data_4
_audit_creation_date               2018-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C12 H16 F N O2 S'
_chemical_formula_sum              'C12 H16 F N O2 S'
_chemical_formula_weight           257.32
_chemical_absolute_configuration   syn
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
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'

_cell_length_a                     7.3373(7)
_cell_length_b                     10.0709(8)
_cell_length_c                     17.0758(16)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1261.8(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      3897
_cell_measurement_temperature      100.01(10)
_cell_measurement_theta_max        28.2370
_cell_measurement_theta_min        2.3420
_shelx_estimated_absorpt_T_max     0.972
_shelx_estimated_absorpt_T_min     0.967
_exptl_absorpt_coefficient_mu      0.259
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.80219
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.355
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               544
_exptl_crystal_size_max            0.13
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.11
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0427
_diffrn_reflns_av_unetI/netI       0.0434
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         6
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -20
_diffrn_reflns_number              8072
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          24.996
_diffrn_reflns_theta_max           24.996
_diffrn_reflns_theta_min           2.348
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.01(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   5.2684
_diffrn_detector_type              AtlasS2
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -59.00  34.00   1.00    1.00    --   11.74 -57.00-120.00   93
  2  ω    -15.00  75.00   1.00    1.00    --   11.74  77.00 150.00   90
  3  ω    -16.00  79.00   1.00    1.00    --   11.74  57.00  30.00   95
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0658517000
_diffrn_orient_matrix_UB_12        0.0492488000
_diffrn_orient_matrix_UB_13        0.0090406000
_diffrn_orient_matrix_UB_21        0.0003241000
_diffrn_orient_matrix_UB_22        -0.0211091000
_diffrn_orient_matrix_UB_23        0.0396538000
_diffrn_orient_matrix_UB_31        0.0706279000
_diffrn_orient_matrix_UB_32        -0.0457486000
_diffrn_orient_matrix_UB_33        -0.0085881000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage           0.699
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       1.000
_reflns_number_gt                  2055
_reflns_number_total               2216
_reflns_odcompleteness_completeness  99.93
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       26.32
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.316
_refine_diff_density_min           -0.263
_refine_diff_density_rms           0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.14(6)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.013
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       157
_refine_ls_number_reflns           2216
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0399
_refine_ls_R_factor_gt             0.0363
_refine_ls_restrained_S_all        1.013
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0376P)²+0.3752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0783
_refine_ls_wR_factor_ref           0.0803
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C6(H6), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 S1 S 0.38617(11) 0.64457(7) 0.55418(4) 0.0163(2) Uani 1 1 d . . . . .
 F1 F 0.8809(3) 0.45817(16) 0.48384(10) 0.0242(5) Uani 1 1 d . . . . .
 O2 O 0.3898(4) 0.7505(2) 0.49360(12) 0.0202(5) Uani 1 1 d . . . . .
 O1 O 0.4804(3) 0.3655(2) 0.58266(13) 0.0220(5) Uani 1 1 d . . . . .
 N1 N 0.5904(4) 0.5664(2) 0.54446(14) 0.0168(6) Uani 1 1 d . . . . .
 H1 H 0.687382 0.611342 0.534658 0.020 Uiso 1 1 calc R . . . .
 C1 C 0.8728(5) 0.2893(3) 0.58097(16) 0.0157(7) Uani 1 1 d . . . . .
 C2 C 0.8292(4) 0.1574(3) 0.59647(19) 0.0189(7) Uani 1 1 d . . . . .
 H2 H 0.734178 0.116516 0.569708 0.023 Uiso 1 1 calc R . . . .
 C7 C 0.7681(5) 0.3642(3) 0.51909(18) 0.0178(7) Uani 1 1 d . . . . .
 H7 H 0.729110 0.300835 0.478903 0.021 Uiso 1 1 calc R . . . .
 C10 C 0.5799(5) 0.8230(3) 0.64421(19) 0.0220(8) Uani 1 1 d . . . . .
 H10A H 0.690741 0.773024 0.639741 0.033 Uiso 1 1 calc GR . . . .
 H10B H 0.584067 0.876623 0.690674 0.033 Uiso 1 1 calc GR . . . .
 H10C H 0.566380 0.879306 0.599196 0.033 Uiso 1 1 calc GR . . . .
 C3 C 0.9276(5) 0.0874(3) 0.6518(2) 0.0230(8) Uani 1 1 d . . . . .
 H3 H 0.898414 -0.000729 0.662091 0.028 Uiso 1 1 calc R . . . .
 C8 C 0.5988(5) 0.4317(3) 0.55234(17) 0.0169(7) Uani 1 1 d . . . . .
 C9 C 0.4191(5) 0.7285(3) 0.64898(17) 0.0182(8) Uani 1 1 d . . . . .
 C6 C 1.0136(5) 0.3499(4) 0.62186(19) 0.0219(7) Uani 1 1 d . . . . .
 H6 H 1.042180 0.438448 0.612375 0.026 Uiso 1 1 calc R . . . .
 C5 C 1.1110(6) 0.2782(3) 0.67672(18) 0.0250(8) Uani 1 1 d . . . . .
 H5 H 1.205942 0.318642 0.703808 0.030 Uiso 1 1 calc R . . . .
 C11 C 0.2409(5) 0.8039(3) 0.6616(2) 0.0249(8) Uani 1 1 d . . . . .
 H11A H 0.232129 0.874777 0.624186 0.037 Uiso 1 1 calc GR . . . .
 H11B H 0.238704 0.840008 0.713629 0.037 Uiso 1 1 calc GR . . . .
 H11C H 0.139925 0.744384 0.654923 0.037 Uiso 1 1 calc GR . . . .
 C4 C 1.0686(5) 0.1471(3) 0.69164(19) 0.0260(8) Uani 1 1 d . . . . .
 H4 H 1.134979 0.099308 0.728492 0.031 Uiso 1 1 calc R . . . .
 C12 C 0.4439(5) 0.6207(3) 0.71044(19) 0.0248(8) Uani 1 1 d . . . . .
 H12A H 0.343175 0.560039 0.708065 0.037 Uiso 1 1 calc GR . . . .
 H12B H 0.448858 0.660537 0.761481 0.037 Uiso 1 1 calc GR . . . .
 H12C H 0.555303 0.573629 0.700577 0.037 Uiso 1 1 calc GR . . . .


_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 1.486(2) . ?
 S1 N1 1.700(3) . ?
 S1 C9 1.842(3) . ?
 F1 C7 1.394(4) . ?
 O1 C8 1.211(4) . ?
 N1 C8 1.364(4) . ?
 C1 C2 1.391(4) . ?
 C1 C7 1.508(4) . ?
 C1 C6 1.388(5) . ?
 C2 C3 1.382(5) . ?
 C7 C8 1.526(5) . ?
 C10 C9 1.518(5) . ?
 C3 C4 1.377(5) . ?
 C9 C11 1.528(5) . ?
 C9 C12 1.520(4) . ?
 C6 C5 1.382(5) . ?
 C5 C4 1.380(5) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O2 S1 N1 104.39(14) . . ?
 O2 S1 C9 106.28(13) . . ?
 N1 S1 C9 100.51(15) . . ?
 C8 N1 S1 119.4(2) . . ?
 C2 C1 C7 119.6(3) . . ?
 C2 C1 C6 119.7(3) . . ?
 C6 C1 C7 120.7(3) . . ?
 C3 C2 C1 119.8(3) . . ?
 F1 C7 C1 109.9(3) . . ?
 F1 C7 C8 110.0(2) . . ?
 C1 C7 C8 112.1(2) . . ?
 C4 C3 C2 120.5(3) . . ?
 O1 C8 N1 123.9(3) . . ?
 O1 C8 C7 119.8(3) . . ?
 N1 C8 C7 116.3(3) . . ?
 C10 C9 S1 110.0(2) . . ?
 C10 C9 C11 111.1(3) . . ?
 C10 C9 C12 113.1(3) . . ?
 C11 C9 S1 103.9(2) . . ?
 C12 C9 S1 107.2(2) . . ?
 C12 C9 C11 111.1(3) . . ?
 C5 C6 C1 119.7(3) . . ?
 C4 C5 C6 120.6(3) . . ?
 C3 C4 C5 119.7(3) . . ?


_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.393
_oxdiff_exptl_absorpt_empirical_full_min  0.799
