# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_11350_tw
_database_code_depnum_ccdc_archive 'CCDC 2022448'
loop_
_audit_author_name
_audit_author_address
'Kejin Yuan'
;Huaxueyuyaoxueyuan,qingdao
China
;
_audit_update_record             
;
2020-08-10 deposited with the CCDC.	2020-10-19 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            'C19 H16 Br F N2 O3 S'
_chemical_formula_weight         451.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.5459(4)
_cell_length_b                   8.94958(15)
_cell_length_c                   14.9499(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.747(3)
_cell_angle_gamma                90
_cell_volume                     1823.62(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8674
_cell_measurement_theta_min      3.2430
_cell_measurement_theta_max      71.1090

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.441
_shelx_estimated_absorpt_T_min   0.618
_shelx_estimated_absorpt_T_max   0.641
_exptl_absorpt_correction_T_min  0.57642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3267
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.242
_diffrn_reflns_theta_max         67.243
_diffrn_reflns_theta_full        67.243
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3267
_reflns_number_gt                3181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3267
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.45042(4) 0.32479(5) 0.71074(4) 0.05436(19) Uani 1 1 d . . . . .
S1 S 0.13534(6) 0.61810(10) 1.16971(6) 0.0373(2) Uani 1 1 d . . . . .
F1 F -0.05485(18) 0.9829(4) 0.7538(2) 0.0648(8) Uani 1 1 d . . . . .
N1 N 0.37069(19) 0.6424(3) 0.9571(2) 0.0314(6) Uani 1 1 d . . . . .
N2 N 0.18846(19) 0.5731(3) 1.1026(2) 0.0330(6) Uani 1 1 d . . . . .
O1 O 0.1323(3) 0.4917(4) 1.2251(3) 0.0631(9) Uani 1 1 d . . . . .
O2 O 0.1754(2) 0.7543(4) 1.2211(2) 0.0589(7) Uani 1 1 d . . . . .
O3 O 0.02269(18) 0.6465(3) 1.0872(2) 0.0425(6) Uani 1 1 d . . . . .
C1 C 0.3887(3) 0.3531(4) 0.7932(3) 0.0343(7) Uani 1 1 d . . . . .
C2 C 0.4037(2) 0.4868(4) 0.8447(3) 0.0341(7) Uani 1 1 d . . . . .
H2 H 0.443667 0.560116 0.839876 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3576(2) 0.5105(3) 0.9043(2) 0.0269(6) Uani 1 1 d . . . . .
C4 C 0.4201(2) 0.7710(4) 0.9433(3) 0.0363(7) Uani 1 1 d . . . . .
H4A H 0.389643 0.800738 0.872204 0.044 Uiso 1 1 calc R U . . .
H4B H 0.488960 0.750038 0.967153 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4073(3) 0.8922(4) 1.0089(3) 0.0404(8) Uani 1 1 d . . . . .
H5A H 0.461960 0.891844 1.077761 0.048 Uiso 1 1 calc R U . . .
H5B H 0.402011 0.990539 0.979329 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3123(3) 0.8485(4) 1.0079(4) 0.0403(8) Uani 1 1 d . . . . .
H6A H 0.255637 0.883877 0.946513 0.048 Uiso 1 1 calc R U . . .
H6B H 0.309834 0.888476 1.066998 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3163(2) 0.6779(3) 1.0110(3) 0.0277(7) Uani 1 1 d . . . . .
H7 H 0.354400 0.645168 1.082101 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2166(2) 0.5956(3) 0.9607(2) 0.0240(6) Uani 1 1 d . . . . .
H8 H 0.179421 0.626652 0.889147 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2394(2) 0.4281(3) 0.9646(3) 0.0317(7) Uani 1 1 d . . . . .
H9A H 0.277433 0.396340 1.035084 0.038 Uiso 1 1 calc R U . . .
H9B H 0.178659 0.371660 0.933515 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2961(2) 0.3984(3) 0.9088(2) 0.0273(6) Uani 1 1 d . . . . .
C11 C 0.2845(2) 0.2661(4) 0.8558(3) 0.0361(7) Uani 1 1 d . . . . .
H11 H 0.244096 0.192270 0.859343 0.043 Uiso 1 1 calc R U . . .
C12 C 0.3306(3) 0.2398(4) 0.7980(3) 0.0412(8) Uani 1 1 d . . . . .
H12 H 0.322838 0.149761 0.763804 0.049 Uiso 1 1 calc R U . . .
C13 C 0.1585(2) 0.6328(3) 1.0135(2) 0.0238(6) Uani 1 1 d . . . . .
C14 C 0.0711(2) 0.7285(3) 0.9646(2) 0.0261(6) Uani 1 1 d . . . . .
C15 C 0.0063(2) 0.7346(3) 1.0041(2) 0.0297(6) Uani 1 1 d . . . . .
C16 C -0.0785(2) 0.8189(3) 0.9606(3) 0.0367(8) Uani 1 1 d . . . . .
H16 H -0.120368 0.819434 0.988686 0.044 Uiso 1 1 calc R U . . .
C17 C -0.1002(2) 0.9027(4) 0.8742(3) 0.0387(7) Uani 1 1 d . . . . .
H17 H -0.157068 0.959948 0.842754 0.046 Uiso 1 1 calc R U . . .
C18 C -0.0354(3) 0.8987(4) 0.8366(3) 0.0391(8) Uani 1 1 d . . . . .
C19 C 0.0483(2) 0.8135(4) 0.8774(3) 0.0341(7) Uani 1 1 d . . . . .
H19 H 0.088928 0.812179 0.847735 0.041 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 1.908(3) . ?
S1 O2 1.416(4) . ?
S1 O1 1.416(3) . ?
S1 O3 1.605(3) . ?
S1 N2 1.628(3) . ?
F1 C18 1.353(4) . ?
N1 C3 1.380(4) . ?
N1 C4 1.452(4) . ?
N1 C7 1.456(4) . ?
N2 C13 1.295(4) . ?
O3 C15 1.388(4) . ?
C1 C2 1.381(5) . ?
C1 C12 1.383(5) . ?
C2 C3 1.402(5) . ?
C3 C10 1.410(4) . ?
C4 C5 1.538(5) . ?
C5 C6 1.522(4) . ?
C6 C7 1.528(4) . ?
C7 C8 1.546(4) . ?
C8 C13 1.496(4) . ?
C8 C9 1.534(4) . ?
C9 C10 1.500(4) . ?
C10 C11 1.387(5) . ?
C11 C12 1.384(5) . ?
C13 C14 1.470(4) . ?
C14 C15 1.392(4) . ?
C14 C19 1.399(5) . ?
C15 C16 1.380(4) . ?
C16 C17 1.387(6) . ?
C17 C18 1.370(5) . ?
C18 C19 1.372(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.0(2) . . ?
O2 S1 O3 108.28(18) . . ?
O1 S1 O3 104.21(18) . . ?
O2 S1 N2 109.00(18) . . ?
O1 S1 N2 109.44(16) . . ?
O3 S1 N2 104.76(14) . . ?
C3 N1 C4 122.6(3) . . ?
C3 N1 C7 122.6(2) . . ?
C4 N1 C7 113.1(2) . . ?
C13 N2 S1 119.6(2) . . ?
C15 O3 S1 116.14(19) . . ?
C2 C1 C12 123.1(3) . . ?
C2 C1 Br1 118.2(3) . . ?
C12 C1 Br1 118.7(3) . . ?
C1 C2 C3 119.0(3) . . ?
N1 C3 C2 120.9(3) . . ?
N1 C3 C10 119.8(3) . . ?
C2 C3 C10 119.3(3) . . ?
N1 C4 C5 103.3(3) . . ?
C6 C5 C4 103.6(3) . . ?
C5 C6 C7 103.3(3) . . ?
N1 C7 C6 103.2(3) . . ?
N1 C7 C8 109.8(2) . . ?
C6 C7 C8 116.4(3) . . ?
C13 C8 C9 112.5(2) . . ?
C13 C8 C7 110.8(2) . . ?
C9 C8 C7 106.8(2) . . ?
C10 C9 C8 109.7(3) . . ?
C11 C10 C3 119.0(3) . . ?
C11 C10 C9 121.3(3) . . ?
C3 C10 C9 119.6(3) . . ?
C12 C11 C10 122.6(3) . . ?
C1 C12 C11 117.1(3) . . ?
N2 C13 C14 122.8(3) . . ?
N2 C13 C8 116.2(2) . . ?
C14 C13 C8 121.0(3) . . ?
C15 C14 C19 117.6(3) . . ?
C15 C14 C13 119.7(3) . . ?
C19 C14 C13 122.7(3) . . ?
C16 C15 O3 117.1(3) . . ?
C16 C15 C14 122.9(3) . . ?
O3 C15 C14 120.0(3) . . ?
C15 C16 C17 119.0(3) . . ?
C18 C17 C16 118.0(3) . . ?
F1 C18 C17 118.4(3) . . ?
F1 C18 C19 117.6(3) . . ?
C17 C18 C19 124.0(3) . . ?
C18 C19 C14 118.5(3) . . ?

_refine_diff_density_max         0.696
_refine_diff_density_min         -0.917
_refine_diff_density_rms         0.077



