# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'CIFs.cif' _publ_contact_author_name 'Thomas Gelbrich' _publ_contact_author_address ; Institut f\"ur Pharmazie, Universit\"at Innsbruck, Innrain 52, 6020 Innsbruck, Austria ; _publ_contact_author_email thomas.gelbrich@uibk.ac.at loop_ _publ_author_name T.Gelbrich T.L.Threlfall M.B.Hursthouse #TrackingRef 'CIFs.cif' data_A1_CF3~I _database_code_depnum_ccdc_archive 'CCDC 871342' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 F3 I N2 O2 S' _chemical_formula_sum 'C12 H8 F3 I N2 O2 S' _chemical_formula_weight 428.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5467(6) _cell_length_b 19.1791(10) _cell_length_c 5.7446(2) _cell_angle_alpha 90 _cell_angle_beta 97.251(3) _cell_angle_gamma 90 _cell_volume 1371.29(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6789 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 2.074 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.3456 _exptl_absorpt_correction_T_max 0.9512 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_unetI/netI 0.0403 _diffrn_reflns_number 9282 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _reflns_number_total 2645 _reflns_number_gt 2191 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0398P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0018(3) _refine_ls_number_reflns 2645 _refine_ls_number_parameters 194 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.51 _refine_diff_density_min -0.878 _refine_diff_density_rms 0.104 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.17693(6) 0.11572(4) 1.15289(13) 0.02058(19) Uani 1 1 d . . . I1 I -0.219233(17) 0.156029(11) 0.11407(4) 0.02810(11) Uani 1 1 d . . . O1 O 0.21261(18) 0.07523(12) 1.3586(4) 0.0286(5) Uani 1 1 d . . . O2 O 0.14727(18) 0.18741(11) 1.1866(4) 0.0243(5) Uani 1 1 d . . . N1 N 0.0831(2) 0.07039(12) 1.0101(4) 0.0211(6) Uani 1 1 d . . . N2 N -0.0548(2) 0.05283(13) 0.7181(4) 0.0196(6) Uani 1 1 d D . . H2 H -0.065(3) 0.0145(12) 0.791(5) 0.023 Uiso 1 1 d D . . C1 C 0.2841(2) 0.11795(15) 0.9789(5) 0.0198(6) Uani 1 1 d . . . C6 C 0.3362(3) 0.05570(17) 0.9324(6) 0.0250(7) Uani 1 1 d . . . H6 H 0.313 0.0126 0.99 0.03 Uiso 1 1 calc R . . C5 C 0.4209(3) 0.05766(17) 0.8031(6) 0.0269(7) Uani 1 1 d . . . H5 H 0.4558 0.0157 0.7679 0.032 Uiso 1 1 calc R . . C4 C 0.4555(2) 0.12119(17) 0.7236(5) 0.0237(7) Uani 1 1 d . . . C3 C 0.4044(3) 0.18237(18) 0.7696(6) 0.0254(7) Uani 1 1 d . . . H3 H 0.4288 0.2255 0.7148 0.03 Uiso 1 1 calc R . . C2 C 0.3177(2) 0.18089(17) 0.8950(5) 0.0234(7) Uani 1 1 d . . . H2A H 0.2812 0.2228 0.9238 0.028 Uiso 1 1 calc R . . C7 C 0.0246(2) 0.09580(15) 0.8156(5) 0.0190(6) Uani 1 1 d . . . C8 C 0.0349(3) 0.16011(15) 0.6988(6) 0.0199(7) Uani 1 1 d . . . H8 H 0.0902 0.1918 0.7567 0.024 Uiso 1 1 calc R . . C9 C -0.0340(2) 0.17668(17) 0.5042(6) 0.0221(7) Uani 1 1 d . . . H9 H -0.0272 0.2203 0.4289 0.027 Uiso 1 1 calc R . . C10 C -0.1148(3) 0.13011(17) 0.4137(5) 0.0221(7) Uani 1 1 d . . . C11 C -0.1235(3) 0.06796(15) 0.5249(5) 0.0215(7) Uani 1 1 d . . . H11 H -0.1777 0.0355 0.4667 0.026 Uiso 1 1 calc R . . C12 C 0.5463(3) 0.1234(2) 0.5782(6) 0.0318(8) Uani 1 1 d . . . F1 F 0.60853(17) 0.18004(13) 0.6243(4) 0.0455(6) Uani 1 1 d . . . F2 F 0.61138(17) 0.06838(12) 0.6093(4) 0.0468(6) Uani 1 1 d . . . F3 F 0.51109(17) 0.12559(14) 0.3482(4) 0.0510(6) 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 0.0246(4) 0.0148(4) 0.0220(4) 0.0006(3) 0.0017(3) -0.0032(3) I1 0.03017(16) 0.02798(16) 0.02511(15) 0.00526(8) -0.00061(10) 0.00177(9) O1 0.0341(13) 0.0260(13) 0.0240(12) 0.0044(9) -0.0030(10) -0.0083(10) O2 0.0332(13) 0.0129(11) 0.0276(12) -0.0027(9) 0.0069(10) 0.0003(10) N1 0.0236(14) 0.0131(13) 0.0258(14) 0.0015(11) 0.0001(11) -0.0038(11) N2 0.0227(14) 0.0106(13) 0.0252(14) 0.0037(10) 0.0023(11) -0.0021(11) C1 0.0217(16) 0.0175(16) 0.0188(15) 0.0010(12) -0.0032(13) 0.0022(13) C6 0.0277(18) 0.0175(16) 0.0289(17) -0.0008(13) -0.0007(14) 0.0002(14) C5 0.0273(18) 0.0222(18) 0.0300(17) -0.0068(13) -0.0013(14) 0.0046(14) C4 0.0193(16) 0.0284(19) 0.0219(16) -0.0023(13) -0.0032(13) 0.0010(14) C3 0.0259(17) 0.0195(17) 0.0300(18) 0.0053(14) 0.0008(14) 0.0000(14) C2 0.0245(17) 0.0149(15) 0.0294(17) -0.0002(13) -0.0019(14) -0.0008(13) C7 0.0176(15) 0.0141(16) 0.0259(16) 0.0001(12) 0.0055(13) 0.0007(12) C8 0.0216(17) 0.0162(16) 0.0229(17) 0.0006(12) 0.0068(14) -0.0017(13) C9 0.0238(17) 0.0161(15) 0.0275(17) 0.0052(13) 0.0074(14) 0.0017(13) C10 0.0248(17) 0.0185(16) 0.0235(17) 0.0035(13) 0.0050(13) 0.0034(13) C11 0.0250(16) 0.0156(16) 0.0239(16) -0.0008(12) 0.0033(14) -0.0004(13) C12 0.0282(19) 0.039(2) 0.0273(19) -0.0025(15) 0.0016(15) 0.0037(17) F1 0.0333(12) 0.0515(14) 0.0541(14) -0.0123(11) 0.0144(10) -0.0147(11) F2 0.0350(12) 0.0542(15) 0.0530(14) 0.0000(10) 0.0127(11) 0.0155(11) F3 0.0395(13) 0.0917(18) 0.0212(11) -0.0028(12) 0.0016(10) 0.0017(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.438(2) . ? S1 O2 1.444(2) . ? S1 N1 1.603(3) . ? S1 C1 1.774(3) . ? I1 C10 2.087(3) . ? N1 C7 1.348(4) . ? N2 C11 1.349(4) . ? N2 C7 1.358(4) . ? N2 H2 0.864(18) . ? C1 C2 1.385(4) . ? C1 C6 1.403(4) . ? C6 C5 1.372(5) . ? C6 H6 0.95 . ? C5 C4 1.390(5) . ? C5 H5 0.95 . ? C4 C3 1.379(5) . ? C4 C12 1.496(4) . ? C3 C2 1.379(4) . ? C3 H3 0.95 . ? C2 H2A 0.95 . ? C7 C8 1.418(4) . ? C8 C9 1.362(5) . ? C8 H8 0.95 . ? C9 C10 1.401(5) . ? C9 H9 0.95 . ? C10 C11 1.363(4) . ? C11 H11 0.95 . ? C12 F2 1.333(4) . ? C12 F3 1.340(4) . ? C12 F1 1.344(4) . ? 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 O1 S1 O2 117.56(13) . . ? O1 S1 N1 105.07(13) . . ? O2 S1 N1 113.57(13) . . ? O1 S1 C1 107.26(14) . . ? O2 S1 C1 106.21(13) . . ? N1 S1 C1 106.54(14) . . ? C7 N1 S1 121.1(2) . . ? C11 N2 C7 124.7(2) . . ? C11 N2 H2 118(2) . . ? C7 N2 H2 117(2) . . ? C2 C1 C6 120.4(3) . . ? C2 C1 S1 120.2(2) . . ? C6 C1 S1 119.4(2) . . ? C5 C6 C1 119.4(3) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 C12 119.2(3) . . ? C5 C4 C12 120.0(3) . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? N1 C7 N2 114.6(2) . . ? N1 C7 C8 129.3(3) . . ? N2 C7 C8 116.0(3) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 118.7(3) . . ? C11 C10 I1 121.0(2) . . ? C9 C10 I1 120.2(2) . . ? N2 C11 C10 119.5(3) . . ? N2 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? F2 C12 F3 106.0(3) . . ? F2 C12 F1 106.4(3) . . ? F3 C12 F1 106.3(3) . . ? F2 C12 C4 113.5(3) . . ? F3 C12 C4 111.9(3) . . ? F1 C12 C4 112.2(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.864(18) 2.018(19) 2.879(3) 175(3) 3_557 #----------------------------------------------------------------------------# data_A1_I~I _database_code_depnum_ccdc_archive 'CCDC 871343' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 I2 N2 O2 S' _chemical_formula_sum 'C11 H8 I2 N2 O2 S' _chemical_formula_weight 486.05 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7165(8) _cell_length_b 19.5032(14) _cell_length_c 5.6759(3) _cell_angle_alpha 90 _cell_angle_beta 99.204(4) _cell_angle_gamma 90 _cell_volume 1389.57(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4800 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 27.48 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.671 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.4551 _exptl_absorpt_correction_T_max 0.8 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_unetI/netI 0.063 _diffrn_reflns_number 9542 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2707 _reflns_number_gt 1565 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2707 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.732 _refine_diff_density_min -0.969 _refine_diff_density_rms 0.112 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.17887(16) 0.11568(9) 1.1741(3) 0.0606(5) Uani 1 1 d . . . I1 I 0.56583(5) 0.12801(4) 0.52270(11) 0.0966(3) Uani 1 1 d . . . I2 I -0.22417(4) 0.15212(3) 0.10421(9) 0.0752(2) Uani 1 1 d . . . O1 O 0.2139(4) 0.0749(3) 1.3834(8) 0.0764(15) Uani 1 1 d . . . O2 O 0.1488(4) 0.1854(2) 1.2087(8) 0.0689(13) Uani 1 1 d . . . N1 N 0.0843(4) 0.0718(3) 1.0228(9) 0.0577(14) Uani 1 1 d . . . N2 N -0.0531(4) 0.0527(3) 0.7230(9) 0.0520(13) Uani 1 1 d . . . H2 H -0.0583 0.0135 0.7896 0.11(3) Uiso 1 1 calc R . . C1 C 0.2835(5) 0.1181(3) 1.0021(11) 0.0522(16) Uani 1 1 d . . . C6 C 0.3348(6) 0.0591(4) 0.9539(12) 0.0663(19) Uani 1 1 d . . . H6 H 0.3153 0.0175 1.0141 0.08 Uiso 1 1 calc R . . C5 C 0.4145(7) 0.0610(4) 0.8180(13) 0.077(2) Uani 1 1 d . . . H5 H 0.4467 0.0206 0.7795 0.093 Uiso 1 1 calc R . . C4 C 0.4465(6) 0.1228(4) 0.7392(12) 0.0632(19) Uani 1 1 d . . . C3 C 0.3978(6) 0.1811(4) 0.7888(12) 0.0668(19) Uani 1 1 d . . . H3 H 0.4206 0.2231 0.7376 0.08 Uiso 1 1 calc R . . C2 C 0.3146(6) 0.1786(3) 0.9149(12) 0.0615(18) Uani 1 1 d . . . H2A H 0.2788 0.2188 0.9413 0.074 Uiso 1 1 calc R . . C7 C 0.0231(5) 0.0956(3) 0.8229(11) 0.0463(15) Uani 1 1 d . . . C8 C 0.0300(6) 0.1595(3) 0.7071(13) 0.0586(18) Uani 1 1 d . . . H8 H 0.0825 0.1907 0.7683 0.07 Uiso 1 1 calc R . . C9 C -0.0394(6) 0.1752(4) 0.5082(13) 0.0612(19) Uani 1 1 d . . . H9 H -0.0352 0.2179 0.4372 0.073 Uiso 1 1 calc R . . C10 C -0.1165(6) 0.1289(3) 0.4081(12) 0.0567(17) Uani 1 1 d . . . C11 C -0.1224(6) 0.0674(3) 0.5237(12) 0.0613(18) Uani 1 1 d . . . H11 H -0.1746 0.0358 0.4641 0.074 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0683(13) 0.0515(12) 0.0621(11) 0.0011(9) 0.0105(9) -0.0064(10) I1 0.0674(4) 0.1394(6) 0.0851(4) -0.0156(3) 0.0182(3) 0.0100(3) I2 0.0720(4) 0.0863(4) 0.0665(3) 0.0146(3) 0.0088(3) 0.0069(3) O1 0.097(4) 0.072(3) 0.056(3) 0.010(2) 0.000(3) -0.017(3) O2 0.086(4) 0.049(3) 0.076(3) -0.014(2) 0.023(3) -0.001(3) N1 0.051(4) 0.052(3) 0.068(4) 0.007(3) 0.006(3) -0.007(3) N2 0.047(4) 0.046(3) 0.063(3) 0.005(3) 0.009(3) -0.003(3) C1 0.052(4) 0.047(4) 0.054(4) -0.005(3) -0.001(3) 0.000(3) C6 0.073(5) 0.050(5) 0.075(5) 0.004(4) 0.009(4) 0.006(4) C5 0.080(6) 0.069(6) 0.077(5) -0.005(4) -0.003(4) 0.024(5) C4 0.061(5) 0.074(5) 0.054(4) -0.007(4) 0.004(3) -0.002(4) C3 0.066(5) 0.064(5) 0.071(5) 0.008(4) 0.013(4) 0.001(4) C2 0.067(5) 0.046(4) 0.072(5) 0.006(3) 0.012(4) -0.002(4) C7 0.044(4) 0.043(4) 0.053(4) 0.002(3) 0.014(3) 0.002(3) C8 0.062(5) 0.045(4) 0.071(5) 0.008(3) 0.016(4) -0.004(4) C9 0.065(5) 0.045(4) 0.076(5) 0.013(3) 0.021(4) 0.007(4) C10 0.063(5) 0.048(4) 0.061(4) 0.002(3) 0.016(3) 0.005(4) C11 0.063(5) 0.053(4) 0.069(5) 0.003(4) 0.016(4) -0.002(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.435(5) . ? S1 O1 1.439(5) . ? S1 N1 1.608(6) . ? S1 C1 1.772(7) . ? I1 C4 2.103(7) . ? I2 C10 2.073(7) . ? N1 C7 1.351(8) . ? N2 C7 1.336(7) . ? N2 C11 1.349(8) . ? N2 H2 0.86 . ? C1 C2 1.363(9) . ? C1 C6 1.371(9) . ? C6 C5 1.369(10) . ? C6 H6 0.93 . ? C5 C4 1.369(10) . ? C5 H5 0.93 . ? C4 C3 1.347(10) . ? C3 C2 1.369(9) . ? C3 H3 0.93 . ? C2 H2A 0.93 . ? C7 C8 1.418(9) . ? C8 C9 1.352(10) . ? C8 H8 0.93 . ? C9 C10 1.386(10) . ? C9 H9 0.93 . ? C10 C11 1.375(9) . ? C11 H11 0.93 . ? 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 O2 S1 O1 117.7(3) . . ? O2 S1 N1 112.6(3) . . ? O1 S1 N1 104.7(3) . . ? O2 S1 C1 106.9(3) . . ? O1 S1 C1 108.0(3) . . ? N1 S1 C1 106.5(3) . . ? C7 N1 S1 123.1(5) . . ? C7 N2 C11 123.7(6) . . ? C7 N2 H2 118.1 . . ? C11 N2 H2 118.1 . . ? C2 C1 C6 118.6(7) . . ? C2 C1 S1 120.7(5) . . ? C6 C1 S1 120.7(5) . . ? C5 C6 C1 120.6(7) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C6 C5 C4 119.6(7) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C3 C4 C5 120.3(7) . . ? C3 C4 I1 118.7(6) . . ? C5 C4 I1 120.9(6) . . ? C4 C3 C2 119.9(7) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C1 C2 C3 121.0(7) . . ? C1 C2 H2A 119.5 . . ? C3 C2 H2A 119.5 . . ? N2 C7 N1 115.0(5) . . ? N2 C7 C8 116.6(6) . . ? N1 C7 C8 128.4(6) . . ? C9 C8 C7 120.4(7) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 121.3(6) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 117.5(7) . . ? C11 C10 I2 120.6(6) . . ? C9 C10 I2 121.9(5) . . ? N2 C11 C10 120.5(7) . . ? N2 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.86 2.03 2.884(8) 171.5 3_557 #----------------------------------------------------------------------------# data_A1_Br~I _database_code_depnum_ccdc_archive 'CCDC 871344' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 Br I N2 O2 S' _chemical_formula_sum 'C11 H8 Br I N2 O2 S' _chemical_formula_weight 439.06 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3761(5) _cell_length_b 19.3231(7) _cell_length_c 5.5652(2) _cell_angle_alpha 90 _cell_angle_beta 98.8240(10) _cell_angle_gamma 90 _cell_volume 1315.14(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8382 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 2.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.626 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.1753 _exptl_absorpt_correction_T_max 0.8958 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.053 _diffrn_reflns_av_unetI/netI 0.0481 _diffrn_reflns_number 8870 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 2530 _reflns_number_gt 2216 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0432P)^2^+1.0979P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2530 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0810 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0 '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 0.006 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.18139(8) 0.11467(5) 1.15919(17) 0.0188(2) Uani 1 1 d . . . I1 I -0.23327(2) 0.153704(14) 0.07548(5) 0.02561(14) Uani 1 1 d . . . Br1 Br 0.56667(4) 0.12552(3) 0.50758(8) 0.03522(16) Uani 1 1 d . . . O1 O 0.2183(2) 0.07362(15) 1.3725(5) 0.0277(7) Uani 1 1 d . . . O2 O 0.1516(2) 0.18575(14) 1.1947(5) 0.0236(6) Uani 1 1 d . . . N1 N 0.0841(3) 0.06982(16) 1.0077(6) 0.0202(7) Uani 1 1 d . . . N2 N -0.0591(3) 0.05250(16) 0.7038(6) 0.0199(7) Uani 1 1 d D . . H2 H -0.0648 0.0121 0.7736 0.024 Uiso 1 1 calc RD . . C1 C 0.2895(3) 0.11662(19) 0.9835(7) 0.0188(8) Uani 1 1 d . . . C6 C 0.3430(3) 0.0561(2) 0.9398(7) 0.0236(9) Uani 1 1 d . . . H6 H 0.3229 0.0135 1.0062 0.028 Uiso 1 1 calc R . . C5 C 0.4264(3) 0.0579(2) 0.7979(7) 0.0256(9) Uani 1 1 d . . . H5 H 0.4629 0.0167 0.7631 0.031 Uiso 1 1 calc R . . C4 C 0.4549(3) 0.1215(2) 0.7085(7) 0.0238(9) Uani 1 1 d . . . C3 C 0.4050(3) 0.1817(2) 0.7569(8) 0.0252(9) Uani 1 1 d . . . H3 H 0.4284 0.2246 0.6989 0.030 Uiso 1 1 calc R . . C2 C 0.3200(3) 0.1798(2) 0.8908(7) 0.0221(8) Uani 1 1 d . . . H2A H 0.2823 0.2210 0.9200 0.026 Uiso 1 1 calc R . . C7 C 0.0224(3) 0.09555(18) 0.8073(7) 0.0159(7) Uani 1 1 d . . . C8 C 0.0300(3) 0.15949(19) 0.6874(8) 0.0196(8) Uani 1 1 d . . . H8 H 0.0859 0.1914 0.7486 0.024 Uiso 1 1 calc R . . C9 C -0.0419(3) 0.1757(2) 0.4853(7) 0.0210(8) Uani 1 1 d . . . H9 H -0.0363 0.2191 0.4085 0.025 Uiso 1 1 calc R . . C10 C -0.1240(3) 0.1294(2) 0.3886(7) 0.0199(8) Uani 1 1 d . . . C11 C -0.1311(3) 0.0668(2) 0.5045(7) 0.0206(8) Uani 1 1 d . . . H11 H -0.1862 0.0343 0.4440 0.025 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0243(5) 0.0134(5) 0.0191(5) -0.0002(3) 0.0042(4) -0.0037(4) I1 0.0272(2) 0.0275(2) 0.0219(2) 0.00584(9) 0.00290(12) 0.00198(11) Br1 0.0269(3) 0.0482(3) 0.0323(3) -0.0054(2) 0.01017(19) 0.0024(2) O1 0.0373(17) 0.0245(16) 0.0192(15) 0.0036(11) -0.0024(12) -0.0087(13) O2 0.0292(16) 0.0165(14) 0.0263(16) -0.0041(11) 0.0080(12) -0.0032(12) N1 0.0245(18) 0.0140(16) 0.0215(17) -0.0025(12) 0.0010(13) -0.0037(13) N2 0.0230(17) 0.0136(16) 0.0241(18) 0.0033(13) 0.0072(13) -0.0030(13) C1 0.021(2) 0.017(2) 0.018(2) 0.0005(14) 0.0021(15) -0.0022(15) C6 0.027(2) 0.016(2) 0.025(2) 0.0002(15) -0.0031(16) 0.0007(16) C5 0.026(2) 0.021(2) 0.028(2) -0.0056(16) -0.0015(17) 0.0091(17) C4 0.021(2) 0.029(2) 0.020(2) -0.0033(16) 0.0009(16) 0.0040(18) C3 0.025(2) 0.020(2) 0.030(2) 0.0048(16) 0.0033(17) 0.0008(17) C2 0.022(2) 0.0140(19) 0.030(2) 0.0013(15) 0.0041(16) 0.0005(16) C7 0.0191(19) 0.0113(17) 0.0194(19) 0.0000(13) 0.0096(15) 0.0012(15) C8 0.020(2) 0.0145(19) 0.025(2) -0.0011(14) 0.0060(16) -0.0025(15) C9 0.025(2) 0.0132(18) 0.028(2) 0.0049(15) 0.0126(17) 0.0022(16) C10 0.024(2) 0.0184(19) 0.017(2) 0.0042(15) 0.0034(15) 0.0015(16) C11 0.019(2) 0.022(2) 0.021(2) -0.0034(15) 0.0029(15) -0.0005(16) _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 O1 1.442(3) . ? S1 O2 1.443(3) . ? S1 N1 1.612(3) . ? S1 C1 1.775(4) . ? I1 C10 2.089(4) . ? Br1 C4 1.909(4) . ? N1 C7 1.347(5) . ? N2 C11 1.341(5) . ? N2 C7 1.364(5) . ? N2 H2 0.8800 . ? C1 C6 1.384(5) . ? C1 C2 1.398(5) . ? C6 C5 1.393(6) . ? C6 H6 0.9500 . ? C5 C4 1.392(6) . ? C5 H5 0.9500 . ? C4 C3 1.365(6) . ? C3 C2 1.380(6) . ? C3 H3 0.9500 . ? C2 H2A 0.9500 . ? C7 C8 1.414(5) . ? C8 C9 1.360(6) . ? C8 H8 0.9500 . ? C9 C10 1.397(6) . ? C9 H9 0.9500 . ? C10 C11 1.379(5) . ? C11 H11 0.9500 . ? 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 O1 S1 O2 117.77(17) . . ? O1 S1 N1 104.57(17) . . ? O2 S1 N1 113.40(17) . . ? O1 S1 C1 107.13(18) . . ? O2 S1 C1 106.56(17) . . ? N1 S1 C1 106.80(17) . . ? C7 N1 S1 121.2(3) . . ? C11 N2 C7 125.3(3) . . ? C11 N2 H2 117.4 . . ? C7 N2 H2 117.4 . . ? C6 C1 C2 120.7(4) . . ? C6 C1 S1 120.0(3) . . ? C2 C1 S1 119.4(3) . . ? C1 C6 C5 119.6(4) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C4 C5 C6 118.4(4) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C3 C4 C5 122.4(4) . . ? C3 C4 Br1 118.1(3) . . ? C5 C4 Br1 119.5(3) . . ? C4 C3 C2 119.2(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? N1 C7 N2 114.4(3) . . ? N1 C7 C8 130.0(4) . . ? N2 C7 C8 115.6(4) . . ? C9 C8 C7 120.5(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 121.1(4) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 I1 120.5(3) . . ? C9 C10 I1 121.1(3) . . ? N2 C11 C10 119.1(4) . . ? N2 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.88 2.03 2.901(4) 168.5 3_557 _refine_diff_density_max 0.819 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.141 #----------------------------------------------------------------------------# data_A1_Cl~I _database_code_depnum_ccdc_archive 'CCDC 871345' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 Cl I N2 O2 S' _chemical_formula_sum 'C11 H8 Cl I N2 O2 S' _chemical_formula_weight 394.6 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1910(5) _cell_length_b 19.2471(7) _cell_length_c 5.5793(2) _cell_angle_alpha 90 _cell_angle_beta 98.4410(10) _cell_angle_gamma 90 _cell_volume 1294.95(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5647 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.04 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 2.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.3109 _exptl_absorpt_correction_T_max 0.9455 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0455 _diffrn_reflns_number 7515 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.97 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _reflns_number_total 2494 _reflns_number_gt 2197 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0015P)^2^+1.0860P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0029(3) _refine_ls_number_reflns 2494 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.027 _refine_ls_wR_factor_ref 0.0601 _refine_ls_wR_factor_gt 0.0581 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.499 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.101 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.18443(6) 0.11477(4) 1.15260(13) 0.01767(18) Uani 1 1 d . . . I1 I -0.235748(18) 0.154727(11) 0.07819(4) 0.02418(11) Uani 1 1 d . . . Cl1 Cl 0.56842(8) 0.12167(6) 0.52039(17) 0.0384(2) Uani 1 1 d . . . O1 O 0.22166(19) 0.07395(12) 1.3657(4) 0.0262(5) Uani 1 1 d . . . O2 O 0.15437(18) 0.18618(11) 1.1878(4) 0.0224(5) Uani 1 1 d . . . N1 N 0.0856(2) 0.06975(13) 1.0051(5) 0.0184(6) Uani 1 1 d . . . N2 N -0.0600(2) 0.05247(13) 0.7048(4) 0.0166(5) Uani 1 1 d D . . H2 H -0.067(3) 0.0141(12) 0.780(5) 0.02 Uiso 1 1 d D . . C1 C 0.2935(3) 0.11640(16) 0.9747(5) 0.0172(6) Uani 1 1 d . . . C6 C 0.3464(3) 0.05469(16) 0.9290(6) 0.0217(7) Uani 1 1 d . . . H6 H 0.3247 0.0121 0.9941 0.026 Uiso 1 1 calc R . . C5 C 0.4312(3) 0.05584(18) 0.7876(6) 0.0268(8) Uani 1 1 d . . . H5 H 0.4665 0.014 0.7507 0.032 Uiso 1 1 calc R . . C4 C 0.4636(3) 0.11923(18) 0.7010(6) 0.0244(7) Uani 1 1 d . . . C3 C 0.4131(3) 0.18066(17) 0.7512(6) 0.0233(7) Uani 1 1 d . . . H3 H 0.4377 0.2236 0.6943 0.028 Uiso 1 1 calc R . . C2 C 0.3263(3) 0.17909(17) 0.8853(6) 0.0210(7) Uani 1 1 d . . . H2A H 0.2893 0.2209 0.9161 0.025 Uiso 1 1 calc R . . C7 C 0.0231(2) 0.09546(14) 0.8038(5) 0.0151(6) Uani 1 1 d . . . C8 C 0.0324(3) 0.15934(15) 0.6846(6) 0.0173(7) Uani 1 1 d . . . H8 H 0.0898 0.1909 0.7448 0.021 Uiso 1 1 calc R . . C9 C -0.0406(3) 0.17608(16) 0.4827(6) 0.0183(7) Uani 1 1 d . . . H9 H -0.0338 0.2193 0.4042 0.022 Uiso 1 1 calc R . . C10 C -0.1257(3) 0.12976(16) 0.3905(5) 0.0186(7) Uani 1 1 d . . . C11 C -0.1336(3) 0.06783(16) 0.5050(5) 0.0179(7) Uani 1 1 d . . . H11 H -0.1902 0.0357 0.4454 0.021 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0204(4) 0.0143(4) 0.0178(4) 0.0008(3) 0.0008(3) -0.0035(3) I1 0.02412(16) 0.02781(16) 0.01978(15) 0.00538(8) 0.00048(9) 0.00141(9) Cl1 0.0258(5) 0.0564(6) 0.0353(5) -0.0053(5) 0.0121(4) 0.0018(4) O1 0.0320(14) 0.0262(13) 0.0184(11) 0.0032(10) -0.0035(10) -0.0077(10) O2 0.0259(13) 0.0160(11) 0.0265(12) -0.0039(9) 0.0075(10) -0.0019(9) N1 0.0185(14) 0.0149(13) 0.0210(14) 0.0021(11) 0.0006(11) -0.0038(11) N2 0.0189(14) 0.0117(13) 0.0192(13) 0.0031(10) 0.0029(10) -0.0012(11) C1 0.0170(16) 0.0169(15) 0.0159(15) -0.0009(12) -0.0029(12) -0.0020(13) C6 0.0219(18) 0.0157(16) 0.0254(17) 0.0012(13) -0.0037(13) 0.0009(13) C5 0.0233(19) 0.0262(18) 0.0285(18) -0.0050(14) -0.0038(14) 0.0097(15) C4 0.0147(17) 0.037(2) 0.0209(17) -0.0024(15) -0.0006(13) 0.0016(15) C3 0.0206(18) 0.0213(17) 0.0276(18) 0.0051(14) 0.0018(14) -0.0024(14) C2 0.0200(18) 0.0158(16) 0.0264(18) 0.0002(13) 0.0014(13) -0.0003(13) C7 0.0137(16) 0.0132(15) 0.0192(15) -0.0008(12) 0.0058(12) -0.0006(12) C8 0.0166(17) 0.0135(15) 0.0221(17) -0.0014(12) 0.0042(13) -0.0020(12) C9 0.0214(17) 0.0136(15) 0.0216(16) 0.0034(13) 0.0091(13) 0.0017(13) C10 0.0185(17) 0.0198(16) 0.0178(16) 0.0015(13) 0.0035(12) 0.0029(13) C11 0.0170(16) 0.0179(16) 0.0183(15) -0.0018(12) 0.0012(12) -0.0009(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.442(2) . ? S1 O2 1.443(2) . ? S1 N1 1.609(3) . ? S1 C1 1.772(3) . ? I1 C10 2.093(3) . ? Cl1 C4 1.740(3) . ? N1 C7 1.355(4) . ? N2 C11 1.357(4) . ? N2 C7 1.361(4) . ? N2 H2 0.862(18) . ? C1 C2 1.387(4) . ? C1 C6 1.393(4) . ? C6 C5 1.390(5) . ? C6 H6 0.95 . ? C5 C4 1.391(5) . ? C5 H5 0.95 . ? C4 C3 1.381(5) . ? C3 C2 1.382(5) . ? C3 H3 0.95 . ? C2 H2A 0.95 . ? C7 C8 1.410(4) . ? C8 C9 1.368(5) . ? C8 H8 0.95 . ? C9 C10 1.407(4) . ? C9 H9 0.95 . ? C10 C11 1.362(4) . ? C11 H11 0.95 . ? 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 O1 S1 O2 117.54(13) . . ? O1 S1 N1 104.47(13) . . ? O2 S1 N1 113.34(13) . . ? O1 S1 C1 107.48(14) . . ? O2 S1 C1 106.59(14) . . ? N1 S1 C1 106.87(14) . . ? C7 N1 S1 121.0(2) . . ? C11 N2 C7 124.3(3) . . ? C11 N2 H2 119(2) . . ? C7 N2 H2 116(2) . . ? C2 C1 C6 120.7(3) . . ? C2 C1 S1 119.8(2) . . ? C6 C1 S1 119.5(2) . . ? C5 C6 C1 119.6(3) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C6 C5 C4 119.0(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C3 C4 C5 121.5(3) . . ? C3 C4 Cl1 118.8(3) . . ? C5 C4 Cl1 119.7(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? N1 C7 N2 114.1(2) . . ? N1 C7 C8 129.4(3) . . ? N2 C7 C8 116.5(3) . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 118.8(3) . . ? C11 C10 I1 120.7(2) . . ? C9 C10 I1 120.5(2) . . ? N2 C11 C10 119.5(3) . . ? N2 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.862(18) 2.040(19) 2.898(3) 173(3) 3_557 #----------------------------------------------------------------------------# data_A1_F~I_alpha _database_code_depnum_ccdc_archive 'CCDC 871346' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H8 F I N2 O2 S' _chemical_formula_sum 'C11 H8 F I N2 O2 S' _chemical_formula_weight 378.15 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2100(3) _cell_length_b 18.4797(4) _cell_length_c 6.0146(2) _cell_angle_alpha 90 _cell_angle_beta 97.104(2) _cell_angle_gamma 90 _cell_volume 1236.40(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7766 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 2.032 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.5980 _exptl_absorpt_correction_T_max 0.9216 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_unetI/netI 0.0299 _diffrn_reflns_number 11152 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 2403 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0054P)^2^+4.2451P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0017(4) _refine_ls_number_reflns 2403 _refine_ls_number_parameters 168 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.024 _refine_ls_wR_factor_ref 0.0537 _refine_ls_wR_factor_gt 0.0522 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.388 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.086 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' I I -0.4742 1.8119 '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' 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 0.21124(6) 0.11362(4) 1.12001(11) 0.01927(16) Uani 1 1 d . . . I1 I -0.227995(19) 0.157828(11) 0.12605(3) 0.02848(10) Uani 1 1 d . . . F1 F 0.6041(2) 0.11539(16) 0.5643(4) 0.0608(7) Uani 1 1 d . . . O1 O 0.2544(2) 0.07044(11) 1.3134(3) 0.0274(5) Uani 1 1 d . . . O2 O 0.1809(2) 0.18815(10) 1.1575(3) 0.0257(5) Uani 1 1 d . . . N1 N 0.1013(2) 0.06801(12) 0.9931(4) 0.0200(5) Uani 1 1 d . . . N2 N -0.0569(2) 0.05204(12) 0.7190(4) 0.0176(5) Uani 1 1 d D . . H2 H -0.071(3) 0.0155(13) 0.797(5) 0.024(9) Uiso 1 1 d D . . C1 C 0.3263(3) 0.11492(15) 0.9432(5) 0.0200(6) Uani 1 1 d . . . C6 C 0.3719(3) 0.04968(16) 0.8756(5) 0.0267(7) Uani 1 1 d . . . H6 H 0.3386 0.0052 0.9178 0.032 Uiso 1 1 calc R . . C5 C 0.4659(3) 0.04959(19) 0.7468(5) 0.0348(8) Uani 1 1 d . . . H5 H 0.4981 0.0055 0.6992 0.042 Uiso 1 1 calc R . . C4 C 0.5113(3) 0.1150(2) 0.6897(5) 0.0372(8) Uani 1 1 d . . . C3 C 0.4682(3) 0.1803(2) 0.7540(6) 0.0343(8) Uani 1 1 d . . . H3 H 0.5027 0.2244 0.7125 0.041 Uiso 1 1 calc R . . C2 C 0.3732(3) 0.18023(16) 0.8805(5) 0.0261(6) Uani 1 1 d . . . H2A H 0.3403 0.2246 0.9242 0.031 Uiso 1 1 calc R . . C7 C 0.0379(2) 0.09358(14) 0.8036(5) 0.0170(5) Uani 1 1 d . . . C8 C 0.0582(3) 0.15747(14) 0.6819(5) 0.0190(6) Uani 1 1 d . . . H8 H 0.1236 0.1884 0.7327 0.023 Uiso 1 1 calc R . . C9 C -0.0167(3) 0.17439(15) 0.4914(5) 0.0207(6) Uani 1 1 d . . . H9 H -0.0028 0.2171 0.4107 0.025 Uiso 1 1 calc R . . C10 C -0.1134(3) 0.12954(15) 0.4145(5) 0.0205(6) Uani 1 1 d . . . C11 C -0.1325(3) 0.06802(15) 0.5324(5) 0.0193(6) Uani 1 1 d . . . H11 H -0.1981 0.037 0.4836 0.023 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0232(4) 0.0147(3) 0.0196(3) 0.0008(3) 0.0016(3) -0.0027(3) I1 0.03476(15) 0.02707(13) 0.02226(13) 0.00522(8) -0.00191(8) 0.00012(8) F1 0.0367(13) 0.101(2) 0.0492(14) 0.0147(13) 0.0230(11) 0.0143(13) O1 0.0342(12) 0.0250(11) 0.0215(10) 0.0070(9) -0.0026(9) -0.0078(9) O2 0.0335(12) 0.0157(10) 0.0290(11) -0.0046(8) 0.0083(9) 0.0003(9) N1 0.0214(12) 0.0154(11) 0.0227(12) 0.0026(9) 0.0009(10) -0.0041(9) N2 0.0196(12) 0.0128(11) 0.0209(12) 0.0035(9) 0.0047(9) -0.0004(9) C1 0.0193(14) 0.0206(14) 0.0191(13) 0.0007(11) -0.0020(11) -0.0004(11) C6 0.0319(17) 0.0234(15) 0.0234(15) -0.0023(12) -0.0020(12) 0.0044(12) C5 0.040(2) 0.0408(19) 0.0233(15) -0.0038(14) 0.0008(14) 0.0162(15) C4 0.0224(17) 0.064(2) 0.0258(16) 0.0089(16) 0.0051(13) 0.0112(16) C3 0.0228(17) 0.0419(19) 0.0379(18) 0.0140(15) 0.0026(14) -0.0030(14) C2 0.0228(16) 0.0240(15) 0.0307(16) 0.0067(12) -0.0003(12) -0.0010(12) C7 0.0171(14) 0.0144(12) 0.0204(13) 0.0005(10) 0.0055(11) 0.0021(10) C8 0.0188(14) 0.0147(13) 0.0239(14) 0.0012(11) 0.0045(11) 0.0002(11) C9 0.0248(16) 0.0161(13) 0.0231(14) 0.0028(11) 0.0103(12) 0.0022(11) C10 0.0223(15) 0.0203(14) 0.0192(13) 0.0024(11) 0.0039(11) 0.0041(11) C11 0.0197(14) 0.0184(13) 0.0199(13) -0.0002(11) 0.0032(11) 0.0005(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.443(2) . ? S1 O1 1.444(2) . ? S1 N1 1.606(2) . ? S1 C1 1.770(3) . ? I1 C10 2.094(3) . ? F1 C4 1.359(4) . ? N1 C7 1.352(4) . ? N2 C11 1.353(4) . ? N2 C7 1.357(4) . ? N2 H2 0.850(18) . ? C1 C2 1.387(4) . ? C1 C6 1.390(4) . ? C6 C5 1.383(5) . ? C6 H6 0.95 . ? C5 C4 1.371(5) . ? C5 H5 0.95 . ? C4 C3 1.373(5) . ? C3 C2 1.383(5) . ? C3 H3 0.95 . ? C2 H2A 0.95 . ? C7 C8 1.422(4) . ? C8 C9 1.371(4) . ? C8 H8 0.95 . ? C9 C10 1.397(4) . ? C9 H9 0.95 . ? C10 C11 1.370(4) . ? C11 H11 0.95 . ? 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 O2 S1 O1 117.61(13) . . ? O2 S1 N1 113.19(13) . . ? O1 S1 N1 104.70(12) . . ? O2 S1 C1 106.48(13) . . ? O1 S1 C1 107.18(13) . . ? N1 S1 C1 107.14(13) . . ? C7 N1 S1 120.68(19) . . ? C11 N2 C7 124.6(2) . . ? C11 N2 H2 119(2) . . ? C7 N2 H2 116(2) . . ? C2 C1 C6 120.6(3) . . ? C2 C1 S1 120.3(2) . . ? C6 C1 S1 119.1(2) . . ? C5 C6 C1 119.9(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C4 C5 C6 118.1(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? F1 C4 C5 118.5(3) . . ? F1 C4 C3 118.1(3) . . ? C5 C4 C3 123.3(3) . . ? C4 C3 C2 118.4(3) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? N1 C7 N2 115.1(2) . . ? N1 C7 C8 128.5(3) . . ? N2 C7 C8 116.4(2) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 119.1(3) . . ? C11 C10 I1 121.1(2) . . ? C9 C10 I1 119.8(2) . . ? N2 C11 C10 119.2(3) . . ? N2 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.850(18) 2.047(19) 2.895(3) 176(3) 3_557 #----------------------------------------------------------------------------# data_A1_0.73(Br~CF3)0.27(Me~CF3) _database_code_depnum_ccdc_archive 'CCDC 871347' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.73(C12 H8 Br F3 N2 O2 S), 0.27(C12 H11 I N2 O2 S)' _chemical_formula_sum 'C12 H8.81 Br0.73 F2.19 I0.27 N2 O2 S' _chemical_formula_weight 379.29 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.365(4) _cell_length_b 19.488(3) _cell_length_c 5.6711(18) _cell_angle_alpha 90 _cell_angle_beta 99.63(3) _cell_angle_gamma 90 _cell_volume 1347.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2420 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.022 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.87 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 746 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.5158 _exptl_absorpt_correction_T_max 0.75 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.0456806 _diffrn_orient_matrix_ub_12 0.0075816 _diffrn_orient_matrix_ub_13 -0.0807328 _diffrn_orient_matrix_ub_21 -0.1713123 _diffrn_orient_matrix_ub_22 -0.0086584 _diffrn_orient_matrix_ub_23 0.0054374 _diffrn_orient_matrix_ub_31 -0.0227392 _diffrn_orient_matrix_ub_32 0.0499997 _diffrn_orient_matrix_ub_33 0.0131833 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.1187 _diffrn_reflns_av_unetI/netI 0.1144 _diffrn_reflns_number 6393 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _reflns_number_total 2290 _reflns_number_gt 1386 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0100P)^2^+10.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2290 _refine_ls_number_parameters 208 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1403 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.1797 _refine_ls_wR_factor_gt 0.1581 _refine_ls_goodness_of_fit_ref 0.95 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.459 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.098 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.17977(17) 0.11705(10) 1.1725(3) 0.0364(5) Uani 1 1 d . . . Br1 Br 0.56348(12) 0.12639(10) 0.5259(3) 0.0755(6) Uani 0.73 1 d PDU A 1 C14 C 0.5397(16) 0.1193(9) 0.578(3) 0.1 Uiso 0.27 1 d PD A 2 H14A H 0.5055 0.1201 0.4135 0.15 Uiso 0.27 1 calc PR A 2 H14B H 0.5834 0.0785 0.6093 0.15 Uiso 0.27 1 calc PR A 2 H14C H 0.5857 0.159 0.6127 0.15 Uiso 0.27 1 calc PR A 2 O1 O 0.2146(4) 0.0770(3) 1.3816(8) 0.0418(13) Uani 1 1 d . . . O2 O 0.1487(4) 0.1868(3) 1.2011(8) 0.0380(13) Uani 1 1 d . . . I1 I -0.2257(4) 0.1486(2) 0.1008(8) 0.0647(11) Uani 0.27 1 d P B 2 C12 C -0.2080(9) 0.1499(6) 0.196(2) 0.053(7) Uani 0.73 1 d PD B 1 F1 F -0.2890(6) 0.1019(3) 0.1388(12) 0.059(2) Uani 0.73 1 d PD B 1 F2 F -0.1616(7) 0.1651(4) 0.0019(12) 0.064(2) Uani 0.73 1 d PD B 1 F3 F -0.2675(5) 0.2072(3) 0.2357(10) 0.0478(16) Uani 0.73 1 d PD B 1 N1 N 0.0826(5) 0.0724(3) 1.0184(10) 0.0333(14) Uani 1 1 d . . . N2 N -0.0602(5) 0.0524(3) 0.7180(10) 0.0306(14) Uani 1 1 d D . . H2 H -0.065(6) 0.0130(15) 0.788(11) 0.07(3) Uiso 1 1 d D . . C1 C 0.2891(6) 0.1190(4) 1.0021(12) 0.0349(17) Uani 1 1 d D A . C6 C 0.3379(6) 0.0579(4) 0.9596(12) 0.044(2) Uani 1 1 d D . . H6 H 0.3163 0.0171 1.0231 0.052 Uiso 1 1 calc R . . C5 C 0.4200(7) 0.0581(5) 0.8206(13) 0.050(2) Uani 1 1 d D A . H5 H 0.4525 0.0171 0.7857 0.06 Uiso 1 1 calc R . . C4 C 0.4535(7) 0.1198(5) 0.7335(13) 0.047(2) Uani 1 1 d D . . C3 C 0.4059(7) 0.1802(5) 0.7873(15) 0.051(2) Uani 1 1 d D A . H3 H 0.4316 0.2217 0.7374 0.061 Uiso 1 1 calc R . . C2 C 0.3188(7) 0.1796(4) 0.9173(14) 0.042(2) Uani 1 1 d . . . H2A H 0.2825 0.22 0.9442 0.051 Uiso 1 1 calc R A . C7 C 0.0212(6) 0.0958(4) 0.8125(12) 0.0346(17) Uani 1 1 d D . . C8 C 0.0305(5) 0.1590(4) 0.7007(11) 0.0310(16) Uani 1 1 d D . . H8 H 0.0861 0.1896 0.7605 0.037 Uiso 1 1 calc R . . C9 C -0.0437(6) 0.1747(4) 0.5021(11) 0.0355(18) Uani 1 1 d D B . H9 H -0.0384 0.2167 0.4274 0.043 Uiso 1 1 calc R . . C11 C -0.1341(6) 0.0678(4) 0.5219(12) 0.0329(17) Uani 1 1 d D B . H11 H -0.1894 0.0369 0.4637 0.039 Uiso 1 1 calc R . . C10 C -0.1265(6) 0.1299(4) 0.4088(12) 0.0351(17) Uani 1 1 d 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 0.0482(11) 0.0229(10) 0.0358(9) 0.0021(8) 0.0002(8) -0.0030(9) Br1 0.0554(9) 0.0997(13) 0.0693(9) -0.0177(8) 0.0044(7) 0.0156(8) O1 0.056(3) 0.031(3) 0.034(3) 0.005(2) -0.005(2) -0.006(3) O2 0.050(3) 0.023(3) 0.039(3) -0.004(2) 0.003(2) -0.003(2) I1 0.068(2) 0.052(2) 0.066(2) 0.0046(15) -0.0108(19) 0.0069(17) C12 0.038(10) 0.032(8) 0.090(18) -0.002(10) 0.019(11) -0.001(7) F1 0.069(5) 0.020(3) 0.073(5) 0.010(3) -0.028(4) -0.019(3) F2 0.062(5) 0.093(6) 0.041(4) 0.022(4) 0.018(4) 0.004(4) F3 0.062(4) 0.036(4) 0.038(3) -0.007(3) -0.013(3) 0.019(3) N1 0.040(4) 0.022(3) 0.034(3) 0.002(3) -0.003(3) -0.007(3) N2 0.040(4) 0.014(3) 0.036(3) 0.004(3) 0.003(3) -0.001(3) C1 0.039(4) 0.024(4) 0.036(4) -0.002(3) -0.010(3) 0.003(3) C6 0.050(5) 0.028(4) 0.045(4) 0.003(4) -0.013(4) 0.000(4) C5 0.050(5) 0.047(6) 0.046(5) -0.014(4) -0.013(4) 0.017(4) C4 0.043(5) 0.046(5) 0.046(5) -0.013(4) -0.012(4) 0.004(4) C3 0.053(5) 0.044(5) 0.049(5) -0.001(4) -0.008(4) -0.008(5) C2 0.043(5) 0.029(4) 0.051(5) 0.003(4) -0.005(4) 0.002(4) C7 0.040(4) 0.031(4) 0.035(4) -0.002(3) 0.012(3) 0.000(3) C8 0.027(4) 0.026(4) 0.038(4) 0.002(3) 0.002(3) -0.005(3) C9 0.056(5) 0.023(4) 0.027(4) 0.008(3) 0.004(3) 0.002(4) C11 0.041(4) 0.023(4) 0.034(4) 0.003(3) 0.001(3) 0.003(3) C10 0.044(4) 0.031(4) 0.029(4) -0.008(3) 0.002(3) 0.001(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.425(5) . ? S1 O2 1.428(5) . ? S1 N1 1.617(6) . ? S1 C1 1.789(8) . ? Br1 C4 1.946(9) . ? C14 C4 1.49(2) . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? I1 C10 1.992(8) . ? C12 F2 1.356(12) . ? C12 F1 1.368(13) . ? C12 F3 1.377(12) . ? C12 C10 1.489(10) . ? N1 C7 1.361(9) . ? N2 C11 1.349(9) . ? N2 C7 1.355(9) . ? N2 H2 0.87(2) . ? C1 C2 1.349(11) . ? C1 C6 1.375(11) . ? C6 C5 1.385(12) . ? C6 H6 0.93 . ? C5 C4 1.389(13) . ? C5 H5 0.93 . ? C4 C3 1.373(12) . ? C3 C2 1.404(12) . ? C3 H3 0.93 . ? C2 H2A 0.93 . ? C7 C8 1.398(11) . ? C8 C9 1.363(10) . ? C8 H8 0.93 . ? C9 C10 1.382(10) . ? C9 H9 0.93 . ? C11 C10 1.381(10) . ? C11 H11 0.93 . ? 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 O1 S1 O2 118.4(3) . . ? O1 S1 N1 104.4(3) . . ? O2 S1 N1 112.6(3) . . ? O1 S1 C1 108.1(3) . . ? O2 S1 C1 106.4(3) . . ? N1 S1 C1 106.3(3) . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? F2 C12 F1 110.5(9) . . ? F2 C12 F3 105.4(9) . . ? F1 C12 F3 101.7(8) . . ? F2 C12 C10 113.2(8) . . ? F1 C12 C10 112.5(9) . . ? F3 C12 C10 112.7(8) . . ? C7 N1 S1 122.7(5) . . ? C11 N2 C7 122.9(6) . . ? C11 N2 H2 119(6) . . ? C7 N2 H2 119(6) . . ? C2 C1 C6 122.9(8) . . ? C2 C1 S1 119.1(6) . . ? C6 C1 S1 118.0(6) . . ? C1 C6 C5 118.8(8) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C5 C4 119.7(8) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C3 C4 C5 119.9(8) . . ? C3 C4 C14 120.8(9) . . ? C5 C4 C14 119.3(9) . . ? C3 C4 Br1 116.5(7) . . ? C5 C4 Br1 123.6(7) . . ? C14 C4 Br1 4.3(7) . . ? C4 C3 C2 120.4(9) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C1 C2 C3 118.2(8) . . ? C1 C2 H2A 120.9 . . ? C3 C2 H2A 120.9 . . ? N2 C7 N1 113.6(6) . . ? N2 C7 C8 118.8(7) . . ? N1 C7 C8 127.5(7) . . ? C9 C8 C7 118.5(7) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C10 121.9(7) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? N2 C11 C10 119.3(7) . . ? N2 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C10 C9 118.6(7) . . ? C11 C10 C12 121.1(8) . . ? C9 C10 C12 120.2(8) . . ? C11 C10 I1 119.2(6) . . ? C9 C10 I1 121.9(6) . . ? C12 C10 I1 7.2(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.87(2) 2.02(2) 2.892(8) 173(3) 3_557 #----------------------------------------------------------------------------# data_A1_H~I_alpha _database_code_depnum_ccdc_archive 'CCDC 871348' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H9 I N2 O2 S' _chemical_formula_sum 'C11 H9 I N2 O2 S' _chemical_formula_weight 360.16 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5231(5) _cell_length_b 19.2374(7) _cell_length_c 6.2008(2) _cell_angle_alpha 90 _cell_angle_beta 94.3530(10) _cell_angle_gamma 90 _cell_volume 1251.65(9) _cell_formula_units_Z 4 _cell_measurement_temperature 248(2) _cell_measurement_reflns_used 6398 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 26 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.911 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.716 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.4963 _exptl_absorpt_correction_T_max 0.923 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 248(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.1274 _diffrn_reflns_av_unetI/netI 0.1908 _diffrn_reflns_number 6841 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.977 _reflns_number_total 2163 _reflns_number_gt 1696 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0000P)^2^+5.0000P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.019(4) _refine_ls_number_reflns 2161 _refine_ls_number_parameters 159 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0791 _refine_ls_wR_factor_ref 0.1930 _refine_ls_wR_factor_gt 0.1831 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.736 _refine_diff_density_min -1.186 _refine_diff_density_rms 0.184 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.22123(19) 0.11935(12) 1.1356(3) 0.0480(6) Uani 1 1 d . . . I1 I -0.23511(6) 0.14498(4) 0.18207(9) 0.0652(4) Uani 1 1 d . . . O1 O 0.2617(6) 0.0774(4) 1.3210(9) 0.0673(18) Uani 1 1 d . . . O2 O 0.1815(6) 0.1894(3) 1.1686(10) 0.0660(17) Uani 1 1 d . . . N1 N 0.1063(6) 0.0756(4) 1.0130(12) 0.0541(17) Uani 1 1 d D . . H1 H 0.087(9) 0.040(3) 1.094(14) 0.07(3) Uiso 1 1 d D . . N2 N -0.0507(6) 0.0505(4) 0.7517(11) 0.0492(16) Uani 1 1 d . . . C1 C 0.3445(7) 0.1219(5) 0.9565(12) 0.0503(19) Uani 1 1 d . . . C2 C 0.3957(9) 0.1842(7) 0.9050(18) 0.078(3) Uani 1 1 d . . . H2 H 0.3624 0.2261 0.9544 0.093 Uiso 1 1 calc R . . C3 C 0.4978(11) 0.1839(10) 0.778(2) 0.109(6) Uani 1 1 d . . . H3 H 0.537 0.2262 0.7462 0.13 Uiso 1 1 calc R . . C4 C 0.5426(14) 0.1241(13) 0.699(2) 0.122(7) Uani 1 1 d . . . H4 H 0.6108 0.1246 0.61 0.146 Uiso 1 1 calc R . . C5 C 0.4878(14) 0.0634(12) 0.751(2) 0.117(6) Uani 1 1 d . . . H5 H 0.5201 0.0218 0.6972 0.14 Uiso 1 1 calc R . . C6 C 0.3883(9) 0.0598(7) 0.8770(16) 0.073(3) Uani 1 1 d . . . H6 H 0.3507 0.017 0.909 0.087 Uiso 1 1 calc R . . C7 C 0.0355(7) 0.0949(4) 0.8230(12) 0.0433(17) Uani 1 1 d . . . C8 C 0.0525(8) 0.1597(5) 0.7165(15) 0.052(2) Uani 1 1 d . . . H8 H 0.1131 0.1922 0.772 0.063 Uiso 1 1 calc R . . C9 C -0.0211(8) 0.1725(5) 0.5343(12) 0.0507(19) Uani 1 1 d . . . H9 H -0.0102 0.2138 0.4571 0.061 Uiso 1 1 calc R . . C10 C -0.1117(7) 0.1256(5) 0.4613(12) 0.0450(17) Uani 1 1 d . . . C11 C -0.1255(7) 0.0641(5) 0.5692(12) 0.0493(18) Uani 1 1 d . . . H11 H -0.1867 0.0315 0.5166 0.059 Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0453(11) 0.0504(12) 0.0487(11) -0.0019(9) 0.0059(8) -0.0014(9) I1 0.0591(5) 0.0844(7) 0.0517(5) 0.0103(3) 0.0005(3) 0.0076(3) O1 0.060(4) 0.089(5) 0.051(3) 0.014(3) -0.004(3) -0.011(3) O2 0.074(4) 0.055(4) 0.071(4) -0.015(3) 0.015(3) 0.009(3) N1 0.046(4) 0.053(4) 0.061(4) 0.015(3) -0.010(3) -0.007(3) N2 0.037(3) 0.058(4) 0.053(4) 0.001(3) 0.009(3) -0.002(3) C1 0.028(4) 0.079(6) 0.044(4) -0.001(4) -0.002(3) -0.004(4) C2 0.043(5) 0.093(9) 0.096(7) 0.033(7) -0.001(5) -0.014(5) C3 0.050(6) 0.163(16) 0.112(10) 0.068(11) 0.003(6) -0.023(8) C4 0.065(8) 0.23(2) 0.067(8) 0.040(11) 0.008(6) 0.055(11) C5 0.093(10) 0.21(2) 0.052(6) -0.015(9) -0.003(6) 0.067(11) C6 0.051(5) 0.095(8) 0.072(6) -0.021(6) -0.001(4) 0.014(5) C7 0.032(3) 0.051(5) 0.047(4) 0.004(3) 0.007(3) 0.002(3) C8 0.049(4) 0.047(5) 0.062(5) 0.005(4) 0.011(4) 0.003(4) C9 0.057(5) 0.050(5) 0.048(4) 0.005(4) 0.019(4) 0.004(4) C10 0.037(4) 0.060(5) 0.038(4) 0.009(3) 0.005(3) 0.011(3) C11 0.045(4) 0.053(5) 0.050(4) -0.001(4) 0.005(3) -0.002(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2 1.429(7) . ? S1 O1 1.442(7) . ? S1 N1 1.615(7) . ? S1 C1 1.771(7) . ? I1 C10 2.117(8) . ? N1 C7 1.396(10) . ? N1 H1 0.88(2) . ? N2 C7 1.300(11) . ? N2 C11 1.354(10) . ? C1 C2 1.361(15) . ? C1 C6 1.385(14) . ? C2 C3 1.379(17) . ? C2 H2 0.94 . ? C3 C4 1.35(3) . ? C3 H3 0.94 . ? C4 C5 1.35(3) . ? C4 H4 0.94 . ? C5 C6 1.355(18) . ? C5 H5 0.94 . ? C6 H6 0.94 . ? C7 C8 1.428(12) . ? C8 C9 1.343(13) . ? C8 H8 0.94 . ? C9 C10 1.365(13) . ? C9 H9 0.94 . ? C10 C11 1.372(12) . ? C11 H11 0.94 . ? 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 O2 S1 O1 119.0(4) . . ? O2 S1 N1 110.0(4) . . ? O1 S1 N1 104.4(4) . . ? O2 S1 C1 107.4(4) . . ? O1 S1 C1 109.2(4) . . ? N1 S1 C1 106.1(4) . . ? C7 N1 S1 126.2(6) . . ? C7 N1 H1 124(7) . . ? S1 N1 H1 109(7) . . ? C7 N2 C11 120.2(7) . . ? C2 C1 C6 121.9(9) . . ? C2 C1 S1 119.5(8) . . ? C6 C1 S1 118.6(8) . . ? C1 C2 C3 118.0(13) . . ? C1 C2 H2 121 . . ? C3 C2 H2 121 . . ? C4 C3 C2 121.3(15) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.9(13) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 122.9(16) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C5 C6 C1 116.9(14) . . ? C5 C6 H6 121.5 . . ? C1 C6 H6 121.5 . . ? N2 C7 N1 115.2(7) . . ? N2 C7 C8 121.7(8) . . ? N1 C7 C8 123.1(7) . . ? C9 C8 C7 117.7(9) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C8 C9 C10 120.1(8) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? C9 C10 C11 120.3(7) . . ? C9 C10 I1 121.6(6) . . ? C11 C10 I1 118.0(6) . . ? N2 C11 C10 119.9(8) . . ? N2 C11 H11 120 . . ? C10 C11 H11 120 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N2 0.88(2) 2.04(3) 2.912(10) 172(10) 3_557 #----------------------------------------------------------------------------# data_A1_CF3~CF3 _database_code_depnum_ccdc_archive 'CCDC 871349' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H8 F6 N2 O2 S' _chemical_formula_sum 'C13 H8 F6 N2 O2 S' _chemical_formula_weight 370.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.4694(6) _cell_length_b 19.4348(9) _cell_length_c 5.77090(10) _cell_angle_alpha 90 _cell_angle_beta 99.010(3) _cell_angle_gamma 90 _cell_volume 1381.26(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11688 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.9145 _exptl_absorpt_correction_T_max 0.975 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_number 14959 _diffrn_reflns_av_R_equivalents 0.1173 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2469 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.992 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0751P)^2^+1.2751P] 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_number_reflns 2468 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1254 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.296 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.078 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.17191(5) 0.11856(3) 1.16314(12) 0.0209(2) Uani 1 1 d . . . O1 O 0.20743(16) 0.07918(10) 1.3720(3) 0.0274(5) Uani 1 1 d . . . O2 O 0.13987(16) 0.18903(9) 1.1901(3) 0.0254(5) Uani 1 1 d . . . N1 N 0.07754(18) 0.07234(11) 1.0156(4) 0.0220(5) Uani 1 1 d . . . N2 N -0.06231(18) 0.05284(11) 0.7205(4) 0.0208(5) Uani 1 1 d D . . H2 H -0.066(2) 0.0128(11) 0.791(5) 0.025 Uiso 1 1 d D . . C1 C 0.2801(2) 0.11949(13) 0.9963(5) 0.0208(6) Uani 1 1 d . . . C2 C 0.3160(2) 0.18154(14) 0.9167(5) 0.0242(6) Uani 1 1 d . . . H2A H 0.2812 0.2235 0.9454 0.029 Uiso 1 1 calc R . . C3 C 0.4031(2) 0.18127(15) 0.7948(5) 0.0265(6) Uani 1 1 d . . . H3 H 0.4305 0.2234 0.7445 0.032 Uiso 1 1 calc R . . C4 C 0.4505(2) 0.11956(14) 0.7463(5) 0.0249(6) Uani 1 1 d . . . C5 C 0.4125(2) 0.05743(15) 0.8229(5) 0.0281(7) Uani 1 1 d . . . H5 H 0.4447 0.0152 0.7874 0.034 Uiso 1 1 calc R . . C6 C 0.3278(2) 0.05783(14) 0.9505(5) 0.0249(6) Uani 1 1 d . . . H6 H 0.3023 0.0159 1.0067 0.03 Uiso 1 1 calc R . . C7 C 0.0176(2) 0.09634(13) 0.8186(5) 0.0205(6) Uani 1 1 d . . . C8 C 0.0260(2) 0.15974(14) 0.6996(5) 0.0220(6) Uani 1 1 d . . . H8 H 0.083 0.1909 0.755 0.026 Uiso 1 1 calc R . . C9 C -0.0469(2) 0.17596(14) 0.5075(5) 0.0216(6) Uani 1 1 d . . . H9 H -0.0413 0.2188 0.4312 0.026 Uiso 1 1 calc R . . C10 C -0.1309(2) 0.13000(14) 0.4198(5) 0.0224(6) Uani 1 1 d . . . C11 C -0.1360(2) 0.06814(14) 0.5294(5) 0.0218(6) Uani 1 1 d . . . H11 H -0.1912 0.036 0.4719 0.026 Uiso 1 1 calc R . . C12 C 0.5406(2) 0.11996(16) 0.6038(5) 0.0309(7) Uani 1 1 d . . . C13 C -0.2119(2) 0.14922(14) 0.2125(5) 0.0246(6) Uani 1 1 d . . . F1 F -0.29142(15) 0.10351(9) 0.1641(3) 0.0437(5) Uani 1 1 d . . . F2 F -0.16627(15) 0.15669(12) 0.0184(3) 0.0481(6) Uani 1 1 d . . . F3 F -0.25945(15) 0.20922(9) 0.2411(3) 0.0411(5) Uani 1 1 d . . . F4 F 0.61017(16) 0.17124(11) 0.6609(4) 0.0535(6) Uani 1 1 d . . . F5 F 0.60036(17) 0.06255(11) 0.6269(4) 0.0527(6) Uani 1 1 d . . . F6 F 0.50343(16) 0.12597(14) 0.3762(3) 0.0618(7) 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 0.0241(4) 0.0166(4) 0.0219(4) 0.0004(2) 0.0033(3) -0.0018(3) O1 0.0334(11) 0.0244(11) 0.0231(11) 0.0037(8) 0.0008(8) -0.0027(9) O2 0.0303(11) 0.0200(10) 0.0275(11) -0.0024(8) 0.0096(8) 0.0006(8) N1 0.0224(12) 0.0180(12) 0.0245(12) 0.0017(9) 0.0005(9) -0.0019(9) N2 0.0237(12) 0.0154(12) 0.0229(12) 0.0025(9) 0.0028(9) -0.0013(10) C1 0.0172(14) 0.0204(14) 0.0231(15) -0.0003(10) -0.0022(11) -0.0017(11) C2 0.0241(15) 0.0195(14) 0.0289(15) 0.0002(11) 0.0035(11) -0.0011(11) C3 0.0253(15) 0.0236(15) 0.0295(16) 0.0041(11) 0.0009(12) -0.0038(12) C4 0.0215(15) 0.0303(16) 0.0217(15) -0.0020(11) 0.0001(11) 0.0000(12) C5 0.0280(16) 0.0265(16) 0.0285(16) -0.0050(12) 0.0005(12) 0.0050(12) C6 0.0280(15) 0.0210(14) 0.0249(15) 0.0005(11) 0.0015(12) -0.0009(12) C7 0.0198(14) 0.0182(14) 0.0250(15) -0.0008(11) 0.0083(11) 0.0014(11) C8 0.0232(14) 0.0192(14) 0.0247(14) 0.0001(10) 0.0067(11) -0.0038(11) C9 0.0247(14) 0.0195(14) 0.0226(14) 0.0021(10) 0.0097(11) 0.0001(11) C10 0.0248(15) 0.0222(15) 0.0220(14) -0.0005(11) 0.0089(11) 0.0026(11) C11 0.0233(14) 0.0211(14) 0.0212(14) 0.0004(10) 0.0046(11) -0.0004(11) C12 0.0272(17) 0.0373(18) 0.0274(17) -0.0010(12) 0.0017(12) 0.0020(13) C13 0.0276(15) 0.0214(15) 0.0255(15) 0.0012(11) 0.0066(11) 0.0017(12) F1 0.0420(11) 0.0340(11) 0.0479(12) 0.0100(8) -0.0149(9) -0.0126(8) F2 0.0380(11) 0.0829(16) 0.0253(10) 0.0121(9) 0.0105(8) 0.0171(10) F3 0.0489(12) 0.0324(10) 0.0379(11) -0.0027(8) -0.0061(8) 0.0177(8) F4 0.0391(12) 0.0596(14) 0.0675(14) -0.0165(11) 0.0265(10) -0.0186(10) F5 0.0448(12) 0.0545(13) 0.0647(14) 0.0067(10) 0.0269(10) 0.0168(10) F6 0.0360(12) 0.125(2) 0.0245(11) 0.0046(11) 0.0056(8) 0.0079(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.4380(19) . ? S1 O2 1.442(2) . ? S1 N1 1.613(2) . ? S1 C1 1.776(3) . ? N1 C7 1.343(3) . ? N2 C11 1.353(3) . ? N2 C7 1.361(3) . ? N2 H2 0.882(17) . ? C1 C6 1.381(4) . ? C1 C2 1.389(4) . ? C2 C3 1.384(4) . ? C2 H2A 0.95 . ? C3 C4 1.385(4) . ? C3 H3 0.95 . ? C4 C5 1.394(4) . ? C4 C12 1.492(4) . ? C5 C6 1.379(4) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.422(4) . ? C8 C9 1.356(4) . ? C8 H8 0.95 . ? C9 C10 1.409(4) . ? C9 H9 0.95 . ? C10 C11 1.365(4) . ? C10 C13 1.487(4) . ? C11 H11 0.95 . ? C12 F6 1.327(4) . ? C12 F4 1.329(4) . ? C12 F5 1.337(4) . ? C13 F1 1.328(3) . ? C13 F3 1.330(3) . ? C13 F2 1.341(3) . ? 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 O1 S1 O2 117.98(12) . . ? O1 S1 N1 104.46(12) . . ? O2 S1 N1 113.22(12) . . ? O1 S1 C1 107.43(12) . . ? O2 S1 C1 107.20(12) . . ? N1 S1 C1 105.83(12) . . ? C7 N1 S1 121.11(19) . . ? C11 N2 C7 124.2(2) . . ? C11 N2 H2 119.4(19) . . ? C7 N2 H2 116.4(19) . . ? C6 C1 C2 121.3(3) . . ? C6 C1 S1 118.8(2) . . ? C2 C1 S1 120.0(2) . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 C12 119.2(3) . . ? C5 C4 C12 120.1(3) . . ? C6 C5 C4 119.4(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 N2 114.2(2) . . ? N1 C7 C8 129.5(2) . . ? N2 C7 C8 116.2(2) . . ? C9 C8 C7 120.4(3) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.6(3) . . ? C11 C10 C13 121.2(3) . . ? C9 C10 C13 120.2(2) . . ? N2 C11 C10 119.7(3) . . ? N2 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? F6 C12 F4 107.0(3) . . ? F6 C12 F5 106.0(3) . . ? F4 C12 F5 105.6(2) . . ? F6 C12 C4 111.7(3) . . ? F4 C12 C4 112.7(2) . . ? F5 C12 C4 113.4(3) . . ? F1 C13 F3 106.2(2) . . ? F1 C13 F2 107.3(2) . . ? F3 C13 F2 105.3(2) . . ? F1 C13 C10 113.1(2) . . ? F3 C13 C10 112.4(2) . . ? F2 C13 C10 112.0(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.882(17) 2.015(18) 2.892(3) 173(3) 3_557 #----------------------------------------------------------------------------# data_A1_I~CF3_alpha _database_code_depnum_ccdc_archive 'CCDC 871350' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety ; 0.96(C12 H8 F3 I N2 O2 S), 0.04(C11 H8 I2 N2 O2 S) ; _chemical_formula_sum 'C11.96 H8 F2.88 I1.04 N2 O2 S' _chemical_formula_weight 430.48 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7889(4) _cell_length_b 19.4009(8) _cell_length_c 5.7270(2) _cell_angle_alpha 90 _cell_angle_beta 100.650(2) _cell_angle_gamma 90 _cell_volume 1396.48(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6686 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 26 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 827 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.6276 _exptl_absorpt_correction_T_max 0.8823 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_unetI/netI 0.0424 _diffrn_reflns_number 12632 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.97 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 2705 _reflns_number_gt 2122 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0592P)^2^+1.1454P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0016(4) _refine_ls_number_reflns 2705 _refine_ls_number_parameters 200 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.652 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.101 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.17300(7) 0.11652(4) 1.17771(16) 0.0204(2) Uani 1 1 d . . . I1 I 0.55443(2) 0.121125(16) 0.54191(5) 0.04063(15) Uani 1 1 d . . . O1 O 0.2068(2) 0.07566(13) 1.3881(5) 0.0279(6) Uani 1 1 d . . . O2 O 0.1422(2) 0.18698(12) 1.2066(5) 0.0242(6) Uani 1 1 d . . . F1 F -0.2840(2) 0.10611(13) 0.1478(5) 0.0443(7) Uani 0.96 1 d P A 1 F2 F -0.1615(2) 0.15854(16) 0.0041(4) 0.0454(7) Uani 0.96 1 d P A 1 F3 F -0.2504(2) 0.21161(13) 0.2254(5) 0.0409(6) Uani 0.96 1 d P A 1 N1 N 0.0795(2) 0.07109(14) 1.0217(5) 0.0208(6) Uani 1 1 d . . . N2 N -0.0589(2) 0.05312(15) 0.7169(5) 0.0204(6) Uani 1 1 d D . . H2 H -0.065(3) 0.0164(17) 0.802(7) 0.042(13) Uiso 1 1 d D . . C1 C 0.2782(3) 0.11797(18) 1.0168(7) 0.0208(7) Uani 1 1 d . . . C6 C 0.3272(3) 0.05656(18) 0.9729(7) 0.0266(8) Uani 1 1 d . . . H6 H 0.3062 0.0145 1.0354 0.032 Uiso 1 1 calc R . . C5 C 0.4064(3) 0.0566(2) 0.8388(7) 0.0306(9) Uani 1 1 d . . . H5 H 0.439 0.0148 0.8042 0.037 Uiso 1 1 calc R . . C4 C 0.4377(3) 0.1194(2) 0.7549(7) 0.0267(8) Uani 1 1 d . . . C3 C 0.3918(3) 0.18096(19) 0.8034(7) 0.0254(8) Uani 1 1 d . . . H3 H 0.4165 0.2234 0.7509 0.03 Uiso 1 1 calc R . . C2 C 0.3097(3) 0.17998(18) 0.9292(7) 0.0235(8) Uani 1 1 d . . . H2A H 0.2746 0.2216 0.956 0.028 Uiso 1 1 calc R . . C7 C 0.0208(3) 0.09625(17) 0.8206(6) 0.0188(7) Uani 1 1 d . . . C8 C 0.0299(3) 0.15986(17) 0.7034(6) 0.0191(7) Uani 1 1 d . . . H8 H 0.0863 0.1907 0.7626 0.023 Uiso 1 1 calc R . . C9 C -0.0425(3) 0.17652(18) 0.5055(6) 0.0219(8) Uani 1 1 d D . . H9 H -0.038 0.2201 0.4323 0.026 Uiso 1 1 calc R . . C11 C -0.1306(3) 0.06880(18) 0.5233(6) 0.0212(8) Uani 1 1 d D . . H11 H -0.1864 0.0374 0.4653 0.025 Uiso 1 1 calc R . . C10 C -0.1237(3) 0.13039(17) 0.4079(6) 0.0211(7) Uani 1 1 d D . . C12 C -0.2048(4) 0.1508(2) 0.1963(9) 0.0233(9) Uani 0.96 1 d PD A 1 I2 I -0.2297(6) 0.1511(4) 0.0999(12) 0.030(2) Uiso 0.04 1 d PD A 2 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 0.0229(5) 0.0155(4) 0.0225(5) 0.0004(3) 0.0038(4) -0.0027(3) I1 0.02750(19) 0.0606(2) 0.0355(2) -0.00658(13) 0.01031(12) 0.00397(13) O1 0.0333(15) 0.0238(13) 0.0245(14) 0.0052(11) -0.0003(11) -0.0050(11) O2 0.0289(14) 0.0178(13) 0.0275(14) -0.0021(10) 0.0093(11) -0.0022(11) F1 0.0459(16) 0.0355(14) 0.0428(16) 0.0110(11) -0.0144(13) -0.0145(12) F2 0.0405(15) 0.075(2) 0.0231(13) 0.0131(13) 0.0112(11) 0.0161(14) F3 0.0464(15) 0.0345(14) 0.0379(15) -0.0026(11) -0.0029(12) 0.0172(12) N1 0.0188(14) 0.0149(14) 0.0275(17) 0.0017(12) 0.0012(12) -0.0041(12) N2 0.0224(15) 0.0152(15) 0.0234(16) 0.0039(12) 0.0037(13) -0.0008(12) C1 0.0170(17) 0.0209(17) 0.0236(19) -0.0023(14) 0.0011(14) -0.0005(14) C6 0.031(2) 0.0157(18) 0.031(2) -0.0018(15) -0.0014(16) 0.0003(15) C5 0.031(2) 0.028(2) 0.031(2) -0.0054(16) 0.0018(17) 0.0083(17) C4 0.0178(18) 0.039(2) 0.023(2) -0.0043(16) 0.0020(15) 0.0004(16) C3 0.0201(18) 0.0240(19) 0.032(2) 0.0036(16) 0.0061(15) -0.0015(15) C2 0.0218(18) 0.0171(18) 0.031(2) 0.0021(15) 0.0034(15) 0.0020(15) C7 0.0203(18) 0.0140(16) 0.0237(19) -0.0005(14) 0.0083(15) 0.0011(14) C8 0.0188(17) 0.0179(18) 0.0225(19) -0.0011(14) 0.0089(14) -0.0013(14) C9 0.0239(19) 0.0171(17) 0.028(2) 0.0020(14) 0.0127(15) 0.0022(14) C11 0.0213(18) 0.0199(17) 0.0232(19) 0.0000(14) 0.0060(15) -0.0003(15) C10 0.0256(19) 0.0193(17) 0.0194(18) 0.0016(14) 0.0066(14) 0.0024(15) C12 0.025(2) 0.015(2) 0.033(3) 0.0054(18) 0.012(2) 0.0046(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.440(3) . ? S1 O2 1.441(3) . ? S1 N1 1.616(3) . ? S1 C1 1.766(4) . ? I1 C4 2.096(4) . ? F1 C12 1.323(5) . ? F2 C12 1.328(5) . ? F3 C12 1.340(5) . ? N1 C7 1.344(5) . ? N2 C11 1.337(5) . ? N2 C7 1.367(5) . ? N2 H2 0.88(2) . ? C1 C6 1.391(5) . ? C1 C2 1.391(5) . ? C6 C5 1.380(6) . ? C6 H6 0.95 . ? C5 C4 1.394(6) . ? C5 H5 0.95 . ? C4 C3 1.381(5) . ? C3 C2 1.379(5) . ? C3 H3 0.95 . ? C2 H2A 0.95 . ? C7 C8 1.420(5) . ? C8 C9 1.363(5) . ? C8 H8 0.95 . ? C9 C10 1.406(5) . ? C9 H9 0.95 . ? C11 C10 1.376(5) . ? C11 H11 0.95 . ? C10 C12 1.495(5) . ? C10 I2 2.056(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 O1 S1 O2 118.19(16) . . ? O1 S1 N1 103.85(15) . . ? O2 S1 N1 113.01(16) . . ? O1 S1 C1 107.77(17) . . ? O2 S1 C1 107.20(16) . . ? N1 S1 C1 106.14(16) . . ? C7 N1 S1 120.9(2) . . ? C11 N2 C7 124.3(3) . . ? C11 N2 H2 122(3) . . ? C7 N2 H2 113(3) . . ? C6 C1 C2 120.4(4) . . ? C6 C1 S1 119.5(3) . . ? C2 C1 S1 120.0(3) . . ? C5 C6 C1 120.1(4) . . ? C5 C6 H6 120 . . ? C1 C6 H6 120 . . ? C6 C5 C4 118.6(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C3 C4 C5 121.8(4) . . ? C3 C4 I1 118.5(3) . . ? C5 C4 I1 119.6(3) . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C2 C1 119.9(3) . . ? C3 C2 H2A 120 . . ? C1 C2 H2A 120 . . ? N1 C7 N2 113.8(3) . . ? N1 C7 C8 129.7(3) . . ? N2 C7 C8 116.5(3) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.2(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? N2 C11 C10 120.0(3) . . ? N2 C11 H11 120 . . ? C10 C11 H11 120 . . ? C11 C10 C9 118.0(3) . . ? C11 C10 C12 121.5(3) . . ? C9 C10 C12 120.3(3) . . ? C11 C10 I2 119.4(3) . . ? C9 C10 I2 122.6(3) . . ? C12 C10 I2 5.4(3) . . ? F1 C12 F2 108.6(4) . . ? F1 C12 F3 105.6(3) . . ? F2 C12 F3 105.1(3) . . ? F1 C12 C10 112.7(3) . . ? F2 C12 C10 111.6(3) . . ? F3 C12 C10 112.7(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.88(2) 2.00(2) 2.874(4) 176(5) 3_557 #----------------------------------------------------------------------------# data_A1_Br~CF3_alpha _database_code_depnum_ccdc_archive 'CCDC 871351' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 Br F3 N2 O2 S' _chemical_formula_sum 'C12 H8 Br F3 N2 O2 S' _chemical_formula_weight 381.17 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3877(6) _cell_length_b 19.4324(9) _cell_length_c 5.7076(2) _cell_angle_alpha 90 _cell_angle_beta 100.458(2) _cell_angle_gamma 90 _cell_volume 1351.13(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5839 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.874 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.295 _exptl_absorpt_correction_T_max 0.726 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_unetI/netI 0.0441 _diffrn_reflns_number 10307 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 2611 _reflns_number_gt 2035 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0635P)^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 SHELXL _refine_ls_extinction_coef 0.0055(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2611 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.940 _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 0.17740(6) 0.11670(3) 1.17364(11) 0.01859(18) Uani 1 1 d . . . Br1 Br 0.55681(3) 0.117770(19) 0.54702(6) 0.04309(16) Uani 1 1 d . . . O1 O 0.21266(16) 0.07623(9) 1.3852(3) 0.0264(4) Uani 1 1 d . . . O2 O 0.14595(15) 0.18716(8) 1.2032(3) 0.0225(4) Uani 1 1 d . . . F1 F -0.29510(15) 0.10573(8) 0.1423(3) 0.0361(4) Uani 1 1 d . . . F2 F -0.16877(15) 0.15953(10) 0.0021(3) 0.0400(5) Uani 1 1 d . . . F3 F -0.26188(15) 0.21170(8) 0.2260(3) 0.0366(4) Uani 1 1 d . . . N1 N 0.08096(18) 0.07167(10) 1.0190(4) 0.0196(5) Uani 1 1 d . . . N2 N -0.06276(18) 0.05351(10) 0.7145(4) 0.0181(5) Uani 1 1 d D . . H2 H -0.071(2) 0.0144(11) 0.783(5) 0.031(8) Uiso 1 1 d D . . C1 C 0.2856(2) 0.11776(12) 1.0091(4) 0.0196(6) Uani 1 1 d . . . C6 C 0.3339(2) 0.05609(13) 0.9618(5) 0.0237(6) Uani 1 1 d . . . H6 H 0.3113 0.0142 1.0241 0.028 Uiso 1 1 calc R . . C5 C 0.4147(2) 0.05548(15) 0.8247(5) 0.0288(6) Uani 1 1 d . . . H5 H 0.4463 0.0133 0.7863 0.035 Uiso 1 1 calc R . . C4 C 0.4490(2) 0.11791(14) 0.7436(5) 0.0279(6) Uani 1 1 d . . . C3 C 0.4037(2) 0.17955(15) 0.7939(5) 0.0278(6) Uani 1 1 d . . . H3 H 0.4297 0.2216 0.7399 0.033 Uiso 1 1 calc R . . C2 C 0.3196(2) 0.17961(13) 0.9245(5) 0.0237(6) Uani 1 1 d . . . H2A H 0.2856 0.2216 0.9559 0.028 Uiso 1 1 calc R . . C7 C 0.0197(2) 0.09630(12) 0.8181(4) 0.0182(5) Uani 1 1 d . . . C8 C 0.0290(2) 0.16014(12) 0.6995(4) 0.0175(5) Uani 1 1 d . . . H8 H 0.0871 0.1910 0.7586 0.021 Uiso 1 1 calc R . . C9 C -0.0453(2) 0.17661(12) 0.5021(4) 0.0198(6) Uani 1 1 d . . . H9 H -0.0392 0.2194 0.4250 0.024 Uiso 1 1 calc R . . C11 C -0.1371(2) 0.06935(12) 0.5197(4) 0.0204(6) Uani 1 1 d . . . H11 H -0.1934 0.0375 0.4587 0.024 Uiso 1 1 calc R . . C10 C -0.1313(2) 0.13140(12) 0.4097(5) 0.0190(6) Uani 1 1 d . . . C12 C -0.2140(2) 0.15166(13) 0.1969(4) 0.0217(6) 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 0.0232(4) 0.0138(3) 0.0188(3) 0.0003(2) 0.0040(3) -0.0026(2) Br1 0.0314(2) 0.0658(3) 0.0354(2) -0.00465(15) 0.01490(15) 0.00354(15) O1 0.0328(12) 0.0226(9) 0.0213(9) 0.0043(8) -0.0017(8) -0.0044(8) O2 0.0291(11) 0.0150(9) 0.0251(9) -0.0019(7) 0.0091(8) 0.0001(7) F1 0.0402(11) 0.0291(8) 0.0335(9) 0.0079(7) -0.0082(8) -0.0098(8) F2 0.0429(11) 0.0608(12) 0.0191(8) 0.0118(8) 0.0126(7) 0.0134(9) F3 0.0466(11) 0.0264(8) 0.0329(9) -0.0034(7) -0.0030(8) 0.0161(8) N1 0.0223(12) 0.0149(10) 0.0204(10) 0.0027(9) 0.0006(9) -0.0044(9) N2 0.0222(12) 0.0133(10) 0.0188(10) 0.0042(9) 0.0037(9) -0.0028(8) C1 0.0191(15) 0.0208(13) 0.0179(12) -0.0018(10) 0.0005(11) 0.0007(10) C6 0.0268(16) 0.0168(12) 0.0253(13) -0.0007(11) -0.0013(12) 0.0030(11) C5 0.0309(17) 0.0288(14) 0.0254(14) -0.0083(12) 0.0015(12) 0.0086(12) C4 0.0210(16) 0.0382(17) 0.0235(14) -0.0012(12) 0.0013(12) 0.0016(12) C3 0.0229(16) 0.0290(15) 0.0312(15) 0.0064(12) 0.0037(12) -0.0022(11) C2 0.0248(15) 0.0164(12) 0.0303(14) 0.0031(11) 0.0062(12) -0.0009(10) C7 0.0223(15) 0.0151(12) 0.0188(12) -0.0006(10) 0.0076(11) 0.0006(10) C8 0.0193(14) 0.0134(11) 0.0210(12) -0.0003(10) 0.0067(11) -0.0005(10) C9 0.0250(15) 0.0159(12) 0.0210(13) 0.0028(10) 0.0106(11) -0.0002(10) C11 0.0256(15) 0.0151(12) 0.0211(13) -0.0019(10) 0.0060(11) -0.0018(10) C10 0.0265(15) 0.0147(11) 0.0182(12) 0.0010(10) 0.0100(11) 0.0027(10) C12 0.0261(15) 0.0199(12) 0.0207(13) 0.0023(11) 0.0083(11) 0.0028(11) _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 O1 1.4408(19) . ? S1 O2 1.4417(17) . ? S1 N1 1.609(2) . ? S1 C1 1.771(3) . ? Br1 C4 1.894(3) . ? F1 C12 1.338(3) . ? F2 C12 1.342(3) . ? F3 C12 1.333(3) . ? N1 C7 1.343(3) . ? N2 C11 1.344(3) . ? N2 C7 1.365(3) . ? N2 H2 0.868(17) . ? C1 C6 1.388(4) . ? C1 C2 1.389(4) . ? C6 C5 1.377(4) . ? C6 H6 0.9500 . ? C5 C4 1.392(4) . ? C5 H5 0.9500 . ? C4 C3 1.375(4) . ? C3 C2 1.386(4) . ? C3 H3 0.9500 . ? C2 H2A 0.9500 . ? C7 C8 1.428(3) . ? C8 C9 1.358(4) . ? C8 H8 0.9500 . ? C9 C10 1.407(4) . ? C9 H9 0.9500 . ? C11 C10 1.367(3) . ? C11 H11 0.9500 . ? C10 C12 1.493(4) . ? 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 O1 S1 O2 117.88(11) . . ? O1 S1 N1 104.17(11) . . ? O2 S1 N1 113.03(11) . . ? O1 S1 C1 107.90(12) . . ? O2 S1 C1 107.31(11) . . ? N1 S1 C1 105.86(12) . . ? C7 N1 S1 121.52(17) . . ? C11 N2 C7 124.4(2) . . ? C11 N2 H2 117(2) . . ? C7 N2 H2 119(2) . . ? C6 C1 C2 120.7(3) . . ? C6 C1 S1 119.2(2) . . ? C2 C1 S1 120.1(2) . . ? C5 C6 C1 120.1(3) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C6 C5 C4 118.6(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C3 C4 C5 121.9(3) . . ? C3 C4 Br1 118.9(2) . . ? C5 C4 Br1 119.1(2) . . ? C4 C3 C2 119.2(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C2 C1 119.4(2) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? N1 C7 N2 114.5(2) . . ? N1 C7 C8 129.2(2) . . ? N2 C7 C8 116.3(2) . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.1(2) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? N2 C11 C10 119.8(2) . . ? N2 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C10 C9 118.5(3) . . ? C11 C10 C12 121.4(2) . . ? C9 C10 C12 120.1(2) . . ? F3 C12 F1 106.3(2) . . ? F3 C12 F2 105.4(2) . . ? F1 C12 F2 107.0(2) . . ? F3 C12 C10 112.6(2) . . ? F1 C12 C10 112.9(2) . . ? F2 C12 C10 112.1(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.868(17) 2.037(18) 2.900(3) 173(3) 3_557 _refine_diff_density_max 0.430 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# data_A1_Cl~CF3 _database_code_depnum_ccdc_archive 'CCDC 871352' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 Cl F3 N2 O2 S' _chemical_formula_sum 'C12 H8 Cl F3 N2 O2 S' _chemical_formula_weight 336.71 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1508(7) _cell_length_b 19.4666(11) _cell_length_c 5.6756(2) _cell_angle_alpha 90 _cell_angle_beta 99.863(3) _cell_angle_gamma 90 _cell_volume 1322.64(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8204 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.8498 _exptl_absorpt_correction_T_max 0.9529 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_unetI/netI 0.0501 _diffrn_reflns_number 6555 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.964 _reflns_number_total 2499 _reflns_number_gt 2104 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0642P)^2^+0.9059P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.011(3) _refine_ls_number_reflns 2499 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.334 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.17923(5) 0.11714(3) 1.16852(10) 0.0206(2) Uani 1 1 d . . . Cl1 Cl 0.55827(6) 0.11565(4) 0.55198(13) 0.0484(3) Uani 1 1 d . . . O1 O 0.21495(14) 0.07678(8) 1.3801(3) 0.0270(4) Uani 1 1 d . . . O2 O 0.14758(14) 0.18757(8) 1.1984(3) 0.0254(4) Uani 1 1 d . . . F1 F -0.30057(13) 0.10482(8) 0.1387(3) 0.0370(4) Uani 1 1 d . . . F2 F -0.17311(13) 0.16168(9) 0.0021(3) 0.0391(4) Uani 1 1 d . . . F3 F -0.27084(13) 0.21057(7) 0.2310(3) 0.0356(4) Uani 1 1 d . . . N1 N 0.08063(15) 0.07185(9) 1.0161(3) 0.0219(4) Uani 1 1 d . . . N2 N -0.06529(15) 0.05367(9) 0.7140(3) 0.0208(4) Uani 1 1 d D . . H2 H -0.072(2) 0.0140(10) 0.787(4) 0.024(6) Uiso 1 1 d D . . C1 C 0.28882(19) 0.11791(11) 1.0008(4) 0.0208(5) Uani 1 1 d . . . C6 C 0.3376(2) 0.05572(13) 0.9540(4) 0.0271(5) Uani 1 1 d . . . H6 H 0.3141 0.0141 1.0175 0.033 Uiso 1 1 calc R . . C5 C 0.4205(2) 0.05490(14) 0.8142(4) 0.0307(6) Uani 1 1 d . . . H5 H 0.4526 0.0127 0.7761 0.037 Uiso 1 1 calc R . . C4 C 0.4558(2) 0.11649(14) 0.7310(5) 0.0308(6) Uani 1 1 d . . . C3 C 0.4103(2) 0.17860(13) 0.7824(5) 0.0314(6) Uani 1 1 d . . . H3 H 0.4376 0.2204 0.7277 0.038 Uiso 1 1 calc R . . C2 C 0.32454(19) 0.17935(12) 0.9144(4) 0.0260(5) Uani 1 1 d . . . H2A H 0.2904 0.2215 0.9457 0.031 Uiso 1 1 calc R . . C7 C 0.01846(19) 0.09641(11) 0.8151(4) 0.0202(5) Uani 1 1 d . . . C8 C 0.02776(19) 0.15988(11) 0.6965(4) 0.0220(5) Uani 1 1 d . . . H8 H 0.087 0.1906 0.7546 0.026 Uiso 1 1 calc R . . C9 C -0.04812(19) 0.17669(11) 0.5001(4) 0.0207(5) Uani 1 1 d . . . H9 H -0.042 0.2195 0.4228 0.025 Uiso 1 1 calc R . . C10 C -0.13613(19) 0.13117(11) 0.4091(4) 0.0215(5) Uani 1 1 d . . . C11 C -0.14186(19) 0.06947(12) 0.5186(4) 0.0220(5) Uani 1 1 d . . . H11 H -0.1991 0.0377 0.4585 0.026 Uiso 1 1 calc R . . C12 C -0.21984(19) 0.15163(11) 0.1961(4) 0.0231(5) 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 0.0221(3) 0.0153(3) 0.0241(3) 0.00025(19) 0.0031(2) -0.0022(2) Cl1 0.0319(4) 0.0724(6) 0.0450(5) -0.0011(3) 0.0180(3) 0.0051(3) O1 0.0299(9) 0.0241(9) 0.0255(9) 0.0037(6) 0.0004(7) -0.0039(7) O2 0.0275(9) 0.0183(8) 0.0317(9) -0.0025(6) 0.0089(7) -0.0017(7) F1 0.0393(9) 0.0284(8) 0.0378(9) 0.0047(6) -0.0087(7) -0.0095(6) F2 0.0364(9) 0.0574(11) 0.0253(8) 0.0108(7) 0.0103(6) 0.0098(7) F3 0.0410(9) 0.0273(8) 0.0353(8) -0.0036(6) -0.0028(6) 0.0139(6) N1 0.0210(10) 0.0170(9) 0.0265(10) 0.0023(7) 0.0005(8) -0.0025(7) N2 0.0223(10) 0.0142(9) 0.0258(10) 0.0016(7) 0.0039(8) -0.0010(7) C1 0.0185(11) 0.0182(11) 0.0240(11) -0.0012(8) -0.0008(9) 0.0002(8) C6 0.0268(12) 0.0236(12) 0.0292(12) 0.0003(9) -0.0004(10) 0.0034(10) C5 0.0278(13) 0.0313(14) 0.0318(13) -0.0039(10) 0.0018(10) 0.0107(10) C4 0.0192(12) 0.0435(16) 0.0290(13) -0.0002(10) 0.0026(10) 0.0040(11) C3 0.0256(13) 0.0310(13) 0.0375(14) 0.0062(10) 0.0051(11) -0.0029(10) C2 0.0210(12) 0.0204(11) 0.0361(13) 0.0007(10) 0.0036(10) -0.0006(9) C7 0.0209(12) 0.0159(10) 0.0246(11) -0.0005(8) 0.0064(9) 0.0015(9) C8 0.0219(12) 0.0182(11) 0.0271(12) 0.0003(9) 0.0073(9) -0.0023(9) C9 0.0223(12) 0.0161(10) 0.0253(11) 0.0017(8) 0.0087(9) -0.0006(9) C10 0.0230(12) 0.0187(11) 0.0231(11) -0.0003(9) 0.0045(9) 0.0019(9) C11 0.0216(12) 0.0195(11) 0.0248(11) -0.0007(8) 0.0039(9) 0.0004(9) C12 0.0269(13) 0.0193(11) 0.0239(11) 0.0008(8) 0.0062(9) -0.0007(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.4387(16) . ? S1 O2 1.4416(17) . ? S1 N1 1.6143(18) . ? S1 C1 1.764(2) . ? Cl1 C4 1.737(3) . ? F1 C12 1.338(3) . ? F2 C12 1.337(3) . ? F3 C12 1.335(3) . ? N1 C7 1.344(3) . ? N2 C11 1.355(3) . ? N2 C7 1.363(3) . ? N2 H2 0.886(17) . ? C1 C2 1.390(3) . ? C1 C6 1.394(3) . ? C6 C5 1.385(4) . ? C6 H6 0.95 . ? C5 C4 1.384(4) . ? C5 H5 0.95 . ? C4 C3 1.381(4) . ? C3 C2 1.384(4) . ? C3 H3 0.95 . ? C2 H2A 0.95 . ? C7 C8 1.421(3) . ? C8 C9 1.360(3) . ? C8 H8 0.95 . ? C9 C10 1.416(3) . ? C9 H9 0.95 . ? C10 C11 1.360(3) . ? C10 C12 1.494(3) . ? C11 H11 0.95 . ? 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 O1 S1 O2 118.01(10) . . ? O1 S1 N1 103.83(10) . . ? O2 S1 N1 113.20(10) . . ? O1 S1 C1 107.90(10) . . ? O2 S1 C1 107.25(10) . . ? N1 S1 C1 105.97(10) . . ? C7 N1 S1 121.22(16) . . ? C11 N2 C7 124.37(19) . . ? C11 N2 H2 118.4(16) . . ? C7 N2 H2 117.2(16) . . ? C2 C1 C6 120.8(2) . . ? C2 C1 S1 120.51(18) . . ? C6 C1 S1 118.72(18) . . ? C5 C6 C1 119.6(2) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C3 C4 C5 121.8(3) . . ? C3 C4 Cl1 119.0(2) . . ? C5 C4 Cl1 119.1(2) . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C2 C1 119.4(2) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? N1 C7 N2 114.26(19) . . ? N1 C7 C8 129.3(2) . . ? N2 C7 C8 116.48(19) . . ? C9 C8 C7 120.0(2) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.7(2) . . ? C11 C10 C12 121.6(2) . . ? C9 C10 C12 119.7(2) . . ? N2 C11 C10 119.5(2) . . ? N2 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? F3 C12 F2 105.65(18) . . ? F3 C12 F1 106.38(19) . . ? F2 C12 F1 107.21(19) . . ? F3 C12 C10 112.23(18) . . ? F2 C12 C10 112.3(2) . . ? F1 C12 C10 112.63(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.886(17) 2.024(17) 2.907(3) 174(2) 3_557 #----------------------------------------------------------------------------# data_A1_F~CF3_alpha _database_code_depnum_ccdc_archive 'CCDC 871353' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H8 F4 N2 O2 S' _chemical_formula_sum 'C12 H8 F4 N2 O2 S' _chemical_formula_weight 320.26 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1914(9) _cell_length_b 19.0870(15) _cell_length_c 5.9552(3) _cell_angle_alpha 90 _cell_angle_beta 97.357(5) _cell_angle_gamma 90 _cell_volume 1261.62(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 22476 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.9200 _exptl_absorpt_correction_T_max 0.9846 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.1031 _diffrn_reflns_av_unetI/netI 0.0655 _diffrn_reflns_number 9500 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 25.25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.972 _reflns_number_total 2211 _reflns_number_gt 1787 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0881P)^2^+0.2678P] 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_number_reflns 2211 _refine_ls_number_parameters 194 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1381 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.379 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.107 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.20271(6) 0.11555(3) 1.14081(10) 0.0276(2) Uani 1 1 d . . . O1 O 0.24370(17) 0.07369(9) 1.3359(3) 0.0369(5) Uani 1 1 d . . . O2 O 0.16933(17) 0.18708(9) 1.1781(3) 0.0344(5) Uani 1 1 d . . . N1 N 0.09512(19) 0.07024(10) 1.0049(3) 0.0294(5) Uani 1 1 d . . . N2 N -0.06205(18) 0.05402(11) 0.7278(3) 0.0262(5) Uani 1 1 d D . . H2 H -0.075(2) 0.0146(10) 0.796(4) 0.026(7) Uiso 1 1 d D . . F1 F 0.59877(19) 0.11823(16) 0.5902(4) 0.0964(10) Uani 1 1 d . . . F2 F -0.26893(15) 0.21301(8) 0.2641(3) 0.0475(5) Uani 1 1 d . . . F3 F -0.15675(17) 0.16506(10) 0.0488(3) 0.0546(5) Uani 1 1 d . . . F4 F -0.29818(17) 0.10619(9) 0.1710(3) 0.0564(6) Uani 1 1 d . . . C1 C 0.3199(2) 0.11805(12) 0.9683(4) 0.0278(6) Uani 1 1 d . . . C2 C 0.3679(2) 0.18110(15) 0.9114(5) 0.0395(7) Uani 1 1 d . . . H2A H 0.3355 0.224 0.9577 0.047 Uiso 1 1 calc R . . C3 C 0.4643(3) 0.1813(2) 0.7852(6) 0.0584(10) Uani 1 1 d . . . H3 H 0.5011 0.2239 0.7483 0.07 Uiso 1 1 calc R . . C4 C 0.5040(3) 0.1183(2) 0.7163(5) 0.0576(10) Uani 1 1 d . . . C5 C 0.4580(3) 0.0550(2) 0.7663(5) 0.0520(9) Uani 1 1 d . . . H5 H 0.4892 0.0125 0.7141 0.062 Uiso 1 1 calc R . . C6 C 0.3640(3) 0.05496(15) 0.8961(5) 0.0391(7) Uani 1 1 d . . . H6 H 0.3297 0.0119 0.936 0.047 Uiso 1 1 calc R . . C7 C 0.0316(2) 0.09551(12) 0.8159(4) 0.0252(5) Uani 1 1 d . . . C8 C 0.0480(2) 0.15846(12) 0.6981(4) 0.0260(6) Uani 1 1 d . . . H8 H 0.1135 0.1886 0.7493 0.031 Uiso 1 1 calc R . . C9 C -0.0297(2) 0.17605(13) 0.5117(4) 0.0259(6) Uani 1 1 d . . . H9 H -0.0184 0.2187 0.4349 0.031 Uiso 1 1 calc R . . C10 C -0.1269(2) 0.13178(13) 0.4308(4) 0.0265(6) Uani 1 1 d . . . C11 C -0.1405(2) 0.07041(12) 0.5423(4) 0.0267(6) Uani 1 1 d . . . H11 H -0.2045 0.0394 0.4904 0.032 Uiso 1 1 calc R . . C12 C -0.2128(2) 0.15350(13) 0.2306(4) 0.0297(6) 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 0.0284(4) 0.0249(4) 0.0288(4) 0.0012(2) 0.0005(3) -0.0036(3) O1 0.0414(12) 0.0344(10) 0.0317(10) 0.0074(7) -0.0069(8) -0.0066(9) O2 0.0384(11) 0.0295(10) 0.0356(11) -0.0030(7) 0.0059(8) -0.0008(8) N1 0.0299(12) 0.0256(11) 0.0319(11) 0.0043(8) 0.0005(9) -0.0045(9) N2 0.0259(12) 0.0240(11) 0.0284(11) 0.0023(8) 0.0019(9) -0.0009(9) F1 0.0477(13) 0.167(3) 0.0832(16) 0.0480(15) 0.0403(11) 0.0403(14) F2 0.0512(11) 0.0422(10) 0.0454(10) -0.0055(7) -0.0081(8) 0.0207(8) F3 0.0503(11) 0.0843(14) 0.0306(10) 0.0151(8) 0.0104(8) 0.0173(10) F4 0.0642(13) 0.0427(10) 0.0533(11) 0.0132(8) -0.0272(9) -0.0186(9) C1 0.0213(13) 0.0306(14) 0.0294(13) 0.0001(10) -0.0048(10) 0.0016(11) C2 0.0255(15) 0.0377(16) 0.0544(18) 0.0097(12) 0.0013(13) -0.0019(12) C3 0.0336(19) 0.070(2) 0.073(2) 0.0323(19) 0.0112(16) 0.0011(17) C4 0.0284(18) 0.103(3) 0.0424(18) 0.0212(17) 0.0093(14) 0.0198(19) C5 0.0432(19) 0.074(2) 0.0383(17) -0.0043(15) 0.0009(13) 0.0223(17) C6 0.0389(17) 0.0390(16) 0.0373(15) -0.0038(12) -0.0029(12) 0.0055(13) C7 0.0231(14) 0.0253(12) 0.0283(13) -0.0006(10) 0.0071(10) 0.0006(11) C8 0.0245(14) 0.0228(13) 0.0315(14) -0.0002(10) 0.0070(10) -0.0014(10) C9 0.0274(15) 0.0246(13) 0.0273(13) 0.0007(9) 0.0096(10) -0.0005(10) C10 0.0294(14) 0.0248(12) 0.0262(13) -0.0012(10) 0.0070(10) 0.0056(11) C11 0.0227(13) 0.0276(13) 0.0296(13) -0.0016(10) 0.0024(10) 0.0002(10) C12 0.0325(15) 0.0272(14) 0.0295(14) -0.0004(10) 0.0043(11) -0.0034(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.4360(18) . ? S1 O2 1.4402(18) . ? S1 N1 1.613(2) . ? S1 C1 1.767(3) . ? N1 C7 1.342(3) . ? N2 C11 1.357(3) . ? N2 C7 1.364(3) . ? N2 H2 0.874(17) . ? F1 C4 1.376(4) . ? F2 C12 1.325(3) . ? F3 C12 1.337(3) . ? F4 C12 1.329(3) . ? C1 C2 1.378(4) . ? C1 C6 1.390(4) . ? C2 C3 1.391(5) . ? C2 H2A 0.95 . ? C3 C4 1.363(5) . ? C3 H3 0.95 . ? C4 C5 1.362(5) . ? C5 C6 1.383(4) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.415(3) . ? C8 C9 1.362(4) . ? C8 H8 0.95 . ? C9 C10 1.413(4) . ? C9 H9 0.95 . ? C10 C11 1.365(3) . ? C10 C12 1.491(4) . ? C11 H11 0.95 . ? 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 O1 S1 O2 117.71(11) . . ? O1 S1 N1 104.36(11) . . ? O2 S1 N1 113.19(11) . . ? O1 S1 C1 107.54(12) . . ? O2 S1 C1 106.89(11) . . ? N1 S1 C1 106.54(11) . . ? C7 N1 S1 120.63(17) . . ? C11 N2 C7 124.4(2) . . ? C11 N2 H2 116.9(16) . . ? C7 N2 H2 118.7(16) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 S1 120.5(2) . . ? C6 C1 S1 118.4(2) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C4 C3 C2 117.8(3) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C5 C4 C3 124.7(3) . . ? C5 C4 F1 117.2(3) . . ? C3 C4 F1 118.0(3) . . ? C4 C5 C6 117.3(3) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? C5 C6 C1 119.9(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 N2 114.4(2) . . ? N1 C7 C8 129.2(2) . . ? N2 C7 C8 116.4(2) . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.9(2) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 118.5(2) . . ? C11 C10 C12 121.8(2) . . ? C9 C10 C12 119.7(2) . . ? N2 C11 C10 119.5(2) . . ? N2 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? F2 C12 F4 106.5(2) . . ? F2 C12 F3 105.1(2) . . ? F4 C12 F3 106.9(2) . . ? F2 C12 C10 112.8(2) . . ? F4 C12 C10 113.1(2) . . ? F3 C12 C10 111.8(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.874(17) 2.037(18) 2.906(3) 172(2) 3_557 #----------------------------------------------------------------------------# data_A1_Me~CF3 _database_code_depnum_ccdc_archive 'CCDC 871354' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H11 F3 N2 O2 S' _chemical_formula_sum 'C13 H11 F3 N2 O2 S' _chemical_formula_weight 316.3 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1514(11) _cell_length_b 19.549(2) _cell_length_c 5.6316(5) _cell_angle_alpha 90 _cell_angle_beta 99.286(6) _cell_angle_gamma 90 _cell_volume 1320.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17097 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.9235 _exptl_absorpt_correction_T_max 0.9774 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_unetI/netI 0.0593 _diffrn_reflns_number 6911 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 25.08 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.927 _diffrn_measured_fraction_theta_max 0.927 _reflns_number_total 2183 _reflns_number_gt 1587 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0775P)^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_number_reflns 2183 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.117 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.268 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.071 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.18106(6) 0.11693(3) 1.16646(12) 0.0283(3) Uani 1 1 d . . . O1 O 0.21635(17) 0.07644(9) 1.3776(3) 0.0361(5) Uani 1 1 d . . . O2 O 0.14780(16) 0.18645(9) 1.1984(3) 0.0323(5) Uani 1 1 d . . . N1 N 0.08285(18) 0.07201(10) 1.0146(4) 0.0265(6) Uani 1 1 d . . . N2 N -0.06320(18) 0.05299(10) 0.7149(4) 0.0255(6) Uani 1 1 d D . . H2 H -0.070(2) 0.0146(12) 0.796(5) 0.045(9) Uiso 1 1 d D . . C1 C 0.2899(2) 0.11874(12) 0.9967(5) 0.0270(7) Uani 1 1 d . . . C2 C 0.3252(2) 0.18017(14) 0.9105(5) 0.0320(7) Uani 1 1 d . . . H2A H 0.2903 0.221 0.9395 0.038 Uiso 1 1 calc R . . C3 C 0.4122(3) 0.18015(15) 0.7822(6) 0.0383(8) Uani 1 1 d . . . H3 H 0.4378 0.2216 0.7315 0.046 Uiso 1 1 calc R . . C4 C 0.4633(2) 0.11953(16) 0.7256(5) 0.0366(8) Uani 1 1 d . . . C5 C 0.4256(3) 0.05876(15) 0.8137(6) 0.0384(8) Uani 1 1 d . . . H5 H 0.4586 0.0177 0.7802 0.046 Uiso 1 1 calc R . . C6 C 0.3413(2) 0.05797(14) 0.9488(5) 0.0316(7) Uani 1 1 d . . . H6 H 0.3185 0.0168 1.0081 0.038 Uiso 1 1 calc R . . C7 C 0.0195(2) 0.09564(13) 0.8135(5) 0.0240(6) Uani 1 1 d . . . C8 C 0.0285(2) 0.15897(12) 0.6943(5) 0.0255(6) Uani 1 1 d . . . H8 H 0.0861 0.189 0.7506 0.031 Uiso 1 1 calc R . . C9 C -0.0469(2) 0.17548(13) 0.4990(5) 0.0266(6) Uani 1 1 d . . . H9 H -0.0411 0.2172 0.4224 0.032 Uiso 1 1 calc R . . C10 C -0.1338(2) 0.13048(13) 0.4106(5) 0.0250(6) Uani 1 1 d . . . C11 C -0.1382(2) 0.06856(13) 0.5199(5) 0.0269(7) Uani 1 1 d . . . H11 H -0.193 0.0371 0.4597 0.032 Uiso 1 1 calc R . . C12 C 0.5531(3) 0.12034(19) 0.5727(6) 0.0521(10) Uani 1 1 d . . . H12A H 0.5975 0.1608 0.6067 0.078 Uiso 1 1 calc R . . H12B H 0.52 0.1201 0.406 0.078 Uiso 1 1 calc R . . H12C H 0.5994 0.0806 0.6073 0.078 Uiso 1 1 calc R . . C13 C -0.2175(2) 0.15014(13) 0.1992(5) 0.0294(7) Uani 1 1 d . . . F1 F -0.29512(15) 0.10267(8) 0.1375(3) 0.0479(5) Uani 1 1 d . . . F2 F -0.17160(15) 0.16375(9) 0.0044(3) 0.0479(5) Uani 1 1 d . . . F3 F -0.27224(14) 0.20730(8) 0.2398(3) 0.0422(5) 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 0.0325(5) 0.0185(4) 0.0331(4) 0.0015(3) 0.0027(3) -0.0015(3) O1 0.0441(12) 0.0267(10) 0.0337(12) 0.0082(9) -0.0053(9) -0.0055(9) O2 0.0394(12) 0.0201(10) 0.0386(12) -0.0016(8) 0.0100(9) 0.0003(8) N1 0.0262(13) 0.0204(11) 0.0313(13) 0.0041(10) 0.0000(10) -0.0004(10) N2 0.0256(13) 0.0165(12) 0.0343(14) 0.0033(10) 0.0046(11) -0.0010(9) C1 0.0266(15) 0.0201(14) 0.0316(15) 0.0002(11) -0.0034(12) 0.0008(11) C2 0.0253(17) 0.0230(14) 0.0479(19) 0.0007(13) 0.0060(14) 0.0007(12) C3 0.0308(18) 0.0342(17) 0.050(2) 0.0073(14) 0.0055(16) -0.0025(14) C4 0.0264(17) 0.048(2) 0.0334(17) -0.0010(14) -0.0001(14) 0.0039(14) C5 0.0364(19) 0.0337(17) 0.0423(19) -0.0081(14) -0.0019(15) 0.0095(14) C6 0.0331(17) 0.0228(15) 0.0371(18) -0.0002(12) 0.0006(14) 0.0015(12) C7 0.0236(15) 0.0191(13) 0.0305(15) -0.0026(12) 0.0080(12) 0.0009(11) C8 0.0234(15) 0.0164(13) 0.0375(17) 0.0029(11) 0.0073(13) -0.0016(11) C9 0.0306(16) 0.0194(13) 0.0320(16) 0.0024(11) 0.0115(13) 0.0002(11) C10 0.0269(16) 0.0199(13) 0.0299(16) 0.0001(11) 0.0100(13) 0.0032(11) C11 0.0250(15) 0.0215(13) 0.0340(17) -0.0005(11) 0.0040(13) -0.0013(11) C12 0.037(2) 0.072(3) 0.049(2) -0.0016(18) 0.0109(17) 0.0060(17) C13 0.0347(17) 0.0204(14) 0.0332(17) 0.0012(12) 0.0058(14) 0.0000(12) F1 0.0513(12) 0.0280(9) 0.0562(12) 0.0052(8) -0.0157(9) -0.0110(8) F2 0.0499(12) 0.0618(12) 0.0336(11) 0.0111(9) 0.0110(9) 0.0137(9) F3 0.0463(11) 0.0320(9) 0.0454(11) -0.0018(8) -0.0009(9) 0.0154(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.4354(19) . ? S1 O2 1.4374(19) . ? S1 N1 1.612(2) . ? S1 C1 1.753(3) . ? N1 C7 1.345(3) . ? N2 C11 1.344(3) . ? N2 C7 1.354(3) . ? N2 H2 0.889(18) . ? C1 C6 1.389(4) . ? C1 C2 1.389(4) . ? C2 C3 1.373(4) . ? C2 H2A 0.93 . ? C3 C4 1.398(4) . ? C3 H3 0.93 . ? C4 C5 1.393(4) . ? C4 C12 1.495(4) . ? C5 C6 1.372(4) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C7 C8 1.421(4) . ? C8 C9 1.352(4) . ? C8 H8 0.93 . ? C9 C10 1.402(4) . ? C9 H9 0.93 . ? C10 C11 1.363(3) . ? C10 C13 1.486(4) . ? C11 H11 0.93 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 F1 1.329(3) . ? C13 F2 1.335(3) . ? C13 F3 1.339(3) . ? 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 O1 S1 O2 118.03(12) . . ? O1 S1 N1 103.64(11) . . ? O2 S1 N1 112.49(12) . . ? O1 S1 C1 108.20(13) . . ? O2 S1 C1 107.54(12) . . ? N1 S1 C1 106.30(12) . . ? C7 N1 S1 122.29(18) . . ? C11 N2 C7 123.8(2) . . ? C11 N2 H2 120(2) . . ? C7 N2 H2 115(2) . . ? C6 C1 C2 119.9(3) . . ? C6 C1 S1 119.4(2) . . ? C2 C1 S1 120.7(2) . . ? C3 C2 C1 119.4(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 121.9(3) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 117.3(3) . . ? C5 C4 C12 121.7(3) . . ? C3 C4 C12 121.0(3) . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 119.9(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 N2 114.8(2) . . ? N1 C7 C8 128.3(2) . . ? N2 C7 C8 116.8(2) . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.6(2) . . ? C11 C10 C13 121.3(2) . . ? C9 C10 C13 120.0(2) . . ? N2 C11 C10 120.0(2) . . ? N2 C11 H11 120 . . ? C10 C11 H11 120 . . ? C4 C12 H12A 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? F1 C13 F2 107.3(2) . . ? F1 C13 F3 106.0(2) . . ? F2 C13 F3 105.0(2) . . ? F1 C13 C10 113.2(2) . . ? F2 C13 C10 112.8(2) . . ? F3 C13 C10 111.9(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 N1 0.889(18) 2.021(18) 2.910(3) 179(3) 3_557 #----------------------------------------------------------------------------# data_A1_H~CF3_alpha _database_code_depnum_ccdc_archive 'CCDC 871355' #TrackingRef 'CIFs.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H9 F3 N2 O2 S' _chemical_formula_sum 'C12 H9 F3 N2 O2 S' _chemical_formula_weight 302.27 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.8792(8) _cell_length_b 18.802(2) _cell_length_c 6.1463(6) _cell_angle_alpha 90 _cell_angle_beta 95.248(7) _cell_angle_gamma 90 _cell_volume 1252.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8091 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 26.02 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_absorpt_correction_T_min 0.9234 _exptl_absorpt_correction_T_max 0.9852 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 9.091 _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_av_R_equivalents 0.1158 _diffrn_reflns_av_unetI/netI 0.101 _diffrn_reflns_number 5759 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 25.24 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _reflns_number_total 2212 _reflns_number_gt 1682 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0118P)^2^+4.9178P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.045(7) _refine_ls_number_reflns 2212 _refine_ls_number_parameters 218 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.1013 _refine_ls_R_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.813 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.08 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.22324(11) 0.11604(6) 1.1276(2) 0.0384(4) Uani 1 1 d . . . O2 O 0.1847(3) 0.18806(17) 1.1619(6) 0.0491(10) Uani 1 1 d . . . O1 O 0.2617(3) 0.07272(18) 1.3145(5) 0.0477(9) Uani 1 1 d . . . N1 N 0.1137(4) 0.0698(2) 0.9963(7) 0.0447(11) Uani 1 1 d D . . H1 H 0.090(8) 0.038(4) 1.085(12) 0.05(2) Uiso 0.58(7) 1 d PD A 1 N2 N -0.0497(3) 0.0509(2) 0.7457(7) 0.0380(10) Uani 1 1 d D . . H2 H -0.079(10) 0.017(5) 0.825(17) 0.05(2) Uiso 0.42(7) 1 d PD A 2 F1 F -0.2770(8) 0.1986(5) 0.3083(13) 0.083(4) Uani 0.487(12) 1 d PDU B 1 F2 F -0.2659(9) 0.0942(4) 0.1811(13) 0.079(4) Uani 0.487(12) 1 d PDU B 1 F3 F -0.1421(6) 0.1735(5) 0.0933(10) 0.060(3) Uani 0.487(12) 1 d PDU B 1 F1' F -0.3126(4) 0.1224(4) 0.2741(12) 0.057(2) Uani 0.513(12) 1 d PDU B 2 F2' F -0.1644(7) 0.1260(5) 0.0738(9) 0.087(4) Uani 0.513(12) 1 d PDU B 2 F3' F -0.2155(8) 0.2185(2) 0.2414(13) 0.062(3) Uani 0.513(12) 1 d PDU B 2 C1 C 0.3435(5) 0.1203(3) 0.9576(9) 0.0537(14) Uani 1 1 d . . . C2 C 0.3945(5) 0.1857(5) 0.9136(15) 0.098(3) Uani 1 1 d . . . H2A H 0.3569 0.2277 0.9624 0.118 Uiso 1 1 calc R . . C3 C 0.4972(8) 0.1917(7) 0.8023(19) 0.131(4) Uani 1 1 d U . . H3 H 0.5365 0.2361 0.7832 0.157 Uiso 1 1 calc R . . C4 C 0.5382(11) 0.1318(9) 0.7228(19) 0.139(4) Uani 1 1 d U . . H4 H 0.6073 0.1358 0.6397 0.167 Uiso 1 1 calc R . . C5 C 0.4935(9) 0.0654(7) 0.7458(15) 0.120(3) Uani 1 1 d U . . H5 H 0.5287 0.0255 0.6799 0.144 Uiso 1 1 calc R . . C6 C 0.3890(7) 0.0577(5) 0.8760(10) 0.089(3) Uani 1 1 d . . . H6 H 0.354 0.0127 0.9034 0.107 Uiso 1 1 calc R . . C7 C 0.0453(4) 0.0943(2) 0.8131(7) 0.0343(10) Uani 1 1 d . . . C8 C 0.0665(4) 0.1568(2) 0.6978(8) 0.0360(11) Uani 1 1 d . . . H8 H 0.1343 0.1868 0.7435 0.043 Uiso 1 1 calc R . . C9 C -0.0115(4) 0.1739(2) 0.5192(7) 0.0348(10) Uani 1 1 d . . . H9 H 0.0018 0.2162 0.4401 0.042 Uiso 1 1 calc R . . C10 C -0.1111(4) 0.1295(2) 0.4520(7) 0.0341(10) Uani 1 1 d . B . C11 C -0.1267(4) 0.0685(2) 0.5682(8) 0.0376(11) Uani 1 1 d . . . H11 H -0.1934 0.0376 0.523 0.045 Uiso 1 1 calc R . . C12 C -0.1989(4) 0.14860(18) 0.2616(7) 0.0445(12) Uani 1 1 d 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 0.0450(8) 0.0207(6) 0.0478(7) -0.0029(5) -0.0046(5) 0.0044(5) O2 0.058(2) 0.0327(18) 0.049(2) 0.0005(15) -0.0116(16) 0.0033(16) O1 0.064(2) 0.0203(17) 0.062(2) -0.0080(15) -0.0001(18) 0.0060(15) N1 0.050(2) 0.022(2) 0.059(3) 0.0100(19) -0.017(2) -0.0027(18) N2 0.035(2) 0.021(2) 0.058(3) 0.0027(17) -0.0014(18) -0.0040(15) F1 0.067(6) 0.099(7) 0.078(5) -0.028(5) -0.023(4) 0.057(5) F2 0.094(7) 0.058(5) 0.077(6) 0.002(4) -0.039(5) -0.028(5) F3 0.065(4) 0.065(5) 0.048(4) 0.013(4) -0.014(3) -0.011(4) F1' 0.050(4) 0.063(5) 0.056(4) 0.003(3) -0.012(3) 0.007(3) F2' 0.082(6) 0.138(9) 0.042(4) -0.025(5) 0.005(3) 0.045(6) F3' 0.076(5) 0.040(4) 0.067(5) 0.022(3) -0.013(4) 0.008(3) C1 0.036(3) 0.069(4) 0.055(3) 0.011(3) -0.007(2) 0.020(3) C2 0.029(3) 0.103(6) 0.164(8) 0.047(6) 0.011(4) 0.000(3) C3 0.072(5) 0.148(8) 0.173(8) 0.048(7) 0.018(5) 0.013(5) C4 0.114(7) 0.182(9) 0.126(7) 0.034(7) 0.031(6) 0.033(7) C5 0.099(6) 0.163(8) 0.097(5) 0.001(6) 0.004(5) 0.093(6) C6 0.094(5) 0.122(7) 0.050(3) -0.002(4) -0.001(3) 0.071(5) C7 0.035(2) 0.016(2) 0.050(3) 0.0037(18) -0.003(2) 0.0002(17) C8 0.034(2) 0.020(2) 0.053(3) 0.009(2) -0.001(2) 0.0000(18) C9 0.038(2) 0.024(2) 0.043(2) 0.0032(19) 0.008(2) 0.0024(18) C10 0.037(2) 0.024(2) 0.042(2) 0.0001(19) 0.0026(19) 0.0051(18) C11 0.039(2) 0.021(2) 0.052(3) -0.001(2) -0.003(2) -0.0014(18) C12 0.053(3) 0.033(3) 0.046(3) 0.000(2) -0.002(2) 0.011(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 1.439(3) . ? S1 O2 1.439(3) . ? S1 N1 1.628(4) . ? S1 C1 1.750(6) . ? N1 C7 1.371(6) . ? N1 H1 0.86(2) . ? N2 C7 1.352(6) . ? N2 C11 1.354(6) . ? N2 H2 0.88(2) . ? F1 C12 1.317(4) . ? F2 C12 1.326(4) . ? F3 C12 1.337(4) . ? F1' C12 1.339(4) . ? F2' C12 1.316(4) . ? F3' C12 1.331(4) . ? C1 C6 1.386(9) . ? C1 C2 1.387(9) . ? C2 C3 1.367(11) . ? C2 H2A 0.95 . ? C3 C4 1.322(16) . ? C3 H3 0.95 . ? C4 C5 1.352(16) . ? C4 H4 0.95 . ? C5 C6 1.456(12) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.401(6) . ? C8 C9 1.363(6) . ? C8 H8 0.95 . ? C9 C10 1.400(6) . ? C9 H9 0.95 . ? C10 C11 1.371(6) . ? C10 C12 1.486(6) . ? C11 H11 0.95 . ? 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 O1 S1 O2 118.9(2) . . ? O2 S1 N1 111.4(2) . . ? O1 S1 N1 103.9(2) . . ? O2 S1 C1 106.8(3) . . ? O1 S1 C1 108.9(2) . . ? N1 S1 C1 106.4(3) . . ? C7 N1 S1 123.0(3) . . ? C7 N1 H1 125(6) . . ? S1 N1 H1 108(6) . . ? C7 N2 C11 120.0(4) . . ? C7 N2 H2 125(8) . . ? C11 N2 H2 113(8) . . ? C6 C1 C2 121.4(7) . . ? C6 C1 S1 119.2(6) . . ? C2 C1 S1 119.4(5) . . ? C3 C2 C1 122.0(9) . . ? C3 C2 H2A 119 . . ? C1 C2 H2A 119 . . ? C4 C3 C2 115.7(11) . . ? C4 C3 H3 122.2 . . ? C2 C3 H3 122.2 . . ? C3 C4 C5 127.7(11) . . ? C3 C4 H4 116.1 . . ? C5 C4 H4 116.1 . . ? C4 C5 C6 117.1(9) . . ? C4 C5 H5 121.4 . . ? C6 C5 H5 121.4 . . ? C1 C6 C5 115.9(9) . . ? C1 C6 H6 122.1 . . ? C5 C6 H6 122.1 . . ? N2 C7 N1 113.0(4) . . ? N2 C7 C8 120.5(4) . . ? N1 C7 C8 126.5(4) . . ? C9 C8 C7 119.1(4) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.3(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 118.4(4) . . ? C11 C10 C12 120.8(4) . . ? C9 C10 C12 120.8(4) . . ? N2 C11 C10 121.8(4) . . ? N2 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? F2' C12 F1 131.6(6) . . ? F2' C12 F2 67.3(4) . . ? F1 C12 F2 106.8(4) . . ? F2' C12 F3' 106.5(4) . . ? F1 C12 F3' 39.7(4) . . ? F2 C12 F3' 131.5(6) . . ? F2' C12 F3 41.1(4) . . ? F1 C12 F3 105.7(4) . . ? F2 C12 F3 105.0(4) . . ? F3' C12 F3 69.5(4) . . ? F2' C12 F1' 105.7(4) . . ? F1 C12 F1' 68.4(4) . . ? F2 C12 F1' 42.2(4) . . ? F3' C12 F1' 104.5(4) . . ? F3 C12 F1' 131.9(5) . . ? F2' C12 C10 113.4(4) . . ? F1 C12 C10 112.5(5) . . ? F2 C12 C10 113.5(5) . . ? F3' C12 C10 112.6(4) . . ? F3 C12 C10 112.6(4) . . ? F1' C12 C10 113.4(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N2 0.86(2) 2.04(3) 2.891(6) 168(9) 3_557 N2 H2 N1 0.88(2) 2.02(3) 2.891(6) 169(11) 3_557