# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_hb125m
_database_code_depnum_ccdc_archive 'CCDC 2006459'
loop_
_audit_author_name
_audit_author_address
'Jerome Marrot'
;Institut Lavoisier de Versailles
France
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2020-07-30 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         ?
_chemical_formula_sum            'C21 H12 O3 S'
_chemical_formula_weight         344.37

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   3.8428(3)
_cell_length_b                   36.328(3)
_cell_length_c                   11.0693(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.930(4)
_cell_angle_gamma                90
_cell_volume                     1544.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8803
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.11

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.6649
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014/2)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26043
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.841
_diffrn_reflns_theta_max         30.263
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4086
_reflns_number_gt                3328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.865
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1200P)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 
; 
 Flack x determined using 1304 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4086
_refine_ls_number_parameters     228
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.1678(2) 0.33603(3) 0.35197(10) 0.0316(3) Uani 1 1 d . . . . .
O1 O -0.1686(11) 0.45917(10) 0.7806(4) 0.0570(10) Uani 1 1 d . . . . .
O2 O 0.0444(13) 0.26411(10) 0.2261(4) 0.0584(10) Uani 1 1 d . . . . .
O3 O 0.2783(10) 0.28086(9) 0.0519(3) 0.0438(8) Uani 1 1 d . . . . .
C1 C 0.3212(10) 0.38054(11) 0.3335(4) 0.0297(8) Uani 1 1 d . . . . .
C2 C 0.2997(11) 0.41083(11) 0.4164(4) 0.0299(8) Uani 1 1 d . . . . .
C3 C 0.1837(10) 0.41019(11) 0.5375(4) 0.0293(8) Uani 1 1 d . . . . .
C4 C 0.1227(10) 0.38050(11) 0.6271(3) 0.0298(8) Uani 1 1 d . . . . .
C5 C 0.2153(13) 0.34364(12) 0.6348(4) 0.0369(10) Uani 1 1 d . . . . .
H5 H 0.331762 0.332720 0.571752 0.044 Uiso 1 1 calc R U . . .
C6 C 0.1358(14) 0.32286(14) 0.7357(4) 0.0433(11) Uani 1 1 d . . . . .
H6 H 0.194455 0.298028 0.738504 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0319(17) 0.33887(16) 0.8334(5) 0.0501(13) Uani 1 1 d . . . . .
H7 H -0.092784 0.324615 0.899232 0.060 Uiso 1 1 calc R U . . .
C8 C -0.1053(14) 0.37614(15) 0.8305(4) 0.0459(12) Uani 1 1 d . . . . .
H8 H -0.206269 0.387465 0.895992 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0279(11) 0.39622(13) 0.7300(4) 0.0355(9) Uani 1 1 d . . . . .
C10 C -0.0504(13) 0.43664(12) 0.7116(5) 0.0398(10) Uani 1 1 d . . . . .
C11 C 0.1041(11) 0.44375(12) 0.5930(4) 0.0346(9) Uani 1 1 d . . . . .
C12 C 0.1666(14) 0.47795(12) 0.5414(5) 0.0422(11) Uani 1 1 d . . . . .
H12 H 0.101933 0.499558 0.579689 0.051 Uiso 1 1 calc R U . . .
C13 C 0.3242(13) 0.47886(12) 0.4340(5) 0.0424(11) Uani 1 1 d . . . . .
H13 H 0.390859 0.501413 0.402409 0.051 Uiso 1 1 calc R U . . .
C14 C 0.3899(11) 0.44630(12) 0.3686(4) 0.0357(9) Uani 1 1 d . . . . .
C15 C 0.5315(13) 0.44940(13) 0.2518(4) 0.0409(11) Uani 1 1 d . . . . .
H15 H 0.605703 0.472332 0.225578 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5613(13) 0.42001(14) 0.1776(5) 0.0421(10) Uani 1 1 d . . . . .
H16 H 0.658245 0.422642 0.102238 0.051 Uiso 1 1 calc R U . . .
C17 C 0.4420(11) 0.38499(12) 0.2167(4) 0.0346(9) Uani 1 1 d . . . . .
C18 C 0.4143(12) 0.35234(13) 0.1460(4) 0.0372(10) Uani 1 1 d . . . . .
H18 H 0.486191 0.350631 0.066847 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2709(11) 0.32385(12) 0.2072(4) 0.0312(8) Uani 1 1 d . . . . .
C20 C 0.1846(12) 0.28648(12) 0.1645(4) 0.0346(9) Uani 1 1 d . . . . .
C21 C 0.1818(17) 0.24568(15) -0.0002(5) 0.0523(13) Uani 1 1 d . . . . .
H21A H -0.067153 0.243350 -0.003104 0.079 Uiso 1 1 calc R U . . .
H21B H 0.281798 0.226260 0.048441 0.079 Uiso 1 1 calc R U . . .
H21C H 0.266771 0.244080 -0.080614 0.079 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 C19 1.722(4) . ?
S1 C1 1.736(4) . ?
O1 C10 1.218(6) . ?
O2 C20 1.200(6) . ?
O3 C20 1.325(5) . ?
O3 C21 1.445(6) . ?
C1 C17 1.397(6) . ?
C1 C2 1.437(6) . ?
C2 C3 1.428(6) . ?
C2 C14 1.440(6) . ?
C3 C11 1.403(6) . ?
C3 C4 1.489(6) . ?
C4 C5 1.387(6) . ?
C4 C9 1.415(5) . ?
C5 C6 1.391(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.404(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.484(6) . ?
C10 C11 1.482(7) . ?
C11 C12 1.391(7) . ?
C12 C13 1.353(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.424(7) . ?
C15 C16 1.354(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.425(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.423(7) . ?
C18 C19 1.363(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.471(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C19 S1 C1 92.3(2) . . ?
C20 O3 C21 116.0(4) . . ?
C17 C1 C2 122.0(4) . . ?
C17 C1 S1 110.0(3) . . ?
C2 C1 S1 127.7(3) . . ?
C3 C2 C1 127.9(4) . . ?
C3 C2 C14 116.5(4) . . ?
C1 C2 C14 115.5(4) . . ?
C11 C3 C2 118.4(4) . . ?
C11 C3 C4 107.2(4) . . ?
C2 C3 C4 134.3(4) . . ?
C5 C4 C9 116.9(4) . . ?
C5 C4 C3 133.9(4) . . ?
C9 C4 C3 108.7(4) . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 119.1(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 122.9(4) . . ?
C8 C9 C10 128.6(4) . . ?
C4 C9 C10 108.2(4) . . ?
O1 C10 C11 127.4(5) . . ?
O1 C10 C9 126.9(5) . . ?
C11 C10 C9 105.7(4) . . ?
C12 C11 C3 123.6(4) . . ?
C12 C11 C10 126.8(4) . . ?
C3 C11 C10 109.6(4) . . ?
C13 C12 C11 118.1(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C14 121.5(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 118.6(4) . . ?
C13 C14 C2 120.7(4) . . ?
C15 C14 C2 120.6(4) . . ?
C16 C15 C14 122.1(4) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.0(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C1 C17 C18 113.0(4) . . ?
C1 C17 C16 120.3(4) . . ?
C18 C17 C16 126.6(4) . . ?
C19 C18 C17 112.6(4) . . ?
C19 C18 H18 123.7 . . ?
C17 C18 H18 123.7 . . ?
C18 C19 C20 129.2(4) . . ?
C18 C19 S1 112.1(3) . . ?
C20 C19 S1 118.7(3) . . ?
O2 C20 O3 124.9(4) . . ?
O2 C20 C19 122.9(4) . . ?
O3 C20 C19 112.3(4) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         1.111
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.092

