#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/87/2008788.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_2008788
loop_
_publ_author_name
'Zaleski, Jacek'
'Daszkiewicz, Zdzisław'
'Kyzioł, Janusz B.'
_publ_section_title
;
 4-(N-Methylnitramino)pyridine 1-oxide
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1292
_journal_page_last               1295
_journal_paper_doi               10.1107/S0108270199004552
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C6 H7 N3 O3'
_chemical_formula_weight         169.15
_chemical_name_systematic
;
 4-(N-Methylnitramino)-pyridine 1-oxide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.756(3)
_cell_length_b                   6.8700(10)
_cell_length_c                   15.740(3)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    90.00(10)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      18
_cell_volume                     1379.4(5)
_computing_cell_refinement       'Kuma Diffraction Software (Kuma, 1997)'
_computing_data_reduction        'Kuma Diffraction Software'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.755
_diffrn_measured_fraction_theta_max 0.755
_diffrn_measurement_device_type  'Kuma KM-4 diffractometer'
_diffrn_measurement_method       ω-θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1757
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.87
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        0.32
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0066P)²+6.7646P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                1183
_reflns_number_total             1757
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1027.cif
_cod_data_source_block           1_at_90_K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0066P)^2^+6.7646P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0066P)^2^+6.7646P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               2008788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.37956(17) 0.2110(3) 0.51814(15) 0.0171(5) Uani d . 1 . . O
N1 0.2860(2) 0.2321(4) 0.55015(16) 0.0130(5) Uani d . 1 . . N
C2 0.2743(2) 0.3028(4) 0.6305(2) 0.0129(6) Uani d . 1 . . C
C3 0.1766(2) 0.3244(4) 0.6659(2) 0.0134(6) Uani d . 1 . . C
C4 0.0887(2) 0.2740(4) 0.6184(2) 0.0117(6) Uani d . 1 . . C
C5 0.1008(2) 0.2037(4) 0.5367(2) 0.0127(6) Uani d . 1 . . C
C6 0.2001(2) 0.1838(4) 0.5036(2) 0.0134(6) Uani d . 1 . . C
N7 -0.0131(2) 0.3087(4) 0.65405(17) 0.0128(5) Uani d . 1 . . N
N8 -0.0798(2) 0.1559(4) 0.65894(17) 0.0136(5) Uani d . 1 . . N
O9 -0.04386(18) -0.0094(3) 0.64919(15) 0.0169(5) Uani d . 1 . . O
O10 -0.17175(17) 0.1924(4) 0.67684(15) 0.0184(5) Uani d . 1 . . O
C11 -0.0585(3) 0.5049(5) 0.6559(2) 0.0160(6) Uani d . 1 . . C
H6 0.215(3) 0.136(5) 0.447(2) 0.005(8) Uiso d . 1 . . H
H3 0.167(3) 0.389(5) 0.729(2) 0.007(8) Uiso d . 1 . . H
H5 0.040(3) 0.175(5) 0.503(2) 0.011(9) Uiso d . 1 . . H
H2 0.341(3) 0.327(5) 0.660(2) 0.015(9) Uiso d . 1 . . H
H11A -0.111(3) 0.519(7) 0.609(3) 0.029(12) Uiso d . 1 . . H
H11B -0.084(3) 0.521(6) 0.716(3) 0.027(11) Uiso d . 1 . . H
H11C -0.002(4) 0.578(7) 0.646(3) 0.039(14) 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 0.0097(10) 0.0177(11) 0.0224(12) 0.0006(9) 0.0027(9) -0.0011(10)
N1 0.0139(12) 0.0094(11) 0.0151(13) 0.0008(10) 0.0016(10) 0.0014(10)
C2 0.0132(14) 0.0106(12) 0.0144(14) 0.0000(11) -0.0022(11) 0.0002(11)
C3 0.0136(14) 0.0113(12) 0.0148(15) -0.0012(11) -0.0013(12) 0.0031(12)
C4 0.0090(12) 0.0091(12) 0.0168(15) 0.0008(10) 0.0006(11) 0.0018(11)
C5 0.0123(14) 0.0110(12) 0.0143(15) -0.0004(11) -0.0032(11) 0.0009(12)
C6 0.0148(14) 0.0103(12) 0.0148(15) 0.0001(11) 0.0007(12) -0.0006(12)
N7 0.0119(12) 0.0107(11) 0.0152(13) -0.0002(10) 0.0013(10) -0.0007(10)
N8 0.0155(12) 0.0128(11) 0.0117(13) -0.0015(10) -0.0008(10) 0.0023(10)
O9 0.0202(11) 0.0100(9) 0.0196(12) -0.0005(9) 0.0037(10) -0.0005(9)
O10 0.0132(11) 0.0203(11) 0.0201(12) -0.0009(9) 0.0048(9) 0.0008(10)
C11 0.0163(15) 0.0100(12) 0.0214(18) 0.0021(12) 0.0012(13) 0.0000(13)
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
O1 N1 C6 120.2(3)
O1 N1 C2 119.9(3)
C6 N1 C2 119.9(3)
N1 C2 C3 120.9(3)
C2 C3 C4 119.2(3)
C5 C4 C3 119.7(3)
C5 C4 N7 121.6(3)
C3 C4 N7 118.6(3)
C6 C5 C4 119.4(3)
N1 C6 C5 120.9(3)
N8 N7 C4 117.5(2)
N8 N7 C11 117.5(2)
C4 N7 C11 121.2(3)
O10 N8 O9 124.7(3)
O10 N8 N7 117.0(3)
O9 N8 N7 118.2(3)
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 N1 . 1.304(3) ?
N1 C6 . 1.359(4) ?
N1 C2 . 1.364(4) ?
C2 C3 . 1.372(4) ?
C3 C4 . 1.391(4) ?
C4 C5 . 1.382(4) ?
C4 N7 . 1.434(4) ?
C5 C6 . 1.376(4) ?
N7 N8 . 1.354(4) ?
N7 C11 . 1.467(4) ?
N8 O10 . 1.232(3) ?
N8 O9 . 1.234(3) ?
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
C3 H3 O9 3_556 1.10(3) 2.57(3) 3.556(4) 148(2) ?
C3 H3 O10 3_556 1.10(3) 2.55(3) 3.539(4) 148(2) ?
C5 H5 O1 4_456 0.97(3) 2.21(3) 3.009(4) 139(3) 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
O1 N1 C2 C3 -179.3(3)
C6 N1 C2 C3 0.7(4)
N1 C2 C3 C4 -0.3(5)
C2 C3 C4 C5 -0.2(4)
C2 C3 C4 N7 -176.1(3)
C3 C4 C5 C6 0.3(5)
N7 C4 C5 C6 176.1(3)
O1 N1 C6 C5 179.5(3)
C2 N1 C6 C5 -0.6(4)
C4 C5 C6 N1 0.1(5)
C5 C4 N7 N8 59.0(4)
C3 C4 N7 N8 -125.2(3)
C5 C4 N7 C11 -98.9(4)
C3 C4 N7 C11 77.0(4)
C4 N7 N8 O10 -168.9(3)
C11 N7 N8 O10 -10.2(4)
C4 N7 N8 O9 14.4(4)
C11 N7 N8 O9 173.1(3)
