# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
# 
#######################################################################

data_hlj1027
_database_code_depnum_ccdc_archive 'CCDC 1881760'
loop_
_audit_author_name
_audit_author_address
'Yibiao Li'
;Wuyi University
China
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;
_audit_creation_date             2018-08-14
_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 H16 S'
_chemical_formula_sum            'C13 H16 S'
_chemical_formula_weight         204.32
_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 0.0033 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'
S S 0.1246 0.1234 '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                   12.8311(9)
_cell_length_b                   7.0802(5)
_cell_length_c                   12.0660(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.396(7)
_cell_angle_gamma                90
_cell_volume                     1096.13(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3463
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8340
_cell_measurement_theta_min      3.2650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7903
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.631
_diffrn_reflns_theta_min         3.175
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  11.00   1.00    1.00    --  -11.59 -57.00 150.00   90
  2  ω    -40.00  59.00   1.00    1.00    --  -11.59  57.00 -60.00   99
  3  ω    -12.00  77.00   1.00    1.00    --   11.74  77.00  60.00   89
;
_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      0.0016145000
_diffrn_orient_matrix_UB_12      0.0815348000
_diffrn_orient_matrix_UB_13      -0.0340413000
_diffrn_orient_matrix_UB_21      0.0108384000
_diffrn_orient_matrix_UB_22      -0.0574611000
_diffrn_orient_matrix_UB_23      -0.0466528000
_diffrn_orient_matrix_UB_31      -0.0542196000
_diffrn_orient_matrix_UB_32      -0.0090306000
_diffrn_orient_matrix_UB_33      -0.0108579000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2201
_reflns_number_total             2619
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.296
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.051
_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)+(0.0512P)²+0.2366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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 0.34886(3) 0.84743(6) 0.26626(3) 0.02113(14) Uani 1 1 d . . . . .
C1 C 0.24459(11) 0.4598(2) 0.37901(12) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.34009(11) 0.6130(2) 0.21794(12) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.19407(12) 0.6151(2) 0.42656(12) 0.0175(3) Uani 1 1 d . . . . .
H2 H 0.196500 0.730978 0.390381 0.021 Uiso 1 1 calc R . . . .
C7 C 0.29945(11) 0.4659(2) 0.27289(12) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.307330 0.349556 0.238194 0.022 Uiso 1 1 calc R . . . .
C3 C 0.14050(11) 0.6018(2) 0.52586(12) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.23843(12) 0.2879(2) 0.43574(13) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.269503 0.180920 0.405839 0.023 Uiso 1 1 calc R . . . .
C5 C 0.18676(12) 0.2748(2) 0.53574(13) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.185073 0.159431 0.572522 0.025 Uiso 1 1 calc R . . . .
C4 C 0.13733(11) 0.4298(2) 0.58251(12) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.41655(12) 0.9316(2) 0.14342(13) 0.0217(3) Uani 1 1 d . . . . .
H11A H 0.367816 0.987925 0.091236 0.026 Uiso 1 1 calc R . . . .
H11B H 0.468777 1.024944 0.163342 0.026 Uiso 1 1 calc R . . . .
C9 C 0.38851(13) 0.5977(2) 0.10423(13) 0.0216(3) Uani 1 1 d . . . . .
H9A H 0.335248 0.608603 0.047147 0.026 Uiso 1 1 calc R . . . .
H9B H 0.423018 0.476642 0.096012 0.026 Uiso 1 1 calc R . . . .
C10 C 0.46716(13) 0.7579(2) 0.09388(13) 0.0239(4) Uani 1 1 d . . . . .
H10A H 0.530857 0.727125 0.133701 0.029 Uiso 1 1 calc R . . . .
H10B H 0.483964 0.779618 0.016671 0.029 Uiso 1 1 calc R . . . .
C12 C 0.08531(12) 0.7733(2) 0.57145(13) 0.0228(4) Uani 1 1 d . . . . .
H12A H 0.119143 0.813092 0.638704 0.034 Uiso 1 1 calc GR . . . .
H12B H 0.014008 0.741955 0.586559 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.087697 0.873673 0.518062 0.034 Uiso 1 1 calc GR . . . .
C13 C 0.08050(13) 0.4096(3) 0.69059(13) 0.0256(4) Uani 1 1 d . . . . .
H13A H 0.110173 0.494239 0.744339 0.038 Uiso 1 1 calc GR . . . .
H13B H 0.086883 0.281979 0.716711 0.038 Uiso 1 1 calc GR . . . .
H13C H 0.008186 0.439525 0.679652 0.038 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
S1 C8 1.7628(16) . ?
S1 C11 1.8234(16) . ?
C1 C2 1.401(2) . ?
C1 C7 1.466(2) . ?
C1 C6 1.399(2) . ?
C8 C7 1.342(2) . ?
C8 C9 1.514(2) . ?
C2 C3 1.389(2) . ?
C3 C4 1.397(2) . ?
C3 C12 1.511(2) . ?
C6 C5 1.384(2) . ?
C5 C4 1.389(2) . ?
C4 C13 1.505(2) . ?
C11 C10 1.516(2) . ?
C9 C10 1.524(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
C8 S1 C11 93.94(7) . . ?
C2 C1 C7 124.09(14) . . ?
C6 C1 C2 117.03(14) . . ?
C6 C1 C7 118.84(14) . . ?
C7 C8 S1 126.26(12) . . ?
C7 C8 C9 123.76(14) . . ?
C9 C8 S1 109.96(11) . . ?
C3 C2 C1 122.23(15) . . ?
C8 C7 C1 130.18(14) . . ?
C2 C3 C4 119.82(14) . . ?
C2 C3 C12 119.73(14) . . ?
C4 C3 C12 120.45(14) . . ?
C5 C6 C1 120.93(15) . . ?
C6 C5 C4 121.60(15) . . ?
C3 C4 C13 121.52(15) . . ?
C5 C4 C3 118.35(14) . . ?
C5 C4 C13 120.12(15) . . ?
C10 C11 S1 105.24(11) . . ?
C8 C9 C10 107.29(13) . . ?
C11 C10 C9 106.63(13) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.140
_oxdiff_exptl_absorpt_empirical_full_min 0.668
