# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 Cd N4 O4' _chemical_formula_weight 430.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 22.0941(10) _cell_length_b 22.0941(10) _cell_length_c 14.5099(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7083.0(8) _cell_formula_units_Z 16 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1983 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.20 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3456 _exptl_absorpt_coefficient_mu 1.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6329 _exptl_absorpt_correction_T_max 0.7869 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; Because the installation location of the crystal is inappropriate, leading to the low completeness of 0.832 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15669 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3662 _reflns_number_gt 2662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+125.1259P] 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 3662 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.2071 _refine_ls_wR_factor_gt 0.1996 _refine_ls_goodness_of_fit_ref 1.239 _refine_ls_restrained_S_all 1.239 _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 0.6416(4) 0.6976(4) 0.2619(7) 0.039(2) Uani 1 1 d . . . C2 C 0.6998(4) 0.6689(4) 0.2432(6) 0.0342(18) Uani 1 1 d . . . C3 C 0.7547(4) 0.6686(4) 0.2886(6) 0.0331(18) Uani 1 1 d . . . C4 C 0.7736(5) 0.6981(5) 0.3772(7) 0.046(2) Uani 1 1 d . . . C5 C 0.7638(4) 0.6179(5) 0.1618(7) 0.045(2) Uani 1 1 d . . . C6 C 0.5835(5) 0.7223(5) -0.0905(7) 0.045(2) Uani 1 1 d . . . H6A H 0.5598 0.7561 -0.1135 0.054 Uiso 1 1 calc R . . H6B H 0.5757 0.6875 -0.1295 0.054 Uiso 1 1 calc R . . C7 C 0.6495(6) 0.7379(6) -0.0934(8) 0.062(3) Uani 1 1 d . . . H7A H 0.6560 0.7763 -0.0627 0.074 Uiso 1 1 calc R . . H7B H 0.6622 0.7422 -0.1571 0.074 Uiso 1 1 calc R . . N1 N 0.7060(4) 0.6363(4) 0.1624(6) 0.046(2) Uani 1 1 d . A . N2 N 0.7957(3) 0.6363(3) 0.2393(5) 0.0323(15) Uani 1 1 d . A . N3 N 0.5660(4) 0.7089(4) 0.0035(6) 0.0414(18) Uani 1 1 d . A . H3A H 0.5275 0.6957 0.0048 0.050 Uiso 1 1 calc R . . H3B H 0.5684 0.7426 0.0380 0.050 Uiso 1 1 calc R . . N4 N 0.6875(4) 0.6900(5) -0.0474(7) 0.062(3) Uani 1 1 d . A . H4A H 0.7194 0.7073 -0.0193 0.075 Uiso 1 1 calc R . . H4B H 0.7016 0.6640 -0.0901 0.075 Uiso 1 1 calc R . . O1 O 0.5997(3) 0.6950(3) 0.2070(5) 0.0485(18) Uani 1 1 d . A . O2 O 0.6365(3) 0.7261(4) 0.3416(5) 0.0519(19) Uani 1 1 d . . . H2 H 0.6686 0.7236 0.3699 0.078 Uiso 1 1 calc R . . O3 O 0.7348(4) 0.7282(4) 0.4198(6) 0.059(2) Uani 1 1 d . . . O4 O 0.8253(4) 0.6904(4) 0.4021(6) 0.055(2) Uani 1 1 d . . . Cd1 Cd 0.62832(3) 0.63653(3) 0.06278(5) 0.0379(2) Uani 1 1 d . . . C1A C 0.8044(10) 0.5964(11) 0.0818(15) 0.038(4) Uani 0.488(10) 1 d P A 1 C2A C 0.8149(9) 0.5351(9) 0.0674(14) 0.038(4) Uani 0.488(10) 1 d P A 1 H2A H 0.7972 0.5065 0.1061 0.046 Uiso 0.488(10) 1 calc PR A 1 C3A C 0.852(3) 0.516(2) -0.005(6) 0.038(10) Uani 0.488(10) 1 d P A 1 H3A1 H 0.8588 0.4754 -0.0144 0.046 Uiso 0.488(10) 1 calc PR A 1 C4A C 0.8783(9) 0.5591(10) -0.0625(16) 0.038(4) Uani 0.488(10) 1 d P A 1 C5A C 0.8678(9) 0.6204(9) -0.0481(13) 0.038(4) Uani 0.488(10) 1 d P A 1 C6A C 0.8308(9) 0.6390(9) 0.0240(13) 0.038(4) Uani 0.488(10) 1 d P A 1 H6A1 H 0.8238 0.6800 0.0337 0.046 Uiso 0.488(10) 1 calc PR A 1 C7A C 0.9262(9) 0.5445(9) -0.1349(14) 0.038(4) Uani 0.488(10) 1 d P A 1 H7A1 H 0.9304 0.5015 -0.1405 0.058 Uiso 0.488(10) 1 calc PR A 1 H7A2 H 0.9642 0.5618 -0.1165 0.058 Uiso 0.488(10) 1 calc PR A 1 H7A3 H 0.9142 0.5613 -0.1931 0.058 Uiso 0.488(10) 1 calc PR A 1 C8A C 0.8956(9) 0.6680(9) -0.1097(14) 0.038(4) Uani 0.488(10) 1 d P A 1 H8A1 H 0.9194 0.6487 -0.1567 0.058 Uiso 0.488(10) 1 calc PR A 1 H8A2 H 0.9211 0.6940 -0.0736 0.058 Uiso 0.488(10) 1 calc PR A 1 H8A3 H 0.8641 0.6914 -0.1380 0.058 Uiso 0.488(10) 1 calc PR A 1 C1B C 0.7854(10) 0.5674(10) 0.0970(14) 0.038(4) Uani 0.512(10) 1 d P A 2 C2B C 0.7528(9) 0.5146(8) 0.0815(13) 0.038(4) Uani 0.512(10) 1 d P A 2 H2B H 0.7161 0.5084 0.1116 0.046 Uiso 0.512(10) 1 calc PR A 2 C3B C 0.7749(8) 0.4710(8) 0.0212(13) 0.038(4) Uani 0.512(10) 1 d P A 2 H3B1 H 0.7531 0.4357 0.0109 0.046 Uiso 0.512(10) 1 calc PR A 2 C4B C 0.8297(9) 0.4803(10) -0.0237(14) 0.038(4) Uani 0.512(10) 1 d P A 2 C5B C 0.862(3) 0.533(2) -0.008(6) 0.038(9) Uani 0.512(10) 1 d P A 2 C6B C 0.8402(9) 0.5767(9) 0.0521(13) 0.038(4) Uani 0.512(10) 1 d P A 2 H6B1 H 0.8621 0.6120 0.0624 0.046 Uiso 0.512(10) 1 calc PR A 2 C7B C 0.8551(8) 0.4292(8) -0.0804(13) 0.038(4) Uani 0.512(10) 1 d P A 2 H7B1 H 0.8262 0.3968 -0.0831 0.058 Uiso 0.512(10) 1 calc PR A 2 H7B2 H 0.8918 0.4149 -0.0526 0.058 Uiso 0.512(10) 1 calc PR A 2 H7B3 H 0.8635 0.4434 -0.1416 0.058 Uiso 0.512(10) 1 calc PR A 2 C8B C 0.9218(9) 0.5397(8) -0.0557(13) 0.038(4) Uani 0.512(10) 1 d P A 2 H8B1 H 0.9289 0.5049 -0.0939 0.058 Uiso 0.512(10) 1 calc PR A 2 H8B2 H 0.9534 0.5429 -0.0106 0.058 Uiso 0.512(10) 1 calc PR A 2 H8B3 H 0.9214 0.5754 -0.0932 0.058 Uiso 0.512(10) 1 calc PR A 2 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 0.038(5) 0.037(5) 0.040(5) -0.016(4) 0.007(4) -0.001(4) C2 0.037(4) 0.035(4) 0.031(4) -0.009(4) 0.001(4) 0.001(4) C3 0.038(5) 0.032(4) 0.029(4) 0.001(3) -0.001(3) -0.003(3) C4 0.056(6) 0.044(5) 0.038(5) -0.012(4) -0.012(5) -0.001(5) C5 0.035(5) 0.066(7) 0.034(5) -0.023(5) -0.008(4) 0.015(5) C6 0.055(6) 0.039(5) 0.041(5) 0.003(4) 0.007(5) -0.007(4) C7 0.075(8) 0.064(7) 0.047(6) -0.011(6) 0.003(6) -0.033(6) N1 0.038(4) 0.060(5) 0.040(4) -0.028(4) -0.013(4) 0.015(4) N2 0.033(4) 0.040(4) 0.024(3) -0.001(3) -0.004(3) 0.001(3) N3 0.048(4) 0.031(4) 0.045(4) 0.000(3) 0.004(4) 0.000(3) N4 0.041(5) 0.100(8) 0.045(5) -0.014(5) 0.006(4) -0.020(5) O1 0.041(4) 0.045(4) 0.060(4) -0.019(3) -0.006(3) 0.007(3) O2 0.045(4) 0.063(5) 0.048(4) -0.025(4) 0.002(3) 0.014(3) O3 0.065(5) 0.062(5) 0.051(5) -0.023(4) -0.008(4) 0.022(4) O4 0.059(5) 0.053(4) 0.054(4) -0.019(4) -0.022(4) 0.008(4) Cd1 0.0337(4) 0.0399(4) 0.0401(4) -0.0118(3) -0.0069(3) 0.0050(3) C1A 0.039(11) 0.036(11) 0.040(11) -0.014(9) 0.006(9) -0.001(9) C2A 0.039(10) 0.036(10) 0.040(10) -0.014(8) 0.006(8) -0.001(8) C3A 0.04(2) 0.04(3) 0.040(14) -0.01(2) 0.006(16) -0.001(18) C4A 0.039(11) 0.036(10) 0.040(11) -0.014(9) 0.006(9) -0.001(8) C5A 0.039(10) 0.036(9) 0.040(10) -0.014(8) 0.006(8) -0.001(8) C6A 0.039(10) 0.036(10) 0.040(10) -0.014(8) 0.006(8) -0.001(8) C7A 0.039(10) 0.036(9) 0.040(11) -0.014(8) 0.006(8) -0.001(8) C8A 0.039(10) 0.036(9) 0.040(10) -0.014(8) 0.006(8) -0.001(8) C1B 0.039(10) 0.036(10) 0.040(10) -0.014(9) 0.006(8) -0.001(9) C2B 0.039(9) 0.036(9) 0.040(10) -0.014(8) 0.006(8) -0.001(7) C3B 0.039(9) 0.036(9) 0.040(10) -0.014(8) 0.006(8) -0.001(7) C4B 0.039(10) 0.036(10) 0.040(10) -0.014(8) 0.006(8) -0.001(8) C5B 0.04(2) 0.04(2) 0.040(16) -0.01(2) 0.006(16) -0.001(16) C6B 0.039(10) 0.036(10) 0.040(10) -0.014(8) 0.006(8) -0.001(8) C7B 0.039(9) 0.036(9) 0.040(10) -0.014(8) 0.006(8) -0.001(7) C8B 0.039(10) 0.036(9) 0.040(10) -0.014(8) 0.006(8) -0.001(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 O1 1.222(12) . ? C1 O2 1.322(11) . ? C1 C2 1.459(12) . ? C2 C3 1.381(12) . ? C2 N1 1.383(11) . ? C3 N2 1.357(11) . ? C3 C4 1.500(12) . ? C4 O4 1.212(13) . ? C4 O3 1.249(13) . ? C5 N1 1.341(12) . ? C5 N2 1.388(11) . ? C5 C1B 1.53(2) . ? C5 C1A 1.54(2) . ? C6 N3 1.449(13) . ? C6 C7 1.500(16) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N4 1.506(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N1 Cd1 2.244(8) . ? N2 Cd1 2.296(7) 8_454 ? N3 Cd1 2.278(8) . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? N4 Cd1 2.379(10) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? O1 Cd1 2.539(7) . ? O2 H2 0.8200 . ? O4 Cd1 2.412(8) 8_454 ? Cd1 N2 2.296(7) 7_544 ? Cd1 O4 2.412(8) 7_544 ? C1A C2A 1.39(3) . ? C1A C6A 1.39(3) . ? C2A C3A 1.39(8) . ? C2A H2A 0.9300 . ? C3A C4A 1.39(6) . ? C3A H3A1 0.9300 . ? C4A C5A 1.39(3) . ? C4A C7A 1.53(3) . ? C5A C6A 1.39(2) . ? C5A C8A 1.51(3) . ? C6A H6A1 0.9300 . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? C1B C2B 1.39(3) . ? C1B C6B 1.39(3) . ? C2B C3B 1.39(2) . ? C2B H2B 0.9300 . ? C3B C4B 1.39(3) . ? C3B H3B1 0.9300 . ? C4B C5B 1.39(4) . ? C4B C7B 1.50(3) . ? C5B C6B 1.39(7) . ? C5B C8B 1.49(6) . ? C6B H6B1 0.9300 . ? C7B H7B1 0.9600 . ? C7B H7B2 0.9600 . ? C7B H7B3 0.9600 . ? C8B H8B1 0.9600 . ? C8B H8B2 0.9600 . ? C8B H8B3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 122.0(9) . . ? O1 C1 C2 121.7(8) . . ? O2 C1 C2 116.4(8) . . ? C3 C2 N1 108.4(8) . . ? C3 C2 C1 133.5(8) . . ? N1 C2 C1 118.1(8) . . ? N2 C3 C2 109.7(7) . . ? N2 C3 C4 119.7(8) . . ? C2 C3 C4 130.6(9) . . ? O4 C4 O3 125.0(9) . . ? O4 C4 C3 117.2(10) . . ? O3 C4 C3 117.7(9) . . ? N1 C5 N2 112.9(8) . . ? N1 C5 C1B 121.4(11) . . ? N2 C5 C1B 123.5(11) . . ? N1 C5 C1A 130.7(11) . . ? N2 C5 C1A 113.9(11) . . ? C1B C5 C1A 30.0(9) . . ? N3 C6 C7 109.4(9) . . ? N3 C6 H6A 109.8 . . ? C7 C6 H6A 109.8 . . ? N3 C6 H6B 109.8 . . ? C7 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C6 C7 N4 111.6(9) . . ? C6 C7 H7A 109.3 . . ? N4 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? N4 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C5 N1 C2 104.9(7) . . ? C5 N1 Cd1 136.5(6) . . ? C2 N1 Cd1 118.0(6) . . ? C3 N2 C5 104.1(7) . . ? C3 N2 Cd1 114.3(5) . 8_454 ? C5 N2 Cd1 141.1(6) . 8_454 ? C6 N3 Cd1 109.8(6) . . ? C6 N3 H3A 109.7 . . ? Cd1 N3 H3A 109.7 . . ? C6 N3 H3B 109.7 . . ? Cd1 N3 H3B 109.7 . . ? H3A N3 H3B 108.2 . . ? C7 N4 Cd1 109.9(7) . . ? C7 N4 H4A 109.7 . . ? Cd1 N4 H4A 109.7 . . ? C7 N4 H4B 109.7 . . ? Cd1 N4 H4B 109.7 . . ? H4A N4 H4B 108.2 . . ? C1 O1 Cd1 111.9(6) . . ? C1 O2 H2 109.5 . . ? C4 O4 Cd1 117.2(7) . 8_454 ? N1 Cd1 N3 135.0(3) . . ? N1 Cd1 N2 113.9(3) . 7_544 ? N3 Cd1 N2 110.7(3) . 7_544 ? N1 Cd1 N4 90.8(4) . . ? N3 Cd1 N4 74.3(3) . . ? N2 Cd1 N4 101.5(3) 7_544 . ? N1 Cd1 O4 97.7(3) . 7_544 ? N3 Cd1 O4 102.4(3) . 7_544 ? N2 Cd1 O4 70.8(3) 7_544 7_544 ? N4 Cd1 O4 170.3(3) . 7_544 ? N1 Cd1 O1 70.1(3) . . ? N3 Cd1 O1 78.7(3) . . ? N2 Cd1 O1 142.4(3) 7_544 . ? N4 Cd1 O1 116.0(3) . . ? O4 Cd1 O1 71.7(3) 7_544 . ? C2A C1A C6A 120.0(19) . . ? C2A C1A C5 121(2) . . ? C6A C1A C5 119.3(17) . . ? C1A C2A C3A 120(3) . . ? C1A C2A H2A 120.0 . . ? C3A C2A H2A 120.0 . . ? C4A C3A C2A 120(4) . . ? C4A C3A H3A1 120.0 . . ? C2A C3A H3A1 120.0 . . ? C3A C4A C5A 120(3) . . ? C3A C4A C7A 124(3) . . ? C5A C4A C7A 115(2) . . ? C4A C5A C6A 120(2) . . ? C4A C5A C8A 121.4(18) . . ? C6A C5A C8A 118.6(17) . . ? C5A C6A C1A 120.0(18) . . ? C5A C6A H6A1 120.0 . . ? C1A C6A H6A1 120.0 . . ? C4A C7A H7A1 109.5 . . ? C4A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C4A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C5A C8A H8A1 109.5 . . ? C5A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C5A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C2B C1B C6B 120.0(17) . . ? C2B C1B C5 123.2(17) . . ? C6B C1B C5 116.8(18) . . ? C1B C2B C3B 120.0(18) . . ? C1B C2B H2B 120.0 . . ? C3B C2B H2B 120.0 . . ? C4B C3B C2B 120.0(18) . . ? C4B C3B H3B1 120.0 . . ? C2B C3B H3B1 120.0 . . ? C3B C4B C5B 120(3) . . ? C3B C4B C7B 118.1(18) . . ? C5B C4B C7B 122(4) . . ? C6B C5B C4B 120(5) . . ? C6B C5B C8B 122(3) . . ? C4B C5B C8B 118(5) . . ? C5B C6B C1B 120(3) . . ? C5B C6B H6B1 120.0 . . ? C1B C6B H6B1 120.0 . . ? C4B C7B H7B1 109.5 . . ? C4B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C4B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C5B C8B H8B1 109.5 . . ? C5B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C5B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 174.4(10) . . . . ? O2 C1 C2 C3 -6.2(16) . . . . ? O1 C1 C2 N1 -2.4(15) . . . . ? O2 C1 C2 N1 177.0(9) . . . . ? N1 C2 C3 N2 -0.4(11) . . . . ? C1 C2 C3 N2 -177.4(10) . . . . ? N1 C2 C3 C4 178.2(10) . . . . ? C1 C2 C3 C4 1.2(18) . . . . ? N2 C3 C4 O4 -1.6(14) . . . . ? C2 C3 C4 O4 179.9(10) . . . . ? N2 C3 C4 O3 179.0(9) . . . . ? C2 C3 C4 O3 0.5(17) . . . . ? N3 C6 C7 N4 52.3(12) . . . . ? N2 C5 N1 C2 0.9(13) . . . . ? C1B C5 N1 C2 164.5(14) . . . . ? C1A C5 N1 C2 -160.0(16) . . . . ? N2 C5 N1 Cd1 171.4(8) . . . . ? C1B C5 N1 Cd1 -25(2) . . . . ? C1A C5 N1 Cd1 11(2) . . . . ? C3 C2 N1 C5 -0.3(12) . . . . ? C1 C2 N1 C5 177.3(9) . . . . ? C3 C2 N1 Cd1 -172.9(6) . . . . ? C1 C2 N1 Cd1 4.6(12) . . . . ? C2 C3 N2 C5 0.9(10) . . . . ? C4 C3 N2 C5 -177.9(9) . . . . ? C2 C3 N2 Cd1 -173.2(6) . . . 8_454 ? C4 C3 N2 Cd1 8.0(10) . . . 8_454 ? N1 C5 N2 C3 -1.1(12) . . . . ? C1B C5 N2 C3 -164.3(14) . . . . ? C1A C5 N2 C3 163.1(13) . . . . ? N1 C5 N2 Cd1 170.3(8) . . . 8_454 ? C1B C5 N2 Cd1 7(2) . . . 8_454 ? C1A C5 N2 Cd1 -25.4(19) . . . 8_454 ? C7 C6 N3 Cd1 -53.4(10) . . . . ? C6 C7 N4 Cd1 -24.9(11) . . . . ? O2 C1 O1 Cd1 179.9(8) . . . . ? C2 C1 O1 Cd1 -0.8(12) . . . . ? O3 C4 O4 Cd1 173.9(9) . . . 8_454 ? C3 C4 O4 Cd1 -5.5(13) . . . 8_454 ? C5 N1 Cd1 N3 -124.1(11) . . . . ? C2 N1 Cd1 N3 45.5(10) . . . . ? C5 N1 Cd1 N2 47.2(13) . . . 7_544 ? C2 N1 Cd1 N2 -143.1(7) . . . 7_544 ? C5 N1 Cd1 N4 -55.7(13) . . . . ? C2 N1 Cd1 N4 113.9(8) . . . . ? C5 N1 Cd1 O4 119.6(12) . . . 7_544 ? C2 N1 Cd1 O4 -70.8(8) . . . 7_544 ? C5 N1 Cd1 O1 -173.1(13) . . . . ? C2 N1 Cd1 O1 -3.5(7) . . . . ? C6 N3 Cd1 N1 104.3(7) . . . . ? C6 N3 Cd1 N2 -67.3(7) . . . 7_544 ? C6 N3 Cd1 N4 29.3(6) . . . . ? C6 N3 Cd1 O4 -141.2(6) . . . 7_544 ? C6 N3 Cd1 O1 150.7(7) . . . . ? C7 N4 Cd1 N1 -138.9(7) . . . . ? C7 N4 Cd1 N3 -1.9(7) . . . . ? C7 N4 Cd1 N2 106.6(7) . . . 7_544 ? C7 N4 Cd1 O4 70(2) . . . 7_544 ? C7 N4 Cd1 O1 -70.7(7) . . . . ? C1 O1 Cd1 N1 2.3(7) . . . . ? C1 O1 Cd1 N3 -144.8(8) . . . . ? C1 O1 Cd1 N2 105.9(7) . . . 7_544 ? C1 O1 Cd1 N4 -78.6(8) . . . . ? C1 O1 Cd1 O4 107.9(8) . . . 7_544 ? N1 C5 C1A C2A -101(2) . . . . ? N2 C5 C1A C2A 98(2) . . . . ? C1B C5 C1A C2A -18(2) . . . . ? N1 C5 C1A C6A 80(2) . . . . ? N2 C5 C1A C6A -81(2) . . . . ? C1B C5 C1A C6A 163(4) . . . . ? C6A C1A C2A C3A 0(5) . . . . ? C5 C1A C2A C3A -180(4) . . . . ? C1A C2A C3A C4A 0(8) . . . . ? C2A C3A C4A C5A 0(8) . . . . ? C2A C3A C4A C7A 171(4) . . . . ? C3A C4A C5A C6A 0(5) . . . . ? C7A C4A C5A C6A -171.9(18) . . . . ? C3A C4A C5A C8A -180(4) . . . . ? C7A C4A C5A C8A 8(3) . . . . ? C4A C5A C6A C1A 0(3) . . . . ? C8A C5A C6A C1A 179.8(19) . . . . ? C2A C1A C6A C5A 0(3) . . . . ? C5 C1A C6A C5A 179.7(17) . . . . ? N1 C5 C1B C2B -43(3) . . . . ? N2 C5 C1B C2B 118.9(19) . . . . ? C1A C5 C1B C2B -161(4) . . . . ? N1 C5 C1B C6B 136.6(17) . . . . ? N2 C5 C1B C6B -62(2) . . . . ? C1A C5 C1B C6B 18(2) . . . . ? C6B C1B C2B C3B 0(3) . . . . ? C5 C1B C2B C3B 179.5(17) . . . . ? C1B C2B C3B C4B 0(3) . . . . ? C2B C3B C4B C5B 0(5) . . . . ? C2B C3B C4B C7B 173.6(19) . . . . ? C3B C4B C5B C6B 0(8) . . . . ? C7B C4B C5B C6B -173(4) . . . . ? C3B C4B C5B C8B 178(4) . . . . ? C7B C4B C5B C8B 5(8) . . . . ? C4B C5B C6B C1B 0(8) . . . . ? C8B C5B C6B C1B -178(4) . . . . ? C2B C1B C6B C5B 0(5) . . . . ? C5 C1B C6B C5B -179(4) . . . . ? _diffrn_measured_fraction_theta_max 0.832 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.832 _refine_diff_density_max 1.224 _refine_diff_density_min -2.196 _refine_diff_density_rms 0.181 _database_code_depnum_ccdc_archive 'CCDC 937411' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H45.50 Cu3 N9 O12' _chemical_formula_weight 1203.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1070(16) _cell_length_b 13.386(2) _cell_length_c 18.061(3) _cell_angle_alpha 88.704(2) _cell_angle_beta 77.557(2) _cell_angle_gamma 81.910(2) _cell_volume 2596.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1231 _exptl_absorpt_coefficient_mu 1.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6981 _exptl_absorpt_correction_T_max 0.8818 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13137 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.1133 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.01 _reflns_number_total 8937 _reflns_number_gt 4939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+36.0987P] 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 8937 _refine_ls_number_parameters 723 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1631 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.2206 _refine_ls_wR_factor_gt 0.1952 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.4978(9) 0.0302(7) 0.6385(6) 0.033(2) Uani 1 1 d . . . C2 C 1.5030(10) -0.0733(8) 0.6107(6) 0.040(3) Uani 1 1 d . . . C3 C 1.1858(10) -0.1973(7) 0.6647(6) 0.037(2) Uani 1 1 d . . . H3 H 1.2386 -0.1807 0.6202 0.045 Uiso 1 1 calc R . . C4 C 1.1099(9) -0.2691(7) 0.6617(6) 0.037(2) Uani 1 1 d . . . H4A H 1.1116 -0.2995 0.6156 0.045 Uiso 1 1 calc R . . C5 C 1.0310(10) -0.2963(8) 0.7270(6) 0.037(2) Uani 1 1 d . . . H5 H 0.9793 -0.3450 0.7263 0.045 Uiso 1 1 calc R . . C6 C 1.0327(10) -0.2480(7) 0.7927(6) 0.037(2) Uani 1 1 d . . . H6 H 0.9821 -0.2650 0.8380 0.045 Uiso 1 1 calc R . . C7 C 1.1081(9) -0.1746(7) 0.7930(6) 0.037(2) Uani 1 1 d . . . H7 H 1.1044 -0.1413 0.8383 0.045 Uiso 1 1 calc R . . C8 C 1.2585(10) -0.0384(8) 0.9024(6) 0.041(3) Uani 1 1 d . . . C9 C 1.1639(9) 0.0335(7) 0.8777(5) 0.032(2) Uani 1 1 d . . . C10 C 1.0704(9) 0.1042(8) 0.9145(5) 0.032(2) Uani 1 1 d . . . C11 C 1.0275(9) 0.1303(8) 0.9959(6) 0.035(2) Uani 1 1 d . . . C12 C 1.0767(9) 0.1222(7) 0.7940(5) 0.031(2) Uani 1 1 d . . . C13 C 1.0614(10) 0.1657(9) 0.7209(6) 0.042(3) Uani 1 1 d . . . C14 C 1.0658(9) 0.1024(9) 0.6591(6) 0.042(3) Uani 1 1 d . A . H14 H 1.0796 0.0325 0.6627 0.050 Uiso 1 1 calc R . . C15 C 1.0481(10) 0.1511(9) 0.5909(6) 0.042(3) Uani 1 1 d . . . H15 H 1.0472 0.1118 0.5493 0.050 Uiso 0.58(2) 1 calc PR A 1 C16 C 1.0330(10) 0.2491(9) 0.5849(6) 0.042(3) Uani 1 1 d . A . C17 C 1.0319(10) 0.3082(9) 0.6441(6) 0.042(3) Uani 1 1 d . . . H17 H 1.0222 0.3779 0.6385 0.050 Uiso 1 1 calc R A 2 C18 C 1.0450(10) 0.2671(9) 0.7133(6) 0.042(3) Uani 1 1 d . A . H18 H 1.0427 0.3088 0.7543 0.050 Uiso 1 1 calc R . . C19 C 1.0160(17) 0.4193(14) 0.6313(10) 0.042(6) Uani 0.58(2) 1 d P A 1 H19A H 0.9956 0.4540 0.6793 0.063 Uiso 0.58(2) 1 calc PR A 1 H19B H 0.9501 0.4373 0.6047 0.063 Uiso 0.58(2) 1 calc PR A 1 H19C H 1.0921 0.4381 0.6017 0.063 Uiso 0.58(2) 1 calc PR A 1 C19' C 1.026(2) 0.087(2) 0.5278(14) 0.042(8) Uani 0.42(2) 1 d P A 2 H19D H 1.0425 0.1221 0.4806 0.063 Uiso 0.42(2) 1 calc PR A 2 H19E H 0.9410 0.0742 0.5390 0.063 Uiso 0.42(2) 1 calc PR A 2 H19F H 1.0804 0.0239 0.5239 0.063 Uiso 0.42(2) 1 calc PR A 2 C20 C 1.0131(10) 0.2956(8) 0.5077(6) 0.042(3) Uani 1 1 d . . . H20A H 0.9476 0.3517 0.5169 0.063 Uiso 1 1 calc R A . H20B H 0.9907 0.2454 0.4780 0.063 Uiso 1 1 calc R . . H20C H 1.0887 0.3181 0.4808 0.063 Uiso 1 1 calc R . . C21 C 0.7031(10) 0.3140(8) 1.0671(6) 0.039(3) Uani 1 1 d . . . H21 H 0.7782 0.2959 1.0822 0.047 Uiso 1 1 calc R . . C22 C 0.5993(9) 0.3599(8) 1.1195(6) 0.039(3) Uani 1 1 d . . . H22 H 0.6056 0.3741 1.1686 0.047 Uiso 1 1 calc R . . C23 C 0.4884(10) 0.3836(8) 1.0975(6) 0.039(3) Uani 1 1 d . . . H23 H 0.4186 0.4136 1.1320 0.047 Uiso 1 1 calc R . . C24 C 0.4793(10) 0.3638(8) 1.0258(6) 0.039(3) Uani 1 1 d . . . H24 H 0.4047 0.3800 1.0100 0.047 Uiso 1 1 calc R . . C25 C 0.5867(9) 0.3181(8) 0.9767(6) 0.039(3) Uani 1 1 d . . . H25 H 0.5807 0.3024 0.9279 0.047 Uiso 1 1 calc R . . C26 C 0.8373(9) 0.4405(8) 0.8461(6) 0.035(2) Uani 1 1 d . . . C27 C 0.7805(9) 0.3699(8) 0.8089(5) 0.035(2) Uani 1 1 d . . . C28 C 0.7283(9) 0.3798(7) 0.7454(6) 0.034(2) Uani 1 1 d . . . C29 C 0.7014(13) 0.4648(10) 0.6957(8) 0.059(4) Uani 1 1 d . . . C30 C 0.7314(9) 0.2255(8) 0.7817(6) 0.036(2) Uani 1 1 d . . . C31 C 0.7259(9) 0.1149(8) 0.7826(6) 0.036(2) Uani 1 1 d . . . C32 C 0.7618(9) 0.0615(8) 0.7163(6) 0.036(2) Uani 1 1 d . . . H32 H 0.7912 0.0941 0.6713 0.043 Uiso 1 1 calc R . . C33 C 0.7549(9) -0.0398(8) 0.7154(6) 0.036(2) Uani 1 1 d . . . H33 H 0.7848 -0.0763 0.6705 0.043 Uiso 1 1 calc R . . C34 C 0.7037(9) -0.0882(8) 0.7806(6) 0.036(2) Uani 1 1 d . . . C35 C 0.6651(9) -0.0349(8) 0.8474(6) 0.036(2) Uani 1 1 d . . . C36 C 0.6782(9) 0.0674(7) 0.8498(6) 0.036(2) Uani 1 1 d . . . H36 H 0.6555 0.1031 0.8954 0.043 Uiso 1 1 calc R . . C37 C 0.6166(9) -0.0912(8) 0.9148(6) 0.036(2) Uani 1 1 d . . . H37A H 0.6045 -0.0493 0.9589 0.054 Uiso 1 1 calc R . . H37B H 0.6749 -0.1501 0.9190 0.054 Uiso 1 1 calc R . . H37C H 0.5386 -0.1112 0.9108 0.054 Uiso 1 1 calc R . . C38 C 0.6889(9) -0.1989(7) 0.7783(6) 0.036(2) Uani 1 1 d . . . H38A H 0.6646 -0.2133 0.7323 0.054 Uiso 1 1 calc R . . H38B H 0.6262 -0.2140 0.8210 0.054 Uiso 1 1 calc R . . H38C H 0.7666 -0.2395 0.7803 0.054 Uiso 1 1 calc R . . C39 C 0.4223(11) 0.4693(8) 0.5963(6) 0.046(3) Uani 1 1 d . . . H39 H 0.4480 0.5089 0.6301 0.055 Uiso 1 1 calc R . . C40 C 0.3341(11) 0.5136(9) 0.5556(6) 0.046(3) Uani 1 1 d . . . H40 H 0.3046 0.5822 0.5607 0.055 Uiso 1 1 calc R . . C41 C 0.2923(11) 0.4546(8) 0.5083(6) 0.046(3) Uani 1 1 d . . . H41 H 0.2325 0.4826 0.4820 0.055 Uiso 1 1 calc R . . C42 C 0.3381(11) 0.3554(8) 0.4998(6) 0.046(3) Uani 1 1 d . . . H42 H 0.3113 0.3145 0.4674 0.055 Uiso 1 1 calc R . . C43 C 0.4256(11) 0.3165(9) 0.5404(6) 0.046(3) Uani 1 1 d . . . H43 H 0.4561 0.2481 0.5351 0.055 Uiso 1 1 calc R . . C44 C 0.6635(10) 0.1173(9) 0.5465(6) 0.041(3) Uani 1 1 d . . . C45 C 0.5617(9) 0.1081(8) 0.6135(6) 0.036(2) Uani 1 1 d . . . C46 C 0.4330(9) 0.1533(7) 0.7170(5) 0.029(2) Uani 1 1 d . . . C47 C 0.3671(9) 0.2186(8) 0.7838(6) 0.034(2) Uani 1 1 d . . . C48 C 0.3094(9) 0.3163(7) 0.7710(6) 0.034(2) Uani 1 1 d . . . H48 H 0.3148 0.3397 0.7217 0.040 Uiso 1 1 calc R . . C49 C 0.2447(9) 0.3774(7) 0.8317(6) 0.034(2) Uani 1 1 d . . . C50 C 0.2351(9) 0.3419(7) 0.9049(6) 0.034(2) Uani 1 1 d . . . C51 C 0.2950(9) 0.2459(7) 0.9164(6) 0.034(2) Uani 1 1 d . . . H51 H 0.2892 0.2220 0.9656 0.040 Uiso 1 1 calc R . . C52 C 0.3628(9) 0.1851(8) 0.8564(5) 0.034(2) Uani 1 1 d . . . H52 H 0.4049 0.1223 0.8653 0.040 Uiso 1 1 calc R . . C53 C 0.1614(9) 0.4038(7) 0.9727(5) 0.034(2) Uani 1 1 d . . . H53A H 0.0766 0.4207 0.9678 0.051 Uiso 1 1 calc R . . H53B H 0.1970 0.4647 0.9754 0.051 Uiso 1 1 calc R . . H53C H 0.1638 0.3656 1.0181 0.051 Uiso 1 1 calc R . . C54 C 0.1793(9) 0.4811(7) 0.8154(6) 0.034(2) Uani 1 1 d . . . H54A H 0.0935 0.4768 0.8160 0.051 Uiso 1 1 calc R . . H54B H 0.2191 0.5033 0.7664 0.051 Uiso 1 1 calc R . . H54C H 0.1841 0.5284 0.8534 0.051 Uiso 1 1 calc R . . N1 N 1.4147(7) 0.0594(6) 0.7042(5) 0.0314(19) Uani 1 1 d . . . N2 N 1.1868(8) -0.1495(6) 0.7300(5) 0.037(2) Uani 1 1 d . . . N3 N 1.1683(7) 0.0442(6) 0.8003(4) 0.0310(19) Uani 1 1 d . . . N4 N 1.0152(7) 0.1592(6) 0.8628(4) 0.0304(18) Uani 1 1 d . . . N5 N 0.6960(8) 0.2956(7) 0.9948(5) 0.039(2) Uani 1 1 d . . . N6 N 0.7810(7) 0.2713(6) 0.8318(4) 0.0288(18) Uani 1 1 d . . . N7 N 0.6974(8) 0.2880(6) 0.7296(5) 0.035(2) Uani 1 1 d . . . N8 N 0.5220(7) 0.1855(6) 0.6630(4) 0.0302(18) Uani 1 1 d . . . N9 N 0.4696(9) 0.3723(7) 0.5878(5) 0.046(2) Uani 1 1 d . . . O1 O 1.5802(7) -0.1055(6) 0.5530(5) 0.055(2) Uani 1 1 d . . . O2 O 1.4257(7) -0.1237(5) 0.6522(4) 0.0436(19) Uani 1 1 d . . . O3 O 1.3346(7) -0.0935(5) 0.8547(4) 0.0428(18) Uani 1 1 d . . . O4 O 1.2597(8) -0.0410(6) 0.9741(4) 0.050(2) Uani 1 1 d . . . H4 H 1.2051 0.0020 0.9968 0.076 Uiso 1 1 calc R . . O5 O 1.0823(7) 0.0920(6) 1.0430(4) 0.047(2) Uani 1 1 d . . . O6 O 0.9332(6) 0.1993(6) 1.0078(4) 0.047(2) Uani 1 1 d . . . O7 O 0.8882(7) 0.4122(6) 0.8970(4) 0.0476(19) Uani 1 1 d . . . O8 O 0.8332(8) 0.5330(5) 0.8213(5) 0.051(2) Uani 1 1 d . . . H8 H 0.8141 0.5356 0.7798 0.077 Uiso 1 1 calc R . . O9 O 0.7304(9) 0.5488(6) 0.7069(6) 0.070(3) Uani 1 1 d . . . O10 O 0.6540(9) 0.4428(6) 0.6424(5) 0.066(3) Uani 1 1 d . . . O11 O 0.7079(7) 0.1970(6) 0.5365(4) 0.052(2) Uani 1 1 d . . . O12 O 0.7033(8) 0.0413(6) 0.4992(4) 0.052(2) Uani 1 1 d . . . H12 H 0.6900 -0.0114 0.5214 0.078 Uiso 1 1 calc R . . Cu1 Cu 0.85720(11) 0.23792(10) 0.92085(7) 0.0339(3) Uani 1 1 d . . . Cu2 Cu 1.29973(11) -0.04399(9) 0.73159(7) 0.0321(3) Uani 1 1 d . . . Cu3 Cu 0.59393(13) 0.31106(10) 0.64886(7) 0.0388(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.027(5) 0.032(6) 0.038(6) -0.011(4) -0.005(4) 0.000(4) C2 0.040(6) 0.031(6) 0.052(7) -0.001(5) -0.016(6) -0.007(5) C3 0.040(6) 0.034(6) 0.035(6) -0.007(5) -0.002(5) -0.003(5) C4 0.040(6) 0.034(6) 0.035(6) -0.007(5) -0.002(5) -0.003(5) C5 0.040(6) 0.034(6) 0.035(6) -0.007(5) -0.002(5) -0.003(5) C6 0.040(6) 0.034(6) 0.035(6) -0.007(5) -0.002(5) -0.003(5) C7 0.040(6) 0.034(6) 0.035(6) -0.007(5) -0.002(5) -0.003(5) C8 0.034(6) 0.041(7) 0.048(7) 0.009(5) -0.012(5) -0.007(5) C9 0.033(6) 0.032(6) 0.031(5) -0.002(4) -0.010(4) -0.005(4) C10 0.031(5) 0.043(6) 0.023(5) -0.004(4) -0.008(4) -0.009(5) C11 0.024(5) 0.052(7) 0.028(6) -0.008(5) 0.004(4) -0.014(5) C12 0.026(5) 0.035(6) 0.028(5) -0.007(4) -0.005(4) 0.003(4) C13 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C14 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C15 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C16 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C17 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C18 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C19 0.035(11) 0.053(13) 0.037(11) 0.002(9) -0.009(9) -0.003(9) C19' 0.035(15) 0.053(17) 0.037(15) 0.002(12) -0.009(12) -0.003(12) C20 0.035(6) 0.053(7) 0.037(6) 0.002(5) -0.009(5) -0.003(5) C21 0.033(6) 0.043(6) 0.041(6) -0.007(5) -0.008(5) -0.001(5) C22 0.033(6) 0.043(6) 0.041(6) -0.007(5) -0.008(5) -0.001(5) C23 0.033(6) 0.043(6) 0.041(6) -0.007(5) -0.008(5) -0.001(5) C24 0.033(6) 0.043(6) 0.041(6) -0.007(5) -0.008(5) -0.001(5) C25 0.033(6) 0.043(6) 0.041(6) -0.007(5) -0.008(5) -0.001(5) C26 0.023(5) 0.034(6) 0.048(7) -0.017(5) -0.005(5) 0.000(4) C27 0.029(5) 0.045(6) 0.031(6) -0.010(5) -0.008(4) -0.007(5) C28 0.037(6) 0.024(5) 0.043(6) 0.003(4) -0.014(5) -0.003(4) C29 0.072(9) 0.053(8) 0.067(9) 0.023(7) -0.027(7) -0.037(7) C30 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C31 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C32 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C33 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C34 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C35 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(5) C36 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C37 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C38 0.027(5) 0.037(6) 0.043(6) -0.004(5) -0.007(5) -0.004(4) C39 0.054(7) 0.042(7) 0.043(7) 0.003(5) -0.016(6) -0.002(6) C40 0.054(7) 0.042(7) 0.043(7) 0.003(5) -0.016(6) -0.002(6) C41 0.054(7) 0.042(7) 0.043(7) 0.003(5) -0.016(6) -0.002(6) C42 0.054(7) 0.042(7) 0.043(7) 0.003(5) -0.016(6) -0.002(6) C43 0.054(7) 0.042(7) 0.043(7) 0.003(5) -0.016(6) -0.002(6) C44 0.039(6) 0.051(7) 0.035(6) 0.002(5) -0.007(5) -0.009(5) C45 0.034(6) 0.034(6) 0.036(6) 0.002(5) -0.003(5) -0.003(5) C46 0.030(5) 0.030(5) 0.027(5) 0.001(4) -0.007(4) -0.004(4) C47 0.032(6) 0.036(6) 0.034(6) -0.007(4) -0.004(4) -0.010(5) C48 0.032(5) 0.036(6) 0.034(6) -0.007(4) -0.004(4) -0.010(5) C49 0.032(6) 0.036(6) 0.034(6) -0.007(5) -0.004(5) -0.010(5) C50 0.032(6) 0.036(6) 0.034(6) -0.007(5) -0.004(4) -0.010(5) C51 0.032(6) 0.036(6) 0.034(6) -0.007(5) -0.004(4) -0.010(5) C52 0.032(6) 0.036(6) 0.034(6) -0.007(5) -0.004(4) -0.010(5) C53 0.032(6) 0.036(6) 0.034(6) -0.007(4) -0.004(4) -0.010(5) C54 0.032(6) 0.036(6) 0.034(6) -0.007(4) -0.004(4) -0.010(5) N1 0.026(4) 0.026(4) 0.039(5) -0.007(4) -0.001(4) -0.005(3) N2 0.040(5) 0.034(5) 0.035(5) -0.007(4) -0.002(4) -0.003(4) N3 0.036(5) 0.031(5) 0.027(4) -0.004(3) -0.007(4) -0.008(4) N4 0.029(4) 0.033(5) 0.028(4) -0.006(4) -0.007(4) 0.006(4) N5 0.033(5) 0.043(5) 0.041(5) -0.007(4) -0.008(4) -0.001(4) N6 0.024(4) 0.028(4) 0.038(5) -0.008(4) -0.013(4) -0.003(3) N7 0.039(5) 0.026(4) 0.044(5) 0.003(4) -0.016(4) -0.012(4) N8 0.032(5) 0.030(5) 0.031(5) 0.000(4) -0.010(4) -0.007(4) N9 0.054(6) 0.042(6) 0.043(6) 0.003(4) -0.016(5) -0.002(5) O1 0.044(5) 0.049(5) 0.059(5) -0.025(4) 0.020(4) -0.006(4) O2 0.040(4) 0.030(4) 0.054(5) -0.013(3) 0.008(4) -0.003(3) O3 0.037(4) 0.041(4) 0.049(5) -0.004(4) -0.011(4) 0.000(3) O4 0.060(6) 0.051(5) 0.041(5) -0.001(4) -0.021(4) 0.008(4) O5 0.042(4) 0.079(6) 0.019(4) 0.006(4) -0.011(3) -0.002(4) O6 0.031(4) 0.072(6) 0.033(4) -0.019(4) -0.004(3) 0.006(4) O7 0.050(5) 0.046(5) 0.052(5) -0.016(4) -0.019(4) -0.009(4) O8 0.051(5) 0.032(4) 0.076(6) -0.005(4) -0.018(5) -0.014(4) O9 0.083(7) 0.044(5) 0.104(8) 0.024(5) -0.050(6) -0.034(5) O10 0.111(8) 0.050(5) 0.060(6) 0.028(4) -0.049(6) -0.041(5) O11 0.052(5) 0.048(5) 0.050(5) -0.004(4) 0.012(4) -0.022(4) O12 0.048(5) 0.051(5) 0.049(5) -0.007(4) 0.012(4) -0.011(4) Cu1 0.0264(7) 0.0435(8) 0.0312(7) -0.0076(6) -0.0063(5) -0.0006(5) Cu2 0.0310(7) 0.0281(7) 0.0348(7) -0.0060(5) -0.0002(5) -0.0055(5) Cu3 0.0494(8) 0.0355(7) 0.0381(7) 0.0071(6) -0.0179(6) -0.0161(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C45 1.358(13) 1_655 ? C1 N1 1.363(12) . ? C1 C2 1.474(13) . ? C2 O1 1.240(12) . ? C2 O2 1.272(12) . ? C3 N2 1.357(12) . ? C3 C4 1.374(14) . ? C3 H3 0.9300 . ? C4 C5 1.385(14) . ? C4 H4A 0.9300 . ? C5 C6 1.370(13) . ? C5 H5 0.9300 . ? C6 C7 1.379(14) . ? C6 H6 0.9300 . ? C7 N2 1.346(12) . ? C7 H7 0.9300 . ? C8 O3 1.241(12) . ? C8 O4 1.298(12) . ? C8 C9 1.458(14) . ? C9 C10 1.368(13) . ? C9 N3 1.393(12) . ? C10 N4 1.370(12) . ? C10 C11 1.477(13) . ? C11 O5 1.215(12) . ? C11 O6 1.279(12) . ? C12 N4 1.351(11) . ? C12 N3 1.373(12) . ? C12 C13 1.464(14) . ? C13 C18 1.352(15) . ? C13 C14 1.404(15) . ? C14 C15 1.418(14) . ? C14 H14 0.9300 . ? C15 C16 1.305(15) . ? C15 C19' 1.53(3) . ? C15 H15 0.9300 . ? C16 C17 1.342(15) . ? C16 C20 1.559(14) . ? C17 C18 1.383(14) . ? C17 C19 1.49(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C19' H19D 0.9600 . ? C19' H19E 0.9600 . ? C19' H19F 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 N5 1.356(13) . ? C21 C22 1.400(14) . ? C21 H21 0.9300 . ? C22 C23 1.368(14) . ? C22 H22 0.9300 . ? C23 C24 1.355(14) . ? C23 H23 0.9300 . ? C24 C25 1.395(14) . ? C24 H24 0.9300 . ? C25 N5 1.317(13) . ? C25 H25 0.9300 . ? C26 O7 1.207(12) . ? C26 O8 1.305(12) . ? C26 C27 1.457(13) . ? C27 N6 1.374(12) . ? C27 C28 1.388(13) . ? C28 N7 1.373(12) . ? C28 C29 1.470(15) . ? C29 O9 1.245(13) . ? C29 O10 1.252(14) . ? C30 N7 1.325(13) . ? C30 N6 1.353(12) . ? C30 C31 1.490(14) . ? C31 C32 1.363(14) . ? C31 C36 1.393(14) . ? C32 C33 1.369(14) . ? C32 H32 0.9300 . ? C33 C34 1.383(14) . ? C33 H33 0.9300 . ? C34 C35 1.370(14) . ? C34 C38 1.516(13) . ? C35 C36 1.401(13) . ? C35 C37 1.458(14) . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 N9 1.330(13) . ? C39 C40 1.407(15) . ? C39 H39 0.9300 . ? C40 C41 1.369(15) . ? C40 H40 0.9300 . ? C41 C42 1.353(15) . ? C41 H41 0.9300 . ? C42 C43 1.379(15) . ? C42 H42 0.9300 . ? C43 N9 1.357(13) . ? C43 H43 0.9300 . ? C44 O11 1.231(12) . ? C44 O12 1.308(13) . ? C44 C45 1.484(14) . ? C45 N8 1.346(12) . ? C45 C1 1.358(13) 1_455 ? C46 N1 1.335(11) 1_455 ? C46 N8 1.342(12) . ? C46 C47 1.497(13) . ? C47 C52 1.369(14) . ? C47 C48 1.410(14) . ? C48 C49 1.388(13) . ? C48 H48 0.9300 . ? C49 C50 1.382(14) . ? C49 C54 1.527(14) . ? C50 C51 1.394(14) . ? C50 C53 1.510(13) . ? C51 C52 1.386(13) . ? C51 H51 0.9300 . ? C52 H52 0.9300 . ? C53 H53A 0.9600 . ? C53 H53B 0.9600 . ? C53 H53C 0.9600 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? N1 C46 1.335(11) 1_655 ? N1 Cu2 1.996(7) . ? N2 Cu2 2.021(8) . ? N3 Cu2 1.965(8) . ? N4 Cu1 2.006(7) . ? N5 Cu1 2.052(8) . ? N6 Cu1 1.988(8) . ? N7 Cu3 2.036(8) . ? N8 Cu3 1.949(8) . ? N9 Cu3 2.023(9) . ? O2 Cu2 1.985(7) . ? O3 Cu2 2.401(7) . ? O4 H4 0.8200 . ? O6 Cu1 1.964(7) . ? O7 Cu1 2.422(8) . ? O8 H8 0.8200 . ? O10 Cu3 1.965(8) . ? O12 H12 0.8200 . ? 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 C45 C1 N1 108.4(8) 1_655 . ? C45 C1 C2 133.8(9) 1_655 . ? N1 C1 C2 117.7(9) . . ? O1 C2 O2 125.5(10) . . ? O1 C2 C1 120.6(10) . . ? O2 C2 C1 113.8(9) . . ? N2 C3 C4 122.7(10) . . ? N2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C3 C4 C5 120.2(10) . . ? C3 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C6 C5 C4 116.8(10) . . ? C6 C5 H5 121.6 . . ? C4 C5 H5 121.6 . . ? C5 C6 C7 121.1(10) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? N2 C7 C6 122.2(9) . . ? N2 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? O3 C8 O4 122.7(10) . . ? O3 C8 C9 119.4(10) . . ? O4 C8 C9 117.9(10) . . ? C10 C9 N3 107.4(8) . . ? C10 C9 C8 133.7(9) . . ? N3 C9 C8 118.7(9) . . ? C9 C10 N4 109.8(8) . . ? C9 C10 C11 131.1(9) . . ? N4 C10 C11 119.0(9) . . ? O5 C11 O6 126.4(9) . . ? O5 C11 C10 121.6(10) . . ? O6 C11 C10 111.9(9) . . ? N4 C12 N3 111.2(8) . . ? N4 C12 C13 125.7(9) . . ? N3 C12 C13 122.6(8) . . ? C18 C13 C14 120.5(10) . . ? C18 C13 C12 119.3(10) . . ? C14 C13 C12 120.1(10) . . ? C13 C14 C15 116.3(10) . . ? C13 C14 H14 121.9 . . ? C15 C14 H14 121.9 . . ? C16 C15 C14 122.1(11) . . ? C16 C15 C19' 119.2(13) . . ? C14 C15 C19' 118.0(14) . . ? C16 C15 H15 119.0 . . ? C14 C15 H15 119.0 . . ? C19' C15 H15 8.6 . . ? C15 C16 C17 120.7(11) . . ? C15 C16 C20 118.3(10) . . ? C17 C16 C20 121.1(10) . . ? C16 C17 C18 121.1(11) . . ? C16 C17 C19 116.8(12) . . ? C18 C17 C19 122.2(12) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C17 H17 2.7 . . ? C13 C18 C17 119.3(11) . . ? C13 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? C15 C19' H19D 109.5 . . ? C15 C19' H19E 109.5 . . ? H19D C19' H19E 109.5 . . ? C15 C19' H19F 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N5 C21 C22 121.0(10) . . ? N5 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 119.1(10) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 120.5(10) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 117.2(10) . . ? C23 C24 H24 121.4 . . ? C25 C24 H24 121.4 . . ? N5 C25 C24 124.6(10) . . ? N5 C25 H25 117.7 . . ? C24 C25 H25 117.7 . . ? O7 C26 O8 122.2(9) . . ? O7 C26 C27 120.0(10) . . ? O8 C26 C27 117.8(10) . . ? N6 C27 C28 107.1(8) . . ? N6 C27 C26 121.3(9) . . ? C28 C27 C26 131.4(10) . . ? N7 C28 C27 108.6(8) . . ? N7 C28 C29 117.7(9) . . ? C27 C28 C29 133.6(10) . . ? O9 C29 O10 125.5(11) . . ? O9 C29 C28 120.0(11) . . ? O10 C29 C28 114.4(10) . . ? N7 C30 N6 112.8(9) . . ? N7 C30 C31 124.4(9) . . ? N6 C30 C31 122.6(9) . . ? C32 C31 C36 120.2(10) . . ? C32 C31 C30 119.3(10) . . ? C36 C31 C30 120.4(9) . . ? C31 C32 C33 120.4(10) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C32 C33 C34 120.7(10) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C35 C34 C33 119.4(10) . . ? C35 C34 C38 120.1(9) . . ? C33 C34 C38 120.5(9) . . ? C34 C35 C36 120.4(10) . . ? C34 C35 C37 116.8(9) . . ? C36 C35 C37 122.8(9) . . ? C31 C36 C35 118.9(10) . . ? C31 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N9 C39 C40 121.6(11) . . ? N9 C39 H39 119.2 . . ? C40 C39 H39 119.2 . . ? C41 C40 C39 119.2(11) . . ? C41 C40 H40 120.4 . . ? C39 C40 H40 120.4 . . ? C42 C41 C40 120.0(11) . . ? C42 C41 H41 120.0 . . ? C40 C41 H41 120.0 . . ? C41 C42 C43 118.2(11) . . ? C41 C42 H42 120.9 . . ? C43 C42 H42 120.9 . . ? N9 C43 C42 123.7(11) . . ? N9 C43 H43 118.1 . . ? C42 C43 H43 118.1 . . ? O11 C44 O12 121.5(10) . . ? O11 C44 C45 118.9(10) . . ? O12 C44 C45 119.5(10) . . ? N8 C45 C1 108.9(9) . 1_455 ? N8 C45 C44 119.6(9) . . ? C1 C45 C44 131.4(10) 1_455 . ? N1 C46 N8 112.5(8) 1_455 . ? N1 C46 C47 126.2(8) 1_455 . ? N8 C46 C47 121.3(8) . . ? C52 C47 C48 120.0(9) . . ? C52 C47 C46 121.1(9) . . ? C48 C47 C46 118.8(9) . . ? C49 C48 C47 120.1(10) . . ? C49 C48 H48 119.9 . . ? C47 C48 H48 119.9 . . ? C50 C49 C48 119.9(10) . . ? C50 C49 C54 121.5(9) . . ? C48 C49 C54 118.5(9) . . ? C49 C50 C51 119.0(9) . . ? C49 C50 C53 121.9(9) . . ? C51 C50 C53 119.1(9) . . ? C52 C51 C50 121.7(10) . . ? C52 C51 H51 119.2 . . ? C50 C51 H51 119.2 . . ? C47 C52 C51 119.1(10) . . ? C47 C52 H52 120.4 . . ? C51 C52 H52 120.4 . . ? C50 C53 H53A 109.5 . . ? C50 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C50 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C49 C54 H54A 109.5 . . ? C49 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C49 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C46 N1 C1 104.9(8) 1_655 . ? C46 N1 Cu2 145.1(7) 1_655 . ? C1 N1 Cu2 108.8(6) . . ? C7 N2 C3 116.9(9) . . ? C7 N2 Cu2 121.8(7) . . ? C3 N2 Cu2 121.3(7) . . ? C12 N3 C9 105.7(8) . . ? C12 N3 Cu2 137.3(6) . . ? C9 N3 Cu2 116.9(6) . . ? C12 N4 C10 105.9(8) . . ? C12 N4 Cu1 144.9(6) . . ? C10 N4 Cu1 107.2(6) . . ? C25 N5 C21 117.6(9) . . ? C25 N5 Cu1 124.8(7) . . ? C21 N5 Cu1 117.6(7) . . ? C30 N6 C27 105.8(8) . . ? C30 N6 Cu1 139.8(7) . . ? C27 N6 Cu1 114.3(6) . . ? C30 N7 C28 105.6(8) . . ? C30 N7 Cu3 145.8(7) . . ? C28 N7 Cu3 107.3(6) . . ? C46 N8 C45 105.2(8) . . ? C46 N8 Cu3 133.0(7) . . ? C45 N8 Cu3 121.8(7) . . ? C39 N9 C43 117.2(10) . . ? C39 N9 Cu3 120.3(8) . . ? C43 N9 Cu3 122.3(8) . . ? C2 O2 Cu2 115.0(6) . . ? C8 O3 Cu2 107.7(7) . . ? C8 O4 H4 109.5 . . ? C11 O6 Cu1 116.5(6) . . ? C26 O7 Cu1 106.9(6) . . ? C26 O8 H8 109.5 . . ? C29 O10 Cu3 116.0(7) . . ? C44 O12 H12 109.5 . . ? O6 Cu1 N6 177.7(3) . . ? O6 Cu1 N4 82.6(3) . . ? N6 Cu1 N4 96.1(3) . . ? O6 Cu1 N5 89.2(3) . . ? N6 Cu1 N5 91.8(3) . . ? N4 Cu1 N5 168.8(3) . . ? O6 Cu1 O7 104.8(3) . . ? N6 Cu1 O7 77.3(3) . . ? N4 Cu1 O7 103.9(3) . . ? N5 Cu1 O7 85.5(3) . . ? N3 Cu2 O2 173.1(3) . . ? N3 Cu2 N1 95.8(3) . . ? O2 Cu2 N1 82.4(3) . . ? N3 Cu2 N2 92.3(3) . . ? O2 Cu2 N2 88.1(3) . . ? N1 Cu2 N2 165.1(3) . . ? N3 Cu2 O3 77.1(3) . . ? O2 Cu2 O3 109.8(3) . . ? N1 Cu2 O3 101.0(3) . . ? N2 Cu2 O3 92.9(3) . . ? N8 Cu3 O10 174.7(4) . . ? N8 Cu3 N9 92.4(4) . . ? O10 Cu3 N9 86.8(4) . . ? N8 Cu3 N7 97.4(3) . . ? O10 Cu3 N7 82.1(3) . . ? N9 Cu3 N7 162.5(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O5 0.82 1.76 2.580(11) 177.1 . O8 H8 O9 0.82 1.76 2.559(12) 163.7 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.354 _refine_diff_density_min -2.547 _refine_diff_density_rms 0.172 _database_code_depnum_ccdc_archive 'CCDC 937412' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 N4 O10 Pb4' _chemical_formula_weight 1377.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 6.91220(10) _cell_length_b 13.2192(3) _cell_length_c 16.6432(4) _cell_angle_alpha 69.1940(10) _cell_angle_beta 86.754(2) _cell_angle_gamma 79.3670(10) _cell_volume 1397.11(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3283 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.20 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 24.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0520 _exptl_absorpt_correction_T_max 0.1967 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7574 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4842 _reflns_number_gt 4035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1366P)^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 4842 _refine_ls_number_parameters 395 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pb1 Pb 0.05101(11) 0.22350(5) 1.16701(5) 0.0247(2) Uani 1 1 d . . . Pb2 Pb 0.37814(9) 0.28568(5) 0.82024(4) 0.0223(2) Uani 1 1 d . . . Pb3 Pb 0.64596(9) 0.10232(5) 1.04305(5) 0.0231(2) Uani 1 1 d . . . Pb4 Pb -0.14157(9) 0.39373(5) 0.93619(5) 0.0237(2) Uani 1 1 d . . . N1 N -0.012(2) 0.0243(10) 1.2136(10) 0.023(3) Uani 1 1 d . . . N2 N -0.148(2) -0.1227(10) 1.2243(10) 0.023(3) Uani 1 1 d . . . N3 N 0.685(2) 0.6072(11) 0.7816(10) 0.022(3) Uani 1 1 d . . . N4 N 0.501(2) 0.4816(11) 0.7828(10) 0.022(3) Uani 1 1 d . . . O1 O 0.4103(17) -0.0434(9) 1.0904(8) 0.027(3) Uani 1 1 d . . . O2 O 0.3324(16) 0.0884(8) 1.1430(8) 0.020(3) Uani 1 1 d . . . O3 O 0.2568(16) -0.2313(8) 1.1132(8) 0.020(3) Uani 1 1 d . . . O4 O -0.0270(17) -0.2832(8) 1.1523(7) 0.020(3) Uani 1 1 d . . . O5 O 0.1795(17) 0.4226(9) 0.8811(8) 0.024(3) Uani 1 1 d . . . O6 O 0.1281(17) 0.5689(8) 0.9197(8) 0.023(3) Uani 1 1 d . . . O7 O 0.3574(19) 0.7455(10) 0.8939(10) 0.040(4) Uani 1 1 d . . . O8 O 0.6785(18) 0.6781(9) 0.9228(9) 0.030(3) Uani 1 1 d . . . O9 O 0.3861(17) 0.2134(9) 0.9637(8) 0.029(3) Uani 1 1 d . . . H9A H 0.2774 0.1733 0.9801 0.035 Uiso 1 1 calc R . . H9B H 0.3536 0.2750 0.9837 0.035 Uiso 1 1 calc R . . O10 O 0.0013(17) 0.2286(8) 1.0322(9) 0.027 Uani 1 1 d . . . C1 C 0.291(2) 0.0039(12) 1.1333(11) 0.021(4) Uani 1 1 d . . . C2 C 0.112(2) -0.0362(12) 1.1738(12) 0.021(4) Uani 1 1 d . . . C3 C 0.025(3) -0.1250(13) 1.1769(13) 0.024(4) Uani 1 1 d . . . C4 C 0.089(2) -0.2172(12) 1.1465(12) 0.019(4) Uani 1 1 d . . . C5 C -0.162(3) -0.0282(13) 1.2440(12) 0.023(4) Uani 1 1 d . . . C6 C -0.319(3) 0.0056(13) 1.2964(11) 0.023(4) Uani 1 1 d . . . C7 C -0.302(3) 0.0885(13) 1.3275(11) 0.024(4) Uani 1 1 d . . . H7 H -0.1871 0.1178 1.3171 0.029 Uiso 1 1 calc R . . C8 C -0.450(3) 0.1291(13) 1.3730(12) 0.024(4) Uani 1 1 d . . . C9 C -0.619(3) 0.0807(13) 1.3926(11) 0.024(4) Uani 1 1 d . . . C10 C -0.637(3) -0.0073(13) 1.3687(11) 0.024(4) Uani 1 1 d . . . H10B H -0.7469 -0.0411 1.3847 0.037 Uiso 1 1 calc R . . C11 C -0.483(3) -0.0457(13) 1.3185(11) 0.024(4) Uani 1 1 d . . . H11 H -0.4937 -0.1041 1.3012 0.029 Uiso 1 1 calc R . . C12 C -0.419(3) 0.2192(13) 1.4087(11) 0.025(4) Uani 1 1 d . . . H12A H -0.4187 0.1898 1.4704 0.037 Uiso 1 1 calc R . . H12B H -0.5237 0.2811 1.3886 0.037 Uiso 1 1 calc R . . H12C H -0.2952 0.2420 1.3891 0.037 Uiso 1 1 calc R . . C13 C -0.794(3) 0.1248(13) 1.4408(11) 0.025(4) Uani 1 1 d . . . H13A H -0.9124 0.1048 1.4280 0.037 Uiso 1 1 calc R . . H13B H -0.8098 0.2034 1.4225 0.037 Uiso 1 1 calc R . . H13C H -0.7687 0.0933 1.5016 0.037 Uiso 1 1 calc R . . C14 C 0.231(2) 0.5107(13) 0.8814(12) 0.022(4) Uani 1 1 d . . . C15 C 0.410(2) 0.5400(13) 0.8319(12) 0.022(4) Uani 1 1 d . . . C16 C 0.530(2) 0.6176(13) 0.8281(12) 0.022(4) Uani 1 1 d . . . C17 C 0.514(2) 0.6891(13) 0.8827(12) 0.022(4) Uani 1 1 d . . . C18 C 0.660(2) 0.5226(13) 0.7549(12) 0.022(4) Uani 1 1 d . . . C19 C 0.810(2) 0.4870(13) 0.6969(12) 0.023(4) Uani 1 1 d . . . C20 C 0.779(3) 0.4080(13) 0.6630(12) 0.023(4) Uani 1 1 d . . . H20 H 0.6600 0.3831 0.6725 0.027 Uiso 1 1 calc R . . C21 C 0.923(2) 0.3661(13) 0.6154(12) 0.023(4) Uani 1 1 d . . . C22 C 1.105(2) 0.4041(13) 0.6021(12) 0.023(4) Uani 1 1 d . . . C23 C 1.134(2) 0.4869(13) 0.6296(12) 0.023(4) Uani 1 1 d . . . H23 H 1.2481 0.5174 0.6151 0.027 Uiso 1 1 calc R . . C24 C 0.986(2) 0.5254(13) 0.6810(12) 0.023(4) Uani 1 1 d . . . H24 H 1.0085 0.5769 0.7039 0.027 Uiso 1 1 calc R . . C25 C 0.883(2) 0.2788(13) 0.5817(12) 0.023(4) Uani 1 1 d . . . H25A H 0.7629 0.2548 0.6056 0.034 Uiso 1 1 calc R . . H25B H 0.9899 0.2173 0.5982 0.034 Uiso 1 1 calc R . . H25C H 0.8720 0.3091 0.5202 0.034 Uiso 1 1 calc R . . C26 C 1.262(2) 0.3565(13) 0.5516(12) 0.023(4) Uani 1 1 d . . . H26A H 1.3896 0.3618 0.5682 0.034 Uiso 1 1 calc R . . H26B H 1.2413 0.3969 0.4913 0.034 Uiso 1 1 calc R . . H26C H 1.2550 0.2808 0.5634 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.0290(4) 0.0189(4) 0.0299(5) -0.0126(3) 0.0056(3) -0.0067(3) Pb2 0.0169(4) 0.0245(4) 0.0279(4) -0.0120(3) 0.0033(3) -0.0053(3) Pb3 0.0151(4) 0.0194(4) 0.0346(5) -0.0092(3) -0.0027(3) -0.0021(3) Pb4 0.0158(4) 0.0197(4) 0.0358(5) -0.0114(3) -0.0006(3) 0.0001(3) N1 0.024(8) 0.013(6) 0.030(9) -0.004(6) 0.002(7) -0.008(6) N2 0.024(8) 0.013(6) 0.030(9) -0.004(6) 0.002(7) -0.008(6) N3 0.016(8) 0.021(7) 0.031(9) -0.011(6) 0.002(6) -0.003(6) N4 0.016(7) 0.021(7) 0.031(9) -0.011(6) 0.002(6) -0.003(6) O1 0.018(6) 0.031(7) 0.039(8) -0.018(6) 0.017(6) -0.014(5) O2 0.017(6) 0.015(5) 0.029(7) -0.005(5) -0.006(5) -0.008(4) O3 0.014(6) 0.019(6) 0.031(7) -0.012(5) 0.002(5) -0.003(5) O4 0.024(6) 0.025(6) 0.018(7) -0.013(5) 0.001(5) -0.010(5) O5 0.018(6) 0.021(6) 0.042(8) -0.020(5) 0.010(6) -0.010(5) O6 0.024(7) 0.014(5) 0.029(7) -0.008(5) 0.000(5) -0.003(5) O7 0.024(7) 0.037(7) 0.076(12) -0.041(8) 0.001(7) -0.004(6) O8 0.026(7) 0.019(6) 0.047(9) -0.014(6) -0.006(6) -0.004(5) O9 0.021(7) 0.027(6) 0.044(9) -0.019(6) -0.004(6) 0.001(5) O10 0.016 0.018 0.056 -0.023 0.004 -0.002 C1 0.018(9) 0.016(8) 0.027(10) -0.003(7) -0.002(7) -0.004(7) C2 0.014(8) 0.016(8) 0.037(11) -0.015(7) 0.002(8) 0.002(6) C3 0.017(9) 0.019(8) 0.040(12) -0.016(8) -0.001(8) -0.004(7) C4 0.013(8) 0.011(7) 0.036(11) -0.010(7) -0.014(7) 0.001(6) C5 0.024(10) 0.013(8) 0.030(11) -0.004(7) 0.002(8) -0.008(7) C6 0.019(9) 0.019(8) 0.018(10) 0.007(7) -0.001(7) 0.000(7) C7 0.022(9) 0.023(8) 0.019(10) 0.003(7) 0.000(7) 0.001(7) C8 0.022(9) 0.023(9) 0.019(10) 0.003(7) 0.000(7) 0.001(7) C9 0.022(10) 0.023(9) 0.019(10) 0.003(7) 0.000(8) 0.001(7) C10 0.022(9) 0.023(8) 0.019(10) 0.003(7) 0.000(7) 0.001(7) C11 0.022(9) 0.023(8) 0.019(10) 0.003(7) 0.000(7) 0.001(7) C12 0.022(9) 0.023(9) 0.019(10) 0.003(7) 0.000(7) 0.001(7) C13 0.022(10) 0.023(9) 0.019(10) 0.003(7) 0.000(7) 0.001(7) C14 0.016(9) 0.021(8) 0.031(11) -0.011(8) 0.002(8) -0.003(7) C15 0.016(9) 0.021(8) 0.031(11) -0.011(8) 0.002(8) -0.003(7) C16 0.016(9) 0.021(8) 0.031(11) -0.011(8) 0.002(8) -0.003(7) C17 0.016(9) 0.021(8) 0.031(11) -0.011(8) 0.002(7) -0.003(7) C18 0.016(9) 0.021(8) 0.031(11) -0.011(8) 0.002(7) -0.003(7) C19 0.015(9) 0.022(8) 0.032(11) -0.011(8) 0.002(8) -0.003(7) C20 0.015(9) 0.022(8) 0.032(11) -0.011(8) 0.002(7) -0.003(7) C21 0.015(9) 0.022(8) 0.032(11) -0.011(7) 0.002(7) -0.003(7) C22 0.015(9) 0.022(9) 0.032(11) -0.011(8) 0.002(8) -0.003(7) C23 0.015(9) 0.022(8) 0.032(11) -0.011(8) 0.002(7) -0.003(7) C24 0.015(9) 0.022(8) 0.032(11) -0.011(8) 0.002(8) -0.003(7) C25 0.015(9) 0.022(8) 0.032(11) -0.011(8) 0.002(8) -0.003(7) C26 0.015(9) 0.022(8) 0.032(11) -0.011(8) 0.002(8) -0.003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 O10 2.265(13) . ? Pb1 O2 2.504(11) . ? Pb1 O8 2.573(13) 2_667 ? Pb1 N1 2.581(12) . ? Pb1 O6 2.699(11) 2_567 ? Pb2 O9 2.235(13) . ? Pb2 O4 2.448(11) 2_557 ? Pb2 O5 2.533(10) . ? Pb2 O3 2.682(11) 2_657 ? Pb2 N4 2.724(13) . ? Pb3 O9 2.246(12) . ? Pb3 O7 2.574(11) 2_667 ? Pb3 O1 2.631(11) . ? Pb3 O2 2.649(12) . ? Pb3 O1 2.670(12) 2_657 ? Pb3 O3 2.683(12) 2_657 ? Pb4 O10 2.280(12) . ? Pb4 O5 2.397(11) . ? Pb4 O4 2.523(10) 2_557 ? Pb4 O6 2.624(12) 2_567 ? N1 C5 1.33(2) . ? N1 C2 1.37(2) . ? N2 C5 1.39(2) . ? N2 C3 1.40(2) . ? N3 C16 1.30(2) . ? N3 C18 1.38(2) . ? N4 C18 1.31(2) . ? N4 C15 1.37(2) . ? O1 C1 1.28(2) . ? O1 Pb3 2.670(12) 2_657 ? O2 C1 1.267(18) . ? O3 C4 1.27(2) . ? O3 Pb2 2.682(11) 2_657 ? O3 Pb3 2.683(12) 2_657 ? O4 C4 1.268(18) . ? O4 Pb2 2.448(11) 2_557 ? O4 Pb4 2.523(10) 2_557 ? O5 C14 1.282(18) . ? O6 C14 1.27(2) . ? O6 Pb4 2.624(12) 2_567 ? O6 Pb1 2.699(11) 2_567 ? O7 C17 1.24(2) . ? O7 Pb3 2.574(11) 2_667 ? O8 C17 1.31(2) . ? O8 Pb1 2.573(13) 2_667 ? O9 H9A 0.9700 . ? O9 H9B 0.9700 . ? C1 C2 1.47(2) . ? C2 C3 1.40(2) . ? C3 C4 1.47(2) . ? C5 C6 1.46(2) . ? C6 C7 1.39(2) . ? C6 C11 1.40(2) . ? C7 C8 1.38(3) . ? C7 H7 0.9300 . ? C8 C9 1.40(2) . ? C8 C12 1.56(2) . ? C9 C10 1.38(2) . ? C9 C13 1.55(2) . ? C10 C11 1.45(2) . ? C10 H10B 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.48(2) . ? C15 C16 1.42(2) . ? C16 C17 1.51(2) . ? C18 C19 1.50(2) . ? C19 C24 1.38(2) . ? C19 C20 1.40(2) . ? C20 C21 1.39(2) . ? C20 H20 0.9300 . ? C21 C22 1.41(2) . ? C21 C25 1.52(2) . ? C22 C23 1.38(2) . ? C22 C26 1.52(2) . ? C23 C24 1.44(2) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10 Pb1 O2 75.5(4) . . ? O10 Pb1 O8 75.5(4) . 2_667 ? O2 Pb1 O8 68.9(3) . 2_667 ? O10 Pb1 N1 84.6(4) . . ? O2 Pb1 N1 65.1(4) . . ? O8 Pb1 N1 133.1(4) 2_667 . ? O10 Pb1 O6 74.6(4) . 2_567 ? O2 Pb1 O6 137.0(4) . 2_567 ? O8 Pb1 O6 74.2(4) 2_667 2_567 ? N1 Pb1 O6 140.0(4) . 2_567 ? O9 Pb2 O4 80.5(4) . 2_557 ? O9 Pb2 O5 70.6(4) . . ? O4 Pb2 O5 60.6(3) 2_557 . ? O9 Pb2 O3 66.6(4) . 2_657 ? O4 Pb2 O3 147.0(4) 2_557 2_657 ? O5 Pb2 O3 108.1(4) . 2_657 ? O9 Pb2 N4 104.5(4) . . ? O4 Pb2 N4 117.3(4) 2_557 . ? O5 Pb2 N4 62.9(4) . . ? O3 Pb2 N4 75.5(4) 2_657 . ? O9 Pb3 O7 85.7(4) . 2_667 ? O9 Pb3 O1 84.1(4) . . ? O7 Pb3 O1 124.7(4) 2_667 . ? O9 Pb3 O2 71.9(4) . . ? O7 Pb3 O2 76.3(4) 2_667 . ? O1 Pb3 O2 48.9(3) . . ? O9 Pb3 O1 69.5(4) . 2_657 ? O7 Pb3 O1 149.5(4) 2_667 2_657 ? O1 Pb3 O1 71.4(4) . 2_657 ? O2 Pb3 O1 110.4(3) . 2_657 ? O9 Pb3 O3 66.5(4) . 2_657 ? O7 Pb3 O3 92.1(4) 2_667 2_657 ? O1 Pb3 O3 131.3(4) . 2_657 ? O2 Pb3 O3 137.5(3) . 2_657 ? O1 Pb3 O3 62.4(3) 2_657 2_657 ? O10 Pb4 O5 88.5(4) . . ? O10 Pb4 O4 74.0(4) . 2_557 ? O5 Pb4 O4 61.4(3) . 2_557 ? O10 Pb4 O6 75.9(4) . 2_567 ? O5 Pb4 O6 100.4(4) . 2_567 ? O4 Pb4 O6 144.9(4) 2_557 2_567 ? C5 N1 C2 107.5(13) . . ? C5 N1 Pb1 136.9(11) . . ? C2 N1 Pb1 111.8(10) . . ? C5 N2 C3 103.9(13) . . ? C16 N3 C18 103.1(14) . . ? C18 N4 C15 105.0(13) . . ? C18 N4 Pb2 137.7(11) . . ? C15 N4 Pb2 112.4(10) . . ? C1 O1 Pb3 96.6(9) . . ? C1 O1 Pb3 131.8(11) . 2_657 ? Pb3 O1 Pb3 108.6(4) . 2_657 ? C1 O2 Pb1 117.1(10) . . ? C1 O2 Pb3 96.1(10) . . ? Pb1 O2 Pb3 135.1(4) . . ? C4 O3 Pb2 131.8(11) . 2_657 ? C4 O3 Pb3 123.8(10) . 2_657 ? Pb2 O3 Pb3 95.6(3) 2_657 2_657 ? C4 O4 Pb2 136.3(10) . 2_557 ? C4 O4 Pb4 102.7(10) . 2_557 ? Pb2 O4 Pb4 116.9(4) 2_557 2_557 ? C14 O5 Pb4 115.9(10) . . ? C14 O5 Pb2 125.6(10) . . ? Pb4 O5 Pb2 118.5(4) . . ? C14 O6 Pb4 137.9(11) . 2_567 ? C14 O6 Pb1 121.4(11) . 2_567 ? Pb4 O6 Pb1 93.1(3) 2_567 2_567 ? C17 O7 Pb3 121.3(11) . 2_667 ? C17 O8 Pb1 116.8(11) . 2_667 ? Pb2 O9 Pb3 125.0(6) . . ? Pb2 O9 H9A 106.1 . . ? Pb3 O9 H9A 106.1 . . ? Pb2 O9 H9B 106.1 . . ? Pb3 O9 H9B 106.1 . . ? H9A O9 H9B 106.3 . . ? Pb1 O10 Pb4 116.4(4) . . ? O2 C1 O1 118.1(15) . . ? O2 C1 C2 118.3(15) . . ? O1 C1 C2 123.6(14) . . ? N1 C2 C3 107.4(15) . . ? N1 C2 C1 119.0(13) . . ? C3 C2 C1 133.4(15) . . ? N2 C3 C2 108.6(14) . . ? N2 C3 C4 118.9(14) . . ? C2 C3 C4 132.4(16) . . ? O3 C4 O4 119.2(13) . . ? O3 C4 C3 121.6(13) . . ? O4 C4 C3 119.2(15) . . ? N1 C5 N2 112.5(15) . . ? N1 C5 C6 124.2(15) . . ? N2 C5 C6 123.3(15) . . ? C7 C6 C11 118.8(17) . . ? C7 C6 C5 119.8(16) . . ? C11 C6 C5 121.3(16) . . ? C8 C7 C6 122.8(17) . . ? C8 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? C7 C8 C9 118.5(16) . . ? C7 C8 C12 120.2(16) . . ? C9 C8 C12 121.1(16) . . ? C10 C9 C8 121.3(16) . . ? C10 C9 C13 117.3(15) . . ? C8 C9 C13 121.4(15) . . ? C9 C10 C11 119.0(16) . . ? C9 C10 H10B 120.5 . . ? C11 C10 H10B 120.5 . . ? C6 C11 C10 119.3(17) . . ? C6 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O6 C14 O5 120.3(15) . . ? O6 C14 C15 123.9(14) . . ? O5 C14 C15 115.7(14) . . ? N4 C15 C16 106.1(15) . . ? N4 C15 C14 121.2(14) . . ? C16 C15 C14 132.4(15) . . ? N3 C16 C15 110.9(15) . . ? N3 C16 C17 120.6(15) . . ? C15 C16 C17 127.3(16) . . ? O7 C17 O8 123.2(16) . . ? O7 C17 C16 123.4(16) . . ? O8 C17 C16 113.1(14) . . ? N4 C18 N3 114.8(15) . . ? N4 C18 C19 125.8(15) . . ? N3 C18 C19 119.4(14) . . ? C24 C19 C20 118.8(16) . . ? C24 C19 C18 120.7(15) . . ? C20 C19 C18 120.3(15) . . ? C21 C20 C19 121.6(16) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C20 C21 C22 118.6(15) . . ? C20 C21 C25 119.4(15) . . ? C22 C21 C25 122.0(15) . . ? C23 C22 C21 120.9(16) . . ? C23 C22 C26 120.7(15) . . ? C21 C22 C26 118.3(15) . . ? C22 C23 C24 118.7(15) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? C19 C24 C23 121.0(15) . . ? C19 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 5.299 _refine_diff_density_min -4.521 _refine_diff_density_rms 0.594 _database_code_depnum_ccdc_archive 'CCDC 937413' ####################################################################### # # 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_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C50 H36 N8 O8 Zn2), H2 O ' _chemical_formula_sum 'C100 H74 N16 O17 Zn4' _chemical_formula_weight 2033.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M '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 18.737(2) _cell_length_b 20.667(3) _cell_length_c 23.441(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9077(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3264 _cell_measurement_theta_min 2.544 _cell_measurement_theta_max 22.245 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4168 _exptl_absorpt_coefficient_mu 1.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7292 _exptl_absorpt_correction_T_max 0.8959 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44063 _diffrn_reflns_av_R_equivalents 0.1954 _diffrn_reflns_av_sigmaI/netI 0.1452 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7931 _reflns_number_gt 3638 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0103P)^2^+61.8948P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7931 _refine_ls_number_parameters 625 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1901 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.1990 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 Zn1 Zn 0.59834(6) 0.84542(5) 0.62269(4) 0.0353(3) Uani 1 1 d . . . Zn2 Zn 0.54219(6) 1.12665(5) 0.71339(5) 0.0371(3) Uani 1 1 d . . . N1 N 0.5710(4) 1.1649(4) 0.6318(3) 0.038(2) Uani 1 1 d . . . N2 N 0.6552(4) 1.1487(4) 0.7233(3) 0.0366(19) Uani 1 1 d . . . N3 N 0.5459(4) 1.0334(4) 0.6754(3) 0.0371(19) Uani 1 1 d . . . N4 N 0.5566(4) 0.9342(4) 0.6362(3) 0.0322(18) Uani 1 1 d . . . N5 N 0.6774(4) 0.8660(4) 0.5550(4) 0.047(2) Uani 1 1 d . . . N6 N 0.7007(4) 0.8362(4) 0.6648(4) 0.043(2) Uani 1 1 d . . . N7 N 0.5455(4) 0.7759(3) 0.6742(3) 0.0305(17) Uani 1 1 d . . . N8 N 0.4976(4) 0.6996(4) 0.7315(3) 0.0293(18) Uani 1 1 d . . . O1 O 0.4329(3) 1.1106(3) 0.6901(3) 0.0466(18) Uani 1 1 d . . . O2 O 0.3580(3) 1.0387(3) 0.6516(3) 0.056(2) Uani 1 1 d . . . O3 O 0.3639(4) 0.9241(4) 0.6167(4) 0.069(2) Uani 1 1 d . . . H3A H 0.3613 0.9605 0.6304 0.103 Uiso 1 1 calc R . . O4 O 0.4464(4) 0.8512(3) 0.6006(3) 0.056(2) Uani 1 1 d . . . O5 O 0.5690(3) 0.7764(3) 0.5603(2) 0.0391(16) Uani 1 1 d . . . O6 O 0.5109(4) 0.6832(3) 0.5483(3) 0.0522(19) Uani 1 1 d . . . O7 O 0.4574(4) 0.5987(3) 0.6100(3) 0.0538(19) Uani 1 1 d . . . H7A H 0.4725 0.6277 0.5893 0.081 Uiso 1 1 calc R . . O8 O 0.4472(3) 0.5791(3) 0.7028(3) 0.0430(17) Uani 1 1 d . . . C1 C 0.4178(5) 1.0565(5) 0.6682(4) 0.044(3) Uani 1 1 d . . . C2 C 0.4796(5) 1.0115(5) 0.6609(4) 0.034(2) Uani 1 1 d . . . C3 C 0.4855(5) 0.9509(4) 0.6378(4) 0.035(2) Uani 1 1 d . . . C4 C 0.4300(5) 0.9053(5) 0.6164(4) 0.044(3) Uani 1 1 d . . . C5 C 0.5903(5) 0.9850(5) 0.6593(4) 0.035(2) Uani 1 1 d . . . C6 C 0.6684(5) 0.9919(4) 0.6624(5) 0.041(3) Uani 1 1 d . . . C7 C 0.7076(6) 1.0040(5) 0.6133(6) 0.061(3) Uani 1 1 d . . . H7 H 0.6841 1.0081 0.5785 0.073 Uiso 1 1 calc R . . C8 C 0.7833(5) 1.0104(4) 0.6156(5) 0.042(3) Uani 1 1 d . . . C9 C 0.8143(5) 1.0027(5) 0.6676(5) 0.042(3) Uani 1 1 d . . . C10 C 0.7783(5) 0.9924(4) 0.7147(5) 0.042(2) Uani 1 1 d . . . H10 H 0.8025 0.9887 0.7492 0.051 Uiso 1 1 calc R . . C11 C 0.7041(5) 0.9869(5) 0.7137(6) 0.060(3) Uani 1 1 d . . . H11 H 0.6789 0.9798 0.7474 0.072 Uiso 1 1 calc R . . C12 C 0.8233(5) 1.0228(4) 0.5619(4) 0.042(3) Uani 1 1 d . . . H12C H 0.8486 0.9843 0.5509 0.063 Uiso 1 1 calc R . . H12A H 0.8567 1.0573 0.5679 0.063 Uiso 1 1 calc R . . H12B H 0.7905 1.0347 0.5323 0.063 Uiso 1 1 calc R . . C13 C 0.8963(5) 1.0083(4) 0.6752(4) 0.042(2) Uani 1 1 d . . . H13B H 0.9141 0.9702 0.6939 0.063 Uiso 1 1 calc R . . H13C H 0.9071 1.0457 0.6980 0.063 Uiso 1 1 calc R . . H13A H 0.9185 1.0126 0.6385 0.063 Uiso 1 1 calc R . . C14 C 0.5299(5) 1.1701(5) 0.5865(4) 0.047(3) Uani 1 1 d . . . H14 H 0.4807 1.1682 0.5914 0.056 Uiso 1 1 calc R . . C15 C 0.5564(6) 1.1784(5) 0.5315(5) 0.050(3) Uani 1 1 d . . . H15 H 0.5254 1.1807 0.5006 0.060 Uiso 1 1 calc R . . C16 C 0.6258(6) 1.1830(5) 0.5234(5) 0.050(3) Uani 1 1 d . . . H16 H 0.6435 1.1887 0.4867 0.060 Uiso 1 1 calc R . . C17 C 0.6730(6) 1.1792(5) 0.5695(5) 0.050(3) Uani 1 1 d . . . C18 C 0.6430(6) 1.1691(5) 0.6238(5) 0.050(3) Uani 1 1 d . . . C19 C 0.7495(6) 1.1850(5) 0.5659(5) 0.050(3) Uani 1 1 d . . . H19 H 0.7707 1.1922 0.5307 0.060 Uiso 1 1 calc R . . C20 C 0.7907(6) 1.1800(5) 0.6126(5) 0.050(3) Uani 1 1 d . . . H20 H 0.8398 1.1843 0.6087 0.060 Uiso 1 1 calc R . . C21 C 0.7622(6) 1.1686(5) 0.6669(5) 0.050(3) Uani 1 1 d . . . C22 C 0.6871(6) 1.1622(5) 0.6737(5) 0.050(3) Uani 1 1 d . . . C23 C 0.8019(6) 1.1624(5) 0.7178(5) 0.050(3) Uani 1 1 d . . . H23 H 0.8513 1.1664 0.7166 0.060 Uiso 1 1 calc R . . C24 C 0.7701(5) 1.1510(5) 0.7677(5) 0.050(3) Uani 1 1 d . . . H24 H 0.7970 1.1487 0.8009 0.060 Uiso 1 1 calc R . . C25 C 0.6971(5) 1.1426(5) 0.7696(4) 0.045(3) Uani 1 1 d . . . H25 H 0.6760 1.1322 0.8043 0.054 Uiso 1 1 calc R . . C26 C 0.7115(5) 0.8265(5) 0.7201(5) 0.048(3) Uani 1 1 d . . . H26 H 0.6721 0.8253 0.7443 0.058 Uiso 1 1 calc R . . C27 C 0.7795(6) 0.8180(5) 0.7438(5) 0.056(3) Uani 1 1 d . . . H27 H 0.7851 0.8111 0.7828 0.067 Uiso 1 1 calc R . . C28 C 0.8364(6) 0.8202(5) 0.7090(5) 0.056(3) Uani 1 1 d . . . H28 H 0.8818 0.8142 0.7241 0.067 Uiso 1 1 calc R . . C29 C 0.8290(6) 0.8313(5) 0.6505(5) 0.056(3) Uani 1 1 d . . . C30 C 0.7581(6) 0.8405(5) 0.6308(5) 0.056(3) Uani 1 1 d . . . C31 C 0.7462(5) 0.8542(5) 0.5725(4) 0.043(3) Uani 1 1 d . . . C32 C 0.8035(6) 0.8590(5) 0.5337(5) 0.056(3) Uani 1 1 d . . . C33 C 0.8747(6) 0.8480(5) 0.5557(5) 0.056(3) Uani 1 1 d . . . H33 H 0.9132 0.8492 0.5308 0.067 Uiso 1 1 calc R . . C34 C 0.8866(6) 0.8360(5) 0.6114(5) 0.056(3) Uani 1 1 d . . . H34 H 0.9331 0.8307 0.6244 0.067 Uiso 1 1 calc R . . C35 C 0.7885(6) 0.8744(5) 0.4778(5) 0.056(3) Uani 1 1 d . . . H35 H 0.8254 0.8769 0.4513 0.067 Uiso 1 1 calc R . . C36 C 0.7209(6) 0.8856(5) 0.4614(5) 0.056(3) Uani 1 1 d . . . H36 H 0.7109 0.8967 0.4238 0.067 Uiso 1 1 calc R . . C37 C 0.6657(6) 0.8805(6) 0.5012(5) 0.057(3) Uani 1 1 d . . . H37 H 0.6191 0.8877 0.4893 0.069 Uiso 1 1 calc R . . C38 C 0.5350(5) 0.7281(5) 0.5793(4) 0.037(2) Uani 1 1 d . . . C39 C 0.5223(5) 0.7261(5) 0.6410(4) 0.034(2) Uani 1 1 d . . . C40 C 0.4938(4) 0.6796(4) 0.6756(4) 0.032(2) Uani 1 1 d . . . C41 C 0.4645(5) 0.6157(5) 0.6636(4) 0.041(3) Uani 1 1 d . . . C42 C 0.5288(5) 0.7582(4) 0.7286(4) 0.035(2) Uani 1 1 d . . . C43 C 0.5449(5) 0.8006(4) 0.7778(4) 0.029(2) Uani 1 1 d . . . C44 C 0.5751(5) 0.7740(5) 0.8260(4) 0.038(2) Uani 1 1 d . . . H44 H 0.5806 0.7294 0.8283 0.045 Uiso 1 1 calc R . . C45 C 0.5978(5) 0.8130(5) 0.8719(4) 0.043(2) Uani 1 1 d . . . C46 C 0.5880(6) 0.8803(6) 0.8666(5) 0.058(3) Uani 1 1 d . . . C47 C 0.5577(5) 0.9060(5) 0.8187(4) 0.043(3) Uani 1 1 d . . . H47 H 0.5517 0.9506 0.8160 0.052 Uiso 1 1 calc R . . C48 C 0.5361(5) 0.8671(5) 0.7747(4) 0.037(2) Uani 1 1 d . . . H48 H 0.5153 0.8854 0.7425 0.045 Uiso 1 1 calc R . . C49 C 0.6113(6) 0.9252(5) 0.9163(4) 0.058(3) Uani 1 1 d . . . H49B H 0.5977 0.9689 0.9079 0.087 Uiso 1 1 calc R . . H49C H 0.6622 0.9229 0.9208 0.087 Uiso 1 1 calc R . . H49A H 0.5886 0.9115 0.9510 0.087 Uiso 1 1 calc R . . C50 C 0.6345(4) 0.7831(5) 0.9224(3) 0.047(3) Uani 1 1 d . . . H50B H 0.6098 0.7952 0.9567 0.070 Uiso 1 1 calc R . . H50A H 0.6829 0.7982 0.9242 0.070 Uiso 1 1 calc R . . H50C H 0.6341 0.7369 0.9186 0.070 Uiso 1 1 calc R . . O1W O 0.8295(4) 0.7572(6) 0.8786(4) 0.057(4) Uani 0.50 1 d PR . . H1A H 0.8639 0.7813 0.8906 0.085 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0335(6) 0.0351(6) 0.0373(6) -0.0021(5) 0.0010(5) 0.0019(5) Zn2 0.0308(6) 0.0371(6) 0.0434(7) -0.0043(6) 0.0028(5) 0.0002(5) N1 0.032(4) 0.043(5) 0.040(5) -0.001(4) -0.007(4) 0.005(4) N2 0.030(4) 0.040(5) 0.040(5) 0.002(4) -0.009(4) 0.003(4) N3 0.028(4) 0.035(5) 0.049(5) -0.001(4) 0.001(4) -0.002(4) N4 0.028(4) 0.033(5) 0.035(5) -0.003(4) 0.001(3) 0.004(4) N5 0.041(5) 0.048(6) 0.052(6) -0.009(5) 0.005(4) 0.003(4) N6 0.039(5) 0.037(5) 0.052(6) 0.001(4) 0.003(4) -0.004(4) N7 0.032(4) 0.028(4) 0.032(4) 0.000(4) -0.005(4) 0.001(3) N8 0.023(4) 0.035(5) 0.029(5) -0.002(4) 0.001(3) -0.001(3) O1 0.030(4) 0.037(4) 0.073(5) -0.020(4) 0.003(3) 0.004(3) O2 0.024(4) 0.059(5) 0.087(6) -0.021(4) -0.005(4) 0.005(3) O3 0.034(4) 0.062(6) 0.109(7) -0.035(5) -0.017(4) 0.008(4) O4 0.056(5) 0.039(4) 0.075(5) -0.022(4) -0.023(4) 0.008(4) O5 0.046(4) 0.043(4) 0.029(4) -0.005(3) 0.000(3) 0.001(3) O6 0.062(5) 0.058(5) 0.036(4) -0.012(4) -0.008(4) -0.010(4) O7 0.066(5) 0.046(5) 0.050(5) -0.010(4) 0.000(4) -0.014(4) O8 0.047(4) 0.040(4) 0.043(4) 0.002(3) 0.012(3) 0.000(3) C1 0.023(6) 0.056(8) 0.053(7) -0.005(6) 0.010(5) 0.005(5) C2 0.031(6) 0.039(6) 0.033(6) -0.001(5) 0.005(4) 0.002(4) C3 0.038(6) 0.027(6) 0.042(6) -0.003(5) -0.001(4) 0.000(4) C4 0.041(6) 0.049(7) 0.041(6) -0.004(5) -0.018(5) 0.003(5) C5 0.030(5) 0.038(6) 0.038(6) -0.001(5) 0.000(5) -0.001(5) C6 0.031(6) 0.025(6) 0.069(8) -0.001(5) -0.004(6) 0.001(4) C7 0.046(7) 0.028(6) 0.109(10) -0.009(6) 0.007(7) 0.002(5) C8 0.033(6) 0.032(6) 0.062(7) -0.002(5) 0.003(5) 0.001(4) C9 0.033(6) 0.032(6) 0.062(7) -0.002(5) 0.003(6) 0.001(5) C10 0.033(6) 0.032(6) 0.062(7) -0.002(5) 0.003(5) 0.001(4) C11 0.041(7) 0.046(7) 0.092(9) -0.015(7) -0.014(7) 0.005(5) C12 0.033(6) 0.032(6) 0.062(7) -0.002(5) 0.003(5) 0.001(4) C13 0.033(6) 0.032(6) 0.062(7) -0.002(5) 0.003(5) 0.001(4) C14 0.043(6) 0.058(8) 0.040(6) 0.001(5) -0.002(5) 0.006(5) C15 0.048(7) 0.043(7) 0.058(7) -0.003(5) 0.001(6) -0.002(5) C16 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C17 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C18 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C19 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C20 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C21 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C22 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C23 0.048(6) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C24 0.048(7) 0.043(7) 0.058(7) -0.003(6) 0.001(6) -0.002(5) C25 0.036(6) 0.048(7) 0.052(7) 0.013(5) -0.002(5) -0.010(5) C26 0.040(6) 0.045(7) 0.059(7) 0.001(6) 0.015(6) 0.002(5) C27 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C28 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(5) C29 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C30 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C31 0.032(6) 0.042(7) 0.054(7) -0.014(5) 0.012(5) -0.005(5) C32 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C33 0.047(7) 0.056(8) 0.066(8) -0.004(7) 0.006(6) -0.007(6) C34 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C35 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C36 0.047(7) 0.056(8) 0.066(8) -0.004(6) 0.006(6) -0.007(6) C37 0.043(7) 0.078(9) 0.051(7) -0.011(6) -0.006(6) -0.012(6) C38 0.037(6) 0.035(6) 0.038(6) -0.004(5) -0.005(5) 0.000(5) C39 0.031(5) 0.035(6) 0.036(6) 0.000(5) -0.005(4) 0.005(4) C40 0.025(5) 0.026(5) 0.046(6) -0.002(5) -0.006(4) 0.002(4) C41 0.028(5) 0.045(7) 0.050(7) -0.019(6) 0.013(5) 0.001(5) C42 0.028(5) 0.034(6) 0.045(6) 0.006(5) 0.002(4) 0.000(4) C43 0.028(5) 0.029(5) 0.031(5) -0.001(4) 0.002(4) -0.007(4) C44 0.034(6) 0.036(6) 0.043(6) 0.002(5) 0.001(5) -0.004(4) C45 0.050(6) 0.050(7) 0.029(5) 0.003(5) -0.004(5) -0.002(5) C46 0.064(8) 0.057(8) 0.053(7) -0.016(6) 0.001(6) -0.015(6) C47 0.052(7) 0.039(6) 0.039(6) -0.004(5) 0.003(5) 0.005(5) C48 0.029(5) 0.047(6) 0.035(5) -0.004(5) 0.004(4) 0.005(5) C49 0.063(8) 0.058(8) 0.054(7) -0.011(6) 0.001(6) -0.018(6) C50 0.053(7) 0.054(7) 0.034(6) 0.002(5) -0.003(5) 0.002(5) O1W 0.047(8) 0.057(10) 0.066(10) -0.004(8) 0.005(8) -0.007(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N4 2.020(7) . ? Zn1 O5 2.115(6) . ? Zn1 N7 2.122(7) . ? Zn1 N6 2.165(8) . ? Zn1 N5 2.212(8) . ? Zn2 N8 2.121(7) 4_656 ? Zn2 N3 2.124(8) . ? Zn2 N1 2.138(8) . ? Zn2 O1 2.146(6) . ? Zn2 N2 2.179(7) . ? Zn2 O8 2.206(6) 4_656 ? N1 C14 1.317(11) . ? N1 C18 1.365(12) . ? N2 C22 1.338(12) . ? N2 C25 1.344(11) . ? N3 C5 1.355(11) . ? N3 C2 1.366(11) . ? N4 C5 1.341(11) . ? N4 C3 1.376(11) . ? N5 C37 1.314(12) . ? N5 C31 1.374(12) . ? N6 C26 1.329(12) . ? N6 C30 1.341(12) . ? N7 C39 1.362(10) . ? N7 C42 1.363(11) . ? N8 C42 1.347(11) . ? N8 C40 1.375(10) . ? N8 Zn2 2.121(7) 4_646 ? O1 C1 1.262(11) . ? O2 C1 1.243(11) . ? O3 C4 1.297(11) . ? O3 H3A 0.8200 . ? O4 C4 1.219(11) . ? O5 C38 1.265(10) . ? O6 C38 1.262(10) . ? O7 C41 1.311(11) . ? O7 H7A 0.8200 . ? O8 C41 1.234(11) . ? O8 Zn2 2.206(6) 4_646 ? C1 C2 1.494(12) . ? C2 C3 1.369(12) . ? C3 C4 1.491(13) . ? C5 C6 1.471(12) . ? C6 C11 1.381(14) . ? C6 C7 1.388(14) . ? C7 C8 1.427(14) . ? C7 H7 0.9300 . ? C8 C9 1.359(13) . ? C8 C12 1.486(13) . ? C9 C10 1.311(13) . ? C9 C13 1.552(12) . ? C10 C11 1.396(13) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13 H13A 0.9600 . ? C14 C15 1.392(13) . ? C14 H14 0.9300 . ? C15 C16 1.316(13) . ? C15 H15 0.9300 . ? C16 C17 1.398(14) . ? C16 H16 0.9300 . ? C17 C18 1.408(14) . ? C17 C19 1.440(14) . ? C18 C22 1.439(14) . ? C19 C20 1.343(13) . ? C19 H19 0.9300 . ? C20 C21 1.399(13) . ? C20 H20 0.9300 . ? C21 C23 1.413(13) . ? C21 C22 1.422(13) . ? C23 C24 1.332(13) . ? C23 H23 0.9300 . ? C24 C25 1.380(13) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.400(14) . ? C26 H26 0.9300 . ? C27 C28 1.345(13) . ? C27 H27 0.9300 . ? C28 C29 1.396(14) . ? C28 H28 0.9300 . ? C29 C34 1.419(14) . ? C29 C30 1.420(14) . ? C30 C31 1.414(14) . ? C31 C32 1.410(13) . ? C32 C35 1.376(14) . ? C32 C33 1.448(14) . ? C33 C34 1.347(14) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 C36 1.345(14) . ? C35 H35 0.9300 . ? C36 C37 1.397(14) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 C39 1.467(13) . ? C39 C40 1.365(12) . ? C40 C41 1.459(12) . ? C42 C43 1.479(12) . ? C43 C44 1.377(12) . ? C43 C48 1.386(12) . ? C44 C45 1.410(12) . ? C44 H44 0.9300 . ? C45 C46 1.407(14) . ? C45 C50 1.503(11) . ? C46 C47 1.366(13) . ? C46 C49 1.552(13) . ? C47 C48 1.370(12) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C49 H49A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50A 0.9600 . ? C50 H50C 0.9600 . ? O1W H1A 0.8631 . ? 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 Zn1 O5 128.3(3) . . ? N4 Zn1 N7 110.2(3) . . ? O5 Zn1 N7 79.4(3) . . ? N4 Zn1 N6 110.6(3) . . ? O5 Zn1 N6 119.0(3) . . ? N7 Zn1 N6 95.4(3) . . ? N4 Zn1 N5 101.4(3) . . ? O5 Zn1 N5 78.9(3) . . ? N7 Zn1 N5 148.3(3) . . ? N6 Zn1 N5 75.5(3) . . ? N8 Zn2 N3 155.8(3) 4_656 . ? N8 Zn2 N1 111.8(3) 4_656 . ? N3 Zn2 N1 87.2(3) . . ? N8 Zn2 O1 86.0(3) 4_656 . ? N3 Zn2 O1 77.6(3) . . ? N1 Zn2 O1 94.0(3) . . ? N8 Zn2 N2 97.3(3) 4_656 . ? N3 Zn2 N2 101.7(3) . . ? N1 Zn2 N2 76.9(3) . . ? O1 Zn2 N2 170.9(3) . . ? N8 Zn2 O8 78.8(3) 4_656 4_656 ? N3 Zn2 O8 88.1(3) . 4_656 ? N1 Zn2 O8 159.8(3) . 4_656 ? O1 Zn2 O8 104.1(3) . 4_656 ? N2 Zn2 O8 84.9(3) . 4_656 ? C14 N1 C18 117.4(9) . . ? C14 N1 Zn2 127.3(7) . . ? C18 N1 Zn2 113.3(6) . . ? C22 N2 C25 117.4(8) . . ? C22 N2 Zn2 112.6(6) . . ? C25 N2 Zn2 129.4(6) . . ? C5 N3 C2 104.2(7) . . ? C5 N3 Zn2 143.8(6) . . ? C2 N3 Zn2 112.0(6) . . ? C5 N4 C3 104.4(7) . . ? C5 N4 Zn1 126.3(6) . . ? C3 N4 Zn1 127.4(6) . . ? C37 N5 C31 118.8(9) . . ? C37 N5 Zn1 128.3(7) . . ? C31 N5 Zn1 112.4(7) . . ? C26 N6 C30 117.9(9) . . ? C26 N6 Zn1 126.4(7) . . ? C30 N6 Zn1 115.7(7) . . ? C39 N7 C42 104.9(7) . . ? C39 N7 Zn1 109.6(6) . . ? C42 N7 Zn1 145.2(6) . . ? C42 N8 C40 104.2(7) . . ? C42 N8 Zn2 145.3(6) . 4_646 ? C40 N8 Zn2 110.4(6) . 4_646 ? C1 O1 Zn2 117.0(6) . . ? C4 O3 H3A 109.5 . . ? C38 O5 Zn1 114.8(6) . . ? C41 O7 H7A 109.5 . . ? C41 O8 Zn2 111.6(6) . 4_646 ? O2 C1 O1 126.2(9) . . ? O2 C1 C2 118.6(9) . . ? O1 C1 C2 115.1(8) . . ? N3 C2 C3 109.1(8) . . ? N3 C2 C1 118.1(8) . . ? C3 C2 C1 132.6(9) . . ? C2 C3 N4 108.6(8) . . ? C2 C3 C4 130.9(9) . . ? N4 C3 C4 120.5(8) . . ? O4 C4 O3 121.2(9) . . ? O4 C4 C3 120.4(9) . . ? O3 C4 C3 118.4(9) . . ? N4 C5 N3 113.7(8) . . ? N4 C5 C6 124.4(8) . . ? N3 C5 C6 121.7(8) . . ? C11 C6 C7 118.8(10) . . ? C11 C6 C5 121.1(10) . . ? C7 C6 C5 120.1(10) . . ? C6 C7 C8 120.7(12) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 116.6(10) . . ? C9 C8 C12 124.4(9) . . ? C7 C8 C12 119.0(10) . . ? C10 C9 C8 123.7(9) . . ? C10 C9 C13 115.1(9) . . ? C8 C9 C13 121.1(9) . . ? C9 C10 C11 120.8(11) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C6 C11 C10 119.4(11) . . ? C6 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C8 C12 H12C 109.5 . . ? C8 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C13 H13A 109.5 . . ? H13B C13 H13A 109.5 . . ? H13C C13 H13A 109.5 . . ? N1 C14 C15 123.4(10) . . ? N1 C14 H14 118.3 . . ? C15 C14 H14 118.3 . . ? C16 C15 C14 119.6(11) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.6(11) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 117.0(10) . . ? C16 C17 C19 125.5(10) . . ? C18 C17 C19 117.5(10) . . ? N1 C18 C17 121.9(10) . . ? N1 C18 C22 116.8(9) . . ? C17 C18 C22 121.3(10) . . ? C20 C19 C17 121.2(10) . . ? C20 C19 H19 119.4 . . ? C17 C19 H19 119.4 . . ? C19 C20 C21 122.3(10) . . ? C19 C20 H20 118.8 . . ? C21 C20 H20 118.8 . . ? C20 C21 C23 125.7(10) . . ? C20 C21 C22 119.7(10) . . ? C23 C21 C22 114.6(10) . . ? N2 C22 C21 124.0(10) . . ? N2 C22 C18 118.1(9) . . ? C21 C22 C18 117.9(10) . . ? C24 C23 C21 121.5(10) . . ? C24 C23 H23 119.2 . . ? C21 C23 H23 119.2 . . ? C23 C24 C25 119.6(10) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? N2 C25 C24 122.7(9) . . ? N2 C25 H25 118.6 . . ? C24 C25 H25 118.6 . . ? N6 C26 C27 123.1(10) . . ? N6 C26 H26 118.5 . . ? C27 C26 H26 118.5 . . ? C28 C27 C26 118.4(11) . . ? C28 C27 H27 120.8 . . ? C26 C27 H27 120.8 . . ? C27 C28 C29 121.5(11) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C28 C29 C34 124.7(11) . . ? C28 C29 C30 115.8(10) . . ? C34 C29 C30 119.5(11) . . ? N6 C30 C31 117.5(10) . . ? N6 C30 C29 123.2(10) . . ? C31 C30 C29 119.3(10) . . ? N5 C31 C32 120.7(10) . . ? N5 C31 C30 118.1(9) . . ? C32 C31 C30 121.2(10) . . ? C35 C32 C31 118.3(10) . . ? C35 C32 C33 124.3(10) . . ? C31 C32 C33 117.4(10) . . ? C34 C33 C32 121.8(10) . . ? C34 C33 H33 119.1 . . ? C32 C33 H33 119.1 . . ? C33 C34 C29 120.9(11) . . ? C33 C34 H34 119.6 . . ? C29 C34 H34 119.6 . . ? C36 C35 C32 120.3(11) . . ? C36 C35 H35 119.9 . . ? C32 C35 H35 119.9 . . ? C35 C36 C37 119.5(11) . . ? C35 C36 H36 120.2 . . ? C37 C36 H36 120.2 . . ? N5 C37 C36 122.4(10) . . ? N5 C37 H37 118.8 . . ? C36 C37 H37 118.8 . . ? O6 C38 O5 124.0(9) . . ? O6 C38 C39 119.2(9) . . ? O5 C38 C39 116.8(8) . . ? N7 C39 C40 108.5(8) . . ? N7 C39 C38 119.3(8) . . ? C40 C39 C38 132.0(9) . . ? C39 C40 N8 109.6(8) . . ? C39 C40 C41 132.0(9) . . ? N8 C40 C41 118.4(8) . . ? O8 C41 O7 121.5(9) . . ? O8 C41 C40 120.6(9) . . ? O7 C41 C40 117.8(9) . . ? N8 C42 N7 112.8(8) . . ? N8 C42 C43 125.7(8) . . ? N7 C42 C43 121.5(8) . . ? C44 C43 C48 119.2(8) . . ? C44 C43 C42 119.1(8) . . ? C48 C43 C42 121.5(8) . . ? C43 C44 C45 121.4(9) . . ? C43 C44 H44 119.3 . . ? C45 C44 H44 119.3 . . ? C46 C45 C44 117.3(9) . . ? C46 C45 C50 122.3(9) . . ? C44 C45 C50 120.3(9) . . ? C47 C46 C45 120.7(10) . . ? C47 C46 C49 120.1(10) . . ? C45 C46 C49 119.3(10) . . ? C46 C47 C48 120.9(10) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C47 C48 C43 120.5(9) . . ? C47 C48 H48 119.7 . . ? C43 C48 H48 119.7 . . ? C46 C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C46 C49 H49A 109.5 . . ? H49B C49 H49A 109.5 . . ? H49C C49 H49A 109.5 . . ? C45 C50 H50B 109.5 . . ? C45 C50 H50A 109.5 . . ? H50B C50 H50A 109.5 . . ? C45 C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.82 1.69 2.509(10) 173.9 . O7 H7A O6 0.82 1.66 2.479(10) 174.5 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.788 _refine_diff_density_min -2.255 _refine_diff_density_rms 0.127 _database_code_depnum_ccdc_archive 'CCDC 937414' ####################################################################### # # 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_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C65 H55 Mn3 N10 O16' _chemical_formula_weight 1397.01 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' Mn Mn 0.3368 0.7283 '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 ' 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 33.287(4) _cell_length_b 7.5503(8) _cell_length_c 25.231(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.425(2) _cell_angle_gamma 90.00 _cell_volume 6312.8(12) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3283 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 25.20 _exptl_crystal_description prsim _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2872 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8245 _exptl_absorpt_correction_T_max 0.9361 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 area-detector' _diffrn_measurement_method '\f and \w' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15090 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5524 _reflns_number_gt 3609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+60.6155P] 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 5524 _refine_ls_number_parameters 501 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0738 _refine_ls_wR_factor_ref 0.1885 _refine_ls_wR_factor_gt 0.1664 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.18345(3) 0.02928(12) 0.27822(3) 0.0401(3) Uani 1 1 d . . . Mn2 Mn 0.2500 0.7500 0.5000 0.0438(4) Uani 1 2 d S . . N1 N 0.18911(15) 0.1866(6) 0.20032(16) 0.0411(12) Uani 1 1 d . . . N2 N 0.19584(15) 0.2892(6) 0.12050(16) 0.0412(12) Uani 1 1 d . . . H2 H 0.1900 0.3178 0.0877 0.049 Uiso 1 1 calc R . . N3 N 0.22867(15) 0.3341(6) 0.38009(17) 0.0420(12) Uani 1 1 d . . . H3 H 0.2342 0.2639 0.3549 0.050 Uiso 1 1 calc R . . N4 N 0.23711(16) 0.5070(6) 0.45032(16) 0.0434(12) Uani 1 1 d . . . O1 O 0.24198(12) 0.1546(5) 0.28674(13) 0.0450(10) Uani 1 1 d . . . O2 O 0.29066(13) 0.2968(6) 0.25137(15) 0.0490(11) Uani 1 1 d . . . O3 O 0.29898(13) 0.4270(6) 0.14398(14) 0.0482(11) Uani 1 1 d . . . O4 O 0.25815(14) 0.4023(6) 0.07021(13) 0.0510(11) Uani 1 1 d . . . O5 O 0.15636(14) 0.2586(6) 0.31275(16) 0.0564(12) Uani 1 1 d . . . O6 O 0.12164(14) 0.4200(7) 0.36422(18) 0.0714(15) Uani 1 1 d . . . H6A H 0.1257 0.4804 0.3912 0.107 Uiso 1 1 calc R . . O7 O 0.13121(15) 0.6074(7) 0.44387(18) 0.0676(14) Uani 1 1 d . . . O8 O 0.18295(14) 0.7061(6) 0.49808(15) 0.0533(12) Uani 1 1 d . . . C1 C 0.2563(2) 0.2318(7) 0.2481(2) 0.0389(14) Uani 1 1 d . . . C2 C 0.22820(19) 0.2414(7) 0.19819(19) 0.0380(14) Uani 1 1 d . . . C3 C 0.23296(19) 0.3063(7) 0.14765(19) 0.0396(14) Uani 1 1 d . . . C4 C 0.16950(19) 0.2205(8) 0.1527(2) 0.0417(14) Uani 1 1 d . . . C5 C 0.1264(2) 0.1989(9) 0.1375(2) 0.0482(16) Uani 1 1 d . . . C6 C 0.1090(2) 0.2168(10) 0.0855(2) 0.062(2) Uani 1 1 d . A . H6 H 0.1259 0.2384 0.0588 0.074 Uiso 1 1 calc R . . C7 C 0.0686(2) 0.2043(11) 0.0717(3) 0.069(2) Uani 1 1 d . . . H7 H 0.0583 0.2197 0.0364 0.103 Uiso 0.251(13) 1 calc PR A 2 C8 C 0.0429(2) 0.1683(13) 0.1106(3) 0.082(3) Uani 1 1 d . A . C9 C 0.0595(3) 0.1479(14) 0.1628(3) 0.086(3) Uani 1 1 d . . . H9 H 0.0427 0.1202 0.1891 0.129 Uiso 0.749(13) 1 calc PR A 1 C10 C 0.1002(2) 0.1677(11) 0.1766(3) 0.072(2) Uani 1 1 d . A . H10 H 0.1103 0.1602 0.2121 0.086 Uiso 1 1 calc R . . C11 C 0.26658(19) 0.3833(8) 0.1194(2) 0.0389(14) Uani 1 1 d . . . C12 C 0.0488(3) 0.2382(15) 0.0158(4) 0.072(3) Uani 0.749(13) 1 d P A 1 H12A H 0.0338 0.1352 0.0034 0.108 Uiso 0.749(13) 1 calc PR A 1 H12B H 0.0692 0.2630 -0.0077 0.108 Uiso 0.749(13) 1 calc PR A 1 H12C H 0.0309 0.3376 0.0164 0.108 Uiso 0.749(13) 1 calc PR A 1 C12' C 0.0367(10) 0.105(6) 0.2021(13) 0.091(13) Uani 0.251(13) 1 d P A 2 H12D H 0.0515 0.1284 0.2359 0.137 Uiso 0.251(13) 1 calc PR A 2 H12E H 0.0301 -0.0191 0.1998 0.137 Uiso 0.251(13) 1 calc PR A 2 H12F H 0.0124 0.1734 0.1988 0.137 Uiso 0.251(13) 1 calc PR A 2 C13 C -0.0024(2) 0.1476(13) 0.0975(3) 0.087(3) Uani 1 1 d . . . H13A H -0.0138 0.2588 0.0852 0.130 Uiso 1 1 calc R A . H13B H -0.0144 0.1111 0.1288 0.130 Uiso 1 1 calc R . . H13C H -0.0075 0.0599 0.0702 0.130 Uiso 1 1 calc R . . C14 C 0.1547(2) 0.3557(9) 0.3522(2) 0.0502(16) Uani 1 1 d . . . C15 C 0.19122(19) 0.3999(8) 0.3867(2) 0.0426(15) Uani 1 1 d . . . C16 C 0.19702(19) 0.5067(8) 0.4309(2) 0.0423(15) Uani 1 1 d . . . C17 C 0.25581(19) 0.3962(8) 0.4193(2) 0.0417(15) Uani 1 1 d . . . C18 C 0.29782(19) 0.3463(8) 0.4275(2) 0.0440(15) Uani 1 1 d . . . C19 C 0.3193(2) 0.3787(9) 0.4771(2) 0.0515(17) Uani 1 1 d . . . H19 H 0.3060 0.4292 0.5041 0.062 Uiso 1 1 calc R . . C20 C 0.3596(2) 0.3376(9) 0.4868(3) 0.0567(18) Uani 1 1 d . . . C21 C 0.3797(2) 0.2535(10) 0.4482(3) 0.065(2) Uani 1 1 d . . . C22 C 0.3580(2) 0.2171(10) 0.3990(3) 0.067(2) Uani 1 1 d . . . H22 H 0.3711 0.1610 0.3727 0.081 Uiso 1 1 calc R . . C23 C 0.3180(2) 0.2619(9) 0.3884(2) 0.0555(18) Uani 1 1 d . . . H23 H 0.3044 0.2361 0.3554 0.067 Uiso 1 1 calc R . . C24 C 0.1687(2) 0.6154(9) 0.4595(2) 0.0487(16) Uani 1 1 d . . . C25 C 0.3811(3) 0.3905(13) 0.5396(3) 0.089(3) Uani 1 1 d . . . H25A H 0.3947 0.2893 0.5559 0.134 Uiso 1 1 calc R . . H25B H 0.3618 0.4346 0.5624 0.134 Uiso 1 1 calc R . . H25C H 0.4005 0.4812 0.5343 0.134 Uiso 1 1 calc R . . C26 C 0.4237(2) 0.2059(13) 0.4560(4) 0.098(3) Uani 1 1 d . . . H26A H 0.4394 0.3109 0.4640 0.147 Uiso 1 1 calc R . . H26B H 0.4317 0.1528 0.4241 0.147 Uiso 1 1 calc R . . H26C H 0.4282 0.1236 0.4850 0.147 Uiso 1 1 calc R . . N5 N 0.12545(18) -0.1185(9) 0.2777(2) 0.0610(15) Uani 1 1 d . . . C27 C 0.1194(18) -0.262(8) 0.2445(14) 0.061(7) Uani 0.55(2) 1 d P B 3 H27 H 0.1380 -0.2841 0.2201 0.073 Uiso 0.55(2) 1 calc PR B 3 C28 C 0.0870(7) -0.375(3) 0.2457(8) 0.061(5) Uani 0.55(2) 1 d P B 3 H28 H 0.0863 -0.4808 0.2267 0.073 Uiso 0.55(2) 1 calc PR B 3 C29 C 0.0551(5) -0.331(2) 0.2757(8) 0.061(5) Uani 0.55(2) 1 d P B 3 C30 C 0.0576(5) -0.175(2) 0.2975(7) 0.061(4) Uani 0.55(2) 1 d P B 3 H30 H 0.0355 -0.1319 0.3136 0.073 Uiso 0.55(2) 1 calc PR B 3 C31 C 0.0920(7) -0.068(3) 0.2980(9) 0.061(5) Uani 0.55(2) 1 d P B 3 H31 H 0.0914 0.0445 0.3132 0.073 Uiso 0.55(2) 1 calc PR B 3 C32 C 0.0196(6) -0.460(2) 0.2816(7) 0.061(5) Uani 0.55(2) 1 d P . 3 H32B H 0.0277 -0.5215 0.3147 0.091 Uiso 0.55(2) 1 calc PR B 3 H32A H -0.0022 -0.3825 0.2895 0.091 Uiso 0.55(2) 1 calc PR B 3 C33 C 0.0000 -0.592(3) 0.2500 0.061(6) Uani 0.55(2) 2 d SP . 3 H33A H -0.0181 -0.6646 0.2688 0.073 Uiso 0.277(11) 1 calc PR B 3 H33B H 0.0181 -0.6646 0.2312 0.073 Uiso 0.277(11) 1 calc PR B 3 C27' C 0.120(2) -0.285(10) 0.2616(16) 0.061(10) Uani 0.45(2) 1 d P B 4 H27' H 0.1399 -0.3370 0.2425 0.073 Uiso 0.45(2) 1 calc PR B 4 C28' C 0.0872(9) -0.384(4) 0.2720(10) 0.061(6) Uani 0.45(2) 1 d P B 4 H28' H 0.0811 -0.4865 0.2524 0.073 Uiso 0.45(2) 1 calc PR B 4 C29' C 0.0625(6) -0.334(3) 0.3113(10) 0.061(6) Uani 0.45(2) 1 d P B 4 C30' C 0.0718(6) -0.184(3) 0.3310(10) 0.061(6) Uani 0.45(2) 1 d P B 4 H30' H 0.0556 -0.1379 0.3557 0.073 Uiso 0.45(2) 1 calc PR B 4 C31' C 0.1040(9) -0.084(4) 0.3184(11) 0.061(6) Uani 0.45(2) 1 d P B 4 H31' H 0.1113 0.0132 0.3396 0.073 Uiso 0.45(2) 1 calc PR B 4 C32' C 0.0211(6) -0.414(3) 0.3090(9) 0.061(6) Uani 0.45(2) 1 d P B 4 H32C H 0.0041 -0.3388 0.3286 0.073 Uiso 0.45(2) 1 calc PR B 4 H32D H 0.0230 -0.5285 0.3266 0.073 Uiso 0.45(2) 1 calc PR B 4 C33' C 0.0000 -0.440(4) 0.2500 0.061(8) Uani 0.45(2) 2 d SP . 4 H33C H -0.0206 -0.5199 0.2607 0.073 Uiso 0.223(11) 1 calc PR B 4 H33D H 0.0206 -0.5199 0.2393 0.073 Uiso 0.223(11) 1 calc PR B 4 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 0.0561(6) 0.0402(5) 0.0233(4) -0.0021(4) 0.0005(4) -0.0008(5) Mn2 0.0733(10) 0.0403(7) 0.0166(5) -0.0035(5) -0.0013(5) 0.0021(7) N1 0.063(3) 0.037(3) 0.023(2) 0.001(2) 0.001(2) -0.002(3) N2 0.062(3) 0.041(3) 0.020(2) 0.000(2) -0.002(2) -0.003(2) N3 0.059(3) 0.038(3) 0.028(2) -0.007(2) -0.002(2) 0.007(2) N4 0.066(4) 0.040(3) 0.023(2) -0.005(2) -0.002(2) 0.003(3) O1 0.064(3) 0.050(3) 0.0208(18) 0.0021(17) -0.0006(17) -0.006(2) O2 0.058(3) 0.051(3) 0.036(2) 0.0119(19) -0.0052(19) -0.009(2) O3 0.060(3) 0.061(3) 0.0233(19) -0.0024(18) 0.0049(19) -0.003(2) O4 0.087(3) 0.047(2) 0.0179(18) 0.0008(17) 0.0019(19) -0.013(2) O5 0.072(3) 0.054(3) 0.040(2) -0.020(2) -0.009(2) 0.010(2) O6 0.062(3) 0.093(4) 0.056(3) -0.034(3) -0.013(2) 0.015(3) O7 0.064(3) 0.081(4) 0.057(3) -0.027(3) 0.001(2) 0.015(3) O8 0.079(3) 0.053(3) 0.028(2) -0.0143(19) 0.003(2) 0.006(2) C1 0.064(4) 0.031(3) 0.021(3) 0.001(2) 0.004(3) 0.003(3) C2 0.060(4) 0.032(3) 0.021(3) 0.000(2) 0.001(2) -0.001(3) C3 0.064(4) 0.033(3) 0.021(3) -0.004(2) -0.001(3) 0.000(3) C4 0.061(4) 0.033(3) 0.030(3) -0.002(2) 0.000(3) -0.002(3) C5 0.058(4) 0.046(4) 0.040(3) 0.003(3) 0.001(3) -0.002(3) C6 0.078(5) 0.070(5) 0.035(3) 0.001(3) -0.006(3) -0.018(4) C7 0.070(5) 0.080(6) 0.051(4) 0.001(4) -0.015(4) -0.019(4) C8 0.066(5) 0.103(7) 0.073(5) 0.005(5) -0.012(4) -0.027(5) C9 0.070(6) 0.120(8) 0.069(5) 0.019(5) 0.012(4) -0.005(5) C10 0.067(5) 0.093(6) 0.053(4) 0.018(4) -0.005(4) -0.002(5) C11 0.061(4) 0.035(3) 0.021(3) -0.002(2) 0.007(3) 0.002(3) C12 0.076(7) 0.083(8) 0.052(6) 0.005(5) -0.015(5) -0.016(6) C12' 0.08(2) 0.13(3) 0.07(2) 0.02(2) 0.005(18) 0.00(2) C13 0.074(6) 0.106(7) 0.076(5) 0.006(5) -0.010(4) -0.030(5) C14 0.062(4) 0.049(4) 0.038(3) -0.007(3) -0.005(3) 0.005(3) C15 0.059(4) 0.038(3) 0.029(3) -0.003(2) -0.003(3) 0.004(3) C16 0.058(4) 0.043(4) 0.025(3) -0.005(2) -0.001(3) 0.008(3) C17 0.068(4) 0.034(3) 0.021(3) 0.000(2) -0.002(3) 0.002(3) C18 0.058(4) 0.039(3) 0.034(3) 0.003(3) -0.004(3) 0.001(3) C19 0.076(5) 0.046(4) 0.030(3) -0.001(3) -0.008(3) 0.006(4) C20 0.070(5) 0.048(4) 0.047(4) 0.003(3) -0.019(3) 0.007(4) C21 0.062(5) 0.062(5) 0.067(5) 0.002(4) -0.012(4) 0.012(4) C22 0.077(5) 0.066(5) 0.057(4) -0.010(4) -0.002(4) 0.022(4) C23 0.070(5) 0.057(4) 0.038(3) -0.010(3) -0.005(3) 0.014(4) C24 0.067(5) 0.043(4) 0.036(3) -0.005(3) 0.002(3) 0.008(3) C25 0.100(7) 0.108(7) 0.052(4) 0.001(5) -0.033(4) 0.003(6) C26 0.078(6) 0.100(7) 0.110(7) -0.011(6) -0.026(5) 0.031(5) N5 0.062(4) 0.066(4) 0.053(4) 0.003(3) 0.001(3) -0.005(3) C27 0.062(12) 0.066(17) 0.053(19) 0.003(17) 0.001(16) -0.005(11) C28 0.062(11) 0.066(10) 0.053(11) 0.003(11) 0.001(11) -0.005(8) C29 0.062(11) 0.066(10) 0.053(11) 0.003(8) 0.001(8) -0.005(8) C30 0.062(10) 0.066(10) 0.053(10) 0.003(8) 0.001(8) -0.005(8) C31 0.062(15) 0.066(11) 0.053(13) 0.003(10) 0.001(9) -0.005(10) C32 0.062(11) 0.066(11) 0.053(12) 0.003(9) 0.001(9) -0.005(8) C33 0.062(13) 0.066(16) 0.053(11) 0.000 0.001(9) 0.000 C27' 0.062(16) 0.07(2) 0.05(2) 0.00(2) 0.00(2) -0.005(14) C28' 0.062(15) 0.066(13) 0.053(14) 0.003(14) 0.001(14) -0.005(11) C29' 0.062(12) 0.066(13) 0.053(13) 0.003(10) 0.001(10) -0.005(9) C30' 0.062(12) 0.066(12) 0.053(13) 0.003(9) 0.001(10) -0.005(10) C31' 0.062(18) 0.066(14) 0.053(16) 0.003(13) 0.001(12) -0.005(12) C32' 0.062(12) 0.066(14) 0.053(13) 0.003(10) 0.001(11) -0.005(10) C33' 0.062(19) 0.07(2) 0.053(18) 0.000 0.001(14) 0.000 _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 O2 2.122(4) 4_545 ? Mn1 O3 2.139(4) 4_545 ? Mn1 O1 2.158(4) . ? Mn1 O5 2.172(4) . ? Mn1 N5 2.229(6) . ? Mn1 N1 2.320(4) . ? Mn2 O4 2.108(4) 6_566 ? Mn2 O4 2.108(4) 4 ? Mn2 N4 2.241(5) 7_566 ? Mn2 N4 2.241(5) . ? Mn2 O8 2.252(5) 7_566 ? Mn2 O8 2.252(5) . ? N1 C4 1.337(7) . ? N1 C2 1.371(7) . ? N2 C4 1.353(7) . ? N2 C3 1.361(7) . ? N2 H2 0.8600 . ? N3 C17 1.358(7) . ? N3 C15 1.367(7) . ? N3 H3 0.8600 . ? N4 C17 1.339(7) . ? N4 C16 1.377(7) . ? O1 C1 1.268(6) . ? O2 C1 1.240(7) . ? O2 Mn1 2.122(4) 4 ? O3 C11 1.237(7) . ? O3 Mn1 2.139(4) 4 ? O4 C11 1.255(6) . ? O4 Mn2 2.108(4) 4_545 ? O5 C14 1.241(7) . ? O6 C14 1.266(8) . ? O6 H6A 0.8200 . ? O7 C24 1.273(8) . ? O8 C24 1.248(7) . ? C1 C2 1.497(7) . ? C2 C3 1.389(7) . ? C3 C11 1.500(8) . ? C4 C5 1.457(9) . ? C5 C6 1.390(8) . ? C5 C10 1.397(9) . ? C6 C7 1.360(10) . ? C6 H6 0.9300 . ? C7 C8 1.391(11) . ? C7 C12 1.521(10) . ? C7 H7 0.9300 . ? C8 C9 1.388(11) . ? C8 C13 1.520(10) . ? C9 C12' 1.34(3) . ? C9 C10 1.375(10) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.465(8) . ? C15 C16 1.375(7) . ? C16 C24 1.487(8) . ? C17 C18 1.444(8) . ? C18 C23 1.398(8) . ? C18 C19 1.402(7) . ? C19 C20 1.376(9) . ? C19 H19 0.9300 . ? C20 C21 1.385(10) . ? C20 C25 1.506(9) . ? C21 C22 1.403(9) . ? C21 C26 1.503(10) . ? C22 C23 1.377(9) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? N5 C31 1.32(3) . ? N5 C31' 1.33(3) . ? N5 C27' 1.33(8) . ? N5 C27 1.37(6) . ? C27 C28 1.38(6) . ? C27 H27 0.9300 . ? C28 C29 1.40(3) . ? C28 H28 0.9300 . ? C29 C30 1.30(2) . ? C29 C32 1.55(2) . ? C30 C31 1.40(3) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.40(2) . ? C32 C32 1.96(4) 2 ? C32 H32B 0.9700 . ? C32 H32A 0.9700 . ? C33 C32 1.40(2) 2 ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C27' C28' 1.38(8) . ? C27' H27' 0.9300 . ? C28' C29' 1.40(3) . ? C28' H28' 0.9300 . ? C29' C30' 1.26(3) . ? C29' C32' 1.50(3) . ? C30' C31' 1.37(4) . ? C30' H30' 0.9300 . ? C31' H31' 0.9300 . ? C32' C33' 1.60(2) . ? C32' H32C 0.9700 . ? C32' H32D 0.9700 . ? C33' C32' 1.60(2) 2 ? C33' H33C 0.9700 . ? C33' H33D 0.9700 . ? 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 Mn1 O3 86.53(16) 4_545 4_545 ? O2 Mn1 O1 90.27(17) 4_545 . ? O3 Mn1 O1 84.32(15) 4_545 . ? O2 Mn1 O5 176.62(17) 4_545 . ? O3 Mn1 O5 90.43(16) 4_545 . ? O1 Mn1 O5 90.91(17) . . ? O2 Mn1 N5 88.0(2) 4_545 . ? O3 Mn1 N5 89.19(19) 4_545 . ? O1 Mn1 N5 173.36(18) . . ? O5 Mn1 N5 90.5(2) . . ? O2 Mn1 N1 93.29(16) 4_545 . ? O3 Mn1 N1 157.76(17) 4_545 . ? O1 Mn1 N1 73.44(16) . . ? O5 Mn1 N1 90.09(17) . . ? N5 Mn1 N1 113.04(19) . . ? O4 Mn2 O4 180.00(10) 6_566 4 ? O4 Mn2 N4 88.50(16) 6_566 7_566 ? O4 Mn2 N4 91.50(16) 4 7_566 ? O4 Mn2 N4 91.50(16) 6_566 . ? O4 Mn2 N4 88.50(16) 4 . ? N4 Mn2 N4 180.000(1) 7_566 . ? O4 Mn2 O8 90.78(16) 6_566 7_566 ? O4 Mn2 O8 89.22(16) 4 7_566 ? N4 Mn2 O8 74.36(17) 7_566 7_566 ? N4 Mn2 O8 105.64(17) . 7_566 ? O4 Mn2 O8 89.22(16) 6_566 . ? O4 Mn2 O8 90.78(16) 4 . ? N4 Mn2 O8 105.64(17) 7_566 . ? N4 Mn2 O8 74.36(17) . . ? O8 Mn2 O8 180.000(1) 7_566 . ? C4 N1 C2 107.0(5) . . ? C4 N1 Mn1 142.0(4) . . ? C2 N1 Mn1 109.9(3) . . ? C4 N2 C3 110.1(4) . . ? C4 N2 H2 125.0 . . ? C3 N2 H2 125.0 . . ? C17 N3 C15 109.7(5) . . ? C17 N3 H3 125.1 . . ? C15 N3 H3 125.1 . . ? C17 N4 C16 106.2(5) . . ? C17 N4 Mn2 139.8(4) . . ? C16 N4 Mn2 109.2(4) . . ? C1 O1 Mn1 121.8(4) . . ? C1 O2 Mn1 134.9(4) . 4 ? C11 O3 Mn1 134.9(4) . 4 ? C11 O4 Mn2 140.2(4) . 4_545 ? C14 O5 Mn1 147.5(4) . . ? C14 O6 H6A 109.5 . . ? C24 O8 Mn2 113.7(4) . . ? O2 C1 O1 122.8(5) . . ? O2 C1 C2 122.4(5) . . ? O1 C1 C2 114.7(5) . . ? N1 C2 C3 109.5(5) . . ? N1 C2 C1 118.2(5) . . ? C3 C2 C1 132.2(6) . . ? N2 C3 C2 104.6(5) . . ? N2 C3 C11 118.7(5) . . ? C2 C3 C11 136.7(5) . . ? N1 C4 N2 108.9(5) . . ? N1 C4 C5 126.8(5) . . ? N2 C4 C5 124.2(5) . . ? C6 C5 C10 116.7(6) . . ? C6 C5 C4 123.3(6) . . ? C10 C5 C4 119.9(5) . . ? C7 C6 C5 123.3(7) . . ? C7 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? C6 C7 C8 119.5(6) . . ? C6 C7 C12 124.0(8) . . ? C8 C7 C12 116.4(7) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C12 C7 H7 4.9 . . ? C9 C8 C7 118.4(7) . . ? C9 C8 C13 119.5(8) . . ? C7 C8 C13 122.0(7) . . ? C12' C9 C10 116.8(16) . . ? C12' C9 C8 121.7(16) . . ? C10 C9 C8 121.4(8) . . ? C12' C9 H9 2.7 . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C5 120.5(7) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? O3 C11 O4 124.6(6) . . ? O3 C11 C3 121.3(5) . . ? O4 C11 C3 114.0(5) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? C9 C12' H12D 109.5 . . ? C9 C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C9 C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 O6 121.6(6) . . ? O5 C14 C15 121.0(6) . . ? O6 C14 C15 117.5(5) . . ? N3 C15 C16 104.6(5) . . ? N3 C15 C14 124.0(5) . . ? C16 C15 C14 131.4(6) . . ? C15 C16 N4 110.3(5) . . ? C15 C16 C24 132.1(6) . . ? N4 C16 C24 117.7(5) . . ? N4 C17 N3 109.1(5) . . ? N4 C17 C18 125.1(5) . . ? N3 C17 C18 125.7(5) . . ? C23 C18 C19 118.0(6) . . ? C23 C18 C17 122.6(5) . . ? C19 C18 C17 119.3(5) . . ? C20 C19 C18 121.8(6) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 120.3(6) . . ? C19 C20 C25 118.1(7) . . ? C21 C20 C25 121.6(7) . . ? C20 C21 C22 118.0(7) . . ? C20 C21 C26 123.1(7) . . ? C22 C21 C26 118.9(7) . . ? C23 C22 C21 122.1(7) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C18 119.7(6) . . ? C22 C23 H23 120.2 . . ? C18 C23 H23 120.2 . . ? O8 C24 O7 123.9(6) . . ? O8 C24 C16 118.0(6) . . ? O7 C24 C16 118.1(5) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C31 N5 C31' 27.6(9) . . ? C31 N5 C27' 108(3) . . ? C31' N5 C27' 111(3) . . ? C31 N5 C27 113(3) . . ? C31' N5 C27 124(3) . . ? C27' N5 C27 20(2) . . ? C31 N5 Mn1 127.7(12) . . ? C31' N5 Mn1 115.3(14) . . ? C27' N5 Mn1 124(3) . . ? C27 N5 Mn1 118(2) . . ? N5 C27 C28 123(4) . . ? N5 C27 H27 118.5 . . ? C28 C27 H27 118.5 . . ? C27 C28 C29 120(3) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 114.9(16) . . ? C30 C29 C32 123.4(16) . . ? C28 C29 C32 121.7(16) . . ? C29 C30 C31 123.2(17) . . ? C29 C30 H30 118.4 . . ? C31 C30 H30 118.4 . . ? N5 C31 C30 123(2) . . ? N5 C31 H31 118.5 . . ? C30 C31 H31 118.5 . . ? C33 C32 C29 135.5(14) . . ? C33 C32 C32 45.3(12) . 2 ? C29 C32 C32 112.2(12) . 2 ? C33 C32 H32B 103.3 . . ? C29 C32 H32B 103.3 . . ? C32 C32 H32B 143.9 2 . ? C33 C32 H32A 103.3 . . ? C29 C32 H32A 103.3 . . ? C32 C32 H32A 73.4 2 . ? H32B C32 H32A 105.2 . . ? C32 C33 C32 89(2) . 2 ? C32 C33 H33A 113.8 . . ? C32 C33 H33A 113.8 2 . ? C32 C33 H33B 113.8 . . ? C32 C33 H33B 113.8 2 . ? H33A C33 H33B 111.0 . . ? N5 C27' C28' 122(5) . . ? N5 C27' H27' 118.8 . . ? C28' C27' H27' 118.8 . . ? C27' C28' C29' 122(4) . . ? C27' C28' H28' 119.2 . . ? C29' C28' H28' 119.2 . . ? C30' C29' C28' 112(2) . . ? C30' C29' C32' 124.4(19) . . ? C28' C29' C32' 118(2) . . ? C29' C30' C31' 125(2) . . ? C29' C30' H30' 117.7 . . ? C31' C30' H30' 117.7 . . ? N5 C31' C30' 124(2) . . ? N5 C31' H31' 117.9 . . ? C30' C31' H31' 117.9 . . ? C29' C32' C33' 114.0(16) . . ? C29' C32' H32C 108.8 . . ? C33' C32' H32C 108.8 . . ? C29' C32' H32D 108.8 . . ? C33' C32' H32D 108.8 . . ? H32C C32' H32D 107.6 . . ? C32' C33' C32' 166(3) . 2 ? C32' C33' H33C 94.4 . . ? C32' C33' H33C 94.4 2 . ? C32' C33' H33D 94.4 . . ? C32' C33' H33D 94.4 2 . ? H33C C33' H33D 103.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O8 0.86 2.26 3.078(6) 159.5 6_565 N3 H3 O1 0.86 1.95 2.789(6) 165.7 . O6 H6A O7 0.82 1.63 2.454(6) 176.4 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.891 _refine_diff_density_min -2.063 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 937415'