#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:52:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180360 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/29/7202980.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_7202980
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            'C12 H10 N4 O5'
_chemical_formula_weight         290.24
_chemical_melting_point          485.5(15)
_chemical_name_common            5,5'-dimethyl-2,2'-bipyridine-1-oxide
_chemical_name_systematic
;
5,5'-dimethyl-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7505(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1670(3)
_cell_length_b                   13.4699(6)
_cell_length_c                   11.3597(6)
_cell_measurement_reflns_used    5802
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1245.37(10)
_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      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9531
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.866
_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            green
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1002P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                1949
_reflns_number_total             2826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b707822f.txt
_cod_data_source_block           compound15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '484-487' was changed to '485.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7202980
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 0.1701(2) -0.07478(11) 0.42576(15) 0.0378(6) Uani 0.915(4) 1 d PD . .
O2A O 0.08437(17) 0.21841(11) 0.15771(12) 0.0317(4) Uani 1 1 d . . .
O3A O 0.02001(16) 0.32540(11) 0.28915(13) 0.0309(4) Uani 1 1 d . . .
N1A N 0.1934(2) 0.01925(12) 0.42965(14) 0.0265(4) Uani 1 1 d D . .
N2A N 0.07678(17) 0.24616(13) 0.26019(14) 0.0218(4) Uani 1 1 d . . .
C2A C 0.1228(2) 0.07865(15) 0.34304(16) 0.0214(4) Uani 1 1 d . . .
C3A C 0.1454(2) 0.17957(14) 0.35509(16) 0.0199(4) Uani 1 1 d . . .
C4A C 0.2369(2) 0.22256(16) 0.44921(17) 0.0223(4) Uani 1 1 d . . .
C5A C 0.3131(2) 0.15962(15) 0.53423(16) 0.0248(5) Uani 1 1 d . . .
C6A C 0.2887(2) 0.05928(16) 0.52163(18) 0.0272(5) Uani 1 1 d . . .
C7A C 0.4217(3) 0.19858(17) 0.63730(19) 0.0349(5) Uani 1 1 d . . .
H7A1 H 0.3633 0.1947 0.7091 0.052 Uiso 1 1 calc R . .
H7A2 H 0.4504 0.2679 0.6225 0.052 Uiso 1 1 calc R . .
H7A3 H 0.5221 0.1586 0.6474 0.052 Uiso 1 1 calc R . .
O1B O -0.190(2) 0.1231(11) 0.3135(13) 0.043(6) Uiso 0.085(4) 1 d PD . .
O2B O 0.33722(15) -0.01956(11) 0.21220(13) 0.0319(4) Uani 1 1 d . . .
O3B O 0.26067(17) -0.16413(12) 0.14712(14) 0.0398(4) Uani 1 1 d . . .
N1B N -0.14259(19) 0.06152(13) 0.24082(15) 0.0275(4) Uani 1 1 d D . .
N2B N 0.23118(18) -0.08027(13) 0.18045(14) 0.0250(4) Uani 1 1 d . . .
C2B C 0.0131(2) 0.02903(14) 0.24959(16) 0.0216(4) Uani 1 1 d . . .
C3B C 0.0583(2) -0.04938(14) 0.17968(16) 0.0212(4) Uani 1 1 d . . .
C4B C -0.0564(2) -0.09953(16) 0.10548(17) 0.0231(4) Uani 1 1 d . . .
C5B C -0.2189(2) -0.06781(15) 0.09876(16) 0.0235(4) Uani 1 1 d . . .
C6B C -0.2534(2) 0.01423(16) 0.16610(18) 0.0272(5) Uani 1 1 d . . .
C7B C -0.3514(2) -0.12101(16) 0.02373(18) 0.0278(5) Uani 1 1 d . . .
H7B1 H -0.4568 -0.0875 0.0303 0.042 Uiso 1 1 calc R . .
H7B2 H -0.3589 -0.1898 0.0508 0.042 Uiso 1 1 calc R . .
H7B3 H -0.3249 -0.1204 -0.0589 0.042 Uiso 1 1 calc R . .
H4A H 0.252(2) 0.2885(15) 0.4555(16) 0.012(5) Uiso 1 1 d . . .
H6A H 0.338(3) 0.0079(17) 0.575(2) 0.033(6) Uiso 1 1 d . . .
H4B H -0.026(2) -0.1492(17) 0.0634(19) 0.024(5) Uiso 1 1 d . . .
H6B H -0.366(3) 0.0405(15) 0.1624(18) 0.026(5) 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 C2A 120.30(16) . . ?
O1A N1A C6A 119.46(16) . . ?
C2A N1A C6A 120.25(17) . . ?
O3A N2A O2A 124.86(16) . . ?
O3A N2A C3A 117.68(15) . . ?
O2A N2A C3A 117.44(16) . . ?
N1A C2A C3A 117.65(17) . . ?
N1A C2A C2B 116.47(17) . . ?
C3A C2A C2B 125.56(16) . . ?
C2A C3A C4A 123.42(17) . . ?
C2A C3A N2A 119.17(16) . . ?
C4A C3A N2A 117.33(17) . . ?
C3A C4A C5A 117.65(19) . . ?
C6A C5A C4A 118.34(18) . . ?
C6A C5A C7A 119.75(18) . . ?
C4A C5A C7A 121.90(19) . . ?
N1A C6A C5A 122.61(18) . . ?
O1B N1B C2B 120.5(8) . . ?
O1B N1B C6B 120.1(8) . . ?
C2B N1B C6B 118.39(17) . . ?
O3B N2B O2B 123.81(15) . . ?
O3B N2B C3B 118.25(15) . . ?
O2B N2B C3B 117.92(16) . . ?
N1B C2B C3B 120.06(17) . . ?
N1B C2B C2A 114.65(16) . . ?
C3B C2B C2A 125.16(16) . . ?
C4B C3B C2B 121.39(16) . . ?
C4B C3B N2B 117.81(17) . . ?
C2B C3B N2B 120.78(15) . . ?
C3B C4B C5B 118.59(19) . . ?
C6B C5B C4B 116.84(17) . . ?
C6B C5B C7B 121.54(17) . . ?
C4B C5B C7B 121.60(18) . . ?
N1B C6B C5B 124.57(17) . . ?
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 1.281(2) . ?
O2A N2A 1.229(2) . ?
O3A N2A 1.220(2) . ?
N1A C2A 1.359(2) . ?
N1A C6A 1.362(3) . ?
N2A C3A 1.477(2) . ?
C2A C3A 1.377(3) . ?
C2A C2B 1.490(3) . ?
C3A C4A 1.380(3) . ?
C4A C5A 1.393(3) . ?
C5A C6A 1.372(3) . ?
C5A C7A 1.503(3) . ?
O1B N1B 1.253(7) . ?
O2B N2B 1.223(2) . ?
O3B N2B 1.222(2) . ?
N1B C2B 1.341(2) . ?
N1B C6B 1.348(2) . ?
N2B C3B 1.471(2) . ?
C2B C3B 1.390(3) . ?
C3B C4B 1.383(3) . ?
C4B C5B 1.390(3) . ?
C5B C6B 1.386(3) . ?
C5B C7B 1.503(2) . ?
