# 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_AB_02_0m
_database_code_depnum_ccdc_archive 'CCDC 2259946'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2023-04-30 deposited with the CCDC.	2023-08-21 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            'C16 H16 O2 S'
_chemical_formula_weight         272.35

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.3670(4)
_cell_length_b                   5.5115(2)
_cell_length_c                   12.1835(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.746(2)
_cell_angle_gamma                90
_cell_volume                     692.64(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      2.4613
_cell_measurement_theta_max      33.1426

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            22252
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         33.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5306
_reflns_number_gt                4738
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.994

_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       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1460 (Hübschle et al., 2011)
;
_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)+(0.0644P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 1973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5306
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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 0.37985(4) 0.50978(9) 0.26086(4) 0.02902(11) Uani 1 1 d . . . . .
O1 O 0.27074(14) 0.4046(3) 0.19543(14) 0.0426(4) Uani 1 1 d . . . . .
O2 O 0.37054(17) 0.7562(3) 0.29889(17) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.41942(18) 0.3196(4) 0.37953(16) 0.0304(3) Uani 1 1 d . . . . .
H1A H 0.446895 0.157930 0.355218 0.037 Uiso 1 1 calc R U . . .
H1B H 0.492668 0.391971 0.426839 0.037 Uiso 1 1 calc R U . . .
C2 C 0.30487(18) 0.2919(3) 0.44490(16) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.245785 0.162877 0.426732 0.037 Uiso 1 1 calc R U . . .
C3 C 0.28262(17) 0.4394(3) 0.52681(15) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.345558 0.561958 0.545199 0.035 Uiso 1 1 calc R U . . .
C4 C 0.17071(16) 0.4338(3) 0.59239(13) 0.0252(3) Uani 1 1 d . . . . .
C5 C 0.07923(17) 0.2465(3) 0.58527(14) 0.0272(3) Uani 1 1 d . . . . .
H5 H 0.089159 0.112425 0.537868 0.033 Uiso 1 1 calc R U . . .
C6 C -0.02596(18) 0.2558(4) 0.64713(16) 0.0318(4) Uani 1 1 d . . . . .
H6 H -0.087093 0.126899 0.642524 0.038 Uiso 1 1 calc R U . . .
C7 C -0.04257(19) 0.4529(4) 0.71599(15) 0.0340(4) Uani 1 1 d . . . . .
H7 H -0.115574 0.460485 0.757181 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0487(2) 0.6380(4) 0.72373(17) 0.0357(4) Uani 1 1 d . . . . .
H8 H 0.038395 0.772432 0.770874 0.043 Uiso 1 1 calc R U . . .
C9 C 0.15467(19) 0.6281(3) 0.66325(16) 0.0313(4) Uani 1 1 d . . . . .
H9 H 0.217110 0.754751 0.670010 0.038 Uiso 1 1 calc R U . . .
C10 C 0.51760(15) 0.4858(3) 0.18792(13) 0.0250(3) Uani 1 1 d . . . . .
C11 C 0.53013(18) 0.2886(3) 0.11823(16) 0.0306(3) Uani 1 1 d . . . . .
H11 H 0.465679 0.165519 0.110778 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6384(2) 0.2746(4) 0.05978(15) 0.0331(4) Uani 1 1 d . . . . .
H12 H 0.647751 0.140209 0.012414 0.040 Uiso 1 1 calc R U . . .
C13 C 0.73340(19) 0.4543(4) 0.06943(14) 0.0314(4) Uani 1 1 d . . . . .
C14 C 0.71959(18) 0.6483(4) 0.14115(16) 0.0309(3) Uani 1 1 d . . . . .
H14 H 0.784484 0.770437 0.149484 0.037 Uiso 1 1 calc R U . . .
C15 C 0.61245(17) 0.6649(3) 0.20030(15) 0.0275(3) Uani 1 1 d . . . . .
H15 H 0.603893 0.797424 0.248889 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8477(3) 0.4434(6) 0.00250(19) 0.0498(6) Uani 1 1 d . . . . .
H16A H 0.857198 0.277813 -0.024897 0.075 Uiso 1 1 calc R U . . .
H16B H 0.926506 0.489900 0.048870 0.075 Uiso 1 1 calc R U . . .
H16C H 0.833721 0.555309 -0.060064 0.075 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 O1 1.4388(16) . ?
S1 O2 1.4415(16) . ?
S1 C10 1.7609(17) . ?
S1 C1 1.7994(19) . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.325(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.473(2) . ?
C3 H3 0.9500 . ?
C4 C9 1.396(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.391(2) . ?
C10 C11 1.393(2) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C13 C16 1.505(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
O1 S1 O2 118.91(11) . . ?
O1 S1 C10 108.81(9) . . ?
O2 S1 C10 108.46(9) . . ?
O1 S1 C1 108.29(10) . . ?
O2 S1 C1 107.92(11) . . ?
C10 S1 C1 103.33(8) . . ?
C2 C1 S1 110.89(12) . . ?
C2 C1 H1A 109.5 . . ?
S1 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 122.89(17) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 C3 C4 126.95(17) . . ?
C2 C3 H3 116.5 . . ?
C4 C3 H3 116.5 . . ?
C9 C4 C5 118.85(16) . . ?
C9 C4 C3 117.92(16) . . ?
C5 C4 C3 123.22(16) . . ?
C6 C5 C4 120.28(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.46(17) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 119.28(18) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 120.45(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 120.66(17) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C15 C10 C11 120.78(16) . . ?
C15 C10 S1 119.50(13) . . ?
C11 C10 S1 119.72(13) . . ?
C12 C11 C10 118.98(16) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.17(17) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 118.74(17) . . ?
C12 C13 C16 120.9(2) . . ?
C14 C13 C16 120.3(2) . . ?
C15 C14 C13 120.88(17) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 119.44(16) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 S1 C1 C2 -57.36(16) . . . . ?
O2 S1 C1 C2 72.59(16) . . . . ?
C10 S1 C1 C2 -172.66(13) . . . . ?
S1 C1 C2 C3 -90.8(2) . . . . ?
C1 C2 C3 C4 177.17(16) . . . . ?
C2 C3 C4 C9 -170.03(19) . . . . ?
C2 C3 C4 C5 8.7(3) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -178.18(16) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C4 0.9(3) . . . . ?
C5 C4 C9 C8 -1.3(3) . . . . ?
C3 C4 C9 C8 177.43(17) . . . . ?
O1 S1 C10 C15 147.56(14) . . . . ?
O2 S1 C10 C15 16.85(17) . . . . ?
C1 S1 C10 C15 -97.51(15) . . . . ?
O1 S1 C10 C11 -32.19(16) . . . . ?
O2 S1 C10 C11 -162.90(15) . . . . ?
C1 S1 C10 C11 82.74(15) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
S1 C10 C11 C12 178.89(14) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C11 C12 C13 C16 -177.52(18) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C16 C13 C14 C15 177.69(18) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
S1 C10 C15 C14 -178.72(13) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_AB_03_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2259947'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2023-04-30 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT094_AB_03_2_0m          
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.11 Report
RESPONSE: There remains unknown density in the crystal. Attempts to identify
this density as chlorine, oxygen, carbon, and nitrogen were made however no
solution appeared as reasonable. The small percentage of this disorder does
complicate the solution and model. Based on our attempts, it appears to be a
chlorine atom but we cannot definitively make this claim.
;
_vrf_PLAT097_AB_03_2_0m          
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.23 eA-3  
RESPONSE: There remains unknown density in the crystal. Attempts to identify
this density as chlorine, oxygen, carbon, and nitrogen were made however no
solution appeared as reasonable. The small percentage of this disorder does
complicate the solution and model. Based on our attempts, it appears to be a
chlorine atom but we cannot definitively make this claim.
;

_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            'C16 H15 Cl O3 S'
_chemical_formula_weight         322.79

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5988(4)
_cell_length_b                   7.6069(4)
_cell_length_c                   13.6966(7)
_cell_angle_alpha                91.485(3)
_cell_angle_beta                 95.543(3)
_cell_angle_gamma                108.404(3)
_cell_volume                     746.37(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9831
_cell_measurement_theta_min      2.8265
_cell_measurement_theta_max      33.1850

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.402
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            32913
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         33.217
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5696
_reflns_number_gt                4696
_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       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1460 (Hübschle et al., 2011)
;
_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)+(0.0742P)²+0.6132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5696
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.17908(7) 0.80142(7) 0.93005(3) 0.03737(12) Uani 1 1 d . . . . .
S1 S 0.75314(5) 1.01246(5) 0.62171(3) 0.02368(10) Uani 1 1 d . . . . .
O1 O 0.94110(18) 1.06304(19) 0.66987(10) 0.0332(3) Uani 1 1 d . . . . .
O2 O 0.70506(19) 1.14119(17) 0.55699(10) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.3566(2) 0.2986(2) 0.90571(10) 0.0371(3) Uani 1 1 d . . . . .
C1 C 0.7057(2) 0.7995(2) 0.54908(12) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.570044 0.750063 0.527823 0.032 Uiso 1 1 calc R U . . .
H1B H 0.770691 0.826517 0.489278 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7645(2) 0.6520(2) 0.60138(12) 0.0263(3) Uani 1 1 d . . . . .
C3 C 0.9198(3) 0.6195(3) 0.58009(15) 0.0360(4) Uani 1 1 d . . . . .
H3A H 0.960747 0.529494 0.613882 0.043 Uiso 1 1 calc R U . . .
H3B H 0.989239 0.686285 0.531160 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6505(2) 0.5516(2) 0.67722(12) 0.0242(3) Uani 1 1 d . . . . .
C5 C 0.7378(2) 0.5036(2) 0.76260(13) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.869303 0.529912 0.769615 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6366(3) 0.4188(2) 0.83677(13) 0.0313(3) Uani 1 1 d . . . . .
H6 H 0.698627 0.387774 0.894078 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4433(3) 0.3789(2) 0.82737(13) 0.0288(3) Uani 1 1 d . . . . .
C8 C 0.3528(2) 0.4209(2) 0.74255(13) 0.0283(3) Uani 1 1 d . . . . .
H8 H 0.220774 0.390485 0.734820 0.034 Uiso 1 1 calc R U . . .
C9 C 0.4571(2) 0.5080(2) 0.66881(12) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.394656 0.538339 0.611417 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1625(3) 0.2725(3) 0.90324(17) 0.0429(5) Uani 1 1 d . . . . .
H10A H 0.141783 0.393207 0.901083 0.064 Uiso 1 1 calc R U . . .
H10B H 0.116154 0.212018 0.962237 0.064 Uiso 1 1 calc R U . . .
H10C H 0.095669 0.194290 0.844702 0.064 Uiso 1 1 calc R U . . .
C11 C 0.5964(2) 0.9627(2) 0.71185(11) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.6528(2) 0.9199(2) 0.80568(12) 0.0260(3) Uani 1 1 d . . . . .
H12 H 0.778384 0.924405 0.822888 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5242(2) 0.8706(2) 0.87376(12) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.559789 0.840273 0.937927 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3423(2) 0.8667(2) 0.84580(12) 0.0267(3) Uani 1 1 d . . . . .
C15 C 0.2845(2) 0.9105(3) 0.75307(13) 0.0297(3) Uani 1 1 d . . . . .
H15 H 0.159291 0.907441 0.736253 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4139(2) 0.9588(2) 0.68541(12) 0.0278(3) Uani 1 1 d . . . . .
H16 H 0.377906 0.989128 0.621321 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
Cl1 C14 1.7417(17) . ?
S1 O1 1.4426(13) . ?
S1 O2 1.4444(12) . ?
S1 C11 1.7638(17) . ?
S1 C1 1.7952(17) . ?
O3 C7 1.370(2) . ?
O3 C10 1.422(3) . ?
C1 C2 1.506(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.337(3) . ?
C2 C4 1.487(2) . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C4 C9 1.393(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(2) . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.390(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
O1 S1 O2 118.34(8) . . ?
O1 S1 C11 108.74(8) . . ?
O2 S1 C11 108.39(8) . . ?
O1 S1 C1 108.52(8) . . ?
O2 S1 C1 106.27(8) . . ?
C11 S1 C1 105.88(8) . . ?
C7 O3 C10 117.08(16) . . ?
C2 C1 S1 114.33(11) . . ?
C2 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C4 122.29(16) . . ?
C3 C2 C1 119.02(15) . . ?
C4 C2 C1 118.66(15) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C9 C4 C5 117.64(15) . . ?
C9 C4 C2 122.30(15) . . ?
C5 C4 C2 120.02(15) . . ?
C6 C5 C4 121.43(16) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.92(16) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O3 C7 C8 124.77(17) . . ?
O3 C7 C6 115.38(16) . . ?
C8 C7 C6 119.85(15) . . ?
C7 C8 C9 119.50(16) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C8 121.63(15) . . ?
C4 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.21(15) . . ?
C16 C11 S1 118.25(12) . . ?
C12 C11 S1 120.48(12) . . ?
C13 C12 C11 119.54(15) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 118.40(14) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 122.71(16) . . ?
C15 C14 Cl1 118.55(14) . . ?
C13 C14 Cl1 118.73(12) . . ?
C14 C15 C16 118.45(16) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 119.69(15) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?

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
O1 S1 C1 C2 46.17(14) . . . . ?
O2 S1 C1 C2 174.44(12) . . . . ?
C11 S1 C1 C2 -70.42(14) . . . . ?
S1 C1 C2 C3 -103.50(18) . . . . ?
S1 C1 C2 C4 74.68(17) . . . . ?
C3 C2 C4 C9 -146.53(18) . . . . ?
C1 C2 C4 C9 35.3(2) . . . . ?
C3 C2 C4 C5 35.9(2) . . . . ?
C1 C2 C4 C5 -142.23(16) . . . . ?
C9 C4 C5 C6 -1.1(2) . . . . ?
C2 C4 C5 C6 176.61(16) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C10 O3 C7 C8 -6.1(3) . . . . ?
C10 O3 C7 C6 173.97(17) . . . . ?
C5 C6 C7 O3 -178.66(16) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
O3 C7 C8 C9 178.07(16) . . . . ?
C6 C7 C8 C9 -2.0(3) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C2 C4 C9 C8 -177.18(15) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
O1 S1 C11 C16 163.27(13) . . . . ?
O2 S1 C11 C16 33.39(15) . . . . ?
C1 S1 C11 C16 -80.29(14) . . . . ?
O1 S1 C11 C12 -19.69(15) . . . . ?
O2 S1 C11 C12 -149.57(13) . . . . ?
C1 S1 C11 C12 96.75(14) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
S1 C11 C12 C13 -176.28(12) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 Cl1 178.99(12) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
Cl1 C14 C15 C16 -178.73(13) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
S1 C11 C16 C15 176.61(13) . . . . ?

_refine_diff_density_max         2.229
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.077

