# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1250
_database_code_depnum_ccdc_archive 'CCDC 2116297'
loop_
_audit_author_name
_audit_author_address
shihongsong
;Tianjin University
China
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_audit_creation_date             2021-01-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 F2 N4 O2 S'
_chemical_formula_sum            'C15 H12 F2 N4 O2 S'
_chemical_formula_weight         350.35
_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'
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           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   5.4470(4)
_cell_length_b                   26.496(4)
_cell_length_c                   11.3845(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.428(7)
_cell_angle_gamma                90
_cell_volume                     1604.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3430
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      24.5630
_cell_measurement_theta_min      1.9970
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10241
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.986
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  40.00   0.50    6.00    --    5.00  14.00  60.00   94
  2  ω    -24.00  79.00   0.50    6.00    --   -9.60  55.00   0.00  206
  3  ω    -58.00 -32.00   0.50    6.00    --   -9.60  43.00  90.00   52
  4  ω    -25.00  77.00   0.50    6.00    --   -9.60  55.00-120.00  204
  5  ω    -99.00 -62.00   0.50    6.00    --   -9.60  43.00 150.00   74
  6  ω    -47.00  55.00   0.50    6.00    --   -9.60  43.00 150.00  204
  7  ω    -79.00 -50.00   0.50    6.00    --   -9.60  55.00-120.00   58
  8  ω     -7.00  19.00   0.50    6.00    --   -9.60  43.00  90.00   52
  9  ω    -26.00  78.00   0.50    6.00    --   -9.60  55.00 120.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0679207000
_diffrn_orient_matrix_UB_12      -0.0231596000
_diffrn_orient_matrix_UB_13      -0.0101111000
_diffrn_orient_matrix_UB_21      0.0059094000
_diffrn_orient_matrix_UB_22      -0.0468294000
_diffrn_orient_matrix_UB_23      -0.0036328000
_diffrn_orient_matrix_UB_31      0.0118748000
_diffrn_orient_matrix_UB_32      0.0117096000
_diffrn_orient_matrix_UB_33      0.0471622000
_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         0.777
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.784
_reflns_number_gt                2258
_reflns_number_total             2544
_reflns_odcompleteness_completeness 98.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 
;
 Flack x determined using 869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.072
_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)+(0.1803P)²+4.6897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2488
_refine_ls_wR_factor_ref         0.2626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C00K, C8, C3, C4, C2, C00J
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 F002, F007
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C00K \\sim C8 \\sim C3 \\sim C4 \\sim C2 \\sim C00J: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
Uanis(C00K) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C00J) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(F002) \\sim Ueq, Uanis(F007) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00I(H00I), C00H(H00H), C00A(H00A), C00E(H00E), C2(H2),
 C00K(H00K), C8(H8), C3(H3), C4(H4)
4.b Fitted hexagon refined as free rotating group:
 C00F(C00I,C00H,C00C,C00A,C00E), C2(C00J,C00K,C8,C3,C4)
4.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O1(H1)
;
_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
S001 S 0.8350(6) 0.34805(11) 0.7682(4) 0.0746(11) Uani 1 1 d . . . . .
F002 F 0.5252(12) 0.3623(3) 0.8984(5) 0.0639(19) Uani 1 1 d . U . . .
O003 O 0.7101(12) 0.4547(2) 0.8230(5) 0.0358(14) Uani 1 1 d . . . . .
H003 H 0.715185 0.484441 0.803958 0.054 Uiso 1 1 calc R U . . .
O1 O 0.2914(11) 0.4474(2) 0.7469(5) 0.0353(13) Uani 1 1 d . . . . .
H1 H 0.199702 0.448237 0.679617 0.053 Uiso 1 1 calc R U . . .
N N 0.5145(13) 0.4372(3) 0.4271(6) 0.0347(16) Uani 1 1 d . . . . .
N006 N 0.7951(14) 0.4455(3) 0.5856(6) 0.0380(17) Uani 1 1 d . . . . .
F007 F 0.3590(14) 0.3484(2) 0.6986(7) 0.074(2) Uani 1 1 d . U . . .
N008 N 0.3886(13) 0.4296(3) 0.5146(6) 0.0338(16) Uani 1 1 d . . . . .
N009 N 0.7561(15) 0.4471(3) 0.4654(7) 0.0402(17) Uani 1 1 d . . . . .
C00B C 0.5305(15) 0.4298(3) 0.7386(7) 0.0301(17) Uani 1 1 d . . . . .
C00D C 0.5727(15) 0.4356(3) 0.6121(7) 0.0315(17) Uani 1 1 d . . . . .
C00F C 0.1768(12) 0.4234(3) 0.0615(4) 0.062(3) Uani 1 1 d G . . . .
H00F H 0.102317 0.420330 -0.019746 0.075 Uiso 1 1 calc R U . . .
C00I C 0.0581(11) 0.4036(3) 0.1478(5) 0.068(3) Uani 1 1 d G . . . .
H00I H -0.095805 0.387304 0.124324 0.082 Uiso 1 1 calc R U . . .
C00H C 0.1695(12) 0.4082(3) 0.2692(5) 0.054(3) Uani 1 1 d G . . . .
H00H H 0.090074 0.394982 0.326947 0.065 Uiso 1 1 calc R U . . .
C00C C 0.3996(12) 0.4326(2) 0.3043(4) 0.0367(19) Uani 1 1 d G . . . .
C00A C 0.5183(10) 0.4524(2) 0.2180(5) 0.048(2) Uani 1 1 d G . . . .
H00A H 0.672202 0.468711 0.241432 0.057 Uiso 1 1 calc R U . . .
C00E C 0.4069(12) 0.4478(3) 0.0966(5) 0.052(3) Uani 1 1 d G . . . .
H00E H 0.486327 0.461034 0.038809 0.063 Uiso 1 1 calc R U . . .
C00G C 0.5518(19) 0.3734(3) 0.7741(9) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.672(3) 0.2487(6) 0.7638(11) 0.128(4) Uani 1 1 d G U . . .
H2 H 0.580772 0.254781 0.686115 0.154 Uiso 1 1 calc R U . . .
C00J C 0.810(3) 0.2874(4) 0.8293(14) 0.121(4) Uani 1 1 d G U . . .
C00K C 0.946(3) 0.2784(5) 0.9454(14) 0.128(4) Uani 1 1 d G U . . .
H00K H 1.039047 0.304222 0.989223 0.154 Uiso 1 1 calc R U . . .
C8 C 0.944(3) 0.2307(6) 0.9960(11) 0.136(4) Uani 1 1 d G U . . .
H8 H 1.035003 0.224623 1.073685 0.163 Uiso 1 1 calc R U . . .
C3 C 0.805(3) 0.1920(4) 0.9305(14) 0.134(4) Uani 1 1 d G U . . .
H3 H 0.803845 0.160102 0.964364 0.161 Uiso 1 1 calc R U . . .
C4 C 0.669(3) 0.2010(5) 0.8144(13) 0.133(4) Uani 1 1 d G U . . .
H4 H 0.576728 0.175180 0.770579 0.160 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
S001 C00G 1.698(11) . ?
S001 C00J 1.768(11) . ?
F002 C00G 1.482(11) . ?
O003 H003 0.8200 . ?
O003 C00B 1.382(10) . ?
O1 H1 0.8200 . ?
O1 C00B 1.405(11) . ?
N N008 1.342(10) . ?
N N009 1.321(11) . ?
N C00C 1.409(8) . ?
N006 N009 1.339(10) . ?
N006 C00D 1.336(12) . ?
F007 C00G 1.375(12) . ?
N008 C00D 1.335(11) . ?
C00B C00D 1.514(11) . ?
C00B C00G 1.546(11) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.3900 . ?
C00F C00E 1.3900 . ?
C00I H00I 0.9300 . ?
C00I C00H 1.3900 . ?
C00H H00H 0.9300 . ?
C00H C00C 1.3900 . ?
C00C C00A 1.3900 . ?
C00A H00A 0.9300 . ?
C00A C00E 1.3900 . ?
C00E H00E 0.9300 . ?
C2 H2 0.9300 . ?
C2 C00J 1.3900 . ?
C2 C4 1.3900 . ?
C00J C00K 1.3900 . ?
C00K H00K 0.9300 . ?
C00K C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?

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
C00G S001 C00J 101.4(7) . . ?
C00B O003 H003 109.5 . . ?
C00B O1 H1 109.5 . . ?
N008 N C00C 122.3(6) . . ?
N009 N N008 114.6(6) . . ?
N009 N C00C 123.0(6) . . ?
C00D N006 N009 106.5(7) . . ?
C00D N008 N 100.7(7) . . ?
N N009 N006 105.0(7) . . ?
O003 C00B O1 108.8(7) . . ?
O003 C00B C00D 112.6(7) . . ?
O003 C00B C00G 106.1(6) . . ?
O1 C00B C00D 111.3(6) . . ?
O1 C00B C00G 108.7(7) . . ?
C00D C00B C00G 109.2(7) . . ?
N006 C00D C00B 124.4(7) . . ?
N008 C00D N006 113.1(7) . . ?
N008 C00D C00B 122.5(7) . . ?
C00I C00F H00F 120.0 . . ?
C00I C00F C00E 120.0 . . ?
C00E C00F H00F 120.0 . . ?
C00F C00I H00I 120.0 . . ?
C00H C00I C00F 120.0 . . ?
C00H C00I H00I 120.0 . . ?
C00I C00H H00H 120.0 . . ?
C00I C00H C00C 120.0 . . ?
C00C C00H H00H 120.0 . . ?
C00H C00C N 120.4(4) . . ?
C00A C00C N 119.6(4) . . ?
C00A C00C C00H 120.0 . . ?
C00C C00A H00A 120.0 . . ?
C00C C00A C00E 120.0 . . ?
C00E C00A H00A 120.0 . . ?
C00F C00E H00E 120.0 . . ?
C00A C00E C00F 120.0 . . ?
C00A C00E H00E 120.0 . . ?
F002 C00G S001 103.6(6) . . ?
F002 C00G C00B 115.1(8) . . ?
F007 C00G S001 111.3(7) . . ?
F007 C00G F002 106.4(8) . . ?
F007 C00G C00B 107.3(7) . . ?
C00B C00G S001 113.0(7) . . ?
C00J C2 H2 120.0 . . ?
C00J C2 C4 120.0 . . ?
C4 C2 H2 120.0 . . ?
C2 C00J S001 122.5(9) . . ?
C00K C00J S001 117.4(9) . . ?
C00K C00J C2 120.0 . . ?
C00J C00K H00K 120.0 . . ?
C8 C00K C00J 120.0 . . ?
C8 C00K H00K 120.0 . . ?
C00K C8 H8 120.0 . . ?
C00K C8 C3 120.0 . . ?
C3 C8 H8 120.0 . . ?
C8 C3 H3 120.0 . . ?
C4 C3 C8 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C4 H4 120.0 . . ?
C3 C4 C2 120.0 . . ?
C3 C4 H4 120.0 . . ?

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
S001 C00J C00K C8 -176.9(14) . . . . ?
O003 C00B C00D N006 24.3(11) . . . . ?
O003 C00B C00D N008 -157.8(7) . . . . ?
O003 C00B C00G S001 -62.8(8) . . . . ?
O003 C00B C00G F002 56.0(10) . . . . ?
O003 C00B C00G F007 174.2(8) . . . . ?
O1 C00B C00D N006 146.8(7) . . . . ?
O1 C00B C00D N008 -35.3(10) . . . . ?
O1 C00B C00G S001 -179.6(6) . . . . ?
O1 C00B C00G F002 -60.9(9) . . . . ?
O1 C00B C00G F007 57.3(9) . . . . ?
N N008 C00D N006 -0.8(9) . . . . ?
N N008 C00D C00B -178.8(7) . . . . ?
N C00C C00A C00E 179.7(6) . . . . ?
N008 N N009 N006 0.7(9) . . . . ?
N008 N C00C C00H -15.7(9) . . . . ?
N008 N C00C C00A 164.6(6) . . . . ?
N009 N N008 C00D 0.0(9) . . . . ?
N009 N C00C C00H 161.1(6) . . . . ?
N009 N C00C C00A -18.6(10) . . . . ?
N009 N006 C00D N008 1.2(9) . . . . ?
N009 N006 C00D C00B 179.2(7) . . . . ?
C00D N006 N009 N -1.1(9) . . . . ?
C00D C00B C00G S001 58.8(8) . . . . ?
C00D C00B C00G F002 177.5(7) . . . . ?
C00D C00B C00G F007 -64.2(10) . . . . ?
C00F C00I C00H C00C 0.0 . . . . ?
C00I C00F C00E C00A 0.0 . . . . ?
C00I C00H C00C N -179.7(6) . . . . ?
C00I C00H C00C C00A 0.0 . . . . ?
C00H C00C C00A C00E 0.0 . . . . ?
C00C N N008 C00D 177.1(7) . . . . ?
C00C N N009 N006 -176.4(7) . . . . ?
C00C C00A C00E C00F 0.0 . . . . ?
C00E C00F C00I C00H 0.0 . . . . ?
C00G S001 C00J C2 77.0(11) . . . . ?
C00G S001 C00J C00K -106.2(9) . . . . ?
C00G C00B C00D N006 -93.2(9) . . . . ?
C00G C00B C00D N008 84.7(9) . . . . ?
C2 C00J C00K C8 0.0 . . . . ?
C00J S001 C00G F002 48.3(8) . . . . ?
C00J S001 C00G F007 -65.7(9) . . . . ?
C00J S001 C00G C00B 173.5(8) . . . . ?
C00J C2 C4 C3 0.0 . . . . ?
C00J C00K C8 C3 0.0 . . . . ?
C00K C8 C3 C4 0.0 . . . . ?
C8 C3 C4 C2 0.0 . . . . ?
C4 C2 C00J S001 176.7(14) . . . . ?
C4 C2 C00J C00K 0.0 . . . . ?

_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 1.048
_oxdiff_exptl_absorpt_empirical_full_min 0.942
####################################################################### 
# 
# 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_shs
_database_code_depnum_ccdc_archive 'CCDC 2116301'
loop_
_audit_author_name
_audit_author_address
shihongsong
;Tianjin University
China
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 Br F2 N4 O S'
_chemical_formula_weight         413.25

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   15.5290(10)
_cell_length_b                   10.7691(7)
_cell_length_c                   9.7943(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.839(5)
_cell_angle_gamma                90
_cell_volume                     1632.10(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    2.678
_shelx_estimated_absorpt_T_min   0.429
_shelx_estimated_absorpt_T_max   0.511
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12938
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.817
_diffrn_reflns_theta_max         29.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3856
_reflns_number_gt                2624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+1.5997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br01 Br 0.85049(2) 0.81041(4) 0.32484(4) 0.06063(15) Uani 1 1 d . . . . .
S002 S 0.23582(5) 0.73228(9) 0.93327(8) 0.0478(2) Uani 1 1 d . . . . .
F003 F 0.32655(12) 0.78609(18) 0.72745(17) 0.0513(5) Uani 1 1 d . . . . .
F004 F 0.31331(12) 0.58990(17) 0.7663(2) 0.0572(5) Uani 1 1 d . . . . .
O005 O 0.42898(15) 0.82318(19) 0.9689(2) 0.0466(5) Uani 1 1 d . . . . .
H005 H 0.440918 0.870071 0.907277 0.070 Uiso 1 1 calc R U . . .
N006 N 0.57517(15) 0.6524(2) 0.6924(2) 0.0325(5) Uani 1 1 d . . . . .
N007 N 0.52757(15) 0.7327(2) 0.7565(2) 0.0344(6) Uani 1 1 d . . . . .
N008 N 0.55888(19) 0.5351(2) 0.7215(3) 0.0489(7) Uani 1 1 d . . . . .
N009 N 0.49871(19) 0.5376(2) 0.8090(3) 0.0507(7) Uani 1 1 d . . . . .
C00A C 0.48062(18) 0.6582(2) 0.8275(3) 0.0325(6) Uani 1 1 d . . . . .
C00B C 0.41178(19) 0.7032(2) 0.9146(3) 0.0332(6) Uani 1 1 d . . . . .
H00B H 0.408948 0.645458 0.991433 0.040 Uiso 1 1 calc R U . . .
C00C C 0.63837(18) 0.6892(3) 0.6014(3) 0.0340(6) Uani 1 1 d . . . . .
C00D C 0.3244(2) 0.7015(3) 0.8305(3) 0.0355(7) Uani 1 1 d . . . . .
C00E C 0.6521(2) 0.8144(3) 0.5826(3) 0.0404(7) Uani 1 1 d . . . . .
H00E H 0.620067 0.873268 0.625870 0.049 Uiso 1 1 calc R U . . .
C00F C 0.1492(2) 0.7089(3) 0.8044(3) 0.0424(8) Uani 1 1 d . . . . .
C00G C 0.7147(2) 0.8503(3) 0.4980(3) 0.0445(8) Uani 1 1 d . . . . .
H00G H 0.724965 0.934139 0.483441 0.053 Uiso 1 1 calc R U . . .
C00H C 0.7617(2) 0.7615(3) 0.4355(3) 0.0412(7) Uani 1 1 d . . . . .
C00I C 0.6833(2) 0.6003(3) 0.5360(3) 0.0477(8) Uani 1 1 d . . . . .
H00I H 0.671786 0.516495 0.548027 0.057 Uiso 1 1 calc R U . . .
C00J C 0.1140(2) 0.5919(4) 0.7839(4) 0.0554(9) Uani 1 1 d . . . . .
H00J H 0.135893 0.525567 0.836824 0.067 Uiso 1 1 calc R U . . .
C00K C 0.1158(2) 0.8076(4) 0.7279(4) 0.0573(9) Uani 1 1 d . . . . .
H00K H 0.138341 0.886992 0.742186 0.069 Uiso 1 1 calc R U . . .
C00L C 0.7457(2) 0.6370(3) 0.4523(4) 0.0505(8) Uani 1 1 d . . . . .
H00L H 0.776777 0.577962 0.407447 0.061 Uiso 1 1 calc R U . . .
C00M C 0.0465(3) 0.5728(5) 0.6854(5) 0.0724(12) Uani 1 1 d . . . . .
H00M H 0.023387 0.493720 0.671588 0.087 Uiso 1 1 calc R U . . .
C00N C 0.0138(3) 0.6696(5) 0.6084(4) 0.0777(14) Uani 1 1 d . . . . .
H00N H -0.031608 0.656481 0.541826 0.093 Uiso 1 1 calc R U . . .
C00O C 0.0475(3) 0.7865(5) 0.6283(4) 0.0722(13) Uani 1 1 d . . . . .
H00O H 0.024740 0.852190 0.575217 0.087 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
Br01 C00H 1.899(3) . ?
S002 C00F 1.783(3) . ?
S002 C00D 1.802(3) . ?
F003 C00D 1.362(3) . ?
F004 C00D 1.361(3) . ?
O005 C00B 1.414(3) . ?
O005 H005 0.8200 . ?
N006 N008 1.324(3) . ?
N006 N007 1.329(3) . ?
N006 C00C 1.436(4) . ?
N007 C00A 1.321(4) . ?
N008 N009 1.321(4) . ?
N009 C00A 1.344(4) . ?
C00A C00B 1.503(4) . ?
C00B C00D 1.527(4) . ?
C00B H00B 0.9800 . ?
C00C C00I 1.374(4) . ?
C00C C00E 1.380(4) . ?
C00E C00G 1.384(4) . ?
C00E H00E 0.9300 . ?
C00F C00K 1.376(5) . ?
C00F C00J 1.382(5) . ?
C00G C00H 1.378(5) . ?
C00G H00G 0.9300 . ?
C00H C00L 1.376(5) . ?
C00I C00L 1.379(4) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.378(5) . ?
C00J H00J 0.9300 . ?
C00K C00O 1.398(6) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M C00N 1.360(6) . ?
C00M H00M 0.9300 . ?
C00N C00O 1.370(6) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?

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
C00F S002 C00D 98.32(13) . . ?
C00B O005 H005 109.5 . . ?
N008 N006 N007 113.3(2) . . ?
N008 N006 C00C 123.4(2) . . ?
N007 N006 C00C 123.4(2) . . ?
C00A N007 N006 101.9(2) . . ?
N009 N008 N006 106.2(2) . . ?
N008 N009 C00A 105.9(2) . . ?
N007 C00A N009 112.7(3) . . ?
N007 C00A C00B 123.6(2) . . ?
N009 C00A C00B 123.7(2) . . ?
O005 C00B C00A 112.8(2) . . ?
O005 C00B C00D 110.2(2) . . ?
C00A C00B C00D 109.4(2) . . ?
O005 C00B H00B 108.1 . . ?
C00A C00B H00B 108.1 . . ?
C00D C00B H00B 108.1 . . ?
C00I C00C C00E 121.9(3) . . ?
C00I C00C N006 119.9(3) . . ?
C00E C00C N006 118.3(2) . . ?
F004 C00D F003 105.0(2) . . ?
F004 C00D C00B 109.4(2) . . ?
F003 C00D C00B 108.4(2) . . ?
F004 C00D S002 110.3(2) . . ?
F003 C00D S002 111.0(2) . . ?
C00B C00D S002 112.46(19) . . ?
C00C C00E C00G 118.5(3) . . ?
C00C C00E H00E 120.8 . . ?
C00G C00E H00E 120.8 . . ?
C00K C00F C00J 119.9(3) . . ?
C00K C00F S002 120.2(3) . . ?
C00J C00F S002 119.8(3) . . ?
C00H C00G C00E 119.8(3) . . ?
C00H C00G H00G 120.1 . . ?
C00E C00G H00G 120.1 . . ?
C00L C00H C00G 121.1(3) . . ?
C00L C00H Br01 119.0(2) . . ?
C00G C00H Br01 119.9(2) . . ?
C00C C00I C00L 119.2(3) . . ?
C00C C00I H00I 120.4 . . ?
C00L C00I H00I 120.4 . . ?
C00M C00J C00F 120.4(4) . . ?
C00M C00J H00J 119.8 . . ?
C00F C00J H00J 119.8 . . ?
C00F C00K C00O 118.9(4) . . ?
C00F C00K H00K 120.6 . . ?
C00O C00K H00K 120.6 . . ?
C00H C00L C00I 119.5(3) . . ?
C00H C00L H00L 120.2 . . ?
C00I C00L H00L 120.2 . . ?
C00N C00M C00J 120.0(4) . . ?
C00N C00M H00M 120.0 . . ?
C00J C00M H00M 120.0 . . ?
C00M C00N C00O 120.3(4) . . ?
C00M C00N H00N 119.8 . . ?
C00O C00N H00N 119.8 . . ?
C00N C00O C00K 120.5(4) . . ?
C00N C00O H00O 119.8 . . ?
C00K C00O H00O 119.8 . . ?

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
N008 N006 N007 C00A 0.0(3) . . . . ?
C00C N006 N007 C00A -179.5(3) . . . . ?
N007 N006 N008 N009 -0.5(4) . . . . ?
C00C N006 N008 N009 179.1(3) . . . . ?
N006 N008 N009 C00A 0.7(4) . . . . ?
N006 N007 C00A N009 0.4(3) . . . . ?
N006 N007 C00A C00B -177.1(3) . . . . ?
N008 N009 C00A N007 -0.7(4) . . . . ?
N008 N009 C00A C00B 176.8(3) . . . . ?
N007 C00A C00B O005 -29.8(4) . . . . ?
N009 C00A C00B O005 153.0(3) . . . . ?
N007 C00A C00B C00D 93.2(3) . . . . ?
N009 C00A C00B C00D -84.0(3) . . . . ?
N008 N006 C00C C00I 2.3(4) . . . . ?
N007 N006 C00C C00I -178.2(3) . . . . ?
N008 N006 C00C C00E -177.6(3) . . . . ?
N007 N006 C00C C00E 1.9(4) . . . . ?
O005 C00B C00D F004 173.1(2) . . . . ?
C00A C00B C00D F004 48.5(3) . . . . ?
O005 C00B C00D F003 59.1(3) . . . . ?
C00A C00B C00D F003 -65.4(3) . . . . ?
O005 C00B C00D S002 -64.0(3) . . . . ?
C00A C00B C00D S002 171.51(19) . . . . ?
C00F S002 C00D F004 -52.8(2) . . . . ?
C00F S002 C00D F003 63.1(2) . . . . ?
C00F S002 C00D C00B -175.3(2) . . . . ?
C00I C00C C00E C00G -1.7(5) . . . . ?
N006 C00C C00E C00G 178.2(3) . . . . ?
C00D S002 C00F C00K -92.4(3) . . . . ?
C00D S002 C00F C00J 89.4(3) . . . . ?
C00C C00E C00G C00H -0.3(5) . . . . ?
C00E C00G C00H C00L 2.1(5) . . . . ?
C00E C00G C00H Br01 -177.7(2) . . . . ?
C00E C00C C00I C00L 1.9(5) . . . . ?
N006 C00C C00I C00L -178.0(3) . . . . ?
C00K C00F C00J C00M 1.2(5) . . . . ?
S002 C00F C00J C00M 179.5(3) . . . . ?
C00J C00F C00K C00O -1.3(5) . . . . ?
S002 C00F C00K C00O -179.5(3) . . . . ?
C00G C00H C00L C00I -1.8(5) . . . . ?
Br01 C00H C00L C00I 177.9(3) . . . . ?
C00C C00I C00L C00H -0.1(5) . . . . ?
C00F C00J C00M C00N -0.5(6) . . . . ?
C00J C00M C00N C00O -0.1(6) . . . . ?
C00M C00N C00O C00K 0.0(6) . . . . ?
C00F C00K C00O C00N 0.7(6) . . . . ?

_refine_diff_density_max         0.914
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_shs-2
_database_code_depnum_ccdc_archive 'CCDC 2116304'
loop_
_audit_author_name
_audit_author_address
shihongsong
;Tianjin University
China
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_audit_creation_date             2021-05-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br F3 N4 S'
_chemical_formula_sum            'C15 H10 Br F3 N4 S'
_chemical_formula_weight         415.24
_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      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                   10.1584(16)
_cell_length_b                   4.7541(7)
_cell_length_c                   34.462(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.312(7)
_cell_angle_gamma                90
_cell_volume                     1654.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.41
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.485
_exptl_absorpt_coefficient_mu    2.646
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5765
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0836 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.7729.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            30213
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.039
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1762
_reflns_number_total             2932
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.3289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C2(H2), C15(H15), C12(H12), C3(H3), C4(H4), C6(H6), C5(H5)
;
_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 0.85534(4) 1.37454(9) 0.42711(2) 0.1050(2) Uani 1 1 d . . . . .
S1 S 0.65635(9) 0.59526(16) 0.68854(2) 0.0751(3) Uani 1 1 d . . . . .
F2 F 0.93577(16) 0.6038(3) 0.66965(5) 0.0799(5) Uani 1 1 d . . . . .
F3 F 0.93883(16) 0.2181(4) 0.63810(5) 0.0794(5) Uani 1 1 d . . . . .
F1 F 0.90627(19) 0.2126(4) 0.69826(5) 0.0896(6) Uani 1 1 d . . . . .
N2 N 0.6899(2) 0.6854(5) 0.56063(7) 0.0525(6) Uani 1 1 d . . . . .
N1 N 0.7596(2) 0.6721(4) 0.59568(6) 0.0539(6) Uani 1 1 d . . . . .
N4 N 0.5944(2) 0.3641(5) 0.58927(8) 0.0690(7) Uani 1 1 d . . . . .
N3 N 0.5908(2) 0.5032(6) 0.55629(8) 0.0708(7) Uani 1 1 d . . . . .
C9 C 0.6965(3) 0.4713(6) 0.61257(8) 0.0482(7) Uani 1 1 d . . . . .
C10 C 0.7249(3) 0.8609(6) 0.52979(8) 0.0506(7) Uani 1 1 d . . . . .
C7 C 0.7307(3) 0.3726(5) 0.65341(8) 0.0532(7) Uani 1 1 d . . . . .
H7 H 0.693892 0.183135 0.655246 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8773(3) 0.3528(6) 0.66494(9) 0.0635(8) Uani 1 1 d . . . . .
C11 C 0.8310(3) 1.0378(6) 0.53647(8) 0.0629(8) Uani 1 1 d . . . . .
H11 H 0.877761 1.051582 0.561148 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7977(3) 1.1756(6) 0.46960(9) 0.0657(8) Uani 1 1 d . . . . .
C14 C 0.6910(3) 1.0021(7) 0.46336(9) 0.0726(9) Uani 1 1 d . . . . .
H14 H 0.643554 0.991437 0.438740 0.087 Uiso 1 1 calc R U . . .
C2 C 0.5035(3) 0.2332(7) 0.72507(9) 0.0713(9) Uani 1 1 d . . . . .
H2 H 0.575974 0.219530 0.743981 0.086 Uiso 1 1 calc R U . . .
C1 C 0.5104(3) 0.4024(6) 0.69323(9) 0.0620(8) Uani 1 1 d . . . . .
C15 C 0.6534(3) 0.8427(6) 0.49354(9) 0.0692(8) Uani 1 1 d . . . . .
H15 H 0.580437 0.723863 0.489525 0.083 Uiso 1 1 calc R U . . .
C12 C 0.8666(3) 1.1939(7) 0.50604(9) 0.0776(9) Uani 1 1 d . . . . .
H12 H 0.938883 1.314672 0.510096 0.093 Uiso 1 1 calc R U . . .
C3 C 0.3895(4) 0.0823(7) 0.72932(11) 0.0908(11) Uani 1 1 d . . . . .
H3 H 0.385578 -0.032246 0.751040 0.109 Uiso 1 1 calc R U . . .
C4 C 0.2838(4) 0.1011(9) 0.70194(13) 0.0995(12) Uani 1 1 d . . . . .
H4 H 0.207199 -0.000996 0.704607 0.119 Uiso 1 1 calc R U . . .
C6 C 0.4026(4) 0.4225(9) 0.66606(11) 0.1009(13) Uani 1 1 d . . . . .
H6 H 0.405434 0.539434 0.644533 0.121 Uiso 1 1 calc R U . . .
C5 C 0.2906(4) 0.2720(11) 0.67025(12) 0.1196(15) Uani 1 1 d . . . . .
H5 H 0.218107 0.285699 0.651362 0.144 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
Br1 C13 1.889(3) . ?
S1 C7 1.833(3) . ?
S1 C1 1.766(3) . ?
F2 C8 1.335(3) . ?
F3 C8 1.335(3) . ?
F1 C8 1.332(3) . ?
N2 N1 1.333(3) . ?
N2 N3 1.324(3) . ?
N2 C10 1.426(3) . ?
N1 C9 1.320(3) . ?
N4 N3 1.312(3) . ?
N4 C9 1.341(3) . ?
C9 C7 1.488(4) . ?
C10 C11 1.367(4) . ?
C10 C15 1.377(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.501(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C13 C14 1.360(4) . ?
C13 C12 1.372(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.368(4) . ?
C2 C3 1.384(4) . ?
C1 C6 1.364(4) . ?
C15 H15 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.353(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.365(5) . ?
C5 H5 0.9300 . ?

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
C1 S1 C7 99.89(13) . . ?
N1 N2 C10 123.5(2) . . ?
N3 N2 N1 113.1(2) . . ?
N3 N2 C10 123.2(2) . . ?
C9 N1 N2 101.5(2) . . ?
N3 N4 C9 105.9(2) . . ?
N4 N3 N2 106.5(2) . . ?
N1 C9 N4 113.1(2) . . ?
N1 C9 C7 124.8(2) . . ?
N4 C9 C7 122.1(3) . . ?
C11 C10 N2 119.4(2) . . ?
C11 C10 C15 121.3(3) . . ?
C15 C10 N2 119.3(3) . . ?
S1 C7 H7 107.5 . . ?
C9 C7 S1 111.86(18) . . ?
C9 C7 H7 107.5 . . ?
C9 C7 C8 113.1(2) . . ?
C8 C7 S1 109.3(2) . . ?
C8 C7 H7 107.5 . . ?
F2 C8 C7 113.0(2) . . ?
F3 C8 F2 106.1(3) . . ?
F3 C8 C7 111.9(2) . . ?
F1 C8 F2 106.8(2) . . ?
F1 C8 F3 106.3(2) . . ?
F1 C8 C7 112.2(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11 120.8 . . ?
C14 C13 Br1 119.4(2) . . ?
C14 C13 C12 120.1(3) . . ?
C12 C13 Br1 120.5(3) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C1 S1 119.7(3) . . ?
C6 C1 S1 121.3(3) . . ?
C6 C1 C2 118.9(3) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 C10 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C1 C6 H6 119.8 . . ?
C1 C6 C5 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?

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 C13 C14 C15 175.8(2) . . . . ?
Br1 C13 C12 C11 -175.9(2) . . . . ?
S1 C7 C8 F2 -53.6(3) . . . . ?
S1 C7 C8 F3 -173.26(19) . . . . ?
S1 C7 C8 F1 67.3(3) . . . . ?
S1 C1 C6 C5 -179.9(3) . . . . ?
N2 N1 C9 N4 0.6(3) . . . . ?
N2 N1 C9 C7 -178.3(2) . . . . ?
N2 C10 C11 C12 176.9(3) . . . . ?
N2 C10 C15 C14 -177.0(3) . . . . ?
N1 N2 N3 N4 -0.1(3) . . . . ?
N1 N2 C10 C11 -3.7(4) . . . . ?
N1 N2 C10 C15 174.5(2) . . . . ?
N1 C9 C7 S1 83.7(3) . . . . ?
N1 C9 C7 C8 -40.2(4) . . . . ?
N4 C9 C7 S1 -95.1(3) . . . . ?
N4 C9 C7 C8 141.0(3) . . . . ?
N3 N2 N1 C9 -0.3(3) . . . . ?
N3 N2 C10 C11 -178.2(3) . . . . ?
N3 N2 C10 C15 -0.1(4) . . . . ?
N3 N4 C9 N1 -0.7(3) . . . . ?
N3 N4 C9 C7 178.2(2) . . . . ?
C9 N4 N3 N2 0.4(3) . . . . ?
C9 C7 C8 F2 71.7(3) . . . . ?
C9 C7 C8 F3 -48.0(3) . . . . ?
C9 C7 C8 F1 -167.4(2) . . . . ?
C10 N2 N1 C9 -175.3(2) . . . . ?
C10 N2 N3 N4 175.0(2) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C7 S1 C1 C2 101.2(2) . . . . ?
C7 S1 C1 C6 -80.1(3) . . . . ?
C11 C10 C15 C14 1.2(4) . . . . ?
C13 C14 C15 C10 -0.1(5) . . . . ?
C14 C13 C12 C11 0.7(5) . . . . ?
C2 C1 C6 C5 -1.2(6) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C1 S1 C7 C9 94.7(2) . . . . ?
C1 S1 C7 C8 -139.3(2) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C5 C4 0.8(7) . . . . ?
C15 C10 C11 C12 -1.2(4) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C3 C2 C1 S1 179.5(2) . . . . ?
C3 C2 C1 C6 0.8(5) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
