# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

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

data_5-PGV-2062
_database_code_depnum_ccdc_archive 'CCDC 2308196'
loop_
_audit_author_name
_audit_author_address
'Aida I Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT430_5-PGV-2062          
;
PROBLEM: Short Inter D...A Contact  O5       ..O5       .       2.81 Ang.  
RESPONSE: These intermolecular interactions are expected for this structure.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N11 O8'
_chemical_formula_sum            'C7 H7 N11 O8'
_chemical_formula_weight         373.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H12N6O12
_chemical_oxdiff_usercomment     PGV-2062
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.67654(7)
_cell_length_b                   15.58666(16)
_cell_length_c                   10.82025(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.3532(9)
_cell_angle_gamma                90
_cell_volume                     1286.71(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14190
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.2920
_cell_measurement_theta_min      4.9940
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (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            colorless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0437
0 1 0 0.0475
0 0 -1 0.0231
0 0 1 0.0194
-1 1 -1 0.0407
1 -1 1 0.0338
-1 -1 -1 0.0552
1 1 1 0.0382

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 -0.9999 0.0002 0.0069 -0.0986 0.0034
0.0003 0.9999 -0.0002 -0.0069 0.0986 -0.0034
-0.0006 0.0001 -0.9997 0.1377 0.0108 0.0378
0.0006 -0.0001 0.9997 -0.1377 -0.0108 -0.0378
-1.0003 0.9998 -0.9996 0.2056 0.1084 -0.1531
1.0003 -0.9998 0.9996 -0.2056 -0.1084 0.1531
-1.0008 -0.9999 -0.9993 0.2195 -0.0887 -0.1464
1.0008 0.9999 0.9993 -0.2195 0.0887 0.1464

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.670
_diffrn_reflns_theta_min         4.996
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -70.00   0.50    0.40    --  -46.46-131.00  58.00   94
  2  ω   -119.00 -64.00   0.50    0.40    --  -46.46-139.00-116.00  110
  3  ω     42.00 103.00   0.50    0.40    --   46.46-139.00-116.00  122
  4  ω     38.00  97.00   0.50    0.40    --   46.46-131.00  58.00  118
  5  ω   -158.00 -64.00   0.50    1.60    --  -91.75-139.00-116.00  188
  6  ω    -91.00 -21.00   0.50    1.60    --  -91.75 131.00 129.00  140
  7  ω     42.00 122.00   0.50    1.60    --  113.25-139.00-116.00  160
  8  ω     42.00 116.00   0.50    1.60    --  113.25-131.00  58.00  148
  9  ω     91.00 178.00   0.50    1.60    --  113.25 131.00 129.00  174
 10  ω    -27.00  29.00   0.50    0.40    --  -46.46  19.00 -30.00  112
 11  ω    -27.00  29.00   0.50    0.40    --  -46.46  19.00  90.00  112
 12  ω    -90.00 -16.00   0.50    0.40    --  -46.46 131.00 129.00  148
 13  ω    -29.00  27.00   0.50    0.40    --   46.46 -19.00 -60.00  112
 14  ω    -51.00 -19.00   0.50    1.60    --  -91.75  45.00 -60.00   64
 15  ω     41.00 105.00   0.50    1.60    --  113.25 -77.00  30.00  128
 16  ω     41.00 105.00   0.50    1.60    --  113.25 -77.00-150.00  128
 17  ω     41.00  71.00   0.50    1.60    --  113.25 -61.00  90.00   60
 18  ω     41.00 106.00   0.50    1.60    --  113.25 -95.00  90.00  130
 19  ω     43.00 111.00   0.50    1.60    --  113.25-125.00 -60.00  136
 20  ω    115.00 169.00   0.50    1.60    --  113.25  30.00  60.00  108
 21  ω     52.00  78.00   0.50    1.60    --  113.25 -77.00  60.00   52
 22  ω     80.00 106.00   0.50    1.60    --  113.25-125.00-180.00   52
 23  ω    102.00 133.00   0.50    1.60    --  113.25 125.00-150.00   62
 24  ω     99.00 158.00   0.50    1.60    --  113.25  30.00 120.00  118
 25  ω     45.00  94.00   0.50    1.60    --  113.25 -95.00 150.00   98
 26  ω     56.00  82.00   0.50    1.60    --  113.25-125.00   0.00   52
 27  ω     97.00 175.00   0.50    1.60    --  113.25  61.00-150.00  156
 28  ω     99.00 178.00   0.50    1.60    --  113.25  30.00 150.00  158
 29  ω    101.00 126.00   0.50    1.60    --  113.25  45.00 150.00   50
 30  ω     42.00 106.00   0.50    1.60    --  113.25 -95.00 -30.00  128
 31  ω     73.00  99.00   0.50    1.60    --  113.25-125.00  30.00   52
 32  ω     41.00  66.00   0.50    1.60    --  113.25 -61.00-150.00   50
 33  ω     41.00  69.00   0.50    1.60    --  113.25 -61.00 -90.00   56
 34  ω     73.00 105.00   0.50    1.60    --  113.25 -95.00  30.00   64
 35  ω     95.00 133.00   0.50    1.60    --  113.25  68.00 101.61   76
 36  ω    141.00 178.00   0.50    1.60    --  113.25  68.00 101.61   74
 37  ω     43.00  69.00   0.50    1.60    --  113.25 -79.00 159.96   52
 38  ω     93.00 119.00   0.50    1.60    --  113.25 -79.00 159.96   52
 39  ω     81.00 106.00   0.50    1.60    --  113.25 -95.00 -60.00   50
 40  ω    152.00 178.00   0.50    1.60    --  113.25 125.00-150.00   52
 41  ω     99.00 146.00   0.50    1.60    --  113.25  30.00-150.00   94
 42  ω    114.00 140.00   0.50    1.60    --  113.25  30.00  90.00   52
 43  ω    114.00 144.00   0.50    1.60    --  113.25  15.00  60.00   60
 44  ω     41.00  66.00   0.50    1.60    --  113.25 -61.00  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      -0.0748704000
_diffrn_orient_matrix_UB_12      -0.0069357000
_diffrn_orient_matrix_UB_13      -0.1377015000
_diffrn_orient_matrix_UB_21      0.0009857000
_diffrn_orient_matrix_UB_22      0.0985717000
_diffrn_orient_matrix_UB_23      -0.0108114000
_diffrn_orient_matrix_UB_31      0.1874897000
_diffrn_orient_matrix_UB_32      -0.0034234000
_diffrn_orient_matrix_UB_33      -0.0378912000
_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                2660
_reflns_number_total             2779
_reflns_odcompleteness_completeness 98.64
_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.102a 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (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         0.330
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.031
_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)+(0.0384P)²+0.7717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6A)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.19222(11) 0.46576(6) 0.73243(8) 0.01954(19) Uani 1 1 d . . . . .
O2 O -0.03343(12) 0.53830(6) 0.87558(8) 0.0210(2) Uani 1 1 d . . . . .
O3 O 0.22940(12) 0.22598(6) 1.03066(9) 0.0225(2) Uani 1 1 d . . . . .
O4 O 0.35972(12) 0.34815(6) 1.08282(8) 0.0231(2) Uani 1 1 d . . . . .
O5 O 0.33066(12) 0.52058(6) 0.52764(8) 0.0215(2) Uani 1 1 d . . . . .
O6 O 0.39172(13) 0.57990(6) 0.71123(9) 0.0255(2) Uani 1 1 d . . . . .
O7 O 0.74688(11) 0.27237(6) 0.85358(9) 0.0245(2) Uani 1 1 d . . . . .
O8 O 0.72518(12) 0.38901(6) 0.96174(9) 0.0236(2) Uani 1 1 d . . . . .
N1 N 0.09782(12) 0.43924(6) 0.76685(9) 0.0138(2) Uani 1 1 d . . . . .
N2 N 0.17912(13) 0.33870(7) 0.90827(9) 0.0149(2) Uani 1 1 d . . . . .
N3 N 0.41302(13) 0.43959(6) 0.69205(9) 0.0151(2) Uani 1 1 d . . . . .
N4 N 0.49260(12) 0.34280(7) 0.83749(9) 0.0156(2) Uani 1 1 d . . . . .
N5 N 0.16903(13) 0.35360(6) 0.59546(9) 0.0146(2) Uani 1 1 d . . . . .
N6 N 0.27802(13) 0.23952(7) 0.75015(10) 0.0154(2) Uani 1 1 d . . . . .
H6 H 0.307(2) 0.1914(12) 0.7878(16) 0.023(4) Uiso 1 1 d . . . . .
N7 N -0.05588(13) 0.48350(7) 0.79552(9) 0.0155(2) Uani 1 1 d . . . . .
N8 N 0.26300(13) 0.30235(7) 1.01344(9) 0.0175(2) Uani 1 1 d . . . . .
N9 N 0.37386(13) 0.51873(7) 0.63995(10) 0.0175(2) Uani 1 1 d . . . . .
N10 N 0.66817(13) 0.33532(7) 0.88560(10) 0.0183(2) Uani 1 1 d . . . . .
N11 N 0.01366(14) 0.39313(7) 0.38934(10) 0.0217(2) Uani 1 1 d . . . . .
C1 C 0.22930(15) 0.42511(8) 0.87295(11) 0.0146(2) Uani 1 1 d . . . . .
H1 H 0.217927 0.467539 0.940919 0.018 Uiso 1 1 calc R U . . .
C2 C 0.41820(15) 0.42820(8) 0.82658(11) 0.0153(2) Uani 1 1 d . . . . .
H2 H 0.495613 0.471516 0.873494 0.018 Uiso 1 1 calc R U . . .
C3 C 0.06702(15) 0.35624(7) 0.70068(11) 0.0140(2) Uani 1 1 d . . . . .
H3 H -0.060490 0.348179 0.672699 0.017 Uiso 1 1 calc R U . . .
C4 C 0.13554(15) 0.28426(8) 0.79437(11) 0.0147(2) Uani 1 1 d . . . . .
H4 H 0.038737 0.243430 0.807330 0.018 Uiso 1 1 calc R U . . .
C5 C 0.35856(15) 0.36107(8) 0.62532(11) 0.0151(2) Uani 1 1 d . . . . .
H5 H 0.419911 0.354596 0.548998 0.018 Uiso 1 1 calc R U . . .
C6 C 0.42227(15) 0.29117(8) 0.72519(11) 0.0151(2) Uani 1 1 d . . . . .
H6A H 0.516927 0.255021 0.695540 0.018 Uiso 1 1 calc R U . . .
C7 C 0.08968(15) 0.37734(7) 0.48421(11) 0.0157(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
O1 N7 1.2165(13) . ?
O2 N7 1.2152(14) . ?
O3 N8 1.2366(15) . ?
O4 N8 1.2251(14) . ?
O5 N9 1.2241(14) . ?
O6 N9 1.2244(14) . ?
O7 N10 1.2224(15) . ?
O8 N10 1.2209(15) . ?
N1 N7 1.4301(13) . ?
N1 C1 1.4590(14) . ?
N1 C3 1.4848(15) . ?
N2 N8 1.3669(14) . ?
N2 C1 1.4633(15) . ?
N2 C4 1.5031(15) . ?
N3 N9 1.3756(14) . ?
N3 C2 1.4626(15) . ?
N3 C5 1.4584(15) . ?
N4 N10 1.3950(14) . ?
N4 C2 1.4480(15) . ?
N4 C6 1.5068(15) . ?
N5 C3 1.4520(15) . ?
N5 C5 1.4597(15) . ?
N5 C7 1.3397(15) . ?
N6 H6 0.870(18) . ?
N6 C4 1.4239(15) . ?
N6 C6 1.4190(15) . ?
N11 C7 1.1499(17) . ?
C1 H1 1.0000 . ?
C1 C2 1.5868(16) . ?
C2 H2 1.0000 . ?
C3 H3 1.0000 . ?
C3 C4 1.5637(16) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C5 C6 1.5739(16) . ?
C6 H6A 1.0000 . ?

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
N7 N1 C1 114.68(9) . . ?
N7 N1 C3 115.70(9) . . ?
C1 N1 C3 107.90(9) . . ?
N8 N2 C1 119.04(9) . . ?
N8 N2 C4 119.36(10) . . ?
C1 N2 C4 110.28(9) . . ?
N9 N3 C2 119.83(10) . . ?
N9 N3 C5 120.79(10) . . ?
C5 N3 C2 111.44(9) . . ?
N10 N4 C2 117.60(10) . . ?
N10 N4 C6 120.10(9) . . ?
C2 N4 C6 108.80(9) . . ?
C3 N5 C5 115.79(9) . . ?
C7 N5 C3 117.75(10) . . ?
C7 N5 C5 121.32(10) . . ?
C4 N6 H6 115.4(11) . . ?
C6 N6 H6 114.6(11) . . ?
C6 N6 C4 115.51(10) . . ?
O1 N7 N1 116.61(10) . . ?
O2 N7 O1 127.24(10) . . ?
O2 N7 N1 116.00(9) . . ?
O3 N8 N2 115.94(10) . . ?
O4 N8 O3 126.23(10) . . ?
O4 N8 N2 117.80(11) . . ?
O5 N9 O6 127.32(11) . . ?
O5 N9 N3 116.80(10) . . ?
O6 N9 N3 115.84(10) . . ?
O7 N10 N4 116.67(10) . . ?
O8 N10 O7 126.15(10) . . ?
O8 N10 N4 116.99(10) . . ?
N1 C1 N2 99.51(9) . . ?
N1 C1 H1 111.7 . . ?
N1 C1 C2 108.87(9) . . ?
N2 C1 H1 111.7 . . ?
N2 C1 C2 112.75(9) . . ?
C2 C1 H1 111.7 . . ?
N3 C2 C1 113.16(9) . . ?
N3 C2 H2 111.9 . . ?
N4 C2 N3 99.20(9) . . ?
N4 C2 C1 108.20(9) . . ?
N4 C2 H2 111.9 . . ?
C1 C2 H2 111.9 . . ?
N1 C3 H3 110.7 . . ?
N1 C3 C4 106.76(9) . . ?
N5 C3 N1 109.38(9) . . ?
N5 C3 H3 110.7 . . ?
N5 C3 C4 108.43(9) . . ?
C4 C3 H3 110.7 . . ?
N2 C4 C3 98.91(9) . . ?
N2 C4 H4 110.2 . . ?
N6 C4 N2 116.26(9) . . ?
N6 C4 C3 110.45(9) . . ?
N6 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
N3 C5 N5 113.62(9) . . ?
N3 C5 H5 111.0 . . ?
N3 C5 C6 101.00(9) . . ?
N5 C5 H5 111.0 . . ?
N5 C5 C6 108.85(9) . . ?
C6 C5 H5 111.0 . . ?
N4 C6 C5 103.91(9) . . ?
N4 C6 H6A 110.6 . . ?
N6 C6 N4 111.53(9) . . ?
N6 C6 C5 109.50(9) . . ?
N6 C6 H6A 110.6 . . ?
C5 C6 H6A 110.6 . . ?
N11 C7 N5 175.29(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6 O6 0.870(18) 2.312(18) 2.8605(14) 121.1(13) 2_546 yes
N6 H6 N11 0.870(18) 2.254(18) 3.0351(15) 149.4(15) 4_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N3 -2.94(13) . . . . ?
N1 C1 C2 N4 -111.82(10) . . . . ?
N1 C3 C4 N2 5.91(11) . . . . ?
N1 C3 C4 N6 -116.54(10) . . . . ?
N2 C1 C2 N3 106.49(11) . . . . ?
N2 C1 C2 N4 -2.39(13) . . . . ?
N3 C5 C6 N4 3.83(11) . . . . ?
N3 C5 C6 N6 123.09(10) . . . . ?
N5 C3 C4 N2 123.66(9) . . . . ?
N5 C3 C4 N6 1.22(13) . . . . ?
N5 C5 C6 N4 -116.01(10) . . . . ?
N5 C5 C6 N6 3.25(13) . . . . ?
N7 N1 C1 N2 94.54(10) . . . . ?
N7 N1 C1 C2 -147.32(9) . . . . ?
N7 N1 C3 N5 132.05(10) . . . . ?
N7 N1 C3 C4 -110.83(10) . . . . ?
N8 N2 C1 N1 -174.72(9) . . . . ?
N8 N2 C1 C2 70.08(13) . . . . ?
N8 N2 C4 N6 -54.96(14) . . . . ?
N8 N2 C4 C3 -173.10(9) . . . . ?
N9 N3 C2 N4 -170.46(9) . . . . ?
N9 N3 C2 C1 75.12(13) . . . . ?
N9 N3 C5 N5 -60.17(13) . . . . ?
N9 N3 C5 C6 -176.54(9) . . . . ?
N10 N4 C2 N3 104.99(11) . . . . ?
N10 N4 C2 C1 -136.81(10) . . . . ?
N10 N4 C6 N6 123.11(11) . . . . ?
N10 N4 C6 C5 -119.03(11) . . . . ?
C1 N1 N7 O1 -149.16(10) . . . . ?
C1 N1 N7 O2 34.99(14) . . . . ?
C1 N1 C3 N5 -97.97(10) . . . . ?
C1 N1 C3 C4 19.15(11) . . . . ?
C1 N2 N8 O3 -171.97(10) . . . . ?
C1 N2 N8 O4 9.85(15) . . . . ?
C1 N2 C4 N6 88.34(12) . . . . ?
C1 N2 C4 C3 -29.81(11) . . . . ?
C2 N3 N9 O5 -163.17(10) . . . . ?
C2 N3 N9 O6 19.05(15) . . . . ?
C2 N3 C5 N5 88.71(12) . . . . ?
C2 N3 C5 C6 -27.66(11) . . . . ?
C2 N4 N10 O7 -153.64(11) . . . . ?
C2 N4 N10 O8 31.04(15) . . . . ?
C2 N4 C6 N6 -97.16(11) . . . . ?
C2 N4 C6 C5 20.70(11) . . . . ?
C3 N1 N7 O1 -22.54(14) . . . . ?
C3 N1 N7 O2 161.62(10) . . . . ?
C3 N1 C1 N2 -36.00(11) . . . . ?
C3 N1 C1 C2 82.14(11) . . . . ?
C3 N5 C5 N3 -58.07(13) . . . . ?
C3 N5 C5 C6 53.60(13) . . . . ?
C4 N2 N8 O3 -31.87(14) . . . . ?
C4 N2 N8 O4 149.96(10) . . . . ?
C4 N2 C1 N1 41.86(11) . . . . ?
C4 N2 C1 C2 -73.35(11) . . . . ?
C4 N6 C6 N4 55.90(13) . . . . ?
C4 N6 C6 C5 -58.54(13) . . . . ?
C5 N3 N9 O5 -16.85(15) . . . . ?
C5 N3 N9 O6 165.37(10) . . . . ?
C5 N3 C2 N4 40.32(11) . . . . ?
C5 N3 C2 C1 -74.09(12) . . . . ?
C5 N5 C3 N1 60.19(12) . . . . ?
C5 N5 C3 C4 -55.87(12) . . . . ?
C6 N4 N10 O7 -17.31(15) . . . . ?
C6 N4 N10 O8 167.37(10) . . . . ?
C6 N4 C2 N3 -35.89(11) . . . . ?
C6 N4 C2 C1 82.32(11) . . . . ?
C6 N6 C4 N2 -55.17(14) . . . . ?
C6 N6 C4 C3 56.45(13) . . . . ?
C7 N5 C3 N1 -94.84(12) . . . . ?
C7 N5 C3 C4 149.10(10) . . . . ?
C7 N5 C5 N3 96.00(13) . . . . ?
C7 N5 C5 C6 -152.34(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 1.163
_oxdiff_exptl_absorpt_empirical_full_min 0.865
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_23-VVP2304
_database_code_depnum_ccdc_archive 'CCDC 2308199'
loop_
_audit_author_name
_audit_author_address
'Aida I Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_23-VVP2304          
;
PROBLEM: Short Inter D...A Contact  O1       ..N9       .       2.84 Ang.  
RESPONSE: : Short distance between two atoms arises due to the peculiarity
of the molecular structure.
;
_vrf_PLAT230_23-VVP2304          
;
PROBLEM: Hirshfeld Test Diff for    O7       --N10      .        5.6 s.u.  
RESPONSE: ...
;
# end Validation Reply Form
_audit_creation_date             2023-06-19
_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 H6 N12 O8'
_chemical_formula_sum            'C8 H6 N12 O8'
_chemical_formula_weight         398.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H6 N12 O8'
_chemical_oxdiff_usercomment     VVP2304
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                   7.78897(7)
_cell_length_b                   13.33467(14)
_cell_length_c                   13.43040(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.7723(8)
_cell_angle_gamma                90
_cell_volume                     1391.90(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15518
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      77.4980
_cell_measurement_theta_min      4.6570
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (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            colorless
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0253
0 -1 0 0.0175
0 0 -1 0.0288
0 0 1 0.0172
-1 0 0 0.1163
1 0 0 0.1182

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 0.9992 -0.0011 -0.0421 -0.1060 -0.0173
-0.0000 -0.9992 0.0011 0.0421 0.1060 0.0173
0.0002 -0.0008 -0.9991 0.1069 -0.0419 -0.0034
-0.0002 0.0008 0.9991 -0.1069 0.0419 0.0034
-0.9994 -0.0004 -0.0008 0.0069 -0.0344 0.1950
0.9994 0.0004 0.0008 -0.0069 0.0344 -0.1950

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18672
_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         77.708
_diffrn_reflns_theta_min         4.678
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(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 -48.00   0.50    0.50    --  -48.70-163.00  55.00  144
  2  ω    -83.00  -7.00   0.50    0.50    --  -48.70 117.00 -67.00  152
  3  ω   -139.00 -48.00   0.50    1.80    --  -86.25-163.00  55.00  182
  4  ω   -154.00 -78.00   0.50    1.80    --  -86.25-117.00-155.00  152
  5  ω     40.00 109.00   0.50    1.80    --  107.75-117.00-155.00  138
  6  ω     54.00 138.00   0.50    1.80    --  107.75-163.00  55.00  168
  7  ω    100.00 176.00   0.50    1.80    --  107.75 117.00 -67.00  152
  8  ω    -26.00  26.00   0.50    0.50    --  -48.70  19.00-120.00  104
  9  ω   -118.00 -73.00   0.50    0.50    --  -48.70-125.00 -90.00   90
 10  ω    -26.00  26.00   0.50    0.50    --  -48.70  19.00 120.00  104
 11  ω     54.00 108.00   0.50    0.50    --   48.70-163.00  55.00  108
 12  ω     34.00  59.00   0.50    0.50    --   48.70-117.00-155.00   50
 13  ω    -24.00  23.00   0.50    0.50    --   48.70 -19.00 -60.00   94
 14  ω    -50.00 -14.00   0.50    1.80    --  -86.25  45.00 150.00   72
 15  ω    147.00 173.00   0.50    1.80    --  107.75  15.00 120.00   52
 16  ω     38.00  92.00   0.50    1.80    --  107.75-103.00-129.42  108
 17  ω     36.00  71.00   0.50    1.80    --  107.75 -61.00   0.00   70
 18  ω     63.00  88.00   0.50    1.80    --  107.75 -77.00   0.00   50
 19  ω     51.00 110.00   0.50    1.80    --  107.75-125.00-120.00  118
 20  ω     45.00  78.00   0.50    1.80    --  107.75 -95.00  60.00   66
 21  ω     96.00 129.00   0.50    1.80    --  107.75 125.00 120.00   66
 22  ω     98.00 160.00   0.50    1.80    --  107.75  45.00  90.00  124
 23  ω     36.00  61.00   0.50    1.80    --  107.75 -61.00 -90.00   50
 24  ω     42.00  69.00   0.50    1.80    --  107.75 -61.00  30.00   54
 25  ω     67.00 105.00   0.50    1.80    --  107.75-125.00 -30.00   76
 26  ω    121.00 176.00   0.50    1.80    --  107.75 125.00 -90.00  110
 27  ω     87.00 163.00   0.50    1.80    --  107.75  77.00 -30.00  152
 28  ω     39.00  74.00   0.50    1.80    --  107.75-106.00-118.49   70
 29  ω     82.00 107.00   0.50    1.80    --  107.75-106.00-118.49   50
 30  ω    114.00 171.00   0.50    1.80    --  107.75  45.00-120.00  114
 31  ω     37.00  76.00   0.50    1.80    --  107.75 -77.00 -60.00   78
 32  ω    128.00 154.00   0.50    1.80    --  107.75  45.00 -90.00   52
 33  ω    105.00 131.00   0.50    1.80    --  107.75  30.00 150.00   52
 34  ω     76.00 102.00   0.50    1.80    --  107.75 -77.00-150.00   52
 35  ω     41.00  67.00   0.50    1.80    --  107.75 -77.00 150.00   52
 36  ω     64.00  90.00   0.50    1.80    --  107.75 -95.00   0.00   52
 37  ω     66.00 103.00   0.50    1.80    --  107.75-125.00  90.00   74
 38  ω    130.00 156.00   0.50    1.80    --  107.75  15.00  90.00   52
 39  ω    137.00 163.00   0.50    1.80    --  107.75  15.00 -90.00   52
 40  ω     97.00 130.00   0.50    1.80    --  107.75  15.00 -90.00   66
 41  ω    114.00 140.00   0.50    1.80    --  107.75  45.00 -60.00   52
 42  ω    130.00 155.00   0.50    1.80    --  107.75 125.00 120.00   50
 43  ω     82.00 108.00   0.50    1.80    --  107.75 -79.00  84.18   52
 44  ω     36.00  94.00   0.50    1.80    --  107.75 -77.00-120.00  116
;
_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      -0.0067641000
_diffrn_orient_matrix_UB_12      -0.0422181000
_diffrn_orient_matrix_UB_13      -0.1069891000
_diffrn_orient_matrix_UB_21      0.0344227000
_diffrn_orient_matrix_UB_22      -0.1060866000
_diffrn_orient_matrix_UB_23      0.0420729000
_diffrn_orient_matrix_UB_31      -0.1950591000
_diffrn_orient_matrix_UB_32      -0.0173562000
_diffrn_orient_matrix_UB_33      0.0034142000
_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                2852
_reflns_number_total             2957
_reflns_odcompleteness_completeness 98.88
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (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         0.302
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.042
_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)+(0.0405P)²+0.7810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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 0.48891(11) 0.69048(6) 0.19450(6) 0.01633(18) Uani 1 1 d . . . . .
O2 O 0.50910(11) 0.59270(7) 0.06489(6) 0.01896(19) Uani 1 1 d . . . . .
O3 O 1.20966(11) 0.55698(7) 0.22911(7) 0.01943(19) Uani 1 1 d . . . . .
O4 O 1.08639(13) 0.55187(9) 0.07934(7) 0.0320(3) Uani 1 1 d . . . . .
O5 O 0.27351(10) 0.35271(7) 0.24896(7) 0.01765(19) Uani 1 1 d . . . . .
O6 O 0.37874(12) 0.31213(7) 0.10849(6) 0.0215(2) Uani 1 1 d . . . . .
O7 O 0.98789(11) 0.23290(6) 0.28354(7) 0.01915(19) Uani 1 1 d . . . . .
O8 O 0.93817(12) 0.26704(7) 0.12485(7) 0.0229(2) Uani 1 1 d . . . . .
N1 N 0.70571(12) 0.58417(7) 0.19098(7) 0.0115(2) Uani 1 1 d . . . . .
N2 N 0.94483(12) 0.49232(7) 0.20777(7) 0.0127(2) Uani 1 1 d . . . . .
N3 N 0.52710(12) 0.41861(7) 0.21282(7) 0.0116(2) Uani 1 1 d . . . . .
N4 N 0.76820(12) 0.32912(7) 0.23518(7) 0.0125(2) Uani 1 1 d . . . . .
N5 N 0.60388(12) 0.52922(7) 0.34947(7) 0.0120(2) Uani 1 1 d . . . . .
N6 N 0.88761(12) 0.43461(7) 0.37141(7) 0.0127(2) Uani 1 1 d . . . . .
N7 N 0.55673(12) 0.62446(7) 0.14741(7) 0.0127(2) Uani 1 1 d . . . . .
N8 N 1.09042(13) 0.53927(8) 0.16885(8) 0.0167(2) Uani 1 1 d . . . . .
N9 N 0.38304(12) 0.35451(7) 0.18846(7) 0.0138(2) Uani 1 1 d . . . . .
N10 N 0.90829(12) 0.27365(7) 0.21273(8) 0.0155(2) Uani 1 1 d . . . . .
N11 N 0.39128(14) 0.61686(8) 0.44926(8) 0.0198(2) Uani 1 1 d . . . . .
N12 N 1.13982(14) 0.37830(8) 0.48121(8) 0.0202(2) Uani 1 1 d . . . . .
C1 C 0.78397(14) 0.49680(8) 0.14621(8) 0.0124(2) Uani 1 1 d . . . . .
H1 H 0.804339 0.508528 0.074392 0.015 Uiso 1 1 calc R U . . .
C2 C 0.68155(14) 0.39550(8) 0.16130(8) 0.0126(2) Uani 1 1 d . . . . .
H2 H 0.653427 0.360302 0.096525 0.015 Uiso 1 1 calc R U . . .
C3 C 0.73609(14) 0.58303(8) 0.30005(8) 0.0112(2) Uani 1 1 d . . . . .
H3 H 0.751246 0.652518 0.327212 0.013 Uiso 1 1 calc R U . . .
C4 C 0.90923(14) 0.52274(8) 0.31068(8) 0.0118(2) Uani 1 1 d . . . . .
H4 H 1.004298 0.565833 0.340511 0.014 Uiso 1 1 calc R U . . .
C5 C 0.57707(14) 0.42534(8) 0.32153(8) 0.0115(2) Uani 1 1 d . . . . .
H5 H 0.486994 0.394247 0.361375 0.014 Uiso 1 1 calc R U . . .
C6 C 0.75135(14) 0.36608(8) 0.33670(8) 0.0122(2) Uani 1 1 d . . . . .
H6 H 0.740994 0.309232 0.384497 0.015 Uiso 1 1 calc R U . . .
C7 C 0.48921(15) 0.57733(9) 0.40212(8) 0.0132(2) Uani 1 1 d . . . . .
C8 C 1.02344(15) 0.40165(9) 0.42917(8) 0.0141(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
O1 N7 1.2239(13) . ?
O2 N7 1.2211(13) . ?
O3 N8 1.2143(14) . ?
O4 N8 1.2123(15) . ?
O5 N9 1.2165(13) . ?
O6 N9 1.2122(14) . ?
O7 N10 1.2274(14) . ?
O8 N10 1.2211(14) . ?
N1 N7 1.3742(13) . ?
N1 C1 1.4625(14) . ?
N1 C3 1.4685(14) . ?
N2 N8 1.4245(13) . ?
N2 C1 1.4563(14) . ?
N2 C4 1.4839(14) . ?
N3 N9 1.4311(13) . ?
N3 C2 1.4597(14) . ?
N3 C5 1.4887(14) . ?
N4 N10 1.3682(13) . ?
N4 C2 1.4613(14) . ?
N4 C6 1.4638(14) . ?
N5 C3 1.4511(14) . ?
N5 C5 1.4468(14) . ?
N5 C7 1.3388(15) . ?
N6 C4 1.4466(14) . ?
N6 C6 1.4539(14) . ?
N6 C8 1.3440(15) . ?
N11 C7 1.1506(16) . ?
N12 C8 1.1506(16) . ?
C1 H1 1.0000 . ?
C1 C2 1.5885(15) . ?
C2 H2 1.0000 . ?
C3 H3 1.0000 . ?
C3 C4 1.5684(15) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C5 C6 1.5723(15) . ?
C6 H6 1.0000 . ?

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
N7 N1 C1 119.97(9) . . ?
N7 N1 C3 120.33(9) . . ?
C1 N1 C3 110.96(9) . . ?
N8 N2 C1 116.71(9) . . ?
N8 N2 C4 115.06(9) . . ?
C1 N2 C4 108.13(8) . . ?
N9 N3 C2 115.07(9) . . ?
N9 N3 C5 114.25(9) . . ?
C2 N3 C5 107.89(8) . . ?
N10 N4 C2 121.15(9) . . ?
N10 N4 C6 120.59(9) . . ?
C2 N4 C6 111.27(9) . . ?
C5 N5 C3 116.70(9) . . ?
C7 N5 C3 121.52(10) . . ?
C7 N5 C5 120.39(10) . . ?
C4 N6 C6 116.07(9) . . ?
C8 N6 C4 118.34(9) . . ?
C8 N6 C6 120.65(9) . . ?
O1 N7 N1 116.25(9) . . ?
O2 N7 O1 127.07(10) . . ?
O2 N7 N1 116.65(9) . . ?
O3 N8 N2 115.68(10) . . ?
O4 N8 O3 127.07(10) . . ?
O4 N8 N2 117.10(10) . . ?
O5 N9 N3 115.65(9) . . ?
O6 N9 O5 127.07(10) . . ?
O6 N9 N3 117.17(9) . . ?
O7 N10 N4 115.98(10) . . ?
O8 N10 O7 126.75(10) . . ?
O8 N10 N4 117.23(10) . . ?
N1 C1 H1 111.6 . . ?
N1 C1 C2 113.49(9) . . ?
N2 C1 N1 99.53(8) . . ?
N2 C1 H1 111.6 . . ?
N2 C1 C2 108.25(9) . . ?
C2 C1 H1 111.6 . . ?
N3 C2 N4 99.45(9) . . ?
N3 C2 C1 108.51(9) . . ?
N3 C2 H2 111.8 . . ?
N4 C2 C1 112.85(9) . . ?
N4 C2 H2 111.8 . . ?
C1 C2 H2 111.8 . . ?
N1 C3 H3 111.2 . . ?
N1 C3 C4 100.21(8) . . ?
N5 C3 N1 112.88(9) . . ?
N5 C3 H3 111.2 . . ?
N5 C3 C4 109.68(9) . . ?
C4 C3 H3 111.2 . . ?
N2 C4 C3 105.52(8) . . ?
N2 C4 H4 110.6 . . ?
N6 C4 N2 109.81(9) . . ?
N6 C4 C3 109.65(9) . . ?
N6 C4 H4 110.6 . . ?
C3 C4 H4 110.6 . . ?
N3 C5 H5 110.6 . . ?
N3 C5 C6 105.35(8) . . ?
N5 C5 N3 109.64(9) . . ?
N5 C5 H5 110.6 . . ?
N5 C5 C6 109.81(9) . . ?
C6 C5 H5 110.6 . . ?
N4 C6 C5 100.25(8) . . ?
N4 C6 H6 111.0 . . ?
N6 C6 N4 113.70(9) . . ?
N6 C6 C5 109.36(9) . . ?
N6 C6 H6 111.0 . . ?
C5 C6 H6 111.0 . . ?
N11 C7 N5 178.24(13) . . ?
N12 C8 N6 176.33(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
N1 C1 C2 N3 3.07(12) . . . . ?
N1 C1 C2 N4 -106.14(10) . . . . ?
N1 C3 C4 N2 -4.01(10) . . . . ?
N1 C3 C4 N6 -122.22(9) . . . . ?
N2 C1 C2 N3 112.54(10) . . . . ?
N2 C1 C2 N4 3.33(12) . . . . ?
N3 C5 C6 N4 -3.49(10) . . . . ?
N3 C5 C6 N6 116.28(9) . . . . ?
N5 C3 C4 N2 114.93(9) . . . . ?
N5 C3 C4 N6 -3.28(12) . . . . ?
N5 C5 C6 N4 -121.48(9) . . . . ?
N5 C5 C6 N6 -1.71(12) . . . . ?
N7 N1 C1 N2 171.99(9) . . . . ?
N7 N1 C1 C2 -73.22(12) . . . . ?
N7 N1 C3 N5 58.71(13) . . . . ?
N7 N1 C3 C4 175.29(9) . . . . ?
N8 N2 C1 N1 -95.85(10) . . . . ?
N8 N2 C1 C2 145.41(9) . . . . ?
N8 N2 C4 N6 -129.79(10) . . . . ?
N8 N2 C4 C3 112.11(10) . . . . ?
N9 N3 C2 N4 -92.82(10) . . . . ?
N9 N3 C2 C1 149.09(9) . . . . ?
N9 N3 C5 N5 -133.46(9) . . . . ?
N9 N3 C5 C6 108.43(10) . . . . ?
N10 N4 C2 N3 168.68(9) . . . . ?
N10 N4 C2 C1 -76.52(12) . . . . ?
N10 N4 C6 N6 62.00(13) . . . . ?
N10 N4 C6 C5 178.57(9) . . . . ?
C1 N1 N7 O1 172.49(9) . . . . ?
C1 N1 N7 O2 -9.55(14) . . . . ?
C1 N1 C3 N5 -88.84(11) . . . . ?
C1 N1 C3 C4 27.73(11) . . . . ?
C1 N2 N8 O3 162.41(10) . . . . ?
C1 N2 N8 O4 -21.72(15) . . . . ?
C1 N2 C4 N6 97.73(10) . . . . ?
C1 N2 C4 C3 -20.37(11) . . . . ?
C2 N3 N9 O5 159.57(10) . . . . ?
C2 N3 N9 O6 -23.97(14) . . . . ?
C2 N3 C5 N5 97.21(10) . . . . ?
C2 N3 C5 C6 -20.90(11) . . . . ?
C2 N4 N10 O7 168.86(10) . . . . ?
C2 N4 N10 O8 -13.40(15) . . . . ?
C2 N4 C6 N6 -89.05(11) . . . . ?
C2 N4 C6 C5 27.52(11) . . . . ?
C3 N1 N7 O1 27.82(14) . . . . ?
C3 N1 N7 O2 -154.22(10) . . . . ?
C3 N1 C1 N2 -40.32(11) . . . . ?
C3 N1 C1 C2 74.47(11) . . . . ?
C3 N5 C5 N3 -59.89(12) . . . . ?
C3 N5 C5 C6 55.41(12) . . . . ?
C4 N2 N8 O3 34.11(14) . . . . ?
C4 N2 N8 O4 -150.03(11) . . . . ?
C4 N2 C1 N1 35.74(10) . . . . ?
C4 N2 C1 C2 -83.00(10) . . . . ?
C4 N6 C6 N4 56.89(13) . . . . ?
C4 N6 C6 C5 -54.23(12) . . . . ?
C5 N3 N9 O5 33.93(13) . . . . ?
C5 N3 N9 O6 -149.61(10) . . . . ?
C5 N3 C2 N4 36.04(10) . . . . ?
C5 N3 C2 C1 -82.05(10) . . . . ?
C5 N5 C3 N1 58.13(12) . . . . ?
C5 N5 C3 C4 -52.68(12) . . . . ?
C6 N4 N10 O7 20.67(14) . . . . ?
C6 N4 N10 O8 -161.59(10) . . . . ?
C6 N4 C2 N3 -40.46(11) . . . . ?
C6 N4 C2 C1 74.34(11) . . . . ?
C6 N6 C4 N2 -58.45(12) . . . . ?
C6 N6 C4 C3 57.06(12) . . . . ?
C7 N5 C3 N1 -108.50(11) . . . . ?
C7 N5 C3 C4 140.69(10) . . . . ?
C7 N5 C5 N3 106.91(11) . . . . ?
C7 N5 C5 C6 -137.80(10) . . . . ?
C8 N6 C4 N2 96.87(11) . . . . ?
C8 N6 C4 C3 -147.62(10) . . . . ?
C8 N6 C6 N4 -97.82(12) . . . . ?
C8 N6 C6 C5 151.06(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 1.102
_oxdiff_exptl_absorpt_empirical_full_min 0.883
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_15-PGV2061
_database_code_depnum_ccdc_archive 'CCDC 2308197'
loop_
_audit_author_name
_audit_author_address
'Aida I Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT430_15-PGV2061          
;
PROBLEM: Short Inter D...A Contact  O9       ..N10      .       2.89 Ang.  
RESPONSE: These intermolecular interactions are expected for this structure.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 N14 O14'
_chemical_formula_sum            'C9 H8 N14 O14'
_chemical_formula_weight         536.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H8N14O14
_chemical_oxdiff_usercomment     PGV2061
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                   13.5629(4)
_cell_length_b                   8.4701(3)
_cell_length_c                   17.2484(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.891(3)
_cell_angle_gamma                90
_cell_volume                     1863.27(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14217
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.6700
_cell_measurement_theta_min      3.4870
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (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            colorless
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0081
0 0 1 0.0148
-1 -1 1 0.0325
1 1 -1 0.0306
-1 1 1 0.0379
1 -1 -1 0.0138

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_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
0.0021 -0.0001 -1.0009 0.0147 -0.0772 -0.0532
-0.0021 0.0001 1.0009 -0.0147 0.0772 0.0532
-1.0010 -0.9990 0.9975 0.1931 0.1072 -0.0063
1.0010 0.9990 -0.9975 -0.1931 -0.1072 0.0063
-0.9995 0.9990 0.9990 -0.0382 -0.0801 0.2024
0.9995 -0.9990 -0.9990 0.0382 0.0801 -0.2024

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23475
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         83.954
_diffrn_reflns_theta_min         3.465
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  26.00   0.50    2.00    --  -46.59  74.00 103.00  190
  2  ω   -119.00 -24.00   0.50    2.00    --  -46.59 -74.00 -25.00  190
  3  ω     24.00 120.00   0.50    2.00    --   46.59  74.00 103.00  192
  4  ω    -25.00  69.00   0.50    2.00    --   46.59 -74.00 -25.00  188
  5  ω   -164.00 -69.00   0.50    8.00    --  -91.75 -74.00 -25.00  190
  6  ω    -96.00 -19.00   0.50    8.00    --  -91.75  74.00 103.00  154
  7  ω     91.00 178.00   0.50    8.00    --  113.25  74.00 103.00  174
  8  ω     41.00  96.00   0.50    8.00    --  113.25 -74.00 -25.00  110
  9  ω    -27.00  29.00   0.50    2.00    --  -46.59  19.00 -90.00  112
 10  ω     34.00  93.00   0.50    2.00    --   46.59-125.00 150.00  118
 11  ω    -51.00 -19.00   0.50    8.00    --  -91.75  45.00 -90.00   64
 12  ω     43.00 111.00   0.50    8.00    --  113.25-125.00 -30.00  136
 13  ω     95.00 178.00   0.50    8.00    --  113.25 125.00  30.00  166
 14  ω     41.00 106.00   0.50    8.00    --  113.25 -95.00 -30.00  130
 15  ω     95.00 178.00   0.50    8.00    --  113.25 125.00-180.00  166
 16  ω    106.00 147.00   0.50    8.00    --  113.25 125.00 150.00   82
 17  ω    153.00 178.00   0.50    8.00    --  113.25 125.00 150.00   50
 18  ω    111.00 169.00   0.50    8.00    --  113.25 107.00  62.01  116
 19  ω     44.00  75.00   0.50    8.00    --  113.25-143.00 -62.34   62
 20  ω     90.00 116.00   0.50    8.00    --  113.25-143.00 -62.34   52
 21  ω     42.00  71.00   0.50    8.00    --  113.25 -61.00  30.00   58
 22  ω     85.00 117.00   0.50    8.00    --  113.25-141.00 165.22   64
 23  ω    111.00 149.00   0.50    8.00    --  113.25  30.00  30.00   76
 24  ω     57.00  83.00   0.50    8.00    --  113.25   0.00-180.00   52
 25  ω     96.00 143.00   0.50    8.00    --  113.25  61.00  90.00   94
 26  ω     57.00 142.00   0.50    8.00    --  113.25 -88.00  28.48  170
 27  ω     61.00  96.00   0.50    8.00    --  113.25-125.00   0.00   70
 28  ω     90.00 115.00   0.50    8.00    --  113.25  77.00-180.00   50
 29  ω    131.00 177.00   0.50    8.00    --  113.25  77.00-180.00   92
 30  ω     48.00  74.00   0.50    8.00    --  113.25 -80.00 -37.61   52
 31  ω     45.00  70.00   0.50    8.00    --  113.25 -61.00 -30.00   50
 32  ω     66.00 117.00   0.50    8.00    --  113.25-139.00-143.94  102
 33  ω     98.00 151.00   0.50    8.00    --  113.25 125.00-120.00  106
 34  ω    130.00 177.00   0.50    8.00    --  113.25  77.00 -30.00   94
 35  ω     48.00  74.00   0.50    8.00    --  113.25 -95.00  30.00   52
 36  ω    100.00 143.00   0.50    8.00    --  113.25  45.00 -90.00   86
 37  ω    130.00 169.00   0.50    8.00    --  113.25  30.00-150.00   78
 38  ω    116.00 142.00   0.50    8.00    --  113.25  36.00  33.17   52
 39  ω     41.00  73.00   0.50    8.00    --  113.25 -95.00 -60.00   64
 40  ω    133.00 159.00   0.50    8.00    --  113.25  30.00  60.00   52
 41  ω    127.00 176.00   0.50    8.00    --  113.25   0.00-180.00   98
 42  ω     55.00 106.00   0.50    8.00    --  113.25 -95.00-150.00  102
;
_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      -0.0923291000
_diffrn_orient_matrix_UB_12      -0.1156865000
_diffrn_orient_matrix_UB_13      -0.0148993000
_diffrn_orient_matrix_UB_21      0.0635963000
_diffrn_orient_matrix_UB_22      -0.0938577000
_diffrn_orient_matrix_UB_23      0.0773086000
_diffrn_orient_matrix_UB_31      -0.0451295000
_diffrn_orient_matrix_UB_32      0.1044198000
_diffrn_orient_matrix_UB_33      0.0530001000
_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                3523
_reflns_number_total             4051
_reflns_odcompleteness_completeness 98.90
_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 42.102a 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (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         0.352
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.077
_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)+(0.0340P)²+2.2312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
;
_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 0.43488(10) 0.62874(18) 0.04191(8) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.46171(11) 0.88289(17) 0.05804(9) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.56246(11) 0.76173(18) 0.33626(8) 0.0237(3) Uani 1 1 d . . . . .
O4 O 0.55031(10) 0.97443(17) 0.26210(9) 0.0237(3) Uani 1 1 d . . . . .
O5 O 0.75687(11) 0.63445(17) -0.01095(8) 0.0238(3) Uani 1 1 d . . . . .
O6 O 0.70643(10) 0.87378(17) 0.00690(8) 0.0227(3) Uani 1 1 d . . . . .
O7 O 1.00181(10) 0.80432(17) 0.33837(8) 0.0251(3) Uani 1 1 d . . . . .
O8 O 0.93793(10) 1.00839(16) 0.26001(8) 0.0202(3) Uani 1 1 d . . . . .
O9 O 0.95295(10) 0.32607(17) 0.32931(8) 0.0221(3) Uani 1 1 d . . . . .
O10 O 0.99849(11) 0.2208(2) 0.45160(9) 0.0326(4) Uani 1 1 d . . . . .
O11 O 0.78000(11) 0.11300(17) 0.34074(9) 0.0273(3) Uani 1 1 d . . . . .
O12 O 0.66384(10) 0.29472(17) 0.33736(8) 0.0228(3) Uani 1 1 d . . . . .
O13 O 0.80650(11) 0.2331(2) 0.51203(9) 0.0318(4) Uani 1 1 d . . . . .
O14 O 0.90498(11) 0.44505(19) 0.53739(8) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.59635(11) 0.71676(18) 0.11376(9) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.65715(11) 0.77895(18) 0.25247(9) 0.0148(3) Uani 1 1 d . . . . .
N3 N 0.78965(11) 0.72758(18) 0.11571(9) 0.0145(3) Uani 1 1 d . . . . .
N4 N 0.83974(11) 0.79166(18) 0.24800(9) 0.0141(3) Uani 1 1 d . . . . .
N5 N 0.70168(11) 0.48700(18) 0.12913(9) 0.0143(3) Uani 1 1 d . . . . .
N6 N 0.77273(10) 0.54729(18) 0.28495(8) 0.0134(3) Uani 1 1 d . . . . .
N7 N 0.48828(12) 0.7457(2) 0.06865(9) 0.0194(3) Uani 1 1 d . . . . .
N8 N 0.58319(11) 0.8415(2) 0.28490(9) 0.0183(3) Uani 1 1 d . . . . .
N9 N 0.74685(12) 0.74480(19) 0.03119(9) 0.0174(3) Uani 1 1 d . . . . .
N10 N 0.93334(11) 0.87295(19) 0.28317(9) 0.0168(3) Uani 1 1 d . . . . .
N11 N 0.70477(14) 0.1954(2) 0.14753(12) 0.0281(4) Uani 1 1 d . . . . .
N12 N 0.94017(12) 0.2960(2) 0.39427(10) 0.0200(3) Uani 1 1 d . . . . .
N13 N 0.75296(12) 0.24372(19) 0.35485(9) 0.0191(3) Uani 1 1 d . . . . .
N14 N 0.85050(12) 0.3428(2) 0.49265(9) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.65269(13) 0.8393(2) 0.17144(10) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.616593 0.943958 0.158671 0.018 Uiso 1 1 calc R U . . .
C2 C 0.76821(13) 0.8464(2) 0.16939(10) 0.0149(3) Uani 1 1 d . . . . .
H2 H 0.786730 0.954984 0.156107 0.018 Uiso 1 1 calc R U . . .
C3 C 0.62210(13) 0.5647(2) 0.15560(10) 0.0139(3) Uani 1 1 d . . . . .
H3 H 0.558000 0.497240 0.142560 0.017 Uiso 1 1 calc R U . . .
C4 C 0.66603(12) 0.6047(2) 0.25027(10) 0.0136(3) Uani 1 1 d . . . . .
H4 H 0.621215 0.554452 0.278955 0.016 Uiso 1 1 calc R U . . .
C5 C 0.80222(13) 0.5715(2) 0.15307(10) 0.0139(3) Uani 1 1 d . . . . .
H5 H 0.856034 0.508815 0.138657 0.017 Uiso 1 1 calc R U . . .
C6 C 0.84247(13) 0.6162(2) 0.24700(10) 0.0139(3) Uani 1 1 d . . . . .
H6 H 0.915689 0.577103 0.274465 0.017 Uiso 1 1 calc R U . . .
C7 C 0.70572(14) 0.3295(2) 0.13960(11) 0.0178(4) Uani 1 1 d . . . . .
C8 C 0.81393(13) 0.5320(2) 0.37433(10) 0.0162(3) Uani 1 1 d . . . . .
H8A H 0.762026 0.574463 0.397667 0.019 Uiso 1 1 calc R U . . .
H8B H 0.878712 0.595657 0.396339 0.019 Uiso 1 1 calc R U . . .
C9 C 0.83849(13) 0.3596(2) 0.40196(10) 0.0173(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 N7 1.222(2) . ?
O2 N7 1.212(2) . ?
O3 N8 1.221(2) . ?
O4 N8 1.225(2) . ?
O5 N9 1.220(2) . ?
O6 N9 1.230(2) . ?
O7 N10 1.227(2) . ?
O8 N10 1.223(2) . ?
O9 N12 1.217(2) . ?
O10 N12 1.216(2) . ?
O11 N13 1.217(2) . ?
O12 N13 1.221(2) . ?
O13 N14 1.211(2) . ?
O14 N14 1.226(2) . ?
N1 N7 1.428(2) . ?
N1 C1 1.461(2) . ?
N1 C3 1.459(2) . ?
N2 N8 1.4078(19) . ?
N2 C1 1.470(2) . ?
N2 C4 1.482(2) . ?
N3 N9 1.381(2) . ?
N3 C2 1.462(2) . ?
N3 C5 1.455(2) . ?
N4 N10 1.389(2) . ?
N4 C2 1.449(2) . ?
N4 C6 1.487(2) . ?
N5 C3 1.464(2) . ?
N5 C5 1.469(2) . ?
N5 C7 1.345(2) . ?
N6 C4 1.449(2) . ?
N6 C6 1.444(2) . ?
N6 C8 1.456(2) . ?
N11 C7 1.145(3) . ?
N12 C9 1.528(2) . ?
N13 C9 1.526(2) . ?
N14 C9 1.523(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.580(2) . ?
C2 H2 1.0000 . ?
C3 H3 1.0000 . ?
C3 C4 1.573(2) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C5 C6 1.570(2) . ?
C6 H6 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.537(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
N7 N1 C1 116.81(14) . . ?
N7 N1 C3 116.73(14) . . ?
C3 N1 C1 107.98(13) . . ?
N8 N2 C1 116.26(14) . . ?
N8 N2 C4 117.38(14) . . ?
C1 N2 C4 107.43(13) . . ?
N9 N3 C2 119.53(14) . . ?
N9 N3 C5 120.48(14) . . ?
C5 N3 C2 111.32(13) . . ?
N10 N4 C2 118.12(14) . . ?
N10 N4 C6 118.54(13) . . ?
C2 N4 C6 108.70(13) . . ?
C3 N5 C5 113.93(14) . . ?
C7 N5 C3 113.89(14) . . ?
C7 N5 C5 116.99(14) . . ?
C4 N6 C8 115.89(13) . . ?
C6 N6 C4 113.18(13) . . ?
C6 N6 C8 116.20(13) . . ?
O1 N7 N1 115.67(15) . . ?
O2 N7 O1 127.81(16) . . ?
O2 N7 N1 116.41(15) . . ?
O3 N8 O4 126.37(15) . . ?
O3 N8 N2 116.83(15) . . ?
O4 N8 N2 116.67(15) . . ?
O5 N9 O6 127.20(15) . . ?
O5 N9 N3 117.13(15) . . ?
O6 N9 N3 115.59(15) . . ?
O7 N10 N4 116.23(15) . . ?
O8 N10 O7 126.06(15) . . ?
O8 N10 N4 117.56(14) . . ?
O9 N12 C9 114.93(14) . . ?
O10 N12 O9 126.97(16) . . ?
O10 N12 C9 118.09(15) . . ?
O11 N13 O12 127.81(16) . . ?
O11 N13 C9 117.75(15) . . ?
O12 N13 C9 114.42(15) . . ?
O13 N14 O14 128.04(16) . . ?
O13 N14 C9 117.66(16) . . ?
O14 N14 C9 114.30(15) . . ?
N1 C1 N2 104.06(14) . . ?
N1 C1 H1 112.1 . . ?
N1 C1 C2 107.74(13) . . ?
N2 C1 H1 112.1 . . ?
N2 C1 C2 108.31(13) . . ?
C2 C1 H1 112.1 . . ?
N3 C2 C1 113.59(14) . . ?
N3 C2 H2 111.6 . . ?
N4 C2 N3 99.09(13) . . ?
N4 C2 C1 108.67(13) . . ?
N4 C2 H2 111.6 . . ?
C1 C2 H2 111.6 . . ?
N1 C3 N5 108.69(13) . . ?
N1 C3 H3 110.5 . . ?
N1 C3 C4 105.41(14) . . ?
N5 C3 H3 110.5 . . ?
N5 C3 C4 111.20(13) . . ?
C4 C3 H3 110.5 . . ?
N2 C4 C3 103.62(13) . . ?
N2 C4 H4 110.0 . . ?
N6 C4 N2 113.70(14) . . ?
N6 C4 C3 109.19(13) . . ?
N6 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
N3 C5 N5 111.13(13) . . ?
N3 C5 H5 111.0 . . ?
N3 C5 C6 100.68(13) . . ?
N5 C5 H5 111.0 . . ?
N5 C5 C6 111.78(13) . . ?
C6 C5 H5 111.0 . . ?
N4 C6 C5 104.57(13) . . ?
N4 C6 H6 110.5 . . ?
N6 C6 N4 112.08(14) . . ?
N6 C6 C5 108.61(13) . . ?
N6 C6 H6 110.5 . . ?
C5 C6 H6 110.5 . . ?
N11 C7 N5 177.2(2) . . ?
N6 C8 H8A 109.2 . . ?
N6 C8 H8B 109.2 . . ?
N6 C8 C9 112.19(14) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
N12 C9 C8 114.50(14) . . ?
N13 C9 N12 105.81(14) . . ?
N13 C9 C8 113.62(14) . . ?
N14 C9 N12 105.79(13) . . ?
N14 C9 N13 106.46(14) . . ?
N14 C9 C8 110.06(15) . . ?

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
O9 N12 C9 N13 80.10(18) . . . . ?
O9 N12 C9 N14 -167.19(16) . . . . ?
O9 N12 C9 C8 -45.8(2) . . . . ?
O10 N12 C9 N13 -99.09(19) . . . . ?
O10 N12 C9 N14 13.6(2) . . . . ?
O10 N12 C9 C8 134.99(17) . . . . ?
O11 N13 C9 N12 18.6(2) . . . . ?
O11 N13 C9 N14 -93.69(18) . . . . ?
O11 N13 C9 C8 145.00(16) . . . . ?
O12 N13 C9 N12 -162.98(14) . . . . ?
O12 N13 C9 N14 84.77(17) . . . . ?
O12 N13 C9 C8 -36.5(2) . . . . ?
O13 N14 C9 N12 -101.60(18) . . . . ?
O13 N14 C9 N13 10.7(2) . . . . ?
O13 N14 C9 C8 134.21(17) . . . . ?
O14 N14 C9 N12 78.35(19) . . . . ?
O14 N14 C9 N13 -169.40(15) . . . . ?
O14 N14 C9 C8 -45.8(2) . . . . ?
N1 C1 C2 N3 -2.94(19) . . . . ?
N1 C1 C2 N4 -112.18(15) . . . . ?
N1 C3 C4 N2 1.85(16) . . . . ?
N1 C3 C4 N6 -119.64(14) . . . . ?
N2 C1 C2 N3 109.05(16) . . . . ?
N2 C1 C2 N4 -0.19(19) . . . . ?
N3 C5 C6 N4 3.58(15) . . . . ?
N3 C5 C6 N6 123.40(14) . . . . ?
N5 C3 C4 N2 119.46(14) . . . . ?
N5 C3 C4 N6 -2.03(19) . . . . ?
N5 C5 C6 N4 -114.48(14) . . . . ?
N5 C5 C6 N6 5.34(19) . . . . ?
N6 C8 C9 N12 77.35(17) . . . . ?
N6 C8 C9 N13 -44.38(19) . . . . ?
N6 C8 C9 N14 -163.65(13) . . . . ?
N7 N1 C1 N2 101.39(16) . . . . ?
N7 N1 C1 C2 -143.78(14) . . . . ?
N7 N1 C3 N5 125.61(15) . . . . ?
N7 N1 C3 C4 -115.10(15) . . . . ?
N8 N2 C1 N1 -100.08(16) . . . . ?
N8 N2 C1 C2 145.49(14) . . . . ?
N8 N2 C4 N6 -130.13(14) . . . . ?
N8 N2 C4 C3 111.47(15) . . . . ?
N9 N3 C2 N4 -171.97(14) . . . . ?
N9 N3 C2 C1 72.97(19) . . . . ?
N9 N3 C5 N5 -56.42(19) . . . . ?
N9 N3 C5 C6 -174.95(13) . . . . ?
N10 N4 C2 N3 102.88(16) . . . . ?
N10 N4 C2 C1 -138.31(15) . . . . ?
N10 N4 C6 N6 124.84(15) . . . . ?
N10 N4 C6 C5 -117.70(15) . . . . ?
C1 N1 N7 O1 -157.63(15) . . . . ?
C1 N1 N7 O2 25.9(2) . . . . ?
C1 N1 C3 N5 -100.41(15) . . . . ?
C1 N1 C3 C4 18.88(16) . . . . ?
C1 N2 N8 O3 157.21(15) . . . . ?
C1 N2 N8 O4 -26.6(2) . . . . ?
C1 N2 C4 N6 96.64(15) . . . . ?
C1 N2 C4 C3 -21.76(16) . . . . ?
C2 N3 N9 O5 -171.87(15) . . . . ?
C2 N3 N9 O6 11.1(2) . . . . ?
C2 N3 C5 N5 91.10(16) . . . . ?
C2 N3 C5 C6 -27.43(16) . . . . ?
C2 N4 N10 O7 -163.51(15) . . . . ?
C2 N4 N10 O8 20.6(2) . . . . ?
C2 N4 C6 N6 -96.53(15) . . . . ?
C2 N4 C6 C5 20.94(16) . . . . ?
C3 N1 N7 O1 -27.7(2) . . . . ?
C3 N1 N7 O2 155.78(16) . . . . ?
C3 N1 C1 N2 -32.56(16) . . . . ?
C3 N1 C1 C2 82.28(16) . . . . ?
C3 N5 C5 N3 -61.69(17) . . . . ?
C3 N5 C5 C6 49.93(18) . . . . ?
C4 N2 N8 O3 28.0(2) . . . . ?
C4 N2 N8 O4 -155.83(15) . . . . ?
C4 N2 C1 N1 33.74(16) . . . . ?
C4 N2 C1 C2 -80.69(16) . . . . ?
C4 N6 C6 N4 53.74(18) . . . . ?
C4 N6 C6 C5 -61.29(18) . . . . ?
C4 N6 C8 C9 115.80(16) . . . . ?
C5 N3 N9 O5 -27.0(2) . . . . ?
C5 N3 N9 O6 156.01(15) . . . . ?
C5 N3 C2 N4 40.16(16) . . . . ?
C5 N3 C2 C1 -74.90(17) . . . . ?
C5 N5 C3 N1 64.13(17) . . . . ?
C5 N5 C3 C4 -51.48(18) . . . . ?
C6 N4 N10 O7 -28.7(2) . . . . ?
C6 N4 N10 O8 155.43(15) . . . . ?
C6 N4 C2 N3 -35.96(15) . . . . ?
C6 N4 C2 C1 82.85(16) . . . . ?
C6 N6 C4 N2 -55.44(18) . . . . ?
C6 N6 C4 C3 59.71(18) . . . . ?
C6 N6 C8 C9 -107.62(17) . . . . ?
C7 N5 C3 N1 -158.16(14) . . . . ?
C7 N5 C3 C4 86.23(18) . . . . ?
C7 N5 C5 N3 161.98(15) . . . . ?
C7 N5 C5 C6 -86.40(18) . . . . ?
C8 N6 C4 N2 82.42(18) . . . . ?
C8 N6 C4 C3 -162.42(14) . . . . ?
C8 N6 C6 N4 -84.00(18) . . . . ?
C8 N6 C6 C5 160.98(14) . . . . ?

_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 1.787
_oxdiff_exptl_absorpt_empirical_full_min 0.788
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_22-PGV-2050
_database_code_depnum_ccdc_archive 'CCDC 2308198'
loop_
_audit_author_name
_audit_author_address
'Aida I Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 
Russia
;
_audit_update_record             
;
2023-11-15 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-10-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT430_22-PGV-2050         
;
PROBLEM: Short Inter D...A Contact  O1A      ..N9A      .       2.81 Ang.  
RESPONSE: These intermolecular interactions are expected for this structure.
;
_vrf_PLAT089_22-PGV-2050         
;
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.
;
_vrf_PLAT094_22-PGV-2050         
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.26 Report
RESPONSE: The crystal structure contains a disordered solvent that
cannot be fully modeled.
;
_vrf_PLAT097_22-PGV-2050         
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.76 eA-3  
RESPONSE: The crystal structure contains a disordered solvent that
cannot be fully modeled.
;
_vrf_PLAT340_22-PGV-2050         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00729 Ang.  
RESPONSE: The crystal was small and of poor quality.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 N12 O10, C2 H3 N'
_chemical_formula_sum            'C9 H9 N13 O10'
_chemical_formula_weight         459.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C5H12N10O12
_chemical_oxdiff_usercomment     PGV2050
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                   13.5373(3)
_cell_length_b                   7.8765(2)
_cell_length_c                   32.0668(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3419.17(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8188
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      78.0520
_cell_measurement_theta_min      2.7790
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (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            colorless
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 1 0.0519
1 1 -1 0.0422
-1 1 0 0.0494
-1 -1 0 0.0433
0 0 -1 0.0288
0 0 1 0.0116

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0002 -0.9998 0.9998 -0.0129 -0.2046 0.1069
0.9992 0.9990 -0.9970 0.0283 0.1956 0.1198
-1.0002 0.9997 0.0002 -0.0346 0.1979 -0.1040
-0.9992 -0.9989 -0.0030 0.0192 -0.1889 -0.1228
-0.0000 0.0001 -1.0000 0.0475 0.0067 -0.0029
0.0000 -0.0001 1.0000 -0.0475 -0.0067 0.0029

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            41607
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.984
_diffrn_reflns_theta_min         2.756
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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   -115.00 -60.00   0.50    1.50    --  -40.74-144.00 161.00  110
  2  ω   -115.00 -62.00   0.50    1.50    --  -40.74-142.00  69.00  106
  3  ω    -31.00  42.00   0.50    1.50    --  -40.74   6.00-121.00  146
  4  ω     37.00 100.00   0.50    1.50    --   40.74-129.00-118.00  126
  5  ω    -43.00  31.00   0.50    1.50    --   40.74  -6.00  61.00  148
  6  ω    -89.00 -23.00   0.50    6.20    --  -98.00 129.00 -45.00  132
  7  ω   -177.00 -16.00   0.50    6.20    --  -98.00  -6.00  61.00  322
  8  ω    -88.00 -23.00   0.50    6.20    --  -98.00 127.00  45.00  130
  9  ω     45.00 113.00   0.50    6.20    --  119.50-127.00 -29.00  136
 10  ω     94.00 178.00   0.50    6.20    --  119.50 127.00  45.00  168
 11  ω     46.00 125.00   0.50    6.20    --  119.50-142.00  69.00  158
 12  ω     38.00 178.00   0.50    6.20    --  119.50   6.00-121.00  280
 13  ω     93.00 178.00   0.50    6.20    --  119.50 129.00 -45.00  170
 14  ω    -43.00  39.00   0.50    1.50    --  -40.74  38.00 -60.00  164
 15  ω      0.00  28.00   0.50    1.50    --   40.74  97.00 128.17   56
 16  ω     44.00 108.00   0.50    6.20    --  119.50-111.00 150.00  128
 17  ω     44.00 108.00   0.50    6.20    --  119.50-111.00  60.00  128
 18  ω     44.00 101.00   0.50    6.20    --  119.50-111.00   0.00  114
 19  ω     74.00 108.00   0.50    6.20    --  119.50-111.00   0.00   68
 20  ω     49.00  93.00   0.50    6.20    --  119.50 -77.00  90.00   88
 21  ω     44.00  97.00   0.50    6.20    --  119.50 -95.00   0.00  106
 22  ω     63.00 116.00   0.50    6.20    --  119.50 178.00 -90.00  106
 23  ω     42.00  68.00   0.50    6.20    --  119.50 -95.00  60.00   52
 24  ω    106.00 149.00   0.50    6.20    --  119.50 111.00  60.00   86
 25  ω     68.00  98.00   0.50    6.20    --  119.50 -95.00 120.00   60
 26  ω     96.00 129.00   0.50    6.20    --  119.50  45.00 -30.00   66
 27  ω    140.00 167.00   0.50    6.20    --  119.50  45.00 -30.00   54
 28  ω    132.00 158.00   0.50    6.20    --  119.50 111.00 150.00   52
 29  ω    118.00 156.00   0.50    6.20    --  119.50 111.00  90.00   76
 30  ω     93.00 118.00   0.50    6.20    --  119.50  77.00 150.00   50
 31  ω     64.00  98.00   0.50    6.20    --  119.50 -77.00  30.00   68
 32  ω    130.00 175.00   0.50    6.20    --  119.50 111.00-180.00   90
 33  ω    133.00 159.00   0.50    6.20    --  119.50 111.00 -30.00   52
 34  ω     42.00  67.00   0.50    6.20    --  119.50 -95.00 -30.00   50
 35  ω     79.00 104.00   0.50    6.20    --  119.50 -95.00 -30.00   50
 36  ω    107.00 177.00   0.50    6.20    --  119.50 111.00-150.00  140
 37  ω     94.00 140.00   0.50    6.20    --  119.50  61.00  30.00   92
 38  ω    144.00 170.00   0.50    6.20    --  119.50  61.00  30.00   52
 39  ω     47.00 108.00   0.50    6.20    --  119.50-111.00-120.00  122
 40  ω     93.00 156.00   0.50    6.20    --  119.50  61.00-150.00  126
 41  ω     90.00 136.00   0.50    6.20    --  119.50  77.00  60.00   92
 42  ω     44.00  78.00   0.50    6.20    --  119.50 -95.00-150.00   68
 43  ω     65.00 108.00   0.50    6.20    --  119.50-111.00 -90.00   86
 44  ω    133.00 167.00   0.50    6.20    --  119.50  77.00-150.00   68
 45  ω     63.00 103.00   0.50    6.20    --  119.50 178.00 -30.00   80
 46  ω    124.00 150.00   0.50    6.20    --  119.50  61.00 150.00   52
 47  ω     98.00 124.00   0.50    6.20    --  119.50  77.00  30.00   52
 48  ω     87.00 117.00   0.50    6.20    --  119.50  77.00 -60.00   60
 49  ω     69.00  95.00   0.50    6.20    --  119.50  15.00  30.00   52
 50  ω     73.00 105.00   0.50    6.20    --  119.50 -77.00 120.00   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      0.0077394000
_diffrn_orient_matrix_UB_12      -0.0268322000
_diffrn_orient_matrix_UB_13      -0.0474911000
_diffrn_orient_matrix_UB_21      -0.0044088000
_diffrn_orient_matrix_UB_22      0.1935323000
_diffrn_orient_matrix_UB_23      -0.0067270000
_diffrn_orient_matrix_UB_31      0.1134153000
_diffrn_orient_matrix_UB_32      0.0094327000
_diffrn_orient_matrix_UB_33      0.0029042000
_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         0.893
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                7081
_reflns_number_total             7144
_reflns_odcompleteness_completeness 95.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (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         0.758
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_coef       0.00057(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   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     592
_refine_ls_number_reflns         7144
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.091
_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)+(0.0750P)²+6.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(4)
 0.4(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 N13-C10 \\sim N13A-C10A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(N13) = Uanis(N13A)
5. Others
 Sof(N13A)=Sof(C10A)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(N13)=Sof(C10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C1B(H1B),
 C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B)
6.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
;
_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
O1A O 0.8732(3) 0.7582(5) 0.37123(14) 0.0224(8) Uani 1 1 d . . . . .
O2A O 0.7746(3) 0.7258(5) 0.31733(12) 0.0287(9) Uani 1 1 d . . . . .
O3A O 0.7457(3) 0.0508(4) 0.37769(14) 0.0241(8) Uani 1 1 d . . . . .
O4A O 0.7228(4) 0.1723(5) 0.31783(14) 0.0344(10) Uani 1 1 d . . . . .
O5A O 0.5435(3) 0.9662(5) 0.41049(14) 0.0277(9) Uani 1 1 d . . . . .
O6A O 0.5462(3) 0.9091(5) 0.34416(13) 0.0257(8) Uani 1 1 d . . . . .
O7A O 0.4338(3) 0.2904(5) 0.42038(13) 0.0211(7) Uani 1 1 d . . . . .
O8A O 0.4521(3) 0.3328(5) 0.35320(13) 0.0237(8) Uani 1 1 d . . . . .
O9A O 0.6598(3) 0.1228(4) 0.47666(12) 0.0213(7) Uani 1 1 d . . . . .
O10A O 0.5527(3) 0.2994(5) 0.50303(12) 0.0235(8) Uani 1 1 d . . . . .
N1A N 0.7736(3) 0.5346(5) 0.36839(13) 0.0173(8) Uani 1 1 d . . . . .
N2A N 0.6748(3) 0.3089(5) 0.37645(14) 0.0170(8) Uani 1 1 d . . . . .
N3A N 0.6214(3) 0.7299(5) 0.38796(13) 0.0152(8) Uani 1 1 d . . . . .
N4A N 0.5257(3) 0.5031(5) 0.39835(13) 0.0150(8) Uani 1 1 d . . . . .
N5A N 0.7396(3) 0.6441(5) 0.43874(13) 0.0151(8) Uani 1 1 d . . . . .
N6A N 0.6397(3) 0.3786(5) 0.44772(13) 0.0160(8) Uani 1 1 d . . . . .
N7A N 0.8091(3) 0.6835(5) 0.35119(14) 0.0184(8) Uani 1 1 d . . . . .
N8A N 0.7199(3) 0.1666(6) 0.35532(15) 0.0226(9) Uani 1 1 d . . . . .
N9A N 0.5634(3) 0.8807(5) 0.38069(15) 0.0189(9) Uani 1 1 d . . . . .
N10A N 0.4673(3) 0.3643(5) 0.38991(13) 0.0158(8) Uani 1 1 d . . . . .
N11A N 0.8539(3) 0.8502(6) 0.47305(15) 0.0244(9) Uani 1 1 d . . . . .
N12A N 0.6159(3) 0.2569(5) 0.47759(14) 0.0173(8) Uani 1 1 d . . . . .
C1A C 0.6788(3) 0.4665(6) 0.35317(16) 0.0168(9) Uani 1 1 d . . . . .
H1A H 0.680783 0.445240 0.322433 0.020 Uiso 1 1 calc R U . . .
C2A C 0.5861(4) 0.5811(6) 0.36578(16) 0.0176(9) Uani 1 1 d . . . . .
H2A H 0.545700 0.612879 0.340878 0.021 Uiso 1 1 calc R U . . .
C3A C 0.7816(3) 0.5087(6) 0.41350(15) 0.0145(9) Uani 1 1 d . . . . .
H3A H 0.851704 0.486660 0.421652 0.017 Uiso 1 1 calc R U . . .
C4A C 0.7175(3) 0.3432(6) 0.41864(15) 0.0149(9) Uani 1 1 d . . . . .
H4A H 0.758911 0.245741 0.428331 0.018 Uiso 1 1 calc R U . . .
C5A C 0.6370(3) 0.6833(6) 0.43212(15) 0.0142(9) Uani 1 1 d . . . . .
H5A H 0.614653 0.776223 0.451151 0.017 Uiso 1 1 calc R U . . .
C6A C 0.5744(3) 0.5176(6) 0.43898(15) 0.0148(9) Uani 1 1 d . . . . .
H6A H 0.525030 0.533172 0.461860 0.018 Uiso 1 1 calc R U . . .
C7A C 0.8010(4) 0.7562(6) 0.45643(16) 0.0152(9) Uani 1 1 d . . . . .
O1B O 0.4862(3) 0.0474(5) 0.62520(14) 0.0231(8) Uani 1 1 d . . . . .
O2B O 0.4634(4) 0.1760(5) 0.68456(13) 0.0340(10) Uani 1 1 d . . . . .
O3B O 0.6128(3) 0.7578(5) 0.62331(15) 0.0245(8) Uani 1 1 d . . . . .
O4B O 0.5264(3) 0.7230(5) 0.68013(13) 0.0296(9) Uani 1 1 d . . . . .
O5B O 0.1679(3) 0.2909(5) 0.58474(13) 0.0237(8) Uani 1 1 d . . . . .
O6B O 0.1925(3) 0.3365(5) 0.65123(13) 0.0262(8) Uani 1 1 d . . . . .
O7B O 0.2909(3) 0.9680(5) 0.58880(14) 0.0241(8) Uani 1 1 d . . . . .
O8B O 0.2858(3) 0.9069(5) 0.65531(13) 0.0244(8) Uani 1 1 d . . . . .
O9B O 0.6193(3) 0.7078(5) 0.53169(14) 0.0290(9) Uani 1 1 d . . . . .
O10B O 0.4975(3) 0.8874(5) 0.53138(17) 0.0371(10) Uani 1 1 d . . . . .
N1B N 0.4163(3) 0.3060(5) 0.62565(14) 0.0166(8) Uani 1 1 d . . . . .
N2B N 0.5149(3) 0.5340(5) 0.62996(14) 0.0172(8) Uani 1 1 d . . . . .
N3B N 0.2660(3) 0.4996(5) 0.60405(14) 0.0159(8) Uani 1 1 d . . . . .
N5B N 0.3739(3) 0.3626(5) 0.55376(13) 0.0160(8) Uani 1 1 d . . . . .
N6B N 0.4751(3) 0.6299(5) 0.55935(14) 0.0169(8) Uani 1 1 d . . . . .
N7B N 0.4611(3) 0.1667(5) 0.64694(15) 0.0189(8) Uani 1 1 d . . . . .
N8B N 0.5529(3) 0.6847(5) 0.64592(14) 0.0190(8) Uani 1 1 d . . . . .
N9B N 0.2053(3) 0.3643(5) 0.61443(14) 0.0175(8) Uani 1 1 d . . . . .
N4B N 0.3621(3) 0.7256(5) 0.61173(13) 0.0161(8) Uani 1 1 d . . . . .
N11B N 0.3264(4) 0.1400(6) 0.50244(16) 0.0267(10) Uani 1 1 d . . . . .
N12B N 0.5343(3) 0.7509(6) 0.53986(15) 0.0228(10) Uani 1 1 d . . . . .
N10B N 0.3057(3) 0.8773(5) 0.61892(15) 0.0197(8) Uani 1 1 d . . . . .
C1B C 0.4220(3) 0.4684(6) 0.64760(16) 0.0165(9) Uani 1 1 d . . . . .
H1B H 0.427110 0.451982 0.678445 0.020 Uiso 1 1 calc R U . . .
C2B C 0.3286(3) 0.5790(6) 0.63565(15) 0.0157(9) Uani 1 1 d . . . . .
H2B H 0.289872 0.613447 0.660829 0.019 Uiso 1 1 calc R U . . .
C3B C 0.4543(3) 0.3351(6) 0.58222(15) 0.0169(9) Uani 1 1 d . . . . .
H3B H 0.495245 0.236396 0.572918 0.020 Uiso 1 1 calc R U . . .
C4B C 0.5195(4) 0.4989(6) 0.58549(16) 0.0170(9) Uani 1 1 d . . . . .
H4B H 0.588949 0.475138 0.576576 0.020 Uiso 1 1 calc R U . . .
C5B C 0.3104(3) 0.5068(6) 0.56274(16) 0.0167(9) Uani 1 1 d . . . . .
H5B H 0.258679 0.520324 0.540726 0.020 Uiso 1 1 calc R U . . .
C6B C 0.3729(3) 0.6738(6) 0.56759(16) 0.0159(9) Uani 1 1 d . . . . .
H6B H 0.349200 0.764587 0.548246 0.019 Uiso 1 1 calc R U . . .
C7B C 0.3468(4) 0.2428(6) 0.52651(16) 0.0179(9) Uani 1 1 d . . . . .
N12 N 0.4997(8) 0.4260(13) 0.7714(2) 0.070(2) Uani 1 1 d . . . . .
N13 N 0.2488(9) 0.5905(17) 0.7310(3) 0.063(3) Uani 0.731(11) 1 d D . P A 1
C8 C 0.5773(7) 0.4282(12) 0.7558(2) 0.0499(19) Uani 1 1 d . . . . .
C9 C 0.6747(7) 0.4350(14) 0.7359(2) 0.057(2) Uani 1 1 d . . . . .
H9A H 0.666815 0.430678 0.705543 0.085 Uiso 1 1 calc R U . . .
H9B H 0.714380 0.338013 0.745158 0.085 Uiso 1 1 calc R U . . .
H9C H 0.707943 0.540805 0.743720 0.085 Uiso 1 1 calc R U . . .
C10 C 0.1666(9) 0.5803(17) 0.7466(3) 0.050(3) Uani 0.731(11) 1 d D . P A 1
C11 C 0.0698(10) 0.5709(17) 0.7659(3) 0.042(2) Uani 0.731(11) 1 d D . P A 1
H11A H 0.022281 0.524288 0.745900 0.063 Uiso 0.731(11) 1 calc R U P A 1
H11B H 0.048802 0.684816 0.774370 0.063 Uiso 0.731(11) 1 calc R U P A 1
H11C H 0.073048 0.497072 0.790471 0.063 Uiso 0.731(11) 1 calc R U P A 1
N13A N -0.055(2) 0.602(4) 0.7586(8) 0.063(3) Uani 0.269(11) 1 d D . P A 2
C10A C 0.036(2) 0.579(6) 0.7603(14) 0.050(3) Uani 0.269(11) 1 d D . P A 2
C11A C 0.137(2) 0.564(4) 0.7707(9) 0.042(2) Uani 0.269(11) 1 d D . P A 2
H11D H 0.177271 0.571014 0.745250 0.063 Uiso 0.269(11) 1 calc R U P A 2
H11E H 0.148807 0.454310 0.784295 0.063 Uiso 0.269(11) 1 calc R U P A 2
H11F H 0.156061 0.655909 0.789698 0.063 Uiso 0.269(11) 1 calc R U P A 2


_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 N7A 1.229(6) . ?
O2A N7A 1.228(6) . ?
O3A N8A 1.212(7) . ?
O4A N8A 1.204(7) . ?
O5A N9A 1.200(6) . ?
O6A N9A 1.215(6) . ?
O7A N10A 1.225(6) . ?
O8A N10A 1.221(6) . ?
O9A N12A 1.212(6) . ?
O10A N12A 1.229(6) . ?
N1A N7A 1.383(6) . ?
N1A C1A 1.474(6) . ?
N1A C3A 1.465(6) . ?
N2A N8A 1.445(6) . ?
N2A C1A 1.450(6) . ?
N2A C4A 1.496(6) . ?
N3A N9A 1.442(5) . ?
N3A C2A 1.451(6) . ?
N3A C5A 1.478(6) . ?
N4A N10A 1.376(6) . ?
N4A C2A 1.462(6) . ?
N4A C6A 1.464(6) . ?
N5A C3A 1.454(6) . ?
N5A C5A 1.439(6) . ?
N5A C7A 1.339(6) . ?
N6A N12A 1.393(6) . ?
N6A C4A 1.434(6) . ?
N6A C6A 1.435(6) . ?
N11A C7A 1.159(7) . ?
C1A H1A 1.0000 . ?
C1A C2A 1.598(7) . ?
C2A H2A 1.0000 . ?
C3A H3A 1.0000 . ?
C3A C4A 1.574(6) . ?
C4A H4A 1.0000 . ?
C5A H5A 1.0000 . ?
C5A C6A 1.571(6) . ?
C6A H6A 1.0000 . ?
O1B N7B 1.218(6) . ?
O2B N7B 1.209(6) . ?
O3B N8B 1.231(6) . ?
O4B N8B 1.193(6) . ?
O5B N9B 1.224(6) . ?
O6B N9B 1.213(6) . ?
O7B N10B 1.218(6) . ?
O8B N10B 1.220(6) . ?
O9B N12B 1.228(6) . ?
O10B N12B 1.216(6) . ?
N1B N7B 1.428(6) . ?
N1B C1B 1.462(6) . ?
N1B C3B 1.502(7) . ?
N2B N8B 1.391(6) . ?
N2B C1B 1.473(6) . ?
N2B C4B 1.454(7) . ?
N3B N9B 1.385(6) . ?
N3B C2B 1.461(6) . ?
N3B C5B 1.456(6) . ?
N5B C3B 1.437(6) . ?
N5B C5B 1.453(6) . ?
N5B C7B 1.337(7) . ?
N6B N12B 1.393(6) . ?
N6B C4B 1.459(6) . ?
N6B C6B 1.449(6) . ?
N4B N10B 1.437(6) . ?
N4B C2B 1.459(6) . ?
N4B C6B 1.480(6) . ?
N11B C7B 1.152(7) . ?
C1B H1B 1.0000 . ?
C1B C2B 1.583(7) . ?
C2B H2B 1.0000 . ?
C3B H3B 1.0000 . ?
C3B C4B 1.567(7) . ?
C4B H4B 1.0000 . ?
C5B H5B 1.0000 . ?
C5B C6B 1.572(6) . ?
C6B H6B 1.0000 . ?
N12 C8 1.163(13) . ?
N13 C10 1.223(16) . ?
C8 C9 1.465(12) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.450(17) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N13A C10A 1.25(3) . ?
C10A C11A 1.41(3) . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?

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
N7A N1A C1A 118.6(4) . . ?
N7A N1A C3A 119.1(4) . . ?
C3A N1A C1A 109.9(4) . . ?
N8A N2A C1A 114.0(4) . . ?
N8A N2A C4A 113.6(4) . . ?
C1A N2A C4A 107.2(4) . . ?
N9A N3A C2A 114.0(4) . . ?
N9A N3A C5A 115.9(4) . . ?
C2A N3A C5A 108.4(4) . . ?
N10A N4A C2A 121.0(4) . . ?
N10A N4A C6A 119.7(4) . . ?
C2A N4A C6A 110.5(4) . . ?
C5A N5A C3A 116.9(4) . . ?
C7A N5A C3A 118.5(4) . . ?
C7A N5A C5A 121.4(4) . . ?
N12A N6A C4A 118.9(4) . . ?
N12A N6A C6A 121.2(4) . . ?
C4A N6A C6A 118.3(4) . . ?
O1A N7A N1A 116.3(4) . . ?
O2A N7A O1A 126.9(4) . . ?
O2A N7A N1A 116.8(4) . . ?
O3A N8A N2A 115.4(5) . . ?
O4A N8A O3A 127.5(5) . . ?
O4A N8A N2A 117.0(5) . . ?
O5A N9A O6A 128.4(4) . . ?
O5A N9A N3A 117.1(4) . . ?
O6A N9A N3A 114.3(4) . . ?
O7A N10A N4A 115.7(4) . . ?
O8A N10A O7A 127.6(4) . . ?
O8A N10A N4A 116.6(4) . . ?
O9A N12A O10A 126.5(4) . . ?
O9A N12A N6A 118.0(4) . . ?
O10A N12A N6A 115.4(4) . . ?
N1A C1A H1A 111.4 . . ?
N1A C1A C2A 113.2(4) . . ?
N2A C1A N1A 100.0(4) . . ?
N2A C1A H1A 111.4 . . ?
N2A C1A C2A 108.9(4) . . ?
C2A C1A H1A 111.4 . . ?
N3A C2A N4A 100.0(4) . . ?
N3A C2A C1A 108.8(4) . . ?
N3A C2A H2A 111.7 . . ?
N4A C2A C1A 112.5(4) . . ?
N4A C2A H2A 111.7 . . ?
C1A C2A H2A 111.7 . . ?
N1A C3A H3A 110.6 . . ?
N1A C3A C4A 100.3(4) . . ?
N5A C3A N1A 114.7(4) . . ?
N5A C3A H3A 110.6 . . ?
N5A C3A C4A 109.5(4) . . ?
C4A C3A H3A 110.6 . . ?
N2A C4A C3A 105.5(4) . . ?
N2A C4A H4A 111.1 . . ?
N6A C4A N2A 109.8(4) . . ?
N6A C4A C3A 108.2(4) . . ?
N6A C4A H4A 111.1 . . ?
C3A C4A H4A 111.1 . . ?
N3A C5A H5A 111.1 . . ?
N3A C5A C6A 105.2(4) . . ?
N5A C5A N3A 109.4(4) . . ?
N5A C5A H5A 111.1 . . ?
N5A C5A C6A 108.8(4) . . ?
C6A C5A H5A 111.1 . . ?
N4A C6A C5A 100.6(4) . . ?
N4A C6A H6A 111.2 . . ?
N6A C6A N4A 113.0(4) . . ?
N6A C6A C5A 109.2(4) . . ?
N6A C6A H6A 111.2 . . ?
C5A C6A H6A 111.2 . . ?
N11A C7A N5A 177.6(6) . . ?
N7B N1B C1B 114.9(4) . . ?
N7B N1B C3B 114.5(4) . . ?
C1B N1B C3B 107.2(4) . . ?
N8B N2B C1B 118.3(4) . . ?
N8B N2B C4B 120.5(4) . . ?
C4B N2B C1B 110.3(4) . . ?
N9B N3B C2B 120.4(4) . . ?
N9B N3B C5B 119.6(4) . . ?
C5B N3B C2B 112.0(4) . . ?
C3B N5B C5B 116.1(4) . . ?
C7B N5B C3B 121.1(4) . . ?
C7B N5B C5B 121.3(4) . . ?
N12B N6B C4B 120.3(4) . . ?
N12B N6B C6B 117.9(4) . . ?
C6B N6B C4B 117.2(4) . . ?
O1B N7B N1B 115.9(4) . . ?
O2B N7B O1B 127.7(5) . . ?
O2B N7B N1B 116.2(4) . . ?
O3B N8B N2B 115.2(4) . . ?
O4B N8B O3B 128.4(4) . . ?
O4B N8B N2B 116.3(4) . . ?
O5B N9B N3B 115.0(4) . . ?
O6B N9B O5B 127.8(4) . . ?
O6B N9B N3B 117.2(4) . . ?
N10B N4B C2B 114.1(4) . . ?
N10B N4B C6B 115.8(4) . . ?
C2B N4B C6B 108.4(4) . . ?
O9B N12B N6B 116.5(4) . . ?
O10B N12B O9B 125.5(5) . . ?
O10B N12B N6B 118.0(4) . . ?
O7B N10B O8B 127.6(5) . . ?
O7B N10B N4B 116.6(4) . . ?
O8B N10B N4B 115.4(4) . . ?
N1B C1B N2B 99.6(4) . . ?
N1B C1B H1B 111.5 . . ?
N1B C1B C2B 108.8(4) . . ?
N2B C1B H1B 111.5 . . ?
N2B C1B C2B 113.4(4) . . ?
C2B C1B H1B 111.5 . . ?
N3B C2B C1B 113.3(4) . . ?
N3B C2B H2B 111.9 . . ?
N4B C2B N3B 98.9(4) . . ?
N4B C2B C1B 108.3(4) . . ?
N4B C2B H2B 111.9 . . ?
C1B C2B H2B 111.9 . . ?
N1B C3B H3B 110.3 . . ?
N1B C3B C4B 104.8(4) . . ?
N5B C3B N1B 110.6(4) . . ?
N5B C3B H3B 110.3 . . ?
N5B C3B C4B 110.2(4) . . ?
C4B C3B H3B 110.3 . . ?
N2B C4B N6B 114.3(4) . . ?
N2B C4B C3B 101.4(4) . . ?
N2B C4B H4B 110.9 . . ?
N6B C4B C3B 108.1(4) . . ?
N6B C4B H4B 110.9 . . ?
C3B C4B H4B 110.9 . . ?
N3B C5B H5B 110.9 . . ?
N3B C5B C6B 99.5(4) . . ?
N5B C5B N3B 113.2(4) . . ?
N5B C5B H5B 110.9 . . ?
N5B C5B C6B 110.8(4) . . ?
C6B C5B H5B 110.9 . . ?
N6B C6B N4B 109.5(4) . . ?
N6B C6B C5B 107.2(4) . . ?
N6B C6B H6B 111.3 . . ?
N4B C6B C5B 105.8(4) . . ?
N4B C6B H6B 111.3 . . ?
C5B C6B H6B 111.3 . . ?
N11B C7B N5B 177.9(6) . . ?
N12 C8 C9 178.7(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N13 C10 C11 178.7(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N13A C10A C11A 168(5) . . ?
C10A C11A H11D 109.5 . . ?
C10A C11A H11E 109.5 . . ?
C10A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1A C1A C2A N3A 2.5(5) . . . . ?
N1A C1A C2A N4A -107.3(5) . . . . ?
N1A C3A C4A N2A -5.2(4) . . . . ?
N1A C3A C4A N6A -122.7(4) . . . . ?
N2A C1A C2A N3A 112.8(4) . . . . ?
N2A C1A C2A N4A 3.0(5) . . . . ?
N3A C5A C6A N4A -4.5(4) . . . . ?
N3A C5A C6A N6A 114.5(4) . . . . ?
N5A C3A C4A N2A 115.8(4) . . . . ?
N5A C3A C4A N6A -1.7(5) . . . . ?
N5A C5A C6A N4A -121.7(4) . . . . ?
N5A C5A C6A N6A -2.7(5) . . . . ?
N7A N1A C1A N2A 175.7(4) . . . . ?
N7A N1A C1A C2A -68.6(5) . . . . ?
N7A N1A C3A N5A 53.8(6) . . . . ?
N7A N1A C3A C4A 171.1(4) . . . . ?
N8A N2A C1A N1A -89.9(4) . . . . ?
N8A N2A C1A C2A 151.2(4) . . . . ?
N8A N2A C4A N6A -137.0(4) . . . . ?
N8A N2A C4A C3A 106.6(4) . . . . ?
N9A N3A C2A N4A -95.5(4) . . . . ?
N9A N3A C2A C1A 146.4(4) . . . . ?
N9A N3A C5A N5A -133.2(4) . . . . ?
N9A N3A C5A C6A 110.1(4) . . . . ?
N10A N4A C2A N3A 172.7(4) . . . . ?
N10A N4A C2A C1A -72.0(5) . . . . ?
N10A N4A C6A N6A 59.3(5) . . . . ?
N10A N4A C6A C5A 175.6(4) . . . . ?
N12A N6A C4A N2A 107.3(5) . . . . ?
N12A N6A C4A C3A -138.0(4) . . . . ?
N12A N6A C6A N4A -108.6(5) . . . . ?
N12A N6A C6A C5A 140.3(4) . . . . ?
C1A N1A N7A O1A 162.2(4) . . . . ?
C1A N1A N7A O2A -18.9(6) . . . . ?
C1A N1A C3A N5A -87.9(5) . . . . ?
C1A N1A C3A C4A 29.3(4) . . . . ?
C1A N2A N8A O3A 157.8(4) . . . . ?
C1A N2A N8A O4A -26.1(6) . . . . ?
C1A N2A C4A N6A 96.1(4) . . . . ?
C1A N2A C4A C3A -20.3(5) . . . . ?
C2A N3A N9A O5A 136.0(4) . . . . ?
C2A N3A N9A O6A -48.3(5) . . . . ?
C2A N3A C5A N5A 97.1(4) . . . . ?
C2A N3A C5A C6A -19.6(5) . . . . ?
C2A N4A N10A O7A 167.4(4) . . . . ?
C2A N4A N10A O8A -15.1(6) . . . . ?
C2A N4A C6A N6A -88.6(5) . . . . ?
C2A N4A C6A C5A 27.7(5) . . . . ?
C3A N1A N7A O1A 23.7(6) . . . . ?
C3A N1A N7A O2A -157.3(4) . . . . ?
C3A N1A C1A N2A -42.3(5) . . . . ?
C3A N1A C1A C2A 73.3(5) . . . . ?
C3A N5A C5A N3A -58.0(5) . . . . ?
C3A N5A C5A C6A 56.5(5) . . . . ?
C4A N2A N8A O3A 34.5(6) . . . . ?
C4A N2A N8A O4A -149.3(5) . . . . ?
C4A N2A C1A N1A 36.8(4) . . . . ?
C4A N2A C1A C2A -82.2(4) . . . . ?
C4A N6A N12A O9A -2.8(6) . . . . ?
C4A N6A N12A O10A 175.9(4) . . . . ?
C4A N6A C6A N4A 56.4(6) . . . . ?
C4A N6A C6A C5A -54.6(5) . . . . ?
C5A N3A N9A O5A 9.0(6) . . . . ?
C5A N3A N9A O6A -175.2(4) . . . . ?
C5A N3A C2A N4A 35.2(5) . . . . ?
C5A N3A C2A C1A -82.8(4) . . . . ?
C5A N5A C3A N1A 57.5(5) . . . . ?
C5A N5A C3A C4A -54.3(5) . . . . ?
C6A N4A N10A O7A 22.9(6) . . . . ?
C6A N4A N10A O8A -159.6(4) . . . . ?
C6A N4A C2A N3A -39.9(5) . . . . ?
C6A N4A C2A C1A 75.4(5) . . . . ?
C6A N6A N12A O9A 162.1(4) . . . . ?
C6A N6A N12A O10A -19.2(7) . . . . ?
C6A N6A C4A N2A -58.1(5) . . . . ?
C6A N6A C4A C3A 56.6(5) . . . . ?
C7A N5A C3A N1A -102.5(5) . . . . ?
C7A N5A C3A C4A 145.7(4) . . . . ?
C7A N5A C5A N3A 101.3(5) . . . . ?
C7A N5A C5A C6A -144.2(4) . . . . ?
N1B C1B C2B N3B -4.6(6) . . . . ?
N1B C1B C2B N4B -113.3(4) . . . . ?
N1B C3B C4B N2B 3.4(4) . . . . ?
N1B C3B C4B N6B -117.2(4) . . . . ?
N2B C1B C2B N3B 105.3(5) . . . . ?
N2B C1B C2B N4B -3.4(6) . . . . ?
N3B C5B C6B N6B 122.2(4) . . . . ?
N3B C5B C6B N4B 5.3(4) . . . . ?
N5B C3B C4B N2B 122.4(4) . . . . ?
N5B C3B C4B N6B 1.9(5) . . . . ?
N5B C5B C6B N6B 2.8(5) . . . . ?
N5B C5B C6B N4B -114.1(4) . . . . ?
N7B N1B C1B N2B 91.3(4) . . . . ?
N7B N1B C1B C2B -149.8(4) . . . . ?
N7B N1B C3B N5B 134.3(4) . . . . ?
N7B N1B C3B C4B -106.9(4) . . . . ?
N8B N2B C1B N1B -174.2(4) . . . . ?
N8B N2B C1B C2B 70.3(6) . . . . ?
N8B N2B C4B N6B -55.2(6) . . . . ?
N8B N2B C4B C3B -171.3(4) . . . . ?
N9B N3B C2B N4B -170.8(4) . . . . ?
N9B N3B C2B C1B 74.8(5) . . . . ?
N9B N3B C5B N5B -60.2(5) . . . . ?
N9B N3B C5B C6B -177.8(4) . . . . ?
N12B N6B C4B N2B 99.3(5) . . . . ?
N12B N6B C4B C3B -148.6(4) . . . . ?
N12B N6B C6B N4B -99.7(5) . . . . ?
N12B N6B C6B C5B 145.9(4) . . . . ?
N10B N4B C2B N3B 96.1(4) . . . . ?
N10B N4B C2B C1B -145.7(4) . . . . ?
N10B N4B C6B N6B 134.0(4) . . . . ?
N10B N4B C6B C5B -110.7(4) . . . . ?
C1B N1B N7B O1B -157.1(4) . . . . ?
C1B N1B N7B O2B 27.8(6) . . . . ?
C1B N1B C3B N5B -97.0(4) . . . . ?
C1B N1B C3B C4B 21.7(5) . . . . ?
C1B N2B N8B O3B -160.5(4) . . . . ?
C1B N2B N8B O4B 22.2(6) . . . . ?
C1B N2B C4B N6B 88.2(5) . . . . ?
C1B N2B C4B C3B -27.9(5) . . . . ?
C2B N3B N9B O5B -169.2(4) . . . . ?
C2B N3B N9B O6B 13.4(6) . . . . ?
C2B N3B C5B N5B 88.8(5) . . . . ?
C2B N3B C5B C6B -28.9(5) . . . . ?
C2B N4B N10B O7B -142.5(4) . . . . ?
C2B N4B N10B O8B 43.7(5) . . . . ?
C2B N4B C6B N6B -96.4(4) . . . . ?
C2B N4B C6B C5B 18.9(5) . . . . ?
C3B N1B N7B O1B -32.5(5) . . . . ?
C3B N1B N7B O2B 152.5(5) . . . . ?
C3B N1B C1B N2B -37.1(4) . . . . ?
C3B N1B C1B C2B 81.7(4) . . . . ?
C3B N5B C5B N3B -57.4(5) . . . . ?
C3B N5B C5B C6B 53.4(6) . . . . ?
C4B N2B N8B O3B -19.9(6) . . . . ?
C4B N2B N8B O4B 162.8(4) . . . . ?
C4B N2B C1B N1B 41.4(5) . . . . ?
C4B N2B C1B C2B -74.1(5) . . . . ?
C4B N6B N12B O9B 27.8(7) . . . . ?
C4B N6B N12B O10B -154.1(5) . . . . ?
C4B N6B C6B N4B 56.2(5) . . . . ?
C4B N6B C6B C5B -58.2(5) . . . . ?
C5B N3B N9B O5B -22.8(6) . . . . ?
C5B N3B N9B O6B 159.8(4) . . . . ?
C5B N3B C2B N4B 40.6(5) . . . . ?
C5B N3B C2B C1B -73.9(5) . . . . ?
C5B N5B C3B N1B 59.8(5) . . . . ?
C5B N5B C3B C4B -55.6(5) . . . . ?
C6B N6B N12B O9B -177.1(5) . . . . ?
C6B N6B N12B O10B 1.1(7) . . . . ?
C6B N6B C4B N2B -56.0(5) . . . . ?
C6B N6B C4B C3B 56.1(5) . . . . ?
C6B N4B N10B O7B -15.7(6) . . . . ?
C6B N4B N10B O8B 170.6(4) . . . . ?
C6B N4B C2B N3B -34.5(4) . . . . ?
C6B N4B C2B C1B 83.8(5) . . . . ?
C7B N5B C3B N1B -106.2(5) . . . . ?
C7B N5B C3B C4B 138.4(5) . . . . ?
C7B N5B C5B N3B 108.5(5) . . . . ?
C7B N5B C5B C6B -140.7(5) . . . . ?

_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.845
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(4)
2 0.4(4)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
