# 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 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2000213'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap'
;University of Delhi
India
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 O5 S'
_chemical_formula_sum            'C15 H10 O5 S'
_chemical_formula_weight         302.29

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   13.2481(4)
_cell_length_b                   8.2931(3)
_cell_length_c                   12.1623(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1336.25(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4184
_cell_measurement_theta_min      3.9250
_cell_measurement_theta_max      24.5350

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.261
_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  'xcalibur sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18574
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.502
_diffrn_reflns_theta_max         29.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3407
_reflns_number_gt                2556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.875
_reflns_Friedel_fraction_full    0.998

_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       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0926P)²+3.1416P] 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 955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3407
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   0.648
_refine_ls_restrained_S_all      0.648
_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 0.89902(8) 0.69007(16) 0.39069(12) 0.0491(3) Uani 1 1 d . . . . .
O1 O 0.6465(2) 0.4839(4) 0.5827(3) 0.0456(8) Uani 1 1 d . . . . .
O5 O 0.9309(3) 0.8865(5) 0.1918(3) 0.0614(10) Uani 1 1 d . . . . .
O4 O 0.7669(3) 0.9139(5) 0.1444(3) 0.0634(11) Uani 1 1 d . . . . .
O2 O 0.5367(2) 0.5995(5) 0.4713(4) 0.0653(11) Uani 1 1 d . . . . .
O3 O 0.6291(3) 0.7779(5) 0.2819(3) 0.0631(11) Uani 1 1 d . . . . .
H9 H 0.645029 0.830231 0.227339 0.095 Uiso 1 1 calc R U . . .
C6 C 0.7424(3) 0.3469(6) 0.7167(4) 0.0391(9) Uani 1 1 d . . . . .
C12 C 0.7124(3) 0.7318(6) 0.3355(4) 0.0421(10) Uani 1 1 d . . . . .
C8 C 0.8235(3) 0.5118(6) 0.5667(4) 0.0415(10) Uani 1 1 d . . . . .
H8 H 0.888408 0.492242 0.592446 0.050 Uiso 1 1 calc R U . . .
C9 C 0.8073(3) 0.6063(6) 0.4719(4) 0.0387(9) Uani 1 1 d . . . . .
C7 C 0.7422(3) 0.4505(6) 0.6191(4) 0.0388(10) Uani 1 1 d . . . . .
C14 C 0.8319(4) 0.8631(6) 0.2059(4) 0.0499(12) Uani 1 1 d . . . . .
C11 C 0.6246(3) 0.5779(6) 0.4916(4) 0.0428(11) Uani 1 1 d . . . . .
C13 C 0.8092(4) 0.7702(6) 0.3034(4) 0.0439(10) Uani 1 1 d . . . . .
C10 C 0.7110(3) 0.6385(6) 0.4326(4) 0.0392(9) Uani 1 1 d . . . . .
C2 C 0.6536(5) 0.2090(7) 0.8615(5) 0.0565(14) Uani 1 1 d . . . . .
H2 H 0.593346 0.183479 0.896550 0.068 Uiso 1 1 calc R U . . .
C1 C 0.6526(4) 0.3059(6) 0.7698(4) 0.0484(11) Uani 1 1 d . . . . .
H1 H 0.591438 0.344568 0.742909 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8324(4) 0.2852(7) 0.7578(5) 0.0547(13) Uani 1 1 d . . . . .
H5 H 0.892997 0.309861 0.723152 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7433(5) 0.1493(6) 0.9018(5) 0.0601(14) Uani 1 1 d . . . . .
H3 H 0.743770 0.083535 0.963723 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8323(5) 0.1880(7) 0.8494(5) 0.0608(15) Uani 1 1 d . . . . .
H4 H 0.893058 0.147985 0.876302 0.073 Uiso 1 1 calc R U . . .
C15 C 0.9602(6) 0.9804(8) 0.0969(6) 0.0759(18) Uani 1 1 d . . . . .
H12 H 1.032424 0.989703 0.094654 0.114 Uiso 1 1 calc R U . . .
H11 H 0.936923 0.927962 0.031249 0.114 Uiso 1 1 calc R U . . .
H10 H 0.930792 1.085971 0.101686 0.114 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 C9 1.714(5) . ?
S1 C13 1.728(5) . ?
O1 C7 1.371(5) . ?
O1 C11 1.386(6) . ?
O5 C14 1.337(7) . ?
O5 C15 1.447(7) . ?
O4 C14 1.216(7) . ?
O2 C11 1.204(5) . ?
O3 C12 1.338(6) . ?
O3 H9 0.8200 . ?
C6 C5 1.390(7) . ?
C6 C1 1.396(7) . ?
C6 C7 1.465(6) . ?
C12 C13 1.378(7) . ?
C12 C10 1.412(6) . ?
C8 C7 1.351(6) . ?
C8 C9 1.410(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(6) . ?
C14 C13 1.445(7) . ?
C11 C10 1.442(6) . ?
C2 C1 1.375(7) . ?
C2 C3 1.377(8) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C5 C4 1.375(7) . ?
C5 H5 0.9300 . ?
C3 C4 1.379(8) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C15 H12 0.9600 . ?
C15 H11 0.9600 . ?
C15 H10 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
C9 S1 C13 91.2(2) . . ?
C7 O1 C11 124.5(4) . . ?
C14 O5 C15 116.4(5) . . ?
C12 O3 H9 109.5 . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 C7 120.6(4) . . ?
C1 C6 C7 121.1(4) . . ?
O3 C12 C13 124.3(5) . . ?
O3 C12 C10 123.7(5) . . ?
C13 C12 C10 112.1(4) . . ?
C7 C8 C9 118.3(4) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 S1 112.0(4) . . ?
C8 C9 S1 126.1(3) . . ?
C8 C7 O1 120.5(4) . . ?
C8 C7 C6 127.0(4) . . ?
O1 C7 C6 112.5(4) . . ?
O4 C14 O5 124.5(5) . . ?
O4 C14 C13 122.8(5) . . ?
O5 C14 C13 112.7(5) . . ?
O2 C11 O1 116.8(4) . . ?
O2 C11 C10 127.9(5) . . ?
O1 C11 C10 115.3(4) . . ?
C12 C13 C14 123.3(5) . . ?
C12 C13 S1 112.2(4) . . ?
C14 C13 S1 124.4(4) . . ?
C9 C10 C12 112.5(4) . . ?
C9 C10 C11 119.4(4) . . ?
C12 C10 C11 128.1(4) . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C1 C6 120.6(5) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C4 C3 C2 119.3(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O5 C15 H12 109.5 . . ?
O5 C15 H11 109.5 . . ?
H12 C15 H11 109.5 . . ?
O5 C15 H10 109.5 . . ?
H12 C15 H10 109.5 . . ?
H11 C15 H10 109.5 . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040

