3(4) . . . . ? O7 C13 C14 N3 -178.0(3) . . . . ? O6 C13 C14 C15 -179.8(3) . . . . ? O7 C13 C14 C15 0.9(5) . . . . ? C17 N4 C15 C14 -0.4(3) . . . . ? Cd2 N4 C15 C14 166.35(17) 2_566 . . . ? C17 N4 C15 C16 177.1(2) . . . . ? Cd2 N4 C15 C16 -16.1(3) 2_566 . . . ? N3 C14 C15 N4 0.3(3) . . . . ? C13 C14 C15 N4 -178.6(3) . . . . ? N3 C14 C15 C16 -176.8(3) . . . . ? C13 C14 C15 C16 4.3(5) . . . . ? Cd2 O9 C16 O8 -6.9(5) . . . . ? Cd2 O9 C16 O8 -163.1(2) 2_566 . . . ? Cd2 O9 C16 C15 173.87(19) . . . . ? Cd2 O9 C16 C15 17.7(3) 2_566 . . . ? N4 C15 C16 O8 178.7(3) . . . . ? C14 C15 C16 O8 -4.5(5) . . . . ? N4 C15 C16 O9 -2.1(4) . . . . ? C14 C15 C16 O9 174.8(3) . . . . ? C14 N3 C17 N4 -0.2(3) . . . . ? Cd1 N3 C17 N4 -162.5(2) . . . . ? C14 N3 C17 C18 179.9(3) . . . . ? Cd1 N3 C17 C18 17.6(5) . . . . ? C15 N4 C17 N3 0.4(3) . . . . ? Cd2 N4 C17 N3 -161.2(2) 2_566 . . . ? C15 N4 C17 C18 -179.7(2) . . . . ? Cd2 N4 C17 C18 18.7(4) 2_566 . . . ? N3 C17 C18 C23 36.6(4) . . . . ? N4 C17 C18 C23 -143.3(3) . . . . ? N3 C17 C18 C19 -146.8(3) . . . . ? N4 C17 C18 C19 33.4(4) . . . . ? C23 C18 C19 C20 0.1(4) . . . . ? C17 C18 C19 C20 -176.7(3) . . . . ? C18 C19 C20 C21 1.1(4) . . . . ? C24 O10 C21 C20 3.1(5) . . . . ? C24 O10 C21 C22 -175.7(3) . . . . ? C19 C20 C21 O10 179.9(3) . . . . ? C19 C20 C21 C22 -1.4(5) . . . . ? O10 C21 C22 C23 179.3(3) . . . . ? C20 C21 C22 C23 0.4(5) . . . . ? C19 C18 C23 C22 -1.0(4) . . . . ? C17 C18 C23 C22 175.7(3) . . . . ? C21 C22 C23 C18 0.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.718 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.081 # Attachment '- 6.cif' data_p4 #TrackingRef '- 6.cif' _database_code_depnum_ccdc_archive 'CCDC 854852' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H26 Co1.50 N5 O12' _chemical_formula_weight 724.94 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.821(3) _cell_length_b 7.4740(13) _cell_length_c 20.988(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.716(2) _cell_angle_gamma 90.00 _cell_volume 2992.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3937 _cell_measurement_theta_min 2.5083 _cell_measurement_theta_max 26.1641 _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1486 _exptl_absorpt_coefficient_mu 0.916 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8309 _exptl_absorpt_correction_T_max 0.8599 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15909 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 26.35 _reflns_number_total 6074 _reflns_number_gt 4653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0576P)^2^+1.0300P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6074 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 Co1 Co 0.355836(19) 0.22599(5) 0.227178(17) 0.02250(12) Uani 1 1 d . . . Co2 Co 0.5000 0.5000 0.5000 0.02235(14) Uani 1 2 d S . . N1 N 0.22332(12) 0.5762(3) 0.34185(10) 0.0232(5) Uani 1 1 d . . . N2 N 0.31294(12) 0.4788(3) 0.42052(10) 0.0247(5) Uani 1 1 d . . . H2A H 0.3389 0.4534 0.4594 0.030 Uiso 1 1 calc R . . N3 N 0.40676(12) -0.0776(3) 0.37013(10) 0.0248(5) Uani 1 1 d . . . H3A H 0.3757 -0.0005 0.3508 0.030 Uiso 1 1 calc R . . N4 N 0.46744(12) -0.2624(3) 0.44558(10) 0.0240(5) Uani 1 1 d . . . N5 N 0.42037(13) 0.3434(3) 0.17275(11) 0.0313(6) Uani 1 1 d . . . O1 O 0.41702(10) 0.3343(3) 0.31372(9) 0.0300(5) Uani 1 1 d . . . O2 O 0.44064(10) 0.3541(3) 0.42288(9) 0.0297(5) Uani 1 1 d . . . O3 O 0.29378(10) 0.4494(3) 0.20849(9) 0.0301(5) Uani 1 1 d . . . O4 O 0.20254(9) 0.6136(3) 0.21280(8) 0.0251(4) Uani 1 1 d . . . O5 O 0.42069(11) -0.0059(3) 0.24048(9) 0.0341(5) Uani 1 1 d . . . O6 O 0.51050(13) -0.1888(4) 0.25810(11) 0.0495(7) Uani 1 1 d . . . H6 H 0.5313 -0.2584 0.2870 0.074 Uiso 1 1 calc R . . O7 O 0.58177(11) -0.3807(3) 0.34658(10) 0.0413(6) Uani 1 1 d . . . O8 O 0.57813(10) -0.4710(3) 0.44697(9) 0.0298(5) Uani 1 1 d . . . O9 O 0.08068(13) 0.6063(4) 0.58248(11) 0.0580(7) Uani 1 1 d . . . O10 O 0.27766(13) 0.0757(4) 0.61924(11) 0.0525(7) Uani 1 1 d . . . O11 O 0.29155(19) 0.8242(5) 0.72991(16) 0.0884(10) Uani 1 1 d . . . H1W H 0.2609 0.8561 0.7492 0.133 Uiso 1 1 d R . . H2W H 0.2978 0.9161 0.7083 0.133 Uiso 1 1 d R . . O12 O 0.68911(17) 0.5358(5) 0.28056(16) 0.0899(11) Uani 1 1 d . . . H3W H 0.6674 0.5445 0.3102 0.135 Uiso 1 1 d R . . H4W H 0.6950 0.4240 0.2771 0.135 Uiso 1 1 d R . . C1 C 0.40143(14) 0.3784(4) 0.36531(13) 0.0232(6) Uani 1 1 d . . . C2 C 0.33197(14) 0.4591(4) 0.36273(12) 0.0229(6) Uani 1 1 d . . . C3 C 0.27519(14) 0.5201(4) 0.31409(13) 0.0226(6) Uani 1 1 d . . . C4 C 0.25804(14) 0.5264(4) 0.24048(13) 0.0221(6) Uani 1 1 d . . . C5 C 0.24688(15) 0.5443(4) 0.40670(13) 0.0253(6) Uani 1 1 d . . . C6 C 0.20624(15) 0.5636(4) 0.45475(13) 0.0265(6) Uani 1 1 d . . . C7 C 0.13449(16) 0.5292(4) 0.43451(15) 0.0347(7) Uani 1 1 d . . . H7A H 0.1137 0.4953 0.3910 0.042 Uiso 1 1 calc R . . C8 C 0.09426(17) 0.5446(5) 0.47779(15) 0.0411(8) Uani 1 1 d . . . H8A H 0.0464 0.5217 0.4637 0.049 Uiso 1 1 calc R . . C9 C 0.12506(17) 0.5946(5) 0.54300(15) 0.0373(7) Uani 1 1 d . . . C10 C 0.19600(17) 0.6274(5) 0.56405(14) 0.0378(8) Uani 1 1 d . . . H10A H 0.2167 0.6606 0.6077 0.045 Uiso 1 1 calc R . . C11 C 0.23650(16) 0.6108(4) 0.51980(14) 0.0329(7) Uani 1 1 d . . . H11A H 0.2845 0.6317 0.5341 0.039 Uiso 1 1 calc R . . C12 C 0.1103(2) 0.6336(7) 0.65195(18) 0.0753(14) Uani 1 1 d . . . H12A H 0.0734 0.6394 0.6736 0.113 Uiso 1 1 calc R . . H12B H 0.1363 0.7436 0.6590 0.113 Uiso 1 1 calc R . . H12C H 0.1411 0.5360 0.6699 0.113 Uiso 1 1 calc R . . C13 C 0.46107(16) -0.1112(4) 0.27669(13) 0.0290(6) Uani 1 1 d . . . C14 C 0.45526(14) -0.1539(4) 0.34358(13) 0.0241(6) Uani 1 1 d . . . C15 C 0.49309(15) -0.2679(4) 0.39110(13) 0.0246(6) Uani 1 1 d . . . C16 C 0.55557(15) -0.3823(4) 0.39500(13) 0.0272(6) Uani 1 1 d . . . C17 C 0.41554(14) -0.1432(4) 0.43219(12) 0.0229(6) Uani 1 1 d . . . C18 C 0.37751(15) -0.0820(4) 0.47844(13) 0.0253(6) Uani 1 1 d . . . C19 C 0.31417(16) 0.0080(4) 0.45825(15) 0.0333(7) Uani 1 1 d . . . H19A H 0.2945 0.0298 0.4134 0.040 Uiso 1 1 calc R . . C20 C 0.27978(17) 0.0658(4) 0.50363(15) 0.0377(8) Uani 1 1 d . . . H20A H 0.2377 0.1280 0.4895 0.045 Uiso 1 1 calc R . . C21 C 0.30828(17) 0.0307(4) 0.57008(15) 0.0351(7) Uani 1 1 d . . . C22 C 0.37213(17) -0.0563(4) 0.59137(14) 0.0354(7) Uani 1 1 d . . . H22A H 0.3916 -0.0774 0.6363 0.042 Uiso 1 1 calc R . . C23 C 0.40672(16) -0.1113(4) 0.54665(14) 0.0300(7) Uani 1 1 d . . . H23A H 0.4498 -0.1685 0.5614 0.036 Uiso 1 1 calc R . . C24 C 0.2087(2) 0.1446(7) 0.6001(2) 0.0700(13) Uani 1 1 d . . . H24A H 0.1934 0.1702 0.6388 0.105 Uiso 1 1 calc R . . H24B H 0.1778 0.0580 0.5734 0.105 Uiso 1 1 calc R . . H24C H 0.2078 0.2525 0.5751 0.105 Uiso 1 1 calc R . . C25 C 0.4885(2) 0.3088(7) 0.1866(2) 0.0754(10) Uani 1 1 d . . . H25A H 0.5079 0.2324 0.2217 0.090 Uiso 1 1 calc R . . C26 C 0.5315(2) 0.3787(7) 0.1524(2) 0.0754(10) Uani 1 1 d . . . H26A H 0.5790 0.3502 0.1638 0.090 Uiso 1 1 calc R . . C27 C 0.5035(3) 0.4920(7) 0.1005(2) 0.0755(14) Uani 1 1 d . . . H27A H 0.5313 0.5397 0.0755 0.091 Uiso 1 1 calc R . . C28 C 0.4348(3) 0.5329(6) 0.0865(2) 0.0734(14) Uani 1 1 d . . . H28A H 0.4147 0.6114 0.0523 0.088 Uiso 1 1 calc R . . C29 C 0.3950(2) 0.4563(5) 0.12384(19) 0.0570(11) Uani 1 1 d . . . H29A H 0.3477 0.4858 0.1140 0.068 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 Co1 0.0213(2) 0.0282(2) 0.01822(19) 0.00080(15) 0.00577(15) 0.00026(16) Co2 0.0216(3) 0.0276(3) 0.0165(3) 0.0022(2) 0.0028(2) 0.0015(2) N1 0.0232(12) 0.0276(13) 0.0201(11) -0.0014(9) 0.0082(10) -0.0002(10) N2 0.0253(12) 0.0321(13) 0.0152(11) 0.0014(9) 0.0030(9) 0.0025(10) N3 0.0273(12) 0.0262(13) 0.0207(11) 0.0037(9) 0.0062(10) 0.0061(10) N4 0.0250(12) 0.0288(13) 0.0182(11) 0.0025(9) 0.0058(10) 0.0042(10) N5 0.0322(14) 0.0355(15) 0.0286(13) -0.0007(11) 0.0121(11) -0.0030(12) O1 0.0228(10) 0.0446(13) 0.0223(10) -0.0064(9) 0.0059(8) -0.0015(9) O2 0.0278(10) 0.0345(12) 0.0217(10) -0.0022(8) -0.0020(8) 0.0036(9) O3 0.0334(11) 0.0372(12) 0.0215(10) 0.0046(8) 0.0105(9) 0.0128(10) O4 0.0231(10) 0.0325(11) 0.0194(9) 0.0006(8) 0.0050(8) 0.0043(9) O5 0.0404(12) 0.0394(12) 0.0239(10) 0.0102(9) 0.0114(9) 0.0130(10) O6 0.0565(16) 0.0666(17) 0.0343(13) 0.0221(11) 0.0278(12) 0.0341(13) O7 0.0399(13) 0.0563(15) 0.0354(12) 0.0154(11) 0.0235(10) 0.0195(11) O8 0.0256(10) 0.0363(12) 0.0279(11) 0.0071(9) 0.0078(9) 0.0068(9) O9 0.0477(15) 0.095(2) 0.0416(14) -0.0098(14) 0.0288(12) -0.0041(15) O10 0.0532(15) 0.0708(18) 0.0433(14) -0.0111(12) 0.0296(12) 0.0070(13) O11 0.107(3) 0.083(2) 0.088(2) 0.0042(18) 0.047(2) 0.004(2) O12 0.088(2) 0.108(3) 0.093(2) 0.003(2) 0.056(2) 0.022(2) C1 0.0233(14) 0.0215(14) 0.0226(14) 0.0000(11) 0.0025(11) -0.0028(12) C2 0.0260(14) 0.0244(14) 0.0181(13) -0.0020(11) 0.0055(11) -0.0035(12) C3 0.0232(14) 0.0252(15) 0.0201(13) 0.0014(11) 0.0070(11) 0.0014(11) C4 0.0215(14) 0.0223(14) 0.0226(14) 0.0011(11) 0.0061(11) -0.0023(12) C5 0.0251(14) 0.0277(15) 0.0222(14) 0.0001(11) 0.0047(12) 0.0002(12) C6 0.0307(15) 0.0275(15) 0.0218(14) 0.0001(11) 0.0081(12) 0.0004(13) C7 0.0324(17) 0.0455(19) 0.0257(15) -0.0016(13) 0.0069(13) -0.0043(15) C8 0.0302(17) 0.061(2) 0.0339(17) -0.0015(16) 0.0124(14) -0.0032(16) C9 0.0372(18) 0.0436(19) 0.0365(17) -0.0004(14) 0.0191(15) 0.0018(15) C10 0.0445(19) 0.052(2) 0.0186(14) -0.0059(14) 0.0114(14) -0.0016(16) C11 0.0300(16) 0.0416(18) 0.0265(15) -0.0032(13) 0.0066(13) -0.0014(14) C12 0.076(3) 0.120(4) 0.042(2) 0.002(2) 0.038(2) 0.015(3) C13 0.0330(16) 0.0321(16) 0.0239(14) 0.0062(12) 0.0112(13) 0.0032(14) C14 0.0231(14) 0.0289(15) 0.0222(14) 0.0005(11) 0.0094(12) 0.0010(12) C15 0.0274(15) 0.0263(15) 0.0215(13) 0.0011(11) 0.0090(12) -0.0011(12) C16 0.0260(15) 0.0292(16) 0.0269(15) 0.0015(12) 0.0080(12) 0.0011(12) C17 0.0235(14) 0.0249(15) 0.0196(13) -0.0009(11) 0.0046(11) -0.0017(12) C18 0.0316(16) 0.0228(15) 0.0232(14) 0.0001(11) 0.0102(12) 0.0001(12) C19 0.0364(17) 0.0398(18) 0.0248(15) 0.0044(13) 0.0100(13) 0.0064(14) C20 0.0340(17) 0.0392(19) 0.0439(19) 0.0035(15) 0.0172(15) 0.0130(15) C21 0.0406(18) 0.0365(18) 0.0364(17) -0.0038(14) 0.0244(15) -0.0009(15) C22 0.0404(18) 0.0438(19) 0.0216(15) -0.0043(13) 0.0079(13) -0.0035(15) C23 0.0299(16) 0.0337(17) 0.0269(15) -0.0019(12) 0.0086(13) 0.0008(13) C24 0.071(3) 0.082(3) 0.072(3) 0.000(2) 0.045(2) 0.026(3) C25 0.0355(15) 0.108(3) 0.088(2) 0.033(2) 0.0258(16) -0.0029(17) C26 0.0355(15) 0.108(3) 0.088(2) 0.033(2) 0.0258(16) -0.0029(17) C27 0.076(3) 0.089(4) 0.077(3) 0.012(3) 0.047(3) -0.026(3) C28 0.085(3) 0.078(3) 0.068(3) 0.037(2) 0.040(3) 0.009(3) C29 0.053(2) 0.068(3) 0.058(2) 0.029(2) 0.029(2) 0.016(2) _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 Co1 O3 2.048(2) . ? Co1 O1 2.0573(19) . ? Co1 O4 2.1025(19) 2_545 ? Co1 N5 2.122(2) . ? Co1 O5 2.131(2) . ? Co1 N1 2.141(2) 2_545 ? Co2 O2 2.0401(19) . ? Co2 O2 2.0401(19) 3_666 ? Co2 N4 2.116(2) 3_656 ? Co2 N4 2.116(2) 1_565 ? Co2 O8 2.149(2) 3_656 ? Co2 O8 2.149(2) 1_565 ? N1 C5 1.335(3) . ? N1 C3 1.377(3) . ? N1 Co1 2.141(2) 2 ? N2 C5 1.354(4) . ? N2 C2 1.372(3) . ? N2 H2A 0.8600 . ? N3 C17 1.358(3) . ? N3 C14 1.360(3) . ? N3 H3A 0.8600 . ? N4 C17 1.332(3) . ? N4 C15 1.372(3) . ? N4 Co2 2.116(2) 1_545 ? N5 C29 1.319(4) . ? N5 C25 1.327(5) . ? O1 C1 1.248(3) . ? O2 C1 1.260(3) . ? O3 C4 1.242(3) . ? O4 C4 1.275(3) . ? O4 Co1 2.1025(19) 2 ? O5 C13 1.228(3) . ? O6 C13 1.287(4) . ? O6 H6 0.8200 . ? O7 C16 1.260(3) . ? O8 C16 1.251(3) . ? O8 Co2 2.149(2) 1_545 ? O9 C9 1.365(4) . ? O9 C12 1.431(4) . ? O10 C21 1.373(3) . ? O10 C24 1.414(4) . ? O11 H1W 0.8499 . ? O11 H2W 0.8501 . ? O12 H3W 0.8499 . ? O12 H4W 0.8496 . ? C1 C2 1.491(4) . ? C2 C3 1.376(4) . ? C3 C4 1.490(4) . ? C5 C6 1.458(4) . ? C6 C11 1.380(4) . ? C6 C7 1.393(4) . ? C7 C8 1.366(4) . ? C7 H7A 0.9300 . ? C8 C9 1.390(4) . ? C8 H8A 0.9300 . ? C9 C10 1.377(4) . ? C10 C11 1.388(4) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.474(4) . ? C14 C15 1.370(4) . ? C15 C16 1.489(4) . ? C17 C18 1.455(4) . ? C18 C19 1.386(4) . ? C18 C23 1.408(4) . ? C19 C20 1.382(4) . ? C19 H19A 0.9300 . ? C20 C21 1.381(4) . ? C20 H20A 0.9300 . ? C21 C22 1.385(4) . ? C22 C23 1.367(4) . ? C22 H22A 0.9300 . ? C23 H23A 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.359(5) . ? C25 H25A 0.9300 . ? C26 C27 1.372(6) . ? C26 H26A 0.9300 . ? C27 C28 1.347(6) . ? C27 H27A 0.9300 . ? C28 C29 1.378(5) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? 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 O3 Co1 O1 91.60(8) . . ? O3 Co1 O4 92.35(8) . 2_545 ? O1 Co1 O4 85.22(7) . 2_545 ? O3 Co1 N5 88.74(9) . . ? O1 Co1 N5 90.89(9) . . ? O4 Co1 N5 175.98(8) 2_545 . ? O3 Co1 O5 176.49(7) . . ? O1 Co1 O5 90.81(8) . . ? O4 Co1 O5 90.40(8) 2_545 . ? N5 Co1 O5 88.66(9) . . ? O3 Co1 N1 90.27(9) . 2_545 ? O1 Co1 N1 162.19(8) . 2_545 ? O4 Co1 N1 77.01(8) 2_545 2_545 ? N5 Co1 N1 106.86(9) . 2_545 ? O5 Co1 N1 88.22(9) . 2_545 ? O2 Co2 O2 180.000 . 3_666 ? O2 Co2 N4 90.32(8) . 3_656 ? O2 Co2 N4 89.68(8) 3_666 3_656 ? O2 Co2 N4 89.68(8) . 1_565 ? O2 Co2 N4 90.32(8) 3_666 1_565 ? N4 Co2 N4 180.000 3_656 1_565 ? O2 Co2 O8 90.89(8) . 3_656 ? O2 Co2 O8 89.11(8) 3_666 3_656 ? N4 Co2 O8 78.05(8) 3_656 3_656 ? N4 Co2 O8 101.95(8) 1_565 3_656 ? O2 Co2 O8 89.11(8) . 1_565 ? O2 Co2 O8 90.89(8) 3_666 1_565 ? N4 Co2 O8 101.95(8) 3_656 1_565 ? N4 Co2 O8 78.05(8) 1_565 1_565 ? O8 Co2 O8 180.000 3_656 1_565 ? C5 N1 C3 106.4(2) . . ? C5 N1 Co1 140.62(19) . 2 ? C3 N1 Co1 111.56(16) . 2 ? C5 N2 C2 109.3(2) . . ? C5 N2 H2A 125.3 . . ? C2 N2 H2A 125.3 . . ? C17 N3 C14 108.7(2) . . ? C17 N3 H3A 125.7 . . ? C14 N3 H3A 125.7 . . ? C17 N4 C15 106.5(2) . . ? C17 N4 Co2 141.31(19) . 1_545 ? C15 N4 Co2 107.29(17) . 1_545 ? C29 N5 C25 116.5(3) . . ? C29 N5 Co1 121.7(2) . . ? C25 N5 Co1 121.8(3) . . ? C1 O1 Co1 130.15(18) . . ? C1 O2 Co2 139.17(18) . . ? C4 O3 Co1 132.48(17) . . ? C4 O4 Co1 118.56(16) . 2 ? C13 O5 Co1 150.63(19) . . ? C13 O6 H6 109.5 . . ? C16 O8 Co2 111.56(18) . 1_545 ? C9 O9 C12 118.3(3) . . ? C21 O10 C24 117.8(3) . . ? H1W O11 H2W 104.7 . . ? H3W O12 H4W 104.2 . . ? O1 C1 O2 124.1(3) . . ? O1 C1 C2 121.2(2) . . ? O2 C1 C2 114.6(2) . . ? N2 C2 C3 104.8(2) . . ? N2 C2 C1 118.9(2) . . ? C3 C2 C1 136.3(2) . . ? C2 C3 N1 110.0(2) . . ? C2 C3 C4 133.7(3) . . ? N1 C3 C4 116.2(2) . . ? O3 C4 O4 122.6(2) . . ? O3 C4 C3 122.9(2) . . ? O4 C4 C3 114.5(2) . . ? N1 C5 N2 109.5(2) . . ? N1 C5 C6 125.5(3) . . ? N2 C5 C6 124.8(2) . . ? C11 C6 C7 118.9(3) . . ? C11 C6 C5 122.4(3) . . ? C7 C6 C5 118.7(2) . . ? C8 C7 C6 120.9(3) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? C7 C8 C9 119.8(3) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? O9 C9 C10 124.3(3) . . ? O9 C9 C8 115.6(3) . . ? C10 C9 C8 120.1(3) . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? C6 C11 C10 120.6(3) . . ? C6 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? O9 C12 H12A 109.5 . . ? O9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 O6 121.6(2) . . ? O5 C13 C14 121.5(3) . . ? O6 C13 C14 117.0(2) . . ? N3 C14 C15 105.7(2) . . ? N3 C14 C13 123.0(2) . . ? C15 C14 C13 131.2(3) . . ? C14 C15 N4 109.6(2) . . ? C14 C15 C16 132.9(2) . . ? N4 C15 C16 117.5(2) . . ? O8 C16 O7 125.4(3) . . ? O8 C16 C15 116.6(2) . . ? O7 C16 C15 117.9(2) . . ? N4 C17 N3 109.6(2) . . ? N4 C17 C18 125.4(2) . . ? N3 C17 C18 124.9(2) . . ? C19 C18 C23 118.4(3) . . ? C19 C18 C17 122.6(2) . . ? C23 C18 C17 119.0(3) . . ? C20 C19 C18 121.1(3) . . ? C20 C19 H19A 119.5 . . ? C18 C19 H19A 119.5 . . ? C21 C20 C19 119.6(3) . . ? C21 C20 H20A 120.2 . . ? C19 C20 H20A 120.2 . . ? O10 C21 C20 124.7(3) . . ? O10 C21 C22 115.1(3) . . ? C20 C21 C22 120.2(3) . . ? C23 C22 C21 120.3(3) . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C22 C23 C18 120.4(3) . . ? C22 C23 H23A 119.8 . . ? C18 C23 H23A 119.8 . . ? O10 C24 H24A 109.5 . . ? O10 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O10 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N5 C25 C26 123.8(4) . . ? N5 C25 H25A 118.1 . . ? C26 C25 H25A 118.1 . . ? C25 C26 C27 118.6(4) . . ? C25 C26 H26A 120.7 . . ? C27 C26 H26A 120.7 . . ? C28 C27 C26 118.8(4) . . ? C28 C27 H27A 120.6 . . ? C26 C27 H27A 120.6 . . ? C27 C28 C29 118.8(4) . . ? C27 C28 H28A 120.6 . . ? C29 C28 H28A 120.6 . . ? N5 C29 C28 123.5(4) . . ? N5 C29 H29A 118.3 . . ? C28 C29 H29A 118.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Co1 N5 C29 -29.3(3) . . . . ? O1 Co1 N5 C29 -120.9(3) . . . . ? O4 Co1 N5 C29 -135.1(12) 2_545 . . . ? O5 Co1 N5 C29 148.3(3) . . . . ? N1 Co1 N5 C29 60.6(3) 2_545 . . . ? O3 Co1 N5 C25 149.9(3) . . . . ? O1 Co1 N5 C25 58.3(3) . . . . ? O4 Co1 N5 C25 44.1(14) 2_545 . . . ? O5 Co1 N5 C25 -32.5(3) . . . . ? N1 Co1 N5 C25 -120.2(3) 2_545 . . . ? O3 Co1 O1 C1 63.2(2) . . . . ? O4 Co1 O1 C1 -29.0(2) 2_545 . . . ? N5 Co1 O1 C1 152.0(3) . . . . ? O5 Co1 O1 C1 -119.3(2) . . . . ? N1 Co1 O1 C1 -32.6(4) 2_545 . . . ? O2 Co2 O2 C1 -67(100) 3_666 . . . ? N4 Co2 O2 C1 -178.2(3) 3_656 . . . ? N4 Co2 O2 C1 1.8(3) 1_565 . . . ? O8 Co2 O2 C1 103.8(3) 3_656 . . . ? O8 Co2 O2 C1 -76.2(3) 1_565 . . . ? O1 Co1 O3 C4 -57.8(3) . . . . ? O4 Co1 O3 C4 27.5(3) 2_545 . . . ? N5 Co1 O3 C4 -148.7(3) . . . . ? O5 Co1 O3 C4 169.0(13) . . . . ? N1 Co1 O3 C4 104.5(3) 2_545 . . . ? O3 Co1 O5 C13 160.6(13) . . . . ? O1 Co1 O5 C13 27.3(4) . . . . ? O4 Co1 O5 C13 -57.9(4) 2_545 . . . ? N5 Co1 O5 C13 118.2(4) . . . . ? N1 Co1 O5 C13 -134.9(4) 2_545 . . . ? Co1 O1 C1 O2 140.9(2) . . . . ? Co1 O1 C1 C2 -36.6(4) . . . . ? Co2 O2 C1 O1 109.5(3) . . . . ? Co2 O2 C1 C2 -72.9(3) . . . . ? C5 N2 C2 C3 1.5(3) . . . . ? C5 N2 C2 C1 -176.4(2) . . . . ? O1 C1 C2 N2 169.7(2) . . . . ? O2 C1 C2 N2 -8.0(4) . . . . ? O1 C1 C2 C3 -7.5(5) . . . . ? O2 C1 C2 C3 174.8(3) . . . . ? N2 C2 C3 N1 0.4(3) . . . . ? C1 C2 C3 N1 177.8(3) . . . . ? N2 C2 C3 C4 -175.3(3) . . . . ? C1 C2 C3 C4 2.0(6) . . . . ? C5 N1 C3 C2 -2.1(3) . . . . ? Co1 N1 C3 C2 167.04(18) 2 . . . ? C5 N1 C3 C4 174.4(2) . . . . ? Co1 N1 C3 C4 -16.4(3) 2 . . . ? Co1 O3 C4 O4 -150.3(2) . . . . ? Co1 O3 C4 C3 27.9(4) . . . . ? Co1 O4 C4 O3 176.8(2) 2 . . . ? Co1 O4 C4 C3 -1.5(3) 2 . . . ? C2 C3 C4 O3 9.6(5) . . . . ? N1 C3 C4 O3 -165.9(3) . . . . ? C2 C3 C4 O4 -172.1(3) . . . . ? N1 C3 C4 O4 12.4(3) . . . . ? C3 N1 C5 N2 3.1(3) . . . . ? Co1 N1 C5 N2 -160.9(2) 2 . . . ? C3 N1 C5 C6 -172.6(3) . . . . ? Co1 N1 C5 C6 23.4(5) 2 . . . ? C2 N2 C5 N1 -2.9(3) . . . . ? C2 N2 C5 C6 172.7(3) . . . . ? N1 C5 C6 C11 -149.1(3) . . . . ? N2 C5 C6 C11 35.9(4) . . . . ? N1 C5 C6 C7 32.3(4) . . . . ? N2 C5 C6 C7 -142.6(3) . . . . ? C11 C6 C7 C8 1.1(5) . . . . ? C5 C6 C7 C8 179.7(3) . . . . ? C6 C7 C8 C9 -0.3(5) . . . . ? C12 O9 C9 C10 -7.8(5) . . . . ? C12 O9 C9 C8 171.8(4) . . . . ? C7 C8 C9 O9 -180.0 . . . . ? C7 C8 C9 C10 -0.4(5) . . . . ? O9 C9 C10 C11 179.7(3) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C7 C6 C11 C10 -1.3(5) . . . . ? C5 C6 C11 C10 -179.9(3) . . . . ? C9 C10 C11 C6 0.7(5) . . . . ? Co1 O5 C13 O6 -147.6(3) . . . . ? Co1 O5 C13 C14 32.2(6) . . . . ? C17 N3 C14 C15 0.4(3) . . . . ? C17 N3 C14 C13 -179.4(3) . . . . ? O5 C13 C14 N3 -1.7(5) . . . . ? O6 C13 C14 N3 178.0(3) . . . . ? O5 C13 C14 C15 178.6(3) . . . . ? O6 C13 C14 C15 -1.6(5) . . . . ? N3 C14 C15 N4 0.7(3) . . . . ? C13 C14 C15 N4 -179.7(3) . . . . ? N3 C14 C15 C16 -175.8(3) . . . . ? C13 C14 C15 C16 3.8(5) . . . . ? C17 N4 C15 C14 -1.4(3) . . . . ? Co2 N4 C15 C14 159.37(19) 1_545 . . . ? C17 N4 C15 C16 175.7(2) . . . . ? Co2 N4 C15 C16 -23.5(3) 1_545 . . . ? Co2 O8 C16 O7 -161.3(3) 1_545 . . . ? Co2 O8 C16 C15 19.5(3) 1_545 . . . ? C14 C15 C16 O8 179.3(3) . . . . ? N4 C15 C16 O8 3.0(4) . . . . ? C14 C15 C16 O7 0.0(5) . . . . ? N4 C15 C16 O7 -176.3(3) . . . . ? C15 N4 C17 N3 1.6(3) . . . . ? Co2 N4 C17 N3 -148.2(2) 1_545 . . . ? C15 N4 C17 C18 -174.0(3) . . . . ? Co2 N4 C17 C18 36.1(5) 1_545 . . . ? C14 N3 C17 N4 -1.3(3) . . . . ? C14 N3 C17 C18 174.4(3) . . . . ? N4 C17 C18 C19 -164.3(3) . . . . ? N3 C17 C18 C19 20.7(4) . . . . ? N4 C17 C18 C23 17.2(4) . . . . ? N3 C17 C18 C23 -157.8(3) . . . . ? C23 C18 C19 C20 -0.8(5) . . . . ? C17 C18 C19 C20 -179.3(3) . . . . ? C18 C19 C20 C21 -1.2(5) . . . . ? C24 O10 C21 C20 7.4(5) . . . . ? C24 O10 C21 C22 -172.3(3) . . . . ? C19 C20 C21 O10 -177.5(3) . . . . ? C19 C20 C21 C22 2.3(5) . . . . ? O10 C21 C22 C23 178.5(3) . . . . ? C20 C21 C22 C23 -1.3(5) . . . . ? C21 C22 C23 C18 -0.7(5) . . . . ? C19 C18 C23 C22 1.8(4) . . . . ? C17 C18 C23 C22 -179.7(3) . . . . ? C29 N5 C25 C26 -1.9(7) . . . . ? Co1 N5 C25 C26 178.9(4) . . . . ? N5 C25 C26 C27 0.2(8) . . . . ? C25 C26 C27 C28 1.5(8) . . . . ? C26 C27 C28 C29 -1.4(8) . . . . ? C25 N5 C29 C28 2.0(6) . . . . ? Co1 N5 C29 C28 -178.8(4) . . . . ? C27 C28 C29 N5 -0.4(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O7 0.82 1.65 2.466(3) 172.6 . N3 H3A O4 0.86 1.95 2.779(3) 162.1 2_545 O11 H2W O10 0.85 2.16 2.942(4) 152.5 1_565 O12 H3W O7 0.85 2.12 2.904(4) 154.1 1_565 N2 H2A O8 0.86 2.20 3.025(3) 161.0 3_656 O12 H4W O11 0.85 1.89 2.735(5) 179.6 3_666 O11 H1W O12 0.85 1.90 2.742(5) 169.0 4_576 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.651 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.078