# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_100407b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26.50 Cl Co0.50 N4 O4.25' _chemical_formula_weight 503.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c 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' '-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 15.3403(10) _cell_length_b 21.9052(10) _cell_length_c 16.9452(14) _cell_angle_alpha 90.00 _cell_angle_beta 113.4260(10) _cell_angle_gamma 90.00 _cell_volume 5224.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6324 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description BLOCK _exptl_crystal_colour PINK _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 0.484 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9011 _exptl_absorpt_correction_T_max 0.9180 _exptl_absorpt_process_details SADABS _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 13100 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4609 _reflns_number_gt 3691 _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. The unit cell contains 8 water molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. ; _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^)+(0.1788P)^2^+1.7535P] 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 4609 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.2463 _refine_ls_wR_factor_gt 0.2349 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 0.5000 0.33402(3) 0.7500 0.0393(3) Uani 1 2 d S . . Cl1 Cl 0.5000 0.13710(8) 0.7500 0.0746(5) Uani 1 2 d S . . Cl2 Cl 0.2564(4) 0.2808(2) 0.8267(4) 0.1148(16) Uani 0.370(3) 1 d P A 1 Cl2' Cl 0.1218(11) 0.3606(6) 0.7203(10) 0.1148(16) Uani 0.130(3) 1 d P A 2 N1 N 0.4501(2) 0.40329(13) 0.81125(19) 0.0452(7) Uani 1 1 d . . . N2 N 0.3533(2) 0.46215(15) 0.8489(2) 0.0523(8) Uani 1 1 d . . . N3 N 0.2261(2) 0.33539(13) 0.5344(2) 0.0485(8) Uani 1 1 d . . . N4 N 0.3758(2) 0.32658(13) 0.6301(2) 0.0454(7) Uani 1 1 d . . . O1 O 0.1946(2) 0.50457(14) 0.70180(19) 0.0649(8) Uani 1 1 d . . . O2 O 0.1424(2) 0.44905(12) 0.55671(18) 0.0573(7) Uani 1 1 d . . . O3 O 0.4350(2) 0.26045(14) 0.7934(2) 0.0640(8) Uani 1 1 d . . . H3A H 0.4454 0.2241 0.7817 0.096 Uiso 1 1 d R . . H3B H 0.3817 0.2675 0.7959 0.096 Uiso 1 1 d R . . O4 O 0.5000 0.9827(8) 0.7500 0.133(5) Uani 0.50 2 d SP . . C1 C 0.4982(3) 0.45677(16) 0.8501(2) 0.0463(8) Uani 1 1 d . . . C2 C 0.4376(3) 0.49341(18) 0.8734(2) 0.0492(9) Uani 1 1 d . . . C3 C 0.4655(3) 0.5494(2) 0.9152(3) 0.0632(11) Uani 1 1 d . . . H3 H 0.4244 0.5727 0.9312 0.076 Uiso 1 1 calc R . . C4 C 0.5554(3) 0.5684(2) 0.9314(3) 0.0667(12) Uani 1 1 d . . . H4 H 0.5758 0.6059 0.9583 0.080 Uiso 1 1 calc R . . C5 C 0.6187(3) 0.5327(2) 0.9085(3) 0.0659(11) Uani 1 1 d . . . H5 H 0.6796 0.5471 0.9202 0.079 Uiso 1 1 calc R . . C6 C 0.5909(3) 0.47655(18) 0.8688(3) 0.0543(9) Uani 1 1 d . . . H6 H 0.6329 0.4526 0.8549 0.065 Uiso 1 1 calc R . . C7 C 0.3656(3) 0.40892(17) 0.8122(2) 0.0499(9) Uani 1 1 d . . . H7 H 0.3183 0.3795 0.7900 0.060 Uiso 1 1 calc R . . C8 C 0.2657(3) 0.4848(2) 0.8500(3) 0.0681(13) Uani 1 1 d . . . H8A H 0.2774 0.5012 0.9064 0.082 Uiso 1 1 calc R . . H8B H 0.2208 0.4514 0.8389 0.082 Uiso 1 1 calc R . . C9 C 0.2240(3) 0.5335(2) 0.7836(3) 0.0691(12) Uani 1 1 d . . . H9A H 0.1701 0.5524 0.7902 0.083 Uiso 1 1 calc R . . H9B H 0.2710 0.5647 0.7895 0.083 Uiso 1 1 calc R . . C10 C 0.1634(3) 0.54173(19) 0.6308(3) 0.0559(10) Uani 1 1 d . . . C11 C 0.1346(3) 0.51113(18) 0.5507(3) 0.0531(10) Uani 1 1 d . . . C12 C 0.1040(3) 0.5443(2) 0.4766(3) 0.0628(11) Uani 1 1 d . . . H12 H 0.0851 0.5242 0.4241 0.075 Uiso 1 1 calc R . . C13 C 0.1009(4) 0.6072(2) 0.4785(4) 0.0805(15) Uani 1 1 d . . . H13 H 0.0796 0.6294 0.4275 0.097 Uiso 1 1 calc R . . C14 C 0.1298(4) 0.6370(2) 0.5573(4) 0.0871(16) Uani 1 1 d . . . H14 H 0.1285 0.6794 0.5592 0.105 Uiso 1 1 calc R . . C15 C 0.1601(3) 0.6042(2) 0.6316(4) 0.0758(14) Uani 1 1 d . . . H15 H 0.1789 0.6245 0.6839 0.091 Uiso 1 1 calc R . . C16 C 0.1072(3) 0.41608(18) 0.4780(3) 0.0552(10) Uani 1 1 d . . . H16A H 0.1402 0.4283 0.4422 0.066 Uiso 1 1 calc R . . H16B H 0.0399 0.4238 0.4469 0.066 Uiso 1 1 calc R . . C17 C 0.1244(3) 0.34969(18) 0.5010(3) 0.0547(10) Uani 1 1 d . . . H17A H 0.0998 0.3397 0.5441 0.066 Uiso 1 1 calc R . . H17B H 0.0907 0.3250 0.4505 0.066 Uiso 1 1 calc R . . C18 C 0.2798(3) 0.32507(16) 0.4871(2) 0.0466(9) Uani 1 1 d . . . C19 C 0.3738(3) 0.31909(16) 0.5471(2) 0.0450(8) Uani 1 1 d . . . C20 C 0.4442(3) 0.30615(18) 0.5191(3) 0.0524(9) Uani 1 1 d . . . H20 H 0.5072 0.3029 0.5578 0.063 Uiso 1 1 calc R . . C21 C 0.4190(3) 0.2980(2) 0.4320(3) 0.0619(11) Uani 1 1 d . . . H21 H 0.4656 0.2879 0.4122 0.074 Uiso 1 1 calc R . . C22 C 0.3250(3) 0.3047(2) 0.3731(3) 0.0672(12) Uani 1 1 d . . . H22 H 0.3107 0.2996 0.3147 0.081 Uiso 1 1 calc R . . C23 C 0.2537(3) 0.31843(19) 0.3992(3) 0.0576(10) Uani 1 1 d . . . H23 H 0.1911 0.3231 0.3602 0.069 Uiso 1 1 calc R . . C24 C 0.2868(3) 0.33555(16) 0.6178(2) 0.0474(9) Uani 1 1 d . . . H24 H 0.2672 0.3415 0.6627 0.057 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 0.0385(4) 0.0361(4) 0.0400(4) 0.000 0.0120(3) 0.000 Cl1 0.0641(9) 0.0716(11) 0.0815(12) 0.000 0.0219(8) 0.000 Cl2 0.145(4) 0.090(3) 0.138(4) -0.023(2) 0.086(4) -0.037(3) Cl2' 0.145(4) 0.090(3) 0.138(4) -0.023(2) 0.086(4) -0.037(3) N1 0.0446(16) 0.0429(16) 0.0463(17) -0.0006(13) 0.0163(13) 0.0037(13) N2 0.0484(17) 0.062(2) 0.0464(18) -0.0060(14) 0.0183(14) 0.0056(14) N3 0.0428(16) 0.0432(17) 0.0501(19) -0.0036(13) 0.0084(14) -0.0037(12) N4 0.0451(17) 0.0404(16) 0.0444(17) 0.0003(12) 0.0110(14) -0.0026(12) O1 0.0644(18) 0.0592(17) 0.0582(18) -0.0150(13) 0.0107(14) 0.0078(14) O2 0.0608(16) 0.0484(15) 0.0517(16) -0.0034(12) 0.0106(13) 0.0053(12) O3 0.0698(19) 0.0581(17) 0.0622(18) 0.0021(13) 0.0243(15) -0.0089(14) O4 0.119(11) 0.157(14) 0.124(12) 0.000 0.049(9) 0.000 C1 0.049(2) 0.0419(19) 0.043(2) -0.0018(14) 0.0139(16) 0.0055(15) C2 0.048(2) 0.051(2) 0.0419(19) -0.0057(15) 0.0104(16) 0.0077(16) C3 0.067(3) 0.058(2) 0.059(3) -0.0120(19) 0.019(2) 0.015(2) C4 0.064(3) 0.055(2) 0.067(3) -0.019(2) 0.011(2) 0.003(2) C5 0.058(2) 0.057(2) 0.072(3) -0.014(2) 0.015(2) -0.007(2) C6 0.046(2) 0.050(2) 0.061(2) -0.0075(18) 0.0152(18) 0.0050(16) C7 0.052(2) 0.049(2) 0.046(2) 0.0005(16) 0.0176(17) -0.0017(17) C8 0.051(2) 0.100(4) 0.055(3) -0.019(2) 0.023(2) 0.013(2) C9 0.058(2) 0.078(3) 0.064(3) -0.019(2) 0.016(2) 0.020(2) C10 0.0405(19) 0.057(2) 0.064(3) -0.0061(18) 0.0144(18) 0.0043(16) C11 0.0392(19) 0.048(2) 0.068(3) -0.0037(18) 0.0172(18) 0.0024(15) C12 0.057(2) 0.064(3) 0.064(3) 0.009(2) 0.021(2) 0.007(2) C13 0.074(3) 0.066(3) 0.096(4) 0.020(3) 0.028(3) -0.001(2) C14 0.086(3) 0.052(3) 0.109(5) 0.006(3) 0.023(3) -0.002(2) C15 0.061(3) 0.059(3) 0.094(4) -0.017(3) 0.018(3) 0.003(2) C16 0.047(2) 0.055(2) 0.051(2) -0.0008(17) 0.0073(17) 0.0043(17) C17 0.0402(19) 0.053(2) 0.058(2) -0.0045(18) 0.0054(18) -0.0029(16) C18 0.051(2) 0.0344(17) 0.047(2) -0.0021(14) 0.0111(17) -0.0071(15) C19 0.052(2) 0.0329(16) 0.044(2) 0.0019(14) 0.0121(16) -0.0050(15) C20 0.053(2) 0.047(2) 0.057(2) -0.0003(17) 0.0212(19) -0.0027(17) C21 0.074(3) 0.060(3) 0.059(3) -0.0010(19) 0.035(2) -0.006(2) C22 0.086(3) 0.065(3) 0.046(2) -0.0028(19) 0.021(2) -0.013(2) C23 0.065(3) 0.049(2) 0.047(2) 0.0003(17) 0.010(2) -0.0080(19) C24 0.045(2) 0.047(2) 0.045(2) -0.0022(15) 0.0123(17) -0.0052(15) _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 2.144(3) . ? Co1 N1 2.144(3) 2_656 ? Co1 N4 2.169(3) . ? Co1 N4 2.169(3) 2_656 ? Co1 O3 2.171(3) 2_656 ? Co1 O3 2.171(3) . ? N1 C7 1.309(5) . ? N1 C1 1.402(5) . ? N2 C7 1.369(5) . ? N2 C2 1.374(5) . ? N2 C8 1.440(5) . ? N3 C24 1.349(5) . ? N3 C18 1.377(5) . ? N3 C17 1.467(5) . ? N4 C24 1.311(5) . ? N4 C19 1.404(5) . ? O1 C10 1.372(5) . ? O1 C9 1.424(5) . ? O2 C11 1.365(5) . ? O2 C16 1.421(5) . ? O3 H3A 0.8501 . ? O3 H3B 0.8504 . ? C1 C6 1.396(6) . ? C1 C2 1.398(5) . ? C2 C3 1.396(6) . ? C3 C4 1.360(6) . ? C3 H3 0.9300 . ? C4 C5 1.417(6) . ? C4 H4 0.9300 . ? C5 C6 1.385(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.497(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.368(6) . ? C10 C11 1.417(6) . ? C11 C12 1.362(6) . ? C12 C13 1.380(7) . ? C12 H12 0.9300 . ? C13 C14 1.391(9) . ? C13 H13 0.9300 . ? C14 C15 1.361(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.501(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.387(6) . ? C18 C19 1.402(5) . ? C19 C20 1.371(5) . ? C20 C21 1.381(6) . ? C20 H20 0.9300 . ? C21 C22 1.397(7) . ? C21 H21 0.9300 . ? C22 C23 1.367(6) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 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 N1 Co1 N1 89.91(17) . 2_656 ? N1 Co1 N4 99.01(12) . . ? N1 Co1 N4 87.12(11) 2_656 . ? N1 Co1 N4 87.12(11) . 2_656 ? N1 Co1 N4 99.01(12) 2_656 2_656 ? N4 Co1 N4 171.38(15) . 2_656 ? N1 Co1 O3 171.70(11) . 2_656 ? N1 Co1 O3 93.51(12) 2_656 2_656 ? N4 Co1 O3 88.73(12) . 2_656 ? N4 Co1 O3 84.87(12) 2_656 2_656 ? N1 Co1 O3 93.51(13) . . ? N1 Co1 O3 171.70(11) 2_656 . ? N4 Co1 O3 84.87(12) . . ? N4 Co1 O3 88.73(12) 2_656 . ? O3 Co1 O3 84.14(18) 2_656 . ? C7 N1 C1 104.8(3) . . ? C7 N1 Co1 128.2(3) . . ? C1 N1 Co1 126.6(2) . . ? C7 N2 C2 106.2(3) . . ? C7 N2 C8 126.6(4) . . ? C2 N2 C8 126.6(4) . . ? C24 N3 C18 106.7(3) . . ? C24 N3 C17 126.1(4) . . ? C18 N3 C17 127.0(3) . . ? C24 N4 C19 104.6(3) . . ? C24 N4 Co1 127.5(3) . . ? C19 N4 Co1 127.4(2) . . ? C10 O1 C9 117.1(3) . . ? C11 O2 C16 116.6(3) . . ? Co1 O3 H3A 117.6 . . ? Co1 O3 H3B 117.5 . . ? H3A O3 H3B 117.1 . . ? C6 C1 C2 119.2(3) . . ? C6 C1 N1 131.6(3) . . ? C2 C1 N1 109.1(3) . . ? N2 C2 C3 130.7(4) . . ? N2 C2 C1 106.3(3) . . ? C3 C2 C1 123.0(4) . . ? C4 C3 C2 116.9(4) . . ? C4 C3 H3 121.6 . . ? C2 C3 H3 121.6 . . ? C3 C4 C5 121.7(4) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 120.8(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.4(4) . . ? C5 C6 H6 120.8 . . ? C1 C6 H6 120.8 . . ? N1 C7 N2 113.7(3) . . ? N1 C7 H7 123.2 . . ? N2 C7 H7 123.2 . . ? N2 C8 C9 111.0(4) . . ? N2 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N2 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O1 C9 C8 106.9(4) . . ? O1 C9 H9A 110.3 . . ? C8 C9 H9A 110.3 . . ? O1 C9 H9B 110.3 . . ? C8 C9 H9B 110.3 . . ? H9A C9 H9B 108.6 . . ? C15 C10 O1 125.8(4) . . ? C15 C10 C11 118.9(4) . . ? O1 C10 C11 115.2(4) . . ? C12 C11 O2 126.0(4) . . ? C12 C11 C10 119.5(4) . . ? O2 C11 C10 114.5(4) . . ? C11 C12 C13 120.9(5) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 119.3(5) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 120.1(5) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 121.3(5) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? O2 C16 C17 106.7(3) . . ? O2 C16 H16A 110.4 . . ? C17 C16 H16A 110.4 . . ? O2 C16 H16B 110.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? N3 C17 C16 110.9(3) . . ? N3 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.0 . . ? N3 C18 C23 131.2(4) . . ? N3 C18 C19 105.9(3) . . ? C23 C18 C19 122.9(4) . . ? C20 C19 C18 119.5(4) . . ? C20 C19 N4 131.6(3) . . ? C18 C19 N4 108.8(3) . . ? C19 C20 C21 118.2(4) . . ? C19 C20 H20 120.9 . . ? C21 C20 H20 120.9 . . ? C20 C21 C22 121.5(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 121.5(4) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C18 116.4(4) . . ? C22 C23 H23 121.8 . . ? C18 C23 H23 121.8 . . ? N4 C24 N3 114.0(4) . . ? N4 C24 H24 123.0 . . ? N3 C24 H24 123.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Co1 N1 C7 128.3(4) 2_656 . . . ? N4 Co1 N1 C7 41.2(3) . . . . ? N4 Co1 N1 C7 -132.7(3) 2_656 . . . ? O3 Co1 N1 C7 -117.4(8) 2_656 . . . ? O3 Co1 N1 C7 -44.2(3) . . . . ? N1 Co1 N1 C1 -43.2(2) 2_656 . . . ? N4 Co1 N1 C1 -130.2(3) . . . . ? N4 Co1 N1 C1 55.9(3) 2_656 . . . ? O3 Co1 N1 C1 71.2(9) 2_656 . . . ? O3 Co1 N1 C1 144.4(3) . . . . ? N1 Co1 N4 C24 -30.6(3) . . . . ? N1 Co1 N4 C24 -120.1(3) 2_656 . . . ? N4 Co1 N4 C24 104.3(3) 2_656 . . . ? O3 Co1 N4 C24 146.3(3) 2_656 . . . ? O3 Co1 N4 C24 62.1(3) . . . . ? N1 Co1 N4 C19 140.2(3) . . . . ? N1 Co1 N4 C19 50.7(3) 2_656 . . . ? N4 Co1 N4 C19 -84.9(3) 2_656 . . . ? O3 Co1 N4 C19 -42.8(3) 2_656 . . . ? O3 Co1 N4 C19 -127.1(3) . . . . ? C7 N1 C1 C6 178.7(4) . . . . ? Co1 N1 C1 C6 -8.2(6) . . . . ? C7 N1 C1 C2 -0.1(4) . . . . ? Co1 N1 C1 C2 173.0(2) . . . . ? C7 N2 C2 C3 -178.6(4) . . . . ? C8 N2 C2 C3 9.7(7) . . . . ? C7 N2 C2 C1 -0.2(4) . . . . ? C8 N2 C2 C1 -171.9(4) . . . . ? C6 C1 C2 N2 -178.8(4) . . . . ? N1 C1 C2 N2 0.2(4) . . . . ? C6 C1 C2 C3 -0.2(6) . . . . ? N1 C1 C2 C3 178.7(4) . . . . ? N2 C2 C3 C4 179.6(4) . . . . ? C1 C2 C3 C4 1.4(7) . . . . ? C2 C3 C4 C5 -1.1(7) . . . . ? C3 C4 C5 C6 -0.3(8) . . . . ? C4 C5 C6 C1 1.5(7) . . . . ? C2 C1 C6 C5 -1.2(6) . . . . ? N1 C1 C6 C5 -179.9(4) . . . . ? C1 N1 C7 N2 -0.1(4) . . . . ? Co1 N1 C7 N2 -173.0(2) . . . . ? C2 N2 C7 N1 0.2(4) . . . . ? C8 N2 C7 N1 171.8(4) . . . . ? C7 N2 C8 C9 -101.3(5) . . . . ? C2 N2 C8 C9 68.7(5) . . . . ? C10 O1 C9 C8 -173.1(4) . . . . ? N2 C8 C9 O1 68.1(5) . . . . ? C9 O1 C10 C15 1.7(6) . . . . ? C9 O1 C10 C11 -179.8(3) . . . . ? C16 O2 C11 C12 -6.2(6) . . . . ? C16 O2 C11 C10 175.0(3) . . . . ? C15 C10 C11 C12 -0.3(6) . . . . ? O1 C10 C11 C12 -178.9(3) . . . . ? C15 C10 C11 O2 178.6(4) . . . . ? O1 C10 C11 O2 0.0(5) . . . . ? O2 C11 C12 C13 -178.7(4) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 0.3(7) . . . . ? C12 C13 C14 C15 -0.6(8) . . . . ? C13 C14 C15 C10 0.4(9) . . . . ? O1 C10 C15 C14 178.5(5) . . . . ? C11 C10 C15 C14 0.0(7) . . . . ? C11 O2 C16 C17 179.5(3) . . . . ? C24 N3 C17 C16 92.8(4) . . . . ? C18 N3 C17 C16 -80.5(5) . . . . ? O2 C16 C17 N3 -70.1(4) . . . . ? C24 N3 C18 C23 177.5(4) . . . . ? C17 N3 C18 C23 -8.1(6) . . . . ? C24 N3 C18 C19 0.2(4) . . . . ? C17 N3 C18 C19 174.6(3) . . . . ? N3 C18 C19 C20 177.6(3) . . . . ? C23 C18 C19 C20 0.0(5) . . . . ? N3 C18 C19 N4 -0.7(4) . . . . ? C23 C18 C19 N4 -178.2(3) . . . . ? C24 N4 C19 C20 -177.2(4) . . . . ? Co1 N4 C19 C20 10.3(5) . . . . ? C24 N4 C19 C18 0.8(4) . . . . ? Co1 N4 C19 C18 -171.7(2) . . . . ? C18 C19 C20 C21 -1.5(5) . . . . ? N4 C19 C20 C21 176.3(4) . . . . ? C19 C20 C21 C22 2.1(6) . . . . ? C20 C21 C22 C23 -1.2(7) . . . . ? C21 C22 C23 C18 -0.3(6) . . . . ? N3 C18 C23 C22 -176.0(4) . . . . ? C19 C18 C23 C22 0.9(6) . . . . ? C19 N4 C24 N3 -0.7(4) . . . . ? Co1 N4 C24 N3 171.8(2) . . . . ? C18 N3 C24 N4 0.3(4) . . . . ? C17 N3 C24 N4 -174.1(3) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 -0.051 0.750 0.199 286.2 40.8 2 -0.051 0.250 0.699 286.2 40.8 _platon_squeeze_details ; The unit cell contains 8 water molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. ; _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.616 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 941767' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_91219b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Cl2 Cu N4 O2' _chemical_formula_weight 532.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 18.5630(9) _cell_length_b 12.6014(6) _cell_length_c 19.9775(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4673.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9935 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.90 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2184 _exptl_absorpt_coefficient_mu 1.193 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7793 _exptl_absorpt_correction_T_max 0.7963 _exptl_absorpt_process_details SADABS _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 21911 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4115 _reflns_number_gt 3416 _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^)+(0.0346P)^2^+5.8358P] 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 4115 _refine_ls_number_parameters 305 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.003 _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 1.047287(18) 0.40414(3) 0.040883(16) 0.03522(11) Uani 1 1 d . . . Cl1 Cl 0.94478(4) 0.54297(6) 0.07028(3) 0.04371(18) Uani 1 1 d . . . Cl2 Cl 1.15093(4) 0.48950(7) 0.06738(4) 0.0513(2) Uani 1 1 d . . . N1 N 1.04019(12) 0.33838(19) 0.13228(11) 0.0397(5) Uani 1 1 d . . . N2 N 0.99665(13) 0.2804(2) 0.22890(11) 0.0433(6) Uani 1 1 d . . . N3 N 0.97876(13) 0.29190(19) 0.01017(11) 0.0403(6) Uani 1 1 d . A . N4 N 0.87591(15) 0.2081(3) -0.00700(14) 0.0803(12) Uani 1 1 d D . . O1 O 0.86711(11) 0.15708(16) 0.21982(10) 0.0458(5) Uani 1 1 d . A . O2 O 0.79725(12) 0.1521(2) 0.10759(11) 0.0653(7) Uani 1 1 d D . . C1 C 1.08537(15) 0.2593(2) 0.15608(14) 0.0396(6) Uani 1 1 d . . . C2 C 1.05873(16) 0.2227(2) 0.21723(14) 0.0424(7) Uani 1 1 d . . . C3 C 1.09358(19) 0.1442(3) 0.25367(17) 0.0558(9) Uani 1 1 d . . . H3 H 1.0765 0.1215 0.2950 0.067 Uiso 1 1 calc R . . C4 C 1.1546(2) 0.1019(3) 0.22547(19) 0.0627(10) Uani 1 1 d . . . H4 H 1.1790 0.0483 0.2482 0.075 Uiso 1 1 calc R . . C5 C 1.18132(18) 0.1362(3) 0.16405(19) 0.0603(9) Uani 1 1 d . . . H5 H 1.2227 0.1051 0.1467 0.072 Uiso 1 1 calc R . . C6 C 1.14742(16) 0.2155(3) 0.12855(17) 0.0507(8) Uani 1 1 d . . . H6 H 1.1654 0.2390 0.0877 0.061 Uiso 1 1 calc R . . C7 C 0.98834(16) 0.3470(2) 0.17684(14) 0.0420(7) Uani 1 1 d . . . H7 H 0.9500 0.3941 0.1728 0.050 Uiso 1 1 calc R . . C8 C 0.94527(18) 0.2649(3) 0.28366(15) 0.0543(9) Uani 1 1 d . . . H8A H 0.9095 0.3209 0.2822 0.065 Uiso 1 1 calc R . . H8B H 0.9706 0.2704 0.3260 0.065 Uiso 1 1 calc R . . C9 C 0.90793(17) 0.1594(3) 0.28021(14) 0.0501(8) Uani 1 1 d . . . H9A H 0.9431 0.1024 0.2804 0.060 Uiso 1 1 calc R . . H9B H 0.8764 0.1504 0.3185 0.060 Uiso 1 1 calc R . . C10 C 0.82821(15) 0.0663(2) 0.20744(14) 0.0403(6) Uani 1 1 d . . . C11 C 0.78966(16) 0.0649(3) 0.14722(15) 0.0483(8) Uani 1 1 d . A . C12 C 0.7476(2) -0.0228(3) 0.13209(19) 0.0679(10) Uani 1 1 d . . . H12 H 0.7210 -0.0240 0.0926 0.081 Uiso 1 1 calc R A . C13 C 0.7448(2) -0.1079(3) 0.1748(2) 0.0788(12) Uani 1 1 d . A . H13 H 0.7165 -0.1664 0.1641 0.095 Uiso 1 1 calc R . . C14 C 0.7832(2) -0.1073(3) 0.2326(2) 0.0698(11) Uani 1 1 d . . . H14 H 0.7814 -0.1657 0.2611 0.084 Uiso 1 1 calc R A . C15 C 0.82509(18) -0.0199(3) 0.24957(18) 0.0535(8) Uani 1 1 d . A . H15 H 0.8510 -0.0197 0.2894 0.064 Uiso 1 1 calc R . . C16 C 0.7702(3) 0.1219(5) 0.0405(2) 0.0508(17) Uani 0.618(8) 1 d PD A 1 H16A H 0.7181 0.1168 0.0405 0.061 Uiso 0.618(8) 1 calc PR A 1 H16B H 0.7902 0.0542 0.0266 0.061 Uiso 0.618(8) 1 calc PR A 1 C17 C 0.79508(15) 0.2093(4) -0.0049(3) 0.0520(17) Uani 0.618(8) 1 d PD A 1 H17A H 0.7782 0.2772 0.0117 0.062 Uiso 0.618(8) 1 calc PR A 1 H17B H 0.7758 0.1989 -0.0495 0.062 Uiso 0.618(8) 1 calc PR A 1 C16' C 0.7664(4) 0.1862(8) 0.0451(3) 0.046(3) Uani 0.382(8) 1 d PD A 2 H16C H 0.7685 0.2627 0.0406 0.055 Uiso 0.382(8) 1 calc PR A 2 H16D H 0.7168 0.1631 0.0410 0.055 Uiso 0.382(8) 1 calc PR A 2 C17' C 0.8134(3) 0.1326(6) -0.0059(4) 0.052(3) Uani 0.382(8) 1 d PD A 2 H17C H 0.7900 0.1281 -0.0492 0.062 Uiso 0.382(8) 1 calc PR A 2 H17D H 0.8279 0.0623 0.0085 0.062 Uiso 0.382(8) 1 calc PR A 2 C18 C 0.90953(18) 0.2899(3) 0.02109(16) 0.0597(9) Uani 1 1 d . A . H18 H 0.8858 0.3411 0.0463 0.072 Uiso 1 1 calc R . . C19 C 0.99267(12) 0.20480(14) -0.02858(10) 0.0441(7) Uani 1 1 d G . . C20 C 0.92881(12) 0.1494(2) -0.03854(12) 0.0680(11) Uani 1 1 d G A . C21 C 0.92878(19) 0.0568(2) -0.07631(14) 0.117(2) Uani 1 1 d G A . H21 H 0.8861 0.0197 -0.0830 0.140 Uiso 1 1 calc R . . C22 C 0.9926(2) 0.01952(17) -0.10411(14) 0.140(3) Uani 1 1 d G A . H22 H 0.9926 -0.0425 -0.1294 0.168 Uiso 1 1 calc R . . C23 C 1.05645(19) 0.0749(2) -0.09414(14) 0.113(2) Uani 1 1 d G A . H23 H 1.0991 0.0500 -0.1127 0.136 Uiso 1 1 calc R . . C24 C 1.05649(11) 0.1676(2) -0.05638(13) 0.0684(11) Uani 1 1 d G A . H24 H 1.0992 0.2046 -0.0497 0.082 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 0.0389(2) 0.03664(19) 0.03016(19) 0.00198(14) 0.00058(14) -0.00088(14) Cl1 0.0537(4) 0.0457(4) 0.0317(3) 0.0015(3) 0.0074(3) 0.0068(3) Cl2 0.0452(4) 0.0613(5) 0.0472(4) 0.0004(4) -0.0021(3) -0.0111(4) N1 0.0408(13) 0.0445(14) 0.0336(12) 0.0065(11) -0.0023(10) -0.0024(11) N2 0.0450(14) 0.0522(15) 0.0328(13) 0.0037(11) -0.0018(11) -0.0095(12) N3 0.0398(13) 0.0462(14) 0.0349(13) -0.0006(11) 0.0008(10) -0.0027(11) N4 0.063(2) 0.143(3) 0.0354(15) -0.0046(19) 0.0026(14) -0.052(2) O1 0.0498(12) 0.0501(12) 0.0375(11) 0.0064(9) -0.0076(9) -0.0087(10) O2 0.0470(13) 0.108(2) 0.0410(12) 0.0181(13) -0.0091(10) -0.0151(13) C1 0.0395(15) 0.0420(15) 0.0373(15) 0.0051(13) -0.0071(12) -0.0092(13) C2 0.0426(16) 0.0466(17) 0.0381(16) 0.0058(13) -0.0087(13) -0.0101(13) C3 0.060(2) 0.059(2) 0.0486(18) 0.0186(17) -0.0186(16) -0.0114(17) C4 0.057(2) 0.056(2) 0.075(3) 0.0168(19) -0.0262(19) -0.0030(17) C5 0.0458(19) 0.056(2) 0.079(3) -0.0003(19) -0.0132(18) 0.0023(16) C6 0.0424(17) 0.058(2) 0.0522(19) 0.0034(16) -0.0024(14) -0.0050(15) C7 0.0444(16) 0.0451(17) 0.0365(15) 0.0039(13) -0.0044(13) -0.0027(13) C8 0.061(2) 0.072(2) 0.0295(15) -0.0029(15) 0.0036(14) -0.0200(17) C9 0.0519(18) 0.067(2) 0.0312(15) 0.0067(14) -0.0017(13) -0.0157(16) C10 0.0338(14) 0.0457(16) 0.0414(16) -0.0037(13) 0.0035(12) -0.0002(13) C11 0.0383(16) 0.067(2) 0.0397(16) -0.0069(16) 0.0038(13) -0.0028(15) C12 0.052(2) 0.088(3) 0.064(2) -0.027(2) 0.0005(18) -0.013(2) C13 0.068(3) 0.062(2) 0.106(4) -0.026(3) 0.004(3) -0.014(2) C14 0.066(2) 0.0430(19) 0.101(3) 0.003(2) 0.007(2) -0.0019(17) C15 0.0497(18) 0.0504(18) 0.060(2) 0.0084(16) -0.0006(15) 0.0035(15) C16 0.039(3) 0.073(4) 0.040(3) 0.005(3) -0.008(2) -0.017(3) C17 0.044(3) 0.070(4) 0.042(3) 0.004(3) -0.013(2) -0.008(3) C16' 0.034(4) 0.047(6) 0.057(6) 0.000(5) -0.008(4) -0.002(5) C17' 0.055(5) 0.054(6) 0.046(5) -0.006(4) -0.003(4) -0.014(5) C18 0.0465(19) 0.094(3) 0.0380(17) -0.0032(18) 0.0045(14) -0.0073(19) C19 0.063(2) 0.0360(16) 0.0330(15) 0.0023(12) -0.0076(14) 0.0004(14) C20 0.103(3) 0.066(2) 0.0344(17) 0.0115(17) -0.0140(19) -0.042(2) C21 0.236(7) 0.069(3) 0.046(2) 0.001(2) -0.026(3) -0.083(4) C22 0.303(10) 0.049(3) 0.068(3) -0.022(2) -0.045(5) 0.013(4) C23 0.178(6) 0.088(3) 0.075(3) -0.032(3) -0.026(3) 0.078(4) C24 0.077(3) 0.067(2) 0.061(2) -0.0124(19) -0.0119(19) 0.028(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 N3 1.999(2) . ? Cu1 N1 2.009(2) . ? Cu1 Cl2 2.2669(8) . ? Cu1 Cl1 2.3233(8) 5_765 ? Cu1 Cl1 2.6507(8) . ? Cl1 Cu1 2.3232(8) 5_765 ? N1 C7 1.316(4) . ? N1 C1 1.387(4) . ? N2 C7 1.345(4) . ? N2 C2 1.382(4) . ? N2 C8 1.464(4) . ? N3 C18 1.304(4) . ? N3 C19 1.368(3) . ? N4 C18 1.329(5) . ? N4 C20 1.382(4) . ? N4 C17' 1.5002(10) . ? N4 C17 1.5012(10) . ? O1 C10 1.375(3) . ? O1 C9 1.425(3) . ? O2 C11 1.362(4) . ? O2 C16' 1.439(7) . ? O2 C16 1.481(5) . ? C1 C6 1.390(4) . ? C1 C2 1.396(4) . ? C2 C3 1.388(4) . ? C3 C4 1.374(5) . ? C3 H3 0.9300 . ? C4 C5 1.392(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.501(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.376(4) . ? C10 C11 1.400(4) . ? C11 C12 1.387(5) . ? C12 C13 1.371(6) . ? C12 H12 0.9300 . ? C13 C14 1.357(6) . ? C13 H13 0.9300 . ? C14 C15 1.391(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.4998(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C16' C17' 1.5000(10) . ? C16' H16C 0.9700 . ? C16' H16D 0.9700 . ? C17' H17C 0.9700 . ? C17' H17D 0.9700 . ? C18 H18 0.9300 . ? C19 C20 1.3900 . ? C19 C24 1.3900 . ? C20 C21 1.3900 . ? C21 C22 1.3900 . ? C21 H21 0.9300 . ? C22 C23 1.3900 . ? C22 H22 0.9300 . ? C23 C24 1.3900 . ? C23 H23 0.9300 . ? C24 H24 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 N3 Cu1 N1 86.87(9) . . ? N3 Cu1 Cl2 161.37(7) . . ? N1 Cu1 Cl2 92.24(7) . . ? N3 Cu1 Cl1 87.13(7) . 5_765 ? N1 Cu1 Cl1 172.31(7) . 5_765 ? Cl2 Cu1 Cl1 91.91(3) . 5_765 ? N3 Cu1 Cl1 94.49(7) . . ? N1 Cu1 Cl1 91.36(7) . . ? Cl2 Cu1 Cl1 104.14(3) . . ? Cl1 Cu1 Cl1 93.90(2) 5_765 . ? Cu1 Cl1 Cu1 86.10(2) 5_765 . ? C7 N1 C1 105.6(2) . . ? C7 N1 Cu1 129.0(2) . . ? C1 N1 Cu1 124.64(19) . . ? C7 N2 C2 107.1(2) . . ? C7 N2 C8 125.9(3) . . ? C2 N2 C8 126.8(3) . . ? C18 N3 C19 105.4(3) . . ? C18 N3 Cu1 126.1(2) . . ? C19 N3 Cu1 128.43(17) . . ? C18 N4 C20 105.9(2) . . ? C18 N4 C17' 148.0(4) . . ? C20 N4 C17' 102.5(4) . . ? C18 N4 C17 116.7(4) . . ? C20 N4 C17 136.8(4) . . ? C17' N4 C17 39.9(3) . . ? C10 O1 C9 116.6(2) . . ? C11 O2 C16' 134.7(5) . . ? C11 O2 C16 106.5(3) . . ? C16' O2 C16 32.5(3) . . ? N1 C1 C6 130.6(3) . . ? N1 C1 C2 108.8(3) . . ? C6 C1 C2 120.6(3) . . ? N2 C2 C3 132.4(3) . . ? N2 C2 C1 105.6(2) . . ? C3 C2 C1 121.9(3) . . ? C4 C3 C2 116.5(3) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? C3 C4 C5 122.3(3) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 117.5(3) . . ? C5 C6 H6 121.2 . . ? C1 C6 H6 121.2 . . ? N1 C7 N2 112.8(3) . . ? N1 C7 H7 123.6 . . ? N2 C7 H7 123.6 . . ? N2 C8 C9 112.6(3) . . ? N2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? O1 C9 C8 107.6(2) . . ? O1 C9 H9A 110.2 . . ? C8 C9 H9A 110.2 . . ? O1 C9 H9B 110.2 . . ? C8 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? O1 C10 C15 124.7(3) . . ? O1 C10 C11 115.7(3) . . ? C15 C10 C11 119.6(3) . . ? O2 C11 C12 125.1(3) . . ? O2 C11 C10 115.9(3) . . ? C12 C11 C10 119.0(3) . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.4(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 120.0(3) . . ? C10 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? O2 C16 C17 104.7(4) . . ? O2 C16 H16A 110.8 . . ? C17 C16 H16A 110.8 . . ? O2 C16 H16B 110.8 . . ? C17 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C16 C17 N4 108.5(4) . . ? C16 C17 H17A 110.0 . . ? N4 C17 H17A 110.0 . . ? C16 C17 H17B 110.0 . . ? N4 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? O2 C16' C17' 102.9(6) . . ? O2 C16' H16C 111.2 . . ? C17' C16' H16C 111.2 . . ? O2 C16' H16D 111.2 . . ? C17' C16' H16D 111.2 . . ? H16C C16' H16D 109.1 . . ? C16' C17' N4 100.1(5) . . ? C16' C17' H17C 111.8 . . ? N4 C17' H17C 111.8 . . ? C16' C17' H17D 111.8 . . ? N4 C17' H17D 111.8 . . ? H17C C17' H17D 109.5 . . ? N3 C18 N4 114.0(3) . . ? N3 C18 H18 123.0 . . ? N4 C18 H18 123.0 . . ? N3 C19 C20 108.86(18) . . ? N3 C19 C24 131.14(18) . . ? C20 C19 C24 120.0 . . ? N4 C20 C19 105.8(2) . . ? N4 C20 C21 134.2(2) . . ? C19 C20 C21 120.0 . . ? C20 C21 C22 120.0 . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 120.0 . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 120.0 . . ? C23 C24 H24 120.0 . . ? C19 C24 H24 120.0 . . ? 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 Cu1 Cl1 Cu1 -87.42(7) . . . 5_765 ? N1 Cu1 Cl1 Cu1 -174.38(7) . . . 5_765 ? Cl2 Cu1 Cl1 Cu1 92.96(3) . . . 5_765 ? Cl1 Cu1 Cl1 Cu1 0.0 5_765 . . 5_765 ? N3 Cu1 N1 C7 -77.7(3) . . . . ? Cl2 Cu1 N1 C7 120.9(2) . . . . ? Cl1 Cu1 N1 C7 -116.5(5) 5_765 . . . ? Cl1 Cu1 N1 C7 16.7(3) . . . . ? N3 Cu1 N1 C1 90.9(2) . . . . ? Cl2 Cu1 N1 C1 -70.5(2) . . . . ? Cl1 Cu1 N1 C1 52.1(6) 5_765 . . . ? Cl1 Cu1 N1 C1 -174.7(2) . . . . ? N1 Cu1 N3 C18 76.2(3) . . . . ? Cl2 Cu1 N3 C18 163.9(2) . . . . ? Cl1 Cu1 N3 C18 -108.6(3) 5_765 . . . ? Cl1 Cu1 N3 C18 -14.9(3) . . . . ? N1 Cu1 N3 C19 -107.1(2) . . . . ? Cl2 Cu1 N3 C19 -19.3(4) . . . . ? Cl1 Cu1 N3 C19 68.1(2) 5_765 . . . ? Cl1 Cu1 N3 C19 161.8(2) . . . . ? C7 N1 C1 C6 178.2(3) . . . . ? Cu1 N1 C1 C6 7.3(4) . . . . ? C7 N1 C1 C2 -1.0(3) . . . . ? Cu1 N1 C1 C2 -171.84(19) . . . . ? C7 N2 C2 C3 179.5(3) . . . . ? C8 N2 C2 C3 -6.4(5) . . . . ? C7 N2 C2 C1 -0.1(3) . . . . ? C8 N2 C2 C1 174.0(3) . . . . ? N1 C1 C2 N2 0.7(3) . . . . ? C6 C1 C2 N2 -178.6(3) . . . . ? N1 C1 C2 C3 -178.9(3) . . . . ? C6 C1 C2 C3 1.8(4) . . . . ? N2 C2 C3 C4 178.5(3) . . . . ? C1 C2 C3 C4 -1.9(4) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? N1 C1 C6 C5 -179.6(3) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? C1 N1 C7 N2 1.0(3) . . . . ? Cu1 N1 C7 N2 171.24(19) . . . . ? C2 N2 C7 N1 -0.5(3) . . . . ? C8 N2 C7 N1 -174.8(3) . . . . ? C7 N2 C8 C9 108.6(4) . . . . ? C2 N2 C8 C9 -64.5(4) . . . . ? C10 O1 C9 C8 -179.6(2) . . . . ? N2 C8 C9 O1 -63.0(4) . . . . ? C9 O1 C10 C15 1.4(4) . . . . ? C9 O1 C10 C11 -178.8(3) . . . . ? C16' O2 C11 C12 3.5(7) . . . . ? C16 O2 C11 C12 -15.5(5) . . . . ? C16' O2 C11 C10 -176.7(5) . . . . ? C16 O2 C11 C10 164.3(4) . . . . ? O1 C10 C11 O2 1.9(4) . . . . ? C15 C10 C11 O2 -178.3(3) . . . . ? O1 C10 C11 C12 -178.3(3) . . . . ? C15 C10 C11 C12 1.5(5) . . . . ? O2 C11 C12 C13 178.5(3) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 C14 0.1(6) . . . . ? C12 C13 C14 C15 0.7(6) . . . . ? O1 C10 C15 C14 179.1(3) . . . . ? C11 C10 C15 C14 -0.7(5) . . . . ? C13 C14 C15 C10 -0.4(6) . . . . ? C11 O2 C16 C17 -167.2(4) . . . . ? C16' O2 C16 C17 38.4(6) . . . . ? O2 C16 C17 N4 64.8(6) . . . . ? C18 N4 C17 C16 -111.9(5) . . . . ? C20 N4 C17 C16 78.4(7) . . . . ? C17' N4 C17 C16 39.5(5) . . . . ? C11 O2 C16' C17' -84.6(7) . . . . ? C16 O2 C16' C17' -49.0(5) . . . . ? O2 C16' C17' N4 -81.4(8) . . . . ? C18 N4 C17' C16' 12.0(13) . . . . ? C20 N4 C17' C16' 164.3(5) . . . . ? C17 N4 C17' C16' -41.8(5) . . . . ? C19 N3 C18 N4 0.3(4) . . . . ? Cu1 N3 C18 N4 177.6(2) . . . . ? C20 N4 C18 N3 1.2(4) . . . . ? C17' N4 C18 N3 153.1(9) . . . . ? C17 N4 C18 N3 -171.4(3) . . . . ? C18 N3 C19 C20 -1.7(3) . . . . ? Cu1 N3 C19 C20 -178.94(16) . . . . ? C18 N3 C19 C24 178.7(2) . . . . ? Cu1 N3 C19 C24 1.5(3) . . . . ? C18 N4 C20 C19 -2.2(3) . . . . ? C17' N4 C20 C19 -167.3(4) . . . . ? C17 N4 C20 C19 168.2(4) . . . . ? C18 N4 C20 C21 -179.7(2) . . . . ? C17' N4 C20 C21 15.1(5) . . . . ? C17 N4 C20 C21 -9.3(6) . . . . ? N3 C19 C20 N4 2.4(2) . . . . ? C24 C19 C20 N4 -178.0(2) . . . . ? N3 C19 C20 C21 -179.6(2) . . . . ? C24 C19 C20 C21 0.0 . . . . ? N4 C20 C21 C22 177.3(3) . . . . ? C19 C20 C21 C22 0.0 . . . . ? C20 C21 C22 C23 0.0 . . . . ? C21 C22 C23 C24 0.0 . . . . ? C22 C23 C24 C19 0.0 . . . . ? N3 C19 C24 C23 179.6(3) . . . . ? C20 C19 C24 C23 0.0 . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.442 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.051 _database_code_depnum_ccdc_archive 'CCDC 941768' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_91208b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 Cu N7 O9' _chemical_formula_weight 659.11 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3233(6) _cell_length_b 10.9891(6) _cell_length_c 13.3452(8) _cell_angle_alpha 79.5730(10) _cell_angle_beta 85.1220(10) _cell_angle_gamma 75.5650(10) _cell_volume 1440.66(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5952 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.80 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 682 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8267 _exptl_absorpt_correction_T_max 0.8591 _exptl_absorpt_process_details sadabs _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 7385 _diffrn_reflns_av_R_equivalents 0.0101 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5046 _reflns_number_gt 4580 _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^)+(0.0407P)^2^+0.6026P] 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 5046 _refine_ls_number_parameters 399 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.56464(2) 0.58136(2) 0.644142(16) 0.03188(9) Uani 1 1 d U . . O1 O 0.98352(14) 0.37516(13) 0.93441(10) 0.0427(3) Uani 1 1 d . . . O2 O 1.09241(15) 0.41000(14) 0.75560(11) 0.0449(3) Uani 1 1 d . . . O3 O 0.37293(13) 0.60065(13) 0.68887(11) 0.0379(3) Uani 1 1 d . . . O4 O 0.42497(15) 0.77439(14) 0.70745(11) 0.0448(3) Uani 1 1 d U . . O5 O 0.22421(15) 0.74980(18) 0.74908(14) 0.0625(5) Uani 1 1 d . . . O6 O 0.52188(14) 0.62674(15) 0.49487(11) 0.0443(3) Uani 1 1 d . . . O7 O 0.32743(18) 0.76060(16) 0.49683(13) 0.0610(5) Uani 1 1 d . . . O8 O 0.36996(18) 0.63023(15) 0.39141(12) 0.0607(5) Uani 1 1 d . . . O9 O 0.8497(2) 0.75968(19) 0.78391(16) 0.0810(6) Uani 1 1 d . . . N1 N 0.61539(15) 0.50267(15) 0.78709(12) 0.0337(3) Uani 1 1 d . . . N2 N 0.70117(15) 0.47053(15) 0.93960(12) 0.0340(3) Uani 1 1 d . . . N3 N 0.95641(15) 0.61337(16) 0.59488(12) 0.0353(4) Uani 1 1 d . . . N4 N 0.73875(15) 0.62256(15) 0.60455(12) 0.0342(3) Uani 1 1 d . . . N5 N 0.33858(16) 0.71194(16) 0.71573(12) 0.0376(4) Uani 1 1 d . . . N6 N 0.40428(17) 0.67345(15) 0.46157(12) 0.0360(4) Uani 1 1 d . . . N7 N 0.7922(2) 0.9764(2) 0.75822(17) 0.0648(6) Uani 1 1 d . . . C1 C 0.56749(18) 0.40521(18) 0.85008(14) 0.0326(4) Uani 1 1 d . . . C2 C 0.62179(18) 0.38432(18) 0.94545(14) 0.0340(4) Uani 1 1 d . . . C3 C 0.5939(2) 0.2922(2) 1.02504(16) 0.0456(5) Uani 1 1 d . . . H3 H 0.6315 0.2784 1.0883 0.055 Uiso 1 1 calc R . . C4 C 0.5081(2) 0.2230(2) 1.00521(18) 0.0523(6) Uani 1 1 d . . . H4A H 0.4868 0.1606 1.0564 0.063 Uiso 1 1 calc R . . C5 C 0.4520(2) 0.2435(2) 0.91056(19) 0.0501(5) Uani 1 1 d . . . H5A H 0.3938 0.1949 0.9004 0.060 Uiso 1 1 calc R . . C6 C 0.4803(2) 0.33377(19) 0.83156(17) 0.0409(5) Uani 1 1 d . . . H6 H 0.4428 0.3466 0.7684 0.049 Uiso 1 1 calc R . . C7 C 0.69357(18) 0.53732(18) 0.84456(14) 0.0340(4) Uani 1 1 d . . . H7 H 0.7386 0.6013 0.8216 0.041 Uiso 1 1 calc R . . C8 C 0.7882(2) 0.4771(2) 1.01845(15) 0.0398(5) Uani 1 1 d . . . H8A H 0.7377 0.4791 1.0831 0.048 Uiso 1 1 calc R . . H8B H 0.8193 0.5549 1.0010 0.048 Uiso 1 1 calc R . . C9 C 0.9065(2) 0.3642(2) 1.02882(15) 0.0421(5) Uani 1 1 d . . . H9A H 0.9596 0.3650 1.0852 0.051 Uiso 1 1 calc R . . H9B H 0.8771 0.2854 1.0410 0.051 Uiso 1 1 calc R . . C10 C 1.06315(19) 0.26743(19) 0.90432(16) 0.0383(4) Uani 1 1 d . . . C11 C 1.12103(19) 0.2858(2) 0.80526(15) 0.0392(4) Uani 1 1 d . . . C12 C 1.2001(2) 0.1829(2) 0.76576(19) 0.0514(6) Uani 1 1 d . . . H12 H 1.2372 0.1946 0.6998 0.062 Uiso 1 1 calc R . . C13 C 1.2243(3) 0.0624(2) 0.8240(2) 0.0630(7) Uani 1 1 d . . . H13 H 1.2770 -0.0068 0.7969 0.076 Uiso 1 1 calc R . . C14 C 1.1710(3) 0.0452(2) 0.9209(2) 0.0647(7) Uani 1 1 d . . . H14 H 1.1886 -0.0357 0.9600 0.078 Uiso 1 1 calc R . . C15 C 1.0905(2) 0.1476(2) 0.96203(19) 0.0528(6) Uani 1 1 d . . . H15 H 1.0551 0.1349 1.0285 0.063 Uiso 1 1 calc R . . C16 C 1.1466(2) 0.4342(2) 0.65402(16) 0.0453(5) Uani 1 1 d . . . H16A H 1.1162 0.3854 0.6110 0.054 Uiso 1 1 calc R . . H16B H 1.2436 0.4097 0.6535 0.054 Uiso 1 1 calc R . . C17 C 1.10002(19) 0.5729(2) 0.61547(16) 0.0438(5) Uani 1 1 d . . . H17A H 1.1182 0.6200 0.6653 0.053 Uiso 1 1 calc R . . H17B H 1.1510 0.5944 0.5531 0.053 Uiso 1 1 calc R . . C18 C 0.89475(19) 0.73344(19) 0.54572(14) 0.0354(4) Uani 1 1 d . . . C19 C 0.75791(19) 0.73851(18) 0.55181(14) 0.0335(4) Uani 1 1 d . . . C20 C 0.6665(2) 0.8484(2) 0.50887(16) 0.0422(5) Uani 1 1 d . . . H20 H 0.5750 0.8532 0.5124 0.051 Uiso 1 1 calc R . . C21 C 0.7177(3) 0.9490(2) 0.46123(18) 0.0512(5) Uani 1 1 d . . . H21 H 0.6592 1.0235 0.4321 0.061 Uiso 1 1 calc R . . C22 C 0.8549(3) 0.9427(2) 0.45522(18) 0.0552(6) Uani 1 1 d . . . H22 H 0.8852 1.0131 0.4221 0.066 Uiso 1 1 calc R . . C23 C 0.9462(2) 0.8354(2) 0.49687(17) 0.0477(5) Uani 1 1 d . . . H23 H 1.0376 0.8311 0.4927 0.057 Uiso 1 1 calc R . . C24 C 0.85908(18) 0.55312(19) 0.62904(14) 0.0358(4) Uani 1 1 d . . . H24 H 0.8749 0.4710 0.6661 0.043 Uiso 1 1 calc R . . C25 C 0.8773(3) 0.8631(3) 0.7706(2) 0.0702(7) Uani 1 1 d . . . H25 H 0.9677 0.8624 0.7690 0.084 Uiso 1 1 calc R . . C26 C 0.8354(4) 1.0932(3) 0.7524(3) 0.1028(12) Uani 1 1 d . . . H26A H 0.9314 1.0743 0.7512 0.154 Uiso 1 1 calc R . . H26B H 0.7995 1.1324 0.8108 0.154 Uiso 1 1 calc R . . H26C H 0.8039 1.1503 0.6914 0.154 Uiso 1 1 calc R . . C27 C 0.6510(4) 0.9883(4) 0.7506(3) 0.1062(12) Uani 1 1 d . . . H27A H 0.6351 0.9058 0.7508 0.159 Uiso 1 1 calc R . . H27B H 0.6208 1.0435 0.6884 0.159 Uiso 1 1 calc R . . H27C H 0.6029 1.0235 0.8076 0.159 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 0.02298(13) 0.03770(14) 0.03495(14) -0.00250(9) -0.00491(9) -0.00851(9) O1 0.0401(8) 0.0420(8) 0.0409(8) -0.0072(6) 0.0042(6) -0.0024(6) O2 0.0426(8) 0.0494(9) 0.0381(7) -0.0108(6) 0.0018(6) -0.0013(7) O3 0.0279(7) 0.0369(7) 0.0491(8) -0.0053(6) -0.0038(6) -0.0083(6) O4 0.0457(8) 0.0411(7) 0.0512(8) -0.0105(6) -0.0044(7) -0.0141(6) O5 0.0345(9) 0.0842(13) 0.0686(11) -0.0325(10) 0.0075(8) -0.0031(8) O6 0.0335(7) 0.0583(9) 0.0403(8) -0.0047(7) -0.0051(6) -0.0109(7) O7 0.0664(11) 0.0558(10) 0.0541(10) -0.0210(8) -0.0180(8) 0.0119(8) O8 0.0818(12) 0.0463(9) 0.0535(9) -0.0170(8) -0.0374(9) 0.0034(8) O9 0.1090(17) 0.0579(12) 0.0842(14) -0.0137(10) -0.0177(12) -0.0292(12) N1 0.0280(8) 0.0371(9) 0.0360(8) -0.0035(7) -0.0046(6) -0.0088(7) N2 0.0287(8) 0.0392(9) 0.0355(8) -0.0103(7) -0.0036(6) -0.0069(7) N3 0.0263(8) 0.0480(10) 0.0348(8) -0.0070(7) -0.0027(6) -0.0138(7) N4 0.0260(8) 0.0404(9) 0.0363(8) -0.0033(7) -0.0016(6) -0.0100(7) N5 0.0312(9) 0.0466(10) 0.0332(8) -0.0062(7) -0.0040(7) -0.0056(7) N6 0.0434(9) 0.0335(9) 0.0316(8) -0.0019(7) -0.0079(7) -0.0104(7) N7 0.0682(14) 0.0610(14) 0.0572(13) -0.0045(10) -0.0014(11) -0.0047(11) C1 0.0270(9) 0.0330(10) 0.0367(10) -0.0055(8) -0.0022(7) -0.0048(7) C2 0.0282(9) 0.0360(10) 0.0369(10) -0.0089(8) 0.0005(8) -0.0045(8) C3 0.0472(12) 0.0496(12) 0.0368(11) -0.0011(9) -0.0015(9) -0.0102(10) C4 0.0516(13) 0.0494(13) 0.0539(13) 0.0056(11) 0.0018(11) -0.0197(11) C5 0.0413(12) 0.0440(12) 0.0682(15) -0.0054(11) -0.0024(11) -0.0189(10) C6 0.0342(10) 0.0410(11) 0.0492(12) -0.0073(9) -0.0078(9) -0.0107(9) C7 0.0290(9) 0.0364(10) 0.0375(10) -0.0071(8) -0.0023(8) -0.0087(8) C8 0.0360(10) 0.0531(12) 0.0342(10) -0.0182(9) -0.0031(8) -0.0094(9) C9 0.0351(11) 0.0572(13) 0.0333(10) -0.0081(9) -0.0036(8) -0.0084(9) C10 0.0308(10) 0.0399(11) 0.0456(11) -0.0127(9) -0.0065(8) -0.0056(8) C11 0.0313(10) 0.0452(12) 0.0429(11) -0.0143(9) -0.0073(8) -0.0054(8) C12 0.0473(13) 0.0542(14) 0.0543(13) -0.0238(11) -0.0032(10) -0.0041(10) C13 0.0592(15) 0.0502(15) 0.0821(19) -0.0320(14) -0.0034(14) -0.0022(12) C14 0.0646(16) 0.0382(13) 0.087(2) -0.0069(13) -0.0072(14) -0.0051(12) C15 0.0519(14) 0.0471(13) 0.0555(14) -0.0054(11) -0.0017(11) -0.0068(11) C16 0.0281(10) 0.0684(15) 0.0400(11) -0.0165(10) 0.0005(8) -0.0081(10) C17 0.0258(9) 0.0665(14) 0.0409(11) -0.0056(10) -0.0021(8) -0.0163(9) C18 0.0357(10) 0.0428(11) 0.0320(9) -0.0105(8) -0.0013(8) -0.0139(9) C19 0.0343(10) 0.0383(10) 0.0313(9) -0.0099(8) 0.0022(8) -0.0133(8) C20 0.0398(11) 0.0415(11) 0.0442(11) -0.0108(9) -0.0011(9) -0.0052(9) C21 0.0641(15) 0.0367(12) 0.0515(13) -0.0077(10) -0.0031(11) -0.0091(10) C22 0.0738(17) 0.0450(13) 0.0537(13) -0.0053(11) 0.0012(12) -0.0304(12) C23 0.0496(13) 0.0575(14) 0.0462(12) -0.0110(10) 0.0025(10) -0.0315(11) C24 0.0292(10) 0.0419(11) 0.0368(10) -0.0027(8) -0.0035(8) -0.0113(8) C25 0.0720(18) 0.080(2) 0.0563(15) -0.0088(14) -0.0102(13) -0.0128(16) C26 0.111(3) 0.069(2) 0.121(3) 0.011(2) -0.010(2) -0.025(2) C27 0.084(3) 0.121(3) 0.116(3) -0.029(2) 0.008(2) -0.026(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 N4 1.9678(15) . ? Cu1 O3 1.9884(13) . ? Cu1 N1 2.0021(15) . ? Cu1 O6 2.0229(14) . ? Cu1 O8 2.3768(16) 2_666 ? Cu1 O4 2.4918(15) . ? O1 C10 1.367(2) . ? O1 C9 1.434(2) . ? O2 C11 1.376(3) . ? O2 C16 1.427(2) . ? O3 N5 1.293(2) . ? O4 N5 1.241(2) . ? O5 N5 1.224(2) . ? O6 N6 1.278(2) . ? O7 N6 1.220(2) . ? O8 N6 1.237(2) . ? O8 Cu1 2.3769(16) 2_666 ? O9 C25 1.218(3) . ? N1 C7 1.322(2) . ? N1 C1 1.402(2) . ? N2 C7 1.343(2) . ? N2 C2 1.387(2) . ? N2 C8 1.463(2) . ? N3 C24 1.342(2) . ? N3 C18 1.384(3) . ? N3 C17 1.472(2) . ? N4 C24 1.318(2) . ? N4 C19 1.391(2) . ? N7 C25 1.325(4) . ? N7 C27 1.441(4) . ? N7 C26 1.448(4) . ? C1 C2 1.392(3) . ? C1 C6 1.396(3) . ? C2 C3 1.393(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 H4A 0.9300 . ? C5 C6 1.376(3) . ? C5 H5A 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.504(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.375(3) . ? C10 C11 1.405(3) . ? C11 C12 1.380(3) . ? C12 C13 1.384(4) . ? C12 H12 0.9300 . ? C13 C14 1.361(4) . ? C13 H13 0.9300 . ? C14 C15 1.392(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.487(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.391(3) . ? C18 C19 1.396(3) . ? C19 C20 1.396(3) . ? C20 C21 1.373(3) . ? C20 H20 0.9300 . ? C21 C22 1.398(4) . ? C21 H21 0.9300 . ? C22 C23 1.373(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 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 N4 Cu1 O3 160.84(6) . . ? N4 Cu1 N1 94.06(6) . . ? O3 Cu1 N1 89.16(6) . . ? N4 Cu1 O6 87.66(6) . . ? O3 Cu1 O6 92.69(6) . . ? N1 Cu1 O6 169.24(6) . . ? N4 Cu1 O8 95.81(7) . 2_666 ? O3 Cu1 O8 103.27(6) . 2_666 ? N1 Cu1 O8 85.54(6) . 2_666 ? O6 Cu1 O8 83.72(6) . 2_666 ? N4 Cu1 O4 104.52(6) . . ? O3 Cu1 O4 56.55(5) . . ? N1 Cu1 O4 89.84(6) . . ? O6 Cu1 O4 100.02(5) . . ? O8 Cu1 O4 159.42(6) 2_666 . ? C10 O1 C9 119.06(16) . . ? C11 O2 C16 117.37(16) . . ? N5 O3 Cu1 103.97(10) . . ? N5 O4 Cu1 81.79(10) . . ? N6 O6 Cu1 124.57(12) . . ? N6 O8 Cu1 128.51(12) . 2_666 ? C7 N1 C1 105.32(15) . . ? C7 N1 Cu1 127.42(13) . . ? C1 N1 Cu1 127.11(12) . . ? C7 N2 C2 107.03(15) . . ? C7 N2 C8 126.54(16) . . ? C2 N2 C8 126.10(17) . . ? C24 N3 C18 106.90(16) . . ? C24 N3 C17 128.83(17) . . ? C18 N3 C17 123.75(16) . . ? C24 N4 C19 105.69(15) . . ? C24 N4 Cu1 128.26(13) . . ? C19 N4 Cu1 125.80(13) . . ? O5 N5 O4 123.33(18) . . ? O5 N5 O3 118.98(17) . . ? O4 N5 O3 117.69(15) . . ? O7 N6 O8 120.19(17) . . ? O7 N6 O6 120.97(16) . . ? O8 N6 O6 118.83(17) . . ? C25 N7 C27 120.9(3) . . ? C25 N7 C26 122.1(3) . . ? C27 N7 C26 117.0(3) . . ? C2 C1 C6 120.18(18) . . ? C2 C1 N1 108.59(16) . . ? C6 C1 N1 131.23(18) . . ? N2 C2 C1 106.06(16) . . ? N2 C2 C3 131.48(18) . . ? C1 C2 C3 122.45(18) . . ? C4 C3 C2 116.4(2) . . ? C4 C3 H3 121.8 . . ? C2 C3 H3 121.8 . . ? C3 C4 C5 121.8(2) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C6 C5 C4 121.9(2) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C1 117.3(2) . . ? C5 C6 H6 121.4 . . ? C1 C6 H6 121.4 . . ? N1 C7 N2 112.99(16) . . ? N1 C7 H7 123.5 . . ? N2 C7 H7 123.5 . . ? N2 C8 C9 110.85(16) . . ? N2 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O1 C9 C8 106.21(16) . . ? O1 C9 H9A 110.5 . . ? C8 C9 H9A 110.5 . . ? O1 C9 H9B 110.5 . . ? C8 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? O1 C10 C15 125.92(19) . . ? O1 C10 C11 114.73(18) . . ? C15 C10 C11 119.34(19) . . ? O2 C11 C12 125.4(2) . . ? O2 C11 C10 114.84(17) . . ? C12 C11 C10 119.7(2) . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.7(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C10 C15 C14 119.9(2) . . ? C10 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? O2 C16 C17 107.75(17) . . ? O2 C16 H16A 110.2 . . ? C17 C16 H16A 110.2 . . ? O2 C16 H16B 110.2 . . ? C17 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? N3 C17 C16 113.56(17) . . ? N3 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? N3 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? N3 C18 C23 131.73(19) . . ? N3 C18 C19 106.01(16) . . ? C23 C18 C19 122.2(2) . . ? N4 C19 C18 108.43(17) . . ? N4 C19 C20 131.04(18) . . ? C18 C19 C20 120.52(18) . . ? C21 C20 C19 117.0(2) . . ? C21 C20 H20 121.5 . . ? C19 C20 H20 121.5 . . ? C20 C21 C22 122.0(2) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C23 C22 C21 121.8(2) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C18 116.5(2) . . ? C22 C23 H23 121.8 . . ? C18 C23 H23 121.8 . . ? N4 C24 N3 112.95(18) . . ? N4 C24 H24 123.5 . . ? N3 C24 H24 123.5 . . ? O9 C25 N7 126.9(3) . . ? O9 C25 H25 116.6 . . ? N7 C25 H25 116.6 . . ? N7 C26 H26A 109.5 . . ? N7 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N7 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N7 C27 H27A 109.5 . . ? N7 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N7 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 N4 Cu1 O3 N5 -9.8(2) . . . . ? N1 Cu1 O3 N5 90.18(11) . . . . ? O6 Cu1 O3 N5 -100.43(11) . . . . ? O8 Cu1 O3 N5 175.40(10) 2_666 . . . ? O4 Cu1 O3 N5 -0.18(10) . . . . ? N4 Cu1 O4 N5 176.93(10) . . . . ? O3 Cu1 O4 N5 0.19(10) . . . . ? N1 Cu1 O4 N5 -88.91(11) . . . . ? O6 Cu1 O4 N5 86.76(11) . . . . ? O8 Cu1 O4 N5 -12.1(2) 2_666 . . . ? N4 Cu1 O6 N6 -149.30(15) . . . . ? O3 Cu1 O6 N6 11.53(15) . . . . ? N1 Cu1 O6 N6 111.2(3) . . . . ? O8 Cu1 O6 N6 114.59(15) 2_666 . . . ? O4 Cu1 O6 N6 -44.96(15) . . . . ? N4 Cu1 N1 C7 34.50(17) . . . . ? O3 Cu1 N1 C7 -126.60(16) . . . . ? O6 Cu1 N1 C7 133.4(3) . . . . ? O8 Cu1 N1 C7 130.02(17) 2_666 . . . ? O4 Cu1 N1 C7 -70.05(16) . . . . ? N4 Cu1 N1 C1 -150.67(15) . . . . ? O3 Cu1 N1 C1 48.23(15) . . . . ? O6 Cu1 N1 C1 -51.8(4) . . . . ? O8 Cu1 N1 C1 -55.15(15) 2_666 . . . ? O4 Cu1 N1 C1 104.78(15) . . . . ? O3 Cu1 N4 C24 139.19(19) . . . . ? N1 Cu1 N4 C24 40.00(17) . . . . ? O6 Cu1 N4 C24 -129.36(17) . . . . ? O8 Cu1 N4 C24 -45.92(17) 2_666 . . . ? O4 Cu1 N4 C24 130.89(16) . . . . ? O3 Cu1 N4 C19 -34.3(3) . . . . ? N1 Cu1 N4 C19 -133.49(15) . . . . ? O6 Cu1 N4 C19 57.14(15) . . . . ? O8 Cu1 N4 C19 140.58(15) 2_666 . . . ? O4 Cu1 N4 C19 -42.61(16) . . . . ? Cu1 O4 N5 O5 178.71(18) . . . . ? Cu1 O4 N5 O3 -0.27(14) . . . . ? Cu1 O3 N5 O5 -178.68(15) . . . . ? Cu1 O3 N5 O4 0.35(18) . . . . ? Cu1 O8 N6 O7 -148.79(16) 2_666 . . . ? Cu1 O8 N6 O6 32.4(3) 2_666 . . . ? Cu1 O6 N6 O7 45.5(2) . . . . ? Cu1 O6 N6 O8 -135.65(16) . . . . ? C7 N1 C1 C2 -0.5(2) . . . . ? Cu1 N1 C1 C2 -176.26(12) . . . . ? C7 N1 C1 C6 179.1(2) . . . . ? Cu1 N1 C1 C6 3.4(3) . . . . ? C7 N2 C2 C1 -0.5(2) . . . . ? C8 N2 C2 C1 -174.23(17) . . . . ? C7 N2 C2 C3 179.7(2) . . . . ? C8 N2 C2 C3 5.9(3) . . . . ? C6 C1 C2 N2 -179.05(17) . . . . ? N1 C1 C2 N2 0.6(2) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? N1 C1 C2 C3 -179.53(18) . . . . ? N2 C2 C3 C4 179.1(2) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? N1 C1 C6 C5 -179.8(2) . . . . ? C1 N1 C7 N2 0.2(2) . . . . ? Cu1 N1 C7 N2 175.93(12) . . . . ? C2 N2 C7 N1 0.2(2) . . . . ? C8 N2 C7 N1 173.89(17) . . . . ? C7 N2 C8 C9 -102.8(2) . . . . ? C2 N2 C8 C9 69.8(2) . . . . ? C10 O1 C9 C8 -154.08(16) . . . . ? N2 C8 C9 O1 65.2(2) . . . . ? C9 O1 C10 C15 -8.4(3) . . . . ? C9 O1 C10 C11 172.24(17) . . . . ? C16 O2 C11 C12 1.4(3) . . . . ? C16 O2 C11 C10 -178.96(17) . . . . ? O1 C10 C11 O2 2.3(2) . . . . ? C15 C10 C11 O2 -177.17(19) . . . . ? O1 C10 C11 C12 -178.06(18) . . . . ? C15 C10 C11 C12 2.5(3) . . . . ? O2 C11 C12 C13 178.5(2) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C12 C13 C14 C15 0.9(4) . . . . ? O1 C10 C15 C14 178.4(2) . . . . ? C11 C10 C15 C14 -2.2(3) . . . . ? C13 C14 C15 C10 0.5(4) . . . . ? C11 O2 C16 C17 178.60(16) . . . . ? C24 N3 C17 C16 18.6(3) . . . . ? C18 N3 C17 C16 -170.78(17) . . . . ? O2 C16 C17 N3 -71.0(2) . . . . ? C24 N3 C18 C23 179.6(2) . . . . ? C17 N3 C18 C23 7.3(3) . . . . ? C24 N3 C18 C19 -0.9(2) . . . . ? C17 N3 C18 C19 -173.27(17) . . . . ? C24 N4 C19 C18 0.5(2) . . . . ? Cu1 N4 C19 C18 175.23(12) . . . . ? C24 N4 C19 C20 -179.2(2) . . . . ? Cu1 N4 C19 C20 -4.5(3) . . . . ? N3 C18 C19 N4 0.3(2) . . . . ? C23 C18 C19 N4 179.79(18) . . . . ? N3 C18 C19 C20 -179.94(17) . . . . ? C23 C18 C19 C20 -0.4(3) . . . . ? N4 C19 C20 C21 179.8(2) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 -0.1(4) . . . . ? C21 C22 C23 C18 -0.2(3) . . . . ? N3 C18 C23 C22 179.9(2) . . . . ? C19 C18 C23 C22 0.5(3) . . . . ? C19 N4 C24 N3 -1.2(2) . . . . ? Cu1 N4 C24 N3 -175.70(12) . . . . ? C18 N3 C24 N4 1.4(2) . . . . ? C17 N3 C24 N4 173.17(18) . . . . ? C27 N7 C25 O9 -5.4(5) . . . . ? C26 N7 C25 O9 174.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.529 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 941769' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_100316a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Cu N4 O6 S' _chemical_formula_weight 558.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 9.8299(4) _cell_length_b 11.2063(5) _cell_length_c 11.6827(5) _cell_angle_alpha 102.8160(10) _cell_angle_beta 103.3060(10) _cell_angle_gamma 98.2450(10) _cell_volume 1195.26(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4448 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.98 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 574 _exptl_absorpt_coefficient_mu 1.050 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8019 _exptl_absorpt_correction_T_max 0.8417 _exptl_absorpt_process_details SADABS _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 6047 _diffrn_reflns_av_R_equivalents 0.0094 _diffrn_reflns_av_sigmaI/netI 0.0180 _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 -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4167 _reflns_number_gt 3768 _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^)+(0.1204P)^2^+7.2906P] 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 4167 _refine_ls_number_parameters 301 _refine_ls_number_restraints 146 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.2304 _refine_ls_wR_factor_gt 0.2243 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.324 _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 0.06053(9) 0.38842(8) 0.35360(9) 0.0334(4) Uani 1 1 d . . . S1 S -0.08006(19) 0.56572(17) 0.34894(17) 0.0326(5) Uani 1 1 d . . . O1 O 0.2724(8) -0.0540(7) 0.3501(9) 0.077(2) Uani 1 1 d D . . O2 O 0.5080(6) 0.1032(5) 0.3820(6) 0.0473(14) Uani 1 1 d . . . O3 O -0.1328(6) 0.4267(5) 0.3221(6) 0.0450(14) Uani 1 1 d . . . O4 O 0.0781(6) 0.5737(5) 0.3774(6) 0.0409(13) Uani 1 1 d . . . O5 O -0.1186(7) 0.6302(6) 0.4558(6) 0.0542(17) Uani 1 1 d . . . O6 O -0.1324(7) 0.6125(6) 0.2462(6) 0.0529(16) Uani 1 1 d . . . N3 N 0.4769(6) 0.3503(6) 0.3763(6) 0.0320(13) Uani 1 1 d . . . N4 N 0.2565(6) 0.3841(6) 0.3442(6) 0.0336(14) Uani 1 1 d . . . N2 N -0.0033(7) -0.0014(5) 0.2339(6) 0.107(4) Uani 1 1 d GDU . . C7 C 0.0618(7) 0.1167(6) 0.3179(6) 0.087(3) Uani 1 1 d GDU . . H7 H 0.1350 0.1313 0.3890 0.104 Uiso 1 1 calc R . . N1 N -0.0045(7) 0.2086(5) 0.2744(6) 0.072(2) Uani 1 1 d GDU . . C1 C -0.1105(5) 0.1473(4) 0.1634(5) 0.075(2) Uani 1 1 d GDU . . C2 C -0.1098(6) 0.0175(4) 0.1384(5) 0.088(2) Uani 1 1 d GDU . . C3 C -0.2023(8) -0.0632(5) 0.0363(6) 0.100(3) Uani 1 1 d GDU . . H3 H -0.2020 -0.1483 0.0198 0.120 Uiso 1 1 calc R . . C4 C -0.2973(8) -0.0183(7) -0.0433(6) 0.106(3) Uani 1 1 d GDU . . H4 H -0.3605 -0.0733 -0.1131 0.127 Uiso 1 1 calc R . . C5 C -0.2977(8) 0.1088(8) -0.0186(6) 0.098(3) Uani 1 1 d GDU . . H5 H -0.3612 0.1389 -0.0719 0.118 Uiso 1 1 calc R . . C6 C -0.2031(7) 0.1910(6) 0.0857(6) 0.084(2) Uani 1 1 d GDU . . H6 H -0.2035 0.2760 0.1022 0.100 Uiso 1 1 calc R . . C8 C 0.0323(11) -0.1227(6) 0.2117(9) 0.128(6) Uani 1 1 d GDU . . H8A H 0.0810 -0.1347 0.1479 0.154 Uiso 1 1 calc R . . H8B H -0.0525 -0.1883 0.1885 0.154 Uiso 1 1 calc R . . C9 C 0.1287(12) -0.1219(14) 0.3311(12) 0.100(4) Uani 1 1 d DU . . H9A H 0.0904 -0.0837 0.3965 0.120 Uiso 1 1 calc R . . H9B H 0.1315 -0.2073 0.3342 0.120 Uiso 1 1 calc R . . C10 C 0.3804(12) -0.1051(9) 0.3237(9) 0.059(3) Uani 1 1 d . . . C11 C 0.5090(11) -0.0205(8) 0.3410(8) 0.051(2) Uani 1 1 d . . . C12 C 0.6272(14) -0.0660(11) 0.3180(11) 0.068(3) Uani 1 1 d . . . H12 H 0.7121 -0.0110 0.3280 0.081 Uiso 1 1 calc R . . C13 C 0.617(2) -0.1951(13) 0.2797(12) 0.092(5) Uani 1 1 d . . . H13 H 0.6976 -0.2249 0.2673 0.110 Uiso 1 1 calc R . . C14 C 0.496(2) -0.2776(11) 0.2602(12) 0.086(4) Uani 1 1 d . . . H14 H 0.4910 -0.3631 0.2336 0.103 Uiso 1 1 calc R . . C15 C 0.3751(18) -0.2316(10) 0.2812(11) 0.082(4) Uani 1 1 d . . . H15 H 0.2896 -0.2878 0.2660 0.098 Uiso 1 1 calc R . . C16 C 0.6293(9) 0.1915(8) 0.3826(9) 0.046(2) Uani 1 1 d . . . H16A H 0.6359 0.1851 0.2999 0.055 Uiso 1 1 calc R . . H16B H 0.7164 0.1750 0.4294 0.055 Uiso 1 1 calc R . . C17 C 0.6099(8) 0.3199(7) 0.4392(8) 0.0400(18) Uani 1 1 d . . . H17A H 0.6106 0.3263 0.5235 0.048 Uiso 1 1 calc R . . H17B H 0.6902 0.3812 0.4390 0.048 Uiso 1 1 calc R . . C18 C 0.4411(8) 0.3679(7) 0.2605(7) 0.0335(16) Uani 1 1 d . . . C19 C 0.3025(8) 0.3894(7) 0.2400(7) 0.0343(16) Uani 1 1 d . . . C20 C 0.2330(10) 0.4099(8) 0.1314(8) 0.047(2) Uani 1 1 d . . . H20 H 0.1408 0.4250 0.1180 0.057 Uiso 1 1 calc R . . C21 C 0.3064(13) 0.4071(9) 0.0436(9) 0.060(3) Uani 1 1 d . . . H21 H 0.2631 0.4209 -0.0306 0.072 Uiso 1 1 calc R . . C22 C 0.4465(12) 0.3836(10) 0.0646(9) 0.056(2) Uani 1 1 d . . . H22 H 0.4921 0.3801 0.0028 0.068 Uiso 1 1 calc R . . C23 C 0.5165(10) 0.3659(8) 0.1723(8) 0.047(2) Uani 1 1 d . . . H23 H 0.6097 0.3530 0.1866 0.057 Uiso 1 1 calc R . . C24 C 0.3630(8) 0.3599(7) 0.4205(7) 0.0334(16) Uani 1 1 d . . . H24 H 0.3600 0.3503 0.4970 0.040 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 0.0257(5) 0.0271(5) 0.0472(6) 0.0089(4) 0.0092(4) 0.0073(4) S1 0.0304(9) 0.0317(10) 0.0407(10) 0.0155(8) 0.0104(8) 0.0116(7) O1 0.051(4) 0.050(4) 0.125(7) 0.044(4) 0.004(4) -0.001(3) O2 0.043(3) 0.034(3) 0.064(4) 0.010(3) 0.015(3) 0.009(2) O3 0.026(3) 0.035(3) 0.075(4) 0.018(3) 0.012(3) 0.007(2) O4 0.029(3) 0.031(3) 0.060(4) 0.013(2) 0.009(2) 0.003(2) O5 0.069(4) 0.063(4) 0.053(4) 0.027(3) 0.030(3) 0.042(3) O6 0.060(4) 0.057(4) 0.048(3) 0.027(3) 0.009(3) 0.022(3) N3 0.024(3) 0.033(3) 0.037(3) 0.008(3) 0.007(2) 0.004(2) N4 0.031(3) 0.031(3) 0.040(3) 0.009(3) 0.012(3) 0.008(3) N2 0.099(6) 0.072(5) 0.142(7) 0.019(5) 0.030(5) 0.017(5) C7 0.072(4) 0.060(4) 0.121(5) 0.023(4) 0.015(4) 0.012(4) N1 0.054(4) 0.046(3) 0.112(4) 0.015(3) 0.021(3) 0.013(3) C1 0.067(3) 0.066(3) 0.092(3) 0.010(3) 0.033(3) 0.008(3) C2 0.082(4) 0.071(3) 0.104(4) 0.006(3) 0.032(3) 0.010(3) C3 0.098(4) 0.082(4) 0.107(4) 0.006(3) 0.029(3) 0.009(3) C4 0.106(4) 0.094(4) 0.104(4) 0.011(3) 0.025(3) 0.009(4) C5 0.100(4) 0.092(4) 0.092(4) 0.015(3) 0.024(3) 0.006(4) C6 0.083(4) 0.082(4) 0.083(4) 0.017(3) 0.028(3) 0.006(3) C8 0.126(8) 0.121(8) 0.136(8) 0.036(6) 0.032(6) 0.024(6) C9 0.105(7) 0.087(6) 0.103(6) 0.053(5) 0.009(5) -0.007(5) C10 0.070(7) 0.039(5) 0.055(6) 0.020(4) -0.009(5) 0.001(5) C11 0.065(6) 0.037(5) 0.046(5) 0.010(4) 0.007(4) 0.016(4) C12 0.083(8) 0.055(6) 0.073(7) 0.015(5) 0.026(6) 0.034(6) C13 0.143(14) 0.073(9) 0.077(8) 0.014(7) 0.047(9) 0.062(10) C14 0.142(14) 0.042(6) 0.068(8) 0.013(5) 0.021(8) 0.020(8) C15 0.125(11) 0.039(6) 0.061(7) 0.017(5) -0.005(7) -0.001(6) C16 0.035(4) 0.043(5) 0.061(5) 0.015(4) 0.011(4) 0.015(4) C17 0.025(4) 0.039(4) 0.052(5) 0.011(4) 0.003(3) 0.004(3) C18 0.034(4) 0.027(4) 0.038(4) 0.006(3) 0.012(3) 0.003(3) C19 0.032(4) 0.029(4) 0.040(4) 0.008(3) 0.009(3) 0.004(3) C20 0.045(5) 0.043(5) 0.048(5) 0.015(4) 0.001(4) 0.006(4) C21 0.082(7) 0.052(6) 0.037(5) 0.014(4) 0.004(5) -0.004(5) C22 0.067(6) 0.058(6) 0.044(5) 0.014(4) 0.022(5) 0.002(5) C23 0.045(5) 0.044(5) 0.056(5) 0.010(4) 0.025(4) 0.003(4) C24 0.031(4) 0.030(4) 0.037(4) 0.006(3) 0.010(3) 0.006(3) _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 N4 1.962(6) . ? Cu1 N1 1.964(5) . ? Cu1 O3 1.979(5) . ? Cu1 O4 2.009(5) . ? Cu1 O5 2.232(6) 2_566 ? S1 O6 1.432(6) . ? S1 O5 1.456(6) . ? S1 O4 1.499(6) . ? S1 O3 1.507(6) . ? O1 C10 1.340(14) . ? O1 C9 1.448(10) . ? O2 C11 1.365(10) . ? O2 C16 1.434(11) . ? O5 Cu1 2.232(6) 2_566 ? N3 C24 1.344(10) . ? N3 C18 1.382(10) . ? N3 C17 1.471(9) . ? N4 C24 1.313(10) . ? N4 C19 1.403(10) . ? N2 C2 1.4200 . ? N2 C7 1.4200 . ? N2 C8 1.4357 . ? C7 N1 1.4200 . ? C7 H7 0.9300 . ? N1 C1 1.4200 . ? C1 C6 1.3552 . ? C1 C2 1.4200 . ? C2 C3 1.3624 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.492(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.383(15) . ? C10 C11 1.411(15) . ? C11 C12 1.391(15) . ? C12 C13 1.398(17) . ? C12 H12 0.9300 . ? C13 C14 1.34(2) . ? C13 H13 0.9300 . ? C14 C15 1.41(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.503(12) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.393(11) . ? C18 C23 1.399(11) . ? C19 C20 1.379(11) . ? C20 C21 1.381(14) . ? C20 H20 0.9300 . ? C21 C22 1.416(16) . ? C21 H21 0.9300 . ? C22 C23 1.360(14) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 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 Cu1 N1 92.1(3) . . ? N4 Cu1 O3 160.2(3) . . ? N1 Cu1 O3 95.2(3) . . ? N4 Cu1 O4 96.3(2) . . ? N1 Cu1 O4 159.0(3) . . ? O3 Cu1 O4 71.0(2) . . ? N4 Cu1 O5 90.4(3) . 2_566 ? N1 Cu1 O5 96.0(3) . 2_566 ? O3 Cu1 O5 107.0(3) . 2_566 ? O4 Cu1 O5 103.1(2) . 2_566 ? O6 S1 O5 111.1(4) . . ? O6 S1 O4 112.1(4) . . ? O5 S1 O4 110.4(4) . . ? O6 S1 O3 112.0(4) . . ? O5 S1 O3 109.9(4) . . ? O4 S1 O3 100.8(3) . . ? C10 O1 C9 125.4(10) . . ? C11 O2 C16 117.0(7) . . ? S1 O3 Cu1 94.6(3) . . ? S1 O4 Cu1 93.6(3) . . ? S1 O5 Cu1 129.6(3) . 2_566 ? C24 N3 C18 107.0(6) . . ? C24 N3 C17 125.2(7) . . ? C18 N3 C17 127.7(7) . . ? C24 N4 C19 105.9(6) . . ? C24 N4 Cu1 129.8(5) . . ? C19 N4 Cu1 123.8(5) . . ? C2 N2 C7 108.0 . . ? C2 N2 C8 115.5 . . ? C7 N2 C8 135.0 . . ? N2 C7 N1 108.0 . . ? N2 C7 H7 126.0 . . ? N1 C7 H7 126.0 . . ? C1 N1 C7 108.0 . . ? C1 N1 Cu1 129.0(3) . . ? C7 N1 Cu1 122.8(3) . . ? C6 C1 C2 120.1 . . ? C6 C1 N1 131.9 . . ? C2 C1 N1 108.0 . . ? C3 C2 C1 120.0 . . ? C3 C2 N2 132.0 . . ? C1 C2 N2 108.0 . . ? C2 C3 C4 119.9 . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 120.1 . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N2 C8 C9 103.7(8) . . ? N2 C8 H8A 111.0 . . ? C9 C8 H8A 111.0 . . ? N2 C8 H8B 111.0 . . ? C9 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? O1 C9 C8 112.0(9) . . ? O1 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? O1 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O1 C10 C15 125.6(11) . . ? O1 C10 C11 116.0(8) . . ? C15 C10 C11 118.5(12) . . ? O2 C11 C12 124.3(10) . . ? O2 C11 C10 116.1(9) . . ? C12 C11 C10 119.6(9) . . ? C11 C12 C13 119.4(13) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 122.4(14) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C13 C14 C15 118.3(11) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C10 C15 C14 121.9(13) . . ? C10 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? O2 C16 C17 107.6(7) . . ? O2 C16 H16A 110.2 . . ? C17 C16 H16A 110.2 . . ? O2 C16 H16B 110.2 . . ? C17 C16 H16B 110.2 . . ? H16A C16 H16B 108.5 . . ? N3 C17 C16 113.6(7) . . ? N3 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? N3 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? N3 C18 C19 106.3(6) . . ? N3 C18 C23 131.9(8) . . ? C19 C18 C23 121.8(8) . . ? C20 C19 C18 121.5(8) . . ? C20 C19 N4 130.6(8) . . ? C18 C19 N4 107.9(7) . . ? C19 C20 C21 117.1(9) . . ? C19 C20 H20 121.5 . . ? C21 C20 H20 121.5 . . ? C20 C21 C22 121.1(9) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 122.0(9) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C18 116.5(9) . . ? C22 C23 H23 121.7 . . ? C18 C23 H23 121.7 . . ? N4 C24 N3 112.8(7) . . ? N4 C24 H24 123.6 . . ? N3 C24 H24 123.6 . . ? 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 O6 S1 O3 Cu1 120.3(4) . . . . ? O5 S1 O3 Cu1 -115.6(3) . . . . ? O4 S1 O3 Cu1 1.0(4) . . . . ? N4 Cu1 O3 S1 -52.9(9) . . . . ? N1 Cu1 O3 S1 -164.4(3) . . . . ? O4 Cu1 O3 S1 -0.7(3) . . . . ? O5 Cu1 O3 S1 97.6(3) 2_566 . . . ? O6 S1 O4 Cu1 -120.2(3) . . . . ? O5 S1 O4 Cu1 115.2(3) . . . . ? O3 S1 O4 Cu1 -0.9(4) . . . . ? N4 Cu1 O4 S1 165.1(3) . . . . ? N1 Cu1 O4 S1 51.9(9) . . . . ? O3 Cu1 O4 S1 0.7(3) . . . . ? O5 Cu1 O4 S1 -103.0(3) 2_566 . . . ? O6 S1 O5 Cu1 -175.9(5) . . . 2_566 ? O4 S1 O5 Cu1 -50.8(6) . . . 2_566 ? O3 S1 O5 Cu1 59.5(6) . . . 2_566 ? N1 Cu1 N4 C24 -87.4(7) . . . . ? O3 Cu1 N4 C24 160.6(7) . . . . ? O4 Cu1 N4 C24 111.9(7) . . . . ? O5 Cu1 N4 C24 8.6(7) 2_566 . . . ? N1 Cu1 N4 C19 82.5(6) . . . . ? O3 Cu1 N4 C19 -29.5(11) . . . . ? O4 Cu1 N4 C19 -78.2(6) . . . . ? O5 Cu1 N4 C19 178.6(6) 2_566 . . . ? C2 N2 C7 N1 0.0 . . . . ? C8 N2 C7 N1 164.5 . . . . ? N2 C7 N1 C1 0.0 . . . . ? N2 C7 N1 Cu1 -175.0(5) . . . . ? N4 Cu1 N1 C1 -119.5(4) . . . . ? O3 Cu1 N1 C1 42.1(4) . . . . ? O4 Cu1 N1 C1 -5.6(10) . . . . ? O5 Cu1 N1 C1 149.9(4) 2_566 . . . ? N4 Cu1 N1 C7 54.3(4) . . . . ? O3 Cu1 N1 C7 -144.1(4) . . . . ? O4 Cu1 N1 C7 168.2(6) . . . . ? O5 Cu1 N1 C7 -36.3(4) 2_566 . . . ? C7 N1 C1 C6 180.0 . . . . ? Cu1 N1 C1 C6 -5.4(5) . . . . ? C7 N1 C1 C2 0.0 . . . . ? Cu1 N1 C1 C2 174.6(5) . . . . ? C6 C1 C2 C3 0.0 . . . . ? N1 C1 C2 C3 180.0 . . . . ? C6 C1 C2 N2 180.0 . . . . ? N1 C1 C2 N2 0.0 . . . . ? C7 N2 C2 C3 180.0 . . . . ? C8 N2 C2 C3 12.1 . . . . ? C7 N2 C2 C1 0.0 . . . . ? C8 N2 C2 C1 -167.9 . . . . ? C1 C2 C3 C4 0.0 . . . . ? N2 C2 C3 C4 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? N1 C1 C6 C5 180.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C2 N2 C8 C9 -172.3(8) . . . . ? C7 N2 C8 C9 24.0(8) . . . . ? C10 O1 C9 C8 -94.4(14) . . . . ? N2 C8 C9 O1 -78.7(13) . . . . ? C9 O1 C10 C15 -4.2(17) . . . . ? C9 O1 C10 C11 175.4(9) . . . . ? C16 O2 C11 C12 10.3(13) . . . . ? C16 O2 C11 C10 -170.8(8) . . . . ? O1 C10 C11 O2 -0.2(13) . . . . ? C15 C10 C11 O2 179.5(9) . . . . ? O1 C10 C11 C12 178.7(9) . . . . ? C15 C10 C11 C12 -1.6(15) . . . . ? O2 C11 C12 C13 178.0(10) . . . . ? C10 C11 C12 C13 -0.9(16) . . . . ? C11 C12 C13 C14 2(2) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? O1 C10 C15 C14 -177.5(11) . . . . ? C11 C10 C15 C14 2.9(16) . . . . ? C13 C14 C15 C10 -1.6(19) . . . . ? C11 O2 C16 C17 -176.0(7) . . . . ? C24 N3 C17 C16 108.9(9) . . . . ? C18 N3 C17 C16 -67.4(10) . . . . ? O2 C16 C17 N3 -57.5(9) . . . . ? C24 N3 C18 C19 0.7(8) . . . . ? C17 N3 C18 C19 177.5(7) . . . . ? C24 N3 C18 C23 -178.7(8) . . . . ? C17 N3 C18 C23 -1.8(13) . . . . ? N3 C18 C19 C20 -179.5(7) . . . . ? C23 C18 C19 C20 -0.1(12) . . . . ? N3 C18 C19 N4 -0.2(8) . . . . ? C23 C18 C19 N4 179.3(7) . . . . ? C24 N4 C19 C20 178.9(8) . . . . ? Cu1 N4 C19 C20 6.9(11) . . . . ? C24 N4 C19 C18 -0.4(8) . . . . ? Cu1 N4 C19 C18 -172.4(5) . . . . ? C18 C19 C20 C21 0.5(12) . . . . ? N4 C19 C20 C21 -178.7(8) . . . . ? C19 C20 C21 C22 0.3(14) . . . . ? C20 C21 C22 C23 -1.7(15) . . . . ? C21 C22 C23 C18 2.1(14) . . . . ? N3 C18 C23 C22 178.1(8) . . . . ? C19 C18 C23 C22 -1.2(12) . . . . ? C19 N4 C24 N3 0.9(8) . . . . ? Cu1 N4 C24 N3 172.2(5) . . . . ? C18 N3 C24 N4 -1.0(8) . . . . ? C17 N3 C24 N4 -178.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.407 _refine_diff_density_min -1.308 _refine_diff_density_rms 0.141 _database_code_depnum_ccdc_archive 'CCDC 941770' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_100112c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H40 Co N6 O8' _chemical_formula_weight 767.69 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 12.7947(5) _cell_length_b 16.9353(7) _cell_length_c 18.0105(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.7400(10) _cell_angle_gamma 90.00 _cell_volume 3774.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8133 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.79 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1604 _exptl_absorpt_coefficient_mu 0.514 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9087 _exptl_absorpt_correction_T_max 0.9315 _exptl_absorpt_process_details sadabs _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 19055 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6654 _reflns_number_gt 5152 _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^)+(0.0755P)^2^+2.2058P] 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 6654 _refine_ls_number_parameters 482 _refine_ls_number_restraints 93 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1424 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.128 _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 1.00848(3) 0.17260(2) 0.25130(2) 0.03858(15) Uani 1 1 d U . . O1 O 0.95634(17) 0.47533(13) 0.08074(13) 0.0542(6) Uani 1 1 d . . . O2 O 1.14192(18) 0.49023(14) 0.18163(13) 0.0590(6) Uani 1 1 d . . . O3 O 0.93760(17) 0.14109(13) 0.33908(11) 0.0472(5) Uani 1 1 d . . . O4 O 1.09604(17) 0.08878(13) 0.34414(12) 0.0519(5) Uani 1 1 d . . . O5 O 0.9659(2) 0.07131(14) 0.18414(13) 0.0692(7) Uani 1 1 d . . . O6 O 1.0791(2) 0.15161(15) 0.15032(13) 0.0599(6) Uani 1 1 d U . . N1 N 0.8969(2) 0.24764(15) 0.18072(14) 0.0460(6) Uani 1 1 d . . . N2 N 0.83213(19) 0.33324(14) 0.08647(14) 0.0433(6) Uani 1 1 d . . . N3 N 1.2283(2) 0.36129(16) 0.28706(15) 0.0501(6) Uani 1 1 d . . . N4 N 1.1184(2) 0.26096(15) 0.29271(14) 0.0470(6) Uani 1 1 d . . . C1 C 0.7990(3) 0.2766(2) 0.18925(19) 0.0512(8) Uani 1 1 d . . . C2 C 0.7573(3) 0.3301(2) 0.12977(19) 0.0519(8) Uani 1 1 d . . . C3 C 0.6592(3) 0.3672(3) 0.1222(3) 0.0868(15) Uani 1 1 d . . . H3 H 0.6323 0.4030 0.0829 0.104 Uiso 1 1 calc R . . C4 C 0.6036(4) 0.3490(4) 0.1751(4) 0.141(3) Uani 1 1 d . . . H4 H 0.5362 0.3717 0.1710 0.169 Uiso 1 1 calc R . . C5 C 0.6462(4) 0.2963(4) 0.2360(4) 0.140(3) Uani 1 1 d . . . H5 H 0.6071 0.2864 0.2720 0.168 Uiso 1 1 calc R . . C6 C 0.7430(3) 0.2596(3) 0.2433(3) 0.0836(14) Uani 1 1 d . . . H6 H 0.7703 0.2245 0.2833 0.100 Uiso 1 1 calc R . . C7 C 0.9120(2) 0.28322(19) 0.11942(17) 0.0470(7) Uani 1 1 d . . . H7 H 0.9724 0.2746 0.1006 0.056 Uiso 1 1 calc R . . C8 C 0.8282(3) 0.37979(19) 0.01717(17) 0.0502(8) Uani 1 1 d . . . H8A H 0.7574 0.3735 -0.0181 0.060 Uiso 1 1 calc R . . H8B H 0.8812 0.3591 -0.0078 0.060 Uiso 1 1 calc R . . C9 C 0.8494(2) 0.46611(19) 0.03258(19) 0.0521(8) Uani 1 1 d . . . H9A H 0.8427 0.4942 -0.0154 0.063 Uiso 1 1 calc R . . H9B H 0.7972 0.4878 0.0578 0.063 Uiso 1 1 calc R . . C10 C 0.9892(3) 0.5514(2) 0.1011(2) 0.0549(8) Uani 1 1 d . . . C11 C 1.0892(3) 0.5590(2) 0.1557(2) 0.0561(8) Uani 1 1 d . . . C12 C 1.1291(4) 0.6339(2) 0.1786(2) 0.0734(11) Uani 1 1 d . . . H12 H 1.1953 0.6395 0.2145 0.088 Uiso 1 1 calc R . . C13 C 1.0701(4) 0.7003(3) 0.1478(3) 0.0872(13) Uani 1 1 d . . . H13 H 1.0972 0.7503 0.1631 0.105 Uiso 1 1 calc R . . C14 C 0.9730(4) 0.6928(2) 0.0956(3) 0.0888(14) Uani 1 1 d . . . H14 H 0.9336 0.7377 0.0761 0.107 Uiso 1 1 calc R . . C15 C 0.9320(3) 0.6181(2) 0.0710(3) 0.0730(11) Uani 1 1 d . . . H15 H 0.8663 0.6133 0.0345 0.088 Uiso 1 1 calc R . . C16 C 1.2415(3) 0.4972(2) 0.2396(2) 0.0622(10) Uani 1 1 d . . . H16A H 1.2281 0.5179 0.2866 0.075 Uiso 1 1 calc R . . H16B H 1.2899 0.5331 0.2227 0.075 Uiso 1 1 calc R . . C17 C 1.2912(3) 0.4168(2) 0.2536(2) 0.0606(9) Uani 1 1 d . . . H17A H 1.2991 0.3956 0.2053 0.073 Uiso 1 1 calc R . . H17B H 1.3630 0.4217 0.2878 0.073 Uiso 1 1 calc R . . C18 C 1.2188(2) 0.3592(2) 0.36207(18) 0.0489(7) Uani 1 1 d . . . C19 C 1.1501(2) 0.29615(18) 0.36522(17) 0.0443(7) Uani 1 1 d . . . C20 C 1.1227(3) 0.2781(2) 0.43323(18) 0.0532(8) Uani 1 1 d . . . H20 H 1.0761 0.2366 0.4358 0.064 Uiso 1 1 calc R . . C21 C 1.1670(3) 0.3237(2) 0.4964(2) 0.0657(10) Uani 1 1 d . . . H21 H 1.1504 0.3128 0.5426 0.079 Uiso 1 1 calc R . . C22 C 1.2367(3) 0.3864(3) 0.4926(2) 0.0743(11) Uani 1 1 d . . . H22 H 1.2655 0.4160 0.5365 0.089 Uiso 1 1 calc R . . C23 C 1.2635(3) 0.4053(2) 0.4259(2) 0.0663(10) Uani 1 1 d . . . H23 H 1.3096 0.4471 0.4235 0.080 Uiso 1 1 calc R . . C24 C 1.1666(3) 0.3023(2) 0.24924(18) 0.0512(8) Uani 1 1 d . . . H24 H 1.1587 0.2918 0.1974 0.061 Uiso 1 1 calc R . . C25 C 1.0134(2) 0.09385(17) 0.36886(15) 0.0397(6) Uani 1 1 d . . . C26 C 1.0053(2) 0.04475(16) 0.43629(15) 0.0358(6) Uani 1 1 d . . . C27 C 1.0772(2) -0.01719(16) 0.46047(15) 0.0375(6) Uani 1 1 d . . . H27 H 1.1289 -0.0289 0.4340 0.045 Uiso 1 1 calc R . . C28 C 0.9282(2) 0.06156(17) 0.47563(16) 0.0385(6) Uani 1 1 d . . . H28 H 0.8797 0.1027 0.4593 0.046 Uiso 1 1 calc R . . C29 C 1.0195(3) 0.0918(2) 0.13810(19) 0.0527(8) Uani 1 1 d . . . C30 C 1.0105(3) 0.04403(18) 0.06654(17) 0.0484(8) Uani 1 1 d . . . C31 C 0.9537(3) -0.02669(19) 0.05725(18) 0.0528(8) Uani 1 1 d . . . H31 H 0.9226 -0.0448 0.0955 0.063 Uiso 1 1 calc R . . C32 C 0.9436(3) -0.07034(19) -0.00982(19) 0.0545(8) Uani 1 1 d . . . H32 H 0.9054 -0.1177 -0.0163 0.065 Uiso 1 1 calc R . . N5 N 0.3426(4) 0.1965(3) 0.0591(3) 0.1266(17) Uani 1 1 d DU . . O7 O 0.2684(5) 0.3085(3) 0.0874(3) 0.167(2) Uani 1 1 d DU . . C33 C 0.3062(8) 0.2444(5) 0.1080(4) 0.174(3) Uani 1 1 d DU . . H33 H 0.3106 0.2275 0.1578 0.208 Uiso 1 1 calc R . . C34 C 0.3850(8) 0.1192(5) 0.0794(5) 0.197(4) Uani 1 1 d DU . . H34A H 0.4599 0.1229 0.1064 0.295 Uiso 1 1 calc R . . H34B H 0.3781 0.0883 0.0336 0.295 Uiso 1 1 calc R . . H34C H 0.3455 0.0943 0.1117 0.295 Uiso 1 1 calc R . . C35 C 0.3328(8) 0.2208(5) -0.0192(4) 0.202(4) Uani 1 1 d DU . . H35A H 0.2859 0.2658 -0.0307 0.303 Uiso 1 1 calc R . . H35B H 0.3030 0.1783 -0.0533 0.303 Uiso 1 1 calc R . . H35C H 0.4028 0.2344 -0.0255 0.303 Uiso 1 1 calc R . . N6 N 0.6470(4) 0.9893(3) 0.1990(3) 0.1367(19) Uani 1 1 d DU . . O8 O 0.6956(10) 0.9354(7) 0.1011(6) 0.335(5) Uani 1 1 d DU . . C36 C 0.7236(8) 0.9802(7) 0.1557(6) 0.264(6) Uani 1 1 d DU . . H36 H 0.7899 1.0061 0.1677 0.317 Uiso 1 1 calc R . . C37 C 0.6760(7) 1.0443(5) 0.2631(5) 0.211(4) Uani 1 1 d DU . . H37A H 0.7478 1.0329 0.2932 0.317 Uiso 1 1 calc R . . H37B H 0.6261 1.0390 0.2945 0.317 Uiso 1 1 calc R . . H37C H 0.6733 1.0973 0.2438 0.317 Uiso 1 1 calc R . . C38 C 0.5528(6) 0.9460(5) 0.1886(5) 0.189(4) Uani 1 1 d DU . . H38A H 0.4997 0.9661 0.1451 0.284 Uiso 1 1 calc R . . H38B H 0.5260 0.9502 0.2336 0.284 Uiso 1 1 calc R . . H38C H 0.5673 0.8916 0.1800 0.284 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 0.0430(2) 0.0391(2) 0.0322(2) 0.00464(15) 0.00688(16) 0.00099(16) O1 0.0425(11) 0.0486(13) 0.0650(14) 0.0093(11) 0.0018(10) -0.0059(10) O2 0.0550(13) 0.0549(14) 0.0591(14) 0.0048(11) -0.0003(11) -0.0157(11) O3 0.0474(12) 0.0513(12) 0.0409(11) 0.0141(10) 0.0076(9) 0.0058(10) O4 0.0546(13) 0.0591(14) 0.0467(12) 0.0130(10) 0.0212(10) 0.0057(11) O5 0.110(2) 0.0551(15) 0.0439(13) -0.0049(11) 0.0217(14) -0.0036(14) O6 0.0602(14) 0.0665(15) 0.0531(13) -0.0203(12) 0.0149(10) 0.0008(12) N1 0.0449(14) 0.0480(15) 0.0428(14) 0.0111(11) 0.0071(11) 0.0053(12) N2 0.0405(13) 0.0470(14) 0.0385(13) 0.0125(11) 0.0030(11) -0.0023(11) N3 0.0428(14) 0.0575(16) 0.0459(15) 0.0021(12) 0.0038(11) -0.0108(12) N4 0.0505(15) 0.0473(15) 0.0399(13) 0.0013(11) 0.0053(11) -0.0049(12) C1 0.0461(17) 0.058(2) 0.0493(18) 0.0147(15) 0.0117(14) 0.0066(15) C2 0.0419(16) 0.059(2) 0.0531(19) 0.0178(15) 0.0090(14) 0.0056(15) C3 0.060(2) 0.113(4) 0.094(3) 0.060(3) 0.030(2) 0.035(2) C4 0.096(4) 0.192(6) 0.160(6) 0.114(5) 0.079(4) 0.088(4) C5 0.104(4) 0.202(6) 0.143(5) 0.111(5) 0.086(4) 0.075(4) C6 0.069(2) 0.110(3) 0.080(3) 0.054(3) 0.035(2) 0.030(2) C7 0.0423(16) 0.0541(19) 0.0436(17) 0.0094(14) 0.0088(13) 0.0013(14) C8 0.0461(17) 0.058(2) 0.0410(16) 0.0159(14) 0.0006(13) -0.0059(15) C9 0.0433(17) 0.0548(19) 0.0541(19) 0.0168(15) 0.0048(14) -0.0023(14) C10 0.0544(19) 0.0481(19) 0.066(2) 0.0059(16) 0.0223(17) -0.0091(15) C11 0.060(2) 0.054(2) 0.057(2) 0.0009(16) 0.0199(16) -0.0136(16) C12 0.084(3) 0.059(2) 0.077(3) -0.008(2) 0.020(2) -0.024(2) C13 0.098(3) 0.053(2) 0.116(4) -0.011(2) 0.039(3) -0.019(2) C14 0.093(3) 0.049(2) 0.132(4) 0.009(2) 0.043(3) 0.002(2) C15 0.062(2) 0.055(2) 0.102(3) 0.014(2) 0.020(2) -0.0011(18) C16 0.059(2) 0.069(2) 0.054(2) 0.0023(17) 0.0051(16) -0.0302(18) C17 0.0407(17) 0.080(3) 0.058(2) 0.0071(18) 0.0068(15) -0.0187(17) C18 0.0396(16) 0.0582(19) 0.0444(17) 0.0000(15) 0.0021(13) -0.0025(14) C19 0.0426(16) 0.0450(17) 0.0400(16) 0.0011(13) 0.0013(13) 0.0032(13) C20 0.0570(19) 0.0532(19) 0.0475(19) 0.0034(15) 0.0099(15) -0.0014(15) C21 0.077(3) 0.073(2) 0.047(2) -0.0044(17) 0.0152(18) -0.006(2) C22 0.074(3) 0.091(3) 0.052(2) -0.020(2) 0.0042(18) -0.018(2) C23 0.060(2) 0.075(3) 0.057(2) -0.0114(18) 0.0025(17) -0.0198(19) C24 0.0481(18) 0.0595(19) 0.0410(17) 0.0014(15) 0.0019(14) -0.0071(15) C25 0.0447(16) 0.0398(16) 0.0321(14) 0.0013(12) 0.0056(12) -0.0050(13) C26 0.0364(14) 0.0355(14) 0.0315(14) 0.0012(11) 0.0016(11) -0.0047(11) C27 0.0364(14) 0.0405(15) 0.0354(14) 0.0003(12) 0.0086(11) 0.0000(12) C28 0.0360(14) 0.0392(15) 0.0382(15) 0.0049(12) 0.0056(12) 0.0037(12) C29 0.060(2) 0.0472(19) 0.0432(18) -0.0031(15) -0.0010(15) 0.0152(16) C30 0.0532(18) 0.0451(17) 0.0402(16) -0.0025(13) -0.0004(14) 0.0124(14) C31 0.060(2) 0.0517(19) 0.0434(17) 0.0012(14) 0.0081(15) 0.0081(16) C32 0.061(2) 0.0450(18) 0.0518(19) -0.0058(15) 0.0033(16) 0.0049(15) N5 0.143(4) 0.107(3) 0.144(4) 0.023(3) 0.063(4) 0.006(3) O7 0.208(5) 0.143(4) 0.149(4) -0.009(3) 0.041(4) 0.041(4) C33 0.207(7) 0.173(7) 0.155(6) -0.006(6) 0.071(6) 0.048(6) C34 0.204(5) 0.184(5) 0.205(5) 0.011(4) 0.056(4) 0.012(4) C35 0.238(8) 0.199(7) 0.194(7) 0.038(6) 0.103(6) 0.000(6) N6 0.131(4) 0.158(5) 0.130(4) 0.010(4) 0.048(3) -0.046(4) O8 0.410(10) 0.330(9) 0.270(8) -0.065(7) 0.094(7) -0.067(8) C36 0.226(8) 0.298(10) 0.295(10) 0.081(8) 0.114(8) -0.097(7) C37 0.218(6) 0.206(6) 0.204(5) -0.012(4) 0.044(4) -0.006(4) C38 0.168(5) 0.178(5) 0.215(5) 0.021(4) 0.037(4) -0.024(4) _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 2.059(2) . ? Co1 O3 2.082(2) . ? Co1 N1 2.085(2) . ? Co1 O5 2.090(2) . ? Co1 O6 2.256(2) . ? Co1 O4 2.261(2) . ? Co1 C29 2.489(3) . ? Co1 C25 2.490(3) . ? O1 C10 1.376(4) . ? O1 C9 1.430(4) . ? O2 C11 1.367(4) . ? O2 C16 1.432(4) . ? O3 C25 1.266(3) . ? O4 C25 1.250(4) . ? O5 C29 1.252(4) . ? O6 C29 1.254(4) . ? N1 C7 1.315(4) . ? N1 C1 1.389(4) . ? N2 C7 1.344(4) . ? N2 C2 1.381(4) . ? N2 C8 1.466(4) . ? N3 C24 1.346(4) . ? N3 C18 1.387(4) . ? N3 C17 1.464(4) . ? N4 C24 1.315(4) . ? N4 C19 1.399(4) . ? C1 C6 1.379(5) . ? C1 C2 1.402(4) . ? C2 C3 1.378(5) . ? C3 C4 1.362(6) . ? C3 H3 0.9300 . ? C4 C5 1.410(7) . ? C4 H4 0.9300 . ? C5 C6 1.362(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.500(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.379(5) . ? C10 C11 1.407(5) . ? C11 C12 1.390(5) . ? C12 C13 1.390(6) . ? C12 H12 0.9300 . ? C13 C14 1.360(7) . ? C13 H13 0.9300 . ? C14 C15 1.398(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.497(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.387(5) . ? C18 C19 1.394(4) . ? C19 C20 1.391(4) . ? C20 C21 1.373(5) . ? C20 H20 0.9300 . ? C21 C22 1.399(5) . ? C21 H21 0.9300 . ? C22 C23 1.368(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.497(4) . ? C26 C28 1.383(4) . ? C26 C27 1.390(4) . ? C27 C28 1.391(4) 3_756 ? C27 H27 0.9300 . ? C28 C27 1.391(4) 3_756 ? C28 H28 0.9300 . ? C29 C30 1.501(4) . ? C30 C32 1.376(5) 3_755 ? C30 C31 1.389(5) . ? C31 C32 1.394(4) . ? C31 H31 0.9300 . ? C32 C30 1.376(5) 3_755 ? C32 H32 0.9300 . ? N5 C33 1.363(7) . ? N5 C34 1.428(7) . ? N5 C35 1.443(7) . ? O7 C33 1.208(7) . ? C33 H33 0.9300 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? N6 C38 1.382(7) . ? N6 C36 1.408(8) . ? N6 C37 1.456(7) . ? O8 C36 1.222(8) . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 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 N4 Co1 O3 107.48(10) . . ? N4 Co1 N1 94.39(10) . . ? O3 Co1 N1 104.84(9) . . ? N4 Co1 O5 149.29(11) . . ? O3 Co1 O5 97.42(10) . . ? N1 Co1 O5 96.32(10) . . ? N4 Co1 O6 91.71(10) . . ? O3 Co1 O6 155.93(10) . . ? N1 Co1 O6 87.55(10) . . ? O5 Co1 O6 60.20(10) . . ? N4 Co1 O4 91.39(9) . . ? O3 Co1 O4 60.48(8) . . ? N1 Co1 O4 165.29(9) . . ? O5 Co1 O4 85.41(9) . . ? O6 Co1 O4 105.81(8) . . ? N4 Co1 C29 121.37(12) . . ? O3 Co1 C29 127.40(11) . . ? N1 Co1 C29 90.48(10) . . ? O5 Co1 C29 30.16(11) . . ? O6 Co1 C29 30.13(10) . . ? O4 Co1 C29 98.04(9) . . ? N4 Co1 C25 102.36(9) . . ? O3 Co1 C25 30.54(9) . . ? N1 Co1 C25 135.27(10) . . ? O5 Co1 C25 89.94(9) . . ? O6 Co1 C25 132.28(10) . . ? O4 Co1 C25 30.02(8) . . ? C29 Co1 C25 114.06(11) . . ? C10 O1 C9 116.4(2) . . ? C11 O2 C16 116.7(3) . . ? C25 O3 Co1 92.80(17) . . ? C25 O4 Co1 85.16(17) . . ? C29 O5 Co1 92.8(2) . . ? C29 O6 Co1 85.3(2) . . ? C7 N1 C1 105.1(2) . . ? C7 N1 Co1 124.5(2) . . ? C1 N1 Co1 130.1(2) . . ? C7 N2 C2 106.6(2) . . ? C7 N2 C8 124.9(3) . . ? C2 N2 C8 128.5(3) . . ? C24 N3 C18 106.8(3) . . ? C24 N3 C17 125.6(3) . . ? C18 N3 C17 127.6(3) . . ? C24 N4 C19 105.1(3) . . ? C24 N4 Co1 123.5(2) . . ? C19 N4 Co1 131.1(2) . . ? C6 C1 N1 130.6(3) . . ? C6 C1 C2 120.6(3) . . ? N1 C1 C2 108.8(3) . . ? C3 C2 N2 132.2(3) . . ? C3 C2 C1 122.0(3) . . ? N2 C2 C1 105.8(3) . . ? C4 C3 C2 116.9(4) . . ? C4 C3 H3 121.5 . . ? C2 C3 H3 121.5 . . ? C3 C4 C5 121.3(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 121.8(4) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 117.4(4) . . ? C5 C6 H6 121.3 . . ? C1 C6 H6 121.3 . . ? N1 C7 N2 113.7(3) . . ? N1 C7 H7 123.2 . . ? N2 C7 H7 123.2 . . ? N2 C8 C9 113.6(3) . . ? N2 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N2 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? O1 C9 C8 108.6(2) . . ? O1 C9 H9A 110.0 . . ? C8 C9 H9A 110.0 . . ? O1 C9 H9B 110.0 . . ? C8 C9 H9B 110.0 . . ? H9A C9 H9B 108.3 . . ? O1 C10 C15 124.5(3) . . ? O1 C10 C11 115.7(3) . . ? C15 C10 C11 119.8(3) . . ? O2 C11 C12 124.3(3) . . ? O2 C11 C10 116.3(3) . . ? C12 C11 C10 119.4(4) . . ? C13 C12 C11 119.9(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 119.8(4) . . ? C10 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? O2 C16 C17 108.0(3) . . ? O2 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? O2 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? N3 C17 C16 113.5(3) . . ? N3 C17 H17A 108.9 . . ? C16 C17 H17A 108.9 . . ? N3 C17 H17B 108.9 . . ? C16 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C23 C18 N3 132.4(3) . . ? C23 C18 C19 121.9(3) . . ? N3 C18 C19 105.7(3) . . ? C20 C19 C18 120.5(3) . . ? C20 C19 N4 130.5(3) . . ? C18 C19 N4 108.9(3) . . ? C21 C20 C19 117.5(3) . . ? C21 C20 H20 121.3 . . ? C19 C20 H20 121.3 . . ? C20 C21 C22 121.4(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 121.6(3) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C18 117.0(3) . . ? C22 C23 H23 121.5 . . ? C18 C23 H23 121.5 . . ? N4 C24 N3 113.4(3) . . ? N4 C24 H24 123.3 . . ? N3 C24 H24 123.3 . . ? O4 C25 O3 121.2(3) . . ? O4 C25 C26 119.4(3) . . ? O3 C25 C26 119.4(3) . . ? O4 C25 Co1 64.82(15) . . ? O3 C25 Co1 56.66(14) . . ? C26 C25 Co1 174.6(2) . . ? C28 C26 C27 119.8(3) . . ? C28 C26 C25 120.5(3) . . ? C27 C26 C25 119.7(3) . . ? C26 C27 C28 119.9(3) . 3_756 ? C26 C27 H27 120.0 . . ? C28 C27 H27 120.0 3_756 . ? C26 C28 C27 120.3(3) . 3_756 ? C26 C28 H28 119.8 . . ? C27 C28 H28 119.8 3_756 . ? O5 C29 O6 121.3(3) . . ? O5 C29 C30 118.9(3) . . ? O6 C29 C30 119.8(3) . . ? O5 C29 Co1 57.00(17) . . ? O6 C29 Co1 64.58(17) . . ? C30 C29 Co1 172.6(2) . . ? C32 C30 C31 119.9(3) 3_755 . ? C32 C30 C29 120.6(3) 3_755 . ? C31 C30 C29 119.5(3) . . ? C30 C31 C32 119.5(3) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C30 C32 C31 120.6(3) 3_755 . ? C30 C32 H32 119.7 3_755 . ? C31 C32 H32 119.7 . . ? C33 N5 C34 123.4(5) . . ? C33 N5 C35 120.1(5) . . ? C34 N5 C35 116.3(5) . . ? O7 C33 N5 120.9(7) . . ? O7 C33 H33 119.6 . . ? N5 C33 H33 119.6 . . ? N5 C34 H34A 109.5 . . ? N5 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N5 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N5 C35 H35A 109.5 . . ? N5 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N5 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C38 N6 C36 125.0(6) . . ? C38 N6 C37 119.0(5) . . ? C36 N6 C37 115.8(5) . . ? O8 C36 N6 114.2(10) . . ? O8 C36 H36 122.9 . . ? N6 C36 H36 122.9 . . ? N6 C37 H37A 109.5 . . ? N6 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N6 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N6 C38 H38A 109.5 . . ? N6 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N6 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 N4 Co1 O3 C25 -84.71(18) . . . . ? N1 Co1 O3 C25 175.71(17) . . . . ? O5 Co1 O3 C25 77.12(18) . . . . ? O6 Co1 O3 C25 56.7(3) . . . . ? O4 Co1 O3 C25 -3.29(16) . . . . ? C29 Co1 O3 C25 73.4(2) . . . . ? N4 Co1 O4 C25 112.71(18) . . . . ? O3 Co1 O4 C25 3.34(16) . . . . ? N1 Co1 O4 C25 -0.5(5) . . . . ? O5 Co1 O4 C25 -97.87(18) . . . . ? O6 Co1 O4 C25 -155.12(17) . . . . ? C29 Co1 O4 C25 -125.33(19) . . . . ? N4 Co1 O5 C29 -29.7(3) . . . . ? O3 Co1 O5 C29 -174.09(19) . . . . ? N1 Co1 O5 C29 80.0(2) . . . . ? O6 Co1 O5 C29 -3.52(18) . . . . ? O4 Co1 O5 C29 -114.7(2) . . . . ? C25 Co1 O5 C29 -144.4(2) . . . . ? N4 Co1 O6 C29 170.49(19) . . . . ? O3 Co1 O6 C29 27.0(3) . . . . ? N1 Co1 O6 C29 -95.19(19) . . . . ? O5 Co1 O6 C29 3.52(18) . . . . ? O4 Co1 O6 C29 78.56(19) . . . . ? C25 Co1 O6 C29 62.0(2) . . . . ? N4 Co1 N1 C7 68.2(3) . . . . ? O3 Co1 N1 C7 177.6(2) . . . . ? O5 Co1 N1 C7 -83.0(3) . . . . ? O6 Co1 N1 C7 -23.3(3) . . . . ? O4 Co1 N1 C7 -179.0(3) . . . . ? C29 Co1 N1 C7 -53.3(3) . . . . ? C25 Co1 N1 C7 -179.3(2) . . . . ? N4 Co1 N1 C1 -105.7(3) . . . . ? O3 Co1 N1 C1 3.7(3) . . . . ? O5 Co1 N1 C1 103.2(3) . . . . ? O6 Co1 N1 C1 162.8(3) . . . . ? O4 Co1 N1 C1 7.2(6) . . . . ? C29 Co1 N1 C1 132.8(3) . . . . ? C25 Co1 N1 C1 6.8(3) . . . . ? O3 Co1 N4 C24 -170.1(2) . . . . ? N1 Co1 N4 C24 -63.0(3) . . . . ? O5 Co1 N4 C24 47.2(4) . . . . ? O6 Co1 N4 C24 24.7(3) . . . . ? O4 Co1 N4 C24 130.6(3) . . . . ? C29 Co1 N4 C24 30.3(3) . . . . ? C25 Co1 N4 C24 158.8(3) . . . . ? O3 Co1 N4 C19 2.4(3) . . . . ? N1 Co1 N4 C19 109.4(3) . . . . ? O5 Co1 N4 C19 -140.3(3) . . . . ? O6 Co1 N4 C19 -162.9(3) . . . . ? O4 Co1 N4 C19 -57.0(3) . . . . ? C29 Co1 N4 C19 -157.3(2) . . . . ? C25 Co1 N4 C19 -28.8(3) . . . . ? C7 N1 C1 C6 179.5(4) . . . . ? Co1 N1 C1 C6 -5.7(6) . . . . ? C7 N1 C1 C2 0.5(4) . . . . ? Co1 N1 C1 C2 175.3(2) . . . . ? C7 N2 C2 C3 -178.5(4) . . . . ? C8 N2 C2 C3 0.5(6) . . . . ? C7 N2 C2 C1 0.6(4) . . . . ? C8 N2 C2 C1 179.6(3) . . . . ? C6 C1 C2 C3 -0.6(6) . . . . ? N1 C1 C2 C3 178.5(4) . . . . ? C6 C1 C2 N2 -179.8(4) . . . . ? N1 C1 C2 N2 -0.7(4) . . . . ? N2 C2 C3 C4 178.4(5) . . . . ? C1 C2 C3 C4 -0.5(8) . . . . ? C2 C3 C4 C5 1.8(11) . . . . ? C3 C4 C5 C6 -2.0(13) . . . . ? C4 C5 C6 C1 0.7(11) . . . . ? N1 C1 C6 C5 -178.4(5) . . . . ? C2 C1 C6 C5 0.5(7) . . . . ? C1 N1 C7 N2 -0.1(4) . . . . ? Co1 N1 C7 N2 -175.3(2) . . . . ? C2 N2 C7 N1 -0.3(4) . . . . ? C8 N2 C7 N1 -179.3(3) . . . . ? C7 N2 C8 C9 -107.1(4) . . . . ? C2 N2 C8 C9 74.0(4) . . . . ? C10 O1 C9 C8 -179.6(3) . . . . ? N2 C8 C9 O1 62.1(4) . . . . ? C9 O1 C10 C15 -8.3(5) . . . . ? C9 O1 C10 C11 172.7(3) . . . . ? C16 O2 C11 C12 4.0(5) . . . . ? C16 O2 C11 C10 -177.4(3) . . . . ? O1 C10 C11 O2 0.4(4) . . . . ? C15 C10 C11 O2 -178.7(3) . . . . ? O1 C10 C11 C12 179.0(3) . . . . ? C15 C10 C11 C12 -0.1(5) . . . . ? O2 C11 C12 C13 178.8(4) . . . . ? C10 C11 C12 C13 0.3(6) . . . . ? C11 C12 C13 C14 0.3(7) . . . . ? C12 C13 C14 C15 -1.2(7) . . . . ? O1 C10 C15 C14 -179.8(4) . . . . ? C11 C10 C15 C14 -0.7(6) . . . . ? C13 C14 C15 C10 1.4(7) . . . . ? C11 O2 C16 C17 -174.1(3) . . . . ? C24 N3 C17 C16 104.6(4) . . . . ? C18 N3 C17 C16 -74.4(4) . . . . ? O2 C16 C17 N3 -65.9(4) . . . . ? C24 N3 C18 C23 -179.8(4) . . . . ? C17 N3 C18 C23 -0.7(6) . . . . ? C24 N3 C18 C19 0.6(3) . . . . ? C17 N3 C18 C19 179.7(3) . . . . ? C23 C18 C19 C20 0.9(5) . . . . ? N3 C18 C19 C20 -179.4(3) . . . . ? C23 C18 C19 N4 -179.8(3) . . . . ? N3 C18 C19 N4 -0.2(3) . . . . ? C24 N4 C19 C20 178.9(3) . . . . ? Co1 N4 C19 C20 5.4(5) . . . . ? C24 N4 C19 C18 -0.3(3) . . . . ? Co1 N4 C19 C18 -173.7(2) . . . . ? C18 C19 C20 C21 -0.9(5) . . . . ? N4 C19 C20 C21 -180.0(3) . . . . ? C19 C20 C21 C22 0.3(6) . . . . ? C20 C21 C22 C23 0.3(6) . . . . ? C21 C22 C23 C18 -0.3(6) . . . . ? N3 C18 C23 C22 -179.8(4) . . . . ? C19 C18 C23 C22 -0.3(5) . . . . ? C19 N4 C24 N3 0.7(4) . . . . ? Co1 N4 C24 N3 174.8(2) . . . . ? C18 N3 C24 N4 -0.8(4) . . . . ? C17 N3 C24 N4 -180.0(3) . . . . ? Co1 O4 C25 O3 -5.6(3) . . . . ? Co1 O4 C25 C26 176.1(2) . . . . ? Co1 O3 C25 O4 6.1(3) . . . . ? Co1 O3 C25 C26 -175.6(2) . . . . ? N4 Co1 C25 O4 -70.75(19) . . . . ? O3 Co1 C25 O4 -174.3(3) . . . . ? N1 Co1 C25 O4 179.83(16) . . . . ? O5 Co1 C25 O4 80.89(18) . . . . ? O6 Co1 C25 O4 33.2(2) . . . . ? C29 Co1 C25 O4 62.21(19) . . . . ? N4 Co1 C25 O3 103.52(18) . . . . ? N1 Co1 C25 O3 -5.9(2) . . . . ? O5 Co1 C25 O3 -104.84(18) . . . . ? O6 Co1 C25 O3 -152.56(16) . . . . ? O4 Co1 C25 O3 174.3(3) . . . . ? C29 Co1 C25 O3 -123.52(18) . . . . ? N4 Co1 C25 C26 148(2) . . . . ? O3 Co1 C25 C26 45(2) . . . . ? N1 Co1 C25 C26 39(2) . . . . ? O5 Co1 C25 C26 -60(2) . . . . ? O6 Co1 C25 C26 -108(2) . . . . ? O4 Co1 C25 C26 -141(2) . . . . ? C29 Co1 C25 C26 -79(2) . . . . ? O4 C25 C26 C28 165.2(3) . . . . ? O3 C25 C26 C28 -13.2(4) . . . . ? Co1 C25 C26 C28 -55(2) . . . . ? O4 C25 C26 C27 -13.5(4) . . . . ? O3 C25 C26 C27 168.2(3) . . . . ? Co1 C25 C26 C27 126(2) . . . . ? C28 C26 C27 C28 -0.5(4) . . . 3_756 ? C25 C26 C27 C28 178.2(2) . . . 3_756 ? C27 C26 C28 C27 0.5(4) . . . 3_756 ? C25 C26 C28 C27 -178.2(2) . . . 3_756 ? Co1 O5 C29 O6 6.4(3) . . . . ? Co1 O5 C29 C30 -172.7(2) . . . . ? Co1 O6 C29 O5 -6.0(3) . . . . ? Co1 O6 C29 C30 173.2(3) . . . . ? N4 Co1 C29 O5 162.75(19) . . . . ? O3 Co1 C29 O5 7.4(2) . . . . ? N1 Co1 C29 O5 -101.8(2) . . . . ? O6 Co1 C29 O5 173.9(3) . . . . ? O4 Co1 C29 O5 66.2(2) . . . . ? C25 Co1 C29 O5 39.6(2) . . . . ? N4 Co1 C29 O6 -11.2(2) . . . . ? O3 Co1 C29 O6 -166.52(16) . . . . ? N1 Co1 C29 O6 84.28(19) . . . . ? O5 Co1 C29 O6 -173.9(3) . . . . ? O4 Co1 C29 O6 -107.75(18) . . . . ? C25 Co1 C29 O6 -134.30(18) . . . . ? N4 Co1 C29 C30 -138.6(19) . . . . ? O3 Co1 C29 C30 66(2) . . . . ? N1 Co1 C29 C30 -43(2) . . . . ? O5 Co1 C29 C30 58.7(19) . . . . ? O6 Co1 C29 C30 -127(2) . . . . ? O4 Co1 C29 C30 125(2) . . . . ? C25 Co1 C29 C30 98(2) . . . . ? O5 C29 C30 C32 171.3(3) . . . 3_755 ? O6 C29 C30 C32 -7.9(5) . . . 3_755 ? Co1 C29 C30 C32 116.4(19) . . . 3_755 ? O5 C29 C30 C31 -7.7(4) . . . . ? O6 C29 C30 C31 173.1(3) . . . . ? Co1 C29 C30 C31 -63(2) . . . . ? C32 C30 C31 C32 -0.2(5) 3_755 . . . ? C29 C30 C31 C32 178.8(3) . . . . ? C30 C31 C32 C30 0.2(5) . . . 3_755 ? C34 N5 C33 O7 -178.0(9) . . . . ? C35 N5 C33 O7 -2.3(14) . . . . ? C38 N6 C36 O8 7.2(18) . . . . ? C37 N6 C36 O8 -178.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.432 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 941771' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_100129c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28.50 H33.50 Cu N4 O8.25' _chemical_formula_weight 627.63 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 C2/c 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' '-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 21.6962(17) _cell_length_b 16.6659(17) _cell_length_c 17.1799(15) _cell_angle_alpha 90.00 _cell_angle_beta 102.019(2) _cell_angle_gamma 90.00 _cell_volume 6075.8(9) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4038 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 22.27 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2620 _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8301 _exptl_absorpt_correction_T_max 0.8606 _exptl_absorpt_process_details sadabs _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 14826 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5324 _reflns_number_gt 3145 _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^)+(0.1009P)^2^+7.7234P] 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 5324 _refine_ls_number_parameters 395 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.1108 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.2042 _refine_ls_wR_factor_gt 0.1724 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.072 _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 0.17369(3) 0.18049(4) 0.24029(4) 0.0708(3) Uani 1 1 d U . . O1 O 0.43111(16) 0.0873(2) 0.3824(2) 0.0805(11) Uani 1 1 d . . . O2 O 0.43909(16) 0.2415(2) 0.3661(2) 0.0704(9) Uani 1 1 d . . . O3 O 0.1649(2) 0.1986(3) 0.3852(2) 0.1029(9) Uani 1 1 d U . . O4 O 0.1102(2) 0.1272(3) 0.2900(2) 0.0981(9) Uani 1 1 d U . . O5 O 0.11025(19) 0.2599(2) 0.1899(3) 0.0897(12) Uani 1 1 d . . . O6 O 0.1096(2) 0.1661(3) 0.1029(3) 0.0992(13) Uani 1 1 d . . . N1 N 0.2326(2) 0.0882(3) 0.2659(3) 0.0694(11) Uani 1 1 d . . . N2 N 0.3102(2) 0.0125(3) 0.3322(3) 0.0721(12) Uani 1 1 d . . . N3 N 0.3264(2) 0.3275(3) 0.2892(3) 0.0680(11) Uani 1 1 d . . . N4 N 0.2448(2) 0.2536(3) 0.2347(2) 0.0674(11) Uani 1 1 d . . . C1 C 0.2496(2) 0.0338(3) 0.2128(3) 0.0612(13) Uani 1 1 d . . . C2 C 0.2983(2) -0.0141(3) 0.2541(4) 0.0675(14) Uani 1 1 d . . . C3 C 0.3242(3) -0.0753(3) 0.2169(5) 0.0879(19) Uani 1 1 d . . . H3 H 0.3557 -0.1083 0.2450 0.106 Uiso 1 1 calc R . . C4 C 0.3014(3) -0.0854(4) 0.1371(5) 0.0937(19) Uani 1 1 d . . . H4 H 0.3187 -0.1249 0.1100 0.112 Uiso 1 1 calc R . . C5 C 0.2526(3) -0.0376(4) 0.0954(4) 0.0841(17) Uani 1 1 d . . . H5 H 0.2371 -0.0468 0.0414 0.101 Uiso 1 1 calc R . . C6 C 0.2273(3) 0.0229(3) 0.1332(3) 0.0693(14) Uani 1 1 d . . . H6 H 0.1957 0.0557 0.1052 0.083 Uiso 1 1 calc R . . C7 C 0.2694(3) 0.0735(4) 0.3352(4) 0.0760(15) Uani 1 1 d . . . H7 H 0.2676 0.1018 0.3814 0.091 Uiso 1 1 calc R . . C8 C 0.3589(3) -0.0145(4) 0.3988(4) 0.091(2) Uani 1 1 d . . . H8A H 0.3545 -0.0718 0.4059 0.110 Uiso 1 1 calc R . . H8B H 0.3530 0.0119 0.4471 0.110 Uiso 1 1 calc R . . C9 C 0.4245(3) 0.0030(3) 0.3866(4) 0.0902(19) Uani 1 1 d . . . H9A H 0.4556 -0.0185 0.4305 0.108 Uiso 1 1 calc R . . H9B H 0.4307 -0.0218 0.3378 0.108 Uiso 1 1 calc R . . C10 C 0.4888(2) 0.1147(3) 0.3722(3) 0.0655(13) Uani 1 1 d . . . C11 C 0.4921(2) 0.1976(3) 0.3634(3) 0.0634(13) Uani 1 1 d . . . C12 C 0.5487(3) 0.2313(4) 0.3567(4) 0.0833(17) Uani 1 1 d . . . H12 H 0.5523 0.2867 0.3529 0.100 Uiso 1 1 calc R . . C13 C 0.6009(3) 0.1824(4) 0.3557(5) 0.101(2) Uani 1 1 d . . . H13 H 0.6390 0.2053 0.3506 0.121 Uiso 1 1 calc R . . C14 C 0.5962(3) 0.1011(4) 0.3621(4) 0.0924(19) Uani 1 1 d . . . H14 H 0.6309 0.0686 0.3610 0.111 Uiso 1 1 calc R . . C15 C 0.5403(3) 0.0675(3) 0.3701(4) 0.0817(16) Uani 1 1 d . . . H15 H 0.5372 0.0121 0.3743 0.098 Uiso 1 1 calc R . . C16 C 0.4403(3) 0.3250(3) 0.3491(4) 0.0736(15) Uani 1 1 d . . . H16A H 0.4501 0.3329 0.2971 0.088 Uiso 1 1 calc R . . H16B H 0.4727 0.3511 0.3884 0.088 Uiso 1 1 calc R . . C17 C 0.3773(3) 0.3607(4) 0.3508(3) 0.0792(16) Uani 1 1 d . . . H17A H 0.3676 0.3511 0.4027 0.095 Uiso 1 1 calc R . . H17B H 0.3792 0.4183 0.3435 0.095 Uiso 1 1 calc R . . C18 C 0.3123(3) 0.3480(3) 0.2085(3) 0.0657(14) Uani 1 1 d . . . C19 C 0.2613(2) 0.3010(3) 0.1752(3) 0.0620(13) Uani 1 1 d . . . C20 C 0.2353(3) 0.3046(3) 0.0939(3) 0.0677(14) Uani 1 1 d . . . H20 H 0.2009 0.2733 0.0708 0.081 Uiso 1 1 calc R . . C21 C 0.2632(3) 0.3571(4) 0.0495(4) 0.0818(16) Uani 1 1 d . . . H21 H 0.2473 0.3608 -0.0050 0.098 Uiso 1 1 calc R . . C22 C 0.3138(3) 0.4040(4) 0.0835(4) 0.0855(17) Uani 1 1 d . . . H22 H 0.3308 0.4386 0.0510 0.103 Uiso 1 1 calc R . . C23 C 0.3407(3) 0.4018(3) 0.1640(4) 0.0746(15) Uani 1 1 d . . . H23 H 0.3749 0.4337 0.1868 0.089 Uiso 1 1 calc R . . C24 C 0.2855(3) 0.2720(4) 0.2998(3) 0.0737(15) Uani 1 1 d . . . H24 H 0.2855 0.2483 0.3488 0.088 Uiso 1 1 calc R . . C25 C 0.1210(3) 0.1524(5) 0.3610(4) 0.0999(9) Uani 1 1 d U . . C26 C 0.0799(4) 0.1209(6) 0.4131(5) 0.148(3) Uani 1 1 d . . . H26A H 0.0800 0.0633 0.4115 0.222 Uiso 1 1 calc R . . H26B H 0.0377 0.1403 0.3947 0.222 Uiso 1 1 calc R . . H26C H 0.0955 0.1387 0.4667 0.222 Uiso 1 1 calc R . . C27 C 0.0890(3) 0.2303(4) 0.1236(4) 0.0805(16) Uani 1 1 d . . . C28 C 0.0394(4) 0.2760(5) 0.0646(5) 0.132(3) Uani 1 1 d U . . H28A H 0.0585 0.3218 0.0452 0.198 Uiso 1 1 calc R . . H28B H 0.0066 0.2936 0.0905 0.198 Uiso 1 1 calc R . . H28C H 0.0218 0.2416 0.0208 0.198 Uiso 1 1 calc R . . O7 O 0.1550(5) 0.3065(6) 0.5215(5) 0.101(3) Uani 0.50 1 d PU A -1 C29 C 0.2182(6) 0.2787(7) 0.5218(6) 0.075(3) Uani 0.50 1 d PU A -1 O8 O 0.0352(7) 0.0086(5) 0.2170(7) 0.167(5) Uani 0.50 1 d PU . . O9 O 1.0000 0.3430(10) 0.2500 0.149(6) Uani 0.50 2 d SPU . . O10 O 0.0523(3) 0.0193(4) 0.0568(5) 0.194(3) Uani 1 1 d U . . H10B H 0.0384 0.0429 0.0127 0.290 Uiso 1 1 d R . . H10A H 0.0833 0.0410 0.0882 0.290 Uiso 1 1 d 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 0.0645(4) 0.0842(5) 0.0608(4) -0.0033(3) 0.0067(3) 0.0124(3) O1 0.058(2) 0.064(2) 0.118(3) 0.017(2) 0.015(2) -0.0035(17) O2 0.061(2) 0.061(2) 0.088(3) 0.0134(18) 0.0135(18) 0.0034(17) O3 0.096(2) 0.142(3) 0.0721(13) -0.0154(16) 0.0206(15) -0.0153(17) O4 0.087(2) 0.138(3) 0.0714(15) -0.0135(16) 0.0221(14) -0.0126(16) O5 0.081(3) 0.085(3) 0.090(3) -0.021(2) -0.012(2) 0.014(2) O6 0.118(4) 0.088(3) 0.085(3) -0.009(2) 0.007(3) -0.003(3) N1 0.061(3) 0.080(3) 0.067(3) 0.012(2) 0.014(2) 0.004(2) N2 0.058(3) 0.071(3) 0.083(3) 0.026(2) 0.005(2) -0.010(2) N3 0.070(3) 0.073(3) 0.058(3) -0.001(2) 0.007(2) 0.017(2) N4 0.073(3) 0.073(3) 0.054(3) -0.001(2) 0.006(2) 0.013(2) C1 0.056(3) 0.054(3) 0.073(4) 0.018(3) 0.011(3) -0.008(2) C2 0.059(3) 0.054(3) 0.092(4) 0.018(3) 0.021(3) -0.014(2) C3 0.073(4) 0.047(3) 0.143(6) 0.017(3) 0.021(4) -0.001(3) C4 0.103(5) 0.062(4) 0.116(6) -0.015(4) 0.024(4) -0.002(3) C5 0.086(4) 0.075(4) 0.092(4) 0.004(3) 0.021(3) -0.009(3) C6 0.075(3) 0.056(3) 0.079(4) 0.011(3) 0.021(3) -0.006(3) C7 0.067(3) 0.083(4) 0.078(4) 0.011(3) 0.017(3) -0.002(3) C8 0.073(4) 0.088(4) 0.103(5) 0.043(4) -0.004(3) -0.016(3) C9 0.069(4) 0.063(3) 0.130(5) 0.031(3) 0.000(4) -0.007(3) C10 0.051(3) 0.070(3) 0.074(3) 0.004(3) 0.007(2) -0.005(2) C11 0.053(3) 0.065(3) 0.072(3) 0.010(2) 0.012(2) 0.001(2) C12 0.060(3) 0.074(4) 0.116(5) 0.022(3) 0.016(3) -0.004(3) C13 0.062(4) 0.096(5) 0.148(6) 0.030(4) 0.031(4) -0.004(3) C14 0.060(4) 0.087(4) 0.134(6) 0.010(4) 0.027(4) 0.007(3) C15 0.064(3) 0.061(3) 0.120(5) 0.004(3) 0.017(3) 0.004(3) C16 0.072(4) 0.064(3) 0.079(4) 0.004(3) 0.003(3) -0.002(3) C17 0.088(4) 0.075(3) 0.068(3) -0.009(3) 0.000(3) 0.015(3) C18 0.072(3) 0.065(3) 0.059(3) -0.004(3) 0.012(3) 0.026(3) C19 0.071(3) 0.055(3) 0.060(3) -0.003(2) 0.012(3) 0.019(2) C20 0.086(4) 0.058(3) 0.060(3) -0.004(2) 0.017(3) 0.018(3) C21 0.099(5) 0.084(4) 0.061(3) -0.002(3) 0.013(3) 0.012(4) C22 0.110(5) 0.073(4) 0.076(4) 0.018(3) 0.025(4) 0.013(3) C23 0.086(4) 0.054(3) 0.086(4) 0.000(3) 0.022(3) 0.011(3) C24 0.078(4) 0.079(4) 0.063(3) 0.006(3) 0.012(3) 0.012(3) C25 0.091(2) 0.140(3) 0.0714(14) -0.0137(16) 0.0223(14) -0.0135(16) C26 0.148(8) 0.200(10) 0.113(6) 0.013(6) 0.067(6) 0.007(7) C27 0.074(4) 0.069(4) 0.089(5) 0.001(3) -0.005(3) -0.005(3) C28 0.110(6) 0.125(6) 0.134(6) 0.023(5) -0.036(5) -0.001(5) O7 0.111(7) 0.127(7) 0.067(5) 0.004(5) 0.023(5) -0.033(6) C29 0.082(7) 0.095(7) 0.051(6) 0.007(5) 0.019(5) 0.003(6) O8 0.263(14) 0.070(5) 0.128(8) -0.007(5) -0.050(8) -0.033(7) O9 0.147(12) 0.122(10) 0.192(14) 0.000 0.070(11) 0.000 O10 0.142(5) 0.142(5) 0.254(8) -0.062(5) -0.057(5) 0.012(4) _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 O5 1.975(4) . ? Cu1 O4 1.978(4) . ? Cu1 N4 1.984(5) . ? Cu1 N1 1.989(4) . ? Cu1 O3 2.553(4) . ? O1 C10 1.378(6) . ? O1 C9 1.416(6) . ? O2 C11 1.372(6) . ? O2 C16 1.423(6) . ? O3 C25 1.229(8) . ? O4 C25 1.265(7) . ? O5 C27 1.239(7) . ? O6 C27 1.240(7) . ? N1 C7 1.312(7) . ? N1 C1 1.390(7) . ? N2 C7 1.357(7) . ? N2 C2 1.385(7) . ? N2 C8 1.458(7) . ? N3 C24 1.321(7) . ? N3 C18 1.398(7) . ? N3 C17 1.469(7) . ? N4 C24 1.309(6) . ? N4 C19 1.396(6) . ? C1 C6 1.363(7) . ? C1 C2 1.395(7) . ? C2 C3 1.383(8) . ? C3 C4 1.368(9) . ? C3 H3 0.9300 . ? C4 C5 1.397(9) . ? C4 H4 0.9300 . ? C5 C6 1.374(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.508(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.373(7) . ? C10 C11 1.393(7) . ? C11 C12 1.377(7) . ? C12 C13 1.399(8) . ? C12 H12 0.9300 . ? C13 C14 1.366(8) . ? C13 H13 0.9300 . ? C14 C15 1.369(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.498(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.380(8) . ? C18 C23 1.401(8) . ? C19 C20 1.394(7) . ? C20 C21 1.380(8) . ? C20 H20 0.9300 . ? C21 C22 1.376(8) . ? C21 H21 0.9300 . ? C22 C23 1.385(8) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.483(10) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.521(8) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? O7 C29 1.445(14) . ? O10 H10B 0.8516 . ? O10 H10A 0.8502 . ? 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 O5 Cu1 O4 90.3(2) . . ? O5 Cu1 N4 92.58(18) . . ? O4 Cu1 N4 156.32(17) . . ? O5 Cu1 N1 166.42(18) . . ? O4 Cu1 N1 91.75(19) . . ? N4 Cu1 N1 90.89(17) . . ? O5 Cu1 O3 99.31(17) . . ? O4 Cu1 O3 55.36(16) . . ? N4 Cu1 O3 101.01(16) . . ? N1 Cu1 O3 92.90(17) . . ? C10 O1 C9 116.2(4) . . ? C11 O2 C16 117.5(4) . . ? C25 O3 Cu1 78.9(4) . . ? C25 O4 Cu1 105.1(4) . . ? C27 O5 Cu1 103.2(4) . . ? C7 N1 C1 106.2(5) . . ? C7 N1 Cu1 125.9(4) . . ? C1 N1 Cu1 127.3(3) . . ? C7 N2 C2 106.6(4) . . ? C7 N2 C8 125.0(6) . . ? C2 N2 C8 128.3(5) . . ? C24 N3 C18 107.1(5) . . ? C24 N3 C17 126.1(5) . . ? C18 N3 C17 126.8(5) . . ? C24 N4 C19 105.3(5) . . ? C24 N4 Cu1 119.7(4) . . ? C19 N4 Cu1 134.7(3) . . ? C6 C1 N1 131.1(5) . . ? C6 C1 C2 120.5(5) . . ? N1 C1 C2 108.5(5) . . ? C3 C2 N2 132.2(6) . . ? C3 C2 C1 121.6(6) . . ? N2 C2 C1 106.2(5) . . ? C4 C3 C2 117.2(6) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 121.4 . . ? C3 C4 C5 121.4(6) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 120.6(6) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C1 C6 C5 118.6(5) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? N1 C7 N2 112.6(5) . . ? N1 C7 H7 123.7 . . ? N2 C7 H7 123.7 . . ? N2 C8 C9 112.4(5) . . ? N2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? O1 C9 C8 107.9(5) . . ? O1 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O1 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C15 C10 O1 125.4(5) . . ? C15 C10 C11 120.3(5) . . ? O1 C10 C11 114.3(4) . . ? O2 C11 C12 123.7(5) . . ? O2 C11 C10 117.5(4) . . ? C12 C11 C10 118.7(5) . . ? C11 C12 C13 120.1(5) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 120.2(6) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.7(6) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C10 120.8(5) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O2 C16 C17 109.1(5) . . ? O2 C16 H16A 109.9 . . ? C17 C16 H16A 109.9 . . ? O2 C16 H16B 109.9 . . ? C17 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? N3 C17 C16 112.9(4) . . ? N3 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? N3 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C19 C18 N3 105.2(5) . . ? C19 C18 C23 122.8(5) . . ? N3 C18 C23 131.9(5) . . ? C18 C19 C20 120.9(5) . . ? C18 C19 N4 108.8(5) . . ? C20 C19 N4 130.3(5) . . ? C21 C20 C19 116.7(5) . . ? C21 C20 H20 121.7 . . ? C19 C20 H20 121.7 . . ? C22 C21 C20 121.9(6) . . ? C22 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? C21 C22 C23 122.8(6) . . ? C21 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C18 114.9(6) . . ? C22 C23 H23 122.6 . . ? C18 C23 H23 122.6 . . ? N4 C24 N3 113.5(5) . . ? N4 C24 H24 123.3 . . ? N3 C24 H24 123.3 . . ? O3 C25 O4 120.6(6) . . ? O3 C25 C26 122.7(7) . . ? O4 C25 C26 116.7(7) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O6 C27 O5 121.3(6) . . ? O6 C27 C28 119.2(6) . . ? O5 C27 C28 119.3(6) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? H10B O10 H10A 117.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Cu1 O3 C25 82.9(5) . . . . ? O4 Cu1 O3 C25 -1.0(5) . . . . ? N4 Cu1 O3 C25 177.4(5) . . . . ? N1 Cu1 O3 C25 -91.1(5) . . . . ? O5 Cu1 O4 C25 -100.2(5) . . . . ? N4 Cu1 O4 C25 -2.9(8) . . . . ? N1 Cu1 O4 C25 93.3(5) . . . . ? O3 Cu1 O4 C25 1.0(4) . . . . ? O4 Cu1 O5 C27 -93.4(4) . . . . ? N4 Cu1 O5 C27 110.1(4) . . . . ? N1 Cu1 O5 C27 5.4(10) . . . . ? O3 Cu1 O5 C27 -148.3(4) . . . . ? O5 Cu1 N1 C7 -178.2(7) . . . . ? O4 Cu1 N1 C7 -79.5(4) . . . . ? N4 Cu1 N1 C7 77.0(4) . . . . ? O3 Cu1 N1 C7 -24.1(4) . . . . ? O5 Cu1 N1 C1 11.7(10) . . . . ? O4 Cu1 N1 C1 110.4(4) . . . . ? N4 Cu1 N1 C1 -93.2(4) . . . . ? O3 Cu1 N1 C1 165.8(4) . . . . ? O5 Cu1 N4 C24 123.6(4) . . . . ? O4 Cu1 N4 C24 26.8(7) . . . . ? N1 Cu1 N4 C24 -69.5(4) . . . . ? O3 Cu1 N4 C24 23.6(4) . . . . ? O5 Cu1 N4 C19 -48.5(5) . . . . ? O4 Cu1 N4 C19 -145.3(5) . . . . ? N1 Cu1 N4 C19 118.3(4) . . . . ? O3 Cu1 N4 C19 -148.5(4) . . . . ? C7 N1 C1 C6 -179.4(5) . . . . ? Cu1 N1 C1 C6 -7.7(8) . . . . ? C7 N1 C1 C2 0.1(5) . . . . ? Cu1 N1 C1 C2 171.8(3) . . . . ? C7 N2 C2 C3 -178.3(5) . . . . ? C8 N2 C2 C3 5.2(8) . . . . ? C7 N2 C2 C1 0.2(5) . . . . ? C8 N2 C2 C1 -176.4(4) . . . . ? C6 C1 C2 C3 -2.0(7) . . . . ? N1 C1 C2 C3 178.5(4) . . . . ? C6 C1 C2 N2 179.4(4) . . . . ? N1 C1 C2 N2 -0.2(5) . . . . ? N2 C2 C3 C4 -179.7(5) . . . . ? C1 C2 C3 C4 2.1(8) . . . . ? C2 C3 C4 C5 -2.1(9) . . . . ? C3 C4 C5 C6 2.0(9) . . . . ? N1 C1 C6 C5 -178.8(5) . . . . ? C2 C1 C6 C5 1.8(7) . . . . ? C4 C5 C6 C1 -1.8(8) . . . . ? C1 N1 C7 N2 0.0(6) . . . . ? Cu1 N1 C7 N2 -171.8(3) . . . . ? C2 N2 C7 N1 -0.1(6) . . . . ? C8 N2 C7 N1 176.6(4) . . . . ? C7 N2 C8 C9 -112.1(6) . . . . ? C2 N2 C8 C9 63.9(7) . . . . ? C10 O1 C9 C8 179.3(5) . . . . ? N2 C8 C9 O1 63.1(7) . . . . ? C9 O1 C10 C15 -3.7(8) . . . . ? C9 O1 C10 C11 176.2(5) . . . . ? C16 O2 C11 C12 9.7(8) . . . . ? C16 O2 C11 C10 -173.8(5) . . . . ? C15 C10 C11 O2 -179.9(5) . . . . ? O1 C10 C11 O2 0.2(7) . . . . ? C15 C10 C11 C12 -3.2(8) . . . . ? O1 C10 C11 C12 176.8(5) . . . . ? O2 C11 C12 C13 178.9(6) . . . . ? C10 C11 C12 C13 2.5(9) . . . . ? C11 C12 C13 C14 -0.7(11) . . . . ? C12 C13 C14 C15 -0.5(11) . . . . ? C13 C14 C15 C10 -0.3(10) . . . . ? O1 C10 C15 C14 -177.9(6) . . . . ? C11 C10 C15 C14 2.1(9) . . . . ? C11 O2 C16 C17 176.9(4) . . . . ? C24 N3 C17 C16 100.7(6) . . . . ? C18 N3 C17 C16 -78.9(7) . . . . ? O2 C16 C17 N3 -63.3(6) . . . . ? C24 N3 C18 C19 0.2(5) . . . . ? C17 N3 C18 C19 179.8(4) . . . . ? C24 N3 C18 C23 -178.7(5) . . . . ? C17 N3 C18 C23 1.0(8) . . . . ? N3 C18 C19 C20 -178.5(4) . . . . ? C23 C18 C19 C20 0.5(7) . . . . ? N3 C18 C19 N4 0.4(5) . . . . ? C23 C18 C19 N4 179.3(4) . . . . ? C24 N4 C19 C18 -0.8(5) . . . . ? Cu1 N4 C19 C18 172.1(3) . . . . ? C24 N4 C19 C20 178.0(5) . . . . ? Cu1 N4 C19 C20 -9.1(8) . . . . ? C18 C19 C20 C21 0.0(7) . . . . ? N4 C19 C20 C21 -178.6(5) . . . . ? C19 C20 C21 C22 -0.4(8) . . . . ? C20 C21 C22 C23 0.4(9) . . . . ? C21 C22 C23 C18 0.1(8) . . . . ? C19 C18 C23 C22 -0.5(7) . . . . ? N3 C18 C23 C22 178.2(5) . . . . ? C19 N4 C24 N3 0.9(6) . . . . ? Cu1 N4 C24 N3 -173.3(3) . . . . ? C18 N3 C24 N4 -0.7(6) . . . . ? C17 N3 C24 N4 179.6(4) . . . . ? Cu1 O3 C25 O4 1.4(7) . . . . ? Cu1 O3 C25 C26 178.8(8) . . . . ? Cu1 O4 C25 O3 -1.9(9) . . . . ? Cu1 O4 C25 C26 -179.4(6) . . . . ? Cu1 O5 C27 O6 -1.6(7) . . . . ? Cu1 O5 C27 C28 -178.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.827 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 941772' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_91121b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Cl2 Co N4 O2' _chemical_formula_weight 528.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 9.7066(5) _cell_length_b 10.7611(5) _cell_length_c 13.1318(6) _cell_angle_alpha 112.4480(10) _cell_angle_beta 96.6620(10) _cell_angle_gamma 103.7680(10) _cell_volume 1198.16(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4819 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description BLOCK _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 542 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7939 _exptl_absorpt_correction_T_max 0.8684 _exptl_absorpt_process_details SADABS _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 6157 _diffrn_reflns_av_R_equivalents 0.0094 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4206 _reflns_number_gt 3824 _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^)+(0.0349P)^2^+0.5959P] 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 4206 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.07330(3) 0.74188(3) 0.26926(2) 0.03269(9) Uani 1 1 d . . . Cl1 Cl -0.03669(8) 0.80118(9) 0.41180(5) 0.0704(2) Uani 1 1 d . . . Cl2 Cl -0.02045(9) 0.51711(6) 0.14806(6) 0.0730(2) Uani 1 1 d . . . O1 O 0.39773(15) 0.81220(15) -0.01331(11) 0.0431(3) Uani 1 1 d . . . O2 O 0.58707(15) 0.81930(16) 0.14344(12) 0.0445(3) Uani 1 1 d . . . N1 N 0.08385(16) 0.85621(16) 0.17634(13) 0.0332(3) Uani 1 1 d . . . N2 N 0.16913(17) 0.92905(17) 0.05178(13) 0.0344(3) Uani 1 1 d . . . N3 N 0.52891(18) 0.8766(2) 0.36383(14) 0.0442(4) Uani 1 1 d . . . N4 N 0.28812(17) 0.79525(18) 0.33646(14) 0.0404(4) Uani 1 1 d . . . C1 C 0.08877(19) 0.9970(2) 0.20965(16) 0.0323(4) Uani 1 1 d . . . C2 C 0.14141(19) 1.0430(2) 0.13188(16) 0.0341(4) Uani 1 1 d . . . C3 C 0.1580(2) 1.1797(2) 0.14223(19) 0.0447(5) Uani 1 1 d . . . H3 H 0.1928 1.2096 0.0897 0.054 Uiso 1 1 calc R . . C4 C 0.1202(3) 1.2680(2) 0.2342(2) 0.0533(6) Uani 1 1 d . . . H4 H 0.1293 1.3601 0.2441 0.064 Uiso 1 1 calc R . . C5 C 0.0685(2) 1.2234(2) 0.31327(19) 0.0494(5) Uani 1 1 d . . . H5 H 0.0446 1.2867 0.3745 0.059 Uiso 1 1 calc R . . C6 C 0.0521(2) 1.0881(2) 0.30304(17) 0.0392(4) Uani 1 1 d . . . H6 H 0.0180 1.0589 0.3561 0.047 Uiso 1 1 calc R . . C7 C 0.1316(2) 0.8214(2) 0.08205(16) 0.0355(4) Uani 1 1 d . . . H7 H 0.1386 0.7320 0.0409 0.043 Uiso 1 1 calc R . . C8 C 0.2363(2) 0.9353(2) -0.04132(17) 0.0412(5) Uani 1 1 d . . . H8A H 0.3170 1.0221 -0.0122 0.049 Uiso 1 1 calc R . . H8B H 0.1652 0.9388 -0.0977 0.049 Uiso 1 1 calc R . . C9 C 0.2914(2) 0.8130(2) -0.09753(17) 0.0419(5) Uani 1 1 d . . . H9A H 0.2118 0.7252 -0.1297 0.050 Uiso 1 1 calc R . . H9B H 0.3348 0.8232 -0.1580 0.050 Uiso 1 1 calc R . . C10 C 0.4721(2) 0.7150(2) -0.04867(17) 0.0390(4) Uani 1 1 d . . . C11 C 0.5767(2) 0.7204(2) 0.03680(18) 0.0391(4) Uani 1 1 d . . . C12 C 0.6607(2) 0.6297(2) 0.0098(2) 0.0497(5) Uani 1 1 d . . . H12 H 0.7306 0.6329 0.0663 0.060 Uiso 1 1 calc R . . C13 C 0.6402(3) 0.5345(2) -0.1016(2) 0.0594(7) Uani 1 1 d . . . H13 H 0.6965 0.4737 -0.1198 0.071 Uiso 1 1 calc R . . C14 C 0.5383(3) 0.5294(3) -0.1844(2) 0.0614(7) Uani 1 1 d . . . H14 H 0.5259 0.4654 -0.2589 0.074 Uiso 1 1 calc R . . C15 C 0.4519(3) 0.6189(2) -0.1590(2) 0.0517(5) Uani 1 1 d . . . H15 H 0.3814 0.6138 -0.2161 0.062 Uiso 1 1 calc R . . C16 C 0.6918(2) 0.8292(3) 0.23442(19) 0.0474(5) Uani 1 1 d . . . H16A H 0.7900 0.8615 0.2256 0.057 Uiso 1 1 calc R . . H16B H 0.6767 0.7379 0.2366 0.057 Uiso 1 1 calc R . . C17 C 0.6688(2) 0.9341(3) 0.34098(19) 0.0511(6) Uani 1 1 d . . . H17A H 0.7474 0.9570 0.4043 0.061 Uiso 1 1 calc R . . H17B H 0.6706 1.0204 0.3330 0.061 Uiso 1 1 calc R . . C18 C 0.5040(2) 0.8068(2) 0.43259(17) 0.0441(5) Uani 1 1 d . . . C19 C 0.3532(2) 0.7566(2) 0.41539(17) 0.0419(5) Uani 1 1 d . . . C20 C 0.2901(3) 0.6802(3) 0.4714(2) 0.0597(6) Uani 1 1 d . . . H20 H 0.1895 0.6464 0.4603 0.072 Uiso 1 1 calc R . . C21 C 0.3841(4) 0.6569(4) 0.5445(3) 0.0824(9) Uani 1 1 d . . . H21 H 0.3459 0.6056 0.5834 0.099 Uiso 1 1 calc R . . C22 C 0.5350(3) 0.7083(4) 0.5613(3) 0.0847(10) Uani 1 1 d . . . H22 H 0.5945 0.6911 0.6119 0.102 Uiso 1 1 calc R . . C23 C 0.5987(3) 0.7832(3) 0.5060(2) 0.0635(7) Uani 1 1 d . . . H23 H 0.6994 0.8163 0.5168 0.076 Uiso 1 1 calc R . . C24 C 0.3974(2) 0.8650(2) 0.30903(18) 0.0435(5) Uani 1 1 d . . . H24 H 0.3848 0.9027 0.2568 0.052 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 0.03128(14) 0.03758(16) 0.03574(15) 0.01995(12) 0.01077(10) 0.01315(11) Cl1 0.0724(4) 0.1185(6) 0.0550(4) 0.0487(4) 0.0389(3) 0.0585(4) Cl2 0.0895(5) 0.0354(3) 0.0769(4) 0.0179(3) 0.0048(4) 0.0061(3) O1 0.0441(8) 0.0501(9) 0.0363(7) 0.0150(6) 0.0092(6) 0.0226(7) O2 0.0385(7) 0.0536(9) 0.0442(8) 0.0202(7) 0.0086(6) 0.0204(7) N1 0.0334(8) 0.0342(8) 0.0353(8) 0.0178(7) 0.0090(7) 0.0103(7) N2 0.0345(8) 0.0390(9) 0.0354(8) 0.0206(7) 0.0103(7) 0.0121(7) N3 0.0323(8) 0.0547(11) 0.0392(9) 0.0156(8) 0.0024(7) 0.0120(8) N4 0.0347(9) 0.0494(10) 0.0410(9) 0.0220(8) 0.0075(7) 0.0154(8) C1 0.0275(9) 0.0338(10) 0.0357(10) 0.0169(8) 0.0030(7) 0.0083(8) C2 0.0287(9) 0.0370(10) 0.0386(10) 0.0191(8) 0.0055(8) 0.0097(8) C3 0.0459(12) 0.0427(12) 0.0543(13) 0.0298(10) 0.0128(10) 0.0130(10) C4 0.0592(14) 0.0364(12) 0.0658(15) 0.0223(11) 0.0131(12) 0.0167(10) C5 0.0529(13) 0.0425(12) 0.0478(12) 0.0121(10) 0.0116(10) 0.0179(10) C6 0.0369(10) 0.0425(11) 0.0359(10) 0.0152(9) 0.0079(8) 0.0111(9) C7 0.0379(10) 0.0344(10) 0.0380(10) 0.0178(8) 0.0102(8) 0.0127(8) C8 0.0417(11) 0.0533(13) 0.0405(11) 0.0290(10) 0.0149(9) 0.0176(10) C9 0.0422(11) 0.0517(13) 0.0351(10) 0.0210(9) 0.0109(9) 0.0146(9) C10 0.0395(10) 0.0372(11) 0.0447(11) 0.0186(9) 0.0194(9) 0.0127(9) C11 0.0355(10) 0.0379(11) 0.0492(12) 0.0217(9) 0.0190(9) 0.0107(8) C12 0.0434(12) 0.0486(13) 0.0729(16) 0.0351(12) 0.0274(11) 0.0195(10) C13 0.0663(16) 0.0424(13) 0.0864(19) 0.0305(13) 0.0470(15) 0.0264(12) C14 0.0764(17) 0.0425(13) 0.0630(16) 0.0139(12) 0.0383(14) 0.0177(12) C15 0.0579(14) 0.0466(13) 0.0473(13) 0.0159(10) 0.0196(11) 0.0137(11) C16 0.0275(10) 0.0614(14) 0.0552(13) 0.0289(11) 0.0064(9) 0.0115(9) C17 0.0303(10) 0.0604(14) 0.0506(13) 0.0200(11) 0.0000(9) 0.0034(10) C18 0.0415(11) 0.0536(13) 0.0327(10) 0.0115(9) 0.0040(8) 0.0203(10) C19 0.0426(11) 0.0516(12) 0.0341(10) 0.0167(9) 0.0078(8) 0.0219(10) C20 0.0558(14) 0.0825(18) 0.0568(14) 0.0409(14) 0.0170(12) 0.0282(13) C21 0.083(2) 0.121(3) 0.078(2) 0.072(2) 0.0214(16) 0.042(2) C22 0.076(2) 0.132(3) 0.0722(19) 0.063(2) 0.0062(15) 0.049(2) C23 0.0515(14) 0.092(2) 0.0490(14) 0.0302(14) 0.0019(11) 0.0300(14) C24 0.0353(10) 0.0540(13) 0.0437(11) 0.0241(10) 0.0054(9) 0.0144(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N4 2.0181(16) . ? Co1 N1 2.0318(15) . ? Co1 Cl2 2.2109(7) . ? Co1 Cl1 2.2195(6) . ? O1 C10 1.377(2) . ? O1 C9 1.427(2) . ? O2 C11 1.372(2) . ? O2 C16 1.429(2) . ? N1 C7 1.323(2) . ? N1 C1 1.394(2) . ? N2 C7 1.348(2) . ? N2 C2 1.386(2) . ? N2 C8 1.467(2) . ? N3 C24 1.344(3) . ? N3 C18 1.385(3) . ? N3 C17 1.468(3) . ? N4 C24 1.317(3) . ? N4 C19 1.396(3) . ? C1 C2 1.392(3) . ? C1 C6 1.394(3) . ? C2 C3 1.392(3) . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.395(3) . ? C4 H4 0.9300 . ? C5 C6 1.378(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.499(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.379(3) . ? C10 C11 1.397(3) . ? C11 C12 1.388(3) . ? C12 C13 1.386(4) . ? C12 H12 0.9300 . ? C13 C14 1.356(4) . ? C13 H13 0.9300 . ? C14 C15 1.395(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.506(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C23 1.390(3) . ? C18 C19 1.393(3) . ? C19 C20 1.384(3) . ? C20 C21 1.381(4) . ? C20 H20 0.9300 . ? C21 C22 1.396(4) . ? C21 H21 0.9300 . ? C22 C23 1.369(4) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 H24 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 N1 99.03(7) . . ? N4 Co1 Cl2 112.73(5) . . ? N1 Co1 Cl2 106.70(5) . . ? N4 Co1 Cl1 107.51(5) . . ? N1 Co1 Cl1 117.27(5) . . ? Cl2 Co1 Cl1 112.91(3) . . ? C10 O1 C9 117.34(15) . . ? C11 O2 C16 117.58(16) . . ? C7 N1 C1 105.34(15) . . ? C7 N1 Co1 122.85(13) . . ? C1 N1 Co1 129.09(12) . . ? C7 N2 C2 106.70(15) . . ? C7 N2 C8 129.17(17) . . ? C2 N2 C8 124.00(16) . . ? C24 N3 C18 106.64(17) . . ? C24 N3 C17 125.36(19) . . ? C18 N3 C17 127.43(18) . . ? C24 N4 C19 105.10(17) . . ? C24 N4 Co1 127.34(14) . . ? C19 N4 Co1 127.38(14) . . ? C2 C1 C6 120.69(18) . . ? C2 C1 N1 108.84(16) . . ? C6 C1 N1 130.47(18) . . ? N2 C2 C3 131.62(18) . . ? N2 C2 C1 106.13(16) . . ? C3 C2 C1 122.25(19) . . ? C4 C3 C2 116.4(2) . . ? C4 C3 H3 121.8 . . ? C2 C3 H3 121.8 . . ? C3 C4 C5 121.9(2) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 121.7(2) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 117.04(19) . . ? C5 C6 H6 121.5 . . ? C1 C6 H6 121.5 . . ? N1 C7 N2 112.98(17) . . ? N1 C7 H7 123.5 . . ? N2 C7 H7 123.5 . . ? N2 C8 C9 113.99(17) . . ? N2 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N2 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.6 . . ? O1 C9 C8 107.54(16) . . ? O1 C9 H9A 110.2 . . ? C8 C9 H9A 110.2 . . ? O1 C9 H9B 110.2 . . ? C8 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? O1 C10 C15 125.1(2) . . ? O1 C10 C11 114.97(17) . . ? C15 C10 C11 120.0(2) . . ? O2 C11 C12 125.2(2) . . ? O2 C11 C10 115.12(17) . . ? C12 C11 C10 119.6(2) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.8(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C10 C15 C14 119.4(2) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? O2 C16 C17 105.95(17) . . ? O2 C16 H16A 110.5 . . ? C17 C16 H16A 110.5 . . ? O2 C16 H16B 110.5 . . ? C17 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? N3 C17 C16 110.80(18) . . ? N3 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N3 C18 C23 131.8(2) . . ? N3 C18 C19 106.01(17) . . ? C23 C18 C19 122.2(2) . . ? C20 C19 C18 121.2(2) . . ? C20 C19 N4 130.0(2) . . ? C18 C19 N4 108.80(19) . . ? C21 C20 C19 116.7(2) . . ? C21 C20 H20 121.7 . . ? C19 C20 H20 121.7 . . ? C20 C21 C22 121.5(3) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C23 C22 C21 122.4(3) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C22 C23 C18 116.0(2) . . ? C22 C23 H23 122.0 . . ? C18 C23 H23 122.0 . . ? N4 C24 N3 113.44(19) . . ? N4 C24 H24 123.3 . . ? N3 C24 H24 123.3 . . ? 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 N4 Co1 N1 C7 72.70(15) . . . . ? Cl2 Co1 N1 C7 -44.44(15) . . . . ? Cl1 Co1 N1 C7 -172.17(13) . . . . ? N4 Co1 N1 C1 -85.78(16) . . . . ? Cl2 Co1 N1 C1 157.08(14) . . . . ? Cl1 Co1 N1 C1 29.34(17) . . . . ? N1 Co1 N4 C24 -9.72(19) . . . . ? Cl2 Co1 N4 C24 102.74(18) . . . . ? Cl1 Co1 N4 C24 -132.18(18) . . . . ? N1 Co1 N4 C19 175.85(16) . . . . ? Cl2 Co1 N4 C19 -71.69(17) . . . . ? Cl1 Co1 N4 C19 53.39(17) . . . . ? C7 N1 C1 C2 -0.2(2) . . . . ? Co1 N1 C1 C2 161.17(12) . . . . ? C7 N1 C1 C6 -179.55(19) . . . . ? Co1 N1 C1 C6 -18.2(3) . . . . ? C7 N2 C2 C3 -179.2(2) . . . . ? C8 N2 C2 C3 4.6(3) . . . . ? C7 N2 C2 C1 0.8(2) . . . . ? C8 N2 C2 C1 -175.32(16) . . . . ? C6 C1 C2 N2 179.03(16) . . . . ? N1 C1 C2 N2 -0.4(2) . . . . ? C6 C1 C2 C3 -0.9(3) . . . . ? N1 C1 C2 C3 179.66(17) . . . . ? N2 C2 C3 C4 -179.6(2) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C2 C1 C6 C5 0.9(3) . . . . ? N1 C1 C6 C5 -179.86(19) . . . . ? C1 N1 C7 N2 0.8(2) . . . . ? Co1 N1 C7 N2 -162.07(12) . . . . ? C2 N2 C7 N1 -1.0(2) . . . . ? C8 N2 C7 N1 174.86(17) . . . . ? C7 N2 C8 C9 -10.7(3) . . . . ? C2 N2 C8 C9 164.51(17) . . . . ? C10 O1 C9 C8 -174.62(16) . . . . ? N2 C8 C9 O1 -59.7(2) . . . . ? C9 O1 C10 C15 0.2(3) . . . . ? C9 O1 C10 C11 178.87(17) . . . . ? C16 O2 C11 C12 -0.6(3) . . . . ? C16 O2 C11 C10 179.66(17) . . . . ? O1 C10 C11 O2 1.6(2) . . . . ? C15 C10 C11 O2 -179.68(18) . . . . ? O1 C10 C11 C12 -178.16(18) . . . . ? C15 C10 C11 C12 0.6(3) . . . . ? O2 C11 C12 C13 -179.8(2) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? O1 C10 C15 C14 177.6(2) . . . . ? C11 C10 C15 C14 -1.0(3) . . . . ? C13 C14 C15 C10 0.9(4) . . . . ? C11 O2 C16 C17 -174.49(17) . . . . ? C24 N3 C17 C16 -75.9(3) . . . . ? C18 N3 C17 C16 94.4(2) . . . . ? O2 C16 C17 N3 68.7(2) . . . . ? C24 N3 C18 C23 178.8(2) . . . . ? C17 N3 C18 C23 7.1(4) . . . . ? C24 N3 C18 C19 -0.6(2) . . . . ? C17 N3 C18 C19 -172.3(2) . . . . ? N3 C18 C19 C20 179.6(2) . . . . ? C23 C18 C19 C20 0.1(3) . . . . ? N3 C18 C19 N4 0.3(2) . . . . ? C23 C18 C19 N4 -179.2(2) . . . . ? C24 N4 C19 C20 -179.1(2) . . . . ? Co1 N4 C19 C20 -3.7(3) . . . . ? C24 N4 C19 C18 0.1(2) . . . . ? Co1 N4 C19 C18 175.52(14) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? N4 C19 C20 C21 179.2(2) . . . . ? C19 C20 C21 C22 0.3(5) . . . . ? C20 C21 C22 C23 -0.7(6) . . . . ? C21 C22 C23 C18 0.8(5) . . . . ? N3 C18 C23 C22 -179.9(3) . . . . ? C19 C18 C23 C22 -0.5(4) . . . . ? C19 N4 C24 N3 -0.5(2) . . . . ? Co1 N4 C24 N3 -175.93(14) . . . . ? C18 N3 C24 N4 0.7(3) . . . . ? C17 N3 C24 N4 172.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.521 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 941773'