# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ss _database_code_depnum_ccdc_archive 'CCDC 923406' #TrackingRef '923406.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H48 Br2 Cu N4 O6 Si2' _chemical_formula_weight 816.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.3107(4) _cell_length_b 16.6058(4) _cell_length_c 11.7604(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.501(2) _cell_angle_gamma 90.00 _cell_volume 3526.86(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5506 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.57 _exptl_crystal_description BLOCK _exptl_crystal_colour black _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1676 _exptl_absorpt_coefficient_mu 2.997 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3658 _exptl_absorpt_correction_T_max 0.5718 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Breeze CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29229 _diffrn_reflns_av_R_equivalents 0.1117 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3840 _reflns_number_gt 2834 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2200P)^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_extinction_coef ? _refine_ls_number_reflns 3840 _refine_ls_number_parameters 196 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0859 _refine_ls_wR_factor_ref 0.2887 _refine_ls_wR_factor_gt 0.2753 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si1 Si 0.35308(9) 0.24534(12) 0.69378(15) 0.0263(5) Uani 1 1 d . . . Cu1 Cu 0.0000 0.32059(6) 0.7500 0.0204(3) Uani 1 2 d S . . Br1 Br 0.0000 0.47638(5) 0.7500 0.0271(3) Uani 1 2 d S . . Br2 Br 0.0000 0.0587(2) 0.7500 0.1928(19) Uani 1 2 d S . . O1 O 0.2475(16) 0.0691(16) 0.920(2) 0.252(11) Uani 1 1 d . . . H1M H 0.2676 0.0358 0.9694 0.303 Uiso 1 1 calc R . . O2 O 0.1562(5) -0.0056(3) 1.1253(7) 0.075(3) Uani 1 1 d D . . H2 H 0.1639 -0.0038 1.1977 0.113 Uiso 1 1 calc R . . N1 N 0.1045(3) 0.3027(3) 0.7148(5) 0.0230(11) Uani 1 1 d . . . N2 N 0.4585(3) 0.2003(3) 1.0804(5) 0.0243(12) Uani 1 1 d . . . C1 C 0.1579(3) 0.3586(4) 0.7410(6) 0.0284(14) Uani 1 1 d . . . H1A H 0.1445 0.4102 0.7659 0.034 Uiso 1 1 calc R . . C2 C 0.2308(4) 0.3444(4) 0.7332(6) 0.0293(15) Uani 1 1 d . . . H2A H 0.2665 0.3859 0.7517 0.035 Uiso 1 1 calc R . . C3 C 0.2524(3) 0.2698(4) 0.6984(5) 0.0262(14) Uani 1 1 d . . . C4 C 0.1973(4) 0.2126(5) 0.6705(6) 0.0295(15) Uani 1 1 d . . . H4A H 0.2094 0.1604 0.6461 0.035 Uiso 1 1 calc R . . C5 C 0.1239(4) 0.2317(4) 0.6784(6) 0.0297(15) Uani 1 1 d . . . H5A H 0.0866 0.1922 0.6568 0.036 Uiso 1 1 calc R . . C6 C 0.4578(4) 0.1420(5) 1.0023(6) 0.0318(16) Uani 1 1 d . . . H6A H 0.4790 0.0911 1.0253 0.038 Uiso 1 1 calc R . . C7 C 0.4266(4) 0.1547(5) 0.8876(6) 0.0346(17) Uani 1 1 d . . . H7A H 0.4264 0.1118 0.8343 0.042 Uiso 1 1 calc R . . C8 C 0.3961(3) 0.2267(4) 0.8490(5) 0.0244(14) Uani 1 1 d . . . C9 C 0.3981(4) 0.2863(4) 0.9330(6) 0.0338(16) Uani 1 1 d . . . H9A H 0.3774 0.3377 0.9119 0.041 Uiso 1 1 calc R . . C10 C 0.4292(4) 0.2722(4) 1.0459(6) 0.0328(16) Uani 1 1 d . . . H10A H 0.4301 0.3143 1.1008 0.039 Uiso 1 1 calc R . . C11 C 0.3589(4) 0.1513(5) 0.6090(6) 0.0387(18) Uani 1 1 d . . . H11A H 0.4109 0.1386 0.6071 0.046 Uiso 1 1 calc R . . H11B H 0.3326 0.1590 0.5301 0.046 Uiso 1 1 calc R . . H11C H 0.3361 0.1067 0.6452 0.046 Uiso 1 1 calc R . . C12 C 0.3985(4) 0.3341(6) 0.6403(7) 0.0409(18) Uani 1 1 d . . . H12A H 0.4505 0.3215 0.6376 0.049 Uiso 1 1 calc R . . H12B H 0.3958 0.3798 0.6921 0.049 Uiso 1 1 calc R . . H12C H 0.3732 0.3479 0.5627 0.049 Uiso 1 1 calc R . . C13 C 0.2245(11) -0.0023(17) 1.0845(19) 0.174(10) Uani 1 1 d DU . . H13A H 0.2506 0.0474 1.1115 0.209 Uiso 1 1 calc R . . H13B H 0.2155 -0.0032 1.0000 0.209 Uiso 1 1 calc R . . H13C H 0.2548 -0.0489 1.1135 0.209 Uiso 1 1 calc R . . C14 C 0.1684(15) 0.0531(15) 0.894(2) 0.178(10) Uani 1 1 d DU . . H14A H 0.1498 0.0405 0.9656 0.214 Uiso 1 1 calc R . . H14B H 0.1594 0.0073 0.8412 0.214 Uiso 1 1 calc R . . H14C H 0.1428 0.1008 0.8582 0.214 Uiso 1 1 calc R . . O3 O -0.0312(3) 0.0175(3) 0.9079(5) 0.0400(14) Uani 1 1 d . . . H3WA H 0.0101 -0.0161 0.8923 0.048 Uiso 1 1 d R . . H3WB H -0.0598 0.0270 0.8458 0.048 Uiso 1 1 d 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 Si1 0.0206(8) 0.0403(11) 0.0169(9) -0.0001(8) -0.0003(7) 0.0091(7) Cu1 0.0169(5) 0.0262(6) 0.0165(6) 0.000 -0.0017(4) 0.000 Br1 0.0255(5) 0.0227(5) 0.0329(6) 0.000 0.0042(4) 0.000 Br2 0.254(5) 0.109(3) 0.189(4) 0.000 -0.040(3) 0.000 O1 0.26(3) 0.27(3) 0.24(2) 0.036(19) 0.06(2) 0.10(2) O2 0.125(7) 0.009(3) 0.071(5) -0.005(3) -0.045(5) 0.006(3) N1 0.018(2) 0.034(3) 0.016(2) 0.000(2) 0.0008(19) 0.001(2) N2 0.020(2) 0.033(3) 0.019(3) 0.000(2) 0.000(2) 0.003(2) C1 0.022(3) 0.032(4) 0.031(4) -0.005(3) 0.002(3) 0.005(3) C2 0.023(3) 0.034(4) 0.031(4) -0.004(3) 0.002(3) 0.000(3) C3 0.023(3) 0.038(4) 0.016(3) 0.001(3) -0.003(2) 0.008(3) C4 0.026(3) 0.037(4) 0.024(3) -0.003(3) 0.001(3) 0.006(3) C5 0.027(3) 0.028(4) 0.033(4) -0.005(3) 0.002(3) -0.002(3) C6 0.037(4) 0.034(4) 0.023(3) 0.000(3) 0.002(3) 0.015(3) C7 0.038(4) 0.044(4) 0.020(3) -0.007(3) -0.002(3) 0.013(3) C8 0.018(3) 0.035(4) 0.019(3) 0.002(3) 0.001(2) 0.006(2) C9 0.042(4) 0.027(4) 0.029(4) 0.002(3) -0.004(3) 0.006(3) C10 0.043(4) 0.027(4) 0.025(3) -0.002(3) -0.005(3) 0.005(3) C11 0.035(4) 0.057(5) 0.023(3) -0.003(3) 0.001(3) 0.017(3) C12 0.035(4) 0.060(5) 0.028(4) 0.009(4) 0.007(3) 0.006(4) C13 0.200(18) 0.140(15) 0.182(17) 0.025(13) 0.031(15) 0.002(14) C14 0.157(16) 0.163(16) 0.213(19) -0.015(14) 0.026(15) -0.018(14) O3 0.057(3) 0.018(2) 0.043(3) -0.013(2) 0.005(3) 0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 C12 1.852(9) . ? Si1 C11 1.866(8) . ? Si1 C8 1.890(6) . ? Si1 C3 1.897(7) . ? Cu1 N2 2.043(5) 8_455 ? Cu1 N2 2.043(5) 7_557 ? Cu1 N1 2.045(5) . ? Cu1 N1 2.045(5) 2_556 ? Cu1 Br1 2.5870(14) . ? Br2 O3 2.143(6) 2_556 ? Br2 O3 2.143(6) . ? Br2 H3WB 1.7750 . ? O1 C14 1.45(3) . ? O1 H1M 0.8400 . ? O2 C13 1.412(16) . ? O2 H2 0.8400 . ? N1 C5 1.323(9) . ? N1 C1 1.346(8) . ? N2 C6 1.333(9) . ? N2 C10 1.344(9) . ? N2 Cu1 2.043(5) 7_557 ? C1 C2 1.375(9) . ? C1 H1A 0.9500 . ? C2 C3 1.383(10) . ? C2 H2A 0.9500 . ? C3 C4 1.385(10) . ? C4 C5 1.399(9) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.392(9) . ? C6 H6A 0.9500 . ? C7 C8 1.366(10) . ? C7 H7A 0.9500 . ? C8 C9 1.394(10) . ? C9 C10 1.376(9) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O3 H3WA 0.9800 . ? O3 H3WB 0.8399 . ? 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 C12 Si1 C11 114.6(4) . . ? C12 Si1 C8 108.6(3) . . ? C11 Si1 C8 109.1(3) . . ? C12 Si1 C3 109.4(3) . . ? C11 Si1 C3 109.6(3) . . ? C8 Si1 C3 105.0(3) . . ? N2 Cu1 N2 160.5(3) 8_455 7_557 ? N2 Cu1 N1 89.3(2) 8_455 . ? N2 Cu1 N1 87.9(2) 7_557 . ? N2 Cu1 N1 87.9(2) 8_455 2_556 ? N2 Cu1 N1 89.3(2) 7_557 2_556 ? N1 Cu1 N1 163.3(3) . 2_556 ? N2 Cu1 Br1 99.76(16) 8_455 . ? N2 Cu1 Br1 99.76(16) 7_557 . ? N1 Cu1 Br1 98.36(16) . . ? N1 Cu1 Br1 98.36(16) 2_556 . ? O3 Br2 O3 142.7(3) 2_556 . ? O3 Br2 H3WB 137.4 2_556 . ? O3 Br2 H3WB 22.3 . . ? C14 O1 H1M 109.5 . . ? C13 O2 H2 109.5 . . ? C5 N1 C1 117.7(6) . . ? C5 N1 Cu1 120.3(5) . . ? C1 N1 Cu1 121.4(4) . . ? C6 N2 C10 118.6(6) . . ? C6 N2 Cu1 120.6(4) . 7_557 ? C10 N2 Cu1 120.7(5) . 7_557 ? N1 C1 C2 122.9(6) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C1 C2 C3 120.1(6) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 116.9(6) . . ? C2 C3 Si1 121.8(5) . . ? C4 C3 Si1 121.3(5) . . ? C3 C4 C5 120.0(6) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N1 C5 C4 122.3(6) . . ? N1 C5 H5A 118.8 . . ? C4 C5 H5A 118.8 . . ? N2 C6 C7 120.9(6) . . ? N2 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C8 C7 C6 122.4(7) . . ? C8 C7 H7A 118.8 . . ? C6 C7 H7A 118.8 . . ? C7 C8 C9 115.1(6) . . ? C7 C8 Si1 123.1(5) . . ? C9 C8 Si1 121.8(5) . . ? C10 C9 C8 121.5(6) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? N2 C10 C9 121.6(6) . . ? N2 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Br2 O3 H3WA 72.3 . . ? Br2 O3 H3WB 53.4 . . ? H3WA O3 H3WB 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.055 _refine_diff_density_min -3.876 _refine_diff_density_rms 0.237 _vrf_PLAT413_ss ; PROBLEM: Short Inter XH3 .. XHn H11C .. H13C .. 1.76 Ang. RESPONSE: The hydrogen atoms were placed in calculated positions (C-H 0.98 Ang., O-H 0.84 Ang.) and refined using a riding model. The short distances between the hydrogen atoms of the methanol solvated molecules may come from the close location between the methanol molecules, and thus, are unavoidable. ; _vrf_PLAT415_ss ; PROBLEM: Short Inter D-H..H-X H1M .. H13A .. 1.76 Ang. RESPONSE: The hydrogen atoms were placed in calculated positions (C-H 0.98 Ang., O-H 0.84 Ang.) and refined using a riding model. The short distances between the hydrogen atoms of the methanol solvated molecules may come from the close location between the methanol molecules, and thus, are unavoidable. ; data_nth _database_code_depnum_ccdc_archive 'CCDC 923407' #TrackingRef '923407.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H40 Br2 Cu N4 O2 S2 Si2' _chemical_formula_weight 808.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 12.1935(2) _cell_length_b 20.2551(3) _cell_length_c 15.1134(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.9440(10) _cell_angle_gamma 90.00 _cell_volume 3696.90(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4526 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 27.02 _exptl_crystal_description BLOCK _exptl_crystal_colour blue _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1644 _exptl_absorpt_coefficient_mu 2.960 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3626 _exptl_absorpt_correction_T_max 0.5021 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Breeze CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31030 _diffrn_reflns_av_R_equivalents 0.1251 _diffrn_reflns_av_sigmaI/netI 0.0957 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7239 _reflns_number_gt 4627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0210P)^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_extinction_coef ? _refine_ls_number_reflns 7239 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.31964(4) 0.12425(3) 0.28968(3) 0.02098(13) Uani 1 1 d . . . Br1 Br 0.51937(3) 0.11800(3) 0.39061(3) 0.02861(13) Uani 1 1 d . . . Si1 Si 0.10740(9) 0.37860(6) 0.49862(7) 0.0212(3) Uani 1 1 d . . . S1 S 0.85889(14) 0.33840(9) 0.18056(11) 0.0657(5) Uani 1 1 d . . . O1 O 0.8780(3) 0.3367(2) 0.2816(2) 0.0505(10) Uani 1 1 d . . . N1 N 0.2535(3) 0.19597(17) 0.3607(2) 0.0204(8) Uani 1 1 d . . . C1 C 0.1479(3) 0.2150(2) 0.3393(3) 0.0247(10) Uani 1 1 d . . . H1A H 0.1031 0.1919 0.2950 0.030 Uiso 1 1 calc R . . Br2 Br 0.00598(3) 0.13259(3) 0.12560(3) 0.03256(14) Uani 1 1 d . . . Si2 Si 0.42706(9) 0.37397(6) 0.02125(7) 0.0235(3) Uani 1 1 d . . . S2 S 0.65061(12) 0.41328(8) 0.35404(9) 0.0505(4) Uani 1 1 d . . . O2 O 0.6307(3) 0.4112(2) 0.2540(2) 0.0549(10) Uani 1 1 d . . . N2 N 0.1544(3) 0.55498(17) 0.3036(2) 0.0211(8) Uani 1 1 d . . . C2 C 0.1028(3) 0.2673(2) 0.3800(3) 0.0245(10) Uani 1 1 d . . . H2A H 0.0291 0.2785 0.3624 0.029 Uiso 1 1 calc R . . N3 N 0.3561(3) 0.19696(17) 0.2068(2) 0.0213(8) Uani 1 1 d . . . C3 C 0.1649(3) 0.3037(2) 0.4466(3) 0.0200(10) Uani 1 1 d . . . N4 N 0.2570(3) 0.55207(17) 0.1487(2) 0.0210(8) Uani 1 1 d . . . C4 C 0.2747(4) 0.2838(2) 0.4680(3) 0.0299(11) Uani 1 1 d . . . H4A H 0.3213 0.3064 0.5118 0.036 Uiso 1 1 calc R . . C5 C 0.3148(3) 0.2310(2) 0.4249(3) 0.0300(11) Uani 1 1 d . . . H5A H 0.3884 0.2190 0.4411 0.036 Uiso 1 1 calc R . . C6 C -0.0431(3) 0.3676(2) 0.4992(3) 0.0272(10) Uani 1 1 d . . . H6A H -0.0554 0.3314 0.5376 0.033 Uiso 1 1 calc R . . H6B H -0.0782 0.3585 0.4397 0.033 Uiso 1 1 calc R . . H6C H -0.0737 0.4072 0.5207 0.033 Uiso 1 1 calc R . . C7 C 0.1846(4) 0.3945(2) 0.6108(3) 0.0338(12) Uani 1 1 d . . . H7A H 0.1744 0.3582 0.6496 0.041 Uiso 1 1 calc R . . H7B H 0.1575 0.4343 0.6347 0.041 Uiso 1 1 calc R . . H7C H 0.2619 0.3994 0.6063 0.041 Uiso 1 1 calc R . . C8 C 0.1282(3) 0.4501(2) 0.4228(3) 0.0206(10) Uani 1 1 d . . . C9 C 0.2272(4) 0.4848(2) 0.4254(3) 0.0283(11) Uani 1 1 d . . . H9A H 0.2871 0.4735 0.4677 0.034 Uiso 1 1 calc R . . C10 C 0.2384(4) 0.5356(2) 0.3667(3) 0.0284(11) Uani 1 1 d . . . H10A H 0.3060 0.5574 0.3704 0.034 Uiso 1 1 calc R . . C11 C 0.0596(4) 0.5231(2) 0.3011(3) 0.0288(11) Uani 1 1 d . . . H11A H 0.0009 0.5358 0.2586 0.035 Uiso 1 1 calc R . . C12 C 0.0425(3) 0.4722(2) 0.3575(3) 0.0282(11) Uani 1 1 d . . . H12A H -0.0266 0.4521 0.3526 0.034 Uiso 1 1 calc R . . C13 C 0.2764(4) 0.2213(2) 0.1440(3) 0.0283(11) Uani 1 1 d . . . H13A H 0.2063 0.2024 0.1387 0.034 Uiso 1 1 calc R . . C14 C 0.2937(4) 0.2721(2) 0.0881(3) 0.0295(11) Uani 1 1 d . . . H14A H 0.2360 0.2867 0.0459 0.035 Uiso 1 1 calc R . . C15 C 0.3973(4) 0.3024(2) 0.0938(3) 0.0229(10) Uani 1 1 d . . . C16 C 0.4774(4) 0.2777(2) 0.1589(3) 0.0294(11) Uani 1 1 d . . . H16A H 0.5479 0.2962 0.1668 0.035 Uiso 1 1 calc R . . C17 C 0.4539(4) 0.2257(2) 0.2123(3) 0.0313(11) Uani 1 1 d . . . H17A H 0.5104 0.2101 0.2548 0.038 Uiso 1 1 calc R . . C18 C 0.3607(4) 0.3602(2) -0.0955(3) 0.0332(12) Uani 1 1 d . . . H18A H 0.3948 0.3231 -0.1203 0.040 Uiso 1 1 calc R . . H18B H 0.3697 0.3988 -0.1305 0.040 Uiso 1 1 calc R . . H18C H 0.2832 0.3515 -0.0959 0.040 Uiso 1 1 calc R . . C19 C 0.5795(3) 0.3850(2) 0.0322(3) 0.0298(11) Uani 1 1 d . . . H19A H 0.6121 0.3476 0.0068 0.036 Uiso 1 1 calc R . . H19B H 0.6091 0.3888 0.0943 0.036 Uiso 1 1 calc R . . H19C H 0.5962 0.4244 0.0013 0.036 Uiso 1 1 calc R . . C20 C 0.3611(4) 0.4469(2) 0.0709(3) 0.0220(10) Uani 1 1 d . . . C21 C 0.4159(4) 0.4844(2) 0.1403(3) 0.0246(10) Uani 1 1 d . . . H21A H 0.4890 0.4747 0.1626 0.030 Uiso 1 1 calc R . . C22 C 0.3631(4) 0.5357(2) 0.1764(3) 0.0254(11) Uani 1 1 d . . . H22A H 0.4026 0.5602 0.2221 0.030 Uiso 1 1 calc R . . C23 C 0.2030(4) 0.5154(2) 0.0832(3) 0.0293(11) Uani 1 1 d . . . H23A H 0.1290 0.5250 0.0639 0.035 Uiso 1 1 calc R . . C24 C 0.2510(4) 0.4638(2) 0.0424(3) 0.0312(11) Uani 1 1 d . . . H24A H 0.2100 0.4405 -0.0038 0.037 Uiso 1 1 calc R . . C25 C 0.9918(6) 0.3232(4) 0.1466(4) 0.092(3) Uani 1 1 d . . . H25A H 1.0120 0.2778 0.1580 0.110 Uiso 1 1 calc R . . H25B H 1.0460 0.3513 0.1798 0.110 Uiso 1 1 calc R . . H25C H 0.9885 0.3322 0.0840 0.110 Uiso 1 1 calc R . . C26 C 0.8555(5) 0.4217(3) 0.1480(4) 0.073(2) Uani 1 1 d . . . H26A H 0.7877 0.4414 0.1605 0.088 Uiso 1 1 calc R . . H26B H 0.8596 0.4246 0.0852 0.088 Uiso 1 1 calc R . . H26C H 0.9172 0.4445 0.1806 0.088 Uiso 1 1 calc R . . C27 C 0.5252(5) 0.4383(3) 0.3877(3) 0.0671(19) Uani 1 1 d . . . H27A H 0.5122 0.4840 0.3728 0.081 Uiso 1 1 calc R . . H27B H 0.5288 0.4326 0.4511 0.081 Uiso 1 1 calc R . . H27C H 0.4658 0.4121 0.3577 0.081 Uiso 1 1 calc R . . C28 C 0.6466(5) 0.3307(3) 0.3910(4) 0.0666(18) Uani 1 1 d . . . H28A H 0.7110 0.3077 0.3774 0.080 Uiso 1 1 calc R . . H28B H 0.5813 0.3095 0.3614 0.080 Uiso 1 1 calc R . . H28C H 0.6454 0.3301 0.4544 0.080 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 0.0234(3) 0.0161(3) 0.0244(3) -0.0002(2) 0.0071(2) 0.0011(2) Br1 0.0221(2) 0.0302(3) 0.0322(2) 0.0007(2) -0.00124(17) 0.0033(2) Si1 0.0221(5) 0.0191(7) 0.0233(6) 0.0002(6) 0.0062(5) 0.0005(5) S1 0.0664(11) 0.0613(12) 0.0635(10) 0.0045(9) -0.0122(8) -0.0028(9) O1 0.048(2) 0.067(3) 0.0344(19) 0.0087(19) -0.0016(16) 0.016(2) N1 0.0217(18) 0.018(2) 0.0221(19) 0.0006(16) 0.0030(15) 0.0003(16) C1 0.025(2) 0.024(3) 0.025(2) -0.003(2) 0.0024(19) -0.001(2) Br2 0.0239(2) 0.0361(3) 0.0358(3) 0.0038(2) -0.00246(18) 0.0030(2) Si2 0.0269(6) 0.0195(7) 0.0248(6) -0.0009(6) 0.0060(5) -0.0002(6) S2 0.0579(9) 0.0506(10) 0.0388(8) 0.0020(7) -0.0086(7) 0.0046(8) O2 0.053(2) 0.078(3) 0.0325(19) 0.004(2) 0.0024(16) 0.018(2) N2 0.0234(18) 0.015(2) 0.0265(19) -0.0036(16) 0.0089(16) -0.0013(16) C2 0.018(2) 0.026(3) 0.029(2) -0.001(2) 0.0008(18) 0.004(2) N3 0.0202(18) 0.023(2) 0.0216(19) -0.0025(16) 0.0060(15) 0.0004(16) C3 0.020(2) 0.019(3) 0.022(2) 0.0022(19) 0.0049(17) -0.0014(19) N4 0.0264(19) 0.016(2) 0.0209(19) 0.0023(16) 0.0049(15) 0.0000(16) C4 0.025(2) 0.032(3) 0.031(3) -0.010(2) -0.0053(19) -0.001(2) C5 0.021(2) 0.032(3) 0.037(3) -0.007(2) 0.003(2) 0.009(2) C6 0.029(2) 0.024(3) 0.031(2) 0.008(2) 0.0116(19) 0.001(2) C7 0.034(2) 0.043(4) 0.026(2) -0.005(2) 0.010(2) 0.006(2) C8 0.026(2) 0.015(3) 0.023(2) -0.0021(19) 0.0107(19) 0.0006(19) C9 0.025(2) 0.030(3) 0.029(2) 0.003(2) 0.000(2) -0.001(2) C10 0.022(2) 0.029(3) 0.035(3) -0.002(2) 0.006(2) -0.009(2) C11 0.026(2) 0.028(3) 0.031(3) 0.006(2) 0.001(2) 0.001(2) C12 0.022(2) 0.029(3) 0.034(3) 0.001(2) 0.006(2) -0.009(2) C13 0.023(2) 0.030(3) 0.033(3) -0.002(2) 0.006(2) -0.003(2) C14 0.026(2) 0.026(3) 0.036(3) 0.006(2) 0.002(2) 0.005(2) C15 0.028(2) 0.019(3) 0.023(2) -0.004(2) 0.0081(19) 0.000(2) C16 0.024(2) 0.029(3) 0.035(3) 0.001(2) 0.001(2) -0.011(2) C17 0.034(3) 0.031(3) 0.027(2) 0.004(2) -0.001(2) -0.003(2) C18 0.035(3) 0.040(4) 0.025(2) -0.005(2) 0.004(2) 0.010(2) C19 0.031(2) 0.031(3) 0.030(2) 0.003(2) 0.011(2) -0.001(2) C20 0.028(2) 0.016(3) 0.022(2) 0.0045(19) 0.0068(19) -0.001(2) C21 0.025(2) 0.023(3) 0.024(2) -0.002(2) -0.0021(19) 0.005(2) C22 0.029(2) 0.025(3) 0.022(2) 0.002(2) 0.0028(19) 0.000(2) C23 0.021(2) 0.028(3) 0.038(3) -0.007(2) 0.001(2) 0.001(2) C24 0.032(3) 0.027(3) 0.034(3) -0.006(2) 0.002(2) -0.002(2) C25 0.128(7) 0.105(7) 0.047(4) 0.008(4) 0.026(4) 0.031(5) C26 0.076(5) 0.059(5) 0.079(4) 0.020(4) -0.010(4) -0.011(4) C27 0.091(5) 0.063(5) 0.048(3) 0.012(3) 0.012(3) 0.031(4) C28 0.075(4) 0.052(4) 0.067(4) 0.004(3) -0.012(3) 0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.023(3) . ? Cu1 N4 2.029(3) 2_545 ? Cu1 N1 2.038(3) . ? Cu1 N2 2.044(3) 2_545 ? Cu1 Br1 2.6921(6) . ? Si1 C6 1.849(4) . ? Si1 C7 1.850(4) . ? Si1 C8 1.885(4) . ? Si1 C3 1.888(4) . ? S1 O1 1.514(3) . ? S1 C26 1.755(6) . ? S1 C25 1.793(7) . ? N1 C1 1.340(5) . ? N1 C5 1.343(5) . ? C1 C2 1.378(6) . ? C1 H1A 0.9300 . ? Si2 C19 1.857(4) . ? Si2 C18 1.858(4) . ? Si2 C15 1.883(4) . ? Si2 C20 1.887(4) . ? S2 O2 1.498(3) . ? S2 C27 1.752(6) . ? S2 C28 1.766(6) . ? N2 C11 1.321(5) . ? N2 C10 1.357(5) . ? N2 Cu1 2.044(3) 2 ? C2 C3 1.384(6) . ? C2 H2A 0.9300 . ? N3 C17 1.319(5) . ? N3 C13 1.353(5) . ? C3 C4 1.393(5) . ? N4 C23 1.337(5) . ? N4 C22 1.346(5) . ? N4 Cu1 2.029(3) 2 ? C4 C5 1.377(6) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.394(6) . ? C8 C12 1.407(6) . ? C9 C10 1.377(6) . ? C9 H9A 0.9300 . ? C10 H10A 0.9300 . ? C11 C12 1.370(6) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.368(6) . ? C13 H13A 0.9300 . ? C14 C15 1.396(6) . ? C14 H14A 0.9300 . ? C15 C16 1.381(6) . ? C16 C17 1.381(6) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.389(6) . ? C20 C24 1.395(6) . ? C21 C22 1.374(6) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.382(6) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N4 164.47(14) . 2_545 ? N3 Cu1 N1 86.80(13) . . ? N4 Cu1 N1 91.79(12) 2_545 . ? N3 Cu1 N2 90.24(12) . 2_545 ? N4 Cu1 N2 86.95(13) 2_545 2_545 ? N1 Cu1 N2 164.31(14) . 2_545 ? N3 Cu1 Br1 97.24(10) . . ? N4 Cu1 Br1 98.28(10) 2_545 . ? N1 Cu1 Br1 97.35(10) . . ? N2 Cu1 Br1 98.31(10) 2_545 . ? C6 Si1 C7 113.33(19) . . ? C6 Si1 C8 108.21(19) . . ? C7 Si1 C8 109.2(2) . . ? C6 Si1 C3 109.3(2) . . ? C7 Si1 C3 110.52(19) . . ? C8 Si1 C3 106.00(17) . . ? O1 S1 C26 107.4(3) . . ? O1 S1 C25 105.4(2) . . ? C26 S1 C25 94.2(3) . . ? C1 N1 C5 116.2(4) . . ? C1 N1 Cu1 121.0(3) . . ? C5 N1 Cu1 122.4(3) . . ? N1 C1 C2 122.9(4) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C19 Si2 C18 113.74(19) . . ? C19 Si2 C15 108.2(2) . . ? C18 Si2 C15 110.1(2) . . ? C19 Si2 C20 110.3(2) . . ? C18 Si2 C20 110.0(2) . . ? C15 Si2 C20 104.13(17) . . ? O2 S2 C27 105.9(2) . . ? O2 S2 C28 106.5(3) . . ? C27 S2 C28 96.8(3) . . ? C11 N2 C10 116.8(4) . . ? C11 N2 Cu1 122.3(3) . 2 ? C10 N2 Cu1 120.6(3) . 2 ? C1 C2 C3 121.5(4) . . ? C1 C2 H2A 119.3 . . ? C3 C2 H2A 119.3 . . ? C17 N3 C13 116.1(4) . . ? C17 N3 Cu1 123.8(3) . . ? C13 N3 Cu1 120.0(3) . . ? C2 C3 C4 115.2(4) . . ? C2 C3 Si1 122.2(3) . . ? C4 C3 Si1 122.4(3) . . ? C23 N4 C22 116.5(4) . . ? C23 N4 Cu1 122.0(3) . 2 ? C22 N4 Cu1 121.3(3) . 2 ? C5 C4 C3 120.5(4) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? N1 C5 C4 123.7(4) . . ? N1 C5 H5A 118.2 . . ? C4 C5 H5A 118.2 . . ? Si1 C6 H6A 109.5 . . ? Si1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? Si1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C12 114.5(4) . . ? C9 C8 Si1 124.0(3) . . ? C12 C8 Si1 121.5(3) . . ? C10 C9 C8 121.4(4) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? N2 C10 C9 122.5(4) . . ? N2 C10 H10A 118.8 . . ? C9 C10 H10A 118.8 . . ? N2 C11 C12 123.9(4) . . ? N2 C11 H11A 118.1 . . ? C12 C11 H11A 118.1 . . ? C11 C12 C8 120.9(4) . . ? C11 C12 H12A 119.5 . . ? C8 C12 H12A 119.5 . . ? N3 C13 C14 123.3(4) . . ? N3 C13 H13A 118.3 . . ? C14 C13 H13A 118.3 . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C16 C15 C14 115.5(4) . . ? C16 C15 Si2 121.3(3) . . ? C14 C15 Si2 123.2(3) . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? N3 C17 C16 123.9(4) . . ? N3 C17 H17A 118.0 . . ? C16 C17 H17A 118.0 . . ? Si2 C18 H18A 109.5 . . ? Si2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Si2 C19 H19A 109.5 . . ? Si2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Si2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C24 116.2(4) . . ? C21 C20 Si2 122.8(3) . . ? C24 C20 Si2 121.0(3) . . ? C22 C21 C20 120.7(4) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 119.7 . . ? N4 C22 C21 123.1(4) . . ? N4 C22 H22A 118.4 . . ? C21 C22 H22A 118.4 . . ? N4 C23 C24 123.7(4) . . ? N4 C23 H23A 118.2 . . ? C24 C23 H23A 118.2 . . ? C23 C24 C20 119.8(4) . . ? C23 C24 H24A 120.1 . . ? C20 C24 H24A 120.1 . . ? S1 C25 H25A 109.5 . . ? S1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? S1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? S1 C26 H26A 109.5 . . ? S1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? S1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? S2 C27 H27A 109.5 . . ? S2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? S2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? S2 C28 H28A 109.5 . . ? S2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? S2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.756 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.109 data_aa2 _database_code_depnum_ccdc_archive 'CCDC 923408' #TrackingRef '03-M.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H26 Br2 Cu N2 O2 S2 Si' _chemical_formula_weight 593.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+3/4' 'y, -x, z+1/4' _cell_length_a 11.96630(10) _cell_length_b 11.96630(10) _cell_length_c 16.2923(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2332.93(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2065 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 4.605 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3035 _exptl_absorpt_correction_T_max 0.3694 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Breeze CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6602 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3677 _reflns_number_gt 2996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0287P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.006(10) _refine_ls_number_reflns 3677 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0709 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.04446(6) 0.33749(6) 0.23362(4) 0.02338(17) Uani 1 1 d . . . Si1 Si 0.17129(13) 0.84920(13) 0.08637(10) 0.0207(4) Uani 1 1 d . . . Br1 Br -0.01078(8) 0.39901(6) 0.36961(5) 0.0550(3) Uani 1 1 d . . . Br2 Br 0.20393(5) 0.26184(5) 0.15753(4) 0.03259(16) Uani 1 1 d . . . S1 S -0.18456(16) 0.43431(14) 0.14030(12) 0.0453(5) Uani 1 1 d . . . S2 S 0.44323(18) 0.62121(17) 0.11495(16) 0.0591(6) Uani 1 1 d . . . O1 O -0.0938(3) 0.3465(3) 0.1432(3) 0.0332(11) Uani 1 1 d . . . O2 O 0.5493(5) 0.5859(5) 0.0757(4) 0.0748(19) Uani 1 1 d . . . N1 N 0.0876(4) 0.4948(4) 0.1968(3) 0.0235(11) Uani 1 1 d . . . N2 N -0.1822(4) 0.9932(4) 0.0153(3) 0.0283(12) Uani 1 1 d . . . C1 C 0.0931(5) 0.5133(5) 0.1165(4) 0.0266(14) Uani 1 1 d . . . H1A H 0.0793 0.4523 0.0806 0.032 Uiso 1 1 calc R . . C2 C 0.1177(5) 0.6158(4) 0.0820(3) 0.0208(13) Uani 1 1 d . . . H2A H 0.1173 0.6242 0.0241 0.025 Uiso 1 1 calc R . . C3 C 0.1428(4) 0.7066(4) 0.1314(4) 0.0186(12) Uani 1 1 d . . . C4 C 0.1388(4) 0.6857(5) 0.2160(3) 0.0203(13) Uani 1 1 d . . . H4A H 0.1546 0.7447 0.2533 0.024 Uiso 1 1 calc R . . C5 C 0.1123(5) 0.5815(5) 0.2465(4) 0.0250(13) Uani 1 1 d . . . H5A H 0.1114 0.5705 0.3042 0.030 Uiso 1 1 calc R . . C6 C 0.2449(5) 0.8294(5) -0.0131(4) 0.0345(15) Uani 1 1 d . . . H6A H 0.2602 0.9025 -0.0379 0.052 Uiso 1 1 calc R . . H6B H 0.1978 0.7853 -0.0502 0.052 Uiso 1 1 calc R . . H6C H 0.3155 0.7900 -0.0037 0.052 Uiso 1 1 calc R . . C7 C 0.2517(5) 0.9371(5) 0.1596(4) 0.0311(15) Uani 1 1 d . . . H7A H 0.2655 1.0106 0.1351 0.047 Uiso 1 1 calc R . . H7B H 0.3232 0.9008 0.1720 0.047 Uiso 1 1 calc R . . H7C H 0.2087 0.9462 0.2104 0.047 Uiso 1 1 calc R . . C8 C 0.0289(5) 0.9102(5) 0.0637(4) 0.0220(13) Uani 1 1 d . . . C9 C -0.0537(5) 0.8425(5) 0.0278(4) 0.0349(17) Uani 1 1 d . . . H9A H -0.0391 0.7654 0.0187 0.042 Uiso 1 1 calc R . . C10 C -0.1543(5) 0.8861(5) 0.0059(4) 0.0371(17) Uani 1 1 d . . . H10A H -0.2081 0.8372 -0.0176 0.045 Uiso 1 1 calc R . . C11 C -0.1053(5) 1.0601(5) 0.0489(4) 0.0285(15) Uani 1 1 d . . . H11A H -0.1221 1.1372 0.0556 0.034 Uiso 1 1 calc R . . C12 C -0.0031(5) 1.0215(5) 0.0741(4) 0.0261(14) Uani 1 1 d . . . H12A H 0.0475 1.0720 0.0994 0.031 Uiso 1 1 calc R . . C13 C -0.3113(6) 0.3562(7) 0.1400(6) 0.070(3) Uani 1 1 d . . . H13A H -0.3252 0.3264 0.1951 0.105 Uiso 1 1 calc R . . H13B H -0.3050 0.2944 0.1009 0.105 Uiso 1 1 calc R . . H13C H -0.3733 0.4050 0.1239 0.105 Uiso 1 1 calc R . . C14 C -0.1936(7) 0.4764(8) 0.0371(5) 0.071(3) Uani 1 1 d . . . H14A H -0.1270 0.5198 0.0226 0.107 Uiso 1 1 calc R . . H14B H -0.2604 0.5227 0.0295 0.107 Uiso 1 1 calc R . . H14C H -0.1984 0.4103 0.0018 0.107 Uiso 1 1 calc R . . C15 C 0.4802(8) 0.7127(7) 0.1937(5) 0.065(3) Uani 1 1 d . . . H15A H 0.5065 0.7833 0.1701 0.098 Uiso 1 1 calc R . . H15B H 0.5400 0.6793 0.2268 0.098 Uiso 1 1 calc R . . H15C H 0.4150 0.7270 0.2286 0.098 Uiso 1 1 calc R . . C16 C 0.3992(6) 0.5051(7) 0.1757(6) 0.065(3) Uani 1 1 d . . . H16A H 0.3759 0.4439 0.1395 0.097 Uiso 1 1 calc R . . H16B H 0.3363 0.5275 0.2105 0.097 Uiso 1 1 calc R . . H16C H 0.4613 0.4800 0.2103 0.097 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 0.0276(4) 0.0174(3) 0.0251(4) 0.0022(3) 0.0029(4) -0.0029(3) Si1 0.0187(8) 0.0168(7) 0.0267(9) 0.0041(7) -0.0008(7) 0.0003(7) Br1 0.0950(7) 0.0316(4) 0.0385(4) -0.0032(4) 0.0347(5) -0.0130(4) Br2 0.0373(4) 0.0224(3) 0.0380(4) -0.0024(3) 0.0127(3) -0.0012(3) S1 0.0556(11) 0.0290(8) 0.0513(12) 0.0006(9) -0.0146(11) 0.0058(9) S2 0.0556(12) 0.0487(11) 0.0729(15) -0.0061(12) -0.0218(13) 0.0063(11) O1 0.034(2) 0.025(2) 0.041(3) 0.008(2) -0.010(2) -0.003(2) O2 0.071(4) 0.070(4) 0.084(5) -0.007(4) 0.019(4) 0.021(3) N1 0.024(3) 0.022(3) 0.025(3) 0.003(2) 0.008(2) 0.004(2) N2 0.023(3) 0.027(3) 0.035(3) 0.007(3) -0.005(2) -0.001(2) C1 0.026(3) 0.026(3) 0.028(3) -0.007(3) -0.006(3) 0.003(3) C2 0.026(3) 0.020(3) 0.017(3) 0.002(3) 0.001(3) -0.005(3) C3 0.014(2) 0.017(3) 0.025(3) 0.002(2) 0.004(2) 0.005(2) C4 0.020(3) 0.021(3) 0.020(3) -0.001(3) 0.001(3) -0.003(3) C5 0.031(3) 0.020(3) 0.024(3) 0.000(3) 0.002(3) -0.004(3) C6 0.037(4) 0.028(3) 0.038(4) 0.003(3) 0.011(4) 0.000(3) C7 0.030(3) 0.020(3) 0.043(4) -0.001(3) -0.006(3) -0.008(3) C8 0.022(3) 0.021(3) 0.023(3) 0.000(3) -0.002(3) -0.004(3) C9 0.035(4) 0.018(3) 0.051(5) -0.001(3) -0.016(4) 0.008(3) C10 0.029(3) 0.028(3) 0.054(5) 0.001(3) -0.016(3) -0.003(3) C11 0.025(3) 0.026(3) 0.034(4) -0.003(3) -0.004(3) 0.010(3) C12 0.023(3) 0.020(3) 0.036(4) -0.002(3) -0.007(3) -0.001(3) C13 0.041(4) 0.079(6) 0.090(7) 0.034(6) 0.014(5) 0.016(4) C14 0.051(5) 0.089(7) 0.073(6) 0.050(6) -0.011(5) -0.001(5) C15 0.077(6) 0.051(5) 0.068(6) 0.004(5) -0.013(5) -0.018(5) C16 0.041(4) 0.055(5) 0.099(7) 0.011(5) -0.007(5) -0.005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.024(5) 4_455 ? Cu1 N1 2.042(5) . ? Cu1 O1 2.218(4) . ? Cu1 Br1 2.4265(10) . ? Cu1 Br2 2.4491(9) . ? Si1 C7 1.859(6) . ? Si1 C6 1.860(7) . ? Si1 C3 1.888(5) . ? Si1 C8 1.890(6) . ? S1 O1 1.512(4) . ? S1 C14 1.758(8) . ? S1 C13 1.781(8) . ? S2 O2 1.483(6) . ? S2 C15 1.745(8) . ? S2 C16 1.785(8) . ? N1 C1 1.329(8) . ? N1 C5 1.348(7) . ? N2 C10 1.333(7) . ? N2 C11 1.337(7) . ? N2 Cu1 2.024(5) 3_564 ? C1 C2 1.380(8) . ? C2 C3 1.385(8) . ? C3 C4 1.402(8) . ? C4 C5 1.378(7) . ? C8 C12 1.396(8) . ? C8 C9 1.406(8) . ? C9 C10 1.360(8) . ? C11 C12 1.370(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 176.4(2) 4_455 . ? N2 Cu1 O1 89.32(18) 4_455 . ? N1 Cu1 O1 87.09(17) . . ? N2 Cu1 Br1 87.88(15) 4_455 . ? N1 Cu1 Br1 93.28(14) . . ? O1 Cu1 Br1 112.87(12) . . ? N2 Cu1 Br2 91.48(14) 4_455 . ? N1 Cu1 Br2 89.72(13) . . ? O1 Cu1 Br2 105.24(12) . . ? Br1 Cu1 Br2 141.87(4) . . ? C7 Si1 C6 112.7(3) . . ? C7 Si1 C3 110.8(3) . . ? C6 Si1 C3 108.0(3) . . ? C7 Si1 C8 111.9(3) . . ? C6 Si1 C8 107.8(3) . . ? C3 Si1 C8 105.2(2) . . ? O1 S1 C14 105.8(4) . . ? O1 S1 C13 104.3(3) . . ? C14 S1 C13 95.5(4) . . ? O2 S2 C15 106.2(4) . . ? O2 S2 C16 105.7(4) . . ? C15 S2 C16 99.0(4) . . ? S1 O1 Cu1 126.1(3) . . ? C1 N1 C5 116.9(5) . . ? C1 N1 Cu1 117.1(4) . . ? C5 N1 Cu1 126.1(4) . . ? C10 N2 C11 116.8(5) . . ? C10 N2 Cu1 119.4(4) . 3_564 ? C11 N2 Cu1 123.7(4) . 3_564 ? N1 C1 C2 124.0(6) . . ? C1 C2 C3 120.5(5) . . ? C2 C3 C4 115.1(5) . . ? C2 C3 Si1 121.5(4) . . ? C4 C3 Si1 123.4(4) . . ? C5 C4 C3 121.5(5) . . ? N1 C5 C4 122.1(5) . . ? C12 C8 C9 114.0(5) . . ? C12 C8 Si1 126.3(5) . . ? C9 C8 Si1 119.5(4) . . ? C10 C9 C8 120.7(6) . . ? N2 C10 C9 124.1(6) . . ? N2 C11 C12 122.3(6) . . ? C11 C12 C8 122.1(6) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.542 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.090 data_P-HELIX _database_code_depnum_ccdc_archive 'CCDC 923409' #TrackingRef '04-P.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H26 Br2 Cu N2 O2 S2 Si' _chemical_formula_weight 593.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 11.94560(10) _cell_length_b 11.94560(10) _cell_length_c 16.2905(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2324.61(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4102 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 4.622 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3025 _exptl_absorpt_correction_T_max 0.3684 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Breeze CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10564 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.0989 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.98 _reflns_number_total 4952 _reflns_number_gt 4012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0955P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(16) _refine_ls_number_reflns 4952 _refine_ls_number_parameters 235 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1613 _refine_ls_wR_factor_gt 0.1426 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.45551(8) 0.16225(8) 0.12746(6) 0.0187(2) Uani 1 1 d . . . Si1 Si 0.32922(18) -0.34986(17) 0.27472(14) 0.0170(4) Uani 1 1 d . . . Br1 Br 0.29611(7) 0.23777(7) 0.20400(6) 0.0274(2) Uani 1 1 d . . . Br2 Br 0.50879(11) 0.10129(8) -0.00924(6) 0.0475(3) Uani 1 1 d . . . S1 S 0.6852(2) 0.0658(2) 0.22043(16) 0.0375(6) Uani 1 1 d . . . S2 S 0.0576(2) -0.1219(2) 0.2464(2) 0.0480(7) Uani 1 1 d . . . O1 O 0.5942(5) 0.1527(5) 0.2172(4) 0.0253(13) Uani 1 1 d . . . O2 O -0.0499(7) -0.0861(7) 0.2859(6) 0.062(2) Uani 1 1 d . . . N1 N 0.4117(5) 0.0053(5) 0.1637(4) 0.0198(14) Uani 1 1 d . . . N2 N 0.6833(6) -0.4936(6) 0.3465(4) 0.0240(15) Uani 1 1 d . . . C1 C 0.4094(7) -0.0131(6) 0.2453(5) 0.0189(16) Uani 1 1 d . . . H1A H 0.4272 0.0467 0.2815 0.023 Uiso 1 1 calc R . . C2 C 0.3819(7) -0.1162(7) 0.2780(5) 0.0199(17) Uani 1 1 d . . . H2A H 0.3793 -0.1243 0.3360 0.024 Uiso 1 1 calc R . . C3 C 0.3580(6) -0.2080(6) 0.2296(5) 0.0187(16) Uani 1 1 d . . . C4 C 0.3605(7) -0.1861(7) 0.1437(5) 0.0201(17) Uani 1 1 d . . . H4A H 0.3432 -0.2443 0.1060 0.024 Uiso 1 1 calc R . . C5 C 0.3876(7) -0.0814(6) 0.1149(5) 0.0212(17) Uani 1 1 d . . . H5A H 0.3893 -0.0700 0.0572 0.025 Uiso 1 1 calc R . . C6 C 0.2540(8) -0.3300(8) 0.3737(7) 0.034(2) Uani 1 1 d . . . H6A H 0.2389 -0.4032 0.3986 0.051 Uiso 1 1 calc R . . H6B H 0.1832 -0.2910 0.3637 0.051 Uiso 1 1 calc R . . H6C H 0.3005 -0.2854 0.4110 0.051 Uiso 1 1 calc R . . C7 C 0.2486(7) -0.4376(7) 0.2018(6) 0.0245(18) Uani 1 1 d . . . H7A H 0.2343 -0.5110 0.2266 0.037 Uiso 1 1 calc R . . H7B H 0.2918 -0.4473 0.1511 0.037 Uiso 1 1 calc R . . H7C H 0.1773 -0.4010 0.1892 0.037 Uiso 1 1 calc R . . C8 C 0.4723(7) -0.4107(7) 0.2979(5) 0.0186(16) Uani 1 1 d . . . C9 C 0.5027(7) -0.5213(7) 0.2871(6) 0.0255(19) Uani 1 1 d . . . H9A H 0.4513 -0.5714 0.2620 0.031 Uiso 1 1 calc R . . C10 C 0.6056(7) -0.5609(7) 0.3119(5) 0.0233(17) Uani 1 1 d . . . H10A H 0.6225 -0.6380 0.3043 0.028 Uiso 1 1 calc R . . C11 C 0.6544(8) -0.3852(8) 0.3559(7) 0.038(2) Uani 1 1 d . . . H11A H 0.7072 -0.3359 0.3803 0.045 Uiso 1 1 calc R . . C12 C 0.5536(8) -0.3425(7) 0.3326(6) 0.032(2) Uani 1 1 d . . . H12A H 0.5387 -0.2651 0.3401 0.038 Uiso 1 1 calc R . . C13 C 0.6920(11) 0.0205(13) 0.3241(9) 0.071(4) Uani 1 1 d . . . H13A H 0.6254 -0.0241 0.3371 0.107 Uiso 1 1 calc R . . H13B H 0.6950 0.0859 0.3604 0.107 Uiso 1 1 calc R . . H13C H 0.7592 -0.0252 0.3321 0.107 Uiso 1 1 calc R . . C14 C 0.8103(10) 0.1424(11) 0.2198(9) 0.064(4) Uani 1 1 d . . . H14A H 0.8233 0.1728 0.1648 0.096 Uiso 1 1 calc R . . H14B H 0.8726 0.0933 0.2351 0.096 Uiso 1 1 calc R . . H14C H 0.8050 0.2041 0.2593 0.096 Uiso 1 1 calc R . . C15 C 0.0193(11) -0.2132(9) 0.1659(7) 0.051(3) Uani 1 1 d . . . H15A H -0.0069 -0.2843 0.1890 0.076 Uiso 1 1 calc R . . H15B H 0.0843 -0.2268 0.1306 0.076 Uiso 1 1 calc R . . H15C H -0.0409 -0.1791 0.1335 0.076 Uiso 1 1 calc R . . C16 C 0.0994(10) -0.0063(10) 0.1863(9) 0.057(3) Uani 1 1 d . . . H16A H 0.1226 0.0551 0.2223 0.085 Uiso 1 1 calc R . . H16B H 0.0365 0.0183 0.1521 0.085 Uiso 1 1 calc R . . H16C H 0.1622 -0.0281 0.1510 0.085 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 0.0231(5) 0.0130(4) 0.0201(5) 0.0027(4) 0.0035(4) -0.0021(4) Si1 0.0171(11) 0.0128(10) 0.0212(11) 0.0031(9) 0.0002(9) 0.0012(8) Br1 0.0330(5) 0.0163(4) 0.0329(5) -0.0020(3) 0.0127(4) -0.0006(3) Br2 0.0848(9) 0.0250(5) 0.0327(5) -0.0030(4) 0.0328(6) -0.0091(5) S1 0.0469(14) 0.0235(11) 0.0421(15) 0.0001(10) -0.0135(12) 0.0064(10) S2 0.0452(15) 0.0418(14) 0.0570(17) -0.0046(14) -0.0185(14) 0.0056(12) O1 0.024(3) 0.019(3) 0.033(3) 0.008(2) -0.008(3) -0.001(2) O2 0.054(5) 0.051(5) 0.081(7) 0.001(4) 0.008(5) 0.009(4) N1 0.020(3) 0.015(3) 0.024(4) 0.005(3) 0.004(3) -0.001(3) N2 0.017(3) 0.028(4) 0.026(4) 0.000(3) -0.009(3) 0.004(3) C1 0.024(4) 0.014(4) 0.019(4) -0.003(3) 0.000(3) 0.000(3) C2 0.023(4) 0.025(4) 0.011(4) 0.002(3) -0.011(3) -0.001(3) C3 0.015(3) 0.011(3) 0.030(5) 0.000(3) 0.004(3) -0.002(3) C4 0.025(4) 0.016(4) 0.019(4) -0.005(3) -0.002(3) -0.002(3) C5 0.032(4) 0.020(4) 0.011(4) 0.002(3) 0.001(3) -0.004(3) C6 0.031(5) 0.030(5) 0.041(5) 0.012(4) 0.015(4) 0.001(4) C7 0.023(4) 0.016(4) 0.035(5) -0.002(4) 0.000(4) -0.009(3) C8 0.017(4) 0.025(4) 0.013(4) 0.001(3) -0.004(3) 0.000(3) C9 0.027(4) 0.018(4) 0.032(5) -0.003(4) -0.008(4) -0.002(4) C10 0.021(4) 0.022(4) 0.027(4) -0.002(4) -0.007(4) 0.006(3) C11 0.037(5) 0.026(5) 0.050(6) 0.005(4) -0.013(5) 0.002(4) C12 0.029(5) 0.018(4) 0.048(6) -0.001(4) -0.023(4) 0.000(4) C13 0.049(7) 0.089(10) 0.075(10) 0.053(9) -0.012(7) -0.018(7) C14 0.035(6) 0.073(9) 0.084(10) 0.030(8) 0.015(6) 0.005(6) C15 0.060(7) 0.030(6) 0.063(7) -0.003(5) 0.002(6) -0.004(5) C16 0.040(6) 0.042(6) 0.088(10) -0.001(7) 0.002(6) -0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.007(7) 4_664 ? Cu1 N1 2.034(6) . ? Cu1 O1 2.212(6) . ? Cu1 Br2 2.4278(13) . ? Cu1 Br1 2.4483(12) . ? Si1 C7 1.854(8) . ? Si1 C6 1.861(10) . ? Si1 C3 1.879(8) . ? Si1 C8 1.896(8) . ? S1 O1 1.503(6) . ? S1 C14 1.753(12) . ? S1 C13 1.776(13) . ? S2 O2 1.499(9) . ? S2 C16 1.765(12) . ? S2 C15 1.766(12) . ? N1 C5 1.337(10) . ? N1 C1 1.349(11) . ? N2 C11 1.349(12) . ? N2 C10 1.351(11) . ? N2 Cu1 2.007(7) 3_645 ? C1 C2 1.381(11) . ? C2 C3 1.380(11) . ? C3 C4 1.424(12) . ? C4 C5 1.375(11) . ? C8 C9 1.381(11) . ? C8 C12 1.387(11) . ? C9 C10 1.377(12) . ? C11 C12 1.362(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 176.6(3) 4_664 . ? N2 Cu1 O1 89.3(2) 4_664 . ? N1 Cu1 O1 87.3(2) . . ? N2 Cu1 Br2 88.0(2) 4_664 . ? N1 Cu1 Br2 93.3(2) . . ? O1 Cu1 Br2 113.21(17) . . ? N2 Cu1 Br1 91.4(2) 4_664 . ? N1 Cu1 Br1 89.53(19) . . ? O1 Cu1 Br1 105.37(17) . . ? Br2 Cu1 Br1 141.40(6) . . ? C7 Si1 C6 112.1(4) . . ? C7 Si1 C3 110.8(4) . . ? C6 Si1 C3 108.2(4) . . ? C7 Si1 C8 112.3(4) . . ? C6 Si1 C8 108.1(4) . . ? C3 Si1 C8 105.0(3) . . ? O1 S1 C14 104.8(5) . . ? O1 S1 C13 106.1(6) . . ? C14 S1 C13 97.2(6) . . ? O2 S2 C16 104.9(5) . . ? O2 S2 C15 105.9(6) . . ? C16 S2 C15 98.3(6) . . ? S1 O1 Cu1 126.9(4) . . ? C5 N1 C1 117.1(7) . . ? C5 N1 Cu1 126.6(6) . . ? C1 N1 Cu1 116.2(5) . . ? C11 N2 C10 116.3(7) . . ? C11 N2 Cu1 119.8(6) . 3_645 ? C10 N2 Cu1 123.8(6) . 3_645 ? N1 C1 C2 122.0(7) . . ? C3 C2 C1 122.5(7) . . ? C2 C3 C4 114.3(7) . . ? C2 C3 Si1 122.1(6) . . ? C4 C3 Si1 123.6(6) . . ? C5 C4 C3 120.5(7) . . ? N1 C5 C4 123.5(7) . . ? C9 C8 C12 115.4(8) . . ? C9 C8 Si1 125.4(6) . . ? C12 C8 Si1 119.1(6) . . ? C10 C9 C8 121.7(8) . . ? N2 C10 C9 122.1(8) . . ? N2 C11 C12 123.6(9) . . ? C11 C12 C8 120.8(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.817 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.126