#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/63/2236314.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_2236314
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Arana, Carolina'
'De Simone, Carlos A.'
_publ_section_title
;
 Redetermination of 4-cyanopyridine N-oxide
;
_journal_coeditor_code           HG5244
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2805
_journal_paper_doi               10.1107/S1600536812036690
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H4 N2 O'
_chemical_formula_moiety         'C6 H4 N2 O'
_chemical_formula_sum            'C6 H4 N2 O'
_chemical_formula_weight         120.11
_chemical_melting_point          496.0(10)
_chemical_name_common            '4-cyanopyridine N-oxide'
_chemical_name_systematic
;
4-cyanopyridine N-oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.973(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8743(8)
_cell_length_b                   6.0582(6)
_cell_length_c                   11.6278(10)
_cell_measurement_reflns_used    7553
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_volume                     554.36(9)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4336
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale-green
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0568
_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)+(0.1003P)²+0.0643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                964
_reflns_number_total             1224
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5244.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236314
_cod_database_fobs_code          2236314
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.62819(15) 0.2012(2) 0.91581(10) 0.0456(4) Uani d . 1 1
O O1 0.54449(17) 0.3499(2) 0.85653(10) 0.0671(5) Uani d . 1 1
C C4 0.7599(2) 0.0848(3) 1.09136(14) 0.0500(4) Uani d . 1 1
H H4 0.7885 0.1123 1.1683 0.060 Uiso calc R 1 1
C C6 0.90575(19) -0.2718(2) 1.10517(13) 0.0482(4) Uani d . 1 1
N N2 0.9834(2) -0.4015(2) 1.15568(14) 0.0656(5) Uani d . 1 1
C C3 0.80898(17) -0.1108(2) 1.04066(12) 0.0427(4) Uani d . 1 1
C C2 0.7643(2) -0.1471(3) 0.92614(13) 0.0500(4) Uani d . 1 1
H H2 0.7958 -0.2775 0.8905 0.060 Uiso calc R 1 1
C C5 0.6695(2) 0.2377(3) 1.02802(13) 0.0504(4) Uani d . 1 1
H H5 0.6360 0.3683 1.0626 0.061 Uiso calc R 1 1
C C1 0.6735(2) 0.0094(2) 0.86553(13) 0.0523(5) Uani d . 1 1
H H1 0.6426 -0.0162 0.7888 0.063 Uiso calc R 1 1
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
N1 0.0492(7) 0.0422(7) 0.0449(7) 0.0025(5) -0.0066(5) 0.0031(5)
O1 0.0830(9) 0.0573(8) 0.0596(7) 0.0187(6) -0.0172(6) 0.0103(6)
C4 0.0580(9) 0.0493(9) 0.0422(8) 0.0037(7) -0.0078(7) -0.0040(6)
C6 0.0508(8) 0.0445(8) 0.0489(8) 0.0025(6) -0.0047(7) 0.0019(7)
N2 0.0726(10) 0.0572(9) 0.0660(10) 0.0104(7) -0.0116(7) 0.0040(7)
C3 0.0415(7) 0.0410(8) 0.0454(8) -0.0015(5) -0.0019(6) 0.0038(6)
C2 0.0576(9) 0.0429(8) 0.0491(9) 0.0032(6) -0.0029(7) -0.0055(6)
C5 0.0607(9) 0.0435(8) 0.0465(8) 0.0057(7) -0.0071(7) -0.0057(6)
C1 0.0643(10) 0.0504(9) 0.0417(8) 0.0030(7) -0.0079(7) -0.0044(7)
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 119.96(13)
O1 N1 C1 120.14(13)
C5 N1 C1 119.90(13)
C5 C4 C3 119.86(14)
C5 C4 H4 120.1
C3 C4 H4 120.1
N2 C6 C3 179.31(16)
C2 C3 C4 118.71(14)
C2 C3 C6 120.58(13)
C4 C3 C6 120.71(13)
C1 C2 C3 119.79(14)
C1 C2 H2 120.1
C3 C2 H2 120.1
N1 C5 C4 120.84(14)
N1 C5 H5 119.6
C4 C5 H5 119.6
N1 C1 C2 120.87(14)
N1 C1 H1 119.6
C2 C1 H1 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.2997(15)
N1 C5 1.3520(19)
N1 C1 1.354(2)
C4 C5 1.368(2)
C4 C3 1.385(2)
C4 H4 0.9300
C6 N2 1.1453(19)
C6 C3 1.4336(19)
C3 C2 1.383(2)
C2 C1 1.368(2)
C2 H2 0.9300
C5 H5 0.9300
C1 H1 0.9300
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
C1 H1 O1 2_646 0.93 2.35 3.200(2) 152.3
C5 H5 O1 3_667 0.93 2.43 3.323(2) 160.6
C2 H2 N2 3_747 0.93 2.68 3.530(2) 153.1
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
C5 C4 C3 C2 -0.2(2)
C5 C4 C3 C6 179.17(14)
N2 C6 C3 C4 -167(14)
C4 C3 C2 C1 0.1(2)
C6 C3 C2 C1 -179.26(14)
O1 N1 C5 C4 -178.92(14)
C1 N1 C5 C4 1.4(2)
C3 C4 C5 N1 -0.5(3)
O1 N1 C1 C2 178.83(15)
C5 N1 C1 C2 -1.4(2)
C3 C2 C1 N1 0.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 76394
