# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 188/272

data_global
 
_publ_contact_author_name           'Keith Orrell'
_publ_contact_author_address
;
Dr Keith Orrell
School of Chemistry
The University
Exeter
EX4 4QD
;

_publ_requested_journal             'Perkin Transactions 2'
_publ_section_title
;
Structures of 2-Nitrosopyridine and its 3- and 4-Methyl
Derivatives
;

 
data_s92
 
_audit_creation_date            2000-05-31T10:52:47-00:00
_audit_creation_method         'WinGX routine CIF_UPDATE'
 
_chemical_name_systematic
;
 ?
;
_chemical_formula_sum                   'C10 H8 N4 O2'
_chemical_formula_weight                216.2
 
 
_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                          6.231(2)
_cell_length_b                          8.198(3)
_cell_length_c                          10.300(4)
_cell_angle_alpha                       99.17(3)
_cell_angle_beta                        95.29(4)
_cell_angle_gamma                       106.630(16)
_cell_volume                            492.4(3)
_cell_formula_units_Z                   2
_cell_measurement_temperature           293(2)
 
 
_exptl_crystal_density_diffrn           1.458
_exptl_crystal_F_000                    224
_exptl_special_details
;
 ?
;
 
 
_exptl_absorpt_coefficient_mu           0.107
 
_diffrn_ambient_temperature             293(2)
_diffrn_radiation_wavelength            0.71069
_diffrn_radiation_type                  MoK\a
_diffrn_radiation_monochromator         graphite
_diffrn_measurement_device              'Enraf Nonius FAST TV area detector'
_diffrn_measurement_method              'phi and kappa scans'
_diffrn_standards_number                na
_diffrn_standards_interval_count        na
_diffrn_standards_interval_time         na
_diffrn_standards_decay_%               na
_diffrn_reflns_number                   2035
_diffrn_reflns_av_R_equivalents         0.2015
_diffrn_reflns_av_unetI/netI            0.1563
_diffrn_reflns_limit_h_min              -5
_diffrn_reflns_limit_h_max              6
_diffrn_reflns_limit_k_min              -9
_diffrn_reflns_limit_k_max              9
_diffrn_reflns_limit_l_min              -11
_diffrn_reflns_limit_l_max              11
_diffrn_reflns_theta_min                2.02
_diffrn_reflns_theta_max                25.03
_reflns_number_total                    1351
_reflns_number_gt                       887
_reflns_threshold_expression            >2sigma(I)
 
 
_computing_data_collection              MADNESS
_computing_cell_refinement              MADNESS
_computing_data_reduction               'MADNESS, ABSURD'
_computing_structure_solution           'SHELXS-96 (Sheldrick, 1990)'
_computing_structure_refinement         'SHELXL-96 (Sheldrick, 1996)'
 
 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  Weighted R-factors wR and all
 goodnesses 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 observed criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0399P)^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_extinction_method            none
_refine_ls_number_reflns                1351
_refine_ls_number_parameters            177
_refine_ls_number_restraints            0
_refine_ls_R_factor_all                 0.0781
_refine_ls_R_factor_gt                  0.0604
_refine_ls_wR_factor_gt                 0.1203
_refine_ls_wR_factor_all                0.126
_refine_ls_goodness_of_fit_gt           0.947
_refine_ls_goodness_of_fit_all          0.775
_refine_ls_restrained_S_all             0.775
_refine_ls_restrained_S_gt              0.947
_refine_ls_shift/su_max                 0.34
_refine_ls_shift/su_mean                0.003
_refine_diff_density_max                0.332
_refine_diff_density_min                -0.313
_refine_diff_density_rms                0.079
 
 
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
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_calc_flag
    _atom_site_refinement_flags
    _atom_site_disorder_group
N2 N 0.4160(4) 0.2169(4) 0.6712(3) 0.0166(7) Uani 1 d . .
O2 O 0.2751(4) 0.2718(3) 0.6072(2) 0.0223(7) Uani 1 d . .
N3 N 0.6071(5) 0.3319(4) 0.7351(3) 0.0198(8) Uani 1 d . .
N1 N 0.5565(4) -0.0210(4) 0.6632(3) 0.0171(8) Uani 1 d . .
O1 O 0.6521(4) 0.4880(3) 0.7224(3) 0.0325(8) Uani 1 d . .
N4 N 0.6354(5) 0.2129(4) 0.9256(3) 0.0201(8) Uani 1 d . .
C5 C 0.3749(6) 0.0320(4) 0.6580(3) 0.0148(9) Uani 1 d . .
C2 C 0.3036(6) -0.3103(5) 0.6240(4) 0.0197(9) Uani 1 d . .
C3 C 0.1190(6) -0.2502(5) 0.6152(4) 0.0213(9) Uani 1 d . .
C4 C 0.1544(6) -0.0727(5) 0.6343(4) 0.0184(9) Uani 1 d . .
C10 C 0.7654(7) 0.1767(5) 1.0225(4) 0.0269(10) Uani 1 d . .
C6 C 0.7456(6) 0.2871(4) 0.8388(4) 0.0180(9) Uani 1 d . .
C1 C 0.5157(6) -0.1924(5) 0.6469(3) 0.0184(9) Uani 1 d . .
C8 C 1.1028(7) 0.2989(5) 0.9403(4) 0.0288(11) Uani 1 d . .
C9 C 0.9954(6) 0.2174(5) 1.0323(4) 0.0278(10) Uani 1 d . .
C7 C 0.9759(6) 0.3373(5) 0.8380(4) 0.0243(10) Uani 1 d . .
H2 H 0.287(5) -0.423(4) 0.613(3) 0.000(8) Uiso 1 d . .
H3 H -0.033(6) -0.335(5) 0.607(3) 0.018(9) Uiso 1 d . .
H10 H 0.675(6) 0.131(5) 1.089(4) 0.030(12) Uiso 1 d . .
H9 H 1.081(7) 0.190(6) 1.113(4) 0.060(14) Uiso 1 d . .
H7 H 1.046(6) 0.399(5) 0.772(4) 0.022(10) Uiso 1 d . .
H8 H 1.252(7) 0.326(5) 0.953(4) 0.027(11) Uiso 1 d . .
H1 H 0.660(6) -0.230(5) 0.653(3) 0.029(10) Uiso 1 d . .
H4 H 0.034(6) -0.030(5) 0.630(4) 0.025(10) Uiso 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
N2 0.0094(16) 0.0217(18) 0.0208(17) 0.0050(14) -0.0023(13) 0.0092(13)
O2 0.0182(14) 0.0269(16) 0.0274(15) 0.0074(12) -0.0053(11) 0.0172(12)
N3 0.0117(17) 0.0197(19) 0.0289(19) 0.0066(15) -0.0027(13) 0.0070(13)
N1 0.0088(17) 0.0219(19) 0.0236(18) 0.0052(14) -0.0019(12) 0.0102(13)
O1 0.0289(16) 0.0166(16) 0.0494(19) 0.0108(13) -0.0091(13) 0.0049(12)
N4 0.0126(17) 0.0248(18) 0.0226(18) 0.0071(15) -0.0018(13) 0.0054(13)
C5 0.015(2) 0.016(2) 0.015(2) 0.0020(16) -0.0005(15) 0.0084(16)
C2 0.022(2) 0.016(2) 0.025(2) 0.0072(18) 0.0019(16) 0.0100(17)
C3 0.009(2) 0.024(2) 0.029(2) 0.0073(18) -0.0030(17) 0.0014(17)
C4 0.008(2) 0.026(2) 0.024(2) 0.0065(17) -0.0007(16) 0.0095(17)
C10 0.026(3) 0.028(2) 0.024(2) 0.0033(19) -0.0062(18) 0.0087(18)
C6 0.015(2) 0.016(2) 0.024(2) 0.0007(17) -0.0046(17) 0.0100(16)
C1 0.014(2) 0.024(2) 0.021(2) 0.0051(17) -0.0022(16) 0.0126(17)
C8 0.008(2) 0.036(3) 0.042(3) 0.000(2) -0.0052(19) 0.0127(19)
C9 0.021(2) 0.032(3) 0.027(2) -0.002(2) -0.0139(18) 0.0131(19)
C7 0.013(2) 0.029(2) 0.030(2) 0.004(2) 0.0006(17) 0.0077(17)
 
 
 
_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
N2 O2 1.274(3) . ?
N2 N3 1.325(4) . ?
N2 C5 1.444(4) . ?
N3 O1 1.260(4) . ?
N3 C6 1.468(4) . ?
N1 C5 1.323(4) . ?
N1 C1 1.334(5) . ?
N4 C6 1.299(4) . ?
N4 C10 1.351(5) . ?
C5 C4 1.371(5) . ?
C2 C1 1.370(5) . ?
C2 C3 1.376(5) . ?
C3 C4 1.387(5) . ?
C10 C9 1.365(5) . ?
C6 C7 1.376(5) . ?
C8 C9 1.362(6) . ?
C8 C7 1.389(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
O2 N2 N3 118.1(3) . . ?
O2 N2 C5 119.0(3) . . ?
N3 N2 C5 122.5(3) . . ?
O1 N3 N2 119.6(2) . . ?
O1 N3 C6 119.0(3) . . ?
N2 N3 C6 120.4(3) . . ?
C5 N1 C1 115.4(3) . . ?
C6 N4 C10 114.7(3) . . ?
N1 C5 C4 126.0(3) . . ?
N1 C5 N2 116.1(3) . . ?
C4 C5 N2 117.9(3) . . ?
C1 C2 C3 118.6(4) . . ?
C2 C3 C4 118.9(3) . . ?
C5 C4 C3 116.9(3) . . ?
N4 C10 C9 123.6(4) . . ?
N4 C6 C7 127.6(3) . . ?
N4 C6 N3 115.3(3) . . ?
C7 C6 N3 117.0(3) . . ?
N1 C1 C2 124.2(3) . . ?
C9 C8 C7 119.3(4) . . ?
C8 C9 C10 119.2(4) . . ?
C6 C7 C8 115.5(4) . . ?