# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H28 N4 O4 Zn' _chemical_formula_sum 'C37 H28 N4 O4 Zn' _chemical_formula_weight 658.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pbca _symmetry_space_group_name_Hall '-p 2ac 2ab' 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 12.0822(8) _cell_length_b 23.6760(16) _cell_length_c 29.4806(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8433.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7419 _cell_measurement_theta_min 1.38 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.037 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2720 _exptl_absorpt_coefficient_mu 0.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.867 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 45054 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7419 _reflns_number_gt 5050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0779P)^2^+10.5807P] 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 7419 _refine_ls_number_parameters 417 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.1966 _refine_ls_wR_factor_gt 0.1843 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.522 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0933(4) 0.26309(19) 0.01922(18) 0.0683(6) Uani 1 1 d U . . O4 O -0.3003(4) 0.18787(19) -0.01563(16) 0.0657(12) Uani 1 1 d . . . C37 C -0.0404(6) 0.2805(3) -0.0129(3) 0.0656(6) Uani 1 1 d U . . N2 N 0.5867(4) -0.12845(19) 0.44100(15) 0.0466(11) Uani 1 1 d . . . C33 C 0.6507(6) -0.1388(3) 0.4063(2) 0.078(2) Uani 1 1 d . . . H33 H 0.6988 -0.1694 0.4081 0.094 Uiso 1 1 calc R . . C32 C 0.5172(6) -0.0863(3) 0.4365(2) 0.071(2) Uani 1 1 d . . . H32 H 0.4697 -0.0783 0.4605 0.085 Uiso 1 1 calc R . . Zn1 Zn -0.09673(6) 0.17757(3) -0.00116(2) 0.0479(3) Uani 1 1 d U . . N1 N 0.0401(4) 0.1535(2) 0.03721(15) 0.0489(12) Uani 1 1 d . . . O3 O -0.2133(4) 0.1409(2) 0.03776(14) 0.0669(12) Uani 1 1 d . . . C28 C 0.5794(4) -0.0262(2) 0.32104(18) 0.0450(13) Uani 1 1 d . . . N4 N 0.5908(4) 0.0856(2) 0.20976(17) 0.0618(15) Uani 1 1 d . . . C34 C -0.3022(5) 0.1581(3) 0.0193(2) 0.0534(15) Uani 1 1 d . . . C29 C 0.5802(4) -0.0627(2) 0.36193(18) 0.0436(13) Uani 1 1 d . . . C7 C 0.3865(5) 0.1630(3) 0.13963(18) 0.0490(14) Uani 1 1 d . . . H7 H 0.3756 0.1996 0.1291 0.059 Uiso 1 1 calc R . . C25 C 0.5855(4) 0.0472(3) 0.24664(19) 0.0499(14) Uani 1 1 d . . . C15 C 0.8739(5) 0.1837(3) 0.1829(2) 0.0570(16) Uani 1 1 d . . . C3 C 0.2168(4) 0.1324(2) 0.09716(18) 0.0442(13) Uani 1 1 d . . . C6 C 0.3120(4) 0.1211(3) 0.12781(18) 0.0466(13) Uani 1 1 d . . . C12 C 0.6896(5) 0.1169(3) 0.20156(19) 0.0528(15) Uani 1 1 d . . . C8 C 0.4959(4) 0.0976(3) 0.18271(19) 0.0517(15) Uani 1 1 d . . . C2 C 0.2181(5) 0.1769(3) 0.06670(19) 0.0501(14) Uani 1 1 d . . . H2 H 0.2786 0.2012 0.0657 0.060 Uiso 1 1 calc R . . C1 C 0.1302(5) 0.1854(3) 0.0379(2) 0.0543(15) Uani 1 1 d . . . H1 H 0.1342 0.2155 0.0176 0.065 Uiso 1 1 calc R . . C27 C 0.6695(5) -0.0249(3) 0.2919(2) 0.0534(15) Uani 1 1 d . . . H27 H 0.7289 -0.0489 0.2972 0.064 Uiso 1 1 calc R . . C24 C 0.4940(5) 0.0454(3) 0.2746(2) 0.0565(16) Uani 1 1 d . . . H24 H 0.4338 0.0687 0.2687 0.068 Uiso 1 1 calc R . . C10 C 0.4217(5) 0.0558(3) 0.1717(2) 0.0645(18) Uani 1 1 d . . . H10 H 0.4324 0.0194 0.1827 0.077 Uiso 1 1 calc R . . C23 C 0.4913(5) 0.0092(2) 0.3112(2) 0.0530(15) Uani 1 1 d . . . H23 H 0.4290 0.0085 0.3297 0.064 Uiso 1 1 calc R . . C11 C 0.4764(5) 0.1514(3) 0.16669(18) 0.0507(14) Uani 1 1 d . . . H11 H 0.5250 0.1804 0.1743 0.061 Uiso 1 1 calc R . . C4 C 0.1226(5) 0.0992(3) 0.0967(2) 0.0621(18) Uani 1 1 d . . . H4 H 0.1164 0.0691 0.1167 0.075 Uiso 1 1 calc R . . C14 C 0.8369(5) 0.1757(3) 0.2270(2) 0.0598(16) Uani 1 1 d . . . H14 H 0.8748 0.1929 0.2507 0.072 Uiso 1 1 calc R . . C26 C 0.6729(5) 0.0113(3) 0.2553(2) 0.0579(16) Uani 1 1 d . . . H26 H 0.7345 0.0115 0.2364 0.069 Uiso 1 1 calc R . . C9 C 0.3314(5) 0.0675(3) 0.1446(2) 0.0608(17) Uani 1 1 d . . . H9 H 0.2823 0.0386 0.1375 0.073 Uiso 1 1 calc R . . C35 C -0.4102(5) 0.1417(3) 0.0410(2) 0.0654(18) Uani 1 1 d . . . H35A H -0.4095 0.1013 0.0465 0.078 Uiso 1 1 calc R . . H35B H -0.4156 0.1603 0.0702 0.078 Uiso 1 1 calc R . . C18 C 0.9722(5) 0.2188(3) 0.1725(2) 0.0639(17) Uani 1 1 d . . . C16 C 0.8184(5) 0.1561(3) 0.1489(2) 0.0680(19) Uani 1 1 d . . . H16 H 0.8425 0.1602 0.1191 0.082 Uiso 1 1 calc R . . C13 C 0.7453(5) 0.1430(3) 0.2365(2) 0.0583(16) Uani 1 1 d . . . H13 H 0.7215 0.1386 0.2663 0.070 Uiso 1 1 calc R . . C36 C -0.5112(5) 0.1561(3) 0.0137(3) 0.0684(19) Uani 1 1 d . . . H36A H -0.5738 0.1353 0.0259 0.082 Uiso 1 1 calc R . . H36B H -0.4999 0.1434 -0.0173 0.082 Uiso 1 1 calc R . . C31 C 0.5105(6) -0.0534(3) 0.3984(2) 0.073(2) Uani 1 1 d . . . H31 H 0.4586 -0.0244 0.3971 0.087 Uiso 1 1 calc R . . C5 C 0.0381(5) 0.1104(3) 0.0669(2) 0.0626(17) Uani 1 1 d . . . H5 H -0.0237 0.0870 0.0672 0.075 Uiso 1 1 calc R . . C30 C 0.6510(6) -0.1070(3) 0.3672(2) 0.079(2) Uani 1 1 d . . . H30 H 0.7002 -0.1160 0.3440 0.094 Uiso 1 1 calc R . . C17 C 0.7287(5) 0.1229(3) 0.1576(2) 0.0632(17) Uani 1 1 d . . . H17 H 0.6935 0.1042 0.1339 0.076 Uiso 1 1 calc R . . N3 N 1.1575(7) 0.2863(4) 0.1525(3) 0.109(3) Uani 1 1 d . . . C20 C 1.0743(8) 0.2800(4) 0.1239(3) 0.100(3) Uani 1 1 d . . . H20 H 1.0779 0.2990 0.0963 0.121 Uiso 1 1 calc R . . C19 C 0.9829(6) 0.2472(3) 0.1322(3) 0.081(2) Uani 1 1 d . . . H19 H 0.9277 0.2442 0.1103 0.098 Uiso 1 1 calc R . . C21 C 1.1481(7) 0.2577(4) 0.1909(3) 0.109(3) Uani 1 1 d . . . H21 H 1.2057 0.2604 0.2117 0.130 Uiso 1 1 calc R . . C22 C 1.0590(6) 0.2241(4) 0.2021(3) 0.090(2) Uani 1 1 d . . . H22 H 1.0577 0.2052 0.2297 0.108 Uiso 1 1 calc R . . O2 O -0.0109(4) 0.25097(19) -0.04231(17) 0.0728(8) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0563(11) 0.0600(9) 0.0886(11) 0.0027(10) -0.0097(10) 0.0052(10) O4 0.063(3) 0.069(3) 0.065(3) 0.011(2) 0.016(2) 0.013(2) C37 0.0552(10) 0.0604(10) 0.0811(11) 0.0025(10) -0.0123(10) 0.0064(10) N2 0.048(3) 0.046(3) 0.045(3) 0.004(2) 0.008(2) 0.007(2) C33 0.084(5) 0.090(5) 0.060(4) 0.023(4) 0.024(4) 0.048(4) C32 0.069(4) 0.083(5) 0.060(4) 0.022(4) 0.029(3) 0.027(4) Zn1 0.0473(4) 0.0555(4) 0.0409(4) -0.0015(3) -0.0105(3) 0.0061(3) N1 0.046(3) 0.055(3) 0.046(3) 0.008(2) -0.012(2) 0.001(2) O3 0.053(3) 0.090(3) 0.057(3) 0.004(2) -0.008(2) 0.003(2) C28 0.043(3) 0.052(3) 0.040(3) 0.002(2) -0.003(2) 0.001(3) N4 0.040(3) 0.091(4) 0.054(3) 0.029(3) -0.014(2) -0.011(3) C34 0.056(4) 0.055(4) 0.049(3) -0.009(3) 0.001(3) 0.004(3) C29 0.043(3) 0.048(3) 0.040(3) 0.002(2) 0.000(2) 0.003(3) C7 0.042(3) 0.063(4) 0.042(3) 0.012(3) -0.004(2) -0.002(3) C25 0.038(3) 0.066(4) 0.046(3) 0.013(3) -0.012(3) -0.004(3) C15 0.043(3) 0.076(4) 0.053(4) 0.017(3) -0.001(3) -0.005(3) C3 0.035(3) 0.055(3) 0.043(3) 0.007(3) -0.004(2) -0.001(3) C6 0.035(3) 0.064(4) 0.041(3) 0.013(3) -0.001(2) -0.004(3) C12 0.036(3) 0.076(4) 0.046(3) 0.019(3) -0.007(3) -0.001(3) C8 0.034(3) 0.075(4) 0.045(3) 0.013(3) -0.009(2) -0.004(3) C2 0.035(3) 0.061(4) 0.054(3) 0.012(3) -0.006(3) -0.006(3) C1 0.049(3) 0.060(4) 0.053(4) 0.020(3) -0.009(3) -0.003(3) C27 0.044(3) 0.063(4) 0.053(3) 0.011(3) -0.006(3) 0.007(3) C24 0.041(3) 0.069(4) 0.059(4) 0.018(3) -0.006(3) 0.005(3) C10 0.056(4) 0.067(4) 0.070(4) 0.024(3) -0.022(3) -0.003(3) C23 0.045(3) 0.064(4) 0.051(3) 0.009(3) 0.002(3) 0.006(3) C11 0.041(3) 0.067(4) 0.043(3) 0.008(3) -0.003(3) -0.012(3) C4 0.045(3) 0.071(4) 0.071(4) 0.035(3) -0.016(3) -0.012(3) C14 0.049(4) 0.083(5) 0.047(3) 0.011(3) -0.008(3) -0.006(3) C26 0.040(3) 0.082(4) 0.052(3) 0.012(3) 0.000(3) -0.005(3) C9 0.052(4) 0.065(4) 0.065(4) 0.018(3) -0.022(3) -0.013(3) C35 0.065(4) 0.065(4) 0.066(4) 0.007(3) 0.014(3) 0.003(3) C18 0.054(4) 0.077(4) 0.060(4) 0.014(3) 0.003(3) -0.002(3) C16 0.050(4) 0.112(6) 0.041(3) 0.015(4) 0.006(3) -0.006(4) C13 0.045(3) 0.086(5) 0.043(3) 0.016(3) -0.002(3) -0.006(3) C36 0.049(4) 0.058(4) 0.098(5) 0.007(4) 0.009(4) 0.004(3) C31 0.065(4) 0.083(5) 0.071(4) 0.025(4) 0.021(4) 0.033(4) C5 0.049(4) 0.065(4) 0.074(4) 0.020(3) -0.017(3) -0.011(3) C30 0.080(5) 0.104(6) 0.051(4) 0.022(4) 0.026(4) 0.045(4) C17 0.047(4) 0.098(5) 0.045(3) 0.008(3) -0.004(3) -0.007(4) N3 0.095(6) 0.130(7) 0.103(6) 0.016(5) 0.014(5) -0.039(5) C20 0.094(7) 0.120(7) 0.087(6) 0.026(5) 0.017(5) -0.021(6) C19 0.074(5) 0.103(6) 0.068(5) 0.021(4) 0.012(4) -0.015(4) C21 0.077(6) 0.146(9) 0.102(7) 0.018(6) -0.009(5) -0.037(6) C22 0.064(5) 0.116(7) 0.089(6) 0.024(5) -0.009(4) -0.021(5) O2 0.0701(14) 0.0642(14) 0.0843(14) 0.0016(13) -0.0209(13) 0.0047(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C37 1.215(8) . ? O1 Zn1 2.112(5) . ? O4 C34 1.246(8) . ? C37 O2 1.168(8) . ? C37 C36 1.544(9) 4 ? N2 C33 1.306(7) . ? N2 C32 1.312(8) . ? N2 Zn1 2.067(4) 2 ? C33 C30 1.376(9) . ? C33 H33 0.9300 . ? C32 C31 1.368(9) . ? C32 H32 0.9300 . ? Zn1 O3 2.013(4) . ? Zn1 N2 2.067(4) 2_554 ? Zn1 N1 2.082(4) . ? Zn1 O2 2.359(5) . ? N1 C1 1.327(7) . ? N1 C5 1.343(7) . ? O3 C34 1.272(7) . ? C28 C23 1.384(7) . ? C28 C27 1.387(8) . ? C28 C29 1.484(7) . ? N4 C25 1.420(7) . ? N4 C12 1.425(7) . ? N4 C8 1.426(7) . ? C34 C35 1.505(9) . ? C29 C30 1.363(8) . ? C29 C31 1.384(8) . ? C7 C11 1.375(8) . ? C7 C6 1.384(8) . ? C7 H7 0.9300 . ? C25 C26 1.379(8) . ? C25 C24 1.380(8) . ? C15 C16 1.371(9) . ? C15 C14 1.388(8) . ? C15 C18 1.481(9) . ? C3 C4 1.384(8) . ? C3 C2 1.385(7) . ? C3 C6 1.487(7) . ? C6 C9 1.382(8) . ? C12 C13 1.377(8) . ? C12 C17 1.386(8) . ? C8 C10 1.374(8) . ? C8 C11 1.378(8) . ? C2 C1 1.375(8) . ? C2 H2 0.9300 . ? C1 H1 0.9300 . ? C27 C26 1.377(8) . ? C27 H27 0.9300 . ? C24 C23 1.380(8) . ? C24 H24 0.9300 . ? C10 C9 1.381(8) . ? C10 H10 0.9300 . ? C23 H23 0.9300 . ? C11 H11 0.9300 . ? C4 C5 1.373(8) . ? C4 H4 0.9300 . ? C14 C13 1.380(8) . ? C14 H14 0.9300 . ? C26 H26 0.9300 . ? C9 H9 0.9300 . ? C35 C36 1.502(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C18 C22 1.371(10) . ? C18 C19 1.371(9) . ? C16 C17 1.364(9) . ? C16 H16 0.9300 . ? C13 H13 0.9300 . ? C36 C37 1.544(9) 4_455 ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C31 H31 0.9300 . ? C5 H5 0.9300 . ? C30 H30 0.9300 . ? C17 H17 0.9300 . ? N3 C20 1.320(11) . ? N3 C21 1.324(11) . ? C20 C19 1.372(11) . ? C20 H20 0.9300 . ? C19 H19 0.9300 . ? C21 C22 1.379(11) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C37 O1 Zn1 96.5(5) . . ? O2 C37 O1 122.4(7) . . ? O2 C37 C36 120.1(7) . 4 ? O1 C37 C36 117.4(7) . 4 ? C33 N2 C32 116.2(5) . . ? C33 N2 Zn1 120.4(4) . 2 ? C32 N2 Zn1 123.3(4) . 2 ? N2 C33 C30 123.8(6) . . ? N2 C33 H33 118.1 . . ? C30 C33 H33 118.1 . . ? N2 C32 C31 123.7(6) . . ? N2 C32 H32 118.2 . . ? C31 C32 H32 118.2 . . ? O3 Zn1 N2 105.57(19) . 2_554 ? O3 Zn1 N1 97.31(18) . . ? N2 Zn1 N1 104.32(18) 2_554 . ? O3 Zn1 O1 105.35(19) . . ? N2 Zn1 O1 140.59(19) 2_554 . ? N1 Zn1 O1 95.33(18) . . ? O3 Zn1 O2 156.63(18) . . ? N2 Zn1 O2 87.97(18) 2_554 . ? N1 Zn1 O2 97.61(17) . . ? O1 Zn1 O2 55.37(18) . . ? C1 N1 C5 116.0(5) . . ? C1 N1 Zn1 120.2(4) . . ? C5 N1 Zn1 123.2(4) . . ? C34 O3 Zn1 102.0(4) . . ? C23 C28 C27 117.4(5) . . ? C23 C28 C29 121.8(5) . . ? C27 C28 C29 120.8(5) . . ? C25 N4 C12 120.1(4) . . ? C25 N4 C8 121.3(5) . . ? C12 N4 C8 118.4(5) . . ? O4 C34 O3 121.3(6) . . ? O4 C34 C35 120.9(6) . . ? O3 C34 C35 117.8(6) . . ? C30 C29 C31 114.6(5) . . ? C30 C29 C28 123.1(5) . . ? C31 C29 C28 122.3(5) . . ? C11 C7 C6 121.1(6) . . ? C11 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C26 C25 C24 118.9(5) . . ? C26 C25 N4 120.2(5) . . ? C24 C25 N4 120.9(5) . . ? C16 C15 C14 117.6(6) . . ? C16 C15 C18 120.5(6) . . ? C14 C15 C18 121.9(6) . . ? C4 C3 C2 115.8(5) . . ? C4 C3 C6 122.7(5) . . ? C2 C3 C6 121.5(5) . . ? C9 C6 C7 117.2(5) . . ? C9 C6 C3 121.0(5) . . ? C7 C6 C3 121.8(5) . . ? C13 C12 C17 119.1(6) . . ? C13 C12 N4 121.0(5) . . ? C17 C12 N4 119.8(5) . . ? C10 C8 C11 118.3(5) . . ? C10 C8 N4 120.9(6) . . ? C11 C8 N4 120.8(5) . . ? C1 C2 C3 120.3(5) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? N1 C1 C2 124.0(5) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C26 C27 C28 121.5(5) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C23 C24 C25 120.3(5) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C8 C10 C9 120.4(6) . . ? C8 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C24 C23 C28 121.5(5) . . ? C24 C23 H23 119.3 . . ? C28 C23 H23 119.3 . . ? C7 C11 C8 121.2(6) . . ? C7 C11 H11 119.4 . . ? C8 C11 H11 119.4 . . ? C5 C4 C3 120.6(5) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C13 C14 C15 121.7(6) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C27 C26 C25 120.4(6) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C10 C9 C6 121.7(6) . . ? C10 C9 H9 119.1 . . ? C6 C9 H9 119.1 . . ? C36 C35 C34 114.7(6) . . ? C36 C35 H35A 108.6 . . ? C34 C35 H35A 108.6 . . ? C36 C35 H35B 108.6 . . ? C34 C35 H35B 108.6 . . ? H35A C35 H35B 107.6 . . ? C22 C18 C19 115.8(7) . . ? C22 C18 C15 122.2(6) . . ? C19 C18 C15 122.0(6) . . ? C17 C16 C15 121.7(6) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C12 C13 C14 119.4(6) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C35 C36 C37 114.4(6) . 4_455 ? C35 C36 H36A 108.7 . . ? C37 C36 H36A 108.7 4_455 . ? C35 C36 H36B 108.7 . . ? C37 C36 H36B 108.7 4_455 . ? H36A C36 H36B 107.6 . . ? C32 C31 C29 120.7(6) . . ? C32 C31 H31 119.6 . . ? C29 C31 H31 119.6 . . ? N1 C5 C4 123.4(6) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C29 C30 C33 121.0(6) . . ? C29 C30 H30 119.5 . . ? C33 C30 H30 119.5 . . ? C16 C17 C12 120.4(6) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? C20 N3 C21 115.0(8) . . ? N3 C20 C19 124.3(8) . . ? N3 C20 H20 117.8 . . ? C19 C20 H20 117.8 . . ? C18 C19 C20 120.5(8) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? N3 C21 C22 124.5(9) . . ? N3 C21 H21 117.7 . . ? C22 C21 H21 117.7 . . ? C18 C22 C21 119.9(8) . . ? C18 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C37 O2 Zn1 85.7(5) . . ? 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 _platon_squeeze_void_content 1 -0.027 0.500 0.004 1579 408 ' ' 2 -0.273 1.000 0.177 1579 408 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.115 _refine_diff_density_min -2.010 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 957212' ####################################################################### # # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H26 Cd N4 O4' _chemical_formula_sum 'C37 H26 Cd N4 O4' _chemical_formula_weight 703.02 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-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 13.7490(12) _cell_length_b 17.0006(15) _cell_length_c 13.1650(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.1090(10) _cell_angle_gamma 90.00 _cell_volume 3072.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3830 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.759 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_T_max 0.840 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10956 _diffrn_reflns_av_R_equivalents 0.1049 _diffrn_reflns_av_sigmaI/netI 0.0770 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3830 _reflns_number_gt 3095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0403P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3830 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2947(2) 1.19771(16) 0.3661(3) 0.0565(8) Uani 1 1 d . . . H1 H 0.2718 1.2313 0.3144 0.068 Uiso 1 1 calc R . . C2 C 0.2279(2) 1.16228(18) 0.4254(2) 0.0565(7) Uani 1 1 d . . . H2 H 0.1617 1.1718 0.4125 0.068 Uiso 1 1 calc R . . C3 C 0.2582(2) 1.11303(17) 0.5033(2) 0.0521(7) Uani 1 1 d . . . C4 C 0.3576(2) 1.1039(2) 0.5190(3) 0.0723(10) Uani 1 1 d . . . H4 H 0.3825 1.0724 0.5720 0.087 Uiso 1 1 calc R . . C5 C 0.4209(2) 1.1416(2) 0.4559(3) 0.0697(9) Uani 1 1 d . . . H5 H 0.4876 1.1350 0.4686 0.084 Uiso 1 1 calc R . . C6 C 0.1909(2) 1.06994(18) 0.5672(2) 0.0523(7) Uani 1 1 d . . . C7 C 0.0965(2) 1.09637(18) 0.5805(3) 0.0583(8) Uani 1 1 d . . . H7 H 0.0755 1.1432 0.5499 0.070 Uiso 1 1 calc R . . C8 C 0.0335(2) 1.05440(18) 0.6381(3) 0.0585(8) Uani 1 1 d . . . H8 H -0.0302 1.0716 0.6429 0.070 Uiso 1 1 calc R . . C9 C 0.0645(2) 0.98716(17) 0.6886(3) 0.0526(7) Uani 1 1 d . . . C10 C 0.1590(2) 0.96071(19) 0.6781(3) 0.0620(9) Uani 1 1 d . . . H10 H 0.1812 0.9158 0.7124 0.074 Uiso 1 1 calc R . . C11 C 0.2200(2) 1.00137(18) 0.6166(3) 0.0633(9) Uani 1 1 d . . . H11 H 0.2823 0.9821 0.6082 0.076 Uiso 1 1 calc R . . C12 C 0.0000 0.8616(2) 0.7500 0.0514(10) Uani 1 2 d S . . C13 C -0.0343(2) 0.81934(18) 0.8318(3) 0.0574(8) Uani 1 1 d . . . H13 H -0.0556 0.8459 0.8881 0.069 Uiso 1 1 calc R . . C14 C -0.0365(2) 0.73862(19) 0.8291(3) 0.0605(8) Uani 1 1 d . . . H14 H -0.0634 0.7115 0.8821 0.073 Uiso 1 1 calc R . . C15 C 0.0000 0.6965(2) 0.7500 0.0547(11) Uani 1 2 d S . . C16 C 0.0000 0.6089(2) 0.7500 0.0553(10) Uani 1 2 d S . . C17 C -0.0776(2) 0.56659(19) 0.7824(3) 0.0648(9) Uani 1 1 d . . . H17 H -0.1311 0.5925 0.8069 0.078 Uiso 1 1 calc R . . C18 C -0.0759(2) 0.48538(19) 0.7785(3) 0.0639(9) Uani 1 1 d . . . H18 H -0.1308 0.4581 0.7969 0.077 Uiso 1 1 calc R . . C19 C 0.64902(19) 1.2409(2) 0.3921(2) 0.0502(7) Uani 1 1 d . . . C20 C 0.7230(2) 1.27219(18) 0.4692(2) 0.0512(7) Uani 1 1 d . . . H20 H 0.7311 1.3264 0.4737 0.061 Uiso 1 1 calc R . . Cd1 Cd 0.5000 1.203021(16) 0.2500 0.04453(12) Uani 1 2 d S . . N1 N 0.0000 0.9444(2) 0.7500 0.0573(10) Uani 1 2 d S . . N2 N 0.39033(19) 1.18651(15) 0.3786(2) 0.0544(6) Uani 1 1 d . . . N3 N 0.0000 0.4443(2) 0.7500 0.0561(9) Uani 1 2 d S . . O1 O 0.60104(18) 1.29039(14) 0.3391(2) 0.0720(7) Uani 1 1 d . . . O2 O 0.63742(16) 1.16899(15) 0.38143(19) 0.0700(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0656(19) 0.0456(18) 0.059(2) 0.0023(13) 0.0138(16) 0.0062(14) C2 0.0556(17) 0.0460(18) 0.069(2) 0.0013(15) 0.0165(15) 0.0048(13) C3 0.0536(16) 0.0432(16) 0.0605(18) -0.0001(14) 0.0120(14) -0.0049(13) C4 0.0588(19) 0.091(3) 0.067(2) 0.0260(19) 0.0036(17) -0.0122(17) C5 0.0534(18) 0.086(3) 0.070(2) 0.0145(19) 0.0067(16) -0.0134(16) C6 0.0496(16) 0.0452(17) 0.0630(19) 0.0020(13) 0.0110(14) -0.0037(12) C7 0.0640(19) 0.0443(17) 0.069(2) 0.0112(14) 0.0205(16) 0.0095(13) C8 0.0529(17) 0.0473(18) 0.078(2) 0.0035(15) 0.0243(15) 0.0093(13) C9 0.0512(16) 0.0337(15) 0.075(2) 0.0002(13) 0.0221(15) -0.0008(12) C10 0.0506(17) 0.0469(18) 0.089(2) 0.0173(16) 0.0142(16) 0.0019(13) C11 0.0433(16) 0.057(2) 0.091(2) 0.0148(17) 0.0166(16) 0.0017(13) C12 0.045(2) 0.035(2) 0.076(3) 0.000 0.018(2) 0.000 C13 0.0627(19) 0.0415(16) 0.070(2) -0.0023(14) 0.0258(16) 0.0027(13) C14 0.066(2) 0.0439(18) 0.074(2) 0.0086(15) 0.0274(17) 0.0023(14) C15 0.053(2) 0.041(2) 0.072(3) 0.000 0.014(2) 0.000 C16 0.056(2) 0.040(2) 0.071(3) 0.000 0.008(2) 0.000 C17 0.0578(18) 0.0462(19) 0.092(3) 0.0079(17) 0.0187(17) 0.0050(14) C18 0.0572(18) 0.0466(19) 0.088(2) 0.0136(16) 0.0100(17) 0.0005(14) C19 0.0387(14) 0.0597(19) 0.0528(17) -0.0104(14) 0.0068(13) 0.0032(13) C20 0.0427(15) 0.0499(17) 0.062(2) -0.0081(13) 0.0076(14) -0.0017(11) Cd1 0.04445(18) 0.04301(19) 0.04645(19) 0.000 0.00542(12) 0.000 N1 0.055(2) 0.0353(19) 0.085(3) 0.000 0.0297(19) 0.000 N2 0.0581(15) 0.0506(15) 0.0554(16) 0.0026(11) 0.0118(12) -0.0072(11) N3 0.054(2) 0.044(2) 0.069(2) 0.000 -0.0033(18) 0.000 O1 0.0684(15) 0.0646(16) 0.0802(17) -0.0093(12) -0.0217(13) 0.0143(11) O2 0.0629(14) 0.0560(15) 0.0890(17) -0.0067(13) -0.0147(12) -0.0070(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.329(4) . ? C1 C2 1.377(4) . ? C1 H1 0.9300 . ? C2 C3 1.371(4) . ? C2 H2 0.9300 . ? C3 C4 1.381(4) . ? C3 C6 1.478(4) . ? C4 C5 1.392(4) . ? C4 H4 0.9300 . ? C5 N2 1.321(4) . ? C5 H5 0.9300 . ? C6 C11 1.384(4) . ? C6 C7 1.393(4) . ? C7 C8 1.380(4) . ? C7 H7 0.9300 . ? C8 C9 1.378(4) . ? C8 H8 0.9300 . ? C9 C10 1.389(4) . ? C9 N1 1.430(3) . ? C10 C11 1.382(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.397(4) . ? C12 C13 1.397(4) 2_556 ? C12 N1 1.409(5) . ? C13 C14 1.373(4) . ? C13 H13 0.9300 . ? C14 C15 1.380(4) . ? C14 H14 0.9300 . ? C15 C14 1.380(4) 2_556 ? C15 C16 1.489(5) . ? C16 C17 1.374(4) 2_556 ? C16 C17 1.374(4) . ? C17 C18 1.382(4) . ? C17 H17 0.9300 . ? C18 N3 1.326(4) . ? C18 H18 0.9300 . ? C19 O2 1.241(4) . ? C19 O1 1.256(4) . ? C19 C20 1.495(4) . ? C20 C20 1.309(6) 7_676 ? C20 H20 0.9300 . ? Cd1 O1 2.310(2) . ? Cd1 O1 2.310(2) 2_655 ? Cd1 N2 2.345(3) . ? Cd1 N2 2.345(3) 2_655 ? Cd1 N3 2.505(4) 7_566 ? Cd1 O2 2.558(2) . ? Cd1 O2 2.558(2) 2_655 ? N1 C9 1.430(3) 2_556 ? N3 C18 1.326(4) 2_556 ? N3 Cd1 2.505(4) 7_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C2 123.5(3) . . ? N2 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 116.0(3) . . ? C2 C3 C6 123.6(3) . . ? C4 C3 C6 120.3(3) . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N2 C5 C4 122.8(3) . . ? N2 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? C11 C6 C7 117.4(3) . . ? C11 C6 C3 120.7(3) . . ? C7 C6 C3 121.8(3) . . ? C8 C7 C6 121.2(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.1(3) . . ? C8 C9 N1 120.6(2) . . ? C10 C9 N1 120.2(3) . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C6 121.8(3) . . ? C10 C11 H11 119.1 . . ? C6 C11 H11 119.1 . . ? C13 C12 C13 118.1(4) . 2_556 ? C13 C12 N1 120.93(19) . . ? C13 C12 N1 120.93(19) 2_556 . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 122.0(3) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C14 117.5(4) 2_556 . ? C14 C15 C16 121.25(19) 2_556 . ? C14 C15 C16 121.25(19) . . ? C17 C16 C17 116.8(4) 2_556 . ? C17 C16 C15 121.6(2) 2_556 . ? C17 C16 C15 121.6(2) . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? N3 C18 C17 123.5(3) . . ? N3 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? O2 C19 O1 122.5(3) . . ? O2 C19 C20 120.4(3) . . ? O1 C19 C20 117.2(3) . . ? C20 C20 C19 123.9(4) 7_676 . ? C20 C20 H20 118.0 7_676 . ? C19 C20 H20 118.0 . . ? O1 Cd1 O1 99.97(12) . 2_655 ? O1 Cd1 N2 95.89(10) . . ? O1 Cd1 N2 92.94(10) 2_655 . ? O1 Cd1 N2 92.94(10) . 2_655 ? O1 Cd1 N2 95.89(10) 2_655 2_655 ? N2 Cd1 N2 166.25(12) . 2_655 ? O1 Cd1 N3 130.01(6) . 7_566 ? O1 Cd1 N3 130.01(6) 2_655 7_566 ? N2 Cd1 N3 83.13(6) . 7_566 ? N2 Cd1 N3 83.13(6) 2_655 7_566 ? O1 Cd1 O2 53.13(8) . . ? O1 Cd1 O2 152.97(9) 2_655 . ? N2 Cd1 O2 87.98(9) . . ? N2 Cd1 O2 88.92(9) 2_655 . ? N3 Cd1 O2 76.93(6) 7_566 . ? O1 Cd1 O2 152.97(9) . 2_655 ? O1 Cd1 O2 53.13(8) 2_655 2_655 ? N2 Cd1 O2 88.92(9) . 2_655 ? N2 Cd1 O2 87.98(9) 2_655 2_655 ? N3 Cd1 O2 76.93(6) 7_566 2_655 ? O2 Cd1 O2 153.86(11) . 2_655 ? C12 N1 C9 120.53(16) . 2_556 ? C12 N1 C9 120.53(16) . . ? C9 N1 C9 118.9(3) 2_556 . ? C5 N2 C1 116.7(3) . . ? C5 N2 Cd1 115.7(2) . . ? C1 N2 Cd1 124.3(2) . . ? C18 N3 C18 116.5(4) 2_556 . ? C18 N3 Cd1 121.8(2) 2_556 7_566 ? C18 N3 Cd1 121.8(2) . 7_566 ? C19 O1 Cd1 97.7(2) . . ? C19 O2 Cd1 86.50(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C1 C2 C3 0.8(5) . . . . ? C1 C2 C3 C4 1.8(5) . . . . ? C1 C2 C3 C6 -177.0(3) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? C6 C3 C4 C5 177.0(3) . . . . ? C3 C4 C5 N2 -0.7(6) . . . . ? C2 C3 C6 C11 155.6(3) . . . . ? C4 C3 C6 C11 -23.2(5) . . . . ? C2 C3 C6 C7 -24.7(5) . . . . ? C4 C3 C6 C7 156.6(3) . . . . ? C11 C6 C7 C8 -2.0(5) . . . . ? C3 C6 C7 C8 178.2(3) . . . . ? C6 C7 C8 C9 3.5(5) . . . . ? C7 C8 C9 C10 -2.1(5) . . . . ? C7 C8 C9 N1 178.7(3) . . . . ? C8 C9 C10 C11 -0.8(5) . . . . ? N1 C9 C10 C11 178.4(3) . . . . ? C9 C10 C11 C6 2.3(5) . . . . ? C7 C6 C11 C10 -0.9(5) . . . . ? C3 C6 C11 C10 178.9(3) . . . . ? C13 C12 C13 C14 -2.0(2) 2_556 . . . ? N1 C12 C13 C14 178.0(2) . . . . ? C12 C13 C14 C15 4.1(5) . . . . ? C13 C14 C15 C14 -2.1(2) . . . 2_556 ? C13 C14 C15 C16 177.9(2) . . . . ? C14 C15 C16 C17 40.4(2) 2_556 . . 2_556 ? C14 C15 C16 C17 -139.6(2) . . . 2_556 ? C14 C15 C16 C17 -139.6(2) 2_556 . . . ? C14 C15 C16 C17 40.4(2) . . . . ? C17 C16 C17 C18 -1.8(3) 2_556 . . . ? C15 C16 C17 C18 178.2(3) . . . . ? C16 C17 C18 N3 3.9(5) . . . . ? O2 C19 C20 C20 -1.9(5) . . . 7_676 ? O1 C19 C20 C20 178.8(4) . . . 7_676 ? C13 C12 N1 C9 -22.8(2) . . . 2_556 ? C13 C12 N1 C9 157.2(2) 2_556 . . 2_556 ? C13 C12 N1 C9 157.2(2) . . . . ? C13 C12 N1 C9 -22.8(2) 2_556 . . . ? C8 C9 N1 C12 140.4(2) . . . . ? C10 C9 N1 C12 -38.8(4) . . . . ? C8 C9 N1 C9 -39.6(2) . . . 2_556 ? C10 C9 N1 C9 141.2(4) . . . 2_556 ? C4 C5 N2 C1 3.2(5) . . . . ? C4 C5 N2 Cd1 -157.3(3) . . . . ? C2 C1 N2 C5 -3.3(5) . . . . ? C2 C1 N2 Cd1 155.4(2) . . . . ? O1 Cd1 N2 C5 -75.7(3) . . . . ? O1 Cd1 N2 C5 -176.0(2) 2_655 . . . ? N2 Cd1 N2 C5 54.0(2) 2_655 . . . ? N3 Cd1 N2 C5 54.0(2) 7_566 . . . ? O2 Cd1 N2 C5 -23.0(2) . . . . ? O2 Cd1 N2 C5 131.0(2) 2_655 . . . ? O1 Cd1 N2 C1 125.4(2) . . . . ? O1 Cd1 N2 C1 25.1(2) 2_655 . . . ? N2 Cd1 N2 C1 -104.9(2) 2_655 . . . ? N3 Cd1 N2 C1 -104.9(2) 7_566 . . . ? O2 Cd1 N2 C1 178.1(2) . . . . ? O2 Cd1 N2 C1 -27.9(2) 2_655 . . . ? C17 C18 N3 C18 -2.0(3) . . . 2_556 ? C17 C18 N3 Cd1 178.0(3) . . . 7_566 ? O2 C19 O1 Cd1 4.1(3) . . . . ? C20 C19 O1 Cd1 -176.6(2) . . . . ? O1 Cd1 O1 C19 175.0(2) 2_655 . . . ? N2 Cd1 O1 C19 80.9(2) . . . . ? N2 Cd1 O1 C19 -88.5(2) 2_655 . . . ? N3 Cd1 O1 C19 -5.0(2) 7_566 . . . ? O2 Cd1 O1 C19 -2.10(16) . . . . ? O2 Cd1 O1 C19 -179.85(16) 2_655 . . . ? O1 C19 O2 Cd1 -3.7(3) . . . . ? C20 C19 O2 Cd1 177.0(2) . . . . ? O1 Cd1 O2 C19 2.11(16) . . . . ? O1 Cd1 O2 C19 -4.3(3) 2_655 . . . ? N2 Cd1 O2 C19 -96.80(16) . . . . ? N2 Cd1 O2 C19 96.60(16) 2_655 . . . ? N3 Cd1 O2 C19 179.79(16) 7_566 . . . ? O2 Cd1 O2 C19 179.79(16) 2_655 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.383 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 957213' ####################################################################### # # 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_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C47 H32 Cd N4 O5' _chemical_formula_sum 'C47 H32 Cd N4 O5' _chemical_formula_weight 845.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/c' _symmetry_space_group_name_Hall '-p 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.9824(13) _cell_length_b 32.547(4) _cell_length_c 10.7535(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.598(2) _cell_angle_gamma 90.00 _cell_volume 4146.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7274 _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.577 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8459 _exptl_absorpt_correction_T_max 0.8836 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 7274 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7274 _reflns_number_gt 6228 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0849P)^2^+9.3153P] 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 7274 _refine_ls_number_parameters 514 _refine_ls_number_restraints 1495 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1797 _refine_ls_wR_factor_gt 0.1736 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.149 _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 O3 O 0.9945(4) 0.07170(17) 0.9221(5) 0.0848(13) Uani 1 1 d U . . C34 C 0.9527(6) 0.0999(3) 0.8503(6) 0.0798(16) Uani 1 1 d U . . C1 C 0.3245(5) 0.14395(17) -0.1471(5) 0.0582(12) Uani 1 1 d U . . H1 H 0.2552 0.1517 -0.1918 0.070 Uiso 1 1 calc R . . C2 C 0.4334(5) 0.09748(19) -0.0258(6) 0.0604(11) Uani 1 1 d U . . H2 H 0.4407 0.0723 0.0158 0.072 Uiso 1 1 calc R . . C3 C 0.5269(4) 0.12177(17) -0.0204(5) 0.0557(11) Uani 1 1 d U . . H3 H 0.5955 0.1129 0.0231 0.067 Uiso 1 1 calc R . . C4 C 0.5198(4) 0.15973(16) -0.0799(5) 0.0501(10) Uani 1 1 d U . . C5 C 0.4139(5) 0.17005(17) -0.1453(5) 0.0565(11) Uani 1 1 d U . . H5 H 0.4042 0.1949 -0.1881 0.068 Uiso 1 1 calc R . . C6 C 0.6180(4) 0.18691(16) -0.0742(5) 0.0508(10) Uani 1 1 d U . . C11 C 0.6311(5) 0.21392(17) -0.1697(5) 0.0608(12) Uani 1 1 d U . . H11 H 0.5750 0.2155 -0.2394 0.073 Uiso 1 1 calc R . . C10 C 0.7253(5) 0.23860(17) -0.1647(5) 0.0598(12) Uani 1 1 d U . . H10 H 0.7324 0.2561 -0.2314 0.072 Uiso 1 1 calc R . . C9 C 0.8092(4) 0.23752(15) -0.0615(5) 0.0491(10) Uani 1 1 d U . . C8 C 0.7983(4) 0.21049(18) 0.0341(5) 0.0548(11) Uani 1 1 d U . . H8 H 0.8547 0.2090 0.1035 0.066 Uiso 1 1 calc R . . C7 C 0.7050(4) 0.18553(18) 0.0283(5) 0.0563(11) Uani 1 1 d U . . H7 H 0.6996 0.1674 0.0939 0.068 Uiso 1 1 calc R . . C23 C 1.0073(4) 0.25179(15) 0.0216(5) 0.0477(10) Uani 1 1 d U . . C28 C 1.0580(5) 0.27714(16) 0.1167(5) 0.0541(11) Uani 1 1 d U . . H28 H 1.0273 0.3028 0.1284 0.065 Uiso 1 1 calc R . . C27 C 1.1543(4) 0.26450(16) 0.1945(5) 0.0525(11) Uani 1 1 d U . . H27 H 1.1877 0.2820 0.2576 0.063 Uiso 1 1 calc R . . C26 C 1.2021(4) 0.22628(16) 0.1806(5) 0.0466(10) Uani 1 1 d U . . C25 C 1.1499(4) 0.20121(15) 0.0841(5) 0.0463(10) Uani 1 1 d U . . H25 H 1.1802 0.1754 0.0724 0.056 Uiso 1 1 calc R . . C24 C 1.0536(4) 0.21383(15) 0.0052(5) 0.0463(10) Uani 1 1 d U . . H24 H 1.0203 0.1966 -0.0589 0.056 Uiso 1 1 calc R . . C30 C 1.3219(5) 0.2234(2) 0.3917(6) 0.0695(13) Uani 1 1 d U . . H30 H 1.2683 0.2388 0.4254 0.083 Uiso 1 1 calc R . . C29 C 1.3043(4) 0.21276(17) 0.2664(5) 0.0540(11) Uani 1 1 d U . . C33 C 1.3871(5) 0.1897(2) 0.2233(7) 0.0706(13) Uani 1 1 d U . . H33 H 1.3799 0.1820 0.1391 0.085 Uiso 1 1 calc R . . C32 C 1.4817(6) 0.1779(2) 0.3072(8) 0.0855(16) Uani 1 1 d U . . H32 H 1.5356 0.1618 0.2766 0.103 Uiso 1 1 calc R . . C12 C 0.8910(4) 0.30447(15) -0.1013(5) 0.0482(10) Uani 1 1 d U . . C13 C 0.7959(4) 0.32756(15) -0.0879(5) 0.0525(10) Uani 1 1 d U . . H13 H 0.7404 0.3164 -0.0461 0.063 Uiso 1 1 calc R . . C14 C 0.7833(4) 0.36675(15) -0.1361(5) 0.0522(11) Uani 1 1 d U . . H14 H 0.7193 0.3818 -0.1261 0.063 Uiso 1 1 calc R . . C15 C 0.8644(4) 0.38424(15) -0.1993(5) 0.0470(10) Uani 1 1 d U . . C16 C 0.9603(4) 0.36110(16) -0.2122(5) 0.0524(11) Uani 1 1 d U . . H16 H 1.0156 0.3721 -0.2546 0.063 Uiso 1 1 calc R . . C17 C 0.9733(4) 0.32190(16) -0.1624(5) 0.0525(11) Uani 1 1 d U . . H17 H 1.0382 0.3070 -0.1701 0.063 Uiso 1 1 calc R . . C18 C 0.8507(4) 0.42631(14) -0.2536(5) 0.0462(10) Uani 1 1 d U . . C19 C 0.7483(5) 0.44655(18) -0.2707(6) 0.0642(12) Uani 1 1 d U . . H19 H 0.6841 0.4336 -0.2508 0.077 Uiso 1 1 calc R . . C22 C 0.9402(5) 0.44709(17) -0.2900(6) 0.0570(11) Uani 1 1 d U . . H22 H 1.0107 0.4346 -0.2824 0.068 Uiso 1 1 calc R . . C21 C 0.9260(5) 0.48662(17) -0.3381(6) 0.0572(12) Uani 1 1 d U . . H21 H 0.9881 0.4999 -0.3618 0.069 Uiso 1 1 calc R . . C35 C 0.2694(5) 0.0696(2) 0.1881(6) 0.0693(13) Uani 1 1 d U . . C36 C 0.3307(5) 0.0732(3) 0.3190(6) 0.0793(15) Uani 1 1 d U . . C41 C 0.2877(6) 0.0982(3) 0.4055(7) 0.0935(16) Uani 1 1 d U . . H41 H 0.2210 0.1127 0.3809 0.112 Uiso 1 1 calc R . . C40 C 0.3423(6) 0.1019(3) 0.5261(7) 0.1027(17) Uani 1 1 d U . . H40 H 0.3147 0.1192 0.5833 0.123 Uiso 1 1 calc R . . C38 C 0.4891(7) 0.0570(3) 0.4762(7) 0.1025(17) Uani 1 1 d U . . H38 H 0.5594 0.0448 0.4987 0.123 Uiso 1 1 calc R . . C37 C 0.4319(6) 0.0532(3) 0.3549(7) 0.0898(15) Uani 1 1 d U . . H37 H 0.4621 0.0369 0.2971 0.108 Uiso 1 1 calc R . . C20 C 0.7415(5) 0.48642(19) -0.3178(7) 0.0689(14) Uani 1 1 d U . . H20 H 0.6723 0.4998 -0.3259 0.083 Uiso 1 1 calc R . . C31 C 1.4197(6) 0.2111(2) 0.4671(7) 0.0844(16) Uani 1 1 d U . . H31 H 1.4303 0.2194 0.5508 0.101 Uiso 1 1 calc R . . C39 C 0.4416(7) 0.0789(3) 0.5611(8) 0.1046(17) Uani 1 1 d U . . C46 C 0.6560(7) 0.1155(3) 0.6777(7) 0.1009(17) Uani 1 1 d U . . H46 H 0.6161 0.1332 0.6194 0.121 Uiso 1 1 calc R . . C45 C 0.7728(7) 0.1226(3) 0.7202(7) 0.0957(17) Uani 1 1 d U . . H45 H 0.8097 0.1448 0.6904 0.115 Uiso 1 1 calc R . . C44 C 0.8298(6) 0.0960(2) 0.8058(6) 0.0727(14) Uani 1 1 d U . . C43 C 0.7697(6) 0.0626(3) 0.8470(7) 0.0802(15) Uani 1 1 d U . . H43 H 0.8075 0.0440 0.9040 0.096 Uiso 1 1 calc R . . C42 C 0.6582(6) 0.0571(3) 0.8054(7) 0.0938(16) Uani 1 1 d U . . H42 H 0.6187 0.0353 0.8338 0.113 Uiso 1 1 calc R . . C47 C 0.6056(7) 0.0849(4) 0.7197(8) 0.1006(16) Uani 1 1 d U . . Cd1 Cd 0.17761(3) 0.070659(13) -0.05717(4) 0.05872(19) Uani 1 1 d U . . N1 N 0.3318(4) 0.10776(14) -0.0875(4) 0.0554(10) Uani 1 1 d U . . N4 N 0.9044(4) 0.26357(13) -0.0539(4) 0.0532(9) Uani 1 1 d U . . N3 N 1.4997(5) 0.1881(2) 0.4282(6) 0.0941(16) Uani 1 1 d U . . N2 N 0.8283(4) 0.50628(13) -0.3517(4) 0.0521(10) Uani 1 1 d U . . O1 O 0.1929(3) 0.09546(16) 0.1506(4) 0.0761(11) Uani 1 1 d U . . O2 O 0.2981(4) 0.04214(14) 0.1191(4) 0.0716(10) Uani 1 1 d U . . O5 O 0.4875(5) 0.0770(2) 0.6891(6) 0.1201(15) Uani 1 1 d U . . O4 O 1.0112(7) 0.1274(3) 0.8166(6) 0.153(3) Uani 1 1 d U . . 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 O3 0.049(2) 0.126(4) 0.076(3) -0.012(2) -0.004(2) 0.005(2) C34 0.071(3) 0.107(4) 0.057(3) -0.016(3) -0.005(3) -0.013(3) C1 0.048(2) 0.058(2) 0.063(3) 0.002(2) -0.006(2) 0.006(2) C2 0.045(2) 0.068(2) 0.067(2) 0.011(2) 0.005(2) 0.004(2) C3 0.041(2) 0.061(2) 0.063(3) 0.013(2) 0.002(2) 0.006(2) C4 0.047(2) 0.053(2) 0.049(2) 0.0019(19) 0.0008(18) 0.0037(19) C5 0.052(2) 0.051(2) 0.062(3) 0.006(2) -0.009(2) 0.003(2) C6 0.048(2) 0.051(2) 0.050(2) 0.0032(19) -0.0035(19) 0.0015(19) C11 0.062(2) 0.052(2) 0.059(2) 0.010(2) -0.018(2) -0.008(2) C10 0.062(2) 0.052(2) 0.059(2) 0.012(2) -0.015(2) -0.010(2) C9 0.046(2) 0.045(2) 0.052(2) 0.0007(18) -0.0069(18) 0.0016(17) C8 0.045(2) 0.066(2) 0.049(2) 0.003(2) -0.0063(19) 0.000(2) C7 0.049(2) 0.067(2) 0.051(2) 0.013(2) 0.000(2) 0.000(2) C23 0.042(2) 0.044(2) 0.053(2) 0.0012(18) -0.0043(18) 0.0019(17) C28 0.051(2) 0.044(2) 0.062(2) -0.0054(19) -0.008(2) 0.0086(19) C27 0.047(2) 0.048(2) 0.058(2) -0.0049(19) -0.007(2) 0.0007(19) C26 0.037(2) 0.053(2) 0.050(2) 0.0019(18) 0.0059(18) 0.0040(18) C25 0.041(2) 0.046(2) 0.051(2) -0.0013(18) 0.0026(18) 0.0057(18) C24 0.044(2) 0.045(2) 0.049(2) -0.0031(18) 0.0005(18) 0.0006(18) C30 0.059(3) 0.080(3) 0.065(3) 0.000(2) -0.004(2) 0.012(2) C29 0.040(2) 0.061(2) 0.058(2) 0.004(2) -0.0011(19) 0.0040(19) C33 0.052(2) 0.084(3) 0.073(3) -0.003(3) -0.002(2) 0.017(2) C32 0.061(3) 0.099(3) 0.090(3) -0.001(3) -0.006(3) 0.024(3) C12 0.044(2) 0.0404(19) 0.055(2) -0.0016(18) -0.0089(18) 0.0022(17) C13 0.043(2) 0.047(2) 0.065(2) 0.0009(19) -0.0020(19) -0.0010(18) C14 0.040(2) 0.046(2) 0.069(3) -0.002(2) 0.001(2) 0.0073(18) C15 0.039(2) 0.042(2) 0.057(2) -0.0029(18) -0.0030(18) 0.0044(17) C16 0.043(2) 0.047(2) 0.065(2) 0.003(2) 0.004(2) 0.0081(18) C17 0.045(2) 0.048(2) 0.063(2) 0.0001(19) -0.0007(19) 0.0119(18) C18 0.040(2) 0.042(2) 0.053(2) -0.0011(18) -0.0037(18) 0.0063(17) C19 0.048(2) 0.057(2) 0.086(3) 0.013(2) 0.007(2) 0.010(2) C22 0.048(2) 0.052(2) 0.071(3) 0.007(2) 0.009(2) 0.015(2) C21 0.052(2) 0.052(2) 0.069(3) 0.011(2) 0.012(2) 0.010(2) C35 0.043(2) 0.103(3) 0.061(3) -0.018(2) 0.006(2) -0.010(2) C36 0.044(2) 0.131(4) 0.061(3) -0.024(3) 0.003(2) 0.000(3) C41 0.052(3) 0.153(4) 0.071(3) -0.028(3) -0.003(2) 0.012(3) C40 0.061(3) 0.172(4) 0.072(3) -0.032(3) -0.001(3) 0.020(3) C38 0.065(3) 0.165(4) 0.073(3) -0.023(3) -0.004(3) 0.022(3) C37 0.057(3) 0.144(3) 0.067(3) -0.023(3) 0.003(2) 0.010(3) C20 0.052(3) 0.063(3) 0.091(3) 0.018(3) 0.005(3) 0.017(2) C31 0.073(3) 0.098(3) 0.074(3) 0.000(3) -0.016(3) 0.016(3) C39 0.063(3) 0.176(4) 0.070(3) -0.029(3) -0.006(3) 0.023(3) C46 0.088(3) 0.138(4) 0.068(3) -0.013(3) -0.015(3) 0.039(3) C45 0.095(3) 0.120(4) 0.066(3) -0.011(3) -0.008(3) 0.020(3) C44 0.069(3) 0.089(3) 0.054(3) -0.017(3) -0.011(2) 0.010(3) C43 0.057(3) 0.110(3) 0.069(3) -0.018(3) -0.004(2) 0.012(3) C42 0.067(3) 0.137(4) 0.074(3) -0.027(3) -0.002(3) 0.012(3) C47 0.067(3) 0.159(4) 0.071(3) -0.032(3) -0.007(3) 0.025(3) Cd1 0.0370(2) 0.0659(3) 0.0720(3) -0.0299(2) 0.00411(18) -0.01027(16) N1 0.0399(19) 0.065(2) 0.062(2) 0.0016(19) 0.0073(17) 0.0033(17) N4 0.0480(18) 0.0437(17) 0.062(2) 0.0038(16) -0.0120(16) 0.0008(15) N3 0.069(3) 0.111(4) 0.093(3) 0.006(3) -0.021(3) 0.021(3) N2 0.048(2) 0.051(2) 0.055(2) 0.0103(18) 0.0001(18) 0.0087(18) O1 0.0460(19) 0.112(3) 0.068(2) -0.017(2) 0.0005(17) 0.004(2) O2 0.068(2) 0.081(2) 0.064(2) -0.0106(19) 0.0015(18) -0.0098(19) O5 0.077(3) 0.196(3) 0.081(3) -0.027(3) -0.007(2) 0.026(3) O4 0.180(6) 0.170(6) 0.105(4) -0.021(4) 0.013(4) -0.122(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C34 1.255(9) . ? O3 Cd1 2.172(5) 1_656 ? C34 O4 1.224(9) . ? C34 C44 1.484(10) . ? C1 N1 1.338(7) . ? C1 C5 1.365(8) . ? C1 H1 0.9300 . ? C2 N1 1.339(7) . ? C2 C3 1.366(8) . ? C2 H2 0.9300 . ? C3 C4 1.388(7) . ? C3 H3 0.9300 . ? C4 C5 1.396(7) . ? C4 C6 1.467(7) . ? C5 H5 0.9300 . ? C6 C11 1.379(8) . ? C6 C7 1.400(7) . ? C11 C10 1.379(8) . ? C11 H11 0.9300 . ? C10 C9 1.383(7) . ? C10 H10 0.9300 . ? C9 C8 1.374(8) . ? C9 N4 1.413(7) . ? C8 C7 1.376(8) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C23 C24 1.376(7) . ? C23 C28 1.382(7) . ? C23 N4 1.424(6) . ? C28 C27 1.382(7) . ? C28 H28 0.9300 . ? C27 C26 1.387(7) . ? C27 H27 0.9300 . ? C26 C25 1.392(7) . ? C26 C29 1.486(7) . ? C25 C24 1.389(7) . ? C25 H25 0.9300 . ? C24 H24 0.9300 . ? C30 C29 1.377(8) . ? C30 C31 1.381(9) . ? C30 H30 0.9300 . ? C29 C33 1.380(8) . ? C33 C32 1.392(9) . ? C33 H33 0.9300 . ? C32 N3 1.330(10) . ? C32 H32 0.9300 . ? C12 C17 1.385(8) . ? C12 C13 1.391(7) . ? C12 N4 1.426(6) . ? C13 C14 1.377(7) . ? C13 H13 0.9300 . ? C14 C15 1.388(8) . ? C14 H14 0.9300 . ? C15 C16 1.398(7) . ? C15 C18 1.488(7) . ? C16 C17 1.384(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C22 1.373(8) . ? C18 C19 1.381(7) . ? C19 C20 1.391(8) . ? C19 H19 0.9300 . ? C22 C21 1.387(7) . ? C22 H22 0.9300 . ? C21 N2 1.323(7) . ? C21 H21 0.9300 . ? C35 O2 1.243(8) . ? C35 O1 1.266(8) . ? C35 C36 1.491(9) . ? C36 C37 1.380(10) . ? C36 C41 1.393(10) . ? C41 C40 1.367(10) . ? C41 H41 0.9300 . ? C40 C39 1.409(11) . ? C40 H40 0.9300 . ? C38 C39 1.349(11) . ? C38 C37 1.385(10) . ? C38 H38 0.9300 . ? C37 H37 0.9300 . ? C20 N2 1.320(8) . ? C20 H20 0.9300 . ? C31 N3 1.331(10) . ? C31 H31 0.9300 . ? C39 O5 1.406(10) . ? C46 C47 1.282(13) . ? C46 C45 1.425(12) . ? C46 H46 0.9300 . ? C45 C44 1.369(10) . ? C45 H45 0.9300 . ? C44 C43 1.409(11) . ? C43 C42 1.356(10) . ? C43 H43 0.9300 . ? C42 C47 1.376(13) . ? C42 H42 0.9300 . ? C47 O5 1.428(10) . ? Cd1 O3 2.172(5) 1_454 ? Cd1 N1 2.271(4) . ? Cd1 N2 2.310(4) 2_644 ? Cd1 O1 2.357(4) . ? Cd1 O2 2.392(4) . ? N2 Cd1 2.310(4) 2_654 ? 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 C34 O3 Cd1 112.3(5) . 1_656 ? O4 C34 O3 121.5(8) . . ? O4 C34 C44 123.5(8) . . ? O3 C34 C44 114.9(7) . . ? N1 C1 C5 123.1(5) . . ? N1 C1 H1 118.4 . . ? C5 C1 H1 118.4 . . ? N1 C2 C3 123.8(5) . . ? N1 C2 H2 118.1 . . ? C3 C2 H2 118.1 . . ? C2 C3 C4 120.2(5) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 115.8(5) . . ? C3 C4 C6 121.6(5) . . ? C5 C4 C6 122.6(5) . . ? C1 C5 C4 120.6(5) . . ? C1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C11 C6 C7 116.9(5) . . ? C11 C6 C4 122.3(5) . . ? C7 C6 C4 120.8(5) . . ? C10 C11 C6 121.7(5) . . ? C10 C11 H11 119.1 . . ? C6 C11 H11 119.1 . . ? C11 C10 C9 120.6(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C8 C9 C10 118.5(5) . . ? C8 C9 N4 120.5(4) . . ? C10 C9 N4 121.0(5) . . ? C9 C8 C7 120.8(5) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C7 C6 121.4(5) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C24 C23 C28 119.3(4) . . ? C24 C23 N4 120.0(4) . . ? C28 C23 N4 120.6(4) . . ? C23 C28 C27 120.3(5) . . ? C23 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C27 C26 121.5(5) . . ? C28 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? C27 C26 C25 117.4(5) . . ? C27 C26 C29 120.9(5) . . ? C25 C26 C29 121.7(5) . . ? C24 C25 C26 121.5(4) . . ? C24 C25 H25 119.3 . . ? C26 C25 H25 119.3 . . ? C23 C24 C25 120.0(5) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C29 C30 C31 119.6(6) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C30 C29 C33 117.0(5) . . ? C30 C29 C26 121.6(5) . . ? C33 C29 C26 121.4(5) . . ? C29 C33 C32 119.2(6) . . ? C29 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? N3 C32 C33 124.2(7) . . ? N3 C32 H32 117.9 . . ? C33 C32 H32 117.9 . . ? C17 C12 C13 118.7(5) . . ? C17 C12 N4 120.2(5) . . ? C13 C12 N4 121.1(5) . . ? C14 C13 C12 120.5(5) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.2(5) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C14 C15 C16 118.3(5) . . ? C14 C15 C18 121.7(4) . . ? C16 C15 C18 120.0(5) . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C12 121.0(5) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C22 C18 C19 116.3(5) . . ? C22 C18 C15 121.4(4) . . ? C19 C18 C15 122.3(5) . . ? C18 C19 C20 119.7(6) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C18 C22 C21 120.3(5) . . ? C18 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? N2 C21 C22 123.2(5) . . ? N2 C21 H21 118.4 . . ? C22 C21 H21 118.4 . . ? O2 C35 O1 122.6(6) . . ? O2 C35 C36 118.6(6) . . ? O1 C35 C36 118.7(6) . . ? C37 C36 C41 119.1(6) . . ? C37 C36 C35 121.0(6) . . ? C41 C36 C35 119.8(6) . . ? C40 C41 C36 120.8(7) . . ? C40 C41 H41 119.6 . . ? C36 C41 H41 119.6 . . ? C41 C40 C39 118.1(8) . . ? C41 C40 H40 120.9 . . ? C39 C40 H40 120.9 . . ? C39 C38 C37 119.0(7) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? C36 C37 C38 120.8(7) . . ? C36 C37 H37 119.6 . . ? C38 C37 H37 119.6 . . ? N2 C20 C19 123.5(5) . . ? N2 C20 H20 118.3 . . ? C19 C20 H20 118.3 . . ? N3 C31 C30 124.5(7) . . ? N3 C31 H31 117.8 . . ? C30 C31 H31 117.8 . . ? C38 C39 O5 119.8(7) . . ? C38 C39 C40 121.7(7) . . ? O5 C39 C40 118.5(7) . . ? C47 C46 C45 120.3(8) . . ? C47 C46 H46 119.9 . . ? C45 C46 H46 119.9 . . ? C44 C45 C46 118.8(9) . . ? C44 C45 H45 120.6 . . ? C46 C45 H45 120.6 . . ? C45 C44 C43 118.1(7) . . ? C45 C44 C34 122.2(8) . . ? C43 C44 C34 119.6(6) . . ? C42 C43 C44 121.6(8) . . ? C42 C43 H43 119.2 . . ? C44 C43 H43 119.2 . . ? C43 C42 C47 117.6(10) . . ? C43 C42 H42 121.2 . . ? C47 C42 H42 121.2 . . ? C46 C47 C42 123.7(8) . . ? C46 C47 O5 124.2(9) . . ? C42 C47 O5 112.0(10) . . ? O3 Cd1 N1 143.88(19) 1_454 . ? O3 Cd1 N2 90.25(17) 1_454 2_644 ? N1 Cd1 N2 113.28(16) . 2_644 ? O3 Cd1 O1 91.49(17) 1_454 . ? N1 Cd1 O1 90.26(16) . . ? N2 Cd1 O1 134.92(18) 2_644 . ? O3 Cd1 O2 124.63(18) 1_454 . ? N1 Cd1 O2 84.97(15) . . ? N2 Cd1 O2 87.75(15) 2_644 . ? O1 Cd1 O2 55.22(16) . . ? C1 N1 C2 116.5(5) . . ? C1 N1 Cd1 122.7(3) . . ? C2 N1 Cd1 119.7(4) . . ? C9 N4 C23 119.6(4) . . ? C9 N4 C12 119.6(4) . . ? C23 N4 C12 119.8(4) . . ? C32 N3 C31 115.4(6) . . ? C20 N2 C21 116.9(5) . . ? C20 N2 Cd1 125.9(3) . 2_654 ? C21 N2 Cd1 117.1(4) . 2_654 ? C35 O1 Cd1 91.4(4) . . ? C35 O2 Cd1 90.4(4) . . ? C39 O5 C47 116.6(7) . . ? 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 _platon_squeeze_void_content 1 0.500 0.000 0.000 10 1 ' ' 2 0.500 0.500 0.500 10 1 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.508 _refine_diff_density_min -1.452 _refine_diff_density_rms 0.085 _database_code_depnum_ccdc_archive 'CCDC 957214' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C47 H32 Co N4 O5' _chemical_formula_sum 'C47 H32 Co N4 O5' _chemical_formula_weight 791.70 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' Co Co 0.3494 0.9721 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6417(11) _cell_length_b 32.110(3) _cell_length_c 10.8370(11) _cell_angle_alpha 90.00 _cell_angle_beta 98.525(2) _cell_angle_gamma 90.00 _cell_volume 4006.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6813 _cell_measurement_theta_min 1.77 _cell_measurement_theta_max 24.71 _exptl_crystal_description solid _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1636 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 0.899 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28750 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_sigmaI/netI 0.0784 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.71 _reflns_number_total 6813 _reflns_number_gt 5344 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0529P)^2^+3.6024P] 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 6813 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1401 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.4241(4) 0.70899(16) -0.4396(4) 0.0720(12) Uani 1 1 d . . . H1 H -0.4322 0.7171 -0.5228 0.086 Uiso 1 1 calc R . . C2 C -0.3281(3) 0.72327(13) -0.3613(3) 0.0535(9) Uani 1 1 d . . . H2 H -0.2738 0.7400 -0.3924 0.064 Uiso 1 1 calc R . . C3 C -0.3976(3) 0.68711(13) -0.2007(4) 0.0605(11) Uani 1 1 d . . . H3 H -0.3924 0.6785 -0.1180 0.073 Uiso 1 1 calc R . . C4 C -0.4897(3) 0.67441(15) -0.2870(5) 0.0739(13) Uani 1 1 d . . . H4 H -0.5450 0.6572 -0.2594 0.089 Uiso 1 1 calc R . . C5 C -0.3129(3) 0.71256(10) -0.2366(3) 0.0362(7) Uani 1 1 d . . . C6 C -0.2123(2) 0.72727(9) -0.1471(3) 0.0319(7) Uani 1 1 d . . . C7 C -0.1608(3) 0.70189(9) -0.0509(3) 0.0354(7) Uani 1 1 d . . . H7 H -0.1911 0.6755 -0.0413 0.042 Uiso 1 1 calc R . . C8 C -0.0654(3) 0.71513(9) 0.0309(3) 0.0337(7) Uani 1 1 d . . . H8 H -0.0329 0.6978 0.0956 0.040 Uiso 1 1 calc R . . C9 C -0.0178(2) 0.75425(9) 0.0166(3) 0.0298(6) Uani 1 1 d . . . C10 C -0.0692(3) 0.78032(9) -0.0778(3) 0.0365(7) Uani 1 1 d . . . H10 H -0.0397 0.8069 -0.0866 0.044 Uiso 1 1 calc R . . C11 C -0.1650(3) 0.76647(9) -0.1587(3) 0.0361(7) Uani 1 1 d . . . H11 H -0.1984 0.7839 -0.2225 0.043 Uiso 1 1 calc R . . C12 C 0.1943(3) 0.71329(10) -0.0033(3) 0.0382(7) Uani 1 1 d . . . H12 H 0.1364 0.7134 -0.0725 0.046 Uiso 1 1 calc R . . H13 H 0.2557 0.8185 0.0801 0.046 Uiso 1 1 d R . . H14 H 0.2782 0.8857 0.1558 0.046 Uiso 1 1 d R . . H16 H -0.0249 0.8775 0.2863 0.046 Uiso 1 1 d R . . H17 H -0.0482 0.8104 0.2116 0.046 Uiso 1 1 d R . . H20 H -0.0201 0.9450 0.2916 0.046 Uiso 1 1 d R . . H21 H 0.0108 1.0106 0.3697 0.046 Uiso 1 1 d R . . H22 H 0.3441 0.9998 0.3767 0.046 Uiso 1 1 d R . . H23 H 0.3218 0.9345 0.2942 0.046 Uiso 1 1 d R . . C13 C 0.1996(2) 0.83026(9) 0.1218(3) 0.0329(7) Uani 1 1 d . . . C14 C 0.2128(3) 0.87045(9) 0.1676(3) 0.0345(7) Uani 1 1 d . . . C15 C 0.1307(2) 0.88849(9) 0.2311(3) 0.0300(6) Uani 1 1 d . . . C16 C 0.0325(3) 0.86561(9) 0.2455(3) 0.0375(7) Uani 1 1 d . . . C17 C 0.0182(3) 0.82539(9) 0.2003(3) 0.0373(7) Uani 1 1 d . . . C18 C 0.1017(2) 0.80710(9) 0.1388(3) 0.0295(6) Uani 1 1 d . . . C19 C 0.1479(3) 0.93115(9) 0.2824(3) 0.0314(7) Uani 1 1 d . . . C20 C 0.0550(3) 0.95550(9) 0.3071(3) 0.0393(7) Uani 1 1 d . . . C21 C 0.0744(3) 0.99512(10) 0.3546(3) 0.0387(7) Uani 1 1 d . . . C22 C 0.2695(3) 0.98892(11) 0.3577(4) 0.0477(9) Uani 1 1 d . . . C23 C 0.2567(3) 0.94936(10) 0.3092(3) 0.0435(8) Uani 1 1 d . . . C24 C 1.1296(3) 0.60280(9) 0.2203(3) 0.0354(7) Uani 1 1 d . . . C25 C 1.1933(3) 0.62522(11) 0.3158(3) 0.0481(9) Uani 1 1 d . . . H25 H 1.1565 0.6456 0.3568 0.058 Uiso 1 1 calc R . . C26 C 1.3102(3) 0.61793(12) 0.3513(3) 0.0525(9) Uani 1 1 d . . . H26 H 1.3525 0.6338 0.4141 0.063 Uiso 1 1 calc R . . C27 C 1.3634(3) 0.58715(12) 0.2931(3) 0.0464(8) Uani 1 1 d . . . C28 C 1.3031(3) 0.56401(11) 0.1982(3) 0.0464(8) Uani 1 1 d . . . H28 H 1.3400 0.5431 0.1595 0.056 Uiso 1 1 calc R . . C29 C 1.1867(3) 0.57242(10) 0.1614(3) 0.0423(8) Uani 1 1 d . . . H29 H 1.1456 0.5574 0.0958 0.051 Uiso 1 1 calc R . . C31 C 1.6395(3) 0.59342(15) 0.4771(4) 0.0653(12) Uani 1 1 d . . . H31 H 1.6744 0.6087 0.4199 0.078 Uiso 1 1 calc R . . C32 C 1.6955(3) 0.58827(15) 0.5976(3) 0.0602(11) Uani 1 1 d . . . H32 H 1.7673 0.6007 0.6221 0.072 Uiso 1 1 calc R . . C33 C 0.6765(3) 0.63767(9) 0.1515(3) 0.0364(7) Uani 1 1 d . . . H33 H 0.7502 0.6437 0.1935 0.044 Uiso 1 1 calc R . . C34 C 0.5865(3) 0.66541(10) 0.1607(3) 0.0383(7) Uani 1 1 d . . . H34 H 0.6009 0.6894 0.2084 0.046 Uiso 1 1 calc R . . C35 C 0.5518(3) 0.59392(10) 0.0303(3) 0.0403(8) Uani 1 1 d . . . H35 H 0.5383 0.5689 -0.0126 0.048 Uiso 1 1 calc R . . C36 C 0.4601(3) 0.61994(10) 0.0353(3) 0.0396(8) Uani 1 1 d . . . H36 H 0.3866 0.6125 -0.0044 0.048 Uiso 1 1 calc R . . C37 C 0.4754(2) 0.65756(9) 0.0994(3) 0.0317(7) Uani 1 1 d . . . C38 C 0.3769(3) 0.68656(9) 0.0993(3) 0.0324(7) Uani 1 1 d . . . C39 C 0.2878(3) 0.68743(11) -0.0007(3) 0.0402(8) Uani 1 1 d . . . H39 H 0.2918 0.6698 -0.0681 0.048 Uiso 1 1 calc R . . C41 C 0.1853(2) 0.73941(9) 0.0968(3) 0.0301(6) Uani 1 1 d . . . C42 C 0.2736(3) 0.73892(10) 0.1973(3) 0.0425(8) Uani 1 1 d . . . H42 H 0.2692 0.7563 0.2651 0.051 Uiso 1 1 calc R . . C43 C 0.3678(3) 0.71311(10) 0.1982(3) 0.0414(8) Uani 1 1 d . . . H43 H 0.4265 0.7135 0.2665 0.050 Uiso 1 1 calc R . . C73 C 1.0011(3) 0.61051(10) 0.1851(3) 0.0427(8) Uani 1 1 d . . . C74 C 1.5323(3) 0.57586(13) 0.4421(3) 0.0503(9) Uani 1 1 d . . . C77 C 1.7033(3) 0.55942(13) 0.8123(3) 0.0494(9) Uani 1 1 d . . . C81 C 1.4805(3) 0.55306(13) 0.5251(3) 0.0532(9) Uani 1 1 d . . . H81 H 1.4068 0.5419 0.5014 0.064 Uiso 1 1 calc R . . C82 C 1.5383(3) 0.54675(12) 0.6444(3) 0.0512(9) Uani 1 1 d . . . H82 H 1.5046 0.5302 0.6998 0.061 Uiso 1 1 calc R . . C83 C 1.6452(3) 0.56462(11) 0.6822(3) 0.0450(8) Uani 1 1 d . . . Co1 Co 0.79961(3) 0.569493(12) 0.03539(4) 0.03026(14) Uani 1 1 d . . . N1 N 0.0873(2) 0.76570(7) 0.0943(2) 0.0340(6) Uani 1 1 d . . . N2 N 0.6613(2) 0.60257(7) 0.0845(2) 0.0347(6) Uani 1 1 d . . . N3 N 0.1799(2) 1.01219(8) 0.3798(2) 0.0365(6) Uani 1 1 d . . . N4 N -0.5053(3) 0.68480(13) -0.4057(4) 0.0734(11) Uani 1 1 d . . . O1 O 1.4830(2) 0.58020(10) 0.3191(2) 0.0667(8) Uani 1 1 d . . . O2 O 1.7924(2) 0.58112(9) 0.8516(2) 0.0588(7) Uani 1 1 d . . . O3 O 1.6611(2) 0.53540(8) 0.8848(2) 0.0555(7) Uani 1 1 d . . . O4 O 0.9537(2) 0.59035(8) 0.0902(2) 0.0539(6) Uani 1 1 d . . . O5 O 0.9510(2) 0.63456(10) 0.2457(3) 0.0743(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.063(3) 0.104(4) 0.042(2) -0.012(2) -0.014(2) -0.008(3) C2 0.046(2) 0.072(3) 0.039(2) -0.0043(18) -0.0048(16) -0.0142(18) C3 0.043(2) 0.081(3) 0.052(2) 0.005(2) -0.0092(18) -0.0237(19) C4 0.045(2) 0.085(3) 0.087(4) 0.002(3) -0.008(2) -0.025(2) C5 0.0269(16) 0.0421(18) 0.0375(18) -0.0070(14) -0.0019(13) -0.0003(13) C6 0.0262(15) 0.0346(17) 0.0346(16) -0.0022(13) 0.0034(13) -0.0013(12) C7 0.0338(17) 0.0318(17) 0.0396(18) 0.0014(13) 0.0027(14) -0.0063(13) C8 0.0336(17) 0.0338(17) 0.0313(16) 0.0028(13) -0.0030(13) 0.0014(13) C9 0.0275(15) 0.0290(16) 0.0301(16) -0.0055(12) -0.0047(12) 0.0011(12) C10 0.0346(17) 0.0266(16) 0.0443(19) 0.0032(13) -0.0071(14) -0.0018(12) C11 0.0355(17) 0.0336(17) 0.0357(17) 0.0070(13) -0.0068(14) 0.0026(13) C12 0.0333(17) 0.051(2) 0.0256(16) -0.0075(14) -0.0103(13) 0.0073(14) C13 0.0281(16) 0.0357(17) 0.0341(17) -0.0056(13) 0.0014(13) 0.0034(12) C14 0.0298(16) 0.0340(17) 0.0385(18) 0.0002(13) 0.0013(13) -0.0029(12) C15 0.0303(16) 0.0277(15) 0.0296(16) -0.0022(12) -0.0036(12) 0.0009(12) C16 0.0333(17) 0.0339(17) 0.0458(19) -0.0095(14) 0.0073(14) -0.0013(13) C17 0.0322(17) 0.0331(17) 0.0465(19) -0.0035(14) 0.0061(14) -0.0054(13) C18 0.0280(15) 0.0285(16) 0.0281(15) -0.0011(12) -0.0085(12) 0.0029(12) C19 0.0347(17) 0.0287(16) 0.0294(16) -0.0029(12) -0.0002(13) -0.0016(12) C20 0.0326(17) 0.0315(17) 0.052(2) -0.0062(14) 0.0006(15) -0.0073(13) C21 0.0334(17) 0.0352(18) 0.0465(19) -0.0083(14) 0.0023(15) 0.0000(13) C22 0.0301(18) 0.048(2) 0.062(2) -0.0114(17) -0.0032(16) -0.0097(15) C23 0.0317(17) 0.0397(19) 0.057(2) -0.0104(16) 0.0000(15) 0.0011(14) C24 0.0359(17) 0.0330(17) 0.0335(17) 0.0049(13) -0.0077(13) -0.0028(13) C25 0.044(2) 0.053(2) 0.042(2) -0.0112(16) -0.0103(16) 0.0028(16) C26 0.048(2) 0.068(3) 0.0357(19) -0.0108(17) -0.0138(16) -0.0073(18) C27 0.0345(18) 0.073(2) 0.0286(17) 0.0083(17) -0.0036(14) 0.0032(17) C28 0.044(2) 0.052(2) 0.041(2) -0.0027(16) 0.0013(16) 0.0062(16) C29 0.0422(19) 0.043(2) 0.0372(18) -0.0019(14) -0.0079(15) -0.0088(15) C31 0.044(2) 0.108(4) 0.042(2) 0.019(2) -0.0018(17) -0.005(2) C32 0.041(2) 0.101(3) 0.035(2) 0.007(2) -0.0080(16) -0.007(2) C33 0.0325(17) 0.0349(17) 0.0390(18) 0.0000(14) -0.0041(14) 0.0023(13) C34 0.0383(18) 0.0305(17) 0.0427(19) -0.0079(13) -0.0050(15) 0.0045(13) C35 0.0350(18) 0.0328(18) 0.052(2) -0.0108(14) 0.0033(15) -0.0013(13) C36 0.0326(17) 0.0370(18) 0.048(2) -0.0059(14) 0.0009(15) -0.0008(13) C37 0.0310(16) 0.0313(16) 0.0312(16) 0.0000(12) -0.0009(13) 0.0024(12) C38 0.0313(16) 0.0320(16) 0.0317(16) -0.0029(12) -0.0024(13) 0.0025(12) C39 0.0390(18) 0.052(2) 0.0269(16) -0.0103(14) -0.0042(14) 0.0085(15) C41 0.0297(16) 0.0281(15) 0.0299(16) -0.0022(12) -0.0045(12) 0.0017(12) C42 0.045(2) 0.0415(19) 0.0349(18) -0.0161(14) -0.0134(15) 0.0112(15) C43 0.0398(19) 0.0407(19) 0.0368(18) -0.0125(14) -0.0174(15) 0.0115(14) C73 0.048(2) 0.0336(18) 0.042(2) 0.0042(15) -0.0078(16) -0.0004(15) C74 0.037(2) 0.083(3) 0.0282(18) 0.0009(17) -0.0051(15) 0.0122(17) C77 0.041(2) 0.066(2) 0.039(2) -0.0013(18) 0.0004(17) 0.0233(18) C81 0.040(2) 0.075(3) 0.041(2) 0.0005(18) -0.0071(16) -0.0023(18) C82 0.049(2) 0.061(2) 0.041(2) 0.0081(17) 0.0002(17) 0.0052(17) C83 0.0376(19) 0.066(2) 0.0287(17) -0.0005(15) -0.0048(14) 0.0140(16) Co1 0.0312(2) 0.0275(2) 0.0294(2) 0.00008(16) -0.00441(17) 0.00498(16) N1 0.0294(13) 0.0281(13) 0.0397(15) -0.0085(11) -0.0106(11) 0.0064(10) N2 0.0332(14) 0.0294(14) 0.0413(15) 0.0004(11) 0.0049(12) 0.0043(10) N3 0.0336(15) 0.0340(14) 0.0392(15) -0.0054(11) -0.0031(12) -0.0039(11) N4 0.050(2) 0.091(3) 0.071(3) -0.019(2) -0.0181(19) -0.0176(19) O1 0.0368(14) 0.131(3) 0.0293(13) 0.0070(14) -0.0063(11) 0.0144(14) O2 0.0385(14) 0.102(2) 0.0320(13) -0.0002(13) -0.0078(11) 0.0012(14) O3 0.0746(18) 0.0540(16) 0.0344(13) -0.0005(12) -0.0040(12) 0.0186(13) O4 0.0416(14) 0.0601(16) 0.0540(16) -0.0122(13) -0.0126(12) -0.0090(11) O5 0.0505(16) 0.082(2) 0.083(2) -0.0309(17) -0.0155(15) 0.0203(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.317(6) . ? C1 C2 1.377(5) . ? C1 H1 0.9300 . ? C2 C5 1.380(5) . ? C2 H2 0.9300 . ? C3 C4 1.376(5) . ? C3 C5 1.380(5) . ? C3 H3 0.9300 . ? C4 N4 1.316(6) . ? C4 H4 0.9300 . ? C5 C6 1.483(4) . ? C6 C11 1.388(4) . ? C6 C7 1.388(4) . ? C7 C8 1.381(4) . ? C7 H7 0.9300 . ? C8 C9 1.391(4) . ? C8 H8 0.9300 . ? C9 C10 1.387(4) . ? C9 N1 1.427(4) . ? C10 C11 1.385(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C39 1.366(4) . ? C12 C41 1.388(4) . ? C12 H12 0.9300 . ? C13 C14 1.383(4) . ? C13 C18 1.396(4) . ? C13 H13 0.9276 . ? C14 C15 1.385(4) . ? C14 H14 0.9289 . ? C15 C16 1.387(4) . ? C15 C19 1.480(4) . ? C16 C17 1.383(4) . ? C16 H16 0.9352 . ? C17 C18 1.388(4) . ? C17 H17 0.9343 . ? C18 N1 1.415(4) . ? C19 C23 1.386(4) . ? C19 C20 1.393(4) . ? C20 C21 1.378(4) . ? C20 H20 0.9285 . ? C21 N3 1.336(4) . ? C21 H21 0.9267 . ? C22 N3 1.334(4) . ? C22 C23 1.374(5) . ? C22 H22 0.9301 . ? C23 H23 0.9308 . ? C24 C25 1.382(4) . ? C24 C29 1.387(5) . ? C24 C73 1.509(4) . ? C25 C26 1.379(5) . ? C25 H25 0.9300 . ? C26 C27 1.369(5) . ? C26 H26 0.9300 . ? C27 C28 1.374(5) . ? C27 O1 1.398(4) . ? C28 C29 1.382(5) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C31 C74 1.371(5) . ? C31 C32 1.380(5) . ? C31 H31 0.9300 . ? C32 C83 1.385(5) . ? C32 H32 0.9300 . ? C33 N2 1.338(4) . ? C33 C34 1.390(4) . ? C33 H33 0.9300 . ? C34 C37 1.386(4) . ? C34 H34 0.9300 . ? C35 N2 1.350(4) . ? C35 C36 1.363(4) . ? C35 H35 0.9300 . ? C36 C37 1.392(4) . ? C36 H36 0.9300 . ? C37 C38 1.477(4) . ? C38 C39 1.384(4) . ? C38 C43 1.386(4) . ? C39 H39 0.9300 . ? C41 C42 1.382(4) . ? C41 N1 1.417(4) . ? C42 C43 1.373(4) . ? C42 H42 0.9300 . ? C43 H43 0.9300 . ? C73 O5 1.217(4) . ? C73 O4 1.270(4) . ? C74 O1 1.377(4) . ? C74 C81 1.368(5) . ? C77 O3 1.252(5) . ? C77 O2 1.269(5) . ? C77 C83 1.480(5) . ? C81 C82 1.381(5) . ? C81 H81 0.9300 . ? C82 C83 1.377(5) . ? C82 H82 0.9300 . ? Co1 O4 1.925(2) . ? Co1 O2 2.016(2) 1_454 ? Co1 N3 2.055(2) 2_645 ? Co1 N2 2.064(2) . ? Co1 O3 2.384(3) 1_454 ? N3 Co1 2.055(2) 2_655 ? O2 Co1 2.016(2) 1_656 ? O3 Co1 2.384(3) 1_656 ? 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 C1 C2 125.1(4) . . ? N4 C1 H1 117.4 . . ? C2 C1 H1 117.4 . . ? C5 C2 C1 119.6(4) . . ? C5 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C5 120.0(4) . . ? C4 C3 H3 120.0 . . ? C5 C3 H3 120.0 . . ? N4 C4 C3 124.8(4) . . ? N4 C4 H4 117.6 . . ? C3 C4 H4 117.6 . . ? C2 C5 C3 115.5(3) . . ? C2 C5 C6 122.4(3) . . ? C3 C5 C6 122.1(3) . . ? C11 C6 C7 117.9(3) . . ? C11 C6 C5 121.1(3) . . ? C7 C6 C5 121.1(3) . . ? C8 C7 C6 121.2(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 120.1(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 119.5(3) . . ? C10 C9 N1 121.2(3) . . ? C8 C9 N1 119.2(3) . . ? C9 C10 C11 119.4(3) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C6 C11 C10 121.8(3) . . ? C6 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C39 C12 C41 120.2(3) . . ? C39 C12 H12 119.9 . . ? C41 C12 H12 119.9 . . ? C14 C13 C18 119.9(3) . . ? C14 C13 H13 120.4 . . ? C18 C13 H13 119.6 . . ? C15 C14 C13 121.4(3) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 118.4(3) . . ? C16 C15 C19 121.1(3) . . ? C14 C15 C19 120.6(3) . . ? C15 C16 C17 120.9(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 120.6(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.6 . . ? C17 C18 C13 118.8(3) . . ? C17 C18 N1 120.3(3) . . ? C13 C18 N1 120.9(3) . . ? C23 C19 C20 115.7(3) . . ? C23 C19 C15 122.5(3) . . ? C20 C19 C15 121.7(3) . . ? C19 C20 C21 120.1(3) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? N3 C21 C20 123.3(3) . . ? N3 C21 H21 118.5 . . ? C20 C21 H21 118.2 . . ? N3 C22 C23 122.9(3) . . ? N3 C22 H22 118.7 . . ? C23 C22 H22 118.5 . . ? C19 C23 C22 121.0(3) . . ? C19 C23 H23 119.2 . . ? C22 C23 H23 119.8 . . ? C25 C24 C29 118.1(3) . . ? C25 C24 C73 120.3(3) . . ? C29 C24 C73 121.6(3) . . ? C26 C25 C24 121.2(3) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 119.3(3) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C28 C27 C26 121.3(3) . . ? C28 C27 O1 116.6(3) . . ? C26 C27 O1 121.8(3) . . ? C27 C28 C29 118.7(3) . . ? C27 C28 H28 120.7 . . ? C29 C28 H28 120.7 . . ? C28 C29 C24 121.4(3) . . ? C28 C29 H29 119.3 . . ? C24 C29 H29 119.3 . . ? C74 C31 C32 119.7(4) . . ? C74 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C31 C32 C83 120.4(4) . . ? C31 C32 H32 119.8 . . ? C83 C32 H32 119.8 . . ? N2 C33 C34 122.5(3) . . ? N2 C33 H33 118.7 . . ? C34 C33 H33 118.7 . . ? C37 C34 C33 120.6(3) . . ? C37 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? N2 C35 C36 123.5(3) . . ? N2 C35 H35 118.3 . . ? C36 C35 H35 118.3 . . ? C35 C36 C37 120.5(3) . . ? C35 C36 H36 119.7 . . ? C37 C36 H36 119.7 . . ? C34 C37 C36 116.0(3) . . ? C34 C37 C38 123.7(3) . . ? C36 C37 C38 120.3(3) . . ? C39 C38 C43 117.3(3) . . ? C39 C38 C37 120.3(3) . . ? C43 C38 C37 122.4(3) . . ? C12 C39 C38 122.1(3) . . ? C12 C39 H39 119.0 . . ? C38 C39 H39 119.0 . . ? C42 C41 C12 118.4(3) . . ? C42 C41 N1 121.7(3) . . ? C12 C41 N1 119.9(3) . . ? C43 C42 C41 120.8(3) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C38 121.2(3) . . ? C42 C43 H43 119.4 . . ? C38 C43 H43 119.4 . . ? O5 C73 O4 125.2(3) . . ? O5 C73 C24 120.3(3) . . ? O4 C73 C24 114.6(3) . . ? O1 C74 C31 117.2(3) . . ? O1 C74 C81 122.0(3) . . ? C31 C74 C81 120.7(3) . . ? O3 C77 O2 120.4(3) . . ? O3 C77 C83 120.0(4) . . ? O2 C77 C83 119.5(4) . . ? C82 C81 C74 119.6(3) . . ? C82 C81 H81 120.2 . . ? C74 C81 H81 120.2 . . ? C81 C82 C83 120.7(3) . . ? C81 C82 H82 119.6 . . ? C83 C82 H82 119.6 . . ? C82 C83 C32 118.9(3) . . ? C82 C83 C77 120.1(3) . . ? C32 C83 C77 120.9(3) . . ? O4 Co1 O2 98.10(11) . 1_454 ? O4 Co1 N3 97.61(11) . 2_645 ? O2 Co1 N3 126.34(11) 1_454 2_645 ? O4 Co1 N2 117.97(11) . . ? O2 Co1 N2 103.86(10) 1_454 . ? N3 Co1 N2 112.89(10) 2_645 . ? O4 Co1 O3 151.17(10) . 1_454 ? O2 Co1 O3 58.90(10) 1_454 1_454 ? N3 Co1 O3 85.23(10) 2_645 1_454 ? N2 Co1 O3 86.45(9) . 1_454 ? C18 N1 C41 119.9(2) . . ? C18 N1 C9 119.4(2) . . ? C41 N1 C9 118.4(2) . . ? C33 N2 C35 116.7(3) . . ? C33 N2 Co1 121.8(2) . . ? C35 N2 Co1 120.3(2) . . ? C21 N3 C22 117.0(3) . . ? C21 N3 Co1 120.1(2) . 2_655 ? C22 N3 Co1 122.7(2) . 2_655 ? C1 N4 C4 114.9(3) . . ? C74 O1 C27 118.1(3) . . ? C77 O2 Co1 98.2(2) . 1_656 ? C77 O3 Co1 81.8(2) . 1_656 ? C73 O4 Co1 134.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C5 -0.8(7) . . . . ? C5 C3 C4 N4 -0.1(8) . . . . ? C1 C2 C5 C3 0.9(6) . . . . ? C1 C2 C5 C6 -179.3(4) . . . . ? C4 C3 C5 C2 -0.5(6) . . . . ? C4 C3 C5 C6 179.7(4) . . . . ? C2 C5 C6 C11 34.6(5) . . . . ? C3 C5 C6 C11 -145.6(4) . . . . ? C2 C5 C6 C7 -143.8(3) . . . . ? C3 C5 C6 C7 36.0(5) . . . . ? C11 C6 C7 C8 0.0(4) . . . . ? C5 C6 C7 C8 178.5(3) . . . . ? C6 C7 C8 C9 -1.1(5) . . . . ? C7 C8 C9 C10 2.1(4) . . . . ? C7 C8 C9 N1 -173.9(3) . . . . ? C8 C9 C10 C11 -2.0(5) . . . . ? N1 C9 C10 C11 173.9(3) . . . . ? C7 C6 C11 C10 0.1(5) . . . . ? C5 C6 C11 C10 -178.4(3) . . . . ? C9 C10 C11 C6 0.9(5) . . . . ? C18 C13 C14 C15 0.3(5) . . . . ? C13 C14 C15 C16 -1.6(5) . . . . ? C13 C14 C15 C19 178.3(3) . . . . ? C14 C15 C16 C17 1.6(5) . . . . ? C19 C15 C16 C17 -178.3(3) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C16 C17 C18 C13 -0.9(5) . . . . ? C16 C17 C18 N1 179.1(3) . . . . ? C14 C13 C18 C17 1.0(4) . . . . ? C14 C13 C18 N1 -179.1(3) . . . . ? C16 C15 C19 C23 157.1(3) . . . . ? C14 C15 C19 C23 -22.9(5) . . . . ? C16 C15 C19 C20 -22.7(5) . . . . ? C14 C15 C19 C20 157.4(3) . . . . ? C23 C19 C20 C21 0.4(5) . . . . ? C15 C19 C20 C21 -179.9(3) . . . . ? C19 C20 C21 N3 -0.3(5) . . . . ? C20 C19 C23 C22 0.3(5) . . . . ? C15 C19 C23 C22 -179.5(3) . . . . ? N3 C22 C23 C19 -1.0(6) . . . . ? C29 C24 C25 C26 0.4(5) . . . . ? C73 C24 C25 C26 178.4(3) . . . . ? C24 C25 C26 C27 -1.8(6) . . . . ? C25 C26 C27 C28 1.4(6) . . . . ? C25 C26 C27 O1 175.6(3) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? O1 C27 C28 C29 -174.2(3) . . . . ? C27 C28 C29 C24 -1.6(5) . . . . ? C25 C24 C29 C28 1.3(5) . . . . ? C73 C24 C29 C28 -176.6(3) . . . . ? C74 C31 C32 C83 1.6(7) . . . . ? N2 C33 C34 C37 -0.1(5) . . . . ? N2 C35 C36 C37 -0.6(5) . . . . ? C33 C34 C37 C36 3.1(5) . . . . ? C33 C34 C37 C38 -176.7(3) . . . . ? C35 C36 C37 C34 -2.8(5) . . . . ? C35 C36 C37 C38 177.0(3) . . . . ? C34 C37 C38 C39 151.1(3) . . . . ? C36 C37 C38 C39 -28.7(4) . . . . ? C34 C37 C38 C43 -30.3(5) . . . . ? C36 C37 C38 C43 149.9(3) . . . . ? C41 C12 C39 C38 -0.9(5) . . . . ? C43 C38 C39 C12 0.2(5) . . . . ? C37 C38 C39 C12 178.9(3) . . . . ? C39 C12 C41 C42 0.9(5) . . . . ? C39 C12 C41 N1 -179.0(3) . . . . ? C12 C41 C42 C43 -0.2(5) . . . . ? N1 C41 C42 C43 179.7(3) . . . . ? C41 C42 C43 C38 -0.5(5) . . . . ? C39 C38 C43 C42 0.5(5) . . . . ? C37 C38 C43 C42 -178.1(3) . . . . ? C25 C24 C73 O5 -4.8(5) . . . . ? C29 C24 C73 O5 173.1(3) . . . . ? C25 C24 C73 O4 174.9(3) . . . . ? C29 C24 C73 O4 -7.2(4) . . . . ? C32 C31 C74 O1 -176.8(4) . . . . ? C32 C31 C74 C81 -0.4(7) . . . . ? O1 C74 C81 C82 174.4(3) . . . . ? C31 C74 C81 C82 -1.8(6) . . . . ? C74 C81 C82 C83 2.8(6) . . . . ? C81 C82 C83 C32 -1.6(6) . . . . ? C81 C82 C83 C77 176.8(3) . . . . ? C31 C32 C83 C82 -0.6(6) . . . . ? C31 C32 C83 C77 -179.0(4) . . . . ? O3 C77 C83 C82 7.1(5) . . . . ? O2 C77 C83 C82 -169.1(3) . . . . ? O3 C77 C83 C32 -174.5(4) . . . . ? O2 C77 C83 C32 9.3(5) . . . . ? C17 C18 N1 C41 -144.8(3) . . . . ? C13 C18 N1 C41 35.3(4) . . . . ? C17 C18 N1 C9 52.7(4) . . . . ? C13 C18 N1 C9 -127.2(3) . . . . ? C42 C41 N1 C18 41.1(4) . . . . ? C12 C41 N1 C18 -138.9(3) . . . . ? C42 C41 N1 C9 -156.2(3) . . . . ? C12 C41 N1 C9 23.8(4) . . . . ? C10 C9 N1 C18 41.9(4) . . . . ? C8 C9 N1 C18 -142.1(3) . . . . ? C10 C9 N1 C41 -120.8(3) . . . . ? C8 C9 N1 C41 55.2(4) . . . . ? C34 C33 N2 C35 -3.3(5) . . . . ? C34 C33 N2 Co1 164.4(2) . . . . ? C36 C35 N2 C33 3.7(5) . . . . ? C36 C35 N2 Co1 -164.3(3) . . . . ? O4 Co1 N2 C33 0.5(3) . . . . ? O2 Co1 N2 C33 -106.7(2) 1_454 . . . ? N3 Co1 N2 C33 113.3(2) 2_645 . . . ? O3 Co1 N2 C33 -163.4(2) 1_454 . . . ? O4 Co1 N2 C35 167.8(2) . . . . ? O2 Co1 N2 C35 60.7(3) 1_454 . . . ? N3 Co1 N2 C35 -79.4(3) 2_645 . . . ? O3 Co1 N2 C35 3.9(2) 1_454 . . . ? C20 C21 N3 C22 -0.4(5) . . . . ? C20 C21 N3 Co1 -174.7(3) . . . 2_655 ? C23 C22 N3 C21 1.1(5) . . . . ? C23 C22 N3 Co1 175.2(3) . . . 2_655 ? C2 C1 N4 C4 0.2(7) . . . . ? C3 C4 N4 C1 0.3(7) . . . . ? C31 C74 O1 C27 -141.5(4) . . . . ? C81 C74 O1 C27 42.1(5) . . . . ? C28 C27 O1 C74 -134.4(4) . . . . ? C26 C27 O1 C74 51.2(5) . . . . ? O3 C77 O2 Co1 -9.4(4) . . . 1_656 ? C83 C77 O2 Co1 166.7(3) . . . 1_656 ? O2 C77 O3 Co1 8.0(3) . . . 1_656 ? C83 C77 O3 Co1 -168.2(3) . . . 1_656 ? O5 C73 O4 Co1 -28.2(6) . . . . ? C24 C73 O4 Co1 152.1(2) . . . . ? O2 Co1 O4 C73 142.0(3) 1_454 . . . ? N3 Co1 O4 C73 -89.5(3) 2_645 . . . ? N2 Co1 O4 C73 31.5(4) . . . . ? O3 Co1 O4 C73 176.6(3) 1_454 . . . ? 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 _platon_squeeze_void_content 1 0.500 0.000 0.000 10 1 ' ' 2 0.500 0.500 0.500 10 1 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.786 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 957215' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H32 F6 N4 O4 Zn' _chemical_formula_sum 'C50 H32 F6 N4 O4 Zn' _chemical_formula_weight 932.17 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pcca _symmetry_space_group_name_Hall '-p 2a 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' 'x+1/2, -y, -z+1/2' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' '-x-1/2, y, z-1/2' 'x, -y, z-1/2' _cell_length_a 19.407(7) _cell_length_b 13.628(5) _cell_length_c 16.307(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4313(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3547 _cell_measurement_theta_min 0.829 _cell_measurement_theta_max 0.862 _exptl_crystal_description solid _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.829 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26466 _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 24.40 _reflns_number_total 3547 _reflns_number_gt 2657 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1177P)^2^+1.0932P] 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 3547 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.2015 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.2500 0.0000 0.26236(4) 0.0374(3) Uani 1 2 d S . . F1 F 0.3177(2) -0.5489(2) 0.6760(2) 0.1049(13) Uani 1 1 d . . . F2 F 0.3711(2) -0.4850(2) 0.5749(3) 0.0893(11) Uani 1 1 d . . . F3 F 0.3105(2) -0.3956(2) 0.6532(2) 0.0978(12) Uani 1 1 d . . . O1 O 0.27688(17) -0.1352(2) 0.3013(2) 0.0544(8) Uani 1 1 d . . . O2 O 0.19039(18) -0.0823(2) 0.3746(2) 0.0679(9) Uani 1 1 d . . . N2 N 0.5000 0.2926(3) -0.2500 0.0444(12) Uani 1 2 d S . . N1 N 0.32347(17) 0.0426(2) 0.1751(2) 0.0418(8) Uani 1 1 d . . . N3 N 0.5000 0.9193(4) -0.2500 0.085(2) Uani 1 2 d S . . C1 C 0.3519(3) -0.0171(3) 0.1212(3) 0.0544(12) Uani 1 1 d . . . H1 H 0.3462 -0.0842 0.1290 0.065 Uiso 1 1 calc R . . C2 C 0.3894(3) 0.0130(3) 0.0544(3) 0.0524(12) Uani 1 1 d . . . H2 H 0.4082 -0.0329 0.0186 0.063 Uiso 1 1 calc R . . C5 C 0.3344(2) 0.1386(3) 0.1636(3) 0.0533(11) Uani 1 1 d . . . H5 H 0.3160 0.1825 0.2013 0.064 Uiso 1 1 calc R . . C4 C 0.3715(2) 0.1753(3) 0.0987(3) 0.0513(11) Uani 1 1 d . . . H4 H 0.3781 0.2426 0.0939 0.062 Uiso 1 1 calc R . . C3 C 0.3991(2) 0.1132(3) 0.0406(2) 0.0386(9) Uani 1 1 d . . . C6 C 0.4335(2) 0.1525(3) -0.0330(2) 0.0395(9) Uani 1 1 d . . . C7 C 0.42136(19) 0.1107(3) -0.1095(2) 0.0408(9) Uani 1 1 d . . . H7 H 0.3970 0.0521 -0.1129 0.049 Uiso 1 1 calc R . . C8 C 0.4449(2) 0.1549(3) -0.1804(2) 0.0415(9) Uani 1 1 d . . . H8 H 0.4364 0.1255 -0.2308 0.050 Uiso 1 1 calc R . . C9 C 0.4807(2) 0.2416(3) -0.1773(2) 0.0385(9) Uani 1 1 d . . . C10 C 0.4970(2) 0.2813(3) -0.1005(3) 0.0501(11) Uani 1 1 d . . . H10 H 0.5246 0.3370 -0.0970 0.060 Uiso 1 1 calc R . . C11 C 0.4724(2) 0.2381(3) -0.0303(2) 0.0491(10) Uani 1 1 d . . . H11 H 0.4819 0.2667 0.0202 0.059 Uiso 1 1 calc R . . C13 C 0.4474(2) 0.4486(3) -0.2131(3) 0.0512(11) Uani 1 1 d . . . H13 H 0.4114 0.4150 -0.1881 0.061 Uiso 1 1 calc R . . C12 C 0.5000 0.3972(4) -0.2500 0.0405(13) Uani 1 2 d S . . C14 C 0.4479(2) 0.5506(3) -0.2132(3) 0.0490(10) Uani 1 1 d . . . H14 H 0.4122 0.5844 -0.1877 0.059 Uiso 1 1 calc R . . C15 C 0.5000 0.6025(4) -0.2500 0.0399(13) Uani 1 2 d S . . C17 C 0.5374(2) 0.7658(3) -0.3058(3) 0.0562(11) Uani 1 1 d . . . H17 H 0.5638 0.7332 -0.3448 0.067 Uiso 1 1 calc R . . C18 C 0.5365(3) 0.8669(3) -0.3049(4) 0.0737(15) Uani 1 1 d . . . H18 H 0.5623 0.9004 -0.3439 0.088 Uiso 1 1 calc R . . C19 C 0.2347(2) -0.1443(3) 0.3599(3) 0.0497(11) Uani 1 1 d . . . C16 C 0.5000 0.7123(4) -0.2500 0.0424(14) Uani 1 2 d S . . C20 C 0.2380(2) -0.2369(3) 0.4103(3) 0.0437(10) Uani 1 1 d . . . C25 C 0.1942(3) -0.2484(3) 0.4763(3) 0.0606(13) Uani 1 1 d . . . H25 H 0.1625 -0.1995 0.4888 0.073 Uiso 1 1 calc R . . C24 C 0.1973(3) -0.3327(3) 0.5243(3) 0.0582(12) Uani 1 1 d . . . H24 H 0.1679 -0.3388 0.5691 0.070 Uiso 1 1 calc R . . C23 C 0.2425(2) -0.4066(3) 0.5071(3) 0.0423(10) Uani 1 1 d . . . C22 C 0.2857(2) -0.3947(3) 0.4400(3) 0.0537(11) Uani 1 1 d . . . H22 H 0.3163 -0.4446 0.4264 0.064 Uiso 1 1 calc R . . C26 C 0.2500 -0.5000 0.5606(4) 0.0510(16) Uani 1 2 d S . . C27 C 0.3123(4) -0.4837(3) 0.6160(4) 0.0752(18) Uani 1 1 d . . . C21 C 0.2843(2) -0.3100(3) 0.3926(3) 0.0540(12) Uani 1 1 d . . . H21 H 0.3147 -0.3028 0.3490 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0528(5) 0.0283(4) 0.0311(4) 0.000 0.000 -0.0037(3) F1 0.186(4) 0.0600(18) 0.069(2) 0.0167(16) -0.057(2) -0.027(2) F2 0.090(2) 0.074(2) 0.104(3) 0.0114(18) -0.038(2) -0.0159(17) F3 0.169(3) 0.0455(16) 0.078(2) -0.0101(15) -0.041(2) -0.0260(19) O1 0.0682(19) 0.0378(15) 0.0572(19) 0.0103(14) -0.0089(17) -0.0034(15) O2 0.080(2) 0.0398(16) 0.083(2) 0.0052(17) -0.0121(19) 0.0204(17) N2 0.065(3) 0.030(2) 0.038(3) 0.000 0.016(2) 0.000 N1 0.0582(19) 0.0310(17) 0.0361(18) 0.0012(14) 0.0040(16) -0.0052(15) N3 0.096(5) 0.038(3) 0.120(6) 0.000 -0.012(4) 0.000 C1 0.088(3) 0.0280(19) 0.048(3) 0.0033(18) 0.015(2) -0.005(2) C2 0.079(3) 0.0298(19) 0.048(3) 0.0007(18) 0.020(2) 0.000(2) C5 0.081(3) 0.032(2) 0.047(2) -0.0072(18) 0.024(2) -0.007(2) C4 0.078(3) 0.0298(19) 0.046(3) 0.0011(18) 0.016(2) -0.005(2) C3 0.051(2) 0.0301(18) 0.035(2) 0.0006(16) 0.0027(18) -0.0045(17) C6 0.049(2) 0.033(2) 0.036(2) 0.0030(17) 0.0031(18) -0.0008(17) C7 0.050(2) 0.0283(18) 0.045(2) -0.0069(16) 0.0038(18) -0.0035(17) C8 0.054(2) 0.036(2) 0.035(2) -0.0093(17) 0.0080(18) -0.0066(18) C9 0.048(2) 0.0339(19) 0.033(2) 0.0002(16) 0.0076(17) -0.0017(18) C10 0.066(3) 0.038(2) 0.046(2) -0.0005(19) 0.001(2) -0.020(2) C11 0.072(3) 0.043(2) 0.033(2) -0.0046(18) 0.003(2) -0.015(2) C13 0.060(3) 0.036(2) 0.057(3) 0.003(2) 0.023(2) 0.000(2) C12 0.057(3) 0.029(3) 0.035(3) 0.000 0.004(3) 0.000 C14 0.053(2) 0.038(2) 0.056(3) -0.003(2) 0.017(2) 0.0034(19) C15 0.049(3) 0.035(3) 0.036(3) 0.000 0.002(2) 0.000 C17 0.064(3) 0.034(2) 0.070(3) 0.006(2) 0.004(2) -0.008(2) C18 0.074(3) 0.046(3) 0.101(4) 0.022(3) 0.001(3) -0.007(3) C19 0.061(3) 0.033(2) 0.054(3) 0.004(2) -0.020(2) -0.004(2) C16 0.046(3) 0.031(3) 0.049(3) 0.000 -0.006(3) 0.000 C20 0.055(2) 0.0276(19) 0.049(2) 0.0022(18) -0.0092(19) 0.0007(17) C25 0.081(3) 0.039(2) 0.062(3) -0.002(2) 0.013(2) 0.022(2) C24 0.081(3) 0.042(2) 0.052(3) 0.002(2) 0.022(2) 0.004(2) C23 0.059(3) 0.026(2) 0.042(2) -0.0014(16) 0.0020(18) -0.0053(18) C22 0.064(3) 0.032(2) 0.065(3) 0.012(2) 0.019(2) 0.012(2) C26 0.080(4) 0.029(3) 0.045(4) 0.000 0.000 -0.001(3) C27 0.127(5) 0.041(3) 0.057(3) 0.003(2) -0.031(4) -0.018(3) C21 0.061(3) 0.037(2) 0.064(3) 0.014(2) 0.015(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 2.017(3) 2 ? Zn1 O1 2.017(3) . ? Zn1 N1 2.097(3) 2 ? Zn1 N1 2.097(3) . ? Zn1 O2 2.439(4) 2 ? Zn1 O2 2.439(4) . ? Zn1 C19 2.547(5) 2 ? F1 C27 1.326(6) . ? F2 C27 1.323(8) . ? F3 C27 1.345(6) . ? O1 C19 1.264(6) . ? O2 C19 1.229(5) . ? N2 C9 1.425(4) . ? N2 C9 1.425(4) 4_654 ? N2 C12 1.426(7) . ? N1 C1 1.319(6) . ? N1 C5 1.339(5) . ? N3 C18 1.347(6) . ? N3 C18 1.347(6) 4_654 ? C1 C2 1.372(6) . ? C1 H1 0.9300 . ? C2 C3 1.397(5) . ? C2 H2 0.9300 . ? C5 C4 1.375(6) . ? C5 H5 0.9300 . ? C4 C3 1.378(5) . ? C4 H4 0.9300 . ? C3 C6 1.475(5) . ? C6 C11 1.389(5) . ? C6 C7 1.390(5) . ? C7 C8 1.381(5) . ? C7 H7 0.9300 . ? C8 C9 1.371(5) . ? C8 H8 0.9300 . ? C9 C10 1.401(6) . ? C10 C11 1.373(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C13 C12 1.376(5) . ? C13 C14 1.390(6) . ? C13 H13 0.9300 . ? C12 C13 1.376(5) 4_654 ? C14 C15 1.371(5) . ? C14 H14 0.9300 . ? C15 C14 1.371(5) 4_654 ? C15 C16 1.496(8) . ? C17 C16 1.373(5) . ? C17 C18 1.378(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.508(6) . ? C16 C17 1.373(5) 4_654 ? C20 C21 1.372(6) . ? C20 C25 1.379(6) . ? C25 C24 1.391(6) . ? C25 H25 0.9300 . ? C24 C23 1.364(6) . ? C24 H24 0.9300 . ? C23 C22 1.388(6) . ? C23 C26 1.551(6) . ? C22 C21 1.389(6) . ? C22 H22 0.9300 . ? C26 C27 1.526(7) 2_545 ? C26 C27 1.526(7) . ? C26 C23 1.551(6) 2_545 ? C21 H21 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 O1 Zn1 O1 143.3(2) 2 . ? O1 Zn1 N1 106.89(13) 2 2 ? O1 Zn1 N1 97.86(12) . 2 ? O1 Zn1 N1 97.86(12) 2 . ? O1 Zn1 N1 106.89(13) . . ? N1 Zn1 N1 94.49(18) 2 . ? O1 Zn1 O2 57.75(12) 2 2 ? O1 Zn1 O2 93.50(12) . 2 ? N1 Zn1 O2 163.63(12) 2 2 ? N1 Zn1 O2 93.42(12) . 2 ? O1 Zn1 O2 93.50(12) 2 . ? O1 Zn1 O2 57.75(12) . . ? N1 Zn1 O2 93.42(12) 2 . ? N1 Zn1 O2 163.63(12) . . ? O2 Zn1 O2 82.71(16) 2 . ? O1 Zn1 C19 29.34(14) 2 2 ? O1 Zn1 C19 118.59(15) . 2 ? N1 Zn1 C19 135.81(14) 2 2 ? N1 Zn1 C19 97.51(13) . 2 ? O2 Zn1 C19 28.44(13) 2 2 ? O2 Zn1 C19 86.67(13) . 2 ? C19 O1 Zn1 99.2(3) . . ? C19 O2 Zn1 80.6(3) . . ? C9 N2 C9 121.6(4) . 4_654 ? C9 N2 C12 119.2(2) . . ? C9 N2 C12 119.2(2) 4_654 . ? C1 N1 C5 116.3(4) . . ? C1 N1 Zn1 124.5(3) . . ? C5 N1 Zn1 118.2(3) . . ? C18 N3 C18 115.9(6) . 4_654 ? N1 C1 C2 124.6(4) . . ? N1 C1 H1 117.7 . . ? C2 C1 H1 117.7 . . ? C1 C2 C3 119.4(4) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? N1 C5 C4 123.1(4) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C3 C2 115.9(4) . . ? C4 C3 C6 120.8(3) . . ? C2 C3 C6 123.2(4) . . ? C11 C6 C7 117.7(4) . . ? C11 C6 C3 121.6(4) . . ? C7 C6 C3 120.3(3) . . ? C8 C7 C6 121.1(3) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 118.7(4) . . ? C8 C9 N2 121.5(3) . . ? C10 C9 N2 119.7(3) . . ? C11 C10 C9 120.0(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C6 121.5(4) . . ? C10 C11 H11 119.2 . . ? C6 C11 H11 119.2 . . ? C12 C13 C14 120.2(4) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C12 C13 118.8(5) . 4_654 ? C13 C12 N2 120.6(2) . . ? C13 C12 N2 120.6(2) 4_654 . ? C15 C14 C13 121.4(4) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C14 118.0(5) . 4_654 ? C14 C15 C16 121.0(3) . . ? C14 C15 C16 121.0(3) 4_654 . ? C16 C17 C18 121.1(5) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? N3 C18 C17 122.9(5) . . ? N3 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? O2 C19 O1 122.2(4) . . ? O2 C19 C20 119.9(5) . . ? O1 C19 C20 117.9(4) . . ? C17 C16 C17 115.9(5) 4_654 . ? C17 C16 C15 122.1(3) 4_654 . ? C17 C16 C15 122.1(3) . . ? C21 C20 C25 119.0(4) . . ? C21 C20 C19 121.3(4) . . ? C25 C20 C19 119.7(4) . . ? C20 C25 C24 120.4(4) . . ? C20 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C23 C24 C25 121.4(4) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C24 C23 C22 117.7(4) . . ? C24 C23 C26 123.4(4) . . ? C22 C23 C26 118.8(4) . . ? C23 C22 C21 121.6(4) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C27 C26 C27 107.3(7) 2_545 . ? C27 C26 C23 112.2(3) 2_545 . ? C27 C26 C23 106.8(2) . . ? C27 C26 C23 106.8(2) 2_545 2_545 ? C27 C26 C23 112.2(3) . 2_545 ? C23 C26 C23 111.5(5) . 2_545 ? F2 C27 F1 107.3(5) . . ? F2 C27 F3 105.2(5) . . ? F1 C27 F3 105.5(4) . . ? F2 C27 C26 112.4(5) . . ? F1 C27 C26 113.7(5) . . ? F3 C27 C26 112.2(5) . . ? C20 C21 C22 119.9(4) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? 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 O1 Zn1 O1 C19 41.2(2) 2 . . . ? N1 Zn1 O1 C19 -91.4(3) 2 . . . ? N1 Zn1 O1 C19 171.5(3) . . . . ? O2 Zn1 O1 C19 76.8(3) 2 . . . ? O2 Zn1 O1 C19 -2.3(2) . . . . ? C19 Zn1 O1 C19 62.8(3) 2 . . . ? O1 Zn1 O2 C19 -153.3(3) 2 . . . ? O1 Zn1 O2 C19 2.3(2) . . . . ? N1 Zn1 O2 C19 99.5(3) 2 . . . ? N1 Zn1 O2 C19 -19.3(6) . . . . ? O2 Zn1 O2 C19 -96.5(3) 2 . . . ? C19 Zn1 O2 C19 -124.8(3) 2 . . . ? O1 Zn1 N1 C1 -170.0(4) 2 . . . ? O1 Zn1 N1 C1 37.4(4) . . . . ? N1 Zn1 N1 C1 -62.2(3) 2 . . . ? O2 Zn1 N1 C1 132.1(4) 2 . . . ? O2 Zn1 N1 C1 56.4(6) . . . . ? C19 Zn1 N1 C1 160.4(4) 2 . . . ? O1 Zn1 N1 C5 -1.5(3) 2 . . . ? O1 Zn1 N1 C5 -154.1(3) . . . . ? N1 Zn1 N1 C5 106.3(4) 2 . . . ? O2 Zn1 N1 C5 -59.4(3) 2 . . . ? O2 Zn1 N1 C5 -135.1(4) . . . . ? C19 Zn1 N1 C5 -31.1(4) 2 . . . ? C5 N1 C1 C2 -2.0(7) . . . . ? Zn1 N1 C1 C2 166.7(4) . . . . ? N1 C1 C2 C3 -0.1(8) . . . . ? C1 N1 C5 C4 1.6(7) . . . . ? Zn1 N1 C5 C4 -167.9(4) . . . . ? N1 C5 C4 C3 0.8(7) . . . . ? C5 C4 C3 C2 -2.8(7) . . . . ? C5 C4 C3 C6 174.4(4) . . . . ? C1 C2 C3 C4 2.4(7) . . . . ? C1 C2 C3 C6 -174.7(4) . . . . ? C4 C3 C6 C11 35.5(6) . . . . ? C2 C3 C6 C11 -147.5(5) . . . . ? C4 C3 C6 C7 -137.1(4) . . . . ? C2 C3 C6 C7 39.9(6) . . . . ? C11 C6 C7 C8 -2.5(6) . . . . ? C3 C6 C7 C8 170.5(4) . . . . ? C6 C7 C8 C9 -0.3(6) . . . . ? C7 C8 C9 C10 4.3(6) . . . . ? C7 C8 C9 N2 -174.3(3) . . . . ? C9 N2 C9 C8 -35.4(3) 4_654 . . . ? C12 N2 C9 C8 144.6(3) . . . . ? C9 N2 C9 C10 146.0(4) 4_654 . . . ? C12 N2 C9 C10 -34.0(4) . . . . ? C8 C9 C10 C11 -5.5(6) . . . . ? N2 C9 C10 C11 173.1(4) . . . . ? C9 C10 C11 C6 2.8(7) . . . . ? C7 C6 C11 C10 1.2(6) . . . . ? C3 C6 C11 C10 -171.6(4) . . . . ? C14 C13 C12 C13 -0.2(3) . . . 4_654 ? C14 C13 C12 N2 179.8(3) . . . . ? C9 N2 C12 C13 -42.0(3) . . . . ? C9 N2 C12 C13 138.0(3) 4_654 . . . ? C9 N2 C12 C13 138.0(3) . . . 4_654 ? C9 N2 C12 C13 -42.0(3) 4_654 . . 4_654 ? C12 C13 C14 C15 0.4(6) . . . . ? C13 C14 C15 C14 -0.2(3) . . . 4_654 ? C13 C14 C15 C16 179.8(3) . . . . ? C18 N3 C18 C17 -0.2(4) 4_654 . . . ? C16 C17 C18 N3 0.4(8) . . . . ? Zn1 O2 C19 O1 -3.7(4) . . . . ? Zn1 O2 C19 C20 178.9(4) . . . . ? Zn1 O1 C19 O2 4.5(5) . . . . ? Zn1 O1 C19 C20 -178.0(3) . . . . ? C18 C17 C16 C17 -0.2(4) . . . 4_654 ? C18 C17 C16 C15 179.8(4) . . . . ? C14 C15 C16 C17 20.7(3) . . . 4_654 ? C14 C15 C16 C17 -159.3(3) 4_654 . . 4_654 ? C14 C15 C16 C17 -159.3(3) . . . . ? C14 C15 C16 C17 20.7(3) 4_654 . . . ? O2 C19 C20 C21 176.4(4) . . . . ? O1 C19 C20 C21 -1.1(6) . . . . ? O2 C19 C20 C25 -4.5(6) . . . . ? O1 C19 C20 C25 178.0(4) . . . . ? C21 C20 C25 C24 0.2(7) . . . . ? C19 C20 C25 C24 -179.0(4) . . . . ? C20 C25 C24 C23 -1.0(8) . . . . ? C25 C24 C23 C22 0.2(7) . . . . ? C25 C24 C23 C26 177.4(4) . . . . ? C24 C23 C22 C21 1.3(7) . . . . ? C26 C23 C22 C21 -176.1(4) . . . . ? C24 C23 C26 C27 18.7(6) . . . 2_545 ? C22 C23 C26 C27 -164.2(4) . . . 2_545 ? C24 C23 C26 C27 -98.7(5) . . . . ? C22 C23 C26 C27 78.5(6) . . . . ? C24 C23 C26 C23 138.4(5) . . . 2_545 ? C22 C23 C26 C23 -44.5(3) . . . 2_545 ? C27 C26 C27 F2 169.4(5) 2_545 . . . ? C23 C26 C27 F2 -70.0(5) . . . . ? C23 C26 C27 F2 52.4(5) 2_545 . . . ? C27 C26 C27 F1 47.4(4) 2_545 . . . ? C23 C26 C27 F1 167.9(5) . . . . ? C23 C26 C27 F1 -69.6(7) 2_545 . . . ? C27 C26 C27 F3 -72.2(5) 2_545 . . . ? C23 C26 C27 F3 48.3(6) . . . . ? C23 C26 C27 F3 170.8(4) 2_545 . . . ? C25 C20 C21 C22 1.3(7) . . . . ? C19 C20 C21 C22 -179.6(4) . . . . ? C23 C22 C21 C20 -2.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.636 _refine_diff_density_min -1.318 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 957216' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H32 Co F6 N4 O4' _chemical_formula_sum 'C50 H32 Co F6 N4 O4' _chemical_formula_weight 925.73 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pcca _symmetry_space_group_name_Hall '-p 2a 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 19.414(4) _cell_length_b 13.605(2) _cell_length_c 16.216(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4283.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3652 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 24.71 _exptl_crystal_description solid _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1892 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 28974 _diffrn_reflns_av_R_equivalents 0.1252 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 24.71 _reflns_number_total 3652 _reflns_number_gt 2496 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0629P)^2^+0.3528P] 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 3652 _refine_ls_number_parameters 297 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.046 _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 O2 O 0.78227(10) 0.85799(15) 0.20472(13) 0.0501(5) Uani 1 1 d . . . Co1 Co 0.7500 1.0000 0.23280(3) 0.03840(19) Uani 1 2 d SU . . O1 O 0.69790(11) 0.91812(15) 0.13132(12) 0.0531(5) Uani 1 1 d U . . N2 N 0.5000 0.7126(2) 0.7500 0.0459(9) Uani 1 2 d S . . C11 C 0.57797(14) 0.8938(2) 0.60813(17) 0.0417(7) Uani 1 1 d . . . H11 H 0.6021 0.9527 0.6112 0.050 Uiso 1 1 calc R . . N1 N 0.67831(12) 0.95514(18) 0.32208(14) 0.0436(6) Uani 1 1 d . . . F1 F 0.68775(15) 0.39767(16) -0.15399(14) 0.0986(8) Uani 1 1 d . . . C8 C 0.50188(15) 0.7235(2) 0.60055(18) 0.0502(8) Uani 1 1 d . . . H8 H 0.4743 0.6677 0.5976 0.060 Uiso 1 1 calc R . . C6 C 0.56599(14) 0.8511(2) 0.53147(17) 0.0409(7) Uani 1 1 d . . . C10 C 0.55466(14) 0.8500(2) 0.67957(17) 0.0423(7) Uani 1 1 d . . . H10 H 0.5636 0.8796 0.7302 0.051 Uiso 1 1 calc R . . C9 C 0.51833(14) 0.7633(2) 0.67700(17) 0.0398(7) Uani 1 1 d . . . C20 C 0.74172(14) 0.7618(2) 0.09253(18) 0.0415(7) Uani 1 1 d . . . C23 C 0.74418(15) 0.5933(2) -0.00691(18) 0.0457(7) Uani 1 1 d . . . C1 C 0.66666(17) 0.8602(2) 0.33594(19) 0.0553(9) Uani 1 1 d . . . H1 H 0.6853 0.8149 0.2992 0.066 Uiso 1 1 calc R . . C21 C 0.69842(18) 0.7524(2) 0.0258(2) 0.0591(9) Uani 1 1 d . . . H21 H 0.6674 0.8026 0.0139 0.071 Uiso 1 1 calc R . . F3 F 0.68269(15) 0.55269(16) -0.17651(13) 0.1022(9) Uani 1 1 d . . . C4 C 0.64898(17) 1.0168(2) 0.3753(2) 0.0533(8) Uani 1 1 d . . . H4 H 0.6551 1.0839 0.3667 0.064 Uiso 1 1 calc R . . C3 C 0.60088(14) 0.8887(2) 0.45754(17) 0.0410(7) Uani 1 1 d . . . C15 C 0.5000 0.4017(3) 0.7500 0.0422(10) Uani 1 2 d S . . C24 C 0.78737(18) 0.6027(2) 0.0599(2) 0.0603(9) Uani 1 1 d . . . H24 H 0.8177 0.5519 0.0725 0.072 Uiso 1 1 calc R . . C22 C 0.70017(19) 0.6702(2) -0.0237(2) 0.0606(9) Uani 1 1 d . . . H22 H 0.6711 0.6664 -0.0692 0.073 Uiso 1 1 calc R . . C7 C 0.52598(17) 0.7659(2) 0.52943(18) 0.0519(8) Uani 1 1 d . . . H7 H 0.5155 0.7373 0.4789 0.062 Uiso 1 1 calc R . . C12 C 0.5000 0.6080(3) 0.7500 0.0408(10) Uani 1 2 d S . . C27 C 0.6873(3) 0.4857(3) -0.1165(2) 0.0750(12) Uani 1 1 d . . . C16 C 0.5000 0.2930(3) 0.7500 0.0441(10) Uani 1 2 d S . . C5 C 0.61043(18) 0.9882(2) 0.44186(19) 0.0537(8) Uani 1 1 d . . . H5 H 0.5908 1.0351 0.4763 0.064 Uiso 1 1 calc R . . N3 N 0.5000 0.0855(3) 0.7500 0.0783(13) Uani 1 2 d S . . C17 C 0.46084(17) 0.2383(2) 0.8048(2) 0.0585(9) Uani 1 1 d . . . H17 H 0.4332 0.2700 0.8434 0.070 Uiso 1 1 calc R . . C26 C 0.7500 0.5000 -0.0610(3) 0.0515(11) Uani 1 2 d S . . C19 C 0.74055(15) 0.8513(2) 0.14541(19) 0.0433(7) Uani 1 1 d . . . C2 C 0.62901(17) 0.8250(2) 0.40091(19) 0.0537(8) Uani 1 1 d . . . H2 H 0.6224 0.7577 0.4068 0.064 Uiso 1 1 calc R . . C13 C 0.44819(16) 0.5561(2) 0.7875(2) 0.0549(9) Uani 1 1 d . . . H13 H 0.4123 0.5895 0.8132 0.066 Uiso 1 1 calc R . . F2 F 0.62887(13) 0.48930(16) -0.07436(16) 0.0893(8) Uani 1 1 d . . . C18 C 0.4628(2) 0.1373(3) 0.8023(3) 0.0758(11) Uani 1 1 d . . . H18 H 0.4359 0.1031 0.8401 0.091 Uiso 1 1 calc R . . C25 C 0.78655(17) 0.6859(2) 0.1087(2) 0.0593(9) Uani 1 1 d . . . H25 H 0.8167 0.6907 0.1530 0.071 Uiso 1 1 calc R . . C14 C 0.44873(16) 0.4549(2) 0.7875(2) 0.0558(9) Uani 1 1 d . . . H14 H 0.4132 0.4215 0.8138 0.067 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0489(11) 0.0442(13) 0.0571(13) -0.0088(11) -0.0012(11) 0.0005(10) Co1 0.0468(3) 0.0319(3) 0.0365(3) 0.000 0.000 -0.0017(3) O1 0.0697(14) 0.0384(13) 0.0513(12) -0.0096(9) -0.0051(10) 0.0087(11) N2 0.067(2) 0.030(2) 0.041(2) 0.000 0.0106(16) 0.000 C11 0.0471(16) 0.0306(16) 0.0474(18) -0.0046(14) 0.0062(13) -0.0033(13) N1 0.0549(14) 0.0349(15) 0.0412(14) -0.0007(12) 0.0044(11) -0.0042(12) F1 0.170(2) 0.0433(13) 0.0825(15) -0.0088(11) -0.0420(15) -0.0190(14) C8 0.0609(19) 0.0443(19) 0.0455(19) 0.0000(16) 0.0034(14) -0.0187(15) C6 0.0493(16) 0.0347(17) 0.0387(17) 0.0018(13) 0.0027(13) -0.0013(13) C10 0.0505(17) 0.0371(18) 0.0391(17) -0.0052(13) 0.0070(13) -0.0001(14) C9 0.0456(15) 0.0367(17) 0.0370(16) 0.0002(14) 0.0049(13) -0.0007(13) C20 0.0456(16) 0.0339(17) 0.0450(17) -0.0013(13) 0.0029(14) 0.0009(13) C23 0.0599(18) 0.0317(17) 0.0456(17) 0.0015(13) -0.0024(15) -0.0063(15) C1 0.079(2) 0.035(2) 0.0510(19) -0.0081(16) 0.0205(17) -0.0044(16) C21 0.079(2) 0.0377(19) 0.061(2) -0.0016(17) -0.0111(18) 0.0179(17) F3 0.183(3) 0.0537(14) 0.0701(15) 0.0135(12) -0.0533(15) -0.0177(15) C4 0.077(2) 0.0315(18) 0.0511(19) 0.0004(15) 0.0150(17) -0.0058(15) C3 0.0494(16) 0.0352(17) 0.0383(16) 0.0021(13) 0.0015(13) -0.0032(13) C15 0.049(2) 0.036(2) 0.041(2) 0.000 -0.0011(19) 0.000 C24 0.068(2) 0.0389(19) 0.074(2) -0.0137(18) -0.0198(19) 0.0138(17) C22 0.086(2) 0.042(2) 0.054(2) -0.0034(17) -0.0262(18) 0.0119(18) C7 0.070(2) 0.048(2) 0.0373(17) -0.0050(15) -0.0010(15) -0.0161(17) C12 0.051(2) 0.036(2) 0.036(2) 0.000 0.0055(18) 0.000 C27 0.122(4) 0.041(2) 0.062(2) 0.0047(19) -0.031(2) -0.019(2) C16 0.046(2) 0.036(3) 0.050(3) 0.000 -0.0030(19) 0.000 C5 0.076(2) 0.0341(19) 0.0511(19) -0.0072(15) 0.0173(17) 0.0000(16) N3 0.081(3) 0.036(3) 0.118(4) 0.000 -0.012(3) 0.000 C17 0.065(2) 0.043(2) 0.068(2) 0.0040(17) 0.0023(18) -0.0020(17) C26 0.075(3) 0.031(2) 0.049(3) 0.000 0.000 -0.005(2) C19 0.0441(17) 0.0377(18) 0.0480(18) 0.0004(14) 0.0105(14) 0.0012(14) C2 0.078(2) 0.0324(17) 0.0512(19) 0.0002(15) 0.0183(17) -0.0075(16) C13 0.057(2) 0.038(2) 0.069(2) 0.0003(17) 0.0266(16) 0.0058(15) F2 0.0885(16) 0.0710(16) 0.108(2) 0.0074(13) -0.0354(15) -0.0158(13) C18 0.077(3) 0.047(2) 0.103(3) 0.017(2) -0.003(2) -0.011(2) C25 0.063(2) 0.044(2) 0.071(2) -0.0149(18) -0.0246(18) 0.0133(17) C14 0.057(2) 0.045(2) 0.066(2) 0.0051(17) 0.0186(16) -0.0039(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C19 1.261(4) . ? O2 Co1 2.082(2) . ? Co1 O2 2.081(2) 2_675 ? Co1 N1 2.099(2) 2_675 ? Co1 N1 2.099(2) . ? Co1 O1 2.230(2) . ? Co1 O1 2.230(2) 2_675 ? Co1 C19 2.477(3) 2_675 ? O1 C19 1.251(3) . ? N2 C9 1.416(3) 3_656 ? N2 C9 1.416(3) . ? N2 C12 1.422(5) . ? C11 C10 1.379(4) . ? C11 C6 1.391(4) . ? C11 H11 0.9300 . ? N1 C1 1.330(4) . ? N1 C4 1.332(4) . ? F1 C27 1.343(4) . ? C8 C7 1.372(4) . ? C8 C9 1.390(4) . ? C8 H8 0.9300 . ? C6 C7 1.395(4) . ? C6 C3 1.469(4) . ? C10 C9 1.376(4) . ? C10 H10 0.9300 . ? C20 C25 1.376(4) . ? C20 C21 1.376(4) . ? C20 C19 1.489(4) . ? C23 C24 1.376(4) . ? C23 C22 1.377(4) . ? C23 C26 1.547(4) . ? C1 C2 1.369(4) . ? C1 H1 0.9300 . ? C21 C22 1.378(4) . ? C21 H21 0.9300 . ? F3 C27 1.336(4) . ? C4 C5 1.370(4) . ? C4 H4 0.9300 . ? C3 C2 1.376(4) . ? C3 C5 1.390(4) . ? C15 C14 1.373(4) 3_656 ? C15 C14 1.373(4) . ? C15 C16 1.478(6) . ? C24 C25 1.381(4) . ? C24 H24 0.9300 . ? C22 H22 0.9300 . ? C7 H7 0.9300 . ? C12 C13 1.372(4) 3_656 ? C12 C13 1.372(4) . ? C27 F2 1.325(5) . ? C27 C26 1.527(5) . ? C16 C17 1.387(4) . ? C16 C17 1.387(4) 3_656 ? C5 H5 0.9300 . ? N3 C18 1.318(4) 3_656 ? N3 C18 1.318(4) . ? C17 C18 1.375(5) . ? C17 H17 0.9300 . ? C26 C27 1.527(5) 2_665 ? C26 C23 1.547(4) 2_665 ? C2 H2 0.9300 . ? C13 C14 1.376(4) . ? C13 H13 0.9300 . ? C18 H18 0.9300 . ? C25 H25 0.9300 . ? C14 H14 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 C19 O2 Co1 92.33(18) . . ? O2 Co1 O2 154.73(12) 2_675 . ? O2 Co1 N1 94.62(9) 2_675 2_675 ? O2 Co1 N1 102.78(9) . 2_675 ? O2 Co1 N1 102.78(9) 2_675 . ? O2 Co1 N1 94.62(9) . . ? N1 Co1 N1 92.78(13) 2_675 . ? O2 Co1 O1 99.54(8) 2_675 . ? O2 Co1 O1 60.75(8) . . ? N1 Co1 O1 162.76(9) 2_675 . ? N1 Co1 O1 93.61(9) . . ? O2 Co1 O1 60.75(8) 2_675 2_675 ? O2 Co1 O1 99.54(8) . 2_675 ? N1 Co1 O1 93.61(9) 2_675 2_675 ? N1 Co1 O1 162.77(9) . 2_675 ? O1 Co1 O1 84.88(11) . 2_675 ? O2 Co1 C19 30.57(9) 2_675 2_675 ? O2 Co1 C19 127.64(10) . 2_675 ? N1 Co1 C19 96.20(9) 2_675 2_675 ? N1 Co1 C19 132.94(10) . 2_675 ? O1 Co1 C19 91.11(9) . 2_675 ? O1 Co1 C19 30.24(8) 2_675 2_675 ? C19 O1 Co1 85.87(18) . . ? C9 N2 C9 121.7(3) 3_656 . ? C9 N2 C12 119.17(16) 3_656 . ? C9 N2 C12 119.17(16) . . ? C10 C11 C6 121.1(3) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C1 N1 C4 115.5(3) . . ? C1 N1 Co1 120.8(2) . . ? C4 N1 Co1 123.2(2) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C11 C6 C7 117.4(3) . . ? C11 C6 C3 120.4(3) . . ? C7 C6 C3 121.8(3) . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C9 C8 118.6(3) . . ? C10 C9 N2 121.4(2) . . ? C8 C9 N2 119.9(3) . . ? C25 C20 C21 117.8(3) . . ? C25 C20 C19 120.9(3) . . ? C21 C20 C19 121.3(3) . . ? C24 C23 C22 117.6(3) . . ? C24 C23 C26 118.5(3) . . ? C22 C23 C26 123.8(3) . . ? N1 C1 C2 124.1(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C20 C21 C22 121.2(3) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? N1 C4 C5 124.4(3) . . ? N1 C4 H4 117.8 . . ? C5 C4 H4 117.8 . . ? C2 C3 C5 116.0(3) . . ? C2 C3 C6 120.6(3) . . ? C5 C3 C6 123.4(3) . . ? C14 C15 C14 116.3(4) 3_656 . ? C14 C15 C16 121.8(2) 3_656 . ? C14 C15 C16 121.8(2) . . ? C23 C24 C25 121.3(3) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C21 C22 C23 121.1(3) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C8 C7 C6 121.3(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C13 C12 C13 117.9(4) 3_656 . ? C13 C12 N2 121.0(2) 3_656 . ? C13 C12 N2 121.0(2) . . ? F2 C27 F3 107.1(4) . . ? F2 C27 F1 105.8(3) . . ? F3 C27 F1 106.2(3) . . ? F2 C27 C26 112.0(3) . . ? F3 C27 C26 113.3(3) . . ? F1 C27 C26 112.0(3) . . ? C17 C16 C17 115.1(4) . 3_656 ? C17 C16 C15 122.5(2) . . ? C17 C16 C15 122.5(2) 3_656 . ? C4 C5 C3 119.6(3) . . ? C4 C5 H5 120.2 . . ? C3 C5 H5 120.2 . . ? C18 N3 C18 115.4(5) 3_656 . ? C18 C17 C16 120.2(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C27 C26 C27 107.8(5) 2_665 . ? C27 C26 C23 106.73(18) 2_665 . ? C27 C26 C23 112.4(2) . . ? C27 C26 C23 112.4(2) 2_665 2_665 ? C27 C26 C23 106.73(18) . 2_665 ? C23 C26 C23 110.9(4) . 2_665 ? O1 C19 O2 120.8(3) . . ? O1 C19 C20 119.9(3) . . ? O2 C19 C20 119.3(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C12 C13 C14 120.7(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? N3 C18 C17 124.6(4) . . ? N3 C18 H18 117.7 . . ? C17 C18 H18 117.7 . . ? C20 C25 C24 120.9(3) . . ? C20 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C15 C14 C13 122.2(3) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.327 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 957217'