# 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_zxb-1_2
_database_code_depnum_ccdc_archive 'CCDC 2014798'
loop_
_audit_author_name
_audit_author_address
'Xiaobao Zeng'
;Nantong University
China
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;
_audit_creation_date             2020-07-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Br N2 O S'
_chemical_formula_sum            'C18 H15 Br N2 O S'
_chemical_formula_weight         387.29
_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'
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                   10.6922(6)
_cell_length_b                   8.9341(8)
_cell_length_c                   17.5905(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.505(6)
_cell_angle_gamma                90
_cell_volume                     1661.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      28.9370
_cell_measurement_theta_min      2.5870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0641
_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       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.926
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  18.00   1.00    5.00    --  -11.59 -99.00 120.00   38
  2  ω     41.00  93.00   1.00    5.00    --   11.74-178.00 120.00   52
  3  ω    -26.00  90.00   1.00    5.00    --   11.74  19.00   0.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0198260000
_diffrn_orient_matrix_UB_12      -0.0196984000
_diffrn_orient_matrix_UB_13      0.0389895000
_diffrn_orient_matrix_UB_21      0.0243594000
_diffrn_orient_matrix_UB_22      -0.0686960000
_diffrn_orient_matrix_UB_23      -0.0118360000
_diffrn_orient_matrix_UB_31      0.0593085000
_diffrn_orient_matrix_UB_32      0.0345145000
_diffrn_orient_matrix_UB_33      -0.0013286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2368
_reflns_number_total             2931
_reflns_odcompleteness_completeness 99.94
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         1.042
_refine_diff_density_min         -1.611
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.072
_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)+(0.0508P)²+0.9953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.59292(4) 0.34200(7) 0.76172(3) 0.0516(2) Uani 1 1 d . . . . .
S1 S 0.13257(9) 0.79059(11) 0.55709(5) 0.0217(3) Uani 1 1 d . . . . .
O1 O 0.0679(2) 0.2806(3) 0.76520(14) 0.0233(6) Uani 1 1 d . . . . .
N1 N 0.1714(2) 0.4168(4) 0.68691(16) 0.0145(7) Uani 1 1 d . . . . .
N2 N 0.0112(3) 1.0437(4) 0.6093(2) 0.0327(9) Uani 1 1 d . . . . .
C1 C 0.3532(3) 0.4534(4) 0.79149(19) 0.0157(8) Uani 1 1 d . . . . .
C2 C 0.2801(3) 0.5402(4) 0.8337(2) 0.0179(8) Uani 1 1 d . . . . .
H2 H 0.192893 0.542931 0.819018 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3331(3) 0.6225(5) 0.8968(2) 0.0215(9) Uani 1 1 d . . . . .
H3 H 0.281817 0.679526 0.923836 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4634(4) 0.6200(5) 0.9198(2) 0.0257(9) Uani 1 1 d . . . . .
H4 H 0.499282 0.674527 0.962582 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5386(3) 0.5367(5) 0.8790(2) 0.0258(9) Uani 1 1 d . . . . .
H5 H 0.625829 0.535089 0.893749 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4839(3) 0.4555(5) 0.8160(2) 0.0222(9) Uani 1 1 d . . . . .
C7 C 0.2936(3) 0.3586(4) 0.7243(2) 0.0169(8) Uani 1 1 d . . . . .
H7A H 0.351148 0.353139 0.686612 0.020 Uiso 1 1 calc R U . . .
H7B H 0.281627 0.257708 0.742323 0.020 Uiso 1 1 calc R U . . .
C8 C 0.1773(3) 0.5217(4) 0.62610(19) 0.0144(8) Uani 1 1 d . . . . .
C9 C 0.1370(3) 0.6606(4) 0.6331(2) 0.0140(8) Uani 1 1 d . . . . .
H9 H 0.110495 0.690159 0.678807 0.017 Uiso 1 1 calc R U . . .
C10 C 0.0597(3) 0.9365(5) 0.5924(2) 0.0215(9) Uani 1 1 d . . . . .
C11 C -0.0618(3) 0.4167(5) 0.6665(2) 0.0222(9) Uani 1 1 d . . . . .
H11A H -0.126890 0.346605 0.674016 0.033 Uiso 1 1 calc R U . . .
H11B H -0.055329 0.422972 0.612719 0.033 Uiso 1 1 calc R U . . .
H11C H -0.082411 0.513443 0.684890 0.033 Uiso 1 1 calc R U . . .
C12 C 0.0625(3) 0.3651(4) 0.7101(2) 0.0161(8) Uani 1 1 d . . . . .
C13 C 0.2275(3) 0.4623(4) 0.55770(19) 0.0152(8) Uani 1 1 d . . . . .
C14 C 0.1884(3) 0.3222(4) 0.5287(2) 0.0194(8) Uani 1 1 d . . . . .
H14 H 0.134758 0.264722 0.553992 0.023 Uiso 1 1 calc R U . . .
C15 C 0.2284(3) 0.2674(5) 0.4627(2) 0.0252(9) Uani 1 1 d . . . . .
H15 H 0.200334 0.174579 0.443305 0.030 Uiso 1 1 calc R U . . .
C16 C 0.3106(3) 0.3511(5) 0.4255(2) 0.0239(10) Uani 1 1 d . . . . .
H16 H 0.337230 0.314783 0.380982 0.029 Uiso 1 1 calc R U . . .
C17 C 0.3522(3) 0.4879(5) 0.4548(2) 0.0204(9) Uani 1 1 d . . . . .
H17 H 0.407424 0.543884 0.430052 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3124(3) 0.5434(4) 0.5211(2) 0.0182(8) Uani 1 1 d . . . . .
H18 H 0.342622 0.635011 0.541064 0.022 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 C6 1.905(4) . ?
S1 C9 1.766(4) . ?
S1 C10 1.684(4) . ?
O1 C12 1.223(4) . ?
N1 C7 1.468(4) . ?
N1 C8 1.430(5) . ?
N1 C12 1.370(4) . ?
N2 C10 1.149(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.400(5) . ?
C1 C7 1.516(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.325(5) . ?
C8 C13 1.486(5) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C12 1.505(5) . ?
C13 C14 1.392(5) . ?
C13 C18 1.391(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(5) . ?
C18 H18 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
C10 S1 C9 101.08(18) . . ?
C8 N1 C7 115.6(3) . . ?
C12 N1 C7 119.1(3) . . ?
C12 N1 C8 125.3(3) . . ?
C2 C1 C6 116.2(3) . . ?
C2 C1 C7 121.5(3) . . ?
C6 C1 C7 122.2(3) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.5(3) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 Br1 119.6(3) . . ?
C5 C6 Br1 117.7(3) . . ?
C5 C6 C1 122.7(3) . . ?
N1 C7 C1 113.3(3) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C1 C7 H7A 108.9 . . ?
C1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C13 115.6(3) . . ?
C9 C8 N1 119.6(3) . . ?
C9 C8 C13 124.8(3) . . ?
S1 C9 H9 119.4 . . ?
C8 C9 S1 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
N2 C10 S1 172.8(4) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
O1 C12 N1 120.1(3) . . ?
O1 C12 C11 121.8(3) . . ?
N1 C12 C11 118.0(3) . . ?
C14 C13 C8 119.5(3) . . ?
C18 C13 C8 121.8(3) . . ?
C18 C13 C14 118.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(4) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(4) . . ?
C17 C18 H18 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
N1 C8 C9 S1 -175.8(2) . . . . ?
N1 C8 C13 C14 43.1(4) . . . . ?
N1 C8 C13 C18 -137.3(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C1 C6 Br1 -179.4(3) . . . . ?
C2 C1 C6 C5 0.9(6) . . . . ?
C2 C1 C7 N1 26.9(5) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 Br1 -180.0(3) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C1 C7 N1 -154.9(3) . . . . ?
C7 N1 C8 C9 -117.1(4) . . . . ?
C7 N1 C8 C13 64.1(4) . . . . ?
C7 N1 C12 O1 5.7(5) . . . . ?
C7 N1 C12 C11 -174.9(3) . . . . ?
C7 C1 C2 C3 177.5(3) . . . . ?
C7 C1 C6 Br1 2.4(5) . . . . ?
C7 C1 C6 C5 -177.4(4) . . . . ?
C8 N1 C7 C1 89.1(4) . . . . ?
C8 N1 C12 O1 -176.6(3) . . . . ?
C8 N1 C12 C11 2.8(5) . . . . ?
C8 C13 C14 C15 176.6(3) . . . . ?
C8 C13 C18 C17 -176.5(3) . . . . ?
C9 C8 C13 C14 -135.6(4) . . . . ?
C9 C8 C13 C18 44.0(5) . . . . ?
C10 S1 C9 C8 173.6(3) . . . . ?
C12 N1 C7 C1 -93.0(4) . . . . ?
C12 N1 C8 C9 65.1(5) . . . . ?
C12 N1 C8 C13 -113.6(4) . . . . ?
C13 C8 C9 S1 2.9(5) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C14 C13 C18 C17 3.1(5) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C16 C17 C18 C13 -1.5(5) . . . . ?
C18 C13 C14 C15 -3.0(5) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.649
