# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_cu_tc_673_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2221710'
loop_
_audit_author_name
_audit_author_address
'Yaseen Hussain '
;Indian Institute of Technology Jammu
India
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 Br O3 S'
_chemical_formula_weight         401.26

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'
O O 0.0492 0.0322 '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'

_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                   7.6268(5)
_cell_length_b                   9.3115(7)
_cell_length_c                   24.2573(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1722.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.504
_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      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15973
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.644
_diffrn_reflns_theta_max         66.504
_diffrn_reflns_theta_full        66.504
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3008
_reflns_number_gt                2940
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.983

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0293P)²+0.8608P] 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 1200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.139(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.31382(5) 0.96155(4) 0.39466(2) 0.03459(14) Uani 1 1 d . . . . .
S1 S 1.04108(10) 0.61126(8) 0.40871(3) 0.01925(18) Uani 1 1 d . . . . .
O1 O 1.0722(3) 0.3608(3) 0.32816(9) 0.0221(5) Uani 1 1 d . . . . .
O2 O 1.0709(4) 0.1393(3) 0.51176(10) 0.0334(6) Uani 1 1 d . . . . .
O3 O 1.1321(3) 0.4770(3) 0.24883(9) 0.0297(6) Uani 1 1 d . . . . .
C1 C 0.8379(4) 0.7052(3) 0.40569(13) 0.0187(6) Uani 1 1 d . . . . .
C2 C 0.7126(5) 0.6926(4) 0.44727(13) 0.0216(7) Uani 1 1 d . . . . .
H2 H 0.734672 0.632592 0.478175 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5560(5) 0.7672(4) 0.44363(14) 0.0234(7) Uani 1 1 d . . . . .
H3 H 0.468999 0.757079 0.471378 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5282(4) 0.8569(3) 0.39881(14) 0.0233(7) Uani 1 1 d . . . . .
C5 C 0.6502(5) 0.8710(4) 0.35695(13) 0.0228(7) Uani 1 1 d . . . . .
H5 H 0.627538 0.931587 0.326267 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8061(5) 0.7950(3) 0.36055(13) 0.0197(6) Uani 1 1 d . . . . .
H6 H 0.891556 0.803992 0.332282 0.024 Uiso 1 1 calc R U . . .
C7 C 0.9667(4) 0.4278(3) 0.42037(12) 0.0165(6) Uani 1 1 d . . . . .
H7 H 0.856318 0.433072 0.442506 0.020 Uiso 1 1 calc R U . . .
C8 C 0.9235(4) 0.3476(4) 0.36643(13) 0.0192(7) Uani 1 1 d . . . . .
C9 C 0.8949(5) 0.1898(4) 0.37709(15) 0.0239(7) Uani 1 1 d . . . . .
H9 H 0.841367 0.133828 0.348999 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9408(4) 0.1247(4) 0.42396(14) 0.0240(7) Uani 1 1 d . . . . .
H10 H 0.908505 0.027065 0.429159 0.029 Uiso 1 1 calc R U . . .
C11 C 1.0394(5) 0.1977(4) 0.46782(14) 0.0245(7) Uani 1 1 d . . . . .
C12 C 1.1026(5) 0.3477(4) 0.45506(14) 0.0230(7) Uani 1 1 d . . . . .
H12A H 1.214987 0.342694 0.434708 0.028 Uiso 1 1 calc R U . . .
H12B H 1.123303 0.400510 0.489880 0.028 Uiso 1 1 calc R U . . .
C13 C 1.0258(4) 0.4445(4) 0.28346(12) 0.0209(7) Uani 1 1 d . . . . .
C14 C 0.8382(4) 0.4785(4) 0.28799(13) 0.0203(7) Uani 1 1 d . . . . .
C15 C 0.7749(4) 0.4184(3) 0.33575(13) 0.0190(7) Uani 1 1 d . . . . .
C16 C 0.7337(4) 0.5613(4) 0.25324(14) 0.0252(7) Uani 1 1 d . . . . .
H16 H 0.779564 0.603807 0.220688 0.030 Uiso 1 1 calc R U . . .
C17 C 0.5597(5) 0.5788(4) 0.26835(14) 0.0275(8) Uani 1 1 d . . . . .
H17 H 0.484399 0.634683 0.245720 0.033 Uiso 1 1 calc R U . . .
C18 C 0.4932(4) 0.5159(4) 0.31606(15) 0.0275(8) Uani 1 1 d . . . . .
H18 H 0.372939 0.528481 0.325018 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6000(4) 0.4347(4) 0.35107(14) 0.0231(7) Uani 1 1 d . . . . .
H19 H 0.555246 0.392484 0.383831 0.028 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 C4 1.906(3) . ?
S1 C1 1.781(3) . ?
S1 C7 1.822(3) . ?
O1 C13 1.381(4) . ?
O1 C8 1.471(4) . ?
O2 C11 1.221(4) . ?
O3 C13 1.206(4) . ?
C1 C2 1.395(5) . ?
C1 C6 1.399(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(5) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.529(4) . ?
C7 C8 1.542(4) . ?
C7 H7 1.0000 . ?
C8 C15 1.507(4) . ?
C8 C9 1.508(5) . ?
C9 C10 1.336(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.470(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.510(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.469(5) . ?
C14 C15 1.374(5) . ?
C14 C16 1.393(5) . ?
C15 C19 1.393(5) . ?
C16 C17 1.386(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C1 S1 C7 101.31(14) . . ?
C13 O1 C8 110.2(2) . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 S1 121.7(2) . . ?
C6 C1 S1 118.5(2) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 Br1 119.3(2) . . ?
C3 C4 Br1 118.7(3) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 112.1(3) . . ?
C12 C7 S1 109.4(2) . . ?
C8 C7 S1 112.9(2) . . ?
C12 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
S1 C7 H7 107.4 . . ?
O1 C8 C15 103.4(3) . . ?
O1 C8 C9 107.5(3) . . ?
C15 C8 C9 113.7(3) . . ?
O1 C8 C7 109.3(2) . . ?
C15 C8 C7 111.6(3) . . ?
C9 C8 C7 110.9(3) . . ?
C10 C9 C8 123.4(3) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C9 C10 C11 122.7(3) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
O2 C11 C10 121.8(3) . . ?
O2 C11 C12 121.9(3) . . ?
C10 C11 C12 116.3(3) . . ?
C11 C12 C7 110.3(3) . . ?
C11 C12 H12A 109.6 . . ?
C7 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C7 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O3 C13 O1 121.1(3) . . ?
O3 C13 C14 130.7(3) . . ?
O1 C13 C14 108.2(3) . . ?
C15 C14 C16 122.3(3) . . ?
C15 C14 C13 108.5(3) . . ?
C16 C14 C13 129.1(3) . . ?
C14 C15 C19 121.1(3) . . ?
C14 C15 C8 109.3(3) . . ?
C19 C15 C8 129.5(3) . . ?
C17 C16 C14 116.9(3) . . ?
C17 C16 H16 121.5 . . ?
C14 C16 H16 121.5 . . ?
C16 C17 C18 121.3(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C15 C19 C18 117.0(3) . . ?
C15 C19 H19 121.5 . . ?
C18 C19 H19 121.5 . . ?

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
C7 S1 C1 C2 52.5(3) . . . . ?
C7 S1 C1 C6 -128.3(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
S1 C1 C2 C3 180.0(3) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C2 C3 C4 Br1 -179.1(3) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
Br1 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
S1 C1 C6 C5 -179.4(2) . . . . ?
C1 S1 C7 C12 -148.3(2) . . . . ?
C1 S1 C7 C8 86.2(2) . . . . ?
C13 O1 C8 C15 6.8(3) . . . . ?
C13 O1 C8 C9 127.4(3) . . . . ?
C13 O1 C8 C7 -112.1(3) . . . . ?
C12 C7 C8 O1 -72.8(3) . . . . ?
S1 C7 C8 O1 51.2(3) . . . . ?
C12 C7 C8 C15 173.5(3) . . . . ?
S1 C7 C8 C15 -62.5(3) . . . . ?
C12 C7 C8 C9 45.6(4) . . . . ?
S1 C7 C8 C9 169.6(2) . . . . ?
O1 C8 C9 C10 105.1(4) . . . . ?
C15 C8 C9 C10 -141.1(3) . . . . ?
C7 C8 C9 C10 -14.4(5) . . . . ?
C8 C9 C10 C11 -6.0(5) . . . . ?
C9 C10 C11 O2 175.4(3) . . . . ?
C9 C10 C11 C12 -5.8(5) . . . . ?
O2 C11 C12 C7 -144.5(3) . . . . ?
C10 C11 C12 C7 36.8(4) . . . . ?
C8 C7 C12 C11 -57.0(4) . . . . ?
S1 C7 C12 C11 177.0(2) . . . . ?
C8 O1 C13 O3 175.0(3) . . . . ?
C8 O1 C13 C14 -5.4(3) . . . . ?
O3 C13 C14 C15 -179.0(3) . . . . ?
O1 C13 C14 C15 1.5(4) . . . . ?
O3 C13 C14 C16 -1.5(6) . . . . ?
O1 C13 C14 C16 178.9(3) . . . . ?
C16 C14 C15 C19 1.7(5) . . . . ?
C13 C14 C15 C19 179.3(3) . . . . ?
C16 C14 C15 C8 -174.8(3) . . . . ?
C13 C14 C15 C8 2.9(4) . . . . ?
O1 C8 C15 C14 -5.9(3) . . . . ?
C9 C8 C15 C14 -122.1(3) . . . . ?
C7 C8 C15 C14 111.5(3) . . . . ?
O1 C8 C15 C19 178.1(3) . . . . ?
C9 C8 C15 C19 61.8(5) . . . . ?
C7 C8 C15 C19 -64.6(4) . . . . ?
C15 C14 C16 C17 -1.2(5) . . . . ?
C13 C14 C16 C17 -178.4(3) . . . . ?
C14 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 C19 1.1(6) . . . . ?
C14 C15 C19 C18 -0.7(5) . . . . ?
C8 C15 C19 C18 174.9(3) . . . . ?
C17 C18 C19 C15 -0.6(5) . . . . ?

_refine_diff_density_max         0.614
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.057

