data_2008418
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  661
_journal_page_last  663
_publ_section_title
;
Methyl 1,4,5,6-tetrahydro-2-methyl-4-(2-nitrophenyl)-6-oxopyridine-3-
carboxylate
;
loop_
_publ_author_name
  'Viktor Kettmann'
  "J\'an Svetl\'ik"
_chemical_formula_moiety  'C14 H14 N2 O5'
_chemical_formula_sum  'C14 H14 N2 O5'
_chemical_formula_weight  290.27
_chemical_melting_point  479
_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  7.328(8)
_cell_length_b  8.729(9)
_cell_length_c  11.513(11)
_cell_angle_alpha  95.83(7)
_cell_angle_beta  107.27(8)
_cell_angle_gamma  97.34(7)
_cell_volume  689.9(13)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.395
_exptl_crystal_density_meas  1.400(10)
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.060
_refine_ls_wR_factor_obs  0.123
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  N1 1.0124(3) 0.4702(3) 0.1617(2) 0.0457(6) Uani d . 1 . N
  C2 0.8212(4) 0.4434(3) 0.1019(3) 0.0406(6) Uani d . 1 . C
  O1 0.7579(3) 0.4537(2) -0.0062(2) 0.0520(5) Uani d . 1 . O
  C3 0.6977(4) 0.4077(3) 0.1794(3) 0.0426(7) Uani d . 1 . C
  C4 0.7795(3) 0.3007(3) 0.2707(2) 0.0390(6) Uani d . 1 . C
  C5 0.9890(4) 0.3645(3) 0.3373(2) 0.0394(6) Uani d . 1 . C
  C6 1.0955(4) 0.4487(3) 0.2831(2) 0.0424(7) Uani d . 1 . C
  C7 0.7480(4) 0.1347(3) 0.2089(2) 0.0423(6) Uani d . 1 . C
  C8 0.5863(4) 0.0255(4) 0.1933(3) 0.0555(8) Uani d . 1 . C
  C9 0.5619(5) -0.1251(4) 0.1364(4) 0.0747(11) Uani d . 1 . C
  C10 0.7001(7) -0.1699(4) 0.0919(3) 0.0763(12) Uani d . 1 . C
  C11 0.8614(6) -0.0671(4) 0.1049(3) 0.0675(10) Uani d . 1 . C
  C12 0.8856(4) 0.0819(3) 0.1638(3) 0.0524(8) Uani d . 1 . C
  C13 1.0708(4) 0.3303(3) 0.4612(3) 0.0447(7) Uani d . 1 . C
  O2 1.2216(3) 0.3907(3) 0.5351(2) 0.0675(7) Uani d . 1 . O
  O3 0.9516(3) 0.2188(2) 0.4855(2) 0.0579(6) Uani d . 1 . O
  C14 1.0140(6) 0.1712(4) 0.6037(3) 0.0716(10) Uani d . 1 . C
  C15 1.3013(4) 0.5207(4) 0.3339(3) 0.0578(8) Uani d . 1 . C
  N2 0.4300(4) 0.0641(4) 0.2391(4) 0.0853(10) Uani d . 1 . N
  O4 0.3511(6) -0.0340(5) 0.2805(5) 0.185(2) Uani d . 1 . O
  O5 0.3805(4) 0.1871(4) 0.2279(3) 0.0934(9) Uani d . 1 . O
  H1 1.0959 0.5005 0.1200 0.055 Uiso d . 1 . H
  H3A 0.5626 0.3674 0.1276 0.052 Uiso d . 1 . H
  H3B 0.6937 0.5066 0.2255 0.052 Uiso d . 1 . H
  H4 0.7125 0.3081 0.3318 0.047 Uiso d . 1 . H
  H9 0.4541 -0.1907 0.1426 0.091 Uiso d . 1 . H
  H10 0.6789 -0.2699 0.0581 0.091 Uiso d . 1 . H
  H11 0.9577 -0.0975 0.0774 0.083 Uiso d . 1 . H
  H12 0.9974 0.1497 0.1719 0.064 Uiso d . 1 . H
  H14A 1.1419 0.1393 0.6056 0.086 Uiso d . 1 . H
  H14B 1.0285 0.2532 0.6674 0.086 Uiso d . 1 . H
  H14C 0.9261 0.0875 0.6077 0.086 Uiso d . 1 . H
  H15A 1.3645 0.5372 0.2757 0.071 Uiso d . 1 . H
  H15B 1.3726 0.4854 0.3968 0.071 Uiso d . 1 . H
  H15C 1.3126 0.6276 0.3754 0.071 Uiso d . 1 . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  N1 0.0392(12) 0.0557(15) 0.0441(14) 0.0025(10) 0.0163(11) 0.0131(11)
  C2 0.0424(15) 0.0361(14) 0.043(2) 0.0037(11) 0.0135(13) 0.0091(12)
  O1 0.0503(11) 0.0641(13) 0.0406(12) 0.0048(9) 0.0123(9) 0.0158(10)
  C3 0.0364(14) 0.048(2) 0.043(2) 0.0073(11) 0.0109(11) 0.0104(12)
  C4 0.0361(14) 0.044(2) 0.0372(14) 0.0056(11) 0.0115(11) 0.0073(12)
  C5 0.0369(14) 0.0401(15) 0.0386(15) 0.0066(11) 0.0086(11) 0.0043(11)
  C6 0.0398(14) 0.045(2) 0.039(2) 0.0042(12) 0.0100(12) 0.0024(12)
  C7 0.0422(14) 0.044(2) 0.0384(15) 0.0055(12) 0.0079(12) 0.0110(12)
  C8 0.045(2) 0.052(2) 0.064(2) 0.0026(13) 0.0074(15) 0.020(2)
  C9 0.071(2) 0.049(2) 0.082(3) -0.005(2) -0.006(2) 0.022(2)
  C10 0.102(3) 0.045(2) 0.057(2) 0.013(2) -0.013(2) 0.004(2)
  C11 0.096(3) 0.059(2) 0.050(2) 0.029(2) 0.019(2) 0.005(2)
  C12 0.061(2) 0.049(2) 0.047(2) 0.0095(14) 0.0171(15) 0.0060(14)
  C13 0.046(2) 0.050(2) 0.0370(15) 0.0108(13) 0.0117(13) 0.0041(13)
  O2 0.0532(13) 0.092(2) 0.0434(13) -0.0012(12) 0.0010(10) 0.0056(11)
  O3 0.0688(14) 0.0579(13) 0.0412(12) 0.0020(11) 0.0080(10) 0.0193(10)
  C14 0.098(3) 0.069(2) 0.047(2) 0.016(2) 0.016(2) 0.023(2)
  C15 0.041(2) 0.070(2) 0.055(2) -0.0046(14) 0.0109(14) 0.005(2)
  N2 0.056(2) 0.074(2) 0.128(3) -0.007(2) 0.035(2) 0.032(2)
  O4 0.144(3) 0.146(3) 0.343(7) 0.026(3) 0.162(4) 0.121(4)
  O5 0.065(2) 0.082(2) 0.141(3) 0.0068(14) 0.047(2) 0.014(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  N1 C2 . 1.343(4) yes
  N1 C6 . 1.392(4) yes
  C2 O1 . 1.209(4) yes
  C2 C3 . 1.475(4) n
  C3 C4 . 1.519(4) n
  C4 C5 . 1.500(4) n
  C4 C7 . 1.506(4) n
  C5 C6 . 1.332(4) n
  C5 C13 . 1.452(4) n
  C6 C15 . 1.473(4) ?
  C7 C12 . 1.371(4) ?
  C7 C8 . 1.377(4) ?
  C8 C9 . 1.372(5) ?
  C8 N2 . 1.458(5) yes
  C9 C10 . 1.346(6) ?
  C10 C11 . 1.349(5) ?
  C11 C12 . 1.369(5) ?
  C13 O2 . 1.194(4) yes
  C13 O3 . 1.331(4) yes
  O3 C14 . 1.423(4) ?
  N2 O5 . 1.184(4) yes
  N2 O4 . 1.189(4) yes