# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 1974746'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap' 'University of Delhi'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2024-06-05 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         'C16 H13 Cl N2 O S'
_chemical_formula_sum            'C16 H13 Cl N2 O S'
_chemical_formula_weight         316.79

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'
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'
Cl Cl 0.1484 0.1585 '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                   10.9847(6)
_cell_length_b                   9.3266(4)
_cell_length_c                   15.3230(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.140(6)
_cell_angle_gamma                90
_cell_volume                     1500.12(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4532
_cell_measurement_theta_min      3.5120
_cell_measurement_theta_max      24.2410

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             656
_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    0.393
_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            18167
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.474
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2626
_reflns_number_gt                2064
_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       '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)+(0.0447P)²+0.8316P] 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         2626
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
S1 S 0.86270(7) 0.73786(8) 0.38110(5) 0.0566(2) Uani 1 1 d . . . . .
Cl Cl 0.47940(7) 0.29810(9) 0.50701(6) 0.0746(3) Uani 1 1 d . . . . .
O1 O 1.0116(2) 0.7515(2) 0.66453(14) 0.0711(6) Uani 1 1 d . . . . .
N1 N 0.9184(2) 0.4998(2) 0.69275(13) 0.0549(6) Uani 1 1 d . . . . .
H1A H 0.908423 0.427391 0.724745 0.066 Uiso 1 1 calc R U . . .
H1B H 0.963466 0.571761 0.718866 0.066 Uiso 1 1 calc R U . . .
N2 N 0.7723(3) 0.1700(3) 0.66269(16) 0.0659(7) Uani 1 1 d . . . . .
C8 C 0.7889(2) 0.3811(2) 0.55909(16) 0.0414(6) Uani 1 1 d . . . . .
C11 C 0.8238(2) 0.6060(2) 0.45053(16) 0.0404(6) Uani 1 1 d . . . . .
C9 C 0.8628(2) 0.5004(2) 0.60091(16) 0.0412(6) Uani 1 1 d . . . . .
C10 C 0.8727(2) 0.6197(2) 0.54617(16) 0.0391(5) Uani 1 1 d . . . . .
C7 C 0.7326(2) 0.3755(2) 0.46503(16) 0.0404(6) Uani 1 1 d . . . . .
C5 C 0.6584(2) 0.2488(3) 0.42032(16) 0.0445(6) Uani 1 1 d . . . . .
C12 C 0.7542(2) 0.4859(3) 0.41164(16) 0.0444(6) Uani 1 1 d . . . . .
H12 H 0.721631 0.479701 0.348444 0.053 Uiso 1 1 calc R U . . .
C13 C 0.9285(2) 0.7537(3) 0.59170(18) 0.0466(6) Uani 1 1 d . . . . .
C6 C 0.5478(2) 0.2008(3) 0.43728(18) 0.0492(6) Uani 1 1 d . . . . .
C15 C 0.7780(3) 0.2626(3) 0.61571(17) 0.0488(6) Uani 1 1 d . . . . .
C4 C 0.6986(3) 0.1744(3) 0.35542(18) 0.0563(7) Uani 1 1 d . . . . .
H4 H 0.770093 0.206244 0.340379 0.068 Uiso 1 1 calc R U . . .
C1 C 0.4865(3) 0.0781(3) 0.3963(2) 0.0610(8) Uani 1 1 d . . . . .
H1 H 0.414848 0.045232 0.410687 0.073 Uiso 1 1 calc R U . . .
C2 C 0.5308(3) 0.0050(3) 0.3347(2) 0.0676(8) Uani 1 1 d . . . . .
H2 H 0.489978 -0.078248 0.307835 0.081 Uiso 1 1 calc R U . . .
C3 C 0.6349(3) 0.0542(3) 0.3126(2) 0.0664(8) Uani 1 1 d . . . . .
H3 H 0.663010 0.006681 0.268776 0.080 Uiso 1 1 calc R U . . .
C16 C 0.7612(3) 0.6988(3) 0.26967(18) 0.0660(8) Uani 1 1 d . . . . .
H16A H 0.776487 0.766677 0.226960 0.099 Uiso 1 1 calc R U . . .
H16B H 0.778559 0.603740 0.252487 0.099 Uiso 1 1 calc R U . . .
H16C H 0.673912 0.705005 0.269479 0.099 Uiso 1 1 calc R U . . .
C14 C 0.8712(4) 0.8966(3) 0.5567(2) 0.0746(9) Uani 1 1 d . . . . .
H14A H 0.807262 0.883707 0.499078 0.112 Uiso 1 1 calc R U . . .
H14B H 0.833078 0.937991 0.599729 0.112 Uiso 1 1 calc R U . . .
H14C H 0.936557 0.959224 0.548962 0.112 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 C11 1.759(2) . ?
S1 C16 1.780(3) . ?
Cl C6 1.733(3) . ?
O1 C13 1.216(3) . ?
N1 C9 1.359(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C15 1.138(3) . ?
C8 C7 1.392(3) . ?
C8 C9 1.414(3) . ?
C8 C15 1.432(3) . ?
C11 C12 1.388(3) . ?
C11 C10 1.410(3) . ?
C9 C10 1.417(3) . ?
C10 C13 1.474(3) . ?
C7 C12 1.378(3) . ?
C7 C5 1.483(3) . ?
C5 C4 1.387(3) . ?
C5 C6 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.503(4) . ?
C6 C1 1.381(4) . ?
C4 C3 1.381(4) . ?
C4 H4 0.9300 . ?
C1 C2 1.364(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C11 S1 C16 104.02(12) . . ?
C9 N1 H1A 120.0 . . ?
C9 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 C15 120.5(2) . . ?
C9 C8 C15 118.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 S1 120.39(18) . . ?
C10 C11 S1 118.65(17) . . ?
N1 C9 C8 119.3(2) . . ?
N1 C9 C10 121.8(2) . . ?
C8 C9 C10 118.9(2) . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 C13 123.1(2) . . ?
C9 C10 C13 118.7(2) . . ?
C12 C7 C8 119.0(2) . . ?
C12 C7 C5 119.2(2) . . ?
C8 C7 C5 121.6(2) . . ?
C4 C5 C6 116.9(2) . . ?
C4 C5 C7 118.9(2) . . ?
C6 C5 C7 124.2(2) . . ?
C7 C12 C11 121.2(2) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
O1 C13 C10 121.0(2) . . ?
O1 C13 C14 117.7(2) . . ?
C10 C13 C14 120.7(2) . . ?
C1 C6 C5 121.2(3) . . ?
C1 C6 Cl 118.2(2) . . ?
C5 C6 Cl 120.5(2) . . ?
N2 C15 C8 177.9(3) . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C16 S1 C11 C12 14.8(2) . . . . ?
C16 S1 C11 C10 -169.9(2) . . . . ?
C7 C8 C9 N1 -178.5(2) . . . . ?
C15 C8 C9 N1 -1.2(3) . . . . ?
C7 C8 C9 C10 3.8(3) . . . . ?
C15 C8 C9 C10 -178.9(2) . . . . ?
C12 C11 C10 C9 7.7(3) . . . . ?
S1 C11 C10 C9 -167.58(17) . . . . ?
C12 C11 C10 C13 -169.6(2) . . . . ?
S1 C11 C10 C13 15.1(3) . . . . ?
N1 C9 C10 C11 173.4(2) . . . . ?
C8 C9 C10 C11 -9.0(3) . . . . ?
N1 C9 C10 C13 -9.1(3) . . . . ?
C8 C9 C10 C13 168.5(2) . . . . ?
C9 C8 C7 C12 2.9(3) . . . . ?
C15 C8 C7 C12 -174.3(2) . . . . ?
C9 C8 C7 C5 178.0(2) . . . . ?
C15 C8 C7 C5 0.8(4) . . . . ?
C12 C7 C5 C4 55.4(3) . . . . ?
C8 C7 C5 C4 -119.7(3) . . . . ?
C12 C7 C5 C6 -122.8(3) . . . . ?
C8 C7 C5 C6 62.1(3) . . . . ?
C8 C7 C12 C11 -4.3(4) . . . . ?
C5 C7 C12 C11 -179.6(2) . . . . ?
C10 C11 C12 C7 -1.0(4) . . . . ?
S1 C11 C12 C7 174.18(19) . . . . ?
C11 C10 C13 O1 -150.4(2) . . . . ?
C9 C10 C13 O1 32.3(3) . . . . ?
C11 C10 C13 C14 38.8(4) . . . . ?
C9 C10 C13 C14 -138.5(3) . . . . ?
C4 C5 C6 C1 4.7(4) . . . . ?
C7 C5 C6 C1 -177.0(2) . . . . ?
C4 C5 C6 Cl -172.50(19) . . . . ?
C7 C5 C6 Cl 5.7(4) . . . . ?
C6 C5 C4 C3 -2.9(4) . . . . ?
C7 C5 C4 C3 178.8(3) . . . . ?
C5 C6 C1 C2 -3.0(4) . . . . ?
Cl C6 C1 C2 174.3(2) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 2.7(5) . . . . ?
C5 C4 C3 C2 -0.8(4) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_dhs40_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1974747'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap' 'University of Delhi'
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O3 S2'
_chemical_formula_sum            'C16 H20 O3 S2'
_chemical_formula_weight         324.44

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'
Cl Cl 0.1484 0.1585 '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      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                   7.4509(5)
_cell_length_b                   8.5535(6)
_cell_length_c                   13.4726(9)
_cell_angle_alpha                87.055(2)
_cell_angle_beta                 83.603(2)
_cell_angle_gamma                79.582(2)
_cell_volume                     838.78(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    7996
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.897
_exptl_transmission_factor_max   0.962
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11608
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.422
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4093
_reflns_number_gt                3634
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0489P)²+0.3110P] 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         4093
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
S2 S 0.46545(9) 0.13008(6) 0.10169(4) 0.05031(17) Uani 1 1 d . . . . .
S1 S 0.74814(7) 0.33188(6) 0.13900(4) 0.05150(17) Uani 1 1 d . . . . .
O1 O 0.37145(18) 0.51498(14) 0.18648(9) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.2278(2) -0.11415(16) 0.61504(10) 0.0462(3) Uani 1 1 d . . . . .
O3 O 0.2727(2) 0.15546(18) 0.67416(9) 0.0501(4) Uani 1 1 d . . . . .
C10 C 0.2496(2) -0.0021(2) 0.54112(13) 0.0345(3) Uani 1 1 d . . . . .
C2 C 0.4076(2) 0.37226(19) 0.23842(12) 0.0339(3) Uani 1 1 d . . . . .
C12 C 0.2874(2) 0.2702(2) 0.50425(12) 0.0337(3) Uani 1 1 d . . . . .
H008 H 0.2977 0.3694 0.5259 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3020(2) 0.37834(19) 0.32764(12) 0.0331(3) Uani 1 1 d . . . . .
C1 C 0.5491(3) 0.2465(2) 0.19053(12) 0.0363(4) Uani 1 1 d . . . . .
H00A H 0.5904 0.1719 0.2444 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2700(2) 0.1468(2) 0.57343(12) 0.0345(3) Uani 1 1 d . . . . .
C4 C 0.1947(3) 0.5360(2) 0.33115(14) 0.0397(4) Uani 1 1 d . . . . .
H00C H 0.1102 0.5772 0.3835 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2724(3) 0.0988(2) 0.37121(13) 0.0395(4) Uani 1 1 d . . . . .
H00D H 0.2747 0.0815 0.3035 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2894(2) 0.24667(19) 0.40154(12) 0.0323(3) Uani 1 1 d . . . . .
C9 C 0.2519(3) -0.0249(2) 0.44044(13) 0.0398(4) Uani 1 1 d . . . . .
H00F H 0.2397 -0.1235 0.4186 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2391(3) 0.6129(2) 0.24473(14) 0.0408(4) Uani 1 1 d . . . . .
C13 C 0.2070(3) -0.2663(2) 0.58461(17) 0.0516(5) Uani 1 1 d . . . . .
H00B H 0.1033 -0.2547 0.5468 0.077 Uiso 1 1 calc R U . . .
H00E H 0.1879 -0.3338 0.6426 0.077 Uiso 1 1 calc R U . . .
H00G H 0.3157 -0.3129 0.5440 0.077 Uiso 1 1 calc R U . . .
C6 C 0.1742(4) 0.7727(2) 0.20077(19) 0.0608(6) Uani 1 1 d . . . . .
H00H H 0.2751 0.8291 0.1881 0.091 Uiso 1 1 calc R U . . .
H00I H 0.0808 0.8307 0.2466 0.091 Uiso 1 1 calc R U . . .
H00J H 0.1246 0.7619 0.1392 0.091 Uiso 1 1 calc R U . . .
C14 C 0.3118(4) 0.2963(3) 0.71061(16) 0.0616(6) Uani 1 1 d . . . . .
H00K H 0.4265 0.3172 0.6777 0.092 Uiso 1 1 calc R U . . .
H00L H 0.3195 0.2837 0.7813 0.092 Uiso 1 1 calc R U . . .
H00M H 0.2158 0.3836 0.6975 0.092 Uiso 1 1 calc R U . . .
C15 C 0.3876(4) 0.2778(3) 0.01013(17) 0.0661(7) Uani 1 1 d . . . . .
H00N H 0.3480 0.2278 -0.0438 0.099 Uiso 1 1 calc R U . . .
H00O H 0.4859 0.3322 -0.0152 0.099 Uiso 1 1 calc R U . . .
H00P H 0.2869 0.3527 0.0401 0.099 Uiso 1 1 calc R U . . .
C16 C 0.9132(4) 0.1508(4) 0.1260(3) 0.0898(10) Uani 1 1 d . . . . .
H00Q H 0.8832 0.0894 0.0745 0.135 Uiso 1 1 calc R U . . .
H00R H 0.9111 0.0906 0.1881 0.135 Uiso 1 1 calc R U . . .
H00S H 1.0335 0.1759 0.1085 0.135 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
S2 C15 1.786(3) . ?
S2 C1 1.8233(19) . ?
S1 C16 1.798(3) . ?
S1 C1 1.8237(19) . ?
O1 C5 1.373(2) . ?
O1 C2 1.3739(19) . ?
O2 C10 1.364(2) . ?
O2 C13 1.424(2) . ?
O3 C11 1.365(2) . ?
O3 C14 1.413(2) . ?
C10 C9 1.378(2) . ?
C10 C11 1.406(2) . ?
C2 C3 1.359(2) . ?
C2 C1 1.481(2) . ?
C12 C11 1.386(2) . ?
C12 C7 1.407(2) . ?
C12 H008 0.9300 . ?
C3 C4 1.438(2) . ?
C3 C7 1.473(2) . ?
C1 H00A 0.9800 . ?
C4 C5 1.346(3) . ?
C4 H00C 0.9300 . ?
C8 C7 1.381(2) . ?
C8 C9 1.392(2) . ?
C8 H00D 0.9300 . ?
C9 H00F 0.9300 . ?
C5 C6 1.482(3) . ?
C13 H00B 0.9600 . ?
C13 H00E 0.9600 . ?
C13 H00G 0.9600 . ?
C6 H00H 0.9600 . ?
C6 H00I 0.9600 . ?
C6 H00J 0.9600 . ?
C14 H00K 0.9600 . ?
C14 H00L 0.9600 . ?
C14 H00M 0.9600 . ?
C15 H00N 0.9600 . ?
C15 H00O 0.9600 . ?
C15 H00P 0.9600 . ?
C16 H00Q 0.9600 . ?
C16 H00R 0.9600 . ?
C16 H00S 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
C15 S2 C1 102.25(10) . . ?
C16 S1 C1 98.53(12) . . ?
C5 O1 C2 107.03(13) . . ?
C10 O2 C13 116.73(15) . . ?
C11 O3 C14 117.84(15) . . ?
O2 C10 C9 125.09(16) . . ?
O2 C10 C11 115.42(15) . . ?
C9 C10 C11 119.49(15) . . ?
C3 C2 O1 110.14(14) . . ?
C3 C2 C1 132.81(15) . . ?
O1 C2 C1 117.04(14) . . ?
C11 C12 C7 120.53(15) . . ?
C11 C12 H008 119.7 . . ?
C7 C12 H008 119.7 . . ?
C2 C3 C4 105.69(15) . . ?
C2 C3 C7 126.98(15) . . ?
C4 C3 C7 127.16(15) . . ?
C2 C1 S2 114.53(13) . . ?
C2 C1 S1 109.50(12) . . ?
S2 C1 S1 113.56(9) . . ?
C2 C1 H00A 106.2 . . ?
S2 C1 H00A 106.2 . . ?
S1 C1 H00A 106.2 . . ?
O3 C11 C12 125.19(15) . . ?
O3 C11 C10 114.95(15) . . ?
C12 C11 C10 119.86(15) . . ?
C5 C4 C3 107.42(15) . . ?
C5 C4 H00C 126.3 . . ?
C3 C4 H00C 126.3 . . ?
C7 C8 C9 121.05(16) . . ?
C7 C8 H00D 119.5 . . ?
C9 C8 H00D 119.5 . . ?
C8 C7 C12 118.70(15) . . ?
C8 C7 C3 120.30(15) . . ?
C12 C7 C3 120.96(15) . . ?
C10 C9 C8 120.36(16) . . ?
C10 C9 H00F 119.8 . . ?
C8 C9 H00F 119.8 . . ?
C4 C5 O1 109.70(15) . . ?
C4 C5 C6 134.27(18) . . ?
O1 C5 C6 116.01(17) . . ?
O2 C13 H00B 109.5 . . ?
O2 C13 H00E 109.5 . . ?
H00B C13 H00E 109.5 . . ?
O2 C13 H00G 109.5 . . ?
H00B C13 H00G 109.5 . . ?
H00E C13 H00G 109.5 . . ?
C5 C6 H00H 109.5 . . ?
C5 C6 H00I 109.5 . . ?
H00H C6 H00I 109.5 . . ?
C5 C6 H00J 109.5 . . ?
H00H C6 H00J 109.5 . . ?
H00I C6 H00J 109.5 . . ?
O3 C14 H00K 109.5 . . ?
O3 C14 H00L 109.5 . . ?
H00K C14 H00L 109.5 . . ?
O3 C14 H00M 109.5 . . ?
H00K C14 H00M 109.5 . . ?
H00L C14 H00M 109.5 . . ?
S2 C15 H00N 109.5 . . ?
S2 C15 H00O 109.5 . . ?
H00N C15 H00O 109.5 . . ?
S2 C15 H00P 109.5 . . ?
H00N C15 H00P 109.5 . . ?
H00O C15 H00P 109.5 . . ?
S1 C16 H00Q 109.5 . . ?
S1 C16 H00R 109.5 . . ?
H00Q C16 H00R 109.5 . . ?
S1 C16 H00S 109.5 . . ?
H00Q C16 H00S 109.5 . . ?
H00R C16 H00S 109.5 . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.048

