# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_g210507b
_database_code_depnum_ccdc_archive 'CCDC 2083272'
loop_
_audit_author_name
_audit_author_address
xu
;Soochow University
China
;
_audit_update_record             
;
2021-05-12 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Br N2 S'
_chemical_formula_sum            'C15 H11 Br N2 S'
_chemical_formula_weight         331.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O F'
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'
Br Br -0.6763 1.2805 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9320(3)
_cell_length_b                   9.4729(4)
_cell_length_c                   17.8231(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.434(4)
_cell_angle_gamma                90
_cell_volume                     1327.95(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3750
_cell_measurement_temperature    290.45(10)
_cell_measurement_theta_max      77.2120
_cell_measurement_theta_min      4.6210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.575
_diffrn_reflns_theta_min         5.005
_diffrn_ambient_temperature      290.45(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -112.00  -86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -57.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -57.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega -100.00   -8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -77.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega -111.00  -10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9843  -57.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9843 -125.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega  148.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega  122.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   62.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 13 omega   87.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega  148.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   55.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega  137.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -15.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  109.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -15.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -15.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   31.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
 21 omega  101.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 22 omega   88.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 23 omega   95.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega  109.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000  -60.0000 61

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   72.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   88.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -82.0000  104.0000 60

#__ type_ start__ end____ width___ exp.time_
 28 omega  117.00  157.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 29 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -84.0000  -88.1272 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   88.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -180.0000 41
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1063178000
_diffrn_orient_matrix_UB_12      0.1366197000
_diffrn_orient_matrix_UB_13      -0.0074351000
_diffrn_orient_matrix_UB_21      -0.0746002000
_diffrn_orient_matrix_UB_22      -0.0373857000
_diffrn_orient_matrix_UB_23      0.0730657000
_diffrn_orient_matrix_UB_31      0.1463843000
_diffrn_orient_matrix_UB_32      0.0802669000
_diffrn_orient_matrix_UB_33      0.0469210000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2465
_reflns_number_total             2809
_reflns_odcompleteness_completeness 96.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.044
_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)+(0.1110P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
;
_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
Br01 Br 0.68311(5) 0.71205(4) 0.45247(2) 0.04495(19) Uani 1 1 d . . . . .
N003 N 0.1292(3) 0.7970(2) 0.65522(14) 0.0254(5) Uani 1 1 d . . . . .
N004 N -0.1125(4) 0.9534(4) 0.60858(18) 0.0461(7) Uani 1 1 d . . . . .
C005 C 0.2643(3) 0.7788(2) 0.61105(15) 0.0232(5) Uani 1 1 d . . . . .
C006 C -0.0019(3) 0.5745(3) 0.69801(16) 0.0246(5) Uani 1 1 d . . . . .
C007 C 0.3925(3) 0.6780(3) 0.62912(15) 0.0240(5) Uani 1 1 d . . . . .
C008 C 0.1019(3) 0.7059(2) 0.72047(15) 0.0231(5) Uani 1 1 d . . . . .
H008 H 0.0384 0.7617 0.7537 0.028 Uiso 1 1 calc R . . . .
C009 C 0.5188(4) 0.6602(3) 0.58214(16) 0.0288(5) Uani 1 1 d . . . . .
H009 H 0.6039 0.5933 0.5938 0.035 Uiso 1 1 calc R . . . .
C00A C -0.0005(4) 0.8801(3) 0.62943(16) 0.0280(5) Uani 1 1 d . . . . .
C00B C 0.2752(4) 0.6724(3) 0.76492(15) 0.0268(5) Uani 1 1 d . . . . .
H00A H 0.2589 0.6207 0.8104 0.032 Uiso 1 1 calc R . . . .
H00B H 0.3333 0.7600 0.7801 0.032 Uiso 1 1 calc R . . . .
C00C C 0.3937(4) 0.8456(3) 0.50042(16) 0.0303(6) Uani 1 1 d . . . . .
H00C H 0.3955 0.9023 0.4579 0.036 Uiso 1 1 calc R . . . .
C00D C -0.0751(4) 0.5025(3) 0.75362(17) 0.0301(6) Uani 1 1 d . . . . .
H00D H -0.0643 0.5380 0.8026 0.036 Uiso 1 1 calc R . . . .
C00E C 0.5160(4) 0.7429(3) 0.51806(16) 0.0285(6) Uani 1 1 d . . . . .
C00F C -0.0214(4) 0.5214(3) 0.62455(17) 0.0319(6) Uani 1 1 d . . . . .
H00F H 0.0260 0.5690 0.5867 0.038 Uiso 1 1 calc R . . . .
C00G C 0.2685(4) 0.8631(3) 0.54693(16) 0.0289(6) Uani 1 1 d . . . . .
H00G H 0.1857 0.9321 0.5354 0.035 Uiso 1 1 calc R . . . .
C00H C -0.1641(4) 0.3777(3) 0.7366(2) 0.0353(6) Uani 1 1 d . . . . .
H00H H -0.2120 0.3300 0.7742 0.042 Uiso 1 1 calc R . . . .
C00I C -0.1815(4) 0.3247(3) 0.6639(2) 0.0378(7) Uani 1 1 d . . . . .
H00I H -0.2400 0.2406 0.6526 0.045 Uiso 1 1 calc R . . . .
C00J C -0.1117(4) 0.3969(4) 0.6078(2) 0.0387(7) Uani 1 1 d . . . . .
H00J H -0.1252 0.3620 0.5586 0.046 Uiso 1 1 calc R . . . .
S1 S 0.40509(9) 0.56945(7) 0.70970(4) 0.0293(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00E 1.900(3) . ?
N003 C005 1.420(4) . ?
N003 C008 1.486(3) . ?
N003 C00A 1.329(4) . ?
N004 C00A 1.151(4) . ?
C005 C007 1.402(4) . ?
C005 C00G 1.398(4) . ?
C006 C008 1.517(3) . ?
C006 C00D 1.391(4) . ?
C006 C00F 1.393(4) . ?
C007 C009 1.396(4) . ?
C007 S1 1.759(3) . ?
C008 H008 0.9800 . ?
C008 C00B 1.528(4) . ?
C009 H009 0.9300 . ?
C009 C00E 1.383(4) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00B S1 1.801(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.382(5) . ?
C00C C00G 1.383(4) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.390(4) . ?
C00F H00F 0.9300 . ?
C00F C00J 1.391(4) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00I 1.379(5) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.385(5) . ?
C00J H00J 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
C005 N003 C008 124.1(2) . . ?
C00A N003 C005 119.0(2) . . ?
C00A N003 C008 115.5(2) . . ?
C007 C005 N003 122.2(2) . . ?
C00G C005 N003 118.9(2) . . ?
C00G C005 C007 118.9(3) . . ?
C00D C006 C008 118.5(2) . . ?
C00D C006 C00F 119.1(3) . . ?
C00F C006 C008 122.3(2) . . ?
C005 C007 S1 123.3(2) . . ?
C009 C007 C005 120.0(3) . . ?
C009 C007 S1 116.7(2) . . ?
N003 C008 C006 113.5(2) . . ?
N003 C008 H008 107.3 . . ?
N003 C008 C00B 108.3(2) . . ?
C006 C008 H008 107.3 . . ?
C006 C008 C00B 112.8(2) . . ?
C00B C008 H008 107.3 . . ?
C007 C009 H009 120.3 . . ?
C00E C009 C007 119.4(3) . . ?
C00E C009 H009 120.3 . . ?
N004 C00A N003 178.6(3) . . ?
C008 C00B H00A 109.3 . . ?
C008 C00B H00B 109.3 . . ?
C008 C00B S1 111.64(18) . . ?
H00A C00B H00B 108.0 . . ?
S1 C00B H00A 109.3 . . ?
S1 C00B H00B 109.3 . . ?
C00E C00C H00C 120.5 . . ?
C00E C00C C00G 119.0(3) . . ?
C00G C00C H00C 120.5 . . ?
C006 C00D H00D 119.7 . . ?
C00H C00D C006 120.6(3) . . ?
C00H C00D H00D 119.7 . . ?
C009 C00E Br01 118.9(2) . . ?
C00C C00E Br01 119.6(2) . . ?
C00C C00E C009 121.5(3) . . ?
C006 C00F H00F 120.0 . . ?
C00J C00F C006 119.9(3) . . ?
C00J C00F H00F 120.0 . . ?
C005 C00G H00G 119.5 . . ?
C00C C00G C005 121.1(3) . . ?
C00C C00G H00G 119.5 . . ?
C00D C00H H00H 119.9 . . ?
C00I C00H C00D 120.1(3) . . ?
C00I C00H H00H 119.9 . . ?
C00H C00I H00I 120.1 . . ?
C00H C00I C00J 119.8(3) . . ?
C00J C00I H00I 120.1 . . ?
C00F C00J H00J 119.8 . . ?
C00I C00J C00F 120.5(3) . . ?
C00I C00J H00J 119.8 . . ?
C007 S1 C00B 98.83(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
