# Supplementary Information (SI) for Journal of Materials Chemistry A.
# 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_0117-1
_database_code_depnum_ccdc_archive 'CCDC 2403772'
loop_
_audit_author_name
_audit_author_address
'yingle liu'
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-03-02 downloaded from the CCDC.
;
_audit_creation_date             2024-01-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 N11 O4'
_chemical_formula_sum            'C5 H5 N11 O4'
_chemical_formula_weight         283.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N '
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.61900(10)
_cell_length_b                   10.9594(2)
_cell_length_c                   16.6465(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.089(2)
_cell_angle_gamma                90
_cell_volume                     1012.23(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4258
_cell_measurement_temperature    296.31(10)
_cell_measurement_theta_max      75.9050
_cell_measurement_theta_min      4.8300
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    1.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5556
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         4.850
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.31(10)
_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 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00  73.00   0.50    2.00    --  108.42 -81.00-109.00   52
  2  ω     26.00  52.00   0.50    1.37    --   47.52 -81.00-109.00   52
  3  ω    -71.00 -29.00   0.50    2.00    --  -91.75  61.00 -30.00   84
  4  ω    -47.00 -21.00   0.50    2.00    --  -91.75  45.00 -60.00   52
  5  ω    -51.00 -24.00   0.50    2.00    --  -91.75  61.00-150.00   54
  6  ω    -44.00 -19.00   0.50    2.00    --  -91.75  45.00-180.00   50
  7  ω    -48.00 -22.00   0.50    2.00    --  -91.75  45.00-150.00   52
  8  ω    -48.00 -19.00   0.50    2.00    --  -91.75  45.00   0.00   58
  9  ω    -50.00 -20.00   0.50    2.00    --  -91.75  45.00  30.00   60
 10  ω    -48.00 -21.00   0.50    2.00    --  -91.75  45.00  90.00   54
 11  ω   -160.00 -81.00   0.50    2.00    --  -91.75 -15.00  90.00  158
 12  ω   -113.00 -71.00   0.50    1.37    --  -47.52-125.00  30.00   84
 13  ω    -96.00 -55.00   0.50    1.37    --  -47.52 -81.00-109.00   82
 14  ω    -50.00 -24.00   0.50    1.37    --  -47.52 -81.00-109.00   52
 15  ω   -100.00 -43.00   0.50    2.00    --  -91.75  81.00  13.00  114
 16  ω    -73.00  25.00   0.50    1.37    --  -47.52  81.00  13.00  196
 17  ω     37.00  71.00   0.50    2.00    --  108.42 -61.00 -60.00   68
 18  ω     42.00  67.00   0.50    2.00    --  108.42 -61.00 -90.00   50
 19  ω     41.00  67.00   0.50    2.00    --  108.42 -61.00  60.00   52
 20  ω     41.00  68.00   0.50    2.00    --  108.42 -61.00  90.00   54
 21  ω     91.00 132.00   0.50    2.00    --  108.42  15.00 -30.00   82
 22  ω    140.00 174.00   0.50    2.00    --  108.42  15.00 -30.00   68
 23  ω     83.00 172.00   0.50    2.00    --  108.42  81.00  13.00  178
;
_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      -0.2240894000
_diffrn_orient_matrix_UB_12      -0.0815798000
_diffrn_orient_matrix_UB_13      -0.0023433000
_diffrn_orient_matrix_UB_21      -0.1028600000
_diffrn_orient_matrix_UB_22      0.0892659000
_diffrn_orient_matrix_UB_23      0.0572042000
_diffrn_orient_matrix_UB_31      -0.1275563000
_diffrn_orient_matrix_UB_32      0.0716319000
_diffrn_orient_matrix_UB_33      -0.0742383000
_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                1569
_reflns_number_total             1774
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.409
_refine_ls_extinction_coef       0.018(3)
_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   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.188
_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)+(0.1510P)²+0.6189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2305
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8)
2.b X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N2(H2A,H2B)
;
_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
O1 O 0.4792(4) 0.6755(2) 0.33071(14) 0.0431(7) Uani 1 1 d . . . . .
N8 N 0.5860(4) 0.5294(2) 0.21523(15) 0.0312(7) Uani 1 1 d . . . . .
H8 H 0.468476 0.563543 0.234056 0.037 Uiso 1 1 calc R U . . .
O3 O 0.1674(4) 0.6248(3) 0.18199(15) 0.0480(8) Uani 1 1 d . . . . .
O4 O 0.0421(4) 0.6670(3) 0.05604(16) 0.0507(8) Uani 1 1 d . . . . .
N10 N 0.3640(5) 0.5531(2) 0.08115(16) 0.0367(7) Uani 1 1 d . . . . .
N6 N 1.1184(4) 0.3937(2) 0.31000(15) 0.0294(7) Uani 1 1 d . . . . .
N7 N 0.9203(5) 0.4111(2) 0.25424(15) 0.0310(7) Uani 1 1 d . . . . .
O2 O 0.7900(6) 0.7670(3) 0.39717(19) 0.0683(11) Uani 1 1 d . . . . .
N3 N 1.4019(5) 0.4087(2) 0.41432(17) 0.0373(7) Uani 1 1 d . . . . .
N11 N 0.1897(5) 0.6174(2) 0.10917(16) 0.0360(7) Uani 1 1 d . . . . .
N9 N 0.7035(5) 0.4429(2) 0.09944(16) 0.0388(7) Uani 1 1 d . . . . .
H9A H 0.680492 0.433268 0.047516 0.047 Uiso 1 1 calc R U . . .
H9B H 0.827073 0.410494 0.128784 0.047 Uiso 1 1 calc R U . . .
N5 N 1.2804(5) 0.3054(2) 0.30219(16) 0.0373(7) Uani 1 1 d . . . . .
N4 N 1.4466(5) 0.3157(3) 0.36533(18) 0.0404(8) Uani 1 1 d . . . . .
C5 C 0.5507(5) 0.5069(3) 0.13378(18) 0.0311(7) Uani 1 1 d . . . . .
N2 N 1.1473(5) 0.6221(3) 0.46420(15) 0.0372(7) Uani 1 1 d . . . . .
H2A H 1.070515 0.684426 0.478261 0.045 Uiso 1 1 calc R U . . .
H2B H 1.280695 0.600062 0.493261 0.045 Uiso 1 1 calc R U . . .
N1 N 0.6955(5) 0.6799(3) 0.35735(15) 0.0361(7) Uani 1 1 d . . . . .
C1 C 0.7889(5) 0.5037(3) 0.27121(17) 0.0277(7) Uani 1 1 d . . . . .
C4 C 1.1955(5) 0.4567(3) 0.37822(18) 0.0302(7) Uani 1 1 d . . . . .
C3 C 1.0602(5) 0.5600(3) 0.39784(17) 0.0289(7) Uani 1 1 d . . . . .
C2 C 0.8492(5) 0.5801(3) 0.34274(18) 0.0293(7) 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
O1 N1 1.227(4) . ?
N8 H8 0.8600 . ?
N8 C5 1.361(4) . ?
N8 C1 1.383(4) . ?
O3 N11 1.241(4) . ?
O4 N11 1.239(4) . ?
N10 N11 1.348(4) . ?
N10 C5 1.354(4) . ?
N6 N7 1.346(3) . ?
N6 N5 1.349(4) . ?
N6 C4 1.341(4) . ?
N7 C1 1.311(4) . ?
O2 N1 1.233(4) . ?
N3 N4 1.354(4) . ?
N3 C4 1.327(4) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N9 C5 1.308(4) . ?
N5 N4 1.296(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C3 1.323(4) . ?
N1 C2 1.438(4) . ?
C1 C2 1.452(4) . ?
C4 C3 1.431(4) . ?
C3 C2 1.397(4) . ?

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
C5 N8 H8 116.2 . . ?
C5 N8 C1 127.5(3) . . ?
C1 N8 H8 116.2 . . ?
N11 N10 C5 120.2(3) . . ?
N7 N6 N5 122.2(2) . . ?
C4 N6 N7 129.2(3) . . ?
C4 N6 N5 108.5(2) . . ?
C1 N7 N6 113.2(2) . . ?
C4 N3 N4 104.9(2) . . ?
O3 N11 N10 124.3(3) . . ?
O4 N11 O3 120.6(3) . . ?
O4 N11 N10 115.1(3) . . ?
H9A N9 H9B 120.0 . . ?
C5 N9 H9A 120.0 . . ?
C5 N9 H9B 120.0 . . ?
N4 N5 N6 105.7(2) . . ?
N5 N4 N3 112.0(2) . . ?
N10 C5 N8 123.6(3) . . ?
N9 C5 N8 122.0(3) . . ?
N9 C5 N10 114.4(3) . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
O1 N1 O2 122.8(3) . . ?
O1 N1 C2 119.7(3) . . ?
O2 N1 C2 117.4(3) . . ?
N8 C1 C2 119.7(3) . . ?
N7 C1 N8 116.4(3) . . ?
N7 C1 C2 123.8(3) . . ?
N6 C4 C3 119.2(3) . . ?
N3 C4 N6 108.8(3) . . ?
N3 C4 C3 131.9(3) . . ?
N2 C3 C4 117.2(3) . . ?
N2 C3 C2 129.1(3) . . ?
C2 C3 C4 113.7(3) . . ?
N1 C2 C1 120.6(3) . . ?
C3 C2 N1 118.6(3) . . ?
C3 C2 C1 120.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C1 27.8(4) . . . . ?
O1 N1 C2 C3 -153.6(3) . . . . ?
N8 C1 C2 N1 2.1(4) . . . . ?
N8 C1 C2 C3 -176.5(3) . . . . ?
N6 N7 C1 N8 178.1(2) . . . . ?
N6 N7 C1 C2 -0.1(4) . . . . ?
N6 N5 N4 N3 -0.7(4) . . . . ?
N6 C4 C3 N2 -177.7(3) . . . . ?
N6 C4 C3 C2 2.8(4) . . . . ?
N7 N6 N5 N4 179.3(3) . . . . ?
N7 N6 C4 N3 -179.0(3) . . . . ?
N7 N6 C4 C3 -1.5(5) . . . . ?
N7 C1 C2 N1 -179.8(3) . . . . ?
N7 C1 C2 C3 1.6(4) . . . . ?
O2 N1 C2 C1 -152.5(3) . . . . ?
O2 N1 C2 C3 26.1(4) . . . . ?
N3 C4 C3 N2 -0.9(5) . . . . ?
N3 C4 C3 C2 179.6(3) . . . . ?
N11 N10 C5 N8 -5.4(4) . . . . ?
N11 N10 C5 N9 177.8(3) . . . . ?
N5 N6 N7 C1 -177.9(3) . . . . ?
N5 N6 C4 N3 -0.8(4) . . . . ?
N5 N6 C4 C3 176.7(3) . . . . ?
N4 N3 C4 N6 0.4(3) . . . . ?
N4 N3 C4 C3 -176.7(3) . . . . ?
C5 N8 C1 N7 -28.0(4) . . . . ?
C5 N8 C1 C2 150.2(3) . . . . ?
C5 N10 N11 O3 -10.3(4) . . . . ?
C5 N10 N11 O4 172.3(3) . . . . ?
N2 C3 C2 N1 -0.9(5) . . . . ?
N2 C3 C2 C1 177.7(3) . . . . ?
C1 N8 C5 N10 -168.4(3) . . . . ?
C1 N8 C5 N9 8.1(5) . . . . ?
C4 N6 N7 C1 0.0(4) . . . . ?
C4 N6 N5 N4 0.9(4) . . . . ?
C4 N3 N4 N5 0.2(4) . . . . ?
C4 C3 C2 N1 178.5(3) . . . . ?
C4 C3 C2 C1 -2.9(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.954
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_e
_database_code_depnum_ccdc_archive 'CCDC 2403775'
loop_
_audit_author_name
_audit_author_address
'yingle liu'
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-03-02 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H7 N11'
_chemical_formula_sum            'C4 H7 N11'
_chemical_formula_weight         209.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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'

_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                   6.9603(6)
_cell_length_b                   9.2575(7)
_cell_length_c                   12.6543(12)
_cell_angle_alpha                92.444(7)
_cell_angle_beta                 99.747(8)
_cell_angle_gamma                93.409(7)
_cell_volume                     801.04(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2918
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.4890
_cell_measurement_theta_min      3.5180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5097
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.752
_diffrn_reflns_theta_min         3.549
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -23.00   1.00    1.00    --  -40.73  38.00 -60.00   33
  2  ω    -18.00  32.00   1.00    1.00    --  -40.73  38.00 -60.00   50
  3  ω    -58.00  39.00   1.00    1.00    --  -40.73  19.00-150.00   97
  4  ω     26.00  83.00   1.00    1.00    --   40.73-125.00   0.00   57
  5  ω     31.00 109.00   1.00    1.00    --  107.58 -94.00 -90.00   78
  6  ω     69.00 103.00   1.00    1.00    --  107.58 -94.00-180.00   34
  7  ω     30.00  80.00   1.00    1.00    --   40.73-125.00-180.00   50
  8  ω     35.00  87.00   1.00    1.00    --  107.58 -45.00 -90.00   52
  9  ω     31.00 128.00   1.00    1.00    --  107.58 -30.00 -30.00   97
 10  ω    115.00 141.00   1.00    1.00    --  107.58  77.00-180.00   26
 11  ω    133.00 159.00   1.00    1.00    --  107.58 125.00-180.00   26
 12  ω     94.00 128.00   1.00    1.00    --  107.58 125.00   0.00   34
 13  ω    115.00 167.00   1.00    1.00    --  107.58  77.00  60.00   52
 14  ω     89.00 178.00   1.00    1.00    --  107.58  30.00 150.00   89
 15  ω     47.00 132.00   1.00    1.00    --  107.58 -45.00  90.00   85
 16  ω     54.00 110.00   1.00    1.00    --  107.58-111.00  44.00   56
 17  ω     36.00 102.00   1.00    1.00    --  107.58 -94.00 120.00   66
 18  ω   -106.00 -36.00   1.00    1.00    --  -40.73 -38.00  30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0861180000
_diffrn_orient_matrix_UB_12      -0.1575941000
_diffrn_orient_matrix_UB_13      -0.0028278000
_diffrn_orient_matrix_UB_21      -0.0051203000
_diffrn_orient_matrix_UB_22      0.0162687000
_diffrn_orient_matrix_UB_23      0.1211409000
_diffrn_orient_matrix_UB_31      -0.2079064000
_diffrn_orient_matrix_UB_32      0.0526357000
_diffrn_orient_matrix_UB_33      -0.0248870000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2747
_reflns_number_total             3112
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.074
_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)+(0.0773P)²+0.4505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1460
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N6(H6A,H6B), N18(H18A), N22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N17(H17)
;
_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
N1 N 0.3907(3) -0.01518(18) 0.35558(13) 0.0262(4) Uani 1 1 d . . . . .
N2 N 0.4180(3) -0.12556(18) 0.28623(14) 0.0285(4) Uani 1 1 d . . . . .
N3 N 0.4300(3) -0.08057(18) 0.19159(14) 0.0271(4) Uani 1 1 d . . . . .
N4 N 0.4086(2) 0.06329(17) 0.19823(12) 0.0200(3) Uani 1 1 d . . . . .
N5 N 0.4132(2) 0.14468(18) 0.11114(13) 0.0234(4) Uani 1 1 d . . . . .
N6 N 0.4491(3) 0.3245(2) -0.04543(14) 0.0288(4) Uani 1 1 d . . . . .
H6A H 0.502370 0.242859 -0.036650 0.035 Uiso 1 1 d R U . . .
H6B H 0.351089 0.313235 -0.097686 0.035 Uiso 1 1 d R U . . .
N7 N 0.3843(3) 0.3703(2) 0.05055(14) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.411(4) 0.456(3) 0.069(2) 0.030(6) Uiso 1 1 d . . . . .
N8 N 0.3482(2) 0.48875(19) 0.23844(14) 0.0260(4) Uani 1 1 d . . . . .
N9 N 0.3189(3) 0.5582(2) 0.32736(16) 0.0312(4) Uani 1 1 d . . . . .
H9A H 0.328(5) 0.506(4) 0.391(3) 0.070(11) Uiso 1 1 d . . . . .
H9B H 0.332(5) 0.653(4) 0.317(3) 0.062(10) Uiso 1 1 d . . . . .
N10 N 0.3235(2) 0.30168(18) 0.41860(13) 0.0239(4) Uani 1 1 d . . . . .
N11 N 0.3290(3) 0.2136(2) 0.49872(14) 0.0314(4) Uani 1 1 d . . . . .
H11A H 0.298(4) 0.249(3) 0.558(2) 0.044(8) Uiso 1 1 d . . . . .
H11B H 0.394(5) 0.124(4) 0.499(3) 0.060(9) Uiso 1 1 d . . . . .
C1 C 0.3866(3) 0.2823(2) 0.13154(16) 0.0218(4) Uani 1 1 d . . . . .
C2 C 0.3591(3) 0.3469(2) 0.23661(16) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.3548(3) 0.2521(2) 0.32496(16) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.3849(3) 0.1023(2) 0.29886(15) 0.0209(4) Uani 1 1 d . . . . .
N12 N 0.1760(2) 0.56420(19) 0.60669(13) 0.0261(4) Uani 1 1 d . . . . .
N13 N 0.1845(3) 0.42891(19) 0.64320(14) 0.0293(4) Uani 1 1 d . . . . .
N14 N 0.1662(3) 0.42739(18) 0.74430(14) 0.0271(4) Uani 1 1 d . . . . .
N15 N 0.1439(2) 0.56559(18) 0.77398(12) 0.0209(3) Uani 1 1 d . . . . .
N16 N 0.1252(2) 0.60253(17) 0.87793(12) 0.0210(3) Uani 1 1 d . . . . .
N17 N 0.0836(2) 0.78904(18) 0.99162(13) 0.0232(4) Uani 1 1 d . . . . .
H17 H 0.078765 0.882746 1.004765 0.028 Uiso 1 1 calc R U . . .
N18 N 0.0697(3) 0.69601(19) 1.07538(13) 0.0251(4) Uani 1 1 d . . . . .
H18A H 0.180802 0.657993 1.096917 0.030 Uiso 1 1 d R U . . .
H18B H -0.011(4) 0.628(3) 1.051(2) 0.035(7) Uiso 1 1 d . . . . .
N19 N 0.0640(2) 0.98134(18) 0.84320(13) 0.0212(3) Uani 1 1 d . . . . .
N20 N 0.0633(3) 1.08953(19) 0.77832(15) 0.0263(4) Uani 1 1 d . . . . .
H20A H 0.085(4) 1.080(3) 0.712(2) 0.048(8) Uiso 1 1 d . . . . .
H20B H 0.023(4) 1.163(3) 0.801(2) 0.035(7) Uiso 1 1 d . . . . .
N21 N 0.1446(2) 0.89542(19) 0.62899(13) 0.0259(4) Uani 1 1 d . . . . .
N22 N 0.1722(3) 0.8445(2) 0.53155(14) 0.0327(4) Uani 1 1 d . . . . .
H22A H 0.111214 0.760338 0.516125 0.039 Uiso 1 1 d R U . . .
H22B H 0.127115 0.903361 0.483829 0.039 Uiso 1 1 d R U . . .
C5 C 0.1510(3) 0.6486(2) 0.69027(15) 0.0205(4) Uani 1 1 d . . . . .
C6 C 0.1340(3) 0.8035(2) 0.70348(15) 0.0205(4) Uani 1 1 d . . . . .
C7 C 0.1006(3) 0.8507(2) 0.81057(14) 0.0191(4) Uani 1 1 d . . . . .
C8 C 0.1039(3) 0.7419(2) 0.89259(14) 0.0189(4) 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 N2 1.362(2) . ?
N1 C4 1.327(2) . ?
N2 N3 1.299(2) . ?
N3 N4 1.350(2) . ?
N4 N5 1.365(2) . ?
N4 C4 1.348(2) . ?
N5 C1 1.319(3) . ?
N6 H6A 0.8641 . ?
N6 H6B 0.8642 . ?
N6 N7 1.422(2) . ?
N7 H7 0.82(3) . ?
N7 C1 1.334(3) . ?
N8 N9 1.324(2) . ?
N8 C2 1.320(3) . ?
N9 H9A 0.95(4) . ?
N9 H9B 0.89(4) . ?
N10 N11 1.325(2) . ?
N10 C3 1.310(3) . ?
N11 H11A 0.87(3) . ?
N11 H11B 0.97(4) . ?
C1 C2 1.481(3) . ?
C2 C3 1.453(3) . ?
C3 C4 1.448(3) . ?
N12 N13 1.355(3) . ?
N12 C5 1.330(2) . ?
N13 N14 1.307(2) . ?
N14 N15 1.343(2) . ?
N15 N16 1.375(2) . ?
N15 C5 1.341(2) . ?
N16 C8 1.316(2) . ?
N17 H17 0.8800 . ?
N17 N18 1.406(2) . ?
N17 C8 1.342(2) . ?
N18 H18A 0.8748 . ?
N18 H18B 0.83(3) . ?
N19 N20 1.322(2) . ?
N19 C7 1.314(2) . ?
N20 H20A 0.88(3) . ?
N20 H20B 0.81(3) . ?
N21 N22 1.349(2) . ?
N21 C6 1.305(2) . ?
N22 H22A 0.8631 . ?
N22 H22B 0.8629 . ?
C5 C6 1.450(3) . ?
C6 C7 1.466(2) . ?
C7 C8 1.475(2) . ?

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
C4 N1 N2 105.31(16) . . ?
N3 N2 N1 111.78(16) . . ?
N2 N3 N4 105.68(15) . . ?
N3 N4 N5 120.74(15) . . ?
C4 N4 N3 108.91(15) . . ?
C4 N4 N5 130.35(16) . . ?
C1 N5 N4 112.56(16) . . ?
H6A N6 H6B 109.0 . . ?
N7 N6 H6A 109.6 . . ?
N7 N6 H6B 109.9 . . ?
N6 N7 H7 115.0(18) . . ?
C1 N7 N6 120.69(17) . . ?
C1 N7 H7 114.4(18) . . ?
C2 N8 N9 119.36(17) . . ?
N8 N9 H9A 118(2) . . ?
N8 N9 H9B 107(2) . . ?
H9A N9 H9B 132(3) . . ?
C3 N10 N11 119.65(17) . . ?
N10 N11 H11A 116.4(19) . . ?
N10 N11 H11B 122.3(19) . . ?
H11A N11 H11B 120(3) . . ?
N5 C1 N7 117.07(17) . . ?
N5 C1 C2 125.42(17) . . ?
N7 C1 C2 117.51(17) . . ?
N8 C2 C1 113.86(17) . . ?
N8 C2 C3 127.71(18) . . ?
C3 C2 C1 118.38(17) . . ?
N10 C3 C2 121.27(17) . . ?
N10 C3 C4 124.55(18) . . ?
C4 C3 C2 114.18(17) . . ?
N1 C4 N4 108.32(17) . . ?
N1 C4 C3 132.59(18) . . ?
N4 C4 C3 119.06(17) . . ?
C5 N12 N13 105.20(16) . . ?
N14 N13 N12 111.80(16) . . ?
N13 N14 N15 105.31(16) . . ?
N14 N15 N16 120.26(15) . . ?
C5 N15 N14 109.33(15) . . ?
C5 N15 N16 130.38(16) . . ?
C8 N16 N15 112.06(15) . . ?
N18 N17 H17 118.4 . . ?
C8 N17 H17 118.4 . . ?
C8 N17 N18 123.19(16) . . ?
N17 N18 H18A 111.3 . . ?
N17 N18 H18B 107.3(18) . . ?
H18A N18 H18B 106.9 . . ?
C7 N19 N20 120.39(16) . . ?
N19 N20 H20A 123(2) . . ?
N19 N20 H20B 114.2(19) . . ?
H20A N20 H20B 122(3) . . ?
C6 N21 N22 118.47(18) . . ?
N21 N22 H22A 109.9 . . ?
N21 N22 H22B 109.2 . . ?
H22A N22 H22B 109.1 . . ?
N12 C5 N15 108.36(17) . . ?
N12 C5 C6 132.16(17) . . ?
N15 C5 C6 119.47(16) . . ?
N21 C6 C5 124.93(17) . . ?
N21 C6 C7 121.46(18) . . ?
C5 C6 C7 113.61(16) . . ?
N19 C7 C6 127.30(17) . . ?
N19 C7 C8 114.54(16) . . ?
C6 C7 C8 118.15(16) . . ?
N16 C8 N17 116.74(16) . . ?
N16 C8 C7 126.14(17) . . ?
N17 C8 C7 117.11(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 -0.5(2) . . . . ?
N2 N1 C4 N4 -0.1(2) . . . . ?
N2 N1 C4 C3 178.1(2) . . . . ?
N2 N3 N4 N5 -179.74(16) . . . . ?
N2 N3 N4 C4 0.4(2) . . . . ?
N3 N4 N5 C1 178.90(16) . . . . ?
N3 N4 C4 N1 -0.2(2) . . . . ?
N3 N4 C4 C3 -178.68(16) . . . . ?
N4 N5 C1 N7 -178.55(15) . . . . ?
N4 N5 C1 C2 1.4(3) . . . . ?
N5 N4 C4 N1 179.97(17) . . . . ?
N5 N4 C4 C3 1.4(3) . . . . ?
N5 C1 C2 N8 175.74(17) . . . . ?
N5 C1 C2 C3 -1.9(3) . . . . ?
N6 N7 C1 N5 -13.1(3) . . . . ?
N6 N7 C1 C2 166.90(16) . . . . ?
N7 C1 C2 N8 -4.3(2) . . . . ?
N7 C1 C2 C3 178.05(16) . . . . ?
N8 C2 C3 N10 5.3(3) . . . . ?
N8 C2 C3 C4 -175.45(18) . . . . ?
N9 N8 C2 C1 178.37(16) . . . . ?
N9 N8 C2 C3 -4.2(3) . . . . ?
N10 C3 C4 N1 -0.6(3) . . . . ?
N10 C3 C4 N4 177.54(17) . . . . ?
N11 N10 C3 C2 -177.05(17) . . . . ?
N11 N10 C3 C4 3.8(3) . . . . ?
C1 C2 C3 N10 -177.36(16) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C2 C3 C4 N1 -179.7(2) . . . . ?
C2 C3 C4 N4 -1.6(3) . . . . ?
C4 N1 N2 N3 0.4(2) . . . . ?
C4 N4 N5 C1 -1.2(3) . . . . ?
N12 N13 N14 N15 0.4(2) . . . . ?
N12 C5 C6 N21 -1.4(3) . . . . ?
N12 C5 C6 C7 178.01(19) . . . . ?
N13 N12 C5 N15 -0.3(2) . . . . ?
N13 N12 C5 C6 179.0(2) . . . . ?
N13 N14 N15 N16 -178.47(16) . . . . ?
N13 N14 N15 C5 -0.6(2) . . . . ?
N14 N15 N16 C8 -179.73(16) . . . . ?
N14 N15 C5 N12 0.6(2) . . . . ?
N14 N15 C5 C6 -178.85(16) . . . . ?
N15 N16 C8 N17 179.74(15) . . . . ?
N15 N16 C8 C7 -0.4(3) . . . . ?
N15 C5 C6 N21 177.85(17) . . . . ?
N15 C5 C6 C7 -2.7(3) . . . . ?
N16 N15 C5 N12 178.17(17) . . . . ?
N16 N15 C5 C6 -1.3(3) . . . . ?
N18 N17 C8 N16 -4.9(3) . . . . ?
N18 N17 C8 C7 175.19(16) . . . . ?
N19 C7 C8 N16 175.56(17) . . . . ?
N19 C7 C8 N17 -4.5(2) . . . . ?
N20 N19 C7 C6 -3.3(3) . . . . ?
N20 N19 C7 C8 177.83(16) . . . . ?
N21 C6 C7 N19 5.3(3) . . . . ?
N21 C6 C7 C8 -175.87(16) . . . . ?
N22 N21 C6 C5 0.5(3) . . . . ?
N22 N21 C6 C7 -178.89(16) . . . . ?
C5 N12 N13 N14 -0.1(2) . . . . ?
C5 N15 N16 C8 2.9(3) . . . . ?
C5 C6 C7 N19 -174.13(17) . . . . ?
C5 C6 C7 C8 4.7(2) . . . . ?
C6 C7 C8 N16 -3.4(3) . . . . ?
C6 C7 C8 N17 176.49(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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.293
####################################################################### 
# 
# 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_20240321-1
_database_code_depnum_ccdc_archive 'CCDC 2403774'
loop_
_audit_author_name
_audit_author_address
'yingle liu'
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-03-02 downloaded from the CCDC.
;
_audit_creation_date             2024-03-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2 H6 O S), C6 H4 N12 O4'
_chemical_formula_sum            'C10 H16 N12 O6 S2'
_chemical_formula_weight         464.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.46862(13)
_cell_length_b                   9.56166(14)
_cell_length_c                   12.6797(2)
_cell_angle_alpha                94.2177(13)
_cell_angle_beta                 109.0415(15)
_cell_angle_gamma                90.5089(12)
_cell_volume                     967.33(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9560
_cell_measurement_theta_min      3.6870
_shelx_estimated_absorpt_T_max   0.750
_shelx_estimated_absorpt_T_min   0.693
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10095
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.157
_diffrn_reflns_theta_min         3.700
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    108.00 169.00   0.50    0.30    --   99.00  96.00 155.00  122
  2  ω     32.00  62.00   0.50    0.30    --   99.00 -61.00 -90.00   60
  3  ω     68.00 104.00   0.50    0.30    --   99.00 -77.00-150.00   72
  4  ω     32.00  64.00   0.50    0.30    --   99.00 -77.00-150.00   64
  5  ω     27.00  52.00   0.50    0.30    --   99.00 -45.00-180.00   50
  6  ω     27.00  53.00   0.50    0.30    --   99.00 -45.00-150.00   52
  7  ω     27.00  52.00   0.50    0.30    --   99.00 -45.00-120.00   50
  8  ω     27.00  52.00   0.50    0.30    --   99.00 -45.00 -60.00   50
  9  ω     27.00  52.00   0.50    0.20    --   45.75 -96.00  46.00   50
 10  ω     58.00 106.00   0.50    0.30    --   99.00 -96.00  46.00   96
 11  ω    -24.00   1.00   0.50    0.20    --  -45.75  19.00-150.00   50
 12  ω   -105.00 -79.00   0.50    0.30    --  -99.00 125.00-180.00   52
 13  ω    -76.00  24.00   0.50    0.20    --  -45.75  96.00 155.00  200
 14  ω   -101.00 -59.00   0.50    0.30    --  -99.00  96.00 155.00   84
 15  ω    -68.00 -42.00   0.50    0.30    --  -99.00  61.00 120.00   52
 16  ω    -68.00 -26.00   0.50    0.30    --  -99.00  61.00 150.00   84
 17  ω   -101.00 -73.00   0.50    0.30    --  -99.00  77.00   0.00   56
 18  ω    -66.00 -34.00   0.50    0.30    --  -99.00  61.00 -90.00   64
 19  ω    -64.00 -35.00   0.50    0.30    --  -99.00  77.00   0.00   58
 20  ω    -67.00 -26.00   0.50    0.30    --  -99.00  61.00   0.00   82
 21  ω    -58.00 -32.00   0.50    0.30    --  -99.00  61.00  90.00   52
 22  ω   -119.00 -22.00   0.50    0.20    --  -45.75 -77.00  60.00  194
 23  ω   -170.00 -99.00   0.50    0.30    --  -99.00 -96.00  46.00  142
 24  ω     38.00  67.00   0.50    0.10    --   45.87 -77.00 150.00   58
 25  ω     33.00 110.00   0.50    0.10    --   45.87  57.00 -90.00  154
 26  ω   -169.00-140.00   0.50    0.20    --  -99.00 -30.00  60.00   58
 27  ω    -84.00 -58.00   0.50    0.20    --  -99.00  77.00 -30.00   52
 28  ω   -148.00-117.00   0.50    0.20    --  -99.00 -45.00 -90.00   62
 29  ω   -115.00 -90.00   0.50    0.20    --  -99.00 -45.00 -90.00   50
 30  ω   -137.00-102.00   0.50    0.20    --  -99.00 -30.00  60.00   70
 31  ω   -137.00 -93.00   0.50    0.20    --  -99.00 -30.00 120.00   88
 32  ω   -112.00 -68.00   0.50    0.20    --  -99.00 125.00 150.00   88
 33  ω   -140.00-112.00   0.50    0.20    --  -99.00 -45.00 -30.00   56
 34  ω   -172.00-145.00   0.50    0.20    --  -99.00 -30.00 120.00   54
 35  ω   -106.00 -81.00   0.50    0.20    --  -99.00 -15.00   0.00   50
 36  ω   -174.00-148.00   0.50    0.20    --  -99.00 -15.00   0.00   52
 37  ω   -112.00 -87.00   0.50    0.20    --  -99.00 125.00 -30.00   50
 38  ω     27.00  52.00   0.50    0.20    --   99.00 -45.00 120.00   50
 39  ω     71.00 112.00   0.50    0.20    --   99.00-125.00  30.00   82
 40  ω     74.00 101.00   0.50    0.20    --   99.00 -94.00-120.00   54
 41  ω     29.00  60.00   0.50    0.20    --   99.00 -94.00-120.00   62
 42  ω    135.00 164.00   0.50    0.20    --   99.00 125.00-120.00   58
 43  ω     79.00 132.00   0.50    0.20    --   99.00 125.00-120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0926183000
_diffrn_orient_matrix_UB_12      0.0429040000
_diffrn_orient_matrix_UB_13      0.1247039000
_diffrn_orient_matrix_UB_21      -0.1533471000
_diffrn_orient_matrix_UB_22      -0.0492575000
_diffrn_orient_matrix_UB_23      0.0291733000
_diffrn_orient_matrix_UB_31      0.0706143000
_diffrn_orient_matrix_UB_32      -0.1478687000
_diffrn_orient_matrix_UB_33      0.0150637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3694
_reflns_number_total             3754
_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.0135(8)
_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   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.7551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1066
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C9(H,HA,HB), C10(HC,HD,HE), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.04306(5) 0.73175(4) 0.73599(4) 0.01338(14) Uani 1 1 d . . . . .
O6 O 1.05735(16) 0.57982(13) 0.69793(11) 0.0166(3) Uani 1 1 d . . . . .
C9 C 1.2020(2) 0.83311(19) 0.70859(16) 0.0163(4) Uani 1 1 d . . . . .
H H 1.309930 0.800998 0.750108 0.024 Uiso 1 1 calc R U . . .
HA H 1.194124 0.930216 0.730940 0.024 Uiso 1 1 calc R U . . .
HB H 1.187202 0.822482 0.630038 0.024 Uiso 1 1 calc R U . . .
C10 C 1.1339(3) 0.7442(2) 0.88497(17) 0.0228(4) Uani 1 1 d . . . . .
HC H 1.066250 0.690538 0.916201 0.034 Uiso 1 1 calc R U . . .
HD H 1.139992 0.840670 0.913445 0.034 Uiso 1 1 calc R U . . .
HE H 1.244367 0.708154 0.905308 0.034 Uiso 1 1 calc R U . . .
S2 S 0.40520(5) 0.89733(4) 0.34756(4) 0.01398(15) Uani 1 1 d . . . . .
O5 O 0.36374(17) 0.74103(13) 0.33353(11) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.2356(2) 0.9788(2) 0.37851(18) 0.0205(4) Uani 1 1 d . . . . .
H7A H 0.132333 0.946613 0.322568 0.031 Uiso 1 1 calc R U . . .
H7B H 0.248076 1.078787 0.379040 0.031 Uiso 1 1 calc R U . . .
H7C H 0.235033 0.955028 0.450629 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3616(3) 0.9509(2) 0.20898(17) 0.0242(4) Uani 1 1 d . . . . .
H8A H 0.436951 0.907025 0.175302 0.036 Uiso 1 1 calc R U . . .
H8B H 0.375815 1.050976 0.212211 0.036 Uiso 1 1 calc R U . . .
H8C H 0.248592 0.923300 0.165042 0.036 Uiso 1 1 calc R U . . .
O1 O 0.53321(19) 0.25744(15) 0.42920(12) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.33158(16) 0.30653(14) 0.28305(12) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.35842(19) 0.08683(15) -0.05849(13) 0.0254(3) Uani 1 1 d . . . . .
O4 O 0.09473(17) 0.13267(16) -0.10268(12) 0.0250(3) Uani 1 1 d . . . . .
N1 N 0.8887(2) 0.72380(16) 0.47920(13) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.9035(2) 0.82471(17) 0.41310(14) 0.0207(4) Uani 1 1 d . . . . .
N3 N 0.8056(2) 0.79845(17) 0.30999(14) 0.0192(3) Uani 1 1 d . . . . .
N4 N 0.72377(18) 0.67676(15) 0.30923(12) 0.0124(3) Uani 1 1 d . . . . .
N5 N 0.60966(19) 0.61699(16) 0.21463(12) 0.0133(3) Uani 1 1 d . . . . .
N6 N 0.75984(19) 0.46229(15) 0.53637(12) 0.0130(3) Uani 1 1 d . . . . .
H6A H 0.714999 0.389419 0.552629 0.016 Uiso 1 1 calc R U . . .
H6B H 0.841907 0.507433 0.586515 0.016 Uiso 1 1 calc R U . . .
N7 N 0.47175(19) 0.33056(15) 0.35030(13) 0.0129(3) Uani 1 1 d . . . . .
N8 N 0.41233(18) 0.44520(15) 0.13729(12) 0.0126(3) Uani 1 1 d . . . . .
N9 N 0.43420(19) 0.31577(16) 0.08926(13) 0.0148(3) Uani 1 1 d . . . . .
N10 N 0.16703(18) 0.38771(16) 0.01188(12) 0.0129(3) Uani 1 1 d . . . . .
N11 N 0.18903(19) 0.59893(16) 0.12833(13) 0.0171(3) Uani 1 1 d . . . . .
H11A H 0.085605 0.617311 0.097747 0.021 Uiso 1 1 calc R U . . .
H11B H 0.252844 0.654995 0.181643 0.021 Uiso 1 1 calc R U . . .
N12 N 0.2434(2) 0.16125(16) -0.05408(13) 0.0162(3) Uani 1 1 d . . . . .
C1 C 0.7760(2) 0.63185(18) 0.41298(14) 0.0111(3) Uani 1 1 d . . . . .
C2 C 0.7028(2) 0.50475(17) 0.43466(14) 0.0106(3) Uani 1 1 d . . . . .
C3 C 0.5714(2) 0.44803(17) 0.34034(14) 0.0102(3) Uani 1 1 d . . . . .
C4 C 0.5363(2) 0.50670(18) 0.23464(14) 0.0108(3) Uani 1 1 d . . . . .
C5 C 0.2501(2) 0.48417(18) 0.09328(14) 0.0119(3) Uani 1 1 d . . . . .
C6 C 0.2850(2) 0.29229(18) 0.01628(14) 0.0125(3) 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
S1 O6 1.5152(13) . ?
S1 C9 1.7897(19) . ?
S1 C10 1.786(2) . ?
C9 H 0.9600 . ?
C9 HA 0.9600 . ?
C9 HB 0.9600 . ?
C10 HC 0.9600 . ?
C10 HD 0.9600 . ?
C10 HE 0.9600 . ?
S2 O5 1.5163(13) . ?
S2 C7 1.7792(19) . ?
S2 C8 1.788(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O1 N7 1.237(2) . ?
O2 N7 1.223(2) . ?
O3 N12 1.225(2) . ?
O4 N12 1.225(2) . ?
N1 N2 1.354(2) . ?
N1 C1 1.320(2) . ?
N2 N3 1.304(2) . ?
N3 N4 1.347(2) . ?
N4 N5 1.354(2) . ?
N4 C1 1.348(2) . ?
N5 C4 1.301(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C2 1.317(2) . ?
N7 C3 1.437(2) . ?
N8 N9 1.380(2) . ?
N8 C4 1.417(2) . ?
N8 C5 1.370(2) . ?
N9 C6 1.306(2) . ?
N10 C5 1.336(2) . ?
N10 C6 1.349(2) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N11 C5 1.326(2) . ?
N12 C6 1.453(2) . ?
C1 C2 1.444(2) . ?
C2 C3 1.410(2) . ?
C3 C4 1.433(2) . ?

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
O6 S1 C9 108.01(8) . . ?
O6 S1 C10 105.63(9) . . ?
C10 S1 C9 96.95(9) . . ?
S1 C9 H 109.5 . . ?
S1 C9 HA 109.5 . . ?
S1 C9 HB 109.5 . . ?
H C9 HA 109.5 . . ?
H C9 HB 109.5 . . ?
HA C9 HB 109.5 . . ?
S1 C10 HC 109.5 . . ?
S1 C10 HD 109.5 . . ?
S1 C10 HE 109.5 . . ?
HC C10 HD 109.5 . . ?
HC C10 HE 109.5 . . ?
HD C10 HE 109.5 . . ?
O5 S2 C7 105.74(9) . . ?
O5 S2 C8 105.72(9) . . ?
C7 S2 C8 97.97(10) . . ?
S2 C7 H7A 109.5 . . ?
S2 C7 H7B 109.5 . . ?
S2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
S2 C8 H8A 109.5 . . ?
S2 C8 H8B 109.5 . . ?
S2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 N2 105.44(15) . . ?
N3 N2 N1 111.99(15) . . ?
N2 N3 N4 105.14(14) . . ?
N3 N4 N5 121.61(14) . . ?
N3 N4 C1 109.08(14) . . ?
C1 N4 N5 129.32(15) . . ?
C4 N5 N4 111.35(14) . . ?
H6A N6 H6B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
O1 N7 C3 117.31(15) . . ?
O2 N7 O1 122.45(15) . . ?
O2 N7 C3 120.24(15) . . ?
N9 N8 C4 120.82(14) . . ?
C5 N8 N9 110.59(14) . . ?
C5 N8 C4 127.18(14) . . ?
C6 N9 N8 99.73(14) . . ?
C5 N10 C6 101.77(14) . . ?
H11A N11 H11B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
O3 N12 O4 125.12(16) . . ?
O3 N12 C6 117.86(16) . . ?
O4 N12 C6 117.01(15) . . ?
N1 C1 N4 108.34(15) . . ?
N1 C1 C2 131.91(16) . . ?
N4 C1 C2 119.70(15) . . ?
N6 C2 C1 117.99(15) . . ?
N6 C2 C3 129.80(16) . . ?
C3 C2 C1 112.14(15) . . ?
C2 C3 N7 119.74(15) . . ?
C2 C3 C4 120.57(15) . . ?
C4 C3 N7 119.69(15) . . ?
N5 C4 N8 112.25(15) . . ?
N5 C4 C3 126.45(16) . . ?
N8 C4 C3 121.30(15) . . ?
N10 C5 N8 108.78(15) . . ?
N11 C5 N8 124.34(16) . . ?
N11 C5 N10 126.88(16) . . ?
N9 C6 N10 118.98(16) . . ?
N9 C6 N12 120.49(15) . . ?
N10 C6 N12 120.40(16) . . ?

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 N7 C3 C2 -21.4(2) . . . . ?
O1 N7 C3 C4 158.76(16) . . . . ?
O2 N7 C3 C2 158.06(15) . . . . ?
O2 N7 C3 C4 -21.8(2) . . . . ?
O3 N12 C6 N9 -13.8(3) . . . . ?
O3 N12 C6 N10 170.26(17) . . . . ?
O4 N12 C6 N9 164.73(17) . . . . ?
O4 N12 C6 N10 -11.2(2) . . . . ?
N1 N2 N3 N4 0.4(2) . . . . ?
N1 C1 C2 N6 -4.4(3) . . . . ?
N1 C1 C2 C3 172.88(18) . . . . ?
N2 N1 C1 N4 -0.1(2) . . . . ?
N2 N1 C1 C2 -177.60(18) . . . . ?
N2 N3 N4 N5 179.83(15) . . . . ?
N2 N3 N4 C1 -0.5(2) . . . . ?
N3 N4 N5 C4 -174.78(15) . . . . ?
N3 N4 C1 N1 0.4(2) . . . . ?
N3 N4 C1 C2 178.20(15) . . . . ?
N4 N5 C4 N8 178.04(13) . . . . ?
N4 N5 C4 C3 -2.5(2) . . . . ?
N4 C1 C2 N6 178.38(15) . . . . ?
N4 C1 C2 C3 -4.3(2) . . . . ?
N5 N4 C1 N1 -179.93(16) . . . . ?
N5 N4 C1 C2 -2.1(3) . . . . ?
N6 C2 C3 N7 3.9(3) . . . . ?
N6 C2 C3 C4 -176.23(16) . . . . ?
N7 C3 C4 N5 176.06(16) . . . . ?
N7 C3 C4 N8 -4.5(2) . . . . ?
N8 N9 C6 N10 -1.5(2) . . . . ?
N8 N9 C6 N12 -177.52(15) . . . . ?
N9 N8 C4 N5 111.33(18) . . . . ?
N9 N8 C4 C3 -68.2(2) . . . . ?
N9 N8 C5 N10 -4.1(2) . . . . ?
N9 N8 C5 N11 175.32(17) . . . . ?
C1 N1 N2 N3 -0.1(2) . . . . ?
C1 N4 N5 C4 5.6(2) . . . . ?
C1 C2 C3 N7 -172.99(14) . . . . ?
C1 C2 C3 C4 6.9(2) . . . . ?
C2 C3 C4 N5 -3.8(3) . . . . ?
C2 C3 C4 N8 175.65(15) . . . . ?
C4 N8 N9 C6 170.72(16) . . . . ?
C4 N8 C5 N10 -170.56(16) . . . . ?
C4 N8 C5 N11 8.9(3) . . . . ?
C5 N8 N9 C6 3.30(19) . . . . ?
C5 N8 C4 N5 -83.5(2) . . . . ?
C5 N8 C4 C3 97.0(2) . . . . ?
C5 N10 C6 N9 -0.8(2) . . . . ?
C5 N10 C6 N12 175.16(16) . . . . ?
C6 N10 C5 N8 2.90(19) . . . . ?
C6 N10 C5 N11 -176.54(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 7.087
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_sc0710
_database_code_depnum_ccdc_archive 'CCDC 2403773'
loop_
_audit_author_name
_audit_author_address
'yingle liu'
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-03-02 downloaded from the CCDC.
;
_audit_creation_date             2023-07-11
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H5 N15 O4'
_chemical_formula_sum            'C8 H5 N15 O4'
_chemical_formula_weight         375.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.8589(11)
_cell_length_b                   5.4874(3)
_cell_length_c                   13.0739(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.405(6)
_cell_angle_gamma                90
_cell_volume                     1321.38(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1449
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.4390
_cell_measurement_theta_min      2.3630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4459
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.785
_diffrn_reflns_theta_min         2.399
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -6.00   1.00    1.50    --  -40.73 125.00   0.00   26
  2  ω   -114.00 -18.00   1.00    1.50    --  -40.73 -37.00-180.00   96
  3  ω   -114.00 -34.00   1.00    1.50    --  -40.73 -37.00 -90.00   80
  4  ω    103.00 135.00   1.00    2.00    --  107.58 -77.00 -90.00   32
  5  ω     80.00 178.00   1.00    2.00    --  107.58  30.00-150.00   98
  6  ω    127.00 154.00   1.00    2.00    --  107.58  45.00-180.00   27
  7  ω    110.00 143.00   1.00    2.00    --  107.58 125.00  30.00   33
  8  ω    144.00 169.00   1.00    2.00    --  107.58 125.00  30.00   25
  9  ω     44.00 132.00   1.00    2.00    --  107.58 -45.00  30.00   88
 10  ω     44.00  71.00   1.00    2.00    --  107.58 -77.00 -90.00   27
 11  ω     25.00 104.00   1.00    2.00    --  107.58 -94.00 -30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0416656000
_diffrn_orient_matrix_UB_12      -0.0149834000
_diffrn_orient_matrix_UB_13      -0.0890666000
_diffrn_orient_matrix_UB_21      -0.0684559000
_diffrn_orient_matrix_UB_22      -0.1006972000
_diffrn_orient_matrix_UB_23      -0.0740396000
_diffrn_orient_matrix_UB_31      -0.0238741000
_diffrn_orient_matrix_UB_32      0.2617364000
_diffrn_orient_matrix_UB_33      -0.0337222000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2036
_reflns_number_total             2591
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.053
_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)+(0.0786P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1586
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
2. Others
 Sof(O5)=1-FVAR(1)
 Sof(O4)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N8(H8)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N15(H15A,H15B)
;
_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
O1 O 0.16676(11) 0.7084(4) 0.02738(13) 0.0269(5) Uani 1 1 d . . . . .
O2 O 0.21926(11) 0.8460(3) 0.17908(14) 0.0221(4) Uani 1 1 d . . . . .
O3 O 0.32931(12) 0.9260(4) 0.33734(16) 0.0321(5) Uani 1 1 d . . . . .
O4 O 0.4242(8) 0.978(3) 0.4522(10) 0.041(3) Uani 0.59(5) 1 d . . P A 1
O5 O 0.4442(10) 0.882(6) 0.4229(17) 0.048(6) Uani 0.41(5) 1 d . . P A 2
N1 N 0.18395(12) 0.6857(4) 0.12323(16) 0.0198(5) Uani 1 1 d . . . . .
N2 N 0.07658(12) 0.3483(4) 0.00803(16) 0.0213(5) Uani 1 1 d . . . . .
H2A H 0.089433 0.467601 -0.029158 0.026 Uiso 1 1 calc R U . . .
H2B H 0.043364 0.242738 -0.021711 0.026 Uiso 1 1 calc R U . . .
N3 N 0.03368(12) -0.0435(4) 0.13422(15) 0.0186(5) Uani 1 1 d . . . . .
N4 N 0.03393(12) -0.1751(4) 0.22181(16) 0.0201(5) Uani 1 1 d . . . . .
N5 N 0.08116(12) -0.0899(4) 0.30237(16) 0.0190(5) Uani 1 1 d . . . . .
N6 N 0.11188(11) 0.1025(4) 0.26603(15) 0.0157(4) Uani 1 1 d . . . . .
N7 N 0.16512(11) 0.2317(4) 0.32884(15) 0.0175(5) Uani 1 1 d . . . . .
N8 N 0.24638(12) 0.5460(4) 0.33745(15) 0.0189(5) Uani 1 1 d . . . . .
H8 H 0.255013 0.686077 0.309657 0.023 Uiso 1 1 calc R U . . .
N9 N 0.37329(15) 0.8424(5) 0.41078(19) 0.0366(7) Uani 1 1 d . . . . .
N10 N 0.27392(12) 0.3043(4) 0.48515(16) 0.0211(5) Uani 1 1 d . . . . .
N11 N 0.32442(12) 0.2548(4) 0.57354(16) 0.0224(5) Uani 1 1 d . . . . .
N12 N 0.31658(14) 0.0649(5) 0.63547(18) 0.0300(6) Uani 1 1 d . . . . .
N13 N 0.37549(14) 0.0656(5) 0.71080(19) 0.0321(6) Uani 1 1 d . . . . .
N14 N 0.42039(13) 0.2470(5) 0.69866(19) 0.0299(6) Uani 1 1 d . . . . .
N15 N 0.47006(15) 0.6752(5) 0.6035(2) 0.0402(7) Uani 1 1 d . . . . .
H15A H 0.485359 0.803578 0.574203 0.048 Uiso 1 1 calc R U . . .
H15B H 0.496147 0.616404 0.662333 0.048 Uiso 1 1 calc R U . . .
C1 C 0.16071(14) 0.4747(4) 0.17070(18) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.10713(14) 0.3276(4) 0.10838(18) 0.0171(5) Uani 1 1 d . . . . .
C3 C 0.08257(13) 0.1302(4) 0.16421(18) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.18924(14) 0.4125(4) 0.28083(18) 0.0159(5) Uani 1 1 d . . . . .
C5 C 0.29169(14) 0.4887(5) 0.43187(19) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.35766(16) 0.6315(5) 0.4666(2) 0.0258(6) Uani 1 1 d . . . . .
C7 C 0.40795(16) 0.5707(6) 0.5594(2) 0.0276(6) Uani 1 1 d . . . . .
C8 C 0.38724(15) 0.3644(5) 0.6124(2) 0.0244(6) 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
O1 N1 1.231(3) . ?
O2 N1 1.242(3) . ?
O3 N9 1.216(3) . ?
O4 N9 1.242(6) . ?
O5 N9 1.330(17) . ?
N1 C1 1.427(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.320(3) . ?
N3 N4 1.353(3) . ?
N3 C3 1.325(3) . ?
N4 N5 1.311(3) . ?
N5 N6 1.340(3) . ?
N6 N7 1.353(3) . ?
N6 C3 1.336(3) . ?
N7 C4 1.307(3) . ?
N8 H8 0.8800 . ?
N8 C4 1.380(3) . ?
N8 C5 1.378(3) . ?
N9 C6 1.432(4) . ?
N10 N11 1.358(3) . ?
N10 C5 1.312(3) . ?
N11 N12 1.347(3) . ?
N11 C8 1.328(3) . ?
N12 N13 1.317(3) . ?
N13 N14 1.338(4) . ?
N14 C8 1.332(4) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N15 C7 1.320(4) . ?
C1 C2 1.408(3) . ?
C1 C4 1.465(3) . ?
C2 C3 1.438(3) . ?
C5 C6 1.458(4) . ?
C6 C7 1.409(4) . ?
C7 C8 1.425(4) . ?

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 N1 O2 121.2(2) . . ?
O1 N1 C1 119.1(2) . . ?
O2 N1 C1 119.7(2) . . ?
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
C3 N3 N4 104.93(19) . . ?
N5 N4 N3 111.6(2) . . ?
N4 N5 N6 105.50(19) . . ?
N5 N6 N7 121.25(19) . . ?
C3 N6 N5 109.0(2) . . ?
C3 N6 N7 129.8(2) . . ?
C4 N7 N6 113.30(19) . . ?
C4 N8 H8 115.8 . . ?
C5 N8 H8 115.8 . . ?
C5 N8 C4 128.4(2) . . ?
O3 N9 O4 116.7(5) . . ?
O3 N9 O5 122.0(4) . . ?
O3 N9 C6 121.8(2) . . ?
O4 N9 C6 119.1(3) . . ?
O5 N9 C6 112.6(8) . . ?
C5 N10 N11 113.2(2) . . ?
N12 N11 N10 121.2(2) . . ?
C8 N11 N10 129.8(2) . . ?
C8 N11 N12 108.9(2) . . ?
N13 N12 N11 105.3(2) . . ?
N12 N13 N14 111.5(2) . . ?
C8 N14 N13 105.4(2) . . ?
H15A N15 H15B 120.0 . . ?
C7 N15 H15A 120.0 . . ?
C7 N15 H15B 120.0 . . ?
N1 C1 C4 122.3(2) . . ?
C2 C1 N1 117.6(2) . . ?
C2 C1 C4 120.1(2) . . ?
N2 C2 C1 129.2(2) . . ?
N2 C2 C3 116.8(2) . . ?
C1 C2 C3 114.1(2) . . ?
N3 C3 N6 109.0(2) . . ?
N3 C3 C2 132.2(2) . . ?
N6 C3 C2 118.8(2) . . ?
N7 C4 N8 117.3(2) . . ?
N7 C4 C1 123.8(2) . . ?
N8 C4 C1 118.9(2) . . ?
N8 C5 C6 118.7(2) . . ?
N10 C5 N8 118.1(2) . . ?
N10 C5 C6 123.2(2) . . ?
N9 C6 C5 122.1(2) . . ?
C7 C6 N9 117.1(3) . . ?
C7 C6 C5 120.8(2) . . ?
N15 C7 C6 130.0(3) . . ?
N15 C7 C8 116.2(2) . . ?
C6 C7 C8 113.7(3) . . ?
N11 C8 N14 108.8(2) . . ?
N11 C8 C7 119.2(2) . . ?
N14 C8 C7 131.9(3) . . ?

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
N2 H2A O1 0.88 1.99 2.584(3) 123.8 . yes
N8 H8 O2 0.88 1.91 2.608(3) 135.2 . yes
N8 H8 O3 0.88 1.90 2.607(3) 136.1 . yes
N15 H15A O4 0.88 2.00 2.586(7) 122.9 . yes
N15 H15A O5 0.88 2.01 2.571(9) 120.5 . 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
O1 N1 C1 C2 -12.7(4) . . . . ?
O1 N1 C1 C4 168.9(2) . . . . ?
O2 N1 C1 C2 165.3(2) . . . . ?
O2 N1 C1 C4 -13.2(4) . . . . ?
O3 N9 C6 C5 7.0(5) . . . . ?
O3 N9 C6 C7 -171.1(3) . . . . ?
O4 N9 C6 C5 169.0(14) . . . . ?
O4 N9 C6 C7 -9.0(14) . . . . ?
O5 N9 C6 C5 -152.0(18) . . . . ?
O5 N9 C6 C7 30.0(19) . . . . ?
N1 C1 C2 N2 3.9(4) . . . . ?
N1 C1 C2 C3 -175.2(2) . . . . ?
N1 C1 C4 N7 174.5(2) . . . . ?
N1 C1 C4 N8 -7.6(4) . . . . ?
N2 C2 C3 N3 0.4(4) . . . . ?
N2 C2 C3 N6 -179.9(2) . . . . ?
N3 N4 N5 N6 0.4(3) . . . . ?
N4 N3 C3 N6 0.7(3) . . . . ?
N4 N3 C3 C2 -179.5(3) . . . . ?
N4 N5 N6 N7 -178.4(2) . . . . ?
N4 N5 N6 C3 0.1(3) . . . . ?
N5 N6 N7 C4 179.7(2) . . . . ?
N5 N6 C3 N3 -0.5(3) . . . . ?
N5 N6 C3 C2 179.7(2) . . . . ?
N6 N7 C4 N8 -176.6(2) . . . . ?
N6 N7 C4 C1 1.4(4) . . . . ?
N7 N6 C3 N3 177.8(2) . . . . ?
N7 N6 C3 C2 -2.1(4) . . . . ?
N8 C5 C6 N9 5.9(4) . . . . ?
N8 C5 C6 C7 -176.1(3) . . . . ?
N9 C6 C7 N15 -2.0(5) . . . . ?
N9 C6 C7 C8 177.7(3) . . . . ?
N10 N11 N12 N13 177.9(2) . . . . ?
N10 N11 C8 N14 -177.4(3) . . . . ?
N10 N11 C8 C7 1.8(5) . . . . ?
N10 C5 C6 N9 -175.5(3) . . . . ?
N10 C5 C6 C7 2.4(4) . . . . ?
N11 N10 C5 N8 176.2(2) . . . . ?
N11 N10 C5 C6 -2.3(4) . . . . ?
N11 N12 N13 N14 -0.4(3) . . . . ?
N12 N11 C8 N14 0.3(3) . . . . ?
N12 N11 C8 C7 179.5(3) . . . . ?
N12 N13 N14 C8 0.5(3) . . . . ?
N13 N14 C8 N11 -0.5(3) . . . . ?
N13 N14 C8 C7 -179.5(3) . . . . ?
N15 C7 C8 N11 178.2(3) . . . . ?
N15 C7 C8 N14 -2.8(5) . . . . ?
C1 C2 C3 N3 179.6(2) . . . . ?
C1 C2 C3 N6 -0.6(3) . . . . ?
C2 C1 C4 N7 -3.9(4) . . . . ?
C2 C1 C4 N8 174.0(2) . . . . ?
C3 N3 N4 N5 -0.7(3) . . . . ?
C3 N6 N7 C4 1.6(4) . . . . ?
C4 N8 C5 N10 -11.4(4) . . . . ?
C4 N8 C5 C6 167.2(2) . . . . ?
C4 C1 C2 N2 -177.6(3) . . . . ?
C4 C1 C2 C3 3.2(3) . . . . ?
C5 N8 C4 N7 14.1(4) . . . . ?
C5 N8 C4 C1 -164.0(2) . . . . ?
C5 N10 N11 N12 -177.2(2) . . . . ?
C5 N10 N11 C8 0.2(4) . . . . ?
C5 C6 C7 N15 179.9(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 N11 -1.6(4) . . . . ?
C6 C7 C8 N14 177.4(3) . . . . ?
C8 N11 N12 N13 0.1(3) . . . . ?

_olex2_date_sample_data_collection 2023-07-10
_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.693
####################################################################### 
# 
# 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_exp_5694
_database_code_depnum_ccdc_archive 'CCDC 2403776'
loop_
_audit_author_name
_audit_author_address
'yingle liu'
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2024-11-19 deposited with the CCDC.	2025-03-02 downloaded from the CCDC.
;
_audit_creation_date             2024-11-13
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 N12 O4'
_chemical_formula_sum            'C7 H6 N12 O4'
_chemical_formula_weight         322.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.7964(13)
_cell_length_b                   7.5465(9)
_cell_length_c                   11.8598(18)
_cell_angle_alpha                107.140(12)
_cell_angle_beta                 96.176(14)
_cell_angle_gamma                92.491(12)
_cell_volume                     576.08(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1462
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      74.5520
_cell_measurement_theta_min      7.9370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3435
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.550
_diffrn_reflns_theta_max         66.550
_diffrn_reflns_theta_min         3.932
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00 112.00   1.00    1.50    --   40.73  38.00  60.00   83
  2  ω     97.00 124.00   1.00    2.00    --  109.45 -45.00  60.00   27
  3  ω     99.00 134.00   1.00    2.00    --  109.45 -45.00  30.00   35
  4  ω     72.00 119.00   1.00    2.00    --  109.45-125.00 -30.00   47
  5  ω     46.00  92.00   1.00    1.50    --   40.73-125.00  90.00   46
  6  ω     44.00  77.00   1.00    2.00    --  109.45 -45.00  60.00   33
  7  ω     41.00  80.00   1.00    2.00    --  109.45 -45.00  30.00   39
  8  ω     61.00 174.00   1.00    2.00    --  109.45  15.00 -60.00  113
  9  ω    123.00 176.00   1.00    2.00    --  109.45 125.00 -30.00   53
 10  ω    106.00 177.00   1.00    2.00    --  109.45 125.00-180.00   71
 11  ω     87.00 167.00   1.00    2.00    --  109.45  45.00   0.00   80
 12  ω     61.00 120.00   1.00    2.00    --  109.45-125.00-180.00   59
 13  ω     42.00 136.00   1.00    2.00    --  109.45 -61.00 -90.00   94
 14  ω     39.00  66.00   1.00   10.00    --  109.45-125.00 -30.00   27
 15  ω     35.00  62.00   1.00   10.00    --  109.45 -94.00 -90.00   27
 16  ω     29.00  63.00   1.00    5.00    --   40.73 -19.00   0.00   34
 17  ω    -72.00  20.00   1.00    5.00    --  -40.73  77.00 -60.00   92
 18  ω   -105.00 -17.00   1.00    5.00    --  -40.73 -57.00 150.00   88
 19  ω     97.00 123.00   1.00   10.00    --  108.20 -77.00 150.00   26
 20  ω     35.00  61.00   1.00   10.00    --  108.20 -94.00 -30.00   26
 21  ω     81.00 107.00   1.00   10.00    --  108.20 -94.00 -30.00   26
 22  ω     26.00  51.00   1.00   10.00    --  108.20 -94.00  60.00   25
 23  ω     46.00  72.00   1.00   10.00    --  108.20 -77.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1909426000
_diffrn_orient_matrix_UB_12      0.1010360000
_diffrn_orient_matrix_UB_13      0.0215582000
_diffrn_orient_matrix_UB_21      0.1031885000
_diffrn_orient_matrix_UB_22      0.1262195000
_diffrn_orient_matrix_UB_23      0.1208103000
_diffrn_orient_matrix_UB_31      0.0721274000
_diffrn_orient_matrix_UB_32      0.1406607000
_diffrn_orient_matrix_UB_33      -0.0609673000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1713
_reflns_number_total             1998
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.1211
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1711P)²+6.4519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3709
_refine_ls_wR_factor_ref         0.3758
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Rigid body (RIGU) restrains
 N12, O1, N7, O2, C3, C1, C4, N6, C2, N5, N8, H6A, H6B, N1, N4, N9, C5, N2, N3,
  C7, N11, C6, N10, H10A, H10B, O3, O4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.009
3.a X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N10(H10A,H10B), N11(H11A,H11B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.3207(6) 1.0058(4) 0.2553(3) 0.0352(8) Uani 1 1 d . . . . .
O2 O 0.4715(6) 0.8921(4) 0.3857(3) 0.0343(7) Uani 1 1 d . . . . .
O3 O 0.2691(6) 0.7437(5) 0.7972(3) 0.0389(9) Uani 1 1 d . . . . .
O4 O 0.3420(6) 0.4643(4) 0.7074(3) 0.0376(8) Uani 1 1 d . . . . .
N1 N 0.2252(7) 0.3471(5) -0.0640(3) 0.0326(9) Uani 1 1 d . . . . .
N2 N 0.2085(7) 0.1693(5) -0.0628(3) 0.0328(9) Uani 1 1 d . . . . .
N3 N 0.2033(7) 0.1575(5) 0.0441(3) 0.0320(9) Uani 1 1 d . . . . .
N4 N 0.2139(6) 0.3332(5) 0.1159(3) 0.0255(8) Uani 1 1 d . . . . .
N5 N 0.1950(6) 0.3783(5) 0.2330(3) 0.0273(8) Uani 1 1 d . . . . .
N6 N 0.2713(6) 0.7569(5) 0.0388(3) 0.0280(8) Uani 1 1 d . . . . .
H6A H 0.292675 0.877940 0.071943 0.034 Uiso 1 1 calc R U . . .
H6B H 0.260947 0.709549 -0.039047 0.034 Uiso 1 1 calc R U . . .
N7 N 0.3570(6) 0.8757(5) 0.2962(3) 0.0245(6) Uani 1 1 d . . . . .
N8 N 0.1968(6) 0.6099(4) 0.4056(3) 0.0232(7) Uani 1 1 d . . . . .
N9 N 0.1362(6) 0.7892(5) 0.4596(3) 0.0250(7) Uani 1 1 d . . . . .
N10 N 0.1116(7) 0.9629(5) 0.6554(3) 0.0317(9) Uani 1 1 d . . . . .
H10A H 0.062742 1.054952 0.632857 0.038 Uiso 1 1 calc R U . . .
H10B H 0.129651 0.970670 0.731306 0.038 Uiso 1 1 calc R U . . .
N11 N 0.3076(6) 0.3487(5) 0.4615(3) 0.0260(8) Uani 1 1 d . . . . .
H11A H 0.313514 0.284256 0.387055 0.031 Uiso 1 1 calc R U . . .
H11B H 0.339979 0.299340 0.518902 0.031 Uiso 1 1 calc R U . . .
N12 N 0.2830(6) 0.6186(5) 0.7053(3) 0.0268(7) Uani 1 1 d . . . . .
C1 C 0.2548(7) 0.6470(6) 0.1055(4) 0.0238(8) Uani 1 1 d . . . . .
C2 C 0.2278(7) 0.4499(6) 0.0484(4) 0.0250(9) Uani 1 1 d . . . . .
C3 C 0.2666(7) 0.6942(5) 0.2285(4) 0.0218(7) Uani 1 1 d . . . . .
C4 C 0.2215(7) 0.5581(5) 0.2860(4) 0.0248(8) Uani 1 1 d . . . . .
C5 C 0.2509(7) 0.5178(5) 0.4870(4) 0.0219(7) Uani 1 1 d . . . . .
C6 C 0.2294(7) 0.6450(6) 0.5968(4) 0.0242(7) Uani 1 1 d . . . . .
C7 C 0.1589(7) 0.8103(6) 0.5736(4) 0.0244(7) 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
O1 N7 1.239(5) . ?
O2 N7 1.217(5) . ?
O3 N12 1.230(5) . ?
O4 N12 1.255(5) . ?
N1 N2 1.346(5) . ?
N1 C2 1.327(5) . ?
N2 N3 1.301(6) . ?
N3 N4 1.342(5) . ?
N4 N5 1.350(5) . ?
N4 C2 1.360(6) . ?
N5 C4 1.312(5) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C1 1.313(6) . ?
N7 C3 1.439(5) . ?
N8 N9 1.416(5) . ?
N8 C4 1.386(5) . ?
N8 C5 1.375(6) . ?
N9 C7 1.305(6) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C7 1.346(5) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C5 1.308(5) . ?
N12 C6 1.373(6) . ?
C1 C2 1.436(5) . ?
C1 C3 1.389(6) . ?
C3 C4 1.430(6) . ?
C5 C6 1.398(5) . ?
C6 C7 1.444(6) . ?

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 N1 N2 105.6(4) . . ?
N3 N2 N1 112.0(3) . . ?
N2 N3 N4 106.0(4) . . ?
N3 N4 N5 123.6(4) . . ?
N3 N4 C2 108.3(3) . . ?
N5 N4 C2 127.8(3) . . ?
C4 N5 N4 112.6(4) . . ?
H6A N6 H6B 120.0 . . ?
C1 N6 H6A 120.0 . . ?
C1 N6 H6B 120.0 . . ?
O1 N7 C3 117.0(3) . . ?
O2 N7 O1 123.7(3) . . ?
O2 N7 C3 119.2(4) . . ?
C4 N8 N9 119.2(3) . . ?
C5 N8 N9 112.4(3) . . ?
C5 N8 C4 127.7(4) . . ?
C7 N9 N8 105.4(3) . . ?
H10A N10 H10B 120.0 . . ?
C7 N10 H10A 120.0 . . ?
C7 N10 H10B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
O3 N12 O4 121.7(4) . . ?
O3 N12 C6 119.9(4) . . ?
O4 N12 C6 118.4(3) . . ?
N6 C1 C2 118.3(4) . . ?
N6 C1 C3 128.6(4) . . ?
C3 C1 C2 113.0(4) . . ?
N1 C2 N4 108.1(4) . . ?
N1 C2 C1 132.4(4) . . ?
N4 C2 C1 119.3(4) . . ?
C1 C3 N7 117.3(4) . . ?
C1 C3 C4 121.1(3) . . ?
C4 C3 N7 120.8(4) . . ?
N5 C4 N8 114.1(4) . . ?
N5 C4 C3 124.7(4) . . ?
N8 C4 C3 121.1(3) . . ?
N8 C5 C6 104.3(4) . . ?
N11 C5 N8 125.4(4) . . ?
N11 C5 C6 130.3(4) . . ?
N12 C6 C5 124.9(4) . . ?
N12 C6 C7 127.7(4) . . ?
C5 C6 C7 107.2(4) . . ?
N9 C7 N10 123.3(4) . . ?
N9 C7 C6 110.6(3) . . ?
N10 C7 C6 126.0(4) . . ?

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 N7 C3 C1 38.7(6) . . . . ?
O1 N7 C3 C4 -151.5(4) . . . . ?
O2 N7 C3 C1 -137.5(4) . . . . ?
O2 N7 C3 C4 32.3(6) . . . . ?
O3 N12 C6 C5 175.7(4) . . . . ?
O3 N12 C6 C7 1.6(7) . . . . ?
O4 N12 C6 C5 -5.6(7) . . . . ?
O4 N12 C6 C7 -179.7(4) . . . . ?
N1 N2 N3 N4 0.9(6) . . . . ?
N2 N1 C2 N4 0.3(5) . . . . ?
N2 N1 C2 C1 175.6(5) . . . . ?
N2 N3 N4 N5 174.0(4) . . . . ?
N2 N3 N4 C2 -0.7(5) . . . . ?
N3 N4 N5 C4 176.5(4) . . . . ?
N3 N4 C2 N1 0.2(6) . . . . ?
N3 N4 C2 C1 -175.7(4) . . . . ?
N4 N5 C4 N8 178.0(4) . . . . ?
N4 N5 C4 C3 -0.3(7) . . . . ?
N5 N4 C2 N1 -174.1(4) . . . . ?
N5 N4 C2 C1 9.9(7) . . . . ?
N6 C1 C2 N1 4.1(8) . . . . ?
N6 C1 C2 N4 178.9(4) . . . . ?
N6 C1 C3 N7 -17.8(7) . . . . ?
N6 C1 C3 C4 172.4(5) . . . . ?
N7 C3 C4 N5 -159.1(4) . . . . ?
N7 C3 C4 N8 22.7(7) . . . . ?
N8 N9 C7 N10 -178.2(4) . . . . ?
N8 N9 C7 C6 -1.4(5) . . . . ?
N8 C5 C6 N12 -174.3(4) . . . . ?
N8 C5 C6 C7 0.8(5) . . . . ?
N9 N8 C4 N5 -152.9(4) . . . . ?
N9 N8 C4 C3 25.5(6) . . . . ?
N9 N8 C5 N11 178.1(4) . . . . ?
N9 N8 C5 C6 -1.7(5) . . . . ?
N11 C5 C6 N12 5.9(8) . . . . ?
N11 C5 C6 C7 -179.0(5) . . . . ?
N12 C6 C7 N9 175.3(4) . . . . ?
N12 C6 C7 N10 -8.0(8) . . . . ?
C1 C3 C4 N5 10.4(7) . . . . ?
C1 C3 C4 N8 -167.8(4) . . . . ?
C2 N1 N2 N3 -0.8(6) . . . . ?
C2 N4 N5 C4 -10.0(7) . . . . ?
C2 C1 C3 N7 159.9(4) . . . . ?
C2 C1 C3 C4 -9.9(6) . . . . ?
C3 C1 C2 N1 -173.9(5) . . . . ?
C3 C1 C2 N4 0.9(6) . . . . ?
C4 N8 N9 C7 -169.3(4) . . . . ?
C4 N8 C5 N11 -11.5(7) . . . . ?
C4 N8 C5 C6 168.7(4) . . . . ?
C5 N8 N9 C7 2.0(5) . . . . ?
C5 N8 C4 N5 37.3(7) . . . . ?
C5 N8 C4 C3 -144.3(4) . . . . ?
C5 C6 C7 N9 0.5(5) . . . . ?
C5 C6 C7 N10 177.1(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 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.565
