# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_surjya_NTs_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hp74l
_database_code_depnum_ccdc_archive 'CCDC 2314309'
loop_
_audit_author_name
_audit_author_address
'Babula Das'
;IIT Guwahati
India
;
_audit_update_record             
;
2023-12-14 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br Cl2 N O2 S'
_chemical_formula_weight         463.20

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'
Cl Cl 0.1484 0.1585 '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'

_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                   11.812(2)
_cell_length_b                   15.310(3)
_cell_length_c                   11.343(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.195(5)
_cell_angle_gamma                90
_cell_volume                     1899.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   0.4346
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.567
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62323
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         28.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4681
_reflns_number_gt                3813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1146P)²+4.8817P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4681
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.2070
_refine_ls_wR_factor_gt          0.1888
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_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 -0.10224(5) 0.80364(4) 0.17899(5) 0.0565(2) Uani 1 1 d . . . . .
Cl1 Cl 0.13476(11) 0.82213(7) 0.40426(12) 0.0437(3) Uani 1 1 d . . . . .
Cl2 Cl 0.30805(18) 0.42564(11) -0.07157(14) 0.0706(5) Uani 1 1 d . . . . .
S1 S 0.25048(8) 0.51181(6) 0.52229(9) 0.0290(2) Uani 1 1 d . . . . .
O1 O 0.1877(3) 0.4718(2) 0.5942(3) 0.0416(7) Uani 1 1 d . . . . .
O2 O 0.3056(3) 0.45782(19) 0.4560(3) 0.0385(7) Uani 1 1 d . . . . .
N1 N 0.1483(3) 0.5757(2) 0.4150(3) 0.0261(6) Uani 1 1 d . . . . .
C1 C 0.3635(3) 0.5829(3) 0.6234(4) 0.0298(7) Uani 1 1 d . . . . .
C2 C 0.3525(4) 0.6165(3) 0.7321(4) 0.0353(8) Uani 1 1 d . . . . .
H2 H 0.288337 0.599120 0.755325 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4381(4) 0.6761(3) 0.8057(4) 0.0415(10) Uani 1 1 d . . . . .
H3 H 0.430298 0.699392 0.877950 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5360(4) 0.7020(3) 0.7732(5) 0.0404(10) Uani 1 1 d . . . . .
C5 C 0.5459(4) 0.6661(3) 0.6653(5) 0.0420(10) Uani 1 1 d . . . . .
H5 H 0.610664 0.682751 0.642515 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4616(4) 0.6062(3) 0.5907(4) 0.0360(8) Uani 1 1 d . . . . .
H6 H 0.470407 0.581822 0.519611 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6295(5) 0.7672(4) 0.8523(6) 0.0601(15) Uani 1 1 d . . . . .
H7A H 0.707003 0.755026 0.846631 0.090 Uiso 1 1 calc R U . . .
H7B H 0.637353 0.763109 0.939530 0.090 Uiso 1 1 calc R U . . .
H7C H 0.603730 0.825135 0.821228 0.090 Uiso 1 1 calc R U . . .
C8 C 0.1946(3) 0.6249(2) 0.3282(3) 0.0279(7) Uani 1 1 d . . . . .
H8 H 0.264683 0.660927 0.378926 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0922(4) 0.6840(3) 0.2384(4) 0.0328(8) Uani 1 1 d . . . . .
H9A H 0.126852 0.721607 0.191884 0.039 Uiso 1 1 calc R U . . .
H9B H 0.031215 0.647406 0.176822 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0296(4) 0.7404(3) 0.3046(4) 0.0319(8) Uani 1 1 d . . . . .
C11 C -0.0193(4) 0.6837(3) 0.3827(4) 0.0360(9) Uani 1 1 d . . . . .
H11A H -0.081590 0.644979 0.326916 0.043 Uiso 1 1 calc R U . . .
H11B H -0.056830 0.720052 0.427890 0.043 Uiso 1 1 calc R U . . .
C12 C 0.0818(4) 0.6302(3) 0.4771(4) 0.0354(8) Uani 1 1 d . . . . .
H12A H 0.139399 0.669118 0.538065 0.042 Uiso 1 1 calc R U . . .
H12B H 0.047209 0.592368 0.523499 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2306(3) 0.5666(2) 0.2394(4) 0.0297(7) Uani 1 1 d . . . . .
C14 C 0.1541(4) 0.5004(3) 0.1696(4) 0.0367(8) Uani 1 1 d . . . . .
H14 H 0.085050 0.485850 0.186002 0.044 Uiso 1 1 calc R U . . .
C15 C 0.1786(5) 0.4559(3) 0.0766(4) 0.0438(10) Uani 1 1 d . . . . .
H15 H 0.126907 0.411587 0.030442 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2820(5) 0.4782(3) 0.0527(4) 0.0433(10) Uani 1 1 d . . . . .
C17 C 0.3606(5) 0.5416(3) 0.1218(5) 0.0455(10) Uani 1 1 d . . . . .
H17 H 0.430533 0.554926 0.106278 0.055 Uiso 1 1 calc R U . . .
C18 C 0.3346(4) 0.5858(3) 0.2156(4) 0.0388(9) Uani 1 1 d . . . . .
H18 H 0.387776 0.628879 0.263154 0.047 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 C10 1.928(4) . ?
Cl1 C10 1.824(4) . ?
Cl2 C16 1.748(5) . ?
S1 O2 1.429(3) . ?
S1 O1 1.430(3) . ?
S1 N1 1.669(3) . ?
S1 C1 1.767(4) . ?
N1 C12 1.493(5) . ?
N1 C8 1.498(5) . ?
C1 C2 1.387(6) . ?
C1 C6 1.390(6) . ?
C2 C3 1.384(6) . ?
C3 C4 1.397(7) . ?
C4 C5 1.386(7) . ?
C4 C7 1.509(6) . ?
C5 C6 1.383(6) . ?
C8 C13 1.522(5) . ?
C8 C9 1.546(5) . ?
C9 C10 1.508(5) . ?
C10 C11 1.503(6) . ?
C11 C12 1.509(5) . ?
C13 C18 1.385(6) . ?
C13 C14 1.389(6) . ?
C14 C15 1.375(6) . ?
C15 C16 1.390(7) . ?
C16 C17 1.367(7) . ?
C17 C18 1.390(6) . ?

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 119.3(2) . . ?
O2 S1 N1 107.64(17) . . ?
O1 S1 N1 106.19(18) . . ?
O2 S1 C1 108.35(19) . . ?
O1 S1 C1 108.72(19) . . ?
N1 S1 C1 105.86(17) . . ?
C12 N1 C8 114.7(3) . . ?
C12 N1 S1 110.4(2) . . ?
C8 N1 S1 115.5(2) . . ?
C2 C1 C6 120.6(4) . . ?
C2 C1 S1 120.2(3) . . ?
C6 C1 S1 119.2(3) . . ?
C3 C2 C1 119.2(4) . . ?
C2 C3 C4 121.1(4) . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 C7 120.0(5) . . ?
C3 C4 C7 121.6(5) . . ?
C6 C5 C4 121.3(4) . . ?
C5 C6 C1 119.3(4) . . ?
N1 C8 C13 113.7(3) . . ?
N1 C8 C9 109.7(3) . . ?
C13 C8 C9 104.6(3) . . ?
C10 C9 C8 114.6(3) . . ?
C11 C10 C9 109.5(3) . . ?
C11 C10 Cl1 110.8(3) . . ?
C9 C10 Cl1 110.7(3) . . ?
C11 C10 Br1 110.1(3) . . ?
C9 C10 Br1 109.3(3) . . ?
Cl1 C10 Br1 106.5(2) . . ?
C10 C11 C12 110.8(3) . . ?
N1 C12 C11 112.6(3) . . ?
C18 C13 C14 118.5(4) . . ?
C18 C13 C8 119.6(3) . . ?
C14 C13 C8 121.5(4) . . ?
C15 C14 C13 121.3(4) . . ?
C14 C15 C16 118.9(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 Cl2 120.1(4) . . ?
C15 C16 Cl2 118.6(4) . . ?
C16 C17 C18 119.1(4) . . ?
C13 C18 C17 121.0(4) . . ?

_refine_diff_density_max         1.287
_refine_diff_density_min         -1.557
_refine_diff_density_rms         0.123



