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

data_17080202
_audit_creation_date              2017-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_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. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C12 H10 O2 S'
_chemical_formula_sum             'C12 H10 O2 S'
_chemical_formula_weight          218.26
_chemical_melting_point           ?
_chemical_oxdiff_formula          CHONS
_chemical_oxdiff_usercomment      SPZ
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                    12.0982(2)
_cell_length_b                    7.66810(10)
_cell_length_c                    11.24180(10)
_cell_angle_alpha                 90
_cell_angle_beta                  96.7340(10)
_cell_angle_gamma                 90
_cell_volume                      1035.71(2)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     9463
_cell_measurement_temperature     150.00(10)
_cell_measurement_theta_max       73.9240
_cell_measurement_theta_min       6.8280
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     2.573
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.43446
_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     1.400
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        needle
_exptl_crystal_F_000              456
_exptl_crystal_size_max           0.400
_exptl_crystal_size_mid           0.050
_exptl_crystal_size_min           0.030
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0449
_diffrn_reflns_av_unetI/netI      0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_number             15305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full         67.684
_diffrn_reflns_theta_max          74.119
_diffrn_reflns_theta_min          3.679
_diffrn_ambient_environment       N~2~
_diffrn_ambient_temperature       150.00(10)
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  5.2913
_diffrn_detector_type             AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -50.00 -17.00   1.00    1.00    --  -41.89 -57.00 120.00   33
  2  ω     24.00  98.00   1.00    1.00    --   41.89-125.00   0.00   74
  3  ω     38.00 104.00   1.00    3.51    --  107.79 -94.00 -30.00   66
  4  ω     33.00 105.00   1.00    3.51    --  107.79 -94.00-120.00   72
  5  ω     25.00 109.00   1.00    3.51    --  107.79 -94.00  60.00   84
  6  ω     33.00 105.00   1.00    3.51    --  107.79 -94.00 150.00   72
  7  ω     81.00 113.00   1.00    3.51    --  107.79  61.00  30.00   32
  8  ω    114.00 177.00   1.00    3.51    --  107.79  77.00 -30.00   63
  9  ω    149.00 177.00   1.00    3.51    --  107.79  77.00-120.00   28
 10  ω    141.00 167.00   1.00    3.51    --  107.79  61.00-120.00   26
 11  ω    118.00 171.00   1.00    3.51    --  107.79  77.00-150.00   53
 12  ω    104.00 131.00   1.00    1.00    --   66.00  77.00-119.47   27
 13  ω     95.00 139.00   1.00    1.00    --   66.00  77.00-169.81   44
 14  ω     79.00 158.00   1.00    3.51    --  107.79  61.00 -90.00   79
 15  ω     96.00 142.00   1.00    1.00    --   66.00  77.00  11.56   46
 16  ω    110.00 139.00   1.00    1.00    --   66.00  75.00  50.62   29
 17  ω    116.00 142.00   1.00    1.00    --   66.00  77.00  83.95   26
 18  ω    106.00 133.00   1.00    1.00    --   66.00  77.00 131.34   27
 19  ω    130.00 177.00   1.00    3.51    --  107.79  77.00 150.00   47
 20  ω    117.00 175.00   1.00    3.51    --  107.79  77.00 120.00   58
 21  ω     85.00 112.00   1.00    3.51    --  107.79  61.00 -30.00   27
 22  ω     80.00 106.00   1.00    3.51    --  107.79  61.00 -60.00   26
 23  ω     80.00 178.00   1.00    3.51    --  107.79  77.00 -60.00   98
 24  ω     79.00 123.00   1.00    3.51    --  107.79  61.00-180.00   44
 25  ω     83.00 112.00   1.00    3.51    --  107.79  61.00-120.00   29
 26  ω     75.00 144.00   1.00    3.51    --  107.79  77.00-180.00   69
 27  ω     75.00 102.00   1.00    3.51    --  107.79  77.00-120.00   27
 28  ω     75.00 101.00   1.00    3.51    --  107.79  77.00-150.00   26
 29  ω     76.00 111.00   1.00    3.51    --  107.79  77.00 -30.00   35
 30  ω     76.00 144.00   1.00    3.51    --  107.79  77.00   0.00   68
 31  ω     76.00 140.00   1.00    3.51    --  107.79  77.00  90.00   64
 32  ω     80.00 106.00   1.00    3.51    --  107.79  61.00 150.00   26
 33  ω     75.00 100.00   1.00    3.51    --  107.79  77.00 120.00   25
 34  ω     76.00 104.00   1.00    3.51    --  107.79  77.00 150.00   28
 35  ω     75.00 176.00   1.00    3.51    --  107.79  77.00  60.00  101
 36  ω     75.00 173.00   1.00    3.51    --  107.79  77.00  30.00   98
 37  ω     36.00  67.00   1.00    1.00    --   66.00  77.00 131.34   31
 38  ω     33.00  64.00   1.00    1.00    --   66.00  77.00  83.95   31
 39  ω     34.00  70.00   1.00    1.00    --   66.00  75.00  50.62   36
 40  ω     30.00  60.00   1.00    1.00    --   62.00  77.00 -23.89   30
 41  ω     33.00  64.00   1.00    1.00    --   66.00  77.00  11.56   31
 42  ω     30.00  59.00   1.00    1.00    --   62.00  77.00 -79.19   29
 43  ω     34.00  65.00   1.00    1.00    --   66.00  77.00-119.47   31
 44  ω     34.00  64.00   1.00    1.00    --   66.00  77.00-169.81   30
 45  ω     12.00  37.00   1.00    1.00    --   46.00  84.00-115.53   25
 46  ω      0.00  33.00   1.00    1.00    --   34.00  84.00-146.97   33
 47  ω   -111.00 -18.00   1.00    1.00    --  -41.89 -37.00 -30.00   93
 48  ω    -59.00 -20.00   1.00    1.00    --  -41.89 -37.00-150.00   39
 49  ω      6.00  31.00   1.00    1.00    --   42.00  88.00  24.98   25
 50  ω     16.00  45.00   1.00    1.00    --   50.00  82.00 -35.19   29
 51  ω     20.00  45.00   1.00    1.00    --   54.00  81.00 121.33   25
 52  ω     20.00  45.00   1.00    1.00    --   54.00  81.00 177.50   25
 53  ω     14.00  39.00   1.00    1.00    --   46.00  80.00 132.31   25
 54  ω    -74.00   4.00   1.00    1.00    --  -41.89  77.00 150.00   78
 55  ω   -115.00 -52.00   1.00    1.00    --  -41.89 -57.00 120.00   63
 56  ω   -112.00 -81.00   1.00    1.00    --  -41.89 -37.00-150.00   31
;
_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       -0.0603200000
_diffrn_orient_matrix_UB_12       -0.1543930000
_diffrn_orient_matrix_UB_13       -0.0670272000
_diffrn_orient_matrix_UB_21       -0.0077591000
_diffrn_orient_matrix_UB_22       0.1041359000
_diffrn_orient_matrix_UB_23       -0.1178777000
_diffrn_orient_matrix_UB_31       0.1128974000
_diffrn_orient_matrix_UB_32       -0.0753404000
_diffrn_orient_matrix_UB_33       -0.0255337000
_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                 1942
_reflns_number_total              2084
_reflns_odcompleteness_completeness 100.00
_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     'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max          0.258
_refine_diff_density_min          -0.375
_refine_diff_density_rms          0.045
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.083
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      136
_refine_ls_number_reflns          2084
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0327
_refine_ls_R_factor_gt            0.0309
_refine_ls_restrained_S_all       1.083
_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)+(0.0420P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0819
_refine_ls_wR_factor_ref          0.0833
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      direct
_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
 S1 S 0.24240(3) 0.14954(4) 0.17291(3) 0.02335(12) Uani 1 1 d . . . . .
 C1 C 0.38298(11) 0.15795(16) 0.14373(11) 0.0203(3) Uani 1 1 d . . . . .
 C2 C 0.17974(11) -0.00303(17) 0.06824(11) 0.0208(3) Uani 1 1 d . . . . .
 O3 O 0.23945(9) 0.07951(16) 0.29145(9) 0.0346(3) Uani 1 1 d . . . . .
 O4 O 0.19369(9) 0.31802(14) 0.14429(11) 0.0339(3) Uani 1 1 d . . . . .
 C5 C 0.57315(12) 0.07558(18) 0.19573(14) 0.0296(3) Uani 1 1 d . . . . .
 H5 H 0.6278 0.0168 0.2454 0.036 Uiso 1 1 calc R . . . .
 C6 C 0.60180(12) 0.17202(19) 0.09992(13) 0.0274(3) Uani 1 1 d . . . . .
 H6 H 0.6759 0.1782 0.0856 0.033 Uiso 1 1 calc R . . . .
 C7 C 0.09293(12) -0.0694(2) -0.12830(13) 0.0290(3) Uani 1 1 d . . . . .
 H7 H 0.0655 -0.0347 -0.2054 0.035 Uiso 1 1 calc R . . . .
 C8 C 0.13908(11) 0.05275(18) -0.04638(12) 0.0248(3) Uani 1 1 d . . . . .
 H8 H 0.1428 0.1697 -0.0675 0.030 Uiso 1 1 calc R . . . .
 C9 C 0.17584(12) -0.17749(18) 0.10141(13) 0.0257(3) Uani 1 1 d . . . . .
 H9 H 0.2044 -0.2129 0.1780 0.031 Uiso 1 1 calc R . . . .
 C10 C 0.52076(12) 0.25951(19) 0.02510(12) 0.0281(3) Uani 1 1 d . . . . .
 H10 H 0.5407 0.3221 -0.0400 0.034 Uiso 1 1 calc R . . . .
 C11 C 0.41048(12) 0.25423(18) 0.04667(12) 0.0253(3) Uani 1 1 d . . . . .
 H11 H 0.3560 0.3138 -0.0027 0.030 Uiso 1 1 calc R . . . .
 C12 C 0.46279(12) 0.06660(18) 0.21770(12) 0.0255(3) Uani 1 1 d . . . . .
 H12 H 0.4426 0.0004 0.2810 0.031 Uiso 1 1 calc R . . . .
 C13 C 0.08740(12) -0.2433(2) -0.09598(14) 0.0311(3) Uani 1 1 d . . . . .
 H13 H 0.0557 -0.3242 -0.1515 0.037 Uiso 1 1 calc R . . . .
 C14 C 0.12859(13) -0.29785(19) 0.01823(14) 0.0308(3) Uani 1 1 d . . . . .
 H14 H 0.1246 -0.4148 0.0391 0.037 Uiso 1 1 calc R . . . .


_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 C1 1.7706(14) . ?
 S1 C2 1.7660(13) . ?
 S1 O3 1.4411(11) . ?
 S1 O4 1.4406(11) . ?
 C1 C11 1.3898(19) . ?
 C1 C12 1.3879(19) . ?
 C2 C8 1.3917(18) . ?
 C2 C9 1.3910(19) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.384(2) . ?
 C5 C12 1.388(2) . ?
 C6 H6 0.9300 . ?
 C6 C10 1.388(2) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.385(2) . ?
 C7 C13 1.385(2) . ?
 C8 H8 0.9300 . ?
 C9 H9 0.9300 . ?
 C9 C14 1.388(2) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.384(2) . ?
 C11 H11 0.9300 . ?
 C12 H12 0.9300 . ?
 C13 H13 0.9300 . ?
 C13 C14 1.386(2) . ?
 C14 H14 0.9300 . ?

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 S1 C1 104.32(6) . . ?
 O3 S1 C1 108.27(6) . . ?
 O3 S1 C2 108.30(6) . . ?
 O4 S1 C1 107.61(6) . . ?
 O4 S1 C2 108.23(6) . . ?
 O4 S1 O3 119.13(7) . . ?
 C11 C1 S1 119.24(10) . . ?
 C12 C1 S1 119.11(10) . . ?
 C12 C1 C11 121.65(13) . . ?
 C8 C2 S1 119.40(10) . . ?
 C9 C2 S1 118.94(10) . . ?
 C9 C2 C8 121.62(13) . . ?
 C6 C5 H5 120.0 . . ?
 C6 C5 C12 119.94(13) . . ?
 C12 C5 H5 120.0 . . ?
 C5 C6 H6 119.8 . . ?
 C5 C6 C10 120.43(14) . . ?
 C10 C6 H6 119.8 . . ?
 C8 C7 H7 119.8 . . ?
 C8 C7 C13 120.32(13) . . ?
 C13 C7 H7 119.8 . . ?
 C2 C8 H8 120.7 . . ?
 C7 C8 C2 118.62(13) . . ?
 C7 C8 H8 120.7 . . ?
 C2 C9 H9 120.6 . . ?
 C14 C9 C2 118.88(13) . . ?
 C14 C9 H9 120.6 . . ?
 C6 C10 H10 119.8 . . ?
 C11 C10 C6 120.45(13) . . ?
 C11 C10 H10 119.8 . . ?
 C1 C11 H11 120.7 . . ?
 C10 C11 C1 118.52(13) . . ?
 C10 C11 H11 120.7 . . ?
 C1 C12 H12 120.5 . . ?
 C5 C12 C1 118.99(13) . . ?
 C5 C12 H12 120.5 . . ?
 C7 C13 H13 119.7 . . ?
 C7 C13 C14 120.67(13) . . ?
 C14 C13 H13 119.7 . . ?
 C9 C14 H14 120.1 . . ?
 C13 C14 C9 119.87(14) . . ?
 C13 C14 H14 120.1 . . ?

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
 S1 C1 C11 C10 179.98(10) . . . . ?
 S1 C1 C12 C5 -179.02(10) . . . . ?
 S1 C2 C8 C7 178.28(10) . . . . ?
 S1 C2 C9 C14 -178.71(10) . . . . ?
 C1 S1 C2 C8 -85.84(12) . . . . ?
 C1 S1 C2 C9 91.93(12) . . . . ?
 C2 S1 C1 C11 78.51(11) . . . . ?
 C2 S1 C1 C12 -100.80(11) . . . . ?
 C2 C9 C14 C13 0.7(2) . . . . ?
 O3 S1 C1 C11 -166.30(11) . . . . ?
 O3 S1 C1 C12 14.38(12) . . . . ?
 O3 S1 C2 C8 159.00(11) . . . . ?
 O3 S1 C2 C9 -23.23(13) . . . . ?
 O4 S1 C1 C11 -36.31(12) . . . . ?
 O4 S1 C1 C12 144.38(11) . . . . ?
 O4 S1 C2 C8 28.54(13) . . . . ?
 O4 S1 C2 C9 -153.69(11) . . . . ?
 C5 C6 C10 C11 1.2(2) . . . . ?
 C6 C5 C12 C1 -1.2(2) . . . . ?
 C6 C10 C11 C1 -0.7(2) . . . . ?
 C7 C13 C14 C9 0.1(2) . . . . ?
 C8 C2 C9 C14 -1.0(2) . . . . ?
 C8 C7 C13 C14 -0.5(2) . . . . ?
 C9 C2 C8 C7 0.6(2) . . . . ?
 C11 C1 C12 C5 1.7(2) . . . . ?
 C12 C1 C11 C10 -0.7(2) . . . . ?
 C12 C5 C6 C10 -0.3(2) . . . . ?
 C13 C7 C8 C2 0.2(2) . . . . ?

_shelx_SHELXL_version_number      '2014/7'

_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 2.478
_oxdiff_exptl_absorpt_empirical_full_min 0.496
