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In the title compound, C10H7N3O4·H2O, one carboxyl group is deprotonated and the pyridyl group is protonated. The inner salt molecule has a planar structure, apart from the carboxylic acid group, which is tilted from the imidazole plane by a small dihedral angle of 7.3 (3)°.
Supporting information
CCDC reference: 613856
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.003 Å
- R factor = 0.051
- wR factor = 0.111
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
4-carboxy-2-(pyridinium-4-yl)-1H-imidazole-5-dicarboxylate monohydrate
top
Crystal data top
C10H7N3O4·H2O | F(000) = 520 |
Mr = 251.20 | Dx = 1.627 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1068 reflections |
a = 5.6348 (15) Å | θ = 2.6–23.4° |
b = 8.457 (2) Å | µ = 0.13 mm−1 |
c = 21.605 (6) Å | T = 298 K |
β = 94.889 (4)° | Planete, yellow |
V = 1025.7 (5) Å3 | 0.26 × 0.24 × 0.03 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1912 independent reflections |
Radiation source: fine-focus sealed tube | 1541 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −4→6 |
Tmin = 0.966, Tmax = 0.990 | k = −9→10 |
5216 measured reflections | l = −26→26 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.2198P] where P = (Fo2 + 2Fc2)/3 |
1912 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | Uiso*/Ueq | |
C1 | 0.8506 (4) | 0.4838 (3) | 0.60335 (10) | 0.0281 (5) | |
C2 | 0.6719 (4) | 0.5982 (2) | 0.57526 (9) | 0.0241 (5) | |
C3 | 0.4716 (4) | 0.6694 (2) | 0.59559 (9) | 0.0253 (5) | |
C4 | 0.3661 (4) | 0.6560 (3) | 0.65615 (10) | 0.0299 (5) | |
C5 | 0.4978 (4) | 0.7506 (2) | 0.50291 (10) | 0.0255 (5) | |
C6 | 0.4441 (4) | 0.8321 (2) | 0.44343 (10) | 0.0254 (5) | |
C7 | 0.5829 (4) | 0.8191 (3) | 0.39374 (10) | 0.0319 (5) | |
H7 | 0.7196 | 0.7570 | 0.3971 | 0.038* | |
C8 | 0.5181 (4) | 0.8984 (3) | 0.33948 (10) | 0.0358 (6) | |
H8 | 0.6111 | 0.8898 | 0.3061 | 0.043* | |
C9 | 0.1834 (4) | 1.0036 (3) | 0.38145 (11) | 0.0372 (6) | |
H9 | 0.0489 | 1.0677 | 0.3769 | 0.045* | |
C10 | 0.2403 (4) | 0.9257 (3) | 0.43598 (11) | 0.0338 (6) | |
H10 | 0.1425 | 0.9352 | 0.4683 | 0.041* | |
N1 | 0.3226 (3) | 0.9874 (2) | 0.33446 (9) | 0.0358 (5) | |
H1N | 0.2734 | 1.0549 | 0.2985 | 0.054* | |
N2 | 0.3656 (3) | 0.7649 (2) | 0.55016 (8) | 0.0286 (4) | |
N3 | 0.6857 (3) | 0.6519 (2) | 0.51620 (8) | 0.0262 (4) | |
H3N | 0.7975 | 0.6222 | 0.4881 | 0.039* | |
O1 | 0.2004 (3) | 0.7393 (2) | 0.66784 (8) | 0.0473 (5) | |
O2 | 0.4564 (3) | 0.55115 (19) | 0.69540 (7) | 0.0378 (4) | |
H2A | 0.6020 | 0.5051 | 0.6838 | 0.057* | |
O3 | 0.8208 (3) | 0.43801 (19) | 0.65815 (7) | 0.0394 (4) | |
O4 | 1.0113 (3) | 0.43913 (18) | 0.57235 (7) | 0.0380 (4) | |
O5 | 0.8688 (3) | 0.79770 (19) | 0.75193 (7) | 0.0415 (4) | |
H5A | 0.9543 | 0.8453 | 0.7821 | 0.062* | |
H5B | 0.9891 | 0.7631 | 0.7311 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0261 (12) | 0.0313 (12) | 0.0268 (11) | −0.0032 (10) | 0.0024 (10) | −0.0017 (10) |
C2 | 0.0259 (11) | 0.0272 (11) | 0.0199 (10) | −0.0028 (9) | 0.0057 (9) | −0.0020 (9) |
C3 | 0.0243 (12) | 0.0283 (11) | 0.0235 (11) | −0.0012 (10) | 0.0037 (9) | −0.0018 (9) |
C4 | 0.0283 (12) | 0.0338 (13) | 0.0283 (12) | −0.0042 (11) | 0.0060 (10) | −0.0027 (10) |
C5 | 0.0270 (11) | 0.0255 (11) | 0.0244 (11) | −0.0013 (9) | 0.0049 (9) | −0.0022 (9) |
C6 | 0.0277 (12) | 0.0248 (11) | 0.0236 (11) | −0.0025 (9) | 0.0024 (9) | −0.0005 (9) |
C7 | 0.0304 (13) | 0.0366 (13) | 0.0293 (12) | 0.0018 (11) | 0.0063 (10) | 0.0002 (10) |
C8 | 0.0378 (14) | 0.0439 (14) | 0.0266 (12) | 0.0004 (12) | 0.0077 (10) | 0.0031 (11) |
C9 | 0.0309 (13) | 0.0373 (14) | 0.0432 (14) | 0.0035 (11) | 0.0019 (11) | 0.0037 (11) |
C10 | 0.0309 (13) | 0.0375 (13) | 0.0338 (12) | 0.0032 (11) | 0.0075 (10) | 0.0009 (11) |
N1 | 0.0389 (12) | 0.0379 (11) | 0.0299 (10) | −0.0025 (10) | −0.0021 (9) | 0.0074 (9) |
N2 | 0.0287 (10) | 0.0316 (10) | 0.0261 (10) | 0.0018 (8) | 0.0066 (8) | −0.0005 (8) |
N3 | 0.0256 (10) | 0.0308 (10) | 0.0231 (9) | 0.0015 (8) | 0.0068 (8) | −0.0022 (8) |
O1 | 0.0483 (11) | 0.0546 (11) | 0.0426 (10) | 0.0186 (9) | 0.0238 (9) | 0.0048 (9) |
O2 | 0.0370 (9) | 0.0514 (10) | 0.0264 (8) | 0.0069 (8) | 0.0104 (7) | 0.0064 (8) |
O3 | 0.0384 (10) | 0.0527 (11) | 0.0277 (8) | 0.0089 (8) | 0.0071 (7) | 0.0111 (8) |
O4 | 0.0356 (9) | 0.0461 (10) | 0.0338 (9) | 0.0133 (8) | 0.0116 (8) | 0.0023 (8) |
O5 | 0.0374 (10) | 0.0567 (11) | 0.0306 (9) | 0.0021 (9) | 0.0043 (7) | −0.0054 (8) |
Geometric parameters (Å, º) top
C1—O3 | 1.270 (3) | C7—C8 | 1.372 (3) |
C1—O4 | 1.230 (3) | C7—H7 | 0.9300 |
C1—C2 | 1.488 (3) | C8—N1 | 1.331 (3) |
C2—N3 | 1.363 (3) | C8—H8 | 0.9300 |
C2—C3 | 1.383 (3) | C9—N1 | 1.342 (3) |
C3—N2 | 1.369 (3) | C9—C10 | 1.364 (3) |
C3—C4 | 1.487 (3) | C9—H9 | 0.9300 |
C4—O1 | 1.213 (3) | C10—H10 | 0.9300 |
C4—O2 | 1.300 (3) | N1—H1N | 0.9842 |
C5—N2 | 1.319 (3) | N3—H3N | 0.9448 |
C5—N3 | 1.360 (3) | O2—H2A | 0.9605 |
C5—C6 | 1.467 (3) | O5—H5A | 0.8754 |
C6—C7 | 1.386 (3) | O5—H5B | 0.8950 |
C6—C10 | 1.393 (3) | | |
| | | |
O4—C1—O3 | 125.1 (2) | C6—C7—H7 | 120.1 |
O4—C1—C2 | 118.77 (19) | N1—C8—C7 | 120.3 (2) |
O3—C1—C2 | 116.1 (2) | N1—C8—H8 | 119.9 |
N3—C2—C3 | 105.40 (18) | C7—C8—H8 | 119.9 |
N3—C2—C1 | 120.52 (19) | N1—C9—C10 | 119.6 (2) |
C3—C2—C1 | 134.07 (19) | N1—C9—H9 | 120.2 |
N2—C3—C2 | 110.31 (18) | C10—C9—H9 | 120.2 |
N2—C3—C4 | 119.56 (19) | C9—C10—C6 | 120.3 (2) |
C2—C3—C4 | 130.1 (2) | C9—C10—H10 | 119.8 |
O1—C4—O2 | 121.7 (2) | C6—C10—H10 | 119.8 |
O1—C4—C3 | 120.8 (2) | C8—N1—C9 | 122.0 (2) |
O2—C4—C3 | 117.5 (2) | C8—N1—H1N | 124.6 |
N2—C5—N3 | 111.94 (19) | C9—N1—H1N | 113.2 |
N2—C5—C6 | 123.2 (2) | C5—N2—C3 | 105.09 (18) |
N3—C5—C6 | 124.9 (2) | C5—N3—C2 | 107.26 (18) |
C7—C6—C10 | 118.0 (2) | C5—N3—H3N | 125.3 |
C7—C6—C5 | 123.6 (2) | C2—N3—H3N | 127.3 |
C10—C6—C5 | 118.3 (2) | C4—O2—H2A | 113.7 |
C8—C7—C6 | 119.8 (2) | H5A—O5—H5B | 97.7 |
C8—C7—H7 | 120.1 | | |
| | | |
O4—C1—C2—N3 | 0.2 (3) | C10—C6—C7—C8 | 0.4 (3) |
O3—C1—C2—N3 | −178.67 (19) | C5—C6—C7—C8 | 179.3 (2) |
O4—C1—C2—C3 | 178.7 (2) | C6—C7—C8—N1 | 0.0 (3) |
O3—C1—C2—C3 | −0.2 (3) | N1—C9—C10—C6 | 1.2 (3) |
N3—C2—C3—N2 | −0.2 (2) | C7—C6—C10—C9 | −1.0 (3) |
C1—C2—C3—N2 | −178.9 (2) | C5—C6—C10—C9 | 180.0 (2) |
N3—C2—C3—C4 | 179.9 (2) | C7—C8—N1—C9 | 0.2 (3) |
C1—C2—C3—C4 | 1.3 (4) | C10—C9—N1—C8 | −0.8 (3) |
N2—C3—C4—O1 | −6.7 (3) | N3—C5—N2—C3 | −0.8 (2) |
C2—C3—C4—O1 | 173.1 (2) | C6—C5—N2—C3 | 178.87 (19) |
N2—C3—C4—O2 | 172.59 (18) | C2—C3—N2—C5 | 0.6 (2) |
C2—C3—C4—O2 | −7.6 (3) | C4—C3—N2—C5 | −179.51 (19) |
N2—C5—C6—C7 | 179.3 (2) | N2—C5—N3—C2 | 0.7 (2) |
N3—C5—C6—C7 | −1.0 (3) | C6—C5—N3—C2 | −178.98 (19) |
N2—C5—C6—C10 | −1.7 (3) | C3—C2—N3—C5 | −0.3 (2) |
N3—C5—C6—C10 | 177.91 (19) | C1—C2—N3—C5 | 178.61 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O5i | 0.98 | 1.80 | 2.758 (2) | 164 |
N3—H3N···O4ii | 0.94 | 1.84 | 2.779 (2) | 174 |
O2—H2A···O3 | 0.96 | 1.51 | 2.462 (2) | 173 |
O5—H5B···O1iii | 0.90 | 1.90 | 2.759 (2) | 161 |
O5—H5A···O3iv | 0.88 | 1.90 | 2.768 (2) | 172 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, y+1/2, −z+3/2. |
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