# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1633 data_global #============================================================================== _audit_creation_method 'manual editing of form.cif' # PROCESSING SUMMARY (IUCr Office Use Only) _journal_data_validation_number ? _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _iucr_compatibility_tag ACTA95 _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_paper_category ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Jagadese J. Vittal' _publ_contact_author_address ; Department of Chemistry National University of Singapore Kent Ridge Singapore 119 260 ; _publ_contact_author_email chmjjv@nus.edu.sg _publ_contact_author_fax '(65) 874 2975' _publ_contact_author_phone '(65) 779 1691 ' _publ_contact_letter ; Please consider this CIF submission for publication in Inorganic Chemistry. ; _publ_requested_journal 'Dalton Transactions' _publ_requested_category FM # TITLE AND AUTHOR LIST _publ_section_title ; Preparation, characterisation and structures of copper(II) complexes of an asymmetric anticancer drug analogue ; _publ_section_title_footnote ; Contribution No. ... ; loop_ _publ_author_name _publ_author_address 'Moubaraki, Boujemaa' ; Chemistry Department Monash University Wellington Road Clayton, Victoria 3168 Australia ; 'Murray, Keith S.' ; Chemistry Department Monash University Wellington Road Clayton, Victoria 3168 Australia ; 'Ranford, John D.' ; Department of Chemistry National University of Singapore Kent Ridge Singapore 119 260 ; 'Vittal, Jagadese J.' ; Department of Chemistry National University of Singapore Kent Ridge Singapore 119 260 ; 'Wang, Xiaobai' ; Department of Chemistry National University of Singapore Kent Ridge Singapore 119 260 ; 'Xu, Yan' ; Department of Chemistry National Institute of Education 469, Bukit Timah Road Singapore 259 756 ; ############################################################# #compound 7 in the Text, please see CCDC No: 182/711 # B. Moubaraki, K.S. Murray, J.D. Ranford, X. Wang and Y.Xu, Chem. comm. # 1998, 353. # #compound 10 in the Text data_jdr1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C38 H22 Cu4 F18 N12 O12 S2' _chemical_formula_weight 1498.96 _chemical_melting_point ? _chemical_compound_source 'see text' 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' 'F' 'F' 0.0171 0.0103 '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' '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4999(2) _cell_length_b 12.2367(2) _cell_length_c 12.5765(3) _cell_angle_alpha 76.880(1) _cell_angle_beta 78.937(1) _cell_angle_gamma 67.718(1) _cell_volume 1308.37(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5530 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 55.70 _exptl_crystal_description 'triclinicy shape' _exptl_crystal_colour 'transparent green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.902 _exptl_crystal_density_method ? _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 1.818 _exptl_absorpt_correction_type 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.593 _exptl_absorpt_correction_T_max 0.773 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD' _diffrn_measurement_method 'frames \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7281 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.85 _reflns_number_total 5179 _reflns_number_observed 4500 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0875P)^2^+3.3313P] 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 ; riding models were used to place the hydrogen atoms in their idealized positions. ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5179 _refine_ls_number_parameters 460 _refine_ls_number_restraints 1074 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_obs 0.0573 _refine_ls_wR_factor_all 0.1631 _refine_ls_wR_factor_obs 0.1574 _refine_ls_goodness_of_fit_all 1.085 _refine_ls_goodness_of_fit_obs 1.130 _refine_ls_restrained_S_all 1.267 _refine_ls_restrained_S_obs 1.320 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 1.420 _refine_diff_density_min -0.894 _refine_diff_density_rms 0.112 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu -0.23973(8) 0.68775(6) 0.85961(5) 0.0339(2) Uani 1 d . . Cu2 Cu -0.48810(8) 0.64825(6) 0.56894(5) 0.0360(2) Uani 1 d . . S1 S -0.4703(2) 0.49916(13) 0.71930(11) 0.0388(3) Uani 1 d . . N1 N -0.1663(6) 0.6724(4) 1.0061(4) 0.0384(10) Uani 1 d . . N2 N -0.2579(5) 0.5343(4) 0.9353(3) 0.0330(9) Uani 1 d . . N3 N -0.3167(5) 0.4803(4) 0.8808(4) 0.0352(10) Uani 1 d . . H3A H -0.3259(5) 0.4117(4) 0.9073(4) 0.042 Uiso 1 calc R . N4 N -0.3113(5) 0.6359(4) 0.7422(3) 0.0320(9) Uani 1 d . . N5 N -0.3567(5) 0.6936(4) 0.6411(3) 0.0309(9) Uani 1 d . . N6 N -0.4665(6) 0.7898(4) 0.4554(4) 0.0413(11) Uani 1 d . . C1 C -0.1237(8) 0.7502(6) 1.0395(5) 0.0500(15) Uani 1 d . . H1 H -0.1129(8) 0.8160(6) 0.9892(5) 0.060 Uiso 1 calc R . C2 C -0.0951(9) 0.7360(7) 1.1467(6) 0.059(2) Uani 1 d . . H2 H -0.0633(9) 0.7902(7) 1.1677(6) 0.071 Uiso 1 calc R . C3 C -0.1149(9) 0.6399(7) 1.2214(6) 0.061(2) Uani 1 d . . H3 H -0.1004(9) 0.6307(7) 1.2944(6) 0.074 Uiso 1 calc R . C4 C -0.1560(8) 0.5575(7) 1.1881(5) 0.051(2) Uani 1 d . . H4 H -0.1669(8) 0.4911(7) 1.2373(5) 0.062 Uiso 1 calc R . C5 C -0.1809(6) 0.5761(5) 1.0789(4) 0.0374(12) Uani 1 d . . C6 C -0.2317(6) 0.4980(5) 1.0356(4) 0.0364(11) Uani 1 d . . H6 H -0.2439(6) 0.4283(5) 1.0773(4) 0.044 Uiso 1 calc R . C7 C -0.3598(6) 0.5433(4) 0.7814(4) 0.0306(10) Uani 1 d . . C8 C -0.3193(6) 0.7834(5) 0.5899(4) 0.0355(11) Uani 1 d . . H8 H -0.2611(6) 0.8129(5) 0.6194(4) 0.043 Uiso 1 calc R . C9 C -0.3731(6) 0.8368(5) 0.4824(4) 0.0355(11) Uani 1 d . . C10 C -0.3344(8) 0.9287(6) 0.4137(5) 0.0473(14) Uani 1 d . . H10 H -0.2690(8) 0.9589(6) 0.4338(5) 0.057 Uiso 1 calc R . C11 C -0.3944(8) 0.9754(6) 0.3142(6) 0.056(2) Uani 1 d . . H11 H -0.3700(8) 1.0376(6) 0.2666(6) 0.068 Uiso 1 calc R . C12 C -0.4908(9) 0.9282(7) 0.2870(6) 0.061(2) Uani 1 d . . H12 H -0.5333(9) 0.9587(7) 0.2210(6) 0.074 Uiso 1 calc R . C13 C -0.5234(8) 0.8351(6) 0.3588(6) 0.056(2) Uani 1 d . . H13 H -0.5871(8) 0.8027(6) 0.3395(6) 0.067 Uiso 1 calc R . O1 O -0.4697(5) 0.8164(4) 0.9073(4) 0.0506(11) Uani 1 d . . O2 O -0.5797(6) 0.6791(4) 0.9755(4) 0.0591(13) Uani 1 d . . C14 C -0.5705(6) 0.7787(4) 0.9616(4) 0.0394(12) Uani 1 d D . C15 C -0.7050(7) 0.8713(5) 1.0189(6) 0.081(3) Uani 1 d D . F1 F -0.8119(16) 0.9365(17) 0.9517(13) 0.139(16) Uani 0.35 d PD 1 F2 F -0.6595(14) 0.9480(14) 1.0517(17) 0.077(6) Uani 0.35 d PD 1 F3 F -0.7732(21) 0.8191(10) 1.1076(14) 0.135(17) Uani 0.35 d PD 1 F1A F -0.6639(16) 0.8972(27) 1.1032(20) 0.160(17) Uani 0.35 d PD 2 F2A F -0.8213(17) 0.8315(17) 1.0583(26) 0.114(12) Uani 0.35 d PD 2 F3A F -0.7598(29) 0.9740(13) 0.9497(14) 0.115(10) Uani 0.35 d PD 2 F1B F -0.6857(24) 0.9769(10) 1.0011(25) 0.107(10) Uani 0.30 d PD 3 F2B F -0.7200(28) 0.8352(16) 1.1280(7) 0.122(14) Uani 0.30 d PD 3 F3B F -0.8377(9) 0.8902(25) 0.9838(23) 0.188(27) Uani 0.30 d PD 3 O3 O -0.1729(5) 0.8163(4) 0.7747(3) 0.0445(10) Uani 1 d . . O4 O 0.0755(6) 0.7216(6) 0.7919(6) 0.086(2) Uani 1 d . . C16 C -0.0333(6) 0.8054(5) 0.7590(4) 0.0448(13) Uani 1 d D . C17 C -0.0044(5) 0.9184(5) 0.6922(4) 0.071(2) Uani 1 d D . F4 F 0.1448(6) 0.8969(7) 0.6610(10) 0.075(3) Uiso 0.45 d PD 4 F5 F -0.0576(15) 1.0086(6) 0.7482(8) 0.089(4) Uiso 0.45 d PD 4 F6 F -0.0741(13) 0.9559(9) 0.6002(7) 0.085(3) Uiso 0.45 d PD 4 F4A F 0.1229(10) 0.8923(7) 0.6218(8) 0.073(3) Uiso 0.40 d PD 5 F5A F -0.1199(10) 0.9908(8) 0.6356(10) 0.086(4) Uiso 0.40 d PD 5 F6A F 0.0128(16) 0.9822(8) 0.7601(7) 0.082(4) Uiso 0.40 d PD 5 F4B F 0.1177(24) 0.9297(18) 0.7201(22) 0.137(18) Uiso 0.15 d PD 6 F5B F -0.1236(17) 1.0180(6) 0.7070(22) 0.060(7) Uiso 0.15 d PD 6 F6B F 0.0223(40) 0.9146(16) 0.5844(5) 0.120(15) Uiso 0.15 d PD 6 O5 O -0.3270(5) 0.3345(4) 0.4850(4) 0.0461(10) Uani 1 d . . O6 O -0.3180(5) 0.5201(4) 0.4501(3) 0.0486(10) Uani 1 d . . C18 C -0.2699(5) 0.4111(5) 0.4813(4) 0.0393(12) Uani 1 d D . C19 C -0.1096(6) 0.3598(4) 0.5190(4) 0.070(2) Uani 1 d D . F7 F -0.0969(7) 0.4274(7) 0.5850(7) 0.061(2) Uiso 0.50 d PD 7 F8 F -0.0033(6) 0.3648(9) 0.4314(5) 0.068(2) Uiso 0.50 d PD 7 F9 F -0.0727(9) 0.2482(5) 0.5707(8) 0.103(4) Uiso 0.50 d PD 7 F7A F -0.0675(13) 0.4452(8) 0.5384(13) 0.116(8) Uiso 0.30 d PD 8 F8A F -0.1094(10) 0.2829(10) 0.6158(7) 0.056(3) Uiso 0.30 d PD 8 F9A F -0.0033(8) 0.2994(13) 0.4482(8) 0.114(7) Uiso 0.30 d PD 8 F7B F -0.0185(10) 0.4175(12) 0.4586(13) 0.094(8) Uiso 0.20 d PD 9 F8B F -0.0395(11) 0.2438(7) 0.5064(14) 0.039(3) Uiso 0.20 d PD 9 F9B F -0.1123(12) 0.3639(16) 0.6238(7) 0.121(11) Uiso 0.20 d PD 9 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 0.0432(4) 0.0363(4) 0.0279(3) 0.0048(2) -0.0102(3) -0.0232(3) Cu2 0.0411(4) 0.0381(4) 0.0355(4) 0.0017(3) -0.0146(3) -0.0209(3) S1 0.0492(8) 0.0443(7) 0.0341(7) -0.0008(6) -0.0083(6) -0.0305(6) N1 0.046(3) 0.043(2) 0.032(2) 0.000(2) -0.010(2) -0.022(2) N2 0.038(2) 0.034(2) 0.029(2) 0.002(2) -0.008(2) -0.016(2) N3 0.047(3) 0.033(2) 0.031(2) 0.003(2) -0.008(2) -0.024(2) N4 0.042(2) 0.032(2) 0.026(2) 0.003(2) -0.009(2) -0.020(2) N5 0.037(2) 0.032(2) 0.026(2) 0.002(2) -0.008(2) -0.017(2) N6 0.050(3) 0.041(3) 0.036(2) 0.004(2) -0.018(2) -0.019(2) C1 0.062(4) 0.052(4) 0.046(3) -0.006(3) -0.012(3) -0.029(3) C2 0.074(5) 0.072(5) 0.049(4) -0.013(3) -0.015(3) -0.039(4) C3 0.072(5) 0.085(5) 0.037(3) -0.009(3) -0.019(3) -0.034(4) C4 0.060(4) 0.064(4) 0.034(3) 0.002(3) -0.019(3) -0.026(3) C5 0.036(3) 0.045(3) 0.030(3) 0.003(2) -0.009(2) -0.015(2) C6 0.038(3) 0.038(3) 0.031(2) 0.008(2) -0.009(2) -0.017(2) C7 0.034(2) 0.033(2) 0.028(2) -0.002(2) -0.003(2) -0.017(2) C8 0.038(3) 0.041(3) 0.034(3) 0.000(2) -0.007(2) -0.022(2) C9 0.038(3) 0.037(3) 0.032(3) 0.001(2) -0.009(2) -0.016(2) C10 0.057(4) 0.048(3) 0.039(3) 0.009(3) -0.010(3) -0.027(3) C11 0.066(4) 0.055(4) 0.044(3) 0.012(3) -0.012(3) -0.026(3) C12 0.071(5) 0.068(4) 0.043(3) 0.012(3) -0.025(3) -0.026(4) C13 0.064(4) 0.060(4) 0.048(4) 0.007(3) -0.032(3) -0.024(3) O1 0.049(2) 0.041(2) 0.059(3) 0.000(2) 0.001(2) -0.021(2) O2 0.067(3) 0.047(3) 0.064(3) -0.003(2) 0.012(2) -0.034(2) C14 0.044(3) 0.035(3) 0.037(3) 0.004(2) -0.005(2) -0.017(2) C15 0.075(6) 0.053(5) 0.104(7) -0.018(5) 0.024(5) -0.025(4) F1 0.061(15) 0.103(21) 0.258(43) -0.068(24) -0.062(20) 0.008(13) F2 0.116(15) 0.061(11) 0.052(12) -0.032(9) 0.002(10) -0.022(9) F3 0.138(26) 0.119(20) 0.172(31) -0.087(19) 0.101(24) -0.093(20) F1A 0.154(22) 0.279(50) 0.107(26) -0.142(30) 0.046(19) -0.109(30) F2A 0.051(12) 0.119(20) 0.182(31) -0.079(21) 0.043(16) -0.040(12) F3A 0.085(18) 0.055(11) 0.151(26) -0.003(13) 0.002(16) 0.017(12) F1B 0.122(23) 0.062(12) 0.101(24) -0.008(15) -0.022(17) 0.008(13) F2B 0.168(33) 0.106(20) 0.092(17) -0.047(15) 0.070(21) -0.070(20) F3B 0.056(16) 0.169(44) 0.298(71) -0.053(40) -0.025(29) 0.015(25) O3 0.053(2) 0.050(2) 0.040(2) 0.008(2) -0.012(2) -0.034(2) O4 0.056(3) 0.087(4) 0.093(4) 0.023(3) -0.016(3) -0.019(3) C16 0.053(4) 0.053(3) 0.038(3) -0.002(3) -0.008(3) -0.032(3) C17 0.068(5) 0.088(6) 0.073(5) -0.014(4) 0.009(4) -0.055(5) O5 0.042(2) 0.047(2) 0.056(3) -0.004(2) -0.020(2) -0.019(2) O6 0.060(3) 0.046(2) 0.041(2) -0.004(2) -0.003(2) -0.024(2) C18 0.038(3) 0.052(3) 0.031(3) -0.009(2) -0.003(2) -0.019(3) C19 0.067(5) 0.076(5) 0.085(6) -0.006(4) -0.031(4) -0.040(4) _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 O3 1.937(4) . ? Cu1 N2 1.958(4) . ? Cu1 N1 2.038(5) . ? Cu1 N4 2.045(4) . ? Cu1 O1 2.220(4) . ? Cu2 O5 1.924(4) 2_466 ? Cu2 N5 1.970(4) . ? Cu2 N6 2.029(5) . ? Cu2 S1 2.2924(15) . ? Cu2 O6 2.349(4) . ? S1 C7 1.715(5) . ? N1 C1 1.336(8) . ? N1 C5 1.354(7) . ? N2 C6 1.279(7) . ? N2 N3 1.360(6) . ? N3 C7 1.358(6) . ? N4 C7 1.340(6) . ? N4 N5 1.369(6) . ? N5 C8 1.279(7) . ? N6 C13 1.341(8) . ? N6 C9 1.350(7) . ? C1 C2 1.385(9) . ? C2 C3 1.378(11) . ? C3 C4 1.378(10) . ? C4 C5 1.390(8) . ? C5 C6 1.459(8) . ? C8 C9 1.458(7) . ? C9 C10 1.377(8) . ? C10 C11 1.385(9) . ? C11 C12 1.380(10) . ? C12 C13 1.378(10) . ? O1 C14 1.240(6) . ? O2 C14 1.225(7) . ? C14 C15 1.535(6) . ? C15 F1A 1.335(5) . ? C15 F3B 1.335(5) . ? C15 F3 1.336(5) . ? C15 F1B 1.336(5) . ? C15 F2 1.337(5) . ? C15 F3A 1.337(5) . ? C15 F1 1.339(5) . ? C15 F2A 1.339(5) . ? C15 F2B 1.340(5) . ? O3 C16 1.262(7) . ? O4 C16 1.208(8) . ? C16 C17 1.537(6) . ? C17 F5 1.327(5) . ? C17 F5A 1.331(5) . ? C17 F4A 1.332(4) . ? C17 F5B 1.334(5) . ? C17 F4 1.335(4) . ? C17 F4B 1.337(5) . ? C17 F6B 1.340(5) . ? C17 F6 1.346(5) . ? C17 F6A 1.349(5) . ? O5 C18 1.237(6) . ? O5 Cu2 1.924(4) 2_466 ? O6 C18 1.229(7) . ? C18 C19 1.534(6) . ? C19 F9 1.315(5) . ? C19 F9A 1.322(5) . ? C19 F9B 1.326(5) . ? C19 F7A 1.335(5) . ? C19 F7B 1.339(5) . ? C19 F7 1.347(4) . ? C19 F8 1.351(4) . ? C19 F8B 1.352(5) . ? C19 F8A 1.359(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 O3 Cu1 N2 166.5(2) . . ? O3 Cu1 N1 99.7(2) . . ? N2 Cu1 N1 79.3(2) . . ? O3 Cu1 N4 102.0(2) . . ? N2 Cu1 N4 77.8(2) . . ? N1 Cu1 N4 157.0(2) . . ? O3 Cu1 O1 91.6(2) . . ? N2 Cu1 O1 101.8(2) . . ? N1 Cu1 O1 92.5(2) . . ? N4 Cu1 O1 94.5(2) . . ? O5 Cu2 N5 156.4(2) 2_466 . ? O5 Cu2 N6 90.7(2) 2_466 . ? N5 Cu2 N6 80.5(2) . . ? O5 Cu2 S1 103.42(14) 2_466 . ? N5 Cu2 S1 84.53(12) . . ? N6 Cu2 S1 165.04(14) . . ? O5 Cu2 O6 96.6(2) 2_466 . ? N5 Cu2 O6 105.0(2) . . ? N6 Cu2 O6 88.7(2) . . ? S1 Cu2 O6 94.54(11) . . ? C7 S1 Cu2 94.3(2) . . ? C1 N1 C5 119.1(5) . . ? C1 N1 Cu1 128.1(4) . . ? C5 N1 Cu1 112.4(4) . . ? C6 N2 N3 123.8(4) . . ? C6 N2 Cu1 119.0(4) . . ? N3 N2 Cu1 116.7(3) . . ? C7 N3 N2 114.7(4) . . ? C7 N4 N5 112.1(4) . . ? C7 N4 Cu1 113.3(3) . . ? N5 N4 Cu1 132.2(3) . . ? C8 N5 N4 121.1(4) . . ? C8 N5 Cu2 116.3(4) . . ? N4 N5 Cu2 122.6(3) . . ? C13 N6 C9 118.5(5) . . ? C13 N6 Cu2 129.1(4) . . ? C9 N6 Cu2 112.3(3) . . ? N1 C1 C2 122.1(6) . . ? C3 C2 C1 118.7(6) . . ? C2 C3 C4 120.1(6) . . ? C3 C4 C5 118.3(6) . . ? N1 C5 C4 121.7(6) . . ? N1 C5 C6 115.1(5) . . ? C4 C5 C6 123.1(5) . . ? N2 C6 C5 113.9(5) . . ? N4 C7 N3 115.4(4) . . ? N4 C7 S1 126.5(4) . . ? N3 C7 S1 118.1(4) . . ? N5 C8 C9 116.1(5) . . ? N6 C9 C10 122.1(5) . . ? N6 C9 C8 114.5(5) . . ? C10 C9 C8 123.3(5) . . ? C9 C10 C11 119.1(6) . . ? C12 C11 C10 118.9(6) . . ? C13 C12 C11 119.2(6) . . ? N6 C13 C12 122.3(6) . . ? C14 O1 Cu1 119.9(3) . . ? O2 C14 O1 129.8(5) . . ? O2 C14 C15 115.2(4) . . ? O1 C14 C15 115.0(4) . . ? F3B C15 F1B 107.6(4) . . ? F3 C15 F2 107.4(4) . . ? F1A C15 F3A 107.5(4) . . ? F3 C15 F1 107.3(4) . . ? F2 C15 F1 107.1(4) . . ? F1A C15 F2A 107.4(4) . . ? F3A C15 F2A 107.1(4) . . ? F3B C15 F2B 107.3(4) . . ? F1B C15 F2B 107.1(4) . . ? F1A C15 C14 111.7(4) . . ? F3B C15 C14 111.7(4) . . ? F3 C15 C14 111.7(4) . . ? F1B C15 C14 111.6(4) . . ? F2 C15 C14 111.7(4) . . ? F3A C15 C14 111.5(4) . . ? F1 C15 C14 111.4(4) . . ? F2A C15 C14 111.4(4) . . ? F2B C15 C14 111.3(4) . . ? C16 O3 Cu1 121.3(4) . . ? O4 C16 O3 128.9(5) . . ? O4 C16 C17 117.8(5) . . ? O3 C16 C17 113.3(4) . . ? F5A C17 F4A 107.9(4) . . ? F5 C17 F4 108.1(4) . . ? F5B C17 F4B 107.5(4) . . ? F5B C17 F6B 107.3(4) . . ? F4B C17 F6B 107.1(4) . . ? F5 C17 F6 107.3(4) . . ? F4 C17 F6 107.1(4) . . ? F5A C17 F6A 106.9(4) . . ? F4A C17 F6A 106.8(4) . . ? F5 C17 C16 112.3(4) . . ? F5A C17 C16 112.6(4) . . ? F4A C17 C16 112.3(4) . . ? F5B C17 C16 112.0(4) . . ? F4 C17 C16 111.4(4) . . ? F4B C17 C16 111.5(4) . . ? F6B C17 C16 111.2(4) . . ? F6 C17 C16 110.4(4) . . ? F6A C17 C16 110.1(4) . . ? C18 O5 Cu2 129.2(4) . 2_466 ? C18 O6 Cu2 120.3(3) . . ? O6 C18 O5 131.0(5) . . ? O6 C18 C19 115.0(4) . . ? O5 C18 C19 113.9(4) . . ? F9A C19 F7A 108.9(4) . . ? F9B C19 F7B 108.1(4) . . ? F9 C19 F7 108.6(4) . . ? F9 C19 F8 108.3(4) . . ? F7 C19 F8 105.3(4) . . ? F9B C19 F8B 107.2(4) . . ? F7B C19 F8B 106.0(4) . . ? F9A C19 F8A 107.1(4) . . ? F7A C19 F8A 105.9(4) . . ? F9 C19 C18 113.7(4) . . ? F9A C19 C18 113.0(4) . . ? F9B C19 C18 112.8(4) . . ? F7A C19 C18 111.8(4) . . ? F7B C19 C18 111.6(4) . . ? F7 C19 C18 110.7(4) . . ? F8 C19 C18 109.9(4) . . ? F8B C19 C18 110.8(4) . . ? F8A C19 C18 109.9(4) . . ? #====END #compound 15 in the Text data_jdr6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Cu N9 O9 S' _chemical_formula_weight 534.92 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' '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 'P2(1)/c' 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 8.2376(1) _cell_length_b 18.0917(1) _cell_length_c 13.2848(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.604(1) _cell_angle_gamma 90.00 _cell_volume 1970.40(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'long rods' _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.287 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.7025 _exptl_absorpt_correction_T_max 0.8252 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD Diffractometer' _diffrn_measurement_method '\w-scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12952 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.35 _reflns_number_total 4935 _reflns_number_gt 3879 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _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^)+(0.0464P)^2^+1.5579P] 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 0.0009(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4935 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.03157(4) 0.635478(15) 0.66060(2) 0.03485(11) Uani 1 1 d . . . S1 S 0.14542(8) 0.52764(3) 0.61218(5) 0.03694(15) Uani 1 1 d . A . N1 N 0.0062(3) 0.74275(11) 0.69598(16) 0.0377(5) Uani 1 1 d . A . C1 C 0.0766(3) 0.78849(13) 0.63204(19) 0.0359(5) Uani 1 1 d . . . C2 C 0.0759(4) 0.86412(13) 0.6436(2) 0.0435(6) Uani 1 1 d . A . H2 H 0.1221 0.8947 0.5979 0.052 Uiso 1 1 calc R . . C3 C 0.0046(4) 0.89354(14) 0.7249(2) 0.0483(7) Uani 1 1 d . . . H3 H 0.0048 0.9444 0.7354 0.058 Uiso 1 1 calc R A . C4 C -0.0667(4) 0.84716(15) 0.7900(2) 0.0478(7) Uani 1 1 d . A . H4 H -0.1148 0.8662 0.8450 0.057 Uiso 1 1 calc R . . C5 C -0.0654(4) 0.77189(14) 0.7723(2) 0.0439(6) Uani 1 1 d . . . H5 H -0.1161 0.7406 0.8152 0.053 Uiso 1 1 calc R A . N2 N 0.1577(2) 0.68063(10) 0.55907(15) 0.0321(4) Uani 1 1 d . A . C6 C 0.1582(3) 0.75117(13) 0.55330(19) 0.0380(5) Uani 1 1 d . A . H6 H 0.2065 0.7766 0.5032 0.046 Uiso 1 1 calc R . . N3 N 0.2285(2) 0.63714(10) 0.49164(15) 0.0332(4) Uani 1 1 d . . . H3A H 0.2708 0.6552 0.4403 0.040 Uiso 1 1 calc R A . C7 C 0.2279(3) 0.56420(12) 0.51079(17) 0.0304(5) Uani 1 1 d . A . N4 N 0.2958(3) 0.51881(10) 0.44770(16) 0.0360(4) Uani 1 1 d . . . H4A H 0.2961 0.4718 0.4569 0.043 Uiso 1 1 calc R A . N5 N 0.3650(2) 0.54951(11) 0.36766(15) 0.0343(4) Uani 1 1 d . A . C8 C 0.4295(3) 0.50513(13) 0.30886(19) 0.0353(5) Uani 1 1 d . . . H8 H 0.4288 0.4544 0.3197 0.042 Uiso 1 1 calc R A . C9 C 0.5048(3) 0.53707(13) 0.22352(18) 0.0338(5) Uani 1 1 d . A . C10 C 0.5842(3) 0.49443(14) 0.15780(19) 0.0398(6) Uani 1 1 d . . . H10 H 0.5912 0.4435 0.1663 0.048 Uiso 1 1 calc R A . C11 C 0.6536(4) 0.52832(16) 0.0790(2) 0.0461(6) Uani 1 1 d . A . H11 H 0.7095 0.5001 0.0351 0.055 Uiso 1 1 calc R . . C12 C 0.6403(4) 0.60351(17) 0.0654(2) 0.0486(7) Uani 1 1 d . . . H12 H 0.6847 0.6263 0.0116 0.058 Uiso 1 1 calc R A . C13 C 0.5608(4) 0.64439(15) 0.1320(2) 0.0454(6) Uani 1 1 d . A . H13 H 0.5512 0.6953 0.1238 0.055 Uiso 1 1 calc R . . N6 N 0.4965(3) 0.61110(11) 0.20932(16) 0.0378(5) Uani 1 1 d . . . H6A H 0.4484 0.6377 0.2511 0.045 Uiso 1 1 calc R A . N7 N -0.0543(3) 0.58368(13) 0.8397(2) 0.0493(6) Uani 1 1 d . . . O1 O -0.1104(3) 0.58863(12) 0.75113(18) 0.0573(5) Uani 1 1 d . A . O2 O -0.1324(5) 0.54709(17) 0.8990(2) 0.1069(12) Uani 1 1 d . A . O3 O 0.0757(4) 0.61224(19) 0.8691(2) 0.0953(9) Uani 1 1 d . A . N8 N -0.2928(3) 0.67544(13) 0.52365(19) 0.0472(6) Uani 1 1 d . . . O4 O -0.1913(3) 0.62375(12) 0.5347(3) 0.0430(7) Uani 0.856(7) 1 d P A . O5 O -0.2485(4) 0.73590(12) 0.4953(2) 0.0803(8) Uani 1 1 d . A . O6 O -0.4322(3) 0.6649(2) 0.5502(3) 0.0849(13) Uani 0.856(7) 1 d P A . O4A O -0.217(2) 0.6294(9) 0.5775(14) 0.042(4) Uiso 0.144(7) 1 d P A 1 O6A O -0.380(3) 0.6439(13) 0.4469(19) 0.100(9) Uiso 0.144(7) 1 d P A 1 N9 N 0.4092(3) 0.77433(13) 0.33048(19) 0.0510(6) Uani 1 1 d . . . O7 O 0.4675(17) 0.7957(3) 0.2540(5) 0.117(4) Uani 0.86(2) 1 d P B . O8 O 0.3544(3) 0.70895(10) 0.33148(16) 0.0535(5) Uani 1 1 d . B . O9 O 0.3999(9) 0.81562(17) 0.4035(5) 0.0572(13) Uani 0.86(2) 1 d P B . O7A O 0.545(2) 0.7803(12) 0.291(2) 0.044(7) Uiso 0.14(2) 1 d P B 2 O9A O 0.346(3) 0.8169(11) 0.373(2) 0.040(5) Uiso 0.14(2) 1 d P B 2 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 0.04179(18) 0.02482(15) 0.04013(18) 0.00009(11) 0.01506(12) -0.00271(11) S1 0.0484(4) 0.0261(3) 0.0386(3) 0.0049(2) 0.0156(3) 0.0018(2) N1 0.0454(12) 0.0263(9) 0.0431(11) -0.0025(8) 0.0133(9) -0.0018(8) C1 0.0416(13) 0.0274(11) 0.0399(13) -0.0022(9) 0.0089(10) -0.0031(9) C2 0.0566(16) 0.0258(12) 0.0498(15) 0.0001(10) 0.0130(12) -0.0013(11) C3 0.0629(18) 0.0270(12) 0.0559(17) -0.0062(11) 0.0104(14) 0.0035(12) C4 0.0605(18) 0.0358(13) 0.0494(16) -0.0081(11) 0.0172(13) 0.0066(12) C5 0.0545(16) 0.0342(13) 0.0455(15) -0.0005(11) 0.0179(12) 0.0024(11) N2 0.0358(10) 0.0252(9) 0.0364(10) -0.0017(7) 0.0088(8) -0.0020(7) C6 0.0476(14) 0.0284(11) 0.0398(13) -0.0008(10) 0.0131(11) -0.0052(10) N3 0.0401(11) 0.0258(9) 0.0358(10) -0.0014(8) 0.0146(8) -0.0027(8) C7 0.0309(11) 0.0272(10) 0.0338(11) -0.0002(9) 0.0062(9) -0.0025(8) N4 0.0464(12) 0.0228(9) 0.0414(11) 0.0009(8) 0.0173(9) 0.0001(8) N5 0.0392(11) 0.0285(9) 0.0369(11) 0.0010(8) 0.0127(8) -0.0013(8) C8 0.0415(13) 0.0269(11) 0.0384(12) -0.0010(9) 0.0080(10) -0.0026(9) C9 0.0365(12) 0.0312(11) 0.0340(12) -0.0008(9) 0.0046(10) -0.0014(9) C10 0.0470(14) 0.0341(12) 0.0390(13) -0.0029(10) 0.0069(11) 0.0037(10) C11 0.0531(16) 0.0510(16) 0.0360(13) -0.0044(11) 0.0135(12) 0.0018(12) C12 0.0586(18) 0.0504(16) 0.0386(14) 0.0069(12) 0.0142(13) -0.0027(13) C13 0.0543(16) 0.0375(14) 0.0452(15) 0.0071(11) 0.0081(12) -0.0018(11) N6 0.0446(12) 0.0302(10) 0.0396(11) -0.0005(8) 0.0096(9) -0.0004(9) N7 0.0692(17) 0.0310(11) 0.0510(15) -0.0014(10) 0.0230(13) 0.0071(11) O1 0.0606(13) 0.0519(12) 0.0627(14) 0.0021(10) 0.0232(11) -0.0128(10) O2 0.165(3) 0.083(2) 0.087(2) 0.0225(16) 0.083(2) 0.002(2) O3 0.111(3) 0.104(2) 0.0678(18) 0.0121(17) -0.0037(17) 0.002(2) N8 0.0486(14) 0.0372(12) 0.0538(14) -0.0005(10) -0.0047(11) 0.0003(10) O4 0.0448(13) 0.0271(11) 0.0573(18) -0.0036(10) 0.0068(12) 0.0032(8) O5 0.0961(19) 0.0325(11) 0.112(2) 0.0130(12) 0.0106(17) 0.0020(11) O6 0.0440(17) 0.102(3) 0.112(3) 0.019(2) 0.0237(16) 0.0093(16) N9 0.0715(17) 0.0315(11) 0.0519(14) 0.0014(10) 0.0162(12) -0.0049(11) O7 0.222(10) 0.063(2) 0.076(3) 0.004(2) 0.070(5) -0.049(3) O8 0.0819(15) 0.0277(9) 0.0539(12) -0.0012(8) 0.0218(11) -0.0102(9) O9 0.072(3) 0.0385(14) 0.062(2) -0.0138(13) 0.012(2) -0.0109(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 O1 1.951(2) . ? Cu1 N2 1.9594(19) . ? Cu1 N1 2.013(2) . ? Cu1 O4A 2.230(16) . ? Cu1 S1 2.2842(6) . ? Cu1 O4 2.369(3) . ? S1 C7 1.701(2) . ? N1 C5 1.331(3) . ? N1 C1 1.356(3) . ? C1 C2 1.377(3) . ? C1 C6 1.463(3) . ? C2 C3 1.385(4) . ? C3 C4 1.377(4) . ? C4 C5 1.382(4) . ? N2 C6 1.278(3) . ? N2 N3 1.365(3) . ? N3 C7 1.344(3) . ? C7 N4 1.335(3) . ? N4 N5 1.372(3) . ? N5 C8 1.272(3) . ? C8 C9 1.463(3) . ? C9 N6 1.353(3) . ? C9 C10 1.377(3) . ? C10 C11 1.384(4) . ? C11 C12 1.375(4) . ? C12 C13 1.368(4) . ? C13 N6 1.343(3) . ? N7 O3 1.218(4) . ? N7 O1 1.224(3) . ? N7 O2 1.254(3) . ? N8 O5 1.224(3) . ? N8 O4A 1.229(16) . ? N8 O6 1.248(4) . ? N8 O4 1.254(3) . ? N8 O6A 1.32(2) . ? O4 O4A 0.633(17) . ? O6 O6A 1.52(3) . ? N9 O9A 1.12(2) . ? N9 O7 1.228(4) . ? N9 O9 1.233(4) . ? N9 O8 1.266(3) . ? N9 O7A 1.28(2) . ? O7 O7A 0.818(15) . ? O9 O9A 0.57(2) . ? 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 174.47(10) . . ? O1 Cu1 N1 101.11(9) . . ? N2 Cu1 N1 80.39(8) . . ? O1 Cu1 O4A 73.0(5) . . ? N2 Cu1 O4A 101.7(5) . . ? N1 Cu1 O4A 93.0(5) . . ? O1 Cu1 S1 95.15(7) . . ? N2 Cu1 S1 84.40(6) . . ? N1 Cu1 S1 160.79(7) . . ? O4A Cu1 S1 101.6(5) . . ? O1 Cu1 O4 85.78(11) . . ? N2 Cu1 O4 88.73(10) . . ? N1 Cu1 O4 99.21(9) . . ? O4A Cu1 O4 15.5(5) . . ? S1 Cu1 O4 92.06(7) . . ? C7 S1 Cu1 95.60(8) . . ? C5 N1 C1 118.9(2) . . ? C5 N1 Cu1 128.61(18) . . ? C1 N1 Cu1 112.43(16) . . ? N1 C1 C2 122.0(2) . . ? N1 C1 C6 114.9(2) . . ? C2 C1 C6 123.1(2) . . ? C1 C2 C3 118.4(3) . . ? C4 C3 C2 119.7(2) . . ? C3 C4 C5 118.9(3) . . ? N1 C5 C4 122.1(3) . . ? C6 N2 N3 122.1(2) . . ? C6 N2 Cu1 117.55(17) . . ? N3 N2 Cu1 120.05(14) . . ? N2 C6 C1 114.4(2) . . ? C7 N3 N2 115.58(19) . . ? N4 C7 N3 118.4(2) . . ? N4 C7 S1 118.83(17) . . ? N3 C7 S1 122.76(17) . . ? C7 N4 N5 117.96(19) . . ? C8 N5 N4 116.8(2) . . ? N5 C8 C9 117.4(2) . . ? N6 C9 C10 119.1(2) . . ? N6 C9 C8 118.6(2) . . ? C10 C9 C8 122.2(2) . . ? C9 C10 C11 119.2(2) . . ? C12 C11 C10 120.3(3) . . ? C13 C12 C11 119.1(3) . . ? N6 C13 C12 120.1(3) . . ? C13 N6 C9 122.1(2) . . ? O3 N7 O1 121.0(3) . . ? O3 N7 O2 120.7(3) . . ? O1 N7 O2 118.3(3) . . ? N7 O1 Cu1 115.54(19) . . ? O5 N8 O4A 129.3(8) . . ? O5 N8 O6 122.3(3) . . ? O4A N8 O6 99.4(9) . . ? O5 N8 O4 119.1(3) . . ? O4A N8 O4 29.5(8) . . ? O6 N8 O4 118.3(3) . . ? O5 N8 O6A 107.9(11) . . ? O4A N8 O6A 111.5(13) . . ? O6 N8 O6A 72.7(11) . . ? O4 N8 O6A 94.4(10) . . ? O4A O4 N8 73.1(15) . . ? O4A O4 Cu1 69.7(15) . . ? N8 O4 Cu1 118.6(2) . . ? N8 O6 O6A 55.8(9) . . ? O4 O4A N8 77.4(16) . . ? O4 O4A Cu1 94.8(17) . . ? N8 O4A Cu1 130.3(11) . . ? N8 O6A O6 51.5(9) . . ? O9A N9 O7 116.3(10) . . ? O9A N9 O9 27.7(12) . . ? O7 N9 O9 121.3(3) . . ? O9A N9 O8 117.0(12) . . ? O7 N9 O8 118.1(3) . . ? O9 N9 O8 120.5(3) . . ? O9A N9 O7A 128.2(16) . . ? O7 N9 O7A 37.9(7) . . ? O9 N9 O7A 113.1(8) . . ? O8 N9 O7A 114.1(9) . . ? O7A O7 N9 74.7(15) . . ? O9A O9 N9 65(2) . . ? O7 O7A N9 67.4(13) . . ? O9 O9A N9 88(2) . . ? 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 O1 Cu1 S1 C7 165.18(11) . . . . ? N2 Cu1 S1 C7 -9.29(10) . . . . ? N1 Cu1 S1 C7 -46.9(2) . . . . ? O4A Cu1 S1 C7 91.5(5) . . . . ? O4 Cu1 S1 C7 79.23(11) . . . . ? O1 Cu1 N1 C5 10.2(3) . . . . ? N2 Cu1 N1 C5 -175.2(3) . . . . ? O4A Cu1 N1 C5 83.5(5) . . . . ? S1 Cu1 N1 C5 -137.1(2) . . . . ? O4 Cu1 N1 C5 97.7(3) . . . . ? O1 Cu1 N1 C1 -171.23(18) . . . . ? N2 Cu1 N1 C1 3.36(18) . . . . ? O4A Cu1 N1 C1 -98.0(5) . . . . ? S1 Cu1 N1 C1 41.4(3) . . . . ? O4 Cu1 N1 C1 -83.8(2) . . . . ? C5 N1 C1 C2 -0.2(4) . . . . ? Cu1 N1 C1 C2 -178.9(2) . . . . ? C5 N1 C1 C6 177.4(2) . . . . ? Cu1 N1 C1 C6 -1.3(3) . . . . ? N1 C1 C2 C3 1.8(4) . . . . ? C6 C1 C2 C3 -175.6(3) . . . . ? C1 C2 C3 C4 -1.6(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C1 N1 C5 C4 -1.6(4) . . . . ? Cu1 N1 C5 C4 176.8(2) . . . . ? C3 C4 C5 N1 1.8(5) . . . . ? O1 Cu1 N2 C6 100.8(9) . . . . ? N1 Cu1 N2 C6 -5.4(2) . . . . ? O4A Cu1 N2 C6 85.7(5) . . . . ? S1 Cu1 N2 C6 -173.7(2) . . . . ? O4 Cu1 N2 C6 94.2(2) . . . . ? O1 Cu1 N2 N3 -73.3(9) . . . . ? N1 Cu1 N2 N3 -179.44(19) . . . . ? O4A Cu1 N2 N3 -88.4(5) . . . . ? S1 Cu1 N2 N3 12.32(16) . . . . ? O4 Cu1 N2 N3 -79.87(18) . . . . ? N3 N2 C6 C1 -180.0(2) . . . . ? Cu1 N2 C6 C1 6.1(3) . . . . ? N1 C1 C6 N2 -3.0(3) . . . . ? C2 C1 C6 N2 174.5(3) . . . . ? C6 N2 N3 C7 175.9(2) . . . . ? Cu1 N2 N3 C7 -10.4(3) . . . . ? N2 N3 C7 N4 -179.8(2) . . . . ? N2 N3 C7 S1 -0.2(3) . . . . ? Cu1 S1 C7 N4 -172.40(18) . . . . ? Cu1 S1 C7 N3 8.0(2) . . . . ? N3 C7 N4 N5 1.1(3) . . . . ? S1 C7 N4 N5 -178.52(17) . . . . ? C7 N4 N5 C8 179.7(2) . . . . ? N4 N5 C8 C9 -179.6(2) . . . . ? N5 C8 C9 N6 -2.6(4) . . . . ? N5 C8 C9 C10 177.1(2) . . . . ? N6 C9 C10 C11 0.1(4) . . . . ? C8 C9 C10 C11 -179.6(2) . . . . ? C9 C10 C11 C12 -1.3(4) . . . . ? C10 C11 C12 C13 1.4(5) . . . . ? C11 C12 C13 N6 -0.2(5) . . . . ? C12 C13 N6 C9 -1.1(4) . . . . ? C10 C9 N6 C13 1.2(4) . . . . ? C8 C9 N6 C13 -179.1(2) . . . . ? O3 N7 O1 Cu1 6.1(4) . . . . ? O2 N7 O1 Cu1 -172.4(2) . . . . ? N2 Cu1 O1 N7 178(22) . . . . ? N1 Cu1 O1 N7 -77.0(2) . . . . ? O4A Cu1 O1 N7 -166.7(5) . . . . ? S1 Cu1 O1 N7 92.71(19) . . . . ? O4 Cu1 O1 N7 -175.6(2) . . . . ? O5 N8 O4 O4A 119.2(16) . . . . ? O6 N8 O4 O4A -54.8(16) . . . . ? O6A N8 O4 O4A -127.6(19) . . . . ? O5 N8 O4 Cu1 64.5(4) . . . . ? O4A N8 O4 Cu1 -54.7(16) . . . . ? O6 N8 O4 Cu1 -109.5(3) . . . . ? O6A N8 O4 Cu1 177.8(11) . . . . ? O1 Cu1 O4 O4A 33.6(16) . . . . ? N2 Cu1 O4 O4A -147.1(16) . . . . ? N1 Cu1 O4 O4A -67.0(16) . . . . ? S1 Cu1 O4 O4A 128.6(16) . . . . ? O1 Cu1 O4 N8 89.9(3) . . . . ? N2 Cu1 O4 N8 -90.7(3) . . . . ? N1 Cu1 O4 N8 -10.7(3) . . . . ? O4A Cu1 O4 N8 56.3(16) . . . . ? S1 Cu1 O4 N8 -175.1(3) . . . . ? O5 N8 O6 O6A 100.6(11) . . . . ? O4A N8 O6 O6A -109.7(14) . . . . ? O4 N8 O6 O6A -85.6(11) . . . . ? Cu1 O4 O4A N8 130.2(9) . . . . ? N8 O4 O4A Cu1 -130.2(9) . . . . ? O5 N8 O4A O4 -80.3(17) . . . . ? O6 N8 O4A O4 133.2(13) . . . . ? O6A N8 O4A O4 58.1(19) . . . . ? O5 N8 O4A Cu1 5(2) . . . . ? O6 N8 O4A Cu1 -141.2(14) . . . . ? O4 N8 O4A Cu1 86(2) . . . . ? O6A N8 O4A Cu1 143.8(17) . . . . ? O1 Cu1 O4A O4 -144.8(17) . . . . ? N2 Cu1 O4A O4 33.7(17) . . . . ? N1 Cu1 O4A O4 114.5(16) . . . . ? S1 Cu1 O4A O4 -52.9(16) . . . . ? O1 Cu1 O4A N8 137.7(18) . . . . ? N2 Cu1 O4A N8 -43.8(18) . . . . ? N1 Cu1 O4A N8 37.0(17) . . . . ? S1 Cu1 O4A N8 -130.4(16) . . . . ? O4 Cu1 O4A N8 -78(2) . . . . ? O5 N8 O6A O6 -119.2(5) . . . . ? O4A N8 O6A O6 93.5(11) . . . . ? O4 N8 O6A O6 118.3(4) . . . . ? O9A N9 O7 O7A 119(2) . . . . ? O9 N9 O7 O7A 88.0(15) . . . . ? O8 N9 O7 O7A -93.9(16) . . . . ? O7 N9 O9 O9A 87(3) . . . . ? O8 N9 O9 O9A -91(2) . . . . ? O7A N9 O9 O9A 129(3) . . . . ? O9A N9 O7A O7 -85(2) . . . . ? O9 N9 O7A O7 -111.9(11) . . . . ? O8 N9 O7A O7 105.4(13) . . . . ? O7 N9 O9A O9 -108(2) . . . . ? O8 N9 O9A O9 105(2) . . . . ? O7A N9 O9A O9 -65(3) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 29.35 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 1.473 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.063 #====END #compound 16 in the Text data_jdr2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H19 Cl3 Cu N6 O15 S' _chemical_formula_weight 701.29 _chemical_melting_point ? _chemical_compound_source 'see text' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4905(3) _cell_length_b 8.3949(3) _cell_length_c 21.9669(9) _cell_angle_alpha 98.635(1) _cell_angle_beta 90.821(1) _cell_angle_gamma 107.117(1) _cell_volume 1302.67(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'triclinic shaped blocks' _exptl_crystal_colour 'very dark green' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method ? _exptl_crystal_F_000 710 _exptl_absorpt_coefficient_mu 1.307 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 0.825 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD' _diffrn_measurement_method 'frames, \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8285 _diffrn_reflns_av_R_equivalents 0.0128 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 29.16 _reflns_number_total 5909 _reflns_number_observed 4908 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1996)' _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material 'SHELXTL (Siemens, 1996)' _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^)+(0.0709P)^2^+1.1038P] 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 5909 _refine_ls_number_parameters 382 _refine_ls_number_restraints 141 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.094 _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 0.19546(5) 0.43996(5) 0.146570(18) 0.04262(13) Uani 1 1 d . . . O13 O 0.2594(4) 0.2995(4) 0.07731(13) 0.0639(8) Uani 1 1 d D . . H13A H 0.191(5) 0.285(7) 0.0495(17) 0.080 Uiso 1 1 d D . . H13B H 0.358(4) 0.321(7) 0.065(2) 0.080 Uiso 1 1 d D . . C1 C -0.1583(4) 0.3632(4) 0.19578(16) 0.0426(7) Uani 1 1 d . . . C2 C -0.3441(5) 0.2882(5) 0.20738(19) 0.0543(9) Uani 1 1 d . . . H2 H -0.4015 0.3361 0.2393 0.065 Uiso 1 1 calc R . . C3 C -0.4413(6) 0.1371(5) 0.1688(2) 0.0645(11) Uani 1 1 d . . . H3 H -0.5661 0.0831 0.1744 0.077 Uiso 1 1 calc R . . C4 C -0.3511(6) 0.0704(5) 0.1230(2) 0.0665(11) Uani 1 1 d . . . H4 H -0.4144 -0.0298 0.0973 0.080 Uiso 1 1 calc R . . C5 C -0.1667(6) 0.1505(5) 0.11470(18) 0.0551(9) Uani 1 1 d . . . H5 H -0.1067 0.1020 0.0837 0.066 Uiso 1 1 calc R . . N1 N -0.0712(4) 0.2963(3) 0.14989(12) 0.0420(6) Uani 1 1 d . . . C6 C -0.0429(4) 0.5183(4) 0.23372(15) 0.0414(7) Uani 1 1 d . . . H6 H -0.0879 0.5747 0.2668 0.050 Uiso 1 1 calc R . . N2 N 0.1249(3) 0.5702(3) 0.21772(11) 0.0355(5) Uani 1 1 d . . . N3 N 0.2557(3) 0.7053(3) 0.25125(12) 0.0398(6) Uani 1 1 d . . . H3A H 0.2273 0.7670 0.2822 0.048 Uiso 1 1 calc R . . C7 C 0.4311(4) 0.7360(4) 0.23302(14) 0.0372(6) Uani 1 1 d . . . S1 S 0.48711(11) 0.62918(11) 0.16725(4) 0.0463(2) Uani 1 1 d . . . N4 N 0.5668(4) 0.8572(3) 0.26754(12) 0.0405(6) Uani 1 1 d . . . H4A H 0.6800 0.8841 0.2564 0.049 Uiso 1 1 calc R . . N5 N 0.5204(3) 0.9377(3) 0.32132(12) 0.0377(5) Uani 1 1 d . . . C8 C 0.6534(4) 1.0542(4) 0.35265(14) 0.0405(6) Uani 1 1 d . . . H8 H 0.7738 1.0831 0.3389 0.049 Uiso 1 1 calc R . . C9 C 0.6106(4) 1.1406(4) 0.41074(14) 0.0381(6) Uani 1 1 d . . . C10 C 0.3800(5) 1.1638(5) 0.48034(16) 0.0497(8) Uani 1 1 d . . . H10 H 0.2558 1.1271 0.4903 0.060 Uiso 1 1 calc R . . C11 C 0.5074(5) 1.2907(5) 0.51949(16) 0.0506(8) Uani 1 1 d . . . H11 H 0.4710 1.3403 0.5561 0.061 Uiso 1 1 calc R . . C12 C 0.6891(5) 1.3425(5) 0.50348(18) 0.0544(9) Uani 1 1 d . . . H12 H 0.7774 1.4280 0.5295 0.065 Uiso 1 1 calc R . . C13 C 0.7425(5) 1.2682(5) 0.44872(17) 0.0508(8) Uani 1 1 d . . . H13 H 0.8658 1.3040 0.4378 0.061 Uiso 1 1 calc R . . N6 N 0.4334(4) 1.0934(3) 0.42835(12) 0.0411(6) Uani 1 1 d . . . H6A H 0.3510 1.0138 0.4048 0.049 Uiso 1 1 calc R . . Cl1 Cl 0.95166(10) 1.77776(10) 0.39833(4) 0.04445(19) Uani 1 1 d D . . O1 O 1.1325(3) 1.7889(3) 0.37304(12) 0.0559(6) Uani 1 1 d D . . O2 O 0.9503(5) 1.9440(4) 0.42515(16) 0.0808(9) Uani 1 1 d D . . O3 O 0.9227(5) 1.6739(5) 0.44434(18) 0.0895(11) Uani 1 1 d D . . O4 O 0.8087(4) 1.7143(5) 0.35027(15) 0.0890(11) Uani 1 1 d D . . Cl2 Cl 0.23462(14) 0.30409(13) 0.31949(5) 0.0621(3) Uani 1 1 d D . . O5 O 0.0690(11) 0.3471(12) 0.3324(4) 0.070(2) Uiso 0.45 1 d PD . . O6 O 0.3885(15) 0.3964(14) 0.3596(5) 0.121(4) Uiso 0.45 1 d PD . . O7 O 0.2739(14) 0.3235(12) 0.2563(4) 0.093(3) Uiso 0.45 1 d PD . . O8 O 0.2015(12) 0.1225(8) 0.3211(4) 0.0663(19) Uiso 0.45 1 d PD . . O5A O 0.3649(18) 0.4567(15) 0.3094(7) 0.096(4) Uiso 0.30 1 d PD . . O6A O 0.271(2) 0.1478(14) 0.3045(6) 0.081(3) Uiso 0.30 1 d PD . . O7A O 0.0382(13) 0.2908(15) 0.3094(6) 0.068(3) Uiso 0.30 1 d PD . . O8A O 0.250(2) 0.338(2) 0.3890(5) 0.117(5) Uiso 0.30 1 d PD . . O5B O 0.143(2) 0.427(2) 0.3418(7) 0.091(5) Uiso 0.25 1 d PD . . O6B O 0.4330(15) 0.3697(18) 0.3377(7) 0.071(3) Uiso 0.25 1 d PD . . O7B O 0.2231(14) 0.2657(13) 0.2473(4) 0.039(2) Uiso 0.25 1 d PD . . O8B O 0.1507(19) 0.1496(15) 0.3419(7) 0.070(3) Uiso 0.25 1 d PD . . Cl3 Cl 1.07541(13) 0.76131(12) 0.06937(4) 0.0538(2) Uani 1 1 d D . . O9 O 1.1268(5) 0.8655(5) 0.12754(14) 0.0867(11) Uani 1 1 d D . . O10 O 0.9121(7) 0.7793(6) 0.0432(2) 0.130(2) Uani 1 1 d D . . O11 O 1.0551(7) 0.5894(4) 0.07260(18) 0.1024(14) Uani 1 1 d D . . O12 O 1.2239(8) 0.8161(6) 0.0303(2) 0.1275(18) Uani 1 1 d D . . O1S O -0.0736(4) -0.0860(5) 0.23495(16) 0.0852(12) Uani 1 1 d D . . H1S2 H -0.051(7) -0.097(6) 0.2012(12) 0.080 Uiso 1 1 d D . . H1S1 H 0.009(5) -0.017(5) 0.2525(19) 0.080 Uiso 1 1 d D . . O2S O 0.6042(6) 0.4033(6) 0.0439(2) 0.0979(13) Uani 1 1 d D . . H2S1 H 0.667(7) 0.488(4) 0.039(2) 0.080 Uiso 1 1 d D . . H2S2 H 0.614(8) 0.335(5) 0.019(2) 0.080 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 Cu1 0.0379(2) 0.0441(2) 0.0409(2) -0.00505(16) 0.00522(15) 0.01042(16) O13 0.0533(15) 0.0732(18) 0.0557(16) -0.0212(14) 0.0024(12) 0.0202(15) C1 0.0360(15) 0.0437(16) 0.0484(18) 0.0088(13) 0.0027(13) 0.0120(12) C2 0.0370(16) 0.058(2) 0.066(2) 0.0158(18) 0.0053(16) 0.0086(15) C3 0.0435(19) 0.056(2) 0.084(3) 0.020(2) -0.0037(19) -0.0028(16) C4 0.064(2) 0.049(2) 0.072(3) 0.0053(19) -0.013(2) -0.0031(18) C5 0.061(2) 0.0432(18) 0.054(2) 0.0003(15) -0.0054(17) 0.0084(16) N1 0.0415(14) 0.0405(13) 0.0416(14) 0.0044(11) -0.0010(11) 0.0101(11) C6 0.0371(15) 0.0476(17) 0.0398(16) 0.0037(13) 0.0055(12) 0.0150(13) N2 0.0326(12) 0.0375(12) 0.0351(12) 0.0021(10) 0.0012(9) 0.0106(10) N3 0.0338(12) 0.0440(14) 0.0377(13) -0.0041(10) 0.0047(10) 0.0107(10) C7 0.0365(14) 0.0400(15) 0.0353(14) 0.0044(11) 0.0054(11) 0.0126(12) S1 0.0393(4) 0.0515(4) 0.0410(4) -0.0054(3) 0.0117(3) 0.0086(3) N4 0.0309(12) 0.0485(14) 0.0371(13) -0.0016(11) 0.0066(10) 0.0082(10) N5 0.0337(12) 0.0426(13) 0.0350(12) 0.0005(10) 0.0059(10) 0.0114(10) C8 0.0344(14) 0.0444(16) 0.0398(16) 0.0035(12) 0.0063(12) 0.0089(12) C9 0.0356(14) 0.0389(15) 0.0398(15) 0.0050(12) 0.0038(12) 0.0116(12) C10 0.0401(17) 0.061(2) 0.0434(18) -0.0006(15) 0.0085(14) 0.0121(15) C11 0.0536(19) 0.0540(19) 0.0411(17) -0.0051(14) 0.0051(14) 0.0177(16) C12 0.051(2) 0.0490(19) 0.053(2) -0.0118(15) -0.0036(16) 0.0106(15) C13 0.0381(16) 0.0502(18) 0.055(2) -0.0043(15) 0.0068(14) 0.0049(14) N6 0.0333(12) 0.0467(14) 0.0381(13) -0.0019(11) 0.0032(10) 0.0080(10) Cl1 0.0365(4) 0.0543(4) 0.0393(4) 0.0036(3) 0.0094(3) 0.0103(3) O1 0.0411(13) 0.0679(16) 0.0516(14) 0.0009(12) 0.0158(11) 0.0091(11) O2 0.086(2) 0.0654(19) 0.089(2) -0.0038(16) 0.0279(18) 0.0254(17) O3 0.081(2) 0.109(3) 0.103(3) 0.064(2) 0.040(2) 0.042(2) O4 0.0532(17) 0.138(3) 0.0641(19) -0.022(2) -0.0050(14) 0.0301(19) Cl2 0.0512(5) 0.0597(5) 0.0800(7) 0.0267(5) 0.0040(4) 0.0159(4) Cl3 0.0577(5) 0.0629(5) 0.0391(4) -0.0002(4) 0.0025(3) 0.0198(4) O9 0.079(2) 0.104(3) 0.0548(18) -0.0199(17) 0.0019(15) 0.0088(19) O10 0.132(4) 0.147(4) 0.117(4) -0.047(3) -0.056(3) 0.090(3) O11 0.139(4) 0.066(2) 0.090(3) 0.0178(19) -0.040(2) 0.012(2) O12 0.161(5) 0.116(3) 0.095(3) 0.012(3) 0.072(3) 0.025(3) O1S 0.0472(16) 0.112(3) 0.069(2) -0.0210(19) 0.0210(15) -0.0009(16) O2S 0.081(3) 0.097(3) 0.113(3) 0.005(3) 0.043(2) 0.026(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 O13 1.936(3) . ? Cu1 N2 1.941(2) . ? Cu1 N1 2.016(3) . ? Cu1 S1 2.2835(9) . ? Cu1 O11 2.581(4) 1_455 ? Cu1 O7 2.850(8) . ? O13 H13A 0.76(2) . ? O13 H13B 0.77(2) . ? C1 N1 1.350(4) . ? C1 C2 1.393(5) . ? C1 C6 1.458(5) . ? C2 C3 1.405(6) . ? C2 H2 0.9300 . ? C3 C4 1.361(7) . ? C3 H3 0.9300 . ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 N1 1.339(4) . ? C5 H5 0.9300 . ? C6 N2 1.277(4) . ? C6 H6 0.9300 . ? N2 N3 1.365(3) . ? N3 C7 1.342(4) . ? N3 H3A 0.8600 . ? C7 N4 1.334(4) . ? C7 S1 1.708(3) . ? N4 N5 1.372(3) . ? N4 H4A 0.8600 . ? N5 C8 1.275(4) . ? C8 C9 1.459(4) . ? C8 H8 0.9300 . ? C9 N6 1.349(4) . ? C9 C13 1.380(5) . ? C10 N6 1.328(4) . ? C10 C11 1.374(5) . ? C10 H10 0.9300 . ? C11 C12 1.370(5) . ? C11 H11 0.9300 . ? C12 C13 1.390(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? N6 H6A 0.8600 . ? Cl1 O3 1.410(3) . ? Cl1 O4 1.417(3) . ? Cl1 O2 1.434(3) . ? Cl1 O1 1.454(2) . ? Cl2 O6 1.395(9) . ? Cl2 O6A 1.411(10) . ? Cl2 O5 1.411(7) . ? Cl2 O5A 1.413(11) . ? Cl2 O8B 1.429(10) . ? Cl2 O5B 1.433(12) . ? Cl2 O7 1.445(8) . ? Cl2 O6B 1.451(11) . ? Cl2 O7A 1.454(9) . ? Cl2 O8 1.477(6) . ? Cl2 O8A 1.508(12) . ? Cl2 O7B 1.566(8) . ? O5 O7A 0.626(12) . ? O5 O5B 0.734(17) . ? O6 O6B 0.640(17) . ? O6 O8A 1.242(18) . ? O6 O5A 1.311(16) . ? O7 O7B 0.529(13) . ? O7 O5A 1.487(15) . ? O8 O6A 0.644(13) . ? O8 O8B 0.657(14) . ? O5A O6B 1.234(18) . ? O5A O5B 1.78(2) . ? O6A O8B 1.233(18) . ? O6A O7B 1.806(15) . ? O7A O5B 1.28(2) . ? O8A O5B 1.69(2) . ? O8A O8B 1.71(2) . ? O8A O6B 1.77(2) . ? Cl3 O10 1.401(4) . ? Cl3 O9 1.413(3) . ? Cl3 O11 1.419(4) . ? Cl3 O12 1.424(4) . ? O10 O13 1.525(7) ? ? O1S H1S2 0.76(2) . ? O1S H1S1 0.76(2) . ? O2S H2S1 0.75(2) . ? O2S H2S2 0.75(2) . ? 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 O13 Cu1 N2 177.03(13) . . ? O13 Cu1 N1 97.00(12) . . ? N2 Cu1 N1 80.85(11) . . ? O13 Cu1 S1 96.44(9) . . ? N2 Cu1 S1 85.55(8) . . ? N1 Cu1 S1 165.78(8) . . ? O13 Cu1 O11 90.75(14) . 1_455 ? N2 Cu1 O11 91.08(12) . 1_455 ? N1 Cu1 O11 84.71(13) . 1_455 ? S1 Cu1 O11 99.75(10) . 1_455 ? O13 Cu1 O7 107.9(2) . . ? N2 Cu1 O7 70.1(2) . . ? N1 Cu1 O7 86.7(2) . . ? S1 Cu1 O7 84.8(2) . . ? O11 Cu1 O7 160.3(2) 1_455 . ? Cu1 O13 H13A 111(4) . . ? Cu1 O13 H13B 122(4) . . ? H13A O13 H13B 106(4) . . ? N1 C1 C2 122.7(3) . . ? N1 C1 C6 115.4(3) . . ? C2 C1 C6 121.9(3) . . ? C1 C2 C3 117.2(4) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.2(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 121.9(4) . . ? N1 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 N1 C1 118.6(3) . . ? C5 N1 Cu1 129.8(3) . . ? C1 N1 Cu1 111.6(2) . . ? N2 C6 C1 114.5(3) . . ? N2 C6 H6 122.8 . . ? C1 C6 H6 122.8 . . ? C6 N2 N3 122.1(3) . . ? C6 N2 Cu1 117.6(2) . . ? N3 N2 Cu1 120.17(18) . . ? C7 N3 N2 116.0(2) . . ? C7 N3 H3A 122.0 . . ? N2 N3 H3A 122.0 . . ? N4 C7 N3 118.2(3) . . ? N4 C7 S1 118.9(2) . . ? N3 C7 S1 122.9(2) . . ? C7 S1 Cu1 94.94(11) . . ? C7 N4 N5 118.1(2) . . ? C7 N4 H4A 121.0 . . ? N5 N4 H4A 121.0 . . ? C8 N5 N4 116.2(2) . . ? N5 C8 C9 117.9(3) . . ? N5 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? N6 C9 C13 118.3(3) . . ? N6 C9 C8 118.4(3) . . ? C13 C9 C8 123.3(3) . . ? N6 C10 C11 120.3(3) . . ? N6 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 118.5(3) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 120.5(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C9 C13 C12 119.3(3) . . ? C9 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C10 N6 C9 123.2(3) . . ? C10 N6 H6A 118.4 . . ? C9 N6 H6A 118.4 . . ? O3 Cl1 O4 111.3(3) . . ? O3 Cl1 O2 109.2(2) . . ? O4 Cl1 O2 108.3(2) . . ? O3 Cl1 O1 109.72(18) . . ? O4 Cl1 O1 109.55(17) . . ? O2 Cl1 O1 108.75(18) . . ? O6 Cl2 O6A 101.5(7) . . ? O6 Cl2 O5 114.3(6) . . ? O6A Cl2 O5 132.7(7) . . ? O6 Cl2 O5A 55.6(7) . . ? O6A Cl2 O5A 121.5(8) . . ? O5 Cl2 O5A 104.4(7) . . ? O6 Cl2 O8B 107.4(8) . . ? O6A Cl2 O8B 51.5(8) . . ? O5 Cl2 O8B 87.6(7) . . ? O5A Cl2 O8B 162.1(8) . . ? O6 Cl2 O5B 88.4(9) . . ? O6A Cl2 O5B 161.1(10) . . ? O5 Cl2 O5B 29.9(7) . . ? O5A Cl2 O5B 77.4(9) . . ? O8B Cl2 O5B 110.3(10) . . ? O6 Cl2 O7 110.9(6) . . ? O6A Cl2 O7 85.3(7) . . ? O5 Cl2 O7 107.9(5) . . ? O5A Cl2 O7 62.7(7) . . ? O8B Cl2 O7 126.7(7) . . ? O5B Cl2 O7 106.3(8) . . ? O6 Cl2 O6B 25.9(7) . . ? O6A Cl2 O6B 84.5(8) . . ? O5 Cl2 O6B 138.4(7) . . ? O5A Cl2 O6B 51.0(8) . . ? O8B Cl2 O6B 111.3(8) . . ? O5B Cl2 O6B 109.8(10) . . ? O7 Cl2 O6B 90.3(7) . . ? O6 Cl2 O7A 139.5(7) . . ? O6A Cl2 O7A 113.0(8) . . ? O5 Cl2 O7A 25.2(5) . . ? O5A Cl2 O7A 116.2(7) . . ? O8B Cl2 O7A 80.2(7) . . ? O5B Cl2 O7A 52.8(8) . . ? O7 Cl2 O7A 93.0(6) . . ? O6B Cl2 O7A 162.4(8) . . ? O6 Cl2 O8 108.8(5) . . ? O6A Cl2 O8 25.7(5) . . ? O5 Cl2 O8 109.6(5) . . ? O5A Cl2 O8 146.0(7) . . ? O8B Cl2 O8 26.1(6) . . ? O5B Cl2 O8 135.6(8) . . ? O7 Cl2 O8 104.9(5) . . ? O6B Cl2 O8 100.7(7) . . ? O7A Cl2 O8 95.1(6) . . ? O6 Cl2 O8A 50.5(7) . . ? O6A Cl2 O8A 103.9(8) . . ? O5 Cl2 O8A 78.9(7) . . ? O5A Cl2 O8A 97.8(9) . . ? O8B Cl2 O8A 71.1(9) . . ? O5B Cl2 O8A 70.0(9) . . ? O7 Cl2 O8A 160.2(8) . . ? O6B Cl2 O8A 73.5(9) . . ? O7A Cl2 O8A 99.2(8) . . ? O8 Cl2 O8A 89.6(7) . . ? O6 Cl2 O7B 128.6(6) . . ? O6A Cl2 O7B 74.5(6) . . ? O5 Cl2 O7B 102.9(5) . . ? O5A Cl2 O7B 82.4(7) . . ? O8B Cl2 O7B 108.3(7) . . ? O5B Cl2 O7B 111.8(7) . . ? O7 Cl2 O7B 19.7(5) . . ? O6B Cl2 O7B 105.3(7) . . ? O7A Cl2 O7B 82.4(6) . . ? O8 Cl2 O7B 89.3(5) . . ? O8A Cl2 O7B 178.1(7) . . ? O7A O5 O5B 141(2) . . ? O7A O5 Cl2 81.2(12) . . ? O5B O5 Cl2 76.7(11) . . ? O6B O6 O8A 138(2) . . ? O6B O6 O5A 68.9(18) . . ? O8A O6 O5A 119.2(12) . . ? O6B O6 Cl2 81.9(14) . . ? O8A O6 Cl2 69.5(8) . . ? O5A O6 Cl2 62.9(6) . . ? O7B O7 Cl2 93.1(15) . . ? O7B O7 O5A 150.4(17) . . ? Cl2 O7 O5A 57.6(5) . . ? O7B O7 Cu1 86.5(15) . . ? Cl2 O7 Cu1 149.1(5) . . ? O5A O7 Cu1 116.0(7) . . ? O6A O8 O8B 143(2) . . ? O6A O8 Cl2 71.5(11) . . ? O8B O8 Cl2 72.9(11) . . ? O6B O5A O6 28.9(8) . . ? O6B O5A Cl2 66.1(8) . . ? O6 O5A Cl2 61.5(6) . . ? O6B O5A O7 97.6(11) . . ? O6 O5A O7 113.4(10) . . ? Cl2 O5A O7 59.7(6) . . ? O6B O5A O5B 101.5(11) . . ? O6 O5A O5B 77.7(9) . . ? Cl2 O5A O5B 51.8(6) . . ? O7 O5A O5B 89.2(9) . . ? O8 O6A O8B 18.9(11) . . ? O8 O6A Cl2 82.9(12) . . ? O8B O6A Cl2 65.0(7) . . ? O8 O6A O7B 112.7(16) . . ? O8B O6A O7B 104.5(9) . . ? Cl2 O6A O7B 56.7(5) . . ? O5 O7A O5B 21.1(13) . . ? O5 O7A Cl2 73.6(11) . . ? O5B O7A Cl2 62.8(7) . . ? O6 O8A Cl2 60.1(7) . . ? O6 O8A O5B 83.1(11) . . ? Cl2 O8A O5B 52.9(6) . . ? O6 O8A O8B 99.7(11) . . ? Cl2 O8A O8B 52.3(6) . . ? O5B O8A O8B 87.5(10) . . ? O6 O8A O6B 14.0(8) . . ? Cl2 O8A O6B 51.8(6) . . ? O5B O8A O6B 86.0(9) . . ? O8B O8A O6B 86.2(9) . . ? O5 O5B O7A 17.9(11) . . ? O5 O5B Cl2 73.4(11) . . ? O7A O5B Cl2 64.4(7) . . ? O5 O5B O8A 91.3(17) . . ? O7A O5B O8A 97.8(11) . . ? Cl2 O5B O8A 57.1(7) . . ? O5 O5B O5A 119.1(15) . . ? O7A O5B O5A 104.0(10) . . ? Cl2 O5B O5A 50.8(6) . . ? O8A O5B O5A 78.8(9) . . ? O6 O6B O5A 82.2(19) . . ? O6 O6B Cl2 72.2(13) . . ? O5A O6B Cl2 62.9(7) . . ? O6 O6B O8A 28.0(15) . . ? O5A O6B O8A 92.5(11) . . ? Cl2 O6B O8A 54.7(6) . . ? O7 O7B Cl2 67.2(13) . . ? O7 O7B O6A 96.2(16) . . ? Cl2 O7B O6A 48.8(4) . . ? O8 O8B O6A 18.5(10) . . ? O8 O8B Cl2 81.0(12) . . ? O6A O8B Cl2 63.5(7) . . ? O8 O8B O8A 118.4(17) . . ? O6A O8B O8A 101.6(11) . . ? Cl2 O8B O8A 56.6(6) . . ? O10 Cl3 O9 110.8(2) . . ? O10 Cl3 O11 110.9(3) . . ? O9 Cl3 O11 112.2(2) . . ? O10 Cl3 O12 108.3(3) . . ? O9 Cl3 O12 107.2(3) . . ? O11 Cl3 O12 107.1(3) . . ? Cl3 O10 O13 111.6(4) . ? ? H1S2 O1S H1S1 107(4) . . ? H2S1 O2S H2S2 111(4) . . ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.840 _refine_diff_density_max 0.994 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.072 #====END