# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/352 data_global _publ_contact_author 'A.J. Blake' _publ_contact_author_email A.J.Blake@Nottingham.ac.uk loop_ _publ_author_name 'A. Ariffin' 'A.J. Blake' 'M.R. Ebden' 'W-S. Li' 'N.S. Simpkins' _publ_section_title ; The diastereoselective and enantioselective substitution reactions of an isoindiline-borane complex ; _journal_name_full 'JCS Perkin 1' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '1999' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------- #4 Chemical and physical data # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag include any ASCII file output by a chemical drawing # package # Against _type record, for example, ChemDraw # Against _records supply the chemical connectivity records data_Compound_4i # BZNMBH _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 B N' _chemical_formula_weight 161.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.061(3) _cell_length_b 9.145(3) _cell_length_c 11.597(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.76(3) _cell_angle_gamma 90.00 _cell_volume 968.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 17.0 _exptl_crystal_description sphenoid _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-2.2' _diffrn_reflns_number 2221 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1698 _reflns_number_gt 1425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement 'STADI4 (Stoe & Cie, 1997a)' _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _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 w=1/[\s^2^(Fo^2^)+(0.035P)^2^+0.48P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'calculated (C-H); found from difference map (B-H)' _refine_ls_hydrogen_treatment 'riding model (C-H); rigid group (B-H)' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1698 _refine_ls_number_parameters 119 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.132 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.55574(17) 0.08722(17) 0.84015(15) 0.0234(4) Uani 1 d . . . H1 H 0.6071 0.0032 0.8964 0.028 Uiso 1 calc R . . C1' C 0.50972(19) 0.0386(2) 0.70502(16) 0.0337(4) Uani 1 d . . . H1'A H 0.4434 -0.0452 0.6875 0.051 Uiso 1 calc R . . H1'B H 0.5964 0.0102 0.6920 0.051 Uiso 1 calc R . . H1'C H 0.4594 0.1191 0.6475 0.051 Uiso 1 calc R . . N2 N 0.65979(14) 0.21770(14) 0.87981(12) 0.0219(3) Uani 1 d . . . B B 0.6105(2) 0.3496(2) 0.77586(18) 0.0284(4) Uani 1 d D . . H1B H 0.6840(17) 0.4440(18) 0.8279(16) 0.043 Uiso 1 d D . . H2B H 0.4908(16) 0.376(2) 0.7511(17) 0.043 Uiso 1 d D . . H3B H 0.6297(18) 0.314(2) 0.6914(15) 0.043 Uiso 1 d D . . C2' C 0.81152(17) 0.1716(2) 0.90673(16) 0.0303(4) Uani 1 d . . . H2'A H 0.8412 0.0923 0.9693 0.045 Uiso 1 calc R . . H2'B H 0.8780 0.2548 0.9405 0.045 Uiso 1 calc R . . H2'C H 0.8154 0.1374 0.8281 0.045 Uiso 1 calc R . . C3 C 0.64983(17) 0.27029(18) 0.99921(15) 0.0240(4) Uani 1 d . . . H3A H 0.7163 0.2142 1.0743 0.029 Uiso 1 calc R . . H3B H 0.6737 0.3756 1.0137 0.029 Uiso 1 calc R . . C4 C 0.49278(17) 0.24230(17) 0.97202(14) 0.0229(4) Uani 1 d . . . C5 C 0.40664(18) 0.30470(18) 1.02562(15) 0.0272(4) Uani 1 d . . . H5 H 0.4456 0.3760 1.0908 0.033 Uiso 1 calc R . . C6 C 0.26165(19) 0.26016(19) 0.98144(16) 0.0307(4) Uani 1 d . . . H6 H 0.2008 0.3011 1.0174 0.037 Uiso 1 calc R . . C7 C 0.20453(18) 0.15682(19) 0.88567(16) 0.0304(4) Uani 1 d . . . H7 H 0.1048 0.1287 0.8559 0.036 Uiso 1 calc R . . C8 C 0.29223(17) 0.09383(18) 0.83263(15) 0.0264(4) Uani 1 d . . . H7 H 0.2535 0.0227 0.7673 0.032 Uiso 1 calc R . . C9 C 0.43666(17) 0.13728(17) 0.87732(14) 0.0221(4) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0237(8) 0.0191(8) 0.0265(8) -0.0005(6) 0.0096(7) 0.0001(6) C1' 0.0296(9) 0.0352(10) 0.0355(10) -0.0112(8) 0.0129(8) -0.0018(8) N2 0.0208(7) 0.0211(7) 0.0243(7) -0.0013(5) 0.0099(6) -0.0004(5) B 0.0346(11) 0.0261(10) 0.0288(10) 0.0036(8) 0.0175(9) 0.0010(8) C2' 0.0225(8) 0.0334(10) 0.0348(10) -0.0036(8) 0.0119(7) 0.0004(7) C3 0.0266(8) 0.0236(8) 0.0216(8) -0.0013(7) 0.0097(7) -0.0001(7) C4 0.0266(8) 0.0209(8) 0.0215(8) 0.0044(6) 0.0103(7) 0.0028(6) C5 0.0340(9) 0.0254(9) 0.0246(9) 0.0031(7) 0.0145(7) 0.0053(7) C6 0.0318(9) 0.0337(10) 0.0327(9) 0.0092(8) 0.0196(8) 0.0107(7) C7 0.0228(8) 0.0336(10) 0.0349(10) 0.0110(8) 0.0124(7) 0.0035(7) C8 0.0255(8) 0.0248(9) 0.0263(8) 0.0031(7) 0.0080(7) -0.0006(7) C9 0.0250(8) 0.0195(8) 0.0219(8) 0.0051(6) 0.0099(6) 0.0024(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 C1 C1' 1.503(2) . ? C1 C9 1.504(2) . ? C1 N2 1.526(2) . ? N2 C2' 1.485(2) . ? N2 C3 1.508(2) . ? N2 B 1.629(2) . ? C3 C4 1.498(2) . ? C4 C5 1.384(2) . ? C4 C9 1.388(2) . ? C5 C6 1.389(2) . ? C6 C7 1.386(3) . ? C7 C8 1.394(2) . ? C8 C9 1.381(2) . ? 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' C1 C9 117.01(14) . . ? C1' C1 N2 114.73(13) . . ? C9 C1 N2 101.76(12) . . ? C2' N2 C3 110.80(12) . . ? C2' N2 C1 110.88(12) . . ? C3 N2 C1 103.01(11) . . ? C2' N2 B 109.47(13) . . ? C3 N2 B 109.06(12) . . ? C1 N2 B 113.47(12) . . ? C4 C3 N2 102.83(12) . . ? C5 C4 C9 121.12(15) . . ? C5 C4 C3 129.71(15) . . ? C9 C4 C3 109.17(13) . . ? C4 C5 C6 118.16(16) . . ? C7 C6 C5 120.94(15) . . ? C6 C7 C8 120.57(16) . . ? C9 C8 C7 118.45(16) . . ? C8 C9 C4 120.75(15) . . ? C8 C9 C1 130.08(15) . . ? C4 C9 C1 109.16(13) . . ? 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' C1 N2 C2' -78.22(17) . . . . ? C9 C1 N2 C2' 154.44(12) . . . . ? C1' C1 N2 C3 163.21(13) . . . . ? C9 C1 N2 C3 35.87(14) . . . . ? C1' C1 N2 B 45.45(18) . . . . ? C9 C1 N2 B -81.88(15) . . . . ? C2' N2 C3 C4 -153.75(13) . . . . ? C1 N2 C3 C4 -35.12(14) . . . . ? B N2 C3 C4 85.69(14) . . . . ? N2 C3 C4 C5 -158.33(15) . . . . ? N2 C3 C4 C9 21.28(16) . . . . ? C9 C4 C5 C6 -0.5(2) . . . . ? C3 C4 C5 C6 179.10(15) . . . . ? C4 C5 C6 C7 -0.4(2) . . . . ? C5 C6 C7 C8 0.8(2) . . . . ? C6 C7 C8 C9 -0.3(2) . . . . ? C7 C8 C9 C4 -0.6(2) . . . . ? C7 C8 C9 C1 178.88(15) . . . . ? C5 C4 C9 C8 1.0(2) . . . . ? C3 C4 C9 C8 -178.63(14) . . . . ? C5 C4 C9 C1 -178.59(14) . . . . ? C3 C4 C9 C1 1.77(17) . . . . ? C1' C1 C9 C8 30.9(2) . . . . ? N2 C1 C9 C8 156.74(15) . . . . ? C1' C1 C9 C4 -149.56(14) . . . . ? N2 C1 C9 C4 -23.71(15) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.19 _refine_diff_density_min -0.16 _refine_diff_density_rms 0.03 #===end data_Compound_4b # BHNSIM _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H22 B N Si' _chemical_formula_sum 'C12 H22 B N Si' _chemical_formula_weight 219.21 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' 'B' 'B' 0.0013 0.0007 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 8.201(2) _cell_length_b 9.792(3) _cell_length_c 16.905(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1357.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 16.0 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.073 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997a)' _exptl_special_details ; Absolute configuration determined: Flack parameter = 0.00(14). ; _diffrn_ambient_temperature 150(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-3' _diffrn_reflns_number 5373 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.031 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2630 _reflns_number_gt 2464 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement STADI4 _computing_data_reduction 'X-RED (Stoe & Cie, 1997a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material SHELXL-97 _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^)+(0.036P)^2^+0.400P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'located from delta-F' _refine_ls_hydrogen_treatment 'idealised, then riding model - except BH3 (rigid group)' _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 0.00(14) _refine_ls_number_reflns 2630 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.13 _refine_ls_restrained_S_all 1.13 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3633(2) 0.43351(18) 0.82689(10) 0.0182(4) Uani 1 1 d . . . H1 H 0.4606 0.4343 0.7912 0.022 Uiso 1 1 calc R . . N2 N 0.40809(19) 0.35748(17) 0.90301(9) 0.0196(3) Uani 1 1 d . . . C3 C 0.3071(3) 0.4273(2) 0.96559(11) 0.0267(4) Uani 1 1 d . . . H3A H 0.1970 0.3863 0.9691 0.032 Uiso 1 1 calc R . . H3C H 0.3605 0.4213 1.0180 0.032 Uiso 1 1 calc R . . C3' C 0.2983(3) 0.5730(2) 0.93754(11) 0.0265(4) Uani 1 1 d . . . C4 C 0.2645(3) 0.6910(2) 0.97906(13) 0.0423(6) Uani 1 1 d . . . H4 H 0.2376 0.6875 1.0337 0.051 Uiso 1 1 calc R . . C5 C 0.2706(4) 0.8152(2) 0.93918(14) 0.0443(7) Uani 1 1 d . . . H5 H 0.2477 0.8974 0.9669 0.053 Uiso 1 1 calc R . . C6 C 0.3097(3) 0.8204(2) 0.85940(13) 0.0347(5) Uani 1 1 d . . . H6 H 0.3146 0.9060 0.8331 0.042 Uiso 1 1 calc R . . C7 C 0.3418(3) 0.70120(18) 0.81785(12) 0.0248(4) Uani 1 1 d . . . H7 H 0.3682 0.7047 0.7632 0.030 Uiso 1 1 calc R . . C7' C 0.3350(2) 0.57674(18) 0.85714(10) 0.0198(4) Uani 1 1 d . . . C2' C 0.5846(2) 0.3834(2) 0.91962(12) 0.0304(5) Uani 1 1 d . . . H2'A H 0.6050 0.4820 0.9198 0.046 Uiso 1 1 calc R . . H2'B H 0.6512 0.3401 0.8786 0.046 Uiso 1 1 calc R . . H2'C H 0.6131 0.3451 0.9714 0.046 Uiso 1 1 calc R . . B B 0.3791(3) 0.1936(2) 0.90315(13) 0.0239(5) Uani 1 1 d . . . H1B H 0.4492 0.1462 0.8534 0.036 Uiso 1 1 calc R . . H2B H 0.2460 0.1715 0.8955 0.036 Uiso 1 1 calc R . . H3B H 0.4220 0.1499 0.9607 0.036 Uiso 1 1 calc R . . Si Si 0.17790(6) 0.37079(5) 0.76746(3) 0.01893(13) Uani 1 1 d . . . C8 C -0.0097(2) 0.3721(2) 0.82979(12) 0.0271(4) Uani 1 1 d . . . H8A H -0.1025 0.3398 0.7984 0.041 Uiso 1 1 calc R . . H8B H -0.0310 0.4652 0.8482 0.041 Uiso 1 1 calc R . . H8C H 0.0059 0.3118 0.8754 0.041 Uiso 1 1 calc R . . C9 C 0.2106(3) 0.2040(2) 0.71648(12) 0.0294(5) Uani 1 1 d . . . H9A H 0.1116 0.1786 0.6875 0.044 Uiso 1 1 calc R . . H9B H 0.2356 0.1335 0.7558 0.044 Uiso 1 1 calc R . . H9C H 0.3018 0.2123 0.6793 0.044 Uiso 1 1 calc R . . C10 C 0.1540(3) 0.5000(2) 0.68686(12) 0.0282(5) Uani 1 1 d . . . H10A H 0.0609 0.4752 0.6535 0.042 Uiso 1 1 calc R . . H10B H 0.2533 0.5023 0.6546 0.042 Uiso 1 1 calc R . . H10C H 0.1352 0.5903 0.7102 0.042 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 C1 0.0197(9) 0.0185(8) 0.0164(8) 0.0031(7) 0.0007(7) -0.0007(7) N2 0.0222(8) 0.0205(8) 0.0162(7) 0.0022(6) -0.0004(6) 0.0005(7) C3 0.0397(12) 0.0245(9) 0.0158(8) 0.0006(7) 0.0034(9) 0.0025(10) C3' 0.0352(12) 0.0236(9) 0.0207(9) -0.0015(8) 0.0021(9) -0.0005(9) C4 0.0693(18) 0.0324(12) 0.0251(11) -0.0070(10) 0.0056(11) 0.0068(12) C5 0.0711(19) 0.0237(11) 0.0382(13) -0.0116(10) 0.0031(12) 0.0076(12) C6 0.0461(13) 0.0189(9) 0.0391(12) -0.0007(8) -0.0011(11) 0.0014(10) C7 0.0289(11) 0.0205(9) 0.0249(9) 0.0020(8) 0.0015(9) -0.0023(9) C7' 0.0197(9) 0.0211(8) 0.0185(8) -0.0021(7) -0.0014(8) -0.0001(8) C2' 0.0247(11) 0.0318(11) 0.0346(11) 0.0038(10) -0.0110(8) -0.0030(10) B 0.0280(12) 0.0184(10) 0.0253(10) 0.0039(9) -0.0009(9) 0.0032(9) Si 0.0200(2) 0.0189(2) 0.0178(2) -0.0001(2) -0.0010(2) -0.0017(2) C8 0.0207(9) 0.0274(10) 0.0333(10) 0.0025(10) -0.0011(8) 0.0009(9) C9 0.0344(12) 0.0248(10) 0.0289(11) -0.0076(8) -0.0043(9) -0.0025(9) C10 0.0325(12) 0.0291(10) 0.0229(9) 0.0052(8) -0.0054(9) -0.0013(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C7' 1.511(3) . ? C1 N2 1.531(2) . ? C1 Si 1.9231(19) . ? N2 C2' 1.496(2) . ? N2 C3 1.507(2) . ? N2 B 1.622(3) . ? C3 C3' 1.505(3) . ? C3' C4 1.380(3) . ? C3' C7' 1.393(3) . ? C4 C5 1.392(3) . ? C5 C6 1.387(3) . ? C6 C7 1.387(3) . ? C7 C7' 1.389(3) . ? Si C8 1.864(2) . ? Si C9 1.866(2) . ? Si C10 1.870(2) . ? 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 C7' C1 N2 101.75(14) . . ? C7' C1 Si 110.59(13) . . ? N2 C1 Si 118.25(12) . . ? C2' N2 C3 108.83(16) . . ? C2' N2 C1 107.90(15) . . ? C3 N2 C1 103.76(14) . . ? C2' N2 B 108.02(16) . . ? C3 N2 B 111.52(15) . . ? C1 N2 B 116.55(14) . . ? C3' C3 N2 103.59(15) . . ? C4 C3' C7' 121.16(19) . . ? C4 C3' C3 130.03(18) . . ? C7' C3' C3 108.80(16) . . ? C3' C4 C5 118.6(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C7 120.4(2) . . ? C6 C7 C7' 119.23(18) . . ? C7 C7' C3' 119.92(17) . . ? C7 C7' C1 130.27(16) . . ? C3' C7' C1 109.81(16) . . ? C8 Si C9 112.68(10) . . ? C8 Si C10 108.71(10) . . ? C9 Si C10 105.71(10) . . ? C8 Si C1 110.79(9) . . ? C9 Si C1 114.02(9) . . ? C10 Si C1 104.33(9) . . ? 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 C7' C1 N2 C2' -81.67(17) . . . . ? Si C1 N2 C2' 157.02(14) . . . . ? C7' C1 N2 C3 33.68(18) . . . . ? Si C1 N2 C3 -87.63(16) . . . . ? C7' C1 N2 B 156.67(15) . . . . ? Si C1 N2 B 35.4(2) . . . . ? C2' N2 C3 C3' 81.82(19) . . . . ? C1 N2 C3 C3' -32.9(2) . . . . ? B N2 C3 C3' -159.12(16) . . . . ? N2 C3 C3' C4 -159.2(2) . . . . ? N2 C3 C3' C7' 19.5(2) . . . . ? C7' C3' C4 C5 -1.1(4) . . . . ? C3 C3' C4 C5 177.4(2) . . . . ? C3' C4 C5 C6 0.0(4) . . . . ? C4 C5 C6 C7 0.7(4) . . . . ? C5 C6 C7 C7' -0.3(4) . . . . ? C6 C7 C7' C3' -0.8(3) . . . . ? C6 C7 C7' C1 179.7(2) . . . . ? C4 C3' C7' C7 1.6(3) . . . . ? C3 C3' C7' C7 -177.25(19) . . . . ? C4 C3' C7' C1 -178.9(2) . . . . ? C3 C3' C7' C1 2.3(2) . . . . ? N2 C1 C7' C7 156.9(2) . . . . ? Si C1 C7' C7 -76.6(2) . . . . ? N2 C1 C7' C3' -22.6(2) . . . . ? Si C1 C7' C3' 103.88(17) . . . . ? C7' C1 Si C8 -59.12(15) . . . . ? N2 C1 Si C8 57.55(16) . . . . ? C7' C1 Si C9 172.51(12) . . . . ? N2 C1 Si C9 -70.81(16) . . . . ? C7' C1 Si C10 57.69(14) . . . . ? N2 C1 Si C10 174.37(14) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.28 _refine_diff_density_min -0.15 _refine_diff_density_rms 0.04 #===end data_Compound_5b # SIMBHN _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H22 B N Si' _chemical_formula_sum 'C12 H22 B N Si' _chemical_formula_weight 219.21 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' 'B' 'B' 0.0013 0.0007 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 9.877(4) _cell_length_b 10.076(5) _cell_length_c 13.669(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1360.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16 _cell_measurement_theta_min 13 _cell_measurement_theta_max 14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'X-RED (Stoe & Cie, 1997b)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-3.1' _diffrn_reflns_number 3108 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_sigmaI/netI 0.034 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2647 _reflns_number_gt 2362 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement STADI4 _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _computing_publication_material SHELXL-97 _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^)+(0.066P)^2^+1.441P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'BH3 from delta-F, others placed geometrically' _refine_ls_hydrogen_treatment 'BH3 as rigid rotating group, others with riding model' _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 0.0(2) _refine_ls_number_reflns 2647 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.143 _refine_ls_wR_factor_gt 0.134 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1374(3) -0.0466(3) 0.1278(2) 0.0249(6) Uani 1 1 d . . . H1A H 0.1124 0.0223 0.1773 0.030 Uiso 1 1 calc R . . N2 N 0.0715(3) -0.1760(2) 0.16240(18) 0.0280(6) Uani 1 1 d . . . B B -0.0750(4) -0.1527(4) 0.2120(3) 0.0391(9) Uani 1 1 d . . . H1A H -0.1382 -0.1185 0.1628 0.059 Uiso 1 1 calc R . . H1B H -0.0666 -0.0883 0.2654 0.059 Uiso 1 1 calc R . . H1C H -0.1091 -0.2370 0.2379 0.059 Uiso 1 1 calc R . . C2' C 0.0610(4) -0.2728(3) 0.0799(2) 0.0345(7) Uani 1 1 d . . . H2'A H 0.1505 -0.2856 0.0505 0.052 Uiso 1 1 calc R . . H2'B H -0.0017 -0.2383 0.0305 0.052 Uiso 1 1 calc R . . H2'C H 0.0272 -0.3578 0.1047 0.052 Uiso 1 1 calc R . . C3 C 0.1690(3) -0.2337(3) 0.2357(2) 0.0315(7) Uani 1 1 d . . . H3A H 0.1480 -0.2024 0.3026 0.038 Uiso 1 1 calc R . . H3B H 0.1661 -0.3319 0.2347 0.038 Uiso 1 1 calc R . . C3' C 0.3046(3) -0.1837(3) 0.2027(2) 0.0281(7) Uani 1 1 d . . . C4 C 0.4319(3) -0.2273(3) 0.2295(2) 0.0338(7) Uani 1 1 d . . . H4A H 0.4424 -0.3035 0.2697 0.041 Uiso 1 1 calc R . . C5 C 0.5444(3) -0.1576(4) 0.1964(3) 0.0369(8) Uani 1 1 d . . . H5A H 0.6325 -0.1850 0.2157 0.044 Uiso 1 1 calc R . . C6 C 0.5294(3) -0.0494(3) 0.1360(2) 0.0350(8) Uani 1 1 d . . . H6A H 0.6073 -0.0040 0.1129 0.042 Uiso 1 1 calc R . . C7 C 0.4003(3) -0.0054(3) 0.1084(2) 0.0307(7) Uani 1 1 d . . . H7A H 0.3901 0.0698 0.0672 0.037 Uiso 1 1 calc R . . C7' C 0.2873(3) -0.0740(3) 0.1424(2) 0.0256(6) Uani 1 1 d . . . Si Si 0.09148(8) 0.02715(7) 0.00204(6) 0.0285(2) Uani 1 1 d . . . C11 C 0.1312(4) 0.2077(3) 0.0139(3) 0.0439(9) Uani 1 1 d . . . H11A H 0.1107 0.2528 -0.0479 0.066 Uiso 1 1 calc R . . H11B H 0.2274 0.2188 0.0293 0.066 Uiso 1 1 calc R . . H11C H 0.0763 0.2462 0.0664 0.066 Uiso 1 1 calc R . . C12 C 0.1985(4) -0.0481(3) -0.0954(2) 0.0348(7) Uani 1 1 d . . . H12A H 0.1740 -0.0099 -0.1589 0.052 Uiso 1 1 calc R . . H12B H 0.1836 -0.1443 -0.0970 0.052 Uiso 1 1 calc R . . H12C H 0.2940 -0.0299 -0.0817 0.052 Uiso 1 1 calc R . . C13 C -0.0911(4) 0.0127(4) -0.0321(3) 0.0449(8) Uani 1 1 d . . . H13A H -0.1054 0.0520 -0.0968 0.067 Uiso 1 1 calc R . . H13B H -0.1466 0.0595 0.0163 0.067 Uiso 1 1 calc R . . H13C H -0.1171 -0.0812 -0.0336 0.067 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 C1 0.0270(14) 0.0204(14) 0.0273(14) -0.0017(12) 0.0020(11) -0.0006(11) N2 0.0268(13) 0.0261(12) 0.0311(13) 0.0003(10) 0.0000(11) -0.0031(11) B 0.034(2) 0.042(2) 0.041(2) 0.0034(17) 0.0098(17) -0.0005(18) C2' 0.0399(19) 0.0290(15) 0.0347(16) -0.0032(13) -0.0026(14) -0.0064(14) C3 0.0341(18) 0.0294(15) 0.0311(16) 0.0034(13) 0.0005(13) -0.0002(14) C3' 0.0332(16) 0.0272(15) 0.0237(14) -0.0043(12) 0.0015(13) -0.0021(12) C4 0.0360(18) 0.0316(16) 0.0337(16) -0.0013(13) -0.0030(14) 0.0054(14) C5 0.0301(16) 0.0416(18) 0.0390(18) -0.0138(16) -0.0038(14) 0.0040(14) C6 0.0268(16) 0.0387(19) 0.0396(18) -0.0117(16) 0.0019(13) -0.0070(14) C7 0.0314(16) 0.0306(16) 0.0302(14) -0.0030(12) 0.0023(13) -0.0052(13) C7' 0.0278(15) 0.0249(15) 0.0243(14) -0.0051(11) -0.0019(11) -0.0009(12) Si 0.0313(4) 0.0262(4) 0.0281(4) 0.0018(4) 0.0002(4) 0.0030(3) C11 0.065(2) 0.0264(15) 0.0399(19) 0.0047(15) -0.0001(18) 0.0019(15) C12 0.0404(18) 0.0323(17) 0.0317(15) 0.0003(14) 0.0026(14) 0.0005(15) C13 0.0350(17) 0.054(2) 0.0454(18) 0.0123(16) -0.0024(15) 0.0053(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 C1 N2 1.532(4) . ? N2 C3 1.506(4) . ? C3 C3' 1.500(4) . ? C3' C4 1.381(5) . ? C4 C5 1.390(5) . ? C5 C6 1.375(5) . ? C6 C7 1.402(5) . ? C7 C7' 1.393(4) . ? C7' C1 1.520(4) . ? C7' C3' 1.390(4) . ? C1 Si 1.927(3) . ? Si C11 1.868(3) . ? Si C12 1.862(3) . ? Si C13 1.868(4) . ? N2 C2' 1.494(4) . ? N2 B 1.615(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 C7' C1 N2 102.6(2) . . ? C7' C1 Si 114.6(2) . . ? N2 C1 Si 120.2(2) . . ? C2' N2 C3 107.1(2) . . ? C2' N2 C1 110.6(2) . . ? C3 N2 C1 105.2(2) . . ? C2' N2 B 110.5(3) . . ? C3 N2 B 110.5(2) . . ? C1 N2 B 112.7(2) . . ? C3' C3 N2 104.0(2) . . ? C4 C3' C7' 121.5(3) . . ? C4 C3' C3 128.8(3) . . ? C7' C3' C3 109.6(3) . . ? C3' C4 C5 118.8(3) . . ? C6 C5 C4 120.6(3) . . ? C5 C6 C7 120.7(3) . . ? C7' C7 C6 118.8(3) . . ? C3' C7' C7 119.6(3) . . ? C3' C7' C1 110.0(3) . . ? C7 C7' C1 130.3(3) . . ? C12 Si C11 109.86(17) . . ? C12 Si C13 109.70(17) . . ? C11 Si C13 107.48(17) . . ? C12 Si C1 110.36(15) . . ? C11 Si C1 104.41(15) . . ? C13 Si C1 114.81(14) . . ? 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 C7' C1 N2 C2' -88.2(3) . . . . ? Si C1 N2 C2' 40.4(3) . . . . ? C7' C1 N2 C3 27.2(3) . . . . ? Si C1 N2 C3 155.8(2) . . . . ? C7' C1 N2 B 147.6(3) . . . . ? Si C1 N2 B -83.8(3) . . . . ? C2' N2 C3 C3' 89.0(3) . . . . ? C1 N2 C3 C3' -28.8(3) . . . . ? B N2 C3 C3' -150.6(3) . . . . ? N2 C3 C3' C4 -164.7(3) . . . . ? N2 C3 C3' C7' 19.6(3) . . . . ? C7' C3' C4 C5 1.3(4) . . . . ? C3 C3' C4 C5 -174.1(3) . . . . ? C3' C4 C5 C6 -1.7(5) . . . . ? C4 C5 C6 C7 1.4(5) . . . . ? C5 C6 C7 C7' -0.6(4) . . . . ? C4 C3' C7' C7 -0.5(4) . . . . ? C3 C3' C7' C7 175.7(3) . . . . ? C4 C3' C7' C1 -178.3(3) . . . . ? C3 C3' C7' C1 -2.2(3) . . . . ? C6 C7 C7' C3' 0.1(4) . . . . ? C6 C7 C7' C1 177.4(3) . . . . ? N2 C1 C7' C3' -15.7(3) . . . . ? Si C1 C7' C3' -147.8(2) . . . . ? N2 C1 C7' C7 166.8(3) . . . . ? Si C1 C7' C7 34.7(4) . . . . ? C7' C1 Si C12 37.3(2) . . . . ? N2 C1 Si C12 -85.7(3) . . . . ? C7' C1 Si C11 -80.7(2) . . . . ? N2 C1 Si C11 156.3(2) . . . . ? C7' C1 Si C13 161.9(2) . . . . ? N2 C1 Si C13 38.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.26 _refine_diff_density_min -0.21 _refine_diff_density_rms 0.05 #===end data_Compound_7 # BZNMBI _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 I N' _chemical_formula_weight 303.17 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' 'I' 'I' -0.4742 1.8119 '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 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.639(3) _cell_length_b 7.619(4) _cell_length_c 9.731(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.22(3) _cell_angle_gamma 90.00 _cell_volume 635.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 13.2 _cell_measurement_theta_max 16.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 2.486 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.334 _exptl_absorpt_correction_T_max 0.782 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3.0 _diffrn_reflns_number 3969 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2227 _reflns_number_gt 2207 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement 'STADI4 (Stoe & Cie, 1997a)' _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _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 w=1/[\s^2^(Fo^2^)+(0.017P)^2^+0.27P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(3) _refine_ls_number_reflns 2227 _refine_ls_number_parameters 129 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0127 _refine_ls_R_factor_gt 0.0125 _refine_ls_wR_factor_ref 0.0318 _refine_ls_wR_factor_gt 0.0317 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.086 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2883(6) 0.6575(6) 0.7263(5) 0.0194(8) Uani 1 d U . . H1 H 0.2559 0.5614 0.7865 0.023 Uiso 1 calc R . . C1' C 0.2859(3) 0.5884(4) 0.5778(2) 0.0267(5) Uani 1 d U . . H1'A H 0.1781 0.5537 0.5412 0.032 Uiso 1 calc R . . H1'B H 0.3187 0.6831 0.5181 0.032 Uiso 1 calc R . . C1" C 0.3941(3) 0.4312(4) 0.5726(3) 0.0380(6) Uani 1 d U . . H1"A H 0.3921 0.3922 0.4764 0.057 Uiso 1 calc R . . H1"B H 0.3590 0.3353 0.6283 0.057 Uiso 1 calc R . . H1"C H 0.5007 0.4649 0.6096 0.057 Uiso 1 calc R . . N2 N 0.17917(17) 0.8158(7) 0.73364(16) 0.0177(4) Uani 1 d U . . C2' C 0.1355(2) 0.8240(9) 0.87841(17) 0.0220(3) Uani 1 d U . . H2'A H 0.0694 0.7232 0.8942 0.033 Uiso 1 calc R . . H2'B H 0.0782 0.9330 0.8901 0.033 Uiso 1 calc R . . H2'C H 0.2303 0.8212 0.9452 0.033 Uiso 1 calc R . . C2" C 0.0303(2) 0.8155(9) 0.6362(2) 0.0257(6) Uani 1 d U . . H2"A H -0.0309 0.7111 0.6531 0.039 Uiso 1 calc R . . H2"B H 0.0545 0.8139 0.5404 0.039 Uiso 1 calc R . . H2"C H -0.0300 0.9211 0.6513 0.039 Uiso 1 calc R . . C3 C 0.2770(6) 0.9748(6) 0.7080(5) 0.0237(9) Uani 1 d U . . H3A H 0.2433 1.0807 0.7552 0.028 Uiso 1 calc R . . H3B H 0.2753 0.9992 0.6079 0.028 Uiso 1 calc R . . C4 C 0.4394(5) 0.9093(9) 0.7745(5) 0.0202(11) Uani 1 d U . . C5 C 0.5688(6) 1.0130(7) 0.8260(6) 0.0298(11) Uani 1 d U . . H5 H 0.5656 1.1374 0.8201 0.036 Uiso 1 calc R . . C6 C 0.7020(6) 0.9248(6) 0.8862(6) 0.0338(11) Uani 1 d U . . H6 H 0.7939 0.9887 0.9182 0.041 Uiso 1 calc R . . C7 C 0.6994(6) 0.7442(7) 0.8990(6) 0.0327(10) Uani 1 d U . . H7 H 0.7890 0.6860 0.9442 0.039 Uiso 1 calc R . . C8 C 0.5704(7) 0.6455(7) 0.8480(7) 0.0311(11) Uani 1 d U . . H8 H 0.5733 0.5211 0.8549 0.037 Uiso 1 calc R . . C9 C 0.4394(5) 0.7279(8) 0.7880(6) 0.0190(9) Uani 1 d U . . I I 0.946869(12) 1.32676(18) 0.767881(10) 0.02337(6) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0194(16) 0.0203(14) 0.0184(16) 0.0007(12) 0.0019(12) 0.0076(11) C1' 0.0276(12) 0.0303(12) 0.0223(12) -0.0039(10) 0.0031(10) -0.0001(10) C1" 0.0469(16) 0.0309(15) 0.0387(15) -0.0101(12) 0.0148(12) 0.0052(12) N2 0.0161(6) 0.0204(11) 0.0163(7) 0.0028(14) 0.0015(5) -0.0038(14) C2' 0.0191(8) 0.0292(9) 0.0184(8) -0.004(3) 0.0049(6) 0.001(3) C2" 0.0192(8) 0.0349(16) 0.0212(8) 0.0004(19) -0.0044(7) 0.0047(19) C3 0.0186(17) 0.0225(17) 0.031(2) 0.0043(14) 0.0047(14) 0.0042(13) C4 0.0157(17) 0.024(2) 0.021(2) -0.0045(11) 0.0049(14) -0.0021(12) C5 0.0213(18) 0.0232(19) 0.047(3) -0.0090(16) 0.0133(16) -0.0061(14) C6 0.022(2) 0.0376(19) 0.043(3) -0.0151(18) 0.0073(17) -0.0131(17) C7 0.0140(17) 0.0475(19) 0.036(2) 0.0015(17) 0.0012(16) -0.0015(16) C8 0.025(2) 0.025(2) 0.042(2) 0.0021(16) 0.0028(17) 0.0030(15) C9 0.0235(18) 0.0131(16) 0.0219(17) -0.0001(15) 0.0092(13) -0.0035(11) I 0.02708(8) 0.02406(8) 0.01971(8) -0.00115(12) 0.00580(4) -0.00243(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C9 1.468(7) . ? C1 C1' 1.535(5) . ? C1 N2 1.539(6) . ? C1' C1" 1.524(3) . ? N2 C2" 1.499(2) . ? N2 C2' 1.505(2) . ? N2 C3 1.516(6) . ? C3 C4 1.551(6) . ? C4 C9 1.388(4) . ? C4 C5 1.409(8) . ? C5 C6 1.396(8) . ? C6 C7 1.382(4) . ? C7 C8 1.384(8) . ? C8 C9 1.360(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 C1 C1' 114.6(4) . . ? C9 C1 N2 102.3(4) . . ? C1' C1 N2 112.2(3) . . ? C1" C1' C1 111.4(2) . . ? C2" N2 C2' 107.23(14) . . ? C2" N2 C3 110.5(4) . . ? C2' N2 C3 109.4(4) . . ? C2" N2 C1 116.8(4) . . ? C2' N2 C1 107.7(4) . . ? C3 N2 C1 105.14(15) . . ? N2 C3 C4 99.7(4) . . ? C9 C4 C5 122.3(6) . . ? C9 C4 C3 110.4(5) . . ? C5 C4 C3 127.1(6) . . ? C6 C5 C4 117.1(6) . . ? C7 C6 C5 119.7(6) . . ? C6 C7 C8 122.0(6) . . ? C9 C8 C7 119.5(6) . . ? C8 C9 C4 119.4(6) . . ? C8 C9 C1 131.0(6) . . ? C4 C9 C1 109.6(5) . . ? 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 C9 C1 C1' C1" 64.2(5) . . . . ? N2 C1 C1' C1" -179.8(3) . . . . ? C9 C1 N2 C2" 158.5(4) . . . . ? C1' C1 N2 C2" 35.2(5) . . . . ? C9 C1 N2 C2' -80.8(5) . . . . ? C1' C1 N2 C2' 155.8(3) . . . . ? C9 C1 N2 C3 35.7(4) . . . . ? C1' C1 N2 C3 -87.6(4) . . . . ? C2" N2 C3 C4 -159.2(3) . . . . ? C2' N2 C3 C4 83.0(4) . . . . ? C1 N2 C3 C4 -32.3(3) . . . . ? N2 C3 C4 C9 18.4(6) . . . . ? N2 C3 C4 C5 -156.8(5) . . . . ? C9 C4 C5 C6 3.1(9) . . . . ? C3 C4 C5 C6 177.8(5) . . . . ? C4 C5 C6 C7 -3.2(10) . . . . ? C5 C6 C7 C8 3.1(13) . . . . ? C6 C7 C8 C9 -2.6(11) . . . . ? C7 C8 C9 C4 2.3(10) . . . . ? C7 C8 C9 C1 180.0(6) . . . . ? C5 C4 C9 C8 -2.7(12) . . . . ? C3 C4 C9 C8 -178.1(5) . . . . ? C5 C4 C9 C1 179.2(4) . . . . ? C3 C4 C9 C1 3.7(8) . . . . ? C1' C1 C9 C8 -80.3(8) . . . . ? N2 C1 C9 C8 158.1(6) . . . . ? C1' C1 C9 C4 97.6(6) . . . . ? N2 C1 C9 C4 -24.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.29 _refine_diff_density_min -0.41 _refine_diff_density_rms 0.04 #===end