data_190102_qj4_48_1_0m
_audit_creation_date               2019-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
_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           'C H Cl3, C25 H19 F N2 O4 S'
_chemical_formula_sum              'C26 H20 Cl3 F N2 O4 S'
_chemical_formula_weight           581.85
_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             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_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                     6.1110(3)
_cell_length_b                     16.2539(9)
_cell_length_c                     26.4398(13)
_cell_angle_alpha                  90
_cell_angle_beta                   94.775(2)
_cell_angle_gamma                  90
_cell_volume                       2617.1(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9943
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        30.27
_cell_measurement_theta_min        2.51
_shelx_estimated_absorpt_T_max     0.919
_shelx_estimated_absorpt_T_min     0.777
_exptl_absorpt_coefficient_mu      0.474
_exptl_absorpt_correction_T_max    0.7461
_exptl_absorpt_correction_T_min    0.6064
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1465 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8128.
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      1.477
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1192
_exptl_crystal_size_max            0.561
_exptl_crystal_size_mid            0.42
_exptl_crystal_size_min            0.182
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0413
_diffrn_reflns_av_unetI/netI       0.0400
_diffrn_reflns_Laue_measured_fraction_full  0.993
_diffrn_reflns_Laue_measured_fraction_max  0.992
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         23
_diffrn_reflns_limit_k_min         -22
_diffrn_reflns_limit_l_max         37
_diffrn_reflns_limit_l_min         -37
_diffrn_reflns_number              31783
_diffrn_reflns_point_group_measured_fraction_full  0.993
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           30.564
_diffrn_reflns_theta_min           2.506
_diffrn_ambient_temperature        295.7
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.993
_diffrn_measured_fraction_theta_max  0.992
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_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           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  6105
_reflns_number_total               7964
_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           0.639
_refine_diff_density_min           -0.635
_refine_diff_density_rms           0.075
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       336
_refine_ls_number_reflns           7964
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0843
_refine_ls_R_factor_gt             0.0688
_refine_ls_restrained_S_all        1.069
_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)+(0.1112P)²+1.3905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2022
_refine_ls_wR_factor_ref           0.2163
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_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
 Cl1 Cl 0.6234(3) 0.69838(13) 0.99383(7) 0.1439(7) Uani 1 1 d . . . . .
 Cl2 Cl 1.0385(2) 0.65885(11) 0.95963(7) 0.1327(6) Uani 1 1 d . . . . .
 Cl3 Cl 0.7195(3) 0.53301(11) 0.96427(8) 0.1456(7) Uani 1 1 d . . . . .
 C26 C 0.7602(8) 0.6355(3) 0.95305(16) 0.0911(12) Uani 1 1 d . . . . .
 H26 H 0.703777 0.647652 0.918066 0.109 Uiso 1 1 calc R . . . .
 S1 S 0.64558(8) 0.68423(3) 0.68122(2) 0.03761(15) Uani 1 1 d . . . . .
 F1 F 1.1149(2) 0.59419(9) 0.73769(5) 0.0474(3) Uani 1 1 d . . . . .
 O1 O 0.6369(3) 0.66762(11) 0.83336(7) 0.0501(4) Uani 1 1 d . . . . .
 O2 O 1.1264(3) 0.82090(11) 0.79592(7) 0.0508(4) Uani 1 1 d . . . . .
 O3 O 0.8691(3) 0.70139(13) 0.67191(7) 0.0534(4) Uani 1 1 d . . . . .
 O4 O 0.5279(3) 0.74641(11) 0.70644(7) 0.0506(4) Uani 1 1 d . . . . .
 N1 N 0.6923(3) 0.49736(11) 0.76963(7) 0.0385(4) Uani 1 1 d . . . . .
 N2 N 0.6147(3) 0.59669(12) 0.70878(7) 0.0390(4) Uani 1 1 d . . . . .
 C1 C 1.1860(5) 0.53296(18) 0.85032(10) 0.0554(6) Uani 1 1 d . . . . .
 H1 H 1.292117 0.574005 0.853992 0.067 Uiso 1 1 calc R . . . .
 C2 C 1.1976(6) 0.4622(2) 0.88139(12) 0.0703(9) Uani 1 1 d . . . . .
 H2 H 1.313225 0.456316 0.906312 0.084 Uiso 1 1 calc R . . . .
 C3 C 1.0410(7) 0.4023(2) 0.87526(13) 0.0744(10) Uani 1 1 d . . . . .
 H3 H 1.054663 0.355793 0.895807 0.089 Uiso 1 1 calc R . . . .
 C4 C 0.8616(6) 0.40820(17) 0.83941(11) 0.0601(7) Uani 1 1 d . . . . .
 H4 H 0.754347 0.367548 0.835892 0.072 Uiso 1 1 calc R . . . .
 C5 C 0.8518(4) 0.47757(14) 0.80941(9) 0.0431(5) Uani 1 1 d . . . . .
 C6 C 1.0102(4) 0.53845(14) 0.81429(9) 0.0424(5) Uani 1 1 d . . . . .
 C7 C 0.9601(3) 0.60155(13) 0.77343(8) 0.0373(4) Uani 1 1 d . . . . .
 C8 C 0.7380(3) 0.56941(12) 0.74743(7) 0.0342(4) Uani 1 1 d . . . . .
 C9 C 0.9570(3) 0.68912(13) 0.79138(8) 0.0355(4) Uani 1 1 d . . . . .
 C10 C 0.7837(3) 0.71471(13) 0.82217(8) 0.0360(4) Uani 1 1 d . . . . .
 C11 C 0.7979(4) 0.80075(13) 0.83886(8) 0.0373(4) Uani 1 1 d . . . . .
 C12 C 0.9688(4) 0.85015(14) 0.82522(8) 0.0409(4) Uani 1 1 d . . . . .
 C13 C 1.1142(4) 0.74204(15) 0.78024(9) 0.0440(5) Uani 1 1 d . . . . .
 H13 H 1.222070 0.723039 0.760333 0.053 Uiso 1 1 calc R . . . .
 C14 C 0.6426(4) 0.83561(16) 0.86832(9) 0.0487(5) Uani 1 1 d . . . . .
 H14 H 0.526780 0.803877 0.878109 0.058 Uiso 1 1 calc R . . . .
 C15 C 0.6606(5) 0.91706(18) 0.88294(11) 0.0598(7) Uani 1 1 d . . . . .
 H15 H 0.556370 0.940022 0.902421 0.072 Uiso 1 1 calc R . . . .
 C16 C 0.8327(6) 0.96458(16) 0.86878(11) 0.0592(7) Uani 1 1 d . . . . .
 H16 H 0.842991 1.019377 0.878826 0.071 Uiso 1 1 calc R . . . .
 C17 C 0.9881(5) 0.93212(15) 0.84018(10) 0.0528(6) Uani 1 1 d . . . . .
 H17 H 1.104260 0.964193 0.830921 0.063 Uiso 1 1 calc R . . . .
 C18 C 0.5016(4) 0.66376(13) 0.62177(8) 0.0376(4) Uani 1 1 d . . . . .
 C19 C 0.6051(4) 0.62012(16) 0.58551(9) 0.0472(5) Uani 1 1 d . . . . .
 H19 H 0.747957 0.601173 0.592659 0.057 Uiso 1 1 calc R . . . .
 C20 C 0.4950(5) 0.60503(18) 0.53887(10) 0.0558(6) Uani 1 1 d . . . . .
 H20 H 0.564266 0.575420 0.514672 0.067 Uiso 1 1 calc R . . . .
 C21 C 0.2813(5) 0.63344(18) 0.52732(10) 0.0542(6) Uani 1 1 d . . . . .
 C22 C 0.1827(4) 0.67717(17) 0.56403(11) 0.0523(6) Uani 1 1 d . . . . .
 H22 H 0.040577 0.696826 0.556817 0.063 Uiso 1 1 calc R . . . .
 C23 C 0.2900(4) 0.69247(15) 0.61127(9) 0.0454(5) Uani 1 1 d . . . . .
 H23 H 0.220591 0.721684 0.635609 0.055 Uiso 1 1 calc R . . . .
 C24 C 0.1594(7) 0.6160(3) 0.47653(13) 0.0856(11) Uani 1 1 d . . . . .
 H24A H 0.011085 0.635438 0.476582 0.128 Uiso 1 1 calc GR . . . .
 H24B H 0.158467 0.557755 0.470325 0.128 Uiso 1 1 calc GR . . . .
 H24C H 0.230869 0.643532 0.450344 0.128 Uiso 1 1 calc GR . . . .
 C25 C 0.5023(4) 0.44661(14) 0.75479(9) 0.0423(4) Uani 1 1 d . . . . .
 H25A H 0.410081 0.474419 0.729037 0.063 Uiso 1 1 calc GR . . . .
 H25B H 0.421259 0.436748 0.783774 0.063 Uiso 1 1 calc GR . . . .
 H25C H 0.549943 0.395100 0.741735 0.063 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
 Cl1 C26 1.749(5) . ?
 Cl2 C26 1.737(5) . ?
 Cl3 C26 1.713(5) . ?
 C26 H26 0.9800 . ?
 S1 O3 1.4355(18) . ?
 S1 O4 1.4363(17) . ?
 S1 N2 1.6169(19) . ?
 S1 C18 1.768(2) . ?
 F1 C7 1.397(2) . ?
 O1 C10 1.234(3) . ?
 O2 C12 1.370(3) . ?
 O2 C13 1.347(3) . ?
 N1 C5 1.411(3) . ?
 N1 C8 1.350(3) . ?
 N1 C25 1.451(3) . ?
 N2 C8 1.296(3) . ?
 C1 H1 0.9300 . ?
 C1 C2 1.412(4) . ?
 C1 C6 1.378(3) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.366(5) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.391(4) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.377(3) . ?
 C5 C6 1.383(3) . ?
 C6 C7 1.503(3) . ?
 C7 C8 1.560(3) . ?
 C7 C9 1.501(3) . ?
 C9 C10 1.449(3) . ?
 C9 C13 1.340(3) . ?
 C10 C11 1.467(3) . ?
 C11 C12 1.389(3) . ?
 C11 C14 1.397(3) . ?
 C12 C17 1.392(3) . ?
 C13 H13 0.9300 . ?
 C14 H14 0.9300 . ?
 C14 C15 1.381(4) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.381(5) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.368(4) . ?
 C17 H17 0.9300 . ?
 C18 C19 1.387(3) . ?
 C18 C23 1.381(3) . ?
 C19 H19 0.9300 . ?
 C19 C20 1.377(4) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.395(4) . ?
 C21 C22 1.381(4) . ?
 C21 C24 1.508(4) . ?
 C22 H22 0.9300 . ?
 C22 C23 1.384(4) . ?
 C23 H23 0.9300 . ?
 C24 H24A 0.9600 . ?
 C24 H24B 0.9600 . ?
 C24 H24C 0.9600 . ?
 C25 H25A 0.9600 . ?
 C25 H25B 0.9600 . ?
 C25 H25C 0.9600 . ?

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
 Cl1 C26 H26 108.4 . . ?
 Cl2 C26 Cl1 108.9(3) . . ?
 Cl2 C26 H26 108.4 . . ?
 Cl3 C26 Cl1 112.2(3) . . ?
 Cl3 C26 Cl2 110.5(3) . . ?
 Cl3 C26 H26 108.4 . . ?
 O3 S1 O4 117.60(12) . . ?
 O3 S1 N2 113.37(11) . . ?
 O3 S1 C18 107.13(11) . . ?
 O4 S1 N2 109.16(10) . . ?
 O4 S1 C18 108.29(11) . . ?
 N2 S1 C18 99.62(10) . . ?
 C13 O2 C12 118.72(18) . . ?
 C5 N1 C25 124.03(19) . . ?
 C8 N1 C5 111.52(18) . . ?
 C8 N1 C25 124.45(18) . . ?
 C8 N2 S1 125.05(16) . . ?
 C2 C1 H1 121.5 . . ?
 C6 C1 H1 121.5 . . ?
 C6 C1 C2 117.0(3) . . ?
 C1 C2 H2 119.6 . . ?
 C3 C2 C1 120.7(3) . . ?
 C3 C2 H2 119.6 . . ?
 C2 C3 H3 118.8 . . ?
 C2 C3 C4 122.4(3) . . ?
 C4 C3 H3 118.8 . . ?
 C3 C4 H4 121.8 . . ?
 C5 C4 C3 116.3(3) . . ?
 C5 C4 H4 121.8 . . ?
 C4 C5 N1 127.6(2) . . ?
 C4 C5 C6 122.4(2) . . ?
 C6 C5 N1 110.0(2) . . ?
 C1 C6 C5 121.2(2) . . ?
 C1 C6 C7 129.9(2) . . ?
 C5 C6 C7 108.80(19) . . ?
 F1 C7 C6 108.61(17) . . ?
 F1 C7 C8 106.66(16) . . ?
 F1 C7 C9 108.80(17) . . ?
 C6 C7 C8 101.89(17) . . ?
 C9 C7 C6 115.28(18) . . ?
 C9 C7 C8 115.05(17) . . ?
 N1 C8 C7 107.64(17) . . ?
 N2 C8 N1 120.78(19) . . ?
 N2 C8 C7 131.33(19) . . ?
 C10 C9 C7 118.61(18) . . ?
 C13 C9 C7 120.72(19) . . ?
 C13 C9 C10 120.7(2) . . ?
 O1 C10 C9 122.4(2) . . ?
 O1 C10 C11 123.06(19) . . ?
 C9 C10 C11 114.51(18) . . ?
 C12 C11 C10 120.01(19) . . ?
 C12 C11 C14 118.1(2) . . ?
 C14 C11 C10 121.9(2) . . ?
 O2 C12 C11 121.7(2) . . ?
 O2 C12 C17 116.5(2) . . ?
 C11 C12 C17 121.8(2) . . ?
 O2 C13 H13 117.8 . . ?
 C9 C13 O2 124.4(2) . . ?
 C9 C13 H13 117.8 . . ?
 C11 C14 H14 119.9 . . ?
 C15 C14 C11 120.2(3) . . ?
 C15 C14 H14 119.9 . . ?
 C14 C15 H15 119.8 . . ?
 C14 C15 C16 120.3(3) . . ?
 C16 C15 H15 119.8 . . ?
 C15 C16 H16 119.6 . . ?
 C17 C16 C15 120.9(2) . . ?
 C17 C16 H16 119.6 . . ?
 C12 C17 H17 120.7 . . ?
 C16 C17 C12 118.7(3) . . ?
 C16 C17 H17 120.7 . . ?
 C19 C18 S1 119.27(17) . . ?
 C23 C18 S1 120.23(17) . . ?
 C23 C18 C19 120.5(2) . . ?
 C18 C19 H19 120.2 . . ?
 C20 C19 C18 119.6(2) . . ?
 C20 C19 H19 120.2 . . ?
 C19 C20 H20 119.5 . . ?
 C19 C20 C21 121.1(2) . . ?
 C21 C20 H20 119.5 . . ?
 C20 C21 C24 121.1(3) . . ?
 C22 C21 C20 118.2(2) . . ?
 C22 C21 C24 120.7(3) . . ?
 C21 C22 H22 119.2 . . ?
 C21 C22 C23 121.7(2) . . ?
 C23 C22 H22 119.2 . . ?
 C18 C23 C22 119.1(2) . . ?
 C18 C23 H23 120.5 . . ?
 C22 C23 H23 120.5 . . ?
 C21 C24 H24A 109.5 . . ?
 C21 C24 H24B 109.5 . . ?
 C21 C24 H24C 109.5 . . ?
 H24A C24 H24B 109.5 . . ?
 H24A C24 H24C 109.5 . . ?
 H24B C24 H24C 109.5 . . ?
 N1 C25 H25A 109.5 . . ?
 N1 C25 H25B 109.5 . . ?
 N1 C25 H25C 109.5 . . ?
 H25A C25 H25B 109.5 . . ?
 H25A C25 H25C 109.5 . . ?
 H25B C25 H25C 109.5 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
