# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Science
# This journal is © The Royal Society of Chemistry and Owner Societies 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H12 O3 S'
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         296.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.0173(5)
_cell_length_b                   14.9931(14)
_cell_length_c                   18.012(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.897(7)
_cell_angle_gamma                90
_cell_volume                     1351.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1356
_cell_measurement_theta_min      2.2667
_cell_measurement_theta_max      20.8220
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       'rod shaped'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_T_max  0.7462

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'fine focus'
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8163
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_full        25.17
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20

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

_reflns_number_total             2393
_reflns_number_gt                1461
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1733
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         2393
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0864P)^2^+0.2274P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 V2011.4-1 (Bruker AXS)'
_computing_cell_refinement       'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1' -0.3340(2) 0.09500(7) 0.14127(6) 0.0576(4) Uani d . 1 . .
C C2' -0.0898(7) 0.0796(2) 0.2090(2) 0.0456(9) Uani d . 1 . .
H H2' -0.0518 0.0247 0.2313 0.055 Uiso calc R 1 . .
C C3' 0.0467(7) 0.1560(2) 0.22778(19) 0.0392(9) Uani d . 1 . .
C C4' -0.0565(8) 0.2276(2) 0.1839(2) 0.0527(10) Uani d . 1 . .
H H4' 0.0123 0.2851 0.188 0.063 Uiso calc R 1 . .
C C5' -0.2686(7) 0.2052(2) 0.13423(19) 0.0435(9) Uani d . 1 . .
H H5' -0.3609 0.2446 0.102 0.052 Uiso calc R 1 . .
C C1 0.7387(7) 0.0511(2) 0.4174(2) 0.0495(10) Uani d . 1 . .
H H1 0.8908 0.063 0.4482 0.059 Uiso calc R 1 . .
C C2 0.6402(8) -0.0378(2) 0.4107(2) 0.0521(10) Uani d . 1 . .
C C3 0.3858(8) -0.0513(3) 0.3640(2) 0.0586(11) Uani d . 1 . .
H H2 0.3939 -0.1088 0.3395 0.07 Uiso calc R 1 . .
H H3 0.2397 -0.0535 0.3965 0.07 Uiso calc R 1 . .
C C4 0.5531(7) 0.2753(2) 0.34134(19) 0.0398(8) Uani d . 1 . .
C C5 0.2658(7) 0.1658(2) 0.28426(19) 0.0386(8) Uani d . 1 . .
C C7 0.6229(8) 0.3645(2) 0.3439(2) 0.0483(10) Uani d . 1 . .
H H7 0.5325 0.4054 0.3126 0.058 Uiso calc R 1 . .
C C8 0.8277(8) 0.3919(2) 0.3933(2) 0.0507(10) Uani d . 1 . .
H H8 0.8745 0.4519 0.3951 0.061 Uiso calc R 1 . .
C C9 0.9666(7) 0.3319(2) 0.4405(2) 0.0448(9) Uani d . 1 . .
C C10 0.8972(7) 0.2437(2) 0.43612(19) 0.0433(9) Uani d . 1 . .
H H10 0.9908 0.2029 0.4668 0.052 Uiso calc R 1 . .
C C11 0.6875(7) 0.2126(2) 0.38634(18) 0.0378(8) Uani d . 1 . .
C C12 0.6121(7) 0.1189(2) 0.37900(19) 0.0395(9) Uani d . 1 . .
C C13 0.3956(7) 0.1010(2) 0.32557(19) 0.0397(8) Uani d . 1 . .
C C14 1.1884(8) 0.3629(3) 0.4950(2) 0.0583(11) Uani d . 1 . .
H H14B 1.1237 0.3664 0.5439 0.087 Uiso calc R 1 . .
H H14A 1.2485 0.4207 0.4805 0.087 Uiso calc R 1 . .
H H14C 1.3342 0.3214 0.4954 0.087 Uiso calc R 1 . .
O O3 0.7428(6) -0.10290(17) 0.44291(18) 0.0761(9) Uani d . 1 . .
O O4 0.3265(5) 0.01490(15) 0.30875(15) 0.0573(7) Uani d . 1 . .
O O6 0.3443(5) 0.25299(14) 0.29178(13) 0.0435(6) Uani d . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1' 0.0519(7) 0.0592(7) 0.0589(7) 0.0013(5) -0.0154(5) -0.0036(5)
C2' 0.046(2) 0.045(2) 0.044(2) 0.0033(17) -0.0063(18) 0.0026(17)
C3' 0.036(2) 0.040(2) 0.040(2) 0.0068(16) -0.0039(17) -0.0059(16)
C4' 0.058(3) 0.039(2) 0.058(2) 0.0067(18) -0.016(2) 0.0007(18)
C5' 0.048(2) 0.0344(19) 0.046(2) 0.0082(16) -0.0190(18) -0.0014(16)
C1 0.044(2) 0.043(2) 0.058(2) 0.0046(18) -0.0179(19) 0.0007(19)
C2 0.054(2) 0.044(2) 0.056(2) 0.0051(19) -0.012(2) 0.0059(19)
C3 0.059(3) 0.046(2) 0.068(3) -0.0050(19) -0.016(2) 0.010(2)
C4 0.039(2) 0.040(2) 0.038(2) 0.0029(16) -0.0065(17) -0.0041(16)
C5 0.041(2) 0.0355(19) 0.039(2) 0.0038(16) -0.0030(17) -0.0010(16)
C7 0.059(3) 0.039(2) 0.046(2) 0.0056(18) -0.006(2) 0.0019(17)
C8 0.061(3) 0.039(2) 0.052(2) -0.0109(19) 0.001(2) -0.0060(18)
C9 0.040(2) 0.051(2) 0.043(2) -0.0041(18) -0.0004(17) -0.0055(18)
C10 0.043(2) 0.044(2) 0.041(2) 0.0062(17) -0.0082(17) -0.0022(17)
C11 0.039(2) 0.0384(19) 0.0358(19) 0.0029(16) -0.0015(16) -0.0028(16)
C12 0.040(2) 0.0407(19) 0.037(2) 0.0027(16) -0.0030(16) -0.0001(16)
C13 0.042(2) 0.0362(19) 0.039(2) 0.0022(16) -0.0060(16) -0.0029(16)
C14 0.055(3) 0.061(3) 0.057(3) -0.013(2) -0.010(2) -0.011(2)
O3 0.084(2) 0.0456(17) 0.093(2) 0.0040(15) -0.0339(18) 0.0202(16)
O4 0.0668(18) 0.0347(14) 0.0661(18) -0.0001(12) -0.0281(14) 0.0029(13)
O6 0.0496(15) 0.0340(13) 0.0445(15) 0.0038(11) -0.0144(12) -0.0016(11)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1' C2' . 1.685(4) ?
S1' C5' . 1.690(3) ?
C2' C3' . 1.365(5) ?
C2' H2' . 0.93 ?
C3' C4' . 1.410(5) ?
C3' C5 . 1.454(5) ?
C4' C5' . 1.384(5) ?
C4' H4' . 0.93 ?
C5' H5' . 0.93 ?
C1 C12 . 1.362(5) ?
C1 C2 . 1.424(5) ?
C1 H1 . 0.93 ?
C2 O3 . 1.230(4) ?
C2 C3 . 1.494(5) ?
C3 O4 . 1.422(4) ?
C3 H2 . 0.97 ?
C3 H3 . 0.97 ?
C4 O6 . 1.371(4) ?
C4 C7 . 1.383(5) ?
C4 C11 . 1.386(5) ?
C5 C13 . 1.362(5) ?
C5 O6 . 1.369(4) ?
C7 C8 . 1.375(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.392(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.369(5) ?
C9 C14 . 1.506(5) ?
C10 C11 . 1.414(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.458(5) ?
C12 C13 . 1.427(5) ?
C13 O4 . 1.366(4) ?
C14 H14B . 0.96 ?
C14 H14A . 0.96 ?
C14 H14C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2' S1' C5' . . 93.01(17) ?
C3' C2' S1' . . 113.1(3) ?
C3' C2' H2' . . 123.5 ?
S1' C2' H2' . . 123.5 ?
C2' C3' C4' . . 109.9(3) ?
C2' C3' C5 . . 126.9(3) ?
C4' C3' C5 . . 123.2(3) ?
C5' C4' C3' . . 114.5(3) ?
C5' C4' H4' . . 122.7 ?
C3' C4' H4' . . 122.7 ?
C4' C5' S1' . . 109.5(3) ?
C4' C5' H5' . . 125.3 ?
S1' C5' H5' . . 125.3 ?
C12 C1 C2 . . 120.6(3) ?
C12 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
O3 C2 C1 . . 124.9(4) ?
O3 C2 C3 . . 118.2(3) ?
C1 C2 C3 . . 116.9(3) ?
O4 C3 C2 . . 115.5(3) ?
O4 C3 H2 . . 108.4 ?
C2 C3 H2 . . 108.4 ?
O4 C3 H3 . . 108.4 ?
C2 C3 H3 . . 108.4 ?
H2 C3 H3 . . 107.5 ?
O6 C4 C7 . . 116.0(3) ?
O6 C4 C11 . . 122.4(3) ?
C7 C4 C11 . . 121.7(3) ?
C13 C5 O6 . . 120.2(3) ?
C13 C5 C3' . . 128.4(3) ?
O6 C5 C3' . . 111.4(3) ?
C8 C7 C4 . . 119.1(3) ?
C8 C7 H7 . . 120.5 ?
C4 C7 H7 . . 120.5 ?
C7 C8 C9 . . 121.6(3) ?
C7 C8 H8 . . 119.2 ?
C9 C8 H8 . . 119.2 ?
C10 C9 C8 . . 118.3(3) ?
C10 C9 C14 . . 120.7(3) ?
C8 C9 C14 . . 121.1(3) ?
C9 C10 C11 . . 122.1(3) ?
C9 C10 H10 . . 119.0 ?
C11 C10 H10 . . 119.0 ?
C4 C11 C10 . . 117.3(3) ?
C4 C11 C12 . . 119.2(3) ?
C10 C11 C12 . . 123.5(3) ?
C1 C12 C13 . . 120.6(3) ?
C1 C12 C11 . . 124.3(3) ?
C13 C12 C11 . . 115.0(3) ?
C5 C13 O4 . . 116.6(3) ?
C5 C13 C12 . . 123.2(3) ?
O4 C13 C12 . . 119.8(3) ?
C9 C14 H14B . . 109.5 ?
C9 C14 H14A . . 109.5 ?
H14B C14 H14A . . 109.5 ?
C9 C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
C13 O4 C3 . . 117.8(3) ?
C5 O6 C4 . . 120.0(3) ?


_database_code_depnum_ccdc_archive 'CCDC 956397'