# 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_L1 _audit_creation_date 2013-08-27 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H40 N8' _chemical_formula_sum 'C40 H40 N8' _chemical_formula_weight 632.80 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 9.1779(4) _cell_length_b 23.8787(13) _cell_length_c 7.9118(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.095(2) _cell_angle_gamma 90.00 _cell_volume 1733.60(15) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2340 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 27.42 _cell_measurement_theta_min 3.41 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.7021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0605 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.9410. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_unetI/netI 0.0652 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 15973 _diffrn_reflns_theta_full 30.60 _diffrn_reflns_theta_max 30.60 _diffrn_reflns_theta_min 2.80 _diffrn_ambient_temperature 120.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3517 _reflns_number_total 5265 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.357 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.051 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 5265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0538 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.0824P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1085 _refine_ls_wR_factor_ref 0.1228 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C6(H6A,H6B), C16(H16A,H16B), C3(H3A,H3B) 2.b Aromatic/amide H refined with riding coordinates: C22(H22), C21(H21), C19(H19), C9(H9), C13(H13), C18(H18), C12(H12), C10(H10) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 N1 N 0.07812(11) 0.57986(4) 0.17937(12) 0.0176(2) Uani 1 1 d . . . N4 N -0.17764(11) 0.48838(4) 0.15534(12) 0.0183(2) Uani 1 1 d . . . C2 C 0.07044(14) 0.52129(5) 0.23367(15) 0.0187(3) Uani 1 1 d . . . H2A H 0.1426 0.5148 0.3261 0.022 Uiso 1 1 calc R . . H2B H 0.0954 0.4966 0.1380 0.022 Uiso 1 1 calc R . . C22 C -0.37922(14) 0.58467(6) 0.03490(16) 0.0228(3) Uani 1 1 d . . . H22 H -0.3453 0.5661 -0.0630 0.027 Uiso 1 1 calc R . . C5 C -0.15102(14) 0.42901(5) 0.11946(15) 0.0200(3) Uani 1 1 d . . . H5A H -0.2056 0.4062 0.2012 0.024 Uiso 1 1 calc R . . H5B H -0.0460 0.4212 0.1383 0.024 Uiso 1 1 calc R . . C8 C 0.04160(14) 0.67590(5) 0.28216(15) 0.0194(3) Uani 1 1 d . . . C7 C 0.09397(14) 0.61774(5) 0.32345(15) 0.0206(3) Uani 1 1 d . . . H7A H 0.1978 0.6193 0.3593 0.025 Uiso 1 1 calc R . . H7B H 0.0378 0.6029 0.4191 0.025 Uiso 1 1 calc R . . N15 N -0.17908(14) 0.88041(5) 0.16107(15) 0.0340(3) Uani 1 1 d . . . C17 C -0.37743(14) 0.55659(6) 0.18981(16) 0.0207(3) Uani 1 1 d . . . C6 C 0.19388(14) 0.58969(5) 0.05864(15) 0.0187(3) Uani 1 1 d . . . H6A H 0.2825 0.5692 0.0961 0.022 Uiso 1 1 calc R . . H6B H 0.2177 0.6301 0.0571 0.022 Uiso 1 1 calc R . . C11 C -0.06749(15) 0.78251(6) 0.21611(16) 0.0217(3) Uani 1 1 d . . . C21 C -0.42934(14) 0.63887(6) 0.02197(16) 0.0246(3) Uani 1 1 d . . . H21 H -0.4323 0.6573 -0.0845 0.029 Uiso 1 1 calc R . . C14 C -0.12842(15) 0.83721(6) 0.18457(16) 0.0258(3) Uani 1 1 d . . . C19 C -0.47087(15) 0.63977(6) 0.32233(17) 0.0256(3) Uani 1 1 d . . . H19 H -0.5004 0.6589 0.4212 0.031 Uiso 1 1 calc R . . C16 C -0.33011(14) 0.49649(6) 0.19890(16) 0.0227(3) Uani 1 1 d . . . H16A H -0.3451 0.4824 0.3149 0.027 Uiso 1 1 calc R . . H16B H -0.3923 0.4741 0.1209 0.027 Uiso 1 1 calc R . . C9 C 0.11767(15) 0.72305(6) 0.33451(16) 0.0233(3) Uani 1 1 d . . . H9 H 0.2079 0.7189 0.3939 0.028 Uiso 1 1 calc R . . C20 C -0.47566(14) 0.66645(6) 0.16628(17) 0.0242(3) Uani 1 1 d . . . C3 C -0.08079(14) 0.50663(5) 0.29462(14) 0.0196(3) Uani 1 1 d . . . H3A H -0.0729 0.4764 0.3798 0.024 Uiso 1 1 calc R . . H3B H -0.1236 0.5398 0.3499 0.024 Uiso 1 1 calc R . . C13 C -0.08926(15) 0.68295(6) 0.19343(17) 0.0258(3) Uani 1 1 d . . . H13 H -0.1419 0.6510 0.1551 0.031 Uiso 1 1 calc R . . N24 N -0.56111(14) 0.76937(6) 0.14836(17) 0.0394(3) Uani 1 1 d . . . C18 C -0.42269(14) 0.58507(6) 0.33204(16) 0.0235(3) Uani 1 1 d . . . H18 H -0.4205 0.5666 0.4384 0.028 Uiso 1 1 calc R . . C12 C -0.14356(15) 0.73557(6) 0.16041(18) 0.0270(3) Uani 1 1 d . . . H12 H -0.2331 0.7398 0.0995 0.032 Uiso 1 1 calc R . . C23 C -0.52454(15) 0.72362(6) 0.15576(18) 0.0291(3) Uani 1 1 d . . . C10 C 0.06438(16) 0.77602(6) 0.30171(17) 0.0265(3) Uani 1 1 d . . . H10 H 0.1181 0.8080 0.3378 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0219(6) 0.0153(6) 0.0158(5) -0.0029(4) 0.0017(4) -0.0020(4) N4 0.0199(6) 0.0170(6) 0.0181(5) -0.0034(4) 0.0006(4) -0.0016(4) C2 0.0216(7) 0.0170(7) 0.0174(5) 0.0002(5) -0.0016(5) -0.0004(5) C22 0.0182(7) 0.0282(8) 0.0220(6) -0.0053(6) 0.0011(5) -0.0039(6) C5 0.0244(7) 0.0175(7) 0.0180(6) 0.0001(5) 0.0011(5) -0.0012(5) C8 0.0209(7) 0.0196(7) 0.0180(6) -0.0043(5) 0.0044(5) -0.0018(5) C7 0.0219(7) 0.0205(7) 0.0194(6) -0.0033(5) -0.0015(5) -0.0011(5) N15 0.0403(8) 0.0252(7) 0.0364(7) -0.0008(6) -0.0007(6) 0.0005(6) C17 0.0149(6) 0.0227(7) 0.0246(6) -0.0032(5) -0.0001(5) -0.0039(5) C6 0.0192(6) 0.0169(6) 0.0200(6) -0.0018(5) 0.0004(5) -0.0022(5) C11 0.0250(7) 0.0192(7) 0.0212(6) -0.0012(5) 0.0061(5) -0.0014(5) C21 0.0194(7) 0.0289(8) 0.0253(6) 0.0029(6) -0.0008(5) -0.0048(6) C14 0.0278(8) 0.0238(8) 0.0259(7) -0.0024(6) 0.0041(6) -0.0041(6) C19 0.0247(7) 0.0254(8) 0.0268(7) -0.0054(6) 0.0037(5) 0.0002(6) C16 0.0210(7) 0.0225(7) 0.0249(6) -0.0023(5) 0.0035(5) -0.0030(5) C9 0.0229(7) 0.0240(8) 0.0229(6) -0.0037(5) -0.0012(5) -0.0029(6) C20 0.0177(7) 0.0225(7) 0.0324(7) -0.0008(6) 0.0010(5) -0.0023(5) C3 0.0238(7) 0.0198(7) 0.0153(6) -0.0013(5) 0.0009(5) -0.0023(5) C13 0.0228(7) 0.0189(7) 0.0357(7) -0.0043(6) -0.0016(6) -0.0038(5) N24 0.0358(8) 0.0313(8) 0.0514(8) 0.0079(6) 0.0118(6) 0.0044(6) C18 0.0239(7) 0.0250(8) 0.0218(6) -0.0007(5) 0.0013(5) 0.0000(6) C12 0.0202(7) 0.0256(8) 0.0352(7) -0.0015(6) -0.0022(6) -0.0016(6) C23 0.0220(7) 0.0292(9) 0.0364(8) 0.0029(7) 0.0059(6) -0.0008(6) C10 0.0314(8) 0.0207(7) 0.0275(7) -0.0051(6) -0.0002(6) -0.0060(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.4653(15) . ? N1 C7 1.4603(15) . ? N1 C6 1.4611(16) . ? N4 C5 1.4671(16) . ? N4 C16 1.4605(16) . ? N4 C3 1.4687(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5189(18) . ? C22 H22 0.9500 . ? C22 C17 1.3968(18) . ? C22 C21 1.3768(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.5227(16) 3_565 ? C8 C7 1.5035(18) . ? C8 C9 1.3840(17) . ? C8 C13 1.3897(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N15 C14 1.1452(18) . ? C17 C16 1.5009(18) . ? C17 C18 1.3853(18) . ? C6 C5 1.5227(16) 3_565 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 C14 1.4407(19) . ? C11 C12 1.3879(19) . ? C11 C10 1.3843(19) . ? C21 H21 0.9500 . ? C21 C20 1.3917(19) . ? C19 H19 0.9500 . ? C19 C20 1.3893(19) . ? C19 C18 1.3806(19) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C9 H9 0.9500 . ? C9 C10 1.3788(19) . ? C20 C23 1.439(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C13 H13 0.9500 . ? C13 C12 1.3750(19) . ? N24 C23 1.1441(18) . ? C18 H18 0.9500 . ? C12 H12 0.9500 . ? C10 H10 0.9500 . ? 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 C7 N1 C2 111.53(9) . . ? C7 N1 C6 110.36(10) . . ? C6 N1 C2 112.62(10) . . ? C5 N4 C3 109.35(9) . . ? C16 N4 C5 109.73(10) . . ? C16 N4 C3 110.64(10) . . ? N1 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? N1 C2 C3 111.25(10) . . ? H2A C2 H2B 108.0 . . ? C3 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C17 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C21 C22 C17 120.97(12) . . ? N4 C5 H5A 108.5 . . ? N4 C5 H5B 108.5 . . ? N4 C5 C6 114.92(10) . 3_565 ? H5A C5 H5B 107.5 . . ? C6 C5 H5A 108.5 3_565 . ? C6 C5 H5B 108.5 3_565 . ? C9 C8 C7 121.95(11) . . ? C9 C8 C13 118.61(12) . . ? C13 C8 C7 119.42(11) . . ? N1 C7 C8 112.08(10) . . ? N1 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C22 C17 C16 119.97(12) . . ? C18 C17 C22 118.59(13) . . ? C18 C17 C16 121.43(12) . . ? N1 C6 C5 112.31(10) . 3_565 ? N1 C6 H6A 109.1 . . ? N1 C6 H6B 109.1 . . ? C5 C6 H6A 109.1 3_565 . ? C5 C6 H6B 109.1 3_565 . ? H6A C6 H6B 107.9 . . ? C12 C11 C14 119.08(12) . . ? C10 C11 C14 121.28(12) . . ? C10 C11 C12 119.64(12) . . ? C22 C21 H21 120.3 . . ? C22 C21 C20 119.40(12) . . ? C20 C21 H21 120.3 . . ? N15 C14 C11 178.75(16) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C18 C19 C20 119.21(12) . . ? N4 C16 C17 113.15(11) . . ? N4 C16 H16A 108.9 . . ? N4 C16 H16B 108.9 . . ? C17 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.8 . . ? C8 C9 H9 119.5 . . ? C10 C9 C8 120.98(12) . . ? C10 C9 H9 119.5 . . ? C21 C20 C23 120.09(12) . . ? C19 C20 C21 120.47(13) . . ? C19 C20 C23 119.41(13) . . ? N4 C3 C2 111.95(10) . . ? N4 C3 H3A 109.2 . . ? N4 C3 H3B 109.2 . . ? C2 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C8 C13 H13 119.6 . . ? C12 C13 C8 120.88(12) . . ? C12 C13 H13 119.6 . . ? C17 C18 H18 119.3 . . ? C19 C18 C17 121.32(12) . . ? C19 C18 H18 119.3 . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 119.96(13) . . ? C13 C12 H12 120.0 . . ? N24 C23 C20 178.83(16) . . ? C11 C10 H10 120.0 . . ? C9 C10 C11 119.90(12) . . ? C9 C10 H10 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 N4 87.33(12) . . . . ? C2 N1 C7 C8 -156.50(10) . . . . ? C2 N1 C6 C5 78.68(12) . . . 3_565 ? C22 C17 C16 N4 64.36(15) . . . . ? C22 C17 C18 C19 0.96(19) . . . . ? C22 C21 C20 C19 0.3(2) . . . . ? C22 C21 C20 C23 178.27(12) . . . . ? C5 N4 C16 C17 -163.80(10) . . . . ? C5 N4 C3 C2 82.17(12) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C8 C13 C12 C11 -0.1(2) . . . . ? C7 N1 C2 C3 79.36(12) . . . . ? C7 N1 C6 C5 -155.96(10) . . . 3_565 ? C7 C8 C9 C10 -177.09(12) . . . . ? C7 C8 C13 C12 176.99(12) . . . . ? C17 C22 C21 C20 1.52(19) . . . . ? C6 N1 C2 C3 -155.92(9) . . . . ? C6 N1 C7 C8 77.51(13) . . . . ? C21 C22 C17 C16 176.60(12) . . . . ? C21 C22 C17 C18 -2.14(19) . . . . ? C21 C20 C23 N24 -99(8) . . . . ? C14 C11 C12 C13 -178.17(13) . . . . ? C14 C11 C10 C9 178.00(12) . . . . ? C19 C20 C23 N24 79(8) . . . . ? C16 N4 C5 C6 82.14(13) . . . 3_565 ? C16 N4 C3 C2 -156.86(11) . . . . ? C16 C17 C18 C19 -177.77(12) . . . . ? C9 C8 C7 N1 -137.61(12) . . . . ? C9 C8 C13 C12 -1.0(2) . . . . ? C20 C19 C18 C17 0.8(2) . . . . ? C3 N4 C5 C6 -156.34(10) . . . 3_565 ? C3 N4 C16 C17 75.46(13) . . . . ? C13 C8 C7 N1 44.45(16) . . . . ? C13 C8 C9 C10 0.9(2) . . . . ? C18 C17 C16 N4 -116.93(13) . . . . ? C18 C19 C20 C21 -1.5(2) . . . . ? C18 C19 C20 C23 -179.44(13) . . . . ? C12 C11 C14 N15 58(7) . . . . ? C12 C11 C10 C9 -1.5(2) . . . . ? C10 C11 C14 N15 -122(7) . . . . ? C10 C11 C12 C13 1.3(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967728' ####################################################################### # # 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_L2 _audit_creation_date 2013-08-29 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(Cl), C40 H46 N4 O8, 2(H2 O)' _chemical_formula_sum 'C40 H50 Cl2 N4 O10' _chemical_formula_weight 817.74 _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 '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' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.933(4) _cell_length_b 8.7190(17) _cell_length_c 20.640(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.83(3) _cell_angle_gamma 90.00 _cell_volume 3863.1(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_process_details 'Multi-scan routine within XDS' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1728 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1045 _diffrn_reflns_av_unetI/netI 0.0831 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 16180 _diffrn_reflns_theta_full 27.13 _diffrn_reflns_theta_max 27.13 _diffrn_reflns_theta_min 1.90 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'Phi Scan' _diffrn_radiation_monochromator 'Silicon Double Crystal' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.71080 _diffrn_source 'sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3945 _reflns_number_total 4217 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_collection 'BluIce (McPhillips, 2002)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_diff_density_max 0.464 _refine_diff_density_min -0.654 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4217 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0532 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+4.5730P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1346 _refine_ls_wR_factor_ref 0.1374 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, H1 of O28, All C(H,H) groups At 1.5 times of: All O(H,H) groups, H26 of O26, H16 of O16 2. Restrained distances H26-O26 0.82 with sigma of 0.02 H16-O16 0.82 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(O28) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005 4.a Free rotating group: O28(H1,H28A,H28B) 4.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C17(H17A,H17B) 4.c Aromatic/amide H refined with riding coordinates: C12(H12), C10(H10), C9(H9), C20(H20), C19(H19), C13(H13), C22(H22), C23(H23) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl27 Cl 0.487624(17) 0.20485(4) 0.033079(18) 0.01679(14) Uani 1 1 d . . . O25 O 0.40240(6) 0.54989(14) 0.22224(6) 0.0226(3) Uani 1 1 d . . . O26 O 0.40134(5) 0.53597(14) 0.33037(6) 0.0206(3) Uani 1 1 d D . . H26 H 0.4397(8) 0.511(3) 0.3334(12) 0.031 Uiso 1 1 d D . . O15 O 0.34429(6) 0.65919(16) 0.58303(6) 0.0224(3) Uani 1 1 d . . . O16 O 0.37042(6) 0.60490(17) 0.48586(6) 0.0256(3) Uani 1 1 d D . . H16 H 0.4030(10) 0.655(3) 0.5041(13) 0.038 Uiso 1 1 d D . . N4 N 0.07130(6) 0.52985(14) 0.21934(6) 0.0124(3) Uani 1 1 d . . . N1 N 0.04648(6) 0.42339(14) 0.38700(6) 0.0123(3) Uani 1 1 d . . . C24 C 0.37456(7) 0.55604(17) 0.26775(8) 0.0163(3) Uani 1 1 d . . . C2 C 0.06862(7) 0.52615(17) 0.33732(7) 0.0127(3) Uani 1 1 d . . . H2A H 0.1051 0.5857 0.3604 0.015 Uiso 1 1 calc R . . H2B H 0.0351 0.5999 0.3192 0.015 Uiso 1 1 calc R . . C12 C 0.26606(7) 0.42524(18) 0.44654(8) 0.0162(3) Uani 1 1 d . . . H12 H 0.3010 0.4040 0.4274 0.019 Uiso 1 1 calc R . . C3 C 0.08670(7) 0.43821(17) 0.27988(7) 0.0126(3) Uani 1 1 d . . . H3A H 0.1319 0.4159 0.2903 0.015 Uiso 1 1 calc R . . H3B H 0.0640 0.3394 0.2734 0.015 Uiso 1 1 calc R . . C5 C 0.07028(7) 0.43930(18) 0.15931(7) 0.0137(3) Uani 1 1 d . . . H5A H 0.1080 0.3742 0.1662 0.016 Uiso 1 1 calc R . . H5B H 0.0721 0.5101 0.1223 0.016 Uiso 1 1 calc R . . C14 C 0.33226(7) 0.60285(19) 0.52798(8) 0.0162(3) Uani 1 1 d . . . C10 C 0.22018(7) 0.55528(18) 0.52795(7) 0.0159(3) Uani 1 1 d . . . H10 H 0.2242 0.6224 0.5648 0.019 Uiso 1 1 calc R . . C11 C 0.27175(7) 0.52554(18) 0.50001(7) 0.0147(3) Uani 1 1 d . . . C6 C -0.01307(7) 0.33687(18) 0.36043(7) 0.0133(3) Uani 1 1 d . . . H6A H -0.0205 0.2635 0.3946 0.016 Uiso 1 1 calc R . . H6B H -0.0077 0.2768 0.3213 0.016 Uiso 1 1 calc R . . C9 C 0.16293(7) 0.48726(19) 0.50210(7) 0.0156(3) Uani 1 1 d . . . H9 H 0.1279 0.5088 0.5210 0.019 Uiso 1 1 calc R . . C8 C 0.15709(7) 0.38740(17) 0.44837(7) 0.0139(3) Uani 1 1 d . . . C20 C 0.27916(8) 0.63525(18) 0.30920(8) 0.0170(3) Uani 1 1 d . . . H20 H 0.3038 0.6468 0.3525 0.020 Uiso 1 1 calc R . . C19 C 0.21566(7) 0.66489(19) 0.29729(8) 0.0172(3) Uani 1 1 d . . . H19 H 0.1971 0.6978 0.3327 0.021 Uiso 1 1 calc R . . C7 C 0.09579(7) 0.31073(17) 0.42001(7) 0.0146(3) Uani 1 1 d . . . H7A H 0.0807 0.2570 0.4560 0.018 Uiso 1 1 calc R . . H7B H 0.1023 0.2329 0.3872 0.018 Uiso 1 1 calc R . . C13 C 0.20900(7) 0.35641(18) 0.42129(8) 0.0162(3) Uani 1 1 d . . . H13 H 0.2053 0.2873 0.3851 0.019 Uiso 1 1 calc R . . C21 C 0.30666(7) 0.58833(17) 0.25725(8) 0.0149(3) Uani 1 1 d . . . C22 C 0.27039(7) 0.57054(18) 0.19396(8) 0.0161(3) Uani 1 1 d . . . H22 H 0.2890 0.5376 0.1587 0.019 Uiso 1 1 calc R . . C23 C 0.20711(7) 0.60085(19) 0.18243(8) 0.0163(3) Uani 1 1 d . . . H23 H 0.1827 0.5902 0.1390 0.020 Uiso 1 1 calc R . . C18 C 0.17867(7) 0.64713(17) 0.23417(8) 0.0146(3) Uani 1 1 d . . . C17 C 0.10881(7) 0.67111(18) 0.22207(8) 0.0149(3) Uani 1 1 d . . . H17A H 0.0994 0.7374 0.2577 0.018 Uiso 1 1 calc R . . H17B H 0.0956 0.7269 0.1797 0.018 Uiso 1 1 calc R . . O28 O 0.48571(7) 0.4471(2) 0.14695(9) 0.0484(5) Uani 1 1 d GU . . H1 H 0.0362 0.4923 0.4191 0.058 Uiso 1 1 d G . . H28A H 0.4580 0.4463 0.1704 0.073 Uiso 1 1 d G . . H28B H 0.4769 0.3799 0.1167 0.073 Uiso 1 1 d G . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl27 0.0175(2) 0.0179(2) 0.0159(2) 0.00220(13) 0.00556(15) 0.00187(12) O25 0.0197(6) 0.0242(6) 0.0267(7) 0.0008(5) 0.0114(5) 0.0012(5) O26 0.0146(6) 0.0241(6) 0.0219(6) -0.0003(5) 0.0007(4) 0.0006(4) O15 0.0209(6) 0.0303(6) 0.0152(6) -0.0054(5) 0.0020(4) -0.0053(5) O16 0.0178(6) 0.0401(7) 0.0199(6) -0.0090(6) 0.0064(5) -0.0100(5) N4 0.0124(6) 0.0132(6) 0.0115(6) 0.0013(5) 0.0020(4) -0.0006(5) N1 0.0113(6) 0.0142(6) 0.0110(6) 0.0004(5) 0.0013(5) -0.0007(5) C24 0.0169(7) 0.0103(6) 0.0222(8) -0.0007(6) 0.0052(6) -0.0021(5) C2 0.0130(7) 0.0135(7) 0.0115(6) 0.0012(5) 0.0025(5) -0.0015(5) C12 0.0148(7) 0.0198(7) 0.0141(7) -0.0005(6) 0.0034(5) 0.0027(6) C3 0.0136(7) 0.0129(6) 0.0114(7) 0.0011(5) 0.0027(5) -0.0002(5) C5 0.0111(7) 0.0179(7) 0.0122(7) 0.0004(5) 0.0029(5) 0.0010(5) C14 0.0155(7) 0.0190(7) 0.0138(7) 0.0011(6) 0.0019(5) 0.0010(6) C10 0.0166(7) 0.0192(7) 0.0110(7) -0.0012(6) 0.0008(5) 0.0008(6) C11 0.0141(7) 0.0172(7) 0.0114(7) 0.0015(6) -0.0004(5) 0.0007(5) C6 0.0124(7) 0.0148(6) 0.0122(7) 0.0000(6) 0.0016(5) -0.0027(5) C9 0.0143(7) 0.0209(7) 0.0116(7) 0.0015(6) 0.0027(5) 0.0022(6) C8 0.0136(7) 0.0161(7) 0.0107(7) 0.0028(6) -0.0008(5) 0.0010(5) C20 0.0177(7) 0.0182(7) 0.0152(7) -0.0033(6) 0.0031(6) -0.0044(6) C19 0.0170(7) 0.0183(7) 0.0180(8) -0.0044(6) 0.0074(6) -0.0041(6) C7 0.0137(7) 0.0158(7) 0.0134(7) 0.0019(5) 0.0007(5) -0.0002(5) C13 0.0161(7) 0.0182(7) 0.0133(7) -0.0024(6) 0.0010(5) 0.0026(6) C21 0.0142(7) 0.0124(6) 0.0191(7) 0.0003(6) 0.0059(6) -0.0024(5) C22 0.0178(7) 0.0161(7) 0.0163(7) -0.0001(6) 0.0078(6) -0.0021(6) C23 0.0160(7) 0.0191(7) 0.0139(7) 0.0005(6) 0.0038(5) -0.0034(6) C18 0.0161(7) 0.0110(7) 0.0176(7) 0.0007(5) 0.0056(6) -0.0033(5) C17 0.0147(7) 0.0121(6) 0.0183(7) 0.0024(6) 0.0043(6) 0.0000(5) O28 0.0197(7) 0.0639(11) 0.0648(11) -0.0470(9) 0.0160(7) -0.0127(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O25 C24 1.222(2) . ? O26 H26 0.858(16) . ? O26 C24 1.317(2) . ? O15 C14 1.216(2) . ? O16 H16 0.856(17) . ? O16 C14 1.325(2) . ? N4 C3 1.4631(18) . ? N4 C5 1.4655(19) . ? N4 C17 1.4757(19) . ? N1 C2 1.5146(18) . ? N1 C6 1.5106(19) . ? N1 C7 1.5154(19) . ? N1 H1 0.9546 . ? C24 C21 1.487(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.531(2) . ? C12 H12 0.9500 . ? C12 C11 1.393(2) . ? C12 C13 1.389(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.526(2) 2 ? C14 C11 1.495(2) . ? C10 H10 0.9500 . ? C10 C11 1.395(2) . ? C10 C9 1.392(2) . ? C6 C5 1.526(2) 2 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C9 H9 0.9500 . ? C9 C8 1.395(2) . ? C8 C7 1.508(2) . ? C8 C13 1.394(2) . ? C20 H20 0.9500 . ? C20 C19 1.388(2) . ? C20 C21 1.395(2) . ? C19 H19 0.9500 . ? C19 C18 1.395(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C13 H13 0.9500 . ? C21 C22 1.392(2) . ? C22 H22 0.9500 . ? C22 C23 1.385(2) . ? C23 H23 0.9500 . ? C23 C18 1.402(2) . ? C18 C17 1.516(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? O28 H28A 0.8506 . ? O28 H28B 0.8498 . ? 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 C24 O26 H26 109.8(16) . . ? C14 O16 H16 107.6(18) . . ? C3 N4 C5 112.87(12) . . ? C3 N4 C17 113.19(12) . . ? C5 N4 C17 113.19(12) . . ? C2 N1 C7 112.92(11) . . ? C2 N1 H1 104.5 . . ? C6 N1 C2 115.02(11) . . ? C6 N1 C7 108.89(11) . . ? C6 N1 H1 104.9 . . ? C7 N1 H1 110.2 . . ? O25 C24 O26 123.78(15) . . ? O25 C24 C21 122.65(15) . . ? O26 C24 C21 113.57(14) . . ? N1 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 . . ? N1 C2 C3 113.45(12) . . ? H2A C2 H2B 107.7 . . ? C3 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C13 C12 C11 119.71(14) . . ? N4 C3 C2 109.68(12) . . ? N4 C3 H3A 109.7 . . ? N4 C3 H3B 109.7 . . ? C2 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? N4 C5 H5A 108.7 . . ? N4 C5 H5B 108.7 . . ? N4 C5 C6 114.22(12) . 2 ? H5A C5 H5B 107.6 . . ? C6 C5 H5A 108.7 2 . ? C6 C5 H5B 108.7 2 . ? O15 C14 O16 124.23(15) . . ? O15 C14 C11 123.26(15) . . ? O16 C14 C11 112.51(13) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C9 C10 C11 120.41(14) . . ? C12 C11 C14 121.14(14) . . ? C12 C11 C10 119.70(14) . . ? C10 C11 C14 119.16(14) . . ? N1 C6 C5 114.03(12) . 2 ? N1 C6 H6A 108.7 . . ? N1 C6 H6B 108.7 . . ? C5 C6 H6A 108.7 2 . ? C5 C6 H6B 108.7 2 . ? H6A C6 H6B 107.6 . . ? C10 C9 H9 120.0 . . ? C10 C9 C8 119.94(14) . . ? C8 C9 H9 120.0 . . ? C9 C8 C7 120.95(14) . . ? C13 C8 C9 119.37(14) . . ? C13 C8 C7 119.67(14) . . ? C19 C20 H20 120.2 . . ? C19 C20 C21 119.64(15) . . ? C21 C20 H20 120.2 . . ? C20 C19 H19 119.5 . . ? C20 C19 C18 121.00(15) . . ? C18 C19 H19 119.5 . . ? N1 C7 H7A 109.1 . . ? N1 C7 H7B 109.1 . . ? C8 C7 N1 112.61(12) . . ? C8 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C12 C13 C8 120.85(14) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C20 C21 C24 121.42(15) . . ? C22 C21 C24 118.57(14) . . ? C22 C21 C20 120.01(14) . . ? C21 C22 H22 120.0 . . ? C23 C22 C21 119.99(14) . . ? C23 C22 H22 120.0 . . ? C22 C23 H23 119.6 . . ? C22 C23 C18 120.72(15) . . ? C18 C23 H23 119.6 . . ? C19 C18 C23 118.62(14) . . ? C19 C18 C17 120.88(14) . . ? C23 C18 C17 120.46(14) . . ? N4 C17 C18 115.34(12) . . ? N4 C17 H17A 108.4 . . ? N4 C17 H17B 108.4 . . ? C18 C17 H17A 108.4 . . ? C18 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? H28A O28 H28B 109.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O25 C24 C21 C20 -162.54(15) . . . . ? O25 C24 C21 C22 17.6(2) . . . . ? O26 C24 C21 C20 17.1(2) . . . . ? O26 C24 C21 C22 -162.81(14) . . . . ? O15 C14 C11 C12 -161.04(16) . . . . ? O15 C14 C11 C10 19.2(2) . . . . ? O16 C14 C11 C12 20.0(2) . . . . ? O16 C14 C11 C10 -159.77(14) . . . . ? N1 C2 C3 N4 146.13(12) . . . . ? C24 C21 C22 C23 -179.49(14) . . . . ? C2 N1 C6 C5 -65.82(16) . . . 2 ? C2 N1 C7 C8 51.16(16) . . . . ? C3 N4 C5 C6 74.98(16) . . . 2 ? C3 N4 C17 C18 58.58(17) . . . . ? C5 N4 C3 C2 -163.59(12) . . . . ? C5 N4 C17 C18 -71.48(16) . . . . ? C10 C9 C8 C7 179.23(14) . . . . ? C10 C9 C8 C13 0.2(2) . . . . ? C11 C12 C13 C8 0.6(2) . . . . ? C11 C10 C9 C8 0.7(2) . . . . ? C6 N1 C2 C3 -64.53(16) . . . . ? C6 N1 C7 C8 -179.79(12) . . . . ? C9 C10 C11 C12 -1.0(2) . . . . ? C9 C10 C11 C14 178.74(14) . . . . ? C9 C8 C7 N1 67.40(18) . . . . ? C9 C8 C13 C12 -0.9(2) . . . . ? C20 C19 C18 C23 -1.0(2) . . . . ? C20 C19 C18 C17 176.61(14) . . . . ? C20 C21 C22 C23 0.6(2) . . . . ? C19 C20 C21 C24 179.72(14) . . . . ? C19 C20 C21 C22 -0.4(2) . . . . ? C19 C18 C17 N4 -99.02(17) . . . . ? C7 N1 C2 C3 61.30(15) . . . . ? C7 N1 C6 C5 166.30(12) . . . 2 ? C7 C8 C13 C12 -179.88(14) . . . . ? C13 C12 C11 C14 -179.37(14) . . . . ? C13 C12 C11 C10 0.4(2) . . . . ? C13 C8 C7 N1 -113.62(15) . . . . ? C21 C20 C19 C18 0.6(2) . . . . ? C21 C22 C23 C18 -1.0(2) . . . . ? C22 C23 C18 C19 1.2(2) . . . . ? C22 C23 C18 C17 -176.40(14) . . . . ? C23 C18 C17 N4 78.55(18) . . . . ? C17 N4 C3 C2 66.19(15) . . . . ? C17 N4 C5 C6 -154.80(12) . . . 2 ? _database_code_depnum_ccdc_archive 'CCDC 967729' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_date 2013-08-27 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C80 H80 Ag2 N16, 2(Cl O4)' _chemical_formula_sum 'C80 H80 Ag2 Cl2 N16 O8' _chemical_formula_weight 1680.24 _chemical_melting_point ? 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' Ag Ag -0.8750 1.0960 '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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3620(19) _cell_length_b 15.871(3) _cell_length_c 25.586(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.64(3) _cell_angle_gamma 90.00 _cell_volume 3776.2(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.658 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_process_details 'XScale within XDS' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1728 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_special_details ; Crystal was manually re-oriented between two phi scans ; _diffrn_reflns_av_R_equivalents 0.0898 _diffrn_reflns_av_unetI/netI 0.0300 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 145774 _diffrn_reflns_theta_full 28.50 _diffrn_reflns_theta_max 29.63 _diffrn_reflns_theta_min 1.51 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method '2x Phi Scans' _diffrn_radiation_monochromator 'Silicon Double Crystal' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.71080 _diffrn_source 'Australian Synchrotron' _diffrn_standards_number 0 _reflns_number_gt 9124 _reflns_number_total 10609 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_collection 'BluIce (McPhillips, 2002)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_diff_density_max 1.374 _refine_diff_density_min -1.206 _refine_diff_density_rms 0.087 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 10609 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0403 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+3.3565P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1088 _refine_ls_wR_factor_ref 0.1136 _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. No additional restraints or modelling procedures were required beyond standard routines. The DISP command was used to account for dispersion effects from the non-standard wavelength of 0.71080 angstroms, using Brennan and Cowan values of -0.875 and 1.096 for Ag f' and f'', respectively. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C6(H6A,H6B), C9(H9A,H9B), C4(H4A,H4B), C14(H14A,H14B), C7(H7A, H7B), C3(H3A,H3B), C32(H32A,H32B), C23(H23A,H23B), C13(H13A,H13B), C10(H10A, H10B), C41(H41A,H41B) 2.b Aromatic/amide H refined with riding coordinates: C20(H20), C16(H16), C19(H19), C38(H38), C35(H35), C29(H29), C28(H28), C25(H25), C26(H26), C34(H34), C17(H17), C37(H37), C47(H47), C46(H46), C43(H43), C44(H44) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ag1 Ag 0.743290(17) 0.592475(9) 0.151703(6) 0.02340(6) Uani 1 1 d . . . N2 N 0.6477(2) 0.74157(11) 0.15137(7) 0.0253(4) Uani 1 1 d . . . N5 N 0.6839(2) 0.62110(12) 0.24330(7) 0.0258(4) Uani 1 1 d . . . C24 C 0.4996(3) 0.57912(13) 0.30245(9) 0.0272(4) Uani 1 1 d . . . C12 C 0.8729(3) 0.76076(14) 0.10819(9) 0.0291(4) Uani 1 1 d . . . H12A H 0.8123 0.7635 0.0738 0.035 Uiso 1 1 calc R . . H12B H 0.9534 0.8009 0.1070 0.035 Uiso 1 1 calc R . . N11 N 0.9325(2) 0.67429(12) 0.11562(7) 0.0263(4) Uani 1 1 d . . . C6 C 0.8055(3) 0.58885(15) 0.27959(9) 0.0310(5) Uani 1 1 d . . . H6A H 0.7912 0.5279 0.2855 0.037 Uiso 1 1 calc R . . H6B H 0.8070 0.6179 0.3139 0.037 Uiso 1 1 calc R . . N8 N 0.9594(2) 0.55546(12) 0.20879(8) 0.0287(4) Uani 1 1 d . . . C9 C 1.0808(3) 0.58640(15) 0.18237(10) 0.0314(5) Uani 1 1 d . . . H9A H 1.0995 0.5458 0.1546 0.038 Uiso 1 1 calc R . . H9B H 1.1678 0.5886 0.2083 0.038 Uiso 1 1 calc R . . C27 C 0.4368(3) 0.59516(14) 0.40574(9) 0.0287(4) Uani 1 1 d . . . C4 C 0.6697(3) 0.71301(13) 0.24878(9) 0.0281(4) Uani 1 1 d . . . H4A H 0.7669 0.7383 0.2544 0.034 Uiso 1 1 calc R . . H4B H 0.6211 0.7250 0.2803 0.034 Uiso 1 1 calc R . . C20 C 0.4058(3) 0.89292(15) 0.12529(10) 0.0298(4) Uani 1 1 d . . . H20 H 0.3500 0.8601 0.1465 0.036 Uiso 1 1 calc R . . C33 C 0.9195(3) 0.40923(14) 0.17411(10) 0.0293(5) Uani 1 1 d . . . C14 C 0.5422(3) 0.76038(13) 0.10512(9) 0.0280(4) Uani 1 1 d . . . H14A H 0.4519 0.7296 0.1088 0.034 Uiso 1 1 calc R . . H14B H 0.5803 0.7392 0.0731 0.034 Uiso 1 1 calc R . . C16 C 0.5868(3) 0.90213(15) 0.06628(10) 0.0319(5) Uani 1 1 d . . . H16 H 0.6541 0.8754 0.0467 0.038 Uiso 1 1 calc R . . C7 C 0.9498(3) 0.60179(16) 0.25866(9) 0.0321(5) Uani 1 1 d . . . H7A H 0.9641 0.6627 0.2527 0.039 Uiso 1 1 calc R . . H7B H 1.0277 0.5825 0.2854 0.039 Uiso 1 1 calc R . . C3 C 0.5852(3) 0.75486(14) 0.20113(9) 0.0290(4) Uani 1 1 d . . . H3A H 0.4858 0.7326 0.1971 0.035 Uiso 1 1 calc R . . H3B H 0.5800 0.8162 0.2078 0.035 Uiso 1 1 calc R . . C19 C 0.3847(3) 0.97938(15) 0.12171(10) 0.0304(4) Uani 1 1 d . . . H19 H 0.3151 1.0059 0.1404 0.036 Uiso 1 1 calc R . . C30 C 0.4089(3) 0.60485(16) 0.45954(10) 0.0339(5) Uani 1 1 d . . . C38 C 1.0074(3) 0.37786(15) 0.13810(10) 0.0310(5) Uani 1 1 d . . . H38 H 1.1073 0.3903 0.1424 0.037 Uiso 1 1 calc R . . C32 C 0.9794(3) 0.46345(15) 0.21995(10) 0.0330(5) Uani 1 1 d . . . H32A H 0.9311 0.4486 0.2511 0.040 Uiso 1 1 calc R . . H32B H 1.0832 0.4515 0.2284 0.040 Uiso 1 1 calc R . . C15 C 0.5082(3) 0.85386(14) 0.09810(9) 0.0274(4) Uani 1 1 d . . . C23 C 0.5479(3) 0.57470(14) 0.24812(9) 0.0273(4) Uani 1 1 d . . . H23A H 0.5613 0.5148 0.2389 0.033 Uiso 1 1 calc R . . H23B H 0.4710 0.5981 0.2224 0.033 Uiso 1 1 calc R . . C13 C 0.7836(3) 0.78817(14) 0.15109(9) 0.0278(4) Uani 1 1 d . . . H13A H 0.8417 0.7808 0.1857 0.033 Uiso 1 1 calc R . . H13B H 0.7616 0.8489 0.1467 0.033 Uiso 1 1 calc R . . C35 C 0.7161(3) 0.33711(16) 0.12679(11) 0.0353(5) Uani 1 1 d . . . H35 H 0.6172 0.3222 0.1235 0.042 Uiso 1 1 calc R . . C10 C 1.0553(3) 0.67337(15) 0.15765(9) 0.0305(5) Uani 1 1 d . . . H10A H 1.0367 0.7142 0.1853 0.037 Uiso 1 1 calc R . . H10B H 1.1432 0.6916 0.1427 0.037 Uiso 1 1 calc R . . C29 C 0.4116(3) 0.64406(13) 0.31641(9) 0.0274(4) Uani 1 1 d . . . H29 H 0.3729 0.6832 0.2905 0.033 Uiso 1 1 calc R . . C36 C 0.8037(3) 0.30824(15) 0.09033(10) 0.0340(5) Uani 1 1 d . . . N22 N 0.4345(3) 1.18831(15) 0.08139(13) 0.0514(7) Uani 1 1 d . . . C28 C 0.3795(2) 0.65232(14) 0.36782(9) 0.0276(4) Uani 1 1 d . . . H28 H 0.3190 0.6967 0.3770 0.033 Uiso 1 1 calc R . . N31 N 0.3873(3) 0.61300(17) 0.50241(10) 0.0443(6) Uani 1 1 d . . . C18 C 0.4670(3) 1.02709(14) 0.09033(10) 0.0302(5) Uani 1 1 d . . . C25 C 0.5486(3) 0.51971(14) 0.34045(10) 0.0331(5) Uani 1 1 d . . . H25 H 0.6031 0.4730 0.3307 0.040 Uiso 1 1 calc R . . C26 C 0.5197(3) 0.52725(15) 0.39209(10) 0.0323(5) Uani 1 1 d . . . H26 H 0.5556 0.4869 0.4178 0.039 Uiso 1 1 calc R . . C21 C 0.4481(3) 1.11695(17) 0.08575(12) 0.0375(5) Uani 1 1 d . . . C34 C 0.7737(3) 0.38753(15) 0.16784(11) 0.0323(5) Uani 1 1 d . . . H34 H 0.7131 0.4079 0.1924 0.039 Uiso 1 1 calc R . . C17 C 0.5684(3) 0.98872(15) 0.06265(10) 0.0328(5) Uani 1 1 d . . . H17 H 0.6245 1.0214 0.0415 0.039 Uiso 1 1 calc R . . C37 C 0.9500(3) 0.32877(15) 0.09623(10) 0.0329(5) Uani 1 1 d . . . H37 H 1.0101 0.3089 0.0714 0.039 Uiso 1 1 calc R . . Cl50 Cl 0.37064(6) 0.34826(4) 0.22176(2) 0.03349(12) Uani 1 1 d . . . O51 O 0.3345(3) 0.42781(16) 0.19907(14) 0.0741(9) Uani 1 1 d . . . O53 O 0.5138(2) 0.34867(13) 0.24798(9) 0.0458(5) Uani 1 1 d . . . O54 O 0.2671(3) 0.31772(19) 0.25335(11) 0.0639(7) Uani 1 1 d . . . O52 O 0.3692(4) 0.2900(2) 0.17740(12) 0.0805(9) Uani 1 1 d . . . C39 C 0.7479(4) 0.2588(2) 0.04519(13) 0.0476(7) Uani 1 1 d . . . N40 N 0.7081(4) 0.2233(3) 0.00797(14) 0.0751(10) Uani 1 1 d . . . C42 C 0.8609(2) 0.60798(14) 0.02788(9) 0.0258(4) Uani 1 1 d . . . C41 C 0.9806(2) 0.64450(15) 0.06574(9) 0.0289(4) Uani 1 1 d . . . H41A H 1.0558 0.6011 0.0738 0.035 Uiso 1 1 calc R . . H41B H 1.0245 0.6923 0.0485 0.035 Uiso 1 1 calc R . . C47 C 0.8313(3) 0.52191(15) 0.03024(9) 0.0304(5) Uani 1 1 d . . . H47 H 0.8841 0.4883 0.0565 0.037 Uiso 1 1 calc R . . C46 C 0.7265(3) 0.48470(14) -0.00492(9) 0.0300(5) Uani 1 1 d . . . H46 H 0.7075 0.4261 -0.0030 0.036 Uiso 1 1 calc R . . C43 C 0.7815(3) 0.65670(14) -0.01035(9) 0.0283(4) Uani 1 1 d . . . H43 H 0.7995 0.7155 -0.0119 0.034 Uiso 1 1 calc R . . C44 C 0.6763(3) 0.62073(14) -0.04615(9) 0.0291(4) Uani 1 1 d . . . H44 H 0.6233 0.6544 -0.0723 0.035 Uiso 1 1 calc R . . C48 C 0.5393(3) 0.49622(14) -0.07993(9) 0.0291(4) Uani 1 1 d . . . C45 C 0.6493(2) 0.53462(14) -0.04327(9) 0.0267(4) Uani 1 1 d . . . N49 N 0.4505(2) 0.46572(13) -0.10771(9) 0.0335(4) 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 Ag1 0.03033(9) 0.01749(8) 0.02128(9) -0.00079(5) -0.00178(6) -0.00097(5) N2 0.0336(9) 0.0183(8) 0.0229(8) -0.0008(6) -0.0018(7) -0.0014(7) N5 0.0354(10) 0.0186(8) 0.0222(8) 0.0002(6) -0.0008(7) -0.0009(7) C24 0.0375(11) 0.0190(9) 0.0249(10) -0.0009(8) 0.0029(9) -0.0005(8) C12 0.0380(12) 0.0219(10) 0.0266(10) 0.0023(8) 0.0006(9) -0.0036(8) N11 0.0325(9) 0.0224(8) 0.0227(8) -0.0003(7) -0.0025(7) -0.0013(7) C6 0.0407(12) 0.0279(11) 0.0226(10) 0.0016(8) -0.0043(9) 0.0011(9) N8 0.0361(10) 0.0243(9) 0.0243(9) 0.0004(7) -0.0016(7) 0.0011(7) C9 0.0318(11) 0.0316(11) 0.0294(11) -0.0001(9) -0.0028(9) 0.0016(9) C27 0.0343(11) 0.0248(10) 0.0272(11) -0.0023(8) 0.0048(9) -0.0007(8) C4 0.0415(12) 0.0184(9) 0.0237(10) -0.0025(7) 0.0007(9) -0.0025(8) C20 0.0332(11) 0.0225(10) 0.0327(11) 0.0019(8) -0.0009(9) -0.0007(8) C33 0.0350(11) 0.0223(10) 0.0299(11) 0.0076(8) 0.0002(9) 0.0066(8) C14 0.0367(11) 0.0188(9) 0.0269(10) -0.0027(8) -0.0037(9) 0.0005(8) C16 0.0425(13) 0.0279(11) 0.0251(10) 0.0015(8) 0.0029(9) 0.0069(9) C7 0.0376(12) 0.0322(11) 0.0246(10) -0.0007(9) -0.0050(9) -0.0002(9) C3 0.0403(12) 0.0194(9) 0.0271(10) -0.0011(8) 0.0033(9) 0.0004(8) C19 0.0337(11) 0.0252(10) 0.0314(11) -0.0013(8) 0.0005(9) 0.0035(9) C30 0.0411(13) 0.0284(11) 0.0328(12) -0.0003(9) 0.0069(10) 0.0032(9) C38 0.0307(11) 0.0273(10) 0.0342(12) 0.0059(9) -0.0002(9) 0.0044(9) C32 0.0423(13) 0.0251(10) 0.0299(11) 0.0063(9) -0.0023(9) 0.0063(9) C15 0.0370(11) 0.0204(9) 0.0228(10) -0.0009(7) -0.0050(8) 0.0013(8) C23 0.0387(12) 0.0201(9) 0.0229(10) -0.0015(7) 0.0025(8) -0.0027(8) C13 0.0369(11) 0.0195(9) 0.0258(10) -0.0008(7) -0.0025(8) -0.0045(8) C35 0.0308(11) 0.0271(11) 0.0469(14) 0.0090(10) 0.0003(10) 0.0012(9) C10 0.0318(11) 0.0308(11) 0.0273(11) 0.0005(9) -0.0039(9) -0.0045(9) C29 0.0331(11) 0.0193(9) 0.0294(11) 0.0030(8) 0.0010(8) -0.0005(8) C36 0.0398(12) 0.0245(10) 0.0361(12) 0.0066(9) -0.0026(10) 0.0005(9) N22 0.0507(14) 0.0245(11) 0.082(2) 0.0050(11) 0.0182(14) 0.0027(10) C28 0.0310(10) 0.0199(9) 0.0321(11) -0.0012(8) 0.0048(8) 0.0006(8) N31 0.0595(15) 0.0424(12) 0.0318(11) -0.0029(10) 0.0090(10) 0.0096(11) C18 0.0351(11) 0.0216(10) 0.0319(11) 0.0017(8) -0.0045(9) 0.0010(8) C25 0.0482(13) 0.0212(10) 0.0312(11) 0.0034(8) 0.0099(10) 0.0094(9) C26 0.0413(12) 0.0272(11) 0.0286(11) 0.0052(9) 0.0052(9) 0.0084(9) C21 0.0374(13) 0.0278(11) 0.0473(15) 0.0025(10) 0.0054(11) 0.0011(10) C34 0.0346(11) 0.0222(10) 0.0405(13) 0.0076(9) 0.0055(10) 0.0051(9) C17 0.0402(12) 0.0278(11) 0.0302(11) 0.0074(9) 0.0028(9) 0.0014(9) C37 0.0366(12) 0.0282(11) 0.0337(12) 0.0037(9) 0.0035(9) 0.0040(9) Cl50 0.0319(3) 0.0277(3) 0.0391(3) 0.0077(2) -0.0038(2) 0.0010(2) O51 0.0446(12) 0.0454(12) 0.123(3) 0.0437(15) -0.0289(14) -0.0097(10) O53 0.0379(10) 0.0424(11) 0.0527(12) 0.0081(9) -0.0137(9) 0.0041(8) O54 0.0525(14) 0.0698(16) 0.0699(17) 0.0145(13) 0.0094(12) -0.0044(12) O52 0.089(2) 0.082(2) 0.0698(18) -0.0287(16) 0.0029(16) -0.0200(17) C39 0.0495(16) 0.0439(15) 0.0480(16) -0.0027(13) -0.0002(13) -0.0080(13) N40 0.074(2) 0.091(3) 0.0587(19) -0.0247(18) -0.0013(16) -0.025(2) C42 0.0296(10) 0.0248(10) 0.0229(9) -0.0013(8) 0.0027(8) -0.0024(8) C41 0.0297(10) 0.0306(11) 0.0255(10) -0.0014(8) -0.0004(8) -0.0042(8) C47 0.0388(12) 0.0248(10) 0.0259(10) 0.0018(8) -0.0035(9) 0.0021(9) C46 0.0396(12) 0.0197(9) 0.0294(11) 0.0016(8) -0.0015(9) -0.0003(8) C43 0.0375(11) 0.0202(9) 0.0265(10) 0.0009(8) 0.0006(9) -0.0028(8) C44 0.0386(12) 0.0213(10) 0.0259(10) 0.0020(8) -0.0031(9) -0.0001(9) C48 0.0353(11) 0.0216(9) 0.0295(11) -0.0003(8) 0.0001(9) 0.0005(8) C45 0.0313(10) 0.0224(9) 0.0256(10) -0.0025(8) -0.0010(8) -0.0017(8) N49 0.0419(11) 0.0225(9) 0.0340(10) -0.0016(8) -0.0048(9) -0.0024(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.5294(19) . ? Ag1 N5 2.512(2) . ? Ag1 N11 2.460(2) . ? Ag1 N8 2.427(2) . ? Ag1 N49 2.223(2) 3_665 ? N2 C14 1.482(3) . ? N2 C3 1.477(3) . ? N2 C13 1.472(3) . ? N5 C6 1.475(3) . ? N5 C4 1.473(3) . ? N5 C23 1.488(3) . ? C24 C23 1.512(3) . ? C24 C29 1.392(3) . ? C24 C25 1.394(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 N11 1.485(3) . ? C12 C13 1.518(3) . ? N11 C10 1.480(3) . ? N11 C41 1.479(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.523(4) . ? N8 C9 1.472(3) . ? N8 C7 1.484(3) . ? N8 C32 1.495(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.525(3) . ? C27 C30 1.439(3) . ? C27 C28 1.390(3) . ? C27 C26 1.396(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C3 1.526(3) . ? C20 H20 0.9500 . ? C20 C19 1.388(3) . ? C20 C15 1.393(3) . ? C33 C38 1.396(3) . ? C33 C32 1.510(4) . ? C33 C34 1.399(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.524(3) . ? C16 H16 0.9500 . ? C16 C15 1.389(3) . ? C16 C17 1.387(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C19 H19 0.9500 . ? C19 C18 1.398(3) . ? C30 N31 1.146(4) . ? C38 H38 0.9500 . ? C38 C37 1.382(4) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C35 H35 0.9500 . ? C35 C36 1.389(4) . ? C35 C34 1.380(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C29 H29 0.9500 . ? C29 C28 1.389(3) . ? C36 C37 1.399(4) . ? C36 C39 1.443(4) . ? N22 C21 1.144(4) . ? C28 H28 0.9500 . ? C18 C21 1.440(3) . ? C18 C17 1.389(4) . ? C25 H25 0.9500 . ? C25 C26 1.384(3) . ? C26 H26 0.9500 . ? C34 H34 0.9500 . ? C17 H17 0.9500 . ? C37 H37 0.9500 . ? Cl50 O51 1.414(2) . ? Cl50 O53 1.428(2) . ? Cl50 O54 1.417(3) . ? Cl50 O52 1.463(3) . ? C39 N40 1.132(4) . ? C42 C41 1.510(3) . ? C42 C47 1.396(3) . ? C42 C43 1.393(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C47 H47 0.9500 . ? C47 C46 1.384(3) . ? C46 H46 0.9500 . ? C46 C45 1.396(3) . ? C43 H43 0.9500 . ? C43 C44 1.388(3) . ? C44 H44 0.9500 . ? C44 C45 1.393(3) . ? C48 C45 1.445(3) . ? C48 N49 1.137(3) . ? N49 Ag1 2.223(2) 3_665 ? 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 N5 Ag1 N2 73.60(6) . . ? N11 Ag1 N2 76.98(6) . . ? N11 Ag1 N5 120.08(6) . . ? N8 Ag1 N2 119.90(6) . . ? N8 Ag1 N5 75.00(7) . . ? N8 Ag1 N11 76.54(7) . . ? N49 Ag1 N2 96.86(7) 3_665 . ? N49 Ag1 N5 106.97(8) 3_665 . ? N49 Ag1 N11 127.61(7) 3_665 . ? N49 Ag1 N8 141.19(7) 3_665 . ? C14 N2 Ag1 113.21(12) . . ? C3 N2 Ag1 107.81(13) . . ? C3 N2 C14 111.46(19) . . ? C13 N2 Ag1 99.46(13) . . ? C13 N2 C14 113.06(18) . . ? C13 N2 C3 111.18(18) . . ? C6 N5 Ag1 106.66(14) . . ? C6 N5 C23 112.43(18) . . ? C4 N5 Ag1 107.47(13) . . ? C4 N5 C6 110.82(18) . . ? C4 N5 C23 113.23(19) . . ? C23 N5 Ag1 105.76(13) . . ? C29 C24 C23 121.3(2) . . ? C29 C24 C25 118.6(2) . . ? C25 C24 C23 120.0(2) . . ? H12A C12 H12B 107.7 . . ? N11 C12 H12A 108.8 . . ? N11 C12 H12B 108.8 . . ? N11 C12 C13 113.71(18) . . ? C13 C12 H12A 108.8 . . ? C13 C12 H12B 108.8 . . ? C12 N11 Ag1 105.04(14) . . ? C10 N11 Ag1 104.74(13) . . ? C10 N11 C12 110.53(18) . . ? C41 N11 Ag1 117.35(13) . . ? C41 N11 C12 109.40(18) . . ? C41 N11 C10 109.59(18) . . ? N5 C6 H6A 109.1 . . ? N5 C6 H6B 109.1 . . ? N5 C6 C7 112.52(19) . . ? H6A C6 H6B 107.8 . . ? C7 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C9 N8 Ag1 106.07(14) . . ? C9 N8 C7 110.88(19) . . ? C9 N8 C32 109.10(19) . . ? C7 N8 Ag1 105.56(14) . . ? C7 N8 C32 109.77(18) . . ? C32 N8 Ag1 115.37(14) . . ? N8 C9 H9A 108.9 . . ? N8 C9 H9B 108.9 . . ? N8 C9 C10 113.6(2) . . ? H9A C9 H9B 107.7 . . ? C10 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C28 C27 C30 120.0(2) . . ? C28 C27 C26 120.7(2) . . ? C26 C27 C30 119.3(2) . . ? N5 C4 H4A 108.9 . . ? N5 C4 H4B 108.9 . . ? N5 C4 C3 113.52(18) . . ? H4A C4 H4B 107.7 . . ? C3 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C19 C20 H20 119.7 . . ? C19 C20 C15 120.5(2) . . ? C15 C20 H20 119.7 . . ? C38 C33 C32 121.5(2) . . ? C38 C33 C34 118.6(2) . . ? C34 C33 C32 119.9(2) . . ? N2 C14 H14A 108.8 . . ? N2 C14 H14B 108.8 . . ? N2 C14 C15 113.67(17) . . ? H14A C14 H14B 107.7 . . ? C15 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C17 C16 C15 121.1(2) . . ? C6 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? N8 C7 C6 112.3(2) . . ? N8 C7 H7A 109.1 . . ? N8 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? N2 C3 C4 113.98(19) . . ? N2 C3 H3A 108.8 . . ? N2 C3 H3B 108.8 . . ? C4 C3 H3A 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C20 C19 H19 120.3 . . ? C20 C19 C18 119.3(2) . . ? C18 C19 H19 120.3 . . ? N31 C30 C27 179.5(3) . . ? C33 C38 H38 119.8 . . ? C37 C38 C33 120.4(2) . . ? C37 C38 H38 119.8 . . ? N8 C32 C33 112.42(18) . . ? N8 C32 H32A 109.1 . . ? N8 C32 H32B 109.1 . . ? C33 C32 H32A 109.1 . . ? C33 C32 H32B 109.1 . . ? H32A C32 H32B 107.9 . . ? C20 C15 C14 121.4(2) . . ? C16 C15 C20 119.3(2) . . ? C16 C15 C14 119.2(2) . . ? N5 C23 C24 113.76(18) . . ? N5 C23 H23A 108.8 . . ? N5 C23 H23B 108.8 . . ? C24 C23 H23A 108.8 . . ? C24 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? N2 C13 C12 114.07(18) . . ? N2 C13 H13A 108.7 . . ? N2 C13 H13B 108.7 . . ? C12 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? C34 C35 C36 119.5(2) . . ? N11 C10 C9 112.41(19) . . ? N11 C10 H10A 109.1 . . ? N11 C10 H10B 109.1 . . ? C9 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C24 C29 H29 119.6 . . ? C28 C29 C24 120.8(2) . . ? C28 C29 H29 119.6 . . ? C35 C36 C37 119.8(2) . . ? C35 C36 C39 122.0(3) . . ? C37 C36 C39 118.2(3) . . ? C27 C28 H28 120.3 . . ? C29 C28 C27 119.4(2) . . ? C29 C28 H28 120.3 . . ? C19 C18 C21 120.9(2) . . ? C17 C18 C19 120.6(2) . . ? C17 C18 C21 118.5(2) . . ? C24 C25 H25 119.2 . . ? C26 C25 C24 121.5(2) . . ? C26 C25 H25 119.2 . . ? C27 C26 H26 120.6 . . ? C25 C26 C27 118.8(2) . . ? C25 C26 H26 120.6 . . ? N22 C21 C18 178.8(3) . . ? C33 C34 H34 119.3 . . ? C35 C34 C33 121.4(2) . . ? C35 C34 H34 119.3 . . ? C16 C17 C18 119.1(2) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C38 C37 C36 120.2(2) . . ? C38 C37 H37 119.9 . . ? C36 C37 H37 119.9 . . ? O51 Cl50 O53 110.86(13) . . ? O51 Cl50 O54 113.09(18) . . ? O51 Cl50 O52 105.4(2) . . ? O53 Cl50 O52 106.96(17) . . ? O54 Cl50 O53 113.59(15) . . ? O54 Cl50 O52 106.29(19) . . ? N40 C39 C36 175.9(4) . . ? C47 C42 C41 118.9(2) . . ? C43 C42 C41 122.3(2) . . ? C43 C42 C47 118.7(2) . . ? N11 C41 C42 113.51(19) . . ? N11 C41 H41A 108.9 . . ? N11 C41 H41B 108.9 . . ? C42 C41 H41A 108.9 . . ? C42 C41 H41B 108.9 . . ? H41A C41 H41B 107.7 . . ? C42 C47 H47 119.4 . . ? C46 C47 C42 121.2(2) . . ? C46 C47 H47 119.4 . . ? C47 C46 H46 120.5 . . ? C47 C46 C45 119.0(2) . . ? C45 C46 H46 120.5 . . ? C42 C43 H43 119.5 . . ? C44 C43 C42 121.0(2) . . ? C44 C43 H43 119.5 . . ? C43 C44 H44 120.4 . . ? C43 C44 C45 119.2(2) . . ? C45 C44 H44 120.4 . . ? N49 C48 C45 178.2(3) . . ? C46 C45 C48 119.3(2) . . ? C44 C45 C46 120.8(2) . . ? C44 C45 C48 120.0(2) . . ? C48 N49 Ag1 171.1(2) . 3_665 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Ag1 N2 C14 C15 -167.61(15) . . . . ? Ag1 N2 C3 C4 38.1(2) . . . . ? Ag1 N2 C13 C12 51.83(19) . . . . ? Ag1 N5 C6 C7 36.2(2) . . . . ? Ag1 N5 C4 C3 43.3(2) . . . . ? Ag1 N5 C23 C24 175.85(15) . . . . ? Ag1 N11 C10 C9 43.8(2) . . . . ? Ag1 N11 C41 C42 36.1(2) . . . . ? Ag1 N8 C9 C10 41.6(2) . . . . ? Ag1 N8 C7 C6 50.3(2) . . . . ? Ag1 N8 C32 C33 32.8(3) . . . . ? N2 Ag1 N5 C6 -135.42(15) . . . . ? N2 Ag1 N5 C4 -16.53(14) . . . . ? N2 Ag1 N5 C23 104.70(14) . . . . ? N2 Ag1 N11 C12 -7.07(13) . . . . ? N2 Ag1 N11 C10 109.44(14) . . . . ? N2 Ag1 N11 C41 -128.81(16) . . . . ? N2 Ag1 N8 C9 -78.92(15) . . . . ? N2 Ag1 N8 C7 38.81(17) . . . . ? N2 Ag1 N8 C32 160.18(15) . . . . ? N2 C14 C15 C20 -83.8(3) . . . . ? N2 C14 C15 C16 92.4(3) . . . . ? N5 Ag1 N2 C14 -134.78(16) . . . . ? N5 Ag1 N2 C3 -11.00(14) . . . . ? N5 Ag1 N2 C13 104.98(13) . . . . ? N5 Ag1 N11 C12 -69.11(14) . . . . ? N5 Ag1 N11 C10 47.39(16) . . . . ? N5 Ag1 N11 C41 169.15(14) . . . . ? N5 Ag1 N8 C9 -139.49(15) . . . . ? N5 Ag1 N8 C7 -21.77(14) . . . . ? N5 Ag1 N8 C32 99.61(17) . . . . ? N5 C6 C7 N8 -62.4(3) . . . . ? N5 C4 C3 N2 -58.7(3) . . . . ? C24 C29 C28 C27 0.3(3) . . . . ? C24 C25 C26 C27 1.4(4) . . . . ? C12 N11 C10 C9 156.5(2) . . . . ? C12 N11 C41 C42 -83.4(2) . . . . ? N11 Ag1 N2 C14 98.05(15) . . . . ? N11 Ag1 N2 C3 -138.18(15) . . . . ? N11 Ag1 N2 C13 -22.19(12) . . . . ? N11 Ag1 N5 C6 -71.64(15) . . . . ? N11 Ag1 N5 C4 47.25(16) . . . . ? N11 Ag1 N5 C23 168.48(12) . . . . ? N11 Ag1 N8 C9 -12.79(14) . . . . ? N11 Ag1 N8 C7 104.93(15) . . . . ? N11 Ag1 N8 C32 -133.69(17) . . . . ? N11 C12 C13 N2 -67.7(3) . . . . ? C6 N5 C4 C3 159.5(2) . . . . ? C6 N5 C23 C24 59.8(2) . . . . ? N8 Ag1 N2 C14 163.94(14) . . . . ? N8 Ag1 N2 C3 -72.29(16) . . . . ? N8 Ag1 N2 C13 43.70(14) . . . . ? N8 Ag1 N5 C6 -7.34(13) . . . . ? N8 Ag1 N5 C4 111.55(15) . . . . ? N8 Ag1 N5 C23 -127.22(14) . . . . ? N8 Ag1 N11 C12 -132.61(14) . . . . ? N8 Ag1 N11 C10 -16.11(14) . . . . ? N8 Ag1 N11 C41 105.65(16) . . . . ? N8 C9 C10 N11 -62.5(3) . . . . ? C9 N8 C7 C6 164.77(19) . . . . ? C9 N8 C32 C33 -86.4(2) . . . . ? C4 N5 C6 C7 -80.5(2) . . . . ? C4 N5 C23 C24 -66.7(2) . . . . ? C20 C19 C18 C21 -179.9(2) . . . . ? C20 C19 C18 C17 0.4(4) . . . . ? C33 C38 C37 C36 -1.7(4) . . . . ? C14 N2 C3 C4 162.94(18) . . . . ? C14 N2 C13 C12 -68.5(2) . . . . ? C7 N8 C9 C10 -72.6(2) . . . . ? C7 N8 C32 C33 151.9(2) . . . . ? C3 N2 C14 C15 70.6(2) . . . . ? C3 N2 C13 C12 165.23(18) . . . . ? C19 C20 C15 C14 174.7(2) . . . . ? C19 C20 C15 C16 -1.5(4) . . . . ? C19 C18 C21 N22 -167(100) . . . . ? C19 C18 C17 C16 0.3(4) . . . . ? C30 C27 C28 C29 177.7(2) . . . . ? C30 C27 C26 C25 -178.5(2) . . . . ? C38 C33 C32 N8 96.8(3) . . . . ? C38 C33 C34 C35 -0.8(3) . . . . ? C32 N8 C9 C10 166.42(19) . . . . ? C32 N8 C7 C6 -74.6(2) . . . . ? C32 C33 C38 C37 -179.6(2) . . . . ? C32 C33 C34 C35 -179.1(2) . . . . ? C15 C20 C19 C18 0.2(4) . . . . ? C15 C16 C17 C18 -1.7(4) . . . . ? C23 N5 C6 C7 151.66(19) . . . . ? C23 N5 C4 C3 -73.1(2) . . . . ? C23 C24 C29 C28 -173.5(2) . . . . ? C23 C24 C25 C26 172.7(2) . . . . ? C13 N2 C14 C15 -55.5(3) . . . . ? C13 N2 C3 C4 -69.9(2) . . . . ? C13 C12 N11 Ag1 37.1(2) . . . . ? C13 C12 N11 C10 -75.3(2) . . . . ? C13 C12 N11 C41 163.94(19) . . . . ? C35 C36 C37 C38 -0.2(4) . . . . ? C35 C36 C39 N40 129(6) . . . . ? C10 N11 C41 C42 155.30(19) . . . . ? C29 C24 C23 N5 88.8(3) . . . . ? C29 C24 C25 C26 -4.4(4) . . . . ? C36 C35 C34 C33 -1.1(4) . . . . ? C28 C27 C30 N31 -77(48) . . . . ? C28 C27 C26 C25 2.6(4) . . . . ? C25 C24 C23 N5 -88.2(3) . . . . ? C25 C24 C29 C28 3.5(4) . . . . ? C26 C27 C30 N31 104(48) . . . . ? C26 C27 C28 C29 -3.4(4) . . . . ? C21 C18 C17 C16 -179.4(2) . . . . ? C34 C33 C38 C37 2.1(3) . . . . ? C34 C33 C32 N8 -84.9(3) . . . . ? C34 C35 C36 C37 1.5(4) . . . . ? C34 C35 C36 C39 -176.9(2) . . . . ? C17 C16 C15 C20 2.3(4) . . . . ? C17 C16 C15 C14 -174.0(2) . . . . ? C17 C18 C21 N22 13(19) . . . . ? C37 C36 C39 N40 -49(6) . . . . ? C39 C36 C37 C38 178.3(2) . . . . ? C42 C47 C46 C45 -0.1(4) . . . . ? C42 C43 C44 C45 0.6(4) . . . . ? C41 N11 C10 C9 -82.9(2) . . . . ? C41 C42 C47 C46 -177.4(2) . . . . ? C41 C42 C43 C44 177.1(2) . . . . ? C47 C42 C41 N11 -90.0(3) . . . . ? C47 C42 C43 C44 -1.1(4) . . . . ? C47 C46 C45 C44 -0.3(4) . . . . ? C47 C46 C45 C48 -179.7(2) . . . . ? C43 C42 C41 N11 91.8(3) . . . . ? C43 C42 C47 C46 0.8(4) . . . . ? C43 C44 C45 C46 0.1(4) . . . . ? C43 C44 C45 C48 179.4(2) . . . . ? C45 C48 N49 Ag1 10(9) . . . 3_665 ? N49 Ag1 N2 C14 -29.04(16) 3_665 . . . ? N49 Ag1 N2 C3 94.73(15) 3_665 . . . ? N49 Ag1 N2 C13 -149.28(13) 3_665 . . . ? N49 Ag1 N5 C6 132.27(14) 3_665 . . . ? N49 Ag1 N5 C4 -108.84(15) 3_665 . . . ? N49 Ag1 N5 C23 12.39(15) 3_665 . . . ? N49 Ag1 N11 C12 81.59(15) 3_665 . . . ? N49 Ag1 N11 C10 -161.91(14) 3_665 . . . ? N49 Ag1 N11 C41 -40.15(18) 3_665 . . . ? N49 Ag1 N8 C9 121.93(16) 3_665 . . . ? N49 Ag1 N8 C7 -120.34(16) 3_665 . . . ? N49 Ag1 N8 C32 1.0(2) 3_665 . . . ? N49 C48 C45 C46 70(8) . . . . ? N49 C48 C45 C44 -110(8) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967730' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_date 2013-07-27 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C40 H44 Cl N4 Ni O8), Cl4 Ni' _chemical_formula_sum 'C80 H88 Cl6 N8 Ni3 O16' _chemical_formula_weight 1806.41 _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3410 1.1070 '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' _space_group_crystal_system tetragonal _space_group_IT_number 88 _space_group_name_H-M_alt 'I 41/a' _space_group_name_Hall '-I 4ad' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y+3/4, x+1/4, z+1/4' 3 '-x, -y+1/2, z' 4 'y+1/4, -x+1/4, z+1/4' 5 'x+1/2, y+1/2, z+1/2' 6 '-y+5/4, x+3/4, z+3/4' 7 '-x+1/2, -y+1, z+1/2' 8 'y+3/4, -x+3/4, z+3/4' 9 '-x, -y, -z' 10 'y-3/4, -x-1/4, -z-1/4' 11 'x, y-1/2, -z' 12 '-y-1/4, x-1/4, -z-1/4' 13 '-x+1/2, -y+1/2, -z+1/2' 14 'y-1/4, -x+1/4, -z+1/4' 15 'x+1/2, y, -z+1/2' 16 '-y+1/4, x+1/4, -z+1/4' _cell_length_a 16.298(2) _cell_length_b 16.298(2) _cell_length_c 30.945(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8220(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.946 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_process_details 'Multi-scan absorption correction within XDS suite' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 3752 _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_unetI/netI 0.0197 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 69812 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 1.41 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'Phi Scan' _diffrn_radiation_monochromator 'Silicon Double Crystal' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.71080 _diffrn_source 'Australian Synchrotron' _diffrn_standards_number 0 _reflns_number_gt 4394 _reflns_number_total 4959 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_collection 'BluIce (McPhillips, 2002)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_diff_density_max 2.201 _refine_diff_density_min -1.620 _refine_diff_density_rms 0.121 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4959 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0651 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1002P)^2^+27.8654P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1798 _refine_ls_wR_factor_ref 0.1867 _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. Structure model contains residual electron density peak of 2.201 co-axial with both nickel sites and one chloride position, occupying a special position along a fourfold axis, and is most likely an absorption artifact which was not able to be corrected using the software available in the XDS suite of programs. The DISP command was used to account for the non- standard wavelength of the synchrotron radiation used(0.71080 Angstroms), using Brennan and Cowan data for Ni f' and f'' 0.341 and 1.107, respectively. # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.250 0.125 176 53 ' ' 2 0.000 0.750 0.875 176 53 ' ' 3 0.500 0.250 0.375 176 53 ' ' 4 0.500 0.750 0.625 176 53 ' ' _platon_squeeze_details SQUEEZE was used to account for diffuse electron density located about a symmetry axis which was not able to be sensibly modelled, and suggests the presence of two ethanol molecules per Ni3 formula unit, as implied by other experimental techniques described in the text. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, {H21A,H21B} of C21, {H10A,H10B} of C10, {H11A,H11B} of C11, {H6A,H6B} of C6, {H9A,H9B} of C9, {H7A,H7B} of C7 At 1.5 times of: {H20,H30} of C13 2. Restrained distances H20-O20 0.84 with sigma of 0.02 H30-O30 0.84 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B), C6(H6A,H6B), C7(H7A,H7B) 3.b Aromatic/amide H refined with riding coordinates: C16(H16), C23(H23), C17(H17), C14(H14), C24(H24), C26(H26), C27(H27), C13(H13) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.2500 0.078831(17) 0.02423(17) Uani 1 2 d S . . Cl3 Cl 0.5000 0.2500 0.15085(3) 0.0280(2) Uani 1 2 d S . . N8 N 0.60220(16) 0.31959(16) 0.06089(8) 0.0245(5) Uani 1 1 d . . . O19 O 0.10323(16) 0.64440(17) 0.02128(8) 0.0355(5) Uani 1 1 d . . . C21 C 0.6387(2) 0.3693(2) 0.09689(10) 0.0279(6) Uani 1 1 d . . . H21A H 0.6562 0.3315 0.1202 0.033 Uiso 1 1 calc R . . H21B H 0.5956 0.4055 0.1089 0.033 Uiso 1 1 calc R . . C12 C 0.3245(2) 0.4612(2) 0.08142(10) 0.0280(6) Uani 1 1 d . . . N5 N 0.43011(16) 0.35338(16) 0.06058(8) 0.0256(5) Uani 1 1 d . . . C11 C 0.3796(2) 0.3916(2) 0.09578(10) 0.0289(6) Uani 1 1 d . . . H11A H 0.4171 0.4124 0.1184 0.035 Uiso 1 1 calc R . . H11B H 0.3451 0.3484 0.1090 0.035 Uiso 1 1 calc R . . O29 O 0.89515(18) 0.64107(18) 0.02165(10) 0.0447(7) Uani 1 1 d . . . C22 C 0.7112(2) 0.4215(2) 0.08404(10) 0.0295(7) Uani 1 1 d . . . C9 C 0.66360(19) 0.2614(2) 0.04253(10) 0.0273(6) Uani 1 1 d . . . H9A H 0.7040 0.2463 0.0651 0.033 Uiso 1 1 calc R . . H9B H 0.6935 0.2882 0.0185 0.033 Uiso 1 1 calc R . . O20 O 0.19971(16) 0.73141(16) 0.04416(11) 0.0433(7) Uani 1 1 d D . . C10 C 0.6207(2) 0.1848(2) 0.02608(10) 0.0274(6) Uani 1 1 d . . . H10A H 0.5853 0.1993 0.0012 0.033 Uiso 1 1 calc R . . H10B H 0.6622 0.1448 0.0160 0.033 Uiso 1 1 calc R . . O30 O 0.98121(17) 0.54783(18) 0.04822(11) 0.0476(7) Uani 1 1 d D . . C16 C 0.3020(2) 0.6068(2) 0.07102(11) 0.0302(7) Uani 1 1 d . . . H16 H 0.3210 0.6618 0.0733 0.036 Uiso 1 1 calc R . . C23 C 0.6976(2) 0.5019(2) 0.06931(12) 0.0360(7) Uani 1 1 d . . . H23 H 0.6431 0.5223 0.0682 0.043 Uiso 1 1 calc R . . C6 C 0.4884(2) 0.41377(19) 0.04155(11) 0.0283(6) Uani 1 1 d . . . H6A H 0.5027 0.4555 0.0635 0.034 Uiso 1 1 calc R . . H6B H 0.4618 0.4421 0.0170 0.034 Uiso 1 1 calc R . . C17 C 0.3518(2) 0.5423(2) 0.08453(11) 0.0299(6) Uani 1 1 d . . . H17 H 0.4047 0.5535 0.0960 0.036 Uiso 1 1 calc R . . C14 C 0.1962(2) 0.5095(2) 0.05153(11) 0.0306(7) Uani 1 1 d . . . H14 H 0.1432 0.4981 0.0402 0.037 Uiso 1 1 calc R . . C15 C 0.22428(19) 0.5907(2) 0.05406(10) 0.0277(6) Uani 1 1 d . . . C25 C 0.8401(2) 0.5223(2) 0.05726(12) 0.0364(7) Uani 1 1 d . . . C7 C 0.56591(19) 0.37151(19) 0.02602(9) 0.0258(6) Uani 1 1 d . . . H7A H 0.5529 0.3368 0.0007 0.031 Uiso 1 1 calc R . . H7B H 0.6064 0.4133 0.0169 0.031 Uiso 1 1 calc R . . C24 C 0.7612(2) 0.5521(2) 0.05643(12) 0.0365(7) Uani 1 1 d . . . H24 H 0.7506 0.6066 0.0471 0.044 Uiso 1 1 calc R . . C18 C 0.1698(2) 0.6575(2) 0.03844(11) 0.0321(7) Uani 1 1 d . . . C28 C 0.9085(2) 0.5763(2) 0.04102(12) 0.0378(8) Uani 1 1 d . . . C26 C 0.8567(2) 0.4444(3) 0.07237(12) 0.0387(8) Uani 1 1 d . . . H26 H 0.9116 0.4250 0.0737 0.046 Uiso 1 1 calc R . . C27 C 0.7916(2) 0.3940(2) 0.08586(13) 0.0386(8) Uani 1 1 d . . . H27 H 0.8028 0.3404 0.0964 0.046 Uiso 1 1 calc R . . Ni2 Ni 0.5000 0.7500 0.1250 0.0294(2) Uani 1 4 d S . . Cl4 Cl 0.40089(6) 0.70720(5) 0.17087(3) 0.0374(2) Uani 1 1 d . . . C13 C 0.2455(2) 0.4464(2) 0.06544(11) 0.0306(7) Uani 1 1 d . . . H13 H 0.2257 0.3916 0.0642 0.037 Uiso 1 1 calc R . . H20 H 0.163(2) 0.762(2) 0.0344(15) 0.046 Uiso 1 1 d D . . H30 H 1.016(2) 0.577(2) 0.0348(14) 0.046 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 Ni1 0.0287(3) 0.0255(3) 0.0186(3) 0.000 0.000 -0.0026(2) Cl3 0.0345(5) 0.0313(5) 0.0182(4) 0.000 0.000 -0.0033(4) N8 0.0288(12) 0.0260(12) 0.0188(11) -0.0001(9) -0.0004(9) -0.0026(10) O19 0.0325(12) 0.0431(14) 0.0310(12) 0.0002(10) -0.0004(10) 0.0021(10) C21 0.0336(16) 0.0309(15) 0.0191(13) -0.0038(11) -0.0004(11) -0.0064(13) C12 0.0320(15) 0.0310(15) 0.0211(14) -0.0005(11) 0.0046(12) -0.0009(12) N5 0.0287(12) 0.0273(12) 0.0206(12) 0.0027(9) 0.0023(10) -0.0037(10) C11 0.0357(16) 0.0290(15) 0.0220(14) 0.0012(11) 0.0027(12) -0.0011(13) O29 0.0413(15) 0.0386(14) 0.0542(17) 0.0015(12) 0.0008(12) -0.0016(11) C22 0.0290(15) 0.0352(16) 0.0243(15) -0.0081(12) 0.0016(12) -0.0068(12) C9 0.0275(14) 0.0315(15) 0.0228(14) -0.0013(12) 0.0015(11) -0.0014(12) O20 0.0304(13) 0.0340(13) 0.0656(19) 0.0071(12) 0.0026(12) 0.0026(10) C10 0.0308(15) 0.0315(15) 0.0199(14) -0.0014(11) 0.0022(11) -0.0006(12) O30 0.0330(14) 0.0437(16) 0.066(2) -0.0050(14) 0.0090(13) -0.0034(11) C16 0.0318(16) 0.0300(15) 0.0289(15) -0.0025(12) 0.0050(12) -0.0029(12) C23 0.0394(18) 0.0363(18) 0.0322(17) -0.0042(14) -0.0005(14) -0.0073(14) C6 0.0317(15) 0.0252(14) 0.0281(15) 0.0051(12) 0.0037(12) -0.0040(12) C17 0.0312(16) 0.0304(15) 0.0281(15) -0.0004(12) 0.0013(12) -0.0014(12) C14 0.0287(15) 0.0354(16) 0.0277(15) -0.0052(13) 0.0053(12) -0.0015(13) C15 0.0287(15) 0.0327(16) 0.0218(13) -0.0010(12) 0.0061(11) 0.0029(12) C25 0.0443(19) 0.0359(18) 0.0291(16) -0.0064(14) 0.0001(14) -0.0012(15) C7 0.0291(15) 0.0277(14) 0.0207(14) 0.0038(11) 0.0015(11) -0.0035(12) C24 0.0413(19) 0.0359(17) 0.0322(17) -0.0023(14) -0.0006(14) -0.0044(15) C18 0.0328(16) 0.0352(17) 0.0283(15) 0.0021(13) 0.0102(13) 0.0024(13) C28 0.047(2) 0.0338(17) 0.0331(17) -0.0044(14) -0.0017(15) -0.0026(15) C26 0.0331(17) 0.048(2) 0.0353(18) -0.0080(15) -0.0020(14) 0.0053(15) C27 0.0377(18) 0.0355(18) 0.043(2) -0.0065(15) -0.0101(15) 0.0025(14) Ni2 0.0357(3) 0.0357(3) 0.0169(4) 0.000 0.000 0.000 Cl4 0.0479(5) 0.0389(4) 0.0253(4) 0.0031(3) 0.0078(3) -0.0031(4) C13 0.0319(16) 0.0289(15) 0.0310(16) -0.0043(12) 0.0060(13) -0.0034(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 Cl3 2.2286(12) . ? Ni1 N8 2.090(3) 3_655 ? Ni1 N8 2.090(3) . ? Ni1 N5 2.111(3) 3_655 ? Ni1 N5 2.111(3) . ? N8 C21 1.501(4) . ? N8 C9 1.491(4) . ? N8 C7 1.493(4) . ? O19 C18 1.227(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.508(4) . ? C12 C11 1.514(5) . ? C12 C17 1.397(5) . ? C12 C13 1.400(5) . ? N5 C11 1.500(4) . ? N5 C10 1.488(4) 3_655 ? N5 C6 1.489(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? O29 C28 1.232(5) . ? C22 C23 1.405(5) . ? C22 C27 1.386(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.519(4) . ? O20 C18 1.312(4) . ? O20 H20 0.841(19) . ? C10 N5 1.488(4) 3_655 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? O30 C28 1.293(5) . ? O30 H30 0.848(19) . ? C16 H16 0.9500 . ? C16 C17 1.392(5) . ? C16 C15 1.396(5) . ? C23 H23 0.9500 . ? C23 C24 1.379(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.517(4) . ? C17 H17 0.9500 . ? C14 H14 0.9500 . ? C14 C15 1.403(5) . ? C14 C13 1.375(5) . ? C15 C18 1.485(5) . ? C25 C24 1.376(5) . ? C25 C28 1.506(5) . ? C25 C26 1.379(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C24 H24 0.9500 . ? C26 H26 0.9500 . ? C26 C27 1.406(6) . ? C27 H27 0.9500 . ? Ni2 Cl4 2.2608(9) 3_665 ? Ni2 Cl4 2.2607(9) . ? Ni2 Cl4 2.2608(9) 14_565 ? Ni2 Cl4 2.2608(9) 16_655 ? C13 H13 0.9500 . ? 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 N8 Ni1 Cl3 105.40(7) 3_655 . ? N8 Ni1 Cl3 105.41(7) . . ? N8 Ni1 N8 149.19(14) 3_655 . ? N8 Ni1 N5 86.10(10) 3_655 . ? N8 Ni1 N5 86.10(10) . 3_655 ? N8 Ni1 N5 85.75(10) . . ? N8 Ni1 N5 85.75(10) 3_655 3_655 ? N5 Ni1 Cl3 105.52(7) 3_655 . ? N5 Ni1 Cl3 105.52(7) . . ? N5 Ni1 N5 148.96(14) 3_655 . ? C21 N8 Ni1 114.33(19) . . ? C9 N8 Ni1 106.93(18) . . ? C9 N8 C21 111.1(2) . . ? C9 N8 C7 110.5(2) . . ? C7 N8 Ni1 100.59(18) . . ? C7 N8 C21 112.8(2) . . ? N8 C21 H21A 108.6 . . ? N8 C21 H21B 108.6 . . ? N8 C21 C22 114.8(2) . . ? H21A C21 H21B 107.5 . . ? C22 C21 H21A 108.6 . . ? C22 C21 H21B 108.6 . . ? C17 C12 C11 120.0(3) . . ? C17 C12 C13 118.7(3) . . ? C13 C12 C11 121.3(3) . . ? C11 N5 Ni1 115.65(19) . . ? C10 N5 Ni1 99.13(19) 3_655 . ? C10 N5 C11 112.9(3) 3_655 . ? C10 N5 C6 110.4(2) 3_655 . ? C6 N5 Ni1 106.81(19) . . ? C6 N5 C11 111.3(2) . . ? C12 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? N5 C11 C12 115.0(3) . . ? N5 C11 H11A 108.5 . . ? N5 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C23 C22 C21 119.3(3) . . ? C27 C22 C21 123.2(3) . . ? C27 C22 C23 117.6(3) . . ? N8 C9 H9A 109.7 . . ? N8 C9 H9B 109.7 . . ? N8 C9 C10 110.0(3) . . ? H9A C9 H9B 108.2 . . ? C10 C9 H9A 109.7 . . ? C10 C9 H9B 109.7 . . ? C18 O20 H20 104(3) . . ? N5 C10 C9 111.1(2) 3_655 . ? N5 C10 H10A 109.4 3_655 . ? N5 C10 H10B 109.4 3_655 . ? C9 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C28 O30 H30 109(3) . . ? C17 C16 H16 120.0 . . ? C17 C16 C15 120.0(3) . . ? C15 C16 H16 120.0 . . ? C22 C23 H23 119.0 . . ? C24 C23 C22 122.0(4) . . ? C24 C23 H23 119.0 . . ? N5 C6 H6A 109.5 . . ? N5 C6 H6B 109.5 . . ? N5 C6 C7 110.9(3) . . ? H6A C6 H6B 108.1 . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C12 C17 H17 119.7 . . ? C16 C17 C12 120.6(3) . . ? C16 C17 H17 119.7 . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C13 C14 C15 119.8(3) . . ? C16 C15 C14 119.6(3) . . ? C16 C15 C18 121.8(3) . . ? C14 C15 C18 118.5(3) . . ? C24 C25 C28 118.6(3) . . ? C24 C25 C26 121.0(4) . . ? C26 C25 C28 120.5(4) . . ? N8 C7 C6 111.0(2) . . ? N8 C7 H7A 109.4 . . ? N8 C7 H7B 109.4 . . ? C6 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C23 C24 H24 120.4 . . ? C25 C24 C23 119.2(4) . . ? C25 C24 H24 120.4 . . ? O19 C18 O20 123.1(3) . . ? O19 C18 C15 122.9(3) . . ? O20 C18 C15 114.0(3) . . ? O29 C28 O30 123.6(4) . . ? O29 C28 C25 122.2(4) . . ? O30 C28 C25 114.2(3) . . ? C25 C26 H26 120.3 . . ? C25 C26 C27 119.4(4) . . ? C27 C26 H26 120.3 . . ? C22 C27 C26 120.9(4) . . ? C22 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? Cl4 Ni2 Cl4 102.21(5) . 3_665 ? Cl4 Ni2 Cl4 113.22(3) . 16_655 ? Cl4 Ni2 Cl4 113.22(3) 3_665 16_655 ? Cl4 Ni2 Cl4 113.22(3) . 14_565 ? Cl4 Ni2 Cl4 113.22(3) 3_665 14_565 ? Cl4 Ni2 Cl4 102.21(5) 16_655 14_565 ? C12 C13 H13 119.4 . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13 119.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O20 H20 O29 0.841(19) 1.88(2) 2.682(4) 160(5) 3_665 O30 H30 O19 0.848(19) 1.85(2) 2.670(4) 164(5) 1_655 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Ni1 N8 C21 C22 -178.5(2) . . . . ? Ni1 N8 C9 C10 23.7(3) . . . . ? Ni1 N8 C7 C6 51.8(3) . . . . ? Ni1 N5 C11 C12 -175.2(2) . . . . ? Ni1 N5 C6 C7 21.9(3) . . . . ? Cl3 Ni1 N8 C21 -14.2(2) . . . . ? Cl3 Ni1 N8 C9 109.22(17) . . . . ? Cl3 Ni1 N8 C7 -135.31(16) . . . . ? Cl3 Ni1 N5 C11 -14.3(2) . . . . ? Cl3 Ni1 N5 C10 -135.21(16) . . . 3_655 ? Cl3 Ni1 N5 C6 110.17(18) . . . . ? N8 Ni1 N8 C21 165.8(2) 3_655 . . . ? N8 Ni1 N8 C9 -70.78(17) 3_655 . . . ? N8 Ni1 N8 C7 44.69(16) 3_655 . . . ? N8 Ni1 N5 C11 -119.1(2) . . . . ? N8 Ni1 N5 C11 90.7(2) 3_655 . . . ? N8 Ni1 N5 C10 -30.30(18) 3_655 . . 3_655 ? N8 Ni1 N5 C10 119.96(18) . . . 3_655 ? N8 Ni1 N5 C6 5.3(2) . . . . ? N8 Ni1 N5 C6 -144.9(2) 3_655 . . . ? N8 C21 C22 C23 89.7(4) . . . . ? N8 C21 C22 C27 -90.1(4) . . . . ? N8 C9 C10 N5 -54.9(3) . . . 3_655 ? C21 N8 C9 C10 149.1(2) . . . . ? C21 N8 C7 C6 -70.4(3) . . . . ? C21 C22 C23 C24 -178.9(3) . . . . ? C21 C22 C27 C26 178.2(3) . . . . ? N5 Ni1 N8 C21 -119.2(2) 3_655 . . . ? N5 Ni1 N8 C21 90.8(2) . . . . ? N5 Ni1 N8 C9 -145.84(19) . . . . ? N5 Ni1 N8 C9 4.19(19) 3_655 . . . ? N5 Ni1 N8 C7 -30.37(18) . . . . ? N5 Ni1 N8 C7 119.66(18) 3_655 . . . ? N5 Ni1 N5 C11 165.7(2) 3_655 . . . ? N5 Ni1 N5 C10 44.79(16) 3_655 . . 3_655 ? N5 Ni1 N5 C6 -69.83(18) 3_655 . . . ? N5 C6 C7 N8 -52.2(3) . . . . ? C11 C12 C17 C16 179.3(3) . . . . ? C11 C12 C13 C14 -178.6(3) . . . . ? C11 N5 C6 C7 148.9(3) . . . . ? C22 C23 C24 C25 1.2(5) . . . . ? C9 N8 C21 C22 60.4(4) . . . . ? C9 N8 C7 C6 164.6(3) . . . . ? C10 N5 C11 C12 -62.0(3) 3_655 . . . ? C10 N5 C6 C7 -84.9(3) 3_655 . . . ? C16 C15 C18 O19 175.9(3) . . . . ? C16 C15 C18 O20 -3.3(4) . . . . ? C23 C22 C27 C26 -1.6(5) . . . . ? C6 N5 C11 C12 62.8(4) . . . . ? C17 C12 C11 N5 -94.1(4) . . . . ? C17 C12 C13 C14 2.3(5) . . . . ? C17 C16 C15 C14 1.2(5) . . . . ? C17 C16 C15 C18 -178.8(3) . . . . ? C14 C15 C18 O19 -4.1(5) . . . . ? C14 C15 C18 O20 176.7(3) . . . . ? C15 C16 C17 C12 -0.2(5) . . . . ? C15 C14 C13 C12 -1.3(5) . . . . ? C25 C26 C27 C22 0.2(6) . . . . ? C7 N8 C21 C22 -64.3(4) . . . . ? C7 N8 C9 C10 -84.9(3) . . . . ? C24 C25 C28 O29 -10.3(5) . . . . ? C24 C25 C28 O30 171.4(3) . . . . ? C24 C25 C26 C27 2.0(6) . . . . ? C28 C25 C24 C23 177.0(3) . . . . ? C28 C25 C26 C27 -177.7(3) . . . . ? C26 C25 C24 C23 -2.6(6) . . . . ? C26 C25 C28 O29 169.3(4) . . . . ? C26 C25 C28 O30 -9.0(5) . . . . ? C27 C22 C23 C24 0.9(5) . . . . ? C13 C12 C11 N5 86.7(4) . . . . ? C13 C12 C17 C16 -1.5(5) . . . . ? C13 C14 C15 C16 -0.5(5) . . . . ? C13 C14 C15 C18 179.5(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967731' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_date 2013-09-05 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'Cl4 Co, 2(C40 H44 Cl Co N4 O8)' _chemical_formula_sum 'C80 H88 Cl6 Co3 N8 O16' _chemical_formula_weight 1807.07 _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3500 0.9680 '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' _space_group_crystal_system tetragonal _space_group_IT_number 88 _space_group_name_H-M_alt 'I 41/a' _space_group_name_Hall '-I 4ad' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y+3/4, x+1/4, z+1/4' 3 '-x, -y+1/2, z' 4 'y+1/4, -x+1/4, z+1/4' 5 'x+1/2, y+1/2, z+1/2' 6 '-y+5/4, x+3/4, z+3/4' 7 '-x+1/2, -y+1, z+1/2' 8 'y+3/4, -x+3/4, z+3/4' 9 '-x, -y, -z' 10 'y-3/4, -x-1/4, -z-1/4' 11 'x, y-1/2, -z' 12 '-y-1/4, x-1/4, -z-1/4' 13 '-x+1/2, -y+1/2, -z+1/2' 14 'y-1/4, -x+1/4, -z+1/4' 15 'x+1/2, y, -z+1/2' 16 '-y+1/4, x+1/4, -z+1/4' _cell_length_a 16.353(2) _cell_length_b 16.353(2) _cell_length_c 30.894(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8262(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.859 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Multi-scan routine within XDS' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 3740 _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0661 _diffrn_reflns_av_unetI/netI 0.0230 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 70088 _diffrn_reflns_theta_full 27.99 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_min 1.41 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'Phi Scan' _diffrn_radiation_monochromator 'Silicon Double Crystal' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.71080 _diffrn_source 'Australian Synchrotron' _diffrn_standards_number 0 _reflns_number_gt 4355 _reflns_number_total 4977 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_collection 'BluIce (McPhillips, 2002)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_diff_density_max 1.538 _refine_diff_density_min -1.628 _refine_diff_density_rms 0.119 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4977 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0782 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+41.5897P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2101 _refine_ls_wR_factor_ref 0.2185 _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. Structure model contains residual electron density peaks coaxial with the marocyclic Ni-Cl vector parallel to a fourfold axis, which is ascribed to an absorption effect. The DISP command was used to account for non-standard wavelength of 0.71080 angstrom, using Brennan and Cowan values of 0.350 and 0.968 for Co f' and f'', respectively. # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.750 0.375 176 38 ' ' 2 0.000 0.250 0.625 176 38 ' ' 3 0.500 0.750 0.125 176 38 ' ' 4 0.500 0.250 0.875 176 38 ' ' _platon_squeeze_details SQUEEZE was used to account for electron density within pockets of disordered solvent, suggesting the presence of two ethanol molecules per Co3 formula unit. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2. Restrained distances O20-H20 0.84 with sigma of 0.02 H30-O30 0.84 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C11(H11A,H11B), C21(H21A,H21B), C9(H9A,H9B), C7(H7A,H7B), C6(H6A,H6B) 3.b Aromatic/amide H refined with riding coordinates: C23(H23), C24(H24), C17(H17), C27(H27), C13(H13), C14(H14), C26(H26), C16(H16) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Co2 Co 0.0000 0.2500 0.1250 0.0308(3) Uani 1 4 d S . . Cl4 Cl 0.04294(6) 0.35201(7) 0.08041(3) 0.0391(3) Uani 1 1 d . . . Co1 Co 0.0000 0.7500 0.08507(2) 0.0317(2) Uani 1 2 d S . . Cl3 Cl 0.0000 0.7500 0.15607(4) 0.0386(3) Uani 1 2 d S . . C22 C -0.1760(2) 0.5385(2) 0.08077(11) 0.0301(7) Uani 1 1 d . . . N5 N 0.10118(19) 0.68028(18) 0.06111(9) 0.0280(6) Uani 1 1 d . . . C12 C 0.2110(2) 0.5787(2) 0.08383(11) 0.0309(7) Uani 1 1 d . . . O29 O -0.39777(18) 0.35803(19) 0.02026(9) 0.0393(6) Uani 1 1 d . . . C10 C 0.1622(2) 0.7384(2) 0.04273(12) 0.0305(7) Uani 1 1 d . . . H10A H 0.1919 0.7118 0.0186 0.037 Uiso 1 1 calc R . . H10B H 0.2025 0.7533 0.0653 0.037 Uiso 1 1 calc R . . C11 C 0.1383(2) 0.6300(2) 0.09682(12) 0.0318(7) Uani 1 1 d . . . H11A H 0.0956 0.5933 0.1086 0.038 Uiso 1 1 calc R . . H11B H 0.1553 0.6673 0.1204 0.038 Uiso 1 1 calc R . . C21 C -0.1209(2) 0.6076(2) 0.09555(12) 0.0314(7) Uani 1 1 d . . . H21A H -0.1553 0.6504 0.1091 0.038 Uiso 1 1 calc R . . H21B H -0.0837 0.5864 0.1182 0.038 Uiso 1 1 calc R . . N8 N -0.07017(19) 0.64668(19) 0.06080(10) 0.0288(6) Uani 1 1 d . . . O20 O 0.4797(2) 0.4520(2) 0.04776(14) 0.0564(9) Uani 1 1 d D . . H20 H 0.522(3) 0.427(4) 0.040(2) 0.085 Uiso 1 1 d D . . O30 O -0.30180(19) 0.27004(19) 0.04255(13) 0.0496(8) Uani 1 1 d D . . H30 H -0.335(3) 0.234(3) 0.035(2) 0.074 Uiso 1 1 d D . . C9 C 0.1199(2) 0.8150(2) 0.02632(11) 0.0302(7) Uani 1 1 d . . . H9A H 0.1614 0.8545 0.0160 0.036 Uiso 1 1 calc R . . H9B H 0.0842 0.8008 0.0015 0.036 Uiso 1 1 calc R . . C23 C -0.1493(2) 0.4579(2) 0.08376(12) 0.0317(7) Uani 1 1 d . . . H23 H -0.0967 0.4463 0.0952 0.038 Uiso 1 1 calc R . . C7 C -0.0123(2) 0.5865(2) 0.04151(12) 0.0317(7) Uani 1 1 d . . . H7A H -0.0389 0.5585 0.0168 0.038 Uiso 1 1 calc R . . H7B H 0.0020 0.5446 0.0634 0.038 Uiso 1 1 calc R . . C24 C -0.1995(2) 0.3941(2) 0.06997(12) 0.0311(7) Uani 1 1 d . . . H24 H -0.1810 0.3392 0.0720 0.037 Uiso 1 1 calc R . . C15 C 0.3383(3) 0.4779(3) 0.05708(13) 0.0432(10) Uani 1 1 d . . . C25 C -0.2769(2) 0.4107(2) 0.05316(11) 0.0299(7) Uani 1 1 d . . . C17 C 0.1987(3) 0.4991(3) 0.06893(13) 0.0409(9) Uani 1 1 d . . . H17 H 0.1444 0.4786 0.0676 0.049 Uiso 1 1 calc R . . C6 C 0.0645(2) 0.6290(2) 0.02611(11) 0.0291(7) Uani 1 1 d . . . H6A H 0.1049 0.5875 0.0166 0.035 Uiso 1 1 calc R . . H6B H 0.0514 0.6640 0.0009 0.035 Uiso 1 1 calc R . . O19 O 0.3945(2) 0.3600(2) 0.02064(12) 0.0522(8) Uani 1 1 d . . . C27 C -0.2544(2) 0.5542(2) 0.06508(12) 0.0328(8) Uani 1 1 d . . . H27 H -0.2737 0.6089 0.0639 0.039 Uiso 1 1 calc R . . C13 C 0.2910(3) 0.6064(3) 0.08601(16) 0.0439(10) Uani 1 1 d . . . H13 H 0.3023 0.6599 0.0965 0.053 Uiso 1 1 calc R . . C14 C 0.3565(3) 0.5546(3) 0.07248(14) 0.0460(10) Uani 1 1 d . . . H14 H 0.4115 0.5729 0.0741 0.055 Uiso 1 1 calc R . . C26 C -0.3043(2) 0.4913(2) 0.05120(12) 0.0333(8) Uani 1 1 d . . . H26 H -0.3574 0.5031 0.0403 0.040 Uiso 1 1 calc R . . C16 C 0.2619(3) 0.4487(3) 0.05599(14) 0.0438(10) Uani 1 1 d . . . H16 H 0.2514 0.3945 0.0465 0.053 Uiso 1 1 calc R . . C28 C -0.3311(2) 0.3444(2) 0.03723(12) 0.0346(8) Uani 1 1 d . . . C18 C 0.4077(3) 0.4243(3) 0.04061(15) 0.0460(10) 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 Co2 0.0371(4) 0.0371(4) 0.0184(4) 0.000 0.000 0.000 Cl4 0.0408(5) 0.0503(6) 0.0262(4) 0.0100(4) 0.0022(4) -0.0023(4) Co1 0.0390(4) 0.0327(4) 0.0235(4) 0.000 0.000 0.0021(3) Cl3 0.0451(7) 0.0440(7) 0.0267(6) 0.000 0.000 0.0074(6) C22 0.0367(18) 0.0317(17) 0.0218(15) -0.0009(13) 0.0033(13) 0.0016(14) N5 0.0342(15) 0.0297(14) 0.0201(13) 0.0007(11) -0.0030(11) 0.0038(12) C12 0.0333(18) 0.0349(18) 0.0243(16) 0.0090(13) 0.0010(13) 0.0033(14) O29 0.0329(14) 0.0498(17) 0.0351(14) -0.0007(12) -0.0001(11) -0.0024(12) C10 0.0318(17) 0.0327(17) 0.0271(16) 0.0005(14) 0.0002(13) 0.0016(14) C11 0.0390(19) 0.0334(18) 0.0229(16) 0.0022(13) -0.0026(14) 0.0069(15) C21 0.0399(19) 0.0310(17) 0.0234(16) -0.0011(13) 0.0031(14) 0.0016(15) N8 0.0348(15) 0.0290(14) 0.0227(13) -0.0030(11) 0.0034(11) 0.0032(12) O20 0.0416(18) 0.051(2) 0.077(3) 0.0120(18) 0.0120(17) 0.0031(14) O30 0.0332(15) 0.0388(16) 0.077(2) -0.0113(16) -0.0001(15) -0.0018(12) C9 0.0361(18) 0.0339(18) 0.0206(15) 0.0025(13) 0.0009(13) 0.0000(14) C23 0.0343(18) 0.0334(18) 0.0274(17) -0.0010(14) 0.0006(14) 0.0023(14) C7 0.0365(18) 0.0303(17) 0.0283(17) -0.0048(14) 0.0040(14) 0.0037(14) C24 0.0335(18) 0.0320(18) 0.0279(17) 0.0012(14) 0.0034(14) 0.0039(14) C15 0.062(3) 0.040(2) 0.0270(18) 0.0070(16) 0.0007(18) 0.0008(19) C25 0.0312(17) 0.0361(18) 0.0224(15) 0.0007(13) 0.0061(13) -0.0026(14) C17 0.050(2) 0.041(2) 0.0314(19) 0.0024(16) -0.0029(17) 0.0102(18) C6 0.0363(18) 0.0320(17) 0.0190(15) -0.0038(12) 0.0012(13) 0.0017(14) O19 0.0501(19) 0.0474(18) 0.059(2) -0.0006(16) 0.0030(15) 0.0017(15) C27 0.0345(19) 0.0319(18) 0.0321(18) 0.0034(14) 0.0061(14) 0.0031(14) C13 0.041(2) 0.040(2) 0.050(3) 0.0111(18) -0.0123(19) -0.0050(17) C14 0.035(2) 0.066(3) 0.037(2) 0.012(2) -0.0052(17) -0.0093(19) C26 0.0306(17) 0.040(2) 0.0294(17) 0.0060(15) 0.0046(14) 0.0024(15) C16 0.054(3) 0.043(2) 0.034(2) 0.0026(17) -0.0020(18) 0.0077(19) C28 0.0349(19) 0.039(2) 0.0293(17) -0.0043(15) 0.0089(15) -0.0031(15) C18 0.061(3) 0.040(2) 0.037(2) 0.0050(18) -0.005(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co2 Cl4 2.2745(10) 14 ? Co2 Cl4 2.2745(10) 3 ? Co2 Cl4 2.2745(10) . ? Co2 Cl4 2.2745(10) 16 ? Co1 Cl3 2.1935(16) . ? Co1 N5 2.141(3) 3_565 ? Co1 N5 2.141(3) . ? Co1 N8 2.176(3) 3_565 ? Co1 N8 2.176(3) . ? C22 C21 1.517(5) . ? C22 C23 1.391(5) . ? C22 C27 1.394(5) . ? N5 C10 1.490(5) . ? N5 C11 1.504(4) . ? N5 C6 1.494(4) . ? C12 C11 1.509(5) . ? C12 C17 1.395(6) . ? C12 C13 1.387(6) . ? O29 C28 1.231(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C9 1.519(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 N8 1.499(5) . ? N8 C9 1.479(5) 3_565 ? N8 C7 1.489(4) . ? O20 H20 0.84(2) . ? O20 C18 1.281(6) . ? O30 H30 0.84(2) . ? O30 C28 1.317(5) . ? C9 N8 1.479(5) 3_565 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C23 H23 0.9500 . ? C23 C24 1.394(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C6 1.513(5) . ? C24 H24 0.9500 . ? C24 C25 1.394(5) . ? C15 C14 1.374(7) . ? C15 C16 1.338(7) . ? C15 C18 1.521(7) . ? C25 C26 1.395(5) . ? C25 C28 1.484(5) . ? C17 H17 0.9500 . ? C17 C16 1.381(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? O19 C18 1.239(6) . ? C27 H27 0.9500 . ? C27 C26 1.381(6) . ? C13 H13 0.9500 . ? C13 C14 1.428(7) . ? C14 H14 0.9500 . ? C26 H26 0.9500 . ? C16 H16 0.9500 . ? 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 Cl4 Co2 Cl4 111.51(3) 3 14 ? Cl4 Co2 Cl4 111.51(3) 3 16 ? Cl4 Co2 Cl4 105.46(5) 14 16 ? Cl4 Co2 Cl4 105.46(5) 3 . ? Cl4 Co2 Cl4 111.51(3) 14 . ? Cl4 Co2 Cl4 111.51(3) 16 . ? N5 Co1 Cl3 110.22(8) . . ? N5 Co1 Cl3 110.22(8) 3_565 . ? N5 Co1 N5 139.55(16) 3_565 . ? N5 Co1 N8 83.50(12) 3_565 . ? N5 Co1 N8 83.50(12) . 3_565 ? N5 Co1 N8 82.82(11) 3_565 3_565 ? N5 Co1 N8 82.82(11) . . ? N8 Co1 Cl3 110.16(8) 3_565 . ? N8 Co1 Cl3 110.15(8) . . ? N8 Co1 N8 139.69(16) 3_565 . ? C23 C22 C21 120.0(3) . . ? C23 C22 C27 119.1(4) . . ? C27 C22 C21 120.9(3) . . ? C10 N5 Co1 108.0(2) . . ? C10 N5 C11 111.0(3) . . ? C10 N5 C6 110.5(3) . . ? C11 N5 Co1 110.4(2) . . ? C6 N5 Co1 103.8(2) . . ? C6 N5 C11 112.7(3) . . ? C17 C12 C11 119.6(4) . . ? C13 C12 C11 123.3(4) . . ? C13 C12 C17 117.2(4) . . ? N5 C10 H10A 109.6 . . ? N5 C10 H10B 109.6 . . ? N5 C10 C9 110.4(3) . . ? H10A C10 H10B 108.1 . . ? C9 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? N5 C11 C12 115.3(3) . . ? N5 C11 H11A 108.5 . . ? N5 C11 H11B 108.5 . . ? C12 C11 H11A 108.5 . . ? C12 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? C22 C21 H21A 108.4 . . ? C22 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? N8 C21 C22 115.5(3) . . ? N8 C21 H21A 108.4 . . ? N8 C21 H21B 108.4 . . ? C21 N8 Co1 112.1(2) . . ? C9 N8 Co1 102.1(2) 3_565 . ? C9 N8 C21 113.1(3) 3_565 . ? C9 N8 C7 109.9(3) 3_565 . ? C7 N8 Co1 108.4(2) . . ? C7 N8 C21 110.9(3) . . ? C18 O20 H20 122(5) . . ? C28 O30 H30 112(5) . . ? C10 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? N8 C9 C10 111.0(3) 3_565 . ? N8 C9 H9A 109.4 3_565 . ? N8 C9 H9B 109.4 3_565 . ? H9A C9 H9B 108.0 . . ? C22 C23 H23 119.9 . . ? C22 C23 C24 120.2(4) . . ? C24 C23 H23 119.9 . . ? N8 C7 H7A 109.6 . . ? N8 C7 H7B 109.6 . . ? N8 C7 C6 110.5(3) . . ? H7A C7 H7B 108.1 . . ? C6 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? C23 C24 H24 119.9 . . ? C23 C24 C25 120.2(4) . . ? C25 C24 H24 119.9 . . ? C14 C15 C18 118.7(4) . . ? C16 C15 C14 122.4(5) . . ? C16 C15 C18 118.9(4) . . ? C24 C25 C26 119.5(4) . . ? C24 C25 C28 121.6(4) . . ? C26 C25 C28 119.0(3) . . ? C12 C17 H17 118.5 . . ? C16 C17 C12 123.0(4) . . ? C16 C17 H17 118.5 . . ? N5 C6 C7 111.3(3) . . ? N5 C6 H6A 109.4 . . ? N5 C6 H6B 109.4 . . ? C7 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C22 C27 H27 119.5 . . ? C26 C27 C22 120.9(4) . . ? C26 C27 H27 119.5 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 119.9(4) . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 118.8(4) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C25 C26 H26 120.0 . . ? C27 C26 C25 120.0(4) . . ? C27 C26 H26 120.0 . . ? C15 C16 C17 118.6(5) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? O29 C28 O30 122.8(4) . . ? O29 C28 C25 122.6(4) . . ? O30 C28 C25 114.6(4) . . ? O20 C18 C15 115.1(4) . . ? O19 C18 O20 123.2(5) . . ? O19 C18 C15 121.7(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O20 H20 O29 0.84(2) 1.84(2) 2.664(5) 171(7) 1_655 O30 H30 O19 0.84(2) 1.86(2) 2.697(5) 169(7) 3 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Co1 N5 C10 C9 -28.4(3) . . . . ? Co1 N5 C11 C12 -179.4(3) . . . . ? Co1 N5 C6 C7 -49.0(3) . . . . ? Co1 N8 C7 C6 -26.2(3) . . . . ? Cl3 Co1 N5 C10 -107.9(2) . . . . ? Cl3 Co1 N5 C11 13.7(3) . . . . ? Cl3 Co1 N5 C6 134.72(18) . . . . ? Cl3 Co1 N8 C21 13.6(2) . . . . ? Cl3 Co1 N8 C9 134.92(19) . . . 3_565 ? Cl3 Co1 N8 C7 -109.1(2) . . . . ? C22 C21 N8 Co1 176.2(2) . . . . ? C22 C21 N8 C9 61.4(4) . . . 3_565 ? C22 C21 N8 C7 -62.5(4) . . . . ? C22 C23 C24 C25 -0.1(5) . . . . ? C22 C27 C26 C25 0.6(6) . . . . ? N5 Co1 N5 C10 72.1(2) 3_565 . . . ? N5 Co1 N5 C11 -166.3(3) 3_565 . . . ? N5 Co1 N5 C6 -45.28(18) 3_565 . . . ? N5 Co1 N8 C21 122.6(2) . . . . ? N5 Co1 N8 C21 -95.6(2) 3_565 . . . ? N5 Co1 N8 C9 -116.1(2) . . . 3_565 ? N5 Co1 N8 C9 25.7(2) 3_565 . . 3_565 ? N5 Co1 N8 C7 141.7(2) 3_565 . . . ? N5 Co1 N8 C7 -0.1(2) . . . . ? N5 C10 C9 N8 55.3(4) . . . 3_565 ? C12 C17 C16 C15 -1.2(6) . . . . ? C12 C13 C14 C15 0.6(6) . . . . ? C10 N5 C11 C12 -59.6(4) . . . . ? C10 N5 C6 C7 -164.7(3) . . . . ? C11 N5 C10 C9 -149.6(3) . . . . ? C11 N5 C6 C7 70.5(4) . . . . ? C11 C12 C17 C16 179.2(4) . . . . ? C11 C12 C13 C14 -179.0(4) . . . . ? C21 C22 C23 C24 -179.6(3) . . . . ? C21 C22 C27 C26 179.3(3) . . . . ? C21 N8 C7 C6 -149.7(3) . . . . ? N8 Co1 N5 C10 143.2(2) . . . . ? N8 Co1 N5 C10 1.2(2) 3_565 . . . ? N8 Co1 N5 C11 -95.2(2) . . . . ? N8 Co1 N5 C11 122.8(2) 3_565 . . . ? N8 Co1 N5 C6 -116.2(2) 3_565 . . . ? N8 Co1 N5 C6 25.8(2) . . . . ? N8 Co1 N8 C21 -166.4(2) 3_565 . . . ? N8 Co1 N8 C9 -45.08(19) 3_565 . . 3_565 ? N8 Co1 N8 C7 70.9(2) 3_565 . . . ? N8 C7 C6 N5 52.3(4) . . . . ? C9 N8 C7 C6 84.6(4) 3_565 . . . ? C23 C22 C21 N8 94.5(4) . . . . ? C23 C22 C27 C26 -2.2(6) . . . . ? C23 C24 C25 C26 -1.5(5) . . . . ? C23 C24 C25 C28 178.5(3) . . . . ? C24 C25 C26 C27 1.2(5) . . . . ? C24 C25 C28 O29 -176.2(4) . . . . ? C24 C25 C28 O30 3.5(5) . . . . ? C17 C12 C11 N5 -90.0(4) . . . . ? C17 C12 C13 C14 1.2(6) . . . . ? C6 N5 C10 C9 84.6(3) . . . . ? C6 N5 C11 C12 65.0(4) . . . . ? C27 C22 C21 N8 -87.0(4) . . . . ? C27 C22 C23 C24 1.9(5) . . . . ? C13 C12 C11 N5 90.2(5) . . . . ? C13 C12 C17 C16 -1.0(6) . . . . ? C14 C15 C16 C17 3.1(7) . . . . ? C14 C15 C18 O20 8.6(6) . . . . ? C14 C15 C18 O19 -169.3(4) . . . . ? C26 C25 C28 O29 3.8(5) . . . . ? C26 C25 C28 O30 -176.5(3) . . . . ? C16 C15 C14 C13 -2.9(7) . . . . ? C16 C15 C18 O20 -171.5(4) . . . . ? C16 C15 C18 O19 10.6(6) . . . . ? C28 C25 C26 C27 -178.8(3) . . . . ? C18 C15 C14 C13 177.0(4) . . . . ? C18 C15 C16 C17 -176.8(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 967732' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 _audit_creation_date 2013-08-29 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:59:47, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.5(C168 H192 Cl4 Cu8 N16 O36), 0.25(Cl16 Cu4), 5(H2O)' _chemical_formula_sum 'C84 H106 Cl6 Cu5 N8 O23' _chemical_formula_weight 2126.17 _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 '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' 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' _space_group_crystal_system orthorhombic _space_group_IT_number 63 _space_group_name_H-M_alt 'C m c m' _space_group_name_Hall '-C 2c 2' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 'x, -y, -z' 4 '-x, y, -z+1/2' 5 'x+1/2, y+1/2, z' 6 '-x+1/2, -y+1/2, z+1/2' 7 'x+1/2, -y+1/2, -z' 8 '-x+1/2, y+1/2, -z+1/2' 9 '-x, -y, -z' 10 'x, y, -z-1/2' 11 '-x, y, z' 12 'x, -y, z-1/2' 13 '-x+1/2, -y+1/2, -z' 14 'x+1/2, y+1/2, -z-1/2' 15 '-x+1/2, y+1/2, z' 16 'x+1/2, -y+1/2, z-1/2' _cell_length_a 35.258(5) _cell_length_b 8.7597(15) _cell_length_c 29.409(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9083(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2017 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 20.261 _cell_measurement_theta_min 2.396 _exptl_absorpt_coefficient_mu 1.405 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6829 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0737 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.9153. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 4388 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1010 _diffrn_reflns_av_unetI/netI 0.0790 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 30080 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_min 2.49 _diffrn_ambient_temperature 123 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed tube' _diffrn_standards_number 0 _reflns_number_gt 3347 _reflns_number_total 5579 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XLMP, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 1.930 _refine_diff_density_min -1.419 _refine_diff_density_rms 0.126 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 409 _refine_ls_number_reflns 5579 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.1302 _refine_ls_R_factor_gt 0.0754 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1078P)^2^+57.9423P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1963 _refine_ls_wR_factor_ref 0.2311 _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. Structure model contained considerable disorder in the macrocyclic ring, coordinating ethanol molecule and tetrachlorocuprate anion. Disorder involving two conformations split across a symmetry site was modelled by including the entire (eg, macrocycle) moiety within the asymmetric unit and using PART -1 commands to prevent addition of nonsensical bonding within the connectivity table, and to allow modelling of riding hydrogen atoms using standard HFIX commands. DFIX restraints were applied in several instances to ensure chemically sensible bond lengths for hydrogen atoms which could not be attached using HFIX commands, for the Ar-CH2-N hydrogen atoms (which were located from Fourier residuals and modelled in PART 0 to avoid connectivity problems for the well-ordered aromatic rings) and hydrogen atoms attached to the disordered ethanol molecule. ISOR restraints were applied where neccesary to avoid unreasonable Ueq values and the emergence of non-positive definites. Lattice water molecules were modelled without hydrogen atoms due to the low occupancy of the unique sites and the presence of nearby symmetry elements, making assumption of hydrogen positions nonsensical, however these hydrogen atoms were included in the chemical formula to allow accurate determinations of density and absorption coefficient. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, {H40A,H40B} of C40, {H10A,H10B} of C10, {H13A,H13B} of C13, {H11A,H11B} of C11, {H14A,H14B} of C14, {H18A,H18B} of C18, {H2A,H2B} of C2, {H19A,H19B} of C19, {H16A,H16B} of C16, All N(H,H,H,H,H) groups At 1.5 times of: {H41A,H41B} of C40 2. Restrained distances C9-H9A 0.99 with sigma of 0.02 C9-H9B 0.99 with sigma of 0.02 C20-H20B 0.99 with sigma of 0.02 C20-H20A 0.99 with sigma of 0.02 H37-O37 0.84 with sigma of 0.02 H41A_$2-H41A 1.6 with sigma of 0.02 H41A_$2-H41B 1.6 with sigma of 0.02 H41B-H41A 1.6 with sigma of 0.02 H41A_$2-C41 0.99 with sigma of 0.02 H41A-C41 0.99 with sigma of 0.02 H41B-C41 0.99 with sigma of 0.02 H41B-C40 2 with sigma of 0.02 H41A_$2-C40 2 with sigma of 0.02 H41A-C40_$2 2 with sigma of 0.02 H40-O39 0.84 with sigma of 0.02 O40-H40 0.84 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(N17) \\sim Ueq, Uanis(N12) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(Cl5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(O40) \\sim Ueq: with sigma of 0.0001 and sigma for terminal atoms of 0.0002 4. Others Fixed Sof: Cu3(0.25) Cl7(0.25) Cl8(0.25) O40(0.16667) C13(0.5) H13A(0.5) H13B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C2(0.5) H2A(0.5) H2B(0.5) C14(0.5) H14A(0.5) H14B(0.5) C18(0.5) H18A(0.5) H18B(0.5) C19(0.5) H19A(0.5) H19B(0.5) C16(0.5) H16A(0.5) H16B(0.5) Cl5(0.25) Cl6(0.25) C10(0.5) H10A(0.5) H10B(0.5) N12(0.5) N15(0.5) N17(0.5) N9(0.5) O44(0.41666) O43(0.83333) O39(0.3333) C40(0.5) H40A(0.5) H40B(0.5) H40(0.5) 5.a Secondary CH2 refined with riding coordinates: C13(H13A,H13B), C11(H11A,H11B), C2(H2A,H2B), C14(H14A,H14B), C18(H18A,H18B), C19(H19A,H19B), C16(H16A,H16B), C10(H10A,H10B), C40(H40A,H40B) 5.b Aromatic/amide H refined with riding coordinates: C35(H35), C34(H34), C22(H22), C32(H32), C31(H31), C26(H26), C25(H25), C23(H23) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 Cu1 Cu 0.34038(3) 0.81973(10) 0.7500 0.0261(3) Uani 1 2 d S . . Cu2 Cu 0.5000 1.38164(11) 0.47290(4) 0.0474(4) Uani 1 2 d S . . Cl4 Cl 0.28296(5) 0.9600(2) 0.7500 0.0324(4) Uani 1 2 d S . . Cu3 Cu 0.5000 0.4363(2) 0.72914(8) 0.0416(5) Uani 0.50 2 d SP . . Cl7 Cl 0.5556(4) 0.4969(10) 0.7500 0.081(3) Uani 0.50 2 d SP . . O38 O 0.29174(14) 0.0272(5) 0.55626(14) 0.0502(12) Uani 1 1 d . . . Cl8 Cl 0.5000 0.1854(5) 0.7256(3) 0.080(2) Uani 0.50 2 d SP . . O28 O 0.46140(16) 1.2929(5) 0.51268(17) 0.0575(14) Uani 1 1 d . . . C9 C 0.29760(15) 0.6460(6) 0.67689(18) 0.0280(12) Uani 1 1 d D A -1 O37 O 0.2971(2) 0.1999(6) 0.50147(15) 0.0735(18) Uani 1 1 d D . . C35 C 0.28412(16) 0.3754(7) 0.65305(18) 0.0334(13) Uani 1 1 d . A . H35 H 0.2764 0.3550 0.6834 0.040 Uiso 1 1 calc R . . C36 C 0.29419(19) 0.1623(8) 0.5429(2) 0.0409(15) Uani 1 1 d . . . C33 C 0.29385(18) 0.2873(7) 0.57676(19) 0.0381(14) Uani 1 1 d . A . C30 C 0.29551(15) 0.5213(7) 0.64133(18) 0.0293(12) Uani 1 1 d . . . C34 C 0.28382(16) 0.2585(7) 0.62129(18) 0.0332(13) Uani 1 1 d . . . H34 H 0.2767 0.1583 0.6302 0.040 Uiso 1 1 calc R A . O29 O 0.46111(18) 1.5016(5) 0.44182(17) 0.0668(16) Uani 1 1 d . . . C24 C 0.4248(2) 1.2863(8) 0.5803(3) 0.055(2) Uani 1 1 d . . . C20 C 0.3563(2) 1.0505(8) 0.6785(3) 0.057(2) Uani 1 1 d D A -1 O40 O 0.5000 1.226(5) 0.4220(16) 0.043(12) Uani 0.33 2 d SPDU . 2 C22 C 0.3815(3) 1.0880(11) 0.5983(3) 0.077(3) Uani 1 1 d . A . H22 H 0.3660 1.0052 0.5887 0.092 Uiso 1 1 calc R . . C27 C 0.4512(2) 1.3640(8) 0.5472(3) 0.056(2) Uani 1 1 d . . . C32 C 0.3039(3) 0.4333(8) 0.5644(2) 0.060(2) Uani 1 1 d . . . H32 H 0.3103 0.4548 0.5337 0.072 Uiso 1 1 calc R A . C41 C 0.5000 0.9776(12) 0.3819(5) 0.084(4) Uani 1 2 d SD . . C31 C 0.3047(2) 0.5498(8) 0.5966(2) 0.0525(19) Uani 1 1 d . A . H31 H 0.3117 0.6501 0.5876 0.063 Uiso 1 1 calc R . . C21 C 0.3810(2) 1.1327(8) 0.6436(3) 0.054(2) Uani 1 1 d . . . C26 C 0.4028(2) 1.2531(7) 0.6567(3) 0.070(3) Uani 1 1 d . A . H26 H 0.4031 1.2833 0.6878 0.084 Uiso 1 1 calc R . . C25 C 0.4248(2) 1.3324(7) 0.6254(3) 0.065(2) Uani 1 1 d . . . H25 H 0.4397 1.4172 0.6347 0.078 Uiso 1 1 calc R A . C23 C 0.4039(3) 1.1608(10) 0.5670(3) 0.076(3) Uani 1 1 d . . . H23 H 0.4050 1.1253 0.5365 0.091 Uiso 1 1 calc R A . C13 C 0.3501(3) 0.5225(12) 0.7186(4) 0.026(2) Uani 0.50 1 d P A -1 H13A H 0.3775 0.5324 0.7253 0.031 Uiso 0.50 1 calc PR A -1 H13B H 0.3465 0.4341 0.6981 0.031 Uiso 0.50 1 calc PR A -1 C11 C 0.3647(4) 0.7101(19) 0.6593(4) 0.035(3) Uani 0.50 1 d P A -1 H11A H 0.3765 0.6181 0.6459 0.042 Uiso 0.50 1 calc PR A -1 H11B H 0.3515 0.7667 0.6348 0.042 Uiso 0.50 1 calc PR A -1 C2 C 0.3754(5) 0.7942(19) 0.8376(6) 0.042(4) Uani 0.50 1 d P A -1 H2A H 0.3574 0.8140 0.8627 0.050 Uiso 0.50 1 calc PR A -1 H2B H 0.4014 0.7961 0.8504 0.050 Uiso 0.50 1 calc PR A -1 C14 C 0.3285(3) 0.4966(10) 0.7623(3) 0.025(3) Uani 0.50 1 d P A -1 H14A H 0.3015 0.4763 0.7554 0.030 Uiso 0.50 1 calc PR A -1 H14B H 0.3389 0.4066 0.7783 0.030 Uiso 0.50 1 calc PR A -1 C18 C 0.4101(4) 0.9278(16) 0.7788(5) 0.045(3) Uani 0.50 1 d P A -1 H18A H 0.4287 0.9799 0.7987 0.054 Uiso 0.50 1 calc PR A -1 H18B H 0.4196 0.8237 0.7724 0.054 Uiso 0.50 1 calc PR A -1 C19 C 0.4062(4) 1.0156(16) 0.7344(5) 0.053(5) Uani 0.50 1 d P A -1 H19A H 0.3971 1.1209 0.7399 0.064 Uiso 0.50 1 calc PR A -1 H19B H 0.4307 1.0200 0.7180 0.064 Uiso 0.50 1 calc PR A -1 C16 C 0.3676(3) 0.6358(14) 0.8180(5) 0.034(3) Uani 0.50 1 d P A -1 H16A H 0.3888 0.6055 0.7979 0.041 Uiso 0.50 1 calc PR A -1 H16B H 0.3661 0.5607 0.8431 0.041 Uiso 0.50 1 calc PR A -1 Cl5 Cl 0.4420(4) 0.4436(12) 0.7500 0.110(4) Uani 0.50 2 d SPU . . Cl6 Cl 0.5131(2) 0.6429(7) 0.6791(3) 0.065(3) Uani 0.25 1 d P . . C10 C 0.3946(4) 0.8095(15) 0.6806(6) 0.039(3) Uani 0.50 1 d P A -1 H10A H 0.4117 0.7460 0.6994 0.047 Uiso 0.50 1 calc PR A -1 H10B H 0.4099 0.8583 0.6564 0.047 Uiso 0.50 1 calc PR A -1 N12 N 0.3362(6) 0.663(2) 0.6962(6) 0.021(3) Uani 0.50 1 d PU A -1 N15 N 0.3316(6) 0.634(2) 0.7917(6) 0.026(4) Uani 0.50 1 d P A -1 N17 N 0.3719(7) 0.917(3) 0.8034(7) 0.029(5) Uani 0.50 1 d PU A -1 N9 N 0.3776(8) 0.925(4) 0.7084(7) 0.032(5) Uani 0.50 1 d P A -1 H9A H 0.2952(17) 0.743(4) 0.6604(17) 0.038 Uiso 1 1 d D . . H9B H 0.2788(13) 0.634(7) 0.7014(15) 0.038 Uiso 1 1 d D . . H20A H 0.3485(18) 1.123(6) 0.7023(16) 0.038 Uiso 1 1 d D . . H20B H 0.3334(11) 1.016(7) 0.6621(18) 0.038 Uiso 1 1 d D . . H37 H 0.2987(18) 0.121(4) 0.4860(18) 0.038 Uiso 1 1 d D . . O44 O 0.5000 0.8512(17) 0.7314(5) 0.166(8) Uani 0.83 2 d SP . . O43 O 0.3932(4) 0.7372(19) 0.5572(4) 0.183(6) Uani 0.83 1 d P . . O39 O 0.4847(6) 1.2104(17) 0.4204(7) 0.032(3) Uani 0.33 1 d PD . 1 C40 C 0.4885(5) 1.0805(18) 0.4189(6) 0.078(8) Uani 0.50 1 d PD . . H40A H 0.4605 1.0826 0.4187 0.094 Uiso 0.50 1 calc PR . 2 H40B H 0.4962 1.0303 0.4476 0.094 Uiso 0.50 1 calc PR . 2 H41A H 0.5225(3) 0.906(3) 0.3774(11) 0.118 Uiso 1 1 d D . . H41B H 0.5000 1.042(4) 0.3535(8) 0.118 Uiso 1 2 d SD . . H40 H 0.492(3) 1.246(10) 0.3956(14) 0.02(3) Uiso 0.50 1 d PD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0168(5) 0.0213(4) 0.0402(5) 0.000 0.000 0.0036(3) Cu2 0.0849(10) 0.0232(5) 0.0340(6) 0.0173(4) 0.000 0.000 Cl4 0.0200(10) 0.0334(9) 0.0438(11) 0.000 0.000 0.0101(7) Cu3 0.0388(13) 0.0323(10) 0.0536(12) -0.0012(9) 0.000 0.000 Cl7 0.022(4) 0.041(5) 0.181(8) 0.000 0.000 -0.007(4) O38 0.062(3) 0.057(3) 0.032(2) -0.009(2) 0.006(2) -0.019(2) Cl8 0.060(3) 0.028(2) 0.150(6) -0.001(3) 0.000 0.000 O28 0.087(4) 0.032(2) 0.053(3) 0.017(2) 0.001(3) -0.009(2) C9 0.018(3) 0.038(3) 0.028(3) 0.001(2) 0.001(2) 0.008(2) O37 0.144(6) 0.056(3) 0.021(2) -0.009(2) 0.005(3) 0.015(3) C35 0.024(3) 0.055(4) 0.021(3) -0.010(2) 0.006(2) -0.013(3) C36 0.041(4) 0.055(4) 0.027(3) -0.004(3) 0.003(3) 0.004(3) C33 0.038(4) 0.052(4) 0.024(3) -0.004(3) 0.001(3) 0.003(3) C30 0.020(3) 0.046(3) 0.022(3) -0.004(2) 0.000(2) 0.010(2) C34 0.028(3) 0.046(3) 0.026(3) -0.010(2) 0.001(2) -0.012(2) O29 0.107(5) 0.038(3) 0.055(3) 0.017(2) -0.024(3) 0.009(3) C24 0.058(5) 0.036(3) 0.072(5) 0.034(3) 0.001(4) 0.002(3) C20 0.035(4) 0.038(4) 0.097(6) 0.026(4) 0.007(4) 0.014(3) O40 0.043(12) 0.043(12) 0.043(12) 0.0001(11) 0.000 0.000 C22 0.071(6) 0.081(6) 0.079(6) 0.052(5) -0.036(5) -0.028(5) C27 0.079(6) 0.037(4) 0.052(4) 0.029(3) -0.003(4) -0.002(3) C32 0.110(7) 0.051(4) 0.020(3) 0.001(3) 0.011(4) 0.011(4) C41 0.123(12) 0.032(5) 0.099(10) -0.012(6) 0.000 0.000 C31 0.090(6) 0.038(3) 0.030(3) 0.007(3) 0.007(3) 0.011(3) C21 0.037(4) 0.039(4) 0.086(6) 0.030(4) 0.013(4) 0.015(3) C26 0.087(6) 0.022(3) 0.102(6) 0.002(3) 0.055(5) 0.007(3) C25 0.080(6) 0.026(3) 0.090(6) 0.004(3) 0.045(5) 0.003(3) C23 0.087(7) 0.084(6) 0.057(5) 0.041(4) -0.021(5) -0.028(5) C13 0.022(6) 0.033(6) 0.023(5) 0.000(4) 0.000(5) 0.003(4) C11 0.026(7) 0.044(8) 0.034(7) 0.020(7) 0.011(5) 0.011(6) C2 0.034(10) 0.039(8) 0.053(10) -0.019(8) -0.023(8) 0.008(8) C14 0.037(6) 0.017(4) 0.022(7) -0.002(3) -0.001(4) 0.002(4) C18 0.023(7) 0.034(7) 0.077(10) -0.017(7) -0.008(7) -0.005(5) C19 0.028(7) 0.033(6) 0.099(17) 0.009(7) -0.007(7) -0.014(5) C16 0.019(6) 0.041(7) 0.041(7) 0.002(6) -0.007(5) 0.009(5) Cl5 0.025(4) 0.069(7) 0.234(9) 0.000 0.000 0.007(6) Cl6 0.088(8) 0.033(3) 0.075(5) -0.013(3) -0.015(4) 0.000(3) C10 0.020(8) 0.031(6) 0.066(10) 0.010(6) 0.011(7) 0.005(6) N12 0.017(6) 0.024(6) 0.022(7) 0.010(5) -0.001(5) 0.005(5) N15 0.024(8) 0.026(8) 0.029(9) -0.009(6) 0.001(7) 0.003(5) N17 0.020(8) 0.033(6) 0.033(9) -0.017(7) 0.001(7) 0.014(6) N9 0.023(10) 0.039(7) 0.033(10) 0.015(8) -0.016(7) 0.005(6) O44 0.28(2) 0.107(11) 0.111(13) -0.001(8) 0.000 0.000 O43 0.196(14) 0.206(14) 0.148(11) 0.025(11) 0.074(10) 0.029(11) O39 0.040(10) 0.017(7) 0.038(8) 0.009(5) 0.007(9) -0.005(7) C40 0.10(2) 0.058(9) 0.078(10) 0.002(8) 0.010(10) -0.039(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 Cl4 2.368(2) . ? Cu1 N12 2.10(2) . ? Cu1 N12 2.10(2) 10_557 ? Cu1 N15 2.06(2) . ? Cu1 N15 2.06(2) 10_557 ? Cu1 N17 2.10(3) . ? Cu1 N17 2.10(3) 10_557 ? Cu1 N9 2.02(3) . ? Cu1 N9 2.02(3) 10_557 ? Cu2 Cu2 2.616(2) 9_686 ? Cu2 O28 1.956(5) . ? Cu2 O28 1.956(5) 11_655 ? Cu2 O29 1.954(5) . ? Cu2 O29 1.954(5) 11_655 ? Cu2 O40 2.02(4) . ? Cu2 O39 2.22(2) 11_655 ? Cu2 O39 2.22(2) . ? Cu3 Cu3 1.227(5) 10_557 ? Cu3 Cl7 2.122(14) . ? Cu3 Cl7 2.122(13) 11_655 ? Cu3 Cl8 2.200(5) . ? Cu3 Cl8 2.569(6) 10_557 ? Cu3 Cl5 2.135(15) 11_655 ? Cu3 Cl5 2.135(15) . ? Cu3 Cl6 2.377(8) 11_655 ? Cu3 Cl6 2.377(8) . ? Cl7 Cu3 2.122(13) 10_557 ? Cl7 Cl5 0.474(14) 11_655 ? O38 C36 1.249(8) . ? Cl8 Cu3 2.569(6) 10_557 ? Cl8 Cl8 1.435(15) 10_557 ? O28 C27 1.244(9) . ? C9 C30 1.515(8) . ? C9 N12 1.48(2) . ? C9 H9A 0.99(2) . ? C9 H9B 0.98(2) . ? O37 C36 1.268(8) . ? O37 H37 0.83(2) . ? C35 H35 0.9500 . ? C35 C30 1.383(8) . ? C35 C34 1.386(7) . ? C36 C33 1.480(8) . ? C33 C34 1.380(8) . ? C33 C32 1.375(10) . ? C30 C31 1.377(8) . ? C34 H34 0.9500 . ? O29 C27 1.271(9) 3_586 ? C24 C27 1.508(10) . ? C24 C25 1.385(11) . ? C24 C23 1.381(11) . ? C20 C21 1.527(10) . ? C20 N9 1.60(3) . ? C20 H20A 0.99(2) . ? C20 H20B 0.99(2) . ? O40 C40 1.34(4) 11_655 ? O40 C40 1.34(4) . ? O40 H40 0.85(2) . ? C22 H22 0.9500 . ? C22 C21 1.389(12) . ? C22 C23 1.368(11) . ? C27 O29 1.271(9) 3_586 ? C32 H32 0.9500 . ? C32 C31 1.393(9) . ? C41 C40 1.469(18) . ? C41 C40 1.469(18) 11_655 ? C41 H41A 1.017(11) . ? C41 H41B 1.009(19) . ? C31 H31 0.9500 . ? C21 C26 1.363(11) . ? C26 H26 0.9500 . ? C26 C25 1.390(10) . ? C25 H25 0.9500 . ? C23 H23 0.9500 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.509(13) . ? C13 N12 1.484(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C10 1.50(2) . ? C11 N12 1.533(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C16 1.528(18) . ? C2 N17 1.48(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 N15 1.485(16) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 C19 1.522(18) . ? C18 N17 1.53(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 N9 1.49(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 N15 1.48(2) . ? Cl5 Cu3 2.135(15) 10_557 ? Cl5 Cl7 0.474(14) 11_655 ? Cl6 Cl6 0.921(16) 11_655 ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 N9 1.43(3) . ? O39 O39 1.08(4) 11_655 ? O39 C40 1.48(2) 11_655 ? O39 C40 1.15(2) . ? O39 H40 0.83(2) . ? C40 O39 1.48(2) 11_655 ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? 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 N12 Cu1 Cl4 106.1(6) 10_557 . ? N12 Cu1 Cl4 106.1(6) . . ? N12 Cu1 N12 98.0(7) . 10_557 ? N12 Cu1 N17 74.9(8) . 10_557 ? N12 Cu1 N17 74.9(8) 10_557 . ? N12 Cu1 N17 149.9(9) 10_557 10_557 ? N12 Cu1 N17 149.9(9) . . ? N15 Cu1 Cl4 106.4(6) 10_557 . ? N15 Cu1 Cl4 106.4(6) . . ? N15 Cu1 N12 12.9(5) . 10_557 ? N15 Cu1 N12 85.6(5) 10_557 10_557 ? N15 Cu1 N12 85.6(5) . . ? N15 Cu1 N12 12.9(5) 10_557 . ? N15 Cu1 N15 73.0(8) 10_557 . ? N15 Cu1 N17 87.5(8) 10_557 10_557 ? N15 Cu1 N17 147.5(9) . 10_557 ? N15 Cu1 N17 147.5(9) 10_557 . ? N15 Cu1 N17 87.5(8) . . ? N17 Cu1 Cl4 103.9(7) 10_557 . ? N17 Cu1 Cl4 103.9(7) . . ? N17 Cu1 N17 96.5(13) 10_557 . ? N9 Cu1 Cl4 108.6(8) 10_557 . ? N9 Cu1 Cl4 108.6(8) . . ? N9 Cu1 N12 83.5(9) . . ? N9 Cu1 N12 143.3(9) 10_557 . ? N9 Cu1 N12 83.5(9) 10_557 10_557 ? N9 Cu1 N12 143.3(9) . 10_557 ? N9 Cu1 N15 95.6(9) 10_557 . ? N9 Cu1 N15 145.0(10) . . ? N9 Cu1 N15 95.6(9) . 10_557 ? N9 Cu1 N15 145.0(10) 10_557 10_557 ? N9 Cu1 N17 85.6(6) 10_557 10_557 ? N9 Cu1 N17 85.6(6) . . ? N9 Cu1 N17 11.1(10) 10_557 . ? N9 Cu1 N17 11.1(10) . 10_557 ? N9 Cu1 N9 74.7(12) 10_557 . ? O28 Cu2 Cu2 87.15(15) 11_655 9_686 ? O28 Cu2 Cu2 87.15(15) . 9_686 ? O28 Cu2 O28 88.2(3) 11_655 . ? O28 Cu2 O40 100.1(10) 11_655 . ? O28 Cu2 O40 100.1(10) . . ? O28 Cu2 O39 88.7(4) . . ? O28 Cu2 O39 108.5(5) 11_655 . ? O28 Cu2 O39 108.5(5) . 11_655 ? O28 Cu2 O39 88.7(4) 11_655 11_655 ? O29 Cu2 Cu2 81.88(16) . 9_686 ? O29 Cu2 Cu2 81.88(16) 11_655 9_686 ? O29 Cu2 O28 90.3(2) 11_655 11_655 ? O29 Cu2 O28 90.3(2) . . ? O29 Cu2 O28 169.0(2) 11_655 . ? O29 Cu2 O28 169.0(2) . 11_655 ? O29 Cu2 O29 89.1(3) 11_655 . ? O29 Cu2 O40 90.9(10) 11_655 . ? O29 Cu2 O40 90.9(10) . . ? O29 Cu2 O39 82.4(5) 11_655 11_655 ? O29 Cu2 O39 82.4(5) . . ? O29 Cu2 O39 102.1(5) . 11_655 ? O29 Cu2 O39 102.1(4) 11_655 . ? O40 Cu2 Cu2 169.8(13) . 9_686 ? O40 Cu2 O39 14.2(5) . . ? O40 Cu2 O39 14.2(5) . 11_655 ? O39 Cu2 Cu2 163.7(5) . 9_686 ? O39 Cu2 Cu2 163.7(5) 11_655 9_686 ? O39 Cu2 O39 28.2(10) . 11_655 ? Cu3 Cu3 Cl7 73.20(13) 10_557 . ? Cu3 Cu3 Cl7 73.20(13) 10_557 11_655 ? Cu3 Cu3 Cl8 92.7(2) 10_557 . ? Cu3 Cu3 Cl8 58.80(16) 10_557 10_557 ? Cu3 Cu3 Cl5 73.30(14) 10_557 11_655 ? Cu3 Cu3 Cl5 73.30(14) 10_557 . ? Cu3 Cu3 Cl6 128.21(18) 10_557 11_655 ? Cu3 Cu3 Cl6 128.21(18) 10_557 . ? Cl7 Cu3 Cl7 135.0(4) 11_655 . ? Cl7 Cu3 Cl8 93.7(2) 11_655 10_557 ? Cl7 Cu3 Cl8 105.3(3) . . ? Cl7 Cu3 Cl8 93.7(2) . 10_557 ? Cl7 Cu3 Cl8 105.3(3) 11_655 . ? Cl7 Cu3 Cl5 12.8(4) 11_655 . ? Cl7 Cu3 Cl5 142.6(2) . . ? Cl7 Cu3 Cl5 12.8(4) . 11_655 ? Cl7 Cu3 Cl5 142.6(2) 11_655 11_655 ? Cl7 Cu3 Cl6 79.0(3) 11_655 11_655 ? Cl7 Cu3 Cl6 99.6(3) . 11_655 ? Cl7 Cu3 Cl6 99.6(3) 11_655 . ? Cl7 Cu3 Cl6 79.0(3) . . ? Cl8 Cu3 Cl8 33.9(4) . 10_557 ? Cl8 Cu3 Cl6 137.0(3) . 11_655 ? Cl8 Cu3 Cl6 137.0(3) . . ? Cl5 Cu3 Cl8 92.5(3) . . ? Cl5 Cu3 Cl8 92.5(3) 11_655 . ? Cl5 Cu3 Cl8 82.9(3) 11_655 10_557 ? Cl5 Cu3 Cl8 82.9(3) . 10_557 ? Cl5 Cu3 Cl5 146.4(3) . 11_655 ? Cl5 Cu3 Cl6 88.2(3) 11_655 . ? Cl5 Cu3 Cl6 109.9(3) . . ? Cl5 Cu3 Cl6 109.9(3) 11_655 11_655 ? Cl5 Cu3 Cl6 88.2(3) . 11_655 ? Cl6 Cu3 Cl8 166.4(2) . 10_557 ? Cl6 Cu3 Cl8 166.4(2) 11_655 10_557 ? Cl6 Cu3 Cl6 22.3(4) . 11_655 ? Cu3 Cl7 Cu3 33.6(3) 10_557 . ? Cl5 Cl7 Cu3 85(3) 11_655 10_557 ? Cl5 Cl7 Cu3 85(3) 11_655 . ? Cu3 Cl8 Cu3 28.49(13) . 10_557 ? Cl8 Cl8 Cu3 58.80(16) 10_557 10_557 ? Cl8 Cl8 Cu3 87.3(2) 10_557 . ? C27 O28 Cu2 119.4(5) . . ? C30 C9 H9A 106(3) . . ? C30 C9 H9B 113(4) . . ? N12 C9 C30 112.6(9) . . ? N12 C9 H9A 100(4) . . ? N12 C9 H9B 110(4) . . ? H9A C9 H9B 113(5) . . ? C36 O37 H37 109(5) . . ? C30 C35 H35 119.4 . . ? C30 C35 C34 121.1(5) . . ? C34 C35 H35 119.4 . . ? O38 C36 O37 123.6(6) . . ? O38 C36 C33 119.3(5) . . ? O37 C36 C33 117.0(6) . . ? C34 C33 C36 120.3(6) . . ? C32 C33 C36 120.6(5) . . ? C32 C33 C34 119.1(6) . . ? C35 C30 C9 120.6(5) . . ? C31 C30 C9 121.1(5) . . ? C31 C30 C35 118.3(5) . . ? C35 C34 H34 119.9 . . ? C33 C34 C35 120.1(6) . . ? C33 C34 H34 119.9 . . ? C27 O29 Cu2 125.0(5) 3_586 . ? C25 C24 C27 119.1(7) . . ? C23 C24 C27 120.4(8) . . ? C23 C24 C25 120.2(7) . . ? C21 C20 N9 115.3(12) . . ? C21 C20 H20A 109(4) . . ? C21 C20 H20B 106(4) . . ? N9 C20 H20A 101(4) . . ? N9 C20 H20B 116(4) . . ? H20A C20 H20B 109(5) . . ? Cu2 O40 H40 123(8) . . ? C40 O40 Cu2 134(3) 11_655 . ? C40 O40 Cu2 134(3) . . ? C40 O40 C40 35.0(19) . 11_655 ? C40 O40 H40 104(7) 11_655 . ? C40 O40 H40 92(7) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C23 C22 C21 121.4(8) . . ? O28 C27 O29 126.2(7) . 3_586 ? O28 C27 C24 118.7(7) . . ? O29 C27 C24 115.1(7) 3_586 . ? C33 C32 H32 119.8 . . ? C33 C32 C31 120.4(6) . . ? C31 C32 H32 119.8 . . ? C40 C41 C40 31.9(14) 11_655 . ? C40 C41 H41A 133.3(19) . . ? C40 C41 H41A 105.0(13) 11_655 . ? C40 C41 H41B 106(2) . . ? C40 C41 H41B 106(2) 11_655 . ? H41A C41 H41B 103.7(17) . . ? C30 C31 C32 120.8(6) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C22 C21 C20 121.3(8) . . ? C26 C21 C20 119.8(8) . . ? C26 C21 C22 118.9(7) . . ? C21 C26 H26 119.6 . . ? C21 C26 C25 120.9(8) . . ? C25 C26 H26 119.6 . . ? C24 C25 C26 119.3(8) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C24 C23 H23 120.4 . . ? C22 C23 C24 119.3(9) . . ? C22 C23 H23 120.4 . . ? H13A C13 H13B 108.2 . . ? C14 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? N12 C13 H13A 109.7 . . ? N12 C13 H13B 109.7 . . ? N12 C13 C14 109.7(10) . . ? H11A C11 H11B 108.3 . . ? C10 C11 H11A 109.9 . . ? C10 C11 H11B 109.9 . . ? C10 C11 N12 108.7(13) . . ? N12 C11 H11A 109.9 . . ? N12 C11 H11B 109.9 . . ? H2A C2 H2B 107.8 . . ? C16 C2 H2A 109.0 . . ? C16 C2 H2B 109.0 . . ? N17 C2 H2A 109.0 . . ? N17 C2 H2B 109.0 . . ? N17 C2 C16 113.0(15) . . ? C13 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N15 C14 C13 109.7(11) . . ? N15 C14 H14A 109.7 . . ? N15 C14 H14B 109.7 . . ? H18A C18 H18B 108.1 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? C19 C18 N17 110.8(14) . . ? N17 C18 H18A 109.5 . . ? N17 C18 H18B 109.5 . . ? C18 C19 H19A 111.1 . . ? C18 C19 H19B 111.1 . . ? H19A C19 H19B 109.0 . . ? N9 C19 C18 103.4(13) . . ? N9 C19 H19A 111.1 . . ? N9 C19 H19B 111.1 . . ? C2 C16 H16A 109.4 . . ? C2 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N15 C16 C2 111.2(11) . . ? N15 C16 H16A 109.4 . . ? N15 C16 H16B 109.4 . . ? Cu3 Cl5 Cu3 33.4(3) 10_557 . ? Cl7 Cl5 Cu3 82(3) 11_655 . ? Cl7 Cl5 Cu3 82(3) 11_655 10_557 ? Cl6 Cl6 Cu3 78.83(19) 11_655 . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N9 C10 C11 110.6(15) . . ? N9 C10 H10A 109.5 . . ? N9 C10 H10B 109.5 . . ? C9 N12 Cu1 114.9(12) . . ? C9 N12 C13 112.8(12) . . ? C9 N12 C11 111.0(12) . . ? C13 N12 Cu1 100.6(10) . . ? C13 N12 C11 108.7(15) . . ? C11 N12 Cu1 108.2(12) . . ? C14 N15 Cu1 107.6(10) . . ? C16 N15 Cu1 99.9(11) . . ? C16 N15 C14 112.2(15) . . ? C2 N17 Cu1 104.9(17) . . ? C2 N17 C18 106.8(19) . . ? C18 N17 Cu1 97.9(12) . . ? C20 N9 Cu1 110.1(15) . . ? C19 N9 Cu1 111.8(14) . . ? C19 N9 C20 103.5(19) . . ? C10 N9 Cu1 107.2(18) . . ? C10 N9 C20 111.7(15) . . ? C10 N9 C19 113(2) . . ? Cu2 O39 H40 106(7) . . ? O39 O39 Cu2 75.9(5) 11_655 . ? O39 O39 C40 83.1(14) 11_655 . ? O39 O39 C40 50.3(10) 11_655 11_655 ? O39 O39 H40 73(7) 11_655 . ? C40 O39 Cu2 132.0(18) . . ? C40 O39 Cu2 112.7(15) 11_655 . ? C40 O39 C40 32.8(17) . 11_655 ? C40 O39 H40 94(6) 11_655 . ? C40 O39 H40 108(7) . . ? O40 C40 C41 123(2) . . ? O40 C40 O39 22.2(10) . 11_655 ? O40 C40 H40A 106.5 . . ? O40 C40 H40B 106.5 . . ? C41 C40 O39 108.6(15) . 11_655 ? C41 C40 H40A 106.5 . . ? C41 C40 H40B 106.5 . . ? O39 C40 O40 24.4(14) . . ? O39 C40 C41 132.2(17) . . ? O39 C40 O39 46.6(18) . 11_655 ? O39 C40 H40A 82.1 . . ? O39 C40 H40A 128.6 11_655 . ? O39 C40 H40B 98.1 11_655 . ? O39 C40 H40B 116.1 . . ? H40A C40 H40B 106.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O37 H37 O38 0.83(2) 1.82(3) 2.622(7) 165(6) 3_556 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu2 Cu2 O28 C27 -2.0(5) 9_686 . . . ? Cu2 Cu2 O29 C27 4.4(6) 9_686 . . 3_586 ? Cu2 Cu2 O40 C40 155(2) 9_686 . . 11_655 ? Cu2 Cu2 O40 C40 -155(2) 9_686 . . . ? Cu2 Cu2 O39 O39 149.2(15) 9_686 . . 11_655 ? Cu2 Cu2 O39 C40 -143.9(16) 9_686 . . . ? Cu2 Cu2 O39 C40 -175.7(10) 9_686 . . 11_655 ? Cu2 O28 C27 O29 6.1(11) . . . 3_586 ? Cu2 O28 C27 C24 -173.0(5) . . . . ? Cu2 O40 C40 C41 -163.8(11) . . . . ? Cu2 O40 C40 O39 -111(8) . . . 11_655 ? Cu2 O40 C40 O39 77(6) . . . . ? Cu2 O39 C40 O40 -60(7) . . . . ? Cu2 O39 C40 C41 -138.6(16) . . . . ? Cu2 O39 C40 O39 -64.0(16) . . . 11_655 ? Cl4 Cu1 N12 C9 -13.1(8) . . . . ? Cl4 Cu1 N12 C13 -134.6(9) . . . . ? Cl4 Cu1 N12 C11 111.5(11) . . . . ? Cl4 Cu1 N15 C14 107.2(11) . . . . ? Cl4 Cu1 N15 C16 -135.6(9) . . . . ? Cl4 Cu1 N17 C2 114.5(13) . . . . ? Cl4 Cu1 N17 C18 -135.7(12) . . . . ? Cl4 Cu1 N9 C20 -12.4(15) . . . . ? Cl4 Cu1 N9 C19 102.0(16) . . . . ? Cl4 Cu1 N9 C10 -134.1(12) . . . . ? Cu3 Cu3 Cl7 Cl5 88.5(10) 10_557 . . 11_655 ? Cu3 Cu3 Cl8 Cl8 0.000(3) 10_557 . . 10_557 ? Cu3 Cu3 Cl5 Cl7 87.6(10) 10_557 . . 11_655 ? Cu3 Cu3 Cl6 Cl6 -98.94(16) 10_557 . . 11_655 ? Cl7 Cu3 Cl7 Cu3 43.2(5) 11_655 . . 10_557 ? Cl7 Cu3 Cl7 Cl5 131.7(10) 11_655 . . 11_655 ? Cl7 Cu3 Cl8 Cu3 73.32(15) . . . 10_557 ? Cl7 Cu3 Cl8 Cu3 -73.32(15) 11_655 . . 10_557 ? Cl7 Cu3 Cl8 Cl8 -73.32(15) 11_655 . . 10_557 ? Cl7 Cu3 Cl8 Cl8 73.32(15) . . . 10_557 ? Cl7 Cu3 Cl5 Cu3 -87.6(10) 11_655 . . 10_557 ? Cl7 Cu3 Cl5 Cu3 -27.4(6) . . . 10_557 ? Cl7 Cu3 Cl5 Cl7 60.3(12) . . . 11_655 ? Cl7 Cu3 Cl6 Cl6 -22.8(2) 11_655 . . 11_655 ? Cl7 Cu3 Cl6 Cl6 -157.1(2) . . . 11_655 ? O38 C36 C33 C34 -12.2(10) . . . . ? O38 C36 C33 C32 167.1(7) . . . . ? Cl8 Cu3 Cl7 Cu3 -88.2(2) . . . 10_557 ? Cl8 Cu3 Cl7 Cu3 -55.82(18) 10_557 . . 10_557 ? Cl8 Cu3 Cl7 Cl5 32.7(10) 10_557 . . 11_655 ? Cl8 Cu3 Cl7 Cl5 0.3(11) . . . 11_655 ? Cl8 Cu3 Cl8 Cu3 0.000(5) 10_557 . . 10_557 ? Cl8 Cu3 Cl5 Cu3 59.48(17) 10_557 . . 10_557 ? Cl8 Cu3 Cl5 Cu3 92.1(2) . . . 10_557 ? Cl8 Cu3 Cl5 Cl7 147.1(10) 10_557 . . 11_655 ? Cl8 Cu3 Cl5 Cl7 179.7(10) . . . 11_655 ? Cl8 Cu3 Cl6 Cl6 144.4(10) 10_557 . . 11_655 ? Cl8 Cu3 Cl6 Cl6 102.2(2) . . . 11_655 ? O28 Cu2 O28 C27 85.3(6) 11_655 . . . ? O28 Cu2 O29 C27 91.4(6) . . . 3_586 ? O28 Cu2 O29 C27 9.4(16) 11_655 . . 3_586 ? O28 Cu2 O40 C40 20(2) 11_655 . . 11_655 ? O28 Cu2 O40 C40 -69.5(19) . . . 11_655 ? O28 Cu2 O40 C40 69.5(19) 11_655 . . . ? O28 Cu2 O40 C40 -20(2) . . . . ? O28 Cu2 O39 O39 -47.7(2) 11_655 . . 11_655 ? O28 Cu2 O39 O39 -135.42(18) . . . 11_655 ? O28 Cu2 O39 C40 19(2) 11_655 . . . ? O28 Cu2 O39 C40 -12.7(13) 11_655 . . 11_655 ? O28 Cu2 O39 C40 -100.4(12) . . . 11_655 ? O28 Cu2 O39 C40 -69(2) . . . . ? C9 C30 C31 C32 177.9(7) . . . . ? O37 C36 C33 C34 167.9(7) . . . . ? O37 C36 C33 C32 -12.8(10) . . . . ? C35 C30 C31 C32 -2.4(11) . . . . ? C36 C33 C34 C35 179.0(6) . . . . ? C36 C33 C32 C31 -178.0(7) . . . . ? C33 C32 C31 C30 0.0(12) . . . . ? C30 C9 N12 Cu1 -174.5(5) . . . . ? C30 C9 N12 C13 -60.0(13) . . . . ? C30 C9 N12 C11 62.3(14) . . . . ? C30 C35 C34 C33 -2.0(9) . . . . ? C34 C35 C30 C9 -176.9(5) . . . . ? C34 C35 C30 C31 3.4(9) . . . . ? C34 C33 C32 C31 1.3(12) . . . . ? O29 Cu2 O28 C27 3.0(15) 11_655 . . . ? O29 Cu2 O28 C27 -83.8(6) . . . . ? O29 Cu2 O29 C27 -77.6(7) 11_655 . . 3_586 ? O29 Cu2 O40 C40 111(2) 11_655 . . 11_655 ? O29 Cu2 O40 C40 -160(2) . . . 11_655 ? O29 Cu2 O40 C40 -111(2) . . . . ? O29 Cu2 O40 C40 160(2) 11_655 . . . ? O29 Cu2 O39 O39 46.69(19) 11_655 . . 11_655 ? O29 Cu2 O39 O39 134.1(2) . . . 11_655 ? O29 Cu2 O39 C40 113.6(19) 11_655 . . . ? O29 Cu2 O39 C40 81.7(12) 11_655 . . 11_655 ? O29 Cu2 O39 C40 -159(2) . . . . ? O29 Cu2 O39 C40 169.2(12) . . . 11_655 ? C20 C21 C26 C25 -178.3(7) . . . . ? O40 Cu2 O28 C27 -174.8(11) . . . . ? O40 Cu2 O29 C27 -168.4(11) . . . 3_586 ? O40 Cu2 O39 O39 8(7) . . . 11_655 ? O40 Cu2 O39 C40 43(7) . . . 11_655 ? O40 Cu2 O39 C40 75(7) . . . . ? C22 C21 C26 C25 1.3(12) . . . . ? C27 C24 C25 C26 -174.9(7) . . . . ? C27 C24 C23 C22 177.0(8) . . . . ? C32 C33 C34 C35 -0.4(10) . . . . ? C21 C20 N9 Cu1 -176.8(9) . . . . ? C21 C20 N9 C19 63.6(18) . . . . ? C21 C20 N9 C10 -58(2) . . . . ? C21 C22 C23 C24 -3.5(14) . . . . ? C21 C26 C25 C24 -1.0(12) . . . . ? C25 C24 C27 O28 154.7(7) . . . . ? C25 C24 C27 O29 -24.5(10) . . . 3_586 ? C25 C24 C23 C22 3.7(13) . . . . ? C23 C24 C27 O28 -18.7(11) . . . . ? C23 C24 C27 O29 162.0(8) . . . 3_586 ? C23 C24 C25 C26 -1.5(12) . . . . ? C23 C22 C21 C20 -179.4(8) . . . . ? C23 C22 C21 C26 1.0(12) . . . . ? C13 C14 N15 Cu1 26.7(14) . . . . ? C13 C14 N15 C16 -82.2(15) . . . . ? C11 C10 N9 Cu1 50.1(16) . . . . ? C11 C10 N9 C20 -71(2) . . . . ? C11 C10 N9 C19 173.5(15) . . . . ? C2 C16 N15 Cu1 50.7(14) . . . . ? C2 C16 N15 C14 164.4(14) . . . . ? C14 C13 N12 Cu1 52.0(11) . . . . ? C14 C13 N12 C9 -70.9(15) . . . . ? C14 C13 N12 C11 165.6(12) . . . . ? C18 C19 N9 Cu1 30.4(19) . . . . ? C18 C19 N9 C20 148.8(14) . . . . ? C18 C19 N9 C10 -90.4(19) . . . . ? C19 C18 N17 Cu1 55.0(14) . . . . ? C19 C18 N17 C2 163.1(14) . . . . ? C16 C2 N17 Cu1 18.2(18) . . . . ? C16 C2 N17 C18 -85(2) . . . . ? Cl5 Cu3 Cl7 Cu3 -88.5(10) 11_655 . . 10_557 ? Cl5 Cu3 Cl7 Cu3 27.4(6) . . . 10_557 ? Cl5 Cu3 Cl7 Cl5 115.9(13) . . . 11_655 ? Cl5 Cu3 Cl8 Cu3 73.39(14) 11_655 . . 10_557 ? Cl5 Cu3 Cl8 Cu3 -73.39(14) . . . 10_557 ? Cl5 Cu3 Cl8 Cl8 73.39(14) 11_655 . . 10_557 ? Cl5 Cu3 Cl8 Cl8 -73.39(14) . . . 10_557 ? Cl5 Cu3 Cl5 Cu3 -6.3(10) 11_655 . . 10_557 ? Cl5 Cu3 Cl5 Cl7 81.4(15) 11_655 . . 11_655 ? Cl5 Cu3 Cl6 Cl6 -14.9(2) . . . 11_655 ? Cl5 Cu3 Cl6 Cl6 -166.0(2) 11_655 . . 11_655 ? Cl6 Cu3 Cl7 Cu3 135.8(2) . . . 10_557 ? Cl6 Cu3 Cl7 Cu3 127.17(19) 11_655 . . 10_557 ? Cl6 Cu3 Cl7 Cl5 -135.7(11) . . . 11_655 ? Cl6 Cu3 Cl7 Cl5 -144.3(10) 11_655 . . 11_655 ? Cl6 Cu3 Cl8 Cu3 163.5(3) . . . 10_557 ? Cl6 Cu3 Cl8 Cu3 -163.5(3) 11_655 . . 10_557 ? Cl6 Cu3 Cl8 Cl8 163.5(3) . . . 10_557 ? Cl6 Cu3 Cl8 Cl8 -163.5(3) 11_655 . . 10_557 ? Cl6 Cu3 Cl5 Cu3 -130.9(2) 11_655 . . 10_557 ? Cl6 Cu3 Cl5 Cu3 -125.3(2) . . . 10_557 ? Cl6 Cu3 Cl5 Cl7 -37.7(11) . . . 11_655 ? Cl6 Cu3 Cl5 Cl7 -43.3(10) 11_655 . . 11_655 ? C10 C11 N12 Cu1 20.8(15) . . . . ? C10 C11 N12 C9 147.8(12) . . . . ? C10 C11 N12 C13 -87.6(16) . . . . ? N12 Cu1 N12 C9 96.3(10) 10_557 . . . ? N12 Cu1 N12 C13 -25.2(15) 10_557 . . . ? N12 Cu1 N12 C11 -139.0(7) 10_557 . . . ? N12 Cu1 N15 C14 -162(6) 10_557 . . . ? N12 Cu1 N15 C14 1.6(8) . . . . ? N12 Cu1 N15 C16 118.8(14) . . . . ? N12 Cu1 N15 C16 -45(5) 10_557 . . . ? N12 Cu1 N17 C2 -68(2) . . . . ? N12 Cu1 N17 C2 11.2(13) 10_557 . . . ? N12 Cu1 N17 C18 121.0(15) 10_557 . . . ? N12 Cu1 N17 C18 41(2) . . . . ? N12 Cu1 N9 C20 -173.0(7) 10_557 . . . ? N12 Cu1 N9 C20 92.4(14) . . . . ? N12 Cu1 N9 C19 -59(3) 10_557 . . . ? N12 Cu1 N9 C19 -153.1(18) . . . . ? N12 Cu1 N9 C10 -29.2(13) . . . . ? N12 Cu1 N9 C10 65.4(18) 10_557 . . . ? N12 C9 C30 C35 95.1(8) . . . . ? N12 C9 C30 C31 -85.1(8) . . . . ? N12 C13 C14 N15 -55.5(16) . . . . ? N12 C11 C10 N9 -47.2(19) . . . . ? N15 Cu1 N12 C9 92.6(9) . . . . ? N15 Cu1 N12 C9 80(5) 10_557 . . . ? N15 Cu1 N12 C13 -42(4) 10_557 . . . ? N15 Cu1 N12 C13 -28.8(7) . . . . ? N15 Cu1 N12 C11 -156(6) 10_557 . . . ? N15 Cu1 N12 C11 -142.7(16) . . . . ? N15 Cu1 N15 C14 4.6(16) 10_557 . . . ? N15 Cu1 N15 C16 121.8(7) 10_557 . . . ? N15 Cu1 N17 C2 8.3(14) . . . . ? N15 Cu1 N17 C2 -44(2) 10_557 . . . ? N15 Cu1 N17 C18 66(2) 10_557 . . . ? N15 Cu1 N17 C18 118.1(14) . . . . ? N15 Cu1 N9 C20 165.1(9) . . . . ? N15 Cu1 N9 C20 96.9(15) 10_557 . . . ? N15 Cu1 N9 C19 -148.6(17) 10_557 . . . ? N15 Cu1 N9 C19 -80(2) . . . . ? N15 Cu1 N9 C10 -24.7(14) 10_557 . . . ? N15 Cu1 N9 C10 43.4(19) . . . . ? N17 Cu1 N12 C9 -113.6(10) 10_557 . . . ? N17 Cu1 N12 C9 169.8(14) . . . . ? N17 Cu1 N12 C13 125.0(13) 10_557 . . . ? N17 Cu1 N12 C13 48.3(19) . . . . ? N17 Cu1 N12 C11 -65.5(19) . . . . ? N17 Cu1 N12 C11 11.1(12) 10_557 . . . ? N17 Cu1 N15 C14 -149.1(13) . . . . ? N17 Cu1 N15 C14 -51(2) 10_557 . . . ? N17 Cu1 N15 C16 -31.9(11) . . . . ? N17 Cu1 N15 C16 66.3(16) 10_557 . . . ? N17 Cu1 N17 C2 -139.4(10) 10_557 . . . ? N17 Cu1 N17 C18 -30(2) 10_557 . . . ? N17 Cu1 N9 C20 54(7) 10_557 . . . ? N17 Cu1 N9 C20 -116(2) . . . . ? N17 Cu1 N9 C19 169(10) 10_557 . . . ? N17 Cu1 N9 C19 -1.2(11) . . . . ? N17 Cu1 N9 C10 122.7(17) . . . . ? N17 Cu1 N9 C10 -68(8) 10_557 . . . ? N17 C2 C16 N15 -49(2) . . . . ? N17 C18 C19 N9 -59(2) . . . . ? N9 Cu1 N12 C9 -173.9(13) 10_557 . . . ? N9 Cu1 N12 C9 -120.7(11) . . . . ? N9 Cu1 N12 C13 64.6(17) 10_557 . . . ? N9 Cu1 N12 C13 117.9(12) . . . . ? N9 Cu1 N12 C11 -49.3(19) 10_557 . . . ? N9 Cu1 N12 C11 4.0(12) . . . . ? N9 Cu1 N15 C14 -70.4(18) . . . . ? N9 Cu1 N15 C14 -141.6(13) 10_557 . . . ? N9 Cu1 N15 C16 -24.4(12) 10_557 . . . ? N9 Cu1 N15 C16 46.8(17) . . . . ? N9 Cu1 N17 C2 -129(9) 10_557 . . . ? N9 Cu1 N17 C2 -137.4(19) . . . . ? N9 Cu1 N17 C18 -27.6(8) . . . . ? N9 Cu1 N17 C18 -19(7) 10_557 . . . ? N9 Cu1 N9 C20 -117.3(10) 10_557 . . . ? N9 Cu1 N9 C19 -3(2) 10_557 . . . ? N9 Cu1 N9 C10 121.0(11) 10_557 . . . ? N9 C20 C21 C22 97.9(14) . . . . ? N9 C20 C21 C26 -82.5(13) . . . . ? O39 Cu2 O28 C27 -166.2(7) . . . . ? O39 Cu2 O28 C27 173.3(7) 11_655 . . . ? O39 Cu2 O29 C27 -159.6(8) 11_655 . . 3_586 ? O39 Cu2 O29 C27 -179.9(8) . . . 3_586 ? O39 Cu2 O40 C40 -107(9) . . . 11_655 ? O39 Cu2 O40 C40 58(5) 11_655 . . 11_655 ? O39 Cu2 O40 C40 107(9) 11_655 . . . ? O39 Cu2 O40 C40 -58(5) . . . . ? O39 Cu2 O39 C40 67(2) 11_655 . . . ? O39 Cu2 O39 C40 35.0(12) 11_655 . . 11_655 ? O39 O39 C40 O40 4(7) 11_655 . . . ? O39 O39 C40 C41 -75(2) 11_655 . . . ? C40 O40 C40 C41 -56(2) 11_655 . . . ? C40 O40 C40 O39 -4(6) 11_655 . . 11_655 ? C40 O40 C40 O39 -176(7) 11_655 . . . ? C40 C41 C40 O40 56(2) 11_655 . . . ? C40 C41 C40 O39 85(2) 11_655 . . . ? C40 C41 C40 O39 37.1(14) 11_655 . . 11_655 ? C40 O39 C40 O40 4(7) 11_655 . . . ? C40 O39 C40 C41 -75(2) 11_655 . . . ? C40 O39 C40 O39 0.0 11_655 . . 11_655 ? _database_code_depnum_ccdc_archive 'CCDC 967733'