# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Armando J L Pombeiro' "Maria de F\'atima Guedes da Silva" 'Luisa M D R S Martins' 'Gopal S. Mishra' 'Telma F. S. Silva' 'Riccardo Wanke' _publ_contact_author_name 'Armando J L Pombeiro' _publ_contact_author_email POMBEIRO@IST.UTL.PT _publ_section_title ; Water-soluble CuII complexes bearing the 2,2,2-tris(1-pyrazolyl)ethanol or 2,2,2-tris(1-pyrazolyl)ethyl methanesulfonate scorpionates. X-ray structural characterization and application in the mild catalytic peroxidative oxidation of cyclohexane ; # Attachment 'cifs.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 736870' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N6 O3 S' _chemical_formula_sum 'C12 H14 N6 O3 S' _chemical_formula_weight 322.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_space_group_name_Hall '-P 2yn' 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 7.7397(16) _cell_length_b 12.757(3) _cell_length_c 14.957(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.719(12) _cell_angle_gamma 90.00 _cell_volume 1434.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9527 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 29.34 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9655 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35129 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 29.34 _reflns_number_total 3941 _reflns_number_gt 3220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0469P)^2^+0.5257P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3941 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.22460(16) 0.96617(10) 0.26954(8) 0.0175(2) Uani 1 1 d . . . C2 C 0.10913(16) 1.01269(10) 0.18030(9) 0.0180(2) Uani 1 1 d . . . C3 C -0.33449(18) 1.01017(13) 0.14872(11) 0.0267(3) Uani 1 1 d . . . C13 C 0.38130(19) 1.07276(12) 0.40885(9) 0.0262(3) Uani 1 1 d . . . C12 C 0.5041(2) 1.15121(12) 0.42073(11) 0.0310(3) Uani 1 1 d . . . C11 C 0.52633(18) 1.17181(11) 0.33253(11) 0.0287(3) Uani 1 1 d . . . C16 C 0.32822(17) 0.82587(10) 0.17378(10) 0.0216(3) Uani 1 1 d . . . C15 C 0.46660(18) 0.75628(11) 0.19304(11) 0.0273(3) Uani 1 1 d . . . C14 C 0.55429(18) 0.77636(11) 0.28459(11) 0.0300(3) Uani 1 1 d . . . C19 C 0.11902(19) 0.83355(11) 0.37206(10) 0.0266(3) Uani 1 1 d . . . C18 C -0.0122(2) 0.83725(13) 0.41833(10) 0.0333(3) Uani 1 1 d . . . C17 C -0.0921(2) 0.93558(13) 0.39796(10) 0.0307(3) Uani 1 1 d . . . N13 N 0.33458(14) 1.05106(9) 0.31770(7) 0.0191(2) Uani 1 1 d . . . N11 N 0.42451(15) 1.11110(9) 0.26906(8) 0.0247(2) Uani 1 1 d . . . N16 N 0.33949(14) 0.88278(8) 0.25162(7) 0.0200(2) Uani 1 1 d . . . N14 N 0.47876(16) 0.85298(10) 0.32141(9) 0.0281(3) Uani 1 1 d . . . N19 N 0.11355(14) 0.92673(9) 0.32745(7) 0.0210(2) Uani 1 1 d . . . N17 N -0.01706(16) 0.99108(10) 0.34271(8) 0.0259(3) Uani 1 1 d . . . O1 O -0.02409(11) 0.93555(7) 0.13941(6) 0.02022(19) Uani 1 1 d . . . O2 O -0.27556(14) 0.89193(10) 0.01750(8) 0.0397(3) Uani 1 1 d . . . O3 O -0.16165(14) 1.07290(9) 0.03048(7) 0.0324(3) Uani 1 1 d . . . S1 S -0.20190(4) 0.97904(3) 0.07315(2) 0.02247(10) Uani 1 1 d . . . H2A H 0.178(2) 1.0289(13) 0.1378(12) 0.027 Uiso 1 1 d . . . H2B H 0.054(2) 1.0752(13) 0.1964(12) 0.027 Uiso 1 1 d . . . H3A H -0.267(2) 1.0598(13) 0.1938(12) 0.027 Uiso 1 1 d . . . H3B H -0.442(2) 1.0430(13) 0.1122(12) 0.027 Uiso 1 1 d . . . H3C H -0.358(2) 0.9468(13) 0.1768(12) 0.027 Uiso 1 1 d . . . H13 H 0.333(2) 1.0362(13) 0.4494(12) 0.027 Uiso 1 1 d . . . H12 H 0.553(2) 1.1834(13) 0.4742(12) 0.027 Uiso 1 1 d . . . H11 H 0.601(2) 1.2204(13) 0.3148(11) 0.027 Uiso 1 1 d . . . H16 H 0.238(2) 0.8372(13) 0.1213(11) 0.027 Uiso 1 1 d . . . H15 H 0.494(2) 0.7047(14) 0.1550(11) 0.027 Uiso 1 1 d . . . H14 H 0.655(2) 0.7445(13) 0.3212(11) 0.027 Uiso 1 1 d . . . H19 H 0.198(2) 0.7819(13) 0.3678(11) 0.027 Uiso 1 1 d . . . H18 H -0.038(2) 0.7863(13) 0.4555(12) 0.027 Uiso 1 1 d . . . H17 H -0.196(2) 0.9643(13) 0.4144(12) 0.027 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 C1 0.0170(5) 0.0173(6) 0.0178(6) 0.0005(4) 0.0035(4) 0.0000(4) C2 0.0167(5) 0.0180(6) 0.0184(6) 0.0007(5) 0.0022(4) 0.0001(4) C3 0.0192(6) 0.0326(8) 0.0302(7) 0.0005(6) 0.0099(5) 0.0002(5) C13 0.0289(7) 0.0283(7) 0.0185(6) 0.0011(5) -0.0003(5) 0.0017(5) C12 0.0283(7) 0.0294(8) 0.0289(7) -0.0058(6) -0.0061(6) 0.0004(6) C11 0.0209(6) 0.0240(7) 0.0405(8) -0.0052(6) 0.0060(6) -0.0038(5) C16 0.0205(6) 0.0198(6) 0.0252(6) -0.0009(5) 0.0070(5) -0.0018(5) C15 0.0238(6) 0.0191(6) 0.0409(8) -0.0022(6) 0.0115(6) 0.0007(5) C14 0.0207(6) 0.0199(7) 0.0461(9) 0.0024(6) 0.0012(6) 0.0033(5) C19 0.0293(7) 0.0240(7) 0.0234(6) 0.0039(5) 0.0000(5) -0.0064(5) C18 0.0374(8) 0.0389(9) 0.0235(7) 0.0049(6) 0.0071(6) -0.0148(7) C17 0.0280(7) 0.0428(9) 0.0237(7) -0.0038(6) 0.0108(6) -0.0094(6) N13 0.0180(5) 0.0200(5) 0.0188(5) -0.0007(4) 0.0034(4) -0.0010(4) N11 0.0237(5) 0.0236(6) 0.0295(6) -0.0014(5) 0.0117(5) -0.0044(4) N16 0.0179(5) 0.0185(5) 0.0222(5) 0.0006(4) 0.0023(4) 0.0025(4) N14 0.0229(5) 0.0249(6) 0.0312(6) 0.0013(5) -0.0043(5) 0.0051(5) N19 0.0210(5) 0.0226(6) 0.0197(5) 0.0022(4) 0.0056(4) -0.0009(4) N17 0.0238(5) 0.0308(6) 0.0255(6) -0.0006(5) 0.0108(5) 0.0007(5) O1 0.0161(4) 0.0211(5) 0.0215(4) -0.0014(4) 0.0005(3) 0.0003(3) O2 0.0282(5) 0.0464(7) 0.0376(6) -0.0186(5) -0.0062(5) 0.0015(5) O3 0.0273(5) 0.0439(7) 0.0259(5) 0.0138(5) 0.0058(4) 0.0065(4) S1 0.01686(15) 0.03032(19) 0.01864(16) -0.00139(13) 0.00104(11) 0.00220(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N19 1.4475(16) . ? C1 N16 1.4516(16) . ? C1 N13 1.4579(16) . ? C1 C2 1.5385(17) . ? C2 O1 1.4514(15) . ? C2 H2A 0.942(18) . ? C2 H2B 0.963(17) . ? C3 S1 1.7432(15) . ? C3 H3A 0.980(18) . ? C3 H3B 0.973(18) . ? C3 H3C 0.949(17) . ? C13 N13 1.3535(17) . ? C13 C12 1.362(2) . ? C13 H13 0.913(17) . ? C12 C11 1.395(2) . ? C12 H12 0.900(17) . ? C11 N11 1.3293(18) . ? C11 H11 0.927(17) . ? C16 N16 1.3571(17) . ? C16 C15 1.3682(19) . ? C16 H16 0.929(17) . ? C15 C14 1.400(2) . ? C15 H15 0.925(17) . ? C14 N14 1.3240(19) . ? C14 H14 0.934(17) . ? C19 N19 1.3588(17) . ? C19 C18 1.359(2) . ? C19 H19 0.910(17) . ? C18 C17 1.400(2) . ? C18 H18 0.908(17) . ? C17 N17 1.3229(19) . ? C17 H17 0.965(17) . ? N13 N11 1.3567(15) . ? N16 N14 1.3647(15) . ? N19 N17 1.3629(16) . ? O1 S1 1.5928(10) . ? O2 S1 1.4240(12) . ? O3 S1 1.4255(12) . ? 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 N19 C1 N16 109.42(10) . . ? N19 C1 N13 108.81(10) . . ? N16 C1 N13 108.92(10) . . ? N19 C1 C2 110.37(10) . . ? N16 C1 C2 112.19(10) . . ? N13 C1 C2 107.04(10) . . ? O1 C2 C1 108.21(10) . . ? O1 C2 H2A 108.7(10) . . ? C1 C2 H2A 111.5(10) . . ? O1 C2 H2B 110.7(10) . . ? C1 C2 H2B 107.7(10) . . ? H2A C2 H2B 110.0(14) . . ? S1 C3 H3A 107.1(10) . . ? S1 C3 H3B 106.8(10) . . ? H3A C3 H3B 110.6(14) . . ? S1 C3 H3C 107.5(10) . . ? H3A C3 H3C 111.9(14) . . ? H3B C3 H3C 112.6(14) . . ? N13 C13 C12 107.04(13) . . ? N13 C13 H13 120.7(11) . . ? C12 C13 H13 132.2(11) . . ? C13 C12 C11 104.70(13) . . ? C13 C12 H12 125.9(11) . . ? C11 C12 H12 129.3(11) . . ? N11 C11 C12 112.35(13) . . ? N11 C11 H11 119.3(10) . . ? C12 C11 H11 128.3(10) . . ? N16 C16 C15 106.18(12) . . ? N16 C16 H16 121.5(10) . . ? C15 C16 H16 132.3(10) . . ? C16 C15 C14 105.12(13) . . ? C16 C15 H15 127.7(10) . . ? C14 C15 H15 127.1(10) . . ? N14 C14 C15 112.49(13) . . ? N14 C14 H14 117.9(10) . . ? C15 C14 H14 129.6(10) . . ? N19 C19 C18 106.24(14) . . ? N19 C19 H19 122.8(11) . . ? C18 C19 H19 130.9(11) . . ? C19 C18 C17 105.39(13) . . ? C19 C18 H18 126.0(11) . . ? C17 C18 H18 128.6(11) . . ? N17 C17 C18 112.25(14) . . ? N17 C17 H17 118.1(10) . . ? C18 C17 H17 129.5(10) . . ? C13 N13 N11 112.10(11) . . ? C13 N13 C1 129.40(11) . . ? N11 N13 C1 117.91(10) . . ? C11 N11 N13 103.80(11) . . ? C16 N16 N14 112.68(11) . . ? C16 N16 C1 129.27(11) . . ? N14 N16 C1 118.05(11) . . ? C14 N14 N16 103.54(12) . . ? C19 N19 N17 112.50(11) . . ? C19 N19 C1 130.09(12) . . ? N17 N19 C1 117.39(10) . . ? C17 N17 N19 103.61(12) . . ? C2 O1 S1 116.65(8) . . ? O2 S1 O3 119.57(8) . . ? O2 S1 O1 105.00(6) . . ? O3 S1 O1 108.83(6) . . ? O2 S1 C3 109.95(7) . . ? O3 S1 C3 108.89(7) . . ? O1 S1 C3 103.33(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.365 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.065 #===END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 736871' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 Cl2 Cu N6 O' _chemical_formula_sum 'C11 H12 Cl2 Cu N6 O' _chemical_formula_weight 378.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.902(5) _cell_length_b 13.026(5) _cell_length_c 16.7628(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3253.9(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4073 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.07 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 1.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7303 _exptl_absorpt_correction_T_max 0.8241 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17189 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 28.77 _reflns_number_total 4202 _reflns_number_gt 2966 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0609P)^2^+0.7249P] 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 4202 _refine_ls_number_parameters 187 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.396 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.250 0.031 0.505 134.3 24.7 2 0.250 -0.010 1.005 134.3 25.0 3 0.750 0.030 0.995 134.3 24.9 4 0.750 -0.010 0.495 134.3 25.1 _platon_squeeze_details ; ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4687(2) 0.8076(3) 0.79688(19) 0.0228(7) Uani 1 1 d . . . C2 C 0.4418(3) 0.8363(3) 0.8823(2) 0.0316(8) Uani 1 1 d . . . H2A H 0.4634 0.7840 0.9187 0.038 Uiso 1 1 calc R . . H2B H 0.4700 0.9008 0.8966 0.038 Uiso 1 1 calc R . . C11 C 0.3964(3) 0.5855(3) 0.6962(3) 0.0405(10) Uani 1 1 d . . . H11 H 0.3891 0.5454 0.6507 0.049 Uiso 1 1 calc R . . C12 C 0.3689(3) 0.5567(3) 0.7718(3) 0.0440(11) Uani 1 1 d . . . H12 H 0.3403 0.4961 0.7865 0.053 Uiso 1 1 calc R . . C13 C 0.3928(3) 0.6361(3) 0.8199(3) 0.0348(9) Uani 1 1 d . . . H13 H 0.3844 0.6395 0.8748 0.042 Uiso 1 1 calc R . . C14 C 0.6918(3) 0.7753(3) 0.7370(2) 0.0349(9) Uani 1 1 d . . . H14 H 0.7357 0.7595 0.6996 0.042 Uiso 1 1 calc R . . C15 C 0.7093(3) 0.8021(3) 0.8153(3) 0.0375(9) Uani 1 1 d . . . H15 H 0.7653 0.8077 0.8394 0.045 Uiso 1 1 calc R . . C16 C 0.6288(3) 0.8183(3) 0.8495(2) 0.0302(8) Uani 1 1 d . . . H16 H 0.6183 0.8371 0.9022 0.036 Uiso 1 1 calc R . . C17 C 0.4192(3) 0.9609(3) 0.6296(2) 0.0346(9) Uani 1 1 d . . . H17 H 0.4199 0.9749 0.5752 0.042 Uiso 1 1 calc R . . C18 C 0.3831(3) 1.0251(3) 0.6861(2) 0.0370(9) Uani 1 1 d . . . H18 H 0.3565 1.0888 0.6778 0.044 Uiso 1 1 calc R . . C19 C 0.3945(3) 0.9755(3) 0.7568(2) 0.0312(8) Uani 1 1 d . . . H19 H 0.3768 0.9993 0.8067 0.037 Uiso 1 1 calc R . . N11 N 0.4342(2) 0.6773(2) 0.69692(18) 0.0322(7) Uani 1 1 d . . . N13 N 0.4309(2) 0.7090(2) 0.77403(17) 0.0255(6) Uani 1 1 d . . . N14 N 0.6046(2) 0.7749(3) 0.72218(17) 0.0287(7) Uani 1 1 d . . . N16 N 0.5658(2) 0.8020(2) 0.79239(16) 0.0246(6) Uani 1 1 d . . . N17 N 0.4527(2) 0.8772(2) 0.66194(17) 0.0272(7) Uani 1 1 d . . . N19 N 0.4357(2) 0.8860(2) 0.74166(17) 0.0236(6) Uani 1 1 d . . . O1 O 0.3482 0.8457 0.8904 0.0394(7) Uani 1 1 d D . . Cl1 Cl 0.55733(9) 0.60643(8) 0.56010(6) 0.0445(3) Uani 1 1 d . . . Cl2 Cl 0.57090(9) 0.84709(9) 0.51532(6) 0.0472(3) Uani 1 1 d . . . Cu1 Cu 0.51331(3) 0.75326(3) 0.61710(2) 0.02816(16) Uani 1 1 d . . . H1 H 0.3289 0.7993 0.9265 0.042 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0222(18) 0.0249(18) 0.0213(15) 0.0022(14) -0.0035(13) -0.0005(14) C2 0.030(2) 0.039(2) 0.0256(17) -0.0031(16) -0.0014(15) 0.0003(17) C11 0.042(2) 0.026(2) 0.053(3) -0.0102(19) -0.003(2) -0.0059(18) C12 0.042(3) 0.024(2) 0.066(3) 0.001(2) 0.012(2) -0.0076(18) C13 0.036(2) 0.027(2) 0.042(2) 0.0065(17) 0.0079(17) -0.0009(17) C14 0.030(2) 0.036(2) 0.038(2) 0.0065(17) 0.0064(17) 0.0025(17) C15 0.0203(19) 0.046(2) 0.046(2) 0.006(2) -0.0054(17) -0.0049(17) C16 0.031(2) 0.032(2) 0.0269(17) 0.0009(16) -0.0073(15) -0.0020(16) C17 0.044(2) 0.027(2) 0.033(2) 0.0058(16) -0.0052(17) 0.0039(18) C18 0.042(2) 0.0239(19) 0.045(2) 0.0022(17) -0.0039(18) 0.0074(17) C19 0.036(2) 0.0251(18) 0.0327(19) -0.0036(16) -0.0022(16) 0.0048(16) N11 0.040(2) 0.0264(16) 0.0300(16) -0.0034(13) -0.0023(14) -0.0048(14) N13 0.0293(16) 0.0218(14) 0.0255(14) 0.0011(12) -0.0011(12) -0.0026(13) N14 0.0274(17) 0.0328(18) 0.0260(15) 0.0003(13) 0.0036(12) 0.0045(13) N16 0.0222(15) 0.0282(16) 0.0234(14) 0.0014(12) 0.0001(11) 0.0013(12) N17 0.0348(17) 0.0250(15) 0.0219(14) 0.0027(12) -0.0035(13) 0.0046(13) N19 0.0283(16) 0.0200(14) 0.0224(14) -0.0007(12) -0.0053(11) 0.0023(12) O1 0.0291(15) 0.0457(18) 0.0434(16) 0.0030(14) 0.0121(12) 0.0031(13) Cl1 0.0750(8) 0.0278(5) 0.0307(5) -0.0002(4) 0.0057(5) 0.0118(5) Cl2 0.0731(8) 0.0323(5) 0.0363(5) 0.0056(4) 0.0160(5) 0.0004(5) Cu1 0.0408(3) 0.0222(3) 0.0215(2) 0.00003(18) -0.00066(17) 0.0031(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 C1 N16 1.451(5) . ? C1 N13 1.454(5) . ? C1 N19 1.464(4) . ? C1 C2 1.533(5) . ? C2 O1 1.406 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C11 N11 1.321(5) . ? C11 C12 1.383(6) . ? C11 H11 0.9300 . ? C12 C13 1.359(6) . ? C12 H12 0.9300 . ? C13 N13 1.348(5) . ? C13 H13 0.9300 . ? C14 N14 1.322(5) . ? C14 C15 1.383(6) . ? C14 H14 0.9300 . ? C15 C16 1.347(6) . ? C15 H15 0.9300 . ? C16 N16 1.357(5) . ? C16 H16 0.9300 . ? C17 N17 1.316(5) . ? C17 C18 1.374(6) . ? C17 H17 0.9300 . ? C18 C19 1.360(5) . ? C18 H18 0.9300 . ? C19 N19 1.342(5) . ? C19 H19 0.9300 . ? N11 N13 1.358(4) . ? N11 Cu1 2.040(3) . ? N14 N16 1.358(4) . ? N14 Cu1 2.244(3) . ? N17 N19 1.365(4) . ? N17 Cu1 1.997(3) . ? O1 H1 0.90267 . ? Cl1 Cu1 2.2364(12) . ? Cl2 Cu1 2.2674(11) . ? 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 N16 C1 N13 109.2(3) . . ? N16 C1 N19 109.7(3) . . ? N13 C1 N19 108.6(3) . . ? N16 C1 C2 108.8(3) . . ? N13 C1 C2 111.1(3) . . ? N19 C1 C2 109.4(3) . . ? O1 C2 C1 111.8 . . ? O1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? O1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N11 C11 C12 111.3(4) . . ? N11 C11 H11 124.4 . . ? C12 C11 H11 124.4 . . ? C13 C12 C11 105.0(4) . . ? C13 C12 H12 127.5 . . ? C11 C12 H12 127.5 . . ? N13 C13 C12 108.0(4) . . ? N13 C13 H13 126.0 . . ? C12 C13 H13 126.0 . . ? N14 C14 C15 111.4(4) . . ? N14 C14 H14 124.3 . . ? C15 C14 H14 124.3 . . ? C16 C15 C14 105.9(4) . . ? C16 C15 H15 127.0 . . ? C14 C15 H15 127.0 . . ? C15 C16 N16 107.0(3) . . ? C15 C16 H16 126.5 . . ? N16 C16 H16 126.5 . . ? N17 C17 C18 111.6(3) . . ? N17 C17 H17 124.2 . . ? C18 C17 H17 124.2 . . ? C19 C18 C17 105.3(4) . . ? C19 C18 H18 127.4 . . ? C17 C18 H18 127.4 . . ? N19 C19 C18 107.7(3) . . ? N19 C19 H19 126.1 . . ? C18 C19 H19 126.1 . . ? C11 N11 N13 105.6(3) . . ? C11 N11 Cu1 132.8(3) . . ? N13 N11 Cu1 119.8(2) . . ? C13 N13 N11 110.1(3) . . ? C13 N13 C1 129.5(3) . . ? N11 N13 C1 120.4(3) . . ? C14 N14 N16 104.7(3) . . ? C14 N14 Cu1 138.1(3) . . ? N16 N14 Cu1 117.1(2) . . ? C16 N16 N14 110.9(3) . . ? C16 N16 C1 130.2(3) . . ? N14 N16 C1 118.9(3) . . ? C17 N17 N19 105.3(3) . . ? C17 N17 Cu1 133.3(3) . . ? N19 N17 Cu1 121.3(2) . . ? C19 N19 N17 110.1(3) . . ? C19 N19 C1 129.8(3) . . ? N17 N19 C1 119.9(3) . . ? C2 O1 H1 108.82 . . ? N17 Cu1 N11 83.36(13) . . ? N17 Cu1 Cl1 170.07(10) . . ? N11 Cu1 Cl1 91.99(10) . . ? N17 Cu1 N14 82.93(12) . . ? N11 Cu1 N14 84.08(12) . . ? Cl1 Cu1 N14 105.38(9) . . ? N17 Cu1 Cl2 91.05(10) . . ? N11 Cu1 Cl2 166.89(11) . . ? Cl1 Cu1 Cl2 91.63(5) . . ? N14 Cu1 Cl2 107.06(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.77 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.443 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.081 #===END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 736872' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 Cl4 Cu2 N12 O6 S2' _chemical_formula_sum 'C24 H28 Cl4 Cu2 N12 O6 S2' _chemical_formula_weight 913.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9521(7) _cell_length_b 18.7943(18) _cell_length_c 10.2236(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.085(6) _cell_angle_gamma 90.00 _cell_volume 1703.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1332 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 24.62 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5323 _exptl_absorpt_correction_T_max 0.6595 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11150 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.0815 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3119 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0283P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3119 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8884(5) 0.1353(2) 0.8357(4) 0.0182(10) Uani 1 1 d . . . C2 C 1.0412(5) 0.1648(2) 0.8107(4) 0.0264(11) Uani 1 1 d . . . H2A H 1.1179 0.1266 0.8159 0.032 Uiso 1 1 calc R . . H2B H 1.0334 0.1878 0.7229 0.032 Uiso 1 1 calc R . . C3 C 1.3453(5) 0.2633(3) 0.9890(5) 0.0377(13) Uani 1 1 d . . . H3A H 1.4122 0.3048 0.9964 0.056 Uiso 1 1 calc R . . H3B H 1.3927 0.2242 0.9466 0.056 Uiso 1 1 calc R . . H3C H 1.3272 0.2485 1.0773 0.056 Uiso 1 1 calc R . . C11 C 0.6773(5) 0.0098(2) 0.6335(4) 0.0240(11) Uani 1 1 d . . . H11 H 0.5947 -0.0220 0.6134 0.029 Uiso 1 1 calc R . . C12 C 0.7854(5) 0.0220(2) 0.5523(4) 0.0234(11) Uani 1 1 d . . . H12 H 0.7911 0.0009 0.4687 0.028 Uiso 1 1 calc R . . C13 C 0.8818(5) 0.0701(2) 0.6163(4) 0.0226(11) Uani 1 1 d . . . H13 H 0.9684 0.0896 0.5856 0.027 Uiso 1 1 calc R . . C14 C 0.8155(5) 0.0541(2) 1.1304(4) 0.0214(10) Uani 1 1 d . . . H14 H 0.7506 0.0337 1.1863 0.026 Uiso 1 1 calc R . . C15 C 0.9693(5) 0.0638(2) 1.1660(4) 0.0262(11) Uani 1 1 d . . . H15 H 1.0271 0.0523 1.2484 0.031 Uiso 1 1 calc R . . C16 C 1.0206(5) 0.0932(2) 1.0596(4) 0.0219(10) Uani 1 1 d . . . H16 H 1.1219 0.1062 1.0531 0.026 Uiso 1 1 calc R . . C17 C 0.7626(5) 0.2376(2) 0.9357(4) 0.0245(11) Uani 1 1 d . . . H17 H 0.8000 0.2307 1.0264 0.029 Uiso 1 1 calc R . . C18 C 0.6835(5) 0.2945(3) 0.8821(5) 0.0318(12) Uani 1 1 d . . . H18 H 0.6531 0.3352 0.9268 0.038 Uiso 1 1 calc R . . C19 C 0.6567(5) 0.2803(2) 0.7479(5) 0.0303(12) Uani 1 1 d . . . H19 H 0.6017 0.3112 0.6851 0.036 Uiso 1 1 calc R . . N11 N 0.7037(4) 0.04848(18) 0.7438(3) 0.0197(8) Uani 1 1 d . . . N13 N 0.8321(4) 0.08503(18) 0.7319(3) 0.0174(8) Uani 1 1 d . . . N14 N 0.7705(4) 0.07685(17) 1.0081(3) 0.0173(8) Uani 1 1 d . . . N16 N 0.8997(4) 0.10041(18) 0.9642(3) 0.0162(8) Uani 1 1 d . . . N17 N 0.7783(4) 0.19222(18) 0.8351(3) 0.0176(8) Uani 1 1 d . . . N19 N 0.7162(4) 0.21889(19) 0.7164(4) 0.0258(9) Uani 1 1 d . . . O1 O 1.0787(4) 0.21622(17) 0.9152(3) 0.0334(9) Uani 1 1 d . . . O2 O 1.1913(4) 0.29101(17) 0.7579(3) 0.0353(9) Uani 1 1 d . . . O3 O 1.1055(4) 0.34087(17) 0.9575(3) 0.0360(9) Uani 1 1 d . . . S1 S 1.17518(13) 0.28517(6) 0.89471(12) 0.0234(3) Uani 1 1 d . . . Cl1 Cl 0.37731(12) 0.08814(6) 0.73610(11) 0.0274(3) Uani 1 1 d . . . Cl2 Cl 0.44063(12) 0.07738(5) 1.06302(11) 0.0215(3) Uani 1 1 d . . . Cu1 Cu 0.57500(6) 0.06330(3) 0.88909(5) 0.01730(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(2) 0.018(2) 0.019(2) -0.0017(19) 0.0056(19) 0.0026(18) C2 0.026(3) 0.022(3) 0.032(3) -0.005(2) 0.009(2) -0.006(2) C3 0.022(3) 0.035(3) 0.054(4) 0.001(3) -0.001(2) -0.002(2) C11 0.022(3) 0.021(3) 0.026(3) -0.001(2) -0.006(2) 0.002(2) C12 0.033(3) 0.024(3) 0.013(2) -0.006(2) 0.001(2) 0.005(2) C13 0.031(3) 0.019(3) 0.020(2) 0.003(2) 0.012(2) 0.005(2) C14 0.027(3) 0.020(3) 0.016(2) 0.003(2) 0.0002(19) -0.0030(19) C15 0.029(3) 0.022(3) 0.022(2) 0.005(2) -0.011(2) 0.002(2) C16 0.013(2) 0.018(2) 0.033(3) 0.002(2) -0.003(2) 0.0001(18) C17 0.020(3) 0.030(3) 0.025(3) -0.008(2) 0.006(2) -0.001(2) C18 0.027(3) 0.024(3) 0.046(3) -0.005(2) 0.009(2) -0.001(2) C19 0.034(3) 0.023(3) 0.033(3) 0.010(2) 0.002(2) 0.008(2) N11 0.017(2) 0.020(2) 0.021(2) -0.0035(17) -0.0005(16) -0.0002(16) N13 0.0151(19) 0.017(2) 0.020(2) -0.0024(16) 0.0018(15) 0.0005(15) N14 0.0148(19) 0.017(2) 0.0207(19) 0.0035(16) 0.0039(15) -0.0019(15) N16 0.0112(19) 0.017(2) 0.020(2) 0.0042(16) -0.0001(15) -0.0008(15) N17 0.022(2) 0.0120(19) 0.019(2) 0.0005(16) 0.0053(16) 0.0027(15) N19 0.033(2) 0.024(2) 0.020(2) 0.0048(18) 0.0017(17) 0.0084(18) O1 0.038(2) 0.034(2) 0.031(2) -0.0099(16) 0.0132(16) -0.0215(16) O2 0.049(2) 0.027(2) 0.032(2) 0.0068(16) 0.0124(17) -0.0013(16) O3 0.038(2) 0.0261(19) 0.044(2) -0.0099(17) 0.0064(17) 0.0130(15) S1 0.0227(6) 0.0179(6) 0.0308(7) 0.0008(5) 0.0082(5) -0.0008(5) Cl1 0.0185(6) 0.0328(7) 0.0296(6) 0.0087(5) -0.0014(5) 0.0031(5) Cl2 0.0207(6) 0.0160(6) 0.0294(6) -0.0033(5) 0.0091(5) -0.0016(4) Cu1 0.0136(3) 0.0175(3) 0.0206(3) -0.0008(2) 0.0018(2) -0.0003(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 C1 N17 1.454(5) . ? C1 N13 1.457(5) . ? C1 N16 1.459(5) . ? C1 C2 1.530(6) . ? C2 O1 1.444(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 S1 1.733(4) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C11 N11 1.335(5) . ? C11 C12 1.380(6) . ? C11 H11 0.9500 . ? C12 C13 1.353(6) . ? C12 H12 0.9500 . ? C13 N13 1.350(5) . ? C13 H13 0.9500 . ? C14 N14 1.330(5) . ? C14 C15 1.385(6) . ? C14 H14 0.9500 . ? C15 C16 1.356(6) . ? C15 H15 0.9500 . ? C16 N16 1.359(5) . ? C16 H16 0.9500 . ? C17 C18 1.355(6) . ? C17 N17 1.358(5) . ? C17 H17 0.9500 . ? C18 C19 1.385(6) . ? C18 H18 0.9500 . ? C19 N19 1.329(5) . ? C19 H19 0.9500 . ? N11 N13 1.359(5) . ? N11 Cu1 2.023(4) . ? N14 N16 1.372(4) . ? N14 Cu1 2.002(3) . ? N17 N19 1.357(5) . ? O1 S1 1.588(3) . ? O2 S1 1.430(3) . ? O3 S1 1.418(3) . ? Cl1 Cu1 2.2400(11) . ? Cl2 Cu1 2.2980(12) . ? Cl2 Cu1 2.6962(12) 3_657 ? Cu1 Cl2 2.6962(12) 3_657 ? 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 N17 C1 N13 108.0(3) . . ? N17 C1 N16 107.2(3) . . ? N13 C1 N16 109.7(3) . . ? N17 C1 C2 110.8(4) . . ? N13 C1 C2 109.9(3) . . ? N16 C1 C2 111.3(3) . . ? O1 C2 C1 103.8(3) . . ? O1 C2 H2A 111.0 . . ? C1 C2 H2A 111.0 . . ? O1 C2 H2B 111.0 . . ? C1 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? S1 C3 H3A 109.5 . . ? S1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? S1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N11 C11 C12 111.2(4) . . ? N11 C11 H11 124.4 . . ? C12 C11 H11 124.4 . . ? C13 C12 C11 105.9(4) . . ? C13 C12 H12 127.1 . . ? C11 C12 H12 127.1 . . ? N13 C13 C12 107.2(4) . . ? N13 C13 H13 126.4 . . ? C12 C13 H13 126.4 . . ? N14 C14 C15 111.3(4) . . ? N14 C14 H14 124.4 . . ? C15 C14 H14 124.4 . . ? C16 C15 C14 106.2(4) . . ? C16 C15 H15 126.9 . . ? C14 C15 H15 126.9 . . ? C15 C16 N16 106.9(4) . . ? C15 C16 H16 126.5 . . ? N16 C16 H16 126.5 . . ? C18 C17 N17 107.1(4) . . ? C18 C17 H17 126.5 . . ? N17 C17 H17 126.5 . . ? C17 C18 C19 104.8(4) . . ? C17 C18 H18 127.6 . . ? C19 C18 H18 127.6 . . ? N19 C19 C18 112.8(4) . . ? N19 C19 H19 123.6 . . ? C18 C19 H19 123.6 . . ? C11 N11 N13 104.6(4) . . ? C11 N11 Cu1 130.1(3) . . ? N13 N11 Cu1 124.9(3) . . ? C13 N13 N11 111.1(3) . . ? C13 N13 C1 130.5(4) . . ? N11 N13 C1 118.3(3) . . ? C14 N14 N16 104.7(3) . . ? C14 N14 Cu1 130.9(3) . . ? N16 N14 Cu1 123.2(3) . . ? C16 N16 N14 110.8(3) . . ? C16 N16 C1 129.7(4) . . ? N14 N16 C1 119.0(3) . . ? N19 N17 C17 111.8(3) . . ? N19 N17 C1 117.9(3) . . ? C17 N17 C1 126.9(3) . . ? C19 N19 N17 103.4(4) . . ? C2 O1 S1 121.5(3) . . ? O3 S1 O2 119.8(2) . . ? O3 S1 O1 105.1(2) . . ? O2 S1 O1 108.87(18) . . ? O3 S1 C3 109.3(2) . . ? O2 S1 C3 111.1(2) . . ? O1 S1 C3 100.7(2) . . ? Cu1 Cl2 Cu1 94.23(4) . 3_657 ? N14 Cu1 N11 85.66(14) . . ? N14 Cu1 Cl1 159.23(10) . . ? N11 Cu1 Cl1 89.53(10) . . ? N14 Cu1 Cl2 91.32(10) . . ? N11 Cu1 Cl2 176.52(10) . . ? Cl1 Cu1 Cl2 93.91(5) . . ? N14 Cu1 Cl2 94.45(10) . 3_657 ? N11 Cu1 Cl2 92.73(10) . 3_657 ? Cl1 Cu1 Cl2 105.97(4) . 3_657 ? Cl2 Cu1 Cl2 85.77(4) . 3_657 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N17 C1 C2 O1 57.6(4) . . . . ? N13 C1 C2 O1 176.8(3) . . . . ? N16 C1 C2 O1 -61.6(4) . . . . ? N11 C11 C12 C13 0.1(5) . . . . ? C11 C12 C13 N13 0.5(5) . . . . ? N14 C14 C15 C16 -0.7(5) . . . . ? C14 C15 C16 N16 0.0(5) . . . . ? N17 C17 C18 C19 -0.8(5) . . . . ? C17 C18 C19 N19 -0.8(6) . . . . ? C12 C11 N11 N13 -0.6(5) . . . . ? C12 C11 N11 Cu1 171.7(3) . . . . ? C12 C13 N13 N11 -0.9(5) . . . . ? C12 C13 N13 C1 -176.8(4) . . . . ? C11 N11 N13 C13 1.0(4) . . . . ? Cu1 N11 N13 C13 -171.9(3) . . . . ? C11 N11 N13 C1 177.4(3) . . . . ? Cu1 N11 N13 C1 4.5(5) . . . . ? N17 C1 N13 C13 110.7(4) . . . . ? N16 C1 N13 C13 -132.8(4) . . . . ? C2 C1 N13 C13 -10.2(6) . . . . ? N17 C1 N13 N11 -64.9(4) . . . . ? N16 C1 N13 N11 51.6(4) . . . . ? C2 C1 N13 N11 174.2(3) . . . . ? C15 C14 N14 N16 1.1(5) . . . . ? C15 C14 N14 Cu1 168.3(3) . . . . ? C15 C16 N16 N14 0.7(5) . . . . ? C15 C16 N16 C1 173.1(4) . . . . ? C14 N14 N16 C16 -1.1(4) . . . . ? Cu1 N14 N16 C16 -169.5(3) . . . . ? C14 N14 N16 C1 -174.4(3) . . . . ? Cu1 N14 N16 C1 17.2(5) . . . . ? N17 C1 N16 C16 -119.3(4) . . . . ? N13 C1 N16 C16 123.7(4) . . . . ? C2 C1 N16 C16 2.0(6) . . . . ? N17 C1 N16 N14 52.6(4) . . . . ? N13 C1 N16 N14 -64.4(4) . . . . ? C2 C1 N16 N14 173.9(3) . . . . ? C18 C17 N17 N19 2.1(5) . . . . ? C18 C17 N17 C1 160.7(4) . . . . ? N13 C1 N17 N19 -43.3(5) . . . . ? N16 C1 N17 N19 -161.4(3) . . . . ? C2 C1 N17 N19 77.1(4) . . . . ? N13 C1 N17 C17 159.2(4) . . . . ? N16 C1 N17 C17 41.1(5) . . . . ? C2 C1 N17 C17 -80.4(5) . . . . ? C18 C19 N19 N17 2.0(5) . . . . ? C17 N17 N19 C19 -2.5(5) . . . . ? C1 N17 N19 C19 -163.3(4) . . . . ? C1 C2 O1 S1 -148.8(3) . . . . ? C2 O1 S1 O3 139.0(3) . . . . ? C2 O1 S1 O2 9.5(4) . . . . ? C2 O1 S1 C3 -107.4(4) . . . . ? C14 N14 Cu1 N11 -138.8(4) . . . . ? N16 N14 Cu1 N11 26.3(3) . . . . ? C14 N14 Cu1 Cl1 144.2(3) . . . . ? N16 N14 Cu1 Cl1 -50.8(5) . . . . ? C14 N14 Cu1 Cl2 39.5(4) . . . . ? N16 N14 Cu1 Cl2 -155.4(3) . . . . ? C14 N14 Cu1 Cl2 -46.3(4) . . . 3_657 ? N16 N14 Cu1 Cl2 118.7(3) . . . 3_657 ? C11 N11 Cu1 N14 151.0(4) . . . . ? N13 N11 Cu1 N14 -38.0(3) . . . . ? C11 N11 Cu1 Cl1 -49.2(4) . . . . ? N13 N11 Cu1 Cl1 121.8(3) . . . . ? C11 N11 Cu1 Cl2 56.8(4) . . . 3_657 ? N13 N11 Cu1 Cl2 -132.3(3) . . . 3_657 ? Cu1 Cl2 Cu1 N14 -94.36(10) 3_657 . . . ? Cu1 Cl2 Cu1 Cl1 105.75(4) 3_657 . . . ? Cu1 Cl2 Cu1 Cl2 0.0 3_657 . . 3_657 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.460 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.103