# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1501891'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 O2 S'
_chemical_formula_sum            'C32 H22 O2 S'
_chemical_formula_weight         470.56

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   11.3812(9)
_cell_length_b                   9.0240(7)
_cell_length_c                   23.553(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.181(3)
_cell_angle_gamma                90.00
_cell_volume                     2380.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2247
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13366
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4304
_reflns_number_gt                2831
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.2146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93738(18) 0.6445(2) 0.07586(9) 0.0223(5) Uani 1 1 d . . .
C2 C 0.92727(19) 0.5366(3) 0.11426(9) 0.0241(5) Uani 1 1 d . . .
C3 C 1.01685(19) 0.5444(3) 0.16821(9) 0.0269(6) Uani 1 1 d . . .
C4 C 1.09522(19) 0.6633(3) 0.16889(10) 0.0266(6) Uani 1 1 d . . .
C5 C 1.1878(2) 0.6916(3) 0.21410(10) 0.0348(6) Uani 1 1 d . . .
H5 H 1.2400 0.7733 0.2132 0.042 Uiso 1 1 calc R . .
C6 C 1.2012(2) 0.5958(3) 0.26074(11) 0.0419(7) Uani 1 1 d . . .
H6 H 1.2644 0.6110 0.2924 0.050 Uiso 1 1 calc R . .
C7 C 1.1236(2) 0.4782(3) 0.26173(10) 0.0428(7) Uani 1 1 d . . .
H7 H 1.1338 0.4145 0.2943 0.051 Uiso 1 1 calc R . .
C8 C 1.0311(2) 0.4516(3) 0.21588(10) 0.0363(7) Uani 1 1 d . . .
H8 H 0.9782 0.3707 0.2172 0.044 Uiso 1 1 calc R . .
C9 C 0.87783(18) 0.6689(2) 0.01559(9) 0.0217(5) Uani 1 1 d . . .
C10 C 0.82713(19) 0.5511(2) -0.01889(9) 0.0252(5) Uani 1 1 d . . .
H10 H 0.8285 0.4541 -0.0031 0.030 Uiso 1 1 calc R . .
C11 C 0.77504(19) 0.5746(3) -0.07574(9) 0.0248(5) Uani 1 1 d . . .
H11 H 0.7403 0.4932 -0.0982 0.030 Uiso 1 1 calc R . .
C12 C 0.77193(19) 0.7147(3) -0.10113(9) 0.0232(5) Uani 1 1 d . . .
C13 C 0.82363(19) 0.8309(3) -0.06662(9) 0.0255(5) Uani 1 1 d . . .
H13 H 0.8224 0.9279 -0.0825 0.031 Uiso 1 1 calc R . .
C14 C 0.87677(19) 0.8084(2) -0.00977(9) 0.0244(5) Uani 1 1 d . . .
H14 H 0.9132 0.8895 0.0124 0.029 Uiso 1 1 calc R . .
C15 C 0.7186(2) 0.7381(3) -0.16266(10) 0.0264(6) Uani 1 1 d . . .
C16 C 0.6234(2) 0.6517(3) -0.18984(10) 0.0327(6) Uani 1 1 d . . .
H16 H 0.5925 0.5758 -0.1687 0.039 Uiso 1 1 calc R . .
C17 C 0.5733(2) 0.6750(3) -0.24719(11) 0.0430(7) Uani 1 1 d . . .
H17 H 0.5082 0.6155 -0.2650 0.052 Uiso 1 1 calc R . .
C18 C 0.6177(3) 0.7845(3) -0.27854(11) 0.0499(8) Uani 1 1 d . . .
H18 H 0.5832 0.8007 -0.3178 0.060 Uiso 1 1 calc R . .
C19 C 0.7121(3) 0.8699(3) -0.25256(11) 0.0482(8) Uani 1 1 d . . .
H19 H 0.7430 0.9450 -0.2741 0.058 Uiso 1 1 calc R . .
C20 C 0.7626(2) 0.8474(3) -0.19517(10) 0.0361(6) Uani 1 1 d . . .
H20 H 0.8279 0.9071 -0.1778 0.043 Uiso 1 1 calc R . .
C21 C 0.84050(19) 0.4120(3) 0.10581(9) 0.0238(5) Uani 1 1 d . . .
C22 C 0.88089(19) 0.2676(3) 0.10205(9) 0.0276(6) Uani 1 1 d . . .
H22 H 0.9640 0.2495 0.1053 0.033 Uiso 1 1 calc R . .
C23 C 0.80218(19) 0.1502(3) 0.09371(9) 0.0273(6) Uani 1 1 d . . .
H23 H 0.8319 0.0527 0.0904 0.033 Uiso 1 1 calc R . .
C24 C 0.67957(18) 0.1719(3) 0.08999(9) 0.0226(5) Uani 1 1 d . . .
C25 C 0.6397(2) 0.3168(3) 0.09440(9) 0.0258(6) Uani 1 1 d . . .
H25 H 0.5568 0.3347 0.0923 0.031 Uiso 1 1 calc R . .
C26 C 0.71828(19) 0.4353(3) 0.10173(9) 0.0263(6) Uani 1 1 d . . .
H26 H 0.6886 0.5331 0.1040 0.032 Uiso 1 1 calc R . .
C27 C 0.59842(19) 0.0418(3) 0.08289(9) 0.0239(5) Uani 1 1 d . . .
C28 C 0.6209(2) -0.0789(3) 0.04937(10) 0.0313(6) Uani 1 1 d . . .
H28 H 0.6890 -0.0775 0.0312 0.038 Uiso 1 1 calc R . .
C29 C 0.5457(2) -0.2005(3) 0.04218(11) 0.0373(7) Uani 1 1 d . . .
H29 H 0.5627 -0.2817 0.0192 0.045 Uiso 1 1 calc R . .
C30 C 0.4461(2) -0.2043(3) 0.06823(11) 0.0401(7) Uani 1 1 d . . .
H30 H 0.3938 -0.2872 0.0630 0.048 Uiso 1 1 calc R . .
C31 C 0.4236(2) -0.0861(3) 0.10195(11) 0.0362(7) Uani 1 1 d . . .
H31 H 0.3555 -0.0883 0.1201 0.043 Uiso 1 1 calc R . .
C32 C 0.49856(19) 0.0355(3) 0.10963(10) 0.0292(6) Uani 1 1 d . . .
H32 H 0.4820 0.1153 0.1333 0.035 Uiso 1 1 calc R . .
O1 O 1.14648(13) 0.77461(16) 0.07185(7) 0.0288(4) Uani 1 1 d . . .
O2 O 1.00657(14) 0.90966(17) 0.12083(7) 0.0344(4) Uani 1 1 d . . .
S1 S 1.05392(5) 0.76923(6) 0.10614(2) 0.02517(17) Uani 1 1 d . . .


_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
C1 C2 1.347(3) . ?
C1 C9 1.477(3) . ?
C1 S1 1.789(2) . ?
C2 C3 1.484(3) . ?
C2 C21 1.487(3) . ?
C3 C8 1.387(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.383(3) . ?
C4 S1 1.753(2) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.392(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 C15 1.484(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.395(3) . ?
C15 C16 1.395(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.390(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.379(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.396(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(3) . ?
C24 C27 1.485(3) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.394(3) . ?
C27 C32 1.395(3) . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.381(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
O1 S1 1.4371(15) . ?
O2 S1 1.4429(16) . ?

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
C2 C1 C9 132.4(2) . . ?
C2 C1 S1 109.39(17) . . ?
C9 C1 S1 118.09(17) . . ?
C1 C2 C3 114.4(2) . . ?
C1 C2 C21 126.2(2) . . ?
C3 C2 C21 119.33(19) . . ?
C8 C3 C4 118.2(2) . . ?
C8 C3 C2 129.0(2) . . ?
C4 C3 C2 112.8(2) . . ?
C5 C4 C3 123.3(2) . . ?
C5 C4 S1 127.09(19) . . ?
C3 C4 S1 109.54(16) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 119.3(2) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C14 C9 C10 117.8(2) . . ?
C14 C9 C1 121.0(2) . . ?
C10 C9 C1 121.1(2) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.9(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 117.1(2) . . ?
C13 C12 C15 121.4(2) . . ?
C11 C12 C15 121.5(2) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C9 121.1(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C20 C15 C16 117.9(2) . . ?
C20 C15 C12 120.8(2) . . ?
C16 C15 C12 121.3(2) . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C22 C21 C26 118.3(2) . . ?
C22 C21 C2 119.90(19) . . ?
C26 C21 C2 121.8(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 121.2(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 117.5(2) . . ?
C25 C24 C27 123.09(19) . . ?
C23 C24 C27 119.4(2) . . ?
C26 C25 C24 121.5(2) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C28 C27 C32 118.0(2) . . ?
C28 C27 C24 120.6(2) . . ?
C32 C27 C24 121.4(2) . . ?
C29 C28 C27 121.2(2) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 119.1(2) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C32 121.1(2) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C31 C32 C27 120.4(2) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
O1 S1 O2 116.55(10) . . ?
O1 S1 C4 112.23(10) . . ?
O2 S1 C4 109.41(10) . . ?
O1 S1 C1 111.26(10) . . ?
O2 S1 C1 111.49(10) . . ?
C4 S1 C1 93.58(11) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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 1511289'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 F2 O2 S'
_chemical_formula_sum            'C20 H12 F2 O2 S'
_chemical_formula_weight         354.36

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   10.3524(5)
_cell_length_b                   10.3346(6)
_cell_length_c                   15.3392(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.291(2)
_cell_angle_gamma                90.00
_cell_volume                     1639.80(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4604
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6710
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8942
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2869
_reflns_number_gt                2293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.7047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2869
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2066(2) 0.9210(2) 0.05562(15) 0.0195(5) Uani 1 1 d . . .
C2 C 0.2648(2) 0.9533(2) -0.01848(14) 0.0197(5) Uani 1 1 d . . .
C3 C 0.2675(2) 1.0958(2) -0.03561(15) 0.0226(5) Uani 1 1 d . . .
C4 C 0.2081(2) 1.1676(2) 0.02876(14) 0.0233(5) Uani 1 1 d . . .
C5 C 0.1976(3) 1.3009(2) 0.02690(16) 0.0317(6) Uani 1 1 d . . .
H5 H 0.1552 1.3469 0.0711 0.038 Uiso 1 1 calc R . .
C6 C 0.2519(3) 1.3650(3) -0.04283(18) 0.0405(7) Uani 1 1 d . . .
H6 H 0.2489 1.4567 -0.0456 0.049 Uiso 1 1 calc R . .
C7 C 0.3100(3) 1.2964(3) -0.10767(17) 0.0372(7) Uani 1 1 d . . .
H7 H 0.3452 1.3418 -0.1551 0.045 Uiso 1 1 calc R . .
C8 C 0.3182(2) 1.1615(2) -0.10511(16) 0.0294(6) Uani 1 1 d . . .
H8 H 0.3580 1.1155 -0.1504 0.035 Uiso 1 1 calc R . .
C9 C 0.1646(3) 0.5631(2) 0.18538(16) 0.0346(6) Uani 1 1 d . . .
C10 C 0.2815(3) 0.5921(2) 0.15034(17) 0.0346(6) Uani 1 1 d . . .
H10 H 0.3520 0.5334 0.1557 0.041 Uiso 1 1 calc R . .
C11 C 0.2941(2) 0.7091(2) 0.10709(16) 0.0280(6) Uani 1 1 d . . .
H11 H 0.3741 0.7308 0.0826 0.034 Uiso 1 1 calc R . .
C12 C 0.1905(2) 0.7951(2) 0.09922(14) 0.0216(5) Uani 1 1 d . . .
C13 C 0.0741(2) 0.7619(2) 0.13605(15) 0.0279(6) Uani 1 1 d . . .
H13 H 0.0030 0.8199 0.1314 0.034 Uiso 1 1 calc R . .
C14 C 0.0607(3) 0.6452(3) 0.17937(17) 0.0354(6) Uani 1 1 d . . .
H14 H -0.0188 0.6226 0.2043 0.042 Uiso 1 1 calc R . .
C15 C 0.4165(2) 0.6780(2) -0.19121(15) 0.0252(5) Uani 1 1 d . . .
C16 C 0.4958(2) 0.7766(2) -0.16229(16) 0.0283(6) Uani 1 1 d . . .
H16 H 0.5828 0.7820 -0.1796 0.034 Uiso 1 1 calc R . .
C17 C 0.4453(2) 0.8682(2) -0.10690(15) 0.0262(5) Uani 1 1 d . . .
H17 H 0.4977 0.9386 -0.0871 0.031 Uiso 1 1 calc R . .
C18 C 0.3190(2) 0.8583(2) -0.08012(14) 0.0200(5) Uani 1 1 d . . .
C19 C 0.2413(2) 0.7569(2) -0.11187(14) 0.0209(5) Uani 1 1 d . . .
H19 H 0.1544 0.7503 -0.0947 0.025 Uiso 1 1 calc R . .
C20 C 0.2899(2) 0.6658(2) -0.16827(15) 0.0228(5) Uani 1 1 d . . .
H20 H 0.2374 0.5969 -0.1904 0.027 Uiso 1 1 calc R . .
F1 F 0.15246(19) 0.44742(15) 0.22703(11) 0.0545(5) Uani 1 1 d . . .
F2 F 0.46478(14) 0.58739(14) -0.24632(10) 0.0386(4) Uani 1 1 d . . .
O1 O 0.21418(16) 1.08075(15) 0.19120(10) 0.0270(4) Uani 1 1 d . . .
O2 O 0.00922(15) 1.06474(16) 0.10608(11) 0.0307(4) Uani 1 1 d . . .
S1 S 0.14791(5) 1.06218(5) 0.10759(4) 0.02086(19) Uani 1 1 d . . .


_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
C1 C2 1.350(3) . ?
C1 C12 1.476(3) . ?
C1 S1 1.781(2) . ?
C2 C18 1.488(3) . ?
C2 C3 1.497(3) . ?
C3 C8 1.385(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.382(3) . ?
C4 S1 1.760(2) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 F1 1.363(3) . ?
C9 C14 1.370(4) . ?
C9 C10 1.377(4) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 F2 1.369(3) . ?
C15 C16 1.371(3) . ?
C15 C20 1.376(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(3) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O1 S1 1.4429(17) . ?
O2 S1 1.4352(17) . ?

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
C2 C1 C12 131.4(2) . . ?
C2 C1 S1 110.27(17) . . ?
C12 C1 S1 118.23(16) . . ?
C1 C2 C18 124.3(2) . . ?
C1 C2 C3 113.8(2) . . ?
C18 C2 C3 121.85(19) . . ?
C8 C3 C4 118.4(2) . . ?
C8 C3 C2 128.9(2) . . ?
C4 C3 C2 112.7(2) . . ?
C5 C4 C3 123.4(2) . . ?
C5 C4 S1 126.98(19) . . ?
C3 C4 S1 109.59(17) . . ?
C4 C5 C6 117.1(2) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.4(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C3 C8 C7 119.1(2) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
F1 C9 C14 119.2(2) . . ?
F1 C9 C10 118.2(2) . . ?
C14 C9 C10 122.6(2) . . ?
C9 C10 C11 118.5(2) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 C1 121.0(2) . . ?
C11 C12 C1 120.1(2) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C9 C14 C13 118.5(2) . . ?
C9 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F2 C15 C16 118.6(2) . . ?
F2 C15 C20 118.0(2) . . ?
C16 C15 C20 123.3(2) . . ?
C15 C16 C17 118.0(2) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 C2 121.4(2) . . ?
C19 C18 C2 119.36(19) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C15 C20 C19 118.1(2) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
O2 S1 O1 116.85(10) . . ?
O2 S1 C4 111.02(11) . . ?
O1 S1 C4 111.08(10) . . ?
O2 S1 C1 111.53(10) . . ?
O1 S1 C1 110.38(10) . . ?
C4 S1 C1 93.61(11) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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 1501892'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 O4 S'
_chemical_formula_sum            'C22 H18 O4 S'
_chemical_formula_weight         378.42

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6225(9)
_cell_length_b                   10.5635(9)
_cell_length_c                   10.9316(9)
_cell_angle_alpha                63.981(2)
_cell_angle_beta                 64.608(3)
_cell_angle_gamma                78.743(3)
_cell_volume                     902.05(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    1888
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      24.94

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5838
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8404
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.34
_reflns_number_total             3248
_reflns_number_gt                2046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0303P)²+0.3687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3248
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2754(3) 0.6135(3) 0.5983(3) 0.0218(7) Uani 1 1 d . . .
C2 C 0.2838(3) 0.5486(3) 0.7328(3) 0.0228(7) Uani 1 1 d . . .
C3 C 0.3289(3) 0.6419(3) 0.7780(3) 0.0242(7) Uani 1 1 d . . .
C4 C 0.3508(3) 0.7812(3) 0.6749(3) 0.0242(7) Uani 1 1 d . . .
C5 C 0.3879(4) 0.8863(3) 0.6975(3) 0.0303(8) Uani 1 1 d . . .
H5 H 0.3997 0.9809 0.6264 0.036 Uiso 1 1 calc R . .
C6 C 0.4076(4) 0.8499(4) 0.8273(3) 0.0355(9) Uani 1 1 d . . .
H6 H 0.4347 0.9199 0.8455 0.043 Uiso 1 1 calc R . .
C7 C 0.3879(4) 0.7122(4) 0.9304(3) 0.0355(9) Uani 1 1 d . . .
H7 H 0.4020 0.6888 1.0187 0.043 Uiso 1 1 calc R . .
C8 C 0.3479(4) 0.6071(3) 0.9079(3) 0.0301(8) Uani 1 1 d . . .
H8 H 0.3338 0.5130 0.9803 0.036 Uiso 1 1 calc R . .
C9 C 0.1923(4) 0.4456(3) 0.3452(3) 0.0254(8) Uani 1 1 d . . .
C10 C 0.2557(4) 0.3612(3) 0.4475(3) 0.0267(8) Uani 1 1 d . . .
H10 H 0.2804 0.2654 0.4623 0.032 Uiso 1 1 calc R . .
C11 C 0.2829(4) 0.4173(3) 0.5282(3) 0.0257(8) Uani 1 1 d . . .
H11 H 0.3267 0.3589 0.5981 0.031 Uiso 1 1 calc R . .
C12 C 0.2477(3) 0.5568(3) 0.5097(3) 0.0225(7) Uani 1 1 d . . .
C13 C 0.1900(4) 0.6416(3) 0.4018(3) 0.0278(8) Uani 1 1 d . . .
H13 H 0.1695 0.7385 0.3836 0.033 Uiso 1 1 calc R . .
C14 C 0.1622(4) 0.5867(3) 0.3212(3) 0.0298(8) Uani 1 1 d . . .
H14 H 0.1221 0.6459 0.2486 0.036 Uiso 1 1 calc R . .
C15 C 0.1681(4) 0.2530(3) 0.2961(4) 0.0391(9) Uani 1 1 d . . .
H15A H 0.2756 0.2223 0.2757 0.059 Uiso 1 1 calc R . .
H15B H 0.1313 0.2345 0.2347 0.059 Uiso 1 1 calc R . .
H15C H 0.1051 0.2010 0.4007 0.059 Uiso 1 1 calc R . .
C16 C 0.1599(4) 0.1220(3) 1.0336(3) 0.0223(7) Uani 1 1 d . . .
C17 C 0.3128(4) 0.1612(3) 0.9617(3) 0.0277(8) Uani 1 1 d . . .
H17 H 0.3900 0.0928 0.9795 0.033 Uiso 1 1 calc R . .
C18 C 0.3543(4) 0.2984(3) 0.8644(3) 0.0284(8) Uani 1 1 d . . .
H18 H 0.4597 0.3240 0.8162 0.034 Uiso 1 1 calc R . .
C19 C 0.2427(4) 0.3996(3) 0.8366(3) 0.0202(7) Uani 1 1 d . . .
C20 C 0.0892(4) 0.3597(3) 0.9096(3) 0.0246(8) Uani 1 1 d . . .
H20 H 0.0118 0.4278 0.8917 0.029 Uiso 1 1 calc R . .
C21 C 0.0474(4) 0.2218(3) 1.0081(3) 0.0245(8) Uani 1 1 d . . .
H21 H -0.0580 0.1960 1.0579 0.029 Uiso 1 1 calc R . .
C22 C -0.0264(4) -0.0536(3) 1.2187(3) 0.0374(9) Uani 1 1 d . . .
H22A H -0.0691 0.0006 1.2804 0.056 Uiso 1 1 calc R . .
H22B H -0.0335 -0.1545 1.2820 0.056 Uiso 1 1 calc R . .
H22C H -0.0845 -0.0320 1.1569 0.056 Uiso 1 1 calc R . .
O1 O 0.4577(3) 0.8296(2) 0.3911(2) 0.0320(6) Uani 1 1 d . . .
O2 O 0.1855(3) 0.8844(2) 0.5131(2) 0.0346(6) Uani 1 1 d . . .
O3 O 0.1567(3) 0.4006(2) 0.2629(2) 0.0357(6) Uani 1 1 d . . .
O4 O 0.1309(3) -0.0170(2) 1.1266(2) 0.0345(6) Uani 1 1 d . . .
S1 S 0.31812(10) 0.79606(8) 0.52261(9) 0.0254(2) Uani 1 1 d . . .


_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
C1 C2 1.354(4) . ?
C1 C12 1.471(4) . ?
C1 S1 1.786(3) . ?
C2 C3 1.477(4) . ?
C2 C19 1.487(4) . ?
C3 C8 1.387(4) . ?
C3 C4 1.393(4) . ?
C4 C5 1.375(4) . ?
C4 S1 1.760(3) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 O3 1.363(3) . ?
C9 C10 1.384(4) . ?
C9 C14 1.389(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(4) . ?
C13 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O3 1.430(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O4 1.369(3) . ?
C16 C17 1.384(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(4) . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O4 1.426(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1 S1 1.442(2) . ?
O2 S1 1.440(2) . ?

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
C2 C1 C12 131.0(3) . . ?
C2 C1 S1 109.5(2) . . ?
C12 C1 S1 119.4(2) . . ?
C1 C2 C3 114.2(3) . . ?
C1 C2 C19 125.8(3) . . ?
C3 C2 C19 119.9(2) . . ?
C8 C3 C4 118.6(3) . . ?
C8 C3 C2 127.9(3) . . ?
C4 C3 C2 113.4(3) . . ?
C5 C4 C3 122.9(3) . . ?
C5 C4 S1 127.9(2) . . ?
C3 C4 S1 109.2(2) . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 118.8(3) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O3 C9 C10 124.6(3) . . ?
O3 C9 C14 116.0(3) . . ?
C10 C9 C14 119.5(3) . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 117.9(3) . . ?
C11 C12 C1 120.7(2) . . ?
C13 C12 C1 121.4(3) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 C17 116.2(3) . . ?
O4 C16 C21 124.2(3) . . ?
C17 C16 C21 119.6(3) . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 C2 119.7(3) . . ?
C18 C19 C2 121.6(3) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C16 C21 C20 119.7(3) . . ?
C16 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 O3 C15 118.0(2) . . ?
C16 O4 C22 116.3(2) . . ?
O2 S1 O1 117.40(13) . . ?
O2 S1 C4 109.85(14) . . ?
O1 S1 C4 111.35(13) . . ?
O2 S1 C1 112.00(14) . . ?
O1 S1 C1 110.08(14) . . ?
C4 S1 C1 93.67(13) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.337
_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_1
_database_code_depnum_ccdc_archive 'CCDC 1501899'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 O2 S'
_chemical_formula_sum            'C22 H18 O2 S'
_chemical_formula_weight         346.42

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn  '

loop_
_symmetry_equiv_pos_as_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                   9.9496(11)
_cell_length_b                   12.5896(12)
_cell_length_c                   14.3507(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.202(4)
_cell_angle_gamma                90.00
_cell_volume                     1774.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2333
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      24.89

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11820
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.39
_reflns_number_total             3237
_reflns_number_gt                2153
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0281P)²+1.1052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     293
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.007
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3075(2) 0.11518(16) 0.83939(16) 0.0278(5) Uani 1 1 d . A .
C2 C 0.3761(2) 0.18733(18) 0.89658(16) 0.0316(6) Uani 1 1 d D . .
C3 C 0.3078(2) 0.21753(18) 0.97763(16) 0.0314(6) Uani 1 1 d . A .
C4 C 0.1832(2) 0.16786(18) 0.97682(16) 0.0316(6) Uani 1 1 d . . .
C5 C 0.1033(3) 0.1825(2) 1.04576(17) 0.0407(6) Uani 1 1 d . A .
H5A H 0.0183 0.1473 1.0431 0.049 Uiso 1 1 calc R . .
C6 C 0.1525(3) 0.2509(2) 1.11937(18) 0.0466(7) Uani 1 1 d . . .
H6A H 0.0997 0.2641 1.1678 0.056 Uiso 1 1 calc R A .
C7 C 0.2769(3) 0.2998(2) 1.12273(18) 0.0482(7) Uani 1 1 d . A .
H7A H 0.3097 0.3450 1.1744 0.058 Uiso 1 1 calc R . .
C8 C 0.3555(3) 0.2843(2) 1.05202(18) 0.0443(7) Uani 1 1 d . . .
H8A H 0.4407 0.3191 1.0548 0.053 Uiso 1 1 calc R A .
C9 C 0.3395(2) 0.05993(18) 0.75489(16) 0.0317(6) Uani 1 1 d . . .
C10 C 0.3215(2) 0.1068(2) 0.66687(18) 0.0408(6) Uani 1 1 d . A .
C11 C 0.3556(3) 0.0465(2) 0.5898(2) 0.0483(7) Uani 1 1 d . . .
H11A H 0.3450 0.0765 0.5283 0.058 Uiso 1 1 calc R A .
C12 C 0.4035(3) -0.0547(2) 0.6049(2) 0.0493(7) Uani 1 1 d . A .
H12A H 0.4269 -0.0936 0.5531 0.059 Uiso 1 1 calc R . .
C13 C 0.4190(3) -0.1022(2) 0.6916(2) 0.0534(8) Uani 1 1 d . . .
H13A H 0.4512 -0.1732 0.6996 0.064 Uiso 1 1 calc R A .
C14 C 0.3874(3) -0.0456(2) 0.7667(2) 0.0448(7) Uani 1 1 d . A .
H14A H 0.3978 -0.0777 0.8273 0.054 Uiso 1 1 calc R . .
C15 C 0.2680(3) 0.2159(2) 0.65150(19) 0.0542(8) Uani 1 1 d . . .
H15A H 0.1816 0.2219 0.6757 0.081 Uiso 1 1 calc R A .
H15B H 0.2531 0.2319 0.5838 0.081 Uiso 1 1 calc R . .
H15C H 0.3339 0.2664 0.6848 0.081 Uiso 1 1 calc R . .
C16 C 0.4972(6) 0.2510(4) 0.8755(3) 0.0298(13) Uani 0.618(4) 1 d PDU A 1
C17 C 0.6244(4) 0.2029(4) 0.8791(3) 0.0345(10) Uani 0.618(4) 1 d PDU A 1
C18 C 0.7322(6) 0.2680(6) 0.8599(5) 0.0453(14) Uani 0.618(4) 1 d PDU A 1
H18A H 0.8203 0.2378 0.8626 0.054 Uiso 0.618(4) 1 calc PR A 1
C19 C 0.7136(5) 0.3730(4) 0.8377(4) 0.0458(13) Uani 0.618(4) 1 d PDU A 1
H19A H 0.7882 0.4147 0.8250 0.055 Uiso 0.618(4) 1 calc PR A 1
C20 C 0.5881(4) 0.4181(4) 0.8336(3) 0.0461(11) Uani 0.618(4) 1 d PDU A 1
H20A H 0.5749 0.4910 0.8176 0.055 Uiso 0.618(4) 1 calc PR A 1
C21 C 0.4811(6) 0.3577(4) 0.8527(5) 0.0386(13) Uani 0.618(4) 1 d PDU A 1
H21A H 0.3941 0.3896 0.8502 0.046 Uiso 0.618(4) 1 calc PR A 1
C22 C 0.6494(7) 0.0886(5) 0.9027(6) 0.0561(18) Uani 0.618(4) 1 d PDU A 1
H22A H 0.5864 0.0649 0.9443 0.084 Uiso 0.618(4) 1 calc PR A 1
H22B H 0.7433 0.0794 0.9347 0.084 Uiso 0.618(4) 1 calc PR A 1
H22C H 0.6350 0.0465 0.8445 0.084 Uiso 0.618(4) 1 calc PR A 1
C16' C 0.5214(9) 0.2109(6) 0.8927(5) 0.0293(19) Uani 0.382(4) 1 d PDU A 2
C17' C 0.5559(7) 0.3151(6) 0.8784(5) 0.0345(15) Uani 0.382(4) 1 d PDU A 2
C18' C 0.6924(8) 0.3350(8) 0.8667(6) 0.0397(17) Uani 0.382(4) 1 d PDU A 2
H18B H 0.7194 0.4051 0.8536 0.048 Uiso 0.382(4) 1 calc PR A 2
C19' C 0.7851(10) 0.2547(9) 0.8740(8) 0.043(2) Uani 0.382(4) 1 d PDU A 2
H19B H 0.8762 0.2704 0.8667 0.052 Uiso 0.382(4) 1 calc PR A 2
C20' C 0.7513(6) 0.1525(6) 0.8915(4) 0.0415(16) Uani 0.382(4) 1 d PDU A 2
H20B H 0.8171 0.0973 0.8952 0.050 Uiso 0.382(4) 1 calc PR A 2
C21' C 0.6195(9) 0.1314(8) 0.9035(7) 0.035(2) Uani 0.382(4) 1 d PDU A 2
H21B H 0.5953 0.0616 0.9195 0.042 Uiso 0.382(4) 1 calc PR A 2
C22' C 0.4558(10) 0.4037(7) 0.8682(8) 0.044(2) Uani 0.382(4) 1 d PDU A 2
H22D H 0.3700 0.3797 0.8308 0.066 Uiso 0.382(4) 1 calc PR A 2
H22E H 0.4919 0.4636 0.8361 0.066 Uiso 0.382(4) 1 calc PR A 2
H22F H 0.4395 0.4263 0.9307 0.066 Uiso 0.382(4) 1 calc PR A 2
O1 O 0.14478(18) -0.02489(12) 0.90346(12) 0.0468(5) Uani 1 1 d . . .
O2 O 0.03878(16) 0.12400(13) 0.80972(11) 0.0402(4) Uani 1 1 d . . .
S1 S 0.15023(6) 0.08452(5) 0.87709(4) 0.03216(17) Uani 1 1 d . A .


_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
C1 C2 1.336(3) . ?
C1 C9 1.476(3) . ?
C1 S1 1.778(2) . ?
C2 C16' 1.486(10) . ?
C2 C3 1.487(3) . ?
C2 C16 1.517(6) . ?
C3 C8 1.381(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.377(3) . ?
C4 S1 1.763(2) . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.377(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.380(3) . ?
C9 C14 1.413(3) . ?
C10 C11 1.427(3) . ?
C10 C15 1.476(4) . ?
C11 C12 1.365(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.367(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.369(4) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.386(7) . ?
C16 C17 1.397(6) . ?
C17 C18 1.411(8) . ?
C17 C22 1.489(7) . ?
C18 C19 1.366(7) . ?
C18 H18A 0.9500 . ?
C19 C20 1.365(7) . ?
C19 H19A 0.9500 . ?
C20 C21 1.372(6) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C16' C17' 1.379(9) . ?
C16' C21' 1.389(10) . ?
C17' C18' 1.417(10) . ?
C17' C22' 1.488(10) . ?
C18' C19' 1.361(11) . ?
C18' H18B 0.9500 . ?
C19' C20' 1.363(12) . ?
C19' H19B 0.9500 . ?
C20' C21' 1.376(11) . ?
C20' H20B 0.9500 . ?
C21' H21B 0.9500 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?
O1 S1 1.4318(16) . ?
O2 S1 1.4382(17) . ?

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
C2 C1 C9 132.0(2) . . ?
C2 C1 S1 110.40(17) . . ?
C9 C1 S1 117.60(16) . . ?
C1 C2 C16' 121.1(3) . . ?
C1 C2 C3 113.7(2) . . ?
C16' C2 C3 123.2(3) . . ?
C1 C2 C16 125.5(3) . . ?
C16' C2 C16 22.8(3) . . ?
C3 C2 C16 119.8(3) . . ?
C8 C3 C4 118.4(2) . . ?
C8 C3 C2 128.1(2) . . ?
C4 C3 C2 113.4(2) . . ?
C5 C4 C3 123.5(2) . . ?
C5 C4 S1 127.55(19) . . ?
C3 C4 S1 108.96(17) . . ?
C4 C5 C6 117.1(2) . . ?
C4 C5 H5A 121.4 . . ?
C6 C5 H5A 121.4 . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C3 C8 C7 119.1(2) . . ?
C3 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C10 C9 C14 120.3(2) . . ?
C10 C9 C1 122.5(2) . . ?
C14 C9 C1 117.2(2) . . ?
C9 C10 C11 118.0(2) . . ?
C9 C10 C15 121.7(2) . . ?
C11 C10 C15 120.3(2) . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 122.6(3) . . ?
C11 C12 H12A 118.7 . . ?
C13 C12 H12A 118.7 . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13A 120.6 . . ?
C14 C13 H13A 120.6 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14A 119.7 . . ?
C9 C14 H14A 119.7 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 119.9(5) . . ?
C21 C16 C2 119.6(4) . . ?
C17 C16 C2 120.5(4) . . ?
C16 C17 C18 117.0(5) . . ?
C16 C17 C22 123.0(5) . . ?
C18 C17 C22 120.0(5) . . ?
C19 C18 C17 121.9(6) . . ?
C19 C18 H18A 119.0 . . ?
C17 C18 H18A 119.0 . . ?
C20 C19 C18 120.1(5) . . ?
C20 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
C19 C20 C21 119.7(5) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C16 121.4(6) . . ?
C20 C21 H21A 119.3 . . ?
C16 C21 H21A 119.3 . . ?
C17' C16' C21' 121.0(9) . . ?
C17' C16' C2 117.5(6) . . ?
C21' C16' C2 121.5(7) . . ?
C16' C17' C18' 116.8(7) . . ?
C16' C17' C22' 123.3(7) . . ?
C18' C17' C22' 119.7(8) . . ?
C19' C18' C17' 120.7(8) . . ?
C19' C18' H18B 119.7 . . ?
C17' C18' H18B 119.7 . . ?
C18' C19' C20' 122.1(9) . . ?
C18' C19' H19B 119.0 . . ?
C20' C19' H19B 119.0 . . ?
C19' C20' C21' 118.2(8) . . ?
C19' C20' H20B 120.9 . . ?
C21' C20' H20B 120.9 . . ?
C20' C21' C16' 120.9(10) . . ?
C20' C21' H21B 119.5 . . ?
C16' C21' H21B 119.5 . . ?
C17' C22' H22D 109.5 . . ?
C17' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C17' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
O1 S1 O2 116.90(11) . . ?
O1 S1 C4 111.59(11) . . ?
O2 S1 C4 111.30(11) . . ?
O1 S1 C1 111.20(10) . . ?
O2 S1 C1 109.99(10) . . ?
C4 S1 C1 93.41(11) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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 1501903'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O2 S'
_chemical_formula_sum            'C20 H14 O2 S'
_chemical_formula_weight         318.37

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Cc   '
_symmetry_space_group_name_Hall  'C -2yc'

loop_
_symmetry_equiv_pos_as_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                   8.7763(9)
_cell_length_b                   18.341(2)
_cell_length_c                   19.844(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.092(4)
_cell_angle_gamma                90.00
_cell_volume                     3144.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    2324
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.30

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9091
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0844
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.39
_reflns_number_total             5181
_reflns_number_gt                3807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0313P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_number_reflns         5181
_refine_ls_number_parameters     415
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.4966(4) 0.02194(18) 0.04528(18) 0.0234(8) Uani 1 1 d . . .
C2A C 0.3472(4) 0.00997(19) 0.01786(18) 0.0212(8) Uani 1 1 d . . .
C3A C 0.2472(4) 0.07493(19) 0.01887(19) 0.0230(9) Uani 1 1 d . . .
C4A C 0.3256(4) 0.1369(2) 0.04678(18) 0.0254(9) Uani 1 1 d . . .
C5A C 0.2557(5) 0.2016(2) 0.0578(2) 0.0327(10) Uani 1 1 d . . .
H5A H 0.3141 0.2420 0.0782 0.039 Uiso 1 1 calc R . .
C6A C 0.0960(5) 0.2059(2) 0.0381(2) 0.0364(10) Uani 1 1 d . . .
H6A H 0.0434 0.2501 0.0439 0.044 Uiso 1 1 calc R . .
C7A C 0.0138(4) 0.1457(2) 0.0099(2) 0.0356(10) Uani 1 1 d . . .
H7A H -0.0954 0.1491 -0.0033 0.043 Uiso 1 1 calc R . .
C8A C 0.0873(4) 0.0804(2) 0.0006(2) 0.0313(10) Uani 1 1 d . . .
H8A H 0.0283 0.0395 -0.0182 0.038 Uiso 1 1 calc R . .
C9A C 0.6345(4) -0.02495(18) 0.05749(19) 0.0226(8) Uani 1 1 d . . .
C10A C 0.6934(4) -0.0473(2) 0.1239(2) 0.0374(11) Uani 1 1 d . . .
H10A H 0.6394 -0.0353 0.1599 0.045 Uiso 1 1 calc R . .
C11A C 0.8298(5) -0.0870(2) 0.1383(2) 0.0445(12) Uani 1 1 d . . .
H11A H 0.8695 -0.1012 0.1840 0.053 Uiso 1 1 calc R . .
C12A C 0.9068(5) -0.1055(2) 0.0869(3) 0.0463(12) Uani 1 1 d . . .
H12A H 1.0005 -0.1325 0.0967 0.056 Uiso 1 1 calc R . .
C13A C 0.8483(5) -0.0850(2) 0.0204(3) 0.0472(12) Uani 1 1 d . . .
H13A H 0.9013 -0.0984 -0.0155 0.057 Uiso 1 1 calc R . .
C14A C 0.7129(5) -0.0449(2) 0.0059(2) 0.0369(10) Uani 1 1 d . . .
H14A H 0.6736 -0.0309 -0.0400 0.044 Uiso 1 1 calc R . .
C15A C 0.2834(4) -0.06103(19) -0.00753(19) 0.0219(9) Uani 1 1 d . . .
C16A C 0.3018(4) -0.1224(2) 0.0344(2) 0.0273(9) Uani 1 1 d . . .
H16A H 0.3583 -0.1187 0.0797 0.033 Uiso 1 1 calc R . .
C17A C 0.2391(4) -0.18841(19) 0.0110(2) 0.0349(10) Uani 1 1 d . . .
H17A H 0.2515 -0.2298 0.0402 0.042 Uiso 1 1 calc R . .
C18A C 0.1578(4) -0.1945(2) -0.0554(2) 0.0359(11) Uani 1 1 d . . .
H18A H 0.1152 -0.2402 -0.0717 0.043 Uiso 1 1 calc R . .
C19A C 0.1390(4) -0.1345(2) -0.0974(2) 0.0349(10) Uani 1 1 d . . .
H19A H 0.0834 -0.1389 -0.1428 0.042 Uiso 1 1 calc R . .
C20A C 0.2008(4) -0.0674(2) -0.0741(2) 0.0294(10) Uani 1 1 d . . .
H20A H 0.1868 -0.0261 -0.1034 0.035 Uiso 1 1 calc R . .
C1B C 0.4166(4) 0.93006(19) 0.77220(19) 0.0246(9) Uani 1 1 d . . .
C2B C 0.4002(4) 0.85796(19) 0.77155(19) 0.0246(9) Uani 1 1 d . . .
C3B C 0.2427(4) 0.83233(19) 0.73943(19) 0.0250(9) Uani 1 1 d . . .
C4B C 0.1447(4) 0.8884(2) 0.71212(19) 0.0254(9) Uani 1 1 d . . .
C5B C -0.0086(4) 0.8783(2) 0.68597(19) 0.0322(10) Uani 1 1 d . . .
H5B H -0.0729 0.9181 0.6685 0.039 Uiso 1 1 calc R . .
C6B C -0.0670(4) 0.8081(2) 0.6858(2) 0.0381(11) Uani 1 1 d . . .
H6B H -0.1729 0.7992 0.6678 0.046 Uiso 1 1 calc R . .
C7B C 0.0282(4) 0.7508(2) 0.7119(2) 0.0392(11) Uani 1 1 d . . .
H7B H -0.0133 0.7029 0.7112 0.047 Uiso 1 1 calc R . .
C8B C 0.1826(4) 0.7621(2) 0.7388(2) 0.0317(10) Uani 1 1 d . . .
H8B H 0.2468 0.7224 0.7566 0.038 Uiso 1 1 calc R . .
C9B C 0.5508(4) 0.9779(2) 0.79680(18) 0.0249(9) Uani 1 1 d . . .
C10B C 0.5305(5) 1.0444(2) 0.8279(2) 0.0365(10) Uani 1 1 d . . .
H10B H 0.4300 1.0586 0.8345 0.044 Uiso 1 1 calc R . .
C11B C 0.6548(5) 1.0899(2) 0.8493(2) 0.0438(12) Uani 1 1 d . . .
H11B H 0.6391 1.1351 0.8704 0.053 Uiso 1 1 calc R . .
C12B C 0.8010(5) 1.0703(2) 0.8404(2) 0.0397(11) Uani 1 1 d . . .
H12B H 0.8865 1.1017 0.8550 0.048 Uiso 1 1 calc R . .
C13B C 0.8214(4) 1.0046(2) 0.80992(19) 0.0369(11) Uani 1 1 d . . .
H13B H 0.9224 0.9908 0.8038 0.044 Uiso 1 1 calc R . .
C14B C 0.6996(4) 0.9582(2) 0.7880(2) 0.0301(10) Uani 1 1 d . . .
H14B H 0.7167 0.9131 0.7670 0.036 Uiso 1 1 calc R . .
C15B C 0.5212(4) 0.8042(2) 0.8002(2) 0.0255(9) Uani 1 1 d . . .
C16B C 0.6016(4) 0.8123(2) 0.8659(2) 0.0375(11) Uani 1 1 d . . .
H16B H 0.5759 0.8509 0.8938 0.045 Uiso 1 1 calc R . .
C17B C 0.7201(5) 0.7642(2) 0.8918(2) 0.0467(12) Uani 1 1 d . . .
H17B H 0.7769 0.7708 0.9367 0.056 Uiso 1 1 calc R . .
C18B C 0.7548(5) 0.7074(3) 0.8525(3) 0.0520(13) Uani 1 1 d . . .
H18B H 0.8349 0.6742 0.8704 0.062 Uiso 1 1 calc R . .
C19B C 0.6738(5) 0.6980(2) 0.7866(3) 0.0466(12) Uani 1 1 d . . .
H19B H 0.6977 0.6583 0.7596 0.056 Uiso 1 1 calc R . .
C20B C 0.5572(4) 0.7469(2) 0.7601(2) 0.0343(10) Uani 1 1 d . . .
H20B H 0.5025 0.7411 0.7147 0.041 Uiso 1 1 calc R . .
O1A O 0.5802(3) 0.12490(14) 0.14023(13) 0.0360(7) Uani 1 1 d . . .
O2A O 0.6107(3) 0.15017(14) 0.02176(14) 0.0407(7) Uani 1 1 d . . .
O1B O 0.1712(3) 1.01695(13) 0.77222(13) 0.0310(6) Uani 1 1 d . . .
O2B O 0.2764(3) 1.00607(14) 0.66562(13) 0.0348(7) Uani 1 1 d . . .
S1A S 0.52432(9) 0.11532(5) 0.06821(5) 0.0265(2) Uani 1 1 d . . .
S1B S 0.24478(10) 0.97226(5) 0.72731(5) 0.0256(2) Uani 1 1 d . . .


_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
C1A C2A 1.346(5) . ?
C1A C9A 1.470(5) . ?
C1A S1A 1.778(3) . ?
C2A C15A 1.471(5) . ?
C2A C3A 1.482(5) . ?
C3A C8A 1.390(5) . ?
C3A C4A 1.393(5) . ?
C4A C5A 1.371(5) . ?
C4A S1A 1.767(4) . ?
C5A C6A 1.390(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.381(5) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.389(5) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C9A C14A 1.378(5) . ?
C9A C10A 1.391(5) . ?
C10A C11A 1.387(5) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.361(6) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.381(6) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.385(5) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A C16A 1.392(5) . ?
C15A C20A 1.397(5) . ?
C16A C17A 1.377(5) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.388(5) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.373(5) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.391(5) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C1B C2B 1.330(5) . ?
C1B C9B 1.481(5) . ?
C1B S1B 1.787(4) . ?
C2B C15B 1.487(5) . ?
C2B C3B 1.493(5) . ?
C3B C4B 1.388(5) . ?
C3B C8B 1.391(5) . ?
C4B C5B 1.367(5) . ?
C4B S1B 1.771(4) . ?
C5B C6B 1.386(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.385(5) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.382(5) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.393(5) . ?
C9B C14B 1.394(5) . ?
C10B C11B 1.380(5) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.374(6) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.375(5) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.375(5) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15B C16B 1.378(5) . ?
C15B C20B 1.388(5) . ?
C16B C17B 1.392(5) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.367(6) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.384(6) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.393(5) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
O1A S1A 1.438(3) . ?
O2A S1A 1.442(3) . ?
O1B S1B 1.444(2) . ?
O2B S1B 1.442(3) . ?

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
C2A C1A C9A 133.4(3) . . ?
C2A C1A S1A 109.9(3) . . ?
C9A C1A S1A 116.7(2) . . ?
C1A C2A C15A 124.6(3) . . ?
C1A C2A C3A 113.6(3) . . ?
C15A C2A C3A 121.7(3) . . ?
C8A C3A C4A 116.8(3) . . ?
C8A C3A C2A 128.9(3) . . ?
C4A C3A C2A 114.2(3) . . ?
C5A C4A C3A 124.5(3) . . ?
C5A C4A S1A 127.3(3) . . ?
C3A C4A S1A 108.1(3) . . ?
C4A C5A C6A 117.5(4) . . ?
C4A C5A H5A 121.3 . . ?
C6A C5A H5A 121.3 . . ?
C7A C6A C5A 119.9(4) . . ?
C7A C6A H6A 120.1 . . ?
C5A C6A H6A 120.1 . . ?
C6A C7A C8A 121.4(4) . . ?
C6A C7A H7A 119.3 . . ?
C8A C7A H7A 119.3 . . ?
C7A C8A C3A 119.9(3) . . ?
C7A C8A H8A 120.1 . . ?
C3A C8A H8A 120.1 . . ?
C14A C9A C10A 118.4(4) . . ?
C14A C9A C1A 122.4(3) . . ?
C10A C9A C1A 119.1(3) . . ?
C11A C10A C9A 120.9(4) . . ?
C11A C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C12A C11A C10A 120.1(4) . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C12A C13A 119.8(4) . . ?
C11A C12A H12A 120.1 . . ?
C13A C12A H12A 120.1 . . ?
C12A C13A C14A 120.4(4) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C9A C14A C13A 120.5(4) . . ?
C9A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
C16A C15A C20A 119.0(3) . . ?
C16A C15A C2A 120.9(3) . . ?
C20A C15A C2A 120.1(3) . . ?
C17A C16A C15A 120.7(4) . . ?
C17A C16A H16A 119.6 . . ?
C15A C16A H16A 119.6 . . ?
C16A C17A C18A 120.0(4) . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C19A C18A C17A 119.9(4) . . ?
C19A C18A H18A 120.1 . . ?
C17A C18A H18A 120.1 . . ?
C18A C19A C20A 120.7(4) . . ?
C18A C19A H19A 119.7 . . ?
C20A C19A H19A 119.7 . . ?
C19A C20A C15A 119.7(4) . . ?
C19A C20A H20A 120.2 . . ?
C15A C20A H20A 120.2 . . ?
C2B C1B C9B 132.1(3) . . ?
C2B C1B S1B 110.2(3) . . ?
C9B C1B S1B 117.4(3) . . ?
C1B C2B C15B 125.9(3) . . ?
C1B C2B C3B 114.0(3) . . ?
C15B C2B C3B 120.0(3) . . ?
C4B C3B C8B 118.3(3) . . ?
C4B C3B C2B 113.4(3) . . ?
C8B C3B C2B 128.1(3) . . ?
C5B C4B C3B 123.3(3) . . ?
C5B C4B S1B 127.4(3) . . ?
C3B C4B S1B 108.8(3) . . ?
C4B C5B C6B 117.7(3) . . ?
C4B C5B H5B 121.2 . . ?
C6B C5B H5B 121.2 . . ?
C7B C6B C5B 120.4(3) . . ?
C7B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
C8B C7B C6B 121.1(4) . . ?
C8B C7B H7B 119.5 . . ?
C6B C7B H7B 119.5 . . ?
C7B C8B C3B 119.2(4) . . ?
C7B C8B H8B 120.4 . . ?
C3B C8B H8B 120.4 . . ?
C10B C9B C14B 118.5(3) . . ?
C10B C9B C1B 120.5(3) . . ?
C14B C9B C1B 120.9(3) . . ?
C11B C10B C9B 120.7(4) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
C12B C11B C10B 120.6(4) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C13B C12B C11B 118.8(4) . . ?
C13B C12B H12B 120.6 . . ?
C11B C12B H12B 120.6 . . ?
C12B C13B C14B 121.8(4) . . ?
C12B C13B H13B 119.1 . . ?
C14B C13B H13B 119.1 . . ?
C13B C14B C9B 119.6(4) . . ?
C13B C14B H14B 120.2 . . ?
C9B C14B H14B 120.2 . . ?
C16B C15B C20B 119.7(3) . . ?
C16B C15B C2B 120.2(4) . . ?
C20B C15B C2B 120.1(3) . . ?
C15B C16B C17B 120.4(4) . . ?
C15B C16B H16B 119.8 . . ?
C17B C16B H16B 119.8 . . ?
C18B C17B C16B 119.9(4) . . ?
C18B C17B H17B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C17B C18B C19B 120.3(4) . . ?
C17B C18B H18B 119.8 . . ?
C19B C18B H18B 119.8 . . ?
C18B C19B C20B 119.9(4) . . ?
C18B C19B H19B 120.1 . . ?
C20B C19B H19B 120.1 . . ?
C15B C20B C19B 119.7(4) . . ?
C15B C20B H20B 120.1 . . ?
C19B C20B H20B 120.1 . . ?
O1A S1A O2A 117.08(17) . . ?
O1A S1A C4A 111.24(17) . . ?
O2A S1A C4A 110.76(17) . . ?
O1A S1A C1A 112.31(16) . . ?
O2A S1A C1A 109.09(17) . . ?
C4A S1A C1A 93.99(17) . . ?
O2B S1B O1B 116.96(15) . . ?
O2B S1B C4B 113.10(17) . . ?
O1B S1B C4B 109.65(16) . . ?
O2B S1B C1B 109.78(17) . . ?
O1B S1B C1B 111.57(16) . . ?
C4B S1B C1B 93.35(17) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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 1501900'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 O2 S'
_chemical_formula_sum            'C22 H18 O2 S'
_chemical_formula_weight         346.42

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1340(5)
_cell_length_b                   10.9037(6)
_cell_length_c                   17.7060(9)
_cell_angle_alpha                90.049(2)
_cell_angle_beta                 92.799(2)
_cell_angle_gamma                114.437(2)
_cell_volume                     1778.61(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4726
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17607
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.41
_reflns_number_total             6446
_reflns_number_gt                4207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.5381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6446
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C -0.0176(3) 0.1903(3) 0.44235(16) 0.0246(7) Uani 1 1 d . . .
C2A C -0.0516(3) 0.1212(3) 0.37588(16) 0.0228(6) Uani 1 1 d . . .
C3A C -0.2099(3) 0.0601(3) 0.35425(16) 0.0244(7) Uani 1 1 d . . .
C4A C -0.2922(3) 0.0883(3) 0.40641(17) 0.0257(7) Uani 1 1 d . . .
C5A C -0.4408(3) 0.0462(3) 0.39682(18) 0.0322(8) Uani 1 1 d . . .
H5A H -0.4942 0.0678 0.4332 0.039 Uiso 1 1 calc R . .
C6A C -0.5087(3) -0.0288(3) 0.33179(18) 0.0370(8) Uani 1 1 d . . .
H6A H -0.6109 -0.0606 0.3235 0.044 Uiso 1 1 calc R . .
C7A C -0.4295(3) -0.0576(3) 0.27923(19) 0.0380(8) Uani 1 1 d . . .
H7A H -0.4783 -0.1096 0.2352 0.046 Uiso 1 1 calc R . .
C8A C -0.2792(3) -0.0123(3) 0.28896(17) 0.0322(7) Uani 1 1 d . . .
H8A H -0.2255 -0.0307 0.2515 0.039 Uiso 1 1 calc R . .
C9A C 0.1229(3) 0.2566(3) 0.48587(16) 0.0238(7) Uani 1 1 d . . .
C10A C 0.2120(3) 0.1884(3) 0.49625(18) 0.0342(8) Uani 1 1 d . . .
H10A H 0.1824 0.1005 0.4749 0.041 Uiso 1 1 calc R . .
C11A C 0.3430(3) 0.2480(3) 0.53739(18) 0.0374(8) Uani 1 1 d . . .
H11A H 0.4026 0.2002 0.5437 0.045 Uiso 1 1 calc R . .
C12A C 0.3896(3) 0.3760(3) 0.56968(16) 0.0312(7) Uani 1 1 d . . .
C13A C 0.3005(3) 0.4429(3) 0.55879(17) 0.0321(7) Uani 1 1 d . . .
H13A H 0.3305 0.5310 0.5800 0.039 Uiso 1 1 calc R . .
C14A C 0.1687(3) 0.3846(3) 0.51781(16) 0.0281(7) Uani 1 1 d . . .
H14A H 0.1093 0.4326 0.5115 0.034 Uiso 1 1 calc R . .
C15A C 0.5323(3) 0.4390(4) 0.61549(19) 0.0461(9) Uani 1 1 d . . .
H15A H 0.5655 0.5372 0.6172 0.069 Uiso 1 1 calc R . .
H15B H 0.6048 0.4159 0.5919 0.069 Uiso 1 1 calc R . .
H15C H 0.5193 0.4049 0.6670 0.069 Uiso 1 1 calc R . .
C16A C 0.0549(3) 0.1117(3) 0.32475(16) 0.0258(7) Uani 1 1 d . . .
C17A C 0.0460(3) -0.0117(3) 0.29809(17) 0.0326(7) Uani 1 1 d . . .
H17A H -0.0275 -0.0931 0.3146 0.039 Uiso 1 1 calc R . .
C18A C 0.1441(4) -0.0160(4) 0.24761(18) 0.0385(8) Uani 1 1 d . . .
H18A H 0.1365 -0.1012 0.2301 0.046 Uiso 1 1 calc R . .
C19A C 0.2527(3) 0.0993(4) 0.22186(18) 0.0376(8) Uani 1 1 d . . .
C20A C 0.2620(3) 0.2225(3) 0.24936(18) 0.0378(8) Uani 1 1 d . . .
H20A H 0.3359 0.3036 0.2329 0.045 Uiso 1 1 calc R . .
C21A C 0.1657(3) 0.2289(3) 0.30021(17) 0.0291(7) Uani 1 1 d . . .
H21A H 0.1751 0.3142 0.3187 0.035 Uiso 1 1 calc R . .
C22A C 0.3551(4) 0.0932(4) 0.1645(2) 0.0631(12) Uani 1 1 d . . .
H22A H 0.3279 -0.0009 0.1490 0.095 Uiso 1 1 calc R . .
H22B H 0.4545 0.1313 0.1870 0.095 Uiso 1 1 calc R . .
H22C H 0.3495 0.1450 0.1202 0.095 Uiso 1 1 calc R . .
C1B C 0.1436(3) 0.4510(3) 0.08525(16) 0.0212(6) Uani 1 1 d . . .
C2B C 0.0294(3) 0.3696(3) 0.12417(16) 0.0226(6) Uani 1 1 d . . .
C3B C 0.0205(3) 0.4243(3) 0.19910(16) 0.0244(7) Uani 1 1 d . . .
C4B C 0.1372(3) 0.5458(3) 0.21829(16) 0.0261(7) Uani 1 1 d . . .
C5B C 0.1536(3) 0.6122(3) 0.28658(18) 0.0351(8) Uani 1 1 d . . .
H5B H 0.2360 0.6938 0.2986 0.042 Uiso 1 1 calc R . .
C6B C 0.0459(4) 0.5560(3) 0.33697(18) 0.0403(8) Uani 1 1 d . . .
H6B H 0.0532 0.5997 0.3844 0.048 Uiso 1 1 calc R . .
C7B C -0.0729(4) 0.4361(3) 0.31879(18) 0.0369(8) Uani 1 1 d . . .
H7B H -0.1465 0.3994 0.3539 0.044 Uiso 1 1 calc R . .
C8B C -0.0865(3) 0.3688(3) 0.25043(17) 0.0301(7) Uani 1 1 d . . .
H8B H -0.1678 0.2860 0.2390 0.036 Uiso 1 1 calc R . .
C9B C 0.1833(3) 0.4410(3) 0.00734(16) 0.0231(7) Uani 1 1 d . . .
C10B C 0.0776(3) 0.3659(3) -0.04758(16) 0.0280(7) Uani 1 1 d . . .
H10B H -0.0204 0.3199 -0.0345 0.034 Uiso 1 1 calc R . .
C11B C 0.1139(3) 0.3577(3) -0.12094(17) 0.0318(8) Uani 1 1 d . . .
H11B H 0.0401 0.3045 -0.1573 0.038 Uiso 1 1 calc R . .
C12B C 0.2553(3) 0.4250(3) -0.14325(17) 0.0312(7) Uani 1 1 d . . .
C13B C 0.3594(3) 0.5026(3) -0.08853(17) 0.0311(7) Uani 1 1 d . . .
H13B H 0.4566 0.5515 -0.1022 0.037 Uiso 1 1 calc R . .
C14B C 0.3251(3) 0.5104(3) -0.01466(17) 0.0275(7) Uani 1 1 d . . .
H14B H 0.3989 0.5637 0.0216 0.033 Uiso 1 1 calc R . .
C15B C 0.2941(4) 0.4127(4) -0.22296(18) 0.0475(9) Uani 1 1 d . . .
H15D H 0.3554 0.5022 -0.2411 0.071 Uiso 1 1 calc R . .
H15E H 0.2052 0.3727 -0.2557 0.071 Uiso 1 1 calc R . .
H15F H 0.3469 0.3551 -0.2241 0.071 Uiso 1 1 calc R . .
C16B C -0.0756(3) 0.2323(3) 0.10026(16) 0.0227(6) Uani 1 1 d . . .
C17B C -0.2236(3) 0.1987(3) 0.09018(17) 0.0274(7) Uani 1 1 d . . .
H17B H -0.2593 0.2659 0.0961 0.033 Uiso 1 1 calc R . .
C18B C -0.3189(3) 0.0676(3) 0.07160(17) 0.0293(7) Uani 1 1 d . . .
H18B H -0.4196 0.0462 0.0641 0.035 Uiso 1 1 calc R . .
C19B C -0.2706(3) -0.0339(3) 0.06361(16) 0.0259(7) Uani 1 1 d . . .
C20B C -0.1228(3) 0.0012(3) 0.07371(17) 0.0315(7) Uani 1 1 d . . .
H20B H -0.0869 -0.0660 0.0681 0.038 Uiso 1 1 calc R . .
C21B C -0.0274(3) 0.1312(3) 0.09164(17) 0.0289(7) Uani 1 1 d . . .
H21B H 0.0734 0.1525 0.0983 0.035 Uiso 1 1 calc R . .
C22B C -0.3761(3) -0.1774(3) 0.04606(19) 0.0410(9) Uani 1 1 d . . .
H22D H -0.3310 -0.2209 0.0139 0.061 Uiso 1 1 calc R . .
H22E H -0.4637 -0.1783 0.0195 0.061 Uiso 1 1 calc R . .
H22F H -0.4022 -0.2264 0.0933 0.061 Uiso 1 1 calc R . .
O1A O -0.2042(2) 0.11229(19) 0.55160(11) 0.0322(5) Uani 1 1 d . . .
O2A O -0.1803(2) 0.31622(18) 0.48571(11) 0.0303(5) Uani 1 1 d . . .
O1B O 0.2655(2) 0.71869(19) 0.11277(12) 0.0350(5) Uani 1 1 d . . .
O2B O 0.3901(2) 0.5851(2) 0.16690(12) 0.0359(5) Uani 1 1 d . . .
S1A S -0.17790(8) 0.18528(7) 0.48251(4) 0.02496(19) Uani 1 1 d . . .
S1B S 0.25552(7) 0.59365(7) 0.14425(4) 0.0265(2) Uani 1 1 d . . .


_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
C1A C2A 1.348(4) . ?
C1A C9A 1.478(4) . ?
C1A S1A 1.785(3) . ?
C2A C16A 1.477(4) . ?
C2A C3A 1.490(4) . ?
C3A C8A 1.383(4) . ?
C3A C4A 1.389(4) . ?
C4A C5A 1.383(4) . ?
C4A S1A 1.763(3) . ?
C5A C6A 1.387(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.375(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.395(4) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C9A C14A 1.386(4) . ?
C9A C10A 1.393(4) . ?
C10A C11A 1.381(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.388(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.382(4) . ?
C12A C15A 1.512(4) . ?
C13A C14A 1.385(4) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A C17A 1.390(4) . ?
C16A C21A 1.395(4) . ?
C17A C18A 1.384(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.380(5) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.393(4) . ?
C19A C22A 1.508(4) . ?
C20A C21A 1.382(4) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C1B C2B 1.353(4) . ?
C1B C9B 1.472(4) . ?
C1B S1B 1.794(3) . ?
C2B C3B 1.476(4) . ?
C2B C16B 1.480(4) . ?
C3B C8B 1.387(4) . ?
C3B C4B 1.390(4) . ?
C4B C5B 1.376(4) . ?
C4B S1B 1.751(3) . ?
C5B C6B 1.380(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.385(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.386(4) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.391(4) . ?
C9B C14B 1.394(4) . ?
C10B C11B 1.380(4) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.391(4) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.388(4) . ?
C12B C15B 1.504(4) . ?
C13B C14B 1.381(4) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B C17B 1.391(4) . ?
C16B C21B 1.389(4) . ?
C17B C18B 1.382(4) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.392(4) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.386(4) . ?
C19B C22B 1.507(4) . ?
C20B C21B 1.371(4) . ?
C20B H20B 0.9500 . ?
C21B H21B 0.9500 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
O1A S1A 1.435(2) . ?
O2A S1A 1.4390(19) . ?
O1B S1B 1.440(2) . ?
O2B S1B 1.4423(19) . ?

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
C2A C1A C9A 130.7(3) . . ?
C2A C1A S1A 110.2(2) . . ?
C9A C1A S1A 118.9(2) . . ?
C1A C2A C16A 125.0(2) . . ?
C1A C2A C3A 113.8(3) . . ?
C16A C2A C3A 121.1(2) . . ?
C8A C3A C4A 118.7(3) . . ?
C8A C3A C2A 128.1(3) . . ?
C4A C3A C2A 113.1(2) . . ?
C5A C4A C3A 123.3(3) . . ?
C5A C4A S1A 127.1(2) . . ?
C3A C4A S1A 109.6(2) . . ?
C4A C5A C6A 117.2(3) . . ?
C4A C5A H5A 121.4 . . ?
C6A C5A H5A 121.4 . . ?
C7A C6A C5A 120.6(3) . . ?
C7A C6A H6A 119.7 . . ?
C5A C6A H6A 119.7 . . ?
C6A C7A C8A 121.6(3) . . ?
C6A C7A H7A 119.2 . . ?
C8A C7A H7A 119.2 . . ?
C3A C8A C7A 118.7(3) . . ?
C3A C8A H8A 120.7 . . ?
C7A C8A H8A 120.7 . . ?
C14A C9A C10A 118.5(3) . . ?
C14A C9A C1A 122.0(2) . . ?
C10A C9A C1A 119.4(3) . . ?
C11A C10A C9A 120.3(3) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
C10A C11A C12A 121.5(3) . . ?
C10A C11A H11A 119.3 . . ?
C12A C11A H11A 119.3 . . ?
C13A C12A C11A 117.6(3) . . ?
C13A C12A C15A 121.5(3) . . ?
C11A C12A C15A 120.9(3) . . ?
C14A C13A C12A 121.6(3) . . ?
C14A C13A H13A 119.2 . . ?
C12A C13A H13A 119.2 . . ?
C13A C14A C9A 120.3(3) . . ?
C13A C14A H14A 119.8 . . ?
C9A C14A H14A 119.8 . . ?
C12A C15A H15A 109.5 . . ?
C12A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C12A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C17A C16A C21A 118.3(3) . . ?
C17A C16A C2A 121.9(3) . . ?
C21A C16A C2A 119.8(3) . . ?
C18A C17A C16A 120.1(3) . . ?
C18A C17A H17A 119.9 . . ?
C16A C17A H17A 119.9 . . ?
C19A C18A C17A 122.2(3) . . ?
C19A C18A H18A 118.9 . . ?
C17A C18A H18A 118.9 . . ?
C18A C19A C20A 117.5(3) . . ?
C18A C19A C22A 121.6(3) . . ?
C20A C19A C22A 120.9(3) . . ?
C21A C20A C19A 121.2(3) . . ?
C21A C20A H20A 119.4 . . ?
C19A C20A H20A 119.4 . . ?
C20A C21A C16A 120.7(3) . . ?
C20A C21A H21A 119.6 . . ?
C16A C21A H21A 119.6 . . ?
C19A C22A H22A 109.5 . . ?
C19A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C19A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C2B C1B C9B 131.4(2) . . ?
C2B C1B S1B 109.0(2) . . ?
C9B C1B S1B 119.6(2) . . ?
C1B C2B C3B 114.3(2) . . ?
C1B C2B C16B 125.9(3) . . ?
C3B C2B C16B 119.7(2) . . ?
C8B C3B C4B 118.5(3) . . ?
C8B C3B C2B 128.1(3) . . ?
C4B C3B C2B 113.4(3) . . ?
C5B C4B C3B 123.2(3) . . ?
C5B C4B S1B 127.4(2) . . ?
C3B C4B S1B 109.4(2) . . ?
C4B C5B C6B 117.6(3) . . ?
C4B C5B H5B 121.2 . . ?
C6B C5B H5B 121.2 . . ?
C5B C6B C7B 120.4(3) . . ?
C5B C6B H6B 119.8 . . ?
C7B C6B H6B 119.8 . . ?
C6B C7B C8B 121.4(3) . . ?
C6B C7B H7B 119.3 . . ?
C8B C7B H7B 119.3 . . ?
C7B C8B C3B 118.8(3) . . ?
C7B C8B H8B 120.6 . . ?
C3B C8B H8B 120.6 . . ?
C10B C9B C14B 118.0(3) . . ?
C10B C9B C1B 120.3(2) . . ?
C14B C9B C1B 121.6(2) . . ?
C11B C10B C9B 120.5(3) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
C10B C11B C12B 121.9(3) . . ?
C10B C11B H11B 119.0 . . ?
C12B C11B H11B 119.0 . . ?
C13B C12B C11B 117.1(3) . . ?
C13B C12B C15B 121.5(3) . . ?
C11B C12B C15B 121.4(3) . . ?
C14B C13B C12B 121.6(3) . . ?
C14B C13B H13B 119.2 . . ?
C12B C13B H13B 119.2 . . ?
C13B C14B C9B 120.8(3) . . ?
C13B C14B H14B 119.6 . . ?
C9B C14B H14B 119.6 . . ?
C12B C15B H15D 109.5 . . ?
C12B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C12B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C17B C16B C21B 118.4(3) . . ?
C17B C16B C2B 122.0(2) . . ?
C21B C16B C2B 119.6(2) . . ?
C18B C17B C16B 120.2(3) . . ?
C18B C17B H17B 119.9 . . ?
C16B C17B H17B 119.9 . . ?
C17B C18B C19B 121.4(3) . . ?
C17B C18B H18B 119.3 . . ?
C19B C18B H18B 119.3 . . ?
C20B C19B C18B 117.8(3) . . ?
C20B C19B C22B 121.3(3) . . ?
C18B C19B C22B 120.9(3) . . ?
C21B C20B C19B 121.1(3) . . ?
C21B C20B H20B 119.4 . . ?
C19B C20B H20B 119.4 . . ?
C20B C21B C16B 121.1(3) . . ?
C20B C21B H21B 119.4 . . ?
C16B C21B H21B 119.4 . . ?
C19B C22B H22D 109.5 . . ?
C19B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C19B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O1A S1A O2A 116.15(12) . . ?
O1A S1A C4A 111.91(13) . . ?
O2A S1A C4A 110.34(12) . . ?
O1A S1A C1A 110.88(13) . . ?
O2A S1A C1A 112.06(12) . . ?
C4A S1A C1A 93.24(13) . . ?
O1B S1B O2B 117.03(12) . . ?
O1B S1B C4B 111.07(13) . . ?
O2B S1B C4B 110.28(13) . . ?
O1B S1B C1B 112.14(12) . . ?
O2B S1B C1B 110.22(12) . . ?
C4B S1B C1B 93.69(13) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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 1501897'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H12 F6 O2 S'
_chemical_formula_sum            'C22 H12 F6 O2 S'
_chemical_formula_weight         454.38

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5333(4)
_cell_length_b                   10.9876(7)
_cell_length_c                   11.6354(8)
_cell_angle_alpha                91.853(3)
_cell_angle_beta                 90.826(2)
_cell_angle_gamma                95.099(2)
_cell_volume                     958.64(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    174(2)
_cell_measurement_reflns_used    2550
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      25.19

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      174(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8525
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3458
_reflns_number_gt                2385
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0261P)²+0.6601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3458
_refine_ls_number_parameters     355
_refine_ls_number_restraints     388
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4810(3) 0.6061(2) 0.6875(2) 0.0203(6) Uani 1 1 d . . .
C2 C 0.5455(3) 0.7101(2) 0.6392(2) 0.0203(6) Uani 1 1 d . . .
C3 C 0.4387(3) 0.7455(2) 0.5395(2) 0.0203(6) Uani 1 1 d . . .
C4 C 0.2898(3) 0.6640(2) 0.5148(2) 0.0225(6) Uani 1 1 d . . .
C5 C 0.1728(4) 0.6776(3) 0.4248(2) 0.0290(7) Uani 1 1 d . . .
H5 H 0.0722 0.6204 0.4103 0.035 Uiso 1 1 calc R . .
C6 C 0.2072(4) 0.7773(3) 0.3564(2) 0.0317(7) Uani 1 1 d . . .
H6 H 0.1293 0.7893 0.2937 0.038 Uiso 1 1 calc R . .
C7 C 0.3542(4) 0.8596(3) 0.3788(2) 0.0304(7) Uani 1 1 d . . .
H7 H 0.3762 0.9276 0.3310 0.036 Uiso 1 1 calc R . .
C8 C 0.4706(3) 0.8445(3) 0.4701(2) 0.0259(7) Uani 1 1 d . . .
H8 H 0.5711 0.9017 0.4846 0.031 Uiso 1 1 calc R . .
C9 C 0.5548(3) 0.5286(2) 0.7734(2) 0.0233(6) Uani 1 1 d . A .
C10 C 0.7376(4) 0.5312(3) 0.7933(2) 0.0277(7) Uani 1 1 d . . .
H10 H 0.8156 0.5891 0.7555 0.033 Uiso 1 1 calc R . .
C11 C 0.8074(4) 0.4512(3) 0.8668(2) 0.0329(7) Uani 1 1 d . A .
H11 H 0.9326 0.4551 0.8796 0.039 Uiso 1 1 calc R . .
C12 C 0.6966(4) 0.3655(3) 0.9219(2) 0.0339(7) Uani 1 1 d D . .
C13 C 0.5141(4) 0.3622(3) 0.9045(3) 0.0406(8) Uani 1 1 d . A .
H13 H 0.4370 0.3043 0.9429 0.049 Uiso 1 1 calc R . .
C14 C 0.4442(4) 0.4425(3) 0.8318(3) 0.0354(8) Uani 1 1 d . . .
H14 H 0.3187 0.4396 0.8209 0.043 Uiso 1 1 calc R A .
C16 C 0.7091(3) 0.7879(2) 0.6760(2) 0.0197(6) Uani 1 1 d . . .
C17 C 0.8477(3) 0.8110(2) 0.5988(2) 0.0249(7) Uani 1 1 d . . .
H17 H 0.8378 0.7762 0.5229 0.030 Uiso 1 1 calc R . .
C18 C 0.9988(3) 0.8844(2) 0.6327(2) 0.0251(7) Uani 1 1 d . . .
H18 H 1.0930 0.8995 0.5802 0.030 Uiso 1 1 calc R . .
C19 C 1.0138(3) 0.9362(2) 0.7431(2) 0.0224(6) Uani 1 1 d . . .
C20 C 0.8764(3) 0.9149(3) 0.8199(2) 0.0254(7) Uani 1 1 d . . .
H20 H 0.8860 0.9509 0.8953 0.030 Uiso 1 1 calc R . .
C21 C 0.7251(3) 0.8409(2) 0.7862(2) 0.0245(6) Uani 1 1 d . . .
H21 H 0.6311 0.8262 0.8389 0.029 Uiso 1 1 calc R . .
C22 C 1.1778(4) 1.0166(3) 0.7758(2) 0.0298(7) Uani 1 1 d . . .
F4 F 1.3265(2) 0.96277(17) 0.75368(17) 0.0544(6) Uani 1 1 d . . .
F5 F 1.1941(2) 1.11904(17) 0.71722(17) 0.0558(6) Uani 1 1 d . . .
F6 F 1.1878(2) 1.0496(2) 0.88620(15) 0.0636(7) Uani 1 1 d . . .
O1 O 0.2972(2) 0.43103(17) 0.56097(16) 0.0329(5) Uani 1 1 d . . .
O2 O 0.1279(2) 0.55764(18) 0.68803(16) 0.0334(5) Uani 1 1 d . . .
S1 S 0.27845(9) 0.54825(6) 0.61496(6) 0.02448(19) Uani 1 1 d . . .
C15 C 0.7693(17) 0.2713(12) 0.9937(11) 0.047(2) Uani 0.318(4) 1 d PDU A 1
F1 F 0.720(2) 0.2787(12) 1.1035(7) 0.046(3) Uani 0.318(4) 1 d PDU A 1
F2 F 0.9474(11) 0.2766(14) 0.9925(14) 0.062(3) Uani 0.318(4) 1 d PDU A 1
F3 F 0.711(2) 0.1570(7) 0.9566(9) 0.057(3) Uani 0.318(4) 1 d PDU A 1
C15' C 0.7641(18) 0.2686(11) 0.9930(11) 0.048(2) Uani 0.279(6) 1 d PDU A 2
F1' F 0.9075(14) 0.2226(10) 0.9471(9) 0.044(2) Uani 0.279(6) 1 d PDU A 2
F2' F 0.6446(12) 0.1715(9) 1.0074(13) 0.064(3) Uani 0.279(6) 1 d PDU A 2
F3' F 0.815(2) 0.3134(10) 1.0978(7) 0.060(3) Uani 0.279(6) 1 d PDU A 2
C15A C 0.7804(15) 0.2799(10) 0.9987(9) 0.045(2) Uani 0.403(7) 1 d PDU A 3
F1A F 0.9384(10) 0.3229(7) 1.0470(8) 0.057(2) Uani 0.403(7) 1 d PDU A 3
F2A F 0.6749(12) 0.2454(10) 1.0859(8) 0.057(3) Uani 0.403(7) 1 d PDU A 3
F3A F 0.8101(16) 0.1756(7) 0.9417(6) 0.057(2) Uani 0.403(7) 1 d PDU A 3


_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
C1 C2 1.345(4) . ?
C1 C9 1.469(4) . ?
C1 S1 1.789(2) . ?
C2 C3 1.484(4) . ?
C2 C16 1.485(3) . ?
C3 C8 1.382(4) . ?
C3 C4 1.392(3) . ?
C4 C5 1.379(4) . ?
C4 S1 1.750(3) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 C14 1.403(4) . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C12 C15 1.487(11) . ?
C12 C15' 1.489(12) . ?
C12 C15A 1.491(10) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C21 1.390(3) . ?
C16 C17 1.399(4) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 C22 1.491(4) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 F6 1.322(3) . ?
C22 F5 1.332(3) . ?
C22 F4 1.337(3) . ?
O1 S1 1.4338(19) . ?
O2 S1 1.4365(18) . ?
C15 F2 1.338(12) . ?
C15 F1 1.338(12) . ?
C15 F3 1.348(12) . ?
C15' F3' 1.337(12) . ?
C15' F1' 1.343(12) . ?
C15' F2' 1.350(12) . ?
C15A F2A 1.341(11) . ?
C15A F3A 1.343(10) . ?
C15A F1A 1.349(10) . ?

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
C2 C1 C9 132.7(2) . . ?
C2 C1 S1 109.4(2) . . ?
C9 C1 S1 117.39(19) . . ?
C1 C2 C3 114.3(2) . . ?
C1 C2 C16 126.2(2) . . ?
C3 C2 C16 119.5(2) . . ?
C8 C3 C4 118.2(2) . . ?
C8 C3 C2 128.7(2) . . ?
C4 C3 C2 113.1(2) . . ?
C5 C4 C3 123.2(3) . . ?
C5 C4 S1 127.5(2) . . ?
C3 C4 S1 109.3(2) . . ?
C4 C5 C6 117.7(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 119.4(2) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C14 117.6(3) . . ?
C10 C9 C1 121.2(2) . . ?
C14 C9 C1 121.0(2) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 C15 121.5(6) . . ?
C13 C12 C15 119.0(6) . . ?
C11 C12 C15' 123.1(6) . . ?
C13 C12 C15' 117.3(6) . . ?
C15 C12 C15' 1.8(9) . . ?
C11 C12 C15A 118.0(5) . . ?
C13 C12 C15A 122.6(5) . . ?
C15 C12 C15A 5.1(8) . . ?
C15' C12 C15A 6.8(8) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C21 C16 C17 119.1(2) . . ?
C21 C16 C2 120.8(2) . . ?
C17 C16 C2 120.1(2) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 C22 121.3(2) . . ?
C18 C19 C22 118.7(2) . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C16 120.7(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
F6 C22 F5 106.9(2) . . ?
F6 C22 F4 105.9(2) . . ?
F5 C22 F4 104.7(2) . . ?
F6 C22 C19 113.6(2) . . ?
F5 C22 C19 112.8(2) . . ?
F4 C22 C19 112.2(2) . . ?
O1 S1 O2 116.93(12) . . ?
O1 S1 C4 111.50(12) . . ?
O2 S1 C4 110.49(12) . . ?
O1 S1 C1 110.70(12) . . ?
O2 S1 C1 111.05(11) . . ?
C4 S1 C1 93.81(12) . . ?
F2 C15 F1 107.8(10) . . ?
F2 C15 F3 106.0(10) . . ?
F1 C15 F3 105.0(10) . . ?
F2 C15 C12 112.7(9) . . ?
F1 C15 C12 112.9(10) . . ?
F3 C15 C12 111.9(9) . . ?
F3' C15' F1' 106.4(10) . . ?
F3' C15' F2' 107.2(10) . . ?
F1' C15' F2' 105.5(10) . . ?
F3' C15' C12 110.8(9) . . ?
F1' C15' C12 112.3(9) . . ?
F2' C15' C12 114.1(9) . . ?
F2A C15A F3A 105.2(9) . . ?
F2A C15A F1A 106.1(9) . . ?
F3A C15A F1A 105.9(8) . . ?
F2A C15A C12 112.3(8) . . ?
F3A C15A C12 111.2(8) . . ?
F1A C15A C12 115.5(8) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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 1501894'
_audit_update_record             
;
2016-08-31 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 O2 S'
_chemical_formula_sum            'C28 H30 O2 S'
_chemical_formula_weight         430.58

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   16.9872(11)
_cell_length_b                   11.0288(9)
_cell_length_c                   12.9726(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.237(2)
_cell_angle_gamma                90.00
_cell_volume                     2383.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6566
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13303
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_sigmaI/netI    0.0948
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.36
_reflns_number_total             4318
_reflns_number_gt                2688
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0384P)²+1.6015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21940(17) 0.9777(3) 0.5875(2) 0.0179(7) Uani 1 1 d . . .
C2 C 0.17249(17) 1.0220(3) 0.4997(2) 0.0197(7) Uani 1 1 d . . .
C3 C 0.10038(17) 1.0883(3) 0.5195(2) 0.0206(7) Uani 1 1 d . . .
C4 C 0.09633(17) 1.0948(3) 0.6254(2) 0.0212(7) Uani 1 1 d . . .
C5 C 0.03684(18) 1.1565(3) 0.6629(3) 0.0275(8) Uani 1 1 d . . .
H5 H 0.0357 1.1587 0.7358 0.033 Uiso 1 1 calc R . .
C6 C -0.02112(19) 1.2153(3) 0.5895(3) 0.0298(9) Uani 1 1 d . . .
H6 H -0.0615 1.2619 0.6123 0.036 Uiso 1 1 calc R . .
C7 C -0.02018(18) 1.2061(3) 0.4839(3) 0.0296(9) Uani 1 1 d . . .
H7 H -0.0614 1.2442 0.4346 0.036 Uiso 1 1 calc R . .
C8 C 0.03948(18) 1.1425(3) 0.4476(3) 0.0239(8) Uani 1 1 d . . .
H8 H 0.0386 1.1363 0.3744 0.029 Uiso 1 1 calc R . .
C9 C 0.29857(18) 0.9172(3) 0.6085(2) 0.0200(7) Uani 1 1 d . . .
C10 C 0.34882(18) 0.9170(3) 0.5353(3) 0.0259(8) Uani 1 1 d . . .
H10 H 0.3326 0.9579 0.4702 0.031 Uiso 1 1 calc R . .
C11 C 0.42203(19) 0.8578(3) 0.5566(3) 0.0301(9) Uani 1 1 d . . .
H11 H 0.4549 0.8589 0.5051 0.036 Uiso 1 1 calc R . .
C12 C 0.44927(18) 0.7966(3) 0.6510(3) 0.0253(8) Uani 1 1 d . . .
C13 C 0.40011(19) 0.8010(3) 0.7242(3) 0.0282(8) Uani 1 1 d . . .
H13 H 0.4173 0.7625 0.7903 0.034 Uiso 1 1 calc R . .
C14 C 0.32697(18) 0.8594(3) 0.7044(3) 0.0250(8) Uani 1 1 d . . .
H14 H 0.2952 0.8605 0.7571 0.030 Uiso 1 1 calc R . .
C15 C 0.5284(2) 0.7270(3) 0.6687(3) 0.0337(9) Uani 1 1 d . . .
C16 C 0.5195(2) 0.6186(4) 0.5940(4) 0.0600(13) Uani 1 1 d . . .
H16A H 0.4779 0.5640 0.6099 0.090 Uiso 1 1 calc R . .
H16B H 0.5707 0.5751 0.6028 0.090 Uiso 1 1 calc R . .
H16C H 0.5042 0.6472 0.5213 0.090 Uiso 1 1 calc R . .
C17 C 0.5537(2) 0.6813(4) 0.7812(3) 0.0590(13) Uani 1 1 d . . .
H17A H 0.5568 0.7497 0.8300 0.088 Uiso 1 1 calc R . .
H17B H 0.6063 0.6421 0.7897 0.088 Uiso 1 1 calc R . .
H17C H 0.5141 0.6226 0.7963 0.088 Uiso 1 1 calc R . .
C18 C 0.5958(2) 0.8085(4) 0.6446(4) 0.0575(13) Uani 1 1 d . . .
H18A H 0.5833 0.8330 0.5706 0.086 Uiso 1 1 calc R . .
H18B H 0.6466 0.7637 0.6584 0.086 Uiso 1 1 calc R . .
H18C H 0.6006 0.8807 0.6894 0.086 Uiso 1 1 calc R . .
C19 C 0.18610(16) 1.0152(3) 0.3904(2) 0.0188(7) Uani 1 1 d . . .
C20 C 0.18996(18) 1.1215(3) 0.3339(2) 0.0222(8) Uani 1 1 d . . .
H20 H 0.1849 1.1975 0.3664 0.027 Uiso 1 1 calc R . .
C21 C 0.20103(18) 1.1180(3) 0.2311(2) 0.0238(8) Uani 1 1 d . . .
H21 H 0.2046 1.1921 0.1949 0.029 Uiso 1 1 calc R . .
C22 C 0.20708(16) 1.0088(3) 0.1791(2) 0.0177(7) Uani 1 1 d . . .
C23 C 0.20274(18) 0.9035(3) 0.2365(2) 0.0234(8) Uani 1 1 d . . .
H23 H 0.2067 0.8273 0.2037 0.028 Uiso 1 1 calc R . .
C24 C 0.19286(17) 0.9058(3) 0.3403(2) 0.0201(7) Uani 1 1 d . . .
H24 H 0.1907 0.8319 0.3772 0.024 Uiso 1 1 calc R . .
C25 C 0.21421(18) 1.0106(3) 0.0636(2) 0.0240(7) Uani 1 1 d . . .
C26 C 0.2365(2) 0.8860(3) 0.0255(3) 0.0326(9) Uani 1 1 d . . .
H26A H 0.2885 0.8607 0.0666 0.049 Uiso 1 1 calc R . .
H26B H 0.2398 0.8910 -0.0490 0.049 Uiso 1 1 calc R . .
H26C H 0.1954 0.8268 0.0344 0.049 Uiso 1 1 calc R . .
C27 C 0.1326(2) 1.0485(4) -0.0013(3) 0.0377(10) Uani 1 1 d . . .
H27A H 0.0917 0.9894 0.0090 0.056 Uiso 1 1 calc R . .
H27B H 0.1358 1.0515 -0.0758 0.056 Uiso 1 1 calc R . .
H27C H 0.1181 1.1287 0.0216 0.056 Uiso 1 1 calc R . .
C28 C 0.2786(2) 1.1007(4) 0.0455(3) 0.0413(10) Uani 1 1 d . . .
H28A H 0.2636 1.1825 0.0639 0.062 Uiso 1 1 calc R . .
H28B H 0.2833 1.0987 -0.0286 0.062 Uiso 1 1 calc R . .
H28C H 0.3302 1.0785 0.0897 0.062 Uiso 1 1 calc R . .
O1 O 0.22820(13) 1.0868(2) 0.77234(16) 0.0282(6) Uani 1 1 d . . .
O2 O 0.14492(13) 0.9026(2) 0.74049(17) 0.0286(6) Uani 1 1 d . . .
S1 S 0.17546(5) 1.01074(7) 0.69918(6) 0.0211(2) Uani 1 1 d . . .


_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
C1 C2 1.348(4) . ?
C1 C9 1.478(4) . ?
C1 S1 1.792(3) . ?
C2 C19 1.482(4) . ?
C2 C3 1.491(4) . ?
C3 C8 1.386(4) . ?
C3 C4 1.392(4) . ?
C4 C5 1.383(4) . ?
C4 S1 1.755(3) . ?
C5 C6 1.389(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.394(4) . ?
C9 C14 1.398(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 C15 1.526(4) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C17 1.525(5) . ?
C15 C16 1.528(5) . ?
C15 C18 1.535(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.386(4) . ?
C19 C20 1.390(4) . ?
C20 C21 1.384(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(4) . ?
C22 C25 1.526(4) . ?
C23 C24 1.389(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C28 1.529(5) . ?
C25 C27 1.533(4) . ?
C25 C26 1.533(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O1 S1 1.441(2) . ?
O2 S1 1.445(2) . ?

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
C2 C1 C9 133.3(3) . . ?
C2 C1 S1 109.8(2) . . ?
C9 C1 S1 116.8(2) . . ?
C1 C2 C19 127.8(3) . . ?
C1 C2 C3 113.7(3) . . ?
C19 C2 C3 118.4(3) . . ?
C8 C3 C4 117.9(3) . . ?
C8 C3 C2 128.8(3) . . ?
C4 C3 C2 113.3(3) . . ?
C5 C4 C3 123.6(3) . . ?
C5 C4 S1 127.1(3) . . ?
C3 C4 S1 109.3(2) . . ?
C4 C5 C6 117.2(3) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 119.3(3) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C14 117.0(3) . . ?
C10 C9 C1 122.1(3) . . ?
C14 C9 C1 120.9(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 122.3(3) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 116.4(3) . . ?
C13 C12 C15 123.1(3) . . ?
C11 C12 C15 120.4(3) . . ?
C14 C13 C12 122.1(3) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C17 C15 C16 108.9(3) . . ?
C17 C15 C12 112.7(3) . . ?
C16 C15 C12 108.8(3) . . ?
C17 C15 C18 107.9(3) . . ?
C16 C15 C18 108.3(3) . . ?
C12 C15 C18 110.2(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.0(3) . . ?
C24 C19 C2 122.4(3) . . ?
C20 C19 C2 119.6(3) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 121.8(3) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 116.5(3) . . ?
C23 C22 C25 124.0(3) . . ?
C21 C22 C25 119.4(3) . . ?
C24 C23 C22 122.2(3) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C19 C24 C23 120.5(3) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C22 C25 C28 110.8(3) . . ?
C22 C25 C27 107.8(2) . . ?
C28 C25 C27 109.7(3) . . ?
C22 C25 C26 112.1(3) . . ?
C28 C25 C26 107.7(3) . . ?
C27 C25 C26 108.7(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O1 S1 O2 117.28(13) . . ?
O1 S1 C4 111.29(14) . . ?
O2 S1 C4 110.26(14) . . ?
O1 S1 C1 110.34(14) . . ?
O2 S1 C1 111.62(14) . . ?
C4 S1 C1 93.57(14) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.062
