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
O'Leary, Jane; Wallis, John D.; CrystEngComm 9 (2007) 941–; doi:10.1039/b707822f

data_7202980
_publ_section_title
;
 A competition between O&#x22EF;N and O&#x22EF;C through space
 interactions in the crystal structures of
 3,3&#x2032;-dinitro-2,2&#x2032;-bipyridine N-oxides and
 N,N&#x2032;-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/[\s^2^(Fo^2^)+(0.1002P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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