data_ds
_audit_creation_date               2019-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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           'C23 H20 Cl F2 N O4 S'
_chemical_formula_sum              'C23 H20 Cl F2 N O4 S'
_chemical_formula_weight           479.91
_chemical_absolute_configuration   rm
_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'
 'Cl' 'Cl' 0.1484 0.1585 '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        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     5.5826(8)
_cell_length_b                     16.132(2)
_cell_length_c                     11.8958(13)
_cell_angle_alpha                  90
_cell_angle_beta                   90.12(5)
_cell_angle_gamma                  90
_cell_volume                       1071.3(2)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      4059
_cell_measurement_temperature      170
_cell_measurement_theta_max        25.505
_cell_measurement_theta_min        2.525
_shelx_estimated_absorpt_T_max     0.974
_shelx_estimated_absorpt_T_min     0.941
_exptl_absorpt_coefficient_mu      0.325
_exptl_absorpt_correction_T_max    0.7454
_exptl_absorpt_correction_T_min    0.6926
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0905 before and 0.0580 after correction. The Ratio of minimum to maximum transmission is 0.9292. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.488
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               496
_exptl_crystal_size_max            0.19
_exptl_crystal_size_mid            0.12
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0518
_diffrn_reflns_av_unetI/netI       0.0626
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.991
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -6
_diffrn_reflns_limit_k_max         19
_diffrn_reflns_limit_k_min         -20
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -14
_diffrn_reflns_number              12417
_diffrn_reflns_point_group_measured_fraction_full  0.981
_diffrn_reflns_point_group_measured_fraction_max  0.959
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.564
_diffrn_reflns_theta_min           2.525
_diffrn_ambient_temperature        170.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.991
_diffrn_measurement_device_type    'D8 VENTURE'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.866
_reflns_Friedel_fraction_full      0.962
_reflns_Friedel_fraction_max       0.924
_reflns_number_gt                  3351
_reflns_number_total               4273
_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         'SAINT V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_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           0.247
_refine_diff_density_min           -0.317
_refine_diff_density_rms           0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.07(5)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       290
_refine_ls_number_reflns           4273
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0685
_refine_ls_R_factor_gt             0.0434
_refine_ls_restrained_S_all        1.035
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0405P)²+0.1790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0836
_refine_ls_wR_factor_ref           0.0982
_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:
 C8(H8), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C16(H16), C19(H19), C21(H21), C12(H12), C18(H18), C13(H13),
 C14(H14), C15(H15), C1(H1A), C4(H4), C5(H5), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_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 0.55533(19) 0.46500(8) 0.51198(9) 0.0294(3) Uani 1 1 d . . . . .
 Cl1 Cl 0.8607(2) 0.46255(8) 0.06600(9) 0.0347(3) Uani 1 1 d . . . . .
 F2 F 0.9402(5) 0.38823(16) 0.4369(2) 0.0350(7) Uani 1 1 d . . . . .
 F1 F 0.5991(5) 0.33950(15) 0.3822(2) 0.0373(7) Uani 1 1 d . . . . .
 O2 O 0.3610(6) 0.5048(2) 0.4549(3) 0.0375(8) Uani 1 1 d . . . . .
 O3 O 0.3769(6) 0.3789(2) 0.1742(3) 0.0362(8) Uani 1 1 d . . . . .
 O4 O 0.8605(6) 0.85971(19) 0.2016(3) 0.0394(9) Uani 1 1 d . . . . .
 O1 O 0.5112(7) 0.4026(2) 0.5950(3) 0.0450(9) Uani 1 1 d . . . . .
 N1 N 0.9186(7) 0.5241(2) 0.3070(3) 0.0277(9) Uani 1 1 d . . . . .
 H1 H 1.053982 0.509419 0.339308 0.033 Uiso 1 1 calc R . . . .
 C17 C 0.8918(8) 0.6074(3) 0.2781(3) 0.0239(10) Uani 1 1 d . . . . .
 C22 C 1.0712(8) 0.6633(3) 0.3097(4) 0.0281(11) Uani 1 1 d . . . . .
 H22 H 1.206848 0.643575 0.349951 0.034 Uiso 1 1 calc R . . . .
 C11 C 0.6120(8) 0.2663(3) 0.1116(4) 0.0240(10) Uani 1 1 d . . . . .
 C16 C 0.4355(9) 0.2072(3) 0.1290(4) 0.0287(11) Uani 1 1 d . . . . .
 H16 H 0.296956 0.221123 0.171227 0.034 Uiso 1 1 calc R . . . .
 C10 C 0.5757(8) 0.3502(3) 0.1587(4) 0.0252(10) Uani 1 1 d . . . . .
 C19 C 0.6786(9) 0.7227(3) 0.1953(4) 0.0305(11) Uani 1 1 d . . . . .
 H19 H 0.542044 0.742970 0.156198 0.037 Uiso 1 1 calc R . . . .
 C21 C 1.0557(9) 0.7458(3) 0.2838(4) 0.0313(11) Uani 1 1 d . . . . .
 H21 H 1.180834 0.782339 0.305672 0.038 Uiso 1 1 calc R . . . .
 C20 C 0.8580(9) 0.7767(3) 0.2257(4) 0.0283(11) Uani 1 1 d . . . . .
 C12 C 0.8146(9) 0.2452(3) 0.0483(4) 0.0293(11) Uani 1 1 d . . . . .
 H12 H 0.938681 0.284651 0.037496 0.035 Uiso 1 1 calc R . . . .
 C8 C 0.7448(7) 0.4610(3) 0.2885(3) 0.0239(9) Uani 1 1 d . . . . .
 H8 H 0.587365 0.488613 0.274037 0.029 Uiso 1 1 calc R . . . .
 C18 C 0.6947(8) 0.6385(3) 0.2214(4) 0.0262(10) Uani 1 1 d . . . . .
 H18 H 0.568854 0.602143 0.199869 0.031 Uiso 1 1 calc R . . . .
 C13 C 0.8340(8) 0.1669(3) 0.0017(4) 0.0302(11) Uani 1 1 d . . . . .
 H13 H 0.968886 0.153355 -0.043291 0.036 Uiso 1 1 calc R . . . .
 C7 C 0.7226(8) 0.4113(3) 0.3978(4) 0.0280(10) Uani 1 1 d . . . . .
 C14 C 0.6580(9) 0.1085(3) 0.0203(4) 0.0299(11) Uani 1 1 d . . . . .
 H14 H 0.672567 0.054736 -0.011483 0.036 Uiso 1 1 calc R . . . .
 C15 C 0.4594(9) 0.1282(3) 0.0854(4) 0.0317(11) Uani 1 1 d . . . . .
 H15 H 0.340543 0.087429 0.099863 0.038 Uiso 1 1 calc R . . . .
 C9 C 0.7958(8) 0.4021(3) 0.1893(3) 0.0249(10) Uani 1 1 d . . . . .
 H9 H 0.934113 0.365036 0.207599 0.030 Uiso 1 1 calc R . . . .
 C6 C 0.7432(8) 0.5412(3) 0.5677(4) 0.0294(11) Uani 1 1 d . . . . .
 C1 C 0.7098(10) 0.6229(3) 0.5362(4) 0.0377(12) Uani 1 1 d . . . . .
 H1A H 0.587114 0.637212 0.484264 0.045 Uiso 1 1 calc R . . . .
 C4 C 1.0679(10) 0.5796(4) 0.6845(5) 0.0499(15) Uani 1 1 d . . . . .
 H4 H 1.192915 0.565560 0.735358 0.060 Uiso 1 1 calc R . . . .
 C5 C 0.9216(9) 0.5175(3) 0.6428(4) 0.0399(13) Uani 1 1 d . . . . .
 H5 H 0.942191 0.461215 0.664419 0.048 Uiso 1 1 calc R . . . .
 C23 C 0.6608(10) 0.8917(3) 0.1423(4) 0.0433(13) Uani 1 1 d . . . . .
 H23A H 0.648465 0.864344 0.068985 0.065 Uiso 1 1 calc GR . . . .
 H23B H 0.681275 0.951501 0.131403 0.065 Uiso 1 1 calc GR . . . .
 H23C H 0.514540 0.881430 0.185521 0.065 Uiso 1 1 calc GR . . . .
 C3 C 1.0368(11) 0.6613(4) 0.6540(5) 0.0512(16) Uani 1 1 d . . . . .
 H3 H 1.140701 0.702540 0.683766 0.061 Uiso 1 1 calc R . . . .
 C2 C 0.8573(11) 0.6839(3) 0.5813(5) 0.0483(15) Uani 1 1 d . . . . .
 H2 H 0.834158 0.740424 0.561904 0.058 Uiso 1 1 calc R . . . .


_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 1.430(3) . ?
 S1 O1 1.432(3) . ?
 S1 C7 1.863(5) . ?
 S1 C6 1.745(5) . ?
 Cl1 C9 1.799(4) . ?
 F2 C7 1.352(5) . ?
 F1 C7 1.360(5) . ?
 O3 C10 1.217(5) . ?
 O4 C20 1.370(5) . ?
 O4 C23 1.415(6) . ?
 N1 C17 1.394(6) . ?
 N1 C8 1.423(6) . ?
 C17 C22 1.399(6) . ?
 C17 C18 1.384(6) . ?
 C22 C21 1.369(6) . ?
 C11 C16 1.388(6) . ?
 C11 C10 1.479(6) . ?
 C11 C12 1.402(6) . ?
 C16 C15 1.383(7) . ?
 C10 C9 1.530(6) . ?
 C19 C20 1.375(7) . ?
 C19 C18 1.396(6) . ?
 C21 C20 1.393(7) . ?
 C12 C13 1.384(6) . ?
 C8 C7 1.534(6) . ?
 C8 C9 1.543(6) . ?
 C13 C14 1.379(7) . ?
 C14 C15 1.390(7) . ?
 C6 C1 1.383(7) . ?
 C6 C5 1.390(7) . ?
 C1 C2 1.389(7) . ?
 C4 C5 1.385(8) . ?
 C4 C3 1.378(9) . ?
 C3 C2 1.372(8) . ?

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 120.7(2) . . ?
 O2 S1 C7 104.11(19) . . ?
 O2 S1 C6 108.6(2) . . ?
 O1 S1 C7 105.2(2) . . ?
 O1 S1 C6 109.7(2) . . ?
 C6 S1 C7 107.6(2) . . ?
 C20 O4 C23 116.9(4) . . ?
 C17 N1 C8 125.4(4) . . ?
 N1 C17 C22 118.6(4) . . ?
 C18 C17 N1 123.7(4) . . ?
 C18 C17 C22 117.7(4) . . ?
 C21 C22 C17 121.5(4) . . ?
 C16 C11 C10 118.3(4) . . ?
 C16 C11 C12 119.1(4) . . ?
 C12 C11 C10 122.5(4) . . ?
 C15 C16 C11 120.6(4) . . ?
 O3 C10 C11 122.1(4) . . ?
 O3 C10 C9 119.2(4) . . ?
 C11 C10 C9 118.7(4) . . ?
 C20 C19 C18 120.7(5) . . ?
 C22 C21 C20 120.6(4) . . ?
 O4 C20 C19 124.9(5) . . ?
 O4 C20 C21 116.4(4) . . ?
 C19 C20 C21 118.7(4) . . ?
 C13 C12 C11 120.1(4) . . ?
 N1 C8 C7 107.4(3) . . ?
 N1 C8 C9 115.6(3) . . ?
 C7 C8 C9 110.0(4) . . ?
 C17 C18 C19 120.8(4) . . ?
 C14 C13 C12 120.1(4) . . ?
 F2 C7 S1 109.2(3) . . ?
 F2 C7 F1 105.5(3) . . ?
 F2 C7 C8 111.2(4) . . ?
 F1 C7 S1 103.9(3) . . ?
 F1 C7 C8 111.8(4) . . ?
 C8 C7 S1 114.6(3) . . ?
 C13 C14 C15 120.2(4) . . ?
 C16 C15 C14 119.8(4) . . ?
 C10 C9 Cl1 105.4(3) . . ?
 C10 C9 C8 111.7(3) . . ?
 C8 C9 Cl1 109.1(3) . . ?
 C1 C6 S1 119.2(4) . . ?
 C1 C6 C5 122.2(5) . . ?
 C5 C6 S1 118.6(4) . . ?
 C6 C1 C2 119.4(5) . . ?
 C3 C4 C5 121.6(5) . . ?
 C4 C5 C6 116.9(5) . . ?
 C2 C3 C4 120.7(5) . . ?
 C3 C2 C1 119.2(6) . . ?


_olex2_submission_special_instructions  'No special instructions were received'
