Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_katagiri_3 _database_code_CSD 169307 _journal_coden_Cambridge 182 _publ_requested_journal ' Chemical Communications' _publ_contact_author 'Dr Kenji Uneyama' _publ_contact_author_address ; Dr Kenji Uneyama Department of Applied Chemistry Okayama University Faculty of Engineering Tsushimanaka 3-1-1 Okayama 700-8530 JAPAN ; _publ_contact_author_email 'TKATA@CC.OKAYAMA-U.AC.JP ' loop_ _publ_author_name _publ_author_address 'Handa, Michiharu' ; ? ; 'Irie, Minoru' ; ? ; 'Katagiri, Toshimasa' ; Department of Chemistry, Faculty of Engineering, Okayama University, Tsushimanaka 3-1-1, Okayama, 700-8530, Japan ; 'Uneyama, Kenji' ; ? ; 'Yamaji, Sachiko' ; ? ; _publ_section_title ; Diastereoselectivity Controlled by Electostatic Repulsion between Negative Charge on Trifluoromethyl Group and That on Aromatic Rings ; #------------------------------------------------------------------------------ _audit_creation_date 'Mon Aug 28 17:20:05 2001' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution ? _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 301.14 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H3 F8 N ' _chemical_formula_moiety 'C11 H3 F8 N ' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 10.6401(4) _cell_length_b 10.6401(4) _cell_length_c 10.6401(4) _cell_angle_alpha 111.8530(4) _cell_angle_beta 111.8530(4) _cell_angle_gamma 111.8530(4) _cell_volume 835.60(6) _cell_formula_units_Z 3 _cell_measurement_temperature 150.2 _cell_measurement_reflns_used 6053 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 #------------------------------------------------------------------------------ _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M 'R 3' _symmetry_Int_Tables_number 146 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z z,x,y y,z,x _exptl_crystal_description 'needle' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 1.000 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 444.00 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 150.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'Imaging Plate' _diffrn_measurement_device 'Rigaku RAXIS-IV' _diffrn_measurement_method ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h ? _diffrn_standard_refln_index_k ? _diffrn_standard_refln_index_l ? _diffrn_reflns_number 1281 _reflns_number_total 1281 _reflns_number_observed 1236 _reflns_observed_criterion >0.8sigma(I) _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.058 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 54.90 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.03643 _diffrn_orient_matrix_UB_12 0.04003 _diffrn_orient_matrix_UB_13 0.07077 _diffrn_orient_matrix_UB_21 -0.03176 _diffrn_orient_matrix_UB_22 -0.09914 _diffrn_orient_matrix_UB_23 0.00337 _diffrn_orient_matrix_UB_31 0.11609 _diffrn_orient_matrix_UB_32 0.06620 _diffrn_orient_matrix_UB_33 0.10389 #------------------------------------------------------------------------------ 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 33 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 9 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; F 0 24 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N 0 3 0.006 0.003 ;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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_refinement_flags F(1) 0.7539 0.3504 0.2188 0.0305(5) Uani d . 1.00 S F(2) 0.8901(3) 0.6086(3) 0.5247(3) 0.0405(5) Uani d . 1.00 . F(3) 0.7824(3) 0.5592(3) 0.7090(3) 0.0441(6) Uani d . 1.00 . F(4) 0.5498(3) 0.2436(3) 0.5902(3) 0.0398(6) Uani d . 1.00 . F(5) 0.4075(3) -0.0189(3) 0.2788(3) 0.0262(5) Uani d . 1.00 . F(6) 0.3280(3) 0.1775(3) 0.0361(3) 0.0331(5) Uani d . 1.00 . F(7) 0.1520(3) -0.0348(3) 0.0090(3) 0.0401(7) Uani d . 1.00 . F(8) 0.1035(3) -0.0390(3) -0.2081(3) 0.0327(5) Uani d . 1.00 . N(1) 0.5322(4) -0.2148(4) 0.0742(4) 0.0282(7) Uani d . 1.00 . C(1) 0.4864(4) 0.0062(4) 0.0640(4) 0.0176(7) Uani d . 1.00(1) . C(2) 0.4609(4) 0.0147(4) -0.0822(4) 0.0240(8) Uani d . 1.02(1) . C(3) 0.3105(4) -0.0711(4) -0.0852(4) 0.0199(8) Uani d . 1.02(1) . C(4) 0.5711(4) 0.1570(4) 0.2358(4) 0.0201(8) Uani d . 1.04(1) . C(5) 0.5250(4) 0.1361(4) 0.3373(4) 0.0198(7) Uani d . 1.00(1) . C(6) 0.5951(4) 0.2690(4) 0.4951(4) 0.0263(8) Uani d . 1.00(1) . C(7) 0.7166(5) 0.4297(5) 0.5571(4) 0.0291(8) Uani d . 1.00 . C(8) 0.7688(4) 0.4546(4) 0.4631(4) 0.0277(7) Uani d . 1.00 . C(9) 0.6975(4) 0.3196(4) 0.3047(4) 0.0218(7) Uani d . 1.00 . C(10) 0.2244(4) 0.0086(4) -0.0611(4) 0.0219(7) Uani d . 1.00 . C(11) 0.5116(4) -0.1181(4) 0.0679(4) 0.0205(7) Uani d . 1.00 . H(1) 0.229(5) -0.198(5) -0.163(5) 0.037(10) Uiso calc . 1.00 . H(2) 0.494(4) 0.131(5) -0.058(4) 0.031(9) Uiso calc . 1.00 . H(3) 0.479(4) -0.058(5) -0.160(4) 0.032(9) Uiso calc . 1.00 . 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 F(1) 0.0274(10) 0.0269(9) 0.035(1) 0.0114(7) 0.0189(8) 0.0208(8) F(2) 0.030(1) 0.0165(9) 0.038(1) 0.0059(8) 0.0058(9) 0.0103(8) F(3) 0.047(1) 0.036(1) 0.0193(9) 0.026(1) 0.0093(9) 0.0023(8) F(4) 0.047(1) 0.057(1) 0.0257(10) 0.035(1) 0.0269(9) 0.0235(9) F(5) 0.0281(10) 0.0266(9) 0.0322(10) 0.0152(8) 0.0216(8) 0.0208(8) F(6) 0.0306(10) 0.0208(9) 0.031(1) 0.0174(8) 0.0095(8) 0.0098(8) F(7) 0.052(1) 0.065(1) 0.059(1) 0.048(1) 0.049(1) 0.051(1) F(8) 0.0287(10) 0.038(1) 0.0216(9) 0.0224(9) 0.0078(8) 0.0150(9) N(1) 0.028(1) 0.026(1) 0.027(1) 0.018(1) 0.014(1) 0.013(1) C(1) 0.017(1) 0.018(1) 0.018(1) 0.012(1) 0.010(1) 0.010(1) C(2) 0.024(2) 0.028(2) 0.024(2) 0.015(1) 0.017(1) 0.016(1) C(3) 0.020(2) 0.020(2) 0.018(2) 0.011(1) 0.011(1) 0.011(1) C(4) 0.022(2) 0.020(1) 0.021(2) 0.013(1) 0.013(1) 0.013(1) C(5) 0.020(1) 0.023(1) 0.022(1) 0.016(1) 0.013(1) 0.014(1) C(6) 0.027(2) 0.034(2) 0.019(2) 0.021(1) 0.013(1) 0.015(1) C(7) 0.029(2) 0.026(2) 0.016(1) 0.020(1) 0.005(1) 0.005(1) C(8) 0.023(1) 0.016(1) 0.024(2) 0.009(1) 0.004(1) 0.008(1) C(9) 0.019(1) 0.025(2) 0.025(1) 0.013(1) 0.013(1) 0.017(1) C(10) 0.025(1) 0.023(1) 0.019(1) 0.015(1) 0.012(1) 0.014(1) C(11) 0.019(1) 0.019(1) 0.021(1) 0.011(1) 0.013(1) 0.009(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1236 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0321 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0308 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.411 _refine_ls_shift/esd_max 0.0030 _refine_ls_shift/esd_mean 0.0010 _refine_diff_density_min -0.27 _refine_diff_density_max 0.19 #------------------------------------------------------------------------------ _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 F(1) C(9) 1.338(3) 1_555 1_555 yes F(2) C(8) 1.333(3) 1_555 1_555 yes F(3) C(7) 1.335(4) 1_555 1_555 yes F(4) C(6) 1.341(4) 1_555 1_555 yes F(5) C(5) 1.339(3) 1_555 1_555 yes F(6) C(10) 1.344(3) 1_555 1_555 yes F(7) C(10) 1.334(4) 1_555 1_555 yes F(8) C(10) 1.336(3) 1_555 1_555 yes N(1) C(11) 1.148(4) 1_555 1_555 yes C(1) C(2) 1.520(4) 1_555 1_555 yes C(1) C(3) 1.540(4) 1_555 1_555 yes C(1) C(4) 1.497(4) 1_555 1_555 yes C(1) C(11) 1.456(4) 1_555 1_555 yes C(2) C(3) 1.500(4) 1_555 1_555 yes C(3) C(10) 1.489(4) 1_555 1_555 yes C(4) C(5) 1.396(4) 1_555 1_555 yes C(4) C(9) 1.388(4) 1_555 1_555 yes C(5) C(6) 1.375(4) 1_555 1_555 yes C(6) C(7) 1.382(5) 1_555 1_555 yes C(7) C(8) 1.372(5) 1_555 1_555 yes C(8) C(9) 1.383(4) 1_555 1_555 yes #------------------------------------------------------------------------------ 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 C(2) C(1) C(3) 58.7(2) 1_555 1_555 1_555 yes C(2) C(1) C(4) 122.9(2) 1_555 1_555 1_555 yes C(2) C(1) C(11) 117.1(2) 1_555 1_555 1_555 yes C(3) C(1) C(4) 121.4(2) 1_555 1_555 1_555 yes C(3) C(1) C(11) 113.7(2) 1_555 1_555 1_555 yes C(4) C(1) C(11) 112.8(2) 1_555 1_555 1_555 yes C(1) C(2) C(3) 61.3(2) 1_555 1_555 1_555 yes C(1) C(2) H(2) 114(1) 1_555 1_555 1_555 no C(1) C(2) H(3) 115(2) 1_555 1_555 1_555 no C(3) C(2) H(2) 111(2) 1_555 1_555 1_555 no C(3) C(2) H(3) 118(1) 1_555 1_555 1_555 no H(2) C(2) H(3) 120(2) 1_555 1_555 1_555 no C(1) C(3) C(2) 60.0(2) 1_555 1_555 1_555 yes C(1) C(3) C(10) 119.8(2) 1_555 1_555 1_555 yes C(1) C(3) H(1) 116(2) 1_555 1_555 1_555 no C(2) C(3) C(10) 120.1(3) 1_555 1_555 1_555 yes C(2) C(3) H(1) 119(2) 1_555 1_555 1_555 no C(10) C(3) H(1) 111(2) 1_555 1_555 1_555 no C(1) C(4) C(5) 119.2(2) 1_555 1_555 1_555 yes C(1) C(4) C(9) 124.3(3) 1_555 1_555 1_555 yes C(5) C(4) C(9) 116.5(3) 1_555 1_555 1_555 yes F(5) C(5) C(4) 118.9(3) 1_555 1_555 1_555 yes F(5) C(5) C(6) 118.6(3) 1_555 1_555 1_555 yes C(4) C(5) C(6) 122.5(3) 1_555 1_555 1_555 yes F(4) C(6) C(5) 120.8(3) 1_555 1_555 1_555 yes F(4) C(6) C(7) 120.0(3) 1_555 1_555 1_555 yes C(5) C(6) C(7) 119.2(3) 1_555 1_555 1_555 yes F(3) C(7) C(6) 119.3(3) 1_555 1_555 1_555 yes F(3) C(7) C(8) 120.8(3) 1_555 1_555 1_555 yes C(6) C(7) C(8) 119.9(3) 1_555 1_555 1_555 yes F(2) C(8) C(7) 120.2(3) 1_555 1_555 1_555 yes F(2) C(8) C(9) 119.7(3) 1_555 1_555 1_555 yes C(7) C(8) C(9) 120.1(3) 1_555 1_555 1_555 yes F(1) C(9) C(4) 120.6(2) 1_555 1_555 1_555 yes F(1) C(9) C(8) 117.8(3) 1_555 1_555 1_555 yes C(4) C(9) C(8) 121.6(3) 1_555 1_555 1_555 yes F(6) C(10) F(7) 107.3(3) 1_555 1_555 1_555 yes F(6) C(10) F(8) 106.2(2) 1_555 1_555 1_555 yes F(6) C(10) C(3) 113.3(2) 1_555 1_555 1_555 yes F(7) C(10) F(8) 107.2(2) 1_555 1_555 1_555 yes F(7) C(10) C(3) 111.5(2) 1_555 1_555 1_555 yes F(8) C(10) C(3) 111.0(2) 1_555 1_555 1_555 yes N(1) C(11) C(1) 178.6(3) 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ 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 F(1) F(5) 3.057(2) 1_555 3_655 ? F(1) F(4) 3.206(2) 1_555 2_555 ? F(1) F(6) 3.272(2) 1_555 2_655 ? F(1) F(8) 3.293(2) 1_555 2_655 ? F(1) C(2) 3.513(3) 1_555 2_655 ? F(2) F(8) 2.867(2) 1_555 1_666 ? F(2) F(4) 3.088(3) 1_555 2_555 ? F(2) F(3) 3.153(3) 1_555 2_555 ? F(2) N(1) 3.317(3) 1_555 2_656 ? F(2) C(2) 3.482(4) 1_555 3_665 ? F(3) N(1) 3.057(4) 1_555 2_656 ? F(3) F(8) 3.191(3) 1_555 3_666 ? F(3) C(11) 3.248(4) 1_555 2_656 ? F(3) F(7) 3.473(3) 1_555 1_666 ? F(3) F(3) 3.473(4) 1_555 2_555 ? F(3) F(3) 3.473(4) 1_555 3_555 ? F(4) F(6) 3.005(3) 1_555 3_555 ? F(4) C(8) 3.159(4) 1_555 3_555 ? F(4) C(9) 3.231(4) 1_555 3_555 ? F(5) F(6) 2.898(3) 1_555 3_555 ? F(5) C(9) 3.059(3) 1_555 2_545 ? F(5) N(1) 3.374(3) 1_555 3_655 ? F(5) C(4) 3.484(3) 1_555 2_545 ? F(5) C(8) 3.502(4) 1_555 2_545 ? F(6) F(7) 3.069(3) 1_555 2_555 ? F(6) C(5) 3.396(3) 1_555 2_555 ? F(6) C(6) 3.419(4) 1_555 2_555 ? F(7) F(8) 2.941(3) 1_555 3_555 ? F(7) F(7) 2.983(3) 1_555 2_555 ? F(7) F(7) 2.983(3) 1_555 3_555 ? F(7) C(10) 3.228(4) 1_555 3_555 ? F(8) C(2) 3.082(4) 1_555 3_554 ? N(1) C(7) 3.102(4) 1_555 3_544 ? N(1) C(5) 3.241(4) 1_555 2_545 ? N(1) C(8) 3.255(4) 1_555 3_544 ? N(1) C(3) 3.351(4) 1_555 3_655 ? N(1) C(6) 3.417(4) 1_555 2_545 ? N(1) C(11) 3.592(4) 1_555 3_655 ? C(7) C(11) 3.520(4) 1_555 2_656 ? #-----------------------------------------