# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_exp_12678
_database_code_depnum_ccdc_archive 'CCDC 2282710'
loop_
_audit_author_name
_audit_author_address
'Si-Hong Chen'
;South China Normal University 
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-03-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 F2 N2 S'
_chemical_formula_sum            'C24 H14 F2 N2 S'
_chemical_formula_weight         400.43
_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'
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                   6.7170(11)
_cell_length_b                   18.272(3)
_cell_length_c                   8.3004(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.832(18)
_cell_angle_gamma                90
_cell_volume                     964.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    865
_cell_measurement_temperature    297
_cell_measurement_theta_max      24.0050
_cell_measurement_theta_min      4.0700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3746
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.588
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  72.00   1.00    7.50    --   15.65 178.00 -30.00   29
  2  ω    -14.00  69.00   1.00    7.50    --   15.65  19.00 150.00   83
  3  ω    -54.00  44.00   1.00    7.50    --   15.65 -19.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0452576000
_diffrn_orient_matrix_UB_12      0.0051704000
_diffrn_orient_matrix_UB_13      -0.0890528000
_diffrn_orient_matrix_UB_21      -0.0794921000
_diffrn_orient_matrix_UB_22      0.0223561000
_diffrn_orient_matrix_UB_23      0.0136510000
_diffrn_orient_matrix_UB_31      0.0639342000
_diffrn_orient_matrix_UB_32      0.0313486000
_diffrn_orient_matrix_UB_33      0.0049592000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1057
_reflns_number_total             1684
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1684
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.1461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1357
_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. Rigid bond restraints
 S1, F1, F2, N1, N2, C5, C7, C9, C11, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: S1(0.5) F1(0.5) F2(0.5) N1(0.5) N2(0.5) C2(0.5) C7(0.5) C13(0.5)
 C14(0.5) C16(0.5) C17(0.5) C9(0.5) C5(0.5) C11(0.5) C15(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C10(H10), C12(H12)
5.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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 1.3052(3) 0.37955(10) 0.9372(2) 0.0812(5) Uani 0.5 1 d . U P A -1
F1 F 0.8935(10) 0.6261(6) 1.1719(15) 0.080(2) Uani 0.5 1 d . U P A -1
F2 F 0.5830(8) 0.5688(6) 0.9301(16) 0.0775(16) Uani 0.5 1 d . U P A -1
N1 N 1.0574(15) 0.3908(9) 0.842(2) 0.0694(19) Uani 0.5 1 d . U P A -1
N2 N 1.3523(14) 0.4462(8) 1.072(2) 0.0659(17) Uani 0.5 1 d . U P A -1
C1 C -0.0001(4) 0.32207(15) 0.2356(3) 0.0608(8) Uani 1 1 d . . . . .
C2 C 0.4821(14) 0.4184(10) 0.624(2) 0.060(3) Uani 0.5 1 d . . P A -1
C3 C -0.1840(4) 0.28753(18) 0.1029(4) 0.0932(11) Uani 1 1 d . . . . .
H3A H -0.171753 0.295545 -0.007821 0.140 Uiso 1 1 calc R U . . .
H3B H -0.312270 0.309089 0.107785 0.140 Uiso 1 1 calc R U . . .
H3C H -0.185472 0.235908 0.123967 0.140 Uiso 1 1 calc R U . . .
C4 C 0.3420(5) 0.38311(17) 0.4865(3) 0.0665(8) Uani 1 1 d . . . . .
C6 C 0.3691(4) 0.32689(16) 0.3833(4) 0.0704(9) Uani 1 1 d . . . . .
H6 H 0.503468 0.309059 0.397816 0.085 Uiso 1 1 calc R U . . .
C7 C 1.4469(17) 0.5921(10) 1.3883(19) 0.056(3) Uani 0.5 1 d . U P A -1
C8 C 0.2002(4) 0.29739(15) 0.2603(3) 0.0671(8) Uani 1 1 d . . . . .
H8 H 0.221715 0.259842 0.192085 0.081 Uiso 1 1 calc R U . . .
C10 C -0.0262(4) 0.37827(17) 0.3360(4) 0.0716(8) Uani 1 1 d . . . . .
H10 H -0.160690 0.396497 0.319402 0.086 Uiso 1 1 calc R U . . .
C12 C 0.1407(5) 0.40836(16) 0.4605(4) 0.0738(9) Uani 1 1 d . . . . .
H12 H 0.118015 0.446047 0.527835 0.089 Uiso 1 1 calc R U . . .
C13 C 1.3076(12) 0.5702(8) 1.2791(17) 0.064(2) Uani 0.5 1 d . U P A -1
C14 C 1.1396(13) 0.5403(6) 1.1449(14) 0.0537(17) Uani 0.5 1 d . U P A -1
C16 C 0.9400(13) 0.5672(10) 1.091(3) 0.057(2) Uani 0.5 1 d . U P A -1
C17 C 0.7717(16) 0.5359(8) 0.9654(19) 0.061(2) Uani 0.5 1 d . U P A -1
C9 C 0.7931(11) 0.4773(7) 0.8726(15) 0.0537(15) Uani 0.5 1 d . U P A -1
C5 C 0.9982(15) 0.4482(9) 0.912(2) 0.0524(16) Uani 0.5 1 d . U P A -1
C11 C 1.1728(12) 0.4796(7) 1.0515(17) 0.0495(14) Uani 0.5 1 d . U P A -1
C15 C 0.6232(13) 0.4459(9) 0.7371(18) 0.066(2) Uani 0.5 1 d . U P A -1


_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 N1 1.609(9) . ?
S1 N2 1.615(8) . ?
F1 C16 1.355(9) . ?
F2 C17 1.347(8) . ?
N1 C5 1.323(9) . ?
N2 C11 1.313(8) . ?
C1 C3 1.503(3) . ?
C1 C8 1.370(4) . ?
C1 C10 1.369(4) . ?
C2 C4 1.381(15) . ?
C2 C15 1.209(15) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C6 1.387(4) . ?
C4 C12 1.378(4) . ?
C6 H6 0.9300 . ?
C6 C8 1.369(3) . ?
C7 C13 1.145(15) . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C10 C12 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(9) . ?
C14 C16 1.361(9) . ?
C14 C11 1.411(10) . ?
C16 C17 1.391(10) . ?
C17 C9 1.353(10) . ?
C9 C5 1.413(9) . ?
C9 C15 1.438(9) . ?
C5 C11 1.472(10) . ?

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
N1 S1 N2 100.7(4) . . ?
C5 N1 S1 107.1(8) . . ?
C11 N2 S1 107.1(6) . . ?
C8 C1 C3 120.4(3) . . ?
C10 C1 C3 121.6(3) . . ?
C10 C1 C8 117.9(2) . . ?
C15 C2 C4 172.2(11) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C6 131.7(6) . . ?
C12 C4 C2 110.2(6) . . ?
C12 C4 C6 118.0(2) . . ?
C4 C6 H6 119.7 . . ?
C8 C6 C4 120.7(3) . . ?
C8 C6 H6 119.7 . . ?
C1 C8 H8 119.3 . . ?
C6 C8 C1 121.3(3) . . ?
C6 C8 H8 119.3 . . ?
C1 C10 H10 119.2 . . ?
C1 C10 C12 121.7(3) . . ?
C12 C10 H10 119.2 . . ?
C4 C12 H12 119.8 . . ?
C10 C12 C4 120.4(3) . . ?
C10 C12 H12 119.8 . . ?
C7 C13 C14 177.7(14) . . ?
C16 C14 C13 124.7(6) . . ?
C16 C14 C11 114.7(8) . . ?
C11 C14 C13 120.6(7) . . ?
F1 C16 C14 119.0(7) . . ?
F1 C16 C17 115.9(5) . . ?
C14 C16 C17 125.0(8) . . ?
F2 C17 C16 117.3(6) . . ?
F2 C17 C9 119.7(7) . . ?
C9 C17 C16 122.9(7) . . ?
C17 C9 C5 116.1(8) . . ?
C17 C9 C15 123.9(6) . . ?
C5 C9 C15 120.0(7) . . ?
N1 C5 C9 127.3(8) . . ?
N1 C5 C11 112.3(7) . . ?
C9 C5 C11 120.3(6) . . ?
N2 C11 C14 126.5(8) . . ?
N2 C11 C5 112.7(7) . . ?
C14 C11 C5 120.8(5) . . ?
C2 C15 C9 178.9(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C5 C9 -178(2) . . . . ?
S1 N1 C5 C11 -1(3) . . . . ?
S1 N2 C11 C14 178.8(15) . . . . ?
S1 N2 C11 C5 -3(2) . . . . ?
F1 C16 C17 F2 3(3) . . . . ?
F1 C16 C17 C9 179(2) . . . . ?
F2 C17 C9 C5 177(2) . . . . ?
F2 C17 C9 C15 -1(3) . . . . ?
N1 S1 N2 C11 1.7(18) . . . . ?
N1 C5 C11 N2 3(3) . . . . ?
N1 C5 C11 C14 -179(2) . . . . ?
N2 S1 N1 C5 0(2) . . . . ?
C1 C10 C12 C4 0.9(4) . . . . ?
C2 C4 C6 C8 175.5(10) . . . . ?
C2 C4 C12 C10 -176.6(8) . . . . ?
C3 C1 C8 C6 -178.4(2) . . . . ?
C3 C1 C10 C12 178.0(3) . . . . ?
C4 C6 C8 C1 -0.2(4) . . . . ?
C6 C4 C12 C10 0.1(4) . . . . ?
C8 C1 C10 C12 -1.4(4) . . . . ?
C10 C1 C8 C6 1.1(4) . . . . ?
C12 C4 C6 C8 -0.4(4) . . . . ?
C13 C14 C16 F1 -1(4) . . . . ?
C13 C14 C16 C17 -177(2) . . . . ?
C13 C14 C11 N2 -2(3) . . . . ?
C13 C14 C11 C5 179.8(19) . . . . ?
C14 C16 C17 F2 179(2) . . . . ?
C14 C16 C17 C9 -5(4) . . . . ?
C16 C14 C11 N2 176(2) . . . . ?
C16 C14 C11 C5 -2(2) . . . . ?
C16 C17 C9 C5 1(3) . . . . ?
C16 C17 C9 C15 -177(2) . . . . ?
C17 C9 C5 N1 179(2) . . . . ?
C17 C9 C5 C11 2(3) . . . . ?
C9 C5 C11 N2 180(2) . . . . ?
C9 C5 C11 C14 -2(3) . . . . ?
C11 C14 C16 F1 -179.2(19) . . . . ?
C11 C14 C16 C17 5(3) . . . . ?
C15 C9 C5 N1 -3(4) . . . . ?
C15 C9 C5 C11 -179.5(18) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_exp_12592
_database_code_depnum_ccdc_archive 'CCDC 2282714'
loop_
_audit_author_name
_audit_author_address
'Si-Hong Chen'
;South China Normal University 
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-02-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 F2 N2 O2 S'
_chemical_formula_sum            'C24 H14 F2 N2 O2 S'
_chemical_formula_weight         432.43
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.920(3)
_cell_length_b                   12.160(2)
_cell_length_c                   9.0331(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.902(17)
_cell_angle_gamma                90
_cell_volume                     2025.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    710
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.2190
_cell_measurement_theta_min      4.3630
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4643
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.714
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00  63.00   1.00   12.50    --   15.65  57.00 -60.00   49
  2  ω    -37.00   0.00   1.00   12.50    --  -16.43 -57.00 -90.00   37
  3  ω    -11.00  23.00   1.00   12.50    --  -16.43 -99.00  30.00   34
  4  ω    -52.00  32.00   1.00   12.50    --   15.65 -57.00 120.00   84
  5  ω     34.00  59.00   1.00   12.50    --   15.34  38.00 120.00   25
  6  ω    -21.00   5.00   1.00   12.50    --   15.34 -57.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053881000
_diffrn_orient_matrix_UB_12      0.0575539000
_diffrn_orient_matrix_UB_13      -0.0095673000
_diffrn_orient_matrix_UB_21      -0.0379677000
_diffrn_orient_matrix_UB_22      -0.0084216000
_diffrn_orient_matrix_UB_23      -0.0225153000
_diffrn_orient_matrix_UB_31      -0.0027570000
_diffrn_orient_matrix_UB_32      0.0046591000
_diffrn_orient_matrix_UB_33      0.0767672000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1181
_reflns_number_total             1789
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.022
_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)+(0.0493P)²+0.9468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1331
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 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 0.500000 0.35416(10) 0.750000 0.0501(4) Uani 1 2 d S T P . .
F1 F 0.44613(12) 0.83254(16) 0.6310(2) 0.0816(7) Uani 1 1 d . . . . .
O1 O 0.10121(11) 0.6623(2) -0.1274(2) 0.0641(7) Uani 1 1 d . . . . .
N1 N 0.44877(12) 0.4387(2) 0.6356(2) 0.0434(7) Uani 1 1 d . . . . .
C1 C 0.15815(15) 0.6516(3) -0.0054(3) 0.0451(8) Uani 1 1 d . . . . .
C2 C 0.20784(16) 0.5664(3) 0.0149(3) 0.0517(9) Uani 1 1 d . . . . .
H2 H 0.203854 0.510972 -0.057410 0.062 Uiso 1 1 calc R U . . .
C3 C 0.26330(17) 0.5644(3) 0.1430(3) 0.0519(9) Uani 1 1 d . . . . .
H3 H 0.296465 0.506809 0.156368 0.062 Uiso 1 1 calc R U . . .
C4 C 0.27086(15) 0.6455(3) 0.2518(3) 0.0415(8) Uani 1 1 d . . . . .
C5 C 0.22046(16) 0.7306(3) 0.2301(3) 0.0533(9) Uani 1 1 d . . . . .
H5 H 0.224328 0.785994 0.302382 0.064 Uiso 1 1 calc R U . . .
C6 C 0.16486(17) 0.7333(3) 0.1023(3) 0.0552(9) Uani 1 1 d . . . . .
H6 H 0.131626 0.790825 0.088639 0.066 Uiso 1 1 calc R U . . .
C7 C 0.32998(17) 0.6440(3) 0.3826(3) 0.0466(8) Uani 1 1 d . . . . .
C8 C 0.37980(17) 0.6422(3) 0.4899(3) 0.0476(8) Uani 1 1 d . . . . .
C9 C 0.43983(15) 0.6401(3) 0.6175(3) 0.0423(8) Uani 1 1 d . . . . .
C10 C 0.47088(18) 0.7336(3) 0.6863(3) 0.0523(9) Uani 1 1 d . . . . .
C11 C 0.47043(14) 0.5394(3) 0.6845(3) 0.0374(7) Uani 1 1 d . . . . .
C12 C 0.09818(19) 0.5910(3) -0.2533(4) 0.0707(11) Uani 1 1 d . . . . .
H12A H 0.092600 0.516439 -0.222805 0.106 Uiso 1 1 calc R U . . .
H12B H 0.142207 0.597522 -0.288754 0.106 Uiso 1 1 calc R U . . .
H12C H 0.057691 0.610796 -0.333493 0.106 Uiso 1 1 calc R U . . .


_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 N1 1.618(2) 2_656 ?
S1 N1 1.618(2) . ?
F1 C10 1.346(3) . ?
O1 C1 1.364(3) . ?
O1 C12 1.422(4) . ?
N1 C11 1.335(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.376(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 C5 1.391(4) . ?
C4 C7 1.435(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.191(4) . ?
C8 C9 1.426(4) . ?
C9 C10 1.365(4) . ?
C9 C11 1.430(4) . ?
C10 C10 1.404(6) 2_656 ?
C11 C11 1.435(5) 2_656 ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
N1 S1 N1 101.12(19) 2_656 . ?
C1 O1 C12 118.1(3) . . ?
C11 N1 S1 105.98(19) . . ?
O1 C1 C2 124.7(3) . . ?
O1 C1 C6 115.7(3) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 C7 121.1(3) . . ?
C5 C4 C7 120.6(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C4 179.0(3) . . ?
C7 C8 C9 179.6(3) . . ?
C8 C9 C11 122.1(3) . . ?
C10 C9 C8 122.5(3) . . ?
C10 C9 C11 115.4(3) . . ?
F1 C10 C9 119.8(3) . . ?
F1 C10 C10 116.66(17) . 2_656 ?
C9 C10 C10 123.55(17) . 2_656 ?
N1 C11 C9 125.5(3) . . ?
N1 C11 C11 113.46(15) . 2_656 ?
C9 C11 C11 121.08(16) . 2_656 ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C11 C9 -179.6(2) . . . . ?
S1 N1 C11 C11 0.4(4) . . . 2_656 ?
O1 C1 C2 C3 180.0(3) . . . . ?
O1 C1 C6 C5 180.0(3) . . . . ?
N1 S1 N1 C11 -0.17(13) 2_656 . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C2 C3 C4 C7 -178.3(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C7 C4 C5 C6 178.2(3) . . . . ?
C8 C9 C10 F1 -1.9(5) . . . . ?
C8 C9 C10 C10 178.8(4) . . . 2_656 ?
C8 C9 C11 N1 1.8(4) . . . . ?
C8 C9 C11 C11 -178.3(3) . . . 2_656 ?
C10 C9 C11 N1 -179.7(3) . . . . ?
C10 C9 C11 C11 0.2(5) . . . 2_656 ?
C11 C9 C10 F1 179.6(3) . . . . ?
C11 C9 C10 C10 0.4(5) . . . 2_656 ?
C12 O1 C1 C2 -9.8(4) . . . . ?
C12 O1 C1 C6 169.9(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.163
_oxdiff_exptl_absorpt_empirical_full_min 0.796
####################################################################### 
# 
# 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_exp_12591
_database_code_depnum_ccdc_archive 'CCDC 2282718'
loop_
_audit_author_name
_audit_author_address
'Si-Hong Chen'
;South China Normal University 
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-02-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10.161 Br0.839 F2 N3 S'
_chemical_formula_sum            'C16 H10.16 Br0.84 F2 N3 S'
_chemical_formula_weight         381.62
_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'
Br Br -0.2901 2.4595 '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'
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      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                   7.0240(8)
_cell_length_b                   10.3191(9)
_cell_length_c                   11.3416(14)
_cell_angle_alpha                90.378(9)
_cell_angle_beta                 105.741(10)
_cell_angle_gamma                98.561(8)
_cell_volume                     781.46(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    297
_cell_measurement_theta_max      24.6980
_cell_measurement_theta_min      3.9100
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.648
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             381
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5693
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  -4.00   1.00    7.50    --   15.65 -57.00 -90.00   27
  2  ω    -20.00  14.00   1.00    7.50    --  -16.43 -99.00-120.00   34
  3  ω    -52.00  23.00   1.00    7.50    --   15.65 -57.00-150.00   75
  4  ω    -50.00  42.00   1.00    7.50    --   15.65 -77.00 -30.00   92
  5  ω     33.00  88.00   1.00    7.50    --   15.65-178.00 120.00   55
  6  ω    -24.00  23.00   1.00    7.50    --  -16.43 -99.00 120.00   47
  7  ω     23.00  83.00   1.00    7.50    --   15.65  77.00  90.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0734538000
_diffrn_orient_matrix_UB_12      -0.0564885000
_diffrn_orient_matrix_UB_13      -0.0202434000
_diffrn_orient_matrix_UB_21      -0.0556975000
_diffrn_orient_matrix_UB_22      0.0362155000
_diffrn_orient_matrix_UB_23      -0.0462994000
_diffrn_orient_matrix_UB_31      0.0527864000
_diffrn_orient_matrix_UB_32      -0.0184698000
_diffrn_orient_matrix_UB_33      -0.0409736000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1958
_reflns_number_total             2757
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.081
_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)+(0.0237P)²+0.5397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1000
_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. Others
 Sof(H1)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C10(H10), C12(H12), C13(H13)
3.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c)
;
_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
Br1 Br 0.30036(9) 0.18835(6) 1.04310(5) 0.0673(3) Uani 0.839(3) 1 d . . P A 1
S1 S 0.09013(17) 0.58305(12) 0.86770(11) 0.0624(4) Uani 1 1 d . . . . .
F1 F 0.6168(4) 0.1738(3) 0.9053(2) 0.0753(8) Uani 1 1 d . . . . .
F2 F 0.7312(4) 0.3309(3) 0.7494(2) 0.0738(8) Uani 1 1 d . . . . .
N1 N 0.9176(6) 0.9690(4) 0.2852(4) 0.0679(12) Uani 1 1 d . . . . .
N2 N 0.2439(5) 0.5972(3) 0.7836(3) 0.0545(10) Uani 1 1 d . . . . .
N3 N 0.1429(5) 0.4517(3) 0.9382(3) 0.0540(9) Uani 1 1 d . . . . .
C1 C 0.3792(6) 0.3008(4) 0.9304(4) 0.0484(11) Uani 1 1 d . . . . .
H1 H 0.342462 0.245066 0.987336 0.058 Uiso 0.161(3) 1 calc R U P A 2
C2 C 0.5221(6) 0.2787(4) 0.8781(4) 0.0530(11) Uani 1 1 d . . . . .
C3 C 0.5025(6) 0.4731(4) 0.7565(4) 0.0481(11) Uani 1 1 d . . . . .
C4 C 0.3460(6) 0.4972(4) 0.8081(3) 0.0432(10) Uani 1 1 d . . . . .
C5 C 0.2874(6) 0.4121(4) 0.8954(3) 0.0448(10) Uani 1 1 d . . . . .
C6 C 0.5722(6) 0.5600(4) 0.6749(4) 0.0565(12) Uani 1 1 d . . . . .
C7 C 0.6326(6) 0.6304(4) 0.6067(4) 0.0566(12) Uani 1 1 d . . . . .
C8 C 0.7072(6) 0.7171(4) 0.5264(4) 0.0491(11) Uani 1 1 d . . . . .
C9 C 0.8734(6) 0.6984(4) 0.4874(4) 0.0543(12) Uani 1 1 d . . . . .
H9 H 0.938665 0.627852 0.515321 0.065 Uiso 1 1 calc R U . . .
C10 C 0.9433(6) 0.7807(4) 0.4093(4) 0.0552(12) Uani 1 1 d . . . . .
H10 H 1.055480 0.765428 0.385966 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8494(6) 0.8873(4) 0.3640(4) 0.0490(11) Uani 1 1 d . . . . .
C12 C 0.6822(7) 0.9054(4) 0.4032(4) 0.0588(12) Uani 1 1 d . . . . .
H12 H 0.615667 0.975468 0.375251 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6148(7) 0.8231(4) 0.4812(4) 0.0572(12) Uani 1 1 d . . . . .
H13 H 0.503066 0.838473 0.505019 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8217(8) 1.0812(5) 0.2395(5) 0.0856(17) Uani 1 1 d . . . . .
H14A H 0.681091 1.052657 0.203639 0.128 Uiso 1 1 calc R U . . .
H14B H 0.880214 1.121054 0.178707 0.128 Uiso 1 1 calc R U . . .
H14C H 0.840465 1.143914 0.306171 0.128 Uiso 1 1 calc R U . . .
C15 C 1.0965(7) 0.9528(5) 0.2494(5) 0.0850(17) Uani 1 1 d . . . . .
H15A H 1.123387 1.020904 0.196194 0.127 Uiso 1 1 calc R U . . .
H15B H 1.076349 0.868823 0.207089 0.127 Uiso 1 1 calc R U . . .
H15C H 1.208133 0.957868 0.321218 0.127 Uiso 1 1 calc R U . . .
C16 C 0.5838(6) 0.3631(4) 0.7939(4) 0.0528(11) Uani 1 1 d . . . . .


_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
Br1 C1 1.870(4) . ?
S1 N2 1.616(4) . ?
S1 N3 1.618(3) . ?
F1 C2 1.349(4) . ?
F2 C16 1.349(4) . ?
N1 C11 1.364(5) . ?
N1 C14 1.454(5) . ?
N1 C15 1.453(6) . ?
N2 C4 1.331(5) . ?
N3 C5 1.350(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.343(6) . ?
C1 C5 1.407(5) . ?
C2 C16 1.407(6) . ?
C3 C4 1.429(5) . ?
C3 C6 1.423(5) . ?
C3 C16 1.365(6) . ?
C4 C5 1.430(5) . ?
C6 C7 1.183(5) . ?
C7 C8 1.426(6) . ?
C8 C9 1.394(6) . ?
C8 C13 1.385(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(5) . ?
C11 C12 1.400(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.358(6) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
N2 S1 N3 100.99(18) . . ?
C11 N1 C14 121.3(4) . . ?
C11 N1 C15 121.6(4) . . ?
C15 N1 C14 117.0(4) . . ?
C4 N2 S1 106.4(3) . . ?
C5 N3 S1 105.8(3) . . ?
C2 C1 Br1 122.1(3) . . ?
C2 C1 H1 121.5 . . ?
C2 C1 C5 117.0(4) . . ?
C5 C1 Br1 120.9(3) . . ?
C5 C1 H1 121.5 . . ?
F1 C2 C16 116.2(4) . . ?
C1 C2 F1 121.1(4) . . ?
C1 C2 C16 122.7(4) . . ?
C6 C3 C4 122.2(4) . . ?
C16 C3 C4 115.1(4) . . ?
C16 C3 C6 122.6(4) . . ?
N2 C4 C3 125.5(4) . . ?
N2 C4 C5 113.7(4) . . ?
C3 C4 C5 120.8(4) . . ?
N3 C5 C1 126.0(4) . . ?
N3 C5 C4 113.1(4) . . ?
C1 C5 C4 120.9(4) . . ?
C7 C6 C3 178.6(5) . . ?
C6 C7 C8 178.9(5) . . ?
C9 C8 C7 122.0(4) . . ?
C13 C8 C7 121.4(4) . . ?
C13 C8 C9 116.6(4) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.0(4) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
N1 C11 C10 121.3(4) . . ?
N1 C11 C12 122.1(4) . . ?
C10 C11 C12 116.6(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 122.1(4) . . ?
C12 C13 H13 119.0 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F2 C16 C2 116.8(4) . . ?
F2 C16 C3 119.8(4) . . ?
C3 C16 C2 123.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 F1 -0.4(6) . . . . ?
Br1 C1 C2 C16 -179.5(3) . . . . ?
Br1 C1 C5 N3 1.7(6) . . . . ?
Br1 C1 C5 C4 -179.3(3) . . . . ?
S1 N2 C4 C3 -178.2(3) . . . . ?
S1 N2 C4 C5 0.9(4) . . . . ?
S1 N3 C5 C1 -179.6(3) . . . . ?
S1 N3 C5 C4 1.3(4) . . . . ?
F1 C2 C16 F2 -0.2(6) . . . . ?
F1 C2 C16 C3 179.7(4) . . . . ?
N1 C11 C12 C13 179.6(4) . . . . ?
N2 S1 N3 C5 -0.7(3) . . . . ?
N2 C4 C5 N3 -1.5(5) . . . . ?
N2 C4 C5 C1 179.3(4) . . . . ?
N3 S1 N2 C4 -0.1(3) . . . . ?
C1 C2 C16 F2 179.0(4) . . . . ?
C1 C2 C16 C3 -1.1(7) . . . . ?
C2 C1 C5 N3 -179.3(4) . . . . ?
C2 C1 C5 C4 -0.3(6) . . . . ?
C3 C4 C5 N3 177.7(3) . . . . ?
C3 C4 C5 C1 -1.4(6) . . . . ?
C4 C3 C16 F2 179.3(3) . . . . ?
C4 C3 C16 C2 -0.6(6) . . . . ?
C5 C1 C2 F1 -179.3(4) . . . . ?
C5 C1 C2 C16 1.5(6) . . . . ?
C6 C3 C4 N2 2.8(6) . . . . ?
C6 C3 C4 C5 -176.3(4) . . . . ?
C6 C3 C16 F2 -2.6(6) . . . . ?
C6 C3 C16 C2 177.5(4) . . . . ?
C7 C8 C9 C10 179.2(4) . . . . ?
C7 C8 C13 C12 -179.0(4) . . . . ?
C8 C9 C10 C11 -0.6(7) . . . . ?
C9 C8 C13 C12 -0.2(7) . . . . ?
C9 C10 C11 N1 -179.4(4) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.2(7) . . . . ?
C11 C12 C13 C8 0.1(7) . . . . ?
C13 C8 C9 C10 0.5(6) . . . . ?
C14 N1 C11 C10 -179.0(4) . . . . ?
C14 N1 C11 C12 1.2(7) . . . . ?
C15 N1 C11 C10 -3.0(7) . . . . ?
C15 N1 C11 C12 177.2(4) . . . . ?
C16 C3 C4 N2 -179.1(4) . . . . ?
C16 C3 C4 C5 1.8(6) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.728
####################################################################### 
# 
# 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_exp_13540
_database_code_depnum_ccdc_archive 'CCDC 2282717'
loop_
_audit_author_name
_audit_author_address
'Si-Hong Chen'
;South China Normal University 
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 F2 N4 S'
_chemical_formula_sum            'C26 H20 F2 N4 S'
_chemical_formula_weight         458.52
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7592(10)
_cell_length_b                   15.080(2)
_cell_length_c                   19.199(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.781(11)
_cell_angle_gamma                90
_cell_volume                     2241.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    297
_cell_measurement_theta_max      25.4620
_cell_measurement_theta_min      4.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12199
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.489
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  44.00   1.00    5.00    --  -16.59   0.00  30.00   26
  2  ω     34.00  61.00   1.00    5.00    --   15.65  57.00   0.00   27
  3  ω     -1.00  31.00   1.00    5.00    --   15.65  57.00   0.00   32
  4  ω    -18.00  19.00   1.00    5.00    --  -16.59 -99.00 120.00   37
  5  ω    -25.00   1.00   1.00    5.00    --  -16.59 -99.00  90.00   26
  6  ω    -71.00 -22.00   1.00    5.00    --  -16.59   0.00  30.00   49
  7  ω     -1.00  62.00   1.00    5.00    --   15.65  57.00-120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0487117000
_diffrn_orient_matrix_UB_12      0.0395872000
_diffrn_orient_matrix_UB_13      0.0028168000
_diffrn_orient_matrix_UB_21      0.0608385000
_diffrn_orient_matrix_UB_22      0.0233044000
_diffrn_orient_matrix_UB_23      -0.0190210000
_diffrn_orient_matrix_UB_31      -0.0479820000
_diffrn_orient_matrix_UB_32      -0.0105838000
_diffrn_orient_matrix_UB_33      -0.0315855000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2909
_reflns_number_total             5194
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5194
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.095
_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)+(0.0364P)²+1.1611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1552
_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. Shared sites
{F1, N6A}
{F2, N3A}
{N6, F1A}
{N3, F2A}
3. Uiso/Uaniso restraints and constraints
S1 \\sim S1A \\sim F1 \\sim F1A \\sim F2 \\sim F2A \\sim N3 \\sim N3A \\sim N6
\\sim N6A \\sim C13 \\sim C22 \\sim C26: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
Uanis(F1) = Uanis(N6A)
Uanis(F2) = Uanis(N3A)
Uanis(N6) = Uanis(F1A)
Uanis(N3) = Uanis(F2A)
4. Others
 Sof(S1A)=Sof(F1A)=Sof(F2A)=Sof(N3A)=Sof(N6A)=1-FVAR(1)
 Sof(S1)=Sof(F1)=Sof(F2)=Sof(N3)=Sof(N6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C14(H14), C16(H16), C18(H18), C20(H20), C24(H24)
5.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C23(H23A,H23B,H23C), 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
S1 S 0.42915(16) 0.58583(8) 0.78203(6) 0.0720(4) Uani 0.797(2) 1 d . U P A 1
S1A S 0.7159(6) 0.3738(3) 0.5103(3) 0.0762(16) Uani 0.203(2) 1 d . U P A 2
F1 F 0.7163(3) 0.48319(14) 0.51587(10) 0.0768(6) Uani 0.797(2) 1 d . U P A 1
F1A F 0.5013(3) 0.63085(18) 0.71354(13) 0.0710(7) Uani 0.203(2) 1 d . U P A 2
F2 F 0.6721(3) 0.33162(13) 0.57545(11) 0.0770(6) Uani 0.797(2) 1 d . U P A 1
F2A F 0.4575(3) 0.48338(18) 0.77132(13) 0.0744(8) Uani 0.203(2) 1 d . U P A 2
N2 N 0.7713(3) 1.07984(18) 0.47874(14) 0.0629(7) Uani 1 1 d . . . . .
N3 N 0.4575(3) 0.48338(18) 0.77132(13) 0.0744(8) Uani 0.797(2) 1 d . U P A 1
N3A N 0.6721(3) 0.33162(13) 0.57545(11) 0.0770(6) Uani 0.203(2) 1 d . U P A 2
N5 N 0.4466(4) -0.10505(18) 0.84012(14) 0.0665(8) Uani 1 1 d . . . . .
N6 N 0.5013(3) 0.63085(18) 0.71354(13) 0.0710(7) Uani 0.797(2) 1 d . U P A 1
N6A N 0.7163(3) 0.48319(14) 0.51587(10) 0.0768(6) Uani 0.203(2) 1 d . U P A 2
C1 C 0.5136(4) 0.1522(2) 0.76255(16) 0.0522(8) Uani 1 1 d . . . . .
C2 C 0.5465(4) 0.5603(2) 0.67542(15) 0.0505(7) Uani 1 1 d . . . . .
C3 C 0.3795(5) -0.1199(2) 0.90764(18) 0.0777(11) Uani 1 1 d . . . . .
H3A H 0.446144 -0.086528 0.942434 0.117 Uiso 1 1 calc R U . . .
H3B H 0.386836 -0.181908 0.918884 0.117 Uiso 1 1 calc R U . . .
H3C H 0.261095 -0.101253 0.906440 0.117 Uiso 1 1 calc R U . . .
C4 C 0.6538(4) 0.8435(2) 0.46768(15) 0.0530(8) Uani 1 1 d . . . . .
H4 H 0.606419 0.803901 0.434587 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4466(4) 0.1378(2) 0.82682(16) 0.0600(8) Uani 1 1 d . . . . .
H5 H 0.415612 0.186310 0.853152 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6982(4) 0.8137(2) 0.53494(15) 0.0493(7) Uani 1 1 d . . . . .
C7 C 0.6145(4) 0.5666(2) 0.60873(16) 0.0523(8) Uani 1 1 d . . . . .
C8 C 0.7480(3) 0.99285(19) 0.49663(15) 0.0473(7) Uani 1 1 d . . . . .
C9 C 0.5645(4) 0.3952(2) 0.67601(16) 0.0536(8) Uani 1 1 d . . . . .
C10 C 0.6782(4) 0.9302(2) 0.44903(15) 0.0514(7) Uani 1 1 d . . . . .
H10 H 0.647520 0.947780 0.403463 0.062 Uiso 1 1 calc R U . . .
C11 C 0.7199(5) 1.1125(2) 0.40971(19) 0.0798(11) Uani 1 1 d . . . . .
H11A H 0.792528 1.086887 0.376474 0.120 Uiso 1 1 calc R U . . .
H11B H 0.731140 1.175913 0.408966 0.120 Uiso 1 1 calc R U . . .
H11C H 0.601872 1.096500 0.397832 0.120 Uiso 1 1 calc R U . . .
C12 C 0.4680(3) -0.0213(2) 0.81502(15) 0.0485(7) Uani 1 1 d . . . . .
C13 C 0.5213(4) 0.4761(2) 0.70794(15) 0.0529(8) Uani 1 1 d . U . . .
C14 C 0.7959(4) 0.9620(2) 0.56383(15) 0.0557(8) Uani 1 1 d . . . . .
H14 H 0.846082 1.001033 0.596706 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5315(4) 0.2388(2) 0.73426(17) 0.0623(9) Uani 1 1 d . . . . .
C16 C 0.5372(4) -0.0067(2) 0.75052(15) 0.0546(8) Uani 1 1 d . . . . .
H16 H 0.568287 -0.055005 0.723986 0.065 Uiso 1 1 calc R U . . .
C17 C 0.6678(4) 0.7242(2) 0.55631(16) 0.0574(8) Uani 1 1 d . . . . .
C18 C 0.7704(4) 0.8752(2) 0.58236(16) 0.0580(8) Uani 1 1 d . . . . .
H18 H 0.802217 0.857157 0.627715 0.070 Uiso 1 1 calc R U . . .
C19 C 0.6437(4) 0.6508(2) 0.57781(17) 0.0606(9) Uani 1 1 d . . . . .
C20 C 0.5603(4) 0.0774(2) 0.72560(15) 0.0557(8) Uani 1 1 d . . . . .
H20 H 0.608341 0.084755 0.682865 0.067 Uiso 1 1 calc R U . . .
C21 C 0.5444(4) 0.3108(2) 0.70831(18) 0.0662(9) Uani 1 1 d . . . . .
C22 C 0.6266(4) 0.4038(2) 0.61180(17) 0.0539(8) Uani 1 1 d . U . . .
C23 C 0.8444(5) 1.1434(2) 0.5290(2) 0.0796(11) Uani 1 1 d . . . . .
H23A H 0.770606 1.148628 0.566979 0.119 Uiso 1 1 calc R U . . .
H23B H 0.854184 1.200113 0.506788 0.119 Uiso 1 1 calc R U . . .
H23C H 0.956709 1.123739 0.546388 0.119 Uiso 1 1 calc R U . . .
C24 C 0.4247(4) 0.0540(2) 0.85263(15) 0.0557(8) Uani 1 1 d . . . . .
H24 H 0.380146 0.047084 0.896094 0.067 Uiso 1 1 calc R U . . .
C25 C 0.4617(5) -0.1819(2) 0.7959(2) 0.0842(11) Uani 1 1 d . . . . .
H25A H 0.390856 -0.173922 0.753453 0.126 Uiso 1 1 calc R U . . .
H25B H 0.424234 -0.233726 0.819761 0.126 Uiso 1 1 calc R U . . .
H25C H 0.579919 -0.189208 0.785142 0.126 Uiso 1 1 calc R U . . .
C26 C 0.6509(4) 0.4862(2) 0.57901(15) 0.0540(8) Uani 1 1 d . U . . .


_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 N3 1.576(3) . ?
S1 N6 1.613(3) . ?
S1A N3A 1.463(5) . ?
S1A N6A 1.653(5) . ?
S1A C22 2.158(6) . ?
S1A C26 2.225(6) . ?
F1 C26 1.345(3) . ?
F1A C2 1.351(4) . ?
F2 C22 1.353(3) . ?
F2A C13 1.348(4) . ?
N2 C8 1.371(4) . ?
N2 C11 1.445(4) . ?
N2 C23 1.449(4) . ?
N3 C13 1.348(4) . ?
N3A C22 1.353(3) . ?
N5 C3 1.446(4) . ?
N5 C12 1.365(4) . ?
N5 C25 1.446(4) . ?
N6 C2 1.351(4) . ?
N6A C26 1.345(3) . ?
C1 C5 1.387(4) . ?
C1 C15 1.426(4) . ?
C1 C20 1.392(4) . ?
C2 C7 1.420(4) . ?
C2 C13 1.434(4) . ?
C4 C6 1.389(4) . ?
C4 C10 1.371(4) . ?
C5 C24 1.372(4) . ?
C6 C17 1.434(4) . ?
C6 C18 1.392(4) . ?
C7 C19 1.426(4) . ?
C7 C26 1.378(4) . ?
C8 C10 1.399(4) . ?
C8 C14 1.399(4) . ?
C9 C13 1.415(4) . ?
C9 C21 1.429(4) . ?
C9 C22 1.359(4) . ?
C12 C16 1.400(4) . ?
C12 C24 1.398(4) . ?
C14 C18 1.373(4) . ?
C15 C21 1.201(4) . ?
C16 C20 1.372(4) . ?
C17 C19 1.201(4) . ?
C22 C26 1.410(4) . ?

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
N3 S1 N6 104.32(15) . . ?
N3A S1A N6A 112.3(3) . . ?
N3A S1A C22 38.11(16) . . ?
N3A S1A C26 75.5(2) . . ?
N6A S1A C22 74.5(2) . . ?
N6A S1A C26 37.02(14) . . ?
C22 S1A C26 37.50(13) . . ?
C8 N2 C11 121.5(3) . . ?
C8 N2 C23 121.3(3) . . ?
C11 N2 C23 117.2(3) . . ?
C13 N3 S1 105.1(2) . . ?
C22 N3A S1A 100.0(3) . . ?
C3 N5 C25 116.7(3) . . ?
C12 N5 C3 121.3(3) . . ?
C12 N5 C25 121.2(3) . . ?
C2 N6 S1 103.1(2) . . ?
C26 N6A S1A 95.3(3) . . ?
C5 C1 C15 122.3(3) . . ?
C5 C1 C20 116.9(3) . . ?
C20 C1 C15 120.9(3) . . ?
F1A C2 C7 124.1(3) . . ?
F1A C2 C13 114.5(3) . . ?
N6 C2 C7 124.1(3) . . ?
N6 C2 C13 114.5(3) . . ?
C7 C2 C13 121.5(3) . . ?
C10 C4 C6 121.4(3) . . ?
C24 C5 C1 121.9(3) . . ?
C4 C6 C17 122.4(3) . . ?
C4 C6 C18 117.2(3) . . ?
C18 C6 C17 120.5(3) . . ?
C2 C7 C19 121.0(3) . . ?
C26 C7 C2 114.4(3) . . ?
C26 C7 C19 124.7(3) . . ?
N2 C8 C10 122.3(3) . . ?
N2 C8 C14 121.2(3) . . ?
C10 C8 C14 116.5(3) . . ?
C13 C9 C21 122.9(3) . . ?
C22 C9 C13 114.8(3) . . ?
C22 C9 C21 122.3(3) . . ?
C4 C10 C8 121.8(3) . . ?
N5 C12 C16 121.4(3) . . ?
N5 C12 C24 122.0(3) . . ?
C24 C12 C16 116.6(3) . . ?
F2A C13 C2 112.9(3) . . ?
F2A C13 C9 124.9(3) . . ?
N3 C13 C2 112.9(3) . . ?
N3 C13 C9 124.9(3) . . ?
C9 C13 C2 122.1(3) . . ?
C18 C14 C8 121.5(3) . . ?
C21 C15 C1 177.8(4) . . ?
C20 C16 C12 121.4(3) . . ?
C19 C17 C6 176.5(3) . . ?
C14 C18 C6 121.6(3) . . ?
C17 C19 C7 175.4(4) . . ?
C16 C20 C1 121.8(3) . . ?
C15 C21 C9 178.0(4) . . ?
F2 C22 C9 120.8(3) . . ?
F2 C22 C26 115.5(3) . . ?
N3A C22 S1A 41.86(18) . . ?
N3A C22 C9 120.8(3) . . ?
N3A C22 C26 115.5(3) . . ?
C9 C22 S1A 162.4(3) . . ?
C9 C22 C26 123.7(3) . . ?
C26 C22 S1A 73.8(2) . . ?
C5 C24 C12 121.5(3) . . ?
F1 C26 C7 120.1(3) . . ?
F1 C26 C22 116.3(3) . . ?
N6A C26 S1A 47.70(19) . . ?
N6A C26 C7 120.1(3) . . ?
N6A C26 C22 116.3(3) . . ?
C7 C26 S1A 167.5(3) . . ?
C7 C26 C22 123.6(3) . . ?
C22 C26 S1A 68.7(2) . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.840
