#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017754.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_2017754
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Theodoro, Jahyr'
'Ellena, Javier'
'Montaño-A., Angela Marcela'
'Atencio, Reynaldo'
_publ_section_title
;
 3-Nitrophenol--4,4'-bipyridyl N,N'-dioxide (2/1): a DFT
 study and CSD analysis of DPNO molecular complexes
;
_journal_coeditor_code           GG3235
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o425
_journal_page_last               o428
_journal_paper_doi               10.1107/S0108270110024601
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C6 H5 N O3 , C10 H8 N2 O2'
_chemical_formula_moiety         '2(C6 H5 N O3), C10 H8 N2 O2'
_chemical_formula_sum            'C22 H18 N4 O8'
_chemical_formula_weight         466.4
_chemical_name_systematic
;
3-Nitrophenol--4,4'-bipyridyl N,N'-dioxide (2/1)
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.700(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5167(14)
_cell_length_b                   5.9729(13)
_cell_length_c                   18.2602(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291
_cell_measurement_theta_max      19.63
_cell_measurement_theta_min      17.24
_cell_volume                     1104.2(3)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_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 Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'PARST95 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'four-circle diffractometer'
_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  0.016
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2052
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  150
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.048
_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)+(0.0680P)²+0.1527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.130
_reflns_number_gt                1243
_reflns_number_total             1937
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3235.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017754
_cod_database_fobs_code          2017754
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_disorder_assembly
_atom_site_disorder_group
O O1 0.2358(2) 0.5744(3) 0.54388(11) 0.0776(6) Uani d . 1 . .
O O2 0.3763(3) 0.7214(5) 0.49546(15) 0.1268(11) Uani d . 1 . .
O O3 0.2511(2) 1.0219(3) 0.77541(10) 0.0646(5) Uani d . 1 . .
H H31 0.200(3) 0.888(6) 0.7740(17) 0.094(11) Uiso d . 1 . .
N N1 0.3180(2) 0.7149(4) 0.54378(11) 0.0616(6) Uani d . 1 . .
C C1 0.3452(2) 0.8859(4) 0.60354(12) 0.0485(6) Uani d . 1 . .
C C2 0.4253(3) 1.0641(5) 0.59824(15) 0.0654(8) Uani d . 1 . .
H H2 0.4648 1.0742 0.5585 0.078 Uiso calc R 1 . .
C C3 0.4449(3) 1.2270(5) 0.65351(15) 0.0681(8) Uani d . 1 . .
H H3 0.4987 1.3490 0.6513 0.082 Uiso calc R 1 . .
C C4 0.3861(3) 1.2114(4) 0.71190(14) 0.0576(7) Uani d . 1 . .
H H4 0.3998 1.3234 0.7486 0.069 Uiso calc R 1 . .
C C5 0.3067(2) 1.0306(4) 0.71658(13) 0.0481(6) Uani d . 1 . .
C C6 0.2857(2) 0.8647(4) 0.66170(12) 0.0468(6) Uani d . 1 . .
H H6 0.2327 0.7418 0.6641 0.056 Uiso calc R 1 . .
O O4 0.11874(19) 0.6496(3) 0.76650(8) 0.0649(6) Uani d . 1 . .
N N2 0.0858(2) 0.6079(3) 0.83024(10) 0.0488(5) Uani d . 1 . .
C C7 0.0090(3) 0.7510(4) 0.85444(13) 0.0529(6) Uani d . 1 . .
H H7 -0.0219 0.8791 0.8262 0.064 Uiso calc R 1 . .
C C8 -0.0249(2) 0.7109(4) 0.92079(12) 0.0508(6) Uani d . 1 . .
H H8 -0.0782 0.8133 0.9370 0.061 Uiso calc R 1 . .
C C9 0.0181(2) 0.5226(4) 0.96382(11) 0.0391(5) Uani d . 1 . .
C C10 0.0962(2) 0.3773(4) 0.93591(13) 0.0539(7) Uani d . 1 . .
H H10 0.1269 0.2467 0.9626 0.065 Uiso calc R 1 . .
C C11 0.1290(3) 0.4219(4) 0.86998(14) 0.0599(7) Uani d . 1 . .
H H11 0.1819 0.3219 0.8525 0.072 Uiso calc R 1 . .
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'
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'
Cl Cl 0.1484 0.1585 '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
0 1 3
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
C5 O3 H31 . . 111.7(18) ?
O2 N1 O1 . . 122.1(2) ?
O2 N1 C1 . . 119.2(2) ?
O1 N1 C1 . . 118.7(2) ?
C2 C1 C6 . . 122.7(2) ?
C2 C1 N1 . . 119.1(2) ?
C6 C1 N1 . . 118.2(2) ?
C3 C2 C1 . . 117.9(2) ?
C3 C2 H2 . . 121.0 ?
C1 C2 H2 . . 121.0 ?
C4 C3 C2 . . 120.8(3) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.5(2) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
O3 C5 C4 . . 118.4(2) ?
O3 C5 C6 . . 121.9(2) ?
C4 C5 C6 . . 119.7(2) ?
C1 C6 C5 . . 118.4(2) ?
C1 C6 H6 . . 120.8 ?
C5 C6 H6 . . 120.8 ?
O4 N2 C7 . . 119.8(2) ?
O4 N2 C11 . . 120.1(2) ?
C7 N2 C11 . . 120.05(19) ?
N2 C7 C8 . . 120.4(2) ?
N2 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C7 C8 C9 . . 121.5(2) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C8 C9 C10 . . 116.02(19) ?
C8 C9 C9 . 3_567 121.9(2) ?
C10 C9 C9 . 3_567 122.1(2) ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
N2 C11 C10 . . 120.7(2) ?
N2 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
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 . 1.205(3) ?
O2 N1 . 1.204(3) ?
O3 C5 . 1.356(3) ?
O3 H31 . 0.96(3) ?
N1 C1 . 1.465(3) ?
C1 C2 . 1.377(3) ?
C1 C6 . 1.377(3) ?
C2 C3 . 1.376(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C6 H6 . 0.9300 ?
O4 N2 . 1.325(2) ?
N2 C7 . 1.331(3) ?
N2 C11 . 1.337(3) ?
C7 C8 . 1.374(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.376(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.383(3) ?
C9 C9 3_567 1.496(4) ?
C10 C11 . 1.365(3) ?
C10 H10 . 0.9300 ?
C11 H11 . 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
O3 H31 O4 1 0.96(3) 1.65(3) 2.605(3) 175(3)
O3 H31 N2 1 0.96(3) 2.44(3) 3.329(3) 154(2)
C8 H8 O1 2_556 0.93 2.37 3.290(3) 170.1
C7 H7 O4 2_556 0.93 2.36 3.278(3) 167.8
C2 H2 O2 3_676 0.93 2.48 3.295(3) 146.4
C6 H6 O4 1 0.93 2.54 3.196(3) 127.9
C10 H10 O1 4_566 0.93 2.50 3.428(3) 172.3
C11 H11 O3 1_545 0.93 2.51 3.397(3) 160.7
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 N1 C1 C2 . . . . 7.4(4) ?
O1 N1 C1 C2 . . . . -171.2(2) ?
O2 N1 C1 C6 . . . . -174.7(3) ?
O1 N1 C1 C6 . . . . 6.7(4) ?
C6 C1 C2 C3 . . . . -0.4(4) ?
N1 C1 C2 C3 . . . . 177.4(2) ?
C1 C2 C3 C4 . . . . -0.1(4) ?
C2 C3 C4 C5 . . . . 0.5(4) ?
C3 C4 C5 O3 . . . . 179.7(2) ?
C3 C4 C5 C6 . . . . -0.4(4) ?
C2 C1 C6 C5 . . . . 0.5(4) ?
N1 C1 C6 C5 . . . . -177.3(2) ?
O3 C5 C6 C1 . . . . 179.8(2) ?
C4 C5 C6 C1 . . . . -0.1(3) ?
O4 N2 C7 C8 . . . . -179.4(2) ?
C11 N2 C7 C8 . . . . 0.9(4) ?
N2 C7 C8 C9 . . . . -0.4(4) ?
C7 C8 C9 C10 . . . . -0.4(4) ?
C7 C8 C9 C9 . . . 3_567 180.0(3) ?
C8 C9 C10 C11 . . . . 0.8(4) ?
C9 C9 C10 C11 3_567 . . . -179.6(3) ?
O4 N2 C11 C10 . . . . 179.8(2) ?
C7 N2 C11 C10 . . . . -0.6(4) ?
C9 C10 C11 N2 . . . . -0.3(4) ?
