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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_a40616a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O2 S'
_chemical_formula_weight         256.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.867(4)
_cell_length_b                   13.181(6)
_cell_length_c                   23.940(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2482.6(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2645
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      25.39

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12374
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.701
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2672
_reflns_number_gt                1872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0899P)²+0.9656P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2672
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1674
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15932(9) 0.27542(5) 0.16268(3) 0.0442(3) Uani 1 1 d . . . . .
O1 O 0.3231(3) 0.23155(16) 0.15203(8) 0.0610(6) Uani 1 1 d . . . . .
O2 O 0.0155(3) 0.20839(15) 0.16020(8) 0.0633(6) Uani 1 1 d . . . . .
C1 C 0.1564(3) 0.3457(2) 0.22562(10) 0.0426(6) Uani 1 1 d . . . . .
C2 C 0.1743(4) 0.3110(2) 0.27940(11) 0.0556(8) Uani 1 1 d . . . . .
H2 H 0.1935 0.2427 0.2867 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1627(4) 0.3813(2) 0.32253(13) 0.0607(9) Uani 1 1 d . . . . .
H3 H 0.1755 0.3602 0.3594 0.073 Uiso 1 1 calc R U . . .
C4 C 0.1322(4) 0.4825(2) 0.31096(12) 0.0595(8) Uani 1 1 d . . . . .
H4 H 0.1236 0.5284 0.3403 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1141(4) 0.5170(2) 0.25670(12) 0.0547(7) Uani 1 1 d . . . . .
H5 H 0.0936 0.5852 0.2495 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1272(4) 0.44755(19) 0.21302(10) 0.0435(6) Uani 1 1 d . . . . .
C7 C 0.1142(4) 0.4667(2) 0.15309(11) 0.0483(7) Uani 1 1 d . . . . .
H7 H 0.0971 0.5316 0.1389 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1282(3) 0.38581(18) 0.11965(10) 0.0399(6) Uani 1 1 d . . . . .
C9 C 0.1276(3) 0.37565(18) 0.05822(10) 0.0401(6) Uani 1 1 d . . . . .
C10 C 0.2144(3) 0.44528(19) 0.02384(10) 0.0417(6) Uani 1 1 d . . . . .
C11 C 0.2084(4) 0.4293(2) -0.03344(11) 0.0527(7) Uani 1 1 d . . . . .
H11 H 0.2640 0.4749 -0.0568 0.063 Uiso 1 1 calc R U . . .
C12 C 0.1230(4) 0.3484(2) -0.05717(12) 0.0570(8) Uani 1 1 d . . . . .
H12 H 0.1226 0.3398 -0.0957 0.068 Uiso 1 1 calc R U . . .
C13 C 0.0389(4) 0.2810(2) -0.02356(13) 0.0610(8) Uani 1 1 d . . . . .
H13 H -0.0199 0.2269 -0.0393 0.073 Uiso 1 1 calc R U . . .
C14 C 0.0414(4) 0.2935(2) 0.03361(12) 0.0519(7) Uani 1 1 d . . . . .
H14 H -0.0147 0.2470 0.0562 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3143(4) 0.5334(2) 0.04672(13) 0.0581(8) Uani 1 1 d . . . . .
H15A H 0.2378 0.5871 0.0567 0.087 Uiso 1 1 calc R U . . .
H15B H 0.3924 0.5572 0.0188 0.087 Uiso 1 1 calc R U . . .
H15C H 0.3763 0.5120 0.0792 0.087 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.435(2) . ?
S1 O2 1.437(2) . ?
S1 C1 1.769(3) . ?
S1 C8 1.799(3) . ?
C1 C2 1.374(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.460(4) . ?
C7 C8 1.338(3) . ?
C8 C9 1.477(4) . ?
C9 C14 1.406(4) . ?
C9 C10 1.409(3) . ?
C10 C11 1.388(4) . ?
C10 C15 1.505(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.368(4) . ?
C13 C14 1.379(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.86(14) . . ?
O1 S1 C1 111.96(12) . . ?
O2 S1 C1 110.31(12) . . ?
O1 S1 C8 110.27(12) . . ?
O2 S1 C8 111.50(13) . . ?
C1 S1 C8 93.57(12) . . ?
C2 C1 C6 122.7(2) . . ?
C2 C1 S1 128.5(2) . . ?
C6 C1 S1 108.78(18) . . ?
C1 C2 C3 117.8(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 121.5(3) . . ?
C4 C5 C6 118.8(3) . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 128.2(2) . . ?
C1 C6 C7 113.0(2) . . ?
C8 C7 C6 116.4(2) . . ?
C7 C8 C9 131.9(2) . . ?
C7 C8 S1 108.25(19) . . ?
C9 C8 S1 119.81(17) . . ?
C14 C9 C10 119.3(2) . . ?
C14 C9 C8 119.2(2) . . ?
C10 C9 C8 121.4(2) . . ?
C11 C10 C9 117.5(2) . . ?
C11 C10 C15 119.6(2) . . ?
C9 C10 C15 122.9(2) . . ?
C12 C11 C10 122.7(3) . . ?
C13 C12 C11 119.6(3) . . ?
C12 C13 C14 120.0(3) . . ?
C13 C14 C9 121.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 C2 -66.2(3) . . . . ?
O2 S1 C1 C2 65.7(3) . . . . ?
C8 S1 C1 C2 -179.8(3) . . . . ?
O1 S1 C1 C6 115.4(2) . . . . ?
O2 S1 C1 C6 -112.6(2) . . . . ?
C8 S1 C1 C6 1.9(2) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
S1 C1 C2 C3 -178.2(2) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
S1 C1 C6 C5 177.9(2) . . . . ?
C2 C1 C6 C7 179.4(3) . . . . ?
S1 C1 C6 C7 -2.1(3) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C1 C6 C7 C8 1.3(4) . . . . ?
C6 C7 C8 C9 -177.7(3) . . . . ?
C6 C7 C8 S1 0.2(3) . . . . ?
O1 S1 C8 C7 -116.2(2) . . . . ?
O2 S1 C8 C7 112.3(2) . . . . ?
C1 S1 C8 C7 -1.2(2) . . . . ?
O1 S1 C8 C9 62.0(2) . . . . ?
O2 S1 C8 C9 -69.6(2) . . . . ?
C1 S1 C8 C9 177.0(2) . . . . ?
C7 C8 C9 C14 -140.1(3) . . . . ?
S1 C8 C9 C14 42.3(3) . . . . ?
C7 C8 C9 C10 41.3(4) . . . . ?
S1 C8 C9 C10 -136.3(2) . . . . ?
C14 C9 C10 C11 0.7(4) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C14 C9 C10 C15 -178.1(3) . . . . ?
C8 C9 C10 C15 0.6(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C15 C10 C11 C12 178.2(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C9 0.8(5) . . . . ?
C10 C9 C14 C13 -0.8(4) . . . . ?
C8 C9 C14 C13 -179.5(3) . . . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2



_database_code_depnum_ccdc_archive 'CCDC 1011150'
