# 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H Co N O' _chemical_formula_weight 101.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z+1/2' 'y, -x, z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z-1/2' '-y, x, -z-1/2' _cell_length_a 15.0103(8) _cell_length_b 15.0103(8) _cell_length_c 10.0791(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2270.9(3) _cell_formula_units_Z 29 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1421 _exptl_absorpt_coefficient_mu 5.203 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25747 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2120 _reflns_number_gt 1575 _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^)+(0.1032P)^2^+4.5275P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2120 _refine_ls_number_parameters 204 _refine_ls_number_restraints 288 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2387 _refine_ls_wR_factor_gt 0.2106 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.282 _refine_ls_shift/su_max 2.553 _refine_ls_shift/su_mean 0.088 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.33643(2) -0.066582(17) 0.0000 0.07610(10) Uani 1 2 d S . . N1 N 0.26325(13) -0.18205(14) 0.0000 0.0904(7) Uani 1 2 d S . . N2 N 0.31602(11) 0.06735(10) 0.0000 0.0699(5) Uani 1 2 d S . . N3 N 0.34195(11) 0.21091(11) 0.0000 0.0908(7) Uani 1 2 d S . . O1 O 0.30482(8) -0.05119(8) 0.24955(13) 0.0991(4) Uani 1 1 d . . . O2 O 0.42433(8) -0.09361(7) 0.14536(9) 0.0828(3) Uani 1 1 d . . . O3 O 0.0000 0.0000 0.2500 0.61(2) Uani 0.50 4 d SP . . O4 O 0.1334(2) 0.9973(3) 0.3682(5) 0.385(3) Uani 1 1 d . . . C1 C 0.2106(2) -0.2103(2) 0.0957(3) 0.1075(10) Uani 0.50 1 d PU . . H1 H 0.1964 -0.1686 0.1675 0.129 Uiso 0.50 1 calc PR . . C3 C 0.7054(2) -0.1738(2) 0.3981(3) 0.1160(9) Uani 0.60 1 d PU . . C4 C 0.64555(16) -0.18631(14) 0.5000 0.0805(6) Uani 1 2 d SU . . C5 C 0.55571(15) -0.14831(12) 0.5000 0.0711(6) Uani 1 2 d SU . . C6 C 0.51152(10) -0.13041(8) 0.38179(13) 0.0691(4) Uani 1 1 d U . . H6 H 0.5399 -0.1421 0.3016 0.083 Uiso 1 1 calc R . . C7 C 0.42673(10) -0.09576(8) 0.38112(12) 0.0636(4) Uani 1 1 d U . . C8 C 0.38296(15) -0.07772(11) 0.5000 0.0666(6) Uani 1 2 d SU . . H8 H 0.3257 -0.0541 0.5000 0.080 Uiso 1 2 calc SR . . C9 C 0.38140(10) -0.07775(9) 0.24993(15) 0.0731(4) Uani 1 1 d U . . C10 C 0.23752(17) 0.11230(19) 0.0000 0.1375(10) Uani 1 2 d SU . . H10 H 0.1786 0.0841 0.0000 0.165 Uiso 1 2 calc SR . . C11 C 0.25313(18) 0.19865(18) -0.0329(6) 0.1235(9) Uani 0.50 1 d PU . . H11 H 0.2169 0.2363 -0.0913 0.148 Uiso 0.50 1 calc PR . . C12 C 0.37640(14) 0.12899(13) 0.0000 0.0856(7) Uani 1 2 d SU . . H12 H 0.4373 0.1174 0.0000 0.103 Uiso 1 2 calc SR . . C13 C 0.38829(17) 0.29312(15) 0.0000 0.1380(8) Uani 1 2 d SU . . C14 C 0.3420(2) 0.36970(17) 0.0000 0.1904(9) Uani 1 2 d SU . . H14 H 0.2767 0.3681 0.0000 0.228 Uiso 1 2 calc SR . . C15 C 0.3893(2) 0.4497(2) -0.0518(6) 0.1658(10) Uani 0.50 1 d PU . . H15 H 0.3608 0.4958 -0.1060 0.199 Uiso 0.50 1 calc PR . . C16 C 0.4760(2) 0.45662(16) 0.0000 0.1747(9) Uani 1 2 d SU . . C17 C 0.5201(2) 0.37798(18) 0.0000 0.1946(10) Uani 1 2 d SU . . H17 H 0.5854 0.3792 0.0000 0.234 Uiso 1 2 calc SR . . C18 C 0.4761(2) 0.29818(18) 0.0465(6) 0.1334(9) Uani 0.50 1 d PU . . H18 H 0.5048 0.2524 0.1013 0.160 Uiso 0.50 1 calc PR . . O5 O 0.1439(14) 0.9472(6) 0.0000 0.928(17) Uani 1 2 d S . . C2 C 0.6707(3) -0.2475(2) 0.4007(4) 0.0775(9) Uani 0.40 1 d PU . . C19 C 0.2827(2) -0.2445(3) 0.0964(4) 0.1000(11) Uani 0.50 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.1192(2) 0.05499(13) 0.05414(14) 0.000 0.000 0.00031(14) N1 0.0941(12) 0.1067(13) 0.0705(10) 0.000 0.000 -0.0249(10) N2 0.0654(9) 0.0655(9) 0.0789(10) 0.000 0.000 0.0032(7) N3 0.0635(9) 0.0553(8) 0.1537(18) 0.000 0.000 0.0101(8) O1 0.0965(7) 0.1193(8) 0.0815(7) 0.0067(7) -0.0115(6) 0.0079(6) O2 0.1156(7) 0.0821(6) 0.0506(5) 0.0005(5) -0.0041(5) 0.0019(5) O3 0.184(6) 0.184(6) 1.45(6) 0.000 0.000 0.000 O4 0.264(3) 0.360(4) 0.531(7) 0.072(4) 0.050(4) 0.032(3) C1 0.1139(17) 0.1178(18) 0.0907(16) -0.0494(15) 0.0511(15) -0.0566(15) C3 0.1359(17) 0.1334(16) 0.0786(14) 0.0390(14) 0.0316(14) 0.0496(15) C4 0.1050(13) 0.0751(11) 0.0612(10) 0.000 0.000 0.0194(10) C5 0.1014(12) 0.0568(9) 0.0551(9) 0.000 0.000 0.0029(9) C6 0.0976(8) 0.0586(6) 0.0512(7) 0.0010(6) 0.0046(7) 0.0029(6) C7 0.0897(8) 0.0525(6) 0.0485(6) 0.0004(5) -0.0029(6) -0.0104(6) C8 0.0873(11) 0.0469(8) 0.0656(10) 0.000 0.000 -0.0072(8) C9 0.0874(8) 0.0654(7) 0.0666(8) 0.0037(6) -0.0066(7) -0.0072(7) C10 0.0679(12) 0.0911(14) 0.253(2) 0.000 0.000 0.0140(12) C11 0.0729(12) 0.0851(13) 0.213(2) 0.0135(18) -0.0089(18) 0.0290(11) C12 0.0600(10) 0.0591(9) 0.1376(15) 0.000 0.000 0.0119(8) C13 0.0745(11) 0.0593(10) 0.2801(17) 0.000 0.000 0.0187(9) C14 0.0791(13) 0.0633(11) 0.429(2) 0.000 0.000 0.0140(11) C15 0.0947(15) 0.0638(13) 0.339(2) 0.0093(19) -0.020(2) 0.0178(13) C16 0.0816(13) 0.0630(12) 0.380(2) 0.000 0.000 0.0135(11) C17 0.0792(14) 0.0646(12) 0.440(2) 0.000 0.000 0.0078(12) C18 0.0815(13) 0.0647(12) 0.254(2) 0.0070(16) -0.0169(16) 0.0131(11) O5 2.00(5) 0.285(8) 0.499(15) 0.000 0.000 0.031(16) C2 0.0997(18) 0.0700(15) 0.0628(15) -0.0106(14) -0.0037(16) 0.0165(15) C19 0.0979(18) 0.112(2) 0.0903(19) 0.0120(18) -0.0158(17) -0.0244(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.0130(11) . ? Co1 O2 2.0130(11) 6 ? Co1 N2 2.0336(16) . ? Co1 N1 2.052(2) . ? N1 C1 1.318(4) 6 ? N1 C1 1.318(4) . ? N1 C19 1.382(4) 6 ? N1 C19 1.382(4) . ? N2 C12 1.295(3) . ? N2 C10 1.358(3) . ? N3 C12 1.334(3) . ? N3 C11 1.386(3) . ? N3 C11 1.386(3) 6 ? N3 C13 1.417(3) . ? O1 C9 1.2167(19) . ? O2 C9 1.2581(18) . ? C1 C19 1.199(5) . ? C1 C3 1.381(5) 8_546 ? C1 C2 1.870(5) 8_546 ? C1 C1 1.930(7) 6 ? C3 C2 1.223(5) . ? C3 C1 1.381(5) 7_656 ? C3 C4 1.378(4) . ? C3 C19 1.800(5) 7_656 ? C4 C3 1.378(4) 6_556 ? C4 C2 1.410(4) . ? C4 C2 1.410(4) 6_556 ? C4 C5 1.464(3) . ? C5 C6 1.3899(18) . ? C5 C6 1.3899(18) 6_556 ? C6 C7 1.375(2) . ? C7 C8 1.3931(17) . ? C7 C9 1.511(2) . ? C8 C7 1.3931(17) 6_556 ? C10 C11 1.358(4) . ? C10 C11 1.358(4) 6 ? C11 C11 0.663(11) 6 ? C13 C14 1.343(4) . ? C13 C18 1.402(4) . ? C13 C18 1.402(4) 6 ? C14 C15 1.489(4) 6 ? C14 C15 1.489(4) . ? C15 C15 1.043(13) 6 ? C15 C16 1.406(5) . ? C16 C17 1.354(4) . ? C16 C15 1.406(5) 6 ? C16 C16 1.489(5) 5_665 ? C17 C18 1.446(4) 6 ? C17 C18 1.446(4) . ? C18 C18 0.938(11) 6 ? C2 C19 1.377(5) 7_656 ? C2 C1 1.870(5) 7_656 ? C2 C2 2.002(7) 6_556 ? C19 C2 1.377(5) 8_546 ? C19 C3 1.800(5) 8_546 ? C19 C19 1.944(8) 6 ? 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 O2 Co1 O2 93.41(6) . 6 ? O2 Co1 N2 107.34(4) . . ? O2 Co1 N2 107.34(4) 6 . ? O2 Co1 N1 100.41(5) . . ? O2 Co1 N1 100.41(5) 6 . ? N2 Co1 N1 138.97(7) . . ? C1 N1 C1 94.2(3) 6 . ? C1 N1 C19 52.6(2) 6 6 ? C1 N1 C19 115.0(3) . 6 ? C1 N1 C19 115.0(3) 6 . ? C1 N1 C19 52.6(2) . . ? C19 N1 C19 89.4(3) 6 . ? C1 N1 Co1 126.38(17) 6 . ? C1 N1 Co1 126.38(17) . . ? C19 N1 Co1 117.39(18) 6 . ? C19 N1 Co1 117.39(18) . . ? C12 N2 C10 104.61(18) . . ? C12 N2 Co1 126.92(14) . . ? C10 N2 Co1 128.47(15) . . ? C12 N3 C11 104.50(18) . . ? C12 N3 C11 104.50(18) . 6 ? C11 N3 C11 27.7(5) . 6 ? C12 N3 C13 127.78(18) . . ? C11 N3 C13 126.02(19) . . ? C11 N3 C13 126.02(19) 6 . ? C9 O2 Co1 103.64(10) . . ? C19 C1 N1 66.4(3) . . ? C19 C1 C3 88.2(3) . 8_546 ? N1 C1 C3 124.6(3) . 8_546 ? C19 C1 C2 47.4(2) . 8_546 ? N1 C1 C2 98.3(2) . 8_546 ? C3 C1 C2 40.8(2) 8_546 8_546 ? C19 C1 C1 90.3(2) . 6 ? N1 C1 C1 42.92(16) . 6 ? C3 C1 C1 92.57(19) 8_546 6 ? C2 C1 C1 91.10(15) 8_546 6 ? C2 C3 C1 91.6(3) . 7_656 ? C2 C3 C4 65.4(3) . . ? C1 C3 C4 120.6(3) 7_656 . ? C2 C3 C19 49.9(3) . 7_656 ? C1 C3 C19 41.7(2) 7_656 7_656 ? C4 C3 C19 97.2(2) . 7_656 ? C3 C4 C3 96.4(3) . 6_556 ? C3 C4 C2 52.0(2) . . ? C3 C4 C2 116.3(3) 6_556 . ? C3 C4 C2 116.3(3) . 6_556 ? C3 C4 C2 52.0(2) 6_556 6_556 ? C2 C4 C2 90.4(3) . 6_556 ? C3 C4 C5 123.22(17) . . ? C3 C4 C5 123.22(17) 6_556 . ? C2 C4 C5 120.0(2) . . ? C2 C4 C5 120.0(2) 6_556 . ? C6 C5 C6 118.02(19) . 6_556 ? C6 C5 C4 120.99(10) . . ? C6 C5 C4 120.99(10) 6_556 . ? C7 C6 C5 121.27(14) . . ? C6 C7 C8 120.39(13) . . ? C6 C7 C9 119.25(12) . . ? C8 C7 C9 120.36(14) . . ? C7 C8 C7 118.66(19) 6_556 . ? O1 C9 O2 122.91(14) . . ? O1 C9 C7 119.12(13) . . ? O2 C9 C7 117.94(13) . . ? N2 C10 C11 108.9(2) . . ? N2 C10 C11 108.9(2) . 6 ? C11 C10 C11 28.3(5) . 6 ? C11 C11 C10 75.9(2) 6 . ? C11 C11 N3 76.2(2) 6 . ? C10 C11 N3 103.6(3) . . ? N2 C12 N3 112.78(18) . . ? C14 C13 C18 116.1(2) . . ? C14 C13 C18 116.1(2) . 6 ? C18 C13 C18 39.1(4) . 6 ? C14 C13 N3 119.4(2) . . ? C18 C13 N3 120.6(2) . . ? C18 C13 N3 120.6(2) 6 . ? C13 C14 C15 116.3(3) . 6 ? C13 C14 C15 116.3(3) . . ? C15 C14 C15 41.0(5) 6 . ? C15 C15 C16 68.2(3) 6 . ? C15 C15 C14 69.5(2) 6 . ? C16 C15 C14 111.8(3) . . ? C17 C16 C15 112.9(2) . . ? C17 C16 C15 112.9(2) . 6 ? C15 C16 C15 43.6(5) . 6 ? C17 C16 C16 121.7(3) . 5_665 ? C15 C16 C16 120.9(3) . 5_665 ? C15 C16 C16 120.9(3) 6 5_665 ? C16 C17 C18 119.9(3) . 6 ? C16 C17 C18 119.9(3) . . ? C18 C17 C18 37.9(4) 6 . ? C18 C18 C13 70.5(2) 6 . ? C18 C18 C17 71.1(2) 6 . ? C13 C18 C17 111.5(3) . . ? C3 C2 C19 87.4(3) . 7_656 ? C3 C2 C4 62.6(2) . . ? C19 C2 C4 118.9(3) 7_656 . ? C3 C2 C1 47.6(2) . 7_656 ? C19 C2 C1 39.8(2) 7_656 7_656 ? C4 C2 C1 92.8(2) . 7_656 ? C3 C2 C2 91.2(2) . 6_556 ? C19 C2 C2 88.8(2) 7_656 6_556 ? C4 C2 C2 44.78(16) . 6_556 ? C1 C2 C2 88.90(15) 7_656 6_556 ? C1 C19 C2 92.8(3) . 8_546 ? C1 C19 N1 60.9(2) . . ? C2 C19 N1 124.1(3) 8_546 . ? C1 C19 C3 50.1(2) . 8_546 ? C2 C19 C3 42.7(2) 8_546 8_546 ? N1 C19 C3 96.5(2) . 8_546 ? C1 C19 C19 89.7(2) . 6 ? C2 C19 C19 91.2(2) 8_546 6 ? N1 C19 C19 45.31(17) . 6 ? C3 C19 C19 91.75(15) 8_546 6 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.658 _refine_diff_density_min -0.968 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 937594' ####################################################################### # # 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 ? _chemical_formula_sum 'C13 H13 Co N O7' _chemical_formula_weight 354.17 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 17.465(18) _cell_length_b 9.797(10) _cell_length_c 16.253(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.207(12) _cell_angle_gamma 90.00 _cell_volume 2696(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 1.310 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7796 _exptl_absorpt_correction_T_max 0.7796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7262 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2374 _reflns_number_gt 1915 _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^)+(0.0502P)^2^+0.5983P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2374 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.35340(2) 0.44400(4) 0.23412(2) 0.02593(16) Uani 1 1 d . . . O3 O 0.27805(11) 0.4526(2) 0.31514(13) 0.0366(5) Uani 1 1 d . . . H3B H 0.2320 0.5058 0.3082 0.044 Uiso 1 1 d R . . H3 H 0.3041 0.4554 0.3645 0.055 Uiso 1 1 d R . . C6 C 0.43945(14) 1.0529(3) 0.31676(16) 0.0188(6) Uani 1 1 d . . . O1 O 0.42690(11) 0.4119(2) 0.14456(13) 0.0336(5) Uani 1 1 d . . . H1C H 0.4647 0.4828 0.1396 0.040 Uiso 1 1 d R . . H1B H 0.4598 0.3525 0.1628 0.050 Uiso 1 1 d R . . C7 C 0.41614(14) 0.9214(3) 0.29226(17) 0.0191(6) Uani 1 1 d . . . H7 H 0.3720 0.9065 0.2477 0.023 Uiso 1 1 calc R . . C4 C 0.55258(14) 0.9651(3) 0.42235(16) 0.0187(6) Uani 1 1 d . . . N1 N 0.25947(12) 0.4690(2) 0.12653(14) 0.0253(5) Uani 1 1 d . . . O2 O 0.42074(10) 0.29093(19) 0.29643(13) 0.0324(5) Uani 1 1 d . . . O6 O 0.33002(10) 1.1566(2) 0.21911(13) 0.0377(6) Uani 1 1 d . . . C2 C 0.45837(14) 0.8122(3) 0.33396(17) 0.0196(6) Uani 1 1 d . . . O4 O 0.38614(12) 0.6443(2) 0.24110(14) 0.0412(6) Uani 1 1 d . . . C5 C 0.50744(14) 1.0736(3) 0.38169(16) 0.0201(6) Uani 1 1 d . . . H5 H 0.5229 1.1623 0.3982 0.024 Uiso 1 1 calc R . . C3 C 0.52648(14) 0.8343(3) 0.39817(16) 0.0216(6) Uani 1 1 d . . . H3A H 0.5549 0.7599 0.4253 0.026 Uiso 1 1 calc R . . C1 C 0.43190(15) 0.6687(3) 0.31236(19) 0.0277(7) Uani 1 1 d . . . O5 O 0.45556(12) 0.5776(2) 0.36674(16) 0.0459(6) Uani 1 1 d . . . C8 C 0.39269(15) 1.1728(3) 0.27391(17) 0.0233(6) Uani 1 1 d . . . C11 C 0.16848(16) 0.6185(3) 0.03626(19) 0.0347(8) Uani 1 1 d . . . H11 H 0.1530 0.7080 0.0219 0.042 Uiso 1 1 calc R . . C12 C 0.23320(16) 0.5938(3) 0.1020(2) 0.0350(8) Uani 1 1 d . . . H12 H 0.2602 0.6682 0.1309 0.042 Uiso 1 1 calc R . . C9 C 0.62573(14) 0.9889(3) 0.49099(16) 0.0198(6) Uani 1 1 d . . . C10 C 0.65490(16) 1.1169(3) 0.51526(19) 0.0352(8) Uani 1 1 d . . . H10 H 0.6306 1.1929 0.4857 0.042 Uiso 1 1 calc R . . C13 C 0.21965(16) 0.3656(3) 0.08279(19) 0.0331(8) Uani 1 1 d . . . H13 H 0.2363 0.2771 0.0985 0.040 Uiso 1 1 calc R . . O7 O 0.37272(17) 0.4700(3) 0.47524(16) 0.0748(9) Uani 1 1 d . . . H7D H 0.3639 0.5559 0.4652 0.090 Uiso 1 1 d R . . H7C H 0.3738 0.4996 0.5257 0.090 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0234(2) 0.0212(2) 0.0268(3) 0.00159(17) -0.00600(15) 0.00373(16) O3 0.0277(10) 0.0420(13) 0.0356(13) -0.0011(10) -0.0007(9) 0.0069(9) C6 0.0177(12) 0.0203(14) 0.0173(14) 0.0026(12) 0.0020(10) 0.0005(10) O1 0.0300(10) 0.0291(12) 0.0394(13) 0.0024(10) 0.0040(9) 0.0034(9) C7 0.0162(12) 0.0190(15) 0.0194(14) -0.0011(11) -0.0008(10) -0.0018(10) C4 0.0194(12) 0.0185(15) 0.0164(13) -0.0007(12) 0.0008(10) -0.0011(10) N1 0.0225(11) 0.0241(13) 0.0246(13) -0.0009(11) -0.0036(9) 0.0019(10) O2 0.0292(10) 0.0160(11) 0.0467(13) 0.0040(9) -0.0008(9) 0.0022(8) O6 0.0242(10) 0.0349(13) 0.0434(13) 0.0141(10) -0.0121(9) 0.0004(9) C2 0.0189(12) 0.0194(15) 0.0198(14) -0.0029(12) 0.0034(10) -0.0016(11) O4 0.0403(11) 0.0295(13) 0.0464(14) -0.0163(11) -0.0034(10) -0.0091(10) C5 0.0209(13) 0.0152(14) 0.0217(15) -0.0014(11) 0.0005(11) -0.0037(10) C3 0.0212(13) 0.0181(15) 0.0218(15) 0.0030(12) -0.0020(11) 0.0023(11) C1 0.0200(13) 0.0204(16) 0.0418(19) -0.0071(14) 0.0059(13) -0.0005(11) O5 0.0409(12) 0.0184(12) 0.0741(18) 0.0070(11) 0.0057(12) 0.0017(10) C8 0.0223(13) 0.0206(16) 0.0261(16) 0.0068(13) 0.0041(11) 0.0026(11) C11 0.0320(15) 0.0200(16) 0.0414(19) 0.0014(14) -0.0118(13) -0.0028(12) C12 0.0301(15) 0.0227(16) 0.041(2) -0.0020(14) -0.0116(13) -0.0040(13) C9 0.0212(12) 0.0208(14) 0.0160(14) 0.0000(12) 0.0018(10) -0.0013(11) C10 0.0355(16) 0.0224(16) 0.0353(18) 0.0062(14) -0.0150(14) -0.0019(13) C13 0.0346(15) 0.0200(16) 0.0345(18) 0.0002(14) -0.0114(13) 0.0044(13) O7 0.095(2) 0.086(2) 0.0353(16) -0.0043(15) 0.0018(14) -0.0102(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.018(2) . ? Co1 O4 2.039(3) . ? Co1 O3 2.079(3) . ? Co1 N1 2.098(3) . ? Co1 O1 2.187(3) . ? O3 H3B 0.9412 . ? O3 H3 0.8200 . ? C6 C7 1.380(4) . ? C6 C5 1.396(3) . ? C6 C8 1.501(4) . ? O1 H1C 0.9758 . ? O1 H1B 0.8200 . ? C7 C2 1.379(4) . ? C7 H7 0.9300 . ? C4 C3 1.385(4) . ? C4 C5 1.390(4) . ? C4 C9 1.494(3) . ? N1 C13 1.332(4) . ? N1 C12 1.332(4) . ? O2 C8 1.275(3) 1_545 ? O6 C8 1.240(3) . ? C2 C3 1.393(3) . ? C2 C1 1.495(4) . ? O4 C1 1.258(3) . ? C5 H5 0.9300 . ? C3 H3A 0.9300 . ? C1 O5 1.252(4) . ? C8 O2 1.275(3) 1_565 ? C11 C12 1.373(4) . ? C11 C9 1.391(4) 8_465 ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C9 C10 1.375(4) . ? C9 C11 1.391(4) 8_566 ? C10 C13 1.380(4) 8_566 ? C10 H10 0.9300 . ? C13 C10 1.380(4) 8_465 ? C13 H13 0.9300 . ? O7 H7D 0.8644 . ? O7 H7C 0.8656 . ? 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 O2 Co1 O4 124.48(10) . . ? O2 Co1 O3 95.39(10) . . ? O4 Co1 O3 97.94(9) . . ? O2 Co1 N1 138.18(9) . . ? O4 Co1 N1 94.88(9) . . ? O3 Co1 N1 92.07(12) . . ? O2 Co1 O1 82.07(10) . . ? O4 Co1 O1 88.47(9) . . ? O3 Co1 O1 173.44(8) . . ? N1 Co1 O1 85.91(12) . . ? Co1 O3 H3B 127.0 . . ? Co1 O3 H3 109.6 . . ? H3B O3 H3 110.6 . . ? C7 C6 C5 119.3(2) . . ? C7 C6 C8 120.6(2) . . ? C5 C6 C8 120.2(2) . . ? Co1 O1 H1C 118.2 . . ? Co1 O1 H1B 109.5 . . ? H1C O1 H1B 96.1 . . ? C2 C7 C6 119.9(2) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C3 C4 C5 117.6(2) . . ? C3 C4 C9 121.2(2) . . ? C5 C4 C9 121.2(2) . . ? C13 N1 C12 116.2(2) . . ? C13 N1 Co1 123.73(19) . . ? C12 N1 Co1 119.89(18) . . ? C8 O2 Co1 113.26(17) 1_545 . ? C7 C2 C3 120.2(2) . . ? C7 C2 C1 121.1(2) . . ? C3 C2 C1 118.7(2) . . ? C1 O4 Co1 109.9(2) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? O5 C1 O4 122.7(3) . . ? O5 C1 C2 118.3(3) . . ? O4 C1 C2 119.0(3) . . ? O6 C8 O2 122.1(2) . 1_565 ? O6 C8 C6 121.1(2) . . ? O2 C8 C6 116.8(2) 1_565 . ? C12 C11 C9 120.7(3) . 8_465 ? C12 C11 H11 119.7 . . ? C9 C11 H11 119.7 8_465 . ? N1 C12 C11 123.5(3) . . ? N1 C12 H12 118.2 . . ? C11 C12 H12 118.2 . . ? C10 C9 C11 115.2(2) . 8_566 ? C10 C9 C4 123.0(2) . . ? C11 C9 C4 121.8(2) 8_566 . ? C9 C10 C13 121.0(3) . 8_566 ? C9 C10 H10 119.5 . . ? C13 C10 H10 119.5 8_566 . ? N1 C13 C10 123.3(3) . 8_465 ? N1 C13 H13 118.4 . . ? C10 C13 H13 118.4 8_465 . ? H7D O7 H7C 79.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C6 C7 C2 2.3(4) . . . . ? C8 C6 C7 C2 -178.0(2) . . . . ? O2 Co1 N1 C13 9.1(3) . . . . ? O4 Co1 N1 C13 170.5(2) . . . . ? O3 Co1 N1 C13 -91.4(2) . . . . ? O1 Co1 N1 C13 82.4(2) . . . . ? O2 Co1 N1 C12 -175.5(2) . . . . ? O4 Co1 N1 C12 -14.1(2) . . . . ? O3 Co1 N1 C12 84.0(2) . . . . ? O1 Co1 N1 C12 -102.3(2) . . . . ? O4 Co1 O2 C8 -171.34(18) . . . 1_545 ? O3 Co1 O2 C8 85.2(2) . . . 1_545 ? N1 Co1 O2 C8 -14.0(3) . . . 1_545 ? O1 Co1 O2 C8 -88.7(2) . . . 1_545 ? C6 C7 C2 C3 -2.9(4) . . . . ? C6 C7 C2 C1 176.3(2) . . . . ? O2 Co1 O4 C1 -29.7(2) . . . . ? O3 Co1 O4 C1 72.5(2) . . . . ? N1 Co1 O4 C1 165.30(19) . . . . ? O1 Co1 O4 C1 -108.9(2) . . . . ? C3 C4 C5 C6 -2.0(4) . . . . ? C9 C4 C5 C6 179.2(2) . . . . ? C7 C6 C5 C4 0.2(4) . . . . ? C8 C6 C5 C4 -179.5(2) . . . . ? C5 C4 C3 C2 1.5(4) . . . . ? C9 C4 C3 C2 -179.8(2) . . . . ? C7 C2 C3 C4 1.0(4) . . . . ? C1 C2 C3 C4 -178.3(2) . . . . ? Co1 O4 C1 O5 3.8(3) . . . . ? Co1 O4 C1 C2 -175.28(19) . . . . ? C7 C2 C1 O5 -157.9(3) . . . . ? C3 C2 C1 O5 21.4(4) . . . . ? C7 C2 C1 O4 21.2(4) . . . . ? C3 C2 C1 O4 -159.5(3) . . . . ? C7 C6 C8 O6 4.0(4) . . . . ? C5 C6 C8 O6 -176.3(3) . . . . ? C7 C6 C8 O2 -175.7(2) . . . 1_565 ? C5 C6 C8 O2 3.9(4) . . . 1_565 ? C13 N1 C12 C11 0.7(5) . . . . ? Co1 N1 C12 C11 -175.0(3) . . . . ? C9 C11 C12 N1 0.3(5) 8_465 . . . ? C3 C4 C9 C10 178.1(3) . . . . ? C5 C4 C9 C10 -3.2(4) . . . . ? C3 C4 C9 C11 -3.2(4) . . . 8_566 ? C5 C4 C9 C11 175.5(3) . . . 8_566 ? C11 C9 C10 C13 -3.2(5) 8_566 . . 8_566 ? C4 C9 C10 C13 175.6(3) . . . 8_566 ? C12 N1 C13 C10 0.3(5) . . . 8_465 ? Co1 N1 C13 C10 175.9(2) . . . 8_465 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.359 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 937595' ####################################################################### # # 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 ? _chemical_formula_sum 'C14 H0 N Ni O5' _chemical_formula_weight 320.86 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' Ni Ni 0.3393 1.1124 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.233(3) _cell_length_b 10.039(5) _cell_length_c 10.219(5) _cell_angle_alpha 114.141(5) _cell_angle_beta 99.715(5) _cell_angle_gamma 103.757(6) _cell_volume 627.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 1.566 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3507 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2166 _reflns_number_gt 1832 _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^)+(0.0454P)^2^+1.1702P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2166 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Ni1 Ni 0.08554(7) 0.87656(6) -0.11572(5) 0.02355(18) Uani 1 1 d . . . O1 O 0.1064(4) 0.6689(3) -0.1390(3) 0.0258(6) Uani 1 1 d . . . O2 O 0.3122(4) 0.8747(3) 0.0640(3) 0.0278(6) Uani 1 1 d . . . O3 O 0.3071(4) 0.8952(4) -0.2201(3) 0.0383(7) Uani 1 1 d . . . H3B H 0.4432 0.9431 -0.1781 0.046 Uiso 1 1 d R . . H3 H 0.2589 0.8854 -0.3035 0.046 Uiso 1 1 d R . . O4 O 0.1078(5) 0.1388(3) -0.2306(3) 0.0379(8) Uani 1 1 d . . . O5 O 0.1116(4) 0.1049(3) -0.0263(3) 0.0253(6) Uani 1 1 d . . . O6 O 0.8231(7) 0.0872(5) 0.4832(5) 0.0773(13) Uani 1 1 d . . . H6A H 0.8510 0.2008 0.5627 0.093 Uiso 1 1 d R . . H6B H 0.8994 0.1010 0.5890 0.093 Uiso 1 1 d R . . C1 C 0.1464(6) 0.1905(4) -0.0936(4) 0.0233(8) Uani 1 1 d . . . C2 C 0.2416(5) 0.3625(4) 0.0074(4) 0.0200(8) Uani 1 1 d . . . C3 C 0.2049(5) 0.4631(4) -0.0470(4) 0.0192(8) Uani 1 1 d . . . H3A H 0.1260 0.4237 -0.1453 0.023 Uiso 1 1 calc R . . C4 C 0.2867(5) 0.6231(4) 0.0462(4) 0.0186(8) Uani 1 1 d . . . C5 C 0.4059(5) 0.6818(4) 0.1921(4) 0.0222(8) Uani 1 1 d . . . H5 H 0.4575 0.7886 0.2544 0.027 Uiso 1 1 calc R . . C6 C 0.4495(5) 0.5826(4) 0.2468(4) 0.0206(8) Uani 1 1 d . . . C7 C 0.3646(5) 0.4224(4) 0.1530(4) 0.0219(8) Uani 1 1 d . . . H7 H 0.3907 0.3549 0.1885 0.026 Uiso 1 1 calc R . . C8 C 0.5880(5) 0.6461(4) 0.3997(4) 0.0221(8) Uani 1 1 d . . . C9 C 0.5961(6) 0.7828(5) 0.5182(4) 0.0291(9) Uani 1 1 d . . . H9 H 0.5079 0.8331 0.5041 0.035 Uiso 1 1 calc R . . C10 C 0.7352(6) 0.8444(5) 0.6574(4) 0.0287(9) Uani 1 1 d . . . H10 H 0.7385 0.9365 0.7346 0.034 Uiso 1 1 calc R . . C11 C 0.8523(7) 0.6413(5) 0.5724(4) 0.0346(10) Uani 1 1 d . . . H11 H 0.9380 0.5910 0.5912 0.041 Uiso 1 1 calc R . . C12 C 0.7192(6) 0.5736(5) 0.4311(4) 0.0307(10) Uani 1 1 d . . . H12 H 0.7166 0.4798 0.3567 0.037 Uiso 1 1 calc R . . C13 C 0.2363(5) 0.7289(4) -0.0128(4) 0.0214(8) Uani 1 1 d . . . N1 N 0.8647(5) 0.7775(4) 0.6855(3) 0.0245(7) 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 Ni1 0.0289(3) 0.0182(3) 0.0195(3) 0.0087(2) -0.0014(2) 0.0076(2) O1 0.0307(15) 0.0242(15) 0.0205(14) 0.0126(12) -0.0020(11) 0.0092(12) O2 0.0344(16) 0.0192(15) 0.0273(14) 0.0117(12) 0.0025(12) 0.0080(12) O3 0.0308(16) 0.0454(19) 0.0334(16) 0.0187(15) 0.0043(13) 0.0077(14) O4 0.059(2) 0.0245(16) 0.0183(15) 0.0072(12) 0.0017(13) 0.0066(14) O5 0.0346(15) 0.0155(14) 0.0239(14) 0.0102(11) 0.0038(12) 0.0072(12) O6 0.089(3) 0.088(3) 0.067(3) 0.046(3) 0.018(2) 0.036(3) C1 0.027(2) 0.017(2) 0.025(2) 0.0104(17) 0.0035(16) 0.0077(16) C2 0.0205(19) 0.0186(19) 0.0189(18) 0.0088(16) 0.0028(15) 0.0051(15) C3 0.0202(18) 0.0175(19) 0.0176(18) 0.0081(15) 0.0019(14) 0.0052(15) C4 0.0179(18) 0.022(2) 0.0230(19) 0.0150(16) 0.0074(15) 0.0088(15) C5 0.025(2) 0.0181(19) 0.0211(19) 0.0095(16) 0.0033(16) 0.0055(16) C6 0.0194(18) 0.024(2) 0.0174(18) 0.0102(16) 0.0024(15) 0.0062(15) C7 0.025(2) 0.022(2) 0.0242(19) 0.0150(17) 0.0056(16) 0.0096(16) C8 0.0233(19) 0.023(2) 0.0180(18) 0.0106(16) 0.0019(15) 0.0049(16) C9 0.031(2) 0.028(2) 0.024(2) 0.0083(18) 0.0002(17) 0.0155(18) C10 0.031(2) 0.028(2) 0.0181(19) 0.0047(17) 0.0008(16) 0.0111(18) C11 0.037(2) 0.038(3) 0.026(2) 0.013(2) -0.0006(19) 0.021(2) C12 0.040(2) 0.027(2) 0.0182(19) 0.0054(17) -0.0012(17) 0.0164(19) C13 0.026(2) 0.020(2) 0.0230(19) 0.0135(17) 0.0075(16) 0.0096(16) N1 0.0267(17) 0.0248(18) 0.0193(16) 0.0107(14) 0.0002(13) 0.0082(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 Ni1 O5 2.037(3) 1_565 ? Ni1 N1 2.041(3) 1_454 ? Ni1 O1 2.045(3) . ? Ni1 O3 2.083(3) . ? Ni1 O5 2.186(3) 2_565 ? Ni1 O2 2.256(3) . ? Ni1 C13 2.479(4) . ? O1 C13 1.263(4) . ? O2 C13 1.262(4) . ? O3 H3B 0.9207 . ? O3 H3 0.8200 . ? O4 C1 1.230(5) . ? O5 C1 1.309(4) . ? O5 Ni1 2.037(3) 1_545 ? O5 Ni1 2.186(3) 2_565 ? O6 H6A 1.0389 . ? O6 H6B 1.0645 . ? C1 C2 1.502(5) . ? C2 C7 1.391(5) . ? C2 C3 1.392(5) . ? C3 C4 1.394(5) . ? C3 H3A 0.9300 . ? C4 C5 1.386(5) . ? C4 C13 1.503(5) . ? C5 C6 1.396(5) . ? C5 H5 0.9300 . ? C6 C7 1.398(5) . ? C6 C8 1.485(5) . ? C7 H7 0.9300 . ? C8 C9 1.390(5) . ? C8 C12 1.397(5) . ? C9 C10 1.385(5) . ? C9 H9 0.9300 . ? C10 N1 1.333(5) . ? C10 H10 0.9300 . ? C11 N1 1.351(5) . ? C11 C12 1.375(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? N1 Ni1 2.041(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 O5 Ni1 N1 103.01(11) 1_565 1_454 ? O5 Ni1 O1 162.41(10) 1_565 . ? N1 Ni1 O1 93.87(11) 1_454 . ? O5 Ni1 O3 95.52(11) 1_565 . ? N1 Ni1 O3 91.96(13) 1_454 . ? O1 Ni1 O3 88.75(12) . . ? O5 Ni1 O5 77.07(11) 1_565 2_565 ? N1 Ni1 O5 96.10(12) 1_454 2_565 ? O1 Ni1 O5 96.43(10) . 2_565 ? O3 Ni1 O5 170.09(11) . 2_565 ? O5 Ni1 O2 102.23(10) 1_565 . ? N1 Ni1 O2 154.73(12) 1_454 . ? O1 Ni1 O2 60.87(10) . . ? O3 Ni1 O2 86.97(11) . . ? O5 Ni1 O2 88.19(10) 2_565 . ? O5 Ni1 C13 132.19(11) 1_565 . ? N1 Ni1 C13 124.36(13) 1_454 . ? O1 Ni1 C13 30.53(11) . . ? O3 Ni1 C13 89.46(12) . . ? O5 Ni1 C13 90.74(11) 2_565 . ? O2 Ni1 C13 30.45(11) . . ? C13 O1 Ni1 94.1(2) . . ? C13 O2 Ni1 84.6(2) . . ? Ni1 O3 H3B 129.5 . . ? Ni1 O3 H3 109.7 . . ? H3B O3 H3 116.9 . . ? C1 O5 Ni1 124.8(2) . 1_545 ? C1 O5 Ni1 124.0(2) . 2_565 ? Ni1 O5 Ni1 102.93(11) 1_545 2_565 ? H6A O6 H6B 72.7 . . ? O4 C1 O5 124.3(4) . . ? O4 C1 C2 119.6(3) . . ? O5 C1 C2 116.0(3) . . ? C7 C2 C3 119.7(3) . . ? C7 C2 C1 121.4(3) . . ? C3 C2 C1 118.8(3) . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 120.1 . . ? C5 C4 C3 120.1(3) . . ? C5 C4 C13 121.1(3) . . ? C3 C4 C13 118.7(3) . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C7 118.6(3) . . ? C5 C6 C8 120.6(3) . . ? C7 C6 C8 120.7(3) . . ? C2 C7 C6 120.9(3) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 C8 C12 116.7(3) . . ? C9 C8 C6 121.5(3) . . ? C12 C8 C6 121.9(3) . . ? C10 C9 C8 120.2(4) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? N1 C10 C9 122.9(4) . . ? N1 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N1 C11 C12 123.3(4) . . ? N1 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C11 C12 C8 119.7(4) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? O2 C13 O1 120.0(3) . . ? O2 C13 C4 121.6(3) . . ? O1 C13 C4 118.3(3) . . ? O2 C13 Ni1 64.92(19) . . ? O1 C13 Ni1 55.36(18) . . ? C4 C13 Ni1 168.9(3) . . ? C10 N1 C11 117.2(3) . . ? C10 N1 Ni1 123.2(3) . 1_656 ? C11 N1 Ni1 119.6(3) . 1_656 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Ni1 O1 C13 -13.4(5) 1_565 . . . ? N1 Ni1 O1 C13 -177.1(2) 1_454 . . . ? O3 Ni1 O1 C13 91.1(2) . . . . ? O5 Ni1 O1 C13 -80.5(2) 2_565 . . . ? O2 Ni1 O1 C13 3.8(2) . . . . ? O5 Ni1 O2 C13 170.9(2) 1_565 . . . ? N1 Ni1 O2 C13 -5.9(4) 1_454 . . . ? O1 Ni1 O2 C13 -3.8(2) . . . . ? O3 Ni1 O2 C13 -94.1(2) . . . . ? O5 Ni1 O2 C13 94.5(2) 2_565 . . . ? Ni1 O5 C1 O4 23.6(5) 1_545 . . . ? Ni1 O5 C1 O4 -119.3(4) 2_565 . . . ? Ni1 O5 C1 C2 -155.8(2) 1_545 . . . ? Ni1 O5 C1 C2 61.4(4) 2_565 . . . ? O4 C1 C2 C7 -151.3(4) . . . . ? O5 C1 C2 C7 28.1(5) . . . . ? O4 C1 C2 C3 28.8(6) . . . . ? O5 C1 C2 C3 -151.8(3) . . . . ? C7 C2 C3 C4 -1.9(5) . . . . ? C1 C2 C3 C4 178.0(3) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C2 C3 C4 C13 -177.0(3) . . . . ? C3 C4 C5 C6 1.5(5) . . . . ? C13 C4 C5 C6 179.0(3) . . . . ? C4 C5 C6 C7 -2.2(6) . . . . ? C4 C5 C6 C8 175.9(3) . . . . ? C3 C2 C7 C6 1.1(6) . . . . ? C1 C2 C7 C6 -178.8(4) . . . . ? C5 C6 C7 C2 1.0(6) . . . . ? C8 C6 C7 C2 -177.2(3) . . . . ? C5 C6 C8 C9 34.9(5) . . . . ? C7 C6 C8 C9 -146.9(4) . . . . ? C5 C6 C8 C12 -143.7(4) . . . . ? C7 C6 C8 C12 34.4(6) . . . . ? C12 C8 C9 C10 2.7(6) . . . . ? C6 C8 C9 C10 -176.0(4) . . . . ? C8 C9 C10 N1 -0.6(7) . . . . ? N1 C11 C12 C8 -0.3(7) . . . . ? C9 C8 C12 C11 -2.3(6) . . . . ? C6 C8 C12 C11 176.4(4) . . . . ? Ni1 O2 C13 O1 6.3(3) . . . . ? Ni1 O2 C13 C4 -169.8(3) . . . . ? Ni1 O1 C13 O2 -6.9(4) . . . . ? Ni1 O1 C13 C4 169.3(3) . . . . ? C5 C4 C13 O2 5.4(5) . . . . ? C3 C4 C13 O2 -177.0(3) . . . . ? C5 C4 C13 O1 -170.7(3) . . . . ? C3 C4 C13 O1 6.8(5) . . . . ? C5 C4 C13 Ni1 -117.9(13) . . . . ? C3 C4 C13 Ni1 59.6(15) . . . . ? O5 Ni1 C13 O2 -12.0(3) 1_565 . . . ? N1 Ni1 C13 O2 176.9(2) 1_454 . . . ? O1 Ni1 C13 O2 173.4(4) . . . . ? O3 Ni1 C13 O2 84.9(2) . . . . ? O5 Ni1 C13 O2 -85.2(2) 2_565 . . . ? O5 Ni1 C13 O1 174.6(2) 1_565 . . . ? N1 Ni1 C13 O1 3.6(3) 1_454 . . . ? O3 Ni1 C13 O1 -88.4(2) . . . . ? O5 Ni1 C13 O1 101.5(2) 2_565 . . . ? O2 Ni1 C13 O1 -173.4(4) . . . . ? O5 Ni1 C13 C4 116.2(14) 1_565 . . . ? N1 Ni1 C13 C4 -54.9(14) 1_454 . . . ? O1 Ni1 C13 C4 -58.4(13) . . . . ? O3 Ni1 C13 C4 -146.9(14) . . . . ? O5 Ni1 C13 C4 43.0(14) 2_565 . . . ? O2 Ni1 C13 C4 128.2(15) . . . . ? C9 C10 N1 C11 -2.0(6) . . . . ? C9 C10 N1 Ni1 174.6(3) . . . 1_656 ? C12 C11 N1 C10 2.4(6) . . . . ? C12 C11 N1 Ni1 -174.3(3) . . . 1_656 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.670 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 937597' ####################################################################### # # 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 ? _chemical_formula_sum 'C92 H60 N12 O17 Zn4' _chemical_formula_weight 1867.00 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.344(7) _cell_length_b 13.377(9) _cell_length_c 15.091(10) _cell_angle_alpha 76.574(9) _cell_angle_beta 78.994(8) _cell_angle_gamma 85.999(8) _cell_volume 1993(2) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 1.271 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7852 _exptl_absorpt_correction_T_max 0.7852 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11167 _diffrn_reflns_av_R_equivalents 0.0904 _diffrn_reflns_av_sigmaI/netI 0.1868 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6900 _reflns_number_gt 3155 _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^)+(0.1461P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6900 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1921 _refine_ls_R_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.2814 _refine_ls_wR_factor_gt 0.2324 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _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 0.93815(12) -0.07625(9) 0.24625(8) 0.0363(4) Uani 1 1 d . . . Zn2 Zn 0.56334(12) 0.54371(10) -0.24335(8) 0.0397(4) Uani 1 1 d . . . N1 N 0.5597(10) 0.6754(7) -0.3577(6) 0.051(3) Uani 1 1 d . . . N2 N 0.6265(9) 0.4852(7) -0.3617(6) 0.046(2) Uani 1 1 d . . . N3 N 0.5346(9) 0.3984(7) -0.1435(6) 0.050(3) Uani 1 1 d . . . N4 N 0.9551(9) -0.1695(7) 0.1453(6) 0.044(2) Uani 1 1 d . . . N5 N 0.9346(9) -0.1952(7) 0.3632(6) 0.041(2) Uani 1 1 d . . . N6 N 0.8861(10) -0.0006(7) 0.3608(6) 0.049(2) Uani 1 1 d . . . O1 O 0.7925(7) 0.0087(6) 0.1876(5) 0.054(2) Uani 1 1 d . . . O2 O 0.6790(8) -0.1232(6) 0.2775(6) 0.064(2) Uani 1 1 d . . . O3 O 1.1051(7) -0.0067(6) 0.1936(5) 0.053(2) Uani 1 1 d . . . O4 O 1.2052(9) -0.1384(7) 0.2718(7) 0.088(3) Uani 1 1 d . . . O5 O 0.7059(7) 0.5894(6) -0.1927(5) 0.052(2) Uani 1 1 d . . . O6 O 0.8460(9) 0.4893(8) -0.2646(7) 0.083(3) Uani 1 1 d . . . O7 O 0.3883(8) 0.5954(6) -0.1825(5) 0.055(2) Uani 1 1 d . . . O8 O 0.3215(8) 0.5057(6) -0.2677(5) 0.061(2) Uani 1 1 d . . . O9 O 0.813(3) 0.8136(17) 0.7313(14) 0.160(13) Uani 0.50 1 d P . . C1 C 0.6685(12) 0.3868(9) -0.3591(8) 0.057(3) Uani 1 1 d . . . H1 H 0.6704 0.3427 -0.3017 0.068 Uiso 1 1 calc R . . C2 C 0.7085(14) 0.3490(10) -0.4375(10) 0.072(4) Uani 1 1 d . . . H2 H 0.7350 0.2805 -0.4340 0.086 Uiso 1 1 calc R . . C3 C 0.7077(14) 0.4161(11) -0.5212(9) 0.066(4) Uani 1 1 d . . . H3 H 0.7348 0.3936 -0.5758 0.079 Uiso 1 1 calc R . . C4 C 0.6671(12) 0.5169(11) -0.5244(8) 0.063(4) Uani 1 1 d . . . H4 H 0.6658 0.5621 -0.5813 0.076 Uiso 1 1 calc R . . C5 C 0.6283(11) 0.5510(9) -0.4436(7) 0.049(3) Uani 1 1 d . . . C6 C 0.5893(11) 0.6577(8) -0.4405(7) 0.046(3) Uani 1 1 d . . . C7 C 0.5841(12) 0.7344(10) -0.5196(8) 0.059(3) Uani 1 1 d . . . H7 H 0.6053 0.7193 -0.5778 0.071 Uiso 1 1 calc R . . C8 C 0.5472(15) 0.8330(12) -0.5108(11) 0.081(5) Uani 1 1 d . . . H8 H 0.5434 0.8860 -0.5626 0.098 Uiso 1 1 calc R . . C9 C 0.5158(16) 0.8507(10) -0.4225(12) 0.091(5) Uani 1 1 d . . . H9 H 0.4886 0.9160 -0.4135 0.109 Uiso 1 1 calc R . . C10 C 0.5255(15) 0.7705(11) -0.3479(10) 0.080(5) Uani 1 1 d . . . H10 H 0.5076 0.7832 -0.2886 0.096 Uiso 1 1 calc R . . C11 C 0.2995(11) 0.5625(9) -0.2140(7) 0.043(3) Uani 1 1 d . . . C12 C 0.8182(11) 0.5501(8) -0.2130(7) 0.037(3) Uani 1 1 d . . . C13 C 0.9288(10) 0.5825(8) -0.1741(7) 0.042(3) Uani 1 1 d . . . C14 C 1.0559(10) 0.5586(7) -0.2087(7) 0.038(3) Uani 1 1 d . . . H14 H 1.0730 0.5198 -0.2536 0.046 Uiso 1 1 calc R . . C15 C 1.1598(11) 0.5915(8) -0.1778(8) 0.046(3) Uani 1 1 d . . . C16 C 1.1325(11) 0.6484(8) -0.1104(8) 0.047(3) Uani 1 1 d . . . H16 H 1.2012 0.6709 -0.0890 0.056 Uiso 1 1 calc R . . C17 C 0.8999(11) 0.6373(9) -0.1066(7) 0.049(3) Uani 1 1 d . . . H17 H 0.8126 0.6511 -0.0825 0.059 Uiso 1 1 calc R . . C18 C 0.5716(12) 0.3915(9) -0.0615(8) 0.057(3) Uani 1 1 d . . . H18 H 0.6149 0.4466 -0.0537 0.068 Uiso 1 1 calc R . . C19 C 0.5497(12) 0.3106(8) 0.0089(7) 0.050(3) Uani 1 1 d . . . H19 H 0.5774 0.3098 0.0641 0.060 Uiso 1 1 calc R . . C20 C 0.4844(10) 0.2259(7) -0.0005(7) 0.033(2) Uani 1 1 d . . . C21 C 0.4413(12) 0.2311(9) -0.0814(8) 0.057(3) Uani 1 1 d . . . H21 H 0.3960 0.1771 -0.0895 0.068 Uiso 1 1 calc R . . C22 C 0.4670(11) 0.3201(8) -0.1523(8) 0.048(3) Uani 1 1 d . . . H22 H 0.4361 0.3250 -0.2072 0.058 Uiso 1 1 calc R . . C23 C 0.4641(11) 0.1345(8) 0.0765(7) 0.046(3) Uani 1 1 d . . . C24 C 0.3495(11) 0.0827(8) 0.1085(7) 0.046(3) Uani 1 1 d . . . H24 H 0.2765 0.1074 0.0816 0.055 Uiso 1 1 calc R . . C25 C 0.3371(11) -0.0042(8) 0.1786(8) 0.047(3) Uani 1 1 d . . . C26 C 0.4452(10) -0.0462(8) 0.2175(7) 0.040(3) Uani 1 1 d . . . H26 H 0.4385 -0.1059 0.2640 0.048 Uiso 1 1 calc R . . C27 C 0.5664(10) 0.0049(8) 0.1839(7) 0.041(3) Uani 1 1 d . . . C28 C 0.5748(11) 0.0935(8) 0.1147(8) 0.049(3) Uani 1 1 d . . . H28 H 0.6548 0.1263 0.0933 0.059 Uiso 1 1 calc R . . C29 C 0.6880(11) -0.0430(8) 0.2201(7) 0.044(3) Uani 1 1 d . . . C30 C 0.8636(13) 0.1004(9) 0.3523(9) 0.064(4) Uani 1 1 d . . . H30 H 0.8763 0.1436 0.2936 0.077 Uiso 1 1 calc R . . C31 C 0.8222(15) 0.1418(11) 0.4281(11) 0.080(5) Uani 1 1 d . . . H31 H 0.8057 0.2122 0.4215 0.096 Uiso 1 1 calc R . . C32 C 0.8056(14) 0.0770(12) 0.5143(10) 0.073(4) Uani 1 1 d . . . H32 H 0.7784 0.1035 0.5668 0.088 Uiso 1 1 calc R . . C33 C 0.8289(13) -0.0259(10) 0.5232(9) 0.066(4) Uani 1 1 d . . . H33 H 0.8176 -0.0708 0.5811 0.079 Uiso 1 1 calc R . . C34 C 0.8697(11) -0.0612(9) 0.4433(8) 0.050(3) Uani 1 1 d . . . C35 C 0.8996(10) -0.1721(8) 0.4460(7) 0.041(3) Uani 1 1 d . . . C36 C 0.8959(12) -0.2464(10) 0.5260(8) 0.057(3) Uani 1 1 d . . . H36 H 0.8694 -0.2289 0.5831 0.068 Uiso 1 1 calc R . . C37 C 0.9312(13) -0.3470(9) 0.5224(9) 0.063(4) Uani 1 1 d . . . H37 H 0.9282 -0.3984 0.5762 0.076 Uiso 1 1 calc R . . C38 C 0.9703(13) -0.3680(9) 0.4378(9) 0.064(4) Uani 1 1 d . . . H38 H 0.9967 -0.4346 0.4326 0.077 Uiso 1 1 calc R . . C39 C 0.9710(11) -0.2933(8) 0.3614(8) 0.049(3) Uani 1 1 d . . . H39 H 0.9980 -0.3101 0.3041 0.059 Uiso 1 1 calc R . . C40 C 1.2067(11) -0.0586(9) 0.2190(8) 0.042(3) Uani 1 1 d . . . C41 C 1.0379(13) -0.1379(9) 0.0636(8) 0.060(4) Uani 1 1 d . . . H41 H 1.0887 -0.0810 0.0567 0.072 Uiso 1 1 calc R . . C42 C 1.0508(12) -0.1838(9) -0.0079(7) 0.051(3) Uani 1 1 d . . . H42 H 1.1074 -0.1574 -0.0630 0.061 Uiso 1 1 calc R . . C43 C 0.9793(10) -0.2712(7) 0.0005(7) 0.036(3) Uani 1 1 d . . . C44 C 0.8910(11) -0.3030(8) 0.0814(7) 0.049(3) Uani 1 1 d . . . H44 H 0.8386 -0.3591 0.0887 0.058 Uiso 1 1 calc R . . C45 C 0.8804(11) -0.2508(9) 0.1523(7) 0.049(3) Uani 1 1 d . . . H45 H 0.8198 -0.2726 0.2064 0.059 Uiso 1 1 calc R . . C46 C 1.0009(11) -0.3275(8) -0.0740(8) 0.048(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0356(8) 0.0455(8) 0.0276(7) -0.0045(5) -0.0117(6) 0.0040(6) Zn2 0.0372(8) 0.0576(9) 0.0246(7) -0.0070(6) -0.0075(6) -0.0058(6) N1 0.070(7) 0.056(6) 0.026(5) -0.003(4) -0.003(5) -0.023(5) N2 0.049(6) 0.062(6) 0.027(5) -0.006(4) -0.010(4) -0.011(5) N3 0.050(6) 0.054(6) 0.052(6) -0.021(5) -0.012(5) 0.002(5) N4 0.044(6) 0.046(5) 0.046(6) -0.007(4) -0.022(5) -0.002(4) N5 0.041(6) 0.053(6) 0.033(5) -0.019(4) -0.003(4) -0.008(4) N6 0.066(7) 0.050(6) 0.029(5) -0.007(4) -0.012(5) 0.005(5) O1 0.034(5) 0.067(5) 0.064(6) -0.007(4) -0.030(4) 0.009(4) O2 0.054(6) 0.073(6) 0.061(6) 0.005(5) -0.028(4) 0.008(5) O3 0.034(5) 0.067(5) 0.061(5) -0.013(4) -0.022(4) 0.004(4) O4 0.055(6) 0.077(7) 0.114(8) 0.024(6) -0.021(6) -0.010(5) O5 0.036(5) 0.074(5) 0.055(5) -0.021(4) -0.019(4) -0.008(4) O6 0.060(7) 0.111(8) 0.103(8) -0.055(7) -0.042(6) 0.012(5) O7 0.049(5) 0.073(6) 0.050(5) -0.020(4) -0.017(4) 0.003(4) O8 0.045(5) 0.084(6) 0.060(6) -0.030(5) -0.011(4) 0.016(4) O9 0.31(4) 0.101(17) 0.066(16) -0.027(13) -0.041(19) 0.07(2) C1 0.063(9) 0.051(8) 0.053(8) 0.000(6) -0.017(7) -0.001(6) C2 0.078(11) 0.067(9) 0.082(11) -0.047(8) -0.012(8) 0.009(8) C3 0.087(11) 0.070(9) 0.042(8) -0.021(7) -0.007(7) 0.005(8) C4 0.054(9) 0.107(12) 0.027(7) -0.008(7) -0.007(6) -0.014(8) C5 0.049(8) 0.071(9) 0.026(6) -0.007(6) -0.007(5) -0.012(6) C6 0.050(8) 0.051(7) 0.035(7) -0.003(5) -0.009(6) -0.019(6) C7 0.056(9) 0.070(9) 0.046(8) 0.005(6) -0.017(6) 0.000(7) C8 0.089(12) 0.083(11) 0.063(10) 0.012(8) -0.022(9) -0.005(9) C9 0.102(14) 0.041(8) 0.111(14) 0.012(9) -0.004(11) -0.007(8) C10 0.095(13) 0.065(10) 0.075(11) -0.014(8) 0.001(9) -0.020(8) C11 0.041(7) 0.063(8) 0.034(7) -0.030(6) -0.004(5) -0.011(6) C12 0.036(7) 0.057(7) 0.027(6) -0.025(5) -0.015(5) 0.013(5) C13 0.028(6) 0.066(8) 0.040(7) -0.023(6) -0.016(5) 0.009(5) C14 0.043(7) 0.044(6) 0.034(6) -0.016(5) -0.013(5) -0.001(5) C15 0.031(7) 0.062(7) 0.053(7) -0.024(6) -0.023(5) 0.013(5) C16 0.039(7) 0.055(7) 0.061(8) -0.033(6) -0.024(6) 0.007(5) C17 0.037(7) 0.069(8) 0.048(7) -0.020(6) -0.018(6) 0.001(6) C18 0.069(9) 0.069(9) 0.047(8) -0.028(7) -0.030(7) -0.004(7) C19 0.065(9) 0.049(7) 0.033(7) 0.010(5) -0.017(6) -0.023(6) C20 0.039(7) 0.031(6) 0.028(6) 0.001(4) -0.012(5) -0.005(5) C21 0.057(9) 0.067(8) 0.048(8) -0.010(6) -0.008(6) -0.024(7) C22 0.049(8) 0.059(7) 0.044(7) -0.011(6) -0.024(6) -0.004(6) C23 0.040(7) 0.062(7) 0.035(6) 0.005(5) -0.019(5) -0.015(6) C24 0.042(7) 0.047(7) 0.045(7) 0.004(5) -0.011(5) -0.006(5) C25 0.037(7) 0.049(7) 0.059(8) -0.010(6) -0.019(6) 0.003(5) C26 0.040(7) 0.050(7) 0.030(6) -0.004(5) -0.013(5) -0.006(5) C27 0.028(6) 0.045(7) 0.049(7) -0.007(5) -0.012(5) 0.006(5) C28 0.039(7) 0.054(7) 0.057(8) 0.000(6) -0.025(6) -0.009(6) C29 0.049(8) 0.045(7) 0.035(7) 0.003(5) -0.014(6) -0.013(6) C30 0.083(11) 0.055(8) 0.050(8) -0.006(6) -0.008(7) 0.011(7) C31 0.091(12) 0.064(9) 0.100(13) -0.048(9) -0.021(10) 0.013(8) C32 0.081(11) 0.084(11) 0.058(10) -0.031(8) -0.009(8) 0.018(8) C33 0.081(11) 0.072(9) 0.053(9) -0.029(7) -0.014(7) 0.008(8) C34 0.045(8) 0.058(8) 0.051(8) -0.024(6) -0.011(6) 0.006(6) C35 0.036(7) 0.052(7) 0.037(7) -0.005(5) -0.011(5) -0.010(5) C36 0.064(9) 0.071(9) 0.034(7) -0.004(6) -0.008(6) -0.013(7) C37 0.078(10) 0.054(8) 0.043(8) 0.012(6) -0.005(7) -0.002(7) C38 0.076(10) 0.041(7) 0.067(9) 0.004(6) -0.015(8) -0.005(7) C39 0.053(8) 0.047(7) 0.046(7) -0.009(6) -0.011(6) 0.005(6) C40 0.033(7) 0.045(7) 0.045(7) 0.000(5) -0.003(6) -0.013(5) C41 0.070(9) 0.070(8) 0.037(7) -0.010(6) 0.002(6) -0.027(7) C42 0.064(9) 0.073(8) 0.023(6) -0.019(6) -0.008(5) -0.017(7) C43 0.047(7) 0.030(6) 0.031(6) -0.009(4) -0.007(5) -0.006(5) C44 0.052(8) 0.054(7) 0.049(7) -0.019(6) -0.022(6) -0.008(6) C45 0.043(7) 0.065(8) 0.040(7) -0.013(6) -0.008(5) 0.001(6) C46 0.038(7) 0.056(7) 0.054(8) -0.022(6) -0.007(6) 0.000(6) _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 O3 1.958(7) . ? Zn1 O1 2.036(7) . ? Zn1 N5 2.081(9) . ? Zn1 N4 2.159(9) . ? Zn1 N6 2.164(9) . ? Zn2 O5 1.977(7) . ? Zn2 O7 2.021(8) . ? Zn2 N2 2.089(9) . ? Zn2 N1 2.165(9) . ? Zn2 N3 2.165(9) . ? N1 C6 1.300(12) . ? N1 C10 1.331(15) . ? N2 C5 1.338(13) . ? N2 C1 1.352(14) . ? N3 C22 1.343(13) . ? N3 C18 1.345(13) . ? N4 C45 1.350(13) . ? N4 C41 1.355(13) . ? N5 C35 1.333(12) . ? N5 C39 1.346(13) . ? N6 C34 1.305(13) . ? N6 C30 1.336(14) . ? O1 C29 1.278(12) . ? O2 C29 1.209(12) . ? O3 C40 1.289(13) . ? O4 C40 1.173(12) . ? O5 C12 1.254(12) . ? O6 C12 1.236(11) . ? O7 C11 1.259(12) . ? O8 C11 1.216(11) . ? C1 C2 1.375(15) . ? C1 H1 0.9300 . ? C2 C3 1.370(17) . ? C2 H2 0.9300 . ? C3 C4 1.376(17) . ? C3 H3 0.9300 . ? C4 C5 1.379(14) . ? C4 H4 0.9300 . ? C5 C6 1.465(16) . ? C6 C7 1.388(14) . ? C7 C8 1.377(18) . ? C7 H7 0.9300 . ? C8 C9 1.382(19) . ? C8 H8 0.9300 . ? C9 C10 1.377(18) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C15 1.501(14) 1_455 ? C12 C13 1.513(14) . ? C13 C14 1.364(14) . ? C13 C17 1.365(13) . ? C14 C15 1.385(14) . ? C14 H14 0.9300 . ? C15 C16 1.383(13) . ? C15 C11 1.501(14) 1_655 ? C16 C46 1.412(14) 1_565 ? C16 H16 0.9300 . ? C17 C46 1.388(15) 1_565 ? C17 H17 0.9300 . ? C18 C19 1.326(14) . ? C18 H18 0.9300 . ? C19 C20 1.405(13) . ? C19 H19 0.9300 . ? C20 C21 1.364(14) . ? C20 C23 1.474(13) . ? C21 C22 1.406(15) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.363(14) . ? C23 C28 1.401(15) . ? C24 C25 1.372(14) . ? C24 H24 0.9300 . ? C25 C26 1.386(15) . ? C25 C40 1.529(14) 1_455 ? C26 C27 1.418(13) . ? C26 H26 0.9300 . ? C27 C28 1.382(14) . ? C27 C29 1.509(15) . ? C28 H28 0.9300 . ? C30 C31 1.369(16) . ? C30 H30 0.9300 . ? C31 C32 1.373(18) . ? C31 H31 0.9300 . ? C32 C33 1.361(17) . ? C32 H32 0.9300 . ? C33 C34 1.378(14) . ? C33 H33 0.9300 . ? C34 C35 1.486(15) . ? C35 C36 1.371(14) . ? C36 C37 1.381(16) . ? C36 H36 0.9300 . ? C37 C38 1.352(16) . ? C37 H37 0.9300 . ? C38 C39 1.338(15) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 C25 1.529(14) 1_655 ? C41 C42 1.342(14) . ? C41 H41 0.9300 . ? C42 C43 1.395(13) . ? C42 H42 0.9300 . ? C43 C44 1.376(14) . ? C43 C46 1.468(13) . ? C44 C45 1.391(14) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C17 1.388(15) 1_545 ? C46 C16 1.412(14) 1_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Zn1 O1 108.5(3) . . ? O3 Zn1 N5 117.4(3) . . ? O1 Zn1 N5 132.4(3) . . ? O3 Zn1 N4 95.6(3) . . ? O1 Zn1 N4 89.0(3) . . ? N5 Zn1 N4 97.8(3) . . ? O3 Zn1 N6 95.9(3) . . ? O1 Zn1 N6 88.4(3) . . ? N5 Zn1 N6 75.8(3) . . ? N4 Zn1 N6 168.4(4) . . ? O5 Zn2 O7 109.1(3) . . ? O5 Zn2 N2 114.8(3) . . ? O7 Zn2 N2 134.4(3) . . ? O5 Zn2 N1 97.3(3) . . ? O7 Zn2 N1 87.8(4) . . ? N2 Zn2 N1 75.3(4) . . ? O5 Zn2 N3 95.9(3) . . ? O7 Zn2 N3 89.2(3) . . ? N2 Zn2 N3 97.8(3) . . ? N1 Zn2 N3 166.8(4) . . ? C6 N1 C10 119.3(11) . . ? C6 N1 Zn2 116.6(8) . . ? C10 N1 Zn2 124.1(8) . . ? C5 N2 C1 119.6(10) . . ? C5 N2 Zn2 117.0(8) . . ? C1 N2 Zn2 123.4(8) . . ? C22 N3 C18 117.4(10) . . ? C22 N3 Zn2 124.8(8) . . ? C18 N3 Zn2 117.2(8) . . ? C45 N4 C41 116.6(9) . . ? C45 N4 Zn1 125.6(7) . . ? C41 N4 Zn1 117.5(7) . . ? C35 N5 C39 117.4(9) . . ? C35 N5 Zn1 118.0(7) . . ? C39 N5 Zn1 124.5(7) . . ? C34 N6 C30 119.4(10) . . ? C34 N6 Zn1 115.7(7) . . ? C30 N6 Zn1 124.8(8) . . ? C29 O1 Zn1 105.8(7) . . ? C40 O3 Zn1 114.0(7) . . ? C12 O5 Zn2 116.3(7) . . ? C11 O7 Zn2 107.6(7) . . ? N2 C1 C2 122.8(12) . . ? N2 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 117.4(12) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C2 C3 C4 120.1(11) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.2(12) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N2 C5 C4 119.9(11) . . ? N2 C5 C6 116.1(10) . . ? C4 C5 C6 124.0(11) . . ? N1 C6 C7 122.3(11) . . ? N1 C6 C5 114.8(10) . . ? C7 C6 C5 122.9(11) . . ? C8 C7 C6 119.3(12) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 117.8(13) . . ? C7 C8 H8 121.1 . . ? C9 C8 H8 121.1 . . ? C10 C9 C8 119.1(14) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N1 C10 C9 122.2(14) . . ? N1 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? O8 C11 O7 123.3(11) . . ? O8 C11 C15 119.7(10) . 1_455 ? O7 C11 C15 116.9(9) . 1_455 ? O6 C12 O5 124.9(10) . . ? O6 C12 C13 117.6(10) . . ? O5 C12 C13 117.4(9) . . ? C14 C13 C17 121.2(10) . . ? C14 C13 C12 119.3(9) . . ? C17 C13 C12 119.5(9) . . ? C13 C14 C15 120.8(9) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 118.8(10) . . ? C16 C15 C11 120.4(9) . 1_655 ? C14 C15 C11 120.7(9) . 1_655 ? C15 C16 C46 120.5(10) . 1_565 ? C15 C16 H16 119.8 . . ? C46 C16 H16 119.8 1_565 . ? C13 C17 C46 120.0(11) . 1_565 ? C13 C17 H17 120.0 . . ? C46 C17 H17 120.0 1_565 . ? C19 C18 N3 123.7(11) . . ? C19 C18 H18 118.2 . . ? N3 C18 H18 118.2 . . ? C18 C19 C20 119.7(11) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 118.6(9) . . ? C21 C20 C23 121.7(9) . . ? C19 C20 C23 119.7(9) . . ? C20 C21 C22 118.2(10) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? N3 C22 C21 122.3(10) . . ? N3 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C24 C23 C28 117.7(10) . . ? C24 C23 C20 125.4(10) . . ? C28 C23 C20 116.8(9) . . ? C23 C24 C25 123.0(11) . . ? C23 C24 H24 118.5 . . ? C25 C24 H24 118.5 . . ? C24 C25 C26 120.2(10) . . ? C24 C25 C40 123.3(10) . 1_455 ? C26 C25 C40 116.5(10) . 1_455 ? C25 C26 C27 117.8(10) . . ? C25 C26 H26 121.1 . . ? C27 C26 H26 121.1 . . ? C28 C27 C26 120.4(10) . . ? C28 C27 C29 120.4(9) . . ? C26 C27 C29 119.0(9) . . ? C27 C28 C23 120.7(10) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? O2 C29 O1 125.8(11) . . ? O2 C29 C27 119.1(10) . . ? O1 C29 C27 115.1(9) . . ? N6 C30 C31 121.4(12) . . ? N6 C30 H30 119.3 . . ? C31 C30 H30 119.3 . . ? C30 C31 C32 118.4(12) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? C33 C32 C31 120.3(12) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 117.5(13) . . ? C32 C33 H33 121.2 . . ? C34 C33 H33 121.2 . . ? N6 C34 C33 123.0(11) . . ? N6 C34 C35 115.5(9) . . ? C33 C34 C35 121.5(11) . . ? N5 C35 C36 121.2(10) . . ? N5 C35 C34 114.8(9) . . ? C36 C35 C34 124.0(10) . . ? C35 C36 C37 120.4(11) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C38 C37 C36 117.4(11) . . ? C38 C37 H37 121.3 . . ? C36 C37 H37 121.3 . . ? C39 C38 C37 120.2(12) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C38 C39 N5 123.4(11) . . ? C38 C39 H39 118.3 . . ? N5 C39 H39 118.3 . . ? O4 C40 O3 126.0(10) . . ? O4 C40 C25 119.8(11) . 1_655 ? O3 C40 C25 114.1(10) . 1_655 ? C42 C41 N4 123.9(11) . . ? C42 C41 H41 118.0 . . ? N4 C41 H41 118.0 . . ? C41 C42 C43 119.9(10) . . ? C41 C42 H42 120.1 . . ? C43 C42 H42 120.1 . . ? C44 C43 C42 117.5(9) . . ? C44 C43 C46 122.0(9) . . ? C42 C43 C46 120.5(9) . . ? C43 C44 C45 119.7(10) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? N4 C45 C44 122.3(10) . . ? N4 C45 H45 118.8 . . ? C44 C45 H45 118.8 . . ? C17 C46 C16 118.7(10) 1_545 1_545 ? C17 C46 C43 123.8(10) 1_545 . ? C16 C46 C43 117.4(10) 1_545 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Zn2 N1 C6 117.1(8) . . . . ? O7 Zn2 N1 C6 -134.0(8) . . . . ? N2 Zn2 N1 C6 3.3(8) . . . . ? N3 Zn2 N1 C6 -57(2) . . . . ? O5 Zn2 N1 C10 -65.1(11) . . . . ? O7 Zn2 N1 C10 43.9(11) . . . . ? N2 Zn2 N1 C10 -178.9(12) . . . . ? N3 Zn2 N1 C10 121.0(16) . . . . ? O5 Zn2 N2 C5 -94.0(8) . . . . ? O7 Zn2 N2 C5 69.2(9) . . . . ? N1 Zn2 N2 C5 -2.6(8) . . . . ? N3 Zn2 N2 C5 165.8(8) . . . . ? O5 Zn2 N2 C1 83.9(10) . . . . ? O7 Zn2 N2 C1 -112.9(10) . . . . ? N1 Zn2 N2 C1 175.3(10) . . . . ? N3 Zn2 N2 C1 -16.2(10) . . . . ? O5 Zn2 N3 C22 -165.5(9) . . . . ? O7 Zn2 N3 C22 85.5(9) . . . . ? N2 Zn2 N3 C22 -49.4(9) . . . . ? N1 Zn2 N3 C22 8(2) . . . . ? O5 Zn2 N3 C18 24.1(9) . . . . ? O7 Zn2 N3 C18 -85.0(9) . . . . ? N2 Zn2 N3 C18 140.2(9) . . . . ? N1 Zn2 N3 C18 -161.9(14) . . . . ? O3 Zn1 N4 C45 166.9(9) . . . . ? O1 Zn1 N4 C45 -84.6(9) . . . . ? N5 Zn1 N4 C45 48.2(9) . . . . ? N6 Zn1 N4 C45 -7(2) . . . . ? O3 Zn1 N4 C41 -20.4(9) . . . . ? O1 Zn1 N4 C41 88.1(9) . . . . ? N5 Zn1 N4 C41 -139.1(9) . . . . ? N6 Zn1 N4 C41 165.3(16) . . . . ? O3 Zn1 N5 C35 92.0(8) . . . . ? O1 Zn1 N5 C35 -71.6(8) . . . . ? N4 Zn1 N5 C35 -167.5(7) . . . . ? N6 Zn1 N5 C35 2.7(7) . . . . ? O3 Zn1 N5 C39 -84.8(9) . . . . ? O1 Zn1 N5 C39 111.5(9) . . . . ? N4 Zn1 N5 C39 15.7(9) . . . . ? N6 Zn1 N5 C39 -174.1(10) . . . . ? O3 Zn1 N6 C34 -120.9(9) . . . . ? O1 Zn1 N6 C34 130.7(9) . . . . ? N5 Zn1 N6 C34 -4.0(8) . . . . ? N4 Zn1 N6 C34 53(2) . . . . ? O3 Zn1 N6 C30 62.9(11) . . . . ? O1 Zn1 N6 C30 -45.6(11) . . . . ? N5 Zn1 N6 C30 179.7(11) . . . . ? N4 Zn1 N6 C30 -122.8(17) . . . . ? O3 Zn1 O1 C29 176.2(7) . . . . ? N5 Zn1 O1 C29 -19.1(9) . . . . ? N4 Zn1 O1 C29 80.6(7) . . . . ? N6 Zn1 O1 C29 -88.1(7) . . . . ? O1 Zn1 O3 C40 -173.6(7) . . . . ? N5 Zn1 O3 C40 19.0(8) . . . . ? N4 Zn1 O3 C40 -82.8(8) . . . . ? N6 Zn1 O3 C40 96.1(8) . . . . ? O7 Zn2 O5 C12 169.3(7) . . . . ? N2 Zn2 O5 C12 -23.3(9) . . . . ? N1 Zn2 O5 C12 -100.5(8) . . . . ? N3 Zn2 O5 C12 78.1(8) . . . . ? O5 Zn2 O7 C11 -178.0(7) . . . . ? N2 Zn2 O7 C11 18.1(10) . . . . ? N1 Zn2 O7 C11 85.0(8) . . . . ? N3 Zn2 O7 C11 -82.0(8) . . . . ? C5 N2 C1 C2 -2.8(19) . . . . ? Zn2 N2 C1 C2 179.3(9) . . . . ? N2 C1 C2 C3 2(2) . . . . ? C1 C2 C3 C4 0(2) . . . . ? C2 C3 C4 C5 1(2) . . . . ? C1 N2 C5 C4 2.9(17) . . . . ? Zn2 N2 C5 C4 -179.0(8) . . . . ? C1 N2 C5 C6 -176.2(10) . . . . ? Zn2 N2 C5 C6 1.9(13) . . . . ? C3 C4 C5 N2 -1.9(18) . . . . ? C3 C4 C5 C6 177.1(12) . . . . ? C10 N1 C6 C7 -1.4(18) . . . . ? Zn2 N1 C6 C7 176.6(9) . . . . ? C10 N1 C6 C5 178.7(11) . . . . ? Zn2 N1 C6 C5 -3.3(13) . . . . ? N2 C5 C6 N1 1.0(16) . . . . ? C4 C5 C6 N1 -178.1(11) . . . . ? N2 C5 C6 C7 -178.9(11) . . . . ? C4 C5 C6 C7 2.0(19) . . . . ? N1 C6 C7 C8 0.4(19) . . . . ? C5 C6 C7 C8 -179.7(12) . . . . ? C6 C7 C8 C9 0(2) . . . . ? C7 C8 C9 C10 1(2) . . . . ? C6 N1 C10 C9 2(2) . . . . ? Zn2 N1 C10 C9 -175.5(11) . . . . ? C8 C9 C10 N1 -2(2) . . . . ? Zn2 O7 C11 O8 3.3(14) . . . . ? Zn2 O7 C11 C15 179.8(8) . . . 1_455 ? Zn2 O5 C12 O6 3.1(15) . . . . ? Zn2 O5 C12 C13 -179.2(7) . . . . ? O6 C12 C13 C14 11.0(16) . . . . ? O5 C12 C13 C14 -166.8(10) . . . . ? O6 C12 C13 C17 -170.6(11) . . . . ? O5 C12 C13 C17 11.6(16) . . . . ? C17 C13 C14 C15 -1.5(17) . . . . ? C12 C13 C14 C15 176.8(10) . . . . ? C13 C14 C15 C16 0.6(17) . . . . ? C13 C14 C15 C11 178.2(10) . . . 1_655 ? C14 C15 C16 C46 -0.1(17) . . . 1_565 ? C11 C15 C16 C46 -177.7(10) 1_655 . . 1_565 ? C14 C13 C17 C46 2.0(17) . . . 1_565 ? C12 C13 C17 C46 -176.4(11) . . . 1_565 ? C22 N3 C18 C19 2.9(18) . . . . ? Zn2 N3 C18 C19 174.1(10) . . . . ? N3 C18 C19 C20 0.0(19) . . . . ? C18 C19 C20 C21 -2.2(17) . . . . ? C18 C19 C20 C23 177.9(11) . . . . ? C19 C20 C21 C22 1.4(17) . . . . ? C23 C20 C21 C22 -178.7(10) . . . . ? C18 N3 C22 C21 -3.6(16) . . . . ? Zn2 N3 C22 C21 -174.0(8) . . . . ? C20 C21 C22 N3 1.5(17) . . . . ? C21 C20 C23 C24 -45.0(17) . . . . ? C19 C20 C23 C24 135.0(12) . . . . ? C21 C20 C23 C28 129.9(12) . . . . ? C19 C20 C23 C28 -50.2(15) . . . . ? C28 C23 C24 C25 3.0(18) . . . . ? C20 C23 C24 C25 177.8(10) . . . . ? C23 C24 C25 C26 -3.1(18) . . . . ? C23 C24 C25 C40 175.9(10) . . . 1_455 ? C24 C25 C26 C27 1.4(16) . . . . ? C40 C25 C26 C27 -177.6(9) 1_455 . . . ? C25 C26 C27 C28 0.1(16) . . . . ? C25 C26 C27 C29 -175.7(10) . . . . ? C26 C27 C28 C23 0.0(17) . . . . ? C29 C27 C28 C23 175.7(10) . . . . ? C24 C23 C28 C27 -1.4(17) . . . . ? C20 C23 C28 C27 -176.7(10) . . . . ? Zn1 O1 C29 O2 3.4(14) . . . . ? Zn1 O1 C29 C27 -178.6(7) . . . . ? C28 C27 C29 O2 -176.5(11) . . . . ? C26 C27 C29 O2 -0.7(16) . . . . ? C28 C27 C29 O1 5.4(16) . . . . ? C26 C27 C29 O1 -178.8(9) . . . . ? C34 N6 C30 C31 -1(2) . . . . ? Zn1 N6 C30 C31 175.4(10) . . . . ? N6 C30 C31 C32 1(2) . . . . ? C30 C31 C32 C33 -1(2) . . . . ? C31 C32 C33 C34 0(2) . . . . ? C30 N6 C34 C33 0.5(19) . . . . ? Zn1 N6 C34 C33 -176.0(10) . . . . ? C30 N6 C34 C35 -178.9(11) . . . . ? Zn1 N6 C34 C35 4.6(13) . . . . ? C32 C33 C34 N6 0(2) . . . . ? C32 C33 C34 C35 179.0(12) . . . . ? C39 N5 C35 C36 -2.6(15) . . . . ? Zn1 N5 C35 C36 -179.6(8) . . . . ? C39 N5 C35 C34 175.8(10) . . . . ? Zn1 N5 C35 C34 -1.2(12) . . . . ? N6 C34 C35 N5 -2.4(15) . . . . ? C33 C34 C35 N5 178.3(11) . . . . ? N6 C34 C35 C36 176.0(11) . . . . ? C33 C34 C35 C36 -3.4(18) . . . . ? N5 C35 C36 C37 1.4(18) . . . . ? C34 C35 C36 C37 -176.9(11) . . . . ? C35 C36 C37 C38 1(2) . . . . ? C36 C37 C38 C39 -1(2) . . . . ? C37 C38 C39 N5 0(2) . . . . ? C35 N5 C39 C38 1.8(17) . . . . ? Zn1 N5 C39 C38 178.6(9) . . . . ? Zn1 O3 C40 O4 -3.3(16) . . . . ? Zn1 O3 C40 C25 -179.6(7) . . . 1_655 ? C45 N4 C41 C42 -1.5(19) . . . . ? Zn1 N4 C41 C42 -174.9(10) . . . . ? N4 C41 C42 C43 -2(2) . . . . ? C41 C42 C43 C44 4.1(18) . . . . ? C41 C42 C43 C46 -174.7(11) . . . . ? C42 C43 C44 C45 -2.9(17) . . . . ? C46 C43 C44 C45 175.9(10) . . . . ? C41 N4 C45 C44 2.7(17) . . . . ? Zn1 N4 C45 C44 175.5(8) . . . . ? C43 C44 C45 N4 -0.5(18) . . . . ? C44 C43 C46 C17 46.0(17) . . . 1_545 ? C42 C43 C46 C17 -135.4(13) . . . 1_545 ? C44 C43 C46 C16 -130.4(12) . . . 1_545 ? C42 C43 C46 C16 48.3(16) . . . 1_545 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 2.088 _refine_diff_density_min -1.191 _refine_diff_density_rms 0.145 _database_code_depnum_ccdc_archive 'CCDC 937599' ####################################################################### # # 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 ? _chemical_formula_sum 'C92 H60 Co4 N12 O17' _chemical_formula_weight 1841.24 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' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.220(15) _cell_length_b 13.41(2) _cell_length_c 15.08(2) _cell_angle_alpha 76.59(2) _cell_angle_beta 78.429(17) _cell_angle_gamma 86.24(2) _cell_volume 1969(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10877 _diffrn_reflns_av_R_equivalents 0.1007 _diffrn_reflns_av_sigmaI/netI 0.2691 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6781 _reflns_number_gt 2321 _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^)+(0.0988P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6781 _refine_ls_number_parameters 568 _refine_ls_number_restraints 1584 _refine_ls_R_factor_all 0.2603 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.2595 _refine_ls_wR_factor_gt 0.1816 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.869 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co -0.05940(13) 0.46524(12) 0.74486(9) 0.0462(5) Uani 1 1 d . . . Co2 Co 0.57142(13) 1.08488(11) 0.24873(9) 0.0479(5) Uani 1 1 d . . . N1 N -0.0625(8) 0.3315(8) 0.8538(6) 0.064(2) Uani 1 1 d U . . N2 N -0.1249(8) 0.5184(8) 0.8641(6) 0.0524(19) Uani 1 1 d U . . N3 N 0.6153(8) 1.0071(8) 0.1385(6) 0.062(2) Uani 1 1 d U . . N4 N 0.5685(8) 1.1996(8) 0.1317(6) 0.056(2) Uani 1 1 d U . . N5 N -0.0314(7) 0.6026(7) 0.6437(5) 0.0517(19) Uani 1 1 d U . . N6 N 0.5503(8) 0.1708(7) 0.3525(6) 0.054(2) Uani 1 1 d U . . O1 O -0.2960(6) 0.9857(6) 0.3114(5) 0.0618(19) Uani 1 1 d U . . O2 O -0.1862(7) 1.1210(6) 0.2217(5) 0.067(2) Uani 1 1 d U . . O3 O 0.3976(6) 1.0136(6) 0.3022(5) 0.0616(19) Uani 1 1 d U . . O4 O 0.2974(8) 1.1411(7) 0.2219(6) 0.098(3) Uani 1 1 d U . . O5 O 0.1098(6) 0.4030(6) 0.6786(5) 0.0604(18) Uani 1 1 d U . . O6 O 0.1722(6) 0.4973(6) 0.7620(5) 0.064(2) Uani 1 1 d U . . O7 O -0.2016(6) 0.4125(6) 0.6937(5) 0.0620(19) Uani 1 1 d U . . O8 O -0.3425(8) 0.5143(7) 0.7625(6) 0.082(2) Uani 1 1 d U . . O9 O 0.3146(17) 0.8144(14) 0.2275(12) 0.106(4) Uani 0.50 1 d PU . . C1 C 0.2956(11) 1.0597(10) 0.2772(8) 0.061(3) Uani 1 1 d U . . C2 C 0.1646(9) 1.0071(9) 0.3167(7) 0.055(2) Uani 1 1 d U . . C3 C 0.0533(9) 1.0454(9) 0.2802(7) 0.052(2) Uani 1 1 d U . . H3 H 0.0591 1.1049 0.2335 0.063 Uiso 1 1 calc R . . C4 C -0.0678(9) 0.9951(9) 0.3131(7) 0.053(2) Uani 1 1 d U . . C5 C -0.0749(9) 0.9075(8) 0.3829(7) 0.051(2) Uani 1 1 d U . . H5 H -0.1559 0.8740 0.4045 0.061 Uiso 1 1 calc R . . C6 C 0.0352(9) 0.8671(8) 0.4225(7) 0.048(2) Uani 1 1 d U . . C7 C 0.1539(9) 0.9188(9) 0.3880(7) 0.056(2) Uani 1 1 d U . . H7 H 0.2289 0.8940 0.4131 0.067 Uiso 1 1 calc R . . C8 C -0.1908(10) 1.0395(10) 0.2796(7) 0.051(2) Uani 1 1 d U . . C9 C 0.0166(9) 0.7776(9) 0.4974(7) 0.051(2) Uani 1 1 d U . . C10 C 0.0585(9) 0.7742(9) 0.5793(7) 0.053(2) Uani 1 1 d U . . H10 H 0.1025 0.8289 0.5877 0.064 Uiso 1 1 calc R . . C11 C 0.0326(9) 0.6860(9) 0.6489(7) 0.054(2) Uani 1 1 d U . . H11 H 0.0618 0.6838 0.7039 0.065 Uiso 1 1 calc R . . C12 C -0.0683(10) 0.6106(9) 0.5611(7) 0.057(2) Uani 1 1 d U . . H12 H -0.1144 0.5562 0.5542 0.068 Uiso 1 1 calc R . . C13 C -0.0439(10) 0.6894(9) 0.4894(7) 0.056(2) Uani 1 1 d U . . H13 H -0.0668 0.6868 0.4333 0.067 Uiso 1 1 calc R . . C14 C 0.1974(10) 0.4384(9) 0.7086(7) 0.053(2) Uani 1 1 d U . . C15 C 0.3399(9) 0.4099(8) 0.6760(7) 0.046(2) Uani 1 1 d U . . C16 C 0.4425(9) 0.4433(8) 0.7055(7) 0.052(2) Uani 1 1 d U . . H16 H 0.4228 0.4840 0.7489 0.062 Uiso 1 1 calc R . . C17 C 0.5737(10) 0.4199(8) 0.6746(7) 0.050(2) Uani 1 1 d U . . C18 C 0.6025(10) 0.3623(8) 0.6073(7) 0.054(2) Uani 1 1 d U . . H18 H 0.6911 0.3456 0.5856 0.065 Uiso 1 1 calc R . . C19 C 0.5025(9) 0.3291(8) 0.5716(7) 0.050(2) Uani 1 1 d U . . C20 C 0.3703(10) 0.3531(8) 0.6092(7) 0.055(2) Uani 1 1 d U . . H20 H 0.3010 0.3298 0.5882 0.066 Uiso 1 1 calc R . . C21 C 0.5256(9) 0.2710(8) 0.4997(7) 0.048(2) Uani 1 1 d U . . C22 C 0.4547(10) 0.1826(9) 0.5073(7) 0.056(2) Uani 1 1 d U . . H22 H 0.3973 0.1553 0.5627 0.067 Uiso 1 1 calc R . . C23 C 0.4686(10) 0.1369(9) 0.4359(7) 0.060(3) Uani 1 1 d U . . H23 H 0.4195 0.0784 0.4437 0.072 Uiso 1 1 calc R . . C24 C 0.6238(10) 0.2508(9) 0.3482(7) 0.057(3) Uani 1 1 d U . . H24 H 0.6864 0.2729 0.2942 0.068 Uiso 1 1 calc R . . C25 C 0.6141(9) 0.3038(8) 0.4181(7) 0.052(2) Uani 1 1 d U . . H25 H 0.6667 0.3605 0.4099 0.062 Uiso 1 1 calc R . . C26 C -0.0291(11) 0.2373(11) 0.8412(9) 0.077(3) Uani 1 1 d U . . H26 H -0.0115 0.2268 0.7810 0.093 Uiso 1 1 calc R . . C27 C -0.0196(12) 0.1541(11) 0.9146(10) 0.088(3) Uani 1 1 d U . . H27 H 0.0059 0.0890 0.9050 0.105 Uiso 1 1 calc R . . C28 C -0.0498(12) 0.1732(12) 1.0016(10) 0.086(3) Uani 1 1 d U . . H28 H -0.0473 0.1186 1.0522 0.103 Uiso 1 1 calc R . . C29 C -0.0832(11) 0.2675(11) 1.0179(9) 0.078(3) Uani 1 1 d U . . H29 H -0.1014 0.2796 1.0774 0.093 Uiso 1 1 calc R . . C30 C -0.0884(10) 0.3448(10) 0.9397(8) 0.063(2) Uani 1 1 d U . . C31 C -0.1271(10) 0.4491(10) 0.9448(8) 0.062(2) Uani 1 1 d U . . C32 C -0.1706(10) 0.4828(10) 1.0287(8) 0.066(3) Uani 1 1 d U . . H32 H -0.1725 0.4368 1.0855 0.079 Uiso 1 1 calc R . . C33 C -0.2091(11) 0.5814(11) 1.0262(9) 0.073(3) Uani 1 1 d U . . H33 H -0.2348 0.6030 1.0815 0.088 Uiso 1 1 calc R . . C34 C -0.2111(10) 0.6491(10) 0.9452(8) 0.066(3) Uani 1 1 d U . . H34 H -0.2400 0.7166 0.9435 0.080 Uiso 1 1 calc R . . C35 C -0.1684(10) 0.6140(10) 0.8648(8) 0.064(3) Uani 1 1 d U . . H35 H -0.1701 0.6596 0.8082 0.077 Uiso 1 1 calc R . . C36 C 0.6340(11) 0.9046(11) 0.1501(9) 0.076(3) Uani 1 1 d U . . H36 H 0.6190 0.8625 0.2095 0.091 Uiso 1 1 calc R . . C37 C 0.6754(12) 0.8628(11) 0.0739(9) 0.080(3) Uani 1 1 d U . . H37 H 0.6897 0.7923 0.0822 0.096 Uiso 1 1 calc R . . C38 C 0.6957(12) 0.9224(11) -0.0129(9) 0.081(3) Uani 1 1 d U . . H38 H 0.7256 0.8939 -0.0642 0.097 Uiso 1 1 calc R . . C39 C 0.6709(11) 1.0280(11) -0.0241(9) 0.075(3) Uani 1 1 d U . . H39 H 0.6811 1.0711 -0.0829 0.090 Uiso 1 1 calc R . . C40 C 0.6320(10) 1.0653(10) 0.0527(8) 0.061(2) Uani 1 1 d U . . C41 C 0.6017(10) 1.1733(10) 0.0501(8) 0.059(2) Uani 1 1 d U . . C42 C 0.6014(10) 1.2461(10) -0.0325(8) 0.068(3) Uani 1 1 d U . . H42 H 0.6235 1.2274 -0.0895 0.081 Uiso 1 1 calc R . . C43 C 0.5677(11) 1.3465(10) -0.0281(9) 0.074(3) Uani 1 1 d U . . H43 H 0.5694 1.3974 -0.0820 0.089 Uiso 1 1 calc R . . C44 C 0.5321(11) 1.3695(10) 0.0568(8) 0.076(3) Uani 1 1 d U . . H44 H 0.5071 1.4364 0.0612 0.091 Uiso 1 1 calc R . . C45 C 0.5325(11) 1.2971(10) 0.1336(8) 0.067(3) Uani 1 1 d U . . H45 H 0.5070 1.3148 0.1908 0.081 Uiso 1 1 calc R . . C49 C -0.3141(11) 0.4502(10) 0.7131(8) 0.058(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 Co1 0.0380(8) 0.0652(12) 0.0356(9) -0.0096(7) -0.0080(7) -0.0046(7) Co2 0.0415(9) 0.0554(11) 0.0464(9) -0.0076(8) -0.0126(7) 0.0004(8) N1 0.049(4) 0.081(5) 0.058(4) -0.009(4) -0.007(4) -0.011(4) N2 0.041(4) 0.077(5) 0.043(4) -0.014(4) -0.012(3) -0.013(4) N3 0.056(4) 0.072(5) 0.063(4) -0.014(4) -0.022(4) -0.001(4) N4 0.039(4) 0.075(5) 0.056(4) -0.014(4) -0.015(4) -0.003(4) N5 0.047(4) 0.070(4) 0.043(4) -0.016(4) -0.011(3) -0.010(4) N6 0.042(4) 0.066(5) 0.052(5) -0.007(4) -0.010(4) -0.013(4) O1 0.038(4) 0.079(5) 0.068(4) -0.010(4) -0.017(3) -0.002(4) O2 0.054(4) 0.078(6) 0.059(5) 0.008(4) -0.019(4) 0.008(4) O3 0.038(4) 0.082(5) 0.065(4) -0.013(4) -0.013(3) -0.005(3) O4 0.064(5) 0.102(7) 0.107(6) 0.017(6) -0.014(5) -0.015(5) O5 0.043(3) 0.083(4) 0.056(4) -0.015(3) -0.010(3) 0.000(3) O6 0.049(4) 0.081(5) 0.065(5) -0.025(4) -0.011(4) 0.013(4) O7 0.033(3) 0.091(5) 0.062(4) -0.010(4) -0.017(3) -0.001(4) O8 0.074(5) 0.105(7) 0.083(6) -0.030(5) -0.038(4) -0.009(5) O9 0.108(7) 0.107(8) 0.089(7) -0.012(7) -0.005(7) 0.020(7) C1 0.041(5) 0.079(6) 0.057(5) -0.004(5) -0.013(4) 0.001(5) C2 0.037(4) 0.075(5) 0.055(5) -0.014(4) -0.014(4) -0.007(4) C3 0.038(4) 0.073(5) 0.049(5) -0.014(4) -0.015(4) -0.003(4) C4 0.036(4) 0.071(5) 0.053(5) -0.015(4) -0.012(4) -0.004(4) C5 0.036(4) 0.069(5) 0.048(4) -0.013(4) -0.011(4) -0.006(4) C6 0.034(4) 0.068(5) 0.043(4) -0.008(4) -0.013(4) -0.004(4) C7 0.038(4) 0.074(5) 0.059(5) -0.011(4) -0.018(4) -0.007(4) C8 0.039(5) 0.074(6) 0.044(5) -0.016(5) -0.016(4) -0.003(5) C9 0.044(4) 0.070(5) 0.042(4) -0.010(4) -0.012(4) -0.008(4) C10 0.043(5) 0.072(5) 0.048(5) -0.012(4) -0.017(4) -0.011(4) C11 0.049(4) 0.074(5) 0.044(4) -0.013(4) -0.017(4) -0.010(4) C12 0.053(5) 0.066(5) 0.052(5) -0.010(4) -0.012(4) -0.013(4) C13 0.054(5) 0.073(6) 0.043(5) -0.007(5) -0.017(4) -0.012(5) C14 0.044(4) 0.071(5) 0.046(5) -0.017(4) -0.008(4) -0.012(4) C15 0.032(4) 0.069(5) 0.041(5) -0.012(4) -0.013(4) -0.008(4) C16 0.039(5) 0.071(6) 0.048(5) -0.017(4) -0.013(4) 0.003(4) C17 0.041(5) 0.069(6) 0.044(5) -0.017(4) -0.015(4) -0.003(4) C18 0.041(4) 0.075(6) 0.046(5) -0.010(4) -0.013(4) -0.005(4) C19 0.037(4) 0.068(5) 0.047(4) -0.014(4) -0.011(4) -0.007(4) C20 0.040(4) 0.075(5) 0.055(5) -0.017(4) -0.016(4) -0.005(4) C21 0.036(4) 0.066(5) 0.048(5) -0.017(4) -0.012(4) -0.011(4) C22 0.052(5) 0.065(6) 0.049(5) -0.012(5) -0.005(4) -0.011(5) C23 0.052(5) 0.069(6) 0.056(6) -0.012(5) -0.004(5) -0.019(5) C24 0.045(5) 0.070(6) 0.053(5) -0.009(5) -0.006(4) -0.007(5) C25 0.045(5) 0.067(5) 0.049(5) -0.018(4) -0.011(4) -0.016(4) C26 0.058(5) 0.094(6) 0.067(5) -0.003(5) 0.002(5) -0.012(5) C27 0.075(6) 0.085(7) 0.091(7) 0.006(6) -0.011(6) -0.013(6) C28 0.073(6) 0.094(7) 0.078(6) 0.008(6) -0.015(6) -0.009(6) C29 0.062(5) 0.098(6) 0.065(5) 0.000(5) -0.009(5) -0.015(5) C30 0.045(4) 0.087(5) 0.056(5) -0.005(5) -0.014(4) -0.023(5) C31 0.047(4) 0.093(6) 0.052(5) -0.013(5) -0.017(4) -0.021(5) C32 0.055(5) 0.091(6) 0.054(5) -0.010(5) -0.019(4) -0.015(5) C33 0.061(6) 0.099(7) 0.063(6) -0.025(6) -0.008(5) -0.015(6) C34 0.062(6) 0.087(7) 0.062(6) -0.033(5) -0.018(5) -0.011(5) C35 0.054(5) 0.087(6) 0.054(5) -0.021(5) -0.009(4) -0.010(5) C36 0.074(5) 0.087(6) 0.073(5) -0.022(5) -0.023(5) 0.005(5) C37 0.084(6) 0.079(7) 0.082(7) -0.032(6) -0.015(6) 0.005(6) C38 0.083(6) 0.089(7) 0.075(6) -0.030(6) -0.013(6) 0.000(6) C39 0.071(5) 0.087(6) 0.070(5) -0.021(5) -0.015(5) -0.003(5) C40 0.050(5) 0.086(6) 0.055(5) -0.023(5) -0.017(4) -0.005(5) C41 0.048(4) 0.081(5) 0.054(5) -0.012(5) -0.023(4) -0.008(5) C42 0.059(5) 0.087(6) 0.057(5) -0.010(5) -0.018(5) -0.006(5) C43 0.065(6) 0.089(7) 0.061(6) 0.000(6) -0.017(5) -0.001(6) C44 0.071(6) 0.082(7) 0.066(6) 0.000(6) -0.012(6) -0.004(6) C45 0.058(5) 0.085(7) 0.055(5) -0.004(5) -0.013(5) -0.005(6) C49 0.050(5) 0.075(6) 0.052(6) -0.015(5) -0.010(5) -0.016(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 Co1 O7 2.010(7) . ? Co1 O5 2.047(7) . ? Co1 N2 2.059(9) . ? Co1 N5 2.096(9) . ? Co1 N1 2.130(10) . ? Co2 O3 2.003(7) . ? Co2 O1 2.048(7) 1_655 ? Co2 N4 2.058(9) . ? Co2 N6 2.119(9) 1_565 ? Co2 N3 2.121(10) . ? N1 C30 1.320(13) . ? N1 C26 1.333(14) . ? N2 C35 1.331(13) . ? N2 C31 1.346(13) . ? N3 C40 1.332(13) . ? N3 C36 1.350(14) . ? N4 C41 1.331(13) . ? N4 C45 1.341(14) . ? N5 C12 1.351(11) . ? N5 C11 1.357(12) . ? N6 C24 1.333(12) . ? N6 C23 1.359(12) . ? N6 Co2 2.119(9) 1_545 ? O1 C8 1.281(11) . ? O1 Co2 2.048(7) 1_455 ? O2 C8 1.227(12) . ? O3 C1 1.255(12) . ? O4 C1 1.209(13) . ? O5 C14 1.245(11) . ? O6 C14 1.234(11) . ? O7 C49 1.233(12) . ? O8 C49 1.246(12) . ? C1 C2 1.502(14) . ? C2 C3 1.380(13) . ? C2 C7 1.397(14) . ? C3 C4 1.393(13) . ? C3 H3 0.9300 . ? C4 C5 1.379(14) . ? C4 C8 1.485(13) . ? C5 C6 1.399(12) . ? C5 H5 0.9300 . ? C6 C7 1.383(13) . ? C6 C9 1.437(13) . ? C7 H7 0.9300 . ? C9 C10 1.376(12) . ? C9 C13 1.410(14) . ? C10 C11 1.387(13) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.322(13) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.495(13) . ? C15 C16 1.356(12) . ? C15 C20 1.375(13) . ? C16 C17 1.369(12) . ? C16 H16 0.9300 . ? C17 C18 1.388(13) . ? C17 C49 1.502(13) 1_655 ? C18 C19 1.387(12) . ? C18 H18 0.9300 . ? C19 C20 1.404(12) . ? C19 C21 1.451(13) . ? C20 H20 0.9300 . ? C21 C25 1.371(12) . ? C21 C22 1.400(13) . ? C22 C23 1.338(13) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.386(13) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.392(16) . ? C26 H26 0.9300 . ? C27 C28 1.365(16) . ? C27 H27 0.9300 . ? C28 C29 1.353(16) . ? C28 H28 0.9300 . ? C29 C30 1.385(16) . ? C29 H29 0.9300 . ? C30 C31 1.444(16) . ? C31 C32 1.420(14) . ? C32 C33 1.349(15) . ? C32 H32 0.9300 . ? C33 C34 1.344(15) . ? C33 H33 0.9300 . ? C34 C35 1.382(14) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C37 1.374(15) . ? C36 H36 0.9300 . ? C37 C38 1.350(16) . ? C37 H37 0.9300 . ? C38 C39 1.398(16) . ? C38 H38 0.9300 . ? C39 C40 1.344(14) . ? C39 H39 0.9300 . ? C40 C41 1.454(15) . ? C41 C42 1.394(15) . ? C42 C43 1.382(15) . ? C42 H42 0.9300 . ? C43 C44 1.360(15) . ? C43 H43 0.9300 . ? C44 C45 1.327(15) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C49 C17 1.502(13) 1_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Co1 O5 101.4(3) . . ? O7 Co1 N2 115.7(3) . . ? O5 Co1 N2 139.1(3) . . ? O7 Co1 N5 95.6(3) . . ? O5 Co1 N5 90.6(3) . . ? N2 Co1 N5 101.5(4) . . ? O7 Co1 N1 92.7(3) . . ? O5 Co1 N1 86.4(3) . . ? N2 Co1 N1 75.9(4) . . ? N5 Co1 N1 171.6(3) . . ? O3 Co2 O1 102.4(3) . 1_655 ? O3 Co2 N4 114.6(3) . . ? O1 Co2 N4 139.8(3) 1_655 . ? O3 Co2 N6 94.1(3) . 1_565 ? O1 Co2 N6 90.9(3) 1_655 1_565 ? N4 Co2 N6 101.3(4) . 1_565 ? O3 Co2 N3 92.8(3) . . ? O1 Co2 N3 87.2(3) 1_655 . ? N4 Co2 N3 76.1(4) . . ? N6 Co2 N3 173.1(3) 1_565 . ? C30 N1 C26 118.0(12) . . ? C30 N1 Co1 117.1(9) . . ? C26 N1 Co1 124.7(8) . . ? C35 N2 C31 119.9(10) . . ? C35 N2 Co1 123.9(8) . . ? C31 N2 Co1 116.2(9) . . ? C40 N3 C36 119.1(11) . . ? C40 N3 Co2 116.5(9) . . ? C36 N3 Co2 124.3(8) . . ? C41 N4 C45 119.0(11) . . ? C41 N4 Co2 117.1(8) . . ? C45 N4 Co2 123.9(8) . . ? C12 N5 C11 113.7(9) . . ? C12 N5 Co1 120.1(7) . . ? C11 N5 Co1 125.9(7) . . ? C24 N6 C23 114.7(9) . . ? C24 N6 Co2 125.1(7) . 1_545 ? C23 N6 Co2 119.6(7) . 1_545 ? C8 O1 Co2 98.6(7) . 1_455 ? C1 O3 Co2 116.3(8) . . ? C14 O5 Co1 101.0(7) . . ? C49 O7 Co1 115.0(7) . . ? O4 C1 O3 124.3(11) . . ? O4 C1 C2 118.8(11) . . ? O3 C1 C2 116.9(11) . . ? C3 C2 C7 119.4(10) . . ? C3 C2 C1 119.3(11) . . ? C7 C2 C1 121.3(10) . . ? C2 C3 C4 120.1(11) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.1(10) . . ? C5 C4 C8 119.9(9) . . ? C3 C4 C8 120.8(11) . . ? C4 C5 C6 122.4(9) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C7 C6 C5 117.0(10) . . ? C7 C6 C9 124.8(9) . . ? C5 C6 C9 118.2(9) . . ? C6 C7 C2 122.0(10) . . ? C6 C7 H7 119.0 . . ? C2 C7 H7 119.0 . . ? O2 C8 O1 123.9(10) . . ? O2 C8 C4 120.0(10) . . ? O1 C8 C4 116.0(11) . . ? C10 C9 C13 117.4(10) . . ? C10 C9 C6 121.4(10) . . ? C13 C9 C6 121.3(9) . . ? C9 C10 C11 117.5(10) . . ? C9 C10 H10 121.3 . . ? C11 C10 H10 121.3 . . ? N5 C11 C10 125.7(9) . . ? N5 C11 H11 117.1 . . ? C10 C11 H11 117.1 . . ? C13 C12 N5 125.2(11) . . ? C13 C12 H12 117.4 . . ? N5 C12 H12 117.4 . . ? C12 C13 C9 120.3(10) . . ? C12 C13 H13 119.9 . . ? C9 C13 H13 119.9 . . ? O6 C14 O5 123.1(10) . . ? O6 C14 C15 118.9(9) . . ? O5 C14 C15 118.0(10) . . ? C16 C15 C20 118.0(10) . . ? C16 C15 C14 122.5(10) . . ? C20 C15 C14 119.4(9) . . ? C15 C16 C17 123.2(10) . . ? C15 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C16 C17 C18 118.0(9) . . ? C16 C17 C49 122.8(10) . 1_655 ? C18 C17 C49 119.1(10) . 1_655 ? C19 C18 C17 121.6(10) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 116.9(10) . . ? C18 C19 C21 124.5(9) . . ? C20 C19 C21 118.5(9) . . ? C15 C20 C19 122.2(9) . . ? C15 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C25 C21 C22 116.6(10) . . ? C25 C21 C19 121.0(10) . . ? C22 C21 C19 122.4(9) . . ? C23 C22 C21 120.8(10) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 N6 123.9(11) . . ? C22 C23 H23 118.1 . . ? N6 C23 H23 118.1 . . ? N6 C24 C25 125.0(10) . . ? N6 C24 H24 117.5 . . ? C25 C24 H24 117.5 . . ? C21 C25 C24 118.8(10) . . ? C21 C25 H25 120.6 . . ? C24 C25 H25 120.6 . . ? N1 C26 C27 122.4(13) . . ? N1 C26 H26 118.8 . . ? C27 C26 H26 118.8 . . ? C28 C27 C26 116.4(14) . . ? C28 C27 H27 121.8 . . ? C26 C27 H27 121.8 . . ? C29 C28 C27 123.2(14) . . ? C29 C28 H28 118.4 . . ? C27 C28 H28 118.4 . . ? C28 C29 C30 115.4(13) . . ? C28 C29 H29 122.3 . . ? C30 C29 H29 122.3 . . ? N1 C30 C29 124.5(13) . . ? N1 C30 C31 112.9(11) . . ? C29 C30 C31 122.6(12) . . ? N2 C31 C32 118.0(12) . . ? N2 C31 C30 117.4(11) . . ? C32 C31 C30 124.6(12) . . ? C33 C32 C31 120.1(12) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C34 C33 C32 121.4(13) . . ? C34 C33 H33 119.3 . . ? C32 C33 H33 119.3 . . ? C33 C34 C35 117.1(13) . . ? C33 C34 H34 121.4 . . ? C35 C34 H34 121.4 . . ? N2 C35 C34 123.4(12) . . ? N2 C35 H35 118.3 . . ? C34 C35 H35 118.3 . . ? N3 C36 C37 119.6(13) . . ? N3 C36 H36 120.2 . . ? C37 C36 H36 120.2 . . ? C38 C37 C36 121.0(14) . . ? C38 C37 H37 119.5 . . ? C36 C37 H37 119.5 . . ? C37 C38 C39 118.7(13) . . ? C37 C38 H38 120.7 . . ? C39 C38 H38 120.7 . . ? C40 C39 C38 118.1(13) . . ? C40 C39 H39 121.0 . . ? C38 C39 H39 121.0 . . ? N3 C40 C39 123.4(13) . . ? N3 C40 C41 113.3(11) . . ? C39 C40 C41 123.2(12) . . ? N4 C41 C42 120.8(12) . . ? N4 C41 C40 116.6(11) . . ? C42 C41 C40 122.6(12) . . ? C43 C42 C41 118.6(12) . . ? C43 C42 H42 120.7 . . ? C41 C42 H42 120.7 . . ? C44 C43 C42 118.6(13) . . ? C44 C43 H43 120.7 . . ? C42 C43 H43 120.7 . . ? C45 C44 C43 120.5(14) . . ? C45 C44 H44 119.8 . . ? C43 C44 H44 119.8 . . ? C44 C45 N4 122.5(12) . . ? C44 C45 H45 118.7 . . ? N4 C45 H45 118.7 . . ? O7 C49 O8 124.4(11) . . ? O7 C49 C17 119.3(11) . 1_455 ? O8 C49 C17 116.2(11) . 1_455 ? 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 O7 Co1 N1 C30 -122.5(8) . . . . ? O5 Co1 N1 C30 136.2(8) . . . . ? N2 Co1 N1 C30 -6.6(7) . . . . ? N5 Co1 N1 C30 67(3) . . . . ? O7 Co1 N1 C26 63.6(9) . . . . ? O5 Co1 N1 C26 -37.7(9) . . . . ? N2 Co1 N1 C26 179.4(10) . . . . ? N5 Co1 N1 C26 -107(2) . . . . ? O7 Co1 N2 C35 -86.8(8) . . . . ? O5 Co1 N2 C35 119.9(8) . . . . ? N5 Co1 N2 C35 15.3(9) . . . . ? N1 Co1 N2 C35 -173.0(9) . . . . ? O7 Co1 N2 C31 90.6(7) . . . . ? O5 Co1 N2 C31 -62.7(9) . . . . ? N5 Co1 N2 C31 -167.3(7) . . . . ? N1 Co1 N2 C31 4.5(7) . . . . ? O3 Co2 N3 C40 120.7(8) . . . . ? O1 Co2 N3 C40 -137.1(8) 1_655 . . . ? N4 Co2 N3 C40 6.0(7) . . . . ? N6 Co2 N3 C40 -62(3) 1_565 . . . ? O3 Co2 N3 C36 -63.1(9) . . . . ? O1 Co2 N3 C36 39.2(9) 1_655 . . . ? N4 Co2 N3 C36 -177.7(9) . . . . ? N6 Co2 N3 C36 114(3) 1_565 . . . ? O3 Co2 N4 C41 -90.9(8) . . . . ? O1 Co2 N4 C41 64.1(9) 1_655 . . . ? N6 Co2 N4 C41 169.3(7) 1_565 . . . ? N3 Co2 N4 C41 -4.2(7) . . . . ? O3 Co2 N4 C45 87.6(9) . . . . ? O1 Co2 N4 C45 -117.4(8) 1_655 . . . ? N6 Co2 N4 C45 -12.3(9) 1_565 . . . ? N3 Co2 N4 C45 174.3(9) . . . . ? O7 Co1 N5 C12 -21.5(8) . . . . ? O5 Co1 N5 C12 80.1(8) . . . . ? N2 Co1 N5 C12 -139.2(7) . . . . ? N1 Co1 N5 C12 149(2) . . . . ? O7 Co1 N5 C11 164.7(8) . . . . ? O5 Co1 N5 C11 -93.8(8) . . . . ? N2 Co1 N5 C11 46.9(8) . . . . ? N1 Co1 N5 C11 -25(3) . . . . ? O1 Co2 O3 C1 178.1(8) 1_655 . . . ? N4 Co2 O3 C1 -18.1(9) . . . . ? N6 Co2 O3 C1 86.2(8) 1_565 . . . ? N3 Co2 O3 C1 -94.2(8) . . . . ? O7 Co1 O5 C14 178.2(7) . . . . ? N2 Co1 O5 C14 -26.1(9) . . . . ? N5 Co1 O5 C14 82.4(7) . . . . ? N1 Co1 O5 C14 -89.7(7) . . . . ? O5 Co1 O7 C49 -170.6(8) . . . . ? N2 Co1 O7 C49 26.8(9) . . . . ? N5 Co1 O7 C49 -78.9(8) . . . . ? N1 Co1 O7 C49 102.5(8) . . . . ? Co2 O3 C1 O4 2.3(16) . . . . ? Co2 O3 C1 C2 179.9(7) . . . . ? O4 C1 C2 C3 8.5(17) . . . . ? O3 C1 C2 C3 -169.2(10) . . . . ? O4 C1 C2 C7 -173.0(11) . . . . ? O3 C1 C2 C7 9.3(17) . . . . ? C7 C2 C3 C4 -1.3(16) . . . . ? C1 C2 C3 C4 177.2(10) . . . . ? C2 C3 C4 C5 0.7(16) . . . . ? C2 C3 C4 C8 175.4(9) . . . . ? C3 C4 C5 C6 0.3(16) . . . . ? C8 C4 C5 C6 -174.5(9) . . . . ? C4 C5 C6 C7 -0.5(16) . . . . ? C4 C5 C6 C9 177.7(10) . . . . ? C5 C6 C7 C2 -0.2(16) . . . . ? C9 C6 C7 C2 -178.2(10) . . . . ? C3 C2 C7 C6 1.1(17) . . . . ? C1 C2 C7 C6 -177.4(10) . . . . ? Co2 O1 C8 O2 -5.9(12) 1_455 . . . ? Co2 O1 C8 C4 177.4(7) 1_455 . . . ? C5 C4 C8 O2 175.3(10) . . . . ? C3 C4 C8 O2 0.7(16) . . . . ? C5 C4 C8 O1 -7.8(15) . . . . ? C3 C4 C8 O1 177.5(9) . . . . ? C7 C6 C9 C10 48.5(16) . . . . ? C5 C6 C9 C10 -129.5(10) . . . . ? C7 C6 C9 C13 -130.7(11) . . . . ? C5 C6 C9 C13 51.3(14) . . . . ? C13 C9 C10 C11 -2.8(14) . . . . ? C6 C9 C10 C11 178.0(10) . . . . ? C12 N5 C11 C10 1.3(15) . . . . ? Co1 N5 C11 C10 175.5(8) . . . . ? C9 C10 C11 N5 -0.5(16) . . . . ? C11 N5 C12 C13 1.4(15) . . . . ? Co1 N5 C12 C13 -173.2(9) . . . . ? N5 C12 C13 C9 -4.8(18) . . . . ? C10 C9 C13 C12 5.3(15) . . . . ? C6 C9 C13 C12 -175.5(10) . . . . ? Co1 O5 C14 O6 -1.9(13) . . . . ? Co1 O5 C14 C15 179.8(8) . . . . ? O6 C14 C15 C16 2.5(16) . . . . ? O5 C14 C15 C16 -179.1(10) . . . . ? O6 C14 C15 C20 -173.3(10) . . . . ? O5 C14 C15 C20 5.2(16) . . . . ? C20 C15 C16 C17 -2.5(16) . . . . ? C14 C15 C16 C17 -178.3(10) . . . . ? C15 C16 C17 C18 2.4(16) . . . . ? C15 C16 C17 C49 -175.1(10) . . . 1_655 ? C16 C17 C18 C19 0.1(16) . . . . ? C49 C17 C18 C19 177.7(10) 1_655 . . . ? C17 C18 C19 C20 -2.3(15) . . . . ? C17 C18 C19 C21 178.4(10) . . . . ? C16 C15 C20 C19 0.1(16) . . . . ? C14 C15 C20 C19 176.1(10) . . . . ? C18 C19 C20 C15 2.2(16) . . . . ? C21 C19 C20 C15 -178.4(10) . . . . ? C18 C19 C21 C25 -51.2(16) . . . . ? C20 C19 C21 C25 129.5(11) . . . . ? C18 C19 C21 C22 132.3(11) . . . . ? C20 C19 C21 C22 -47.0(15) . . . . ? C25 C21 C22 C23 -3.6(16) . . . . ? C19 C21 C22 C23 173.1(10) . . . . ? C21 C22 C23 N6 0.2(18) . . . . ? C24 N6 C23 C22 4.1(16) . . . . ? Co2 N6 C23 C22 176.1(9) 1_545 . . . ? C23 N6 C24 C25 -5.2(15) . . . . ? Co2 N6 C24 C25 -176.7(8) 1_545 . . . ? C22 C21 C25 C24 2.5(15) . . . . ? C19 C21 C25 C24 -174.2(9) . . . . ? N6 C24 C25 C21 2.0(16) . . . . ? C30 N1 C26 C27 -0.6(17) . . . . ? Co1 N1 C26 C27 173.3(8) . . . . ? N1 C26 C27 C28 1.6(19) . . . . ? C26 C27 C28 C29 -2(2) . . . . ? C27 C28 C29 C30 1.6(19) . . . . ? C26 N1 C30 C29 0.1(16) . . . . ? Co1 N1 C30 C29 -174.3(8) . . . . ? C26 N1 C30 C31 -178.3(9) . . . . ? Co1 N1 C30 C31 7.3(12) . . . . ? C28 C29 C30 N1 -0.6(17) . . . . ? C28 C29 C30 C31 177.7(11) . . . . ? C35 N2 C31 C32 -3.0(14) . . . . ? Co1 N2 C31 C32 179.5(7) . . . . ? C35 N2 C31 C30 175.3(9) . . . . ? Co1 N2 C31 C30 -2.2(12) . . . . ? N1 C30 C31 N2 -3.4(14) . . . . ? C29 C30 C31 N2 178.1(9) . . . . ? N1 C30 C31 C32 174.8(9) . . . . ? C29 C30 C31 C32 -3.7(17) . . . . ? N2 C31 C32 C33 0.5(16) . . . . ? C30 C31 C32 C33 -177.7(10) . . . . ? C31 C32 C33 C34 1.9(17) . . . . ? C32 C33 C34 C35 -1.8(17) . . . . ? C31 N2 C35 C34 3.2(16) . . . . ? Co1 N2 C35 C34 -179.5(7) . . . . ? C33 C34 C35 N2 -0.8(17) . . . . ? C40 N3 C36 C37 2.8(17) . . . . ? Co2 N3 C36 C37 -173.4(8) . . . . ? N3 C36 C37 C38 -1.1(19) . . . . ? C36 C37 C38 C39 -1(2) . . . . ? C37 C38 C39 C40 2.1(18) . . . . ? C36 N3 C40 C39 -2.1(17) . . . . ? Co2 N3 C40 C39 174.3(9) . . . . ? C36 N3 C40 C41 176.9(9) . . . . ? Co2 N3 C40 C41 -6.7(12) . . . . ? C38 C39 C40 N3 -0.3(18) . . . . ? C38 C39 C40 C41 -179.2(10) . . . . ? C45 N4 C41 C42 1.0(15) . . . . ? Co2 N4 C41 C42 179.6(7) . . . . ? C45 N4 C41 C40 -176.4(9) . . . . ? Co2 N4 C41 C40 2.1(12) . . . . ? N3 C40 C41 N4 3.1(14) . . . . ? C39 C40 C41 N4 -177.9(10) . . . . ? N3 C40 C41 C42 -174.3(9) . . . . ? C39 C40 C41 C42 4.7(17) . . . . ? N4 C41 C42 C43 0.9(16) . . . . ? C40 C41 C42 C43 178.2(10) . . . . ? C41 C42 C43 C44 -2.1(17) . . . . ? C42 C43 C44 C45 1.4(18) . . . . ? C43 C44 C45 N4 0.5(18) . . . . ? C41 N4 C45 C44 -1.8(16) . . . . ? Co2 N4 C45 C44 179.8(8) . . . . ? Co1 O7 C49 O8 -1.9(16) . . . . ? Co1 O7 C49 C17 177.1(7) . . . 1_455 ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.692 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 937600' ####################################################################### # # 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 ? _chemical_formula_sum 'C H Co N O' _chemical_formula_weight 101.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.824(9) _cell_length_b 10.318(7) _cell_length_c 31.48(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.75 _cell_angle_gamma 90.00 _cell_volume 4079(5) _cell_formula_units_Z 51 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2499 _exptl_absorpt_coefficient_mu 5.094 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19362 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.1004 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6413 _reflns_number_gt 4057 _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^)+(0.0642P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6413 _refine_ls_number_parameters 595 _refine_ls_number_restraints 1650 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1424 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.858 _refine_ls_shift/su_max 0.010 _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 Co1 Co 0.92408(5) 0.60220(6) 0.131295(19) 0.03246(18) Uani 1 1 d . . . Co2 Co 0.54083(5) 0.14730(6) 0.371521(18) 0.03007(18) Uani 1 1 d . . . N1 N 1.0125(3) 0.6369(4) 0.08126(12) 0.0404(9) Uani 1 1 d U . . N2 N 0.8068(3) 0.5747(3) 0.07580(12) 0.0326(8) Uani 1 1 d U . . N3 N 0.6828(3) 0.1112(4) 0.41903(13) 0.0402(9) Uani 1 1 d U . . N4 N 0.4871(3) 0.1699(3) 0.42949(12) 0.0341(9) Uani 1 1 d U . . N5 N 0.3952(3) 0.1529(4) 0.32470(12) 0.0382(9) Uani 1 1 d U . . N6 N 0.8270(3) 0.5999(4) 0.17925(12) 0.0388(9) Uani 1 1 d U . . O1 O 0.9874(3) 0.4267(3) 0.14912(10) 0.0416(8) Uani 1 1 d U . . O2 O 0.8820(3) 0.2999(4) 0.10129(12) 0.0663(12) Uani 1 1 d U . . O3 O 1.0292(3) 0.7346(3) 0.17012(10) 0.0444(8) Uani 1 1 d U . . O4 O 0.8924(3) 0.8205(3) 0.12573(11) 0.0484(9) Uani 1 1 d U . . O5 O 0.6010(3) 0.0125(3) 0.33202(10) 0.0421(8) Uani 1 1 d U . . O6 O 0.5120(3) -0.0735(3) 0.37776(11) 0.0447(8) Uani 1 1 d U . . O7 O 0.5910(2) 0.3192(3) 0.35255(10) 0.0396(8) Uani 1 1 d U . . O8 O 0.5161(3) 0.4435(3) 0.39615(12) 0.0610(10) Uani 1 1 d U . . C1 C 0.9537(4) 0.3168(4) 0.13354(15) 0.0356(11) Uani 1 1 d U . . C2 C 1.0082(3) 0.1988(4) 0.15700(14) 0.0332(10) Uani 1 1 d U . . C3 C 1.0928(4) 0.2100(4) 0.19147(15) 0.0404(12) Uani 1 1 d U . . H3 H 1.1199 0.2921 0.1994 0.048 Uiso 1 1 calc R . . C4 C 0.9757(4) 0.8315(4) 0.15294(15) 0.0371(11) Uani 1 1 d U . . C5 C 1.0172(3) 0.9652(4) 0.16716(15) 0.0353(11) Uani 1 1 d U . . C6 C 0.9702(3) 1.0743(4) 0.14432(14) 0.0322(10) Uani 1 1 d U . . H6 H 0.9139 1.0640 0.1208 0.039 Uiso 1 1 calc R . . C7 C 1.0998(3) 0.9798(4) 0.20200(14) 0.0368(11) Uani 1 1 d U . . H7 H 1.1297 0.9070 0.2171 0.044 Uiso 1 1 calc R . . C8 C 1.1398(4) 1.1029(4) 0.21519(15) 0.0399(11) Uani 1 1 d U . . C9 C 1.2283(4) 1.1195(4) 0.25263(16) 0.0410(12) Uani 1 1 d U . . C10 C 1.3134(4) 1.2002(5) 0.25097(17) 0.0558(15) Uani 1 1 d U . . H10 H 1.3168 1.2437 0.2254 0.067 Uiso 1 1 calc R . . C11 C 1.2310(4) 1.0527(5) 0.29099(15) 0.0464(13) Uani 1 1 d U . . H11 H 1.1764 0.9955 0.2933 0.056 Uiso 1 1 calc R . . C12 C 0.7451(4) 0.6820(5) 0.17803(16) 0.0464(12) Uani 1 1 d U . . H12 H 0.7212 0.7287 0.1527 0.056 Uiso 1 1 calc R . . C13 C 0.6946(4) 0.7010(5) 0.21212(16) 0.0444(12) Uani 1 1 d U . . H13 H 0.6392 0.7604 0.2097 0.053 Uiso 1 1 calc R . . C14 C 0.7270(4) 0.6310(4) 0.25002(15) 0.0344(10) Uani 1 1 d U . . C15 C 0.8146(4) 0.5493(5) 0.25231(16) 0.0484(13) Uani 1 1 d U . . H15 H 0.8429 0.5053 0.2778 0.058 Uiso 1 1 calc R . . C16 C 0.8590(4) 0.5348(5) 0.21574(16) 0.0468(12) Uani 1 1 d U . . H16 H 0.9145 0.4759 0.2171 0.056 Uiso 1 1 calc R . . C17 C 0.6740(4) 0.6464(4) 0.28744(15) 0.0379(11) Uani 1 1 d U . . C18 C 0.6509(4) 0.5385(4) 0.31024(15) 0.0382(11) Uani 1 1 d U . . H18 H 0.6726 0.4572 0.3027 0.046 Uiso 1 1 calc R . . C19 C 0.5962(4) 0.5484(4) 0.34413(14) 0.0320(10) Uani 1 1 d U . . C20 C 0.5653(4) 0.4285(4) 0.36677(15) 0.0343(11) Uani 1 1 d U . . C21 C 0.7055(4) 0.5411(5) 0.07305(16) 0.0423(12) Uani 1 1 d U . . H21 H 0.6818 0.5254 0.0986 0.051 Uiso 1 1 calc R . . C22 C 0.6341(4) 0.5283(5) 0.03424(17) 0.0490(13) Uani 1 1 d U . . H22 H 0.5640 0.5049 0.0341 0.059 Uiso 1 1 calc R . . C23 C 0.6651(4) 0.5497(5) -0.00389(17) 0.0470(13) Uani 1 1 d U . . H23 H 0.6171 0.5409 -0.0302 0.056 Uiso 1 1 calc R . . C24 C 0.7716(4) 0.5854(5) -0.00263(15) 0.0409(12) Uani 1 1 d U . . C25 C 0.8134(5) 0.6108(5) -0.04084(17) 0.0534(13) Uani 1 1 d U . . H25 H 0.7693 0.6005 -0.0680 0.064 Uiso 1 1 calc R . . C26 C 0.9146(4) 0.6491(5) -0.03834(16) 0.0516(13) Uani 1 1 d U . . H26 H 0.9387 0.6680 -0.0636 0.062 Uiso 1 1 calc R . . C27 C 0.9859(4) 0.6609(5) 0.00308(17) 0.0470(12) Uani 1 1 d U . . C28 C 1.0921(4) 0.6990(6) 0.00725(19) 0.0587(14) Uani 1 1 d U . . H28 H 1.1193 0.7187 -0.0172 0.070 Uiso 1 1 calc R . . C29 C 1.1557(4) 0.7070(6) 0.0480(2) 0.0657(16) Uani 1 1 d U . . H29 H 1.2261 0.7344 0.0515 0.079 Uiso 1 1 calc R . . C30 C 1.1134(4) 0.6733(5) 0.08418(18) 0.0513(13) Uani 1 1 d U . . H30 H 1.1578 0.6766 0.1115 0.062 Uiso 1 1 calc R . . C31 C 0.9495(4) 0.6336(5) 0.04051(15) 0.0373(10) Uani 1 1 d U . . C32 C 0.8402(4) 0.5965(4) 0.03859(15) 0.0372(11) Uani 1 1 d U . . C33 C 0.7791(4) 0.0765(6) 0.41173(19) 0.0587(14) Uani 1 1 d U . . H33 H 0.7907 0.0755 0.3835 0.070 Uiso 1 1 calc R . . C34 C 0.8605(5) 0.0426(7) 0.4456(2) 0.0754(18) Uani 1 1 d U . . H34 H 0.9253 0.0153 0.4398 0.091 Uiso 1 1 calc R . . C35 C 0.8481(5) 0.0481(6) 0.4870(2) 0.0703(17) Uani 1 1 d U . . H35 H 0.9044 0.0260 0.5095 0.084 Uiso 1 1 calc R . . C36 C 0.7481(5) 0.0880(5) 0.49665(18) 0.0581(15) Uani 1 1 d U . . C37 C 0.7259(6) 0.0988(6) 0.53879(19) 0.0657(16) Uani 1 1 d U . . H37 H 0.7798 0.0839 0.5629 0.079 Uiso 1 1 calc R . . C38 C 0.6295(5) 0.1299(5) 0.54427(17) 0.0605(15) Uani 1 1 d U . . H38 H 0.6177 0.1355 0.5724 0.073 Uiso 1 1 calc R . . C39 C 0.5415(5) 0.1557(5) 0.50847(16) 0.0497(13) Uani 1 1 d U . . C40 C 0.4384(5) 0.1877(5) 0.5121(2) 0.0619(15) Uani 1 1 d U . . H40 H 0.4214 0.1937 0.5394 0.074 Uiso 1 1 calc R . . C41 C 0.3637(5) 0.2100(5) 0.4766(2) 0.0606(15) Uani 1 1 d U . . H41 H 0.2948 0.2305 0.4794 0.073 Uiso 1 1 calc R . . C42 C 0.3882(4) 0.2026(5) 0.43470(18) 0.0480(12) Uani 1 1 d U . . H42 H 0.3355 0.2205 0.4104 0.058 Uiso 1 1 calc R . . C43 C 0.5620(4) 0.1485(4) 0.46582(15) 0.0384(11) Uani 1 1 d U . . C44 C 0.6675(4) 0.1151(4) 0.46018(15) 0.0402(11) Uani 1 1 d U . . C45 C 0.5666(4) -0.0853(4) 0.34956(15) 0.0376(11) Uani 1 1 d U . . C46 C 0.5955(4) -0.2185(4) 0.33554(14) 0.0344(10) Uani 1 1 d U . . C47 C 0.6463(4) -0.2308(4) 0.30087(15) 0.0382(11) Uani 1 1 d U . . H47 H 0.6622 -0.1571 0.2864 0.046 Uiso 1 1 calc R . . C48 C 0.5705(3) -0.3277(4) 0.35664(14) 0.0347(10) Uani 1 1 d U . . H48 H 0.5358 -0.3187 0.3797 0.042 Uiso 1 1 calc R . . C49 C 0.3140(4) 0.0708(5) 0.32567(16) 0.0475(13) Uani 1 1 d U . . H49 H 0.3142 0.0242 0.3510 0.057 Uiso 1 1 calc R . . C50 C 0.3936(4) 0.2163(5) 0.28740(17) 0.0550(14) Uani 1 1 d U . . H50 H 0.4488 0.2735 0.2859 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0417(4) 0.0255(3) 0.0303(4) 0.0004(3) 0.0073(3) 0.0047(3) Co2 0.0405(3) 0.0228(3) 0.0272(3) -0.0012(2) 0.0075(3) -0.0050(3) N1 0.037(2) 0.044(2) 0.042(2) -0.0033(18) 0.0131(17) -0.0006(17) N2 0.038(2) 0.0272(19) 0.034(2) 0.0012(15) 0.0110(16) 0.0018(15) N3 0.039(2) 0.038(2) 0.044(2) -0.0026(17) 0.0097(18) -0.0064(17) N4 0.042(2) 0.0224(18) 0.041(2) 0.0004(15) 0.0157(17) -0.0035(15) N5 0.044(2) 0.029(2) 0.039(2) 0.0023(17) 0.0024(18) -0.0053(17) N6 0.050(2) 0.032(2) 0.037(2) 0.0067(17) 0.0149(17) 0.0059(18) O1 0.0520(19) 0.0214(17) 0.051(2) 0.0007(14) 0.0088(16) 0.0041(14) O2 0.079(3) 0.041(2) 0.064(3) 0.0088(18) -0.022(2) 0.0049(19) O3 0.055(2) 0.0266(18) 0.0470(19) 0.0003(14) 0.0005(16) -0.0006(15) O4 0.053(2) 0.0304(19) 0.055(2) -0.0014(15) -0.0040(17) -0.0045(15) O5 0.059(2) 0.0222(17) 0.0468(19) -0.0003(14) 0.0158(16) -0.0035(14) O6 0.059(2) 0.0292(18) 0.051(2) -0.0039(15) 0.0241(17) 0.0062(15) O7 0.0542(19) 0.0224(17) 0.0457(19) -0.0010(14) 0.0180(15) -0.0039(14) O8 0.099(3) 0.034(2) 0.064(3) 0.0115(18) 0.049(2) 0.0069(19) C1 0.045(3) 0.023(2) 0.037(3) 0.0043(19) 0.004(2) 0.006(2) C2 0.042(3) 0.020(2) 0.037(3) 0.0017(19) 0.007(2) 0.0025(19) C3 0.052(3) 0.021(2) 0.046(3) -0.004(2) 0.005(2) -0.005(2) C4 0.050(3) 0.025(2) 0.033(2) -0.0009(19) 0.000(2) -0.003(2) C5 0.040(2) 0.022(2) 0.042(3) -0.0007(19) 0.004(2) -0.0004(18) C6 0.036(2) 0.027(2) 0.030(2) 0.0017(18) -0.0004(19) 0.0006(18) C7 0.042(2) 0.026(2) 0.039(3) 0.0032(19) -0.001(2) 0.0026(19) C8 0.044(3) 0.027(2) 0.045(3) -0.002(2) -0.001(2) 0.001(2) C9 0.045(3) 0.026(2) 0.047(3) 0.002(2) 0.001(2) -0.003(2) C10 0.067(3) 0.047(3) 0.045(3) 0.017(2) -0.009(3) -0.017(3) C11 0.043(3) 0.050(3) 0.043(3) 0.001(2) 0.001(2) -0.014(2) C12 0.053(3) 0.046(3) 0.042(3) 0.008(2) 0.013(2) 0.014(2) C13 0.049(3) 0.043(3) 0.044(3) 0.001(2) 0.014(2) 0.015(2) C14 0.049(3) 0.025(2) 0.034(2) -0.0013(19) 0.019(2) -0.001(2) C15 0.070(3) 0.038(3) 0.043(3) 0.009(2) 0.026(2) 0.017(2) C16 0.058(3) 0.039(3) 0.047(3) 0.007(2) 0.019(2) 0.015(2) C17 0.052(3) 0.029(2) 0.038(3) -0.002(2) 0.021(2) 0.000(2) C18 0.052(3) 0.024(2) 0.042(3) -0.004(2) 0.017(2) 0.001(2) C19 0.046(3) 0.020(2) 0.031(2) 0.0014(18) 0.010(2) -0.0009(19) C20 0.041(3) 0.028(3) 0.034(3) 0.003(2) 0.007(2) -0.0026(19) C21 0.046(3) 0.039(3) 0.044(3) 0.001(2) 0.014(2) 0.001(2) C22 0.041(3) 0.047(3) 0.055(3) -0.003(2) -0.001(2) -0.003(2) C23 0.045(3) 0.044(3) 0.046(3) -0.001(2) -0.005(2) 0.004(2) C24 0.046(3) 0.038(3) 0.037(3) -0.003(2) 0.005(2) 0.004(2) C25 0.066(3) 0.052(3) 0.040(3) -0.001(2) 0.005(2) 0.009(3) C26 0.064(3) 0.053(3) 0.040(3) 0.003(2) 0.016(2) 0.004(3) C27 0.053(3) 0.042(3) 0.049(3) 0.002(2) 0.017(2) 0.001(2) C28 0.058(3) 0.064(3) 0.061(3) 0.005(3) 0.028(3) 0.000(3) C29 0.048(3) 0.076(4) 0.079(4) -0.001(3) 0.028(3) -0.014(3) C30 0.044(3) 0.056(3) 0.054(3) -0.006(2) 0.009(2) 0.001(2) C31 0.041(2) 0.038(2) 0.036(2) -0.002(2) 0.015(2) 0.000(2) C32 0.042(2) 0.032(2) 0.037(2) 0.0015(19) 0.007(2) 0.003(2) C33 0.045(3) 0.065(3) 0.066(3) -0.002(3) 0.011(3) 0.002(3) C34 0.057(3) 0.081(4) 0.083(4) 0.011(3) 0.002(3) 0.003(3) C35 0.060(3) 0.068(4) 0.070(4) 0.015(3) -0.020(3) 0.002(3) C36 0.067(3) 0.047(3) 0.052(3) 0.004(2) -0.008(3) -0.010(3) C37 0.090(4) 0.053(3) 0.042(3) 0.004(3) -0.013(3) -0.018(3) C38 0.104(4) 0.046(3) 0.031(3) -0.001(2) 0.014(3) -0.022(3) C39 0.080(3) 0.031(3) 0.043(3) -0.003(2) 0.024(3) -0.018(2) C40 0.093(4) 0.048(3) 0.057(3) -0.011(3) 0.043(3) -0.016(3) C41 0.074(4) 0.041(3) 0.082(4) -0.013(3) 0.050(3) -0.009(3) C42 0.056(3) 0.035(3) 0.057(3) -0.005(2) 0.020(2) -0.002(2) C43 0.057(3) 0.026(2) 0.036(2) -0.0035(19) 0.020(2) -0.011(2) C44 0.052(3) 0.032(2) 0.034(2) 0.0032(19) 0.002(2) -0.009(2) C45 0.051(3) 0.026(2) 0.035(3) -0.006(2) 0.007(2) 0.007(2) C46 0.047(3) 0.023(2) 0.036(3) 0.0008(19) 0.015(2) -0.0034(19) C47 0.051(3) 0.024(2) 0.044(3) -0.001(2) 0.021(2) 0.002(2) C48 0.046(3) 0.028(3) 0.033(2) 0.0000(19) 0.017(2) 0.0007(19) C49 0.056(3) 0.049(3) 0.039(3) 0.004(2) 0.013(2) -0.012(2) C50 0.064(3) 0.039(3) 0.054(3) 0.011(2) -0.006(3) -0.018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.017(3) . ? Co1 N2 2.079(4) . ? Co1 O3 2.123(3) . ? Co1 N6 2.144(4) . ? Co1 N1 2.150(4) . ? Co1 O4 2.289(4) . ? Co1 C4 2.514(5) . ? Co2 O7 2.018(3) . ? Co2 N4 2.091(4) . ? Co2 O5 2.114(3) . ? Co2 N5 2.131(4) . ? Co2 N3 2.140(4) . ? Co2 O6 2.322(4) . ? N1 C30 1.333(6) . ? N1 C31 1.370(6) . ? N2 C21 1.331(6) . ? N2 C32 1.345(6) . ? N3 C44 1.350(6) . ? N3 C33 1.351(7) . ? N4 C42 1.354(6) . ? N4 C43 1.353(6) . ? N5 C50 1.340(6) . ? N5 C49 1.347(6) . ? N6 C16 1.322(6) . ? N6 C12 1.344(6) . ? O1 C1 1.276(5) . ? O2 C1 1.236(5) . ? O3 C4 1.269(5) . ? O4 C4 1.231(5) . ? O5 C45 1.272(6) . ? O6 C45 1.243(6) . ? O7 C20 1.281(5) . ? O8 C20 1.231(5) . ? C1 C2 1.519(6) . ? C2 C3 1.374(6) . ? C2 C6 1.402(6) 1_545 ? C3 C8 1.399(6) 1_545 ? C4 C5 1.513(6) . ? C5 C7 1.369(6) . ? C5 C6 1.404(6) . ? C6 C2 1.402(6) 1_565 ? C7 C8 1.401(6) . ? C8 C3 1.399(6) 1_565 ? C8 C9 1.470(6) . ? C9 C10 1.382(7) . ? C9 C11 1.385(7) . ? C10 C50 1.386(7) 1_665 ? C11 C49 1.374(6) 1_665 ? C12 C13 1.376(6) . ? C13 C14 1.384(6) . ? C14 C15 1.394(6) . ? C14 C17 1.484(6) . ? C15 C16 1.393(6) . ? C17 C18 1.388(6) . ? C17 C47 1.405(6) 1_565 ? C18 C19 1.395(6) . ? C19 C48 1.396(6) 1_565 ? C19 C20 1.521(6) . ? C21 C22 1.376(6) . ? C22 C23 1.357(7) . ? C23 C24 1.408(7) . ? C24 C32 1.417(6) . ? C24 C25 1.438(7) . ? C25 C26 1.343(7) . ? C26 C27 1.437(7) . ? C27 C31 1.382(7) . ? C27 C28 1.399(7) . ? C28 C29 1.375(8) . ? C29 C30 1.403(7) . ? C31 C32 1.442(6) . ? C33 C34 1.378(7) . ? C34 C35 1.346(9) . ? C35 C36 1.436(9) . ? C36 C44 1.408(7) . ? C36 C37 1.417(8) . ? C37 C38 1.321(8) . ? C38 C39 1.448(8) . ? C39 C40 1.390(8) . ? C39 C43 1.422(7) . ? C40 C41 1.335(8) . ? C41 C42 1.420(7) . ? C43 C44 1.442(7) . ? C45 C46 1.513(6) . ? C46 C48 1.378(6) . ? C46 C47 1.386(6) . ? C47 C17 1.405(6) 1_545 ? C48 C19 1.396(6) 1_545 ? C49 C11 1.374(6) 1_445 ? C50 C10 1.386(7) 1_445 ? 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 Co1 N2 107.02(13) . . ? O1 Co1 O3 104.18(13) . . ? N2 Co1 O3 146.85(13) . . ? O1 Co1 N6 93.03(14) . . ? N2 Co1 N6 99.56(16) . . ? O3 Co1 N6 89.61(15) . . ? O1 Co1 N1 96.36(15) . . ? N2 Co1 N1 78.80(15) . . ? O3 Co1 N1 86.97(14) . . ? N6 Co1 N1 170.54(15) . . ? O1 Co1 O4 163.68(12) . . ? N2 Co1 O4 89.05(12) . . ? O3 Co1 O4 59.50(12) . . ? N6 Co1 O4 86.87(14) . . ? N1 Co1 O4 83.79(14) . . ? O1 Co1 C4 134.48(14) . . ? N2 Co1 C4 117.50(14) . . ? O3 Co1 C4 30.30(12) . . ? N6 Co1 C4 88.75(16) . . ? N1 Co1 C4 83.85(16) . . ? O4 Co1 C4 29.22(12) . . ? O7 Co2 N4 109.98(14) . . ? O7 Co2 O5 103.14(13) . . ? N4 Co2 O5 144.27(13) . . ? O7 Co2 N5 93.37(14) . . ? N4 Co2 N5 101.69(15) . . ? O5 Co2 N5 89.11(14) . . ? O7 Co2 N3 94.74(14) . . ? N4 Co2 N3 78.11(16) . . ? O5 Co2 N3 86.34(14) . . ? N5 Co2 N3 171.42(15) . . ? O7 Co2 O6 162.32(13) . . ? N4 Co2 O6 87.10(13) . . ? O5 Co2 O6 59.19(12) . . ? N5 Co2 O6 87.31(13) . . ? N3 Co2 O6 84.12(13) . . ? C30 N1 C31 116.8(4) . . ? C30 N1 Co1 130.2(3) . . ? C31 N1 Co1 112.6(3) . . ? C21 N2 C32 117.8(4) . . ? C21 N2 Co1 128.3(3) . . ? C32 N2 Co1 113.9(3) . . ? C44 N3 C33 119.2(4) . . ? C44 N3 Co2 113.4(3) . . ? C33 N3 Co2 127.2(4) . . ? C42 N4 C43 117.3(4) . . ? C42 N4 Co2 128.1(3) . . ? C43 N4 Co2 114.6(3) . . ? C50 N5 C49 116.9(4) . . ? C50 N5 Co2 118.3(3) . . ? C49 N5 Co2 122.6(3) . . ? C16 N6 C12 116.6(4) . . ? C16 N6 Co1 119.7(3) . . ? C12 N6 Co1 122.4(3) . . ? C1 O1 Co1 127.2(3) . . ? C4 O3 Co1 92.1(3) . . ? C4 O4 Co1 85.5(3) . . ? C45 O5 Co2 93.8(3) . . ? C45 O6 Co2 85.0(3) . . ? C20 O7 Co2 123.3(3) . . ? O2 C1 O1 125.4(4) . . ? O2 C1 C2 118.6(4) . . ? O1 C1 C2 116.1(4) . . ? C3 C2 C6 118.3(4) . 1_545 ? C3 C2 C1 121.9(4) . . ? C6 C2 C1 119.8(4) 1_545 . ? C2 C3 C8 122.7(4) . 1_545 ? O4 C4 O3 122.7(4) . . ? O4 C4 C5 119.5(4) . . ? O3 C4 C5 117.7(4) . . ? O4 C4 Co1 65.2(2) . . ? O3 C4 Co1 57.6(2) . . ? C5 C4 Co1 174.8(3) . . ? C7 C5 C6 120.2(4) . . ? C7 C5 C4 120.3(4) . . ? C6 C5 C4 119.4(4) . . ? C5 C6 C2 120.0(4) . 1_565 ? C5 C7 C8 120.9(4) . . ? C7 C8 C3 117.8(4) . 1_565 ? C7 C8 C9 121.3(4) . . ? C3 C8 C9 120.9(4) 1_565 . ? C10 C9 C11 117.0(4) . . ? C10 C9 C8 121.8(5) . . ? C11 C9 C8 121.3(4) . . ? C9 C10 C50 120.0(5) . 1_665 ? C49 C11 C9 120.2(5) 1_665 . ? N6 C12 C13 123.8(4) . . ? C12 C13 C14 119.4(4) . . ? C13 C14 C15 117.2(5) . . ? C13 C14 C17 121.5(4) . . ? C15 C14 C17 121.2(4) . . ? C14 C15 C16 118.9(4) . . ? N6 C16 C15 123.8(5) . . ? C18 C17 C47 118.3(4) . 1_565 ? C18 C17 C14 120.3(4) . . ? C47 C17 C14 121.3(4) 1_565 . ? C17 C18 C19 122.0(4) . . ? C18 C19 C48 117.8(4) . 1_565 ? C18 C19 C20 121.2(4) . . ? C48 C19 C20 120.9(4) 1_565 . ? O8 C20 O7 125.5(4) . . ? O8 C20 C19 118.2(4) . . ? O7 C20 C19 116.2(4) . . ? N2 C21 C22 123.2(5) . . ? C23 C22 C21 120.5(5) . . ? C22 C23 C24 118.4(4) . . ? C23 C24 C32 117.7(5) . . ? C23 C24 C25 123.3(4) . . ? C32 C24 C25 118.9(5) . . ? C26 C25 C24 121.7(5) . . ? C25 C26 C27 120.4(5) . . ? C31 C27 C28 118.0(5) . . ? C31 C27 C26 119.6(5) . . ? C28 C27 C26 122.4(5) . . ? C29 C28 C27 119.1(5) . . ? C28 C29 C30 119.3(5) . . ? N1 C30 C29 123.0(5) . . ? N1 C31 C27 123.8(4) . . ? N1 C31 C32 115.4(4) . . ? C27 C31 C32 120.8(4) . . ? N2 C32 C24 122.4(4) . . ? N2 C32 C31 119.1(4) . . ? C24 C32 C31 118.5(5) . . ? N3 C33 C34 120.7(6) . . ? C35 C34 C33 121.3(6) . . ? C34 C35 C36 120.2(5) . . ? C44 C36 C37 119.6(6) . . ? C44 C36 C35 115.1(6) . . ? C37 C36 C35 125.3(5) . . ? C38 C37 C36 120.9(5) . . ? C37 C38 C39 123.0(6) . . ? C40 C39 C43 116.8(5) . . ? C40 C39 C38 125.7(5) . . ? C43 C39 C38 117.5(5) . . ? C41 C40 C39 120.3(6) . . ? C40 C41 C42 120.8(6) . . ? N4 C42 C41 121.1(5) . . ? N4 C43 C39 123.7(5) . . ? N4 C43 C44 117.2(4) . . ? C39 C43 C44 119.2(4) . . ? N3 C44 C36 123.4(5) . . ? N3 C44 C43 116.7(4) . . ? C36 C44 C43 119.9(5) . . ? O6 C45 O5 121.9(4) . . ? O6 C45 C46 120.3(4) . . ? O5 C45 C46 117.8(4) . . ? C48 C46 C47 119.9(4) . . ? C48 C46 C45 120.5(4) . . ? C47 C46 C45 119.7(4) . . ? C46 C47 C17 120.5(4) . 1_545 ? C46 C48 C19 121.4(4) . 1_545 ? N5 C49 C11 123.0(5) . 1_445 ? N5 C50 C10 122.9(5) . 1_445 ? _diffrn_measured_fraction_theta_max 0.890 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.890 _refine_diff_density_max 1.357 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 937601' ####################################################################### # # 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 ? _chemical_formula_sum 'C30 H40 N6 Ni2 O13' _chemical_formula_weight 810.10 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' Ni Ni 0.3393 1.1124 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.254(4) _cell_length_b 13.361(6) _cell_length_c 16.140(5) _cell_angle_alpha 90.00 _cell_angle_beta 125.468(18) _cell_angle_gamma 90.00 _cell_volume 1800.9(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 1.116 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7994 _exptl_absorpt_correction_T_max 0.8076 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9970 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3160 _reflns_number_gt 2735 _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^)+(0.0522P)^2^+2.6097P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3160 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.51544(4) 0.18751(3) 0.52517(3) 0.02323(14) Uani 1 1 d . . . O1 O 0.3203(3) 0.20236(16) 0.54122(17) 0.0308(5) Uani 1 1 d . . . O2 O 0.2856(3) 0.11747(16) 0.41323(17) 0.0314(5) Uani 1 1 d . . . O3 O -0.1464(4) 0.2424(3) 0.5619(3) 0.0876(13) Uani 1 1 d . . . O4 O -0.3500(2) 0.13665(16) 0.47719(16) 0.0290(5) Uani 1 1 d . . . O5 O 0.1165(6) 0.3642(3) 0.6923(3) 0.1106(15) Uani 1 1 d . . . H5C H 0.1548 0.3629 0.7552 0.133 Uiso 1 1 d R . . H5D H 0.0374 0.3243 0.6608 0.133 Uiso 1 1 d R . . O6 O 0.1599(15) 0.5388(7) 0.5193(7) 0.142(5) Uani 0.50 1 d P . . H6C H 0.2432 0.5068 0.5645 0.170 Uiso 0.50 1 d PR . . H6D H 0.1876 0.5958 0.5111 0.170 Uiso 0.50 1 d PR . . O7 O 0.3747(6) 0.3829(3) 0.6599(3) 0.1139(16) Uani 1 1 d . . . H7C H 0.3639 0.3316 0.6252 0.137 Uiso 1 1 d R . . H7D H 0.3036 0.3807 0.6713 0.137 Uiso 1 1 d R . . N1 N -0.4300(3) -0.19068(19) 0.0757(2) 0.0315(6) Uani 1 1 d . . . N2 N 0.6853(4) 0.2634(2) 0.6550(2) 0.0406(7) Uani 1 1 d . . . H2A H 0.7530 0.2954 0.6456 0.049 Uiso 1 1 calc R . . H2B H 0.6381 0.3091 0.6705 0.049 Uiso 1 1 calc R . . N3 N 0.5940(3) 0.0655(2) 0.6232(2) 0.0334(6) Uani 1 1 d . . . H3A H 0.5104 0.0356 0.6174 0.040 Uiso 1 1 calc R . . H3B H 0.6418 0.0205 0.6075 0.040 Uiso 1 1 calc R . . C1 C 0.7726(9) 0.1910(4) 0.7372(4) 0.117(3) Uani 1 1 d . . . H1A H 0.8759 0.1802 0.7494 0.140 Uiso 1 1 calc R . . H1B H 0.7926 0.2213 0.7982 0.140 Uiso 1 1 calc R . . C2 C 0.7062(8) 0.1014(4) 0.7259(3) 0.099(2) Uani 1 1 d . . . H2C H 0.6516 0.1035 0.7587 0.118 Uiso 1 1 calc R . . H2D H 0.7918 0.0527 0.7621 0.118 Uiso 1 1 calc R . . C3 C 0.2339(4) 0.1490(2) 0.4636(2) 0.0273(7) Uani 1 1 d . . . C4 C 0.0669(4) 0.1210(2) 0.4285(2) 0.0267(7) Uani 1 1 d . . . C5 C 0.0039(4) 0.1581(2) 0.4790(2) 0.0270(7) Uani 1 1 d . . . H5 H 0.0638 0.2018 0.5335 0.032 Uiso 1 1 calc R . . C6 C -0.1492(4) 0.1296(2) 0.4476(2) 0.0270(7) Uani 1 1 d . . . C7 C -0.2364(4) 0.0632(2) 0.3674(2) 0.0278(7) Uani 1 1 d . . . H7 H -0.3377 0.0434 0.3475 0.033 Uiso 1 1 calc R . . C8 C -0.1746(4) 0.0254(2) 0.3160(2) 0.0278(7) Uani 1 1 d . . . C9 C -0.0223(4) 0.0556(2) 0.3473(2) 0.0281(7) Uani 1 1 d . . . H9 H 0.0200 0.0316 0.3135 0.034 Uiso 1 1 calc R . . C10 C -0.2192(4) 0.1730(3) 0.5010(3) 0.0346(8) Uani 1 1 d . . . C11 C -0.2663(4) -0.0471(2) 0.2315(2) 0.0295(7) Uani 1 1 d . . . C12 C -0.3488(4) -0.1260(3) 0.2376(3) 0.0371(8) Uani 1 1 d . . . H12 H -0.3513 -0.1322 0.2941 0.044 Uiso 1 1 calc R . . C13 C -0.4267(4) -0.1947(3) 0.1604(3) 0.0377(8) Uani 1 1 d . . . H13 H -0.4802 -0.2470 0.1667 0.045 Uiso 1 1 calc R . . C14 C -0.3525(5) -0.1142(3) 0.0692(3) 0.0398(8) Uani 1 1 d . . . H14 H -0.3546 -0.1087 0.0110 0.048 Uiso 1 1 calc R . . C15 C -0.2694(5) -0.0428(3) 0.1444(3) 0.0398(8) Uani 1 1 d . . . H15 H -0.2155 0.0082 0.1366 0.048 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 Ni1 0.0222(2) 0.0257(2) 0.0281(2) -0.00204(16) 0.01822(18) -0.00103(15) O1 0.0257(12) 0.0380(12) 0.0358(12) -0.0056(10) 0.0219(11) -0.0031(9) O2 0.0269(12) 0.0382(12) 0.0396(13) -0.0051(10) 0.0254(11) -0.0016(9) O3 0.064(2) 0.128(3) 0.110(3) -0.086(3) 0.073(2) -0.059(2) O4 0.0249(12) 0.0349(12) 0.0363(12) -0.0034(10) 0.0230(10) -0.0026(9) O5 0.136(4) 0.114(3) 0.082(3) -0.024(3) 0.064(3) -0.048(3) O6 0.259(13) 0.087(6) 0.102(6) 0.045(5) 0.118(8) 0.074(8) O7 0.169(5) 0.105(3) 0.097(3) -0.009(3) 0.094(3) 0.001(3) N1 0.0342(15) 0.0322(14) 0.0360(15) -0.0033(12) 0.0249(13) -0.0023(12) N2 0.0471(19) 0.0394(16) 0.0432(17) -0.0146(14) 0.0307(16) -0.0131(14) N3 0.0386(16) 0.0295(14) 0.0423(16) 0.0012(12) 0.0293(14) 0.0030(12) C1 0.127(6) 0.089(4) 0.036(3) 0.008(3) -0.008(3) -0.052(4) C2 0.136(5) 0.055(3) 0.036(3) 0.004(2) 0.011(3) 0.006(3) C3 0.0250(16) 0.0291(15) 0.0362(18) 0.0043(14) 0.0225(15) 0.0034(13) C4 0.0231(16) 0.0297(16) 0.0327(16) 0.0044(13) 0.0194(14) 0.0024(12) C5 0.0230(15) 0.0341(17) 0.0292(16) -0.0019(13) 0.0182(14) -0.0005(13) C6 0.0234(16) 0.0347(17) 0.0296(16) 0.0017(13) 0.0192(14) 0.0002(13) C7 0.0229(15) 0.0322(16) 0.0349(17) 0.0030(13) 0.0205(14) -0.0002(13) C8 0.0286(17) 0.0278(15) 0.0327(17) 0.0023(13) 0.0210(14) 0.0004(13) C9 0.0284(16) 0.0309(16) 0.0341(17) 0.0000(13) 0.0233(15) 0.0021(13) C10 0.0289(18) 0.0448(19) 0.0389(19) -0.0104(15) 0.0248(16) -0.0053(15) C11 0.0281(16) 0.0303(16) 0.0352(17) -0.0015(13) 0.0213(15) -0.0007(13) C12 0.041(2) 0.046(2) 0.0362(18) -0.0057(16) 0.0295(17) -0.0108(16) C13 0.040(2) 0.0429(19) 0.0405(19) -0.0063(16) 0.0294(17) -0.0133(16) C14 0.060(2) 0.0351(18) 0.0408(19) -0.0044(15) 0.0391(19) -0.0081(17) C15 0.059(2) 0.0321(17) 0.046(2) -0.0053(15) 0.0406(19) -0.0123(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 Ni1 O4 2.051(2) 1_655 ? Ni1 N2 2.054(3) . ? Ni1 N3 2.081(3) . ? Ni1 N1 2.101(3) 2 ? Ni1 O1 2.170(2) . ? Ni1 O2 2.180(2) . ? Ni1 C3 2.501(3) . ? O1 C3 1.255(4) . ? O2 C3 1.273(4) . ? O3 C10 1.238(4) . ? O4 C10 1.259(4) . ? O4 Ni1 2.051(2) 1_455 ? O5 H5C 0.8500 . ? O5 H5D 0.8499 . ? O6 H6C 0.8500 . ? O6 H6D 0.8500 . ? O7 H7C 0.8500 . ? O7 H7D 0.8501 . ? N1 C14 1.336(4) . ? N1 C13 1.348(4) . ? N1 Ni1 2.101(3) 2_545 ? N2 C1 1.455(6) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N3 C2 1.445(5) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? C1 C2 1.336(7) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2C 0.9700 . ? C2 H2D 0.9700 . ? C3 C4 1.506(4) . ? C4 C9 1.387(4) . ? C4 C5 1.392(4) . ? C5 C6 1.394(4) . ? C5 H5 0.9300 . ? C6 C7 1.386(4) . ? C6 C10 1.520(4) . ? C7 C8 1.398(4) . ? C7 H7 0.9300 . ? C8 C9 1.393(4) . ? C8 C11 1.481(4) . ? C9 H9 0.9300 . ? C11 C15 1.390(4) . ? C11 C12 1.391(4) . ? C12 C13 1.371(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.381(5) . ? C14 H14 0.9300 . ? C15 H15 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 O4 Ni1 N2 100.99(11) 1_655 . ? O4 Ni1 N3 88.79(10) 1_655 . ? N2 Ni1 N3 83.45(12) . . ? O4 Ni1 N1 91.91(9) 1_655 2 ? N2 Ni1 N1 97.70(12) . 2 ? N3 Ni1 N1 178.51(11) . 2 ? O4 Ni1 O1 160.77(9) 1_655 . ? N2 Ni1 O1 97.35(11) . . ? N3 Ni1 O1 87.59(10) . . ? N1 Ni1 O1 91.32(9) 2 . ? O4 Ni1 O2 100.69(9) 1_655 . ? N2 Ni1 O2 157.90(10) . . ? N3 Ni1 O2 92.82(10) . . ? N1 Ni1 O2 85.76(10) 2 . ? O1 Ni1 O2 60.66(8) . . ? O4 Ni1 C3 131.01(10) 1_655 . ? N2 Ni1 C3 127.37(11) . . ? N3 Ni1 C3 89.39(11) . . ? N1 Ni1 C3 89.16(10) 2 . ? O1 Ni1 C3 30.10(9) . . ? O2 Ni1 C3 30.58(9) . . ? C3 O1 Ni1 89.70(17) . . ? C3 O2 Ni1 88.79(19) . . ? C10 O4 Ni1 126.0(2) . 1_455 ? H5C O5 H5D 108.7 . . ? H6C O6 H6D 108.9 . . ? H7C O7 H7D 108.3 . . ? C14 N1 C13 116.4(3) . . ? C14 N1 Ni1 122.1(2) . 2_545 ? C13 N1 Ni1 120.6(2) . 2_545 ? C1 N2 Ni1 108.2(3) . . ? C1 N2 H2A 110.1 . . ? Ni1 N2 H2A 110.1 . . ? C1 N2 H2B 110.1 . . ? Ni1 N2 H2B 110.1 . . ? H2A N2 H2B 108.4 . . ? C2 N3 Ni1 108.1(3) . . ? C2 N3 H3A 110.1 . . ? Ni1 N3 H3A 110.1 . . ? C2 N3 H3B 110.1 . . ? Ni1 N3 H3B 110.1 . . ? H3A N3 H3B 108.4 . . ? C2 C1 N2 118.4(4) . . ? C2 C1 H1A 107.7 . . ? N2 C1 H1A 107.7 . . ? C2 C1 H1B 107.7 . . ? N2 C1 H1B 107.7 . . ? H1A C1 H1B 107.1 . . ? C1 C2 N3 117.3(4) . . ? C1 C2 H2C 108.0 . . ? N3 C2 H2C 108.0 . . ? C1 C2 H2D 108.0 . . ? N3 C2 H2D 108.0 . . ? H2C C2 H2D 107.2 . . ? O1 C3 O2 120.8(3) . . ? O1 C3 C4 120.5(3) . . ? O2 C3 C4 118.8(3) . . ? O1 C3 Ni1 60.19(15) . . ? O2 C3 Ni1 60.63(16) . . ? C4 C3 Ni1 177.3(2) . . ? C9 C4 C5 120.1(3) . . ? C9 C4 C3 119.7(3) . . ? C5 C4 C3 120.2(3) . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 119.7(3) . . ? C7 C6 C10 120.8(3) . . ? C5 C6 C10 119.5(3) . . ? C6 C7 C8 121.1(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 118.6(3) . . ? C9 C8 C11 120.1(3) . . ? C7 C8 C11 121.3(3) . . ? C4 C9 C8 120.8(3) . . ? C4 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? O3 C10 O4 125.2(3) . . ? O3 C10 C6 118.0(3) . . ? O4 C10 C6 116.8(3) . . ? C15 C11 C12 116.5(3) . . ? C15 C11 C8 122.3(3) . . ? C12 C11 C8 121.2(3) . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? N1 C13 C12 123.7(3) . . ? N1 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? N1 C14 C15 123.5(3) . . ? N1 C14 H14 118.3 . . ? C15 C14 H14 118.3 . . ? C14 C15 C11 120.0(3) . . ? C14 C15 H15 120.0 . . ? C11 C15 H15 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Ni1 O1 C3 -13.6(4) 1_655 . . . ? N2 Ni1 O1 C3 -176.01(19) . . . . ? N3 Ni1 O1 C3 -92.94(19) . . . . ? N1 Ni1 O1 C3 86.05(19) 2 . . . ? O2 Ni1 O1 C3 1.66(17) . . . . ? O4 Ni1 O2 C3 173.31(17) 1_655 . . . ? N2 Ni1 O2 C3 4.5(4) . . . . ? N3 Ni1 O2 C3 84.01(19) . . . . ? N1 Ni1 O2 C3 -95.54(18) 2 . . . ? O1 Ni1 O2 C3 -1.63(17) . . . . ? O4 Ni1 N2 C1 -82.1(4) 1_655 . . . ? N3 Ni1 N2 C1 5.4(4) . . . . ? N1 Ni1 N2 C1 -175.6(4) 2 . . . ? O1 Ni1 N2 C1 92.1(4) . . . . ? O2 Ni1 N2 C1 86.6(5) . . . . ? C3 Ni1 N2 C1 89.5(4) . . . . ? O4 Ni1 N3 C2 107.6(4) 1_655 . . . ? N2 Ni1 N3 C2 6.4(4) . . . . ? N1 Ni1 N3 C2 -134(4) 2 . . . ? O1 Ni1 N3 C2 -91.3(4) . . . . ? O2 Ni1 N3 C2 -151.8(4) . . . . ? C3 Ni1 N3 C2 -121.4(4) . . . . ? Ni1 N2 C1 C2 -18.4(9) . . . . ? N2 C1 C2 N3 26.1(11) . . . . ? Ni1 N3 C2 C1 -19.0(8) . . . . ? Ni1 O1 C3 O2 -2.9(3) . . . . ? Ni1 O1 C3 C4 177.0(3) . . . . ? Ni1 O2 C3 O1 2.9(3) . . . . ? Ni1 O2 C3 C4 -177.0(2) . . . . ? O4 Ni1 C3 O1 174.12(16) 1_655 . . . ? N2 Ni1 C3 O1 5.0(2) . . . . ? N3 Ni1 C3 O1 86.25(19) . . . . ? N1 Ni1 C3 O1 -94.08(19) 2 . . . ? O2 Ni1 C3 O1 -177.2(3) . . . . ? O4 Ni1 C3 O2 -8.7(2) 1_655 . . . ? N2 Ni1 C3 O2 -177.86(17) . . . . ? N3 Ni1 C3 O2 -96.59(18) . . . . ? N1 Ni1 C3 O2 83.08(18) 2 . . . ? O1 Ni1 C3 O2 177.2(3) . . . . ? O4 Ni1 C3 C4 69(5) 1_655 . . . ? N2 Ni1 C3 C4 -101(5) . . . . ? N3 Ni1 C3 C4 -19(5) . . . . ? N1 Ni1 C3 C4 160(5) 2 . . . ? O1 Ni1 C3 C4 -105(5) . . . . ? O2 Ni1 C3 C4 77(5) . . . . ? O1 C3 C4 C9 -175.0(3) . . . . ? O2 C3 C4 C9 4.9(4) . . . . ? Ni1 C3 C4 C9 -71(5) . . . . ? O1 C3 C4 C5 3.2(5) . . . . ? O2 C3 C4 C5 -176.9(3) . . . . ? Ni1 C3 C4 C5 107(5) . . . . ? C9 C4 C5 C6 -0.2(5) . . . . ? C3 C4 C5 C6 -178.3(3) . . . . ? C4 C5 C6 C7 1.1(5) . . . . ? C4 C5 C6 C10 -178.1(3) . . . . ? C5 C6 C7 C8 -1.1(5) . . . . ? C10 C6 C7 C8 178.0(3) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? C6 C7 C8 C11 178.8(3) . . . . ? C5 C4 C9 C8 -0.7(5) . . . . ? C3 C4 C9 C8 177.4(3) . . . . ? C7 C8 C9 C4 0.7(5) . . . . ? C11 C8 C9 C4 -177.9(3) . . . . ? Ni1 O4 C10 O3 4.2(6) 1_455 . . . ? Ni1 O4 C10 C6 -173.9(2) 1_455 . . . ? C7 C6 C10 O3 -169.8(4) . . . . ? C5 C6 C10 O3 9.3(5) . . . . ? C7 C6 C10 O4 8.4(5) . . . . ? C5 C6 C10 O4 -172.5(3) . . . . ? C9 C8 C11 C15 -41.1(5) . . . . ? C7 C8 C11 C15 140.3(3) . . . . ? C9 C8 C11 C12 136.2(3) . . . . ? C7 C8 C11 C12 -42.3(5) . . . . ? C15 C11 C12 C13 0.5(5) . . . . ? C8 C11 C12 C13 -177.0(3) . . . . ? C14 N1 C13 C12 -0.3(5) . . . . ? Ni1 N1 C13 C12 168.7(3) 2_545 . . . ? C11 C12 C13 N1 -0.5(6) . . . . ? C13 N1 C14 C15 1.3(5) . . . . ? Ni1 N1 C14 C15 -167.5(3) 2_545 . . . ? N1 C14 C15 C11 -1.4(6) . . . . ? C12 C11 C15 C14 0.4(5) . . . . ? C8 C11 C15 C14 177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.717 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 937602' ####################################################################### # # 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 ? _chemical_formula_sum 'C26 H0 N0 O0 Pb' _chemical_formula_weight 519.45 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' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.318(10) _cell_length_b 10.274(16) _cell_length_c 10.462(11) _cell_angle_alpha 110.180(10) _cell_angle_beta 102.095(11) _cell_angle_gamma 98.619(13) _cell_volume 796.2(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 10.601 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4465 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2764 _reflns_number_gt 2528 _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^)+(0.0188P)^2^+16.5407P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2764 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pb1 Pb 1.37978(5) 0.31576(4) 0.56213(4) 0.02648(15) Uani 1 1 d . . . N1 N 1.0751(13) 0.1923(11) 0.3684(10) 0.041(3) Uani 1 1 d . . . N2 N 1.2016(12) 0.3572(11) 0.7283(10) 0.039(3) Uani 1 1 d . . . O1 O 0.3348(11) 0.0645(9) -0.4213(9) 0.045(2) Uani 1 1 d . . . O2 O 0.5401(10) 0.2476(8) -0.2611(9) 0.039(2) Uani 1 1 d . . . O3 O 0.3285(12) -0.4250(9) -0.4172(9) 0.046(2) Uani 1 1 d . . . O4 O 0.5230(12) -0.4453(9) -0.2504(9) 0.047(2) Uani 1 1 d . . . C1 C 1.0367(17) 0.3544(17) 0.6997(13) 0.054(4) Uani 1 1 d . . . H1 H 0.9731 0.3111 0.6050 0.065 Uiso 1 1 calc R . . C2 C 0.9520(16) 0.4107(18) 0.7991(14) 0.059(4) Uani 1 1 d . . . H2 H 0.8381 0.4097 0.7698 0.071 Uiso 1 1 calc R . . C3 C 1.0385(15) 0.4685(12) 0.9430(11) 0.031(3) Uani 1 1 d . . . C4 C 1.2069(14) 0.4598(12) 0.9716(11) 0.028(2) Uani 1 1 d . . . H4 H 1.2707 0.4926 1.0658 0.034 Uiso 1 1 calc R . . C5 C 1.2838(17) 0.4044(14) 0.8658(13) 0.043(3) Uani 1 1 d . . . H5 H 1.3963 0.4001 0.8917 0.052 Uiso 1 1 calc R . . C6 C 1.019(2) 0.2697(16) 0.2996(16) 0.072(5) Uani 1 1 d . . . H6 H 1.0604 0.3684 0.3420 0.086 Uiso 1 1 calc R . . C7 C 0.902(2) 0.2113(15) 0.1678(15) 0.062(5) Uani 1 1 d . . . H7 H 0.8647 0.2710 0.1248 0.074 Uiso 1 1 calc R . . C8 C 0.8406(14) 0.0649(12) 0.0988(12) 0.030(2) Uani 1 1 d . . . C9 C 0.8997(19) -0.0140(15) 0.1708(16) 0.059(4) Uani 1 1 d . . . H9 H 0.8606 -0.1130 0.1316 0.071 Uiso 1 1 calc R . . C10 C 1.019(2) 0.0537(15) 0.3038(14) 0.055(4) Uani 1 1 d . . . H10 H 1.0616 -0.0030 0.3487 0.066 Uiso 1 1 calc R . . C11 C 0.7103(14) -0.0011(11) -0.0431(11) 0.026(2) Uani 1 1 d . . . C12 C 0.6492(14) 0.0827(12) -0.1130(12) 0.031(3) Uani 1 1 d . . . H12 H 0.6935 0.1811 -0.0723 0.038 Uiso 1 1 calc R . . C13 C 0.5238(14) 0.0229(12) -0.2420(12) 0.031(3) Uani 1 1 d . . . C14 C 0.4543(14) -0.1245(12) -0.3016(11) 0.029(2) Uani 1 1 d . . . H14 H 0.3662 -0.1650 -0.3853 0.035 Uiso 1 1 calc R . . C15 C 0.5162(14) -0.2104(11) -0.2363(11) 0.027(2) Uani 1 1 d . . . C16 C 0.6419(14) -0.1478(12) -0.1068(11) 0.030(2) Uani 1 1 d . . . H16 H 0.6808 -0.2057 -0.0620 0.035 Uiso 1 1 calc R . . C17 C 0.4610(15) 0.1173(12) -0.3134(12) 0.032(3) Uani 1 1 d . . . C18 C 0.4485(16) -0.3722(12) -0.3057(12) 0.033(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.0301(2) 0.0231(2) 0.0231(2) 0.00815(16) 0.00361(16) 0.00516(16) N1 0.039(6) 0.042(6) 0.028(5) 0.007(5) -0.003(5) 0.007(5) N2 0.026(5) 0.034(6) 0.035(5) -0.004(4) -0.006(4) 0.009(4) O1 0.042(5) 0.034(5) 0.049(5) 0.021(4) -0.009(4) 0.003(4) O2 0.039(5) 0.022(4) 0.043(5) 0.009(4) -0.007(4) 0.006(3) O3 0.053(6) 0.028(5) 0.042(5) 0.011(4) -0.009(4) 0.006(4) O4 0.068(6) 0.025(5) 0.034(5) 0.010(4) -0.006(4) 0.007(4) C1 0.041(8) 0.084(11) 0.018(6) -0.001(6) 0.005(5) 0.017(7) C2 0.019(6) 0.099(13) 0.035(7) 0.000(8) 0.006(5) 0.008(7) C3 0.046(7) 0.026(6) 0.016(5) 0.005(4) 0.010(5) -0.003(5) C4 0.028(6) 0.039(7) 0.023(5) 0.015(5) 0.008(5) 0.012(5) C5 0.041(7) 0.044(8) 0.034(7) 0.009(6) -0.003(6) 0.013(6) C6 0.090(13) 0.034(8) 0.052(9) 0.005(7) -0.032(9) 0.001(8) C7 0.080(11) 0.035(8) 0.046(8) 0.013(6) -0.027(8) 0.013(7) C8 0.028(6) 0.029(6) 0.032(6) 0.014(5) 0.006(5) 0.005(5) C9 0.056(9) 0.036(8) 0.061(9) 0.020(7) -0.026(7) -0.002(6) C10 0.069(10) 0.041(8) 0.037(7) 0.016(6) -0.015(7) 0.003(7) C11 0.028(6) 0.026(6) 0.024(5) 0.010(5) 0.007(4) 0.005(4) C12 0.033(6) 0.024(6) 0.035(6) 0.008(5) 0.007(5) 0.009(5) C13 0.031(6) 0.022(6) 0.035(6) 0.009(5) 0.005(5) 0.009(5) C14 0.030(6) 0.026(6) 0.025(5) 0.006(5) 0.000(5) 0.007(5) C15 0.033(6) 0.022(6) 0.022(5) 0.005(4) 0.007(5) 0.004(5) C16 0.036(6) 0.029(6) 0.026(6) 0.015(5) 0.006(5) 0.007(5) C17 0.043(7) 0.026(6) 0.027(6) 0.011(5) 0.006(5) 0.010(5) C18 0.047(7) 0.019(6) 0.028(6) 0.007(5) 0.008(5) 0.002(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 Pb1 O2 2.414(8) 1_656 ? Pb1 O4 2.473(9) 1_666 ? Pb1 N2 2.481(11) . ? Pb1 O1 2.623(9) 1_656 ? Pb1 N1 2.693(10) . ? Pb1 O3 2.703(9) 1_666 ? Pb1 C17 2.860(11) 1_656 ? N1 C10 1.306(17) . ? N1 C6 1.316(18) . ? N2 C5 1.334(15) . ? N2 C1 1.335(16) . ? O1 C17 1.257(14) . ? O1 Pb1 2.623(9) 1_454 ? O2 C17 1.266(14) . ? O2 Pb1 2.414(8) 1_454 ? O3 C18 1.250(14) . ? O3 Pb1 2.703(9) 1_444 ? O4 C18 1.254(14) . ? O4 Pb1 2.473(8) 1_444 ? C1 C2 1.388(18) . ? C1 H1 0.9300 . ? C2 C3 1.392(16) . ? C2 H2 0.9300 . ? C3 C4 1.392(16) . ? C3 C3 1.47(2) 2_767 ? C4 C5 1.389(17) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.378(18) . ? C6 H6 0.9300 . ? C7 C8 1.383(17) . ? C7 H7 0.9300 . ? C8 C9 1.361(17) . ? C8 C11 1.500(15) . ? C9 C10 1.398(18) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.389(15) . ? C11 C12 1.395(15) . ? C12 C13 1.390(16) . ? C12 H12 0.9300 . ? C13 C14 1.397(15) . ? C13 C17 1.503(15) . ? C14 C15 1.385(15) . ? C14 H14 0.9300 . ? C15 C16 1.394(15) . ? C15 C18 1.524(15) . ? C16 H16 0.9300 . ? C17 Pb1 2.860(11) 1_454 ? 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 O2 Pb1 O4 80.1(3) 1_656 1_666 ? O2 Pb1 N2 81.0(3) 1_656 . ? O4 Pb1 N2 75.1(3) 1_666 . ? O2 Pb1 O1 52.1(3) 1_656 1_656 ? O4 Pb1 O1 129.6(3) 1_666 1_656 ? N2 Pb1 O1 81.9(3) . 1_656 ? O2 Pb1 N1 132.4(3) 1_656 . ? O4 Pb1 N1 136.5(3) 1_666 . ? N2 Pb1 N1 82.0(3) . . ? O1 Pb1 N1 81.7(3) 1_656 . ? O2 Pb1 O3 129.5(3) 1_656 1_666 ? O4 Pb1 O3 50.3(3) 1_666 1_666 ? N2 Pb1 O3 78.3(3) . 1_666 ? O1 Pb1 O3 159.2(3) 1_656 1_666 ? N1 Pb1 O3 89.3(3) . 1_666 ? O2 Pb1 C17 26.1(3) 1_656 1_656 ? O4 Pb1 C17 105.2(3) 1_666 1_656 ? N2 Pb1 C17 81.2(3) . 1_656 ? O1 Pb1 C17 26.0(3) 1_656 1_656 ? N1 Pb1 C17 107.3(3) . 1_656 ? O3 Pb1 C17 151.5(3) 1_666 1_656 ? C10 N1 C6 116.9(11) . . ? C10 N1 Pb1 122.2(9) . . ? C6 N1 Pb1 115.1(9) . . ? C5 N2 C1 115.2(11) . . ? C5 N2 Pb1 116.1(8) . . ? C1 N2 Pb1 128.2(8) . . ? C17 O1 Pb1 87.6(7) . 1_454 ? C17 O2 Pb1 97.0(6) . 1_454 ? C18 O3 Pb1 87.5(7) . 1_444 ? C18 O4 Pb1 98.2(7) . 1_444 ? N2 C1 C2 125.6(11) . . ? N2 C1 H1 117.2 . . ? C2 C1 H1 117.2 . . ? C1 C2 C3 119.6(12) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 114.0(11) . . ? C2 C3 C3 124.1(14) . 2_767 ? C4 C3 C3 121.9(12) . 2_767 ? C5 C4 C3 123.0(10) . . ? C5 C4 H4 118.5 . . ? C3 C4 H4 118.5 . . ? N2 C5 C4 122.1(12) . . ? N2 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? N1 C6 C7 123.1(13) . . ? N1 C6 H6 118.5 . . ? C7 C6 H6 118.5 . . ? C6 C7 C8 120.7(12) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C9 C8 C7 115.7(11) . . ? C9 C8 C11 122.6(11) . . ? C7 C8 C11 121.7(10) . . ? C8 C9 C10 120.0(13) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? N1 C10 C9 123.6(13) . . ? N1 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? C16 C11 C12 117.8(10) . . ? C16 C11 C8 120.9(9) . . ? C12 C11 C8 121.3(10) . . ? C13 C12 C11 121.7(10) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C14 119.2(10) . . ? C12 C13 C17 119.9(10) . . ? C14 C13 C17 120.8(10) . . ? C15 C14 C13 120.1(10) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.5(10) . . ? C14 C15 C18 120.3(10) . . ? C16 C15 C18 120.3(10) . . ? C11 C16 C15 121.7(10) . . ? C11 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? O1 C17 O2 123.2(10) . . ? O1 C17 C13 119.3(10) . . ? O2 C17 C13 117.5(10) . . ? O1 C17 Pb1 66.3(6) . 1_454 ? O2 C17 Pb1 56.9(5) . 1_454 ? C13 C17 Pb1 173.6(8) . 1_454 ? O3 C18 O4 123.7(10) . . ? O3 C18 C15 118.9(10) . . ? O4 C18 C15 117.3(10) . . ? 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 O2 Pb1 N1 C10 -35.1(13) 1_656 . . . ? O4 Pb1 N1 C10 -163.6(10) 1_666 . . . ? N2 Pb1 N1 C10 -105.1(11) . . . . ? O1 Pb1 N1 C10 -22.2(11) 1_656 . . . ? O3 Pb1 N1 C10 176.6(11) 1_666 . . . ? C17 Pb1 N1 C10 -27.0(12) 1_656 . . . ? O2 Pb1 N1 C6 172.5(11) 1_656 . . . ? O4 Pb1 N1 C6 44.0(13) 1_666 . . . ? N2 Pb1 N1 C6 102.5(12) . . . . ? O1 Pb1 N1 C6 -174.6(12) 1_656 . . . ? O3 Pb1 N1 C6 24.2(12) 1_666 . . . ? C17 Pb1 N1 C6 -179.4(12) 1_656 . . . ? O2 Pb1 N2 C5 34.4(9) 1_656 . . . ? O4 Pb1 N2 C5 -47.6(9) 1_666 . . . ? O1 Pb1 N2 C5 87.1(9) 1_656 . . . ? N1 Pb1 N2 C5 169.8(10) . . . . ? O3 Pb1 N2 C5 -99.3(9) 1_666 . . . ? C17 Pb1 N2 C5 60.8(9) 1_656 . . . ? O2 Pb1 N2 C1 -154.2(12) 1_656 . . . ? O4 Pb1 N2 C1 123.8(12) 1_666 . . . ? O1 Pb1 N2 C1 -101.5(12) 1_656 . . . ? N1 Pb1 N2 C1 -18.8(12) . . . . ? O3 Pb1 N2 C1 72.1(12) 1_666 . . . ? C17 Pb1 N2 C1 -127.8(12) 1_656 . . . ? C5 N2 C1 C2 8(2) . . . . ? Pb1 N2 C1 C2 -163.7(13) . . . . ? N2 C1 C2 C3 -4(3) . . . . ? C1 C2 C3 C4 -1(2) . . . . ? C1 C2 C3 C3 179.6(16) . . . 2_767 ? C2 C3 C4 C5 2.8(18) . . . . ? C3 C3 C4 C5 -178.2(13) 2_767 . . . ? C1 N2 C5 C4 -6.1(19) . . . . ? Pb1 N2 C5 C4 166.4(10) . . . . ? C3 C4 C5 N2 1(2) . . . . ? C10 N1 C6 C7 2(3) . . . . ? Pb1 N1 C6 C7 156.3(16) . . . . ? N1 C6 C7 C8 -2(3) . . . . ? C6 C7 C8 C9 1(2) . . . . ? C6 C7 C8 C11 178.5(16) . . . . ? C7 C8 C9 C10 -2(2) . . . . ? C11 C8 C9 C10 -179.0(14) . . . . ? C6 N1 C10 C9 -3(3) . . . . ? Pb1 N1 C10 C9 -155.0(13) . . . . ? C8 C9 C10 N1 3(3) . . . . ? C9 C8 C11 C16 0.9(19) . . . . ? C7 C8 C11 C16 -175.9(13) . . . . ? C9 C8 C11 C12 178.6(13) . . . . ? C7 C8 C11 C12 1.7(19) . . . . ? C16 C11 C12 C13 0.2(17) . . . . ? C8 C11 C12 C13 -177.5(11) . . . . ? C11 C12 C13 C14 1.5(18) . . . . ? C11 C12 C13 C17 179.7(11) . . . . ? C12 C13 C14 C15 -3.3(18) . . . . ? C17 C13 C14 C15 178.5(11) . . . . ? C13 C14 C15 C16 3.5(17) . . . . ? C13 C14 C15 C18 -176.1(11) . . . . ? C12 C11 C16 C15 0.0(17) . . . . ? C8 C11 C16 C15 177.7(11) . . . . ? C14 C15 C16 C11 -1.8(17) . . . . ? C18 C15 C16 C11 177.8(10) . . . . ? Pb1 O1 C17 O2 3.0(12) 1_454 . . . ? Pb1 O1 C17 C13 -176.6(10) 1_454 . . . ? Pb1 O2 C17 O1 -3.2(14) 1_454 . . . ? Pb1 O2 C17 C13 176.3(9) 1_454 . . . ? C12 C13 C17 O1 -172.0(12) . . . . ? C14 C13 C17 O1 6.1(18) . . . . ? C12 C13 C17 O2 8.4(17) . . . . ? C14 C13 C17 O2 -173.5(11) . . . . ? C12 C13 C17 Pb1 37(8) . . . 1_454 ? C14 C13 C17 Pb1 -145(7) . . . 1_454 ? Pb1 O3 C18 O4 -5.2(13) 1_444 . . . ? Pb1 O3 C18 C15 171.3(10) 1_444 . . . ? Pb1 O4 C18 O3 5.7(14) 1_444 . . . ? Pb1 O4 C18 C15 -170.8(9) 1_444 . . . ? C14 C15 C18 O3 -4.9(18) . . . . ? C16 C15 C18 O3 175.5(12) . . . . ? C14 C15 C18 O4 171.8(11) . . . . ? C16 C15 C18 O4 -7.8(17) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 2.161 _refine_diff_density_min -2.344 _refine_diff_density_rms 0.228 _database_code_depnum_ccdc_archive 'CCDC 937605' ####################################################################### # # 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 ? _chemical_formula_sum 'C41 H0 Co N0 O0' _chemical_formula_weight 551.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 20.547(9) _cell_length_b 9.966(5) _cell_length_c 15.687(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.638(6) _cell_angle_gamma 90.00 _cell_volume 3167(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 0.566 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9011 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2967 _reflns_number_gt 2169 _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^)+(0.1469P)^2^+7.9065P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2967 _refine_ls_number_parameters 217 _refine_ls_number_restraints 534 _refine_ls_R_factor_all 0.1095 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.2438 _refine_ls_wR_factor_gt 0.2189 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.175 _refine_ls_shift/su_mean 0.011 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.136790(9) 1.0000 -0.111151(13) 0.02483(5) Uani 1 2 d S . . N1 N 0.14999(6) 1.0000 0.02928(9) 0.0354(4) Uani 1 2 d SU . . N2 N 0.12392(7) 1.0000 0.74840(9) 0.0497(5) Uani 1 2 d SU . . N3 N 0.12818(13) 1.0422(3) 0.43136(14) 0.0935(7) Uani 0.50 1 d PU . . N4 N 0.11320(10) 1.0000 0.33998(11) 0.0877(6) Uani 1 2 d SU . . N5 N 0.24286(6) 1.0000 -0.10707(8) 0.0306(3) Uani 1 2 d SU . . O2 O 0.06030(5) 0.85866(10) -0.11219(6) 0.0581(3) Uani 1 1 d U . . O3 O 0.15119(5) 0.75402(13) -0.11685(8) 0.0865(4) Uani 1 1 d U . . O4 O 0.3388(3) 0.0000 0.6005(5) 0.529(2) Uani 1 2 d SU A 1 H4 H 0.3601 0.0683 0.6146 0.794 Uiso 0.50 1 d PR A 1 O4' O 0.3083(3) 0.0000 0.4769(5) 0.531(2) Uani 1 2 d SU B 2 H5B H 0.3204 0.0000 0.5178 0.797 Uiso 1 2 d SR B 2 H5 H 0.3024 -0.0775 0.4598 0.797 Uiso 0.50 1 d PR B 2 C1 C 0.09058(6) 0.75327(14) -0.11504(8) 0.0455(4) Uani 1 1 d U . . C2 C 0.05479(5) 0.62066(12) -0.11620(7) 0.0344(3) Uani 1 1 d U . . C3 C -0.01278(5) 0.62023(11) -0.11406(8) 0.0334(3) Uani 1 1 d U . . H3 H -0.0350 0.7013 -0.1129 0.040 Uiso 1 1 calc R . . C4 C -0.04753(7) 0.5000 -0.11365(10) 0.0307(4) Uani 1 2 d SU . . C5 C -0.11902(7) 0.5000 -0.11075(10) 0.0309(4) Uani 1 2 d SU . . C6 C -0.15466(6) 0.61404(14) -0.10764(12) 0.0684(5) Uani 1 1 d U . . H6 H -0.1334 0.6966 -0.1062 0.082 Uiso 1 1 calc R . . C7 C 0.08713(7) 0.5000 -0.11771(11) 0.0369(5) Uani 1 2 d SU . . H7 H 0.1321 0.5000 -0.1198 0.044 Uiso 1 2 calc SR . . C8 C 0.27792(6) 1.11012(15) -0.10659(13) 0.0742(6) Uani 1 1 d U . . H8 H 0.2560 1.1916 -0.1055 0.089 Uiso 1 1 calc R . . C9 C 0.09628(8) 1.0000 0.06724(11) 0.0448(5) Uani 1 2 d SU . . H9 H 0.0553 1.0000 0.0315 0.054 Uiso 1 2 calc SR . . C10 C 0.09702(9) 1.0000 0.15473(11) 0.0503(5) Uani 1 2 d SU . . H10 H 0.0576 1.0000 0.1764 0.060 Uiso 1 2 calc SR . . C11 C 0.15597(10) 1.0000 0.20987(12) 0.0624(6) Uani 1 2 d SU . . C12 C 0.21341(11) 1.0000 0.17097(14) 0.0762(6) Uani 1 2 d SU . . H12 H 0.2549 1.0000 0.2054 0.091 Uiso 1 2 calc SR . . C13 C 0.20799(9) 1.0000 0.08325(13) 0.0589(5) Uani 1 2 d SU . . H13 H 0.2465 1.0000 0.0595 0.071 Uiso 1 2 calc SR . . C14 C 0.16178(12) 1.0000 0.30256(14) 0.0835(7) Uani 1 2 d SU . . H14 H 0.2037 1.0000 0.3358 0.100 Uiso 1 2 calc SR . . C15 C 0.10001(16) 1.0000 0.47285(16) 0.1035(7) Uani 1 2 d SU . . H15 H 0.0530 1.0000 0.4478 0.124 Uiso 1 2 calc SR . . C16 C 0.11013(14) 1.0000 0.56880(15) 0.0884(7) Uani 1 2 d SU . . C17 C 0.0680(2) 0.9291(5) 0.6108(2) 0.1004(9) Uani 0.50 1 d PU . . C18 C 0.07637(19) 0.9347(4) 0.7004(2) 0.0914(9) Uani 0.50 1 d PU . . C20 C 0.15062(18) 0.9143(5) 0.6154(2) 0.0912(8) Uani 0.50 1 d PU . . C21 C 0.15584(19) 1.0887(4) 0.7063(2) 0.0875(8) Uani 0.50 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01672(8) 0.02391(9) 0.03531(9) 0.000 0.00851(7) 0.000 N1 0.0269(6) 0.0383(7) 0.0421(6) 0.000 0.0089(5) 0.000 N2 0.0475(7) 0.0715(10) 0.0325(6) 0.000 0.0137(6) 0.000 N3 0.1058(12) 0.1309(16) 0.0484(9) 0.0050(11) 0.0263(9) -0.0128(13) N4 0.0848(10) 0.1403(13) 0.0400(8) 0.000 0.0162(8) 0.000 N5 0.0209(5) 0.0268(6) 0.0476(6) 0.000 0.0160(5) 0.000 O2 0.0683(5) 0.0417(5) 0.0645(5) -0.0028(4) 0.0118(4) -0.0246(4) O3 0.0375(5) 0.0939(8) 0.1259(9) 0.0253(7) 0.0076(5) -0.0329(5) O4 0.272(3) 0.965(4) 0.353(4) 0.000 0.061(3) 0.000 O4' 0.253(3) 0.976(5) 0.359(4) 0.000 0.035(4) 0.000 C1 0.0351(5) 0.0532(7) 0.0465(6) 0.0056(6) 0.0018(5) -0.0181(6) C2 0.0217(5) 0.0361(6) 0.0456(6) 0.0033(5) 0.0061(4) -0.0079(5) C3 0.0249(5) 0.0235(5) 0.0531(6) 0.0002(5) 0.0098(4) -0.0009(4) C4 0.0173(6) 0.0303(7) 0.0459(7) 0.000 0.0093(5) 0.000 C5 0.0223(6) 0.0224(7) 0.0493(8) 0.000 0.0103(6) 0.000 C6 0.0279(6) 0.0282(7) 0.1528(12) 0.0042(8) 0.0256(7) -0.0034(5) C7 0.0198(6) 0.0415(9) 0.0501(8) 0.000 0.0078(6) 0.000 C8 0.0238(5) 0.0380(7) 0.1643(14) -0.0055(9) 0.0262(7) 0.0051(6) C9 0.0276(7) 0.0694(10) 0.0389(7) 0.000 0.0095(6) 0.000 C10 0.0363(7) 0.0752(11) 0.0416(8) 0.000 0.0133(6) 0.000 C11 0.0485(8) 0.1005(12) 0.0396(8) 0.000 0.0108(7) 0.000 C12 0.0456(9) 0.1313(14) 0.0498(9) 0.000 0.0020(8) 0.000 C13 0.0314(7) 0.0956(12) 0.0517(8) 0.000 0.0128(7) 0.000 C14 0.0681(10) 0.1359(13) 0.0465(9) 0.000 0.0098(9) 0.000 C15 0.1100(13) 0.1450(14) 0.0546(10) 0.000 0.0114(11) 0.000 C16 0.0951(12) 0.1264(13) 0.0439(9) 0.000 0.0120(9) 0.000 C17 0.1169(15) 0.1199(15) 0.0596(13) -0.0007(13) 0.0005(13) -0.0225(14) C18 0.1046(15) 0.1123(16) 0.0525(12) -0.0008(13) -0.0006(13) -0.0243(14) C20 0.0979(14) 0.1315(15) 0.0459(12) -0.0106(13) 0.0169(12) 0.0053(14) C21 0.0986(14) 0.1214(16) 0.0423(12) 0.0091(13) 0.0111(12) -0.0202(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.1085(12) . ? Co1 O2 2.1085(12) 6_575 ? Co1 N5 2.1696(15) . ? Co1 N1 2.1740(17) . ? Co1 N2 2.1747(17) 1_554 ? N1 C9 1.339(2) . ? N1 C13 1.341(2) . ? N2 C18 1.303(4) . ? N2 C18 1.303(4) 6_575 ? N2 C21 1.339(4) 6_575 ? N2 C21 1.339(4) . ? N2 Co1 2.1747(17) 1_556 ? N3 N3 0.841(7) 6_575 ? N3 C15 1.030(4) . ? N3 N4 1.476(3) . ? N4 C14 1.240(3) . ? N4 N3 1.476(3) 6_575 ? N5 C8 1.3121(17) 6_575 ? N5 C8 1.3121(17) . ? O2 C1 1.2253(17) . ? O3 C1 1.2505(16) . ? O4 H4 0.8200 . ? O4 H5B 1.2883 . ? O4' H5B 0.6485 . ? O4' H5 0.8200 . ? C1 C2 1.5111(19) . ? C2 C7 1.3760(15) . ? C2 C3 1.3944(16) . ? C3 C4 1.3953(14) . ? C3 H3 0.9300 . ? C4 C3 1.3953(14) 6_565 ? C4 C5 1.477(2) . ? C5 C6 1.3573(17) 6_565 ? C5 C6 1.3573(17) . ? C6 C8 1.3887(19) 3_445 ? C6 H6 0.9300 . ? C7 C2 1.3760(15) 6_565 ? C7 H7 0.9300 . ? C8 C6 1.3887(19) 3 ? C8 H8 0.9300 . ? C9 C10 1.370(3) . ? C9 H9 0.9300 . ? C10 C11 1.366(3) . ? C10 H10 0.9300 . ? C11 C12 1.416(3) . ? C11 C14 1.439(3) . ? C12 C13 1.362(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 N3 1.030(4) 6_575 ? C15 C16 1.485(3) . ? C15 H15 0.9800 . ? C16 C20 1.323(4) 6_575 ? C16 C20 1.323(4) . ? C16 C17 1.369(5) . ? C16 C17 1.369(5) 6_575 ? C17 C18 1.389(5) . ? C17 C17 1.414(9) 6_575 ? C17 C20 1.694(6) . ? C17 C18 1.941(6) 6_575 ? C18 C18 1.302(8) 6_575 ? C18 C21 1.636(6) 6_575 ? C18 C17 1.941(6) 6_575 ? C20 C21 1.413(4) 6_575 ? C20 C20 1.707(10) 6_575 ? C21 C20 1.413(4) 6_575 ? C21 C18 1.637(6) 6_575 ? C21 C21 1.769(9) 6_575 ? 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 O2 Co1 O2 83.84(7) . 6_575 ? O2 Co1 N5 138.07(3) . . ? O2 Co1 N5 138.07(3) 6_575 . ? O2 Co1 N1 88.52(4) . . ? O2 Co1 N1 88.52(4) 6_575 . ? N5 Co1 N1 90.91(5) . . ? O2 Co1 N2 91.61(4) . 1_554 ? O2 Co1 N2 91.61(4) 6_575 1_554 ? N5 Co1 N2 88.92(5) . 1_554 ? N1 Co1 N2 179.82(5) . 1_554 ? C9 N1 C13 115.50(15) . . ? C9 N1 Co1 118.59(10) . . ? C13 N1 Co1 125.91(12) . . ? C18 N2 C18 59.9(4) . 6_575 ? C18 N2 C21 76.5(2) . 6_575 ? C18 N2 C21 115.3(2) 6_575 6_575 ? C18 N2 C21 115.3(2) . . ? C18 N2 C21 76.5(2) 6_575 . ? C21 N2 C21 82.7(4) 6_575 . ? C18 N2 Co1 122.51(19) . 1_556 ? C18 N2 Co1 122.51(19) 6_575 1_556 ? C21 N2 Co1 120.85(16) 6_575 1_556 ? C21 N2 Co1 120.85(16) . 1_556 ? N3 N3 C15 65.9(2) 6_575 . ? N3 N3 N4 73.45(13) 6_575 . ? C15 N3 N4 116.7(3) . . ? C14 N4 N3 114.0(2) . . ? C14 N4 N3 114.0(2) . 6_575 ? N3 N4 N3 33.1(3) . 6_575 ? C8 N5 C8 113.52(15) 6_575 . ? C8 N5 Co1 123.23(7) 6_575 . ? C8 N5 Co1 123.23(7) . . ? C1 O2 Co1 100.98(9) . . ? H4 O4 H5B 108.9 . . ? H5B O4' H5 109.6 . . ? O2 C1 O3 120.62(13) . . ? O2 C1 C2 120.07(11) . . ? O3 C1 C2 119.31(13) . . ? C7 C2 C3 118.90(11) . . ? C7 C2 C1 121.94(11) . . ? C3 C2 C1 119.14(10) . . ? C2 C3 C4 121.00(11) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C3 118.35(14) . 6_565 ? C3 C4 C5 120.82(7) . . ? C3 C4 C5 120.82(7) 6_565 . ? C6 C5 C6 113.72(16) 6_565 . ? C6 C5 C4 123.12(8) 6_565 . ? C6 C5 C4 123.12(8) . . ? C5 C6 C8 121.48(13) . 3_445 ? C5 C6 H6 119.3 . . ? C8 C6 H6 119.3 3_445 . ? C2 C7 C2 121.83(15) 6_565 . ? C2 C7 H7 119.1 6_565 . ? C2 C7 H7 119.1 . . ? N5 C8 C6 124.84(13) . 3 ? N5 C8 H8 117.6 . . ? C6 C8 H8 117.6 3 . ? N1 C9 C10 125.03(15) . . ? N1 C9 H9 117.5 . . ? C10 C9 H9 117.5 . . ? C11 C10 C9 119.63(18) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 116.22(18) . . ? C10 C11 C14 123.7(2) . . ? C12 C11 C14 120.08(18) . . ? C13 C12 C11 120.15(18) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N1 C13 C12 123.48(18) . . ? N1 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? N4 C14 C11 122.8(2) . . ? N4 C14 H14 118.6 . . ? C11 C14 H14 118.6 . . ? N3 C15 N3 48.2(4) 6_575 . ? N3 C15 C16 130.0(3) 6_575 . ? N3 C15 C16 130.0(3) . . ? N3 C15 H15 111.6 6_575 . ? N3 C15 H15 111.6 . . ? C16 C15 H15 111.6 . . ? C20 C16 C20 80.4(4) 6_575 . ? C20 C16 C17 117.2(3) 6_575 . ? C20 C16 C17 77.9(3) . . ? C20 C16 C17 77.9(3) 6_575 6_575 ? C20 C16 C17 117.2(3) . 6_575 ? C17 C16 C17 62.2(4) . 6_575 ? C20 C16 C15 121.9(2) 6_575 . ? C20 C16 C15 121.9(2) . . ? C17 C16 C15 119.7(2) . . ? C17 C16 C15 119.7(2) 6_575 . ? C16 C17 C18 119.0(3) . . ? C16 C17 C17 58.9(2) . 6_575 ? C18 C17 C17 87.7(3) . 6_575 ? C16 C17 C20 49.8(2) . . ? C18 C17 C20 90.4(3) . . ? C17 C17 C20 95.0(2) 6_575 . ? C16 C17 C18 90.0(3) . 6_575 ? C18 C17 C18 42.1(3) . 6_575 ? C17 C17 C18 45.62(17) 6_575 6_575 ? C20 C17 C18 93.6(3) . 6_575 ? C18 C18 N2 60.03(18) 6_575 . ? C18 C18 C17 92.3(3) 6_575 . ? N2 C18 C17 124.0(4) . . ? C18 C18 C21 98.2(2) 6_575 6_575 ? N2 C18 C21 52.7(2) . 6_575 ? C17 C18 C21 90.3(3) . 6_575 ? C18 C18 C17 45.62(17) 6_575 6_575 ? N2 C18 C17 92.1(3) . 6_575 ? C17 C18 C17 46.7(3) . 6_575 ? C21 C18 C17 96.2(3) 6_575 6_575 ? C16 C20 C21 120.4(4) . 6_575 ? C16 C20 C17 52.2(2) . . ? C21 C20 C17 87.2(3) 6_575 . ? C16 C20 C20 49.82(19) . 6_575 ? C21 C20 C20 91.2(3) 6_575 6_575 ? C17 C20 C20 85.0(2) . 6_575 ? N2 C21 C20 121.5(3) . 6_575 ? N2 C21 C18 50.8(2) . 6_575 ? C20 C21 C18 91.9(3) 6_575 6_575 ? N2 C21 C21 48.66(19) . 6_575 ? C20 C21 C21 88.8(3) 6_575 6_575 ? C18 C21 C21 81.8(2) 6_575 6_575 ? 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 O2 Co1 N1 C9 -41.93(3) . . . . ? O2 Co1 N1 C9 41.93(3) 6_575 . . . ? N5 Co1 N1 C9 180.0 . . . . ? N2 Co1 N1 C9 -180(6) 1_554 . . . ? O2 Co1 N1 C13 138.07(3) . . . . ? O2 Co1 N1 C13 -138.07(3) 6_575 . . . ? N5 Co1 N1 C13 0.0 . . . . ? N2 Co1 N1 C13 0(6) 1_554 . . . ? N3 N3 N4 C14 -97.59(9) 6_575 . . . ? C15 N3 N4 C14 -148.8(2) . . . . ? C15 N3 N4 N3 -51.2(3) . . . 6_575 ? O2 Co1 N5 C8 1.91(17) . . . 6_575 ? O2 Co1 N5 C8 179.50(12) 6_575 . . 6_575 ? N1 Co1 N5 C8 90.70(14) . . . 6_575 ? N2 Co1 N5 C8 -89.30(14) 1_554 . . 6_575 ? O2 Co1 N5 C8 -179.50(12) . . . . ? O2 Co1 N5 C8 -1.91(17) 6_575 . . . ? N1 Co1 N5 C8 -90.70(14) . . . . ? N2 Co1 N5 C8 89.30(14) 1_554 . . . ? O2 Co1 O2 C1 177.59(6) 6_575 . . . ? N5 Co1 O2 C1 -4.03(11) . . . . ? N1 Co1 O2 C1 -93.74(8) . . . . ? N2 Co1 O2 C1 86.15(8) 1_554 . . . ? Co1 O2 C1 O3 -0.31(14) . . . . ? Co1 O2 C1 C2 179.55(9) . . . . ? O2 C1 C2 C7 -178.73(13) . . . . ? O3 C1 C2 C7 1.13(19) . . . . ? O2 C1 C2 C3 0.05(17) . . . . ? O3 C1 C2 C3 179.92(12) . . . . ? C7 C2 C3 C4 -0.15(19) . . . . ? C1 C2 C3 C4 -178.97(12) . . . . ? C2 C3 C4 C3 1.0(2) . . . 6_565 ? C2 C3 C4 C5 179.56(13) . . . . ? C3 C4 C5 C6 -177.98(15) . . . 6_565 ? C3 C4 C5 C6 0.6(2) 6_565 . . 6_565 ? C3 C4 C5 C6 -0.6(2) . . . . ? C3 C4 C5 C6 177.98(15) 6_565 . . . ? C6 C5 C6 C8 -3.6(3) 6_565 . . 3_445 ? C4 C5 C6 C8 178.79(17) . . . 3_445 ? C3 C2 C7 C2 -0.7(2) . . . 6_565 ? C1 C2 C7 C2 178.06(10) . . . 6_565 ? C8 N5 C8 C6 1.5(3) 6_575 . . 3 ? Co1 N5 C8 C6 -177.18(14) . . . 3 ? C13 N1 C9 C10 0.0 . . . . ? Co1 N1 C9 C10 180.0 . . . . ? N1 C9 C10 C11 0.0 . . . . ? C9 C10 C11 C12 0.0 . . . . ? C9 C10 C11 C14 180.0 . . . . ? C10 C11 C12 C13 0.0 . . . . ? C14 C11 C12 C13 180.0 . . . . ? C9 N1 C13 C12 0.0 . . . . ? Co1 N1 C13 C12 180.0 . . . . ? C11 C12 C13 N1 0.0 . . . . ? N3 N4 C14 C11 -161.84(15) . . . . ? N3 N4 C14 C11 161.84(15) 6_575 . . . ? C10 C11 C14 N4 0.0 . . . . ? C12 C11 C14 N4 180.0 . . . . ? N4 N3 C15 N3 55.0(3) . . . 6_575 ? N3 N3 C15 C16 112.0(3) 6_575 . . . ? N4 N3 C15 C16 166.96(17) . . . . ? N3 C15 C16 C20 81.6(4) 6_575 . . 6_575 ? N3 C15 C16 C20 17.3(5) . . . 6_575 ? N3 C15 C16 C20 -17.3(5) 6_575 . . . ? N3 C15 C16 C20 -81.6(4) . . . . ? N3 C15 C16 C17 -111.4(4) 6_575 . . . ? N3 C15 C16 C17 -175.7(4) . . . . ? N3 C15 C16 C17 175.7(4) 6_575 . . 6_575 ? N3 C15 C16 C17 111.4(4) . . . 6_575 ? C20 C16 C17 C18 -9.7(5) 6_575 . . . ? C20 C16 C17 C18 62.7(4) . . . . ? C17 C16 C17 C18 -67.2(4) 6_575 . . . ? C15 C16 C17 C18 -177.3(3) . . . . ? C20 C16 C17 C17 57.5(2) 6_575 . . 6_575 ? C20 C16 C17 C17 129.9(2) . . . 6_575 ? C15 C16 C17 C17 -110.1(2) . . . 6_575 ? C20 C16 C17 C20 -72.4(4) 6_575 . . . ? C17 C16 C17 C20 -129.9(2) 6_575 . . . ? C15 C16 C17 C20 120.0(3) . . . . ? C20 C16 C17 C18 22.3(3) 6_575 . . 6_575 ? C20 C16 C17 C18 94.7(2) . . . 6_575 ? C17 C16 C17 C18 -35.2(2) 6_575 . . 6_575 ? C15 C16 C17 C18 -145.30(19) . . . 6_575 ? C21 N2 C18 C18 -130.2(2) 6_575 . . 6_575 ? C21 N2 C18 C18 -55.2(2) . . . 6_575 ? Co1 N2 C18 C18 111.6(2) 1_556 . . 6_575 ? C18 N2 C18 C17 70.6(4) 6_575 . . . ? C21 N2 C18 C17 -59.7(4) 6_575 . . . ? C21 N2 C18 C17 15.4(5) . . . . ? Co1 N2 C18 C17 -177.9(3) 1_556 . . . ? C18 N2 C18 C21 130.2(2) 6_575 . . 6_575 ? C21 N2 C18 C21 75.0(4) . . . 6_575 ? Co1 N2 C18 C21 -118.2(2) 1_556 . . 6_575 ? C18 N2 C18 C17 34.0(3) 6_575 . . 6_575 ? C21 N2 C18 C17 -96.2(3) 6_575 . . 6_575 ? C21 N2 C18 C17 -21.1(3) . . . 6_575 ? Co1 N2 C18 C17 145.60(15) 1_556 . . 6_575 ? C16 C17 C18 C18 52.2(3) . . . 6_575 ? C17 C17 C18 C18 0.000(2) 6_575 . . 6_575 ? C20 C17 C18 C18 95.0(2) . . . 6_575 ? C16 C17 C18 N2 -2.7(6) . . . . ? C17 C17 C18 N2 -54.8(4) 6_575 . . . ? C20 C17 C18 N2 40.1(5) . . . . ? C18 C17 C18 N2 -54.8(4) 6_575 . . . ? C16 C17 C18 C21 -46.0(4) . . . 6_575 ? C17 C17 C18 C21 -98.2(2) 6_575 . . 6_575 ? C20 C17 C18 C21 -3.3(3) . . . 6_575 ? C18 C17 C18 C21 -98.2(2) 6_575 . . 6_575 ? C16 C17 C18 C17 52.2(3) . . . 6_575 ? C20 C17 C18 C17 95.0(2) . . . 6_575 ? C18 C17 C18 C17 0.000(3) 6_575 . . 6_575 ? C20 C16 C20 C21 62.5(5) 6_575 . . 6_575 ? C17 C16 C20 C21 -58.2(4) . . . 6_575 ? C17 C16 C20 C21 -8.5(5) 6_575 . . 6_575 ? C15 C16 C20 C21 -175.8(3) . . . 6_575 ? C20 C16 C20 C17 120.7(3) 6_575 . . . ? C17 C16 C20 C17 49.7(4) 6_575 . . . ? C15 C16 C20 C17 -117.6(3) . . . . ? C17 C16 C20 C20 -120.7(3) . . . 6_575 ? C17 C16 C20 C20 -71.0(3) 6_575 . . 6_575 ? C15 C16 C20 C20 121.7(3) . . . 6_575 ? C18 C17 C20 C16 -129.0(4) . . . . ? C17 C17 C20 C16 -41.26(18) 6_575 . . . ? C18 C17 C20 C16 -87.0(3) 6_575 . . . ? C16 C17 C20 C21 132.8(4) . . . 6_575 ? C18 C17 C20 C21 3.8(4) . . . 6_575 ? C17 C17 C20 C21 91.5(3) 6_575 . . 6_575 ? C18 C17 C20 C21 45.8(3) 6_575 . . 6_575 ? C16 C17 C20 C20 41.26(18) . . . 6_575 ? C18 C17 C20 C20 -87.7(3) . . . 6_575 ? C17 C17 C20 C20 0.0 6_575 . . 6_575 ? C18 C17 C20 C20 -45.73(17) 6_575 . . 6_575 ? C18 N2 C21 C20 -16.3(5) . . . 6_575 ? C18 N2 C21 C20 -63.2(4) 6_575 . . 6_575 ? C21 N2 C21 C20 55.0(4) 6_575 . . 6_575 ? Co1 N2 C21 C20 176.7(3) 1_556 . . 6_575 ? C18 N2 C21 C18 46.9(3) . . . 6_575 ? C21 N2 C21 C18 118.3(2) 6_575 . . 6_575 ? Co1 N2 C21 C18 -120.0(2) 1_556 . . 6_575 ? C18 N2 C21 C21 -71.3(2) . . . 6_575 ? C18 N2 C21 C21 -118.3(2) 6_575 . . 6_575 ? Co1 N2 C21 C21 121.7(2) 1_556 . . 6_575 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.805 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 937606' ####################################################################### # # 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 ? _chemical_formula_sum 'C19 H13 Co N3 O9' _chemical_formula_weight 486.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.94(2) _cell_length_b 10.51(2) _cell_length_c 10.98(2) _cell_angle_alpha 74.51(3) _cell_angle_beta 67.11(3) _cell_angle_gamma 74.83(3) _cell_volume 1002(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 494 _exptl_absorpt_coefficient_mu 0.916 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8310 _exptl_absorpt_correction_T_max 0.8381 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5671 _diffrn_reflns_av_R_equivalents 0.1239 _diffrn_reflns_av_sigmaI/netI 0.3266 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3465 _reflns_number_gt 1183 _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^)+(0.0633P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3465 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2175 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.818 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.61818(16) 0.14030(15) 0.68745(13) 0.0360(5) Uani 1 1 d . . . N1 N -0.2630(9) 0.1475(8) 1.4773(7) 0.036(2) Uani 1 1 d . . . N2 N 0.6507(9) -0.0705(8) 0.7242(8) 0.038(2) Uani 1 1 d . . . N3 N 0.6130(9) -0.2791(9) 0.8149(8) 0.045(2) Uani 1 1 d . . . O1 O 0.4085(7) 0.1542(7) 0.6734(6) 0.0444(14) Uani 1 1 d . . . O2 O 0.4212(7) 0.1390(7) 0.8710(6) 0.0444(14) Uani 1 1 d . . . O3 O -0.2432(7) 0.1460(7) 0.7781(6) 0.0426(19) Uani 1 1 d . . . O4 O -0.1059(10) 0.2915(10) 0.6312(8) 0.094(3) Uani 1 1 d . . . O5 O 0.5684(9) 0.3578(7) 0.6425(8) 0.070(2) Uani 1 1 d . . . H5 H 0.6456 0.3877 0.6137 0.106 Uiso 1 1 calc R . . O6 O 0.294(2) 0.491(2) 0.607(4) 0.44(3) Uani 1 1 d . . . O8 O 0.070(4) 0.4948(19) 0.574(2) 0.342(14) Uani 1 1 d . . . C1 C 0.3402(11) 0.1542(9) 0.8015(10) 0.034(3) Uani 1 1 d . . . C2 C 0.1807(10) 0.1629(9) 0.8585(9) 0.028(2) Uani 1 1 d . . . C3 C 0.1106(11) 0.1498(9) 0.9951(9) 0.034(3) Uani 1 1 d . . . H3 H 0.1666 0.1350 1.0501 0.041 Uiso 1 1 calc R . . C4 C -0.0422(10) 0.1583(9) 1.0528(9) 0.028(2) Uani 1 1 d . . . C5 C -0.1226(10) 0.1748(9) 0.9683(9) 0.033(3) Uani 1 1 d . . . H5A H -0.2242 0.1754 1.0057 0.039 Uiso 1 1 calc R . . C6 C -0.0547(10) 0.1904(10) 0.8305(9) 0.033(3) Uani 1 1 d . . . C7 C 0.0947(11) 0.1866(9) 0.7803(9) 0.033(3) Uani 1 1 d . . . H7 H 0.1411 0.2010 0.6874 0.040 Uiso 1 1 calc R . . C8 C -0.1415(12) 0.2109(12) 0.7401(10) 0.043(3) Uani 1 1 d . . . C9 C -0.1199(11) 0.1529(10) 1.2024(9) 0.036(3) Uani 1 1 d . . . C10 C -0.2667(14) 0.1594(13) 1.2605(10) 0.075(4) Uani 1 1 d . . . H10 H -0.3230 0.1640 1.2082 0.090 Uiso 1 1 calc R . . C11 C -0.3371(13) 0.1595(14) 1.3979(10) 0.077(4) Uani 1 1 d . . . H11 H -0.4399 0.1683 1.4342 0.093 Uiso 1 1 calc R . . C12 C -0.1201(12) 0.1395(12) 1.4224(10) 0.055(3) Uani 1 1 d . . . H12 H -0.0665 0.1351 1.4769 0.066 Uiso 1 1 calc R . . C13 C -0.0428(13) 0.1373(12) 1.2862(10) 0.062(4) Uani 1 1 d . . . H13 H 0.0603 0.1253 1.2528 0.074 Uiso 1 1 calc R . . C14 C 0.5945(11) -0.1521(10) 0.8313(10) 0.039(3) Uani 1 1 d . . . H14 H 0.5445 -0.1259 0.9144 0.047 Uiso 1 1 calc R . . C15 C 0.7208(14) -0.1542(12) 0.6237(11) 0.067(4) Uani 1 1 d . . . H15 H 0.7761 -0.1262 0.5342 0.081 Uiso 1 1 calc R . . C16 C 0.6935(14) -0.2790(12) 0.6800(10) 0.069(4) Uani 1 1 d . . . H16 H 0.7231 -0.3516 0.6365 0.082 Uiso 1 1 calc R . . C17 C 0.5025(14) -0.3926(11) 1.0404(10) 0.069(3) Uani 1 1 d . . . H17 H 0.5026 -0.3192 1.0724 0.082 Uiso 1 1 calc R . . C18 C 0.5579(15) -0.3908(12) 0.9097(11) 0.069(3) Uani 1 1 d . . . C19 C 0.5555(18) -0.4996(13) 0.8693(11) 0.103(6) Uani 1 1 d . . . H19 H 0.5941 -0.5024 0.7779 0.124 Uiso 1 1 calc R . . O7 O 0.988(3) 0.5156(18) 0.899(2) 0.38(2) Uani 1 1 d . . . O7' O 0.205(4) 0.487(2) 0.807(5) 0.49(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0361(9) 0.0531(11) 0.0190(7) -0.0197(6) 0.0014(6) -0.0116(7) N1 0.035(6) 0.045(6) 0.026(5) -0.014(4) -0.004(4) -0.005(4) N2 0.048(6) 0.040(6) 0.028(5) -0.004(4) -0.014(5) -0.012(5) N3 0.057(6) 0.045(6) 0.031(5) -0.017(5) -0.006(5) -0.010(5) O1 0.038(3) 0.074(4) 0.022(3) -0.029(3) 0.001(2) -0.008(3) O2 0.038(3) 0.074(4) 0.022(3) -0.029(3) 0.001(2) -0.008(3) O3 0.028(4) 0.063(5) 0.043(4) -0.027(4) -0.010(4) -0.005(4) O4 0.104(8) 0.144(9) 0.052(5) 0.016(6) -0.037(6) -0.071(7) O5 0.105(7) 0.065(6) 0.051(5) -0.013(4) -0.032(6) -0.020(5) O6 0.143(17) 0.23(2) 0.67(6) 0.12(3) 0.03(3) -0.070(15) O8 0.58(5) 0.197(18) 0.34(3) -0.070(17) -0.30(3) 0.02(2) C1 0.032(7) 0.038(7) 0.040(6) -0.009(5) -0.016(5) -0.013(5) C2 0.011(5) 0.047(7) 0.034(6) -0.021(5) -0.005(5) -0.010(5) C3 0.035(7) 0.051(7) 0.023(5) -0.021(5) -0.004(5) -0.012(5) C4 0.020(6) 0.035(6) 0.032(6) -0.010(5) -0.009(5) -0.003(5) C5 0.022(6) 0.049(7) 0.026(5) -0.017(5) 0.001(5) -0.007(5) C6 0.015(6) 0.059(7) 0.030(5) -0.019(5) -0.002(5) -0.013(5) C7 0.041(7) 0.033(6) 0.030(5) -0.009(5) -0.012(5) -0.010(5) C8 0.029(7) 0.070(9) 0.032(6) -0.020(6) -0.010(6) -0.003(6) C9 0.036(7) 0.052(7) 0.021(5) -0.013(5) -0.002(5) -0.019(6) C10 0.052(9) 0.149(13) 0.035(7) -0.038(8) 0.000(7) -0.037(9) C11 0.032(8) 0.177(14) 0.029(6) -0.036(8) -0.008(6) -0.014(8) C12 0.028(7) 0.114(11) 0.031(6) -0.025(6) -0.007(6) -0.018(7) C13 0.038(7) 0.111(11) 0.028(6) -0.031(7) 0.002(6) -0.002(7) C14 0.059(8) 0.030(7) 0.031(6) -0.014(5) -0.012(6) -0.009(6) C15 0.098(10) 0.054(9) 0.038(7) -0.031(6) 0.013(7) -0.026(8) C16 0.101(11) 0.052(9) 0.033(6) -0.030(6) 0.021(7) -0.027(8) C17 0.116(8) 0.054(5) 0.038(4) -0.028(5) -0.001(5) -0.037(5) C18 0.116(8) 0.054(5) 0.038(4) -0.028(5) -0.001(5) -0.037(5) C19 0.210(17) 0.074(10) 0.026(6) -0.005(7) -0.003(9) -0.089(11) O7 0.41(3) 0.143(15) 0.37(3) -0.10(2) 0.15(4) -0.085(19) O7' 0.40(5) 0.125(17) 0.89(9) -0.11(3) -0.14(5) -0.08(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O3 2.009(7) 1_655 ? Co1 N2 2.104(9) . ? Co1 O1 2.114(8) . ? Co1 N1 2.135(8) 1_654 ? Co1 O5 2.170(9) . ? Co1 O2 2.197(7) . ? N1 C12 1.298(12) . ? N1 C11 1.308(12) . ? N1 Co1 2.135(8) 1_456 ? N2 C14 1.278(11) . ? N2 C15 1.440(12) . ? N3 C14 1.350(11) . ? N3 C16 1.383(11) . ? N3 C18 1.415(12) . ? O1 C1 1.303(11) . ? O2 C1 1.265(10) . ? O3 C8 1.242(11) . ? O3 Co1 2.009(7) 1_455 ? O4 C8 1.248(12) . ? O5 H5 0.8200 . ? C1 C2 1.448(12) . ? C2 C7 1.369(12) . ? C2 C3 1.371(12) . ? C3 C4 1.388(12) . ? C3 H3 0.9300 . ? C4 C5 1.396(12) . ? C4 C9 1.511(12) . ? C5 C6 1.379(12) . ? C5 H5A 0.9300 . ? C6 C7 1.362(12) . ? C6 C8 1.494(13) . ? C7 H7 0.9300 . ? C9 C10 1.337(14) . ? C9 C13 1.365(13) . ? C10 C11 1.395(14) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.394(13) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.341(13) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.318(14) . ? C17 C19 1.377(13) 2_647 ? C17 H17 0.9300 . ? C18 C19 1.342(13) . ? C19 C17 1.377(13) 2_647 ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Co1 N2 94.4(3) 1_655 . ? O3 Co1 O1 155.1(2) 1_655 . ? N2 Co1 O1 91.0(3) . . ? O3 Co1 N1 109.3(3) 1_655 1_654 ? N2 Co1 N1 91.6(3) . 1_654 ? O1 Co1 N1 94.9(3) . 1_654 ? O3 Co1 O5 91.0(3) 1_655 . ? N2 Co1 O5 174.6(3) . . ? O1 Co1 O5 83.8(3) . . ? N1 Co1 O5 87.2(3) 1_654 . ? O3 Co1 O2 94.9(3) 1_655 . ? N2 Co1 O2 88.8(3) . . ? O1 Co1 O2 60.8(3) . . ? N1 Co1 O2 155.7(3) 1_654 . ? O5 Co1 O2 90.1(3) . . ? C12 N1 C11 117.3(9) . . ? C12 N1 Co1 124.0(7) . 1_456 ? C11 N1 Co1 118.7(7) . 1_456 ? C14 N2 C15 103.4(8) . . ? C14 N2 Co1 129.7(7) . . ? C15 N2 Co1 126.0(7) . . ? C14 N3 C16 105.5(8) . . ? C14 N3 C18 129.3(8) . . ? C16 N3 C18 125.1(9) . . ? C1 O1 Co1 92.6(6) . . ? C1 O2 Co1 89.9(5) . . ? C8 O3 Co1 130.6(7) . 1_455 ? Co1 O5 H5 109.5 . . ? O2 C1 O1 116.4(8) . . ? O2 C1 C2 123.5(9) . . ? O1 C1 C2 120.0(9) . . ? C7 C2 C3 117.8(9) . . ? C7 C2 C1 122.3(9) . . ? C3 C2 C1 119.9(9) . . ? C2 C3 C4 121.3(9) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 118.1(8) . . ? C3 C4 C9 121.1(9) . . ? C5 C4 C9 120.8(8) . . ? C6 C5 C4 121.5(9) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C7 C6 C5 117.2(9) . . ? C7 C6 C8 121.4(9) . . ? C5 C6 C8 121.4(9) . . ? C6 C7 C2 123.9(9) . . ? C6 C7 H7 118.0 . . ? C2 C7 H7 118.0 . . ? O3 C8 O4 124.7(10) . . ? O3 C8 C6 117.7(10) . . ? O4 C8 C6 117.6(10) . . ? C10 C9 C13 116.4(10) . . ? C10 C9 C4 122.2(10) . . ? C13 C9 C4 121.5(9) . . ? C9 C10 C11 121.3(11) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? N1 C11 C10 122.0(11) . . ? N1 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? N1 C12 C13 123.6(10) . . ? N1 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C9 C13 C12 119.3(11) . . ? C9 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? N2 C14 N3 115.0(9) . . ? N2 C14 H14 122.5 . . ? N3 C14 H14 122.5 . . ? C16 C15 N2 109.1(9) . . ? C16 C15 H15 125.5 . . ? N2 C15 H15 125.5 . . ? C15 C16 N3 107.0(9) . . ? C15 C16 H16 126.5 . . ? N3 C16 H16 126.5 . . ? C18 C17 C19 121.8(10) . 2_647 ? C18 C17 H17 119.1 . . ? C19 C17 H17 119.1 2_647 . ? C17 C18 C19 116.6(11) . . ? C17 C18 N3 122.7(10) . . ? C19 C18 N3 120.7(10) . . ? C18 C19 C17 121.7(10) . 2_647 ? C18 C19 H19 119.2 . . ? C17 C19 H19 119.2 2_647 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Co1 N2 C14 79.4(9) 1_655 . . . ? O1 Co1 N2 C14 -76.2(9) . . . . ? N1 Co1 N2 C14 -171.1(9) 1_654 . . . ? O5 Co1 N2 C14 -94(4) . . . . ? O2 Co1 N2 C14 -15.4(9) . . . . ? O3 Co1 N2 C15 -113.8(9) 1_655 . . . ? O1 Co1 N2 C15 90.6(9) . . . . ? N1 Co1 N2 C15 -4.3(9) 1_654 . . . ? O5 Co1 N2 C15 73(4) . . . . ? O2 Co1 N2 C15 151.4(9) . . . . ? O3 Co1 O1 C1 -12.2(10) 1_655 . . . ? N2 Co1 O1 C1 90.4(5) . . . . ? N1 Co1 O1 C1 -177.9(5) 1_654 . . . ? O5 Co1 O1 C1 -91.2(6) . . . . ? O2 Co1 O1 C1 2.3(5) . . . . ? O3 Co1 O2 C1 171.5(5) 1_655 . . . ? N2 Co1 O2 C1 -94.2(6) . . . . ? O1 Co1 O2 C1 -2.4(5) . . . . ? N1 Co1 O2 C1 -2.9(10) 1_654 . . . ? O5 Co1 O2 C1 80.5(6) . . . . ? Co1 O2 C1 O1 3.8(8) . . . . ? Co1 O2 C1 C2 179.9(8) . . . . ? Co1 O1 C1 O2 -3.9(8) . . . . ? Co1 O1 C1 C2 179.8(7) . . . . ? O2 C1 C2 C7 176.4(9) . . . . ? O1 C1 C2 C7 -7.6(14) . . . . ? O2 C1 C2 C3 -2.3(14) . . . . ? O1 C1 C2 C3 173.7(9) . . . . ? C7 C2 C3 C4 0.9(14) . . . . ? C1 C2 C3 C4 179.7(8) . . . . ? C2 C3 C4 C5 2.7(14) . . . . ? C2 C3 C4 C9 -175.9(9) . . . . ? C3 C4 C5 C6 -3.7(14) . . . . ? C9 C4 C5 C6 174.9(8) . . . . ? C4 C5 C6 C7 1.1(14) . . . . ? C4 C5 C6 C8 -178.7(9) . . . . ? C5 C6 C7 C2 2.8(14) . . . . ? C8 C6 C7 C2 -177.4(9) . . . . ? C3 C2 C7 C6 -3.8(14) . . . . ? C1 C2 C7 C6 177.4(9) . . . . ? Co1 O3 C8 O4 1.0(17) 1_455 . . . ? Co1 O3 C8 C6 -178.5(6) 1_455 . . . ? C7 C6 C8 O3 141.2(10) . . . . ? C5 C6 C8 O3 -39.0(14) . . . . ? C7 C6 C8 O4 -38.4(15) . . . . ? C5 C6 C8 O4 141.4(11) . . . . ? C3 C4 C9 C10 -179.3(10) . . . . ? C5 C4 C9 C10 2.1(16) . . . . ? C3 C4 C9 C13 -1.1(15) . . . . ? C5 C4 C9 C13 -179.7(10) . . . . ? C13 C9 C10 C11 4.2(19) . . . . ? C4 C9 C10 C11 -177.5(11) . . . . ? C12 N1 C11 C10 2.1(19) . . . . ? Co1 N1 C11 C10 -177.3(10) 1_456 . . . ? C9 C10 C11 N1 -3(2) . . . . ? C11 N1 C12 C13 -2.9(17) . . . . ? Co1 N1 C12 C13 176.5(9) 1_456 . . . ? C10 C9 C13 C12 -4.9(17) . . . . ? C4 C9 C13 C12 176.9(9) . . . . ? N1 C12 C13 C9 4.4(19) . . . . ? C15 N2 C14 N3 -2.4(12) . . . . ? Co1 N2 C14 N3 166.7(6) . . . . ? C16 N3 C14 N2 1.0(13) . . . . ? C18 N3 C14 N2 -175.9(11) . . . . ? C14 N2 C15 C16 2.9(13) . . . . ? Co1 N2 C15 C16 -166.7(9) . . . . ? N2 C15 C16 N3 -2.3(14) . . . . ? C14 N3 C16 C15 0.9(13) . . . . ? C18 N3 C16 C15 178.1(11) . . . . ? C19 C17 C18 C19 0(3) 2_647 . . . ? C19 C17 C18 N3 177.6(13) 2_647 . . . ? C14 N3 C18 C17 -15(2) . . . . ? C16 N3 C18 C17 168.9(14) . . . . ? C14 N3 C18 C19 163.2(13) . . . . ? C16 N3 C18 C19 -13(2) . . . . ? C17 C18 C19 C17 0(3) . . . 2_647 ? N3 C18 C19 C17 -177.6(13) . . . 2_647 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.648 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 937607'