Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705708X/cf2150sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705708X/cf2150Isup2.hkl |
CCDC reference: 672934
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.146
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C6 - C7 ... 1.53 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C6 .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C7 .. 3.01 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O1 .. 2.64 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Fryer et al. (1977); Latypov et al. (1998, 1999); Stasko et al. (2002).
Compound (I) was prepared according to a reported method (Latypov et al., 1998). Elemental analysis and spectroscopic data (NMR and IR) were identical to data given in the literature (Latypov et al., 1998). Crystals suitable for X-ray crystallographic analysis were obtained via solvent evaporation (methanol).
All H atoms were positioned geometrically and refined as riding on their parent C or N atoms, with N—H = 0.86 Å, Uiso(H) = 1.2Ueq(C); C—H = 0.96 Å, Uiso(H) = 1.5Ue.g(C).
Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C5H8N2O3 | F(000) = 608 |
Mr = 144.13 | Dx = 1.477 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 13590 reflections |
a = 12.4940 (6) Å | θ = 1–27.5° |
b = 6.1930 (4) Å | µ = 0.12 mm−1 |
c = 16.8170 (9) Å | T = 150 K |
β = 95.054 (4)° | Block, colourless |
V = 1296.16 (13) Å3 | 0.49 × 0.19 × 0.15 mm |
Z = 8 |
Bruke–Nonius KappaCCD area-detector diffractometer | 2951 independent reflections |
Radiation source: fine-focus sealed tube | 2060 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.4° |
ϕ and ω scans | h = −16→16 |
Absorption correction: integration Gaussian integration (Coppens, 1970) | k = −7→8 |
Tmin = 0.964, Tmax = 0.989 | l = −21→21 |
12836 measured reflections |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0472P)2 + 1.5623P] where P = (Fo2 + 2Fc2)/3 |
2951 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C5H8N2O3 | V = 1296.16 (13) Å3 |
Mr = 144.13 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4940 (6) Å | µ = 0.12 mm−1 |
b = 6.1930 (4) Å | T = 150 K |
c = 16.8170 (9) Å | 0.49 × 0.19 × 0.15 mm |
β = 95.054 (4)° |
Bruke–Nonius KappaCCD area-detector diffractometer | 2951 independent reflections |
Absorption correction: integration Gaussian integration (Coppens, 1970) | 2060 reflections with I > 2σ(I) |
Tmin = 0.964, Tmax = 0.989 | Rint = 0.068 |
12836 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.50 e Å−3 |
2951 reflections | Δρmin = −0.32 e Å−3 |
181 parameters |
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. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.12247 (15) | 0.6735 (3) | −0.00306 (11) | 0.0255 (4) | |
O4 | 0.82756 (14) | 0.1748 (3) | 0.25416 (10) | 0.0241 (4) | |
O5 | 0.60291 (15) | 0.1821 (3) | 0.29300 (11) | 0.0284 (5) | |
O6 | 0.63045 (16) | 0.5268 (3) | 0.06070 (11) | 0.0302 (5) | |
N1 | 0.15534 (18) | 0.4369 (3) | 0.10251 (13) | 0.0246 (5) | |
H1 | 0.1729 | 0.5280 | 0.1400 | 0.030* | |
O3 | 0.24709 (15) | 0.1223 (3) | 0.15056 (11) | 0.0289 (5) | |
O2 | 0.09293 (15) | 0.2734 (3) | −0.09169 (10) | 0.0259 (4) | |
C6 | 0.75687 (19) | 0.2888 (4) | 0.22195 (14) | 0.0186 (5) | |
N3 | 0.76312 (17) | 0.4351 (3) | 0.16439 (12) | 0.0210 (5) | |
H3 | 0.8214 | 0.4606 | 0.1424 | 0.025* | |
N2 | 0.12607 (17) | 0.1272 (3) | 0.03429 (12) | 0.0228 (5) | |
H2 | 0.1210 | −0.0076 | 0.0222 | 0.027* | |
N4 | 0.59112 (17) | 0.4362 (4) | 0.19236 (13) | 0.0240 (5) | |
H4 | 0.5233 | 0.4619 | 0.1903 | 0.029* | |
C1 | 0.13122 (19) | 0.4949 (4) | 0.02705 (15) | 0.0187 (5) | |
C7 | 0.6399 (2) | 0.2909 (4) | 0.24181 (14) | 0.0196 (5) | |
C8 | 0.6631 (2) | 0.5476 (4) | 0.14202 (15) | 0.0224 (6) | |
C3 | 0.1494 (2) | 0.2047 (4) | 0.11601 (15) | 0.0235 (6) | |
C2 | 0.11345 (19) | 0.2841 (4) | −0.01977 (14) | 0.0188 (5) | |
C9 | 0.6684 (2) | 0.7859 (4) | 0.15861 (17) | 0.0294 (6) | |
H9A | 0.6906 | 0.8093 | 0.2141 | 0.044* | |
H9B | 0.5988 | 0.8489 | 0.1459 | 0.044* | |
H9C | 0.7193 | 0.8517 | 0.1265 | 0.044* | |
C4 | 0.0641 (2) | 0.1466 (5) | 0.17123 (16) | 0.0287 (6) | |
H4A | −0.0043 | 0.2008 | 0.1494 | 0.043* | |
H4B | 0.0822 | 0.2099 | 0.2228 | 0.043* | |
H4C | 0.0603 | −0.0075 | 0.1764 | 0.043* | |
C10 | 0.6166 (2) | 0.3104 (5) | 0.03054 (16) | 0.0331 (7) | |
H10A | 0.5943 | 0.3151 | −0.0255 | 0.050* | |
H10B | 0.5629 | 0.2378 | 0.0581 | 0.050* | |
H10C | 0.6835 | 0.2337 | 0.0389 | 0.050* | |
C5 | 0.3385 (2) | 0.1707 (5) | 0.10905 (16) | 0.0301 (6) | |
H5A | 0.4013 | 0.1081 | 0.1369 | 0.045* | |
H5B | 0.3472 | 0.3245 | 0.1062 | 0.045* | |
H5C | 0.3286 | 0.1123 | 0.0560 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0335 (10) | 0.0138 (9) | 0.0294 (10) | 0.0033 (8) | 0.0036 (8) | 0.0033 (8) |
O4 | 0.0245 (9) | 0.0237 (10) | 0.0241 (9) | 0.0044 (8) | 0.0018 (7) | 0.0062 (8) |
O5 | 0.0292 (10) | 0.0268 (11) | 0.0304 (10) | −0.0065 (9) | 0.0093 (8) | 0.0040 (8) |
O6 | 0.0388 (11) | 0.0277 (11) | 0.0228 (10) | 0.0054 (9) | −0.0053 (8) | 0.0022 (8) |
N1 | 0.0380 (13) | 0.0143 (11) | 0.0203 (11) | 0.0007 (10) | −0.0046 (9) | −0.0039 (9) |
O3 | 0.0262 (10) | 0.0329 (11) | 0.0274 (10) | 0.0030 (9) | 0.0012 (8) | 0.0079 (8) |
O2 | 0.0316 (10) | 0.0275 (11) | 0.0183 (9) | −0.0044 (8) | −0.0003 (7) | −0.0014 (8) |
C6 | 0.0218 (12) | 0.0174 (13) | 0.0167 (11) | −0.0003 (11) | 0.0031 (9) | −0.0007 (10) |
N3 | 0.0191 (10) | 0.0229 (12) | 0.0217 (11) | 0.0021 (9) | 0.0056 (8) | 0.0043 (9) |
N2 | 0.0316 (12) | 0.0116 (11) | 0.0244 (11) | 0.0003 (9) | −0.0020 (9) | −0.0028 (9) |
N4 | 0.0170 (10) | 0.0280 (13) | 0.0273 (11) | 0.0017 (9) | 0.0040 (9) | 0.0014 (10) |
C1 | 0.0176 (12) | 0.0162 (13) | 0.0226 (13) | 0.0015 (10) | 0.0033 (10) | −0.0016 (10) |
C7 | 0.0225 (12) | 0.0165 (13) | 0.0200 (12) | −0.0023 (10) | 0.0026 (10) | −0.0037 (10) |
C8 | 0.0240 (13) | 0.0228 (14) | 0.0203 (13) | 0.0040 (11) | 0.0008 (10) | 0.0025 (10) |
C3 | 0.0265 (13) | 0.0201 (14) | 0.0230 (13) | 0.0018 (11) | −0.0032 (10) | 0.0010 (10) |
C2 | 0.0163 (11) | 0.0173 (13) | 0.0229 (12) | −0.0001 (10) | 0.0015 (9) | −0.0023 (10) |
C9 | 0.0371 (15) | 0.0200 (15) | 0.0311 (14) | 0.0044 (12) | 0.0015 (12) | 0.0017 (11) |
C4 | 0.0226 (13) | 0.0323 (16) | 0.0311 (15) | 0.0002 (12) | 0.0017 (11) | 0.0064 (12) |
C10 | 0.0396 (16) | 0.0318 (17) | 0.0265 (14) | −0.0011 (14) | −0.0046 (12) | −0.0058 (12) |
C5 | 0.0240 (13) | 0.0352 (17) | 0.0318 (14) | 0.0002 (12) | 0.0064 (11) | 0.0088 (13) |
O1—C1 | 1.217 (3) | N4—C7 | 1.335 (3) |
O4—C6 | 1.220 (3) | N4—C8 | 1.461 (3) |
O5—C7 | 1.216 (3) | N4—H4 | 0.8599 |
O6—C8 | 1.398 (3) | C1—C2 | 1.531 (3) |
O6—C10 | 1.438 (3) | C8—C9 | 1.502 (4) |
N1—C1 | 1.328 (3) | C3—C4 | 1.517 (4) |
N1—C3 | 1.459 (3) | C9—H9A | 0.960 |
N1—H1 | 0.860 | C9—H9B | 0.960 |
O3—C3 | 1.401 (3) | C9—H9C | 0.960 |
O3—C5 | 1.422 (3) | C4—H4A | 0.960 |
O2—C2 | 1.216 (3) | C4—H4B | 0.960 |
C6—N3 | 1.333 (3) | C4—H4C | 0.960 |
C6—C7 | 1.528 (3) | C10—H10A | 0.960 |
N3—C8 | 1.452 (3) | C10—H10B | 0.960 |
N3—H3 | 0.860 | C10—H10C | 0.960 |
N2—C2 | 1.330 (3) | C5—H5A | 0.960 |
N2—C3 | 1.461 (3) | C5—H5B | 0.960 |
N2—H2 | 0.8599 | C5—H5C | 0.960 |
C8—O6—C10 | 116.5 (2) | N1—C3—N2 | 100.73 (19) |
C1—N1—C3 | 113.9 (2) | O3—C3—C4 | 107.1 (2) |
C1—N1—H1 | 123.0 | N1—C3—C4 | 112.1 (2) |
C3—N1—H1 | 123.1 | N2—C3—C4 | 113.9 (2) |
C3—O3—C5 | 115.3 (2) | O2—C2—N2 | 129.9 (2) |
O4—C6—N3 | 129.0 (2) | O2—C2—C1 | 124.5 (2) |
O4—C6—C7 | 125.3 (2) | N2—C2—C1 | 105.6 (2) |
N3—C6—C7 | 105.7 (2) | C8—C9—H9A | 109.5 |
C6—N3—C8 | 114.2 (2) | C8—C9—H9B | 109.5 |
C6—N3—H3 | 122.9 | H9A—C9—H9B | 109.5 |
C8—N3—H3 | 122.9 | C8—C9—H9C | 109.5 |
C2—N2—C3 | 113.9 (2) | H9A—C9—H9C | 109.5 |
C2—N2—H2 | 123.1 | H9B—C9—H9C | 109.5 |
C3—N2—H2 | 123.1 | C3—C4—H4A | 109.5 |
C7—N4—C8 | 114.1 (2) | C3—C4—H4B | 109.5 |
C7—N4—H4 | 122.9 | H4A—C4—H4B | 109.5 |
C8—N4—H4 | 122.9 | C3—C4—H4C | 109.5 |
O1—C1—N1 | 130.4 (2) | H4A—C4—H4C | 109.5 |
O1—C1—C2 | 123.9 (2) | H4B—C4—H4C | 109.5 |
N1—C1—C2 | 105.7 (2) | O6—C10—H10A | 109.5 |
O5—C7—N4 | 129.3 (2) | O6—C10—H10B | 109.5 |
O5—C7—C6 | 125.5 (2) | H10A—C10—H10B | 109.5 |
N4—C7—C6 | 105.2 (2) | O6—C10—H10C | 109.5 |
O6—C8—N3 | 112.3 (2) | H10A—C10—H10C | 109.5 |
O6—C8—N4 | 112.5 (2) | H10B—C10—H10C | 109.5 |
N3—C8—N4 | 100.5 (2) | O3—C5—H5A | 109.5 |
O6—C8—C9 | 106.1 (2) | O3—C5—H5B | 109.5 |
N3—C8—C9 | 113.6 (2) | H5A—C5—H5B | 109.5 |
N4—C8—C9 | 112.1 (2) | O3—C5—H5C | 109.5 |
O3—C3—N1 | 111.7 (2) | H5A—C5—H5C | 109.5 |
O3—C3—N2 | 111.4 (2) | H5B—C5—H5C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5i | 0.86 | 2.12 | 2.892 (3) | 149 |
N1—H1···O4i | 0.86 | 2.00 | 2.817 (3) | 159 |
N3—H3···O2ii | 0.86 | 2.18 | 2.894 (3) | 140 |
N3—H3···O1ii | 0.86 | 2.64 | 3.246 (3) | 129 |
N2—H2···O1iii | 0.86 | 2.02 | 2.878 (3) | 175 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C5H8N2O3 |
Mr | 144.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 12.4940 (6), 6.1930 (4), 16.8170 (9) |
β (°) | 95.054 (4) |
V (Å3) | 1296.16 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.49 × 0.19 × 0.15 |
Data collection | |
Diffractometer | Bruke–Nonius KappaCCD area-detector diffractometer |
Absorption correction | Integration Gaussian integration (Coppens, 1970) |
Tmin, Tmax | 0.964, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12836, 2951, 2060 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.146, 1.12 |
No. of reflections | 2951 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.32 |
Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), COLLECT and DENZO, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5i | 0.86 | 2.12 | 2.892 (3) | 148.7 |
N1—H1···O4i | 0.86 | 2.00 | 2.817 (3) | 158.5 |
N3—H3···O2ii | 0.86 | 2.18 | 2.894 (3) | 140.4 |
N3—H3···O1ii | 0.86 | 2.64 | 3.246 (3) | 128.7 |
N2—H2···O1iii | 0.86 | 2.02 | 2.878 (3) | 175.1 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x, y−1, z. |
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2-Methoxy-2-methylimidazolidine-4,5-dione is the only known example of 2-alkoxy-2-alkylimidazolidine-4,5-diones. It is an intermediate of the synthesis of the low-sensitivity energetic material 2,2-dinitroethene-1,1-diamine (Latypov et al., 1999).
The title compound (I) has been obtained as colourless crystals from a saturated methanol solution.
Two independent molecules which are positioned with an interplanar (ring to ring) angle of 88.49 (10)° are found in the asymmetric unit. The five-membered rings are formed (see Figure 1) by two N(H)—C=O fragments and one ipso carbon connected to both methoxy and methyl groups. The structure of similar cyclic compounds were determined previously (Stasko et al., 2002; Fryer et al., 1977). In both cases, a spiro derivative of imidazoline-4,5-dione (II) and benzodiazepine-1,2-dione (III) reveals very similar interatomic distances and bonding angles to those found in the title compound.
The C—O distances found in (I) [1.217 (3), 1.216 (3), 1.220 (3), and 1.216 (3) Å] are typical for double bonds between these elements. All N—H groups are bonded to C=O fragments in a similar manner to that usually found in peptides. The distances [1.531 (3) Å and 1.528 (3) Å] between the carbon atoms of C=O fragments are a little longer than found in the comparable compounds (II) and (III). All remaining interatomic distances and bonding angles are in line with those found for (II) and (III) previously.
Compound (I) forms an extensive three-dimensional network through the N—H···O=C hydrogen bonding (see Figure 2).