#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/33/2203314.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2203314
loop_
_publ_author_name
'Miao Du'
'Xiao-Jun Zhao'
_publ_section_title
;
 2-(2-Pyridylamino)pyridinium nitrate monohydrate: two-dimensional
 supramolecular aggregation through hydrogen-bonding and π--π
 stacking interactions
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o439
_journal_page_last               o441
_journal_paper_doi               10.1107/S1600536804004015
_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'
_space_group_IT_number           2
_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       ω
_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 0
_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      ?
_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_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/[σ²(Fo²)+(0.0606P)²+0.6420P] where P = (Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            lh6172.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        ' C10 H12 N4 O4 '
_cod_database_code               2203314
_cod_database_fobs_code          2203314
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_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_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
_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_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
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)
