# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_General _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- 2CIF.cif' _audit_creation_date 2012-02-08 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name 'Norio Shibata' _publ_contact_author_email nozshiba@nitech.ac.jp _publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_footnote _publ_author_address ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #============================================================================== # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Johnson, C.K. (1976). ORTEP-II. A FORTRAN Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Rigaku (1998). PROCESS-AUTO. Automatic Data Acquisition and Processing Package for Imaging Plate Diffractometer. Rigaku Corporation, Tokyo 196-8666, Japan Rigaku (2000-2010). CrystalStructure 4.0.1: Crystal Structure Analysis Package. Rigaku Corporation, Tokyo 196-8666, Japan. Sheldrick, G.M. (1997). SHELXS97. Program for the Solution of Crystal Structures. University of Gottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; loop_ _publ_author_name 'Hiroyuki Kawai' 'Takashi Kitayama' 'Etsuko Tokunaga' 'Takashi Matsumoto' 'Hiroyasu Sato' data_KH-2474 _database_code_depnum_ccdc_archive 'CCDC 859930' #TrackingRef '- CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C11 H9 Br F3 N' _chemical_formula_moiety 'C11 H9 Br F3 N' _chemical_formula_weight 292.10 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 13.2977(11) _cell_length_b 5.6489(4) _cell_length_c 16.1262(12) _cell_angle_alpha 90.0000 _cell_angle_beta 115.166(8) _cell_angle_gamma 90.0000 _cell_volume 1096.38(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8347 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.47 _cell_measurement_temperature 173 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.116 _exptl_crystal_size_min 0.055 _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576.00 _exptl_absorpt_coefficient_mu 3.771 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.458 _exptl_absorpt_correction_T_max 0.813 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 173 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 9916 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _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 2493 _reflns_number_gt 2030 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1107 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2493 _refine_ls_number_parameters 145 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0647P)^2^+2.4100P] 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 0.001 _refine_diff_density_max 0.840 _refine_diff_density_min -0.420 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 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) ; Br Br -0.2901 2.4595 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0061 0.0033 ; 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 Br1 Br 0.22378(3) 0.04546(8) 0.65464(2) 0.04165(15) Uani 1.0 4 d . . . F1 F 0.9577(3) -0.1819(7) 1.0542(2) 0.0739(9) Uani 1.0 4 d . . . F2 F 0.9878(2) 0.1650(6) 1.1158(2) 0.0701(8) Uani 1.0 4 d . . . F3 F 1.02752(19) -0.1482(6) 1.20133(18) 0.0659(8) Uani 1.0 4 d . . . N1 N 0.6791(3) -0.3102(5) 1.04690(19) 0.0319(6) Uani 1.0 4 d . . . C1 C 0.6583(3) -0.1214(6) 0.9985(2) 0.0261(7) Uani 1.0 4 d . . . C2 C 0.4383(3) 0.1688(6) 0.7902(3) 0.0293(7) Uani 1.0 4 d . . . C5 C 0.8384(3) -0.0479(7) 1.1186(3) 0.0381(8) Uani 1.0 4 d . . . C6 C 0.5357(3) 0.1293(6) 0.8679(3) 0.0293(7) Uani 1.0 4 d . . . C7 C 0.3690(3) -0.2091(6) 0.8132(3) 0.0288(7) Uani 1.0 4 d . . . C8 C 0.7520(3) 0.0573(7) 1.0286(3) 0.0372(8) Uani 1.0 4 d . . . C9 C 0.4669(3) -0.2477(6) 0.8908(2) 0.0271(7) Uani 1.0 4 d . . . C10 C 0.7926(3) -0.3010(7) 1.1201(3) 0.0383(8) Uani 1.0 4 d . . . C11 C 0.9516(4) -0.0513(9) 1.1233(3) 0.0490(10) Uani 1.0 4 d . . . C12 C 0.3564(3) -0.0045(6) 0.7630(3) 0.0279(7) Uani 1.0 4 d . . . C13 C 0.5527(3) -0.0792(6) 0.9189(2) 0.0238(6) Uani 1.0 4 d . . . H2A H 0.4279 0.3083 0.7569 0.0351 Uiso 1.0 4 calc R . . H5 H 0.8385 0.0437 1.1703 0.0457 Uiso 1.0 4 calc R . . H6A H 0.5910 0.2442 0.8867 0.0351 Uiso 1.0 4 calc R . . H7A H 0.3122 -0.3206 0.7951 0.0346 Uiso 1.0 4 calc R . . H8A H 0.7271 0.2116 1.0386 0.0446 Uiso 1.0 4 calc R . . H8B H 0.7819 0.0718 0.9835 0.0446 Uiso 1.0 4 calc R . . H9A H 0.4758 -0.3860 0.9245 0.0325 Uiso 1.0 4 calc R . . H10A H 0.8389 -0.4191 1.1097 0.0459 Uiso 1.0 4 calc R . . H10B H 0.7919 -0.3318 1.1791 0.0459 Uiso 1.0 4 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 Br1 0.0315(2) 0.0529(3) 0.0349(3) 0.00803(15) 0.00867(15) 0.00411(16) F1 0.0607(17) 0.105(3) 0.0668(18) 0.0079(17) 0.0375(15) -0.0125(17) F2 0.0482(15) 0.080(2) 0.082(2) -0.0302(14) 0.0284(14) -0.0068(16) F3 0.0329(12) 0.091(3) 0.0566(16) 0.0049(13) 0.0028(11) 0.0024(15) N1 0.0326(15) 0.0277(16) 0.0318(15) -0.0034(11) 0.0102(12) 0.0007(11) C1 0.0307(16) 0.0208(15) 0.0302(16) -0.0049(12) 0.0161(13) -0.0025(12) C2 0.0379(17) 0.0206(17) 0.0329(17) 0.0010(13) 0.0184(14) 0.0042(12) C5 0.0365(19) 0.039(2) 0.0359(19) -0.0039(15) 0.0129(16) -0.0029(15) C6 0.0319(16) 0.0239(17) 0.0346(17) -0.0015(13) 0.0165(14) -0.0007(13) C7 0.0274(16) 0.0295(18) 0.0315(17) -0.0046(12) 0.0144(14) -0.0032(13) C8 0.0332(18) 0.032(2) 0.0406(19) -0.0090(14) 0.0103(15) 0.0018(15) C9 0.0343(17) 0.0197(16) 0.0305(16) -0.0028(12) 0.0169(14) 0.0008(12) C10 0.0316(18) 0.034(2) 0.0396(19) -0.0033(14) 0.0058(15) 0.0020(14) C11 0.038(2) 0.058(3) 0.047(3) -0.0073(19) 0.0146(18) -0.0028(19) C12 0.0296(16) 0.0302(19) 0.0248(15) 0.0065(12) 0.0126(13) 0.0001(12) C13 0.0283(15) 0.0208(17) 0.0266(15) -0.0026(11) 0.0161(13) -0.0015(11) #============================================================================== _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 Br1 C12 1.903(3) yes . . F1 C11 1.367(7) yes . . F2 C11 1.337(6) yes . . F3 C11 1.350(5) yes . . N1 C1 1.280(5) yes . . N1 C10 1.469(4) yes . . C1 C8 1.514(5) yes . . C1 C13 1.464(4) yes . . C2 C6 1.385(4) yes . . C2 C12 1.389(5) yes . . C5 C8 1.536(5) yes . . C5 C10 1.559(6) yes . . C5 C11 1.476(7) yes . . C6 C13 1.398(5) yes . . C7 C9 1.387(4) yes . . C7 C12 1.380(5) yes . . C9 C13 1.405(5) 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 C1 N1 C10 110.0(3) yes . . . N1 C1 C8 115.2(3) yes . . . N1 C1 C13 123.2(3) yes . . . C8 C1 C13 121.6(3) yes . . . C6 C2 C12 118.5(3) yes . . . C8 C5 C10 103.3(3) yes . . . C8 C5 C11 113.0(4) yes . . . C10 C5 C11 112.6(4) yes . . . C2 C6 C13 121.6(3) yes . . . C9 C7 C12 119.6(3) yes . . . C1 C8 C5 103.1(3) yes . . . C7 C9 C13 120.4(3) yes . . . N1 C10 C5 107.1(3) yes . . . F1 C11 F2 105.7(5) yes . . . F1 C11 F3 105.1(4) yes . . . F1 C11 C5 112.2(4) yes . . . F2 C11 F3 107.4(3) yes . . . F2 C11 C5 112.5(4) yes . . . F3 C11 C5 113.3(5) yes . . . Br1 C12 C2 118.8(3) yes . . . Br1 C12 C7 119.8(3) yes . . . C2 C12 C7 121.4(3) yes . . . C1 C13 C6 120.5(3) yes . . . C1 C13 C9 121.1(3) yes . . . C6 C13 C9 118.3(3) yes . . . #===END======================================================================== #============================================================================== data_KT-414 _database_code_depnum_ccdc_archive 'CCDC 866120' #TrackingRef '- 2CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H12 F3 N O3' _chemical_formula_moiety 'C15 H12 F3 N O3' _chemical_formula_weight 311.26 _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 5.25232(10) _cell_length_b 20.3901(4) _cell_length_c 12.9093(3) _cell_angle_alpha 90.0000 _cell_angle_beta 94.170(7) _cell_angle_gamma 90.0000 _cell_volume 1378.87(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 23524 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 68.19 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.323 _exptl_crystal_size_mid 0.233 _exptl_crystal_size_min 0.132 _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640.00 _exptl_absorpt_coefficient_mu 1.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.708 _exptl_absorpt_correction_T_max 0.860 #============================================================================== # 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 26449 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_theta_max 68.19 _diffrn_reflns_theta_full 68.19 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _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 5028 _reflns_number_gt 5004 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0647 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5028 _refine_ls_number_parameters 397 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.1543P] 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 0.001 _refine_diff_density_max 0.190 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2419 Friedel Pairs' _refine_ls_abs_structure_Flack 0.01(6) 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 0.05541(19) 0.69353(5) 0.35019(7) 0.0408(2) Uani 1.0 2 d . . . F2 F 0.40037(15) 0.69636(4) 0.27041(7) 0.0353(2) Uani 1.0 2 d . . . F3 F 0.08293(17) 0.75652(4) 0.21755(7) 0.0370(2) Uani 1.0 2 d . . . O1 O -0.19392(18) 0.58632(5) 0.00912(8) 0.0306(3) Uani 1.0 2 d . . . O2 O -0.31812(17) 0.58246(5) 0.30546(8) 0.0310(3) Uani 1.0 2 d . . . O3 O -0.0137(2) 0.53278(5) 0.39495(8) 0.0356(3) Uani 1.0 2 d . . . N1 N -0.0979(2) 0.56314(5) 0.31871(9) 0.0237(3) Uani 1.0 2 d . . . C1 C 0.1255(3) 0.60402(6) -0.10762(10) 0.0234(3) Uani 1.0 2 d . . . C2 C 0.0164(3) 0.55832(7) -0.18128(11) 0.0272(3) Uani 1.0 2 d . . . H2 H -0.1201 0.5310 -0.1634 0.0327 Uiso 1.0 2 calc R . . C3 C 0.1068(3) 0.55358(7) -0.27754(11) 0.0290(3) Uani 1.0 2 d . . . H3 H 0.0358 0.5218 -0.3251 0.0348 Uiso 1.0 2 calc R . . C4 C 0.3045(3) 0.59521(7) -0.30778(10) 0.0267(3) Uani 1.0 2 d . . . C5 C 0.3917(3) 0.59391(8) -0.40889(11) 0.0333(4) Uani 1.0 2 d . . . H5 H 0.3171 0.5642 -0.4590 0.0399 Uiso 1.0 2 calc R . . C6 C 0.5824(4) 0.63504(8) -0.43539(12) 0.0376(4) Uani 1.0 2 d . . . H6 H 0.6384 0.6338 -0.5037 0.0451 Uiso 1.0 2 calc R . . C7 C 0.6963(3) 0.67926(7) -0.36212(12) 0.0339(4) Uani 1.0 2 d . . . H7 H 0.8289 0.7075 -0.3813 0.0407 Uiso 1.0 2 calc R . . C8 C 0.6172(3) 0.68184(7) -0.26349(11) 0.0282(3) Uani 1.0 2 d . . . H8 H 0.6964 0.7116 -0.2145 0.0338 Uiso 1.0 2 calc R . . C9 C 0.4177(3) 0.64041(6) -0.23370(10) 0.0241(3) Uani 1.0 2 d . . . C10 C 0.3253(3) 0.64295(6) -0.13380(10) 0.0233(3) Uani 1.0 2 d . . . H10 H 0.4026 0.6722 -0.0835 0.0280 Uiso 1.0 2 calc R . . C11 C 0.0146(3) 0.60965(7) -0.00554(11) 0.0243(3) Uani 1.0 2 d . . . C12 C 0.1679(3) 0.64590(7) 0.08161(11) 0.0259(3) Uani 1.0 2 d . . . H12A H 0.1875 0.6924 0.0613 0.0311 Uiso 1.0 2 calc R . . H12B H 0.3405 0.6264 0.0913 0.0311 Uiso 1.0 2 calc R . . C13 C 0.0403(3) 0.64290(6) 0.18480(10) 0.0241(3) Uani 1.0 2 d . . . H13 H -0.1470 0.6505 0.1700 0.0290 Uiso 1.0 2 calc R . . C14 C 0.1453(3) 0.69678(7) 0.25640(11) 0.0278(3) Uani 1.0 2 d . . . C15 C 0.0775(3) 0.57511(6) 0.23420(10) 0.0238(3) Uani 1.0 2 d . . . H15A H 0.0472 0.5412 0.1798 0.0286 Uiso 1.0 2 calc R . . H15B H 0.2564 0.5708 0.2633 0.0286 Uiso 1.0 2 calc R . . F4 F 0.41560(16) 0.26336(4) 0.95021(6) 0.02956(18) Uani 1.0 2 d . . . F5 F 0.10716(14) 0.32716(4) 0.98457(6) 0.02731(16) Uani 1.0 2 d . . . F6 F 0.45793(16) 0.32873(4) 1.08138(6) 0.03115(18) Uani 1.0 2 d . . . O4 O 0.71194(17) 0.42589(5) 0.75038(7) 0.0263(2) Uani 1.0 2 d . . . O5 O 0.5037(2) 0.48769(5) 1.12364(8) 0.0347(3) Uani 1.0 2 d . . . O6 O 0.82291(17) 0.44503(5) 1.05119(7) 0.0279(2) Uani 1.0 2 d . . . N2 N 0.5981(2) 0.45971(5) 1.05181(8) 0.0230(3) Uani 1.0 2 d . . . C16 C 0.4108(3) 0.39751(6) 0.61245(10) 0.0207(3) Uani 1.0 2 d . . . C17 C 0.5427(3) 0.43350(7) 0.53858(10) 0.0235(3) Uani 1.0 2 d . . . H17 H 0.6862 0.4595 0.5610 0.0283 Uiso 1.0 2 calc R . . C18 C 0.4638(3) 0.43076(7) 0.43569(10) 0.0261(3) Uani 1.0 2 d . . . H18 H 0.5515 0.4557 0.3873 0.0313 Uiso 1.0 2 calc R . . C19 C 0.2534(3) 0.39136(6) 0.39977(10) 0.0231(3) Uani 1.0 2 d . . . C20 C 0.1711(3) 0.38672(7) 0.29294(10) 0.0300(3) Uani 1.0 2 d . . . H20 H 0.2582 0.4106 0.2432 0.0360 Uiso 1.0 2 calc R . . C21 C -0.0328(3) 0.34807(7) 0.26101(10) 0.0319(3) Uani 1.0 2 d . . . H21 H -0.0851 0.3451 0.1892 0.0382 Uiso 1.0 2 calc R . . C22 C -0.1655(3) 0.31274(7) 0.33324(11) 0.0306(3) Uani 1.0 2 d . . . H22 H -0.3073 0.2863 0.3100 0.0367 Uiso 1.0 2 calc R . . C23 C -0.0916(3) 0.31613(7) 0.43707(10) 0.0270(3) Uani 1.0 2 d . . . H23 H -0.1826 0.2920 0.4854 0.0324 Uiso 1.0 2 calc R . . C24 C 0.1201(3) 0.35540(6) 0.47309(10) 0.0215(3) Uani 1.0 2 d . . . C25 C 0.2033(3) 0.35989(6) 0.57946(9) 0.0216(3) Uani 1.0 2 d . . . H25 H 0.1140 0.3365 0.6291 0.0259 Uiso 1.0 2 calc R . . C26 C 0.5078(3) 0.40049(6) 0.72329(10) 0.0206(3) Uani 1.0 2 d . . . C27 C 0.3456(3) 0.36945(6) 0.80320(9) 0.0214(3) Uani 1.0 2 d . . . H27A H 0.3204 0.3224 0.7865 0.0256 Uiso 1.0 2 calc R . . H27B H 0.1756 0.3907 0.7990 0.0256 Uiso 1.0 2 calc R . . C28 C 0.4683(3) 0.37605(6) 0.91421(9) 0.0202(3) Uani 1.0 2 d . . . H28 H 0.6562 0.3688 0.9126 0.0242 Uiso 1.0 2 calc R . . C29 C 0.3614(3) 0.32413(6) 0.98271(10) 0.0221(3) Uani 1.0 2 d . . . C30 C 0.4252(3) 0.44472(6) 0.95641(10) 0.0216(3) Uani 1.0 2 d . . . H30A H 0.4552 0.4774 0.9018 0.0259 Uiso 1.0 2 calc R . . H30B H 0.2453 0.4489 0.9736 0.0259 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 0.0539(6) 0.0344(5) 0.0350(5) -0.0055(4) 0.0083(4) -0.0111(4) F2 0.0279(5) 0.0278(5) 0.0487(5) 0.0010(4) -0.0084(4) -0.0092(4) F3 0.0415(5) 0.0214(5) 0.0472(5) 0.0088(4) -0.0038(4) -0.0040(4) F4 0.0377(5) 0.0188(4) 0.0321(4) 0.0059(4) 0.0018(4) 0.0000(3) F5 0.0228(4) 0.0279(4) 0.0316(4) -0.0007(3) 0.0044(3) 0.0033(4) F6 0.0402(5) 0.0324(5) 0.0199(4) -0.0042(4) -0.0048(3) 0.0033(3) O1 0.0240(5) 0.0338(6) 0.0332(5) -0.0073(4) -0.0032(4) 0.0043(4) O2 0.0186(5) 0.0392(6) 0.0350(5) 0.0037(4) 0.0011(4) -0.0037(5) O3 0.0346(6) 0.0385(6) 0.0332(6) 0.0054(5) -0.0009(4) 0.0080(5) O4 0.0234(5) 0.0302(5) 0.0250(5) -0.0065(4) -0.0004(4) -0.0024(4) O5 0.0411(6) 0.0350(6) 0.0295(5) -0.0082(5) 0.0140(5) -0.0124(5) O6 0.0235(5) 0.0298(5) 0.0296(5) 0.0013(4) -0.0026(4) -0.0032(4) N1 0.0207(5) 0.0217(6) 0.0283(6) -0.0008(5) -0.0012(4) -0.0053(5) N2 0.0273(6) 0.0196(5) 0.0227(6) -0.0034(5) 0.0050(5) -0.0009(4) C1 0.0222(6) 0.0179(6) 0.0291(7) 0.0018(5) -0.0061(5) 0.0020(5) C2 0.0263(7) 0.0189(6) 0.0351(7) -0.0006(6) -0.0065(6) 0.0008(6) C3 0.0309(7) 0.0209(7) 0.0334(7) 0.0008(6) -0.0099(6) -0.0051(6) C4 0.0280(7) 0.0225(7) 0.0283(7) 0.0078(5) -0.0061(6) -0.0014(6) C5 0.0379(8) 0.0298(8) 0.0311(7) 0.0093(6) -0.0046(6) -0.0053(6) C6 0.0463(9) 0.0371(8) 0.0300(8) 0.0115(7) 0.0075(7) 0.0001(7) C7 0.0348(8) 0.0286(8) 0.0392(8) 0.0042(6) 0.0084(6) 0.0038(6) C8 0.0305(7) 0.0202(7) 0.0336(7) 0.0020(6) 0.0010(6) -0.0017(5) C9 0.0243(6) 0.0176(6) 0.0295(7) 0.0054(5) -0.0028(5) 0.0003(5) C10 0.0236(6) 0.0184(6) 0.0271(6) 0.0011(5) -0.0039(5) -0.0016(5) C11 0.0222(6) 0.0185(6) 0.0314(7) 0.0002(6) -0.0043(5) 0.0040(5) C12 0.0209(6) 0.0246(7) 0.0323(7) -0.0026(6) 0.0018(5) -0.0036(6) C13 0.0194(6) 0.0226(7) 0.0301(7) 0.0012(5) -0.0005(5) -0.0025(6) C14 0.0270(7) 0.0232(7) 0.0326(7) 0.0053(6) -0.0007(6) -0.0019(6) C15 0.0186(6) 0.0222(7) 0.0306(7) 0.0019(5) 0.0009(5) -0.0043(5) C16 0.0212(6) 0.0191(6) 0.0218(6) 0.0017(5) 0.0016(5) -0.0011(5) C17 0.0223(6) 0.0210(6) 0.0273(7) -0.0025(5) 0.0017(5) -0.0022(5) C18 0.0300(7) 0.0249(7) 0.0238(6) -0.0017(6) 0.0046(5) 0.0034(5) C19 0.0264(7) 0.0204(6) 0.0224(6) 0.0035(5) 0.0009(5) -0.0006(5) C20 0.0368(8) 0.0305(8) 0.0227(7) 0.0021(6) 0.0014(6) 0.0007(6) C21 0.0383(8) 0.0339(8) 0.0222(6) 0.0065(6) -0.0059(6) -0.0038(6) C22 0.0290(7) 0.0292(7) 0.0322(7) -0.0004(6) -0.0077(6) -0.0079(6) C23 0.0261(7) 0.0263(7) 0.0279(7) -0.0018(6) -0.0019(5) -0.0012(6) C24 0.0222(6) 0.0187(6) 0.0234(6) 0.0036(5) 0.0008(5) -0.0023(5) C25 0.0221(6) 0.0218(6) 0.0211(6) -0.0025(5) 0.0031(5) 0.0008(5) C26 0.0208(6) 0.0180(6) 0.0229(6) 0.0015(5) 0.0008(5) -0.0029(5) C27 0.0187(6) 0.0246(7) 0.0205(6) -0.0021(5) -0.0013(5) -0.0005(5) C28 0.0182(6) 0.0215(6) 0.0207(6) 0.0036(5) 0.0000(5) -0.0008(5) C29 0.0232(6) 0.0204(7) 0.0225(6) 0.0025(5) -0.0009(5) -0.0010(5) C30 0.0198(6) 0.0204(7) 0.0244(6) 0.0020(5) 0.0002(5) 0.0001(5) #============================================================================== _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 C14 1.3328(18) yes . . F2 C14 1.3387(16) yes . . F3 C14 1.3486(17) yes . . F4 C29 1.3453(15) yes . . F5 C29 1.3389(15) yes . . F6 C29 1.3395(15) yes . . O1 C11 1.2212(17) yes . . O2 N1 1.2219(14) yes . . O3 N1 1.2183(15) yes . . O4 C26 1.2190(15) yes . . O5 N2 1.2239(15) yes . . O6 N2 1.2187(14) yes . . N1 C15 1.4983(18) yes . . N2 C30 1.5075(16) yes . . C1 C2 1.4219(19) yes . . C1 C10 1.3774(18) yes . . C1 C11 1.484(2) yes . . C2 C3 1.366(2) yes . . C3 C4 1.418(2) yes . . C4 C5 1.415(2) yes . . C4 C9 1.4265(19) yes . . C5 C6 1.369(3) yes . . C6 C7 1.408(3) yes . . C7 C8 1.369(3) yes . . C8 C9 1.4207(19) yes . . C9 C10 1.4116(19) yes . . C11 C12 1.5261(19) yes . . C12 C13 1.535(2) yes . . C13 C14 1.5138(19) yes . . C13 C15 1.5288(18) yes . . C16 C17 1.4224(19) yes . . C16 C25 1.3752(18) yes . . C16 C26 1.4847(18) yes . . C17 C18 1.3633(18) yes . . C18 C19 1.4169(19) yes . . C19 C20 1.4181(18) yes . . C19 C24 1.4214(19) yes . . C20 C21 1.369(2) yes . . C21 C22 1.403(2) yes . . C22 C23 1.3698(19) yes . . C23 C24 1.4206(19) yes . . C24 C25 1.4134(17) yes . . C26 C27 1.5227(18) yes . . C27 C28 1.5340(17) yes . . C28 C29 1.5132(18) yes . . C28 C30 1.5253(18) 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 O2 N1 O3 124.14(12) yes . . . O2 N1 C15 118.13(11) yes . . . O3 N1 C15 117.69(11) yes . . . O5 N2 O6 124.43(11) yes . . . O5 N2 C30 117.40(11) yes . . . O6 N2 C30 118.12(10) yes . . . C2 C1 C10 119.40(13) yes . . . C2 C1 C11 118.66(12) yes . . . C10 C1 C11 121.92(12) yes . . . C1 C2 C3 120.34(13) yes . . . C2 C3 C4 121.22(13) yes . . . C3 C4 C5 122.39(13) yes . . . C3 C4 C9 118.70(12) yes . . . C5 C4 C9 118.91(13) yes . . . C4 C5 C6 120.74(14) yes . . . C5 C6 C7 120.48(15) yes . . . C6 C7 C8 120.44(15) yes . . . C7 C8 C9 120.58(13) yes . . . C4 C9 C8 118.85(13) yes . . . C4 C9 C10 118.81(12) yes . . . C8 C9 C10 122.34(12) yes . . . C1 C10 C9 121.45(12) yes . . . O1 C11 C1 121.47(13) yes . . . O1 C11 C12 120.36(13) yes . . . C1 C11 C12 118.17(11) yes . . . C11 C12 C13 112.34(11) yes . . . C12 C13 C14 109.76(11) yes . . . C12 C13 C15 110.32(11) yes . . . C14 C13 C15 111.81(11) yes . . . F1 C14 F2 107.10(11) yes . . . F1 C14 F3 106.87(12) yes . . . F1 C14 C13 112.40(12) yes . . . F2 C14 F3 105.65(11) yes . . . F2 C14 C13 113.24(12) yes . . . F3 C14 C13 111.13(11) yes . . . N1 C15 C13 112.60(11) yes . . . C17 C16 C25 119.59(12) yes . . . C17 C16 C26 118.39(11) yes . . . C25 C16 C26 122.00(12) yes . . . C16 C17 C18 120.26(12) yes . . . C17 C18 C19 121.09(13) yes . . . C18 C19 C20 122.10(13) yes . . . C18 C19 C24 119.01(12) yes . . . C20 C19 C24 118.89(12) yes . . . C19 C20 C21 120.51(13) yes . . . C20 C21 C22 120.73(13) yes . . . C21 C22 C23 120.36(13) yes . . . C22 C23 C24 120.53(13) yes . . . C19 C24 C23 118.98(12) yes . . . C19 C24 C25 118.75(12) yes . . . C23 C24 C25 122.26(12) yes . . . C16 C25 C24 121.28(12) yes . . . O4 C26 C16 121.78(12) yes . . . O4 C26 C27 120.41(12) yes . . . C16 C26 C27 117.80(11) yes . . . C26 C27 C28 112.25(10) yes . . . C27 C28 C29 109.63(10) yes . . . C27 C28 C30 110.55(10) yes . . . C29 C28 C30 111.25(11) yes . . . F4 C29 F5 106.38(10) yes . . . F4 C29 F6 106.68(10) yes . . . F4 C29 C28 111.49(11) yes . . . F5 C29 F6 106.78(11) yes . . . F5 C29 C28 113.02(10) yes . . . F6 C29 C28 112.08(10) yes . . . N2 C30 C28 112.43(10) yes . . . #===END========================================================================