# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mmc_07_078a3_0m
_database_code_depnum_ccdc_archive 'CCDC 1999111'
loop_
_audit_author_name
_audit_author_address
'Nobuyuki Yamamoto'
;San Diego State University
United States of America
;
_audit_update_record             
;
2020-04-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2020-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
''
''
''
nyamamoto2@sdsu.edu
''
''
_chemical_name_common            ?
_chemical_name_systematic        
3-([1,1'-biphenyl]-2-yl)-4-methyl-2-(phenylthio)quinoline
_chemical_formula_moiety         'C28 H21 N S'
_chemical_formula_sum            'C28 H21 N S'
_chemical_formula_weight         403.52
_chemical_absolute_configuration ?
_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'
N N 0.0061 0.0033 '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                   10.0555(4)
_cell_length_b                   11.6803(5)
_cell_length_c                   18.1925(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.9539(18)
_cell_angle_gamma                90
_cell_volume                     2097.80(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.28
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.8943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0478 before and 0.0399 after correction. The Ratio of minimum to maximum transmission is 0.9215. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            42835
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         1.140
_diffrn_ambient_temperature      100
_diffrn_detector                 MoK\a
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            graphite
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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         0.906
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                9069
_reflns_number_total             9235
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         9235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.171
_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)+(0.0326P)²+1.1925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.95(7)
 0.05(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C7(H7), C25(H25), C27(H27), C6(H6), C9(H9), C17(H17),
 C15(H15), C21(H21), C20(H20), C26(H26), C29(H29), C23(H23), C28(H28), C16(H16),
  C22(H22), C19(H19), C36(H36), C45(H45), C37(H37), C53(H53), C43(H43),
 C51(H51), C35(H35), C42(H42), C34(H34), C49(H49), C50(H50), C54(H54), C56(H56),
  C57(H57), C55(H55), C48(H48), C44(H44), C47(H47)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.65850(7) 0.72914(6) 0.40009(4) 0.02028(15) Uani 1 1 d . . . . .
N1 N 0.9100(2) 0.7438(2) 0.37108(13) 0.0168(5) Uani 1 1 d . . . . .
C24 C 0.6828(3) 0.8796(3) 0.39942(16) 0.0172(5) Uani 1 1 d . . . . .
C2 C 0.8150(3) 0.6734(2) 0.38307(15) 0.0155(5) Uani 1 1 d . . . . .
C8 C 1.2542(3) 0.7264(3) 0.33502(16) 0.0212(6) Uani 1 1 d . . . . .
H8 H 1.326295 0.777055 0.330824 0.025 Uiso 1 1 calc R . . . .
C14 C 0.5618(3) 0.4036(2) 0.47632(15) 0.0182(5) Uani 1 1 d . . . . .
H14 H 0.542049 0.392465 0.524835 0.022 Uiso 1 1 calc R . . . .
C13 C 0.6757(3) 0.4685(2) 0.46876(15) 0.0156(5) Uani 1 1 d . . . . .
C7 C 1.2721(3) 0.6073(3) 0.32859(16) 0.0227(6) Uani 1 1 d . . . . .
H7 H 1.355690 0.578094 0.319606 0.027 Uiso 1 1 calc R . . . .
C3 C 0.8233(3) 0.5506(2) 0.38217(14) 0.0153(5) Uani 1 1 d . . . . .
C25 C 0.7514(3) 0.9364(3) 0.46281(16) 0.0207(6) Uani 1 1 d . . . . .
H25 H 0.796163 0.893819 0.504790 0.025 Uiso 1 1 calc R . . . .
C10 C 1.0265(3) 0.6952(2) 0.35616(15) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.9367(3) 0.5017(2) 0.36352(14) 0.0149(5) Uani 1 1 d . . . . .
C5 C 1.0443(3) 0.5754(2) 0.35066(15) 0.0161(5) Uani 1 1 d . . . . .
C27 C 0.6898(3) 1.1171(3) 0.40364(19) 0.0247(6) Uani 1 1 d . . . . .
H27 H 0.692106 1.198375 0.405063 0.030 Uiso 1 1 calc R . . . .
C6 C 1.1687(3) 0.5334(3) 0.33531(16) 0.0193(6) Uani 1 1 d . . . . .
H6 H 1.180602 0.453466 0.329633 0.023 Uiso 1 1 calc R . . . .
C9 C 1.1330(3) 0.7698(3) 0.34733(16) 0.0190(6) Uani 1 1 d . . . . .
H9 H 1.120998 0.850314 0.349895 0.023 Uiso 1 1 calc R . . . .
C17 C 0.6201(3) 0.4319(3) 0.33518(15) 0.0187(6) Uani 1 1 d . . . . .
H17 H 0.640016 0.441000 0.286521 0.022 Uiso 1 1 calc R . . . .
C18 C 0.7550(3) 0.5226(2) 0.53776(15) 0.0153(5) Uani 1 1 d . . . . .
C12 C 0.7056(3) 0.4815(2) 0.39668(15) 0.0159(5) Uani 1 1 d . . . . .
C15 C 0.4774(3) 0.3554(3) 0.41529(17) 0.0204(6) Uani 1 1 d . . . . .
H15 H 0.399996 0.312873 0.421965 0.025 Uiso 1 1 calc R . . . .
C21 C 0.8915(3) 0.6122(3) 0.67518(16) 0.0223(6) Uani 1 1 d . . . . .
H21 H 0.937751 0.641401 0.721812 0.027 Uiso 1 1 calc R . . . .
C11 C 0.9504(3) 0.3731(2) 0.35736(17) 0.0208(6) Uani 1 1 d . . . . .
H11A H 0.877334 0.335496 0.377003 0.031 Uiso 1 1 calc GR . . . .
H11B H 1.038081 0.348763 0.386374 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.944578 0.351965 0.304725 0.031 Uiso 1 1 calc GR . . . .
C20 C 0.7512(3) 0.6140(3) 0.65711(16) 0.0242(6) Uani 1 1 d . . . . .
H20 H 0.700770 0.645691 0.691356 0.029 Uiso 1 1 calc R . . . .
C26 C 0.7543(3) 1.0550(3) 0.46449(17) 0.0240(6) Uani 1 1 d . . . . .
H26 H 0.800898 1.093629 0.507752 0.029 Uiso 1 1 calc R . . . .
C29 C 0.6175(3) 0.9422(3) 0.33835(16) 0.0227(6) Uani 1 1 d . . . . .
H29 H 0.570012 0.903953 0.295136 0.027 Uiso 1 1 calc R . . . .
C23 C 0.8965(3) 0.5221(2) 0.55588(16) 0.0194(6) Uani 1 1 d . . . . .
H23 H 0.947268 0.491043 0.521580 0.023 Uiso 1 1 calc R . . . .
C28 C 0.6220(3) 1.0615(3) 0.34070(18) 0.0248(6) Uani 1 1 d . . . . .
H28 H 0.578152 1.104595 0.298760 0.030 Uiso 1 1 calc R . . . .
C16 C 0.5065(3) 0.3694(3) 0.34420(17) 0.0206(6) Uani 1 1 d . . . . .
H16 H 0.449120 0.336480 0.301953 0.025 Uiso 1 1 calc R . . . .
C22 C 0.9634(3) 0.5667(3) 0.62373(17) 0.0221(6) Uani 1 1 d . . . . .
H22 H 1.059602 0.566081 0.635166 0.027 Uiso 1 1 calc R . . . .
C19 C 0.6842(3) 0.5700(3) 0.58969(17) 0.0217(6) Uani 1 1 d . . . . .
H19 H 0.588032 0.572062 0.578286 0.026 Uiso 1 1 calc R . . . .
S2 S 0.74118(7) 0.31252(6) 0.12346(5) 0.02357(17) Uani 1 1 d . . . . .
C52 C 0.7676(3) 0.1616(2) 0.12210(17) 0.0179(6) Uani 1 1 d . . . . .
N2 N 1.0109(2) 0.2979(2) 0.13794(13) 0.0182(5) Uani 1 1 d . . . . .
C30 C 0.9080(3) 0.3675(2) 0.12986(16) 0.0170(5) Uani 1 1 d . . . . .
C32 C 1.0439(3) 0.5388(2) 0.13411(15) 0.0166(5) Uani 1 1 d . . . . .
C41 C 0.7049(3) 0.5787(2) 0.04722(16) 0.0169(5) Uani 1 1 d . . . . .
C33 C 1.1589(3) 0.4647(2) 0.14158(14) 0.0157(5) Uani 1 1 d . . . . .
C40 C 0.7907(3) 0.5604(2) 0.11721(15) 0.0156(5) Uani 1 1 d . . . . .
C31 C 0.9164(3) 0.4901(2) 0.12649(14) 0.0150(5) Uani 1 1 d . . . . .
C36 C 1.3765(3) 0.3115(3) 0.14880(16) 0.0214(6) Uani 1 1 d . . . . .
H36 H 1.450052 0.260034 0.150219 0.026 Uiso 1 1 calc R . . . .
C38 C 1.1367(3) 0.3445(2) 0.14246(15) 0.0162(5) Uani 1 1 d . . . . .
C39 C 1.0619(3) 0.6667(2) 0.13248(18) 0.0219(6) Uani 1 1 d . . . . .
H39A H 1.116507 0.692204 0.180128 0.033 Uiso 1 1 calc GR . . . .
H39B H 0.973040 0.703972 0.124812 0.033 Uiso 1 1 calc GR . . . .
H39C H 1.107982 0.687198 0.091447 0.033 Uiso 1 1 calc GR . . . .
C45 C 0.7564(3) 0.6084(2) 0.18154(15) 0.0183(6) Uani 1 1 d . . . . .
H45 H 0.814323 0.596079 0.228578 0.022 Uiso 1 1 calc R . . . .
C37 C 1.2488(3) 0.2697(3) 0.14736(16) 0.0192(6) Uani 1 1 d . . . . .
H37 H 1.235220 0.189413 0.149676 0.023 Uiso 1 1 calc R . . . .
C53 C 0.7580(3) 0.1047(3) 0.05429(16) 0.0227(6) Uani 1 1 d . . . . .
H53 H 0.746200 0.146896 0.008869 0.027 Uiso 1 1 calc R . . . .
C43 C 0.5567(3) 0.6938(2) 0.10966(18) 0.0217(6) Uani 1 1 d . . . . .
H43 H 0.477498 0.739226 0.106643 0.026 Uiso 1 1 calc R . . . .
C51 C 0.8540(3) 0.5236(3) -0.04510(16) 0.0222(6) Uani 1 1 d . . . . .
H51 H 0.931711 0.550990 -0.011643 0.027 Uiso 1 1 calc R . . . .
C46 C 0.7279(3) 0.5276(2) -0.02408(15) 0.0184(5) Uani 1 1 d . . . . .
C35 C 1.3994(3) 0.4308(3) 0.14818(15) 0.0203(6) Uani 1 1 d . . . . .
H35 H 1.488180 0.459405 0.149193 0.024 Uiso 1 1 calc R . . . .
C42 C 0.5895(3) 0.6471(3) 0.04539(16) 0.0200(6) Uani 1 1 d . . . . .
H42 H 0.532101 0.661904 -0.001447 0.024 Uiso 1 1 calc R . . . .
C34 C 1.2936(3) 0.5052(2) 0.14612(15) 0.0185(6) Uani 1 1 d . . . . .
H34 H 1.310454 0.585236 0.147749 0.022 Uiso 1 1 calc R . . . .
C49 C 0.7561(4) 0.4415(3) -0.16456(17) 0.0307(7) Uani 1 1 d . . . . .
H49 H 0.765706 0.412327 -0.212020 0.037 Uiso 1 1 calc R . . . .
C50 C 0.8675(3) 0.4802(3) -0.11439(18) 0.0287(7) Uani 1 1 d . . . . .
H50 H 0.954599 0.477002 -0.127384 0.034 Uiso 1 1 calc R . . . .
C54 C 0.7657(3) -0.0139(3) 0.05299(17) 0.0245(6) Uani 1 1 d . . . . .
H54 H 0.758612 -0.053018 0.006628 0.029 Uiso 1 1 calc R . . . .
C56 C 0.7945(3) -0.0191(3) 0.18699(18) 0.0249(6) Uani 1 1 d . . . . .
H56 H 0.807923 -0.061506 0.232366 0.030 Uiso 1 1 calc R . . . .
C57 C 0.7856(3) 0.1003(3) 0.18864(17) 0.0231(6) Uani 1 1 d . . . . .
H57 H 0.791935 0.139318 0.235009 0.028 Uiso 1 1 calc R . . . .
C55 C 0.7837(3) -0.0753(3) 0.11941(18) 0.0240(6) Uani 1 1 d . . . . .
H55 H 0.788602 -0.156515 0.118352 0.029 Uiso 1 1 calc R . . . .
C48 C 0.6299(4) 0.4459(3) -0.14456(18) 0.0325(8) Uani 1 1 d . . . . .
H48 H 0.552236 0.420274 -0.178830 0.039 Uiso 1 1 calc R . . . .
C44 C 0.6400(3) 0.6737(2) 0.17846(17) 0.0216(6) Uani 1 1 d . . . . .
H44 H 0.617743 0.704268 0.222972 0.026 Uiso 1 1 calc R . . . .
C47 C 0.6157(3) 0.4874(3) -0.07497(17) 0.0260(6) Uani 1 1 d . . . . .
H47 H 0.528759 0.488528 -0.061785 0.031 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 C24 1.775(3) . ?
S1 C2 1.784(3) . ?
N1 C2 1.310(4) . ?
N1 C10 1.374(3) . ?
C24 C25 1.394(4) . ?
C24 C29 1.386(4) . ?
C2 C3 1.437(4) . ?
C8 C7 1.411(5) . ?
C8 C9 1.376(4) . ?
C14 C13 1.401(4) . ?
C14 C15 1.383(4) . ?
C13 C18 1.493(4) . ?
C13 C12 1.408(4) . ?
C7 C6 1.374(4) . ?
C3 C4 1.375(4) . ?
C3 C12 1.496(4) . ?
C25 C26 1.386(4) . ?
C10 C5 1.417(4) . ?
C10 C9 1.414(4) . ?
C4 C5 1.436(4) . ?
C4 C11 1.513(4) . ?
C5 C6 1.420(4) . ?
C27 C26 1.378(5) . ?
C27 C28 1.379(5) . ?
C17 C12 1.401(4) . ?
C17 C16 1.392(4) . ?
C18 C23 1.399(4) . ?
C18 C19 1.401(4) . ?
C15 C16 1.389(4) . ?
C21 C20 1.387(4) . ?
C21 C22 1.392(4) . ?
C20 C19 1.381(4) . ?
C29 C28 1.395(5) . ?
C23 C22 1.390(4) . ?
S2 C52 1.784(3) . ?
S2 C30 1.779(3) . ?
C52 C53 1.388(4) . ?
C52 C57 1.388(4) . ?
N2 C30 1.302(4) . ?
N2 C38 1.365(4) . ?
C30 C31 1.437(4) . ?
C32 C33 1.430(4) . ?
C32 C31 1.385(4) . ?
C32 C39 1.506(4) . ?
C41 C40 1.412(4) . ?
C41 C46 1.485(4) . ?
C41 C42 1.404(4) . ?
C33 C38 1.422(4) . ?
C33 C34 1.423(4) . ?
C40 C31 1.490(4) . ?
C40 C45 1.398(4) . ?
C36 C37 1.370(4) . ?
C36 C35 1.413(5) . ?
C38 C37 1.415(4) . ?
C45 C44 1.389(4) . ?
C53 C54 1.388(4) . ?
C43 C42 1.386(4) . ?
C43 C44 1.388(4) . ?
C51 C46 1.393(4) . ?
C51 C50 1.389(4) . ?
C46 C47 1.397(4) . ?
C35 C34 1.368(4) . ?
C49 C50 1.380(5) . ?
C49 C48 1.386(5) . ?
C54 C55 1.387(4) . ?
C56 C57 1.399(4) . ?
C56 C55 1.380(5) . ?
C48 C47 1.388(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
C24 S1 C2 103.49(13) . . ?
C2 N1 C10 116.7(2) . . ?
C25 C24 S1 120.8(2) . . ?
C29 C24 S1 118.8(2) . . ?
C29 C24 C25 119.8(3) . . ?
N1 C2 S1 119.7(2) . . ?
N1 C2 C3 125.4(2) . . ?
C3 C2 S1 114.9(2) . . ?
C9 C8 C7 120.5(3) . . ?
C15 C14 C13 122.0(3) . . ?
C14 C13 C18 117.5(2) . . ?
C14 C13 C12 118.2(2) . . ?
C12 C13 C18 124.2(2) . . ?
C6 C7 C8 120.1(3) . . ?
C2 C3 C12 119.1(2) . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 C12 122.7(2) . . ?
C26 C25 C24 119.9(3) . . ?
N1 C10 C5 123.0(2) . . ?
N1 C10 C9 117.5(2) . . ?
C9 C10 C5 119.5(2) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C11 121.4(2) . . ?
C5 C4 C11 120.1(2) . . ?
C10 C5 C4 118.2(2) . . ?
C10 C5 C6 118.8(3) . . ?
C6 C5 C4 123.0(3) . . ?
C26 C27 C28 120.1(3) . . ?
C7 C6 C5 120.7(3) . . ?
C8 C9 C10 120.3(3) . . ?
C16 C17 C12 121.1(3) . . ?
C23 C18 C13 123.6(2) . . ?
C23 C18 C19 117.9(3) . . ?
C19 C18 C13 118.4(2) . . ?
C13 C12 C3 122.6(2) . . ?
C17 C12 C13 119.4(3) . . ?
C17 C12 C3 117.9(2) . . ?
C14 C15 C16 119.6(3) . . ?
C20 C21 C22 118.8(3) . . ?
C19 C20 C21 120.5(3) . . ?
C27 C26 C25 120.2(3) . . ?
C24 C29 C28 119.6(3) . . ?
C22 C23 C18 120.5(3) . . ?
C27 C28 C29 120.3(3) . . ?
C15 C16 C17 119.6(3) . . ?
C23 C22 C21 121.0(3) . . ?
C20 C19 C18 121.4(3) . . ?
C30 S2 C52 102.52(13) . . ?
C53 C52 S2 120.0(2) . . ?
C57 C52 S2 119.5(2) . . ?
C57 C52 C53 120.3(3) . . ?
C30 N2 C38 117.8(2) . . ?
N2 C30 S2 120.1(2) . . ?
N2 C30 C31 125.1(3) . . ?
C31 C30 S2 114.8(2) . . ?
C33 C32 C39 120.3(2) . . ?
C31 C32 C33 118.5(3) . . ?
C31 C32 C39 121.2(2) . . ?
C40 C41 C46 123.9(2) . . ?
C42 C41 C40 117.9(3) . . ?
C42 C41 C46 118.2(2) . . ?
C38 C33 C32 118.2(2) . . ?
C38 C33 C34 118.5(3) . . ?
C34 C33 C32 123.2(3) . . ?
C41 C40 C31 123.0(2) . . ?
C45 C40 C41 119.3(2) . . ?
C45 C40 C31 117.7(2) . . ?
C30 C31 C40 119.9(2) . . ?
C32 C31 C30 117.8(2) . . ?
C32 C31 C40 122.3(2) . . ?
C37 C36 C35 120.4(3) . . ?
N2 C38 C33 122.6(2) . . ?
N2 C38 C37 118.4(2) . . ?
C37 C38 C33 119.0(3) . . ?
C44 C45 C40 121.7(3) . . ?
C36 C37 C38 120.9(3) . . ?
C52 C53 C54 119.9(3) . . ?
C42 C43 C44 119.7(3) . . ?
C50 C51 C46 120.8(3) . . ?
C51 C46 C41 123.6(3) . . ?
C51 C46 C47 118.0(3) . . ?
C47 C46 C41 118.3(3) . . ?
C34 C35 C36 119.9(3) . . ?
C43 C42 C41 122.2(3) . . ?
C35 C34 C33 121.2(3) . . ?
C50 C49 C48 118.9(3) . . ?
C49 C50 C51 120.8(3) . . ?
C55 C54 C53 120.0(3) . . ?
C55 C56 C57 119.9(3) . . ?
C52 C57 C56 119.6(3) . . ?
C56 C55 C54 120.3(3) . . ?
C49 C48 C47 120.7(3) . . ?
C43 C44 C45 119.3(3) . . ?
C48 C47 C46 120.8(3) . . ?

_olex2_date_sample_completion    2020-01-20
_olex2_date_sample_data_collection 2020-01-14
_olex2_date_sample_submission    2020-01-14
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.95(7)
2 0.05(7)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mmc_07_124a_0m
_database_code_depnum_ccdc_archive 'CCDC 1999112'
loop_
_audit_author_name
_audit_author_address
'Nobuyuki Yamamoto'
;San Diego State University
United States of America
;
_audit_update_record             
;
2020-04-25 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2020-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
''
''
''
nyamamoto2@sdsu.edu
''
''
_chemical_name_common            ?
_chemical_name_systematic        
3-(2-fluoro-5-(trifluoromethyl)phenyl)-4-methyl-2-(phenylthio)quinoline
_chemical_formula_moiety         'C23 H15 F4 N S'
_chemical_formula_sum            'C23 H15 F4 N S'
_chemical_formula_weight         413.42
_chemical_absolute_configuration ad
_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'
N N 0.0061 0.0033 '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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.8999(2)
_cell_length_b                   13.7881(3)
_cell_length_c                   27.3121(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3728.12(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9999
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.85
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9282
_exptl_absorpt_correction_T_min  0.8450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0662 before and 0.0612 after correction. The Ratio of minimum to maximum transmission is 0.9104. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            86653
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.940
_diffrn_ambient_temperature      100
_diffrn_detector                 MoK\a
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            graphite
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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         0.790
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                8110
_reflns_number_total             8217
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         8217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0223
_refine_ls_restrained_S_all      1.058
_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)+(0.0329P)²+0.8626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0594
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.03(4)
 -0.03(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Sof(F7A)=1-FVAR(1)
 Sof(F7)=FVAR(1)
 Sof(F6A)=1-FVAR(2)
 Sof(F6)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C40(H40), C29(H29), C47(H47), C22(H22), C6(H6), C7(H7), C37(H37), C31(H31),
 C15(H15), C8(H8), C38(H38), C17(H17), C46(H46), C30(H30), C20(H20), C24(H24),
 C14(H14), C43(H43), C44(H44), C23(H23), C32(H32), C45(H45), C21(H21), C9(H9)
4.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.12474(4) 0.61144(3) 0.07203(2) 0.01854(9) Uani 1 1 d . . . . .
S2 S 0.46685(5) 0.43536(3) 0.11282(2) 0.01921(9) Uani 1 1 d . . . . .
F8 F 0.07725(11) 0.69907(8) 0.18832(4) 0.0258(2) Uani 1 1 d . . . . .
F5 F 0.54827(11) 0.41824(7) 0.24385(4) 0.0244(2) Uani 1 1 d . . . . .
F1 F 0.24747(12) 0.80539(8) -0.02927(4) 0.0283(2) Uani 1 1 d . . . . .
F3 F 0.54689(13) 0.81947(10) 0.17079(4) 0.0349(3) Uani 1 1 d . . . . .
F2 F 0.71267(11) 0.79328(10) 0.12222(4) 0.0319(3) Uani 1 1 d . . . . .
F4 F 0.59575(13) 0.67394(9) 0.14943(4) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.13951(14) 0.48535(10) -0.00277(5) 0.0157(3) Uani 1 1 d . . . . .
C25 C 0.37688(16) 0.34277(11) 0.14399(5) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.36646(14) 0.25569(9) 0.12544(5) 0.0152(3) Uani 1 1 d . . . . .
C19 C 0.01701(17) 0.52235(12) 0.09777(5) 0.0165(3) Uani 1 1 d . . . . .
C12 C 0.36026(16) 0.70082(12) 0.02517(6) 0.0160(3) Uani 1 1 d . . . . .
C40 C 0.25879(16) 0.54962(11) 0.19885(6) 0.0151(3) Uani 1 1 d . . . . .
H40 H 0.178901 0.539482 0.180268 0.018 Uiso 1 1 calc R . . . .
C4 C 0.36548(17) 0.58228(12) -0.04456(6) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.19419(16) 0.56150(11) 0.01758(5) 0.0148(3) Uani 1 1 d . . . . .
C29 C 0.15351(18) 0.13668(12) 0.22024(6) 0.0202(3) Uani 1 1 d . . . . .
H29 H 0.104912 0.151152 0.249327 0.024 Uiso 1 1 calc R . . . .
C42 C 0.51828(17) 0.38266(11) 0.05664(5) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.30576(16) 0.50067(11) -0.06880(6) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.19387(17) 0.45414(11) -0.04640(6) 0.0155(3) Uani 1 1 d . . . . .
C35 C 0.34549(16) 0.47225(11) 0.20817(5) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.30831(16) 0.61384(11) -0.00140(6) 0.0153(3) Uani 1 1 d . . . . .
C47 C 0.42652(17) 0.34025(12) 0.02440(6) 0.0181(3) Uani 1 1 d . . . . .
H47 H 0.333951 0.334780 0.033147 0.022 Uiso 1 1 calc R . . . .
C22 C -0.1392(2) 0.39846(14) 0.15488(6) 0.0249(4) Uani 1 1 d . . . . .
H22 H -0.191828 0.356178 0.174645 0.030 Uiso 1 1 calc R . . . .
C6 C 0.35364(18) 0.46439(12) -0.11428(6) 0.0201(3) Uani 1 1 d . . . . .
H6 H 0.429014 0.494390 -0.129585 0.024 Uiso 1 1 calc R . . . .
C28 C 0.22699(16) 0.21107(12) 0.19610(6) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.29247(19) 0.38661(14) -0.13639(6) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.325085 0.363523 -0.166959 0.027 Uiso 1 1 calc R . . . .
C37 C 0.49037(18) 0.58159(12) 0.25464(6) 0.0203(3) Uani 1 1 d . . . . .
H37 H 0.568947 0.591159 0.274007 0.024 Uiso 1 1 calc R . . . .
C31 C 0.22222(19) 0.02118(12) 0.15847(7) 0.0220(4) Uani 1 1 d . . . . .
H31 H 0.221845 -0.043390 0.146343 0.026 Uiso 1 1 calc R . . . .
C15 C 0.45810(18) 0.86675(11) 0.07371(6) 0.0202(3) Uani 1 1 d . . . . .
H15 H 0.491425 0.922428 0.090268 0.024 Uiso 1 1 calc R . . . .
C26 C 0.31857(16) 0.37224(11) 0.18976(5) 0.0133(3) Uani 1 1 d . . . . .
F7 F 0.2477(9) 0.7750(5) 0.1628(2) 0.0305(18) Uani 0.63(7) 1 d . . P A 1
F6 F 0.1870(8) 0.7921(5) 0.2366(5) 0.0344(18) Uani 0.63(6) 1 d . . P A 1
C8 C 0.18125(19) 0.34081(12) -0.11386(6) 0.0211(3) Uani 1 1 d . . . . .
H8 H 0.139168 0.287048 -0.129364 0.025 Uiso 1 1 calc R . . . .
C38 C 0.40335(18) 0.65780(12) 0.24496(6) 0.0192(3) Uani 1 1 d . . . . .
H38 H 0.421784 0.720633 0.257571 0.023 Uiso 1 1 calc R . . . .
C36 C 0.46060(17) 0.49152(11) 0.23558(6) 0.0166(3) Uani 1 1 d . . . . .
C17 C 0.44478(17) 0.69237(11) 0.06603(6) 0.0170(3) Uani 1 1 d . . . . .
H17 H 0.469601 0.629878 0.077596 0.020 Uiso 1 1 calc R . . . .
C18 C 0.58579(18) 0.76501(13) 0.13274(6) 0.0217(3) Uani 1 1 d . . . . .
C46 C 0.47141(19) 0.30595(12) -0.02070(6) 0.0204(3) Uani 1 1 d . . . . .
H46 H 0.409823 0.275497 -0.042494 0.025 Uiso 1 1 calc R . . . .
C27 C 0.24036(16) 0.30750(11) 0.21538(6) 0.0142(3) Uani 1 1 d . . . . .
C11 C 0.48867(18) 0.63003(13) -0.06602(6) 0.0230(4) Uani 1 1 d . . . . .
H11A H 0.561965 0.582495 -0.068413 0.035 Uiso 1 1 calc GR . . . .
H11B H 0.516968 0.683786 -0.044908 0.035 Uiso 1 1 calc GR . . . .
H11C H 0.467299 0.654918 -0.098730 0.035 Uiso 1 1 calc GR . . . .
C30 C 0.15214(18) 0.04372(13) 0.20182(7) 0.0229(4) Uani 1 1 d . . . . .
H30 H 0.103463 -0.005603 0.218510 0.028 Uiso 1 1 calc R . . . .
C20 C -0.09471(17) 0.55816(13) 0.12303(6) 0.0201(3) Uani 1 1 d . . . . .
H20 H -0.118382 0.624735 0.120424 0.024 Uiso 1 1 calc R . . . .
C24 C 0.04931(17) 0.42395(12) 0.10030(6) 0.0192(3) Uani 1 1 d . . . . .
H24 H 0.124639 0.399120 0.082774 0.023 Uiso 1 1 calc R . . . .
C14 C 0.37462(19) 0.87703(12) 0.03332(7) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.350011 0.939500 0.021663 0.027 Uiso 1 1 calc R . . . .
C43 C 0.65406(18) 0.39329(12) 0.04346(6) 0.0200(3) Uani 1 1 d . . . . .
H43 H 0.716207 0.422792 0.065382 0.024 Uiso 1 1 calc R . . . .
C33 C 0.29478(16) 0.18842(11) 0.15185(6) 0.0146(3) Uani 1 1 d . . . . .
C44 C 0.69716(19) 0.36021(13) -0.00207(6) 0.0222(3) Uani 1 1 d . . . . .
H44 H 0.788973 0.367703 -0.011448 0.027 Uiso 1 1 calc R . . . .
C23 C -0.02989(19) 0.36263(13) 0.12873(6) 0.0226(3) Uani 1 1 d . . . . .
H23 H -0.008939 0.295466 0.130278 0.027 Uiso 1 1 calc R . . . .
C32 C 0.29104(17) 0.09211(11) 0.13370(6) 0.0184(3) Uani 1 1 d . . . . .
H32 H 0.336636 0.076611 0.104110 0.022 Uiso 1 1 calc R . . . .
C16 C 0.49273(17) 0.77448(12) 0.08984(6) 0.0173(3) Uani 1 1 d . . . . .
C13 C 0.32805(17) 0.79411(12) 0.01040(6) 0.0189(3) Uani 1 1 d . . . . .
C39 C 0.28873(17) 0.64175(12) 0.21664(6) 0.0162(3) Uani 1 1 d . . . . .
C34 C 0.16969(18) 0.33591(13) 0.26198(6) 0.0208(3) Uani 1 1 d . . . . .
H34A H 0.073452 0.346134 0.255345 0.031 Uiso 1 1 calc GR . . . .
H34B H 0.209345 0.395975 0.274682 0.031 Uiso 1 1 calc GR . . . .
H34C H 0.180228 0.284133 0.286258 0.031 Uiso 1 1 calc GR . . . .
C41 C 0.20007(19) 0.72575(12) 0.20348(7) 0.0230(4) Uani 1 1 d . . . . .
C45 C 0.60627(19) 0.31625(13) -0.03385(6) 0.0217(3) Uani 1 1 d . . . . .
H45 H 0.636456 0.293104 -0.064729 0.026 Uiso 1 1 calc R . . . .
C21 C -0.17147(19) 0.49624(14) 0.15207(7) 0.0250(4) Uani 1 1 d . . . . .
H21 H -0.246124 0.520956 0.170010 0.030 Uiso 1 1 calc R . . . .
C9 C 0.13350(17) 0.37347(12) -0.06966(6) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.059285 0.341606 -0.054580 0.022 Uiso 1 1 calc R . . . .
F7A F 0.2568(17) 0.787(2) 0.178(3) 0.067(8) Uani 0.37(7) 1 d . . P A 2
F6A F 0.168(4) 0.773(3) 0.2491(13) 0.059(6) Uani 0.37(6) 1 d . . P A 2


_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 C19 1.7721(16) . ?
S1 C2 1.7771(16) . ?
S2 C25 1.7742(16) . ?
S2 C42 1.7725(16) . ?
F8 C41 1.336(2) . ?
F5 C36 1.3510(18) . ?
F1 C13 1.354(2) . ?
F3 C18 1.339(2) . ?
F2 C18 1.346(2) . ?
F4 C18 1.340(2) . ?
N1 C2 1.306(2) . ?
N1 C10 1.377(2) . ?
C25 N2 1.307(2) . ?
C25 C26 1.436(2) . ?
N2 C33 1.373(2) . ?
C19 C20 1.394(2) . ?
C19 C24 1.396(2) . ?
C12 C3 1.493(2) . ?
C12 C17 1.400(2) . ?
C12 C13 1.385(2) . ?
C40 C35 1.393(2) . ?
C40 C39 1.392(2) . ?
C4 C5 1.433(2) . ?
C4 C3 1.378(2) . ?
C4 C11 1.505(2) . ?
C2 C3 1.437(2) . ?
C29 C28 1.420(2) . ?
C29 C30 1.377(2) . ?
C42 C47 1.394(2) . ?
C42 C43 1.399(2) . ?
C5 C10 1.419(2) . ?
C5 C6 1.420(2) . ?
C10 C9 1.414(2) . ?
C35 C26 1.492(2) . ?
C35 C36 1.389(2) . ?
C47 C46 1.392(2) . ?
C22 C23 1.388(3) . ?
C22 C21 1.388(3) . ?
C6 C7 1.372(2) . ?
C28 C27 1.436(2) . ?
C28 C33 1.417(2) . ?
C7 C8 1.411(3) . ?
C37 C38 1.384(2) . ?
C37 C36 1.378(2) . ?
C31 C30 1.407(3) . ?
C31 C32 1.371(2) . ?
C15 C14 1.386(3) . ?
C15 C16 1.389(2) . ?
C26 C27 1.373(2) . ?
F7 C41 1.386(6) . ?
F6 C41 1.293(10) . ?
C8 C9 1.372(2) . ?
C38 C39 1.391(2) . ?
C17 C16 1.389(2) . ?
C18 C16 1.496(2) . ?
C46 C45 1.390(3) . ?
C27 C34 1.504(2) . ?
C20 C21 1.391(3) . ?
C24 C23 1.390(2) . ?
C14 C13 1.383(2) . ?
C43 C44 1.392(2) . ?
C33 C32 1.418(2) . ?
C44 C45 1.389(3) . ?
C39 C41 1.497(2) . ?
C41 F7A 1.24(2) . ?
C41 F6A 1.44(2) . ?

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
C19 S1 C2 107.23(8) . . ?
C42 S2 C25 105.35(7) . . ?
C2 N1 C10 117.25(14) . . ?
N2 C25 S2 120.96(12) . . ?
N2 C25 C26 124.45(14) . . ?
C26 C25 S2 114.59(11) . . ?
C25 N2 C33 117.24(14) . . ?
C20 C19 S1 115.36(13) . . ?
C20 C19 C24 120.11(15) . . ?
C24 C19 S1 123.75(13) . . ?
C17 C12 C3 121.77(14) . . ?
C13 C12 C3 121.67(15) . . ?
C13 C12 C17 116.56(15) . . ?
C39 C40 C35 120.26(15) . . ?
C5 C4 C11 119.86(14) . . ?
C3 C4 C5 118.27(15) . . ?
C3 C4 C11 121.86(15) . . ?
N1 C2 S1 120.49(12) . . ?
N1 C2 C3 125.18(14) . . ?
C3 C2 S1 114.30(12) . . ?
C30 C29 C28 120.52(16) . . ?
C47 C42 S2 122.11(13) . . ?
C47 C42 C43 120.51(15) . . ?
C43 C42 S2 117.11(13) . . ?
C10 C5 C4 118.54(14) . . ?
C10 C5 C6 118.58(15) . . ?
C6 C5 C4 122.87(15) . . ?
N1 C10 C5 122.50(14) . . ?
N1 C10 C9 118.02(14) . . ?
C9 C10 C5 119.48(15) . . ?
C40 C35 C26 122.43(14) . . ?
C36 C35 C40 117.23(14) . . ?
C36 C35 C26 120.34(14) . . ?
C4 C3 C12 121.86(15) . . ?
C4 C3 C2 118.22(14) . . ?
C2 C3 C12 119.91(14) . . ?
C46 C47 C42 119.56(15) . . ?
C21 C22 C23 119.79(17) . . ?
C7 C6 C5 120.86(16) . . ?
C29 C28 C27 123.08(15) . . ?
C33 C28 C29 118.65(15) . . ?
C33 C28 C27 118.23(14) . . ?
C6 C7 C8 120.16(16) . . ?
C36 C37 C38 118.60(15) . . ?
C32 C31 C30 120.20(16) . . ?
C14 C15 C16 119.56(15) . . ?
C25 C26 C35 118.90(13) . . ?
C27 C26 C25 119.11(14) . . ?
C27 C26 C35 121.99(14) . . ?
C9 C8 C7 120.38(16) . . ?
C37 C38 C39 119.54(15) . . ?
F5 C36 C35 118.29(14) . . ?
F5 C36 C37 118.25(15) . . ?
C37 C36 C35 123.45(15) . . ?
C16 C17 C12 120.64(15) . . ?
F3 C18 F2 105.76(14) . . ?
F3 C18 F4 106.42(15) . . ?
F3 C18 C16 112.45(15) . . ?
F2 C18 C16 112.47(14) . . ?
F4 C18 F2 105.98(15) . . ?
F4 C18 C16 113.19(14) . . ?
C45 C46 C47 120.04(16) . . ?
C28 C27 C34 120.56(14) . . ?
C26 C27 C28 117.83(14) . . ?
C26 C27 C34 121.61(14) . . ?
C29 C30 C31 120.54(16) . . ?
C21 C20 C19 119.88(16) . . ?
C23 C24 C19 119.32(16) . . ?
C13 C14 C15 118.34(16) . . ?
C44 C43 C42 119.35(16) . . ?
N2 C33 C28 122.95(14) . . ?
N2 C33 C32 117.56(14) . . ?
C28 C33 C32 119.48(15) . . ?
C45 C44 C43 120.18(16) . . ?
C22 C23 C24 120.73(16) . . ?
C31 C32 C33 120.57(16) . . ?
C15 C16 C18 118.70(15) . . ?
C17 C16 C15 120.90(15) . . ?
C17 C16 C18 120.38(15) . . ?
F1 C13 C12 118.37(15) . . ?
F1 C13 C14 117.62(15) . . ?
C14 C13 C12 124.00(16) . . ?
C40 C39 C41 119.82(15) . . ?
C38 C39 C40 120.87(15) . . ?
C38 C39 C41 119.26(15) . . ?
F8 C41 F7 101.3(4) . . ?
F8 C41 C39 113.27(14) . . ?
F8 C41 F6A 100.9(15) . . ?
F7 C41 C39 111.9(3) . . ?
F6 C41 F8 108.7(4) . . ?
F6 C41 F7 104.4(6) . . ?
F6 C41 C39 115.9(6) . . ?
F7A C41 F8 115(2) . . ?
F7A C41 C39 113.7(8) . . ?
F7A C41 F6A 106(4) . . ?
F6A C41 C39 105.7(11) . . ?
C44 C45 C46 120.35(16) . . ?
C22 C21 C20 120.14(17) . . ?
C8 C9 C10 120.52(16) . . ?

_olex2_date_sample_completion    2020-02-16
_olex2_date_sample_data_collection 2020-02-11
_olex2_date_sample_submission    2020-02-11
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.03(4)
2 -0.03(4)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Heat-sensitive
