# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_g231207b_auto
_database_code_depnum_ccdc_archive 'CCDC 2402734'
loop_
_audit_author_name
_audit_author_address
'Jiangying Li'
;Suzhou Institute of Nano Tech and Nano Bionics
China
;
_audit_update_record             
;
2024-11-14 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        FYX-HCl-H2O
_chemical_formula_moiety         'Cl, H2 O, C13 H9 N6'
_chemical_formula_sum            'C13 H11 Cl N6 O'
_chemical_formula_weight         302.73
_chemical_melting_point          579.35
_chemical_oxdiff_usercomment     CHONF
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.8673(7)
_cell_length_b                   11.7052(11)
_cell_length_c                   17.4705(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.559(8)
_cell_angle_gamma                90
_cell_volume                     1402.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    222.97(10)
_cell_measurement_theta_max      29.1690
_cell_measurement_theta_min      2.1040
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.317
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      222.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  51.00   1.00    1.00    --   12.72 -99.00 -90.00   27
  2  ω    -64.00  54.00   1.00    1.00    --   12.72 -19.00-180.00  118
  3  ω    -36.00  10.00   1.00    1.00    --  -13.50 -77.00   0.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0885910000
_diffrn_orient_matrix_UB_12      -0.0109226000
_diffrn_orient_matrix_UB_13      0.0211889000
_diffrn_orient_matrix_UB_21      0.0184490000
_diffrn_orient_matrix_UB_22      0.0595406000
_diffrn_orient_matrix_UB_23      0.0023124000
_diffrn_orient_matrix_UB_31      -0.0499679000
_diffrn_orient_matrix_UB_32      0.0027287000
_diffrn_orient_matrix_UB_33      0.0346136000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2286
_reflns_number_total             3647
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.061
_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)+(0.0703P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1703
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C4(H4), C10(H10), C2(H2), C5(H5), C1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.71669(10) 0.00516(6) 0.57959(4) 0.0422(2) Uani 1 1 d . . . . .
O1 O 0.8341(3) 0.93696(19) 0.41536(11) 0.0529(6) Uani 1 1 d G . . . .
H1B H 0.810434 0.958288 0.461107 0.079 Uiso 1 1 d G U . . .
H1C H 0.955734 0.951807 0.410907 0.079 Uiso 1 1 d G U . . .
N3 N 0.6928(3) 0.72556(19) 0.38316(11) 0.0320(5) Uani 1 1 d . . . . .
N4 N 0.5680(3) 0.57665(17) 0.32313(11) 0.0325(5) Uani 1 1 d . . . . .
N2 N 0.7339(3) 0.63722(17) 0.43089(11) 0.0342(5) Uani 1 1 d . . . . .
N5 N 0.3968(3) 0.90456(18) 0.13515(11) 0.0359(5) Uani 1 1 d . . . . .
N1 N 0.6597(3) 0.2177(2) 0.48066(12) 0.0386(5) Uani 1 1 d . . . . .
N6 N 0.4404(4) 1.1659(2) 0.21920(13) 0.0484(6) Uani 1 1 d . . . . .
C6 C 0.6557(3) 0.5495(2) 0.39241(13) 0.0292(5) Uani 1 1 d . . . . .
C3 C 0.6596(3) 0.4339(2) 0.42333(13) 0.0296(5) Uani 1 1 d . . . . .
C7 C 0.5959(3) 0.6885(2) 0.31943(12) 0.0296(5) Uani 1 1 d . . . . .
C11 C 0.4552(3) 0.9465(2) 0.20390(13) 0.0314(5) Uani 1 1 d . . . . .
C8 C 0.5305(3) 0.7637(2) 0.25649(12) 0.0294(5) Uani 1 1 d . . . . .
C9 C 0.4688(4) 0.7176(2) 0.18621(13) 0.0335(6) Uani 1 1 d . . . . .
H9 H 0.470064 0.638162 0.178233 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5245(4) 0.8815(2) 0.26543(13) 0.0330(6) Uani 1 1 d . . . . .
H12 H 0.566242 0.916075 0.311877 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5825(4) 0.3436(2) 0.37947(14) 0.0340(6) Uani 1 1 d . . . . .
H4 H 0.529534 0.356810 0.329709 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4053(4) 0.7914(2) 0.12797(13) 0.0368(6) Uani 1 1 d . . . . .
H10 H 0.365751 0.759332 0.080438 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7390(4) 0.4112(2) 0.49646(14) 0.0361(6) Uani 1 1 d . . . . .
H2 H 0.793294 0.470504 0.526728 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5846(4) 0.2353(2) 0.40965(15) 0.0390(6) Uani 1 1 d . . . . .
H5 H 0.533576 0.173822 0.380561 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4457(4) 1.0691(2) 0.21182(13) 0.0366(6) Uani 1 1 d . . . . .
C1 C 0.7374(4) 0.3021(2) 0.52380(14) 0.0406(6) Uani 1 1 d . . . . .
H1A H 0.791014 0.286113 0.573086 0.049 Uiso 1 1 calc R U . . .
H3 H 0.738(4) 0.794(3) 0.3932(15) 0.044(8) Uiso 1 1 d . . . . .
H1 H 0.658(4) 0.144(3) 0.5025(16) 0.057(9) Uiso 1 1 d . . . . .


_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
O1 H1B 0.8597 . ?
O1 H1C 0.8603 . ?
N3 N2 1.350(3) . ?
N3 C7 1.343(3) . ?
N3 H3 0.88(3) . ?
N4 C6 1.365(3) . ?
N4 C7 1.325(3) . ?
N2 C6 1.328(3) . ?
N5 C11 1.342(3) . ?
N5 C10 1.332(3) . ?
N1 C5 1.338(3) . ?
N1 C1 1.339(4) . ?
N1 H1 0.94(3) . ?
N6 C13 1.141(3) . ?
C6 C3 1.457(3) . ?
C3 C4 1.396(3) . ?
C3 C2 1.392(3) . ?
C7 C8 1.463(3) . ?
C11 C12 1.384(3) . ?
C11 C13 1.444(4) . ?
C8 C9 1.390(3) . ?
C8 C12 1.389(3) . ?
C9 H9 0.9400 . ?
C9 C10 1.390(4) . ?
C12 H12 0.9400 . ?
C4 H4 0.9400 . ?
C4 C5 1.372(3) . ?
C10 H10 0.9400 . ?
C2 H2 0.9400 . ?
C2 C1 1.363(4) . ?
C5 H5 0.9400 . ?
C1 H1A 0.9400 . ?

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
H1B O1 H1C 104.5 . . ?
N2 N3 H3 121.1(19) . . ?
C7 N3 N2 110.3(2) . . ?
C7 N3 H3 128.3(18) . . ?
C7 N4 C6 102.36(19) . . ?
C6 N2 N3 102.2(2) . . ?
C10 N5 C11 115.8(2) . . ?
C5 N1 C1 122.4(2) . . ?
C5 N1 H1 120.3(18) . . ?
C1 N1 H1 117.3(18) . . ?
N4 C6 C3 123.0(2) . . ?
N2 C6 N4 114.9(2) . . ?
N2 C6 C3 122.0(2) . . ?
C4 C3 C6 120.0(2) . . ?
C2 C3 C6 121.2(2) . . ?
C2 C3 C4 118.8(2) . . ?
N3 C7 C8 123.5(2) . . ?
N4 C7 N3 110.3(2) . . ?
N4 C7 C8 126.2(2) . . ?
N5 C11 C12 124.9(2) . . ?
N5 C11 C13 115.9(2) . . ?
C12 C11 C13 119.2(2) . . ?
C9 C8 C7 120.1(2) . . ?
C12 C8 C7 121.5(2) . . ?
C12 C8 C9 118.4(2) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C11 C12 C8 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C8 C12 H12 121.0 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
N5 C10 C9 124.2(2) . . ?
N5 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C3 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
N1 C5 C4 119.7(2) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N6 C13 C11 178.8(3) . . ?
N1 C1 C2 120.2(2) . . ?
N1 C1 H1A 119.9 . . ?
C2 C1 H1A 119.9 . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.88(3) 1.83(3) 2.708(3) 179(3) . yes
N1 H1 Cl1 0.94(3) 2.14(3) 3.044(2) 161(3) . yes

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
N3 N2 C6 N4 0.2(3) . . . . ?
N3 N2 C6 C3 -178.2(2) . . . . ?
N3 C7 C8 C9 166.3(2) . . . . ?
N3 C7 C8 C12 -15.0(4) . . . . ?
N4 C6 C3 C4 4.3(3) . . . . ?
N4 C6 C3 C2 -175.6(2) . . . . ?
N4 C7 C8 C9 -14.5(4) . . . . ?
N4 C7 C8 C12 164.1(2) . . . . ?
N2 N3 C7 N4 0.8(3) . . . . ?
N2 N3 C7 C8 -180.0(2) . . . . ?
N2 C6 C3 C4 -177.4(2) . . . . ?
N2 C6 C3 C2 2.7(3) . . . . ?
N5 C11 C12 C8 -1.5(4) . . . . ?
C6 N4 C7 N3 -0.6(2) . . . . ?
C6 N4 C7 C8 -179.8(2) . . . . ?
C6 C3 C4 C5 -179.1(2) . . . . ?
C6 C3 C2 C1 179.1(2) . . . . ?
C3 C4 C5 N1 0.3(4) . . . . ?
C3 C2 C1 N1 -0.1(4) . . . . ?
C7 N3 N2 C6 -0.5(2) . . . . ?
C7 N4 C6 N2 0.3(3) . . . . ?
C7 N4 C6 C3 178.7(2) . . . . ?
C7 C8 C9 C10 179.2(2) . . . . ?
C7 C8 C12 C11 -178.0(2) . . . . ?
C11 N5 C10 C9 0.2(4) . . . . ?
C8 C9 C10 N5 -0.9(4) . . . . ?
C9 C8 C12 C11 0.7(3) . . . . ?
C12 C8 C9 C10 0.4(3) . . . . ?
C4 C3 C2 C1 -0.8(4) . . . . ?
C10 N5 C11 C12 1.1(4) . . . . ?
C10 N5 C11 C13 -179.9(2) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
C13 C11 C12 C8 179.5(2) . . . . ?
C1 N1 C5 C4 -1.3(4) . . . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: H2O'
####################################################################### 
# 
# 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_37-cr-20241122c_auto
_database_code_depnum_ccdc_archive 'CCDC 2405195'
loop_
_audit_author_name
_audit_author_address
'Jiangying Li'
;Suzhou Institute of NanoTech and NanoBionics
China
;
_audit_update_record             
;
2024-11-25 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-11-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'FYX--H2SO4 II'
_chemical_formula_moiety         'C13 H9 N6, H O4 S'
_chemical_formula_sum            'C13 H10 N6 O4 S'
_chemical_formula_weight         346.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
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           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   25.4485(8)
_cell_length_b                   12.9002(5)
_cell_length_c                   4.46615(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1466.19(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5905
_cell_measurement_temperature    273.00(10)
_cell_measurement_theta_max      72.9530
_cell_measurement_theta_min      3.4570
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    2.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13799
_diffrn_reflns_point_group_measured_fraction_full 0.762
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.570
_diffrn_reflns_theta_min         3.473
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00 -23.00   0.50    0.20    --  -77.79  63.00 120.00   50
  2  ω    -54.00 -27.00   0.50    0.20    --  -77.79  63.00  90.00   54
  3  ω    -56.00 -26.00   0.50    0.20    --  -77.79  63.00   0.00   60
  4  ω    -55.00 -26.00   0.50    0.20    --  -77.79  63.00-150.00   58
  5  ω     64.00 110.00   0.50    0.20    --   93.74  12.00 -90.00   92
  6  ω    106.00 138.00   0.50    0.20    --   93.74  77.00-150.00   64
  7  ω    110.00 142.00   0.50    0.20    --   93.74  77.00 -60.00   64
  8  ω    105.00 131.00   0.50    0.20    --   93.74  63.00 -60.00   52
  9  ω    102.00 140.00   0.50    0.20    --   93.74  50.00 -30.00   76
 10  ω    128.00 154.00   0.50    0.20    --   93.74  12.00 -90.00   52
 11  ω    111.00 138.00   0.50    0.20    --   93.74  77.00  30.00   54
 12  ω     65.00  90.00   0.50    0.20    --   93.74  15.00 116.00   50
 13  ω     39.00  65.00   0.50    0.20    --   51.16  15.00 116.00   52
 14  ω     99.00 136.00   0.50    0.20    --   93.74  77.00  90.00   74
 15  ω    107.00 132.00   0.50    0.20    --   93.74 134.00 155.00   50
 16  ω     97.00 123.00   0.50    0.20    --   93.74 111.00 150.00   52
 17  ω     99.00 124.00   0.50    0.20    --   93.74 111.00-100.00   50
 18  ω    120.00 151.00   0.50    0.20    --   93.74 111.00-150.00   62
 19  ω     -1.00  24.00   0.50    0.20    --   57.24 -45.00   0.00   50
 20  ω     45.00  70.00   0.50    0.20    --   93.74 -77.00   0.00   50
 21  ω     44.00  69.00   0.50    0.20    --   93.74 -77.00  60.00   50
 22  ω     44.00  69.00   0.50    0.20    --   93.74 -77.00 120.00   50
 23  ω     -7.00  26.00   0.50    0.20    --   51.16 -45.00 150.00   66
 24  ω     46.00  71.00   0.50    0.20    --   93.74 -77.00  30.00   50
 25  ω     45.00  70.00   0.50    0.20    --   93.74 -77.00 -30.00   50
 26  ω      0.00  25.00   0.50    0.20    --   57.24 -45.00 -30.00   50
 27  ω     44.00  69.00   0.50    0.20    --   93.74 -77.00-120.00   50
 28  ω     70.00  95.00   0.50    0.20    --   93.74-135.00 -90.00   50
 29  ω     36.00  91.00   0.50    0.20    --   93.74-111.00-180.00  110
 30  ω     46.00  71.00   0.50    0.20    --   93.74-134.00  88.00   50
 31  ω     18.00  43.00   0.50    0.20    --   51.16-111.00 165.00   50
 32  ω     21.00  46.00   0.50    0.20    --   57.24-111.00 165.00   50
 33  ω     46.00  92.00   0.50    0.20    --   93.74-111.00 165.00   92
 34  ω     36.00  66.00   0.50    0.20    --   93.74-111.00-150.00   60
 35  ω     42.00  93.00   0.50    0.20    --   93.74 -91.00-180.00  102
 36  ω     50.00  84.00   0.50    0.20    --   93.74 -91.00-150.00   68
 37  ω     51.00  87.00   0.50    0.20    --   93.74 -91.00-120.00   72
 38  ω     41.00  90.00   0.50    0.20    --   93.74 -91.00 120.00   98
 39  ω     53.00  78.00   0.50    0.20    --   98.00 -83.00  82.55   50
 40  ω   -100.00 -73.00   0.50    0.20    --  -77.79 135.00 -24.00   54
 41  ω    -73.00 -48.00   0.50    0.20    --  -58.89 111.00-100.00   50
 42  ω    -78.00 -21.00   0.50    0.20    --  -77.79 111.00-100.00  114
 43  ω   -128.00 -38.00   0.50    0.20    --  -77.79 -15.00 -53.00  180
 44  ω    -97.00 -49.00   0.50    0.20    --  -52.00 -15.00 -53.00   96
 45  ω   -118.00 -93.00   0.50    0.20    --  -77.79-134.00  88.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0501846000
_diffrn_orient_matrix_UB_12      0.0635076000
_diffrn_orient_matrix_UB_13      0.0598069000
_diffrn_orient_matrix_UB_21      0.0315590000
_diffrn_orient_matrix_UB_22      -0.1011321000
_diffrn_orient_matrix_UB_23      0.0363902000
_diffrn_orient_matrix_UB_31      0.0122809000
_diffrn_orient_matrix_UB_32      0.0003196000
_diffrn_orient_matrix_UB_33      -0.3377400000
_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         0.333
_reflns_Friedel_fraction_full    0.448
_reflns_Friedel_fraction_max     0.433
_reflns_number_gt                2092
_reflns_number_total             2268
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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         0.456
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.082
_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)+(0.0762P)²+0.4526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), C3(H3A), C4(H4), C6(H6A), C10(H10), C11(H11), C12(H12),
 C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(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
N1 N 0.95199(15) 0.4075(4) 0.6304(14) 0.0813(16) Uani 1 1 d . . . . .
N2 N 0.83111(13) 0.4944(2) 0.8003(9) 0.0502(8) Uani 1 1 d . . . . .
N3 N 0.74781(10) 0.2387(2) 0.0386(8) 0.0392(7) Uani 1 1 d . . . . .
H3 H 0.779430 0.216018 0.020804 0.047 Uiso 1 1 calc R U . . .
N4 N 0.70623(10) 0.2034(2) -0.1189(8) 0.0413(7) Uani 1 1 d . . . . .
N5 N 0.68136(11) 0.3309(2) 0.2006(8) 0.0416(7) Uani 1 1 d . . . . .
N6 N 0.51290(11) 0.2405(3) -0.3259(10) 0.0556(10) Uani 1 1 d . . . . .
H6 H 0.481249 0.237343 -0.392757 0.067 Uiso 1 1 calc R U . . .
C1 C 0.90769(16) 0.4124(3) 0.6246(13) 0.0571(12) Uani 1 1 d . . . . .
C2 C 0.85063(14) 0.4222(3) 0.6186(11) 0.0446(9) Uani 1 1 d . . . . .
C3 C 0.77895(16) 0.5056(3) 0.7942(11) 0.0492(9) Uani 1 1 d . . . . .
H3A H 0.763951 0.554758 0.920335 0.059 Uiso 1 1 calc R U . . .
C4 C 0.74601(15) 0.4489(3) 0.6122(10) 0.0452(9) Uani 1 1 d . . . . .
H4 H 0.709973 0.460767 0.614514 0.054 Uiso 1 1 calc R U . . .
C5 C 0.76734(12) 0.3734(2) 0.4244(11) 0.0387(7) Uani 1 1 d . . . . .
C6 C 0.82172(13) 0.3595(3) 0.4286(12) 0.0429(8) Uani 1 1 d . . . . .
H6A H 0.837905 0.309993 0.308414 0.052 Uiso 1 1 calc R U . . .
C7 C 0.73284(12) 0.3145(3) 0.2273(9) 0.0383(8) Uani 1 1 d . . . . .
C8 C 0.66717(12) 0.2619(3) -0.0134(9) 0.0369(8) Uani 1 1 d . . . . .
C9 C 0.61308(12) 0.2525(3) -0.1224(10) 0.0392(9) Uani 1 1 d . . . . .
C10 C 0.59866(13) 0.1739(3) -0.3180(11) 0.0470(9) Uani 1 1 d . . . . .
H10 H 0.623103 0.124894 -0.380523 0.056 Uiso 1 1 calc R U . . .
C11 C 0.54737(15) 0.1698(3) -0.4180(11) 0.0542(11) Uani 1 1 d . . . . .
H11 H 0.536937 0.117830 -0.549403 0.065 Uiso 1 1 calc R U . . .
C12 C 0.52516(15) 0.3161(3) -0.1348(13) 0.0586(12) Uani 1 1 d . . . . .
H12 H 0.499659 0.363273 -0.074330 0.070 Uiso 1 1 calc R U . . .
C13 C 0.57577(13) 0.3240(3) -0.0270(11) 0.0499(11) Uani 1 1 d . . . . .
H13 H 0.584787 0.376236 0.107016 0.060 Uiso 1 1 calc R U . . .
S1 S 0.38792(3) 0.37541(6) -0.5794(3) 0.0394(2) Uani 1 1 d . . . . .
O1 O 0.3864(2) 0.4626(3) -0.3436(10) 0.0927(15) Uani 1 1 d . . . . .
H1 H 0.377952 0.438340 -0.180813 0.139 Uiso 1 1 calc R U . . .
O2 O 0.33521(11) 0.3608(3) -0.6761(12) 0.0772(14) Uani 1 1 d . . . . .
O3 O 0.42014(11) 0.4184(3) -0.8145(9) 0.0684(10) Uani 1 1 d . . . . .
O4 O 0.40995(11) 0.2836(2) -0.4406(9) 0.0606(9) Uani 1 1 d . . . . .


_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
N1 C1 1.129(5) . ?
N2 C2 1.331(6) . ?
N2 C3 1.336(5) . ?
N3 H3 0.8600 . ?
N3 N4 1.350(4) . ?
N3 C7 1.346(5) . ?
N4 C8 1.334(4) . ?
N5 C7 1.332(4) . ?
N5 C8 1.356(5) . ?
N6 H6 0.8600 . ?
N6 C11 1.331(6) . ?
N6 C12 1.332(6) . ?
C1 C2 1.458(5) . ?
C2 C6 1.384(6) . ?
C3 H3A 0.9300 . ?
C3 C4 1.378(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(6) . ?
C5 C6 1.396(4) . ?
C5 C7 1.457(5) . ?
C6 H6A 0.9300 . ?
C8 C9 1.465(4) . ?
C9 C10 1.388(6) . ?
C9 C13 1.390(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.379(5) . ?
C13 H13 0.9300 . ?
S1 O1 1.542(4) . ?
S1 O2 1.422(3) . ?
S1 O3 1.443(3) . ?
S1 O4 1.450(3) . ?
O1 H1 0.8200 . ?

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
C2 N2 C3 115.7(4) . . ?
N4 N3 H3 124.8 . . ?
C7 N3 H3 124.8 . . ?
C7 N3 N4 110.5(3) . . ?
C8 N4 N3 102.1(3) . . ?
C7 N5 C8 102.7(3) . . ?
C11 N6 H6 118.5 . . ?
C11 N6 C12 123.0(3) . . ?
C12 N6 H6 118.5 . . ?
N1 C1 C2 178.3(5) . . ?
N2 C2 C1 114.9(4) . . ?
N2 C2 C6 125.8(4) . . ?
C6 C2 C1 119.4(4) . . ?
N2 C3 H3A 118.0 . . ?
N2 C3 C4 124.0(4) . . ?
C4 C3 H3A 118.0 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 C7 119.5(3) . . ?
C6 C5 C7 122.6(4) . . ?
C2 C6 C5 117.4(4) . . ?
C2 C6 H6A 121.3 . . ?
C5 C6 H6A 121.3 . . ?
N3 C7 C5 125.9(3) . . ?
N5 C7 N3 109.7(3) . . ?
N5 C7 C5 124.3(3) . . ?
N4 C8 N5 115.0(3) . . ?
N4 C8 C9 122.4(3) . . ?
N5 C8 C9 122.6(3) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 C13 119.8(3) . . ?
C13 C9 C8 119.0(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.8(4) . . ?
C11 C10 H10 120.6 . . ?
N6 C11 C10 119.8(4) . . ?
N6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N6 C12 H12 120.1 . . ?
N6 C12 C13 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C9 C13 H13 120.6 . . ?
C12 C13 C9 118.8(4) . . ?
C12 C13 H13 120.6 . . ?
O2 S1 O1 106.3(3) . . ?
O2 S1 O3 111.5(2) . . ?
O2 S1 O4 112.75(19) . . ?
O3 S1 O1 103.4(2) . . ?
O3 S1 O4 113.9(2) . . ?
O4 S1 O1 108.3(2) . . ?
S1 O1 H1 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C6 C5 0.5(7) . . . . ?
N2 C3 C4 C5 1.1(6) . . . . ?
N3 N4 C8 N5 -0.4(4) . . . . ?
N3 N4 C8 C9 179.2(3) . . . . ?
N4 N3 C7 N5 0.2(4) . . . . ?
N4 N3 C7 C5 -177.6(3) . . . . ?
N4 C8 C9 C10 7.4(6) . . . . ?
N4 C8 C9 C13 -172.7(4) . . . . ?
N5 C8 C9 C10 -173.1(4) . . . . ?
N5 C8 C9 C13 6.9(6) . . . . ?
N6 C12 C13 C9 0.2(7) . . . . ?
C1 C2 C6 C5 -178.3(4) . . . . ?
C2 N2 C3 C4 -0.9(6) . . . . ?
C3 N2 C2 C1 178.9(4) . . . . ?
C3 N2 C2 C6 0.0(6) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C3 C4 C5 C7 -178.8(4) . . . . ?
C4 C5 C6 C2 -0.3(6) . . . . ?
C4 C5 C7 N3 -179.0(4) . . . . ?
C4 C5 C7 N5 3.5(6) . . . . ?
C6 C5 C7 N3 2.8(6) . . . . ?
C6 C5 C7 N5 -174.7(4) . . . . ?
C7 N3 N4 C8 0.1(4) . . . . ?
C7 N5 C8 N4 0.5(4) . . . . ?
C7 N5 C8 C9 -179.1(3) . . . . ?
C7 C5 C6 C2 178.0(4) . . . . ?
C8 N5 C7 N3 -0.4(4) . . . . ?
C8 N5 C7 C5 177.4(3) . . . . ?
C8 C9 C10 C11 -178.8(4) . . . . ?
C8 C9 C13 C12 178.8(4) . . . . ?
C9 C10 C11 N6 -0.1(6) . . . . ?
C10 C9 C13 C12 -1.3(6) . . . . ?
C11 N6 C12 C13 0.9(7) . . . . ?
C12 N6 C11 C10 -1.0(7) . . . . ?
C13 C9 C10 C11 1.2(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 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.556
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methyl alcohol'
####################################################################### 
# 
# 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_150k
_database_code_depnum_ccdc_archive 'CCDC 2405194'
loop_
_audit_author_name
_audit_author_address
'Jiangying Li'
;Suzhou Institute of NanoTech and NanoBionics
China
;
_audit_update_record             
;
2024-11-25 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'FYX I'
_chemical_formula_moiety         'C13 H8 N6'
_chemical_formula_sum            'C13 H8 N6'
_chemical_formula_weight         248.25
_chemical_absolute_configuration ?
_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 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8498(12)
_cell_length_b                   12.368(3)
_cell_length_c                   12.116(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.377(13)
_cell_angle_gamma                90
_cell_volume                     573.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2114
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      54.938
_cell_measurement_theta_min      3.196
_shelx_estimated_absorpt_T_max   0.791
_shelx_estimated_absorpt_T_min   0.791
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 1
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3748
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.954
_diffrn_reflns_theta_min         3.109
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.594
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.633
_reflns_number_gt                1499
_reflns_number_total             1771
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.391
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(7)
_refine_ls_extinction_coef       0.033(10)
_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   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1771
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      1.149
_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)+(0.0889P)²+0.3866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1979
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9960(19)
 0.0040(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C9(H6), C10(H7), C12(H8), C4(H3), C5(H4), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
N4 N 0.3561(13) 0.5045(5) 0.7208(4) 0.0392(13) Uani 1 1 d . . . . .
C6 C 0.5442(16) 0.4996(5) 0.8196(5) 0.0378(14) Uani 1 1 d . . . . .
N2 N 0.5397(14) 0.3968(5) 0.8608(5) 0.0423(14) Uani 1 1 d . . . . .
H5 H 0.65(2) 0.373(6) 0.933(7) 0.051 Uiso 1 1 d . U . . .
N3 N 0.3490(15) 0.3318(4) 0.7864(5) 0.0431(15) Uani 1 1 d . . . . .
C7 C 0.2369(17) 0.4016(5) 0.7055(5) 0.0395(15) Uani 1 1 d . . . . .
C9 C -0.0834(19) 0.2576(6) 0.5905(6) 0.0482(18) Uani 1 1 d . . . . .
H6 H -0.015149 0.205075 0.645934 0.058 Uiso 1 1 calc R U . . .
C10 C -0.2819(19) 0.2281(6) 0.4935(6) 0.0496(19) Uani 1 1 d . . . . .
H7 H -0.339962 0.153825 0.483924 0.060 Uiso 1 1 calc R U . . .
N5 N -0.3981(17) 0.2954(5) 0.4126(5) 0.0518(16) Uani 1 1 d . . . . .
C11 C -0.3036(18) 0.4011(6) 0.4305(6) 0.0455(17) Uani 1 1 d . . . . .
C12 C -0.1066(17) 0.4385(6) 0.5245(5) 0.0424(16) Uani 1 1 d . . . . .
H8 H -0.055421 0.513313 0.533095 0.051 Uiso 1 1 calc R U . . .
C8 C 0.0162(17) 0.3652(6) 0.6066(6) 0.0408(16) Uani 1 1 d . . . . .
C4 C 0.7698(18) 0.6863(5) 0.8218(6) 0.0441(16) Uani 1 1 d . . . . .
H3 H 0.675534 0.693869 0.746313 0.053 Uiso 1 1 calc R U . . .
C5 C 0.945(2) 0.7716(6) 0.8777(6) 0.0479(18) Uani 1 1 d . . . . .
H4 H 0.970281 0.837083 0.838406 0.057 Uiso 1 1 calc R U . . .
N1 N 1.0820(15) 0.7663(5) 0.9842(5) 0.0441(14) Uani 1 1 d . . . . .
C1 C 1.0455(19) 0.6725(6) 1.0383(6) 0.0464(17) Uani 1 1 d . . . . .
H1 H 1.139333 0.667132 1.113960 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8757(18) 0.5833(6) 0.9874(6) 0.0434(16) Uani 1 1 d . . . . .
H2 H 0.857597 0.518276 1.028072 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7341(16) 0.5893(6) 0.8784(6) 0.0399(15) Uani 1 1 d . . . . .
N6 N -0.547(3) 0.5313(7) 0.2718(7) 0.089(3) Uani 1 1 d . . . . .
C00J C -0.439(2) 0.4730(7) 0.3426(7) 0.063(2) Uani 1 1 d . . . . .


_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
N4 C6 1.330(8) . ?
N4 C7 1.359(9) . ?
C6 N2 1.367(9) . ?
C6 C3 1.469(9) . ?
N2 H5 0.98(8) . ?
N2 N3 1.360(8) . ?
N3 C7 1.341(8) . ?
C7 C8 1.461(9) . ?
C9 H6 0.9500 . ?
C9 C10 1.378(10) . ?
C9 C8 1.392(10) . ?
C10 H7 0.9500 . ?
C10 N5 1.325(10) . ?
N5 C11 1.367(10) . ?
C11 C12 1.376(9) . ?
C11 C00J 1.440(11) . ?
C12 H8 0.9500 . ?
C12 C8 1.389(10) . ?
C4 H3 0.9500 . ?
C4 C5 1.388(10) . ?
C4 C3 1.397(10) . ?
C5 H4 0.9500 . ?
C5 N1 1.340(9) . ?
N1 C1 1.346(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(9) . ?
N6 C00J 1.161(11) . ?

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
C6 N4 C7 102.8(5) . . ?
N4 C6 N2 110.1(5) . . ?
N4 C6 C3 126.4(6) . . ?
N2 C6 C3 123.5(6) . . ?
C6 N2 H5 126(5) . . ?
N3 N2 C6 109.6(5) . . ?
N3 N2 H5 124(5) . . ?
C7 N3 N2 102.2(5) . . ?
N4 C7 C8 123.9(6) . . ?
N3 C7 N4 115.2(6) . . ?
N3 C7 C8 120.8(6) . . ?
C10 C9 H6 120.3 . . ?
C10 C9 C8 119.3(7) . . ?
C8 C9 H6 120.3 . . ?
C9 C10 H7 117.5 . . ?
N5 C10 C9 125.1(7) . . ?
N5 C10 H7 117.5 . . ?
C10 N5 C11 114.9(6) . . ?
N5 C11 C12 124.3(7) . . ?
N5 C11 C00J 113.9(6) . . ?
C12 C11 C00J 121.7(7) . . ?
C11 C12 H8 120.5 . . ?
C11 C12 C8 119.1(7) . . ?
C8 C12 H8 120.5 . . ?
C9 C8 C7 122.3(6) . . ?
C12 C8 C7 120.5(6) . . ?
C12 C8 C9 117.2(6) . . ?
C5 C4 H3 120.6 . . ?
C5 C4 C3 118.8(6) . . ?
C3 C4 H3 120.6 . . ?
C4 C5 H4 118.3 . . ?
N1 C5 C4 123.4(7) . . ?
N1 C5 H4 118.3 . . ?
C5 N1 C1 117.4(6) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.5(6) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(7) . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C6 118.8(6) . . ?
C2 C3 C6 123.3(6) . . ?
C2 C3 C4 117.9(6) . . ?
N6 C00J C11 179.6(10) . . ?

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
N4 C6 N2 N3 1.1(8) . . . . ?
N4 C6 C3 C4 -10.1(10) . . . . ?
N4 C6 C3 C2 169.0(6) . . . . ?
N4 C7 C8 C9 175.9(7) . . . . ?
N4 C7 C8 C12 -4.8(10) . . . . ?
C6 N4 C7 N3 -2.4(8) . . . . ?
C6 N4 C7 C8 -179.5(6) . . . . ?
C6 N2 N3 C7 -2.4(7) . . . . ?
N2 C6 C3 C4 169.6(6) . . . . ?
N2 C6 C3 C2 -11.3(10) . . . . ?
N2 N3 C7 N4 3.0(8) . . . . ?
N2 N3 C7 C8 -179.8(6) . . . . ?
N3 C7 C8 C9 -1.0(10) . . . . ?
N3 C7 C8 C12 178.3(7) . . . . ?
C7 N4 C6 N2 0.7(7) . . . . ?
C7 N4 C6 C3 -179.6(6) . . . . ?
C9 C10 N5 C11 0.7(11) . . . . ?
C10 C9 C8 C7 -177.8(7) . . . . ?
C10 C9 C8 C12 3.0(10) . . . . ?
C10 N5 C11 C12 -0.7(11) . . . . ?
C10 N5 C11 C00J -178.7(8) . . . . ?
N5 C11 C12 C8 2.0(10) . . . . ?
C11 C12 C8 C7 177.7(6) . . . . ?
C11 C12 C8 C9 -3.0(9) . . . . ?
C8 C9 C10 N5 -1.9(12) . . . . ?
C4 C5 N1 C1 0.3(11) . . . . ?
C5 C4 C3 C6 179.2(6) . . . . ?
C5 C4 C3 C2 0.1(10) . . . . ?
C5 N1 C1 C2 0.3(11) . . . . ?
N1 C1 C2 C3 -0.7(11) . . . . ?
C1 C2 C3 C6 -178.6(6) . . . . ?
C1 C2 C3 C4 0.5(10) . . . . ?
C3 C6 N2 N3 -178.6(6) . . . . ?
C3 C4 C5 N1 -0.5(12) . . . . ?
C00J C11 C12 C8 179.8(7) . . . . ?


_olex2_exptl_crystal_mounting_method 1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9960(19)
2 0.0040(19)

_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2402735'
loop_
_audit_author_name
_audit_author_address
'Jiangying Li'
;Suzhou Institute of Nano Tech and Nano Bionics
China
;
_audit_update_record             
;
2024-11-14 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'FYX-H2SO4 II'
_chemical_formula_moiety         'H O4 S, C13 H9 N6'
_chemical_formula_sum            'C13 H10 N6 O4 S'
_chemical_formula_weight         346.33
_chemical_absolute_configuration ?
_chemical_melting_point          507.55
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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           34
_space_group_name_H-M_alt        'P n n 2'
_space_group_name_Hall           'P 2 -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.6047(13)
_cell_length_b                   25.471(3)
_cell_length_c                   4.4874(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1440.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.127
_cell_measurement_theta_min      4.295
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.520
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1681 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.7125.
The λ/2 correction factor is Not present.
;
_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    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15054
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.093
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                2613
_reflns_number_total             2754
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.232
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 966 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.059
_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)+(0.0454P)²+0.4682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0896
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H6), N1(H1), C12(H9), C9(H7), C10(H8), C4(H4), C2(H3), C5(H5), C1(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.87928(5) 0.11341(2) 0.77432(19) 0.02073(19) Uani 1 1 d . . . . .
O2 O 0.91979(18) 0.08014(7) 1.0120(5) 0.0303(5) Uani 1 1 d . . . . .
O1 O 0.86537(16) 0.16695(7) 0.8728(6) 0.0327(6) Uani 1 1 d . . . . .
O3 O 0.78569(16) 0.09199(7) 0.6296(6) 0.0295(5) Uani 1 1 d . . . . .
N3 N 0.76756(17) 0.25465(8) 0.6558(6) 0.0207(5) Uani 1 1 d . . . . .
H6 H 0.790914 0.222262 0.674661 0.025 Uiso 1 1 calc R U . . .
N4 N 0.67501(18) 0.32134(8) 0.4899(6) 0.0223(5) Uani 1 1 d . . . . .
N2 N 0.80273(17) 0.29594(8) 0.8151(6) 0.0225(5) Uani 1 1 d . . . . .
N5 N 0.50901(18) 0.17229(9) -0.1174(6) 0.0261(5) Uani 1 1 d . . . . .
N1 N 0.7654(2) 0.48941(8) 1.0270(6) 0.0281(6) Uani 1 1 d . . . . .
H1 H 0.768197 0.521608 1.097644 0.034 Uiso 1 1 calc R U . . .
O4 O 0.96872(18) 0.11429(10) 0.5378(6) 0.0370(6) Uani 1 1 d . . . . .
C6 C 0.7443(2) 0.33509(9) 0.7072(7) 0.0204(6) Uani 1 1 d . . . . .
C8 C 0.6315(2) 0.23552(9) 0.2638(8) 0.0201(5) Uani 1 1 d . . . . .
C12 C 0.6444(2) 0.18124(10) 0.2628(8) 0.0230(6) Uani 1 1 d . . . . .
H9 H 0.694808 0.164646 0.388854 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5566(2) 0.25745(10) 0.0725(7) 0.0241(6) Uani 1 1 d . . . . .
H7 H 0.545091 0.294310 0.070064 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6914(2) 0.27000(10) 0.4634(7) 0.0204(6) Uani 1 1 d . . . . .
C3 C 0.7538(2) 0.38931(9) 0.8173(7) 0.0210(6) Uani 1 1 d . . . . .
N6 N 0.5924(2) 0.05048(10) 0.0606(8) 0.0401(7) Uani 1 1 d . . . . .
C10 C 0.4987(2) 0.22451(12) -0.1157(7) 0.0257(6) Uani 1 1 d . . . . .
H8 H 0.449371 0.240023 -0.249425 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6823(2) 0.42714(10) 0.7194(8) 0.0272(7) Uani 1 1 d . . . . .
H4 H 0.628837 0.418315 0.578702 0.033 Uiso 1 1 calc R U . . .
C2 C 0.8325(2) 0.40331(10) 1.0203(7) 0.0252(6) Uani 1 1 d . . . . .
H3 H 0.882546 0.378058 1.087556 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5810(2) 0.15226(10) 0.0715(7) 0.0240(6) Uani 1 1 d . . . . .
C5 C 0.6897(2) 0.47738(11) 0.8282(8) 0.0301(7) Uani 1 1 d . . . . .
H5 H 0.641370 0.503571 0.762775 0.036 Uiso 1 1 calc R U . . .
C1 C 0.8368(2) 0.45429(11) 1.1219(8) 0.0284(7) Uani 1 1 d . . . . .
H2 H 0.890312 0.464513 1.259218 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5888(2) 0.09525(11) 0.0680(8) 0.0294(7) Uani 1 1 d . . . . .
H10 H 0.954(4) 0.099(2) 0.359(15) 0.082(17) Uiso 1 1 d . . . . .


_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 O2 1.455(2) . ?
S1 O1 1.444(2) . ?
S1 O3 1.453(2) . ?
S1 O4 1.549(2) . ?
N3 H6 0.8800 . ?
N3 N2 1.347(3) . ?
N3 C7 1.349(4) . ?
N4 C6 1.355(4) . ?
N4 C7 1.329(3) . ?
N2 C6 1.331(3) . ?
N5 C10 1.336(4) . ?
N5 C11 1.342(4) . ?
N1 H1 0.8800 . ?
N1 C5 1.342(4) . ?
N1 C1 1.338(4) . ?
O4 H10 0.91(6) . ?
C6 C3 1.471(3) . ?
C8 C12 1.392(3) . ?
C8 C9 1.393(4) . ?
C8 C7 1.464(4) . ?
C12 H9 0.9500 . ?
C12 C11 1.386(4) . ?
C9 H7 0.9500 . ?
C9 C10 1.397(4) . ?
C3 C4 1.391(4) . ?
C3 C2 1.394(4) . ?
N6 C13 1.142(4) . ?
C10 H8 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.373(4) . ?
C2 H3 0.9500 . ?
C2 C1 1.377(4) . ?
C11 C13 1.455(4) . ?
C5 H5 0.9500 . ?
C1 H2 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
O2 S1 O4 104.80(14) . . ?
O1 S1 O2 111.61(14) . . ?
O1 S1 O3 113.12(12) . . ?
O1 S1 O4 106.52(13) . . ?
O3 S1 O2 113.21(13) . . ?
O3 S1 O4 106.87(14) . . ?
N2 N3 H6 124.8 . . ?
N2 N3 C7 110.3(2) . . ?
C7 N3 H6 124.8 . . ?
C7 N4 C6 102.6(2) . . ?
C6 N2 N3 102.1(2) . . ?
C10 N5 C11 116.1(2) . . ?
C5 N1 H1 118.8 . . ?
C1 N1 H1 118.8 . . ?
C1 N1 C5 122.5(3) . . ?
S1 O4 H10 117(3) . . ?
N4 C6 C3 122.4(2) . . ?
N2 C6 N4 115.1(2) . . ?
N2 C6 C3 122.4(3) . . ?
C12 C8 C9 118.4(3) . . ?
C12 C8 C7 122.5(3) . . ?
C9 C8 C7 119.1(2) . . ?
C8 C12 H9 121.2 . . ?
C11 C12 C8 117.7(3) . . ?
C11 C12 H9 121.2 . . ?
C8 C9 H7 120.5 . . ?
C8 C9 C10 119.1(3) . . ?
C10 C9 H7 120.5 . . ?
N3 C7 C8 125.8(2) . . ?
N4 C7 N3 109.8(2) . . ?
N4 C7 C8 124.4(3) . . ?
C4 C3 C6 119.5(3) . . ?
C4 C3 C2 119.4(2) . . ?
C2 C3 C6 121.1(2) . . ?
N5 C10 C9 123.4(3) . . ?
N5 C10 H8 118.3 . . ?
C9 C10 H8 118.3 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C2 H3 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H3 120.5 . . ?
N5 C11 C12 125.3(3) . . ?
N5 C11 C13 114.7(3) . . ?
C12 C11 C13 120.0(3) . . ?
N1 C5 C4 119.9(3) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C1 C2 119.9(3) . . ?
N1 C1 H2 120.1 . . ?
C2 C1 H2 120.1 . . ?
N6 C13 C11 178.1(4) . . ?

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
_geom_hbond_publ_flag
N3 H6 O1 0.88 1.91 2.731(3) 154.1 . yes
N1 H1 O3 0.88 1.92 2.730(3) 151.9 4_655 yes
O4 H10 O2 0.91(6) 1.69(7) 2.589(3) 172(5) 1_554 yes

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
N3 N2 C6 N4 -0.3(3) . . . . ?
N3 N2 C6 C3 179.3(2) . . . . ?
N4 C6 C3 C4 6.8(4) . . . . ?
N4 C6 C3 C2 -173.8(3) . . . . ?
N2 N3 C7 N4 0.3(3) . . . . ?
N2 N3 C7 C8 -177.1(2) . . . . ?
N2 C6 C3 C4 -172.7(3) . . . . ?
N2 C6 C3 C2 6.6(4) . . . . ?
C6 N4 C7 N3 -0.4(3) . . . . ?
C6 N4 C7 C8 177.0(3) . . . . ?
C6 C3 C4 C5 178.4(3) . . . . ?
C6 C3 C2 C1 -178.6(3) . . . . ?
C8 C12 C11 N5 1.1(5) . . . . ?
C8 C12 C11 C13 -178.1(3) . . . . ?
C8 C9 C10 N5 1.9(4) . . . . ?
C12 C8 C9 C10 -1.0(4) . . . . ?
C12 C8 C7 N3 3.1(5) . . . . ?
C12 C8 C7 N4 -173.8(3) . . . . ?
C9 C8 C12 C11 -0.3(4) . . . . ?
C9 C8 C7 N3 -178.7(3) . . . . ?
C9 C8 C7 N4 4.4(4) . . . . ?
C7 N3 N2 C6 0.0(3) . . . . ?
C7 N4 C6 N2 0.4(3) . . . . ?
C7 N4 C6 C3 -179.2(3) . . . . ?
C7 C8 C12 C11 177.9(3) . . . . ?
C7 C8 C9 C10 -179.3(3) . . . . ?
C3 C4 C5 N1 -0.1(5) . . . . ?
C3 C2 C1 N1 0.5(4) . . . . ?
C10 N5 C11 C12 -0.3(4) . . . . ?
C10 N5 C11 C13 178.9(3) . . . . ?
C4 C3 C2 C1 0.8(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C11 N5 C10 C9 -1.2(4) . . . . ?
C5 N1 C1 C2 -1.6(5) . . . . ?
C1 N1 C5 C4 1.4(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methyl alcohol'
####################################################################### 
# 
# 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_b240227b_a
_database_code_depnum_ccdc_archive 'CCDC 2402736'
loop_
_audit_author_name
_audit_author_address
'Jiangying Li'
;Suzhou Institute of Nano Tech and Nano Bionics
China
;
_audit_update_record             
;
2024-11-14 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2024-11-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'FYX-H2SO4 I'
_chemical_formula_moiety         'H O4 S, C13 H9 N6'
_chemical_formula_sum            'C13 H10 N6 O4 S'
_chemical_formula_weight         346.33
_chemical_melting_point          503.95
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.6846(3)
_cell_length_b                   17.1907(5)
_cell_length_c                   9.6432(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3710(10)
_cell_angle_gamma                90
_cell_volume                     1438.44(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      27.489
_cell_measurement_theta_min      2.369
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9033.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_preparation       1
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methyl alcohol'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.993
_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       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            26603
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         2.423
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          1
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2144
_reflns_number_total             2529
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.446
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.010(4)
_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   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.165
_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)+(0.0239P)²+1.9345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          1
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H6), N1(H1), C12(H9), C4(H4), C2(H3), C9(H7), C5(H5), C1(H2), C10(H8)
2.b Tetrahedral OH refined with riding coordinates:
 O4(H10)
;
_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 0.39592(7) 0.86946(3) 0.80817(6) 0.0292(2) Uani 1 1 d . . . . .
N4 N 0.4864(2) 0.51474(11) 0.25991(19) 0.0279(5) Uani 1 1 d . . . . .
N3 N 0.3266(2) 0.43960(11) 0.3670(2) 0.0308(5) Uani 1 1 d . . . . .
H6 H 0.257144 0.425198 0.424228 0.037 Uiso 1 1 calc R U . . .
N2 N 0.3937(2) 0.39219(12) 0.2761(2) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.7853(2) 0.36861(12) -0.0927(2) 0.0327(5) Uani 1 1 d . . . . .
H1 H 0.847425 0.353810 -0.156116 0.039 Uiso 1 1 calc R U . . .
N5 N 0.2606(2) 0.71162(12) 0.5890(2) 0.0348(5) Uani 1 1 d . . . . .
C8 C 0.3365(3) 0.57942(14) 0.4382(2) 0.0265(5) Uani 1 1 d . . . . .
C7 C 0.3820(3) 0.51215(13) 0.3570(2) 0.0256(5) Uani 1 1 d . . . . .
C11 C 0.1911(3) 0.64276(14) 0.6078(2) 0.0288(5) Uani 1 1 d . . . . .
N6 N -0.0108(3) 0.64129(16) 0.7983(3) 0.0497(6) Uani 1 1 d . . . . .
C12 C 0.2241(3) 0.57573(14) 0.5365(2) 0.0284(5) Uani 1 1 d . . . . .
H9 H 0.172297 0.528954 0.553940 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6959(3) 0.46679(14) 0.0524(2) 0.0299(5) Uani 1 1 d . . . . .
H4 H 0.700703 0.518327 0.084868 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4886(3) 0.44006(14) 0.2146(2) 0.0266(5) Uani 1 1 d . . . . .
C3 C 0.5902(3) 0.41474(14) 0.1047(2) 0.0266(5) Uani 1 1 d . . . . .
C2 C 0.5852(3) 0.33883(15) 0.0549(3) 0.0339(6) Uani 1 1 d . . . . .
H3 H 0.514261 0.302955 0.088910 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4088(3) 0.65031(15) 0.4166(3) 0.0343(6) Uani 1 1 d . . . . .
H7 H 0.485117 0.654747 0.350684 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7930(3) 0.44203(15) -0.0469(2) 0.0332(6) Uani 1 1 d . . . . .
H5 H 0.865004 0.476633 -0.082853 0.040 Uiso 1 1 calc R U . . .
C1 C 0.6848(3) 0.31711(15) -0.0442(3) 0.0352(6) Uani 1 1 d . . . . .
H2 H 0.682905 0.265889 -0.078323 0.042 Uiso 1 1 calc R U . . .
C13 C 0.0768(3) 0.64207(15) 0.7126(3) 0.0352(6) Uani 1 1 d . . . . .
C10 C 0.3670(3) 0.71392(15) 0.4933(3) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.416158 0.761602 0.477323 0.047 Uiso 1 1 calc R U . . .
O1 O 0.51641(19) 0.81386(10) 0.77616(17) 0.0334(4) Uani 1 1 d . . . . .
O3 O 0.3545(2) 0.86392(12) 0.95096(19) 0.0472(5) Uani 1 1 d . . . . .
O2 O 0.4317(2) 0.94736(10) 0.7670(2) 0.0461(5) Uani 1 1 d . . . . .
O4 O 0.2505(2) 0.84687(13) 0.7180(2) 0.0585(6) Uani 1 1 d . . . . .
H10 H 0.236743 0.799180 0.722517 0.088 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 O1 1.4596(17) . ?
S1 O3 1.4406(18) . ?
S1 O2 1.4345(19) . ?
S1 O4 1.553(2) . ?
N4 C7 1.330(3) . ?
N4 C6 1.357(3) . ?
N3 H6 0.8700 . ?
N3 N2 1.348(3) . ?
N3 C7 1.342(3) . ?
N2 C6 1.322(3) . ?
N1 H1 0.8700 . ?
N1 C5 1.338(3) . ?
N1 C1 1.341(3) . ?
N5 C11 1.344(3) . ?
N5 C10 1.333(3) . ?
C8 C7 1.460(3) . ?
C8 C12 1.390(3) . ?
C8 C9 1.391(3) . ?
C11 C12 1.378(3) . ?
C11 C13 1.446(3) . ?
N6 C13 1.146(3) . ?
C12 H9 0.9400 . ?
C4 H4 0.9400 . ?
C4 C3 1.391(3) . ?
C4 C5 1.369(3) . ?
C6 C3 1.472(3) . ?
C3 C2 1.390(3) . ?
C2 H3 0.9400 . ?
C2 C1 1.367(3) . ?
C9 H7 0.9400 . ?
C9 C10 1.378(4) . ?
C5 H5 0.9400 . ?
C1 H2 0.9400 . ?
C10 H8 0.9400 . ?
O4 H10 0.8300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O4 106.93(11) . . ?
O3 S1 O1 111.61(11) . . ?
O3 S1 O4 106.83(13) . . ?
O2 S1 O1 112.78(11) . . ?
O2 S1 O3 113.07(12) . . ?
O2 S1 O4 105.01(13) . . ?
C7 N4 C6 102.38(19) . . ?
N2 N3 H6 124.8 . . ?
C7 N3 H6 124.8 . . ?
C7 N3 N2 110.43(19) . . ?
C6 N2 N3 102.12(19) . . ?
C5 N1 H1 118.9 . . ?
C5 N1 C1 122.1(2) . . ?
C1 N1 H1 118.9 . . ?
C10 N5 C11 116.6(2) . . ?
C12 C8 C7 122.9(2) . . ?
C12 C8 C9 118.4(2) . . ?
C9 C8 C7 118.7(2) . . ?
N4 C7 N3 109.8(2) . . ?
N4 C7 C8 123.9(2) . . ?
N3 C7 C8 126.3(2) . . ?
N5 C11 C12 124.4(2) . . ?
N5 C11 C13 115.2(2) . . ?
C12 C11 C13 120.3(2) . . ?
C8 C12 H9 121.0 . . ?
C11 C12 C8 117.9(2) . . ?
C11 C12 H9 121.0 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
N4 C6 C3 121.9(2) . . ?
N2 C6 N4 115.3(2) . . ?
N2 C6 C3 122.8(2) . . ?
C4 C3 C6 119.6(2) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 C6 121.0(2) . . ?
C3 C2 H3 120.5 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H3 120.5 . . ?
C8 C9 H7 120.5 . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H7 120.5 . . ?
N1 C5 C4 120.0(2) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C1 C2 120.2(2) . . ?
N1 C1 H2 119.9 . . ?
C2 C1 H2 119.9 . . ?
N6 C13 C11 178.2(3) . . ?
N5 C10 C9 123.6(2) . . ?
N5 C10 H8 118.2 . . ?
C9 C10 H8 118.2 . . ?
S1 O4 H10 109.5 . . ?

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
_geom_hbond_publ_flag
N3 H6 O3 0.87 1.90 2.734(3) 161.2 2_546 yes
N1 H1 O1 0.87 1.82 2.689(2) 173.6 2_645 yes
O4 H10 N5 0.83 2.00 2.640(3) 133.7 . yes

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
N4 C6 C3 C4 5.1(3) . . . . ?
N4 C6 C3 C2 -176.8(2) . . . . ?
N3 N2 C6 N4 -0.1(3) . . . . ?
N3 N2 C6 C3 179.8(2) . . . . ?
N2 N3 C7 N4 0.0(3) . . . . ?
N2 N3 C7 C8 179.7(2) . . . . ?
N2 C6 C3 C4 -174.9(2) . . . . ?
N2 C6 C3 C2 3.3(4) . . . . ?
N5 C11 C12 C8 -0.3(4) . . . . ?
C8 C9 C10 N5 0.5(4) . . . . ?
C7 N4 C6 N2 0.1(3) . . . . ?
C7 N4 C6 C3 -179.8(2) . . . . ?
C7 N3 N2 C6 0.1(3) . . . . ?
C7 C8 C12 C11 179.6(2) . . . . ?
C7 C8 C9 C10 -179.7(2) . . . . ?
C11 N5 C10 C9 -0.9(4) . . . . ?
C12 C8 C7 N4 178.3(2) . . . . ?
C12 C8 C7 N3 -1.4(4) . . . . ?
C12 C8 C9 C10 0.1(4) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C6 N4 C7 N3 -0.1(2) . . . . ?
C6 N4 C7 C8 -179.8(2) . . . . ?
C6 C3 C2 C1 -178.0(2) . . . . ?
C3 C4 C5 N1 0.1(4) . . . . ?
C3 C2 C1 N1 -0.3(4) . . . . ?
C9 C8 C7 N4 -1.9(3) . . . . ?
C9 C8 C7 N3 178.4(2) . . . . ?
C9 C8 C12 C11 -0.2(3) . . . . ?
C5 N1 C1 C2 0.3(4) . . . . ?
C5 C4 C3 C6 178.1(2) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C1 N1 C5 C4 -0.3(4) . . . . ?
C13 C11 C12 C8 -179.1(2) . . . . ?
C10 N5 C11 C12 0.8(4) . . . . ?
C10 N5 C11 C13 179.7(2) . . . . ?


_olex2_exptl_crystal_mounting_method 1
_olex2_submission_original_sample_id 1
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
