# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Norio Shibata' _publ_contact_author_email nozshiba@nitech.ac.jp loop_ _publ_author_name 'Kawai, Hiroyuki' 'Sugita, Yutaka' 'Tokunaga, Etsuko' 'Sato, Hiroyasu' 'Shiro, Motoo' 'Shibata, Norio' data_SUY-330 _database_code_depnum_ccdc_archive 'CCDC 866497' #TrackingRef 'CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H12 F3 N O2' _chemical_formula_moiety 'C13 H12 F3 N O2' _chemical_formula_weight 271.24 _chemical_melting_point ? _chemical_absolute_configuration ad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 8.1200(19) _cell_length_b 5.4244(12) _cell_length_c 13.990(4) _cell_angle_alpha 90.0000 _cell_angle_beta 91.881(8) _cell_angle_gamma 90.0000 _cell_volume 615.9(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4265 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 68.15 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280.00 _exptl_absorpt_coefficient_mu 1.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.408 _exptl_absorpt_correction_T_max 0.894 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 6656 _diffrn_reflns_av_R_equivalents 0.1426 _diffrn_reflns_theta_max 68.24 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_max 0.956 _diffrn_measured_fraction_theta_full 0.956 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2142 _reflns_number_gt 816 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1506 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2142 _refine_ls_number_parameters 173 _refine_ls_goodness_of_fit_ref 0.810 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0001P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.180 _refine_diff_density_min -0.130 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 898 Friedel Pairs' _refine_ls_abs_structure_Flack -0.16(28) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F1 F 0.0704(4) 0.3554(7) 0.5543(3) 0.1093(12) Uani 1.0 2 d . . . F2 F -0.0816(4) 0.4598(7) 0.6698(3) 0.1037(11) Uani 1.0 2 d . . . F3 F -0.0211(4) 0.0805(6) 0.6501(2) 0.1003(11) Uani 1.0 2 d . . . O1 O 0.5242(5) 0.4496(9) 0.6576(3) 0.1024(13) Uani 1.0 2 d . . . O2 O 0.4566(5) 0.8423(6) 0.6211(3) 0.0928(12) Uani 1.0 2 d . . . N1 N 0.2827(5) 0.6949(10) 0.8018(4) 0.0881(14) Uani 1.0 2 d . . . C1 C 0.2341(7) 0.5273(12) 0.8582(5) 0.0859(17) Uani 1.0 2 d . . . C2 C 0.2609(7) 0.6083(11) 0.7035(5) 0.0869(17) Uani 1.0 2 d . . . C3 C 0.1903(7) 0.3394(10) 0.7078(5) 0.0892(17) Uani 1.0 2 d . . . C4 C 0.1619(7) 0.2960(10) 0.8134(5) 0.0992(19) Uani 1.0 2 d . . . C5 C 0.2495(7) 0.5613(12) 0.9639(5) 0.0901(17) Uani 1.0 2 d . . . C6 C 0.3385(6) 0.7587(11) 1.0049(5) 0.0875(17) Uani 1.0 2 d . . . C7 C 0.3585(7) 0.7813(12) 1.1028(5) 0.0919(17) Uani 1.0 2 d . . . C8 C 0.2936(8) 0.6108(13) 1.1638(5) 0.1010(19) Uani 1.0 2 d . . . C9 C 0.2050(7) 0.4082(13) 1.1255(5) 0.1004(19) Uani 1.0 2 d . . . C10 C 0.1827(6) 0.3854(12) 1.0266(5) 0.0927(18) Uani 1.0 2 d . . . C11 C 0.4294(7) 0.6217(12) 0.6583(4) 0.0862(17) Uani 1.0 2 d . . . C12 C 0.6191(6) 0.8720(11) 0.5825(4) 0.0929(18) Uani 1.0 2 d . . . C13 C 0.0409(8) 0.3111(13) 0.6463(5) 0.0966(19) Uani 1.0 2 d . . . H2 H 0.1811 0.7175 0.6676 0.1042 Uiso 1.0 2 calc R . . H3 H 0.2760 0.2214 0.6862 0.1070 Uiso 1.0 2 calc R . . H4A H 0.0431 0.2803 0.8259 0.1190 Uiso 1.0 2 calc R . . H4B H 0.2203 0.1468 0.8370 0.1190 Uiso 1.0 2 calc R . . H6 H 0.3857 0.8787 0.9646 0.1050 Uiso 1.0 2 calc R . . H7 H 0.4185 0.9175 1.1286 0.1103 Uiso 1.0 2 calc R . . H8 H 0.3082 0.6294 1.2311 0.1212 Uiso 1.0 2 calc R . . H9 H 0.1607 0.2879 1.1668 0.1204 Uiso 1.0 2 calc R . . H10 H 0.1218 0.2498 1.0010 0.1113 Uiso 1.0 2 calc R . . H12A H 0.7032 0.8327 0.6320 0.1114 Uiso 1.0 2 calc R . . H12B H 0.6331 1.0427 0.5613 0.1114 Uiso 1.0 2 calc R . . H12C H 0.6307 0.7605 0.5280 0.1114 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.107(3) 0.109(3) 0.112(3) -0.017(2) 0.0013(19) 0.002(3) F2 0.080(3) 0.085(3) 0.146(3) 0.010(2) 0.0100(18) 0.002(2) F3 0.081(3) 0.088(3) 0.132(3) -0.0138(19) -0.0010(18) -0.002(2) O1 0.088(3) 0.077(3) 0.143(4) 0.001(3) 0.014(3) 0.009(3) O2 0.076(3) 0.073(3) 0.129(3) -0.003(3) 0.009(2) 0.007(3) N1 0.065(3) 0.084(4) 0.116(4) -0.005(3) 0.006(3) -0.003(3) C1 0.073(4) 0.075(5) 0.111(5) 0.005(4) 0.008(4) 0.001(4) C2 0.074(4) 0.066(4) 0.122(5) -0.000(3) 0.014(4) -0.005(4) C3 0.076(4) 0.065(4) 0.126(5) -0.001(4) 0.004(4) 0.002(4) C4 0.089(4) 0.073(5) 0.135(6) -0.003(4) -0.003(4) -0.001(4) C5 0.068(4) 0.076(5) 0.126(5) -0.007(3) 0.005(4) -0.003(4) C6 0.069(4) 0.070(4) 0.124(5) 0.005(3) 0.002(4) -0.003(4) C7 0.076(4) 0.084(5) 0.115(5) -0.004(4) -0.000(4) -0.005(4) C8 0.092(5) 0.091(5) 0.121(5) 0.009(4) 0.013(4) -0.006(5) C9 0.088(5) 0.091(5) 0.122(6) -0.007(4) 0.019(4) -0.004(5) C10 0.082(4) 0.070(5) 0.127(5) -0.007(3) 0.016(4) 0.000(4) C11 0.086(5) 0.070(5) 0.103(5) 0.006(4) 0.003(4) 0.004(4) C12 0.068(4) 0.080(5) 0.131(5) -0.003(4) 0.011(3) 0.010(4) C13 0.092(5) 0.102(6) 0.096(5) 0.010(5) 0.010(4) 0.007(4) #============================================================================== _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku, 2000-2010)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure (Rigaku, 2000-2010)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C13 1.339(8) yes . . F2 C13 1.330(8) yes . . F3 C13 1.350(8) yes . . O1 C11 1.210(8) yes . . O2 C11 1.326(8) yes . . O2 C12 1.452(6) yes . . N1 C1 1.275(9) yes . . N1 C2 1.458(8) yes . . C1 C4 1.511(9) yes . . C1 C5 1.492(10) yes . . C2 C3 1.569(8) yes . . C2 C11 1.527(8) yes . . C3 C4 1.521(9) yes . . C3 C13 1.473(9) yes . . C5 C6 1.404(9) yes . . C5 C10 1.417(9) yes . . C6 C7 1.379(10) yes . . C7 C8 1.375(10) yes . . C8 C9 1.410(10) yes . . C9 C10 1.394(10) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C11 O2 C12 114.3(4) yes . . . C1 N1 C2 108.8(5) yes . . . N1 C1 C4 117.3(6) yes . . . N1 C1 C5 120.5(6) yes . . . C4 C1 C5 122.2(6) yes . . . N1 C2 C3 107.2(5) yes . . . N1 C2 C11 107.0(5) yes . . . C3 C2 C11 113.2(5) yes . . . C2 C3 C4 104.4(5) yes . . . C2 C3 C13 111.7(5) yes . . . C4 C3 C13 113.8(5) yes . . . C1 C4 C3 101.8(5) yes . . . C1 C5 C6 121.7(6) yes . . . C1 C5 C10 120.6(6) yes . . . C6 C5 C10 117.6(6) yes . . . C5 C6 C7 121.1(6) yes . . . C6 C7 C8 121.4(6) yes . . . C7 C8 C9 119.3(6) yes . . . C8 C9 C10 119.6(6) yes . . . C5 C10 C9 121.0(6) yes . . . O1 C11 O2 125.4(6) yes . . . O1 C11 C2 123.0(6) yes . . . O2 C11 C2 111.6(5) yes . . . F1 C13 F2 106.8(5) yes . . . F1 C13 F3 106.4(5) yes . . . F1 C13 C3 111.9(6) yes . . . F2 C13 F3 105.6(5) yes . . . F2 C13 C3 113.6(6) yes . . . F3 C13 C3 112.0(6) yes . . . #===END