#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203314.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_2203314
loop_
_publ_author_name
'Miao Du'
'Xiao-Jun Zhao'
_publ_section_title
; (2-Pyridinio-2'-pyridyl)amine nitrate hydrate:
two-dimensional (2-D) supramolecular
aggregation through hydrogen-bonding and
\p-\p stacking interactions
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o439
_journal_page_last             o441
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        ' C10 H12 N4 O4 '
_chemical_formula_moiety       ' C10 H10 N3, N O3, H2 O'
_chemical_formula_sum          ' C10 H12 N4 O4 '
_chemical_formula_weight       252.24
_chemical_name_systematic      ' (2-Pyridinio-2'-pyridyl)amine nitrate hydrate'
_symmetry_cell_setting         Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_cell_angle_alpha              95.982(6)
_cell_angle_beta               102.332(6)
_cell_angle_gamma              110.480(5)
_cell_formula_units_Z          4
_cell_length_a                 7.795(2)
_cell_length_b                 9.734(3)
_cell_length_c                 17.164(5)
_cell_measurement_reflns_used  845
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    25.00
_cell_measurement_theta_min    2.28
_cell_volume                   1168.9(6)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_data_reduction      'SAINT (Bruker, 1998)'
_computing_molecular_graphics  'DIAMOND (Brandenburg & Berndt, 1999)'
_computing_publication_material SHELXL97
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device     'BRUKER SMART 1000 diffractometer'
_diffrn_measurement_method     \w
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0182
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_l_max     19
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_number          4852
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       25.00
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count none
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.113
_exptl_absorpt_correction_T_max 0.9777
_exptl_absorpt_correction_T_min 0.9668
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'[SAINT (Bruker 1998) and SADABS (Sheldrick, 1998)]'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.433
_exptl_crystal_density_meas    'not measured'
_exptl_crystal_description     block
_exptl_crystal_F_000           528
_exptl_crystal_size_max        0.30
_exptl_crystal_size_mid        0.20
_exptl_crystal_size_min        0.20
_refine_diff_density_max       0.732
_refine_diff_density_min       -0.450
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.102
_refine_ls_hydrogen_treatment  constr
_refine_ls_number_parameters   328
_refine_ls_number_reflns       4088
_refine_ls_restrained_S_all    1.109
_refine_ls_R_factor_all        0.1220
_refine_ls_R_factor_gt         0.0677
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.6420P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1573
_refine_ls_wR_factor_ref       0.1822
_reflns_number_gt              2266
_reflns_number_total           4088
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.4234(5) 0.7232(4) 0.1797(2) 0.1012(12) Uani d . 1 . . O
O2 0.5142(4) 0.9570(3) 0.1957(2) 0.0934(11) Uani d . 1 . . O
O3 0.6887(5) 0.8491(5) 0.1603(2) 0.1119(13) Uani d . 1 . . O
O4 0.3006(7) 0.3156(5) 0.3487(3) 0.166(2) Uani d . 1 . . O
O5 0.3951(4) 0.1399(4) 0.3268(2) 0.0846(9) Uani d . 1 . . O
O6 0.1037(5) 0.1059(4) 0.2904(3) 0.1204(15) Uani d . 1 . . O
N1 0.8552(4) 0.6273(3) 1.05874(17) 0.0490(8) Uani d D 1 . . N
H1 0.9256 0.7017 1.0979 0.059 Uiso calc RD 1 . . H
N2 0.6526(4) 0.5560(3) 0.92712(17) 0.0497(8) Uani d D 1 . . N
H2 0.6351 0.4644 0.9294 0.060 Uiso calc RD 1 . . H
N3 0.7338(4) 0.3693(3) 1.01641(18) 0.0544(8) Uani d . 1 . . N
N4 0.7763(4) 0.4024(3) 0.43517(16) 0.0455(7) Uani d D 1 . . N
H4 0.7938 0.3435 0.3995 0.055 Uiso calc RD 1 . . H
N5 0.7179(4) 0.4306(4) 0.56278(18) 0.0577(8) Uani d D 1 . . N
H5 0.7310 0.5215 0.5605 0.069 Uiso calc RD 1 . . H
N6 0.7849(4) 0.6410(3) 0.4740(2) 0.0609(9) Uani d . 1 . . N
N7 0.5448(5) 0.8439(4) 0.17742(18) 0.0565(8) Uani d . 1 . . N
N8 0.2665(6) 0.1826(4) 0.3265(2) 0.0663(9) Uani d . 1 . . N
C1 0.7652(5) 0.6628(4) 0.9918(2) 0.0428(8) Uani d . 1 . . C
C2 0.7893(5) 0.8104(4) 0.9876(2) 0.0512(9) Uani d . 1 . . C
H2A 0.8662 0.8868 1.0318 0.061 Uiso calc R 1 . . H
C3 0.7012(6) 0.8424(5) 0.9193(3) 0.0635(11) Uani d . 1 . . C
H3A 0.7172 0.9410 0.9169 0.076 Uiso calc R 1 . . H
C4 0.5864(6) 0.7290(5) 0.8525(3) 0.0658(11) Uani d . 1 . . C
H4A 0.5262 0.7508 0.8053 0.079 Uiso calc R 1 . . H
C5 0.5646(6) 0.5876(5) 0.8578(2) 0.0610(11) Uani d . 1 . . C
H5A 0.4889 0.5105 0.8137 0.073 Uiso calc R 1 . . H
C6 0.8503(5) 0.4890(4) 1.0734(2) 0.0438(8) Uani d . 1 . . C
C7 0.9653(5) 0.4803(5) 1.1449(2) 0.0588(10) Uani d . 1 . . C
H7A 1.0476 0.5660 1.1827 0.071 Uiso calc R 1 . . H
C8 0.9537(6) 0.3406(5) 1.1580(3) 0.0653(11) Uani d . 1 . . C
H8A 1.0286 0.3308 1.2054 0.078 Uiso calc R 1 . . H
C9 0.8313(7) 0.2156(5) 1.1010(3) 0.0695(12) Uani d . 1 . . C
H9A 0.8204 0.1204 1.1093 0.083 Uiso calc R 1 . . H
C10 0.7263(6) 0.2354(4) 1.0316(3) 0.0647(11) Uani d . 1 . . C
H10A 0.6447 0.1510 0.9927 0.078 Uiso calc R 1 . . H
C11 0.7365(4) 0.3464(4) 0.5016(2) 0.0439(9) Uani d . 1 . . C
C12 0.7182(5) 0.1998(4) 0.5069(2) 0.0578(10) Uani d . 1 . . C
H12A 0.7308 0.1399 0.4644 0.069 Uiso calc R 1 . . H
C13 0.6827(6) 0.1452(5) 0.5727(3) 0.0723(13) Uani d . 1 . . C
H13A 0.6725 0.0480 0.5760 0.087 Uiso calc R 1 . . H
C14 0.6615(6) 0.2315(6) 0.6348(3) 0.0772(14) Uani d . 1 . . C
H14A 0.6360 0.1927 0.6802 0.093 Uiso calc R 1 . . H
C15 0.6771(6) 0.3730(6) 0.6308(2) 0.0752(14) Uani d . 1 . . C
H15A 0.6610 0.4314 0.6729 0.090 Uiso calc R 1 . . H
C16 0.7924(5) 0.5405(4) 0.4173(2) 0.0463(9) Uani d . 1 . . C
C17 0.8179(5) 0.5694(5) 0.3418(2) 0.0619(11) Uani d . 1 . . C
H17A 0.8222 0.4971 0.3032 0.074 Uiso calc R 1 . . H
C18 0.8365(6) 0.7099(6) 0.3267(3) 0.0807(15) Uani d . 1 . . C
H18A 0.8536 0.7342 0.2772 0.097 Uiso calc R 1 . . H
C19 0.8296(6) 0.8139(6) 0.3857(4) 0.0909(17) Uani d . 1 . . C
H19A 0.8426 0.9091 0.3766 0.109 Uiso calc R 1 . . H
C20 0.8036(6) 0.7754(5) 0.4567(4) 0.0812(14) Uani d . 1 . . C
H20A 0.7983 0.8462 0.4959 0.097 Uiso calc R 1 . . H
O1W 0.1092(4) 0.8689(3) 0.17904(16) 0.0676(8) Uani d D 1 . . O
H1WA 0.0799 0.9230 0.2159 0.101 Uiso d RD 1 . . H
H1WB 0.2305 0.8834 0.1833 0.101 Uiso d RD 1 . . H
O2W 0.8092(4) 0.1897(3) 0.32182(17) 0.0761(9) Uani d D 1 . . O
H2WA 0.9166 0.1859 0.3126 0.114 Uiso d RD 1 . . H
H2WB 0.6988 0.1329 0.2849 0.114 Uiso d RD 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.107(3) 0.063(2) 0.111(3) 0.006(2) 0.039(2) -0.0044(18)
O2 0.079(2) 0.057(2) 0.135(3) 0.0331(17) 0.011(2) -0.0049(18)
O3 0.100(3) 0.164(4) 0.131(3) 0.085(3) 0.072(2) 0.067(3)
O4 0.176(5) 0.113(4) 0.195(5) 0.062(3) 0.049(4) -0.047(3)
O5 0.072(2) 0.087(2) 0.099(2) 0.0426(19) 0.0114(18) 0.0162(18)
O6 0.060(2) 0.100(3) 0.180(4) 0.027(2) 0.021(2) -0.025(3)
N1 0.0561(19) 0.0378(17) 0.0493(18) 0.0166(14) 0.0102(15) 0.0059(13)
N2 0.0535(19) 0.0460(18) 0.0503(18) 0.0209(15) 0.0129(15) 0.0087(15)
N3 0.065(2) 0.0389(18) 0.061(2) 0.0212(15) 0.0193(17) 0.0092(15)
N4 0.0487(18) 0.0434(17) 0.0411(16) 0.0152(14) 0.0104(14) 0.0063(13)
N5 0.0495(19) 0.065(2) 0.055(2) 0.0215(16) 0.0112(16) 0.0057(17)
N6 0.054(2) 0.0414(19) 0.087(2) 0.0207(15) 0.0142(18) 0.0104(17)
N7 0.062(2) 0.059(2) 0.0506(19) 0.0256(19) 0.0146(17) 0.0092(16)
N8 0.075(3) 0.052(2) 0.073(2) 0.028(2) 0.023(2) -0.0054(18)
C1 0.043(2) 0.045(2) 0.043(2) 0.0168(16) 0.0153(17) 0.0095(17)
C2 0.057(2) 0.042(2) 0.058(2) 0.0181(18) 0.0195(19) 0.0135(18)
C3 0.076(3) 0.056(3) 0.078(3) 0.035(2) 0.033(2) 0.031(2)
C4 0.079(3) 0.079(3) 0.061(3) 0.046(3) 0.026(2) 0.034(2)
C5 0.060(3) 0.077(3) 0.045(2) 0.030(2) 0.0075(19) 0.007(2)
C6 0.044(2) 0.043(2) 0.052(2) 0.0190(17) 0.0203(18) 0.0160(17)
C7 0.054(2) 0.063(3) 0.063(3) 0.023(2) 0.016(2) 0.021(2)
C8 0.070(3) 0.078(3) 0.070(3) 0.041(3) 0.030(2) 0.041(3)
C9 0.087(3) 0.057(3) 0.096(3) 0.043(3) 0.050(3) 0.038(3)
C10 0.086(3) 0.042(2) 0.076(3) 0.028(2) 0.033(3) 0.015(2)
C11 0.0327(19) 0.051(2) 0.040(2) 0.0119(16) 0.0020(16) 0.0050(17)
C12 0.052(2) 0.051(2) 0.062(3) 0.0135(18) 0.009(2) 0.0157(19)
C13 0.061(3) 0.073(3) 0.078(3) 0.018(2) 0.014(2) 0.029(3)
C14 0.058(3) 0.097(4) 0.075(3) 0.022(3) 0.014(2) 0.044(3)
C15 0.050(3) 0.125(4) 0.047(3) 0.034(3) 0.013(2) 0.002(3)
C16 0.035(2) 0.046(2) 0.054(2) 0.0144(16) 0.0045(17) 0.0132(18)
C17 0.051(2) 0.063(3) 0.064(3) 0.013(2) 0.007(2) 0.024(2)
C18 0.050(3) 0.092(4) 0.092(4) 0.014(3) 0.007(2) 0.051(3)
C19 0.059(3) 0.056(3) 0.155(5) 0.020(2) 0.014(3) 0.046(4)
C20 0.067(3) 0.056(3) 0.121(4) 0.028(2) 0.020(3) 0.015(3)
O1W 0.0533(16) 0.0633(18) 0.0747(18) 0.0179(13) 0.0089(14) -0.0028(14)
O2W 0.0599(18) 0.082(2) 0.0789(19) 0.0285(15) 0.0166(15) -0.0142(16)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C6 . . 129.6(3) yes
C1 N1 H1 . . 115.2 ?
C6 N1 H1 . . 115.2 ?
C1 N2 C5 . . 122.1(3) yes
C1 N2 H2 . . 119.0 ?
C5 N2 H2 . . 119.0 ?
C6 N3 C10 . . 117.1(3) yes
C11 N4 C16 . . 128.9(3) yes
C11 N4 H4 . . 115.5 ?
C16 N4 H4 . . 115.5 ?
C11 N5 C15 . . 120.6(4) yes
C11 N5 H5 . . 119.7 ?
C15 N5 H5 . . 119.7 ?
C16 N6 C20 . . 117.5(4) yes
O3 N7 O2 . . 122.3(4) ?
O3 N7 O1 . . 120.7(4) ?
O2 N7 O1 . . 117.0(4) ?
O6 N8 O5 . . 122.3(4) ?
O6 N8 O4 . . 115.8(4) ?
O5 N8 O4 . . 120.3(4) ?
N2 C1 N1 . . 120.3(3) ?
N2 C1 C2 . . 118.2(3) ?
N1 C1 C2 . . 121.5(3) ?
C3 C2 C1 . . 120.0(4) ?
C3 C2 H2A . . 120.0 ?
C1 C2 H2A . . 120.0 ?
C2 C3 C4 . . 120.5(4) ?
C2 C3 H3A . . 119.7 ?
C4 C3 H3A . . 119.7 ?
C5 C4 C3 . . 118.5(4) ?
C5 C4 H4A . . 120.7 ?
C3 C4 H4A . . 120.7 ?
C4 C5 N2 . . 120.6(4) ?
C4 C5 H5A . . 119.7 ?
N2 C5 H5A . . 119.7 ?
N3 C6 N1 . . 117.3(3) ?
N3 C6 C7 . . 123.1(3) ?
N1 C6 C7 . . 119.6(3) ?
C8 C7 C6 . . 117.8(4) ?
C8 C7 H7A . . 121.1 ?
C6 C7 H7A . . 121.1 ?
C9 C8 C7 . . 120.0(4) ?
C9 C8 H8A . . 120.0 ?
C7 C8 H8A . . 120.0 ?
C10 C9 C8 . . 118.0(4) ?
C10 C9 H9A . . 121.0 ?
C8 C9 H9A . . 121.0 ?
N3 C10 C9 . . 123.9(4) ?
N3 C10 H10A . . 118.1 ?
C9 C10 H10A . . 118.1 ?
N5 C11 N4 . . 120.7(3) ?
N5 C11 C12 . . 119.1(3) ?
N4 C11 C12 . . 120.2(3) ?
C13 C12 C11 . . 120.5(4) ?
C13 C12 H12A . . 119.7 ?
C11 C12 H12A . . 119.7 ?
C12 C13 C14 . . 120.2(5) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C15 C14 C13 . . 120.4(4) ?
C15 C14 H14A . . 119.8 ?
C13 C14 H14A . . 119.8 ?
C14 C15 N5 . . 119.3(4) ?
C14 C15 H15A . . 120.3 ?
N5 C15 H15A . . 120.3 ?
N6 C16 N4 . . 117.8(3) ?
N6 C16 C17 . . 123.1(4) ?
N4 C16 C17 . . 119.0(3) ?
C18 C17 C16 . . 117.3(4) ?
C18 C17 H17A . . 121.4 ?
C16 C17 H17A . . 121.4 ?
C19 C18 C17 . . 119.5(5) ?
C19 C18 H18A . . 120.3 ?
C17 C18 H18A . . 120.3 ?
C20 C19 C18 . . 119.0(5) ?
C20 C19 H19A . . 120.5 ?
C18 C19 H19A . . 120.5 ?
N6 C20 C19 . . 123.7(5) ?
N6 C20 H20A . . 118.2 ?
C19 C20 H20A . . 118.2 ?
H1WA O1W H1WB . . 119.6 ?
H2WA O2W H2WB . . 117.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N7 . 1.235(4) ?
O2 N7 . 1.229(4) ?
O3 N7 . 1.205(4) ?
O4 N8 . 1.227(5) ?
O5 N8 . 1.212(4) ?
O6 N8 . 1.207(4) ?
N1 C1 . 1.357(4) yes
N1 C6 . 1.384(4) yes
N1 H1 . 0.8600 ?
N2 C1 . 1.337(4) yes
N2 C5 . 1.363(4) yes
N2 H2 . 0.8600 ?
N3 C6 . 1.335(4) yes
N3 C10 . 1.339(5) yes
N4 C11 . 1.362(4) yes
N4 C16 . 1.380(4) yes
N4 H4 . 0.8600 ?
N5 C11 . 1.328(4) yes
N5 C15 . 1.396(5) yes
N5 H5 . 0.8600 ?
N6 C16 . 1.331(5) yes
N6 C20 . 1.337(5) yes
C1 C2 . 1.393(5) ?
C2 C3 . 1.351(5) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.393(6) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.342(5) ?
C4 H4A . 0.9300 ?
C5 H5A . 0.9300 ?
C6 C7 . 1.386(5) ?
C7 C8 . 1.376(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.374(6) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.366(6) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.398(5) ?
C12 C13 . 1.337(5) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.363(6) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.350(6) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
C16 C17 . 1.394(5) ?
C17 C18 . 1.382(6) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.379(7) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.347(7) ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9300 ?
O1W H1WA . 0.8977 ?
O1W H1WB . 0.8916 ?
O2W H2WA . 0.8964 ?
O2W H2WB . 0.8992 ?
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_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1w 1_656 0.860 1.920 2.775(5) 172.7 yes
N2 H2 N3 1_555 0.860 1.994 2.650(5) 132.3 yes
N2 H2 O1 2_666 0.860 2.321 2.910(4) 125.9 yes
N4 H4 O2w 1_555 0.860 1.952 2.808(4) 172.9 yes
N5 H5 N6 1_555 0.860 2.004 2.651(5) 131.3 yes
N5 H5 O4 2_666 0.860 2.221 2.827(5) 127.4 yes
O1w H1wa O6 1_565 0.898 2.009 2.857(4) 157.2 yes
O1w H1wb O2 1_555 0.892 2.027 2.908(5) 169.4 yes
O2w H2wa O6 1_655 0.896 1.962 2.823(4) 160.6 yes
O2w H2wb O2 1_545 0.899 2.034 2.883(4) 157.0 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N2 C1 N1 . . . . -177.8(3) ?
C5 N2 C1 C2 . . . . 1.1(5) ?
C6 N1 C1 N2 . . . . -0.3(5) ?
C6 N1 C1 C2 . . . . -179.2(3) ?
N2 C1 C2 C3 . . . . -0.5(5) ?
N1 C1 C2 C3 . . . . 178.5(3) ?
C1 C2 C3 C4 . . . . -0.3(6) ?
C2 C3 C4 C5 . . . . 0.4(6) ?
C3 C4 C5 N2 . . . . 0.2(6) ?
C1 N2 C5 C4 . . . . -1.0(5) ?
C10 N3 C6 N1 . . . . -178.5(3) ?
C10 N3 C6 C7 . . . . 2.0(5) ?
C1 N1 C6 N3 . . . . -4.0(5) ?
C1 N1 C6 C7 . . . . 175.5(3) ?
N3 C6 C7 C8 . . . . -1.8(5) ?
N1 C6 C7 C8 . . . . 178.8(3) ?
C6 C7 C8 C9 . . . . 0.2(6) ?
C7 C8 C9 C10 . . . . 1.0(6) ?
C6 N3 C10 C9 . . . . -0.7(6) ?
C8 C9 C10 N3 . . . . -0.8(6) ?
C15 N5 C11 N4 . . . . -180.0(3) ?
C15 N5 C11 C12 . . . . -1.2(5) ?
C16 N4 C11 N5 . . . . -4.0(5) ?
C16 N4 C11 C12 . . . . 177.3(3) ?
N5 C11 C12 C13 . . . . -0.1(5) ?
N4 C11 C12 C13 . . . . 178.7(3) ?
C11 C12 C13 C14 . . . . 0.9(6) ?
C12 C13 C14 C15 . . . . -0.4(7) ?
C13 C14 C15 N5 . . . . -0.8(6) ?
C11 N5 C15 C14 . . . . 1.6(5) ?
C20 N6 C16 N4 . . . . 179.0(3) ?
C20 N6 C16 C17 . . . . -0.2(5) ?
C11 N4 C16 N6 . . . . 6.4(5) ?
C11 N4 C16 C17 . . . . -174.4(3) ?
N6 C16 C17 C18 . . . . 0.2(5) ?
N4 C16 C17 C18 . . . . -179.0(3) ?
C16 C17 C18 C19 . . . . 0.1(6) ?
C17 C18 C19 C20 . . . . -0.4(7) ?
C16 N6 C20 C19 . . . . -0.1(6) ?
C18 C19 C20 N6 . . . . 0.4(7) ?