#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/71/2007122.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, Olyana'
'Petrova, Rosica'
'Atanasov, Vladimir'
_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 Unpublished)'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 .41131(6) -.1925(4) .15292(7) .0545(3) Uani ? ?
O2 .31355(7) .0426(4) .08584(7) .0601(3) Uani ? ?
N1 .31503(6) .0694(3) .34356(6) .0311(2) Uani ? ?
N2 .32041(6) .0516(4) .21382(6) .0342(3) Uani ? ?
N3 .35095(7) -.0373(4) .14993(7) .0378(3) Uani ? ?
C2 .35668(7) -.0279(3) .28721(7) .0281(3) Uani ? ?
C3 .42603(7) -.1823(4) .31444(8) .0339(3) Uani ? ?
C4 .44784(8) -.2285(4) .39414(9) .0391(3) Uani ? ?
C5 .40256(8) -.1269(4) .44970(9) .0412(4) Uani ? ?
C6 .33611(8) .0230(5) .42173(8) .0375(3) Uani ? ?
H3 .4575 -.2528 .2776 .0506 Uiso calc C3
H4 .4945 -.3336 .4125 .0506 Uiso calc C4
H5 .4176 -.1612 .5049 .0506 Uiso calc C5
H6 .3041 .0963 .4580 .0506 Uiso calc C6
HN1 .2720(10) .200(7) .3230(10) .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 .0408(5) .0810(8) .0451(5) .0192(5) .0173(4) -.0055(6)
O2 .0576(6) .0954(9) .0285(5) .0234(6) .0106(4) .0051(6)
N1 .0286(4) .0373(5) .0284(5) .0015(4) .0073(4) -.0005(5)
N2 .0321(5) .0451(6) .0271(5) .0062(5) .0104(4) .0000(5)
N3 .0356(5) .0476(6) .0323(5) .0034(5) .0124(4) -.0004(5)
C2 .0282(5) .0277(5) .0295(5) -.0015(4) .0082(4) -.0005(5)
C3 .0293(5) .0346(6) .0385(7) .0022(5) .0067(5) -.0004(6)
C4 .0337(6) .0386(7) .0437(7) .0033(6) .0009(5) .0052(6)
C5 .0434(7) .0455(8) .0336(6) -.0016(6) .0021(5) .0056(6)
C6 .0404(6) .0453(7) .0283(6) -.0024(6) .0093(5) -.0008(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_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 .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 .950 no
C4 C5 . 1 1.399(2) yes
C4 H4 . 1 .949 no
C5 C6 . 1 1.358(2) yes
C5 H5 . 1 .950 no
C6 H6 . 1 .951 no
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_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
_journal_paper_doi 10.1107/S0108270197015503