#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/72/7227234.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7227234
loop_
_publ_author_name
'Sato, M.'
'Takeda, T.'
'Hoshino, N.'
'Akutagawa, T.'
_publ_section_title
;
 Electronic and crystal structures of 1,2,3-triazole-fused p-benzoquinone
 derivatives
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              910
_journal_paper_doi               10.1039/C6CE02167K
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C18 H32 N8 O2'
_chemical_formula_sum            'C18 H32 N8 O2'
_chemical_formula_weight         392.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-09-24 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                102.0567(14)
_cell_angle_beta                 102.4887(18)
_cell_angle_gamma                101.2122(18)
_cell_formula_units_Z            1
_cell_length_a                   7.5718(3)
_cell_length_b                   8.46267(18)
_cell_length_c                   8.7904(2)
_cell_measurement_reflns_used    2712
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      5.34
_cell_volume                     520.60(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5687
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.220
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         5.341
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             212.00
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0811P)²+0.0409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                1492
_reflns_number_total             1866
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c6ce02167k2.cif
_cod_data_source_block           BTABQ-DiPA
_cod_depositor_comments
'Adding full bibliography for 7227231--7227238.cif.'
_cod_database_code               7227234
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
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_multiplicity
_atom_site_calc_flag
O1 O 0.21285(18) 0.77816(15) 0.43036(15) 0.0309(4) Uani 1 2 d
N1 N 0.2960(2) 1.01997(19) 0.74792(18) 0.0283(4) Uani 1 2 d
N2 N 0.2793(2) 1.14644(18) 0.86225(17) 0.0289(4) Uani 1 2 d
N3 N 0.1327(2) 1.20582(19) 0.80852(17) 0.0293(4) Uani 1 2 d
N4 N 0.4414(2) 0.74952(19) 0.83676(18) 0.0261(4) Uani 1 2 d
C1 C 0.1159(3) 0.8747(2) 0.4593(2) 0.0260(5) Uani 1 2 d
C2 C 0.1557(3) 0.9985(2) 0.6165(2) 0.0242(4) Uani 1 2 d
C3 C -0.0530(3) 0.8862(2) 0.3462(2) 0.0254(4) Uani 1 2 d
C4 C 0.5221(3) 0.6645(2) 0.7091(2) 0.0283(5) Uani 1 2 d
C5 C 0.6738(3) 0.7965(3) 0.6861(3) 0.0393(5) Uani 1 2 d
C6 C 0.5951(4) 0.5233(3) 0.7594(3) 0.0345(5) Uani 1 2 d
C7 C 0.2770(3) 0.6453(2) 0.8714(2) 0.0284(5) Uani 1 2 d
C8 C 0.1143(3) 0.5756(3) 0.7216(3) 0.0351(5) Uani 1 2 d
C9 C 0.2263(3) 0.7534(3) 1.0086(3) 0.0362(5) Uani 1 2 d
H4 H 0.414(3) 0.620(2) 0.609(2) 0.023(5) Uiso 1 2 d
H5A H 0.780(4) 0.839(3) 0.789(3) 0.057(7) Uiso 1 2 d
H5B H 0.732(3) 0.747(3) 0.603(3) 0.044(6) Uiso 1 2 d
H5C H 0.626(3) 0.891(3) 0.659(3) 0.052(7) Uiso 1 2 d
H6A H 0.691(3) 0.565(3) 0.862(3) 0.038(6) Uiso 1 2 d
H6B H 0.498(3) 0.433(3) 0.766(3) 0.043(6) Uiso 1 2 d
H6C H 0.659(3) 0.472(3) 0.679(2) 0.039(6) Uiso 1 2 d
H7 H 0.321(3) 0.552(2) 0.910(2) 0.028(5) Uiso 1 2 d
H8A H 0.014(3) 0.510(3) 0.743(2) 0.043(6) Uiso 1 2 d
H8B H 0.066(3) 0.668(3) 0.685(3) 0.051(7) Uiso 1 2 d
H8C H 0.150(3) 0.500(3) 0.630(3) 0.051(7) Uiso 1 2 d
H9A H 0.184(3) 0.840(3) 0.975(3) 0.045(6) Uiso 1 2 d
H9B H 0.121(3) 0.687(3) 1.040(3) 0.054(7) Uiso 1 2 d
H9C H 0.333(3) 0.796(3) 1.106(3) 0.049(6) Uiso 1 2 d
H4A H 0.543(3) 0.794(3) 0.942(3) 0.039(6) Uiso 1 2 d
H4B H 0.406(3) 0.843(3) 0.808(3) 0.050(7) Uiso 1 2 d
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 N1 C2 106.26(16) yes . .
N1 N2 N3 111.87(13) yes . .
N2 N3 C3 105.62(15) yes . 2_576
C4 N4 C7 117.23(13) yes . .
O1 C1 C2 123.49(16) yes . .
O1 C1 C3 125.94(15) yes . .
C2 C1 C3 110.58(17) yes . .
N1 C2 C1 126.49(18) yes . .
N1 C2 C3 107.87(15) yes . 2_576
C1 C2 C3 125.64(16) yes . 2_576
N3 C3 C1 127.84(18) yes 2_576 .
N3 C3 C2 108.38(16) yes 2_576 2_576
C1 C3 C2 123.76(15) yes . 2_576
N4 C4 C5 107.53(15) yes . .
N4 C4 C6 109.98(17) yes . .
C5 C4 C6 112.5(2) yes . .
N4 C7 C8 111.09(17) yes . .
N4 C7 C9 108.00(15) yes . .
C8 C7 C9 112.14(19) yes . .
C4 N4 H4A 108.6(15) no . .
C4 N4 H4B 108.8(15) no . .
C7 N4 H4A 106.8(14) no . .
C7 N4 H4B 108.2(15) no . .
H4A N4 H4B 106.7(17) no . .
N4 C4 H4 104.7(13) no . .
C5 C4 H4 111.0(12) no . .
C6 C4 H4 110.8(11) no . .
C4 C5 H5A 109.0(16) no . .
C4 C5 H5B 110.8(13) no . .
C4 C5 H5C 111.8(14) no . .
H5A C5 H5B 104(2) no . .
H5A C5 H5C 109.7(19) no . .
H5B C5 H5C 111(2) no . .
C4 C6 H6A 110.7(14) no . .
C4 C6 H6B 113.6(16) no . .
C4 C6 H6C 110.5(13) no . .
H6A C6 H6B 109.8(19) no . .
H6A C6 H6C 105.3(19) no . .
H6B C6 H6C 106.6(18) no . .
N4 C7 H7 106.7(12) no . .
C8 C7 H7 110.5(9) no . .
C9 C7 H7 108.2(12) no . .
C7 C8 H8A 110.8(13) no . .
C7 C8 H8B 111.0(10) no . .
C7 C8 H8C 111.3(13) no . .
H8A C8 H8B 105(2) no . .
H8A C8 H8C 106.7(19) no . .
H8B C8 H8C 111(2) no . .
C7 C9 H9A 109.7(15) no . .
C7 C9 H9B 110.7(13) no . .
C7 C9 H9C 111.1(16) no . .
H9A C9 H9B 107(2) no . .
H9A C9 H9C 111.8(19) no . .
H9B C9 H9C 107(2) no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
O1 C1 1.224(3) yes .
N1 N2 1.353(2) yes .
N1 C2 1.343(2) yes .
N2 N3 1.340(2) yes .
N3 C3 1.356(2) yes 2_576
N4 C4 1.510(3) yes .
N4 C7 1.507(3) yes .
C1 C2 1.480(2) yes .
C1 C3 1.474(3) yes .
C2 C3 1.391(3) yes 2_576
C4 C5 1.518(3) yes .
C4 C6 1.517(3) yes .
C7 C8 1.514(3) yes .
C7 C9 1.521(3) yes .
N4 H4A 1.010(19) no .
N4 H4B 0.94(3) no .
C4 H4 1.008(17) no .
C5 H5A 1.01(2) no .
C5 H5B 0.99(3) no .
C5 H5C 0.99(3) no .
C6 H6A 0.97(2) no .
C6 H6B 0.97(2) no .
C6 H6C 1.02(2) no .
C7 H7 1.01(2) no .
C8 H8A 0.93(2) no .
C8 H8B 1.01(3) no .
C8 H8C 1.04(3) no .
C9 H9A 0.93(3) no .
C9 H9B 1.01(3) no .
C9 H9C 0.99(2) no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
O1 N1 2.9545(18) no .
O1 N3 3.026(2) no 2_576
N2 C1 3.600(2) no .
N2 C1 3.591(2) no 2_576
C1 C1 3.073(3) no 2_576
C2 C2 2.777(3) no 2_576
C3 C3 2.820(2) no 2_576
C4 C8 3.064(3) no .
C6 C7 3.067(4) no .
O1 C4 3.434(2) no .
O1 C6 3.481(3) no 2_666
O1 C8 3.494(3) no .
O1 C8 3.301(2) no 2_566
N1 N4 2.901(3) no .
N1 C7 3.546(3) no .
N1 C9 3.583(3) no .
N2 N4 2.8514(19) no 2_677
N2 C7 3.528(2) no 2_677
N2 C9 3.543(3) no 2_677
N3 C7 3.554(2) no 1_565
N3 C8 3.394(3) no 1_565
N3 C9 3.481(3) no 2_577
N4 N1 2.901(3) no .
N4 N2 2.8514(19) no 2_677
C1 C5 3.544(3) no 2_676
C4 O1 3.434(2) no .
C5 C1 3.544(3) no 2_676
C6 O1 3.481(3) no 2_666
C7 N1 3.546(3) no .
C7 N2 3.528(2) no 2_677
C7 N3 3.554(2) no 1_545
C8 O1 3.494(3) no .
C8 O1 3.301(2) no 2_566
C8 N3 3.394(3) no 1_545
C9 N1 3.583(3) no .
C9 N2 3.543(3) no 2_677
C9 N3 3.481(3) no 2_577
N4 H5A 2.68(3) no .
N4 H5B 3.32(3) no .
N4 H5C 2.62(3) no .
N4 H6A 2.68(3) no .
N4 H6B 2.76(3) no .
N4 H6C 3.37(2) no .
N4 H8A 3.30(2) no .
N4 H8B 2.75(2) no .
N4 H8C 2.736(19) no .
N4 H9A 2.66(3) no .
N4 H9B 3.33(3) no .
N4 H9C 2.65(3) no .
C4 H7 2.77(2) no .
C4 H8B 3.42(2) no .
C4 H8C 2.75(2) no .
C5 H6A 2.74(3) no .
C5 H6B 3.38(3) no .
C5 H6C 2.72(2) no .
C5 H4A 2.65(3) no .
C5 H4B 2.54(3) no .
C6 H5A 2.69(2) no .
C6 H5B 2.73(3) no .
C6 H5C 3.38(3) no .
C6 H7 2.72(2) no .
C6 H8C 3.27(2) no .
C6 H4A 2.66(2) no .
C6 H4B 3.29(3) no .
C7 H4 2.71(2) no .
C7 H6A 3.35(2) no .
C7 H6B 2.83(3) no .
C8 H4 2.66(2) no .
C8 H6B 3.33(3) no .
C8 H9A 2.68(2) no .
C8 H9B 2.74(2) no .
C8 H9C 3.37(2) no .
C8 H4A 3.340(19) no .
C8 H4B 2.68(2) no .
C9 H8A 2.714(18) no .
C9 H8B 2.72(2) no .
C9 H8C 3.42(2) no .
C9 H4A 2.56(3) no .
C9 H4B 2.59(3) no .
H4 H5A 2.91(3) no .
H4 H5B 2.45(3) no .
H4 H5C 2.42(3) no .
H4 H6A 2.89(3) no .
H4 H6B 2.39(3) no .
H4 H6C 2.48(3) no .
H4 H7 3.02(3) no .
H4 H8A 3.51(3) no .
H4 H8B 2.94(3) no .
H4 H8C 2.12(3) no .
H4 H4A 2.84(3) no .
H4 H4B 2.31(3) no .
H5A H6A 2.54(4) no .
H5A H6C 2.95(3) no .
H5A H4A 2.48(4) no .
H5A H4B 2.88(4) no .
H5B H6A 3.04(4) no .
H5B H6C 2.55(3) no .
H5B H4A 3.56(4) no .
H5B H4B 3.47(4) no .
H5C H4A 2.92(4) no .
H5C H4B 2.35(4) no .
H6A H7 2.91(3) no .
H6A H4A 2.48(3) no .
H6A H4B 3.52(4) no .
H6B H7 2.27(3) no .
H6B H8C 2.86(4) no .
H6B H4A 3.04(3) no .
H6C H4A 3.57(3) no .
H7 H8A 2.38(3) no .
H7 H8B 2.92(3) no .
H7 H8C 2.43(3) no .
H7 H9A 2.82(3) no .
H7 H9B 2.40(3) no .
H7 H9C 2.36(3) no .
H7 H4A 2.31(3) no .
H7 H4B 2.80(3) no .
H8A H9A 2.95(3) no .
H8A H9B 2.59(3) no .
H8A H4B 3.53(3) no .
H8B H9A 2.52(3) no .
H8B H9B 3.02(3) no .
H8B H4B 2.58(3) no .
H8C H4B 3.04(3) no .
H9A H4A 2.88(4) no .
H9A H4B 2.46(4) no .
H9B H4A 3.49(4) no .
H9B H4B 3.53(4) no .
H9C H4A 2.37(4) no .
H9C H4B 2.88(4) no .
O1 H4 2.69(2) no .
O1 H5C 3.17(2) no .
O1 H5C 3.16(3) no 2_676
O1 H6B 3.58(3) no 2_666
O1 H6C 2.58(2) no 2_666
O1 H8A 2.625(19) no 2_566
O1 H8B 2.94(3) no .
O1 H8C 3.24(3) no .
O1 H8C 3.12(2) no 2_566
O1 H9B 3.24(2) no 1_554
O1 H9C 3.20(3) no 1_554
O1 H4B 3.21(2) no .
N1 H5C 3.10(3) no .
N1 H6B 3.49(2) no 1_565
N1 H8B 3.01(2) no .
N1 H9A 2.92(3) no .
N1 H9C 2.81(2) no 2_677
N1 H4A 3.38(2) no .
N1 H4A 2.724(19) no 2_677
N1 H4B 1.97(3) no .
N2 H5A 3.18(3) no 2_677
N2 H6A 2.99(2) no 2_677
N2 H6B 3.04(3) no 1_565
N2 H7 3.32(2) no 1_565
N2 H7 3.453(16) no 2_677
N2 H9A 2.98(3) no .
N2 H9C 2.82(3) no 2_677
N2 H4A 1.85(2) no 2_677
N2 H4B 2.90(3) no .
N2 H4B 3.30(2) no 2_677
N3 H5A 3.57(3) no 2_677
N3 H6A 2.984(19) no 2_677
N3 H6B 3.19(2) no 1_565
N3 H7 2.855(18) no 1_565
N3 H8A 3.01(3) no 1_565
N3 H8C 3.21(3) no 1_565
N3 H9A 3.38(3) no 2_577
N3 H9B 2.75(3) no 2_577
N3 H4A 2.92(2) no 2_677
C1 H5B 3.49(3) no 1_455
C1 H5B 3.38(2) no 2_676
C1 H5C 3.01(3) no 2_676
C1 H8A 3.21(2) no 2_566
C1 H8B 2.94(3) no .
C1 H8C 3.24(2) no 2_566
C1 H4B 3.46(2) no .
C2 H5B 3.45(2) no 1_455
C2 H5B 3.29(3) no 2_676
C2 H5C 3.40(3) no 2_676
C2 H8B 2.96(3) no .
C2 H4B 2.95(3) no .
C3 H5A 3.38(3) no 2_676
C3 H5B 3.33(3) no 1_455
C3 H5B 3.43(2) no 2_676
C3 H5C 3.43(2) no 2_676
C3 H8A 3.36(2) no 2_566
C3 H8C 3.27(2) no 2_566
C3 H9B 3.51(3) no 1_554
C4 H4 3.476(19) no 2_666
C4 H6C 3.248(19) no 2_666
C5 H8B 3.36(3) no 1_655
C5 H9C 3.57(2) no 2_677
C6 H4 3.193(19) no 2_666
C6 H5B 3.584(19) no 2_666
C6 H7 3.06(2) no 2_667
C6 H8A 3.23(3) no 1_655
C6 H9B 3.47(3) no 2_667
C6 H9C 3.26(3) no 2_667
C7 H6A 3.22(3) no 2_667
C7 H6B 3.53(2) no 2_667
C8 H5B 3.54(3) no 1_455
C8 H6C 3.30(2) no 1_455
C8 H8B 3.55(2) no 2_566
C8 H8C 3.16(2) no 2_566
C9 H5A 3.55(2) no 2_677
C9 H5C 3.53(2) no 2_677
C9 H6A 3.25(2) no 2_667
C9 H6B 3.40(3) no 2_667
H4 O1 2.69(2) no .
H4 C4 3.476(19) no 2_666
H4 C6 3.193(19) no 2_666
H4 H4 3.16(3) no 2_666
H4 H5B 3.11(3) no 2_666
H4 H6B 3.46(3) no 2_666
H4 H6C 2.39(3) no 2_666
H5A N2 3.18(3) no 2_677
H5A N3 3.57(3) no 2_677
H5A C3 3.38(3) no 2_676
H5A C9 3.55(2) no 2_677
H5A H8A 3.58(4) no 1_655
H5A H8B 3.02(4) no 1_655
H5A H9A 3.14(3) no 1_655
H5A H9A 2.98(3) no 2_677
H5A H9C 3.37(4) no 2_677
H5B C1 3.49(3) no 1_655
H5B C1 3.38(2) no 2_676
H5B C2 3.45(2) no 1_655
H5B C2 3.29(3) no 2_676
H5B C3 3.33(3) no 1_655
H5B C3 3.43(2) no 2_676
H5B C6 3.584(19) no 2_666
H5B C8 3.54(3) no 1_655
H5B H4 3.11(3) no 2_666
H5B H6B 3.21(3) no 2_666
H5B H6C 3.33(3) no 2_666
H5B H8A 3.42(4) no 1_655
H5B H8B 2.73(3) no 1_655
H5B H8C 3.01(4) no 2_666
H5C O1 3.17(2) no .
H5C O1 3.16(3) no 2_676
H5C N1 3.10(3) no .
H5C C1 3.01(3) no 2_676
H5C C2 3.40(3) no 2_676
H5C C3 3.43(2) no 2_676
H5C C9 3.53(2) no 2_677
H5C H9A 3.36(3) no 2_677
H5C H9C 2.92(3) no 2_677
H6A N2 2.99(2) no 2_677
H6A N3 2.984(19) no 2_677
H6A C7 3.22(3) no 2_667
H6A C9 3.25(2) no 2_667
H6A H7 2.43(3) no 2_667
H6A H8A 2.94(4) no 1_655
H6A H8B 3.57(4) no 1_655
H6A H9B 3.15(3) no 1_655
H6A H9B 2.96(4) no 2_667
H6A H9C 3.10(4) no 2_667
H6B O1 3.58(3) no 2_666
H6B N1 3.49(2) no 1_545
H6B N2 3.04(3) no 1_545
H6B N3 3.19(2) no 1_545
H6B C7 3.53(2) no 2_667
H6B C9 3.40(3) no 2_667
H6B H4 3.46(3) no 2_666
H6B H5B 3.21(3) no 2_666
H6B H7 2.85(3) no 2_667
H6B H9B 3.46(4) no 2_667
H6B H9C 2.82(4) no 2_667
H6B H4A 3.55(4) no 2_667
H6C O1 2.58(2) no 2_666
H6C C4 3.248(19) no 2_666
H6C C8 3.30(2) no 1_655
H6C H4 2.39(3) no 2_666
H6C H5B 3.33(3) no 2_666
H6C H8A 2.56(3) no 1_655
H6C H8B 3.18(3) no 1_655
H6C H8C 3.36(4) no 2_666
H6C H9B 3.34(3) no 2_667
H6C H9C 3.24(4) no 2_667
H7 N2 3.32(2) no 1_545
H7 N2 3.453(16) no 2_677
H7 N3 2.855(18) no 1_545
H7 C6 3.06(2) no 2_667
H7 H6A 2.43(3) no 2_667
H7 H6B 2.85(3) no 2_667
H7 H7 3.21(3) no 2_667
H8A O1 2.625(19) no 2_566
H8A N3 3.01(3) no 1_545
H8A C1 3.21(2) no 2_566
H8A C3 3.36(2) no 2_566
H8A C6 3.23(3) no 1_455
H8A H5A 3.58(4) no 1_455
H8A H5B 3.42(4) no 1_455
H8A H6A 2.94(4) no 1_455
H8A H6C 2.56(3) no 1_455
H8A H8C 3.22(3) no 2_566
H8A H9B 2.99(4) no 2_567
H8B O1 2.94(3) no .
H8B N1 3.01(2) no .
H8B C1 2.94(3) no .
H8B C2 2.96(3) no .
H8B C5 3.36(3) no 1_455
H8B C8 3.55(2) no 2_566
H8B H5A 3.02(4) no 1_455
H8B H5B 2.73(3) no 1_455
H8B H6A 3.57(4) no 1_455
H8B H6C 3.18(3) no 1_455
H8B H8C 2.80(3) no 2_566
H8C O1 3.24(3) no .
H8C O1 3.12(2) no 2_566
H8C N3 3.21(3) no 1_545
H8C C1 3.24(2) no 2_566
H8C C3 3.27(2) no 2_566
H8C C8 3.16(2) no 2_566
H8C H5B 3.01(4) no 2_666
H8C H6C 3.36(4) no 2_666
H8C H8A 3.22(3) no 2_566
H8C H8B 2.80(3) no 2_566
H8C H8C 2.85(3) no 2_566
H9A N1 2.92(3) no .
H9A N2 2.98(3) no .
H9A N3 3.38(3) no 2_577
H9A H5A 3.14(3) no 1_455
H9A H5A 2.98(3) no 2_677
H9A H5C 3.36(3) no 2_677
H9A H4A 3.21(3) no 2_677
H9A H4B 3.54(3) no 2_677
H9B O1 3.24(2) no 1_556
H9B N3 2.75(3) no 2_577
H9B C3 3.51(3) no 1_556
H9B C6 3.47(3) no 2_667
H9B H6A 3.15(3) no 1_455
H9B H6A 2.96(4) no 2_667
H9B H6B 3.46(4) no 2_667
H9B H6C 3.34(3) no 2_667
H9B H8A 2.99(4) no 2_567
H9B H9B 3.18(3) no 2_567
H9C O1 3.20(3) no 1_556
H9C N1 2.81(2) no 2_677
H9C N2 2.82(3) no 2_677
H9C C5 3.57(2) no 2_677
H9C C6 3.26(3) no 2_667
H9C H5A 3.37(4) no 2_677
H9C H5C 2.92(3) no 2_677
H9C H6A 3.10(4) no 2_667
H9C H6B 2.82(4) no 2_667
H9C H6C 3.24(4) no 2_667
H9C H4A 3.55(3) no 2_677
H9C H4B 3.14(3) no 2_677
H4A N1 3.38(2) no .
H4A N1 2.724(19) no 2_677
H4A N2 1.85(2) no 2_677
H4A N3 2.92(2) no 2_677
H4A H6B 3.55(4) no 2_667
H4A H9A 3.21(3) no 2_677
H4A H9C 3.55(3) no 2_677
H4A H4B 3.28(3) no 2_677
H4B O1 3.21(2) no .
H4B N1 1.97(3) no .
H4B N2 2.90(3) no .
H4B N2 3.30(2) no 2_677
H4B C1 3.46(2) no .
H4B C2 2.95(3) no .
H4B H9A 3.54(3) no 2_677
H4B H9C 3.14(3) no 2_677
H4B H4A 3.28(3) no 2_677
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4A N2 2_677 2.8514(19) 1.010(19) 1.85(2) 174(2) no
N4 H4B N1 . 2.901(3) 0.94(3) 1.97(3) 171(2) no
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_publ_flag
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 N1 C2 C1 179.69(15) no . .
N2 N1 C2 C3 -0.36(19) no . 2_576
C2 N1 N2 N3 0.3(2) no . .
N1 N2 N3 C3 -0.09(19) no . 2_576
N2 N3 C3 C1 178.35(16) no 2_576 2_576
N2 N3 C3 C2 -0.14(19) no 2_576 .
C4 N4 C7 C8 -59.5(2) no . .
C4 N4 C7 C9 177.15(14) no . .
C7 N4 C4 C5 175.38(14) no . .
C7 N4 C4 C6 -61.78(18) no . .
O1 C1 C2 N1 -2.0(3) no . .
O1 C1 C2 C3 178.09(17) no . 2_576
O1 C1 C3 N3 0.2(3) no . 2_576
O1 C1 C3 C2 -178.11(17) no . 2_576
C2 C1 C3 N3 179.75(17) no . 2_576
C2 C1 C3 C2 1.5(3) no . 2_576
C3 C1 C2 N1 178.42(16) no . .
C3 C1 C2 C3 -1.5(3) no . 2_576
N1 C2 C3 N3 0.3(2) no 2_576 .
N1 C2 C3 C1 -178.24(16) no 2_576 2_576
C1 C2 C3 N3 -179.73(16) no 2_576 .
C1 C2 C3 C1 1.7(3) no 2_576 2_576
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203062
