# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Bu, Xian-He' 'Du, Miao' 'Guo, Ya-Mei' 'Monfort, Monsterrat' 'Ribas, Joan' _publ_contact_author_name 'Prof Xian-He Bu' _publ_contact_author_address ; Chemistry Nankai University 94, Weijin Road Tianjin 300071 CHINA ; _publ_contact_author_email 'BUXH@NANKAI.EDU.CN' _publ_section_title ; Ferromagnetic coupling in a unique Cu(II) metallacyclophane with functionalized diazamesocyclic ligands formed by Cu(II)-directed self-assembly: magneto-structural correlations for dichloro-bridged Cu(II) dinuclear complexes ; data_2 _database_code_CSD 182815 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 Cl4 Cu2 N6 O8' _chemical_formula_weight 779.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.860(4) _cell_length_b 8.114(3) _cell_length_c 32.848(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.908(6) _cell_angle_gamma 90.00 _cell_volume 3160.6(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 1.737 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6238 _exptl_absorpt_correction_T_max 0.7806 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12564 _diffrn_reflns_av_R_equivalents 0.0852 _diffrn_reflns_av_sigmaI/netI 0.1312 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5528 _reflns_number_gt 2463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5528 _refine_ls_number_parameters 379 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1478 _refine_ls_R_factor_gt 0.0611 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1362 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0.106 _refine_ls_shift/su_mean 0.009 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 0.49986(8) 0.62564(14) 0.12501(3) 0.0486(3) Uani 1 1 d . . . Cu2 Cu 0.23827(8) 0.75349(13) 0.14906(3) 0.0442(3) Uani 1 1 d . . . Cl1 Cl 0.33528(17) 0.5282(3) 0.17172(6) 0.0520(6) Uani 1 1 d . . . Cl2 Cl 0.41709(19) 0.8724(3) 0.11123(7) 0.0601(7) Uani 1 1 d . . . N1 N 0.6038(6) 0.4295(10) 0.1309(2) 0.054(2) Uani 1 1 d . . . N2 N 0.6043(6) 0.7077(10) 0.1685(2) 0.063(2) Uani 1 1 d . . . H2C H 0.5727 0.7954 0.1813 0.076 Uiso 1 1 calc R . . N3 N 0.4476(6) 0.5029(10) 0.0756(2) 0.0494(18) Uani 1 1 d . . . N4 N 0.2569(7) 0.8909(9) 0.1987(2) 0.061(2) Uani 1 1 d . . . H4C H 0.3208 0.8619 0.2126 0.073 Uiso 1 1 calc R . . N5 N 0.1313(6) 0.9412(8) 0.13618(19) 0.0466(18) Uani 1 1 d . . . N6 N 0.1521(6) 0.6440(9) 0.10369(19) 0.0450(18) Uani 1 1 d . . . C1 C 0.7089(9) 0.7602(18) 0.1483(3) 0.095(4) Uani 1 1 d . . . H1A H 0.6904 0.8383 0.1269 0.114 Uiso 1 1 calc R . . H1B H 0.7580 0.8151 0.1679 0.114 Uiso 1 1 calc R . . C2 C 0.7689(11) 0.617(2) 0.1306(4) 0.119(5) Uani 1 1 d . . . H2A H 0.8226 0.6606 0.1115 0.143 Uiso 1 1 calc R . . H2B H 0.8127 0.5670 0.1526 0.143 Uiso 1 1 calc R . . C3 C 0.7096(9) 0.4850(16) 0.1102(3) 0.079(3) Uani 1 1 d . . . H3A H 0.7600 0.3914 0.1080 0.095 Uiso 1 1 calc R . . H3B H 0.6901 0.5207 0.0828 0.095 Uiso 1 1 calc R . . C4 C 0.6232(8) 0.5715(15) 0.1982(3) 0.075(3) Uani 1 1 d . . . H4A H 0.5641 0.5724 0.2183 0.091 Uiso 1 1 calc R . . H4B H 0.6949 0.5871 0.2123 0.091 Uiso 1 1 calc R . . C5 C 0.6230(8) 0.4038(13) 0.1755(3) 0.070(3) Uani 1 1 d . . . H5A H 0.6947 0.3488 0.1801 0.084 Uiso 1 1 calc R . . H5B H 0.5640 0.3339 0.1862 0.084 Uiso 1 1 calc R . . C6 C 0.5503(8) 0.2891(13) 0.1108(3) 0.069(3) Uani 1 1 d . . . H6A H 0.5023 0.2320 0.1299 0.083 Uiso 1 1 calc R . . H6B H 0.6076 0.2126 0.1018 0.083 Uiso 1 1 calc R . . C7 C 0.4805(7) 0.3471(13) 0.0746(3) 0.055(2) Uani 1 1 d . . . C8 C 0.4468(9) 0.2419(14) 0.0433(3) 0.076(3) Uani 1 1 d . . . H8A H 0.4696 0.1322 0.0432 0.091 Uiso 1 1 calc R . . C9 C 0.3797(10) 0.3025(17) 0.0127(3) 0.082(4) Uani 1 1 d . . . H9A H 0.3557 0.2339 -0.0084 0.099 Uiso 1 1 calc R . . C10 C 0.3475(8) 0.4647(16) 0.0132(3) 0.072(3) Uani 1 1 d . . . H10A H 0.3014 0.5072 -0.0074 0.087 Uiso 1 1 calc R . . C11 C 0.3841(7) 0.5618(14) 0.0441(3) 0.063(3) Uani 1 1 d . . . H11A H 0.3650 0.6730 0.0439 0.076 Uiso 1 1 calc R . . C12 C 0.1559(10) 0.8557(14) 0.2235(3) 0.078(3) Uani 1 1 d . . . H12A H 0.1690 0.8946 0.2511 0.094 Uiso 1 1 calc R . . H12B H 0.1440 0.7375 0.2246 0.094 Uiso 1 1 calc R . . C13 C 0.0497(9) 0.9390(13) 0.2057(3) 0.073(3) Uani 1 1 d . . . H13A H -0.0152 0.8991 0.2204 0.088 Uiso 1 1 calc R . . H13B H 0.0553 1.0567 0.2105 0.088 Uiso 1 1 calc R . . C14 C 0.0289(8) 0.9108(12) 0.1606(3) 0.062(3) Uani 1 1 d . . . H14A H 0.0041 0.7981 0.1564 0.075 Uiso 1 1 calc R . . H14B H -0.0310 0.9833 0.1512 0.075 Uiso 1 1 calc R . . C15 C 0.2625(9) 1.0679(12) 0.1859(3) 0.076(3) Uani 1 1 d . . . H15A H 0.2355 1.1379 0.2076 0.091 Uiso 1 1 calc R . . H15B H 0.3400 1.0979 0.1805 0.091 Uiso 1 1 calc R . . C16 C 0.1901(8) 1.0932(11) 0.1477(3) 0.058(3) Uani 1 1 d . . . H16A H 0.1353 1.1795 0.1525 0.069 Uiso 1 1 calc R . . H16B H 0.2375 1.1282 0.1255 0.069 Uiso 1 1 calc R . . C17 C 0.1033(8) 0.9255(10) 0.0919(3) 0.056(3) Uani 1 1 d . . . H17A H 0.1644 0.9691 0.0759 0.067 Uiso 1 1 calc R . . H17B H 0.0354 0.9873 0.0854 0.067 Uiso 1 1 calc R . . C18 C 0.0859(7) 0.7479(12) 0.0826(2) 0.047(2) Uani 1 1 d . . . C19 C 0.0062(8) 0.6886(15) 0.0548(3) 0.063(3) Uani 1 1 d . . . H19A H -0.0393 0.7616 0.0402 0.076 Uiso 1 1 calc R . . C20 C -0.0047(9) 0.5261(16) 0.0493(3) 0.072(3) Uani 1 1 d . . . H20A H -0.0597 0.4855 0.0315 0.086 Uiso 1 1 calc R . . C21 C 0.0644(10) 0.4202(14) 0.0698(3) 0.080(3) Uani 1 1 d . . . H21A H 0.0591 0.3071 0.0655 0.096 Uiso 1 1 calc R . . C22 C 0.1433(8) 0.4847(13) 0.0972(3) 0.065(3) Uani 1 1 d . . . H22A H 0.1911 0.4131 0.1113 0.079 Uiso 1 1 calc R . . Cl3 Cl 0.7925(2) 0.0763(4) 0.03356(10) 0.0705(8) Uani 1 1 d . . . O1 O 0.8608(14) 0.147(3) 0.0569(9) 0.401(17) Uani 1 1 d . . . O2 O 0.721(2) 0.176(3) 0.0220(6) 0.386(15) Uani 1 1 d . . . O3 O 0.8472(12) -0.0150(17) 0.0050(4) 0.212(6) Uani 1 1 d . . . O4 O 0.7423(18) -0.0243(18) 0.0574(4) 0.276(10) Uani 1 1 d . . . Cl4 Cl 0.9659(3) 0.4415(4) 0.23103(11) 0.0997(11) Uani 1 1 d D . . O5 O 0.8821(8) 0.3242(11) 0.2217(4) 0.210(7) Uani 1 1 d D . . O6 O 0.9355(13) 0.6000(11) 0.2174(5) 0.324(13) Uani 1 1 d D . . O7 O 1.0725(8) 0.398(2) 0.2145(7) 0.42(2) Uani 1 1 d D . . O8 O 0.9837(14) 0.449(2) 0.2747(3) 0.48(2) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0422(6) 0.0583(7) 0.0451(6) 0.0064(6) -0.0051(5) -0.0022(6) Cu2 0.0452(6) 0.0426(6) 0.0444(6) 0.0034(5) -0.0088(5) 0.0006(5) Cl1 0.0477(13) 0.0555(14) 0.0528(13) 0.0218(12) 0.0007(10) 0.0075(12) Cl2 0.0580(15) 0.0528(14) 0.0695(15) 0.0167(13) 0.0021(12) -0.0038(13) N1 0.043(4) 0.071(6) 0.048(4) 0.011(4) 0.002(4) 0.014(4) N2 0.049(5) 0.081(6) 0.059(5) -0.003(5) -0.002(4) -0.005(4) N3 0.044(4) 0.063(5) 0.041(4) -0.001(4) -0.002(3) -0.004(4) N4 0.068(5) 0.060(6) 0.054(5) -0.004(4) -0.024(4) -0.003(5) N5 0.054(5) 0.045(4) 0.040(4) 0.004(4) -0.005(4) -0.004(4) N6 0.051(4) 0.040(5) 0.043(4) 0.005(4) -0.004(3) -0.003(4) C1 0.072(8) 0.131(12) 0.082(8) 0.013(8) -0.004(7) -0.048(9) C2 0.071(9) 0.170(16) 0.118(11) -0.010(11) 0.038(8) -0.020(11) C3 0.059(7) 0.110(10) 0.068(7) -0.001(7) 0.012(6) 0.005(7) C4 0.051(6) 0.128(11) 0.046(6) 0.011(7) -0.009(5) 0.012(7) C5 0.059(6) 0.090(9) 0.059(6) 0.014(6) -0.003(5) 0.018(6) C6 0.061(6) 0.064(7) 0.082(7) 0.003(6) -0.002(6) -0.002(6) C7 0.046(6) 0.063(7) 0.056(6) 0.004(6) 0.003(5) -0.007(5) C8 0.092(8) 0.069(7) 0.067(7) -0.014(7) 0.010(6) -0.011(7) C9 0.086(8) 0.098(10) 0.063(7) -0.021(7) -0.012(6) -0.039(8) C10 0.058(7) 0.110(10) 0.048(6) -0.007(7) -0.011(5) -0.011(7) C11 0.049(6) 0.092(8) 0.048(6) 0.002(6) -0.008(5) 0.003(6) C12 0.115(10) 0.080(8) 0.041(6) -0.009(6) -0.001(6) -0.005(8) C13 0.089(8) 0.067(7) 0.064(7) -0.001(6) 0.024(6) 0.003(6) C14 0.058(6) 0.070(7) 0.059(6) -0.003(5) 0.009(5) 0.003(5) C15 0.080(8) 0.063(7) 0.083(8) -0.015(6) -0.007(6) -0.017(6) C16 0.067(6) 0.044(6) 0.062(6) 0.001(5) -0.004(5) 0.002(5) C17 0.068(6) 0.046(6) 0.053(6) 0.010(5) -0.012(5) 0.011(5) C18 0.049(5) 0.061(6) 0.029(4) 0.014(5) 0.004(4) 0.007(5) C19 0.061(7) 0.085(8) 0.044(6) -0.005(6) -0.009(5) -0.001(6) C20 0.077(8) 0.095(9) 0.042(6) -0.005(7) -0.008(5) -0.032(8) C21 0.103(9) 0.068(8) 0.069(7) -0.012(6) -0.006(7) -0.030(7) C22 0.069(7) 0.048(6) 0.079(7) 0.007(6) -0.011(6) -0.009(6) Cl3 0.0517(16) 0.0659(18) 0.094(2) -0.0007(17) -0.0054(15) 0.0048(14) O1 0.178(14) 0.33(3) 0.69(4) -0.33(3) -0.06(2) -0.039(16) O2 0.37(3) 0.44(3) 0.35(2) 0.15(2) 0.00(2) 0.30(3) O3 0.259(14) 0.208(13) 0.174(10) 0.029(10) 0.115(10) 0.118(12) O4 0.49(3) 0.163(13) 0.179(12) 0.010(10) 0.198(16) -0.081(16) Cl4 0.077(2) 0.087(2) 0.134(3) 0.046(2) -0.045(2) -0.0081(19) O5 0.129(8) 0.169(11) 0.329(16) 0.110(11) -0.136(10) -0.066(8) O6 0.285(19) 0.195(15) 0.48(3) 0.155(17) -0.26(2) -0.101(14) O7 0.137(14) 0.40(3) 0.74(5) -0.38(3) 0.02(2) -0.062(16) O8 0.36(3) 0.68(5) 0.40(3) 0.34(3) -0.30(2) -0.32(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.991(7) . ? Cu1 N3 1.996(7) . ? Cu1 N1 2.020(7) . ? Cu1 Cl2 2.273(3) . ? Cu1 Cl1 2.624(2) . ? Cu2 N4 1.986(7) . ? Cu2 N6 2.001(6) . ? Cu2 N5 2.022(7) . ? Cu2 Cl1 2.279(2) . ? Cu2 Cl2 2.656(3) . ? N1 C6 1.457(11) . ? N1 C3 1.506(12) . ? N1 C5 1.495(10) . ? N2 C1 1.479(12) . ? N2 C4 1.487(11) . ? N3 C7 1.324(12) . ? N3 C11 1.355(10) . ? N4 C12 1.486(12) . ? N4 C15 1.498(11) . ? N5 C16 1.463(10) . ? N5 C14 1.487(10) . ? N5 C17 1.491(10) . ? N6 C22 1.315(11) . ? N6 C18 1.338(10) . ? C1 C2 1.487(17) . ? C2 C3 1.440(16) . ? C4 C5 1.551(13) . ? C6 C7 1.514(12) . ? C7 C8 1.389(12) . ? C8 C9 1.363(14) . ? C9 C10 1.370(15) . ? C10 C11 1.352(12) . ? C12 C13 1.536(13) . ? C13 C14 1.515(12) . ? C15 C16 1.525(12) . ? C17 C18 1.488(12) . ? C18 C19 1.388(11) . ? C19 C20 1.338(14) . ? C20 C21 1.358(14) . ? C21 C22 1.390(12) . ? Cl3 O2 1.226(13) . ? Cl3 O1 1.246(16) . ? Cl3 O4 1.283(12) . ? Cl3 O3 1.366(11) . ? Cl4 O5 1.407(6) . ? Cl4 O6 1.407(8) . ? Cl4 O7 1.430(8) . ? Cl4 O8 1.449(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N3 158.9(3) . . ? N2 Cu1 N1 79.8(3) . . ? N3 Cu1 N1 82.3(3) . . ? N2 Cu1 Cl2 96.3(3) . . ? N3 Cu1 Cl2 98.6(2) . . ? N1 Cu1 Cl2 166.9(2) . . ? N2 Cu1 Cl1 98.1(2) . . ? N3 Cu1 Cl1 95.8(2) . . ? N1 Cu1 Cl1 99.5(2) . . ? Cl2 Cu1 Cl1 93.39(8) . . ? N4 Cu2 N6 155.5(3) . . ? N4 Cu2 N5 79.1(3) . . ? N6 Cu2 N5 82.4(3) . . ? N4 Cu2 Cl1 97.6(2) . . ? N6 Cu2 Cl1 97.8(2) . . ? N5 Cu2 Cl1 169.8(2) . . ? N4 Cu2 Cl2 95.8(2) . . ? N6 Cu2 Cl2 102.4(2) . . ? N5 Cu2 Cl2 97.5(2) . . ? Cl1 Cu2 Cl2 92.39(8) . . ? Cu2 Cl1 Cu1 86.76(8) . . ? Cu1 Cl2 Cu2 86.11(8) . . ? C6 N1 C3 112.9(8) . . ? C6 N1 C5 113.2(8) . . ? C3 N1 C5 111.7(7) . . ? C6 N1 Cu1 108.2(5) . . ? C3 N1 Cu1 103.5(6) . . ? C5 N1 Cu1 106.7(6) . . ? C1 N2 C4 112.9(8) . . ? C1 N2 Cu1 106.9(6) . . ? C4 N2 Cu1 107.9(6) . . ? C7 N3 C11 118.6(8) . . ? C7 N3 Cu1 114.2(6) . . ? C11 N3 Cu1 127.3(7) . . ? C12 N4 C15 112.2(8) . . ? C12 N4 Cu2 105.2(6) . . ? C15 N4 Cu2 108.2(5) . . ? C16 N5 C14 113.0(7) . . ? C16 N5 C17 114.9(7) . . ? C14 N5 C17 109.9(7) . . ? C16 N5 Cu2 106.6(5) . . ? C14 N5 Cu2 106.1(5) . . ? C17 N5 Cu2 105.6(5) . . ? C22 N6 C18 119.4(8) . . ? C22 N6 Cu2 126.6(6) . . ? C18 N6 Cu2 113.3(6) . . ? C2 C1 N2 111.1(10) . . ? C3 C2 C1 122.0(11) . . ? C2 C3 N1 114.6(9) . . ? N2 C4 C5 109.8(7) . . ? N1 C5 C4 110.3(8) . . ? N1 C6 C7 110.0(8) . . ? N3 C7 C8 121.6(9) . . ? N3 C7 C6 115.8(9) . . ? C8 C7 C6 122.5(10) . . ? C9 C8 C7 118.7(11) . . ? C8 C9 C10 119.8(10) . . ? C11 C10 C9 118.9(10) . . ? C10 C11 N3 122.3(10) . . ? N4 C12 C13 111.7(8) . . ? C14 C13 C12 115.1(8) . . ? N5 C14 C13 112.4(7) . . ? C16 C15 N4 109.5(7) . . ? N5 C16 C15 111.0(7) . . ? N5 C17 C18 108.2(7) . . ? N6 C18 C19 120.7(9) . . ? N6 C18 C17 115.1(7) . . ? C19 C18 C17 124.2(9) . . ? C20 C19 C18 119.6(10) . . ? C19 C20 C21 120.0(10) . . ? C20 C21 C22 118.5(10) . . ? N6 C22 C21 121.8(10) . . ? O2 Cl3 O1 108.8(16) . . ? O2 Cl3 O4 106.6(15) . . ? O1 Cl3 O4 102.9(16) . . ? O2 Cl3 O3 118.5(12) . . ? O1 Cl3 O3 111.1(11) . . ? O4 Cl3 O3 107.7(9) . . ? O5 Cl4 O6 111.9(5) . . ? O5 Cl4 O7 112.1(7) . . ? O6 Cl4 O7 109.2(8) . . ? O5 Cl4 O8 109.7(6) . . ? O6 Cl4 O8 108.0(8) . . ? O7 Cl4 O8 105.8(7) . . ? 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 N4 Cu2 Cl1 Cu1 -104.3(2) . . . . ? N6 Cu2 Cl1 Cu1 94.8(2) . . . . ? N5 Cu2 Cl1 Cu1 -174.7(11) . . . . ? Cl2 Cu2 Cl1 Cu1 -8.13(8) . . . . ? N2 Cu1 Cl1 Cu2 106.4(3) . . . . ? N3 Cu1 Cl1 Cu2 -89.5(2) . . . . ? N1 Cu1 Cl1 Cu2 -172.6(2) . . . . ? Cl2 Cu1 Cl1 Cu2 9.53(9) . . . . ? N2 Cu1 Cl2 Cu2 -106.7(2) . . . . ? N3 Cu1 Cl2 Cu2 88.2(2) . . . . ? N1 Cu1 Cl2 Cu2 -179(44) . . . . ? Cl1 Cu1 Cl2 Cu2 -8.17(8) . . . . ? N4 Cu2 Cl2 Cu1 107.3(2) . . . . ? N6 Cu2 Cl2 Cu1 -89.2(2) . . . . ? N5 Cu2 Cl2 Cu1 -172.97(19) . . . . ? Cl1 Cu2 Cl2 Cu1 9.41(9) . . . . ? N2 Cu1 N1 C6 165.0(6) . . . . ? N3 Cu1 N1 C6 -26.3(6) . . . . ? Cl2 Cu1 N1 C6 -121.1(10) . . . . ? Cl1 Cu1 N1 C6 68.4(6) . . . . ? N2 Cu1 N1 C3 -75.0(6) . . . . ? N3 Cu1 N1 C3 93.8(6) . . . . ? Cl2 Cu1 N1 C3 -1.1(14) . . . . ? Cl1 Cu1 N1 C3 -171.6(5) . . . . ? N2 Cu1 N1 C5 42.9(6) . . . . ? N3 Cu1 N1 C5 -148.3(6) . . . . ? Cl2 Cu1 N1 C5 116.8(10) . . . . ? Cl1 Cu1 N1 C5 -53.7(6) . . . . ? N3 Cu1 N2 C1 45.7(13) . . . . ? N1 Cu1 N2 C1 78.1(8) . . . . ? Cl2 Cu1 N2 C1 -89.2(7) . . . . ? Cl1 Cu1 N2 C1 176.4(7) . . . . ? N3 Cu1 N2 C4 -76.0(11) . . . . ? N1 Cu1 N2 C4 -43.6(6) . . . . ? Cl2 Cu1 N2 C4 149.1(6) . . . . ? Cl1 Cu1 N2 C4 54.7(6) . . . . ? N2 Cu1 N3 C7 46.9(12) . . . . ? N1 Cu1 N3 C7 14.7(6) . . . . ? Cl2 Cu1 N3 C7 -178.5(6) . . . . ? Cl1 Cu1 N3 C7 -84.1(6) . . . . ? N2 Cu1 N3 C11 -133.1(9) . . . . ? N1 Cu1 N3 C11 -165.3(7) . . . . ? Cl2 Cu1 N3 C11 1.5(7) . . . . ? Cl1 Cu1 N3 C11 95.8(7) . . . . ? N6 Cu2 N4 C12 36.4(11) . . . . ? N5 Cu2 N4 C12 77.9(6) . . . . ? Cl1 Cu2 N4 C12 -92.3(6) . . . . ? Cl2 Cu2 N4 C12 174.4(6) . . . . ? N6 Cu2 N4 C15 -83.7(10) . . . . ? N5 Cu2 N4 C15 -42.2(6) . . . . ? Cl1 Cu2 N4 C15 147.6(6) . . . . ? Cl2 Cu2 N4 C15 54.4(6) . . . . ? N4 Cu2 N5 C16 43.9(6) . . . . ? N6 Cu2 N5 C16 -152.1(6) . . . . ? Cl1 Cu2 N5 C16 115.9(11) . . . . ? Cl2 Cu2 N5 C16 -50.5(5) . . . . ? N4 Cu2 N5 C14 -76.7(5) . . . . ? N6 Cu2 N5 C14 87.2(5) . . . . ? Cl1 Cu2 N5 C14 -4.7(15) . . . . ? Cl2 Cu2 N5 C14 -171.2(5) . . . . ? N4 Cu2 N5 C17 166.6(6) . . . . ? N6 Cu2 N5 C17 -29.5(5) . . . . ? Cl1 Cu2 N5 C17 -121.4(11) . . . . ? Cl2 Cu2 N5 C17 72.1(5) . . . . ? N4 Cu2 N6 C22 -117.0(9) . . . . ? N5 Cu2 N6 C22 -158.0(8) . . . . ? Cl1 Cu2 N6 C22 11.7(8) . . . . ? Cl2 Cu2 N6 C22 105.9(8) . . . . ? N4 Cu2 N6 C18 52.8(10) . . . . ? N5 Cu2 N6 C18 11.9(6) . . . . ? Cl1 Cu2 N6 C18 -178.5(5) . . . . ? Cl2 Cu2 N6 C18 -84.2(6) . . . . ? C4 N2 C1 C2 51.5(12) . . . . ? Cu1 N2 C1 C2 -66.9(11) . . . . ? N2 C1 C2 C3 40.5(17) . . . . ? C1 C2 C3 N1 -42.4(17) . . . . ? C6 N1 C3 C2 -176.2(10) . . . . ? C5 N1 C3 C2 -47.3(13) . . . . ? Cu1 N1 C3 C2 67.1(11) . . . . ? C1 N2 C4 C5 -83.4(10) . . . . ? Cu1 N2 C4 C5 34.5(9) . . . . ? C6 N1 C5 C4 -152.4(8) . . . . ? C3 N1 C5 C4 78.9(10) . . . . ? Cu1 N1 C5 C4 -33.5(9) . . . . ? N2 C4 C5 N1 -0.1(11) . . . . ? C3 N1 C6 C7 -81.3(10) . . . . ? C5 N1 C6 C7 150.7(8) . . . . ? Cu1 N1 C6 C7 32.6(9) . . . . ? C11 N3 C7 C8 -3.2(13) . . . . ? Cu1 N3 C7 C8 176.8(7) . . . . ? C11 N3 C7 C6 -179.5(8) . . . . ? Cu1 N3 C7 C6 0.5(10) . . . . ? N1 C6 C7 N3 -22.7(11) . . . . ? N1 C6 C7 C8 161.1(9) . . . . ? N3 C7 C8 C9 1.0(15) . . . . ? C6 C7 C8 C9 177.0(9) . . . . ? C7 C8 C9 C10 0.5(16) . . . . ? C8 C9 C10 C11 0.4(17) . . . . ? C9 C10 C11 N3 -2.8(15) . . . . ? C7 N3 C11 C10 4.2(13) . . . . ? Cu1 N3 C11 C10 -175.8(7) . . . . ? C15 N4 C12 C13 43.1(10) . . . . ? Cu2 N4 C12 C13 -74.3(9) . . . . ? N4 C12 C13 C14 49.8(12) . . . . ? C16 N5 C14 C13 -45.4(10) . . . . ? C17 N5 C14 C13 -175.2(7) . . . . ? Cu2 N5 C14 C13 71.1(8) . . . . ? C12 C13 C14 N5 -48.4(12) . . . . ? C12 N4 C15 C16 -83.6(9) . . . . ? Cu2 N4 C15 C16 32.0(10) . . . . ? C14 N5 C16 C15 79.7(9) . . . . ? C17 N5 C16 C15 -153.0(8) . . . . ? Cu2 N5 C16 C15 -36.4(9) . . . . ? N4 C15 C16 N5 3.5(11) . . . . ? C16 N5 C17 C18 158.7(7) . . . . ? C14 N5 C17 C18 -72.6(9) . . . . ? Cu2 N5 C17 C18 41.5(8) . . . . ? C22 N6 C18 C19 1.9(13) . . . . ? Cu2 N6 C18 C19 -168.8(6) . . . . ? C22 N6 C18 C17 -179.4(8) . . . . ? Cu2 N6 C18 C17 9.9(9) . . . . ? N5 C17 C18 N6 -35.1(10) . . . . ? N5 C17 C18 C19 143.6(8) . . . . ? N6 C18 C19 C20 0.3(14) . . . . ? C17 C18 C19 C20 -178.3(9) . . . . ? C18 C19 C20 C21 -2.2(16) . . . . ? C19 C20 C21 C22 2.0(16) . . . . ? C18 N6 C22 C21 -2.1(14) . . . . ? Cu2 N6 C22 C21 167.2(7) . . . . ? C20 C21 C22 N6 0.2(16) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.846 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.100 data_1 _database_code_CSD 182816 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H50 Cl6 Cu2 N8 O8' _chemical_formula_weight 1062.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.916(3) _cell_length_b 19.774(5) _cell_length_c 13.027(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.411(6) _cell_angle_gamma 90.00 _cell_volume 2203.1(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 1.388 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6809 _exptl_absorpt_correction_T_max 0.8188 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8980 _diffrn_reflns_av_R_equivalents 0.0819 _diffrn_reflns_av_sigmaI/netI 0.1413 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3850 _reflns_number_gt 1456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0928P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3850 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.1684 _refine_ls_wR_factor_gt 0.1285 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 1.01822(11) 0.08125(5) 0.58443(8) 0.0687(4) Uani 1 1 d . . . Cl1 Cl 0.9445(3) 0.11493(11) 0.72927(17) 0.0822(7) Uani 1 1 d . . . Cl2 Cl 1.1123(2) 0.05507(10) 0.44271(16) 0.0702(6) Uani 1 1 d . . . N1 N 0.8153(7) 0.1168(3) 0.4863(5) 0.0607(17) Uani 1 1 d . . . N2 N 0.3011(7) 0.1721(3) 0.2050(5) 0.0697(19) Uani 1 1 d . . . N3 N 0.2614(10) 0.0548(4) 0.1065(8) 0.106(3) Uani 1 1 d . . . N4 N 1.2278(7) 0.0568(3) 0.6809(5) 0.0630(18) Uani 1 1 d . . . C1 C 0.8154(9) 0.1623(4) 0.4091(6) 0.063(2) Uani 1 1 d . . . H1A H 0.9099 0.1740 0.3969 0.075 Uiso 1 1 calc R . . C2 C 0.6777(12) 0.1923(4) 0.3468(6) 0.079(3) Uani 1 1 d . . . H2A H 0.6808 0.2241 0.2948 0.095 Uiso 1 1 calc R . . C3 C 0.5368(10) 0.1741(4) 0.3638(7) 0.073(3) Uani 1 1 d . . . C4 C 0.5393(10) 0.1267(5) 0.4431(7) 0.078(3) Uani 1 1 d . . . H4A H 0.4465 0.1137 0.4567 0.094 Uiso 1 1 calc R . . C5 C 0.6754(10) 0.0998(4) 0.5000(7) 0.074(2) Uani 1 1 d . . . H5A H 0.6734 0.0676 0.5517 0.089 Uiso 1 1 calc R . . C6 C 0.3881(11) 0.2099(4) 0.3008(8) 0.115(4) Uani 1 1 d . . . H6A H 0.3209 0.2166 0.3470 0.138 Uiso 1 1 calc R . . H6B H 0.4152 0.2541 0.2791 0.138 Uiso 1 1 calc R . . C7 C 0.322(2) 0.1995(5) 0.1134(10) 0.196(8) Uani 1 1 d . . . H7A H 0.4330 0.2063 0.1247 0.235 Uiso 1 1 calc R . . H7B H 0.2731 0.2438 0.1037 0.235 Uiso 1 1 calc R . . C8 C 0.2603(17) 0.1609(5) 0.0106(8) 0.142(5) Uani 1 1 d . . . H8A H 0.1515 0.1734 -0.0196 0.171 Uiso 1 1 calc R . . H8B H 0.3162 0.1766 -0.0388 0.171 Uiso 1 1 calc R . . C9 C 0.2685(17) 0.0876(6) 0.0129(11) 0.139(5) Uani 1 1 d . . . H9A H 0.1836 0.0706 -0.0456 0.167 Uiso 1 1 calc R . . H9B H 0.3654 0.0745 -0.0015 0.167 Uiso 1 1 calc R . . C10 C 0.088(2) 0.0611(9) 0.1044(17) 0.216(9) Uani 1 1 d . . . H10A H 0.0273 0.0697 0.0311 0.260 Uiso 1 1 calc R . . H10B H 0.0543 0.0177 0.1248 0.260 Uiso 1 1 calc R . . C11 C 0.0484(14) 0.1117(9) 0.1705(13) 0.151(5) Uani 1 1 d . . . H11A H 0.0623 0.0916 0.2404 0.182 Uiso 1 1 calc R . . H11B H -0.0625 0.1207 0.1414 0.182 Uiso 1 1 calc R . . C12 C 0.1271(15) 0.1769(9) 0.1877(12) 0.193(8) Uani 1 1 d . . . H12A H 0.1074 0.1984 0.2496 0.231 Uiso 1 1 calc R . . H12B H 0.0827 0.2055 0.1261 0.231 Uiso 1 1 calc R . . C13 C 0.3093(15) -0.0145(6) 0.1171(11) 0.206(8) Uani 1 1 d . . . H13A H 0.2969 -0.0329 0.0461 0.247 Uiso 1 1 calc R . . H13B H 0.2399 -0.0393 0.1488 0.247 Uiso 1 1 calc R . . C14 C 1.2576(9) -0.0022(4) 0.7248(7) 0.072(2) Uani 1 1 d . . . H14A H 1.1774 -0.0339 0.7114 0.086 Uiso 1 1 calc R . . C15 C 1.4019(11) -0.0203(4) 0.7902(8) 0.101(4) Uani 1 1 d . . . H15A H 1.4184 -0.0640 0.8175 0.121 Uiso 1 1 calc R . . C16 C 1.5228(10) 0.0264(5) 0.8157(8) 0.108(4) Uani 1 1 d . . . C17 C 1.4907(11) 0.0882(5) 0.7689(10) 0.125(5) Uani 1 1 d . . . H17A H 1.5681 0.1211 0.7802 0.150 Uiso 1 1 calc R . . C18 C 1.3448(11) 0.1010(4) 0.7058(8) 0.092(3) Uani 1 1 d . . . H18A H 1.3246 0.1444 0.6774 0.110 Uiso 1 1 calc R . . Cl3 Cl 0.1925(4) 0.27680(18) 0.5216(3) 0.1150(10) Uani 1 1 d . . . O1 O 0.3368(12) 0.2507(6) 0.5399(10) 0.216(5) Uani 1 1 d . . . O2 O 0.1241(12) 0.2263(4) 0.5769(8) 0.163(3) Uani 1 1 d . . . O3 O 0.0928(11) 0.2678(4) 0.4122(8) 0.162(3) Uani 1 1 d . . . O4 O 0.1768(13) 0.3404(5) 0.5592(9) 0.199(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 Cu1 0.0522(6) 0.0837(7) 0.0619(7) 0.0028(5) 0.0024(5) 0.0166(5) Cl1 0.0813(15) 0.0902(15) 0.0729(15) 0.0017(12) 0.0182(12) 0.0181(13) Cl2 0.0586(12) 0.0747(13) 0.0727(14) -0.0020(11) 0.0111(10) 0.0035(10) N1 0.044(4) 0.070(4) 0.065(5) 0.002(4) 0.010(3) 0.010(3) N2 0.048(4) 0.081(5) 0.062(4) -0.002(4) -0.014(3) 0.010(3) N3 0.080(6) 0.071(6) 0.119(7) 0.000(5) -0.051(5) 0.027(4) N4 0.060(4) 0.056(4) 0.061(4) -0.001(3) -0.003(3) 0.008(4) C1 0.061(5) 0.065(5) 0.057(5) 0.000(4) 0.009(4) -0.014(4) C2 0.102(8) 0.065(6) 0.055(6) 0.004(4) -0.003(5) -0.011(6) C3 0.055(6) 0.053(5) 0.092(7) -0.015(5) -0.011(5) 0.015(4) C4 0.049(5) 0.095(7) 0.082(6) 0.012(6) 0.007(5) 0.011(5) C5 0.064(6) 0.081(6) 0.075(6) 0.017(5) 0.015(5) 0.011(5) C6 0.093(7) 0.080(6) 0.126(9) -0.022(6) -0.043(7) 0.032(6) C7 0.45(3) 0.071(7) 0.114(10) -0.005(7) 0.153(14) -0.040(11) C8 0.274(16) 0.066(7) 0.081(8) 0.008(6) 0.040(9) -0.006(8) C9 0.194(14) 0.108(10) 0.134(12) -0.055(9) 0.077(10) -0.041(9) C10 0.160(17) 0.179(16) 0.34(3) -0.102(17) 0.122(16) -0.082(12) C11 0.074(8) 0.201(15) 0.173(14) 0.039(12) 0.023(9) -0.009(10) C12 0.099(10) 0.30(2) 0.197(15) -0.143(14) 0.063(10) -0.084(12) C13 0.165(11) 0.078(8) 0.257(16) -0.019(9) -0.134(11) 0.021(8) C14 0.058(5) 0.061(6) 0.082(6) -0.004(5) -0.005(5) -0.004(5) C15 0.108(8) 0.038(5) 0.117(8) 0.004(5) -0.032(6) 0.008(5) C16 0.086(7) 0.049(5) 0.130(8) -0.014(5) -0.066(6) 0.020(5) C17 0.064(6) 0.062(6) 0.203(12) -0.003(7) -0.036(7) -0.008(5) C18 0.072(7) 0.063(6) 0.123(8) 0.036(5) 0.000(6) 0.005(5) Cl3 0.108(3) 0.108(3) 0.132(3) -0.025(2) 0.039(2) -0.002(2) O1 0.119(8) 0.195(10) 0.299(14) -0.044(9) 0.003(8) -0.012(7) O2 0.192(9) 0.106(6) 0.176(9) 0.010(6) 0.024(7) -0.002(6) O3 0.161(8) 0.155(7) 0.157(8) 0.019(6) 0.026(7) -0.030(6) O4 0.236(11) 0.130(7) 0.237(11) -0.052(8) 0.077(9) -0.029(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 Cu1 N4 1.995(6) . ? Cu1 N1 2.023(6) . ? Cu1 Cl1 2.266(3) . ? Cu1 Cl2 2.292(2) . ? Cu1 Cl2 2.918(3) . 3_756 N1 C1 1.350(9) . ? N1 C5 1.352(9) . ? N2 C7 1.369(11) . ? N2 C6 1.473(10) . ? N2 C12 1.507(13) . ? N3 C9 1.398(13) . ? N3 C13 1.429(12) . ? N3 C10 1.545(17) . ? N4 C14 1.292(9) . ? N4 C18 1.329(10) . ? C1 C2 1.399(10) . ? C2 C3 1.383(11) . ? C3 C4 1.390(11) . ? C3 C6 1.523(10) . ? C4 C5 1.341(10) . ? C7 C8 1.504(14) . ? C8 C9 1.451(14) . ? C10 C11 1.427(17) . ? C11 C12 1.455(18) . ? C13 C16 1.524(12) 3_756 ? C14 C15 1.375(10) . ? C15 C16 1.386(11) . ? C16 C17 1.359(12) . ? C16 C13 1.524(12) 3_756 ? C17 C18 1.353(11) . ? Cl3 O1 1.344(11) . ? Cl3 O4 1.371(9) . ? Cl3 O2 1.461(10) . ? Cl3 O3 1.462(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 N1 173.5(3) . . ? N4 Cu1 Cl1 89.2(2) . . ? N1 Cu1 Cl1 90.4(2) . . ? N4 Cu1 Cl2 87.8(2) . . ? N1 Cu1 Cl2 92.0(2) . . ? Cl1 Cu1 Cl2 174.27(9) . . ? Cl1 Cu1 Cl2 100.0(4) . . 3756 Cl2 Cu1 Cl2 85.3(2) . . 3756 N1 Cu1 Cl2 89.4(2) . . 3756 N4 Cu1 Cl2 97.1(2) . . 3756 C1 N1 C5 117.3(7) . . ? C1 N1 Cu1 120.9(5) . . ? C5 N1 Cu1 121.6(6) . . ? C7 N2 C6 111.7(9) . . ? C7 N2 C12 103.3(11) . . ? C6 N2 C12 111.6(8) . . ? C9 N3 C13 116.3(12) . . ? C9 N3 C10 103.8(11) . . ? C13 N3 C10 110.5(11) . . ? C14 N4 C18 115.9(6) . . ? C14 N4 Cu1 122.4(6) . . ? C18 N4 Cu1 121.6(6) . . ? N1 C1 C2 122.0(8) . . ? C3 C2 C1 119.0(8) . . ? C2 C3 C4 118.0(7) . . ? C2 C3 C6 119.0(9) . . ? C4 C3 C6 122.9(9) . . ? C5 C4 C3 120.0(8) . . ? C4 C5 N1 123.6(8) . . ? N2 C6 C3 112.9(6) . . ? N2 C7 C8 118.1(10) . . ? C9 C8 C7 119.0(10) . . ? N3 C9 C8 117.9(9) . . ? C11 C10 N3 117.6(12) . . ? C10 C11 C12 121.6(13) . . ? C11 C12 N2 113.5(13) . . ? N3 C13 C16 114.9(8) . 3_756 ? N4 C14 C15 123.3(8) . . ? C14 C15 C16 120.2(7) . . ? C17 C16 C15 116.1(7) . . ? C17 C16 C13 116.4(9) . 3_756 ? C15 C16 C13 127.3(8) . 3_756 ? C18 C17 C16 119.1(8) . . ? N4 C18 C17 125.3(8) . . ? O1 Cl3 O4 118.6(7) . . ? O1 Cl3 O2 99.3(7) . . ? O4 Cl3 O2 110.6(6) . . ? O1 Cl3 O3 114.4(7) . . ? O4 Cl3 O3 111.3(7) . . ? O2 Cl3 O3 100.1(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.771 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.084