# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_exp_3880
_database_code_depnum_ccdc_archive 'CCDC 2167617'
loop_
_audit_author_name
_audit_author_address
'Xiaobao Zeng'
;Nantong University
China
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-08 downloaded from the CCDC.
;
_audit_creation_date             2022-04-20
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 Br N2 O S'
_chemical_formula_sum            'C17 H11 Br N2 O S'
_chemical_formula_weight         371.25
_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/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                   12.8390(12)
_cell_length_b                   9.1349(11)
_cell_length_c                   13.4055(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.269(11)
_cell_angle_gamma                90
_cell_volume                     1551.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    249.97(10)
_cell_measurement_theta_max      25.0820
_cell_measurement_theta_min      2.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.786
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05509
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.398
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      249.97(10)
_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     44.00  98.00   1.00    5.00    --   12.05-178.00-180.00   54
  2  ω     35.00  86.00   1.00    5.00    --   12.05-178.00 -90.00   51
  3  ω    -28.00  63.00   1.00    5.00    --   12.05  19.00   0.00   91
;
_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      0.0127090000
_diffrn_orient_matrix_UB_12      -0.0424528000
_diffrn_orient_matrix_UB_13      -0.0406478000
_diffrn_orient_matrix_UB_21      0.0275405000
_diffrn_orient_matrix_UB_22      -0.0504832000
_diffrn_orient_matrix_UB_23      0.0348813000
_diffrn_orient_matrix_UB_31      -0.0470678000
_diffrn_orient_matrix_UB_32      -0.0410579000
_diffrn_orient_matrix_UB_33      -0.0008943000
_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                1853
_reflns_number_total             2726
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      0.991
_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1260
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
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)
;
_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 1.01398(4) 0.58833(6) 0.23082(5) 0.0740(3) Uani 1 1 d . . . . .
S1 S 0.64972(11) 0.78101(14) 0.53851(9) 0.0564(4) Uani 1 1 d . . . . .
O1 O 0.6114(2) 0.4074(3) 0.1485(2) 0.0508(8) Uani 1 1 d . . . . .
N2 N 0.6809(4) 1.0826(5) 0.5089(4) 0.0738(14) Uani 1 1 d . . . . .
N1 N 0.6734(2) 0.5556(4) 0.2842(3) 0.0363(8) Uani 1 1 d . . . . .
C1 C 0.5186(3) 0.5946(4) 0.3457(3) 0.0348(10) Uani 1 1 d . . . . .
C2 C 0.4368(3) 0.6381(5) 0.3948(3) 0.0468(11) Uani 1 1 d . . . . .
H2 H 0.449416 0.696684 0.452228 0.056 Uiso 1 1 calc R U . . .
C3 C 0.3346(4) 0.5915(5) 0.3554(4) 0.0529(13) Uani 1 1 d . . . . .
H3 H 0.278591 0.620182 0.387113 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3153(3) 0.5045(6) 0.2714(4) 0.0558(13) Uani 1 1 d . . . . .
H4 H 0.246574 0.475069 0.247027 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3963(3) 0.4600(5) 0.2223(3) 0.0474(12) Uani 1 1 d . . . . .
H5 H 0.383199 0.400616 0.165360 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4976(3) 0.5061(5) 0.2601(3) 0.0372(10) Uani 1 1 d . . . . .
C7 C 0.5964(3) 0.4792(5) 0.2210(3) 0.0371(10) Uani 1 1 d . . . . .
C8 C 0.6335(3) 0.6286(4) 0.3627(3) 0.0337(10) Uani 1 1 d . . . . .
C9 C 0.6946(3) 0.7065(5) 0.4325(3) 0.0432(11) Uani 1 1 d . . . . .
H9 H 0.764405 0.722305 0.424925 0.052 Uiso 1 1 calc R U . . .
C10 C 0.6677(4) 0.9599(6) 0.5181(3) 0.0482(12) Uani 1 1 d . . . . .
C11 C 0.7817(3) 0.5638(4) 0.2656(3) 0.0365(10) Uani 1 1 d . . . . .
H11A H 0.807321 0.662900 0.279008 0.044 Uiso 1 1 calc R U . . .
H11B H 0.782577 0.543548 0.194684 0.044 Uiso 1 1 calc R U . . .
C12 C 0.8566(3) 0.4588(4) 0.3288(3) 0.0314(9) Uani 1 1 d . . . . .
C13 C 0.9627(3) 0.4554(5) 0.3214(3) 0.0410(11) Uani 1 1 d . . . . .
C14 C 1.0338(4) 0.3622(6) 0.3757(4) 0.0591(14) Uani 1 1 d . . . . .
H14 H 1.104517 0.364294 0.368228 0.071 Uiso 1 1 calc R U . . .
C15 C 0.9986(4) 0.2650(6) 0.4417(4) 0.0646(15) Uani 1 1 d . . . . .
H15 H 1.045662 0.200883 0.479394 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8934(4) 0.2636(5) 0.4514(4) 0.0614(14) Uani 1 1 d . . . . .
H16 H 0.869334 0.198372 0.495851 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8235(4) 0.3590(5) 0.3953(3) 0.0458(11) Uani 1 1 d . . . . .
H17 H 0.752634 0.356135 0.402229 0.055 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 1.908(4) . ?
S1 C9 1.754(4) . ?
S1 C10 1.679(6) . ?
O1 C7 1.214(5) . ?
N2 C10 1.143(5) . ?
N1 C7 1.383(5) . ?
N1 C8 1.409(5) . ?
N1 C11 1.454(5) . ?
C1 C2 1.384(5) . ?
C1 C6 1.394(6) . ?
C1 C8 1.489(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 C7 1.470(5) . ?
C8 C9 1.327(5) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.517(5) . ?
C12 C13 1.382(5) . ?
C12 C17 1.389(6) . ?
C13 C14 1.369(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(6) . ?
C17 H17 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 100.0(2) . . ?
C7 N1 C8 112.8(3) . . ?
C7 N1 C11 121.9(3) . . ?
C8 N1 C11 125.2(3) . . ?
C2 C1 C6 119.8(4) . . ?
C2 C1 C8 132.6(4) . . ?
C6 C1 C8 107.6(3) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.1(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(4) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 109.1(3) . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 C7 129.3(4) . . ?
O1 C7 N1 125.1(4) . . ?
O1 C7 C6 129.3(4) . . ?
N1 C7 C6 105.7(3) . . ?
N1 C8 C1 104.9(3) . . ?
C9 C8 N1 122.4(4) . . ?
C9 C8 C1 132.7(4) . . ?
S1 C9 H9 118.4 . . ?
C8 C9 S1 123.1(3) . . ?
C8 C9 H9 118.4 . . ?
N2 C10 S1 176.8(5) . . ?
N1 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
N1 C11 C12 114.2(3) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 C17 116.0(4) . . ?
C17 C12 C11 122.8(4) . . ?
C12 C13 Br1 118.5(3) . . ?
C14 C13 Br1 117.8(3) . . ?
C14 C13 C12 123.8(4) . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(4) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.6(4) . . ?
C16 C17 H17 119.2 . . ?

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 180.0(4) . . . . ?
N1 C8 C9 S1 -172.7(3) . . . . ?
N1 C11 C12 C13 -178.7(4) . . . . ?
N1 C11 C12 C17 2.8(6) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C1 C6 C7 O1 179.6(5) . . . . ?
C1 C6 C7 N1 -1.1(5) . . . . ?
C1 C8 C9 S1 6.7(7) . . . . ?
C2 C1 C6 C5 0.0(7) . . . . ?
C2 C1 C6 C7 178.4(4) . . . . ?
C2 C1 C8 N1 -177.4(5) . . . . ?
C2 C1 C8 C9 3.1(8) . . . . ?
C2 C3 C4 C5 -0.1(8) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C4 C5 C6 C7 -177.7(5) . . . . ?
C5 C6 C7 O1 -2.1(8) . . . . ?
C5 C6 C7 N1 177.2(4) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C6 C1 C8 N1 -0.2(4) . . . . ?
C6 C1 C8 C9 -179.7(5) . . . . ?
C7 N1 C8 C1 -0.5(5) . . . . ?
C7 N1 C8 C9 179.0(4) . . . . ?
C7 N1 C11 C12 -99.9(5) . . . . ?
C8 N1 C7 O1 -179.7(4) . . . . ?
C8 N1 C7 C6 1.0(5) . . . . ?
C8 N1 C11 C12 83.8(5) . . . . ?
C8 C1 C2 C3 176.5(4) . . . . ?
C8 C1 C6 C5 -177.6(4) . . . . ?
C8 C1 C6 C7 0.8(5) . . . . ?
C10 S1 C9 C8 -118.4(4) . . . . ?
C11 N1 C7 O1 3.6(7) . . . . ?
C11 N1 C7 C6 -175.7(4) . . . . ?
C11 N1 C8 C1 176.1(4) . . . . ?
C11 N1 C8 C9 -4.4(6) . . . . ?
C11 C12 C13 Br1 1.0(5) . . . . ?
C11 C12 C13 C14 -179.3(4) . . . . ?
C11 C12 C17 C16 179.4(4) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C13 C12 C17 C16 0.9(7) . . . . ?
C13 C14 C15 C16 0.1(8) . . . . ?
C14 C15 C16 C17 0.0(8) . . . . ?
C15 C16 C17 C12 -0.6(8) . . . . ?
C17 C12 C13 Br1 179.5(3) . . . . ?
C17 C12 C13 C14 -0.8(7) . . . . ?

_olex2_date_sample_data_collection 2022-04-20
_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 6.399
_oxdiff_exptl_absorpt_empirical_full_min 0.420
