# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_20110320b _database_code_depnum_ccdc_archive 'CCDC 868488' #TrackingRef '20110320b.cif' _audit_creation_date 2011-03-23 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C2 Cu N2 S2), 2(C10 H15 N)' _chemical_formula_sum 'C24 H30 Cu2 N6 S4' _chemical_formula_weight 657.86 _chemical_melting_point ? _chemical_oxdiff_formula 'Cu C H N S' _chemical_oxdiff_usercomment NYY-2010.12.007 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.7813(17) _cell_length_b 15.715(3) _cell_length_c 10.4219(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.572(13) _cell_angle_gamma 90.00 _cell_volume 1425.7(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1333 _cell_measurement_temperature 291.15 _cell_measurement_theta_max 26.3084 _cell_measurement_theta_min 3.1288 _exptl_absorpt_coefficient_mu 1.810 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 676 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_unetI/netI 0.0450 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6042 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.14 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2542 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 78.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 18.4204 77.0000 90.0000 88 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 40.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 18.4204 -37.0000 -60.0000 94 #__ type_ start__ end____ width___ exp.time_ 3 omega -78.00 -52.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -19.0454 136.0000 179.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega 18.00 47.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -19.0454 77.0000 -180.0000 29 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0437644000 _diffrn_orient_matrix_UB_12 -0.0380951000 _diffrn_orient_matrix_UB_13 0.0055894000 _diffrn_orient_matrix_UB_21 -0.0687389000 _diffrn_orient_matrix_UB_22 -0.0241752000 _diffrn_orient_matrix_UB_23 -0.0089232000 _diffrn_orient_matrix_UB_31 0.0016798000 _diffrn_orient_matrix_UB_32 0.0000762000 _diffrn_orient_matrix_UB_33 -0.0678619000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1838 _reflns_number_total 2894 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)' _refine_diff_density_max 0.730 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.100 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2894 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0631 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1223P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1805 _refine_ls_wR_factor_ref 0.2154 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.81459(9) 0.27719(5) 0.66100(6) 0.0700(4) Uani 1 1 d . . . S1 S 0.6524(2) 0.36815(10) 0.77262(14) 0.0719(5) Uani 1 1 d . . . S2 S 0.97606(17) 0.36615(9) 0.55208(12) 0.0612(4) Uani 1 1 d . . . N1 N 0.6308(6) 0.6507(3) 0.7357(4) 0.0676(12) Uani 1 1 d . . . N2 N 0.7048(7) 0.2938(3) 1.0180(4) 0.0718(14) Uani 1 1 d . . . N3 N 0.9219(6) 0.2909(3) 0.3073(4) 0.0653(12) Uani 1 1 d . . . C1 C 0.4817(9) 0.6377(4) 0.7043(7) 0.093(2) Uani 1 1 d . . . H1 H 0.4123 0.6694 0.7447 0.111 Uiso 1 1 calc R . . C2 C 0.4285(8) 0.5790(5) 0.6144(6) 0.091(2) Uani 1 1 d . . . H2 H 0.3233 0.5698 0.5961 0.110 Uiso 1 1 calc R . . C3 C 0.5273(6) 0.5327(3) 0.5496(5) 0.0579(13) Uani 1 1 d . . . C4 C 0.6812(8) 0.5480(4) 0.5836(6) 0.0773(17) Uani 1 1 d . . . H4 H 0.7532 0.5179 0.5437 0.093 Uiso 1 1 calc R . . C5 C 0.7292(8) 0.6076(4) 0.6763(6) 0.0807(18) Uani 1 1 d . . . H5 H 0.8337 0.6178 0.6977 0.097 Uiso 1 1 calc R . . C6 C 0.6888(9) 0.7144(4) 0.8367(6) 0.085(2) Uani 1 1 d D . . H6A H 0.7876 0.7358 0.8189 0.102 Uiso 1 1 calc R . . H6B H 0.6181 0.7621 0.8324 0.102 Uiso 1 1 calc R . . C7 C 0.7058(12) 0.6780(5) 0.9678(7) 0.122(3) Uani 1 1 d D . . H7A H 0.7476 0.7224 1.0267 0.147 Uiso 1 1 calc R . . H7B H 0.6030 0.6662 0.9878 0.147 Uiso 1 1 calc R . . C8 C 0.7939(15) 0.6044(6) 1.0001(8) 0.143(5) Uani 1 1 d D . . H8A H 0.8971 0.6145 0.9797 0.172 Uiso 1 1 calc R . . H8B H 0.7506 0.5582 0.9451 0.172 Uiso 1 1 calc R . . C9 C 0.8054(16) 0.5755(8) 1.1392(8) 0.167(6) Uani 1 1 d D . . H9A H 0.8462 0.6221 1.1944 0.201 Uiso 1 1 calc R . . H9B H 0.7026 0.5637 1.1589 0.201 Uiso 1 1 calc R . . C10 C 0.897(2) 0.5031(7) 1.1713(10) 0.179(6) Uani 1 1 d D . . H10A H 0.8690 0.4590 1.1089 0.269 Uiso 1 1 calc R . . H10B H 0.8816 0.4833 1.2558 0.269 Uiso 1 1 calc R . . H10C H 1.0033 0.5176 1.1712 0.269 Uiso 1 1 calc R . . C11 C 0.6846(7) 0.3244(3) 0.9186(5) 0.0633(14) Uani 1 1 d . . . C12 C 0.9417(6) 0.3201(3) 0.4080(5) 0.0554(12) 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 0.0787(6) 0.0882(6) 0.0437(4) 0.0036(3) 0.0104(3) -0.0062(4) S1 0.0815(11) 0.0790(10) 0.0578(8) 0.0132(7) 0.0184(7) 0.0160(8) S2 0.0635(9) 0.0733(9) 0.0475(7) -0.0037(6) 0.0102(6) -0.0103(6) N1 0.075(3) 0.064(3) 0.061(3) -0.001(2) 0.001(2) 0.005(2) N2 0.084(4) 0.086(3) 0.048(2) 0.002(2) 0.015(2) 0.018(3) N3 0.069(3) 0.080(3) 0.048(2) -0.003(2) 0.015(2) -0.012(2) C1 0.074(5) 0.106(5) 0.091(5) -0.035(4) -0.011(4) 0.034(4) C2 0.059(4) 0.113(5) 0.097(5) -0.034(4) -0.009(3) 0.029(4) C3 0.060(3) 0.063(3) 0.050(3) 0.007(2) 0.007(2) 0.008(3) C4 0.073(4) 0.086(4) 0.078(4) -0.016(3) 0.032(3) -0.013(3) C5 0.074(4) 0.092(4) 0.079(4) -0.005(4) 0.022(3) -0.023(4) C6 0.101(6) 0.070(4) 0.079(5) -0.009(3) -0.009(4) -0.001(3) C7 0.150(9) 0.124(7) 0.089(5) -0.038(5) 0.004(6) -0.025(6) C8 0.225(13) 0.107(6) 0.082(5) -0.015(5) -0.036(7) 0.035(7) C9 0.260(17) 0.154(9) 0.075(5) -0.008(5) -0.023(8) 0.044(9) C10 0.310(18) 0.112(7) 0.105(7) 0.005(6) -0.012(9) 0.023(9) C11 0.066(4) 0.067(3) 0.059(3) -0.001(3) 0.013(3) 0.008(3) C12 0.052(3) 0.070(3) 0.046(3) 0.005(2) 0.011(2) -0.005(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 S1 2.4213(16) . ? Cu1 S2 2.3829(15) . ? Cu1 N2 2.004(5) 4_565 ? Cu1 N3 1.995(5) 4_566 ? S1 C11 1.659(6) . ? S2 C12 1.658(5) . ? N1 C1 1.323(8) . ? N1 C5 1.314(8) . ? N1 C6 1.494(7) . ? N2 Cu1 2.004(5) 4_566 ? N2 C11 1.135(7) . ? N3 Cu1 1.995(5) 4_565 ? N3 C12 1.137(6) . ? C1 H1 0.9300 . ? C1 C2 1.353(9) . ? C2 H2 0.9300 . ? C2 C3 1.376(8) . ? C3 C3 1.490(11) 3_666 ? C3 C4 1.373(8) . ? C4 H4 0.9300 . ? C4 C5 1.372(8) . ? C5 H5 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.472(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.407(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.510(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.409(12) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 S2 Cu1 S1 107.89(6) . . ? N2 Cu1 S1 115.46(17) 4_565 . ? N2 Cu1 S2 103.33(14) 4_565 . ? N3 Cu1 S1 101.42(13) 4_566 . ? N3 Cu1 S2 115.36(15) 4_566 . ? N3 Cu1 N2 113.7(2) 4_566 4_565 ? C11 S1 Cu1 99.0(2) . . ? C12 S2 Cu1 97.28(18) . . ? C1 N1 C6 120.8(5) . . ? C5 N1 C1 119.7(5) . . ? C5 N1 C6 119.5(6) . . ? C11 N2 Cu1 156.5(5) . 4_566 ? C12 N3 Cu1 157.1(4) . 4_565 ? N1 C1 H1 119.5 . . ? N1 C1 C2 121.0(6) . . ? C2 C1 H1 119.5 . . ? C1 C2 H2 119.4 . . ? C1 C2 C3 121.2(7) . . ? C3 C2 H2 119.4 . . ? C2 C3 C3 122.6(7) . 3_666 ? C4 C3 C2 116.3(5) . . ? C4 C3 C3 121.1(6) . 3_666 ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.1(6) . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 121.6(6) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? N1 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C7 C6 N1 112.1(5) . . ? C7 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C6 C7 H7A 106.9 . . ? C6 C7 H7B 106.9 . . ? H7A C7 H7B 106.7 . . ? C8 C7 C6 121.8(8) . . ? C8 C7 H7A 106.9 . . ? C8 C7 H7B 106.9 . . ? C7 C8 H8A 108.2 . . ? C7 C8 H8B 108.2 . . ? C7 C8 C9 116.2(9) . . ? H8A C8 H8B 107.4 . . ? C9 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? C8 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C10 C9 C8 115.8(10) . . ? C10 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 S1 179.0(6) . . ? N3 C12 S2 177.2(5) . . ? 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 Cu1 S1 C11 N2 -91(34) . . . . ? Cu1 S2 C12 N3 178(100) . . . . ? Cu1 N2 C11 S1 111(34) 4_566 . . . ? Cu1 N3 C12 S2 -159(11) 4_565 . . . ? S1 Cu1 S2 C12 -129.9(2) . . . . ? S2 Cu1 S1 C11 -129.0(2) . . . . ? N1 C1 C2 C3 -2.0(12) . . . . ? N1 C6 C7 C8 54.6(12) . . . . ? N2 Cu1 S1 C11 116.0(3) 4_565 . . . ? N2 Cu1 S2 C12 -7.2(3) 4_565 . . . ? N3 Cu1 S1 C11 -7.4(3) 4_566 . . . ? N3 Cu1 S2 C12 117.6(2) 4_566 . . . ? C1 N1 C5 C4 -1.2(9) . . . . ? C1 N1 C6 C7 86.6(8) . . . . ? C1 C2 C3 C3 179.7(7) . . . 3_666 ? C1 C2 C3 C4 1.5(10) . . . . ? C2 C3 C4 C5 -0.9(8) . . . . ? C3 C3 C4 C5 -179.1(6) 3_666 . . . ? C3 C4 C5 N1 0.8(9) . . . . ? C5 N1 C1 C2 1.8(10) . . . . ? C5 N1 C6 C7 -94.2(8) . . . . ? C6 N1 C1 C2 -178.9(6) . . . . ? C6 N1 C5 C4 179.5(5) . . . . ? C6 C7 C8 C9 178.2(9) . . . . ? C7 C8 C9 C10 -178.4(12) . . . . ? data_20110919a _database_code_depnum_ccdc_archive 'CCDC 868489' #TrackingRef '20110919a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 Cu N3 S2' _chemical_formula_weight 272.83 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' 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 P21/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 9.6447(3) _cell_length_b 10.2793(4) _cell_length_c 10.6510(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.740(3) _cell_angle_gamma 90.00 _cell_volume 1055.46(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.717 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 2.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6054 _exptl_absorpt_correction_T_max 0.7124 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 4256 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1962 _reflns_number_gt 1452 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0528P)^2^+1.4045P] 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 1962 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _refine_ls_shift/su_max 0.157 _refine_ls_shift/su_mean 0.004 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 0.18773(7) 0.14024(7) 0.61855(6) 0.0783(3) Uani 1 1 d . . . N1 N 0.2402(5) 0.3204(4) 0.2908(4) 0.0749(11) Uani 1 1 d . . . N2 N 0.0139(4) 0.1602(4) 0.5264(4) 0.0715(11) Uani 1 1 d . . . N3 N 0.2917(4) 0.5424(4) 0.6975(4) 0.0671(10) Uani 1 1 d . . . S1 S 0.37665(13) 0.24170(15) 0.51264(13) 0.0802(4) Uani 1 1 d . . . S2 S -0.23078(13) 0.10238(14) 0.38950(13) 0.0745(4) Uani 1 1 d . . . C1 C 0.1766(5) 0.4938(5) 0.7435(5) 0.0723(13) Uani 1 1 d . . . H1 H 0.1747 0.4715 0.8280 0.087 Uiso 1 1 calc R . . C2 C 0.0602(5) 0.4759(5) 0.6683(5) 0.0705(13) Uani 1 1 d . . . H2 H -0.0197 0.4413 0.7017 0.085 Uiso 1 1 calc R . . C3 C 0.0621(4) 0.5098(4) 0.5419(4) 0.0583(11) Uani 1 1 d . . . C4 C 0.1839(4) 0.5604(5) 0.4979(4) 0.0629(11) Uani 1 1 d . . . H4 H 0.1891 0.5837 0.4138 0.075 Uiso 1 1 calc R . . C5 C 0.2959(5) 0.5764(5) 0.5759(5) 0.0704(13) Uani 1 1 d . . . H5 H 0.3769 0.6115 0.5450 0.084 Uiso 1 1 calc R . . C6 C 0.4168(6) 0.5601(7) 0.7812(5) 0.103(2) Uani 1 1 d . . . H6A H 0.3890 0.5887 0.8625 0.155 Uiso 1 1 calc R . . H6B H 0.4766 0.6242 0.7457 0.155 Uiso 1 1 calc R . . H6C H 0.4656 0.4790 0.7894 0.155 Uiso 1 1 calc R . . C7 C 0.2963(5) 0.2871(5) 0.3819(4) 0.0653(12) Uani 1 1 d . . . C8 C -0.0857(5) 0.1373(5) 0.4697(5) 0.0640(11) 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 0.0787(5) 0.0918(5) 0.0634(4) -0.0003(3) -0.0115(3) -0.0078(3) N1 0.087(3) 0.080(3) 0.057(2) 0.006(2) -0.004(2) 0.000(2) N2 0.068(2) 0.068(3) 0.078(3) -0.004(2) -0.009(2) -0.001(2) N3 0.062(2) 0.071(3) 0.068(2) -0.005(2) -0.0029(19) -0.005(2) S1 0.0681(7) 0.0957(10) 0.0762(8) 0.0252(7) -0.0097(6) -0.0077(7) S2 0.0648(7) 0.0720(8) 0.0858(9) -0.0065(7) -0.0102(6) 0.0045(6) C1 0.071(3) 0.086(4) 0.060(3) -0.003(2) 0.003(2) -0.003(3) C2 0.060(3) 0.085(4) 0.066(3) 0.002(3) 0.002(2) -0.008(2) C3 0.062(2) 0.056(3) 0.058(2) -0.006(2) 0.0015(19) 0.007(2) C4 0.061(3) 0.063(3) 0.064(3) 0.005(2) 0.004(2) -0.007(2) C5 0.061(3) 0.073(3) 0.076(3) 0.003(3) 0.005(2) -0.011(2) C6 0.081(4) 0.148(6) 0.080(4) 0.002(4) -0.023(3) -0.027(4) C7 0.070(3) 0.062(3) 0.065(3) 0.003(2) 0.010(2) -0.004(2) C8 0.069(3) 0.059(3) 0.064(3) 0.000(2) 0.008(2) 0.011(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 N2 1.928(4) . ? Cu1 N1 1.931(4) 4_566 ? Cu1 S1 2.4093(15) . ? Cu1 S2 2.5302(16) 3_556 ? N1 C7 1.149(6) . ? N1 Cu1 1.931(4) 4_565 ? N2 C8 1.144(6) . ? N3 C1 1.324(6) . ? N3 C5 1.344(6) . ? N3 C6 1.490(6) . ? S1 C7 1.641(5) . ? S2 C8 1.656(5) . ? S2 Cu1 2.5302(16) 3_556 ? C1 C2 1.372(6) . ? C1 H1 0.9300 . ? C2 C3 1.391(6) . ? C2 H2 0.9300 . ? C3 C4 1.380(6) . ? C3 C3 1.485(8) 3_566 ? C4 C5 1.353(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 131.30(19) . 4_566 ? N2 Cu1 S1 111.97(13) . . ? N1 Cu1 S1 100.02(14) 4_566 . ? N2 Cu1 S2 103.22(13) . 3_556 ? N1 Cu1 S2 101.54(14) 4_566 3_556 ? S1 Cu1 S2 106.48(6) . 3_556 ? C7 N1 Cu1 165.5(4) . 4_565 ? C8 N2 Cu1 161.9(4) . . ? C1 N3 C5 120.3(4) . . ? C1 N3 C6 119.9(4) . . ? C5 N3 C6 119.8(4) . . ? C7 S1 Cu1 100.13(17) . . ? C8 S2 Cu1 95.41(17) . 3_556 ? N3 C1 C2 121.0(5) . . ? N3 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 119.8(5) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 117.3(4) . . ? C4 C3 C3 121.8(5) . 3_566 ? C2 C3 C3 120.9(5) . 3_566 ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? N3 C5 C4 120.9(4) . . ? N3 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 S1 179.2(5) . . ? N2 C8 S2 179.0(5) . . ? 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 N1 Cu1 N2 C8 -118.0(13) 4_566 . . . ? S1 Cu1 N2 C8 114.9(14) . . . . ? S2 Cu1 N2 C8 0.7(14) 3_556 . . . ? N2 Cu1 S1 C7 -5.2(2) . . . . ? N1 Cu1 S1 C7 -147.7(2) 4_566 . . . ? S2 Cu1 S1 C7 106.97(19) 3_556 . . . ? C5 N3 C1 C2 0.7(8) . . . . ? C6 N3 C1 C2 -179.7(5) . . . . ? N3 C1 C2 C3 -0.4(8) . . . . ? C1 C2 C3 C4 0.2(7) . . . . ? C1 C2 C3 C3 179.4(5) . . . 3_566 ? C2 C3 C4 C5 -0.3(7) . . . . ? C3 C3 C4 C5 -179.5(5) 3_566 . . . ? C1 N3 C5 C4 -0.9(8) . . . . ? C6 N3 C5 C4 179.5(5) . . . . ? C3 C4 C5 N3 0.7(8) . . . . ? Cu1 N1 C7 S1 110(31) 4_565 . . . ? Cu1 S1 C7 N1 113(31) . . . . ? Cu1 N2 C8 S2 56(29) . . . . ? Cu1 S2 C8 N2 -57(28) 3_556 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.454 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.081 data_20110929a _database_code_depnum_ccdc_archive 'CCDC 868490' #TrackingRef '20110929a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Cu N3 S2' _chemical_formula_weight 300.88 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' 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 P21/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 10.2175(3) _cell_length_b 11.0524(4) _cell_length_c 10.7815(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.854(3) _cell_angle_gamma 90.00 _cell_volume 1213.16(7) _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 block _exptl_crystal_colour black _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 2.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6304 _exptl_absorpt_correction_T_max 0.7280 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 4298 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2251 _reflns_number_gt 1812 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0411P)^2^+0.7530P] 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 2251 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.84281(5) 0.85854(5) 0.11842(4) 0.05794(19) Uani 1 1 d . . . N1 N 0.9948(3) 1.1492(2) -0.0400(3) 0.0478(7) Uani 1 1 d . . . N2 N 0.7941(3) 0.6775(3) -0.2165(2) 0.0473(7) Uani 1 1 d . . . N3 N 0.2583(2) 0.96585(19) 0.3091(2) 0.0306(5) Uani 1 1 d . . . S1 S 0.78679(8) 1.08802(8) 0.10025(8) 0.0458(2) Uani 1 1 d . . . S2 S 0.67057(9) 0.75561(8) -0.00972(8) 0.0481(2) Uani 1 1 d . . . C1 C 0.9098(3) 1.1250(3) 0.0189(3) 0.0373(7) Uani 1 1 d . . . C3 C 0.1524(3) 1.0279(3) 0.2696(3) 0.0397(7) Uani 1 1 d . . . H3 H 0.1471 1.0619 0.1905 0.048 Uiso 1 1 calc R . . C4 C 0.0500(3) 1.0434(3) 0.3424(3) 0.0429(8) Uani 1 1 d . . . H4 H -0.0232 1.0879 0.3125 0.051 Uiso 1 1 calc R . . C5 C 0.0554(3) 0.9929(2) 0.4602(3) 0.0287(6) Uani 1 1 d . . . C6 C 0.1671(3) 0.9289(3) 0.4993(3) 0.0393(7) Uani 1 1 d . . . H6 H 0.1748 0.8940 0.5781 0.047 Uiso 1 1 calc R . . C7 C 0.2666(3) 0.9163(3) 0.4234(3) 0.0400(7) Uani 1 1 d . . . H7 H 0.3412 0.8728 0.4512 0.048 Uiso 1 1 calc R . . C8 C 0.3697(3) 0.9531(3) 0.2280(3) 0.0387(7) Uani 1 1 d . . . H8 H 0.3442 0.9931 0.1485 0.046 Uiso 1 1 calc R . . C9 C 0.3944(4) 0.8215(3) 0.2021(3) 0.0500(9) Uani 1 1 d . . . H9A H 0.4240 0.7814 0.2784 0.075 Uiso 1 1 calc R . . H9B H 0.4605 0.8148 0.1442 0.075 Uiso 1 1 calc R . . H9C H 0.3146 0.7845 0.1673 0.075 Uiso 1 1 calc R . . C10 C 0.4887(4) 1.0169(3) 0.2879(4) 0.0620(11) Uani 1 1 d . . . H10A H 0.4666 1.0992 0.3053 0.093 Uiso 1 1 calc R . . H10B H 0.5575 1.0154 0.2325 0.093 Uiso 1 1 calc R . . H10C H 0.5179 0.9766 0.3642 0.093 Uiso 1 1 calc R . . C2 C 0.7440(3) 0.7094(3) -0.1306(3) 0.0359(7) 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 0.0604(3) 0.0780(4) 0.0388(3) 0.0024(2) 0.0243(2) -0.0058(2) N1 0.0507(17) 0.0459(16) 0.0492(17) 0.0048(13) 0.0182(14) 0.0074(14) N2 0.0593(18) 0.0534(17) 0.0307(14) -0.0009(12) 0.0123(13) 0.0014(14) N3 0.0330(13) 0.0252(12) 0.0344(13) 0.0007(10) 0.0083(10) 0.0016(11) S1 0.0412(5) 0.0547(5) 0.0435(5) 0.0052(4) 0.0152(4) 0.0063(4) S2 0.0513(5) 0.0577(5) 0.0378(4) -0.0096(4) 0.0185(4) -0.0032(4) C1 0.0408(18) 0.0362(16) 0.0353(16) 0.0004(13) 0.0054(14) 0.0088(14) C3 0.0413(18) 0.0484(19) 0.0293(16) 0.0067(14) 0.0034(13) 0.0057(15) C4 0.0336(17) 0.059(2) 0.0360(17) 0.0080(15) 0.0019(13) 0.0115(16) C5 0.0297(15) 0.0258(13) 0.0307(15) -0.0026(11) 0.0021(12) -0.0048(12) C6 0.0413(18) 0.0419(17) 0.0359(17) 0.0120(14) 0.0094(14) 0.0104(15) C7 0.0382(17) 0.0410(17) 0.0419(18) 0.0115(14) 0.0101(14) 0.0131(15) C8 0.0429(18) 0.0360(16) 0.0397(17) 0.0067(13) 0.0188(14) 0.0047(15) C9 0.061(2) 0.0412(18) 0.051(2) -0.0053(15) 0.0220(17) 0.0100(17) C10 0.050(2) 0.054(2) 0.086(3) -0.005(2) 0.028(2) -0.0105(19) C2 0.0424(17) 0.0377(16) 0.0277(15) 0.0025(13) 0.0038(13) -0.0016(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.926(3) 3_775 ? Cu1 N2 1.930(3) 4_576 ? Cu1 S2 2.4266(10) . ? Cu1 S1 2.6037(10) . ? N1 C1 1.150(4) . ? N1 Cu1 1.926(3) 3_775 ? N2 C2 1.151(4) . ? N2 Cu1 1.930(3) 4_575 ? N3 C3 1.321(4) . ? N3 C7 1.344(4) . ? N3 C8 1.500(3) . ? S1 C1 1.644(3) . ? S2 C2 1.639(3) . ? C3 C4 1.369(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 C5 1.486(5) 3_576 ? C6 C7 1.365(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.503(5) . ? C8 C9 1.507(4) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 133.99(13) 3_775 4_576 ? N1 Cu1 S2 109.83(9) 3_775 . ? N2 Cu1 S2 101.36(9) 4_576 . ? N1 Cu1 S1 101.66(8) 3_775 . ? N2 Cu1 S1 101.43(9) 4_576 . ? S2 Cu1 S1 105.64(4) . . ? C1 N1 Cu1 162.0(3) . 3_775 ? C2 N2 Cu1 166.5(3) . 4_575 ? C3 N3 C7 119.5(2) . . ? C3 N3 C8 120.1(2) . . ? C7 N3 C8 120.3(2) . . ? C1 S1 Cu1 96.29(11) . . ? C2 S2 Cu1 103.89(11) . . ? N1 C1 S1 178.5(3) . . ? N3 C3 C4 121.6(3) . . ? N3 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 117.1(3) . . ? C6 C5 C5 121.9(3) . 3_576 ? C4 C5 C5 121.0(3) . 3_576 ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N3 C7 C6 121.1(3) . . ? N3 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? N3 C8 C10 109.4(3) . . ? N3 C8 C9 110.2(2) . . ? C10 C8 C9 112.9(3) . . ? N3 C8 H8 108.1 . . ? C10 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C2 S2 179.1(3) . . ? 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 N1 Cu1 S1 C1 4.28(14) 3_775 . . . ? N2 Cu1 S1 C1 144.21(15) 4_576 . . . ? S2 Cu1 S1 C1 -110.39(12) . . . . ? N1 Cu1 S2 C2 -0.74(15) 3_775 . . . ? N2 Cu1 S2 C2 -146.39(14) 4_576 . . . ? S1 Cu1 S2 C2 108.16(11) . . . . ? Cu1 N1 C1 S1 -75(13) 3_775 . . . ? Cu1 S1 C1 N1 58(12) . . . . ? C7 N3 C3 C4 0.1(5) . . . . ? C8 N3 C3 C4 -178.6(3) . . . . ? N3 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C3 C4 C5 C5 -179.1(3) . . . 3_576 ? C4 C5 C6 C7 -0.4(5) . . . . ? C5 C5 C6 C7 179.3(3) 3_576 . . . ? C3 N3 C7 C6 0.1(5) . . . . ? C8 N3 C7 C6 178.8(3) . . . . ? C5 C6 C7 N3 0.1(5) . . . . ? C3 N3 C8 C10 114.6(3) . . . . ? C7 N3 C8 C10 -64.1(4) . . . . ? C3 N3 C8 C9 -120.7(3) . . . . ? C7 N3 C8 C9 60.7(4) . . . . ? Cu1 N2 C2 S2 4(21) 4_575 . . . ? Cu1 S2 C2 N2 -135(20) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.478 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.064 data_a _database_code_depnum_ccdc_archive 'CCDC 868491' #TrackingRef 'A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cu2 N6 S4' _chemical_formula_weight 601.76 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' 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 8.4491(4) _cell_length_b 14.2366(5) _cell_length_c 10.4911(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.447(4) _cell_angle_gamma 90.00 _cell_volume 1216.35(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3129 _cell_measurement_theta_min 3.1047 _cell_measurement_theta_max 26.3105 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6422 _exptl_absorpt_correction_T_max 0.7423 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7171 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2262 _reflns_number_gt 1819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1321P)^2^+0.0160P] 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 2262 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1902 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.64806(7) 0.23007(4) 0.80108(5) 0.0708(3) Uani 1 1 d . . . S1 S 0.84613(16) 0.14079(9) 0.72502(12) 0.0753(4) Uani 1 1 d . . . S2 S 0.47987(15) 0.12349(9) 0.88442(11) 0.0690(4) Uani 1 1 d . . . N1 N 0.7622(6) 0.1999(3) 0.4619(4) 0.0776(11) Uani 1 1 d . . . N2 N 0.5438(5) 0.1935(3) 1.1438(4) 0.0680(9) Uani 1 1 d . . . N3 N 0.1053(5) 0.3626(3) 0.7862(4) 0.0662(9) Uani 1 1 d . . . C1 C 0.7963(6) 0.1761(3) 0.5697(5) 0.0649(10) Uani 1 1 d . . . C2 C 0.5178(5) 0.1642(3) 1.0372(5) 0.0596(10) Uani 1 1 d . . . C3 C -0.0471(6) 0.3960(3) 0.7423(5) 0.0720(11) Uani 1 1 d . . . H3 H -0.1240 0.3833 0.7890 0.086 Uiso 1 1 calc R . . C4 C -0.0912(6) 0.4481(3) 0.6309(5) 0.0721(12) Uani 1 1 d . . . H4 H -0.1983 0.4703 0.6019 0.087 Uiso 1 1 calc R . . C5 C 0.0201(5) 0.4691(3) 0.5590(4) 0.0602(10) Uani 1 1 d . . . C6 C 0.1764(6) 0.4315(4) 0.6053(5) 0.0779(13) Uani 1 1 d . . . H6 H 0.2545 0.4422 0.5591 0.094 Uiso 1 1 calc R . . C7 C 0.2166(6) 0.3788(4) 0.7184(5) 0.0774(13) Uani 1 1 d . . . H7 H 0.3219 0.3541 0.7485 0.093 Uiso 1 1 calc R . . C8 C 0.1539(7) 0.3112(4) 0.9155(5) 0.0754(12) Uani 1 1 d . . . H8A H 0.2458 0.2700 0.9167 0.090 Uiso 1 1 calc R . . H8B H 0.0629 0.2726 0.9245 0.090 Uiso 1 1 calc R . . C9 C 0.2016(9) 0.3783(6) 1.0306(6) 0.107(2) Uani 1 1 d . . . H9A H 0.1084 0.4189 1.0269 0.128 Uiso 1 1 calc R . . H9B H 0.2200 0.3418 1.1113 0.128 Uiso 1 1 calc R . . C10 C 0.3427(10) 0.4368(6) 1.0413(8) 0.127(3) Uani 1 1 d . . . H10A H 0.4383 0.3981 1.0512 0.191 Uiso 1 1 calc R . . H10B H 0.3574 0.4771 1.1169 0.191 Uiso 1 1 calc R . . H10C H 0.3270 0.4743 0.9629 0.191 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0807(5) 0.0830(5) 0.0501(4) -0.0007(2) 0.0198(3) -0.0030(3) S1 0.0886(9) 0.0826(8) 0.0565(7) 0.0120(5) 0.0224(6) 0.0219(6) S2 0.0733(7) 0.0799(8) 0.0559(7) -0.0087(5) 0.0208(5) -0.0145(5) N1 0.093(3) 0.090(3) 0.055(2) 0.014(2) 0.028(2) 0.029(2) N2 0.073(2) 0.080(2) 0.055(2) -0.0070(18) 0.0236(17) -0.0152(19) N3 0.070(2) 0.066(2) 0.063(2) 0.0014(16) 0.0186(16) 0.0022(17) C1 0.063(2) 0.069(2) 0.066(3) -0.001(2) 0.024(2) 0.011(2) C2 0.054(2) 0.061(2) 0.067(3) 0.006(2) 0.0212(18) -0.0054(17) C3 0.062(2) 0.082(3) 0.073(3) 0.009(2) 0.018(2) -0.009(2) C4 0.054(2) 0.080(3) 0.078(3) 0.012(2) 0.010(2) -0.009(2) C5 0.067(2) 0.056(2) 0.057(2) -0.0103(17) 0.0156(18) -0.0025(18) C6 0.083(3) 0.085(3) 0.077(3) 0.012(2) 0.040(3) 0.024(3) C7 0.078(3) 0.086(3) 0.074(3) 0.011(2) 0.030(2) 0.027(2) C8 0.083(3) 0.074(3) 0.070(3) 0.017(2) 0.023(2) 0.008(2) C9 0.102(4) 0.136(5) 0.074(4) 0.023(4) 0.010(3) -0.012(4) C10 0.136(6) 0.129(6) 0.097(5) 0.037(4) -0.004(4) -0.010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.976(4) 4_566 ? Cu1 N2 1.977(4) 4_565 ? Cu1 S2 2.3975(12) . ? Cu1 S1 2.4009(13) . ? S1 C1 1.649(5) . ? S2 C2 1.654(5) . ? N1 C1 1.142(6) . ? N1 Cu1 1.976(4) 4_565 ? N2 C2 1.158(6) . ? N2 Cu1 1.977(4) 4_566 ? N3 C3 1.335(6) . ? N3 C7 1.341(6) . ? N3 C8 1.500(6) . ? C3 C4 1.349(7) . ? C3 H3 0.9300 . ? C4 C5 1.387(6) . ? C4 H4 0.9300 . ? C5 C6 1.387(7) . ? C5 C5 1.482(9) 3_566 ? C6 C7 1.368(7) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.507(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.435(10) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 116.3(2) 4_566 4_565 ? N1 Cu1 S2 102.12(12) 4_566 . ? N2 Cu1 S2 118.50(13) 4_565 . ? N1 Cu1 S1 109.03(14) 4_566 . ? N2 Cu1 S1 102.07(10) 4_565 . ? S2 Cu1 S1 108.63(5) . . ? C1 S1 Cu1 98.62(15) . . ? C2 S2 Cu1 98.71(14) . . ? C1 N1 Cu1 158.8(3) . 4_565 ? C2 N2 Cu1 158.7(3) . 4_566 ? C3 N3 C7 120.3(4) . . ? C3 N3 C8 119.5(4) . . ? C7 N3 C8 120.1(4) . . ? N1 C1 S1 179.5(4) . . ? N2 C2 S2 179.4(4) . . ? N3 C3 C4 120.9(4) . . ? N3 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 121.3(4) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 116.5(4) . . ? C6 C5 C5 120.5(5) . 3_566 ? C4 C5 C5 123.0(5) . 3_566 ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N3 C7 C6 120.4(4) . . ? N3 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? N3 C8 C9 111.4(4) . . ? N3 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N3 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C8 118.0(6) . . ? C10 C9 H9A 107.8 . . ? C8 C9 H9A 107.8 . . ? C10 C9 H9B 107.8 . . ? C8 C9 H9B 107.8 . . ? H9A C9 H9B 107.1 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 N1 Cu1 S1 C1 -128.3(2) 4_566 . . . ? N2 Cu1 S1 C1 -4.8(2) 4_565 . . . ? S2 Cu1 S1 C1 121.17(18) . . . . ? N1 Cu1 S2 C2 6.2(2) 4_566 . . . ? N2 Cu1 S2 C2 -122.9(2) 4_565 . . . ? S1 Cu1 S2 C2 121.34(16) . . . . ? Cu1 N1 C1 S1 160(100) 4_565 . . . ? Cu1 S1 C1 N1 -156(100) . . . . ? Cu1 N2 C2 S2 -65(35) 4_566 . . . ? Cu1 S2 C2 N2 56(35) . . . . ? C7 N3 C3 C4 -1.3(7) . . . . ? C8 N3 C3 C4 175.4(5) . . . . ? N3 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 1.9(7) . . . . ? C3 C4 C5 C5 -176.1(5) . . . 3_566 ? C4 C5 C6 C7 -1.8(7) . . . . ? C5 C5 C6 C7 176.3(5) 3_566 . . . ? C3 N3 C7 C6 1.5(8) . . . . ? C8 N3 C7 C6 -175.2(5) . . . . ? C5 C6 C7 N3 0.1(8) . . . . ? C3 N3 C8 C9 -82.7(6) . . . . ? C7 N3 C8 C9 94.0(6) . . . . ? N3 C8 C9 C10 -63.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.797 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.158 data_4 _database_code_depnum_ccdc_archive 'CCDC 885944' #TrackingRef 'li-4.cif' _audit_creation_date 2012-05-29 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H17 Cu2 N5 S3' _chemical_formula_sum 'C17 H17 Cu2 N5 S3' _chemical_formula_weight 514.62 _chemical_melting_point ? _chemical_oxdiff_formula C17H17Cu2N5S3 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' Cu Cu 0.3201 1.2651 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 11.6590(4) _cell_length_b 12.0484(3) _cell_length_c 28.1225(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3950.4(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4077 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 26.3126 _cell_measurement_theta_min 3.2550 _exptl_absorpt_coefficient_mu 2.483 _exptl_absorpt_correction_T_max 0.880 _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 2080 _exptl_crystal_size_max 0.2842 _exptl_crystal_size_mid 0.2497 _exptl_crystal_size_min 0.1604 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_unetI/netI 0.0498 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 11431 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.26 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -34.00 13.00 0.5000 18.0000 omega____ theta____ kappa____ phi______ frames - -17.1323 77.0000 -150.0000 94 #__ type_ start__ end____ width___ exp.time_ 2 omega -36.00 21.00 0.5000 18.0000 omega____ theta____ kappa____ phi______ frames - -17.1323 77.0000 60.0000 114 #__ type_ start__ end____ width___ exp.time_ 3 omega -9.00 54.00 0.5000 18.0000 omega____ theta____ kappa____ phi______ frames - 19.8666 77.0000 -30.0000 126 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0381410000 _diffrn_orient_matrix_UB_12 -0.0394796000 _diffrn_orient_matrix_UB_13 0.0100177000 _diffrn_orient_matrix_UB_21 0.0022957000 _diffrn_orient_matrix_UB_22 -0.0317200000 _diffrn_orient_matrix_UB_23 -0.0212152000 _diffrn_orient_matrix_UB_31 0.0473396000 _diffrn_orient_matrix_UB_32 -0.0301326000 _diffrn_orient_matrix_UB_33 0.0092207000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3107 _reflns_number_total 4025 _reflns_odcompleteness_completeness 99.67 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.019 _refine_diff_density_min -1.199 _refine_diff_density_rms 0.110 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment CONSTR _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 4025 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0488 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+3.1718P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1218 _refine_ls_wR_factor_ref 0.1448 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.21461(5) 0.10089(4) 0.41657(2) 0.0485(2) Uani 1 1 d . . . Cu2 Cu -0.03662(7) -0.01700(5) 0.40779(2) 0.0673(2) Uani 1 1 d . . . S1 S 0.16060(9) -0.04317(8) 0.36165(4) 0.0389(3) Uani 1 1 d . . . S2 S 0.01838(10) 0.16487(8) 0.43944(4) 0.0424(3) Uani 1 1 d . . . S3 S -0.27059(12) -0.00109(11) 0.27260(5) 0.0575(3) Uani 1 1 d . . . N1 N 0.2229(3) -0.2578(3) 0.39192(13) 0.0427(8) Uani 1 1 d . . . N2 N 0.0301(4) 0.1113(3) 0.53661(14) 0.0504(9) Uani 1 1 d . . . N3 N -0.1531(4) -0.0136(3) 0.35864(15) 0.0539(10) Uani 1 1 d . . . N4 N 0.2892(3) 0.0375(3) 0.47606(12) 0.0373(8) Uani 1 1 d . . . N5 N 0.5211(3) -0.1809(3) 0.68899(11) 0.0346(7) Uani 1 1 d . . . C1 C 0.1986(3) -0.1689(3) 0.38049(14) 0.0344(8) Uani 1 1 d . . . C2 C 0.0257(4) 0.1339(3) 0.49690(16) 0.0398(9) Uani 1 1 d . . . C3 C -0.2011(4) -0.0079(3) 0.32301(17) 0.0437(10) Uani 1 1 d . . . C4 C 0.2703(4) -0.0670(4) 0.49024(16) 0.0523(12) Uani 1 1 d . . . H4 H 0.2258 -0.1125 0.4710 0.063 Uiso 1 1 calc R . . C5 C 0.3134(4) -0.1109(3) 0.53188(16) 0.0485(11) Uani 1 1 d . . . H5 H 0.2984 -0.1845 0.5397 0.058 Uiso 1 1 calc R . . C6 C 0.3784(3) -0.0463(3) 0.56186(14) 0.0330(8) Uani 1 1 d . . . C7 C 0.3961(4) 0.0618(3) 0.54761(18) 0.0562(13) Uani 1 1 d . . . H7 H 0.4383 0.1096 0.5668 0.067 Uiso 1 1 calc R . . C8 C 0.3521(4) 0.0995(3) 0.50523(17) 0.0534(12) Uani 1 1 d . . . H8 H 0.3671 0.1726 0.4965 0.064 Uiso 1 1 calc R . . C9 C 0.5560(4) -0.0815(3) 0.67326(15) 0.0403(9) Uani 1 1 d . . . H9 H 0.6119 -0.0430 0.6901 0.048 Uiso 1 1 calc R . . C10 C 0.5111(4) -0.0356(3) 0.63284(15) 0.0393(9) Uani 1 1 d . . . H10 H 0.5370 0.0333 0.6225 0.047 Uiso 1 1 calc R . . C11 C 0.4265(3) -0.0918(3) 0.60698(13) 0.0321(8) Uani 1 1 d . . . C12 C 0.3914(4) -0.1938(3) 0.62457(15) 0.0428(10) Uani 1 1 d . . . H12 H 0.3349 -0.2337 0.6086 0.051 Uiso 1 1 calc R . . C13 C 0.4388(4) -0.2363(3) 0.66505(15) 0.0450(10) Uani 1 1 d . . . H13 H 0.4140 -0.3047 0.6763 0.054 Uiso 1 1 calc R . . C14 C 0.5755(4) -0.2317(4) 0.73190(14) 0.0410(9) Uani 1 1 d . . . H14A H 0.6543 -0.2064 0.7340 0.049 Uiso 1 1 calc R . . H14B H 0.5769 -0.3117 0.7280 0.049 Uiso 1 1 calc R . . C15 C 0.5143(4) -0.2040(4) 0.77827(15) 0.0454(10) Uani 1 1 d . . . H15 H 0.5107 -0.1230 0.7810 0.055 Uiso 1 1 calc R . . C16 C 0.5883(5) -0.2475(4) 0.81889(15) 0.0576(13) Uani 1 1 d . . . H16A H 0.5962 -0.3265 0.8161 0.086 Uiso 1 1 calc R . . H16B H 0.5525 -0.2299 0.8487 0.086 Uiso 1 1 calc R . . H16C H 0.6626 -0.2134 0.8175 0.086 Uiso 1 1 calc R . . C17 C 0.3932(4) -0.2481(6) 0.7809(2) 0.0803(18) Uani 1 1 d . . . H17A H 0.3467 -0.2115 0.7574 0.121 Uiso 1 1 calc R . . H17B H 0.3623 -0.2342 0.8120 0.121 Uiso 1 1 calc R . . H17C H 0.3936 -0.3265 0.7749 0.121 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0617(4) 0.0424(3) 0.0414(3) 0.0118(2) -0.0038(3) -0.0032(2) Cu2 0.1065(6) 0.0551(4) 0.0402(4) 0.0052(3) -0.0146(3) 0.0043(3) S1 0.0534(6) 0.0294(5) 0.0340(5) -0.0004(4) -0.0026(5) 0.0014(4) S2 0.0597(7) 0.0320(5) 0.0355(5) 0.0036(4) 0.0046(5) 0.0101(4) S3 0.0610(8) 0.0624(7) 0.0492(7) 0.0022(6) -0.0032(6) -0.0131(6) N1 0.051(2) 0.0332(17) 0.044(2) 0.0013(16) -0.0063(17) 0.0039(15) N2 0.077(3) 0.0342(18) 0.040(2) 0.0004(17) 0.001(2) -0.0040(17) N3 0.067(3) 0.042(2) 0.052(2) -0.0015(19) -0.010(2) 0.0130(18) N4 0.0464(19) 0.0326(16) 0.0329(17) 0.0036(15) -0.0045(15) 0.0013(14) N5 0.0355(17) 0.0390(17) 0.0293(16) -0.0052(15) 0.0002(14) 0.0069(13) C1 0.038(2) 0.036(2) 0.0292(19) -0.0066(17) -0.0011(16) -0.0027(16) C2 0.053(2) 0.0278(18) 0.039(2) -0.0040(18) 0.004(2) 0.0007(16) C3 0.049(2) 0.034(2) 0.048(3) 0.001(2) 0.005(2) 0.0016(18) C4 0.074(3) 0.042(2) 0.041(2) 0.007(2) -0.021(2) -0.022(2) C5 0.069(3) 0.035(2) 0.042(2) 0.0069(19) -0.016(2) -0.016(2) C6 0.034(2) 0.0314(18) 0.034(2) -0.0034(16) 0.0007(17) 0.0016(15) C7 0.083(3) 0.032(2) 0.054(3) 0.003(2) -0.035(3) -0.014(2) C8 0.077(3) 0.029(2) 0.054(3) 0.006(2) -0.020(3) -0.012(2) C9 0.039(2) 0.047(2) 0.035(2) -0.0030(19) -0.0044(18) -0.0068(18) C10 0.044(2) 0.037(2) 0.037(2) -0.0021(18) -0.0001(19) -0.0088(17) C11 0.035(2) 0.0318(19) 0.0294(18) -0.0031(16) -0.0008(17) 0.0029(15) C12 0.055(3) 0.0324(19) 0.041(2) 0.0000(18) -0.016(2) -0.0081(18) C13 0.062(3) 0.033(2) 0.039(2) -0.0007(19) -0.007(2) -0.0055(19) C14 0.042(2) 0.050(2) 0.032(2) 0.0008(19) -0.0015(18) 0.0109(18) C15 0.059(3) 0.040(2) 0.038(2) -0.001(2) 0.007(2) 0.0096(19) C16 0.093(4) 0.047(2) 0.033(2) -0.002(2) -0.004(3) 0.002(2) C17 0.054(3) 0.111(5) 0.076(4) 0.032(4) 0.011(3) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 S1 2.4072(11) . ? Cu1 S2 2.4984(12) . ? Cu1 N1 1.977(3) 7_665 ? Cu1 N4 2.034(3) . ? Cu2 S1 2.6590(14) . ? Cu2 S2 2.4506(13) . ? Cu2 N2 1.934(4) 5_556 ? Cu2 N3 1.938(4) . ? S1 C1 1.665(4) . ? S2 C2 1.661(4) . ? S3 C3 1.635(5) . ? N1 Cu1 1.977(3) 7_655 ? N1 C1 1.153(5) . ? N2 Cu2 1.934(4) 5_556 ? N2 C2 1.151(6) . ? N3 C3 1.150(6) . ? N4 C4 1.340(5) . ? N4 C8 1.330(5) . ? N5 C9 1.340(5) . ? N5 C13 1.348(5) . ? N5 C14 1.494(5) . ? C4 H4 0.9300 . ? C4 C5 1.379(6) . ? C5 H5 0.9300 . ? C5 C6 1.375(6) . ? C6 C7 1.378(6) . ? C6 C11 1.492(5) . ? C7 H7 0.9300 . ? C7 C8 1.375(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C9 C10 1.368(6) . ? C10 H10 0.9300 . ? C10 C11 1.400(5) . ? C11 C12 1.387(5) . ? C12 H12 0.9300 . ? C12 C13 1.365(6) . ? C13 H13 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.524(6) . ? C15 H15 0.9800 . ? C15 C16 1.524(6) . ? C15 C17 1.509(7) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 S1 Cu1 S2 98.52(4) . . ? N1 Cu1 S1 119.49(11) 7_665 . ? N1 Cu1 S2 99.32(11) 7_665 . ? N1 Cu1 N4 116.98(14) 7_665 . ? N4 Cu1 S1 111.66(10) . . ? N4 Cu1 S2 107.20(10) . . ? S2 Cu2 S1 93.27(4) . . ? N2 Cu2 S1 106.90(13) 5_556 . ? N2 Cu2 S2 102.78(11) 5_556 . ? N2 Cu2 N3 128.06(18) 5_556 . ? N3 Cu2 S1 105.09(13) . . ? N3 Cu2 S2 115.07(11) . . ? Cu1 S1 Cu2 80.07(4) . . ? C1 S1 Cu1 112.47(14) . . ? C1 S1 Cu2 100.54(14) . . ? Cu2 S2 Cu1 82.54(4) . . ? C2 S2 Cu1 97.68(15) . . ? C2 S2 Cu2 99.54(14) . . ? C1 N1 Cu1 170.9(3) . 7_655 ? C2 N2 Cu2 157.7(3) . 5_556 ? C3 N3 Cu2 164.6(4) . . ? C4 N4 Cu1 121.8(3) . . ? C8 N4 Cu1 122.2(3) . . ? C8 N4 C4 115.8(3) . . ? C9 N5 C13 119.6(3) . . ? C9 N5 C14 120.2(3) . . ? C13 N5 C14 120.2(3) . . ? N1 C1 S1 177.2(4) . . ? N2 C2 S2 179.2(4) . . ? N3 C3 S3 179.2(5) . . ? N4 C4 H4 118.2 . . ? N4 C4 C5 123.6(4) . . ? C5 C4 H4 118.2 . . ? C4 C5 H5 119.9 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 116.1(4) . . ? C5 C6 C11 121.4(3) . . ? C7 C6 C11 122.5(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 C6 120.6(4) . . ? C8 C7 H7 119.7 . . ? N4 C8 C7 123.7(4) . . ? N4 C8 H8 118.2 . . ? C7 C8 H8 118.2 . . ? N5 C9 H9 119.4 . . ? N5 C9 C10 121.3(4) . . ? C10 C9 H9 119.4 . . ? C9 C10 H10 119.8 . . ? C9 C10 C11 120.4(4) . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 122.0(3) . . ? C12 C11 C6 121.2(3) . . ? C12 C11 C10 116.8(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? N5 C13 C12 121.3(4) . . ? N5 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? N5 C14 H14A 108.8 . . ? N5 C14 H14B 108.8 . . ? N5 C14 C15 113.7(3) . . ? H14A C14 H14B 107.7 . . ? C15 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C14 C15 H15 107.8 . . ? C16 C15 C14 107.5(4) . . ? C16 C15 H15 107.8 . . ? C17 C15 C14 113.7(4) . . ? C17 C15 H15 107.8 . . ? C17 C15 C16 111.9(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 Cu1 S1 C1 N1 177(100) . . . . ? Cu1 S2 C2 N2 -103(35) . . . . ? Cu1 N1 C1 S1 151(7) 7_655 . . . ? Cu1 N4 C4 C5 -175.7(4) . . . . ? Cu1 N4 C8 C7 174.6(4) . . . . ? Cu2 S1 C1 N1 94(8) . . . . ? Cu2 S2 C2 N2 -19(35) . . . . ? Cu2 N2 C2 S2 34(36) 5_556 . . . ? Cu2 N3 C3 S3 138(36) . . . . ? S1 Cu1 S2 Cu2 19.03(4) . . . . ? S1 Cu1 S2 C2 117.72(14) . . . . ? S1 Cu1 N4 C4 -23.4(4) . . . . ? S1 Cu1 N4 C8 162.1(3) . . . . ? S1 Cu2 S2 Cu1 -17.00(4) . . . . ? S1 Cu2 S2 C2 -113.59(16) . . . . ? S1 Cu2 N3 C3 -15.4(14) . . . . ? S2 Cu1 S1 Cu2 -17.61(4) . . . . ? S2 Cu1 S1 C1 -115.00(15) . . . . ? S2 Cu1 N4 C4 83.4(4) . . . . ? S2 Cu1 N4 C8 -91.1(4) . . . . ? S2 Cu2 S1 Cu1 17.79(4) . . . . ? S2 Cu2 S1 C1 129.02(14) . . . . ? S2 Cu2 N3 C3 85.6(14) . . . . ? N1 Cu1 S1 Cu2 -123.44(12) 7_665 . . . ? N1 Cu1 S1 C1 139.17(19) 7_665 . . . ? N1 Cu1 S2 Cu2 140.97(11) 7_665 . . . ? N1 Cu1 S2 C2 -120.35(18) 7_665 . . . ? N1 Cu1 N4 C4 -166.2(3) 7_665 . . . ? N1 Cu1 N4 C8 19.3(4) 7_665 . . . ? N2 Cu2 S1 Cu1 -86.63(12) 5_556 . . . ? N2 Cu2 S1 C1 24.60(18) 5_556 . . . ? N2 Cu2 S2 Cu1 91.15(13) 5_556 . . . ? N2 Cu2 S2 C2 -5.44(19) 5_556 . . . ? N2 Cu2 N3 C3 -141.8(13) 5_556 . . . ? N3 Cu2 S1 Cu1 134.85(12) . . . . ? N3 Cu2 S1 C1 -113.92(18) . . . . ? N3 Cu2 S2 Cu1 -125.33(15) . . . . ? N3 Cu2 S2 C2 138.1(2) . . . . ? N4 Cu1 S1 Cu2 94.80(11) . . . . ? N4 Cu1 S1 C1 -2.59(19) . . . . ? N4 Cu1 S2 Cu2 -96.88(10) . . . . ? N4 Cu1 S2 C2 1.80(17) . . . . ? N4 C4 C5 C6 0.9(8) . . . . ? N5 C9 C10 C11 0.3(6) . . . . ? N5 C14 C15 C16 -172.2(4) . . . . ? N5 C14 C15 C17 63.4(5) . . . . ? C4 N4 C8 C7 -0.2(7) . . . . ? C4 C5 C6 C7 0.2(7) . . . . ? C4 C5 C6 C11 -179.6(4) . . . . ? C5 C6 C7 C8 -1.2(7) . . . . ? C5 C6 C11 C10 166.7(4) . . . . ? C5 C6 C11 C12 -11.6(6) . . . . ? C6 C7 C8 N4 1.2(8) . . . . ? C6 C11 C12 C13 177.8(4) . . . . ? C7 C6 C11 C10 -13.1(6) . . . . ? C7 C6 C11 C12 168.6(4) . . . . ? C8 N4 C4 C5 -0.9(7) . . . . ? C9 N5 C13 C12 1.0(6) . . . . ? C9 N5 C14 C15 91.9(5) . . . . ? C9 C10 C11 C6 -177.9(4) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C10 C11 C12 C13 -0.5(6) . . . . ? C11 C6 C7 C8 178.6(4) . . . . ? C11 C12 C13 N5 -0.2(7) . . . . ? C13 N5 C9 C10 -1.1(6) . . . . ? C13 N5 C14 C15 -90.0(5) . . . . ? C14 N5 C9 C10 177.0(4) . . . . ? C14 N5 C13 C12 -177.1(4) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -8 -6 -32 0.1166 -8.0000 -6.0001 -32.0000 0.2214 0.8508 -0.4930 11 -13 1 0.1137 11.0000 -12.9997 1.0002 0.1037 0.4164 0.9217 -11 12 -3 0.1074 -11.0000 11.9997 -3.0002 -0.0842 -0.3422 -0.9100 6 13 -20 0.1296 6.0000 13.0002 -19.9999 -0.9424 0.0257 -0.2921 -11 -10 16 0.0969 -11.0000 -10.0003 15.9998 0.9746 -0.0475 -0.0719 12 -10 16 0.1037 12.0000 -9.9997 16.0002 0.0974 0.0053 1.0169 -8 12 -20 0.0859 -8.0000 11.9998 -20.0001 -0.3690 0.0253 -0.9247 12 10 -15 0.1210 12.0000 10.0003 -14.9998 -1.0028 0.0286 0.1284 -1 0 -40 0.0917 -1.0000 0.0001 -39.9999 -0.3626 0.8463 -0.4162 10 -8 -24 0.1110 9.9999 -7.9996 -23.9998 -0.3060 0.7859 0.4931 -10 -8 26 0.0901 -10.0000 -8.0003 25.9998 0.9577 -0.3208 0.0074 4 -2 38 0.0551 4.0000 -2.0000 38.0000 0.3071 -0.7336 0.6000 13 9 8 0.1136 13.0000 9.0003 8.0001 -0.7710 -0.4254 0.4180 data_5 _database_code_depnum_ccdc_archive 'CCDC 906300' #TrackingRef 'li-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 B0 Cu N3 O0 S2' _chemical_formula_weight 314.90 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' B B 0.0013 0.0007 '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 P21/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 11.0461(15) _cell_length_b 10.8682(14) _cell_length_c 11.0982(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.472(2) _cell_angle_gamma 90.00 _cell_volume 1323.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2272 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.83 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 1.945 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6742 _exptl_absorpt_correction_T_max 0.6970 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 7292 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2325 _reflns_number_gt 1788 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0348P)^2^+0.7387P] 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 2325 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0742 _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 Cu1 Cu 0.63950(4) 0.83294(5) 0.89851(3) 0.06759(18) Uani 1 1 d . . . N1 N 0.6808(2) 0.8008(3) 0.7382(2) 0.0582(7) Uani 1 1 d . . . N2 N 0.4926(2) 0.8439(2) 0.9740(2) 0.0536(6) Uani 1 1 d . . . N3 N 0.7392(2) 0.4160(2) 0.8346(2) 0.0540(7) Uani 1 1 d . . . S1 S 0.70037(7) 1.08304(8) 0.89951(7) 0.0554(2) Uani 1 1 d . . . S2 S 0.79819(7) 0.74343(8) 1.03229(6) 0.0530(2) Uani 1 1 d . . . C1 C 0.4140(2) 0.8727(3) 1.0282(2) 0.0435(7) Uani 1 1 d . . . C2 C 0.7282(2) 0.7175(3) 1.1529(2) 0.0438(7) Uani 1 1 d . . . C3 C 0.6439(3) 0.4777(4) 0.7803(3) 0.0744(11) Uani 1 1 d . . . H3 H 0.6413 0.4972 0.6985 0.089 Uiso 1 1 calc R . . C4 C 0.5490(3) 0.5128(4) 0.8435(3) 0.0718(11) Uani 1 1 d . . . H4 H 0.4831 0.5557 0.8044 0.086 Uiso 1 1 calc R . . C5 C 0.5520(2) 0.4842(3) 0.9654(3) 0.0451(7) Uani 1 1 d . . . C6 C 0.6553(3) 0.4267(3) 1.0205(3) 0.0530(8) Uani 1 1 d . . . H6 H 0.6628 0.4107 1.1033 0.064 Uiso 1 1 calc R . . C7 C 0.7468(3) 0.3933(3) 0.9534(3) 0.0570(8) Uani 1 1 d . . . H7 H 0.8156 0.3541 0.9915 0.068 Uiso 1 1 calc R . . C8 C 0.8343(3) 0.3689(3) 0.7614(3) 0.0673(10) Uani 1 1 d . . . H8A H 0.8841 0.3095 0.8097 0.081 Uiso 1 1 calc R . . H8B H 0.7943 0.3259 0.6913 0.081 Uiso 1 1 calc R . . C9 C 0.9150(3) 0.4640(3) 0.7188(3) 0.0595(9) Uani 1 1 d . . . H9 H 0.8636 0.5201 0.6662 0.071 Uiso 1 1 calc R . . C10 C 0.9808(3) 0.5391(4) 0.8166(4) 0.0816(12) Uani 1 1 d . . . H10A H 0.9231 0.5813 0.8602 0.122 Uiso 1 1 calc R . . H10B H 1.0314 0.5981 0.7818 0.122 Uiso 1 1 calc R . . H10C H 1.0306 0.4865 0.8712 0.122 Uiso 1 1 calc R . . C11 C 1.0017(3) 0.4014(4) 0.6405(3) 0.0688(10) Uani 1 1 d . . . H11A H 1.0541 0.3461 0.6895 0.103 Uiso 1 1 calc R . . H11B H 1.0502 0.4625 0.6059 0.103 Uiso 1 1 calc R . . H11C H 0.9556 0.3561 0.5767 0.103 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0649(3) 0.1005(4) 0.0415(2) -0.0003(2) 0.02405(19) 0.0109(2) N1 0.0649(16) 0.0744(19) 0.0373(14) -0.0082(13) 0.0140(12) 0.0004(14) N2 0.0540(14) 0.0566(16) 0.0536(15) 0.0007(12) 0.0216(12) -0.0043(12) N3 0.0476(14) 0.0564(16) 0.0613(17) -0.0173(13) 0.0204(13) -0.0120(12) S1 0.0438(4) 0.0630(5) 0.0622(5) -0.0061(4) 0.0183(4) -0.0016(4) S2 0.0586(5) 0.0613(5) 0.0426(4) 0.0082(4) 0.0210(3) 0.0034(4) C1 0.0434(15) 0.0458(17) 0.0415(16) 0.0017(13) 0.0055(13) -0.0079(13) C2 0.0511(16) 0.0458(17) 0.0348(15) 0.0015(13) 0.0061(13) -0.0001(13) C3 0.055(2) 0.127(3) 0.0424(19) -0.017(2) 0.0118(16) -0.011(2) C4 0.0392(16) 0.131(3) 0.0446(19) -0.013(2) 0.0042(14) 0.0003(19) C5 0.0380(14) 0.0527(18) 0.0459(17) -0.0147(14) 0.0103(12) -0.0147(13) C6 0.0573(18) 0.0520(19) 0.0530(18) 0.0043(15) 0.0197(15) 0.0025(15) C7 0.0543(18) 0.053(2) 0.067(2) 0.0026(16) 0.0206(16) 0.0002(15) C8 0.063(2) 0.066(2) 0.080(2) -0.0236(19) 0.0387(18) -0.0087(17) C9 0.0469(17) 0.065(2) 0.070(2) 0.0017(17) 0.0190(16) 0.0045(15) C10 0.073(2) 0.076(3) 0.100(3) -0.020(2) 0.027(2) -0.013(2) C11 0.0512(18) 0.090(3) 0.070(2) -0.001(2) 0.0248(16) 0.0038(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.912(2) . ? Cu1 N1 1.918(2) . ? Cu1 S2 2.3742(9) . ? Cu1 S1 2.7998(11) . ? N1 C2 1.150(3) 4_575 ? N2 C1 1.154(3) . ? N3 C3 1.334(4) . ? N3 C7 1.334(4) . ? N3 C8 1.489(3) . ? S1 C1 1.643(3) 3_677 ? S2 C2 1.644(3) . ? C1 S1 1.643(3) 3_677 ? C2 N1 1.150(3) 4_576 ? C3 C4 1.380(4) . ? C3 H3 0.9300 . ? C4 C5 1.385(4) . ? C4 H4 0.9300 . ? C5 C6 1.381(4) . ? C5 C5 1.492(5) 3_667 ? C6 C7 1.370(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.477(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.481(5) . ? C9 C11 1.525(4) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 136.06(11) . . ? N2 Cu1 S2 110.78(8) . . ? N1 Cu1 S2 105.63(8) . . ? N2 Cu1 S1 98.80(8) . . ? N1 Cu1 S1 95.65(9) . . ? S2 Cu1 S1 103.61(3) . . ? C2 N1 Cu1 166.7(3) 4_575 . ? C1 N2 Cu1 166.2(2) . . ? C3 N3 C7 119.8(3) . . ? C3 N3 C8 119.7(3) . . ? C7 N3 C8 120.4(3) . . ? C1 S1 Cu1 95.10(10) 3_677 . ? C2 S2 Cu1 101.41(10) . . ? N2 C1 S1 177.6(3) . 3_677 ? N1 C2 S2 179.1(3) 4_576 . ? N3 C3 C4 121.0(3) . . ? N3 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 117.5(3) . . ? C6 C5 C5 121.5(3) . 3_667 ? C4 C5 C5 121.0(4) . 3_667 ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N3 C7 C6 121.3(3) . . ? N3 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C9 C8 N3 115.0(3) . . ? C9 C8 H8A 108.5 . . ? N3 C8 H8A 108.5 . . ? C9 C8 H8B 108.5 . . ? N3 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C8 C9 C10 114.5(3) . . ? C8 C9 C11 108.1(3) . . ? C10 C9 C11 112.0(3) . . ? C8 C9 H9 107.3 . . ? C10 C9 H9 107.3 . . ? C11 C9 H9 107.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 N2 Cu1 N1 C2 -175.2(11) . . . 4_575 ? S2 Cu1 N1 C2 -30.0(12) . . . 4_575 ? S1 Cu1 N1 C2 75.9(12) . . . 4_575 ? N1 Cu1 N2 C1 -129.5(10) . . . . ? S2 Cu1 N2 C1 86.5(10) . . . . ? S1 Cu1 N2 C1 -21.7(11) . . . . ? N2 Cu1 S1 C1 2.96(13) . . . 3_677 ? N1 Cu1 S1 C1 141.34(13) . . . 3_677 ? S2 Cu1 S1 C1 -111.05(10) . . . 3_677 ? N2 Cu1 S2 C2 0.20(14) . . . . ? N1 Cu1 S2 C2 -154.76(14) . . . . ? S1 Cu1 S2 C2 105.29(11) . . . . ? Cu1 N2 C1 S1 85(7) . . . 3_677 ? Cu1 S2 C2 N1 -165(18) . . . 4_576 ? C7 N3 C3 C4 -3.6(5) . . . . ? C8 N3 C3 C4 174.1(3) . . . . ? N3 C3 C4 C5 0.1(6) . . . . ? C3 C4 C5 C6 3.6(5) . . . . ? C3 C4 C5 C5 -177.0(3) . . . 3_667 ? C4 C5 C6 C7 -3.9(5) . . . . ? C5 C5 C6 C7 176.7(3) 3_667 . . . ? C3 N3 C7 C6 3.3(5) . . . . ? C8 N3 C7 C6 -174.4(3) . . . . ? C5 C6 C7 N3 0.5(5) . . . . ? C3 N3 C8 C9 73.0(4) . . . . ? C7 N3 C8 C9 -109.3(4) . . . . ? N3 C8 C9 C10 57.2(4) . . . . ? N3 C8 C9 C11 -177.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.322 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.049