# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_20200822li_znz6233_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2026143'
loop_
_audit_author_name
_audit_author_address
'Shiwen Liu'
;Yancheng Institute of Technology
China
;
_audit_update_record             
;
2020-08-30 deposited with the CCDC.	2020-09-27 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O S'
_chemical_formula_sum            'C18 H18 O S'
_chemical_formula_weight         282.38
_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'
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'

_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                   8.5247(14)
_cell_length_b                   21.621(3)
_cell_length_c                   9.2060(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.939(4)
_cell_angle_gamma                90
_cell_volume                     1525.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3021
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8419.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13345
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.635
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2246
_reflns_number_total             3504
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.026
_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)+(0.0493P)²+0.5896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1409
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C -0.3270(4) 0.41462(13) 0.1060(4) 0.0619(8) Uani 1 1 d . . . . .
H1A H -0.307063 0.425154 0.014139 0.093 Uiso 1 1 calc GR . . . .
H1B H -0.438570 0.394853 0.070153 0.093 Uiso 1 1 calc GR . . . .
H1C H -0.237216 0.386958 0.174976 0.093 Uiso 1 1 calc GR . . . .
C2 C -0.3241(3) 0.47217(12) 0.1976(3) 0.0450(6) Uani 1 1 d . . . . .
C3 C -0.1645(3) 0.51141(11) 0.2634(3) 0.0376(6) Uani 1 1 d . . . . .
C4 C -0.0109(3) 0.49598(11) 0.2541(3) 0.0413(6) Uani 1 1 d . . . . .
H4 H -0.005361 0.459176 0.204249 0.050 Uiso 1 1 calc R . . . .
C5 C 0.1343(3) 0.53418(11) 0.3173(3) 0.0404(6) Uani 1 1 d . . . . .
H5 H 0.235879 0.523001 0.309820 0.048 Uiso 1 1 calc R . . . .
C6 C 0.1271(3) 0.58933(11) 0.3920(3) 0.0352(5) Uani 1 1 d . . . . .
C7 C -0.0261(3) 0.60488(12) 0.4017(3) 0.0433(6) Uani 1 1 d . . . . .
H7 H -0.032376 0.641706 0.451110 0.052 Uiso 1 1 calc R . . . .
C8 C -0.1687(3) 0.56631(12) 0.3389(3) 0.0426(6) Uani 1 1 d . . . . .
H8 H -0.269885 0.577349 0.347311 0.051 Uiso 1 1 calc R . . . .
C9 C 0.4781(3) 0.61251(11) 0.4496(3) 0.0373(6) Uani 1 1 d . . . . .
H9A H 0.521963 0.575809 0.515692 0.045 Uiso 1 1 calc R . . . .
H9B H 0.443571 0.601419 0.337614 0.045 Uiso 1 1 calc R . . . .
C10 C 0.6161(3) 0.66220(11) 0.5022(3) 0.0346(5) Uani 1 1 d . . . . .
C11 C 0.6138(3) 0.70496(12) 0.3970(3) 0.0427(6) Uani 1 1 d . . . . .
H11 H 0.699463 0.735339 0.436925 0.051 Uiso 1 1 calc R . . . .
C12 C 0.4889(4) 0.70960(14) 0.2218(3) 0.0647(9) Uani 1 1 d . . . . .
H12A H 0.552768 0.710384 0.158005 0.097 Uiso 1 1 calc GR . . . .
H12B H 0.421651 0.746873 0.203554 0.097 Uiso 1 1 calc GR . . . .
H12C H 0.412068 0.674530 0.191461 0.097 Uiso 1 1 calc GR . . . .
C13 C 0.7460(3) 0.66356(10) 0.6749(3) 0.0341(5) Uani 1 1 d . . . . .
C14 C 0.8966(3) 0.70009(11) 0.7281(3) 0.0409(6) Uani 1 1 d . . . . .
H14 H 0.917098 0.723506 0.653394 0.049 Uiso 1 1 calc R . . . .
C15 C 1.0151(3) 0.70213(12) 0.8888(3) 0.0455(6) Uani 1 1 d . . . . .
H15 H 1.113355 0.727177 0.921160 0.055 Uiso 1 1 calc R . . . .
C16 C 0.9890(4) 0.66730(12) 1.0018(3) 0.0473(7) Uani 1 1 d . . . . .
H16 H 1.069268 0.668446 1.110001 0.057 Uiso 1 1 calc R . . . .
C17 C 0.8427(4) 0.63091(12) 0.9523(3) 0.0468(7) Uani 1 1 d . . . . .
H17 H 0.823772 0.607507 1.027892 0.056 Uiso 1 1 calc R . . . .
C18 C 0.7226(3) 0.62859(11) 0.7907(3) 0.0397(6) Uani 1 1 d . . . . .
H18 H 0.625088 0.603254 0.759475 0.048 Uiso 1 1 calc R . . . .
O1 O -0.4517(3) 0.48714(9) 0.2166(3) 0.0595(5) Uani 1 1 d . . . . .
S1 S 0.29470(8) 0.64409(3) 0.47389(8) 0.0419(2) 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.497(4) . ?
C2 C3 1.489(3) . ?
C2 O1 1.218(3) . ?
C3 C4 1.390(3) . ?
C3 C8 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C7 1.389(3) . ?
C6 S1 1.752(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(3) . ?
C9 S1 1.807(2) . ?
C10 C11 1.333(3) . ?
C10 C13 1.489(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.498(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.400(3) . ?
C13 C18 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(3) . ?
C18 H18 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 119.3(2) . . ?
O1 C2 C1 120.4(2) . . ?
O1 C2 C3 120.3(2) . . ?
C4 C3 C2 123.8(2) . . ?
C8 C3 C2 118.3(2) . . ?
C8 C3 C4 118.0(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 S1 126.00(19) . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 S1 114.94(18) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 119.4 . . ?
C7 C8 C3 121.3(2) . . ?
C7 C8 H8 119.4 . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
C10 C9 S1 106.65(16) . . ?
S1 C9 H9A 110.4 . . ?
S1 C9 H9B 110.4 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 C13 122.0(2) . . ?
C13 C10 C9 117.9(2) . . ?
C10 C11 H11 116.3 . . ?
C10 C11 C12 127.3(2) . . ?
C12 C11 H11 116.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C10 121.6(2) . . ?
C18 C13 C10 121.2(2) . . ?
C18 C13 C14 117.1(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.5(2) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 121.0(2) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C6 S1 C9 106.15(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
