# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Christoph Schneider' 'Harald Krautscheid' 'Mecheril Valsan Nandakumar' 'Andreas Tschop' _publ_contact_author_name 'Christoph Schneider' _publ_contact_author_address ; Chemistry University of Leipzig Johannisallee 29 Leipzig D-04103 GERMANY ; _publ_contact_author_email SCHNEIDER@CHEMIE.UNI-LEIPZIG.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Indium-Bipyridine-Catalyzed, Enantioselective Thiolysis of meso-Epoxides ; data_206y _database_code_depnum_ccdc_archive 'CCDC 640641' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '[InBr2(C20H28N2O2)(H2O)]Br*C4H8O*4H2O' _chemical_formula_sum 'C24 H46 Br3 In N2 O8' _chemical_formula_weight 845.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' In In -0.7276 1.3100 '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 P2(1)2(1)2(1) #(No. 19) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, -y, z+1/2' _cell_length_a 8.3069(3) _cell_length_b 17.0302(6) _cell_length_c 23.6466(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3345.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 36037 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 29.6 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 4.333 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1650 _exptl_absorpt_correction_T_max 0.6965 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 IPDS-2T' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26247 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.00 _reflns_number_total 7293 _reflns_number_gt 6771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-AREA, STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND2 (Brandenburg, 1999)' _computing_publication_material ? _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^)+(0.0406P)^2^+5.0827P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00047(13) _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 0.019(9) _refine_ls_number_reflns 7293 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.004 _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 In1 In 0.27087(4) 0.51447(2) 0.178844(15) 0.02739(9) Uani 1 1 d . . . Br1 Br 0.49087(7) 0.59818(4) 0.13072(2) 0.03747(14) Uani 1 1 d . . . Br2 Br 0.05432(7) 0.42397(3) 0.22168(3) 0.04062(14) Uani 1 1 d . . . O1 O 0.0841(5) 0.5487(2) 0.11031(15) 0.0327(8) Uani 1 1 d . . . HO1 H 0.043(13) 0.511(6) 0.072(4) 0.11(3) Uiso 1 1 d . . . O2 O 0.4755(5) 0.4367(2) 0.21274(17) 0.0358(9) Uani 1 1 d . . . HO2 H 0.528(9) 0.417(4) 0.183(3) 0.048(19) Uiso 1 1 d . . . O3 O 0.3132(5) 0.4262(2) 0.11027(18) 0.0373(9) Uani 1 1 d . . . HO3A H 0.368(8) 0.430(4) 0.081(3) 0.029(16) Uiso 1 1 d . . . HO3B H 0.354(9) 0.370(4) 0.110(3) 0.047(19) Uiso 1 1 d . . . N1 N 0.1164(5) 0.6205(2) 0.20623(17) 0.0274(9) Uani 1 1 d . . . N2 N 0.3701(5) 0.5610(2) 0.26351(17) 0.0286(9) Uani 1 1 d . . . C1 C -0.0196(6) 0.6377(3) 0.1793(2) 0.0263(9) Uani 1 1 d . . . C2 C -0.1389(7) 0.6814(3) 0.2061(2) 0.0336(11) Uani 1 1 d . . . H2 H -0.2395 0.6897 0.1880 0.040 Uiso 1 1 calc R . . C3 C -0.1109(8) 0.7128(3) 0.2594(2) 0.0374(13) Uani 1 1 d . . . H3 H -0.1903 0.7439 0.2778 0.045 Uiso 1 1 calc R . . C4 C 0.0371(7) 0.6976(3) 0.2855(2) 0.0338(12) Uani 1 1 d . . . H4 H 0.0619 0.7199 0.3213 0.041 Uiso 1 1 calc R . . C5 C 0.1458(7) 0.6499(3) 0.2586(2) 0.0318(11) Uani 1 1 d . . . C6 C 0.3023(7) 0.6272(3) 0.2839(2) 0.0298(11) Uani 1 1 d . . . C7 C 0.3801(8) 0.6716(3) 0.3248(3) 0.0392(12) Uani 1 1 d . . . H7 H 0.3305 0.7170 0.3403 0.047 Uiso 1 1 calc R . . C8 C 0.5304(9) 0.6483(4) 0.3423(3) 0.0461(15) Uani 1 1 d . . . H8 H 0.5875 0.6787 0.3694 0.055 Uiso 1 1 calc R . . C9 C 0.5989(8) 0.5804(3) 0.3204(3) 0.0427(13) Uani 1 1 d . . . H9 H 0.7045 0.5651 0.3311 0.051 Uiso 1 1 calc R . . C10 C 0.5108(7) 0.5353(3) 0.2827(2) 0.0342(12) Uani 1 1 d . . . C11 C -0.0387(7) 0.6062(3) 0.1196(2) 0.0297(10) Uani 1 1 d . . . H11 H -0.1459 0.5798 0.1166 0.036 Uiso 1 1 calc R . . C12 C -0.0284(7) 0.6704(3) 0.0730(2) 0.0345(12) Uani 1 1 d . . . C13 C 0.1334(9) 0.7112(4) 0.0749(3) 0.0531(17) Uani 1 1 d . . . H13A H 0.2194 0.6723 0.0706 0.080 Uiso 1 1 calc R . . H13B H 0.1455 0.7383 0.1112 0.080 Uiso 1 1 calc R . . H13C H 0.1401 0.7495 0.0441 0.080 Uiso 1 1 calc R . . C14 C -0.1620(9) 0.7320(4) 0.0792(3) 0.0471(15) Uani 1 1 d . . . H14A H -0.1681 0.7636 0.0446 0.071 Uiso 1 1 calc R . . H14B H -0.1380 0.7662 0.1114 0.071 Uiso 1 1 calc R . . H14C H -0.2652 0.7055 0.0854 0.071 Uiso 1 1 calc R . . C15 C -0.0528(11) 0.6289(5) 0.0156(3) 0.0576(18) Uani 1 1 d . . . H15A H -0.1652 0.6119 0.0122 0.086 Uiso 1 1 calc R . . H15B H 0.0181 0.5830 0.0134 0.086 Uiso 1 1 calc R . . H15C H -0.0270 0.6653 -0.0151 0.086 Uiso 1 1 calc R . . C16 C 0.5731(7) 0.4577(3) 0.2607(2) 0.0371(12) Uani 1 1 d . . . H16 H 0.6867 0.4649 0.2477 0.045 Uiso 1 1 calc R . . C17 C 0.5685(8) 0.3902(3) 0.3058(3) 0.0423(14) Uani 1 1 d . . . C18 C 0.3986(9) 0.3818(4) 0.3306(3) 0.0587(19) Uani 1 1 d . . . H18A H 0.3983 0.3401 0.3592 0.088 Uiso 1 1 calc R . . H18B H 0.3230 0.3683 0.3003 0.088 Uiso 1 1 calc R . . H18C H 0.3660 0.4315 0.3480 0.088 Uiso 1 1 calc R . . C19 C 0.6871(10) 0.4068(5) 0.3531(3) 0.061(2) Uani 1 1 d . . . H19A H 0.7016 0.3593 0.3760 0.091 Uiso 1 1 calc R . . H19B H 0.6455 0.4492 0.3770 0.091 Uiso 1 1 calc R . . H19C H 0.7907 0.4225 0.3368 0.091 Uiso 1 1 calc R . . C20 C 0.6161(13) 0.3139(4) 0.2770(3) 0.068(2) Uani 1 1 d . . . H20A H 0.7231 0.3196 0.2600 0.103 Uiso 1 1 calc R . . H20B H 0.5376 0.3014 0.2474 0.103 Uiso 1 1 calc R . . H20C H 0.6182 0.2714 0.3049 0.103 Uiso 1 1 calc R . . Br3 Br 0.14313(8) 0.26012(3) 0.07588(3) 0.04095(15) Uani 1 1 d . . . O4 O 0.4105(7) 0.4606(3) 1.0026(2) 0.0661(14) Uiso 1 1 d . . . C21 C 0.3238(11) 0.4206(5) 0.9574(3) 0.065(2) Uiso 1 1 d . . . H21A H 0.2060 0.4268 0.9620 0.078 Uiso 1 1 calc R . . H21B H 0.3502 0.3639 0.9567 0.078 Uiso 1 1 calc R . . C22 C 0.3803(16) 0.4597(7) 0.9057(5) 0.098(3) Uiso 1 1 d . . . H22A H 0.2942 0.4615 0.8768 0.117 Uiso 1 1 calc R . . H22B H 0.4752 0.4324 0.8897 0.117 Uiso 1 1 calc R . . C23 C 0.4246(18) 0.5427(8) 0.9258(5) 0.113(4) Uiso 1 1 d . . . H23A H 0.5318 0.5580 0.9112 0.135 Uiso 1 1 calc R . . H23B H 0.3442 0.5813 0.9123 0.135 Uiso 1 1 calc R . . C24 C 0.4261(12) 0.5404(5) 0.9833(3) 0.067(2) Uiso 1 1 d . . . H24A H 0.3361 0.5723 0.9983 0.081 Uiso 1 1 calc R . . H24B H 0.5282 0.5630 0.9975 0.081 Uiso 1 1 calc R . . O5 O 0.6837(7) 0.3702(3) 0.1423(2) 0.0591(13) Uiso 1 1 d . . . O6A O -0.0653(9) 0.4232(4) 0.0687(3) 0.0464(16) Uiso 0.65 1 d P A 1 O7A O 0.7496(11) 0.4165(5) -0.0248(3) 0.0630(19) Uiso 0.65 1 d P B 1 O8A O 0.5370(10) 0.2758(5) 0.0553(3) 0.0576(19) Uiso 0.65 1 d P C 1 O6B O -0.0268(16) 0.4348(7) 0.0412(5) 0.041(3) Uiso 0.35 1 d P D 2 O7B O 0.6620(19) 0.3763(8) 0.0293(6) 0.057(3) Uiso 0.35 1 d P E 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 In1 0.02579(17) 0.02414(14) 0.03223(16) -0.00394(13) 0.00021(14) -0.00131(13) Br1 0.0308(3) 0.0441(3) 0.0374(3) -0.0004(2) 0.0018(2) -0.0103(2) Br2 0.0340(3) 0.0303(3) 0.0576(3) 0.0041(2) 0.0048(3) -0.0063(2) O1 0.032(2) 0.0348(18) 0.0318(18) -0.0041(15) -0.0017(15) 0.0012(16) O2 0.030(2) 0.042(2) 0.035(2) -0.0023(17) -0.0009(16) 0.0046(16) O3 0.039(2) 0.0307(19) 0.042(2) -0.0130(16) 0.0026(18) -0.0026(17) N1 0.026(2) 0.027(2) 0.028(2) -0.0011(16) 0.0012(17) -0.0010(17) N2 0.028(2) 0.029(2) 0.028(2) 0.0032(16) -0.0028(17) -0.0049(17) C1 0.027(2) 0.020(2) 0.032(2) 0.0033(19) 0.002(2) 0.0000(17) C2 0.032(3) 0.028(2) 0.041(3) 0.004(2) 0.009(2) 0.006(2) C3 0.043(3) 0.028(2) 0.041(3) -0.003(2) 0.013(3) 0.002(2) C4 0.045(3) 0.023(2) 0.034(3) -0.0036(19) 0.007(2) -0.004(2) C5 0.041(3) 0.025(2) 0.029(2) -0.0026(19) 0.007(2) -0.005(2) C6 0.041(3) 0.020(2) 0.029(2) 0.0011(18) 0.001(2) -0.001(2) C7 0.050(3) 0.029(3) 0.039(3) 0.000(2) -0.007(3) -0.004(2) C8 0.060(4) 0.036(3) 0.043(3) 0.000(2) -0.017(3) -0.012(3) C9 0.044(3) 0.042(3) 0.042(3) 0.006(3) -0.015(3) -0.004(3) C10 0.036(3) 0.030(3) 0.036(3) 0.008(2) -0.008(2) -0.002(2) C11 0.028(3) 0.026(2) 0.035(3) -0.003(2) -0.003(2) 0.001(2) C12 0.033(3) 0.036(3) 0.034(3) -0.001(2) -0.001(2) -0.001(2) C13 0.051(4) 0.059(4) 0.049(4) 0.017(3) 0.002(3) -0.006(3) C14 0.050(4) 0.039(3) 0.052(3) 0.016(3) 0.002(3) 0.005(3) C15 0.072(5) 0.067(4) 0.034(3) -0.004(3) -0.009(3) 0.002(4) C16 0.032(3) 0.038(3) 0.042(3) 0.004(2) 0.004(2) 0.002(2) C17 0.044(4) 0.037(3) 0.046(3) 0.006(2) 0.005(3) 0.009(3) C18 0.048(4) 0.054(4) 0.074(5) 0.027(4) 0.011(3) 0.000(3) C19 0.069(5) 0.062(4) 0.051(4) 0.015(3) -0.011(3) 0.017(4) C20 0.106(7) 0.043(4) 0.055(4) 0.006(3) 0.003(5) 0.024(4) Br3 0.0488(4) 0.0308(3) 0.0433(3) -0.0025(2) -0.0012(3) 0.0001(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 In1 O3 2.239(4) . ? In1 O2 2.299(4) . ? In1 N2 2.306(4) . ? In1 N1 2.308(4) . ? In1 O1 2.318(4) . ? In1 Br2 2.5762(7) . ? In1 Br1 2.5822(6) . ? O1 C11 1.431(6) . ? O2 C16 1.438(7) . ? N1 C1 1.330(7) . ? N1 C5 1.358(6) . ? N2 C10 1.327(7) . ? N2 C6 1.350(6) . ? C1 C2 1.392(7) . ? C1 C11 1.520(7) . ? C2 C3 1.389(8) . ? C3 C4 1.400(9) . ? C4 C5 1.371(8) . ? C5 C6 1.481(8) . ? C6 C7 1.387(8) . ? C7 C8 1.374(10) . ? C8 C9 1.389(9) . ? C9 C10 1.387(8) . ? C10 C16 1.512(8) . ? C11 C12 1.555(7) . ? C12 C13 1.514(9) . ? C12 C14 1.535(9) . ? C12 C15 1.542(8) . ? C16 C17 1.569(8) . ? C17 C19 1.515(10) . ? C17 C20 1.521(9) . ? C17 C18 1.535(10) . ? O4 C24 1.440(10) . ? O4 C21 1.458(10) . ? C21 C22 1.469(13) . ? C22 C23 1.537(17) . ? C23 C24 1.359(14) . ? 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 O3 In1 O2 75.49(15) . . ? O3 In1 N2 143.46(16) . . ? O2 In1 N2 68.34(15) . . ? O3 In1 N1 144.67(16) . . ? O2 In1 N1 139.82(15) . . ? N2 In1 N1 71.72(15) . . ? O3 In1 O1 76.56(15) . . ? O2 In1 O1 152.05(14) . . ? N2 In1 O1 139.48(14) . . ? N1 In1 O1 68.12(14) . . ? O3 In1 Br2 89.58(12) . . ? O2 In1 Br2 91.98(10) . . ? N2 In1 Br2 96.53(10) . . ? N1 In1 Br2 88.25(11) . . ? O1 In1 Br2 87.58(10) . . ? O3 In1 Br1 86.58(12) . . ? O2 In1 Br1 87.05(10) . . ? N2 In1 Br1 86.56(11) . . ? N1 In1 Br1 94.89(11) . . ? O1 In1 Br1 91.54(10) . . ? Br2 In1 Br1 176.17(2) . . ? C11 O1 In1 122.9(3) . . ? C16 O2 In1 123.2(3) . . ? C1 N1 C5 120.5(5) . . ? C1 N1 In1 120.7(3) . . ? C5 N1 In1 116.4(4) . . ? C10 N2 C6 121.4(5) . . ? C10 N2 In1 119.8(4) . . ? C6 N2 In1 116.6(3) . . ? N1 C1 C2 120.3(5) . . ? N1 C1 C11 117.1(4) . . ? C2 C1 C11 122.5(5) . . ? C3 C2 C1 120.0(6) . . ? C2 C3 C4 118.4(5) . . ? C5 C4 C3 119.0(5) . . ? N1 C5 C4 121.5(6) . . ? N1 C5 C6 115.4(5) . . ? C4 C5 C6 123.0(5) . . ? N2 C6 C7 120.6(5) . . ? N2 C6 C5 116.1(4) . . ? C7 C6 C5 123.3(5) . . ? C8 C7 C6 118.5(5) . . ? C7 C8 C9 120.0(6) . . ? C10 C9 C8 119.0(6) . . ? N2 C10 C9 120.1(5) . . ? N2 C10 C16 118.2(5) . . ? C9 C10 C16 121.7(5) . . ? O1 C11 C1 108.0(4) . . ? O1 C11 C12 109.5(4) . . ? C1 C11 C12 113.9(4) . . ? C13 C12 C14 109.0(5) . . ? C13 C12 C15 110.7(6) . . ? C14 C12 C15 107.6(6) . . ? C13 C12 C11 110.5(5) . . ? C14 C12 C11 111.9(5) . . ? C15 C12 C11 107.0(5) . . ? O2 C16 C10 107.2(5) . . ? O2 C16 C17 109.9(5) . . ? C10 C16 C17 113.4(5) . . ? C19 C17 C20 108.7(6) . . ? C19 C17 C18 109.5(6) . . ? C20 C17 C18 109.3(6) . . ? C19 C17 C16 110.5(5) . . ? C20 C17 C16 108.3(5) . . ? C18 C17 C16 110.5(5) . . ? C24 O4 C21 104.7(6) . . ? O4 C21 C22 103.9(8) . . ? C21 C22 C23 103.6(9) . . ? C24 C23 C22 106.6(11) . . ? C23 C24 O4 110.1(8) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.733 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.099