# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_c:\users\zhoupan\desktop\zp-65\355k\355k _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C0.88 H2 F0.38 N0.13 O0.38 S0.13' _chemical_formula_weight 31.41 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P4/nmm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x, z' '-x+1/2, -y+1/2, z' 'y, -x+1/2, z' 'x+1/2, -y, -z' '-x, y+1/2, -z' 'y+1/2, x+1/2, -z' '-y, -x, -z' '-x, -y, -z' 'y-1/2, -x, -z' 'x-1/2, y-1/2, -z' '-y, x-1/2, -z' '-x-1/2, y, z' 'x, -y-1/2, z' '-y-1/2, -x-1/2, z' 'y, x, z' _cell_length_a 8.9683(8) _cell_length_b 8.9683(8) _cell_length_c 8.2107(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 660.39(12) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2100 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 26.37 _reflns_number_total 414 _reflns_number_gt 228 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1209P)^2^+0.0875P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 414 _refine_ls_number_parameters 39 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.2548 _refine_ls_wR_factor_gt 0.2154 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _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 S1 S 0.2500 0.2500 0.3438(3) 0.1521(17) Uani 1 8 d S . . C1 C 0.2500 0.2500 0.1343(17) 0.176(4) Uani 1 8 d S . . F4 F 0.1546(5) 0.3454(5) 0.0732(8) 0.284(4) Uani 0.75 2 d SP . . O5 O 0.1744(11) 0.3848(14) 0.3826(11) 0.212(7) Uani 0.38 1 d P . . C2 C 0.2500 0.6105(9) 0.7441(9) 0.206(3) Uani 1 2 d S . . H2A H 0.1766 0.6186 0.8321 0.309 Uiso 0.50 1 calc PR . . H2C H 0.3493 0.5945 0.7907 0.309 Uiso 0.50 1 calc PR . . H2B H 0.2241 0.5262 0.6736 0.309 Uiso 0.50 1 calc PR . . N1 N 0.1888(8) 0.6888(8) 0.5000 0.113(4) Uani 0.25 2 d SP . . C3 C 0.2500 0.7500 0.6470(11) 0.262(7) Uani 1 4 d S . . H1B H 0.1544 0.7500 0.6117 0.32(18) Uiso 0.50 2 d SPR . . H1A H 0.1191 0.6994 0.4960 0.387 Uiso 0.25 1 d PR . . 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 S1 0.159(2) 0.159(2) 0.139(2) 0.000 0.000 0.000 C1 0.188(7) 0.188(7) 0.153(10) 0.000 0.000 0.000 F4 0.323(5) 0.323(5) 0.207(5) 0.069(3) -0.069(3) 0.054(4) O5 0.246(19) 0.160(6) 0.231(6) -0.049(5) 0.059(5) 0.003(9) C2 0.194(6) 0.275(9) 0.149(5) -0.019(5) 0.000 0.000 N1 0.101(5) 0.101(5) 0.139(10) 0.017(5) -0.017(5) -0.001(4) C3 0.28(2) 0.41(3) 0.087(5) 0.000 0.000 0.000 _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 S1 O5 1.422(9) 4 ? S1 O5 1.422(9) 16 ? S1 O5 1.422(9) 13_655 ? S1 O5 1.422(9) 3 ? S1 O5 1.422(9) 14_565 ? S1 O5 1.422(9) . ? S1 O5 1.422(9) 2 ? S1 O5 1.422(9) 15_665 ? S1 C1 1.721(14) . ? C1 F4 1.309(6) 2 ? C1 F4 1.309(6) . ? C1 F4 1.309(6) 4 ? C1 F4 1.309(6) 3 ? F4 F4 1.711(9) 2 ? F4 F4 1.711(9) 4 ? O5 O5 0.75(3) 15_665 ? O5 O5 1.36(2) 13_655 ? C2 C3 1.484(8) . ? N1 N1 1.097(14) 12_666 ? N1 N1 1.097(14) 10_566 ? N1 C3 1.435(9) 10_566 ? N1 C3 1.435(9) . ? N1 N1 1.551(19) 3_565 ? C3 N1 1.435(9) 10_566 ? C3 N1 1.435(9) 12_666 ? C3 N1 1.435(9) 3_565 ? C3 C2 1.484(8) 3_565 ? 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 O5 S1 O5 57.0(11) 4 16 ? O5 S1 O5 30.6(11) 4 13_655 ? O5 S1 O5 87.13(17) 16 13_655 ? O5 S1 O5 87.13(17) 4 3 ? O5 S1 O5 30.6(11) 16 3 ? O5 S1 O5 116.4(11) 13_655 3 ? O5 S1 O5 139.5(9) 4 14_565 ? O5 S1 O5 87.13(17) 16 14_565 ? O5 S1 O5 154.2(8) 13_655 14_565 ? O5 S1 O5 57.0(11) 3 14_565 ? O5 S1 O5 87.13(17) 4 . ? O5 S1 O5 139.5(9) 16 . ? O5 S1 O5 57.0(11) 13_655 . ? O5 S1 O5 154.2(8) 3 . ? O5 S1 O5 116.4(11) 14_565 . ? O5 S1 O5 154.2(8) 4 2 ? O5 S1 O5 116.4(11) 16 2 ? O5 S1 O5 139.5(9) 13_655 2 ? O5 S1 O5 87.13(17) 3 2 ? O5 S1 O5 30.6(11) 14_565 2 ? O5 S1 O5 87.13(17) . 2 ? O5 S1 O5 116.4(11) 4 15_665 ? O5 S1 O5 154.2(8) 16 15_665 ? O5 S1 O5 87.13(17) 13_655 15_665 ? O5 S1 O5 139.5(9) 3 15_665 ? O5 S1 O5 87.13(17) 14_565 15_665 ? O5 S1 O5 30.6(11) . 15_665 ? O5 S1 O5 57.0(11) 2 15_665 ? O5 S1 C1 102.9(4) 4 . ? O5 S1 C1 102.9(4) 16 . ? O5 S1 C1 102.9(4) 13_655 . ? O5 S1 C1 102.9(4) 3 . ? O5 S1 C1 102.9(4) 14_565 . ? O5 S1 C1 102.9(4) . . ? O5 S1 C1 102.9(4) 2 . ? O5 S1 C1 102.9(4) 15_665 . ? F4 C1 F4 81.6(4) 2 . ? F4 C1 F4 135.0(12) 2 4 ? F4 C1 F4 81.6(4) . 4 ? F4 C1 F4 81.6(4) 2 3 ? F4 C1 F4 135.0(12) . 3 ? F4 C1 F4 81.6(4) 4 3 ? F4 C1 S1 112.5(6) 2 . ? F4 C1 S1 112.5(6) . . ? F4 C1 S1 112.5(6) 4 . ? F4 C1 S1 112.5(6) 3 . ? C1 F4 F4 49.2(2) . 2 ? C1 F4 F4 49.2(2) . 4 ? F4 F4 F4 89.999(1) 2 4 ? O5 O5 O5 135.000(6) 15_665 13_655 ? O5 O5 S1 74.7(5) 15_665 . ? O5 O5 S1 61.5(5) 13_655 . ? N1 N1 N1 90.0 12_666 10_566 ? N1 N1 C3 67.5(3) 12_666 10_566 ? N1 N1 C3 67.5(3) 10_566 10_566 ? N1 N1 C3 67.5(3) 12_666 . ? N1 N1 C3 67.5(3) 10_566 . ? C3 N1 C3 114.6(8) 10_566 . ? N1 N1 N1 45.0 12_666 3_565 ? N1 N1 N1 44.998(3) 10_566 3_565 ? C3 N1 N1 57.3(4) 10_566 3_565 ? C3 N1 N1 57.3(4) . 3_565 ? N1 C3 N1 44.9(5) . 10_566 ? N1 C3 N1 44.9(5) . 12_666 ? N1 C3 N1 65.4(8) 10_566 12_666 ? N1 C3 N1 65.4(8) . 3_565 ? N1 C3 N1 44.9(5) 10_566 3_565 ? N1 C3 N1 44.9(5) 12_666 3_565 ? N1 C3 C2 97.5(4) . . ? N1 C3 C2 140.8(4) 10_566 . ? N1 C3 C2 97.5(4) 12_666 . ? N1 C3 C2 140.8(4) 3_565 . ? N1 C3 C2 140.8(4) . 3_565 ? N1 C3 C2 97.5(4) 10_566 3_565 ? N1 C3 C2 140.8(4) 12_666 3_565 ? N1 C3 C2 97.5(4) 3_565 3_565 ? C2 C3 C2 115.0(7) . 3_565 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.191 _refine_diff_density_min -0.099 _refine_diff_density_rms 0.026 _database_code_depnum_ccdc_archive 'CCDC 971791' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3.50 H8 F1.50 N0.50 O1.50 S0.50' _chemical_formula_weight 125.64 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 12.483(8) _cell_length_b 12.806(8) _cell_length_c 8.094(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.388(8) _cell_angle_gamma 90.00 _cell_volume 1290.2(14) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4784 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.05 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1505 _reflns_number_gt 1151 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.2000P)^2^+0.0000P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1505 _refine_ls_number_parameters 95 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.3371 _refine_ls_wR_factor_gt 0.3180 _refine_ls_goodness_of_fit_ref 1.357 _refine_ls_restrained_S_all 1.398 _refine_ls_shift/su_max 0.000 _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 S1 S 0.22596(9) 0.0000 0.16680(14) 0.0786(7) Uani 1 2 d S . . N1 N 0.0000 0.2020(2) 0.0000 0.0630(9) Uani 1 2 d S . . H1A H 0.0552 0.1594 0.0405 0.076 Uiso 0.50 1 calc PR . . H1B H -0.0552 0.1594 -0.0405 0.076 Uiso 0.50 1 calc PR . . C2 C 0.0385(2) 0.2627(3) -0.1433(4) 0.0746(9) Uani 1 1 d . . . H2 H 0.0980 0.3103 -0.1009 0.090 Uiso 1 1 calc R . . F3 F 0.1567(8) 0.0000 0.4597(9) 0.200(5) Uani 0.94(2) 2 d SP . 1 C4 C -0.0504(4) 0.3272(4) -0.2254(6) 0.1136(16) Uani 1 1 d . . . H4A H -0.1087 0.2812 -0.2688 0.170 Uiso 1 1 calc R . . H4B H -0.0232 0.3671 -0.3166 0.170 Uiso 1 1 calc R . . H4C H -0.0776 0.3754 -0.1444 0.170 Uiso 1 1 calc R . . C5 C 0.0836(4) 0.1826(4) -0.2610(6) 0.1098(15) Uani 1 1 d . . . H5A H 0.1429 0.1442 -0.2024 0.165 Uiso 1 1 calc R . . H5B H 0.1099 0.2189 -0.3565 0.165 Uiso 1 1 calc R . . H5C H 0.0267 0.1336 -0.2993 0.165 Uiso 1 1 calc R . . C6 C 0.2468(6) 0.0000 0.3829(10) 0.116(2) Uani 1 2 d SD . . O7 O 0.3302(7) 0.0000 0.1090(10) 0.159(4) Uani 0.898(19) 2 d SP A 3 F9 F 0.2657(7) 0.1001(7) 0.4371(8) 0.200(5) Uani 0.741(14) 1 d PU . 2 O1 O 0.2061(4) 0.1143(4) 0.1427(9) 0.133(3) Uani 0.699(13) 1 d P A 2 F4 F 0.3507(7) 0.0000 0.4303(13) 0.172(7) Uani 0.58(2) 2 d SPDU . 3 O3 O 0.1161(8) 0.0000 0.1290(13) 0.179(6) Uani 0.70(2) 2 d SPU A 1 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 S1 0.0719(9) 0.0786(9) 0.0847(9) 0.000 0.0031(6) 0.000 N1 0.0678(18) 0.0560(15) 0.0649(17) 0.000 0.0030(14) 0.000 C2 0.078(2) 0.0745(18) 0.0708(17) 0.0038(12) 0.0048(13) -0.0180(13) F3 0.233(9) 0.257(10) 0.121(4) 0.000 0.081(5) 0.000 C4 0.130(4) 0.110(3) 0.100(3) 0.032(2) 0.002(3) 0.018(3) C5 0.115(3) 0.131(4) 0.088(2) -0.009(2) 0.035(2) -0.001(3) C6 0.112(5) 0.129(6) 0.103(4) 0.000 -0.018(4) 0.000 O7 0.142(6) 0.174(7) 0.171(7) 0.000 0.082(5) 0.000 F9 0.236(9) 0.215(7) 0.150(5) -0.093(5) 0.021(4) -0.074(6) O1 0.121(4) 0.108(4) 0.167(5) 0.042(3) -0.001(3) 0.030(3) F4 0.143(8) 0.208(12) 0.153(7) 0.000 -0.073(6) 0.000 O3 0.121(7) 0.266(13) 0.141(7) 0.000 -0.036(5) 0.000 _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 S1 O3 1.382(9) . ? S1 O7 1.416(7) . ? S1 O1 1.495(5) 6 ? S1 O1 1.495(5) . ? S1 C6 1.748(8) . ? N1 C2 1.505(3) . ? N1 C2 1.505(3) 2 ? C2 C4 1.498(5) . ? C2 C5 1.536(5) . ? F3 C6 1.326(11) . ? C6 F4 1.323(8) . ? C6 F9 1.370(7) . ? C6 F9 1.370(7) 6 ? 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 S1 O7 148.0(7) . . ? O3 S1 O1 79.6(2) . 6 ? O7 S1 O1 96.0(2) . 6 ? O3 S1 O1 79.6(2) . . ? O7 S1 O1 96.0(2) . . ? O1 S1 O1 156.6(5) 6 . ? O3 S1 C6 106.9(5) . . ? O7 S1 C6 105.1(5) . . ? O1 S1 C6 98.1(3) 6 . ? O1 S1 C6 98.1(3) . . ? C2 N1 C2 117.8(3) . 2 ? C4 C2 N1 110.9(3) . . ? C4 C2 C5 112.8(3) . . ? N1 C2 C5 106.7(3) . . ? F4 C6 F3 135.3(9) . . ? F4 C6 F9 76.5(5) . . ? F3 C6 F9 88.9(5) . . ? F4 C6 F9 76.5(5) . 6 ? F3 C6 F9 88.9(5) . 6 ? F9 C6 F9 138.8(9) . 6 ? F4 C6 S1 111.0(8) . . ? F3 C6 S1 113.7(6) . . ? F9 C6 S1 109.2(4) . . ? F9 C6 S1 109.2(4) 6 . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.664 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 971792' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_p-1 _audit_creation_date 2013-05-28 _audit_creation_method ; Olex2 1.2 (compiled Mar 21 2013 11:17:50, GUI svn.r4446) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C F3 O3 S, C6 H16 N' _chemical_formula_sum 'C7 H16 F3 N O3 S' _chemical_formula_weight 251.27 _chemical_melting_point ? 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.9073(8) _cell_length_b 8.8169(9) _cell_length_c 8.9215(7) _cell_angle_alpha 90.964(7) _cell_angle_beta 93.394(7) _cell_angle_gamma 91.206(8) _cell_volume 620.66(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_temperature 173(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 264 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0435 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7497 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.22 _diffrn_ambient_temperature 173.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2089 _reflns_number_total 2507 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.263 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.110 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0889 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1498P)^2^+0.7006P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2500 _refine_ls_wR_factor_ref 0.2618 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C5(H5), C2(H2) 2.b Secondary CH2 refined with riding coordinates: N2(H2A,H2B) 2.c Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 S1 S 0.65886(12) 0.73294(10) 0.71020(10) 0.0375(4) Uani 1 1 d . . . N2 N 0.5015(4) 0.7162(3) 0.3054(3) 0.0300(7) Uani 1 1 d . . . H2A H 0.4661 0.6164 0.3102 0.036 Uiso 1 1 calc R . . H2B H 0.5441 0.7452 0.4000 0.036 Uiso 1 1 calc R . . O3 O 0.6457(4) 0.8359(3) 0.5876(3) 0.0476(8) Uani 1 1 d . . . C5 C 0.3478(4) 0.8094(4) 0.2680(4) 0.0353(8) Uani 1 1 d . . . H5 H 0.3844 0.9185 0.2637 0.042 Uiso 1 1 calc R . . C6 C 0.2655(6) 0.7621(6) 0.1180(5) 0.0529(11) Uani 1 1 d . . . H6A H 0.3430 0.7844 0.0391 0.079 Uiso 1 1 calc R . . H6B H 0.1608 0.8181 0.0996 0.079 Uiso 1 1 calc R . . H6C H 0.2391 0.6530 0.1174 0.079 Uiso 1 1 calc R . . C7 C 0.8834(5) 0.7384(5) 0.7666(5) 0.0494(10) Uani 1 1 d . . . C8 C 0.2306(5) 0.7919(5) 0.3944(5) 0.0503(11) Uani 1 1 d . . . H8A H 0.1321 0.8560 0.3762 0.075 Uiso 1 1 calc R . . H8B H 0.2908 0.8226 0.4896 0.075 Uiso 1 1 calc R . . H8C H 0.1929 0.6856 0.3993 0.075 Uiso 1 1 calc R . . O2 O 0.5816(6) 0.7846(6) 0.8398(4) 0.0895(16) Uani 1 1 d . . . O1 O 0.6293(5) 0.5789(4) 0.6611(5) 0.0823(14) Uani 1 1 d . . . C2 C 0.6449(4) 0.7234(4) 0.2017(4) 0.0356(8) Uani 1 1 d . . . H2 H 0.5992 0.6972 0.0974 0.043 Uiso 1 1 calc R . . C3 C 0.7216(6) 0.8825(5) 0.2031(6) 0.0533(11) Uani 1 1 d . . . H3A H 0.7606 0.9119 0.3060 0.080 Uiso 1 1 calc R . . H3B H 0.6359 0.9534 0.1656 0.080 Uiso 1 1 calc R . . H3C H 0.8177 0.8849 0.1387 0.080 Uiso 1 1 calc R . . C1 C 0.7720(6) 0.6049(6) 0.2512(6) 0.0542(11) Uani 1 1 d . . . H1A H 0.8122 0.6255 0.3558 0.081 Uiso 1 1 calc R . . H1B H 0.8682 0.6087 0.1870 0.081 Uiso 1 1 calc R . . H1C H 0.7176 0.5039 0.2430 0.081 Uiso 1 1 calc R . . F13 F 0.9179(4) 0.6457(4) 0.8791(4) 0.0697(9) Uani 1 1 d . . . F1 F 0.9298(5) 0.8758(4) 0.8141(5) 0.1074(16) Uani 1 1 d . . . F2 F 0.9739(5) 0.6953(6) 0.6573(4) 0.1110(16) Uani 1 1 d . . . 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 S1 0.0389(6) 0.0375(6) 0.0359(6) -0.0002(4) 0.0023(4) -0.0013(4) N2 0.0311(14) 0.0313(14) 0.0275(14) 0.0001(12) 0.0024(11) -0.0014(11) O3 0.0629(19) 0.0426(15) 0.0357(15) -0.0032(12) -0.0088(13) -0.0018(13) C5 0.0292(17) 0.0311(17) 0.045(2) 0.0001(15) 0.0023(15) -0.0005(13) C6 0.041(2) 0.066(3) 0.051(3) 0.005(2) -0.0069(19) 0.0051(19) C7 0.039(2) 0.056(2) 0.053(2) 0.004(2) -0.0002(19) -0.0046(18) C8 0.040(2) 0.053(2) 0.059(3) -0.006(2) 0.013(2) 0.0032(17) O2 0.074(3) 0.158(4) 0.0403(19) 0.011(2) 0.0148(18) 0.052(3) O1 0.084(3) 0.0406(18) 0.117(3) 0.011(2) -0.034(2) -0.0210(17) C2 0.0323(18) 0.045(2) 0.0296(18) -0.0012(16) 0.0058(14) 0.0002(15) C3 0.046(2) 0.056(3) 0.059(3) 0.007(2) 0.015(2) -0.0121(19) C1 0.041(2) 0.066(3) 0.057(3) 0.005(2) 0.012(2) 0.012(2) F13 0.0665(18) 0.074(2) 0.0667(19) 0.0129(16) -0.0156(15) 0.0125(15) F1 0.100(3) 0.072(2) 0.141(4) 0.015(2) -0.063(3) -0.0373(19) F2 0.056(2) 0.205(5) 0.076(2) 0.017(3) 0.0243(17) 0.035(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 S1 O3 1.434(3) . ? S1 C7 1.816(4) . ? S1 O2 1.412(4) . ? S1 O1 1.430(4) . ? N2 C5 1.505(4) . ? N2 C2 1.506(4) . ? C5 C6 1.502(6) . ? C5 C8 1.509(6) . ? C7 F13 1.325(5) . ? C7 F1 1.314(6) . ? C7 F2 1.300(6) . ? C2 C3 1.516(6) . ? C2 C1 1.518(5) . ? 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 S1 C7 103.6(2) . . ? O2 S1 O3 113.8(2) . . ? O2 S1 C7 103.7(3) . . ? O2 S1 O1 118.6(3) . . ? O1 S1 O3 111.9(2) . . ? O1 S1 C7 103.0(2) . . ? C5 N2 C2 118.1(3) . . ? N2 C5 C8 107.5(3) . . ? C6 C5 N2 110.8(3) . . ? C6 C5 C8 112.8(3) . . ? F13 C7 S1 111.3(3) . . ? F1 C7 S1 109.9(3) . . ? F1 C7 F13 107.0(4) . . ? F2 C7 S1 111.4(4) . . ? F2 C7 F13 106.6(4) . . ? F2 C7 F1 110.6(5) . . ? N2 C2 C3 110.1(3) . . ? N2 C2 C1 107.7(3) . . ? C3 C2 C1 112.9(4) . . ? _database_code_depnum_ccdc_archive 'CCDC 971793'