# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_9A
_database_code_depnum_ccdc_archive 'CCDC 2360991'
loop_
_audit_author_name
_audit_author_address
'Kenta Kato'
;Waseda University
Japan
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N7 O4 S'
_chemical_formula_sum            'C17 H13 N7 O4 S'
_chemical_formula_weight         411.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   17.5466(5)
_cell_length_b                   4.9289(2)
_cell_length_c                   23.3375(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.338(3)
_cell_angle_gamma                90
_cell_volume                     2001.82(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5129
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      74.8680
_cell_measurement_theta_min      2.9910
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.457
_exptl_absorpt_coefficient_mu    1.785
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 -12 0.0311
-3 3 1 0.2255
5 0 12 0.0218
-2 -3 -7 0.2263
10 0 -8 0.0191
-10 0 8 0.0191

_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.4159 -0.1474 -12.2664 -0.2789 -0.7988 0.5330
-3.1883 3.0722 0.6991 -0.2020 -0.5628 -0.8015
5.4989 0.0517 12.2089 0.2844 0.8139 -0.5066
-2.4036 -2.7448 -6.6115 -0.1706 0.0264 0.9850
10.3901 -0.0560 -7.9404 0.9743 -0.1259 0.1869
-10.3901 0.0560 7.9404 -0.9743 0.1259 -0.1869

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10617
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.155
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  68.00   0.50    2.42    --  108.01 -61.00  90.00   50
  2  ω     38.00  63.00   0.50    2.42    --  108.01 -61.00  60.00   50
  3  ω     36.00  61.00   0.50    2.42    --  108.01 -61.00 -30.00   50
  4  ω     34.00  65.00   0.50    2.42    --  108.01 -61.00  30.00   62
  5  ω     34.00 100.00   0.50    2.42    --  108.01 -77.00-120.00  132
  6  ω     39.00  68.00   0.50    2.42    --  108.01 -61.00 -90.00   58
  7  ω     43.00  68.00   0.50    2.42    --  108.01 -61.00-120.00   50
  8  ω     36.00  66.00   0.50    2.42    --  108.01 -61.00-180.00   60
  9  ω     10.00  38.00   0.50    0.60    --   42.80 -43.00-158.00   56
 10  ω     70.00  96.00   0.50    0.60    --   42.80  43.00  -6.00   52
 11  ω     95.00 173.00   0.50    2.42    --  108.01  43.00  -6.00  156
 12  ω     70.00 117.00   0.50    0.60    --   42.80 178.00 120.00   94
 13  ω    -46.00 -20.00   0.50    2.42    --  -96.00  45.00 120.00   52
 14  ω    -47.00 -20.00   0.50    2.42    --  -96.00  45.00 150.00   54
 15  ω    -50.00 -24.00   0.50    2.42    --  -96.00  45.00  90.00   52
 16  ω    -49.00  33.00   0.50    0.60    --  -42.80  43.00  -6.00  164
 17  ω    -48.00 -22.00   0.50    2.42    --  -96.00  43.00  -6.00   52
 18  ω    -50.00 -24.00   0.50    2.42    --  -96.00  45.00 -30.00   52
 19  ω    -67.00 -25.00   0.50    2.42    --  -96.00  61.00-180.00   84
 20  ω   -118.00 -20.00   0.50    0.60    --  -42.80 -43.00-158.00  196
 21  ω   -172.00-147.00   0.50    2.42    --  -96.00 -43.00-158.00   50
 22  ω   -107.00 -74.00   0.50    2.42    --  -96.00 -43.00-158.00   66
 23  ω   -177.00-148.00   0.50    2.42    --  -96.00 -15.00  90.00   58
 24  ω   -129.00 -76.00   0.50    2.42    --  -96.00 -15.00  90.00  106
 25  ω    -71.00 -46.00   0.50    2.42    --  -96.00 -15.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0830390000
_diffrn_orient_matrix_UB_12      0.0236512000
_diffrn_orient_matrix_UB_13      -0.0142090000
_diffrn_orient_matrix_UB_21      0.0286236000
_diffrn_orient_matrix_UB_22      -0.1658970000
_diffrn_orient_matrix_UB_23      0.0544756000
_diffrn_orient_matrix_UB_31      -0.0106345000
_diffrn_orient_matrix_UB_32      -0.2638225000
_diffrn_orient_matrix_UB_33      -0.0355905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3238
_reflns_number_total             3814
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1127P)²+1.1182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.1746
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
1.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C16(H16), C11(H11), C10(H10), C7(H7), C9(H9), C8(H8)
1.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.67501(3) 0.69004(13) 0.73297(2) 0.0296(2) Uani 1 1 d . . . . .
O1 O 0.81793(11) 0.3684(4) 0.56192(8) 0.0375(5) Uani 1 1 d . . . . .
O3 O 0.71859(11) -0.5225(4) 0.41189(8) 0.0394(5) Uani 1 1 d . . . . .
O4 O 0.60214(13) -0.4286(4) 0.37579(8) 0.0452(5) Uani 1 1 d . . . . .
N1 N 0.56067(13) 0.8967(4) 0.65732(9) 0.0302(5) Uani 1 1 d . . . . .
N4 N 0.69030(12) 0.3837(5) 0.63178(8) 0.0291(5) Uani 1 1 d . . . . .
N3 N 0.64486(12) 0.4097(4) 0.57986(8) 0.0286(5) Uani 1 1 d . . . . .
N2 N 0.58746(13) 0.5972(4) 0.57769(8) 0.0298(5) Uani 1 1 d . . . . .
O2 O 0.81796(14) -0.0284(5) 0.60148(10) 0.0525(6) Uani 1 1 d . . . . .
N6 N 0.79033(13) 0.1463(5) 0.56839(9) 0.0316(5) Uani 1 1 d . . . . .
N5 N 0.57435(13) 1.0823(5) 0.75130(9) 0.0311(5) Uani 1 1 d . . . . .
N7 N 0.65988(14) -0.3869(5) 0.41003(9) 0.0333(5) Uani 1 1 d . . . . .
C2 C 0.59801(15) 0.7011(5) 0.63062(10) 0.0289(5) Uani 1 1 d . . . . .
C12 C 0.65066(14) 0.2265(5) 0.53488(10) 0.0271(5) Uani 1 1 d . . . . .
C13 C 0.71797(15) 0.0804(5) 0.53126(10) 0.0291(5) Uani 1 1 d . . . . .
C3 C 0.66081(14) 0.5672(5) 0.66307(10) 0.0281(5) Uani 1 1 d . . . . .
C14 C 0.72223(15) -0.1217(5) 0.49157(10) 0.0299(5) Uani 1 1 d . . . . .
H14 H 0.767584 -0.226534 0.491134 0.036 Uiso 1 1 calc R U . . .
C17 C 0.58739(15) 0.1811(5) 0.49314(10) 0.0292(5) Uani 1 1 d . . . . .
H17 H 0.541861 0.284986 0.493564 0.035 Uiso 1 1 calc R U . . .
C1 C 0.59477(14) 0.9146(5) 0.71137(10) 0.0282(5) Uani 1 1 d . . . . .
C15 C 0.65707(15) -0.1672(5) 0.45176(10) 0.0294(5) Uani 1 1 d . . . . .
C16 C 0.59116(15) -0.0151(5) 0.45126(10) 0.0305(5) Uani 1 1 d . . . . .
H16 H 0.548675 -0.044659 0.422397 0.037 Uiso 1 1 calc R U . . .
C4 C 0.60878(16) 1.0575(6) 0.81177(10) 0.0371(6) Uani 1 1 d . . . . .
H4A H 0.588984 0.894282 0.828752 0.056 Uiso 1 1 calc R U . . .
H4B H 0.595589 1.217567 0.833408 0.056 Uiso 1 1 calc R U . . .
H4C H 0.664760 1.044298 0.813545 0.056 Uiso 1 1 calc R U . . .
C5 C 0.50232(16) 1.2385(6) 0.73990(11) 0.0346(6) Uani 1 1 d . . . . .
H5A H 0.490579 1.272844 0.697905 0.042 Uiso 1 1 calc R U . . .
H5B H 0.508740 1.415935 0.759795 0.042 Uiso 1 1 calc R U . . .
C11 C 0.39593(17) 0.8956(6) 0.72543(13) 0.0401(6) Uani 1 1 d . . . . .
H11 H 0.407429 0.869165 0.687133 0.048 Uiso 1 1 calc R U . . .
C6 C 0.43658(16) 1.0868(6) 0.76072(11) 0.0360(6) Uani 1 1 d . . . . .
C10 C 0.33886(18) 0.7436(7) 0.74561(15) 0.0496(8) Uani 1 1 d . . . . .
H10 H 0.311020 0.614166 0.721050 0.060 Uiso 1 1 calc R U . . .
C7 C 0.41836(18) 1.1264(8) 0.81627(14) 0.0510(8) Uani 1 1 d . . . . .
H7 H 0.445095 1.259512 0.840496 0.061 Uiso 1 1 calc R U . . .
C9 C 0.32204(19) 0.7791(9) 0.80161(17) 0.0575(9) Uani 1 1 d . . . . .
H9 H 0.283738 0.671131 0.815864 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3615(2) 0.9729(10) 0.83649(16) 0.0639(11) Uani 1 1 d . . . . .
H8 H 0.349443 1.000864 0.874594 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 C3 1.728(2) . ?
S1 C1 1.811(3) . ?
O1 N6 1.214(3) . ?
O3 N7 1.224(3) . ?
O4 N7 1.225(3) . ?
N1 C2 1.361(3) . ?
N1 C1 1.328(3) . ?
N4 N3 1.369(3) . ?
N4 C3 1.310(3) . ?
N3 N2 1.363(3) . ?
N3 C12 1.398(3) . ?
N2 C2 1.328(3) . ?
O2 N6 1.216(3) . ?
N6 C13 1.479(3) . ?
N5 C1 1.328(3) . ?
N5 C4 1.468(3) . ?
N5 C5 1.475(3) . ?
N7 C15 1.462(3) . ?
C2 C3 1.418(3) . ?
C12 C13 1.395(4) . ?
C12 C17 1.398(3) . ?
C13 C14 1.369(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.382(4) . ?
C15 C16 1.377(4) . ?
C16 H16 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.506(4) . ?
C11 H11 0.9500 . ?
C11 C6 1.387(4) . ?
C11 C10 1.381(5) . ?
C6 C7 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.387(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.382(6) . ?
C8 H8 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
C3 S1 C1 86.46(11) . . ?
C1 N1 C2 107.3(2) . . ?
C3 N4 N3 101.7(2) . . ?
N4 N3 C12 120.9(2) . . ?
N2 N3 N4 116.14(19) . . ?
N2 N3 C12 122.29(19) . . ?
C2 N2 N3 102.3(2) . . ?
O1 N6 O2 125.8(2) . . ?
O1 N6 C13 116.8(2) . . ?
O2 N6 C13 117.4(2) . . ?
C1 N5 C4 120.5(2) . . ?
C1 N5 C5 120.0(2) . . ?
C4 N5 C5 117.1(2) . . ?
O3 N7 O4 123.6(2) . . ?
O3 N7 C15 118.7(2) . . ?
O4 N7 C15 117.6(2) . . ?
N1 C2 C3 118.2(2) . . ?
N2 C2 N1 132.9(2) . . ?
N2 C2 C3 108.9(2) . . ?
N3 C12 C17 119.9(2) . . ?
C13 C12 N3 121.5(2) . . ?
C13 C12 C17 118.6(2) . . ?
C12 C13 N6 121.4(2) . . ?
C14 C13 N6 116.0(2) . . ?
C14 C13 C12 122.4(2) . . ?
N4 C3 S1 138.48(19) . . ?
N4 C3 C2 111.0(2) . . ?
C2 C3 S1 110.47(18) . . ?
C13 C14 H14 121.4 . . ?
C13 C14 C15 117.1(2) . . ?
C15 C14 H14 121.4 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
N1 C1 S1 117.62(19) . . ?
N5 C1 S1 117.04(17) . . ?
N5 C1 N1 125.3(2) . . ?
C14 C15 N7 117.9(2) . . ?
C16 C15 N7 119.8(2) . . ?
C16 C15 C14 122.3(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
N5 C4 H4A 109.5 . . ?
N5 C4 H4B 109.5 . . ?
N5 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
N5 C5 C6 110.9(2) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C6 120.4(3) . . ?
C11 C6 C5 120.2(3) . . ?
C11 C6 C7 119.2(3) . . ?
C7 C6 C5 120.6(3) . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?

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
O1 N6 C13 C12 -63.6(3) . . . . ?
O1 N6 C13 C14 113.3(3) . . . . ?
O3 N7 C15 C14 0.5(3) . . . . ?
O3 N7 C15 C16 -178.8(2) . . . . ?
O4 N7 C15 C14 178.9(2) . . . . ?
O4 N7 C15 C16 -0.4(4) . . . . ?
N1 C2 C3 S1 0.5(3) . . . . ?
N1 C2 C3 N4 179.5(2) . . . . ?
N4 N3 N2 C2 1.6(3) . . . . ?
N4 N3 C12 C13 -24.6(4) . . . . ?
N4 N3 C12 C17 153.7(2) . . . . ?
N3 N4 C3 S1 178.9(2) . . . . ?
N3 N4 C3 C2 0.4(3) . . . . ?
N3 N2 C2 N1 -179.9(3) . . . . ?
N3 N2 C2 C3 -1.2(3) . . . . ?
N3 C12 C13 N6 -10.9(4) . . . . ?
N3 C12 C13 C14 172.4(2) . . . . ?
N3 C12 C17 C16 -175.0(2) . . . . ?
N2 N3 C12 C13 164.9(2) . . . . ?
N2 N3 C12 C17 -16.9(4) . . . . ?
N2 C2 C3 S1 -178.41(18) . . . . ?
N2 C2 C3 N4 0.5(3) . . . . ?
O2 N6 C13 C12 118.3(3) . . . . ?
O2 N6 C13 C14 -64.8(3) . . . . ?
N6 C13 C14 C15 -173.0(2) . . . . ?
N5 C5 C6 C11 -85.5(3) . . . . ?
N5 C5 C6 C7 91.3(3) . . . . ?
N7 C15 C16 C17 176.0(2) . . . . ?
C2 N1 C1 S1 -0.3(3) . . . . ?
C2 N1 C1 N5 -179.5(3) . . . . ?
C12 N3 N2 C2 172.5(2) . . . . ?
C12 C13 C14 C15 3.8(4) . . . . ?
C12 C17 C16 C15 1.1(4) . . . . ?
C13 C12 C17 C16 3.3(4) . . . . ?
C13 C14 C15 N7 -178.4(2) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C3 S1 C1 N1 0.5(2) . . . . ?
C3 S1 C1 N5 179.8(2) . . . . ?
C3 N4 N3 N2 -1.2(3) . . . . ?
C3 N4 N3 C12 -172.3(2) . . . . ?
C14 C15 C16 C17 -3.2(4) . . . . ?
C17 C12 C13 N6 170.8(2) . . . . ?
C17 C12 C13 C14 -5.9(4) . . . . ?
C1 S1 C3 N4 -179.0(3) . . . . ?
C1 S1 C3 C2 -0.52(19) . . . . ?
C1 N1 C2 N2 178.5(3) . . . . ?
C1 N1 C2 C3 -0.2(3) . . . . ?
C1 N5 C5 C6 91.8(3) . . . . ?
C4 N5 C1 S1 -8.2(3) . . . . ?
C4 N5 C1 N1 171.0(3) . . . . ?
C4 N5 C5 C6 -70.7(3) . . . . ?
C5 N5 C1 S1 -170.05(19) . . . . ?
C5 N5 C1 N1 9.2(4) . . . . ?
C5 C6 C7 C8 -175.5(3) . . . . ?
C11 C6 C7 C8 1.4(5) . . . . ?
C11 C10 C9 C8 1.7(5) . . . . ?
C6 C11 C10 C9 -0.5(5) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C10 C11 C6 C5 175.8(3) . . . . ?
C10 C11 C6 C7 -1.0(4) . . . . ?
C10 C9 C8 C7 -1.4(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.303 0.500 174.5 34.0 ?
2 0.500 -0.843 1.000 174.5 34.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.205
_oxdiff_exptl_absorpt_empirical_full_min 0.565
####################################################################### 
# 
# 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_11N1
_database_code_depnum_ccdc_archive 'CCDC 2360992'
loop_
_audit_author_name
_audit_author_address
'Kenta Kato'
;Waseda University
Japan
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 N5 S'
_chemical_formula_sum            'C19 H23 N5 S'
_chemical_formula_weight         353.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1240(2)
_cell_length_b                   10.0991(3)
_cell_length_c                   14.9338(6)
_cell_angle_alpha                80.551(3)
_cell_angle_beta                 86.987(3)
_cell_angle_gamma                77.131(2)
_cell_volume                     888.07(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6221
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1590
_cell_measurement_theta_min      2.9920
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 0 0.0587
0 -6 2 0.0313
-1 -1 9 0.0042
0 0 -9 0.0286
0 6 5 0.0151
-4 -2 1 0.0657
0 -6 -5 0.0529
4 2 2 0.0681
0 1 -9 0.0290
0 -1 9 0.0114

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.7311 0.8116 -0.4385 0.1197 0.4873 -0.8650
-0.4313 -6.0064 2.2714 -0.2208 -0.9314 -0.2894
-1.2078 -0.9607 8.7985 -0.8755 -0.1618 -0.4552
0.1773 0.3876 -9.4400 0.9623 0.1791 0.2049
0.1579 6.0893 4.5895 -0.4758 0.8720 0.1150
-3.9046 -1.8269 1.1008 -0.0330 0.0689 -0.9971
-0.2263 -6.1163 -4.5664 0.4748 -0.8701 -0.1324
3.9308 2.0808 1.7145 -0.2558 -0.0720 0.9641
0.3041 1.1222 -9.1336 0.9280 0.2776 0.2486
0.0725 -0.9169 9.2400 -0.9466 -0.2827 -0.1551

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_min         3.000
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00 -23.00   0.50    1.40    --  -96.00  61.00-180.00   72
  2  ω    -62.00 -33.00   0.50    1.40    --  -96.00  61.00-150.00   58
  3  ω    -50.00 -21.00   0.50    1.40    --  -96.00  45.00-120.00   58
  4  ω    -70.00 -45.00   0.50    1.40    --  -96.00  61.00-120.00   50
  5  ω    -48.00 -22.00   0.50    1.40    --  -96.00  45.00 -90.00   52
  6  ω    -59.00 -24.00   0.50    1.40    --  -96.00  61.00  90.00   70
  7  ω      8.00  34.00   0.50    0.40    --  -42.99  38.00  90.00   52
  8  ω    -41.00 -16.00   0.50    0.40    --  -42.99  38.00  90.00   50
  9  ω    -23.00  13.00   0.50    0.40    --  -42.99  19.00  30.00   72
 10  ω     14.00 116.00   0.50    0.40    --   42.99  77.00-120.00  204
 11  ω    123.00 175.00   0.50    1.40    --  108.01 116.00-127.00  104
 12  ω     69.00  94.00   0.50    0.40    --   42.99 167.00  18.00   50
 13  ω     86.00 111.00   0.50    1.40    --  108.01 167.00  18.00   50
 14  ω     88.00 177.00   0.50    1.40    --  108.01  61.00  60.00  178
 15  ω     36.00  61.00   0.50    1.40    --  108.01 -61.00   0.00   50
 16  ω     38.00  65.00   0.50    1.40    --  108.01 -77.00   0.00   54
 17  ω     34.00  79.00   0.50    1.40    --  108.01 -77.00 -60.00   90
 18  ω     72.00 100.00   0.50    1.40    --  108.01 -77.00   0.00   56
 19  ω     74.00  99.00   0.50    1.40    --  108.01 -77.00 120.00   50
 20  ω     35.00  60.00   0.50    1.40    --  108.01 -77.00 120.00   50
 21  ω     37.00  64.00   0.50    1.40    --  108.01 -95.00 150.00   54
 22  ω     81.00 108.00   0.50    1.40    --  108.01-116.00 143.00   54
 23  ω     28.00  73.00   0.50    0.40    --   42.99-116.00 143.00   90
 24  ω     82.00 107.00   0.50    0.40    --   42.99-167.00  -2.00   50
 25  ω    102.00 141.00   0.50    1.40    --  108.01-167.00  -2.00   78
 26  ω     51.00  85.00   0.50    1.40    --  108.01 -95.00 -90.00   68
 27  ω     63.00 104.00   0.50    1.40    --  108.01 -95.00 -60.00   82
 28  ω     74.00 106.00   0.50    1.40    --  108.01 -98.00  -5.61   64
 29  ω     36.00  63.00   0.50    1.40    --  108.01 -98.00  -5.61   54
 30  ω     77.00 106.00   0.50    1.40    --  108.01 -95.00 150.00   58
 31  ω    -83.00  -7.00   0.50    0.40    --  -42.99 116.00-127.00  152
 32  ω    -58.00 -28.00   0.50    1.40    --  -96.00 116.00-127.00   60
 33  ω    -92.00 -66.00   0.50    0.40    --  -42.99 167.00  18.00   52
 34  ω    -58.00 -25.00   0.50    1.40    --  -96.00 125.00  30.00   66
 35  ω   -177.00 -53.00   0.50    1.40    --  -96.00 -15.00 -30.00  248
 36  ω   -133.00 -75.00   0.50    1.40    --  -96.00 -45.00-150.00  116
 37  ω    -63.00 -21.00   0.50    0.40    --  -42.99 -38.00 120.00   84
 38  ω   -118.00 -70.00   0.50    0.40    --  -42.99 -38.00 120.00   96
 39  ω   -124.00 -99.00   0.50    1.40    --  -96.00-116.00 143.00   50
 40  ω    -80.00 -46.00   0.50    0.40    --  -42.99-167.00  -2.00   68
 41  ω    -71.00 -46.00   0.50    1.40    --  -96.00-167.00  -2.00   50
 42  ω   -103.00 -78.00   0.50    1.40    --  -96.00-167.00  -2.00   50
 43  ω   -135.00-109.00   0.50    1.40    --  -96.00-167.00  -2.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0201721000
_diffrn_orient_matrix_UB_12      -0.0004879000
_diffrn_orient_matrix_UB_13      -0.1023326000
_diffrn_orient_matrix_UB_21      -0.0948990000
_diffrn_orient_matrix_UB_22      0.1564619000
_diffrn_orient_matrix_UB_23      -0.0143285000
_diffrn_orient_matrix_UB_31      0.2391456000
_diffrn_orient_matrix_UB_32      0.0248895000
_diffrn_orient_matrix_UB_33      -0.0161961000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3077
_reflns_number_total             3432
_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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.065
_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)+(0.0475P)²+0.3074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C5(H5)
1.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B),
 C4(H4A,H4B), C7(H7A,H7B), C6(H6A,H6B)
1.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C19(H19), C18(H18), C17(H17)
;
_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 0.81624(5) 0.43606(3) 0.86847(2) 0.02407(12) Uani 1 1 d . . . . .
N3 N 0.4602(2) 0.74449(12) 0.94909(8) 0.0236(3) Uani 1 1 d . . . . .
N5 N 0.6451(2) 0.32318(12) 0.71530(8) 0.0218(3) Uani 1 1 d . . . . .
N4 N 0.39175(19) 0.56754(12) 0.85917(8) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.6499(2) 0.76041(13) 0.98573(9) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.8191(2) 0.65954(13) 0.96844(9) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.5095(2) 0.63187(14) 0.90781(9) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.9757(2) 0.24832(14) 0.45781(10) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.7340(2) 0.57974(15) 0.92085(9) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.5351(2) 0.46262(15) 0.83518(9) 0.0220(3) Uani 1 1 d . . . . .
C11 C 0.7995(2) 0.27949(14) 0.53095(10) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.649980 0.300437 0.501696 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6360(2) 0.43929(14) 0.64135(10) 0.0223(3) Uani 1 1 d . . . . .
H9A H 0.652948 0.521155 0.666534 0.027 Uiso 1 1 calc R U . . .
H9B H 0.488092 0.461151 0.612193 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8189(2) 0.40720(14) 0.57073(10) 0.0221(3) Uani 1 1 d . . . . .
H10A H 0.967198 0.391019 0.598876 0.026 Uiso 1 1 calc R U . . .
H10B H 0.806876 0.486863 0.521396 0.026 Uiso 1 1 calc R U . . .
C15 C 0.9188(2) 0.28518(15) 0.36665(10) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.767198 0.325043 0.351198 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4742(2) 0.35992(15) 0.78427(10) 0.0245(3) Uani 1 1 d . . . . .
H8A H 0.460110 0.276339 0.827209 0.029 Uiso 1 1 calc R U . . .
H8B H 0.327806 0.399387 0.754914 0.029 Uiso 1 1 calc R U . . .
C16 C 1.0784(3) 0.26505(15) 0.29776(11) 0.0279(3) Uani 1 1 d . . . . .
H16 H 1.035884 0.291718 0.236041 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8000(3) 0.16120(15) 0.60966(10) 0.0282(3) Uani 1 1 d . . . . .
H12A H 0.775917 0.079801 0.585790 0.034 Uiso 1 1 calc R U . . .
H12B H 0.947723 0.135981 0.639145 0.034 Uiso 1 1 calc R U . . .
C19 C 1.1996(2) 0.18792(15) 0.47828(11) 0.0271(3) Uani 1 1 d . . . . .
H19 H 1.242931 0.160822 0.539894 0.032 Uiso 1 1 calc R U . . .
C18 C 1.3596(2) 0.16710(15) 0.40936(12) 0.0296(3) Uani 1 1 d . . . . .
H18 H 1.511079 0.125884 0.424313 0.036 Uiso 1 1 calc R U . . .
C17 C 1.2998(3) 0.20599(15) 0.31924(11) 0.0294(3) Uani 1 1 d . . . . .
H17 H 1.409782 0.192298 0.272412 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6176(3) 0.20121(15) 0.67949(10) 0.0269(3) Uani 1 1 d . . . . .
H13A H 0.469132 0.220308 0.651064 0.032 Uiso 1 1 calc R U . . .
H13B H 0.623702 0.123648 0.730014 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2477(3) 0.84321(15) 0.95541(11) 0.0278(3) Uani 1 1 d . . . . .
H4A H 0.229740 0.867973 1.017234 0.033 Uiso 1 1 calc R U . . .
H4B H 0.123097 0.799592 0.945693 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2340(3) 0.97145(16) 0.88728(11) 0.0330(4) Uani 1 1 d . . . . .
H5 H 0.326436 1.036263 0.899770 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2024(3) 0.96585(18) 0.78962(12) 0.0347(4) Uani 1 1 d . . . . .
H7A H 0.193642 0.876227 0.773025 0.042 Uiso 1 1 calc R U . . .
H7B H 0.276372 1.024307 0.743555 0.042 Uiso 1 1 calc R U . . .
C6 C 0.0117(3) 1.03611(18) 0.84409(12) 0.0386(4) Uani 1 1 d . . . . .
H6A H -0.114086 0.989645 0.861153 0.046 Uiso 1 1 calc R U . . .
H6B H -0.031327 1.137777 0.831672 0.046 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 C1 1.7252(15) . ?
S1 C3 1.7675(14) . ?
N3 N2 1.3613(17) . ?
N3 C2 1.3500(18) . ?
N3 C4 1.4615(19) . ?
N5 C9 1.4663(18) . ?
N5 C8 1.4602(18) . ?
N5 C13 1.4662(18) . ?
N4 C2 1.3743(18) . ?
N4 C3 1.3034(19) . ?
N2 N1 1.3289(18) . ?
N1 C1 1.3565(19) . ?
C2 C1 1.370(2) . ?
C14 C11 1.5144(19) . ?
C14 C15 1.392(2) . ?
C14 C19 1.399(2) . ?
C3 C8 1.5012(19) . ?
C11 H11 1.0000 . ?
C11 C10 1.5353(19) . ?
C11 C12 1.532(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5157(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.385(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.521(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.392(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(2) . ?
C17 H17 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.499(2) . ?
C5 H5 1.0000 . ?
C5 C7 1.493(2) . ?
C5 C6 1.501(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.500(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 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 S1 C3 87.38(7) . . ?
N2 N3 C4 121.10(12) . . ?
C2 N3 N2 109.07(11) . . ?
C2 N3 C4 129.80(12) . . ?
C8 N5 C9 110.04(11) . . ?
C8 N5 C13 111.35(11) . . ?
C13 N5 C9 110.18(11) . . ?
C3 N4 C2 106.32(12) . . ?
N1 N2 N3 108.96(11) . . ?
N2 N1 C1 106.71(12) . . ?
N3 C2 N4 135.41(13) . . ?
N3 C2 C1 105.22(12) . . ?
C1 C2 N4 119.36(13) . . ?
C15 C14 C11 120.00(13) . . ?
C15 C14 C19 117.82(14) . . ?
C19 C14 C11 122.13(13) . . ?
N1 C1 S1 140.91(11) . . ?
N1 C1 C2 110.04(13) . . ?
C2 C1 S1 109.02(11) . . ?
N4 C3 S1 117.91(10) . . ?
N4 C3 C8 124.02(12) . . ?
C8 C3 S1 118.02(11) . . ?
C14 C11 H11 107.3 . . ?
C14 C11 C10 111.73(11) . . ?
C14 C11 C12 114.78(12) . . ?
C10 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C12 C11 C10 108.17(11) . . ?
N5 C9 H9A 109.3 . . ?
N5 C9 H9B 109.3 . . ?
N5 C9 C10 111.46(11) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 C11 110.77(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.56(14) . . ?
C16 C15 H15 119.2 . . ?
N5 C8 C3 110.48(11) . . ?
N5 C8 H8A 109.6 . . ?
N5 C8 H8B 109.6 . . ?
C3 C8 H8A 109.6 . . ?
C3 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.88(14) . . ?
C17 C16 H16 120.1 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.19(12) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.71(14) . . ?
C18 C19 H19 119.6 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.49(14) . . ?
C17 C18 H18 119.8 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.54(14) . . ?
C18 C17 H17 120.2 . . ?
N5 C13 C12 111.05(11) . . ?
N5 C13 H13A 109.4 . . ?
N5 C13 H13B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N3 C4 H4A 109.1 . . ?
N3 C4 H4B 109.1 . . ?
N3 C4 C5 112.36(12) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5 116.1 . . ?
C4 C5 C6 117.56(15) . . ?
C7 C5 C4 119.09(14) . . ?
C7 C5 H5 116.1 . . ?
C7 C5 C6 60.12(11) . . ?
C6 C5 H5 116.1 . . ?
C5 C7 H7A 117.8 . . ?
C5 C7 H7B 117.8 . . ?
C5 C7 C6 60.20(11) . . ?
H7A C7 H7B 114.9 . . ?
C6 C7 H7A 117.8 . . ?
C6 C7 H7B 117.8 . . ?
C5 C6 H6A 117.8 . . ?
C5 C6 H6B 117.8 . . ?
C7 C6 C5 59.68(11) . . ?
C7 C6 H6A 117.8 . . ?
C7 C6 H6B 117.8 . . ?
H6A C6 H6B 114.9 . . ?

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 C3 C8 N5 -43.14(15) . . . . ?
N3 N2 N1 C1 -0.19(15) . . . . ?
N3 C2 C1 S1 -178.89(9) . . . . ?
N3 C2 C1 N1 -0.41(16) . . . . ?
N3 C4 C5 C7 73.09(18) . . . . ?
N3 C4 C5 C6 142.43(14) . . . . ?
N5 C9 C10 C11 58.32(15) . . . . ?
N4 C2 C1 S1 0.14(16) . . . . ?
N4 C2 C1 N1 178.63(12) . . . . ?
N4 C3 C8 N5 139.41(14) . . . . ?
N2 N3 C2 N4 -178.52(15) . . . . ?
N2 N3 C2 C1 0.28(15) . . . . ?
N2 N3 C4 C5 78.87(17) . . . . ?
N2 N1 C1 S1 178.11(14) . . . . ?
N2 N1 C1 C2 0.38(16) . . . . ?
C2 N3 N2 N1 -0.06(15) . . . . ?
C2 N3 C4 C5 -98.98(17) . . . . ?
C2 N4 C3 S1 -0.42(15) . . . . ?
C2 N4 C3 C8 177.04(12) . . . . ?
C14 C11 C10 C9 178.00(11) . . . . ?
C14 C11 C12 C13 -179.74(11) . . . . ?
C14 C15 C16 C17 0.5(2) . . . . ?
C14 C19 C18 C17 0.1(2) . . . . ?
C1 S1 C3 N4 0.44(12) . . . . ?
C1 S1 C3 C8 -177.17(11) . . . . ?
C3 S1 C1 N1 -178.04(18) . . . . ?
C3 S1 C1 C2 -0.29(10) . . . . ?
C3 N4 C2 N3 178.84(15) . . . . ?
C3 N4 C2 C1 0.17(17) . . . . ?
C11 C14 C15 C16 176.42(13) . . . . ?
C11 C14 C19 C18 -176.65(12) . . . . ?
C11 C12 C13 N5 -58.02(16) . . . . ?
C9 N5 C8 C3 -70.74(14) . . . . ?
C9 N5 C13 C12 59.21(15) . . . . ?
C10 C11 C12 C13 54.76(15) . . . . ?
C15 C14 C11 C10 -101.25(15) . . . . ?
C15 C14 C11 C12 135.13(14) . . . . ?
C15 C14 C19 C18 0.7(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C8 N5 C9 C10 177.17(11) . . . . ?
C8 N5 C13 C12 -178.40(12) . . . . ?
C12 C11 C10 C9 -54.72(15) . . . . ?
C19 C14 C11 C10 76.03(17) . . . . ?
C19 C14 C11 C12 -47.59(18) . . . . ?
C19 C14 C15 C16 -1.0(2) . . . . ?
C19 C18 C17 C16 -0.5(2) . . . . ?
C13 N5 C9 C10 -59.68(15) . . . . ?
C13 N5 C8 C3 166.80(12) . . . . ?
C4 N3 N2 N1 -178.31(12) . . . . ?
C4 N3 C2 N4 -0.5(3) . . . . ?
C4 N3 C2 C1 178.33(14) . . . . ?
C4 C5 C7 C6 106.91(17) . . . . ?
C4 C5 C6 C7 -109.43(16) . . . . ?

_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 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.849
