organic compounds
In the betaine title compound, C7H7NO3·H2O or HOC5H4N+CH2CO2-·H2O, 3-hydroxypyridinium-1-acetate interacts with the water molecule to form a two-dimensional hydrogen-bonded framework.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031284/wn6386sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031284/wn6386Isup2.hkl |
CCDC reference: 289926
Computing details top
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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.
3-Hydroxypyridinium-1-acetate monohydrate top
Crystal data top
C7H7NO3·H2O | F(000) = 720 |
Mr = 171.15 | Dx = 1.492 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 11630 reflections |
a = 8.8417 (18) Å | θ = 3.2–27.4° |
b = 12.081 (2) Å | µ = 0.12 mm−1 |
c = 14.262 (3) Å | T = 295 K |
V = 1523.5 (5) Å3 | Sheet, colorless |
Z = 8 | 0.39 × 0.26 × 0.15 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1742 independent reflections |
Radiation source: fine-focus sealed tube | 1459 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −10→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.962, Tmax = 0.982 | l = −18→18 |
13670 measured reflections |
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) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.3906P] where P = (Fo2 + 2Fc2)/3 |
1742 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.24 e Å−3 |
4 restraints | Δρmin = −0.17 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.31758 (11) | 0.51318 (9) | 0.57668 (7) | 0.0313 (2) | |
O1 | 0.07838 (11) | 0.72021 (8) | 0.47208 (7) | 0.0469 (3) | |
O2 | 0.03068 (11) | 0.59901 (9) | 0.58574 (7) | 0.0468 (3) | |
O3 | 0.21185 (12) | 0.26155 (8) | 0.68717 (8) | 0.0465 (3) | |
O1W | 0.23655 (12) | 0.17515 (9) | 0.85056 (7) | 0.0466 (3) | |
C1 | 0.24669 (14) | 0.41753 (10) | 0.59572 (9) | 0.0330 (3) | |
C2 | 0.28868 (14) | 0.35515 (10) | 0.67290 (9) | 0.0335 (3) | |
C3 | 0.40521 (15) | 0.39337 (11) | 0.72963 (9) | 0.0399 (3) | |
C4 | 0.47644 (15) | 0.49159 (12) | 0.70689 (11) | 0.0428 (3) | |
C5 | 0.43166 (14) | 0.55080 (11) | 0.62998 (10) | 0.0379 (3) | |
C6 | 0.26069 (15) | 0.58282 (11) | 0.49949 (9) | 0.0372 (3) | |
C7 | 0.10961 (14) | 0.63974 (11) | 0.52294 (9) | 0.0334 (3) | |
H1 | 0.1691 | 0.3931 | 0.5569 | 0.040* | |
H3 | 0.4349 | 0.3534 | 0.7822 | 0.048* | |
H4 | 0.5552 | 0.5176 | 0.7441 | 0.051* | |
H5 | 0.4800 | 0.6167 | 0.6147 | 0.045* | |
H7 | 0.230 (2) | 0.2352 (15) | 0.7428 (8) | 0.070* | |
H1W1 | 0.1468 (12) | 0.1630 (15) | 0.8708 (12) | 0.070* | |
H1W2 | 0.2851 (17) | 0.2113 (15) | 0.8923 (11) | 0.070* | |
H6A | 0.2474 | 0.5373 | 0.4441 | 0.045* | |
H6B | 0.3355 | 0.6390 | 0.4850 | 0.045* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0286 (5) | 0.0309 (5) | 0.0343 (5) | 0.0045 (4) | 0.0026 (4) | 0.0006 (4) |
O1 | 0.0402 (5) | 0.0476 (6) | 0.0530 (6) | 0.0083 (4) | −0.0021 (4) | 0.0147 (5) |
O2 | 0.0371 (5) | 0.0542 (6) | 0.0491 (6) | 0.0080 (4) | 0.0117 (4) | 0.0109 (5) |
O3 | 0.0535 (6) | 0.0375 (5) | 0.0486 (6) | −0.0104 (4) | −0.0070 (5) | 0.0085 (4) |
O1W | 0.0396 (6) | 0.0573 (7) | 0.0430 (6) | −0.0083 (5) | 0.0042 (4) | 0.0024 (5) |
C1 | 0.0309 (6) | 0.0335 (7) | 0.0345 (6) | 0.0000 (5) | −0.0012 (5) | −0.0034 (5) |
C2 | 0.0330 (6) | 0.0307 (6) | 0.0368 (7) | 0.0021 (5) | 0.0020 (5) | −0.0014 (5) |
C3 | 0.0374 (7) | 0.0428 (7) | 0.0394 (7) | 0.0040 (6) | −0.0055 (5) | 0.0035 (6) |
C4 | 0.0346 (7) | 0.0448 (7) | 0.0489 (8) | −0.0027 (6) | −0.0109 (6) | −0.0042 (6) |
C5 | 0.0302 (6) | 0.0330 (6) | 0.0504 (8) | −0.0011 (5) | 0.0004 (5) | −0.0026 (6) |
C6 | 0.0361 (7) | 0.0388 (7) | 0.0366 (7) | 0.0049 (5) | 0.0044 (5) | 0.0076 (5) |
C7 | 0.0304 (6) | 0.0356 (6) | 0.0343 (6) | 0.0004 (5) | −0.0035 (5) | 0.0002 (5) |
Geometric parameters (Å, º) top
N1—C5 | 1.3423 (17) | C6—C7 | 1.5392 (18) |
N1—C1 | 1.3424 (16) | O3—H7 | 0.870 (9) |
N1—C6 | 1.4741 (16) | O1W—H1W1 | 0.858 (9) |
O1—C7 | 1.2440 (16) | O1W—H1W2 | 0.854 (9) |
O2—C7 | 1.2375 (16) | C1—H1 | 0.9300 |
O3—C2 | 1.3348 (16) | C3—H3 | 0.9300 |
C1—C2 | 1.3847 (18) | C4—H4 | 0.9300 |
C2—C3 | 1.3890 (18) | C5—H5 | 0.9300 |
C3—C4 | 1.382 (2) | C6—H6A | 0.9700 |
C4—C5 | 1.368 (2) | C6—H6B | 0.9700 |
N1—C1—C2 | 120.27 (11) | N1—C5—H5 | 120.2 |
N1—C5—C4 | 119.64 (12) | N1—C6—H6A | 109.0 |
N1—C6—C7 | 112.88 (10) | N1—C6—H6B | 109.0 |
O1—C7—C6 | 114.52 (11) | C2—O3—H7 | 110.7 (13) |
O2—C7—O1 | 127.42 (12) | C2—C1—H1 | 119.9 |
O2—C7—C6 | 117.97 (11) | C2—C3—H3 | 120.4 |
O3—C2—C1 | 116.48 (12) | C3—C4—H4 | 119.8 |
O3—C2—C3 | 124.77 (12) | C4—C3—H3 | 120.4 |
C1—N1—C6 | 118.89 (11) | C4—C5—H5 | 120.2 |
C1—C2—C3 | 118.75 (12) | C5—C4—H4 | 119.8 |
C4—C3—C2 | 119.13 (12) | C7—C6—H6A | 109.0 |
C5—N1—C1 | 121.85 (11) | C7—C6—H6B | 109.0 |
C5—N1—C6 | 119.09 (11) | H1W1—O1W—H1W2 | 108.5 (12) |
C5—C4—C3 | 120.34 (13) | H6A—C6—H6B | 107.8 |
N1—C1—H1 | 119.9 | ||
N1—C1—C2—O3 | 179.57 (11) | C1—C2—C3—C4 | −0.62 (19) |
N1—C1—C2—C3 | −0.16 (18) | C2—C3—C4—C5 | 0.6 (2) |
N1—C6—C7—O2 | −21.42 (17) | C3—C4—C5—N1 | 0.2 (2) |
N1—C6—C7—O1 | 161.72 (11) | C5—N1—C1—C2 | 1.00 (18) |
O3—C2—C3—C4 | 179.68 (13) | C5—N1—C6—C7 | −103.56 (13) |
C1—N1—C5—C4 | −1.03 (19) | C6—N1—C1—C2 | −174.19 (11) |
C1—N1—C6—C7 | 71.76 (15) | C6—N1—C5—C4 | 174.15 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2i | 0.86 (1) | 1.86 (1) | 2.6934 (14) | 165 (2) |
O1W—H1W2···O1ii | 0.85 (1) | 1.85 (1) | 2.6980 (15) | 170 (2) |
O3—H7···O1W | 0.87 (1) | 1.70 (1) | 2.5627 (15) | 171 (2) |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x+1/2, −y+1, z+1/2. |