#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/87/2008794.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_2008794
loop_
_publ_author_name
'Velikova, Velichka'
Bakardjeva,Snejana
Angelova,Olyana
_publ_section_title
;
 N-(2-Pyridinium)urea nitrate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1328
_journal_page_last               1330
_journal_paper_doi               10.1107/S0108270199000876
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C6 H8 N3 O +, N O3 -'
_chemical_formula_sum            'C6 H8 N4 O4'
_chemical_formula_weight         200.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.070(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0861(10)
_cell_length_b                   12.198(2)
_cell_length_c                   13.760(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.45
_cell_measurement_theta_min      20.55
_cell_volume                     848.9(3)
_computing_cell_refinement       CAD4
_computing_data_collection       'CAD4  (Enraf-Nonius, 1988)'
_computing_data_reduction        'DATARED (Vassilev, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292
_diffrn_measured_fraction_theta_full 0.871
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  'graphite (perpendicular mode)'
_diffrn_radiation_source         '2kW fine focus Philips tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3950
_diffrn_reflns_reduction_process
;
  F^2^ = (Int-2*(BgL+BgR))*ATN/(NPI*LP)
  \s(F^2^) = (Int+4*(BgL+BgR))^1/2^*ATN/(NPI*LP)
  where Int = Total count for the reflection,
        BgL = Left background count,
        BgR = Right background count,
        ATN = Attenuator factor (1.0 if unused),
        NPI = Ratio of the fastest possible scan rate to
  scan rate for the measurement,
        LP  = Lorentz-polarization correction.
  LP = 0.5*(cos^2^2\q~m~+cos^2^2\q~c~)/(1+cos^2^2\q~m~)+
       0.5*(1+cos2\q~m~+cos^2^2\q~c~)/[(1+cos2\q~m~)*sin(2\q~c~)]
  where \q~m~ = theta angle for the monochromator crystal (12.2 deg for Mo),
        \q~c~ = theta angle for sample crystal.
;
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0690P)²+0.0869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1348
_reflns_number_total             1862
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ka1296.cif
_cod_data_source_block           LRSA0261
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        848.8(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008794
loop_
_symmetry_equiv_pos_as_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'
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_group
_atom_site_type_symbol
O1 0.2747(3) 0.03367(9) 0.06784(10) 0.0542(4) Uani d . 1 . O
N2 0.0812(3) -0.10767(11) 0.14324(12) 0.0462(4) Uani d . 1 . N
N3 -0.0480(3) 0.06930(13) 0.16448(13) 0.0554(4) Uani d . 1 . N
C1 0.1117(3) 0.00308(13) 0.12203(12) 0.0437(4) Uani d . 1 . C
C2 0.2171(3) -0.19204(12) 0.10778(12) 0.0408(4) Uani d . 1 . C
C3 0.1764(4) -0.30024(13) 0.13619(14) 0.0475(4) Uani d . 1 . C
C4 0.3212(4) -0.38220(14) 0.10011(15) 0.0551(5) Uani d . 1 . C
C5 0.5080(4) -0.35846(14) 0.03622(16) 0.0568(5) Uani d . 1 . C
C6 0.5383(4) -0.25292(14) 0.00802(15) 0.0515(5) Uani d . 1 . C
N1 0.3945(3) -0.17305(11) 0.04434(11) 0.0450(4) Uani d . 1 . N
N4 -0.3984(3) -0.13603(12) 0.31473(11) 0.0502(4) Uani d . 1 . N
O2 -0.2617(3) -0.19858(11) 0.26988(12) 0.0711(5) Uani d . 1 . O
O3 -0.5530(3) -0.17421(14) 0.36844(12) 0.0771(5) Uani d . 1 . O
O4 -0.3794(4) -0.03581(12) 0.30350(14) 0.0833(6) Uani d . 1 . O
H3 0.050(4) -0.3146(16) 0.1809(14) 0.050 Uiso d . 1 . H
H4 0.294(4) -0.4541(18) 0.1185(13) 0.050 Uiso d . 1 . H
H5 0.615(4) -0.4109(17) 0.0151(14) 0.050 Uiso d . 1 . H
H6 0.660(4) -0.2251(16) -0.0334(15) 0.050 Uiso d . 1 . H
HN1 0.415(4) -0.1061(18) 0.0287(14) 0.050 Uiso d . 1 . H
HN2 -0.024(4) -0.1255(17) 0.1854(15) 0.050 Uiso d . 1 . H
HN32 -0.037(4) 0.142(2) 0.1572(13) 0.050 Uiso d . 1 . H
HN31 -0.162(4) 0.0464(16) 0.2038(15) 0.050 Uiso d . 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 0.0658(8) 0.0358(6) 0.0663(9) -0.0046(5) 0.0320(6) 0.0037(5)
N2 0.0530(8) 0.0352(7) 0.0549(9) -0.0020(6) 0.0266(7) 0.0024(6)
N3 0.0686(10) 0.0377(7) 0.0646(11) 0.0020(7) 0.0292(8) -0.0011(7)
C1 0.0500(9) 0.0354(7) 0.0475(10) -0.0029(7) 0.0133(7) 0.0007(6)
C2 0.0435(8) 0.0355(7) 0.0450(9) -0.0044(6) 0.0124(7) -0.0008(6)
C3 0.0533(9) 0.0383(8) 0.0544(11) -0.0061(7) 0.0212(8) 0.0027(7)
C4 0.0677(11) 0.0322(8) 0.0688(13) -0.0047(7) 0.0227(9) 0.0010(8)
C5 0.0648(11) 0.0357(8) 0.0748(13) 0.0009(8) 0.0295(10) -0.0060(8)
C6 0.0557(10) 0.0409(8) 0.0628(12) -0.0032(7) 0.0285(9) -0.0030(8)
N1 0.0526(8) 0.0326(6) 0.0533(9) -0.0039(6) 0.0217(6) 0.0017(6)
N4 0.0538(8) 0.0460(7) 0.0541(9) -0.0071(6) 0.0216(7) -0.0005(6)
O2 0.0850(10) 0.0488(7) 0.0882(12) -0.0011(7) 0.0504(8) -0.0036(7)
O3 0.0813(10) 0.0732(10) 0.0855(12) -0.0130(8) 0.0496(9) 0.0053(8)
O4 0.1002(12) 0.0443(7) 0.1152(14) -0.0003(8) 0.0567(11) 0.0016(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
H H 0.0000 0.0000 '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
C2 N2 C1 125.93(14) yes
C2 N2 HN2 115.4(14) no
C1 N2 HN2 118.5(14) no
C1 N3 HN32 120.4(13) no
C1 N3 HN31 123.6(13) no
HN32 N3 HN31 115.9(18) no
O1 C1 N3 124.50(16) yes
O1 C1 N2 121.18(15) yes
N3 C1 N2 114.32(15) yes
N1 C2 N2 120.39(14) yes
N1 C2 C3 118.35(15) yes
N2 C2 C3 121.26(15) yes
C4 C3 C2 119.22(16) no
C4 C3 H3 121.8(12) no
C2 C3 H3 119.0(12) no
C3 C4 C5 120.51(16) no
C3 C4 H4 119.4(12) no
C5 C4 H4 120.0(12) no
C6 C5 C4 118.90(17) no
C6 C5 H5 119.1(12) no
C4 C5 H5 121.9(12) no
N1 C6 C5 119.86(17) no
N1 C6 H6 112.3(12) no
C5 C6 H6 127.8(12) no
C2 N1 C6 123.12(14) no
C2 N1 HN1 116.1(13) no
C6 N1 HN1 120.8(13) no
O3 N4 O4 120.93(16) no
O3 N4 O2 119.70(15) no
O4 N4 O2 119.36(14) no
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 C1 . 1.2300(19) yes
N2 C2 . 1.359(2) yes
N2 C1 . 1.394(2) yes
N2 HN2 . 0.86(2) no
N3 C1 . 1.324(2) yes
N3 HN32 . 0.89(2) no
N3 HN31 . 0.88(2) no
C2 N1 . 1.340(2) no
C2 C3 . 1.398(2) no
C3 C4 . 1.366(3) no
C3 H3 . 0.95(2) no
C4 C5 . 1.392(3) no
C4 H4 . 0.93(2) no
C5 C6 . 1.358(3) no
C5 H5 . 0.91(2) no
C6 N1 . 1.346(2) no
C6 H6 . 0.95(2) no
N1 HN1 . 0.85(2) no
N4 O3 . 1.2265(19) yes
N4 O4 . 1.237(2) yes
N4 O2 . 1.2400(19) yes
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 HN1 O1 . 0.85(2) 1.95(2) 2.6221(19) 135.1(18) yes
N1 HN1 O1 3_655 0.85(2) 2.34(2) 2.9417(18) 127.9(17) yes
N2 HN2 O2 . 0.86(2) 1.97(2) 2.820(2) 168(2) yes
N3 HN31 O4 . 0.88(2) 2.10(2) 2.971(2) 168.0(17) yes
N3 HN32 O3 2_455 0.89(2) 2.33(2) 3.210(2) 171.7(17) yes
N3 HN32 O2 2_455 0.89(2) 2.47(2) 3.155(2) 134.8(16) 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_publ_flag
C2 N2 C1 O1 -1.0(3) no
C2 N2 C1 N3 178.79(17) no
C1 N2 C2 N1 -1.9(3) no
C1 N2 C2 C3 178.05(18) no
N1 C2 C3 C4 1.2(3) no
N2 C2 C3 C4 -178.74(17) no
C2 C3 C4 C5 0.4(3) no
C3 C4 C5 C6 -2.0(3) no
C4 C5 C6 N1 2.1(3) no
N2 C2 N1 C6 178.80(17) no
C3 C2 N1 C6 -1.1(3) no
C5 C6 N1 C2 -0.5(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136246
