 
data_No1 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C12 H8 F3 N O S' 
_chemical_formula_sum 
 'C12 H8 F3 N O S' 
_chemical_formula_weight          271.25 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'F'  'F'   0.0171   0.0103 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            61 
_space_group_name_H-M_alt         'P b c a' 
_space_group_name_Hall            '-P 2ac 2ab' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 'x, -y-1/2, z-1/2' 
 '-x-1/2, y-1/2, z' 
  
_cell_length_a                    8.2239(10) 
_cell_length_b                    11.2158(11) 
_cell_length_c                    25.146(3) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      2319.4(5) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     223(2) 
_cell_measurement_reflns_used     9834 
_cell_measurement_theta_min       2.96 
_cell_measurement_theta_max       27.53 
  
_exptl_crystal_description        Plate 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.554 
_exptl_crystal_F_000              1104 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.230 
_exptl_crystal_size_mid           0.150 
_exptl_crystal_size_min           0.050 
_exptl_absorpt_coefficient_mu     0.304 
_shelx_estimated_absorpt_T_min    0.933 
_shelx_estimated_absorpt_T_max    0.985 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.6950 
_exptl_absorpt_correction_T_max   0.7457 
_exptl_absorpt_process_details    'Bruker SADABS'
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       223(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'PHOTON 100 CMOS' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             72285 
_diffrn_reflns_av_unetI/netI      0.0196 
_diffrn_reflns_av_R_equivalents   0.0777 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -33 
_diffrn_reflns_limit_l_max        33 
_diffrn_reflns_theta_min          2.960 
_diffrn_reflns_theta_max          28.376 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.997 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    0.997 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   0.997 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              2893 
_reflns_number_gt                 2165 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0616P)²+3.1391P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2893 
_refine_ls_number_parameters      163 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0823 
_refine_ls_R_factor_gt            0.0588 
_refine_ls_wR_factor_ref          0.1554 
_refine_ls_wR_factor_gt           0.1393 
_refine_ls_goodness_of_fit_ref    1.042 
_refine_ls_restrained_S_all       1.042 
_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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.1297(3) 0.8949(2) 0.16814(9) 0.0303(5) Uani 1 1 d . . . . . 
O1 O 0.1677(2) 0.78929(14) 0.17140(7) 0.0407(4) Uani 1 1 d . . . . . 
C2 C 0.0958(3) 0.96527(19) 0.21491(9) 0.0275(5) Uani 1 1 d . . . . . 
C3 C 0.0079(3) 1.0703(2) 0.21796(10) 0.0324(5) Uani 1 1 d . . . . . 
H3 H -0.0321 1.1130 0.1886 0.039 Uiso 1 1 calc R U . . . 
N1 N -0.0120(3) 1.10223(17) 0.26919(8) 0.0346(5) Uani 1 1 d . . . . . 
H1 H -0.0633 1.1655 0.2801 0.041 Uiso 1 1 calc R U . . . 
C4 C 0.0616(3) 1.0190(2) 0.30178(9) 0.0299(5) Uani 1 1 d . . . . . 
C5 C 0.0724(3) 1.0154(2) 0.35701(10) 0.0403(6) Uani 1 1 d . . . . . 
H5 H 0.0273 1.0761 0.3782 0.048 Uiso 1 1 calc R U . . . 
C6 C 0.1513(4) 0.9204(3) 0.37934(11) 0.0447(7) Uani 1 1 d . . . . . 
H6 H 0.1591 0.9150 0.4166 0.054 Uiso 1 1 calc R U . . . 
C7 C 0.2204(3) 0.8311(2) 0.34778(11) 0.0424(6) Uani 1 1 d . . . . . 
H7 H 0.2732 0.7666 0.3642 0.051 Uiso 1 1 calc R U . . . 
C8 C 0.2125(3) 0.8358(2) 0.29292(10) 0.0335(5) Uani 1 1 d . . . . . 
H8 H 0.2619 0.7765 0.2720 0.040 Uiso 1 1 calc R U . . . 
C9 C 0.1297(3) 0.93061(19) 0.26912(9) 0.0267(5) Uani 1 1 d . . . . . 
C10 C 0.1138(3) 0.9517(2) 0.11444(10) 0.0360(5) Uani 1 1 d . . . . . 
C11 C 0.1454(4) 1.0645(3) 0.10408(12) 0.0511(7) Uani 1 1 d . . . . . 
H11A H 0.1806 1.1155 0.1314 0.061 Uiso 1 1 calc R U . . . 
H11B H 0.1327 1.0940 0.0693 0.061 Uiso 1 1 calc R U . . . 
S1 S 0.05062(10) 0.85419(8) 0.06242(3) 0.0525(2) Uani 1 1 d . . . . . 
C12 C 0.2268(4) 0.8553(3) 0.02128(12) 0.0529(8) Uani 1 1 d . . . . . 
F1 F 0.3587(3) 0.8192(2) 0.04625(10) 0.0839(7) Uani 1 1 d . . . . . 
F2 F 0.2032(3) 0.7803(3) -0.01808(10) 0.1123(11) Uani 1 1 d . . . . . 
F3 F 0.2651(4) 0.9586(2) 0.00136(11) 0.1181(12) Uani 1 1 d . . . . . 
  
  
_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 
C1 O1 1.227(3) . ? 
C1 C2 1.444(3) . ? 
C1 C10 1.499(3) . ? 
C2 C3 1.384(3) . ? 
C2 C9 1.445(3) . ? 
C3 N1 1.347(3) . ? 
C3 H3 0.9400 . ? 
N1 C4 1.382(3) . ? 
N1 H1 0.8700 . ? 
C4 C5 1.392(3) . ? 
C4 C9 1.404(3) . ? 
C5 C6 1.368(4) . ? 
C5 H5 0.9400 . ? 
C6 C7 1.398(4) . ? 
C6 H6 0.9400 . ? 
C7 C8 1.382(4) . ? 
C7 H7 0.9400 . ? 
C8 C9 1.397(3) . ? 
C8 H8 0.9400 . ? 
C10 C11 1.318(4) . ? 
C10 S1 1.782(2) . ? 
C11 H11A 0.9400 . ? 
C11 H11B 0.9400 . ? 
S1 C12 1.780(3) . ? 
C12 F3 1.301(4) . ? 
C12 F2 1.313(4) . ? 
C12 F1 1.318(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 C1 C2 121.5(2) . . ? 
O1 C1 C10 119.5(2) . . ? 
C2 C1 C10 119.0(2) . . ? 
C3 C2 C1 127.7(2) . . ? 
C3 C2 C9 106.1(2) . . ? 
C1 C2 C9 125.8(2) . . ? 
N1 C3 C2 110.0(2) . . ? 
N1 C3 H3 125.0 . . ? 
C2 C3 H3 125.0 . . ? 
C3 N1 C4 109.54(19) . . ? 
C3 N1 H1 125.2 . . ? 
C4 N1 H1 125.2 . . ? 
N1 C4 C5 129.7(2) . . ? 
N1 C4 C9 107.7(2) . . ? 
C5 C4 C9 122.5(2) . . ? 
C6 C5 C4 117.5(2) . . ? 
C6 C5 H5 121.2 . . ? 
C4 C5 H5 121.2 . . ? 
C5 C6 C7 121.2(2) . . ? 
C5 C6 H6 119.4 . . ? 
C7 C6 H6 119.4 . . ? 
C8 C7 C6 121.3(2) . . ? 
C8 C7 H7 119.3 . . ? 
C6 C7 H7 119.3 . . ? 
C7 C8 C9 118.7(2) . . ? 
C7 C8 H8 120.7 . . ? 
C9 C8 H8 120.7 . . ? 
C8 C9 C4 118.8(2) . . ? 
C8 C9 C2 134.7(2) . . ? 
C4 C9 C2 106.56(19) . . ? 
C11 C10 C1 124.7(2) . . ? 
C11 C10 S1 120.1(2) . . ? 
C1 C10 S1 115.19(17) . . ? 
C10 C11 H11A 120.0 . . ? 
C10 C11 H11B 120.0 . . ? 
H11A C11 H11B 120.0 . . ? 
C12 S1 C10 100.66(14) . . ? 
F3 C12 F2 108.4(3) . . ? 
F3 C12 F1 104.9(3) . . ? 
F2 C12 F1 106.5(3) . . ? 
F3 C12 S1 115.3(2) . . ? 
F2 C12 S1 108.3(2) . . ? 
F1 C12 S1 113.0(2) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
O1 C1 C2 C3 -159.2(2) . . . . ? 
C10 C1 C2 C3 19.3(4) . . . . ? 
O1 C1 C2 C9 11.9(4) . . . . ? 
C10 C1 C2 C9 -169.6(2) . . . . ? 
C1 C2 C3 N1 173.3(2) . . . . ? 
C9 C2 C3 N1 0.8(3) . . . . ? 
C2 C3 N1 C4 -0.3(3) . . . . ? 
C3 N1 C4 C5 179.8(3) . . . . ? 
C3 N1 C4 C9 -0.4(3) . . . . ? 
N1 C4 C5 C6 179.0(2) . . . . ? 
C9 C4 C5 C6 -0.9(4) . . . . ? 
C4 C5 C6 C7 0.9(4) . . . . ? 
C5 C6 C7 C8 0.4(4) . . . . ? 
C6 C7 C8 C9 -1.7(4) . . . . ? 
C7 C8 C9 C4 1.7(3) . . . . ? 
C7 C8 C9 C2 -179.8(2) . . . . ? 
N1 C4 C9 C8 179.7(2) . . . . ? 
C5 C4 C9 C8 -0.4(3) . . . . ? 
N1 C4 C9 C2 0.8(2) . . . . ? 
C5 C4 C9 C2 -179.3(2) . . . . ? 
C3 C2 C9 C8 -179.6(3) . . . . ? 
C1 C2 C9 C8 7.7(4) . . . . ? 
C3 C2 C9 C4 -1.0(2) . . . . ? 
C1 C2 C9 C4 -173.7(2) . . . . ? 
O1 C1 C10 C11 -148.3(3) . . . . ? 
C2 C1 C10 C11 33.1(4) . . . . ? 
O1 C1 C10 S1 30.6(3) . . . . ? 
C2 C1 C10 S1 -147.96(19) . . . . ? 
C11 C10 S1 C12 63.9(3) . . . . ? 
C1 C10 S1 C12 -115.1(2) . . . . ? 
C10 S1 C12 F3 -62.3(3) . . . . ? 
C10 S1 C12 F2 176.1(3) . . . . ? 
C10 S1 C12 F1 58.4(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 
N1 H1 O1  0.87 2.04 2.876(3) 161.5 3 
  
_refine_diff_density_max    1.103 
_refine_diff_density_min   -0.607 
_refine_diff_density_rms    0.065 
  
  
  
