#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007122.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_2007122
loop_
_publ_author_name
'Angelova, O.'
'Petrova, R.'
'Atanasov, V.'
_publ_section_title
;
 2-(Nitroamino)pyridine
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              441
_journal_page_last               442
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C5 H5 N3 O2'
_chemical_formula_sum            'C5 H5 N3 O2'
_chemical_formula_weight         139.11
_chemical_melting_point          190
_chemical_name_systematic        2-(nitramino)pyridine
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_type_scat_source           'SDP/PDP (Enraf-Nonius, 1985)'
_audit_creation_method           'KAPPA (Macicek, 1992. Unpublished)'
_cell_angle_alpha                90
_cell_angle_beta                 98.43(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.331(4)
_cell_length_b                   3.678(3)
_cell_length_c                   17.0520(10)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    292
_cell_measurement_theta_max      22.25
_cell_measurement_theta_min      21.54
_cell_volume                     1137.2(10)
_computing_data_collection
'CAD-4 diffractometer software (Enraf-Nonius, 1988)'
_computing_data_reduction        'SDP/PDP (Enraf-Nonius, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'KAPPA (Mac\'i\<cek, 1992)'
_computing_structure_refinement  SDP/PDP
_computing_structure_solution    'MULTAN11/82 (Main et al., 1982)'
_diffrn_ambient_temperature      292
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6136
_diffrn_reflns_theta_max         30.0
_diffrn_standards_decay_%        '1.6 '
_diffrn_standards_interval_count 500
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.12
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      not_measured
_exptl_crystal_density_method    none
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.095
_refine_ls_extinction_coef       3.976E-6(6)
_refine_ls_extinction_method     'Stout & Jensen (1968) formula 17.16'
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    H_atoms:_see_below
_refine_ls_matrix_type           full
_refine_ls_number_constraints    12
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1220
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.018
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + (0.045*F)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.071
_reflns_number_gt                1220
_reflns_number_total             1692
_reflns_threshold_expression     'I > 3\s(I)'
_[local]_cod_data_source_file    sk1128.cif
_[local]_cod_data_source_block   LRSA0244
_[local]_cod_cif_authors_sg_H-M  'I 2/a'
_cod_original_cell_volume        1137.3(7)
_cod_database_code               2007122
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2+x,-y,+z
1/2+x,1/2+y,1/2+z
+x,1/2-y,1/2+z
-x,-y,-z
1/2-x,+y,-z
1/2-x,1/2-y,1/2-z
-x,1/2+y,1/2-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_calc_attached_atom
O1 0.41131(6) -0.1925(4) 0.15292(7) 0.0545(3) Uani ? ?
O2 0.31355(7) 0.0426(4) 0.08584(7) 0.0601(3) Uani ? ?
N1 0.31503(6) 0.0694(3) 0.34356(6) 0.0311(2) Uani ? ?
N2 0.32041(6) 0.0516(4) 0.21382(6) 0.0342(3) Uani ? ?
N3 0.35095(7) -0.0373(4) 0.14993(7) 0.0378(3) Uani ? ?
C2 0.35668(7) -0.0279(3) 0.28721(7) 0.0281(3) Uani ? ?
C3 0.42603(7) -0.1823(4) 0.31444(8) 0.0339(3) Uani ? ?
C4 0.44784(8) -0.2285(4) 0.39414(9) 0.0391(3) Uani ? ?
C5 0.40256(8) -0.1269(4) 0.44970(9) 0.0412(4) Uani ? ?
C6 0.33611(8) 0.0230(5) 0.42173(8) 0.0375(3) Uani ? ?
H3 0.4575 -0.2528 0.2776 0.0506 Uiso calc C3
H4 0.4945 -0.3336 0.4125 0.0506 Uiso calc C4
H5 0.4176 -0.1612 0.5049 0.0506 Uiso calc C5
H6 0.3041 0.0963 0.4580 0.0506 Uiso calc C6
HN1 0.2720(10) 0.200(7) 0.3230(10) 0.0506 Uiso ? N1
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 0.0408(5) 0.0810(8) 0.0451(5) 0.0192(5) 0.0173(4) -0.0055(6)
O2 0.0576(6) 0.0954(9) 0.0285(5) 0.0234(6) 0.0106(4) 0.0051(6)
N1 0.0286(4) 0.0373(5) 0.0284(5) 0.0015(4) 0.0073(4) -0.0005(5)
N2 0.0321(5) 0.0451(6) 0.0271(5) 0.0062(5) 0.0104(4) 0.0000(5)
N3 0.0356(5) 0.0476(6) 0.0323(5) 0.0034(5) 0.0124(4) -0.0004(5)
C2 0.0282(5) 0.0277(5) 0.0295(5) -0.0015(4) 0.0082(4) -0.0005(5)
C3 0.0293(5) 0.0346(6) 0.0385(7) 0.0022(5) 0.0067(5) -0.0004(6)
C4 0.0337(6) 0.0386(7) 0.0437(7) 0.0033(6) 0.0009(5) 0.0052(6)
C5 0.0434(7) 0.0455(8) 0.0336(6) -0.0016(6) 0.0021(5) 0.0056(6)
C6 0.0404(6) 0.0453(7) 0.0283(6) -0.0024(6) 0.0093(5) -0.0008(6)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
O 0.008 0.006
N 0.004 0.003
C 0.002 0.002
H 0.000 0.000
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
C2 N1 C6 1 1 123.90(10) no
C2 N1 HN1 1 1 114.0(10) no
C6 N1 HN1 1 1 122.0(10) no
N3 N2 C2 1 1 119.40(10) yes
O1 N3 O2 1 1 121.40(10) yes
O1 N3 N2 1 1 123.90(10) yes
O2 N3 N2 1 1 114.70(10) yes
N1 C2 N2 1 1 110.10(10) yes
N1 C2 C3 1 1 116.50(10) no
N2 C2 C3 1 1 133.30(10) no
C2 C3 C4 1 1 119.70(10) no
C2 C3 H3 1 1 120.01 no
C4 C3 H3 1 1 120.28 no
C3 C4 C5 1 1 121.50(10) no
C3 C4 H4 1 1 119.80 no
C5 C4 H4 1 1 118.67 no
C4 C5 C6 1 1 117.50(10) no
C4 C5 H5 1 1 121.35 no
C6 C5 H5 1 1 121.18 no
N1 C6 C5 1 1 120.80(10) no
N1 C6 H6 1 1 119.67 no
C5 C6 H6 1 1 119.49 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 N3 1 1.239(2) yes
O2 N3 1 1.237(2) yes
N1 C2 1 1.360(2) yes
N1 C6 1 1.343(2) yes
N1 HN1 1 0.94(2) no
N2 N3 1 1.336(2) yes
N2 C2 1 1.360(2) yes
C2 C3 1 1.407(2) yes
C3 C4 1 1.370(2) yes
C3 H3 1 0.950 no
C4 C5 1 1.399(2) yes
C4 H4 1 0.949 no
C5 C6 1 1.358(2) yes
C5 H5 1 0.950 no
C6 H6 1 0.951 no
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 N2 7_555 0.95(2) 1.95(2) 2.890(3) 175.7(18) yes
C3 H3 O1 1_555 0.95 2.18 2.728(2) 115.4 yes
C4 H4 O1 8_645 0.95 2.56 3.291(2) 134.3 yes
C5 H5 O1 4_545 0.95 2.60 3.509(2) 160.3 yes
C6 H6 O2 4_555 0.95 2.54 3.300(2) 137.5 yes
C6 H6 O2 7_555 0.95 2.55 3.161(2) 122.1 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
C6 N1 C2 N2 179.70(10) no
C6 N1 C2 C3 -0.6(2) no
C2 N1 C6 C5 0.3(2) no
C2 N2 N3 O1 0.4(2) no
C2 N2 N3 O2 179.30(10) no
N3 N2 C2 N1 -177.30(10) no
N3 N2 C2 C3 3.2(2) no
N1 C2 C3 C4 0.3(2) no
N2 C2 C3 C4 179.90(10) no
C2 C3 C4 C5 0.3(2) no
C3 C4 C5 C6 -0.6(2) no
C4 C5 C6 N1 0.3(2) no