Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_section_title              
;A Competition Between N---O and C---O Through Space Interactions in
the Crystal Structures of 3,3'-Dinitro-2,2'-bipyridine N-Oxides and
N,N'-Dioxides
;
_publ_contact_author_name        'Prof. John Wallis'
_publ_contact_author_email       JOHN.WALLIS@NTU.AC.UK
loop_
_publ_author_name
J.Wallis
"Jane O'Leary"

# Attachment 'WALLIS_CIFS_B707822F.txt'

data_compound13
_database_code_depnum_ccdc_archive 'CCDC 648398'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3,3'-dinitro-2,2'-bipyridine-1-oxide
;
_chemical_name_common            3,3'-dinitro-2,2'-bipyridine-1-oxide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 N4 O5'
_chemical_formula_weight         262.19

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a

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'

_cell_length_a                   9.873(2)
_cell_length_b                   10.671(2)
_cell_length_c                   10.578(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.58(3)
_cell_angle_gamma                90.00
_cell_volume                     1078.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15743
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale green'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99
_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_special_details           
;
?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8399
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2430
_reflns_number_gt                1820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_cell_refinement       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction        
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2430
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0578(7) 0.0256(6) 0.0342(6) -0.0033(5) 0.0177(5) -0.0124(5)
O2A 0.0639(8) 0.0474(8) 0.0441(8) 0.0032(6) 0.0246(6) -0.0202(6)
O3A 0.0687(9) 0.0270(7) 0.0496(8) 0.0034(6) 0.0038(6) -0.0130(6)
N1A 0.0323(7) 0.0234(7) 0.0258(7) -0.0001(5) 0.0107(5) -0.0035(5)
N2A 0.0381(7) 0.0300(8) 0.0353(8) 0.0039(6) 0.0017(6) -0.0112(6)
C2A 0.0259(7) 0.0251(8) 0.0250(8) 0.0022(6) 0.0077(6) -0.0003(5)
C3A 0.0298(8) 0.0252(8) 0.0307(8) 0.0026(6) 0.0061(6) -0.0034(6)
C4A 0.0415(9) 0.0286(9) 0.0316(9) -0.0029(7) 0.0031(7) -0.0022(7)
C5A 0.0466(9) 0.0363(10) 0.0238(8) -0.0044(7) 0.0065(7) -0.0012(7)
C6A 0.0402(9) 0.0326(9) 0.0261(8) 0.0033(7) 0.0125(6) -0.0006(7)
O2B 0.0311(6) 0.0575(8) 0.0317(6) 0.0099(5) 0.0071(5) 0.0031(5)
O3B 0.0434(7) 0.0377(7) 0.0650(9) 0.0087(6) 0.0181(6) 0.0149(5)
N1B 0.0321(7) 0.0309(7) 0.0261(7) 0.0031(5) 0.0098(5) 0.0040(5)
N2B 0.0272(7) 0.0326(8) 0.0398(8) 0.0103(6) 0.0145(6) 0.0029(5)
C2B 0.0258(7) 0.0236(8) 0.0248(7) 0.0031(6) 0.0085(6) -0.0032(5)
C3B 0.0250(7) 0.0257(8) 0.0294(8) 0.0056(6) 0.0100(6) -0.0007(5)
C4B 0.0346(8) 0.0279(9) 0.0350(9) -0.0004(7) 0.0189(6) -0.0004(6)
C5B 0.0384(9) 0.0332(9) 0.0257(8) -0.0003(6) 0.0123(6) -0.0028(6)
C6B 0.0351(8) 0.0354(9) 0.0246(8) 0.0037(7) 0.0069(6) 0.0040(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_
_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) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055

data_compound14
_database_code_depnum_ccdc_archive 'CCDC 648399'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3,3-Dinitro-2,2-bipyridine-1,1-dioxide
;
_chemical_name_common            3,3-Dinitro-2,2-bipyridine-1,1-dioxide
_chemical_melting_point          475-479
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H6 N4 O6'
_chemical_formula_weight         278.19

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1226(3)
_cell_length_b                   7.4847(4)
_cell_length_c                   13.5200(8)
_cell_angle_alpha                102.8252(2)
_cell_angle_beta                 90.226(2)
_cell_angle_gamma                111.154(3)
_cell_volume                     560.99(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2075
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.986
_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_special_details           
;
PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.

Some additional spots are observed, indexing suggests a much larger cell,
a = 20.3578, b = c = 22.7139 Angstroms,
alpha = 89.5742, beta = 87.1617, gamma = 74.5216 degrees.
The refinement with the smaller cell provides a reasonable structural model
but with some elongations of the thermal ellipsoids.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6412
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1916
_reflns_number_gt                1279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_cell_refinement       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction        
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.4046P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1916
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
O1B O 0.2045(4) 0.3669(3) 0.35908(17) 0.0360(6) Uani 1 1 d . . .
O2A O -0.2708(4) 0.1602(4) 0.2426(2) 0.0581(8) Uani 1 1 d . . .
O3A O -0.3598(4) 0.2072(4) 0.3997(2) 0.0674(10) Uani 1 1 d . . .
N1B N 0.2392(4) 0.2908(3) 0.26718(19) 0.0279(6) Uani 1 1 d . . .
N2A N -0.2755(5) 0.1293(4) 0.3282(3) 0.0474(9) Uani 1 1 d . . .
C2A C 0.0143(5) -0.0305(4) 0.2981(2) 0.0290(7) Uani 1 1 d . . .
C3A C -0.1778(5) -0.0146(4) 0.3479(3) 0.0310(8) Uani 1 1 d . . .
C4A C -0.2873(6) -0.1319(4) 0.4117(3) 0.0351(8) Uani 1 1 d . . .
C5A C -0.2024(6) -0.2738(5) 0.4234(3) 0.0352(8) Uani 1 1 d . . .
C6A C -0.0124(6) -0.2912(4) 0.3756(3) 0.0401(9) Uani 1 1 d . . .
O1A O 0.2771(4) -0.1896(3) 0.2686(2) 0.0579(8) Uani 1 1 d . . .
O2B O -0.1217(5) -0.2876(4) 0.1082(2) 0.0727(10) Uani 1 1 d . . .
O3B O 0.1784(9) -0.2695(5) 0.0206(4) 0.164(3) Uani 1 1 d . . .
N1A N 0.0969(4) -0.1701(3) 0.3141(2) 0.0367(7) Uani 1 1 d . . .
N2B N 0.0734(7) -0.1979(5) 0.0834(3) 0.0833(14) Uani 1 1 d . . .
C2B C 0.1441(5) 0.0902(4) 0.2289(3) 0.0313(8) Uani 1 1 d . . .
C3B C 0.1835(6) 0.0160(5) 0.1296(3) 0.0491(10) Uani 1 1 d . . .
C4B C 0.3176(7) 0.1332(6) 0.0702(3) 0.0597(12) Uani 1 1 d . . .
C5B C 0.4085(6) 0.3353(5) 0.1124(3) 0.0443(9) Uani 1 1 d . . .
C6B C 0.3663(5) 0.4106(5) 0.2083(3) 0.0329(8) Uani 1 1 d . . .
H4A H -0.420(6) -0.118(5) 0.441(2) 0.042(9) Uiso 1 1 d . . .
H5A H -0.271(6) -0.355(5) 0.466(3) 0.046(10) Uiso 1 1 d . . .
H6A H 0.054(6) -0.391(6) 0.376(3) 0.055(10) Uiso 1 1 d . . .
H4B H 0.335(8) 0.075(6) 0.002(3) 0.079(14) Uiso 1 1 d . . .
H5B H 0.505(7) 0.424(6) 0.071(3) 0.059(11) Uiso 1 1 d . . .
H6B H 0.422(6) 0.548(5) 0.240(2) 0.042(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1B 0.0366(13) 0.0254(11) 0.0538(15) 0.0159(10) 0.0183(11) 0.0168(10)
O2A 0.0271(13) 0.0598(17) 0.113(2) 0.0636(17) 0.0231(14) 0.0204(12)
O3A 0.0512(16) 0.0384(15) 0.137(3) 0.0393(16) 0.0567(18) 0.0335(14)
N1B 0.0203(13) 0.0204(13) 0.0499(17) 0.0187(12) 0.0099(12) 0.0095(11)
N2A 0.0238(15) 0.0305(15) 0.105(3) 0.0363(17) 0.0332(17) 0.0178(13)
C2A 0.0215(16) 0.0178(15) 0.053(2) 0.0153(14) 0.0141(14) 0.0088(13)
C3A 0.0203(15) 0.0183(15) 0.060(2) 0.0171(15) 0.0161(15) 0.0096(13)
C4A 0.0271(17) 0.0243(16) 0.058(2) 0.0170(15) 0.0248(16) 0.0099(14)
C5A 0.0300(18) 0.0226(16) 0.055(2) 0.0212(16) 0.0113(16) 0.0052(14)
C6A 0.0274(17) 0.0209(17) 0.081(3) 0.0283(17) 0.0136(18) 0.0095(15)
O1A 0.0332(13) 0.0313(13) 0.128(2) 0.0386(14) 0.0484(15) 0.0225(11)
O2B 0.0697(19) 0.0402(15) 0.0646(18) 0.0030(13) 0.0385(15) -0.0251(14)
O3B 0.186(4) 0.0386(18) 0.195(4) -0.016(2) 0.166(4) -0.018(2)
N1A 0.0211(13) 0.0196(13) 0.078(2) 0.0219(13) 0.0224(14) 0.0116(11)
N2B 0.085(3) 0.0305(18) 0.094(3) -0.0016(18) 0.063(2) -0.0172(18)
C2B 0.0199(15) 0.0221(16) 0.056(2) 0.0162(14) 0.0157(14) 0.0079(13)
C3B 0.040(2) 0.0248(18) 0.067(3) 0.0102(17) 0.0272(19) -0.0059(16)
C4B 0.053(2) 0.042(2) 0.057(3) 0.010(2) 0.027(2) -0.0135(19)
C5B 0.0304(19) 0.039(2) 0.055(2) 0.0251(18) 0.0094(17) -0.0053(16)
C6B 0.0213(16) 0.0256(18) 0.056(2) 0.0234(17) 0.0069(15) 0.0048(14)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1B N1B 1.299(3) . ?
O3A N2A 1.229(4) . ?
O2A N2A 1.228(4) . ?
N1B C6B 1.364(4) . ?
N1B C2B 1.372(4) . ?
N2A C3A 1.476(4) . ?
C2A N1A 1.370(4) . ?
C2A C3A 1.386(4) . ?
C2A C2B 1.479(4) . ?
C3A C4A 1.371(4) . ?
C4A C5A 1.376(4) . ?
C5A C6A 1.365(4) . ?
C6A N1A 1.364(4) . ?
O1A N1A 1.304(3) . ?
O2B N2B 1.230(4) . ?
O3B N2B 1.214(4) . ?
N2B C3B 1.477(5) . ?
C2B C3B 1.392(5) . ?
C3B C4B 1.373(5) . ?
C4B C5B 1.390(5) . ?
C5B C6B 1.359(5) . ?

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
O1B N1B C6B 120.0(2) . . ?
O1B N1B C2B 119.9(2) . . ?
C6B N1B C2B 120.1(3) . . ?
O3A N2A O2A 124.9(3) . . ?
O2A N2A C3A 118.5(3) . . ?
O3A N2A C3A 116.6(3) . . ?
N1A C2A C3A 117.9(3) . . ?
N1A C2A C2B 115.4(2) . . ?
C3A C2A C2B 126.7(2) . . ?
C4A C3A C2A 122.9(3) . . ?
C4A C3A N2A 118.3(3) . . ?
C2A C3A N2A 118.7(3) . . ?
C3A C4A C5A 117.2(3) . . ?
C6A C5A C4A 120.8(3) . . ?
N1A C6A C5A 121.0(3) . . ?
O1A N1A C6A 120.2(2) . . ?
O1A N1A C2A 119.7(2) . . ?
C6A N1A C2A 120.1(2) . . ?
O3B N2B O2B 125.1(3) . . ?
O3B N2B C3B 117.2(3) . . ?
O2B N2B C3B 117.6(3) . . ?
N1B C2B C3B 117.7(3) . . ?
N1B C2B C2A 117.0(3) . . ?
C3B C2B C2A 125.2(3) . . ?
C4B C3B C2B 123.1(3) . . ?
C4B C3B N2B 117.3(3) . . ?
C2B C3B N2B 119.5(3) . . ?
C3B C4B C5B 116.8(4) . . ?
C6B C5B C4B 120.8(3) . . ?
C5B C6B N1B 121.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.065

data_compound15
_database_code_depnum_ccdc_archive 'CCDC 648400'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,5'-dimethyl-2,2'-bipyridine-1-oxide
;
_chemical_name_common            5,5'-dimethyl-2,2'-bipyridine-1-oxide
_chemical_melting_point          484-487
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4 O5'
_chemical_formula_weight         290.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a

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'

_cell_length_a                   8.1670(3)
_cell_length_b                   13.4699(6)
_cell_length_c                   11.3597(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7505(16)
_cell_angle_gamma                90.00
_cell_volume                     1245.37(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5802
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  1.000
_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_special_details           
;
PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data,
the entire data set is used to refine the cell, which is indexed from all
observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9531
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2826
_reflns_number_gt                1949
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_cell_refinement       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction        
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
There is a small degree of disorder in which pyridine N atom carries the
O atom: 92:8. The two N-O bonds were restrained to be similar.

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1002P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2826
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001

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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0595(11) 0.0170(9) 0.0339(10) 0.0048(7) -0.0142(8) -0.0030(7)
O2A 0.0406(8) 0.0355(9) 0.0183(8) 0.0009(6) -0.0022(6) 0.0076(6)
O3A 0.0323(8) 0.0250(8) 0.0355(9) 0.0017(6) 0.0040(6) 0.0077(6)
N1A 0.0343(9) 0.0209(10) 0.0229(9) 0.0034(7) -0.0065(7) -0.0043(7)
N2A 0.0192(7) 0.0232(9) 0.0226(9) 0.0012(7) -0.0006(6) 0.0000(7)
C2A 0.0199(9) 0.0260(11) 0.0176(9) 0.0014(8) -0.0025(7) -0.0004(8)
C3A 0.0180(8) 0.0236(11) 0.0180(9) 0.0017(7) 0.0007(7) 0.0012(7)
C4A 0.0232(9) 0.0204(11) 0.0232(10) -0.0020(8) 0.0013(7) -0.0023(8)
C5A 0.0253(9) 0.0307(12) 0.0181(10) -0.0014(8) -0.0001(7) -0.0005(8)
C6A 0.0316(10) 0.0280(12) 0.0206(10) 0.0046(9) -0.0059(8) 0.0003(9)
C7A 0.0410(12) 0.0387(14) 0.0230(11) -0.0016(9) -0.0094(9) -0.0043(10)
O2B 0.0220(7) 0.0298(9) 0.0427(9) 0.0003(6) -0.0046(6) -0.0047(6)
O3B 0.0301(8) 0.0337(9) 0.0544(11) -0.0175(8) -0.0030(7) 0.0054(6)
N1B 0.0231(8) 0.0343(11) 0.0242(9) -0.0011(7) -0.0027(6) 0.0002(7)
N2B 0.0223(8) 0.0268(10) 0.0251(9) -0.0011(7) -0.0032(6) 0.0008(7)
C2B 0.0229(9) 0.0224(11) 0.0190(10) 0.0028(8) -0.0015(7) -0.0034(8)
C3B 0.0201(9) 0.0233(10) 0.0197(10) 0.0038(8) -0.0019(7) -0.0007(7)
C4B 0.0255(10) 0.0226(11) 0.0206(10) -0.0001(8) -0.0010(7) -0.0012(8)
C5B 0.0251(9) 0.0273(11) 0.0174(10) 0.0055(8) -0.0024(7) -0.0043(8)
C6B 0.0211(10) 0.0327(12) 0.0271(11) -0.0013(9) -0.0019(7) -0.0013(8)
C7B 0.0263(9) 0.0308(12) 0.0250(11) 0.0029(9) -0.0066(8) -0.0059(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) . ?

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) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.061

data_compound16
_database_code_depnum_ccdc_archive 'CCDC 648401'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,5-Dimethyl-3,3-dinitro-2,2-bipyridine-1,1-dioxide
;
_chemical_name_common            
5,5-Dimethyl-3,3-dinitro-2,2-bipyridine-1,1-dioxide
_chemical_melting_point          484
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4 O6'
_chemical_formula_weight         306.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'

_cell_length_a                   12.044(4)
_cell_length_b                   7.544(3)
_cell_length_c                   15.093(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.480(3)
_cell_angle_gamma                90.00
_cell_volume                     1300.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5599
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.995
_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_special_details           ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6827
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1462
_reflns_number_gt                1272
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_cell_refinement       
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction        
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+3.1650P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1462
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002

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 0.04758(12) 0.0976(2) 0.62248(11) 0.0264(4) Uani 1 1 d . . .
O2A O -0.08876(13) -0.2845(2) 0.84069(12) 0.0333(5) Uani 1 1 d . . .
O3A O -0.26372(14) -0.1776(2) 0.81131(12) 0.0332(4) Uani 1 1 d . . .
N1A N -0.04995(14) 0.0313(2) 0.62782(12) 0.0197(4) Uani 1 1 d . . .
N2A N -0.17163(15) -0.1956(2) 0.79451(13) 0.0244(4) Uani 1 1 d . . .
C2A C -0.05463(16) -0.0412(3) 0.70990(14) 0.0196(5) Uani 1 1 d . . .
C3A C -0.16225(17) -0.1085(3) 0.71005(15) 0.0208(5) Uani 1 1 d . . .
C4A C -0.26190(17) -0.1042(3) 0.63352(15) 0.0219(5) Uani 1 1 d . . .
C5A C -0.25362(17) -0.0306(3) 0.55073(15) 0.0207(5) Uani 1 1 d . . .
C6A C -0.14710(18) 0.0334(3) 0.55020(15) 0.0215(5) Uani 1 1 d . . .
C7A C -0.35920(18) -0.0233(3) 0.46493(15) 0.0261(5) Uani 1 1 d . . .
H71 H -0.4058 0.0818 0.4677 0.039 Uiso 1 1 calc R . .
H72 H -0.4067 -0.1300 0.4618 0.039 Uiso 1 1 calc R . .
H73 H -0.3340 -0.0169 0.4093 0.039 Uiso 1 1 calc R . .
H4A H -0.336(2) -0.161(4) 0.6378(18) 0.027(6) Uiso 1 1 d . . .
H6A H -0.132(2) 0.078(4) 0.4998(19) 0.026(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0201(7) 0.0328(9) 0.0285(8) 0.0002(7) 0.0109(6) -0.0081(6)
O2A 0.0250(8) 0.0327(9) 0.0383(10) 0.0154(7) 0.0047(7) -0.0008(7)
O3A 0.0271(8) 0.0426(10) 0.0350(9) 0.0066(8) 0.0171(7) -0.0005(7)
N1A 0.0180(8) 0.0215(9) 0.0213(9) -0.0010(7) 0.0085(7) -0.0023(6)
N2A 0.0211(8) 0.0256(9) 0.0270(10) 0.0031(7) 0.0083(7) -0.0038(7)
C2A 0.0179(10) 0.0191(10) 0.0228(10) -0.0008(7) 0.0081(8) 0.0007(7)
C3A 0.0210(9) 0.0174(10) 0.0258(11) 0.0012(8) 0.0102(8) 0.0012(8)
C4A 0.0180(9) 0.0191(10) 0.0297(11) -0.0020(8) 0.0094(8) -0.0002(8)
C5A 0.0191(10) 0.0186(10) 0.0243(11) -0.0049(8) 0.0068(8) 0.0005(8)
C6A 0.0228(10) 0.0225(10) 0.0199(10) -0.0007(8) 0.0080(8) -0.0003(8)
C7A 0.0211(10) 0.0309(12) 0.0239(11) -0.0021(9) 0.0038(8) -0.0014(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 1.302(2) . ?
O2A N2A 1.221(2) . ?
O3A N2A 1.221(2) . ?
N1A C6A 1.369(3) . ?
N1A C2A 1.372(3) . ?
N2A C3A 1.470(3) . ?
C2A C3A 1.393(3) . ?
C2A C2A 1.479(4) 6_557 ?
C3A C4A 1.377(3) . ?
C4A C5A 1.399(3) . ?
C5A C6A 1.373(3) . ?
C5A C7A 1.501(3) . ?

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 119.06(17) . . ?
O1A N1A C2A 120.34(16) . . ?
C6A N1A C2A 120.60(17) . . ?
O2A N2A O3A 125.06(19) . . ?
O2A N2A C3A 117.83(17) . . ?
O3A N2A C3A 117.06(17) . . ?
N1A C2A C3A 116.85(18) . . ?
N1A C2A C2A 117.3(2) . 6_557 ?
C3A C2A C2A 125.9(2) . 6_557 ?
C4A C3A C2A 123.6(2) . . ?
C4A C3A N2A 116.87(18) . . ?
C2A C3A N2A 119.45(18) . . ?
C3A C4A C5A 117.94(18) . . ?
C6A C5A C4A 118.41(19) . . ?
C6A C5A C7A 121.30(19) . . ?
C4A C5A C7A 120.28(19) . . ?
N1A C6A C5A 122.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.069

data_compound22
_database_code_depnum_ccdc_archive 'CCDC 648402'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
8-nitroquinoline-1-oxide
;
_chemical_name_common            8-nitroquinoline-1-oxide
_chemical_melting_point          451-452
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 N2 O3'
_chemical_formula_weight         190.16

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8557(6)
_cell_length_b                   8.8130(6)
_cell_length_c                   11.4793(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.780(4)
_cell_angle_gamma                90.00
_cell_volume                     793.01(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1810
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8940
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         27.51
_reflns_number_total             1809
_reflns_number_gt                1465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.2631P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1809
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.19743(15) 0.06546(13) 0.10487(10) 0.0224(3) Uani 1 1 d . . .
O1 O 0.19433(14) 0.18531(12) 0.17087(10) 0.0316(3) Uani 1 1 d . . .
C7 C 0.42417(18) 0.21885(17) -0.14201(13) 0.0245(3) Uani 1 1 d . . .
N2 N 0.32942(16) 0.35577(13) 0.02402(11) 0.0260(3) Uani 1 1 d . . .
O3 O 0.45314(14) 0.39275(13) 0.08876(9) 0.0316(3) Uani 1 1 d . . .
C10 C 0.28222(18) -0.05649(15) -0.07175(12) 0.0212(3) Uani 1 1 d . . .
C9 C 0.27119(17) 0.07510(15) -0.00190(12) 0.0201(3) Uani 1 1 d . . .
O2 O 0.20265(15) 0.43317(12) 0.00243(12) 0.0387(3) Uani 1 1 d . . .
C8 C 0.34136(18) 0.21170(15) -0.04093(13) 0.0218(3) Uani 1 1 d . . .
C2 C 0.13510(19) -0.06767(16) 0.13992(14) 0.0254(3) Uani 1 1 d . . .
C4 C 0.21338(19) -0.19457(16) -0.03294(14) 0.0250(3) Uani 1 1 d . . .
C3 C 0.14116(19) -0.19832(16) 0.07168(14) 0.0258(3) Uani 1 1 d . . .
C6 C 0.43723(19) 0.08736(17) -0.21045(13) 0.0256(3) Uani 1 1 d . . .
C5 C 0.36659(19) -0.04569(17) -0.17692(13) 0.0241(3) Uani 1 1 d . . .
H5 H 0.373(2) -0.135(2) -0.2223(16) 0.033(5) Uiso 1 1 d . . .
H6 H 0.501(2) 0.0952(19) -0.2833(16) 0.030(4) Uiso 1 1 d . . .
H7 H 0.476(2) 0.314(2) -0.1623(15) 0.028(4) Uiso 1 1 d . . .
H4 H 0.221(2) -0.286(2) -0.0797(15) 0.030(4) Uiso 1 1 d . . .
H3 H 0.095(2) -0.291(2) 0.1000(16) 0.035(5) Uiso 1 1 d . . .
H2 H 0.090(2) -0.0682(18) 0.2172(15) 0.026(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0242(6) 0.0180(6) 0.0256(7) -0.0016(5) 0.0054(5) 0.0008(5)
O1 0.0421(7) 0.0216(5) 0.0325(6) -0.0076(4) 0.0130(5) -0.0015(5)
C7 0.0251(7) 0.0216(7) 0.0269(8) 0.0044(6) 0.0019(6) -0.0001(6)
N2 0.0319(7) 0.0157(6) 0.0310(7) 0.0010(5) 0.0065(5) -0.0020(5)
O3 0.0371(6) 0.0275(6) 0.0306(6) -0.0066(4) 0.0050(5) -0.0074(5)
C10 0.0205(7) 0.0179(7) 0.0249(7) -0.0007(5) -0.0008(5) 0.0018(5)
C9 0.0202(7) 0.0179(7) 0.0223(7) 0.0015(5) 0.0012(5) 0.0012(5)
O2 0.0394(7) 0.0198(6) 0.0571(8) -0.0013(5) 0.0049(6) 0.0081(5)
C8 0.0235(7) 0.0156(7) 0.0262(7) -0.0009(5) -0.0001(5) 0.0012(5)
C2 0.0256(7) 0.0239(7) 0.0274(8) 0.0034(6) 0.0065(6) -0.0008(6)
C4 0.0261(7) 0.0180(7) 0.0307(8) -0.0014(6) -0.0006(6) -0.0006(6)
C3 0.0251(7) 0.0186(7) 0.0339(8) 0.0036(6) 0.0020(6) -0.0021(6)
C6 0.0264(7) 0.0280(7) 0.0224(7) 0.0017(6) 0.0024(6) 0.0030(6)
C5 0.0257(7) 0.0236(7) 0.0227(7) -0.0027(6) 0.0006(6) 0.0024(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 O1 1.3010(15) . ?
N1 C2 1.3432(18) . ?
N1 C9 1.3924(18) . ?
C7 C8 1.369(2) . ?
C7 C6 1.408(2) . ?
N2 O2 1.2190(17) . ?
N2 O3 1.2280(16) . ?
N2 C8 1.4785(17) . ?
C10 C4 1.415(2) . ?
C10 C9 1.4158(19) . ?
C10 C5 1.418(2) . ?
C9 C8 1.4094(19) . ?
C2 C3 1.395(2) . ?
C4 C3 1.362(2) . ?
C6 C5 1.363(2) . ?

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
O1 N1 C2 120.89(12) . . ?
O1 N1 C9 119.21(11) . . ?
C2 N1 C9 119.87(12) . . ?
C8 C7 C6 119.44(13) . . ?
O2 N2 O3 125.31(13) . . ?
O2 N2 C8 117.14(12) . . ?
O3 N2 C8 117.33(12) . . ?
C4 C10 C9 119.14(13) . . ?
C4 C10 C5 122.36(13) . . ?
C9 C10 C5 118.47(12) . . ?
N1 C9 C8 121.75(12) . . ?
N1 C9 C10 119.54(12) . . ?
C8 C9 C10 118.67(13) . . ?
C7 C8 C9 121.78(13) . . ?
C7 C8 N2 115.95(12) . . ?
C9 C8 N2 122.28(12) . . ?
N1 C2 C3 121.74(14) . . ?
C3 C4 C10 119.24(13) . . ?
C4 C3 C2 120.44(13) . . ?
C5 C6 C7 120.30(14) . . ?
C6 C5 C10 121.31(13) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.054


