# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_dth-7-64b
_database_code_depnum_ccdc_archive 'CCDC 2270018'
loop_
_audit_author_name
_audit_author_address
'Benjamin S Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_audit_creation_date             2020-08-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 O S'
_chemical_formula_sum            'C13 H10 O S'
_chemical_formula_weight         214.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.0610(5)
_cell_length_b                   7.6912(5)
_cell_length_c                   21.2829(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     992.13(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5230
_cell_measurement_temperature    173
_cell_measurement_theta_max      66.671
_cell_measurement_theta_min      4.154
_shelx_estimated_absorpt_T_max   0.858
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    2.600
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0592 before and 0.0398 after correction. The Ratio of minimum to maximum transmission is 0.8746. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.061
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6117
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.666
_diffrn_reflns_theta_max         66.666
_diffrn_reflns_theta_min         4.154
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1719
_reflns_number_total             1751
_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       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_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         0.391
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.5278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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
S1 S 0.92923(12) 0.11327(10) 0.62973(3) 0.0251(2) Uani 1 1 d . . . . .
O1 O 0.7794(4) -0.0311(3) 0.61079(11) 0.0340(6) Uani 1 1 d . . . . .
C1 C 0.8360(5) 0.1897(4) 0.70461(14) 0.0250(7) Uani 1 1 d . . . . .
C2 C 0.9647(6) 0.1544(4) 0.75706(16) 0.0300(7) Uani 1 1 d . . . . .
H2 H 1.102887 0.097389 0.752758 0.036 Uiso 1 1 calc R . . . .
C3 C 0.8878(6) 0.2038(4) 0.81605(15) 0.0348(8) Uani 1 1 d . . . . .
H3 H 0.973936 0.182361 0.852528 0.042 Uiso 1 1 calc R . . . .
C4 C 0.6841(7) 0.2848(4) 0.82095(16) 0.0369(8) Uani 1 1 d . . . . .
H4 H 0.630623 0.317994 0.861162 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5580(6) 0.3180(4) 0.76849(15) 0.0321(7) Uani 1 1 d . . . . .
H5 H 0.418641 0.372973 0.773120 0.039 Uiso 1 1 calc R . . . .
C6 C 0.6311(5) 0.2725(4) 0.70906(15) 0.0259(7) Uani 1 1 d . . . . .
C7 C 0.4986(5) 0.3100(4) 0.65034(15) 0.0285(7) Uani 1 1 d . . . . .
H7A H 0.423621 0.202157 0.636571 0.034 Uiso 1 1 calc R . . . .
H7B H 0.383559 0.397201 0.660184 0.034 Uiso 1 1 calc R . . . .
C8 C 0.6400(5) 0.3768(4) 0.59774(15) 0.0261(6) Uani 1 1 d . . . . .
C9 C 0.5752(6) 0.5119(4) 0.55876(15) 0.0301(7) Uani 1 1 d . . . . .
H9 H 0.435310 0.565011 0.564954 0.036 Uiso 1 1 calc R . . . .
C10 C 0.7116(6) 0.5710(4) 0.51075(16) 0.0341(8) Uani 1 1 d . . . . .
H10 H 0.663591 0.663554 0.484559 0.041 Uiso 1 1 calc R . . . .
C11 C 0.9157(6) 0.4967(4) 0.50071(15) 0.0317(7) Uani 1 1 d . . . . .
H11 H 1.008950 0.538839 0.468210 0.038 Uiso 1 1 calc R . . . .
C12 C 0.9837(5) 0.3596(4) 0.53863(15) 0.0276(7) Uani 1 1 d . . . . .
H12 H 1.122939 0.306113 0.531916 0.033 Uiso 1 1 calc R . . . .
C13 C 0.8465(5) 0.3018(4) 0.58628(14) 0.0236(6) Uani 1 1 d . . . . .


_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 1.490(2) . ?
S1 C1 1.790(3) . ?
S1 C13 1.791(3) . ?
C1 C2 1.388(5) . ?
C1 C6 1.399(4) . ?
C2 C3 1.392(5) . ?
C3 C4 1.387(6) . ?
C4 C5 1.377(5) . ?
C5 C6 1.385(4) . ?
C6 C7 1.513(5) . ?
C7 C8 1.500(4) . ?
C8 C9 1.387(5) . ?
C8 C13 1.400(4) . ?
C9 C10 1.391(5) . ?
C10 C11 1.379(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.385(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 C1 107.05(14) . . ?
O1 S1 C13 107.02(14) . . ?
C1 S1 C13 96.06(14) . . ?
C2 C1 S1 118.3(3) . . ?
C2 C1 C6 122.2(3) . . ?
C6 C1 S1 119.3(2) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C3 C2 119.2(3) . . ?
C5 C4 C3 121.1(3) . . ?
C4 C5 C6 121.1(3) . . ?
C1 C6 C7 120.1(3) . . ?
C5 C6 C1 117.4(3) . . ?
C5 C6 C7 122.4(3) . . ?
C8 C7 C6 112.2(3) . . ?
C9 C8 C7 122.8(3) . . ?
C9 C8 C13 117.3(3) . . ?
C13 C8 C7 120.0(3) . . ?
C8 C9 C10 121.1(3) . . ?
C11 C10 C9 120.8(3) . . ?
C10 C11 C12 119.3(3) . . ?
C13 C12 C11 119.4(3) . . ?
C8 C13 S1 119.6(2) . . ?
C12 C13 S1 118.1(2) . . ?
C12 C13 C8 122.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
