# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_Z-458101
_database_code_depnum_ccdc_archive 'CCDC 2288834'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-02-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 N4 O2'
_chemical_formula_sum            'C8 H4 N4 O2'
_chemical_formula_weight         188.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H4N4O2
_chemical_oxdiff_usercomment     Z458101
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                   7.74397(15)
_cell_length_b                   5.37413(10)
_cell_length_c                   18.7390(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.3886(18)
_cell_angle_gamma                90
_cell_volume                     769.42(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      76.5310
_cell_measurement_theta_min      5.7650
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.655
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0701
0 0 1 0.0678
1 0 0 0.0253
-1 0 0 0.0206
0 -1 0 0.1924
0 1 0 0.2435
1 0 -1 0.0395
-1 0 1 0.0206

_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 -0.0000 -0.9997 0.0811 0.0052 0.0186
-0.0002 0.0000 0.9997 -0.0811 -0.0052 -0.0186
0.9994 0.0004 0.0018 -0.0135 0.1524 -0.1312
-0.9994 -0.0004 -0.0018 0.0135 -0.1524 0.1312
-0.0005 -0.9995 0.0001 -0.0603 0.1794 0.2150
0.0005 0.9995 -0.0001 0.0603 -0.1794 -0.2150
0.9996 0.0004 -0.9979 0.0675 0.1576 -0.1127
-0.9996 -0.0004 0.9979 -0.0675 -0.1576 0.1127

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8675
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.623
_diffrn_reflns_theta_min         4.784
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  79.00   0.50    0.25    --  107.75-125.00   0.00   78
  2  ω     39.00 111.00   0.50    0.25    --  107.75-125.00-120.00  144
  3  ω    -62.00  24.00   0.50    0.08    --  -48.68  55.00   0.00  172
  4  ω    -51.00 -14.00   0.50    0.25    --  -86.25  45.00-180.00   74
  5  ω    -63.00 -14.00   0.50    0.25    --  -86.25  55.00   0.00   98
  6  ω     61.00  87.00   0.50    0.25    --  107.75-125.00  90.00   52
  7  ω     45.00  77.00   0.50    0.25    --  107.75-125.00 120.00   64
  8  ω     82.00 109.00   0.50    0.25    --  107.75-125.00 120.00   54
  9  ω     36.00 105.00   0.50    0.25    --  107.75 -95.00 -60.00  138
 10  ω     69.00  94.00   0.50    0.25    --  107.75 -95.00-120.00   50
 11  ω     42.00  67.00   0.50    0.25    --  107.75-125.00-180.00   50
 12  ω     36.00  62.00   0.50    0.25    --  107.75 -95.00-120.00   52
 13  ω     40.00  66.00   0.50    0.25    --  107.75 -83.00 -27.90   52
 14  ω    106.00 132.00   0.50    0.25    --  107.75 -83.00 -27.90   52
 15  ω     51.00  90.00   0.50    0.25    --  107.75 -77.00  30.00   78
 16  ω     38.00  64.00   0.50    0.25    --  107.75 -61.00 150.00   52
 17  ω     36.00  71.00   0.50    0.25    --  107.75 -61.00   0.00   70
 18  ω     40.00  71.00   0.50    0.25    --  107.75 -61.00-120.00   62
 19  ω     36.00  63.00   0.50    0.25    --  107.75 -55.00-142.00   54
 20  ω     36.00 166.00   0.50    0.25    --  107.75   0.00   0.00  260
 21  ω     97.00 178.00   0.50    0.25    --  107.75  45.00 -60.00  162
 22  ω     86.00 133.00   0.50    0.25    --  107.75  77.00   0.00   94
 23  ω     95.00 178.00   0.50    0.25    --  107.75  55.00   0.00  166
 24  ω    120.00 146.00   0.50    0.25    --  107.75  30.00 -30.00   52
 25  ω    110.00 136.00   0.50    0.25    --  107.75  30.00  90.00   52
 26  ω     97.00 146.00   0.50    0.25    --  107.75  45.00 120.00   98
 27  ω     36.00 120.00   0.50    0.08    --   48.68  55.00   0.00  168
 28  ω     96.00 128.00   0.50    0.25    --  107.75 125.00-120.00   64
 29  ω    -22.00  62.00   0.50    0.08    --   48.68 -55.00-142.00  168
 30  ω    137.00 176.00   0.50    0.25    --  107.75 125.00-120.00   78
 31  ω    -25.00  26.00   0.50    0.08    --   48.68 -19.00  30.00  102
 32  ω   -120.00 -35.00   0.50    0.08    --  -48.68 -55.00-142.00  170
 33  ω   -158.00 -73.00   0.50    0.25    --  -86.25 -55.00-142.00  170
 34  ω   -118.00 -73.00   0.50    0.08    --  -48.68-125.00-180.00   90
;
_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      -0.0134039000
_diffrn_orient_matrix_UB_12      0.0603290000
_diffrn_orient_matrix_UB_13      -0.0810875000
_diffrn_orient_matrix_UB_21      0.1525398000
_diffrn_orient_matrix_UB_22      -0.1796052000
_diffrn_orient_matrix_UB_23      -0.0051457000
_diffrn_orient_matrix_UB_31      -0.1311815000
_diffrn_orient_matrix_UB_32      -0.2150304000
_diffrn_orient_matrix_UB_33      -0.0185772000
_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                1531
_reflns_number_total             1627
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.041
_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)+(0.0603P)²+0.2643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O2 O 0.26178(12) 0.4976(2) 0.43414(5) 0.0338(3) Uani 1 1 d . . . . .
O6 O 0.72746(13) 0.69064(18) 0.24716(5) 0.0309(2) Uani 1 1 d . . . . .
N6 N 0.65238(13) 0.59950(19) 0.29517(5) 0.0241(2) Uani 1 1 d . . . . .
N5 N 0.50692(14) 0.70034(19) 0.30671(6) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.39296(14) 0.3183(2) 0.44626(6) 0.0294(3) Uani 1 1 d . . . . .
N3 N 0.28798(15) 0.6634(2) 0.38059(6) 0.0322(3) Uani 1 1 d . . . . .
C12 C 0.66038(15) 0.2681(2) 0.38824(6) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.73733(15) 0.3864(2) 0.33463(6) 0.0220(3) Uani 1 1 d . . . . .
C13 C 0.49771(16) 0.3750(2) 0.40074(6) 0.0234(3) Uani 1 1 d . . . . .
C11 C 0.74473(16) 0.0656(2) 0.42538(6) 0.0254(3) Uani 1 1 d . . . . .
H11 H 0.694269 -0.015851 0.462004 0.030 Uiso 1 1 calc R U . . .
C4 C 0.43318(16) 0.5864(2) 0.35996(7) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.89695(16) 0.3059(2) 0.31798(6) 0.0263(3) Uani 1 1 d . . . . .
H8 H 0.948767 0.387563 0.281782 0.032 Uiso 1 1 calc R U . . .
C10 C 0.90258(17) -0.0154(2) 0.40833(6) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.960033 -0.154328 0.433046 0.033 Uiso 1 1 calc R U . . .
C9 C 0.97821(16) 0.1053(3) 0.35508(7) 0.0281(3) Uani 1 1 d . . . . .
H9 H 1.087195 0.048402 0.344287 0.034 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
O2 N1 1.3918(15) . ?
O2 N3 1.3815(15) . ?
O6 N6 1.2483(13) . ?
N6 N5 1.2995(15) . ?
N6 C7 1.4603(15) . ?
N5 C4 1.3721(17) . ?
N1 C13 1.3056(16) . ?
N3 C4 1.3140(17) . ?
C12 C7 1.4014(16) . ?
C12 C13 1.4382(17) . ?
C12 C11 1.3954(17) . ?
C7 C8 1.3922(17) . ?
C13 C4 1.4141(17) . ?
C11 H11 0.9500 . ?
C11 C10 1.3831(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3778(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.3967(18) . ?
C9 H9 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
N3 O2 N1 112.05(9) . . ?
O6 N6 N5 118.34(10) . . ?
O6 N6 C7 116.64(10) . . ?
N5 N6 C7 125.02(10) . . ?
N6 N5 C4 114.20(10) . . ?
C13 N1 O2 104.26(10) . . ?
C4 N3 O2 104.17(10) . . ?
C7 C12 C13 114.93(11) . . ?
C11 C12 C7 119.49(11) . . ?
C11 C12 C13 125.57(11) . . ?
C12 C7 N6 120.65(11) . . ?
C8 C7 N6 118.25(11) . . ?
C8 C7 C12 121.10(11) . . ?
N1 C13 C12 131.84(12) . . ?
N1 C13 C4 109.77(11) . . ?
C4 C13 C12 118.35(11) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.31(12) . . ?
C10 C11 H11 120.3 . . ?
N5 C4 C13 126.81(11) . . ?
N3 C4 N5 123.44(12) . . ?
N3 C4 C13 109.75(11) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.63(11) . . ?
C9 C8 H8 120.7 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.55(12) . . ?
C9 C10 H10 119.7 . . ?
C8 C9 C10 120.92(11) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?

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
O2 N1 C13 C12 177.34(12) . . . . ?
O2 N1 C13 C4 -0.39(13) . . . . ?
O2 N3 C4 N5 179.80(10) . . . . ?
O2 N3 C4 C13 -0.40(13) . . . . ?
O6 N6 N5 C4 179.45(10) . . . . ?
O6 N6 C7 C12 -178.41(10) . . . . ?
O6 N6 C7 C8 2.14(16) . . . . ?
N6 N5 C4 N3 178.63(11) . . . . ?
N6 N5 C4 C13 -1.13(18) . . . . ?
N6 C7 C8 C9 179.84(10) . . . . ?
N5 N6 C7 C12 2.07(18) . . . . ?
N5 N6 C7 C8 -177.38(11) . . . . ?
N1 O2 N3 C4 0.17(13) . . . . ?
N1 C13 C4 N5 -179.68(11) . . . . ?
N1 C13 C4 N3 0.53(15) . . . . ?
N3 O2 N1 C13 0.15(13) . . . . ?
C12 C7 C8 C9 0.39(18) . . . . ?
C12 C13 C4 N5 2.24(19) . . . . ?
C12 C13 C4 N3 -177.55(10) . . . . ?
C12 C11 C10 C9 0.69(19) . . . . ?
C7 N6 N5 C4 -1.04(17) . . . . ?
C7 C12 C13 N1 -178.63(12) . . . . ?
C7 C12 C13 C4 -1.06(16) . . . . ?
C7 C12 C11 C10 -0.29(18) . . . . ?
C7 C8 C9 C10 0.01(18) . . . . ?
C13 C12 C7 N6 -0.83(16) . . . . ?
C13 C12 C7 C8 178.60(10) . . . . ?
C13 C12 C11 C10 -179.01(11) . . . . ?
C11 C12 C7 N6 -179.68(10) . . . . ?
C11 C12 C7 C8 -0.25(18) . . . . ?
C11 C12 C13 N1 0.1(2) . . . . ?
C11 C12 C13 C4 177.72(11) . . . . ?
C11 C10 C9 C8 -0.56(19) . . . . ?

_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.871
####################################################################### 
# 
# 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_Z461401
_database_code_depnum_ccdc_archive 'CCDC 2288835'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H3 N5 O4'
_chemical_formula_sum            'C8 H3 N5 O4'
_chemical_formula_weight         233.15
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H3N5O4
_chemical_oxdiff_usercomment     Z461401
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.2846(2)
_cell_length_b                   9.99780(10)
_cell_length_c                   6.38630(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     912.06(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5599
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      76.9440
_cell_measurement_theta_min      5.3760
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.551
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0120
-1 -1 0 0.0120
0 0 1 0.2971
0 0 -1 0.2484
0 1 0 0.0145
0 -1 0 0.0187
-1 1 0 0.0078
1 -1 0 0.0180

_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9984 0.9997 0.0001 0.0256 -0.1802 -0.0469
-0.9984 -0.9997 -0.0001 -0.0256 0.1802 0.0469
0.0003 -0.0007 0.9998 0.0429 -0.0537 0.2312
-0.0003 0.0007 -0.9998 -0.0429 0.0537 -0.2312
-0.0009 0.9990 -0.0002 0.1032 -0.1055 -0.0439
0.0009 -0.9990 0.0002 -0.1032 0.1055 0.0439
-1.0001 0.9983 -0.0004 0.1808 -0.0307 -0.0408
1.0001 -0.9983 0.0004 -0.1808 0.0307 0.0408

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6846
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.814
_diffrn_reflns_theta_min         5.401
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -64.00   0.50    1.00    --  -48.70-139.00  13.00  112
  2  ω   -122.00 -39.00   0.50    1.00    --  -48.70 -22.00  45.00  166
  3  ω    -28.00  26.00   0.50    1.00    --  -48.70  22.00-148.00  108
  4  ω   -156.00 -84.00   0.50    3.87    --  -86.25-103.00 -96.00  144
  5  ω    -90.00 -16.00   0.50    3.87    --  -86.25 131.00-100.00  148
  6  ω     38.00 116.00   0.50    3.87    --  107.75-131.00-171.00  156
  7  ω     97.00 178.00   0.50    3.87    --  107.75  22.00-148.00  162
  8  ω     46.00 121.00   0.50    3.87    --  107.75-139.00  13.00  150
  9  ω     71.00  97.00   0.50    3.87    --  107.75-103.00 -96.00   52
 10  ω    -22.00  25.00   0.50    1.00    --   48.70 -19.00 -90.00   94
 11  ω     37.00  71.00   0.50    3.87    --  107.75 -61.00  30.00   68
 12  ω     40.00  72.00   0.50    3.87    --  107.75-125.00 -30.00   64
 13  ω     49.00  75.00   0.50    3.87    --  107.75 -95.00  30.00   52
 14  ω     39.00  65.00   0.50    3.87    --  107.75-103.00 -34.16   52
 15  ω     36.00  69.00   0.50    3.87    --  107.75 -95.00  90.00   66
 16  ω    138.00 178.00   0.50    3.87    --  107.75  45.00 -60.00   80
 17  ω     83.00 109.00   0.50    3.87    --  107.75-125.00 -30.00   52
 18  ω     39.00  70.00   0.50    3.87    --  107.75 -61.00-150.00   62
 19  ω    147.00 177.00   0.50    3.87    --  107.75  30.00  90.00   60
 20  ω     41.00  69.00   0.50    3.87    --  107.75 -61.00 -30.00   56
 21  ω     69.00 106.00   0.50    3.87    --  107.75-103.00 -34.16   74
 22  ω     43.00  69.00   0.50    3.87    --  107.75-125.00   0.00   52
 23  ω     84.00 110.00   0.50    3.87    --  107.75-125.00  90.00   52
 24  ω    109.00 135.00   0.50    3.87    --  107.75  45.00  27.49   52
 25  ω     36.00  61.00   0.50    3.87    --  107.75 -61.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0776967000
_diffrn_orient_matrix_UB_12      0.1032424000
_diffrn_orient_matrix_UB_13      0.0430505000
_diffrn_orient_matrix_UB_21      -0.0747014000
_diffrn_orient_matrix_UB_22      -0.1056354000
_diffrn_orient_matrix_UB_23      -0.0537301000
_diffrn_orient_matrix_UB_31      -0.0030715000
_diffrn_orient_matrix_UB_32      -0.0438743000
_diffrn_orient_matrix_UB_33      0.2312489000
_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         0.389
_reflns_Friedel_fraction_full    0.507
_reflns_Friedel_fraction_max     0.468
_reflns_number_gt                1441
_reflns_number_total             1472
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1472
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.075
_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)+(0.0316P)²+0.2094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O2 O 0.61276(10) 0.88331(15) 0.6833(3) 0.0347(4) Uani 1 1 d . . . . .
O6 O 0.38947(9) 0.45745(13) 0.9105(2) 0.0253(3) Uani 1 1 d . . . . .
O15 O 0.16963(9) 0.36458(13) 0.3766(3) 0.0255(3) Uani 1 1 d . . . . .
O16 O 0.17178(10) 0.47825(14) 0.0886(3) 0.0321(4) Uani 1 1 d . . . . .
N1 N 0.54587(11) 0.86765(17) 0.5252(3) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.60246(11) 0.79113(18) 0.8420(3) 0.0323(4) Uani 1 1 d . . . . .
N5 N 0.49493(11) 0.61649(16) 0.9012(3) 0.0249(3) Uani 1 1 d . . . . .
N6 N 0.42463(10) 0.55456(15) 0.8153(3) 0.0210(3) Uani 1 1 d . . . . .
N14 N 0.19877(10) 0.45596(14) 0.2653(3) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.52949(12) 0.72054(18) 0.7831(3) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.38305(11) 0.59027(17) 0.6146(3) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.31014(11) 0.51031(17) 0.5430(3) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.287360 0.436729 0.622182 0.023 Uiso 1 1 calc R U . . .
C9 C 0.27276(11) 0.54349(17) 0.3514(3) 0.0192(4) Uani 1 1 d . . . . .
C10 C 0.30145(13) 0.65245(18) 0.2327(3) 0.0223(4) Uani 1 1 d . . . . .
H10 H 0.271862 0.672884 0.103332 0.027 Uiso 1 1 calc R U . . .
C11 C 0.37410(12) 0.73047(18) 0.3072(3) 0.0225(4) Uani 1 1 d . . . . .
H11 H 0.395160 0.805487 0.229000 0.027 Uiso 1 1 calc R U . . .
C12 C 0.41640(12) 0.69856(17) 0.4980(3) 0.0201(4) Uani 1 1 d . . . . .
C13 C 0.49534(12) 0.76687(17) 0.5902(3) 0.0218(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
O2 N1 1.399(2) . ?
O2 N3 1.378(3) . ?
O6 N6 1.251(2) . ?
O15 N14 1.230(2) . ?
O16 N14 1.213(2) . ?
N1 C13 1.307(2) . ?
N3 C4 1.314(2) . ?
N5 N6 1.301(2) . ?
N5 C4 1.377(3) . ?
N6 C7 1.457(2) . ?
N14 C9 1.478(2) . ?
C4 C13 1.404(3) . ?
C7 C8 1.390(2) . ?
C7 C12 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C12 C13 1.444(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
N3 O2 N1 112.52(13) . . ?
C13 N1 O2 103.56(17) . . ?
C4 N3 O2 103.50(17) . . ?
N6 N5 C4 113.92(17) . . ?
O6 N6 N5 118.31(16) . . ?
O6 N6 C7 117.01(15) . . ?
N5 N6 C7 124.68(16) . . ?
O15 N14 C9 117.80(15) . . ?
O16 N14 O15 124.52(16) . . ?
O16 N14 C9 117.68(15) . . ?
N3 C4 N5 122.25(19) . . ?
N3 C4 C13 110.47(18) . . ?
N5 C4 C13 127.28(17) . . ?
C8 C7 N6 116.98(16) . . ?
C8 C7 C12 121.72(17) . . ?
C12 C7 N6 121.29(16) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 C7 116.39(16) . . ?
C9 C8 H8 121.8 . . ?
C8 C9 N14 117.75(15) . . ?
C8 C9 C10 124.07(17) . . ?
C10 C9 N14 118.17(16) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.41(18) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.74(17) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C13 114.55(17) . . ?
C11 C12 C7 119.61(16) . . ?
C11 C12 C13 125.83(17) . . ?
N1 C13 C4 109.94(17) . . ?
N1 C13 C12 131.81(19) . . ?
C4 C13 C12 118.24(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
O2 N1 C13 C4 -0.05(19) . . . . ?
O2 N1 C13 C12 -178.56(18) . . . . ?
O2 N3 C4 N5 -179.61(17) . . . . ?
O2 N3 C4 C13 0.6(2) . . . . ?
O6 N6 C7 C8 -2.2(2) . . . . ?
O6 N6 C7 C12 178.94(15) . . . . ?
O15 N14 C9 C8 5.6(2) . . . . ?
O15 N14 C9 C10 -175.60(17) . . . . ?
O16 N14 C9 C8 -173.56(17) . . . . ?
O16 N14 C9 C10 5.3(2) . . . . ?
N1 O2 N3 C4 -0.6(2) . . . . ?
N3 O2 N1 C13 0.4(2) . . . . ?
N3 C4 C13 N1 -0.3(2) . . . . ?
N3 C4 C13 C12 178.40(16) . . . . ?
N5 N6 C7 C8 177.92(16) . . . . ?
N5 N6 C7 C12 -0.9(3) . . . . ?
N5 C4 C13 N1 179.84(17) . . . . ?
N5 C4 C13 C12 -1.4(3) . . . . ?
N6 N5 C4 N3 -177.55(17) . . . . ?
N6 N5 C4 C13 2.3(3) . . . . ?
N6 C7 C8 C9 -178.74(15) . . . . ?
N6 C7 C12 C11 -179.37(15) . . . . ?
N6 C7 C12 C13 1.7(2) . . . . ?
N14 C9 C10 C11 -176.56(16) . . . . ?
C4 N5 N6 O6 179.12(15) . . . . ?
C4 N5 N6 C7 -1.1(2) . . . . ?
C7 C8 C9 N14 176.62(15) . . . . ?
C7 C8 C9 C10 -2.2(3) . . . . ?
C7 C12 C13 N1 177.76(18) . . . . ?
C7 C12 C13 C4 -0.6(2) . . . . ?
C8 C7 C12 C11 1.9(3) . . . . ?
C8 C7 C12 C13 -177.06(16) . . . . ?
C8 C9 C10 C11 2.2(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C7 -1.8(3) . . . . ?
C10 C11 C12 C13 176.97(17) . . . . ?
C11 C12 C13 N1 -1.1(3) . . . . ?
C11 C12 C13 C4 -179.50(16) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.150
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_z461201
_database_code_depnum_ccdc_archive 'CCDC 2288836'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-06-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H3 N5 O4'
_chemical_formula_sum            'C8 H3 N5 O4'
_chemical_formula_weight         233.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H3 N5 O4'
_chemical_oxdiff_usercomment     Z461201
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.6598(2)
_cell_length_b                   12.7026(3)
_cell_length_c                   15.5750(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713.28(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7039
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      77.3860
_cell_measurement_theta_min      2.7580
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    1.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
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    1.808
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 -1 0.0565
0 -1 1 0.1113
0 1 -1 0.0297
1 -1 1 0.0741
-1 1 0 0.0460
1 -1 0 0.0646
0 0 -1 0.0191
0 0 1 0.0881
1 0 1 0.0658
0 1 1 0.0517
-1 -1 0 0.1771

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9992 0.9990 -1.0000 0.0114 -0.0782 0.2235
0.0003 -0.9995 0.9996 -0.0868 0.1123 -0.0661
-0.0003 0.9995 -0.9996 0.0868 -0.1123 0.0661
0.9998 -1.0000 0.9992 -0.1622 0.1464 0.0912
-0.9995 1.0002 0.0006 0.1824 -0.0503 -0.1026
0.9995 -1.0002 -0.0006 -0.1824 0.0503 0.1026
-0.0003 -0.0002 -0.9998 -0.0202 -0.0961 0.0113
0.0003 0.0002 0.9998 0.0202 0.0961 -0.0113
0.9997 -0.0003 0.9994 -0.0552 0.1302 0.1460
0.0002 0.9999 1.0000 0.1272 0.0800 0.0434
-0.9995 -0.9992 0.0002 -0.0316 -0.0179 -0.2121

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10416
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.670
_diffrn_reflns_theta_min         5.681
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -53.00   0.50    1.50    --  -48.70 -36.00-102.00  136
  2  ω    -97.00 -53.00   0.50    1.50    --  -48.70-154.00-121.00   88
  3  ω    -65.00 -15.00   0.50    1.50    --  -48.70  86.00-129.00  100
  4  ω    133.00 159.00   0.50    6.00    --  107.75  36.00  53.00   52
  5  ω    105.00 130.00   0.50    6.00    --  107.75  86.00-129.00   50
  6  ω     49.00  98.00   0.50    6.00    --  107.75 -86.00 112.00   98
  7  ω     61.00 106.00   0.50    6.00    --  107.75-121.00  36.00   90
  8  ω     35.00  93.00   0.50    1.50    --   48.70-125.00 -60.00  116
  9  ω     42.00  68.00   0.50    6.00    --  107.75 -61.00 150.00   52
 10  ω     36.00  69.00   0.50    6.00    --  107.75 -61.00-120.00   66
 11  ω    100.00 127.00   0.50    6.00    --  107.75 125.00 150.00   54
 12  ω    146.00 172.00   0.50    6.00    --  107.75 125.00 150.00   52
 13  ω     37.00  80.00   0.50    6.00    --  107.75 -77.00-180.00   86
 14  ω     40.00  65.00   0.50    6.00    --  107.75 -61.00 -90.00   50
 15  ω     98.00 132.00   0.50    6.00    --  107.75  45.00 150.00   68
 16  ω    143.00 178.00   0.50    6.00    --  107.75  45.00 150.00   70
 17  ω     70.00 100.00   0.50    6.00    --  107.75 -95.00  30.00   60
 18  ω     87.00 122.00   0.50    6.00    --  107.75  77.00  60.00   70
 19  ω    144.00 175.00   0.50    6.00    --  107.75  77.00  60.00   62
 20  ω     57.00  83.00   0.50    6.00    --  107.75 -77.00 120.00   52
 21  ω     44.00  70.00   0.50    6.00    --  107.75 -77.00  90.00   52
 22  ω     36.00  61.00   0.50    6.00    --  107.75 -61.00 -30.00   50
 23  ω     40.00  65.00   0.50    6.00    --  107.75-125.00   0.00   50
 24  ω     62.00  88.00   0.50    6.00    --  107.75 -77.00 150.00   52
 25  ω     72.00 102.00   0.50    6.00    --  107.75 -95.00 -90.00   60
 26  ω     99.00 150.00   0.50    6.00    --  107.75  45.00  30.00  102
 27  ω     36.00  61.00   0.50    6.00    --  107.75 -95.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0753862000
_diffrn_orient_matrix_UB_12      0.1070162000
_diffrn_orient_matrix_UB_13      0.0201907000
_diffrn_orient_matrix_UB_21      0.0341470000
_diffrn_orient_matrix_UB_22      -0.0162046000
_diffrn_orient_matrix_UB_23      0.0961463000
_diffrn_orient_matrix_UB_31      0.1574432000
_diffrn_orient_matrix_UB_32      0.0547864000
_diffrn_orient_matrix_UB_33      -0.0114003000
_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                1680
_reflns_number_total             1824
_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 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0042(6)
_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   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0439
_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)+(0.0858P)²+0.6883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.43278(13) 0.21109(9) 0.68702(7) 0.0202(3) Uani 1 1 d . . . . .
O2 O 0.89140(12) 0.51197(9) 0.66691(7) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.49707(13) 0.20447(8) 0.42780(7) 0.0201(3) Uani 1 1 d . . . . .
O4 O 0.35807(12) 0.33176(9) 0.37531(7) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.44527(15) 0.23989(10) 0.60133(8) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.53675(15) 0.26412(10) 0.73834(8) 0.0195(3) Uani 1 1 d . . . . .
N3 N 0.72531(14) 0.39366(10) 0.71128(8) 0.0179(3) Uani 1 1 d . . . . .
N4 N 0.78471(14) 0.44971(10) 0.64949(8) 0.0153(3) Uani 1 1 d . . . . .
N5 N 0.47046(14) 0.29776(10) 0.41421(8) 0.0147(3) Uani 1 1 d . . . . .
C1 C 0.61138(17) 0.32573(12) 0.68499(9) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.73581(15) 0.44497(11) 0.55950(9) 0.0140(3) Uani 1 1 d . . . . .
C3 C 0.80497(17) 0.51499(11) 0.50234(10) 0.0160(3) Uani 1 1 d . . . . .
H3 H 0.880(3) 0.5634(19) 0.5225(15) 0.029(5) Uiso 1 1 d . . . . .
C4 C 0.76135(16) 0.51357(11) 0.41712(10) 0.0165(3) Uani 1 1 d . . . . .
H4 H 0.806(2) 0.5627(18) 0.3741(15) 0.025(5) Uiso 1 1 d . . . . .
C5 C 0.64914(16) 0.44294(11) 0.38764(9) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.622(2) 0.4417(17) 0.3278(14) 0.023(5) Uiso 1 1 d . . . . .
C6 C 0.58393(15) 0.37424(11) 0.44571(9) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.62310(16) 0.37275(11) 0.53293(9) 0.0138(3) Uani 1 1 d . . . . .
C8 C 0.55576(16) 0.31000(11) 0.60051(9) 0.0150(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
O1 N1 1.3880(16) . ?
O1 N2 1.3796(17) . ?
O2 N4 1.2461(16) . ?
O3 N5 1.2256(17) . ?
O4 N5 1.2251(17) . ?
N1 C8 1.307(2) . ?
N2 C1 1.312(2) . ?
N3 N4 1.3029(18) . ?
N3 C1 1.373(2) . ?
N4 C2 1.4654(17) . ?
N5 C6 1.4664(18) . ?
C1 C8 1.415(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.402(2) . ?
C3 H3 0.95(2) . ?
C3 C4 1.380(2) . ?
C4 H4 0.99(2) . ?
C4 C5 1.400(2) . ?
C5 H5 0.96(2) . ?
C5 C6 1.378(2) . ?
C6 C7 1.4002(19) . ?
C7 C8 1.4433(19) . ?

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
N2 O1 N1 112.18(10) . . ?
C8 N1 O1 104.24(11) . . ?
C1 N2 O1 104.23(12) . . ?
N4 N3 C1 114.00(12) . . ?
O2 N4 N3 118.60(12) . . ?
O2 N4 C2 116.66(12) . . ?
N3 N4 C2 124.74(12) . . ?
O3 N5 C6 117.18(12) . . ?
O4 N5 O3 125.15(12) . . ?
O4 N5 C6 117.66(12) . . ?
N2 C1 N3 122.68(13) . . ?
N2 C1 C8 109.69(13) . . ?
N3 C1 C8 127.62(13) . . ?
C3 C2 N4 117.43(13) . . ?
C3 C2 C7 121.88(13) . . ?
C7 C2 N4 120.69(13) . . ?
C2 C3 H3 119.8(14) . . ?
C4 C3 C2 119.24(13) . . ?
C4 C3 H3 121.0(14) . . ?
C3 C4 H4 122.1(13) . . ?
C3 C4 C5 120.91(14) . . ?
C5 C4 H4 116.9(13) . . ?
C4 C5 H5 119.8(13) . . ?
C6 C5 C4 118.36(13) . . ?
C6 C5 H5 121.8(13) . . ?
C5 C6 N5 118.33(13) . . ?
C5 C6 C7 123.10(13) . . ?
C7 C6 N5 118.55(12) . . ?
C2 C7 C8 115.30(13) . . ?
C6 C7 C2 116.49(13) . . ?
C6 C7 C8 128.11(13) . . ?
N1 C8 C1 109.65(13) . . ?
N1 C8 C7 132.77(13) . . ?
C1 C8 C7 117.55(13) . . ?

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 C8 C1 -0.45(15) . . . . ?
O1 N1 C8 C7 -178.17(15) . . . . ?
O1 N2 C1 N3 179.09(12) . . . . ?
O1 N2 C1 C8 -0.89(15) . . . . ?
O2 N4 C2 C3 -4.18(18) . . . . ?
O2 N4 C2 C7 176.15(12) . . . . ?
O3 N5 C6 C5 123.47(14) . . . . ?
O3 N5 C6 C7 -55.33(17) . . . . ?
O4 N5 C6 C5 -55.41(17) . . . . ?
O4 N5 C6 C7 125.79(14) . . . . ?
N1 O1 N2 C1 0.63(15) . . . . ?
N2 O1 N1 C8 -0.10(15) . . . . ?
N2 C1 C8 N1 0.89(17) . . . . ?
N2 C1 C8 C7 179.01(12) . . . . ?
N3 N4 C2 C3 176.15(13) . . . . ?
N3 N4 C2 C7 -3.5(2) . . . . ?
N3 C1 C8 N1 -179.08(14) . . . . ?
N3 C1 C8 C7 -1.0(2) . . . . ?
N4 N3 C1 N2 -178.98(13) . . . . ?
N4 N3 C1 C8 1.0(2) . . . . ?
N4 C2 C3 C4 -179.54(12) . . . . ?
N4 C2 C7 C6 179.93(11) . . . . ?
N4 C2 C7 C8 3.27(19) . . . . ?
N5 C6 C7 C2 177.94(11) . . . . ?
N5 C6 C7 C8 -5.9(2) . . . . ?
C1 N3 N4 O2 -178.43(12) . . . . ?
C1 N3 N4 C2 1.24(19) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C7 C8 N1 176.32(15) . . . . ?
C2 C7 C8 C1 -1.26(19) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C3 C2 C7 C8 -176.39(12) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 N5 -177.85(12) . . . . ?
C4 C5 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C2 -0.8(2) . . . . ?
C5 C6 C7 C8 175.37(13) . . . . ?
C6 C7 C8 N1 0.1(3) . . . . ?
C6 C7 C8 C1 -177.47(13) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.773
_oxdiff_exptl_absorpt_empirical_full_min 0.327
####################################################################### 
# 
# 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_z456301
_database_code_depnum_ccdc_archive 'CCDC 2288837'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-01-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H3 N5 O5'
_chemical_formula_sum            'C8 H3 N5 O5'
_chemical_formula_weight         249.15
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H3N5O5
_chemical_oxdiff_usercomment     Z456301
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   14.40027(12)
_cell_length_b                   10.46252(9)
_cell_length_c                   6.13809(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     924.783(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    99.98(15)
_cell_measurement_theta_max      77.0910
_cell_measurement_theta_min      5.2140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11803
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.688
_diffrn_reflns_theta_min         5.226
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -14.00   0.50    0.36    --  -86.25  83.00  31.00  194
  2  ω    -44.00 -14.00   0.50    0.36    --  -86.25  39.00-117.00   60
  3  ω    -44.00  23.00   0.50    0.09    --  -48.70  39.00-117.00  134
  4  ω     68.00  94.00   0.50    0.36    --  107.75-153.00-136.00   52
  5  ω     82.00 107.00   0.50    0.36    --  107.75-125.00-120.00   50
  6  ω     39.00  72.00   0.50    0.36    --  107.75-108.00-105.53   66
  7  ω     39.00  72.00   0.50    0.36    --  107.75-125.00-120.00   66
  8  ω     82.00 107.00   0.50    0.36    --  107.75 -83.00 -89.00   50
  9  ω     79.00 104.00   0.50    0.36    --  107.75-108.00-105.53   50
 10  ω     46.00  89.00   0.50    0.36    --  107.75-125.00   0.00   86
 11  ω     50.00  75.00   0.50    0.36    --  107.75-121.00  23.00   50
 12  ω     56.00 103.00   0.50    0.36    --  107.75-107.00 169.67   94
 13  ω    -23.00  44.00   0.50    0.09    --   48.70 -39.00  88.00  134
 14  ω     43.00  76.00   0.50    0.36    --  107.75 -77.00 120.00   66
 15  ω     42.00  89.00   0.50    0.36    --  107.75 -77.00  30.00   94
 16  ω     45.00  83.00   0.50    0.36    --  107.75 -69.00 176.30   76
 17  ω     38.00  91.00   0.50    0.36    --  107.75 -77.00   0.00  106
 18  ω     49.00  82.00   0.50    0.36    --  107.75 -77.00 -30.00   66
 19  ω     43.00  71.00   0.50    0.36    --  107.75 -61.00  30.00   56
 20  ω     37.00  63.00   0.50    0.36    --  107.75 -61.00  90.00   52
 21  ω     36.00  69.00   0.50    0.36    --  107.75 -61.00 -30.00   66
 22  ω     36.00  70.00   0.50    0.36    --  107.75 -61.00 -60.00   68
 23  ω     36.00  61.00   0.50    0.36    --  107.75 -61.00-120.00   50
 24  ω     45.00  71.00   0.50    0.36    --  107.75 -77.00-180.00   52
 25  ω     38.00  71.00   0.50    0.36    --  107.75 -61.00  60.00   66
 26  ω    127.00 153.00   0.50    0.36    --  107.75  30.00   0.00   52
 27  ω    100.00 133.00   0.50    0.36    --  107.75  45.00 -60.00   66
 28  ω     97.00 178.00   0.50    0.36    --  107.75  39.00-117.00  162
 29  ω    153.00 178.00   0.50    0.36    --  107.75  45.00 -60.00   50
 30  ω    107.00 153.00   0.50    0.36    --  107.75  45.00  30.00   92
 31  ω     97.00 122.00   0.50    0.36    --  107.75  30.00 150.00   50
 32  ω    130.00 178.00   0.50    0.36    --  107.75  30.00 150.00   96
 33  ω    117.00 155.00   0.50    0.36    --  107.75  83.00  31.00   76
 34  ω    137.00 163.00   0.50    0.36    --  107.75 125.00 -60.00   52
 35  ω     76.00 158.00   0.50    0.36    --  107.75 153.00 -94.00  164
 36  ω     99.00 125.00   0.50    0.36    --  107.75 125.00 -60.00   52
 37  ω    124.00 149.00   0.50    0.36    --  107.75 121.00 105.00   50
 38  ω   -158.00 -75.00   0.50    0.36    --  -86.25 -39.00  88.00  166
 39  ω   -121.00 -39.00   0.50    0.09    --  -48.70 -39.00  88.00  164
 40  ω   -158.00 -79.00   0.50    0.36    --  -86.25 -83.00 -89.00  158
 41  ω   -120.00 -54.00   0.50    0.09    --  -48.70-153.00-136.00  132
 42  ω   -146.00 -54.00   0.50    0.36    --  -86.25-153.00-136.00  184
;
_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      0.0456779000
_diffrn_orient_matrix_UB_12      0.1128969000
_diffrn_orient_matrix_UB_13      -0.1201207000
_diffrn_orient_matrix_UB_21      0.0960193000
_diffrn_orient_matrix_UB_22      -0.0624762000
_diffrn_orient_matrix_UB_23      0.0305903000
_diffrn_orient_matrix_UB_31      -0.0117275000
_diffrn_orient_matrix_UB_32      -0.0709415000
_diffrn_orient_matrix_UB_33      -0.2182532000
_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         0.586
_reflns_Friedel_fraction_full    0.714
_reflns_Friedel_fraction_max     0.711
_reflns_number_gt                1703
_reflns_number_total             1716
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(14)
_refine_ls_extinction_coef       0.0069(12)
_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   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.077
_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)+(0.0584P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0831
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.18002(10) 0.35191(13) 0.3693(3) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.42567(10) 0.55042(15) 0.8283(3) 0.0181(4) Uani 1 1 d . . . . .
C1 C 0.38104(13) 0.58334(18) 0.6232(3) 0.0168(4) Uani 1 1 d . . . . .
O2 O 0.17568(10) 0.46462(13) 0.0723(3) 0.0224(4) Uani 1 1 d . . . . .
N2 N 0.49351(12) 0.61445(16) 0.9163(3) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.31146(12) 0.50239(18) 0.5477(4) 0.0169(4) Uani 1 1 d . . . . .
H2 H 0.292258 0.429472 0.628181 0.020 Uiso 1 1 calc R U . . .
N3 N 0.59680(12) 0.78491(17) 0.8552(4) 0.0264(4) Uani 1 1 d . . . . .
O3 O 0.39541(10) 0.45423(13) 0.9270(3) 0.0224(4) Uani 1 1 d . . . . .
C3 C 0.27189(12) 0.53327(16) 0.3508(4) 0.0163(4) Uani 1 1 d . . . . .
O4 O 0.60720(10) 0.87584(14) 0.6952(3) 0.0267(4) Uani 1 1 d . . . . .
N4 N 0.53413(11) 0.85724(16) 0.5299(3) 0.0212(4) Uani 1 1 d . . . . .
C4 C 0.29469(13) 0.64242(17) 0.2311(4) 0.0183(4) Uani 1 1 d . . . . .
H4 H 0.263125 0.661938 0.099363 0.022 Uiso 1 1 calc R U . . .
N5 N 0.20386(11) 0.44380(15) 0.2572(3) 0.0171(4) Uani 1 1 d . . . . .
O5 O 0.53335(10) 0.92822(15) 0.3721(3) 0.0289(4) Uani 1 1 d . . . . .
C5 C 0.36419(13) 0.72143(18) 0.3087(3) 0.0185(4) Uani 1 1 d . . . . .
H5 H 0.381380 0.795912 0.229892 0.022 Uiso 1 1 calc R U . . .
C6 C 0.40899(13) 0.69087(18) 0.5040(4) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.48521(13) 0.75818(18) 0.5986(4) 0.0186(4) Uani 1 1 d . . . . .
C8 C 0.52438(13) 0.71711(18) 0.7958(4) 0.0197(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
O1 N5 1.231(2) . ?
N1 C1 1.455(3) . ?
N1 N2 1.302(3) . ?
N1 O3 1.253(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.401(3) . ?
O2 N5 1.224(3) . ?
N2 C8 1.378(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
N3 O4 1.375(3) . ?
N3 C8 1.313(3) . ?
C3 C4 1.397(3) . ?
C3 N5 1.472(2) . ?
O4 N4 1.475(2) . ?
N4 O5 1.221(3) . ?
N4 C7 1.322(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(3) . ?
C6 C7 1.427(3) . ?
C7 C8 1.403(3) . ?

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
N2 N1 C1 124.65(17) . . ?
O3 N1 C1 117.07(16) . . ?
O3 N1 N2 118.28(18) . . ?
C2 C1 N1 117.53(17) . . ?
C2 C1 C6 121.45(18) . . ?
C6 C1 N1 121.00(17) . . ?
N1 N2 C8 114.89(18) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.64(18) . . ?
C3 C2 H2 121.7 . . ?
C8 N3 O4 105.20(19) . . ?
C2 C3 C4 123.84(18) . . ?
C2 C3 N5 118.01(16) . . ?
C4 C3 N5 118.12(18) . . ?
N3 O4 N4 108.80(14) . . ?
O5 N4 O4 118.18(16) . . ?
O5 N4 C7 136.48(19) . . ?
C7 N4 O4 105.32(17) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
O1 N5 C3 117.64(17) . . ?
O2 N5 O1 124.37(17) . . ?
O2 N5 C3 117.98(17) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.50(18) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 113.87(18) . . ?
C5 C6 C1 119.92(18) . . ?
C5 C6 C7 126.19(18) . . ?
N4 C7 C6 131.8(2) . . ?
N4 C7 C8 107.52(18) . . ?
C8 C7 C6 120.59(18) . . ?
N2 C8 C7 124.89(18) . . ?
N3 C8 N2 121.9(2) . . ?
N3 C8 C7 113.2(2) . . ?

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 C1 C2 C3 -178.30(16) . . . . ?
N1 C1 C6 C5 -179.18(16) . . . . ?
N1 C1 C6 C7 2.3(2) . . . . ?
N1 N2 C8 N3 -174.78(18) . . . . ?
N1 N2 C8 C7 3.4(3) . . . . ?
C1 N1 N2 C8 -2.2(3) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
C1 C2 C3 N5 174.83(16) . . . . ?
C1 C6 C7 N4 175.2(2) . . . . ?
C1 C6 C7 C8 -1.3(2) . . . . ?
N2 N1 C1 C2 177.86(17) . . . . ?
N2 N1 C1 C6 -0.6(3) . . . . ?
C2 C1 C6 C5 2.5(3) . . . . ?
C2 C1 C6 C7 -176.08(17) . . . . ?
C2 C3 C4 C5 3.3(3) . . . . ?
C2 C3 N5 O1 6.3(2) . . . . ?
C2 C3 N5 O2 -172.77(16) . . . . ?
N3 O4 N4 O5 -178.67(18) . . . . ?
N3 O4 N4 C7 -0.1(2) . . . . ?
O3 N1 C1 C2 -3.0(2) . . . . ?
O3 N1 C1 C6 178.63(16) . . . . ?
O3 N1 N2 C8 178.58(16) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
O4 N3 C8 N2 178.87(17) . . . . ?
O4 N3 C8 C7 0.5(2) . . . . ?
O4 N4 C7 C6 -176.43(18) . . . . ?
O4 N4 C7 C8 0.4(2) . . . . ?
N4 C7 C8 N2 -178.90(18) . . . . ?
N4 C7 C8 N3 -0.6(2) . . . . ?
C4 C3 N5 O1 -175.73(17) . . . . ?
C4 C3 N5 O2 5.2(3) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C4 C5 C6 C7 176.12(18) . . . . ?
N5 C3 C4 C5 -174.59(16) . . . . ?
O5 N4 C7 C6 1.7(4) . . . . ?
O5 N4 C7 C8 178.6(2) . . . . ?
C5 C6 C7 N4 -3.2(3) . . . . ?
C5 C6 C7 C8 -179.69(18) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C7 C8 N2 -1.6(3) . . . . ?
C6 C7 C8 N3 176.64(18) . . . . ?
C8 N3 O4 N4 -0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.361
####################################################################### 
# 
# 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_z0231
_database_code_depnum_ccdc_archive 'CCDC 2288838'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-08-15 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-01-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 N4 O3'
_chemical_formula_sum            'C8 H4 N4 O3'
_chemical_formula_weight         204.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H4N4O3
_chemical_oxdiff_usercomment     Z0231
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                   8.09790(10)
_cell_length_b                   15.91000(10)
_cell_length_c                   18.71190(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.2870(10)
_cell_angle_gamma                90
_cell_volume                     2400.54(4)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    24861
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      77.2940
_cell_measurement_theta_min      3.6320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32530
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.866
_diffrn_reflns_theta_min         3.653
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -73.00   0.50    0.15    --  -48.70-125.00 -90.00   90
  2  ω   -116.00 -78.00   0.50    0.15    --  -48.70-125.00   0.00   76
  3  ω   -158.00 -79.00   0.50    0.45    --  -86.25 -78.00 117.00  158
  4  ω   -121.00 -39.00   0.50    0.15    --  -48.70 -38.00 -60.00  164
  5  ω   -108.00 -14.00   0.50    0.45    --  -86.25  78.00-118.00  188
  6  ω    -71.00  24.00   0.50    0.15    --  -48.70  78.00-118.00  190
  7  ω     68.00 101.00   0.50    0.45    --  107.75 -95.00-150.00   66
  8  ω     74.00 107.00   0.50    0.45    --  107.75-110.00-172.60   66
  9  ω     63.00 127.00   0.50    0.45    --  107.75-147.00-163.59  128
 10  ω     76.00 103.00   0.50    0.45    --  107.75 -95.00 -90.00   54
 11  ω     40.00  65.00   0.50    0.45    --  107.75-125.00 -30.00   50
 12  ω     39.00  74.00   0.50    0.45    --  107.75-103.00 -55.62   70
 13  ω     56.00  82.00   0.50    0.45    --  107.75 -95.00   0.00   52
 14  ω     40.00 110.00   0.50    0.45    --  107.75-125.00  30.00  140
 15  ω     40.00 111.00   0.50    0.45    --  107.75-125.00  90.00  142
 16  ω     41.00 101.00   0.50    0.45    --  107.75 -95.00 120.00  120
 17  ω     36.00  66.00   0.50    0.45    --  107.75 -61.00  60.00   60
 18  ω     36.00 100.00   0.50    0.45    --  107.75 -78.00 117.00  128
 19  ω    -21.00  71.00   0.50    0.15    --   48.70 -78.00 117.00  184
 20  ω     36.00  64.00   0.50    0.45    --  107.75 -61.00 150.00   56
 21  ω     45.00  70.00   0.50    0.45    --  107.75 -61.00 -60.00   50
 22  ω     51.00  77.00   0.50    0.45    --  107.75 -77.00-120.00   52
 23  ω     37.00  71.00   0.50    0.45    --  107.75 -61.00-150.00   68
 24  ω     37.00  65.00   0.50    0.45    --  107.75 -77.00-180.00   56
 25  ω     56.00  82.00   0.50    0.45    --  107.75 -76.00-178.96   52
 26  ω     45.00  71.00   0.50    0.45    --  107.75 -61.00-180.00   52
 27  ω    101.00 174.00   0.50    0.45    --  107.75  78.00-118.00  146
 28  ω     86.00 154.00   0.50    0.45    --  107.75  77.00 -90.00  136
 29  ω    130.00 171.00   0.50    0.45    --  107.75  72.00 -19.10   82
 30  ω    109.00 172.00   0.50    0.45    --  107.75  72.00 -36.27  126
 31  ω     99.00 125.00   0.50    0.45    --  107.75  72.00 -19.10   52
 32  ω    114.00 151.00   0.50    0.45    --  107.75  77.00   0.00   74
 33  ω    103.00 136.00   0.50    0.45    --  107.75  45.00 150.00   66
 34  ω    151.00 177.00   0.50    0.45    --  107.75  15.00 120.00   52
 35  ω    120.00 147.00   0.50    0.45    --  107.75  30.00  60.00   54
 36  ω    122.00 148.00   0.50    0.45    --  107.75  15.00 120.00   52
 37  ω    108.00 155.00   0.50    0.45    --  107.75  45.00   0.00   94
 38  ω    146.00 176.00   0.50    0.45    --  107.75  15.00-150.00   60
 39  ω    150.00 176.00   0.50    0.45    --  107.75  45.00-180.00   52
 40  ω     99.00 125.00   0.50    0.45    --  107.75  45.00-180.00   52
 41  ω    119.00 176.00   0.50    0.45    --  107.75 125.00-180.00  114
 42  ω    111.00 170.00   0.50    0.45    --  107.75 125.00  60.00  118
 43  ω    122.00 154.00   0.50    0.45    --  107.75 125.00 120.00   64
;
_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      -0.0773423000
_diffrn_orient_matrix_UB_12      -0.0820853000
_diffrn_orient_matrix_UB_13      -0.0313091000
_diffrn_orient_matrix_UB_21      0.1220750000
_diffrn_orient_matrix_UB_22      0.0006123000
_diffrn_orient_matrix_UB_23      -0.0584484000
_diffrn_orient_matrix_UB_31      0.1250306000
_diffrn_orient_matrix_UB_32      -0.0513564000
_diffrn_orient_matrix_UB_33      0.0493710000
_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                4842
_reflns_number_total             5114
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.034
_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)+(0.0553P)²+0.8672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C2B(H2B), C2C(H2C), C3A(H3A), C3B(H3B), C3C(H3C), C4A(H4A),
 C4B(H4B), C4C(H4C), C5A(H5A), C5B(H5B), C5C(H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O1A O 0.76014(11) 0.40196(6) 0.27011(5) 0.0295(2) Uani 1 1 d . . . . .
O1B O 0.78687(10) 0.06955(5) 0.23172(4) 0.02443(19) Uani 1 1 d . . . . .
O1C O 0.25841(11) 0.23785(5) 0.26497(5) 0.02593(19) Uani 1 1 d . . . . .
O2A O 0.21070(10) 0.46335(6) 0.41878(5) 0.0271(2) Uani 1 1 d . . . . .
O2B O 0.25510(10) 0.10122(5) 0.39658(5) 0.02563(19) Uani 1 1 d . . . . .
O2C O 0.77020(10) 0.29871(6) 0.09436(5) 0.02625(19) Uani 1 1 d . . . . .
O3A O 0.29994(11) 0.58582(6) 0.47713(5) 0.0287(2) Uani 1 1 d . . . . .
O3B O 0.35180(11) 0.21267(6) 0.46823(4) 0.02653(19) Uani 1 1 d . . . . .
O3C O 0.65562(11) 0.41137(6) 0.02911(5) 0.0294(2) Uani 1 1 d . . . . .
N1A N 0.66352(12) 0.43366(6) 0.31073(5) 0.0224(2) Uani 1 1 d . . . . .
N1B N 0.69559(12) 0.09280(6) 0.27822(5) 0.0197(2) Uani 1 1 d . . . . .
N1C N 0.34431(12) 0.26874(6) 0.21950(5) 0.0198(2) Uani 1 1 d . . . . .
N2A N 0.52282(13) 0.39597(6) 0.31733(6) 0.0244(2) Uani 1 1 d . . . . .
N2B N 0.55345(12) 0.05537(6) 0.28068(5) 0.0210(2) Uani 1 1 d . . . . .
N2C N 0.48798(12) 0.23507(6) 0.21204(5) 0.0210(2) Uani 1 1 d . . . . .
N3A N 0.27434(13) 0.40696(7) 0.37273(6) 0.0267(2) Uani 1 1 d . . . . .
N3B N 0.31222(13) 0.05412(7) 0.34191(6) 0.0250(2) Uani 1 1 d . . . . .
N3C N 0.72339(13) 0.24638(7) 0.14770(5) 0.0247(2) Uani 1 1 d . . . . .
N4A N 0.33371(12) 0.52951(6) 0.43545(5) 0.0228(2) Uani 1 1 d . . . . .
N4B N 0.38017(12) 0.16425(6) 0.41923(5) 0.0214(2) Uani 1 1 d . . . . .
N4C N 0.63668(12) 0.35941(6) 0.07650(5) 0.0224(2) Uani 1 1 d . . . . .
C1A C 0.71857(14) 0.51109(7) 0.34819(6) 0.0208(2) Uani 1 1 d . . . . .
C1B C 0.75840(14) 0.16038(7) 0.32627(6) 0.0189(2) Uani 1 1 d . . . . .
C1C C 0.27270(14) 0.33973(7) 0.17800(6) 0.0198(2) Uani 1 1 d . . . . .
C2A C 0.87296(15) 0.54335(8) 0.33636(6) 0.0242(2) Uani 1 1 d . . . . .
H2A H 0.940835 0.515944 0.304735 0.029 Uiso 1 1 calc R U . . .
C2B C 0.91641(14) 0.19132(7) 0.31944(6) 0.0219(2) Uani 1 1 d . . . . .
H2B H 0.982648 0.168878 0.284683 0.026 Uiso 1 1 calc R U . . .
C2C C 0.11649(14) 0.36806(8) 0.19166(6) 0.0239(2) Uani 1 1 d . . . . .
H2C H 0.059174 0.343068 0.228312 0.029 Uiso 1 1 calc R U . . .
C3A C 0.92597(15) 0.61645(8) 0.37171(7) 0.0260(3) Uani 1 1 d . . . . .
H3A H 1.031117 0.639478 0.364038 0.031 Uiso 1 1 calc R U . . .
C3B C 0.97511(14) 0.25594(7) 0.36473(6) 0.0232(2) Uani 1 1 d . . . . .
H3B H 1.083348 0.277607 0.361135 0.028 Uiso 1 1 calc R U . . .
C3C C 0.04606(15) 0.43359(8) 0.15068(7) 0.0265(3) Uani 1 1 d . . . . .
H3C H -0.060262 0.454099 0.159650 0.032 Uiso 1 1 calc R U . . .
C4A C 0.82659(15) 0.65668(7) 0.41851(6) 0.0242(2) Uani 1 1 d . . . . .
H4A H 0.865283 0.706424 0.442649 0.029 Uiso 1 1 calc R U . . .
C4B C 0.87772(14) 0.28958(7) 0.41545(6) 0.0230(2) Uani 1 1 d . . . . .
H4B H 0.919713 0.334323 0.445463 0.028 Uiso 1 1 calc R U . . .
C4C C 0.12953(16) 0.46985(8) 0.09634(7) 0.0264(3) Uani 1 1 d . . . . .
H4C H 0.078466 0.514004 0.068158 0.032 Uiso 1 1 calc R U . . .
C5A C 0.67226(14) 0.62465(7) 0.42999(6) 0.0221(2) Uani 1 1 d . . . . .
H5A H 0.604895 0.652161 0.461767 0.026 Uiso 1 1 calc R U . . .
C5B C 0.72054(14) 0.25836(7) 0.42242(6) 0.0212(2) Uani 1 1 d . . . . .
H5B H 0.654561 0.281161 0.457124 0.025 Uiso 1 1 calc R U . . .
C5C C 0.28611(15) 0.44211(7) 0.08307(6) 0.0236(2) Uani 1 1 d . . . . .
H5C H 0.342694 0.467132 0.046210 0.028 Uiso 1 1 calc R U . . .
C6A C 0.61681(14) 0.55139(7) 0.39427(6) 0.0199(2) Uani 1 1 d . . . . .
C6B C 0.66038(13) 0.19287(7) 0.37771(6) 0.0190(2) Uani 1 1 d . . . . .
C6C C 0.35940(14) 0.37696(7) 0.12460(6) 0.0199(2) Uani 1 1 d . . . . .
C7A C 0.46082(14) 0.51070(7) 0.39959(6) 0.0205(2) Uani 1 1 d . . . . .
C7B C 0.50302(14) 0.15255(7) 0.37893(6) 0.0196(2) Uani 1 1 d . . . . .
C7C C 0.51986(14) 0.34143(7) 0.11860(6) 0.0199(2) Uani 1 1 d . . . . .
C8A C 0.42202(14) 0.43597(7) 0.36169(6) 0.0217(2) Uani 1 1 d . . . . .
C8B C 0.45850(14) 0.08575(7) 0.33197(6) 0.0205(2) Uani 1 1 d . . . . .
C8C C 0.57578(14) 0.27296(7) 0.16158(6) 0.0200(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
O1A N1A 1.2465(13) . ?
O1B N1B 1.2485(13) . ?
O1C N1C 1.2483(13) . ?
O2A N3A 1.3765(14) . ?
O2A N4A 1.4630(12) . ?
O2B N3B 1.3817(13) . ?
O2B N4B 1.4602(12) . ?
O2C N3C 1.3794(13) . ?
O2C N4C 1.4652(13) . ?
O3A N4A 1.2349(14) . ?
O3B N4B 1.2352(13) . ?
O3C N4C 1.2323(13) . ?
N1A N2A 1.3035(14) . ?
N1A C1A 1.4663(14) . ?
N1B N2B 1.3005(13) . ?
N1B C1B 1.4626(14) . ?
N1C N2C 1.3000(14) . ?
N1C C1C 1.4601(14) . ?
N2A C8A 1.3730(16) . ?
N2B C8B 1.3719(15) . ?
N2C C8C 1.3726(15) . ?
N3A C8A 1.3158(16) . ?
N3B C8B 1.3159(15) . ?
N3C C8C 1.3162(15) . ?
N4A C7A 1.3140(15) . ?
N4B C7B 1.3157(15) . ?
N4C C7C 1.3170(15) . ?
C1A C2A 1.3881(16) . ?
C1A C6A 1.4015(16) . ?
C1B C2B 1.3879(15) . ?
C1B C6B 1.4016(16) . ?
C1C C2C 1.3887(16) . ?
C1C C6C 1.4041(16) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3863(17) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.3880(16) . ?
C2C H2C 0.9500 . ?
C2C C3C 1.3856(17) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3978(18) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.3955(17) . ?
C3C H3C 0.9500 . ?
C3C C4C 1.3965(19) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3846(16) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.3837(16) . ?
C4C H4C 0.9500 . ?
C4C C5C 1.3864(17) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3971(16) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3957(15) . ?
C5C H5C 0.9500 . ?
C5C C6C 1.3947(16) . ?
C6A C7A 1.4310(15) . ?
C6B C7B 1.4287(15) . ?
C6C C7C 1.4309(15) . ?
C7A C8A 1.4051(16) . ?
C7B C8B 1.4047(16) . ?
C7C C8C 1.4042(16) . ?

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
N3A O2A N4A 108.39(8) . . ?
N3B O2B N4B 108.47(8) . . ?
N3C O2C N4C 108.46(8) . . ?
O1A N1A N2A 118.35(10) . . ?
O1A N1A C1A 116.82(10) . . ?
N2A N1A C1A 124.83(10) . . ?
O1B N1B N2B 118.15(9) . . ?
O1B N1B C1B 116.85(9) . . ?
N2B N1B C1B 125.00(9) . . ?
O1C N1C N2C 118.13(9) . . ?
O1C N1C C1C 116.62(9) . . ?
N2C N1C C1C 125.25(9) . . ?
N1A N2A C8A 114.68(10) . . ?
N1B N2B C8B 114.73(9) . . ?
N1C N2C C8C 114.73(9) . . ?
C8A N3A O2A 105.53(9) . . ?
C8B N3B O2B 105.33(9) . . ?
C8C N3C O2C 105.31(9) . . ?
O3A N4A O2A 118.07(9) . . ?
O3A N4A C7A 135.82(10) . . ?
C7A N4A O2A 106.10(9) . . ?
O3B N4B O2B 118.18(9) . . ?
O3B N4B C7B 135.72(10) . . ?
C7B N4B O2B 106.10(9) . . ?
O3C N4C O2C 117.91(9) . . ?
O3C N4C C7C 136.06(11) . . ?
C7C N4C O2C 106.03(9) . . ?
C2A C1A N1A 118.24(10) . . ?
C2A C1A C6A 121.21(11) . . ?
C6A C1A N1A 120.55(10) . . ?
C2B C1B N1B 118.39(10) . . ?
C2B C1B C6B 121.18(10) . . ?
C6B C1B N1B 120.43(10) . . ?
C2C C1C N1C 118.49(10) . . ?
C2C C1C C6C 121.18(10) . . ?
C6C C1C N1C 120.31(10) . . ?
C1A C2A H2A 120.7 . . ?
C3A C2A C1A 118.55(11) . . ?
C3A C2A H2A 120.7 . . ?
C1B C2B H2B 120.9 . . ?
C1B C2B C3B 118.25(11) . . ?
C3B C2B H2B 120.9 . . ?
C1C C2C H2C 120.7 . . ?
C3C C2C C1C 118.55(11) . . ?
C3C C2C H2C 120.7 . . ?
C2A C3A H3A 119.6 . . ?
C2A C3A C4A 120.81(11) . . ?
C4A C3A H3A 119.6 . . ?
C2B C3B H3B 119.5 . . ?
C2B C3B C4B 121.07(11) . . ?
C4B C3B H3B 119.5 . . ?
C2C C3C H3C 119.6 . . ?
C2C C3C C4C 120.77(11) . . ?
C4C C3C H3C 119.6 . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A C3A 120.57(11) . . ?
C5A C4A H4A 119.7 . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B C3B 120.59(11) . . ?
C5B C4B H4B 119.7 . . ?
C3C C4C H4C 119.6 . . ?
C5C C4C C3C 120.73(11) . . ?
C5C C4C H4C 119.6 . . ?
C4A C5A H5A 120.4 . . ?
C4A C5A C6A 119.19(11) . . ?
C6A C5A H5A 120.4 . . ?
C4B C5B H5B 120.5 . . ?
C4B C5B C6B 119.00(11) . . ?
C6B C5B H5B 120.5 . . ?
C4C C5C H5C 120.5 . . ?
C4C C5C C6C 119.08(11) . . ?
C6C C5C H5C 120.5 . . ?
C1A C6A C7A 114.12(10) . . ?
C5A C6A C1A 119.65(10) . . ?
C5A C6A C7A 126.23(11) . . ?
C1B C6B C7B 114.06(10) . . ?
C5B C6B C1B 119.90(10) . . ?
C5B C6B C7B 126.03(11) . . ?
C1C C6C C7C 113.97(10) . . ?
C5C C6C C1C 119.67(11) . . ?
C5C C6C C7C 126.36(11) . . ?
N4A C7A C6A 132.11(11) . . ?
N4A C7A C8A 107.53(10) . . ?
C8A C7A C6A 120.36(11) . . ?
N4B C7B C6B 131.92(11) . . ?
N4B C7B C8B 107.55(10) . . ?
C8B C7B C6B 120.51(10) . . ?
N4C C7C C6C 131.96(11) . . ?
N4C C7C C8C 107.43(10) . . ?
C8C C7C C6C 120.59(10) . . ?
N2A C8A C7A 125.43(11) . . ?
N3A C8A N2A 122.13(11) . . ?
N3A C8A C7A 112.44(11) . . ?
N2B C8B C7B 125.18(10) . . ?
N3B C8B N2B 122.28(10) . . ?
N3B C8B C7B 112.55(11) . . ?
N2C C8C C7C 125.07(10) . . ?
N3C C8C N2C 122.15(10) . . ?
N3C C8C C7C 112.77(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
O1A N1A N2A C8A -178.52(9) . . . . ?
O1A N1A C1A C2A -0.29(15) . . . . ?
O1A N1A C1A C6A 179.29(10) . . . . ?
O1B N1B N2B C8B -178.46(9) . . . . ?
O1B N1B C1B C2B -2.89(14) . . . . ?
O1B N1B C1B C6B 176.95(10) . . . . ?
O1C N1C N2C C8C -179.39(9) . . . . ?
O1C N1C C1C C2C 0.20(15) . . . . ?
O1C N1C C1C C6C -178.53(10) . . . . ?
O2A N3A C8A N2A -179.33(10) . . . . ?
O2A N3A C8A C7A 0.35(13) . . . . ?
O2A N4A C7A C6A 179.89(11) . . . . ?
O2A N4A C7A C8A -0.09(12) . . . . ?
O2B N3B C8B N2B -179.20(9) . . . . ?
O2B N3B C8B C7B 0.60(13) . . . . ?
O2B N4B C7B C6B -177.80(11) . . . . ?
O2B N4B C7B C8B 0.61(12) . . . . ?
O2C N3C C8C N2C 179.37(9) . . . . ?
O2C N3C C8C C7C 0.65(13) . . . . ?
O2C N4C C7C C6C -178.06(11) . . . . ?
O2C N4C C7C C8C 0.28(12) . . . . ?
O3A N4A C7A C6A -1.0(2) . . . . ?
O3A N4A C7A C8A 179.06(12) . . . . ?
O3B N4B C7B C6B 1.5(2) . . . . ?
O3B N4B C7B C8B 179.93(12) . . . . ?
O3C N4C C7C C6C 1.3(2) . . . . ?
O3C N4C C7C C8C 179.67(12) . . . . ?
N1A N2A C8A N3A 178.48(10) . . . . ?
N1A N2A C8A C7A -1.16(17) . . . . ?
N1A C1A C2A C3A -179.87(10) . . . . ?
N1A C1A C6A C5A 179.38(10) . . . . ?
N1A C1A C6A C7A -0.54(15) . . . . ?
N1B N2B C8B N3B -179.26(10) . . . . ?
N1B N2B C8B C7B 0.97(16) . . . . ?
N1B C1B C2B C3B 179.47(10) . . . . ?
N1B C1B C6B C5B -178.88(10) . . . . ?
N1B C1B C6B C7B 1.76(14) . . . . ?
N1C N2C C8C N3C 179.95(10) . . . . ?
N1C N2C C8C C7C -1.49(16) . . . . ?
N1C C1C C2C C3C -177.88(10) . . . . ?
N1C C1C C6C C5C 176.97(10) . . . . ?
N1C C1C C6C C7C -2.60(15) . . . . ?
N2A N1A C1A C2A 179.22(10) . . . . ?
N2A N1A C1A C6A -1.19(16) . . . . ?
N2B N1B C1B C2B 176.76(10) . . . . ?
N2B N1B C1B C6B -3.39(16) . . . . ?
N2C N1C C1C C2C 179.24(10) . . . . ?
N2C N1C C1C C6C 0.50(16) . . . . ?
N3A O2A N4A O3A -179.02(9) . . . . ?
N3A O2A N4A C7A 0.31(11) . . . . ?
N3B O2B N4B O3B -179.74(9) . . . . ?
N3B O2B N4B C7B -0.28(11) . . . . ?
N3C O2C N4C O3C -179.42(9) . . . . ?
N3C O2C N4C C7C 0.10(11) . . . . ?
N4A O2A N3A C8A -0.40(11) . . . . ?
N4A C7A C8A N2A 179.51(11) . . . . ?
N4A C7A C8A N3A -0.16(14) . . . . ?
N4B O2B N3B C8B -0.20(12) . . . . ?
N4B C7B C8B N2B 178.99(10) . . . . ?
N4B C7B C8B N3B -0.80(14) . . . . ?
N4C O2C N3C C8C -0.45(11) . . . . ?
N4C C7C C8C N2C -179.29(10) . . . . ?
N4C C7C C8C N3C -0.61(13) . . . . ?
C1A N1A N2A C8A 1.97(16) . . . . ?
C1A C2A C3A C4A 0.28(17) . . . . ?
C1A C6A C7A N4A -178.71(11) . . . . ?
C1A C6A C7A C8A 1.27(15) . . . . ?
C1B N1B N2B C8B 1.89(15) . . . . ?
C1B C2B C3B C4B -0.55(17) . . . . ?
C1B C6B C7B N4B 179.04(11) . . . . ?
C1B C6B C7B C8B 0.80(15) . . . . ?
C1C N1C N2C C8C 1.59(15) . . . . ?
C1C C2C C3C C4C 0.61(18) . . . . ?
C1C C6C C7C N4C -179.15(11) . . . . ?
C1C C6C C7C C8C 2.70(15) . . . . ?
C2A C1A C6A C5A -1.05(17) . . . . ?
C2A C1A C6A C7A 179.04(10) . . . . ?
C2A C3A C4A C5A -0.60(18) . . . . ?
C2B C1B C6B C5B 0.96(16) . . . . ?
C2B C1B C6B C7B -178.40(10) . . . . ?
C2B C3B C4B C5B 0.88(18) . . . . ?
C2C C1C C6C C5C -1.73(16) . . . . ?
C2C C1C C6C C7C 178.70(10) . . . . ?
C2C C3C C4C C5C -1.21(18) . . . . ?
C3A C4A C5A C6A 0.09(17) . . . . ?
C3B C4B C5B C6B -0.28(17) . . . . ?
C3C C4C C5C C6C 0.31(18) . . . . ?
C4A C5A C6A C1A 0.71(16) . . . . ?
C4A C5A C6A C7A -179.39(10) . . . . ?
C4B C5B C6B C1B -0.62(16) . . . . ?
C4B C5B C6B C7B 178.66(10) . . . . ?
C4C C5C C6C C1C 1.13(17) . . . . ?
C4C C5C C6C C7C -179.36(11) . . . . ?
C5A C6A C7A N4A 1.4(2) . . . . ?
C5A C6A C7A C8A -178.64(11) . . . . ?
C5B C6B C7B N4B -0.3(2) . . . . ?
C5B C6B C7B C8B -178.51(11) . . . . ?
C5C C6C C7C N4C 1.3(2) . . . . ?
C5C C6C C7C C8C -176.84(11) . . . . ?
C6A C1A C2A C3A 0.55(17) . . . . ?
C6A C7A C8A N2A -0.48(17) . . . . ?
C6A C7A C8A N3A 179.85(10) . . . . ?
C6B C1B C2B C3B -0.37(17) . . . . ?
C6B C7B C8B N2B -2.38(17) . . . . ?
C6B C7B C8B N3B 177.83(10) . . . . ?
C6C C1C C2C C3C 0.85(17) . . . . ?
C6C C7C C8C N2C -0.72(17) . . . . ?
C6C C7C C8C N3C 177.95(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.935
_oxdiff_exptl_absorpt_empirical_full_min 0.694
####################################################################### 
# 
# 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_Z461504
_database_code_depnum_ccdc_archive 'CCDC 2295832'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_audit_creation_date             2023-09-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
# start Validation Reply Form
_vrf_PLAT089_Z461504             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.38 Note  
RESPONSE: The small size and weak reflectivity of the crystal do not 
allow the use of Mo-radiation. More reflections on Cu-radiation cannot be 
obtained.
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H2 N6 O6'
_chemical_formula_sum            'C8 H2 N6 O6'
_chemical_formula_weight         278.16
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H2N6O6
_chemical_oxdiff_usercomment     Z461504
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   12.53304(19)
_cell_length_b                   8.30693(13)
_cell_length_c                   9.61288(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1000.81(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9012
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      78.3880
_cell_measurement_theta_min      3.5270
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.783
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.0266
-1 1 0 0.0171
-1 -1 0 0.0162
1 1 0 0.0145
0 0 -1 0.0847
0 0 1 0.0950
-1 0 0 0.0217
1 0 0 0.0235

_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9988 -1.0000 -0.0012 0.0200 -0.2208 0.0189
-0.9988 1.0000 0.0012 -0.0200 0.2208 -0.0189
-1.0001 -1.0003 0.0005 0.1932 -0.0621 0.0912
1.0001 1.0003 -0.0005 -0.1932 0.0621 -0.0912
-0.0007 -0.0001 -1.0003 -0.0668 0.0063 0.1456
0.0007 0.0001 1.0003 0.0668 -0.0063 -0.1456
-0.9995 -0.0002 0.0008 0.0866 0.0793 0.0361
0.9995 0.0002 -0.0008 -0.0866 -0.0793 -0.0361

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.794
_diffrn_reflns_theta_min         5.325
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  28.00   0.50    1.50    --  -46.94  33.00  74.00  132
  2  ω   -121.00 -32.00   0.50    1.50    --  -46.94 -33.00 -84.00  178
  3  ω      8.00  82.00   0.50    1.50    --   46.94-102.00  75.00  148
  4  ω   -166.00 -77.00   0.50    6.00    --  -91.75 -33.00 -84.00  178
  5  ω    -80.00 -21.00   0.50    6.00    --  -91.75 101.00 -85.00  118
  6  ω   -163.00 -85.00   0.50    6.00    --  -91.75-102.00  75.00  156
  7  ω     42.00 106.00   0.50    6.00    --  113.25-102.00  75.00  128
  8  ω    107.00 178.00   0.50    6.00    --  113.25 101.00 -85.00  142
  9  ω    106.00 178.00   0.50    6.00    --  113.25 102.00 178.00  144
 10  ω     42.00 106.00   0.50    6.00    --  113.25-101.00 170.00  128
 11  ω     99.00 178.00   0.50    6.00    --  113.25  33.00  74.00  158
 12  ω    -81.00  14.00   0.50    1.50    --  -46.94 102.00 178.00  190
 13  ω    -26.00  25.00   0.50    1.50    --   46.94 -19.00 150.00  102
 14  ω    137.00 163.00   0.50    6.00    --  113.25  77.00-120.00   52
 15  ω     96.00 141.00   0.50    6.00    --  113.25 125.00-120.00   90
 16  ω     43.00  79.00   0.50    6.00    --  113.25-125.00  60.00   72
 17  ω     83.00 109.00   0.50    6.00    --  113.25-125.00  60.00   52
 18  ω     81.00 106.00   0.50    6.00    --  113.25 -95.00  90.00   50
 19  ω     41.00  67.00   0.50    6.00    --  113.25 -61.00  30.00   52
 20  ω     43.00  97.00   0.50    6.00    --  113.25 -77.00 -60.00  108
 21  ω     42.00  89.00   0.50    6.00    --  113.25 -77.00 -30.00   94
 22  ω     78.00 111.00   0.50    6.00    --  113.25-125.00-150.00   66
 23  ω    140.00 166.00   0.50    6.00    --  113.25  15.00-180.00   52
 24  ω     43.00  69.00   0.50    6.00    --  113.25 -77.00-180.00   52
 25  ω     65.00 103.00   0.50    6.00    --  113.25 -77.00-120.00   76
 26  ω     41.00  69.00   0.50    6.00    --  113.25 -95.00  90.00   56
 27  ω     41.00  68.00   0.50    6.00    --  113.25 -61.00 150.00   54
 28  ω     42.00  71.00   0.50    6.00    --  113.25 -61.00  90.00   58
 29  ω     70.00 106.00   0.50    6.00    --  113.25-125.00-120.00   72
 30  ω     74.00 108.00   0.50    6.00    --  113.25-125.00  30.00   68
 31  ω    107.00 133.00   0.50    6.00    --  113.25  45.00-150.00   52
 32  ω     49.00  75.00   0.50    6.00    --  113.25 -77.00-150.00   52
 33  ω     62.00 103.00   0.50    6.00    --  113.25 -77.00 -90.00   82
 34  ω     49.00 100.00   0.50    6.00    --  113.25 -77.00  90.00  102
 35  ω     91.00 138.00   0.50    6.00    --  113.25   0.00-180.00   94
 36  ω    151.00 177.00   0.50    6.00    --  113.25  90.00 -43.37   52
 37  ω    105.00 175.00   0.50    6.00    --  113.25  45.00-120.00  140
 38  ω    104.00 174.00   0.50    6.00    --  113.25  45.00-153.54  140
 39  ω     93.00 175.00   0.50    6.00    --  113.25  77.00 120.00  164
 40  ω     68.00 111.00   0.50    6.00    --  113.25 -82.00-162.92   86
 41  ω     42.00  71.00   0.50    6.00    --  113.25 -61.00-150.00   58
;
_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      -0.0865604000
_diffrn_orient_matrix_UB_12      -0.1065404000
_diffrn_orient_matrix_UB_13      0.0668261000
_diffrn_orient_matrix_UB_21      -0.0794001000
_diffrn_orient_matrix_UB_22      0.1414677000
_diffrn_orient_matrix_UB_23      -0.0062789000
_diffrn_orient_matrix_UB_31      -0.0362754000
_diffrn_orient_matrix_UB_32      -0.0549599000
_diffrn_orient_matrix_UB_33      -0.1455292000
_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         0.643
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.728
_reflns_number_gt                1884
_reflns_number_total             1908
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.50
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_coef       0.0032(7)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.057
_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)+(0.0485P)²+0.4434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.38264(15) 0.4257(2) 0.7343(2) 0.0270(4) Uani 1 1 d . . . . .
O5 O 0.71603(16) 0.8181(2) 0.5790(3) 0.0382(5) Uani 1 1 d . . . . .
O15 O 0.83546(17) 0.4227(2) 0.4247(3) 0.0441(6) Uani 1 1 d . . . . .
O16 O 0.78813(18) 0.2542(3) 0.2640(3) 0.0444(6) Uani 1 1 d . . . . .
O18 O 0.52334(16) -0.1339(2) 0.3752(2) 0.0329(5) Uani 1 1 d . . . . .
O19 O 0.39536(17) -0.0718(2) 0.5177(3) 0.0380(5) Uani 1 1 d . . . . .
N1 N 0.46735(17) 0.4782(3) 0.6834(2) 0.0241(5) Uani 1 1 d . . . . .
N2 N 0.4994(2) 0.6210(3) 0.7180(3) 0.0304(5) Uani 1 1 d . . . . .
N4 N 0.62916(19) 0.8147(3) 0.6691(3) 0.0359(6) Uani 1 1 d . . . . .
N6 N 0.73033(19) 0.6744(3) 0.5104(3) 0.0338(6) Uani 1 1 d . . . . .
N14 N 0.77204(18) 0.3286(3) 0.3709(3) 0.0303(5) Uani 1 1 d . . . . .
N17 N 0.47873(17) -0.0418(3) 0.4565(3) 0.0276(5) Uani 1 1 d . . . . .
C3 C 0.5905(2) 0.6693(3) 0.6515(3) 0.0287(6) Uani 1 1 d . . . . .
C7 C 0.6534(2) 0.5808(3) 0.5550(3) 0.0268(6) Uani 1 1 d . . . . .
C8 C 0.6209(2) 0.4166(3) 0.5251(3) 0.0234(5) Uani 1 1 d . . . . .
C9 C 0.67032(19) 0.2986(3) 0.4421(3) 0.0246(5) Uani 1 1 d . . . . .
C10 C 0.6257(2) 0.1494(3) 0.4189(3) 0.0253(5) Uani 1 1 d . . . . .
H10 H 0.660006 0.072598 0.360961 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5296(2) 0.1151(3) 0.4827(3) 0.0231(5) Uani 1 1 d . . . . .
C12 C 0.4774(2) 0.2218(3) 0.5681(3) 0.0228(5) Uani 1 1 d . . . . .
H12 H 0.411776 0.194420 0.611507 0.027 Uiso 1 1 calc R U . . .
C13 C 0.52434(19) 0.3710(3) 0.5883(3) 0.0220(5) 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 1.248(3) . ?
O5 N4 1.392(4) . ?
O5 N6 1.375(3) . ?
O15 N14 1.229(4) . ?
O16 N14 1.216(4) . ?
O18 N17 1.228(3) . ?
O19 N17 1.225(3) . ?
N1 N2 1.296(3) . ?
N1 C13 1.462(3) . ?
N2 C3 1.368(4) . ?
N4 C3 1.313(4) . ?
N6 C7 1.310(4) . ?
N14 C9 1.468(3) . ?
N17 C11 1.473(3) . ?
C3 C7 1.422(4) . ?
C7 C8 1.452(3) . ?
C8 C9 1.407(4) . ?
C8 C13 1.406(3) . ?
C9 C10 1.378(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(4) . ?
C11 C12 1.374(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?

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
N6 O5 N4 112.5(2) . . ?
O1 N1 N2 118.9(2) . . ?
O1 N1 C13 116.6(2) . . ?
N2 N1 C13 124.5(2) . . ?
N1 N2 C3 114.0(2) . . ?
C3 N4 O5 103.1(2) . . ?
C7 N6 O5 105.2(2) . . ?
O15 N14 C9 118.2(3) . . ?
O16 N14 O15 124.9(2) . . ?
O16 N14 C9 116.9(2) . . ?
O18 N17 C11 117.6(2) . . ?
O19 N17 O18 124.6(2) . . ?
O19 N17 C11 117.9(2) . . ?
N2 C3 C7 128.0(2) . . ?
N4 C3 N2 121.1(3) . . ?
N4 C3 C7 110.8(3) . . ?
N6 C7 C3 108.3(2) . . ?
N6 C7 C8 134.4(3) . . ?
C3 C7 C8 117.3(2) . . ?
C9 C8 C7 130.0(2) . . ?
C13 C8 C7 114.2(2) . . ?
C13 C8 C9 115.9(2) . . ?
C8 C9 N14 121.9(2) . . ?
C10 C9 N14 115.4(2) . . ?
C10 C9 C8 122.7(2) . . ?
C9 C10 H10 121.1 . . ?
C9 C10 C11 117.9(2) . . ?
C11 C10 H10 121.1 . . ?
C10 C11 N17 119.0(2) . . ?
C12 C11 N17 117.9(2) . . ?
C12 C11 C10 123.2(2) . . ?
C11 C12 H12 121.3 . . ?
C11 C12 C13 117.3(2) . . ?
C13 C12 H12 121.3 . . ?
C8 C13 N1 121.8(2) . . ?
C12 C13 N1 115.1(2) . . ?
C12 C13 C8 123.1(2) . . ?

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 N2 C3 -177.2(2) . . . . ?
O1 N1 C13 C8 -179.7(2) . . . . ?
O1 N1 C13 C12 -1.0(3) . . . . ?
O5 N4 C3 N2 -176.6(3) . . . . ?
O5 N4 C3 C7 1.6(3) . . . . ?
O5 N6 C7 C3 0.5(3) . . . . ?
O5 N6 C7 C8 179.2(3) . . . . ?
O15 N14 C9 C8 30.1(4) . . . . ?
O15 N14 C9 C10 -151.6(3) . . . . ?
O16 N14 C9 C8 -151.7(3) . . . . ?
O16 N14 C9 C10 26.6(4) . . . . ?
O18 N17 C11 C10 -2.0(4) . . . . ?
O18 N17 C11 C12 176.8(2) . . . . ?
O19 N17 C11 C10 177.6(3) . . . . ?
O19 N17 C11 C12 -3.6(4) . . . . ?
N1 N2 C3 N4 175.8(3) . . . . ?
N1 N2 C3 C7 -2.0(4) . . . . ?
N2 N1 C13 C8 -0.2(4) . . . . ?
N2 N1 C13 C12 178.5(3) . . . . ?
N2 C3 C7 N6 176.6(3) . . . . ?
N2 C3 C7 C8 -2.4(4) . . . . ?
N4 O5 N6 C7 0.5(3) . . . . ?
N4 C3 C7 N6 -1.4(3) . . . . ?
N4 C3 C7 C8 179.6(2) . . . . ?
N6 O5 N4 C3 -1.3(3) . . . . ?
N6 C7 C8 C9 5.7(5) . . . . ?
N6 C7 C8 C13 -173.4(3) . . . . ?
N14 C9 C10 C11 -179.6(2) . . . . ?
N17 C11 C12 C13 -178.0(2) . . . . ?
C3 C7 C8 C9 -175.7(3) . . . . ?
C3 C7 C8 C13 5.2(3) . . . . ?
C7 C8 C9 N14 1.5(4) . . . . ?
C7 C8 C9 C10 -176.7(3) . . . . ?
C7 C8 C13 N1 -4.2(3) . . . . ?
C7 C8 C13 C12 177.2(2) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C9 C8 C13 N1 176.5(2) . . . . ?
C9 C8 C13 C12 -2.1(4) . . . . ?
C9 C10 C11 N17 178.3(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 N1 -178.2(2) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C13 N1 N2 C3 3.3(4) . . . . ?
C13 C8 C9 N14 -179.4(2) . . . . ?
C13 C8 C9 C10 2.4(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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.865
