#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202358.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2202358
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1347
_journal_page_last  o1348
_publ_section_title
;
Dimethyl 5-oxo-4,5-dihydro-1,2,3,4-tetrazole-1,4-dicarboxylate
;
loop_
_publ_author_name
  'Crockett, Rowena'
  'Forrester, Alexander R.'
  'Howie, R. Alan'
_chemical_formula_moiety  'C5 H6 N4 O5'
_chemical_formula_sum  'C5 H6 N4 O5'
_chemical_formula_iupac  'C5 H6 N4 O5'
_chemical_formula_weight  202.14
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  10.023(17)
_cell_length_b  15.92(3)
_cell_length_c  12.123(15)
_cell_angle_alpha  90.00
_cell_angle_beta  115.67(11)
_cell_angle_gamma  90.00
_cell_volume  1744(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.540
_diffrn_ambient_temperature  298(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  N1A 0.7832(7) 0.9408(5) 0.6776(6) 0.0612(18) Uani d . 1 . . N
  N2A 0.6546(9) 0.9887(6) 0.6248(8) 0.078(2) Uani d . 1 . . N
  N3A 0.5497(8) 0.9415(6) 0.5589(7) 0.074(2) Uani d . 1 . . N
  N4A 0.6056(7) 0.8618(5) 0.5654(6) 0.0603(18) Uani d . 1 . . N
  C5A 0.7574(9) 0.8570(6) 0.6440(8) 0.061(2) Uani d . 1 . . C
  O5A 0.8408(6) 0.7995(4) 0.6705(6) 0.0744(17) Uani d . 1 . . O
  C1A 0.9190(10) 0.9760(7) 0.7628(8) 0.068(2) Uani d . 1 . . C
  O1A 1.0264(7) 0.9336(5) 0.8164(6) 0.088(2) Uani d . 1 . . O
  O2A 0.9074(8) 1.0579(5) 0.7673(6) 0.086(2) Uani d . 1 . . O
  C2A 1.0365(13) 1.1007(9) 0.8518(12) 0.113(5) Uani d . 1 . . C
  H1A 1.0365 1.1019 0.9309 0.170 Uiso calc R 1 . . H
  H2A 1.0367 1.1571 0.8240 0.170 Uiso calc R 1 . . H
  H3A 1.1233 1.0718 0.8573 0.170 Uiso calc R 1 . . H
  C3A 0.5176(10) 0.7925(6) 0.5014(8) 0.063(2) Uani d . 1 . . C
  O3A 0.5691(8) 0.7251(5) 0.4989(7) 0.099(2) Uani d . 1 . . O
  O4A 0.3804(7) 0.8155(5) 0.4408(7) 0.083(2) Uani d . 1 . . O
  C4A 0.2790(10) 0.7521(7) 0.3664(9) 0.080(3) Uani d . 1 . . C
  H4A 0.3300 0.7138 0.3368 0.119 Uiso calc R 1 . . H
  H5A 0.1992 0.7782 0.2983 0.119 Uiso calc R 1 . . H
  H6A 0.2400 0.7219 0.4146 0.119 Uiso calc R 1 . . H
  N1B 0.0776(7) 0.2916(4) 0.5457(6) 0.0555(16) Uani d . 1 . . N
  N2B 0.0287(8) 0.2117(6) 0.5470(7) 0.066(2) Uani d . 1 . . N
  N3B 0.1341(8) 0.1651(5) 0.6183(7) 0.0616(17) Uani d . 1 . . N
  N4B 0.2579(7) 0.2169(4) 0.6682(6) 0.0497(15) Uani d . 1 . . N
  C5B 0.2250(9) 0.2980(6) 0.6242(7) 0.057(2) Uani d . 1 . . C
  O5B 0.3049(7) 0.3571(4) 0.6428(6) 0.0796(18) Uani d . 1 . . O
  C1B -0.0130(10) 0.3554(6) 0.4693(7) 0.063(2) Uani d . 1 . . C
  O1B 0.0323(8) 0.4233(5) 0.4687(6) 0.0846(19) Uani d . 1 . . O
  O2B -0.1487(7) 0.3266(5) 0.4095(6) 0.0798(19) Uani d . 1 . . O
  C2B -0.2541(11) 0.3915(9) 0.3325(10) 0.100(4) Uani d . 1 . . C
  H1B -0.2162 0.4462 0.3633 0.151 Uiso calc R 1 . . H
  H2B -0.3480 0.3837 0.3345 0.151 Uiso calc R 1 . . H
  H3B -0.2664 0.3864 0.2497 0.151 Uiso calc R 1 . . H
  C3B 0.3968(9) 0.1853(5) 0.7484(7) 0.0551(19) Uani d . 1 . . C
  O3B 0.5033(7) 0.2293(5) 0.7964(6) 0.087(2) Uani d . 1 . . O
  O4B 0.3894(7) 0.1054(4) 0.7646(6) 0.0811(19) Uani d . 1 . . O
  C4B 0.5287(13) 0.0650(9) 0.8429(11) 0.103(4) Uani d . 1 . . C
  H4B 0.6009 0.0769 0.8129 0.154 Uiso calc R 1 . . H
  H5B 0.5141 0.0054 0.8427 0.154 Uiso calc R 1 . . H
  H6B 0.5630 0.0860 0.9249 0.154 Uiso calc R 1 . . H
  N1C 0.0401(6) 0.4396(4) 0.8459(6) 0.0488(14) Uani d . 1 . . N
  N2C 0.0876(10) 0.4835(6) 0.9535(8) 0.083(2) Uani d . 1 . . N
  N3C 0.1773(9) 0.4487(7) 1.0399(7) 0.081(2) Uani d . 1 . . N
  N4C 0.1993(7) 0.3660(5) 0.9916(7) 0.0633(18) Uani d . 1 . . N
  C5C 0.1171(9) 0.3594(6) 0.8724(9) 0.060(2) Uani d . 1 . . C
  O5C 0.1068(8) 0.3059(4) 0.8059(6) 0.0764(17) Uani d . 1 . . O
  C1C -0.0599(11) 0.4690(7) 0.7335(10) 0.078(3) Uani d . 1 . . C
  O1C -0.1010(8) 0.4236(5) 0.6419(6) 0.095(2) Uani d . 1 . . O
  O2C -0.0997(7) 0.5406(5) 0.7437(9) 0.105(3) Uani d . 1 . . O
  C2C -0.2199(14) 0.5770(8) 0.6213(11) 0.106(4) Uani d . 1 . . C
  H1C -0.2147 0.5486 0.5534 0.159 Uiso calc R 1 . . H
  H2C -0.2025 0.6360 0.6167 0.159 Uiso calc R 1 . . H
  H3C -0.3162 0.5690 0.6185 0.159 Uiso calc R 1 . . H
  C3C 0.3038(10) 0.3144(6) 1.0802(10) 0.069(2) Uani d . 1 . . C
  O3C 0.3747(8) 0.3341(6) 1.1829(7) 0.102(3) Uani d . 1 . . O
  O4C 0.3064(7) 0.2431(5) 1.0261(7) 0.093(2) Uani d . 1 . . O
  C4C 0.4150(16) 0.1835(9) 1.1081(14) 0.145(6) Uani d . 1 . . C
  H4C 0.5130 0.2043 1.1297 0.217 Uiso calc R 1 . . H
  H5C 0.4028 0.1302 1.0677 0.217 Uiso calc R 1 . . H
  H6C 0.4005 0.1767 1.1809 0.217 Uiso calc R 1 . . H
  N1D 0.4752(7) 0.9605(5) 0.1618(6) 0.0606(18) Uani d . 1 . . N
  N2D 0.3769(10) 0.9618(6) 0.2161(9) 0.091(3) Uani d . 1 . . N
  N3D 0.2763(9) 0.9109(7) 0.1625(8) 0.090(3) Uani d . 1 . . N
  N4D 0.3025(7) 0.8716(5) 0.0696(7) 0.0665(19) Uani d . 1 . . N
  C5D 0.4309(9) 0.9005(6) 0.0688(7) 0.065(2) Uani d . 1 . . C
  O5D 0.4863(9) 0.8831(6) 0.0038(7) 0.099(2) Uani d . 1 . . O
  C1D 0.6122(9) 1.0038(5) 0.2161(8) 0.059(2) Uani d . 1 . . C
  O1D 0.6957(7) 1.0033(5) 0.1716(6) 0.089(2) Uani d . 1 . . O
  O2D 0.6190(7) 1.0424(4) 0.3135(7) 0.0860(19) Uani d . 1 . . O
  C2D 0.7561(14) 1.0860(8) 0.3869(12) 0.130(6) Uani d . 1 . . C
  H1D 0.8351 1.0459 0.4212 0.195 Uiso calc R 1 . . H
  H2D 0.7462 1.1159 0.4517 0.195 Uiso calc R 1 . . H
  H3D 0.7777 1.1249 0.3363 0.195 Uiso calc R 1 . . H
  C3D 0.1946(13) 0.8050(7) 0.0091(9) 0.079(3) Uani d . 1 . . C
  O3D 0.0990(9) 0.7898(6) 0.0335(9) 0.110(3) Uani d . 1 . . O
  O4D 0.2383(7) 0.7726(4) -0.0689(6) 0.0849(19) Uani d . 1 . . O
  C4D 0.1302(17) 0.7034(12) -0.1370(13) 0.144(6) Uani d . 1 . . C
  H4D 0.1270 0.6629 -0.0794 0.215 Uiso calc R 1 . . H
  H5D 0.1616 0.6763 -0.1925 0.215 Uiso calc R 1 . . H
  H6D 0.0334 0.7270 -0.1821 0.215 Uiso calc R 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
  N1A 0.052(4) 0.067(5) 0.068(4) 0.009(4) 0.029(3) 0.008(4)
  N2A 0.070(5) 0.073(5) 0.092(6) 0.026(4) 0.036(5) 0.020(5)
  N3A 0.057(4) 0.074(5) 0.074(5) 0.021(4) 0.014(4) -0.001(4)
  N4A 0.056(4) 0.068(5) 0.052(4) 0.015(4) 0.019(3) 0.011(3)
  C5A 0.062(5) 0.066(6) 0.062(5) 0.005(5) 0.034(4) 0.009(4)
  O5A 0.064(3) 0.057(3) 0.097(4) 0.027(3) 0.031(3) 0.015(3)
  C1A 0.063(5) 0.087(8) 0.059(5) 0.003(5) 0.032(4) 0.010(5)
  O1A 0.066(4) 0.096(6) 0.091(5) 0.022(4) 0.024(4) 0.011(4)
  O2A 0.083(5) 0.066(5) 0.093(5) -0.005(3) 0.023(4) 0.012(4)
  C2A 0.097(8) 0.105(9) 0.125(9) -0.042(8) 0.035(7) 0.023(8)
  C3A 0.067(5) 0.067(6) 0.049(4) 0.015(5) 0.020(4) 0.025(4)
  O3A 0.082(5) 0.067(5) 0.119(6) 0.023(4) 0.016(4) 0.016(4)
  O4A 0.061(4) 0.087(5) 0.103(5) 0.014(4) 0.037(4) 0.005(4)
  C4A 0.069(6) 0.085(7) 0.087(6) -0.008(5) 0.035(5) 0.003(6)
  N1B 0.055(4) 0.053(4) 0.060(4) -0.009(3) 0.027(3) -0.004(3)
  N2B 0.060(4) 0.079(5) 0.065(4) -0.018(4) 0.032(4) -0.009(4)
  N3B 0.055(4) 0.055(4) 0.077(4) -0.004(3) 0.030(4) 0.000(4)
  N4B 0.050(4) 0.043(4) 0.060(4) -0.010(3) 0.028(3) -0.010(3)
  C5B 0.062(5) 0.063(5) 0.051(4) -0.025(4) 0.027(4) -0.013(4)
  O5B 0.070(4) 0.068(4) 0.093(5) -0.018(4) 0.028(3) -0.012(4)
  C1B 0.071(5) 0.067(6) 0.053(5) -0.016(5) 0.029(4) -0.001(4)
  O1B 0.096(5) 0.079(5) 0.087(4) 0.004(4) 0.047(4) 0.002(4)
  O2B 0.067(4) 0.093(5) 0.073(4) 0.002(4) 0.024(3) -0.006(4)
  C2B 0.064(6) 0.133(11) 0.091(7) 0.029(7) 0.021(5) 0.025(7)
  C3B 0.055(5) 0.052(5) 0.061(5) -0.005(4) 0.028(4) -0.016(4)
  O3B 0.062(4) 0.089(5) 0.090(4) -0.015(4) 0.014(3) -0.020(4)
  O4B 0.070(4) 0.066(5) 0.095(4) 0.007(3) 0.025(4) 0.008(4)
  C4B 0.086(7) 0.102(9) 0.097(8) 0.012(6) 0.017(6) 0.010(7)
  N1C 0.047(3) 0.042(3) 0.056(4) 0.003(3) 0.020(3) -0.006(3)
  N2C 0.089(6) 0.090(6) 0.078(6) -0.005(5) 0.046(5) -0.003(5)
  N3C 0.075(5) 0.114(7) 0.051(4) -0.022(5) 0.024(4) -0.009(5)
  N4C 0.057(4) 0.058(4) 0.076(5) -0.004(4) 0.029(4) 0.003(4)
  C5C 0.053(4) 0.062(6) 0.070(6) -0.017(4) 0.030(4) 0.000(5)
  O5C 0.094(4) 0.061(4) 0.079(4) 0.005(3) 0.041(3) -0.007(4)
  C1C 0.076(6) 0.078(7) 0.091(7) -0.012(6) 0.046(6) 0.006(6)
  O1C 0.107(5) 0.098(5) 0.068(4) 0.014(4) 0.027(4) 0.001(4)
  O2C 0.067(4) 0.069(5) 0.176(8) 0.005(4) 0.049(5) 0.015(5)
  C2C 0.119(9) 0.082(8) 0.115(8) 0.034(7) 0.049(7) 0.055(7)
  C3C 0.059(5) 0.063(6) 0.086(7) -0.002(5) 0.032(5) 0.012(6)
  O3C 0.081(4) 0.145(8) 0.076(5) 0.010(5) 0.029(4) -0.001(5)
  O4C 0.074(4) 0.070(5) 0.106(5) 0.006(4) 0.011(4) 0.023(4)
  C4C 0.128(12) 0.094(10) 0.168(14) 0.060(9) 0.022(10) 0.041(10)
  N1D 0.058(4) 0.062(4) 0.066(4) 0.016(3) 0.031(3) 0.000(3)
  N2D 0.070(5) 0.097(7) 0.118(7) 0.011(5) 0.052(5) -0.022(6)
  N3D 0.075(5) 0.109(7) 0.099(6) 0.015(5) 0.049(5) 0.001(6)
  N4D 0.052(4) 0.056(4) 0.077(5) 0.010(4) 0.015(4) 0.011(4)
  C5D 0.062(5) 0.078(6) 0.056(5) 0.023(5) 0.028(4) 0.009(4)
  O5D 0.105(5) 0.129(7) 0.086(4) 0.017(5) 0.062(4) -0.010(5)
  C1D 0.049(4) 0.045(4) 0.075(5) 0.000(4) 0.021(4) 0.003(4)
  O1D 0.069(4) 0.109(6) 0.096(5) -0.005(4) 0.041(4) 0.019(4)
  O2D 0.087(4) 0.058(4) 0.103(5) 0.004(3) 0.032(4) -0.015(4)
  C2D 0.120(9) 0.059(7) 0.129(10) 0.004(7) -0.023(8) -0.027(7)
  C3D 0.094(7) 0.070(7) 0.065(6) 0.055(6) 0.027(5) 0.017(5)
  O3D 0.095(5) 0.095(5) 0.152(7) -0.012(5) 0.065(5) 0.022(5)
  O4D 0.081(4) 0.063(4) 0.091(5) -0.003(4) 0.019(4) 0.003(4)
  C4D 0.135(12) 0.133(13) 0.122(11) 0.014(10) 0.017(9) -0.032(10)
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
  N1A C5A . 1.387(12) ?
  N1A N2A . 1.392(10) ?
  N1A C1A . 1.419(12) ?
  N2A N3A . 1.257(12) ?
  N3A N4A . 1.376(11) ?
  N4A C5A . 1.404(11) ?
  N4A C3A . 1.416(13) ?
  C5A O5A . 1.187(10) ?
  C1A O1A . 1.197(11) ?
  C1A O2A . 1.313(12) ?
  O2A C2A . 1.428(13) ?
  C2A H1A . 0.9600 ?
  C2A H2A . 0.9600 ?
  C2A H3A . 0.9600 ?
  C3A O3A . 1.197(12) ?
  C3A O4A . 1.300(11) ?
  O4A C4A . 1.439(12) ?
  C4A H4A . 0.9600 ?
  C4A H5A . 0.9600 ?
  C4A H6A . 0.9600 ?
  N1B N2B . 1.366(11) ?
  N1B C5B . 1.372(10) ?
  N1B C1B . 1.409(12) ?
  N2B N3B . 1.273(11) ?
  N3B N4B . 1.391(9) ?
  N4B C5B . 1.382(12) ?
  N4B C3B . 1.402(11) ?
  C5B O5B . 1.191(10) ?
  C1B O1B . 1.174(12) ?
  C1B O2B . 1.315(11) ?
  O2B C2B . 1.484(13) ?
  C2B H1B . 0.9600 ?
  C2B H2B . 0.9600 ?
  C2B H3B . 0.9600 ?
  C3B O3B . 1.196(10) ?
  C3B O4B . 1.295(11) ?
  O4B C4B . 1.455(12) ?
  C4B H4B . 0.9600 ?
  C4B H5B . 0.9600 ?
  C4B H6B . 0.9600 ?
  N1C N2C . 1.370(11) ?
  N1C C1C . 1.377(12) ?
  N1C C5C . 1.455(12) ?
  N2C N3C . 1.182(11) ?
  N3C N4C . 1.496(13) ?
  N4C C5C . 1.322(12) ?
  N4C C3C . 1.397(12) ?
  C5C O5C . 1.146(11) ?
  C1C O2C . 1.232(13) ?
  C1C O1C . 1.237(13) ?
  O2C C2C . 1.563(13) ?
  C2C H1C . 0.9600 ?
  C2C H2C . 0.9600 ?
  C2C H3C . 0.9600 ?
  C3C O3C . 1.177(12) ?
  C3C O4C . 1.317(12) ?
  O4C C4C . 1.462(13) ?
  C4C H4C . 0.9600 ?
  C4C H5C . 0.9600 ?
  C4C H6C . 0.9600 ?
  N1D C5D . 1.395(11) ?
  N1D N2D . 1.403(11) ?
  N1D C1D . 1.418(11) ?
  N2D N3D . 1.235(12) ?
  N3D N4D . 1.410(11) ?
  N4D C5D . 1.370(12) ?
  N4D C3D . 1.463(14) ?
  C5D O5D . 1.177(10) ?
  C1D O1D . 1.176(10) ?
  C1D O2D . 1.307(11) ?
  O2D C2D . 1.449(13) ?
  C2D H1D . 0.9600 ?
  C2D H2D . 0.9600 ?
  C2D H3D . 0.9600 ?
  C3D O3D . 1.145(12) ?
  C3D O4D . 1.309(11) ?
  O4D C4D . 1.515(18) ?
  C4D H4D . 0.9600 ?
  C4D H5D . 0.9600 ?
  C4D H6D . 0.9600 ?