# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_year 2009 _journal_page_first 434 _journal_volume ? _publ_contact_author_name 'Dr Jack Harrowfield' _publ_contact_author_email HARROWFIELD@ISIS.U-STRASBG.FR _publ_section_title ; Functionalised Azetidines as Ligands: Pyridyl-Complemented Coordination ; loop_ _publ_author_name 'Young Hoon Lee.' 'Jack Harrowfield' 'Yang Kim.' 'Woo Taik Lim.' 'Yu Cheol Park.' P.Thuery # Attachment 'yk52.cif' data_yk52 _database_code_depnum_ccdc_archive 'CCDC 678919' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 Cl Cu F6 N3 P' _chemical_formula_weight 435.24 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 'P 21/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 8.3218(4) _cell_length_b 23.3951(12) _cell_length_c 8.3949(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.409(3) _cell_angle_gamma 90.00 _cell_volume 1575.65(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 41724 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour 'translucent dark blue' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.835 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 1.719 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.666 _exptl_absorpt_correction_T_max 0.800 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 40 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and five \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 41724 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2971 _reflns_number_gt 2675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to N3 were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0284P)^2^+0.7127P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2971 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0216 _refine_ls_wR_factor_ref 0.0595 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.510 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.133 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 Cu Cu 0.85220(2) 0.402626(9) 0.83141(2) 0.01373(8) Uani 1 1 d . . . P1 P 0.84649(5) 0.40849(2) 0.33511(5) 0.01639(12) Uani 1 1 d . . . Cl1 Cl 1.12854(5) 0.408518(18) 0.94355(5) 0.01898(11) Uani 1 1 d . . . F1 F 0.85855(13) 0.38387(5) 0.51704(13) 0.0291(3) Uani 1 1 d . . . F2 F 0.83296(13) 0.34475(4) 0.26388(14) 0.0267(3) Uani 1 1 d . . . F3 F 0.83170(13) 0.43338(5) 0.15314(12) 0.0245(2) Uani 1 1 d . . . F4 F 0.85583(14) 0.47245(5) 0.40473(13) 0.0295(3) Uani 1 1 d . . . F5 F 0.64614(12) 0.41020(5) 0.29777(13) 0.0230(2) Uani 1 1 d . . . F6 F 1.04471(13) 0.40633(5) 0.37244(13) 0.0263(3) Uani 1 1 d . . . N1 N 0.82433(16) 0.31562(6) 0.81332(16) 0.0150(3) Uani 1 1 d . . . N2 N 0.60560(18) 0.40985(6) 0.79234(18) 0.0157(3) Uani 1 1 d . . . N3 N 0.84195(16) 0.48541(6) 0.77247(17) 0.0174(3) Uani 1 1 d . . . H3A H 0.8845 0.5080 0.8560 0.021 Uiso 1 1 d R . . H3B H 0.9037 0.4957 0.6994 0.021 Uiso 1 1 d R . . C1 C 0.9636(2) 0.28442(8) 0.8261(2) 0.0180(4) Uani 1 1 d . . . H1 H 1.0658 0.3032 0.8561 0.022 Uiso 1 1 calc R . . C2 C 0.9632(2) 0.22645(8) 0.7972(2) 0.0205(4) Uani 1 1 d . . . H2 H 1.0624 0.2068 0.8061 0.025 Uiso 1 1 calc R . . C3 C 0.8118(2) 0.19820(8) 0.7545(2) 0.0220(4) Uani 1 1 d . . . H3 H 0.8069 0.1591 0.7341 0.026 Uiso 1 1 calc R . . C4 C 0.6673(2) 0.22942(8) 0.7428(2) 0.0194(4) Uani 1 1 d . . . H4 H 0.5647 0.2109 0.7160 0.023 Uiso 1 1 calc R . . C5 C 0.6744(2) 0.28786(7) 0.7707(2) 0.0155(3) Uani 1 1 d . . . C6 C 0.5180(2) 0.32371(8) 0.7534(2) 0.0169(4) Uani 1 1 d . . . C7 C 0.5170(2) 0.37655(8) 0.6411(2) 0.0171(4) Uani 1 1 d . . . H7A H 0.5821 0.3715 0.5619 0.021 Uiso 1 1 calc R . . H7B H 0.4063 0.3908 0.5877 0.021 Uiso 1 1 calc R . . C8 C 0.5407(2) 0.36767(8) 0.8956(2) 0.0179(4) Uani 1 1 d . . . H8A H 0.4370 0.3792 0.9183 0.022 Uiso 1 1 calc R . . H8B H 0.6224 0.3564 0.9962 0.022 Uiso 1 1 calc R . . C9 C 0.3571(2) 0.28945(8) 0.7167(2) 0.0214(4) Uani 1 1 d . . . H9A H 0.3459 0.2677 0.6175 0.032 Uiso 1 1 calc R . . H9B H 0.2642 0.3150 0.7025 0.032 Uiso 1 1 calc R . . H9C H 0.3597 0.2640 0.8071 0.032 Uiso 1 1 calc R . . C10 C 0.5648(2) 0.47079(8) 0.7995(2) 0.0199(4) Uani 1 1 d . . . H10A H 0.5930 0.4839 0.9132 0.024 Uiso 1 1 calc R . . H10B H 0.4467 0.4770 0.7509 0.024 Uiso 1 1 calc R . . C11 C 0.6665(2) 0.50270(8) 0.7027(2) 0.0195(4) Uani 1 1 d . . . H11A H 0.6296 0.4928 0.5865 0.023 Uiso 1 1 calc R . . H11B H 0.6544 0.5436 0.7138 0.023 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 Cu 0.01211(12) 0.01151(14) 0.01745(13) -0.00012(8) 0.00374(9) 0.00010(8) P1 0.0177(2) 0.0149(3) 0.0173(2) 0.00007(17) 0.00593(19) -0.00104(17) Cl1 0.0131(2) 0.0169(2) 0.0257(2) -0.00232(16) 0.00281(17) 0.00014(16) F1 0.0279(6) 0.0379(7) 0.0220(5) 0.0095(5) 0.0076(5) 0.0000(5) F2 0.0262(6) 0.0155(6) 0.0385(6) -0.0042(5) 0.0088(5) 0.0014(4) F3 0.0277(6) 0.0272(6) 0.0192(5) 0.0032(4) 0.0073(4) -0.0043(5) F4 0.0374(6) 0.0190(6) 0.0299(6) -0.0076(5) 0.0052(5) -0.0018(5) F5 0.0171(5) 0.0254(6) 0.0273(6) 0.0016(4) 0.0076(4) 0.0017(4) F6 0.0173(6) 0.0312(7) 0.0302(6) 0.0038(5) 0.0060(5) -0.0023(4) N1 0.0154(7) 0.0145(8) 0.0160(7) 0.0005(6) 0.0056(6) 0.0004(6) N2 0.0149(7) 0.0147(8) 0.0182(7) -0.0005(6) 0.0055(6) 0.0001(6) N3 0.0161(7) 0.0139(8) 0.0205(7) -0.0001(6) 0.0020(6) -0.0010(6) C1 0.0173(8) 0.0172(10) 0.0204(8) -0.0001(7) 0.0062(7) 0.0002(7) C2 0.0209(9) 0.0177(10) 0.0235(9) 0.0006(7) 0.0070(7) 0.0040(7) C3 0.0291(10) 0.0131(9) 0.0231(9) -0.0014(7) 0.0059(8) 0.0001(8) C4 0.0200(9) 0.0178(9) 0.0192(9) -0.0002(7) 0.0031(7) -0.0039(7) C5 0.0167(8) 0.0167(9) 0.0132(8) 0.0006(7) 0.0041(6) -0.0008(7) C6 0.0150(8) 0.0176(9) 0.0187(9) -0.0007(7) 0.0054(7) -0.0026(7) C7 0.0147(8) 0.0173(10) 0.0190(8) -0.0009(7) 0.0035(7) -0.0015(7) C8 0.0163(8) 0.0196(10) 0.0199(9) 0.0009(7) 0.0084(7) 0.0000(7) C9 0.0163(9) 0.0211(10) 0.0270(9) 0.0000(8) 0.0063(7) -0.0039(7) C10 0.0166(9) 0.0170(10) 0.0258(9) -0.0008(7) 0.0049(7) 0.0034(7) C11 0.0179(9) 0.0141(10) 0.0240(9) 0.0016(7) 0.0010(7) 0.0026(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 Cu N3 1.9952(15) . ? Cu N2 1.9975(14) . ? Cu N1 2.0498(15) . ? Cu Cl1 2.2457(5) . ? Cu F1 2.6896(11) . ? P1 F6 1.5960(11) . ? P1 F2 1.5994(11) . ? P1 F4 1.6007(11) . ? P1 F3 1.6087(10) . ? P1 F1 1.6103(11) . ? P1 F5 1.6131(11) . ? N1 C1 1.350(2) . ? N1 C5 1.367(2) . ? N2 C10 1.470(2) . ? N2 C7 1.505(2) . ? N2 C8 1.505(2) . ? N3 C11 1.478(2) . ? N3 H3A 0.8750 . ? N3 H3B 0.9304 . ? C1 C2 1.378(3) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.386(3) . ? C4 H4 0.9300 . ? C5 C6 1.523(2) . ? C6 C9 1.520(2) . ? C6 C8 1.549(2) . ? C6 C7 1.553(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.516(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu N2 84.42(6) . . ? N3 Cu N1 161.64(6) . . ? N2 Cu N1 88.90(6) . . ? N3 Cu Cl1 90.91(4) . . ? N2 Cu Cl1 163.06(4) . . ? N1 Cu Cl1 100.09(4) . . ? N3 Cu F1 85.74(5) . . ? N2 Cu F1 98.04(5) . . ? N1 Cu F1 78.27(4) . . ? Cl1 Cu F1 97.84(3) . . ? F6 P1 F2 90.59(6) . . ? F6 P1 F4 90.60(6) . . ? F2 P1 F4 178.77(6) . . ? F6 P1 F3 90.70(6) . . ? F2 P1 F3 90.14(6) . . ? F4 P1 F3 89.57(6) . . ? F6 P1 F1 90.10(6) . . ? F2 P1 F1 90.09(6) . . ? F4 P1 F1 90.19(6) . . ? F3 P1 F1 179.17(6) . . ? F6 P1 F5 179.59(7) . . ? F2 P1 F5 89.08(6) . . ? F4 P1 F5 89.72(6) . . ? F3 P1 F5 89.55(6) . . ? F1 P1 F5 89.65(6) . . ? C1 N1 C5 117.95(15) . . ? C1 N1 Cu 116.95(11) . . ? C5 N1 Cu 124.65(11) . . ? C10 N2 C7 118.02(14) . . ? C10 N2 C8 119.35(13) . . ? C7 N2 C8 88.62(12) . . ? C10 N2 Cu 108.27(10) . . ? C7 N2 Cu 110.26(10) . . ? C8 N2 Cu 111.12(10) . . ? C11 N3 Cu 109.66(11) . . ? C11 N3 H3A 107.4 . . ? Cu N3 H3A 114.0 . . ? C11 N3 H3B 109.2 . . ? Cu N3 H3B 114.9 . . ? H3A N3 H3B 101.2 . . ? N1 C1 C2 123.83(16) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 118.36(16) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 118.65(17) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 120.67(16) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N1 C5 C4 120.52(15) . . ? N1 C5 C6 117.45(15) . . ? C4 C5 C6 122.03(15) . . ? C9 C6 C5 114.42(15) . . ? C9 C6 C8 115.26(14) . . ? C5 C6 C8 111.48(14) . . ? C9 C6 C7 115.76(14) . . ? C5 C6 C7 111.27(13) . . ? C8 C6 C7 85.35(13) . . ? N2 C7 C6 88.74(12) . . ? N2 C7 H7A 113.9 . . ? C6 C7 H7A 113.9 . . ? N2 C7 H7B 113.9 . . ? C6 C7 H7B 113.9 . . ? H7A C7 H7B 111.1 . . ? N2 C8 C6 88.89(12) . . ? N2 C8 H8A 113.8 . . ? C6 C8 H8A 113.8 . . ? N2 C8 H8B 113.8 . . ? C6 C8 H8B 113.8 . . ? H8A C8 H8B 111.1 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 106.74(14) . . ? N2 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? N2 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? N3 C11 C10 106.64(14) . . ? N3 C11 H11A 110.4 . . ? C10 C11 H11A 110.4 . . ? N3 C11 H11B 110.4 . . ? C10 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? # Attachment 'yk0613.cif' data_yk0613 _database_code_depnum_ccdc_archive 'CCDC 678920' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H17 Cl2 Cu N3' _chemical_formula_weight 325.72 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1460(5) _cell_length_b 9.9979(7) _cell_length_c 15.1346(11) _cell_angle_alpha 90.706(4) _cell_angle_beta 102.629(4) _cell_angle_gamma 104.858(4) _cell_volume 1301.85(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9324 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light blue' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 2.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.902 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method '\f scan with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9324 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4483 _reflns_number_gt 3992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to N atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0243P)^2^+2.5260P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4483 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.906 _refine_diff_density_max 0.492 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.081 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 0.75595(5) 0.61231(4) 0.38621(3) 0.01484(11) Uani 1 1 d . . . Cu2 Cu 0.76515(5) 1.01112(4) 0.88769(3) 0.01607(11) Uani 1 1 d . . . Cl1 Cl 0.52101(9) 0.65751(8) 0.41205(5) 0.01874(18) Uani 1 1 d . . . Cl2 Cl 0.99251(9) 0.71280(8) 0.49110(6) 0.02042(18) Uani 1 1 d . . . Cl3 Cl 1.0000 1.0000 1.0000 0.0211(2) Uani 1 2 d S . . Cl4 Cl 0.53266(9) 0.86181(8) 0.91630(6) 0.01889(18) Uani 1 1 d . . . Cl5 Cl 0.0000 0.5000 0.0000 0.0232(3) Uani 1 2 d S . . N1 N 0.7197(3) 0.4381(3) 0.45019(19) 0.0184(6) Uani 1 1 d . . . H1A H 0.8054 0.4277 0.4795 0.022 Uiso 1 1 d R . . H1B H 0.6507 0.4443 0.4834 0.022 Uiso 1 1 d R . . N2 N 0.7239(3) 0.4806(3) 0.27362(18) 0.0153(6) Uani 1 1 d . . . N3 N 0.7803(3) 0.7730(3) 0.30536(19) 0.0165(6) Uani 1 1 d . . . N4 N 0.7439(3) 1.1712(3) 0.95978(19) 0.0188(6) Uani 1 1 d . . . H4A H 0.6913 1.1393 1.0010 0.023 Uiso 1 1 d R . . H4B H 0.8412 1.2406 0.9830 0.023 Uiso 1 1 d R . . N5 N 0.7327(3) 1.1303(3) 0.78062(18) 0.0154(6) Uani 1 1 d . . . N6 N 0.7886(3) 0.8650(3) 0.80225(18) 0.0157(6) Uani 1 1 d . . . C1 C 0.6379(4) 0.3207(3) 0.3820(2) 0.0216(7) Uani 1 1 d . . . H1C H 0.5292 0.3194 0.3617 0.026 Uiso 1 1 calc R . . H1D H 0.6437 0.2336 0.4080 0.026 Uiso 1 1 calc R . . C2 C 0.7164(4) 0.3403(3) 0.3027(2) 0.0203(7) Uani 1 1 d . . . H2A H 0.8204 0.3280 0.3210 0.024 Uiso 1 1 calc R . . H2B H 0.6577 0.2722 0.2530 0.024 Uiso 1 1 calc R . . C3 C 0.8320(4) 0.5369(3) 0.2143(2) 0.0181(7) Uani 1 1 d . . . H3A H 0.8462 0.4666 0.1746 0.022 Uiso 1 1 calc R . . H3B H 0.9313 0.5963 0.2468 0.022 Uiso 1 1 calc R . . C4 C 0.5928(4) 0.5085(3) 0.2032(2) 0.0172(7) Uani 1 1 d . . . H4C H 0.5227 0.5477 0.2284 0.021 Uiso 1 1 calc R . . H4D H 0.5358 0.4298 0.1604 0.021 Uiso 1 1 calc R . . C5 C 0.7158(4) 0.6180(3) 0.1663(2) 0.0163(7) Uani 1 1 d . . . C6 C 0.6921(4) 0.6170(4) 0.0637(2) 0.0229(8) Uani 1 1 d . . . H6A H 0.6064 0.6546 0.0391 0.034 Uiso 1 1 calc R . . H6B H 0.6703 0.5234 0.0386 0.034 Uiso 1 1 calc R . . H6C H 0.7846 0.6723 0.0486 0.034 Uiso 1 1 calc R . . C7 C 0.7522(4) 0.7624(3) 0.2128(2) 0.0150(7) Uani 1 1 d . . . C8 C 0.7625(4) 0.8806(4) 0.1649(2) 0.0194(7) Uani 1 1 d . . . H8 H 0.7420 0.8727 0.1018 0.023 Uiso 1 1 calc R . . C9 C 0.8032(4) 1.0099(4) 0.2107(2) 0.0214(7) Uani 1 1 d . . . H9 H 0.8100 1.0893 0.1788 0.026 Uiso 1 1 calc R . . C10 C 0.8339(4) 1.0203(3) 0.3046(2) 0.0193(7) Uani 1 1 d . . . H10 H 0.8630 1.1063 0.3369 0.023 Uiso 1 1 calc R . . C11 C 0.8201(4) 0.8993(3) 0.3487(2) 0.0166(7) Uani 1 1 d . . . H11 H 0.8393 0.9057 0.4118 0.020 Uiso 1 1 calc R . . C12 C 0.6524(4) 1.2467(4) 0.8956(2) 0.0204(7) Uani 1 1 d . . . H12A H 0.6572 1.3359 0.9237 0.024 Uiso 1 1 calc R . . H12B H 0.5444 1.1936 0.8779 0.024 Uiso 1 1 calc R . . C13 C 0.7231(4) 1.2664(3) 0.8137(2) 0.0191(7) Uani 1 1 d . . . H13A H 0.6592 1.3049 0.7664 0.023 Uiso 1 1 calc R . . H13B H 0.8260 1.3302 0.8301 0.023 Uiso 1 1 calc R . . C14 C 0.6010(4) 1.0402(3) 0.7094(2) 0.0168(7) Uani 1 1 d . . . H14A H 0.5410 1.0918 0.6694 0.020 Uiso 1 1 calc R . . H14B H 0.5338 0.9654 0.7336 0.020 Uiso 1 1 calc R . . C15 C 0.8390(4) 1.1297(3) 0.7186(2) 0.0178(7) Uani 1 1 d . . . H15A H 0.9395 1.1180 0.7489 0.021 Uiso 1 1 calc R . . H15B H 0.8506 1.2082 0.6813 0.021 Uiso 1 1 calc R . . C16 C 0.7241(4) 0.9947(3) 0.6682(2) 0.0164(7) Uani 1 1 d . . . C17 C 0.6992(4) 0.9891(4) 0.5655(2) 0.0224(7) Uani 1 1 d . . . H17A H 0.7937 0.9857 0.5489 0.034 Uiso 1 1 calc R . . H17B H 0.6698 1.0703 0.5434 0.034 Uiso 1 1 calc R . . H17C H 0.6182 0.9078 0.5393 0.034 Uiso 1 1 calc R . . C18 C 0.7653(4) 0.8681(3) 0.7105(2) 0.0161(7) Uani 1 1 d . . . C19 C 0.7826(4) 0.7599(4) 0.6587(2) 0.0194(7) Uani 1 1 d . . . H19 H 0.7669 0.7631 0.5960 0.023 Uiso 1 1 calc R . . C20 C 0.8229(4) 0.6472(4) 0.6996(2) 0.0231(8) Uani 1 1 d . . . H20 H 0.8348 0.5749 0.6650 0.028 Uiso 1 1 calc R . . C21 C 0.8450(4) 0.6444(4) 0.7928(2) 0.0224(8) Uani 1 1 d . . . H21 H 0.8722 0.5702 0.8223 0.027 Uiso 1 1 calc R . . C22 C 0.8257(4) 0.7538(3) 0.8412(2) 0.0197(7) Uani 1 1 d . . . H22 H 0.8389 0.7508 0.9037 0.024 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 Cu1 0.0175(2) 0.0139(2) 0.0133(2) 0.00255(15) 0.00414(16) 0.00386(16) Cu2 0.0207(2) 0.0156(2) 0.0135(2) 0.00135(15) 0.00480(16) 0.00684(17) Cl1 0.0188(4) 0.0209(4) 0.0196(4) 0.0048(3) 0.0079(3) 0.0076(3) Cl2 0.0180(4) 0.0204(4) 0.0201(4) 0.0014(3) -0.0003(3) 0.0040(3) Cl3 0.0187(6) 0.0238(6) 0.0189(6) -0.0003(5) -0.0018(5) 0.0076(5) Cl4 0.0188(4) 0.0189(4) 0.0195(4) 0.0014(3) 0.0068(3) 0.0039(3) Cl5 0.0213(6) 0.0251(6) 0.0217(6) 0.0001(5) 0.0024(5) 0.0059(5) N1 0.0167(14) 0.0199(14) 0.0190(15) 0.0040(12) 0.0049(12) 0.0048(12) N2 0.0172(14) 0.0135(13) 0.0151(14) 0.0029(11) 0.0023(11) 0.0048(11) N3 0.0146(13) 0.0185(14) 0.0151(14) 0.0005(11) 0.0029(11) 0.0026(12) N4 0.0198(14) 0.0190(14) 0.0178(15) 0.0018(12) 0.0044(12) 0.0053(12) N5 0.0152(13) 0.0162(13) 0.0142(14) 0.0004(11) 0.0025(11) 0.0039(11) N6 0.0175(14) 0.0161(13) 0.0131(14) 0.0000(11) 0.0029(11) 0.0042(12) C1 0.0210(18) 0.0168(17) 0.0242(19) 0.0032(14) 0.0037(15) 0.0011(14) C2 0.0247(18) 0.0163(16) 0.0203(18) 0.0019(14) 0.0017(14) 0.0089(15) C3 0.0215(17) 0.0182(16) 0.0160(17) 0.0014(13) 0.0063(14) 0.0059(14) C4 0.0173(16) 0.0152(16) 0.0180(17) 0.0019(13) 0.0029(13) 0.0037(14) C5 0.0161(16) 0.0210(17) 0.0120(16) 0.0019(13) 0.0033(13) 0.0053(14) C6 0.0293(19) 0.0255(18) 0.0162(18) 0.0031(14) 0.0054(15) 0.0110(16) C7 0.0110(15) 0.0175(16) 0.0172(17) 0.0033(13) 0.0030(12) 0.0049(13) C8 0.0181(17) 0.0233(18) 0.0158(17) 0.0043(14) 0.0025(13) 0.0045(14) C9 0.0177(17) 0.0188(17) 0.029(2) 0.0097(15) 0.0047(15) 0.0075(14) C10 0.0183(17) 0.0141(16) 0.0246(18) -0.0009(14) 0.0024(14) 0.0051(14) C11 0.0164(16) 0.0183(16) 0.0158(17) -0.0011(13) 0.0039(13) 0.0056(14) C12 0.0213(17) 0.0196(17) 0.0195(18) -0.0033(14) 0.0018(14) 0.0071(15) C13 0.0231(18) 0.0160(16) 0.0194(18) 0.0022(13) 0.0036(14) 0.0082(14) C14 0.0158(16) 0.0158(16) 0.0158(16) 0.0006(13) -0.0008(13) 0.0025(13) C15 0.0192(17) 0.0190(16) 0.0159(17) 0.0020(13) 0.0057(13) 0.0049(14) C16 0.0169(16) 0.0193(16) 0.0124(16) 0.0011(13) 0.0033(13) 0.0036(14) C17 0.0271(19) 0.0231(18) 0.0140(18) 0.0011(14) 0.0030(14) 0.0028(15) C18 0.0130(15) 0.0185(16) 0.0157(17) 0.0000(13) 0.0043(13) 0.0018(13) C19 0.0174(16) 0.0221(17) 0.0166(17) -0.0037(14) 0.0026(13) 0.0027(14) C20 0.0232(18) 0.0208(18) 0.026(2) -0.0045(15) 0.0056(15) 0.0073(15) C21 0.0214(18) 0.0179(17) 0.026(2) 0.0044(14) 0.0012(15) 0.0060(15) C22 0.0212(17) 0.0183(17) 0.0181(17) 0.0022(13) 0.0031(14) 0.0038(14) _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 N1 1.992(3) . ? Cu1 N3 2.028(3) . ? Cu1 N2 2.062(3) . ? Cu1 Cl2 2.3568(9) . ? Cu1 Cl1 2.4156(9) . ? Cu2 N4 1.999(3) . ? Cu2 N6 2.022(3) . ? Cu2 N5 2.038(3) . ? Cu2 Cl4 2.3932(9) . ? Cu2 Cl3 2.4588(4) . ? Cu2 Cu2 4.9177(9) 2_777 ? Cl3 Cu2 2.4588(4) 2_777 ? N1 C1 1.478(4) . ? N2 C2 1.465(4) . ? N2 C3 1.489(4) . ? N2 C4 1.506(4) . ? N3 C11 1.341(4) . ? N3 C7 1.366(4) . ? N4 C12 1.484(4) . ? N5 C13 1.474(4) . ? N5 C15 1.493(4) . ? N5 C14 1.508(4) . ? N6 C22 1.350(4) . ? N6 C18 1.359(4) . ? C1 C2 1.518(5) . ? C3 C5 1.559(5) . ? C4 C5 1.560(4) . ? C5 C6 1.520(5) . ? C5 C7 1.522(5) . ? C7 C8 1.387(5) . ? C8 C9 1.382(5) . ? C9 C10 1.383(5) . ? C10 C11 1.380(5) . ? C12 C13 1.511(5) . ? C14 C16 1.558(4) . ? C15 C16 1.550(5) . ? C16 C17 1.519(4) . ? C16 C18 1.522(5) . ? C18 C19 1.390(5) . ? C19 C20 1.385(5) . ? C20 C21 1.383(5) . ? C21 C22 1.377(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 172.26(11) . . ? N1 Cu1 N2 84.20(11) . . ? N3 Cu1 N2 88.36(11) . . ? N1 Cu1 Cl2 92.43(9) . . ? N3 Cu1 Cl2 93.72(8) . . ? N2 Cu1 Cl2 126.67(8) . . ? N1 Cu1 Cl1 91.56(8) . . ? N3 Cu1 Cl1 89.62(8) . . ? N2 Cu1 Cl1 114.71(8) . . ? Cl2 Cu1 Cl1 118.59(3) . . ? N4 Cu2 N6 172.94(11) . . ? N4 Cu2 N5 84.43(11) . . ? N6 Cu2 N5 88.66(11) . . ? N4 Cu2 Cl4 92.02(9) . . ? N6 Cu2 Cl4 92.22(8) . . ? N5 Cu2 Cl4 115.18(8) . . ? N4 Cu2 Cl3 91.16(8) . . ? N6 Cu2 Cl3 92.39(8) . . ? N5 Cu2 Cl3 131.87(8) . . ? Cl4 Cu2 Cl3 112.85(3) . . ? Cu2 Cl3 Cu2 180.0 2_777 . ? C1 N1 Cu1 108.5(2) . . ? C2 N2 C3 117.7(3) . . ? C2 N2 C4 120.6(3) . . ? C3 N2 C4 89.1(2) . . ? C2 N2 Cu1 108.7(2) . . ? C3 N2 Cu1 112.7(2) . . ? C4 N2 Cu1 106.65(19) . . ? C11 N3 C7 118.8(3) . . ? C11 N3 Cu1 115.2(2) . . ? C7 N3 Cu1 125.9(2) . . ? C12 N4 Cu2 106.9(2) . . ? C13 N5 C15 117.4(3) . . ? C13 N5 C14 120.4(3) . . ? C15 N5 C14 89.0(2) . . ? C13 N5 Cu2 109.2(2) . . ? C15 N5 Cu2 113.7(2) . . ? C14 N5 Cu2 105.67(19) . . ? C22 N6 C18 118.5(3) . . ? C22 N6 Cu2 115.8(2) . . ? C18 N6 Cu2 125.7(2) . . ? N1 C1 C2 107.5(3) . . ? N2 C2 C1 108.3(3) . . ? N2 C3 C5 89.2(2) . . ? N2 C4 C5 88.5(2) . . ? C6 C5 C7 113.5(3) . . ? C6 C5 C3 115.3(3) . . ? C7 C5 C3 111.0(3) . . ? C6 C5 C4 116.4(3) . . ? C7 C5 C4 112.8(3) . . ? C3 C5 C4 84.7(2) . . ? N3 C7 C8 120.2(3) . . ? N3 C7 C5 117.3(3) . . ? C8 C7 C5 122.5(3) . . ? C9 C8 C7 120.1(3) . . ? C8 C9 C10 119.4(3) . . ? C11 C10 C9 118.0(3) . . ? N3 C11 C10 123.3(3) . . ? N4 C12 C13 106.9(3) . . ? N5 C13 C12 108.5(3) . . ? N5 C14 C16 88.4(2) . . ? N5 C15 C16 89.2(2) . . ? C17 C16 C18 114.1(3) . . ? C17 C16 C15 114.7(3) . . ? C18 C16 C15 110.4(3) . . ? C17 C16 C14 116.9(3) . . ? C18 C16 C14 112.2(3) . . ? C15 C16 C14 85.1(2) . . ? N6 C18 C19 120.4(3) . . ? N6 C18 C16 117.6(3) . . ? C19 C18 C16 122.0(3) . . ? C20 C19 C18 120.5(3) . . ? C21 C20 C19 118.7(3) . . ? C22 C21 C20 118.5(3) . . ? N6 C22 C21 123.3(3) . . ? 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 N1 H1B Cl1 0.90 2.51 3.329(3) 150.9 2_666 N1 H1A Cl2 0.84 2.56 3.323(3) 150.1 2_766 N4 H4A Cl4 0.88 2.62 3.419(3) 150.6 2_677 N4 H4B Cl5 0.97 2.61 3.470(3) 148.8 1_666 # Attachment 'YK06-18.cif' data_yk0618 _database_code_depnum_ccdc_archive 'CCDC 678921' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H17 Br2 Cu N3' _chemical_formula_weight 426.65 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2890(19) _cell_length_b 10.078(2) _cell_length_c 15.613(3) _cell_angle_alpha 91.05(3) _cell_angle_beta 101.83(3) _cell_angle_gamma 104.89(3) _cell_volume 1378.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5738 _cell_measurement_theta_min 1.45 _cell_measurement_theta_max 30.0 _exptl_crystal_description irregular _exptl_crystal_colour 'transparent green' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.998 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 7.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.564 _exptl_absorpt_correction_T_max 0.788 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'Synchrotron Radiation' _diffrn_radiation_source 'Synchrotron Radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5738 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5738 _reflns_number_gt 5564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _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^)+(0.1520P)^2^+3.5230P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5738 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1913 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.73695(6) 0.99132(6) 0.11741(3) 0.01084(18) Uani 1 1 d . . . Cu2 Cu 0.25807(6) 0.61848(6) 0.38212(3) 0.01034(18) Uani 1 1 d . . . Br1 Br 0.97771(5) 1.14861(5) 0.08487(3) 0.01394(17) Uani 1 1 d . . . Br2 Br 0.5000 1.0000 0.0000 0.0171(2) Uani 1 2 d S . . Br3 Br 0.01176(5) 0.66208(5) 0.41139(3) 0.01362(17) Uani 1 1 d . . . Br4 Br 0.50036(5) 0.72488(6) 0.49060(3) 0.01586(17) Uani 1 1 d . . . N1 N 0.7595(4) 0.8333(5) 0.0477(2) 0.0133(8) Uani 1 1 d . . . H1A H 0.6672 0.7774 0.0231 0.016 Uiso 1 1 calc R . . H1B H 0.8081 0.8639 0.0047 0.016 Uiso 1 1 calc R . . N2 N 0.7680(4) 0.8732(5) 0.2206(2) 0.0114(8) Uani 1 1 d . . . N3 N 0.7134(4) 1.1375(5) 0.1995(3) 0.0124(8) Uani 1 1 d . . . N4 N 0.2221(5) 0.4464(5) 0.4454(3) 0.0134(8) Uani 1 1 d . . . H4A H 0.3117 0.4341 0.4740 0.016 Uiso 1 1 calc R . . H4B H 0.1657 0.4527 0.4851 0.016 Uiso 1 1 calc R . . N5 N 0.2268(4) 0.4860(5) 0.2744(2) 0.0112(8) Uani 1 1 d . . . N6 N 0.2797(4) 0.7760(5) 0.3025(2) 0.0118(8) Uani 1 1 d . . . C1 C 0.8493(5) 0.7579(6) 0.1085(3) 0.0167(10) Uani 1 1 d . . . H1C H 0.9553 0.8105 0.1251 0.020 Uiso 1 1 calc R . . H1D H 0.8442 0.6695 0.0808 0.020 Uiso 1 1 calc R . . C2 C 0.7794(6) 0.7384(6) 0.1885(3) 0.0167(10) Uani 1 1 d . . . H2A H 0.6788 0.6742 0.1732 0.020 Uiso 1 1 calc R . . H2B H 0.8425 0.7012 0.2339 0.020 Uiso 1 1 calc R . . C3 C 0.8974(5) 0.9638(5) 0.2885(3) 0.0123(9) Uani 1 1 d . . . H3A H 0.9633 1.0377 0.2644 0.015 Uiso 1 1 calc R . . H3B H 0.9565 0.9133 0.3270 0.015 Uiso 1 1 calc R . . C4 C 0.6644(5) 0.8744(6) 0.2815(3) 0.0148(9) Uani 1 1 d . . . H4C H 0.6534 0.7971 0.3179 0.018 Uiso 1 1 calc R . . H4D H 0.5655 0.8856 0.2530 0.018 Uiso 1 1 calc R . . C5 C 0.7777(5) 1.0094(6) 0.3291(3) 0.0139(9) Uani 1 1 d . . . C6 C 0.8049(6) 1.0163(6) 0.4286(3) 0.0175(10) Uani 1 1 d . . . H6A H 0.8866 1.0960 0.4529 0.026 Uiso 1 1 calc R . . H6B H 0.8317 0.9349 0.4494 0.026 Uiso 1 1 calc R . . H6C H 0.7137 1.0224 0.4464 0.026 Uiso 1 1 calc R . . C7 C 0.7357(5) 1.1330(5) 0.2880(3) 0.0116(9) Uani 1 1 d . . . C8 C 0.7215(5) 1.2431(6) 0.3399(3) 0.0158(10) Uani 1 1 d . . . H8 H 0.7395 1.2413 0.4006 0.019 Uiso 1 1 calc R . . C9 C 0.6809(6) 1.3532(6) 0.3005(4) 0.0197(11) Uani 1 1 d . . . H9 H 0.6679 1.4242 0.3344 0.024 Uiso 1 1 calc R . . C10 C 0.6594(6) 1.3580(6) 0.2098(3) 0.0193(10) Uani 1 1 d . . . H10 H 0.6343 1.4325 0.1821 0.023 Uiso 1 1 calc R . . C11 C 0.6767(5) 1.2475(6) 0.1623(3) 0.0160(10) Uani 1 1 d . . . H11 H 0.6623 1.2494 0.1016 0.019 Uiso 1 1 calc R . . C12 C 0.1412(5) 0.3291(6) 0.3806(3) 0.0157(10) Uani 1 1 d . . . H12A H 0.0347 0.3282 0.3616 0.019 Uiso 1 1 calc R . . H12B H 0.1463 0.2430 0.4062 0.019 Uiso 1 1 calc R . . C13 C 0.2188(6) 0.3467(5) 0.3034(3) 0.0155(10) Uani 1 1 d . . . H13A H 0.3208 0.3345 0.3208 0.019 Uiso 1 1 calc R . . H13B H 0.1613 0.2784 0.2559 0.019 Uiso 1 1 calc R . . C14 C 0.0968(5) 0.5113(5) 0.2080(3) 0.0135(9) Uani 1 1 d . . . H14A H 0.0285 0.5505 0.2333 0.016 Uiso 1 1 calc R . . H14B H 0.0404 0.4320 0.1676 0.016 Uiso 1 1 calc R . . C15 C 0.3312(5) 0.5399(6) 0.2146(3) 0.0144(10) Uani 1 1 d . . . H15A H 0.3440 0.4691 0.1761 0.017 Uiso 1 1 calc R . . H15B H 0.4292 0.5995 0.2444 0.017 Uiso 1 1 calc R . . C16 C 0.2157(5) 0.6191(5) 0.1695(3) 0.0125(9) Uani 1 1 d . . . C17 C 0.1881(6) 0.6136(6) 0.0699(3) 0.0175(10) Uani 1 1 d . . . H17A H 0.1071 0.6550 0.0474 0.026 Uiso 1 1 calc R . . H17B H 0.1602 0.5194 0.0467 0.026 Uiso 1 1 calc R . . H17C H 0.2795 0.6629 0.0527 0.026 Uiso 1 1 calc R . . C18 C 0.2529(5) 0.7626(6) 0.2135(3) 0.0129(9) Uani 1 1 d . . . C19 C 0.2638(5) 0.8782(6) 0.1657(3) 0.0169(10) Uani 1 1 d . . . H19 H 0.2442 0.8682 0.1047 0.020 Uiso 1 1 calc R . . C20 C 0.3037(5) 1.0084(6) 0.2083(3) 0.0160(10) Uani 1 1 d . . . H20 H 0.3114 1.0858 0.1762 0.019 Uiso 1 1 calc R . . C21 C 0.3321(5) 1.0221(6) 0.2994(3) 0.0161(10) Uani 1 1 d . . . H21 H 0.3599 1.1084 0.3296 0.019 Uiso 1 1 calc R . . C22 C 0.3177(5) 0.9037(6) 0.3437(3) 0.0144(9) Uani 1 1 d . . . H22 H 0.3349 0.9120 0.4046 0.017 Uiso 1 1 calc R . . Br5 Br 0.5000 0.5000 0.0000 0.0183(2) Uani 1 2 d S . . 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 0.0096(3) 0.0140(4) 0.0081(3) -0.0002(2) -0.0015(2) 0.0045(2) Cu2 0.0082(3) 0.0128(4) 0.0083(3) 0.0013(2) -0.0015(2) 0.0022(2) Br1 0.0099(3) 0.0168(3) 0.0133(3) -0.00015(18) 0.00060(18) 0.00171(19) Br2 0.0089(3) 0.0241(5) 0.0148(3) -0.0011(3) -0.0071(2) 0.0058(3) Br3 0.0094(3) 0.0182(3) 0.0136(3) 0.00288(18) 0.00142(17) 0.00514(19) Br4 0.0084(3) 0.0194(3) 0.0154(3) 0.00062(19) -0.00576(18) 0.00251(19) N1 0.0087(17) 0.019(2) 0.0101(17) -0.0009(15) -0.0019(13) 0.0030(15) N2 0.0073(17) 0.015(2) 0.0100(17) 0.0002(14) -0.0015(13) 0.0030(14) N3 0.0082(17) 0.016(2) 0.0130(18) 0.0007(14) -0.0005(13) 0.0046(15) N4 0.0100(17) 0.016(2) 0.0122(17) 0.0011(15) -0.0009(14) 0.0018(15) N5 0.0052(16) 0.017(2) 0.0085(16) 0.0004(14) -0.0036(13) 0.0016(14) N6 0.0086(17) 0.015(2) 0.0104(17) 0.0010(14) -0.0005(13) 0.0029(14) C1 0.009(2) 0.022(3) 0.017(2) -0.0038(18) -0.0036(16) 0.0072(18) C2 0.015(2) 0.019(3) 0.014(2) 0.0021(18) -0.0042(17) 0.0068(19) C3 0.0040(18) 0.017(3) 0.0126(19) 0.0004(16) -0.0049(15) 0.0029(16) C4 0.009(2) 0.021(3) 0.012(2) 0.0009(17) 0.0019(16) 0.0017(17) C5 0.009(2) 0.021(3) 0.010(2) 0.0036(17) -0.0008(15) 0.0024(17) C6 0.021(2) 0.017(3) 0.009(2) 0.0014(17) -0.0042(17) 0.0007(19) C7 0.0035(18) 0.014(3) 0.015(2) -0.0021(16) -0.0010(15) 0.0006(15) C8 0.010(2) 0.021(3) 0.014(2) -0.0056(18) -0.0017(16) 0.0020(18) C9 0.014(2) 0.019(3) 0.026(3) -0.005(2) 0.0009(18) 0.0066(19) C10 0.013(2) 0.021(3) 0.021(2) 0.0006(19) -0.0016(18) 0.0056(19) C11 0.010(2) 0.020(3) 0.016(2) 0.0032(18) -0.0030(17) 0.0050(18) C12 0.0051(19) 0.013(3) 0.023(2) 0.0036(18) -0.0056(16) -0.0027(16) C13 0.014(2) 0.011(3) 0.017(2) -0.0012(17) -0.0050(17) 0.0033(17) C14 0.0066(19) 0.020(3) 0.0112(19) -0.0002(17) -0.0045(15) 0.0041(17) C15 0.008(2) 0.022(3) 0.013(2) 0.0024(18) -0.0005(16) 0.0063(18) C16 0.0086(19) 0.016(3) 0.013(2) 0.0007(17) -0.0021(15) 0.0056(17) C17 0.017(2) 0.024(3) 0.013(2) 0.0031(18) 0.0004(17) 0.010(2) C18 0.007(4) 0.010(4) 0.012(4) 0.000(3) 0.000(3) -0.001(3) C19 0.009(2) 0.026(3) 0.014(2) 0.0060(19) -0.0025(16) 0.0046(18) C20 0.009(2) 0.016(3) 0.021(2) 0.0065(18) -0.0021(17) 0.0022(17) C21 0.009(2) 0.015(3) 0.021(2) -0.0011(18) -0.0041(17) 0.0025(17) C22 0.010(2) 0.019(3) 0.013(2) -0.0023(17) -0.0018(16) 0.0038(17) Br5 0.0112(3) 0.0226(5) 0.0175(3) -0.0020(3) -0.0027(2) 0.0029(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 N1 1.991(4) . ? Cu1 N3 2.018(4) . ? Cu1 N2 2.037(4) . ? Cu1 Br1 2.5390(11) . ? Cu1 Br2 2.5812(10) . ? Cu2 N4 2.000(4) . ? Cu2 N6 2.029(4) . ? Cu2 N5 2.053(4) . ? Cu2 Br4 2.4929(13) . ? Cu2 Br3 2.5641(9) . ? Br2 Cu1 2.5812(10) 2_675 ? N1 C1 1.484(6) . ? N2 C2 1.476(7) . ? N2 C4 1.487(6) . ? N2 C3 1.510(6) . ? N3 C11 1.349(7) . ? N3 C7 1.357(6) . ? N4 C12 1.474(6) . ? N5 C13 1.472(7) . ? N5 C15 1.492(6) . ? N5 C14 1.501(6) . ? N6 C22 1.355(7) . ? N6 C18 1.358(6) . ? C1 C2 1.514(7) . ? C3 C5 1.546(6) . ? C4 C5 1.555(7) . ? C5 C7 1.514(7) . ? C5 C6 1.520(6) . ? C7 C8 1.411(7) . ? C8 C9 1.376(8) . ? C9 C10 1.392(7) . ? C10 C11 1.389(8) . ? C12 C13 1.517(7) . ? C14 C16 1.563(7) . ? C15 C16 1.560(7) . ? C16 C18 1.514(7) . ? C16 C17 1.521(6) . ? C18 C19 1.389(7) . ? C19 C20 1.385(8) . ? C20 C21 1.390(7) . ? C21 C22 1.381(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 N1 Cu1 N3 173.48(17) . . ? N1 Cu1 N2 84.30(17) . . ? N3 Cu1 N2 89.26(17) . . ? N1 Cu1 Br1 91.53(12) . . ? N3 Cu1 Br1 92.20(12) . . ? N2 Cu1 Br1 115.90(11) . . ? N1 Cu1 Br2 89.71(12) . . ? N3 Cu1 Br2 93.94(12) . . ? N2 Cu1 Br2 132.89(11) . . ? Br1 Cu1 Br2 110.93(3) . . ? N4 Cu2 N6 172.06(17) . . ? N4 Cu2 N5 84.13(17) . . ? N6 Cu2 N5 88.43(16) . . ? N4 Cu2 Br4 91.71(12) . . ? N6 Cu2 Br4 95.05(12) . . ? N5 Cu2 Br4 127.72(11) . . ? N4 Cu2 Br3 90.29(12) . . ? N6 Cu2 Br3 90.26(12) . . ? N5 Cu2 Br3 114.46(11) . . ? Br4 Cu2 Br3 117.66(3) . . ? Cu1 Br2 Cu1 180.00(3) 2_675 . ? C1 N1 Cu1 107.5(3) . . ? C2 N2 C4 117.9(4) . . ? C2 N2 C3 120.0(4) . . ? C4 N2 C3 88.9(3) . . ? C2 N2 Cu1 109.4(3) . . ? C4 N2 Cu1 113.9(3) . . ? C3 N2 Cu1 105.2(3) . . ? C11 N3 C7 119.2(4) . . ? C11 N3 Cu1 116.3(3) . . ? C7 N3 Cu1 124.4(4) . . ? C12 N4 Cu2 108.5(3) . . ? C13 N5 C15 118.0(4) . . ? C13 N5 C14 119.9(4) . . ? C15 N5 C14 89.2(3) . . ? C13 N5 Cu2 108.7(3) . . ? C15 N5 Cu2 113.3(3) . . ? C14 N5 Cu2 106.3(3) . . ? C22 N6 C18 119.0(4) . . ? C22 N6 Cu2 115.4(3) . . ? C18 N6 Cu2 125.5(4) . . ? N1 C1 C2 106.6(4) . . ? N2 C2 C1 108.6(4) . . ? N2 C3 C5 88.5(3) . . ? N2 C4 C5 89.0(3) . . ? C7 C5 C6 114.7(4) . . ? C7 C5 C3 112.5(4) . . ? C6 C5 C3 116.1(4) . . ? C7 C5 C4 109.9(4) . . ? C6 C5 C4 114.9(4) . . ? C3 C5 C4 85.2(4) . . ? N3 C7 C8 120.0(5) . . ? N3 C7 C5 118.8(4) . . ? C8 C7 C5 121.2(4) . . ? C9 C8 C7 119.9(4) . . ? C8 C9 C10 119.9(5) . . ? C11 C10 C9 117.5(5) . . ? N3 C11 C10 123.4(4) . . ? N4 C12 C13 107.2(4) . . ? N5 C13 C12 108.4(4) . . ? N5 C14 C16 88.5(3) . . ? N5 C15 C16 88.9(3) . . ? C18 C16 C17 114.4(4) . . ? C18 C16 C15 110.8(4) . . ? C17 C16 C15 115.1(4) . . ? C18 C16 C14 112.9(4) . . ? C17 C16 C14 115.6(4) . . ? C15 C16 C14 84.6(4) . . ? N6 C18 C19 120.3(5) . . ? N6 C18 C16 117.9(4) . . ? C19 C18 C16 121.8(4) . . ? C20 C19 C18 120.3(4) . . ? C19 C20 C21 119.4(5) . . ? C22 C21 C20 118.0(5) . . ? N6 C22 C21 123.0(4) . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.683 _refine_diff_density_min -3.436 _refine_diff_density_rms 0.423 # Attachment 'YK06-19.cif' data_yk0619 _database_code_depnum_ccdc_archive 'CCDC 678922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H42 Cl3 Cu2 N6 O13' _chemical_formula_weight 940.14 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.812(2) _cell_length_b 13.045(3) _cell_length_c 15.543(3) _cell_angle_alpha 92.12(3) _cell_angle_beta 101.22(3) _cell_angle_gamma 112.10(3) _cell_volume 1977.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10123 _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 270.34 _exptl_crystal_description irregular _exptl_crystal_colour Blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 966 _exptl_absorpt_coefficient_mu 1.347 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.69996 _diffrn_radiation_type 'Synchrotron radiation' _diffrn_radiation_source 'Synchrotron radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10123 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 30.34 _reflns_number_total 10123 _reflns_number_gt 7394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _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^)+(0.1618P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.036(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10123 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2290 _refine_ls_wR_factor_gt 0.2130 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.045 _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 0.67518(4) 0.91582(4) 0.23807(3) 0.03698(16) Uani 1 1 d . . . Cu2 Cu 0.20040(5) 0.43675(4) 0.25211(3) 0.03931(16) Uani 1 1 d . . . O1 O 0.8067(3) 0.9038(2) 0.16978(17) 0.0436(6) Uani 1 1 d . . . O2 O 0.8488(3) 1.0833(2) 0.1680(2) 0.0509(7) Uani 1 1 d . . . O3 O 0.6262(4) 0.7493(3) 0.2854(2) 0.0626(8) Uani 1 1 d . . . H3A' H 0.5350 0.7000 0.2747 0.075 Uiso 1 1 calc R . . O4 O 0.2403(3) 0.4227(2) 0.13308(18) 0.0480(6) Uani 1 1 d . . . O5 O 0.4229(3) 0.5584(3) 0.2125(2) 0.0570(8) Uani 1 1 d . . . O6 O 0.7299(13) 0.4503(11) 0.3650(5) 0.246(6) Uani 1 1 d . . . O7 O 0.7821(8) 0.4581(13) 0.2416(8) 0.317(9) Uani 1 1 d . . . O8 O 0.5679(4) 0.3516(6) 0.2377(3) 0.1153(19) Uani 1 1 d . . . O9 O 0.7581(6) 0.3108(5) 0.2989(6) 0.163(3) Uani 1 1 d . . . O10 O 0.1227(8) -0.0523(4) 0.3886(4) 0.134(2) Uani 1 1 d . . . O11 O 0.3271(6) 0.0958(6) 0.4010(4) 0.134(2) Uani 1 1 d . . . O12 O 0.1278(4) 0.1035(4) 0.3225(3) 0.0802(11) Uani 1 1 d . . . O13 O 0.1733(7) 0.1105(5) 0.4733(3) 0.1104(17) Uani 1 1 d . . . N1 N 0.5214(4) 0.8620(3) 0.1258(2) 0.0465(7) Uani 1 1 d . . . N2 N 0.5624(4) 0.9791(3) 0.2932(2) 0.0480(7) Uani 1 1 d . . . N3 N 0.8225(3) 0.9958(3) 0.3469(2) 0.0451(7) Uani 1 1 d . . . H3A H 0.8308 0.9468 0.3846 0.054 Uiso 1 1 calc R . . H3B H 0.9035 1.0298 0.3321 0.054 Uiso 1 1 calc R . . N4 N 0.1213(3) 0.5560(3) 0.2253(2) 0.0447(7) Uani 1 1 d . . . N5 N 0.2178(3) 0.4770(3) 0.3817(2) 0.0427(7) Uani 1 1 d . . . N6 N 0.3024(4) 0.3397(3) 0.2967(3) 0.0534(8) Uani 1 1 d . . . H6A H 0.2436 0.2681 0.2912 0.064 Uiso 1 1 calc R . . H6B H 0.3655 0.3441 0.2652 0.064 Uiso 1 1 calc R . . C1 C 0.5318(5) 0.7952(4) 0.0630(3) 0.0563(10) Uani 1 1 d . . . H1 H 0.6055 0.7734 0.0737 0.068 Uiso 1 1 calc R . . C2 C 0.4388(6) 0.7568(5) -0.0170(3) 0.0732(14) Uani 1 1 d . . . H2 H 0.4471 0.7075 -0.0581 0.088 Uiso 1 1 calc R . . C3 C 0.3339(6) 0.7929(6) -0.0347(4) 0.0802(17) Uani 1 1 d . . . H3 H 0.2726 0.7716 -0.0895 0.096 Uiso 1 1 calc R . . C4 C 0.3201(6) 0.8597(5) 0.0281(3) 0.0712(14) Uani 1 1 d . . . H4 H 0.2479 0.8833 0.0167 0.085 Uiso 1 1 calc R . . C5 C 0.4129(4) 0.8937(4) 0.1098(3) 0.0504(9) Uani 1 1 d . . . C6 C 0.3989(5) 0.9639(4) 0.1842(3) 0.0551(10) Uani 1 1 d . . . C7 C 0.4122(5) 0.9105(4) 0.2723(3) 0.0573(10) Uani 1 1 d . . . H7A H 0.3644 0.9285 0.3134 0.069 Uiso 1 1 calc R . . H7B H 0.3892 0.8309 0.2636 0.069 Uiso 1 1 calc R . . C8 C 0.5366(5) 1.0577(4) 0.2304(3) 0.0568(11) Uani 1 1 d . . . H8A H 0.6017 1.0817 0.1929 0.068 Uiso 1 1 calc R . . H8B H 0.5271 1.1210 0.2588 0.068 Uiso 1 1 calc R . . C9 C 0.2788(6) 0.9984(6) 0.1617(4) 0.0817(18) Uani 1 1 d . . . H9A H 0.2769 1.0423 0.2120 0.123 Uiso 1 1 calc R . . H9B H 0.1951 0.9332 0.1458 0.123 Uiso 1 1 calc R . . H9C H 0.2880 1.0417 0.1130 0.123 Uiso 1 1 calc R . . C10 C 0.6328(5) 1.0245(5) 0.3845(3) 0.0619(12) Uani 1 1 d . . . H10A H 0.6145 0.9654 0.4222 0.074 Uiso 1 1 calc R . . H10B H 0.6002 1.0789 0.4048 0.074 Uiso 1 1 calc R . . C11 C 0.7838(5) 1.0788(4) 0.3890(3) 0.0593(11) Uani 1 1 d . . . H11A H 0.8041 1.1443 0.3581 0.071 Uiso 1 1 calc R . . H11B H 0.8343 1.1013 0.4501 0.071 Uiso 1 1 calc R . . C12 C 0.8599(4) 0.9969(3) 0.1421(2) 0.0404(7) Uani 1 1 d . . . C13 C 0.9349(4) 0.9984(3) 0.0696(2) 0.0380(7) Uani 1 1 d . . . C14 C 1.0255(4) 1.0994(3) 0.0509(2) 0.0428(8) Uani 1 1 d . . . H14 H 1.0428 1.1657 0.0847 0.051 Uiso 1 1 calc R . . C15 C 0.9099(4) 0.8998(3) 0.0188(2) 0.0413(7) Uani 1 1 d . . . H15 H 0.8496 0.8325 0.0314 0.050 Uiso 1 1 calc R . . C16 C 0.0759(5) 0.5624(5) 0.1393(3) 0.0606(11) Uani 1 1 d . . . H16 H 0.0820 0.5133 0.0970 0.073 Uiso 1 1 calc R . . C17 C 0.0207(6) 0.6385(5) 0.1109(3) 0.0716(14) Uani 1 1 d . . . H17 H -0.0121 0.6392 0.0511 0.086 Uiso 1 1 calc R . . C18 C 0.0158(6) 0.7125(5) 0.1731(4) 0.0776(16) Uani 1 1 d . . . H18 H -0.0191 0.7657 0.1562 0.093 Uiso 1 1 calc R . . C19 C 0.0636(5) 0.7074(4) 0.2622(3) 0.0624(12) Uani 1 1 d . . . H19 H 0.0613 0.7578 0.3051 0.075 Uiso 1 1 calc R . . C20 C 0.1136(4) 0.6286(3) 0.2865(3) 0.0448(8) Uani 1 1 d . . . C21 C 0.1643(5) 0.6185(4) 0.3832(3) 0.0510(9) Uani 1 1 d . . . C22 C 0.0996(5) 0.4964(4) 0.4032(3) 0.0517(9) Uani 1 1 d . . . H22A H 0.0933 0.4899 0.4643 0.062 Uiso 1 1 calc R . . H22B H 0.0126 0.4524 0.3632 0.062 Uiso 1 1 calc R . . C23 C 0.2987(5) 0.5998(4) 0.3995(3) 0.0521(10) Uani 1 1 d . . . H23A H 0.3540 0.6292 0.3570 0.063 Uiso 1 1 calc R . . H23B H 0.3531 0.6247 0.4595 0.063 Uiso 1 1 calc R . . C24 C 0.1594(8) 0.7075(5) 0.4478(4) 0.0822(17) Uani 1 1 d . . . H24A H 0.1922 0.6965 0.5073 0.123 Uiso 1 1 calc R . . H24B H 0.0667 0.7019 0.4403 0.123 Uiso 1 1 calc R . . H24C H 0.2161 0.7801 0.4364 0.123 Uiso 1 1 calc R . . C25 C 0.2667(5) 0.4025(4) 0.4330(3) 0.0592(11) Uani 1 1 d . . . H25A H 0.1907 0.3330 0.4335 0.071 Uiso 1 1 calc R . . H25B H 0.3089 0.4368 0.4935 0.071 Uiso 1 1 calc R . . C26 C 0.3697(5) 0.3809(4) 0.3908(3) 0.0611(11) Uani 1 1 d . . . H26A H 0.4504 0.4490 0.3959 0.073 Uiso 1 1 calc R . . H26B H 0.3973 0.3256 0.4194 0.073 Uiso 1 1 calc R . . C27 C 0.3618(4) 0.4937(3) 0.1427(2) 0.0430(8) Uani 1 1 d . . . C28 C 0.4334(4) 0.4952(3) 0.0686(2) 0.0423(8) Uani 1 1 d . . . C29 C 0.5754(4) 0.5470(4) 0.0845(3) 0.0475(9) Uani 1 1 d . . . H29 H 0.6262 0.5790 0.1413 0.057 Uiso 1 1 calc R . . C30 C 0.3589(4) 0.4490(4) -0.0162(3) 0.0488(9) Uani 1 1 d . . . H30 H 0.2638 0.4151 -0.0272 0.059 Uiso 1 1 calc R . . C31 C 0.7278(9) 0.7154(6) 0.3310(5) 0.117(3) Uani 1 1 d . . . H31A H 0.6852 0.6411 0.3454 0.176 Uiso 1 1 calc R . . H31B H 0.7771 0.7652 0.3843 0.176 Uiso 1 1 calc R . . H31C H 0.7900 0.7167 0.2942 0.176 Uiso 1 1 calc R . . Cl1 Cl 0.70052(12) 0.38905(10) 0.28970(8) 0.0606(3) Uani 1 1 d . . . Cl2 Cl 0.18956(13) 0.06448(10) 0.39677(8) 0.0609(3) Uani 1 1 d . . . Cl3 Cl -0.0166(4) 0.3044(3) 0.2190(3) 0.1966(16) 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 0.0383(3) 0.0381(2) 0.0336(2) 0.00155(16) 0.00681(16) 0.01476(18) Cu2 0.0401(3) 0.0406(3) 0.0385(2) 0.00051(17) 0.01415(18) 0.01494(19) O1 0.0494(16) 0.0410(13) 0.0414(13) 0.0054(10) 0.0153(11) 0.0164(11) O2 0.0617(18) 0.0415(14) 0.0566(16) 0.0055(12) 0.0233(13) 0.0231(13) O3 0.066(2) 0.0379(15) 0.071(2) 0.0102(14) 0.0028(15) 0.0107(13) O4 0.0422(15) 0.0545(16) 0.0447(14) -0.0036(11) 0.0198(11) 0.0121(12) O5 0.0571(18) 0.0539(17) 0.0483(15) -0.0083(13) 0.0230(13) 0.0047(13) O6 0.340(13) 0.385(16) 0.093(5) -0.082(7) -0.034(6) 0.280(13) O7 0.108(6) 0.443(19) 0.262(12) 0.221(13) 0.003(6) -0.041(8) O8 0.058(3) 0.188(6) 0.104(4) 0.011(4) 0.011(2) 0.058(3) O9 0.098(4) 0.080(4) 0.293(10) -0.019(5) -0.016(5) 0.047(3) O10 0.219(7) 0.059(3) 0.110(4) 0.007(3) 0.006(4) 0.055(4) O11 0.086(4) 0.189(7) 0.137(5) 0.015(5) 0.007(3) 0.074(4) O12 0.075(3) 0.087(3) 0.075(2) 0.031(2) 0.0107(19) 0.029(2) O13 0.186(6) 0.099(4) 0.074(3) 0.010(2) 0.042(3) 0.080(4) N1 0.0526(19) 0.0437(17) 0.0396(15) 0.0003(12) 0.0010(13) 0.0198(14) N2 0.054(2) 0.056(2) 0.0398(16) 0.0032(14) 0.0083(13) 0.0290(16) N3 0.0431(18) 0.0483(18) 0.0393(15) 0.0013(13) 0.0048(12) 0.0155(14) N4 0.0500(19) 0.0462(17) 0.0375(15) 0.0040(12) 0.0108(13) 0.0180(14) N5 0.0485(18) 0.0448(17) 0.0389(15) 0.0042(12) 0.0120(13) 0.0219(14) N6 0.054(2) 0.0496(19) 0.067(2) 0.0090(16) 0.0258(17) 0.0259(16) C1 0.061(3) 0.052(2) 0.049(2) -0.0077(17) 0.0017(18) 0.022(2) C2 0.086(4) 0.074(3) 0.047(2) -0.010(2) -0.002(2) 0.028(3) C3 0.083(4) 0.089(4) 0.052(3) -0.005(3) -0.016(2) 0.031(3) C4 0.063(3) 0.086(4) 0.058(3) 0.005(3) -0.009(2) 0.033(3) C5 0.047(2) 0.054(2) 0.047(2) 0.0082(17) 0.0030(16) 0.0204(18) C6 0.052(3) 0.068(3) 0.053(2) 0.011(2) 0.0077(18) 0.033(2) C7 0.049(3) 0.072(3) 0.058(2) 0.014(2) 0.0187(19) 0.028(2) C8 0.069(3) 0.052(2) 0.055(2) 0.0040(18) 0.007(2) 0.034(2) C9 0.076(4) 0.117(5) 0.075(3) 0.014(3) 0.009(3) 0.066(4) C10 0.068(3) 0.087(3) 0.041(2) -0.009(2) 0.0070(19) 0.045(3) C11 0.080(3) 0.050(2) 0.043(2) -0.0101(17) -0.001(2) 0.029(2) C12 0.0390(19) 0.0455(19) 0.0375(16) 0.0046(14) 0.0073(13) 0.0182(15) C13 0.0379(18) 0.0413(18) 0.0387(16) 0.0072(13) 0.0094(13) 0.0192(14) C14 0.048(2) 0.0393(18) 0.0434(18) 0.0053(14) 0.0127(15) 0.0179(15) C15 0.041(2) 0.0387(17) 0.0443(18) 0.0078(14) 0.0096(14) 0.0160(14) C16 0.067(3) 0.074(3) 0.043(2) 0.004(2) 0.0048(19) 0.035(2) C17 0.080(4) 0.092(4) 0.052(3) 0.016(3) 0.007(2) 0.047(3) C18 0.077(4) 0.078(4) 0.087(4) 0.029(3) 0.010(3) 0.043(3) C19 0.072(3) 0.051(2) 0.068(3) 0.000(2) 0.011(2) 0.031(2) C20 0.046(2) 0.0431(19) 0.0454(19) 0.0041(15) 0.0108(15) 0.0169(16) C21 0.065(3) 0.047(2) 0.0446(19) -0.0020(16) 0.0152(18) 0.0255(19) C22 0.062(3) 0.055(2) 0.046(2) 0.0064(17) 0.0234(18) 0.025(2) C23 0.056(3) 0.045(2) 0.045(2) -0.0030(16) 0.0020(17) 0.0139(18) C24 0.131(5) 0.070(3) 0.060(3) -0.009(2) 0.020(3) 0.058(4) C25 0.079(3) 0.058(3) 0.045(2) 0.0116(18) 0.010(2) 0.034(2) C26 0.054(3) 0.067(3) 0.070(3) 0.014(2) 0.009(2) 0.034(2) C27 0.043(2) 0.0451(19) 0.0434(18) 0.0032(14) 0.0197(15) 0.0158(15) C28 0.045(2) 0.0455(19) 0.0389(17) 0.0043(14) 0.0165(14) 0.0167(15) C29 0.041(2) 0.056(2) 0.0425(18) -0.0013(16) 0.0107(15) 0.0151(17) C30 0.041(2) 0.057(2) 0.0432(19) 0.0003(16) 0.0142(15) 0.0112(16) C31 0.153(7) 0.059(4) 0.107(5) 0.000(3) -0.046(5) 0.043(4) Cl1 0.0579(7) 0.0609(7) 0.0686(7) 0.0026(5) 0.0110(5) 0.0315(5) Cl2 0.0723(8) 0.0619(7) 0.0578(6) 0.0113(5) 0.0156(5) 0.0358(6) Cl3 0.127(2) 0.152(3) 0.283(5) -0.025(3) 0.050(3) 0.027(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 Cu1 O1 1.979(3) . ? Cu1 N2 2.003(3) . ? Cu1 N3 2.015(3) . ? Cu1 N1 2.050(3) . ? Cu1 O3 2.223(3) . ? Cu2 O4 1.997(3) . ? Cu2 N5 2.017(3) . ? Cu2 N6 2.029(4) . ? Cu2 N4 2.058(3) . ? Cu2 Cl3 2.273(4) . ? O1 C12 1.266(5) . ? O2 C12 1.238(5) . ? O3 C31 1.411(7) . ? O4 C27 1.267(5) . ? O5 C27 1.249(5) . ? O6 Cl1 1.306(7) . ? O7 Cl1 1.362(9) . ? O8 Cl1 1.393(4) . ? O9 Cl1 1.380(5) . ? O10 Cl2 1.407(5) . ? O11 Cl2 1.374(6) . ? O12 Cl2 1.427(4) . ? O13 Cl2 1.383(5) . ? N1 C1 1.334(5) . ? N1 C5 1.368(5) . ? N2 C10 1.457(5) . ? N2 C7 1.491(6) . ? N2 C8 1.506(5) . ? N3 C11 1.474(5) . ? N4 C16 1.349(5) . ? N4 C20 1.354(5) . ? N5 C25 1.462(5) . ? N5 C22 1.487(5) . ? N5 C23 1.493(5) . ? N6 C26 1.480(6) . ? C1 C2 1.377(6) . ? C2 C3 1.369(8) . ? C3 C4 1.353(8) . ? C4 C5 1.394(6) . ? C5 C6 1.514(6) . ? C6 C9 1.512(6) . ? C6 C8 1.542(7) . ? C6 C7 1.564(6) . ? C10 C11 1.502(8) . ? C12 C13 1.507(5) . ? C13 C15 1.390(5) . ? C13 C14 1.395(5) . ? C14 C15 1.397(5) 2_775 ? C15 C14 1.397(5) 2_775 ? C16 C17 1.382(7) . ? C17 C18 1.363(8) . ? C18 C19 1.394(8) . ? C19 C20 1.363(6) . ? C20 C21 1.525(6) . ? C21 C24 1.531(6) . ? C21 C23 1.537(6) . ? C21 C22 1.550(6) . ? C25 C26 1.502(7) . ? C27 C28 1.503(5) . ? C28 C30 1.383(5) . ? C28 C29 1.391(6) . ? C29 C30 1.381(5) 2_665 ? C30 C29 1.381(5) 2_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 O1 Cu1 N2 160.55(14) . . ? O1 Cu1 N3 93.55(13) . . ? N2 Cu1 N3 84.26(14) . . ? O1 Cu1 N1 90.32(13) . . ? N2 Cu1 N1 88.83(14) . . ? N3 Cu1 N1 169.45(14) . . ? O1 Cu1 O3 95.94(13) . . ? N2 Cu1 O3 103.49(15) . . ? N3 Cu1 O3 93.85(14) . . ? N1 Cu1 O3 95.52(13) . . ? O4 Cu2 N5 163.70(13) . . ? O4 Cu2 N6 90.49(14) . . ? N5 Cu2 N6 83.92(14) . . ? O4 Cu2 N4 95.11(13) . . ? N5 Cu2 N4 88.36(13) . . ? N6 Cu2 N4 169.71(15) . . ? O4 Cu2 Cl3 96.94(15) . . ? N5 Cu2 Cl3 99.04(16) . . ? N6 Cu2 Cl3 98.87(16) . . ? N4 Cu2 Cl3 89.03(15) . . ? C12 O1 Cu1 107.5(2) . . ? C31 O3 Cu1 122.7(4) . . ? C27 O4 Cu2 103.4(2) . . ? C1 N1 C5 118.2(4) . . ? C1 N1 Cu1 117.3(3) . . ? C5 N1 Cu1 124.4(3) . . ? C10 N2 C7 119.2(4) . . ? C10 N2 C8 118.1(4) . . ? C7 N2 C8 88.9(3) . . ? C10 N2 Cu1 109.2(3) . . ? C7 N2 Cu1 115.6(3) . . ? C8 N2 Cu1 103.8(3) . . ? C11 N3 Cu1 108.2(3) . . ? C16 N4 C20 118.1(4) . . ? C16 N4 Cu2 116.5(3) . . ? C20 N4 Cu2 125.4(3) . . ? C25 N5 C22 117.5(3) . . ? C25 N5 C23 119.4(4) . . ? C22 N5 C23 88.5(3) . . ? C25 N5 Cu2 109.4(3) . . ? C22 N5 Cu2 114.9(3) . . ? C23 N5 Cu2 105.4(2) . . ? C26 N6 Cu2 107.5(3) . . ? N1 C1 C2 123.2(5) . . ? C3 C2 C1 118.6(5) . . ? C4 C3 C2 119.4(5) . . ? C3 C4 C5 120.7(5) . . ? N1 C5 C4 119.8(4) . . ? N1 C5 C6 117.2(3) . . ? C4 C5 C6 123.1(4) . . ? C5 C6 C9 114.6(4) . . ? C5 C6 C8 112.4(4) . . ? C9 C6 C8 115.4(5) . . ? C5 C6 C7 110.4(4) . . ? C9 C6 C7 115.6(4) . . ? C8 C6 C7 85.0(3) . . ? N2 C7 C6 88.9(3) . . ? N2 C8 C6 89.2(3) . . ? N2 C10 C11 108.5(4) . . ? N3 C11 C10 107.0(4) . . ? O2 C12 O1 124.2(4) . . ? O2 C12 C13 119.4(3) . . ? O1 C12 C13 116.3(3) . . ? C15 C13 C14 119.7(3) . . ? C15 C13 C12 120.1(3) . . ? C14 C13 C12 120.1(3) . . ? C15 C14 C13 119.6(3) 2_775 . ? C13 C15 C14 120.7(3) . 2_775 ? N4 C16 C17 123.2(5) . . ? C18 C17 C16 118.1(5) . . ? C17 C18 C19 119.2(5) . . ? C20 C19 C18 120.1(5) . . ? N4 C20 C19 121.2(4) . . ? N4 C20 C21 116.9(3) . . ? C19 C20 C21 122.0(4) . . ? C20 C21 C24 113.5(4) . . ? C20 C21 C23 112.5(3) . . ? C24 C21 C23 116.0(4) . . ? C20 C21 C22 111.1(4) . . ? C24 C21 C22 116.0(4) . . ? C23 C21 C22 84.7(3) . . ? N5 C22 C21 89.1(3) . . ? N5 C23 C21 89.4(3) . . ? N5 C25 C26 108.1(4) . . ? N6 C26 C25 106.9(4) . . ? O5 C27 O4 121.4(3) . . ? O5 C27 C28 120.5(3) . . ? O4 C27 C28 118.0(3) . . ? C30 C28 C29 119.5(3) . . ? C30 C28 C27 120.6(4) . . ? C29 C28 C27 119.9(3) . . ? C30 C29 C28 120.0(4) 2_665 . ? C29 C30 C28 120.5(4) 2_665 . ? O6 Cl1 O7 103.7(10) . . ? O6 Cl1 O9 110.3(5) . . ? O7 Cl1 O9 99.6(8) . . ? O6 Cl1 O8 119.0(5) . . ? O7 Cl1 O8 105.6(5) . . ? O9 Cl1 O8 115.8(4) . . ? O11 Cl2 O13 108.7(4) . . ? O11 Cl2 O10 110.9(5) . . ? O13 Cl2 O10 109.3(4) . . ? O11 Cl2 O12 110.4(3) . . ? O13 Cl2 O12 109.1(3) . . ? O10 Cl2 O12 108.4(3) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.916 _refine_diff_density_min -1.458 _refine_diff_density_rms 0.137 # Attachment 'YK06-33.cif' data_yk0633 _database_code_depnum_ccdc_archive 'CCDC 678923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 N O6 S2' _chemical_formula_weight 447.51 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 15.361(3) _cell_length_b 5.9990(12) _cell_length_c 22.999(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2119.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7893 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 30.26 _exptl_crystal_description irregular _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'Synchrotron Radiation' _diffrn_radiation_source 'Sybchrotron Radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7385 _diffrn_reflns_av_R_equivalents 0.0585 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 30.26 _reflns_number_total 4351 _reflns_number_gt 3650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _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^)+(0.0921P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(8) _refine_ls_number_reflns 4351 _refine_ls_number_parameters 272 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.60706(5) 0.06480(12) 0.26590(4) 0.0436(2) Uani 1 1 d . . . S2 S 0.33142(5) 0.20754(13) 0.43511(3) 0.0458(2) Uani 1 1 d . . . O1 O 0.66851(15) 0.2004(5) 0.29533(13) 0.0613(7) Uani 1 1 d . . . O2 O 0.61002(17) -0.1708(4) 0.27312(13) 0.0612(7) Uani 1 1 d . . . O3 O 0.51297(13) 0.1328(3) 0.28549(9) 0.0408(5) Uani 1 1 d . . . O4 O 0.36652(16) 0.3419(4) 0.38171(10) 0.0489(5) Uani 1 1 d . . . O5 O 0.37211(19) 0.3149(5) 0.48310(10) 0.0664(7) Uani 1 1 d . . . O6 O 0.34298(17) -0.0259(4) 0.42536(12) 0.0607(7) Uani 1 1 d . . . N1 N 0.3269(2) 0.1685(6) 0.20226(16) 0.0674(9) Uani 1 1 d . . . C1 C 0.6482(2) 0.3282(6) 0.17277(18) 0.0553(8) Uani 1 1 d . . . H1 H 0.6717 0.4290 0.1992 0.066 Uiso 1 1 calc R . . C2 C 0.6505(3) 0.3696(8) 0.1133(2) 0.0740(12) Uani 1 1 d . . . H2 H 0.6758 0.4998 0.0994 0.089 Uiso 1 1 calc R . . C3 C 0.6155(3) 0.2195(9) 0.07538(19) 0.0801(14) Uani 1 1 d . . . H3 H 0.6175 0.2500 0.0358 0.096 Uiso 1 1 calc R . . C4 C 0.5777(3) 0.0255(8) 0.09374(19) 0.0771(12) Uani 1 1 d . . . H4 H 0.5550 -0.0747 0.0669 0.092 Uiso 1 1 calc R . . C5 C 0.5733(3) -0.0205(7) 0.15304(17) 0.0611(9) Uani 1 1 d . . . H5 H 0.5466 -0.1499 0.1664 0.073 Uiso 1 1 calc R . . C6 C 0.6093(2) 0.1292(5) 0.19152(15) 0.0471(7) Uani 1 1 d . . . C7 C 0.49465(19) 0.3712(4) 0.29210(14) 0.0400(6) Uani 1 1 d . . . H7A H 0.5289 0.4565 0.2645 0.048 Uiso 1 1 calc R . . H7B H 0.5098 0.4198 0.3310 0.048 Uiso 1 1 calc R . . C8 C 0.39773(18) 0.4087(4) 0.28112(12) 0.0377(7) Uani 1 1 d . . . C9 C 0.3811(2) 0.6584(5) 0.29134(19) 0.0535(8) Uani 1 1 d . . . H9A H 0.3943 0.6950 0.3310 0.080 Uiso 1 1 calc R . . H9B H 0.3211 0.6916 0.2835 0.080 Uiso 1 1 calc R . . H9C H 0.4175 0.7444 0.2659 0.080 Uiso 1 1 calc R . . C10 C 0.3774(2) 0.3473(5) 0.21791(14) 0.0412(6) Uani 1 1 d . . . C11 C 0.4176(2) 0.4756(5) 0.17839(14) 0.0478(7) Uani 1 1 d . . . H11 H 0.4528 0.5940 0.1896 0.057 Uiso 1 1 calc R . . C12 C 0.4050(3) 0.4269(8) 0.12226(18) 0.0729(12) Uani 1 1 d . . . H12 H 0.4316 0.5175 0.0946 0.087 Uiso 1 1 calc R . . C13 C 0.3554(3) 0.2515(8) 0.10283(18) 0.0714(11) Uani 1 1 d . . . H13 H 0.3487 0.2238 0.0633 0.086 Uiso 1 1 calc R . . C14 C 0.3160(3) 0.1182(8) 0.14371(18) 0.0678(10) Uani 1 1 d . . . H14 H 0.2826 -0.0035 0.1324 0.081 Uiso 1 1 calc R . . C15 C 0.3425(2) 0.2709(5) 0.32218(14) 0.0428(6) Uani 1 1 d . . . H15A H 0.2811 0.2975 0.3151 0.051 Uiso 1 1 calc R . . H15B H 0.3542 0.1133 0.3169 0.051 Uiso 1 1 calc R . . C16 C 0.2195(2) 0.2664(5) 0.43634(15) 0.0449(6) Uani 1 1 d . . . C17 C 0.1922(3) 0.4726(6) 0.45527(18) 0.0644(10) Uani 1 1 d . . . H17 H 0.2322 0.5816 0.4660 0.077 Uiso 1 1 calc R . . C18 C 0.1031(3) 0.5134(9) 0.4580(2) 0.0815(14) Uani 1 1 d . . . H18 H 0.0829 0.6519 0.4701 0.098 Uiso 1 1 calc R . . C19 C 0.0448(3) 0.3493(8) 0.44259(19) 0.0748(12) Uani 1 1 d . . . H19 H -0.0146 0.3778 0.4447 0.090 Uiso 1 1 calc R . . C20 C 0.0731(3) 0.1454(8) 0.4243(2) 0.0769(12) Uani 1 1 d . . . H20 H 0.0331 0.0360 0.4139 0.092 Uiso 1 1 calc R . . C21 C 0.1617(2) 0.1018(7) 0.42123(17) 0.0589(9) Uani 1 1 d . . . H21 H 0.1816 -0.0370 0.4091 0.071 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 S1 0.0378(4) 0.0401(4) 0.0530(4) 0.0063(3) 0.0024(3) 0.0047(3) S2 0.0458(4) 0.0494(4) 0.0422(4) 0.0025(3) -0.0001(4) -0.0005(3) O1 0.0429(12) 0.0743(17) 0.0669(16) 0.0029(13) -0.0061(12) -0.0070(10) O2 0.0627(14) 0.0399(11) 0.0810(18) 0.0179(13) 0.0101(13) 0.0178(10) O3 0.0378(10) 0.0323(9) 0.0522(11) 0.0027(8) 0.0040(9) 0.0027(8) O4 0.0518(12) 0.0523(12) 0.0425(11) -0.0046(10) 0.0061(10) -0.0122(10) O5 0.0692(18) 0.0881(19) 0.0419(13) -0.0038(13) -0.0080(13) -0.0137(15) O6 0.0656(15) 0.0506(13) 0.0659(16) 0.0060(12) 0.0054(12) 0.0131(11) N1 0.062(2) 0.076(2) 0.0640(19) -0.0001(16) -0.0005(16) -0.0120(16) C1 0.0522(19) 0.0490(19) 0.065(2) 0.0073(15) 0.0067(17) 0.0030(16) C2 0.075(3) 0.075(3) 0.072(3) 0.028(2) 0.020(2) 0.006(2) C3 0.082(3) 0.105(4) 0.053(2) 0.015(3) 0.016(2) 0.014(3) C4 0.088(3) 0.081(3) 0.062(2) -0.014(2) 0.001(2) 0.007(2) C5 0.067(2) 0.0502(19) 0.066(2) -0.0056(16) 0.0045(18) -0.0017(18) C6 0.0461(17) 0.0403(15) 0.0547(17) -0.0015(14) 0.0076(14) 0.0050(13) C7 0.0402(14) 0.0314(13) 0.0483(14) -0.0046(11) 0.0034(13) -0.0005(11) C8 0.0390(15) 0.0312(13) 0.0429(16) 0.0022(10) 0.0035(11) 0.0029(10) C9 0.0537(18) 0.0355(14) 0.071(2) -0.0002(15) 0.0045(18) 0.0066(14) C10 0.0391(14) 0.0385(15) 0.0460(15) 0.0039(12) 0.0020(12) 0.0038(12) C11 0.0600(19) 0.0437(15) 0.0396(14) 0.0096(13) 0.0033(14) -0.0142(15) C12 0.088(3) 0.078(3) 0.052(2) 0.0201(19) 0.001(2) -0.014(2) C13 0.074(3) 0.093(3) 0.0469(19) 0.0041(19) -0.0061(19) -0.009(2) C14 0.066(2) 0.079(3) 0.058(2) -0.0055(19) -0.0068(19) -0.020(2) C15 0.0425(15) 0.0435(15) 0.0422(15) -0.0013(13) 0.0039(13) -0.0070(12) C16 0.0495(15) 0.0447(15) 0.0405(12) 0.0051(13) 0.0087(15) 0.0013(12) C17 0.071(2) 0.0506(19) 0.072(2) 0.0065(17) 0.013(2) 0.0081(18) C18 0.089(3) 0.075(3) 0.080(3) 0.021(2) 0.025(2) 0.042(3) C19 0.058(2) 0.093(3) 0.074(2) 0.030(2) 0.013(2) 0.017(2) C20 0.050(2) 0.103(3) 0.078(3) 0.018(3) -0.006(2) -0.010(2) C21 0.0540(19) 0.062(2) 0.061(2) -0.0020(16) 0.0018(16) -0.0033(16) _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 S1 O1 1.418(3) . ? S1 O2 1.424(2) . ? S1 O3 1.568(2) . ? S1 C6 1.754(4) . ? S2 O5 1.423(3) . ? S2 O6 1.430(3) . ? S2 O4 1.565(2) . ? S2 C16 1.755(3) . ? O3 C7 1.466(3) . ? O4 C15 1.481(4) . ? N1 C10 1.371(5) . ? N1 C14 1.390(6) . ? C1 C2 1.390(6) . ? C1 C6 1.403(5) . ? C2 C3 1.364(7) . ? C3 C4 1.368(7) . ? C4 C5 1.393(6) . ? C5 C6 1.377(5) . ? C7 C8 1.527(4) . ? C8 C15 1.515(4) . ? C8 C10 1.532(4) . ? C8 C9 1.537(4) . ? C10 C11 1.341(4) . ? C11 C12 1.337(6) . ? C12 C13 1.374(6) . ? C13 C14 1.374(6) . ? C16 C21 1.373(5) . ? C16 C17 1.377(5) . ? C17 C18 1.392(7) . ? C18 C19 1.376(7) . ? C19 C20 1.365(7) . ? C20 C21 1.387(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 119.51(16) . . ? O1 S1 O3 109.10(14) . . ? O2 S1 O3 104.73(13) . . ? O1 S1 C6 109.02(17) . . ? O2 S1 C6 109.37(16) . . ? O3 S1 C6 103.95(13) . . ? O5 S2 O6 120.72(18) . . ? O5 S2 O4 102.96(14) . . ? O6 S2 O4 109.79(14) . . ? O5 S2 C16 109.07(17) . . ? O6 S2 C16 108.75(15) . . ? O4 S2 C16 104.27(14) . . ? C7 O3 S1 117.44(17) . . ? C15 O4 S2 119.46(18) . . ? C10 N1 C14 119.5(3) . . ? C2 C1 C6 117.7(4) . . ? C3 C2 C1 120.1(4) . . ? C2 C3 C4 122.1(4) . . ? C3 C4 C5 119.4(4) . . ? C6 C5 C4 118.7(4) . . ? C5 C6 C1 121.9(4) . . ? C5 C6 S1 118.4(3) . . ? C1 C6 S1 119.7(3) . . ? O3 C7 C8 108.3(2) . . ? C15 C8 C7 111.3(2) . . ? C15 C8 C10 110.2(2) . . ? C7 C8 C10 108.7(2) . . ? C15 C8 C9 110.1(3) . . ? C7 C8 C9 106.3(2) . . ? C10 C8 C9 110.2(2) . . ? C11 C10 N1 122.1(3) . . ? C11 C10 C8 114.3(3) . . ? N1 C10 C8 123.5(3) . . ? C12 C11 C10 117.6(3) . . ? C11 C12 C13 124.1(4) . . ? C12 C13 C14 117.9(4) . . ? C13 C14 N1 118.9(4) . . ? O4 C15 C8 106.3(2) . . ? C21 C16 C17 121.9(3) . . ? C21 C16 S2 119.0(2) . . ? C17 C16 S2 119.0(3) . . ? C16 C17 C18 118.2(4) . . ? C19 C18 C17 120.1(4) . . ? C20 C19 C18 120.9(4) . . ? C19 C20 C21 119.8(4) . . ? C16 C21 C20 119.1(4) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.476 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.088 # Attachment 'YK06-44.cif' data_yk0644 _database_code_depnum_ccdc_archive 'CCDC 678924' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 Cl2 Cu N3 O' _chemical_formula_weight 343.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.943(5) _cell_length_b 8.1320(16) _cell_length_c 17.501(4) _cell_angle_alpha 90.00 _cell_angle_beta 126.79(3) _cell_angle_gamma 90.00 _cell_volume 2956.8(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6286 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 30.41 _exptl_crystal_description irregular _exptl_crystal_colour 'Dark Green' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 1.831 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.76999 _diffrn_radiation_type 'Synchrotron Radiation' _diffrn_radiation_source 'Synchrotron Radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6079 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 30.41 _reflns_number_total 3378 _reflns_number_gt 2976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _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^)+(0.1042P)^2^+1.6242P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0066(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3378 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1462 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.102721(14) 0.94012(4) 0.47567(2) 0.04215(19) Uani 1 1 d . . . Cl1 Cl 0.09163(4) 1.17451(10) 0.54521(7) 0.0613(3) Uani 1 1 d . . . Cl2 Cl 0.10255(4) 1.01057(13) 0.34231(5) 0.0589(3) Uani 1 1 d . . . N1 N 0.20126(11) 0.9499(2) 0.56683(17) 0.0387(5) Uani 1 1 d . . . N2 N 0.10859(10) 0.7047(3) 0.52037(16) 0.0392(5) Uani 1 1 d . . . N3 N 0.00793(12) 0.8924(4) 0.38735(19) 0.0531(6) Uani 1 1 d . . . H3A H -0.0115 0.9286 0.4129 0.064 Uiso 1 1 calc R . . H3B H -0.0100 0.9432 0.3310 0.064 Uiso 1 1 calc R . . C1 C 0.22721(14) 1.0930(3) 0.5684(2) 0.0453(6) Uani 1 1 d . . . H1 H 0.1997 1.1784 0.5306 0.054 Uiso 1 1 calc R . . C2 C 0.29287(13) 1.1208(4) 0.6233(2) 0.0455(6) Uani 1 1 d . . . H2 H 0.3092 1.2225 0.6232 0.055 Uiso 1 1 calc R . . C3 C 0.33292(13) 0.9935(4) 0.6778(2) 0.0473(6) Uani 1 1 d . . . H3 H 0.3773 1.0075 0.7151 0.057 Uiso 1 1 calc R . . C4 C 0.30715(12) 0.8436(4) 0.6772(2) 0.0470(6) Uani 1 1 d . . . H4 H 0.3342 0.7569 0.7143 0.056 Uiso 1 1 calc R . . C5 C 0.24077(11) 0.8236(3) 0.62119(17) 0.0352(5) Uani 1 1 d . . . C6 C 0.20984(12) 0.6641(3) 0.61817(18) 0.0395(5) Uani 1 1 d . . . C7 C 0.25773(17) 0.5307(4) 0.6828(3) 0.0618(9) Uani 1 1 d . . . H7A H 0.2349 0.4332 0.6772 0.093 Uiso 1 1 calc R . . H7B H 0.2836 0.5682 0.7477 0.093 Uiso 1 1 calc R . . H7C H 0.2850 0.5066 0.6641 0.093 Uiso 1 1 calc R . . C8 C 0.15424(14) 0.6924(4) 0.62614(19) 0.0443(6) Uani 1 1 d . . . H8A H 0.1461 0.5992 0.6522 0.053 Uiso 1 1 calc R . . H8B H 0.1583 0.7932 0.6590 0.053 Uiso 1 1 calc R . . C9 C 0.15577(13) 0.6126(3) 0.5132(2) 0.0443(6) Uani 1 1 d . . . H9A H 0.1609 0.6580 0.4669 0.053 Uiso 1 1 calc R . . H9B H 0.1481 0.4950 0.5045 0.053 Uiso 1 1 calc R . . C10 C 0.04312(15) 0.6381(4) 0.4723(3) 0.0550(7) Uani 1 1 d . . . H10A H 0.0270 0.6648 0.5085 0.066 Uiso 1 1 calc R . . H10B H 0.0436 0.5194 0.4672 0.066 Uiso 1 1 calc R . . C11 C 0.00052(14) 0.7143(4) 0.3739(2) 0.0607(8) Uani 1 1 d . . . H11A H 0.0136 0.6779 0.3350 0.073 Uiso 1 1 calc R . . H11B H -0.0440 0.6830 0.3424 0.073 Uiso 1 1 calc R . . O1 O 0.46815(14) 1.2016(4) 0.8240(2) 0.280(6) Uani 1 1 d R . . H1A' H 0.4514 1.3108 0.7961 0.336 Uiso 1 1 calc R . . H1A" H 0.4963 1.2730 0.8736 0.336 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 Cu1 0.0252(2) 0.0445(3) 0.0451(3) 0.00853(12) 0.01488(18) -0.00013(10) Cl1 0.0482(4) 0.0603(5) 0.0793(6) -0.0096(4) 0.0402(4) 0.0034(3) Cl2 0.0415(4) 0.0893(6) 0.0400(4) 0.0020(3) 0.0213(3) -0.0129(4) N1 0.0261(10) 0.0393(11) 0.0418(11) 0.0034(8) 0.0156(9) -0.0002(7) N2 0.0320(10) 0.0389(10) 0.0464(11) -0.0003(8) 0.0233(9) -0.0038(8) N3 0.0279(11) 0.0732(16) 0.0461(13) 0.0088(12) 0.0156(10) -0.0024(11) C1 0.0356(13) 0.0404(12) 0.0513(15) 0.0067(11) 0.0215(12) -0.0014(10) C2 0.0380(13) 0.0468(14) 0.0498(15) -0.0072(11) 0.0253(12) -0.0097(11) C3 0.0292(12) 0.0556(15) 0.0508(15) -0.0060(13) 0.0206(11) -0.0044(11) C4 0.0296(12) 0.0529(15) 0.0478(14) 0.0037(12) 0.0173(11) 0.0061(10) C5 0.0293(11) 0.0397(11) 0.0340(11) 0.0008(9) 0.0175(9) 0.0031(9) C6 0.0343(12) 0.0395(12) 0.0428(13) 0.0049(10) 0.0222(10) 0.0041(9) C7 0.0500(18) 0.0480(15) 0.075(2) 0.0183(15) 0.0313(17) 0.0111(13) C8 0.0444(14) 0.0491(14) 0.0435(13) 0.0061(11) 0.0285(12) 0.0012(11) C9 0.0407(14) 0.0413(12) 0.0532(15) -0.0072(11) 0.0293(12) -0.0031(10) C10 0.0391(15) 0.0520(15) 0.0710(19) -0.0039(14) 0.0315(14) -0.0120(12) C11 0.0363(14) 0.080(2) 0.0532(16) -0.0159(15) 0.0197(13) -0.0138(14) O1 0.224(8) 0.157(5) 0.181(6) 0.062(5) -0.027(5) -0.105(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 Cu1 N3 2.009(3) . ? Cu1 N2 2.039(2) . ? Cu1 N1 2.050(2) . ? Cu1 Cl1 2.3699(9) . ? Cu1 Cl2 2.4005(9) . ? N1 C1 1.337(3) . ? N1 C5 1.357(3) . ? N2 C10 1.475(3) . ? N2 C8 1.488(4) . ? N2 C9 1.503(3) . ? N3 C11 1.461(4) . ? C1 C2 1.384(4) . ? C2 C3 1.369(4) . ? C3 C4 1.388(4) . ? C4 C5 1.390(3) . ? C5 C6 1.510(3) . ? C6 C7 1.522(4) . ? C6 C8 1.547(4) . ? C6 C9 1.559(4) . ? C10 C11 1.514(5) . ? 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 N3 Cu1 N2 83.65(10) . . ? N3 Cu1 N1 171.06(10) . . ? N2 Cu1 N1 88.04(8) . . ? N3 Cu1 Cl1 94.67(9) . . ? N2 Cu1 Cl1 124.21(7) . . ? N1 Cu1 Cl1 92.73(7) . . ? N3 Cu1 Cl2 90.54(9) . . ? N2 Cu1 Cl2 123.60(7) . . ? N1 Cu1 Cl2 91.31(8) . . ? Cl1 Cu1 Cl2 112.16(4) . . ? C1 N1 C5 119.0(2) . . ? C1 N1 Cu1 115.32(18) . . ? C5 N1 Cu1 125.65(17) . . ? C10 N2 C8 118.2(2) . . ? C10 N2 C9 119.1(2) . . ? C8 N2 C9 89.3(2) . . ? C10 N2 Cu1 109.28(18) . . ? C8 N2 Cu1 111.21(16) . . ? C9 N2 Cu1 108.28(16) . . ? C11 N3 Cu1 107.34(19) . . ? N1 C1 C2 123.5(3) . . ? C3 C2 C1 117.7(3) . . ? C2 C3 C4 119.9(3) . . ? C3 C4 C5 119.7(2) . . ? N1 C5 C4 120.2(2) . . ? N1 C5 C6 117.6(2) . . ? C4 C5 C6 122.2(2) . . ? C5 C6 C7 114.0(2) . . ? C5 C6 C8 112.0(2) . . ? C7 C6 C8 115.4(2) . . ? C5 C6 C9 110.9(2) . . ? C7 C6 C9 116.2(2) . . ? C8 C6 C9 85.21(19) . . ? N2 C8 C6 89.33(19) . . ? N2 C9 C6 88.34(19) . . ? N2 C10 C11 107.8(2) . . ? N3 C11 C10 106.6(2) . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.582 _refine_diff_density_min -0.911 _refine_diff_density_rms 0.126 # Attachment 'YK06-62.cif' data_yk0662 _database_code_depnum_ccdc_archive 'CCDC 678925' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H40 Cl2 N8 Ni2 O4' _chemical_formula_weight 692.96 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P1 21/n 1' 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 8.5520(17) _cell_length_b 7.9080(16) _cell_length_c 21.228(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.18(3) _cell_angle_gamma 90.00 _cell_volume 1435.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5406 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 30.38 _exptl_crystal_description irregular _exptl_crystal_colour 'Dark Yellow' _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.603 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.544 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details 'crystal-to-detector distance 60 mm' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.80000 _diffrn_radiation_type 'Synchrotron Radiation' _diffrn_radiation_source 'Synchrotron Radiation' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'ADSC Quantum 210' _diffrn_measurement_method 'two \f and two \w scans with 2\% steps' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5186 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 30.38 _reflns_number_total 2834 _reflns_number_gt 2736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _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^)+(0.0692P)^2^+1.3864P] 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 SHELXL _refine_ls_extinction_coef 0.0143(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2834 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.37021(3) 0.26694(4) 0.050461(12) 0.00762(16) Uani 1 1 d . . . Cl1 Cl 0.83911(7) -0.25767(7) 0.16799(3) 0.01482(18) Uani 1 1 d . . . N1 N 0.2563(2) 0.4727(2) 0.02904(8) 0.0096(4) Uani 1 1 d . . . N2 N 0.5045(2) 0.0927(2) 0.07376(8) 0.0099(4) Uani 1 1 d . . . N3 N 0.3936(2) 0.3379(2) 0.13615(8) 0.0084(4) Uani 1 1 d . . . N4 N 0.3683(2) 0.1531(3) -0.02949(8) 0.0118(4) Uani 1 1 d . . . C1 C 0.1269(2) 0.6333(3) -0.05225(10) 0.0141(5) Uani 1 1 d . . . C2 C 0.5408(2) -0.0182(3) 0.03019(9) 0.0100(4) Uani 1 1 d . . . C3 C 0.4796(2) 0.5036(3) 0.13386(10) 0.0115(4) Uani 1 1 d . . . C5 C 0.4565(3) 0.1973(3) 0.17566(10) 0.0115(4) Uani 1 1 d . . . C6 C 0.3181(2) 0.5944(3) 0.13297(9) 0.0089(4) Uani 1 1 d . . . C7 C 0.1898(2) 0.4848(3) -0.02895(10) 0.0123(5) Uani 1 1 d . . . C8 C 0.2537(2) 0.6124(3) 0.06658(10) 0.0094(4) Uani 1 1 d . . . C9 C 0.2557(2) 0.4292(3) 0.16263(10) 0.0103(4) Uani 1 1 d . . . C10 C 0.1271(3) 0.7745(3) -0.01494(12) 0.0164(5) Uani 1 1 d . . . C11 C 0.1890(3) 0.7639(3) 0.04545(12) 0.0140(5) Uani 1 1 d . . . C12 C 0.5750(3) 0.1025(3) 0.13646(9) 0.0115(4) Uani 1 1 d . . . C13 C 0.3046(3) 0.7526(3) 0.17259(13) 0.0168(5) Uani 1 1 d . . . O1 O 0.8692(3) 0.3593(3) 0.21641(10) 0.0278(5) Uani 1 1 d . . . O2 O 1.0413(3) 0.0849(3) 0.16782(14) 0.0419(6) Uani 1 1 d . . . H1 H 0.155(3) 0.387(4) 0.1490(13) 0.012(6) Uiso 1 1 d . . . H2 H 0.601(3) 0.001(4) 0.1527(12) 0.007(6) Uiso 1 1 d . . . H3 H 0.190(3) 0.858(4) 0.0731(14) 0.016(7) Uiso 1 1 d . . . H4 H 0.351(4) 0.731(4) 0.2132(18) 0.013(9) Uiso 1 1 d . . . H5 H 0.184(3) 0.387(4) -0.0539(12) 0.007(6) Uiso 1 1 d . . . H6 H 0.547(3) 0.521(4) 0.0971(13) 0.012(7) Uiso 1 1 d . . . H7 H 0.361(3) 0.132(4) 0.1811(14) 0.018(7) Uiso 1 1 d . . . H8 H 0.085(3) 0.870(4) -0.0297(13) 0.010(6) Uiso 1 1 d . . . H9 H 0.531(3) 0.522(4) 0.1762(14) 0.011(7) Uiso 1 1 d . . . H10 H 0.317(5) 0.161(5) -0.0650(18) 0.021(10) Uiso 1 1 d . . . H11 H 0.677(3) 0.164(4) 0.1342(13) 0.016(7) Uiso 1 1 d . . . H12 H 0.265(3) 0.437(4) 0.2087(13) 0.015(7) Uiso 1 1 d . . . H13 H 0.359(4) 0.849(4) 0.1534(15) 0.012(7) Uiso 1 1 d . . . H14 H 0.495(4) 0.244(4) 0.2141(17) 0.019(8) Uiso 1 1 d . . . H15 H 0.084(4) 0.637(4) -0.0928(15) 0.012(8) Uiso 1 1 d . . . H16 H 0.980(5) 0.157(6) 0.1882(19) 0.014(11) Uiso 1 1 d . . . H17 H 0.201(5) 0.788(5) 0.1792(18) 0.019(10) Uiso 1 1 d . . . H18 H 0.815(5) 0.342(6) 0.246(2) 0.017(11) Uiso 1 1 d . . . H19 H 0.985(8) 0.005(9) 0.176(3) 0.010(2) Uiso 1 1 d . . . H20 H 0.858(4) 0.452(6) 0.2073(17) 0.011(10) Uiso 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 Ni1 0.0103(2) 0.0072(2) 0.0054(2) -0.00097(9) -0.00100(12) 0.00190(9) Cl1 0.0185(3) 0.0142(4) 0.0117(3) -0.00189(17) -0.0036(2) 0.00018(18) N1 0.0086(8) 0.0124(10) 0.0077(8) -0.0006(7) 0.0014(6) 0.0016(7) N2 0.0129(8) 0.0098(10) 0.0070(8) -0.0020(6) -0.0030(6) 0.0022(7) N3 0.0117(8) 0.0043(10) 0.0090(8) 0.0003(7) 0.0003(6) -0.0005(7) N4 0.0145(9) 0.0121(10) 0.0088(8) -0.0009(7) -0.0025(6) 0.0056(7) C1 0.0138(11) 0.0168(14) 0.0116(10) 0.0031(8) -0.0003(8) 0.0017(8) C2 0.0106(9) 0.0125(12) 0.0068(9) 0.0004(8) -0.0011(7) -0.0018(8) C3 0.0105(9) 0.0108(12) 0.0131(10) -0.0025(8) 0.0001(7) -0.0034(8) C5 0.0177(11) 0.0082(11) 0.0087(10) -0.0005(8) -0.0020(8) 0.0033(9) C6 0.0118(9) 0.0030(11) 0.0119(10) -0.0017(8) 0.0008(7) -0.0010(7) C7 0.0117(10) 0.0176(13) 0.0076(9) -0.0013(8) 0.0015(7) 0.0014(8) C8 0.0097(9) 0.0069(12) 0.0115(9) 0.0004(8) 0.0021(7) -0.0021(7) C9 0.0104(10) 0.0105(12) 0.0099(10) -0.0008(8) 0.0024(7) 0.0003(8) C10 0.0174(12) 0.0143(14) 0.0174(12) 0.0058(9) 0.0014(9) 0.0055(9) C11 0.0149(12) 0.0127(13) 0.0144(11) -0.0017(8) 0.0001(9) 0.0017(8) C12 0.0167(10) 0.0105(12) 0.0072(9) -0.0006(8) -0.0041(8) 0.0036(9) C13 0.0206(13) 0.0137(14) 0.0161(12) -0.0062(8) -0.0030(10) 0.0022(9) O1 0.0414(12) 0.0174(13) 0.0245(10) 0.0035(8) 0.0119(8) 0.0044(9) O2 0.0229(11) 0.0200(13) 0.0829(19) -0.0061(12) 0.0089(11) -0.0005(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N2 1.8600(19) . ? Ni1 N3 1.9134(17) . ? Ni1 N4 1.9211(19) . ? Ni1 N1 1.9496(19) . ? N1 C7 1.358(3) . ? N1 C8 1.362(3) . ? N2 C2 1.312(3) . ? N2 C12 1.461(3) . ? N3 C5 1.492(3) . ? N3 C9 1.494(3) . ? N3 C3 1.504(3) . ? N4 C2 1.321(3) 3_655 ? C1 C10 1.370(4) . ? C1 C7 1.383(3) . ? C2 N4 1.321(3) 3_655 ? C2 C2 1.485(4) 3_655 ? C3 C6 1.557(3) . ? C5 C12 1.512(3) . ? C6 C13 1.512(3) . ? C6 C8 1.518(3) . ? C6 C9 1.546(3) . ? C8 C11 1.394(3) . ? C10 C11 1.388(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N3 84.37(8) . . ? N2 Ni1 N4 83.76(8) . . ? N3 Ni1 N4 167.90(8) . . ? N2 Ni1 N1 171.16(8) . . ? N3 Ni1 N1 91.59(8) . . ? N4 Ni1 N1 100.50(8) . . ? C7 N1 C8 117.77(19) . . ? C7 N1 Ni1 118.53(15) . . ? C8 N1 Ni1 123.33(14) . . ? C2 N2 C12 125.43(18) . . ? C2 N2 Ni1 117.05(14) . . ? C12 N2 Ni1 117.09(14) . . ? C5 N3 C9 115.62(16) . . ? C5 N3 C3 119.47(17) . . ? C9 N3 C3 88.71(16) . . ? C5 N3 Ni1 110.64(13) . . ? C9 N3 Ni1 114.78(13) . . ? C3 N3 Ni1 105.92(12) . . ? C2 N4 Ni1 112.65(14) 3_655 . ? C10 C1 C7 119.1(2) . . ? N2 C2 N4 133.50(19) . 3_655 ? N2 C2 C2 111.6(2) . 3_655 ? N4 C2 C2 114.9(2) 3_655 3_655 ? N3 C3 C6 88.17(15) . . ? N3 C5 C12 107.52(17) . . ? C13 C6 C8 114.23(19) . . ? C13 C6 C9 116.45(19) . . ? C8 C6 C9 109.42(17) . . ? C13 C6 C3 116.38(19) . . ? C8 C6 C3 111.95(17) . . ? C9 C6 C3 85.01(16) . . ? N1 C7 C1 123.1(2) . . ? N1 C8 C11 121.07(19) . . ? N1 C8 C6 117.42(19) . . ? C11 C8 C6 121.5(2) . . ? N3 C9 C6 88.94(15) . . ? C1 C10 C11 119.0(2) . . ? C10 C11 C8 119.9(2) . . ? N2 C12 C5 104.61(17) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 28.68 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.773 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.108