# 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_5 #TrackingRef '5.cif' _audit_creation_date 2012-09-05 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 Cu3 N6 S6, C24 H24 N3' _chemical_formula_sum 'C30 H24 Cu3 N9 S6' _chemical_formula_weight 893.56 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula c20h20n4o4cU1S2 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _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' _cell_length_a 7.94506(10) _cell_length_b 9.93697(12) _cell_length_c 45.0334(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3555.38(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4957 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 71.9436 _cell_measurement_theta_min 3.9232 _exptl_absorpt_coefficient_mu 5.681 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour clorless _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatric _exptl_crystal_F_000 1800 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_unetI/netI 0.0448 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_limit_l_min -55 _diffrn_reflns_number 13114 _diffrn_reflns_theta_full 72.09 _diffrn_reflns_theta_max 72.09 _diffrn_reflns_theta_min 3.93 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -56.00 -31.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 133.0000 -140.0000 50 #__ type_ start__ end____ width___ exp.time_ 2 omega -58.00 -33.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 136.0000 -153.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega -113.00 -88.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -136.0000 153.0000 50 #__ type_ start__ end____ width___ exp.time_ 4 omega -62.00 -37.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 136.0000 37.0000 50 #__ type_ start__ end____ width___ exp.time_ 5 omega -91.00 -66.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -136.0000 142.0000 50 #__ type_ start__ end____ width___ exp.time_ 6 omega -75.00 -50.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 133.0000 -140.0000 50 #__ type_ start__ end____ width___ exp.time_ 7 omega 47.00 72.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.7033 -133.0000 -28.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega 32.00 94.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - 55.7033 -136.0000 153.0000 124 #__ type_ start__ end____ width___ exp.time_ 9 omega 109.00 134.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 136.0000 -153.0000 50 #__ type_ start__ end____ width___ exp.time_ 10 omega 59.00 84.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 -133.0000 -28.0000 50 #__ type_ start__ end____ width___ exp.time_ 11 omega 91.00 176.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 133.0000 -140.0000 170 #__ type_ start__ end____ width___ exp.time_ 12 omega 38.00 71.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 19.0000 -180.0000 66 #__ type_ start__ end____ width___ exp.time_ 13 omega -24.00 2.00 0.5000 2.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 19.0000 -180.0000 52 #__ type_ start__ end____ width___ exp.time_ 14 omega -37.00 29.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 37.0000 -150.0000 132 #__ type_ start__ end____ width___ exp.time_ 15 omega -111.00 -22.00 0.5000 5.0000 omega____ theta____ kappa____ phi______ frames - -42.5000 -57.0000 -60.0000 178 #__ type_ start__ end____ width___ exp.time_ 16 omega 45.00 93.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 -25.0000 -180.0000 96 #__ type_ start__ end____ width___ exp.time_ 17 omega 62.00 94.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 -25.0000 -150.0000 64 #__ type_ start__ end____ width___ exp.time_ 18 omega 80.00 107.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 -111.0000 -180.0000 54 #__ type_ start__ end____ width___ exp.time_ 19 omega 101.00 178.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 111.0000 -90.0000 154 #__ type_ start__ end____ width___ exp.time_ 20 omega 100.00 165.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 111.0000 120.0000 130 #__ type_ start__ end____ width___ exp.time_ 21 omega 39.00 65.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 -25.0000 -90.0000 52 #__ type_ start__ end____ width___ exp.time_ 22 omega 63.00 89.00 0.5000 23.0000 omega____ theta____ kappa____ phi______ frames - 111.4066 -25.0000 -120.0000 52 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0003755000 _diffrn_orient_matrix_UB_12 -0.0136907000 _diffrn_orient_matrix_UB_13 -0.0340777000 _diffrn_orient_matrix_UB_21 -0.0056506000 _diffrn_orient_matrix_UB_22 -0.1543773000 _diffrn_orient_matrix_UB_23 0.0030167000 _diffrn_orient_matrix_UB_31 -0.1937894000 _diffrn_orient_matrix_UB_32 0.0044881000 _diffrn_orient_matrix_UB_33 -0.0001565000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance (Cu) 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 5078 _reflns_number_total 5832 _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _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 'J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.425 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.056 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 433 _refine_ls_number_reflns 5832 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0387 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+0.7362P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0857 _refine_ls_wR_factor_ref 0.0904 _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 iterative _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 0.48823(9) 0.74946(7) 0.287246(14) 0.04659(15) Uani 1 1 d . . . Cu2 Cu 0.01892(11) 0.86409(8) 0.385608(15) 0.0586(2) Uani 1 1 d . . . Cu3 Cu -0.06979(9) 0.37930(7) 0.464361(16) 0.05261(18) Uani 1 1 d . . . S1 S 0.66822(18) 0.81302(15) 0.24785(3) 0.0639(4) Uani 1 1 d . . . S2 S 0.70761(17) 0.81688(16) 0.38378(3) 0.0583(3) Uani 1 1 d . . . S3 S 0.23393(15) 0.87221(13) 0.28686(2) 0.0478(2) Uani 1 1 d . . . S4 S 0.12774(17) 0.55440(14) 0.46397(3) 0.0575(3) Uani 1 1 d . . . S5 S -0.32601(19) 0.47565(13) 0.48044(4) 0.0696(4) Uani 1 1 d . . . S6 S -0.12634(17) 0.30610(13) 0.41452(3) 0.0532(3) Uani 1 1 d . . . N1 N 0.5496(5) 1.0559(4) 0.22496(8) 0.0497(9) Uani 1 1 d . . . N2 N 0.5956(5) 0.7676(4) 0.32604(8) 0.0484(9) Uani 1 1 d . . . N3 N 0.1218(5) 0.8612(4) 0.34613(9) 0.0533(10) Uani 1 1 d . . . N4 N 0.0736(6) 0.7288(5) 0.41651(9) 0.0575(11) Uani 1 1 d . . . N5 N -0.4833(6) 0.2729(4) 0.51280(9) 0.0538(10) Uani 1 1 d . . . N6 N 0.0069(6) 0.0501(4) 0.40365(9) 0.0543(10) Uani 1 1 d . . . N7 N 0.1061(5) 0.5404(4) 0.34341(10) 0.0460(9) Uani 1 1 d . . . N8 N 0.4569(5) 0.0804(5) 0.44545(8) 0.0498(10) Uani 1 1 d . . . N9 N 0.6751(4) 0.1286(4) 0.32014(7) 0.0385(7) Uani 1 1 d . . . C1 C 0.5952(6) 0.9558(5) 0.23491(9) 0.0419(10) Uani 1 1 d . . . C2 C 0.6444(6) 0.7879(5) 0.34945(10) 0.0445(10) Uani 1 1 d . . . C3 C 0.1679(5) 0.8639(4) 0.32181(10) 0.0417(9) Uani 1 1 d . . . C4 C 0.0900(6) 0.6564(5) 0.43582(10) 0.0441(10) Uani 1 1 d . . . C5 C -0.4180(6) 0.3564(5) 0.49960(10) 0.0457(10) Uani 1 1 d . . . C6 C -0.0454(5) 0.1550(5) 0.40874(9) 0.0423(10) Uani 1 1 d . . . C7 C 0.3358(5) 0.4145(4) 0.36741(11) 0.0424(10) Uani 1 1 d . . . C8 C 0.3347(5) 0.3734(5) 0.39646(11) 0.0493(11) Uani 1 1 d . . . H8 H 0.2994 0.4334 0.4110 0.059 Uiso 1 1 calc R . . C9 C 0.3851(5) 0.2443(5) 0.40485(10) 0.0446(10) Uani 1 1 d . . . C10 C 0.4371(5) 0.1552(4) 0.38330(10) 0.0414(9) Uani 1 1 d . . . H10 H 0.4689 0.0683 0.3885 0.050 Uiso 1 1 calc R . . C11 C 0.4419(5) 0.1958(4) 0.35354(10) 0.0363(8) Uani 1 1 d . . . C12 C 0.3912(5) 0.3248(4) 0.34574(9) 0.0381(9) Uani 1 1 d . . . H12 H 0.3944 0.3514 0.3260 0.046 Uiso 1 1 calc R . . C13 C 0.2730(6) 0.5523(5) 0.35832(13) 0.0553(13) Uani 1 1 d . . . H13A H 0.2629 0.6092 0.3757 0.066 Uiso 1 1 calc R . . H13B H 0.3531 0.5938 0.3449 0.066 Uiso 1 1 calc R . . C14 C 0.3707(8) 0.2070(7) 0.43721(11) 0.0666(16) Uani 1 1 d . . . H14A H 0.4170 0.2796 0.4491 0.080 Uiso 1 1 calc R . . H14B H 0.2524 0.1988 0.4422 0.080 Uiso 1 1 calc R . . C15 C 0.5006(6) 0.0991(4) 0.32985(10) 0.0452(10) Uani 1 1 d . . . H15A H 0.4953 0.0080 0.3375 0.054 Uiso 1 1 calc R . . H15B H 0.4257 0.1049 0.3129 0.054 Uiso 1 1 calc R . . C16 C 0.0914(8) 0.5474(5) 0.31330(13) 0.0621(14) Uani 1 1 d . . . H16 H 0.1862 0.5640 0.3017 0.075 Uiso 1 1 calc R . . C17 C -0.0608(9) 0.5303(6) 0.30004(15) 0.0748(17) Uani 1 1 d . . . H17 H -0.0707 0.5353 0.2795 0.090 Uiso 1 1 calc R . . C18 C -0.1999(8) 0.5055(6) 0.31734(15) 0.0705(17) Uani 1 1 d . . . H18 H -0.3046 0.4936 0.3085 0.085 Uiso 1 1 calc R . . C19 C -0.1845(7) 0.4984(5) 0.34737(14) 0.0624(14) Uani 1 1 d . . . H19 H -0.2779 0.4803 0.3592 0.075 Uiso 1 1 calc R . . C20 C -0.0299(6) 0.5181(5) 0.36005(12) 0.0517(11) Uani 1 1 d . . . H20 H -0.0196 0.5160 0.3806 0.062 Uiso 1 1 calc R . . C21 C 0.3742(8) -0.0361(8) 0.44554(13) 0.0748(19) Uani 1 1 d . . . H21 H 0.2608 -0.0375 0.4404 0.090 Uiso 1 1 calc R . . C22 C 0.4529(9) -0.1537(7) 0.45302(14) 0.083(2) Uani 1 1 d . . . H22 H 0.3942 -0.2347 0.4528 0.099 Uiso 1 1 calc R . . C23 C 0.6176(9) -0.1506(6) 0.46075(12) 0.0733(17) Uani 1 1 d . . . H23 H 0.6723 -0.2297 0.4661 0.088 Uiso 1 1 calc R . . C24 C 0.7029(7) -0.0323(6) 0.46067(12) 0.0615(13) Uani 1 1 d . . . H24 H 0.8164 -0.0294 0.4657 0.074 Uiso 1 1 calc R . . C25 C 0.6181(6) 0.0831(5) 0.45308(10) 0.0512(11) Uani 1 1 d . . . H25 H 0.6750 0.1649 0.4533 0.061 Uiso 1 1 calc R . . C26 C 0.8011(5) 0.1277(5) 0.33996(9) 0.0421(9) Uani 1 1 d . . . H26 H 0.7773 0.1100 0.3598 0.051 Uiso 1 1 calc R . . C27 C 0.9635(6) 0.1522(5) 0.33171(10) 0.0478(11) Uani 1 1 d . . . H27 H 1.0494 0.1507 0.3457 0.057 Uiso 1 1 calc R . . C28 C 0.9982(7) 0.1788(5) 0.30266(11) 0.0565(12) Uani 1 1 d . . . H28 H 1.1082 0.1954 0.2967 0.068 Uiso 1 1 calc R . . C29 C 0.8693(8) 0.1808(7) 0.28231(11) 0.0724(18) Uani 1 1 d . . . H29 H 0.8914 0.1989 0.2624 0.087 Uiso 1 1 calc R . . C30 C 0.7085(7) 0.1561(6) 0.29154(10) 0.0588(14) Uani 1 1 d . . . H30 H 0.6209 0.1583 0.2778 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0595(4) 0.0438(3) 0.0365(3) -0.0018(3) -0.0035(3) 0.0020(3) Cu2 0.0810(5) 0.0528(4) 0.0421(3) 0.0031(3) 0.0008(4) 0.0117(4) Cu3 0.0572(4) 0.0466(4) 0.0540(4) 0.0109(4) 0.0009(3) -0.0032(3) S1 0.0670(8) 0.0580(7) 0.0668(8) 0.0233(7) 0.0245(7) 0.0198(6) S2 0.0579(7) 0.0791(9) 0.0378(5) -0.0061(6) -0.0063(5) 0.0024(6) S3 0.0533(6) 0.0519(6) 0.0383(5) -0.0030(5) -0.0039(5) 0.0112(5) S4 0.0697(8) 0.0617(7) 0.0411(5) 0.0138(6) -0.0113(6) -0.0259(6) S5 0.0673(8) 0.0424(6) 0.0992(11) 0.0152(7) 0.0293(8) 0.0056(6) S6 0.0695(8) 0.0496(6) 0.0406(5) 0.0041(5) -0.0023(5) -0.0013(6) N1 0.069(3) 0.0373(19) 0.0422(18) 0.0085(16) -0.0009(18) -0.0012(18) N2 0.057(2) 0.047(2) 0.0415(19) -0.0060(18) -0.0158(18) 0.0102(18) N3 0.070(3) 0.045(2) 0.045(2) -0.0007(19) 0.008(2) 0.008(2) N4 0.069(3) 0.058(3) 0.045(2) 0.018(2) -0.012(2) -0.002(2) N5 0.064(3) 0.049(2) 0.0487(19) 0.0117(19) 0.003(2) -0.001(2) N6 0.066(3) 0.052(2) 0.0453(19) -0.0092(18) 0.001(2) -0.004(2) N7 0.044(2) 0.0297(17) 0.065(2) 0.0073(17) 0.0083(19) 0.0050(15) N8 0.047(2) 0.073(3) 0.0290(16) 0.0035(18) 0.0020(15) -0.0057(19) N9 0.0448(19) 0.0372(17) 0.0336(16) -0.0064(15) -0.0023(14) 0.0104(16) C1 0.044(2) 0.049(3) 0.0321(18) -0.0040(19) 0.0068(17) -0.012(2) C2 0.044(2) 0.042(2) 0.048(2) -0.005(2) -0.002(2) 0.0063(18) C3 0.043(2) 0.0322(19) 0.050(2) -0.006(2) -0.0024(19) 0.0104(18) C4 0.038(2) 0.051(2) 0.044(2) -0.006(2) -0.0020(18) -0.0096(19) C5 0.050(3) 0.045(2) 0.043(2) -0.005(2) -0.0029(19) 0.010(2) C6 0.044(2) 0.054(3) 0.0284(17) 0.0011(18) -0.0020(16) -0.0132(19) C7 0.029(2) 0.039(2) 0.059(3) -0.005(2) 0.0058(19) -0.0017(17) C8 0.034(2) 0.053(3) 0.061(3) -0.020(2) 0.0062(19) 0.000(2) C9 0.034(2) 0.059(3) 0.041(2) -0.002(2) -0.0012(17) 0.002(2) C10 0.0320(19) 0.041(2) 0.052(2) 0.0029(19) -0.0044(18) 0.0024(16) C11 0.0238(18) 0.0378(19) 0.047(2) -0.0023(18) -0.0056(16) -0.0023(16) C12 0.0294(19) 0.040(2) 0.045(2) -0.0011(19) 0.0005(17) -0.0014(16) C13 0.042(3) 0.035(2) 0.089(4) -0.006(3) 0.014(3) -0.0029(19) C14 0.070(4) 0.085(4) 0.045(3) -0.001(3) 0.004(2) 0.017(3) C15 0.045(2) 0.039(2) 0.052(2) -0.0062(19) -0.015(2) 0.0018(19) C16 0.073(4) 0.051(3) 0.063(3) 0.006(3) 0.019(3) 0.008(3) C17 0.094(5) 0.064(3) 0.067(3) 0.006(3) -0.016(3) 0.016(3) C18 0.061(4) 0.050(3) 0.100(5) 0.006(3) -0.019(3) 0.016(2) C19 0.046(3) 0.052(3) 0.089(4) 0.011(3) 0.001(3) 0.005(2) C20 0.046(3) 0.045(2) 0.064(3) 0.006(2) 0.010(2) 0.003(2) C21 0.058(3) 0.105(5) 0.062(3) 0.003(4) -0.007(3) -0.038(4) C22 0.106(5) 0.077(4) 0.066(3) 0.008(3) -0.011(4) -0.046(4) C23 0.113(5) 0.061(3) 0.046(3) 0.010(3) -0.008(3) -0.005(3) C24 0.061(3) 0.070(3) 0.053(3) 0.005(3) -0.005(3) -0.001(3) C25 0.054(3) 0.056(3) 0.043(2) 0.004(2) 0.007(2) -0.015(2) C26 0.045(2) 0.049(2) 0.0320(19) 0.0100(19) -0.0004(17) 0.004(2) C27 0.047(3) 0.048(2) 0.048(2) 0.008(2) 0.001(2) 0.0072(19) C28 0.053(3) 0.059(3) 0.058(3) 0.006(2) 0.017(2) 0.014(3) C29 0.089(4) 0.092(4) 0.036(2) 0.007(3) 0.024(3) 0.030(4) C30 0.071(3) 0.075(4) 0.031(2) -0.008(2) -0.006(2) 0.020(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 2.3648(14) . ? Cu1 S3 2.3602(13) . ? Cu1 N1 2.023(4) 4_645 ? Cu1 N2 1.953(4) . ? Cu2 S2 2.5188(16) 1_455 ? Cu2 N3 1.957(4) . ? Cu2 N4 1.983(4) . ? Cu2 N6 2.021(4) 1_565 ? Cu3 S4 2.3432(14) . ? Cu3 S5 2.3633(16) . ? Cu3 S6 2.4018(14) . ? Cu3 N5 1.954(4) 3_556 ? S1 C1 1.639(5) . ? S2 Cu2 2.5188(16) 1_655 ? S2 C2 1.651(5) . ? S3 C3 1.661(4) . ? S4 C4 1.650(5) . ? S5 C5 1.638(5) . ? S6 C6 1.654(5) . ? N1 Cu1 2.022(4) 4_655 ? N1 C1 1.150(6) . ? N2 C2 1.141(6) . ? N3 C3 1.155(6) . ? N4 C4 1.136(6) . ? N5 Cu3 1.954(4) 3_456 ? N5 C5 1.145(6) . ? N6 Cu2 2.021(4) 1_545 ? N6 C6 1.145(6) . ? N7 C13 1.491(6) . ? N7 C16 1.363(7) . ? N7 C20 1.334(6) . ? N8 C14 1.479(7) . ? N8 C21 1.331(8) . ? N8 C25 1.327(6) . ? N9 C15 1.483(6) . ? N9 C26 1.341(5) . ? N9 C30 1.343(6) . ? C7 C8 1.370(7) . ? C7 C12 1.393(6) . ? C7 C13 1.514(6) . ? C8 H8 0.9300 . ? C8 C9 1.396(7) . ? C9 C10 1.377(6) . ? C9 C14 1.509(6) . ? C10 H10 0.9300 . ? C10 C11 1.400(6) . ? C11 C12 1.389(6) . ? C11 C15 1.509(6) . ? C12 H12 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16 0.9300 . ? C16 C17 1.359(9) . ? C17 H17 0.9300 . ? C17 C18 1.374(9) . ? C18 H18 0.9300 . ? C18 C19 1.360(8) . ? C19 H19 0.9300 . ? C19 C20 1.369(7) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C21 C22 1.368(10) . ? C22 H22 0.9300 . ? C22 C23 1.354(9) . ? C23 H23 0.9300 . ? C23 C24 1.357(8) . ? C24 H24 0.9300 . ? C24 C25 1.373(8) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C26 C27 1.364(6) . ? C27 H27 0.9300 . ? C27 C28 1.363(6) . ? C28 H28 0.9300 . ? C28 C29 1.374(8) . ? C29 H29 0.9300 . ? C29 C30 1.367(8) . ? C30 H30 0.9300 . ? 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 S3 Cu1 S1 111.97(5) . . ? N1 Cu1 S1 98.04(12) 4_645 . ? N1 Cu1 S3 111.23(13) 4_645 . ? N2 Cu1 S1 112.48(14) . . ? N2 Cu1 S3 109.45(12) . . ? N2 Cu1 N1 113.34(17) . 4_645 ? N3 Cu2 S2 112.18(14) . 1_455 ? N3 Cu2 N4 122.41(19) . . ? N3 Cu2 N6 113.48(18) . 1_565 ? N4 Cu2 S2 96.41(14) . 1_455 ? N4 Cu2 N6 110.39(18) . 1_565 ? N6 Cu2 S2 97.87(14) 1_565 1_455 ? S4 Cu3 S5 106.16(6) . . ? S4 Cu3 S6 110.07(5) . . ? S5 Cu3 S6 104.35(6) . . ? N5 Cu3 S4 110.07(14) 3_556 . ? N5 Cu3 S5 117.08(14) 3_556 . ? N5 Cu3 S6 108.87(13) 3_556 . ? C1 S1 Cu1 106.47(16) . . ? C2 S2 Cu2 111.22(17) . 1_655 ? C3 S3 Cu1 103.75(15) . . ? C4 S4 Cu3 109.88(16) . . ? C5 S5 Cu3 104.63(17) . . ? C6 S6 Cu3 110.44(15) . . ? C1 N1 Cu1 167.3(4) . 4_655 ? C2 N2 Cu1 172.4(4) . . ? C3 N3 Cu2 173.4(4) . . ? C4 N4 Cu2 172.5(4) . . ? C5 N5 Cu3 173.5(4) . 3_456 ? C6 N6 Cu2 158.4(4) . 1_545 ? C16 N7 C13 121.3(4) . . ? C20 N7 C13 118.7(4) . . ? C20 N7 C16 119.9(5) . . ? C21 N8 C14 120.8(5) . . ? C25 N8 C14 119.7(5) . . ? C25 N8 C21 119.6(5) . . ? C26 N9 C15 120.0(3) . . ? C26 N9 C30 119.5(4) . . ? C30 N9 C15 120.5(4) . . ? N1 C1 S1 177.0(4) . . ? N2 C2 S2 177.9(5) . . ? N3 C3 S3 178.5(4) . . ? N4 C4 S4 176.0(4) . . ? N5 C5 S5 179.4(5) . . ? N6 C6 S6 177.1(4) . . ? C8 C7 C12 118.7(4) . . ? C8 C7 C13 121.7(5) . . ? C12 C7 C13 119.6(4) . . ? C7 C8 H8 119.0 . . ? C7 C8 C9 122.0(4) . . ? C9 C8 H8 119.0 . . ? C8 C9 C14 117.8(5) . . ? C10 C9 C8 119.1(4) . . ? C10 C9 C14 123.1(5) . . ? C9 C10 H10 120.1 . . ? C9 C10 C11 119.8(4) . . ? C11 C10 H10 120.1 . . ? C10 C11 C15 120.2(4) . . ? C12 C11 C10 120.0(4) . . ? C12 C11 C15 119.9(4) . . ? C7 C12 H12 119.8 . . ? C11 C12 C7 120.3(4) . . ? C11 C12 H12 119.8 . . ? N7 C13 C7 110.0(4) . . ? N7 C13 H13A 109.7 . . ? N7 C13 H13B 109.7 . . ? C7 C13 H13A 109.7 . . ? C7 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N8 C14 C9 114.6(4) . . ? N8 C14 H14A 108.6 . . ? N8 C14 H14B 108.6 . . ? C9 C14 H14A 108.6 . . ? C9 C14 H14B 108.6 . . ? H14A C14 H14B 107.6 . . ? N9 C15 C11 111.8(3) . . ? N9 C15 H15A 109.3 . . ? N9 C15 H15B 109.3 . . ? C11 C15 H15A 109.3 . . ? C11 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? N7 C16 H16 119.8 . . ? C17 C16 N7 120.4(5) . . ? C17 C16 H16 119.8 . . ? C16 C17 H17 120.4 . . ? C16 C17 C18 119.3(6) . . ? C18 C17 H17 120.4 . . ? C17 C18 H18 120.0 . . ? C19 C18 C17 120.0(6) . . ? C19 C18 H18 120.0 . . ? C18 C19 H19 120.4 . . ? C18 C19 C20 119.2(6) . . ? C20 C19 H19 120.4 . . ? N7 C20 C19 121.1(5) . . ? N7 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? N8 C21 H21 119.4 . . ? N8 C21 C22 121.2(6) . . ? C22 C21 H21 119.4 . . ? C21 C22 H22 120.5 . . ? C23 C22 C21 119.1(6) . . ? C23 C22 H22 120.5 . . ? C22 C23 H23 119.9 . . ? C22 C23 C24 120.1(6) . . ? C24 C23 H23 119.9 . . ? C23 C24 H24 120.7 . . ? C23 C24 C25 118.6(5) . . ? C25 C24 H24 120.7 . . ? N8 C25 C24 121.4(5) . . ? N8 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? N9 C26 H26 119.2 . . ? N9 C26 C27 121.6(4) . . ? C27 C26 H26 119.2 . . ? C26 C27 H27 120.4 . . ? C28 C27 C26 119.2(5) . . ? C28 C27 H27 120.4 . . ? C27 C28 H28 120.3 . . ? C27 C28 C29 119.5(5) . . ? C29 C28 H28 120.3 . . ? C28 C29 H29 120.3 . . ? C30 C29 C28 119.4(5) . . ? C30 C29 H29 120.3 . . ? N9 C30 C29 120.9(5) . . ? N9 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? 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 179(100) . . . . ? Cu1 S3 C3 N3 126(17) . . . . ? Cu1 N1 C1 S1 -77(9) 4_655 . . . ? Cu1 N2 C2 S2 43(14) . . . . ? Cu2 S2 C2 N2 -176(100) 1_655 . . . ? Cu2 N3 C3 S3 68(19) . . . . ? Cu2 N4 C4 S4 -131(6) . . . . ? Cu2 N6 C6 S6 -23(10) 1_545 . . . ? Cu3 S4 C4 N4 -156(7) . . . . ? Cu3 S5 C5 N5 -109(100) . . . . ? Cu3 S6 C6 N6 168(9) . . . . ? Cu3 N5 C5 S5 128(100) 3_456 . . . ? S1 Cu1 S3 C3 -156.52(17) . . . . ? S1 Cu1 N2 C2 121(3) . . . . ? S2 Cu2 N3 C3 32(4) 1_455 . . . ? S2 Cu2 N4 C4 -45(3) 1_455 . . . ? S3 Cu1 S1 C1 15.03(18) . . . . ? S3 Cu1 N2 C2 -5(3) . . . . ? S4 Cu3 S5 C5 -145.93(18) . . . . ? S4 Cu3 S6 C6 109.42(17) . . . . ? S5 Cu3 S4 C4 -72.97(19) . . . . ? S5 Cu3 S6 C6 -137.04(17) . . . . ? S6 Cu3 S4 C4 39.4(2) . . . . ? S6 Cu3 S5 C5 97.78(18) . . . . ? N1 Cu1 S1 C1 131.9(2) 4_645 . . . ? N1 Cu1 S3 C3 94.9(2) 4_645 . . . ? N1 Cu1 N2 C2 -129(3) 4_645 . . . ? N2 Cu1 S1 C1 -108.7(2) . . . . ? N2 Cu1 S3 C3 -31.1(2) . . . . ? N3 Cu2 N4 C4 -167(3) . . . . ? N4 Cu2 N3 C3 145(4) . . . . ? N5 Cu3 S4 C4 159.4(2) 3_556 . . . ? N5 Cu3 S5 C5 -22.6(2) 3_556 . . . ? N5 Cu3 S6 C6 -11.3(2) 3_556 . . . ? N6 Cu2 N3 C3 -78(4) 1_565 . . . ? N6 Cu2 N4 C4 56(3) 1_565 . . . ? N7 C16 C17 C18 -0.1(9) . . . . ? N8 C21 C22 C23 0.7(10) . . . . ? N9 C26 C27 C28 0.3(7) . . . . ? C7 C8 C9 C10 -0.2(7) . . . . ? C7 C8 C9 C14 -176.9(5) . . . . ? C8 C7 C12 C11 1.0(6) . . . . ? C8 C7 C13 N7 -106.1(5) . . . . ? C8 C9 C10 C11 1.3(6) . . . . ? C8 C9 C14 N8 -168.4(4) . . . . ? C9 C10 C11 C12 -1.3(6) . . . . ? C9 C10 C11 C15 179.3(4) . . . . ? C10 C9 C14 N8 15.0(7) . . . . ? C10 C11 C12 C7 0.1(6) . . . . ? C10 C11 C15 N9 -102.8(4) . . . . ? C12 C7 C8 C9 -0.9(7) . . . . ? C12 C7 C13 N7 71.9(5) . . . . ? C12 C11 C15 N9 77.8(4) . . . . ? C13 N7 C16 C17 177.1(5) . . . . ? C13 N7 C20 C19 -176.1(4) . . . . ? C13 C7 C8 C9 177.0(4) . . . . ? C13 C7 C12 C11 -177.0(4) . . . . ? C14 N8 C21 C22 179.8(5) . . . . ? C14 N8 C25 C24 -179.5(5) . . . . ? C14 C9 C10 C11 177.8(4) . . . . ? C15 N9 C26 C27 178.9(4) . . . . ? C15 N9 C30 C29 -178.8(5) . . . . ? C15 C11 C12 C7 179.6(4) . . . . ? C16 N7 C13 C7 -101.9(5) . . . . ? C16 N7 C20 C19 1.8(7) . . . . ? C16 C17 C18 C19 0.0(9) . . . . ? C17 C18 C19 C20 1.0(9) . . . . ? C18 C19 C20 N7 -1.9(8) . . . . ? C20 N7 C13 C7 76.0(5) . . . . ? C20 N7 C16 C17 -0.8(8) . . . . ? C21 N8 C14 C9 -93.0(6) . . . . ? C21 N8 C25 C24 1.0(7) . . . . ? C21 C22 C23 C24 -0.8(10) . . . . ? C22 C23 C24 C25 1.0(9) . . . . ? C23 C24 C25 N8 -1.1(8) . . . . ? C25 N8 C14 C9 87.5(6) . . . . ? C25 N8 C21 C22 -0.8(8) . . . . ? C26 N9 C15 C11 58.3(5) . . . . ? C26 N9 C30 C29 1.1(8) . . . . ? C26 C27 C28 C29 0.2(8) . . . . ? C27 C28 C29 C30 0.0(9) . . . . ? C28 C29 C30 N9 -0.6(9) . . . . ? C30 N9 C15 C11 -121.8(5) . . . . ? C30 N9 C26 C27 -1.0(7) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 900604' ####################################################################### # # 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_nyy2012121803 #TrackingRef '2.cif' _audit_creation_date 2012-12-26 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C5 Cu2 N5 S5, C27 H30 N3' _chemical_formula_sum 'C32 H30 Cu2 N8 S5' _chemical_formula_weight 814.02 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C20H20N4O4Cu1S1 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 monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z' _cell_length_a 9.6275(2) _cell_length_b 9.2206(2) _cell_length_c 19.3389(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.532(2) _cell_angle_gamma 90.00 _cell_volume 1716.13(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3384 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 26.3146 _cell_measurement_theta_min 2.9406 _exptl_absorpt_coefficient_mu 1.581 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.99346 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.575 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_unetI/netI 0.0428 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 7781 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.95 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -7.00 19.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -17.1323 -99.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -17.00 34.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.7104 -57.0000 -150.0000 51 #__ type_ start__ end____ width___ exp.time_ 3 omega -36.00 25.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.7104 -57.0000 0.0000 61 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 50.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 19.7104 -77.0000 150.0000 99 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0132329000 _diffrn_orient_matrix_UB_12 0.0558055000 _diffrn_orient_matrix_UB_13 0.0245443000 _diffrn_orient_matrix_UB_21 0.0073819000 _diffrn_orient_matrix_UB_22 -0.0527178000 _diffrn_orient_matrix_UB_23 0.0265430000 _diffrn_orient_matrix_UB_31 0.0721518000 _diffrn_orient_matrix_UB_32 -0.0047960000 _diffrn_orient_matrix_UB_33 -0.0062118000 _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 4647 _reflns_number_total 5396 _reflns_odcompleteness_completeness 99.79 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _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 0.296 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.055 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.021(12) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 427 _refine_ls_number_reflns 5396 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0344 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.0691 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H20 of C20, H22 of C22, H19 of C19, {H14A,H14B} of C14, H21 of C21, H25 of C25, H29 of C29, {H16A,H16B} of C16, {H12A,H12B} of C12, H32 of C32, H26 of C26, H24 of C24, H27 of C27, H23 of C23, H30 of C30, H28 of C28, H18 of C18, H31 of C31 At 1.5 times of: {H13A,H13B,H13C} of C13, {H15A,H15B,H15C} of C15, {H17A,H17B,H17C} of C17 2.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B) 2.b Aromatic/amide H refined with riding coordinates: C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32) 2.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C) ; _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 -0.01039(4) 0.18854(6) 0.39962(2) 0.04032(13) Uani 1 1 d . . . Cu2 Cu 0.04057(4) 0.19826(7) 0.10463(2) 0.03991(13) Uani 1 1 d . . . S1 S 0.43205(12) 0.39125(16) 0.36953(7) 0.0608(3) Uani 1 1 d . . . S2 S -0.18230(10) 0.36128(14) 0.43496(5) 0.0472(3) Uani 1 1 d . . . S3 S -0.13409(12) 0.04470(15) 0.31863(5) 0.0555(3) Uani 1 1 d . . . S4 S 0.49298(11) 0.39674(15) 0.10762(7) 0.0549(3) Uani 1 1 d . . . S5 S -0.13760(9) 0.37909(13) 0.08078(5) 0.0395(3) Uani 1 1 d . . . N1 N 0.1595(4) 0.2881(4) 0.37206(17) 0.0476(9) Uani 1 1 d . . . N2 N -0.0376(3) 0.5557(4) 0.52066(15) 0.0429(9) Uani 1 1 d . . . N3 N -0.0275(4) 0.1071(4) 0.18976(17) 0.0553(11) Uani 1 1 d . . . N4 N 0.2194(3) 0.3005(4) 0.11675(17) 0.0460(9) Uani 1 1 d . . . N5 N -0.0518(3) 0.5603(4) -0.02530(15) 0.0380(8) Uani 1 1 d . . . N6 N 0.5250(3) 0.4111(4) 0.59793(13) 0.0306(7) Uani 1 1 d . . . N7 N 1.0619(3) 0.0702(4) 0.75526(13) 0.0288(7) Uani 1 1 d . . . N8 N 0.5045(3) 0.4111(4) 0.90582(13) 0.0286(7) Uani 1 1 d . . . C1 C 0.2714(4) 0.3334(5) 0.37076(19) 0.0398(10) Uani 1 1 d . . . C2 C -0.0940(4) 0.4750(5) 0.48486(17) 0.0314(9) Uani 1 1 d . . . C3 C -0.0684(4) 0.0822(5) 0.24309(19) 0.0393(10) Uani 1 1 d . . . C4 C 0.3316(4) 0.3435(4) 0.11329(19) 0.0367(9) Uani 1 1 d . . . C5 C -0.0834(3) 0.4838(4) 0.01823(17) 0.0266(8) Uani 1 1 d . . . C6 C 0.7023(3) 0.3778(4) 0.69471(16) 0.0277(8) Uani 1 1 d . . . C7 C 0.7914(3) 0.2582(4) 0.69613(17) 0.0293(8) Uani 1 1 d . . . C8 C 0.8266(3) 0.1949(5) 0.75982(15) 0.0280(7) Uani 1 1 d . . . C9 C 0.7823(3) 0.2555(4) 0.82257(16) 0.0269(8) Uani 1 1 d . . . C10 C 0.6932(3) 0.3752(4) 0.81980(16) 0.0258(8) Uani 1 1 d . . . C11 C 0.6507(3) 0.4348(4) 0.75597(18) 0.0285(8) Uani 1 1 d . . . C12 C 0.6654(4) 0.4531(5) 0.62695(17) 0.0356(9) Uani 1 1 d . . . H12A H 0.6676 0.5571 0.6342 0.043 Uiso 1 1 calc R . . H12B H 0.7351 0.4295 0.5934 0.043 Uiso 1 1 calc R . . C13 C 0.8563(4) 0.2021(6) 0.63032(16) 0.0427(10) Uani 1 1 d . . . H13A H 0.7956 0.2228 0.5914 0.064 Uiso 1 1 calc R . . H13B H 0.8700 0.0992 0.6339 0.064 Uiso 1 1 calc R . . H13C H 0.9442 0.2489 0.6242 0.064 Uiso 1 1 calc R . . C14 C 0.9068(3) 0.0543(5) 0.76168(18) 0.0353(9) Uani 1 1 d . . . H14A H 0.8887 0.0052 0.8049 0.042 Uiso 1 1 calc R . . H14B H 0.8721 -0.0071 0.7244 0.042 Uiso 1 1 calc R . . C15 C 0.8364(3) 0.1931(6) 0.89038(16) 0.0396(9) Uani 1 1 d . . . H15A H 0.7670 0.1312 0.9095 0.059 Uiso 1 1 calc R . . H15B H 0.8574 0.2706 0.9221 0.059 Uiso 1 1 calc R . . H15C H 0.9190 0.1379 0.8826 0.059 Uiso 1 1 calc R . . C16 C 0.6489(3) 0.4465(4) 0.88599(17) 0.0312(9) Uani 1 1 d . . . H16A H 0.7123 0.4171 0.9232 0.037 Uiso 1 1 calc R . . H16B H 0.6569 0.5508 0.8809 0.037 Uiso 1 1 calc R . . C17 C 0.5530(4) 0.5628(5) 0.75329(19) 0.0434(10) Uani 1 1 d . . . H17A H 0.6059 0.6509 0.7519 0.065 Uiso 1 1 calc R . . H17B H 0.4972 0.5626 0.7937 0.065 Uiso 1 1 calc R . . H17C H 0.4939 0.5561 0.7126 0.065 Uiso 1 1 calc R . . C18 C 0.4415(4) 0.5133(5) 0.57058(17) 0.0371(9) Uani 1 1 d . . . H18 H 0.4707 0.6095 0.5707 0.045 Uiso 1 1 calc R . . C19 C 0.3139(4) 0.4787(6) 0.54251(18) 0.0441(11) Uani 1 1 d . . . H19 H 0.2566 0.5504 0.5236 0.053 Uiso 1 1 calc R . . C20 C 0.2715(4) 0.3362(6) 0.5426(2) 0.0473(12) Uani 1 1 d . . . H20 H 0.1846 0.3108 0.5243 0.057 Uiso 1 1 calc R . . C21 C 0.3582(4) 0.2320(5) 0.57000(19) 0.0489(12) Uani 1 1 d . . . H21 H 0.3313 0.1351 0.5698 0.059 Uiso 1 1 calc R . . C22 C 0.4856(4) 0.2723(5) 0.59789(19) 0.0402(10) Uani 1 1 d . . . H22 H 0.5447 0.2022 0.6168 0.048 Uiso 1 1 calc R . . C23 C 1.1244(4) 0.1968(6) 0.76285(18) 0.0446(9) Uani 1 1 d . . . H23 H 1.0718 0.2794 0.7709 0.054 Uiso 1 1 calc R . . C24 C 1.2679(4) 0.2078(7) 0.75889(19) 0.0544(12) Uani 1 1 d . . . H24 H 1.3121 0.2973 0.7624 0.065 Uiso 1 1 calc R . . C25 C 1.3428(4) 0.0825(7) 0.7496(2) 0.0575(15) Uani 1 1 d . . . H25 H 1.4393 0.0867 0.7485 0.069 Uiso 1 1 calc R . . C26 C 1.2781(5) -0.0461(6) 0.7421(2) 0.0554(13) Uani 1 1 d . . . H26 H 1.3288 -0.1306 0.7354 0.066 Uiso 1 1 calc R . . C27 C 1.1344(5) -0.0503(5) 0.74463(19) 0.0468(11) Uani 1 1 d . . . H27 H 1.0882 -0.1382 0.7388 0.056 Uiso 1 1 calc R . . C28 C 0.4680(4) 0.2729(4) 0.91321(19) 0.0358(9) Uani 1 1 d . . . H28 H 0.5315 0.2001 0.9036 0.043 Uiso 1 1 calc R . . C29 C 0.3371(4) 0.2360(5) 0.9349(2) 0.0464(11) Uani 1 1 d . . . H29 H 0.3132 0.1392 0.9410 0.056 Uiso 1 1 calc R . . C30 C 0.2425(4) 0.3441(6) 0.9475(2) 0.0472(12) Uani 1 1 d . . . H30 H 0.1532 0.3213 0.9612 0.057 Uiso 1 1 calc R . . C31 C 0.2817(4) 0.4853(5) 0.93975(19) 0.0440(11) Uani 1 1 d . . . H31 H 0.2189 0.5595 0.9480 0.053 Uiso 1 1 calc R . . C32 C 0.4134(4) 0.5176(5) 0.91977(18) 0.0383(10) Uani 1 1 d . . . H32 H 0.4404 0.6140 0.9158 0.046 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 0.0451(3) 0.0383(3) 0.0374(2) 0.0042(3) -0.00129(19) -0.0020(3) Cu2 0.0417(2) 0.0439(3) 0.0344(2) -0.0017(3) 0.00566(18) -0.0036(3) S1 0.0527(7) 0.0423(8) 0.0888(9) -0.0116(7) 0.0290(6) -0.0119(6) S2 0.0440(6) 0.0427(8) 0.0540(6) -0.0171(6) -0.0158(5) 0.0079(5) S3 0.0856(8) 0.0495(8) 0.0319(5) -0.0079(5) 0.0111(5) -0.0283(7) S4 0.0389(6) 0.0363(8) 0.0889(9) 0.0038(7) -0.0109(5) -0.0071(6) S5 0.0370(5) 0.0408(7) 0.0411(5) 0.0100(5) 0.0114(4) 0.0053(5) N1 0.047(2) 0.040(3) 0.056(2) 0.0098(18) 0.0105(17) -0.0011(19) N2 0.0450(19) 0.046(3) 0.0374(18) -0.0112(18) -0.0001(15) -0.0035(18) N3 0.084(3) 0.050(3) 0.032(2) 0.0105(17) 0.0131(18) 0.006(2) N4 0.042(2) 0.035(2) 0.060(2) -0.0076(18) -0.0057(17) 0.0018(18) N5 0.0346(17) 0.044(2) 0.0357(17) 0.0041(17) 0.0042(13) -0.0008(16) N6 0.0372(17) 0.030(2) 0.0244(15) 0.0066(14) 0.0006(12) -0.0021(15) N7 0.0347(16) 0.026(2) 0.0251(15) 0.0031(14) -0.0011(12) 0.0052(14) N8 0.0283(15) 0.028(2) 0.0293(15) -0.0018(14) 0.0035(12) 0.0005(14) C1 0.058(3) 0.023(2) 0.039(2) 0.0023(18) 0.0117(19) 0.010(2) C2 0.0298(19) 0.039(3) 0.0260(19) -0.0013(18) 0.0026(15) 0.0075(17) C3 0.058(2) 0.024(2) 0.037(2) -0.0081(18) -0.0007(19) -0.0013(19) C4 0.043(2) 0.019(2) 0.048(2) -0.0074(18) -0.0083(18) 0.0047(19) C5 0.0186(16) 0.033(2) 0.0279(18) -0.0049(17) -0.0016(14) 0.0007(15) C6 0.0251(17) 0.029(2) 0.0291(17) 0.0046(17) -0.0014(13) -0.0065(17) C7 0.0258(18) 0.031(2) 0.0316(19) 0.0011(16) 0.0012(14) -0.0033(16) C8 0.0242(15) 0.027(2) 0.0329(17) -0.002(2) -0.0012(12) -0.0022(19) C9 0.0224(17) 0.029(2) 0.0294(18) 0.0024(15) -0.0007(14) -0.0077(15) C10 0.0232(16) 0.024(2) 0.0297(17) -0.0044(16) 0.0017(13) -0.0049(16) C11 0.0260(18) 0.022(2) 0.038(2) 0.0037(16) -0.0048(15) -0.0063(15) C12 0.037(2) 0.037(3) 0.033(2) 0.0087(18) -0.0001(16) -0.0118(17) C13 0.051(2) 0.045(3) 0.0324(18) -0.004(2) 0.0063(15) 0.000(2) C14 0.037(2) 0.031(3) 0.039(2) 0.0035(18) 0.0009(16) -0.0026(18) C15 0.045(2) 0.040(2) 0.0334(18) 0.001(2) -0.0034(14) 0.004(2) C16 0.0320(19) 0.027(2) 0.034(2) -0.0019(17) 0.0033(15) -0.0068(16) C17 0.051(2) 0.034(3) 0.045(2) 0.006(2) -0.0012(18) 0.005(2) C18 0.051(2) 0.029(3) 0.0313(19) 0.0010(18) 0.0013(17) 0.0084(19) C19 0.042(2) 0.059(4) 0.031(2) -0.004(2) -0.0007(17) 0.013(2) C20 0.041(2) 0.064(4) 0.036(2) -0.007(2) -0.0081(17) -0.002(2) C21 0.054(2) 0.039(3) 0.053(2) 0.000(2) -0.0092(19) -0.013(2) C22 0.044(2) 0.033(3) 0.044(2) 0.0070(19) -0.0088(18) -0.0001(19) C23 0.039(2) 0.033(3) 0.062(2) 0.005(3) -0.0027(17) -0.001(2) C24 0.038(2) 0.055(4) 0.071(3) 0.012(3) -0.0005(19) 0.002(3) C25 0.036(2) 0.096(5) 0.040(2) 0.014(3) 0.0022(18) 0.017(3) C26 0.051(3) 0.059(4) 0.056(3) 0.000(3) 0.009(2) 0.023(3) C27 0.064(3) 0.033(3) 0.043(2) -0.001(2) 0.006(2) 0.013(2) C28 0.033(2) 0.022(2) 0.054(2) -0.0012(18) 0.0090(17) 0.0023(17) C29 0.046(2) 0.032(3) 0.061(3) -0.003(2) 0.0163(19) -0.0063(19) C30 0.034(2) 0.059(4) 0.050(2) -0.004(2) 0.0083(18) -0.004(2) C31 0.035(2) 0.043(3) 0.054(3) -0.002(2) 0.0085(18) 0.014(2) C32 0.044(2) 0.027(3) 0.043(2) -0.0014(19) 0.0000(18) 0.0040(19) _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 S2 2.4091(12) . ? Cu1 S3 2.3518(12) . ? Cu1 N1 1.962(4) . ? Cu1 N2 2.013(3) 2_546 ? Cu2 S5 2.4275(12) . ? Cu2 N3 1.976(3) . ? Cu2 N4 1.971(4) . ? Cu2 N5 1.998(3) 2_545 ? S1 C1 1.637(5) . ? S2 C2 1.646(4) . ? S3 C3 1.644(4) . ? S4 C4 1.636(4) . ? S5 C5 1.644(4) . ? N1 C1 1.157(5) . ? N2 Cu1 2.013(3) 2_556 ? N2 C2 1.144(5) . ? N3 C3 1.137(4) . ? N4 C4 1.155(5) . ? N5 Cu2 1.998(3) 2 ? N5 C5 1.146(4) . ? N6 C12 1.500(4) . ? N6 C18 1.338(5) . ? N6 C22 1.335(5) . ? N7 C14 1.508(4) . ? N7 C23 1.320(6) . ? N7 C27 1.331(5) . ? N8 C16 1.488(4) . ? N8 C28 1.330(5) . ? N8 C32 1.348(5) . ? C6 C7 1.397(5) . ? C6 C11 1.399(5) . ? C6 C12 1.517(5) . ? C7 C8 1.396(5) . ? C7 C13 1.523(5) . ? C8 C9 1.412(4) . ? C8 C14 1.509(6) . ? C9 C10 1.398(5) . ? C9 C15 1.512(5) . ? C10 C11 1.402(5) . ? C10 C16 1.511(4) . ? C11 C17 1.509(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18 0.9300 . ? C18 C19 1.368(5) . ? C19 H19 0.9300 . ? C19 C20 1.376(7) . ? C20 H20 0.9300 . ? C20 C21 1.369(6) . ? C21 H21 0.9300 . ? C21 C22 1.378(5) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C23 C24 1.390(5) . ? C24 H24 0.9300 . ? C24 C25 1.376(7) . ? C25 H25 0.9300 . ? C25 C26 1.346(7) . ? C26 H26 0.9300 . ? C26 C27 1.386(6) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C28 C29 1.381(5) . ? C29 H29 0.9300 . ? C29 C30 1.376(6) . ? C30 H30 0.9300 . ? C30 C31 1.365(7) . ? C31 H31 0.9300 . ? C31 C32 1.369(5) . ? C32 H32 0.9300 . ? 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 S3 Cu1 S2 102.84(4) . . ? N1 Cu1 S2 110.61(12) . . ? N1 Cu1 S3 119.60(11) . . ? N1 Cu1 N2 108.47(14) . 2_546 ? N2 Cu1 S2 109.28(10) 2_546 . ? N2 Cu1 S3 105.59(12) 2_546 . ? N3 Cu2 S5 101.66(11) . . ? N3 Cu2 N5 113.27(16) . 2_545 ? N4 Cu2 S5 107.72(11) . . ? N4 Cu2 N3 114.36(15) . . ? N4 Cu2 N5 109.33(13) . 2_545 ? N5 Cu2 S5 110.10(9) 2_545 . ? C2 S2 Cu1 103.87(13) . . ? C3 S3 Cu1 105.85(15) . . ? C5 S5 Cu2 107.85(12) . . ? C1 N1 Cu1 163.5(3) . . ? C2 N2 Cu1 162.7(3) . 2_556 ? C3 N3 Cu2 166.4(4) . . ? C4 N4 Cu2 166.6(3) . . ? C5 N5 Cu2 167.7(3) . 2 ? C18 N6 C12 119.5(4) . . ? C22 N6 C12 120.0(3) . . ? C22 N6 C18 120.5(3) . . ? C23 N7 C14 121.7(3) . . ? C23 N7 C27 121.1(4) . . ? C27 N7 C14 117.2(4) . . ? C28 N8 C16 119.3(3) . . ? C28 N8 C32 120.1(3) . . ? C32 N8 C16 120.6(3) . . ? N1 C1 S1 177.8(4) . . ? N2 C2 S2 177.3(4) . . ? N3 C3 S3 177.5(4) . . ? N4 C4 S4 177.3(4) . . ? N5 C5 S5 176.6(3) . . ? C7 C6 C11 120.8(3) . . ? C7 C6 C12 120.5(3) . . ? C11 C6 C12 118.6(3) . . ? C6 C7 C13 121.1(3) . . ? C8 C7 C6 118.8(3) . . ? C8 C7 C13 120.0(3) . . ? C7 C8 C9 121.4(4) . . ? C7 C8 C14 119.5(3) . . ? C9 C8 C14 119.1(3) . . ? C8 C9 C15 119.3(3) . . ? C10 C9 C8 118.6(3) . . ? C10 C9 C15 122.0(3) . . ? C9 C10 C11 120.5(3) . . ? C9 C10 C16 119.9(3) . . ? C11 C10 C16 119.5(3) . . ? C6 C11 C10 119.7(3) . . ? C6 C11 C17 120.0(3) . . ? C10 C11 C17 120.2(3) . . ? N6 C12 C6 113.2(3) . . ? N6 C12 H12A 108.9 . . ? N6 C12 H12B 108.9 . . ? C6 C12 H12A 108.9 . . ? C6 C12 H12B 108.9 . . ? H12A C12 H12B 107.8 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N7 C14 C8 115.0(3) . . ? N7 C14 H14A 108.5 . . ? N7 C14 H14B 108.5 . . ? C8 C14 H14A 108.5 . . ? C8 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N8 C16 C10 114.2(3) . . ? N8 C16 H16A 108.7 . . ? N8 C16 H16B 108.7 . . ? C10 C16 H16A 108.7 . . ? C10 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 H18 119.5 . . ? N6 C18 C19 121.1(4) . . ? C19 C18 H18 119.5 . . ? C18 C19 H19 120.5 . . ? C18 C19 C20 119.0(4) . . ? C20 C19 H19 120.5 . . ? C19 C20 H20 120.2 . . ? C21 C20 C19 119.5(4) . . ? C21 C20 H20 120.2 . . ? C20 C21 H21 120.4 . . ? C20 C21 C22 119.3(5) . . ? C22 C21 H21 120.4 . . ? N6 C22 C21 120.5(4) . . ? N6 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? N7 C23 H23 119.7 . . ? N7 C23 C24 120.6(5) . . ? C24 C23 H23 119.7 . . ? C23 C24 H24 121.0 . . ? C25 C24 C23 118.1(5) . . ? C25 C24 H24 121.0 . . ? C24 C25 H25 119.6 . . ? C26 C25 C24 120.8(4) . . ? C26 C25 H25 119.6 . . ? C25 C26 H26 120.6 . . ? C25 C26 C27 118.7(5) . . ? C27 C26 H26 120.6 . . ? N7 C27 C26 120.7(5) . . ? N7 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? N8 C28 H28 119.5 . . ? N8 C28 C29 120.9(4) . . ? C29 C28 H28 119.5 . . ? C28 C29 H29 120.4 . . ? C30 C29 C28 119.3(4) . . ? C30 C29 H29 120.4 . . ? C29 C30 H30 120.5 . . ? C31 C30 C29 119.0(4) . . ? C31 C30 H30 120.5 . . ? C30 C31 H31 120.0 . . ? C30 C31 C32 120.0(4) . . ? C32 C31 H31 120.0 . . ? N8 C32 C31 120.7(4) . . ? N8 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? _database_code_depnum_ccdc_archive 'CCDC 926422' ####################################################################### # # 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_1 #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C76 H60 Cu8 N24 O0 S16' _chemical_formula_weight 2330.76 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.190(4) _cell_length_b 20.588(9) _cell_length_c 24.602(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4655(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1124 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 18.67 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2344 _exptl_absorpt_coefficient_mu 2.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6545 _exptl_absorpt_correction_T_max 0.6667 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24787 _diffrn_reflns_av_R_equivalents 0.1739 _diffrn_reflns_av_sigmaI/netI 0.1213 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4096 _reflns_number_gt 1871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0383P)^2^+0.9548P] 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 4096 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1654 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.18064(10) 1.06317(4) 0.17078(4) 0.0475(3) Uani 1 1 d . . . Cu2 Cu 0.23095(12) 0.81589(5) 0.07888(4) 0.0641(4) Uani 1 1 d . . . N1 N 0.2290(6) 1.1572(3) 0.1714(3) 0.0473(17) Uani 1 1 d . . . N2 N 0.2177(7) 0.9102(3) 0.0693(3) 0.057(2) Uani 1 1 d . . . N3 N 0.3599(7) 0.7632(3) 0.0335(3) 0.061(2) Uani 1 1 d . . . N4 N 0.3026(6) 0.3871(3) 0.4051(2) 0.0329(15) Uani 1 1 d . . . N5 N 0.6133(6) 0.3717(2) 0.6008(2) 0.0285(14) Uani 1 1 d . . . N6 N 0.0354(7) 1.0427(3) 0.2274(3) 0.0559(19) Uani 1 1 d . . . S1 S 0.1109(2) 1.03692(9) 0.07875(8) 0.0449(5) Uani 1 1 d . . . S2 S 0.2627(3) 1.29221(10) 0.17163(8) 0.0637(7) Uani 1 1 d . . . S3 S -0.0273(3) 0.78566(11) 0.06301(11) 0.0789(8) Uani 1 1 d . . . S6 S 0.3826(2) 0.99255(10) 0.18312(8) 0.0484(6) Uani 1 1 d . . . C1 C 0.1769(8) 0.9626(4) 0.0734(3) 0.0391(19) Uani 1 1 d . . . C2 C 0.2436(7) 1.2129(4) 0.1706(3) 0.041(2) Uani 1 1 d . . . C3 C 0.4713(8) 1.0226(3) 0.2363(3) 0.041(2) Uani 1 1 d . . . C4 C -0.0891(8) 0.7573(4) 0.0047(4) 0.046(2) Uani 1 1 d . . . C5 C 0.3887(8) 0.3582(4) 0.3680(3) 0.051(2) Uani 1 1 d . . . H5 H 0.4759 0.3387 0.3782 0.061 Uiso 1 1 calc R . . C6 C 0.3433(10) 0.3583(4) 0.3143(3) 0.062(3) Uani 1 1 d . . . H6 H 0.3993 0.3380 0.2878 0.074 Uiso 1 1 calc R . . C7 C 0.2178(11) 0.3881(4) 0.3004(4) 0.069(3) Uani 1 1 d . . . H7 H 0.1872 0.3877 0.2644 0.083 Uiso 1 1 calc R . . C8 C 0.1358(9) 0.4186(4) 0.3385(4) 0.068(3) Uani 1 1 d . . . H8 H 0.0511 0.4404 0.3287 0.081 Uiso 1 1 calc R . . C9 C 0.1794(8) 0.4170(3) 0.3910(3) 0.044(2) Uani 1 1 d . . . H9 H 0.1229 0.4369 0.4176 0.053 Uiso 1 1 calc R . . C10 C 0.7373(9) 0.3628(3) 0.5730(3) 0.044(2) Uani 1 1 d . . . H10 H 0.7405 0.3702 0.5357 0.053 Uiso 1 1 calc R . . C11 C 0.8587(8) 0.3427(4) 0.6002(4) 0.050(2) Uani 1 1 d . . . H11 H 0.9446 0.3350 0.5813 0.060 Uiso 1 1 calc R . . C12 C 0.8542(9) 0.3339(4) 0.6553(4) 0.066(3) Uani 1 1 d . . . H12 H 0.9374 0.3213 0.6740 0.079 Uiso 1 1 calc R . . C13 C 0.7271(10) 0.3437(4) 0.6824(3) 0.069(3) Uani 1 1 d . . . H13 H 0.7232 0.3378 0.7199 0.083 Uiso 1 1 calc R . . C14 C 0.6049(8) 0.3621(3) 0.6546(3) 0.043(2) Uani 1 1 d . . . H14 H 0.5172 0.3680 0.6728 0.051 Uiso 1 1 calc R . . C15 C 0.4764(7) 0.3885(3) 0.5713(3) 0.0370(19) Uani 1 1 d . . . H15A H 0.4014 0.3983 0.5978 0.044 Uiso 1 1 calc R . . H15B H 0.4447 0.3508 0.5508 0.044 Uiso 1 1 calc R . . C16 C 0.4914(7) 0.4455(3) 0.5329(3) 0.0283(17) Uani 1 1 d . . . C17 C 0.5618(7) 0.5006(3) 0.5505(3) 0.0351(18) Uani 1 1 d . . . H17 H 0.6030 0.5010 0.5850 0.042 Uiso 1 1 calc R . . C18 C 0.4273(7) 0.4447(3) 0.4817(3) 0.0309(17) Uani 1 1 d . . . C19 C 0.3457(8) 0.3849(3) 0.4628(3) 0.047(2) Uani 1 1 d . . . H19A H 0.4066 0.3470 0.4686 0.056 Uiso 1 1 calc R . . H19B H 0.2590 0.3798 0.4849 0.056 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 0.0482(6) 0.0448(6) 0.0494(6) -0.0004(5) 0.0056(5) -0.0039(5) Cu2 0.0848(9) 0.0470(7) 0.0603(7) 0.0041(6) 0.0095(7) 0.0123(6) N1 0.050(4) 0.044(4) 0.048(4) -0.003(4) 0.005(4) 0.002(3) N2 0.067(5) 0.036(4) 0.066(5) -0.002(4) -0.003(4) -0.007(4) N3 0.055(5) 0.058(5) 0.069(6) -0.002(4) 0.008(4) 0.011(4) N4 0.040(4) 0.027(4) 0.032(4) 0.000(3) -0.009(3) -0.001(3) N5 0.032(4) 0.026(3) 0.028(4) 0.002(3) -0.003(3) 0.002(3) N6 0.056(5) 0.062(5) 0.050(4) -0.003(4) 0.019(4) -0.010(4) S1 0.0465(12) 0.0424(13) 0.0457(12) -0.0016(10) -0.0063(11) 0.0029(10) S2 0.1070(19) 0.0391(14) 0.0451(13) -0.0075(10) 0.0030(14) -0.0086(12) S3 0.0600(17) 0.0680(18) 0.109(2) -0.0357(15) -0.0205(15) 0.0033(13) S6 0.0565(14) 0.0475(14) 0.0412(12) -0.0038(10) -0.0127(11) 0.0094(10) C1 0.033(5) 0.045(5) 0.039(5) -0.003(4) 0.004(4) -0.012(4) C2 0.037(5) 0.061(6) 0.027(4) -0.002(5) 0.005(4) 0.000(4) C3 0.040(5) 0.034(5) 0.050(6) 0.014(4) -0.002(4) 0.005(4) C4 0.029(5) 0.025(5) 0.084(7) 0.004(4) -0.002(5) 0.002(4) C5 0.036(5) 0.057(6) 0.060(6) -0.008(5) -0.007(5) 0.006(4) C6 0.067(7) 0.065(7) 0.054(6) -0.021(5) 0.017(5) -0.002(5) C7 0.089(8) 0.072(7) 0.047(6) 0.003(5) -0.025(6) 0.004(6) C8 0.057(6) 0.068(7) 0.079(7) 0.012(6) -0.030(6) 0.010(5) C9 0.044(5) 0.042(5) 0.047(5) 0.002(4) -0.002(4) 0.014(4) C10 0.050(6) 0.045(5) 0.038(5) -0.011(4) 0.017(5) -0.007(4) C11 0.025(5) 0.045(5) 0.079(7) -0.015(5) 0.009(5) -0.002(4) C12 0.049(6) 0.065(7) 0.084(8) 0.011(5) -0.033(5) 0.006(5) C13 0.060(6) 0.108(8) 0.039(5) 0.011(5) -0.013(5) 0.010(6) C14 0.048(5) 0.053(5) 0.028(5) 0.008(4) 0.004(4) 0.002(4) C15 0.031(5) 0.038(5) 0.041(5) 0.006(4) -0.006(4) -0.005(3) C16 0.024(4) 0.029(5) 0.032(4) 0.004(3) 0.006(3) 0.004(3) C17 0.045(5) 0.035(5) 0.025(4) -0.005(4) 0.002(4) 0.002(4) C18 0.030(4) 0.028(5) 0.034(4) -0.002(4) -0.002(3) -0.005(3) C19 0.062(6) 0.040(5) 0.038(5) 0.004(4) -0.013(4) -0.005(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 N6 1.975(6) . ? Cu1 N1 1.986(7) . ? Cu1 S6 2.377(2) . ? Cu1 S1 2.414(2) . ? Cu2 N3 1.957(7) . ? Cu2 N2 1.961(7) . ? Cu2 S2 2.334(2) 7_655 ? Cu2 S3 2.484(3) . ? N1 C2 1.155(8) . ? N2 C1 1.145(8) . ? N3 C4 1.131(9) 3_565 ? N4 C9 1.335(8) . ? N4 C5 1.346(8) . ? N4 C19 1.473(8) . ? N5 C10 1.341(8) . ? N5 C14 1.342(7) . ? N5 C15 1.492(7) . ? N6 C3 1.147(8) 6_556 ? S1 C1 1.652(8) . ? S2 C2 1.643(9) . ? S2 Cu2 2.334(2) 7_665 ? S3 C4 1.650(9) . ? S6 C3 1.661(8) . ? C3 N6 1.147(8) 6_656 ? C4 N3 1.131(9) 3_465 ? C5 C6 1.387(10) . ? C5 H5 0.9300 . ? C6 C7 1.350(10) . ? C6 H6 0.9300 . ? C7 C8 1.357(11) . ? C7 H7 0.9300 . ? C8 C9 1.354(10) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.365(9) . ? C10 H10 0.9300 . ? C11 C12 1.367(10) . ? C11 H11 0.9300 . ? C12 C13 1.361(10) . ? C12 H12 0.9300 . ? C13 C14 1.368(9) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.514(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.376(8) . ? C16 C18 1.390(8) . ? C17 C18 1.381(8) 5_666 ? C17 H17 0.9300 . ? C18 C17 1.381(8) 5_666 ? C18 C19 1.516(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Cu1 N1 110.7(3) . . ? N6 Cu1 S6 107.9(2) . . ? N1 Cu1 S6 114.86(18) . . ? N6 Cu1 S1 115.7(2) . . ? N1 Cu1 S1 106.56(19) . . ? S6 Cu1 S1 100.96(7) . . ? N3 Cu2 N2 121.2(3) . . ? N3 Cu2 S2 115.3(2) . 7_655 ? N2 Cu2 S2 109.0(2) . 7_655 ? N3 Cu2 S3 110.5(2) . . ? N2 Cu2 S3 99.8(2) . . ? S2 Cu2 S3 97.19(9) 7_655 . ? C2 N1 Cu1 173.6(6) . . ? C1 N2 Cu2 160.3(7) . . ? C4 N3 Cu2 158.7(7) 3_565 . ? C9 N4 C5 121.8(6) . . ? C9 N4 C19 119.5(6) . . ? C5 N4 C19 118.8(6) . . ? C10 N5 C14 122.1(6) . . ? C10 N5 C15 120.0(6) . . ? C14 N5 C15 117.7(6) . . ? C3 N6 Cu1 166.7(7) 6_556 . ? C1 S1 Cu1 100.6(3) . . ? C2 S2 Cu2 101.3(3) . 7_665 ? C4 S3 Cu2 123.7(3) . . ? C3 S6 Cu1 104.8(3) . . ? N2 C1 S1 177.5(7) . . ? N1 C2 S2 178.1(7) . . ? N6 C3 S6 178.5(8) 6_656 . ? N3 C4 S3 175.3(8) 3_465 . ? N4 C5 C6 118.0(7) . . ? N4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C7 C6 C5 119.9(8) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.7(8) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 118.9(8) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? N4 C9 C8 120.7(7) . . ? N4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? N5 C10 C11 119.1(7) . . ? N5 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C12 120.1(7) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.5(8) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.0(8) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? N5 C14 C13 119.1(7) . . ? N5 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? N5 C15 C16 114.0(5) . . ? N5 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? N5 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C18 119.6(6) . . ? C17 C16 C15 119.0(6) . . ? C18 C16 C15 121.2(6) . . ? C16 C17 C18 121.7(6) . 5_666 ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 5_666 . ? C17 C18 C16 118.7(6) 5_666 . ? C17 C18 C19 121.5(6) 5_666 . ? C16 C18 C19 119.8(6) . . ? N4 C19 C18 113.8(5) . . ? N4 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? N4 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? 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 N6 Cu1 N1 C2 -62(6) . . . . ? S6 Cu1 N1 C2 176(6) . . . . ? S1 Cu1 N1 C2 65(6) . . . . ? N3 Cu2 N2 C1 169.0(19) . . . . ? S2 Cu2 N2 C1 -53(2) 7_655 . . . ? S3 Cu2 N2 C1 48(2) . . . . ? N2 Cu2 N3 C4 -53(2) . . . 3_565 ? S2 Cu2 N3 C4 172.0(19) 7_655 . . 3_565 ? S3 Cu2 N3 C4 63(2) . . . 3_565 ? N1 Cu1 N6 C3 -123(3) . . . 6_556 ? S6 Cu1 N6 C3 4(3) . . . 6_556 ? S1 Cu1 N6 C3 116(3) . . . 6_556 ? N6 Cu1 S1 C1 -91.7(3) . . . . ? N1 Cu1 S1 C1 144.7(3) . . . . ? S6 Cu1 S1 C1 24.4(3) . . . . ? N3 Cu2 S3 C4 -29.6(4) . . . . ? N2 Cu2 S3 C4 99.2(4) . . . . ? S2 Cu2 S3 C4 -150.0(3) 7_655 . . . ? N6 Cu1 S6 C3 -76.0(4) . . . . ? N1 Cu1 S6 C3 48.0(3) . . . . ? S1 Cu1 S6 C3 162.2(3) . . . . ? Cu2 N2 C1 S1 -51(19) . . . . ? Cu1 S1 C1 N2 123(18) . . . . ? Cu1 N1 C2 S2 87(24) . . . . ? Cu2 S2 C2 N1 -164(22) 7_665 . . . ? Cu1 S6 C3 N6 -154(29) . . . 6_656 ? Cu2 S3 C4 N3 169(9) . . . 3_465 ? C9 N4 C5 C6 -2.1(11) . . . . ? C19 N4 C5 C6 177.3(6) . . . . ? N4 C5 C6 C7 1.4(12) . . . . ? C5 C6 C7 C8 0.7(13) . . . . ? C6 C7 C8 C9 -2.2(13) . . . . ? C5 N4 C9 C8 0.7(11) . . . . ? C19 N4 C9 C8 -178.7(7) . . . . ? C7 C8 C9 N4 1.5(12) . . . . ? C14 N5 C10 C11 0.7(10) . . . . ? C15 N5 C10 C11 -175.1(6) . . . . ? N5 C10 C11 C12 -2.1(11) . . . . ? C10 C11 C12 C13 1.6(12) . . . . ? C11 C12 C13 C14 0.1(13) . . . . ? C10 N5 C14 C13 1.0(10) . . . . ? C15 N5 C14 C13 177.0(6) . . . . ? C12 C13 C14 N5 -1.4(12) . . . . ? C10 N5 C15 C16 -51.4(8) . . . . ? C14 N5 C15 C16 132.5(6) . . . . ? N5 C15 C16 C17 -46.0(8) . . . . ? N5 C15 C16 C18 138.4(6) . . . . ? C18 C16 C17 C18 -1.1(11) . . . 5_666 ? C15 C16 C17 C18 -176.8(6) . . . 5_666 ? C17 C16 C18 C17 1.0(10) . . . 5_666 ? C15 C16 C18 C17 176.7(6) . . . 5_666 ? C17 C16 C18 C19 -178.1(6) . . . . ? C15 C16 C18 C19 -2.5(9) . . . . ? C9 N4 C19 C18 -84.7(8) . . . . ? C5 N4 C19 C18 95.9(7) . . . . ? C17 C18 C19 N4 9.5(9) 5_666 . . . ? C16 C18 C19 N4 -171.3(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.505 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 926179'