# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C27 H20 Co N3 O4), H2 O' _chemical_formula_sum 'C54 H42 Co2 N6 O9' _chemical_formula_weight 1036.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.201(14) _cell_length_b 9.992(7) _cell_length_c 21.796(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.234(12) _cell_angle_gamma 90.00 _cell_volume 4399(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2151 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 22.83 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_absorpt_coefficient_mu 0.825 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9074 _exptl_absorpt_correction_T_max 0.9369 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10535 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3867 _reflns_number_gt 2701 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+5.3023P] 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 3867 _refine_ls_number_parameters 326 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 C1 C 0.7515(2) 0.0316(5) 0.59090(18) 0.0447(11) Uani 1 1 d . . . C2 C 0.68819(18) -0.0374(4) 0.57313(17) 0.0368(9) Uani 1 1 d . . . C3 C 0.62965(19) 0.0310(4) 0.57530(19) 0.0451(10) Uani 1 1 d . . . H3 H 0.6297 0.1215 0.5853 0.054 Uiso 1 1 calc R . . C4 C 0.57082(19) -0.0332(4) 0.5628(2) 0.0466(11) Uani 1 1 d . . . H4 H 0.5312 0.0133 0.5661 0.056 Uiso 1 1 calc R . . C5 C 0.56973(18) -0.1641(4) 0.54553(17) 0.0361(9) Uani 1 1 d . . . C6 C 0.62878(19) -0.2309(4) 0.5411(2) 0.0471(11) Uani 1 1 d . . . H6 H 0.6291 -0.3196 0.5281 0.057 Uiso 1 1 calc R . . C7 C 0.68743(19) -0.1679(5) 0.5557(2) 0.0488(11) Uani 1 1 d . . . H7 H 0.7270 -0.2150 0.5537 0.059 Uiso 1 1 calc R . . C8 C 0.50647(17) -0.2334(4) 0.53323(17) 0.0323(9) Uani 1 1 d . . . C9 C 0.49467(18) -0.3039(4) 0.48046(17) 0.0369(9) Uani 1 1 d . . . H9 H 0.5278 -0.3114 0.4517 0.044 Uiso 1 1 calc R . . C10 C 0.43457(17) -0.3635(4) 0.46957(16) 0.0321(8) Uani 1 1 d . . . C11 C 0.38976(17) -0.3562(4) 0.51605(17) 0.0339(9) Uani 1 1 d . . . H11 H 0.3492 -0.3991 0.5103 0.041 Uiso 1 1 calc R . . C12 C 0.45803(18) -0.2282(4) 0.57567(18) 0.0366(9) Uani 1 1 d . . . H12 H 0.4654 -0.1781 0.6111 0.044 Uiso 1 1 calc R . . C13 C 0.41684(17) -0.4328(4) 0.41210(17) 0.0343(9) Uani 1 1 d . . . C14 C 0.46309(19) -0.4982(4) 0.37859(18) 0.0435(10) Uani 1 1 d . . . H14 H 0.5066 -0.5020 0.3933 0.052 Uiso 1 1 calc R . . C15 C 0.4468(2) -0.5582(5) 0.32382(19) 0.0490(11) Uani 1 1 d . . . H15 H 0.4792 -0.6014 0.3014 0.059 Uiso 1 1 calc R . . C16 C 0.3825(2) -0.5541(4) 0.30218(18) 0.0428(10) Uani 1 1 d . . . C17 C 0.3640(2) -0.6130(4) 0.2412(2) 0.0474(11) Uani 1 1 d . . . C18 C 0.3362(2) -0.4902(4) 0.33549(18) 0.0448(11) Uani 1 1 d . . . H18 H 0.2925 -0.4888 0.3213 0.054 Uiso 1 1 calc R . . C19 C 0.35271(19) -0.4276(4) 0.38974(19) 0.0427(10) Uani 1 1 d . . . H19 H 0.3206 -0.3818 0.4113 0.051 Uiso 1 1 calc R . . C20 C 0.8384(3) 0.4384(5) 0.7622(2) 0.0664(14) Uani 1 1 d . . . H20A H 0.8122 0.3587 0.7656 0.100 Uiso 1 1 calc R . . H20B H 0.8201 0.5076 0.7872 0.100 Uiso 1 1 calc R . . H20C H 0.8830 0.4200 0.7758 0.100 Uiso 1 1 calc R . . C21 C 0.83824(18) 0.4825(4) 0.69770(18) 0.0405(10) Uani 1 1 d . . . C22 C 0.8302(2) 0.4901(5) 0.60040(19) 0.0447(10) Uani 1 1 d . . . H22 H 0.8254 0.4638 0.5596 0.054 Uiso 1 1 calc R . . C23 C 0.8373(2) 0.6148(5) 0.6187(2) 0.0527(12) Uani 1 1 d . . . H23 H 0.8387 0.6906 0.5940 0.063 Uiso 1 1 calc R . . C24 C 0.8603(2) 0.7221(4) 0.7205(3) 0.0634(14) Uani 1 1 d . . . H24A H 0.8358 0.7167 0.7582 0.076 Uiso 1 1 calc R . . H24B H 0.8487 0.8055 0.7002 0.076 Uiso 1 1 calc R . . C25 C 0.9337(2) 0.7207(4) 0.7354(3) 0.0577(13) Uani 1 1 d . . . C26 C 0.9785(3) 0.7189(10) 0.6934(3) 0.153(4) Uani 1 1 d . . . H26 H 0.9652 0.7170 0.6524 0.184 Uiso 1 1 calc R . . C27 C 0.9559(3) 0.7198(10) 0.7922(3) 0.150(4) Uani 1 1 d . . . H27 H 0.9256 0.7197 0.8237 0.180 Uiso 1 1 calc R . . Co1 Co 0.83343(2) 0.20212(5) 0.63909(2) 0.03305(19) Uani 1 1 d . . . N1 N 0.84217(16) 0.6104(3) 0.68081(17) 0.0467(9) Uani 1 1 d . . . N2 N 0.83084(14) 0.4048(3) 0.64905(13) 0.0348(8) Uani 1 1 d . . . N3 N 0.40051(14) -0.2921(3) 0.56833(14) 0.0345(7) Uani 1 1 d . . . O1 O 0.74918(13) 0.1561(3) 0.59696(13) 0.0509(8) Uani 1 1 d . . . O2 O 0.80231(14) -0.0345(3) 0.59953(15) 0.0618(9) Uani 1 1 d . . . O3 O 0.40581(16) -0.6553(4) 0.20698(14) 0.0716(11) Uani 1 1 d . . . O4 O 0.30487(17) -0.6219(4) 0.22659(15) 0.0701(10) Uani 1 1 d . . . O1W O 0.5000 0.1178(19) 0.2500 0.0435(9) Uani 1 2 d SD . . H1W H 0.5000 0.1999(19) 0.2500 0.080 Uiso 1 2 d SD . . H2W H 0.497(6) 0.0836(19) 0.2841(4) 0.080 Uiso 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.041(2) 0.063(3) 0.030(2) 0.009(2) -0.0035(18) -0.016(2) C2 0.034(2) 0.046(3) 0.030(2) 0.0040(18) -0.0021(16) -0.0140(18) C3 0.042(2) 0.035(2) 0.058(3) -0.005(2) -0.008(2) -0.0078(19) C4 0.032(2) 0.042(3) 0.066(3) -0.002(2) -0.004(2) -0.0042(18) C5 0.033(2) 0.042(2) 0.033(2) 0.0014(17) -0.0033(16) -0.0084(17) C6 0.038(2) 0.039(3) 0.065(3) -0.009(2) 0.003(2) -0.0088(19) C7 0.030(2) 0.056(3) 0.060(3) -0.002(2) 0.000(2) -0.0014(19) C8 0.0306(19) 0.033(2) 0.033(2) 0.0003(16) -0.0023(16) -0.0057(16) C9 0.032(2) 0.043(2) 0.036(2) -0.0028(18) 0.0004(16) -0.0035(18) C10 0.033(2) 0.032(2) 0.031(2) -0.0009(16) -0.0004(16) -0.0018(17) C11 0.0271(19) 0.037(2) 0.038(2) -0.0006(18) -0.0013(16) -0.0072(16) C12 0.034(2) 0.038(2) 0.038(2) -0.0077(17) -0.0042(17) -0.0035(17) C13 0.0313(19) 0.039(2) 0.032(2) -0.0043(17) -0.0012(16) -0.0028(17) C14 0.033(2) 0.053(3) 0.044(2) -0.008(2) -0.0061(18) -0.0028(18) C15 0.045(2) 0.062(3) 0.040(2) -0.014(2) 0.0041(19) 0.007(2) C16 0.049(2) 0.045(3) 0.034(2) -0.0063(19) -0.0018(19) -0.002(2) C17 0.057(3) 0.041(3) 0.044(3) -0.006(2) -0.008(2) -0.009(2) C18 0.036(2) 0.058(3) 0.039(2) -0.007(2) -0.0074(19) -0.0049(19) C19 0.035(2) 0.051(3) 0.041(2) -0.009(2) 0.0019(18) -0.0032(19) C20 0.099(4) 0.064(3) 0.036(3) -0.009(2) -0.009(3) 0.010(3) C21 0.035(2) 0.044(3) 0.042(2) -0.0027(19) -0.0061(18) 0.0034(18) C22 0.044(2) 0.055(3) 0.035(2) 0.004(2) -0.0004(19) 0.004(2) C23 0.046(3) 0.053(3) 0.058(3) 0.013(2) -0.001(2) 0.003(2) C24 0.061(3) 0.038(3) 0.090(4) -0.015(2) -0.025(3) 0.009(2) C25 0.059(3) 0.031(3) 0.082(4) -0.007(2) -0.023(3) 0.003(2) C26 0.069(4) 0.296(12) 0.093(5) 0.110(7) -0.034(4) -0.075(6) C27 0.061(4) 0.297(12) 0.091(5) -0.111(6) -0.027(4) 0.060(5) Co1 0.0283(3) 0.0420(3) 0.0287(3) 0.0002(2) -0.0031(2) -0.0049(2) N1 0.0414(19) 0.041(2) 0.058(2) -0.0037(17) -0.0115(17) 0.0033(16) N2 0.0314(16) 0.043(2) 0.0301(18) -0.0014(14) -0.0032(14) -0.0032(14) N3 0.0278(16) 0.044(2) 0.0316(17) -0.0071(15) 0.0000(13) -0.0069(14) O1 0.0444(17) 0.054(2) 0.0534(19) -0.0044(15) -0.0088(14) -0.0181(14) O2 0.0382(17) 0.073(2) 0.074(2) 0.0168(18) -0.0087(16) -0.0148(16) O3 0.066(2) 0.105(3) 0.0449(19) -0.0330(19) 0.0183(17) -0.034(2) O4 0.074(2) 0.076(2) 0.058(2) -0.0277(18) -0.0286(18) 0.0272(19) O1W 0.053(2) 0.0377(19) 0.0353(17) -0.0028(13) 0.0009(15) 0.0141(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.231(5) . ? C1 O1 1.252(5) . ? C1 C2 1.497(5) . ? C2 C7 1.358(6) . ? C2 C3 1.368(6) . ? C3 C4 1.373(5) . ? C3 H3 0.9300 . ? C4 C5 1.360(6) . ? C4 H4 0.9300 . ? C5 C6 1.372(6) . ? C5 C8 1.473(5) . ? C6 C7 1.373(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C12 1.362(5) . ? C8 C9 1.365(5) . ? C9 C10 1.369(5) . ? C9 H9 0.9300 . ? C10 C11 1.375(5) . ? C10 C13 1.469(5) . ? C11 N3 1.321(5) . ? C11 H11 0.9300 . ? C12 N3 1.333(5) . ? C12 H12 0.9300 . ? C13 C14 1.365(5) . ? C13 C19 1.375(5) . ? C14 C15 1.370(5) . ? C14 H14 0.9300 . ? C15 C16 1.374(5) . ? C15 H15 0.9300 . ? C16 C18 1.355(6) . ? C16 C17 1.493(6) . ? C17 O3 1.214(5) . ? C17 O4 1.233(5) . ? C17 Co1 2.463(4) 8_445 ? C18 C19 1.372(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.473(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 N2 1.320(5) . ? C21 N1 1.332(5) . ? C22 C23 1.315(6) . ? C22 N2 1.360(5) . ? C22 H22 0.9300 . ? C23 N1 1.357(6) . ? C23 H23 0.9300 . ? C24 N1 1.454(5) . ? C24 C25 1.511(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.302(9) . ? C25 C27 1.306(8) . ? C26 C27 1.355(8) 2_756 ? C26 H26 0.9300 . ? C27 C26 1.355(8) 2_756 ? C27 H27 0.9300 . ? Co1 O1 1.971(3) . ? Co1 N2 2.037(4) . ? Co1 N3 2.076(3) 3 ? Co1 O3 2.110(3) 8_546 ? Co1 O4 2.159(3) 8_546 ? Co1 C17 2.463(4) 8_546 ? N3 Co1 2.076(3) 3_445 ? O3 Co1 2.110(3) 8_445 ? O4 Co1 2.159(3) 8_445 ? O1W H1W 0.8199(12) . ? 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 C1 O1 123.4(4) . . ? O2 C1 C2 119.8(4) . . ? O1 C1 C2 116.8(4) . . ? C7 C2 C3 119.0(4) . . ? C7 C2 C1 121.3(4) . . ? C3 C2 C1 119.7(4) . . ? C2 C3 C4 120.3(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.9(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 118.6(4) . . ? C4 C5 C8 120.7(4) . . ? C6 C5 C8 120.7(4) . . ? C7 C6 C5 120.5(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C2 C7 C6 120.6(4) . . ? C2 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C12 C8 C9 118.5(3) . . ? C12 C8 C5 119.5(3) . . ? C9 C8 C5 122.1(3) . . ? C8 C9 C10 120.6(4) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 116.4(3) . . ? C9 C10 C13 123.5(3) . . ? C11 C10 C13 120.1(3) . . ? N3 C11 C10 124.3(3) . . ? N3 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? N3 C12 C8 122.5(3) . . ? N3 C12 H12 118.7 . . ? C8 C12 H12 118.7 . . ? C14 C13 C19 118.6(3) . . ? C14 C13 C10 121.7(3) . . ? C19 C13 C10 119.7(3) . . ? C13 C14 C15 121.5(4) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 119.6(4) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C18 C16 C15 119.2(4) . . ? C18 C16 C17 120.0(4) . . ? C15 C16 C17 120.7(4) . . ? O3 C17 O4 119.9(4) . . ? O3 C17 C16 121.4(4) . . ? O4 C17 C16 118.7(4) . . ? O3 C17 Co1 58.9(2) . 8_445 ? O4 C17 Co1 61.2(2) . 8_445 ? C16 C17 Co1 178.0(3) . 8_445 ? C16 C18 C19 121.3(4) . . ? C16 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C13 119.8(4) . . ? C18 C19 H19 120.1 . . ? C13 C19 H19 120.1 . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 N1 110.4(4) . . ? N2 C21 C20 126.0(4) . . ? N1 C21 C20 123.5(4) . . ? C23 C22 N2 111.0(4) . . ? C23 C22 H22 124.5 . . ? N2 C22 H22 124.5 . . ? C22 C23 N1 106.1(4) . . ? C22 C23 H23 127.0 . . ? N1 C23 H23 127.0 . . ? N1 C24 C25 110.8(4) . . ? N1 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? N1 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C26 C25 C27 115.8(5) . . ? C26 C25 C24 122.9(5) . . ? C27 C25 C24 121.3(6) . . ? C25 C26 C27 121.9(7) . 2_756 ? C25 C26 H26 119.0 . . ? C27 C26 H26 119.0 2_756 . ? C25 C27 C26 122.2(7) . 2_756 ? C25 C27 H27 118.9 . . ? C26 C27 H27 118.9 2_756 . ? O1 Co1 N2 104.93(13) . . ? O1 Co1 N3 103.37(13) . 3 ? N2 Co1 N3 94.02(12) . 3 ? O1 Co1 O3 148.59(15) . 8_546 ? N2 Co1 O3 99.47(14) . 8_546 ? N3 Co1 O3 94.22(13) 3 8_546 ? O1 Co1 O4 94.62(13) . 8_546 ? N2 Co1 O4 105.49(14) . 8_546 ? N3 Co1 O4 149.09(14) 3 8_546 ? O3 Co1 O4 59.51(13) 8_546 8_546 ? O1 Co1 C17 122.27(15) . 8_546 ? N2 Co1 C17 105.65(14) . 8_546 ? N3 Co1 C17 121.75(15) 3 8_546 ? O3 Co1 C17 29.52(13) 8_546 8_546 ? O4 Co1 C17 30.03(13) 8_546 8_546 ? C21 N1 C23 107.7(4) . . ? C21 N1 C24 126.0(4) . . ? C23 N1 C24 125.5(4) . . ? C21 N2 C22 104.8(4) . . ? C21 N2 Co1 131.9(3) . . ? C22 N2 Co1 122.7(3) . . ? C11 N3 C12 117.6(3) . . ? C11 N3 Co1 122.0(2) . 3_445 ? C12 N3 Co1 120.4(3) . 3_445 ? C1 O1 Co1 104.3(3) . . ? C17 O3 Co1 91.6(3) . 8_445 ? C17 O4 Co1 88.8(3) . 8_445 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.479 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 932484' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H20 Cu N3 O4' _chemical_formula_sum 'C27 H20 Cu N3 O4' _chemical_formula_weight 514.00 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.3079(15) _cell_length_b 10.1909(8) _cell_length_c 21.8461(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.201(2) _cell_angle_gamma 90.00 _cell_volume 4520.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1532 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 22.73 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8088 _exptl_absorpt_correction_T_max 0.9328 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11447 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3991 _reflns_number_gt 2765 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+8.8183P] 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 3991 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1494 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.004 _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 C1 C 0.6354(2) 0.3878(5) 1.2608(2) 0.0341(11) Uani 1 1 d . . . C2 C 0.6186(2) 0.4468(4) 1.1997(2) 0.0327(10) Uani 1 1 d . . . C3 C 0.6662(2) 0.5126(5) 1.1677(2) 0.0359(11) Uani 1 1 d . . . H3 H 0.7093 0.5151 1.1830 0.043 Uiso 1 1 calc R . . C4 C 0.6504(2) 0.5751(5) 1.1128(2) 0.0359(11) Uani 1 1 d . . . H4 H 0.6828 0.6203 1.0919 0.043 Uiso 1 1 calc R . . C5 C 0.5863(2) 0.5704(4) 1.08905(19) 0.0284(10) Uani 1 1 d . . . C6 C 0.5391(2) 0.5018(5) 1.1212(2) 0.0360(11) Uani 1 1 d . . . H6 H 0.4962 0.4966 1.1055 0.043 Uiso 1 1 calc R . . C7 C 0.5547(2) 0.4412(5) 1.1761(2) 0.0398(12) Uani 1 1 d . . . H7 H 0.5224 0.3966 1.1973 0.048 Uiso 1 1 calc R . . C8 C 0.5691(2) 0.6392(4) 1.03082(19) 0.0289(10) Uani 1 1 d . . . C9 C 0.6149(2) 0.6460(4) 0.98450(19) 0.0285(10) Uani 1 1 d . . . H9 H 0.6554 0.6053 0.9906 0.034 Uiso 1 1 calc R . . C10 C 0.5452(2) 0.7709(4) 0.9233(2) 0.0309(10) Uani 1 1 d . . . H10 H 0.5377 0.8179 0.8873 0.037 Uiso 1 1 calc R . . C11 C 0.4962(2) 0.7677(4) 0.9664(2) 0.0270(10) Uani 1 1 d . . . C12 C 0.5090(2) 0.6990(4) 1.02014(19) 0.0301(10) Uani 1 1 d . . . H12 H 0.4765 0.6931 1.0494 0.036 Uiso 1 1 calc R . . C13 C 0.4320(2) 0.8324(4) 0.95397(19) 0.0300(10) Uani 1 1 d . . . C14 C 0.4281(2) 0.9617(5) 0.9363(2) 0.0371(11) Uani 1 1 d . . . H14 H 0.4665 1.0104 0.9323 0.045 Uiso 1 1 calc R . . C15 C 0.3675(2) 1.0205(5) 0.9245(2) 0.0385(12) Uani 1 1 d . . . H15 H 0.3656 1.1091 0.9144 0.046 Uiso 1 1 calc R . . C16 C 0.3099(2) 0.9490(4) 0.92754(19) 0.0305(10) Uani 1 1 d . . . C17 C 0.3137(2) 0.8200(5) 0.9457(2) 0.0399(12) Uani 1 1 d . . . H17 H 0.2754 0.7707 0.9486 0.048 Uiso 1 1 calc R . . C18 C 0.3735(2) 0.7630(5) 0.9595(2) 0.0411(12) Uani 1 1 d . . . H18 H 0.3749 0.6764 0.9727 0.049 Uiso 1 1 calc R . . C19 C 0.2437(2) 1.0093(5) 0.9109(2) 0.0353(11) Uani 1 1 d . . . C20 C 0.6716(2) 0.9862(5) 0.9001(2) 0.0401(12) Uani 1 1 d . . . H20 H 0.6765 0.9594 0.9406 0.048 Uiso 1 1 calc R . . C21 C 0.6647(2) 1.1110(6) 0.8815(3) 0.0495(14) Uani 1 1 d . . . H21 H 0.6640 1.1853 0.9062 0.059 Uiso 1 1 calc R . . C22 C 0.6622(2) 0.9793(4) 0.8020(2) 0.0349(11) Uani 1 1 d . . . C23 C 0.6608(3) 0.9361(6) 0.7374(2) 0.0599(16) Uani 1 1 d . . . H23A H 0.6871 0.8584 0.7334 0.090 Uiso 1 1 calc R . . H23B H 0.6782 1.0043 0.7121 0.090 Uiso 1 1 calc R . . H23C H 0.6162 0.9175 0.7247 0.090 Uiso 1 1 calc R . . C24 C 0.6407(3) 1.2173(5) 0.7795(3) 0.0627(17) Uani 1 1 d . . . H24A H 0.6651 1.2121 0.7418 0.075 Uiso 1 1 calc R . . H24B H 0.6526 1.2988 0.7998 0.075 Uiso 1 1 calc R . . C25 C 0.5674(3) 1.2173(5) 0.7644(3) 0.0592(17) Uani 1 1 d . . . C26 C 0.5224(4) 1.2163(12) 0.8064(4) 0.157(6) Uani 1 1 d . . . H26 H 0.5358 1.2147 0.8473 0.188 Uiso 1 1 calc R . . C27 C 0.5445(4) 1.2173(12) 0.7075(4) 0.145(5) Uani 1 1 d . . . H27 H 0.5742 1.2179 0.6757 0.174 Uiso 1 1 calc R . . Cu1 Cu 0.66529(2) 0.69444(6) 0.86020(2) 0.0309(2) Uani 1 1 d . . . N1 N 0.60336(16) 0.7084(3) 0.93156(16) 0.0290(8) Uani 1 1 d . . . N2 N 0.67055(17) 0.9046(4) 0.85054(16) 0.0308(9) Uani 1 1 d . . . N3 N 0.65885(19) 1.1069(4) 0.8190(2) 0.0435(10) Uani 1 1 d . . . O1 O 0.59134(15) 0.3431(4) 1.29429(14) 0.0430(9) Uani 1 1 d . . . O2 O 0.69483(15) 0.3807(4) 1.27900(14) 0.0452(9) Uani 1 1 d . . . O3 O 0.19484(16) 0.9384(4) 0.90491(18) 0.0521(10) Uani 1 1 d . . . O4 O 0.24356(14) 1.1341(3) 0.90440(14) 0.0376(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(2) 0.042(3) 0.030(3) 0.005(2) -0.004(2) 0.002(2) C2 0.031(2) 0.039(3) 0.028(2) 0.003(2) -0.0016(19) 0.000(2) C3 0.022(2) 0.050(3) 0.036(3) 0.011(2) -0.003(2) 0.003(2) C4 0.026(2) 0.048(3) 0.033(3) 0.010(2) 0.0037(19) 0.000(2) C5 0.025(2) 0.032(3) 0.028(2) 0.0001(19) -0.0026(18) 0.0038(19) C6 0.026(2) 0.044(3) 0.038(3) 0.010(2) -0.011(2) -0.004(2) C7 0.025(2) 0.054(3) 0.040(3) 0.018(2) -0.007(2) -0.008(2) C8 0.026(2) 0.031(2) 0.029(2) 0.0019(19) -0.0021(19) 0.0052(19) C9 0.027(2) 0.032(2) 0.027(2) 0.0045(19) -0.0037(18) 0.0065(19) C10 0.033(2) 0.031(3) 0.028(2) 0.0047(19) -0.0034(19) 0.006(2) C11 0.026(2) 0.025(2) 0.030(2) -0.0028(18) -0.0005(18) 0.0048(18) C12 0.026(2) 0.036(3) 0.028(2) 0.002(2) 0.0006(18) 0.004(2) C13 0.027(2) 0.039(3) 0.024(2) 0.0000(19) -0.0023(18) 0.009(2) C14 0.025(2) 0.036(3) 0.050(3) 0.003(2) -0.007(2) 0.000(2) C15 0.035(3) 0.030(3) 0.050(3) 0.001(2) -0.009(2) 0.010(2) C16 0.024(2) 0.040(3) 0.028(2) -0.006(2) 0.0030(18) 0.008(2) C17 0.025(2) 0.043(3) 0.052(3) 0.007(2) 0.002(2) 0.008(2) C18 0.033(3) 0.036(3) 0.055(3) 0.009(2) 0.005(2) 0.010(2) C19 0.034(3) 0.041(3) 0.031(3) -0.004(2) -0.001(2) 0.013(2) C20 0.039(3) 0.047(3) 0.034(3) -0.007(2) -0.002(2) -0.003(2) C21 0.040(3) 0.050(4) 0.058(4) -0.017(3) -0.006(3) 0.000(3) C22 0.032(2) 0.032(3) 0.040(3) 0.003(2) -0.008(2) -0.005(2) C23 0.085(4) 0.059(4) 0.036(3) 0.010(3) -0.005(3) -0.019(3) C24 0.059(4) 0.036(3) 0.092(5) 0.017(3) -0.026(3) -0.006(3) C25 0.061(4) 0.026(3) 0.089(5) 0.006(3) -0.028(4) 0.000(3) C26 0.066(5) 0.298(15) 0.105(7) -0.128(8) -0.046(5) 0.077(7) C27 0.062(5) 0.268(13) 0.103(7) 0.122(8) -0.022(5) -0.063(6) Cu1 0.0245(3) 0.0420(4) 0.0262(3) 0.0010(2) -0.0011(2) 0.0084(2) N1 0.0239(18) 0.035(2) 0.028(2) 0.0040(16) -0.0019(15) 0.0069(16) N2 0.032(2) 0.033(2) 0.028(2) 0.0039(17) -0.0011(16) -0.0053(16) N3 0.039(2) 0.032(2) 0.060(3) 0.006(2) -0.011(2) -0.0054(19) O1 0.0322(18) 0.065(2) 0.0316(18) 0.0173(16) -0.0004(15) -0.0007(16) O2 0.0331(18) 0.071(3) 0.0312(18) 0.0126(17) -0.0057(15) -0.0038(17) O3 0.0287(19) 0.048(2) 0.080(3) -0.005(2) -0.0067(18) 0.0085(17) O4 0.0316(17) 0.040(2) 0.0409(19) -0.0005(15) -0.0095(14) 0.0116(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.254(5) . ? C1 O2 1.265(5) . ? C1 C2 1.497(6) . ? C1 Cu1 2.394(4) 6_566 ? C2 C3 1.379(6) . ? C2 C7 1.387(6) . ? C3 C4 1.389(6) . ? C3 H3 0.9300 . ? C4 C5 1.394(6) . ? C4 H4 0.9300 . ? C5 C6 1.389(6) . ? C5 C8 1.487(6) . ? C6 C7 1.379(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C12 1.380(6) . ? C8 C9 1.390(6) . ? C9 N1 1.336(5) . ? C9 H9 0.9300 . ? C10 N1 1.351(5) . ? C10 C11 1.384(6) . ? C10 H10 0.9300 . ? C11 C12 1.387(6) . ? C11 C13 1.480(6) . ? C12 H12 0.9300 . ? C13 C14 1.375(6) . ? C13 C18 1.390(6) . ? C14 C15 1.388(6) . ? C14 H14 0.9300 . ? C15 C16 1.380(6) . ? C15 H15 0.9300 . ? C16 C17 1.375(6) . ? C16 C19 1.517(6) . ? C17 C18 1.373(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 O3 1.232(6) . ? C19 O4 1.280(6) . ? C20 C21 1.341(7) . ? C20 N2 1.365(6) . ? C20 H20 0.9300 . ? C21 N3 1.370(7) . ? C21 H21 0.9300 . ? C22 N2 1.314(6) . ? C22 N3 1.354(6) . ? C22 C23 1.479(7) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N3 1.460(6) . ? C24 C25 1.519(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.309(11) . ? C25 C27 1.317(10) . ? C26 C27 1.385(10) 2_656 ? C26 H26 0.9300 . ? C27 C26 1.385(10) 2_656 ? C27 H27 0.9300 . ? Cu1 O4 1.942(3) 3_545 ? Cu1 N1 2.028(3) . ? Cu1 O2 2.034(3) 6_565 ? Cu1 O1 2.094(3) 6_565 ? Cu1 N2 2.155(4) . ? Cu1 C1 2.394(4) 6_565 ? O1 Cu1 2.094(3) 6_566 ? O2 Cu1 2.034(3) 6_566 ? O4 Cu1 1.942(3) 3_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 O1 C1 O2 118.9(4) . . ? O1 C1 C2 121.0(4) . . ? O2 C1 C2 120.1(4) . . ? O1 C1 Cu1 60.9(2) . 6_566 ? O2 C1 Cu1 58.2(2) . 6_566 ? C2 C1 Cu1 176.6(4) . 6_566 ? C3 C2 C7 119.5(4) . . ? C3 C2 C1 119.8(4) . . ? C7 C2 C1 120.6(4) . . ? C2 C3 C4 120.5(4) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 120.2(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 118.6(4) . . ? C6 C5 C8 121.2(4) . . ? C4 C5 C8 120.2(4) . . ? C7 C6 C5 121.0(4) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C2 120.1(4) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C12 C8 C9 117.2(4) . . ? C12 C8 C5 122.9(4) . . ? C9 C8 C5 119.9(4) . . ? N1 C9 C8 123.2(4) . . ? N1 C9 H9 118.4 . . ? C8 C9 H9 118.4 . . ? N1 C10 C11 122.5(4) . . ? N1 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C10 C11 C12 117.6(4) . . ? C10 C11 C13 120.5(4) . . ? C12 C11 C13 121.9(4) . . ? C8 C12 C11 121.0(4) . . ? C8 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C18 117.8(4) . . ? C14 C13 C11 121.6(4) . . ? C18 C13 C11 120.6(4) . . ? C13 C14 C15 120.8(4) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 120.7(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 118.5(4) . . ? C17 C16 C19 120.0(4) . . ? C15 C16 C19 121.5(4) . . ? C18 C17 C16 120.8(5) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C13 121.3(5) . . ? C17 C18 H18 119.3 . . ? C13 C18 H18 119.4 . . ? O3 C19 O4 124.8(4) . . ? O3 C19 C16 119.8(4) . . ? O4 C19 C16 115.4(4) . . ? C21 C20 N2 109.8(5) . . ? C21 C20 H20 125.1 . . ? N2 C20 H20 125.1 . . ? C20 C21 N3 106.2(4) . . ? C20 C21 H21 126.9 . . ? N3 C21 H21 126.9 . . ? N2 C22 N3 110.0(4) . . ? N2 C22 C23 126.7(4) . . ? N3 C22 C23 123.2(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 C25 111.2(4) . . ? N3 C24 H24A 109.4 . . ? C25 C24 H24A 109.4 . . ? N3 C24 H24B 109.4 . . ? C25 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C26 C25 C27 115.0(7) . . ? C26 C25 C24 123.0(6) . . ? C27 C25 C24 122.0(7) . . ? C25 C26 C27 122.9(8) . 2_656 ? C25 C26 H26 118.6 . . ? C27 C26 H26 118.6 2_656 . ? C25 C27 C26 122.1(8) . 2_656 ? C25 C27 H27 119.0 . . ? C26 C27 H27 119.0 2_656 . ? O4 Cu1 N1 98.87(13) 3_545 . ? O4 Cu1 O2 93.51(13) 3_545 6_565 ? N1 Cu1 O2 153.59(14) . 6_565 ? O4 Cu1 O1 148.42(14) 3_545 6_565 ? N1 Cu1 O1 95.39(13) . 6_565 ? O2 Cu1 O1 63.39(12) 6_565 6_565 ? O4 Cu1 N2 108.74(14) 3_545 . ? N1 Cu1 N2 92.21(14) . . ? O2 Cu1 N2 105.81(14) 6_565 . ? O1 Cu1 N2 98.65(14) 6_565 . ? O4 Cu1 C1 121.97(15) 3_545 6_565 ? N1 Cu1 C1 124.91(15) . 6_565 ? O2 Cu1 C1 31.89(13) 6_565 6_565 ? O1 Cu1 C1 31.55(13) 6_565 6_565 ? N2 Cu1 C1 105.73(15) . 6_565 ? C9 N1 C10 118.5(4) . . ? C9 N1 Cu1 122.1(3) . . ? C10 N1 Cu1 119.0(3) . . ? C22 N2 C20 106.6(4) . . ? C22 N2 Cu1 130.5(3) . . ? C20 N2 Cu1 121.9(3) . . ? C22 N3 C21 107.4(4) . . ? C22 N3 C24 126.2(5) . . ? C21 N3 C24 125.6(5) . . ? C1 O1 Cu1 87.6(3) . 6_566 ? C1 O2 Cu1 89.9(3) . 6_566 ? C19 O4 Cu1 111.7(3) . 3_455 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.288 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 932487' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H20 N3 Ni O4' _chemical_formula_sum 'C27 H20 N3 Ni O4' _chemical_formula_weight 509.17 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.249(10) _cell_length_b 10.011(5) _cell_length_c 22.164(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.228(12) _cell_angle_gamma 90.00 _cell_volume 4492(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1153 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 19.66 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2104 _exptl_absorpt_coefficient_mu 0.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7922 _exptl_absorpt_correction_T_max 0.8914 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 14010 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.1142 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.35 _reflns_number_total 5483 _reflns_number_gt 2973 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^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 5483 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1267 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 C1 C 0.11257(17) 0.6389(3) 0.48576(17) 0.0289(9) Uani 1 1 d . . . H1 H 0.1530 0.5963 0.4917 0.035 Uiso 1 1 calc R . . C2 C 0.06743(16) 0.6336(3) 0.53186(17) 0.0260(8) Uani 1 1 d . . . C3 C 0.00636(16) 0.6935(3) 0.52069(17) 0.0297(9) Uani 1 1 d . . . H3 H -0.0264 0.6874 0.5493 0.036 Uiso 1 1 calc R . . C4 C -0.00601(16) 0.7621(3) 0.46736(17) 0.0263(8) Uani 1 1 d . . . C5 C 0.04297(16) 0.7633(4) 0.42507(18) 0.0311(9) Uani 1 1 d . . . H5 H 0.0352 0.8091 0.3891 0.037 Uiso 1 1 calc R . . C6 C 0.08529(17) 0.5682(4) 0.58999(17) 0.0287(9) Uani 1 1 d . . . C7 C 0.15041(17) 0.5732(4) 0.61227(18) 0.0340(10) Uani 1 1 d . . . H7 H 0.1825 0.6167 0.5902 0.041 Uiso 1 1 calc R . . C8 C 0.16744(17) 0.5143(4) 0.66667(18) 0.0337(9) Uani 1 1 d . . . H8 H 0.2112 0.5166 0.6804 0.040 Uiso 1 1 calc R . . C9 C 0.12050(17) 0.4518(4) 0.70106(17) 0.0307(9) Uani 1 1 d . . . C10 C 0.05557(18) 0.4457(4) 0.67854(18) 0.0397(10) Uani 1 1 d . . . H10 H 0.0235 0.4018 0.7005 0.048 Uiso 1 1 calc R . . C11 C 0.03864(17) 0.5038(4) 0.62421(17) 0.0336(9) Uani 1 1 d . . . H11 H -0.0049 0.4999 0.6102 0.040 Uiso 1 1 calc R . . C12 C 0.13875(18) 0.3953(4) 0.76132(18) 0.0308(9) Uani 1 1 d . . . C13 C -0.06943(16) 0.8331(4) 0.45472(17) 0.0288(9) Uani 1 1 d . . . C14 C -0.06932(18) 0.9646(4) 0.43833(19) 0.0396(11) Uani 1 1 d . . . H14 H -0.0294 1.0099 0.4354 0.048 Uiso 1 1 calc R . . C15 C -0.12823(18) 1.0316(4) 0.42598(19) 0.0388(10) Uani 1 1 d . . . H15 H -0.1276 1.1220 0.4165 0.047 Uiso 1 1 calc R . . C16 C -0.18761(17) 0.9646(4) 0.42775(17) 0.0298(9) Uani 1 1 d . . . C17 C -0.18762(17) 0.8333(4) 0.44355(19) 0.0395(11) Uani 1 1 d . . . H17 H -0.2274 0.7871 0.4444 0.047 Uiso 1 1 calc R . . C18 C -0.12967(18) 0.7674(4) 0.4583(2) 0.0432(11) Uani 1 1 d . . . H18 H -0.1309 0.6786 0.4706 0.052 Uiso 1 1 calc R . . C19 C -0.25018(18) 1.0384(4) 0.40952(17) 0.0333(9) Uani 1 1 d . . . C20 C 0.16999(18) 0.9746(4) 0.4006(2) 0.0416(11) Uani 1 1 d . . . H20 H 0.1757 0.9472 0.4404 0.050 Uiso 1 1 calc R . . C21 C 0.16358(18) 1.1016(4) 0.3825(2) 0.0452(12) Uani 1 1 d . . . H21 H 0.1636 1.1773 0.4067 0.054 Uiso 1 1 calc R . . C22 C 0.15920(17) 0.9688(4) 0.30372(18) 0.0337(9) Uani 1 1 d . . . C23 C 0.1561(2) 0.9262(5) 0.2393(2) 0.0609(14) Uani 1 1 d . . . H23A H 0.1815 0.8460 0.2346 0.091 Uiso 1 1 calc R . . H23B H 0.1739 0.9955 0.2145 0.091 Uiso 1 1 calc R . . H23C H 0.1110 0.9097 0.2274 0.091 Uiso 1 1 calc R . . C24 C 0.1406(2) 1.2124(4) 0.2821(2) 0.0571(14) Uani 1 1 d . . . H24A H 0.1664 1.2083 0.2457 0.068 Uiso 1 1 calc R . . H24B H 0.1519 1.2945 0.3031 0.068 Uiso 1 1 calc R . . C25 C 0.0673(2) 1.2130(4) 0.2651(2) 0.0514(13) Uani 1 1 d . . . C26 C 0.0207(3) 1.2112(7) 0.3073(3) 0.119(3) Uani 1 1 d . . . H26 H 0.0336 1.2094 0.3478 0.143 Uiso 1 1 calc R . . C27 C 0.0461(3) 1.2119(8) 0.2080(3) 0.125(3) Uani 1 1 d . . . H27 H 0.0769 1.2116 0.1774 0.151 Uiso 1 1 calc R . . N1 N 0.10144(13) 0.7015(3) 0.43322(14) 0.0287(7) Uani 1 1 d . . . N2 N 0.16680(14) 0.8898(3) 0.35113(14) 0.0321(8) Uani 1 1 d . . . N3 N 0.15705(15) 1.0971(3) 0.32100(17) 0.0406(9) Uani 1 1 d . . . Ni1 Ni 0.16548(2) 0.68672(5) 0.36198(2) 0.02840(15) Uani 1 1 d . . . O1 O 0.09449(12) 0.3611(3) 0.79750(12) 0.0401(7) Uani 1 1 d . . . O2 O 0.19857(12) 0.3803(3) 0.77618(12) 0.0392(7) Uani 1 1 d . . . O3 O -0.30149(12) 0.9746(3) 0.39542(13) 0.0440(8) Uani 1 1 d . . . O4 O -0.24803(11) 1.1646(3) 0.40823(12) 0.0381(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 C1 0.0239(19) 0.034(2) 0.028(2) 0.0011(18) -0.0050(17) 0.0069(16) C2 0.0220(18) 0.027(2) 0.029(2) 0.0000(17) -0.0025(17) 0.0001(15) C3 0.0250(19) 0.034(2) 0.030(2) 0.0014(19) 0.0001(16) 0.0020(17) C4 0.0219(18) 0.0251(19) 0.032(2) 0.0002(17) 0.0000(17) 0.0012(15) C5 0.027(2) 0.033(2) 0.033(2) 0.0035(18) -0.0023(18) 0.0065(16) C6 0.028(2) 0.032(2) 0.026(2) 0.0046(18) 0.0018(17) 0.0038(17) C7 0.0243(19) 0.042(2) 0.036(2) 0.011(2) 0.0038(18) -0.0018(17) C8 0.0211(19) 0.046(2) 0.034(2) 0.008(2) -0.0038(18) 0.0014(17) C9 0.0244(19) 0.038(2) 0.030(2) 0.0102(19) -0.0012(17) -0.0006(17) C10 0.029(2) 0.057(3) 0.033(3) 0.012(2) -0.0049(19) -0.0108(19) C11 0.0211(18) 0.047(2) 0.033(2) 0.011(2) -0.0051(17) -0.0041(17) C12 0.028(2) 0.034(2) 0.031(2) 0.0028(18) -0.0057(19) 0.0000(17) C13 0.0257(19) 0.032(2) 0.028(2) -0.0013(18) -0.0027(16) 0.0069(16) C14 0.027(2) 0.036(2) 0.056(3) 0.001(2) -0.004(2) 0.0017(18) C15 0.032(2) 0.031(2) 0.054(3) 0.006(2) -0.006(2) 0.0059(18) C16 0.0237(19) 0.038(2) 0.028(2) -0.0040(18) -0.0044(17) 0.0079(17) C17 0.0200(18) 0.037(2) 0.062(3) 0.004(2) -0.0014(19) 0.0006(17) C18 0.032(2) 0.038(2) 0.060(3) 0.015(2) 0.000(2) 0.0068(19) C19 0.028(2) 0.042(3) 0.030(2) -0.001(2) 0.0016(18) 0.0103(19) C20 0.033(2) 0.057(3) 0.034(3) -0.006(2) -0.0019(19) 0.001(2) C21 0.038(2) 0.039(3) 0.058(3) -0.009(2) -0.002(2) 0.001(2) C22 0.033(2) 0.036(2) 0.031(2) 0.000(2) -0.0056(19) -0.0009(18) C23 0.088(4) 0.051(3) 0.043(3) 0.009(2) -0.009(3) -0.005(3) C24 0.051(3) 0.034(3) 0.085(4) 0.013(3) -0.018(3) -0.005(2) C25 0.051(3) 0.032(3) 0.070(4) 0.007(2) -0.023(3) -0.003(2) C26 0.060(4) 0.219(8) 0.076(5) -0.084(5) -0.030(3) 0.051(4) C27 0.051(4) 0.229(9) 0.095(5) 0.097(6) -0.025(3) -0.053(4) N1 0.0232(15) 0.0321(18) 0.0307(19) 0.0020(15) -0.0048(14) 0.0058(13) N2 0.0293(17) 0.0384(19) 0.029(2) 0.0047(16) 0.0002(15) -0.0026(15) N3 0.0364(19) 0.033(2) 0.052(3) 0.0006(18) -0.0096(18) -0.0013(15) Ni1 0.0216(2) 0.0358(3) 0.0277(3) -0.0015(3) -0.00160(19) 0.0046(2) O1 0.0273(14) 0.0601(19) 0.0330(17) 0.0127(14) 0.0035(13) -0.0011(13) O2 0.0261(14) 0.0552(18) 0.0360(17) 0.0124(14) -0.0030(13) -0.0051(13) O3 0.0253(14) 0.0494(18) 0.057(2) -0.0077(15) -0.0051(14) 0.0056(13) O4 0.0292(14) 0.0384(17) 0.0463(18) 0.0008(14) -0.0069(13) 0.0106(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.337(4) . ? C1 C2 1.387(5) . ? C1 H1 0.9300 . ? C2 C3 1.392(4) . ? C2 C6 1.483(5) . ? C3 C4 1.385(5) . ? C3 H3 0.9300 . ? C4 C5 1.379(5) . ? C4 C13 1.489(4) . ? C5 N1 1.344(4) . ? C5 H5 0.9300 . ? C6 C7 1.399(5) . ? C6 C11 1.383(5) . ? C7 C8 1.380(5) . ? C7 H7 0.9300 . ? C8 C9 1.381(5) . ? C8 H8 0.9300 . ? C9 C10 1.398(5) . ? C9 C12 1.490(5) . ? C10 C11 1.374(5) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 O2 1.257(4) . ? C12 O1 1.263(4) . ? C12 Ni1 2.427(4) 6_566 ? C13 C14 1.366(5) . ? C13 C18 1.390(5) . ? C14 C15 1.391(5) . ? C14 H14 0.9300 . ? C15 C16 1.378(5) . ? C15 H15 0.9300 . ? C16 C17 1.360(5) . ? C16 C19 1.514(5) . ? C17 C18 1.380(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 O3 1.253(4) . ? C19 O4 1.264(4) . ? C19 Ni1 2.481(4) 3_455 ? C20 C21 1.339(6) . ? C20 N2 1.386(5) . ? C20 H20 0.9300 . ? C21 N3 1.366(5) . ? C21 H21 0.9300 . ? C22 N2 1.321(5) . ? C22 N3 1.342(5) . ? C22 C23 1.490(6) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N3 1.475(5) . ? C24 C25 1.523(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C27 1.328(7) . ? C25 C26 1.342(7) . ? C26 C27 1.389(7) 2 ? C26 H26 0.9300 . ? C27 C26 1.389(7) 2 ? C27 H27 0.9300 . ? N1 Ni1 2.070(3) . ? N2 Ni1 2.047(3) . ? Ni1 O4 2.022(2) 3_545 ? Ni1 O1 2.061(3) 6_565 ? Ni1 O2 2.138(3) 6_565 ? Ni1 O3 2.342(3) 3_545 ? Ni1 C12 2.427(4) 6_565 ? Ni1 C19 2.481(4) 3_545 ? O1 Ni1 2.061(3) 6_566 ? O2 Ni1 2.138(3) 6_566 ? O3 Ni1 2.342(3) 3_455 ? O4 Ni1 2.022(2) 3_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 N1 C1 C2 123.9(3) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 116.7(3) . . ? C1 C2 C6 120.3(3) . . ? C3 C2 C6 123.0(3) . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 117.7(3) . . ? C3 C4 C13 122.5(3) . . ? C5 C4 C13 119.9(3) . . ? N1 C5 C4 123.3(3) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C7 C6 C11 118.2(3) . . ? C7 C6 C2 120.1(3) . . ? C11 C6 C2 121.7(3) . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.9(3) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 118.4(3) . . ? C10 C9 C12 121.1(3) . . ? C8 C9 C12 120.4(3) . . ? C9 C10 C11 120.6(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C6 121.2(3) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? O2 C12 O1 119.6(3) . . ? O2 C12 C9 119.9(3) . . ? O1 C12 C9 120.4(3) . . ? O2 C12 Ni1 61.61(19) . 6_566 ? O1 C12 Ni1 58.13(19) . 6_566 ? C9 C12 Ni1 176.9(3) . 6_566 ? C14 C13 C18 118.6(3) . . ? C14 C13 C4 120.3(3) . . ? C18 C13 C4 121.2(3) . . ? C13 C14 C15 120.7(3) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 120.3(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 118.9(3) . . ? C17 C16 C19 122.4(3) . . ? C15 C16 C19 118.7(3) . . ? C16 C17 C18 121.2(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C13 C18 C17 120.2(4) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? O3 C19 O4 122.2(3) . . ? O3 C19 C16 120.1(4) . . ? O4 C19 C16 117.7(3) . . ? O3 C19 Ni1 68.9(2) . 3_455 ? O4 C19 Ni1 54.28(17) . 3_455 ? C16 C19 Ni1 165.9(3) . 3_455 ? C21 C20 N2 110.0(4) . . ? C21 C20 H20 125.0 . . ? N2 C20 H20 125.0 . . ? C20 C21 N3 105.9(4) . . ? C20 C21 H21 127.0 . . ? N3 C21 H21 127.0 . . ? N2 C22 N3 110.5(4) . . ? N2 C22 C23 126.3(4) . . ? N3 C22 C23 123.1(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N3 C24 C25 110.7(3) . . ? N3 C24 H24A 109.5 . . ? C25 C24 H24A 109.5 . . ? N3 C24 H24B 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? C27 C25 C26 116.5(5) . . ? C27 C25 C24 121.9(5) . . ? C26 C25 C24 121.6(5) . . ? C25 C26 C27 121.7(6) . 2 ? C25 C26 H26 119.1 . . ? C27 C26 H26 119.1 2 . ? C25 C27 C26 121.7(6) . 2 ? C25 C27 H27 119.1 . . ? C26 C27 H27 119.1 2 . ? C1 N1 C5 117.7(3) . . ? C1 N1 Ni1 122.3(2) . . ? C5 N1 Ni1 119.6(2) . . ? C22 N2 C20 105.4(3) . . ? C22 N2 Ni1 133.3(3) . . ? C20 N2 Ni1 121.0(3) . . ? C22 N3 C21 108.2(4) . . ? C22 N3 C24 126.2(4) . . ? C21 N3 C24 125.0(4) . . ? O4 Ni1 N2 98.92(11) 3_545 . ? O4 Ni1 O1 155.41(11) 3_545 6_565 ? N2 Ni1 O1 99.18(12) . 6_565 ? O4 Ni1 N1 99.85(12) 3_545 . ? N2 Ni1 N1 91.64(12) . . ? O1 Ni1 N1 96.12(11) 6_565 . ? O4 Ni1 O2 97.58(11) 3_545 6_565 ? N2 Ni1 O2 101.65(12) . 6_565 ? O1 Ni1 O2 62.46(10) 6_565 6_565 ? N1 Ni1 O2 156.13(11) . 6_565 ? O4 Ni1 O3 60.12(10) 3_545 3_545 ? N2 Ni1 O3 158.92(11) . 3_545 ? O1 Ni1 O3 101.50(10) 6_565 3_545 ? N1 Ni1 O3 90.16(11) . 3_545 ? O2 Ni1 O3 84.50(10) 6_565 3_545 ? O4 Ni1 C12 127.03(12) 3_545 6_565 ? N2 Ni1 C12 103.35(13) . 6_565 ? O1 Ni1 C12 31.34(10) 6_565 6_565 ? N1 Ni1 C12 126.47(12) . 6_565 ? O2 Ni1 C12 31.16(10) 6_565 6_565 ? O3 Ni1 C12 92.34(12) 3_545 6_565 ? O4 Ni1 C19 30.49(11) 3_545 3_545 ? N2 Ni1 C19 129.31(13) . 3_545 ? O1 Ni1 C19 128.25(13) 6_565 3_545 ? N1 Ni1 C19 98.95(12) . 3_545 ? O2 Ni1 C19 87.93(12) 6_565 3_545 ? O3 Ni1 C19 29.95(10) 3_545 3_545 ? C12 Ni1 C19 109.02(13) 6_565 3_545 ? C12 O1 Ni1 90.5(2) . 6_566 ? C12 O2 Ni1 87.2(2) . 6_566 ? C19 O3 Ni1 81.2(2) . 3_455 ? C19 O4 Ni1 95.2(2) . 3_455 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.472 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 932489' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C56 H42 Co2 N6 O11), 5(H2 O)' _chemical_formula_sum 'C112 H94 Co4 N12 O27' _chemical_formula_weight 2275.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' 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' _cell_length_a 27.381(6) _cell_length_b 11.289(2) _cell_length_c 18.020(4) _cell_angle_alpha 90.00 _cell_angle_beta 117.075(4) _cell_angle_gamma 90.00 _cell_volume 4959.6(17) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1579 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 20.80 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2348 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7253 _exptl_absorpt_correction_T_max 0.9496 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12957 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7812 _reflns_number_gt 5704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+4.5082P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 7812 _refine_ls_number_parameters 732 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.995 _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 C1 C 0.1396(3) -0.0678(8) 1.3171(5) 0.0277(18) Uani 1 1 d . . . H1 H 0.1481 -0.1219 1.3602 0.033 Uiso 1 1 calc R . . C2 C 0.0823(3) -0.0099(7) 1.1823(5) 0.0309(19) Uani 1 1 d . . . H2 H 0.0515 -0.0244 1.1320 0.037 Uiso 1 1 calc R . . C3 C 0.1130(3) 0.0928(7) 1.1893(4) 0.0259(18) Uani 1 1 d . . . C4 C 0.1593(3) 0.1093(8) 1.2664(5) 0.0338(19) Uani 1 1 d . . . H4 H 0.1813 0.1757 1.2744 0.041 Uiso 1 1 calc R . . C5 C 0.1728(3) 0.0295(8) 1.3302(4) 0.0270(18) Uani 1 1 d . . . C6 C 0.2202(3) 0.0468(8) 1.4149(5) 0.0278(19) Uani 1 1 d . . . C7 C 0.2619(3) 0.1251(9) 1.4296(5) 0.041(2) Uani 1 1 d . . . H7 H 0.2608 0.1694 1.3853 0.050 Uiso 1 1 calc R . . C8 C 0.3053(3) 0.1406(8) 1.5071(5) 0.039(2) Uani 1 1 d . . . H8 H 0.3327 0.1945 1.5139 0.046 Uiso 1 1 calc R . . C9 C 0.3089(3) 0.0775(7) 1.5749(5) 0.0298(19) Uani 1 1 d . . . C10 C 0.2688(4) -0.0028(9) 1.5625(6) 0.052(3) Uani 1 1 d . . . H10 H 0.2708 -0.0478 1.6070 0.062 Uiso 1 1 calc R . . C11 C 0.2244(4) -0.0183(9) 1.4829(5) 0.056(3) Uani 1 1 d . . . H11 H 0.1973 -0.0733 1.4757 0.067 Uiso 1 1 calc R . . C12 C 0.3543(3) 0.1022(8) 1.6615(5) 0.034(2) Uani 1 1 d . . . C13 C 0.0964(3) 0.1757(7) 1.1196(5) 0.0265(18) Uani 1 1 d . . . C14 C 0.0996(3) 0.2979(8) 1.1336(5) 0.036(2) Uani 1 1 d . . . H14 H 0.1137 0.3262 1.1879 0.043 Uiso 1 1 calc R . . C15 C 0.0823(4) 0.3766(8) 1.0690(5) 0.038(2) Uani 1 1 d . . . H15 H 0.0847 0.4574 1.0803 0.046 Uiso 1 1 calc R . . C16 C 0.0615(3) 0.3390(7) 0.9883(5) 0.0272(18) Uani 1 1 d . . . C17 C 0.0582(3) 0.2179(8) 0.9727(5) 0.034(2) Uani 1 1 d . . . H17 H 0.0448 0.1905 0.9183 0.041 Uiso 1 1 calc R . . C18 C 0.0750(3) 0.1372(8) 1.0384(5) 0.036(2) Uani 1 1 d . . . H18 H 0.0716 0.0563 1.0272 0.044 Uiso 1 1 calc R . . C19 C 0.0396(3) 0.4251(8) 0.9168(4) 0.0298(19) Uani 1 1 d . . . C20 C 0.1312(3) 0.2685(8) 0.8274(5) 0.0317(18) Uani 1 1 d . . . H20 H 0.1392 0.3206 0.8714 0.038 Uiso 1 1 calc R . . C21 C 0.1670(3) 0.1761(7) 0.8420(4) 0.0241(17) Uani 1 1 d . . . C22 C 0.1537(3) 0.1019(8) 0.7733(4) 0.0307(19) Uani 1 1 d . . . H22 H 0.1762 0.0376 0.7784 0.037 Uiso 1 1 calc R . . C23 C 0.1081(3) 0.1220(8) 0.6980(4) 0.0314(19) Uani 1 1 d . . . C24 C 0.0757(3) 0.2145(8) 0.6934(5) 0.034(2) Uani 1 1 d . . . H24 H 0.0441 0.2267 0.6437 0.040 Uiso 1 1 calc R . . C25 C 0.0934(3) 0.0394(8) 0.6265(5) 0.0294(18) Uani 1 1 d . . . C26 C 0.0985(4) -0.0810(8) 0.6360(5) 0.043(2) Uani 1 1 d . . . H26 H 0.1117 -0.1137 0.6890 0.052 Uiso 1 1 calc R . . C27 C 0.0842(4) -0.1553(8) 0.5674(5) 0.041(2) Uani 1 1 d . . . H27 H 0.0877 -0.2369 0.5751 0.050 Uiso 1 1 calc R . . C28 C 0.0645(3) -0.1085(8) 0.4868(5) 0.032(2) Uani 1 1 d . . . C29 C 0.0596(4) 0.0125(8) 0.4777(6) 0.039(2) Uani 1 1 d . . . H29 H 0.0464 0.0452 0.4246 0.047 Uiso 1 1 calc R . . C30 C 0.0737(3) 0.0861(8) 0.5447(5) 0.033(2) Uani 1 1 d . . . H30 H 0.0704 0.1676 0.5367 0.040 Uiso 1 1 calc R . . C31 C 0.0480(3) -0.1878(8) 0.4124(5) 0.033(2) Uani 1 1 d . . . C32 C 0.2161(3) 0.1606(7) 0.9227(5) 0.0289(19) Uani 1 1 d . . . C33 C 0.2602(3) 0.0941(8) 0.9296(5) 0.037(2) Uani 1 1 d . . . H33 H 0.2596 0.0600 0.8822 0.045 Uiso 1 1 calc R . . C34 C 0.3050(3) 0.0776(9) 1.0058(5) 0.041(2) Uani 1 1 d . . . H34 H 0.3338 0.0306 1.0090 0.050 Uiso 1 1 calc R . . C35 C 0.3086(3) 0.1286(8) 1.0776(5) 0.034(2) Uani 1 1 d . . . C36 C 0.2648(4) 0.1946(9) 1.0716(5) 0.049(3) Uani 1 1 d . . . H36 H 0.2657 0.2291 1.1190 0.058 Uiso 1 1 calc R . . C37 C 0.2193(3) 0.2100(8) 0.9951(5) 0.044(2) Uani 1 1 d . . . H37 H 0.1900 0.2549 0.9923 0.053 Uiso 1 1 calc R . . C38 C 0.3581(4) 0.1063(8) 1.1595(5) 0.037(2) Uani 1 1 d . . . C39 C -0.0655(4) 0.2939(10) 0.6785(5) 0.055(3) Uani 1 1 d . . . H39 H -0.0561 0.2618 0.7308 0.066 Uiso 1 1 calc R . . C40 C -0.1111(3) 0.2674(11) 0.6081(5) 0.061(3) Uani 1 1 d . . . H40 H -0.1376 0.2118 0.6025 0.074 Uiso 1 1 calc R . . C41 C -0.0638(3) 0.3970(8) 0.5816(5) 0.044(2) Uani 1 1 d . . . H41 H -0.0526 0.4490 0.5524 0.053 Uiso 1 1 calc R . . C42 C -0.1511(3) 0.3378(8) 0.4614(5) 0.0313(19) Uani 1 1 d . . . C43 C -0.1503(4) 0.4235(11) 0.4099(5) 0.066(3) Uani 1 1 d . . . H43 H -0.1235 0.4821 0.4306 0.079 Uiso 1 1 calc R . . C44 C -0.1892(4) 0.4262(11) 0.3257(5) 0.064(3) Uani 1 1 d . . . H44 H -0.1880 0.4860 0.2911 0.077 Uiso 1 1 calc R . . C45 C -0.2295(3) 0.3395(8) 0.2940(5) 0.0322(19) Uani 1 1 d . . . C46 C -0.2292(4) 0.2543(11) 0.3467(5) 0.085(4) Uani 1 1 d . . . H46 H -0.2558 0.1954 0.3267 0.102 Uiso 1 1 calc R . . C47 C -0.1900(4) 0.2521(12) 0.4303(6) 0.080(4) Uani 1 1 d . . . H47 H -0.1907 0.1917 0.4648 0.096 Uiso 1 1 calc R . . C48 C -0.2711(3) 0.3428(8) 0.2043(5) 0.036(2) Uani 1 1 d . . . C49 C -0.2642(4) 0.4094(9) 0.1452(5) 0.057(3) Uani 1 1 d . . . H49 H -0.2320 0.4528 0.1619 0.069 Uiso 1 1 calc R . . C50 C -0.3026(3) 0.4142(8) 0.0634(5) 0.052(3) Uani 1 1 d . . . H50 H -0.2961 0.4572 0.0248 0.062 Uiso 1 1 calc R . . C51 C -0.3515(3) 0.3537(8) 0.0392(5) 0.034(2) Uani 1 1 d . . . C52 C -0.3589(3) 0.2845(9) 0.0948(5) 0.046(2) Uani 1 1 d . . . H52 H -0.3905 0.2390 0.0775 0.055 Uiso 1 1 calc R . . C53 C -0.3199(3) 0.2814(9) 0.1765(5) 0.040(2) Uani 1 1 d . . . H53 H -0.3265 0.2366 0.2144 0.048 Uiso 1 1 calc R . . C54 C -0.3974(3) 0.4504(10) -0.1004(5) 0.054(3) Uani 1 1 d . . . H54 H -0.3722 0.5105 -0.0920 0.064 Uiso 1 1 calc R . . C55 C -0.4454(3) 0.4327(9) -0.1696(5) 0.048(2) Uani 1 1 d . . . H55 H -0.4589 0.4800 -0.2171 0.058 Uiso 1 1 calc R . . C56 C -0.4372(3) 0.2962(8) -0.0835(5) 0.040(2) Uani 1 1 d . . . H56 H -0.4434 0.2291 -0.0592 0.049 Uiso 1 1 calc R . . Co1 Co 0.04563(4) -0.23462(16) 1.24577(6) 0.0265(3) Uani 1 1 d D . . Co2 Co 0.03932(4) 0.44703(17) 0.75055(6) 0.0262(3) Uani 1 1 d . . . N1 N 0.0949(2) -0.0867(6) 1.2431(4) 0.0333(17) Uani 1 1 d . . . N2 N 0.0865(2) 0.2913(6) 0.7575(4) 0.0327(16) Uani 1 1 d . . . N3 N -0.0351(2) 0.3752(6) 0.6611(4) 0.0284(15) Uani 1 1 d . . . N4 N -0.1109(2) 0.3372(6) 0.5468(4) 0.0293(16) Uani 1 1 d . . . N5 N -0.3932(3) 0.3656(6) -0.0467(4) 0.0360(17) Uani 1 1 d . . . N6 N -0.4709(2) 0.3352(6) -0.1593(4) 0.0309(16) Uani 1 1 d . . . O1 O 0.3569(2) 0.0461(6) 1.7222(3) 0.0487(17) Uani 1 1 d . . . O2 O 0.3872(2) 0.1821(5) 1.6642(3) 0.0371(14) Uani 1 1 d . . . O3 O 0.0364(2) 0.5318(5) 0.9331(3) 0.0378(14) Uani 1 1 d . . . O4 O 0.0256(2) 0.3832(5) 0.8442(3) 0.0386(14) Uani 1 1 d . . . O5 O 0.3622(3) 0.1584(8) 1.2231(4) 0.095(3) Uani 1 1 d . . . O6 O 0.3902(2) 0.0291(6) 1.1599(3) 0.0379(15) Uani 1 1 d . . . O7 O 0.0415(2) -0.2963(6) 0.4212(3) 0.0425(15) Uani 1 1 d . . . O8 O 0.0418(2) -0.1425(5) 0.3453(3) 0.0350(13) Uani 1 1 d . . . O9 O 0.0648(2) 0.5083(6) 0.6608(3) 0.0456(16) Uani 1 1 d D . . O10 O 0.0531(2) -0.3435(4) 1.1583(3) 0.0397(14) Uani 1 1 d D . . O11 O -0.0046(2) -0.3727(5) 1.2682(3) 0.0402(14) Uani 1 1 d D . . O12 O 1.0000 0.5800(8) 0.5000 0.050(2) Uani 1 2 d SD . . O13 O 0.2856(8) 0.238(2) 0.2772(13) 0.415(18) Uani 1 1 d D . . O14 O 0.2792(4) 0.9557(13) 0.7700(8) 0.165(5) Uani 1 1 d D . . H1W H 0.091(2) 0.551(6) 0.688(4) 0.080 Uiso 1 1 d D . . H3W H 0.0815(8) -0.381(4) 1.1704(12) 0.080 Uiso 1 1 d D . . H4W H 0.0258(3) -0.371(4) 1.1194(19) 0.080 Uiso 1 1 d D . . H2W H 0.053(3) 0.513(8) 0.6101(6) 0.080 Uiso 1 1 d D . . H9W H 0.2948(15) 0.266(7) 0.244(3) 0.550 Uiso 1 1 d D . . H5W H 0.0085(12) -0.382(3) 1.3188(4) 0.080 Uiso 1 1 d D . . H6W H -0.0365(3) -0.350(2) 1.246(3) 0.080 Uiso 1 1 d D . . H10W H 0.262(3) 0.276(7) 0.283(6) 0.550 Uiso 1 1 d D . . H12W H 0.3049(16) 0.979(8) 0.762(5) 0.080 Uiso 1 1 d D . . H11W H 0.288(3) 0.906(8) 0.807(5) 0.080 Uiso 1 1 d D . . H7W H 0.983(3) 0.619(7) 0.520(5) 0.080 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.021(4) 0.023(4) 0.025(4) -0.002(3) -0.001(3) -0.001(3) C2 0.029(4) 0.028(5) 0.022(4) 0.001(3) -0.001(4) -0.001(3) C3 0.032(4) 0.026(5) 0.020(4) 0.001(3) 0.013(4) 0.000(3) C4 0.040(5) 0.025(5) 0.030(5) 0.006(4) 0.010(4) -0.004(4) C5 0.022(4) 0.035(5) 0.014(4) 0.001(3) 0.000(3) 0.002(3) C6 0.023(4) 0.029(5) 0.023(4) 0.008(3) 0.004(4) 0.002(3) C7 0.035(5) 0.051(6) 0.024(5) 0.009(4) 0.001(4) -0.014(4) C8 0.031(5) 0.042(6) 0.033(5) -0.004(4) 0.006(4) -0.016(4) C9 0.024(4) 0.029(5) 0.028(5) -0.005(4) 0.005(4) 0.000(4) C10 0.056(6) 0.052(6) 0.028(5) 0.005(4) 0.003(5) -0.029(5) C11 0.060(6) 0.057(7) 0.030(5) -0.002(4) 0.002(5) -0.039(5) C12 0.026(4) 0.030(5) 0.032(5) -0.004(4) 0.001(4) 0.005(4) C13 0.031(4) 0.028(5) 0.019(4) 0.004(3) 0.010(4) 0.001(4) C14 0.043(5) 0.037(6) 0.016(4) -0.007(4) 0.002(4) -0.010(4) C15 0.056(6) 0.022(5) 0.026(5) 0.002(4) 0.010(5) 0.004(4) C16 0.027(4) 0.023(5) 0.026(4) 0.008(3) 0.008(4) 0.003(3) C17 0.047(5) 0.035(5) 0.009(4) 0.000(3) 0.002(4) 0.001(4) C18 0.049(5) 0.017(5) 0.040(5) 0.005(4) 0.017(5) 0.000(4) C19 0.023(4) 0.037(5) 0.018(4) 0.004(3) 0.000(3) 0.003(4) C20 0.032(4) 0.030(4) 0.024(4) -0.010(4) 0.006(4) 0.001(4) C21 0.030(4) 0.020(4) 0.021(4) -0.002(3) 0.010(4) 0.004(3) C22 0.029(4) 0.029(5) 0.026(4) 0.003(4) 0.005(4) 0.013(4) C23 0.034(4) 0.030(5) 0.022(4) -0.002(4) 0.005(4) 0.005(4) C24 0.032(4) 0.042(5) 0.019(4) -0.005(4) 0.005(4) -0.001(4) C25 0.027(4) 0.032(5) 0.021(4) -0.006(4) 0.003(4) 0.001(4) C26 0.064(6) 0.032(6) 0.020(4) -0.007(4) 0.006(5) -0.001(4) C27 0.064(6) 0.027(5) 0.030(5) -0.003(4) 0.019(5) 0.000(4) C28 0.035(5) 0.043(5) 0.014(4) 0.003(4) 0.007(4) -0.001(4) C29 0.055(6) 0.029(5) 0.034(5) 0.006(4) 0.021(5) 0.003(4) C30 0.033(5) 0.036(5) 0.023(4) 0.001(4) 0.007(4) -0.002(4) C31 0.029(4) 0.040(5) 0.028(5) -0.009(4) 0.012(4) -0.001(3) C32 0.032(4) 0.026(5) 0.022(4) 0.001(3) 0.006(4) 0.003(4) C33 0.039(5) 0.046(6) 0.017(4) 0.004(4) 0.005(4) 0.018(4) C34 0.033(5) 0.051(7) 0.028(5) 0.001(4) 0.003(4) 0.018(4) C35 0.021(4) 0.033(5) 0.031(5) 0.001(4) -0.002(4) 0.004(4) C36 0.046(5) 0.059(7) 0.020(5) -0.013(4) -0.002(4) 0.014(5) C37 0.040(5) 0.040(5) 0.036(5) -0.005(4) 0.003(4) 0.018(4) C38 0.047(5) 0.025(5) 0.027(5) -0.004(4) 0.008(4) -0.001(4) C39 0.054(6) 0.083(8) 0.020(4) 0.004(5) 0.009(4) -0.034(6) C40 0.054(5) 0.080(8) 0.024(5) 0.007(5) -0.005(4) -0.041(6) C41 0.035(5) 0.044(6) 0.036(6) 0.012(4) 0.002(5) -0.012(4) C42 0.026(4) 0.039(5) 0.019(4) -0.002(4) 0.002(4) 0.000(4) C43 0.060(6) 0.089(9) 0.025(5) -0.008(5) -0.002(5) -0.050(6) C44 0.063(6) 0.083(9) 0.030(5) 0.010(5) 0.008(5) -0.031(6) C45 0.021(4) 0.041(5) 0.027(5) -0.002(4) 0.005(4) -0.001(3) C46 0.063(6) 0.109(10) 0.029(5) 0.027(6) -0.025(5) -0.053(7) C47 0.064(6) 0.094(9) 0.035(5) 0.026(6) -0.018(5) -0.042(6) C48 0.026(4) 0.043(5) 0.032(5) 0.003(4) 0.007(4) -0.003(4) C49 0.043(5) 0.068(7) 0.037(5) 0.010(5) -0.003(4) -0.029(4) C50 0.042(5) 0.057(7) 0.037(5) 0.020(4) 0.001(4) -0.019(4) C51 0.024(4) 0.040(5) 0.026(5) -0.002(4) 0.000(4) 0.001(4) C52 0.040(5) 0.062(7) 0.029(5) 0.014(4) 0.010(4) -0.011(5) C53 0.030(4) 0.052(6) 0.022(4) 0.002(4) -0.001(4) -0.013(4) C54 0.053(5) 0.065(7) 0.031(5) 0.004(5) 0.009(5) -0.032(6) C55 0.042(5) 0.043(6) 0.033(5) 0.005(4) -0.006(4) -0.015(5) C56 0.036(5) 0.036(5) 0.026(5) -0.002(4) -0.006(4) -0.010(4) Co1 0.0267(5) 0.0235(6) 0.0179(5) 0.0007(4) 0.0002(5) -0.0012(4) Co2 0.0256(5) 0.0255(6) 0.0177(5) 0.0006(4) 0.0013(5) 0.0016(4) N1 0.027(3) 0.037(4) 0.025(3) 0.000(3) 0.003(3) -0.008(3) N2 0.031(3) 0.035(4) 0.021(3) -0.005(3) 0.002(3) 0.010(3) N3 0.028(3) 0.031(4) 0.015(3) 0.006(3) 0.000(3) -0.001(3) N4 0.026(3) 0.029(4) 0.024(4) 0.000(3) 0.004(3) -0.005(3) N5 0.031(4) 0.038(5) 0.029(4) 0.001(3) 0.005(3) -0.010(3) N6 0.024(3) 0.029(4) 0.028(4) 0.002(3) 0.001(3) -0.003(3) O1 0.053(4) 0.049(4) 0.024(3) 0.011(3) 0.001(3) -0.015(3) O2 0.039(3) 0.036(4) 0.024(3) -0.003(3) 0.003(3) -0.007(3) O3 0.049(4) 0.026(3) 0.032(3) 0.006(2) 0.013(3) 0.008(3) O4 0.042(3) 0.047(4) 0.017(3) 0.005(2) 0.005(3) -0.008(3) O5 0.092(6) 0.098(7) 0.040(4) -0.024(4) -0.019(4) 0.064(5) O6 0.027(3) 0.048(4) 0.030(3) 0.005(3) 0.005(3) 0.010(3) O7 0.060(4) 0.039(4) 0.031(3) -0.012(3) 0.023(3) -0.016(3) O8 0.043(3) 0.035(3) 0.020(3) -0.003(2) 0.008(3) 0.003(3) O9 0.038(3) 0.068(5) 0.031(3) -0.003(3) 0.015(3) -0.008(3) O10 0.037(3) 0.044(4) 0.028(3) -0.004(3) 0.006(3) 0.001(3) O11 0.039(3) 0.035(3) 0.031(3) -0.003(2) 0.003(2) -0.008(2) O12 0.061(6) 0.050(6) 0.046(5) 0.000 0.030(4) 0.000 O13 0.38(3) 0.65(5) 0.36(2) 0.26(3) 0.29(2) 0.11(3) O14 0.182(10) 0.163(13) 0.201(13) 0.060(10) 0.130(10) 0.007(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.356(9) . ? C1 C5 1.376(11) . ? C1 H1 0.9300 . ? C2 N1 1.314(9) . ? C2 C3 1.404(11) . ? C2 H2 0.9300 . ? C3 C4 1.403(10) . ? C3 C13 1.463(10) . ? C4 C5 1.372(11) . ? C4 H4 0.9300 . ? C5 C6 1.500(10) . ? C6 C7 1.371(11) . ? C6 C11 1.389(11) . ? C7 C8 1.371(10) . ? C7 H7 0.9300 . ? C8 C9 1.379(11) . ? C8 H8 0.9300 . ? C9 C10 1.363(11) . ? C9 C12 1.513(11) . ? C10 C11 1.406(11) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 O1 1.239(10) . ? C12 O2 1.260(10) . ? C13 C18 1.377(11) . ? C13 C14 1.398(12) . ? C14 C15 1.365(11) . ? C14 H14 0.9300 . ? C15 C16 1.367(11) . ? C15 H15 0.9300 . ? C16 C17 1.390(11) . ? C16 C19 1.504(10) . ? C17 C18 1.396(11) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 O3 1.252(10) . ? C19 O4 1.275(9) . ? C20 N2 1.322(9) . ? C20 C21 1.373(11) . ? C20 H20 0.9300 . ? C21 C22 1.399(10) . ? C21 C32 1.474(10) . ? C22 C23 1.382(10) . ? C22 H22 0.9300 . ? C23 C24 1.348(11) . ? C23 C25 1.491(10) . ? C24 N2 1.364(9) . ? C24 H24 0.9300 . ? C25 C26 1.369(12) . ? C25 C30 1.419(10) . ? C26 C27 1.395(11) . ? C26 H26 0.9300 . ? C27 C28 1.402(11) . ? C27 H27 0.9300 . ? C28 C29 1.375(11) . ? C28 C31 1.501(11) . ? C29 C30 1.369(11) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 O8 1.251(10) . ? C31 O7 1.259(10) . ? C32 C33 1.378(10) . ? C32 C37 1.384(11) . ? C33 C34 1.376(10) . ? C33 H33 0.9300 . ? C34 C35 1.378(11) . ? C34 H34 0.9300 . ? C35 C36 1.374(11) . ? C35 C38 1.503(11) . ? C36 C37 1.385(11) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 O6 1.234(10) . ? C38 O5 1.247(10) . ? C39 C40 1.348(11) . ? C39 N3 1.368(10) . ? C39 H39 0.9300 . ? C40 N4 1.358(10) . ? C40 H40 0.9300 . ? C41 N3 1.306(10) . ? C41 N4 1.333(10) . ? C41 H41 0.9300 . ? C42 C43 1.347(12) . ? C42 C47 1.357(13) . ? C42 N4 1.428(9) . ? C43 C44 1.402(11) . ? C43 H43 0.9300 . ? C44 C45 1.389(12) . ? C44 H44 0.9300 . ? C45 C46 1.348(12) . ? C45 C48 1.495(8) . ? C46 C47 1.396(11) . ? C46 H46 0.9300 . ? C47 H47 0.9300 . ? C48 C53 1.381(10) . ? C48 C49 1.384(11) . ? C49 C50 1.369(11) . ? C49 H49 0.9300 . ? C50 C51 1.384(10) . ? C50 H50 0.9300 . ? C51 C52 1.357(11) . ? C51 N5 1.452(9) . ? C52 C53 1.370(10) . ? C52 H52 0.9300 . ? C53 H53 0.9300 . ? C54 N5 1.328(11) . ? C54 C55 1.353(10) . ? C54 H54 0.9300 . ? C55 N6 1.360(11) . ? C55 H55 0.9300 . ? C56 N6 1.328(10) . ? C56 N5 1.332(10) . ? C56 H56 0.9300 . ? Co1 O2 2.045(5) 4_548 ? Co1 O10 2.081(5) . ? Co1 N6 2.082(6) 4_446 ? Co1 O8 2.117(5) 1_556 ? Co1 N1 2.160(6) . ? Co1 O11 2.234(5) . ? Co2 O4 2.021(5) . ? Co2 O6 2.086(5) 4_557 ? Co2 N3 2.101(6) . ? Co2 O9 2.147(5) . ? Co2 N2 2.151(6) . ? Co2 O11 2.206(5) 2_567 ? N6 Co1 2.082(6) 4_456 ? O2 Co1 2.045(5) 4_558 ? O6 Co2 2.086(5) 4_547 ? O8 Co1 2.117(5) 1_554 ? O9 H1W 0.8201(11) . ? O9 H2W 0.8200(11) . ? O10 H3W 0.8202(11) . ? O10 H4W 0.8202(11) . ? O11 Co2 2.206(5) 2_547 ? O11 H5W 0.8201(11) . ? O11 H6W 0.8201(11) . ? O12 H7W 0.8201(11) . ? O13 H9W 0.8200(11) . ? O13 H10W 0.8199(11) . ? O14 H12W 0.8200(13) . ? O14 H11W 0.8200(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C5 121.7(7) . . ? N1 C1 H1 119.2 . . ? C5 C1 H1 119.2 . . ? N1 C2 C3 123.5(7) . . ? N1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C4 C3 C2 115.6(7) . . ? C4 C3 C13 123.5(7) . . ? C2 C3 C13 120.8(7) . . ? C5 C4 C3 121.3(7) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C1 118.4(7) . . ? C4 C5 C6 123.0(7) . . ? C1 C5 C6 118.5(7) . . ? C7 C6 C11 116.3(8) . . ? C7 C6 C5 122.7(7) . . ? C11 C6 C5 121.0(7) . . ? C8 C7 C6 122.5(8) . . ? C8 C7 H7 118.7 . . ? C6 C7 H7 118.7 . . ? C7 C8 C9 121.1(8) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 118.0(8) . . ? C10 C9 C12 121.0(8) . . ? C8 C9 C12 120.8(7) . . ? C9 C10 C11 120.6(9) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C6 C11 C10 121.4(8) . . ? C6 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? O1 C12 O2 125.4(8) . . ? O1 C12 C9 120.4(8) . . ? O2 C12 C9 114.1(8) . . ? C18 C13 C14 117.7(7) . . ? C18 C13 C3 121.7(8) . . ? C14 C13 C3 120.5(7) . . ? C15 C14 C13 121.3(8) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 121.3(8) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C17 118.5(8) . . ? C15 C16 C19 121.4(7) . . ? C17 C16 C19 120.0(8) . . ? C16 C17 C18 120.3(8) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 120.8(8) . . ? C13 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? O3 C19 O4 125.3(7) . . ? O3 C19 C16 117.7(7) . . ? O4 C19 C16 117.1(7) . . ? N2 C20 C21 126.9(7) . . ? N2 C20 H20 116.5 . . ? C21 C20 H20 116.5 . . ? C20 C21 C22 114.3(7) . . ? C20 C21 C32 122.0(7) . . ? C22 C21 C32 123.7(7) . . ? C23 C22 C21 121.6(7) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 C23 C22 117.6(7) . . ? C24 C23 C25 121.4(7) . . ? C22 C23 C25 120.9(7) . . ? C23 C24 N2 123.8(7) . . ? C23 C24 H24 118.1 . . ? N2 C24 H24 118.1 . . ? C26 C25 C30 117.9(8) . . ? C26 C25 C23 122.7(8) . . ? C30 C25 C23 119.4(8) . . ? C25 C26 C27 121.0(8) . . ? C25 C26 H26 119.5 . . ? C27 C26 H26 119.5 . . ? C26 C27 C28 120.8(9) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C29 C28 C27 118.0(9) . . ? C29 C28 C31 120.8(8) . . ? C27 C28 C31 121.2(8) . . ? C30 C29 C28 121.6(9) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 119.2 . . ? C29 C30 C25 120.8(8) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? O8 C31 O7 123.7(8) . . ? O8 C31 C28 118.3(8) . . ? O7 C31 C28 118.0(8) . . ? C33 C32 C37 117.2(8) . . ? C33 C32 C21 121.5(7) . . ? C37 C32 C21 121.3(7) . . ? C32 C33 C34 120.6(7) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C35 C34 C33 122.1(8) . . ? C35 C34 H34 118.9 . . ? C33 C34 H34 118.9 . . ? C36 C35 C34 117.7(8) . . ? C36 C35 C38 122.3(8) . . ? C34 C35 C38 119.9(7) . . ? C35 C36 C37 120.3(8) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C32 C37 C36 122.0(8) . . ? C32 C37 H37 119.0 . . ? C36 C37 H37 119.0 . . ? O6 C38 O5 124.1(9) . . ? O6 C38 C35 116.5(7) . . ? O5 C38 C35 119.1(8) . . ? C40 C39 N3 109.4(7) . . ? C40 C39 H39 125.3 . . ? N3 C39 H39 125.3 . . ? C39 C40 N4 107.0(8) . . ? C39 C40 H40 126.5 . . ? N4 C40 H40 126.5 . . ? N3 C41 N4 113.1(8) . . ? N3 C41 H41 123.5 . . ? N4 C41 H41 123.5 . . ? C43 C42 C47 118.9(8) . . ? C43 C42 N4 120.0(7) . . ? C47 C42 N4 121.1(8) . . ? C42 C43 C44 121.2(8) . . ? C42 C43 H43 119.4 . . ? C44 C43 H43 119.4 . . ? C45 C44 C43 120.0(9) . . ? C45 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C46 C45 C44 117.6(8) . . ? C46 C45 C48 122.5(7) . . ? C44 C45 C48 119.9(7) . . ? C45 C46 C47 121.9(9) . . ? C45 C46 H46 119.1 . . ? C47 C46 H46 119.1 . . ? C42 C47 C46 120.4(9) . . ? C42 C47 H47 119.8 . . ? C46 C47 H47 119.8 . . ? C53 C48 C49 116.2(8) . . ? C53 C48 C45 120.9(7) . . ? C49 C48 C45 122.8(7) . . ? C50 C49 C48 122.9(8) . . ? C50 C49 H49 118.6 . . ? C48 C49 H49 118.6 . . ? C49 C50 C51 118.6(8) . . ? C49 C50 H50 120.7 . . ? C51 C50 H50 120.7 . . ? C52 C51 C50 119.9(8) . . ? C52 C51 N5 122.1(7) . . ? C50 C51 N5 117.9(7) . . ? C51 C52 C53 120.2(8) . . ? C51 C52 H52 119.9 . . ? C53 C52 H52 119.9 . . ? C52 C53 C48 121.9(8) . . ? C52 C53 H53 119.0 . . ? C48 C53 H53 119.1 . . ? N5 C54 C55 106.9(8) . . ? N5 C54 H54 126.5 . . ? C55 C54 H54 126.5 . . ? C54 C55 N6 109.7(8) . . ? C54 C55 H55 125.2 . . ? N6 C55 H55 125.2 . . ? N6 C56 N5 111.4(8) . . ? N6 C56 H56 124.3 . . ? N5 C56 H56 124.3 . . ? O2 Co1 O10 88.1(2) 4_548 . ? O2 Co1 N6 172.0(2) 4_548 4_446 ? O10 Co1 N6 93.4(2) . 4_446 ? O2 Co1 O8 85.8(2) 4_548 1_556 ? O10 Co1 O8 172.7(2) . 1_556 ? N6 Co1 O8 92.1(2) 4_446 1_556 ? O2 Co1 N1 91.6(2) 4_548 . ? O10 Co1 N1 99.3(2) . . ? N6 Co1 N1 95.8(3) 4_446 . ? O8 Co1 N1 84.9(2) 1_556 . ? O2 Co1 O11 86.6(2) 4_548 . ? O10 Co1 O11 90.35(19) . . ? N6 Co1 O11 85.6(2) 4_446 . ? O8 Co1 O11 85.25(19) 1_556 . ? N1 Co1 O11 170.1(2) . . ? O4 Co2 O6 88.3(2) . 4_557 ? O4 Co2 N3 91.1(2) . . ? O6 Co2 N3 175.7(3) 4_557 . ? O4 Co2 O9 172.5(2) . . ? O6 Co2 O9 86.3(2) 4_557 . ? N3 Co2 O9 94.6(2) . . ? O4 Co2 N2 89.7(2) . . ? O6 Co2 N2 89.9(2) 4_557 . ? N3 Co2 N2 94.4(3) . . ? O9 Co2 N2 85.1(2) . . ? O4 Co2 O11 103.1(2) . 2_567 ? O6 Co2 O11 83.7(2) 4_557 2_567 ? N3 Co2 O11 92.2(2) . 2_567 ? O9 Co2 O11 81.5(2) . 2_567 ? N2 Co2 O11 165.5(2) . 2_567 ? C2 N1 C1 119.5(7) . . ? C2 N1 Co1 126.8(5) . . ? C1 N1 Co1 113.2(5) . . ? C20 N2 C24 115.7(7) . . ? C20 N2 Co2 119.0(5) . . ? C24 N2 Co2 125.2(5) . . ? C41 N3 C39 104.6(7) . . ? C41 N3 Co2 131.2(6) . . ? C39 N3 Co2 124.2(5) . . ? C41 N4 C40 105.7(7) . . ? C41 N4 C42 127.6(7) . . ? C40 N4 C42 126.4(7) . . ? C54 N5 C56 107.5(7) . . ? C54 N5 C51 127.5(7) . . ? C56 N5 C51 124.8(7) . . ? C56 N6 C55 104.4(7) . . ? C56 N6 Co1 129.1(6) . 4_456 ? C55 N6 Co1 126.5(5) . 4_456 ? C12 O2 Co1 136.7(6) . 4_558 ? C19 O4 Co2 129.9(5) . . ? C38 O6 Co2 136.4(6) . 4_547 ? C31 O8 Co1 125.5(5) . 1_554 ? Co2 O9 H1W 104(5) . . ? Co2 O9 H2W 140(5) . . ? H1W O9 H2W 114.6(2) . . ? Co1 O10 H3W 120.6(5) . . ? Co1 O10 H4W 120.6(5) . . ? H3W O10 H4W 114.5(2) . . ? Co2 O11 Co1 150.9(2) 2_547 . ? Co2 O11 H5W 89.8(16) 2_547 . ? Co1 O11 H5W 107.1(4) . . ? Co2 O11 H6W 86.0(17) 2_547 . ? Co1 O11 H6W 107.1(4) . . ? H5W O11 H6W 114.6(2) . . ? H9W O13 H10W 114.6(2) . . ? H12W O14 H11W 114.6(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.447 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 932486' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 Cu N3 O5' _chemical_formula_sum 'C28 H20 Cu N3 O5' _chemical_formula_weight 542.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.386(2) _cell_length_b 11.3957(10) _cell_length_c 17.5666(19) _cell_angle_alpha 90.00 _cell_angle_beta 115.7120(10) _cell_angle_gamma 90.00 _cell_volume 4759.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1107 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 20.64 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7946 _exptl_absorpt_correction_T_max 0.9269 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 12024 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4185 _reflns_number_gt 2576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^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 4185 _refine_ls_number_parameters 340 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1123 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1987 _refine_ls_wR_factor_gt 0.1649 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 C1 C 0.3593(2) 0.9948(5) 0.9133(4) 0.0268(13) Uani 1 1 d . . . C2 C 0.3115(2) 0.9728(5) 0.8286(4) 0.0279(14) Uani 1 1 d . . . C3 C 0.2664(3) 0.9012(6) 0.8205(4) 0.0404(17) Uani 1 1 d . . . H3 H 0.2670 0.8634 0.8678 0.049 Uiso 1 1 calc R . . C4 C 0.2214(3) 0.8860(6) 0.7440(4) 0.0417(17) Uani 1 1 d . . . H4 H 0.1913 0.8400 0.7403 0.050 Uiso 1 1 calc R . . C5 C 0.2197(2) 0.9387(5) 0.6707(4) 0.0291(14) Uani 1 1 d . . . C6 C 0.2637(3) 1.0101(6) 0.6795(4) 0.0371(16) Uani 1 1 d . . . H6 H 0.2630 1.0483 0.6323 0.044 Uiso 1 1 calc R . . C7 C 0.3087(3) 1.0267(6) 0.7567(4) 0.0368(16) Uani 1 1 d . . . H7 H 0.3380 1.0753 0.7605 0.044 Uiso 1 1 calc R . . C8 C 0.1709(2) 0.9221(5) 0.5870(3) 0.0279(14) Uani 1 1 d . . . C9 C 0.1360(3) 0.8253(5) 0.5715(4) 0.0347(15) Uani 1 1 d . . . H9 H 0.1442 0.7715 0.6151 0.042 Uiso 1 1 calc R . . C10 C 0.0798(3) 0.8813(5) 0.4363(4) 0.0345(15) Uani 1 1 d . . . H10 H 0.0486 0.8676 0.3853 0.041 Uiso 1 1 calc R . . C11 C 0.1114(2) 0.9815(5) 0.4433(4) 0.0306(14) Uani 1 1 d . . . C12 C 0.1573(3) 1.0000(5) 0.5205(4) 0.0325(14) Uani 1 1 d . . . H12 H 0.1794 1.0664 0.5278 0.039 Uiso 1 1 calc R . . C13 C 0.0960(3) 1.0652(5) 0.3722(4) 0.0313(14) Uani 1 1 d . . . C14 C 0.0757(3) 1.0290(6) 0.2897(4) 0.0358(15) Uani 1 1 d . . . H14 H 0.0728 0.9490 0.2780 0.043 Uiso 1 1 calc R . . C15 C 0.0593(2) 1.1074(5) 0.2234(4) 0.0330(15) Uani 1 1 d . . . H15 H 0.0460 1.0797 0.1683 0.040 Uiso 1 1 calc R . . C16 C 0.0627(2) 1.2274(5) 0.2385(3) 0.0280(14) Uani 1 1 d . . . C17 C 0.0838(3) 1.2659(6) 0.3217(4) 0.0351(15) Uani 1 1 d . . . H17 H 0.0863 1.3461 0.3327 0.042 Uiso 1 1 calc R . . C18 C 0.1009(3) 1.1879(6) 0.3883(4) 0.0384(16) Uani 1 1 d . . . H18 H 0.1157 1.2156 0.4435 0.046 Uiso 1 1 calc R . . C19 C 0.0421(2) 1.3155(6) 0.1674(4) 0.0305(14) Uani 1 1 d . . . C20 C -0.0576(3) 0.8131(6) 0.4301(4) 0.0425(17) Uani 1 1 d . . . H20 H -0.0447 0.8556 0.4802 0.051 Uiso 1 1 calc R . . C21 C -0.1019(3) 0.8420(6) 0.3584(4) 0.0428(17) Uani 1 1 d . . . H21 H -0.1250 0.9071 0.3495 0.051 Uiso 1 1 calc R . . C22 C -0.0649(3) 0.6804(5) 0.3401(4) 0.0336(15) Uani 1 1 d . . . H22 H -0.0589 0.6138 0.3145 0.040 Uiso 1 1 calc R . . C23 C -0.1482(2) 0.7528(5) 0.2142(4) 0.0291(14) Uani 1 1 d . . . C24 C -0.1413(3) 0.6819(6) 0.1561(4) 0.0418(17) Uani 1 1 d . . . H24 H -0.1095 0.6348 0.1726 0.050 Uiso 1 1 calc R . . C25 C -0.1814(3) 0.6807(6) 0.0737(4) 0.0406(17) Uani 1 1 d . . . H25 H -0.1764 0.6302 0.0360 0.049 Uiso 1 1 calc R . . C26 C -0.2288(2) 0.7509(5) 0.0440(3) 0.0290(14) Uani 1 1 d . . . C27 C -0.2338(3) 0.8216(6) 0.1040(4) 0.050(2) Uani 1 1 d . . . H27 H -0.2650 0.8702 0.0876 0.060 Uiso 1 1 calc R . . C28 C -0.1944(3) 0.8237(7) 0.1877(4) 0.053(2) Uani 1 1 d . . . H28 H -0.1994 0.8734 0.2258 0.064 Uiso 1 1 calc R . . Cu1 Cu 0.03831(3) 0.64363(6) 0.50218(4) 0.0281(3) Uani 1 1 d . . . N1 N 0.0913(2) 0.8039(4) 0.4981(3) 0.0327(12) Uani 1 1 d . . . N2 N -0.0341(2) 0.7107(4) 0.4187(3) 0.0308(12) Uani 1 1 d . . . N3 N -0.10662(19) 0.7583(4) 0.3011(3) 0.0302(12) Uani 1 1 d . . . O1 O 0.39576(17) 1.0685(4) 0.9120(2) 0.0390(11) Uani 1 1 d . . . O2 O 0.36186(19) 0.9440(4) 0.9772(3) 0.0513(13) Uani 1 1 d . . . O3 O 0.03801(18) 1.4194(4) 0.1863(3) 0.0392(11) Uani 1 1 d . . . O4 O 0.02912(17) 1.2750(4) 0.0947(2) 0.0367(11) Uani 1 1 d . . . O5 O 0.04529(18) 0.5485(4) 0.4137(3) 0.0406(11) Uani 1 1 d D . . H1W H 0.0733(11) 0.506(3) 0.431(5) 0.080 Uiso 1 1 d D . . H2W H 0.0158(11) 0.514(4) 0.403(5) 0.080 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(3) 0.025(3) 0.021(3) -0.004(3) 0.004(3) 0.001(3) C2 0.026(3) 0.024(3) 0.025(3) -0.004(3) 0.003(3) -0.001(3) C3 0.045(4) 0.039(4) 0.025(4) 0.007(3) 0.003(3) -0.006(3) C4 0.030(4) 0.047(4) 0.032(4) 0.004(3) -0.002(3) -0.015(3) C5 0.027(3) 0.029(3) 0.022(3) -0.002(3) 0.001(3) -0.001(3) C6 0.039(4) 0.040(4) 0.022(3) 0.001(3) 0.004(3) -0.015(3) C7 0.032(4) 0.038(4) 0.035(4) -0.001(3) 0.009(3) -0.011(3) C8 0.025(3) 0.024(3) 0.024(3) -0.004(3) 0.000(3) 0.003(3) C9 0.035(4) 0.034(4) 0.022(3) 0.001(3) 0.000(3) -0.001(3) C10 0.035(4) 0.037(4) 0.019(3) -0.001(3) 0.000(3) -0.005(3) C11 0.035(4) 0.031(3) 0.024(3) 0.000(3) 0.012(3) 0.001(3) C12 0.037(4) 0.031(3) 0.022(3) 0.000(3) 0.005(3) -0.004(3) C13 0.036(4) 0.028(3) 0.026(3) 0.006(3) 0.010(3) 0.002(3) C14 0.038(4) 0.031(4) 0.033(4) 0.001(3) 0.011(3) 0.007(3) C15 0.033(4) 0.040(4) 0.018(3) 0.000(3) 0.003(3) 0.003(3) C16 0.026(3) 0.032(3) 0.019(3) 0.005(3) 0.004(3) 0.000(3) C17 0.050(4) 0.026(3) 0.026(3) 0.002(3) 0.013(3) 0.001(3) C18 0.046(4) 0.038(4) 0.018(3) 0.001(3) 0.002(3) 0.002(3) C19 0.026(3) 0.035(4) 0.020(3) 0.007(3) 0.000(3) -0.002(3) C20 0.042(4) 0.046(4) 0.023(4) -0.004(3) -0.001(3) 0.010(3) C21 0.046(4) 0.043(4) 0.025(3) -0.011(3) 0.002(3) 0.015(3) C22 0.034(4) 0.026(3) 0.028(4) -0.007(3) 0.002(3) 0.003(3) C23 0.028(3) 0.031(3) 0.020(3) 0.001(3) 0.002(3) -0.001(3) C24 0.035(4) 0.049(4) 0.027(4) -0.002(3) 0.000(3) 0.017(3) C25 0.040(4) 0.048(4) 0.023(3) -0.005(3) 0.003(3) 0.012(3) C26 0.030(3) 0.030(3) 0.020(3) 0.000(3) 0.004(3) -0.001(3) C27 0.037(4) 0.056(5) 0.030(4) -0.009(3) -0.010(3) 0.025(3) C28 0.053(5) 0.058(5) 0.025(4) -0.011(3) -0.005(3) 0.025(4) Cu1 0.0283(4) 0.0277(4) 0.0160(4) -0.0014(3) -0.0020(3) 0.0019(3) N1 0.031(3) 0.033(3) 0.024(3) 0.001(2) 0.003(2) -0.002(2) N2 0.028(3) 0.032(3) 0.021(3) -0.001(2) 0.000(2) 0.002(2) N3 0.025(3) 0.033(3) 0.019(3) 0.003(2) -0.003(2) 0.003(2) O1 0.039(3) 0.042(3) 0.021(2) 0.000(2) -0.0003(19) -0.013(2) O2 0.044(3) 0.066(3) 0.029(3) 0.009(2) 0.002(2) -0.020(3) O3 0.043(3) 0.032(3) 0.030(2) 0.006(2) 0.004(2) 0.005(2) O4 0.040(3) 0.038(3) 0.019(2) 0.0014(19) 0.0005(19) -0.011(2) O5 0.035(2) 0.040(3) 0.032(3) -0.011(2) 0.001(2) 0.004(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 C1 O2 1.238(7) . ? C1 O1 1.285(7) . ? C1 C2 1.497(7) . ? C2 C7 1.377(8) . ? C2 C3 1.399(8) . ? C3 C4 1.364(8) . ? C3 H3 0.9300 . ? C4 C5 1.403(8) . ? C4 H4 0.9300 . ? C5 C6 1.371(8) . ? C5 C8 1.488(7) . ? C6 C7 1.374(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.386(8) . ? C8 C12 1.384(8) . ? C9 N1 1.339(7) . ? C9 H9 0.9300 . ? C10 N1 1.327(7) . ? C10 C11 1.388(8) . ? C10 H10 0.9300 . ? C11 C12 1.388(8) . ? C11 C13 1.481(8) . ? C12 H12 0.9300 . ? C13 C14 1.373(8) . ? C13 C18 1.422(9) . ? C14 C15 1.380(8) . ? C14 H14 0.9300 . ? C15 C16 1.389(8) . ? C15 H15 0.9300 . ? C16 C17 1.390(8) . ? C16 C19 1.508(8) . ? C17 C18 1.380(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 O3 1.246(7) . ? C19 O4 1.259(7) . ? C20 C21 1.335(9) . ? C20 N2 1.377(8) . ? C20 H20 0.9300 . ? C21 N3 1.352(7) . ? C21 H21 0.9300 . ? C22 N2 1.310(7) . ? C22 N3 1.347(7) . ? C22 H22 0.9300 . ? C23 C28 1.365(9) . ? C23 C24 1.374(8) . ? C23 N3 1.444(7) . ? C24 C25 1.373(8) . ? C24 H24 0.9300 . ? C25 C26 1.383(8) . ? C25 H25 0.9300 . ? C26 C27 1.377(9) . ? C26 C26 1.464(11) 7_465 ? C27 C28 1.383(8) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? Cu1 O1 1.938(4) 4_546 ? Cu1 O4 1.975(4) 6_576 ? Cu1 O5 1.968(4) . ? Cu1 N2 1.988(5) . ? Cu1 N1 2.320(5) . ? O1 Cu1 1.938(4) 4_556 ? O4 Cu1 1.975(4) 6_575 ? O5 H1W 0.8203(19) . ? O5 H2W 0.820(4) . ? 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 C1 O1 125.1(5) . . ? O2 C1 C2 120.9(5) . . ? O1 C1 C2 114.0(5) . . ? C7 C2 C3 117.6(5) . . ? C7 C2 C1 121.6(5) . . ? C3 C2 C1 120.8(5) . . ? C4 C3 C2 120.8(6) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 121.2(6) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 117.5(5) . . ? C6 C5 C8 120.9(5) . . ? C4 C5 C8 121.5(5) . . ? C7 C6 C5 121.4(6) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C2 C7 C6 121.5(6) . . ? C2 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C9 C8 C12 116.0(5) . . ? C9 C8 C5 120.7(5) . . ? C12 C8 C5 123.3(5) . . ? N1 C9 C8 124.5(6) . . ? N1 C9 H9 117.8 . . ? C8 C9 H9 117.8 . . ? N1 C10 C11 124.0(5) . . ? N1 C10 H10 118.0 . . ? C11 C10 H10 118.0 . . ? C10 C11 C12 116.6(5) . . ? C10 C11 C13 121.4(5) . . ? C12 C11 C13 122.0(6) . . ? C11 C12 C8 121.6(6) . . ? C11 C12 H12 119.2 . . ? C8 C12 H12 119.2 . . ? C14 C13 C18 117.7(5) . . ? C14 C13 C11 122.4(6) . . ? C18 C13 C11 119.9(5) . . ? C13 C14 C15 122.2(6) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? C14 C15 C16 120.3(6) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 118.4(5) . . ? C17 C16 C19 119.7(5) . . ? C15 C16 C19 121.8(5) . . ? C18 C17 C16 121.5(6) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C13 119.8(6) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? O3 C19 O4 127.0(5) . . ? O3 C19 C16 117.0(5) . . ? O4 C19 C16 116.0(6) . . ? C21 C20 N2 109.7(6) . . ? C21 C20 H20 125.2 . . ? N2 C20 H20 125.2 . . ? C20 C21 N3 106.8(6) . . ? C20 C21 H21 126.6 . . ? N3 C21 H21 126.6 . . ? N2 C22 N3 111.0(5) . . ? N2 C22 H22 124.5 . . ? N3 C22 H22 124.5 . . ? C28 C23 C24 118.7(6) . . ? C28 C23 N3 119.4(6) . . ? C24 C23 N3 121.8(5) . . ? C23 C24 C25 119.9(6) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 123.3(6) . . ? C24 C25 H25 118.4 . . ? C26 C25 H25 118.3 . . ? C27 C26 C25 114.9(5) . . ? C27 C26 C26 122.4(7) . 7_465 ? C25 C26 C26 122.8(7) . 7_465 ? C26 C27 C28 123.1(6) . . ? C26 C27 H27 118.5 . . ? C28 C27 H27 118.5 . . ? C23 C28 C27 120.1(6) . . ? C23 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? O1 Cu1 O4 87.52(17) 4_546 6_576 ? O1 Cu1 O5 90.61(17) 4_546 . ? O4 Cu1 O5 174.43(19) 6_576 . ? O1 Cu1 N2 173.97(19) 4_546 . ? O4 Cu1 N2 90.26(18) 6_576 . ? O5 Cu1 N2 91.08(19) . . ? O1 Cu1 N1 91.27(18) 4_546 . ? O4 Cu1 N1 86.92(18) 6_576 . ? O5 Cu1 N1 98.36(19) . . ? N2 Cu1 N1 94.21(19) . . ? C10 N1 C9 117.4(5) . . ? C10 N1 Cu1 128.4(4) . . ? C9 N1 Cu1 113.9(4) . . ? C22 N2 C20 105.3(5) . . ? C22 N2 Cu1 129.4(4) . . ? C20 N2 Cu1 124.7(4) . . ? C22 N3 C21 107.2(5) . . ? C22 N3 C23 125.9(5) . . ? C21 N3 C23 126.9(5) . . ? C1 O1 Cu1 134.5(4) . 4_556 ? C19 O4 Cu1 125.9(4) . 6_575 ? Cu1 O5 H1W 114(5) . . ? Cu1 O5 H2W 92(5) . . ? H1W O5 H2W 114.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.914 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 932488' ####################################################################### # # 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_p _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H31 Ni N5 O5, 2(H2 O)' _chemical_formula_sum 'C39 H35 N5 Ni O7' _chemical_formula_weight 744.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 32.498(8) _cell_length_b 12.812(3) _cell_length_c 18.172(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.661(5) _cell_angle_gamma 90.00 _cell_volume 7541(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6577 _cell_measurement_theta_min 1.71 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3104 _exptl_absorpt_coefficient_mu 0.569 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9348 _exptl_absorpt_correction_T_max 0.9559 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 17912 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6577 _reflns_number_gt 3812 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1914P)^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 6577 _refine_ls_number_parameters 470 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.2864 _refine_ls_wR_factor_gt 0.2414 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Ni1 Ni 0.39431(2) 0.80396(6) -0.10956(4) 0.0411(3) Uani 1 1 d . . . O1 O 0.45397(12) 0.7633(3) -0.0720(3) 0.0579(12) Uani 1 1 d . . . O3 O 0.83473(11) 0.6518(3) 0.3509(2) 0.0420(9) Uani 1 1 d . . . O2 O 0.46847(17) 0.8890(4) 0.0116(4) 0.099(2) Uani 1 1 d . . . O4 O 0.83329(12) 0.4906(4) 0.3935(3) 0.0616(13) Uani 1 1 d . . . N5 N 0.61949(13) 0.3544(4) 0.1330(3) 0.0433(12) Uani 1 1 d . . . C8 C 0.65285(16) 0.3836(4) 0.1753(3) 0.0392(13) Uani 1 1 d . . . H8 H 0.6708 0.3320 0.1944 0.047 Uiso 1 1 calc R . . N1 N 0.37533(17) 0.7844(4) -0.0032(3) 0.0540(14) Uani 1 1 d . . . C2 C 0.77641(15) 0.5487(4) 0.3173(3) 0.0365(13) Uani 1 1 d . . . C5 C 0.70089(15) 0.5110(5) 0.2383(3) 0.0371(13) Uani 1 1 d . . . C9 C 0.66239(15) 0.4863(5) 0.1924(3) 0.0361(13) Uani 1 1 d . . . C6 C 0.72099(17) 0.6033(5) 0.2311(3) 0.0441(14) Uani 1 1 d . . . H6 H 0.7093 0.6542 0.1994 0.053 Uiso 1 1 calc R . . C7 C 0.75852(17) 0.6223(5) 0.2701(3) 0.0446(15) Uani 1 1 d . . . H7 H 0.7718 0.6857 0.2642 0.054 Uiso 1 1 calc R . . C14 C 0.54951(17) 0.5810(5) 0.0120(3) 0.0490(16) Uani 1 1 d . . . H14 H 0.5547 0.5177 -0.0106 0.059 Uiso 1 1 calc R . . C10 C 0.63643(15) 0.5620(5) 0.1597(3) 0.0421(14) Uani 1 1 d . . . H10 H 0.6420 0.6322 0.1685 0.050 Uiso 1 1 calc R . . C11 C 0.60194(15) 0.5329(5) 0.1135(3) 0.0436(14) Uani 1 1 d . . . C1 C 0.81818(15) 0.5656(5) 0.3576(3) 0.0394(14) Uani 1 1 d . . . C3 C 0.75543(17) 0.4587(5) 0.3270(4) 0.0522(17) Uani 1 1 d . . . H3 H 0.7665 0.4097 0.3607 0.063 Uiso 1 1 calc R . . C13 C 0.57288(15) 0.6082(5) 0.0766(3) 0.0448(15) Uani 1 1 d . . . C19 C 0.4749(2) 0.8028(6) -0.0183(5) 0.065(2) Uani 1 1 d . . . N4 N 0.08797(17) 1.3153(5) -0.2843(3) 0.0620(16) Uani 1 1 d . . . C4 C 0.71823(18) 0.4383(5) 0.2879(4) 0.0532(17) Uani 1 1 d . . . H4 H 0.7047 0.3756 0.2949 0.064 Uiso 1 1 calc R . . N3 N 0.0881(2) 1.3319(6) -0.1656(4) 0.0756(19) Uani 1 1 d . . . C12 C 0.59557(16) 0.4277(5) 0.1036(3) 0.0434(14) Uani 1 1 d . . . H12 H 0.5724 0.4071 0.0737 0.052 Uiso 1 1 calc R . . C16 C 0.51104(18) 0.7384(5) 0.0117(4) 0.0577(18) Uani 1 1 d . . . C18 C 0.5652(2) 0.7053(6) 0.1076(4) 0.072(2) Uani 1 1 d . . . H18 H 0.5808 0.7266 0.1502 0.086 Uiso 1 1 calc R . . C17 C 0.5352(2) 0.7693(6) 0.0759(5) 0.081(3) Uani 1 1 d . . . H17 H 0.5307 0.8340 0.0970 0.097 Uiso 1 1 calc R . . C27 C 0.2180(2) 1.0342(8) 0.0308(4) 0.074(2) Uani 1 1 d . . . C15 C 0.51917(18) 0.6446(5) -0.0193(4) 0.0547(17) Uani 1 1 d . . . H15 H 0.5039 0.6235 -0.0622 0.066 Uiso 1 1 calc R . . N2 N 0.3364(2) 0.7876(7) 0.0869(4) 0.089(2) Uani 1 1 d . . . C30 C 0.1888(3) 1.1134(7) -0.0017(4) 0.078(2) Uani 1 1 d . . . C20 C 0.3419(2) 0.8204(7) 0.0204(4) 0.069(2) Uani 1 1 d . . . H20 H 0.3238 0.8647 -0.0068 0.083 Uiso 1 1 calc R . . C28 C 0.2081(3) 0.9325(8) 0.0336(5) 0.080(2) Uani 1 1 d . . . H28 H 0.1822 0.9108 0.0139 0.096 Uiso 1 1 calc R . . C37 C 0.1088(3) 1.3434(7) -0.2229(5) 0.074(2) Uani 1 1 d . . . H37 H 0.1357 1.3690 -0.2207 0.088 Uiso 1 1 calc R . . C25 C 0.2830(3) 0.9826(14) 0.0972(6) 0.119(5) Uani 1 1 d . . . H25 H 0.3087 1.0001 0.1202 0.142 Uiso 1 1 calc R . . C34 C 0.1627(4) 1.2860(8) -0.0021(5) 0.095(3) Uani 1 1 d . . . H34 H 0.1646 1.3534 0.0168 0.114 Uiso 1 1 calc R . . C35 C 0.1889(4) 1.2109(9) 0.0269(5) 0.102(3) Uani 1 1 d . . . H35 H 0.2073 1.2270 0.0672 0.123 Uiso 1 1 calc R . . C29 C 0.2351(3) 0.8604(9) 0.0647(5) 0.093(3) Uani 1 1 d . . . H29 H 0.2274 0.7904 0.0639 0.112 Uiso 1 1 calc R . . C26 C 0.2563(3) 1.0672(11) 0.0629(6) 0.113(4) Uani 1 1 d . . . H26 H 0.2645 1.1367 0.0630 0.136 Uiso 1 1 calc R . . C39 C 0.0524(4) 1.2951(12) -0.1882(8) 0.145(6) Uani 1 1 d . . . H39 H 0.0306 1.2812 -0.1595 0.174 Uiso 1 1 calc R . . C31 C 0.1600(3) 1.0917(7) -0.0606(5) 0.082(2) Uani 1 1 d . . . H31 H 0.1594 1.0253 -0.0814 0.098 Uiso 1 1 calc R . . C22 C 0.3688(3) 0.7233(9) 0.1067(5) 0.100(3) Uani 1 1 d . . . H22 H 0.3736 0.6878 0.1513 0.120 Uiso 1 1 calc R . . C33 C 0.1342(3) 1.2636(7) -0.0577(5) 0.079(2) Uani 1 1 d . . . C21 C 0.3917(3) 0.7209(7) 0.0513(5) 0.087(3) Uani 1 1 d . . . H21 H 0.4157 0.6817 0.0493 0.104 Uiso 1 1 calc R . . C23 C 0.3013(3) 0.8084(13) 0.1322(7) 0.142(6) Uani 1 1 d . . . H23A H 0.3118 0.8344 0.1802 0.170 Uiso 1 1 calc R . . H23B H 0.2867 0.7436 0.1396 0.170 Uiso 1 1 calc R . . C24 C 0.2718(3) 0.8865(12) 0.0960(5) 0.100(3) Uani 1 1 d . . . C36 C 0.1041(4) 1.3425(9) -0.0872(5) 0.101(3) Uani 1 1 d . . . H36A H 0.1168 1.4107 -0.0809 0.122 Uiso 1 1 calc R . . H36B H 0.0807 1.3410 -0.0572 0.122 Uiso 1 1 calc R . . C32 C 0.1334(3) 1.1637(9) -0.0880(5) 0.090(3) Uani 1 1 d . . . H32 H 0.1143 1.1472 -0.1271 0.108 Uiso 1 1 calc R . . C38 C 0.0530(3) 1.2804(11) -0.2625(7) 0.122(4) Uani 1 1 d . . . H38 H 0.0318 1.2502 -0.2930 0.146 Uiso 1 1 calc R . . O1W O 0.41182(13) 0.9582(3) -0.0894(3) 0.0663(14) Uani 1 1 d . . . H1WA H 0.4269 0.9819 -0.0490 0.099 Uiso 1 1 d R . . H1WB H 0.4055 1.0128 -0.1194 0.099 Uiso 1 1 d R . . O2W O 0.8548(3) 0.3259(6) 0.2911(5) 0.166(4) Uani 1 1 d G . . H2WA H 0.8739 0.2973 0.3188 0.249 Uiso 1 1 d G . . H2WB H 0.8390 0.2791 0.2712 0.249 Uiso 1 1 d G . . O4W O 0.4900(3) 0.0141(11) 0.1254(8) 0.373(14) Uani 1 1 d G . . H4WA H 0.5110 0.0273 0.1020 0.559 Uiso 1 1 d G . . H4WB H 0.4968 0.0165 0.1716 0.559 Uiso 1 1 d G . . 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 0.0260(4) 0.0379(5) 0.0564(5) 0.0003(3) -0.0152(3) 0.0020(3) O1 0.034(2) 0.042(3) 0.092(3) 0.001(2) -0.028(2) 0.0003(19) O3 0.0272(19) 0.041(2) 0.055(2) -0.0014(19) -0.0146(17) -0.0054(17) O2 0.076(4) 0.055(4) 0.152(5) -0.038(3) -0.077(4) 0.024(3) O4 0.040(2) 0.054(3) 0.085(3) 0.022(2) -0.030(2) -0.013(2) N5 0.027(2) 0.043(3) 0.056(3) -0.001(2) -0.019(2) 0.003(2) C8 0.027(3) 0.036(3) 0.052(3) -0.004(3) -0.014(2) 0.001(2) N1 0.052(3) 0.059(4) 0.047(3) 0.003(2) -0.017(3) -0.002(3) C2 0.025(3) 0.037(3) 0.045(3) 0.001(2) -0.009(2) -0.004(2) C5 0.024(3) 0.043(3) 0.043(3) -0.005(2) -0.011(2) 0.000(2) C9 0.021(2) 0.042(3) 0.043(3) -0.001(2) -0.010(2) 0.001(2) C6 0.034(3) 0.037(3) 0.058(4) 0.003(3) -0.020(3) -0.001(3) C7 0.035(3) 0.040(4) 0.057(4) 0.000(3) -0.013(3) -0.011(3) C14 0.040(3) 0.041(4) 0.063(4) -0.004(3) -0.017(3) 0.007(3) C10 0.026(3) 0.040(4) 0.057(4) -0.005(3) -0.012(2) -0.002(2) C11 0.028(3) 0.045(4) 0.056(4) -0.005(3) -0.011(3) 0.005(2) C1 0.025(3) 0.046(4) 0.044(3) -0.001(3) -0.013(2) -0.003(3) C3 0.036(3) 0.050(4) 0.065(4) 0.016(3) -0.023(3) -0.004(3) C13 0.023(3) 0.040(4) 0.069(4) 0.000(3) -0.016(3) -0.001(2) C19 0.042(4) 0.046(4) 0.099(6) 0.000(4) -0.037(4) -0.003(3) N4 0.040(3) 0.066(4) 0.079(4) -0.014(3) -0.002(3) 0.006(3) C4 0.041(3) 0.049(4) 0.065(4) 0.010(3) -0.020(3) -0.020(3) N3 0.068(4) 0.085(5) 0.078(5) -0.016(4) 0.029(4) -0.009(4) C12 0.027(3) 0.043(4) 0.057(4) -0.008(3) -0.012(2) 0.000(2) C16 0.034(3) 0.042(4) 0.091(5) -0.002(4) -0.029(3) 0.002(3) C18 0.051(4) 0.062(5) 0.093(6) -0.022(4) -0.045(4) 0.010(3) C17 0.057(4) 0.041(4) 0.136(7) -0.029(4) -0.051(5) 0.016(3) C27 0.065(5) 0.096(7) 0.064(5) -0.018(4) 0.025(4) -0.026(5) C15 0.040(3) 0.055(4) 0.065(4) 0.001(3) -0.025(3) -0.001(3) N2 0.065(4) 0.145(7) 0.054(4) 0.021(4) -0.006(3) -0.014(4) C30 0.094(6) 0.084(6) 0.061(5) -0.021(4) 0.041(4) -0.019(5) C20 0.048(4) 0.106(7) 0.052(4) 0.017(4) -0.004(3) 0.000(4) C28 0.069(5) 0.098(7) 0.073(5) 0.001(5) 0.008(4) -0.019(5) C37 0.067(5) 0.071(5) 0.085(6) -0.010(4) 0.019(4) -0.008(4) C25 0.070(7) 0.201(15) 0.085(7) -0.040(8) 0.005(5) -0.029(9) C34 0.162(10) 0.069(6) 0.056(5) -0.017(4) 0.018(6) -0.019(6) C35 0.151(10) 0.095(8) 0.062(5) -0.011(5) 0.014(6) -0.038(7) C29 0.062(5) 0.123(9) 0.097(7) 0.020(6) 0.015(5) -0.011(6) C26 0.092(7) 0.140(11) 0.113(8) -0.049(7) 0.038(6) -0.050(7) C39 0.082(8) 0.247(18) 0.112(10) -0.018(10) 0.037(7) -0.030(9) C31 0.090(6) 0.073(6) 0.082(6) -0.018(5) 0.010(5) -0.015(5) C22 0.095(7) 0.134(9) 0.067(6) 0.036(6) -0.016(5) 0.012(6) C33 0.106(7) 0.065(6) 0.070(5) -0.001(4) 0.033(5) -0.001(5) C21 0.095(6) 0.103(7) 0.058(5) 0.004(4) -0.022(5) 0.023(5) C23 0.085(7) 0.247(17) 0.096(8) 0.072(9) 0.025(6) 0.027(8) C24 0.073(7) 0.166(12) 0.061(5) 0.003(6) 0.020(5) -0.015(7) C36 0.122(8) 0.103(8) 0.082(6) -0.028(6) 0.026(6) -0.004(7) C32 0.089(7) 0.101(8) 0.079(6) -0.017(5) 0.004(5) -0.002(6) C38 0.070(6) 0.195(13) 0.102(8) 0.006(8) 0.015(6) -0.049(7) O1W 0.043(2) 0.040(3) 0.111(4) 0.002(2) -0.028(2) -0.003(2) O2W 0.217(10) 0.111(7) 0.153(8) -0.036(5) -0.090(7) 0.053(6) O4W 0.46(2) 0.39(2) 0.240(16) -0.177(16) -0.121(17) 0.30(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 Ni1 N4 2.062(6) 4_544 ? Ni1 O1 2.069(4) . ? Ni1 O1W 2.081(4) . ? Ni1 O3 2.088(3) 8_465 ? Ni1 N1 2.092(6) . ? Ni1 N5 2.114(5) 5_665 ? O1 C19 1.251(8) . ? O3 C1 1.239(7) . ? O3 Ni1 2.088(3) 8_566 ? O2 C19 1.256(8) . ? O4 C1 1.241(7) . ? N5 C12 1.306(7) . ? N5 C8 1.330(6) . ? N5 Ni1 2.114(5) 5_665 ? C8 C9 1.381(8) . ? C8 H8 0.9300 . ? N1 C20 1.284(9) . ? N1 C21 1.355(9) . ? C2 C3 1.358(8) . ? C2 C7 1.373(8) . ? C2 C1 1.504(7) . ? C5 C6 1.362(8) . ? C5 C4 1.384(8) . ? C5 C9 1.480(7) . ? C9 C10 1.387(7) . ? C6 C7 1.382(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C14 C15 1.366(8) . ? C14 C13 1.390(8) . ? C14 H14 0.9300 . ? C10 C11 1.394(7) . ? C10 H10 0.9300 . ? C11 C12 1.374(8) . ? C11 C13 1.473(8) . ? C3 C4 1.376(8) . ? C3 H3 0.9300 . ? C13 C18 1.395(9) . ? C19 C16 1.500(9) . ? N4 C37 1.307(9) . ? N4 C38 1.314(11) . ? N4 Ni1 2.062(6) 4_554 ? C4 H4 0.9300 . ? N3 C39 1.288(14) . ? N3 C37 1.295(10) . ? N3 C36 1.482(11) . ? C12 H12 0.9300 . ? C16 C15 1.362(9) . ? C16 C17 1.410(9) . ? C18 C17 1.365(9) . ? C18 H18 0.9300 . ? C17 H17 0.9300 . ? C27 C28 1.343(12) . ? C27 C26 1.395(12) . ? C27 C30 1.480(13) . ? C15 H15 0.9300 . ? N2 C20 1.306(9) . ? N2 C22 1.363(12) . ? N2 C23 1.484(13) . ? C30 C35 1.352(13) . ? C30 C31 1.390(12) . ? C20 H20 0.9300 . ? C28 C29 1.364(12) . ? C28 H28 0.9300 . ? C37 H37 0.9300 . ? C25 C24 1.284(16) . ? C25 C26 1.494(17) . ? C25 H25 0.9300 . ? C34 C33 1.345(13) . ? C34 C35 1.361(15) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C29 C24 1.322(13) . ? C29 H29 0.9300 . ? C26 H26 0.9300 . ? C39 C38 1.366(16) . ? C39 H39 0.9300 . ? C31 C32 1.334(12) . ? C31 H31 0.9300 . ? C22 C21 1.301(13) . ? C22 H22 0.9300 . ? C33 C32 1.393(13) . ? C33 C36 1.477(14) . ? C21 H21 0.9300 . ? C23 C24 1.500(15) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C32 H32 0.9300 . ? C38 H38 0.9300 . ? O1W H1WA 0.9002 . ? O1W H1WB 0.9001 . ? O2W H2WA 0.8499 . ? O2W H2WB 0.8505 . ? O4W H4WA 0.8496 . ? O4W H4WB 0.8503 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni1 O1 90.1(2) 4_544 . ? N4 Ni1 O1W 90.3(2) 4_544 . ? O1 Ni1 O1W 86.90(16) . . ? N4 Ni1 O3 88.91(19) 4_544 8_465 ? O1 Ni1 O3 178.51(17) . 8_465 ? O1W Ni1 O3 92.02(16) . 8_465 ? N4 Ni1 N1 177.0(2) 4_544 . ? O1 Ni1 N1 90.2(2) . . ? O1W Ni1 N1 92.8(2) . . ? O3 Ni1 N1 90.88(19) 8_465 . ? N4 Ni1 N5 87.1(2) 4_544 5_665 ? O1 Ni1 N5 90.14(17) . 5_665 ? O1W Ni1 N5 176.05(19) . 5_665 ? O3 Ni1 N5 90.89(16) 8_465 5_665 ? N1 Ni1 N5 89.9(2) . 5_665 ? C19 O1 Ni1 126.3(5) . . ? C1 O3 Ni1 127.3(3) . 8_566 ? C12 N5 C8 117.6(5) . . ? C12 N5 Ni1 119.9(4) . 5_665 ? C8 N5 Ni1 122.4(4) . 5_665 ? N5 C8 C9 123.8(5) . . ? N5 C8 H8 118.1 . . ? C9 C8 H8 118.1 . . ? C20 N1 C21 105.4(7) . . ? C20 N1 Ni1 125.8(5) . . ? C21 N1 Ni1 128.2(6) . . ? C3 C2 C7 118.2(5) . . ? C3 C2 C1 120.1(5) . . ? C7 C2 C1 121.7(5) . . ? C6 C5 C4 118.3(5) . . ? C6 C5 C9 121.4(5) . . ? C4 C5 C9 120.3(5) . . ? C8 C9 C10 116.8(5) . . ? C8 C9 C5 119.6(5) . . ? C10 C9 C5 123.3(5) . . ? C5 C6 C7 120.9(5) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C2 C7 C6 120.7(5) . . ? C2 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C15 C14 C13 121.9(6) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 116.5(5) . . ? C12 C11 C13 119.9(5) . . ? C10 C11 C13 123.6(6) . . ? O3 C1 O4 125.8(5) . . ? O3 C1 C2 117.6(5) . . ? O4 C1 C2 116.6(5) . . ? C2 C3 C4 121.6(6) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C14 C13 C18 117.5(5) . . ? C14 C13 C11 120.4(6) . . ? C18 C13 C11 121.9(5) . . ? O2 C19 O1 126.5(6) . . ? O2 C19 C16 118.7(6) . . ? O1 C19 C16 114.9(6) . . ? C37 N4 C38 103.7(8) . . ? C37 N4 Ni1 130.8(5) . 4_554 ? C38 N4 Ni1 124.9(7) . 4_554 ? C3 C4 C5 120.2(6) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C39 N3 C37 107.4(8) . . ? C39 N3 C36 125.2(9) . . ? C37 N3 C36 126.8(8) . . ? N5 C12 C11 125.0(5) . . ? N5 C12 H12 117.5 . . ? C11 C12 H12 117.5 . . ? C15 C16 C17 118.4(6) . . ? C15 C16 C19 120.5(6) . . ? C17 C16 C19 120.9(6) . . ? C17 C18 C13 120.6(6) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C18 C17 C16 120.8(7) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C28 C27 C26 119.0(11) . . ? C28 C27 C30 122.2(8) . . ? C26 C27 C30 118.7(10) . . ? C16 C15 C14 120.8(6) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C20 N2 C22 106.1(8) . . ? C20 N2 C23 128.8(8) . . ? C22 N2 C23 125.0(8) . . ? C35 C30 C31 117.4(10) . . ? C35 C30 C27 119.9(10) . . ? C31 C30 C27 122.6(8) . . ? N1 C20 N2 112.2(7) . . ? N1 C20 H20 123.9 . . ? N2 C20 H20 123.9 . . ? C27 C28 C29 121.7(9) . . ? C27 C28 H28 119.1 . . ? C29 C28 H28 119.2 . . ? N3 C37 N4 112.9(7) . . ? N3 C37 H37 123.5 . . ? N4 C37 H37 123.6 . . ? C24 C25 C26 122.2(11) . . ? C24 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C33 C34 C35 120.7(9) . . ? C33 C34 H34 119.7 . . ? C35 C34 H34 119.6 . . ? C30 C35 C34 121.5(10) . . ? C30 C35 H35 119.2 . . ? C34 C35 H35 119.3 . . ? C24 C29 C28 122.2(11) . . ? C24 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C27 C26 C25 115.1(10) . . ? C27 C26 H26 122.4 . . ? C25 C26 H26 122.5 . . ? N3 C39 C38 106.4(9) . . ? N3 C39 H39 126.8 . . ? C38 C39 H39 126.8 . . ? C32 C31 C30 121.6(9) . . ? C32 C31 H31 119.2 . . ? C30 C31 H31 119.2 . . ? C21 C22 N2 106.7(8) . . ? C21 C22 H22 126.7 . . ? N2 C22 H22 126.6 . . ? C34 C33 C32 118.9(10) . . ? C34 C33 C36 121.5(9) . . ? C32 C33 C36 119.6(10) . . ? C22 C21 N1 109.6(8) . . ? C22 C21 H21 125.2 . . ? N1 C21 H21 125.2 . . ? N2 C23 C24 111.6(8) . . ? N2 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? N2 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C29 119.7(12) . . ? C25 C24 C23 117.5(12) . . ? C29 C24 C23 122.8(13) . . ? C33 C36 N3 117.1(8) . . ? C33 C36 H36A 108.1 . . ? N3 C36 H36A 108.0 . . ? C33 C36 H36B 108.0 . . ? N3 C36 H36B 108.0 . . ? H36A C36 H36B 107.3 . . ? C31 C32 C33 119.8(9) . . ? C31 C32 H32 120.1 . . ? C33 C32 H32 120.1 . . ? N4 C38 C39 109.4(10) . . ? N4 C38 H38 125.3 . . ? C39 C38 H38 125.3 . . ? Ni1 O1W H1WA 125.9 . . ? Ni1 O1W H1WB 125.8 . . ? H1WA O1W H1WB 108.3 . . ? H2WA O2W H2WB 109.5 . . ? H4WA O4W H4WB 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.816 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 932490' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H29 Co N5 O4' _chemical_formula_sum 'C39 H29 Co N5 O4' _chemical_formula_weight 690.60 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.6916(6) _cell_length_b 11.7881(6) _cell_length_c 12.6510(6) _cell_angle_alpha 82.0710(10) _cell_angle_beta 83.1130(10) _cell_angle_gamma 82.6380(10) _cell_volume 1703.38(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3469 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.35 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 714 _exptl_absorpt_coefficient_mu 0.552 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7852 _exptl_absorpt_correction_T_max 0.9317 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8848 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5952 _reflns_number_gt 4908 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+1.1132P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5952 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1518 _refine_ls_wR_factor_gt 0.1409 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 C1 C 0.8860(3) 0.6183(3) 0.4218(3) 0.0384(7) Uani 1 1 d . . . H1 H 0.9611 0.6033 0.4414 0.046 Uiso 1 1 calc R . . C2 C 0.7059(3) 0.6489(4) 0.4230(3) 0.0642(11) Uani 1 1 d . . . H2 H 0.6276 0.6596 0.4478 0.077 Uiso 1 1 calc R . . C3 C 0.7423(3) 0.6507(4) 0.3236(3) 0.0591(11) Uani 1 1 d . . . H3 H 0.6984 0.6628 0.2656 0.071 Uiso 1 1 calc R . . C4 C 0.9345(4) 0.6188(3) 0.2227(3) 0.0551(9) Uani 1 1 d . . . H4A H 0.9012 0.5716 0.1800 0.066 Uiso 1 1 calc R . . H4B H 1.0089 0.5790 0.2405 0.066 Uiso 1 1 calc R . . C5 C 0.9530(3) 0.7323(3) 0.1573(3) 0.0484(8) Uani 1 1 d . . . C6 C 1.0137(5) 0.8093(4) 0.1909(4) 0.0790(14) Uani 1 1 d . . . H6 H 1.0442 0.7906 0.2565 0.095 Uiso 1 1 calc R . . C7 C 1.0317(5) 0.9145(4) 0.1313(3) 0.0755(14) Uani 1 1 d . . . H7 H 1.0723 0.9653 0.1578 0.091 Uiso 1 1 calc R . . C8 C 0.9898(3) 0.9437(3) 0.0331(3) 0.0463(8) Uani 1 1 d . . . C9 C 0.9326(5) 0.8664(4) -0.0016(4) 0.0909(18) Uani 1 1 d . . . H9 H 0.9047 0.8830 -0.0685 0.109 Uiso 1 1 calc R . . C10 C 0.9143(5) 0.7622(4) 0.0602(4) 0.0933(18) Uani 1 1 d . . . H10 H 0.8738 0.7113 0.0336 0.112 Uiso 1 1 calc R . . C11 C 0.6995(4) 0.4436(4) 0.8839(3) 0.0709(13) Uani 1 1 d . . . H11 H 0.6547 0.4001 0.8529 0.085 Uiso 1 1 calc R . . C12 C 0.8053(6) 0.5584(6) 0.9070(4) 0.110(2) Uani 1 1 d . . . H12 H 0.8540 0.6165 0.8941 0.132 Uiso 1 1 calc R . . C13 C 0.7818(6) 0.5050(6) 1.0013(4) 0.113(2) Uani 1 1 d . . . H13 H 0.8072 0.5167 1.0655 0.135 Uiso 1 1 calc R . . C14 C 0.6646(8) 0.3544(6) 1.0779(4) 0.0463(8) Uani 1 1 d . . . H14A H 0.6020 0.3989 1.1170 0.171 Uiso 1 1 calc R . . H14B H 0.7242 0.3283 1.1257 0.171 Uiso 1 1 calc R . . C15 C 0.6192(7) 0.2511(6) 1.0478(4) 0.101(2) Uani 1 1 d . . . C16 C 0.6838(7) 0.1593(8) 1.0200(9) 0.174(4) Uani 1 1 d . . . H16 H 0.7638 0.1603 1.0101 0.208 Uiso 1 1 calc R . . C17 C 0.6394(6) 0.0609(6) 1.0046(9) 0.170(4) Uani 1 1 d . . . H17 H 0.6912 -0.0034 0.9907 0.205 Uiso 1 1 calc R . . C18 C 0.5239(4) 0.0525(4) 1.0085(4) 0.0754(13) Uani 1 1 d . . . C19 C 0.4567(6) 0.1497(6) 1.0382(6) 0.110(2) Uani 1 1 d . . . H19 H 0.3766 0.1501 1.0476 0.132 Uiso 1 1 calc R . . C20 C 0.5036(8) 0.2464(6) 1.0546(6) 0.124(2) Uani 1 1 d . . . H20 H 0.4537 0.3111 1.0710 0.149 Uiso 1 1 calc R . . C21 C 0.6672(3) 0.8353(3) 0.6607(3) 0.0390(7) Uani 1 1 d . . . H21 H 0.7442 0.8459 0.6635 0.047 Uiso 1 1 calc R . . C22 C 0.5873(2) 0.9314(2) 0.6503(3) 0.0345(7) Uani 1 1 d . . . C23 C 0.4728(3) 0.9135(2) 0.6461(3) 0.0382(7) Uani 1 1 d . . . H23 H 0.4168 0.9765 0.6363 0.046 Uiso 1 1 calc R . . C24 C 0.4409(2) 0.8028(2) 0.6564(2) 0.0324(6) Uani 1 1 d . . . C25 C 0.5293(2) 0.7121(2) 0.6656(2) 0.0323(6) Uani 1 1 d . . . H25 H 0.5101 0.6372 0.6710 0.039 Uiso 1 1 calc R . . C26 C 0.3186(3) 0.7805(3) 0.6617(3) 0.0352(7) Uani 1 1 d . . . C27 C 0.2880(3) 0.6813(3) 0.6306(3) 0.0373(7) Uani 1 1 d . . . H27 H 0.3455 0.6279 0.6032 0.045 Uiso 1 1 calc R . . C28 C 0.1731(3) 0.6605(3) 0.6400(3) 0.0408(7) Uani 1 1 d . . . H28 H 0.1542 0.5945 0.6166 0.049 Uiso 1 1 calc R . . C29 C 0.0865(3) 0.7364(3) 0.6835(3) 0.0414(8) Uani 1 1 d . . . C30 C 0.1161(3) 0.8366(3) 0.7122(4) 0.0640(12) Uani 1 1 d . . . H30 H 0.0585 0.8900 0.7394 0.077 Uiso 1 1 calc R . . C31 C 0.2305(3) 0.8584(3) 0.7010(4) 0.0588(11) Uani 1 1 d . . . H31 H 0.2486 0.9268 0.7203 0.071 Uiso 1 1 calc R . . C32 C -0.0390(3) 0.7125(3) 0.7019(3) 0.0452(8) Uani 1 1 d . . . C33 C 0.6231(3) 1.0486(2) 0.6460(3) 0.0372(7) Uani 1 1 d . . . C34 C 0.5459(3) 1.1393(3) 0.6771(4) 0.0576(11) Uani 1 1 d . . . H34 H 0.4696 1.1269 0.7010 0.069 Uiso 1 1 calc R . . C35 C 0.5792(3) 1.2483(3) 0.6737(4) 0.0543(10) Uani 1 1 d . . . H35 H 0.5247 1.3084 0.6935 0.065 Uiso 1 1 calc R . . C36 C 0.6918(3) 1.2685(2) 0.6414(3) 0.0352(7) Uani 1 1 d . . . C37 C 0.7709(3) 1.1783(3) 0.6112(3) 0.0458(8) Uani 1 1 d . . . H37 H 0.8477 1.1904 0.5899 0.055 Uiso 1 1 calc R . . C38 C 0.7368(3) 1.0703(3) 0.6122(3) 0.0468(9) Uani 1 1 d . . . H38 H 0.7908 1.0110 0.5898 0.056 Uiso 1 1 calc R . . C39 C 0.7272(3) 1.3866(2) 0.6397(2) 0.0347(7) Uani 1 1 d . . . Co1 Co 0.77399(3) 0.58563(3) 0.66034(3) 0.03032(16) Uani 1 1 d . . . N1 N 0.7912(2) 0.6300(2) 0.4892(2) 0.0408(6) Uani 1 1 d . . . N2 N 0.8582(3) 0.6312(2) 0.3217(2) 0.0468(7) Uani 1 1 d . . . N3 N 0.7559(3) 0.5254(2) 0.8302(2) 0.0459(7) Uani 1 1 d . . . N4 N 0.7131(4) 0.4296(3) 0.9857(3) 0.0785(12) Uani 1 1 d . . . N5 N 0.6401(2) 0.7274(2) 0.6672(2) 0.0351(6) Uani 1 1 d . . . O1 O -0.06496(19) 0.6308(2) 0.6588(2) 0.0484(6) Uani 1 1 d . . . O2 O -0.1077(2) 0.7743(2) 0.7577(2) 0.0632(7) Uani 1 1 d . . . O3 O 0.64961(19) 1.46924(17) 0.6500(2) 0.0437(6) Uani 1 1 d . . . O4 O 0.83311(18) 1.40067(18) 0.63122(19) 0.0415(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0362(17) 0.0295(16) 0.0486(19) 0.0012(13) -0.0043(14) -0.0071(13) C2 0.0321(19) 0.095(3) 0.061(3) 0.004(2) -0.0109(17) 0.0024(19) C3 0.039(2) 0.094(3) 0.040(2) 0.0059(19) -0.0163(16) 0.0044(19) C4 0.072(3) 0.046(2) 0.043(2) 0.0004(16) -0.0007(18) -0.0014(18) C5 0.058(2) 0.0437(19) 0.0394(18) 0.0013(15) -0.0020(16) -0.0013(16) C6 0.115(4) 0.071(3) 0.054(3) 0.017(2) -0.036(3) -0.025(3) C7 0.112(4) 0.061(3) 0.060(3) 0.014(2) -0.034(3) -0.031(3) C8 0.054(2) 0.045(2) 0.0365(18) 0.0033(15) -0.0035(15) -0.0017(16) C9 0.152(5) 0.079(3) 0.053(3) 0.021(2) -0.049(3) -0.053(3) C10 0.154(5) 0.076(3) 0.064(3) 0.015(2) -0.043(3) -0.060(3) C11 0.097(3) 0.073(3) 0.050(2) -0.005(2) 0.002(2) -0.051(3) C12 0.159(6) 0.136(5) 0.056(3) -0.002(3) -0.012(3) -0.106(5) C13 0.180(6) 0.142(5) 0.037(2) 0.008(3) -0.020(3) -0.114(5) C14 0.054(2) 0.045(2) 0.0365(18) 0.0033(15) -0.0035(15) -0.0017(16) C15 0.153(6) 0.092(4) 0.060(3) 0.010(3) 0.013(3) -0.060(4) C16 0.101(5) 0.137(7) 0.289(13) -0.077(8) 0.059(6) -0.058(5) C17 0.089(5) 0.099(5) 0.324(13) -0.082(7) 0.056(6) -0.025(4) C18 0.076(3) 0.064(3) 0.078(3) 0.002(2) 0.018(2) -0.012(2) C19 0.091(4) 0.098(5) 0.144(6) -0.028(4) -0.020(4) -0.002(4) C20 0.156(7) 0.074(4) 0.145(6) -0.027(4) -0.030(5) 0.003(4) C21 0.0254(15) 0.0261(15) 0.067(2) -0.0062(14) -0.0079(14) -0.0070(12) C22 0.0280(15) 0.0207(14) 0.0568(19) -0.0066(13) -0.0059(13) -0.0072(11) C23 0.0290(16) 0.0229(15) 0.063(2) -0.0055(14) -0.0070(14) -0.0032(12) C24 0.0278(15) 0.0270(15) 0.0451(17) -0.0088(13) -0.0030(12) -0.0091(12) C25 0.0284(15) 0.0239(14) 0.0463(17) -0.0068(12) -0.0013(12) -0.0096(12) C26 0.0284(15) 0.0291(15) 0.0504(18) -0.0048(13) -0.0072(13) -0.0094(12) C27 0.0287(15) 0.0295(15) 0.056(2) -0.0104(14) -0.0048(13) -0.0081(12) C28 0.0371(17) 0.0337(17) 0.056(2) -0.0062(14) -0.0085(14) -0.0164(14) C29 0.0300(16) 0.0380(17) 0.059(2) -0.0032(15) -0.0092(14) -0.0119(13) C30 0.0301(18) 0.048(2) 0.120(4) -0.031(2) -0.003(2) -0.0066(16) C31 0.0322(18) 0.0395(19) 0.113(3) -0.033(2) -0.0043(19) -0.0118(15) C32 0.0342(18) 0.046(2) 0.057(2) 0.0045(16) -0.0124(16) -0.0146(15) C33 0.0296(15) 0.0237(15) 0.060(2) -0.0035(13) -0.0097(14) -0.0073(12) C34 0.0278(17) 0.0285(17) 0.119(3) -0.0162(19) -0.0023(18) -0.0101(14) C35 0.0342(18) 0.0236(16) 0.107(3) -0.0163(18) -0.0038(18) -0.0031(13) C36 0.0346(16) 0.0256(15) 0.0475(18) -0.0041(13) -0.0065(13) -0.0103(12) C37 0.0313(17) 0.0310(17) 0.076(2) -0.0091(16) -0.0002(16) -0.0098(13) C38 0.0323(17) 0.0239(15) 0.085(3) -0.0127(16) -0.0028(16) -0.0037(13) C39 0.0406(18) 0.0242(15) 0.0414(17) -0.0033(12) -0.0092(13) -0.0083(13) Co1 0.0239(2) 0.0199(2) 0.0479(3) -0.00361(16) -0.00264(17) -0.00700(15) N1 0.0345(14) 0.0397(15) 0.0464(16) 0.0038(12) -0.0065(12) -0.0052(11) N2 0.0512(18) 0.0415(16) 0.0447(17) 0.0055(12) -0.0059(13) -0.0050(13) N3 0.0518(17) 0.0398(15) 0.0465(16) -0.0045(12) 0.0010(13) -0.0135(13) N4 0.119(3) 0.075(2) 0.044(2) 0.0016(17) 0.004(2) -0.042(2) N5 0.0265(13) 0.0208(12) 0.0588(17) -0.0047(11) -0.0031(11) -0.0065(10) O1 0.0358(12) 0.0514(14) 0.0625(15) -0.0011(12) -0.0101(11) -0.0242(11) O2 0.0306(13) 0.0709(18) 0.091(2) -0.0176(16) -0.0058(13) -0.0084(12) O3 0.0400(12) 0.0217(11) 0.0712(16) -0.0066(10) -0.0080(11) -0.0080(9) O4 0.0377(12) 0.0295(11) 0.0607(14) -0.0078(10) -0.0053(10) -0.0150(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.328(4) . ? C1 N1 1.320(4) . ? C1 H1 0.9300 . ? C2 C3 1.276(5) . ? C2 N1 1.356(4) . ? C2 H2 0.9300 . ? C3 N2 1.343(4) . ? C3 H3 0.9300 . ? C4 N2 1.460(5) . ? C4 C5 1.500(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.361(6) . ? C5 C10 1.345(6) . ? C6 C7 1.386(6) . ? C6 H6 0.9300 . ? C7 C8 1.373(5) . ? C7 H7 0.9300 . ? C8 C9 1.345(6) . ? C8 C8 1.499(7) 2_775 ? C9 C10 1.388(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 N3 1.304(5) . ? C11 N4 1.301(5) . ? C11 H11 0.9300 . ? C12 C13 1.286(7) . ? C12 N3 1.314(5) . ? C12 H12 0.9300 . ? C13 N4 1.320(6) . ? C13 H13 0.9300 . ? C14 N4 1.468(6) . ? C14 C15 1.501(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.303(10) . ? C15 C20 1.352(9) . ? C16 C17 1.376(10) . ? C16 H16 0.9300 . ? C17 C18 1.361(9) . ? C17 H17 0.9300 . ? C18 C19 1.374(8) . ? C18 C18 1.474(10) 2_657 ? C19 C20 1.377(9) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N5 1.339(4) . ? C21 C22 1.375(4) . ? C21 H21 0.9300 . ? C22 C23 1.390(4) . ? C22 C33 1.486(4) . ? C23 C24 1.387(4) . ? C23 H23 0.9300 . ? C24 C25 1.391(4) . ? C24 C26 1.480(4) . ? C25 N5 1.334(4) . ? C25 H25 0.9300 . ? C26 C27 1.385(4) . ? C26 C31 1.383(5) . ? C27 C28 1.384(4) . ? C27 H27 0.9300 . ? C28 C29 1.378(5) . ? C28 H28 0.9300 . ? C29 C30 1.379(5) . ? C29 C32 1.514(4) . ? C30 C31 1.381(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 O2 1.237(4) . ? C32 O1 1.255(4) . ? C33 C34 1.377(5) . ? C33 C38 1.392(4) . ? C34 C35 1.383(4) . ? C34 H34 0.9300 . ? C35 C36 1.372(4) . ? C35 H35 0.9300 . ? C36 C37 1.381(4) . ? C36 C39 1.498(4) . ? C37 C38 1.380(4) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 O4 1.260(4) . ? C39 O3 1.253(4) . ? Co1 O1 2.018(2) 1_655 ? Co1 N5 2.142(2) . ? Co1 N1 2.147(3) . ? Co1 O3 2.150(2) 1_545 ? Co1 N3 2.163(3) . ? Co1 O4 2.268(2) 1_545 ? O1 Co1 2.018(2) 1_455 ? O3 Co1 2.150(2) 1_565 ? O4 Co1 2.268(2) 1_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 110.0(3) . . ? N2 C1 H1 125.0 . . ? N1 C1 H1 125.0 . . ? C3 C2 N1 114.2(3) . . ? C3 C2 H2 122.9 . . ? N1 C2 H2 122.9 . . ? C2 C3 N2 104.5(3) . . ? C2 C3 H3 127.8 . . ? N2 C3 H3 127.8 . . ? N2 C4 C5 112.8(3) . . ? N2 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N2 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C10 116.1(4) . . ? C6 C5 C4 121.9(3) . . ? C10 C5 C4 122.0(4) . . ? C5 C6 C7 122.6(4) . . ? C5 C6 H6 118.7 . . ? C7 C6 H6 118.7 . . ? C8 C7 C6 120.2(4) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 117.3(4) . . ? C9 C8 C8 121.8(4) . 2_775 ? C7 C8 C8 120.8(4) . 2_775 ? C8 C9 C10 121.5(4) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C5 C10 C9 122.4(4) . . ? C5 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N3 C11 N4 112.4(4) . . ? N3 C11 H11 123.8 . . ? N4 C11 H11 123.8 . . ? C13 C12 N3 115.4(4) . . ? C13 C12 H12 122.3 . . ? N3 C12 H12 122.3 . . ? C12 C13 N4 103.7(4) . . ? C12 C13 H13 128.1 . . ? N4 C13 H13 128.1 . . ? N4 C14 C15 113.8(4) . . ? N4 C14 H14A 108.8 . . ? C15 C14 H14A 108.8 . . ? N4 C14 H14B 108.8 . . ? C15 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C20 115.4(7) . . ? C16 C15 C14 124.6(8) . . ? C20 C15 C14 119.9(8) . . ? C15 C16 C17 123.2(7) . . ? C15 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C18 C17 C16 123.6(7) . . ? C18 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C17 C18 C19 112.5(6) . . ? C17 C18 C18 123.8(6) . 2_657 ? C19 C18 C18 123.6(6) . 2_657 ? C18 C19 C20 122.5(6) . . ? C18 C19 H19 118.7 . . ? C20 C19 H19 118.8 . . ? C15 C20 C19 122.6(7) . . ? C15 C20 H20 118.7 . . ? C19 C20 H20 118.7 . . ? N5 C21 C22 123.6(3) . . ? N5 C21 H21 118.2 . . ? C22 C21 H21 118.2 . . ? C21 C22 C23 117.1(3) . . ? C21 C22 C33 120.7(3) . . ? C23 C22 C33 122.2(3) . . ? C22 C23 C24 120.8(3) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C25 117.0(3) . . ? C23 C24 C26 122.2(3) . . ? C25 C24 C26 120.7(3) . . ? N5 C25 C24 123.1(3) . . ? N5 C25 H25 118.4 . . ? C24 C25 H25 118.4 . . ? C27 C26 C31 117.7(3) . . ? C27 C26 C24 122.1(3) . . ? C31 C26 C24 120.2(3) . . ? C28 C27 C26 121.0(3) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C29 C28 C27 120.8(3) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 118.5(3) . . ? C28 C29 C32 122.2(3) . . ? C30 C29 C32 119.3(3) . . ? C29 C30 C31 120.7(3) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C26 C31 C30 121.3(3) . . ? C26 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? O2 C32 O1 125.2(3) . . ? O2 C32 C29 118.0(3) . . ? O1 C32 C29 116.9(3) . . ? C34 C33 C38 117.4(3) . . ? C34 C33 C22 121.4(3) . . ? C38 C33 C22 121.1(3) . . ? C33 C34 C35 121.5(3) . . ? C33 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? C36 C35 C34 120.6(3) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C37 118.7(3) . . ? C35 C36 C39 120.1(3) . . ? C37 C36 C39 121.2(3) . . ? C36 C37 C38 120.6(3) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C33 C38 C37 121.1(3) . . ? C33 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? O4 C39 O3 121.3(3) . . ? O4 C39 C36 120.1(3) . . ? O3 C39 C36 118.6(3) . . ? O1 Co1 N5 113.70(10) 1_655 . ? O1 Co1 N1 87.49(10) 1_655 . ? N5 Co1 N1 87.19(10) . . ? O1 Co1 O3 154.87(10) 1_655 1_545 ? N5 Co1 O3 91.26(9) . 1_545 ? N1 Co1 O3 91.06(10) . 1_545 ? O1 Co1 N3 94.69(10) 1_655 . ? N5 Co1 N3 96.06(11) . . ? N1 Co1 N3 174.95(10) . . ? O3 Co1 N3 85.03(10) 1_545 . ? O1 Co1 O4 95.48(9) 1_655 1_545 ? N5 Co1 O4 150.02(9) . 1_545 ? N1 Co1 O4 87.39(9) . 1_545 ? O3 Co1 O4 59.39(8) 1_545 1_545 ? N3 Co1 O4 87.87(10) . 1_545 ? C1 N1 C2 102.6(3) . . ? C1 N1 Co1 127.9(2) . . ? C2 N1 Co1 127.7(2) . . ? C1 N2 C3 108.7(3) . . ? C1 N2 C4 128.6(3) . . ? C3 N2 C4 122.5(3) . . ? C11 N3 C12 100.9(4) . . ? C11 N3 Co1 130.4(3) . . ? C12 N3 Co1 128.6(3) . . ? C11 N4 C13 107.6(4) . . ? C11 N4 C14 133.0(4) . . ? C13 N4 C14 119.4(4) . . ? C25 N5 C21 118.3(2) . . ? C25 N5 Co1 120.90(19) . . ? C21 N5 Co1 120.40(19) . . ? C32 O1 Co1 125.9(2) . 1_455 ? C39 O3 Co1 92.29(18) . 1_565 ? C39 O4 Co1 86.76(17) . 1_565 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.906 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 932485' ####################################################################### # # 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 'C14 H12 Mn N O6' _chemical_formula_sum 'C14 H12 Mn N O6' _chemical_formula_weight 345.19 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.768(5) _cell_length_b 10.017(3) _cell_length_c 16.158(4) _cell_angle_alpha 90.00 _cell_angle_beta 121.098(4) _cell_angle_gamma 90.00 _cell_volume 2878.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3170 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7093 _exptl_absorpt_correction_T_max 0.8048 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _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 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7094 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2538 _reflns_number_gt 2217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+7.4450P] 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 2538 _refine_ls_number_parameters 205 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1914 _refine_ls_wR_factor_gt 0.1850 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 1.000 _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 Mn1 Mn 0.14083(3) 0.45526(5) 0.36876(4) 0.03205(17) Uani 1 1 d D . . N1 N -0.25534(15) -0.0418(3) 0.3587(2) 0.0326(7) Uani 1 1 d . . . O1 O 0.16013(13) 0.1962(3) 0.3808(2) 0.0457(7) Uani 1 1 d . . . O2 O 0.06493(13) 0.3047(2) 0.3696(2) 0.0474(7) Uani 1 1 d . . . O3 O 0.14233(14) -0.3089(3) 0.3555(2) 0.0555(8) Uani 1 1 d . . . O4 O 0.06130(14) -0.4069(3) 0.3818(2) 0.0519(8) Uani 1 1 d . . . O5 O 0.21538(17) 0.4547(3) 0.5255(2) 0.0516(8) Uani 1 1 d . . . C3 C 0.2075(4) 0.5188(8) 0.5953(5) 0.109(3) Uani 1 1 d . . . H3A H 0.2501 0.4991 0.6579 0.164 Uiso 1 1 calc R . . H3B H 0.1624 0.4886 0.5920 0.164 Uiso 1 1 calc R . . H3C H 0.2045 0.6134 0.5844 0.164 Uiso 1 1 calc R . . C8 C 0.06002(17) 0.0696(3) 0.3740(2) 0.0279(7) Uani 1 1 d . . . C16 C 0.05598(16) -0.1700(3) 0.3711(2) 0.0286(7) Uani 1 1 d . . . C18 C -0.04423(17) -0.0453(3) 0.3693(2) 0.0261(7) Uani 1 1 d . . . O1W O 0.07191(7) 0.4368(2) 0.20884(14) 0.0627(10) Uani 1 1 d D . . C23 C -0.00720(17) 0.0717(3) 0.3722(2) 0.0275(7) Uani 1 1 d . . . H23A H -0.0282 0.1534 0.3729 0.033 Uiso 1 1 calc R . . C24 C -0.01114(16) -0.1658(3) 0.3704(2) 0.0290(7) Uani 1 1 d . . . H24A H -0.0342 -0.2452 0.3707 0.035 Uiso 1 1 calc R . . C27 C 0.09804(17) 0.1973(3) 0.3756(2) 0.0326(8) Uani 1 1 d . . . C28 C -0.14423(19) 0.0691(4) 0.3870(3) 0.0416(9) Uani 1 1 d . . . H28A H -0.1159 0.1471 0.4056 0.050 Uiso 1 1 calc R . . C30 C 0.09117(18) -0.0524(3) 0.3721(2) 0.0283(8) Uani 1 1 d . . . H30A H 0.1357 -0.0549 0.3715 0.034 Uiso 1 1 calc R . . C31 C -0.11769(18) -0.0426(3) 0.3638(2) 0.0278(7) Uani 1 1 d . . . C35 C 0.08908(18) -0.3029(4) 0.3692(3) 0.0356(8) Uani 1 1 d . . . C37 C -0.2119(2) 0.0661(4) 0.3827(3) 0.0435(10) Uani 1 1 d . . . H37A H -0.2284 0.1439 0.3973 0.052 Uiso 1 1 calc R . . C39 C -0.1648(2) -0.1523(4) 0.3345(4) 0.0582(11) Uani 1 1 d . . . H39A H -0.1513 -0.2296 0.3152 0.070 Uiso 1 1 calc R . . C44 C -0.2312(2) -0.1488(4) 0.3336(4) 0.0546(11) Uani 1 1 d . . . H44A H -0.2609 -0.2251 0.3144 0.066 Uiso 1 1 calc R . . H1W H 0.08335(10) 0.4888(4) 0.1790(3) 0.080 Uiso 1 1 d D . . H2W H 0.02858(12) 0.4084(5) 0.1766(3) 0.080 Uiso 1 1 d 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 Mn1 0.0236(2) 0.0241(3) 0.0560(3) 0.00026(19) 0.0259(2) 0.00060(17) N1 0.0235(11) 0.0286(15) 0.0533(15) -0.0009(11) 0.0253(11) -0.0007(10) O1 0.0309(9) 0.0377(14) 0.0788(15) 0.0079(12) 0.0356(10) -0.0030(11) O2 0.0346(11) 0.0190(12) 0.0895(17) 0.0077(11) 0.0328(12) 0.0011(10) O3 0.0477(12) 0.0340(15) 0.1057(19) 0.0048(13) 0.0545(12) 0.0124(11) O4 0.0439(12) 0.0211(12) 0.0996(19) 0.0008(13) 0.0432(13) 0.0009(11) O5 0.0413(14) 0.0594(19) 0.0528(14) -0.0031(12) 0.0234(12) 0.0110(12) C3 0.111(5) 0.129(6) 0.090(4) 0.001(4) 0.054(4) 0.047(4) C8 0.0224(13) 0.0229(15) 0.0391(15) 0.0042(12) 0.0164(12) 0.0019(12) C16 0.0246(12) 0.0215(16) 0.0428(15) 0.0015(12) 0.0196(11) 0.0041(12) C18 0.0216(13) 0.0254(17) 0.0357(14) -0.0001(11) 0.0180(11) -0.0004(11) O1W 0.0386(14) 0.087(2) 0.0594(16) 0.0006(15) 0.0234(13) -0.0127(14) C23 0.0248(13) 0.0197(14) 0.0427(15) 0.0040(12) 0.0207(12) 0.0031(12) C24 0.0254(13) 0.0223(16) 0.0431(15) -0.0017(12) 0.0204(11) -0.0033(12) C27 0.0237(13) 0.0255(17) 0.0495(17) 0.0063(13) 0.0195(12) -0.0019(13) C28 0.0317(15) 0.0278(18) 0.076(2) -0.0108(16) 0.0356(15) -0.0059(14) C30 0.0207(13) 0.0259(17) 0.0445(15) 0.0026(12) 0.0211(12) 0.0028(11) C31 0.0247(13) 0.0258(17) 0.0402(15) 0.0024(11) 0.0219(11) 0.0012(11) C35 0.0257(13) 0.0274(17) 0.0542(18) -0.0008(14) 0.0211(13) 0.0041(13) C37 0.0349(16) 0.0311(18) 0.075(2) -0.0092(16) 0.0358(16) 0.0008(14) C39 0.0500(16) 0.031(2) 0.122(3) -0.0129(19) 0.0639(18) -0.0064(16) C44 0.0446(16) 0.0308(19) 0.111(3) -0.0082(19) 0.0561(17) -0.0076(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O5 2.182(3) . ? Mn1 O2 2.186(3) . ? Mn1 O1W 2.223(2) . ? Mn1 N1 2.245(3) 3 ? Mn1 O4 2.244(3) 1_565 ? Mn1 O3 2.374(3) 1_565 ? N1 C37 1.331(5) . ? N1 C44 1.332(5) . ? N1 Mn1 2.245(3) 3_445 ? O1 C27 1.248(4) . ? O2 C27 1.254(4) . ? O3 C35 1.236(5) . ? O3 Mn1 2.374(3) 1_545 ? O4 C35 1.257(5) . ? O4 Mn1 2.244(3) 1_545 ? O5 C3 1.379(8) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C8 C23 1.382(5) . ? C8 C30 1.390(5) . ? C8 C27 1.497(5) . ? C16 C30 1.382(5) . ? C16 C24 1.389(5) . ? C16 C35 1.506(5) . ? C18 C24 1.385(4) . ? C18 C23 1.390(4) . ? C18 C31 1.482(5) . ? O1W H1W 0.8241(12) . ? O1W H2W 0.8234(12) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C28 C37 1.371(6) . ? C28 C31 1.382(5) . ? C28 H28A 0.9300 . ? C30 H30A 0.9300 . ? C31 C39 1.382(5) . ? C37 H37A 0.9300 . ? C39 C44 1.372(6) . ? C39 H39A 0.9300 . ? C44 H44A 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 O5 Mn1 O2 94.19(12) . . ? O5 Mn1 O1W 173.78(10) . . ? O2 Mn1 O1W 85.19(10) . . ? O5 Mn1 N1 87.23(12) . 3 ? O2 Mn1 N1 137.05(10) . 3 ? O1W Mn1 N1 89.01(9) . 3 ? O5 Mn1 O4 90.47(12) . 1_565 ? O2 Mn1 O4 81.72(11) . 1_565 ? O1W Mn1 O4 95.56(10) . 1_565 ? N1 Mn1 O4 141.22(10) 3 1_565 ? O5 Mn1 O3 94.17(11) . 1_565 ? O2 Mn1 O3 136.90(10) . 1_565 ? O1W Mn1 O3 90.48(10) . 1_565 ? N1 Mn1 O3 85.55(10) 3 1_565 ? O4 Mn1 O3 56.00(10) 1_565 1_565 ? C37 N1 C44 115.9(3) . . ? C37 N1 Mn1 121.5(2) . 3_445 ? C44 N1 Mn1 122.6(2) . 3_445 ? C27 O2 Mn1 103.0(2) . . ? C35 O3 Mn1 88.7(2) . 1_545 ? C35 O4 Mn1 94.2(2) . 1_545 ? C3 O5 Mn1 129.4(3) . . ? O5 C3 H3A 109.5 . . ? O5 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? O5 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C23 C8 C30 119.3(3) . . ? C23 C8 C27 120.3(3) . . ? C30 C8 C27 120.3(3) . . ? C30 C16 C24 119.8(3) . . ? C30 C16 C35 120.6(3) . . ? C24 C16 C35 119.6(3) . . ? C24 C18 C23 118.2(3) . . ? C24 C18 C31 120.4(3) . . ? C23 C18 C31 121.4(3) . . ? Mn1 O1W H1W 114.9(3) . . ? Mn1 O1W H2W 127.0(4) . . ? H1W O1W H2W 113.6(2) . . ? C8 C23 C18 121.5(3) . . ? C8 C23 H23A 119.2 . . ? C18 C23 H23A 119.2 . . ? C18 C24 C16 121.1(3) . . ? C18 C24 H24A 119.5 . . ? C16 C24 H24A 119.5 . . ? O1 C27 O2 121.3(3) . . ? O1 C27 C8 120.7(3) . . ? O2 C27 C8 118.0(3) . . ? C37 C28 C31 120.7(3) . . ? C37 C28 H28A 119.7 . . ? C31 C28 H28A 119.7 . . ? C16 C30 C8 120.0(3) . . ? C16 C30 H30A 120.0 . . ? C8 C30 H30A 120.0 . . ? C28 C31 C39 115.2(3) . . ? C28 C31 C18 122.7(3) . . ? C39 C31 C18 122.0(3) . . ? O3 C35 O4 121.1(3) . . ? O3 C35 C16 120.4(3) . . ? O4 C35 C16 118.5(3) . . ? N1 C37 C28 123.8(4) . . ? N1 C37 H37A 118.1 . . ? C28 C37 H37A 118.1 . . ? C44 C39 C31 120.8(4) . . ? C44 C39 H39A 119.6 . . ? C31 C39 H39A 119.6 . . ? N1 C44 C39 123.5(4) . . ? N1 C44 H44A 118.2 . . ? C39 C44 H44A 118.2 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.663 _refine_diff_density_min -0.703 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 949697' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N3 Ni O7' _chemical_formula_weight 497.12 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.241(6) _cell_length_b 15.950(6) _cell_length_c 16.740(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.386(7) _cell_angle_gamma 90.00 _cell_volume 4368(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1037 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 20.34 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas colorless _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 0.938 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7170 _exptl_absorpt_correction_T_max 0.8721 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _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 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13599 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.1438 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.22 _reflns_number_total 5255 _reflns_number_gt 2608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^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 5255 _refine_ls_number_parameters 322 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1541 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1829 _refine_ls_wR_factor_gt 0.1448 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.999 _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 C1 C 0.3871(3) 0.2798(3) 0.3054(3) 0.0306(11) Uani 1 1 d . . . C2 C 0.4303(3) 0.3115(3) 0.3927(3) 0.0276(10) Uani 1 1 d . . . C3 C 0.5048(3) 0.2795(3) 0.4394(3) 0.0285(11) Uani 1 1 d . . . H3 H 0.5298 0.2391 0.4159 0.034 Uiso 1 1 calc R . . C4 C 0.5434(3) 0.3065(3) 0.5211(3) 0.0272(10) Uani 1 1 d . . . C5 C 0.5071(3) 0.3692(3) 0.5550(3) 0.0326(12) Uani 1 1 d . . . H5 H 0.5328 0.3875 0.6098 0.039 Uiso 1 1 calc R . . C6 C 0.4330(3) 0.4048(3) 0.5084(3) 0.0295(11) Uani 1 1 d . . . C7 C 0.3955(3) 0.3740(3) 0.4274(3) 0.0306(11) Uani 1 1 d . . . H7 H 0.3454 0.3963 0.3957 0.037 Uiso 1 1 calc R . . C8 C 0.6219(3) 0.2644(3) 0.5711(3) 0.0282(11) Uani 1 1 d . . . C9 C 0.3939(3) 0.4733(3) 0.5430(3) 0.0316(11) Uani 1 1 d . . . C10 C 0.3179(4) 0.5022(5) 0.5009(4) 0.094(3) Uani 1 1 d . . . H10 H 0.2894 0.4786 0.4491 0.113 Uiso 1 1 calc R . . C11 C 0.2822(4) 0.5648(4) 0.5326(4) 0.079(2) Uani 1 1 d . . . H11 H 0.2308 0.5830 0.4997 0.095 Uiso 1 1 calc R . . C12 C 0.3887(4) 0.5730(4) 0.6459(4) 0.0594(18) Uani 1 1 d . . . H12 H 0.4157 0.5975 0.6977 0.071 Uiso 1 1 calc R . . C13 C 0.4284(3) 0.5113(4) 0.6181(3) 0.0564(17) Uani 1 1 d . . . H13 H 0.4804 0.4950 0.6513 0.068 Uiso 1 1 calc R . . C14 C 0.2066(4) 0.4906(4) 0.1965(5) 0.071(2) Uani 1 1 d . . . H14 H 0.2367 0.5181 0.1671 0.086 Uiso 1 1 calc R . . C15 C 0.1771(5) 0.5271(4) 0.2542(5) 0.083(3) Uani 1 1 d . . . H15 H 0.1834 0.5827 0.2718 0.100 Uiso 1 1 calc R . . C16 C 0.1449(3) 0.3964(3) 0.2404(3) 0.0373(12) Uani 1 1 d . . . H16 H 0.1237 0.3446 0.2486 0.045 Uiso 1 1 calc R . . C17 C 0.0965(3) 0.4747(3) 0.3438(3) 0.0415(13) Uani 1 1 d . . . C18 C 0.0957(5) 0.4118(4) 0.3968(5) 0.088(3) Uani 1 1 d . . . H18 H 0.1211 0.3612 0.3926 0.106 Uiso 1 1 calc R . . C19 C 0.0573(5) 0.4215(4) 0.4580(4) 0.097(3) Uani 1 1 d . . . H19 H 0.0572 0.3769 0.4937 0.116 Uiso 1 1 calc R . . C20 C 0.0202(3) 0.4942(3) 0.4670(3) 0.0443(14) Uani 1 1 d . . . C21 C 0.0199(5) 0.5555(4) 0.4106(5) 0.074(2) Uani 1 1 d . . . H21 H -0.0073 0.6053 0.4130 0.088 Uiso 1 1 calc R . . C22 C 0.0578(5) 0.5472(4) 0.3505(4) 0.068(2) Uani 1 1 d . . . H22 H 0.0570 0.5914 0.3141 0.082 Uiso 1 1 calc R . . N1 N 0.3142(2) 0.6008(2) 0.6046(2) 0.0314(9) Uani 1 1 d . . . N2 N 0.1860(2) 0.4085(2) 0.1880(2) 0.0326(10) Uani 1 1 d . . . N3 N 0.1365(3) 0.4659(3) 0.2809(3) 0.0422(11) Uani 1 1 d . . . Ni1 Ni 0.24760(4) 0.31315(4) 0.14850(4) 0.0288(2) Uani 1 1 d . . . O1 O 0.3173(2) 0.3110(2) 0.27022(19) 0.0436(9) Uani 1 1 d . . . O2 O 0.4212(3) 0.2276(3) 0.2738(2) 0.0607(12) Uani 1 1 d . . . O3 O 0.6567(2) 0.2148(2) 0.53413(18) 0.0342(8) Uani 1 1 d . . . O4 O 0.6515(2) 0.2768(2) 0.64935(19) 0.0357(8) Uani 1 1 d . . . O5 O 0.3143(2) 0.2145(2) 0.1221(2) 0.0376(8) Uani 1 1 d D . . O6 O 0.0850(5) 0.1809(5) 0.2764(4) 0.141(3) Uani 1 1 d D . . O7 O 0.2276(5) 0.2259(7) 0.4102(8) 0.184(4) Uani 1 1 d D . . H1W H 0.320(3) 0.213(6) 0.0750(11) 0.20(4) Uiso 1 1 d D . . H2W H 0.3575(13) 0.215(3) 0.1610(17) 0.033(15) Uiso 1 1 d D . . H3W H 0.096(4) 0.191(4) 0.2328(19) 0.12(3) Uiso 1 1 d D . . H5W H 0.257(3) 0.189(2) 0.437(4) 0.18(3) Uiso 1 1 d D . . H4W H 0.121(3) 0.194(4) 0.3198(18) 0.09(3) Uiso 1 1 d D . . H6W H 0.251(3) 0.270(2) 0.407(5) 0.19(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(3) 0.035(3) 0.025(2) -0.001(2) 0.005(2) 0.003(2) C2 0.018(2) 0.033(3) 0.027(2) 0.001(2) 0.0007(19) 0.002(2) C3 0.023(3) 0.033(3) 0.029(2) -0.001(2) 0.008(2) 0.005(2) C4 0.019(2) 0.031(3) 0.030(2) 0.001(2) 0.0040(19) 0.006(2) C5 0.032(3) 0.037(3) 0.025(2) -0.002(2) 0.003(2) 0.012(2) C6 0.019(3) 0.036(3) 0.030(3) -0.004(2) 0.003(2) 0.005(2) C7 0.023(3) 0.033(3) 0.032(3) -0.001(2) 0.003(2) 0.009(2) C8 0.017(3) 0.035(3) 0.029(3) -0.001(2) 0.003(2) 0.005(2) C9 0.025(3) 0.034(3) 0.035(3) -0.003(2) 0.008(2) 0.005(2) C10 0.074(5) 0.135(7) 0.045(4) -0.041(4) -0.021(3) 0.073(5) C11 0.057(5) 0.101(6) 0.055(4) -0.024(4) -0.015(3) 0.057(4) C12 0.034(3) 0.077(4) 0.052(4) -0.031(3) -0.008(3) 0.022(3) C13 0.028(3) 0.069(4) 0.056(4) -0.026(3) -0.008(3) 0.026(3) C14 0.083(6) 0.046(4) 0.114(6) 0.006(4) 0.072(5) -0.003(4) C15 0.098(6) 0.046(4) 0.141(7) -0.007(4) 0.089(6) -0.005(4) C16 0.030(3) 0.039(3) 0.046(3) -0.001(3) 0.016(3) 0.001(2) C17 0.034(3) 0.044(3) 0.052(3) -0.005(3) 0.022(3) 0.004(3) C18 0.129(8) 0.070(5) 0.100(6) 0.027(4) 0.085(6) 0.054(5) C19 0.157(9) 0.081(5) 0.092(6) 0.035(4) 0.095(6) 0.056(5) C20 0.041(3) 0.044(3) 0.056(4) -0.009(3) 0.026(3) 0.003(3) C21 0.098(6) 0.038(3) 0.119(6) -0.015(4) 0.084(5) -0.005(4) C22 0.094(6) 0.035(3) 0.101(5) -0.003(3) 0.067(5) -0.004(3) N1 0.024(2) 0.036(2) 0.033(2) 0.0002(19) 0.0082(19) 0.0080(19) N2 0.024(2) 0.037(2) 0.038(2) 0.003(2) 0.0129(19) 0.0017(19) N3 0.038(3) 0.041(3) 0.053(3) -0.005(2) 0.022(2) 0.000(2) Ni1 0.0202(3) 0.0379(4) 0.0266(3) -0.0009(3) 0.0050(2) -0.0064(3) O1 0.029(2) 0.066(2) 0.0283(18) -0.0081(18) -0.0007(15) 0.0145(19) O2 0.051(3) 0.078(3) 0.041(2) -0.019(2) -0.003(2) 0.030(2) O3 0.030(2) 0.044(2) 0.0274(17) -0.0023(15) 0.0068(15) 0.0158(16) O4 0.029(2) 0.052(2) 0.0247(17) -0.0007(16) 0.0059(15) 0.0174(17) O5 0.032(2) 0.042(2) 0.035(2) -0.0034(18) 0.0062(18) -0.0004(18) O6 0.156(7) 0.217(8) 0.063(4) -0.003(5) 0.053(5) -0.076(6) O7 0.125(7) 0.155(8) 0.244(11) 0.009(8) 0.016(8) -0.013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.231(6) . ? C1 O1 1.263(6) . ? C1 C2 1.503(6) . ? C2 C3 1.374(6) . ? C2 C7 1.384(6) . ? C3 C4 1.386(6) . ? C3 H3 0.9300 . ? C4 C5 1.392(6) . ? C4 C8 1.507(6) . ? C5 C6 1.391(6) . ? C5 H5 0.9300 . ? C6 C7 1.393(6) . ? C6 C9 1.494(6) . ? C7 H7 0.9300 . ? C8 O3 1.266(5) . ? C8 O4 1.262(5) . ? C8 Ni1 2.477(5) 8_556 ? C9 C13 1.352(7) . ? C9 C10 1.358(8) . ? C10 C11 1.365(8) . ? C10 H10 0.9300 . ? C11 N1 1.291(7) . ? C11 H11 0.9300 . ? C12 N1 1.328(6) . ? C12 C13 1.363(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 N2 1.354(7) . ? C14 C15 1.356(8) . ? C14 H14 0.9300 . ? C15 N3 1.357(7) . ? C15 H15 0.9300 . ? C16 N2 1.305(5) . ? C16 N3 1.331(6) . ? C16 H16 0.9300 . ? C17 C18 1.341(8) . ? C17 C22 1.358(7) . ? C17 N3 1.437(6) . ? C18 C19 1.394(7) . ? C18 H18 0.9300 . ? C19 C20 1.356(8) . ? C19 H19 0.9300 . ? C20 C21 1.358(7) . ? C20 C20 1.490(9) 5_566 ? C21 C22 1.368(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N1 Ni1 2.068(4) 6_566 ? N2 Ni1 2.078(4) . ? Ni1 O1 2.013(3) . ? Ni1 N1 2.068(4) 6_565 ? Ni1 O5 2.077(4) . ? Ni1 O3 2.104(3) 8_455 ? Ni1 O4 2.195(3) 8_455 ? Ni1 C8 2.477(5) 8_455 ? O3 Ni1 2.104(3) 8_556 ? O4 Ni1 2.195(3) 8_556 ? O5 H1W 0.823(7) . ? O5 H2W 0.8200(11) . ? O6 H3W 0.820(4) . ? O6 H4W 0.822(4) . ? O7 H5W 0.8202(14) . ? O7 H6W 0.8200(18) . ? 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 C1 O1 125.4(5) . . ? O2 C1 C2 119.2(5) . . ? O1 C1 C2 115.3(4) . . ? C3 C2 C7 118.7(4) . . ? C3 C2 C1 121.1(4) . . ? C7 C2 C1 120.2(4) . . ? C2 C3 C4 121.2(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 119.2(4) . . ? C3 C4 C8 118.5(4) . . ? C5 C4 C8 122.2(4) . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 117.7(4) . . ? C5 C6 C9 121.8(4) . . ? C7 C6 C9 120.4(4) . . ? C2 C7 C6 122.1(4) . . ? C2 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? O3 C8 O4 120.4(4) . . ? O3 C8 C4 119.2(4) . . ? O4 C8 C4 120.4(4) . . ? O3 C8 Ni1 58.2(2) . 8_556 ? O4 C8 Ni1 62.3(2) . 8_556 ? C4 C8 Ni1 176.4(3) . 8_556 ? C13 C9 C10 113.6(5) . . ? C13 C9 C6 124.6(5) . . ? C10 C9 C6 121.7(5) . . ? C11 C10 C9 121.7(6) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.2 . . ? N1 C11 C10 125.2(6) . . ? N1 C11 H11 117.4 . . ? C10 C11 H11 117.4 . . ? N1 C12 C13 124.8(5) . . ? N1 C12 H12 117.6 . . ? C13 C12 H12 117.6 . . ? C9 C13 C12 121.3(5) . . ? C9 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? N2 C14 C15 110.2(5) . . ? N2 C14 H14 124.9 . . ? C15 C14 H14 124.9 . . ? N3 C15 C14 105.9(6) . . ? N3 C15 H15 127.0 . . ? C14 C15 H15 127.0 . . ? N2 C16 N3 112.9(4) . . ? N2 C16 H16 123.6 . . ? N3 C16 H16 123.6 . . ? C18 C17 C22 118.4(5) . . ? C18 C17 N3 121.3(5) . . ? C22 C17 N3 120.4(5) . . ? C17 C18 C19 120.6(6) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 121.9(6) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 115.8(5) . . ? C19 C20 C20 122.4(7) . 5_566 ? C21 C20 C20 121.7(6) . 5_566 ? C20 C21 C22 123.0(6) . . ? C20 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? C17 C22 C21 120.3(6) . . ? C17 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C11 N1 C12 113.4(4) . . ? C11 N1 Ni1 120.4(4) . 6_566 ? C12 N1 Ni1 126.1(4) . 6_566 ? C16 N2 C14 104.6(4) . . ? C16 N2 Ni1 123.1(3) . . ? C14 N2 Ni1 126.8(4) . . ? C16 N3 C15 106.4(4) . . ? C16 N3 C17 127.5(4) . . ? C15 N3 C17 126.0(5) . . ? O1 Ni1 N1 98.64(16) . 6_565 ? O1 Ni1 N2 83.85(15) . . ? N1 Ni1 N2 91.38(16) 6_565 . ? O1 Ni1 O5 90.47(14) . . ? N1 Ni1 O5 91.16(15) 6_565 . ? N2 Ni1 O5 174.07(15) . . ? O1 Ni1 O3 162.32(14) . 8_455 ? N1 Ni1 O3 98.92(14) 6_565 8_455 ? N2 Ni1 O3 97.81(15) . 8_455 ? O5 Ni1 O3 87.09(14) . 8_455 ? O1 Ni1 O4 101.13(14) . 8_455 ? N1 Ni1 O4 160.23(14) 6_565 8_455 ? N2 Ni1 O4 90.79(15) . 8_455 ? O5 Ni1 O4 88.63(14) . 8_455 ? O3 Ni1 O4 61.33(12) 8_455 8_455 ? O1 Ni1 C8 131.71(15) . 8_455 ? N1 Ni1 C8 129.64(15) 6_565 8_455 ? N2 Ni1 C8 94.63(16) . 8_455 ? O5 Ni1 C8 87.87(15) . 8_455 ? O3 Ni1 C8 30.73(12) 8_455 8_455 ? O4 Ni1 C8 30.60(12) 8_455 8_455 ? C1 O1 Ni1 131.0(3) . . ? C8 O3 Ni1 91.1(3) . 8_556 ? C8 O4 Ni1 87.1(3) . 8_556 ? Ni1 O5 H1W 118(6) . . ? Ni1 O5 H2W 104(3) . . ? H1W O5 H2W 114.5(4) . . ? H3W O6 H4W 114.7(3) . . ? H5W O7 H6W 114.6(2) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.586 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 949698' ####################################################################### # # 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_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H25 Cu N5 O4, 4(H2 O)' _chemical_formula_sum 'C33 H33 Cu N5 O8' _chemical_formula_weight 691.18 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' Cu Cu 0.3201 1.2651 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.8210(12) _cell_length_b 19.1858(14) _cell_length_c 20.6555(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6666.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1196 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 16.12 _exptl_crystal_description block _exptl_crystal_colour blie _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2872 _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8706 _exptl_absorpt_correction_T_max 0.9321 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _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 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 32497 _diffrn_reflns_av_R_equivalents 0.1541 _diffrn_reflns_av_sigmaI/netI 0.1058 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5870 _reflns_number_gt 2945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^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 5870 _refine_ls_number_parameters 448 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1506 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1747 _refine_ls_wR_factor_gt 0.1512 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 C1 C 0.3388(3) 0.9829(3) 0.1897(3) 0.0472(16) Uani 1 1 d . . . H1 H 0.3475 0.9497 0.1576 0.057 Uiso 1 1 calc R . . C2 C 0.3501(4) 1.0439(3) 0.2758(3) 0.0526(17) Uani 1 1 d . . . H2 H 0.3690 1.0607 0.3151 0.063 Uiso 1 1 calc R . . C3 C 0.2863(4) 1.0691(3) 0.2437(3) 0.0585(18) Uani 1 1 d . . . H3 H 0.2538 1.1058 0.2566 0.070 Uiso 1 1 calc R . . C4 C 0.2168(4) 1.0395(4) 0.1396(3) 0.073(2) Uani 1 1 d . . . H4A H 0.2183 1.0874 0.1245 0.087 Uiso 1 1 calc R . . H4B H 0.1655 1.0319 0.1598 0.087 Uiso 1 1 calc R . . C5 C 0.2241(4) 0.9924(4) 0.0831(3) 0.0544(17) Uani 1 1 d . . . C6 C 0.2822(4) 1.0035(4) 0.0359(3) 0.072(2) Uani 1 1 d . . . H6 H 0.3169 1.0410 0.0394 0.087 Uiso 1 1 calc R . . C7 C 0.2875(4) 0.9587(4) -0.0157(3) 0.068(2) Uani 1 1 d . . . H7 H 0.3268 0.9665 -0.0466 0.082 Uiso 1 1 calc R . . C8 C 0.2359(4) 0.9013(4) -0.0237(3) 0.0526(17) Uani 1 1 d . . . C9 C 0.1795(4) 0.8916(4) 0.0236(3) 0.066(2) Uani 1 1 d . . . H9 H 0.1449 0.8540 0.0206 0.079 Uiso 1 1 calc R . . C10 C 0.1730(4) 0.9368(4) 0.0760(3) 0.069(2) Uani 1 1 d . . . H10 H 0.1334 0.9294 0.1068 0.082 Uiso 1 1 calc R . . C11 C 0.2435(4) 0.8534(3) -0.0786(3) 0.0478(16) Uani 1 1 d . . . C12 C 0.3143(4) 0.8396(4) -0.1092(3) 0.0584(18) Uani 1 1 d . . . H12 H 0.3599 0.8626 -0.0953 0.070 Uiso 1 1 calc R . . C13 C 0.3203(4) 0.7927(3) -0.1598(3) 0.0552(17) Uani 1 1 d . . . H13 H 0.3695 0.7850 -0.1789 0.066 Uiso 1 1 calc R . . C14 C 0.2554(4) 0.7577(3) -0.1822(3) 0.0540(17) Uani 1 1 d . . . C15 C 0.1830(4) 0.7719(4) -0.1538(4) 0.077(2) Uani 1 1 d . . . H15 H 0.1375 0.7497 -0.1689 0.093 Uiso 1 1 calc R . . C16 C 0.1773(4) 0.8190(4) -0.1027(4) 0.071(2) Uani 1 1 d . . . H16 H 0.1278 0.8276 -0.0843 0.086 Uiso 1 1 calc R . . C17 C 0.2622(4) 0.7090(4) -0.2383(3) 0.066(2) Uani 1 1 d . . . H17A H 0.2507 0.7341 -0.2780 0.080 Uiso 1 1 calc R . . H17B H 0.3164 0.6919 -0.2410 0.080 Uiso 1 1 calc R . . C18 C 0.2180(4) 0.5930(4) -0.1957(4) 0.076(2) Uani 1 1 d . . . H18 H 0.2627 0.5820 -0.1712 0.091 Uiso 1 1 calc R . . C19 C 0.1346(4) 0.6449(3) -0.2577(3) 0.0531(16) Uani 1 1 d . . . H19 H 0.1121 0.6782 -0.2847 0.064 Uiso 1 1 calc R . . N4 N 0.0981(3) 0.5875(3) -0.2398(2) 0.0476(12) Uani 1 1 d . . . C21 C 0.5271(3) 1.0878(3) 0.2781(3) 0.0393(14) Uani 1 1 d . . . C22 C 0.5371(3) 1.1436(3) 0.3297(2) 0.0301(12) Uani 1 1 d . . . C23 C 0.5379(3) 1.2136(3) 0.3135(2) 0.0339(13) Uani 1 1 d . . . H23 H 0.5344 1.2266 0.2702 0.041 Uiso 1 1 calc R . . C24 C 0.5439(3) 1.2648(3) 0.3607(2) 0.0353(13) Uani 1 1 d . . . C25 C 0.5490(3) 1.2450(3) 0.4257(2) 0.0372(13) Uani 1 1 d . . . H25 H 0.5531 1.2789 0.4577 0.045 Uiso 1 1 calc R . . C26 C 0.5479(3) 1.1741(3) 0.4428(2) 0.0336(13) Uani 1 1 d . . . C27 C 0.5401(3) 1.1246(3) 0.3942(2) 0.0339(13) Uani 1 1 d . . . H27 H 0.5369 1.0777 0.4053 0.041 Uiso 1 1 calc R . . C28 C 0.5412(3) 1.3410(3) 0.3420(3) 0.0382(14) Uani 1 1 d . . . C29 C 0.5490(3) 1.1522(3) 0.5127(2) 0.0339(13) Uani 1 1 d . . . C30 C 0.5247(3) 1.1944(3) 0.5624(2) 0.0423(15) Uani 1 1 d . . . H30 H 0.5099 1.2402 0.5540 0.051 Uiso 1 1 calc R . . C31 C 0.5223(4) 1.1688(3) 0.6253(3) 0.0451(15) Uani 1 1 d . . . H31 H 0.5061 1.1989 0.6580 0.054 Uiso 1 1 calc R . . C32 C 0.5670(4) 1.0642(3) 0.5935(3) 0.0539(17) Uani 1 1 d . . . H32 H 0.5822 1.0189 0.6035 0.065 Uiso 1 1 calc R . . C33 C 0.5721(4) 1.0853(3) 0.5300(3) 0.0504(17) Uani 1 1 d . . . H33 H 0.5911 1.0547 0.4987 0.060 Uiso 1 1 calc R . . Cu1 Cu 0.48611(4) 0.94189(3) 0.25633(3) 0.0361(2) Uani 1 1 d . . . N1 N 0.3828(3) 0.9897(2) 0.2415(2) 0.0429(12) Uani 1 1 d . . . N2 N 0.2792(3) 1.0300(3) 0.1885(2) 0.0473(13) Uani 1 1 d . . . N3 N 0.2081(3) 0.6501(3) -0.2325(3) 0.0566(14) Uani 1 1 d . . . C20 C 0.1518(4) 0.5551(4) -0.2009(3) 0.0663(19) Uani 1 1 d . . . H20 H 0.1436 0.5124 -0.1806 0.080 Uiso 1 1 calc R . . N5 N 0.5415(3) 1.1048(2) 0.6415(2) 0.0431(13) Uani 1 1 d . . . O1 O 0.5505(2) 1.35384(18) 0.28241(17) 0.0398(9) Uani 1 1 d . . . O2 O 0.5292(3) 1.38549(19) 0.38503(18) 0.0572(12) Uani 1 1 d . . . O3 O 0.5227(3) 1.1049(2) 0.22117(18) 0.0597(12) Uani 1 1 d . . . O4 O 0.5250(2) 1.02597(18) 0.30006(17) 0.0434(10) Uani 1 1 d . . . O5 O 0.5121(4) 0.0295(3) 0.1051(2) 0.0909(18) Uani 1 1 d D . . O6 O 0.4582(4) 0.3787(5) 0.5112(3) 0.129(2) Uani 1 1 d D . . O7 O 0.3955(5) 0.2042(4) 0.1762(3) 0.136(2) Uani 1 1 d D . . O8 O 0.3153(8) 0.1944(5) 0.0402(6) 0.321(8) Uani 1 1 d D . . H7W H 0.351(2) 0.223(2) 0.334(3) 0.080 Uiso 1 1 d D . . H8W H 0.327(3) 0.163(2) 0.365(3) 0.080 Uiso 1 1 d D . . H1W H 0.506(3) 0.048(3) 0.1408(11) 0.080 Uiso 1 1 d D . . H3W H 0.5066(8) 0.373(4) 0.512(3) 0.080 Uiso 1 1 d D . . H4W H 0.441(3) 0.396(4) 0.4776(19) 0.080 Uiso 1 1 d D . . H5W H 0.426(2) 0.182(3) 0.152(2) 0.080 Uiso 1 1 d D . . H6W H 0.355(3) 0.218(4) 0.159(2) 0.080 Uiso 1 1 d D . . H2W H 0.490(4) 0.050(3) 0.0754(15) 0.080 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.048(4) 0.043(4) 0.051(4) -0.010(3) 0.001(3) 0.010(3) C2 0.068(5) 0.042(4) 0.048(4) -0.012(3) 0.006(3) 0.000(3) C3 0.066(5) 0.047(4) 0.062(4) -0.014(4) -0.002(4) 0.013(3) C4 0.063(5) 0.090(6) 0.064(5) 0.004(4) -0.011(4) 0.025(4) C5 0.056(5) 0.062(5) 0.045(4) -0.001(4) -0.003(3) 0.017(4) C6 0.077(5) 0.076(6) 0.063(5) -0.012(4) 0.003(4) -0.020(4) C7 0.066(5) 0.084(6) 0.055(4) -0.006(4) 0.013(4) -0.013(4) C8 0.045(4) 0.065(5) 0.048(4) 0.003(4) -0.001(3) -0.007(4) C9 0.062(5) 0.062(5) 0.073(5) -0.006(4) 0.003(4) -0.014(4) C10 0.069(5) 0.078(6) 0.059(5) 0.017(4) 0.013(4) 0.003(5) C11 0.047(4) 0.046(4) 0.051(4) 0.005(3) -0.001(3) -0.002(3) C12 0.043(4) 0.068(5) 0.064(4) 0.003(4) -0.006(3) -0.016(4) C13 0.040(4) 0.060(4) 0.066(4) -0.003(4) 0.001(3) -0.007(3) C14 0.042(4) 0.054(4) 0.066(4) -0.007(4) 0.003(3) -0.007(3) C15 0.051(5) 0.083(6) 0.098(6) -0.033(5) 0.002(4) -0.014(4) C16 0.048(5) 0.071(5) 0.095(6) -0.014(5) 0.005(4) 0.001(4) C17 0.054(4) 0.066(5) 0.079(5) -0.019(4) 0.005(4) -0.013(4) C18 0.052(5) 0.074(5) 0.102(6) -0.008(5) -0.021(4) 0.003(4) C19 0.049(4) 0.054(4) 0.056(4) -0.002(4) -0.004(3) -0.009(3) N4 0.052(3) 0.037(3) 0.054(3) -0.008(3) -0.004(3) 0.003(3) C21 0.052(4) 0.032(3) 0.034(3) -0.003(3) 0.000(3) -0.004(3) C22 0.040(3) 0.022(3) 0.028(3) 0.000(2) 0.006(2) -0.001(2) C23 0.044(4) 0.031(3) 0.026(3) 0.006(3) -0.002(2) -0.001(3) C24 0.052(4) 0.029(3) 0.025(3) 0.000(2) -0.002(2) 0.001(3) C25 0.047(3) 0.031(3) 0.034(3) -0.003(3) 0.000(3) -0.003(3) C26 0.042(3) 0.028(3) 0.032(3) 0.002(3) 0.002(2) 0.002(3) C27 0.046(4) 0.023(3) 0.032(3) 0.003(3) 0.004(3) 0.001(3) C28 0.045(4) 0.026(3) 0.044(4) 0.004(3) -0.002(3) 0.001(3) C29 0.041(3) 0.031(3) 0.030(3) -0.002(3) -0.003(2) -0.004(3) C30 0.062(4) 0.029(3) 0.036(3) -0.001(3) -0.001(3) -0.003(3) C31 0.071(4) 0.036(4) 0.028(3) -0.002(3) 0.001(3) -0.002(3) C32 0.090(5) 0.033(4) 0.039(3) 0.006(3) 0.004(3) 0.017(4) C33 0.081(5) 0.037(4) 0.033(3) 0.006(3) 0.011(3) 0.013(3) Cu1 0.0501(4) 0.0260(3) 0.0322(4) -0.0045(3) -0.0011(3) 0.0002(3) N1 0.051(3) 0.035(3) 0.043(3) -0.008(2) -0.008(3) 0.004(2) N2 0.052(3) 0.048(3) 0.042(3) 0.000(3) -0.002(2) 0.010(3) N3 0.051(4) 0.050(4) 0.068(4) -0.005(3) -0.002(3) -0.005(3) C20 0.068(5) 0.049(4) 0.082(5) 0.003(4) -0.016(4) 0.002(4) N5 0.070(4) 0.032(3) 0.027(2) 0.002(2) -0.001(2) -0.003(3) O1 0.059(3) 0.030(2) 0.030(2) 0.0116(18) 0.0033(18) 0.0038(19) O2 0.105(4) 0.026(2) 0.040(2) -0.001(2) 0.007(2) -0.001(2) O3 0.107(4) 0.044(3) 0.028(2) -0.003(2) 0.002(2) -0.013(2) O4 0.064(3) 0.025(2) 0.041(2) -0.0040(18) -0.011(2) 0.002(2) O5 0.153(5) 0.079(4) 0.040(3) -0.001(3) 0.001(3) -0.008(3) O6 0.173(7) 0.123(6) 0.093(5) -0.010(5) 0.033(4) 0.014(6) O7 0.170(8) 0.090(6) 0.148(6) 0.014(5) 0.010(5) 0.009(5) O8 0.58(2) 0.117(9) 0.264(13) 0.001(8) 0.199(15) -0.066(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.308(6) . ? C1 N2 1.351(7) . ? C1 H1 0.9300 . ? C2 C3 1.349(8) . ? C2 N1 1.374(7) . ? C2 H2 0.9300 . ? C3 N2 1.371(7) . ? C3 H3 0.9300 . ? C4 N2 1.468(7) . ? C4 C5 1.481(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.378(9) . ? C5 C6 1.396(9) . ? C6 C7 1.372(9) . ? C6 H6 0.9300 . ? C7 C8 1.412(9) . ? C7 H7 0.9300 . ? C8 C9 1.375(8) . ? C8 C11 1.465(8) . ? C9 C10 1.391(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.375(8) . ? C11 C16 1.387(8) . ? C12 C13 1.383(8) . ? C12 H12 0.9300 . ? C13 C14 1.363(8) . ? C13 H13 0.9300 . ? C14 C15 1.378(8) . ? C14 C17 1.493(8) . ? C15 C16 1.393(9) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 N3 1.456(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N3 1.344(8) . ? C18 C20 1.334(9) . ? C18 H18 0.9300 . ? C19 N4 1.314(7) . ? C19 N3 1.344(7) . ? C19 H19 0.9300 . ? N4 C20 1.359(7) . ? N4 Cu1 1.996(5) 3_465 ? C21 O3 1.224(6) . ? C21 O4 1.271(6) . ? C21 C22 1.518(7) . ? C22 C27 1.382(6) . ? C22 C23 1.386(7) . ? C23 C24 1.387(7) . ? C23 H23 0.9300 . ? C24 C25 1.397(7) . ? C24 C28 1.513(7) . ? C25 C26 1.405(7) . ? C25 H25 0.9300 . ? C26 C27 1.388(7) . ? C26 C29 1.504(7) . ? C27 H27 0.9300 . ? C28 O2 1.248(6) . ? C28 O1 1.266(6) . ? C29 C30 1.370(7) . ? C29 C33 1.389(7) . ? C30 C31 1.390(7) . ? C30 H30 0.9300 . ? C31 N5 1.311(7) . ? C31 H31 0.9300 . ? C32 N5 1.332(6) . ? C32 C33 1.374(7) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? Cu1 O4 1.961(3) . ? Cu1 O1 1.968(3) 4_645 ? Cu1 N1 1.989(5) . ? Cu1 N4 1.996(5) 3_565 ? Cu1 N5 2.340(4) 5_676 ? C20 H20 0.9300 . ? N5 Cu1 2.340(4) 5_676 ? O1 Cu1 1.968(3) 4_655 ? O5 H1W 0.8199(11) . ? O5 H2W 0.8200(11) . ? O6 H3W 0.8200(12) . ? O6 H4W 0.8200(10) . ? O7 H5W 0.8201(11) . ? O7 H6W 0.8201(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 111.5(5) . . ? N1 C1 H1 124.2 . . ? N2 C1 H1 124.2 . . ? C3 C2 N1 109.7(5) . . ? C3 C2 H2 125.2 . . ? N1 C2 H2 125.2 . . ? C2 C3 N2 106.3(5) . . ? C2 C3 H3 126.8 . . ? N2 C3 H3 126.8 . . ? N2 C4 C5 114.0(5) . . ? N2 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? N2 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C10 C5 C6 118.7(6) . . ? C10 C5 C4 120.3(7) . . ? C6 C5 C4 121.0(7) . . ? C7 C6 C5 119.5(7) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 122.6(6) . . ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C9 C8 C7 116.5(6) . . ? C9 C8 C11 121.7(6) . . ? C7 C8 C11 121.8(6) . . ? C8 C9 C10 121.6(7) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C5 C10 C9 121.0(6) . . ? C5 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C16 116.0(6) . . ? C12 C11 C8 123.5(6) . . ? C16 C11 C8 120.4(6) . . ? C11 C12 C13 122.4(6) . . ? C11 C12 H12 118.8 . . ? C13 C12 H12 118.8 . . ? C14 C13 C12 121.3(6) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 117.8(6) . . ? C13 C14 C17 120.7(6) . . ? C15 C14 C17 121.5(6) . . ? C14 C15 C16 120.8(6) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C11 C16 C15 121.7(6) . . ? C11 C16 H16 119.2 . . ? C15 C16 H16 119.1 . . ? N3 C17 C14 112.0(5) . . ? N3 C17 H17A 109.2 . . ? C14 C17 H17A 109.2 . . ? N3 C17 H17B 109.2 . . ? C14 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? N3 C18 C20 107.2(7) . . ? N3 C18 H18 126.4 . . ? C20 C18 H18 126.4 . . ? N4 C19 N3 112.5(6) . . ? N4 C19 H19 123.7 . . ? N3 C19 H19 123.7 . . ? C19 N4 C20 103.8(5) . . ? C19 N4 Cu1 129.0(4) . 3_465 ? C20 N4 Cu1 126.8(5) . 3_465 ? O3 C21 O4 126.2(5) . . ? O3 C21 C22 119.6(5) . . ? O4 C21 C22 114.3(5) . . ? C27 C22 C23 119.2(5) . . ? C27 C22 C21 119.7(5) . . ? C23 C22 C21 121.0(5) . . ? C22 C23 C24 121.1(5) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C23 C24 C25 119.2(5) . . ? C23 C24 C28 120.1(4) . . ? C25 C24 C28 120.6(5) . . ? C24 C25 C26 120.2(5) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C27 C26 C25 118.8(5) . . ? C27 C26 C29 120.2(5) . . ? C25 C26 C29 120.8(5) . . ? C22 C27 C26 121.4(5) . . ? C22 C27 H27 119.3 . . ? C26 C27 H27 119.3 . . ? O2 C28 O1 125.3(5) . . ? O2 C28 C24 119.0(5) . . ? O1 C28 C24 115.6(5) . . ? C30 C29 C33 115.8(5) . . ? C30 C29 C26 123.4(5) . . ? C33 C29 C26 120.7(5) . . ? C29 C30 C31 120.1(5) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? N5 C31 C30 124.2(5) . . ? N5 C31 H31 117.9 . . ? C30 C31 H31 117.9 . . ? N5 C32 C33 124.0(5) . . ? N5 C32 H32 118.0 . . ? C33 C32 H32 118.0 . . ? C32 C33 C29 120.0(5) . . ? C32 C33 H33 120.0 . . ? C29 C33 H33 120.0 . . ? O4 Cu1 O1 176.11(15) . 4_645 ? O4 Cu1 N1 89.03(17) . . ? O1 Cu1 N1 93.42(17) 4_645 . ? O4 Cu1 N4 89.79(18) . 3_565 ? O1 Cu1 N4 89.05(17) 4_645 3_565 ? N1 Cu1 N4 158.2(2) . 3_565 ? O4 Cu1 N5 88.05(15) . 5_676 ? O1 Cu1 N5 88.61(15) 4_645 5_676 ? N1 Cu1 N5 98.19(18) . 5_676 ? N4 Cu1 N5 103.51(19) 3_565 5_676 ? C1 N1 C2 105.8(5) . . ? C1 N1 Cu1 125.1(4) . . ? C2 N1 Cu1 128.3(4) . . ? C1 N2 C3 106.7(5) . . ? C1 N2 C4 128.7(5) . . ? C3 N2 C4 124.6(5) . . ? C18 N3 C19 105.8(6) . . ? C18 N3 C17 126.9(6) . . ? C19 N3 C17 126.9(6) . . ? N4 C20 C18 110.7(7) . . ? N4 C20 H20 124.7 . . ? C18 C20 H20 124.7 . . ? C31 N5 C32 115.9(5) . . ? C31 N5 Cu1 122.6(4) . 5_676 ? C32 N5 Cu1 120.8(4) . 5_676 ? C28 O1 Cu1 121.6(4) . 4_655 ? C21 O4 Cu1 127.8(3) . . ? H1W O5 H2W 114.6(2) . . ? H3W O6 H4W 114.6(2) . . ? H5W O7 H6W 114.5(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.761 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 949699'