data_1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H33 Cl Cu N3 O6 S, Cl O4' _chemical_formula_sum 'C22 H33 Cl2 Cu N3 O10 S' _chemical_formula_weight 666.01 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5031(2) _cell_length_b 9.9656(3) _cell_length_c 16.9854(5) _cell_angle_alpha 93.826(3) _cell_angle_beta 95.153(2) _cell_angle_gamma 99.590(3) _cell_volume 1408.57(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9489 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 27.62 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 690 _exptl_absorpt_coefficient_mu 1.097 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.605 _exptl_absorpt_correction_T_max 0.860 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.989 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19209 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6467 _reflns_number_gt 5847 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL v6.10 (Sheldrick, 2008)' _computing_publication_material 'SHELXTL v6.10 (Sheldrick, 2008)' _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^)+(0.0347P)^2^+0.8853P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6467 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.64126(2) 0.911562(18) 0.209432(11) 0.01384(6) Uani 1 1 d . . . S2 S 0.91633(5) 1.04094(4) 0.19000(2) 0.02097(9) Uani 1 1 d . . . C1 C 0.72109(19) 0.62718(16) 0.19519(9) 0.0177(3) Uani 1 1 d . . . H1 H 0.7182 0.6343 0.1396 0.021 Uiso 1 1 calc R . . C2 C 0.76552(19) 0.51237(16) 0.22539(10) 0.0175(3) Uani 1 1 d . . . C3 C 0.76634(19) 0.50453(15) 0.30732(9) 0.0164(3) Uani 1 1 d . . . C4 C 0.71467(19) 0.60433(16) 0.35550(9) 0.0159(3) Uani 1 1 d . . . C5 C 0.67658(18) 0.71723(15) 0.31907(9) 0.0152(3) Uani 1 1 d . . . C6 C 0.6271(2) 0.83622(16) 0.36377(9) 0.0184(3) Uani 1 1 d . . . H6A H 0.5087 0.8239 0.3611 0.022 Uiso 1 1 calc R . . H6B H 0.6706 0.8425 0.4202 0.022 Uiso 1 1 calc R . . C7 C 0.60852(19) 1.07721(16) 0.35305(9) 0.0163(3) Uani 1 1 d . . . H7A H 0.6898 1.1555 0.3771 0.020 Uiso 1 1 calc R . . H7B H 0.5378 1.0471 0.3941 0.020 Uiso 1 1 calc R . . C8 C 0.51020(18) 1.12233(15) 0.28471(9) 0.0140(3) Uani 1 1 d . . . C9 C 0.41518(18) 1.22133(15) 0.29812(9) 0.0146(3) Uani 1 1 d . . . C10 C 0.33439(18) 1.26436(15) 0.23181(9) 0.0158(3) Uani 1 1 d . . . C11 C 0.34895(19) 1.20972(17) 0.15512(9) 0.0178(3) Uani 1 1 d . . . C12 C 0.44349(19) 1.11043(16) 0.14877(9) 0.0174(3) Uani 1 1 d . . . H12 H 0.4536 1.0709 0.0974 0.021 Uiso 1 1 calc R . . C13 C 0.8119(2) 0.40146(18) 0.17249(11) 0.0251(4) Uani 1 1 d . . . H13A H 0.7373 0.3160 0.1750 0.038 Uiso 1 1 calc R . . H13B H 0.9210 0.3890 0.1902 0.038 Uiso 1 1 calc R . . H13C H 0.8077 0.4272 0.1177 0.038 Uiso 1 1 calc R . . C14 C 0.9683(2) 0.42844(19) 0.38776(11) 0.0256(4) Uani 1 1 d . . . H14A H 1.0553 0.4303 0.3535 0.038 Uiso 1 1 calc R . . H14B H 0.9763 0.3596 0.4258 0.038 Uiso 1 1 calc R . . H14C H 0.9766 0.5184 0.4165 0.038 Uiso 1 1 calc R . . C15 C 0.6983(2) 0.59186(17) 0.44226(10) 0.0201(3) Uani 1 1 d . . . H15A H 0.7100 0.4995 0.4554 0.030 Uiso 1 1 calc R . . H15B H 0.5925 0.6093 0.4541 0.030 Uiso 1 1 calc R . . H15C H 0.7817 0.6586 0.4739 0.030 Uiso 1 1 calc R . . C16 C 0.3992(2) 1.27668(17) 0.38088(10) 0.0198(3) Uani 1 1 d . . . H16A H 0.3333 1.2069 0.4076 0.030 Uiso 1 1 calc R . . H16B H 0.3481 1.3577 0.3787 0.030 Uiso 1 1 calc R . . H16C H 0.5058 1.3015 0.4104 0.030 Uiso 1 1 calc R . . C17 C 0.2925(3) 1.49288(19) 0.22720(16) 0.0402(5) Uani 1 1 d . . . H17A H 0.2122 1.5503 0.2373 0.060 Uiso 0.50 1 calc PR . . H17B H 0.3142 1.4944 0.1715 0.060 Uiso 0.50 1 calc PR . . H17C H 0.3917 1.5279 0.2616 0.060 Uiso 0.50 1 calc PR . . H17D H 0.3999 1.4981 0.2096 0.060 Uiso 0.50 1 calc PR . . H17E H 0.2979 1.5540 0.2754 0.060 Uiso 0.50 1 calc PR . . H17F H 0.2204 1.5205 0.1854 0.060 Uiso 0.50 1 calc PR . . C18 C 0.2606(2) 1.2512(2) 0.08271(10) 0.0271(4) Uani 1 1 d . . . H18A H 0.2634 1.1854 0.0375 0.041 Uiso 1 1 calc R . . H18B H 0.3118 1.3422 0.0710 0.041 Uiso 1 1 calc R . . H18C H 0.1490 1.2529 0.0923 0.041 Uiso 1 1 calc R . . C19 C 0.86784(19) 0.99694(16) 0.34770(9) 0.0177(3) Uani 1 1 d . . . H19A H 0.9135 0.9120 0.3433 0.021 Uiso 1 1 calc R . . H19B H 0.8907 1.0361 0.4035 0.021 Uiso 1 1 calc R . . C20 C 0.9491(2) 1.09761(18) 0.29443(10) 0.0229(3) Uani 1 1 d . . . H20A H 1.0658 1.1155 0.3108 0.027 Uiso 1 1 calc R . . H20B H 0.9095 1.1850 0.3025 0.027 Uiso 1 1 calc R . . C21 C 1.0365(2) 0.90742(19) 0.18108(10) 0.0237(3) Uani 1 1 d . . . H21A H 1.1516 0.9460 0.1944 0.028 Uiso 1 1 calc R . . H21B H 1.0054 0.8367 0.2177 0.028 Uiso 1 1 calc R . . C22 C 1.0060(2) 0.8461(2) 0.09587(12) 0.0348(5) Uani 1 1 d . . . H22A H 0.8904 0.8187 0.0814 0.052 Uiso 1 1 calc R . . H22B H 1.0583 0.7659 0.0903 0.052 Uiso 1 1 calc R . . H22C H 1.0497 0.9140 0.0608 0.052 Uiso 1 1 calc R . . N1 N 0.68156(16) 0.72965(13) 0.24085(8) 0.0158(3) Uani 1 1 d . . . N2 N 0.69077(15) 0.96301(13) 0.32710(7) 0.0138(2) Uani 1 1 d . . . N3 N 0.52229(16) 1.06681(13) 0.21199(8) 0.0150(3) Uani 1 1 d . . . O1 O 0.81595(15) 0.39472(11) 0.33983(7) 0.0214(2) Uani 1 1 d . . . O2 O 0.23311(14) 1.35572(12) 0.24358(7) 0.0196(2) Uani 1 1 d . . . Cl1 Cl 0.42408(5) 0.76108(4) 0.07038(2) 0.02039(9) Uani 1 1 d . . . O3 O 0.58475(14) 0.84870(12) 0.09387(7) 0.0192(2) Uani 1 1 d . . . O4 O 0.33959(15) 0.75670(14) 0.13990(8) 0.0273(3) Uani 1 1 d . . . O5 O 0.44937(19) 0.62863(15) 0.04373(10) 0.0409(4) Uani 1 1 d . . . O6 O 0.34497(17) 0.82376(16) 0.00904(8) 0.0341(3) Uani 1 1 d . . . Cl2 Cl 0.79636(5) 1.18595(5) 0.56889(2) 0.02488(10) Uani 1 1 d . . . O7 O 0.7147(2) 1.04918(18) 0.54624(13) 0.0624(5) Uani 1 1 d . . . O8 O 0.8230(3) 1.2080(3) 0.65218(10) 0.0764(7) Uani 1 1 d . . . O9 O 0.69911(19) 1.27896(18) 0.53878(10) 0.0456(4) Uani 1 1 d . . . O10 O 0.94509(18) 1.20433(16) 0.53462(10) 0.0415(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01656(10) 0.01391(10) 0.01216(10) 0.00054(7) 0.00219(7) 0.00572(7) S2 0.0193(2) 0.0227(2) 0.0224(2) 0.00598(16) 0.00646(15) 0.00416(16) C1 0.0216(8) 0.0175(7) 0.0148(7) 0.0000(6) 0.0040(6) 0.0049(6) C2 0.0179(7) 0.0154(7) 0.0190(8) -0.0017(6) 0.0014(6) 0.0037(6) C3 0.0167(7) 0.0117(7) 0.0203(8) 0.0021(6) 0.0000(6) 0.0017(6) C4 0.0165(7) 0.0143(7) 0.0160(7) 0.0010(6) 0.0018(6) 0.0006(6) C5 0.0163(7) 0.0132(7) 0.0159(7) 0.0005(6) 0.0032(6) 0.0013(6) C6 0.0268(8) 0.0142(7) 0.0163(7) 0.0022(6) 0.0091(6) 0.0052(6) C7 0.0206(8) 0.0149(7) 0.0149(7) -0.0008(6) 0.0016(6) 0.0081(6) C8 0.0152(7) 0.0124(7) 0.0148(7) 0.0017(5) 0.0032(5) 0.0019(5) C9 0.0145(7) 0.0141(7) 0.0155(7) 0.0009(6) 0.0032(6) 0.0024(6) C10 0.0148(7) 0.0142(7) 0.0195(7) 0.0034(6) 0.0044(6) 0.0035(6) C11 0.0185(8) 0.0193(7) 0.0166(7) 0.0050(6) 0.0026(6) 0.0045(6) C12 0.0200(8) 0.0197(7) 0.0135(7) 0.0026(6) 0.0038(6) 0.0047(6) C13 0.0333(10) 0.0202(8) 0.0236(9) -0.0028(7) 0.0040(7) 0.0110(7) C14 0.0273(9) 0.0248(9) 0.0252(9) 0.0006(7) -0.0045(7) 0.0099(7) C15 0.0259(8) 0.0177(7) 0.0175(8) 0.0046(6) 0.0045(6) 0.0038(6) C16 0.0237(8) 0.0191(8) 0.0181(8) -0.0012(6) 0.0024(6) 0.0090(6) C17 0.0336(11) 0.0173(9) 0.0741(16) 0.0091(9) 0.0189(11) 0.0077(8) C18 0.0314(10) 0.0368(10) 0.0171(8) 0.0064(7) 0.0012(7) 0.0167(8) C19 0.0161(7) 0.0194(7) 0.0175(7) -0.0003(6) -0.0005(6) 0.0050(6) C20 0.0210(8) 0.0195(8) 0.0264(9) -0.0023(7) 0.0044(7) -0.0009(6) C21 0.0161(8) 0.0314(9) 0.0245(9) 0.0002(7) 0.0023(6) 0.0071(7) C22 0.0255(10) 0.0543(13) 0.0258(10) -0.0058(9) 0.0036(7) 0.0138(9) N1 0.0186(6) 0.0146(6) 0.0149(6) 0.0010(5) 0.0035(5) 0.0043(5) N2 0.0159(6) 0.0121(6) 0.0142(6) 0.0013(5) 0.0023(5) 0.0045(5) N3 0.0164(6) 0.0151(6) 0.0145(6) 0.0022(5) 0.0034(5) 0.0041(5) O1 0.0273(6) 0.0127(5) 0.0235(6) 0.0017(4) -0.0044(5) 0.0053(5) O2 0.0192(6) 0.0172(5) 0.0255(6) 0.0054(5) 0.0063(5) 0.0087(4) Cl1 0.01987(19) 0.02266(19) 0.01829(18) -0.00102(15) 0.00086(14) 0.00432(15) O3 0.0183(6) 0.0232(6) 0.0156(5) -0.0008(4) 0.0028(4) 0.0024(5) O4 0.0226(6) 0.0350(7) 0.0263(7) 0.0100(5) 0.0077(5) 0.0050(5) O5 0.0405(8) 0.0257(7) 0.0533(10) -0.0159(7) 0.0016(7) 0.0058(6) O6 0.0290(7) 0.0521(9) 0.0211(6) 0.0098(6) -0.0046(5) 0.0078(6) Cl2 0.0229(2) 0.0314(2) 0.0225(2) 0.00873(16) 0.00359(15) 0.00746(17) O7 0.0540(11) 0.0357(9) 0.0947(16) 0.0129(10) 0.0207(10) -0.0106(8) O8 0.1020(17) 0.1248(19) 0.0184(8) 0.0037(10) -0.0015(9) 0.0711(15) O9 0.0379(9) 0.0541(10) 0.0514(10) 0.0228(8) 0.0014(7) 0.0218(8) O10 0.0272(7) 0.0435(9) 0.0564(10) 0.0122(7) 0.0157(7) 0.0041(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 1.9847(13) . ? Cu1 N1 1.9980(13) . ? Cu1 O3 2.0105(11) . ? Cu1 N2 2.0186(13) . ? Cu1 S2 2.5363(5) . ? S2 C20 1.8077(18) . ? S2 C21 1.8143(18) . ? C1 N1 1.346(2) . ? C1 C2 1.379(2) . ? C1 H1 0.9500 . ? C2 C3 1.398(2) . ? C2 C13 1.504(2) . ? C3 O1 1.3685(18) . ? C3 C4 1.398(2) . ? C4 C5 1.390(2) . ? C4 C15 1.504(2) . ? C5 N1 1.346(2) . ? C5 C6 1.504(2) . ? C6 N2 1.4885(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N2 1.4940(18) . ? C7 C8 1.506(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N3 1.339(2) . ? C8 C9 1.395(2) . ? C9 C10 1.396(2) . ? C9 C16 1.502(2) . ? C10 O2 1.3706(18) . ? C10 C11 1.402(2) . ? C11 C12 1.380(2) . ? C11 C18 1.501(2) . ? C12 N3 1.349(2) . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O1 1.443(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O2 1.431(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 N2 1.491(2) . ? C19 C20 1.518(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.516(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? Cl1 O5 1.4233(14) . ? Cl1 O6 1.4245(13) . ? Cl1 O4 1.4357(13) . ? Cl1 O3 1.4987(12) . ? Cl2 O8 1.4091(17) . ? Cl2 O10 1.4287(15) . ? Cl2 O9 1.4307(15) . ? Cl2 O7 1.4334(18) . ? 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 N1 152.73(5) . . ? N3 Cu1 O3 97.52(5) . . ? N1 Cu1 O3 94.53(5) . . ? N3 Cu1 N2 84.21(5) . . ? N1 Cu1 N2 82.58(5) . . ? O3 Cu1 N2 176.36(5) . . ? N3 Cu1 S2 98.91(4) . . ? N1 Cu1 S2 104.48(4) . . ? O3 Cu1 S2 94.31(3) . . ? N2 Cu1 S2 88.57(4) . . ? C20 S2 C21 103.51(8) . . ? C20 S2 Cu1 90.12(6) . . ? C21 S2 Cu1 103.44(6) . . ? N1 C1 C2 123.04(15) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 116.93(14) . . ? C1 C2 C13 121.34(15) . . ? C3 C2 C13 121.72(15) . . ? O1 C3 C4 120.05(14) . . ? O1 C3 C2 118.57(14) . . ? C4 C3 C2 121.37(14) . . ? C5 C4 C3 116.60(14) . . ? C5 C4 C15 120.72(14) . . ? C3 C4 C15 122.68(14) . . ? N1 C5 C4 122.85(14) . . ? N1 C5 C6 114.31(13) . . ? C4 C5 C6 122.84(14) . . ? N2 C6 C5 108.32(12) . . ? N2 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? N2 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? N2 C7 C8 111.66(12) . . ? N2 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N2 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? N3 C8 C9 122.49(14) . . ? N3 C8 C7 117.34(13) . . ? C9 C8 C7 120.14(13) . . ? C8 C9 C10 117.27(14) . . ? C8 C9 C16 120.86(14) . . ? C10 C9 C16 121.87(14) . . ? O2 C10 C9 118.42(14) . . ? O2 C10 C11 120.54(14) . . ? C9 C10 C11 120.94(14) . . ? C12 C11 C10 116.97(14) . . ? C12 C11 C18 120.66(15) . . ? C10 C11 C18 122.30(15) . . ? N3 C12 C11 123.17(14) . . ? N3 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C4 C15 H15A 109.5 . . ? C4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 C16 H16A 109.5 . . ? C9 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C9 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? O2 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? O2 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C11 C18 H18A 109.5 . . ? C11 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C11 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 112.59(13) . . ? N2 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? N2 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.8 . . ? C19 C20 S2 114.31(12) . . ? C19 C20 H20A 108.7 . . ? S2 C20 H20A 108.7 . . ? C19 C20 H20B 108.7 . . ? S2 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C22 C21 S2 107.11(13) . . ? C22 C21 H21A 110.3 . . ? S2 C21 H21A 110.3 . . ? C22 C21 H21B 110.3 . . ? S2 C21 H21B 110.3 . . ? H21A C21 H21B 108.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C5 N1 C1 118.95(13) . . ? C5 N1 Cu1 112.73(10) . . ? C1 N1 Cu1 128.18(11) . . ? C6 N2 C19 109.16(12) . . ? C6 N2 C7 110.50(12) . . ? C19 N2 C7 111.99(12) . . ? C6 N2 Cu1 103.96(9) . . ? C19 N2 Cu1 109.68(9) . . ? C7 N2 Cu1 111.23(9) . . ? C8 N3 C12 119.12(13) . . ? C8 N3 Cu1 114.85(10) . . ? C12 N3 Cu1 125.74(11) . . ? C3 O1 C14 113.67(12) . . ? C10 O2 C17 115.42(13) . . ? O5 Cl1 O6 111.65(10) . . ? O5 Cl1 O4 111.14(9) . . ? O6 Cl1 O4 111.59(8) . . ? O5 Cl1 O3 108.05(8) . . ? O6 Cl1 O3 107.38(8) . . ? O4 Cl1 O3 106.77(7) . . ? Cl1 O3 Cu1 117.36(6) . . ? O8 Cl2 O10 110.59(13) . . ? O8 Cl2 O9 109.59(11) . . ? O10 Cl2 O9 109.77(10) . . ? O8 Cl2 O7 110.09(15) . . ? O10 Cl2 O7 108.11(11) . . ? O9 Cl2 O7 108.66(12) . . ? 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 N3 Cu1 S2 C20 79.12(7) . . . . ? N1 Cu1 S2 C20 -86.75(7) . . . . ? O3 Cu1 S2 C20 177.44(7) . . . . ? N2 Cu1 S2 C20 -4.79(7) . . . . ? N3 Cu1 S2 C21 -176.96(7) . . . . ? N1 Cu1 S2 C21 17.17(7) . . . . ? O3 Cu1 S2 C21 -78.64(7) . . . . ? N2 Cu1 S2 C21 99.13(7) . . . . ? N1 C1 C2 C3 0.8(2) . . . . ? N1 C1 C2 C13 -178.78(15) . . . . ? C1 C2 C3 O1 -177.41(14) . . . . ? C13 C2 C3 O1 2.2(2) . . . . ? C1 C2 C3 C4 4.0(2) . . . . ? C13 C2 C3 C4 -176.44(15) . . . . ? O1 C3 C4 C5 175.76(14) . . . . ? C2 C3 C4 C5 -5.6(2) . . . . ? O1 C3 C4 C15 -4.9(2) . . . . ? C2 C3 C4 C15 173.67(15) . . . . ? C3 C4 C5 N1 2.8(2) . . . . ? C15 C4 C5 N1 -176.55(15) . . . . ? C3 C4 C5 C6 -176.90(15) . . . . ? C15 C4 C5 C6 3.8(2) . . . . ? N1 C5 C6 N2 -34.40(19) . . . . ? C4 C5 C6 N2 145.30(15) . . . . ? N2 C7 C8 N3 -6.55(19) . . . . ? N2 C7 C8 C9 175.38(13) . . . . ? N3 C8 C9 C10 -1.6(2) . . . . ? C7 C8 C9 C10 176.36(14) . . . . ? N3 C8 C9 C16 177.33(14) . . . . ? C7 C8 C9 C16 -4.7(2) . . . . ? C8 C9 C10 O2 176.34(13) . . . . ? C16 C9 C10 O2 -2.6(2) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C16 C9 C10 C11 -178.96(15) . . . . ? O2 C10 C11 C12 -175.00(14) . . . . ? C9 C10 C11 C12 1.3(2) . . . . ? O2 C10 C11 C18 2.2(2) . . . . ? C9 C10 C11 C18 178.46(15) . . . . ? C10 C11 C12 N3 -1.1(2) . . . . ? C18 C11 C12 N3 -178.29(15) . . . . ? N2 C19 C20 S2 -58.13(16) . . . . ? C21 S2 C20 C19 -72.05(14) . . . . ? Cu1 S2 C20 C19 31.81(12) . . . . ? C20 S2 C21 C22 175.72(13) . . . . ? Cu1 S2 C21 C22 82.31(13) . . . . ? C4 C5 N1 C1 1.7(2) . . . . ? C6 C5 N1 C1 -178.55(14) . . . . ? C4 C5 N1 Cu1 -174.29(12) . . . . ? C6 C5 N1 Cu1 5.42(17) . . . . ? C2 C1 N1 C5 -3.6(2) . . . . ? C2 C1 N1 Cu1 171.70(12) . . . . ? N3 Cu1 N1 C5 -44.82(18) . . . . ? O3 Cu1 N1 C5 -160.94(11) . . . . ? N2 Cu1 N1 C5 16.83(11) . . . . ? S2 Cu1 N1 C5 103.41(11) . . . . ? N3 Cu1 N1 C1 139.60(14) . . . . ? O3 Cu1 N1 C1 23.48(14) . . . . ? N2 Cu1 N1 C1 -158.75(15) . . . . ? S2 Cu1 N1 C1 -72.17(14) . . . . ? C5 C6 N2 C19 -72.45(16) . . . . ? C5 C6 N2 C7 163.96(13) . . . . ? C5 C6 N2 Cu1 44.53(14) . . . . ? C20 C19 N2 C6 163.05(13) . . . . ? C20 C19 N2 C7 -74.26(16) . . . . ? C20 C19 N2 Cu1 49.75(15) . . . . ? C8 C7 N2 C6 -114.54(14) . . . . ? C8 C7 N2 C19 123.53(14) . . . . ? C8 C7 N2 Cu1 0.40(15) . . . . ? N3 Cu1 N2 C6 122.38(10) . . . . ? N1 Cu1 N2 C6 -33.71(9) . . . . ? S2 Cu1 N2 C6 -138.51(9) . . . . ? N3 Cu1 N2 C19 -120.99(10) . . . . ? N1 Cu1 N2 C19 82.92(10) . . . . ? S2 Cu1 N2 C19 -21.88(9) . . . . ? N3 Cu1 N2 C7 3.45(10) . . . . ? N1 Cu1 N2 C7 -152.64(11) . . . . ? S2 Cu1 N2 C7 102.56(10) . . . . ? C9 C8 N3 C12 1.9(2) . . . . ? C7 C8 N3 C12 -176.14(14) . . . . ? C9 C8 N3 Cu1 -172.32(11) . . . . ? C7 C8 N3 Cu1 9.65(17) . . . . ? C11 C12 N3 C8 -0.5(2) . . . . ? C11 C12 N3 Cu1 173.03(12) . . . . ? N1 Cu1 N3 C8 53.97(18) . . . . ? O3 Cu1 N3 C8 169.44(11) . . . . ? N2 Cu1 N3 C8 -7.34(11) . . . . ? S2 Cu1 N3 C8 -94.97(11) . . . . ? N1 Cu1 N3 C12 -119.80(15) . . . . ? O3 Cu1 N3 C12 -4.33(13) . . . . ? N2 Cu1 N3 C12 178.89(13) . . . . ? S2 Cu1 N3 C12 91.26(13) . . . . ? C4 C3 O1 C14 -71.34(19) . . . . ? C2 C3 O1 C14 110.02(17) . . . . ? C9 C10 O2 C17 104.96(19) . . . . ? C11 C10 O2 C17 -78.7(2) . . . . ? O5 Cl1 O3 Cu1 -113.10(9) . . . . ? O6 Cl1 O3 Cu1 126.34(8) . . . . ? O4 Cl1 O3 Cu1 6.54(10) . . . . ? N3 Cu1 O3 Cl1 -80.99(8) . . . . ? N1 Cu1 O3 Cl1 74.50(8) . . . . ? S2 Cu1 O3 Cl1 179.42(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.660 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.076 _iucr_refine_instructions_details ; TITL x0915a in P-1 CELL 0.71073 8.5031 9.9656 16.9854 93.826 95.153 99.590 ZERR 2.00 0.0002 0.0003 0.0005 0.003 0.002 0.003 LATT 1 SFAC C H N O S CL CU UNIT 44 66 6 20 2 4 2 TEMP -123 ACTA HTAB BOND BOND $H CONF WPDB L.S. 6 FMAP 2 PLAN 10 OMIT -2 55 OMIT 0 1 0 WGHT 0.034700 0.885300 FVAR 4.73543 PART 0 rem Cu complex CU1 7 0.641256 0.911562 0.209432 11.00000 0.01656 0.01391 = 0.01216 0.00054 0.00219 0.00572 S2 5 0.916331 1.040939 0.190001 11.00000 0.01935 0.02271 = 0.02240 0.00598 0.00646 0.00416 C1 1 0.721090 0.627177 0.195190 11.00000 0.02160 0.01745 = 0.01478 0.00001 0.00404 0.00494 AFIX 43 H1 2 0.718248 0.634273 0.139600 11.00000 -1.20000 AFIX 0 C2 1 0.765517 0.512374 0.225393 11.00000 0.01787 0.01539 = 0.01903 -0.00165 0.00143 0.00374 C3 1 0.766344 0.504527 0.307318 11.00000 0.01669 0.01169 = 0.02027 0.00209 0.00001 0.00168 C4 1 0.714670 0.604333 0.355500 11.00000 0.01652 0.01434 = 0.01599 0.00104 0.00178 0.00061 C5 1 0.676581 0.717227 0.319068 11.00000 0.01633 0.01322 = 0.01588 0.00054 0.00315 0.00125 C6 1 0.627101 0.836215 0.363772 11.00000 0.02679 0.01420 = 0.01626 0.00221 0.00914 0.00520 AFIX 23 H6A 2 0.508729 0.823861 0.361113 11.00000 -1.20000 H6B 2 0.670623 0.842545 0.420203 11.00000 -1.20000 AFIX 0 C7 1 0.608520 1.077207 0.353054 11.00000 0.02060 0.01486 = 0.01493 -0.00081 0.00160 0.00810 AFIX 23 H7A 2 0.689806 1.155503 0.377067 11.00000 -1.20000 H7B 2 0.537830 1.047092 0.394083 11.00000 -1.20000 AFIX 0 C8 1 0.510195 1.122334 0.284712 11.00000 0.01517 0.01240 = 0.01476 0.00169 0.00324 0.00189 C9 1 0.415180 1.221331 0.298118 11.00000 0.01451 0.01412 = 0.01551 0.00092 0.00324 0.00243 C10 1 0.334387 1.264356 0.231808 11.00000 0.01482 0.01420 = 0.01948 0.00342 0.00437 0.00352 C11 1 0.348948 1.209719 0.155116 11.00000 0.01854 0.01934 = 0.01664 0.00503 0.00264 0.00450 C12 1 0.443490 1.110431 0.148773 11.00000 0.02003 0.01965 = 0.01347 0.00255 0.00381 0.00470 AFIX 43 H12 2 0.453603 1.070859 0.097423 11.00000 -1.20000 AFIX 0 C13 1 0.811910 0.401463 0.172486 11.00000 0.03327 0.02025 = 0.02363 -0.00280 0.00401 0.01103 AFIX 137 H13A 2 0.737279 0.315953 0.175029 11.00000 -1.50000 H13B 2 0.921034 0.388968 0.190205 11.00000 -1.50000 H13C 2 0.807651 0.427187 0.117746 11.00000 -1.50000 AFIX 0 C14 1 0.968256 0.428438 0.387760 11.00000 0.02725 0.02480 = 0.02521 0.00063 -0.00453 0.00987 AFIX 137 H14A 2 1.055294 0.430280 0.353526 11.00000 -1.50000 H14B 2 0.976322 0.359578 0.425818 11.00000 -1.50000 H14C 2 0.976594 0.518355 0.416493 11.00000 -1.50000 AFIX 0 C15 1 0.698285 0.591861 0.442264 11.00000 0.02595 0.01768 = 0.01755 0.00458 0.00449 0.00376 AFIX 137 H15A 2 0.710008 0.499514 0.455376 11.00000 -1.50000 H15B 2 0.592460 0.609335 0.454091 11.00000 -1.50000 H15C 2 0.781710 0.658607 0.473858 11.00000 -1.50000 AFIX 0 C16 1 0.399208 1.276681 0.380879 11.00000 0.02367 0.01911 = 0.01809 -0.00125 0.00235 0.00900 AFIX 137 H16A 2 0.333333 1.206932 0.407571 11.00000 -1.50000 H16B 2 0.348115 1.357722 0.378693 11.00000 -1.50000 H16C 2 0.505751 1.301514 0.410389 11.00000 -1.50000 AFIX 0 C17 1 0.292504 1.492875 0.227198 11.00000 0.03362 0.01728 = 0.07406 0.00907 0.01892 0.00770 AFIX 123 H17A 2 0.212248 1.550293 0.237270 10.50000 -1.50000 H17B 2 0.314242 1.494369 0.171543 10.50000 -1.50000 H17C 2 0.391707 1.527917 0.261563 10.50000 -1.50000 H17D 2 0.399883 1.498093 0.209647 10.50000 -1.50000 H17E 2 0.297889 1.554017 0.275375 10.50000 -1.50000 H17F 2 0.220425 1.520469 0.185354 10.50000 -1.50000 AFIX 0 C18 1 0.260600 1.251165 0.082709 11.00000 0.03142 0.03676 = 0.01709 0.00641 0.00125 0.01674 AFIX 137 H18A 2 0.263352 1.185405 0.037519 11.00000 -1.50000 H18B 2 0.311770 1.342239 0.071029 11.00000 -1.50000 H18C 2 0.148991 1.252912 0.092303 11.00000 -1.50000 AFIX 0 C19 1 0.867841 0.996939 0.347695 11.00000 0.01611 0.01942 = 0.01752 -0.00026 -0.00054 0.00503 AFIX 23 H19A 2 0.913538 0.911963 0.343307 11.00000 -1.20000 H19B 2 0.890697 1.036142 0.403469 11.00000 -1.20000 AFIX 0 C20 1 0.949064 1.097606 0.294428 11.00000 0.02102 0.01954 = 0.02639 -0.00234 0.00440 -0.00094 AFIX 23 H20A 2 1.065837 1.115499 0.310845 11.00000 -1.20000 H20B 2 0.909481 1.184979 0.302456 11.00000 -1.20000 AFIX 0 C21 1 1.036507 0.907422 0.181081 11.00000 0.01612 0.03139 = 0.02446 0.00024 0.00233 0.00711 AFIX 23 H21A 2 1.151620 0.945966 0.194384 11.00000 -1.20000 H21B 2 1.005423 0.836650 0.217699 11.00000 -1.20000 AFIX 0 C22 1 1.006023 0.846076 0.095872 11.00000 0.02549 0.05431 = 0.02583 -0.00585 0.00359 0.01378 AFIX 137 H22A 2 0.890351 0.818682 0.081424 11.00000 -1.50000 H22B 2 1.058318 0.765930 0.090312 11.00000 -1.50000 H22C 2 1.049690 0.913953 0.060788 11.00000 -1.50000 AFIX 0 N1 3 0.681563 0.729651 0.240846 11.00000 0.01859 0.01456 = 0.01492 0.00098 0.00346 0.00432 N2 3 0.690767 0.963014 0.327095 11.00000 0.01587 0.01213 = 0.01419 0.00134 0.00231 0.00454 N3 3 0.522293 1.066812 0.211988 11.00000 0.01636 0.01512 = 0.01446 0.00216 0.00337 0.00413 O1 4 0.815954 0.394724 0.339827 11.00000 0.02735 0.01270 = 0.02349 0.00168 -0.00438 0.00529 O2 4 0.233111 1.355721 0.243576 11.00000 0.01919 0.01724 = 0.02554 0.00537 0.00628 0.00873 CL1 6 0.424082 0.761083 0.070385 11.00000 0.01987 0.02266 = 0.01829 -0.00102 0.00086 0.00432 O3 4 0.584748 0.848703 0.093873 11.00000 0.01829 0.02320 = 0.01556 -0.00082 0.00281 0.00245 O4 4 0.339594 0.756699 0.139904 11.00000 0.02259 0.03501 = 0.02633 0.01002 0.00767 0.00501 O5 4 0.449373 0.628628 0.043734 11.00000 0.04047 0.02570 = 0.05330 -0.01586 0.00156 0.00576 O6 4 0.344966 0.823759 0.009044 11.00000 0.02895 0.05208 = 0.02110 0.00981 -0.00458 0.00782 REM ClO4- counterion CL2 6 0.796355 1.185954 0.568887 11.00000 0.02286 0.03138 = 0.02247 0.00873 0.00359 0.00746 O7 4 0.714680 1.049182 0.546242 11.00000 0.05399 0.03573 = 0.09468 0.01289 0.02066 -0.01055 O8 4 0.822963 1.208007 0.652182 11.00000 0.10201 0.12478 = 0.01840 0.00372 -0.00154 0.07106 O9 4 0.699107 1.278960 0.538781 11.00000 0.03789 0.05409 = 0.05143 0.02278 0.00145 0.02184 O10 4 0.945094 1.204326 0.534622 11.00000 0.02717 0.04354 = 0.05642 0.01220 0.01574 0.00406 HKLF 4 REM x0915a in P-1 REM R1 = 0.0276 for 5847 Fo > 4sig(Fo) and 0.0310 for all 6467 data REM 358 parameters refined using 0 restraints END WGHT 0.0347 0.8853 REM Highest difference peak 0.660, deepest hole -0.539, 1-sigma level 0.076 Q1 1 0.7385 1.0634 0.5985 11.00000 0.05 0.66 Q2 1 0.9132 1.2629 0.6504 11.00000 0.05 0.52 Q3 1 0.9443 1.2383 0.5746 11.00000 0.05 0.35 Q4 1 0.9114 1.2428 0.5092 11.00000 0.05 0.33 Q5 1 0.9063 1.0452 0.3183 11.00000 0.05 0.32 Q6 1 0.8335 1.2185 0.6086 11.00000 0.05 0.30 Q7 1 0.6954 1.3184 0.5730 11.00000 0.05 0.30 Q8 1 0.4701 1.1863 0.2928 11.00000 0.05 0.30 Q9 1 0.7808 0.9854 0.3355 11.00000 0.05 0.29 Q10 1 0.2990 1.2291 0.1246 11.00000 0.05 0.28 ;