# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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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
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_dpsx02

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O S'
_chemical_formula_weight         240.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/c

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                   12.4853(3)
_cell_length_b                   7.2462(2)
_cell_length_c                   13.1368(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.118(2)
_cell_angle_gamma                90.00
_cell_volume                     1176.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    2.254
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3838
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.81
_diffrn_reflns_theta_max         71.99
_reflns_number_total             2248
_reflns_number_gt                2099
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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 > 2σ(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)+(0.0461P)²+0.7232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2248
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
S1 S 0.69616(3) 0.08732(6) 0.32752(3) 0.02266(14) Uani 1 1 d . . .
O1 O 0.48314(9) 0.04283(17) 0.21611(9) 0.0230(3) Uani 1 1 d . . .
H1O H 0.5364 0.0335 0.2601 0.035 Uiso 1 1 calc R . .
C6 C 0.41549(12) 0.1782(2) 0.05794(12) 0.0174(3) Uani 1 1 d . . .
C8 C 0.60985(12) 0.2170(2) 0.13692(12) 0.0178(3) Uani 1 1 d . . .
H8 H 0.6203 0.2847 0.0790 0.021 Uiso 1 1 calc R . .
C5 C 0.42884(12) 0.2559(2) -0.03668(12) 0.0204(3) Uani 1 1 d . . .
H5 H 0.4979 0.2838 -0.0508 0.024 Uiso 1 1 calc R . .
C14 C 0.97683(13) 0.4195(2) 0.25638(13) 0.0231(4) Uani 1 1 d . . .
H14 H 1.0239 0.4717 0.3098 0.028 Uiso 1 1 calc R . .
C7 C 0.50749(12) 0.1444(2) 0.13927(12) 0.0175(3) Uani 1 1 d . . .
C4 C 0.33985(13) 0.2916(2) -0.10967(13) 0.0235(4) Uani 1 1 d . . .
H4 H 0.3495 0.3427 -0.1727 0.028 Uiso 1 1 calc R . .
C2 C 0.22197(13) 0.1728(2) 0.00402(13) 0.0238(4) Uani 1 1 d . . .
H2 H 0.1527 0.1452 0.0177 0.029 Uiso 1 1 calc R . .
C13 C 1.00633(13) 0.4098(2) 0.15884(14) 0.0233(4) Uani 1 1 d . . .
H13 H 1.0739 0.4518 0.1473 0.028 Uiso 1 1 calc R . .
C10 C 0.80468(12) 0.2766(2) 0.19438(12) 0.0171(3) Uani 1 1 d . . .
C1 C 0.31072(13) 0.1350(2) 0.07720(12) 0.0211(3) Uani 1 1 d . . .
H1 H 0.3007 0.0807 0.1393 0.025 Uiso 1 1 calc R . .
C9 C 0.69963(12) 0.1974(2) 0.21448(12) 0.0176(3) Uani 1 1 d . . .
C15 C 0.87736(12) 0.3517(2) 0.27500(12) 0.0202(3) Uani 1 1 d . . .
H15 H 0.8589 0.3560 0.3411 0.024 Uiso 1 1 calc R . .
C3 C 0.23609(13) 0.2514(2) -0.08904(13) 0.0240(4) Uani 1 1 d . . .
H3 H 0.1764 0.2773 -0.1377 0.029 Uiso 1 1 calc R . .
C12 C 0.93455(13) 0.3370(2) 0.07819(13) 0.0225(3) Uani 1 1 d . . .
H12 H 0.9540 0.3310 0.0125 0.027 Uiso 1 1 calc R . .
C11 C 0.83361(12) 0.2733(2) 0.09582(12) 0.0192(3) Uani 1 1 d . . .
H11 H 0.7851 0.2281 0.0413 0.023 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0187(2) 0.0277(2) 0.0207(2) 0.00515(15) -0.00032(15) 0.00096(15)
O1 0.0170(5) 0.0288(6) 0.0229(6) 0.0049(5) 0.0013(4) -0.0026(5)
C6 0.0154(7) 0.0155(7) 0.0209(8) -0.0036(6) 0.0010(6) -0.0006(6)
C8 0.0162(7) 0.0172(7) 0.0194(7) 0.0010(6) 0.0005(6) 0.0001(6)
C5 0.0152(7) 0.0217(8) 0.0237(8) -0.0006(6) 0.0009(6) -0.0012(6)
C14 0.0171(8) 0.0186(8) 0.0307(9) -0.0017(6) -0.0070(7) 0.0001(6)
C7 0.0168(7) 0.0158(7) 0.0198(7) -0.0016(6) 0.0020(6) 0.0000(6)
C4 0.0220(8) 0.0230(8) 0.0241(8) 0.0023(7) -0.0012(6) -0.0009(6)
C2 0.0144(7) 0.0257(8) 0.0310(9) -0.0047(7) 0.0018(6) -0.0021(6)
C13 0.0147(7) 0.0208(8) 0.0335(9) 0.0031(7) 0.0003(6) -0.0019(6)
C10 0.0142(7) 0.0140(7) 0.0221(8) 0.0012(6) -0.0012(6) 0.0021(5)
C1 0.0180(7) 0.0236(8) 0.0216(8) -0.0023(6) 0.0027(6) -0.0038(6)
C9 0.0170(7) 0.0158(7) 0.0195(7) -0.0013(6) 0.0013(6) 0.0018(6)
C15 0.0182(7) 0.0185(8) 0.0223(8) -0.0002(6) -0.0025(6) 0.0028(6)
C3 0.0172(7) 0.0212(8) 0.0310(9) -0.0019(7) -0.0060(6) 0.0010(6)
C12 0.0192(8) 0.0232(8) 0.0246(8) 0.0029(6) 0.0017(6) -0.0001(6)
C11 0.0162(7) 0.0178(8) 0.0222(8) 0.0013(6) -0.0024(6) -0.0003(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.6915(16) . ?
O1 C7 1.3190(19) . ?
C6 C5 1.396(2) . ?
C6 C1 1.402(2) . ?
C6 C7 1.475(2) . ?
C8 C7 1.386(2) . ?
C8 C9 1.412(2) . ?
C5 C4 1.386(2) . ?
C14 C13 1.384(3) . ?
C14 C15 1.389(2) . ?
C4 C3 1.391(2) . ?
C2 C3 1.382(2) . ?
C2 C1 1.388(2) . ?
C13 C12 1.391(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.403(2) . ?
C10 C9 1.489(2) . ?
C12 C11 1.392(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
C5 C6 C1 118.84(14) . . ?
C5 C6 C7 122.24(14) . . ?
C1 C6 C7 118.90(14) . . ?
C7 C8 C9 125.90(15) . . ?
C4 C5 C6 120.45(14) . . ?
C13 C14 C15 120.43(15) . . ?
O1 C7 C8 122.79(14) . . ?
O1 C7 C6 114.01(13) . . ?
C8 C7 C6 123.17(14) . . ?
C5 C4 C3 120.25(15) . . ?
C3 C2 C1 120.33(15) . . ?
C14 C13 C12 119.82(15) . . ?
C11 C10 C15 118.91(14) . . ?
C11 C10 C9 120.58(14) . . ?
C15 C10 C9 120.50(14) . . ?
C2 C1 C6 120.31(15) . . ?
C8 C9 C10 117.57(14) . . ?
C8 C9 S1 124.40(12) . . ?
C10 C9 S1 118.02(11) . . ?
C14 C15 C10 120.21(15) . . ?
C2 C3 C4 119.80(15) . . ?
C11 C12 C13 120.00(15) . . ?
C12 C11 C10 120.58(14) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        71.99
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 974809'
