#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/81/2008146.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_2008146
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Valderrama-Naranjo, Jaime'
'Montaño, Angela Marcela'
_publ_section_title
;
 A 1:1 complex of 4-nitropyridine N-oxide and 3-hydroxybenzoic
 acid
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              218
_journal_page_last               220
_journal_paper_doi               10.1107/S0108270198009949
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C5 H4 N2 O3 . C7 H6 O3'
_chemical_formula_sum            'C12 H10 N2 O6'
_chemical_formula_weight         278.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.46(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5453(6)
_cell_length_b                   7.5995(8)
_cell_length_c                   24.855(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      9.9
_cell_volume                     1230.7(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'SDP (Frenz, 1978)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1995)'
_computing_publication_material  SDP
_computing_structure_refinement  SHELXL93
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.035
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2719
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0.70
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.12
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale_yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.167
_refine_ls_extinction_coef       0.054(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.114
_refine_ls_goodness_of_fit_obs   1.028
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_restrained_S_obs      1.028
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/(σ²(Fo²)+(0.0306P)²+0.6014P) where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.117
_refine_ls_wR_factor_obs         0.084
_reflns_number_observed          1613
_reflns_number_total             2495
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            fr1126.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w =
1/(\s^2^(Fo^2^)+(0.0306P)^2^+0.6014P) 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^)+(0.0306P)^2^+0.6014P) 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      'P 21/n'
_cod_database_code               2008146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 -0.2038(3) 0.6422(2) 0.23714(7) 0.0647(5) Uani d . 1 . O
O2 -0.7565(3) 0.2264(3) 0.06711(7) 0.0654(5) Uani d . 1 . O
O3 -0.9418(3) 0.2184(3) 0.13452(8) 0.0697(6) Uani d . 1 . O
N1 -0.3415(3) 0.5492(2) 0.20792(8) 0.0485(5) Uani d . 1 . N
N2 -0.7865(3) 0.2601(3) 0.11371(8) 0.0492(5) Uani d . 1 . N
C1 -0.3056(4) 0.4979(3) 0.15750(10) 0.0499(6) Uani d . 1 . C
H1 -0.1825 0.5281 0.14405 0.076 Uiso calc R 1 . H
C2 -0.4483(3) 0.4024(3) 0.12616(9) 0.0463(6) Uani d . 1 . C
H2 -0.4236 0.3671 0.09154 0.076 Uiso calc R 1 . H
C3 -0.6291(3) 0.3596(3) 0.14686(8) 0.0414(5) Uani d . 1 . C
C4 -0.6655(4) 0.4100(3) 0.19819(9) 0.0487(6) Uani d . 1 . C
H4 -0.7873 0.3794 0.21223 0.076 Uiso calc R 1 . H
C5 -0.5193(4) 0.5059(3) 0.22820(9) 0.0531(6) Uani d . 1 . C
H5 -0.5424 0.5416 0.26290 0.076 Uiso calc R 1 . H
O4 0.0792(3) 0.4581(2) 0.29551(6) 0.0513(4) Uani d . 1 . O
HO4 -0.033(4) 0.521(4) 0.2779(11) 0.076 Uiso d . 1 . H
O5 0.4614(2) 0.0989(2) 0.43939(6) 0.0520(4) Uani d . 1 . O
O6 0.2740(3) 0.1174(3) 0.50932(6) 0.0620(5) Uani d . 1 . O
HO6 0.380(4) 0.037(4) 0.5283(11) 0.076 Uiso d . 1 . H
C6 0.3091(3) 0.1556(3) 0.46043(8) 0.0415(5) Uani d . 1 . C
C7 0.1550(3) 0.2674(3) 0.42947(8) 0.0373(5) Uani d . 1 . C
C8 -0.0243(3) 0.3165(3) 0.45133(9) 0.0459(6) Uani d . 1 . C
H8 -0.0452 0.2853 0.48656 0.076 Uiso calc R 1 . H
C9 -0.1711(3) 0.4123(3) 0.42013(9) 0.0490(6) Uani d . 1 . C
H9 -0.2914 0.4453 0.43455 0.076 Uiso calc R 1 . H
C10 -0.1412(3) 0.4594(3) 0.36786(9) 0.0432(5) Uani d . 1 . C
H10 -0.2418 0.5223 0.34703 0.076 Uiso calc R 1 . H
C11 0.0398(3) 0.4127(3) 0.34639(8) 0.0381(5) Uani d . 1 . C
C12 0.1878(3) 0.3169(3) 0.37719(8) 0.0375(5) Uani d . 1 . C
H12 0.3090 0.2857 0.36293 0.076 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -3 -6
-3 1 4
-1 2 -9
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C5 119.8(2) yes
O1 N1 C1 119.8(2) yes
C5 N1 C1 120.4(2) yes
O2 N2 O3 124.1(2) ?
O2 N2 C3 118.3(2) ?
O3 N2 C3 117.6(2) ?
N1 C1 C2 120.7(2) ?
N1 C1 H1 119.6 ?
C2 C1 H1 119.6 ?
C1 C2 C3 118.6(2) ?
C1 C2 H2 120.7 ?
C3 C2 H2 120.7 ?
C2 C3 C4 120.9(2) ?
C2 C3 N2 119.7(2) ?
C4 C3 N2 119.4(2) ?
C5 C4 C3 118.8(2) ?
C5 C4 H4 120.6 ?
C3 C4 H4 120.6 ?
N1 C5 C4 120.6(2) ?
N1 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C11 O4 HO4 110.5(17) ?
C6 O6 HO6 113.7(15) yes
O5 C6 O6 122.6(2) yes
O5 C6 C7 120.9(2) yes
O6 C6 C7 116.5(2) yes
C12 C7 C8 120.3(2) yes
C12 C7 C6 119.0(2) yes
C8 C7 C6 120.7(2) yes
C9 C8 C7 119.3(2) ?
C9 C8 H8 120.4 ?
C7 C8 H8 120.4 ?
C10 C9 C8 120.8(2) ?
C10 C9 H9 119.6 ?
C8 C9 H9 119.6 ?
C9 C10 C11 119.8(2) ?
C9 C10 H10 120.1 ?
C11 C10 H10 120.1 ?
O4 C11 C12 117.6(2) yes
O4 C11 C10 122.4(2) yes
C12 C11 C10 119.9(2) yes
C11 C12 C7 119.9(2) ?
C11 C12 H12 120.1 ?
C7 C12 H12 120.1 ?
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 . 1.310(2) yes
O2 N2 . 1.221(2) ?
O3 N2 . 1.225(2) ?
N1 C5 . 1.353(3) yes
N1 C1 . 1.354(3) yes
N2 C3 . 1.467(3) yes
C1 C2 . 1.367(3) ?
C1 H1 . 0.93 ?
C2 C3 . 1.373(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.374(3) ?
C4 C5 . 1.366(3) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
O4 C11 . 1.359(2) yes
O4 HO4 . 0.95(3) yes
O5 C6 . 1.246(3) yes
O6 C6 . 1.291(2) yes
O6 HO6 . 1.01(3) yes
C6 C7 . 1.478(3) yes
C7 C12 . 1.389(3) yes
C7 C8 . 1.390(3) yes
C8 C9 . 1.383(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.379(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.391(3) yes
C10 H10 . 0.93 ?
C11 C12 . 1.383(3) yes
C12 H12 . 0.93 ?
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 -179.3(2)
C5 N1 C1 C2 0.3(3)
N1 C1 C2 C3 0.1(3)
C1 C2 C3 C4 -0.6(3)
C1 C2 C3 N2 178.8(2)
O2 N2 C3 C2 -4.0(3)
O3 N2 C3 C2 177.0(2)
O2 N2 C3 C4 175.4(2)
O3 N2 C3 C4 -3.5(3)
C2 C3 C4 C5 0.9(4)
N2 C3 C4 C5 -178.6(2)
O1 N1 C5 C4 179.5(2)
C1 N1 C5 C4 -0.1(3)
C3 C4 C5 N1 -0.5(4)
O5 C6 C7 C12 -3.5(3)
O6 C6 C7 C12 178.2(2)
O5 C6 C7 C8 173.8(2)
O6 C6 C7 C8 -4.5(3)
C12 C7 C8 C9 1.2(3)
C6 C7 C8 C9 -176.1(2)
C7 C8 C9 C10 -0.1(4)
C8 C9 C10 C11 -1.0(4)
C9 C10 C11 O4 -178.8(2)
C9 C10 C11 C12 1.0(3)
O4 C11 C12 C7 179.9(2)
C10 C11 C12 C7 0.1(3)
C8 C7 C12 C11 -1.2(3)
C6 C7 C12 C11 176.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105661
