data_engle77_0m_a
_audit_creation_date              2018-02-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2016/6'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_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. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C20 H18 F N O2 S2'
_chemical_formula_sum             'C20 H18 F N O2 S2'
_chemical_formula_weight          387.47
_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' 0.0181 0.0091 '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' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S' 'S' 0.3331 0.5567 '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       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                    7.0055(2)
_cell_length_b                    10.2801(3)
_cell_length_c                    13.1310(3)
_cell_angle_alpha                 79.220(2)
_cell_angle_beta                  84.888(2)
_cell_angle_gamma                 80.238(2)
_cell_volume                      913.91(4)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     6173
_cell_measurement_temperature     200
_cell_measurement_theta_max       68.240
_cell_measurement_theta_min       4.434
_shelx_estimated_absorpt_T_max    0.513
_shelx_estimated_absorpt_T_min    0.492
_exptl_absorpt_coefficient_mu     2.851
_exptl_absorpt_correction_T_max   0.7531
_exptl_absorpt_correction_T_min   0.6344
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0683 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.8424. 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     1.408
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        block
_exptl_crystal_F_000              404
_exptl_crystal_size_max           0.29
_exptl_crystal_size_mid           0.28
_exptl_crystal_size_min           0.27
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0260
_diffrn_reflns_av_unetI/netI      0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_number             8744
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full         67.679
_diffrn_reflns_theta_max          68.311
_diffrn_reflns_theta_min          4.433
_diffrn_ambient_temperature       200
_diffrn_detector                  'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean  7.9
_diffrn_detector_type             'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device        'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_radiation_monochromator   'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe           X-ray
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54178
_diffrn_source                    'Micro Focus Rotating Anode'
_diffrn_source_type               'Bruker MicroStar FR-592'
_diffrn_standards_number          0
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 2940
_reflns_number_total              3247
_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        'APEX3 v2016.9-0 (Bruker, 2016)'
_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          0.365
_refine_diff_density_min          -0.381
_refine_diff_density_rms          0.046
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.043
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      237
_refine_ls_number_reflns          3247
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0410
_refine_ls_R_factor_gt            0.0371
_refine_ls_restrained_S_all       1.043
_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)+(0.0479P)²+0.4904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0969
_refine_ls_wR_factor_ref          0.1009
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C2(H2), C11(H11), C12(H12), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      ?
_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 0.99296(7) 0.16284(5) 0.88031(4) 0.03818(16) Uani 1 1 d . . . . .
 S2 S 0.68685(7) -0.00829(5) 0.90972(4) 0.03809(15) Uani 1 1 d . . . . .
 F1 F 1.31006(18) 0.59955(12) 0.94782(10) 0.0480(3) Uani 1 1 d . . . . .
 O2 O 0.29872(19) 0.65096(14) 0.59487(10) 0.0389(3) Uani 1 1 d . . . . .
 O1 O 0.42367(19) 0.43208(14) 0.61957(11) 0.0395(3) Uani 1 1 d . . . . .
 N1 N 0.7549(2) 0.14326(15) 0.73265(12) 0.0330(3) Uani 1 1 d . . . . .
 C7 C 0.8105(3) 0.10761(17) 0.82623(14) 0.0296(4) Uani 1 1 d . . . . .
 C16 C 0.7226(2) 0.49587(18) 0.72764(13) 0.0292(4) Uani 1 1 d . . . . .
 H16 H 0.722053 0.405251 0.721663 0.035 Uiso 1 1 calc R . . . .
 C9 C 1.0443(2) 0.42333(17) 0.80838(13) 0.0264(3) Uani 1 1 d . . . . .
 C1 C 0.6035(3) 0.07667(18) 0.72000(15) 0.0321(4) Uani 1 1 d . . . . .
 C14 C 1.1916(2) 0.44811(18) 0.86473(13) 0.0286(4) Uani 1 1 d . . . . .
 C6 C 0.5458(3) -0.01099(18) 0.80800(15) 0.0341(4) Uani 1 1 d . . . . .
 C17 C 0.5813(3) 0.58617(19) 0.68356(15) 0.0342(4) Uani 1 1 d . . . . .
 H17 H 0.577067 0.678292 0.686388 0.041 Uiso 1 1 calc R . . . .
 C8 C 1.0682(2) 0.28955(18) 0.77376(14) 0.0308(4) Uani 1 1 d . . . . .
 H8A H 1.205631 0.262400 0.751449 0.037 Uiso 1 1 calc R . . . .
 H8B H 0.988437 0.296819 0.713784 0.037 Uiso 1 1 calc R . . . .
 C10 C 0.8797(2) 0.52165(18) 0.78473(13) 0.0280(4) Uani 1 1 d . . . . .
 C15 C 1.3656(3) 0.3445(2) 0.89535(16) 0.0372(4) Uani 1 1 d . . . . .
 H15A H 1.322724 0.266364 0.940715 0.056 Uiso 1 1 calc GR . . . .
 H15B H 1.451854 0.382714 0.932343 0.056 Uiso 1 1 calc GR . . . .
 H15C H 1.435358 0.316844 0.832903 0.056 Uiso 1 1 calc GR . . . .
 C2 C 0.5093(3) 0.0912(2) 0.62825(16) 0.0420(5) Uani 1 1 d . . . . .
 H2 H 0.544432 0.151326 0.567976 0.050 Uiso 1 1 calc R . . . .
 C11 C 0.8677(3) 0.64425(19) 0.81811(15) 0.0344(4) Uani 1 1 d . . . . .
 H11 H 0.757371 0.710884 0.803149 0.041 Uiso 1 1 calc R . . . .
 C12 C 1.0123(3) 0.67076(19) 0.87227(15) 0.0371(4) Uani 1 1 d . . . . .
 H12 H 1.003517 0.754757 0.894057 0.045 Uiso 1 1 calc R . . . .
 C3 C 0.3635(3) 0.0160(2) 0.62730(18) 0.0470(5) Uani 1 1 d . . . . .
 H3 H 0.299478 0.023871 0.565137 0.056 Uiso 1 1 calc R . . . .
 C18 C 0.4309(2) 0.54464(19) 0.63026(14) 0.0316(4) Uani 1 1 d . . . . .
 C13 C 1.1696(3) 0.57227(19) 0.89386(14) 0.0327(4) Uani 1 1 d . . . . .
 C20 C -0.0036(3) 0.7468(3) 0.52240(19) 0.0547(6) Uani 1 1 d . . . . .
 H20A H 0.055776 0.819635 0.479211 0.082 Uiso 1 1 calc GR . . . .
 H20B H -0.051469 0.772409 0.589407 0.082 Uiso 1 1 calc GR . . . .
 H20C H -0.111961 0.729509 0.487208 0.082 Uiso 1 1 calc GR . . . .
 C5 C 0.3981(3) -0.0854(2) 0.80664(18) 0.0434(5) Uani 1 1 d . . . . .
 H5 H 0.360111 -0.144504 0.866877 0.052 Uiso 1 1 calc R . . . .
 C19 C 0.1446(3) 0.6225(2) 0.53979(16) 0.0426(5) Uani 1 1 d . . . . .
 H19A H 0.084979 0.547325 0.581248 0.051 Uiso 1 1 calc R . . . .
 H19B H 0.196874 0.597209 0.472444 0.051 Uiso 1 1 calc R . . . .
 C4 C 0.3089(3) -0.0707(2) 0.7152(2) 0.0480(5) Uani 1 1 d . . . . .
 H4 H 0.208026 -0.120780 0.712175 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 C7 1.7375(18) . ?
 S1 C8 1.8307(19) . ?
 S2 C7 1.7505(19) . ?
 S2 C6 1.738(2) . ?
 F1 C13 1.357(2) . ?
 O2 C18 1.346(2) . ?
 O2 C19 1.449(2) . ?
 O1 C18 1.201(2) . ?
 N1 C7 1.290(2) . ?
 N1 C1 1.393(2) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.329(3) . ?
 C16 C10 1.471(2) . ?
 C9 C14 1.404(2) . ?
 C9 C8 1.506(2) . ?
 C9 C10 1.414(2) . ?
 C1 C6 1.401(3) . ?
 C1 C2 1.396(3) . ?
 C14 C15 1.507(2) . ?
 C14 C13 1.380(3) . ?
 C6 C5 1.391(3) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.476(2) . ?
 C8 H8A 0.9900 . ?
 C8 H8B 0.9900 . ?
 C10 C11 1.397(3) . ?
 C15 H15A 0.9800 . ?
 C15 H15B 0.9800 . ?
 C15 H15C 0.9800 . ?
 C2 H2 0.9500 . ?
 C2 C3 1.384(3) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.379(3) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.375(3) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.388(3) . ?
 C20 H20A 0.9800 . ?
 C20 H20B 0.9800 . ?
 C20 H20C 0.9800 . ?
 C20 C19 1.498(3) . ?
 C5 H5 0.9500 . ?
 C5 C4 1.374(3) . ?
 C19 H19A 0.9900 . ?
 C19 H19B 0.9900 . ?
 C4 H4 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
 C7 S1 C8 101.81(8) . . ?
 C6 S2 C7 88.63(9) . . ?
 C18 O2 C19 115.66(15) . . ?
 C7 N1 C1 109.96(16) . . ?
 S1 C7 S2 115.69(10) . . ?
 N1 C7 S1 127.58(14) . . ?
 N1 C7 S2 116.72(14) . . ?
 C17 C16 H16 116.6 . . ?
 C17 C16 C10 126.76(17) . . ?
 C10 C16 H16 116.6 . . ?
 C14 C9 C8 117.91(15) . . ?
 C14 C9 C10 120.72(16) . . ?
 C10 C9 C8 121.36(15) . . ?
 N1 C1 C6 115.48(16) . . ?
 N1 C1 C2 125.15(18) . . ?
 C2 C1 C6 119.37(18) . . ?
 C9 C14 C15 122.57(16) . . ?
 C13 C14 C9 117.20(16) . . ?
 C13 C14 C15 120.22(16) . . ?
 C1 C6 S2 109.20(14) . . ?
 C5 C6 S2 128.88(17) . . ?
 C5 C6 C1 121.92(19) . . ?
 C16 C17 H17 119.7 . . ?
 C16 C17 C18 120.59(17) . . ?
 C18 C17 H17 119.7 . . ?
 S1 C8 H8A 109.6 . . ?
 S1 C8 H8B 109.6 . . ?
 C9 C8 S1 110.07(12) . . ?
 C9 C8 H8A 109.6 . . ?
 C9 C8 H8B 109.6 . . ?
 H8A C8 H8B 108.2 . . ?
 C9 C10 C16 121.23(16) . . ?
 C11 C10 C16 120.31(16) . . ?
 C11 C10 C9 118.45(16) . . ?
 C14 C15 H15A 109.5 . . ?
 C14 C15 H15B 109.5 . . ?
 C14 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 C1 C2 H2 120.8 . . ?
 C3 C2 C1 118.4(2) . . ?
 C3 C2 H2 120.8 . . ?
 C10 C11 H11 119.2 . . ?
 C12 C11 C10 121.51(17) . . ?
 C12 C11 H11 119.2 . . ?
 C11 C12 H12 120.9 . . ?
 C13 C12 C11 118.15(17) . . ?
 C13 C12 H12 120.9 . . ?
 C2 C3 H3 119.3 . . ?
 C2 C3 C4 121.4(2) . . ?
 C4 C3 H3 119.3 . . ?
 O2 C18 C17 110.68(16) . . ?
 O1 C18 O2 123.58(16) . . ?
 O1 C18 C17 125.73(16) . . ?
 F1 C13 C14 118.59(16) . . ?
 F1 C13 C12 117.45(16) . . ?
 C12 C13 C14 123.96(16) . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 109.5 . . ?
 C19 C20 H20A 109.5 . . ?
 C19 C20 H20B 109.5 . . ?
 C19 C20 H20C 109.5 . . ?
 C6 C5 H5 121.1 . . ?
 C4 C5 C6 117.7(2) . . ?
 C4 C5 H5 121.1 . . ?
 O2 C19 C20 107.67(18) . . ?
 O2 C19 H19A 110.2 . . ?
 O2 C19 H19B 110.2 . . ?
 C20 C19 H19A 110.2 . . ?
 C20 C19 H19B 110.2 . . ?
 H19A C19 H19B 108.5 . . ?
 C3 C4 H4 119.4 . . ?
 C5 C4 C3 121.22(19) . . ?
 C5 C4 H4 119.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
