# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_tangshizhong1_0425_auto
_database_code_depnum_ccdc_archive 'CCDC 2168879'
loop_
_audit_author_name
_audit_author_address
'Shi-Zhong Tang'
;The University of LanZhou
China
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H15 N S'
_chemical_formula_sum            'C9 H15 N S'
_chemical_formula_weight         169.28
_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'
N N 0.0311 0.0180 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6856(3)
_cell_length_b                   9.2050(2)
_cell_length_c                   10.7124(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.687(3)
_cell_angle_gamma                90
_cell_volume                     924.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6904
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.9050
_cell_measurement_theta_min      4.8120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8401
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.532
_diffrn_reflns_theta_min         4.805
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  21.00   0.50    0.05    --   47.57 -19.00  90.00   78
  2  ω     38.00  63.00   0.50    0.07    --  107.75 -57.00 150.00   50
  3  ω     76.00 101.00   0.50    0.07    --  107.75 -77.00 120.00   50
  4  ω     36.00  61.00   0.50    0.07    --  107.75 -57.00-120.00   50
  5  ω    -26.00   4.00   0.50    0.05    --   47.57 -19.00-150.00   60
  6  ω     36.00 127.00   0.50    0.07    --  107.75-149.00  35.00  182
  7  ω     86.00 111.00   0.50    0.07    --  107.75-125.00-120.00   50
  8  ω     35.00  61.00   0.50    0.07    --  107.75-125.00-120.00   52
  9  ω     -8.00  21.00   0.50    0.05    --  -47.57  77.00 -60.00   58
 10  ω    -70.00 -30.00   0.50    0.05    --  -47.57  77.00 -60.00   80
 11  ω   -154.00 -98.00   0.50    0.07    -- -100.00 -17.00 -91.00  112
 12  ω   -100.00 -74.00   0.50    0.05    --  -47.57-149.00  35.00   52
 13  ω   -172.00 -89.00   0.50    0.07    -- -100.00-111.00 100.00  166
 14  ω     98.00 171.00   0.50    0.07    --  107.75 111.00-164.00  146
 15  ω    -91.00 -34.00   0.50    0.05    --  -47.57 125.00 -60.00  114
 16  ω    -17.00   9.00   0.50    0.05    --   47.57 -19.00 -30.00   52
 17  ω    -25.00  22.00   0.50    0.05    --   47.57 -19.00  60.00   94
 18  ω    -58.00 -31.00   0.50    0.07    -- -100.00  57.00  30.00   54
 19  ω    -62.00 -28.00   0.50    0.07    -- -100.00  57.00  60.00   68
 20  ω    -69.00 -44.00   0.50    0.07    -- -100.00  57.00   0.00   50
 21  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00 120.00   50
 22  ω     81.00 106.00   0.50    0.07    --  107.75 -99.00  90.00   50
 23  ω     84.00 110.00   0.50    0.07    --  107.75-125.00 -90.00   52
 24  ω     36.00  61.00   0.50    0.07    --  107.75 -57.00 -30.00   50
 25  ω     41.00 112.00   0.50    0.07    --  107.75-125.00  60.00  142
 26  ω     61.00  92.00   0.50    0.07    --  107.75-125.00 150.00   62
 27  ω     35.00  60.00   0.50    0.07    --  107.75 -57.00 -90.00   50
 28  ω     85.00 128.00   0.50    0.07    --  107.75 123.00 -80.00   86
 29  ω      3.00  34.00   0.50    0.05    --   47.57 -37.00 120.00   62
 30  ω    -20.00   7.00   0.50    0.05    --   47.57 -19.00   0.00   54
 31  ω    -11.00  15.00   0.50    0.05    --   47.57 -19.00 -90.00   52
 32  ω    -65.00 -32.00   0.50    0.07    -- -100.00  57.00 150.00   66
 33  ω    -60.00 -28.00   0.50    0.07    -- -100.00  57.00 -90.00   64
 34  ω    -55.00 -29.00   0.50    0.07    -- -100.00  57.00   0.00   52
 35  ω   -111.00 -85.00   0.50    0.07    -- -100.00 125.00-180.00   52
 36  ω    138.00 174.00   0.50    0.07    --  107.75  57.00-120.00   72
 37  ω     77.00 103.00   0.50    0.07    --  107.75 -77.00-150.00   52
 38  ω    133.00 162.00   0.50    0.07    --  107.75 123.00 -80.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1006381000
_diffrn_orient_matrix_UB_12      -0.0861150000
_diffrn_orient_matrix_UB_13      0.0381870000
_diffrn_orient_matrix_UB_21      0.0477060000
_diffrn_orient_matrix_UB_22      -0.1427155000
_diffrn_orient_matrix_UB_23      -0.0395967000
_diffrn_orient_matrix_UB_31      0.1208104000
_diffrn_orient_matrix_UB_32      -0.0152759000
_diffrn_orient_matrix_UB_33      0.1544128000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1788
_reflns_number_total             1878
_reflns_odcompleteness_completeness 98.98
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1878
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.088
_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)+(0.0404P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: S1(0.6) H1A(0.6) H1B(0.4) H4AA(0.6) H4AB(0.6) H4BC(0.4) H4BD(0.4)
 C7(0.6) H7A(0.6) H7B(0.6) C5(0.6) H5A(0.6) H5B(0.6) C6(0.6) H6(0.6) C1(0.6)
 H1(0.6) C3(0.6) H3(0.6) C2(0.6) H2A(0.6) H2B(0.6) S1B(0.4) C1B(0.4) H1BA(0.4)
 C6B(0.4) H6BA(0.4) H6BB(0.4) C3B(0.4) H3BA(0.4) H3BB(0.4) C7B(0.4) H7BA(0.4)
 H7BB(0.4) C5B(0.4) H5BA(0.4) C2B(0.4) H2BA(0.4)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C1(H1), C3(H3), C1B(H1BA), C5B(H5BA), C2B(H2BA)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4AA,H4AB), C4(H4BC,H4BD), C7(H7A,H7B), C5(H5A,H5B), C2(H2A,H2B), C6B(H6BA,
 H6BB), C3B(H3BA,H3BB), C7B(H7BA,H7BB)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N1(H1B)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.27556(13) 0.65838(16) 0.10065(15) 0.0378(3) Uani 0.6 1 d . . P A 1
N1 N 0.53321(13) 0.63772(13) 0.32555(12) 0.0358(3) Uani 1 1 d . . . . .
H1A H 0.611390 0.678820 0.391630 0.043 Uiso 0.6 1 calc R U P B 1
H1B H 0.579668 0.662205 0.416004 0.043 Uiso 0.4 1 calc R U P C 2
C8 C 0.42618(14) 0.72086(15) 0.23854(14) 0.0316(3) Uani 1 1 d . . . . .
C9 C 0.43439(16) 0.87619(16) 0.27829(15) 0.0362(4) Uani 1 1 d . . . . .
H9A H 0.441681 0.936122 0.206441 0.054 Uiso 1 1 calc R U . . .
H9B H 0.518564 0.891966 0.371129 0.054 Uiso 1 1 calc R U . . .
H9C H 0.348339 0.903177 0.283585 0.054 Uiso 1 1 calc R U . . .
C4 C 0.67011(19) 0.19900(17) 0.32488(19) 0.0420(4) Uani 1 1 d . . . . .
H4AA H 0.594208 0.144770 0.244296 0.050 Uiso 0.6 1 calc R U P D 1
H4AB H 0.757186 0.138286 0.370247 0.050 Uiso 0.6 1 calc R U P D 1
H4BC H 0.606359 0.173363 0.224048 0.050 Uiso 0.4 1 calc R U P E 2
H4BD H 0.720707 0.110690 0.377781 0.050 Uiso 0.4 1 calc R U P E 2
C7 C 0.7732(4) 0.4249(6) 0.4166(6) 0.0307(9) Uani 0.6 1 d . . P F 1
H7A H 0.793965 0.527932 0.407040 0.037 Uiso 0.6 1 calc R U P F 1
H7B H 0.861012 0.375184 0.487145 0.037 Uiso 0.6 1 calc R U P F 1
C5 C 0.6219(7) 0.2434(7) 0.4317(7) 0.0394(12) Uani 0.6 1 d . . P F 1
H5A H 0.678411 0.192726 0.523598 0.047 Uiso 0.6 1 calc R U P F 1
H5B H 0.519638 0.221057 0.395341 0.047 Uiso 0.6 1 calc R U P F 1
C6 C 0.6482(3) 0.4072(3) 0.4488(3) 0.0273(6) Uani 0.6 1 d . . P F 1
H6 H 0.664398 0.448514 0.541677 0.033 Uiso 0.6 1 calc R U P F 1
C1 C 0.5257(2) 0.4772(2) 0.3153(2) 0.0229(4) Uani 0.6 1 d . . P F 1
H1 H 0.430411 0.439993 0.296870 0.028 Uiso 0.6 1 calc R U P F 1
C3 C 0.7005(3) 0.3464(3) 0.2750(3) 0.0344(6) Uani 0.6 1 d . . P F 1
H3 H 0.758234 0.339671 0.224327 0.041 Uiso 0.6 1 calc R U P F 1
C2 C 0.5600(2) 0.4334(3) 0.1951(2) 0.0305(5) Uani 0.6 1 d . . P F 1
H2A H 0.483123 0.372476 0.122619 0.037 Uiso 0.6 1 calc R U P F 1
H2B H 0.573401 0.520192 0.148217 0.037 Uiso 0.6 1 calc R U P F 1
S1B S 0.3111(2) 0.6577(3) 0.0715(2) 0.0565(6) Uani 0.4 1 d . . P A 2
C1B C 0.5822(4) 0.4997(4) 0.2784(3) 0.0233(6) Uani 0.4 1 d . . P F 2
H1BA H 0.579220 0.511461 0.184202 0.028 Uiso 0.4 1 calc R U P F 2
C6B C 0.4842(4) 0.3758(4) 0.2787(4) 0.0320(7) Uani 0.4 1 d . . P F 2
H6BA H 0.412869 0.412944 0.304784 0.038 Uiso 0.4 1 calc R U P F 2
H6BB H 0.433756 0.328402 0.184264 0.038 Uiso 0.4 1 calc R U P F 2
C3B C 0.7785(5) 0.3229(4) 0.3388(5) 0.0316(8) Uani 0.4 1 d . . P F 2
H3BA H 0.877963 0.294294 0.405399 0.038 Uiso 0.4 1 calc R U P F 2
H3BB H 0.770666 0.346479 0.245181 0.038 Uiso 0.4 1 calc R U P F 2
C7B C 0.6934(5) 0.3744(5) 0.5021(5) 0.0312(10) Uani 0.4 1 d . . P F 2
H7BA H 0.776272 0.324082 0.579399 0.037 Uiso 0.4 1 calc R U P F 2
H7BB H 0.648237 0.439529 0.542510 0.037 Uiso 0.4 1 calc R U P F 2
C5B C 0.5878(9) 0.2701(10) 0.3915(9) 0.0340(15) Uani 0.4 1 d . . P F 2
H5BA H 0.541950 0.200336 0.428890 0.041 Uiso 0.4 1 calc R U P F 2
C2B C 0.7308(6) 0.4523(8) 0.3978(8) 0.0237(12) Uani 0.4 1 d . . P F 2
H2BA H 0.802203 0.532465 0.440142 0.028 Uiso 0.4 1 calc R U P F 2


_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 1.6794(19) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C8 1.3188(18) . ?
N1 C1 1.481(2) . ?
N1 C1B 1.549(4) . ?
C8 C9 1.482(2) . ?
C8 S1B 1.714(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C4 H4AA 0.9900 . ?
C4 H4AB 0.9900 . ?
C4 H4BC 0.9900 . ?
C4 H4BD 0.9900 . ?
C4 C5 1.519(8) . ?
C4 C3 1.549(3) . ?
C4 C3B 1.580(4) . ?
C4 C5B 1.522(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.540(6) . ?
C7 C3 1.515(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.528(8) . ?
C6 H6 1.0000 . ?
C6 C1 1.542(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.552(3) . ?
C3 H3 1.0000 . ?
C3 C2 1.547(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1B H1BA 1.0000 . ?
C1B C6B 1.549(5) . ?
C1B C2B 1.548(6) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B C5B 1.533(7) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C2B 1.546(7) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C5B 1.522(11) . ?
C7B C2B 1.533(9) . ?
C5B H5BA 1.0000 . ?
C2B H2BA 1.0000 . ?

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 N1 H1A 119.0 . . ?
C8 N1 H1B 118.0 . . ?
C8 N1 C1 121.93(13) . . ?
C8 N1 C1B 124.05(15) . . ?
C1 N1 H1A 119.0 . . ?
C1B N1 H1B 118.0 . . ?
N1 C8 S1 124.24(12) . . ?
N1 C8 C9 116.43(12) . . ?
N1 C8 S1B 119.01(14) . . ?
C9 C8 S1 118.85(11) . . ?
C9 C8 S1B 122.74(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H4AA C4 H4AB 109.1 . . ?
H4BC C4 H4BD 109.2 . . ?
C5 C4 H4AA 111.1 . . ?
C5 C4 H4AB 111.1 . . ?
C5 C4 C3 103.1(3) . . ?
C3 C4 H4AA 111.1 . . ?
C3 C4 H4AB 111.1 . . ?
C3B C4 H4BC 111.4 . . ?
C3B C4 H4BD 111.4 . . ?
C5B C4 H4BC 111.4 . . ?
C5B C4 H4BD 111.4 . . ?
C5B C4 C3B 102.0(4) . . ?
H7A C7 H7B 110.2 . . ?
C6 C7 H7A 112.7 . . ?
C6 C7 H7B 112.7 . . ?
C3 C7 H7A 112.7 . . ?
C3 C7 H7B 112.7 . . ?
C3 C7 C6 95.2(3) . . ?
C4 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
C4 C5 C6 104.2(4) . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C7 C6 H6 115.3 . . ?
C7 C6 C1 100.9(3) . . ?
C5 C6 C7 102.0(4) . . ?
C5 C6 H6 115.3 . . ?
C5 C6 C1 106.0(3) . . ?
C1 C6 H6 115.3 . . ?
N1 C1 C6 110.91(18) . . ?
N1 C1 H1 111.8 . . ?
N1 C1 C2 107.15(19) . . ?
C6 C1 H1 111.8 . . ?
C6 C1 C2 103.11(19) . . ?
C2 C1 H1 111.8 . . ?
C4 C3 H3 114.8 . . ?
C7 C3 C4 99.4(3) . . ?
C7 C3 H3 114.8 . . ?
C7 C3 C2 101.6(2) . . ?
C2 C3 C4 109.6(2) . . ?
C2 C3 H3 114.8 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 C1 103.23(17) . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
N1 C1B H1BA 112.8 . . ?
N1 C1B C6B 105.6(3) . . ?
C6B C1B H1BA 112.8 . . ?
C2B C1B N1 109.5(3) . . ?
C2B C1B H1BA 112.8 . . ?
C2B C1B C6B 102.6(4) . . ?
C1B C6B H6BA 111.0 . . ?
C1B C6B H6BB 111.0 . . ?
H6BA C6B H6BB 109.0 . . ?
C5B C6B C1B 103.6(4) . . ?
C5B C6B H6BA 111.0 . . ?
C5B C6B H6BB 111.0 . . ?
C4 C3B H3BA 111.2 . . ?
C4 C3B H3BB 111.2 . . ?
H3BA C3B H3BB 109.1 . . ?
C2B C3B C4 103.0(4) . . ?
C2B C3B H3BA 111.2 . . ?
C2B C3B H3BB 111.2 . . ?
H7BA C7B H7BB 110.2 . . ?
C5B C7B H7BA 112.8 . . ?
C5B C7B H7BB 112.8 . . ?
C5B C7B C2B 94.8(5) . . ?
C2B C7B H7BA 112.8 . . ?
C2B C7B H7BB 112.8 . . ?
C4 C5B C6B 105.3(5) . . ?
C4 C5B C7B 104.9(6) . . ?
C4 C5B H5BA 114.6 . . ?
C6B C5B H5BA 114.6 . . ?
C7B C5B C6B 101.4(6) . . ?
C7B C5B H5BA 114.6 . . ?
C1B C2B H2BA 115.1 . . ?
C3B C2B C1B 106.7(5) . . ?
C3B C2B H2BA 115.1 . . ?
C7B C2B C1B 102.2(4) . . ?
C7B C2B C3B 100.9(5) . . ?
C7B C2B H2BA 115.1 . . ?

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
N1 C1 C2 C3 115.76(18) . . . . ?
N1 C1B C6B C5B -117.3(5) . . . . ?
N1 C1B C2B C3B -175.2(4) . . . . ?
N1 C1B C2B C7B 79.3(5) . . . . ?
C8 N1 C1 C6 -166.76(18) . . . . ?
C8 N1 C1 C2 81.4(2) . . . . ?
C8 N1 C1B C6B -84.3(3) . . . . ?
C8 N1 C1B C2B 166.0(4) . . . . ?
C4 C5 C6 C7 -28.3(4) . . . . ?
C4 C5 C6 C1 77.0(4) . . . . ?
C4 C3 C2 C1 70.4(2) . . . . ?
C4 C3B C2B C1B -67.7(5) . . . . ?
C4 C3B C2B C7B 38.7(4) . . . . ?
C7 C6 C1 N1 -78.7(3) . . . . ?
C7 C6 C1 C2 35.7(3) . . . . ?
C7 C3 C2 C1 -34.2(3) . . . . ?
C5 C4 C3 C7 41.1(3) . . . . ?
C5 C4 C3 C2 -64.9(3) . . . . ?
C5 C6 C1 N1 175.3(3) . . . . ?
C5 C6 C1 C2 -70.3(4) . . . . ?
C6 C7 C3 C4 -57.1(3) . . . . ?
C6 C7 C3 C2 55.3(3) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C1 N1 C8 S1 -4.5(2) . . . . ?
C1 N1 C8 C9 167.44(17) . . . . ?
C3 C4 C5 C6 -7.5(4) . . . . ?
C3 C7 C6 C5 53.1(4) . . . . ?
C3 C7 C6 C1 -56.1(3) . . . . ?
C1B N1 C8 C9 -151.7(2) . . . . ?
C1B N1 C8 S1B 13.3(3) . . . . ?
C1B C6B C5B C4 -71.9(6) . . . . ?
C1B C6B C5B C7B 37.1(6) . . . . ?
C6B C1B C2B C3B 73.0(5) . . . . ?
C6B C1B C2B C7B -32.5(5) . . . . ?
C3B C4 C5B C6B 76.5(5) . . . . ?
C3B C4 C5B C7B -30.1(5) . . . . ?
C5B C4 C3B C2B -5.6(5) . . . . ?
C5B C7B C2B C1B 54.4(5) . . . . ?
C5B C7B C2B C3B -55.5(5) . . . . ?
C2B C1B C6B C5B -2.6(6) . . . . ?
C2B C7B C5B C4 53.5(5) . . . . ?
C2B C7B C5B C6B -56.0(6) . . . . ?

_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 2.380
_oxdiff_exptl_absorpt_empirical_full_min 0.381
####################################################################### 
# 
# 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_tangshizhong2_0425_auto
_database_code_depnum_ccdc_archive 'CCDC 2168880'
loop_
_audit_author_name
_audit_author_address
'Shi-Zhong Tang'
;The University of LanZhou
China
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H21 N S'
_chemical_formula_sum            'C13 H21 N S'
_chemical_formula_weight         223.37
_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'
N N 0.0311 0.0180 '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                   11.16255(17)
_cell_length_b                   10.98512(17)
_cell_length_c                   10.23216(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.9987(13)
_cell_angle_gamma                90
_cell_volume                     1249.92(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7016
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.3990
_cell_measurement_theta_min      3.9590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.566
_diffrn_reflns_theta_min         3.975
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00 105.00   0.50    0.05    --   47.57 147.00 -11.00   88
  2  ω     90.00 115.00   0.50    0.08    --  107.75 147.00 -11.00   50
  3  ω     79.00 142.00   0.50    0.08    --  107.75 124.00-177.00  126
  4  ω    131.00 174.00   0.50    0.08    --  107.75  19.00   0.00   86
  5  ω     95.00 121.00   0.50    0.08    --  107.75  19.00   0.00   52
  6  ω     46.00  72.00   0.50    0.08    --  107.75 -99.00 120.00   52
  7  ω     74.00 108.00   0.50    0.08    --  107.75-124.00 103.00   68
  8  ω     35.00  62.00   0.50    0.08    --  107.75 -57.00  60.00   54
  9  ω     67.00 120.00   0.50    0.08    --  107.75-147.00 -61.00  106
 10  ω     67.00 103.00   0.50    0.08    --  107.75 -77.00 -60.00   72
 11  ω     38.00  63.00   0.50    0.08    --  107.75 -57.00-120.00   50
 12  ω     46.00  72.00   0.50    0.08    --  107.75 -77.00-180.00   52
 13  ω    -23.00  23.00   0.50    0.05    --   47.57 -19.00-150.00   92
 14  ω    -26.00  22.00   0.50    0.05    --   47.57 -19.00  90.00   96
 15  ω    -26.00  26.00   0.50    0.05    --  -47.57  19.00 -60.00  104
 16  ω    -93.00 -44.00   0.50    0.05    --  -47.57 124.00-177.00   98
 17  ω    -97.00 -70.00   0.50    0.05    --  -47.57 147.00 -11.00   54
 18  ω   -105.00 -79.00   0.50    0.08    -- -100.00 147.00 -11.00   52
 19  ω   -122.00 -65.00   0.50    0.08    -- -100.00 140.00  85.57  114
 20  ω   -112.00 -46.00   0.50    0.08    -- -100.00 125.00 120.00  132
 21  ω    -64.00 -27.00   0.50    0.08    -- -100.00  57.00 -30.00   74
 22  ω   -172.00 -85.00   0.50    0.08    -- -100.00 -57.00 150.00  174
 23  ω   -115.00 -80.00   0.50    0.08    -- -100.00 -77.00 120.00   70
 24  ω   -172.00-126.00   0.50    0.08    -- -100.00 -77.00 120.00   92
 25  ω   -118.00 -89.00   0.50    0.05    --  -47.57-147.00 -61.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0835033000
_diffrn_orient_matrix_UB_12      0.1118992000
_diffrn_orient_matrix_UB_13      -0.0089097000
_diffrn_orient_matrix_UB_21      -0.1097285000
_diffrn_orient_matrix_UB_22      -0.0837289000
_diffrn_orient_matrix_UB_23      0.0085979000
_diffrn_orient_matrix_UB_31      0.0134444000
_diffrn_orient_matrix_UB_32      0.0114650000
_diffrn_orient_matrix_UB_33      0.1506373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2346
_reflns_number_total             2508
_reflns_odcompleteness_completeness 99.92
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.076
_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)+(0.0752P)²+0.9405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C5(H5), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_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 0.53442(4) 0.37625(4) 0.35741(4) 0.02443(18) Uani 1 1 d . . . . .
N1 N 0.58374(13) 0.30337(14) 0.60218(14) 0.0207(3) Uani 1 1 d . . . . .
H1 H 0.565834 0.259899 0.670048 0.025 Uiso 1 1 calc R U . . .
C1 C 0.69026(16) 0.38065(16) 0.61766(17) 0.0203(4) Uani 1 1 d . . . . .
H1A H 0.677368 0.455151 0.562050 0.024 Uiso 1 1 calc R U . . .
C2 C 0.72409(17) 0.4177(2) 0.76193(18) 0.0278(4) Uani 1 1 d . . . . .
H2A H 0.712781 0.506149 0.774579 0.033 Uiso 1 1 calc R U . . .
H2B H 0.675197 0.372591 0.822058 0.033 Uiso 1 1 calc R U . . .
C3 C 0.92954(18) 0.4632(2) 0.6963(2) 0.0342(5) Uani 1 1 d . . . . .
H3A H 1.016852 0.456380 0.722012 0.041 Uiso 1 1 calc R U . . .
H3B H 0.905289 0.549702 0.700240 0.041 Uiso 1 1 calc R U . . .
C4 C 0.8965(2) 0.4086(2) 0.5564(2) 0.0395(5) Uani 1 1 d . . . . .
H4A H 0.862746 0.471696 0.494756 0.047 Uiso 1 1 calc R U . . .
H4B H 0.967780 0.371586 0.520895 0.047 Uiso 1 1 calc R U . . .
C5 C 0.80271(18) 0.3123(2) 0.5806(2) 0.0319(5) Uani 1 1 d . . . . .
H5 H 0.787876 0.250621 0.509160 0.038 Uiso 1 1 calc R U . . .
C6 C 0.85376(18) 0.2604(2) 0.7153(2) 0.0335(5) Uani 1 1 d . . . . .
H6A H 0.798835 0.201335 0.752311 0.040 Uiso 1 1 calc R U . . .
H6B H 0.934834 0.224402 0.712748 0.040 Uiso 1 1 calc R U . . .
C7 C 0.85597(18) 0.3829(2) 0.7844(2) 0.0311(5) Uani 1 1 d . . . . .
H7 H 0.888085 0.380432 0.878694 0.037 Uiso 1 1 calc R U . . .
C8 C 0.51242(16) 0.29462(16) 0.49241(17) 0.0202(4) Uani 1 1 d . . . . .
C9 C 0.40773(17) 0.20774(18) 0.49793(18) 0.0253(4) Uani 1 1 d . . . . .
H9 H 0.417247 0.163498 0.583616 0.030 Uiso 1 1 calc R U . . .
C10 C 0.28451(19) 0.2713(2) 0.4861(3) 0.0397(5) Uani 1 1 d . . . . .
H10A H 0.267286 0.307596 0.570991 0.048 Uiso 1 1 calc R U . . .
H10B H 0.281874 0.336283 0.418858 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1947(2) 0.1714(3) 0.4459(3) 0.0566(8) Uani 1 1 d . . . . .
H11A H 0.131988 0.202092 0.379763 0.068 Uiso 1 1 calc R U . . .
H11B H 0.155353 0.141885 0.523000 0.068 Uiso 1 1 calc R U . . .
C12 C 0.2668(2) 0.0681(2) 0.3879(2) 0.0429(6) Uani 1 1 d . . . . .
H12A H 0.264128 -0.006284 0.442183 0.052 Uiso 1 1 calc R U . . .
H12B H 0.233038 0.048755 0.297557 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3947(2) 0.1135(2) 0.3872(2) 0.0335(5) Uani 1 1 d . . . . .
H13A H 0.407973 0.151319 0.301841 0.040 Uiso 1 1 calc R U . . .
H13B H 0.452774 0.046020 0.404294 0.040 Uiso 1 1 calc R U . . .


_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 1.6828(18) . ?
N1 H1 0.8800 . ?
N1 C1 1.458(2) . ?
N1 C8 1.322(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.546(2) . ?
C1 C5 1.538(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C7 1.519(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.565(3) . ?
C3 C7 1.547(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.523(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.554(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.520(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.514(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.538(3) . ?
C9 C13 1.533(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.540(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.513(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C1 N1 H1 118.0 . . ?
C8 N1 H1 118.0 . . ?
C8 N1 C1 124.01(15) . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 C2 112.70(14) . . ?
N1 C1 C5 111.37(15) . . ?
C2 C1 H1A 109.8 . . ?
C5 C1 H1A 109.8 . . ?
C5 C1 C2 103.13(15) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C7 C2 C1 103.37(16) . . ?
C7 C2 H2A 111.1 . . ?
C7 C2 H2B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C7 C3 H3A 111.2 . . ?
C7 C3 H3B 111.2 . . ?
C7 C3 C4 102.69(17) . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 103.18(17) . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C1 C5 H5 115.1 . . ?
C1 C5 C6 101.80(16) . . ?
C4 C5 C1 106.78(18) . . ?
C4 C5 H5 115.1 . . ?
C4 C5 C6 101.23(17) . . ?
C6 C5 H5 115.1 . . ?
C5 C6 H6A 112.8 . . ?
C5 C6 H6B 112.8 . . ?
H6A C6 H6B 110.3 . . ?
C7 C6 C5 94.42(16) . . ?
C7 C6 H6A 112.8 . . ?
C7 C6 H6B 112.8 . . ?
C2 C7 C3 108.99(17) . . ?
C2 C7 C6 100.13(16) . . ?
C2 C7 H7 114.5 . . ?
C3 C7 H7 114.5 . . ?
C6 C7 C3 102.81(18) . . ?
C6 C7 H7 114.5 . . ?
N1 C8 S1 122.57(14) . . ?
N1 C8 C9 115.07(15) . . ?
C9 C8 S1 122.34(13) . . ?
C8 C9 H9 108.4 . . ?
C8 C9 C10 113.51(17) . . ?
C8 C9 C13 114.99(17) . . ?
C10 C9 H9 108.4 . . ?
C13 C9 H9 108.4 . . ?
C13 C9 C10 102.81(16) . . ?
C9 C10 H10A 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C9 104.95(19) . . ?
C11 C10 H10A 110.8 . . ?
C11 C10 H10B 110.8 . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
C10 C11 C12 106.4(2) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 C11 106.50(19) . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C9 C13 H13A 110.9 . . ?
C9 C13 H13B 110.9 . . ?
C12 C13 C9 104.37(18) . . ?
C12 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?

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 C8 C9 C10 -65.1(2) . . . . ?
S1 C8 C9 C13 52.9(2) . . . . ?
N1 C1 C2 C7 127.90(17) . . . . ?
N1 C1 C5 C4 161.74(16) . . . . ?
N1 C1 C5 C6 -92.55(18) . . . . ?
N1 C8 C9 C10 113.64(19) . . . . ?
N1 C8 C9 C13 -128.35(18) . . . . ?
C1 N1 C8 S1 -2.0(3) . . . . ?
C1 N1 C8 C9 179.32(16) . . . . ?
C1 C2 C7 C3 65.3(2) . . . . ?
C1 C2 C7 C6 -42.11(19) . . . . ?
C1 C5 C6 C7 -53.38(18) . . . . ?
C2 C1 C5 C4 -77.15(19) . . . . ?
C2 C1 C5 C6 28.56(19) . . . . ?
C3 C4 C5 C1 68.2(2) . . . . ?
C3 C4 C5 C6 -37.9(2) . . . . ?
C4 C3 C7 C2 -73.5(2) . . . . ?
C4 C3 C7 C6 32.1(2) . . . . ?
C4 C5 C6 C7 56.63(19) . . . . ?
C5 C1 C2 C7 7.69(19) . . . . ?
C5 C6 C7 C2 58.30(17) . . . . ?
C5 C6 C7 C3 -54.01(17) . . . . ?
C7 C3 C4 C5 4.1(2) . . . . ?
C8 N1 C1 C2 155.02(17) . . . . ?
C8 N1 C1 C5 -89.6(2) . . . . ?
C8 C9 C10 C11 160.7(2) . . . . ?
C8 C9 C13 C12 -162.00(18) . . . . ?
C9 C10 C11 C12 -20.1(3) . . . . ?
C10 C9 C13 C12 -38.1(2) . . . . ?
C10 C11 C12 C13 -3.7(3) . . . . ?
C11 C12 C13 C9 26.0(3) . . . . ?
C13 C9 C10 C11 35.9(3) . . . . ?

_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 2.678
_oxdiff_exptl_absorpt_empirical_full_min 0.473
####################################################################### 
# 
# 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_tangshizhong3_0425_auto
_database_code_depnum_ccdc_archive 'CCDC 2168881'
loop_
_audit_author_name
_audit_author_address
'Shi-Zhong Tang'
;The University of LanZhou
China
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H23 N S'
_chemical_formula_sum            'C14 H23 N S'
_chemical_formula_weight         237.39
_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'
N N 0.0311 0.0180 '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                   11.57483(18)
_cell_length_b                   11.2206(2)
_cell_length_c                   10.30302(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.9195(14)
_cell_angle_gamma                90
_cell_volume                     1334.99(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.7890
_cell_measurement_theta_min      3.8380
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.615
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.988
_diffrn_reflns_theta_min         3.828
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     62.00 117.00   0.50    0.05    --   47.57 148.00-143.00  110
  2  ω     61.00  87.00   0.50    0.10    --  107.75 148.00-143.00   52
  3  ω    102.00 127.00   0.50    0.10    --  107.75 123.00  51.00   50
  4  ω     88.00 124.00   0.50    0.10    --  107.75 125.00  90.00   72
  5  ω    135.00 174.00   0.50    0.10    --  107.75 125.00  90.00   78
  6  ω     48.00  73.00   0.50    0.10    --  107.75-123.00 -28.00   50
  7  ω     37.00  64.00   0.50    0.10    --  107.75-148.00 167.00   54
  8  ω     86.00 128.00   0.50    0.10    --  107.75-148.00 167.00   84
  9  ω     44.00  69.00   0.50    0.05    --   47.57-148.00 167.00   50
 10  ω    -24.00  18.00   0.50    0.05    --   47.57 -19.00   0.00   84
 11  ω    -17.00  23.00   0.50    0.05    --   47.57 -19.00  30.00   80
 12  ω    -26.00  23.00   0.50    0.05    --   47.57 -19.00 -60.00   98
 13  ω    -18.00   8.00   0.50    0.05    --   47.57 -19.00-150.00   52
 14  ω     40.00  66.00   0.50    0.10    --  107.75 -77.00-180.00   52
 15  ω     77.00 102.00   0.50    0.10    --  107.75 -77.00-180.00   50
 16  ω     37.00  62.00   0.50    0.10    --  107.75 -57.00-150.00   50
 17  ω     38.00  63.00   0.50    0.10    --  107.75 -57.00 120.00   50
 18  ω   -100.00 -67.00   0.50    0.05    --  -47.57-148.00 167.00   66
 19  ω   -171.00 -86.00   0.50    0.10    -- -100.00 -57.00-120.00  170
 20  ω   -175.00-139.00   0.50    0.10    -- -100.00 -19.00 150.00   72
 21  ω   -118.00 -91.00   0.50    0.10    -- -100.00 -19.00 150.00   54
 22  ω    -68.00 -27.00   0.50    0.10    -- -100.00  57.00  90.00   82
 23  ω    -62.00 -37.00   0.50    0.10    -- -100.00  57.00  30.00   50
 24  ω   -112.00 -36.00   0.50    0.10    -- -100.00 125.00   0.00  152
 25  ω    -68.00 -43.00   0.50    0.10    -- -100.00 123.00  51.00   50
 26  ω    -94.00 -68.00   0.50    0.05    --  -47.57 123.00  51.00   52
 27  ω    -69.00 -44.00   0.50    0.10    -- -100.00  57.00-120.00   50
 28  ω   -109.00 -89.00   0.50    0.05    --  -47.57 148.00-143.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0277500000
_diffrn_orient_matrix_UB_12      -0.1338150000
_diffrn_orient_matrix_UB_13      0.0109624000
_diffrn_orient_matrix_UB_21      0.1304384000
_diffrn_orient_matrix_UB_22      -0.0284366000
_diffrn_orient_matrix_UB_23      0.0114890000
_diffrn_orient_matrix_UB_31      0.0009992000
_diffrn_orient_matrix_UB_32      0.0119878000
_diffrn_orient_matrix_UB_33      0.1490680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2391
_reflns_number_total             2659
_reflns_odcompleteness_completeness 98.77
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.090
_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)+(0.0723P)²+0.5879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_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 0.53482(4) 0.62548(4) 0.35067(4) 0.02518(17) Uani 1 1 d . . . . .
N1 N 0.58313(12) 0.69634(13) 0.59270(12) 0.0214(3) Uani 1 1 d . . . . .
H1 H 0.567134 0.740167 0.659994 0.026 Uiso 1 1 calc R U . . .
C1 C 0.40999(14) 0.78600(16) 0.49616(15) 0.0214(4) Uani 1 1 d . . . . .
H1A H 0.421109 0.830330 0.580285 0.026 Uiso 1 1 calc R U . . .
C2 C 0.3994(2) 0.8775(2) 0.3867(2) 0.0398(5) Uani 1 1 d . . . . .
H2A H 0.392789 0.835891 0.301836 0.048 Uiso 1 1 calc R U . . .
H2B H 0.469981 0.927522 0.389868 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2929(2) 0.9573(2) 0.3988(2) 0.0513(7) Uani 1 1 d . . . . .
H3A H 0.304673 1.007204 0.477799 0.062 Uiso 1 1 calc R U . . .
H3B H 0.284190 1.011089 0.322583 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1832(2) 0.8847(3) 0.4065(3) 0.0613(8) Uani 1 1 d . . . . .
H4A H 0.117963 0.938846 0.421678 0.074 Uiso 1 1 calc R U . . .
H4B H 0.165412 0.843586 0.322554 0.074 Uiso 1 1 calc R U . . .
C5 C 0.19482(17) 0.7933(2) 0.5147(3) 0.0496(6) Uani 1 1 d . . . . .
H5A H 0.123477 0.744484 0.513201 0.060 Uiso 1 1 calc R U . . .
H5B H 0.203682 0.834644 0.599661 0.060 Uiso 1 1 calc R U . . .
C6 C 0.29919(16) 0.7119(2) 0.5002(2) 0.0367(5) Uani 1 1 d . . . . .
H6A H 0.287267 0.664797 0.419091 0.044 Uiso 1 1 calc R U . . .
H6B H 0.306910 0.655614 0.574311 0.044 Uiso 1 1 calc R U . . .
C7 C 0.51342(14) 0.70416(15) 0.48605(15) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.68507(14) 0.61950(15) 0.60587(16) 0.0221(4) Uani 1 1 d . . . . .
H8 H 0.670383 0.545426 0.553344 0.027 Uiso 1 1 calc R U . . .
C9 C 0.79515(15) 0.68177(19) 0.56290(18) 0.0309(4) Uani 1 1 d . . . . .
H9 H 0.781949 0.740476 0.490376 0.037 Uiso 1 1 calc R U . . .
C10 C 0.88166(16) 0.5825(2) 0.5385(2) 0.0368(5) Uani 1 1 d . . . . .
H10A H 0.950531 0.614332 0.498314 0.044 Uiso 1 1 calc R U . . .
H10B H 0.845605 0.519826 0.481488 0.044 Uiso 1 1 calc R U . . .
C11 C 0.91428(16) 0.5335(2) 0.67676(19) 0.0347(5) Uani 1 1 d . . . . .
H11A H 0.889572 0.449483 0.684637 0.042 Uiso 1 1 calc R U . . .
H11B H 0.998792 0.538875 0.698308 0.042 Uiso 1 1 calc R U . . .
C12 C 0.84725(17) 0.61556(19) 0.76554(19) 0.0342(5) Uani 1 1 d . . . . .
H12 H 0.879773 0.619226 0.857901 0.041 Uiso 1 1 calc R U . . .
C13 C 0.71868(16) 0.5856(2) 0.74902(17) 0.0311(4) Uani 1 1 d . . . . .
H13A H 0.674012 0.632886 0.809427 0.037 Uiso 1 1 calc R U . . .
H13B H 0.705240 0.499775 0.764380 0.037 Uiso 1 1 calc R U . . .
C14 C 0.84770(17) 0.73443(19) 0.6928(2) 0.0364(5) Uani 1 1 d . . . . .
H14A H 0.926634 0.766768 0.685960 0.044 Uiso 1 1 calc R U . . .
H14B H 0.797270 0.795074 0.729840 0.044 Uiso 1 1 calc R U . . .


_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 C7 1.6832(16) . ?
N1 H1 0.8800 . ?
N1 C7 1.321(2) . ?
N1 C8 1.460(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.524(2) . ?
C1 C6 1.532(2) . ?
C1 C7 1.518(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.535(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.514(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.514(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8 1.0000 . ?
C8 C9 1.544(2) . ?
C8 C13 1.547(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.530(3) . ?
C9 C14 1.549(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.549(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.544(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.524(3) . ?
C12 C14 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
C7 N1 H1 118.0 . . ?
C7 N1 C8 124.08(14) . . ?
C8 N1 H1 118.0 . . ?
C2 C1 H1A 107.8 . . ?
C2 C1 C6 111.14(16) . . ?
C6 C1 H1A 107.8 . . ?
C7 C1 H1A 107.8 . . ?
C7 C1 C2 112.41(14) . . ?
C7 C1 C6 109.82(15) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 110.96(16) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.8(2) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 111.77(18) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.3(2) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 C1 110.27(18) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 S1 122.57(13) . . ?
N1 C7 C1 115.01(13) . . ?
C1 C7 S1 122.38(11) . . ?
N1 C8 H8 109.5 . . ?
N1 C8 C9 112.55(15) . . ?
N1 C8 C13 112.50(13) . . ?
C9 C8 H8 109.5 . . ?
C9 C8 C13 103.06(14) . . ?
C13 C8 H8 109.5 . . ?
C8 C9 H9 115.2 . . ?
C8 C9 C14 102.00(14) . . ?
C10 C9 C8 106.23(17) . . ?
C10 C9 H9 115.2 . . ?
C10 C9 C14 101.35(15) . . ?
C14 C9 H9 115.2 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C9 C10 C11 103.21(15) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 C10 103.43(16) . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C11 C12 H12 114.6 . . ?
C13 C12 C11 109.20(16) . . ?
C13 C12 H12 114.6 . . ?
C13 C12 C14 99.99(15) . . ?
C14 C12 C11 102.18(17) . . ?
C14 C12 H12 114.6 . . ?
C8 C13 H13A 111.1 . . ?
C8 C13 H13B 111.1 . . ?
C12 C13 C8 103.43(15) . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
C9 C14 H14A 112.9 . . ?
C9 C14 H14B 112.9 . . ?
C12 C14 C9 94.38(16) . . ?
C12 C14 H14A 112.9 . . ?
C12 C14 H14B 112.9 . . ?
H14A C14 H14B 110.3 . . ?

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
N1 C8 C9 C10 -161.55(14) . . . . ?
N1 C8 C9 C14 92.69(17) . . . . ?
N1 C8 C13 C12 -129.21(16) . . . . ?
C1 C2 C3 C4 -54.1(3) . . . . ?
C2 C1 C6 C5 -56.8(2) . . . . ?
C2 C1 C7 S1 -54.4(2) . . . . ?
C2 C1 C7 N1 127.74(17) . . . . ?
C2 C3 C4 C5 54.2(3) . . . . ?
C3 C4 C5 C6 -55.6(3) . . . . ?
C4 C5 C6 C1 56.5(2) . . . . ?
C6 C1 C2 C3 55.5(2) . . . . ?
C6 C1 C7 S1 69.90(17) . . . . ?
C6 C1 C7 N1 -107.97(17) . . . . ?
C7 N1 C8 C9 88.9(2) . . . . ?
C7 N1 C8 C13 -155.17(16) . . . . ?
C7 C1 C2 C3 179.06(18) . . . . ?
C7 C1 C6 C5 178.22(16) . . . . ?
C8 N1 C7 S1 -0.2(2) . . . . ?
C8 N1 C7 C1 177.62(15) . . . . ?
C8 C9 C10 C11 -69.07(19) . . . . ?
C8 C9 C14 C12 53.42(17) . . . . ?
C9 C8 C13 C12 -7.73(19) . . . . ?
C9 C10 C11 C12 -3.0(2) . . . . ?
C10 C9 C14 C12 -56.10(17) . . . . ?
C10 C11 C12 C13 72.5(2) . . . . ?
C10 C11 C12 C14 -32.72(19) . . . . ?
C11 C12 C13 C8 -64.8(2) . . . . ?
C11 C12 C14 C9 54.07(16) . . . . ?
C13 C8 C9 C10 77.00(17) . . . . ?
C13 C8 C9 C14 -28.75(18) . . . . ?
C13 C12 C14 C9 -58.24(16) . . . . ?
C14 C9 C10 C11 37.16(19) . . . . ?
C14 C12 C13 C8 41.93(18) . . . . ?

_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 2.745
_oxdiff_exptl_absorpt_empirical_full_min 0.403
