# Supplementary Information (SI) for ChemComm.
# 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_as_56
_database_code_depnum_ccdc_archive 'CCDC 2377196'
loop_
_audit_author_name
_audit_author_address
'ANITA SAHOO'
;IIT GUWAHATI
India
;
_audit_update_record             
;
2024-08-13 deposited with the CCDC.	2024-11-12 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            'C19 H19 Br N2 O2 S'
_chemical_formula_weight         419.33

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'

_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                   9.7614(11)
_cell_length_b                   25.463(3)
_cell_length_c                   7.4877(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.531(4)
_cell_angle_gamma                90
_cell_volume                     1793.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.01

_exptl_crystal_description       needle
_exptl_crystal_colour            colouress
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.424
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            34319
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3157
_reflns_number_gt                2767
_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)+(0.0341P)²+2.5161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 1.37756(4) 0.07102(2) 0.35434(6) 0.05455(16) Uani 1 1 d . . . . .
S1 S 0.62012(8) 0.18411(3) 1.06929(11) 0.0369(2) Uani 1 1 d . . . . .
O2 O 0.6049(3) 0.13312(11) 1.1399(4) 0.0538(7) Uani 1 1 d . . . . .
O1 O 0.6847(3) 0.22519(12) 1.1932(4) 0.0591(7) Uani 1 1 d . . . . .
N1 N 0.7189(3) 0.17778(12) 0.9284(4) 0.0354(6) Uani 1 1 d . . . . .
N2 N 1.0528(3) 0.03355(10) 0.8080(4) 0.0380(6) Uani 1 1 d . . . . .
C19 C 1.0680(3) 0.05341(11) 0.6445(4) 0.0287(6) Uani 1 1 d . . . . .
C15 C 1.1981(3) 0.04938(11) 0.5940(4) 0.0304(6) Uani 1 1 d . . . . .
C11 C 0.9475(3) 0.07858(11) 0.5231(4) 0.0309(7) Uani 1 1 d . . . . .
C14 C 1.2040(3) 0.07150(12) 0.4235(4) 0.0346(7) Uani 1 1 d . . . . .
C10 C 0.8120(3) 0.08477(13) 0.5818(5) 0.0363(7) Uani 1 1 d . . . . .
H10A H 0.792317 0.052438 0.638861 0.044 Uiso 1 1 calc R U . . .
H10B H 0.733466 0.091327 0.473450 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4509(3) 0.20577(12) 0.9419(4) 0.0314(7) Uani 1 1 d . . . . .
C16 C 1.3119(3) 0.02312(13) 0.7199(5) 0.0398(8) Uani 1 1 d . . . . .
H16 H 1.399179 0.019820 0.693183 0.048 Uiso 1 1 calc R U . . .
C12 C 0.9595(3) 0.09791(13) 0.3582(4) 0.0365(7) Uani 1 1 d . . . . .
H12 H 0.881200 0.113727 0.277332 0.044 Uiso 1 1 calc R U . . .
C8 C 0.6940(3) 0.13484(13) 0.7934(5) 0.0361(7) Uani 1 1 d . . . . .
H8A H 0.610179 0.142115 0.692881 0.043 Uiso 1 1 calc R U . . .
H8B H 0.678688 0.102240 0.852306 0.043 Uiso 1 1 calc R U . . .
C13 C 1.0888(3) 0.09433(13) 0.3079(5) 0.0394(7) Uani 1 1 d . . . . .
H13 H 1.094714 0.107756 0.194739 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4246(3) 0.25843(13) 0.9141(5) 0.0391(8) Uani 1 1 d . . . . .
H4 H 0.495038 0.282857 0.965325 0.047 Uiso 1 1 calc R U . . .
C2 C 0.1867(3) 0.23944(14) 0.7311(5) 0.0409(8) Uani 1 1 d . . . . .
C6 C 0.3476(4) 0.16934(13) 0.8647(5) 0.0420(8) Uani 1 1 d . . . . .
H6 H 0.365682 0.133614 0.883323 0.050 Uiso 1 1 calc R U . . .
C9 C 0.8236(3) 0.13001(13) 0.7189(5) 0.0416(8) Uani 1 1 d . . . . .
H9A H 0.907169 0.124789 0.821838 0.050 Uiso 1 1 calc R U . . .
H9B H 0.836078 0.162602 0.658066 0.050 Uiso 1 1 calc R U . . .
C18 C 1.1618(4) 0.00928(14) 0.9177(5) 0.0460(8) Uani 1 1 d . . . . .
H18 H 1.151057 -0.004551 1.028112 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2161(3) 0.18674(14) 0.7586(5) 0.0446(8) Uani 1 1 d . . . . .
H7 H 0.146477 0.162269 0.705115 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2926(4) 0.27494(14) 0.8092(5) 0.0425(8) Uani 1 1 d . . . . .
H3 H 0.274876 0.310690 0.790929 0.051 Uiso 1 1 calc R U . . .
C17 C 1.2938(4) 0.00291(14) 0.8784(5) 0.0468(9) Uani 1 1 d . . . . .
H17 H 1.367401 -0.014966 0.960497 0.056 Uiso 1 1 calc R U . . .
C1 C 0.0425(4) 0.25827(18) 0.6182(6) 0.0595(11) Uani 1 1 d . . . . .
H1A H -0.004676 0.230479 0.538530 0.089 Uiso 1 1 calc R U . . .
H1B H 0.054382 0.287888 0.544372 0.089 Uiso 1 1 calc R U . . .
H1C H -0.013641 0.268412 0.699924 0.089 Uiso 1 1 calc R U . . .
H1 H 0.720(4) 0.2054(14) 0.881(5) 0.035(10) Uiso 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
Br1 C14 1.900(3) . ?
S1 O2 1.424(3) . ?
S1 O1 1.428(3) . ?
S1 N1 1.616(3) . ?
S1 C5 1.761(3) . ?
N1 C8 1.464(4) . ?
N1 H1 0.79(3) . ?
N2 C18 1.311(4) . ?
N2 C19 1.369(4) . ?
C19 C15 1.423(4) . ?
C19 C11 1.431(4) . ?
C15 C14 1.411(4) . ?
C15 C16 1.417(4) . ?
C11 C12 1.363(4) . ?
C11 C10 1.510(4) . ?
C14 C13 1.353(5) . ?
C10 C9 1.527(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C4 1.371(4) . ?
C5 C6 1.378(5) . ?
C16 C17 1.348(5) . ?
C16 H16 0.9300 . ?
C12 C13 1.413(4) . ?
C12 H12 0.9300 . ?
C8 C9 1.518(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13 0.9300 . ?
C4 C3 1.383(5) . ?
C4 H4 0.9300 . ?
C2 C7 1.376(5) . ?
C2 C3 1.380(5) . ?
C2 C1 1.513(5) . ?
C6 C7 1.389(5) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C18 C17 1.405(5) . ?
C18 H18 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 119.89(18) . . ?
O2 S1 N1 106.91(16) . . ?
O1 S1 N1 105.10(16) . . ?
O2 S1 C5 108.10(15) . . ?
O1 S1 C5 108.01(15) . . ?
N1 S1 C5 108.36(15) . . ?
C8 N1 S1 120.5(2) . . ?
C8 N1 H1 112(3) . . ?
S1 N1 H1 107(3) . . ?
C18 N2 C19 118.1(3) . . ?
N2 C19 C15 122.0(3) . . ?
N2 C19 C11 117.8(3) . . ?
C15 C19 C11 120.2(3) . . ?
C14 C15 C16 125.2(3) . . ?
C14 C15 C19 117.9(3) . . ?
C16 C15 C19 117.0(3) . . ?
C12 C11 C19 118.8(3) . . ?
C12 C11 C10 121.4(3) . . ?
C19 C11 C10 119.8(3) . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 Br1 118.5(2) . . ?
C15 C14 Br1 120.0(2) . . ?
C11 C10 C9 111.2(3) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 S1 119.9(2) . . ?
C6 C5 S1 119.4(2) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N1 C8 C9 108.3(3) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C7 C2 C3 118.2(3) . . ?
C7 C2 C1 121.2(3) . . ?
C3 C2 C1 120.6(3) . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C9 C10 112.9(3) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C18 C17 124.0(3) . . ?
N2 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C16 C17 C18 118.9(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
O2 S1 N1 C8 44.7(3) . . . . ?
O1 S1 N1 C8 173.1(3) . . . . ?
C5 S1 N1 C8 -71.6(3) . . . . ?
C18 N2 C19 C15 -1.5(4) . . . . ?
C18 N2 C19 C11 178.3(3) . . . . ?
N2 C19 C15 C14 -179.4(3) . . . . ?
C11 C19 C15 C14 0.9(4) . . . . ?
N2 C19 C15 C16 0.8(4) . . . . ?
C11 C19 C15 C16 -178.9(3) . . . . ?
N2 C19 C11 C12 -179.0(3) . . . . ?
C15 C19 C11 C12 0.8(4) . . . . ?
N2 C19 C11 C10 2.9(4) . . . . ?
C15 C19 C11 C10 -177.3(3) . . . . ?
C16 C15 C14 C13 177.6(3) . . . . ?
C19 C15 C14 C13 -2.2(4) . . . . ?
C16 C15 C14 Br1 -3.8(4) . . . . ?
C19 C15 C14 Br1 176.4(2) . . . . ?
C12 C11 C10 C9 -100.1(4) . . . . ?
C19 C11 C10 C9 77.9(4) . . . . ?
O2 S1 C5 C4 157.2(3) . . . . ?
O1 S1 C5 C4 26.1(3) . . . . ?
N1 S1 C5 C4 -87.3(3) . . . . ?
O2 S1 C5 C6 -25.4(3) . . . . ?
O1 S1 C5 C6 -156.6(3) . . . . ?
N1 S1 C5 C6 90.1(3) . . . . ?
C14 C15 C16 C17 -179.2(3) . . . . ?
C19 C15 C16 C17 0.6(5) . . . . ?
C19 C11 C12 C13 -1.2(5) . . . . ?
C10 C11 C12 C13 176.8(3) . . . . ?
S1 N1 C8 C9 -164.9(2) . . . . ?
C15 C14 C13 C12 1.8(5) . . . . ?
Br1 C14 C13 C12 -176.8(2) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
S1 C5 C4 C3 178.1(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
S1 C5 C6 C7 -177.6(3) . . . . ?
N1 C8 C9 C10 177.7(3) . . . . ?
C11 C10 C9 C8 -175.4(3) . . . . ?
C19 N2 C18 C17 0.7(5) . . . . ?
C3 C2 C7 C6 1.2(5) . . . . ?
C1 C2 C7 C6 -179.0(3) . . . . ?
C5 C6 C7 C2 -0.7(5) . . . . ?
C7 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C5 C4 C3 C2 -0.3(5) . . . . ?
C15 C16 C17 C18 -1.3(5) . . . . ?
N2 C18 C17 C16 0.6(6) . . . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.061



