Electronic Supplementary Material for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2004

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_contact_author_name        'Alan Katritzky'
_publ_contact_author_address     
;
Department of Chemistry
University of Florida
PO Box 117200
Gainesville
FL
32611-7200
UNITED STATES OF AMERICA
;

_publ_contact_author_email       KATRITZKY@CHEM.UFL.EDU

_publ_section_title              
;
Preparation of Nitropyridines by Nitration of
Pyridines with Nitric Acid
;
loop_
_publ_author_name
'Alan Katritzky'
'Khalil A. Abboud'
'Novruz G. Akhedov'
'Rena G. Akhmedovaa'
'Alan Katritzky'
;
S.Majumdera
;
'G Senthil Murugan'
'Eric F.V. Scrivena'
'Anatoily V. Vakulenkoa'

data_ark1
_database_code_depnum_ccdc_archive 'CCDC 249216'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 N4 O6'
_chemical_formula_weight         242.16

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   'P 21/c'

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

_cell_length_a                   8.0407(8)
_cell_length_b                   11.7673(11)
_cell_length_c                   11.2852(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.476(2)
_cell_angle_gamma                90.00
_cell_volume                     1012.74(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    91
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, SHELXTL (Bruker 1998)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6137
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2287
_reflns_number_gt                1656
_computing_data_collection       'Bruker SMART (Bruker 1998)'
_computing_cell_refinement       'Bruker SMART & SAINT (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL (Bruker 2000)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0572P)^2^] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_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
O1 O 0.62328(16) 0.03644(10) 0.35751(10) 0.0547(3) Uani 1 1 d . . .
O2 O 0.86410(16) 0.12719(11) 0.37078(11) 0.0589(4) Uani 1 1 d . . .
O3 O 1.06420(13) 0.12218(9) 0.63306(12) 0.0523(3) Uani 1 1 d . . .
O4 O 0.94888(15) 0.29022(9) 0.60298(13) 0.0628(4) Uani 1 1 d . . .
O5 O 0.74331(16) -0.06263(9) 0.57939(12) 0.0550(3) Uani 1 1 d . . .
O6 O 0.78747(16) 0.05579(10) 0.73388(10) 0.0540(3) Uani 1 1 d . . .
N1 N 0.55592(15) 0.26746(10) 0.41884(10) 0.0339(3) Uani 1 1 d . . .
N2 N 0.75001(18) 0.09445(11) 0.41089(11) 0.0416(3) Uani 1 1 d . . .
N3 N 0.94191(15) 0.18817(10) 0.59889(12) 0.0381(3) Uani 1 1 d . . .
N4 N 0.76253(15) 0.03110(10) 0.62423(12) 0.0378(3) Uani 1 1 d . . .
C2 C 0.61029(16) 0.21722(11) 0.53012(11) 0.0269(3) Uani 1 1 d . . .
C3 C 0.54378(17) 0.24069(12) 0.62607(12) 0.0317(3) Uani 1 1 d . . .
H3A H 0.5886 0.2043 0.7050 0.038 Uiso 1 1 calc R . .
C4 C 0.40921(18) 0.31928(12) 0.60311(12) 0.0341(3) Uani 1 1 d . . .
H4A H 0.3589 0.3365 0.6667 0.041 Uiso 1 1 calc R . .
C5 C 0.34757(17) 0.37271(11) 0.48889(12) 0.0304(3) Uani 1 1 d . . .
C6 C 0.42750(19) 0.34361(12) 0.40015(13) 0.0358(3) Uani 1 1 d . . .
H6A H 0.3879 0.3804 0.3212 0.043 Uiso 1 1 calc R . .
C7 C 0.75862(18) 0.13469(11) 0.54159(12) 0.0304(3) Uani 1 1 d . . .
C8 C 0.2007(2) 0.45755(14) 0.45827(15) 0.0449(4) Uani 1 1 d . . .
H8A H 0.0882 0.4174 0.4359 0.067 Uiso 1 1 calc R . .
H8B H 0.2054 0.5046 0.3878 0.067 Uiso 1 1 calc R . .
H8C H 0.2127 0.5060 0.5311 0.067 Uiso 1 1 calc R . .

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
O1 0.0551(7) 0.0544(7) 0.0448(7) -0.0178(6) 0.0019(5) 0.0139(6)
O2 0.0597(8) 0.0772(9) 0.0526(7) 0.0092(6) 0.0359(6) 0.0239(6)
O3 0.0317(6) 0.0461(7) 0.0718(8) 0.0045(6) 0.0058(5) 0.0106(5)
O4 0.0411(7) 0.0322(7) 0.1137(12) 0.0002(6) 0.0227(7) -0.0001(5)
O5 0.0629(8) 0.0301(6) 0.0741(8) 0.0009(6) 0.0246(6) -0.0016(5)
O6 0.0663(8) 0.0563(7) 0.0362(6) 0.0162(5) 0.0117(5) 0.0132(6)
N1 0.0386(7) 0.0409(7) 0.0249(6) 0.0058(5) 0.0141(5) 0.0128(5)
N2 0.0469(8) 0.0425(7) 0.0366(7) -0.0006(6) 0.0147(6) 0.0202(6)
N3 0.0312(7) 0.0357(7) 0.0478(8) 0.0032(6) 0.0133(5) 0.0041(5)
N4 0.0320(7) 0.0371(7) 0.0432(8) 0.0090(6) 0.0104(5) 0.0061(5)
C2 0.0265(6) 0.0288(7) 0.0254(6) -0.0002(5) 0.0083(5) 0.0021(5)
C3 0.0346(7) 0.0392(8) 0.0227(6) 0.0030(6) 0.0111(5) 0.0032(6)
C4 0.0360(8) 0.0418(8) 0.0291(7) -0.0051(6) 0.0166(6) 0.0013(6)
C5 0.0275(7) 0.0319(7) 0.0320(7) -0.0041(5) 0.0096(5) 0.0018(5)
C6 0.0382(8) 0.0420(8) 0.0280(7) 0.0071(6) 0.0117(6) 0.0122(6)
C7 0.0318(7) 0.0305(7) 0.0291(7) 0.0009(6) 0.0099(6) 0.0033(5)
C8 0.0394(9) 0.0493(10) 0.0462(9) -0.0017(7) 0.0139(7) 0.0155(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
O1 N2 1.2158(17) . ?
O2 N2 1.2074(17) . ?
O3 N3 1.2157(15) . ?
O4 N3 1.2023(15) . ?
O5 N4 1.2029(15) . ?
O6 N4 1.2241(16) . ?
N1 C2 1.3303(16) . ?
N1 C6 1.3325(17) . ?
N2 C7 1.5296(17) . ?
N3 C7 1.5435(18) . ?
N4 C7 1.5291(17) . ?
C2 C3 1.3791(18) . ?
C2 C7 1.5114(18) . ?
C3 C4 1.3840(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3776(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3933(19) . ?
C5 C8 1.5004(19) . ?
C6 H6A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C2 N1 C6 117.04(11) . . ?
O2 N2 O1 127.61(13) . . ?
O2 N2 C7 117.07(13) . . ?
O1 N2 C7 115.23(12) . . ?
O4 N3 O3 127.05(12) . . ?
O4 N3 C7 116.74(11) . . ?
O3 N3 C7 116.19(12) . . ?
O5 N4 O6 126.94(13) . . ?
O5 N4 C7 119.95(12) . . ?
O6 N4 C7 113.11(12) . . ?
N1 C2 C3 123.99(12) . . ?
N1 C2 C7 112.38(11) . . ?
C3 C2 C7 123.59(12) . . ?
C2 C3 C4 117.48(12) . . ?
C2 C3 H3A 121.3 . . ?
C4 C3 H3A 121.3 . . ?
C5 C4 C3 120.55(12) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 116.70(12) . . ?
C4 C5 C8 122.86(12) . . ?
C6 C5 C8 120.44(13) . . ?
N1 C6 C5 124.22(12) . . ?
N1 C6 H6A 117.9 . . ?
C5 C6 H6A 117.9 . . ?
C2 C7 N4 115.32(11) . . ?
C2 C7 N2 108.84(10) . . ?
N4 C7 N2 109.10(11) . . ?
C2 C7 N3 113.37(11) . . ?
N4 C7 N3 103.72(10) . . ?
N2 C7 N3 106.00(10) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040