# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Matthias Driess' _publ_contact_author_email MATTHIAS.DRIESS@TU-BERLIN.DE _publ_section_title ; Twice Silicon-Induced C-H Activation and Tautomerisation of a ?-Diketiminato Ligand and Formation of New Types of N-Heterocyclic Silanes ; loop_ _publ_author_name 'Matthias Driess' 'Yun Xiong' 'Shenglai Yao' # Attachment 'CCDC_705079_Compound_2.cif' data_CCDC705079 _database_code_depnum_ccdc_archive 'CCDC 705079' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Br2 N2 Si' _chemical_formula_weight 492.33 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 14.9450(4) _cell_length_b 8.2720(2) _cell_length_c 17.7852(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.903(3) _cell_angle_gamma 90.00 _cell_volume 2124.73(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5635 _cell_measurement_theta_min 2.9217 _cell_measurement_theta_max 28.7107 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 3.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.358 _exptl_absorpt_correction_T_max 0.750 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13787 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3731 _reflns_number_gt 2656 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0351P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3731 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.008 _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 0.20271(6) 0.58350(11) 0.23187(5) 0.0187(2) Uani 1 1 d . . . Br1 Br 0.16249(3) 0.40161(4) 0.137393(19) 0.03375(12) Uani 1 1 d . . . Br2 Br 0.35648(2) 0.58292(5) 0.249717(19) 0.03318(12) Uani 1 1 d . . . N1 N 0.15653(17) 0.7695(3) 0.20082(13) 0.0173(6) Uani 1 1 d . . . N2 N 0.08605(18) 0.6222(3) 0.41115(14) 0.0234(7) Uani 1 1 d . . . H2 H 0.0595 0.7013 0.4282 0.035 Uiso 1 1 calc R . . C1 C 0.0838(2) 1.0298(4) 0.21802(19) 0.0320(9) Uani 1 1 d . . . H1A H 0.0558 1.0828 0.2542 0.048 Uiso 1 1 calc R . . H1B H 0.0398 1.0227 0.1682 0.048 Uiso 1 1 calc R . . H1C H 0.1367 1.0906 0.2131 0.048 Uiso 1 1 calc R . . C2 C 0.1136(2) 0.8641(4) 0.24674(17) 0.0195(7) Uani 1 1 d . . . C3 C 0.0981(2) 0.8096(4) 0.31409(17) 0.0208(7) Uani 1 1 d . . . H3 H 0.0717 0.8822 0.3421 0.031 Uiso 1 1 calc R . . C4 C 0.1185(2) 0.6504(4) 0.34668(17) 0.0187(7) Uani 1 1 d . . . C5 C 0.1674(2) 0.5378(4) 0.31757(17) 0.0221(8) Uani 1 1 d . . . H5 H 0.1820 0.4386 0.3422 0.033 Uiso 1 1 calc R . . C6 C 0.0928(2) 0.4734(4) 0.45186(18) 0.0228(8) Uani 1 1 d . . . C7 C 0.0407(2) 0.3407(4) 0.41701(19) 0.0278(8) Uani 1 1 d . . . C8 C 0.0484(3) 0.1981(4) 0.4590(2) 0.0337(9) Uani 1 1 d . . . H8 H 0.0149 0.1076 0.4368 0.051 Uiso 1 1 calc R . . C9 C 0.1057(3) 0.1890(5) 0.5337(2) 0.0380(10) Uani 1 1 d . . . H9 H 0.1111 0.0920 0.5610 0.057 Uiso 1 1 calc R . . C10 C 0.1542(2) 0.3222(5) 0.5676(2) 0.0331(9) Uani 1 1 d . . . H10 H 0.1907 0.3155 0.6185 0.050 Uiso 1 1 calc R . . C11 C 0.1500(2) 0.4662(4) 0.52754(19) 0.0251(8) Uani 1 1 d . . . C12 C -0.0247(2) 0.3541(5) 0.33694(19) 0.0355(9) Uani 1 1 d . . . H12A H 0.0103 0.3614 0.2988 0.053 Uiso 1 1 calc R . . H12B H -0.0623 0.4490 0.3344 0.053 Uiso 1 1 calc R . . H12C H -0.0638 0.2602 0.3268 0.053 Uiso 1 1 calc R . . C13 C 0.2048(2) 0.6118(5) 0.56418(19) 0.0381(10) Uani 1 1 d . . . H13A H 0.2428 0.6487 0.5316 0.057 Uiso 1 1 calc R . . H13B H 0.2433 0.5830 0.6144 0.057 Uiso 1 1 calc R . . H13C H 0.1631 0.6964 0.5699 0.057 Uiso 1 1 calc R . . C14 C 0.1533(2) 0.8242(4) 0.12225(17) 0.0213(8) Uani 1 1 d . . . C15 C 0.0755(2) 0.7843(4) 0.06265(18) 0.0265(8) Uani 1 1 d . . . C16 C 0.0758(3) 0.8263(5) -0.01299(19) 0.0389(10) Uani 1 1 d . . . H16 H 0.0259 0.7970 -0.0539 0.058 Uiso 1 1 calc R . . C17 C 0.1482(3) 0.9102(5) -0.0282(2) 0.0412(10) Uani 1 1 d . . . H17 H 0.1475 0.9354 -0.0793 0.062 Uiso 1 1 calc R . . C18 C 0.2218(3) 0.9572(4) 0.0314(2) 0.0369(10) Uani 1 1 d . . . H18 H 0.2696 1.0172 0.0204 0.055 Uiso 1 1 calc R . . C19 C 0.2258(2) 0.9162(4) 0.10811(18) 0.0255(8) Uani 1 1 d . . . C20 C -0.0085(2) 0.7015(5) 0.0777(2) 0.0373(10) Uani 1 1 d . . . H20A H -0.0297 0.6190 0.0393 0.056 Uiso 1 1 calc R . . H20B H -0.0568 0.7795 0.0747 0.056 Uiso 1 1 calc R . . H20C H 0.0077 0.6535 0.1285 0.056 Uiso 1 1 calc R . . C21 C 0.3051(2) 0.9776(4) 0.1722(2) 0.0363(9) Uani 1 1 d . . . H21A H 0.2905 0.9647 0.2214 0.055 Uiso 1 1 calc R . . H21B H 0.3153 1.0899 0.1637 0.055 Uiso 1 1 calc R . . H21C H 0.3600 0.9173 0.1724 0.055 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 Si1 0.0205(5) 0.0206(5) 0.0159(4) 0.0011(4) 0.0063(4) 0.0031(4) Br1 0.0499(3) 0.0257(2) 0.0271(2) -0.00584(17) 0.01249(17) -0.00486(19) Br2 0.0226(2) 0.0463(3) 0.0321(2) 0.00024(18) 0.00979(15) 0.00983(18) N1 0.0188(15) 0.0166(15) 0.0163(13) 0.0013(11) 0.0043(11) 0.0026(12) N2 0.0285(16) 0.0240(17) 0.0210(14) 0.0020(12) 0.0124(12) 0.0102(13) C1 0.037(2) 0.023(2) 0.040(2) 0.0071(17) 0.0178(18) 0.0087(17) C2 0.0152(17) 0.0193(19) 0.0226(17) 0.0001(14) 0.0022(14) -0.0007(14) C3 0.0221(19) 0.0205(19) 0.0204(17) -0.0025(15) 0.0066(14) 0.0055(15) C4 0.0176(18) 0.0212(19) 0.0172(17) 0.0007(14) 0.0040(14) -0.0015(14) C5 0.0242(19) 0.0233(19) 0.0206(17) 0.0067(14) 0.0091(15) 0.0042(15) C6 0.0218(19) 0.029(2) 0.0228(18) 0.0059(16) 0.0149(15) 0.0071(16) C7 0.025(2) 0.037(2) 0.0265(19) 0.0000(17) 0.0156(16) 0.0056(17) C8 0.034(2) 0.029(2) 0.046(2) 0.0014(18) 0.0247(19) 0.0003(17) C9 0.037(2) 0.037(3) 0.048(2) 0.020(2) 0.024(2) 0.0120(19) C10 0.026(2) 0.048(3) 0.029(2) 0.0166(19) 0.0130(16) 0.0093(19) C11 0.0187(18) 0.034(2) 0.0273(19) 0.0056(16) 0.0146(15) 0.0063(16) C12 0.033(2) 0.043(3) 0.033(2) -0.0087(18) 0.0129(17) -0.0054(18) C13 0.028(2) 0.058(3) 0.0268(19) 0.0049(19) 0.0045(16) -0.006(2) C14 0.0213(19) 0.0243(19) 0.0198(17) 0.0058(15) 0.0078(15) 0.0045(15) C15 0.025(2) 0.030(2) 0.0247(19) 0.0091(16) 0.0067(16) 0.0044(16) C16 0.038(2) 0.051(3) 0.023(2) 0.0118(18) 0.0008(17) 0.009(2) C17 0.047(3) 0.055(3) 0.026(2) 0.019(2) 0.0161(19) 0.010(2) C18 0.042(2) 0.037(2) 0.041(2) 0.0169(18) 0.026(2) 0.0060(19) C19 0.0234(18) 0.024(2) 0.0310(19) 0.0019(16) 0.0100(15) 0.0034(16) C20 0.024(2) 0.049(3) 0.033(2) 0.0066(19) -0.0041(16) -0.0052(18) C21 0.031(2) 0.029(2) 0.051(2) 0.0020(19) 0.0141(19) -0.0061(18) _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 N1 1.718(3) . ? Si1 C5 1.777(3) . ? Si1 Br1 2.2201(9) . ? Si1 Br2 2.2375(9) . ? N1 C2 1.401(4) . ? N1 C14 1.458(4) . ? N2 C4 1.375(4) . ? N2 C6 1.418(4) . ? C1 C2 1.490(4) . ? C2 C3 1.354(4) . ? C3 C4 1.439(4) . ? C4 C5 1.365(4) . ? C6 C7 1.396(5) . ? C6 C11 1.398(4) . ? C7 C8 1.385(5) . ? C7 C12 1.510(5) . ? C8 C9 1.385(5) . ? C9 C10 1.372(5) . ? C10 C11 1.381(5) . ? C11 C13 1.507(5) . ? C14 C15 1.396(4) . ? C14 C19 1.399(4) . ? C15 C16 1.390(4) . ? C15 C20 1.513(4) . ? C16 C17 1.370(5) . ? C17 C18 1.374(5) . ? C18 C19 1.393(4) . ? C19 C21 1.506(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 N1 Si1 C5 106.41(14) . . ? N1 Si1 Br1 110.82(9) . . ? C5 Si1 Br1 115.00(11) . . ? N1 Si1 Br2 111.14(9) . . ? C5 Si1 Br2 113.50(11) . . ? Br1 Si1 Br2 100.03(4) . . ? C2 N1 C14 118.6(2) . . ? C2 N1 Si1 121.3(2) . . ? C14 N1 Si1 119.8(2) . . ? C4 N2 C6 125.4(3) . . ? C3 C2 N1 122.5(3) . . ? C3 C2 C1 120.4(3) . . ? N1 C2 C1 117.1(3) . . ? C2 C3 C4 126.5(3) . . ? C5 C4 N2 122.5(3) . . ? C5 C4 C3 123.4(3) . . ? N2 C4 C3 114.1(3) . . ? C4 C5 Si1 119.1(2) . . ? C7 C6 C11 121.8(3) . . ? C7 C6 N2 119.8(3) . . ? C11 C6 N2 118.3(3) . . ? C8 C7 C6 118.1(3) . . ? C8 C7 C12 121.0(3) . . ? C6 C7 C12 120.9(3) . . ? C7 C8 C9 120.6(4) . . ? C10 C9 C8 120.3(3) . . ? C9 C10 C11 121.1(3) . . ? C10 C11 C6 118.0(3) . . ? C10 C11 C13 121.2(3) . . ? C6 C11 C13 120.8(3) . . ? C15 C14 C19 121.6(3) . . ? C15 C14 N1 118.1(3) . . ? C19 C14 N1 120.3(3) . . ? C16 C15 C14 117.8(3) . . ? C16 C15 C20 119.5(3) . . ? C14 C15 C20 122.6(3) . . ? C17 C16 C15 121.1(3) . . ? C16 C17 C18 120.5(3) . . ? C17 C18 C19 120.7(3) . . ? C18 C19 C14 118.0(3) . . ? C18 C19 C21 119.1(3) . . ? C14 C19 C21 122.9(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.438 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.071 # Attachment 'CCDC_705080_Compound_3.CIF' data_CCDC705080 _database_code_depnum_ccdc_archive 'CCDC 705080' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H23 Br5 N2 Si2' _chemical_formula_weight 759.14 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 11.1177(5) _cell_length_b 13.9333(7) _cell_length_c 16.9301(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2622.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4022 _cell_measurement_theta_min 3.0170 _cell_measurement_theta_max 28.4768 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.923 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 7.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.149 _exptl_absorpt_correction_T_max 0.451 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13453 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.1168 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4586 _reflns_number_gt 3015 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0221P)^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 0.005(14) _refine_ls_number_reflns 4586 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0611 _refine_ls_goodness_of_fit_ref 0.910 _refine_ls_restrained_S_all 0.910 _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 Br1 Br 0.42957(7) 0.07879(7) 0.20453(5) 0.0362(2) Uani 1 1 d . . . Br2 Br 0.60629(7) -0.09076(7) 0.29724(5) 0.0330(2) Uani 1 1 d . . . Br3 Br -0.07076(8) -0.06907(7) 0.45913(5) 0.0430(3) Uani 1 1 d . . . Br4 Br 0.07355(8) -0.27529(6) 0.52730(5) 0.0364(2) Uani 1 1 d . . . Br5 Br -0.12586(7) -0.29157(7) 0.36611(5) 0.0403(3) Uani 1 1 d . . . Si1 Si 0.42442(19) -0.02427(16) 0.30465(12) 0.0240(5) Uani 1 1 d . . . Si2 Si 0.01401(18) -0.20267(17) 0.41976(12) 0.0236(6) Uani 1 1 d . . . N1 N 0.4009(5) 0.0335(4) 0.3929(3) 0.0180(15) Uani 1 1 d . . . N2 N 0.1238(5) -0.1846(4) 0.3514(3) 0.0223(16) Uani 1 1 d . . . C1 C 0.3246(6) 0.0389(6) 0.5297(4) 0.025(2) Uani 1 1 d . . . H1A H 0.2699 0.0039 0.5648 0.038 Uiso 1 1 calc R . . H1B H 0.2996 0.1063 0.5267 0.038 Uiso 1 1 calc R . . H1C H 0.4067 0.0353 0.5506 0.038 Uiso 1 1 calc R . . C2 C 0.3210(7) -0.0046(6) 0.4493(4) 0.022(2) Uani 1 1 d . . . C3 C 0.2447(6) -0.0784(6) 0.4332(4) 0.0211(19) Uani 1 1 d . . . H3 H 0.1981 -0.1025 0.4758 0.032 Uiso 1 1 calc R . . C4 C 0.2281(6) -0.1228(6) 0.3579(4) 0.019(2) Uani 1 1 d . . . C5 C 0.3032(6) -0.1090(5) 0.2967(5) 0.0212(19) Uani 1 1 d . . . H5 H 0.2922 -0.1441 0.2492 0.032 Uiso 1 1 calc R . . C6 C 0.4515(6) 0.1299(6) 0.4087(4) 0.0183(19) Uani 1 1 d . . . C7 C 0.3807(6) 0.2098(6) 0.3890(4) 0.0193(18) Uani 1 1 d . . . C8 C 0.4285(7) 0.3001(6) 0.3999(4) 0.025(2) Uani 1 1 d . . . H8 H 0.3815 0.3552 0.3881 0.038 Uiso 1 1 calc R . . C9 C 0.5435(8) 0.3110(6) 0.4278(4) 0.031(2) Uani 1 1 d . . . H9 H 0.5767 0.3736 0.4325 0.046 Uiso 1 1 calc R . . C10 C 0.6124(7) 0.2313(6) 0.4494(4) 0.026(2) Uani 1 1 d . . . H10 H 0.6912 0.2402 0.4699 0.039 Uiso 1 1 calc R . . C11 C 0.5668(7) 0.1400(6) 0.4409(4) 0.0175(18) Uani 1 1 d . . . C12 C 0.2550(6) 0.1981(7) 0.3572(4) 0.034(2) Uani 1 1 d . . . H12A H 0.2581 0.1649 0.3062 0.051 Uiso 1 1 calc R . . H12B H 0.2181 0.2614 0.3502 0.051 Uiso 1 1 calc R . . H12C H 0.2070 0.1603 0.3944 0.051 Uiso 1 1 calc R . . C13 C 0.6384(6) 0.0565(6) 0.4720(5) 0.031(2) Uani 1 1 d . . . H13A H 0.6993 0.0381 0.4330 0.046 Uiso 1 1 calc R . . H13B H 0.5845 0.0022 0.4818 0.046 Uiso 1 1 calc R . . H13C H 0.6780 0.0750 0.5214 0.046 Uiso 1 1 calc R . . C14 C 0.1140(6) -0.2324(6) 0.2751(4) 0.0194(19) Uani 1 1 d . . . C15 C 0.0541(6) -0.1856(5) 0.2142(4) 0.0210(19) Uani 1 1 d . . . C16 C 0.0439(6) -0.2345(6) 0.1417(4) 0.028(2) Uani 1 1 d . . . H16 H 0.0028 -0.2049 0.0989 0.042 Uiso 1 1 calc R . . C17 C 0.0926(7) -0.3246(6) 0.1320(5) 0.030(2) Uani 1 1 d . . . H17 H 0.0866 -0.3560 0.0824 0.045 Uiso 1 1 calc R . . C18 C 0.1510(6) -0.3698(6) 0.1949(4) 0.025(2) Uani 1 1 d . . . H18 H 0.1814 -0.4330 0.1882 0.038 Uiso 1 1 calc R . . C19 C 0.1651(6) -0.3242(6) 0.2665(4) 0.019(2) Uani 1 1 d . . . C20 C 0.0005(7) -0.0889(6) 0.2261(4) 0.031(2) Uani 1 1 d . . . H20A H -0.0792 -0.0956 0.2502 0.047 Uiso 1 1 calc R . . H20B H -0.0071 -0.0565 0.1750 0.047 Uiso 1 1 calc R . . H20C H 0.0525 -0.0510 0.2609 0.047 Uiso 1 1 calc R . . C21 C 0.2287(7) -0.3726(6) 0.3343(4) 0.028(2) Uani 1 1 d . . . H21A H 0.1709 -0.3858 0.3766 0.041 Uiso 1 1 calc R . . H21B H 0.2923 -0.3304 0.3543 0.041 Uiso 1 1 calc R . . H21C H 0.2642 -0.4330 0.3160 0.041 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 Br1 0.0406(5) 0.0475(6) 0.0204(4) 0.0072(5) 0.0027(4) -0.0018(5) Br2 0.0317(5) 0.0400(6) 0.0273(5) -0.0022(5) 0.0048(4) 0.0030(5) Br3 0.0461(6) 0.0402(6) 0.0429(6) 0.0009(5) 0.0095(5) 0.0158(5) Br4 0.0457(6) 0.0358(6) 0.0278(5) 0.0074(4) -0.0030(4) -0.0011(5) Br5 0.0318(5) 0.0557(7) 0.0336(5) -0.0017(5) 0.0024(4) -0.0161(5) Si1 0.0272(13) 0.0293(14) 0.0154(12) -0.0051(11) 0.0002(11) -0.0075(12) Si2 0.0241(13) 0.0238(15) 0.0228(13) 0.0004(13) -0.0001(9) -0.0036(11) N1 0.019(4) 0.021(4) 0.013(3) -0.009(3) 0.004(3) 0.000(3) N2 0.030(4) 0.022(4) 0.015(3) -0.005(3) 0.000(3) -0.005(3) C1 0.029(5) 0.026(5) 0.021(5) 0.001(4) -0.001(4) -0.002(4) C2 0.031(5) 0.028(6) 0.007(4) 0.001(4) -0.002(3) 0.008(4) C3 0.018(4) 0.026(6) 0.020(4) -0.006(4) 0.005(3) -0.003(4) C4 0.017(5) 0.017(5) 0.022(5) -0.004(4) -0.009(4) 0.003(4) C5 0.031(5) 0.015(5) 0.018(4) -0.012(4) 0.002(4) -0.004(4) C6 0.014(5) 0.024(5) 0.017(4) -0.006(4) 0.002(3) 0.004(4) C7 0.014(4) 0.029(5) 0.015(4) -0.002(4) -0.001(3) 0.002(4) C8 0.031(5) 0.018(5) 0.027(5) 0.003(4) 0.004(4) 0.010(5) C9 0.043(6) 0.028(6) 0.021(5) -0.010(4) 0.015(4) -0.010(5) C10 0.029(5) 0.028(6) 0.020(4) -0.007(4) 0.006(3) -0.008(5) C11 0.012(4) 0.028(5) 0.012(4) -0.007(4) 0.003(3) 0.000(4) C12 0.034(5) 0.049(7) 0.018(5) 0.005(5) -0.010(4) 0.010(5) C13 0.014(5) 0.041(6) 0.038(5) -0.004(5) -0.002(4) 0.000(4) C14 0.019(5) 0.025(5) 0.014(4) -0.003(4) 0.002(3) -0.006(4) C15 0.019(5) 0.025(5) 0.019(5) 0.002(4) 0.001(3) -0.014(4) C16 0.015(5) 0.043(6) 0.027(5) 0.005(5) 0.003(3) 0.000(4) C17 0.036(6) 0.034(6) 0.020(5) -0.005(5) 0.011(4) -0.011(5) C18 0.024(5) 0.029(6) 0.022(5) -0.008(4) 0.003(4) 0.000(4) C19 0.015(5) 0.020(5) 0.021(5) 0.007(4) 0.006(3) 0.005(4) C20 0.045(5) 0.024(6) 0.024(5) 0.004(5) 0.005(4) 0.013(5) C21 0.026(5) 0.028(6) 0.029(5) 0.002(4) -0.004(4) 0.009(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 Br1 Si1 2.222(2) . ? Br2 Si1 2.228(2) . ? Br3 Si2 2.190(2) . ? Br4 Si2 2.186(2) . ? Br5 Si2 2.186(2) . ? Si1 N1 1.717(6) . ? Si1 C5 1.796(7) . ? Si2 N2 1.701(6) . ? N1 C2 1.410(9) . ? N1 C6 1.481(9) . ? N2 C4 1.448(8) . ? N2 C14 1.457(8) . ? C1 C2 1.491(9) . ? C2 C3 1.360(10) . ? C3 C4 1.429(9) . ? C4 C5 1.344(9) . ? C6 C11 1.400(10) . ? C6 C7 1.404(9) . ? C7 C8 1.378(10) . ? C7 C12 1.507(9) . ? C8 C9 1.371(10) . ? C9 C10 1.398(10) . ? C10 C11 1.377(9) . ? C11 C13 1.504(10) . ? C14 C15 1.390(9) . ? C14 C19 1.407(10) . ? C15 C16 1.409(9) . ? C15 C20 1.486(10) . ? C16 C17 1.377(10) . ? C17 C18 1.398(9) . ? C18 C19 1.378(9) . ? C19 C21 1.507(9) . ? 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 Si1 C5 105.0(3) . . ? N1 Si1 Br1 111.4(2) . . ? C5 Si1 Br1 112.8(3) . . ? N1 Si1 Br2 112.5(2) . . ? C5 Si1 Br2 113.8(3) . . ? Br1 Si1 Br2 101.68(9) . . ? N2 Si2 Br4 114.7(2) . . ? N2 Si2 Br5 108.2(2) . . ? Br4 Si2 Br5 107.41(10) . . ? N2 Si2 Br3 113.0(2) . . ? Br4 Si2 Br3 105.68(9) . . ? Br5 Si2 Br3 107.58(9) . . ? C2 N1 C6 117.3(6) . . ? C2 N1 Si1 120.6(5) . . ? C6 N1 Si1 121.7(5) . . ? C4 N2 C14 113.5(5) . . ? C4 N2 Si2 127.7(5) . . ? C14 N2 Si2 118.8(5) . . ? C3 C2 N1 122.8(7) . . ? C3 C2 C1 120.5(7) . . ? N1 C2 C1 116.7(7) . . ? C2 C3 C4 125.9(7) . . ? C5 C4 C3 123.0(7) . . ? C5 C4 N2 121.6(7) . . ? C3 C4 N2 115.3(6) . . ? C4 C5 Si1 120.2(6) . . ? C11 C6 C7 121.8(7) . . ? C11 C6 N1 120.6(7) . . ? C7 C6 N1 117.6(6) . . ? C8 C7 C6 118.4(7) . . ? C8 C7 C12 120.3(7) . . ? C6 C7 C12 121.3(7) . . ? C9 C8 C7 120.5(8) . . ? C8 C9 C10 120.9(8) . . ? C11 C10 C9 120.3(7) . . ? C10 C11 C6 118.1(7) . . ? C10 C11 C13 118.9(7) . . ? C6 C11 C13 122.9(7) . . ? C15 C14 C19 122.9(7) . . ? C15 C14 N2 118.6(7) . . ? C19 C14 N2 118.5(6) . . ? C14 C15 C16 117.2(7) . . ? C14 C15 C20 121.1(7) . . ? C16 C15 C20 121.6(7) . . ? C17 C16 C15 120.9(8) . . ? C16 C17 C18 120.2(8) . . ? C19 C18 C17 121.0(8) . . ? C18 C19 C14 117.7(7) . . ? C18 C19 C21 121.1(7) . . ? C14 C19 C21 121.2(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.566 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.118 # Attachment 'CCDC_705081_Compound_5.cif' data_CCDC705081 _database_code_depnum_ccdc_archive 'CCDC 705081' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Br2 N2 Si' _chemical_formula_weight 492.33 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.7680(4) _cell_length_b 7.8976(2) _cell_length_c 14.2285(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2108.98(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4973 _cell_measurement_theta_min 2.9408 _cell_measurement_theta_max 28.6145 _exptl_crystal_description drop _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 3.908 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.331 _exptl_absorpt_correction_T_max 0.509 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur S Sapphire' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11209 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3592 _reflns_number_gt 2875 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0211P)^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 0.008(8) _refine_ls_number_reflns 3592 _refine_ls_number_parameters 240 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0521 _refine_ls_wR_factor_gt 0.0482 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.015 _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 Br1 Br 0.19602(2) 0.22430(5) 0.18506(3) 0.03664(12) Uani 1 1 d . . . Br2 Br 0.07276(2) 0.25897(5) 0.00727(3) 0.03506(12) Uani 1 1 d . . . Si1 Si 0.13155(5) 0.41582(13) 0.11065(9) 0.0224(3) Uani 1 1 d . . . N1 N 0.07345(13) 0.5203(4) 0.1813(3) 0.0228(7) Uani 1 1 d . . . N2 N 0.18540(15) 0.5630(4) 0.0614(2) 0.0213(7) Uani 1 1 d . . . C1 C 0.0193(2) 0.7790(5) 0.2395(3) 0.0338(10) Uani 1 1 d . . . H1A H -0.0090 0.7157 0.2801 0.051 Uiso 1 1 calc R . . H1B H 0.0154 0.8963 0.2385 0.051 Uiso 1 1 calc R . . C2 C 0.06654(17) 0.6993(5) 0.1811(3) 0.0223(9) Uani 1 1 d . . . C3 C 0.11237(18) 0.7947(5) 0.1179(3) 0.0245(10) Uani 1 1 d . . . H3 H 0.1028 0.9100 0.1137 0.037 Uiso 1 1 calc R . . C4 C 0.16612(19) 0.7391(5) 0.0652(3) 0.0241(10) Uani 1 1 d . . . C5 C 0.2095(2) 0.8547(5) 0.0054(3) 0.0332(11) Uani 1 1 d . . . H5A H 0.1886 0.9656 0.0056 0.050 Uiso 1 1 calc R . . H5B H 0.2107 0.8120 -0.0578 0.050 Uiso 1 1 calc R . . H5C H 0.2571 0.8608 0.0297 0.050 Uiso 1 1 calc R . . C6 C 0.0262(2) 0.4237(5) 0.2412(3) 0.0257(10) Uani 1 1 d . . . C7 C -0.04105(19) 0.3771(5) 0.2082(3) 0.0260(10) Uani 1 1 d . . . C8 C -0.0815(2) 0.2648(6) 0.2622(3) 0.0418(12) Uani 1 1 d . . . H8 H -0.1249 0.2262 0.2392 0.063 Uiso 1 1 calc R . . C9 C -0.0583(2) 0.2108(6) 0.3480(4) 0.0472(13) Uani 1 1 d . . . H9 H -0.0857 0.1352 0.3827 0.071 Uiso 1 1 calc R . . C10 C 0.0058(2) 0.2688(6) 0.3832(3) 0.0422(12) Uani 1 1 d . . . H10 H 0.0200 0.2362 0.4431 0.063 Uiso 1 1 calc R . . C11 C 0.0494(2) 0.3752(5) 0.3304(3) 0.0333(11) Uani 1 1 d . . . C12 C -0.07224(19) 0.4490(5) 0.1199(3) 0.0368(12) Uani 1 1 d . . . H12A H -0.0363 0.5110 0.0865 0.055 Uiso 1 1 calc R . . H12B H -0.1109 0.5235 0.1355 0.055 Uiso 1 1 calc R . . H12C H -0.0896 0.3585 0.0810 0.055 Uiso 1 1 calc R . . C13 C 0.1176(2) 0.4418(6) 0.3733(3) 0.0495(14) Uani 1 1 d . . . H13A H 0.1513 0.4653 0.3244 0.074 Uiso 1 1 calc R . . H13B H 0.1370 0.3584 0.4152 0.074 Uiso 1 1 calc R . . H13C H 0.1077 0.5438 0.4076 0.074 Uiso 1 1 calc R . . C14 C 0.25589(18) 0.5198(4) 0.0252(3) 0.0214(10) Uani 1 1 d . . . C15 C 0.3146(2) 0.5422(5) 0.0837(3) 0.0245(10) Uani 1 1 d . . . C16 C 0.3813(2) 0.4970(5) 0.0495(3) 0.0360(11) Uani 1 1 d . . . H16 H 0.4212 0.5091 0.0877 0.054 Uiso 1 1 calc R . . C17 C 0.3893(2) 0.4345(6) -0.0404(4) 0.0384(12) Uani 1 1 d . . . H17 H 0.4342 0.4038 -0.0622 0.058 Uiso 1 1 calc R . . C18 C 0.3316(2) 0.4178(5) -0.0970(3) 0.0334(11) Uani 1 1 d . . . H18 H 0.3377 0.3766 -0.1576 0.050 Uiso 1 1 calc R . . C19 C 0.2629(2) 0.4608(5) -0.0667(3) 0.0272(10) Uani 1 1 d . . . C20 C 0.3072(2) 0.6148(5) 0.1808(3) 0.0357(10) Uani 1 1 d . . . H20A H 0.2861 0.7253 0.1769 0.054 Uiso 1 1 calc R . . H20B H 0.3534 0.6233 0.2094 0.054 Uiso 1 1 calc R . . H20C H 0.2774 0.5422 0.2180 0.054 Uiso 1 1 calc R . . C21 C 0.2017(2) 0.4444(5) -0.1336(3) 0.0377(11) Uani 1 1 d . . . H21A H 0.1884 0.3274 -0.1388 0.056 Uiso 1 1 calc R . . H21B H 0.2156 0.4863 -0.1942 0.056 Uiso 1 1 calc R . . H21C H 0.1620 0.5089 -0.1106 0.056 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 Br1 0.0356(2) 0.0278(2) 0.0466(3) 0.0049(3) -0.0050(2) 0.0058(2) Br2 0.03361(19) 0.0339(3) 0.0376(3) -0.0131(3) -0.0013(2) -0.0060(2) Si1 0.0218(5) 0.0182(6) 0.0271(7) -0.0043(6) -0.0016(5) 0.0001(5) N1 0.0213(15) 0.0248(17) 0.0223(19) -0.0012(18) -0.0008(19) -0.0007(14) N2 0.0214(17) 0.0192(18) 0.0233(19) -0.0041(14) 0.0035(15) 0.0047(15) C1 0.034(2) 0.030(2) 0.038(3) -0.004(2) 0.003(2) 0.004(2) C2 0.0214(19) 0.021(2) 0.024(2) -0.003(2) 0.006(2) 0.0023(16) C3 0.030(2) 0.016(2) 0.028(3) -0.007(2) -0.002(2) 0.0046(19) C4 0.026(2) 0.011(2) 0.035(3) -0.006(2) -0.0012(18) -0.0028(18) C5 0.032(2) 0.029(3) 0.039(3) -0.003(3) 0.008(3) 0.0018(19) C6 0.030(2) 0.024(2) 0.024(3) -0.003(2) 0.002(2) 0.001(2) C7 0.021(2) 0.029(2) 0.028(3) -0.001(2) 0.0057(18) 0.0055(18) C8 0.030(2) 0.045(3) 0.050(3) -0.008(3) 0.012(2) 0.002(3) C9 0.050(3) 0.043(3) 0.049(4) 0.008(3) 0.022(3) 0.004(3) C10 0.055(3) 0.040(3) 0.031(3) 0.001(3) 0.007(2) 0.015(3) C11 0.035(2) 0.032(3) 0.033(3) 0.004(2) 0.004(2) 0.010(2) C12 0.023(2) 0.039(3) 0.048(3) -0.007(3) 0.000(2) 0.005(2) C13 0.051(3) 0.069(4) 0.028(3) -0.002(3) -0.011(2) 0.008(3) C14 0.0214(19) 0.017(2) 0.026(3) 0.0009(18) 0.0054(19) 0.0037(17) C15 0.030(2) 0.018(2) 0.025(3) -0.0002(19) 0.001(2) 0.0012(19) C16 0.025(2) 0.042(3) 0.041(3) 0.007(3) -0.005(2) 0.003(2) C17 0.030(2) 0.041(3) 0.044(3) 0.004(3) 0.010(2) 0.012(2) C18 0.044(3) 0.034(3) 0.023(3) 0.003(2) 0.015(2) 0.009(2) C19 0.036(2) 0.022(2) 0.024(3) 0.0000(19) 0.012(2) 0.002(2) C20 0.027(2) 0.043(2) 0.037(3) -0.004(3) -0.003(2) -0.006(2) C21 0.046(3) 0.044(3) 0.023(3) 0.002(2) -0.002(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Si1 2.2074(11) . ? Br2 Si1 2.2171(12) . ? Si1 N2 1.692(3) . ? Si1 N1 1.697(3) . ? N1 C2 1.419(5) . ? N1 C6 1.448(5) . ? N2 C4 1.438(5) . ? N2 C14 1.460(4) . ? C1 C2 1.369(5) . ? C2 C3 1.455(5) . ? C3 C4 1.331(5) . ? C4 C5 1.490(6) . ? C6 C11 1.396(6) . ? C6 C7 1.396(5) . ? C7 C8 1.397(5) . ? C7 C12 1.497(5) . ? C8 C9 1.364(6) . ? C9 C10 1.381(6) . ? C10 C11 1.392(6) . ? C11 C13 1.512(5) . ? C14 C15 1.393(5) . ? C14 C19 1.394(5) . ? C15 C16 1.391(5) . ? C15 C20 1.501(5) . ? C16 C17 1.378(6) . ? C17 C18 1.356(6) . ? C18 C19 1.400(5) . ? C19 C21 1.497(5) . ? 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 Si1 N1 107.14(15) . . ? N2 Si1 Br1 110.00(11) . . ? N1 Si1 Br1 113.67(13) . . ? N2 Si1 Br2 113.98(13) . . ? N1 Si1 Br2 110.16(11) . . ? Br1 Si1 Br2 102.02(4) . . ? C2 N1 C6 118.0(3) . . ? C2 N1 Si1 122.8(3) . . ? C6 N1 Si1 119.1(2) . . ? C4 N2 C14 117.9(3) . . ? C4 N2 Si1 119.9(2) . . ? C14 N2 Si1 121.8(2) . . ? C1 C2 N1 121.1(4) . . ? C1 C2 C3 121.4(4) . . ? N1 C2 C3 117.6(3) . . ? C4 C3 C2 128.7(4) . . ? C3 C4 N2 122.1(4) . . ? C3 C4 C5 122.3(3) . . ? N2 C4 C5 115.7(3) . . ? C11 C6 C7 121.1(4) . . ? C11 C6 N1 119.3(4) . . ? C7 C6 N1 119.6(4) . . ? C6 C7 C8 118.2(4) . . ? C6 C7 C12 122.4(4) . . ? C8 C7 C12 119.3(4) . . ? C9 C8 C7 121.2(4) . . ? C8 C9 C10 119.9(4) . . ? C9 C10 C11 121.1(4) . . ? C10 C11 C6 118.2(4) . . ? C10 C11 C13 119.3(4) . . ? C6 C11 C13 122.4(4) . . ? C15 C14 C19 121.9(3) . . ? C15 C14 N2 118.4(3) . . ? C19 C14 N2 119.7(3) . . ? C16 C15 C14 118.1(4) . . ? C16 C15 C20 120.3(4) . . ? C14 C15 C20 121.7(3) . . ? C17 C16 C15 121.0(4) . . ? C18 C17 C16 120.0(4) . . ? C17 C18 C19 121.9(4) . . ? C14 C19 C18 117.2(4) . . ? C14 C19 C21 123.5(3) . . ? C18 C19 C21 119.3(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.063