# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ; FIRST AUTHORS ADDRESS ; _publ_contact_author ; ENTER NAME ENTER ADDRESS ; _publ_contact_author_email E.J.THOMAS@MANCHESTER.AC.UK _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_section_title ; ENTER SECTION TITLE ; _publ_contact_author_name E.Thomas _publ_author_name E.Thomas data_S530 _database_code_depnum_ccdc_archive 'CCDC 122890' #TrackingRef '- OriginalPlus.cif' #------------------------------------------------------------------------------ _audit_creation_date 1997-06-19 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., Garcia-Granda, S., Gould, R.O., Smits, J.M.M. and Smykalla, C. (1992). The DIRDIF program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; 'DIRDIF92 PATTY (Beurskens, 1992) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 10.390(2) _cell_length_b 17.643(3) _cell_length_c 8.429(2) _cell_angle_alpha 92.81(2) _cell_angle_beta 113.88(1) _cell_angle_gamma 90.83(1) _cell_volume 1410.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.4 _cell_measurement_theta_max 14.3 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour clear _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.493 _chemical_formula_weight 634.18 _chemical_formula_analytical ? _chemical_formula_sum 'C31 H31 Br O2 Sn ' _chemical_formula_moiety 'C31 H31 Br O2 Sn ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 636.00 _exptl_absorpt_coefficient_mu 2.351 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.31+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -3.16 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 -4 1 0 1 -3 -4 -2 1 _diffrn_reflns_number 5290 _reflns_number_total 4987 _reflns_number_observed 3413 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.02427 _diffrn_reflns_av_sigmaI/netI 0.066 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.07279 _diffrn_orient_matrix_UB_12 0.03953 _diffrn_orient_matrix_UB_13 -0.03414 _diffrn_orient_matrix_UB_21 0.07606 _diffrn_orient_matrix_UB_22 0.04077 _diffrn_orient_matrix_UB_23 0.04549 _diffrn_orient_matrix_UB_31 0.00331 _diffrn_orient_matrix_UB_32 0.00053 _diffrn_orient_matrix_UB_33 -0.11686 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 62 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 62 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; Br 0 2 -0.290 2.459 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 4 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Sn 0 2 -0.654 1.425 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Sn1 0.21934(5) 0.20178(3) 0.45446(6) 0.0439(1) 1.000 . Uani d ? Br1 -0.69727(8) 0.58095(5) 0.2088(1) 0.0753(3) 1.000 . Uani d ? O1 -0.0422(5) 0.5695(3) 0.1875(7) 0.078(2) 1.000 . Uani d ? O2 -0.0696(5) 0.4557(3) 0.2773(6) 0.066(2) 1.000 . Uani d ? C1 0.0363(6) 0.1740(4) 0.4992(8) 0.046(2) 1.000 . Uani d ? C2 -0.0138(8) 0.2218(4) 0.5951(10) 0.074(3) 1.000 . Uani d ? C3 -0.1317(9) 0.2018(5) 0.618(1) 0.089(3) 1.000 . Uani d ? C4 -0.1985(8) 0.1333(6) 0.558(1) 0.091(4) 1.000 . Uani d ? C5 -0.1527(8) 0.0840(5) 0.464(1) 0.082(3) 1.000 . Uani d ? C6 -0.0352(7) 0.1046(4) 0.4348(9) 0.061(2) 1.000 . Uani d ? C7 0.2304(6) 0.1174(4) 0.2717(8) 0.050(2) 1.000 . Uani d ? C8 0.1323(7) 0.1108(4) 0.0987(9) 0.066(3) 1.000 . Uani d ? C9 0.1392(8) 0.0552(5) -0.0180(9) 0.075(3) 1.000 . Uani d ? C10 0.2466(10) 0.0057(4) 0.035(1) 0.080(3) 1.000 . Uani d ? C11 0.3441(9) 0.0101(4) 0.203(1) 0.081(3) 1.000 . Uani d ? C12 0.3362(8) 0.0653(4) 0.3194(9) 0.067(3) 1.000 . Uani d ? C13 0.3930(6) 0.1892(3) 0.6980(7) 0.042(2) 1.000 . Uani d ? C14 0.3685(7) 0.1683(4) 0.8365(9) 0.065(2) 1.000 . Uani d ? C15 0.4772(9) 0.1628(4) 0.9995(9) 0.076(3) 1.000 . Uani d ? C16 0.6118(8) 0.1784(4) 1.0216(9) 0.067(3) 1.000 . Uani d ? C17 0.6392(7) 0.1978(4) 0.8843(9) 0.061(2) 1.000 . Uani d ? C18 0.5299(7) 0.2035(4) 0.7242(8) 0.053(2) 1.000 . Uani d ? C19 0.2133(6) 0.3156(3) 0.3671(7) 0.046(2) 1.000 . Uani d ? C20 0.2800(7) 0.3218(4) 0.2371(8) 0.061(2) 1.000 . Uani d ? C21 0.4319(8) 0.3028(4) 0.3050(10) 0.078(3) 1.000 . Uani d ? C22 -0.0430(7) 0.3023(4) 0.1518(9) 0.076(3) 1.000 . Uani d ? C23 0.0665(6) 0.3470(4) 0.3099(8) 0.054(2) 1.000 . Uani d ? C24 0.0622(7) 0.4308(4) 0.2761(8) 0.060(2) 1.000 . Uani d ? C25 -0.1111(8) 0.5246(4) 0.2256(8) 0.056(2) 1.000 . Uani d ? C26 -0.2520(7) 0.5369(4) 0.2246(7) 0.048(2) 1.000 . Uani d ? C27 -0.3177(7) 0.4872(4) 0.2903(9) 0.060(2) 1.000 . Uani d ? C28 -0.4491(7) 0.5007(4) 0.2869(9) 0.064(2) 1.000 . Uani d ? C29 -0.5173(7) 0.5640(4) 0.2133(8) 0.055(2) 1.000 . Uani d ? C30 -0.4537(7) 0.6145(4) 0.1454(8) 0.055(2) 1.000 . Uani d ? C31 -0.3215(7) 0.6016(3) 0.1534(8) 0.056(2) 1.000 . Uani d ? H2 0.0345 0.2689 0.6449 0.089 1.000 . Uiso c ? H3 -0.1678 0.2366 0.6783 0.107 1.000 . Uiso c ? H4 -0.2776 0.1194 0.5815 0.109 1.000 . Uiso c ? H5 -0.2006 0.0364 0.4192 0.099 1.000 . Uiso c ? H6 -0.0029 0.0704 0.3694 0.073 1.000 . Uiso c ? H8 0.0586 0.1457 0.0604 0.079 1.000 . Uiso c ? H9 0.0701 0.0513 -0.1342 0.090 1.000 . Uiso c ? H10 0.2531 -0.0321 -0.0454 0.096 1.000 . Uiso c ? H11 0.4177 -0.0249 0.2390 0.097 1.000 . Uiso c ? H12 0.4050 0.0678 0.4357 0.081 1.000 . Uiso c ? H14 0.2744 0.1572 0.8216 0.078 1.000 . Uiso c ? H15 0.4573 0.1482 1.0945 0.091 1.000 . Uiso c ? H16 0.6867 0.1757 1.1329 0.081 1.000 . Uiso c ? H17 0.7336 0.2075 0.8986 0.074 1.000 . Uiso c ? H18 0.5503 0.2178 0.6294 0.063 1.000 . Uiso c ? H19 0.2715 0.3465 0.4668 0.055 1.000 . Uiso c ? H20a 0.2292 0.2880 0.1392 0.073 1.000 . Uiso c ? H20b 0.2719 0.3724 0.2019 0.073 1.000 . Uiso c ? H21a 0.4427 0.2530 0.3455 0.093 1.000 . Uiso c ? H21b 0.4854 0.3382 0.3980 0.093 1.000 . Uiso c ? H21c 0.4640 0.3052 0.2146 0.093 1.000 . Uiso c ? H22a -0.0184 0.3058 0.0553 0.091 1.000 . Uiso c ? H22b -0.1330 0.3227 0.1247 0.091 1.000 . Uiso c ? H22c -0.0456 0.2505 0.1771 0.091 1.000 . Uiso c ? H23 0.0386 0.3418 0.4032 0.065 1.000 . Uiso c ? H24a 0.0648 0.4379 0.1665 0.072 1.000 . Uiso c ? H24b 0.1395 0.4580 0.3648 0.072 1.000 . Uiso c ? H27 -0.2718 0.4425 0.3392 0.072 1.000 . Uiso c ? H28 -0.4921 0.4662 0.3355 0.077 1.000 . Uiso c ? H30 -0.5014 0.6583 0.0932 0.066 1.000 . Uiso c ? H31 -0.2769 0.6374 0.1096 0.067 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Sn1 0.0414(3) 0.0467(3) 0.0453(3) 0.0036(2) 0.0190(2) 0.0055(2) Br1 0.0598(5) 0.0771(6) 0.0845(6) 0.0097(4) 0.0240(4) 0.0082(5) O1 0.083(4) 0.056(3) 0.117(4) 0.014(3) 0.060(3) 0.023(3) O2 0.062(3) 0.055(3) 0.090(4) 0.017(2) 0.038(3) 0.018(3) C1 0.039(4) 0.050(4) 0.049(4) 0.006(3) 0.018(3) 0.009(3) C2 0.076(5) 0.075(6) 0.090(6) 0.001(4) 0.054(5) 0.008(4) C3 0.091(7) 0.081(7) 0.126(8) 0.016(5) 0.075(6) 0.012(6) C4 0.068(6) 0.105(8) 0.126(8) 0.012(5) 0.061(6) 0.038(6) C5 0.064(5) 0.087(7) 0.099(7) -0.007(5) 0.036(5) 0.018(5) C6 0.052(4) 0.067(5) 0.069(5) 0.002(4) 0.030(4) 0.010(4) C7 0.046(4) 0.057(5) 0.048(4) 0.003(3) 0.019(3) 0.008(3) C8 0.064(5) 0.064(5) 0.070(5) 0.007(4) 0.029(4) 0.002(4) C9 0.087(6) 0.074(6) 0.057(5) -0.006(5) 0.024(4) -0.013(4) C10 0.116(7) 0.056(5) 0.078(6) 0.005(5) 0.052(6) -0.014(5) C11 0.104(7) 0.062(6) 0.080(6) 0.026(5) 0.040(5) 0.008(5) C12 0.088(6) 0.055(5) 0.059(5) 0.010(4) 0.030(4) 0.001(4) C13 0.047(4) 0.039(4) 0.038(4) 0.007(3) 0.015(3) 0.004(3) C14 0.058(5) 0.082(6) 0.057(5) -0.005(4) 0.025(4) 0.011(4) C15 0.091(6) 0.093(6) 0.049(5) 0.008(5) 0.033(5) 0.020(4) C16 0.064(5) 0.072(5) 0.051(5) 0.011(4) 0.009(4) 0.002(4) C17 0.051(4) 0.067(5) 0.062(5) 0.006(4) 0.018(4) 0.005(4) C18 0.054(4) 0.061(5) 0.046(4) 0.007(4) 0.024(4) 0.008(3) C19 0.046(4) 0.046(4) 0.044(4) 0.001(3) 0.017(3) 0.004(3) C20 0.059(5) 0.064(5) 0.060(5) 0.004(4) 0.024(4) 0.014(4) C21 0.089(6) 0.068(5) 0.105(6) 0.016(4) 0.067(5) 0.024(5) C22 0.057(5) 0.056(5) 0.087(6) 0.007(4) -0.002(4) 0.007(4) C23 0.048(4) 0.050(4) 0.057(4) 0.005(3) 0.014(3) 0.006(3) C24 0.055(4) 0.057(5) 0.065(5) 0.010(4) 0.020(4) 0.006(4) C25 0.070(5) 0.046(5) 0.050(4) 0.008(4) 0.021(4) 0.006(3) C26 0.054(4) 0.047(4) 0.039(4) 0.002(3) 0.016(3) -0.002(3) C27 0.059(5) 0.047(4) 0.074(5) 0.011(4) 0.025(4) 0.010(4) C28 0.065(5) 0.050(5) 0.075(5) -0.001(4) 0.026(4) 0.005(4) C29 0.054(4) 0.054(5) 0.045(4) -0.001(4) 0.010(3) -0.004(3) C30 0.067(5) 0.044(4) 0.056(4) 0.017(4) 0.026(4) 0.010(3) C31 0.082(5) 0.038(4) 0.055(4) 0.008(4) 0.036(4) 0.006(3) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00005|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3634 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_obs 0.0403 _refine_ls_wR_factor_all 0.0473 _refine_ls_wR_factor_obs 0.0381 _refine_ls_goodness_of_fit_all 1.744 _refine_ls_goodness_of_fit_obs 1.724 _refine_ls_shift/esd_max 0.0010 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.38 _refine_diff_density_max 0.70 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag SN1 C1 2.138(6) . . yes SN1 C7 2.127(6) . . yes SN1 C13 2.139(6) . . yes SN1 C19 2.166(6) . . yes BR1 C29 1.883(6) . . yes O1 C25 1.199(7) . . yes O2 C24 1.449(7) . . yes O2 C25 1.330(7) . . yes C1 C2 1.386(8) . . yes C1 C6 1.390(8) . . yes C2 C3 1.361(9) . . yes C2 H2 0.95 . . no C3 C4 1.35(1) . . yes C3 H3 0.95 . . no C4 C5 1.36(1) . . yes C4 H4 0.95 . . no C5 C6 1.385(9) . . yes C5 H5 0.95 . . no C6 H6 0.95 . . no C7 C8 1.399(8) . . yes C7 C12 1.386(8) . . yes C8 C9 1.378(9) . . yes C8 H8 0.95 . . no C9 C10 1.368(10) . . yes C9 H9 0.95 . . no C10 C11 1.362(10) . . yes C10 H10 0.95 . . no C11 C12 1.378(9) . . yes C11 H11 0.95 . . no C12 H12 0.95 . . no C13 C14 1.358(8) . . yes C13 C18 1.365(8) . . yes C14 C15 1.391(9) . . yes C14 H14 0.95 . . no C15 C16 1.356(9) . . yes C15 H15 0.95 . . no C16 C17 1.357(9) . . yes C16 H16 0.95 . . no C17 C18 1.377(8) . . yes C17 H17 0.95 . . no C18 H18 0.95 . . no C19 C20 1.522(8) . . yes C19 C23 1.523(8) . . yes C19 H19 0.95 . . no C20 C21 1.494(9) . . yes C20 H20a 0.95 . . no C20 H20b 0.95 . . no C21 H21a 0.95 . . no C21 H21b 0.95 . . no C21 H21c 0.95 . . no C22 C23 1.529(8) . . yes C22 H22a 0.95 . . no C22 H22b 0.95 . . no C22 H22c 0.95 . . no C23 C24 1.516(8) . . yes C23 H23 0.95 . . no C24 H24a 0.95 . . no C24 H24b 0.95 . . no C25 C26 1.480(8) . . yes C26 C27 1.371(8) . . yes C26 C31 1.387(8) . . yes C27 C28 1.378(8) . . yes C27 H27 0.95 . . no C28 C29 1.367(8) . . yes C28 H28 0.95 . . no C29 C30 1.378(8) . . yes C30 C31 1.371(8) . . yes C30 H30 0.95 . . no C31 H31 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 SN1 C7 106.9(2) . . . yes C1 SN1 C13 105.0(2) . . . yes C1 SN1 C19 111.5(2) . . . yes C7 SN1 C13 108.2(2) . . . yes C7 SN1 C19 112.6(2) . . . yes C13 SN1 C19 112.1(2) . . . yes C24 O2 C25 118.4(5) . . . yes SN1 C1 C2 122.9(5) . . . yes SN1 C1 C6 119.8(5) . . . yes C2 C1 C6 117.3(6) . . . yes C1 C2 C3 120.6(7) . . . yes C1 C2 H2 119.7 . . . no C3 C2 H2 119.7 . . . no C2 C3 C4 121.3(8) . . . yes C2 C3 H3 119.3 . . . no C4 C3 H3 119.3 . . . no C3 C4 C5 120.2(8) . . . yes C3 C4 H4 119.9 . . . no C5 C4 H4 119.9 . . . no C4 C5 C6 119.1(8) . . . yes C4 C5 H5 120.5 . . . no C6 C5 H5 120.5 . . . no C1 C6 C5 121.4(7) . . . yes C1 C6 H6 119.3 . . . no C5 C6 H6 119.3 . . . no SN1 C7 C8 122.5(5) . . . yes SN1 C7 C12 121.2(5) . . . yes C8 C7 C12 116.3(6) . . . yes C7 C8 C9 122.0(7) . . . yes C7 C8 H8 119.0 . . . no C9 C8 H8 119.0 . . . no C8 C9 C10 119.4(7) . . . yes C8 C9 H9 120.3 . . . no C10 C9 H9 120.3 . . . no C9 C10 C11 120.4(7) . . . yes C9 C10 H10 119.8 . . . no C11 C10 H10 119.8 . . . no C10 C11 C12 120.1(7) . . . yes C10 C11 H11 120.0 . . . no C12 C11 H11 120.0 . . . no C7 C12 C11 121.8(7) . . . yes C7 C12 H12 119.1 . . . no C11 C12 H12 119.1 . . . no SN1 C13 C14 119.6(5) . . . yes SN1 C13 C18 123.1(4) . . . yes C14 C13 C18 117.2(6) . . . yes C13 C14 C15 121.9(6) . . . yes C13 C14 H14 119.1 . . . no C15 C14 H14 119.1 . . . no C14 C15 C16 119.4(6) . . . yes C14 C15 H15 120.3 . . . no C16 C15 H15 120.3 . . . no C15 C16 C17 119.8(6) . . . yes C15 C16 H16 120.1 . . . no C17 C16 H16 120.1 . . . no C16 C17 C18 119.8(6) . . . yes C16 C17 H17 120.1 . . . no C18 C17 H17 120.1 . . . no C13 C18 C17 121.9(6) . . . yes C13 C18 H18 119.1 . . . no C17 C18 H18 119.1 . . . no SN1 C19 C20 112.3(4) . . . yes SN1 C19 C23 111.5(4) . . . yes SN1 C19 H19 105.7 . . . no C20 C19 C23 115.0(5) . . . yes C20 C19 H19 105.7 . . . no C23 C19 H19 105.7 . . . no C19 C20 C21 114.7(5) . . . yes C19 C20 H20a 108.2 . . . no C19 C20 H20b 108.2 . . . no C21 C20 H20a 108.2 . . . no C21 C20 H20b 108.2 . . . no H20a C20 H20b 109.5 . . . no C20 C21 H21a 109.5 . . . no C20 C21 H21b 109.5 . . . no C20 C21 H21c 109.5 . . . no H21a C21 H21b 109.5 . . . no H21a C21 H21c 109.5 . . . no H21b C21 H21c 109.5 . . . no C23 C22 H22a 109.5 . . . no C23 C22 H22b 109.5 . . . no C23 C22 H22c 109.5 . . . no H22a C22 H22b 109.5 . . . no H22a C22 H22c 109.5 . . . no H22b C22 H22c 109.5 . . . no C19 C23 C22 112.9(5) . . . yes C19 C23 C24 113.4(5) . . . yes C19 C23 H23 106.8 . . . no C22 C23 C24 109.7(5) . . . yes C22 C23 H23 106.8 . . . no C24 C23 H23 106.8 . . . no O2 C24 C23 105.5(5) . . . yes O2 C24 H24a 110.5 . . . no O2 C24 H24b 110.5 . . . no C23 C24 H24a 110.5 . . . no C23 C24 H24b 110.5 . . . no H24a C24 H24b 109.5 . . . no O1 C25 O2 124.1(7) . . . yes O1 C25 C26 126.0(6) . . . yes O2 C25 C26 109.9(6) . . . yes C25 C26 C27 123.1(6) . . . yes C25 C26 C31 118.7(6) . . . yes C27 C26 C31 118.2(6) . . . yes C26 C27 C28 121.3(6) . . . yes C26 C27 H27 119.3 . . . no C28 C27 H27 119.3 . . . no C27 C28 C29 119.7(6) . . . yes C27 C28 H28 120.1 . . . no C29 C28 H28 120.1 . . . no BR1 C29 C28 119.0(5) . . . yes BR1 C29 C30 121.1(5) . . . yes C28 C29 C30 120.0(6) . . . yes C29 C30 C31 119.9(6) . . . yes C29 C30 H30 120.1 . . . no C31 C30 H30 120.1 . . . no C26 C31 C30 120.9(6) . . . yes C26 C31 H31 119.6 . . . no C30 C31 H31 119.6 . . . no #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ 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 SN1 C1 C2 C3 179.4(6) . . . . no SN1 C1 C6 C5 178.8(5) . . . . no SN1 C7 C8 C9 -179.0(6) . . . . no SN1 C7 C12 C11 179.6(6) . . . . no SN1 C13 C14 C15 -177.0(6) . . . . no SN1 C13 C18 C17 177.4(5) . . . . no SN1 C19 C20 C21 -60.6(7) . . . . no SN1 C19 C23 C22 -64.1(6) . . . . no SN1 C19 C23 C24 170.4(4) . . . . no BR1 C29 C28 C27 179.6(5) . . . . no BR1 C29 C30 C31 178.7(5) . . . . no O1 C25 O2 C24 -4.7(10) . . . . no O1 C25 C26 C27 -171.5(7) . . . . no O1 C25 C26 C31 8(1) . . . . no O2 C24 C23 C19 -162.7(5) . . . . no O2 C24 C23 C22 70.1(7) . . . . no O2 C25 C26 C27 7.9(9) . . . . no O2 C25 C26 C31 -171.9(5) . . . . no C1 SN1 C7 C8 68.0(6) . . . . no C1 SN1 C7 C12 -111.6(5) . . . . no C1 SN1 C13 C14 -0.7(6) . . . . no C1 SN1 C13 C18 -178.6(5) . . . . no C1 SN1 C19 C20 -145.2(4) . . . . no C1 SN1 C19 C23 -14.5(5) . . . . no C1 C2 C3 C4 3(1) . . . . no C1 C6 C5 C4 0(1) . . . . no C2 C1 SN1 C7 -171.9(5) . . . . no C2 C1 SN1 C13 73.3(6) . . . . no C2 C1 SN1 C19 -48.3(6) . . . . no C2 C1 C6 C5 0(1) . . . . no C2 C3 C4 C5 -3(1) . . . . no C3 C2 C1 C6 -2(1) . . . . no C3 C4 C5 C6 1(1) . . . . no C6 C1 SN1 C7 10.0(6) . . . . no C6 C1 SN1 C13 -104.8(5) . . . . no C6 C1 SN1 C19 133.5(5) . . . . no C7 SN1 C13 C14 -114.6(5) . . . . no C7 SN1 C13 C18 67.5(5) . . . . no C7 SN1 C19 C20 -25.0(5) . . . . no C7 SN1 C19 C23 105.8(4) . . . . no C7 C8 C9 C10 -1(1) . . . . no C7 C12 C11 C10 0(1) . . . . no C8 C7 SN1 C13 -179.3(5) . . . . no C8 C7 SN1 C19 -54.8(6) . . . . no C8 C7 C12 C11 0(1) . . . . no C8 C9 C10 C11 1(1) . . . . no C9 C8 C7 C12 0(1) . . . . no C9 C10 C11 C12 0(1) . . . . no C12 C7 SN1 C13 1.1(6) . . . . no C12 C7 SN1 C19 125.6(5) . . . . no C13 SN1 C19 C20 97.3(4) . . . . no C13 SN1 C19 C23 -131.9(4) . . . . no C13 C14 C15 C16 0(1) . . . . no C13 C18 C17 C16 0(1) . . . . no C14 C13 SN1 C19 120.6(5) . . . . no C14 C13 C18 C17 -0.5(10) . . . . no C14 C15 C16 C17 -1(1) . . . . no C15 C14 C13 C18 1(1) . . . . no C15 C16 C17 C18 1(1) . . . . no C18 C13 SN1 C19 -57.3(6) . . . . no C20 C19 C23 C22 65.3(7) . . . . no C20 C19 C23 C24 -60.2(7) . . . . no C21 C20 C19 C23 170.4(6) . . . . no C23 C24 O2 C25 -170.2(5) . . . . no C24 O2 C25 C26 176.0(5) . . . . no C25 C26 C27 C28 -180.0(6) . . . . no C25 C26 C31 C30 178.3(6) . . . . no C26 C27 C28 C29 1(1) . . . . no C26 C31 C30 C29 1.9(10) . . . . no C27 C26 C31 C30 -1.5(10) . . . . no C27 C28 C29 C30 -1(1) . . . . no C28 C27 C26 C31 0(1) . . . . no C28 C29 C30 C31 0(1) . . . . no #----------------------------------------------------------------------------- _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_theta_max 25.33 _diffrn_measured_fraction_theta_max 0.969 _chemical_name_common 'C31 H31 Br1 O2 Sn1'