# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2104187'
loop_
_audit_author_name
_audit_author_address
Yue
;Nanjing University
China
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;
_audit_creation_date             2021-08-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 Br F3 N O3 S'
_chemical_formula_sum            'C17 H11 Br F3 N O3 S'
_chemical_formula_weight         446.24
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.868(5)
_cell_length_b                   12.831(4)
_cell_length_c                   7.106(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.222(13)
_cell_angle_gamma                90
_cell_volume                     1717.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.375
_cell_measurement_theta_min      2.683
_shelx_estimated_absorpt_T_max   0.784
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    2.563
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1433 before and 0.0690 after correction.
The Ratio of minimum to maximum transmission is 0.8067.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9748
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.663
_diffrn_reflns_theta_min         1.920
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2896
_reflns_number_total             3813
_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 1.5 (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  (Sheldrick, 2015)'
_refine_diff_density_max         0.995
_refine_diff_density_min         -1.464
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.062
_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)+(0.1596P)²+3.4299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2603
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 2A
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_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 0.42807(4) 0.14533(5) 0.59875(9) 0.0499(3) Uani 1 1 d . . . . .
S1 S 0.67498(9) 0.50975(12) 0.3469(2) 0.0444(4) Uani 1 1 d . . . . .
F1 F 0.8115(2) 0.5483(4) 0.3494(8) 0.0677(13) Uani 1 1 d . . . . .
F2 F 0.7423(3) 0.6653(4) 0.2320(9) 0.0867(19) Uani 1 1 d . . . . .
F3 F 0.7573(3) 0.6442(4) 0.5293(8) 0.0799(17) Uani 1 1 d . . . . .
O1 O 0.7545(2) 0.3466(3) 0.4541(6) 0.0389(9) Uani 1 1 d . . . . .
O2 O 0.6977(3) 0.5012(3) 0.8218(6) 0.0462(10) Uani 1 1 d . . . . .
O3 O 0.8657(3) 0.3064(4) 0.5545(8) 0.0574(13) Uani 1 1 d . . . . .
N1 N 0.7945(3) 0.4120(4) 0.7319(7) 0.0367(11) Uani 1 1 d . . . . .
C1 C 0.5110(3) 0.2264(4) 0.5758(8) 0.0360(11) Uani 1 1 d . U . . .
C2 C 0.5748(3) 0.1772(4) 0.5418(8) 0.0343(11) Uani 1 1 d . U . . .
H2 H 0.577000 0.103487 0.530650 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6350(3) 0.2372(4) 0.5244(7) 0.0334(12) Uani 1 1 d . . . . .
H3 H 0.678989 0.204618 0.502164 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6314(3) 0.3451(4) 0.5393(7) 0.0293(11) Uani 1 1 d . . . . .
C5 C 0.5678(3) 0.3926(4) 0.5742(8) 0.0318(11) Uani 1 1 d . . . . .
H5 H 0.565363 0.466274 0.584859 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5080(3) 0.3334(4) 0.5935(8) 0.0345(11) Uani 1 1 d . . . . .
H6 H 0.464463 0.366180 0.619204 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6972(3) 0.4096(4) 0.5210(8) 0.0326(11) Uani 1 1 d . . . . .
C8 C 0.7276(3) 0.4493(4) 0.7113(8) 0.0318(11) Uani 1 1 d . . . . .
C9 C 0.8113(3) 0.3494(4) 0.5770(9) 0.0371(13) Uani 1 1 d . . . . .
C10 C 0.7500(4) 0.5958(5) 0.3670(10) 0.0482(16) Uani 1 1 d . . . . .
C11 C 0.8463(3) 0.4322(5) 0.8896(9) 0.0413(13) Uani 1 1 d . . . . .
H11A H 0.872971 0.367391 0.920478 0.050 Uiso 1 1 calc R U . . .
H11B H 0.820782 0.452585 1.001938 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8978(3) 0.5174(5) 0.8438(8) 0.0391(13) Uani 1 1 d . . . . .
C13 C 0.8821(4) 0.6209(5) 0.8770(11) 0.0542(17) Uani 1 1 d . . . . .
H13 H 0.838583 0.638581 0.929981 0.065 Uiso 1 1 calc R U . . .
C14 C 0.9292(5) 0.6989(6) 0.8339(13) 0.069(2) Uani 1 1 d . . . . .
H14 H 0.918025 0.769933 0.856021 0.083 Uiso 1 1 calc R U . . .
C15 C 0.9922(5) 0.6724(6) 0.7586(12) 0.064(2) Uani 1 1 d . . . . .
H15 H 1.025237 0.725035 0.729378 0.076 Uiso 1 1 calc R U . . .
C16 C 1.0070(4) 0.5721(7) 0.7264(12) 0.061(2) Uani 1 1 d . . . . .
H16 H 1.050529 0.554930 0.672882 0.074 Uiso 1 1 calc R U . . .
C17 C 0.9619(4) 0.4945(6) 0.7679(11) 0.0528(17) Uani 1 1 d . . . . .
H17 H 0.974226 0.424108 0.744724 0.063 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 C1 1.893(6) . ?
S1 C7 1.817(6) . ?
S1 C10 1.794(7) . ?
F1 C10 1.323(9) . ?
F2 C10 1.312(8) . ?
F3 C10 1.311(9) . ?
O1 C7 1.450(7) . ?
O1 C9 1.345(8) . ?
O2 C8 1.196(7) . ?
O3 C9 1.185(8) . ?
N1 C8 1.350(7) . ?
N1 C9 1.413(8) . ?
N1 C11 1.467(7) . ?
C1 C2 1.393(9) . ?
C1 C6 1.380(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(7) . ?
C4 C5 1.381(8) . ?
C4 C7 1.504(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.526(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.511(9) . ?
C12 C13 1.384(9) . ?
C12 C17 1.382(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.338(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.354(11) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S1 C7 103.3(3) . . ?
C9 O1 C7 110.7(4) . . ?
C8 N1 C9 111.4(5) . . ?
C8 N1 C11 126.8(5) . . ?
C9 N1 C11 121.8(5) . . ?
C2 C1 Br1 119.5(4) . . ?
C6 C1 Br1 120.0(5) . . ?
C6 C1 C2 120.4(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C7 119.8(5) . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 C7 120.2(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(5) . . ?
C5 C6 H6 119.9 . . ?
O1 C7 S1 108.6(4) . . ?
O1 C7 C4 110.8(4) . . ?
O1 C7 C8 103.1(4) . . ?
C4 C7 S1 106.7(4) . . ?
C4 C7 C8 112.2(5) . . ?
C8 C7 S1 115.4(4) . . ?
O2 C8 N1 126.8(5) . . ?
O2 C8 C7 126.8(5) . . ?
N1 C8 C7 106.3(5) . . ?
O1 C9 N1 108.5(5) . . ?
O3 C9 O1 124.4(6) . . ?
O3 C9 N1 127.1(6) . . ?
F1 C10 S1 113.7(5) . . ?
F2 C10 S1 107.8(5) . . ?
F2 C10 F1 107.8(6) . . ?
F3 C10 S1 113.9(5) . . ?
F3 C10 F1 104.6(6) . . ?
F3 C10 F2 108.9(6) . . ?
N1 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
N1 C11 C12 111.8(5) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 120.8(7) . . ?
C17 C12 C11 121.2(6) . . ?
C17 C12 C13 118.0(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(8) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.1(8) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(8) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.0 . . ?
C15 C16 C17 122.0(9) . . ?
C17 C16 H16 119.0 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.3(7) . . ?
C16 C17 H17 119.9 . . ?

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 C3 179.7(4) . . . . ?
Br1 C1 C6 C5 -179.0(4) . . . . ?
S1 C7 C8 O2 65.2(7) . . . . ?
S1 C7 C8 N1 -116.2(4) . . . . ?
O1 C7 C8 O2 -176.6(6) . . . . ?
O1 C7 C8 N1 2.0(5) . . . . ?
N1 C11 C12 C13 87.8(8) . . . . ?
N1 C11 C12 C17 -92.2(7) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C2 C1 C6 C5 1.2(8) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C2 C3 C4 C7 179.7(5) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C3 C4 C7 S1 128.7(5) . . . . ?
C3 C4 C7 O1 10.7(7) . . . . ?
C3 C4 C7 C8 -104.0(6) . . . . ?
C4 C5 C6 C1 -0.8(8) . . . . ?
C4 C7 C8 O2 -57.3(8) . . . . ?
C4 C7 C8 N1 121.3(5) . . . . ?
C5 C4 C7 S1 -52.5(6) . . . . ?
C5 C4 C7 O1 -170.5(5) . . . . ?
C5 C4 C7 C8 74.8(6) . . . . ?
C6 C1 C2 C3 -0.6(8) . . . . ?
C7 S1 C10 F1 54.0(6) . . . . ?
C7 S1 C10 F2 173.4(5) . . . . ?
C7 S1 C10 F3 -65.7(6) . . . . ?
C7 O1 C9 O3 -178.4(6) . . . . ?
C7 O1 C9 N1 1.2(6) . . . . ?
C7 C4 C5 C6 -179.0(5) . . . . ?
C8 N1 C9 O1 0.3(7) . . . . ?
C8 N1 C9 O3 179.8(6) . . . . ?
C8 N1 C11 C12 -98.3(7) . . . . ?
C9 O1 C7 S1 120.9(4) . . . . ?
C9 O1 C7 C4 -122.2(5) . . . . ?
C9 O1 C7 C8 -2.0(6) . . . . ?
C9 N1 C8 O2 177.2(6) . . . . ?
C9 N1 C8 C7 -1.5(6) . . . . ?
C9 N1 C11 C12 80.7(7) . . . . ?
C10 S1 C7 O1 -70.9(4) . . . . ?
C10 S1 C7 C4 169.7(4) . . . . ?
C10 S1 C7 C8 44.3(5) . . . . ?
C11 N1 C8 O2 -3.7(10) . . . . ?
C11 N1 C8 C7 177.7(5) . . . . ?
C11 N1 C9 O1 -178.9(5) . . . . ?
C11 N1 C9 O3 0.6(10) . . . . ?
C11 C12 C13 C14 -179.6(6) . . . . ?
C11 C12 C17 C16 179.4(7) . . . . ?
C12 C13 C14 C15 -0.5(12) . . . . ?
C13 C12 C17 C16 -0.6(10) . . . . ?
C13 C14 C15 C16 0.6(13) . . . . ?
C14 C15 C16 C17 -0.8(13) . . . . ?
C15 C16 C17 C12 0.8(12) . . . . ?
C17 C12 C13 C14 0.5(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
