# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_1 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 Cl2 Cu Mn N2 O15' _chemical_formula_weight 711.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.2278(13) _cell_length_b 10.2439(9) _cell_length_c 17.3848(14) _cell_angle_alpha 90.00 _cell_angle_beta 113.770(2) _cell_angle_gamma 90.00 _cell_volume 2644.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9810 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.55 _exptl_crystal_description parallelepiped _exptl_crystal_colour green _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 1.560 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9547 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33987 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6024 _reflns_number_gt 4835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0020P] 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 6024 _refine_ls_number_parameters 387 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1341 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.55669(17) 0.9550(2) 0.12826(19) 0.0397(6) Uani 1 1 d . . . C2 C 0.61920(19) 1.0377(3) 0.1879(2) 0.0476(7) Uani 1 1 d . . . C3 C 0.7059(2) 1.0514(3) 0.1925(2) 0.0584(9) Uani 1 1 d . . . H3 H 0.7469 1.1041 0.2338 0.070 Uiso 1 1 calc R . . C4 C 0.7320(2) 0.9866(4) 0.1354(3) 0.0657(10) Uani 1 1 d . . . H4 H 0.7896 0.9982 0.1372 0.079 Uiso 1 1 calc R . . C5 C 0.6721(2) 0.9055(3) 0.0767(2) 0.0567(8) Uani 1 1 d . . . H5 H 0.6897 0.8613 0.0391 0.068 Uiso 1 1 calc R . . C6 C 0.58425(18) 0.8880(3) 0.07237(19) 0.0436(6) Uani 1 1 d . . . C7 C 0.52848(19) 0.7932(3) 0.01347(19) 0.0453(6) Uani 1 1 d . . . H7 H 0.5549 0.7504 -0.0180 0.054 Uiso 1 1 calc R . . C8 C 0.4142(2) 0.6528(3) -0.0638(2) 0.0554(8) Uani 1 1 d . . . H8A H 0.4638 0.5948 -0.0573 0.067 Uiso 1 1 calc R . . H8B H 0.3924 0.6896 -0.1199 0.067 Uiso 1 1 calc R . . C9 C 0.3397(3) 0.5746(3) -0.0552(2) 0.0639(9) Uani 1 1 d . . . H9A H 0.3280 0.4978 -0.0907 0.077 Uiso 1 1 calc R . . H9B H 0.3591 0.5453 0.0025 0.077 Uiso 1 1 calc R . . C10 C 0.2541(2) 0.6517(3) -0.0792(2) 0.0630(9) Uani 1 1 d . . . H10A H 0.2412 0.6959 -0.1321 0.076 Uiso 1 1 calc R . . H10B H 0.2047 0.5924 -0.0871 0.076 Uiso 1 1 calc R . . C11 C 0.18527(18) 0.7706(3) -0.00786(17) 0.0439(6) Uani 1 1 d . . . H11 H 0.1358 0.7238 -0.0442 0.053 Uiso 1 1 calc R . . C12 C 0.16858(17) 0.8579(3) 0.04899(17) 0.0378(6) Uani 1 1 d . . . C13 C 0.08036(19) 0.8608(3) 0.0464(2) 0.0464(6) Uani 1 1 d . . . H13 H 0.0352 0.8119 0.0061 0.056 Uiso 1 1 calc R . . C14 C 0.06074(19) 0.9339(3) 0.1018(2) 0.0505(7) Uani 1 1 d . . . H14 H 0.0024 0.9354 0.0992 0.061 Uiso 1 1 calc R . . C15 C 0.1282(2) 1.0067(3) 0.1627(2) 0.0483(7) Uani 1 1 d . . . H15 H 0.1150 1.0556 0.2014 0.058 Uiso 1 1 calc R . . C16 C 0.21355(18) 1.0066(3) 0.16576(18) 0.0402(6) Uani 1 1 d . . . C17 C 0.23574(17) 0.9330(2) 0.10826(17) 0.0361(5) Uani 1 1 d . . . C18 C 0.6466(3) 1.1909(3) 0.2995(2) 0.0672(10) Uani 1 1 d . . . H18A H 0.6974 1.1445 0.3390 0.101 Uiso 1 1 calc R . . H18B H 0.6155 1.2343 0.3289 0.101 Uiso 1 1 calc R . . H18C H 0.6669 1.2542 0.2703 0.101 Uiso 1 1 calc R . . C19 C 0.2658(3) 1.1585(5) 0.2805(3) 0.0881(15) Uani 1 1 d . . . H19A H 0.2154 1.2135 0.2498 0.132 Uiso 1 1 calc R . . H19B H 0.3173 1.2116 0.3115 0.132 Uiso 1 1 calc R . . H19C H 0.2516 1.1047 0.3188 0.132 Uiso 1 1 calc R . . Cl1 Cl 0.65930(5) 0.14531(9) 0.54099(5) 0.0614(2) Uani 1 1 d . . . Cl2 Cl 0.02026(4) 0.91497(7) 0.71449(4) 0.04330(18) Uani 1 1 d . . . Cu1 Cu 0.37435(2) 0.83907(3) 0.05225(2) 0.03646(12) Uani 1 1 d . . . H5C H 0.442(3) 0.860(4) 0.333(2) 0.074(13) Uiso 1 1 d D . . H7C H 0.512(3) 1.107(5) 0.379(2) 0.117(19) Uiso 1 1 d D . . H5D H 0.476(3) 0.812(3) 0.286(3) 0.091(15) Uiso 1 1 d D . . H6D H 0.355(2) 1.277(5) 0.120(3) 0.122(19) Uiso 1 1 d D . . H7D H 0.461(5) 1.218(4) 0.349(4) 0.18(3) Uiso 1 1 d D . . Mn1 Mn 0.42728(3) 1.04484(4) 0.21151(3) 0.04156(14) Uani 1 1 d . . . N1 N 0.44786(15) 0.7597(2) -0.00158(14) 0.0406(5) Uani 1 1 d . . . N2 N 0.26016(15) 0.7491(2) -0.01463(14) 0.0429(5) Uani 1 1 d . . . O1 O 0.47486(12) 0.94466(17) 0.12713(12) 0.0422(4) Uani 1 1 d . . . O2 O 0.32042(12) 0.93751(18) 0.11523(12) 0.0414(4) Uani 1 1 d . . . O3 O 0.58653(14) 1.1002(2) 0.23994(15) 0.0567(5) Uani 1 1 d . . . O4 O 0.28567(13) 1.0766(2) 0.22261(15) 0.0534(5) Uani 1 1 d . . . O5 O 0.4646(2) 0.8824(3) 0.29880(17) 0.0706(7) Uani 1 1 d D . . O6 O 0.40062(17) 1.2388(2) 0.1557(2) 0.0659(6) Uani 1 1 d D . . O7 O 0.47322(19) 1.1427(3) 0.3347(2) 0.0830(9) Uani 1 1 d D . . O8 O 0.6226(5) 0.1645(5) 0.5971(3) 0.191(3) Uani 1 1 d . . . O9 O 0.6493(4) 0.2656(4) 0.4984(3) 0.1400(15) Uani 1 1 d . . . O10 O 0.7473(3) 0.1136(6) 0.5762(5) 0.224(4) Uani 1 1 d . . . O11 O 0.6128(3) 0.0489(3) 0.4821(3) 0.1175(13) Uani 1 1 d . . . O12 O 0.07733(17) 0.8888(3) 0.67228(18) 0.0772(8) Uani 1 1 d . . . O13 O 0.0549(2) 0.8550(3) 0.79451(18) 0.0887(9) Uani 1 1 d . . . O14 O -0.06768(16) 0.8642(3) 0.66816(17) 0.0756(8) Uani 1 1 d . . . O15 O 0.0182(2) 1.0509(2) 0.7273(2) 0.0915(9) Uani 1 1 d . . . H6C H 0.428(3) 1.267(5) 0.2035(18) 0.12(2) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0343(12) 0.0321(13) 0.0507(17) 0.0062(11) 0.0149(12) 0.0008(10) C2 0.0392(14) 0.0402(15) 0.0556(18) 0.0047(13) 0.0110(13) -0.0004(11) C3 0.0375(15) 0.0492(18) 0.075(2) 0.0064(16) 0.0088(16) -0.0083(12) C4 0.0355(15) 0.066(2) 0.092(3) 0.019(2) 0.0218(18) 0.0007(14) C5 0.0476(16) 0.0523(18) 0.079(2) 0.0124(16) 0.0342(17) 0.0069(14) C6 0.0415(14) 0.0386(14) 0.0552(17) 0.0063(12) 0.0241(13) 0.0002(11) C7 0.0532(16) 0.0407(14) 0.0506(17) 0.0002(13) 0.0297(14) 0.0040(12) C8 0.067(2) 0.0526(18) 0.0536(19) -0.0181(14) 0.0312(17) -0.0042(14) C9 0.086(2) 0.0448(17) 0.069(2) -0.0212(16) 0.039(2) -0.0129(16) C10 0.063(2) 0.066(2) 0.063(2) -0.0345(17) 0.0288(18) -0.0240(16) C11 0.0435(14) 0.0486(15) 0.0346(14) -0.0047(12) 0.0106(12) -0.0139(12) C12 0.0368(13) 0.0381(13) 0.0353(14) 0.0046(11) 0.0112(11) -0.0016(10) C13 0.0384(14) 0.0482(15) 0.0493(17) 0.0079(13) 0.0144(13) -0.0039(12) C14 0.0387(14) 0.0516(16) 0.063(2) 0.0136(14) 0.0224(14) 0.0051(12) C15 0.0522(16) 0.0424(15) 0.0611(19) 0.0014(13) 0.0341(15) 0.0039(12) C16 0.0425(14) 0.0376(13) 0.0416(15) -0.0015(11) 0.0180(12) 0.0010(11) C17 0.0364(13) 0.0329(12) 0.0390(14) 0.0032(10) 0.0152(11) 0.0012(10) C18 0.073(2) 0.0526(18) 0.054(2) -0.0096(16) 0.0035(17) -0.0165(17) C19 0.069(2) 0.115(4) 0.090(3) -0.062(3) 0.042(2) -0.013(2) Cl1 0.0511(4) 0.0738(6) 0.0539(5) -0.0127(4) 0.0156(4) 0.0019(4) Cl2 0.0434(3) 0.0411(3) 0.0469(4) -0.0002(3) 0.0198(3) -0.0034(3) Cu1 0.0386(2) 0.03489(19) 0.0380(2) -0.00892(12) 0.01764(15) -0.00670(12) Mn1 0.0413(2) 0.0366(2) 0.0416(3) -0.01056(17) 0.01138(19) -0.00106(16) N1 0.0512(13) 0.0352(11) 0.0404(13) -0.0008(9) 0.0237(11) 0.0007(9) N2 0.0458(12) 0.0430(12) 0.0394(13) -0.0108(10) 0.0167(10) -0.0115(10) O1 0.0377(9) 0.0414(10) 0.0491(12) -0.0114(8) 0.0193(9) -0.0080(7) O2 0.0346(9) 0.0465(10) 0.0459(11) -0.0160(8) 0.0191(8) -0.0060(8) O3 0.0477(11) 0.0507(12) 0.0607(14) -0.0163(11) 0.0105(10) -0.0105(10) O4 0.0480(11) 0.0577(12) 0.0607(14) -0.0257(10) 0.0285(10) -0.0078(9) O5 0.098(2) 0.0564(15) 0.0664(17) 0.0038(13) 0.0426(16) 0.0238(14) O6 0.0557(14) 0.0483(13) 0.085(2) 0.0049(13) 0.0189(14) 0.0045(11) O7 0.0682(17) 0.090(2) 0.0655(18) -0.0425(16) 0.0011(14) 0.0194(15) O8 0.345(8) 0.145(4) 0.182(5) -0.011(3) 0.211(6) -0.012(4) O9 0.227(5) 0.090(3) 0.108(3) 0.003(2) 0.073(3) -0.013(3) O10 0.064(2) 0.177(5) 0.320(8) -0.097(5) -0.037(4) 0.022(3) O11 0.110(3) 0.090(2) 0.112(3) -0.031(2) 0.004(2) -0.0079(19) O12 0.0654(15) 0.0977(19) 0.0861(19) -0.0228(16) 0.0488(15) -0.0153(14) O13 0.0844(19) 0.108(2) 0.0615(17) 0.0337(15) 0.0170(15) -0.0080(16) O14 0.0464(12) 0.099(2) 0.0780(18) -0.0279(15) 0.0217(12) -0.0155(12) O15 0.103(2) 0.0418(14) 0.130(3) -0.0009(14) 0.047(2) 0.0047(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.324(3) . ? C1 C6 1.402(4) . ? C1 C2 1.406(4) . ? C2 O3 1.376(4) . ? C2 C3 1.384(4) . ? C3 C4 1.395(5) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4 0.9300 . ? C5 C6 1.408(4) . ? C5 H5 0.9300 . ? C6 C7 1.436(4) . ? C7 N1 1.274(3) . ? C7 H7 0.9300 . ? C8 N1 1.480(4) . ? C8 C9 1.507(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.504(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.475(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.286(3) . ? C11 C12 1.437(4) . ? C11 H11 0.9300 . ? C12 C17 1.391(4) . ? C12 C13 1.414(4) . ? C13 C14 1.356(5) . ? C13 H13 0.9300 . ? C14 C15 1.393(5) . ? C14 H14 0.9300 . ? C15 C16 1.365(4) . ? C15 H15 0.9300 . ? C16 O4 1.389(3) . ? C16 C17 1.410(4) . ? C17 O2 1.331(3) . ? C18 O3 1.439(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O4 1.443(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? Cl1 O8 1.346(4) . ? Cl1 O10 1.347(4) . ? Cl1 O11 1.403(3) . ? Cl1 O9 1.413(4) . ? Cl2 O15 1.412(3) . ? Cl2 O13 1.414(3) . ? Cl2 O12 1.420(2) . ? Cl2 O14 1.425(2) . ? Cu1 O2 1.9376(17) . ? Cu1 O1 1.9528(18) . ? Cu1 N1 1.964(2) . ? Cu1 N2 1.974(2) . ? Mn1 O2 2.1628(18) . ? Mn1 O5 2.167(3) . ? Mn1 O1 2.1712(18) . ? Mn1 O6 2.177(3) . ? Mn1 O7 2.205(3) . ? Mn1 O4 2.4044(19) . ? Mn1 O3 2.493(2) . ? O5 H5C 0.838(19) . ? O5 H5D 0.803(19) . ? O6 H6D 0.838(19) . ? O6 H6C 0.821(19) . ? O7 H7C 0.859(19) . ? O7 H7D 0.86(2) . ? 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 C6 123.3(2) . . ? O1 C1 C2 118.7(2) . . ? C6 C1 C2 118.0(2) . . ? O3 C2 C3 124.5(3) . . ? O3 C2 C1 114.3(2) . . ? C3 C2 C1 121.2(3) . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 120.0(3) . . ? C1 C6 C7 122.7(2) . . ? C5 C6 C7 117.2(3) . . ? N1 C7 C6 128.9(3) . . ? N1 C7 H7 115.5 . . ? C6 C7 H7 115.5 . . ? N1 C8 C9 113.3(3) . . ? N1 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N1 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 112.4(3) . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9B 109.1 . . ? C8 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? N2 C10 C9 111.9(3) . . ? N2 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? N2 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N2 C11 C12 128.0(2) . . ? N2 C11 H11 116.0 . . ? C12 C11 H11 116.0 . . ? C17 C12 C13 119.5(3) . . ? C17 C12 C11 123.0(2) . . ? C13 C12 C11 117.4(2) . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 O4 125.3(3) . . ? C15 C16 C17 121.2(3) . . ? O4 C16 C17 113.5(2) . . ? O2 C17 C12 123.9(2) . . ? O2 C17 C16 117.8(2) . . ? C12 C17 C16 118.2(2) . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O8 Cl1 O10 113.8(4) . . ? O8 Cl1 O11 111.4(3) . . ? O10 Cl1 O11 108.8(3) . . ? O8 Cl1 O9 105.2(3) . . ? O10 Cl1 O9 108.9(4) . . ? O11 Cl1 O9 108.5(3) . . ? O15 Cl2 O13 107.3(2) . . ? O15 Cl2 O12 109.27(19) . . ? O13 Cl2 O12 110.07(19) . . ? O15 Cl2 O14 111.55(18) . . ? O13 Cl2 O14 107.94(19) . . ? O12 Cl2 O14 110.63(16) . . ? O2 Cu1 O1 77.35(7) . . ? O2 Cu1 N1 169.69(8) . . ? O1 Cu1 N1 92.44(9) . . ? O2 Cu1 N2 92.59(8) . . ? O1 Cu1 N2 169.93(8) . . ? N1 Cu1 N2 97.60(9) . . ? O2 Mn1 O5 93.56(10) . . ? O2 Mn1 O1 68.24(6) . . ? O5 Mn1 O1 92.01(9) . . ? O2 Mn1 O6 99.54(10) . . ? O5 Mn1 O6 164.19(11) . . ? O1 Mn1 O6 101.02(10) . . ? O2 Mn1 O7 146.59(10) . . ? O5 Mn1 O7 77.25(12) . . ? O1 Mn1 O7 142.95(9) . . ? O6 Mn1 O7 86.94(13) . . ? O2 Mn1 O4 68.71(7) . . ? O5 Mn1 O4 93.10(10) . . ? O1 Mn1 O4 136.87(7) . . ? O6 Mn1 O4 83.54(9) . . ? O7 Mn1 O4 79.65(9) . . ? O2 Mn1 O3 135.46(7) . . ? O5 Mn1 O3 93.51(10) . . ? O1 Mn1 O3 67.60(7) . . ? O6 Mn1 O3 83.37(9) . . ? O7 Mn1 O3 77.66(10) . . ? O4 Mn1 O3 154.31(7) . . ? C7 N1 C8 113.3(2) . . ? C7 N1 Cu1 124.2(2) . . ? C8 N1 Cu1 122.56(18) . . ? C11 N2 C10 114.2(2) . . ? C11 N2 Cu1 124.28(19) . . ? C10 N2 Cu1 121.54(19) . . ? C1 O1 Cu1 128.10(17) . . ? C1 O1 Mn1 125.44(17) . . ? Cu1 O1 Mn1 106.46(8) . . ? C17 O2 Cu1 127.99(16) . . ? C17 O2 Mn1 124.37(16) . . ? Cu1 O2 Mn1 107.34(8) . . ? C2 O3 C18 116.4(3) . . ? C2 O3 Mn1 114.00(16) . . ? C18 O3 Mn1 129.5(2) . . ? C16 O4 C19 115.8(2) . . ? C16 O4 Mn1 115.55(15) . . ? C19 O4 Mn1 128.6(2) . . ? Mn1 O5 H5C 128(3) . . ? Mn1 O5 H5D 122(3) . . ? H5C O5 H5D 100(4) . . ? Mn1 O6 H6D 135(4) . . ? Mn1 O6 H6C 87(4) . . ? H6D O6 H6C 122(5) . . ? Mn1 O7 H7C 121(4) . . ? Mn1 O7 H7D 132(5) . . ? H7C O7 H7D 107(5) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.482 _refine_diff_density_min -0.632 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 930928' ####################################################################### # # 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_global # Attachment '2.cif' data_2 #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 Cl2 Cu Fe N2 O15' _chemical_formula_weight 712.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.3338(10) _cell_length_b 10.1930(7) _cell_length_c 17.2984(12) _cell_angle_alpha 90.00 _cell_angle_beta 114.814(2) _cell_angle_gamma 90.00 _cell_volume 2614.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9970 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 30.04 _exptl_crystal_description parallelepiped _exptl_crystal_colour green _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 1.651 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9220 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31398 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.00 _reflns_number_total 6276 _reflns_number_gt 5331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0200P] 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 6276 _refine_ls_number_parameters 387 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1455 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _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 C17 C 0.73652(16) 0.0684(2) 0.60866(14) 0.0336(5) Uani 1 1 d . . . C16 C 0.71480(18) -0.0047(3) 0.66678(17) 0.0395(5) Uani 1 1 d . . . C15 C 0.6293(2) -0.0041(3) 0.6629(2) 0.0471(6) Uani 1 1 d . . . H15 H 0.6164 -0.0531 0.7018 0.056 Uiso 1 1 calc R . . C14 C 0.56187(19) 0.0694(3) 0.6011(2) 0.0497(6) Uani 1 1 d . . . H14 H 0.5037 0.0686 0.5981 0.060 Uiso 1 1 calc R . . C13 C 0.58106(18) 0.1427(3) 0.54494(18) 0.0452(6) Uani 1 1 d . . . H13 H 0.5357 0.1920 0.5039 0.054 Uiso 1 1 calc R . . C12 C 0.66873(16) 0.1447(2) 0.54812(15) 0.0360(5) Uani 1 1 d . . . C11 C 0.68498(17) 0.2324(3) 0.49042(15) 0.0414(5) Uani 1 1 d . . . H11 H 0.6353 0.2796 0.4532 0.050 Uiso 1 1 calc R . . C10 C 0.7529(2) 0.3516(3) 0.4187(2) 0.0589(8) Uani 1 1 d . . . H10A H 0.7037 0.4115 0.4103 0.071 Uiso 1 1 calc R . . H10B H 0.7395 0.3073 0.3651 0.071 Uiso 1 1 calc R . . C9 C 0.8392(2) 0.4283(3) 0.4443(2) 0.0583(8) Uani 1 1 d . . . H9A H 0.8277 0.5058 0.4087 0.070 Uiso 1 1 calc R . . H9B H 0.8594 0.4571 0.5028 0.070 Uiso 1 1 calc R . . C8 C 0.9118(2) 0.3487(3) 0.4359(2) 0.0543(7) Uani 1 1 d . . . H8A H 0.8887 0.3117 0.3790 0.065 Uiso 1 1 calc R . . H8B H 0.9617 0.4060 0.4425 0.065 Uiso 1 1 calc R . . C7 C 1.02655(19) 0.2058(3) 0.51436(18) 0.0442(6) Uani 1 1 d . . . H7 H 1.0526 0.2477 0.4824 0.053 Uiso 1 1 calc R . . C6 C 1.08223(17) 0.1106(3) 0.57448(18) 0.0418(5) Uani 1 1 d . . . C5 C 1.1691(2) 0.0915(3) 0.5785(2) 0.0561(7) Uani 1 1 d . . . H5 H 1.1861 0.1355 0.5405 0.067 Uiso 1 1 calc R . . C4 C 1.2292(2) 0.0087(3) 0.6378(3) 0.0632(9) Uani 1 1 d . . . H4 H 1.2862 -0.0044 0.6394 0.076 Uiso 1 1 calc R . . C3 C 1.2041(2) -0.0555(3) 0.6956(2) 0.0563(8) Uani 1 1 d . . . H3 H 1.2454 -0.1088 0.7375 0.068 Uiso 1 1 calc R . . C2 C 1.11837(18) -0.0406(3) 0.69103(18) 0.0451(6) Uani 1 1 d . . . C1 C 1.05551(16) 0.0430(2) 0.63041(16) 0.0375(5) Uani 1 1 d . . . C19 C 0.7682(3) -0.1545(5) 0.7831(3) 0.0857(14) Uani 1 1 d . . . H19A H 0.7472 -0.1002 0.8164 0.129 Uiso 1 1 calc R . . H19B H 0.8222 -0.1992 0.8201 0.129 Uiso 1 1 calc R . . H19C H 0.7226 -0.2177 0.7522 0.129 Uiso 1 1 calc R . . C18 C 1.1462(2) -0.1961(3) 0.8019(2) 0.0650(9) Uani 1 1 d . . . H18A H 1.1638 -0.2612 0.7718 0.097 Uiso 1 1 calc R . . H18B H 1.1161 -0.2378 0.8326 0.097 Uiso 1 1 calc R . . H18C H 1.1987 -0.1508 0.8413 0.097 Uiso 1 1 calc R . . Cl1 Cl 0.01794(4) 0.41839(6) 0.71493(4) 0.04104(16) Uani 1 1 d . . . Cl2 Cl 0.65794(5) 0.64785(9) 0.54005(5) 0.0593(2) Uani 1 1 d . . . Cu1 Cu 0.873566(19) 0.16235(3) 0.552723(17) 0.03424(12) Uani 1 1 d . . . Fe1 Fe 0.92572(2) -0.04311(3) 0.71012(2) 0.03993(13) Uani 1 1 d . . . H5C H 0.8496(17) -0.262(4) 0.631(3) 0.083(14) Uiso 1 1 d D . . H6C H 0.980(3) 0.190(3) 0.786(3) 0.094(15) Uiso 1 1 d D . . H7C H 1.015(3) -0.100(6) 0.864(3) 0.14(2) Uiso 1 1 d D . . H5D H 0.938(2) -0.276(4) 0.688(2) 0.080(13) Uiso 1 1 d D . . H6D H 0.941(2) 0.129(4) 0.831(2) 0.065(12) Uiso 1 1 d D . . H7D H 0.953(3) -0.213(3) 0.843(3) 0.074(12) Uiso 1 1 d D . . N2 N 0.75936(14) 0.2531(2) 0.48415(13) 0.0399(5) Uani 1 1 d . . . N1 N 0.94565(15) 0.2412(2) 0.49859(13) 0.0391(4) Uani 1 1 d . . . O2 O 0.82064(11) 0.06362(17) 0.61563(11) 0.0395(4) Uani 1 1 d . . . O1 O 0.97407(12) 0.05456(17) 0.62949(12) 0.0401(4) Uani 1 1 d . . . O4 O 0.78684(14) -0.0743(2) 0.72423(15) 0.0546(5) Uani 1 1 d . . . O3 O 1.08634(14) -0.1043(2) 0.74261(14) 0.0574(5) Uani 1 1 d . . . O5 O 0.89895(17) -0.2302(2) 0.65166(19) 0.0649(6) Uani 1 1 d D . . O6 O 0.96432(19) 0.1173(3) 0.79810(15) 0.0645(6) Uani 1 1 d D . . O7 O 0.97117(18) -0.1436(3) 0.82779(18) 0.0755(8) Uani 1 1 d D . . O8 O 0.07576(18) 0.3898(3) 0.67443(18) 0.0771(8) Uani 1 1 d . . . O9 O 0.0542(2) 0.3601(3) 0.79683(18) 0.0901(9) Uani 1 1 d . . . O10 O 0.0133(2) 0.5542(3) 0.7251(3) 0.0991(11) Uani 1 1 d . . . O11 O -0.06897(16) 0.3614(3) 0.66969(18) 0.0742(7) Uani 1 1 d . . . O12 O 0.6088(3) 0.5517(3) 0.4800(3) 0.1129(13) Uani 1 1 d . . . O13 O 0.7464(3) 0.6126(6) 0.5736(4) 0.190(3) Uani 1 1 d . . . O14 O 0.6266(5) 0.6654(5) 0.6016(3) 0.168(2) Uani 1 1 d . . . O15 O 0.6471(4) 0.7704(4) 0.4975(3) 0.1254(14) 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 C17 0.0335(12) 0.0321(11) 0.0330(10) -0.0008(8) 0.0117(9) -0.0011(8) C16 0.0406(13) 0.0364(12) 0.0433(13) 0.0023(10) 0.0194(11) -0.0026(9) C15 0.0483(15) 0.0441(14) 0.0566(16) -0.0027(12) 0.0296(13) -0.0048(11) C14 0.0375(13) 0.0532(16) 0.0594(16) -0.0109(13) 0.0212(12) -0.0048(11) C13 0.0339(13) 0.0512(15) 0.0445(13) -0.0063(11) 0.0105(11) 0.0027(10) C12 0.0323(11) 0.0364(12) 0.0335(11) -0.0050(9) 0.0082(9) 0.0010(9) C11 0.0394(13) 0.0457(13) 0.0312(11) 0.0037(9) 0.0072(10) 0.0122(10) C10 0.0607(19) 0.0664(19) 0.0524(16) 0.0322(14) 0.0264(15) 0.0247(15) C9 0.079(2) 0.0436(15) 0.0585(17) 0.0172(13) 0.0347(16) 0.0107(14) C8 0.0629(19) 0.0559(17) 0.0516(16) 0.0196(13) 0.0313(15) 0.0034(13) C7 0.0502(15) 0.0415(13) 0.0485(14) -0.0027(11) 0.0283(12) -0.0053(11) C6 0.0393(13) 0.0364(12) 0.0521(14) -0.0063(10) 0.0216(11) -0.0015(10) C5 0.0456(16) 0.0554(17) 0.075(2) -0.0157(15) 0.0327(15) -0.0084(13) C4 0.0336(15) 0.063(2) 0.089(2) -0.0163(17) 0.0215(16) 0.0011(13) C3 0.0336(14) 0.0511(16) 0.0680(19) -0.0068(14) 0.0055(13) 0.0069(11) C2 0.0374(13) 0.0403(13) 0.0473(14) -0.0045(10) 0.0077(11) 0.0024(10) C1 0.0299(11) 0.0330(11) 0.0433(13) -0.0065(9) 0.0093(10) -0.0001(8) C19 0.070(2) 0.104(3) 0.088(3) 0.059(3) 0.039(2) 0.011(2) C18 0.065(2) 0.0517(17) 0.0533(17) 0.0085(14) -0.0003(15) 0.0158(15) Cl1 0.0407(3) 0.0408(3) 0.0417(3) 0.0001(2) 0.0174(3) -0.0041(2) Cl2 0.0470(4) 0.0748(5) 0.0488(4) -0.0127(3) 0.0130(3) 0.0026(3) Cu1 0.03503(19) 0.03416(18) 0.03368(18) 0.00835(10) 0.01457(13) 0.00608(10) Fe1 0.0399(2) 0.0354(2) 0.0373(2) 0.01036(13) 0.00919(16) 0.00072(13) N2 0.0421(11) 0.0435(11) 0.0328(10) 0.0104(8) 0.0144(9) 0.0092(9) N1 0.0470(12) 0.0348(10) 0.0380(10) 0.0017(8) 0.0203(9) -0.0001(8) O2 0.0325(9) 0.0447(10) 0.0424(9) 0.0155(7) 0.0166(7) 0.0066(7) O1 0.0331(9) 0.0411(9) 0.0457(9) 0.0102(7) 0.0161(7) 0.0067(7) O4 0.0466(11) 0.0610(12) 0.0599(12) 0.0277(10) 0.0260(10) 0.0080(9) O3 0.0479(11) 0.0565(13) 0.0565(12) 0.0163(10) 0.0108(9) 0.0119(9) O5 0.0513(14) 0.0454(12) 0.0856(17) -0.0035(11) 0.0166(13) -0.0041(10) O6 0.0878(18) 0.0544(13) 0.0567(13) -0.0021(10) 0.0356(13) -0.0199(12) O7 0.0608(15) 0.0771(17) 0.0651(15) 0.0411(13) 0.0034(12) -0.0119(12) O8 0.0640(15) 0.098(2) 0.0865(18) -0.0221(16) 0.0484(15) -0.0159(14) O9 0.0800(19) 0.122(3) 0.0558(14) 0.0317(16) 0.0165(13) -0.0049(17) O10 0.105(2) 0.0452(15) 0.147(3) 0.0009(16) 0.053(2) 0.0033(14) O11 0.0472(13) 0.0965(19) 0.0762(16) -0.0352(14) 0.0233(12) -0.0204(12) O12 0.102(3) 0.088(2) 0.102(3) -0.0249(19) -0.004(2) -0.0097(18) O13 0.055(2) 0.170(5) 0.266(7) -0.081(5) -0.010(3) 0.016(2) O14 0.284(7) 0.149(4) 0.152(4) -0.006(3) 0.170(5) -0.009(4) O15 0.197(4) 0.085(2) 0.098(3) -0.002(2) 0.066(3) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C17 O2 1.329(3) . ? C17 C12 1.398(3) . ? C17 C16 1.411(3) . ? C16 C15 1.369(4) . ? C16 O4 1.377(3) . ? C15 C14 1.389(4) . ? C15 H15 0.9300 . ? C14 C13 1.362(4) . ? C14 H14 0.9300 . ? C13 C12 1.410(4) . ? C13 H13 0.9300 . ? C12 C11 1.445(4) . ? C11 N2 1.282(4) . ? C11 H11 0.9300 . ? C10 N2 1.482(3) . ? C10 C9 1.507(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9 C8 1.494(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8 N1 1.476(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 N1 1.284(4) . ? C7 C6 1.434(4) . ? C7 H7 0.9300 . ? C6 C1 1.399(4) . ? C6 C5 1.404(4) . ? C5 C4 1.372(5) . ? C5 H5 0.9300 . ? C4 C3 1.392(5) . ? C4 H4 0.9300 . ? C3 C2 1.377(4) . ? C3 H3 0.9300 . ? C2 O3 1.372(4) . ? C2 C1 1.406(4) . ? C1 O1 1.329(3) . ? C19 O4 1.434(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18 O3 1.429(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? Cl1 O10 1.401(3) . ? Cl1 O9 1.417(3) . ? Cl1 O8 1.422(2) . ? Cl1 O11 1.425(2) . ? Cl2 O13 1.360(4) . ? Cl2 O14 1.373(4) . ? Cl2 O12 1.409(3) . ? Cl2 O15 1.422(4) . ? Cu1 O2 1.9323(17) . ? Cu1 N1 1.958(2) . ? Cu1 O1 1.9585(17) . ? Cu1 N2 1.971(2) . ? Fe1 O2 2.1086(17) . ? Fe1 O7 2.116(2) . ? Fe1 O5 2.117(2) . ? Fe1 O1 2.1178(18) . ? Fe1 O6 2.140(3) . ? Fe1 O4 2.402(2) . ? Fe1 O3 2.520(2) . ? O5 H5C 0.799(19) . ? O5 H5D 0.829(19) . ? O6 H6C 0.843(19) . ? O6 H6D 0.818(19) . ? O7 H7C 0.85(2) . ? O7 H7D 0.848(19) . ? 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 C17 C12 123.5(2) . . ? O2 C17 C16 118.4(2) . . ? C12 C17 C16 118.1(2) . . ? C15 C16 O4 125.6(2) . . ? C15 C16 C17 121.3(3) . . ? O4 C16 C17 113.1(2) . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C13 C12 120.9(3) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C17 C12 C13 119.6(2) . . ? C17 C12 C11 123.0(2) . . ? C13 C12 C11 117.4(2) . . ? N2 C11 C12 128.0(2) . . ? N2 C11 H11 116.0 . . ? C12 C11 H11 116.0 . . ? N2 C10 C9 111.7(3) . . ? N2 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C8 C9 C10 111.9(3) . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N1 C8 C9 113.6(2) . . ? N1 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N1 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N1 C7 C6 128.8(3) . . ? N1 C7 H7 115.6 . . ? C6 C7 H7 115.6 . . ? C1 C6 C5 119.9(3) . . ? C1 C6 C7 123.2(2) . . ? C5 C6 C7 116.8(3) . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C2 C3 C4 120.3(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? O3 C2 C3 124.5(3) . . ? O3 C2 C1 114.4(2) . . ? C3 C2 C1 121.1(3) . . ? O1 C1 C6 123.3(2) . . ? O1 C1 C2 118.5(2) . . ? C6 C1 C2 118.2(2) . . ? O4 C19 H19A 109.5 . . ? O4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C18 H18A 109.5 . . ? O3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O10 Cl1 O9 108.1(2) . . ? O10 Cl1 O8 110.3(2) . . ? O9 Cl1 O8 108.7(2) . . ? O10 Cl1 O11 112.1(2) . . ? O9 Cl1 O11 106.28(19) . . ? O8 Cl1 O11 111.12(16) . . ? O13 Cl2 O14 112.3(4) . . ? O13 Cl2 O12 107.8(3) . . ? O14 Cl2 O12 112.3(3) . . ? O13 Cl2 O15 109.4(4) . . ? O14 Cl2 O15 106.3(3) . . ? O12 Cl2 O15 108.7(2) . . ? O2 Cu1 N1 169.72(8) . . ? O2 Cu1 O1 76.81(7) . . ? N1 Cu1 O1 93.06(8) . . ? O2 Cu1 N2 92.83(8) . . ? N1 Cu1 N2 97.27(9) . . ? O1 Cu1 N2 169.61(8) . . ? O2 Fe1 O7 146.99(10) . . ? O2 Fe1 O5 99.02(9) . . ? O7 Fe1 O5 86.68(12) . . ? O2 Fe1 O1 69.76(7) . . ? O7 Fe1 O1 141.63(9) . . ? O5 Fe1 O1 99.69(10) . . ? O2 Fe1 O6 93.34(9) . . ? O7 Fe1 O6 78.81(11) . . ? O5 Fe1 O6 165.49(11) . . ? O1 Fe1 O6 91.68(9) . . ? O2 Fe1 O4 69.57(7) . . ? O7 Fe1 O4 78.65(9) . . ? O5 Fe1 O4 85.10(10) . . ? O1 Fe1 O4 139.31(7) . . ? O6 Fe1 O4 92.17(10) . . ? O2 Fe1 O3 137.15(7) . . ? O7 Fe1 O3 75.72(10) . . ? O5 Fe1 O3 82.55(9) . . ? O1 Fe1 O3 67.80(7) . . ? O6 Fe1 O3 93.56(10) . . ? O4 Fe1 O3 152.08(7) . . ? C11 N2 C10 114.2(2) . . ? C11 N2 Cu1 124.24(17) . . ? C10 N2 Cu1 121.55(19) . . ? C7 N1 C8 113.5(2) . . ? C7 N1 Cu1 123.71(19) . . ? C8 N1 Cu1 122.74(19) . . ? C17 O2 Cu1 128.29(14) . . ? C17 O2 Fe1 124.30(14) . . ? Cu1 O2 Fe1 107.12(8) . . ? C1 O1 Cu1 127.42(16) . . ? C1 O1 Fe1 126.78(16) . . ? Cu1 O1 Fe1 105.79(8) . . ? C16 O4 C19 115.8(2) . . ? C16 O4 Fe1 114.57(15) . . ? C19 O4 Fe1 129.7(2) . . ? C2 O3 C18 116.4(3) . . ? C2 O3 Fe1 112.52(15) . . ? C18 O3 Fe1 131.0(2) . . ? Fe1 O5 H5C 123(3) . . ? Fe1 O5 H5D 102(3) . . ? H5C O5 H5D 115(5) . . ? Fe1 O6 H6C 121(3) . . ? Fe1 O6 H6D 121(3) . . ? H6C O6 H6D 110(4) . . ? Fe1 O7 H7C 107(5) . . ? Fe1 O7 H7D 132(3) . . ? H7C O7 H7D 120(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.802 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.101 _database_code_depnum_ccdc_archive 'CCDC 930929' ####################################################################### # # 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_global # Attachment '3.cif' data_3 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C69 H68 Cl2 Cu3 Mn N6 O24' _chemical_formula_weight 1681.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.5653(15) _cell_length_b 26.500(3) _cell_length_c 22.771(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.591(2) _cell_angle_gamma 90.00 _cell_volume 6945.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9974 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.23 _exptl_crystal_description hexagonal _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3448 _exptl_absorpt_coefficient_mu 1.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7216 _exptl_absorpt_correction_T_max 0.7710 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47594 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.25 _reflns_number_total 12484 _reflns_number_gt 9145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^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 12484 _refine_ls_number_parameters 975 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.942 _refine_ls_restrained_S_all 0.942 _refine_ls_shift/su_max 0.002 _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 0.8078(3) 0.54795(12) 0.83551(14) 0.0387(7) Uani 1 1 d . . . C2 C 0.7733(3) 0.49771(13) 0.84536(15) 0.0477(8) Uani 1 1 d . . . C3 C 0.8031(4) 0.47427(15) 0.89826(17) 0.0595(10) Uani 1 1 d . . . H3 H 0.7793 0.4413 0.9043 0.071 Uiso 1 1 calc R . . C4 C 0.8692(4) 0.50000(16) 0.94298(17) 0.0617(11) Uani 1 1 d . . . H4 H 0.8887 0.4842 0.9790 0.074 Uiso 1 1 calc R . . C5 C 0.9053(3) 0.54745(15) 0.93478(15) 0.0534(9) Uani 1 1 d . . . H5A H 0.9498 0.5639 0.9652 0.064 Uiso 1 1 calc R . . C6 C 0.8767(3) 0.57286(12) 0.88060(14) 0.0415(8) Uani 1 1 d . . . C7 C 0.9206(3) 0.62333(12) 0.87528(15) 0.0432(8) Uani 1 1 d . . . H7 H 0.9651 0.6366 0.9079 0.052 Uiso 1 1 calc R . . C8 C 0.9502(3) 0.70120(12) 0.82691(15) 0.0409(8) Uani 1 1 d . . . C9 C 1.0222(3) 0.72443(14) 0.87124(16) 0.0497(9) Uani 1 1 d . . . H9 H 1.0438 0.7074 0.9063 0.060 Uiso 1 1 calc R . . C10 C 1.0614(3) 0.77231(14) 0.86344(18) 0.0573(10) Uani 1 1 d . . . H10 H 1.1098 0.7877 0.8932 0.069 Uiso 1 1 calc R . . C11 C 1.0296(4) 0.79788(14) 0.8119(2) 0.0613(11) Uani 1 1 d . . . H11 H 1.0553 0.8308 0.8074 0.074 Uiso 1 1 calc R . . C12 C 0.9603(3) 0.77550(13) 0.76676(17) 0.0514(9) Uani 1 1 d . . . H12 H 0.9406 0.7929 0.7318 0.062 Uiso 1 1 calc R . . C13 C 0.9200(3) 0.72682(12) 0.77361(14) 0.0404(8) Uani 1 1 d . . . C14 C 0.8153(3) 0.71608(12) 0.67838(14) 0.0391(7) Uani 1 1 d . . . H14 H 0.8401 0.7482 0.6691 0.047 Uiso 1 1 calc R . . C15 C 0.7434(3) 0.68981(12) 0.63354(14) 0.0383(7) Uani 1 1 d . . . C16 C 0.7167(3) 0.71450(12) 0.57884(15) 0.0431(8) Uani 1 1 d . . . H16 H 0.7439 0.7471 0.5736 0.052 Uiso 1 1 calc R . . C17 C 0.6516(3) 0.69121(14) 0.53372(15) 0.0483(9) Uani 1 1 d . . . H17 H 0.6335 0.7083 0.4983 0.058 Uiso 1 1 calc R . . C18 C 0.6118(3) 0.64212(13) 0.53996(15) 0.0449(8) Uani 1 1 d . . . H18 H 0.5688 0.6262 0.5086 0.054 Uiso 1 1 calc R . . C19 C 0.6362(3) 0.61742(12) 0.59255(14) 0.0389(7) Uani 1 1 d . . . C20 C 0.7004(3) 0.64127(12) 0.64068(13) 0.0348(7) Uani 1 1 d . . . C21 C 0.6614(5) 0.42781(17) 0.8063(2) 0.0942(17) Uani 1 1 d . . . H21A H 0.7232 0.4037 0.8131 0.141 Uiso 1 1 calc R . . H21B H 0.6114 0.4181 0.7720 0.141 Uiso 1 1 calc R . . H21C H 0.6175 0.4288 0.8399 0.141 Uiso 1 1 calc R . . C22 C 0.5290(3) 0.54374(14) 0.56010(16) 0.0546(9) Uani 1 1 d . . . H22A H 0.4623 0.5644 0.5488 0.082 Uiso 1 1 calc R . . H22B H 0.5043 0.5121 0.5753 0.082 Uiso 1 1 calc R . . H22C H 0.5707 0.5377 0.5263 0.082 Uiso 1 1 calc R . . C23 C 0.4460(4) 0.5239(2) 0.7659(2) 0.0876(15) Uani 1 1 d . . . H23A H 0.4108 0.4932 0.7503 0.131 Uiso 1 1 calc R . . H23B H 0.3865 0.5468 0.7756 0.131 Uiso 1 1 calc R . . H23C H 0.4966 0.5164 0.8007 0.131 Uiso 1 1 calc R . . C24 C 0.6955(5) 0.43132(18) 0.6292(2) 0.0937(17) Uani 1 1 d . . . H24A H 0.6508 0.4275 0.5917 0.141 Uiso 1 1 calc R . . H24B H 0.7053 0.3990 0.6480 0.141 Uiso 1 1 calc R . . H24C H 0.7703 0.4452 0.6235 0.141 Uiso 1 1 calc R . . C25 C 0.3470(3) 0.63421(14) 0.63111(16) 0.0488(9) Uani 1 1 d . . . C26 C 0.2720(3) 0.59191(15) 0.61802(18) 0.0549(10) Uani 1 1 d . . . C27 C 0.2172(3) 0.58551(17) 0.56201(18) 0.0636(11) Uani 1 1 d . . . H27 H 0.1706 0.5573 0.5537 0.076 Uiso 1 1 calc R . . C28 C 0.2306(3) 0.62041(19) 0.51805(19) 0.0688(12) Uani 1 1 d . . . H28 H 0.1946 0.6150 0.4803 0.083 Uiso 1 1 calc R . . C29 C 0.2954(3) 0.66230(18) 0.52938(17) 0.0625(11) Uani 1 1 d . . . H29 H 0.3018 0.6859 0.4997 0.075 Uiso 1 1 calc R . . C30 C 0.3539(3) 0.67052(15) 0.58652(16) 0.0507(9) Uani 1 1 d . . . C31 C 0.4150(3) 0.71639(16) 0.59500(17) 0.0561(10) Uani 1 1 d . . . H31 H 0.4153 0.7378 0.5626 0.067 Uiso 1 1 calc R . . C32 C 0.5272(3) 0.77890(14) 0.64867(17) 0.0514(9) Uani 1 1 d . . . C33 C 0.5221(4) 0.81574(17) 0.6052(2) 0.0678(11) Uani 1 1 d . . . H33 H 0.4802 0.8099 0.5689 0.081 Uiso 1 1 calc R . . C34 C 0.5785(4) 0.86048(19) 0.6156(2) 0.0789(13) Uani 1 1 d . . . H34 H 0.5740 0.8850 0.5862 0.095 Uiso 1 1 calc R . . C35 C 0.6419(4) 0.86992(17) 0.6688(2) 0.0769(13) Uani 1 1 d . . . H35 H 0.6797 0.9007 0.6750 0.092 Uiso 1 1 calc R . . C36 C 0.6497(4) 0.83434(17) 0.7128(2) 0.0694(12) Uani 1 1 d . . . H36 H 0.6932 0.8407 0.7485 0.083 Uiso 1 1 calc R . . C37 C 0.5914(3) 0.78836(15) 0.70315(17) 0.0534(9) Uani 1 1 d . . . C38 C 0.6426(3) 0.75273(15) 0.79744(17) 0.0547(10) Uani 1 1 d . . . H38 H 0.6827 0.7826 0.8063 0.066 Uiso 1 1 calc R . . C39 C 0.6453(3) 0.71605(16) 0.84228(17) 0.0558(10) Uani 1 1 d . . . C40 C 0.7075(4) 0.72900(18) 0.89683(18) 0.0705(12) Uani 1 1 d . . . H40 H 0.7444 0.7602 0.9009 0.085 Uiso 1 1 calc R . . C41 C 0.7141(5) 0.6971(2) 0.9427(2) 0.0849(15) Uani 1 1 d . . . H41 H 0.7562 0.7061 0.9780 0.102 Uiso 1 1 calc R . . C42 C 0.6583(4) 0.6506(2) 0.9375(2) 0.0840(15) Uani 1 1 d . . . H42 H 0.6630 0.6288 0.9697 0.101 Uiso 1 1 calc R . . C43 C 0.5958(4) 0.63627(18) 0.88548(19) 0.0666(11) Uani 1 1 d . . . C44 C 0.5883(3) 0.66902(16) 0.83497(16) 0.0558(10) Uani 1 1 d . . . C45 C 0.1951(4) 0.51602(16) 0.6538(2) 0.0794(14) Uani 1 1 d . . . H45A H 0.1175 0.5245 0.6381 0.119 Uiso 1 1 calc R . . H45B H 0.1926 0.4979 0.6902 0.119 Uiso 1 1 calc R . . H45C H 0.2307 0.4953 0.6260 0.119 Uiso 1 1 calc R . . C46 C 0.5425(4) 0.5568(2) 0.9244(2) 0.0942(16) Uani 1 1 d . . . H46A H 0.6220 0.5493 0.9374 0.141 Uiso 1 1 calc R . . H46B H 0.5028 0.5263 0.9117 0.141 Uiso 1 1 calc R . . H46C H 0.5056 0.5714 0.9563 0.141 Uiso 1 1 calc R . . C47 C -0.0084(3) 0.64004(12) 0.60602(15) 0.0410(8) Uani 1 1 d . . . C48 C -0.0710(3) 0.61776(13) 0.55579(16) 0.0462(8) Uani 1 1 d . . . C49 C -0.0901(3) 0.64261(16) 0.50338(17) 0.0564(10) Uani 1 1 d . . . H49 H -0.1332 0.6274 0.4716 0.068 Uiso 1 1 calc R . . C50 C -0.0448(4) 0.69093(17) 0.4974(2) 0.0678(12) Uani 1 1 d . . . H50 H -0.0594 0.7082 0.4619 0.081 Uiso 1 1 calc R . . C51 C 0.0204(3) 0.71292(15) 0.54310(19) 0.0595(10) Uani 1 1 d . . . H51 H 0.0523 0.7447 0.5380 0.071 Uiso 1 1 calc R . . C52 C 0.0407(3) 0.68840(13) 0.59841(17) 0.0477(9) Uani 1 1 d . . . C53 C 0.1142(3) 0.71288(13) 0.64329(17) 0.0488(9) Uani 1 1 d . . . H53 H 0.1419 0.7447 0.6345 0.059 Uiso 1 1 calc R . . C54 C 0.2206(3) 0.72209(13) 0.73787(17) 0.0489(9) Uani 1 1 d . . . C55 C 0.2642(3) 0.77055(14) 0.7299(2) 0.0618(11) Uani 1 1 d . . . H55 H 0.2459 0.7876 0.6945 0.074 Uiso 1 1 calc R . . C56 C 0.3349(4) 0.79280(16) 0.7751(2) 0.0721(13) Uani 1 1 d . . . H56 H 0.3660 0.8246 0.7696 0.086 Uiso 1 1 calc R . . C57 C 0.3598(3) 0.76823(17) 0.8282(2) 0.0717(13) Uani 1 1 d . . . H57 H 0.4048 0.7842 0.8589 0.086 Uiso 1 1 calc R . . C58 C 0.3184(3) 0.72030(15) 0.83603(19) 0.0603(10) Uani 1 1 d . . . H58 H 0.3363 0.7037 0.8717 0.072 Uiso 1 1 calc R . . C59 C 0.2503(3) 0.69696(13) 0.79086(18) 0.0515(9) Uani 1 1 d . . . C60 C 0.2283(3) 0.61827(15) 0.83763(17) 0.0514(9) Uani 1 1 d . . . H60 H 0.2794 0.6307 0.8683 0.062 Uiso 1 1 calc R . . C61 C 0.1858(3) 0.56806(13) 0.84395(15) 0.0477(8) Uani 1 1 d . . . C62 C 0.2298(4) 0.53985(17) 0.89354(18) 0.0642(11) Uani 1 1 d . . . H62 H 0.2814 0.5551 0.9220 0.077 Uiso 1 1 calc R . . C63 C 0.1993(4) 0.49127(18) 0.90089(19) 0.0735(12) Uani 1 1 d . . . H63 H 0.2301 0.4734 0.9339 0.088 Uiso 1 1 calc R . . C64 C 0.1207(4) 0.46784(15) 0.85839(18) 0.0633(11) Uani 1 1 d . . . H64 H 0.1002 0.4343 0.8631 0.076 Uiso 1 1 calc R . . C65 C 0.0746(3) 0.49416(13) 0.81040(16) 0.0491(8) Uani 1 1 d . . . C66 C 0.1044(3) 0.54543(13) 0.80117(15) 0.0424(8) Uani 1 1 d . . . C67 C -0.1549(4) 0.54083(17) 0.51775(19) 0.0759(13) Uani 1 1 d . . . H67A H -0.2229 0.5570 0.4989 0.114 Uiso 1 1 calc R . . H67B H -0.1750 0.5079 0.5309 0.114 Uiso 1 1 calc R . . H67C H -0.0975 0.5379 0.4902 0.114 Uiso 1 1 calc R . . C68 C -0.0205(6) 0.42293(17) 0.7657(3) 0.127(3) Uani 1 1 d . . . H68A H 0.0526 0.4064 0.7626 0.190 Uiso 1 1 calc R . . H68B H -0.0736 0.4142 0.7321 0.190 Uiso 1 1 calc R . . H68C H -0.0518 0.4123 0.8011 0.190 Uiso 1 1 calc R . . C69 C 0.9076(5) 0.6576(2) 0.0753(3) 0.1017(18) Uani 1 1 d . . . H69A H 0.8330 0.6612 0.0900 0.153 Uiso 1 1 calc R . . H69B H 0.9120 0.6253 0.0564 0.153 Uiso 1 1 calc R . . H69C H 0.9178 0.6839 0.0473 0.153 Uiso 1 1 calc R . . Cl1 Cl 0.37970(9) 0.39132(4) 0.63038(4) 0.0590(3) Uani 1 1 d . . . Cl2 Cl 0.76752(9) 0.34151(4) 0.98263(5) 0.0639(3) Uani 1 1 d . . . Cu1 Cu 0.81138(3) 0.633489(14) 0.758676(17) 0.03823(12) Uani 1 1 d . . . Cu2 Cu 0.49667(4) 0.691151(17) 0.716066(19) 0.04842(14) Uani 1 1 d . . . Cu3 Cu 0.10225(3) 0.629761(14) 0.723342(18) 0.03995(12) Uani 1 1 d . . . H5C H 0.915(2) 0.5232(13) 0.7011(12) 0.044(10) Uiso 1 1 d D . . H5D H 0.877(3) 0.5456(13) 0.6523(15) 0.071(14) Uiso 1 1 d D . . H6M H 0.485(3) 0.5732(10) 0.7106(17) 0.064(13) Uiso 1 1 d D . . H7M H 0.5685(18) 0.4547(12) 0.6664(15) 0.040(10) Uiso 1 1 d D . . H24M H 1.058(5) 0.659(4) 0.105(5) 0.27(6) Uiso 1 1 d D . . Mn1 Mn 0.68506(4) 0.535625(18) 0.70475(2) 0.04105(14) Uani 1 1 d . . . N1 N 0.9039(2) 0.65185(10) 0.82937(11) 0.0379(6) Uani 1 1 d . . . N2 N 0.8489(2) 0.69933(9) 0.73036(12) 0.0374(6) Uani 1 1 d . . . N3 N 0.4714(2) 0.73153(11) 0.64445(13) 0.0492(7) Uani 1 1 d . . . N4 N 0.5893(2) 0.74865(12) 0.74494(13) 0.0505(7) Uani 1 1 d . . . N5 N 0.1462(2) 0.69525(10) 0.69509(13) 0.0442(7) Uani 1 1 d . . . N6 N 0.2024(2) 0.64788(11) 0.79366(13) 0.0442(7) Uani 1 1 d . . . O1 O 0.77263(19) 0.56806(8) 0.78388(9) 0.0433(5) Uani 1 1 d . . . O2 O 0.71622(19) 0.61502(8) 0.69041(9) 0.0424(5) Uani 1 1 d . . . O3 O 0.7089(2) 0.47643(9) 0.79708(11) 0.0581(7) Uani 1 1 d . . . O4 O 0.6032(2) 0.56912(8) 0.60469(10) 0.0470(6) Uani 1 1 d . . . O5 O 0.8581(2) 0.52294(10) 0.67608(12) 0.0496(6) Uani 1 1 d D . . O6 O 0.5105(2) 0.54603(12) 0.72329(14) 0.0653(8) Uani 1 1 d D . . O7 O 0.6371(2) 0.46393(10) 0.66495(12) 0.0601(7) Uani 1 1 d D . . O8 O 0.4023(2) 0.63663(9) 0.68419(11) 0.0529(6) Uani 1 1 d . . . O9 O 0.5302(2) 0.65327(10) 0.78689(11) 0.0589(7) Uani 1 1 d . . . O10 O 0.2610(2) 0.56102(11) 0.66445(13) 0.0685(8) Uani 1 1 d . . . O11 O 0.5379(3) 0.59143(13) 0.87656(13) 0.0806(9) Uani 1 1 d . . . O12 O 0.00085(19) 0.61447(8) 0.65510(10) 0.0439(5) Uani 1 1 d . . . O13 O 0.05371(19) 0.56806(8) 0.75459(10) 0.0451(6) Uani 1 1 d . . . O14 O -0.1098(2) 0.56980(9) 0.56647(11) 0.0560(6) Uani 1 1 d . . . O15 O -0.0040(3) 0.47516(9) 0.76716(12) 0.0635(7) Uani 1 1 d . . . O16 O 0.4437(3) 0.40733(17) 0.68290(13) 0.1193(15) Uani 1 1 d . . . O17 O 0.3854(3) 0.42915(11) 0.58734(14) 0.0884(10) Uani 1 1 d . . . O18 O 0.4323(4) 0.34711(13) 0.61125(19) 0.1193(14) Uani 1 1 d . . . O19 O 0.2645(3) 0.38072(16) 0.63984(19) 0.1149(14) Uani 1 1 d . . . O20 O 0.7741(3) 0.33096(16) 0.92195(15) 0.1027(12) Uani 1 1 d . . . O21 O 0.8753(3) 0.35963(17) 1.00853(18) 0.1190(14) Uani 1 1 d . . . O22 O 0.6815(3) 0.37843(16) 0.9862(2) 0.1239(15) Uani 1 1 d . . . O23 O 0.7373(4) 0.29744(16) 1.01058(19) 0.1420(18) Uani 1 1 d . . . O24 O 0.9940(6) 0.66099(18) 0.1216(2) 0.1199(14) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0403(17) 0.0390(17) 0.0365(18) 0.0024(14) 0.0025(14) 0.0041(14) C2 0.050(2) 0.049(2) 0.043(2) 0.0056(16) 0.0002(16) -0.0012(16) C3 0.069(3) 0.049(2) 0.059(3) 0.0179(19) 0.000(2) -0.0005(19) C4 0.075(3) 0.069(3) 0.038(2) 0.0139(19) -0.0139(19) 0.005(2) C5 0.062(2) 0.059(2) 0.037(2) 0.0039(17) -0.0104(17) 0.0059(18) C6 0.0450(18) 0.0436(19) 0.0352(18) -0.0026(14) 0.0007(14) 0.0048(15) C7 0.0440(19) 0.046(2) 0.038(2) -0.0111(15) -0.0012(15) 0.0030(15) C8 0.0416(18) 0.0362(17) 0.046(2) -0.0128(15) 0.0094(15) -0.0006(14) C9 0.046(2) 0.059(2) 0.044(2) -0.0146(17) 0.0018(16) -0.0064(17) C10 0.057(2) 0.055(2) 0.060(3) -0.025(2) 0.0049(19) -0.0123(18) C11 0.069(3) 0.041(2) 0.075(3) -0.018(2) 0.013(2) -0.0127(18) C12 0.058(2) 0.040(2) 0.056(2) -0.0033(17) 0.0081(18) -0.0052(16) C13 0.0395(17) 0.0367(17) 0.045(2) -0.0090(15) 0.0060(15) 0.0010(14) C14 0.0401(17) 0.0337(17) 0.045(2) 0.0007(14) 0.0100(15) 0.0047(13) C15 0.0380(17) 0.0405(18) 0.0371(18) 0.0013(14) 0.0073(14) 0.0047(14) C16 0.0487(19) 0.0392(18) 0.042(2) 0.0103(15) 0.0078(15) 0.0047(15) C17 0.053(2) 0.058(2) 0.0343(19) 0.0094(16) 0.0050(16) 0.0061(17) C18 0.0446(19) 0.058(2) 0.0311(18) -0.0003(15) 0.0010(14) 0.0020(16) C19 0.0398(17) 0.0424(18) 0.0352(18) 0.0011(14) 0.0074(14) 0.0044(14) C20 0.0340(16) 0.0392(17) 0.0310(17) 0.0012(13) 0.0021(13) 0.0026(13) C21 0.126(4) 0.062(3) 0.087(4) 0.015(2) -0.029(3) -0.042(3) C22 0.053(2) 0.060(2) 0.048(2) -0.0079(18) -0.0074(17) -0.0119(18) C23 0.084(3) 0.109(4) 0.073(3) 0.007(3) 0.020(3) -0.005(3) C24 0.100(4) 0.071(3) 0.113(4) -0.042(3) 0.024(3) -0.011(3) C25 0.0349(18) 0.067(2) 0.044(2) -0.0181(18) 0.0032(15) 0.0090(16) C26 0.041(2) 0.066(3) 0.057(2) -0.019(2) 0.0059(17) 0.0056(17) C27 0.046(2) 0.082(3) 0.061(3) -0.031(2) -0.0038(19) 0.008(2) C28 0.054(2) 0.102(4) 0.049(3) -0.026(2) -0.0048(19) 0.016(2) C29 0.053(2) 0.088(3) 0.045(2) -0.011(2) -0.0029(18) 0.009(2) C30 0.0387(19) 0.067(2) 0.047(2) -0.0113(18) 0.0056(16) 0.0085(17) C31 0.046(2) 0.074(3) 0.048(2) -0.0023(19) 0.0055(17) 0.0109(19) C32 0.0411(19) 0.058(2) 0.055(2) -0.0096(18) 0.0047(17) 0.0110(17) C33 0.065(3) 0.071(3) 0.068(3) 0.003(2) 0.006(2) 0.012(2) C34 0.081(3) 0.075(3) 0.083(4) 0.006(3) 0.019(3) 0.007(3) C35 0.078(3) 0.057(3) 0.099(4) -0.014(3) 0.029(3) -0.006(2) C36 0.067(3) 0.070(3) 0.073(3) -0.019(2) 0.014(2) -0.005(2) C37 0.050(2) 0.057(2) 0.054(2) -0.0116(19) 0.0124(18) 0.0095(17) C38 0.046(2) 0.058(2) 0.060(3) -0.0221(19) 0.0014(18) 0.0097(17) C39 0.050(2) 0.068(3) 0.047(2) -0.0200(19) -0.0046(17) 0.0163(19) C40 0.074(3) 0.083(3) 0.051(3) -0.021(2) -0.013(2) 0.023(2) C41 0.100(4) 0.093(4) 0.056(3) -0.034(3) -0.023(3) 0.027(3) C42 0.091(4) 0.110(4) 0.048(3) -0.010(3) -0.005(2) 0.037(3) C43 0.062(3) 0.082(3) 0.055(3) -0.014(2) 0.002(2) 0.015(2) C44 0.050(2) 0.075(3) 0.042(2) -0.0116(19) 0.0000(17) 0.0203(19) C45 0.079(3) 0.060(3) 0.100(4) -0.025(3) 0.009(3) -0.006(2) C46 0.087(4) 0.117(4) 0.080(4) 0.025(3) 0.013(3) 0.007(3) C47 0.0349(17) 0.0439(19) 0.045(2) 0.0050(15) 0.0093(15) 0.0082(14) C48 0.0381(18) 0.054(2) 0.047(2) 0.0034(17) 0.0065(15) 0.0039(16) C49 0.047(2) 0.077(3) 0.046(2) 0.0087(19) 0.0056(17) 0.0084(19) C50 0.058(2) 0.086(3) 0.061(3) 0.034(2) 0.014(2) 0.013(2) C51 0.055(2) 0.057(2) 0.069(3) 0.023(2) 0.015(2) 0.0054(19) C52 0.0408(19) 0.049(2) 0.055(2) 0.0095(17) 0.0133(16) 0.0072(15) C53 0.0462(19) 0.0376(18) 0.064(3) 0.0034(17) 0.0130(18) -0.0002(15) C54 0.0395(18) 0.044(2) 0.065(3) -0.0169(18) 0.0171(17) -0.0023(15) C55 0.057(2) 0.050(2) 0.081(3) -0.010(2) 0.020(2) -0.0071(18) C56 0.058(3) 0.050(2) 0.110(4) -0.023(3) 0.024(3) -0.019(2) C57 0.047(2) 0.071(3) 0.098(4) -0.040(3) 0.013(2) -0.014(2) C58 0.046(2) 0.064(3) 0.072(3) -0.022(2) 0.0064(19) -0.0086(18) C59 0.0412(19) 0.046(2) 0.069(3) -0.0191(19) 0.0156(18) -0.0057(16) C60 0.0418(19) 0.063(2) 0.049(2) -0.0194(19) 0.0003(16) -0.0065(17) C61 0.049(2) 0.054(2) 0.039(2) -0.0043(16) 0.0028(16) 0.0016(16) C62 0.068(3) 0.075(3) 0.048(2) -0.005(2) -0.006(2) 0.000(2) C63 0.091(3) 0.075(3) 0.052(3) 0.014(2) -0.005(2) 0.013(3) C64 0.082(3) 0.051(2) 0.056(3) 0.0062(19) 0.000(2) 0.005(2) C65 0.050(2) 0.045(2) 0.051(2) -0.0010(17) -0.0002(17) 0.0039(16) C66 0.0446(19) 0.0445(19) 0.0385(19) -0.0067(15) 0.0062(15) 0.0032(15) C67 0.086(3) 0.078(3) 0.061(3) -0.022(2) -0.007(2) -0.007(2) C68 0.176(6) 0.041(3) 0.145(5) -0.002(3) -0.074(5) -0.009(3) C69 0.105(4) 0.089(4) 0.110(5) 0.026(3) 0.009(4) 0.002(3) Cl1 0.0707(6) 0.0490(5) 0.0541(6) 0.0066(4) -0.0110(5) -0.0112(4) Cl2 0.0717(7) 0.0580(6) 0.0587(6) -0.0053(5) -0.0102(5) -0.0015(5) Cu1 0.0460(2) 0.0346(2) 0.0328(2) -0.00047(16) -0.00250(17) -0.00410(16) Cu2 0.0447(2) 0.0579(3) 0.0418(3) -0.0125(2) -0.00016(19) 0.00571(19) Cu3 0.0424(2) 0.0360(2) 0.0416(2) -0.00509(17) 0.00526(18) -0.00286(16) Mn1 0.0448(3) 0.0386(3) 0.0386(3) -0.0014(2) -0.0016(2) -0.0075(2) N1 0.0414(15) 0.0362(14) 0.0354(15) -0.0048(12) 0.0006(12) -0.0009(12) N2 0.0386(14) 0.0354(14) 0.0383(16) -0.0035(12) 0.0050(12) -0.0002(11) N3 0.0455(16) 0.0583(19) 0.0435(18) -0.0062(14) 0.0023(13) 0.0084(14) N4 0.0460(16) 0.0596(19) 0.0453(18) -0.0181(15) 0.0017(14) 0.0090(14) N5 0.0425(15) 0.0372(15) 0.0545(19) -0.0057(13) 0.0134(14) -0.0018(12) N6 0.0407(16) 0.0426(16) 0.0497(18) -0.0130(14) 0.0067(13) -0.0037(12) O1 0.0543(14) 0.0419(13) 0.0318(12) 0.0055(10) -0.0061(10) -0.0082(10) O2 0.0518(13) 0.0402(12) 0.0333(12) 0.0043(10) -0.0061(10) -0.0082(10) O3 0.0757(17) 0.0424(14) 0.0528(16) 0.0091(11) -0.0111(13) -0.0185(12) O4 0.0552(14) 0.0463(14) 0.0380(13) -0.0002(10) -0.0034(11) -0.0114(11) O5 0.0452(15) 0.0513(15) 0.0512(16) 0.0028(13) -0.0016(13) -0.0035(12) O6 0.0526(16) 0.0642(19) 0.081(2) 0.0166(16) 0.0184(14) 0.0057(14) O7 0.0643(18) 0.0526(16) 0.0637(18) -0.0134(13) 0.0074(14) -0.0182(14) O8 0.0508(15) 0.0608(16) 0.0458(15) -0.0116(12) -0.0023(12) 0.0017(11) O9 0.0635(16) 0.0677(17) 0.0429(15) -0.0085(13) -0.0086(12) 0.0045(13) O10 0.0637(17) 0.0660(18) 0.074(2) -0.0137(15) -0.0012(15) -0.0066(14) O11 0.087(2) 0.092(2) 0.0604(19) 0.0095(17) -0.0053(16) 0.0006(18) O12 0.0513(13) 0.0390(12) 0.0408(13) 0.0013(10) 0.0004(10) -0.0047(10) O13 0.0532(14) 0.0407(13) 0.0399(14) 0.0014(10) -0.0025(11) -0.0072(10) O14 0.0630(16) 0.0559(16) 0.0473(15) -0.0026(12) -0.0046(12) -0.0033(12) O15 0.0812(19) 0.0394(14) 0.0652(18) 0.0010(12) -0.0173(15) -0.0067(13) O16 0.126(3) 0.184(4) 0.0437(18) -0.003(2) -0.0122(19) -0.081(3) O17 0.134(3) 0.0606(19) 0.072(2) 0.0219(15) 0.019(2) 0.0076(18) O18 0.150(4) 0.065(2) 0.139(4) 0.002(2) -0.008(3) 0.028(2) O19 0.071(2) 0.142(4) 0.129(3) 0.029(3) -0.005(2) -0.030(2) O20 0.104(3) 0.140(3) 0.062(2) -0.021(2) -0.0071(18) 0.008(2) O21 0.087(3) 0.153(4) 0.110(3) -0.018(3) -0.028(2) -0.028(2) O22 0.105(3) 0.122(3) 0.140(4) -0.056(3) -0.013(3) 0.032(2) O23 0.205(5) 0.107(3) 0.111(3) 0.034(3) -0.001(3) -0.049(3) O24 0.156(4) 0.115(3) 0.089(3) 0.019(2) 0.014(3) -0.019(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.318(4) . ? C1 C6 1.403(5) . ? C1 C2 1.414(5) . ? C2 C3 1.369(5) . ? C2 O3 1.386(4) . ? C3 C4 1.391(5) . ? C3 H3 0.9300 . ? C4 C5 1.343(5) . ? C4 H4 0.9300 . ? C5 C6 1.416(5) . ? C5 H5A 0.9300 . ? C6 C7 1.440(5) . ? C7 N1 1.289(4) . ? C7 H7 0.9300 . ? C8 C9 1.388(5) . ? C8 C13 1.405(5) . ? C8 N1 1.417(4) . ? C9 C10 1.364(5) . ? C9 H9 0.9300 . ? C10 C11 1.375(6) . ? C10 H10 0.9300 . ? C11 C12 1.374(5) . ? C11 H11 0.9300 . ? C12 C13 1.386(5) . ? C12 H12 0.9300 . ? C13 N2 1.420(4) . ? C14 N2 1.288(4) . ? C14 C15 1.433(5) . ? C14 H14 0.9300 . ? C15 C20 1.395(4) . ? C15 C16 1.414(4) . ? C16 C17 1.361(5) . ? C16 H16 0.9300 . ? C17 C18 1.392(5) . ? C17 H17 0.9300 . ? C18 C19 1.370(5) . ? C18 H18 0.9300 . ? C19 O4 1.371(4) . ? C19 C20 1.412(4) . ? C20 O2 1.327(4) . ? C21 O3 1.424(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O4 1.432(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O6 1.408(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O7 1.405(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O8 1.313(4) . ? C25 C30 1.407(5) . ? C25 C26 1.431(5) . ? C26 O10 1.353(5) . ? C26 C27 1.378(5) . ? C27 C28 1.383(6) . ? C27 H27 0.9300 . ? C28 C29 1.350(6) . ? C28 H28 0.9300 . ? C29 C30 1.424(5) . ? C29 H29 0.9300 . ? C30 C31 1.410(5) . ? C31 N3 1.308(5) . ? C31 H31 0.9300 . ? C32 C33 1.387(6) . ? C32 C37 1.405(5) . ? C32 N3 1.410(5) . ? C33 C34 1.362(6) . ? C33 H33 0.9300 . ? C34 C35 1.377(7) . ? C34 H34 0.9300 . ? C35 C36 1.372(6) . ? C35 H35 0.9300 . ? C36 C37 1.399(6) . ? C36 H36 0.9300 . ? C37 N4 1.421(5) . ? C38 N4 1.295(5) . ? C38 C39 1.408(6) . ? C38 H38 0.9300 . ? C39 C44 1.412(6) . ? C39 C40 1.416(5) . ? C40 C41 1.340(7) . ? C40 H40 0.9300 . ? C41 C42 1.390(7) . ? C41 H41 0.9300 . ? C42 C43 1.380(6) . ? C42 H42 0.9300 . ? C43 O11 1.370(5) . ? C43 C44 1.437(6) . ? C44 O9 1.296(4) . ? C45 O10 1.423(5) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 O11 1.421(5) . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 O12 1.303(4) . ? C47 C52 1.419(5) . ? C47 C48 1.421(5) . ? C48 C49 1.362(5) . ? C48 O14 1.377(4) . ? C49 C50 1.395(6) . ? C49 H49 0.9300 . ? C50 C51 1.356(6) . ? C50 H50 0.9300 . ? C51 C52 1.416(5) . ? C51 H51 0.9300 . ? C52 C53 1.421(5) . ? C53 N5 1.289(4) . ? C53 H53 0.9300 . ? C54 C59 1.392(5) . ? C54 C55 1.398(5) . ? C54 N5 1.425(4) . ? C55 C56 1.382(6) . ? C55 H55 0.9300 . ? C56 C57 1.380(7) . ? C56 H56 0.9300 . ? C57 C58 1.375(6) . ? C57 H57 0.9300 . ? C58 C59 1.380(5) . ? C58 H58 0.9300 . ? C59 N6 1.417(4) . ? C60 N6 1.284(5) . ? C60 C61 1.430(5) . ? C60 H60 0.9300 . ? C61 C62 1.407(5) . ? C61 C66 1.420(5) . ? C62 C63 1.350(6) . ? C62 H62 0.9300 . ? C63 C64 1.406(6) . ? C63 H63 0.9300 . ? C64 C65 1.361(5) . ? C64 H64 0.9300 . ? C65 O15 1.369(4) . ? C65 C66 1.422(5) . ? C66 O13 1.307(4) . ? C67 O14 1.407(4) . ? C67 H67A 0.9600 . ? C67 H67B 0.9600 . ? C67 H67C 0.9600 . ? C68 O15 1.397(5) . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? C69 O24 1.384(7) . ? C69 H69A 0.9600 . ? C69 H69B 0.9600 . ? C69 H69C 0.9600 . ? Cl1 O19 1.398(4) . ? Cl1 O17 1.408(3) . ? Cl1 O18 1.408(4) . ? Cl1 O16 1.409(3) . ? Cl2 O23 1.391(4) . ? Cl2 O22 1.404(4) . ? Cl2 O21 1.411(4) . ? Cl2 O20 1.419(3) . ? Cu1 O2 1.880(2) . ? Cu1 O1 1.894(2) . ? Cu1 N1 1.907(3) . ? Cu1 N2 1.924(3) . ? Cu2 O9 1.907(3) . ? Cu2 O8 1.911(2) . ? Cu2 N4 1.940(3) . ? Cu2 N3 1.949(3) . ? Cu3 O13 1.890(2) . ? Cu3 O12 1.897(2) . ? Cu3 N5 1.936(3) . ? Cu3 N6 1.943(3) . ? Mn1 O6 2.120(3) . ? Mn1 O7 2.154(3) . ? Mn1 O1 2.158(2) . ? Mn1 O2 2.165(2) . ? Mn1 O5 2.190(3) . ? Mn1 O4 2.541(2) . ? Mn1 O3 2.616(2) . ? O5 H5C 0.827(18) . ? O5 H5D 0.853(19) . ? O6 H6M 0.821(18) . ? O7 H7M 0.834(18) . ? O24 H24M 0.855(15) . ? 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 C6 124.5(3) . . ? O1 C1 C2 117.1(3) . . ? C6 C1 C2 118.4(3) . . ? C3 C2 O3 125.7(3) . . ? C3 C2 C1 121.1(3) . . ? O3 C2 C1 113.3(3) . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C5 118.8(3) . . ? C1 C6 C7 123.8(3) . . ? C5 C6 C7 117.4(3) . . ? N1 C7 C6 125.9(3) . . ? N1 C7 H7 117.0 . . ? C6 C7 H7 117.1 . . ? C9 C8 C13 119.7(3) . . ? C9 C8 N1 125.7(3) . . ? C13 C8 N1 114.6(3) . . ? C10 C9 C8 120.0(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.3(4) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.9(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.7(4) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 119.3(3) . . ? C12 C13 N2 125.3(3) . . ? C8 C13 N2 115.5(3) . . ? N2 C14 C15 126.1(3) . . ? N2 C14 H14 116.9 . . ? C15 C14 H14 116.9 . . ? C20 C15 C16 118.6(3) . . ? C20 C15 C14 123.7(3) . . ? C16 C15 C14 117.7(3) . . ? C17 C16 C15 120.8(3) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.7(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 119.6(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 O4 125.8(3) . . ? C18 C19 C20 120.8(3) . . ? O4 C19 C20 113.4(3) . . ? O2 C20 C15 124.2(3) . . ? O2 C20 C19 116.5(3) . . ? C15 C20 C19 119.3(3) . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O6 C23 H23A 109.5 . . ? O6 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O6 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O7 C24 H24A 109.5 . . ? O7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 C30 125.1(3) . . ? O8 C25 C26 117.4(4) . . ? C30 C25 C26 117.5(3) . . ? O10 C26 C27 125.4(4) . . ? O10 C26 C25 114.4(3) . . ? C27 C26 C25 120.2(4) . . ? C26 C27 C28 120.9(4) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C29 C28 C27 120.7(4) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 120.4(4) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C25 C30 C31 123.6(3) . . ? C25 C30 C29 120.0(4) . . ? C31 C30 C29 116.4(4) . . ? N3 C31 C30 125.7(4) . . ? N3 C31 H31 117.1 . . ? C30 C31 H31 117.1 . . ? C33 C32 C37 119.1(4) . . ? C33 C32 N3 126.2(4) . . ? C37 C32 N3 114.7(3) . . ? C34 C33 C32 120.2(5) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 121.0(5) . . ? C33 C34 H34 119.5 . . ? C35 C34 H34 119.5 . . ? C36 C35 C34 120.6(4) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C37 119.2(4) . . ? C35 C36 H36 120.4 . . ? C37 C36 H36 120.4 . . ? C36 C37 C32 119.9(4) . . ? C36 C37 N4 125.4(4) . . ? C32 C37 N4 114.7(3) . . ? N4 C38 C39 125.9(4) . . ? N4 C38 H38 117.0 . . ? C39 C38 H38 117.0 . . ? C38 C39 C44 123.1(3) . . ? C38 C39 C40 116.2(4) . . ? C44 C39 C40 120.6(4) . . ? C41 C40 C39 121.1(5) . . ? C41 C40 H40 119.5 . . ? C39 C40 H40 119.5 . . ? C40 C41 C42 120.2(4) . . ? C40 C41 H41 119.9 . . ? C42 C41 H41 119.9 . . ? C43 C42 C41 121.1(5) . . ? C43 C42 H42 119.5 . . ? C41 C42 H42 119.5 . . ? O11 C43 C42 125.0(5) . . ? O11 C43 C44 114.5(4) . . ? C42 C43 C44 120.5(5) . . ? O9 C44 C39 125.5(4) . . ? O9 C44 C43 117.9(4) . . ? C39 C44 C43 116.6(4) . . ? O10 C45 H45A 109.5 . . ? O10 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? O10 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O11 C46 H46A 109.5 . . ? O11 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O11 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O12 C47 C52 125.0(3) . . ? O12 C47 C48 117.8(3) . . ? C52 C47 C48 117.1(3) . . ? C49 C48 O14 125.0(3) . . ? C49 C48 C47 122.0(3) . . ? O14 C48 C47 113.0(3) . . ? C48 C49 C50 120.0(4) . . ? C48 C49 H49 120.0 . . ? C50 C49 H49 120.0 . . ? C51 C50 C49 120.4(4) . . ? C51 C50 H50 119.8 . . ? C49 C50 H50 119.8 . . ? C50 C51 C52 121.1(4) . . ? C50 C51 H51 119.4 . . ? C52 C51 H51 119.4 . . ? C51 C52 C47 119.3(4) . . ? C51 C52 C53 117.8(3) . . ? C47 C52 C53 122.9(3) . . ? N5 C53 C52 126.2(3) . . ? N5 C53 H53 116.9 . . ? C52 C53 H53 116.9 . . ? C59 C54 C55 119.4(4) . . ? C59 C54 N5 115.8(3) . . ? C55 C54 N5 124.8(4) . . ? C56 C55 C54 119.3(4) . . ? C56 C55 H55 120.3 . . ? C54 C55 H55 120.3 . . ? C57 C56 C55 120.6(4) . . ? C57 C56 H56 119.7 . . ? C55 C56 H56 119.7 . . ? C58 C57 C56 120.2(4) . . ? C58 C57 H57 119.9 . . ? C56 C57 H57 119.9 . . ? C57 C58 C59 119.9(4) . . ? C57 C58 H58 120.1 . . ? C59 C58 H58 120.1 . . ? C58 C59 C54 120.4(4) . . ? C58 C59 N6 125.1(4) . . ? C54 C59 N6 114.4(3) . . ? N6 C60 C61 126.2(3) . . ? N6 C60 H60 116.9 . . ? C61 C60 H60 116.9 . . ? C62 C61 C66 119.3(3) . . ? C62 C61 C60 118.3(3) . . ? C66 C61 C60 122.3(3) . . ? C63 C62 C61 121.8(4) . . ? C63 C62 H62 119.1 . . ? C61 C62 H62 119.1 . . ? C62 C63 C64 119.7(4) . . ? C62 C63 H63 120.2 . . ? C64 C63 H63 120.2 . . ? C65 C64 C63 120.2(4) . . ? C65 C64 H64 119.9 . . ? C63 C64 H64 119.9 . . ? C64 C65 O15 124.7(3) . . ? C64 C65 C66 121.8(3) . . ? O15 C65 C66 113.5(3) . . ? O13 C66 C61 125.3(3) . . ? O13 C66 C65 117.5(3) . . ? C61 C66 C65 117.1(3) . . ? O14 C67 H67A 109.5 . . ? O14 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? O14 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? O15 C68 H68A 109.5 . . ? O15 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? O15 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? O24 C69 H69A 109.5 . . ? O24 C69 H69B 109.5 . . ? H69A C69 H69B 109.5 . . ? O24 C69 H69C 109.5 . . ? H69A C69 H69C 109.5 . . ? H69B C69 H69C 109.5 . . ? O19 Cl1 O17 111.1(2) . . ? O19 Cl1 O18 109.1(3) . . ? O17 Cl1 O18 109.0(2) . . ? O19 Cl1 O16 111.0(2) . . ? O17 Cl1 O16 108.7(2) . . ? O18 Cl1 O16 107.8(3) . . ? O23 Cl2 O22 110.4(3) . . ? O23 Cl2 O21 110.2(3) . . ? O22 Cl2 O21 110.0(3) . . ? O23 Cl2 O20 108.7(3) . . ? O22 Cl2 O20 107.4(2) . . ? O21 Cl2 O20 110.2(2) . . ? O2 Cu1 O1 82.85(9) . . ? O2 Cu1 N1 178.19(11) . . ? O1 Cu1 N1 96.18(10) . . ? O2 Cu1 N2 95.29(10) . . ? O1 Cu1 N2 178.05(10) . . ? N1 Cu1 N2 85.70(11) . . ? O9 Cu2 O8 89.13(12) . . ? O9 Cu2 N4 93.83(12) . . ? O8 Cu2 N4 176.99(12) . . ? O9 Cu2 N3 176.67(12) . . ? O8 Cu2 N3 93.66(12) . . ? N4 Cu2 N3 83.40(13) . . ? O13 Cu3 O12 86.62(9) . . ? O13 Cu3 N5 176.20(10) . . ? O12 Cu3 N5 94.64(11) . . ? O13 Cu3 N6 94.51(11) . . ? O12 Cu3 N6 177.68(11) . . ? N5 Cu3 N6 84.11(13) . . ? O6 Mn1 O7 89.27(12) . . ? O6 Mn1 O1 99.23(11) . . ? O7 Mn1 O1 141.57(10) . . ? O6 Mn1 O2 94.55(10) . . ? O7 Mn1 O2 146.47(10) . . ? O1 Mn1 O2 70.57(8) . . ? O6 Mn1 O5 173.97(12) . . ? O7 Mn1 O5 86.83(10) . . ? O1 Mn1 O5 86.67(10) . . ? O2 Mn1 O5 86.21(9) . . ? O6 Mn1 O4 81.63(10) . . ? O7 Mn1 O4 82.68(9) . . ? O1 Mn1 O4 135.51(8) . . ? O2 Mn1 O4 65.05(7) . . ? O5 Mn1 O4 93.31(9) . . ? O6 Mn1 O3 86.90(10) . . ? O7 Mn1 O3 79.16(9) . . ? O1 Mn1 O3 64.12(8) . . ? O2 Mn1 O3 134.26(8) . . ? O5 Mn1 O3 96.86(10) . . ? O4 Mn1 O3 158.61(8) . . ? C7 N1 C8 123.1(3) . . ? C7 N1 Cu1 124.2(2) . . ? C8 N1 Cu1 112.7(2) . . ? C14 N2 C13 124.2(3) . . ? C14 N2 Cu1 124.2(2) . . ? C13 N2 Cu1 111.5(2) . . ? C31 N3 C32 121.2(3) . . ? C31 N3 Cu2 125.0(3) . . ? C32 N3 Cu2 113.7(2) . . ? C38 N4 C37 121.2(3) . . ? C38 N4 Cu2 125.2(3) . . ? C37 N4 Cu2 113.6(2) . . ? C53 N5 C54 123.0(3) . . ? C53 N5 Cu3 124.6(2) . . ? C54 N5 Cu3 112.4(2) . . ? C60 N6 C59 122.3(3) . . ? C60 N6 Cu3 124.5(2) . . ? C59 N6 Cu3 113.2(3) . . ? C1 O1 Cu1 125.4(2) . . ? C1 O1 Mn1 131.5(2) . . ? Cu1 O1 Mn1 102.55(9) . . ? C20 O2 Cu1 126.2(2) . . ? C20 O2 Mn1 128.85(19) . . ? Cu1 O2 Mn1 102.77(10) . . ? C2 O3 C21 115.9(3) . . ? C2 O3 Mn1 113.58(19) . . ? C21 O3 Mn1 130.4(2) . . ? C19 O4 C22 117.1(3) . . ? C19 O4 Mn1 114.83(18) . . ? C22 O4 Mn1 128.1(2) . . ? Mn1 O5 H5C 119(2) . . ? Mn1 O5 H5D 112(3) . . ? H5C O5 H5D 101(4) . . ? C23 O6 Mn1 131.4(3) . . ? C23 O6 H6M 114(3) . . ? Mn1 O6 H6M 111(3) . . ? C24 O7 Mn1 131.9(3) . . ? C24 O7 H7M 111(2) . . ? Mn1 O7 H7M 117(2) . . ? C25 O8 Cu2 126.6(2) . . ? C44 O9 Cu2 126.2(3) . . ? C26 O10 C45 117.6(3) . . ? C43 O11 C46 117.7(4) . . ? C47 O12 Cu3 125.7(2) . . ? C66 O13 Cu3 125.2(2) . . ? C48 O14 C67 117.8(3) . . ? C65 O15 C68 117.5(3) . . ? C69 O24 H24M 105(8) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.433 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 930930' ####################################################################### # # 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_global # Attachment '4.cif' data_4 #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C69 H68 Cl2 Cu3 Fe N6 O24' _chemical_formula_weight 1682.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.557(2) _cell_length_b 26.632(5) _cell_length_c 22.822(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.719(6) _cell_angle_gamma 90.00 _cell_volume 6989(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9995 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.44 _exptl_crystal_description rectangular _exptl_crystal_colour brown _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3452 _exptl_absorpt_coefficient_mu 1.266 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7182 _exptl_absorpt_correction_T_max 0.7681 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 79054 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.58 _reflns_number_total 12973 _reflns_number_gt 10032 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8058P] 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 12973 _refine_ls_number_parameters 975 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.002 _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 0.8058(2) 0.54699(11) 0.83474(13) 0.0370(6) Uani 1 1 d . . . C2 C 0.7724(3) 0.49665(12) 0.84427(14) 0.0446(7) Uani 1 1 d . . . C3 C 0.8029(3) 0.47365(13) 0.89733(16) 0.0564(9) Uani 1 1 d . . . H3 H 0.7791 0.4408 0.9033 0.068 Uiso 1 1 calc R . . C4 C 0.8683(3) 0.49874(14) 0.94200(15) 0.0602(9) Uani 1 1 d . . . H4 H 0.8882 0.4827 0.9778 0.072 Uiso 1 1 calc R . . C5 C 0.9041(3) 0.54686(13) 0.93416(14) 0.0514(8) Uani 1 1 d . . . H5 H 0.9484 0.5632 0.9646 0.062 Uiso 1 1 calc R . . C6 C 0.8746(3) 0.57215(11) 0.88024(13) 0.0401(7) Uani 1 1 d . . . C7 C 0.9190(3) 0.62248(11) 0.87525(13) 0.0411(7) Uani 1 1 d . . . H7 H 0.9638 0.6355 0.9079 0.049 Uiso 1 1 calc R . . C8 C 0.9482(2) 0.70040(11) 0.82660(14) 0.0393(7) Uani 1 1 d . . . C9 C 1.0194(3) 0.72375(12) 0.87105(15) 0.0488(8) Uani 1 1 d . . . H9 H 1.0408 0.7068 0.9061 0.059 Uiso 1 1 calc R . . C10 C 1.0586(3) 0.77190(13) 0.86351(17) 0.0555(9) Uani 1 1 d . . . H10 H 1.1059 0.7875 0.8935 0.067 Uiso 1 1 calc R . . C11 C 1.0277(3) 0.79708(13) 0.81132(18) 0.0576(9) Uani 1 1 d . . . H11 H 1.0545 0.8296 0.8067 0.069 Uiso 1 1 calc R . . C12 C 0.9582(3) 0.77510(11) 0.76630(16) 0.0505(8) Uani 1 1 d . . . H12 H 0.9377 0.7926 0.7315 0.061 Uiso 1 1 calc R . . C13 C 0.9186(2) 0.72601(10) 0.77330(13) 0.0387(7) Uani 1 1 d . . . C14 C 0.8135(2) 0.71522(10) 0.67803(13) 0.0377(7) Uani 1 1 d . . . H14 H 0.8377 0.7473 0.6689 0.045 Uiso 1 1 calc R . . C15 C 0.7426(2) 0.68902(10) 0.63309(13) 0.0342(6) Uani 1 1 d . . . C16 C 0.7154(3) 0.71319(11) 0.57829(14) 0.0420(7) Uani 1 1 d . . . H16 H 0.7421 0.7457 0.5732 0.050 Uiso 1 1 calc R . . C17 C 0.6513(3) 0.69019(12) 0.53297(14) 0.0459(7) Uani 1 1 d . . . H17 H 0.6341 0.7071 0.4975 0.055 Uiso 1 1 calc R . . C18 C 0.6109(3) 0.64118(12) 0.53930(13) 0.0432(7) Uani 1 1 d . . . H18 H 0.5676 0.6254 0.5080 0.052 Uiso 1 1 calc R . . C19 C 0.6354(2) 0.61637(11) 0.59166(13) 0.0373(6) Uani 1 1 d . . . C20 C 0.6984(2) 0.64018(10) 0.64043(12) 0.0342(6) Uani 1 1 d . . . C21 C 0.6615(5) 0.42669(15) 0.8048(2) 0.0942(17) Uani 1 1 d . . . H21A H 0.7234 0.4028 0.8127 0.141 Uiso 1 1 calc R . . H21B H 0.6135 0.4169 0.7699 0.141 Uiso 1 1 calc R . . H21C H 0.6154 0.4277 0.8375 0.141 Uiso 1 1 calc R . . C22 C 0.5284(3) 0.54277(13) 0.55931(15) 0.0525(8) Uani 1 1 d . . . H22A H 0.4626 0.5635 0.5467 0.079 Uiso 1 1 calc R . . H22B H 0.5019 0.5118 0.5748 0.079 Uiso 1 1 calc R . . H22C H 0.5716 0.5358 0.5264 0.079 Uiso 1 1 calc R . . C23 C 0.6944(4) 0.43371(16) 0.6316(2) 0.0868(14) Uani 1 1 d . . . H23A H 0.7716 0.4458 0.6282 0.130 Uiso 1 1 calc R . . H23B H 0.6531 0.4309 0.5931 0.130 Uiso 1 1 calc R . . H23C H 0.6984 0.4013 0.6502 0.130 Uiso 1 1 calc R . . C24 C 0.4524(4) 0.52589(18) 0.7679(2) 0.0792(12) Uani 1 1 d . . . H24A H 0.4162 0.4948 0.7550 0.119 Uiso 1 1 calc R . . H24B H 0.3938 0.5493 0.7772 0.119 Uiso 1 1 calc R . . H24C H 0.5054 0.5200 0.8024 0.119 Uiso 1 1 calc R . . C25 C 0.3482(3) 0.63376(13) 0.63178(15) 0.0466(8) Uani 1 1 d . . . C26 C 0.2731(3) 0.59105(14) 0.61895(16) 0.0520(8) Uani 1 1 d . . . C27 C 0.2180(3) 0.58457(15) 0.56316(17) 0.0614(10) Uani 1 1 d . . . H27 H 0.1711 0.5565 0.5551 0.074 Uiso 1 1 calc R . . C28 C 0.2308(3) 0.61915(17) 0.51849(18) 0.0659(11) Uani 1 1 d . . . H28 H 0.1950 0.6134 0.4808 0.079 Uiso 1 1 calc R . . C29 C 0.2952(3) 0.66108(16) 0.52965(16) 0.0616(10) Uani 1 1 d . . . H29 H 0.3014 0.6845 0.4999 0.074 Uiso 1 1 calc R . . C30 C 0.3539(3) 0.66972(14) 0.58701(15) 0.0504(8) Uani 1 1 d . . . C31 C 0.4146(3) 0.71587(14) 0.59524(16) 0.0528(8) Uani 1 1 d . . . H31 H 0.4141 0.7371 0.5629 0.063 Uiso 1 1 calc R . . C32 C 0.5268(3) 0.77874(13) 0.64829(16) 0.0501(8) Uani 1 1 d . . . C33 C 0.5217(3) 0.81513(15) 0.60458(19) 0.0638(10) Uani 1 1 d . . . H33 H 0.4802 0.8089 0.5683 0.077 Uiso 1 1 calc R . . C34 C 0.5774(4) 0.86019(16) 0.6147(2) 0.0748(12) Uani 1 1 d . . . H34 H 0.5726 0.8844 0.5852 0.090 Uiso 1 1 calc R . . C35 C 0.6400(4) 0.87009(15) 0.6676(2) 0.0749(12) Uani 1 1 d . . . H35 H 0.6778 0.9008 0.6735 0.090 Uiso 1 1 calc R . . C36 C 0.6474(3) 0.83480(14) 0.71202(19) 0.0648(10) Uani 1 1 d . . . H36 H 0.6901 0.8416 0.7478 0.078 Uiso 1 1 calc R . . C37 C 0.5906(3) 0.78884(13) 0.70309(16) 0.0509(8) Uani 1 1 d . . . C38 C 0.6427(3) 0.75372(13) 0.79745(16) 0.0533(9) Uani 1 1 d . . . H38 H 0.6821 0.7837 0.8061 0.064 Uiso 1 1 calc R . . C39 C 0.6464(3) 0.71723(14) 0.84291(15) 0.0532(9) Uani 1 1 d . . . C40 C 0.7087(4) 0.73037(16) 0.89671(18) 0.0684(11) Uani 1 1 d . . . H40 H 0.7457 0.7614 0.9004 0.082 Uiso 1 1 calc R . . C41 C 0.7156(4) 0.69870(18) 0.94305(19) 0.0804(14) Uani 1 1 d . . . H41 H 0.7576 0.7079 0.9783 0.096 Uiso 1 1 calc R . . C42 C 0.6603(4) 0.65244(19) 0.93827(17) 0.0764(13) Uani 1 1 d . . . H42 H 0.6657 0.6310 0.9705 0.092 Uiso 1 1 calc R . . C43 C 0.5973(3) 0.63763(16) 0.88642(17) 0.0625(10) Uani 1 1 d . . . C44 C 0.5895(3) 0.67014(14) 0.83565(14) 0.0516(8) Uani 1 1 d . . . C45 C 0.1970(4) 0.51559(14) 0.6553(2) 0.0752(12) Uani 1 1 d . . . H45A H 0.1180 0.5239 0.6419 0.113 Uiso 1 1 calc R . . H45B H 0.1989 0.4967 0.6912 0.113 Uiso 1 1 calc R . . H45C H 0.2298 0.4958 0.6259 0.113 Uiso 1 1 calc R . . C46 C 0.5457(4) 0.5587(2) 0.9260(2) 0.0883(14) Uani 1 1 d . . . H46A H 0.6258 0.5523 0.9392 0.132 Uiso 1 1 calc R . . H46B H 0.5083 0.5278 0.9134 0.132 Uiso 1 1 calc R . . H46C H 0.5076 0.5727 0.9578 0.132 Uiso 1 1 calc R . . C47 C -0.0085(3) 0.63947(11) 0.60675(14) 0.0393(7) Uani 1 1 d . . . C48 C -0.0701(3) 0.61716(13) 0.55637(15) 0.0467(7) Uani 1 1 d . . . C49 C -0.0891(3) 0.64191(15) 0.50404(16) 0.0564(9) Uani 1 1 d . . . H49 H -0.1318 0.6266 0.4723 0.068 Uiso 1 1 calc R . . C50 C -0.0447(3) 0.69015(15) 0.49796(18) 0.0646(10) Uani 1 1 d . . . H50 H -0.0597 0.7072 0.4625 0.078 Uiso 1 1 calc R . . C51 C 0.0204(3) 0.71226(14) 0.54384(17) 0.0588(9) Uani 1 1 d . . . H51 H 0.0520 0.7439 0.5389 0.071 Uiso 1 1 calc R . . C52 C 0.0407(3) 0.68795(11) 0.59884(15) 0.0454(7) Uani 1 1 d . . . C53 C 0.1141(3) 0.71220(11) 0.64394(16) 0.0466(8) Uani 1 1 d . . . H53 H 0.1417 0.7439 0.6352 0.056 Uiso 1 1 calc R . . C54 C 0.2209(3) 0.72156(11) 0.73870(16) 0.0470(8) Uani 1 1 d . . . C55 C 0.2647(3) 0.77012(13) 0.73073(19) 0.0597(10) Uani 1 1 d . . . H55 H 0.2470 0.7870 0.6953 0.072 Uiso 1 1 calc R . . C56 C 0.3342(3) 0.79237(14) 0.7762(2) 0.0700(12) Uani 1 1 d . . . H56 H 0.3645 0.8242 0.7710 0.084 Uiso 1 1 calc R . . C57 C 0.3593(3) 0.76787(15) 0.8293(2) 0.0687(12) Uani 1 1 d . . . H57 H 0.4042 0.7838 0.8599 0.082 Uiso 1 1 calc R . . C58 C 0.3183(3) 0.72004(13) 0.83729(18) 0.0578(9) Uani 1 1 d . . . H58 H 0.3363 0.7036 0.8730 0.069 Uiso 1 1 calc R . . C59 C 0.2500(3) 0.69641(12) 0.79186(16) 0.0485(8) Uani 1 1 d . . . C60 C 0.2290(3) 0.61777(13) 0.83848(15) 0.0487(8) Uani 1 1 d . . . H60 H 0.2809 0.6299 0.8690 0.058 Uiso 1 1 calc R . . C61 C 0.1864(3) 0.56776(12) 0.84462(14) 0.0465(7) Uani 1 1 d . . . C62 C 0.2307(3) 0.53952(14) 0.89453(16) 0.0614(10) Uani 1 1 d . . . H62 H 0.2817 0.5547 0.9234 0.074 Uiso 1 1 calc R . . C63 C 0.2001(4) 0.49085(15) 0.90103(18) 0.0701(11) Uani 1 1 d . . . H63 H 0.2311 0.4729 0.9338 0.084 Uiso 1 1 calc R . . C64 C 0.1223(3) 0.46756(13) 0.85881(17) 0.0594(9) Uani 1 1 d . . . H64 H 0.1022 0.4341 0.8634 0.071 Uiso 1 1 calc R . . C65 C 0.0758(3) 0.49371(12) 0.81090(15) 0.0472(7) Uani 1 1 d . . . C66 C 0.1046(3) 0.54517(11) 0.80189(13) 0.0397(7) Uani 1 1 d . . . C67 C -0.1542(4) 0.54043(16) 0.51821(17) 0.0721(11) Uani 1 1 d . . . H67A H -0.2201 0.5574 0.4983 0.108 Uiso 1 1 calc R . . H67B H -0.1778 0.5080 0.5312 0.108 Uiso 1 1 calc R . . H67C H -0.0953 0.5364 0.4918 0.108 Uiso 1 1 calc R . . C68 C -0.0170(6) 0.42255(15) 0.7647(3) 0.125(2) Uani 1 1 d . . . H68A H 0.0570 0.4069 0.7620 0.188 Uiso 1 1 calc R . . H68B H -0.0690 0.4139 0.7307 0.188 Uiso 1 1 calc R . . H68C H -0.0489 0.4111 0.7996 0.188 Uiso 1 1 calc R . . C69 C 0.0930(5) 0.3412(2) 0.9238(3) 0.1019(17) Uani 1 1 d . . . H69A H 0.1676 0.3389 0.9088 0.153 Uiso 1 1 calc R . . H69B H 0.0844 0.3140 0.9506 0.153 Uiso 1 1 calc R . . H69C H 0.0874 0.3726 0.9440 0.153 Uiso 1 1 calc R . . Cl1 Cl 0.38032(8) 0.39282(3) 0.63137(4) 0.0558(2) Uani 1 1 d . . . Cl2 Cl 0.76894(8) 0.34107(3) 0.98266(4) 0.0617(2) Uani 1 1 d . . . Cu1 Cu 0.80925(3) 0.632874(12) 0.758353(15) 0.03652(11) Uani 1 1 d . . . Cu2 Cu 0.49722(3) 0.691313(15) 0.716411(17) 0.04546(12) Uani 1 1 d . . . Cu3 Cu 0.10227(3) 0.629320(12) 0.724203(16) 0.03802(11) Uani 1 1 d . . . Fe1 Fe 0.68576(4) 0.536231(15) 0.704884(19) 0.03897(12) Uani 1 1 d . . . H5C H 0.911(2) 0.5217(12) 0.7038(11) 0.040(9) Uiso 1 1 d D . . H5D H 0.886(3) 0.5434(13) 0.6555(16) 0.074(14) Uiso 1 1 d D . . H6D H 0.487(3) 0.5729(9) 0.7115(15) 0.052(11) Uiso 1 1 d D . . H7D H 0.5682(19) 0.4583(13) 0.6681(16) 0.057(11) Uiso 1 1 d D . . N1 N 0.9019(2) 0.65115(9) 0.82933(11) 0.0373(5) Uani 1 1 d . . . N2 N 0.8472(2) 0.69864(8) 0.73001(11) 0.0359(5) Uani 1 1 d . . . N3 N 0.4713(2) 0.73109(10) 0.64438(12) 0.0469(6) Uani 1 1 d . . . N4 N 0.5895(2) 0.74919(10) 0.74494(12) 0.0486(7) Uani 1 1 d . . . N5 N 0.1464(2) 0.69473(9) 0.69572(12) 0.0432(6) Uani 1 1 d . . . N6 N 0.2022(2) 0.64755(9) 0.79479(12) 0.0420(6) Uani 1 1 d . . . O1 O 0.77036(18) 0.56735(7) 0.78312(9) 0.0404(5) Uani 1 1 d . . . O2 O 0.71441(18) 0.61410(7) 0.68988(9) 0.0404(5) Uani 1 1 d . . . O3 O 0.7096(2) 0.47526(8) 0.79625(10) 0.0569(6) Uani 1 1 d . . . O4 O 0.60151(19) 0.56836(8) 0.60403(9) 0.0458(5) Uani 1 1 d . . . O5 O 0.8553(2) 0.52344(9) 0.67737(11) 0.0474(5) Uani 1 1 d D . . O6 O 0.5143(2) 0.54601(9) 0.72230(11) 0.0551(6) Uani 1 1 d D . . O7 O 0.6352(2) 0.46773(8) 0.66599(11) 0.0542(6) Uani 1 1 d D . . O8 O 0.40441(19) 0.63624(8) 0.68458(10) 0.0491(5) Uani 1 1 d . . . O9 O 0.5311(2) 0.65408(9) 0.78763(10) 0.0571(6) Uani 1 1 d . . . O10 O 0.2628(2) 0.56045(10) 0.66554(12) 0.0641(7) Uani 1 1 d . . . O11 O 0.5389(3) 0.59302(12) 0.87848(12) 0.0756(8) Uani 1 1 d . . . O12 O 0.00064(17) 0.61411(7) 0.65582(9) 0.0417(5) Uani 1 1 d . . . O13 O 0.05376(18) 0.56766(7) 0.75535(9) 0.0435(5) Uani 1 1 d . . . O14 O -0.1095(2) 0.56905(8) 0.56732(10) 0.0539(6) Uani 1 1 d . . . O15 O -0.0029(2) 0.47466(8) 0.76725(11) 0.0602(6) Uani 1 1 d . . . O24 O 0.0065(5) 0.33848(16) 0.87770(19) 0.1145(12) Uani 1 1 d D . . O17 O 0.4375(4) 0.34928(12) 0.61407(19) 0.1159(13) Uani 1 1 d . . . O18 O 0.2645(3) 0.38122(14) 0.64092(17) 0.1070(12) Uani 1 1 d . . . O19 O 0.3842(3) 0.42961(10) 0.58710(13) 0.0851(9) Uani 1 1 d . . . O16 O 0.4401(3) 0.41207(16) 0.68375(13) 0.1168(14) Uani 1 1 d . . . O21 O 0.6826(3) 0.37761(14) 0.98687(19) 0.1214(14) Uani 1 1 d . . . O22 O 0.7757(3) 0.33107(14) 0.92182(14) 0.0984(10) Uani 1 1 d . . . O23 O 0.8767(3) 0.35961(15) 1.00896(17) 0.1136(13) Uani 1 1 d . . . O20 O 0.7394(4) 0.29683(15) 1.01019(18) 0.1344(16) Uani 1 1 d . . . H24M H -0.062(4) 0.331(4) 0.886(5) 0.29(6) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0375(15) 0.0425(15) 0.0310(16) 0.0030(12) 0.0034(12) 0.0028(12) C2 0.0451(17) 0.0478(17) 0.0397(18) 0.0071(14) -0.0015(14) -0.0015(14) C3 0.064(2) 0.0471(18) 0.057(2) 0.0183(16) -0.0013(18) -0.0036(16) C4 0.074(2) 0.066(2) 0.0378(19) 0.0156(16) -0.0091(17) 0.0058(18) C5 0.063(2) 0.0526(19) 0.0355(18) 0.0013(14) -0.0097(15) 0.0062(16) C6 0.0436(16) 0.0438(16) 0.0320(16) -0.0005(12) -0.0013(13) 0.0050(13) C7 0.0419(17) 0.0464(17) 0.0339(17) -0.0106(13) -0.0018(13) 0.0025(13) C8 0.0367(15) 0.0378(15) 0.0443(18) -0.0148(13) 0.0085(13) -0.0016(12) C9 0.0494(19) 0.0508(18) 0.046(2) -0.0121(15) 0.0017(15) -0.0028(15) C10 0.056(2) 0.0505(19) 0.060(2) -0.0276(17) 0.0066(17) -0.0134(16) C11 0.063(2) 0.0405(17) 0.069(3) -0.0153(17) 0.0089(19) -0.0117(15) C12 0.059(2) 0.0347(16) 0.058(2) -0.0040(15) 0.0095(16) -0.0038(14) C13 0.0359(15) 0.0345(14) 0.0467(18) -0.0101(13) 0.0086(13) 0.0011(12) C14 0.0389(15) 0.0315(14) 0.0440(18) 0.0000(12) 0.0115(13) 0.0050(12) C15 0.0349(15) 0.0330(14) 0.0357(16) 0.0016(11) 0.0078(12) 0.0037(11) C16 0.0446(17) 0.0390(15) 0.0432(18) 0.0076(13) 0.0092(14) 0.0017(13) C17 0.0552(19) 0.0500(18) 0.0330(17) 0.0093(13) 0.0070(14) 0.0060(15) C18 0.0433(17) 0.0556(18) 0.0304(16) -0.0002(13) 0.0017(13) 0.0040(14) C19 0.0360(15) 0.0400(15) 0.0362(17) 0.0009(12) 0.0055(12) 0.0035(12) C20 0.0350(15) 0.0375(14) 0.0301(15) 0.0009(11) 0.0036(12) 0.0041(11) C21 0.126(4) 0.062(3) 0.087(3) 0.018(2) -0.032(3) -0.041(3) C22 0.0521(19) 0.0530(19) 0.050(2) -0.0073(15) -0.0072(16) -0.0097(15) C23 0.084(3) 0.062(2) 0.115(4) -0.036(3) 0.017(3) -0.008(2) C24 0.081(3) 0.094(3) 0.065(3) 0.009(2) 0.018(2) -0.002(2) C25 0.0341(16) 0.063(2) 0.0424(19) -0.0176(15) 0.0014(14) 0.0110(14) C26 0.0356(17) 0.066(2) 0.055(2) -0.0197(17) 0.0051(15) 0.0061(15) C27 0.0435(19) 0.073(2) 0.066(3) -0.030(2) -0.0038(17) 0.0107(17) C28 0.053(2) 0.094(3) 0.048(2) -0.028(2) -0.0093(17) 0.012(2) C29 0.051(2) 0.089(3) 0.043(2) -0.0101(19) -0.0023(16) 0.0112(19) C30 0.0396(17) 0.067(2) 0.0443(19) -0.0104(16) 0.0035(14) 0.0098(15) C31 0.0430(18) 0.068(2) 0.047(2) -0.0062(17) 0.0033(15) 0.0124(16) C32 0.0416(17) 0.0551(19) 0.054(2) -0.0058(16) 0.0086(15) 0.0099(14) C33 0.060(2) 0.067(2) 0.065(3) 0.0042(19) 0.0074(19) 0.0066(18) C34 0.075(3) 0.071(3) 0.082(3) 0.004(2) 0.022(2) 0.009(2) C35 0.079(3) 0.057(2) 0.093(4) -0.008(2) 0.030(3) -0.006(2) C36 0.064(2) 0.064(2) 0.068(3) -0.018(2) 0.0121(19) -0.0014(19) C37 0.0453(18) 0.0542(19) 0.055(2) -0.0098(16) 0.0125(15) 0.0069(15) C38 0.0422(18) 0.058(2) 0.059(2) -0.0223(17) 0.0037(16) 0.0094(15) C39 0.0459(18) 0.065(2) 0.048(2) -0.0230(17) -0.0038(15) 0.0153(16) C40 0.070(3) 0.075(3) 0.057(2) -0.025(2) -0.0103(19) 0.019(2) C41 0.089(3) 0.089(3) 0.057(3) -0.033(2) -0.020(2) 0.021(3) C42 0.086(3) 0.098(3) 0.043(2) -0.011(2) -0.005(2) 0.029(3) C43 0.059(2) 0.077(3) 0.051(2) -0.0113(19) 0.0041(18) 0.0172(19) C44 0.0448(18) 0.069(2) 0.0396(19) -0.0137(16) 0.0002(14) 0.0167(16) C45 0.072(3) 0.058(2) 0.095(3) -0.022(2) 0.006(2) -0.004(2) C46 0.086(3) 0.108(4) 0.072(3) 0.023(3) 0.012(3) -0.002(3) C47 0.0359(16) 0.0407(15) 0.0421(18) 0.0059(13) 0.0076(13) 0.0085(12) C48 0.0408(17) 0.0555(19) 0.0440(19) 0.0015(15) 0.0053(14) 0.0072(14) C49 0.0473(19) 0.077(2) 0.045(2) 0.0095(17) 0.0037(15) 0.0068(17) C50 0.054(2) 0.084(3) 0.056(2) 0.029(2) 0.0066(18) 0.0113(19) C51 0.054(2) 0.059(2) 0.065(2) 0.0234(18) 0.0132(18) 0.0063(17) C52 0.0384(16) 0.0438(17) 0.055(2) 0.0093(14) 0.0107(14) 0.0073(13) C53 0.0444(17) 0.0337(15) 0.064(2) 0.0028(15) 0.0164(16) 0.0002(13) C54 0.0360(16) 0.0415(16) 0.066(2) -0.0166(15) 0.0172(15) -0.0049(13) C55 0.054(2) 0.0435(18) 0.084(3) -0.0130(18) 0.0200(19) -0.0074(15) C56 0.054(2) 0.046(2) 0.114(4) -0.024(2) 0.025(2) -0.0149(17) C57 0.049(2) 0.063(2) 0.095(3) -0.036(2) 0.010(2) -0.0133(18) C58 0.0445(19) 0.056(2) 0.073(3) -0.0222(18) 0.0069(17) -0.0064(15) C59 0.0385(17) 0.0431(17) 0.066(2) -0.0160(16) 0.0157(16) -0.0050(13) C60 0.0440(18) 0.0564(19) 0.045(2) -0.0155(16) 0.0003(15) -0.0041(15) C61 0.0465(18) 0.0533(18) 0.0394(18) -0.0023(14) 0.0029(14) 0.0041(14) C62 0.064(2) 0.067(2) 0.051(2) -0.0061(18) -0.0083(18) 0.0029(18) C63 0.086(3) 0.068(2) 0.054(2) 0.0131(19) -0.007(2) 0.012(2) C64 0.072(2) 0.0470(19) 0.057(2) 0.0084(16) -0.0003(19) 0.0038(17) C65 0.0504(18) 0.0439(17) 0.0465(19) 0.0019(14) 0.0013(15) 0.0030(14) C66 0.0397(16) 0.0416(16) 0.0384(17) -0.0073(13) 0.0079(13) 0.0024(12) C67 0.081(3) 0.076(3) 0.056(2) -0.018(2) -0.008(2) -0.005(2) C68 0.164(6) 0.039(2) 0.155(5) -0.001(3) -0.074(4) -0.009(3) C69 0.101(4) 0.084(3) 0.119(5) 0.030(3) 0.006(4) 0.002(3) Cl1 0.0659(5) 0.0455(4) 0.0526(5) 0.0063(4) -0.0109(4) -0.0107(4) Cl2 0.0696(6) 0.0557(5) 0.0566(6) -0.0049(4) -0.0102(4) -0.0016(4) Cu1 0.0444(2) 0.03194(19) 0.0320(2) -0.00031(14) -0.00235(15) -0.00427(14) Cu2 0.0424(2) 0.0534(2) 0.0398(2) -0.01076(17) -0.00034(17) 0.00479(16) Cu3 0.0408(2) 0.03271(19) 0.0409(2) -0.00456(14) 0.00545(16) -0.00252(14) Fe1 0.0415(2) 0.0349(2) 0.0394(3) -0.00158(17) -0.00152(19) -0.00682(17) N1 0.0387(13) 0.0358(12) 0.0371(14) -0.0056(11) 0.0017(11) 0.0008(10) N2 0.0381(13) 0.0336(12) 0.0362(14) -0.0037(10) 0.0047(10) 0.0002(10) N3 0.0403(14) 0.0569(16) 0.0436(16) -0.0061(12) 0.0044(12) 0.0086(12) N4 0.0427(15) 0.0559(16) 0.0469(17) -0.0162(13) 0.0031(12) 0.0063(12) N5 0.0420(14) 0.0340(12) 0.0560(18) -0.0053(12) 0.0162(12) -0.0001(10) N6 0.0372(14) 0.0399(13) 0.0495(16) -0.0122(12) 0.0077(12) -0.0043(11) O1 0.0497(12) 0.0369(10) 0.0326(11) 0.0056(8) -0.0062(9) -0.0071(9) O2 0.0501(12) 0.0370(10) 0.0321(11) 0.0059(9) -0.0061(9) -0.0071(9) O3 0.0738(16) 0.0418(12) 0.0516(14) 0.0064(10) -0.0117(12) -0.0168(11) O4 0.0555(13) 0.0418(11) 0.0377(12) 0.0009(9) -0.0065(10) -0.0102(10) O5 0.0437(13) 0.0486(13) 0.0488(15) 0.0037(11) -0.0004(11) -0.0039(10) O6 0.0473(13) 0.0542(15) 0.0648(16) 0.0095(12) 0.0105(12) 0.0015(11) O7 0.0593(16) 0.0451(13) 0.0576(15) -0.0095(11) 0.0034(12) -0.0145(11) O8 0.0475(13) 0.0577(13) 0.0407(13) -0.0097(10) -0.0025(10) 0.0019(10) O9 0.0653(15) 0.0617(15) 0.0416(14) -0.0082(11) -0.0074(11) 0.0038(12) O10 0.0600(15) 0.0636(15) 0.0671(17) -0.0092(13) -0.0010(13) -0.0059(12) O11 0.0813(19) 0.088(2) 0.0554(17) 0.0103(15) -0.0034(14) -0.0017(16) O12 0.0463(12) 0.0371(10) 0.0407(12) 0.0024(9) -0.0003(9) -0.0033(9) O13 0.0488(12) 0.0383(11) 0.0417(12) 0.0020(9) -0.0030(10) -0.0070(9) O14 0.0586(14) 0.0553(14) 0.0452(13) -0.0044(10) -0.0072(11) -0.0045(11) O15 0.0755(17) 0.0354(11) 0.0650(16) 0.0005(11) -0.0167(13) -0.0084(11) O24 0.145(4) 0.110(3) 0.089(3) 0.018(2) 0.012(3) -0.018(3) O17 0.134(3) 0.0640(19) 0.146(3) 0.005(2) -0.007(3) 0.028(2) O18 0.066(2) 0.128(3) 0.125(3) 0.020(2) -0.0064(19) -0.0294(19) O19 0.125(3) 0.0603(17) 0.0709(19) 0.0201(14) 0.0152(18) 0.0058(16) O16 0.126(3) 0.173(4) 0.0488(18) -0.003(2) -0.0042(18) -0.081(3) O21 0.107(3) 0.113(3) 0.140(4) -0.051(2) -0.011(2) 0.032(2) O22 0.102(2) 0.129(3) 0.061(2) -0.0177(19) -0.0077(17) 0.007(2) O23 0.084(2) 0.144(3) 0.104(3) -0.010(2) -0.032(2) -0.030(2) O20 0.192(5) 0.099(3) 0.109(3) 0.028(2) -0.002(3) -0.040(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.324(3) . ? C1 C6 1.412(4) . ? C1 C2 1.418(4) . ? C2 C3 1.371(4) . ? C2 O3 1.376(4) . ? C3 C4 1.380(5) . ? C3 H3 0.9300 . ? C4 C5 1.364(5) . ? C4 H4 0.9300 . ? C5 C6 1.414(4) . ? C5 H5 0.9300 . ? C6 C7 1.444(4) . ? C7 N1 1.296(4) . ? C7 H7 0.9300 . ? C8 C9 1.388(4) . ? C8 C13 1.407(4) . ? C8 N1 1.421(4) . ? C9 C10 1.376(5) . ? C9 H9 0.9300 . ? C10 C11 1.383(5) . ? C10 H10 0.9300 . ? C11 C12 1.370(5) . ? C11 H11 0.9300 . ? C12 C13 1.399(4) . ? C12 H12 0.9300 . ? C13 N2 1.423(4) . ? C14 N2 1.289(4) . ? C14 C15 1.430(4) . ? C14 H14 0.9300 . ? C15 C20 1.413(4) . ? C15 C16 1.414(4) . ? C16 C17 1.357(4) . ? C16 H16 0.9300 . ? C17 C18 1.398(4) . ? C17 H17 0.9300 . ? C18 C19 1.370(4) . ? C18 H18 0.9300 . ? C19 O4 1.375(3) . ? C19 C20 1.417(4) . ? C20 O2 1.322(3) . ? C21 O3 1.429(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O4 1.431(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O7 1.418(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O6 1.426(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O8 1.312(4) . ? C25 C30 1.407(5) . ? C25 C26 1.443(5) . ? C26 O10 1.354(4) . ? C26 C27 1.377(5) . ? C27 C28 1.393(6) . ? C27 H27 0.9300 . ? C28 C29 1.352(6) . ? C28 H28 0.9300 . ? C29 C30 1.432(5) . ? C29 H29 0.9300 . ? C30 C31 1.419(5) . ? C31 N3 1.306(4) . ? C31 H31 0.9300 . ? C32 C33 1.388(5) . ? C32 C37 1.413(5) . ? C32 N3 1.421(4) . ? C33 C34 1.371(6) . ? C33 H33 0.9300 . ? C34 C35 1.370(6) . ? C34 H34 0.9300 . ? C35 C36 1.379(6) . ? C35 H35 0.9300 . ? C36 C37 1.394(5) . ? C36 H36 0.9300 . ? C37 N4 1.425(5) . ? C38 N4 1.297(4) . ? C38 C39 1.419(5) . ? C38 H38 0.9300 . ? C39 C40 1.404(5) . ? C39 C44 1.418(5) . ? C40 C41 1.349(6) . ? C40 H40 0.9300 . ? C41 C42 1.387(6) . ? C41 H41 0.9300 . ? C42 C43 1.384(5) . ? C42 H42 0.9300 . ? C43 O11 1.369(5) . ? C43 C44 1.442(5) . ? C44 O9 1.301(4) . ? C45 O10 1.423(4) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 O11 1.416(5) . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 O12 1.303(4) . ? C47 C48 1.421(5) . ? C47 C52 1.429(4) . ? C48 C49 1.363(5) . ? C48 O14 1.391(4) . ? C49 C50 1.396(5) . ? C49 H49 0.9300 . ? C50 C51 1.361(5) . ? C50 H50 0.9300 . ? C51 C52 1.411(5) . ? C51 H51 0.9300 . ? C52 C53 1.422(5) . ? C53 N5 1.290(4) . ? C53 H53 0.9300 . ? C54 C59 1.397(5) . ? C54 C55 1.407(5) . ? C54 N5 1.430(4) . ? C55 C56 1.381(6) . ? C55 H55 0.9300 . ? C56 C57 1.382(6) . ? C56 H56 0.9300 . ? C57 C58 1.377(5) . ? C57 H57 0.9300 . ? C58 C59 1.389(5) . ? C58 H58 0.9300 . ? C59 N6 1.418(4) . ? C60 N6 1.288(4) . ? C60 C61 1.431(5) . ? C60 H60 0.9300 . ? C61 C62 1.417(5) . ? C61 C66 1.422(4) . ? C62 C63 1.356(5) . ? C62 H62 0.9300 . ? C63 C64 1.396(5) . ? C63 H63 0.9300 . ? C64 C65 1.361(5) . ? C64 H64 0.9300 . ? C65 O15 1.377(4) . ? C65 C66 1.430(4) . ? C66 O13 1.307(4) . ? C67 O14 1.410(4) . ? C67 H67A 0.9600 . ? C67 H67B 0.9600 . ? C67 H67C 0.9600 . ? C68 O15 1.398(4) . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? C69 O24 1.379(7) . ? C69 H69A 0.9600 . ? C69 H69B 0.9600 . ? C69 H69C 0.9600 . ? Cl1 O17 1.410(3) . ? Cl1 O18 1.411(3) . ? Cl1 O19 1.411(3) . ? Cl1 O16 1.416(3) . ? Cl2 O20 1.394(4) . ? Cl2 O21 1.404(3) . ? Cl2 O23 1.416(3) . ? Cl2 O22 1.423(3) . ? Cu1 O2 1.8847(19) . ? Cu1 O1 1.9019(19) . ? Cu1 N1 1.913(2) . ? Cu1 N2 1.933(2) . ? Cu2 O9 1.911(2) . ? Cu2 O8 1.917(2) . ? Cu2 N4 1.949(3) . ? Cu2 N3 1.953(3) . ? Cu3 O13 1.896(2) . ? Cu3 O12 1.901(2) . ? Cu3 N5 1.945(3) . ? Cu3 N6 1.948(3) . ? Fe1 O6 2.075(2) . ? Fe1 O7 2.087(2) . ? Fe1 O1 2.117(2) . ? Fe1 O2 2.133(2) . ? Fe1 O5 2.144(2) . ? O5 H5C 0.834(18) . ? O5 H5D 0.835(19) . ? O6 H6D 0.809(18) . ? O7 H7D 0.819(18) . ? O24 H24M 0.85(2) . ? 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 C6 124.2(3) . . ? O1 C1 C2 117.3(3) . . ? C6 C1 C2 118.5(3) . . ? C3 C2 O3 125.9(3) . . ? C3 C2 C1 120.5(3) . . ? O3 C2 C1 113.5(3) . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.6(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 C7 124.1(3) . . ? C5 C6 C7 117.0(3) . . ? N1 C7 C6 125.7(3) . . ? N1 C7 H7 117.1 . . ? C6 C7 H7 117.1 . . ? C9 C8 C13 119.3(3) . . ? C9 C8 N1 125.5(3) . . ? C13 C8 N1 115.2(3) . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.0(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 121.4(3) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 119.2(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C12 C13 C8 119.8(3) . . ? C12 C13 N2 125.0(3) . . ? C8 C13 N2 115.2(2) . . ? N2 C14 C15 126.3(3) . . ? N2 C14 H14 116.9 . . ? C15 C14 H14 116.9 . . ? C20 C15 C16 118.2(3) . . ? C20 C15 C14 123.5(3) . . ? C16 C15 C14 118.3(3) . . ? C17 C16 C15 121.7(3) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 O4 126.1(3) . . ? C18 C19 C20 121.0(3) . . ? O4 C19 C20 112.9(2) . . ? O2 C20 C15 124.3(3) . . ? O2 C20 C19 116.9(2) . . ? C15 C20 C19 118.8(3) . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O7 C23 H23A 109.5 . . ? O7 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O7 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 C30 125.3(3) . . ? O8 C25 C26 117.3(3) . . ? C30 C25 C26 117.4(3) . . ? O10 C26 C27 125.6(3) . . ? O10 C26 C25 114.4(3) . . ? C27 C26 C25 120.0(4) . . ? C26 C27 C28 121.4(4) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C29 C28 C27 120.3(4) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C28 C29 C30 120.4(4) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C25 C30 C31 123.5(3) . . ? C25 C30 C29 120.2(3) . . ? C31 C30 C29 116.3(3) . . ? N3 C31 C30 125.6(3) . . ? N3 C31 H31 117.2 . . ? C30 C31 H31 117.2 . . ? C33 C32 C37 119.0(3) . . ? C33 C32 N3 126.3(3) . . ? C37 C32 N3 114.7(3) . . ? C34 C33 C32 120.3(4) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C35 C34 C33 121.0(4) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? C34 C35 C36 120.4(4) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C37 119.8(4) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C36 C37 C32 119.5(4) . . ? C36 C37 N4 126.0(3) . . ? C32 C37 N4 114.4(3) . . ? N4 C38 C39 126.1(3) . . ? N4 C38 H38 117.0 . . ? C39 C38 H38 117.0 . . ? C40 C39 C44 120.9(4) . . ? C40 C39 C38 116.4(4) . . ? C44 C39 C38 122.7(3) . . ? C41 C40 C39 121.0(4) . . ? C41 C40 H40 119.5 . . ? C39 C40 H40 119.5 . . ? C40 C41 C42 120.2(4) . . ? C40 C41 H41 119.9 . . ? C42 C41 H41 119.9 . . ? C43 C42 C41 121.3(4) . . ? C43 C42 H42 119.4 . . ? C41 C42 H42 119.4 . . ? O11 C43 C42 124.8(4) . . ? O11 C43 C44 115.1(3) . . ? C42 C43 C44 120.1(4) . . ? O9 C44 C39 125.8(3) . . ? O9 C44 C43 117.7(3) . . ? C39 C44 C43 116.5(3) . . ? O10 C45 H45A 109.5 . . ? O10 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? O10 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O11 C46 H46A 109.5 . . ? O11 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O11 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? O12 C47 C48 118.0(3) . . ? O12 C47 C52 125.3(3) . . ? C48 C47 C52 116.7(3) . . ? C49 C48 O14 125.2(3) . . ? C49 C48 C47 122.1(3) . . ? O14 C48 C47 112.7(3) . . ? C48 C49 C50 120.2(4) . . ? C48 C49 H49 119.9 . . ? C50 C49 H49 119.9 . . ? C51 C50 C49 120.1(3) . . ? C51 C50 H50 119.9 . . ? C49 C50 H50 119.9 . . ? C50 C51 C52 121.1(3) . . ? C50 C51 H51 119.5 . . ? C52 C51 H51 119.5 . . ? C51 C52 C53 118.0(3) . . ? C51 C52 C47 119.6(3) . . ? C53 C52 C47 122.3(3) . . ? N5 C53 C52 126.6(3) . . ? N5 C53 H53 116.7 . . ? C52 C53 H53 116.7 . . ? C59 C54 C55 119.7(3) . . ? C59 C54 N5 115.6(3) . . ? C55 C54 N5 124.7(3) . . ? C56 C55 C54 119.1(4) . . ? C56 C55 H55 120.4 . . ? C54 C55 H55 120.4 . . ? C55 C56 C57 120.8(4) . . ? C55 C56 H56 119.6 . . ? C57 C56 H56 119.6 . . ? C58 C57 C56 120.5(4) . . ? C58 C57 H57 119.8 . . ? C56 C57 H57 119.8 . . ? C57 C58 C59 119.9(4) . . ? C57 C58 H58 120.1 . . ? C59 C58 H58 120.1 . . ? C58 C59 C54 120.0(3) . . ? C58 C59 N6 125.1(3) . . ? C54 C59 N6 114.8(3) . . ? N6 C60 C61 126.2(3) . . ? N6 C60 H60 116.9 . . ? C61 C60 H60 116.9 . . ? C62 C61 C66 119.3(3) . . ? C62 C61 C60 118.2(3) . . ? C66 C61 C60 122.5(3) . . ? C63 C62 C61 121.2(3) . . ? C63 C62 H62 119.4 . . ? C61 C62 H62 119.4 . . ? C62 C63 C64 120.4(3) . . ? C62 C63 H63 119.8 . . ? C64 C63 H63 119.8 . . ? C65 C64 C63 120.2(3) . . ? C65 C64 H64 119.9 . . ? C63 C64 H64 119.9 . . ? C64 C65 O15 124.9(3) . . ? C64 C65 C66 121.8(3) . . ? O15 C65 C66 113.3(3) . . ? O13 C66 C61 125.3(3) . . ? O13 C66 C65 117.6(3) . . ? C61 C66 C65 117.1(3) . . ? O14 C67 H67A 109.5 . . ? O14 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? O14 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? O15 C68 H68A 109.5 . . ? O15 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? O15 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? O24 C69 H69A 109.5 . . ? O24 C69 H69B 109.5 . . ? H69A C69 H69B 109.5 . . ? O24 C69 H69C 109.5 . . ? H69A C69 H69C 109.5 . . ? H69B C69 H69C 109.5 . . ? O17 Cl1 O18 110.0(2) . . ? O17 Cl1 O19 108.7(2) . . ? O18 Cl1 O19 111.2(2) . . ? O17 Cl1 O16 109.3(3) . . ? O18 Cl1 O16 109.8(2) . . ? O19 Cl1 O16 107.8(2) . . ? O20 Cl2 O21 110.3(3) . . ? O20 Cl2 O23 110.4(3) . . ? O21 Cl2 O23 109.3(2) . . ? O20 Cl2 O22 108.7(2) . . ? O21 Cl2 O22 107.8(2) . . ? O23 Cl2 O22 110.3(2) . . ? O2 Cu1 O1 82.41(8) . . ? O2 Cu1 N1 178.19(10) . . ? O1 Cu1 N1 96.35(9) . . ? O2 Cu1 N2 95.48(9) . . ? O1 Cu1 N2 177.75(9) . . ? N1 Cu1 N2 85.78(10) . . ? O9 Cu2 O8 89.13(10) . . ? O9 Cu2 N4 93.86(11) . . ? O8 Cu2 N4 177.01(11) . . ? O9 Cu2 N3 176.75(11) . . ? O8 Cu2 N3 93.61(11) . . ? N4 Cu2 N3 83.40(12) . . ? O13 Cu3 O12 86.65(9) . . ? O13 Cu3 N5 176.42(10) . . ? O12 Cu3 N5 94.46(10) . . ? O13 Cu3 N6 94.53(10) . . ? O12 Cu3 N6 177.45(10) . . ? N5 Cu3 N6 84.23(12) . . ? O6 Fe1 O7 87.64(10) . . ? O6 Fe1 O1 99.14(9) . . ? O7 Fe1 O1 141.92(9) . . ? O6 Fe1 O2 94.31(9) . . ? O7 Fe1 O2 145.39(9) . . ? O1 Fe1 O2 71.87(7) . . ? O6 Fe1 O5 173.66(10) . . ? O7 Fe1 O5 87.82(10) . . ? O1 Fe1 O5 87.16(9) . . ? O2 Fe1 O5 86.92(9) . . ? C7 N1 C8 123.5(3) . . ? C7 N1 Cu1 124.2(2) . . ? C8 N1 Cu1 112.29(19) . . ? C14 N2 C13 124.3(2) . . ? C14 N2 Cu1 124.1(2) . . ? C13 N2 Cu1 111.54(19) . . ? C31 N3 C32 121.1(3) . . ? C31 N3 Cu2 125.2(3) . . ? C32 N3 Cu2 113.7(2) . . ? C38 N4 C37 121.0(3) . . ? C38 N4 Cu2 125.1(3) . . ? C37 N4 Cu2 113.8(2) . . ? C53 N5 C54 123.2(3) . . ? C53 N5 Cu3 124.6(2) . . ? C54 N5 Cu3 112.2(2) . . ? C60 N6 C59 122.5(3) . . ? C60 N6 Cu3 124.3(2) . . ? C59 N6 Cu3 113.0(2) . . ? C1 O1 Cu1 125.36(18) . . ? C1 O1 Fe1 131.75(18) . . ? Cu1 O1 Fe1 102.21(9) . . ? C20 O2 Cu1 126.05(18) . . ? C20 O2 Fe1 129.56(18) . . ? Cu1 O2 Fe1 102.21(8) . . ? C2 O3 C21 116.6(3) . . ? C19 O4 C22 117.2(2) . . ? Fe1 O5 H5C 117(2) . . ? Fe1 O5 H5D 122(3) . . ? H5C O5 H5D 97(4) . . ? C24 O6 Fe1 130.6(2) . . ? C24 O6 H6D 110(3) . . ? Fe1 O6 H6D 114(3) . . ? C23 O7 Fe1 131.6(2) . . ? C23 O7 H7D 110(3) . . ? Fe1 O7 H7D 118(3) . . ? C25 O8 Cu2 126.4(2) . . ? C44 O9 Cu2 126.2(2) . . ? C26 O10 C45 117.6(3) . . ? C43 O11 C46 118.0(3) . . ? C47 O12 Cu3 125.83(19) . . ? C66 O13 Cu3 125.15(18) . . ? C48 O14 C67 117.1(3) . . ? C65 O15 C68 117.5(3) . . ? C69 O24 H24M 117(8) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.58 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.442 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 930931'