# 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_cxy1479_0m
_audit_block_doi                 10.5517/ccdc.csd.cc29kdmx
_database_code_depnum_ccdc_archive 'CCDC 2131889'
loop_
_audit_author_name
_audit_author_address
'Shengqing Ye'
;Taizhou University
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O4 S'
_chemical_formula_sum            'C16 H18 O4 S'
_chemical_formula_weight         306.36
_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 0.0033 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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1786(3)
_cell_length_b                   18.5224(7)
_cell_length_c                   9.2041(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.6160(10)
_cell_angle_gamma                90
_cell_volume                     1491.41(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0929 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.9348.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21765
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3062
_reflns_number_total             3708
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0085(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.8921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C14(H14A,H14B,H14C)
;
_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 0.76326(4) 0.25248(2) 0.11121(4) 0.01272(10) Uani 1 1 d . . . . .
O1 O 0.78796(12) 0.16911(5) 0.14143(12) 0.0184(2) Uani 1 1 d . . . . .
O2 O 0.77572(11) 0.41047(5) 0.21646(11) 0.0151(2) Uani 1 1 d . . . . .
O3 O 0.89011(12) 0.28136(6) 0.07058(12) 0.0191(2) Uani 1 1 d . . . . .
O4 O 0.61301(12) 0.25828(6) 0.00669(12) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.78433(17) 0.44017(8) 0.75924(17) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.799456 0.457828 0.859644 0.024 Uiso 1 1 calc R U . . .
C2 C 0.83236(17) 0.37153(8) 0.73689(16) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.880288 0.341907 0.822230 0.023 Uiso 1 1 calc R U . . .
C3 C 0.81084(16) 0.34545(8) 0.58947(16) 0.0152(3) Uani 1 1 d . . . . .
H3 H 0.845928 0.298501 0.575243 0.018 Uiso 1 1 calc R U . . .
C4 C 0.73865(15) 0.38756(7) 0.46377(15) 0.0122(3) Uani 1 1 d . . . . .
C5 C 0.70710(15) 0.36246(7) 0.29782(14) 0.0109(3) Uani 1 1 d . . . . .
C6 C 0.53459(15) 0.36591(7) 0.21839(15) 0.0111(3) Uani 1 1 d . . . . .
C7 C 0.47266(16) 0.40825(7) 0.08979(16) 0.0149(3) Uani 1 1 d . . . . .
H7 H 0.538152 0.435963 0.048992 0.018 Uiso 1 1 calc R U . . .
C8 C 0.31534(17) 0.41031(8) 0.02044(17) 0.0191(3) Uani 1 1 d . . . . .
H8 H 0.274112 0.439391 -0.067457 0.023 Uiso 1 1 calc R U . . .
C9 C 0.21842(16) 0.37021(8) 0.07877(17) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.111111 0.371475 0.030758 0.023 Uiso 1 1 calc R U . . .
C10 C 0.94458(17) 0.14224(8) 0.19787(17) 0.0208(3) Uani 1 1 d . . . . .
H10A H 0.990740 0.142343 0.114780 0.031 Uiso 1 1 calc R U . . .
H10B H 0.943943 0.092907 0.236141 0.031 Uiso 1 1 calc R U . . .
H10C H 1.004183 0.173440 0.280553 0.031 Uiso 1 1 calc R U . . .
C11 C 0.76712(15) 0.28438(7) 0.29435(14) 0.0115(3) Uani 1 1 d . . . . .
H11A H 0.705111 0.251409 0.336413 0.014 Uiso 1 1 calc R U . . .
H11B H 0.873713 0.282024 0.362334 0.014 Uiso 1 1 calc R U . . .
C12 C 0.43586(15) 0.32602(7) 0.27733(16) 0.0133(3) Uani 1 1 d . . . . .
H12 H 0.476551 0.297217 0.365746 0.016 Uiso 1 1 calc R U . . .
C13 C 0.27913(16) 0.32819(8) 0.20777(17) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.213137 0.300821 0.248557 0.020 Uiso 1 1 calc R U . . .
C14 C 0.93496(16) 0.42453(8) 0.28515(18) 0.0203(3) Uani 1 1 d . . . . .
H14A H 0.949966 0.450074 0.381822 0.030 Uiso 1 1 calc R U . . .
H14B H 0.972962 0.454392 0.216489 0.030 Uiso 1 1 calc R U . . .
H14C H 0.991094 0.378754 0.304212 0.030 Uiso 1 1 calc R U . . .
C15 C 0.71382(17) 0.48325(8) 0.63425(18) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.681557 0.530693 0.648965 0.024 Uiso 1 1 calc R U . . .
C16 C 0.69060(16) 0.45696(8) 0.48808(17) 0.0171(3) Uani 1 1 d . . . . .
H16 H 0.641289 0.486517 0.403057 0.020 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 1.5732(10) . ?
S1 O3 1.4301(10) . ?
S1 O4 1.4269(10) . ?
S1 C11 1.7764(13) . ?
O1 C10 1.4602(17) . ?
O2 C5 1.4261(15) . ?
O2 C14 1.4299(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(2) . ?
C1 C15 1.389(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3864(19) . ?
C4 C5 1.5379(18) . ?
C4 C16 1.3989(19) . ?
C5 C6 1.5314(18) . ?
C5 C11 1.5514(18) . ?
C6 C7 1.3899(19) . ?
C6 C12 1.3996(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(2) . ?
C9 H9 0.9500 . ?
C9 C13 1.388(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.3869(19) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
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 C11 101.44(6) . . ?
O3 S1 O1 109.16(6) . . ?
O3 S1 C11 109.86(6) . . ?
O4 S1 O1 104.55(6) . . ?
O4 S1 O3 119.52(7) . . ?
O4 S1 C11 110.63(6) . . ?
C10 O1 S1 118.11(9) . . ?
C5 O2 C14 115.86(10) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C15 119.68(13) . . ?
C15 C1 H1 120.2 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.36(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.49(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 123.88(12) . . ?
C3 C4 C16 118.54(13) . . ?
C16 C4 C5 117.58(12) . . ?
O2 C5 C4 110.65(10) . . ?
O2 C5 C6 106.29(10) . . ?
O2 C5 C11 110.76(10) . . ?
C4 C5 C11 109.93(10) . . ?
C6 C5 C4 108.56(10) . . ?
C6 C5 C11 110.57(10) . . ?
C7 C6 C5 121.83(12) . . ?
C7 C6 C12 118.82(12) . . ?
C12 C6 C5 119.35(12) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.42(13) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.42(13) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C13 119.57(13) . . ?
C13 C9 H9 120.2 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 108.5 . . ?
S1 C11 H11B 108.5 . . ?
C5 C11 S1 115.11(9) . . ?
C5 C11 H11A 108.5 . . ?
C5 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C6 C12 H12 119.7 . . ?
C13 C12 C6 120.57(13) . . ?
C13 C12 H12 119.7 . . ?
C9 C13 H13 119.9 . . ?
C12 C13 C9 120.20(13) . . ?
C12 C13 H13 119.9 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 H15 120.0 . . ?
C16 C15 C1 119.92(14) . . ?
C16 C15 H15 120.0 . . ?
C4 C16 H16 119.5 . . ?
C15 C16 C4 121.00(13) . . ?
C15 C16 H16 119.5 . . ?

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 C11 C5 -165.77(9) . . . . ?
O2 C5 C6 C7 1.79(16) . . . . ?
O2 C5 C6 C12 -177.54(11) . . . . ?
O2 C5 C11 S1 -48.94(13) . . . . ?
O3 S1 O1 C10 29.40(12) . . . . ?
O3 S1 C11 C5 78.81(11) . . . . ?
O4 S1 O1 C10 158.38(10) . . . . ?
O4 S1 C11 C5 -55.28(11) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C1 C15 C16 C4 -0.7(2) . . . . ?
C2 C1 C15 C16 0.7(2) . . . . ?
C2 C3 C4 C5 -178.57(13) . . . . ?
C2 C3 C4 C16 1.1(2) . . . . ?
C3 C4 C5 O2 -122.46(13) . . . . ?
C3 C4 C5 C6 121.27(14) . . . . ?
C3 C4 C5 C11 0.20(17) . . . . ?
C3 C4 C16 C15 -0.2(2) . . . . ?
C4 C5 C6 C7 120.84(13) . . . . ?
C4 C5 C6 C12 -58.49(15) . . . . ?
C4 C5 C11 S1 -171.53(9) . . . . ?
C5 C4 C16 C15 179.50(13) . . . . ?
C5 C6 C7 C8 -179.88(12) . . . . ?
C5 C6 C12 C13 179.95(12) . . . . ?
C6 C5 C11 S1 68.62(12) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C6 C12 C13 C9 -0.1(2) . . . . ?
C7 C6 C12 C13 0.6(2) . . . . ?
C7 C8 C9 C13 0.4(2) . . . . ?
C8 C9 C13 C12 -0.4(2) . . . . ?
C11 S1 O1 C10 -86.53(11) . . . . ?
C11 C5 C6 C7 -118.49(13) . . . . ?
C11 C5 C6 C12 62.19(15) . . . . ?
C12 C6 C7 C8 -0.6(2) . . . . ?
C14 O2 C5 C4 52.89(14) . . . . ?
C14 O2 C5 C6 170.56(11) . . . . ?
C14 O2 C5 C11 -69.28(14) . . . . ?
C15 C1 C2 C3 0.2(2) . . . . ?
C16 C4 C5 O2 57.83(15) . . . . ?
C16 C4 C5 C6 -58.44(15) . . . . ?
C16 C4 C5 C11 -179.51(12) . . . . ?

_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_1
_audit_block_doi                 10.5517/ccdc.csd.cc29kdq0
_database_code_depnum_ccdc_archive 'CCDC 2131892'
loop_
_audit_author_name
_audit_author_address
'Shengqing Ye'
;Taizhou University
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-09-29 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         ?
_chemical_formula_sum            'C14 H20 O4 S'
_chemical_formula_weight         284.36

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           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                   11.5469(15)
_cell_length_b                   8.3647(11)
_cell_length_c                   15.835(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.211(2)
_cell_angle_gamma                90
_cell_volume                     1475.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2784
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.04

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7236
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.666
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2589
_reflns_number_gt                2045
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0628P)²+0.3602P] 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         2589
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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 0.41774(5) 0.08965(6) 0.37386(3) 0.05036(19) Uani 1 1 d . . . . .
O4 O 0.38077(12) 0.16946(17) 0.28182(8) 0.0524(4) Uani 1 1 d . . . . .
O1 O 0.39155(11) 0.47149(17) 0.56178(9) 0.0522(4) Uani 1 1 d . . . . .
O3 O 0.54149(14) 0.0488(2) 0.39429(10) 0.0727(5) Uani 1 1 d . . . . .
O2 O 0.33241(18) -0.03342(19) 0.36967(12) 0.0845(6) Uani 1 1 d . . . . .
C5 C 0.27735(14) 0.3038(2) 0.44648(10) 0.0371(4) Uani 1 1 d . . . . .
C4 C 0.29388(15) 0.4402(2) 0.51438(11) 0.0389(4) Uani 1 1 d . . . . .
C6 C 0.21556(15) 0.3744(2) 0.35685(11) 0.0383(4) Uani 1 1 d . . . . .
C13 C 0.40340(15) 0.2413(2) 0.44861(11) 0.0404(4) Uani 1 1 d . . . . .
H13A H 0.4394 0.2017 0.5072 0.049 Uiso 1 1 calc R U . . .
H13B H 0.4511 0.3319 0.4394 0.049 Uiso 1 1 calc R U . . .
C3 C 0.18320(16) 0.5312(2) 0.52261(13) 0.0496(5) Uani 1 1 d . . . . .
H3 H 0.1129 0.4910 0.4786 0.060 Uiso 1 1 calc R U . . .
C11 C 0.11480(17) 0.3071(3) 0.30162(13) 0.0551(5) Uani 1 1 d . . . . .
H11 H 0.0802 0.2171 0.3194 0.066 Uiso 1 1 calc R U . . .
C12 C 0.20361(18) 0.1736(2) 0.47788(14) 0.0551(5) Uani 1 1 d . . . . .
H12A H 0.2459 0.1391 0.5355 0.083 Uiso 1 1 calc R U . . .
H12B H 0.1921 0.0844 0.4385 0.083 Uiso 1 1 calc R U . . .
H12C H 0.1270 0.2165 0.4792 0.083 Uiso 1 1 calc R U . . .
C7 C 0.26310(18) 0.5104(2) 0.32864(13) 0.0536(5) Uani 1 1 d . . . . .
H7 H 0.3302 0.5589 0.3653 0.064 Uiso 1 1 calc R U . . .
C1 C 0.1652(2) 0.5030(3) 0.61334(15) 0.0704(7) Uani 1 1 d . . . . .
H1A H 0.1536 0.3909 0.6213 0.106 Uiso 1 1 calc R U . . .
H1B H 0.0959 0.5610 0.6190 0.106 Uiso 1 1 calc R U . . .
H1C H 0.2347 0.5392 0.6569 0.106 Uiso 1 1 calc R U . . .
C10 C 0.0645(2) 0.3727(4) 0.21948(15) 0.0732(7) Uani 1 1 d . . . . .
H10 H -0.0035 0.3265 0.1828 0.088 Uiso 1 1 calc R U . . .
C8 C 0.2125(2) 0.5750(3) 0.24716(16) 0.0747(7) Uani 1 1 d . . . . .
H8 H 0.2452 0.6667 0.2294 0.090 Uiso 1 1 calc R U . . .
C14 C 0.4659(2) 0.2695(3) 0.25421(15) 0.0712(7) Uani 1 1 d . . . . .
H14A H 0.4252 0.3295 0.2034 0.107 Uiso 1 1 calc R U . . .
H14B H 0.5265 0.2038 0.2403 0.107 Uiso 1 1 calc R U . . .
H14C H 0.5028 0.3417 0.3006 0.107 Uiso 1 1 calc R U . . .
C9 C 0.1144(2) 0.5043(4) 0.19251(15) 0.0791(8) Uani 1 1 d . . . . .
H9 H 0.0817 0.5460 0.1369 0.095 Uiso 1 1 calc R U . . .
C2 C 0.1972(2) 0.7099(3) 0.50727(17) 0.0734(7) Uani 1 1 d . . . . .
H2A H 0.2648 0.7508 0.5510 0.110 Uiso 1 1 calc R U . . .
H2B H 0.1258 0.7652 0.5109 0.110 Uiso 1 1 calc R U . . .
H2C H 0.2097 0.7259 0.4503 0.110 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 1.4145(17) . ?
S1 O3 1.4215(16) . ?
S1 O4 1.5574(14) . ?
S1 C13 1.7722(18) . ?
O4 C14 1.443(3) . ?
O1 C4 1.208(2) . ?
C5 C6 1.530(2) . ?
C5 C13 1.539(2) . ?
C5 C4 1.545(2) . ?
C5 C12 1.543(2) . ?
C4 C3 1.523(2) . ?
C6 C11 1.379(3) . ?
C6 C7 1.387(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C3 C1 1.523(3) . ?
C3 C2 1.530(3) . ?
C3 H3 0.9800 . ?
C11 C10 1.391(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C10 C9 1.362(4) . ?
C10 H10 0.9300 . ?
C8 C9 1.367(4) . ?
C8 H8 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 H9 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
O2 S1 O3 118.80(11) . . ?
O2 S1 O4 104.57(10) . . ?
O3 S1 O4 109.17(9) . . ?
O2 S1 C13 111.49(9) . . ?
O3 S1 C13 106.54(9) . . ?
O4 S1 C13 105.52(8) . . ?
C14 O4 S1 119.38(13) . . ?
C6 C5 C13 111.08(14) . . ?
C6 C5 C4 107.65(14) . . ?
C13 C5 C4 106.99(13) . . ?
C6 C5 C12 114.14(14) . . ?
C13 C5 C12 110.62(15) . . ?
C4 C5 C12 105.94(14) . . ?
O1 C4 C3 120.39(16) . . ?
O1 C4 C5 121.16(16) . . ?
C3 C4 C5 118.42(14) . . ?
C11 C6 C7 118.03(18) . . ?
C11 C6 C5 122.77(17) . . ?
C7 C6 C5 119.19(16) . . ?
C5 C13 S1 118.83(12) . . ?
C5 C13 H13A 107.6 . . ?
S1 C13 H13A 107.6 . . ?
C5 C13 H13B 107.6 . . ?
S1 C13 H13B 107.6 . . ?
H13A C13 H13B 107.0 . . ?
C1 C3 C4 109.17(16) . . ?
C1 C3 C2 110.34(19) . . ?
C4 C3 C2 110.46(17) . . ?
C1 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
C6 C11 C10 120.5(2) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
O2 S1 O4 C14 -162.82(16) . . . . ?
O3 S1 O4 C14 -34.69(18) . . . . ?
C13 S1 O4 C14 79.47(16) . . . . ?
C6 C5 C4 O1 -125.00(18) . . . . ?
C13 C5 C4 O1 -5.5(2) . . . . ?
C12 C5 C4 O1 112.51(18) . . . . ?
C6 C5 C4 C3 57.07(19) . . . . ?
C13 C5 C4 C3 176.53(14) . . . . ?
C12 C5 C4 C3 -65.43(19) . . . . ?
C13 C5 C6 C11 113.78(19) . . . . ?
C4 C5 C6 C11 -129.39(18) . . . . ?
C12 C5 C6 C11 -12.1(2) . . . . ?
C13 C5 C6 C7 -65.2(2) . . . . ?
C4 C5 C6 C7 51.6(2) . . . . ?
C12 C5 C6 C7 168.91(17) . . . . ?
C6 C5 C13 S1 -59.56(18) . . . . ?
C4 C5 C13 S1 -176.79(11) . . . . ?
C12 C5 C13 S1 68.27(17) . . . . ?
O2 S1 C13 C5 -45.26(17) . . . . ?
O3 S1 C13 C5 -176.34(13) . . . . ?
O4 S1 C13 C5 67.68(14) . . . . ?
O1 C4 C3 C1 -62.0(2) . . . . ?
C5 C4 C3 C1 115.93(19) . . . . ?
O1 C4 C3 C2 59.5(2) . . . . ?
C5 C4 C3 C2 -122.57(18) . . . . ?
C7 C6 C11 C10 1.3(3) . . . . ?
C5 C6 C11 C10 -177.70(18) . . . . ?
C11 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 C7 C8 177.89(19) . . . . ?
C6 C11 C10 C9 0.1(3) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C11 C10 C9 C8 -1.7(4) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.039



