# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cxy0541_0m
_database_code_depnum_ccdc_archive 'CCDC 1878446'
loop_
_audit_author_name
_audit_author_address
'xiaoyong chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2018-11-12 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;
_audit_creation_date             2018-11-12
_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         'C16 H18 O2 S'
_chemical_formula_sum            'C16 H18 O2 S'
_chemical_formula_weight         274.36
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.712(4)
_cell_length_b                   15.280(13)
_cell_length_c                   8.280(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.192(15)
_cell_angle_gamma                90
_cell_volume                     700.6(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      2.534
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0964 before and 0.0493 after correction. The Ratio of minimum to maximum transmission is 0.9434. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14818
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.537
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3155
_reflns_number_total             3221
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1476 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.1530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0623
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_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 0.57656(7) 0.54363(3) 0.56451(5) 0.01358(12) Uani 1 1 d . . . . .
O1 O 0.5664(3) 0.60517(11) 0.69479(17) 0.0215(3) Uani 1 1 d . . . . .
O2 O 0.8086(2) 0.50824(10) 0.55725(17) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.1014(4) 0.69884(14) -0.1062(2) 0.0195(4) Uani 1 1 d . . . . .
H1A H -0.053508 0.671157 -0.142501 0.029 Uiso 1 1 calc GR . . . .
H1B H 0.197127 0.686049 -0.183751 0.029 Uiso 1 1 calc GR . . . .
H1C H 0.080136 0.760997 -0.100599 0.029 Uiso 1 1 calc GR . . . .
C2 C 0.2271(3) 0.66496(12) 0.0629(2) 0.0148(4) Uani 1 1 d . . . . .
C3 C 0.4412(4) 0.61809(12) 0.0859(2) 0.0151(4) Uani 1 1 d . . . . .
H3 H 0.512218 0.610766 -0.002904 0.018 Uiso 1 1 calc R . . . .
C4 C 0.5503(3) 0.58206(13) 0.2398(2) 0.0142(4) Uani 1 1 d . . . . .
H4 H 0.692947 0.550403 0.253875 0.017 Uiso 1 1 calc R . . . .
C5 C 0.4453(3) 0.59359(12) 0.3719(2) 0.0126(3) Uani 1 1 d . . . . .
C6 C 0.3849(3) 0.45506(13) 0.5876(2) 0.0135(4) Uani 1 1 d . . . . .
H6A H 0.426086 0.437681 0.703861 0.016 Uiso 1 1 calc R . . . .
H6B H 0.220051 0.476544 0.562004 0.016 Uiso 1 1 calc R . . . .
C7 C 0.3911(3) 0.37326(12) 0.4821(2) 0.0146(4) Uani 1 1 d . . . . .
H7 H 0.558711 0.352933 0.504526 0.018 Uiso 1 1 calc R . . . .
C8 C 0.3018(3) 0.38791(12) 0.2965(2) 0.0121(3) Uani 1 1 d . . . . .
C9 C 0.4337(4) 0.35604(13) 0.1887(2) 0.0161(4) Uani 1 1 d . . . . .
H9 H 0.579541 0.327498 0.231653 0.019 Uiso 1 1 calc R . . . .
C10 C 0.3504(4) 0.36635(13) 0.0184(2) 0.0185(4) Uani 1 1 d . . . . .
H10 H 0.439725 0.344095 -0.052341 0.022 Uiso 1 1 calc R . . . .
C11 C 0.1348(4) 0.40961(13) -0.0479(2) 0.0174(4) Uani 1 1 d . . . . .
H11 H 0.080457 0.417098 -0.162490 0.021 Uiso 1 1 calc R . . . .
C12 C 0.0832(3) 0.42982(12) 0.2287(2) 0.0144(4) Uani 1 1 d . . . . .
H12 H -0.008967 0.450244 0.299106 0.017 Uiso 1 1 calc R . . . .
C13 C 0.0008(4) 0.44163(13) 0.0583(2) 0.0169(4) Uani 1 1 d . . . . .
H13 H -0.143784 0.470900 0.015121 0.020 Uiso 1 1 calc R . . . .
C14 C 0.1286(4) 0.67824(13) 0.1997(3) 0.0171(4) Uani 1 1 d . . . . .
H14 H -0.011356 0.711377 0.186819 0.021 Uiso 1 1 calc R . . . .
C15 C 0.2357(3) 0.64293(13) 0.3537(2) 0.0156(4) Uani 1 1 d . . . . .
H15 H 0.168613 0.652024 0.443927 0.019 Uiso 1 1 calc R . . . .
C16 C 0.2408(4) 0.30147(13) 0.5386(3) 0.0211(4) Uani 1 1 d . . . . .
H16A H 0.078730 0.322079 0.527149 0.032 Uiso 1 1 calc GR . . . .
H16B H 0.311272 0.287115 0.653067 0.032 Uiso 1 1 calc GR . . . .
H16C H 0.238234 0.250324 0.470855 0.032 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 O1 1.4429(17) . ?
S1 O2 1.4463(17) . ?
S1 C5 1.761(2) . ?
S1 C6 1.780(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.501(3) . ?
C2 C3 1.389(3) . ?
C2 C14 1.397(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C15 1.391(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.530(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.513(3) . ?
C7 C16 1.535(3) . ?
C8 C9 1.389(3) . ?
C8 C12 1.393(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O1 S1 O2 118.69(9) . . ?
O1 S1 C5 107.95(11) . . ?
O1 S1 C6 106.04(10) . . ?
O2 S1 C5 108.39(9) . . ?
O2 S1 C6 108.32(11) . . ?
C5 S1 C6 106.88(9) . . ?
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 120.62(18) . . ?
C3 C2 C14 118.65(18) . . ?
C14 C2 C1 120.72(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.84(18) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.46(18) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 S1 119.38(15) . . ?
C4 C5 C15 120.80(17) . . ?
C15 C5 S1 119.81(14) . . ?
S1 C6 H6A 108.0 . . ?
S1 C6 H6B 108.0 . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 S1 117.29(13) . . ?
C7 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C6 C7 H7 108.0 . . ?
C6 C7 C16 108.47(16) . . ?
C8 C7 C6 114.20(16) . . ?
C8 C7 H7 108.0 . . ?
C8 C7 C16 109.91(16) . . ?
C16 C7 H7 108.0 . . ?
C9 C8 C7 119.97(17) . . ?
C9 C8 C12 118.45(18) . . ?
C12 C8 C7 121.53(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.65(19) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.54(18) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C13 119.42(18) . . ?
C13 C11 H11 120.3 . . ?
C8 C12 H12 119.4 . . ?
C13 C12 C8 121.15(17) . . ?
C13 C12 H12 119.4 . . ?
C11 C13 H13 120.1 . . ?
C12 C13 C11 119.77(19) . . ?
C12 C13 H13 120.1 . . ?
C2 C14 H14 119.5 . . ?
C15 C14 C2 121.07(18) . . ?
C15 C14 H14 119.5 . . ?
C5 C15 H15 120.5 . . ?
C14 C15 C5 119.10(17) . . ?
C14 C15 H15 120.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C5 C15 C14 -176.94(15) . . . . ?
S1 C6 C7 C8 -64.7(2) . . . . ?
S1 C6 C7 C16 172.36(14) . . . . ?
O1 S1 C5 C4 139.33(15) . . . . ?
O1 S1 C5 C15 -41.68(17) . . . . ?
O1 S1 C6 C7 -170.82(13) . . . . ?
O2 S1 C5 C4 9.57(19) . . . . ?
O2 S1 C5 C15 -171.44(15) . . . . ?
O2 S1 C6 C7 -42.40(16) . . . . ?
C1 C2 C3 C4 -176.04(18) . . . . ?
C1 C2 C14 C15 176.21(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C14 C15 C5 0.1(3) . . . . ?
C3 C2 C14 C15 -2.4(3) . . . . ?
C3 C4 C5 S1 177.12(14) . . . . ?
C3 C4 C5 C15 -1.9(3) . . . . ?
C4 C5 C15 C14 2.0(3) . . . . ?
C5 S1 C6 C7 74.20(16) . . . . ?
C6 S1 C5 C4 -106.97(17) . . . . ?
C6 S1 C5 C15 72.02(17) . . . . ?
C6 C7 C8 C9 133.12(18) . . . . ?
C6 C7 C8 C12 -49.6(2) . . . . ?
C7 C8 C9 C10 177.83(18) . . . . ?
C7 C8 C12 C13 -178.88(18) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C8 C12 C13 C11 1.4(3) . . . . ?
C9 C8 C12 C13 -1.5(3) . . . . ?
C9 C10 C11 C13 -0.9(3) . . . . ?
C10 C11 C13 C12 -0.2(3) . . . . ?
C12 C8 C9 C10 0.5(3) . . . . ?
C14 C2 C3 C4 2.6(3) . . . . ?
C16 C7 C8 C9 -104.7(2) . . . . ?
C16 C7 C8 C12 72.6(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
