Di­methyl 5-oxo-4,5-di­hydro-1H-tetrazole-1,4-di­carboxyl­ate

Crockett, R.; Forrester, A.R.; Howie, R.A.

doi:10.1107/S1600536803018282

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Dimethyl 5-oxo-4,5-dihydro-1H-tetrazole-1,4-dicarboxylate

R. Crockett, A. R. Forrester and R. A. Howie

A notable feature of the structure of the title compound, C₅H₆N₄O₅, is the presence of four crystallographically independent and essentially planar but otherwise unremarkable molecules in the asymmetric unit. The molecules are distributed as two pairs which differ in conformation from one pair to the other in the orientation of one of the carbomethoxy substituents relative to the tetrazole ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018282/bt6328sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018282/bt6328Isup2.hkl Contains datablock I

CCDC reference: 222890

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (N-C) = 0.013 Å
R factor = 0.085
wR factor = 0.247
Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.89

Author Response: ... The intensity data used in this analysis dates back to the early 1980's when, in this laboratory, it was acceptable practice, in the course of data reduction, to elliminate reflections with negative intensities from the data. Since the crystals are no longer available there is no easy possibility of obtaining a new and more complete set of intensity data.


Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N4D    -   C3D      =       7.89 su
PLAT432_ALERT_2_B Short Inter X...Y Contact  O1C    ..  C1B      =       2.82 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O5B    ..  C1D      =       2.80 Ang.

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.603
            Test value =      0.600
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.12
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1C    -   C5C      =       5.36 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3C    -   N4C      =       6.01 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O4D    -   C3D      =       6.20 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        N2C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C3A
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C3B
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N1C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C3C
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        O4D
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C1D
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1A    ..  C3D      =       3.01 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3C    ..  C5A      =       2.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5C    ..  C5B      =       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5D    ..  C3C      =       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  N3C    ..  C1A      =       2.97 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.04
           From the CIF: _reflns_number_total               4147
           Count of symmetry unique reflns         5266
           Completeness (_total/calc)             78.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  20 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  20 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The asymmetric unit of the title compound, (I), contains four crystallographically independent molecules. The constituent atoms of all four molecules have been labelled in an identical manner except that the individual molecules are identified by the suffix A, B, C or D. The molecules can be considered in pairs as A with B (Fig. 1) and C with D (Fig. 2), which clearly differ in the orientation of one carbomethoxy group relative to the tetrazole ring. As can be seen in Table 1, which compares the geometric parameters for all four molecules, the only values, aside from the torsion angles about the C3—N4 bond, which are sensitive to the change in conformation are the C3—N4—C5 and C3—N4—N3 angles. Aside from this the bond lengths and angles are fully consistent with the connectivity and bond types indicated in the Scheme.

Experimental top

Compound (I) was prepared by saturating a vigorously stirred ice-cold solution of tetrazol-5-one (Haines et al., 1982) (1.72 g, 0.02 mol) and dry pyridine (3.96 g, 0.05 mol) in anhydrous diethyl ether (100 ml) with gaseous phosgene (COCl₂), allowing the solution come to room temperature (298 K) and continuing stirring for a further 10 min before the addition of methanol (10 ml) and further pyridine (3.96 g, 0.05 mol). After filtration removal of solvent from the filtrate furnished solid (I) which was recrystallized from diethyl ether to provide crystals suitable for analysis.

Computing details top

Data collection: Nicolet P3 Software (Nicolet, 1980); cell refinement: Nicolet P3 Software; data reduction: RDNIC (Howie, 1980); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecule A of (I) showing the labelling scheme and the conformation of the molecule both of which apply also to molecule B. Non-H atoms are shown as 30% probability displacement ellipsoids and H atoms as small circles.
	Fig. 2. The labelling scheme and molecular conformation of molecules C and D of (I). The example shown is molecule C and the representation is otherwise the same as in Fig. 1.

Dimethyl 5-oxo-4,5-dihydro-1,2,3,4-tetrazole-1,4-dicarboxylate top

Crystal data top

C₅H₆N₄O₅	F(000) = 832
M_r = 202.14	D_x = 1.540 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.023 (17) Å	Cell parameters from 14 reflections
b = 15.92 (3) Å	θ = 8.0–11.5°
c = 12.123 (15) Å	µ = 0.14 mm⁻¹
β = 115.67 (11)°	T = 298 K
V = 1744 (5) Å³	Block, colourless
Z = 8	0.64 × 0.50 × 0.34 mm

Data collection top

Nicolet P3 diffractometer	R_int = 0.000
Radiation source: normal-focus sealed tube	θ_max = 30.0°, θ_min = 1.9°
Graphite monochromator	h = 0→14
θ–2θ scans	k = 0→22
4147 measured reflections	l = −17→15
4147 independent reflections	2 standard reflections every 50 reflections
2144 reflections with I > 2σ(I)	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.247	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1438P)²] where P = (F_o² + 2F_c²)/3
4147 reflections	(Δ/σ)_max < 0.001
505 parameters	Δρ_max = 0.60 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₅H₆N₄O₅	V = 1744 (5) Å³
M_r = 202.14	Z = 8
Monoclinic, P2₁	Mo Kα radiation
a = 10.023 (17) Å	µ = 0.14 mm⁻¹
b = 15.92 (3) Å	T = 298 K
c = 12.123 (15) Å	0.64 × 0.50 × 0.34 mm
β = 115.67 (11)°

Data collection top

Nicolet P3 diffractometer	R_int = 0.000
4147 measured reflections	2 standard reflections every 50 reflections
4147 independent reflections	intensity decay: none
2144 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.085	1 restraint
wR(F²) = 0.247	H-atom parameters constrained
S = 1.00	Δρ_max = 0.60 e Å⁻³
4147 reflections	Δρ_min = −0.28 e Å⁻³
505 parameters

Special details top

Experimental. Scan rates, dependent on prescan intensity (Ip), were in the range 58.6 (Ip>2500) to 5.33 (Ip<150) ° 2θ min⁻¹. Scan widths, dependent on 2θ, were in the range 2.4 to 2.8 ° 2θ. Stationary crystal, stationary counter background counts were taken on either side of the peak each for 25% of the total (peak plus background) count time.

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

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

− 6.4440 (0.1151) x − 1.5602 (0.1522) y + 11.6765 (0.0611) z = 1.4619 (0.2909)

* 0.0000 (0.0001) O1A * 0.0000 (0.0001) C1A * 0.0000 (0.0000) O2A 0.0874 (0.0323) C2A

Rms deviation of fitted atoms = 0.0000

− 5.9882 (0.0332) x − 3.0427 (0.0656) y + 11.6472 (0.0259) z = 0.3469 (0.0665)

Angle to previous plane (with approximate e.s.d.) = 6.04 (1.17)

* −0.0078 (0.0048) N1A * 0.0016 (0.0051) N2A * 0.0058 (0.0052) N3A * −0.0104 (0.0050) N4A * 0.0107 (0.0046) C5A −0.0049 (0.0127) O5A 0.1748 (0.0150) O1A 0.0645 (0.0130) C1A −0.0623 (0.0148) O2A 0.0181 (0.0216) C2A −0.1502 (0.0163) O3A −0.0176 (0.0133) C3A 0.0278 (0.0138) O4A −0.0376 (0.0209) C4A

Rms deviation of fitted atoms = 0.0080

5.8090 (0.0762) x + 4.8613 (0.2204) y − 11.2994 (0.0835) z = 1.1935 (0.2396)

Angle to previous plane (with approximate e.s.d.) = 6.76 (1.12)

* 0.0000 (0.0001) O3A * 0.0000 (0.0001) C3A * 0.0000 (0.0000) O4A −0.0577 (0.0316) C4A

Rms deviation of fitted atoms = 0.0000

− 5.9186 (0.0871) x + 4.0506 (0.2165) y + 11.4696 (0.0776) z = 6.9000 (0.0530)

Angle to previous plane (with approximate e.s.d.) = 32.51 (1.05)

* 0.0000 (0.0000) O1B * 0.0000 (0.0000) C1B * 0.0000 (0.0000) O2B 0.0031 (0.0328) C2B

Rms deviation of fitted atoms = 0.0000

− 6.1750 (0.0309) x + 3.7824 (0.0594) y + 11.4413 (0.0263) z = 6.8745 (0.0191)

Angle to previous plane (with approximate e.s.d.) = 1.95 (1.18)

* −0.0078 (0.0044) N1B * 0.0074 (0.0045) N2B * −0.0038 (0.0043) N3B * −0.0011 (0.0042) N4B * 0.0052 (0.0043) C5B −0.0522 (0.0118) O5B −0.1097 (0.0141) O1B −0.0799 (0.0128) C1B −0.0357 (0.0130) O2B −0.0208 (0.0208) C2B −0.0034 (0.0140) O3B −0.0618 (0.0122) C3B −0.1327 (0.0137) O4B −0.2493 (0.0214) C4B

Rms deviation of fitted atoms = 0.0056

− 6.4053 (0.1115) x + 2.9317 (0.1350) y + 11.5159 (0.0680) z = 6.6195 (0.0793)

Angle to previous plane (with approximate e.s.d.) = 3.34 (1.22)

* 0.0000 (0.0000) O3B * 0.0000 (0.0000) C3B * 0.0000 (0.0000) O4B −0.1085 (0.0321) C4B

Rms deviation of fitted atoms = 0.0000

− 9.0321 (0.0766) x − 6.0281 (0.1392) y + 7.0408 (0.1553) z = 2.8781 (0.0679)

Angle to previous plane (with approximate e.s.d.) = 48.40 (1.15)

* 0.0000 (0.0001) O1C * 0.0000 (0.0001) C1C * 0.0000 (0.0000) O2C 0.0032 (0.0369) C2C

Rms deviation of fitted atoms = 0.0000

− 9.0030 (0.0239) x − 6.4164 (0.0561) y + 6.6345 (0.0419) z = 2.4307 (0.0491)

Angle to previous plane (with approximate e.s.d.) = 2.49 (1.16)

* −0.0005 (0.0044) N1C * 0.0044 (0.0053) N2C * −0.0061 (0.0049) N3C * 0.0055 (0.0045) N4C * −0.0033 (0.0043) C5C −0.0082 (0.0118) O5C 0.0192 (0.0150) O1C −0.0344 (0.0131) C1C −0.0675 (0.0140) O2C −0.0322 (0.0212) C2C −0.1003 (0.0151) O3C −0.0165 (0.0128) C3C 0.0586 (0.0147) O4C 0.0079 (0.0246) C4C

Rms deviation of fitted atoms = 0.0044

− 8.9913 (0.0896) x − 5.8990 (0.2159) y + 7.3431 (0.1009) z = 3.3458 (0.0902)

Angle to previous plane (with approximate e.s.d.) = 4.19 (1.39)

* 0.0000 (0.0002) O3C * 0.0000 (0.0001) C3C * 0.0000 (0.0000) O4C −0.0222 (0.0375) C4C

Rms deviation of fitted atoms = 0.0000

− 2.4950(0.1313) x + 12.5808(0.1569) y − 4.8133(0.0532) z = 10.0608(0.2448)

Angle to previous plane (with approximate e.s.d.) = 78.21 (1.02)

* 0.0000 (0.0000) O1D * 0.0000 (0.0000) C1D * 0.0000 (0.0000) O2D −0.1472 (0.0319) C2D

Rms deviation of fitted atoms = 0.0000

− 2.7569 (0.0437) x + 11.2720 (0.0536) y − 5.6638 (0.0503) z = 8.5867 (0.0560)

Angle to previous plane (with approximate e.s.d.) = 7.16 (1.25)

* 0.0137 (0.0050) N1D * −0.0084 (0.0058) N2D * −0.0008 (0.0056) N3D * 0.0095 (0.0049) N4D * −0.0140 (0.0046) C5D 0.0056 (0.0141) O5D −0.1671 (0.0165) O1D −0.1837 (0.0137) C1D −0.3189 (0.0159) O2D −0.6215 (0.0234) C2D −0.1467 (0.0167) O3D −0.1003 (0.0140) C3D −0.1451 (0.0153) O4D −0.2414 (0.0268) C4D

Rms deviation of fitted atoms = 0.0104

− 3.1562 (0.1021) x + 10.1842 (0.2447) y − 6.0086 (0.0741) z = 7.5299 (0.2090)

Angle to previous plane (with approximate e.s.d.) = 5.38 (1.75)

* 0.0000 (0.0000) O3D * 0.0000 (0.0000) C3D * 0.0000 (0.0000) O4D 0.0456 (0.0378) C4D

Rms deviation of fitted atoms = 0.0000

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.7832 (7)	0.9408 (5)	0.6776 (6)	0.0612 (18)
N2A	0.6546 (9)	0.9887 (6)	0.6248 (8)	0.078 (2)
N3A	0.5497 (8)	0.9415 (6)	0.5589 (7)	0.074 (2)
N4A	0.6056 (7)	0.8618 (5)	0.5654 (6)	0.0603 (18)
C5A	0.7574 (9)	0.8570 (6)	0.6440 (8)	0.061 (2)
O5A	0.8408 (6)	0.7995 (4)	0.6705 (6)	0.0744 (17)
C1A	0.9190 (10)	0.9760 (7)	0.7628 (8)	0.068 (2)
O1A	1.0264 (7)	0.9336 (5)	0.8164 (6)	0.088 (2)
O2A	0.9074 (8)	1.0579 (5)	0.7673 (6)	0.086 (2)
C2A	1.0365 (13)	1.1007 (9)	0.8518 (12)	0.113 (5)
H1A	1.0365	1.1019	0.9309	0.170*
H2A	1.0367	1.1571	0.8240	0.170*
H3A	1.1233	1.0718	0.8573	0.170*
C3A	0.5176 (10)	0.7925 (6)	0.5014 (8)	0.063 (2)
O3A	0.5691 (8)	0.7251 (5)	0.4989 (7)	0.099 (2)
O4A	0.3804 (7)	0.8155 (5)	0.4408 (7)	0.083 (2)
C4A	0.2790 (10)	0.7521 (7)	0.3664 (9)	0.080 (3)
H4A	0.3300	0.7138	0.3368	0.119*
H5A	0.1992	0.7782	0.2983	0.119*
H6A	0.2400	0.7219	0.4146	0.119*
N1B	0.0776 (7)	0.2916 (4)	0.5457 (6)	0.0555 (16)
N2B	0.0287 (8)	0.2117 (6)	0.5470 (7)	0.066 (2)
N3B	0.1341 (8)	0.1651 (5)	0.6183 (7)	0.0616 (17)
N4B	0.2579 (7)	0.2169 (4)	0.6682 (6)	0.0497 (15)
C5B	0.2250 (9)	0.2980 (6)	0.6242 (7)	0.057 (2)
O5B	0.3049 (7)	0.3571 (4)	0.6428 (6)	0.0796 (18)
C1B	−0.0130 (10)	0.3554 (6)	0.4693 (7)	0.063 (2)
O1B	0.0323 (8)	0.4233 (5)	0.4687 (6)	0.0846 (19)
O2B	−0.1487 (7)	0.3266 (5)	0.4095 (6)	0.0798 (19)
C2B	−0.2541 (11)	0.3915 (9)	0.3325 (10)	0.100 (4)
H1B	−0.2162	0.4462	0.3633	0.151*
H2B	−0.3480	0.3837	0.3345	0.151*
H3B	−0.2664	0.3864	0.2497	0.151*
C3B	0.3968 (9)	0.1853 (5)	0.7484 (7)	0.0551 (19)
O3B	0.5033 (7)	0.2293 (5)	0.7964 (6)	0.087 (2)
O4B	0.3894 (7)	0.1054 (4)	0.7646 (6)	0.0811 (19)
C4B	0.5287 (13)	0.0650 (9)	0.8429 (11)	0.103 (4)
H4B	0.6009	0.0769	0.8129	0.154*
H5B	0.5141	0.0054	0.8427	0.154*
H6B	0.5630	0.0860	0.9249	0.154*
N1C	0.0401 (6)	0.4396 (4)	0.8459 (6)	0.0488 (14)
N2C	0.0876 (10)	0.4835 (6)	0.9535 (8)	0.083 (2)
N3C	0.1773 (9)	0.4487 (7)	1.0399 (7)	0.081 (2)
N4C	0.1993 (7)	0.3660 (5)	0.9916 (7)	0.0633 (18)
C5C	0.1171 (9)	0.3594 (6)	0.8724 (9)	0.060 (2)
O5C	0.1068 (8)	0.3059 (4)	0.8059 (6)	0.0764 (17)
C1C	−0.0599 (11)	0.4690 (7)	0.7335 (10)	0.078 (3)
O1C	−0.1010 (8)	0.4236 (5)	0.6419 (6)	0.095 (2)
O2C	−0.0997 (7)	0.5406 (5)	0.7437 (9)	0.105 (3)
C2C	−0.2199 (14)	0.5770 (8)	0.6213 (11)	0.106 (4)
H1C	−0.2147	0.5486	0.5534	0.159*
H2C	−0.2025	0.6360	0.6167	0.159*
H3C	−0.3162	0.5690	0.6185	0.159*
C3C	0.3038 (10)	0.3144 (6)	1.0802 (10)	0.069 (2)
O3C	0.3747 (8)	0.3341 (6)	1.1829 (7)	0.102 (3)
O4C	0.3064 (7)	0.2431 (5)	1.0261 (7)	0.093 (2)
C4C	0.4150 (16)	0.1835 (9)	1.1081 (14)	0.145 (6)
H4C	0.5130	0.2043	1.1297	0.217*
H5C	0.4028	0.1302	1.0677	0.217*
H6C	0.4005	0.1767	1.1809	0.217*
N1D	0.4752 (7)	0.9605 (5)	0.1618 (6)	0.0606 (18)
N2D	0.3769 (10)	0.9618 (6)	0.2161 (9)	0.091 (3)
N3D	0.2763 (9)	0.9109 (7)	0.1625 (8)	0.090 (3)
N4D	0.3025 (7)	0.8716 (5)	0.0696 (7)	0.0665 (19)
C5D	0.4309 (9)	0.9005 (6)	0.0688 (7)	0.065 (2)
O5D	0.4863 (9)	0.8831 (6)	0.0038 (7)	0.099 (2)
C1D	0.6122 (9)	1.0038 (5)	0.2161 (8)	0.059 (2)
O1D	0.6957 (7)	1.0033 (5)	0.1716 (6)	0.089 (2)
O2D	0.6190 (7)	1.0424 (4)	0.3135 (7)	0.0860 (19)
C2D	0.7561 (14)	1.0860 (8)	0.3869 (12)	0.130 (6)
H1D	0.8351	1.0459	0.4212	0.195*
H2D	0.7462	1.1159	0.4517	0.195*
H3D	0.7777	1.1249	0.3363	0.195*
C3D	0.1946 (13)	0.8050 (7)	0.0091 (9)	0.079 (3)
O3D	0.0990 (9)	0.7898 (6)	0.0335 (9)	0.110 (3)
O4D	0.2383 (7)	0.7726 (4)	−0.0689 (6)	0.0849 (19)
C4D	0.1302 (17)	0.7034 (12)	−0.1370 (13)	0.144 (6)
H4D	0.1270	0.6629	−0.0794	0.215*
H5D	0.1616	0.6763	−0.1925	0.215*
H6D	0.0334	0.7270	−0.1821	0.215*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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)

Geometric parameters (Å, º) top

N1A—C5A	1.387 (12)	N1C—N2C	1.370 (11)
N1A—N2A	1.392 (10)	N1C—C1C	1.377 (12)
N1A—C1A	1.419 (12)	N1C—C5C	1.455 (12)
N2A—N3A	1.257 (12)	N2C—N3C	1.182 (11)
N3A—N4A	1.376 (11)	N3C—N4C	1.496 (13)
N4A—C5A	1.404 (11)	N4C—C5C	1.322 (12)
N4A—C3A	1.416 (13)	N4C—C3C	1.397 (12)
C5A—O5A	1.187 (10)	C5C—O5C	1.146 (11)
C1A—O1A	1.197 (11)	C1C—O2C	1.232 (13)
C1A—O2A	1.313 (12)	C1C—O1C	1.237 (13)
O2A—C2A	1.428 (13)	O2C—C2C	1.563 (13)
C2A—H1A	0.9600	C2C—H1C	0.9600
C2A—H2A	0.9600	C2C—H2C	0.9600
C2A—H3A	0.9600	C2C—H3C	0.9600
C3A—O3A	1.197 (12)	C3C—O3C	1.177 (12)
C3A—O4A	1.300 (11)	C3C—O4C	1.317 (12)
O4A—C4A	1.439 (12)	O4C—C4C	1.462 (13)
C4A—H4A	0.9600	C4C—H4C	0.9600
C4A—H5A	0.9600	C4C—H5C	0.9600
C4A—H6A	0.9600	C4C—H6C	0.9600
N1B—N2B	1.366 (11)	N1D—C5D	1.395 (11)
N1B—C5B	1.372 (10)	N1D—N2D	1.403 (11)
N1B—C1B	1.409 (12)	N1D—C1D	1.418 (11)
N2B—N3B	1.273 (11)	N2D—N3D	1.235 (12)
N3B—N4B	1.391 (9)	N3D—N4D	1.410 (11)
N4B—C5B	1.382 (12)	N4D—C5D	1.370 (12)
N4B—C3B	1.402 (11)	N4D—C3D	1.463 (14)
C5B—O5B	1.191 (10)	C5D—O5D	1.177 (10)
C1B—O1B	1.174 (12)	C1D—O1D	1.176 (10)
C1B—O2B	1.315 (11)	C1D—O2D	1.307 (11)
O2B—C2B	1.484 (13)	O2D—C2D	1.449 (13)
C2B—H1B	0.9600	C2D—H1D	0.9600
C2B—H2B	0.9600	C2D—H2D	0.9600
C2B—H3B	0.9600	C2D—H3D	0.9600
C3B—O3B	1.196 (10)	C3D—O3D	1.145 (12)
C3B—O4B	1.295 (11)	C3D—O4D	1.309 (11)
O4B—C4B	1.455 (12)	O4D—C4D	1.515 (18)
C4B—H4B	0.9600	C4D—H4D	0.9600
C4B—H5B	0.9600	C4D—H5D	0.9600
C4B—H6B	0.9600	C4D—H6D	0.9600

C5A—N1A—N2A	112.0 (8)	N2C—N1C—C1C	124.9 (8)
C5A—N1A—C1A	126.3 (8)	N2C—N1C—C5C	107.7 (7)
N2A—N1A—C1A	121.6 (8)	C1C—N1C—C5C	127.3 (8)
N3A—N2A—N1A	108.6 (8)	N3C—N2C—N1C	115.0 (9)
N2A—N3A—N4A	107.9 (7)	N2C—N3C—N4C	104.5 (7)
N3A—N4A—C5A	112.6 (8)	C5C—N4C—C3C	134.3 (9)
N3A—N4A—C3A	123.1 (7)	C5C—N4C—N3C	111.7 (8)
C5A—N4A—C3A	124.3 (7)	C3C—N4C—N3C	113.9 (8)
O5A—C5A—N1A	130.0 (8)	O5C—C5C—N4C	130.7 (9)
O5A—C5A—N4A	130.9 (9)	O5C—C5C—N1C	128.3 (8)
N1A—C5A—N4A	99.0 (7)	N4C—C5C—N1C	101.1 (8)
O1A—C1A—O2A	127.8 (10)	O2C—C1C—O1C	129.4 (11)
O1A—C1A—N1A	121.8 (10)	O2C—C1C—N1C	110.1 (10)
O2A—C1A—N1A	110.4 (8)	O1C—C1C—N1C	120.4 (10)
C1A—O2A—C2A	115.8 (9)	C1C—O2C—C2C	113.5 (10)
O2A—C2A—H1A	109.5	O2C—C2C—H1C	109.5
O2A—C2A—H2A	109.5	O2C—C2C—H2C	109.5
H1A—C2A—H2A	109.5	H1C—C2C—H2C	109.5
O2A—C2A—H3A	109.5	O2C—C2C—H3C	109.5
H1A—C2A—H3A	109.5	H1C—C2C—H3C	109.5
H2A—C2A—H3A	109.5	H2C—C2C—H3C	109.5
O3A—C3A—O4A	126.9 (10)	O3C—C3C—O4C	128.5 (10)
O3A—C3A—N4A	122.7 (8)	O3C—C3C—N4C	124.4 (10)
O4A—C3A—N4A	110.2 (8)	O4C—C3C—N4C	107.1 (9)
C3A—O4A—C4A	116.3 (8)	C3C—O4C—C4C	113.0 (9)
O4A—C4A—H4A	109.5	O4C—C4C—H4C	109.5
O4A—C4A—H5A	109.5	O4C—C4C—H5C	109.5
H4A—C4A—H5A	109.5	H4C—C4C—H5C	109.5
O4A—C4A—H6A	109.5	O4C—C4C—H6C	109.5
H4A—C4A—H6A	109.5	H4C—C4C—H6C	109.5
H5A—C4A—H6A	109.5	H5C—C4C—H6C	109.5
N2B—N1B—C5B	110.2 (7)	C5D—N1D—N2D	110.2 (8)
N2B—N1B—C1B	123.2 (7)	C5D—N1D—C1D	127.9 (7)
C5B—N1B—C1B	126.6 (7)	N2D—N1D—C1D	120.7 (7)
N3B—N2B—N1B	110.7 (7)	N3D—N2D—N1D	108.9 (8)
N2B—N3B—N4B	105.8 (7)	N2D—N3D—N4D	108.6 (8)
C5B—N4B—N3B	111.6 (6)	C5D—N4D—N3D	110.9 (8)
C5B—N4B—C3B	127.0 (7)	C5D—N4D—C3D	137.1 (9)
N3B—N4B—C3B	121.3 (7)	N3D—N4D—C3D	111.7 (8)
O5B—C5B—N1B	128.6 (9)	O5D—C5D—N4D	130.0 (10)
O5B—C5B—N4B	129.5 (8)	O5D—C5D—N1D	128.6 (9)
N1B—C5B—N4B	101.7 (7)	N4D—C5D—N1D	101.4 (7)
O1B—C1B—O2B	128.9 (10)	O1D—C1D—O2D	130.5 (9)
O1B—C1B—N1B	121.8 (8)	O1D—C1D—N1D	121.5 (8)
O2B—C1B—N1B	109.2 (8)	O2D—C1D—N1D	108.0 (8)
C1B—O2B—C2B	112.9 (8)	C1D—O2D—C2D	116.4 (9)
O2B—C2B—H1B	109.5	O2D—C2D—H1D	109.5
O2B—C2B—H2B	109.5	O2D—C2D—H2D	109.5
H1B—C2B—H2B	109.5	H1D—C2D—H2D	109.5
O2B—C2B—H3B	109.5	O2D—C2D—H3D	109.5
H1B—C2B—H3B	109.5	H1D—C2D—H3D	109.5
H2B—C2B—H3B	109.5	H2D—C2D—H3D	109.5
O3B—C3B—O4B	126.9 (9)	O3D—C3D—O4D	133.0 (12)
O3B—C3B—N4B	122.4 (8)	O3D—C3D—N4D	122.9 (10)
O4B—C3B—N4B	110.7 (7)	O4D—C3D—N4D	104.0 (10)
C3B—O4B—C4B	115.6 (8)	C3D—O4D—C4D	107.2 (10)
O4B—C4B—H4B	109.5	O4D—C4D—H4D	109.5
O4B—C4B—H5B	109.5	O4D—C4D—H5D	109.5
H4B—C4B—H5B	109.5	H4D—C4D—H5D	109.5
O4B—C4B—H6B	109.5	O4D—C4D—H6D	109.5
H4B—C4B—H6B	109.5	H4D—C4D—H6D	109.5
H5B—C4B—H6B	109.5	H5D—C4D—H6D	109.5

C5A—N1A—N2A—N3A	−0.9 (10)	C1C—N1C—N2C—N3C	−177.8 (8)
C1A—N1A—N2A—N3A	−176.3 (7)	C5C—N1C—N2C—N3C	0.6 (10)
N1A—N2A—N3A—N4A	−0.4 (10)	N1C—N2C—N3C—N4C	−1.1 (10)
N2A—N3A—N4A—C5A	1.6 (10)	N2C—N3C—N4C—C5C	1.2 (9)
N2A—N3A—N4A—C3A	−179.7 (7)	N2C—N3C—N4C—C3C	179.5 (7)
N2A—N1A—C5A—O5A	179.1 (9)	C3C—N4C—C5C—O5C	1.6 (16)
C1A—N1A—C5A—O5A	−5.8 (14)	N3C—N4C—C5C—O5C	179.4 (9)
N2A—N1A—C5A—N4A	1.7 (8)	C3C—N4C—C5C—N1C	−178.6 (8)
C1A—N1A—C5A—N4A	176.8 (7)	N3C—N4C—C5C—N1C	−0.8 (8)
N3A—N4A—C5A—O5A	−179.3 (9)	N2C—N1C—C5C—O5C	−180.0 (9)
C3A—N4A—C5A—O5A	2.0 (14)	C1C—N1C—C5C—O5C	−1.6 (13)
N3A—N4A—C5A—N1A	−2.0 (9)	N2C—N1C—C5C—N4C	0.2 (8)
C3A—N4A—C5A—N1A	179.3 (7)	C1C—N1C—C5C—N4C	178.5 (7)
C5A—N1A—C1A—O1A	−1.3 (13)	N2C—N1C—C1C—O2C	0.4 (12)
N2A—N1A—C1A—O1A	173.3 (8)	C5C—N1C—C1C—O2C	−177.7 (7)
C5A—N1A—C1A—O2A	176.1 (8)	N2C—N1C—C1C—O1C	−177.0 (8)
N2A—N1A—C1A—O2A	−9.3 (11)	C5C—N1C—C1C—O1C	4.9 (13)
O1A—C1A—O2A—C2A	−3.9 (14)	O1C—C1C—O2C—C2C	0.1 (15)
N1A—C1A—O2A—C2A	178.9 (8)	N1C—C1C—O2C—C2C	−177.0 (7)
N3A—N4A—C3A—O3A	173.2 (9)	C5C—N4C—C3C—O3C	174.3 (9)
C5A—N4A—C3A—O3A	−8.2 (13)	N3C—N4C—C3C—O3C	−3.4 (13)
N3A—N4A—C3A—O4A	−1.6 (11)	C5C—N4C—C3C—O4C	−5.1 (13)
C5A—N4A—C3A—O4A	176.9 (7)	N3C—N4C—C3C—O4C	177.2 (7)
O3A—C3A—O4A—C4A	2.6 (14)	O3C—C3C—O4C—C4C	−0.9 (16)
N4A—C3A—O4A—C4A	177.2 (7)	N4C—C3C—O4C—C4C	178.4 (9)
C5B—N1B—N2B—N3B	−1.6 (9)	C5D—N1D—N2D—N3D	−2.2 (11)
C1B—N1B—N2B—N3B	176.1 (7)	C1D—N1D—N2D—N3D	−170.8 (8)
N1B—N2B—N3B—N4B	1.1 (8)	N1D—N2D—N3D—N4D	0.7 (11)
N2B—N3B—N4B—C5B	−0.3 (8)	N2D—N3D—N4D—C5D	1.0 (11)
N2B—N3B—N4B—C3B	−177.6 (7)	N2D—N3D—N4D—C3D	175.0 (8)
N2B—N1B—C5B—O5B	176.9 (8)	N3D—N4D—C5D—O5D	−178.8 (10)
C1B—N1B—C5B—O5B	−0.7 (13)	C3D—N4D—C5D—O5D	9.5 (16)
N2B—N1B—C5B—N4B	1.3 (8)	N3D—N4D—C5D—N1D	−2.2 (8)
C1B—N1B—C5B—N4B	−176.4 (7)	C3D—N4D—C5D—N1D	−174.0 (8)
N3B—N4B—C5B—O5B	−176.2 (8)	N2D—N1D—C5D—O5D	179.2 (10)
C3B—N4B—C5B—O5B	0.9 (13)	C1D—N1D—C5D—O5D	−13.2 (15)
N3B—N4B—C5B—N1B	−0.6 (8)	N2D—N1D—C5D—N4D	2.6 (9)
C3B—N4B—C5B—N1B	176.5 (7)	C1D—N1D—C5D—N4D	170.2 (7)
N2B—N1B—C1B—O1B	−178.9 (8)	C5D—N1D—C1D—O1D	13.6 (13)
C5B—N1B—C1B—O1B	−1.6 (13)	N2D—N1D—C1D—O1D	−180.0 (8)
N2B—N1B—C1B—O2B	4.2 (11)	C5D—N1D—C1D—O2D	−168.6 (8)
C5B—N1B—C1B—O2B	−178.4 (7)	N2D—N1D—C1D—O2D	−2.2 (10)
O1B—C1B—O2B—C2B	−0.1 (14)	O1D—C1D—O2D—C2D	−6.5 (14)
N1B—C1B—O2B—C2B	176.4 (7)	N1D—C1D—O2D—C2D	176.0 (8)
C5B—N4B—C3B—O3B	6.4 (12)	C5D—N4D—C3D—O3D	173.9 (10)
N3B—N4B—C3B—O3B	−176.7 (8)	N3D—N4D—C3D—O3D	2.2 (12)
C5B—N4B—C3B—O4B	−176.0 (7)	C5D—N4D—C3D—O4D	−5.1 (12)
N3B—N4B—C3B—O4B	0.8 (10)	N3D—N4D—C3D—O4D	−176.9 (7)
O3B—C3B—O4B—C4B	−4.7 (14)	O3D—C3D—O4D—C4D	1.8 (15)
N4B—C3B—O4B—C4B	177.9 (8)	N4D—C3D—O4D—C4D	−179.3 (8)

Experimental details

Crystal data
Chemical formula	C₅H₆N₄O₅
M_r	202.14
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.023 (17), 15.92 (3), 12.123 (15)
β (°)	115.67 (11)
V (Å³)	1744 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.64 × 0.50 × 0.34

Data collection
Diffractometer	Nicolet P3 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4147, 4147, 2144
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.085, 0.247, 1.00
No. of reflections	4147
No. of parameters	505
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.28

Computer programs: Nicolet P3 Software (Nicolet, 1980), Nicolet P3 Software, RDNIC (Howie, 1980), SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 and PLATON (Spek, 2003).

Comparison Table of bond lengths and angles (Å, °) for molecules A, B, C and D of (I) top

C1—N1—N2	121.6 (8)	123.2 (7)	124.9 (8)	120.7 (7)
O1—C1—N1	121.8 (10)	121.8 (8)	120.4 (10)	121.5 (8)
O2—C1—N1	110.4 (8)	109.2 (8)	110.1 (10)	108.0 (8)
O1—C1—O2	127.8 (10)	128.9 (10)	129.4 (11)	130.5 (9)
C2—O2—C1	115.8 (9)	112.9 (8)	113.5 (10)	116.4 (9)
C3—N4—C5	124.3 (7)	127.0 (7)	134.3 (9)	137.1 (9)
C3—N4—N3	123.1 (7)	121.3 (7)	113.9 (8)	111.7 (8)
O3—C3—N4	122.7 (8)	122.4 (8)	124.4 (10)	122.9 (10)
O4—C3—N4	110.2 (8)	110.7 (7)	107.1 (9)	104.0 (10)
O3—C3—O4	126.9 (10)	126.9 (9)	128.5 (10)	133.0 (12)
C4—O4—C3	116.3 (8)	115.6 (8)	113.0 (9)	107.2 (10)
O1—C1—N1—C5	-1.3 (13)	-1.6 (13)	4.9 (13)	13.6 (13)
O1—C1—N1—N2	173.3 (8)	-178.9 (8)	-177.0 (8)	-180.0 (8)
O2—C1—N1—C5	176.1 (8)	-178.4 (7)	-177.7 (7)	-168.6 (8)
O2—C1—N1—N2	-9.3 (11)	4.2 (11)	0.4 (12)	-2.2 (10)
O3—C3—N4—C5	-8.2 (13)	6.4 (12)	174.3 (9)	173.9 (10)
O3—C3—N4—N3	173.2 (9)	-176.7 (8)	-3.4 (13)	2.2 (12)
O4—C3—N4—C5	176.9 (7)	-176.0 (7)	-5.1 (13)	-5.1 (12)
O4—C3—N4—N3	-1.6 (11)	0.8 (10)	177.2 (7)	-176.9 (7)

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Di­methyl 5-oxo-4,5-di­hydro-1H-tetrazole-1,4-di­carboxyl­ate

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Dimethyl 5-oxo-4,5-dihydro-1H-tetrazole-1,4-dicarboxylate