# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'G Bowmaker' _publ_contact_author_email G.BOWMAKER@AUCKLAND.AC.NZ _publ_section_title ; Spectroscopy and structures of two complete families, one mononuclear, the other binuclear, of 1:2 CuX : dptu stoichiometry (X = Cl, Br, I; 'dptu' = N,N'-diphenylthiourea) ; loop_ _publ_author_name 'G Bowmaker' 'Narongsak Chaichit' 'John V. Hanna' 'Chaveng Pakawatchai' 'Brian W Skelton' ; A.H.White ; # Attachment 'gb0713_paper.cif' data_gb0713 _database_code_depnum_ccdc_archive 'CCDC 660459' _audit_creation_date 2007-11-13T13:59:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C26 H26 Cl Cu N4 O S2' _chemical_formula_moiety 'C26 H24 Cl Cu N4 S2, H2 O' _chemical_formula_weight 573.62 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4076(5) _cell_length_b 12.0075(6) _cell_length_c 12.6204(4) _cell_angle_alpha 89.217(3) _cell_angle_beta 73.998(3) _cell_angle_gamma 69.361(4) _cell_volume 1276.89(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6988 _cell_measurement_theta_min 2.4363 _cell_measurement_theta_max 34.5188 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.98724 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0009 _diffrn_orient_matrix_ub_11 0.046103005 _diffrn_orient_matrix_ub_12 0.0336701296 _diffrn_orient_matrix_ub_13 0.0062789101 _diffrn_orient_matrix_ub_21 -0.0688406624 _diffrn_orient_matrix_ub_22 0.0526979109 _diffrn_orient_matrix_ub_23 0.0132603698 _diffrn_orient_matrix_ub_31 -0.0142026137 _diffrn_orient_matrix_ub_32 -0.0099978051 _diffrn_orient_matrix_ub_33 0.0567823956 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_unetI/netI 0.1557 _diffrn_reflns_number 24509 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 34.6 _diffrn_reflns_theta_full 33.75 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.931 _reflns_number_total 10140 _reflns_number_gt 5615 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0389P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 10140 _refine_ls_number_parameters 324 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.844 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.635 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.1 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.44524(3) 0.60733(2) 0.266849(19) 0.01576(7) Uani 1 1 d . . . Cl1 Cl 0.33350(6) 0.80493(5) 0.30475(4) 0.01866(11) Uani 1 1 d . . . S1 S 0.62934(6) 0.50751(5) 0.11549(4) 0.01505(10) Uani 1 1 d . . . C1 C 0.6462(2) 0.59869(18) 0.01090(15) 0.0141(4) Uani 1 1 d . . . N11 N 0.75808(18) 0.55666(15) -0.08602(12) 0.0140(3) Uani 1 1 d . . . H11 H 0.7628 0.6053 -0.1385 0.017 Uiso 1 1 calc R . . C111 C 0.8704(2) 0.43650(18) -0.10855(15) 0.0130(4) Uani 1 1 d . . . C112 C 1.0308(2) 0.4162(2) -0.12937(15) 0.0176(4) Uani 1 1 d . . . H112 H 1.0657 0.4815 -0.129 0.021 Uiso 1 1 calc R . . C113 C 1.1396(2) 0.2998(2) -0.15073(16) 0.0203(4) Uani 1 1 d . . . H113 H 1.2497 0.2853 -0.1669 0.024 Uiso 1 1 calc R . . C114 C 1.0888(3) 0.20438(19) -0.14858(16) 0.0213(5) Uani 1 1 d . . . H114 H 1.1633 0.1247 -0.1608 0.026 Uiso 1 1 calc R . . C115 C 0.9281(3) 0.2258(2) -0.12845(16) 0.0209(4) Uani 1 1 d . . . H115 H 0.8929 0.1607 -0.1276 0.025 Uiso 1 1 calc R . . C116 C 0.8190(2) 0.34193(18) -0.10961(15) 0.0162(4) Uani 1 1 d . . . H116 H 0.7095 0.3565 -0.0975 0.019 Uiso 1 1 calc R . . N12 N 0.54865(18) 0.71248(15) 0.02429(13) 0.0147(3) Uani 1 1 d . . . H12 H 0.485 0.7419 0.0911 0.018 Uiso 1 1 calc R . . C121 C 0.5403(2) 0.79094(17) -0.06364(15) 0.0142(4) Uani 1 1 d . . . C122 C 0.4494(2) 0.7871(2) -0.13188(17) 0.0219(5) Uani 1 1 d . . . H122 H 0.3935 0.7336 -0.121 0.026 Uiso 1 1 calc R . . C123 C 0.4407(3) 0.8620(2) -0.21636(18) 0.0256(5) Uani 1 1 d . . . H123 H 0.3783 0.8601 -0.2635 0.031 Uiso 1 1 calc R . . C124 C 0.5219(3) 0.9388(2) -0.23208(17) 0.0247(5) Uani 1 1 d . . . H124 H 0.515 0.9904 -0.2897 0.03 Uiso 1 1 calc R . . C125 C 0.6139(3) 0.9413(2) -0.16401(17) 0.0239(5) Uani 1 1 d . . . H125 H 0.67 0.9946 -0.1751 0.029 Uiso 1 1 calc R . . C126 C 0.6243(2) 0.86632(19) -0.07972(17) 0.0205(4) Uani 1 1 d . . . H126 H 0.6886 0.8669 -0.0336 0.025 Uiso 1 1 calc R . . S2 S 0.38778(6) 0.47541(5) 0.38001(4) 0.01528(10) Uani 1 1 d . . . C2 C 0.2609(2) 0.54991(18) 0.50405(15) 0.0137(4) Uani 1 1 d . . . N21 N 0.17945(18) 0.49687(14) 0.57884(12) 0.0133(3) Uani 1 1 d . . . H21 H 0.1065 0.5423 0.6368 0.016 Uiso 1 1 calc R . . C211 C 0.2017(2) 0.37355(18) 0.57178(14) 0.0127(4) Uani 1 1 d . . . C212 C 0.0692(2) 0.34180(19) 0.59026(15) 0.0156(4) Uani 1 1 d . . . H212 H -0.0337 0.4019 0.6066 0.019 Uiso 1 1 calc R . . C213 C 0.0874(2) 0.22242(19) 0.58487(16) 0.0181(4) Uani 1 1 d . . . H213 H -0.0033 0.2006 0.598 0.022 Uiso 1 1 calc R . . C214 C 0.2368(3) 0.13475(19) 0.56054(16) 0.0210(4) Uani 1 1 d . . . H214 H 0.2493 0.0529 0.5544 0.025 Uiso 1 1 calc R . . C215 C 0.3688(2) 0.16670(19) 0.54510(17) 0.0213(5) Uani 1 1 d . . . H215 H 0.4716 0.1065 0.5297 0.026 Uiso 1 1 calc R . . C216 C 0.3510(2) 0.28589(18) 0.55209(16) 0.0166(4) Uani 1 1 d . . . H216 H 0.4411 0.3076 0.5434 0.02 Uiso 1 1 calc R . . N22 N 0.23606(18) 0.66509(15) 0.52610(13) 0.0140(3) Uani 1 1 d . . . H22 H 0.2726 0.7006 0.4692 0.017 Uiso 1 1 calc R . . C221 C 0.1591(2) 0.73874(17) 0.62818(15) 0.0126(4) Uani 1 1 d . . . C222 C 0.0859(2) 0.86024(19) 0.62343(16) 0.0183(4) Uani 1 1 d . . . H222 H 0.0839 0.8914 0.554 0.022 Uiso 1 1 calc R . . C223 C 0.0153(3) 0.9364(2) 0.72028(17) 0.0218(5) Uani 1 1 d . . . H223 H -0.0333 1.02 0.7173 0.026 Uiso 1 1 calc R . . C224 C 0.0162(2) 0.89001(19) 0.82134(17) 0.0203(4) Uani 1 1 d . . . H224 H -0.0335 0.9419 0.8878 0.024 Uiso 1 1 calc R . . C225 C 0.0884(2) 0.76950(19) 0.82604(16) 0.0167(4) Uani 1 1 d . . . H225 H 0.0878 0.7384 0.8957 0.02 Uiso 1 1 calc R . . C226 C 0.1623(2) 0.69278(18) 0.72939(15) 0.0151(4) Uani 1 1 d . . . H226 H 0.2144 0.6097 0.7326 0.018 Uiso 1 1 calc R . . O1 O 0.15737(18) 0.35127(16) 0.30039(12) 0.0194(3) Uani 1 1 d D . . H1A H 0.214(3) 0.371(2) 0.3272(19) 0.026(7) Uiso 1 1 d D . . H1B H 0.183(3) 0.279(2) 0.303(2) 0.053(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01574(12) 0.01739(14) 0.01256(12) 0.00328(10) -0.00197(9) -0.00581(10) Cl1 0.0204(2) 0.0151(3) 0.0194(2) 0.00515(19) -0.00452(19) -0.0062(2) S1 0.0161(2) 0.0141(3) 0.0119(2) 0.00412(18) -0.00153(18) -0.00380(19) C1 0.0122(9) 0.0173(10) 0.0158(9) 0.0040(8) -0.0061(7) -0.0075(8) N11 0.0156(8) 0.0130(9) 0.0100(7) 0.0029(6) -0.0008(6) -0.0035(7) C111 0.0142(9) 0.0133(10) 0.0084(8) 0.0012(7) -0.0016(7) -0.0026(8) C112 0.0157(9) 0.0234(12) 0.0127(9) 0.0011(8) -0.0028(8) -0.0070(9) C113 0.0141(9) 0.0257(12) 0.0162(10) -0.0024(9) -0.0047(8) -0.0010(9) C114 0.0251(11) 0.0154(11) 0.0132(10) -0.0038(8) -0.0049(8) 0.0044(9) C115 0.0276(11) 0.0184(11) 0.0154(10) -0.0006(8) -0.0044(8) -0.0081(9) C116 0.0158(9) 0.0182(11) 0.0142(9) 0.0010(8) -0.0037(8) -0.0060(8) N12 0.0142(8) 0.0163(9) 0.0104(8) 0.0038(7) -0.0004(6) -0.0041(7) C121 0.0124(9) 0.0122(10) 0.0126(9) 0.0027(7) -0.0003(7) -0.0007(7) C122 0.0209(10) 0.0239(12) 0.0246(11) 0.0092(9) -0.0094(9) -0.0107(9) C123 0.0247(11) 0.0320(14) 0.0229(11) 0.0105(10) -0.0113(9) -0.0105(10) C124 0.0264(11) 0.0230(12) 0.0201(11) 0.0101(9) -0.0046(9) -0.0055(10) C125 0.0279(12) 0.0221(12) 0.0228(11) 0.0069(9) -0.0035(9) -0.0134(10) C126 0.0235(11) 0.0217(12) 0.0190(10) 0.0048(9) -0.0070(9) -0.0107(9) S2 0.0164(2) 0.0148(3) 0.0113(2) 0.00115(18) 0.00051(18) -0.0051(2) C2 0.0148(9) 0.0167(10) 0.0123(9) 0.0046(8) -0.0068(7) -0.0068(8) N21 0.0144(8) 0.0133(9) 0.0095(7) 0.0008(6) -0.0002(6) -0.0041(7) C211 0.0163(9) 0.0150(10) 0.0079(8) 0.0016(7) -0.0029(7) -0.0074(8) C212 0.0138(9) 0.0215(11) 0.0117(9) 0.0046(8) -0.0034(7) -0.0067(8) C213 0.0192(10) 0.0220(12) 0.0166(10) 0.0027(8) -0.0056(8) -0.0112(9) C214 0.0271(11) 0.0131(11) 0.0207(11) -0.0001(8) -0.0028(9) -0.0078(9) C215 0.0167(10) 0.0160(11) 0.0236(11) 0.0033(9) -0.0010(8) -0.0006(8) C216 0.0177(9) 0.0155(11) 0.0165(10) 0.0038(8) -0.0041(8) -0.0068(8) N22 0.0159(8) 0.0129(9) 0.0116(8) 0.0036(6) -0.0017(6) -0.0050(7) C221 0.0111(8) 0.0131(10) 0.0124(9) -0.0002(7) -0.0020(7) -0.0039(7) C222 0.0209(10) 0.0164(11) 0.0154(10) 0.0033(8) -0.0049(8) -0.0044(8) C223 0.0267(11) 0.0131(11) 0.0215(11) 0.0023(8) -0.0074(9) -0.0022(9) C224 0.0227(11) 0.0196(12) 0.0163(10) -0.0024(8) -0.0035(8) -0.0062(9) C225 0.0185(10) 0.0199(11) 0.0124(9) 0.0014(8) -0.0050(8) -0.0074(8) C226 0.0182(9) 0.0117(10) 0.0151(9) 0.0022(8) -0.0052(8) -0.0046(8) O1 0.0196(8) 0.0194(9) 0.0177(8) 0.0025(6) -0.0041(6) -0.0062(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.2046(5) . ? Cu1 S2 2.2264(5) . ? Cu1 Cl1 2.2269(6) . ? S1 C1 1.7128(19) . ? C1 N12 1.332(3) . ? C1 N11 1.338(2) . ? N11 C111 1.432(2) . ? N11 H11 0.88 . ? C111 C116 1.383(3) . ? C111 C112 1.390(3) . ? C112 C113 1.388(3) . ? C112 H112 0.95 . ? C113 C114 1.385(3) . ? C113 H113 0.95 . ? C114 C115 1.390(3) . ? C114 H114 0.95 . ? C115 C116 1.385(3) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? N12 C121 1.447(2) . ? N12 H12 0.88 . ? C121 C126 1.377(3) . ? C121 C122 1.382(3) . ? C122 C123 1.387(3) . ? C122 H122 0.95 . ? C123 C124 1.372(3) . ? C123 H123 0.95 . ? C124 C125 1.385(3) . ? C124 H124 0.95 . ? C125 C126 1.386(3) . ? C125 H125 0.95 . ? C126 H126 0.95 . ? S2 C2 1.712(2) . ? C2 N22 1.339(3) . ? C2 N21 1.346(2) . ? N21 C211 1.421(3) . ? N21 H21 0.88 . ? C211 C216 1.384(3) . ? C211 C212 1.388(3) . ? C212 C213 1.383(3) . ? C212 H212 0.95 . ? C213 C214 1.381(3) . ? C213 H213 0.95 . ? C214 C215 1.388(3) . ? C214 H214 0.95 . ? C215 C216 1.382(3) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? N22 C221 1.425(2) . ? N22 H22 0.88 . ? C221 C222 1.385(3) . ? C221 C226 1.388(2) . ? C222 C223 1.388(3) . ? C222 H222 0.95 . ? C223 C224 1.386(3) . ? C223 H223 0.95 . ? C224 C225 1.373(3) . ? C224 H224 0.95 . ? C225 C226 1.390(3) . ? C225 H225 0.95 . ? C226 H226 0.95 . ? O1 H1A 0.80(2) . ? O1 H1B 0.81(3) . ? 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 108.04(2) . . ? S1 Cu1 Cl1 127.27(2) . . ? S2 Cu1 Cl1 124.68(2) . . ? C1 S1 Cu1 111.19(7) . . ? N12 C1 N11 118.76(16) . . ? N12 C1 S1 120.80(14) . . ? N11 C1 S1 120.44(15) . . ? C1 N11 C111 123.30(15) . . ? C1 N11 H11 118.3 . . ? C111 N11 H11 118.3 . . ? C116 C111 C112 120.61(19) . . ? C116 C111 N11 120.11(17) . . ? C112 C111 N11 119.28(18) . . ? C113 C112 C111 119.3(2) . . ? C113 C112 H112 120.4 . . ? C111 C112 H112 120.4 . . ? C114 C113 C112 120.46(19) . . ? C114 C113 H113 119.8 . . ? C112 C113 H113 119.8 . . ? C113 C114 C115 119.7(2) . . ? C113 C114 H114 120.2 . . ? C115 C114 H114 120.2 . . ? C116 C115 C114 120.2(2) . . ? C116 C115 H115 119.9 . . ? C114 C115 H115 119.9 . . ? C111 C116 C115 119.68(19) . . ? C111 C116 H116 120.2 . . ? C115 C116 H116 120.2 . . ? C1 N12 C121 124.36(16) . . ? C1 N12 H12 117.8 . . ? C121 N12 H12 117.8 . . ? C126 C121 C122 120.96(18) . . ? C126 C121 N12 120.14(18) . . ? C122 C121 N12 118.89(18) . . ? C121 C122 C123 119.3(2) . . ? C121 C122 H122 120.4 . . ? C123 C122 H122 120.4 . . ? C124 C123 C122 120.3(2) . . ? C124 C123 H123 119.9 . . ? C122 C123 H123 119.9 . . ? C123 C124 C125 120.08(19) . . ? C123 C124 H124 120 . . ? C125 C124 H124 120 . . ? C124 C125 C126 120.2(2) . . ? C124 C125 H125 119.9 . . ? C126 C125 H125 119.9 . . ? C121 C126 C125 119.2(2) . . ? C121 C126 H126 120.4 . . ? C125 C126 H126 120.4 . . ? C2 S2 Cu1 108.99(7) . . ? N22 C2 N21 118.67(18) . . ? N22 C2 S2 119.73(14) . . ? N21 C2 S2 121.54(16) . . ? C2 N21 C211 125.34(16) . . ? C2 N21 H21 117.3 . . ? C211 N21 H21 117.3 . . ? C216 C211 C212 120.00(19) . . ? C216 C211 N21 121.30(17) . . ? C212 C211 N21 118.64(17) . . ? C213 C212 C211 119.81(18) . . ? C213 C212 H212 120.1 . . ? C211 C212 H212 120.1 . . ? C214 C213 C212 120.28(19) . . ? C214 C213 H213 119.9 . . ? C212 C213 H213 119.9 . . ? C213 C214 C215 119.8(2) . . ? C213 C214 H214 120.1 . . ? C215 C214 H214 120.1 . . ? C216 C215 C214 120.15(19) . . ? C216 C215 H215 119.9 . . ? C214 C215 H215 119.9 . . ? C215 C216 C211 119.89(19) . . ? C215 C216 H216 120.1 . . ? C211 C216 H216 120.1 . . ? C2 N22 C221 129.52(16) . . ? C2 N22 H22 115.2 . . ? C221 N22 H22 115.2 . . ? C222 C221 C226 120.30(18) . . ? C222 C221 N22 117.67(16) . . ? C226 C221 N22 121.97(17) . . ? C221 C222 C223 119.88(18) . . ? C221 C222 H222 120.1 . . ? C223 C222 H222 120.1 . . ? C224 C223 C222 119.7(2) . . ? C224 C223 H223 120.2 . . ? C222 C223 H223 120.2 . . ? C225 C224 C223 120.4(2) . . ? C225 C224 H224 119.8 . . ? C223 C224 H224 119.8 . . ? C224 C225 C226 120.34(18) . . ? C224 C225 H225 119.8 . . ? C226 C225 H225 119.8 . . ? C221 C226 C225 119.36(18) . . ? C221 C226 H226 120.3 . . ? C225 C226 H226 120.3 . . ? H1A O1 H1B 106(2) . . ? #===END data_gb0715 _database_code_depnum_ccdc_archive 'CCDC 660460' _audit_creation_date 2007-11-14T07:52:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C26 H26 Br Cu N4 O S2' _chemical_formula_moiety 'C26 H24 Br Cu N4 S2, H2 O' _chemical_formula_weight 618.08 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4378(5) _cell_length_b 12.1456(6) _cell_length_c 12.6684(4) _cell_angle_alpha 90.047(3) _cell_angle_beta 73.966(3) _cell_angle_gamma 69.386(4) _cell_volume 1298.51(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10681 _cell_measurement_theta_min 3.3555 _cell_measurement_theta_max 37.5235 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.055 _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.62371 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0622971087 _diffrn_orient_matrix_ub_12 0.0559677401 _diffrn_orient_matrix_ub_13 0.0094996982 _diffrn_orient_matrix_ub_21 0.0552954822 _diffrn_orient_matrix_ub_22 0.0282314241 _diffrn_orient_matrix_ub_23 -0.0043898359 _diffrn_orient_matrix_ub_31 0.0107442887 _diffrn_orient_matrix_ub_32 0.0001379742 _diffrn_orient_matrix_ub_33 -0.0575544179 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0831 _diffrn_reflns_number 27220 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 37.63 _diffrn_reflns_theta_full 36.5 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.938 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 12945 _reflns_number_gt 8308 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0453P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 12945 _refine_ls_number_parameters 324 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.008 _refine_diff_density_max 0.967 _refine_diff_density_min -0.85 _refine_diff_density_rms 0.13 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.445832(9) 0.604967(7) 0.268191(6) 0.01384(2) Uani 1 1 d . . . Br1 Br 0.334507(7) 0.812611(6) 0.307922(5) 0.01611(2) Uani 1 1 d . . . S1 S 0.629153(18) 0.506188(14) 0.114691(12) 0.01381(4) Uani 1 1 d . . . C1 C 0.64633(7) 0.59530(5) 0.01103(5) 0.01128(13) Uani 1 1 d . . . N11 N 0.75998(6) 0.55270(5) -0.08593(4) 0.01414(13) Uani 1 1 d . . . H11 H 0.7652 0.6006 -0.1378 0.017 Uiso 1 1 calc R . . C111 C 0.87281(7) 0.43411(6) -0.10957(5) 0.01405(15) Uani 1 1 d . . . C112 C 1.03266(7) 0.41543(6) -0.13193(5) 0.01549(15) Uani 1 1 d . . . H112 H 1.0659 0.4807 -0.1321 0.019 Uiso 1 1 calc R . . C113 C 1.14436(8) 0.29968(7) -0.15426(5) 0.01984(17) Uani 1 1 d . . . H113 H 1.254 0.2863 -0.1706 0.024 Uiso 1 1 calc R . . C114 C 1.09508(9) 0.20444(7) -0.15258(6) 0.02241(19) Uani 1 1 d . . . H114 H 1.1704 0.1257 -0.1657 0.027 Uiso 1 1 calc R . . C115 C 0.93438(9) 0.22508(6) -0.13158(5) 0.02037(17) Uani 1 1 d . . . H115 H 0.9005 0.1601 -0.1313 0.024 Uiso 1 1 calc R . . C116 C 0.82402(8) 0.33910(6) -0.11126(5) 0.01624(15) Uani 1 1 d . . . H116 H 0.7149 0.3525 -0.0985 0.019 Uiso 1 1 calc R . . N12 N 0.54821(6) 0.70842(5) 0.02489(4) 0.01333(13) Uani 1 1 d . . . H12 H 0.4837 0.7381 0.0915 0.016 Uiso 1 1 calc R . . C121 C 0.54096(7) 0.78491(5) -0.06173(5) 0.01385(14) Uani 1 1 d . . . C122 C 0.45048(8) 0.78086(6) -0.12993(6) 0.01975(16) Uani 1 1 d . . . H122 H 0.395 0.728 -0.1197 0.024 Uiso 1 1 calc R . . C123 C 0.44146(9) 0.85523(7) -0.21415(6) 0.02410(18) Uani 1 1 d . . . H123 H 0.3791 0.8537 -0.2611 0.029 Uiso 1 1 calc R . . C124 C 0.52435(9) 0.93142(6) -0.22858(6) 0.02197(18) Uani 1 1 d . . . H124 H 0.5183 0.9822 -0.2855 0.026 Uiso 1 1 calc R . . C125 C 0.61584(9) 0.93383(6) -0.16035(6) 0.02437(18) Uani 1 1 d . . . H125 H 0.6726 0.9858 -0.171 0.029 Uiso 1 1 calc R . . C126 C 0.62456(8) 0.86027(6) -0.07636(6) 0.01862(16) Uani 1 1 d . . . H126 H 0.6872 0.8617 -0.0295 0.022 Uiso 1 1 calc R . . S2 S 0.387676(18) 0.475109(14) 0.379267(12) 0.01395(4) Uani 1 1 d . . . C2 C 0.26080(7) 0.54768(5) 0.50575(5) 0.01173(13) Uani 1 1 d . . . N21 N 0.18004(6) 0.49492(4) 0.57825(4) 0.01235(12) Uani 1 1 d . . . H21 H 0.1073 0.5394 0.6371 0.015 Uiso 1 1 calc R . . C211 C 0.20201(7) 0.37229(5) 0.56810(5) 0.01185(14) Uani 1 1 d . . . C212 C 0.06838(7) 0.34231(6) 0.58800(5) 0.01581(15) Uani 1 1 d . . . H212 H -0.0343 0.4025 0.6071 0.019 Uiso 1 1 calc R . . C213 C 0.08595(8) 0.22382(6) 0.57972(5) 0.01812(16) Uani 1 1 d . . . H213 H -0.005 0.203 0.5927 0.022 Uiso 1 1 calc R . . C214 C 0.23621(9) 0.13549(6) 0.55256(6) 0.02164(18) Uani 1 1 d . . . H214 H 0.2482 0.0546 0.5451 0.026 Uiso 1 1 calc R . . C215 C 0.36857(8) 0.16642(6) 0.53638(6) 0.02238(19) Uani 1 1 d . . . H215 H 0.471 0.1062 0.5193 0.027 Uiso 1 1 calc R . . C216 C 0.35256(8) 0.28447(6) 0.54501(5) 0.01637(15) Uani 1 1 d . . . H216 H 0.4431 0.3052 0.5353 0.02 Uiso 1 1 calc R . . N22 N 0.23655(6) 0.66132(5) 0.52993(4) 0.01306(13) Uani 1 1 d . . . H22 H 0.2744 0.696 0.4739 0.016 Uiso 1 1 calc R . . C221 C 0.15908(7) 0.73482(5) 0.63220(5) 0.01332(14) Uani 1 1 d . . . C222 C 0.09105(8) 0.85519(6) 0.62839(6) 0.01859(17) Uani 1 1 d . . . H222 H 0.0919 0.8856 0.5592 0.022 Uiso 1 1 calc R . . C223 C 0.02112(9) 0.93226(7) 0.72578(6) 0.02295(19) Uani 1 1 d . . . H223 H -0.0244 1.0151 0.7232 0.028 Uiso 1 1 calc R . . C224 C 0.01853(8) 0.88669(6) 0.82691(6) 0.02062(17) Uani 1 1 d . . . H224 H -0.0308 0.9385 0.8936 0.025 Uiso 1 1 calc R . . C225 C 0.08788(8) 0.76565(6) 0.83039(5) 0.01699(16) Uani 1 1 d . . . H225 H 0.0857 0.7352 0.8996 0.02 Uiso 1 1 calc R . . C226 C 0.16031(7) 0.68876(6) 0.73372(5) 0.01493(15) Uani 1 1 d . . . H226 H 0.21 0.6062 0.7362 0.018 Uiso 1 1 calc R . . O1 O 0.15604(6) 0.35548(4) 0.29842(4) 0.01791(12) Uani 1 1 d D . . H1A H 0.2080(9) 0.3825(7) 0.3225(7) 0.020(2) Uiso 1 1 d D . . H1B H 0.1650(13) 0.2922(9) 0.2964(9) 0.056(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01479(3) 0.01461(3) 0.01095(3) 0.00243(2) -0.00133(2) -0.00588(2) Br1 0.01891(2) 0.01346(2) 0.01553(2) 0.00359(2) -0.00355(2) -0.00660(2) S1 0.01574(6) 0.01234(5) 0.01066(5) 0.00312(5) -0.00110(5) -0.00409(4) C1 0.01134(19) 0.0152(2) 0.00944(19) 0.00188(17) -0.00330(16) -0.00720(16) N11 0.01289(19) 0.0146(2) 0.0131(2) 0.00404(17) -0.00158(16) -0.00459(15) C111 0.0148(2) 0.0164(2) 0.0090(2) 0.00048(19) -0.00129(18) -0.00512(18) C112 0.0137(2) 0.0172(2) 0.0144(2) 0.0008(2) -0.00310(18) -0.00511(18) C113 0.0143(2) 0.0253(3) 0.0159(2) -0.0022(2) -0.00562(19) -0.0018(2) C114 0.0219(3) 0.0191(3) 0.0187(3) -0.0014(2) -0.0066(2) 0.0019(2) C115 0.0273(3) 0.0148(3) 0.0156(2) -0.0018(2) -0.0039(2) -0.0055(2) C116 0.0171(2) 0.0151(2) 0.0143(2) -0.0006(2) -0.00284(19) -0.00472(19) N12 0.0170(2) 0.01196(19) 0.00936(18) 0.00324(16) -0.00206(15) -0.00467(15) C121 0.0145(2) 0.0137(2) 0.0119(2) 0.00324(19) -0.00226(18) -0.00461(17) C122 0.0220(2) 0.0189(2) 0.0241(3) 0.0090(2) -0.0111(2) -0.01099(19) C123 0.0278(3) 0.0281(3) 0.0231(3) 0.0125(2) -0.0134(2) -0.0135(2) C124 0.0256(3) 0.0204(3) 0.0184(3) 0.0089(2) -0.0062(2) -0.0069(2) C125 0.0307(3) 0.0197(3) 0.0267(3) 0.0091(2) -0.0070(2) -0.0151(2) C126 0.0235(2) 0.0166(2) 0.0200(3) 0.0053(2) -0.0083(2) -0.01099(18) S2 0.01610(6) 0.01228(6) 0.01025(5) 0.00019(5) 0.00084(5) -0.00501(4) C2 0.0127(2) 0.0118(2) 0.0105(2) 0.00198(18) -0.00378(17) -0.00399(16) N21 0.0169(2) 0.00971(18) 0.00837(18) -0.00012(15) -0.00076(16) -0.00465(15) C211 0.0154(2) 0.0106(2) 0.0090(2) 0.00150(17) -0.00352(17) -0.00424(16) C212 0.0163(2) 0.0183(2) 0.0139(2) 0.0022(2) -0.00308(19) -0.00869(18) C213 0.0188(2) 0.0220(3) 0.0184(3) 0.0038(2) -0.00670(19) -0.01233(18) C214 0.0259(3) 0.0133(2) 0.0265(3) 0.0028(2) -0.0056(2) -0.00972(19) C215 0.0177(3) 0.0129(2) 0.0314(3) 0.0047(2) -0.0027(2) -0.0031(2) C216 0.0160(2) 0.0143(2) 0.0189(3) 0.0017(2) -0.0029(2) -0.00746(17) N22 0.0166(2) 0.01178(19) 0.00918(19) 0.00105(16) -0.00139(16) -0.00515(15) C221 0.0149(2) 0.0124(2) 0.0122(2) -0.00011(18) -0.00241(18) -0.00575(17) C222 0.0245(3) 0.0106(2) 0.0196(3) 0.0035(2) -0.0077(2) -0.0042(2) C223 0.0279(3) 0.0147(3) 0.0215(3) -0.0021(2) -0.0064(2) -0.0029(2) C224 0.0222(3) 0.0180(3) 0.0190(3) -0.0035(2) -0.0073(2) -0.0033(2) C225 0.0203(2) 0.0165(2) 0.0129(2) -0.0001(2) -0.00439(19) -0.00565(19) C226 0.0182(2) 0.0144(2) 0.0128(2) 0.00149(19) -0.00551(18) -0.00600(18) O1 0.01890(19) 0.0194(2) 0.01376(17) 0.00017(16) -0.00310(15) -0.00637(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.21139(19) . ? Cu1 S2 2.2261(2) . ? Cu1 Br1 2.35745(16) . ? S1 C1 1.7120(6) . ? C1 N12 1.3378(7) . ? C1 N11 1.3443(7) . ? N11 C111 1.4288(8) . ? N11 H11 0.88 . ? C111 C116 1.3869(11) . ? C111 C112 1.3895(10) . ? C112 C113 1.3996(9) . ? C112 H112 0.95 . ? C113 C114 1.3885(13) . ? C113 H113 0.95 . ? C114 C115 1.3939(11) . ? C114 H114 0.95 . ? C115 C116 1.3800(9) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? N12 C121 1.4388(8) . ? N12 H12 0.88 . ? C121 C122 1.3839(11) . ? C121 C126 1.3867(11) . ? C122 C123 1.3996(10) . ? C122 H122 0.95 . ? C123 C124 1.3903(13) . ? C123 H123 0.95 . ? C124 C125 1.3869(13) . ? C124 H124 0.95 . ? C125 C126 1.3911(10) . ? C125 H125 0.95 . ? C126 H126 0.95 . ? S2 C2 1.7242(5) . ? C2 N22 1.3377(9) . ? C2 N21 1.3392(8) . ? N21 C211 1.4302(8) . ? N21 H21 0.88 . ? C211 C212 1.3908(10) . ? C211 C216 1.3946(8) . ? C212 C213 1.3899(10) . ? C212 H212 0.95 . ? C213 C214 1.3925(9) . ? C213 H213 0.95 . ? C214 C215 1.3902(12) . ? C214 H214 0.95 . ? C215 C216 1.3888(10) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? N22 C221 1.4231(7) . ? N22 H22 0.88 . ? C221 C222 1.3813(9) . ? C221 C226 1.4043(9) . ? C222 C223 1.3955(9) . ? C222 H222 0.95 . ? C223 C224 1.3934(11) . ? C223 H223 0.95 . ? C224 C225 1.3893(10) . ? C224 H224 0.95 . ? C225 C226 1.3876(8) . ? C225 H225 0.95 . ? C226 H226 0.95 . ? O1 H1A 0.799(10) . ? O1 H1B 0.743(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Cu1 S2 108.433(7) . . ? S1 Cu1 Br1 125.575(7) . . ? S2 Cu1 Br1 125.986(6) . . ? C1 S1 Cu1 111.905(19) . . ? N12 C1 N11 118.74(5) . . ? N12 C1 S1 120.92(4) . . ? N11 C1 S1 120.34(4) . . ? C1 N11 C111 123.71(5) . . ? C1 N11 H11 118.1 . . ? C111 N11 H11 118.1 . . ? C116 C111 C112 120.44(6) . . ? C116 C111 N11 120.66(6) . . ? C112 C111 N11 118.90(7) . . ? C111 C112 C113 119.50(7) . . ? C111 C112 H112 120.3 . . ? C113 C112 H112 120.2 . . ? C114 C113 C112 120.05(7) . . ? C114 C113 H113 120 . . ? C112 C113 H113 120 . . ? C113 C114 C115 119.56(6) . . ? C113 C114 H114 120.2 . . ? C115 C114 H114 120.2 . . ? C116 C115 C114 120.60(8) . . ? C116 C115 H115 119.7 . . ? C114 C115 H115 119.7 . . ? C115 C116 C111 119.81(7) . . ? C115 C116 H116 120.1 . . ? C111 C116 H116 120.1 . . ? C1 N12 C121 124.47(5) . . ? C1 N12 H12 117.8 . . ? C121 N12 H12 117.8 . . ? C122 C121 C126 121.10(6) . . ? C122 C121 N12 118.78(7) . . ? C126 C121 N12 120.12(7) . . ? C121 C122 C123 119.46(8) . . ? C121 C122 H122 120.3 . . ? C123 C122 H122 120.3 . . ? C124 C123 C122 119.57(8) . . ? C124 C123 H123 120.2 . . ? C122 C123 H123 120.2 . . ? C125 C124 C123 120.42(7) . . ? C125 C124 H124 119.8 . . ? C123 C124 H124 119.8 . . ? C124 C125 C126 120.11(8) . . ? C124 C125 H125 119.9 . . ? C126 C125 H125 119.9 . . ? C121 C126 C125 119.33(7) . . ? C121 C126 H126 120.3 . . ? C125 C126 H126 120.3 . . ? C2 S2 Cu1 109.94(2) . . ? N22 C2 N21 119.08(5) . . ? N22 C2 S2 119.16(5) . . ? N21 C2 S2 121.67(5) . . ? C2 N21 C211 125.49(4) . . ? C2 N21 H21 117.3 . . ? C211 N21 H21 117.3 . . ? C212 C211 C216 120.52(6) . . ? C212 C211 N21 118.29(5) . . ? C216 C211 N21 121.10(6) . . ? C213 C212 C211 119.59(5) . . ? C213 C212 H212 120.2 . . ? C211 C212 H212 120.2 . . ? C212 C213 C214 120.30(7) . . ? C212 C213 H213 119.8 . . ? C214 C213 H213 119.8 . . ? C215 C214 C213 119.58(7) . . ? C215 C214 H214 120.2 . . ? C213 C214 H214 120.2 . . ? C216 C215 C214 120.66(6) . . ? C216 C215 H215 119.7 . . ? C214 C215 H215 119.7 . . ? C215 C216 C211 119.25(7) . . ? C215 C216 H216 120.4 . . ? C211 C216 H216 120.4 . . ? C2 N22 C221 130.00(5) . . ? C2 N22 H22 115 . . ? C221 N22 H22 115 . . ? C222 C221 C226 120.51(6) . . ? C222 C221 N22 117.65(6) . . ? C226 C221 N22 121.70(5) . . ? C221 C222 C223 120.21(6) . . ? C221 C222 H222 119.9 . . ? C223 C222 H222 119.9 . . ? C224 C223 C222 119.49(7) . . ? C224 C223 H223 120.3 . . ? C222 C223 H223 120.3 . . ? C225 C224 C223 120.14(6) . . ? C225 C224 H224 119.9 . . ? C223 C224 H224 119.9 . . ? C226 C225 C224 120.65(6) . . ? C226 C225 H225 119.7 . . ? C224 C225 H225 119.7 . . ? C225 C226 C221 118.97(6) . . ? C225 C226 H226 120.5 . . ? C221 C226 H226 120.5 . . ? H1A O1 H1B 124.7(11) . . ? #===END data_gb0711 _database_code_depnum_ccdc_archive 'CCDC 660461' _audit_creation_date 2007-11-14T09:24:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C26 H26 Cu I N4 O S2' _chemical_formula_moiety 'C26 H24 Cu I N4 S2, H2 O' _chemical_formula_weight 665.07 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P_-1 _symmetry_space_group_name_Hall -p_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5132(3) _cell_length_b 12.4449(3) _cell_length_c 12.7948(2) _cell_angle_alpha 91.807(2) _cell_angle_beta 73.165(2) _cell_angle_gamma 69.216(3) _cell_volume 1340.16(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 17738 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 37.4691 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.64082 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0332647555 _diffrn_orient_matrix_ub_12 0.0615772463 _diffrn_orient_matrix_ub_13 0.0057142012 _diffrn_orient_matrix_ub_21 0.0694044536 _diffrn_orient_matrix_ub_22 0.0024037532 _diffrn_orient_matrix_ub_23 0.0083194635 _diffrn_orient_matrix_ub_31 0.0343101937 _diffrn_orient_matrix_ub_32 -0.0029705807 _diffrn_orient_matrix_ub_33 -0.0576929682 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.074 _diffrn_reflns_number 47834 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 37.59 _diffrn_reflns_theta_full 36.75 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.96 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 13635 _reflns_number_gt 8846 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0477P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 13635 _refine_ls_number_parameters 324 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0903 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.61 _refine_diff_density_min -1.357 _refine_diff_density_rms 0.179 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.44177(3) 0.61062(2) 0.272642(19) 0.01620(5) Uani 1 1 d . . . I1 I 0.329167(15) 0.829005(11) 0.321602(10) 0.01837(4) Uani 1 1 d . . . S1 S 0.62516(6) 0.50971(4) 0.11431(4) 0.01646(9) Uani 1 1 d . . . C1 C 0.6427(2) 0.59441(16) 0.01168(15) 0.0148(3) Uani 1 1 d . . . N11 N 0.75685(19) 0.55217(14) -0.08537(13) 0.0166(3) Uani 1 1 d . . . H11 H 0.7603 0.5981 -0.1361 0.02 Uiso 1 1 calc R . . C111 C 0.8743(2) 0.43643(17) -0.11201(14) 0.0160(3) Uani 1 1 d . . . C112 C 1.0339(2) 0.41955(18) -0.13474(16) 0.0191(4) Uani 1 1 d . . . H112 H 1.0643 0.4842 -0.1321 0.023 Uiso 1 1 calc R . . C113 C 1.1477(2) 0.3071(2) -0.16127(17) 0.0227(4) Uani 1 1 d . . . H113 H 1.2565 0.2955 -0.1777 0.027 Uiso 1 1 calc R . . C114 C 1.1059(3) 0.21219(19) -0.16426(18) 0.0257(4) Uani 1 1 d . . . H114 H 1.1846 0.1356 -0.1812 0.031 Uiso 1 1 calc R . . C115 C 0.9460(3) 0.23018(19) -0.14194(18) 0.0244(4) Uani 1 1 d . . . H115 H 0.9158 0.1653 -0.1435 0.029 Uiso 1 1 calc R . . C116 C 0.8310(3) 0.34155(18) -0.11759(17) 0.0213(4) Uani 1 1 d . . . H116 H 0.7228 0.353 -0.1047 0.026 Uiso 1 1 calc R . . N12 N 0.5400(2) 0.70534(14) 0.02811(13) 0.0165(3) Uani 1 1 d . . . H12 H 0.4729 0.735 0.0951 0.02 Uiso 1 1 calc R . . C121 C 0.5324(2) 0.77871(16) -0.05647(15) 0.0161(3) Uani 1 1 d . . . C122 C 0.4406(3) 0.77454(19) -0.12184(18) 0.0241(4) Uani 1 1 d . . . H122 H 0.385 0.7236 -0.1112 0.029 Uiso 1 1 calc R . . C123 C 0.4308(3) 0.8459(2) -0.20350(19) 0.0290(5) Uani 1 1 d . . . H123 H 0.3692 0.843 -0.2494 0.035 Uiso 1 1 calc R . . C124 C 0.5102(3) 0.92061(19) -0.21785(18) 0.0253(4) Uani 1 1 d . . . H124 H 0.5018 0.97 -0.2728 0.03 Uiso 1 1 calc R . . C125 C 0.6029(3) 0.92397(19) -0.15178(18) 0.0258(4) Uani 1 1 d . . . H125 H 0.6586 0.9749 -0.1623 0.031 Uiso 1 1 calc R . . C126 C 0.6136(3) 0.85256(19) -0.07057(17) 0.0219(4) Uani 1 1 d . . . H126 H 0.6763 0.8546 -0.0252 0.026 Uiso 1 1 calc R . . S2 S 0.38636(6) 0.48068(4) 0.37698(4) 0.01679(9) Uani 1 1 d . . . C2 C 0.2600(2) 0.54763(16) 0.50734(14) 0.0140(3) Uani 1 1 d . . . N21 N 0.1807(2) 0.49340(14) 0.57647(13) 0.0163(3) Uani 1 1 d . . . H21 H 0.108 0.5359 0.6378 0.02 Uiso 1 1 calc R . . C211 C 0.2033(2) 0.37387(16) 0.55970(14) 0.0145(3) Uani 1 1 d . . . C212 C 0.0691(2) 0.34612(17) 0.58190(16) 0.0180(3) Uani 1 1 d . . . H212 H -0.034 0.4059 0.6062 0.022 Uiso 1 1 calc R . . C213 C 0.0875(3) 0.23005(19) 0.56817(17) 0.0220(4) Uani 1 1 d . . . H213 H -0.0036 0.2106 0.5835 0.026 Uiso 1 1 calc R . . C214 C 0.2375(3) 0.14253(18) 0.53235(18) 0.0245(4) Uani 1 1 d . . . H214 H 0.2493 0.0636 0.5211 0.029 Uiso 1 1 calc R . . C215 C 0.3702(3) 0.17085(19) 0.51302(18) 0.0245(4) Uani 1 1 d . . . H215 H 0.4731 0.1108 0.4896 0.029 Uiso 1 1 calc R . . C216 C 0.3545(2) 0.28635(17) 0.52749(17) 0.0191(4) Uani 1 1 d . . . H216 H 0.4457 0.3053 0.5156 0.023 Uiso 1 1 calc R . . N22 N 0.23302(19) 0.65850(14) 0.53917(13) 0.0161(3) Uani 1 1 d . . . H22 H 0.2704 0.6944 0.4864 0.019 Uiso 1 1 calc R . . C221 C 0.1529(2) 0.72734(16) 0.64559(15) 0.0159(3) Uani 1 1 d . . . C222 C 0.0747(3) 0.84591(18) 0.65020(17) 0.0228(4) Uani 1 1 d . . . H222 H 0.0698 0.8778 0.5843 0.027 Uiso 1 1 calc R . . C223 C 0.0038(3) 0.9175(2) 0.7512(2) 0.0308(5) Uani 1 1 d . . . H223 H -0.0462 0.9991 0.7539 0.037 Uiso 1 1 calc R . . C224 C 0.0049(3) 0.8714(2) 0.84926(19) 0.0280(5) Uani 1 1 d . . . H224 H -0.0462 0.9208 0.9185 0.034 Uiso 1 1 calc R . . C225 C 0.0815(2) 0.75267(19) 0.84432(16) 0.0217(4) Uani 1 1 d . . . H225 H 0.0817 0.7204 0.9106 0.026 Uiso 1 1 calc R . . C226 C 0.1583(2) 0.68034(17) 0.74267(15) 0.0174(3) Uani 1 1 d . . . H226 H 0.2141 0.5994 0.7395 0.021 Uiso 1 1 calc R . . O1 O 0.15951(18) 0.35942(13) 0.29458(12) 0.0209(3) Uani 1 1 d D . . H1A H 0.198(4) 0.385(3) 0.333(3) 0.062(12) Uiso 1 1 d D . . H1B H 0.183(3) 0.2896(15) 0.281(2) 0.033(8) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01706(11) 0.01684(11) 0.01385(10) 0.00359(8) -0.00385(8) -0.00629(9) I1 0.02138(6) 0.01584(6) 0.01828(6) 0.00468(4) -0.00641(4) -0.00733(5) S1 0.0173(2) 0.0154(2) 0.01428(19) 0.00447(15) -0.00328(16) -0.00475(16) C1 0.0148(8) 0.0162(8) 0.0147(7) 0.0033(6) -0.0056(6) -0.0064(6) N11 0.0178(7) 0.0177(7) 0.0136(7) 0.0041(6) -0.0034(6) -0.0069(6) C111 0.0155(8) 0.0179(8) 0.0122(7) 0.0013(6) -0.0041(6) -0.0041(7) C112 0.0191(9) 0.0237(9) 0.0161(8) 0.0021(7) -0.0061(7) -0.0098(7) C113 0.0150(8) 0.0313(11) 0.0178(8) -0.0021(8) -0.0061(7) -0.0041(8) C114 0.0286(11) 0.0193(9) 0.0211(9) -0.0058(7) -0.0108(8) 0.0017(8) C115 0.0291(11) 0.0197(9) 0.0250(10) -0.0010(8) -0.0103(8) -0.0091(8) C116 0.0224(9) 0.0211(9) 0.0198(9) 0.0006(7) -0.0074(7) -0.0071(8) N12 0.0200(8) 0.0140(7) 0.0118(6) 0.0017(5) -0.0033(6) -0.0038(6) C121 0.0185(8) 0.0141(8) 0.0128(7) 0.0029(6) -0.0035(6) -0.0039(7) C122 0.0241(10) 0.0261(10) 0.0286(10) 0.0127(8) -0.0125(8) -0.0131(8) C123 0.0340(12) 0.0333(12) 0.0290(11) 0.0171(9) -0.0197(9) -0.0150(10) C124 0.0301(11) 0.0215(10) 0.0215(9) 0.0097(8) -0.0068(8) -0.0074(8) C125 0.0331(12) 0.0225(10) 0.0259(10) 0.0067(8) -0.0087(9) -0.0156(9) C126 0.0288(10) 0.0238(10) 0.0197(9) 0.0051(7) -0.0112(8) -0.0146(8) S2 0.0189(2) 0.0148(2) 0.01361(18) 0.00198(15) -0.00185(16) -0.00559(17) C2 0.0144(8) 0.0148(8) 0.0126(7) 0.0018(6) -0.0049(6) -0.0050(6) N21 0.0191(7) 0.0144(7) 0.0138(7) 0.0011(5) -0.0033(6) -0.0062(6) C211 0.0185(8) 0.0156(8) 0.0114(7) 0.0022(6) -0.0058(6) -0.0080(7) C212 0.0175(8) 0.0203(9) 0.0172(8) 0.0050(7) -0.0057(7) -0.0079(7) C213 0.0244(10) 0.0259(10) 0.0223(9) 0.0061(8) -0.0086(8) -0.0158(8) C214 0.0335(11) 0.0164(9) 0.0263(10) 0.0042(7) -0.0108(9) -0.0114(8) C215 0.0235(10) 0.0172(9) 0.0272(10) 0.0038(8) -0.0050(8) -0.0039(8) C216 0.0181(9) 0.0166(8) 0.0238(9) 0.0067(7) -0.0085(7) -0.0064(7) N22 0.0194(7) 0.0143(7) 0.0139(7) 0.0030(5) -0.0041(6) -0.0066(6) C221 0.0142(8) 0.0159(8) 0.0174(8) 0.0014(6) -0.0052(6) -0.0053(7) C222 0.0321(11) 0.0166(9) 0.0221(9) 0.0019(7) -0.0149(8) -0.0071(8) C223 0.0363(13) 0.0178(9) 0.0326(11) -0.0042(8) -0.0182(10) 0.0014(9) C224 0.0269(11) 0.0256(10) 0.0234(10) -0.0062(8) -0.0112(8) 0.0007(9) C225 0.0226(9) 0.0266(10) 0.0141(8) -0.0025(7) -0.0078(7) -0.0062(8) C226 0.0197(9) 0.0185(8) 0.0147(8) 0.0005(6) -0.0075(7) -0.0065(7) O1 0.0236(7) 0.0209(7) 0.0174(6) 0.0009(5) -0.0057(6) -0.0085(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.2276(5) . ? Cu1 S2 2.2380(5) . ? Cu1 I1 2.5227(3) . ? S1 C1 1.7170(18) . ? C1 N11 1.331(2) . ? C1 N12 1.345(2) . ? N11 C111 1.430(2) . ? N11 H11 0.88 . ? C111 C116 1.388(3) . ? C111 C112 1.396(3) . ? C112 C113 1.388(3) . ? C112 H112 0.95 . ? C113 C114 1.377(3) . ? C113 H113 0.95 . ? C114 C115 1.396(3) . ? C114 H114 0.95 . ? C115 C116 1.384(3) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? N12 C121 1.439(2) . ? N12 H12 0.88 . ? C121 C126 1.382(3) . ? C121 C122 1.384(3) . ? C122 C123 1.395(3) . ? C122 H122 0.95 . ? C123 C124 1.377(3) . ? C123 H123 0.95 . ? C124 C125 1.397(3) . ? C124 H124 0.95 . ? C125 C126 1.391(3) . ? C125 H125 0.95 . ? C126 H126 0.95 . ? S2 C2 1.7209(18) . ? C2 N22 1.337(2) . ? C2 N21 1.349(2) . ? N21 C211 1.425(2) . ? N21 H21 0.88 . ? C211 C212 1.393(3) . ? C211 C216 1.393(3) . ? C212 C213 1.391(3) . ? C212 H212 0.95 . ? C213 C214 1.385(3) . ? C213 H213 0.95 . ? C214 C215 1.386(3) . ? C214 H214 0.95 . ? C215 C216 1.392(3) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? N22 C221 1.425(2) . ? N22 H22 0.88 . ? C221 C222 1.387(3) . ? C221 C226 1.396(3) . ? C222 C223 1.384(3) . ? C222 H222 0.95 . ? C223 C224 1.398(3) . ? C223 H223 0.95 . ? C224 C225 1.386(3) . ? C224 H224 0.95 . ? C225 C226 1.394(3) . ? C225 H225 0.95 . ? C226 H226 0.95 . ? O1 H1A 0.81(2) . ? O1 H1B 0.816(16) . ? 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 106.621(19) . . ? S1 Cu1 I1 125.305(16) . . ? S2 Cu1 I1 128.052(15) . . ? C1 S1 Cu1 112.43(7) . . ? N11 C1 N12 118.66(16) . . ? N11 C1 S1 121.07(14) . . ? N12 C1 S1 120.27(14) . . ? C1 N11 C111 123.82(16) . . ? C1 N11 H11 118.1 . . ? C111 N11 H11 118.1 . . ? C116 C111 C112 120.07(18) . . ? C116 C111 N11 120.53(18) . . ? C112 C111 N11 119.39(18) . . ? C113 C112 C111 119.2(2) . . ? C113 C112 H112 120.4 . . ? C111 C112 H112 120.4 . . ? C114 C113 C112 121.3(2) . . ? C114 C113 H113 119.4 . . ? C112 C113 H113 119.4 . . ? C113 C114 C115 118.97(19) . . ? C113 C114 H114 120.5 . . ? C115 C114 H114 120.5 . . ? C116 C115 C114 120.7(2) . . ? C116 C115 H115 119.7 . . ? C114 C115 H115 119.7 . . ? C115 C116 C111 119.7(2) . . ? C115 C116 H116 120.1 . . ? C111 C116 H116 120.1 . . ? C1 N12 C121 124.43(15) . . ? C1 N12 H12 117.8 . . ? C121 N12 H12 117.8 . . ? C126 C121 C122 121.11(18) . . ? C126 C121 N12 120.31(18) . . ? C122 C121 N12 118.57(18) . . ? C121 C122 C123 119.3(2) . . ? C121 C122 H122 120.4 . . ? C123 C122 H122 120.4 . . ? C124 C123 C122 120.2(2) . . ? C124 C123 H123 119.9 . . ? C122 C123 H123 119.9 . . ? C123 C124 C125 120.13(19) . . ? C123 C124 H124 119.9 . . ? C125 C124 H124 119.9 . . ? C126 C125 C124 119.8(2) . . ? C126 C125 H125 120.1 . . ? C124 C125 H125 120.1 . . ? C121 C126 C125 119.4(2) . . ? C121 C126 H126 120.3 . . ? C125 C126 H126 120.3 . . ? C2 S2 Cu1 110.96(7) . . ? N22 C2 N21 118.83(16) . . ? N22 C2 S2 119.23(14) . . ? N21 C2 S2 121.84(14) . . ? C2 N21 C211 126.28(15) . . ? C2 N21 H21 116.9 . . ? C211 N21 H21 116.9 . . ? C212 C211 C216 120.47(18) . . ? C212 C211 N21 118.06(17) . . ? C216 C211 N21 121.39(17) . . ? C213 C212 C211 119.30(18) . . ? C213 C212 H212 120.4 . . ? C211 C212 H212 120.4 . . ? C214 C213 C212 120.7(2) . . ? C214 C213 H213 119.7 . . ? C212 C213 H213 119.7 . . ? C213 C214 C215 119.6(2) . . ? C213 C214 H214 120.2 . . ? C215 C214 H214 120.2 . . ? C214 C215 C216 120.7(2) . . ? C214 C215 H215 119.7 . . ? C216 C215 H215 119.7 . . ? C215 C216 C211 119.22(19) . . ? C215 C216 H216 120.4 . . ? C211 C216 H216 120.4 . . ? C2 N22 C221 129.78(16) . . ? C2 N22 H22 115.1 . . ? C221 N22 H22 115.1 . . ? C222 C221 C226 120.07(17) . . ? C222 C221 N22 117.56(17) . . ? C226 C221 N22 122.28(16) . . ? C223 C222 C221 119.77(19) . . ? C223 C222 H222 120.1 . . ? C221 C222 H222 120.1 . . ? C222 C223 C224 120.8(2) . . ? C222 C223 H223 119.6 . . ? C224 C223 H223 119.6 . . ? C225 C224 C223 119.2(2) . . ? C225 C224 H224 120.4 . . ? C223 C224 H224 120.4 . . ? C224 C225 C226 120.41(19) . . ? C224 C225 H225 119.8 . . ? C226 C225 H225 119.8 . . ? C225 C226 C221 119.71(18) . . ? C225 C226 H226 120.1 . . ? C221 C226 H226 120.1 . . ? H1A O1 H1B 121(3) . . ? #===END data_cusodp _database_code_depnum_ccdc_archive 'CCDC 660462' _audit_creation_date 2007-09-08T21:20:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C27.75 H26.25 Cu N4.25 O2.50 S2.75' _chemical_formula_moiety 'C26 H24 Cu N4 S2, .25(C7 H5 N S),.5(O4 S),0.5(H2 O)' _chemical_formula_weight 610.98 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-p 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 17.3670(10) _cell_length_b 24.495(2) _cell_length_c 13.2920(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5654.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.9 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2524 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.011 _diffrn_measurement_device_type ; Bruker SMART CCD diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS; Sheldrick, 1996 ; _exptl_absorpt_correction_T_min .753 _exptl_absorpt_correction_T_max .892 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents .0292 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_number 65458 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 29.12 _diffrn_reflns_theta_full 28.75 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.963 _reflns_number_total 7472 _reflns_number_gt 5929 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Siemens SMART (Siemens, 1995)' _computing_cell_refinement 'Siemens SAINT (Siemens, 1995)' _computing_data_reduction xtal _computing_structure_solution xtal _computing_molecular_graphics xtal _computing_publication_material 'xtal BONDLA CIFIO' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0539P)^2^+2.3889P] 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_number_reflns 7472 _refine_ls_number_parameters 448 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.035 _refine_ls_wR_factor_ref 0.099 _refine_ls_wR_factor_gt 0.093 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 _refine_diff_density_max 0.721 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.062 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 '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' 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 Cu Cu 0.732730(14) 0.510604(9) 0.701938(18) 0.03277(8) Uani 1 1 d . . . S1 S 0.63503(3) 0.559394(18) 0.65149(4) 0.03185(11) Uani 1 1 d . . . S2 S 0.82620(3) 0.451422(17) 0.70567(3) 0.03052(11) Uani 1 1 d . . . N1 N 0.63388(8) 0.64299(6) 0.52271(12) 0.0289(3) Uani 1 1 d . . . H1 H 0.6549 0.6737 0.5023 0.035 Uiso 1 1 calc R . . N2 N 0.74838(8) 0.62956(6) 0.59842(11) 0.0255(3) Uani 1 1 d . . . H2 H 0.7649 0.6537 0.5545 0.031 Uiso 1 1 calc R . . N3 N 0.73021(9) 0.39199(6) 0.82309(12) 0.0295(3) Uani 1 1 d . . . H3 H 0.7165 0.3596 0.8455 0.035 Uiso 1 1 calc R . . N4 N 0.82064(9) 0.34494(6) 0.73597(13) 0.0348(4) Uani 1 1 d . . . H4 H 0.8117 0.3171 0.7761 0.042 Uiso 1 1 calc R A 1 C1 C 0.67526(10) 0.61303(6) 0.58796(13) 0.0247(3) Uani 1 1 d . . . C11 C 0.55974(10) 0.63045(7) 0.48300(14) 0.0286(4) Uani 1 1 d . . . C12 C 0.50477(13) 0.67069(9) 0.4831(2) 0.0598(7) Uani 1 1 d . . . H12 H 0.5158 0.7053 0.512 0.072 Uiso 1 1 calc R . . C13 C 0.43268(14) 0.66066(12) 0.4409(2) 0.0646(8) Uani 1 1 d . . . H13 H 0.395 0.6888 0.4399 0.078 Uiso 1 1 calc R . . C14 C 0.41584(12) 0.61108(11) 0.40118(16) 0.0478(5) Uani 1 1 d . . . H14 H 0.3665 0.6043 0.373 0.057 Uiso 1 1 calc R . . C15 C 0.47040(13) 0.57098(10) 0.40196(16) 0.0465(5) Uani 1 1 d . . . H15 H 0.4586 0.5362 0.3745 0.056 Uiso 1 1 calc R . . C16 C 0.54283(12) 0.58031(8) 0.44225(14) 0.0361(4) Uani 1 1 d . . . H16 H 0.5805 0.5522 0.4417 0.043 Uiso 1 1 calc R . . C2 C 0.78928(10) 0.39332(7) 0.75847(13) 0.0262(3) Uani 1 1 d . B . C21 C 0.80227(10) 0.61241(6) 0.67258(13) 0.0253(3) Uani 1 1 d . . . C22 C 0.87641(10) 0.59960(7) 0.64237(14) 0.0317(4) Uani 1 1 d . . . H22 H 0.8891 0.5993 0.5728 0.038 Uiso 1 1 calc R . . C23 C 0.93214(11) 0.58723(8) 0.71336(16) 0.0376(4) Uani 1 1 d . . . H23 H 0.9833 0.5794 0.6926 0.045 Uiso 1 1 calc R . . C24 C 0.91328(12) 0.58622(9) 0.81478(16) 0.0407(5) Uani 1 1 d . . . H24 H 0.9513 0.5772 0.8634 0.049 Uiso 1 1 calc R . . C25 C 0.83947(12) 0.59827(9) 0.84465(15) 0.0387(4) Uani 1 1 d . . . H25 H 0.8266 0.5972 0.9141 0.046 Uiso 1 1 calc R . . C26 C 0.78335(11) 0.61202(8) 0.77454(14) 0.0324(4) Uani 1 1 d . . . H26 H 0.7327 0.621 0.7958 0.039 Uiso 1 1 calc R . . C31 C 0.68714(10) 0.43748(7) 0.85947(12) 0.0267(3) Uani 1 1 d . . . C32 C 0.72218(11) 0.48024(8) 0.91113(14) 0.0312(4) Uani 1 1 d . . . H32 H 0.7764 0.4806 0.9209 0.037 Uiso 1 1 calc R . . C33 C 0.67688(13) 0.52239(8) 0.94807(14) 0.0371(4) Uani 1 1 d . . . H33 H 0.7006 0.552 0.9822 0.045 Uiso 1 1 calc R . . C34 C 0.59804(13) 0.52189(8) 0.93591(15) 0.0393(5) Uani 1 1 d . . . H34 H 0.5677 0.551 0.9617 0.047 Uiso 1 1 calc R . . C35 C 0.56323(12) 0.47896(8) 0.88602(15) 0.0377(4) Uani 1 1 d . . . H35 H 0.5089 0.4784 0.8781 0.045 Uiso 1 1 calc R . . C36 C 0.60762(11) 0.43673(8) 0.84750(14) 0.0319(4) Uani 1 1 d . . . H36 H 0.5837 0.4073 0.813 0.038 Uiso 1 1 calc R . . C41 C 0.8677(8) 0.3368(7) 0.6500(15) 0.031(2) Uani 0.5 1 d P B 1 C42 C 0.8402(4) 0.3356(4) 0.5530(8) 0.052(2) Uani 0.5 1 d P B 1 H42 H 0.7866 0.3404 0.5415 0.062 Uiso 0.5 1 calc PR B 1 C43 C 0.8889(5) 0.3276(3) 0.4712(5) 0.069(2) Uani 0.5 1 d P B 1 H43 H 0.8686 0.326 0.4049 0.082 Uiso 0.5 1 calc PR B 1 C44 C 0.9667(6) 0.3222(3) 0.4871(8) 0.061(2) Uani 0.5 1 d P B 1 H44 H 1 0.3161 0.4315 0.073 Uiso 0.5 1 calc PR B 1 C45 C 0.9957(5) 0.3253(4) 0.5786(8) 0.062(3) Uani 0.5 1 d P B 1 H45 H 1.0499 0.3226 0.5877 0.074 Uiso 0.5 1 calc PR B 1 C46 C 0.9478(5) 0.3325(3) 0.6630(5) 0.0484(15) Uani 0.5 1 d P B 1 H46 H 0.9696 0.3345 0.7285 0.058 Uiso 0.5 1 calc PR B 1 C41' C 0.8864(7) 0.3371(7) 0.6675(14) 0.030(2) Uani 0.5 1 d P B 2 C42' C 0.8704(4) 0.3398(3) 0.5680(8) 0.0437(16) Uani 0.5 1 d P B 2 H42' H 0.8202 0.3487 0.545 0.052 Uiso 0.5 1 calc PR B 2 C43' C 0.9301(6) 0.3292(3) 0.4997(6) 0.0535(19) Uani 0.5 1 d P B 2 H43' H 0.9214 0.3319 0.4293 0.064 Uiso 0.5 1 calc PR B 2 C44' C 1.0024(6) 0.3146(3) 0.5364(9) 0.057(2) Uani 0.5 1 d P B 2 H44' H 1.0435 0.3076 0.491 0.069 Uiso 0.5 1 calc PR B 2 C45' C 1.0139(4) 0.3103(3) 0.6368(6) 0.0567(16) Uani 0.5 1 d P B 2 H45' H 1.0632 0.2998 0.6611 0.068 Uiso 0.5 1 calc PR B 2 C46' C 0.9547(4) 0.3210(3) 0.7057(5) 0.0423(14) Uani 0.5 1 d P B 2 H46' H 0.9623 0.3171 0.7761 0.051 Uiso 0.5 1 calc PR B 2 S5 S 0.8899(3) 0.25 0.2160(2) 0.1312(15) Uani 0.5 2 d SP . 1 C5 C 0.9620(9) 0.25 0.236(2) 0.114(8) Uani 0.5 2 d SP . 1 N5 N 1.0421(4) 0.25 0.2563(6) 0.0493(17) Uani 0.5 2 d SP . 1 C51 C 1.1262(6) 0.25 0.2280(7) 0.068(3) Uani 0.5 2 d SPD . 1 C52 C 1.1807(6) 0.25 0.3003(6) 0.067(2) Uani 0.5 2 d SPD . 1 H52 H 1.1659 0.25 0.3691 0.08 Uiso 0.5 2 calc SPR . 1 C53 C 1.2631(7) 0.25 0.2732(5) 0.095(4) Uani 0.5 2 d SPD . 1 H53 H 1.303 0.25 0.322 0.114 Uiso 0.5 2 calc SPR . 1 C54 C 1.2771(6) 0.25 0.1732(8) 0.091(3) Uani 0.5 2 d SPD . 1 H54 H 1.3295 0.25 0.1525 0.11 Uiso 0.5 2 calc SPR . 1 C55 C 1.2214(6) 0.25 0.0981(6) 0.083(3) Uani 0.5 2 d SPD . 1 H55 H 1.2354 0.25 0.0291 0.099 Uiso 0.5 2 calc SPR . 1 C56 C 1.1458(6) 0.25 0.1267(6) 0.091(3) Uani 0.5 2 d SPD . 1 H56 H 1.1065 0.25 0.077 0.109 Uiso 0.5 2 calc SPR . 1 S S 0.73779(3) 0.25 0.92377(4) 0.02260(12) Uani 1 2 d S . . O1 O 0.75479(13) 0.25 0.81463(15) 0.0391(5) Uani 1 2 d S . . O2 O 0.81078(10) 0.25 0.98102(16) 0.0357(4) Uani 1 2 d S . . O3 O 0.69389(7) 0.29977(4) 0.94861(9) 0.0252(2) Uani 1 1 d . . . O4 O 1.1050(11) 0.25 0.2721(12) 0.155(6) Uani 0.5 2 d SP C 2 O5 O 0.9942(9) 0.25 0.2371(12) 0.115(5) Uani 0.5 2 d SP D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.03609(14) 0.02318(12) 0.03904(14) 0.00759(8) -0.00097(10) 0.00382(9) S1 0.0259(2) 0.0267(2) 0.0429(3) 0.01293(18) -0.00219(19) -0.00449(16) S2 0.0357(2) 0.02072(19) 0.0352(2) 0.00670(16) 0.00894(18) 0.00243(16) N1 0.0244(7) 0.0225(7) 0.0397(8) 0.0089(6) -0.0051(6) -0.0043(5) N2 0.0256(7) 0.0229(7) 0.0279(7) 0.0056(5) -0.0009(6) -0.0025(5) N3 0.0346(8) 0.0204(7) 0.0335(8) 0.0073(6) 0.0063(6) 0.0024(6) N4 0.0419(9) 0.0210(7) 0.0415(9) 0.0074(6) 0.0130(7) 0.0045(6) C1 0.0250(8) 0.0192(7) 0.0301(8) 0.0016(6) -0.0002(7) 0.0004(6) C11 0.0238(8) 0.0274(8) 0.0348(9) 0.0048(7) -0.0014(7) -0.0027(6) C12 0.0441(12) 0.0334(11) 0.102(2) -0.0113(12) -0.0298(13) 0.0093(9) C13 0.0378(12) 0.0643(16) 0.092(2) -0.0133(15) -0.0207(13) 0.0175(12) C14 0.0278(10) 0.0775(16) 0.0381(11) -0.0017(11) -0.0047(9) -0.0102(10) C15 0.0489(13) 0.0507(12) 0.0398(11) -0.0021(9) -0.0098(10) -0.0178(10) C16 0.0393(10) 0.0341(10) 0.0348(10) -0.0021(8) -0.0053(8) -0.0006(8) C2 0.0299(8) 0.0229(8) 0.0257(8) 0.0050(6) -0.0002(7) 0.0018(6) C21 0.0256(8) 0.0205(7) 0.0298(8) 0.0018(6) -0.0023(7) -0.0019(6) C22 0.0287(9) 0.0331(9) 0.0332(9) -0.0012(7) 0.0018(7) 0.0016(7) C23 0.0264(9) 0.0391(10) 0.0471(11) -0.0022(8) -0.0047(8) 0.0053(8) C24 0.0368(10) 0.0428(11) 0.0424(11) 0.0046(9) -0.0142(9) -0.0022(8) C25 0.0396(11) 0.0474(11) 0.0290(9) 0.0026(8) -0.0047(8) -0.0078(9) C26 0.0289(9) 0.0362(10) 0.0322(9) -0.0018(7) -0.0004(7) -0.0028(7) C31 0.0331(9) 0.0242(8) 0.0227(8) 0.0050(6) 0.0026(7) 0.0031(6) C32 0.0331(9) 0.0352(10) 0.0253(8) 0.0027(7) 0.0003(7) -0.0010(7) C33 0.0520(12) 0.0324(9) 0.0269(9) -0.0034(7) 0.0066(8) -0.0022(8) C34 0.0487(12) 0.0358(10) 0.0332(10) 0.0008(8) 0.0139(9) 0.0099(8) C35 0.0322(10) 0.0438(11) 0.0371(10) 0.0056(8) 0.0069(8) 0.0066(8) C36 0.0336(9) 0.0326(9) 0.0294(9) 0.0024(7) 0.0019(7) -0.0009(7) C41 0.021(5) 0.017(2) 0.054(7) 0.002(3) 0.003(4) -0.001(3) C42 0.050(4) 0.066(4) 0.039(3) 0.002(3) 0.003(4) 0.028(4) C43 0.091(6) 0.069(4) 0.045(4) 0.009(3) 0.014(3) 0.042(4) C44 0.068(7) 0.027(3) 0.087(6) 0.000(3) 0.040(5) 0.009(3) C45 0.041(4) 0.043(4) 0.101(9) -0.025(4) 0.031(5) -0.006(3) C46 0.044(4) 0.045(4) 0.056(4) -0.012(3) 0.001(4) -0.001(3) C41' 0.023(6) 0.022(2) 0.046(6) -0.007(3) 0.010(4) -0.003(4) C42' 0.051(4) 0.033(2) 0.047(4) 0.005(2) 0.007(4) 0.012(3) C43' 0.078(7) 0.035(3) 0.047(4) 0.003(2) 0.023(4) 0.012(4) C44' 0.058(5) 0.031(3) 0.083(7) -0.014(3) 0.041(4) 0.001(3) C45' 0.041(3) 0.048(3) 0.081(5) -0.026(3) 0.020(3) -0.007(2) C46' 0.037(3) 0.040(3) 0.050(4) -0.013(3) 0.005(3) 0.001(2) S5 0.128(3) 0.207(5) 0.0589(16) 0 -0.0148(17) 0 C5 0.043(7) 0.24(2) 0.058(8) 0 0.006(6) 0 N5 0.035(4) 0.070(4) 0.043(4) 0 -0.005(3) 0 C51 0.084(7) 0.060(5) 0.061(5) 0 -0.008(5) 0 C52 0.113(8) 0.042(4) 0.046(4) 0 -0.005(5) 0 C53 0.225(15) 0.024(3) 0.035(4) 0 -0.013(6) 0 C54 0.105(8) 0.051(5) 0.118(9) 0 -0.006(7) 0 C55 0.106(8) 0.097(7) 0.044(4) 0 -0.010(5) 0 C56 0.117(9) 0.105(8) 0.052(5) 0 -0.027(6) 0 S 0.0247(3) 0.0149(2) 0.0282(3) 0 0.0010(2) 0 O1 0.0620(13) 0.0212(9) 0.0342(10) 0 0.0172(9) 0 O2 0.0251(9) 0.0190(8) 0.0629(13) 0 -0.0098(9) 0 O3 0.0274(6) 0.0184(5) 0.0299(6) -0.0018(4) -0.0017(5) 0.0043(4) O4 0.191(13) 0.052(5) 0.221(15) 0 0.092(13) 0 O5 0.155(18) 0.137(9) 0.055(7) 0 0.017(14) 0 #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu S2 2.1770(5) . ? Cu S1 2.1811(5) . ? S1 C1 1.7109(17) . ? S2 C2 1.7116(17) . ? N1 C1 1.344(2) . ? N1 C11 1.425(2) . ? N1 H1 0.88 . ? N2 C1 1.340(2) . ? N2 C21 1.423(2) . ? N2 H2 0.88 . ? N3 C2 1.338(2) . ? N3 C31 1.427(2) . ? N3 H3 0.88 . ? N4 C2 1.338(2) . ? N4 C41 1.42(2) . ? N4 C41' 1.472(18) . ? N4 H4 0.88 . ? C11 C12 1.372(3) . ? C11 C16 1.374(3) . ? C12 C13 1.394(3) . ? C12 H12 0.95 . ? C13 C14 1.356(4) . ? C13 H13 0.95 . ? C14 C15 1.365(3) . ? C14 H14 0.95 . ? C15 C16 1.386(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C21 C22 1.385(2) . ? C21 C26 1.395(3) . ? C22 C23 1.385(3) . ? C22 H22 0.95 . ? C23 C24 1.387(3) . ? C23 H23 0.95 . ? C24 C25 1.374(3) . ? C24 H24 0.95 . ? C25 C26 1.390(3) . ? C25 H25 0.95 . ? C26 H26 0.95 . ? C31 C36 1.390(3) . ? C31 C32 1.392(3) . ? C32 C33 1.388(3) . ? C32 H32 0.95 . ? C33 C34 1.379(3) . ? C33 H33 0.95 . ? C34 C35 1.383(3) . ? C34 H34 0.95 . ? C35 C36 1.388(3) . ? C35 H35 0.95 . ? C36 H36 0.95 . ? C41 C42 1.376(17) . ? C41 C46 1.406(13) . ? C42 C43 1.391(13) . ? C42 H42 0.95 . ? C43 C44 1.374(11) . ? C43 H43 0.95 . ? C44 C45 1.319(16) . ? C44 H44 0.95 . ? C45 C46 1.408(11) . ? C45 H45 0.95 . ? C46 H46 0.95 . ? C41' C46' 1.350(12) . ? C41' C42' 1.353(18) . ? C42' C43' 1.402(13) . ? C42' H42' 0.95 . ? C43' C44' 1.394(14) . ? C43' H43' 0.95 . ? C44' C45' 1.353(13) . ? C44' H44' 0.95 . ? C45' C46' 1.402(10) . ? C45' H45' 0.95 . ? C46' H46' 0.95 . ? S5 C5 1.281(18) . ? C5 N5 1.416(18) . ? N5 C51 1.509(13) . ? C51 C52 1.348(12) . ? C51 C56 1.389(11) . ? C52 C53 1.476(12) . ? C52 H52 0.95 . ? C53 C54 1.351(11) . ? C53 H53 0.95 . ? C54 C55 1.391(11) . ? C54 H54 0.95 . ? C55 C56 1.366(11) . ? C55 H55 0.95 . ? C56 H56 0.95 . ? S O3 1.4752(11) . ? S O3 1.4752(11) 8_565 ? S O2 1.4785(19) . ? S O1 1.480(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Cu S1 162.18(2) . . ? C1 S1 Cu 104.76(6) . . ? C2 S2 Cu 106.48(6) . . ? C1 N1 C11 127.18(14) . . ? C1 N1 H1 116.4 . . ? C11 N1 H1 116.4 . . ? C1 N2 C21 127.30(14) . . ? C1 N2 H2 116.3 . . ? C21 N2 H2 116.3 . . ? C2 N3 C31 126.90(14) . . ? C2 N3 H3 116.6 . . ? C31 N3 H3 116.6 . . ? C2 N4 C41 122.7(7) . . ? C2 N4 C41' 124.7(7) . . ? C2 N4 H4 118.7 . . ? C41 N4 H4 118.7 . . ? C41' N4 H4 114.2 . . ? N2 C1 N1 114.11(15) . . ? N2 C1 S1 124.60(13) . . ? N1 C1 S1 121.29(13) . . ? C12 C11 C16 119.60(18) . . ? C12 C11 N1 118.24(17) . . ? C16 C11 N1 122.13(16) . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.5(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C11 C16 C15 119.58(19) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? N4 C2 N3 115.71(15) . . ? N4 C2 S2 119.49(13) . . ? N3 C2 S2 124.79(13) . . ? C22 C21 C26 119.96(16) . . ? C22 C21 N2 118.54(16) . . ? C26 C21 N2 121.35(16) . . ? C21 C22 C23 120.11(18) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C22 C23 C24 120.06(19) . . ? C22 C23 H23 120 . . ? C24 C23 H23 120 . . ? C25 C24 C23 119.81(18) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.84(19) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 119.20(18) . . ? C25 C26 H26 120.4 . . ? C21 C26 H26 120.4 . . ? C36 C31 C32 120.03(16) . . ? C36 C31 N3 118.14(16) . . ? C32 C31 N3 121.72(16) . . ? C33 C32 C31 119.11(18) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C34 C33 C32 120.99(19) . . ? C34 C33 H33 119.5 . . ? C32 C33 H33 119.5 . . ? C33 C34 C35 119.81(18) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 120.06(19) . . ? C34 C35 H35 120 . . ? C36 C35 H35 120 . . ? C35 C36 C31 119.98(18) . . ? C35 C36 H36 120 . . ? C31 C36 H36 120 . . ? C42 C41 C46 117.2(15) . . ? C42 C41 N4 123.9(9) . . ? C46 C41 N4 118.8(11) . . ? C41 C42 C43 121.6(9) . . ? C41 C42 H42 119.2 . . ? C43 C42 H42 119.2 . . ? C44 C43 C42 119.5(7) . . ? C44 C43 H43 120.3 . . ? C42 C43 H43 120.3 . . ? C45 C44 C43 120.8(8) . . ? C45 C44 H44 119.6 . . ? C43 C44 H44 119.6 . . ? C44 C45 C46 121.1(8) . . ? C44 C45 H45 119.5 . . ? C46 C45 H45 119.5 . . ? C41 C46 C45 119.7(11) . . ? C41 C46 H46 120.1 . . ? C45 C46 H46 120.1 . . ? C46' C41' C42' 124.1(13) . . ? C46' C41' N4 119.2(13) . . ? C42' C41' N4 116.1(8) . . ? C41' C42' C43' 118.2(9) . . ? C41' C42' H42' 120.9 . . ? C43' C42' H42' 120.9 . . ? C44' C43' C42' 119.1(7) . . ? C44' C43' H43' 120.4 . . ? C42' C43' H43' 120.4 . . ? C45' C44' C43' 119.9(7) . . ? C45' C44' H44' 120 . . ? C43' C44' H44' 120 . . ? C44' C45' C46' 121.4(7) . . ? C44' C45' H45' 119.3 . . ? C46' C45' H45' 119.3 . . ? C41' C46' C45' 117.0(10) . . ? C41' C46' H46' 121.5 . . ? C45' C46' H46' 121.5 . . ? S5 C5 N5 179(3) . . ? C5 N5 C51 154.7(17) . . ? C52 C51 C56 121.3(9) . . ? C52 C51 N5 120.2(8) . . ? C56 C51 N5 118.6(8) . . ? C51 C52 C53 120.4(8) . . ? C51 C52 H52 119.8 . . ? C53 C52 H52 119.8 . . ? C54 C53 C52 114.5(8) . . ? C54 C53 H53 122.7 . . ? C52 C53 H53 122.7 . . ? C53 C54 C55 125.4(9) . . ? C53 C54 H54 117.3 . . ? C55 C54 H54 117.3 . . ? C56 C55 C54 118.0(8) . . ? C56 C55 H55 121 . . ? C54 C55 H55 121 . . ? C55 C56 C51 120.3(8) . . ? C55 C56 H56 119.9 . . ? C51 C56 H56 119.8 . . ? O3 S O3 111.45(10) . 8_565 ? O3 S O2 109.14(7) . . ? O3 S O2 109.14(7) 8_565 . ? O3 S O1 108.81(7) . . ? O3 S O1 108.81(7) 8_565 . ? O2 S O1 109.47(13) . . ? #===END data_gb0708 _database_code_depnum_ccdc_archive 'CCDC 671528' _audit_creation_date 2007-10-22T21:12:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C56 H54 Cl2 Cu2 N10 S4' _chemical_formula_moiety 'C52 H48 Cl2 Cu2 N8 S4, 2(C2 H3 N)' _chemical_formula_weight 1193.31 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall -p_2ybc 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 12.34050(10) _cell_length_b 12.17870(10) _cell_length_c 18.4154(2) _cell_angle_alpha 90 _cell_angle_beta 92.5510(10) _cell_angle_gamma 90 _cell_volume 2764.93(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16350 _cell_measurement_theta_min 3.1734 _cell_measurement_theta_max 34.8466 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.90726 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0448631435 _diffrn_orient_matrix_ub_12 0.0334014528 _diffrn_orient_matrix_ub_13 0.0083070008 _diffrn_orient_matrix_ub_21 0.0357273011 _diffrn_orient_matrix_ub_22 0.038545954 _diffrn_orient_matrix_ub_23 0.0171577189 _diffrn_orient_matrix_ub_31 0.0042535834 _diffrn_orient_matrix_ub_32 0.0280627856 _diffrn_orient_matrix_ub_33 -0.0334614329 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_unetI/netI 0.0574 _diffrn_reflns_number 50097 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 34.95 _diffrn_reflns_theta_full 34 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 11555 _reflns_number_gt 7715 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0345P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 11555 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0703 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.451 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.044974(12) 0.568366(12) 0.561391(8) 0.01625(4) Uani 1 1 d . . . Cl1 Cl 0.22337(2) 0.62716(2) 0.567695(15) 0.01719(6) Uani 1 1 d . . . S1 S 0.01935(2) 0.38097(2) 0.563046(15) 0.01387(6) Uani 1 1 d . . . C1 C 0.13465(9) 0.31250(9) 0.54075(6) 0.0147(2) Uani 1 1 d . . . N11 N 0.13865(8) 0.20223(8) 0.54350(6) 0.0173(2) Uani 1 1 d . . . H11 H 0.1999 0.1695 0.5336 0.021 Uiso 1 1 calc R . . C111 C 0.04840(10) 0.13544(9) 0.56165(6) 0.0171(2) Uani 1 1 d . . . C112 C -0.04721(10) 0.13730(10) 0.51916(7) 0.0190(2) Uani 1 1 d . . . H112 H -0.0535 0.1821 0.4769 0.023 Uiso 1 1 calc R . . C113 C -0.13375(11) 0.07273(11) 0.53922(8) 0.0261(3) Uani 1 1 d . . . H113 H -0.2 0.074 0.5109 0.031 Uiso 1 1 calc R . . C114 C -0.12379(13) 0.00628(11) 0.60059(8) 0.0315(3) Uani 1 1 d . . . H114 H -0.1835 -0.0368 0.6146 0.038 Uiso 1 1 calc R . . C115 C -0.02732(13) 0.00313(11) 0.64095(8) 0.0304(3) Uani 1 1 d . . . H115 H -0.0203 -0.0434 0.6823 0.036 Uiso 1 1 calc R . . C116 C 0.05972(12) 0.06724(10) 0.62189(7) 0.0229(3) Uani 1 1 d . . . H116 H 0.1264 0.0645 0.6497 0.028 Uiso 1 1 calc R . . N12 N 0.22228(8) 0.36872(8) 0.52232(5) 0.01599(19) Uani 1 1 d . . . H12 H 0.219 0.4404 0.5277 0.019 Uiso 1 1 calc R . . C121 C 0.32043(10) 0.32700(10) 0.49499(6) 0.0161(2) Uani 1 1 d . . . C122 C 0.31919(10) 0.24770(10) 0.44067(6) 0.0189(2) Uani 1 1 d . . . H122 H 0.2524 0.218 0.422 0.023 Uiso 1 1 calc R . . C123 C 0.41689(11) 0.21243(11) 0.41410(7) 0.0222(3) Uani 1 1 d . . . H123 H 0.4168 0.1566 0.3781 0.027 Uiso 1 1 calc R . . C124 C 0.51414(11) 0.25750(12) 0.43935(7) 0.0249(3) Uani 1 1 d . . . H124 H 0.5805 0.2332 0.4206 0.03 Uiso 1 1 calc R . . C125 C 0.51426(11) 0.33872(12) 0.49248(7) 0.0256(3) Uani 1 1 d . . . H125 H 0.5808 0.3709 0.5094 0.031 Uiso 1 1 calc R . . C126 C 0.41752(10) 0.37283(11) 0.52086(7) 0.0206(2) Uani 1 1 d . . . H126 H 0.4178 0.4273 0.5578 0.025 Uiso 1 1 calc R . . S2 S -0.07118(2) 0.64118(3) 0.641556(16) 0.01870(6) Uani 1 1 d . . . C2 C -0.00239(10) 0.71740(9) 0.70576(6) 0.0150(2) Uani 1 1 d . . . N21 N -0.05249(8) 0.77613(8) 0.75658(5) 0.01514(19) Uani 1 1 d . . . H21 H -0.0096 0.8066 0.7903 0.018 Uiso 1 1 calc R . . C211 C -0.16571(10) 0.79551(10) 0.76297(6) 0.0160(2) Uani 1 1 d . . . C212 C -0.19591(11) 0.90153(11) 0.78293(6) 0.0199(2) Uani 1 1 d . . . H212 H -0.1425 0.9574 0.7892 0.024 Uiso 1 1 calc R . . C213 C -0.30444(11) 0.92504(12) 0.79353(7) 0.0255(3) Uani 1 1 d . . . H213 H -0.325 0.997 0.8074 0.031 Uiso 1 1 calc R . . C214 C -0.38241(11) 0.84447(13) 0.78410(7) 0.0278(3) Uani 1 1 d . . . H214 H -0.4565 0.861 0.791 0.033 Uiso 1 1 calc R . . C215 C -0.35194(11) 0.73907(12) 0.76449(7) 0.0256(3) Uani 1 1 d . . . H215 H -0.4056 0.6836 0.7579 0.031 Uiso 1 1 calc R . . C216 C -0.24352(10) 0.71407(11) 0.75441(7) 0.0211(3) Uani 1 1 d . . . H216 H -0.2231 0.6416 0.7417 0.025 Uiso 1 1 calc R . . N22 N 0.10699(8) 0.72143(9) 0.70635(5) 0.0178(2) Uani 1 1 d . . . H22 H 0.1386 0.676 0.6767 0.021 Uiso 1 1 calc R . . C221 C 0.17722(9) 0.79079(10) 0.74938(6) 0.0163(2) Uani 1 1 d . . . C222 C 0.24756(10) 0.86014(11) 0.71416(7) 0.0199(2) Uani 1 1 d . . . H222 H 0.2476 0.8611 0.6626 0.024 Uiso 1 1 calc R . . C223 C 0.31739(11) 0.92762(11) 0.75459(7) 0.0237(3) Uani 1 1 d . . . H223 H 0.3666 0.9738 0.7307 0.028 Uiso 1 1 calc R . . C224 C 0.31588(11) 0.92822(11) 0.83003(7) 0.0243(3) Uani 1 1 d . . . H224 H 0.3625 0.9761 0.8575 0.029 Uiso 1 1 calc R . . C225 C 0.24631(11) 0.85890(11) 0.86490(7) 0.0233(3) Uani 1 1 d . . . H225 H 0.2452 0.8594 0.9165 0.028 Uiso 1 1 calc R . . C226 C 0.17776(10) 0.78829(10) 0.82494(6) 0.0188(2) Uani 1 1 d . . . H226 H 0.1318 0.7389 0.849 0.023 Uiso 1 1 calc R . . N101 N 0.35971(12) 0.44533(12) 0.07395(7) 0.0390(3) Uani 1 1 d . . . C101 C 0.44771(13) 0.42559(12) 0.08836(8) 0.0305(3) Uani 1 1 d . . . C102 C 0.56108(14) 0.39924(16) 0.10734(10) 0.0441(4) Uani 1 1 d . . . H10A H 0.5681 0.3203 0.1168 0.066 Uiso 1 1 calc R . . H10B H 0.5849 0.4402 0.151 0.066 Uiso 1 1 calc R . . H10C H 0.6062 0.4196 0.067 0.066 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 0.01447(7) 0.01629(7) 0.01823(7) -0.00212(6) 0.00349(5) 0.00022(6) Cl1 0.01360(12) 0.01977(13) 0.01850(13) -0.00306(10) 0.00430(10) -0.00176(10) S1 0.01243(12) 0.01474(12) 0.01466(13) -0.00022(10) 0.00296(10) 0.00008(10) C1 0.0149(5) 0.0165(5) 0.0127(5) -0.0005(4) 0.0014(4) -0.0010(4) N11 0.0154(5) 0.0137(4) 0.0231(5) 0.0003(4) 0.0042(4) 0.0016(4) C111 0.0196(6) 0.0135(5) 0.0187(5) -0.0021(4) 0.0069(4) 0.0001(5) C112 0.0212(6) 0.0164(5) 0.0198(6) -0.0025(4) 0.0045(5) -0.0006(5) C113 0.0217(6) 0.0232(6) 0.0342(7) -0.0118(6) 0.0096(5) -0.0054(5) C114 0.0377(8) 0.0185(6) 0.0402(8) -0.0067(6) 0.0230(7) -0.0101(6) C115 0.0459(9) 0.0187(6) 0.0278(7) 0.0032(5) 0.0169(7) -0.0020(6) C116 0.0311(7) 0.0177(6) 0.0203(6) 0.0005(5) 0.0048(5) 0.0022(5) N12 0.0136(5) 0.0143(4) 0.0202(5) -0.0016(4) 0.0036(4) -0.0008(4) C121 0.0141(5) 0.0177(5) 0.0169(5) 0.0020(4) 0.0041(4) 0.0009(4) C122 0.0166(6) 0.0205(6) 0.0197(6) -0.0026(5) 0.0013(5) 0.0001(5) C123 0.0238(6) 0.0228(6) 0.0206(6) -0.0023(5) 0.0059(5) 0.0042(5) C124 0.0176(6) 0.0306(7) 0.0273(7) -0.0003(5) 0.0081(5) 0.0037(5) C125 0.0135(6) 0.0340(7) 0.0297(7) -0.0032(6) 0.0033(5) -0.0021(5) C126 0.0170(6) 0.0236(6) 0.0213(6) -0.0038(5) 0.0027(5) -0.0024(5) S2 0.01366(13) 0.02412(15) 0.01851(14) -0.00650(11) 0.00291(11) -0.00012(12) C2 0.0156(5) 0.0155(5) 0.0139(5) 0.0014(4) 0.0025(4) 0.0019(4) N21 0.0136(5) 0.0187(5) 0.0131(4) -0.0033(4) 0.0014(4) 0.0006(4) C211 0.0149(5) 0.0213(6) 0.0119(5) 0.0007(4) 0.0019(4) 0.0034(5) C212 0.0214(6) 0.0233(6) 0.0151(6) -0.0013(4) 0.0010(5) 0.0054(5) C213 0.0255(7) 0.0325(7) 0.0186(6) -0.0043(5) 0.0005(5) 0.0132(6) C214 0.0167(6) 0.0473(9) 0.0195(6) -0.0031(6) 0.0020(5) 0.0103(6) C215 0.0165(6) 0.0382(8) 0.0225(6) -0.0012(6) 0.0044(5) -0.0011(6) C216 0.0186(6) 0.0260(6) 0.0190(6) 0.0004(5) 0.0047(5) 0.0013(5) N22 0.0143(5) 0.0227(5) 0.0166(5) -0.0060(4) 0.0036(4) 0.0004(4) C221 0.0131(5) 0.0189(5) 0.0169(5) -0.0018(4) 0.0014(4) 0.0021(4) C222 0.0183(6) 0.0250(6) 0.0166(6) 0.0013(5) 0.0036(4) 0.0003(5) C223 0.0173(6) 0.0245(6) 0.0296(7) 0.0035(5) 0.0033(5) -0.0021(5) C224 0.0171(6) 0.0275(7) 0.0279(7) -0.0065(5) -0.0018(5) -0.0008(5) C225 0.0192(6) 0.0332(7) 0.0175(6) -0.0055(5) 0.0006(5) 0.0027(5) C226 0.0155(6) 0.0238(6) 0.0172(6) 0.0007(5) 0.0032(4) 0.0017(5) N101 0.0384(8) 0.0449(8) 0.0337(7) -0.0036(6) 0.0010(6) -0.0018(7) C101 0.0347(8) 0.0298(7) 0.0271(7) -0.0056(6) 0.0037(6) -0.0049(7) C102 0.0338(9) 0.0452(10) 0.0533(11) -0.0101(8) 0.0003(8) -0.0018(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.2823(3) . ? Cu1 S1 2.3044(3) . ? Cu1 Cl1 2.3130(3) . ? Cu1 S1 2.4698(3) 3_566 ? Cu1 Cu1 2.9823(3) 3_566 ? S1 C1 1.7148(12) . ? S1 Cu1 2.4698(3) 3_566 ? C1 N12 1.3365(15) . ? C1 N11 1.3447(15) . ? N11 C111 1.4307(15) . ? N11 H11 0.88 . ? C111 C112 1.3866(18) . ? C111 C116 1.3880(17) . ? C112 C113 1.3894(18) . ? C112 H112 0.95 . ? C113 C114 1.391(2) . ? C113 H113 0.95 . ? C114 C115 1.376(2) . ? C114 H114 0.95 . ? C115 C116 1.386(2) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? N12 C121 1.4258(15) . ? N12 H12 0.88 . ? C121 C126 1.3868(17) . ? C121 C122 1.3900(17) . ? C122 C123 1.3893(17) . ? C122 H122 0.95 . ? C123 C124 1.3814(19) . ? C123 H123 0.95 . ? C124 C125 1.3913(19) . ? C124 H124 0.95 . ? C125 C126 1.3879(18) . ? C125 H125 0.95 . ? C126 H126 0.95 . ? S2 C2 1.7003(12) . ? C2 N21 1.3495(14) . ? C2 N22 1.3503(15) . ? N21 C211 1.4270(15) . ? N21 H21 0.88 . ? C211 C216 1.3846(18) . ? C211 C212 1.3975(17) . ? C212 C213 1.3919(18) . ? C212 H212 0.95 . ? C213 C214 1.380(2) . ? C213 H213 0.95 . ? C214 C215 1.390(2) . ? C214 H214 0.95 . ? C215 C216 1.3927(18) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? N22 C221 1.4253(16) . ? N22 H22 0.88 . ? C221 C226 1.3915(16) . ? C221 C222 1.3919(17) . ? C222 C223 1.3839(19) . ? C222 H222 0.95 . ? C223 C224 1.3902(19) . ? C223 H223 0.95 . ? C224 C225 1.3825(19) . ? C224 H224 0.95 . ? C225 C226 1.3933(18) . ? C225 H225 0.95 . ? C226 H226 0.95 . ? N101 C101 1.132(2) . ? C101 C102 1.462(2) . ? C102 H10A 0.98 . ? C102 H10B 0.98 . ? C102 H10C 0.98 . ? 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 106.603(12) . . ? S2 Cu1 Cl1 118.101(12) . . ? S1 Cu1 Cl1 115.899(12) . . ? S2 Cu1 S1 108.538(12) . 3_566 ? S1 Cu1 S1 102.771(10) . 3_566 ? Cl1 Cu1 S1 103.599(11) . 3_566 ? S2 Cu1 Cu1 118.953(11) . 3_566 ? S1 Cu1 Cu1 53.870(8) . 3_566 ? Cl1 Cu1 Cu1 122.155(10) . 3_566 ? S1 Cu1 Cu1 48.901(8) 3_566 3_566 ? C1 S1 Cu1 111.26(4) . . ? C1 S1 Cu1 97.77(4) . 3_566 ? Cu1 S1 Cu1 77.229(10) . 3_566 ? N12 C1 N11 119.50(11) . . ? N12 C1 S1 120.07(9) . . ? N11 C1 S1 120.40(9) . . ? C1 N11 C111 123.29(10) . . ? C1 N11 H11 118.4 . . ? C111 N11 H11 118.4 . . ? C112 C111 C116 120.91(12) . . ? C112 C111 N11 120.70(11) . . ? C116 C111 N11 118.37(12) . . ? C111 C112 C113 119.05(12) . . ? C111 C112 H112 120.5 . . ? C113 C112 H112 120.5 . . ? C112 C113 C114 120.27(14) . . ? C112 C113 H113 119.9 . . ? C114 C113 H113 119.9 . . ? C115 C114 C113 119.89(13) . . ? C115 C114 H114 120.1 . . ? C113 C114 H114 120.1 . . ? C114 C115 C116 120.62(13) . . ? C114 C115 H115 119.7 . . ? C116 C115 H115 119.7 . . ? C115 C116 C111 119.21(14) . . ? C115 C116 H116 120.4 . . ? C111 C116 H116 120.4 . . ? C1 N12 C121 128.08(10) . . ? C1 N12 H12 116 . . ? C121 N12 H12 116 . . ? C126 C121 C122 120.57(11) . . ? C126 C121 N12 118.02(11) . . ? C122 C121 N12 121.29(11) . . ? C123 C122 C121 119.10(12) . . ? C123 C122 H122 120.4 . . ? C121 C122 H122 120.4 . . ? C124 C123 C122 120.87(12) . . ? C124 C123 H123 119.6 . . ? C122 C123 H123 119.6 . . ? C123 C124 C125 119.54(12) . . ? C123 C124 H124 120.2 . . ? C125 C124 H124 120.2 . . ? C126 C125 C124 120.24(13) . . ? C126 C125 H125 119.9 . . ? C124 C125 H125 119.9 . . ? C121 C126 C125 119.65(12) . . ? C121 C126 H126 120.2 . . ? C125 C126 H126 120.2 . . ? C2 S2 Cu1 110.70(4) . . ? N21 C2 N22 117.64(10) . . ? N21 C2 S2 122.80(9) . . ? N22 C2 S2 119.56(9) . . ? C2 N21 C211 128.71(10) . . ? C2 N21 H21 115.6 . . ? C211 N21 H21 115.6 . . ? C216 C211 C212 120.01(11) . . ? C216 C211 N21 123.27(11) . . ? C212 C211 N21 116.62(11) . . ? C213 C212 C211 119.77(13) . . ? C213 C212 H212 120.1 . . ? C211 C212 H212 120.1 . . ? C214 C213 C212 120.40(13) . . ? C214 C213 H213 119.8 . . ? C212 C213 H213 119.8 . . ? C213 C214 C215 119.63(12) . . ? C213 C214 H214 120.2 . . ? C215 C214 H214 120.2 . . ? C214 C215 C216 120.61(13) . . ? C214 C215 H215 119.7 . . ? C216 C215 H215 119.7 . . ? C211 C216 C215 119.58(12) . . ? C211 C216 H216 120.2 . . ? C215 C216 H216 120.2 . . ? C2 N22 C221 127.51(10) . . ? C2 N22 H22 116.2 . . ? C221 N22 H22 116.2 . . ? C226 C221 C222 120.25(11) . . ? C226 C221 N22 121.25(11) . . ? C222 C221 N22 118.49(10) . . ? C223 C222 C221 119.74(11) . . ? C223 C222 H222 120.1 . . ? C221 C222 H222 120.1 . . ? C222 C223 C224 120.33(12) . . ? C222 C223 H223 119.8 . . ? C224 C223 H223 119.8 . . ? C225 C224 C223 119.82(12) . . ? C225 C224 H224 120.1 . . ? C223 C224 H224 120.1 . . ? C224 C225 C226 120.43(12) . . ? C224 C225 H225 119.8 . . ? C226 C225 H225 119.8 . . ? C221 C226 C225 119.37(12) . . ? C221 C226 H226 120.3 . . ? C225 C226 H226 120.3 . . ? N101 C101 C102 179.5(2) . . ? C101 C102 H10A 109.5 . . ? C101 C102 H10B 109.5 . . ? H10A C102 H10B 109.5 . . ? C101 C102 H10C 109.5 . . ? H10A C102 H10C 109.5 . . ? H10B C102 H10C 109.5 . . ? #===END data_gb0709 _database_code_depnum_ccdc_archive 'CCDC 671529' _audit_creation_date 2007-10-30T14:38:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C52 H48 Br2 Cu2 N8 S4' _chemical_formula_moiety 'C52 H48 Br2 Cu2 N8 S4' _chemical_formula_weight 1200.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall -P_2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8704(2) _cell_length_b 12.21780(10) _cell_length_c 18.0909(3) _cell_angle_alpha 90 _cell_angle_beta 106.2140(10) _cell_angle_gamma 90 _cell_volume 2519.37(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 23066 _cell_measurement_theta_min 3.3103 _cell_measurement_theta_max 34.766 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.582 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.87288 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 -0.0042971716 _diffrn_orient_matrix_ub_12 -0.0498921465 _diffrn_orient_matrix_ub_13 -0.0206352556 _diffrn_orient_matrix_ub_21 -0.0499722425 _diffrn_orient_matrix_ub_22 -0.0147886805 _diffrn_orient_matrix_ub_23 0.0119620458 _diffrn_orient_matrix_ub_31 -0.0368346004 _diffrn_orient_matrix_ub_32 0.0257281303 _diffrn_orient_matrix_ub_33 -0.0331130517 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_unetI/netI 0.058 _diffrn_reflns_number 89483 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 34.92 _diffrn_reflns_theta_full 34.5 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.97 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 10683 _reflns_number_gt 7071 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0282P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 10683 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0602 _refine_ls_wR_factor_gt 0.0531 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.457 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.083 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.498550(14) 0.441420(14) 0.423746(10) 0.01679(4) Uani 1 1 d . . . Br1 Br 0.668513(11) 0.402107(12) 0.377815(8) 0.01769(4) Uani 1 1 d . . . S1 S 0.44348(3) 0.62029(3) 0.440007(19) 0.01439(6) Uani 1 1 d . . . C1 C 0.55697(11) 0.70841(11) 0.44275(7) 0.0147(2) Uani 1 1 d . . . N11 N 0.54449(10) 0.81639(10) 0.44997(7) 0.0193(2) Uani 1 1 d . . . H11 H 0.6061 0.8574 0.4516 0.023 Uiso 1 1 calc R . . C111 C 0.44088(12) 0.87173(11) 0.45525(9) 0.0197(3) Uani 1 1 d . . . C112 C 0.39346(13) 0.85129(13) 0.51521(9) 0.0254(3) Uani 1 1 d . . . H112 H 0.4273 0.7975 0.5528 0.03 Uiso 1 1 calc R . . C113 C 0.29563(14) 0.90998(15) 0.52026(12) 0.0361(4) Uani 1 1 d . . . H113 H 0.2612 0.895 0.5607 0.043 Uiso 1 1 calc R . . C114 C 0.24811(14) 0.99022(15) 0.46652(13) 0.0429(5) Uani 1 1 d . . . H114 H 0.1819 1.031 0.4704 0.051 Uiso 1 1 calc R . . C115 C 0.29730(16) 1.01075(15) 0.40735(12) 0.0424(5) Uani 1 1 d . . . H115 H 0.2649 1.0661 0.3707 0.051 Uiso 1 1 calc R . . C116 C 0.39355(15) 0.95144(13) 0.40072(10) 0.0306(4) Uani 1 1 d . . . H116 H 0.4266 0.9651 0.3595 0.037 Uiso 1 1 calc R . . N12 N 0.65989(9) 0.67127(10) 0.43762(6) 0.0167(2) Uani 1 1 d . . . H12 H 0.6702 0.6 0.4372 0.02 Uiso 1 1 calc R . . C121 C 0.75521(12) 0.74056(12) 0.43266(8) 0.0179(3) Uani 1 1 d . . . C122 C 0.86071(12) 0.73839(13) 0.48976(9) 0.0217(3) Uani 1 1 d . . . H122 H 0.8704 0.6925 0.5335 0.026 Uiso 1 1 calc R . . C123 C 0.95208(13) 0.80421(14) 0.48221(9) 0.0277(3) Uani 1 1 d . . . H123 H 1.0251 0.8029 0.5209 0.033 Uiso 1 1 calc R . . C124 C 0.93794(14) 0.87151(15) 0.41909(10) 0.0327(4) Uani 1 1 d . . . H124 H 1.001 0.9163 0.4143 0.039 Uiso 1 1 calc R . . C125 C 0.83123(15) 0.87370(16) 0.36244(10) 0.0356(4) Uani 1 1 d . . . H125 H 0.821 0.9204 0.3191 0.043 Uiso 1 1 calc R . . C126 C 0.74004(13) 0.80786(14) 0.36922(9) 0.0268(3) Uani 1 1 d . . . H126 H 0.6671 0.8088 0.3304 0.032 Uiso 1 1 calc R . . S2 S 0.31770(3) 0.36810(3) 0.36899(2) 0.02141(8) Uani 1 1 d . . . C2 C 0.31310(11) 0.29448(12) 0.28890(8) 0.0167(3) Uani 1 1 d . . . N21 N 0.21601(10) 0.23978(10) 0.24923(7) 0.0184(2) Uani 1 1 d . . . H21 H 0.2192 0.2092 0.2058 0.022 Uiso 1 1 calc R . . C211 C 0.10933(11) 0.22577(12) 0.26944(8) 0.0179(3) Uani 1 1 d . . . C212 C 0.05902(13) 0.12216(13) 0.25773(8) 0.0225(3) Uani 1 1 d . . . H212 H 0.0959 0.0653 0.2372 0.027 Uiso 1 1 calc R . . C213 C -0.04500(14) 0.10180(15) 0.27605(9) 0.0289(4) Uani 1 1 d . . . H213 H -0.0798 0.0312 0.2674 0.035 Uiso 1 1 calc R . . C214 C -0.09804(13) 0.18362(15) 0.30668(8) 0.0296(4) Uani 1 1 d . . . H214 H -0.1678 0.1688 0.3208 0.035 Uiso 1 1 calc R . . C215 C -0.04952(12) 0.28745(15) 0.31683(8) 0.0258(3) Uani 1 1 d . . . H215 H -0.0866 0.3438 0.3376 0.031 Uiso 1 1 calc R . . C216 C 0.05335(12) 0.31012(13) 0.29682(8) 0.0209(3) Uani 1 1 d . . . H216 H 0.0847 0.3822 0.3018 0.025 Uiso 1 1 calc R . . N22 N 0.41002(10) 0.28730(11) 0.26373(7) 0.0202(2) Uani 1 1 d . . . H22 H 0.4659 0.3349 0.2836 0.024 Uiso 1 1 calc R . . C221 C 0.43338(12) 0.21279(12) 0.20930(8) 0.0191(3) Uani 1 1 d . . . C222 C 0.54011(13) 0.15740(13) 0.23052(9) 0.0245(3) Uani 1 1 d . . . H222 H 0.5929 0.1688 0.2801 0.029 Uiso 1 1 calc R . . C223 C 0.56940(14) 0.08579(14) 0.17956(9) 0.0280(3) Uani 1 1 d . . . H223 H 0.6432 0.0496 0.1935 0.034 Uiso 1 1 calc R . . C224 C 0.49069(15) 0.06696(14) 0.10796(9) 0.0287(3) Uani 1 1 d . . . H224 H 0.5094 0.0159 0.0736 0.034 Uiso 1 1 calc R . . C225 C 0.38522(14) 0.12243(14) 0.08672(9) 0.0266(3) Uani 1 1 d . . . H225 H 0.3314 0.1089 0.0378 0.032 Uiso 1 1 calc R . . C226 C 0.35700(12) 0.19784(14) 0.13628(8) 0.0227(3) Uani 1 1 d . . . H226 H 0.2863 0.2387 0.1204 0.027 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 0.01412(8) 0.01585(8) 0.02048(9) -0.00234(6) 0.00494(6) -0.00228(6) Br1 0.01459(6) 0.01945(7) 0.02016(7) -0.00119(5) 0.00674(5) -0.00104(5) S1 0.01219(14) 0.01412(16) 0.01697(15) -0.00040(12) 0.00423(12) -0.00192(11) C1 0.0152(6) 0.0148(6) 0.0141(6) 0.0000(5) 0.0041(5) -0.0016(5) N11 0.0163(5) 0.0131(6) 0.0301(7) -0.0008(5) 0.0089(5) -0.0032(4) C111 0.0153(6) 0.0122(6) 0.0292(8) -0.0043(5) 0.0019(5) -0.0016(5) C112 0.0245(7) 0.0182(7) 0.0355(9) -0.0038(6) 0.0118(6) -0.0022(6) C113 0.0273(8) 0.0261(9) 0.0611(12) -0.0170(8) 0.0225(8) -0.0059(7) C114 0.0166(7) 0.0269(10) 0.0790(15) -0.0202(9) 0.0032(8) -0.0008(7) C115 0.0328(9) 0.0209(9) 0.0574(12) -0.0030(8) -0.0140(9) 0.0066(7) C116 0.0319(8) 0.0201(8) 0.0330(9) 0.0003(7) -0.0024(7) 0.0007(7) N12 0.0143(5) 0.0157(6) 0.0211(6) -0.0010(4) 0.0068(4) -0.0028(4) C121 0.0165(6) 0.0192(7) 0.0203(7) -0.0053(5) 0.0088(5) -0.0048(5) C122 0.0167(6) 0.0250(8) 0.0236(7) -0.0018(6) 0.0063(5) -0.0008(6) C123 0.0173(7) 0.0345(9) 0.0317(8) -0.0091(7) 0.0072(6) -0.0059(6) C124 0.0264(8) 0.0386(10) 0.0382(9) -0.0086(8) 0.0172(7) -0.0172(7) C125 0.0363(9) 0.0421(11) 0.0317(9) 0.0068(8) 0.0149(7) -0.0144(8) C126 0.0235(7) 0.0353(9) 0.0216(7) 0.0018(6) 0.0061(6) -0.0096(7) S2 0.01434(15) 0.0280(2) 0.02244(18) -0.01005(14) 0.00608(13) -0.00608(14) C2 0.0147(6) 0.0167(7) 0.0178(6) 0.0009(5) 0.0029(5) -0.0023(5) N21 0.0156(5) 0.0230(6) 0.0167(6) -0.0054(5) 0.0046(4) -0.0056(5) C211 0.0134(6) 0.0254(8) 0.0138(6) 0.0013(5) 0.0018(5) -0.0057(5) C212 0.0267(7) 0.0248(8) 0.0155(7) -0.0008(6) 0.0049(6) -0.0082(6) C213 0.0300(8) 0.0361(9) 0.0198(7) 0.0007(7) 0.0058(6) -0.0173(7) C214 0.0199(7) 0.0495(11) 0.0201(7) 0.0013(7) 0.0067(6) -0.0117(7) C215 0.0157(7) 0.0406(10) 0.0206(7) -0.0018(6) 0.0039(5) -0.0013(6) C216 0.0150(6) 0.0265(8) 0.0197(7) 0.0003(6) 0.0021(5) -0.0020(6) N22 0.0138(5) 0.0248(7) 0.0220(6) -0.0068(5) 0.0053(5) -0.0053(5) C221 0.0157(6) 0.0219(7) 0.0209(7) -0.0034(6) 0.0071(5) -0.0038(5) C222 0.0182(7) 0.0293(8) 0.0242(8) -0.0055(6) 0.0029(6) -0.0003(6) C223 0.0233(7) 0.0305(9) 0.0309(8) -0.0032(7) 0.0090(6) 0.0032(6) C224 0.0342(9) 0.0293(9) 0.0267(8) -0.0083(7) 0.0152(7) -0.0051(7) C225 0.0273(8) 0.0345(9) 0.0184(7) -0.0063(6) 0.0071(6) -0.0105(7) C226 0.0169(6) 0.0326(9) 0.0188(7) -0.0008(6) 0.0052(5) -0.0036(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.2814(4) . ? Cu1 S1 2.3232(4) . ? Cu1 Br1 2.4347(2) . ? Cu1 S1 2.4840(4) 3_666 ? S1 C1 1.7144(13) . ? S1 Cu1 2.4840(4) 3_666 ? C1 N12 1.3306(17) . ? C1 N11 1.3380(18) . ? N11 C111 1.4299(18) . ? N11 H11 0.88 . ? C111 C112 1.377(2) . ? C111 C116 1.388(2) . ? C112 C113 1.389(2) . ? C112 H112 0.95 . ? C113 C114 1.385(3) . ? C113 H113 0.95 . ? C114 C115 1.378(3) . ? C114 H114 0.95 . ? C115 C116 1.386(3) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? N12 C121 1.4359(17) . ? N12 H12 0.88 . ? C121 C126 1.382(2) . ? C121 C122 1.3834(19) . ? C122 C123 1.387(2) . ? C122 H122 0.95 . ? C123 C124 1.379(2) . ? C123 H123 0.95 . ? C124 C125 1.389(2) . ? C124 H124 0.95 . ? C125 C126 1.381(2) . ? C125 H125 0.95 . ? C126 H126 0.95 . ? S2 C2 1.6932(14) . ? C2 N21 1.3521(17) . ? C2 N22 1.3533(17) . ? N21 C211 1.4231(17) . ? N21 H21 0.88 . ? C211 C216 1.390(2) . ? C211 C212 1.390(2) . ? C212 C213 1.387(2) . ? C212 H212 0.95 . ? C213 C214 1.377(2) . ? C213 H213 0.95 . ? C214 C215 1.384(2) . ? C214 H214 0.95 . ? C215 C216 1.395(2) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? N22 C221 1.4239(18) . ? N22 H22 0.88 . ? C221 C226 1.3899(19) . ? C221 C222 1.392(2) . ? C222 C223 1.384(2) . ? C222 H222 0.95 . ? C223 C224 1.388(2) . ? C223 H223 0.95 . ? C224 C225 1.380(2) . ? C224 H224 0.95 . ? C225 C226 1.390(2) . ? C225 H225 0.95 . ? C226 H226 0.95 . ? 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 99.233(14) . . ? S2 Cu1 Br1 122.908(12) . . ? S1 Cu1 Br1 121.202(11) . . ? S2 Cu1 S1 106.143(14) . 3_666 ? S1 Cu1 S1 99.769(12) . 3_666 ? Br1 Cu1 S1 104.621(10) . 3_666 ? C1 S1 Cu1 110.35(5) . . ? C1 S1 Cu1 99.45(5) . 3_666 ? Cu1 S1 Cu1 80.231(12) . 3_666 ? N12 C1 N11 118.16(12) . . ? N12 C1 S1 120.88(10) . . ? N11 C1 S1 120.96(10) . . ? C1 N11 C111 126.40(12) . . ? C1 N11 H11 116.8 . . ? C111 N11 H11 116.8 . . ? C112 C111 C116 120.90(14) . . ? C112 C111 N11 121.02(13) . . ? C116 C111 N11 117.97(14) . . ? C111 C112 C113 119.41(16) . . ? C111 C112 H112 120.3 . . ? C113 C112 H112 120.3 . . ? C114 C113 C112 120.22(18) . . ? C114 C113 H113 119.9 . . ? C112 C113 H113 119.9 . . ? C115 C114 C113 119.75(16) . . ? C115 C114 H114 120.1 . . ? C113 C114 H114 120.1 . . ? C114 C115 C116 120.69(17) . . ? C114 C115 H115 119.7 . . ? C116 C115 H115 119.7 . . ? C115 C116 C111 119.01(18) . . ? C115 C116 H116 120.5 . . ? C111 C116 H116 120.5 . . ? C1 N12 C121 123.92(12) . . ? C1 N12 H12 118 . . ? C121 N12 H12 118 . . ? C126 C121 C122 120.82(13) . . ? C126 C121 N12 118.72(12) . . ? C122 C121 N12 120.45(13) . . ? C121 C122 C123 119.01(14) . . ? C121 C122 H122 120.5 . . ? C123 C122 H122 120.5 . . ? C124 C123 C122 120.63(14) . . ? C124 C123 H123 119.7 . . ? C122 C123 H123 119.7 . . ? C123 C124 C125 119.83(15) . . ? C123 C124 H124 120.1 . . ? C125 C124 H124 120.1 . . ? C126 C125 C124 119.92(16) . . ? C126 C125 H125 120 . . ? C124 C125 H125 120 . . ? C125 C126 C121 119.78(14) . . ? C125 C126 H126 120.1 . . ? C121 C126 H126 120.1 . . ? C2 S2 Cu1 112.44(5) . . ? N21 C2 N22 117.91(12) . . ? N21 C2 S2 122.40(10) . . ? N22 C2 S2 119.68(10) . . ? C2 N21 C211 127.65(12) . . ? C2 N21 H21 116.2 . . ? C211 N21 H21 116.2 . . ? C216 C211 C212 120.10(13) . . ? C216 C211 N21 123.40(13) . . ? C212 C211 N21 116.45(13) . . ? C213 C212 C211 119.99(15) . . ? C213 C212 H212 120 . . ? C211 C212 H212 120 . . ? C214 C213 C212 120.22(15) . . ? C214 C213 H213 119.9 . . ? C212 C213 H213 119.9 . . ? C213 C214 C215 119.89(14) . . ? C213 C214 H214 120.1 . . ? C215 C214 H214 120.1 . . ? C214 C215 C216 120.64(15) . . ? C214 C215 H215 119.7 . . ? C216 C215 H215 119.7 . . ? C211 C216 C215 119.04(14) . . ? C211 C216 H216 120.5 . . ? C215 C216 H216 120.5 . . ? C2 N22 C221 128.47(12) . . ? C2 N22 H22 115.8 . . ? C221 N22 H22 115.8 . . ? C226 C221 C222 120.00(14) . . ? C226 C221 N22 122.68(13) . . ? C222 C221 N22 117.26(12) . . ? C223 C222 C221 120.14(14) . . ? C223 C222 H222 119.9 . . ? C221 C222 H222 119.9 . . ? C222 C223 C224 119.83(15) . . ? C222 C223 H223 120.1 . . ? C224 C223 H223 120.1 . . ? C225 C224 C223 120.00(15) . . ? C225 C224 H224 120 . . ? C223 C224 H224 120 . . ? C224 C225 C226 120.60(14) . . ? C224 C225 H225 119.7 . . ? C226 C225 H225 119.7 . . ? C221 C226 C225 119.29(14) . . ? C221 C226 H226 120.4 . . ? C225 C226 H226 120.4 . . ? #===END data_gb0706 _database_code_depnum_ccdc_archive 'CCDC 671530' _audit_creation_date 2007-10-23T09:52:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C52 H48 Cu2 I2 N8 S4' _chemical_formula_moiety 'C52 H48 Cu2 I2 N8 S4' _chemical_formula_weight 1294.1 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.9993(2) _cell_length_b 12.1609(3) _cell_length_c 18.4265(4) _cell_angle_alpha 90 _cell_angle_beta 106.447(2) _cell_angle_gamma 90 _cell_volume 2578.81(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15898 _cell_measurement_theta_min 3.2736 _cell_measurement_theta_max 37.5398 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour off_white _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.88664 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4738 _diffrn_orient_matrix_ub_11 0.0002351482 _diffrn_orient_matrix_ub_12 0.0577066302 _diffrn_orient_matrix_ub_13 0.0059980104 _diffrn_orient_matrix_ub_21 -0.0499474424 _diffrn_orient_matrix_ub_22 -0.0050887804 _diffrn_orient_matrix_ub_23 0.0130950138 _diffrn_orient_matrix_ub_31 0.0361217086 _diffrn_orient_matrix_ub_32 -0.0074970462 _diffrn_orient_matrix_ub_33 0.0374800575 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_unetI/netI 0.0628 _diffrn_reflns_number 56745 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 37.66 _diffrn_reflns_theta_full 37 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measurement_device_type ; Oxford Diffraction Gemini diffractometer ; _diffrn_measurement_method '\w scans' _reflns_number_total 13255 _reflns_number_gt 7367 _reflns_threshold_expression I>2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0521P)^2^+1.2215P] 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_number_reflns 13255 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1054 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.563 _refine_diff_density_min -3.283 _refine_diff_density_rms 0.131 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.49925(3) 0.44123(3) 0.425376(18) 0.02432(7) Uani 1 1 d . . . I1 I 0.682320(14) 0.397016(19) 0.381174(11) 0.03721(6) Uani 1 1 d . . . S1 S 0.44664(5) 0.62272(5) 0.44064(4) 0.02227(12) Uani 1 1 d . . . C1 C 0.5581(2) 0.7125(2) 0.44331(14) 0.0279(5) Uani 1 1 d . B . N11 N 0.5439(2) 0.8211(2) 0.44788(15) 0.0383(6) Uani 1 1 d . . . H11 H 0.6008 0.8638 0.4434 0.046 Uiso 0.5 1 calc PR A 1 H13 H 0.6076 0.8612 0.458 0.046 Uiso 0.5 1 calc PR A 2 C111 C 0.4320(4) 0.8792(4) 0.4608(3) 0.0156(8) Uiso 0.5 1 d P B 1 C112 C 0.3885(4) 0.8527(4) 0.5207(3) 0.0173(8) Uiso 0.5 1 d P B 1 H112 H 0.4239 0.797 0.5558 0.021 Uiso 0.5 1 calc PR B 1 C113 C 0.2923(4) 0.9091(4) 0.5281(3) 0.0237(9) Uiso 0.5 1 d P B 1 H113 H 0.2608 0.8916 0.5686 0.028 Uiso 0.5 1 calc PR B 1 C114 C 0.2407(5) 0.9919(5) 0.4767(3) 0.0270(10) Uiso 0.5 1 d P B 1 H114 H 0.1751 1.0307 0.4826 0.032 Uiso 0.5 1 calc PR B 1 C115 C 0.2866(6) 1.0178(5) 0.4156(4) 0.0312(12) Uiso 0.5 1 d P B 1 H115 H 0.2515 1.0728 0.3798 0.037 Uiso 0.5 1 calc PR B 1 C116 C 0.3831(5) 0.9615(4) 0.4096(3) 0.0253(10) Uiso 0.5 1 d P B 1 H116 H 0.4164 0.9791 0.37 0.03 Uiso 0.5 1 calc PR B 1 C131 C 0.4506(5) 0.8724(4) 0.4394(3) 0.0233(10) Uiso 0.5 1 d P B 2 C132 C 0.3942(5) 0.8609(5) 0.4938(4) 0.0290(11) Uiso 0.5 1 d P B 2 H132 H 0.4228 0.811 0.5345 0.035 Uiso 0.5 1 calc PR B 2 C133 C 0.2938(6) 0.9231(6) 0.4893(4) 0.0389(13) Uiso 0.5 1 d P B 2 H133 H 0.2518 0.9125 0.5254 0.047 Uiso 0.5 1 calc PR B 2 C134 C 0.2564(6) 0.9996(6) 0.4325(4) 0.0357(13) Uiso 0.5 1 d P B 2 H134 H 0.1916 1.0452 0.4313 0.043 Uiso 0.5 1 calc PR B 2 C135 C 0.3132(7) 1.0100(7) 0.3771(5) 0.0507(17) Uiso 0.5 1 d P B 2 H135 H 0.2851 1.0603 0.3366 0.061 Uiso 0.5 1 calc PR B 2 C136 C 0.4116(6) 0.9467(5) 0.3806(4) 0.0365(13) Uiso 0.5 1 d P B 2 H136 H 0.4514 0.9545 0.3431 0.044 Uiso 0.5 1 calc PR B 2 N12 N 0.66162(19) 0.6753(2) 0.44101(12) 0.0302(5) Uani 1 1 d . . . H12 H 0.6787 0.6048 0.4432 0.036 Uiso 0.5 1 calc PR B 1 H14 H 0.6661 0.6031 0.4408 0.036 Uiso 0.5 1 calc PR B 2 C121 C 0.7448(5) 0.7602(5) 0.4346(3) 0.0213(10) Uiso 0.5 1 d P B 1 C122 C 0.8498(5) 0.7621(6) 0.4913(3) 0.0302(12) Uiso 0.5 1 d P B 1 H122 H 0.8611 0.717 0.5349 0.036 Uiso 0.5 1 calc PR B 1 C123 C 0.9378(6) 0.8311(6) 0.4832(4) 0.0366(13) Uiso 0.5 1 d P B 1 H123 H 1.0102 0.8326 0.5213 0.044 Uiso 0.5 1 calc PR B 1 C124 C 0.9208(6) 0.8973(6) 0.4205(3) 0.0354(12) Uiso 0.5 1 d P B 1 H124 H 0.9806 0.9453 0.4156 0.042 Uiso 0.5 1 calc PR B 1 C125 C 0.8171(5) 0.8934(5) 0.3651(3) 0.0317(11) Uiso 0.5 1 d P B 1 H125 H 0.8059 0.9381 0.3213 0.038 Uiso 0.5 1 calc PR B 1 C126 C 0.7289(5) 0.8260(5) 0.3719(3) 0.0234(9) Uiso 0.5 1 d P B 1 H126 H 0.657 0.8248 0.3333 0.028 Uiso 0.5 1 calc PR B 1 C141 C 0.7676(4) 0.7290(4) 0.4388(3) 0.0162(9) Uiso 0.5 1 d P B 2 C142 C 0.8674(4) 0.7254(5) 0.4975(3) 0.0167(8) Uiso 0.5 1 d P B 2 H142 H 0.8715 0.6821 0.5411 0.02 Uiso 0.5 1 calc PR B 2 C143 C 0.9631(4) 0.7866(5) 0.4919(3) 0.0221(9) Uiso 0.5 1 d P B 2 H143 H 1.0327 0.7844 0.5324 0.026 Uiso 0.5 1 calc PR B 2 C144 C 0.9591(5) 0.8503(5) 0.4290(3) 0.0269(10) Uiso 0.5 1 d P B 2 H144 H 1.0247 0.8925 0.4268 0.032 Uiso 0.5 1 calc PR B 2 C145 C 0.8589(5) 0.8517(5) 0.3694(3) 0.0304(11) Uiso 0.5 1 d P B 2 H145 H 0.8556 0.8942 0.3256 0.036 Uiso 0.5 1 calc PR B 2 C146 C 0.7618(5) 0.7903(5) 0.3736(3) 0.0274(10) Uiso 0.5 1 d P B 2 H146 H 0.6928 0.7904 0.3325 0.033 Uiso 0.5 1 calc PR B 2 S2 S 0.31955(5) 0.36721(6) 0.36935(4) 0.02962(14) Uani 1 1 d . . . C2 C 0.3147(2) 0.2935(2) 0.29019(13) 0.0243(5) Uani 1 1 d . . . N21 N 0.21831(19) 0.2406(2) 0.25038(13) 0.0318(5) Uani 1 1 d . . . H21 H 0.2213 0.2107 0.2075 0.038 Uiso 1 1 calc R . . C211 C 0.1116(2) 0.2271(3) 0.26934(14) 0.0348(7) Uani 1 1 d . . . C212 C 0.0621(3) 0.1222(3) 0.25818(16) 0.0417(8) Uani 1 1 d . . . H212 H 0.0989 0.0645 0.2388 0.05 Uiso 1 1 calc R . . C213 C -0.0414(3) 0.1032(4) 0.27580(19) 0.0540(11) Uani 1 1 d . . . H213 H -0.0759 0.0323 0.268 0.065 Uiso 1 1 calc R . . C214 C -0.0946(3) 0.1868(4) 0.3045(2) 0.0581(12) Uani 1 1 d . . . H214 H -0.1639 0.1727 0.3182 0.07 Uiso 1 1 calc R . . C215 C -0.0465(2) 0.2910(4) 0.31327(18) 0.0498(10) Uani 1 1 d . . . H215 H -0.0839 0.3488 0.3321 0.06 Uiso 1 1 calc R . . C216 C 0.0565(2) 0.3122(3) 0.29470(15) 0.0366(7) Uani 1 1 d . . . H216 H 0.0882 0.3843 0.2995 0.044 Uiso 1 1 calc R . . N22 N 0.41077(18) 0.2859(2) 0.26656(12) 0.0288(5) Uani 1 1 d . . . H22 H 0.4668 0.3324 0.2876 0.035 Uiso 1 1 calc R . . C221 C 0.4343(2) 0.2134(3) 0.21255(16) 0.0370(7) Uani 1 1 d . . . C222 C 0.5399(3) 0.1576(3) 0.2329(2) 0.0454(8) Uani 1 1 d . . . H222 H 0.5913 0.167 0.2823 0.055 Uiso 1 1 calc R . . C223 C 0.5708(3) 0.0889(4) 0.1821(3) 0.0635(13) Uani 1 1 d . . . H223 H 0.6443 0.0534 0.1958 0.076 Uiso 1 1 calc R . . C224 C 0.4943(3) 0.0720(5) 0.1113(3) 0.0756(16) Uani 1 1 d . . . H224 H 0.5136 0.0224 0.0769 0.091 Uiso 1 1 calc R . . C225 C 0.3896(3) 0.1274(5) 0.0906(2) 0.0732(16) Uani 1 1 d . . . H225 H 0.3373 0.1155 0.0419 0.088 Uiso 1 1 calc R . . C226 C 0.3595(3) 0.2003(4) 0.14005(17) 0.0545(11) Uani 1 1 d . . . H226 H 0.2889 0.2406 0.1246 0.065 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 0.01584(12) 0.02703(16) 0.03201(16) -0.00273(12) 0.00988(11) -0.00456(11) I1 0.01807(7) 0.05807(14) 0.04073(11) -0.01345(9) 0.01680(7) -0.01093(8) S1 0.0169(2) 0.0205(3) 0.0275(3) -0.0004(2) 0.0032(2) -0.00632(19) C1 0.0264(12) 0.0309(13) 0.0227(11) 0.0041(10) 0.0006(9) -0.0140(10) N11 0.0359(13) 0.0261(12) 0.0433(14) 0.0076(10) -0.0043(11) -0.0167(10) N12 0.0255(10) 0.0402(13) 0.0265(10) -0.0032(9) 0.0100(8) -0.0185(9) S2 0.0176(3) 0.0424(4) 0.0311(3) -0.0088(3) 0.0105(2) -0.0104(2) C2 0.0190(10) 0.0339(13) 0.0193(10) 0.0062(9) 0.0045(8) -0.0030(9) N21 0.0207(10) 0.0521(15) 0.0215(10) -0.0030(10) 0.0043(8) -0.0092(10) C211 0.0201(11) 0.064(2) 0.0175(11) 0.0091(12) 0.0002(9) -0.0116(12) C212 0.0335(15) 0.067(2) 0.0201(12) 0.0092(13) -0.0002(11) -0.0215(14) C213 0.0379(17) 0.088(3) 0.0298(15) 0.0202(17) -0.0004(13) -0.0318(19) C214 0.0240(14) 0.108(4) 0.0389(17) 0.033(2) 0.0042(13) -0.0193(18) C215 0.0176(12) 0.095(3) 0.0344(15) 0.0269(17) 0.0040(11) 0.0030(15) C216 0.0161(10) 0.064(2) 0.0265(13) 0.0139(13) 0.0015(9) -0.0033(12) N22 0.0165(9) 0.0453(14) 0.0237(10) -0.0027(9) 0.0044(8) -0.0026(9) C221 0.0177(11) 0.062(2) 0.0287(13) -0.0096(13) 0.0025(10) -0.0004(12) C222 0.0193(12) 0.063(2) 0.0465(18) -0.0207(16) -0.0021(12) 0.0026(13) C223 0.0229(14) 0.086(3) 0.078(3) -0.040(2) 0.0090(16) 0.0005(17) C224 0.0342(18) 0.129(4) 0.068(3) -0.059(3) 0.0220(18) -0.014(2) C225 0.0275(15) 0.151(5) 0.0406(19) -0.048(2) 0.0084(14) -0.010(2) C226 0.0182(12) 0.118(4) 0.0263(13) -0.0131(18) 0.0046(11) 0.0037(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 2.2946(7) . ? Cu1 S1 2.3343(7) . ? Cu1 S1 2.4928(7) 3_666 ? Cu1 I1 2.6060(3) . ? S1 C1 1.716(3) . ? S1 Cu1 2.4928(7) 3_666 ? C1 N12 1.334(4) . ? C1 N11 1.337(4) . ? N11 C131 1.252(6) . ? N11 C111 1.594(6) . ? N11 H11 0.88 . ? N11 H13 0.88 . ? C111 C112 1.386(7) . ? C111 C116 1.387(7) . ? C112 C113 1.383(7) . ? C112 H112 0.95 . ? C113 C114 1.401(8) . ? C113 H113 0.95 . ? C114 C115 1.420(8) . ? C114 H114 0.95 . ? C115 C116 1.377(8) . ? C115 H115 0.95 . ? C116 H116 0.95 . ? C131 C132 1.366(9) . ? C131 C136 1.387(8) . ? C132 C133 1.406(9) . ? C132 H132 0.95 . ? C133 C134 1.377(10) . ? C133 H133 0.95 . ? C134 C135 1.384(11) . ? C134 H134 0.95 . ? C135 C136 1.395(10) . ? C135 H135 0.95 . ? C136 H136 0.95 . ? N12 C141 1.440(5) . ? N12 C121 1.464(6) . ? N12 H12 0.88 . ? N12 H14 0.88 . ? C121 C126 1.373(8) . ? C121 C122 1.391(8) . ? C122 C123 1.390(9) . ? C122 H122 0.95 . ? C123 C124 1.375(9) . ? C123 H123 0.95 . ? C124 C125 1.369(9) . ? C124 H124 0.95 . ? C125 C126 1.372(8) . ? C125 H125 0.95 . ? C126 H126 0.95 . ? C141 C142 1.368(7) . ? C141 C146 1.399(7) . ? C142 C143 1.397(7) . ? C142 H142 0.95 . ? C143 C144 1.385(8) . ? C143 H143 0.95 . ? C144 C145 1.380(8) . ? C144 H144 0.95 . ? C145 C146 1.405(8) . ? C145 H145 0.95 . ? C146 H146 0.95 . ? S2 C2 1.699(3) . ? C2 N21 1.345(3) . ? C2 N22 1.346(3) . ? N21 C211 1.429(3) . ? N21 H21 0.88 . ? C211 C216 1.379(5) . ? C211 C212 1.398(5) . ? C212 C213 1.390(5) . ? C212 H212 0.95 . ? C213 C214 1.383(7) . ? C213 H213 0.95 . ? C214 C215 1.383(6) . ? C214 H214 0.95 . ? C215 C216 1.397(4) . ? C215 H215 0.95 . ? C216 H216 0.95 . ? N22 C221 1.416(4) . ? N22 H22 0.88 . ? C221 C226 1.392(4) . ? C221 C222 1.392(4) . ? C222 C223 1.382(5) . ? C222 H222 0.95 . ? C223 C224 1.382(6) . ? C223 H223 0.95 . ? C224 C225 1.380(6) . ? C224 H224 0.95 . ? C225 C226 1.390(5) . ? C225 H225 0.95 . ? C226 H226 0.95 . ? 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 99.98(3) . . ? S2 Cu1 S1 105.74(3) . 3_666 ? S1 Cu1 S1 100.32(2) . 3_666 ? S2 Cu1 I1 123.12(2) . . ? S1 Cu1 I1 120.89(2) . . ? S1 Cu1 I1 103.824(19) 3_666 . ? C1 S1 Cu1 111.71(11) . . ? C1 S1 Cu1 100.83(9) . 3_666 ? Cu1 S1 Cu1 79.68(2) . 3_666 ? N12 C1 N11 118.2(2) . . ? N12 C1 S1 120.6(2) . . ? N11 C1 S1 121.2(2) . . ? C131 N11 C1 127.5(3) . . ? C1 N11 C111 125.1(3) . . ? C131 N11 H11 112.6 . . ? C1 N11 H11 117.5 . . ? C111 N11 H11 117.5 . . ? C131 N11 H13 116.2 . . ? C1 N11 H13 116.2 . . ? C111 N11 H13 116.1 . . ? C112 C111 C116 121.8(5) . . ? C112 C111 N11 122.6(4) . . ? C116 C111 N11 115.5(4) . . ? C113 C112 C111 118.5(5) . . ? C113 C112 H112 120.7 . . ? C111 C112 H112 120.7 . . ? C112 C113 C114 120.7(5) . . ? C112 C113 H113 119.7 . . ? C114 C113 H113 119.7 . . ? C113 C114 C115 120.0(5) . . ? C113 C114 H114 120 . . ? C115 C114 H114 120 . . ? C116 C115 C114 118.5(6) . . ? C116 C115 H115 120.7 . . ? C114 C115 H115 120.7 . . ? C115 C116 C111 120.5(5) . . ? C115 C116 H116 119.8 . . ? C111 C116 H116 119.8 . . ? N11 C131 C132 117.9(5) . . ? N11 C131 C136 121.0(6) . . ? C132 C131 C136 120.8(6) . . ? C131 C132 C133 119.8(6) . . ? C131 C132 H132 120.1 . . ? C133 C132 H132 120.1 . . ? C134 C133 C132 119.8(7) . . ? C134 C133 H133 120.1 . . ? C132 C133 H133 120.1 . . ? C133 C134 C135 120.0(7) . . ? C133 C134 H134 120 . . ? C135 C134 H134 120 . . ? C134 C135 C136 120.2(7) . . ? C134 C135 H135 119.9 . . ? C136 C135 H135 119.9 . . ? C131 C136 C135 119.3(7) . . ? C131 C136 H136 120.3 . . ? C135 C136 H136 120.3 . . ? C1 N12 C141 133.3(3) . . ? C1 N12 C121 115.2(3) . . ? C1 N12 H12 122.4 . . ? C141 N12 H12 104.3 . . ? C121 N12 H12 122.4 . . ? C1 N12 H14 113.4 . . ? C141 N12 H14 113.4 . . ? C121 N12 H14 131.3 . . ? C126 C121 C122 120.3(5) . . ? C126 C121 N12 122.9(4) . . ? C122 C121 N12 116.3(5) . . ? C123 C122 C121 118.9(6) . . ? C123 C122 H122 120.6 . . ? C121 C122 H122 120.6 . . ? C124 C123 C122 120.5(6) . . ? C124 C123 H123 119.8 . . ? C122 C123 H123 119.8 . . ? C125 C124 C123 119.6(6) . . ? C125 C124 H124 120.2 . . ? C123 C124 H124 120.2 . . ? C124 C125 C126 120.9(6) . . ? C124 C125 H125 119.5 . . ? C126 C125 H125 119.5 . . ? C125 C126 C121 119.9(5) . . ? C125 C126 H126 120.1 . . ? C121 C126 H126 120.1 . . ? C142 C141 C146 121.0(5) . . ? C142 C141 N12 123.1(4) . . ? C146 C141 N12 115.8(4) . . ? C141 C142 C143 118.6(5) . . ? C141 C142 H142 120.7 . . ? C143 C142 H142 120.7 . . ? C144 C143 C142 121.7(5) . . ? C144 C143 H143 119.1 . . ? C142 C143 H143 119.1 . . ? C145 C144 C143 119.3(5) . . ? C145 C144 H144 120.4 . . ? C143 C144 H144 120.4 . . ? C144 C145 C146 120.0(5) . . ? C144 C145 H145 120 . . ? C146 C145 H145 120 . . ? C141 C146 C145 119.4(5) . . ? C141 C146 H146 120.3 . . ? C145 C146 H146 120.3 . . ? C2 S2 Cu1 113.14(9) . . ? N21 C2 N22 118.3(2) . . ? N21 C2 S2 122.43(19) . . ? N22 C2 S2 119.31(19) . . ? C2 N21 C211 127.8(2) . . ? C2 N21 H21 116.1 . . ? C211 N21 H21 116.1 . . ? C216 C211 C212 120.7(3) . . ? C216 C211 N21 123.0(3) . . ? C212 C211 N21 116.2(3) . . ? C213 C212 C211 119.2(4) . . ? C213 C212 H212 120.4 . . ? C211 C212 H212 120.4 . . ? C214 C213 C212 120.5(4) . . ? C214 C213 H213 119.7 . . ? C212 C213 H213 119.7 . . ? C215 C214 C213 119.7(3) . . ? C215 C214 H214 120.2 . . ? C213 C214 H214 120.2 . . ? C214 C215 C216 120.7(4) . . ? C214 C215 H215 119.7 . . ? C216 C215 H215 119.7 . . ? C211 C216 C215 119.1(3) . . ? C211 C216 H216 120.4 . . ? C215 C216 H216 120.4 . . ? C2 N22 C221 129.0(2) . . ? C2 N22 H22 115.5 . . ? C221 N22 H22 115.5 . . ? C226 C221 C222 119.6(3) . . ? C226 C221 N22 122.9(3) . . ? C222 C221 N22 117.4(2) . . ? C223 C222 C221 120.6(3) . . ? C223 C222 H222 119.7 . . ? C221 C222 H222 119.7 . . ? C224 C223 C222 119.8(4) . . ? C224 C223 H223 120.1 . . ? C222 C223 H223 120.1 . . ? C225 C224 C223 119.8(4) . . ? C225 C224 H224 120.1 . . ? C223 C224 H224 120.1 . . ? C224 C225 C226 121.0(3) . . ? C224 C225 H225 119.5 . . ? C226 C225 H225 119.5 . . ? C225 C226 C221 119.1(3) . . ? C225 C226 H226 120.5 . . ? C221 C226 H226 120.5 . . ? #===END