# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1583233'
_audit_update_record             
;
2017-10-31 deposited with the CCDC.
2018-02-26 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         'C9 H12 O4 S2'
_chemical_formula_sum            'C9 H12 O4 S2'
_chemical_formula_weight         248.31

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'

_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                   7.5406(2)
_cell_length_b                   7.8875(3)
_cell_length_c                   8.9868(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.198(3)
_cell_angle_gamma                90
_cell_volume                     532.31(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6109
_cell_measurement_theta_min      5.6240
_cell_measurement_theta_max      72.9170

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.499
_shelx_estimated_absorpt_T_min   0.346
_shelx_estimated_absorpt_T_max   0.466
_exptl_absorpt_correction_T_min  0.66292
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.733
_oxdiff_exptl_absorpt_empirical_full_max 1.431
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            7772
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.941
_diffrn_reflns_theta_max         72.997
_diffrn_reflns_theta_full        1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.000
_reflns_number_total             2069
_reflns_number_gt                2061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.000

_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SHELXT 
G.M.Sheldrick,Acta Crystallogr.,Sect. A: Found.Crystallogr., 2008, 64,112-122.
;
_computing_structure_refinement  
;
 SHELXL-2016/6 (Sheldrick, 2016)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0433P)²+0.0840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2069
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.23705(7) 0.05248(7) 0.18151(6) 0.02317(15) Uani 1 1 d . . . . .
S2 S 0.08612(7) 0.38422(7) 0.13328(7) 0.02311(15) Uani 1 1 d . . . . .
O1 O 0.4378(2) 0.3112(2) 0.1542(2) 0.0233(4) Uani 1 1 d . . . . .
O2 O 0.7437(2) 0.6539(2) 0.23324(18) 0.0229(4) Uani 1 1 d . . . . .
O3 O 0.6087(2) 0.7414(2) 0.43615(18) 0.0220(4) Uani 1 1 d . . . . .
O4 O 0.3535(2) 0.6027(2) 0.33958(16) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.2718(3) 0.2562(3) 0.1561(2) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.4929(3) 0.4880(3) 0.1440(3) 0.0193(5) Uani 1 1 d . . . . .
H2 H 0.538293 0.512563 0.045056 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6376(3) 0.5150(3) 0.2718(3) 0.0199(5) Uani 1 1 d . . . . .
H3 H 0.708139 0.410475 0.299209 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7634(3) 0.7686(3) 0.3579(3) 0.0188(5) Uani 1 1 d . . . . .
C5 C 0.9291(3) 0.7257(4) 0.4583(3) 0.0272(5) Uani 1 1 d . . . . .
H5A H 0.936676 0.799576 0.546333 0.041 Uiso 1 1 calc R U . . .
H5B H 1.034351 0.742708 0.403564 0.041 Uiso 1 1 calc R U . . .
H5C H 0.923732 0.607110 0.490040 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7599(3) 0.9471(3) 0.2992(3) 0.0243(5) Uani 1 1 d . . . . .
H6A H 0.764465 1.026883 0.383105 0.037 Uiso 1 1 calc R U . . .
H6B H 0.649982 0.965309 0.234264 0.037 Uiso 1 1 calc R U . . .
H6C H 0.862852 0.965543 0.242081 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5327(3) 0.5830(3) 0.4000(2) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.542271 0.504808 0.487923 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3563(3) 0.6170(3) 0.1812(2) 0.0188(4) Uani 1 1 d . . . . .
H8 H 0.400260 0.732568 0.157269 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1725(3) 0.5935(3) 0.1034(2) 0.0214(5) Uani 1 1 d . . . . .
H9A H 0.176465 0.612549 -0.005076 0.026 Uiso 1 1 calc R U . . .
H9B H 0.091278 0.678865 0.141034 0.026 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 C1 1.647(2) . ?
S2 C1 1.724(2) . ?
S2 C9 1.803(3) . ?
O1 C1 1.326(3) . ?
O1 C2 1.461(3) . ?
O2 C3 1.417(3) . ?
O2 C4 1.437(3) . ?
O3 C7 1.400(3) . ?
O3 C4 1.431(3) . ?
O4 C7 1.418(3) . ?
O4 C8 1.430(3) . ?
C2 C8 1.506(3) . ?
C2 C3 1.526(3) . ?
C2 H2 1.0000 . ?
C3 C7 1.551(3) . ?
C3 H3 1.0000 . ?
C4 C6 1.503(4) . ?
C4 C5 1.512(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 1.0000 . ?
C8 C9 1.507(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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
C1 S2 C9 104.69(11) . . ?
C1 O1 C2 125.99(18) . . ?
C3 O2 C4 108.44(16) . . ?
C7 O3 C4 110.75(17) . . ?
C7 O4 C8 106.86(16) . . ?
O1 C1 S1 118.91(18) . . ?
O1 C1 S2 124.33(18) . . ?
S1 C1 S2 116.76(13) . . ?
O1 C2 C8 115.26(18) . . ?
O1 C2 C3 105.91(19) . . ?
C8 C2 C3 101.24(18) . . ?
O1 C2 H2 111.3 . . ?
C8 C2 H2 111.3 . . ?
C3 C2 H2 111.3 . . ?
O2 C3 C2 107.73(19) . . ?
O2 C3 C7 104.58(18) . . ?
C2 C3 C7 103.25(17) . . ?
O2 C3 H3 113.5 . . ?
C2 C3 H3 113.5 . . ?
C7 C3 H3 113.5 . . ?
O3 C4 O2 104.92(18) . . ?
O3 C4 C6 108.86(19) . . ?
O2 C4 C6 108.59(19) . . ?
O3 C4 C5 109.87(19) . . ?
O2 C4 C5 110.2(2) . . ?
C6 C4 C5 114.0(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O4 110.31(19) . . ?
O3 C7 C3 104.77(17) . . ?
O4 C7 C3 106.62(16) . . ?
O3 C7 H7 111.6 . . ?
O4 C7 H7 111.6 . . ?
C3 C7 H7 111.6 . . ?
O4 C8 C2 103.90(18) . . ?
O4 C8 C9 110.86(18) . . ?
C2 C8 C9 115.6(2) . . ?
O4 C8 H8 108.7 . . ?
C2 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
C8 C9 S2 111.92(17) . . ?
C8 C9 H9A 109.2 . . ?
S2 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
S2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?

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
C2 O1 C1 S1 -175.23(17) . . . . ?
C2 O1 C1 S2 4.8(3) . . . . ?
C9 S2 C1 O1 1.5(2) . . . . ?
C9 S2 C1 S1 -178.44(13) . . . . ?
C1 O1 C2 C8 17.7(3) . . . . ?
C1 O1 C2 C3 128.7(2) . . . . ?
C4 O2 C3 C2 131.17(19) . . . . ?
C4 O2 C3 C7 21.8(2) . . . . ?
O1 C2 C3 O2 156.44(16) . . . . ?
C8 C2 C3 O2 -83.0(2) . . . . ?
O1 C2 C3 C7 -93.27(19) . . . . ?
C8 C2 C3 C7 27.3(2) . . . . ?
C7 O3 C4 O2 20.8(2) . . . . ?
C7 O3 C4 C6 136.9(2) . . . . ?
C7 O3 C4 C5 -97.7(2) . . . . ?
C3 O2 C4 O3 -26.5(2) . . . . ?
C3 O2 C4 C6 -142.8(2) . . . . ?
C3 O2 C4 C5 91.7(2) . . . . ?
C4 O3 C7 O4 -121.86(19) . . . . ?
C4 O3 C7 C3 -7.5(2) . . . . ?
C8 O4 C7 O3 91.1(2) . . . . ?
C8 O4 C7 C3 -22.1(2) . . . . ?
O2 C3 C7 O3 -8.8(2) . . . . ?
C2 C3 C7 O3 -121.42(19) . . . . ?
O2 C3 C7 O4 108.15(19) . . . . ?
C2 C3 C7 O4 -4.5(2) . . . . ?
C7 O4 C8 C2 40.6(2) . . . . ?
C7 O4 C8 C9 165.45(19) . . . . ?
O1 C2 C8 O4 72.1(2) . . . . ?
C3 C2 C8 O4 -41.7(2) . . . . ?
O1 C2 C8 C9 -49.6(3) . . . . ?
C3 C2 C8 C9 -163.38(19) . . . . ?
O4 C8 C9 S2 -63.2(2) . . . . ?
C2 C8 C9 S2 54.7(2) . . . . ?
C1 S2 C9 C8 -29.48(19) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.205
_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_s16ab3
_database_code_depnum_ccdc_archive 'CCDC 1583235'
_audit_update_record             
;
2017-10-31 deposited with the CCDC.
2018-02-26 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         'C7 H10 O3 S2'
_chemical_formula_sum            'C7 H10 O3 S2'
_chemical_formula_weight         206.27

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'

_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                   7.55350(10)
_cell_length_b                   12.29650(10)
_cell_length_c                   19.9749(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1855.30(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11259
_cell_measurement_theta_min      4.4170
_cell_measurement_theta_max      72.9980

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.954
_shelx_estimated_absorpt_T_min   0.371
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_T_min  0.36298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.694
_oxdiff_exptl_absorpt_empirical_full_max 1.778
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            17053
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.222
_diffrn_reflns_theta_max         73.152
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3697
_reflns_number_gt                3594
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.999

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SHELXT 
 G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  
;
 SHELXL-2014/8 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0365P)²+0.1689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3697
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.65712(8) 0.74758(5) 0.82879(3) 0.03193(14) Uani 1 1 d . . . . .
S2 S 0.68331(7) 0.95961(4) 0.76868(2) 0.02344(12) Uani 1 1 d . . . . .
O1 O 0.6243(2) 0.96559(13) 0.56949(8) 0.0296(4) Uani 1 1 d . . . . .
O2 O 0.8165(2) 0.87988(13) 0.49576(8) 0.0303(3) Uani 1 1 d . . . . .
O3 O 0.6778(2) 0.76842(11) 0.70059(7) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.6733(3) 0.81892(17) 0.75939(11) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.6806(3) 1.01930(16) 0.68469(11) 0.0257(4) Uani 1 1 d . . . . .
H2A H 0.603184 1.084226 0.683751 0.031 Uiso 1 1 calc R U . . .
H2B H 0.801589 1.041462 0.671333 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6113(3) 0.93374(17) 0.63789(10) 0.0220(4) Uani 1 1 d . . . . .
H3 H 0.485205 0.916934 0.649118 0.026 Uiso 1 1 calc R U . . .
C4 C 0.6555(3) 0.86976(18) 0.52899(11) 0.0271(4) Uani 1 1 d . . . . .
H4 H 0.556826 0.858969 0.496280 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8170(4) 0.9665(2) 0.44816(12) 0.0365(5) Uani 1 1 d . . . . .
H5A H 0.925885 0.963390 0.421584 0.055 Uiso 1 1 calc R U . . .
H5B H 0.810983 1.036314 0.471739 0.055 Uiso 1 1 calc R U . . .
H5C H 0.714280 0.959310 0.418500 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6666(3) 0.77386(18) 0.57728(11) 0.0302(5) Uani 1 1 d . . . . .
H6A H 0.550900 0.736907 0.582117 0.036 Uiso 1 1 calc R U . . .
H6B H 0.756922 0.720394 0.562886 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7207(3) 0.83103(16) 0.64146(10) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.849814 0.848864 0.640588 0.027 Uiso 1 1 calc R U . . .
S3 S 0.79919(8) 0.23117(5) 0.81768(3) 0.03043(14) Uani 1 1 d . . . . .
S4 S 0.82696(7) 0.45010(4) 0.76839(2) 0.02368(12) Uani 1 1 d . . . . .
O4 O 0.8154(2) 0.48346(12) 0.56980(7) 0.0254(3) Uani 1 1 d . . . . .
O5 O 0.6726(2) 0.37982(13) 0.48795(8) 0.0302(3) Uani 1 1 d . . . . .
O6 O 0.8393(2) 0.26864(11) 0.69131(7) 0.0235(3) Uani 1 1 d . . . . .
C11 C 0.8242(3) 0.31085(16) 0.75240(10) 0.0212(4) Uani 1 1 d . . . . .
C12 C 0.8258(3) 0.52116(16) 0.68827(10) 0.0274(4) Uani 1 1 d . . . . .
H12A H 0.739723 0.581854 0.689559 0.033 Uiso 1 1 calc R U . . .
H12B H 0.944577 0.551615 0.678961 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7753(3) 0.44183(16) 0.63442(10) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.646841 0.422810 0.637734 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8275(3) 0.39129(17) 0.52489(10) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.931157 0.400085 0.494213 0.030 Uiso 1 1 calc R U . . .
C15 C 0.6532(3) 0.4632(2) 0.43888(12) 0.0359(5) Uani 1 1 d . . . . .
H15A H 0.545315 0.450265 0.412842 0.054 Uiso 1 1 calc R U . . .
H15B H 0.755961 0.462671 0.408917 0.054 Uiso 1 1 calc R U . . .
H15C H 0.645081 0.534052 0.461164 0.054 Uiso 1 1 calc R U . . .
C16 C 0.8523(3) 0.29025(18) 0.56909(11) 0.0284(5) Uani 1 1 d . . . . .
H16A H 0.744174 0.244739 0.569758 0.034 Uiso 1 1 calc R U . . .
H16B H 0.953706 0.245705 0.553811 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8878(3) 0.34053(16) 0.63700(10) 0.0208(4) Uani 1 1 d . . . . .
H17 H 1.015617 0.360823 0.640775 0.025 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 C1 1.645(2) . ?
S2 C1 1.742(2) . ?
S2 C2 1.831(2) . ?
O1 C3 1.425(2) . ?
O1 C4 1.449(3) . ?
O2 C4 1.391(3) . ?
O2 C5 1.428(3) . ?
O3 C1 1.329(3) . ?
O3 C7 1.447(2) . ?
C2 C3 1.502(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C7 1.511(3) . ?
C3 H3 1.0000 . ?
C4 C6 1.526(3) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.518(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
S3 C11 1.642(2) . ?
S4 C11 1.742(2) . ?
S4 C12 1.823(2) . ?
O4 C13 1.421(2) . ?
O4 C14 1.448(2) . ?
O5 C14 1.390(3) . ?
O5 C15 1.426(3) . ?
O6 C11 1.331(2) . ?
O6 C17 1.447(2) . ?
C12 C13 1.501(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.509(3) . ?
C13 H13 1.0000 . ?
C14 C16 1.536(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.515(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17 1.0000 . ?

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
C1 S2 C2 107.46(10) . . ?
C3 O1 C4 108.85(16) . . ?
C4 O2 C5 112.73(18) . . ?
C1 O3 C7 118.59(16) . . ?
O3 C1 S1 119.83(15) . . ?
O3 C1 S2 123.86(15) . . ?
S1 C1 S2 116.30(12) . . ?
C3 C2 S2 107.06(14) . . ?
C3 C2 H2A 110.3 . . ?
S2 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
S2 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
O1 C3 C2 112.35(17) . . ?
O1 C3 C7 103.73(16) . . ?
C2 C3 C7 111.44(17) . . ?
O1 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C7 C3 H3 109.7 . . ?
O2 C4 O1 109.63(18) . . ?
O2 C4 C6 108.81(19) . . ?
O1 C4 C6 106.54(17) . . ?
O2 C4 H4 110.6 . . ?
O1 C4 H4 110.6 . . ?
C6 C4 H4 110.6 . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 101.00(17) . . ?
C7 C6 H6A 111.6 . . ?
C4 C6 H6A 111.6 . . ?
C7 C6 H6B 111.6 . . ?
C4 C6 H6B 111.6 . . ?
H6A C6 H6B 109.4 . . ?
O3 C7 C3 111.16(16) . . ?
O3 C7 C6 112.51(17) . . ?
C3 C7 C6 101.55(18) . . ?
O3 C7 H7 110.4 . . ?
C3 C7 H7 110.4 . . ?
C6 C7 H7 110.4 . . ?
C11 S4 C12 108.06(10) . . ?
C13 O4 C14 107.11(15) . . ?
C14 O5 C15 112.23(18) . . ?
C11 O6 C17 118.09(15) . . ?
O6 C11 S3 120.35(15) . . ?
O6 C11 S4 123.40(14) . . ?
S3 C11 S4 116.24(12) . . ?
C13 C12 S4 108.58(14) . . ?
C13 C12 H12A 110.0 . . ?
S4 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
S4 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O4 C13 C12 111.25(16) . . ?
O4 C13 C17 102.01(16) . . ?
C12 C13 C17 111.64(17) . . ?
O4 C13 H13 110.6 . . ?
C12 C13 H13 110.6 . . ?
C17 C13 H13 110.6 . . ?
O5 C14 O4 110.78(18) . . ?
O5 C14 C16 109.00(18) . . ?
O4 C14 C16 106.55(16) . . ?
O5 C14 H14 110.1 . . ?
O4 C14 H14 110.1 . . ?
C16 C14 H14 110.1 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 101.90(16) . . ?
C17 C16 H16A 111.4 . . ?
C14 C16 H16A 111.4 . . ?
C17 C16 H16B 111.4 . . ?
C14 C16 H16B 111.4 . . ?
H16A C16 H16B 109.3 . . ?
O6 C17 C13 112.78(16) . . ?
O6 C17 C16 112.16(16) . . ?
C13 C17 C16 101.93(16) . . ?
O6 C17 H17 109.9 . . ?
C13 C17 H17 109.9 . . ?
C16 C17 H17 109.9 . . ?

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
C7 O3 C1 S1 -170.13(15) . . . . ?
C7 O3 C1 S2 10.0(3) . . . . ?
C2 S2 C1 O3 4.9(2) . . . . ?
C2 S2 C1 S1 -175.02(12) . . . . ?
C1 S2 C2 C3 18.40(18) . . . . ?
C4 O1 C3 C2 147.46(18) . . . . ?
C4 O1 C3 C7 27.0(2) . . . . ?
S2 C2 C3 O1 -172.40(14) . . . . ?
S2 C2 C3 C7 -56.5(2) . . . . ?
C5 O2 C4 O1 -65.2(2) . . . . ?
C5 O2 C4 C6 178.66(18) . . . . ?
C3 O1 C4 O2 -119.12(19) . . . . ?
C3 O1 C4 C6 -1.5(2) . . . . ?
O2 C4 C6 C7 94.0(2) . . . . ?
O1 C4 C6 C7 -24.1(2) . . . . ?
C1 O3 C7 C3 -49.2(2) . . . . ?
C1 O3 C7 C6 -162.29(19) . . . . ?
O1 C3 C7 O3 -161.49(16) . . . . ?
C2 C3 C7 O3 77.4(2) . . . . ?
O1 C3 C7 C6 -41.6(2) . . . . ?
C2 C3 C7 C6 -162.71(18) . . . . ?
C4 C6 C7 O3 158.21(17) . . . . ?
C4 C6 C7 C3 39.3(2) . . . . ?
C17 O6 C11 S3 -170.77(14) . . . . ?
C17 O6 C11 S4 10.0(3) . . . . ?
C12 S4 C11 O6 6.8(2) . . . . ?
C12 S4 C11 S3 -172.44(12) . . . . ?
C11 S4 C12 C13 14.65(19) . . . . ?
C14 O4 C13 C12 158.62(18) . . . . ?
C14 O4 C13 C17 39.5(2) . . . . ?
S4 C12 C13 O4 -164.96(14) . . . . ?
S4 C12 C13 C17 -51.7(2) . . . . ?
C15 O5 C14 O4 71.3(2) . . . . ?
C15 O5 C14 C16 -171.80(19) . . . . ?
C13 O4 C14 O5 100.43(19) . . . . ?
C13 O4 C14 C16 -18.0(2) . . . . ?
O5 C14 C16 C17 -130.32(19) . . . . ?
O4 C14 C16 C17 -10.7(2) . . . . ?
C11 O6 C17 C13 -50.2(2) . . . . ?
C11 O6 C17 C16 -164.56(18) . . . . ?
O4 C13 C17 O6 -165.89(15) . . . . ?
C12 C13 C17 O6 75.2(2) . . . . ?
O4 C13 C17 C16 -45.4(2) . . . . ?
C12 C13 C17 C16 -164.32(18) . . . . ?
C14 C16 C17 O6 154.35(17) . . . . ?
C14 C16 C17 C13 33.5(2) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1583234'
_audit_update_record             
;
2017-10-31 deposited with the CCDC.
2018-02-26 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         'C9 H12 O5 S'
_chemical_formula_sum            'C9 H12 O5 S'
_chemical_formula_weight         232.25

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                   6.0784(3)
_cell_length_b                   9.8330(4)
_cell_length_c                   17.9994(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1075.80(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3681
_cell_measurement_theta_min      3.9300
_cell_measurement_theta_max      29.3210

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_T_min  0.94457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.869
_oxdiff_exptl_absorpt_empirical_full_max 1.104
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            9690
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.538
_diffrn_reflns_theta_max         30.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2841
_reflns_number_gt                2475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_max     0.828
_reflns_Friedel_fraction_full    1.000

_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SHELXT 
G.M.Sheldrick,Acta Crystallogr.,Sect. A: Found.Crystallogr., 2008, 64,112-122.
;
_computing_structure_refinement  
;
 SHELXL-2016/6 (Sheldrick, 2016)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0293P)²+0.3431P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 827 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
S S 0.88411(12) 0.35331(6) 0.32306(4) 0.03367(18) Uani 1 1 d . . . . .
O1 O 0.5083(3) 0.46779(18) 0.30768(11) 0.0314(5) Uani 1 1 d . . . . .
O2 O 0.4399(3) 0.68498(17) 0.41479(9) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.4807(4) 0.89738(19) 0.46698(11) 0.0409(6) Uani 1 1 d . . . . .
O4 O 0.6879(3) 0.95754(17) 0.36741(10) 0.0279(4) Uani 1 1 d . . . . .
O5 O 0.8055(3) 0.61073(16) 0.31962(11) 0.0264(4) Uani 1 1 d . . . . .
C1 C 0.7208(4) 0.4864(2) 0.31640(14) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.3558(5) 0.5804(3) 0.29830(17) 0.0316(6) Uani 1 1 d . . . . .
H2A H 0.210931 0.555118 0.319256 0.038 Uiso 1 1 calc R U . . .
H2B H 0.335896 0.598924 0.244654 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4377(4) 0.7057(3) 0.33587(13) 0.0242(5) Uani 1 1 d . . . . .
H3 H 0.343247 0.785419 0.322782 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5897(5) 0.7781(2) 0.44588(13) 0.0251(5) Uani 1 1 d . . . . .
H4 H 0.671307 0.737053 0.488586 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5754(5) 1.0127(3) 0.43055(14) 0.0318(6) Uani 1 1 d . . . . .
C6 C 0.3931(6) 1.1036(3) 0.4034(2) 0.0509(9) Uani 1 1 d . . . . .
H6A H 0.301729 1.053859 0.367712 0.076 Uiso 1 1 calc R U . . .
H6B H 0.456422 1.183862 0.379211 0.076 Uiso 1 1 calc R U . . .
H6C H 0.302441 1.132324 0.445607 0.076 Uiso 1 1 calc R U . . .
C7 C 0.7357(7) 1.0827(3) 0.48160(17) 0.0451(9) Uani 1 1 d . . . . .
H7A H 0.851223 1.018545 0.496245 0.068 Uiso 1 1 calc R U . . .
H7B H 0.658094 1.114841 0.525977 0.068 Uiso 1 1 calc R U . . .
H7C H 0.802110 1.160274 0.455808 0.068 Uiso 1 1 calc R U . . .
C8 C 0.7476(4) 0.8215(2) 0.38334(13) 0.0223(5) Uani 1 1 d . . . . .
H8 H 0.906524 0.810227 0.396376 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6750(4) 0.7348(2) 0.31782(14) 0.0217(5) Uani 1 1 d . . . . .
H9 H 0.691087 0.784145 0.269559 0.026 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
S C1 1.647(3) . ?
O1 C1 1.314(3) . ?
O1 C2 1.454(3) . ?
O2 C4 1.407(3) . ?
O2 C3 1.435(3) . ?
O3 C4 1.400(3) . ?
O3 C5 1.431(3) . ?
O4 C8 1.415(3) . ?
O4 C5 1.433(3) . ?
O5 C1 1.328(3) . ?
O5 C9 1.455(3) . ?
C2 C3 1.490(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C9 1.506(3) . ?
C3 H3 1.0000 . ?
C4 C8 1.540(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.506(4) . ?
C5 C7 1.506(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.521(3) . ?
C8 H8 1.0000 . ?
C9 H9 1.0000 . ?

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
C1 O1 C2 122.3(2) . . ?
C4 O2 C3 107.91(18) . . ?
C4 O3 C5 110.5(2) . . ?
C8 O4 C5 108.61(19) . . ?
C1 O5 C9 124.03(18) . . ?
O1 C1 O5 120.9(2) . . ?
O1 C1 S 119.40(19) . . ?
O5 C1 S 119.65(19) . . ?
O1 C2 C3 111.3(2) . . ?
O1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O2 C3 C2 109.6(2) . . ?
O2 C3 C9 103.4(2) . . ?
C2 C3 C9 112.3(2) . . ?
O2 C3 H3 110.5 . . ?
C2 C3 H3 110.5 . . ?
C9 C3 H3 110.5 . . ?
O3 C4 O2 110.3(2) . . ?
O3 C4 C8 105.13(19) . . ?
O2 C4 C8 107.05(18) . . ?
O3 C4 H4 111.4 . . ?
O2 C4 H4 111.4 . . ?
C8 C4 H4 111.4 . . ?
O3 C5 O4 104.82(19) . . ?
O3 C5 C6 108.9(3) . . ?
O4 C5 C6 108.6(2) . . ?
O3 C5 C7 110.1(2) . . ?
O4 C5 C7 110.4(3) . . ?
C6 C5 C7 113.7(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 C9 107.4(2) . . ?
O4 C8 C4 104.5(2) . . ?
C9 C8 C4 103.32(19) . . ?
O4 C8 H8 113.6 . . ?
C9 C8 H8 113.6 . . ?
C4 C8 H8 113.6 . . ?
O5 C9 C3 110.97(19) . . ?
O5 C9 C8 107.14(19) . . ?
C3 C9 C8 102.6(2) . . ?
O5 C9 H9 111.9 . . ?
C3 C9 H9 111.9 . . ?
C8 C9 H9 111.9 . . ?

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
C2 O1 C1 O5 2.4(4) . . . . ?
C2 O1 C1 S -177.36(19) . . . . ?
C9 O5 C1 O1 3.3(4) . . . . ?
C9 O5 C1 S -176.99(18) . . . . ?
C1 O1 C2 C3 -28.5(4) . . . . ?
C4 O2 C3 C2 157.9(2) . . . . ?
C4 O2 C3 C9 38.1(2) . . . . ?
O1 C2 C3 O2 -66.4(3) . . . . ?
O1 C2 C3 C9 47.8(3) . . . . ?
C5 O3 C4 O2 -122.5(2) . . . . ?
C5 O3 C4 C8 -7.4(3) . . . . ?
C3 O2 C4 O3 92.5(2) . . . . ?
C3 O2 C4 C8 -21.4(3) . . . . ?
C4 O3 C5 O4 20.7(3) . . . . ?
C4 O3 C5 C6 136.7(2) . . . . ?
C4 O3 C5 C7 -98.0(3) . . . . ?
C8 O4 C5 O3 -26.4(3) . . . . ?
C8 O4 C5 C6 -142.7(2) . . . . ?
C8 O4 C5 C7 92.0(3) . . . . ?
C5 O4 C8 C9 131.0(2) . . . . ?
C5 O4 C8 C4 21.7(3) . . . . ?
O3 C4 C8 O4 -8.7(3) . . . . ?
O2 C4 C8 O4 108.6(2) . . . . ?
O3 C4 C8 C9 -120.9(2) . . . . ?
O2 C4 C8 C9 -3.6(3) . . . . ?
C1 O5 C9 C3 17.7(3) . . . . ?
C1 O5 C9 C8 128.9(2) . . . . ?
O2 C3 C9 O5 75.4(2) . . . . ?
C2 C3 C9 O5 -42.6(3) . . . . ?
O2 C3 C9 C8 -38.7(2) . . . . ?
C2 C3 C9 C8 -156.7(2) . . . . ?
O4 C8 C9 O5 158.48(19) . . . . ?
C4 C8 C9 O5 -91.4(2) . . . . ?
O4 C8 C9 C3 -84.6(2) . . . . ?
C4 C8 C9 C3 25.5(2) . . . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050

