# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

data_18012503
_audit_creation_date              2018-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number      '2014/7'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C13 H12 O3 S'
_chemical_formula_sum             'C13 H12 O3 S'
_chemical_formula_weight          248.29
_chemical_melting_point           ?
_chemical_oxdiff_formula          CHOS
_chemical_oxdiff_usercomment      SPh-M
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'

_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.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_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                    13.9202(7)
_cell_length_b                    8.0462(4)
_cell_length_c                    11.3730(5)
_cell_angle_alpha                 90
_cell_angle_beta                  105.687(5)
_cell_angle_gamma                 90
_cell_volume                      1226.38(11)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     2049
_cell_measurement_temperature     290.00(10)
_cell_measurement_theta_max       73.7690
_cell_measurement_theta_min       6.3610
_shelx_estimated_absorpt_T_max    0.934
_shelx_estimated_absorpt_T_min    0.656
_exptl_absorpt_coefficient_mu     2.302
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.78126
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.345
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        plate
_exptl_crystal_F_000              520
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.03
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0233
_diffrn_reflns_av_unetI/netI      0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_number             3483
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full         67.684
_diffrn_reflns_theta_max          73.979
_diffrn_reflns_theta_min          6.416
_diffrn_ambient_environment       air
_diffrn_ambient_temperature       290.00(10)
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  5.2913
_diffrn_detector_type             AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -108.00 -20.00   1.00    4.00    --  -41.64 -37.00  60.00   88
  2  ω   -114.00 -32.00   1.00    4.00    --  -41.64 -37.00 150.00   82
  3  ω     80.00 174.00   1.00   16.00    --  107.79  30.00  90.00   94
  4  ω    104.00 171.00   1.00   16.00    --  107.79 125.00 -90.00   67
  5  ω     42.00 130.00   1.00   16.00    --  107.79 -45.00 -90.00   88
  6  ω     25.00 108.00   1.00   16.00    --  107.79 -94.00-150.00   83
;
_diffrn_measurement_device        'four-circle diffractometer'
_diffrn_measurement_device_type   'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       -0.1082755000
_diffrn_orient_matrix_UB_12       0.0584360000
_diffrn_orient_matrix_UB_13       -0.0536960000
_diffrn_orient_matrix_UB_21       0.0074035000
_diffrn_orient_matrix_UB_22       -0.0418129000
_diffrn_orient_matrix_UB_23       -0.1293995000
_diffrn_orient_matrix_UB_31       -0.0376827000
_diffrn_orient_matrix_UB_32       -0.1776015000
_diffrn_orient_matrix_UB_33       0.0129074000
_diffrn_radiation_monochromator   mirror
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            CuK\a
_diffrn_radiation_wavelength      1.54184
_diffrn_source                    'micro-focus sealed X-ray tube'
_diffrn_source_type               'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1904
_reflns_number_total              2335
_reflns_odcompleteness_completeness 97.63
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      66.97
_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.
;
_reflns_threshold_expression      'I > 2σ(I)'
_computing_cell_refinement        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction         'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2015)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.312
_refine_diff_density_min          -0.183
_refine_diff_density_rms          0.046
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.156
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      155
_refine_ls_number_reflns          2335
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0585
_refine_ls_R_factor_gt            0.0478
_refine_ls_restrained_S_all       1.156
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0558P)²+0.8864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1526
_refine_ls_wR_factor_ref          0.1597
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00H(H00H,H00I,H00J)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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
 S001 S 0.27746(6) 0.33478(11) 0.21484(7) 0.0581(3) Uani 1 1 d . . . . .
 O002 O 0.07517(18) 0.8474(3) 0.4266(2) 0.0668(6) Uani 1 1 d . . . . .
 O003 O 0.23210(19) 0.1781(3) 0.2274(3) 0.0796(8) Uani 1 1 d . . . . .
 O004 O 0.2815(2) 0.3890(4) 0.0957(2) 0.0790(8) Uani 1 1 d . . . . .
 C005 C 0.4011(2) 0.3307(3) 0.3101(3) 0.0473(6) Uani 1 1 d . . . . .
 C006 C 0.1234(2) 0.7365(4) 0.3741(3) 0.0507(7) Uani 1 1 d . . . . .
 C007 C 0.2171(2) 0.4896(4) 0.2766(3) 0.0512(7) Uani 1 1 d . . . . .
 C008 C 0.1647(2) 0.7728(4) 0.2788(3) 0.0551(7) Uani 1 1 d . . . . .
 H008 H 0.1611 0.8801 0.2476 0.066 Uiso 1 1 calc R . . . .
 C009 C 0.2110(2) 0.6487(4) 0.2308(3) 0.0543(7) Uani 1 1 d . . . . .
 H009 H 0.2384 0.6728 0.1668 0.065 Uiso 1 1 calc R . . . .
 C00A C 0.1781(2) 0.4537(4) 0.3747(3) 0.0578(8) Uani 1 1 d . . . . .
 H00A H 0.1839 0.3472 0.4077 0.069 Uiso 1 1 calc R . . . .
 C00B C 0.1314(2) 0.5763(4) 0.4219(3) 0.0594(8) Uani 1 1 d . . . . .
 H00B H 0.1047 0.5522 0.4866 0.071 Uiso 1 1 calc R . . . .
 C00C C 0.4238(3) 0.2334(4) 0.4136(3) 0.0625(8) Uani 1 1 d . . . . .
 H00C H 0.3748 0.1701 0.4341 0.075 Uiso 1 1 calc R . . . .
 C00D C 0.4727(3) 0.4259(4) 0.2798(3) 0.0624(8) Uani 1 1 d . . . . .
 H00D H 0.4562 0.4930 0.2107 0.075 Uiso 1 1 calc R . . . .
 C00E C 0.5930(3) 0.3233(5) 0.4557(3) 0.0680(9) Uani 1 1 d . . . . .
 H00E H 0.6583 0.3196 0.5049 0.082 Uiso 1 1 calc R . . . .
 C00F C 0.5208(3) 0.2318(5) 0.4859(3) 0.0734(10) Uani 1 1 d . . . . .
 H00F H 0.5372 0.1674 0.5564 0.088 Uiso 1 1 calc R . . . .
 C00G C 0.5696(3) 0.4207(5) 0.3532(4) 0.0729(10) Uani 1 1 d . . . . .
 H00G H 0.6189 0.4834 0.3329 0.087 Uiso 1 1 calc R . . . .
 C00H C 0.0694(3) 1.0153(5) 0.3838(4) 0.0762(10) Uani 1 1 d . . . . .
 H00H H 0.0355 1.0180 0.2982 0.114 Uiso 1 1 calc GR . . . .
 H00I H 0.1355 1.0593 0.3966 0.114 Uiso 1 1 calc GR . . . .
 H00J H 0.0332 1.0812 0.4278 0.114 Uiso 1 1 calc GR . . . .


_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
 S001 O003 1.434(3) . ?
 S001 O004 1.439(3) . ?
 S001 C005 1.769(3) . ?
 S001 C007 1.753(3) . ?
 O002 C006 1.349(4) . ?
 O002 C00H 1.430(4) . ?
 C005 C00C 1.378(4) . ?
 C005 C00D 1.372(4) . ?
 C006 C008 1.388(4) . ?
 C006 C00B 1.392(5) . ?
 C007 C009 1.376(4) . ?
 C007 C00A 1.396(4) . ?
 C008 H008 0.9300 . ?
 C008 C009 1.378(4) . ?
 C009 H009 0.9300 . ?
 C00A H00A 0.9300 . ?
 C00A C00B 1.369(4) . ?
 C00B H00B 0.9300 . ?
 C00C H00C 0.9300 . ?
 C00C C00F 1.378(5) . ?
 C00D H00D 0.9300 . ?
 C00D C00G 1.381(5) . ?
 C00E H00E 0.9300 . ?
 C00E C00F 1.362(5) . ?
 C00E C00G 1.369(5) . ?
 C00F H00F 0.9300 . ?
 C00G H00G 0.9300 . ?
 C00H H00H 0.9600 . ?
 C00H H00I 0.9600 . ?
 C00H H00J 0.9600 . ?

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
 O003 S001 O004 119.36(17) . . ?
 O003 S001 C005 107.72(16) . . ?
 O003 S001 C007 108.26(15) . . ?
 O004 S001 C005 107.62(15) . . ?
 O004 S001 C007 107.87(16) . . ?
 C007 S001 C005 105.12(13) . . ?
 C006 O002 C00H 117.6(3) . . ?
 C00C C005 S001 119.6(2) . . ?
 C00D C005 S001 119.2(2) . . ?
 C00D C005 C00C 121.2(3) . . ?
 O002 C006 C008 124.5(3) . . ?
 O002 C006 C00B 115.9(3) . . ?
 C008 C006 C00B 119.6(3) . . ?
 C009 C007 S001 119.8(2) . . ?
 C009 C007 C00A 119.8(3) . . ?
 C00A C007 S001 120.3(3) . . ?
 C006 C008 H008 120.2 . . ?
 C009 C008 C006 119.5(3) . . ?
 C009 C008 H008 120.2 . . ?
 C007 C009 C008 120.8(3) . . ?
 C007 C009 H009 119.6 . . ?
 C008 C009 H009 119.6 . . ?
 C007 C00A H00A 120.2 . . ?
 C00B C00A C007 119.5(3) . . ?
 C00B C00A H00A 120.2 . . ?
 C006 C00B H00B 119.7 . . ?
 C00A C00B C006 120.7(3) . . ?
 C00A C00B H00B 119.7 . . ?
 C005 C00C H00C 120.8 . . ?
 C005 C00C C00F 118.5(3) . . ?
 C00F C00C H00C 120.8 . . ?
 C005 C00D H00D 120.4 . . ?
 C005 C00D C00G 119.2(3) . . ?
 C00G C00D H00D 120.4 . . ?
 C00F C00E H00E 119.9 . . ?
 C00F C00E C00G 120.1(3) . . ?
 C00G C00E H00E 119.9 . . ?
 C00C C00F H00F 119.5 . . ?
 C00E C00F C00C 121.0(3) . . ?
 C00E C00F H00F 119.5 . . ?
 C00D C00G H00G 120.0 . . ?
 C00E C00G C00D 120.1(3) . . ?
 C00E C00G H00G 120.0 . . ?
 O002 C00H H00H 109.5 . . ?
 O002 C00H H00I 109.5 . . ?
 O002 C00H H00J 109.5 . . ?
 H00H C00H H00I 109.5 . . ?
 H00H C00H H00J 109.5 . . ?
 H00I C00H H00J 109.5 . . ?


_olex2_date_sample_data_collection 2018-01-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.702
