#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239273.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_2239273
loop_
_publ_author_name
'Peukert, Max'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Redetermination of 2-methyl-4-nitropyridine N-oxide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o426
_journal_page_last               o427
_journal_paper_doi               10.1107/S1600536814004450
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C6 H6 N2 O3'
_chemical_formula_moiety         'C6 H6 N2 O3'
_chemical_formula_sum            'C6 H6 N2 O3'
_chemical_formula_weight         154.13
_chemical_name_systematic
;
2-Methyl-4-nitropyridine N-oxide
;
_space_group_IT_number           57
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6775(7)
_cell_length_b                   12.4069(10)
_cell_length_c                   6.1995(5)
_cell_measurement_reflns_used    6590
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      34.98
_cell_measurement_theta_min      2.35
_cell_volume                     667.44(9)
_computing_cell_refinement       'SAINT-NT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-NT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19832
_diffrn_reflns_theta_full        30.39
_diffrn_reflns_theta_max         30.39
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.9319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.338
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1100
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0485
_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)+(0.0871P)²+0.2298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                973
_reflns_number_total             1100
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zp2011sup1.cif
_cod_data_source_block           I
_cod_database_code               2239273
_cod_database_fobs_code          2239273
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
O O1 0.52895(16) 0.30510(10) 0.2500 0.0309(3) Uani d S 1 2
O O2 1.05609(15) -0.02519(12) 0.2500 0.0355(4) Uani d S 1 2
O O3 0.85937(17) -0.13544(11) 0.2500 0.0441(4) Uani d S 1 2
N N1 0.61843(17) 0.22205(10) 0.2500 0.0223(3) Uani d S 1 2
N N2 0.91523(17) -0.04406(12) 0.2500 0.0276(3) Uani d S 1 2
C C1 0.55535(18) 0.12002(13) 0.2500 0.0216(3) Uani d S 1 2
C C2 0.65356(17) 0.03153(12) 0.2500 0.0203(3) Uani d S 1 2
H H2A 0.6128 -0.0395 0.2500 0.024 Uiso calc SR 1 2
C C3 0.81182(18) 0.04811(12) 0.2500 0.0214(3) Uani d S 1 2
C C4 0.87504(19) 0.15129(13) 0.2500 0.0249(3) Uani d S 1 2
H H4 0.9834 0.1621 0.2500 0.030 Uiso calc SR 1 2
C C5 0.77482(19) 0.23649(13) 0.2500 0.0247(3) Uani d S 1 2
H H5 0.8150 0.3077 0.2500 0.030 Uiso calc SR 1 2
C C6 0.38480(19) 0.11425(16) 0.2500 0.0283(4) Uani d SD 1 2
H H6A 0.3468(19) 0.1469(13) 0.133(2) 0.040(5) Uiso d D 1 1
H H6B 0.358(3) 0.0444(9) 0.2500 0.035(6) Uiso d SD 1 2
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 C5 119.48(14)
O1 N1 C1 119.61(14)
C5 N1 C1 120.91(13)
O3 N2 O2 123.99(15)
O3 N2 C3 118.73(14)
O2 N2 C3 117.28(14)
N1 C1 C2 118.79(14)
N1 C1 C6 116.16(14)
C2 C1 C6 125.05(15)
C3 C2 C1 119.30(14)
C3 C2 H2A 120.3
C1 C2 H2A 120.3
C2 C3 C4 121.72(14)
C2 C3 N2 119.61(14)
C4 C3 N2 118.68(14)
C5 C4 C3 117.36(15)
C5 C4 H4 121.3
C3 C4 H4 121.3
N1 C5 C4 121.92(14)
N1 C5 H5 119.0
C4 C5 H5 119.0
C1 C6 H6A 110.3(11)
C1 C6 H6B 108.0(16)
H6A C6 H6B 109.9(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2902(17)
O2 N2 1.244(2)
O3 N2 1.233(2)
N1 C5 1.369(2)
N1 C1 1.379(2)
N2 C3 1.454(2)
C1 C2 1.390(2)
C1 C6 1.482(2)
C2 C3 1.389(2)
C2 H2A 0.9500
C3 C4 1.393(2)
C4 C5 1.369(2)
C4 H4 0.9500
C5 H5 0.9500
C6 H6A 0.892(9)
C6 H6B 0.898(10)
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
C2 H2A O1 3_645 0.95 2.29 3.225(2) 169
C5 H5 O2 3_755 0.95 2.36 3.301(2) 173
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 C1 C2 180.0
C5 N1 C1 C2 0.0
O1 N1 C1 C6 0.0
C5 N1 C1 C6 180.0
N1 C1 C2 C3 0.0
C6 C1 C2 C3 180.0
C1 C2 C3 C4 0.0
C1 C2 C3 N2 180.0
O3 N2 C3 C2 0.0
O2 N2 C3 C2 180.0
O3 N2 C3 C4 180.0
O2 N2 C3 C4 0.0
C2 C3 C4 C5 0.0
N2 C3 C4 C5 180.0
O1 N1 C5 C4 180.0
C1 N1 C5 C4 0.0
C3 C4 C5 N1 0.0
