#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/29/7202978.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202978
loop_
_publ_author_name
'O'Leary, Jane'
'Wallis, John D.'
_publ_section_title
;
 A competition between O⋯N and O⋯C through space
 interactions in the crystal structures of
 3,3′-dinitro-2,2′-bipyridine N-oxides and
 N,N′-dioxides
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              941
_journal_paper_doi               10.1039/b707822f
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C10 H6 N4 O5'
_chemical_formula_weight         262.19
_chemical_name_common            3,3'-dinitro-2,2'-bipyridine-1-oxide
_chemical_name_systematic
;
3,3'-dinitro-2,2'-bipyridine-1-oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.58(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.873(2)
_cell_length_b                   10.671(2)
_cell_length_c                   10.578(2)
_cell_measurement_reflns_used    15743
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     1078.6(4)
_computing_cell_refinement
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8399
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995)
See R.H. Blessing, Acta Cryst., (1995), A51, 33-38
;
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0784P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                1820
_reflns_number_total             2430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b707822f.txt
_cod_data_source_block           compound13
_cod_original_cell_volume        1078.5(4)
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7202978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.01209(12) 0.04964(10) 0.32894(10) 0.0381(3) Uani 1 1 d . . .
O2A O 0.20012(14) 0.42957(12) 0.17051(12) 0.0498(4) Uani 1 1 d . . .
O3A O 0.17610(14) 0.57008(11) 0.31024(12) 0.0504(4) Uani 1 1 d . . .
N1A N 0.04996(12) 0.16049(11) 0.37634(11) 0.0266(3) Uani 1 1 d . . .
N2A N 0.17115(14) 0.46173(13) 0.27105(13) 0.0358(3) Uani 1 1 d . . .
C2A C 0.08516(14) 0.24952(13) 0.29721(13) 0.0251(3) Uani 1 1 d . . .
C3A C 0.12931(15) 0.36484(14) 0.35242(15) 0.0288(4) Uani 1 1 d . . .
C4A C 0.13733(17) 0.39277(16) 0.48086(16) 0.0349(4) Uani 1 1 d . . .
C5A C 0.09815(18) 0.30035(16) 0.55589(16) 0.0360(4) Uani 1 1 d . . .
C6A C 0.05527(16) 0.18606(15) 0.50338(14) 0.0322(4) Uani 1 1 d . . .
O2B O 0.31126(11) 0.11713(12) 0.30610(11) 0.0402(3) Uani 1 1 d . . .
O3B O 0.30988(12) -0.02618(12) 0.16098(13) 0.0479(4) Uani 1 1 d . . .
N1B N -0.04755(12) 0.27067(12) 0.07786(11) 0.0293(3) Uani 1 1 d . . .
N2B N 0.26371(12) 0.06955(13) 0.19819(13) 0.0321(3) Uani 1 1 d . . .
C2B C 0.06295(14) 0.21516(13) 0.15711(13) 0.0243(3) Uani 1 1 d . . .
C3B C 0.14565(14) 0.13131(13) 0.10929(14) 0.0261(3) Uani 1 1 d . . .
C4B C 0.11717(16) 0.10426(15) -0.02201(15) 0.0307(4) Uani 1 1 d . . .
C5B C 0.00576(16) 0.16432(15) -0.10336(16) 0.0317(4) Uani 1 1 d . . .
C6B C -0.07348(17) 0.24556(15) -0.05000(15) 0.0318(4) Uani 1 1 d . . .
H4A H 0.1673(17) 0.4712(18) 0.5142(16) 0.041(5) Uiso 1 1 d . . .
H5A H 0.103(2) 0.3142(18) 0.643(2) 0.054(6) Uiso 1 1 d . . .
H6A H 0.0273(17) 0.1186(15) 0.5495(16) 0.033(4) Uiso 1 1 d . . .
H4B H 0.1690(18) 0.0437(16) -0.0523(16) 0.034(4) Uiso 1 1 d . . .
H5B H -0.0177(18) 0.1477(16) -0.1983(19) 0.044(5) Uiso 1 1 d . . .
H6B H -0.1527(17) 0.2894(15) -0.1045(15) 0.031(4) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A N1A C6A 119.93(12) . . ?
O1A N1A C2A 119.20(12) . . ?
C6A N1A C2A 120.87(13) . . ?
O2A N2A O3A 124.27(14) . . ?
O2A N2A C3A 118.40(14) . . ?
O3A N2A C3A 117.32(14) . . ?
N1A C2A C3A 117.43(13) . . ?
N1A C2A C2B 116.22(12) . . ?
C3A C2A C2B 126.21(13) . . ?
C4A C3A C2A 122.93(14) . . ?
C4A C3A N2A 118.16(14) . . ?
C2A C3A N2A 118.90(14) . . ?
C3A C4A C5A 117.31(16) . . ?
C6A C5A C4A 120.55(15) . . ?
N1A C6A C5A 120.89(14) . . ?
C2B N1B C6B 117.62(12) . . ?
O3B N2B O2B 123.88(13) . . ?
O3B N2B C3B 118.17(13) . . ?
O2B N2B C3B 117.95(13) . . ?
N1B C2B C3B 121.27(13) . . ?
N1B C2B C2A 114.09(12) . . ?
C3B C2B C2A 124.63(12) . . ?
C4B C3B C2B 120.85(13) . . ?
C4B C3B N2B 118.89(13) . . ?
C2B C3B N2B 120.26(13) . . ?
C5B C4B C3B 117.54(14) . . ?
C4B C5B C6B 118.96(15) . . ?
N1B C6B C5B 123.71(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A N1A 1.3023(16) . ?
O2A N2A 1.2181(17) . ?
O3A N2A 1.2251(17) . ?
N1A C6A 1.3592(19) . ?
N1A C2A 1.3677(19) . ?
N2A C3A 1.4695(19) . ?
C2A C3A 1.385(2) . ?
C2A C2B 1.488(2) . ?
C3A C4A 1.374(2) . ?
C4A C5A 1.381(2) . ?
C5A C6A 1.363(2) . ?
O2B N2B 1.2293(17) . ?
O3B N2B 1.2233(18) . ?
N1B C2B 1.3353(18) . ?
N1B C6B 1.339(2) . ?
N2B C3B 1.4578(19) . ?
C2B C3B 1.390(2) . ?
C3B C4B 1.377(2) . ?
C4B C5B 1.373(2) . ?
C5B C6B 1.380(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149138
