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The hydrolysis of ethyl 1-methyl-4-nitro-1H-imidazole-2-carboxylate leads to 1-methyl-4-nitro-1H-imidazol-2-carboxylic acid, which crystallizes as a dihydrate, C5H5N3O4·2H2O. The planar organic entity is a flat molecule; the molecules are linked through the water molecules by hydrogen bonding into a three-dimensional network.
Supporting information
CCDC reference: 289655
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.109
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
Prism
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT701_ALERT_1_C Bond Calc 1.2183(16), Rep 1.220(2), Dev.. 1.06 Sigma
O4 -N3 1.555 1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
H2 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
1-Methyl-4-nitro-1
H-imidazole-2-carboxylic acid dihydrate
top
Crystal data top
C5H5N3O4·2H2O | F(000) = 432 |
Mr = 207.15 | Dx = 1.556 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 890 reflections |
a = 7.5163 (9) Å | θ = 2.7–27.0° |
b = 12.199 (2) Å | µ = 0.14 mm−1 |
c = 9.730 (1) Å | T = 295 K |
β = 97.735 (2)° | Yellow, prism |
V = 884.1 (2) Å3 | 0.50 × 0.24 × 0.19 mm |
Z = 4 | |
Data collection top
Bruker SMART area-detector diffractometer | 1504 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 27.0°, θmin = 2.7° |
φ and ω scans | h = −9→8 |
5110 measured reflections | k = −15→14 |
1931 independent reflections | l = −12→12 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0631P)2 + 0.1428P] where P = (Fo2 + 2Fc2)/3 |
1931 reflections | (Δ/σ)max = 0.001 |
150 parameters | Δρmax = 0.33 e Å−3 |
6 restraints | Δρmin = −0.16 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.8235 (2) | 0.3133 (1) | 0.5368 (1) | 0.0548 (3) | |
O2 | 0.6369 (2) | 0.2930 (1) | 0.3407 (1) | 0.0664 (4) | |
O4 | 0.8741 (2) | 0.7178 (1) | 0.6823 (1) | 0.0645 (4) | |
O3 | 0.7244 (2) | 0.8195 (1) | 0.5274 (2) | 0.0734 (4) | |
O1w | 0.9850 (2) | 0.4593 (1) | 0.7828 (1) | 0.0552 (3) | |
O2w | 1.1566 (2) | 0.6051 (1) | 0.9722 (1) | 0.0561 (3) | |
N1 | 0.7771 (2) | 0.5339 (1) | 0.5314 (1) | 0.0371 (3) | |
N2 | 0.6005 (2) | 0.5294 (1) | 0.3286 (1) | 0.0388 (3) | |
N3 | 0.7781 (2) | 0.7305 (1) | 0.5722 (1) | 0.0488 (3) | |
C1 | 0.7169 (2) | 0.3491 (1) | 0.4301 (1) | 0.0410 (3) | |
C2 | 0.7002 (2) | 0.4704 (1) | 0.4306 (1) | 0.0366 (3) | |
C3 | 0.4954 (2) | 0.4899 (2) | 0.1997 (2) | 0.0525 (4) | |
C4 | 0.6150 (2) | 0.6358 (1) | 0.3659 (2) | 0.0426 (3) | |
C5 | 0.7237 (2) | 0.6359 (1) | 0.4901 (1) | 0.0390 (3) | |
H1 | 0.8254 | 0.2461 | 0.5354 | 0.086 (7)* | |
H1w1 | 0.924 (2) | 0.481 (2) | 0.707 (1) | 0.073 (6)* | |
H1w2 | 1.027 (3) | 0.397 (1) | 0.772 (2) | 0.080 (7)* | |
H2w1 | 1.098 (2) | 0.571 (2) | 0.905 (1) | 0.070 (6)* | |
H2w2 | 1.124 (3) | 0.584 (2) | 1.047 (1) | 0.084 (7)* | |
H3a | 0.4468 | 0.5514 | 0.1456 | 0.077 (6)* | |
H3b | 0.3990 | 0.4443 | 0.2219 | 0.074 (6)* | |
H3c | 0.5716 | 0.4482 | 0.1476 | 0.076 (6)* | |
H4 | 0.5624 | 0.6959 | 0.3176 | 0.044 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.071 (1) | 0.035 (1) | 0.053 (1) | 0.005 (1) | −0.013 (1) | 0.000 (1) |
O2 | 0.082 (1) | 0.047 (1) | 0.062 (1) | −0.001 (1) | −0.021 (1) | −0.015 (1) |
O4 | 0.081 (1) | 0.052 (1) | 0.055 (1) | −0.003 (1) | −0.012 (1) | −0.011 (1) |
O3 | 0.090 (1) | 0.036 (1) | 0.090 (1) | 0.004 (1) | −0.007 (1) | 0.002 (1) |
O1w | 0.070 (1) | 0.049 (1) | 0.042 (1) | 0.007 (1) | −0.011 (1) | −0.001 (1) |
O2w | 0.070 (1) | 0.042 (1) | 0.054 (1) | −0.013 (1) | 0.000 (1) | −0.001 (1) |
N1 | 0.040 (1) | 0.035 (1) | 0.035 (1) | 0.000 (1) | 0.001 (1) | 0.000 (1) |
N2 | 0.038 (1) | 0.044 (1) | 0.033 (1) | 0.001 (1) | 0.000 (1) | 0.002 (1) |
N3 | 0.052 (1) | 0.039 (1) | 0.055 (1) | −0.003 (1) | 0.005 (1) | −0.003 (1) |
C1 | 0.044 (1) | 0.039 (1) | 0.039 (1) | 0.000 (1) | 0.001 (1) | −0.004 (1) |
C2 | 0.037 (1) | 0.038 (1) | 0.034 (1) | 0.000 (1) | 0.002 (1) | 0.000 (1) |
C3 | 0.051 (1) | 0.067 (1) | 0.036 (1) | 0.002 (1) | −0.009 (1) | 0.001 (1) |
C4 | 0.044 (1) | 0.040 (1) | 0.044 (1) | 0.005 (1) | 0.004 (1) | 0.007 (1) |
C5 | 0.042 (1) | 0.034 (1) | 0.041 (1) | 0.000 (1) | 0.005 (1) | 0.001 (1) |
Geometric parameters (Å, º) top
O1—C1 | 1.299 (2) | C4—C5 | 1.365 (2) |
O2—C1 | 1.203 (2) | O1—H1 | 0.82 |
O4—N3 | 1.220 (2) | O1w—H1w1 | 0.85 (1) |
O3—N3 | 1.217 (2) | O1w—H1w2 | 0.84 (1) |
N1—C2 | 1.321 (2) | O2w—H2w1 | 0.85 (1) |
N1—C5 | 1.352 (2) | O2w—H2w2 | 0.84 (1) |
N2—C4 | 1.348 (2) | C3—H3a | 0.96 |
N2—C2 | 1.365 (2) | C3—H3b | 0.96 |
N2—C3 | 1.470 (2) | C3—H3c | 0.96 |
N3—C5 | 1.431 (2) | C4—H4 | 0.93 |
C1—C2 | 1.485 (2) | | |
| | | |
C2—N1—C5 | 103.7 (1) | N1—C5—C4 | 112.3 (1) |
C4—N2—C2 | 107.2 (1) | N1—C5—N3 | 121.7 (1) |
C4—N2—C3 | 124.0 (1) | C4—C5—N3 | 126.0 (1) |
C2—N2—C3 | 128.8 (1) | C1—O1—H1 | 109.5 |
O3—N3—O4 | 123.8 (1) | H1w1—O1w—H1w2 | 109 (1) |
O3—N3—C5 | 117.6 (1) | H2w1—O2w—H2w2 | 110 (1) |
O4—N3—C5 | 118.6 (1) | N2—C3—H3a | 109.5 |
O2—C1—O1 | 125.6 (1) | N2—C3—H3b | 109.5 |
O2—C1—C2 | 122.4 (1) | H3a—C3—H3b | 109.5 |
O1—C1—C2 | 112.1 (1) | N2—C3—H3c | 109.5 |
N1—C2—N2 | 111.9 (1) | H3a—C3—H3c | 109.5 |
N1—C2—C1 | 123.9 (1) | H3b—C3—H3c | 109.5 |
N2—C2—C1 | 124.2 (1) | N2—C4—H4 | 127.6 |
N2—C4—C5 | 104.9 (1) | C5—C4—H4 | 127.6 |
| | | |
C5—N1—C2—N2 | −0.2 (2) | C2—N2—C4—C5 | −0.1 (2) |
C5—N1—C2—C1 | −178.9 (1) | C3—N2—C4—C5 | −179.7 (1) |
C4—N2—C2—N1 | 0.2 (2) | C2—N1—C5—C4 | 0.2 (2) |
C3—N2—C2—N1 | 179.8 (1) | C2—N1—C5—N3 | 179.7 (1) |
C4—N2—C2—C1 | 178.9 (1) | N2—C4—C5—N1 | 0.0 (2) |
C3—N2—C2—C1 | −1.5 (2) | N2—C4—C5—N3 | −179.6 (1) |
O2—C1—C2—N1 | 175.7 (2) | O3—N3—C5—N1 | 179.9 (1) |
O1—C1—C2—N1 | −3.3 (2) | O4—N3—C5—N1 | −0.5 (2) |
O2—C1—C2—N2 | −2.9 (2) | O3—N3—C5—C4 | −0.7 (2) |
O1—C1—C2—N2 | 178.1 (1) | O4—N3—C5—C4 | 179.0 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2wi | 0.82 | 1.73 | 2.546 (2) | 176 |
O1w—H1w1···N1 | 0.85 (1) | 2.02 (1) | 2.868 (2) | 179 (2) |
O1w—H1w2···O4i | 0.84 (1) | 2.33 (1) | 3.134 (2) | 161 (2) |
O2w—H2w1···O1w | 0.85 (1) | 1.93 (1) | 2.754 (2) | 165 (2) |
O2w—H2w2···O1wii | 0.84 (1) | 2.01 (1) | 2.848 (2) | 173 (2) |
C4—H4···O2iii | 0.93 | 2.32 | 3.206 (2) | 158 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, −y+1, −z+2; (iii) −x+1, y+1/2, −z+1/2. |
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