# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 2207903'
loop_
_audit_author_name
_audit_author_address
k-so-OMe
;snnu
China
;
_audit_update_record             
;
2022-09-17 deposited with the CCDC.	2022-12-02 downloaded from the CCDC.
;
_audit_creation_date             2022-06-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O3 S'
_chemical_formula_sum            'C16 H14 O3 S'
_chemical_formula_weight         286.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'

_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.
;
_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'
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                   7.6531(5)
_cell_length_b                   10.1518(7)
_cell_length_c                   18.1461(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1409.82(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9454
_cell_measurement_temperature    219.00
_cell_measurement_theta_max      68.513
_cell_measurement_theta_min      4.992
_shelx_estimated_absorpt_T_max   0.574
_shelx_estimated_absorpt_T_min   0.423
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1247 before and 0.0763 after correction.
The Ratio of minimum to maximum transmission is 0.8250.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26001
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.507
_diffrn_reflns_theta_min         4.874
_diffrn_ambient_temperature      219.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2520
_reflns_number_total             2592
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.2729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0617
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C2(H2), C5(H5), C11(H11), C3(H3), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C)
2.c :
 C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.82348(6) 0.53726(5) 0.35306(3) 0.01865(13) Uani 1 1 d . . . . .
O1 O 0.4855(2) 0.57153(16) 0.43343(9) 0.0293(4) Uani 1 1 d . . . . .
O3 O 0.9099(2) 0.26432(14) 0.36356(8) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.8050(2) 0.67899(14) 0.37426(8) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.5994(3) 0.3989(2) 0.26375(12) 0.0217(4) Uani 1 1 d . . . . .
C4 C 0.7498(3) 0.3642(2) 0.22107(12) 0.0249(5) Uani 1 1 d . . . . .
C6 C 0.9220(3) 0.3178(2) 0.43191(11) 0.0201(4) Uani 1 1 d . . . . .
C8 C 0.8660(2) 0.4490(2) 0.43708(11) 0.0193(4) Uani 1 1 d . . . . .
C10 C 0.6121(3) 0.4744(2) 0.32869(11) 0.0187(4) Uani 1 1 d . . . . .
C12 C 0.4624(3) 0.50318(19) 0.36981(12) 0.0223(4) Uani 1 1 d . . . . .
C14 C 0.8703(3) 0.5153(2) 0.50336(11) 0.0232(5) Uani 1 1 d . . . . .
H14 H 0.832126 0.603124 0.506185 0.028 Uiso 1 1 calc R U . . .
C16 C 0.9860(3) 0.2547(2) 0.49434(12) 0.0254(5) Uani 1 1 d . . . . .
H16 H 1.025770 0.167192 0.491629 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3002(3) 0.4597(2) 0.34468(12) 0.0285(5) Uani 1 1 d . . . . .
H2 H 0.198476 0.480316 0.371316 0.034 Uiso 1 1 calc R U . . .
C9 C 0.8651(3) 0.3257(2) 0.18239(13) 0.0318(5) Uani 1 1 d . . . . .
H9 H 0.955942 0.295388 0.151919 0.038 Uiso 1 1 calc R U . . .
C5 C 0.9903(3) 0.3227(2) 0.56079(12) 0.0276(5) Uani 1 1 d . . . . .
H5 H 1.034012 0.280537 0.603062 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2886(3) 0.3865(3) 0.28087(13) 0.0329(5) Uani 1 1 d . . . . .
H11 H 0.178442 0.358012 0.264439 0.039 Uiso 1 1 calc R U . . .
C3 C 0.9313(3) 0.4513(2) 0.56595(12) 0.0275(5) Uani 1 1 d . . . . .
H3 H 0.932659 0.495126 0.611578 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4355(3) 0.3541(2) 0.24064(12) 0.0286(5) Uani 1 1 d . . . . .
H13 H 0.425465 0.302263 0.197931 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9734(4) 0.1333(2) 0.35226(14) 0.0361(5) Uani 1 1 d . . . . .
H7A H 0.960427 0.109646 0.300764 0.054 Uiso 1 1 calc R U . . .
H7B H 0.907021 0.072421 0.382488 0.054 Uiso 1 1 calc R U . . .
H7C H 1.095833 0.129033 0.365887 0.054 Uiso 1 1 calc R U . . .
C15 C 0.3366(4) 0.6017(3) 0.47671(14) 0.0379(6) Uani 1 1 d . . . . .
H15A H 0.257100 0.656177 0.448319 0.057 Uiso 1 1 calc R U . . .
H15B H 0.372629 0.648922 0.520633 0.057 Uiso 1 1 calc R U . . .
H15C H 0.278132 0.520770 0.490776 0.057 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 O2 1.4961(15) . ?
S1 C8 1.798(2) . ?
S1 C10 1.794(2) . ?
O1 C12 1.359(3) . ?
O1 C15 1.418(3) . ?
O3 C6 1.357(2) . ?
O3 C7 1.431(3) . ?
C1 C4 1.431(3) . ?
C1 C10 1.409(3) . ?
C1 C13 1.399(3) . ?
C4 C9 1.193(3) . ?
C6 C8 1.402(3) . ?
C6 C16 1.391(3) . ?
C8 C14 1.378(3) . ?
C10 C12 1.398(3) . ?
C12 C2 1.394(3) . ?
C14 H14 0.9400 . ?
C14 C3 1.389(3) . ?
C16 H16 0.9400 . ?
C16 C5 1.390(3) . ?
C2 H2 0.9400 . ?
C2 C11 1.379(3) . ?
C9 H9 0.9400 . ?
C5 H5 0.9400 . ?
C5 C3 1.384(3) . ?
C11 H11 0.9400 . ?
C11 C13 1.380(3) . ?
C3 H3 0.9400 . ?
C13 H13 0.9400 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

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
O2 S1 C8 106.16(9) . . ?
O2 S1 C10 108.66(9) . . ?
C10 S1 C8 101.24(9) . . ?
C12 O1 C15 118.44(19) . . ?
C6 O3 C7 118.66(17) . . ?
C10 C1 C4 122.1(2) . . ?
C13 C1 C4 118.6(2) . . ?
C13 C1 C10 119.29(19) . . ?
C9 C4 C1 173.5(3) . . ?
O3 C6 C8 114.84(18) . . ?
O3 C6 C16 125.73(18) . . ?
C16 C6 C8 119.42(19) . . ?
C6 C8 S1 118.16(16) . . ?
C14 C8 S1 120.06(16) . . ?
C14 C8 C6 120.96(18) . . ?
C1 C10 S1 117.48(15) . . ?
C12 C10 S1 122.22(15) . . ?
C12 C10 C1 120.24(18) . . ?
O1 C12 C10 116.95(18) . . ?
O1 C12 C2 123.77(19) . . ?
C2 C12 C10 119.27(19) . . ?
C8 C14 H14 120.2 . . ?
C8 C14 C3 119.6(2) . . ?
C3 C14 H14 120.2 . . ?
C6 C16 H16 120.5 . . ?
C5 C16 C6 119.1(2) . . ?
C5 C16 H16 120.5 . . ?
C12 C2 H2 119.9 . . ?
C11 C2 C12 120.17(19) . . ?
C11 C2 H2 119.9 . . ?
C4 C9 H9 180.0 . . ?
C16 C5 H5 119.3 . . ?
C3 C5 C16 121.3(2) . . ?
C3 C5 H5 119.3 . . ?
C2 C11 H11 119.3 . . ?
C2 C11 C13 121.3(2) . . ?
C13 C11 H11 119.3 . . ?
C14 C3 H3 120.2 . . ?
C5 C3 C14 119.7(2) . . ?
C5 C3 H3 120.2 . . ?
C1 C13 H13 120.2 . . ?
C11 C13 C1 119.6(2) . . ?
C11 C13 H13 120.2 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
S1 C8 C14 C3 -169.34(16) . . . . ?
S1 C10 C12 O1 -5.8(3) . . . . ?
S1 C10 C12 C2 175.06(16) . . . . ?
O1 C12 C2 C11 -177.5(2) . . . . ?
O3 C6 C8 S1 -10.7(2) . . . . ?
O3 C6 C8 C14 179.64(17) . . . . ?
O3 C6 C16 C5 180.00(19) . . . . ?
O2 S1 C8 C6 -167.95(15) . . . . ?
O2 S1 C8 C14 1.81(18) . . . . ?
O2 S1 C10 C1 134.01(16) . . . . ?
O2 S1 C10 C12 -43.00(19) . . . . ?
C1 C10 C12 O1 177.23(18) . . . . ?
C1 C10 C12 C2 -1.9(3) . . . . ?
C4 C1 C10 S1 4.6(3) . . . . ?
C4 C1 C10 C12 -178.28(19) . . . . ?
C4 C1 C13 C11 -179.9(2) . . . . ?
C6 C8 C14 C3 0.1(3) . . . . ?
C6 C16 C5 C3 0.4(3) . . . . ?
C8 S1 C10 C1 -114.48(16) . . . . ?
C8 S1 C10 C12 68.51(18) . . . . ?
C8 C6 C16 C5 1.0(3) . . . . ?
C8 C14 C3 C5 1.2(3) . . . . ?
C10 S1 C8 C6 78.65(16) . . . . ?
C10 S1 C8 C14 -111.59(17) . . . . ?
C10 C1 C13 C11 1.2(3) . . . . ?
C10 C12 C2 C11 1.5(3) . . . . ?
C12 C2 C11 C13 0.2(4) . . . . ?
C16 C6 C8 S1 168.41(16) . . . . ?
C16 C6 C8 C14 -1.2(3) . . . . ?
C16 C5 C3 C14 -1.5(3) . . . . ?
C2 C11 C13 C1 -1.6(4) . . . . ?
C13 C1 C10 S1 -176.56(16) . . . . ?
C13 C1 C10 C12 0.5(3) . . . . ?
C7 O3 C6 C8 176.50(19) . . . . ?
C7 O3 C6 C16 -2.5(3) . . . . ?
C15 O1 C12 C10 -179.65(19) . . . . ?
C15 O1 C12 C2 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_d8v22234_0m
_database_code_depnum_ccdc_archive 'CCDC 2207905'
loop_
_audit_author_name
_audit_author_address
k-MeOMe
;snnu
China
;
_audit_update_record             
;
2022-09-17 deposited with the CCDC.	2022-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O2 S'
_chemical_formula_weight         270.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           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                   7.6856(3)
_cell_length_b                   10.0965(4)
_cell_length_c                   18.0404(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1399.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5370
_cell_measurement_theta_min      5.762
_cell_measurement_theta_max      54.888

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            6756
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.881
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2740
_reflns_number_gt                2638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.988

_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-2013 (Sheldrick, 2013)'
_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)+(0.0379P)²+0.2155P] 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     SHELXL
_refine_ls_extinction_coef       0.025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2740
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.17155(8) 0.45849(6) 0.35028(3) 0.02946(19) Uani 1 1 d . . . . .
O1 O 0.1848(3) 0.31507(17) 0.37065(12) 0.0443(5) Uani 1 1 d . . . . .
O2 O 0.1078(3) 0.73747(17) 0.36669(10) 0.0397(5) Uani 1 1 d . . . . .
C1 C 0.3877(3) 0.5181(2) 0.33134(14) 0.0293(5) Uani 1 1 d . . . . .
C2 C 0.5326(3) 0.4805(3) 0.37388(16) 0.0377(6) Uani 1 1 d . . . . .
C3 C 0.6938(4) 0.5278(3) 0.35136(19) 0.0498(8) Uani 1 1 d . . . . .
H3 H 0.7930 0.5043 0.3789 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7134(4) 0.6076(4) 0.2903(2) 0.0542(9) Uani 1 1 d . . . . .
H4 H 0.8246 0.6379 0.2768 0.065 Uiso 1 1 calc R U . . .
C5 C 0.5709(4) 0.6432(3) 0.24894(17) 0.0448(7) Uani 1 1 d . . . . .
H5 H 0.5850 0.6980 0.2072 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4056(3) 0.5986(3) 0.26845(15) 0.0334(6) Uani 1 1 d . . . . .
C7 C 0.2599(4) 0.6363(3) 0.22291(16) 0.0376(6) Uani 1 1 d . . . . .
C8 C 0.1498(5) 0.6716(3) 0.18416(19) 0.0514(8) Uani 1 1 d . . . . .
H8 H 0.0601 0.7004 0.1526 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5229(5) 0.3926(3) 0.4420(2) 0.0544(8) Uani 1 1 d . . . . .
H9A H 0.4424 0.4307 0.4775 0.082 Uiso 1 1 calc R U . . .
H9B H 0.6374 0.3856 0.4642 0.082 Uiso 1 1 calc R U . . .
H9C H 0.4826 0.3051 0.4277 0.082 Uiso 1 1 calc R U . . .
C10 C 0.1238(3) 0.5439(3) 0.43527(14) 0.0291(5) Uani 1 1 d . . . . .
C11 C 0.1006(4) 0.4723(3) 0.49976(16) 0.0422(7) Uani 1 1 d . . . . .
H11 H 0.1236 0.3809 0.5005 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0435(5) 0.5356(4) 0.56322(17) 0.0526(8) Uani 1 1 d . . . . .
H12 H 0.0292 0.4874 0.6074 0.063 Uiso 1 1 calc R U . . .
C13 C 0.0077(5) 0.6687(3) 0.56175(17) 0.0507(8) Uani 1 1 d . . . . .
H13 H -0.0307 0.7112 0.6051 0.061 Uiso 1 1 calc R U . . .
C14 C 0.0276(4) 0.7412(3) 0.49701(17) 0.0424(7) Uani 1 1 d . . . . .
H14 H 0.0021 0.8323 0.4964 0.051 Uiso 1 1 calc R U . . .
C15 C 0.0851(3) 0.6788(2) 0.43337(14) 0.0310(6) Uani 1 1 d . . . . .
C16 C 0.0524(6) 0.8714(3) 0.3578(2) 0.0601(9) Uani 1 1 d . . . . .
H16A H 0.0708 0.8988 0.3069 0.090 Uiso 1 1 calc R U . . .
H16B H 0.1190 0.9282 0.3906 0.090 Uiso 1 1 calc R U . . .
H16C H -0.0703 0.8784 0.3698 0.090 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 1.4974(19) . ?
S1 C10 1.797(3) . ?
S1 C1 1.800(2) . ?
O2 C15 1.352(3) . ?
O2 C16 1.427(3) . ?
C1 C6 1.402(4) . ?
C1 C2 1.405(4) . ?
C2 C3 1.389(4) . ?
C2 C9 1.517(4) . ?
C3 C4 1.373(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.440(4) . ?
C7 C8 1.154(4) . ?
C8 H8 0.9400 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.381(4) . ?
C10 C15 1.394(3) . ?
C11 C12 1.383(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.372(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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 C10 105.57(12) . . ?
O1 S1 C1 107.89(11) . . ?
C10 S1 C1 100.96(11) . . ?
C15 O2 C16 118.5(2) . . ?
C6 C1 C2 121.4(2) . . ?
C6 C1 S1 115.97(19) . . ?
C2 C1 S1 122.5(2) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 C9 118.8(3) . . ?
C1 C2 C9 124.2(3) . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 118.7(3) . . ?
C1 C6 C7 122.6(2) . . ?
C8 C7 C6 175.9(3) . . ?
C7 C8 H8 180.0 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.3(2) . . ?
C11 C10 S1 119.6(2) . . ?
C15 C10 S1 119.42(19) . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O2 C15 C14 125.4(2) . . ?
O2 C15 C10 115.0(2) . . ?
C14 C15 C10 119.6(3) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 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 C6 136.23(19) . . . . ?
C10 S1 C1 C6 -113.29(19) . . . . ?
O1 S1 C1 C2 -40.0(2) . . . . ?
C10 S1 C1 C2 70.5(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
S1 C1 C2 C3 176.7(2) . . . . ?
C6 C1 C2 C9 -179.3(3) . . . . ?
S1 C1 C2 C9 -3.3(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C9 C2 C3 C4 179.9(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
S1 C1 C6 C5 -177.3(2) . . . . ?
C2 C1 C6 C7 178.6(3) . . . . ?
S1 C1 C6 C7 2.3(3) . . . . ?
O1 S1 C10 C11 -2.7(2) . . . . ?
C1 S1 C10 C11 -114.9(2) . . . . ?
O1 S1 C10 C15 -173.2(2) . . . . ?
C1 S1 C10 C15 74.5(2) . . . . ?
C15 C10 C11 C12 -1.8(4) . . . . ?
S1 C10 C11 C12 -172.3(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C16 O2 C15 C14 -6.7(4) . . . . ?
C16 O2 C15 C10 172.9(3) . . . . ?
C13 C14 C15 O2 179.1(3) . . . . ?
C13 C14 C15 C10 -0.5(4) . . . . ?
C11 C10 C15 O2 -178.1(2) . . . . ?
S1 C10 C15 O2 -7.6(3) . . . . ?
C11 C10 C15 C14 1.6(4) . . . . ?
S1 C10 C15 C14 172.1(2) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4

