# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_a20109c _database_code_depnum_ccdc_archive 'CCDC 876103' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SiR-Hg _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37.50 H44 Cl N5 O S Si' _chemical_formula_weight 676.38 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 30.130(6) _cell_length_b 13.543(3) _cell_length_c 19.002(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7754(3) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 928 _cell_measurement_theta_min 2.248 _cell_measurement_theta_max 27.27 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2872 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29442 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6850 _reflns_number_gt 4712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1366P)^2^+6.1561P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6850 _refine_ls_number_parameters 456 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.2543 _refine_ls_wR_factor_gt 0.2260 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.70395(16) 0.3961(5) 0.1288(3) 0.0957(18) Uani 1 1 d . . . H1A H 0.6999 0.4659 0.1166 0.144 Uiso 1 1 calc R . . H1B H 0.7032 0.3561 0.0859 0.144 Uiso 1 1 calc R . . H1C H 0.7326 0.3875 0.1524 0.144 Uiso 1 1 calc R . . C2 C 0.66995(19) 0.2283(4) 0.2190(3) 0.0838(15) Uani 1 1 d . . . H2A H 0.6978 0.2269 0.2455 0.126 Uiso 1 1 calc R . . H2B H 0.6723 0.1844 0.1782 0.126 Uiso 1 1 calc R . . H2C H 0.6456 0.2060 0.2493 0.126 Uiso 1 1 calc R . . C3 C 0.57715(11) 0.5084(2) 0.22335(17) 0.0413(8) Uani 1 1 d . . . C4 C 0.53359(11) 0.5315(3) 0.25973(17) 0.0425(8) Uani 1 1 d . . . C5 C 0.50770(13) 0.4683(3) 0.29948(19) 0.0528(9) Uani 1 1 d . . . H5 H 0.5164 0.4016 0.3066 0.063 Uiso 1 1 calc R . . C6 C 0.46898(14) 0.5043(3) 0.3286(2) 0.0624(11) Uani 1 1 d . . . H6 H 0.4507 0.4619 0.3560 0.075 Uiso 1 1 calc R . . C7 C 0.45643(15) 0.6024(4) 0.3182(2) 0.0705(13) Uani 1 1 d . . . H7 H 0.4298 0.6261 0.3390 0.085 Uiso 1 1 calc R . . C8 C 0.48166(14) 0.6650(3) 0.2786(2) 0.0616(11) Uani 1 1 d . . . H8 H 0.4729 0.7316 0.2714 0.074 Uiso 1 1 calc R . . C9 C 0.52077(12) 0.6283(3) 0.24879(18) 0.0468(8) Uani 1 1 d . . . C10 C 0.55383(13) 0.6788(3) 0.20476(19) 0.0500(9) Uani 1 1 d . . . C11 C 0.61473(12) 0.4969(3) 0.27674(19) 0.0460(8) Uani 1 1 d . . . C12 C 0.61317(14) 0.5542(3) 0.3386(2) 0.0594(10) Uani 1 1 d . . . H12 H 0.5878 0.5942 0.3467 0.071 Uiso 1 1 calc R . . C13 C 0.64646(16) 0.5549(3) 0.3874(3) 0.0728(13) Uani 1 1 d . . . H13 H 0.6436 0.5950 0.4282 0.087 Uiso 1 1 calc R . . C14 C 0.68470(15) 0.4974(4) 0.3783(3) 0.0729(13) Uani 1 1 d . . . C15 C 0.68645(13) 0.4403(3) 0.3162(2) 0.0621(11) Uani 1 1 d . . . H15 H 0.7119 0.4006 0.3082 0.074 Uiso 1 1 calc R . . C16 C 0.65265(11) 0.4393(3) 0.26599(19) 0.0470(8) Uani 1 1 d . . . C17 C 0.7137(2) 0.5515(6) 0.4943(4) 0.135(3) Uani 1 1 d . . . H17A H 0.6995 0.6160 0.4849 0.161 Uiso 1 1 calc R . . H17B H 0.7439 0.5644 0.5129 0.161 Uiso 1 1 calc R . . C18 C 0.6845(3) 0.4917(9) 0.5548(4) 0.168(4) Uani 1 1 d . . . H18A H 0.6530 0.4943 0.5426 0.251 Uiso 1 1 calc R . . H18B H 0.6891 0.5228 0.6008 0.251 Uiso 1 1 calc R . . H18C H 0.6943 0.4227 0.5568 0.251 Uiso 1 1 calc R . . C19 C 0.7549(4) 0.4167(11) 0.4239(5) 0.198(5) Uani 1 1 d . . . H19A H 0.7657 0.3991 0.4714 0.238 Uiso 1 1 calc R . . H19B H 0.7444 0.3562 0.3998 0.238 Uiso 1 1 calc R . . C20 C 0.7862(4) 0.4622(12) 0.3866(7) 0.241(8) Uani 1 1 d . . . H20A H 0.7786 0.4595 0.3365 0.362 Uiso 1 1 calc R . . H20B H 0.8148 0.4293 0.3943 0.362 Uiso 1 1 calc R . . H20C H 0.7883 0.5313 0.4016 0.362 Uiso 1 1 calc R . . C21 C 0.57058(11) 0.4277(2) 0.16732(17) 0.0411(8) Uani 1 1 d . . . C22 C 0.52963(12) 0.4240(3) 0.1328(2) 0.0491(9) Uani 1 1 d . . . H22 H 0.5069 0.4680 0.1474 0.059 Uiso 1 1 calc R . . C23 C 0.52078(13) 0.3599(3) 0.0789(2) 0.0523(9) Uani 1 1 d . . . H23 H 0.4922 0.3599 0.0578 0.063 Uiso 1 1 calc R . . C24 C 0.55337(13) 0.2940(3) 0.05432(18) 0.0499(9) Uani 1 1 d . . . C25 C 0.59466(12) 0.2984(3) 0.08882(19) 0.0483(9) Uani 1 1 d . . . H25 H 0.6176 0.2555 0.0733 0.058 Uiso 1 1 calc R . . C26 C 0.60371(11) 0.3622(3) 0.14437(17) 0.0420(8) Uani 1 1 d . . . C27 C 0.50183(18) 0.2259(4) -0.0346(3) 0.0839(15) Uani 1 1 d . . . H27A H 0.5059 0.2035 -0.0837 0.101 Uiso 1 1 calc R . . H27B H 0.4892 0.2934 -0.0360 0.101 Uiso 1 1 calc R . . C28 C 0.4694(2) 0.1579(6) 0.0019(4) 0.123(2) Uani 1 1 d . . . H28A H 0.4803 0.0898 -0.0007 0.184 Uiso 1 1 calc R . . H28B H 0.4404 0.1623 -0.0212 0.184 Uiso 1 1 calc R . . H28C H 0.4664 0.1775 0.0514 0.184 Uiso 1 1 calc R . . C29 C 0.57906(18) 0.1642(4) -0.0275(3) 0.0802(14) Uani 1 1 d . . . H29A H 0.5646 0.1062 -0.0494 0.096 Uiso 1 1 calc R . . H29B H 0.5976 0.1402 0.0120 0.096 Uiso 1 1 calc R . . C30 C 0.6080(2) 0.2126(5) -0.0801(4) 0.119(2) Uani 1 1 d . . . H30A H 0.5899 0.2378 -0.1190 0.179 Uiso 1 1 calc R . . H30B H 0.6295 0.1645 -0.0984 0.179 Uiso 1 1 calc R . . H30C H 0.6240 0.2675 -0.0580 0.179 Uiso 1 1 calc R . . C31 C 0.60169(13) 0.5883(3) -0.0298(2) 0.0573(10) Uani 1 1 d . . . C32 C 0.61206(17) 0.6683(4) -0.0712(2) 0.0772(13) Uani 1 1 d . . . H32 H 0.6205 0.7292 -0.0503 0.093 Uiso 1 1 calc R . . C33 C 0.6102(2) 0.6593(5) -0.1432(3) 0.0957(18) Uani 1 1 d . . . H33 H 0.6181 0.7139 -0.1720 0.115 Uiso 1 1 calc R . . C34 C 0.59704(19) 0.5733(5) -0.1739(3) 0.0932(17) Uani 1 1 d . . . H34 H 0.5954 0.5681 -0.2236 0.112 Uiso 1 1 calc R . . C35 C 0.58625(17) 0.4943(4) -0.1321(3) 0.0831(14) Uani 1 1 d . . . H35 H 0.5773 0.4339 -0.1532 0.100 Uiso 1 1 calc R . . C36 C 0.58831(15) 0.5018(4) -0.0601(2) 0.0662(11) Uani 1 1 d . . . H36 H 0.5805 0.4470 -0.0315 0.079 Uiso 1 1 calc R . . C37 C 0.63248(14) 0.6362(3) 0.0868(2) 0.0584(10) Uani 1 1 d . . . C38 C 0.7500 0.7500 0.7215(7) 0.205(9) Uani 1 2 d SD . . Cl1 Cl 0.7212(4) 0.8430(10) 0.7567(7) 0.129(5) Uani 0.25 1 d PD . . Cl2 Cl 0.6969(3) 0.6890(12) 0.7367(7) 0.221(9) Uani 0.25 1 d PD . . Cl1' Cl 0.7662(9) 0.8712(8) 0.7252(6) 0.294(15) Uani 0.25 1 d PD . . Cl2' Cl 0.7094(3) 0.7974(8) 0.7787(5) 0.094(3) Uani 0.25 1 d PD . . N1 N 0.71750(17) 0.4961(4) 0.4276(3) 0.115(2) Uani 1 1 d . . . N2 N 0.54504(13) 0.2294(3) 0.00015(19) 0.0707(10) Uani 1 1 d . . . N3 N 0.58334(10) 0.6060(2) 0.18480(15) 0.0473(7) Uani 1 1 d . . . N4 N 0.62450(10) 0.6305(2) 0.15721(17) 0.0562(8) Uani 1 1 d . . . N5 N 0.60116(11) 0.5951(3) 0.04574(17) 0.0591(9) Uani 1 1 d . . . O1 O 0.55604(11) 0.7643(2) 0.18679(16) 0.0719(9) Uani 1 1 d . . . S1 S 0.68016(5) 0.68567(13) 0.06043(8) 0.0957(5) Uani 1 1 d . . . Si1 Si 0.65867(3) 0.35635(8) 0.18864(6) 0.0511(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.057(3) 0.146(5) 0.084(4) -0.005(4) 0.021(2) -0.005(3) C2 0.096(4) 0.072(3) 0.084(3) -0.010(3) -0.019(3) 0.028(3) C3 0.0448(18) 0.0388(17) 0.0403(18) 0.0022(15) 0.0000(14) 0.0027(14) C4 0.0492(19) 0.0424(18) 0.0360(17) -0.0046(15) -0.0021(15) 0.0016(15) C5 0.060(2) 0.051(2) 0.048(2) -0.0052(17) 0.0066(17) 0.0028(18) C6 0.062(2) 0.073(3) 0.052(2) -0.009(2) 0.0117(19) -0.004(2) C7 0.060(3) 0.082(3) 0.070(3) -0.023(3) 0.015(2) 0.011(2) C8 0.069(3) 0.056(2) 0.060(2) -0.014(2) -0.002(2) 0.019(2) C9 0.055(2) 0.0458(19) 0.0396(18) -0.0067(16) -0.0080(16) 0.0081(16) C10 0.067(2) 0.043(2) 0.0401(18) -0.0030(16) -0.0113(17) 0.0056(17) C11 0.051(2) 0.0418(19) 0.0449(19) -0.0001(16) -0.0038(16) 0.0005(16) C12 0.062(2) 0.057(2) 0.059(2) -0.011(2) -0.0132(19) 0.0079(19) C13 0.085(3) 0.063(3) 0.070(3) -0.020(2) -0.024(2) 0.008(2) C14 0.067(3) 0.072(3) 0.079(3) -0.011(3) -0.025(2) 0.004(2) C15 0.050(2) 0.062(3) 0.074(3) -0.009(2) -0.0133(19) 0.0041(19) C16 0.0426(19) 0.049(2) 0.049(2) 0.0023(17) -0.0020(15) 0.0008(15) C17 0.113(5) 0.142(6) 0.149(7) -0.078(5) -0.078(5) 0.031(5) C18 0.125(6) 0.285(13) 0.092(5) -0.030(7) -0.012(5) -0.029(8) C19 0.147(8) 0.333(17) 0.114(6) -0.047(9) -0.068(6) -0.005(11) C20 0.170(10) 0.35(2) 0.203(13) -0.126(13) 0.014(9) -0.092(12) C21 0.0449(18) 0.0380(18) 0.0405(18) 0.0002(15) 0.0015(14) 0.0007(14) C22 0.0460(19) 0.050(2) 0.052(2) -0.0087(18) -0.0001(16) 0.0068(16) C23 0.050(2) 0.057(2) 0.050(2) -0.0075(18) -0.0040(17) 0.0009(17) C24 0.062(2) 0.047(2) 0.0400(18) -0.0052(16) 0.0010(17) -0.0021(17) C25 0.055(2) 0.045(2) 0.0442(19) -0.0042(16) 0.0083(16) 0.0073(16) C26 0.0460(19) 0.0417(18) 0.0385(18) 0.0045(15) 0.0042(14) 0.0014(15) C27 0.091(3) 0.093(4) 0.067(3) -0.035(3) -0.025(3) 0.015(3) C28 0.092(4) 0.118(5) 0.157(7) -0.047(5) -0.008(4) -0.018(4) C29 0.098(4) 0.073(3) 0.070(3) -0.032(3) -0.004(3) 0.018(3) C30 0.131(5) 0.121(5) 0.106(5) -0.031(4) 0.045(4) 0.012(4) C31 0.057(2) 0.064(2) 0.050(2) 0.010(2) 0.0055(18) 0.0058(19) C32 0.095(4) 0.076(3) 0.061(3) 0.016(2) 0.002(2) -0.004(3) C33 0.116(4) 0.107(4) 0.064(3) 0.030(3) -0.001(3) -0.015(4) C34 0.095(4) 0.130(5) 0.055(3) 0.008(3) 0.002(3) -0.003(4) C35 0.086(3) 0.098(4) 0.066(3) -0.009(3) -0.005(3) -0.006(3) C36 0.072(3) 0.073(3) 0.054(2) 0.006(2) -0.003(2) -0.006(2) C37 0.057(2) 0.059(2) 0.059(2) 0.009(2) 0.0055(19) -0.0014(19) C38 0.112(9) 0.37(3) 0.130(10) 0.000 0.000 0.084(13) Cl1 0.131(9) 0.108(8) 0.149(12) -0.062(8) -0.083(8) 0.077(7) Cl2 0.110(7) 0.35(2) 0.206(13) 0.177(16) 0.012(7) -0.018(9) Cl1' 0.67(5) 0.104(7) 0.105(7) 0.010(6) 0.025(17) 0.067(17) Cl2' 0.076(4) 0.118(8) 0.088(4) -0.010(5) 0.007(3) 0.057(5) N1 0.093(3) 0.132(4) 0.120(4) -0.061(3) -0.065(3) 0.042(3) N2 0.081(2) 0.071(2) 0.060(2) -0.0245(19) -0.0062(19) 0.010(2) N3 0.0516(17) 0.0437(16) 0.0466(16) 0.0019(14) 0.0012(14) 0.0001(13) N4 0.0533(18) 0.062(2) 0.0533(19) 0.0083(16) -0.0018(15) -0.0122(15) N5 0.064(2) 0.067(2) 0.0463(18) 0.0066(17) 0.0021(15) -0.0051(17) O1 0.101(2) 0.0421(16) 0.073(2) 0.0094(14) -0.0034(17) 0.0048(15) S1 0.0681(8) 0.1293(13) 0.0899(10) 0.0178(9) 0.0131(7) -0.0300(8) Si1 0.0439(6) 0.0590(7) 0.0503(6) -0.0034(5) 0.0027(4) 0.0080(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 C1 Si1 1.856(5) . ? C2 Si1 1.859(5) . ? C3 C4 1.516(5) . ? C3 N3 1.523(4) . ? C3 C11 1.528(5) . ? C3 C21 1.539(5) . ? C4 C9 1.382(5) . ? C4 C5 1.383(5) . ? C5 C6 1.380(5) . ? C6 C7 1.396(7) . ? C7 C8 1.364(6) . ? C8 C9 1.398(5) . ? C9 C10 1.470(5) . ? C10 O1 1.209(5) . ? C10 N3 1.381(5) . ? C11 C16 1.398(5) . ? C11 C12 1.409(5) . ? C12 C13 1.367(6) . ? C13 C14 1.401(6) . ? C14 N1 1.361(6) . ? C14 C15 1.412(6) . ? C15 C16 1.395(5) . ? C16 Si1 1.859(4) . ? C17 N1 1.478(8) . ? C17 C18 1.657(12) . ? C19 C20 1.331(15) . ? C19 N1 1.559(13) . ? C21 C22 1.398(5) . ? C21 C26 1.405(5) . ? C22 C23 1.368(5) . ? C23 C24 1.407(5) . ? C24 N2 1.374(5) . ? C24 C25 1.407(5) . ? C25 C26 1.391(5) . ? C26 Si1 1.859(4) . ? C27 N2 1.460(6) . ? C27 C28 1.512(9) . ? C29 N2 1.451(6) . ? C29 C30 1.481(8) . ? C31 C36 1.366(6) . ? C31 C32 1.374(6) . ? C31 N5 1.438(5) . ? C32 C33 1.375(7) . ? C33 C34 1.360(8) . ? C34 C35 1.371(8) . ? C35 C36 1.373(7) . ? C37 N5 1.345(5) . ? C37 N4 1.361(5) . ? C37 S1 1.663(4) . ? C38 Cl1 1.669(10) 2_665 ? C38 Cl1 1.669(10) . ? C38 Cl1' 1.714(11) . ? C38 Cl1' 1.714(11) 2_665 ? C38 Cl2' 1.758(10) 2_665 ? C38 Cl2' 1.758(10) . ? C38 Cl2 1.822(9) 2_665 ? C38 Cl2 1.822(9) . ? Cl1 Cl2' 0.826(16) . ? Cl1 Cl1' 1.530(19) . ? Cl1 Cl2 2.242(16) . ? Cl2 Cl1' 1.40(2) 2_665 ? Cl2 Cl2' 1.713(18) . ? Cl1' Cl2 1.40(2) 2_665 ? Cl1' Cl2' 2.227(17) . ? N3 N4 1.387(4) . ? 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 C4 C3 N3 98.4(3) . . ? C4 C3 C11 111.1(3) . . ? N3 C3 C11 108.5(3) . . ? C4 C3 C21 110.5(3) . . ? N3 C3 C21 107.4(3) . . ? C11 C3 C21 118.8(3) . . ? C9 C4 C5 120.8(3) . . ? C9 C4 C3 111.7(3) . . ? C5 C4 C3 127.6(3) . . ? C6 C5 C4 118.5(4) . . ? C5 C6 C7 120.5(4) . . ? C8 C7 C6 121.2(4) . . ? C7 C8 C9 118.2(4) . . ? C4 C9 C8 120.8(4) . . ? C4 C9 C10 109.7(3) . . ? C8 C9 C10 129.5(4) . . ? O1 C10 N3 124.8(4) . . ? O1 C10 C9 130.1(4) . . ? N3 C10 C9 105.1(3) . . ? C16 C11 C12 117.1(3) . . ? C16 C11 C3 124.4(3) . . ? C12 C11 C3 118.2(3) . . ? C13 C12 C11 123.1(4) . . ? C12 C13 C14 121.0(4) . . ? N1 C14 C13 121.3(4) . . ? N1 C14 C15 122.7(4) . . ? C13 C14 C15 116.0(4) . . ? C16 C15 C14 123.3(4) . . ? C15 C16 C11 119.4(3) . . ? C15 C16 Si1 118.4(3) . . ? C11 C16 Si1 122.2(3) . . ? N1 C17 C18 112.9(6) . . ? C20 C19 N1 102.5(13) . . ? C22 C21 C26 117.3(3) . . ? C22 C21 C3 117.7(3) . . ? C26 C21 C3 124.9(3) . . ? C23 C22 C21 123.1(3) . . ? C22 C23 C24 121.0(3) . . ? N2 C24 C23 121.7(4) . . ? N2 C24 C25 122.5(3) . . ? C23 C24 C25 115.8(3) . . ? C26 C25 C24 123.6(3) . . ? C25 C26 C21 119.2(3) . . ? C25 C26 Si1 119.4(3) . . ? C21 C26 Si1 121.3(3) . . ? N2 C27 C28 112.9(5) . . ? N2 C29 C30 113.1(5) . . ? C36 C31 C32 120.1(4) . . ? C36 C31 N5 118.2(4) . . ? C32 C31 N5 121.5(4) . . ? C31 C32 C33 119.4(5) . . ? C34 C33 C32 120.9(5) . . ? C33 C34 C35 119.3(5) . . ? C34 C35 C36 120.5(5) . . ? C31 C36 C35 119.8(5) . . ? N5 C37 N4 115.0(3) . . ? N5 C37 S1 126.7(3) . . ? N4 C37 S1 118.1(3) . . ? Cl1 C38 Cl1 132.7(13) 2_665 . ? Cl1 C38 Cl1' 123.9(8) 2_665 . ? Cl1 C38 Cl1' 53.7(6) . . ? Cl1 C38 Cl1' 53.7(6) 2_665 2_665 ? Cl1 C38 Cl1' 123.9(8) . 2_665 ? Cl1' C38 Cl1' 175.3(13) . 2_665 ? Cl1 C38 Cl2' 27.7(6) 2_665 2_665 ? Cl1 C38 Cl2' 112.9(8) . 2_665 ? Cl1' C38 Cl2' 97.3(8) . 2_665 ? Cl1' C38 Cl2' 79.8(7) 2_665 2_665 ? Cl1 C38 Cl2' 112.9(8) 2_665 . ? Cl1 C38 Cl2' 27.7(6) . . ? Cl1' C38 Cl2' 79.8(7) . . ? Cl1' C38 Cl2' 97.3(8) 2_665 . ? Cl2' C38 Cl2' 103.6(9) 2_665 . ? Cl1 C38 Cl2 79.8(6) 2_665 2_665 ? Cl1 C38 Cl2 92.9(6) . 2_665 ? Cl1' C38 Cl2 46.4(8) . 2_665 ? Cl1' C38 Cl2 132.6(8) 2_665 2_665 ? Cl2' C38 Cl2 57.1(6) 2_665 2_665 ? Cl2' C38 Cl2 110.3(7) . 2_665 ? Cl1 C38 Cl2 92.9(6) 2_665 . ? Cl1 C38 Cl2 79.8(6) . . ? Cl1' C38 Cl2 132.6(8) . . ? Cl1' C38 Cl2 46.4(8) 2_665 . ? Cl2' C38 Cl2 110.3(7) 2_665 . ? Cl2' C38 Cl2 57.1(6) . . ? Cl2 C38 Cl2 161.8(12) 2_665 . ? Cl2' Cl1 Cl1' 140.1(14) . . ? Cl2' Cl1 C38 82.1(9) . . ? Cl1' Cl1 C38 64.6(6) . . ? Cl2' Cl1 Cl2 41.4(11) . . ? Cl1' Cl1 Cl2 117.0(6) . . ? C38 Cl1 Cl2 53.1(4) . . ? Cl1' Cl2 Cl2' 113.6(9) 2_665 . ? Cl1' Cl2 C38 62.7(7) 2_665 . ? Cl2' Cl2 C38 59.6(5) . . ? Cl1' Cl2 Cl1 108.1(8) 2_665 . ? Cl2' Cl2 Cl1 18.6(5) . . ? C38 Cl2 Cl1 47.1(4) . . ? Cl2 Cl1' Cl1 119.9(8) 2_665 . ? Cl2 Cl1' C38 70.9(6) 2_665 . ? Cl1 Cl1' C38 61.6(5) . . ? Cl2 Cl1' Cl2' 106.1(8) 2_665 . ? Cl1 Cl1' Cl2' 13.8(5) . . ? C38 Cl1' Cl2' 51.0(5) . . ? Cl1 Cl2' Cl2 119.9(14) . . ? Cl1 Cl2' C38 70.1(9) . . ? Cl2 Cl2' C38 63.3(4) . . ? Cl1 Cl2' Cl1' 26.2(10) . . ? Cl2 Cl2' Cl1' 109.9(6) . . ? C38 Cl2' Cl1' 49.2(3) . . ? C14 N1 C17 121.9(5) . . ? C14 N1 C19 120.1(5) . . ? C17 N1 C19 116.4(5) . . ? C24 N2 C29 121.9(4) . . ? C24 N2 C27 121.5(4) . . ? C29 N2 C27 116.6(4) . . ? C10 N3 N4 120.6(3) . . ? C10 N3 C3 114.1(3) . . ? N4 N3 C3 119.9(3) . . ? C37 N4 N3 122.9(3) . . ? C37 N5 C31 126.7(3) . . ? C1 Si1 C16 112.4(2) . . ? C1 Si1 C26 111.4(2) . . ? C16 Si1 C26 104.19(16) . . ? C1 Si1 C2 109.1(3) . . ? C16 Si1 C2 109.6(2) . . ? C26 Si1 C2 110.1(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.561 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.072