# Electronic Supplementary Material (ESI) for Chemical Communications # 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_nth _database_code_depnum_ccdc_archive 'CCDC 830424' #TrackingRef '830424.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H41 Cl4 Cu2 N6 O2 Si2' _chemical_formula_weight 866.77 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Cubic _symmetry_space_group_name_H-M I-43d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' 'y+1/4, x+1/4, z+1/4' '-y+1/4, -x+3/4, z+3/4' 'y+3/4, -x+1/4, -z+3/4' '-y+3/4, x+3/4, -z+1/4' 'x+1/4, z+1/4, y+1/4' '-x+3/4, z+3/4, -y+1/4' '-x+1/4, -z+3/4, y+3/4' 'x+3/4, -z+1/4, -y+3/4' 'z+1/4, y+1/4, x+1/4' 'z+3/4, -y+1/4, -x+3/4' '-z+3/4, y+3/4, -x+1/4' '-z+1/4, -y+3/4, x+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-x+1/2, y+1, -z+1' 'x+1, -y+1, -z+1/2' 'z+1/2, x+1/2, y+1/2' 'z+1, -x+1, -y+1/2' '-z+1, -x+1/2, y+1' '-z+1/2, x+1, -y+1' 'y+1/2, z+1/2, x+1/2' '-y+1/2, z+1, -x+1' 'y+1, -z+1, -x+1/2' '-y+1, -z+1/2, x+1' 'y+3/4, x+3/4, z+3/4' '-y+3/4, -x+5/4, z+5/4' 'y+5/4, -x+3/4, -z+5/4' '-y+5/4, x+5/4, -z+3/4' 'x+3/4, z+3/4, y+3/4' '-x+5/4, z+5/4, -y+3/4' '-x+3/4, -z+5/4, y+5/4' 'x+5/4, -z+3/4, -y+5/4' 'z+3/4, y+3/4, x+3/4' 'z+5/4, -y+3/4, -x+5/4' '-z+5/4, y+5/4, -x+3/4' '-z+3/4, -y+5/4, x+5/4' _cell_length_a 30.848(4) _cell_length_b 30.848(4) _cell_length_c 30.848(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 29354(6) _cell_formula_units_Z 24 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3685 _cell_measurement_theta_min 4.18 _cell_measurement_theta_max 23.52 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 10680 _exptl_absorpt_coefficient_mu 1.167 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6101 _exptl_absorpt_correction_T_max 0.7917 _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 23561 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_unetI/netI 0.0733 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 26.48 _reflns_number_total 5065 _reflns_number_gt 2936 _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. The terminal carbon atoms of the vinyl group, owing to their high state of disorder, was restrained using DFIX and ISOR. ; _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^)+(0.0409P)^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 0.002(18) _refine_ls_number_reflns 5065 _refine_ls_number_parameters 236 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.002 _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 0.637973(18) 0.605723(19) 0.116177(19) 0.04815(17) Uani 1 1 d . . . Cl1 Cl 0.58185(5) 0.60940(5) 0.06771(5) 0.0791(5) Uani 1 1 d . . . Cl2 Cl 0.69410(4) 0.55667(4) 0.12445(5) 0.0611(3) Uani 1 1 d . . . Si1 Si 0.50244(7) 0.5000 0.2500 0.0487(5) Uani 1 2 d S . . Si2 Si 0.7500 0.75217(7) 0.0000 0.0503(5) Uani 1 2 d S . . O1 O 0.64514(13) 0.65108(11) 0.17055(10) 0.0607(10) Uani 1 1 d . . . N1 N 0.59893(12) 0.57150(11) 0.15650(12) 0.0457(10) Uani 1 1 d D . . N2 N 0.67421(13) 0.65020(13) 0.08325(12) 0.0451(10) Uani 1 1 d . . . N3 N 0.68696(17) 0.67395(17) 0.22500(15) 0.0726(14) Uani 1 1 d . . . C1 C 0.56650(17) 0.59333(15) 0.17644(18) 0.0601(15) Uani 1 1 d D . . H1 H 0.5637 0.6229 0.1713 0.072 Uiso 1 1 calc R . . C2 C 0.53783(17) 0.57364(18) 0.20369(17) 0.0560(15) Uani 1 1 d . . . H2 H 0.5165 0.5903 0.2170 0.067 Uiso 1 1 calc R . . C3 C 0.53955(16) 0.52928(16) 0.21211(16) 0.0461(13) Uani 1 1 d . . . C4 C 0.57307(16) 0.50720(17) 0.19047(15) 0.0512(13) Uani 1 1 d D . . H4 H 0.5759 0.4775 0.1945 0.061 Uiso 1 1 calc R . . C5 C 0.60109(16) 0.52764(12) 0.16422(15) 0.0535(14) Uani 1 1 d D . . H5 H 0.6228 0.5116 0.1507 0.064 Uiso 1 1 calc R . . C6 C 0.65358(17) 0.68271(17) 0.06367(17) 0.0578(14) Uani 1 1 d . . . H6 H 0.6235 0.6837 0.0652 0.069 Uiso 1 1 calc R . . C7 C 0.67510(18) 0.71506(18) 0.04111(18) 0.0599(16) Uani 1 1 d . . . H7 H 0.6592 0.7375 0.0288 0.072 Uiso 1 1 calc R . . C8 C 0.72034(17) 0.71468(16) 0.03650(16) 0.0458(13) Uani 1 1 d . . . C9 C 0.74053(17) 0.68090(18) 0.05890(17) 0.0586(15) Uani 1 1 d . . . H9 H 0.7706 0.6791 0.0589 0.070 Uiso 1 1 calc R . . C10 C 0.71686(17) 0.65030(18) 0.08095(16) 0.0552(14) Uani 1 1 d . . . H10 H 0.7318 0.6283 0.0951 0.066 Uiso 1 1 calc R . . C11 C 0.46819(19) 0.53905(19) 0.2808(2) 0.0660(17) Uani 1 1 d D . . H11A H 0.4496 0.5234 0.3002 0.079 Uiso 0.50 1 calc PR A 1 H11B H 0.4509 0.5556 0.2609 0.079 Uiso 0.50 1 calc PR A 1 H11C H 0.4865 0.5582 0.2971 0.079 Uiso 0.50 1 calc PR A 1 C12A C 0.4272(4) 0.5323(12) 0.2886(12) 0.080(11) Uani 0.25 1 d PDU B 2 H12A H 0.4063 0.5436 0.2701 0.096 Uiso 0.25 1 calc PR B 2 H12B H 0.4189 0.5162 0.3127 0.096 Uiso 0.25 1 calc PR B 2 C12B C 0.4268(3) 0.5423(14) 0.2732(13) 0.103(14) Uani 0.25 1 d PDU B 3 H12C H 0.4070 0.5293 0.2919 0.123 Uiso 0.25 1 calc PR B 3 H12D H 0.4170 0.5577 0.2492 0.123 Uiso 0.25 1 calc PR B 3 C13 C 0.71078(19) 0.78525(19) -0.0303(2) 0.0709(18) Uani 1 1 d D . . H13A H 0.6851 0.7720 -0.0389 0.085 Uiso 0.50 1 calc PR C 4 H13B H 0.6908 0.7666 -0.0453 0.085 Uiso 0.50 1 calc PR C 5 H13C H 0.7259 0.8029 -0.0510 0.085 Uiso 0.50 1 calc PR C 5 H13D H 0.6951 0.8035 -0.0106 0.085 Uiso 0.50 1 calc PR C 5 C14 C 0.7162(5) 0.8258(3) -0.0407(6) 0.141(7) Uani 0.50 1 d PD D 4 H14A H 0.7414 0.8401 -0.0327 0.169 Uiso 0.50 1 calc PR D 4 H14B H 0.6948 0.8403 -0.0561 0.169 Uiso 0.50 1 calc PR D 4 C17 C 0.6796(2) 0.65136(18) 0.19037(17) 0.0628(15) Uani 1 1 d . . . H17 H 0.7020 0.6342 0.1798 0.075 Uiso 1 1 calc R . . C18 C 0.6522(2) 0.7020(2) 0.2432(2) 0.094(2) Uani 1 1 d . . . H18A H 0.6632 0.7173 0.2680 0.113 Uiso 1 1 calc R . . H18B H 0.6280 0.6844 0.2517 0.113 Uiso 1 1 calc R . . H18C H 0.6431 0.7225 0.2216 0.113 Uiso 1 1 calc R . . C19 C 0.7286(2) 0.6704(3) 0.2496(2) 0.104(2) Uani 1 1 d . . . H19A H 0.7284 0.6904 0.2734 0.125 Uiso 1 1 calc R . . H19B H 0.7524 0.6770 0.2306 0.125 Uiso 1 1 calc R . . H19C H 0.7318 0.6414 0.2604 0.125 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 0.0493(4) 0.0519(4) 0.0433(4) 0.0023(3) -0.0070(3) 0.0093(3) Cl1 0.0758(10) 0.0774(10) 0.0842(11) 0.0281(9) -0.0432(8) -0.0147(9) Cl2 0.0537(8) 0.0601(9) 0.0695(9) 0.0102(7) 0.0000(7) 0.0160(6) Si1 0.0428(12) 0.0553(13) 0.0480(12) -0.0153(11) 0.000 0.000 Si2 0.0497(12) 0.0491(13) 0.0520(13) 0.000 -0.0101(10) 0.000 O1 0.067(3) 0.067(2) 0.048(2) -0.0097(18) -0.004(2) -0.002(2) N1 0.046(2) 0.052(3) 0.040(2) -0.005(2) -0.0035(19) 0.007(2) N2 0.043(3) 0.056(3) 0.036(2) 0.002(2) -0.0093(18) 0.007(2) N3 0.076(4) 0.091(4) 0.051(3) -0.016(3) 0.004(3) -0.027(3) C1 0.058(4) 0.053(3) 0.070(4) -0.001(3) 0.009(3) 0.015(3) C2 0.054(4) 0.057(4) 0.057(4) -0.011(3) 0.009(3) 0.014(3) C3 0.050(3) 0.047(3) 0.042(3) -0.010(3) -0.008(2) 0.005(2) C4 0.060(3) 0.053(3) 0.041(3) -0.001(3) -0.006(3) 0.005(3) C5 0.063(4) 0.051(3) 0.047(3) -0.007(3) -0.002(3) 0.025(3) C6 0.051(3) 0.060(4) 0.062(4) 0.002(3) -0.002(3) 0.011(3) C7 0.054(4) 0.055(4) 0.071(4) 0.008(3) -0.001(3) 0.015(3) C8 0.050(3) 0.050(3) 0.037(3) -0.010(2) -0.013(2) 0.009(2) C9 0.039(3) 0.074(4) 0.062(4) 0.003(3) -0.001(3) 0.008(3) C10 0.048(3) 0.065(4) 0.052(3) 0.013(3) -0.009(3) 0.010(3) C11 0.055(4) 0.074(4) 0.069(4) -0.025(3) 0.000(3) 0.003(3) C12A 0.069(14) 0.080(14) 0.089(15) 0.011(11) 0.012(9) 0.004(9) C12B 0.087(17) 0.116(18) 0.105(17) 0.004(11) 0.012(10) 0.021(10) C13 0.066(4) 0.048(4) 0.098(5) 0.013(3) -0.016(4) -0.014(3) C14 0.108(13) 0.100(13) 0.22(2) 0.016(14) -0.055(14) -0.022(11) C17 0.079(4) 0.067(4) 0.043(3) -0.011(3) 0.015(3) -0.016(3) C18 0.103(6) 0.087(5) 0.092(5) -0.033(4) -0.006(4) -0.009(4) C19 0.077(5) 0.139(7) 0.096(5) -0.043(5) 0.008(4) -0.037(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 N1 2.028(4) . ? Cu1 N2 2.041(4) . ? Cu1 O1 2.195(3) . ? Cu1 Cl1 2.2904(13) . ? Cu1 Cl2 2.3136(13) . ? Si1 C11 1.863(6) 28_455 ? Si1 C11 1.863(6) . ? Si1 C3 1.869(6) . ? Si1 C3 1.869(5) 28_455 ? Si2 C13 1.839(6) 27_644 ? Si2 C13 1.839(6) . ? Si2 C8 1.855(6) . ? Si2 C8 1.855(6) 27_644 ? O1 C17 1.226(6) . ? N1 C1 1.354(5) . ? N1 C5 1.375(3) . ? N2 C10 1.318(6) . ? N2 C6 1.332(6) . ? N3 C17 1.296(6) . ? N3 C18 1.488(7) . ? N3 C19 1.496(8) . ? C1 C2 1.363(7) . ? C1 H1 0.9300 . ? C2 C3 1.394(7) . ? C2 H2 0.9300 . ? C3 C4 1.407(7) . ? C4 C5 1.342(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.386(7) . ? C6 H6 0.9300 . ? C7 C8 1.403(7) . ? C7 H7 0.9300 . ? C8 C9 1.397(7) . ? C9 C10 1.374(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12A 1.303(5) . ? C11 C12B 1.303(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12A H12A 0.9300 . ? C12A H12B 0.9300 . ? C12B H12C 0.9300 . ? C12B H12D 0.9300 . ? C13 C14 1.300(5) . ? C13 H13A 0.9300 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13 H13D 0.9600 . ? C14 H14A 0.9300 . ? C14 H14B 0.9300 . ? C17 H17 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 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 168.74(14) . . ? N1 Cu1 O1 85.58(14) . . ? N2 Cu1 O1 84.07(13) . . ? N1 Cu1 Cl1 88.70(11) . . ? N2 Cu1 Cl1 93.20(11) . . ? O1 Cu1 Cl1 122.91(11) . . ? N1 Cu1 Cl2 92.08(11) . . ? N2 Cu1 Cl2 94.86(12) . . ? O1 Cu1 Cl2 104.90(11) . . ? Cl1 Cu1 Cl2 132.08(6) . . ? C11 Si1 C11 110.9(4) 28_455 . ? C11 Si1 C3 109.9(2) 28_455 . ? C11 Si1 C3 110.7(3) . . ? C11 Si1 C3 110.7(3) 28_455 28_455 ? C11 Si1 C3 109.9(2) . 28_455 ? C3 Si1 C3 104.5(3) . 28_455 ? C13 Si2 C13 112.6(4) 27_644 . ? C13 Si2 C8 111.2(2) 27_644 . ? C13 Si2 C8 109.3(3) . . ? C13 Si2 C8 109.3(3) 27_644 27_644 ? C13 Si2 C8 111.2(2) . 27_644 ? C8 Si2 C8 102.9(3) . 27_644 ? C17 O1 Cu1 118.2(3) . . ? C1 N1 C5 116.5(4) . . ? C1 N1 Cu1 117.3(3) . . ? C5 N1 Cu1 126.1(3) . . ? C10 N2 C6 116.8(5) . . ? C10 N2 Cu1 125.1(4) . . ? C6 N2 Cu1 118.0(3) . . ? C17 N3 C18 119.9(5) . . ? C17 N3 C19 121.9(6) . . ? C18 N3 C19 118.1(5) . . ? N1 C1 C2 122.5(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 121.9(5) . . ? C1 C2 H2 119.1 . . ? C3 C2 H2 119.1 . . ? C2 C3 C4 114.5(5) . . ? C2 C3 Si1 124.6(4) . . ? C4 C3 Si1 120.9(4) . . ? C5 C4 C3 122.2(5) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 N1 122.4(4) . . ? C4 C5 H5 118.8 . . ? N1 C5 H5 118.8 . . ? N2 C6 C7 122.7(5) . . ? N2 C6 H6 118.6 . . ? C7 C6 H6 118.6 . . ? C6 C7 C8 121.4(5) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 113.6(5) . . ? C9 C8 Si2 123.0(4) . . ? C7 C8 Si2 123.2(4) . . ? C10 C9 C8 121.4(5) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? N2 C10 C9 124.0(5) . . ? N2 C10 H10 118.0 . . ? C9 C10 H10 118.0 . . ? C12A C11 C12B 25(2) . . ? C12A C11 Si1 122.7(16) . . ? C12B C11 Si1 121.0(18) . . ? C12A C11 H11A 39.1 . . ? C12B C11 H11A 64.1 . . ? Si1 C11 H11A 109.5 . . ? C12A C11 H11B 70.4 . . ? C12B C11 H11B 45.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12A C11 H11C 124.8 . . ? C12B C11 H11C 128.4 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C11 C12A H12A 120.0 . . ? C11 C12A H12B 120.0 . . ? H12A C12A H12B 120.0 . . ? C11 C12B H12C 120.0 . . ? C11 C12B H12D 120.0 . . ? H12C C12B H12D 120.0 . . ? C14 C13 Si2 125.1(9) . . ? C14 C13 H13A 117.5 . . ? Si2 C13 H13A 117.5 . . ? C14 C13 H13B 122.7 . . ? Si2 C13 H13B 109.5 . . ? H13A C13 H13B 18.9 . . ? C14 C13 H13C 39.6 . . ? Si2 C13 H13C 109.5 . . ? H13A C13 H13C 118.3 . . ? H13B C13 H13C 109.5 . . ? C14 C13 H13D 69.9 . . ? Si2 C13 H13D 109.5 . . ? H13A C13 H13D 90.6 . . ? H13B C13 H13D 109.5 . . ? H13C C13 H13D 109.5 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? O1 C17 N3 124.5(6) . . ? O1 C17 H17 117.7 . . ? N3 C17 H17 117.7 . . ? N3 C18 H18A 109.5 . . ? N3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.268 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.059 # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.114 0.114 0.114 423 28 ' ' 2 0.114 -0.114 0.386 423 28 ' ' 3 0.386 -0.114 0.614 423 28 ' ' 4 0.386 0.114 0.886 423 28 ' ' 5 0.636 0.136 0.364 423 28 ' ' 6 0.864 0.136 0.636 423 28 ' ' 7 0.364 0.364 0.364 423 28 ' ' 8 0.136 0.364 0.636 423 28 ' ' 9 0.886 0.385 0.114 423 28 ' ' 10 0.614 0.386 0.886 423 28 ' ' 11 0.886 0.614 0.386 423 28 ' ' 12 0.614 0.614 0.614 423 28 ' ' 13 0.364 0.635 0.136 423 28 ' ' 14 0.136 0.635 0.864 423 28 ' ' 15 0.636 0.864 0.136 423 28 ' ' 16 0.864 0.864 0.864 423 28 ' ' _platon_squeeze_details ; ; data_cc _database_code_depnum_ccdc_archive 'CCDC 830425' #TrackingRef '830425.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H23 Cl2 Cu N2 O1.50 S1.50 Si' _chemical_formula_weight 477.98 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' '-y, x, z+1/4' '-x, -y, z+1/2' 'y, -x, z+3/4' _cell_length_a 11.9782(4) _cell_length_b 11.9782(4) _cell_length_c 15.7892(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2265.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1432 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 23.51 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 1.400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6475 _exptl_absorpt_correction_T_max 0.6952 _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_reflns_number 9394 _diffrn_reflns_av_R_equivalents 0.0951 _diffrn_reflns_av_unetI/netI 0.1231 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3563 _reflns_number_gt 2316 _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. The terminal carbon atoms of the vinyl group, owing to their high state of disorder, was restrained using DFIX and ISOR. ; _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^)+(0.0388P)^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 0.01(2) _refine_ls_number_reflns 3563 _refine_ls_number_parameters 291 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.95583(7) 0.32388(7) 0.1800(11) 0.0392(2) Uani 1 1 d . . . Cl1 Cl 0.81041(15) 0.24852(14) 0.1065(11) 0.0481(5) Uani 1 1 d . . . Cl2 Cl 1.0276(2) 0.39003(18) 0.3035(11) 0.0750(8) Uani 1 1 d . . . Si1 Si 0.82324(16) 0.83513(16) 0.0358(11) 0.0412(5) Uani 1 1 d . . . S1 S 1.1816(2) 0.4197(2) 0.0726(11) 0.0784(8) Uani 1 1 d . . . O1 O 1.0941(4) 0.3343(4) 0.0764(12) 0.0540(15) Uani 1 1 d . . . S2 S 1.3968(5) 0.5450(5) 0.2948(13) 0.106(2) Uani 0.50 1 d P . . O2 O 1.4295(8) 0.4514(9) 0.2532(14) 0.068(4) Uani 0.50 1 d P . . N1 N 0.9087(4) 0.4781(5) 0.1420(12) 0.0361(14) Uani 1 1 d . . . N2 N 1.1702(5) 0.9859(5) -0.0398(12) 0.0466(17) Uani 1 1 d . . . C1 C 0.8825(6) 0.5628(5) 0.1957(12) 0.0433(19) Uani 1 1 d . A . H1 H 0.8828 0.5493 0.2550 0.047 Uiso 1 1 calc R . . C2 C 0.9025(5) 0.4979(5) 0.0592(12) 0.0391(17) Uani 1 1 d . A . H2 H 0.9159 0.4380 0.0211 0.049 Uiso 1 1 calc R . . C3 C 0.8555(5) 0.6672(5) 0.1663(12) 0.0407(18) Uani 1 1 d . . . H3 H 0.8380 0.7241 0.2060 0.046 Uiso 1 1 calc R A . C4 C 0.8780(5) 0.5999(6) 0.0268(12) 0.0377(17) Uani 1 1 d . . . H4 H 0.8775 0.6100 -0.0329 0.048 Uiso 1 1 calc R A . C5 C 0.8531(5) 0.6924(6) 0.0803(12) 0.0376(17) Uani 1 1 d . A . C9 C 0.9626(5) 0.8978(6) 0.0084(12) 0.0389(17) Uani 1 1 d . A . C10 C 0.9886(6) 1.0097(6) 0.0195(12) 0.0433(19) Uani 1 1 d . . . H10 H 0.9352 1.0587 0.0438 0.053 Uiso 1 1 calc R A . C11 C 1.0471(7) 0.8304(7) -0.0275(13) 0.066(3) Uani 1 1 d . . . H11 H 1.0356 0.7527 -0.0358 0.077 Uiso 1 1 calc R A . C12 C 1.1469(6) 0.8798(6) -0.0504(13) 0.068(3) Uani 1 1 d . A . H12 H 1.2025 0.8338 -0.0754 0.071 Uiso 1 1 calc R . . C13 C 1.0911(6) 1.0498(6) -0.0044(12) 0.0448(19) Uani 1 1 d . A . H13 H 1.1068 1.1267 0.0045 0.055 Uiso 1 1 calc R . . C14 C 1.1865(8) 0.4619(7) -0.0365(13) 0.078(3) Uani 1 1 d . . . H14A H 1.1227 0.5104 -0.0489 0.085 Uiso 1 1 calc R . . H14B H 1.1833 0.3956 -0.0729 0.085 Uiso 1 1 calc R . . H14C H 1.2561 0.5025 -0.0472 0.085 Uiso 1 1 calc R . . C15 C 1.3094(6) 0.3429(9) 0.0725(14) 0.110(5) Uani 1 1 d . . . H15A H 1.3192 0.3061 0.1274 0.119 Uiso 1 1 calc R . . H15B H 1.3719 0.3940 0.0625 0.119 Uiso 1 1 calc R . . H15C H 1.3073 0.2865 0.0276 0.119 Uiso 1 1 calc R . . C16 C 1.5073(11) 0.5927(9) 0.3475(16) 0.047(4) Uani 0.50 1 d P . . H16A H 1.5658 0.6141 0.3073 0.170 Uiso 0.50 1 calc PR . . H16B H 1.5357 0.5341 0.3852 0.170 Uiso 0.50 1 calc PR . . H16C H 1.4856 0.6579 0.3812 0.170 Uiso 0.50 1 calc PR . . C17 C 1.3058(11) 0.5150(13) 0.3725(17) 0.059(5) Uani 0.50 1 d P . . H17A H 1.2372 0.4844 0.3479 0.194 Uiso 0.50 1 calc PR . . H17B H 1.2882 0.5832 0.4042 0.194 Uiso 0.50 1 calc PR . . H17C H 1.3389 0.4599 0.4109 0.194 Uiso 0.50 1 calc PR . . C6A C 0.729(6) 0.828(6) -0.080(5) 0.045(15) Uani 0.20 1 d PU A 1 H6A H 0.7581 0.7676 -0.1159 0.067 Uiso 0.20 1 calc PR A 1 H6B H 0.7354 0.8990 -0.1101 0.067 Uiso 0.20 1 calc PR A 1 H6C H 0.6502 0.8131 -0.0670 0.067 Uiso 0.20 1 calc PR A 1 C8B C 0.7563(7) 0.807(2) -0.1235(3) 0.073(8) Uani 0.40 1 d PDU A 2 H8C H 0.8340 0.7951 -0.1313 0.088 Uiso 0.40 1 calc PR A 2 H8D H 0.7069 0.8030 -0.1705 0.088 Uiso 0.40 1 calc PR A 2 C7B C 0.717(2) 0.830(2) -0.0473(3) 0.044(8) Uani 0.40 1 d PDU A 2 H7B H 0.6398 0.8429 -0.0365 0.053 Uiso 0.40 1 calc PR A 2 C7A C 0.7599(3) 0.8127(19) -0.068(2) 0.025(5) Uani 0.40 1 d PDU A 3 H7A H 0.8028 0.7782 -0.1113 0.030 Uiso 0.40 1 calc PR A 3 C8A C 0.6561(11) 0.843(2) -0.085(3) 0.088(9) Uani 0.40 1 d PDU A 3 H8A H 0.6121 0.8777 -0.0421 0.106 Uiso 0.40 1 calc PR A 3 H8B H 0.6255 0.8302 -0.1394 0.106 Uiso 0.40 1 calc PR A 3 C6B C 0.7399(11) 0.9235(14) 0.1164(17) 0.053(4) Uani 0.80 1 d P A 3 H6D H 0.6608 0.9027 0.1138 0.079 Uiso 0.80 1 calc PR A 3 H6E H 0.7481 1.0028 0.1026 0.079 Uiso 0.80 1 calc PR A 3 H6F H 0.7685 0.9096 0.1736 0.079 Uiso 0.80 1 calc PR A 3 C8C C 0.6621(3) 0.954(2) 0.101(3) 0.029(7) Uani 0.20 1 d PDU A 1 H8E H 0.6186 0.9341 0.0526 0.035 Uiso 0.20 1 calc PR A 1 H8F H 0.6312 1.0005 0.1433 0.035 Uiso 0.20 1 calc PR A 1 C7C C 0.7654(19) 0.916(4) 0.108(4) 0.012(9) Uani 0.20 1 d PDU A 1 H7C H 0.8078 0.9370 0.1566 0.015 Uiso 0.20 1 calc PR A 1 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 0.0411(5) 0.0369(5) 0.0396(6) 0.0068(4) -0.0035(4) 0.0038(4) Cl1 0.0504(11) 0.0394(10) 0.0544(14) 0.0005(9) -0.0135(10) 0.0001(8) Cl2 0.1135(19) 0.0568(13) 0.0547(17) 0.0009(11) -0.0418(15) 0.0199(13) Si1 0.0377(11) 0.0390(11) 0.0470(15) 0.0110(10) -0.0055(10) -0.0067(8) S1 0.0844(18) 0.0707(15) 0.080(2) 0.0037(14) 0.0039(15) -0.0188(14) O1 0.055(3) 0.048(3) 0.059(4) 0.020(3) 0.000(3) -0.003(2) S2 0.078(4) 0.072(4) 0.168(8) 0.013(4) -0.024(4) -0.006(3) O2 0.045(6) 0.049(7) 0.109(12) -0.008(7) -0.024(7) 0.011(5) N1 0.043(3) 0.040(3) 0.026(4) 0.002(3) 0.000(3) 0.000(3) N2 0.049(4) 0.038(3) 0.052(5) 0.004(3) 0.016(3) -0.006(3) C1 0.055(4) 0.041(4) 0.034(5) 0.005(4) -0.009(4) 0.007(3) C2 0.046(4) 0.032(4) 0.039(5) 0.001(3) 0.001(4) -0.002(3) C3 0.044(4) 0.036(4) 0.043(6) -0.004(3) 0.002(4) 0.007(3) C4 0.037(4) 0.044(4) 0.032(5) 0.008(3) -0.002(3) -0.005(3) C5 0.029(3) 0.049(4) 0.035(5) 0.002(4) -0.006(3) -0.010(3) C9 0.036(4) 0.044(4) 0.037(5) 0.004(3) 0.003(3) -0.004(3) C10 0.046(4) 0.035(4) 0.049(6) -0.001(4) 0.014(4) -0.001(3) C11 0.059(5) 0.037(4) 0.103(8) -0.005(5) 0.030(5) -0.011(4) C12 0.051(5) 0.038(4) 0.115(9) -0.016(5) 0.042(5) -0.004(3) C13 0.047(4) 0.039(4) 0.048(6) -0.003(4) 0.011(4) -0.001(3) C14 0.092(7) 0.060(6) 0.083(9) 0.027(5) 0.020(6) -0.004(5) C15 0.024(4) 0.152(10) 0.154(13) 0.072(10) -0.024(6) -0.026(5) C16 0.048(8) 0.010(6) 0.082(13) -0.002(7) -0.018(9) -0.002(5) C17 0.029(8) 0.051(9) 0.096(17) 0.000(9) -0.001(9) -0.002(7) C6A 0.05(2) 0.05(2) 0.03(2) -0.012(18) 0.012(19) 0.000(17) C8B 0.064(13) 0.076(14) 0.080(17) -0.001(14) 0.002(12) 0.026(12) C7B 0.048(11) 0.047(10) 0.038(11) 0.008(8) -0.001(8) 0.006(8) C7A 0.036(9) 0.021(7) 0.018(9) 0.003(7) 0.001(8) 0.013(7) C8A 0.099(15) 0.083(16) 0.083(17) 0.012(13) -0.032(14) 0.003(13) C6B 0.041(7) 0.051(7) 0.066(10) 0.011(6) 0.013(9) 0.002(7) C8C 0.022(13) 0.016(12) 0.049(17) 0.020(12) 0.014(12) -0.001(10) C7C 0.012(9) 0.012(9) 0.012(9) 0.0000(10) 0.0000(10) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.023(6) . ? Cu1 N2 2.026(5) 2_745 ? Cu1 Cl2 2.274(3) . ? Cu1 Cl1 2.280(2) . ? Cu1 O1 2.331(5) . ? Si1 C7C 1.65(5) . ? Si1 C7A 1.83(3) . ? Si1 C7B 1.83(2) . ? Si1 C9 1.880(7) . ? Si1 C5 1.883(7) . ? Si1 C6B 1.933(16) . ? Si1 C6A 2.15(7) . ? S1 O1 1.465(5) . ? S1 C15 1.786(9) . ? S1 C14 1.796(10) . ? S2 O2 1.357(12) . ? S2 C16 1.665(14) . ? S2 C17 1.682(18) . ? N1 C2 1.330(9) . ? N1 C1 1.359(9) . ? N2 C12 1.311(9) . ? N2 C13 1.340(8) . ? N2 Cu1 2.026(5) 4_674 ? C1 C3 1.372(9) . ? C1 H1 0.9500 . ? C2 C4 1.357(9) . ? C2 H2 0.9500 . ? C3 C5 1.391(10) . ? C3 H3 0.9500 . ? C4 C5 1.424(10) . ? C4 H4 0.9500 . ? C9 C10 1.388(10) . ? C9 C11 1.414(11) . ? C10 C13 1.372(9) . ? C10 H10 0.9500 . ? C11 C12 1.381(10) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C6A H6A 0.9800 . ? C6A H6B 0.9800 . ? C6A H6C 0.9800 . ? C8B C7B 1.32199(14) . ? C8B H8C 0.9500 . ? C8B H8D 0.9500 . ? C7B H7B 0.9500 . ? C7A C8A 1.32200(12) . ? C7A H7A 0.9500 . ? C8A H8A 0.9500 . ? C8A H8B 0.9500 . ? C6B H6D 0.9800 . ? C6B H6E 0.9800 . ? C6B H6F 0.9800 . ? C8C C7C 1.3220(3) . ? C8C H8E 0.9500 . ? C8C H8F 0.9500 . ? C7C H7C 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 174.8(3) . 2_745 ? N1 Cu1 Cl2 92.40(18) . . ? N2 Cu1 Cl2 89.1(2) 2_745 . ? N1 Cu1 Cl1 89.83(17) . . ? N2 Cu1 Cl1 91.33(19) 2_745 . ? Cl2 Cu1 Cl1 149.73(10) . . ? N1 Cu1 O1 86.6(2) . . ? N2 Cu1 O1 88.2(2) 2_745 . ? Cl2 Cu1 O1 108.33(16) . . ? Cl1 Cu1 O1 101.94(15) . . ? C7C Si1 C7A 122.2(14) . . ? C7C Si1 C7B 102.9(14) . . ? C7A Si1 C7B 20.3(7) . . ? C7C Si1 C9 107.2(17) . . ? C7A Si1 C9 102.8(6) . . ? C7B Si1 C9 117.8(8) . . ? C7C Si1 C5 111(2) . . ? C7A Si1 C5 106.3(7) . . ? C7B Si1 C5 111.7(9) . . ? C9 Si1 C5 106.2(3) . . ? C7C Si1 C6B 6.4(17) . . ? C7A Si1 C6B 117.2(7) . . ? C7B Si1 C6B 97.5(8) . . ? C9 Si1 C6B 113.1(5) . . ? C5 Si1 C6B 110.5(6) . . ? C7C Si1 C6A 113(2) . . ? C7A Si1 C6A 9(2) . . ? C7B Si1 C6A 12(2) . . ? C9 Si1 C6A 107(2) . . ? C5 Si1 C6A 112(2) . . ? C6B Si1 C6A 108(2) . . ? O1 S1 C15 104.7(4) . . ? O1 S1 C14 105.0(4) . . ? C15 S1 C14 96.7(5) . . ? S1 O1 Cu1 125.0(3) . . ? O2 S2 C16 107.2(8) . . ? O2 S2 C17 111.3(9) . . ? C16 S2 C17 102.9(10) . . ? C2 N1 C1 117.9(6) . . ? C2 N1 Cu1 118.0(5) . . ? C1 N1 Cu1 124.1(5) . . ? C12 N2 C13 117.2(6) . . ? C12 N2 Cu1 119.8(5) . 4_674 ? C13 N2 Cu1 122.9(5) . 4_674 ? N1 C1 C3 121.6(7) . . ? N1 C1 H1 119.2 . . ? C3 C1 H1 119.2 . . ? N1 C2 C4 122.9(7) . . ? N1 C2 H2 118.6 . . ? C4 C2 H2 118.6 . . ? C1 C3 C5 122.1(7) . . ? C1 C3 H3 118.9 . . ? C5 C3 H3 118.9 . . ? C2 C4 C5 121.4(7) . . ? C2 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C3 C5 C4 114.0(6) . . ? C3 C5 Si1 124.4(5) . . ? C4 C5 Si1 121.6(6) . . ? C10 C9 C11 116.2(6) . . ? C10 C9 Si1 123.8(6) . . ? C11 C9 Si1 120.0(5) . . ? C13 C10 C9 120.3(7) . . ? C13 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C9 118.7(7) . . ? C12 C11 H11 120.7 . . ? C9 C11 H11 120.7 . . ? N2 C12 C11 124.5(7) . . ? N2 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? N2 C13 C10 123.2(7) . . ? N2 C13 H13 118.4 . . ? C10 C13 H13 118.4 . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S2 C16 H16A 109.5 . . ? S2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? S2 C17 H17A 109.5 . . ? S2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si1 C6A H6A 109.5 . . ? Si1 C6A H6B 109.5 . . ? Si1 C6A H6C 109.5 . . ? C7B C8B H8C 120.0 . . ? C7B C8B H8D 120.0 . . ? H8C C8B H8D 120.0 . . ? C8B C7B Si1 114.2(15) . . ? C8B C7B H7B 122.9 . . ? Si1 C7B H7B 122.9 . . ? C8A C7A Si1 122(2) . . ? C8A C7A H7A 119.0 . . ? Si1 C7A H7A 119.0 . . ? C7A C8A H8A 120.0 . . ? C7A C8A H8B 120.0 . . ? H8A C8A H8B 120.0 . . ? Si1 C6B H6D 109.5 . . ? Si1 C6B H6E 109.5 . . ? Si1 C6B H6F 109.5 . . ? C7C C8C H8E 120.0 . . ? C7C C8C H8F 120.0 . . ? H8E C8C H8F 120.0 . . ? C8C C7C Si1 122(4) . . ? C8C C7C H7C 119.0 . . ? Si1 C7C H7C 119.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.763 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.088 data_yy _database_code_depnum_ccdc_archive 'CCDC 830426' #TrackingRef '830426.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 Cl2 Cu N2 O2 S2 Si' _chemical_formula_weight 517.05 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 12.0129(2) _cell_length_b 12.0129(2) _cell_length_c 15.8085(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2281.32(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3413 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 24.47 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 1.442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5893 _exptl_absorpt_correction_T_max 0.8347 _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_reflns_number 10215 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_unetI/netI 0.0710 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.49 _reflns_number_total 4577 _reflns_number_gt 3632 _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. The terminal carbon atoms (C(8A), C(8B), C(8C)) of the vinyl group, owing to their high state of disorder, was restrained using DFIX and ISOR. ; _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^)+(0.0715P)^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 0.000(19) _refine_ls_number_reflns 4577 _refine_ls_number_parameters 262 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1237 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.009 _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 -0.17593(5) 0.54466(5) 0.12353(4) 0.03649(18) Uani 1 1 d . . . Cl1 Cl -0.25102(11) 0.68974(12) 0.19757(9) 0.0450(3) Uani 1 1 d . . . Cl2 Cl -0.11024(15) 0.47471(18) -0.00041(11) 0.0723(6) Uani 1 1 d . . . Si1 Si 0.33463(13) 0.67511(13) 0.26768(10) 0.0391(4) Uani 1 1 d . B . S1 S -0.07986(17) 0.31793(17) 0.22986(14) 0.0698(5) Uani 1 1 d . . . S2 S 0.1054(4) 0.9550(5) 0.2579(5) 0.196(2) Uani 1 1 d . . . O1 O -0.1642(4) 0.4073(3) 0.2251(3) 0.0527(11) Uani 1 1 d . . . O2 O 0.0718(7) 1.0543(6) 0.2996(6) 0.143(4) Uani 1 1 d . . . N1 N -0.0214(4) 0.5930(4) 0.1605(3) 0.0346(10) Uani 1 1 d . . . N2 N 0.4876(4) 0.3286(4) 0.3425(3) 0.0403(11) Uani 1 1 d . B . C1 C -0.0007(5) 0.5972(4) 0.2440(3) 0.0370(12) Uani 1 1 d . . . H1A H -0.0603 0.5825 0.2819 0.044 Uiso 1 1 calc R . . C2 C 0.0626(4) 0.6167(5) 0.1090(3) 0.0385(12) Uani 1 1 d . . . H2A H 0.0496 0.6142 0.0498 0.046 Uiso 1 1 calc R . . C3 C 0.1678(4) 0.6446(4) 0.1369(3) 0.0383(12) Uani 1 1 d . . . H3A H 0.2244 0.6626 0.0972 0.046 Uiso 1 1 calc R . . C4 C 0.1021(4) 0.6216(4) 0.2776(3) 0.0364(12) Uani 1 1 d . . . H4A H 0.1123 0.6216 0.3372 0.044 Uiso 1 1 calc R . . C5 C 0.1915(4) 0.6464(4) 0.2244(3) 0.0353(11) Uani 1 1 d . . . C6 C 0.3201(6) 0.7530(7) 0.3676(5) 0.078(2) Uani 1 1 d D . . H6A H 0.2741 0.7102 0.4071 0.094 Uiso 0.50 1 calc PR A 1 H6B H 0.2847 0.8250 0.3563 0.094 Uiso 0.50 1 calc PR A 1 H6C H 0.3939 0.7652 0.3924 0.094 Uiso 0.50 1 calc PR A 1 H6D H 0.3378 0.8285 0.3558 0.094 Uiso 0.25 1 calc PR A 2 H6E H 0.2795 0.7135 0.4095 0.094 Uiso 0.25 1 calc PR A 3 C8B C 0.295(3) 0.747(3) 0.4485(8) 0.085(9) Uani 0.25 1 d PDU B 2 H8C H 0.3107 0.8080 0.4848 0.102 Uiso 0.25 1 calc PR B 2 H8D H 0.2620 0.6813 0.4707 0.102 Uiso 0.25 1 calc PR B 2 C8C C 0.354(2) 0.8515(13) 0.393(2) 0.078(9) Uani 0.25 1 d PDU B 3 H8E H 0.3465 0.8718 0.4512 0.094 Uiso 0.25 1 calc PR B 3 H8F H 0.3858 0.9023 0.3542 0.094 Uiso 0.25 1 calc PR B 3 C7 C 0.4212(5) 0.7489(5) 0.1881(4) 0.0518(15) Uani 1 1 d D . . H7D H 0.4405 0.7136 0.1364 0.062 Uiso 0.50 1 calc PR B 1 H7A H 0.4953 0.7632 0.2118 0.062 Uiso 0.50 1 calc PR B 2 H7B H 0.3858 0.8198 0.1733 0.062 Uiso 0.50 1 calc PR B 2 H7C H 0.4283 0.7027 0.1373 0.062 Uiso 0.50 1 calc PR B 2 C8A C 0.4556(15) 0.8507(8) 0.2044(13) 0.098(6) Uani 0.50 1 d PDU B 1 H8A H 0.4361 0.8855 0.2562 0.117 Uiso 0.50 1 calc PR B 1 H8B H 0.5000 0.8893 0.1642 0.117 Uiso 0.50 1 calc PR B 1 C9 C 0.3973(5) 0.5356(5) 0.2950(3) 0.0391(12) Uani 1 1 d . . . C10 C 0.5089(5) 0.5093(5) 0.2841(4) 0.0410(13) Uani 1 1 d . B . H10A H 0.5574 0.5622 0.2589 0.049 Uiso 1 1 calc R . . C11 C 0.3328(5) 0.4529(6) 0.3303(5) 0.065(2) Uani 1 1 d . B . H11A H 0.2555 0.4652 0.3391 0.078 Uiso 1 1 calc R . . C12 C 0.3802(5) 0.3520(6) 0.3532(5) 0.0627(19) Uani 1 1 d . . . H12A H 0.3336 0.2968 0.3778 0.075 Uiso 1 1 calc R B . C13 C 0.5504(5) 0.4081(5) 0.3094(4) 0.0408(13) Uani 1 1 d . . . H13A H 0.6278 0.3945 0.3028 0.049 Uiso 1 1 calc R B . C14 C -0.0360(7) 0.3103(7) 0.3376(5) 0.075(2) Uani 1 1 d . . . H14A H 0.0126 0.3736 0.3504 0.089 Uiso 1 1 calc R . . H14B H 0.0048 0.2407 0.3468 0.089 Uiso 1 1 calc R . . H14C H -0.1013 0.3124 0.3747 0.089 Uiso 1 1 calc R . . C15 C -0.1631(8) 0.1907(6) 0.2343(6) 0.094(3) Uani 1 1 d . . . H15A H -0.1966 0.1768 0.1788 0.112 Uiso 1 1 calc R . . H15B H -0.2220 0.1994 0.2767 0.112 Uiso 1 1 calc R . . H15C H -0.1152 0.1279 0.2499 0.112 Uiso 1 1 calc R . . C16 C -0.0075(8) 0.9043(8) 0.2055(8) 0.115(4) Uani 1 1 d . . . H16A H -0.0652 0.8837 0.2463 0.138 Uiso 1 1 calc R . . H16B H 0.0143 0.8386 0.1727 0.138 Uiso 1 1 calc R . . H16C H -0.0365 0.9616 0.1672 0.138 Uiso 1 1 calc R . . C17 C 0.1983(8) 0.9819(10) 0.1806(8) 0.117(4) Uani 1 1 d . . . H17A H 0.2665 1.0122 0.2056 0.140 Uiso 1 1 calc R . . H17B H 0.1667 1.0362 0.1411 0.140 Uiso 1 1 calc R . . H17C H 0.2156 0.9129 0.1503 0.140 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 0.0362(4) 0.0388(4) 0.0344(3) -0.0032(3) -0.0063(3) -0.0042(3) Cl1 0.0397(7) 0.0483(8) 0.0469(8) -0.0105(6) -0.0012(6) -0.0006(6) Cl2 0.0550(10) 0.1096(15) 0.0525(10) -0.0425(10) 0.0011(8) -0.0214(10) Si1 0.0367(8) 0.0375(8) 0.0431(8) -0.0054(6) -0.0109(7) 0.0061(6) S1 0.0639(11) 0.0748(13) 0.0707(12) 0.0039(10) -0.0044(9) 0.0175(10) S2 0.147(4) 0.162(4) 0.279(7) 0.027(4) -0.037(4) -0.020(3) O1 0.059(3) 0.041(2) 0.057(2) 0.0050(19) -0.019(2) 0.0003(19) O2 0.154(7) 0.089(5) 0.186(9) -0.038(5) -0.038(6) 0.053(5) N1 0.038(2) 0.038(2) 0.028(2) -0.0003(18) -0.0038(19) -0.0016(19) N2 0.034(2) 0.042(3) 0.045(3) 0.009(2) -0.002(2) 0.005(2) C1 0.040(3) 0.040(3) 0.032(3) 0.001(2) -0.001(2) -0.002(2) C2 0.041(3) 0.049(3) 0.025(3) -0.006(2) -0.005(2) -0.003(2) C3 0.039(3) 0.044(3) 0.032(3) -0.005(2) 0.004(2) -0.004(2) C4 0.045(3) 0.035(3) 0.030(3) 0.001(2) -0.010(2) 0.004(2) C5 0.036(3) 0.029(3) 0.041(3) -0.005(2) -0.004(2) 0.006(2) C6 0.052(4) 0.101(6) 0.082(5) -0.041(5) -0.025(4) 0.022(4) C8B 0.100(16) 0.060(14) 0.094(16) 0.013(13) -0.040(14) -0.018(12) C8C 0.059(13) 0.098(16) 0.077(15) -0.025(13) -0.008(12) 0.010(13) C7 0.042(3) 0.050(4) 0.064(4) 0.006(3) -0.014(3) 0.009(3) C8A 0.089(10) 0.100(10) 0.104(11) 0.043(9) -0.028(9) -0.005(9) C9 0.041(3) 0.041(3) 0.035(3) 0.003(2) -0.004(2) 0.006(3) C10 0.038(3) 0.041(3) 0.044(3) 0.010(3) 0.001(2) 0.003(2) C11 0.035(3) 0.061(4) 0.099(5) 0.031(4) 0.007(3) 0.011(3) C12 0.043(3) 0.059(4) 0.086(5) 0.029(4) 0.010(3) 0.011(3) C13 0.038(3) 0.039(3) 0.046(3) 0.004(2) 0.003(2) 0.006(2) C14 0.072(5) 0.074(5) 0.078(5) 0.018(4) -0.031(4) -0.006(4) C15 0.116(7) 0.043(4) 0.122(8) -0.007(4) -0.054(6) 0.012(4) C16 0.092(7) 0.070(6) 0.183(12) 0.006(7) -0.034(8) -0.004(5) C17 0.067(6) 0.125(9) 0.158(11) 0.034(8) -0.003(7) -0.006(6) _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 2.018(4) 3_554 ? Cu1 N1 2.031(4) . ? Cu1 Cl2 2.2733(17) . ? Cu1 Cl1 2.2850(15) . ? Cu1 O1 2.307(4) . ? Si1 C6 1.844(8) . ? Si1 C7 1.857(7) . ? Si1 C5 1.882(5) . ? Si1 C9 1.888(6) . ? S1 O1 1.477(5) . ? S1 C14 1.785(8) . ? S1 C15 1.827(8) . ? S2 O2 1.422(9) . ? S2 C17 1.686(12) . ? S2 C16 1.701(11) . ? N1 C2 1.327(7) . ? N1 C1 1.344(7) . ? N2 C13 1.324(7) . ? N2 C12 1.333(7) . ? N2 Cu1 2.018(4) 4 ? C1 C4 1.376(7) . ? C1 H1A 0.9500 . ? C2 C3 1.381(7) . ? C2 H2A 0.9500 . ? C3 C5 1.412(8) . ? C3 H3A 0.9500 . ? C4 C5 1.397(8) . ? C4 H4A 0.9500 . ? C6 C8B 1.316(4) . ? C6 C8C 1.316(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C6 H6D 0.9500 . ? C6 H6E 0.9500 . ? C8B H8C 0.9500 . ? C8B H8D 0.9500 . ? C8C H8E 0.9500 . ? C8C H8F 0.9500 . ? C7 C8A 1.316(4) . ? C7 H7D 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8A H8A 0.9500 . ? C8A H8B 0.9500 . ? C9 C11 1.378(9) . ? C9 C10 1.388(8) . ? C10 C13 1.373(8) . ? C10 H10A 0.9500 . ? C11 C12 1.387(8) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 176.02(19) 3_554 . ? N2 Cu1 Cl2 88.86(14) 3_554 . ? N1 Cu1 Cl2 92.08(13) . . ? N2 Cu1 Cl1 91.42(14) 3_554 . ? N1 Cu1 Cl1 89.73(13) . . ? Cl2 Cu1 Cl1 149.37(8) . . ? N2 Cu1 O1 88.99(17) 3_554 . ? N1 Cu1 O1 87.05(16) . . ? Cl2 Cu1 O1 108.31(13) . . ? Cl1 Cu1 O1 102.32(12) . . ? C6 Si1 C7 113.0(4) . . ? C6 Si1 C5 108.6(3) . . ? C7 Si1 C5 110.7(3) . . ? C6 Si1 C9 107.0(3) . . ? C7 Si1 C9 110.8(3) . . ? C5 Si1 C9 106.5(2) . . ? O1 S1 C14 106.7(3) . . ? O1 S1 C15 103.6(3) . . ? C14 S1 C15 94.7(4) . . ? O2 S2 C17 111.3(7) . . ? O2 S2 C16 107.5(6) . . ? C17 S2 C16 104.1(7) . . ? S1 O1 Cu1 126.7(3) . . ? C2 N1 C1 117.0(5) . . ? C2 N1 Cu1 125.4(3) . . ? C1 N1 Cu1 117.5(4) . . ? C13 N2 C12 116.7(5) . . ? C13 N2 Cu1 124.0(4) . 4 ? C12 N2 Cu1 119.3(4) . 4 ? N1 C1 C4 123.6(5) . . ? N1 C1 H1A 118.2 . . ? C4 C1 H1A 118.2 . . ? N1 C2 C3 123.5(5) . . ? N1 C2 H2A 118.2 . . ? C3 C2 H2A 118.2 . . ? C2 C3 C5 120.1(5) . . ? C2 C3 H3A 119.9 . . ? C5 C3 H3A 119.9 . . ? C1 C4 C5 120.2(5) . . ? C1 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? C4 C5 C3 115.6(5) . . ? C4 C5 Si1 121.5(4) . . ? C3 C5 Si1 122.9(4) . . ? C8B C6 C8C 80(2) . . ? C8B C6 Si1 145.7(17) . . ? C8C C6 Si1 133.9(17) . . ? C8B C6 H6A 39.0 . . ? C8C C6 H6A 116.6 . . ? Si1 C6 H6A 109.5 . . ? C8B C6 H6B 97.3 . . ? C8C C6 H6B 52.9 . . ? Si1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C8B C6 H6C 79.9 . . ? C8C C6 H6C 57.5 . . ? Si1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8B C6 H6D 107.2 . . ? C8C C6 H6D 29.9 . . ? Si1 C6 H6D 107.2 . . ? H6A C6 H6D 138.8 . . ? H6B C6 H6D 38.7 . . ? H6C C6 H6D 74.5 . . ? C8B C6 H6E 34.7 . . ? C8C C6 H6E 113.1 . . ? Si1 C6 H6E 113.1 . . ? H6A C6 H6E 4.7 . . ? H6B C6 H6E 110.1 . . ? H6C C6 H6E 105.1 . . ? H6D C6 H6E 136.8 . . ? C6 C8B H8C 120.0 . . ? C6 C8B H8D 120.0 . . ? H8C C8B H8D 120.0 . . ? C6 C8C H8E 120.0 . . ? C6 C8C H8F 120.0 . . ? H8E C8C H8F 120.0 . . ? C8A C7 Si1 119.2(11) . . ? C8A C7 H7D 120.4 . . ? Si1 C7 H7D 120.4 . . ? C8A C7 H7A 58.5 . . ? Si1 C7 H7A 109.5 . . ? H7D C7 H7A 100.7 . . ? C8A C7 H7B 51.4 . . ? Si1 C7 H7B 109.5 . . ? H7D C7 H7B 106.7 . . ? H7A C7 H7B 109.5 . . ? C8A C7 H7C 131.2 . . ? Si1 C7 H7C 109.5 . . ? H7D C7 H7C 11.6 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C7 C8A H8A 120.0 . . ? C7 C8A H8B 120.0 . . ? H8A C8A H8B 120.0 . . ? C11 C9 C10 115.5(5) . . ? C11 C9 Si1 120.5(4) . . ? C10 C9 Si1 124.0(4) . . ? C13 C10 C9 121.0(5) . . ? C13 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C9 C11 C12 120.3(6) . . ? C9 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? N2 C12 C11 123.3(6) . . ? N2 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? N2 C13 C10 123.2(5) . . ? N2 C13 H13A 118.4 . . ? C10 C13 H13A 118.4 . . ? S1 C14 H14A 109.5 . . ? S1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? S2 C16 H16A 109.5 . . ? S2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? S2 C17 H17A 109.5 . . ? S2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? S2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.890 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.090