# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_SHL09
_database_code_depnum_ccdc_archive 'CCDC 2255995'
loop_
_audit_author_name
_audit_author_address
'Aijaz Dar'
;University of Kashmir
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N4 O9 S'
_chemical_formula_sum            'C20 H16 N4 O9 S'
_chemical_formula_weight         488.43

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'
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      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                   10.7818(7)
_cell_length_b                   12.1565(11)
_cell_length_c                   15.1497(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1985.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2802
_cell_measurement_theta_min      1.532
_cell_measurement_theta_max      25.000

_exptl_crystal_description       blocks
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   0.322
_exptl_transmission_factor_max   0.342
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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 D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3988
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.891
_reflns_number_total             3125
_reflns_number_gt                2802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.570
_reflns_Friedel_fraction_max     0.757
_reflns_Friedel_fraction_full    0.757

_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-2018/1 (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)+(0.1061P)²] 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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1748
_refine_ls_wR_factor_gt          0.1657
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
S1 S 0.15106(12) 0.26753(13) 0.15456(9) 0.0155(4) Uani 1 1 d . . . . .
O7 O 0.3336(4) 0.2901(4) 0.6611(3) 0.0234(10) Uani 1 1 d . . . . .
O2 O 0.0499(4) 0.3244(4) 0.1988(3) 0.0183(10) Uani 1 1 d . . . . .
O3 O 0.1116(4) 0.2098(4) 0.0757(3) 0.0208(10) Uani 1 1 d . . . . .
O6 O 0.2813(5) 0.2491(4) 0.4879(3) 0.0246(11) Uani 1 1 d . . . . .
H6A H 0.309162 0.261436 0.537328 0.037 Uiso 1 1 calc R U . . .
O5 O 0.3376(5) 0.0772(4) 0.5216(3) 0.0276(11) Uani 1 1 d . . . . .
O1 O 0.2567(4) 0.3402(4) 0.1390(3) 0.0199(10) Uani 1 1 d . . . . .
O4 O 0.3250(5) -0.0754(4) 0.4008(3) 0.0291(11) Uani 1 1 d . . . . .
H4A H 0.325787 -0.053353 0.451972 0.044 Uiso 1 1 calc R U . . .
O9 O 0.4569(5) 0.7303(4) 0.1383(3) 0.0318(12) Uani 1 1 d . . . . .
O8 O 0.3975(5) 0.5630(5) 0.1125(3) 0.0350(13) Uani 1 1 d . . . . .
N1 N 0.3355(4) 0.4093(4) 0.9703(3) 0.0180(11) Uani 1 1 d . . . . .
H1N H 0.323835 0.415879 1.026191 0.022 Uiso 1 1 calc R U . . .
N2 N 0.4399(4) 0.4521(5) 0.6505(3) 0.0178(11) Uani 1 1 d . . . . .
H2N H 0.480470 0.502558 0.677822 0.021 Uiso 1 1 calc R U . . .
N4 N 0.4344(5) 0.6355(5) 0.1623(4) 0.0214(12) Uani 1 1 d . . . . .
N3 N 0.4334(5) 0.4515(4) 0.5599(3) 0.0183(12) Uani 1 1 d . . . . .
C21 C 0.3136(5) 0.3065(6) 0.8416(4) 0.0173(13) Uani 1 1 d . . . . .
H21 H 0.286884 0.243018 0.813079 0.021 Uiso 1 1 calc R U . . .
C20 C 0.2946(5) 0.3180(6) 0.9295(4) 0.0187(13) Uani 1 1 d . . . . .
H20 H 0.253778 0.263412 0.961250 0.022 Uiso 1 1 calc R U . . .
C16 C 0.3722(5) 0.3883(5) 0.7938(4) 0.0143(13) Uani 1 1 d . . . . .
C2 C 0.2242(5) 0.1939(5) 0.3168(4) 0.0151(12) Uani 1 1 d . . . . .
H2 H 0.210879 0.265850 0.335497 0.018 Uiso 1 1 calc R U . . .
C8 C 0.4505(5) 0.6065(5) 0.2551(4) 0.0174(13) Uani 1 1 d . . . . .
C13 C 0.4998(5) 0.6861(6) 0.3109(4) 0.0190(13) Uani 1 1 d . . . . .
H13 H 0.522278 0.755283 0.290071 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2669(5) 0.1151(5) 0.3766(4) 0.0158(13) Uani 1 1 d . . . . .
C6 C 0.2201(6) 0.0582(6) 0.2018(4) 0.0191(14) Uani 1 1 d . . . . .
H6 H 0.204477 0.039444 0.143315 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4805(5) 0.5522(6) 0.4285(4) 0.0166(13) Uani 1 1 d . . . . .
C7 C 0.2971(6) 0.1442(6) 0.4685(4) 0.0226(14) Uani 1 1 d . . . . .
C15 C 0.3816(5) 0.3721(5) 0.6952(4) 0.0166(13) Uani 1 1 d . . . . .
C9 C 0.4168(5) 0.5020(6) 0.2829(4) 0.0179(13) Uani 1 1 d . . . . .
H9 H 0.385046 0.450859 0.243230 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4314(6) 0.4757(5) 0.3708(4) 0.0195(14) Uani 1 1 d . . . . .
H10 H 0.408327 0.406495 0.391212 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5140(5) 0.6580(5) 0.3987(4) 0.0187(14) Uani 1 1 d . . . . .
H12 H 0.545707 0.709197 0.438378 0.022 Uiso 1 1 calc R U . . .
C17 C 0.4130(6) 0.4826(5) 0.8381(4) 0.0189(13) Uani 1 1 d . . . . .
H17 H 0.452460 0.538903 0.807489 0.023 Uiso 1 1 calc R U . . .
C1 C 0.2014(5) 0.1652(5) 0.2295(4) 0.0131(12) Uani 1 1 d . . . . .
C14 C 0.4893(6) 0.5317(6) 0.5237(4) 0.0199(14) Uani 1 1 d . . . . .
H14 H 0.536971 0.578587 0.558351 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3940(5) 0.4909(6) 0.9268(4) 0.0183(14) Uani 1 1 d . . . . .
H18 H 0.421310 0.552772 0.957217 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2844(5) 0.0061(5) 0.3470(4) 0.0194(14) Uani 1 1 d . . . . .
C5 C 0.2615(6) -0.0211(5) 0.2596(4) 0.0224(15) Uani 1 1 d . . . . .
H5 H 0.274185 -0.092782 0.240061 0.027 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
S1 O3 1.449(4) . ?
S1 O2 1.455(4) . ?
S1 O1 1.460(4) . ?
S1 C1 1.769(6) . ?
O7 C15 1.237(8) . ?
O6 C7 1.319(9) . ?
O6 H6A 0.8200 . ?
O5 C7 1.225(8) . ?
O4 C4 1.355(8) . ?
O4 H4A 0.8200 . ?
O9 N4 1.233(7) . ?
O8 N4 1.227(7) . ?
N1 C20 1.345(8) . ?
N1 C18 1.348(8) . ?
N1 H1N 0.8600 . ?
N2 C15 1.342(8) . ?
N2 N3 1.373(7) . ?
N2 H2N 0.8600 . ?
N4 C8 1.459(8) . ?
N3 C14 1.272(8) . ?
C21 C20 1.355(8) . ?
C21 C16 1.383(9) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C16 C17 1.400(9) . ?
C16 C15 1.510(8) . ?
C2 C1 1.390(8) . ?
C2 C3 1.397(9) . ?
C2 H2 0.9300 . ?
C8 C9 1.387(9) . ?
C8 C13 1.391(9) . ?
C13 C12 1.381(9) . ?
C13 H13 0.9300 . ?
C3 C4 1.411(9) . ?
C3 C7 1.473(9) . ?
C6 C5 1.377(9) . ?
C6 C1 1.382(9) . ?
C6 H6 0.9300 . ?
C11 C10 1.383(9) . ?
C11 C12 1.410(9) . ?
C11 C14 1.466(9) . ?
C9 C10 1.378(9) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C17 C18 1.362(8) . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C4 C5 1.387(9) . ?
C5 H5 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
O3 S1 O2 112.9(2) . . ?
O3 S1 O1 112.9(3) . . ?
O2 S1 O1 111.8(3) . . ?
O3 S1 C1 106.2(3) . . ?
O2 S1 C1 105.6(3) . . ?
O1 S1 C1 106.8(3) . . ?
C7 O6 H6A 109.5 . . ?
C4 O4 H4A 109.5 . . ?
C20 N1 C18 122.4(5) . . ?
C20 N1 H1N 118.8 . . ?
C18 N1 H1N 118.8 . . ?
C15 N2 N3 118.5(5) . . ?
C15 N2 H2N 120.7 . . ?
N3 N2 H2N 120.7 . . ?
O8 N4 O9 123.6(6) . . ?
O8 N4 C8 117.3(5) . . ?
O9 N4 C8 119.1(5) . . ?
C14 N3 N2 113.8(5) . . ?
C20 C21 C16 120.6(6) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
N1 C20 C21 119.1(6) . . ?
N1 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C21 C16 C17 118.8(5) . . ?
C21 C16 C15 117.1(5) . . ?
C17 C16 C15 124.1(5) . . ?
C1 C2 C3 120.2(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C9 C8 C13 123.6(6) . . ?
C9 C8 N4 118.9(5) . . ?
C13 C8 N4 117.6(6) . . ?
C12 C13 C8 117.1(6) . . ?
C12 C13 H13 121.5 . . ?
C8 C13 H13 121.5 . . ?
C2 C3 C4 118.8(6) . . ?
C2 C3 C7 121.4(6) . . ?
C4 C3 C7 119.7(6) . . ?
C5 C6 C1 120.9(6) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C10 C11 C12 120.6(6) . . ?
C10 C11 C14 122.2(6) . . ?
C12 C11 C14 117.0(6) . . ?
O5 C7 O6 122.8(6) . . ?
O5 C7 C3 122.7(6) . . ?
O6 C7 C3 114.5(6) . . ?
O7 C15 N2 124.6(5) . . ?
O7 C15 C16 119.4(5) . . ?
N2 C15 C16 115.9(5) . . ?
C10 C9 C8 118.4(6) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 119.9(6) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C18 C17 C16 119.1(6) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C6 C1 C2 120.0(6) . . ?
C6 C1 S1 120.8(5) . . ?
C2 C1 S1 119.2(5) . . ?
N3 C14 C11 121.7(6) . . ?
N3 C14 H14 119.2 . . ?
C11 C14 H14 119.2 . . ?
N1 C18 C17 119.9(6) . . ?
N1 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
O4 C4 C5 117.2(6) . . ?
O4 C4 C3 122.6(6) . . ?
C5 C4 C3 120.2(6) . . ?
C6 C5 C4 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?

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
C15 N2 N3 C14 178.6(6) . . . . ?
C18 N1 C20 C21 0.6(9) . . . . ?
C16 C21 C20 N1 -1.1(9) . . . . ?
C20 C21 C16 C17 0.7(9) . . . . ?
C20 C21 C16 C15 -175.9(5) . . . . ?
O8 N4 C8 C9 -3.7(8) . . . . ?
O9 N4 C8 C9 175.5(5) . . . . ?
O8 N4 C8 C13 176.0(5) . . . . ?
O9 N4 C8 C13 -4.8(8) . . . . ?
C9 C8 C13 C12 -0.7(9) . . . . ?
N4 C8 C13 C12 179.6(5) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
C1 C2 C3 C7 177.3(5) . . . . ?
C2 C3 C7 O5 -178.2(6) . . . . ?
C4 C3 C7 O5 0.2(9) . . . . ?
C2 C3 C7 O6 -0.7(9) . . . . ?
C4 C3 C7 O6 177.7(6) . . . . ?
N3 N2 C15 O7 8.7(9) . . . . ?
N3 N2 C15 C16 -169.3(5) . . . . ?
C21 C16 C15 O7 2.5(8) . . . . ?
C17 C16 C15 O7 -173.9(6) . . . . ?
C21 C16 C15 N2 -179.4(5) . . . . ?
C17 C16 C15 N2 4.2(8) . . . . ?
C13 C8 C9 C10 0.8(9) . . . . ?
N4 C8 C9 C10 -179.5(5) . . . . ?
C8 C9 C10 C11 -1.0(9) . . . . ?
C12 C11 C10 C9 1.1(9) . . . . ?
C14 C11 C10 C9 175.2(6) . . . . ?
C8 C13 C12 C11 0.7(9) . . . . ?
C10 C11 C12 C13 -1.0(9) . . . . ?
C14 C11 C12 C13 -175.4(6) . . . . ?
C21 C16 C17 C18 0.2(8) . . . . ?
C15 C16 C17 C18 176.5(6) . . . . ?
C5 C6 C1 C2 -0.2(9) . . . . ?
C5 C6 C1 S1 178.8(5) . . . . ?
C3 C2 C1 C6 0.6(9) . . . . ?
C3 C2 C1 S1 -178.4(4) . . . . ?
O3 S1 C1 C6 12.4(6) . . . . ?
O2 S1 C1 C6 132.5(5) . . . . ?
O1 S1 C1 C6 -108.3(5) . . . . ?
O3 S1 C1 C2 -168.7(4) . . . . ?
O2 S1 C1 C2 -48.6(5) . . . . ?
O1 S1 C1 C2 70.6(5) . . . . ?
N2 N3 C14 C11 -172.8(6) . . . . ?
C10 C11 C14 N3 -12.3(10) . . . . ?
C12 C11 C14 N3 162.0(6) . . . . ?
C20 N1 C18 C17 0.3(9) . . . . ?
C16 C17 C18 N1 -0.7(9) . . . . ?
C2 C3 C4 O4 -179.7(5) . . . . ?
C7 C3 C4 O4 1.9(9) . . . . ?
C2 C3 C4 C5 1.2(9) . . . . ?
C7 C3 C4 C5 -177.1(6) . . . . ?
C1 C6 C5 C4 0.4(10) . . . . ?
O4 C4 C5 C6 180.0(6) . . . . ?
C3 C4 C5 C6 -0.9(9) . . . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.135


####################################################################### 
# 
# 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_SHL10
_database_code_depnum_ccdc_archive 'CCDC 2255996'
loop_
_audit_author_name
_audit_author_address
'Aijaz Dar'
;University of Kashmir
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 N4 O7 S'
_chemical_formula_sum            'C21 H16 N4 O7 S'
_chemical_formula_weight         468.44

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'
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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.3934(6)
_cell_length_b                   15.5510(5)
_cell_length_c                   12.4041(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.762(4)
_cell_angle_gamma                90
_cell_volume                     1975.82(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2798
_cell_measurement_theta_min      1.819
_cell_measurement_theta_max      25.000

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   0.132
_exptl_transmission_factor_max   0.254
_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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 D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5466
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.119
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3461
_reflns_number_gt                2798
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0561P)²+1.3306P] 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         3461
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
S1 S 0.24005(7) 0.96667(4) 0.50950(5) 0.0216(2) Uani 1 1 d . . . . .
O3 O 0.18159(19) 1.04056(11) 0.44879(14) 0.0276(5) Uani 1 1 d . . . . .
O1 O 0.36491(19) 0.98798(11) 0.57919(15) 0.0304(5) Uani 1 1 d . . . . .
O4 O 0.3197(2) 0.71243(12) 0.17233(14) 0.0291(5) Uani 1 1 d . . . . .
H4A H 0.317458 0.662987 0.194930 0.044 Uiso 1 1 calc R U . . .
O6 O 0.3087(2) 0.63273(11) 0.49345(14) 0.0313(5) Uani 1 1 d . . . . .
H6A H 0.325136 0.581726 0.505653 0.047 Uiso 1 1 calc R U . . .
O7 O 0.3450(2) 0.46386(11) 0.53619(14) 0.0298(5) Uani 1 1 d . . . . .
O2 O 0.1522(2) 0.92154(11) 0.57051(14) 0.0308(5) Uani 1 1 d . . . . .
O5 O 0.31977(19) 0.59380(11) 0.32109(14) 0.0290(5) Uani 1 1 d . . . . .
N2 N 0.3990(2) 0.47148(12) 0.72215(16) 0.0205(5) Uani 1 1 d . . . . .
H2N H 0.413336 0.443784 0.783019 0.025 Uiso 1 1 calc R U . . .
N3 N 0.4058(2) 0.56021(13) 0.72062(16) 0.0207(5) Uani 1 1 d . . . . .
N1 N 0.3772(2) 0.15691(13) 0.63402(18) 0.0268(5) Uani 1 1 d . . . . .
H1N H 0.379636 0.101636 0.634123 0.032 Uiso 1 1 calc R U . . .
N4 N 0.4641(3) 1.03171(14) 0.86235(19) 0.0362(6) Uani 1 1 d . . . . .
C10 C 0.3719(2) 0.33252(15) 0.6342(2) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.2802(2) 0.80389(15) 0.4383(2) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.273936 0.786943 0.509110 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4509(2) 0.68842(15) 0.82437(19) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.4406(2) 0.59461(15) 0.8152(2) 0.0195(5) Uani 1 1 d . . . . .
H14 H 0.459058 0.560307 0.877307 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3084(3) 0.64903(16) 0.3893(2) 0.0209(6) Uani 1 1 d . . . . .
C18 C 0.4648(3) 0.86556(15) 0.8459(2) 0.0216(6) Uani 1 1 d . . . . .
C13 C 0.3697(3) 0.42948(16) 0.6268(2) 0.0209(6) Uani 1 1 d . . . . .
C4 C 0.3050(3) 0.76841(16) 0.25366(19) 0.0211(6) Uani 1 1 d . . . . .
C6 C 0.2820(3) 0.91595(16) 0.3053(2) 0.0220(6) Uani 1 1 d . . . . .
H6 H 0.277052 0.974002 0.287073 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4614(3) 0.81491(16) 0.9377(2) 0.0227(6) Uani 1 1 d . . . . .
H17 H 0.463618 0.840321 1.005848 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3661(3) 0.28645(16) 0.7300(2) 0.0228(6) Uani 1 1 d . . . . .
H11 H 0.360749 0.315188 0.794817 0.027 Uiso 1 1 calc R U . . .
C1 C 0.2728(3) 0.89024(15) 0.41171(19) 0.0204(6) Uani 1 1 d . . . . .
C3 C 0.2970(2) 0.74170(15) 0.3609(2) 0.0192(5) Uani 1 1 d . . . . .
C16 C 0.4547(2) 0.72636(16) 0.9269(2) 0.0214(6) Uani 1 1 d . . . . .
H16 H 0.452754 0.692072 0.988015 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4556(3) 0.74003(16) 0.7327(2) 0.0221(6) Uani 1 1 d . . . . .
H20 H 0.453889 0.714649 0.664544 0.027 Uiso 1 1 calc R U . . .
C19 C 0.4629(3) 0.82812(16) 0.7427(2) 0.0240(6) Uani 1 1 d . . . . .
H19 H 0.466418 0.862402 0.681864 0.029 Uiso 1 1 calc R U . . .
C21 C 0.4654(3) 0.95826(16) 0.8551(2) 0.0258(6) Uani 1 1 d . . . . .
C5 C 0.2983(3) 0.85567(16) 0.2273(2) 0.0243(6) Uani 1 1 d . . . . .
H5 H 0.304896 0.873264 0.156831 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3823(3) 0.19881(17) 0.5410(2) 0.0263(6) Uani 1 1 d . . . . .
H8 H 0.387239 0.168208 0.477418 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3802(3) 0.28726(16) 0.5390(2) 0.0239(6) Uani 1 1 d . . . . .
H9 H 0.384398 0.316605 0.474391 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3684(3) 0.19811(16) 0.7271(2) 0.0275(6) Uani 1 1 d . . . . .
H12 H 0.363776 0.166828 0.790272 0.033 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
S1 O3 1.4497(18) . ?
S1 O2 1.4607(19) . ?
S1 O1 1.470(2) . ?
S1 C1 1.772(2) . ?
O4 C4 1.360(3) . ?
O4 H4A 0.8200 . ?
O6 C7 1.316(3) . ?
O6 H6A 0.8200 . ?
O7 C13 1.231(3) . ?
O5 C7 1.225(3) . ?
N2 C13 1.341(3) . ?
N2 N3 1.382(3) . ?
N2 H2N 0.8600 . ?
N3 C14 1.284(3) . ?
N1 C8 1.334(3) . ?
N1 C12 1.337(3) . ?
N1 H1N 0.8600 . ?
N4 C21 1.146(3) . ?
C10 C9 1.390(3) . ?
C10 C11 1.397(3) . ?
C10 C13 1.511(3) . ?
C2 C1 1.382(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
C15 C16 1.396(3) . ?
C15 C20 1.400(3) . ?
C15 C14 1.466(3) . ?
C14 H14 0.9300 . ?
C7 C3 1.484(3) . ?
C18 C17 1.390(3) . ?
C18 C19 1.403(4) . ?
C18 C21 1.446(3) . ?
C4 C5 1.395(3) . ?
C4 C3 1.410(3) . ?
C6 C5 1.378(3) . ?
C6 C1 1.398(3) . ?
C6 H6 0.9300 . ?
C17 C16 1.384(3) . ?
C17 H17 0.9300 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C20 C19 1.376(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C5 H5 0.9300 . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C12 H12 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
O3 S1 O2 113.96(12) . . ?
O3 S1 O1 112.17(11) . . ?
O2 S1 O1 111.76(12) . . ?
O3 S1 C1 106.76(11) . . ?
O2 S1 C1 103.99(11) . . ?
O1 S1 C1 107.52(12) . . ?
C4 O4 H4A 109.5 . . ?
C7 O6 H6A 109.5 . . ?
C13 N2 N3 118.6(2) . . ?
C13 N2 H2N 120.7 . . ?
N3 N2 H2N 120.7 . . ?
C14 N3 N2 114.2(2) . . ?
C8 N1 C12 122.1(2) . . ?
C8 N1 H1N 118.9 . . ?
C12 N1 H1N 118.9 . . ?
C9 C10 C11 118.7(2) . . ?
C9 C10 C13 117.1(2) . . ?
C11 C10 C13 124.2(2) . . ?
C1 C2 C3 121.2(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C16 C15 C20 119.9(2) . . ?
C16 C15 C14 118.8(2) . . ?
C20 C15 C14 121.3(2) . . ?
N3 C14 C15 119.4(2) . . ?
N3 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
O5 C7 O6 123.9(2) . . ?
O5 C7 C3 122.0(2) . . ?
O6 C7 C3 114.0(2) . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 C21 120.0(2) . . ?
C19 C18 C21 119.0(2) . . ?
O7 C13 N2 125.1(2) . . ?
O7 C13 C10 119.2(2) . . ?
N2 C13 C10 115.7(2) . . ?
O4 C4 C5 117.2(2) . . ?
O4 C4 C3 122.9(2) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C16 C17 C18 119.5(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C2 C1 C6 119.6(2) . . ?
C2 C1 S1 119.88(19) . . ?
C6 C1 S1 120.41(18) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 C7 121.6(2) . . ?
C4 C3 C7 119.7(2) . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C19 C20 C15 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C20 C19 C18 119.2(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
N4 C21 C18 179.1(3) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C8 C9 120.1(2) . . ?
N1 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
N1 C12 C11 120.3(2) . . ?
N1 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

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
C13 N2 N3 C14 -176.8(2) . . . . ?
N2 N3 C14 C15 -179.8(2) . . . . ?
C16 C15 C14 N3 163.4(2) . . . . ?
C20 C15 C14 N3 -16.0(4) . . . . ?
N3 N2 C13 O7 -1.6(4) . . . . ?
N3 N2 C13 C10 176.5(2) . . . . ?
C9 C10 C13 O7 16.6(4) . . . . ?
C11 C10 C13 O7 -163.4(3) . . . . ?
C9 C10 C13 N2 -161.6(2) . . . . ?
C11 C10 C13 N2 18.3(4) . . . . ?
C19 C18 C17 C16 -0.6(4) . . . . ?
C21 C18 C17 C16 177.0(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C13 C10 C11 C12 179.8(2) . . . . ?
C3 C2 C1 C6 0.1(4) . . . . ?
C3 C2 C1 S1 175.6(2) . . . . ?
C5 C6 C1 C2 0.0(4) . . . . ?
C5 C6 C1 S1 -175.4(2) . . . . ?
O3 S1 C1 C2 -155.0(2) . . . . ?
O2 S1 C1 C2 -34.2(2) . . . . ?
O1 S1 C1 C2 84.5(2) . . . . ?
O3 S1 C1 C6 20.5(2) . . . . ?
O2 S1 C1 C6 141.3(2) . . . . ?
O1 S1 C1 C6 -100.0(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C7 178.5(2) . . . . ?
O4 C4 C3 C2 -179.1(2) . . . . ?
C5 C4 C3 C2 1.1(4) . . . . ?
O4 C4 C3 C7 1.7(4) . . . . ?
C5 C4 C3 C7 -178.1(2) . . . . ?
O5 C7 C3 C2 178.0(2) . . . . ?
O6 C7 C3 C2 -3.7(4) . . . . ?
O5 C7 C3 C4 -2.9(4) . . . . ?
O6 C7 C3 C4 175.4(2) . . . . ?
C18 C17 C16 C15 -0.3(4) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
C14 C15 C16 C17 -178.5(2) . . . . ?
C16 C15 C20 C19 -0.6(4) . . . . ?
C14 C15 C20 C19 178.8(2) . . . . ?
C15 C20 C19 C18 -0.3(4) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C21 C18 C19 C20 -176.7(3) . . . . ?
C1 C6 C5 C4 0.4(4) . . . . ?
O4 C4 C5 C6 179.2(2) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C12 N1 C8 C9 0.8(4) . . . . ?
N1 C8 C9 C10 -0.5(4) . . . . ?
C11 C10 C9 C8 0.2(4) . . . . ?
C13 C10 C9 C8 -179.9(2) . . . . ?
C8 N1 C12 C11 -0.9(4) . . . . ?
C10 C11 C12 N1 0.6(4) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.070


####################################################################### 
# 
# 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_SHL31
_database_code_depnum_ccdc_archive 'CCDC 2255997'
loop_
_audit_author_name
_audit_author_address
'Aijaz Dar'
;University of Kashmir
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br N3 O7 S'
_chemical_formula_sum            'C20 H16 Br N3 O7 S'
_chemical_formula_weight         522.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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      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                   12.189(2)
_cell_length_b                   14.7571(12)
_cell_length_c                   13.783(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.79(2)
_cell_angle_gamma                90
_cell_volume                     2232.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2562
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      66.72
_exptl_crystal_description       blocks
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    3.803
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91468
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4292
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.656
_diffrn_reflns_theta_max         66.727
_diffrn_reflns_theta_full        66.727
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measured_fraction_theta_full 0.760
_diffrn_reflns_Laue_measured_fraction_max 0.760
_diffrn_reflns_Laue_measured_fraction_full 0.760
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_point_group_measured_fraction_full 0.760
_reflns_number_total             3008
_reflns_number_gt                2562
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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-2018/1 (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)+(0.2000P)²] 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         3008
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.1003
_refine_ls_wR_factor_ref         0.3290
_refine_ls_wR_factor_gt          0.2946
_refine_ls_goodness_of_fit_ref   1.451
_refine_ls_restrained_S_all      1.451
_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 0.79696(8) 0.99295(6) 0.30936(7) 0.0485(5) Uani 1 1 d . . . . .
S1 S 0.68502(14) 1.68625(11) 0.33938(11) 0.0311(5) Uani 1 1 d . . . . .
O6 O 0.4483(4) 1.3929(3) 0.1437(3) 0.0325(11) Uani 1 1 d . . . . .
H6 H 0.416758 1.342892 0.125377 0.049 Uiso 1 1 calc R U . . .
O7 O 1.0545(5) 1.4917(3) 0.7340(4) 0.0334(11) Uani 1 1 d . . . . .
O4 O 0.3111(4) 1.5899(4) -0.0936(4) 0.0388(12) Uani 1 1 d . . . . .
H4 H 0.292007 1.536335 -0.096422 0.058 Uiso 1 1 calc R U . . .
O1 O 0.6146(5) 1.7223(3) 0.3950(3) 0.0361(11) Uani 1 1 d . . . . .
O5 O 0.3118(4) 1.4288(3) -0.0231(4) 0.0358(11) Uani 1 1 d . . . . .
O3 O 0.7474(6) 1.6043(4) 0.3876(4) 0.0572(19) Uani 1 1 d . . . . .
N3 N 0.9080(5) 1.4159(4) 0.5401(4) 0.0276(12) Uani 1 1 d . . . . .
N1 N 0.9393(5) 1.8099(4) 0.7301(4) 0.0289(12) Uani 1 1 d . . . . .
H1 H 0.933956 1.866056 0.744264 0.035 Uiso 1 1 calc R U . . .
N2 N 0.9010(6) 1.5054(3) 0.5643(4) 0.0285(13) Uani 1 1 d . . . . .
H2 H 0.850008 1.541261 0.516942 0.034 Uiso 1 1 calc R U . . .
O2 O 0.7633(5) 1.7552(5) 0.3274(4) 0.0498(14) Uani 1 1 d . . . . .
C9 C 0.9579(6) 1.6328(4) 0.6845(4) 0.0261(12) Uani 1 1 d . . . . .
C4 C 0.3961(6) 1.6094(4) 0.0056(5) 0.0283(13) Uani 1 1 d . . . . .
C18 C 0.9149(7) 1.1463(5) 0.4358(5) 0.0368(15) Uani 1 1 d . . . . .
H18 H 0.978479 1.106128 0.472129 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4424(6) 1.5429(5) 0.0886(5) 0.0263(13) Uani 1 1 d . . . . .
C6 C 0.5336(5) 1.5681(4) 0.1881(4) 0.0249(12) Uani 1 1 d . . . . .
H6A H 0.566859 1.524860 0.242275 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8404(6) 1.7684(5) 0.6563(5) 0.0340(14) Uani 1 1 d . . . . .
H7 H 0.766785 1.799309 0.622910 0.041 Uiso 1 1 calc R U . . .
C1 C 0.5753(5) 1.6552(5) 0.2078(5) 0.0277(13) Uani 1 1 d . . . . .
C10 C 1.0580(6) 1.6782(5) 0.7609(4) 0.0294(14) Uani 1 1 d . . . . .
H10 H 1.132301 1.648722 0.796992 0.035 Uiso 1 1 calc R U . . .
C19 C 0.9230(6) 1.2364(4) 0.4683(5) 0.0308(14) Uani 1 1 d . . . . .
H19 H 0.991954 1.256578 0.527638 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9755(6) 1.5360(4) 0.6633(5) 0.0267(13) Uani 1 1 d . . . . .
C14 C 0.8281(6) 1.2965(4) 0.4121(5) 0.0273(13) Uani 1 1 d . . . . .
C13 C 0.8302(6) 1.3910(5) 0.4463(5) 0.0301(14) Uani 1 1 d . . . . .
H13 H 0.775089 1.432683 0.399841 0.036 Uiso 1 1 calc R U . . .
C2 C 0.5294(6) 1.7209(5) 0.1286(5) 0.0336(14) Uani 1 1 d . . . . .
H2A H 0.557484 1.780252 0.143160 0.040 Uiso 1 1 calc R U . . .
C29 C 0.3945(6) 1.4507(5) 0.0653(5) 0.0307(14) Uani 1 1 d . . . . .
C8 C 0.8492(6) 1.6798(4) 0.6306(5) 0.0278(13) Uani 1 1 d . . . . .
H8 H 0.782448 1.651084 0.576935 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4416(6) 1.6975(4) 0.0278(5) 0.0297(13) Uani 1 1 d . . . . .
H3 H 0.412297 1.741186 -0.026135 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0452(6) 1.7679(5) 0.7824(5) 0.0321(14) Uani 1 1 d . . . . .
H11 H 1.111251 1.799088 0.833707 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7167(6) 1.1769(5) 0.2894(5) 0.0332(14) Uani 1 1 d . . . . .
H16 H 0.649212 1.156723 0.228831 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7248(6) 1.2663(5) 0.3216(5) 0.0317(14) Uani 1 1 d . . . . .
H15 H 0.661956 1.306521 0.283341 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8107(6) 1.1176(5) 0.3487(5) 0.0333(14) 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) . ?
S1 O3 1.429(5) . ?
S1 O2 1.453(6) . ?
S1 O1 1.477(5) . ?
S1 C1 1.782(6) . ?
O6 C29 1.307(8) . ?
O6 H6 0.8200 . ?
O7 C12 1.219(8) . ?
O4 C4 1.339(8) . ?
O4 H4 0.8200 . ?
O5 C29 1.240(8) . ?
N3 C13 1.281(8) . ?
N3 N2 1.373(7) . ?
N1 C11 1.327(9) . ?
N1 C7 1.341(9) . ?
N1 H1 0.8600 . ?
N2 C12 1.347(8) . ?
N2 H2 0.8600 . ?
C9 C8 1.389(9) . ?
C9 C10 1.389(9) . ?
C9 C12 1.493(9) . ?
C4 C3 1.394(9) . ?
C4 C5 1.424(8) . ?
C18 C17 1.381(10) . ?
C18 C19 1.393(10) . ?
C18 H18 0.9300 . ?
C5 C6 1.389(9) . ?
C5 C29 1.461(10) . ?
C6 C1 1.365(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.372(10) . ?
C7 H7 0.9300 . ?
C1 C2 1.384(9) . ?
C10 C11 1.379(10) . ?
C10 H10 0.9300 . ?
C19 C14 1.395(9) . ?
C19 H19 0.9300 . ?
C14 C15 1.404(9) . ?
C14 C13 1.469(9) . ?
C13 H13 0.9300 . ?
C2 C3 1.378(9) . ?
C2 H2A 0.9300 . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C16 C15 1.382(10) . ?
C16 C17 1.390(10) . ?
C16 H16 0.9300 . ?
C15 H15 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
O3 S1 O2 113.7(4) . . ?
O3 S1 O1 112.0(4) . . ?
O2 S1 O1 111.5(3) . . ?
O3 S1 C1 105.5(3) . . ?
O2 S1 C1 107.7(3) . . ?
O1 S1 C1 105.8(3) . . ?
C29 O6 H6 109.5 . . ?
C4 O4 H4 109.5 . . ?
C13 N3 N2 115.1(5) . . ?
C11 N1 C7 122.7(6) . . ?
C11 N1 H1 118.7 . . ?
C7 N1 H1 118.7 . . ?
C12 N2 N3 118.8(5) . . ?
C12 N2 H2 120.6 . . ?
N3 N2 H2 120.6 . . ?
C8 C9 C10 118.9(6) . . ?
C8 C9 C12 123.9(6) . . ?
C10 C9 C12 117.1(6) . . ?
O4 C4 C3 118.9(5) . . ?
O4 C4 C5 122.1(6) . . ?
C3 C4 C5 119.0(6) . . ?
C17 C18 C19 118.8(7) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C6 C5 C4 118.5(6) . . ?
C6 C5 C29 122.5(6) . . ?
C4 C5 C29 119.0(6) . . ?
C1 C6 C5 121.1(5) . . ?
C1 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
N1 C7 C8 119.1(6) . . ?
N1 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C6 C1 C2 121.0(6) . . ?
C6 C1 S1 119.6(5) . . ?
C2 C1 S1 119.3(5) . . ?
C11 C10 C9 118.8(6) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C18 C19 C14 120.1(6) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O7 C12 N2 125.5(6) . . ?
O7 C12 C9 119.2(6) . . ?
N2 C12 C9 115.3(5) . . ?
C19 C14 C15 119.9(6) . . ?
C19 C14 C13 122.1(6) . . ?
C15 C14 C13 118.0(6) . . ?
N3 C13 C14 119.9(6) . . ?
N3 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
O5 C29 O6 123.0(6) . . ?
O5 C29 C5 122.3(6) . . ?
O6 C29 C5 114.7(6) . . ?
C7 C8 C9 120.1(6) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N1 C11 C10 120.4(6) . . ?
N1 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C15 C16 C17 119.1(6) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C15 C14 119.9(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C18 C17 C16 122.0(7) . . ?
C18 C17 Br1 118.5(5) . . ?
C16 C17 Br1 119.5(5) . . ?

_refine_diff_density_max         1.335
_refine_diff_density_min         -1.340
_refine_diff_density_rms         0.190




