# Electronic Supplementary Material (ESI) for Green 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. 
# 
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data_ma108
_database_code_depnum_ccdc_archive 'CCDC 1578047'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2018-06-04 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         'C22 H16 O5 S'
_chemical_formula_sum            'C22 H16 O5 S'
_chemical_formula_weight         392.41

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.7651(6)
_cell_length_b                   16.4066(12)
_cell_length_c                   14.1404(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1801.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8840
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      25.82

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8840
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.240
_diffrn_reflns_theta_max         25.639
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3312
_reflns_number_gt                2944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_max     0.956
_reflns_Friedel_fraction_full    0.970

_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_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)+(0.0351P)²] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0072(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1230 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3312
_refine_ls_number_parameters     255
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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 0.72770(9) 0.45046(4) 0.62285(5) 0.02230(17) Uani 1 1 d . . . . .
O1 O 0.6038(3) 0.59661(12) 0.83872(14) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.5974(3) 0.46392(12) 0.81795(14) 0.0318(5) Uani 1 1 d . . . . .
O3 O 0.7586(3) 0.90992(12) 0.72530(14) 0.0290(5) Uani 1 1 d . . . . .
O4 O 0.7888(3) 0.46900(13) 0.52939(15) 0.0301(5) Uani 1 1 d . . . . .
O5 O 0.8238(3) 0.39328(13) 0.67911(16) 0.0322(5) Uani 1 1 d . . . . .
C1 C 0.6343(4) 0.52874(18) 0.7844(2) 0.0231(7) Uani 1 1 d . . . . .
C2 C 0.7071(4) 0.54333(17) 0.68944(19) 0.0222(6) Uani 1 1 d . . . . .
C3 C 0.7462(4) 0.61935(17) 0.6563(2) 0.0199(6) Uani 1 1 d . . . . .
C4 C 0.7150(4) 0.68842(17) 0.7192(2) 0.0211(6) Uani 1 1 d . . . . .
C5 C 0.7526(4) 0.76993(17) 0.69441(19) 0.0215(6) Uani 1 1 d . . . . .
H5 H 0.802256 0.781541 0.634508 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7176(4) 0.83328(18) 0.7568(2) 0.0232(6) Uani 1 1 d . . . . .
C7 C 0.6449(4) 0.81700(18) 0.8455(2) 0.0261(7) Uani 1 1 d . . . . .
H7 H 0.620536 0.860484 0.887786 0.031 Uiso 1 1 calc R U . . .
C8 C 0.6084(4) 0.7371(2) 0.8715(2) 0.0267(7) Uani 1 1 d . . . . .
H8 H 0.559998 0.725539 0.931763 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6435(4) 0.67443(17) 0.80869(19) 0.0230(6) Uani 1 1 d . . . . .
C10 C 0.6978(5) 0.97826(19) 0.7811(2) 0.0315(8) Uani 1 1 d . . . . .
H10A H 0.572437 0.974885 0.787885 0.047 Uiso 1 1 calc R U . . .
H10B H 0.728303 1.029343 0.749286 0.047 Uiso 1 1 calc R U . . .
H10C H 0.751648 0.976746 0.843731 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5136(4) 0.41532(16) 0.6115(2) 0.0214(6) Uani 1 1 d . . . . .
C12 C 0.4637(4) 0.34518(18) 0.6587(2) 0.0261(6) Uani 1 1 d . . . . .
H12 H 0.540570 0.319118 0.701351 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3012(4) 0.31344(19) 0.6432(2) 0.0307(8) Uani 1 1 d . . . . .
H13 H 0.267334 0.264363 0.673595 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1874(5) 0.3534(2) 0.5830(2) 0.0327(8) Uani 1 1 d . . . . .
H14 H 0.075607 0.331727 0.572510 0.039 Uiso 1 1 calc R U . . .
C15 C 0.2372(4) 0.42518(19) 0.5382(2) 0.0306(7) Uani 1 1 d . . . . .
H15 H 0.157678 0.453197 0.498816 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4014(4) 0.45605(18) 0.5504(2) 0.0258(7) Uani 1 1 d . . . . .
H16 H 0.437082 0.503895 0.518051 0.031 Uiso 1 1 calc R U . . .
C31 C 0.8160(4) 0.63549(17) 0.55944(19) 0.0207(6) Uani 1 1 d . . . . .
C32 C 0.7071(5) 0.6671(2) 0.4906(2) 0.0323(8) Uani 1 1 d . . . . .
H32 H 0.591759 0.680838 0.506202 0.039 Uiso 1 1 calc R U . . .
C33 C 0.7670(5) 0.6787(2) 0.3984(2) 0.0391(9) Uani 1 1 d . . . . .
H33 H 0.691750 0.699153 0.351082 0.047 Uiso 1 1 calc R U . . .
C34 C 0.9357(5) 0.6605(2) 0.3763(2) 0.0341(8) Uani 1 1 d . . . . .
H34 H 0.976296 0.667971 0.313538 0.041 Uiso 1 1 calc R U . . .
C35 C 1.0460(5) 0.63133(19) 0.4455(2) 0.0311(7) Uani 1 1 d . . . . .
H35 H 1.162596 0.619835 0.430076 0.037 Uiso 1 1 calc R U . . .
C36 C 0.9872(4) 0.61873(18) 0.5374(2) 0.0252(7) Uani 1 1 d . . . . .
H36 H 1.063299 0.598852 0.584656 0.030 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 O4 1.437(2) . ?
S1 O5 1.439(2) . ?
S1 C11 1.767(3) . ?
S1 C2 1.798(3) . ?
O1 C1 1.374(4) . ?
O1 C9 1.380(3) . ?
O2 C1 1.199(4) . ?
O3 C6 1.371(4) . ?
O3 C10 1.450(4) . ?
C1 C2 1.476(4) . ?
C2 C3 1.366(4) . ?
C3 C4 1.461(4) . ?
C3 C31 1.497(4) . ?
C4 C9 1.401(4) . ?
C4 C5 1.413(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(4) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.386(4) . ?
C11 C16 1.397(4) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C31 C32 1.390(4) . ?
C31 C36 1.393(4) . ?
C32 C33 1.396(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.393(4) . ?
C35 H35 0.9500 . ?
C36 H36 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
O4 S1 O5 118.39(13) . . ?
O4 S1 C11 107.23(14) . . ?
O5 S1 C11 108.99(13) . . ?
O4 S1 C2 109.36(13) . . ?
O5 S1 C2 108.00(13) . . ?
C11 S1 C2 103.92(13) . . ?
C1 O1 C9 122.6(2) . . ?
C6 O3 C10 117.2(2) . . ?
O2 C1 O1 117.1(2) . . ?
O2 C1 C2 126.5(3) . . ?
O1 C1 C2 116.3(2) . . ?
C3 C2 C1 123.0(3) . . ?
C3 C2 S1 125.0(2) . . ?
C1 C2 S1 111.9(2) . . ?
C2 C3 C4 117.5(3) . . ?
C2 C3 C31 123.8(3) . . ?
C4 C3 C31 118.7(2) . . ?
C9 C4 C5 117.5(2) . . ?
C9 C4 C3 119.3(3) . . ?
C5 C4 C3 123.3(3) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O3 C6 C5 115.8(2) . . ?
O3 C6 C7 124.0(3) . . ?
C5 C6 C7 120.3(3) . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O1 C9 C8 116.4(2) . . ?
O1 C9 C4 121.2(2) . . ?
C8 C9 C4 122.4(3) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 121.4(3) . . ?
C12 C11 S1 119.3(2) . . ?
C16 C11 S1 119.1(2) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 118.5(3) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?
C32 C31 C36 119.8(3) . . ?
C32 C31 C3 119.2(3) . . ?
C36 C31 C3 121.0(3) . . ?
C31 C32 C33 120.1(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 119.9(3) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 120.1(3) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C34 C35 C36 120.5(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 119.5(3) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 O2 178.8(3) . . . . ?
C9 O1 C1 C2 -2.1(4) . . . . ?
O2 C1 C2 C3 -179.9(3) . . . . ?
O1 C1 C2 C3 1.2(4) . . . . ?
O2 C1 C2 S1 2.8(4) . . . . ?
O1 C1 C2 S1 -176.2(2) . . . . ?
O4 S1 C2 C3 -0.9(3) . . . . ?
O5 S1 C2 C3 129.2(3) . . . . ?
C11 S1 C2 C3 -115.1(3) . . . . ?
O4 S1 C2 C1 176.4(2) . . . . ?
O5 S1 C2 C1 -53.5(2) . . . . ?
C11 S1 C2 C1 62.2(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
S1 C2 C3 C4 177.6(2) . . . . ?
C1 C2 C3 C31 -178.4(3) . . . . ?
S1 C2 C3 C31 -1.4(4) . . . . ?
C2 C3 C4 C9 -1.5(4) . . . . ?
C31 C3 C4 C9 177.5(3) . . . . ?
C2 C3 C4 C5 178.8(3) . . . . ?
C31 C3 C4 C5 -2.1(4) . . . . ?
C9 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C10 O3 C6 C5 169.8(3) . . . . ?
C10 O3 C6 C7 -10.2(4) . . . . ?
C4 C5 C6 O3 -179.8(3) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
O3 C6 C7 C8 -179.6(3) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C1 O1 C9 C8 -178.9(3) . . . . ?
C1 O1 C9 C4 1.2(4) . . . . ?
C7 C8 C9 O1 -179.8(3) . . . . ?
C7 C8 C9 C4 0.1(5) . . . . ?
C5 C4 C9 O1 -179.6(3) . . . . ?
C3 C4 C9 O1 0.7(4) . . . . ?
C5 C4 C9 C8 0.5(4) . . . . ?
C3 C4 C9 C8 -179.2(3) . . . . ?
O4 S1 C11 C12 132.9(2) . . . . ?
O5 S1 C11 C12 3.6(3) . . . . ?
C2 S1 C11 C12 -111.4(2) . . . . ?
O4 S1 C11 C16 -43.2(2) . . . . ?
O5 S1 C11 C16 -172.5(2) . . . . ?
C2 S1 C11 C16 72.5(2) . . . . ?
C16 C11 C12 C13 1.8(4) . . . . ?
S1 C11 C12 C13 -174.2(2) . . . . ?
C11 C12 C13 C14 -2.1(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 2.1(4) . . . . ?
C14 C15 C16 C11 -2.4(4) . . . . ?
C12 C11 C16 C15 0.4(4) . . . . ?
S1 C11 C16 C15 176.4(2) . . . . ?
C2 C3 C31 C32 104.0(4) . . . . ?
C4 C3 C31 C32 -75.1(4) . . . . ?
C2 C3 C31 C36 -75.5(4) . . . . ?
C4 C3 C31 C36 105.4(3) . . . . ?
C36 C31 C32 C33 2.8(5) . . . . ?
C3 C31 C32 C33 -176.7(3) . . . . ?
C31 C32 C33 C34 -1.5(5) . . . . ?
C32 C33 C34 C35 -0.5(5) . . . . ?
C33 C34 C35 C36 1.2(5) . . . . ?
C32 C31 C36 C35 -2.1(4) . . . . ?
C3 C31 C36 C35 177.4(3) . . . . ?
C34 C35 C36 C31 0.2(4) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_ma109
_database_code_depnum_ccdc_archive 'CCDC 1578048'
_audit_update_record             
;
2017-10-04 deposited with the CCDC.
2018-06-04 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         'C21 H13 Cl O4 S'
_chemical_formula_sum            'C21 H13 Cl O4 S'
_chemical_formula_weight         396.82

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'
Cl Cl 0.1484 0.1585 '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           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   12.8859(12)
_cell_length_b                   5.6317(3)
_cell_length_c                   25.025(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.804(8)
_cell_angle_gamma                90
_cell_volume                     1813.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    19801
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.351
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'MULABS (Spek, 2003; Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17139
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         25.517
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6690
_reflns_number_gt                5144
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_max     0.986
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1460P)²] 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 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   -0.05(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6690
_refine_ls_number_parameters     487
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1858
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.953
_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
Cl1 Cl 0.31913(18) 0.0403(5) 0.56500(12) 0.0606(7) Uani 1 1 d . . . . .
S1 S 0.73707(15) 1.1328(4) 0.49168(8) 0.0418(5) Uani 1 1 d . . . . .
O1 O 0.4870(4) 0.7191(12) 0.4724(2) 0.0441(14) Uani 1 1 d . . . . .
O2 O 0.5450(5) 1.0226(13) 0.4273(2) 0.0497(15) Uani 1 1 d . . . . .
O3 O 0.8224(5) 1.1066(15) 0.5303(2) 0.0585(18) Uani 1 1 d . . . . .
O4 O 0.6928(5) 1.3622(13) 0.4832(3) 0.0535(16) Uani 1 1 d . . . . .
C1 C 0.5559(6) 0.9029(18) 0.4668(3) 0.044(2) Uani 1 1 d . . . . .
C2 C 0.6385(6) 0.9277(16) 0.5097(3) 0.0376(17) Uani 1 1 d . . . . .
C3 C 0.6386(6) 0.8062(16) 0.5559(3) 0.0386(18) Uani 1 1 d . . . . .
C4 C 0.5550(6) 0.6335(16) 0.5625(3) 0.0381(18) Uani 1 1 d . . . . .
C5 C 0.5407(6) 0.5044(18) 0.6092(4) 0.046(2) Uani 1 1 d . . . . .
H5 H 0.5828 0.5396 0.6405 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4670(7) 0.3270(18) 0.6111(4) 0.049(2) Uani 1 1 d . . . . .
H6 H 0.4584 0.2402 0.6431 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4053(6) 0.2776(17) 0.5649(4) 0.047(2) Uani 1 1 d . . . . .
C8 C 0.4117(6) 0.4067(18) 0.5190(4) 0.046(2) Uani 1 1 d . . . . .
H8 H 0.3678 0.3736 0.4883 0.055 Uiso 1 1 calc R U . . .
C9 C 0.4847(6) 0.5880(16) 0.5188(3) 0.0414(19) Uani 1 1 d . . . . .
C11 C 0.7780(6) 1.0208(17) 0.4297(3) 0.0413(19) Uani 1 1 d . . . . .
C12 C 0.8336(7) 0.8119(19) 0.4300(4) 0.053(2) Uani 1 1 d . . . . .
H12 H 0.8478 0.7250 0.4620 0.063 Uiso 1 1 calc R U . . .
C13 C 0.8682(8) 0.734(2) 0.3810(5) 0.058(3) Uani 1 1 d . . . . .
H13 H 0.9058 0.5889 0.3798 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8499(7) 0.859(2) 0.3349(4) 0.059(3) Uani 1 1 d . . . . .
H14 H 0.8753 0.8029 0.3022 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7938(7) 1.069(2) 0.3361(4) 0.055(2) Uani 1 1 d . . . . .
H15 H 0.7809 1.1573 0.3041 0.066 Uiso 1 1 calc R U . . .
C16 C 0.7567(7) 1.151(2) 0.3836(3) 0.048(2) Uani 1 1 d . . . . .
H16 H 0.7174 1.2934 0.3846 0.058 Uiso 1 1 calc R U . . .
C31 C 0.7183(6) 0.8207(17) 0.6018(3) 0.0400(19) Uani 1 1 d . . . . .
C32 C 0.7185(7) 1.0089(18) 0.6371(4) 0.049(2) Uani 1 1 d . . . . .
H32 H 0.6704 1.1352 0.6314 0.058 Uiso 1 1 calc R U . . .
C33 C 0.7888(8) 1.014(2) 0.6812(4) 0.054(2) Uani 1 1 d . . . . .
H33 H 0.7880 1.1436 0.7056 0.065 Uiso 1 1 calc R U . . .
C34 C 0.8580(7) 0.837(2) 0.6893(3) 0.049(2) Uani 1 1 d . . . . .
H34 H 0.9057 0.8421 0.7195 0.059 Uiso 1 1 calc R U . . .
C35 C 0.8603(7) 0.6489(19) 0.6545(4) 0.051(2) Uani 1 1 d . . . . .
H35 H 0.9097 0.5252 0.6602 0.062 Uiso 1 1 calc R U . . .
C36 C 0.7896(7) 0.6413(18) 0.6108(4) 0.048(2) Uani 1 1 d . . . . .
H36 H 0.7905 0.5106 0.5868 0.058 Uiso 1 1 calc R U . . .
Cl1A Cl 0.1317(2) -0.2300(6) 0.45703(11) 0.0703(8) Uani 1 1 d . . . . .
S1A S 0.22802(14) 0.8230(4) 0.22305(8) 0.0391(5) Uani 1 1 d . . . . .
O1A O 0.0659(4) 0.4064(13) 0.3180(2) 0.0456(14) Uani 1 1 d . . . . .
O2A O 0.0223(5) 0.6609(13) 0.2542(3) 0.0523(16) Uani 1 1 d . . . . .
O3A O 0.1840(5) 1.0428(12) 0.2398(3) 0.0518(16) Uani 1 1 d . . . . .
O4A O 0.3371(4) 0.8197(11) 0.2132(2) 0.0433(14) Uani 1 1 d . . . . .
C1A C 0.0928(6) 0.5671(16) 0.2798(3) 0.0388(18) Uani 1 1 d . . . . .
C2A C 0.2042(6) 0.6070(15) 0.2728(3) 0.0357(17) Uani 1 1 d . . . . .
C3A C 0.2787(6) 0.4849(16) 0.3020(3) 0.0364(17) Uani 1 1 d . . . . .
C4A C 0.2462(6) 0.3223(16) 0.3423(3) 0.0361(17) Uani 1 1 d . . . . .
C5A C 0.3163(7) 0.1915(17) 0.3764(3) 0.0420(19) Uani 1 1 d . . . . .
H5A H 0.3889 0.2186 0.3750 0.050 Uiso 1 1 calc R U . . .
C6A C 0.2806(6) 0.0265(17) 0.4113(3) 0.0422(19) Uani 1 1 d . . . . .
H6A H 0.3283 -0.0620 0.4335 0.051 Uiso 1 1 calc R U . . .
C7A C 0.1738(7) -0.0116(19) 0.4142(4) 0.049(2) Uani 1 1 d . . . . .
C8A C 0.1030(7) 0.1199(19) 0.3839(4) 0.048(2) Uani 1 1 d . . . . .
H8A H 0.0305 0.0994 0.3874 0.057 Uiso 1 1 calc R U . . .
C9A C 0.1399(6) 0.2825(17) 0.3483(3) 0.0426(19) Uani 1 1 d . . . . .
C11A C 0.1598(6) 0.7243(15) 0.1642(3) 0.0375(17) Uani 1 1 d . . . . .
C12A C 0.1881(7) 0.5137(17) 0.1400(3) 0.043(2) Uani 1 1 d . . . . .
H12A H 0.2406 0.4145 0.1559 0.052 Uiso 1 1 calc R U . . .
C13A C 0.1376(8) 0.4532(19) 0.0922(4) 0.052(2) Uani 1 1 d . . . . .
H13A H 0.1550 0.3087 0.0752 0.062 Uiso 1 1 calc R U . . .
C14A C 0.0618(8) 0.599(2) 0.0683(4) 0.054(2) Uani 1 1 d . . . . .
H14A H 0.0283 0.5540 0.0351 0.064 Uiso 1 1 calc R U . . .
C15A C 0.0353(7) 0.8079(19) 0.0927(4) 0.053(2) Uani 1 1 d . . . . .
H15A H -0.0161 0.9085 0.0762 0.063 Uiso 1 1 calc R U . . .
C16A C 0.0837(6) 0.8722(17) 0.1416(3) 0.0423(19) Uani 1 1 d . . . . .
H16A H 0.0650 1.0144 0.1591 0.051 Uiso 1 1 calc R U . . .
C31A C 0.3935(5) 0.5043(15) 0.2941(3) 0.0352(17) Uani 1 1 d . . . . .
C32A C 0.4538(7) 0.674(2) 0.3201(4) 0.051(2) Uani 1 1 d . . . . .
H32A H 0.4226 0.7841 0.3431 0.061 Uiso 1 1 calc R U . . .
C33A C 0.5603(7) 0.685(2) 0.3131(5) 0.059(3) Uani 1 1 d . . . . .
H33A H 0.6012 0.8047 0.3308 0.071 Uiso 1 1 calc R U . . .
C34A C 0.6058(7) 0.524(2) 0.2806(4) 0.056(3) Uani 1 1 d . . . . .
H34A H 0.6783 0.5321 0.2756 0.068 Uiso 1 1 calc R U . . .
C35A C 0.5471(7) 0.3488(19) 0.2550(4) 0.051(2) Uani 1 1 d . . . . .
H35A H 0.5793 0.2366 0.2328 0.062 Uiso 1 1 calc R U . . .
C36A C 0.4413(7) 0.3375(17) 0.2619(4) 0.046(2) Uani 1 1 d . . . . .
H36A H 0.4010 0.2160 0.2447 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.738(9) . ?
S1 O4 1.424(8) . ?
S1 O3 1.436(7) . ?
S1 C11 1.778(9) . ?
S1 C2 1.791(9) . ?
O1 C1 1.375(11) . ?
O1 C9 1.378(11) . ?
O2 C1 1.198(11) . ?
C1 C2 1.481(11) . ?
C2 C3 1.344(12) . ?
C3 C4 1.466(12) . ?
C3 C31 1.506(11) . ?
C4 C5 1.398(13) . ?
C4 C9 1.409(12) . ?
C5 C6 1.381(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.366(14) . ?
C8 C9 1.388(13) . ?
C8 H8 0.9500 . ?
C11 C12 1.378(14) . ?
C11 C16 1.382(13) . ?
C12 C13 1.396(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C31 C36 1.377(13) . ?
C31 C32 1.380(13) . ?
C32 C33 1.393(12) . ?
C32 H32 0.9500 . ?
C33 C34 1.348(15) . ?
C33 H33 0.9500 . ?
C34 C35 1.374(15) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(13) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
Cl1A C7A 1.736(10) . ?
S1A O3A 1.433(7) . ?
S1A O4A 1.439(6) . ?
S1A C11A 1.768(8) . ?
S1A C2A 1.777(9) . ?
O1A C1A 1.373(11) . ?
O1A C9A 1.378(11) . ?
O2A C1A 1.207(10) . ?
C1A C2A 1.472(11) . ?
C2A C3A 1.363(12) . ?
C3A C4A 1.441(12) . ?
C3A C31A 1.506(10) . ?
C4A C9A 1.404(11) . ?
C4A C5A 1.417(12) . ?
C5A C6A 1.371(13) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.398(12) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.374(14) . ?
C8A C9A 1.378(13) . ?
C8A H8A 0.9500 . ?
C11A C16A 1.385(12) . ?
C11A C12A 1.388(12) . ?
C12A C13A 1.376(13) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.387(15) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.379(15) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.394(13) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C31A C32A 1.374(13) . ?
C31A C36A 1.401(12) . ?
C32A C33A 1.393(13) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.372(16) . ?
C33A H33A 0.9500 . ?
C34A C35A 1.379(15) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.384(12) . ?
C35A H35A 0.9500 . ?
C36A H36A 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
O4 S1 O3 118.8(5) . . ?
O4 S1 C11 109.0(4) . . ?
O3 S1 C11 107.5(4) . . ?
O4 S1 C2 109.8(4) . . ?
O3 S1 C2 107.1(4) . . ?
C11 S1 C2 103.6(4) . . ?
C1 O1 C9 122.0(7) . . ?
O2 C1 O1 117.2(8) . . ?
O2 C1 C2 126.6(8) . . ?
O1 C1 C2 116.2(8) . . ?
C3 C2 C1 123.2(8) . . ?
C3 C2 S1 125.0(6) . . ?
C1 C2 S1 111.8(6) . . ?
C2 C3 C4 117.6(7) . . ?
C2 C3 C31 127.0(8) . . ?
C4 C3 C31 115.4(7) . . ?
C5 C4 C9 116.7(8) . . ?
C5 C4 C3 124.5(8) . . ?
C9 C4 C3 118.8(8) . . ?
C6 C5 C4 121.6(9) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 118.7(9) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 122.3(8) . . ?
C8 C7 Cl1 118.4(8) . . ?
C6 C7 Cl1 119.3(8) . . ?
C7 C8 C9 117.6(9) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
O1 C9 C8 116.1(8) . . ?
O1 C9 C4 121.1(8) . . ?
C8 C9 C4 122.8(9) . . ?
C12 C11 C16 122.6(9) . . ?
C12 C11 S1 118.4(7) . . ?
C16 C11 S1 119.0(7) . . ?
C11 C12 C13 117.0(10) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C14 C13 C12 122.1(10) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.4(9) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.4(10) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C11 C16 C15 118.6(10) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C36 C31 C32 118.6(8) . . ?
C36 C31 C3 120.6(8) . . ?
C32 C31 C3 120.7(8) . . ?
C31 C32 C33 120.3(8) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 120.2(9) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 120.6(8) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 119.4(9) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C31 C36 C35 120.8(9) . . ?
C31 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
O3A S1A O4A 117.7(4) . . ?
O3A S1A C11A 109.1(4) . . ?
O4A S1A C11A 107.6(4) . . ?
O3A S1A C2A 107.6(4) . . ?
O4A S1A C2A 108.3(4) . . ?
C11A S1A C2A 105.8(4) . . ?
C1A O1A C9A 121.7(6) . . ?
O2A C1A O1A 116.7(7) . . ?
O2A C1A C2A 125.6(8) . . ?
O1A C1A C2A 117.7(7) . . ?
C3A C2A C1A 121.6(8) . . ?
C3A C2A S1A 125.4(6) . . ?
C1A C2A S1A 113.0(6) . . ?
C2A C3A C4A 118.4(7) . . ?
C2A C3A C31A 124.3(7) . . ?
C4A C3A C31A 117.3(7) . . ?
C9A C4A C5A 116.7(8) . . ?
C9A C4A C3A 119.6(7) . . ?
C5A C4A C3A 123.6(7) . . ?
C6A C5A C4A 120.8(8) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C5A C6A C7A 120.0(8) . . ?
C5A C6A H6A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C8A C7A C6A 121.1(8) . . ?
C8A C7A Cl1A 120.3(7) . . ?
C6A C7A Cl1A 118.6(7) . . ?
C7A C8A C9A 118.3(8) . . ?
C7A C8A H8A 120.8 . . ?
C9A C8A H8A 120.8 . . ?
C8A C9A O1A 116.2(7) . . ?
C8A C9A C4A 123.0(8) . . ?
O1A C9A C4A 120.9(7) . . ?
C16A C11A C12A 122.1(8) . . ?
C16A C11A S1A 117.6(7) . . ?
C12A C11A S1A 120.1(6) . . ?
C13A C12A C11A 117.9(8) . . ?
C13A C12A H12A 121.1 . . ?
C11A C12A H12A 121.1 . . ?
C12A C13A C14A 121.4(9) . . ?
C12A C13A H13A 119.3 . . ?
C14A C13A H13A 119.3 . . ?
C15A C14A C13A 119.9(9) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
C14A C15A C16A 120.1(9) . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C11A C16A C15A 118.6(9) . . ?
C11A C16A H16A 120.7 . . ?
C15A C16A H16A 120.7 . . ?
C32A C31A C36A 118.9(7) . . ?
C32A C31A C3A 121.7(7) . . ?
C36A C31A C3A 119.2(7) . . ?
C31A C32A C33A 120.7(9) . . ?
C31A C32A H32A 119.6 . . ?
C33A C32A H32A 119.6 . . ?
C34A C33A C32A 119.7(9) . . ?
C34A C33A H33A 120.1 . . ?
C32A C33A H33A 120.1 . . ?
C33A C34A C35A 120.6(9) . . ?
C33A C34A H34A 119.7 . . ?
C35A C34A H34A 119.7 . . ?
C34A C35A C36A 119.8(9) . . ?
C34A C35A H35A 120.1 . . ?
C36A C35A H35A 120.1 . . ?
C35A C36A C31A 120.3(9) . . ?
C35A C36A H36A 119.9 . . ?
C31A C36A H36A 119.9 . . ?

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
C9 O1 C1 O2 -172.3(8) . . . . ?
C9 O1 C1 C2 9.5(11) . . . . ?
O2 C1 C2 C3 171.6(9) . . . . ?
O1 C1 C2 C3 -10.4(12) . . . . ?
O2 C1 C2 S1 -9.4(12) . . . . ?
O1 C1 C2 S1 168.6(6) . . . . ?
O4 S1 C2 C3 -119.6(8) . . . . ?
O3 S1 C2 C3 10.7(9) . . . . ?
C11 S1 C2 C3 124.2(8) . . . . ?
O4 S1 C2 C1 61.5(7) . . . . ?
O3 S1 C2 C1 -168.2(6) . . . . ?
C11 S1 C2 C1 -54.8(7) . . . . ?
C1 C2 C3 C4 2.8(12) . . . . ?
S1 C2 C3 C4 -176.0(6) . . . . ?
C1 C2 C3 C31 -179.5(8) . . . . ?
S1 C2 C3 C31 1.6(13) . . . . ?
C2 C3 C4 C5 -175.8(8) . . . . ?
C31 C3 C4 C5 6.3(12) . . . . ?
C2 C3 C4 C9 5.6(12) . . . . ?
C31 C3 C4 C9 -172.3(7) . . . . ?
C9 C4 C5 C6 5.3(12) . . . . ?
C3 C4 C5 C6 -173.3(8) . . . . ?
C4 C5 C6 C7 -0.3(13) . . . . ?
C5 C6 C7 C8 -3.5(13) . . . . ?
C5 C6 C7 Cl1 175.1(7) . . . . ?
C6 C7 C8 C9 1.8(13) . . . . ?
Cl1 C7 C8 C9 -176.8(6) . . . . ?
C1 O1 C9 C8 -179.6(7) . . . . ?
C1 O1 C9 C4 -1.4(12) . . . . ?
C7 C8 C9 O1 -178.1(7) . . . . ?
C7 C8 C9 C4 3.7(13) . . . . ?
C5 C4 C9 O1 174.8(7) . . . . ?
C3 C4 C9 O1 -6.6(12) . . . . ?
C5 C4 C9 C8 -7.2(12) . . . . ?
C3 C4 C9 C8 171.5(8) . . . . ?
O4 S1 C11 C12 172.8(7) . . . . ?
O3 S1 C11 C12 42.8(8) . . . . ?
C2 S1 C11 C12 -70.3(8) . . . . ?
O4 S1 C11 C16 -4.5(8) . . . . ?
O3 S1 C11 C16 -134.5(7) . . . . ?
C2 S1 C11 C16 112.4(7) . . . . ?
C16 C11 C12 C13 -0.2(14) . . . . ?
S1 C11 C12 C13 -177.4(7) . . . . ?
C11 C12 C13 C14 1.1(15) . . . . ?
C12 C13 C14 C15 -1.0(16) . . . . ?
C13 C14 C15 C16 -0.1(15) . . . . ?
C12 C11 C16 C15 -0.8(14) . . . . ?
S1 C11 C16 C15 176.4(7) . . . . ?
C14 C15 C16 C11 0.9(14) . . . . ?
C2 C3 C31 C36 -105.3(11) . . . . ?
C4 C3 C31 C36 72.4(10) . . . . ?
C2 C3 C31 C32 77.7(12) . . . . ?
C4 C3 C31 C32 -104.7(10) . . . . ?
C36 C31 C32 C33 -0.7(14) . . . . ?
C3 C31 C32 C33 176.4(9) . . . . ?
C31 C32 C33 C34 0.7(15) . . . . ?
C32 C33 C34 C35 0.0(15) . . . . ?
C33 C34 C35 C36 -0.7(15) . . . . ?
C32 C31 C36 C35 0.0(14) . . . . ?
C3 C31 C36 C35 -177.1(9) . . . . ?
C34 C35 C36 C31 0.6(15) . . . . ?
C9A O1A C1A O2A 177.7(8) . . . . ?
C9A O1A C1A C2A -1.2(12) . . . . ?
O2A C1A C2A C3A -177.0(9) . . . . ?
O1A C1A C2A C3A 1.8(12) . . . . ?
O2A C1A C2A S1A 2.4(12) . . . . ?
O1A C1A C2A S1A -178.9(6) . . . . ?
O3A S1A C2A C3A -119.5(8) . . . . ?
O4A S1A C2A C3A 8.8(8) . . . . ?
C11A S1A C2A C3A 124.0(7) . . . . ?
O3A S1A C2A C1A 61.1(7) . . . . ?
O4A S1A C2A C1A -170.6(6) . . . . ?
C11A S1A C2A C1A -55.4(7) . . . . ?
C1A C2A C3A C4A -3.1(12) . . . . ?
S1A C2A C3A C4A 177.6(6) . . . . ?
C1A C2A C3A C31A 175.5(7) . . . . ?
S1A C2A C3A C31A -3.8(12) . . . . ?
C2A C3A C4A C9A 4.0(12) . . . . ?
C31A C3A C4A C9A -174.8(7) . . . . ?
C2A C3A C4A C5A -177.8(8) . . . . ?
C31A C3A C4A C5A 3.5(12) . . . . ?
C9A C4A C5A C6A 3.2(13) . . . . ?
C3A C4A C5A C6A -175.1(8) . . . . ?
C4A C5A C6A C7A -1.1(14) . . . . ?
C5A C6A C7A C8A -2.3(15) . . . . ?
C5A C6A C7A Cl1A 177.6(7) . . . . ?
C6A C7A C8A C9A 3.4(15) . . . . ?
Cl1A C7A C8A C9A -176.5(7) . . . . ?
C7A C8A C9A O1A 178.7(9) . . . . ?
C7A C8A C9A C4A -1.1(15) . . . . ?
C1A O1A C9A C8A -177.7(8) . . . . ?
C1A O1A C9A C4A 2.1(13) . . . . ?
C5A C4A C9A C8A -2.1(13) . . . . ?
C3A C4A C9A C8A 176.3(9) . . . . ?
C5A C4A C9A O1A 178.1(8) . . . . ?
C3A C4A C9A O1A -3.5(13) . . . . ?
O3A S1A C11A C16A 4.6(8) . . . . ?
O4A S1A C11A C16A -124.3(7) . . . . ?
C2A S1A C11A C16A 120.1(7) . . . . ?
O3A S1A C11A C12A 180.0(7) . . . . ?
O4A S1A C11A C12A 51.1(8) . . . . ?
C2A S1A C11A C12A -64.5(7) . . . . ?
C16A C11A C12A C13A -0.2(13) . . . . ?
S1A C11A C12A C13A -175.4(7) . . . . ?
C11A C12A C13A C14A 0.9(14) . . . . ?
C12A C13A C14A C15A -0.5(15) . . . . ?
C13A C14A C15A C16A -0.7(15) . . . . ?
C12A C11A C16A C15A -0.9(13) . . . . ?
S1A C11A C16A C15A 174.4(7) . . . . ?
C14A C15A C16A C11A 1.3(14) . . . . ?
C2A C3A C31A C32A 87.9(11) . . . . ?
C4A C3A C31A C32A -93.5(11) . . . . ?
C2A C3A C31A C36A -95.7(11) . . . . ?
C4A C3A C31A C36A 82.9(10) . . . . ?
C36A C31A C32A C33A 2.3(15) . . . . ?
C3A C31A C32A C33A 178.7(9) . . . . ?
C31A C32A C33A C34A -1.1(17) . . . . ?
C32A C33A C34A C35A -0.4(17) . . . . ?
C33A C34A C35A C36A 0.5(16) . . . . ?
C34A C35A C36A C31A 0.8(15) . . . . ?
C32A C31A C36A C35A -2.1(14) . . . . ?
C3A C31A C36A C35A -178.6(8) . . . . ?

_refine_diff_density_max         0.495
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.072

