# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_g210605a
_database_code_depnum_ccdc_archive 'CCDC 2102830'
loop_
_audit_author_name
_audit_author_address
JS-g
;Soochow University
China
;
_audit_update_record             
;
2021-08-12 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-06-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 S'
_chemical_formula_sum            'C21 H16 N2 S'
_chemical_formula_weight         328.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N S'
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                   9.3674(7)
_cell_length_b                   23.7692(18)
_cell_length_c                   8.4101(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.905(9)
_cell_angle_gamma                90
_cell_volume                     1698.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1699
_cell_measurement_temperature    290.45(10)
_cell_measurement_theta_max      75.6740
_cell_measurement_theta_min      3.6930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.455
_diffrn_reflns_theta_min         3.719
_diffrn_ambient_temperature      290.45(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093   37.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093  -57.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00  -29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093  125.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.1093   37.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega   49.00   82.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   78.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00  102.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega  101.00  142.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   61.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  146.00  173.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   69.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   58.00   99.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega  103.00  155.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega   78.00  103.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00  115.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega  125.00  168.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
 17 omega  104.00  146.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  111.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   71.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   30.00   66.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 20 omega   71.00  105.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 21 omega   91.00  116.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -111.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  133.00  173.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   88.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 24 omega   71.00   96.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   46.00   71.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   41.00  116.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000   60.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1496468000
_diffrn_orient_matrix_UB_12      -0.0338480000
_diffrn_orient_matrix_UB_13      -0.1088733000
_diffrn_orient_matrix_UB_21      -0.1004567000
_diffrn_orient_matrix_UB_22      0.0533327000
_diffrn_orient_matrix_UB_23      -0.0229042000
_diffrn_orient_matrix_UB_31      0.0189239000
_diffrn_orient_matrix_UB_32      0.0146771000
_diffrn_orient_matrix_UB_33      -0.1685203000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2474
_reflns_number_total             3598
_reflns_odcompleteness_completeness 96.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.417
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.542
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     529
_refine_ls_R_factor_all          0.1780
_refine_ls_R_factor_gt           0.1459
_refine_ls_restrained_S_all      1.505
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3927
_refine_ls_wR_factor_ref         0.4383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 S1, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim C12 \\sim C11 \\sim C13 \\sim C9 \\sim C4 \\sim C1 \\sim C3 \\sim C17
\\sim C14 \\sim C6 \\sim C15 \\sim C7 \\sim C19 \\sim C8 \\sim C18 \\sim C20
\\sim C5 \\sim C16 \\sim C21 \\sim C10: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 3.8A
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C4(H4), C1(H1), C3(H3), C17(H17), C14(H14), C15(H15),
 C18(H18), C20(H20), C16(H16), C21(H21)
;
_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 -0.0095(3) 0.58826(11) 0.1111(2) 0.0799(8) Uani 1 1 d . U . . .
N1 N 0.0973(5) 0.6757(2) 0.6711(7) 0.0488(11) Uani 1 1 d . . . . .
C2 C 0.2921(7) 0.6981(2) 1.1862(8) 0.0513(11) Uani 1 1 d . U . . .
H2 H 0.290693 0.721515 1.274039 0.062 Uiso 1 1 calc R U . . .
N2 N 0.4176(7) 0.5182(2) 0.7423(8) 0.0594(13) Uani 1 1 d . . . . .
C12 C 0.5072(6) 0.6094(2) 0.6950(6) 0.0436(10) Uani 1 1 d . U . . .
C11 C 0.3938(6) 0.5708(2) 0.7178(6) 0.0440(9) Uani 1 1 d . U . . .
C13 C 0.4906(6) 0.6671(3) 0.6925(7) 0.0505(11) Uani 1 1 d . U . . .
H13 H 0.404690 0.682940 0.704170 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1624(6) 0.5346(3) 0.7331(7) 0.0493(11) Uani 1 1 d . U . . .
H9A H 0.122707 0.533676 0.822585 0.059 Uiso 1 1 calc R U . . .
H9B H 0.075518 0.528509 0.619552 0.059 Uiso 1 1 calc R U . . .
C4 C 0.3794(7) 0.6127(3) 1.0800(7) 0.0534(11) Uani 1 1 d . U . . .
H4 H 0.440549 0.580252 1.105325 0.064 Uiso 1 1 calc R U . . .
C1 C 0.1927(7) 0.7067(3) 0.9950(7) 0.0525(11) Uani 1 1 d . U . . .
H1 H 0.128402 0.738366 0.961915 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3928(8) 0.6477(3) 1.2184(7) 0.0589(13) Uani 1 1 d . U . . .
H3 H 0.465550 0.639264 1.331681 0.071 Uiso 1 1 calc R U . . .
C17 C 0.6364(6) 0.5865(3) 0.6753(7) 0.0514(11) Uani 1 1 d . U . . .
H17 H 0.649324 0.547652 0.675586 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6013(7) 0.7017(3) 0.6728(8) 0.0556(12) Uani 1 1 d . U . . .
H14 H 0.588695 0.740525 0.671411 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1896(7) 0.6710(3) 0.8644(7) 0.0511(11) Uani 1 1 d . U . . .
C15 C 0.7296(7) 0.6795(3) 0.6551(8) 0.0585(13) Uani 1 1 d . U . . .
H15 H 0.803850 0.703004 0.643230 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2443(7) 0.5910(3) 0.7369(8) 0.0520(11) Uani 1 1 d . U . . .
C19 C 0.0597(7) 0.6245(3) 0.4219(8) 0.0587(12) Uani 1 1 d . U . . .
C8 C 0.1337(6) 0.6329(3) 0.6097(7) 0.0503(11) Uani 1 1 d . U . . .
C18 C 0.1046(7) 0.5831(3) 0.3277(7) 0.0556(12) Uani 1 1 d . U . . .
H18 H 0.185394 0.557118 0.378872 0.067 Uiso 1 1 calc R U . . .
C20 C -0.0737(7) 0.6597(3) 0.3046(8) 0.0612(14) Uani 1 1 d . U . . .
H20 H -0.119903 0.689170 0.338636 0.073 Uiso 1 1 calc R U . . .
C5 C 0.2810(7) 0.6235(3) 0.9087(7) 0.0518(11) Uani 1 1 d . U . . .
C16 C 0.7464(7) 0.6225(3) 0.6552(8) 0.0584(12) Uani 1 1 d . U . . .
H16 H 0.832120 0.607269 0.641662 0.070 Uiso 1 1 calc R U . . .
C21 C -0.1174(9) 0.6404(3) 0.1336(8) 0.0647(15) Uani 1 1 d . U . . .
H21 H -0.201570 0.655844 0.038447 0.078 Uiso 1 1 calc R U . . .
C10 C 0.2904(9) 0.4903(3) 0.7692(9) 0.0643(14) Uani 1 1 d . U . . .
H10A H 0.327808 0.476490 0.888478 0.077 Uiso 1 1 calc R U . . .
H10B H 0.249928 0.458763 0.689397 0.077 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 C18 1.684(6) . ?
S1 C21 1.660(9) . ?
N1 C6 1.490(8) . ?
N1 C8 1.251(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.494(8) . ?
C2 C3 1.478(9) . ?
N2 C11 1.271(8) . ?
N2 C10 1.462(9) . ?
C12 C11 1.476(7) . ?
C12 C13 1.380(9) . ?
C12 C17 1.400(7) . ?
C11 C7 1.551(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C7 1.538(8) . ?
C9 C10 1.528(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.392(8) . ?
C4 C5 1.369(8) . ?
C1 H1 0.9300 . ?
C1 C6 1.379(8) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.404(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(9) . ?
C6 C5 1.370(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.363(11) . ?
C7 C8 1.508(8) . ?
C7 C5 1.546(8) . ?
C19 C8 1.446(8) . ?
C19 C18 1.433(10) . ?
C19 C20 1.483(9) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.396(9) . ?
C16 H16 0.9300 . ?
C21 H21 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C21 S1 C18 94.0(3) . . ?
C8 N1 C6 104.9(5) . . ?
C1 C2 H2 124.2 . . ?
C3 C2 H2 124.2 . . ?
C3 C2 C1 111.7(5) . . ?
C11 N2 C10 111.9(5) . . ?
C13 C12 C11 122.5(5) . . ?
C13 C12 C17 118.9(5) . . ?
C17 C12 C11 118.6(5) . . ?
N2 C11 C12 123.1(5) . . ?
N2 C11 C7 113.0(5) . . ?
C12 C11 C7 123.5(5) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
H9A C9 H9B 108.9 . . ?
C7 C9 H9A 110.8 . . ?
C7 C9 H9B 110.8 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C10 C9 C7 104.7(5) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C5 C4 C3 123.4(6) . . ?
C2 C1 H1 117.7 . . ?
C6 C1 C2 124.6(6) . . ?
C6 C1 H1 117.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(6) . . ?
C4 C3 H3 119.8 . . ?
C12 C17 H17 120.3 . . ?
C12 C17 C16 119.4(6) . . ?
C16 C17 H17 120.3 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 H14 119.5 . . ?
C1 C6 N1 129.2(6) . . ?
C5 C6 N1 111.5(5) . . ?
C5 C6 C1 119.3(6) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.1(6) . . ?
C16 C15 H15 120.4 . . ?
C9 C7 C11 101.1(5) . . ?
C9 C7 C5 111.6(5) . . ?
C8 C7 C11 120.8(5) . . ?
C8 C7 C9 111.9(5) . . ?
C8 C7 C5 98.5(5) . . ?
C5 C7 C11 113.4(5) . . ?
C8 C19 C20 122.1(7) . . ?
C18 C19 C8 125.6(6) . . ?
C18 C19 C20 112.4(5) . . ?
N1 C8 C7 118.0(5) . . ?
N1 C8 C19 118.3(6) . . ?
C19 C8 C7 123.6(6) . . ?
S1 C18 H18 124.8 . . ?
C19 C18 S1 110.4(5) . . ?
C19 C18 H18 124.8 . . ?
C19 C20 H20 126.3 . . ?
C21 C20 C19 107.5(7) . . ?
C21 C20 H20 126.3 . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 C7 132.5(6) . . ?
C6 C5 C7 106.9(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 C17 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
S1 C21 H21 122.1 . . ?
C20 C21 S1 115.7(5) . . ?
C20 C21 H21 122.1 . . ?
N2 C10 C9 106.2(5) . . ?
N2 C10 H10A 110.5 . . ?
N2 C10 H10B 110.5 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?

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 C6 C5 C4 177.5(5) . . . . ?
N1 C6 C5 C7 -3.1(6) . . . . ?
C2 C1 C6 N1 -179.3(5) . . . . ?
C2 C1 C6 C5 1.0(9) . . . . ?
N2 C11 C7 C9 -13.7(6) . . . . ?
N2 C11 C7 C8 -137.7(6) . . . . ?
N2 C11 C7 C5 105.8(6) . . . . ?
C12 C11 C7 C9 173.3(4) . . . . ?
C12 C11 C7 C8 49.3(7) . . . . ?
C12 C11 C7 C5 -67.1(7) . . . . ?
C12 C13 C14 C15 0.1(9) . . . . ?
C12 C17 C16 C15 0.2(8) . . . . ?
C11 N2 C10 C9 7.4(7) . . . . ?
C11 C12 C13 C14 179.3(5) . . . . ?
C11 C12 C17 C16 -179.4(5) . . . . ?
C11 C7 C8 N1 -128.2(6) . . . . ?
C11 C7 C8 C19 56.0(8) . . . . ?
C11 C7 C5 C4 -47.7(9) . . . . ?
C11 C7 C5 C6 133.0(5) . . . . ?
C13 C12 C11 N2 -170.9(6) . . . . ?
C13 C12 C11 C7 1.4(7) . . . . ?
C13 C12 C17 C16 0.6(8) . . . . ?
C13 C14 C15 C16 0.7(9) . . . . ?
C9 C7 C8 N1 113.1(6) . . . . ?
C9 C7 C8 C19 -62.7(7) . . . . ?
C9 C7 C5 C4 65.7(8) . . . . ?
C9 C7 C5 C6 -113.6(5) . . . . ?
C1 C2 C3 C4 -4.5(8) . . . . ?
C1 C6 C5 C4 -2.8(9) . . . . ?
C1 C6 C5 C7 176.6(5) . . . . ?
C3 C2 C1 C6 2.5(8) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
C3 C4 C5 C7 -178.6(6) . . . . ?
C17 C12 C11 N2 9.1(8) . . . . ?
C17 C12 C11 C7 -178.7(5) . . . . ?
C17 C12 C13 C14 -0.7(8) . . . . ?
C14 C15 C16 C17 -0.9(9) . . . . ?
C6 N1 C8 C7 2.7(7) . . . . ?
C6 N1 C8 C19 178.7(5) . . . . ?
C7 C9 C10 N2 -15.5(6) . . . . ?
C19 C20 C21 S1 -2.1(8) . . . . ?
C8 N1 C6 C1 -179.2(6) . . . . ?
C8 N1 C6 C5 0.5(6) . . . . ?
C8 C7 C5 C4 -176.6(6) . . . . ?
C8 C7 C5 C6 4.1(6) . . . . ?
C8 C19 C18 S1 -179.0(5) . . . . ?
C8 C19 C20 C21 -179.6(6) . . . . ?
C18 S1 C21 C20 2.1(6) . . . . ?
C18 C19 C8 N1 169.7(6) . . . . ?
C18 C19 C8 C7 -14.5(9) . . . . ?
C18 C19 C20 C21 1.0(8) . . . . ?
C20 C19 C8 N1 -9.5(9) . . . . ?
C20 C19 C8 C7 166.3(6) . . . . ?
C20 C19 C18 S1 0.4(7) . . . . ?
C5 C4 C3 C2 3.3(10) . . . . ?
C5 C7 C8 N1 -4.4(6) . . . . ?
C5 C7 C8 C19 179.8(5) . . . . ?
C21 S1 C18 C19 -1.3(5) . . . . ?
C10 N2 C11 C12 177.3(5) . . . . ?
C10 N2 C11 C7 4.3(7) . . . . ?
C10 C9 C7 C11 16.7(6) . . . . ?
C10 C9 C7 C8 146.6(5) . . . . ?
C10 C9 C7 C5 -104.1(5) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
