Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_1 _database_code_CSD 167809 _audit_creation_date '19101-08-21' _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; #------------------------------------------------------------------------------ _journal_coden_Cambridge 182 loop_ _publ_author_name 'Metzner, Patrick' 'Philouze, Christian' 'Takada, Hiroya' _publ_requested_journal 'Chemical Communications' _publ_requested_category ? _publ_contact_author_name 'Dr Patrick Metzner' _publ_contact_author_address ; Laboratoire de Chimie Moleculaire et Thio-orgaique (UMR CNRS 6507) ISMRA-Universite 6, Boulevard du Marechal Juin 14050 Caen FRANCE ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' +33 231 452 885' _publ_contact_author_fax ' +33 231 452 877' _publ_contact_author_email 'metzner@ismra.fr' loop_ _publ_section_references ; Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. ; _publ_section_title ; First chiral selenium ylides used for asymmetric conversion of aldehydes into epoxides ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 9.009(3) _cell_length_b 9.009(3) _cell_length_c 12.21(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 991.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293.2 _cell_measurement_reflns_used 21 _cell_measurement_theta_min 10.4 _cell_measurement_theta_max 12.2 #------------------------------------------------------------------------------ _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 43 21 2 ' _symmetry_Int_Tables_number 96 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' '1/2-y,1/2+x,3/4+z' '1/2+y,1/2-x,1/4+z' ' +y, +x, -z' ' -y, -x,1/2-z' '1/2-x,1/2+y,3/4-z' '1/2+x,1/2-y,1/4-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 2.164 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 161.46 _chemical_formula_analytical ? _chemical_formula_sum 'C3 H6 Br Se0.50 ' _chemical_formula_moiety 'C3 H6 Br Se0.50 ' _chemical_formula_structural ? _chemical_compound_source synthesis _exptl_crystal_F_000 608.00 _exptl_absorpt_coefficient_mu 11.806 _exptl_absorpt_correction_type XABS _exptl_absorpt_correction_T_max 1.972 _exptl_absorpt_correction_T_min 0.510 _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'CAD-4' _diffrn_measurement_method \w _diffrn_standards_number 2 _diffrn_standards_interval_count 120 _diffrn_standards_decay_% 3.08 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 5 0 2 0 5 2 _diffrn_reflns_number 6033 _reflns_number_total 911 _reflns_number_gt 436 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.1786 _diffrn_reflns_av_sigmaI/netI 0.070 _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 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 29.97 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.06280 _diffrn_orient_matrix_UB_12 0.06047 _diffrn_orient_matrix_UB_13 -0.05066 _diffrn_orient_matrix_UB_21 0.06335 _diffrn_orient_matrix_UB_22 -0.08883 _diffrn_orient_matrix_UB_23 -0.01495 _diffrn_orient_matrix_UB_31 -0.06605 _diffrn_orient_matrix_UB_32 -0.02780 _diffrn_orient_matrix_UB_33 -0.06252 #------------------------------------------------------------------------------ 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 Se 0 4 -0.178 2.223 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Br 0 8 -0.374 2.456 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; C 0 24 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 48 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #------------------------------------------------------------------------------ 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_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom Br(5) -0.61111(9) 0.7970(1) -0.93656(7) 0.0731(2) 1.000 . Uani d ? Se(1) -0.69780(8) 0.6978 -0.7500 0.0506(1) 0.500 ST Uani d ? C(2) -0.6876(7) 0.4844(8) -0.7983(6) 0.060(2) 1.000 . Uani d ? C(3) -0.5212(9) 0.4526(8) -0.7986(7) 0.073(2) 1.000 . Uani d ? C(4) -0.7717(8) 0.4556(9) -0.9058(6) 0.078(3) 1.000 . Uani d ? H(1) -0.7318 0.4253 -0.7428 0.072 1.000 . Uiso c ? H(2) -0.5050 0.3505 -0.8139 0.087 1.000 . Uiso c ? H(3) -0.4743 0.5114 -0.8531 0.087 1.000 . Uiso c ? H(4) -0.7610 0.3543 -0.9259 0.094 1.000 . Uiso c ? H(5) -0.7321 0.5169 -0.9620 0.094 1.000 . Uiso c ? H(6) -0.8739 0.4777 -0.8959 0.094 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 Br(5) 0.0598(4) 0.0887(5) 0.0708(4) -0.0074(6) -0.0070(5) 0.0248(6) Se(1) 0.0443(3) 0.0443 0.0634(6) 0.0018(6) 0.0041 0.0041(4) C(2) 0.054(4) 0.043(3) 0.082(5) 0.006(4) 0.023(5) 0.008(5) C(3) 0.075(5) 0.048(4) 0.095(6) 0.014(5) 0.025(6) 0.004(5) C(4) 0.084(5) 0.072(4) 0.080(6) 0.000(6) 0.010(6) -0.018(5) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00004|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 436 _refine_ls_number_parameters 42 _refine_ls_number_restraints 0 _refine_ls_number_constraints 3 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_all 0.0358 _refine_ls_wR_factor_ref 0.0358 _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_shift/su_max 0.0040 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_min -1.81 _refine_diff_density_max 0.76 #------------------------------------------------------------------------------ _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 BR5 SE1 2.57 . . no SE1 C2 2.013(7) . . yes SE1 C2 2.013(7) . 6_553 yes SE1 H1 2.48 . . no SE1 H1 2.48 . 6_553 no C2 C3 1.53(1) . . yes C2 C3 2.447(9) . 6_553 yes C2 C4 1.54(1) . . yes C2 H1 0.95 . . no C2 H2 2.05 . . no C2 H3 2.05 . . no C2 H3 2.44 . 6_553 no C2 H4 2.06 . . no C2 H5 2.06 . . no C2 H6 2.06 . . no C3 C3 1.47(2) . 6_553 yes C3 H1 2.03 . . no C3 H2 0.95 . . no C3 H2 2.11 . 6_553 no C3 H3 0.95 . . no C3 H3 1.86 . 6_553 no C4 H1 2.04 . . no C4 H4 0.95 . . no C4 H5 0.95 . . no C4 H6 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 BR5 SE1 BR5 176.4 . . 6_553 no BR5 SE1 C2 93.4 . . . no BR5 SE1 C2 89.2 . . 6_553 no BR5 SE1 H1 114.5 . . . no BR5 SE1 H1 67.9 . . 6_553 no BR5 SE1 C2 89.2 6_553 . . no BR5 SE1 C2 93.4 6_553 . 6_553 no BR5 SE1 H1 67.9 6_553 . . no BR5 SE1 H1 114.5 6_553 . 6_553 no C2 SE1 C2 89.9(4) . . 6_553 yes C2 SE1 H1 21.4 . . . no C2 SE1 H1 93.6 . . 6_553 no C2 SE1 H1 93.6 6_553 . . no C2 SE1 H1 21.4 6_553 . 6_553 no H1 SE1 H1 104.3 . . 6_553 no SE1 C2 C3 103.0(5) . . . yes SE1 C2 C3 76.6(3) . . 6_553 yes SE1 C2 C4 112.9(5) . . . yes SE1 C2 H1 107.9 . . . no SE1 C2 H2 128.8 . . . no SE1 C2 H3 91.5 . . . no SE1 C2 H3 81.0 . . 6_553 no SE1 C2 H4 138.7 . . . no SE1 C2 H5 98.0 . . . no SE1 C2 H6 99.2 . . . no C3 C2 C3 34.6(5) . . 6_553 yes C3 C2 C4 116.8(7) . . . yes C3 C2 H1 107.9 . . . no C3 C2 H2 25.9 . . . no C3 C2 H3 25.9 . . . no C3 C2 H3 49.9 . . 6_553 no C3 C2 H4 101.9 . . . no C3 C2 H5 102.5 . . . no C3 C2 H6 142.5 . . . no C3 C2 C4 149.5(5) 6_553 . . yes C3 C2 H1 95.4 6_553 . . no C3 C2 H2 55.3 6_553 . . no C3 C2 H3 48.0 6_553 . . no C3 C2 H3 22.4 6_553 . 6_553 no C3 C2 H4 136.1 6_553 . . no C3 C2 H5 128.2 6_553 . . no C3 C2 H6 171.3 6_553 . . no C4 C2 H1 107.9 . . . no C4 C2 H2 102.5 . . . no C4 C2 H3 101.7 . . . no C4 C2 H3 164.1 . . 6_553 no C4 C2 H4 25.8 . . . no C4 C2 H5 25.8 . . . no C4 C2 H6 25.8 . . . no H1 C2 H2 94.1 . . . no H1 C2 H3 133.8 . . . no H1 C2 H3 73.2 . . 6_553 no H1 C2 H4 94.9 . . . no H1 C2 H5 133.7 . . . no H1 C2 H6 93.1 . . . no H2 C2 H3 44.5 . . . no H2 C2 H3 61.7 . . 6_553 no H2 C2 H4 81.5 . . . no H2 C2 H5 98.6 . . . no H2 C2 H6 125.7 . . . no H3 C2 H3 69.0 . . 6_553 no H3 C2 H4 97.0 . . . no H3 C2 H5 81.3 . . . no H3 C2 H6 125.3 . . . no H3 C2 H4 139.6 6_553 . . no H3 C2 H5 150.2 6_553 . . no H3 C2 H6 165.5 6_553 . . no H4 C2 H5 44.3 . . . no H4 C2 H6 44.3 . . . no H5 C2 H6 44.3 . . . no C2 C3 C2 88.2(6) . . 6_553 yes C2 C3 C3 109.3(6) . . 6_553 yes C2 C3 H1 26.4 . . . no C2 C3 H2 109.5 . . . no C2 C3 H2 132.1 . . 6_553 no C2 C3 H3 109.5 . . . no C2 C3 H3 91.4 . . 6_553 no C2 C3 C3 36.1(3) 6_553 . 6_553 yes C2 C3 H1 94.0 6_553 . . no C2 C3 H2 155.8 6_553 . . no C2 C3 H2 52.8 6_553 . 6_553 no C2 C3 H3 78.3 6_553 . . no C2 C3 H3 54.8 6_553 . 6_553 no C3 C3 H1 99.9 6_553 . . no C3 C3 H2 120.0 6_553 . . no C3 C3 H2 22.9 6_553 . 6_553 no C3 C3 H3 98.3 6_553 . . no C3 C3 H3 30.3 6_553 . 6_553 no H1 C3 H2 95.3 . . . no H1 C3 H2 119.2 . . 6_553 no H1 C3 H3 135.9 . . . no H1 C3 H3 73.9 . . 6_553 no H2 C3 H2 103.4 . . 6_553 no H2 C3 H3 109.5 . . . no H2 C3 H3 106.8 . . 6_553 no H2 C3 H3 90.5 6_553 . . no H2 C3 H3 45.4 6_553 . 6_553 no H3 C3 H3 128.1 . . 6_553 no C2 C4 H1 26.3 . . . no C2 C4 H4 109.5 . . . no C2 C4 H5 109.5 . . . no C2 C4 H6 109.5 . . . no H1 C4 H4 96.1 . . . no H1 C4 H5 135.7 . . . no H1 C4 H6 94.3 . . . no H4 C4 H5 109.5 . . . no H4 C4 H6 109.5 . . . no H5 C4 H6 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag BR5 SE1 C2 C3 . . . . 75.2(5) no BR5 SE1 C2 C3 . . . 6_553 97.8(2) no BR5 SE1 C2 C4 . . . . -51.6(5) no BR5 SE1 C2 C3 . . 6_553 6_553 -107.3(5) no BR5 SE1 C2 C4 . . 6_553 6_553 125.9(5) no SE1 C2 C3 C2 . . . 6_553 11.4(3) no SE1 C2 C3 C3 . . . 6_553 41.2(9) no SE1 C2 C3 C2 . . 6_553 6_553 -11.5(3) no SE1 C2 C3 C3 . . 6_553 . -138.7(9) no SE1 C2 C3 C3 . 6_553 6_553 . 41.2(9) no C2 SE1 C2 C3 . . 6_553 6_553 -14.0(4) no C2 SE1 C2 C4 . . 6_553 6_553 -140.8(6) no C2 C3 C2 C3 . . 6_553 6_553 127(1) no C2 C3 C2 C4 . . 6_553 6_553 101(1) no C2 C3 C3 C2 . . 6_553 6_553 -57(1) no C2 C3 C2 C4 . 6_553 6_553 6_553 135.7(6) no C2 C3 C3 C2 . 6_553 . 6_553 57(1) no C3 C2 C3 C2 . . 6_553 6_553 127(1) no C3 C3 C2 C4 . 6_553 6_553 6_553 165.5(7) no #------------------------------------------------------------------------------