# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Alan Bassindale' _publ_contact_author_email A.BASSINDALE@OPEN.AC.UK _publ_section_title ; Four independent structures of a pentacoordinate silicon species at different points on the Berry pseudorotation pathway. ; loop_ _publ_author_name 'Alan Bassindale' 'Dmitry E. Arkhipov' 'Alexander A. Korlyukov' 'M. Sohail' 'Peter G. Taylor' # Attachment '4bcd_CIF_CCDC_757286.cif' data_x2 _database_code_depnum_ccdc_archive 'CCDC 757286' #TrackingRef '4bcd_CIF_CCDC_757286.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C13 H13 Cl2 N2 O2 Si), C5 H4 Cl N O, 2(H3 O), 5(Cl)' _chemical_formula_sum 'C44 H49 Cl12 N7 O9 Si3' _chemical_formula_weight 1329.57 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.549(5) _cell_length_b 15.753(6) _cell_length_c 16.005(7) _cell_angle_alpha 67.998(8) _cell_angle_beta 74.146(9) _cell_angle_gamma 66.783(7) _cell_volume 2879(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2072 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 24.57 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8561 _exptl_absorpt_correction_T_max 0.9464 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12355 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.10 _reflns_number_total 12463 _reflns_number_gt 9987 _reflns_threshold_expression I>2u(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _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^)+(0.0930P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12463 _refine_ls_number_parameters 683 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1408 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Si1 Si 0.27519(10) 0.38816(9) 0.52956(8) 0.0189(3) Uani 1 1 d . . . Cl1 Cl 0.04844(11) 0.68726(9) 0.34403(10) 0.0401(3) Uani 1 1 d . . . Cl2 Cl 0.57900(9) 0.15630(9) 0.40000(9) 0.0318(3) Uani 1 1 d . . . O1 O 0.3540(2) 0.4702(2) 0.5072(2) 0.0236(7) Uani 1 1 d . . . O2 O 0.2060(2) 0.3115(2) 0.5208(2) 0.0202(6) Uani 1 1 d . . . N1 N 0.2179(3) 0.5784(3) 0.4284(2) 0.0220(8) Uani 1 1 d . . . N2 N 0.3749(3) 0.2348(2) 0.4610(2) 0.0178(7) Uani 1 1 d . . . C1 C 0.2405(4) 0.3656(3) 0.6538(3) 0.0269(10) Uani 1 1 d . . . H1A H 0.3017 0.3149 0.6835 0.040 Uiso 1 1 calc R . . H1B H 0.1764 0.3446 0.6759 0.040 Uiso 1 1 calc R . . H1C H 0.2249 0.4253 0.6681 0.040 Uiso 1 1 calc R . . C2 C 0.1723(4) 0.4987(3) 0.4657(3) 0.0209(9) Uani 1 1 d . . . H2A H 0.1566 0.4855 0.4157 0.025 Uiso 1 1 calc R . . H2B H 0.1037 0.5163 0.5073 0.025 Uiso 1 1 calc R . . C3 C 0.3165(4) 0.5552(3) 0.4537(3) 0.0200(9) Uani 1 1 d . . . C4 C 0.3695(4) 0.6252(3) 0.4197(3) 0.0261(10) Uani 1 1 d . . . H4A H 0.4371 0.6113 0.4372 0.031 Uiso 1 1 calc R . . C5 C 0.3221(4) 0.7133(3) 0.3610(3) 0.0313(11) Uani 1 1 d . . . H5A H 0.3577 0.7605 0.3375 0.038 Uiso 1 1 calc R . . C6 C 0.2226(4) 0.7353(3) 0.3349(3) 0.0334(11) Uani 1 1 d . . . H6A H 0.1903 0.7966 0.2940 0.040 Uiso 1 1 calc R . . C7 C 0.1730(4) 0.6666(3) 0.3696(3) 0.0279(10) Uani 1 1 d . . . C8 C 0.4061(3) 0.2970(3) 0.4905(3) 0.0199(9) Uani 1 1 d . . . H8A H 0.4507 0.3312 0.4395 0.024 Uiso 1 1 calc R . . H8B H 0.4491 0.2576 0.5413 0.024 Uiso 1 1 calc R . . C9 C 0.2657(3) 0.2498(3) 0.4771(3) 0.0188(9) Uani 1 1 d . . . C10 C 0.2249(4) 0.1989(3) 0.4471(3) 0.0222(9) Uani 1 1 d . . . H10A H 0.1493 0.2083 0.4586 0.027 Uiso 1 1 calc R . . C11 C 0.2954(4) 0.1358(3) 0.4013(3) 0.0254(10) Uani 1 1 d . . . H11A H 0.2680 0.1027 0.3789 0.030 Uiso 1 1 calc R . . C12 C 0.4081(4) 0.1187(3) 0.3864(3) 0.0237(10) Uani 1 1 d . . . H12A H 0.4573 0.0730 0.3562 0.028 Uiso 1 1 calc R . . C13 C 0.4439(3) 0.1696(3) 0.4165(3) 0.0213(9) Uani 1 1 d . . . Si1A Si 0.68331(9) 0.96448(8) 0.19449(7) 0.0136(2) Uani 1 1 d . . . Cl1A Cl 0.34809(8) 1.13088(8) 0.06605(8) 0.0229(2) Uani 1 1 d . . . Cl2A Cl 1.07093(8) 0.87703(8) 0.09439(8) 0.0226(2) Uani 1 1 d . . . O1A O 0.6596(2) 1.0911(2) 0.1900(2) 0.0169(6) Uani 1 1 d . . . O2A O 0.7092(2) 0.85026(19) 0.17061(19) 0.0160(6) Uani 1 1 d . . . N1A N 0.5123(3) 1.1215(2) 0.1301(2) 0.0147(7) Uani 1 1 d . . . N2A N 0.8811(3) 0.8532(2) 0.1332(2) 0.0157(7) Uani 1 1 d . . . C1A C 0.6624(3) 0.9136(3) 0.3203(3) 0.0191(9) Uani 1 1 d . . . H1AA H 0.5914 0.9041 0.3407 0.029 Uiso 1 1 calc R . . H1AB H 0.6652 0.9585 0.3478 0.029 Uiso 1 1 calc R . . H1AC H 0.7196 0.8512 0.3389 0.029 Uiso 1 1 calc R . . C2A C 0.5630(3) 1.0188(3) 0.1311(3) 0.0147(8) Uani 1 1 d . . . H2AA H 0.5870 1.0148 0.0680 0.018 Uiso 1 1 calc R . . H2AB H 0.5103 0.9834 0.1621 0.018 Uiso 1 1 calc R . . C3A C 0.5703(3) 1.1537(3) 0.1618(3) 0.0161(8) Uani 1 1 d . . . C4A C 0.5305(3) 1.2504(3) 0.1619(3) 0.0195(9) Uani 1 1 d . . . H4AA H 0.5696 1.2741 0.1840 0.023 Uiso 1 1 calc R . . C5A C 0.4350(3) 1.3102(3) 0.1298(3) 0.0209(9) Uani 1 1 d . . . H5AA H 0.4084 1.3760 0.1291 0.025 Uiso 1 1 calc R . . C6A C 0.3758(3) 1.2760(3) 0.0980(3) 0.0219(9) Uani 1 1 d . . . H6AA H 0.3092 1.3178 0.0760 0.026 Uiso 1 1 calc R . . C7A C 0.4157(3) 1.1815(3) 0.0993(3) 0.0173(8) Uani 1 1 d . . . C8A C 0.8313(3) 0.9495(3) 0.1466(3) 0.0163(8) Uani 1 1 d . . . H8AA H 0.8378 1.0005 0.0880 0.020 Uiso 1 1 calc R . . H8AB H 0.8678 0.9544 0.1897 0.020 Uiso 1 1 calc R . . C9A C 0.8095(3) 0.8070(3) 0.1442(3) 0.0160(8) Uani 1 1 d . . . C10A C 0.8475(3) 0.7170(3) 0.1284(3) 0.0178(8) Uani 1 1 d . . . H10B H 0.7984 0.6847 0.1347 0.021 Uiso 1 1 calc R . . C11A C 0.9566(3) 0.6761(3) 0.1037(3) 0.0209(9) Uani 1 1 d . . . H11B H 0.9830 0.6151 0.0930 0.025 Uiso 1 1 calc R . . C12A C 1.0295(3) 0.7228(3) 0.0941(3) 0.0211(9) Uani 1 1 d . . . H12B H 1.1054 0.6934 0.0789 0.025 Uiso 1 1 calc R . . C13A C 0.9888(3) 0.8118(3) 0.1072(3) 0.0182(9) Uani 1 1 d . . . Si1B Si 0.67332(9) 0.46067(8) 0.21482(8) 0.0154(2) Uani 1 1 d . . . Cl1B Cl 0.35653(8) 0.62383(8) 0.05977(7) 0.0218(2) Uani 1 1 d . . . Cl2B Cl 1.05951(8) 0.37601(8) 0.10034(7) 0.0206(2) Uani 1 1 d . . . O1B O 0.6535(2) 0.5898(2) 0.1995(2) 0.0188(6) Uani 1 1 d . . . O2B O 0.7019(2) 0.3383(2) 0.2068(2) 0.0190(6) Uani 1 1 d . . . N1B N 0.5132(3) 0.6170(2) 0.1322(2) 0.0158(7) Uani 1 1 d . . . N2B N 0.8730(3) 0.3439(2) 0.1610(2) 0.0145(7) Uani 1 1 d . . . C1B C 0.6271(4) 0.4291(3) 0.3399(3) 0.0240(10) Uani 1 1 d . . . H1BA H 0.5476 0.4544 0.3517 0.036 Uiso 1 1 calc R . . H1BB H 0.6575 0.4579 0.3672 0.036 Uiso 1 1 calc R . . H1BC H 0.6517 0.3585 0.3668 0.036 Uiso 1 1 calc R . . C2B C 0.5643(3) 0.5124(3) 0.1396(3) 0.0166(8) Uani 1 1 d . . . H2BA H 0.5966 0.5041 0.0785 0.020 Uiso 1 1 calc R . . H2BB H 0.5094 0.4789 0.1668 0.020 Uiso 1 1 calc R . . C3B C 0.5673(3) 0.6513(3) 0.1659(3) 0.0157(8) Uani 1 1 d . . . C4B C 0.5268(3) 0.7500(3) 0.1607(3) 0.0194(9) Uani 1 1 d . . . H4BA H 0.5641 0.7757 0.1824 0.023 Uiso 1 1 calc R . . C5B C 0.4345(3) 0.8081(3) 0.1248(3) 0.0226(9) Uani 1 1 d . . . H5BA H 0.4070 0.8745 0.1221 0.027 Uiso 1 1 calc R . . C6B C 0.3783(3) 0.7718(3) 0.0912(3) 0.0230(9) Uani 1 1 d . . . H6BA H 0.3135 0.8128 0.0660 0.028 Uiso 1 1 calc R . . C7B C 0.4199(3) 0.6759(3) 0.0960(3) 0.0184(9) Uani 1 1 d . . . C8B C 0.8235(3) 0.4414(3) 0.1737(3) 0.0142(8) Uani 1 1 d . . . H8BA H 0.8342 0.4917 0.1155 0.017 Uiso 1 1 calc R . . H8BB H 0.8572 0.4451 0.2193 0.017 Uiso 1 1 calc R . . C9B C 0.8016(3) 0.2949(3) 0.1800(3) 0.0170(8) Uani 1 1 d . . . C10B C 0.8404(4) 0.2015(3) 0.1704(3) 0.0198(9) Uani 1 1 d . . . H10C H 0.7926 0.1656 0.1846 0.024 Uiso 1 1 calc R . . C11B C 0.9486(3) 0.1632(3) 0.1401(3) 0.0217(9) Uani 1 1 d . . . H11C H 0.9758 0.1003 0.1330 0.026 Uiso 1 1 calc R . . C12B C 1.0192(3) 0.2152(3) 0.1195(3) 0.0200(9) Uani 1 1 d . . . H12C H 1.0942 0.1882 0.0989 0.024 Uiso 1 1 calc R . . C13B C 0.9796(3) 0.3043(3) 0.1294(3) 0.0179(8) Uani 1 1 d . . . Cl1L Cl 0.95543(10) -0.08011(9) 0.36674(9) 0.0332(3) Uani 1 1 d . . . O1L O 1.0618(2) 0.1931(2) 0.3268(2) 0.0275(7) Uani 1 1 d . . . H1LA H 1.0399 0.2547 0.3071 0.033 Uiso 1 1 d R . . N1L N 1.0039(3) 0.0694(3) 0.3531(3) 0.0223(8) Uani 1 1 d . . . C1L C 0.9852(3) 0.1531(3) 0.3692(3) 0.0217(9) Uani 1 1 d . . . C2L C 0.8938(4) 0.1914(3) 0.4262(3) 0.0271(10) Uani 1 1 d . . . H2LA H 0.8820 0.2505 0.4366 0.033 Uiso 1 1 calc R . . C3L C 0.8211(4) 0.1420(4) 0.4670(3) 0.0316(11) Uani 1 1 d . . . H3LA H 0.7583 0.1667 0.5064 0.038 Uiso 1 1 calc R . . C4L C 0.8388(4) 0.0554(4) 0.4509(3) 0.0304(11) Uani 1 1 d . . . H4LA H 0.7898 0.0197 0.4791 0.036 Uiso 1 1 calc R . . C5L C 0.9294(4) 0.0248(3) 0.3931(3) 0.0241(10) Uani 1 1 d . . . Cl3 Cl 0.34839(9) 0.44217(9) 0.29012(7) 0.0279(3) Uani 1 1 d . . . Cl3A Cl 1.20657(8) 0.01100(7) 0.06697(7) 0.0184(2) Uani 1 1 d . . . Cl3B Cl 0.20616(8) 0.51425(7) 0.04114(7) 0.0178(2) Uani 1 1 d . . . Cl4 Cl 1.38022(9) -0.07118(8) 0.32632(8) 0.0249(2) Uani 1 1 d . . . Cl5 Cl -0.00711(9) 0.38975(8) 0.34916(8) 0.0278(3) Uani 1 1 d . . . O1W O 1.1808(3) -0.0198(2) 0.2620(2) 0.0283(7) Uani 1 1 d . . . H1WA H 1.1904 -0.0021 0.2040 0.034 Uiso 1 1 d R . . H1WB H 1.2377 -0.0318 0.2831 0.034 Uiso 1 1 d R . . H1WC H 1.1227 0.0088 0.2918 0.034 Uiso 1 1 d R . . O2W O 0.1465(3) 0.4936(3) 0.2332(2) 0.0239(8) Uani 0.85 1 d P A 1 H2WA H 0.1592 0.4832 0.1821 0.029 Uiso 1 1 d R A 1 H2WB H 0.1159 0.4522 0.2683 0.029 Uiso 1 1 d R A 1 H2WC H 0.2051 0.4840 0.2506 0.029 Uiso 1 1 d R A 1 O2W' O 0.1957(17) 0.4058(16) 0.2336(15) 0.029(5) Uiso 0.15 1 d P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Si1 0.0267(6) 0.0164(6) 0.0173(6) -0.0054(5) -0.0039(5) -0.0100(5) Cl1 0.0410(7) 0.0246(6) 0.0495(8) -0.0037(6) -0.0181(6) -0.0050(6) Cl2 0.0204(5) 0.0363(7) 0.0415(7) -0.0204(6) -0.0008(5) -0.0065(5) O1 0.0315(17) 0.0193(16) 0.0255(16) -0.0065(14) -0.0074(14) -0.0120(14) O2 0.0201(15) 0.0187(15) 0.0247(16) -0.0090(13) -0.0034(12) -0.0067(12) N1 0.028(2) 0.0180(18) 0.0195(19) -0.0052(15) 0.0000(15) -0.0101(16) N2 0.0216(18) 0.0146(17) 0.0173(17) -0.0046(14) -0.0029(14) -0.0064(15) C1 0.045(3) 0.022(2) 0.020(2) -0.0060(19) -0.006(2) -0.016(2) C2 0.027(2) 0.018(2) 0.019(2) -0.0075(18) 0.0018(18) -0.0103(19) C3 0.029(2) 0.017(2) 0.017(2) -0.0073(17) -0.0018(18) -0.0090(18) C4 0.034(3) 0.028(3) 0.026(2) -0.014(2) 0.005(2) -0.020(2) C5 0.042(3) 0.025(3) 0.030(3) -0.013(2) 0.012(2) -0.022(2) C6 0.046(3) 0.016(2) 0.032(3) -0.004(2) -0.001(2) -0.011(2) C7 0.038(3) 0.022(2) 0.020(2) -0.0060(19) 0.003(2) -0.011(2) C8 0.025(2) 0.016(2) 0.025(2) -0.0055(18) -0.0086(18) -0.0103(18) C9 0.020(2) 0.019(2) 0.019(2) -0.0038(17) -0.0056(17) -0.0072(17) C10 0.025(2) 0.019(2) 0.023(2) -0.0044(18) -0.0039(18) -0.0085(19) C11 0.037(3) 0.022(2) 0.023(2) -0.0062(19) -0.004(2) -0.016(2) C12 0.028(2) 0.019(2) 0.026(2) -0.0129(19) 0.0010(19) -0.0087(19) C13 0.019(2) 0.020(2) 0.024(2) -0.0061(18) -0.0038(18) -0.0056(18) Si1A 0.0114(5) 0.0106(5) 0.0184(5) -0.0042(4) -0.0026(4) -0.0031(4) Cl1A 0.0155(5) 0.0208(5) 0.0365(6) -0.0108(5) -0.0099(4) -0.0042(4) Cl2A 0.0124(5) 0.0220(5) 0.0344(6) -0.0102(5) -0.0012(4) -0.0066(4) O1A 0.0126(14) 0.0125(14) 0.0248(15) -0.0053(12) -0.0065(12) -0.0012(12) O2A 0.0102(13) 0.0121(14) 0.0255(15) -0.0089(12) -0.0005(11) -0.0020(11) N1A 0.0130(16) 0.0128(17) 0.0201(17) -0.0055(14) -0.0032(14) -0.0051(13) N2A 0.0148(17) 0.0164(18) 0.0159(16) -0.0047(14) -0.0032(14) -0.0049(14) C1A 0.019(2) 0.018(2) 0.019(2) -0.0041(17) -0.0026(17) -0.0060(17) C2A 0.0144(19) 0.0107(19) 0.020(2) -0.0050(16) -0.0034(16) -0.0047(16) C3A 0.014(2) 0.014(2) 0.019(2) -0.0028(17) -0.0037(16) -0.0045(16) C4A 0.020(2) 0.017(2) 0.024(2) -0.0062(18) -0.0062(18) -0.0066(18) C5A 0.017(2) 0.014(2) 0.032(2) -0.0090(18) -0.0048(18) -0.0028(17) C6A 0.015(2) 0.018(2) 0.032(2) -0.0072(19) -0.0052(19) -0.0047(17) C7A 0.0141(19) 0.020(2) 0.020(2) -0.0073(18) -0.0030(16) -0.0065(17) C8A 0.0138(19) 0.012(2) 0.023(2) -0.0062(17) -0.0027(17) -0.0035(16) C9A 0.020(2) 0.016(2) 0.0115(19) -0.0019(16) -0.0064(16) -0.0048(17) C10A 0.022(2) 0.016(2) 0.018(2) -0.0059(17) -0.0033(17) -0.0073(17) C11A 0.022(2) 0.014(2) 0.026(2) -0.0056(18) -0.0055(18) -0.0037(18) C12A 0.0129(19) 0.020(2) 0.027(2) -0.0073(19) -0.0015(17) -0.0023(17) C13A 0.015(2) 0.022(2) 0.017(2) -0.0062(17) -0.0002(16) -0.0071(18) Si1B 0.0129(5) 0.0141(6) 0.0212(6) -0.0073(5) -0.0033(5) -0.0039(4) Cl1B 0.0174(5) 0.0231(6) 0.0286(5) -0.0077(4) -0.0084(4) -0.0073(4) Cl2B 0.0135(5) 0.0216(5) 0.0296(5) -0.0107(4) -0.0004(4) -0.0077(4) O1B 0.0151(14) 0.0162(15) 0.0278(16) -0.0090(13) -0.0078(12) -0.0023(12) O2B 0.0137(14) 0.0151(15) 0.0309(17) -0.0100(13) -0.0045(12) -0.0036(12) N1B 0.0141(16) 0.0135(17) 0.0218(18) -0.0078(14) -0.0023(14) -0.0044(14) N2B 0.0128(16) 0.0078(16) 0.0220(18) -0.0051(14) -0.0050(14) -0.0004(13) C1B 0.027(2) 0.025(2) 0.023(2) -0.0096(19) -0.0018(19) -0.011(2) C2B 0.0095(18) 0.015(2) 0.026(2) -0.0112(17) -0.0020(16) -0.0013(16) C3B 0.016(2) 0.016(2) 0.0158(19) -0.0053(16) -0.0015(16) -0.0050(17) C4B 0.015(2) 0.016(2) 0.029(2) -0.0090(18) -0.0026(17) -0.0057(17) C5B 0.019(2) 0.014(2) 0.032(2) -0.0083(19) -0.0010(19) -0.0029(18) C6B 0.019(2) 0.019(2) 0.029(2) -0.0064(19) -0.0046(19) -0.0031(18) C7B 0.016(2) 0.023(2) 0.019(2) -0.0053(18) -0.0013(17) -0.0107(18) C8B 0.0121(19) 0.0100(19) 0.021(2) -0.0059(16) -0.0058(16) -0.0005(16) C9B 0.014(2) 0.018(2) 0.022(2) -0.0085(17) -0.0050(16) -0.0045(17) C10B 0.020(2) 0.015(2) 0.026(2) -0.0082(18) -0.0025(18) -0.0068(18) C11B 0.019(2) 0.016(2) 0.031(2) -0.0094(19) -0.0063(19) -0.0024(18) C12B 0.016(2) 0.019(2) 0.023(2) -0.0065(18) -0.0028(17) -0.0027(18) C13B 0.014(2) 0.018(2) 0.021(2) -0.0043(17) -0.0034(17) -0.0058(17) Cl1L 0.0307(6) 0.0296(6) 0.0426(7) -0.0138(6) -0.0013(5) -0.0133(5) O1L 0.0239(16) 0.0305(18) 0.0319(18) -0.0127(15) -0.0012(14) -0.0116(14) N1L 0.0159(18) 0.025(2) 0.028(2) -0.0096(16) -0.0056(15) -0.0050(16) C1L 0.018(2) 0.031(2) 0.019(2) -0.0081(19) -0.0052(17) -0.0085(19) C2L 0.026(2) 0.028(3) 0.027(2) -0.014(2) -0.0029(19) -0.003(2) C3L 0.022(2) 0.038(3) 0.029(3) -0.012(2) 0.001(2) -0.007(2) C4L 0.022(2) 0.033(3) 0.030(3) -0.002(2) 0.000(2) -0.012(2) C5L 0.021(2) 0.024(2) 0.028(2) -0.008(2) -0.0066(19) -0.0051(19) Cl3 0.0244(6) 0.0402(7) 0.0199(5) -0.0092(5) -0.0013(4) -0.0124(5) Cl3A 0.0161(5) 0.0170(5) 0.0249(5) -0.0095(4) -0.0040(4) -0.0046(4) Cl3B 0.0154(5) 0.0162(5) 0.0218(5) -0.0072(4) -0.0033(4) -0.0033(4) Cl4 0.0215(5) 0.0271(6) 0.0309(6) -0.0123(5) -0.0003(4) -0.0119(5) Cl5 0.0262(6) 0.0297(6) 0.0282(6) -0.0107(5) -0.0037(5) -0.0083(5) O1W 0.0230(17) 0.036(2) 0.0252(17) -0.0114(15) -0.0011(13) -0.0083(15) O2W 0.0233(19) 0.031(2) 0.0201(18) -0.0092(16) -0.0026(15) -0.0109(16) _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 C1 1.842(4) . ? Si1 O2 1.858(3) . ? Si1 O1 1.864(3) . ? Si1 C2 1.885(5) . ? Si1 C8 1.913(5) . ? Cl1 C7 1.722(5) . ? Cl2 C13 1.714(4) . ? O1 C3 1.276(5) . ? O2 C9 1.291(5) . ? N1 C7 1.360(6) . ? N1 C3 1.371(6) . ? N1 C2 1.471(5) . ? N2 C13 1.365(5) . ? N2 C9 1.368(5) . ? N2 C8 1.465(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.410(6) . ? C4 C5 1.368(7) . ? C4 H4A 0.9500 . ? C5 C6 1.393(7) . ? C5 H5A 0.9500 . ? C6 C7 1.360(6) . ? C6 H6A 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.399(6) . ? C10 C11 1.361(6) . ? C10 H10A 0.9500 . ? C11 C12 1.410(6) . ? C11 H11A 0.9500 . ? C12 C13 1.355(6) . ? C12 H12A 0.9500 . ? Si1A C1A 1.853(4) . ? Si1A O2A 1.858(3) . ? Si1A O1A 1.866(3) . ? Si1A C2A 1.890(4) . ? Si1A C8A 1.894(4) . ? Cl1A C7A 1.708(4) . ? Cl2A C13A 1.719(4) . ? O1A C3A 1.289(5) . ? O2A C9A 1.289(5) . ? N1A C3A 1.363(5) . ? N1A C7A 1.370(5) . ? N1A C2A 1.483(5) . ? N2A C13A 1.360(5) . ? N2A C9A 1.368(5) . ? N2A C8A 1.470(5) . ? C1A H1AA 0.9800 . ? C1A H1AB 0.9800 . ? C1A H1AC 0.9800 . ? C2A H2AA 0.9900 . ? C2A H2AB 0.9900 . ? C3A C4A 1.402(6) . ? C4A C5A 1.366(6) . ? C4A H4AA 0.9500 . ? C5A C6A 1.402(6) . ? C5A H5AA 0.9500 . ? C6A C7A 1.363(6) . ? C6A H6AA 0.9500 . ? C8A H8AA 0.9900 . ? C8A H8AB 0.9900 . ? C9A C10A 1.400(6) . ? C10A C11A 1.370(6) . ? C10A H10B 0.9500 . ? C11A C12A 1.394(6) . ? C11A H11B 0.9500 . ? C12A C13A 1.365(6) . ? C12A H12B 0.9500 . ? Si1B O2B 1.859(3) . ? Si1B C1B 1.861(4) . ? Si1B O1B 1.871(3) . ? Si1B C2B 1.893(4) . ? Si1B C8B 1.896(4) . ? Cl1B C7B 1.713(4) . ? Cl2B C13B 1.720(4) . ? O1B C3B 1.285(5) . ? O2B C9B 1.285(5) . ? N1B C3B 1.365(5) . ? N1B C7B 1.367(5) . ? N1B C2B 1.486(5) . ? N2B C13B 1.363(5) . ? N2B C9B 1.369(5) . ? N2B C8B 1.483(5) . ? C1B H1BA 0.9800 . ? C1B H1BB 0.9800 . ? C1B H1BC 0.9800 . ? C2B H2BA 0.9900 . ? C2B H2BB 0.9900 . ? C3B C4B 1.409(6) . ? C4B C5B 1.352(6) . ? C4B H4BA 0.9500 . ? C5B C6B 1.411(6) . ? C5B H5BA 0.9500 . ? C6B C7B 1.368(6) . ? C6B H6BA 0.9500 . ? C8B H8BA 0.9900 . ? C8B H8BB 0.9900 . ? C9B C10B 1.408(6) . ? C10B C11B 1.372(6) . ? C10B H10C 0.9500 . ? C11B C12B 1.393(6) . ? C11B H11C 0.9500 . ? C12B C13B 1.345(6) . ? C12B H12C 0.9500 . ? Cl1L C5L 1.736(5) . ? O1L C1L 1.320(5) . ? O1L H1LA 0.8515 . ? N1L C5L 1.339(6) . ? N1L C1L 1.350(6) . ? C1L C2L 1.392(6) . ? C2L C3L 1.368(7) . ? C2L H2LA 0.9500 . ? C3L C4L 1.398(7) . ? C3L H3LA 0.9500 . ? C4L C5L 1.357(6) . ? C4L H4LA 0.9500 . ? O1W H1WA 0.8503 . ? O1W H1WB 0.8515 . ? O1W H1WC 0.8523 . ? O2W H2WA 0.8515 . ? O2W H2WB 0.8505 . ? O2W H2WC 0.8518 . ? O2W' H2WA 1.1856 . ? O2W' H2WB 1.1676 . ? O2W' H2WC 1.4160 . ? 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 C1 Si1 O2 97.17(17) . . ? C1 Si1 O1 97.11(17) . . ? O2 Si1 O1 165.72(15) . . ? C1 Si1 C2 112.3(2) . . ? O2 Si1 C2 89.11(17) . . ? O1 Si1 C2 85.77(17) . . ? C1 Si1 C8 115.0(2) . . ? O2 Si1 C8 85.18(16) . . ? O1 Si1 C8 88.51(16) . . ? C2 Si1 C8 132.67(19) . . ? C3 O1 Si1 115.0(3) . . ? C9 O2 Si1 114.7(3) . . ? C7 N1 C3 120.7(4) . . ? C7 N1 C2 125.2(4) . . ? C3 N1 C2 114.0(4) . . ? C13 N2 C9 120.0(3) . . ? C13 N2 C8 125.5(4) . . ? C9 N2 C8 114.4(3) . . ? Si1 C1 H1A 109.5 . . ? Si1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Si1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 Si1 107.9(3) . . ? N1 C2 H2A 110.1 . . ? Si1 C2 H2A 110.1 . . ? N1 C2 H2B 110.1 . . ? Si1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? O1 C3 N1 116.7(4) . . ? O1 C3 C4 124.3(4) . . ? N1 C3 C4 119.0(4) . . ? C5 C4 C3 118.9(5) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C4 C5 C6 121.5(4) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C7 C6 C5 118.2(5) . . ? C7 C6 H6A 120.9 . . ? C5 C6 H6A 120.9 . . ? C6 C7 N1 121.8(5) . . ? C6 C7 Cl1 122.0(4) . . ? N1 C7 Cl1 116.2(3) . . ? N2 C8 Si1 107.3(3) . . ? N2 C8 H8A 110.2 . . ? Si1 C8 H8A 110.2 . . ? N2 C8 H8B 110.2 . . ? Si1 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? O2 C9 N2 116.2(3) . . ? O2 C9 C10 123.9(4) . . ? N2 C9 C10 119.9(4) . . ? C11 C10 C9 118.9(4) . . ? C11 C10 H10A 120.6 . . ? C9 C10 H10A 120.6 . . ? C10 C11 C12 121.3(4) . . ? C10 C11 H11A 119.4 . . ? C12 C11 H11A 119.4 . . ? C13 C12 C11 117.8(4) . . ? C13 C12 H12A 121.1 . . ? C11 C12 H12A 121.1 . . ? C12 C13 N2 122.1(4) . . ? C12 C13 Cl2 121.7(4) . . ? N2 C13 Cl2 116.1(3) . . ? C1A Si1A O2A 95.93(17) . . ? C1A Si1A O1A 96.99(17) . . ? O2A Si1A O1A 167.04(14) . . ? C1A Si1A C2A 119.33(19) . . ? O2A Si1A C2A 86.99(15) . . ? O1A Si1A C2A 85.84(15) . . ? C1A Si1A C8A 111.98(19) . . ? O2A Si1A C8A 86.21(15) . . ? O1A Si1A C8A 89.86(15) . . ? C2A Si1A C8A 128.66(19) . . ? C3A O1A Si1A 114.9(3) . . ? C9A O2A Si1A 114.9(3) . . ? C3A N1A C7A 121.3(3) . . ? C3A N1A C2A 114.6(3) . . ? C7A N1A C2A 124.1(3) . . ? C13A N2A C9A 120.1(4) . . ? C13A N2A C8A 124.9(3) . . ? C9A N2A C8A 115.0(3) . . ? Si1A C1A H1AA 109.5 . . ? Si1A C1A H1AB 109.5 . . ? H1AA C1A H1AB 109.5 . . ? Si1A C1A H1AC 109.5 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? N1A C2A Si1A 107.1(2) . . ? N1A C2A H2AA 110.3 . . ? Si1A C2A H2AA 110.3 . . ? N1A C2A H2AB 110.3 . . ? Si1A C2A H2AB 110.3 . . ? H2AA C2A H2AB 108.5 . . ? O1A C3A N1A 116.3(4) . . ? O1A C3A C4A 124.6(4) . . ? N1A C3A C4A 119.1(4) . . ? C5A C4A C3A 119.3(4) . . ? C5A C4A H4AA 120.3 . . ? C3A C4A H4AA 120.3 . . ? C4A C5A C6A 121.0(4) . . ? C4A C5A H5AA 119.5 . . ? C6A C5A H5AA 119.5 . . ? C7A C6A C5A 118.6(4) . . ? C7A C6A H6AA 120.7 . . ? C5A C6A H6AA 120.7 . . ? C6A C7A N1A 120.7(4) . . ? C6A C7A Cl1A 122.6(3) . . ? N1A C7A Cl1A 116.6(3) . . ? N2A C8A Si1A 106.8(3) . . ? N2A C8A H8AA 110.4 . . ? Si1A C8A H8AA 110.4 . . ? N2A C8A H8AB 110.4 . . ? Si1A C8A H8AB 110.4 . . ? H8AA C8A H8AB 108.6 . . ? O2A C9A N2A 116.1(4) . . ? O2A C9A C10A 124.1(4) . . ? N2A C9A C10A 119.7(4) . . ? C11A C10A C9A 119.0(4) . . ? C11A C10A H10B 120.5 . . ? C9A C10A H10B 120.5 . . ? C10A C11A C12A 121.1(4) . . ? C10A C11A H11B 119.5 . . ? C12A C11A H11B 119.5 . . ? C13A C12A C11A 118.1(4) . . ? C13A C12A H12B 121.0 . . ? C11A C12A H12B 121.0 . . ? N2A C13A C12A 122.0(4) . . ? N2A C13A Cl2A 116.0(3) . . ? C12A C13A Cl2A 122.0(3) . . ? O2B Si1B C1B 95.48(17) . . ? O2B Si1B O1B 169.30(15) . . ? C1B Si1B O1B 95.21(17) . . ? O2B Si1B C2B 89.76(15) . . ? C1B Si1B C2B 116.4(2) . . ? O1B Si1B C2B 85.57(15) . . ? O2B Si1B C8B 86.54(15) . . ? C1B Si1B C8B 117.77(19) . . ? O1B Si1B C8B 88.39(15) . . ? C2B Si1B C8B 125.77(19) . . ? C3B O1B Si1B 114.4(2) . . ? C9B O2B Si1B 115.1(3) . . ? C3B N1B C7B 121.3(4) . . ? C3B N1B C2B 114.2(3) . . ? C7B N1B C2B 124.5(3) . . ? C13B N2B C9B 120.4(3) . . ? C13B N2B C8B 124.9(3) . . ? C9B N2B C8B 114.7(3) . . ? Si1B C1B H1BA 109.5 . . ? Si1B C1B H1BB 109.5 . . ? H1BA C1B H1BB 109.5 . . ? Si1B C1B H1BC 109.5 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? N1B C2B Si1B 106.9(3) . . ? N1B C2B H2BA 110.3 . . ? Si1B C2B H2BA 110.3 . . ? N1B C2B H2BB 110.3 . . ? Si1B C2B H2BB 110.3 . . ? H2BA C2B H2BB 108.6 . . ? O1B C3B N1B 116.6(4) . . ? O1B C3B C4B 124.6(4) . . ? N1B C3B C4B 118.8(4) . . ? C5B C4B C3B 119.7(4) . . ? C5B C4B H4BA 120.1 . . ? C3B C4B H4BA 120.1 . . ? C4B C5B C6B 121.1(4) . . ? C4B C5B H5BA 119.4 . . ? C6B C5B H5BA 119.4 . . ? C7B C6B C5B 118.1(4) . . ? C7B C6B H6BA 121.0 . . ? C5B C6B H6BA 121.0 . . ? N1B C7B C6B 121.0(4) . . ? N1B C7B Cl1B 117.1(3) . . ? C6B C7B Cl1B 121.9(3) . . ? N2B C8B Si1B 107.0(2) . . ? N2B C8B H8BA 110.3 . . ? Si1B C8B H8BA 110.3 . . ? N2B C8B H8BB 110.3 . . ? Si1B C8B H8BB 110.3 . . ? H8BA C8B H8BB 108.6 . . ? O2B C9B N2B 116.7(4) . . ? O2B C9B C10B 124.1(4) . . ? N2B C9B C10B 119.3(4) . . ? C11B C10B C9B 118.7(4) . . ? C11B C10B H10C 120.6 . . ? C9B C10B H10C 120.6 . . ? C10B C11B C12B 120.9(4) . . ? C10B C11B H11C 119.6 . . ? C12B C11B H11C 119.6 . . ? C13B C12B C11B 118.9(4) . . ? C13B C12B H12C 120.5 . . ? C11B C12B H12C 120.5 . . ? C12B C13B N2B 121.7(4) . . ? C12B C13B Cl2B 122.0(3) . . ? N2B C13B Cl2B 116.2(3) . . ? C1L O1L H1LA 115.5 . . ? C5L N1L C1L 117.3(4) . . ? O1L C1L N1L 113.6(4) . . ? O1L C1L C2L 124.3(4) . . ? N1L C1L C2L 122.1(4) . . ? C3L C2L C1L 118.4(4) . . ? C3L C2L H2LA 120.8 . . ? C1L C2L H2LA 120.8 . . ? C2L C3L C4L 120.3(4) . . ? C2L C3L H3LA 119.8 . . ? C4L C3L H3LA 119.8 . . ? C5L C4L C3L 116.9(4) . . ? C5L C4L H4LA 121.6 . . ? C3L C4L H4LA 121.6 . . ? N1L C5L C4L 125.0(4) . . ? N1L C5L Cl1L 115.2(3) . . ? C4L C5L Cl1L 119.9(4) . . ? H1WA O1W H1WB 112.2 . . ? H1WA O1W H1WC 121.0 . . ? H1WB O1W H1WC 113.0 . . ? H2WA O2W H2WB 102.6 . . ? H2WA O2W H2WC 111.2 . . ? H2WB O2W H2WC 111.3 . . ? H2WA O2W' H2WB 68.7 . . ? H2WA O2W' H2WC 64.7 . . ? H2WB O2W' H2WC 65.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Si1 O1 C3 -119.8(3) . . . . ? O2 Si1 O1 C3 61.5(7) . . . . ? C2 Si1 O1 C3 -7.8(3) . . . . ? C8 Si1 O1 C3 125.1(3) . . . . ? C1 Si1 O2 C9 -128.6(3) . . . . ? O1 Si1 O2 C9 50.2(7) . . . . ? C2 Si1 O2 C9 119.1(3) . . . . ? C8 Si1 O2 C9 -13.9(3) . . . . ? C7 N1 C2 Si1 172.1(3) . . . . ? C3 N1 C2 Si1 -4.1(4) . . . . ? C1 Si1 C2 N1 102.1(3) . . . . ? O2 Si1 C2 N1 -160.5(3) . . . . ? O1 Si1 C2 N1 6.1(3) . . . . ? C8 Si1 C2 N1 -77.9(4) . . . . ? Si1 O1 C3 N1 7.3(5) . . . . ? Si1 O1 C3 C4 -172.7(3) . . . . ? C7 N1 C3 O1 -178.3(4) . . . . ? C2 N1 C3 O1 -1.9(5) . . . . ? C7 N1 C3 C4 1.6(6) . . . . ? C2 N1 C3 C4 178.1(4) . . . . ? O1 C3 C4 C5 178.6(4) . . . . ? N1 C3 C4 C5 -1.4(6) . . . . ? C3 C4 C5 C6 0.5(7) . . . . ? C4 C5 C6 C7 0.2(7) . . . . ? C5 C6 C7 N1 0.1(7) . . . . ? C5 C6 C7 Cl1 178.4(4) . . . . ? C3 N1 C7 C6 -1.0(7) . . . . ? C2 N1 C7 C6 -177.0(4) . . . . ? C3 N1 C7 Cl1 -179.4(3) . . . . ? C2 N1 C7 Cl1 4.5(6) . . . . ? C13 N2 C8 Si1 170.2(3) . . . . ? C9 N2 C8 Si1 -6.4(4) . . . . ? C1 Si1 C8 N2 106.1(3) . . . . ? O2 Si1 C8 N2 10.5(3) . . . . ? O1 Si1 C8 N2 -156.7(3) . . . . ? C2 Si1 C8 N2 -73.9(4) . . . . ? Si1 O2 C9 N2 13.6(5) . . . . ? Si1 O2 C9 C10 -166.9(3) . . . . ? C13 N2 C9 O2 178.9(4) . . . . ? C8 N2 C9 O2 -4.2(5) . . . . ? C13 N2 C9 C10 -0.6(6) . . . . ? C8 N2 C9 C10 176.3(4) . . . . ? O2 C9 C10 C11 179.8(4) . . . . ? N2 C9 C10 C11 -0.8(6) . . . . ? C9 C10 C11 C12 2.2(7) . . . . ? C10 C11 C12 C13 -2.2(7) . . . . ? C11 C12 C13 N2 0.8(7) . . . . ? C11 C12 C13 Cl2 -178.7(3) . . . . ? C9 N2 C13 C12 0.5(6) . . . . ? C8 N2 C13 C12 -175.9(4) . . . . ? C9 N2 C13 Cl2 -179.9(3) . . . . ? C8 N2 C13 Cl2 3.6(6) . . . . ? C1A Si1A O1A C3A -109.3(3) . . . . ? O2A Si1A O1A C3A 66.4(7) . . . . ? C2A Si1A O1A C3A 9.8(3) . . . . ? C8A Si1A O1A C3A 138.6(3) . . . . ? C1A Si1A O2A C9A -104.7(3) . . . . ? O1A Si1A O2A C9A 79.6(7) . . . . ? C2A Si1A O2A C9A 136.1(3) . . . . ? C8A Si1A O2A C9A 7.0(3) . . . . ? C3A N1A C2A Si1A 8.5(4) . . . . ? C7A N1A C2A Si1A -172.3(3) . . . . ? C1A Si1A C2A N1A 86.3(3) . . . . ? O2A Si1A C2A N1A -178.6(3) . . . . ? O1A Si1A C2A N1A -9.4(3) . . . . ? C8A Si1A C2A N1A -95.9(3) . . . . ? Si1A O1A C3A N1A -7.0(5) . . . . ? Si1A O1A C3A C4A 173.1(3) . . . . ? C7A N1A C3A O1A 179.4(4) . . . . ? C2A N1A C3A O1A -1.4(5) . . . . ? C7A N1A C3A C4A -0.6(6) . . . . ? C2A N1A C3A C4A 178.6(4) . . . . ? O1A C3A C4A C5A 179.6(4) . . . . ? N1A C3A C4A C5A -0.3(6) . . . . ? C3A C4A C5A C6A 0.8(7) . . . . ? C4A C5A C6A C7A -0.3(7) . . . . ? C5A C6A C7A N1A -0.7(6) . . . . ? C5A C6A C7A Cl1A 177.6(3) . . . . ? C3A N1A C7A C6A 1.1(6) . . . . ? C2A N1A C7A C6A -178.0(4) . . . . ? C3A N1A C7A Cl1A -177.2(3) . . . . ? C2A N1A C7A Cl1A 3.6(5) . . . . ? C13A N2A C8A Si1A -174.1(3) . . . . ? C9A N2A C8A Si1A 9.3(4) . . . . ? C1A Si1A C8A N2A 86.4(3) . . . . ? O2A Si1A C8A N2A -8.5(3) . . . . ? O1A Si1A C8A N2A -176.1(3) . . . . ? C2A Si1A C8A N2A -91.6(3) . . . . ? Si1A O2A C9A N2A -3.0(4) . . . . ? Si1A O2A C9A C10A 175.6(3) . . . . ? C13A N2A C9A O2A 178.7(3) . . . . ? C8A N2A C9A O2A -4.5(5) . . . . ? C13A N2A C9A C10A 0.0(6) . . . . ? C8A N2A C9A C10A 176.7(4) . . . . ? O2A C9A C10A C11A -177.5(4) . . . . ? N2A C9A C10A C11A 1.1(6) . . . . ? C9A C10A C11A C12A -0.1(6) . . . . ? C10A C11A C12A C13A -2.0(7) . . . . ? C9A N2A C13A C12A -2.2(6) . . . . ? C8A N2A C13A C12A -178.6(4) . . . . ? C9A N2A C13A Cl2A 179.3(3) . . . . ? C8A N2A C13A Cl2A 2.9(5) . . . . ? C11A C12A C13A N2A 3.2(6) . . . . ? C11A C12A C13A Cl2A -178.4(3) . . . . ? O2B Si1B O1B C3B 78.1(8) . . . . ? C1B Si1B O1B C3B -102.4(3) . . . . ? C2B Si1B O1B C3B 13.8(3) . . . . ? C8B Si1B O1B C3B 139.8(3) . . . . ? C1B Si1B O2B C9B -117.2(3) . . . . ? O1B Si1B O2B C9B 62.3(8) . . . . ? C2B Si1B O2B C9B 126.3(3) . . . . ? C8B Si1B O2B C9B 0.4(3) . . . . ? C3B N1B C2B Si1B 10.6(4) . . . . ? C7B N1B C2B Si1B -168.9(3) . . . . ? O2B Si1B C2B N1B 177.1(3) . . . . ? C1B Si1B C2B N1B 81.1(3) . . . . ? O1B Si1B C2B N1B -12.5(3) . . . . ? C8B Si1B C2B N1B -97.3(3) . . . . ? Si1B O1B C3B N1B -10.7(5) . . . . ? Si1B O1B C3B C4B 170.2(3) . . . . ? C7B N1B C3B O1B 179.2(4) . . . . ? C2B N1B C3B O1B -0.4(5) . . . . ? C7B N1B C3B C4B -1.6(6) . . . . ? C2B N1B C3B C4B 178.8(4) . . . . ? O1B C3B C4B C5B -179.3(4) . . . . ? N1B C3B C4B C5B 1.5(6) . . . . ? C3B C4B C5B C6B -0.7(7) . . . . ? C4B C5B C6B C7B 0.0(7) . . . . ? C3B N1B C7B C6B 0.9(6) . . . . ? C2B N1B C7B C6B -179.6(4) . . . . ? C3B N1B C7B Cl1B -177.6(3) . . . . ? C2B N1B C7B Cl1B 1.9(5) . . . . ? C5B C6B C7B N1B 0.0(6) . . . . ? C5B C6B C7B Cl1B 178.4(3) . . . . ? C13B N2B C8B Si1B 178.1(3) . . . . ? C9B N2B C8B Si1B 0.7(4) . . . . ? O2B Si1B C8B N2B -0.6(3) . . . . ? C1B Si1B C8B N2B 93.8(3) . . . . ? O1B Si1B C8B N2B -171.1(3) . . . . ? C2B Si1B C8B N2B -87.8(3) . . . . ? Si1B O2B C9B N2B -0.1(5) . . . . ? Si1B O2B C9B C10B 179.2(3) . . . . ? C13B N2B C9B O2B -178.0(4) . . . . ? C8B N2B C9B O2B -0.4(5) . . . . ? C13B N2B C9B C10B 2.7(6) . . . . ? C8B N2B C9B C10B -179.8(4) . . . . ? O2B C9B C10B C11B 179.2(4) . . . . ? N2B C9B C10B C11B -1.5(6) . . . . ? C9B C10B C11B C12B 0.3(7) . . . . ? C10B C11B C12B C13B -0.3(7) . . . . ? C11B C12B C13B N2B 1.5(6) . . . . ? C11B C12B C13B Cl2B -176.7(3) . . . . ? C9B N2B C13B C12B -2.8(6) . . . . ? C8B N2B C13B C12B 180.0(4) . . . . ? C9B N2B C13B Cl2B 175.6(3) . . . . ? C8B N2B C13B Cl2B -1.7(5) . . . . ? C5L N1L C1L O1L -179.4(4) . . . . ? C5L N1L C1L C2L 1.2(6) . . . . ? O1L C1L C2L C3L -179.2(4) . . . . ? N1L C1L C2L C3L 0.1(7) . . . . ? C1L C2L C3L C4L -0.4(7) . . . . ? C2L C3L C4L C5L -0.7(7) . . . . ? C1L N1L C5L C4L -2.5(7) . . . . ? C1L N1L C5L Cl1L 177.8(3) . . . . ? C3L C4L C5L N1L 2.3(7) . . . . ? C3L C4L C5L Cl1L -178.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1W H1WA Cl3A 0.85 2.08 2.916(3) 166 . yes O1W H1WB Cl4 0.85 2.01 2.861(5) 174 . yes O1W H1WC N1L 0.85 1.76 2.611(6) 179 . yes O2W H2WA Cl3B 0.85 2.09 2.883(3) 154 . yes O2W H2WB Cl5 0.85 2.14 2.958(4) 161 . yes O2W H2WC Cl3 0.85 1.99 2.834(5) 172 . yes _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.002 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.105 _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _vrf_PLAT772_x2 ; PROBLEM: Suspect O-H Bond in CIF: O2W' -- H2WC .. 1.42 Ang. RESPONSE: The O2W atom is disordered over two postions with non-equivalent occupancies (4:1). This "contact is simply distance between second position with least occupancy with hydrogen atom attached to the fist position with largest occupacy". The location of hydrogen atoms positions for O2W'is impossible. ; _vrf_REFLT01_x2 ; PROBLEM: The number of symmetry-independent reflections cannot exceed the total number of reflections measured Number of symmetry-independent reflections = 12463 Total number of reflections = 12355 RESPONSE: The studied crystal was twin. The twinning was treated using CELL_NOW and TWINABS programs. The procedure implemented in TWINABS caused to the merging of all equivalent reflections but further refinement with separate scaling factors for two twin components (HKLF 5 and BASF instructions) caused noticeable descease of R1 and residual electron density values (from 0.11 to 0.05). Also, the absence of some reflections can be explained by low symmetry of crystal (triclinic). ; # Attachment '4bcd_CIF_CCDC_7572861.cif' # Attachment '4a_CIF_CCDC_757287.CIF' data_sm108bis _database_code_depnum_ccdc_archive 'CCDC 757287' #TrackingRef '4a_CIF_CCDC_7572871.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 Cl2 N2 O2 Si, C5 H4 Cl N O, H2 O, Cl ' _chemical_formula_sum 'C18 H19 Cl4 N3 O4 Si' _chemical_formula_weight 511.25 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6414(8) _cell_length_b 21.915(2) _cell_length_c 12.8697(14) _cell_angle_alpha 90.00 _cell_angle_beta 96.267(2) _cell_angle_gamma 90.00 _cell_volume 2142.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6205 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 32.95 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.640 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8826 _exptl_absorpt_correction_T_max 0.9271 _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26805 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.03 _reflns_number_total 6212 _reflns_number_gt 5481 _reflns_threshold_expression I>2u(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998)' _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^)+(0.0464P)^2^+1.8647P] 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 6212 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 Si1 Si 0.27339(5) 0.934801(19) 0.63217(3) 0.01380(9) Uani 1 1 d . . . Cl1 Cl 0.36258(5) 1.065262(18) 0.93857(3) 0.01892(9) Uani 1 1 d . . . O1 O 0.04453(14) 0.94269(5) 0.66396(9) 0.0166(2) Uani 1 1 d . . . N1 N 0.17421(16) 1.00228(6) 0.79343(10) 0.0137(2) Uani 1 1 d . . . C1 C 0.33803(19) 0.98360(7) 0.75156(12) 0.0150(3) Uani 1 1 d . . . H1A H 0.4135 0.9600 0.8047 0.018 Uiso 1 1 calc R . . H1B H 0.4043 1.0200 0.7323 0.018 Uiso 1 1 calc R . . C2 C 0.0242(2) 0.97821(7) 0.74167(12) 0.0143(3) Uani 1 1 d . . . C3 C -0.1401(2) 0.99299(8) 0.77466(13) 0.0179(3) Uani 1 1 d . . . H3A H -0.2455 0.9765 0.7398 0.022 Uiso 1 1 calc R . . C4 C -0.1457(2) 1.03161(8) 0.85802(13) 0.0200(3) Uani 1 1 d . . . H4A H -0.2561 1.0423 0.8803 0.024 Uiso 1 1 calc R . . C5 C 0.0093(2) 1.05549(8) 0.91088(13) 0.0187(3) Uani 1 1 d . . . H5A H 0.0051 1.0821 0.9688 0.022 Uiso 1 1 calc R . . C6 C 0.1664(2) 1.03962(7) 0.87729(12) 0.0154(3) Uani 1 1 d . . . Cl1' Cl 0.26929(6) 0.712547(18) 0.63227(3) 0.02376(10) Uani 1 1 d . . . O1' O 0.51176(15) 0.91793(5) 0.62357(9) 0.0172(2) Uani 1 1 d . . . N1' N 0.41512(17) 0.82053(6) 0.62160(10) 0.0147(2) Uani 1 1 d . . . C1' C 0.2464(2) 0.84898(7) 0.63942(12) 0.0161(3) Uani 1 1 d . . . H1'A H 0.2135 0.8372 0.7090 0.019 Uiso 1 1 calc R . . H1'B H 0.1523 0.8352 0.5856 0.019 Uiso 1 1 calc R . . C2' C 0.5490(2) 0.86110(7) 0.61220(12) 0.0153(3) Uani 1 1 d . . . C3' C 0.7141(2) 0.83947(8) 0.59094(13) 0.0194(3) Uani 1 1 d . . . H3'A H 0.8070 0.8671 0.5816 0.023 Uiso 1 1 calc R . . C4' C 0.7388(2) 0.77756(9) 0.58386(13) 0.0232(3) Uani 1 1 d . . . H4'A H 0.8502 0.7624 0.5697 0.028 Uiso 1 1 calc R . . C5' C 0.6029(2) 0.73629(8) 0.59716(13) 0.0221(3) Uani 1 1 d . . . H5'A H 0.6215 0.6935 0.5932 0.027 Uiso 1 1 calc R . . C6' C 0.4433(2) 0.75911(7) 0.61585(12) 0.0178(3) Uani 1 1 d . . . C100 C 0.2363(2) 0.97394(8) 0.50452(13) 0.0215(3) Uani 1 1 d . . . H10A H 0.1975 1.0159 0.5149 0.032 Uiso 1 1 calc R . . H10B H 0.1455 0.9522 0.4592 0.032 Uiso 1 1 calc R . . H10C H 0.3461 0.9745 0.4717 0.032 Uiso 1 1 calc R . . Cl1L Cl 0.94704(6) 0.63377(2) 0.82234(5) 0.03402(12) Uani 1 1 d . . . O1L O 0.44065(17) 0.75655(6) 0.88170(11) 0.0263(3) Uani 1 1 d . . . H1LA H 0.4007 0.7918 0.8931 0.039 Uiso 1 1 d R . . N1L N 0.68567(19) 0.70504(7) 0.85498(11) 0.0206(3) Uani 1 1 d . . . C1L C 0.6108(2) 0.75926(8) 0.86597(12) 0.0192(3) Uani 1 1 d . . . C2L C 0.7015(2) 0.81463(8) 0.86177(13) 0.0202(3) Uani 1 1 d . . . H2LA H 0.6435 0.8525 0.8686 0.024 Uiso 1 1 calc R . . C3L C 0.8778(2) 0.81228(8) 0.84731(13) 0.0214(3) Uani 1 1 d . . . H3LA H 0.9436 0.8490 0.8456 0.026 Uiso 1 1 calc R . . C4L C 0.9594(2) 0.75639(8) 0.83530(13) 0.0212(3) Uani 1 1 d . . . H4LA H 1.0804 0.7536 0.8250 0.025 Uiso 1 1 calc R . . C5L C 0.8550(2) 0.70538(8) 0.83913(13) 0.0198(3) Uani 1 1 d . . . Cl2 Cl 0.28980(5) 0.874779(18) 0.93522(3) 0.01925(9) Uani 1 1 d . . . O1W O 0.4043(2) 0.61108(7) 0.85779(13) 0.0366(3) Uani 1 1 d . . . H1WA H 0.4863 0.6372 0.8568 0.055 Uiso 1 1 d R . . H1WB H 0.3268 0.6384 0.8627 0.055 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 0.01094(18) 0.01396(19) 0.01672(19) -0.00061(14) 0.00245(14) 0.00010(14) Cl1 0.01574(17) 0.01843(17) 0.02190(18) -0.00486(13) -0.00112(13) 0.00093(13) O1 0.0111(5) 0.0196(5) 0.0192(5) -0.0038(4) 0.0021(4) -0.0007(4) N1 0.0119(5) 0.0128(5) 0.0163(6) -0.0001(4) 0.0014(4) 0.0010(4) C1 0.0103(6) 0.0152(6) 0.0201(7) -0.0017(5) 0.0043(5) -0.0008(5) C2 0.0126(6) 0.0140(6) 0.0165(6) 0.0007(5) 0.0022(5) 0.0002(5) C3 0.0109(6) 0.0220(7) 0.0212(7) 0.0004(6) 0.0030(5) 0.0007(5) C4 0.0150(7) 0.0232(8) 0.0225(8) 0.0016(6) 0.0052(6) 0.0047(6) C5 0.0191(7) 0.0186(7) 0.0189(7) -0.0019(6) 0.0037(6) 0.0038(6) C6 0.0147(6) 0.0138(6) 0.0173(7) -0.0001(5) 0.0001(5) 0.0013(5) Cl1' 0.0315(2) 0.01485(17) 0.0251(2) -0.00269(14) 0.00382(16) -0.00341(14) O1' 0.0121(5) 0.0161(5) 0.0238(6) -0.0007(4) 0.0040(4) 0.0004(4) N1' 0.0142(6) 0.0155(6) 0.0144(6) -0.0012(4) 0.0022(4) 0.0015(5) C1' 0.0124(6) 0.0157(7) 0.0206(7) -0.0011(5) 0.0042(5) 0.0003(5) C2' 0.0136(6) 0.0189(7) 0.0134(6) 0.0004(5) 0.0011(5) 0.0012(5) C3' 0.0147(7) 0.0256(8) 0.0180(7) -0.0013(6) 0.0024(5) 0.0031(6) C4' 0.0203(8) 0.0303(9) 0.0191(7) -0.0040(6) 0.0024(6) 0.0106(7) C5' 0.0279(8) 0.0206(8) 0.0172(7) -0.0037(6) -0.0008(6) 0.0089(6) C6' 0.0239(8) 0.0158(7) 0.0135(7) -0.0016(5) 0.0008(6) 0.0020(6) C100 0.0182(7) 0.0260(8) 0.0205(7) 0.0046(6) 0.0030(6) 0.0030(6) Cl1L 0.0263(2) 0.0246(2) 0.0515(3) -0.00566(19) 0.0052(2) 0.00474(17) O1L 0.0181(6) 0.0253(6) 0.0369(7) -0.0085(5) 0.0097(5) -0.0035(5) N1L 0.0190(6) 0.0216(7) 0.0214(7) -0.0026(5) 0.0028(5) -0.0025(5) C1L 0.0174(7) 0.0250(8) 0.0155(7) -0.0042(6) 0.0035(5) -0.0019(6) C2L 0.0201(7) 0.0226(8) 0.0181(7) -0.0025(6) 0.0033(6) -0.0020(6) C3L 0.0208(8) 0.0226(8) 0.0209(7) 0.0001(6) 0.0024(6) -0.0051(6) C4L 0.0158(7) 0.0287(9) 0.0188(7) -0.0003(6) 0.0014(6) -0.0015(6) C5L 0.0201(7) 0.0214(8) 0.0180(7) -0.0014(6) 0.0020(6) 0.0014(6) Cl2 0.01533(16) 0.02018(18) 0.02291(18) -0.00098(13) 0.00506(13) -0.00158(13) O1W 0.0305(7) 0.0276(7) 0.0519(10) 0.0011(6) 0.0055(7) 0.0018(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 Si1 O1 1.8471(12) . ? Si1 C100 1.8475(17) . ? Si1 O1' 1.8737(12) . ? Si1 C1 1.8928(16) . ? Si1 C1' 1.8955(16) . ? Cl1 C6 1.7106(16) . ? O1 C2 1.2901(19) . ? N1 C6 1.361(2) . ? N1 C2 1.3669(19) . ? N1 C1 1.4738(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.407(2) . ? C3 C4 1.371(2) . ? C3 H3A 0.9500 . ? C4 C5 1.401(2) . ? C4 H4A 0.9500 . ? C5 C6 1.365(2) . ? C5 H5A 0.9500 . ? Cl1' C6' 1.7073(18) . ? O1' C2' 1.2893(19) . ? N1' C6' 1.366(2) . ? N1' C2' 1.370(2) . ? N1' C1' 1.4725(19) . ? C1' H1'A 0.9900 . ? C1' H1'B 0.9900 . ? C2' C3' 1.403(2) . ? C3' C4' 1.374(3) . ? C3' H3'A 0.9500 . ? C4' C5' 1.401(3) . ? C4' H4'A 0.9500 . ? C5' C6' 1.364(2) . ? C5' H5'A 0.9500 . ? C100 H10A 0.9800 . ? C100 H10B 0.9800 . ? C100 H10C 0.9800 . ? Cl1L C5L 1.7427(18) . ? O1L C1L 1.339(2) . ? O1L H1LA 0.8500 . ? N1L C5L 1.332(2) . ? N1L C1L 1.333(2) . ? C1L C2L 1.401(2) . ? C2L C3L 1.381(2) . ? C2L H2LA 0.9500 . ? C3L C4L 1.391(3) . ? C3L H3LA 0.9500 . ? C4L C5L 1.377(2) . ? C4L H4LA 0.9500 . ? O1W H1WA 0.8504 . ? O1W H1WB 0.8499 . ? 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 O1 Si1 C100 95.53(7) . . ? O1 Si1 O1' 168.98(6) . . ? C100 Si1 O1' 95.45(7) . . ? O1 Si1 C1 86.38(6) . . ? C100 Si1 C1 117.42(8) . . ? O1' Si1 C1 89.44(6) . . ? O1 Si1 C1' 88.35(6) . . ? C100 Si1 C1' 119.84(8) . . ? O1' Si1 C1' 85.34(6) . . ? C1 Si1 C1' 122.74(7) . . ? C2 O1 Si1 115.15(10) . . ? C6 N1 C2 120.77(13) . . ? C6 N1 C1 124.70(13) . . ? C2 N1 C1 114.52(12) . . ? N1 C1 Si1 107.27(10) . . ? N1 C1 H1A 110.3 . . ? Si1 C1 H1A 110.3 . . ? N1 C1 H1B 110.3 . . ? Si1 C1 H1B 110.3 . . ? H1A C1 H1B 108.5 . . ? O1 C2 N1 116.44(13) . . ? O1 C2 C3 124.04(14) . . ? N1 C2 C3 119.52(14) . . ? C4 C3 C2 118.89(15) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C3 C4 C5 120.93(15) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 118.50(15) . . ? C6 C5 H5A 120.8 . . ? C4 C5 H5A 120.8 . . ? N1 C6 C5 121.36(14) . . ? N1 C6 Cl1 116.82(11) . . ? C5 C6 Cl1 121.81(13) . . ? C2' O1' Si1 115.16(10) . . ? C6' N1' C2' 120.73(14) . . ? C6' N1' C1' 124.84(13) . . ? C2' N1' C1' 114.42(13) . . ? N1' C1' Si1 108.10(10) . . ? N1' C1' H1'A 110.1 . . ? Si1 C1' H1'A 110.1 . . ? N1' C1' H1'B 110.1 . . ? Si1 C1' H1'B 110.1 . . ? H1'A C1' H1'B 108.4 . . ? O1' C2' N1' 116.16(13) . . ? O1' C2' C3' 124.24(15) . . ? N1' C2' C3' 119.60(15) . . ? C4' C3' C2' 118.64(16) . . ? C4' C3' H3'A 120.7 . . ? C2' C3' H3'A 120.7 . . ? C3' C4' C5' 121.35(16) . . ? C3' C4' H4'A 119.3 . . ? C5' C4' H4'A 119.3 . . ? C6' C5' C4' 118.28(16) . . ? C6' C5' H5'A 120.9 . . ? C4' C5' H5'A 120.9 . . ? C5' C6' N1' 121.33(16) . . ? C5' C6' Cl1' 121.76(13) . . ? N1' C6' Cl1' 116.91(12) . . ? Si1 C100 H10A 109.5 . . ? Si1 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? Si1 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? C1L O1L H1LA 111.0 . . ? C5L N1L C1L 116.53(15) . . ? N1L C1L O1L 114.30(15) . . ? N1L C1L C2L 123.25(15) . . ? O1L C1L C2L 122.46(16) . . ? C3L C2L C1L 117.81(16) . . ? C3L C2L H2LA 121.1 . . ? C1L C2L H2LA 121.1 . . ? C2L C3L C4L 120.25(16) . . ? C2L C3L H3LA 119.9 . . ? C4L C3L H3LA 119.9 . . ? C5L C4L C3L 116.25(15) . . ? C5L C4L H4LA 121.9 . . ? C3L C4L H4LA 121.9 . . ? N1L C5L C4L 125.89(16) . . ? N1L C5L Cl1L 115.22(13) . . ? C4L C5L Cl1L 118.89(13) . . ? H1WA O1W H1WB 92.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C100 Si1 O1 C2 -112.75(12) . . . . ? O1' Si1 O1 C2 72.4(3) . . . . ? C1 Si1 O1 C2 4.48(12) . . . . ? C1' Si1 O1 C2 127.43(12) . . . . ? C6 N1 C1 Si1 -177.60(12) . . . . ? C2 N1 C1 Si1 3.24(15) . . . . ? O1 Si1 C1 N1 -3.99(10) . . . . ? C100 Si1 C1 N1 90.36(11) . . . . ? O1' Si1 C1 N1 -173.79(10) . . . . ? C1' Si1 C1 N1 -89.69(12) . . . . ? Si1 O1 C2 N1 -3.60(17) . . . . ? Si1 O1 C2 C3 176.33(12) . . . . ? C6 N1 C2 O1 -179.13(14) . . . . ? C1 N1 C2 O1 0.06(19) . . . . ? C6 N1 C2 C3 0.9(2) . . . . ? C1 N1 C2 C3 -179.88(14) . . . . ? O1 C2 C3 C4 -179.60(15) . . . . ? N1 C2 C3 C4 0.3(2) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C2 N1 C6 C5 -1.6(2) . . . . ? C1 N1 C6 C5 179.25(15) . . . . ? C2 N1 C6 Cl1 178.06(11) . . . . ? C1 N1 C6 Cl1 -1.1(2) . . . . ? C4 C5 C6 N1 1.0(2) . . . . ? C4 C5 C6 Cl1 -178.65(13) . . . . ? O1 Si1 O1' C2' 64.0(3) . . . . ? C100 Si1 O1' C2' -110.91(12) . . . . ? C1 Si1 O1' C2' 131.59(12) . . . . ? C1' Si1 O1' C2' 8.67(12) . . . . ? C6' N1' C1' Si1 -176.52(12) . . . . ? C2' N1' C1' Si1 4.42(15) . . . . ? O1 Si1 C1' N1' -177.66(10) . . . . ? C100 Si1 C1' N1' 86.91(12) . . . . ? O1' Si1 C1' N1' -6.70(10) . . . . ? C1 Si1 C1' N1' -93.03(11) . . . . ? Si1 O1' C2' N1' -8.18(17) . . . . ? Si1 O1' C2' C3' 171.55(12) . . . . ? C6' N1' C2' O1' -176.86(14) . . . . ? C1' N1' C2' O1' 2.25(19) . . . . ? C6' N1' C2' C3' 3.4(2) . . . . ? C1' N1' C2' C3' -177.49(14) . . . . ? O1' C2' C3' C4' 177.94(15) . . . . ? N1' C2' C3' C4' -2.3(2) . . . . ? C2' C3' C4' C5' 0.2(3) . . . . ? C3' C4' C5' C6' 1.0(3) . . . . ? C4' C5' C6' N1' 0.0(2) . . . . ? C4' C5' C6' Cl1' 179.57(13) . . . . ? C2' N1' C6' C5' -2.2(2) . . . . ? C1' N1' C6' C5' 178.75(15) . . . . ? C2' N1' C6' Cl1' 178.19(11) . . . . ? C1' N1' C6' Cl1' -0.8(2) . . . . ? C5L N1L C1L O1L 179.99(14) . . . . ? C5L N1L C1L C2L -0.1(2) . . . . ? N1L C1L C2L C3L -1.2(2) . . . . ? O1L C1L C2L C3L 178.69(15) . . . . ? C1L C2L C3L C4L 1.3(2) . . . . ? C2L C3L C4L C5L -0.2(2) . . . . ? C1L N1L C5L C4L 1.4(3) . . . . ? C1L N1L C5L Cl1L -178.68(12) . . . . ? C3L C4L C5L N1L -1.2(3) . . . . ? C3L C4L C5L Cl1L 178.86(13) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.615 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.071 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1L H1LA Cl2 0.85 2.10 2.9478(14) 174 . yes O1W H1WA N1L 0.85 2.13 2.980(2) 178 . yes _publ_section_references ; Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465, East Cheryl Parkway, Madison, WI 5317. Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ; _vrf_PLAT420_sm108bis ; PROBLEM: D-H Without Acceptor O1W - H1WB RESPONSE: The H1WB atom participates in weak H-bond with Cl1L atom d(H..A) 2.893,