# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_3ba
_database_code_depnum_ccdc_archive 'CCDC 2248071'
loop_
_audit_author_name
_audit_author_address
'Dajun Zhang'
;South China University of Technology
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-05-30 downloaded from the CCDC.
;
_audit_creation_date             2022-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N3 O6 S'
_chemical_formula_sum            'C22 H21 N3 O6 S'
_chemical_formula_weight         455.48
_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 0.0181 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'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.58560(10)
_cell_length_b                   12.11150(10)
_cell_length_c                   21.14980(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2199.25(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17414
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6090
_cell_measurement_theta_min      3.6350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19124
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.765
_diffrn_reflns_theta_min         4.181
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 105.00   0.50    0.05    --  111.82 -96.00 127.00  144
  2  ω     71.00 103.00   0.50    0.05    --  111.82-111.00   0.00   64
  3  ω     37.00  62.00   0.50    0.05    --  111.82-111.00   0.00   50
  4  ω     33.00  79.00   0.50    0.05    --  111.82 -94.00-180.00   92
  5  ω     42.00  67.00   0.50    0.05    --  111.82 -61.00-150.00   50
  6  ω     64.00  99.00   0.50    0.05    --  111.82 -76.00-136.00   70
  7  ω     60.00 101.00   0.50    0.05    --  111.82 -77.00 -60.00   82
  8  ω     40.00  66.00   0.50    0.05    --  111.82 -61.00 -90.00   52
  9  ω     39.00  67.00   0.50    0.05    --  111.82 -61.00 -60.00   56
 10  ω     40.00  66.00   0.50    0.05    --  111.82 -61.00-180.00   52
 11  ω     65.00  91.00   0.50    0.05    --  111.82 -77.00  60.00   52
 12  ω     39.00  65.00   0.50    0.05    --  111.82 -61.00 120.00   52
 13  ω    105.00 131.00   0.50    0.05    --  111.82 179.00-120.00   52
 14  ω     78.00 104.00   0.50    0.05    --  111.82 179.00-120.00   52
 15  ω     90.00 116.00   0.50    0.05    --  111.82  76.00  -9.00   52
 16  ω    124.00 156.00   0.50    0.05    --  111.82  45.00 -90.00   64
 17  ω    150.00 175.00   0.50    0.05    --  111.82  76.00  -9.00   50
 18  ω     84.00 171.00   0.50    0.05    --  111.82  45.00 -60.00  174
 19  ω     95.00 121.00   0.50    0.05    --  111.82  45.00 -90.00   52
 20  ω    140.00 175.00   0.50    0.05    --  111.82  54.00 138.00   70
 21  ω     90.00 126.00   0.50    0.05    --  111.82  54.00 138.00   72
 22  ω     14.00 116.00   0.50    0.05    --   39.45  54.00 138.00  204
 23  ω    -74.00  27.00   0.50    0.05    --  -39.45  76.00  -9.00  202
 24  ω    -38.00  14.00   0.50    0.05    --  -39.45  96.00-123.00  104
 25  ω   -131.00 -92.00   0.50    0.05    --  -52.00 -94.00  90.00   78
 26  ω     45.00  70.00   0.50    0.05    --  111.82 -96.00 127.00   50
 27  ω     71.00  97.00   0.50    0.05    --  111.82 -77.00  90.00   52
 28  ω    -79.00 -53.00   0.50    0.05    --  -39.45 -54.00  -5.00   52
 29  ω    -39.00 -13.00   0.50    0.05    --  -39.45 -54.00  -5.00   52
 30  ω    -27.00   0.00   0.50    0.05    --   39.45 -19.00   0.00   54
 31  ω    -25.00  29.00   0.50    0.05    --  -52.00  15.00 120.00  108
 32  ω    -55.00 -23.00   0.50    0.05    --  -52.00 -61.00-120.00   64
 33  ω   -124.00 -32.00   0.50    0.05    --  -52.00 -61.00-150.00  184
 34  ω     40.00 107.00   0.50    0.05    --  111.82-111.00  90.00  134
 35  ω    128.00 173.00   0.50    0.05    --  111.82  77.00-150.00   90
 36  ω     83.00 115.00   0.50    0.05    --  111.82  61.00-120.00   64
 37  ω     77.00 103.00   0.50    0.05    --  111.82  77.00-150.00   52
 38  ω     47.00  96.00   0.50    0.05    --  111.82-111.00  60.00   98
 39  ω    143.00 174.00   0.50    0.05    --  111.82  45.00-120.00   62
 40  ω     78.00 170.00   0.50    0.05    --  111.82  77.00-180.00  184
 41  ω     41.00  51.50   0.50    0.05    --  111.82 -61.00 -30.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1679963000
_diffrn_orient_matrix_UB_12      0.0330629000
_diffrn_orient_matrix_UB_13      0.0174460000
_diffrn_orient_matrix_UB_21      -0.0068376000
_diffrn_orient_matrix_UB_22      0.0762426000
_diffrn_orient_matrix_UB_23      -0.0581686000
_diffrn_orient_matrix_UB_31      -0.0629623000
_diffrn_orient_matrix_UB_32      -0.0963392000
_diffrn_orient_matrix_UB_33      -0.0401151000
_diffrn_oxdiff_digest_frames     
;
01169126a0c9a1060810295ff560226a5901382c1ab
;
_diffrn_oxdiff_digest_hkl        
;
012fc89a59517553e1bd4632b68bc49f41f39b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4491
_reflns_number_total             4520
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.041
_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)+(0.0400P)²+0.6050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0683
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C2(H2A), C22(H22), C11(H11), C6(H6), C18(H18), C14(H14),
 C19(H19), C3(H3), C12(H12), C21(H21), C5(H5), C4(H4), C13(H13), C20(H20)
;
_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 0.61214(5) 0.84116(3) 0.63096(2) 0.01526(10) Uani 1 1 d . . . . .
O1 O 0.75334(16) 0.50920(10) 0.55767(6) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.80610(16) 0.67418(10) 0.51395(6) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.76625(16) 0.80383(12) 0.64554(6) 0.0221(3) Uani 1 1 d . . . . .
O4 O 0.58381(16) 0.95448(11) 0.61608(6) 0.0211(3) Uani 1 1 d . . . . .
O6 O 0.23912(19) 1.02517(12) 0.69056(8) 0.0333(4) Uani 1 1 d . . . . .
O5 O 0.25763(18) 0.90245(13) 0.61621(7) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.54990(17) 0.76818(12) 0.57234(7) 0.0157(3) Uani 1 1 d . . . . .
H2 H 0.505038 0.800187 0.539727 0.019 Uiso 1 1 calc R . . . .
N3 N 0.2811(2) 0.93559(14) 0.67010(8) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.28268(19) 0.61681(13) 0.55545(8) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.218562 0.649132 0.528780 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7241(2) 0.61494(15) 0.54562(8) 0.0156(3) Uani 1 1 d . . . . .
C8 C 0.5689(2) 0.64861(15) 0.57405(8) 0.0155(3) Uani 1 1 d . . . . .
H8 H 0.563394 0.622548 0.618864 0.019 Uiso 1 1 calc R . . . .
C1 C 0.2296(2) 0.59180(15) 0.61589(9) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.2993(2) 0.51130(17) 0.65370(10) 0.0230(4) Uani 1 1 d . . . . .
H2A H 0.389692 0.473803 0.639240 0.028 Uiso 1 1 calc R . . . .
C10 C 0.4977(2) 0.80701(15) 0.69890(8) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.3595(2) 0.86056(15) 0.71446(9) 0.0195(4) Uani 1 1 d . . . . .
C16 C 0.8900(2) 0.46294(15) 0.52542(9) 0.0205(4) Uani 1 1 d . . . . .
H16A H 0.985076 0.504295 0.537255 0.025 Uiso 1 1 calc R . . . .
H16B H 0.876687 0.467262 0.478990 0.025 Uiso 1 1 calc R . . . .
C22 C 1.0036(2) 0.31611(16) 0.59473(9) 0.0219(4) Uani 1 1 d . . . . .
H22 H 1.065131 0.371275 0.614614 0.026 Uiso 1 1 calc R . . . .
C11 C 0.5587(2) 0.73201(16) 0.74220(10) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.652845 0.694221 0.732743 0.027 Uiso 1 1 calc R . . . .
C17 C 0.9027(2) 0.34485(15) 0.54612(8) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.0960(2) 0.64556(16) 0.63877(10) 0.0238(4) Uani 1 1 d . . . . .
H6 H 0.047077 0.700694 0.613755 0.029 Uiso 1 1 calc R . . . .
C18 C 0.8116(2) 0.26368(16) 0.51779(9) 0.0226(4) Uani 1 1 d . . . . .
H18 H 0.742557 0.282881 0.484468 0.027 Uiso 1 1 calc R . . . .
C14 C 0.2863(3) 0.84455(19) 0.77197(10) 0.0282(4) Uani 1 1 d . . . . .
H14 H 0.194493 0.884480 0.782271 0.034 Uiso 1 1 calc R . . . .
C7 C 0.4383(2) 0.59185(16) 0.53487(9) 0.0195(4) Uani 1 1 d . . . . .
H7A H 0.449235 0.614475 0.490110 0.023 Uiso 1 1 calc R . . . .
H7B H 0.453692 0.510915 0.536855 0.023 Uiso 1 1 calc R . . . .
C19 C 0.8211(3) 0.15479(18) 0.53798(10) 0.0264(4) Uani 1 1 d . . . . .
H19 H 0.757486 0.099933 0.518924 0.032 Uiso 1 1 calc R . . . .
C3 C 0.2365(3) 0.48597(18) 0.71244(10) 0.0287(5) Uani 1 1 d . . . . .
H3 H 0.284961 0.431028 0.737762 0.034 Uiso 1 1 calc R . . . .
C12 C 0.4831(3) 0.71200(18) 0.79910(10) 0.0289(4) Uani 1 1 d . . . . .
H12 H 0.523682 0.658735 0.827663 0.035 Uiso 1 1 calc R . . . .
C21 C 1.0149(3) 0.20673(18) 0.61442(10) 0.0264(4) Uani 1 1 d . . . . .
H21 H 1.085008 0.187256 0.647320 0.032 Uiso 1 1 calc R . . . .
C5 C 0.0351(2) 0.6190(2) 0.69739(11) 0.0304(5) Uani 1 1 d . . . . .
H5 H -0.055502 0.655878 0.712127 0.036 Uiso 1 1 calc R . . . .
C4 C 0.1049(3) 0.5391(2) 0.73491(10) 0.0327(5) Uani 1 1 d . . . . .
H4 H 0.063112 0.521128 0.775217 0.039 Uiso 1 1 calc R . . . .
C13 C 0.3488(3) 0.7694(2) 0.81435(11) 0.0314(5) Uani 1 1 d . . . . .
H13 H 0.299403 0.757289 0.853943 0.038 Uiso 1 1 calc R . . . .
C20 C 0.9237(3) 0.12608(16) 0.58604(10) 0.0272(5) Uani 1 1 d . . . . .
H20 H 0.931482 0.051419 0.599451 0.033 Uiso 1 1 calc R . . . .


_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 O3 1.4318(14) . ?
S1 O4 1.4289(13) . ?
S1 N2 1.6137(15) . ?
S1 C10 1.7891(19) . ?
O1 C9 1.330(2) . ?
O1 C16 1.468(2) . ?
O2 C9 1.208(2) . ?
O6 N3 1.222(2) . ?
O5 N3 1.225(2) . ?
N2 H2 0.8800 . ?
N2 C8 1.458(2) . ?
N3 C15 1.469(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.390(2) . ?
N1 C7 1.437(3) . ?
C9 C8 1.518(2) . ?
C8 H8 1.0000 . ?
C8 C7 1.554(2) . ?
C1 C2 1.396(3) . ?
C1 C6 1.405(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.388(3) . ?
C10 C15 1.392(3) . ?
C10 C11 1.392(3) . ?
C15 C14 1.383(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.500(2) . ?
C22 H22 0.9500 . ?
C22 C17 1.388(3) . ?
C22 C21 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C17 C18 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.385(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C20 H20 0.9500 . ?

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
O3 S1 N2 107.36(8) . . ?
O3 S1 C10 105.17(9) . . ?
O4 S1 O3 120.53(9) . . ?
O4 S1 N2 107.48(8) . . ?
O4 S1 C10 107.79(8) . . ?
N2 S1 C10 107.97(8) . . ?
C9 O1 C16 115.42(14) . . ?
S1 N2 H2 120.4 . . ?
C8 N2 S1 119.21(12) . . ?
C8 N2 H2 120.4 . . ?
O6 N3 O5 124.86(18) . . ?
O6 N3 C15 117.25(17) . . ?
O5 N3 C15 117.83(16) . . ?
C1 N1 H1 118.8 . . ?
C1 N1 C7 122.49(16) . . ?
C7 N1 H1 118.8 . . ?
O1 C9 C8 110.39(15) . . ?
O2 C9 O1 124.65(17) . . ?
O2 C9 C8 124.88(16) . . ?
N2 C8 C9 110.80(15) . . ?
N2 C8 H8 109.4 . . ?
N2 C8 C7 110.22(15) . . ?
C9 C8 H8 109.4 . . ?
C9 C8 C7 107.64(14) . . ?
C7 C8 H8 109.4 . . ?
N1 C1 C2 122.58(18) . . ?
N1 C1 C6 118.90(17) . . ?
C2 C1 C6 118.44(18) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.06(19) . . ?
C3 C2 H2A 120.0 . . ?
C15 C10 S1 123.39(14) . . ?
C15 C10 C11 117.99(18) . . ?
C11 C10 S1 118.19(15) . . ?
C10 C15 N3 121.85(16) . . ?
C14 C15 N3 116.12(18) . . ?
C14 C15 C10 122.02(18) . . ?
O1 C16 H16A 110.4 . . ?
O1 C16 H16B 110.4 . . ?
O1 C16 C17 106.66(15) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C17 C22 H22 119.9 . . ?
C17 C22 C21 120.23(19) . . ?
C21 C22 H22 119.9 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C22 C17 C16 120.06(17) . . ?
C22 C17 C18 119.48(17) . . ?
C18 C17 C16 120.46(17) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.62(19) . . ?
C5 C6 H6 119.7 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.36(19) . . ?
C19 C18 H18 119.8 . . ?
C15 C14 H14 120.5 . . ?
C15 C14 C13 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
N1 C7 C8 114.58(15) . . ?
N1 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.08(19) . . ?
C20 C21 H21 120.0 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.84(19) . . ?
C21 C20 H20 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.88 2.07 2.863(2) 148.8 4_466
N1 H1 O2 0.88 2.44 2.933(2) 115.8 4_466

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 N2 C8 C9 -89.12(16) . . . . ?
S1 N2 C8 C7 151.84(13) . . . . ?
S1 C10 C15 N3 11.6(3) . . . . ?
S1 C10 C15 C14 -169.77(16) . . . . ?
S1 C10 C11 C12 172.71(16) . . . . ?
O1 C9 C8 N2 168.59(14) . . . . ?
O1 C9 C8 C7 -70.83(18) . . . . ?
O1 C16 C17 C22 -97.4(2) . . . . ?
O1 C16 C17 C18 81.3(2) . . . . ?
O2 C9 C8 N2 -14.7(2) . . . . ?
O2 C9 C8 C7 105.9(2) . . . . ?
O3 S1 N2 C8 47.02(15) . . . . ?
O3 S1 C10 C15 156.70(15) . . . . ?
O3 S1 C10 C11 -15.69(17) . . . . ?
O4 S1 N2 C8 178.06(13) . . . . ?
O4 S1 C10 C15 26.92(18) . . . . ?
O4 S1 C10 C11 -145.46(15) . . . . ?
O6 N3 C15 C10 -132.2(2) . . . . ?
O6 N3 C15 C14 49.1(2) . . . . ?
O5 N3 C15 C10 50.4(3) . . . . ?
O5 N3 C15 C14 -128.3(2) . . . . ?
N2 S1 C10 C15 -88.91(17) . . . . ?
N2 S1 C10 C11 98.71(16) . . . . ?
N2 C8 C7 N1 -58.3(2) . . . . ?
N3 C15 C14 C13 175.9(2) . . . . ?
N1 C1 C2 C3 -176.78(18) . . . . ?
N1 C1 C6 C5 176.78(19) . . . . ?
C9 O1 C16 C17 179.20(15) . . . . ?
C9 C8 C7 N1 -179.20(15) . . . . ?
C1 N1 C7 C8 -60.2(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C10 S1 N2 C8 -65.91(15) . . . . ?
C10 C15 C14 C13 -2.8(3) . . . . ?
C10 C11 C12 C13 -2.3(3) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C15 C14 C13 C12 0.3(3) . . . . ?
C16 O1 C9 O2 -4.6(3) . . . . ?
C16 O1 C9 C8 172.12(14) . . . . ?
C16 C17 C18 C19 -178.59(18) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C22 C21 C20 C19 -0.1(3) . . . . ?
C11 C10 C15 N3 -175.99(17) . . . . ?
C11 C10 C15 C14 2.6(3) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C17 C22 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C7 N1 C1 C2 -21.6(3) . . . . ?
C7 N1 C1 C6 161.69(17) . . . . ?
C21 C22 C17 C16 179.49(18) . . . . ?
C21 C22 C17 C18 0.8(3) . . . . ?

_shelx_SHELXL_version_number     2016/6

_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 1.453
_oxdiff_exptl_absorpt_empirical_full_min 0.743
