#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201066.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_2201066
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Montaño, Angela Marcela'
'Atencio, Reinaldo'
_publ_section_title
;
 The 1:1 complex of hydroquinone and 3-methy-4-nitropyridine 1-oxide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o623
_journal_page_last               o625
_journal_paper_doi               10.1107/S160053680200819X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C6 H6 O2, C6 H6 N2 O3'
_chemical_formula_moiety         'C6 H6 O2, C6 H6 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O5'
_chemical_formula_weight         264.24
_chemical_melting_point          384.0(10)
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.39(3)
_cell_angle_beta                 89.92(2)
_cell_angle_gamma                88.91(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8593(16)
_cell_length_b                   8.429(3)
_cell_length_c                   9.039(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      8
_cell_volume                     595.8(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and ZORTEP (Zsolnai, 1995)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_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  0.015
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2250
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange--red
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular_block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.221
_refine_ls_extinction_coef       0.034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.077P)²+0.1509P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.122
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                1848
_reflns_number_total             2091
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6173.cif
_cod_data_source_block           I
_cod_database_code               2201066
_cod_database_fobs_code          2201066
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 0.3953(2) 0.55619(19) 0.68901(18) 0.0419(4) Uani d . 1 . . C
H1 0.4661 0.4711 0.6696 0.050 Uiso calc . 1 . . H
C2 0.4149(2) 0.6282(2) 0.81648(18) 0.0421(4) Uani d . 1 . . C
H2 0.4973 0.5907 0.8856 0.051 Uiso calc . 1 . . H
C3 0.3119(2) 0.75697(19) 0.84251(17) 0.0381(4) Uani d . 1 . . C
C4 0.1868(2) 0.81540(18) 0.74227(18) 0.0374(4) Uani d . 1 . . C
C5 0.1717(2) 0.73451(19) 0.61632(18) 0.0395(4) Uani d . 1 . . C
H5 0.0886 0.7683 0.5465 0.047 Uiso calc . 1 . . H
C6 0.0674(2) 0.9538(2) 0.7568(2) 0.0536(5) Uani d . 1 . . C
H61 -0.0163 0.9587 0.6792 0.064 Uiso calc . 1 . . H
H62 0.1303 1.0509 0.7487 0.064 Uiso calc . 1 . . H
H63 0.0119 0.9406 0.8517 0.064 Uiso calc . 1 . . H
N1 0.27269(17) 0.60914(15) 0.59155(14) 0.0374(3) Uani d . 1 . . N
N2 0.3422(2) 0.82778(19) 0.98195(17) 0.0524(4) Uani d . 1 . . N
O1 0.25402(17) 0.53780(15) 0.46953(13) 0.0515(4) Uani d . 1 . . O
O2 0.2858(3) 0.9599(2) 0.99536(19) 0.0919(6) Uani d . 1 . . O
O3 0.4255(3) 0.7501(2) 1.07750(17) 0.0854(6) Uani d . 1 . . O
C7 -0.1063(2) 0.6283(2) 0.02089(19) 0.0456(4) Uani d . 1 . . C
H7 -0.1782 0.7146 0.0344 0.055 Uiso calc . 1 . . H
C8 0.0043(2) 0.5704(2) 0.13225(18) 0.0428(4) Uani d . 1 . . C
C9 -0.1105(2) 0.5577(2) -0.11172(18) 0.0447(4) Uani d . 1 . . C
H9 -0.1851 0.5970 -0.1868 0.054 Uiso calc . 1 . . H
C10 0.4654(2) 0.11298(18) 0.59675(17) 0.0398(4) Uani d . 1 . . C
H10 0.4426 0.1891 0.6623 0.048 Uiso calc . 1 . . H
C11 0.3716(2) 0.11380(18) 0.46727(18) 0.0386(4) Uani d . 1 . . C
C12 0.4074(2) -0.00009(19) 0.37064(17) 0.0409(4) Uani d . 1 . . C
H12 0.3453 -0.0004 0.2832 0.049 Uiso calc . 1 . . H
O4 0.0002(2) 0.64284(19) 0.26215(16) 0.0637(4) Uani d . 1 . . O
HO4 0.080(4) 0.605(3) 0.312(3) 0.087(9) Uiso d . 1 . . H
O5 0.24142(17) 0.22086(16) 0.43064(16) 0.0564(4) Uani d . 1 . . O
HO5 0.250(3) 0.306(3) 0.469(3) 0.063(6) Uiso d . 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
2 -1 1
1 -2 -1
0 -1 1
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
N1 C1 C2 . . 119.55(14) yes
N1 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C1 C2 C3 . . 119.77(15) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C2 C3 C4 . . 121.64(15) ?
C2 C3 N2 . . 116.19(15) ?
C4 C3 N2 . . 122.18(15) ?
C3 C4 C5 . . 115.54(15) ?
C3 C4 C6 . . 126.99(15) ?
C5 C4 C6 . . 117.47(15) ?
N1 C5 C4 . . 122.49(15) yes
N1 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
C4 C6 H61 . . 109.5 ?
C4 C6 H62 . . 109.5 ?
H61 C6 H62 . . 109.5 ?
C4 C6 H63 . . 109.5 ?
H61 C6 H63 . . 109.5 ?
H62 C6 H63 . . 109.5 ?
O1 N1 C5 . . 120.00(14) yes
O1 N1 C1 . . 119.01(13) yes
C5 N1 C1 . . 120.98(14) yes
O2 N2 O3 . . 123.45(16) ?
O2 N2 C3 . . 118.86(16) ?
O3 N2 C3 . . 117.68(16) ?
C8 C7 C9 . . 120.02(17) ?
C8 C7 H7 . . 120.0 ?
C9 C7 H7 . . 120.0 ?
O4 C8 C7 . . 117.43(17) yes
O4 C8 C9 . 2_565 122.79(16) yes
C7 C8 C9 . 2_565 119.76(17) ?
C8 C9 C7 2_565 . 120.22(16) ?
C8 C9 H9 2_565 . 119.9 ?
C7 C9 H9 . . 119.9 ?
C12 C10 C11 2_656 . 120.49(15) ?
C12 C10 H10 2_656 . 119.8 ?
C11 C10 H10 . . 119.8 ?
O5 C11 C10 . . 123.05(15) yes
O5 C11 C12 . . 117.85(14) yes
C10 C11 C12 . . 119.09(15) ?
C10 C12 C11 2_656 . 120.42(14) ?
C10 C12 H12 2_656 . 119.8 ?
C11 C12 H12 . . 119.8 ?
C8 O4 HO4 . . 106(2) yes
C11 O5 HO5 . . 113.9(16) yes
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
C1 N1 . 1.346(2) yes
C1 C2 . 1.364(2) ?
C1 H1 . 0.930 ?
C2 C3 . 1.380(2) ?
C2 H2 . 0.930 ?
C3 C4 . 1.388(2) ?
C3 N2 . 1.468(2) ?
C4 C5 . 1.389(2) ?
C4 C6 . 1.499(2) ?
C5 N1 . 1.346(2) yes
C5 H5 . 0.930 ?
C6 H61 . 0.960 ?
C6 H62 . 0.960 ?
C6 H63 . 0.960 ?
N1 O1 . 1.3165(17) yes
N2 O2 . 1.208(2) ?
N2 O3 . 1.216(2) ?
C7 C8 . 1.377(3) ?
C7 C9 . 1.390(2) ?
C7 H7 . 0.930 ?
C8 O4 . 1.375(2) yes
C8 C9 2_565 1.379(3) ?
C9 C8 2_565 1.379(3) ?
C9 H9 . 0.930 ?
C10 C12 2_656 1.379(2) ?
C10 C11 . 1.384(2) ?
C10 H10 . 0.930 ?
C11 O5 . 1.370(2) yes
C11 C12 . 1.385(2) ?
C12 C10 2_656 1.379(2) ?
C12 H12 . 0.930 ?
O4 HO4 . 0.82(3) yes
O5 HO5 . 0.83(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . -1.6(3) yes
C1 C2 C3 C4 . . 0.5(3) ?
C1 C2 C3 N2 . . -179.68(15) ?
C2 C3 C4 C5 . . 0.8(2) ?
N2 C3 C4 C5 . . -179.09(14) ?
C2 C3 C4 C6 . . -179.82(16) ?
N2 C3 C4 C6 . . 0.3(3) ?
C3 C4 C5 N1 . . -0.9(2) ?
C6 C4 C5 N1 . . 179.66(15) ?
C4 C5 N1 O1 . . -179.30(14) yes
C4 C5 N1 C1 . . -0.3(2) ?
C2 C1 N1 O1 . . -179.41(14) yes
C2 C1 N1 C5 . . 1.6(2) yes
C2 C3 N2 O2 . . 163.02(19) ?
C4 C3 N2 O2 . . -17.1(3) ?
C2 C3 N2 O3 . . -16.0(3) ?
C4 C3 N2 O3 . . 163.90(18) ?
C9 C7 C8 O4 . . -178.64(16) yes
C9 C7 C8 C9 . 2_565 -0.1(3) ?
C8 C7 C9 C8 . 2_565 0.1(3) ?
C12 C10 C11 O5 2_656 . 178.54(15) yes
C12 C10 C11 C12 2_656 . -0.2(3) ?
O5 C11 C12 C10 . 2_656 -178.61(15) yes
C10 C11 C12 C10 . 2_656 0.2(3) ?
