# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_KM0401_0m
_database_code_depnum_ccdc_archive 'CCDC 1572813'
loop_
_audit_author_name
_audit_author_address
'Santa Mondal'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2022-09-07 deposited with the CCDC.	2022-11-28 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            'C16 H9 Br O S3'
_chemical_formula_weight         393.32

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5072(2)
_cell_length_b                   12.8308(4)
_cell_length_c                   21.2270(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1499.94(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5170
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      20.20

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   0.420
_exptl_transmission_factor_max   0.500
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    3.152
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14731
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.855
_diffrn_reflns_theta_max         25.042
_diffrn_reflns_theta_full        25.042
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2580
_reflns_number_gt                2162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.933

_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)+(0.0100P)²+3.3656P] 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_abs_structure_details 
;
 Flack x determined using 742 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.457(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_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 0.36564(16) 1.38824(6) 0.19897(4) 0.0561(2) Uani 1 1 d . . . . .
S2 S 0.5775(4) 0.76032(14) 0.06411(9) 0.0482(5) Uani 1 1 d . . . . .
S3 S 0.8264(4) 1.04643(15) -0.03311(9) 0.0548(6) Uani 1 1 d . . . . .
S4 S 0.5454(4) 0.94053(16) -0.02073(10) 0.0579(6) Uani 1 1 d . . . . .
C2 C 0.5738(13) 1.1066(6) 0.1217(3) 0.0433(18) Uani 1 1 d . . . . .
H2 H 0.515919 1.038507 0.122637 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8625(16) 1.2314(5) 0.0874(3) 0.0471(19) Uani 1 1 d . . . . .
H4 H 1.000262 1.248462 0.064266 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7428(14) 1.3088(5) 0.1204(4) 0.045(2) Uani 1 1 d . . . . .
H5 H 0.801234 1.376787 0.120463 0.054 Uiso 1 1 calc R U . . .
C3 C 0.7823(13) 1.1286(5) 0.0879(3) 0.0378(18) Uani 1 1 d . . . . .
C1 C 0.4496(15) 1.1832(5) 0.1539(3) 0.0444(19) Uani 1 1 d . . . . .
H1 H 0.308619 1.166965 0.175948 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8626(15) 0.5940(5) 0.2035(3) 0.0495(18) Uani 1 1 d . . . . .
H8 H 0.832318 0.529174 0.221420 0.059 Uiso 1 1 calc R U . . .
C6 C 1.0942(13) 0.7507(5) 0.1995(3) 0.0438(17) Uani 1 1 d . . . . .
H6 H 1.220996 0.791216 0.214940 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9491(13) 0.7903(5) 0.1511(3) 0.0359(17) Uani 1 1 d . . . . .
C7 C 1.0550(16) 0.6539(6) 0.2247(3) 0.052(2) Uani 1 1 d . . . . .
H7 H 1.157315 0.628536 0.255953 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7166(14) 0.6304(5) 0.1559(3) 0.045(2) Uani 1 1 d . . . . .
H9 H 0.587304 0.590070 0.141723 0.055 Uiso 1 1 calc R U . . .
C10 C 0.7611(13) 0.7279(5) 0.1285(3) 0.0385(18) Uani 1 1 d . . . . .
O1 O 1.1433(11) 0.9543(4) 0.1555(2) 0.0609(15) Uani 1 1 d . . . . .
C12 C 0.9976(13) 0.8978(6) 0.1282(3) 0.0399(17) Uani 1 1 d . . . . .
C13 C 0.8670(14) 0.9346(5) 0.0733(3) 0.0376(16) Uani 1 1 d . . . . .
C14 C 0.6904(13) 0.8810(6) 0.0437(3) 0.0412(18) Uani 1 1 d . . . . .
C15 C 0.9137(13) 1.0459(5) 0.0504(3) 0.0407(18) Uani 1 1 d . . . . .
H15 H 1.088480 1.059590 0.053099 0.049 Uiso 1 1 calc R U . . .
C17 C 0.5357(14) 1.2834(5) 0.1532(3) 0.0418(19) 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
Br1 C17 1.905(7) . ?
S2 C14 1.724(7) . ?
S2 C10 1.751(7) . ?
S3 C15 1.836(7) . ?
S3 S4 2.076(3) . ?
S4 C14 1.759(7) . ?
C2 C1 1.380(10) . ?
C2 C3 1.382(9) . ?
C4 C5 1.383(10) . ?
C4 C3 1.391(9) . ?
C5 C17 1.375(10) . ?
C3 C15 1.511(9) . ?
C1 C17 1.370(9) . ?
C8 C9 1.373(10) . ?
C8 C7 1.384(11) . ?
C6 C7 1.370(9) . ?
C6 C11 1.396(9) . ?
C11 C10 1.394(9) . ?
C11 C12 1.487(9) . ?
C9 C10 1.401(9) . ?
O1 C12 1.228(8) . ?
C12 C13 1.448(9) . ?
C13 C14 1.346(9) . ?
C13 C15 1.530(9) . ?

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
C14 S2 C10 101.6(3) . . ?
C15 S3 S4 94.1(2) . . ?
C14 S4 S3 92.5(3) . . ?
C1 C2 C3 121.6(7) . . ?
C5 C4 C3 121.7(7) . . ?
C17 C5 C4 118.8(7) . . ?
C2 C3 C4 117.5(7) . . ?
C2 C3 C15 121.9(6) . . ?
C4 C3 C15 120.6(7) . . ?
C17 C1 C2 119.5(7) . . ?
C9 C8 C7 119.9(7) . . ?
C7 C6 C11 121.8(7) . . ?
C10 C11 C6 118.0(6) . . ?
C10 C11 C12 123.6(6) . . ?
C6 C11 C12 118.4(6) . . ?
C6 C7 C8 119.8(7) . . ?
C8 C9 C10 120.4(7) . . ?
C11 C10 C9 120.0(7) . . ?
C11 C10 S2 124.2(5) . . ?
C9 C10 S2 115.8(6) . . ?
O1 C12 C13 120.8(7) . . ?
O1 C12 C11 120.7(6) . . ?
C13 C12 C11 118.5(6) . . ?
C14 C13 C12 124.5(6) . . ?
C14 C13 C15 116.8(6) . . ?
C12 C13 C15 118.4(6) . . ?
C13 C14 S2 127.1(5) . . ?
C13 C14 S4 118.0(6) . . ?
S2 C14 S4 114.9(4) . . ?
C3 C15 C13 114.0(5) . . ?
C3 C15 S3 112.4(5) . . ?
C13 C15 S3 105.4(5) . . ?
C1 C17 C5 120.9(7) . . ?
C1 C17 Br1 119.2(6) . . ?
C5 C17 Br1 119.9(5) . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051

