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The title compound, C7H7NO3·2H2O, exists as a betaine. The O atoms of the hydroxy and carboxylate groups of 3-hydroxypyridinium-1-acetate interact with water molecules to form a three-dimensional hydrogen-bonded supramolecular network.
Supporting information
CCDC reference: 289630
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.113
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 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 dihydrate
top
Crystal data top
C7H7NO3·2H2O | Z = 2 |
Mr = 189.17 | F(000) = 200 |
Triclinic, P1 | Dx = 1.446 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9055 (14) Å | Cell parameters from 3575 reflections |
b = 7.0086 (14) Å | θ = 3.2–27.5° |
c = 10.074 (2) Å | µ = 0.12 mm−1 |
α = 71.62 (3)° | T = 295 K |
β = 76.09 (3)° | Prism, colorless |
γ = 71.93 (3)° | 0.32 × 0.25 × 0.18 mm |
V = 434.34 (18) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1964 independent reflections |
Radiation source: fine-focus sealed tube | 1540 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −8→7 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→9 |
Tmin = 0.961, Tmax = 0.978 | l = −13→13 |
4289 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.076P] where = P = (Fo2 + 2Fc2)/3 |
1964 reflections | (Δ/σ)max < 0.001 |
133 parameters | Δρmax = 0.28 e Å−3 |
7 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1W | 0.99046 (19) | 0.27444 (19) | 0.15643 (16) | 0.0705 (4) | |
H1W1 | 0.904 (3) | 0.393 (2) | 0.131 (3) | 0.106* | |
H1W2 | 1.105 (2) | 0.283 (4) | 0.099 (2) | 0.106* | |
O2W | 0.7696 (2) | 0.9840 (2) | 0.23527 (14) | 0.0701 (4) | |
H2W1 | 0.839 (3) | 1.076 (3) | 0.208 (3) | 0.105* | |
H2W2 | 0.664 (3) | 1.031 (4) | 0.193 (3) | 0.105* | |
O1 | 0.43843 (18) | 0.19172 (18) | 1.08790 (11) | 0.0542 (3) | |
O2 | 0.33578 (18) | 0.3908 (2) | 0.88503 (15) | 0.0727 (4) | |
O3 | 0.7123 (2) | 0.82908 (16) | 0.50564 (12) | 0.0553 (3) | |
H8 | 0.729 (4) | 0.878 (3) | 0.4151 (11) | 0.083* | |
N1 | 0.71951 (16) | 0.32632 (17) | 0.73416 (11) | 0.0346 (3) | |
C1 | 0.4677 (2) | 0.2776 (2) | 0.95851 (15) | 0.0408 (3) | |
C2 | 0.6930 (2) | 0.2334 (2) | 0.88853 (14) | 0.0401 (3) | |
H2A | 0.7697 | 0.2877 | 0.9307 | 0.048* | |
H2B | 0.7504 | 0.0842 | 0.9070 | 0.048* | |
C3 | 0.7063 (2) | 0.5302 (2) | 0.68688 (14) | 0.0368 (3) | |
H3 | 0.6834 | 0.6082 | 0.7512 | 0.044* | |
C4 | 0.7265 (2) | 0.6261 (2) | 0.54320 (14) | 0.0371 (3) | |
C5 | 0.7591 (2) | 0.5069 (2) | 0.44944 (14) | 0.0411 (3) | |
H5 | 0.7739 | 0.5670 | 0.3523 | 0.049* | |
C6 | 0.7693 (2) | 0.2981 (2) | 0.50249 (16) | 0.0456 (4) | |
H6 | 0.7904 | 0.2169 | 0.4404 | 0.055* | |
C7 | 0.7486 (2) | 0.2082 (2) | 0.64544 (15) | 0.0418 (3) | |
H7 | 0.7546 | 0.0672 | 0.6806 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1W | 0.0468 (7) | 0.0510 (7) | 0.0911 (10) | −0.0104 (5) | 0.0049 (6) | −0.0015 (7) |
O2W | 0.0853 (10) | 0.0688 (8) | 0.0540 (7) | −0.0382 (7) | −0.0172 (7) | 0.0099 (6) |
O1 | 0.0621 (7) | 0.0656 (7) | 0.0387 (5) | −0.0297 (6) | 0.0114 (5) | −0.0201 (5) |
O2 | 0.0382 (6) | 0.0876 (10) | 0.0714 (8) | 0.0046 (6) | −0.0055 (6) | −0.0150 (7) |
O3 | 0.0762 (8) | 0.0370 (6) | 0.0502 (6) | −0.0189 (5) | −0.0124 (6) | −0.0019 (5) |
N1 | 0.0313 (5) | 0.0354 (6) | 0.0334 (5) | −0.0068 (4) | −0.0020 (4) | −0.0076 (4) |
C1 | 0.0415 (7) | 0.0401 (7) | 0.0430 (7) | −0.0132 (6) | 0.0033 (6) | −0.0185 (6) |
C2 | 0.0390 (7) | 0.0412 (7) | 0.0330 (6) | −0.0086 (6) | −0.0031 (5) | −0.0037 (5) |
C3 | 0.0388 (7) | 0.0366 (7) | 0.0369 (7) | −0.0105 (5) | −0.0038 (5) | −0.0127 (5) |
C4 | 0.0343 (6) | 0.0355 (7) | 0.0393 (7) | −0.0103 (5) | −0.0051 (5) | −0.0058 (5) |
C5 | 0.0400 (7) | 0.0498 (8) | 0.0318 (6) | −0.0127 (6) | −0.0042 (5) | −0.0083 (6) |
C6 | 0.0504 (8) | 0.0477 (8) | 0.0427 (7) | −0.0119 (7) | −0.0025 (6) | −0.0216 (6) |
C7 | 0.0451 (7) | 0.0339 (7) | 0.0449 (7) | −0.0090 (6) | −0.0031 (6) | −0.0124 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.2475 (18) | O3—H8 | 0.860 (10) |
O2—C1 | 1.230 (2) | O1W—H1W1 | 0.86 (2) |
O3—C4 | 1.3301 (17) | O1W—H1W2 | 0.87 (2) |
N1—C2 | 1.4746 (17) | O2W—H2W1 | 0.86 (2) |
N1—C3 | 1.3369 (17) | O2W—H2W2 | 0.86 (2) |
N1—C7 | 1.3422 (19) | C2—H2A | 0.9700 |
C1—C2 | 1.525 (2) | C2—H2B | 0.9700 |
C3—C4 | 1.3834 (19) | C3—H3 | 0.9300 |
C4—C5 | 1.385 (2) | C5—H5 | 0.9300 |
C5—C6 | 1.376 (2) | C6—H6 | 0.9300 |
C6—C7 | 1.370 (2) | C7—H7 | 0.9300 |
| | | |
O1—C1—C2 | 114.54 (13) | N1—C2—H2B | 109.0 |
O2—C1—O1 | 126.86 (14) | N1—C3—H3 | 119.7 |
O2—C1—C2 | 118.59 (13) | N1—C7—H7 | 120.4 |
O3—C4—C3 | 116.58 (13) | C1—C2—H2A | 109.0 |
O3—C4—C5 | 124.77 (13) | C1—C2—H2B | 109.0 |
N1—C2—C1 | 112.77 (11) | C4—O3—H8 | 111.5 (16) |
N1—C3—C4 | 120.64 (13) | C4—C3—H3 | 119.7 |
N1—C7—C6 | 119.14 (13) | C4—C5—H5 | 120.6 |
C3—N1—C7 | 121.76 (12) | C5—C6—H6 | 119.5 |
C3—N1—C2 | 118.20 (12) | C6—C5—H5 | 120.6 |
C3—C4—C5 | 118.65 (12) | C6—C7—H7 | 120.4 |
C6—C5—C4 | 118.90 (13) | C7—C6—H6 | 119.5 |
C7—N1—C2 | 120.00 (12) | H2A—C2—H2B | 107.8 |
C7—C6—C5 | 120.90 (14) | H1W1—O1W—H1W2 | 105.8 (13) |
N1—C2—H2A | 109.0 | H2W1—O2W—H2W2 | 108.5 (14) |
| | | |
O1—C1—C2—N1 | 176.19 (12) | C3—N1—C2—C1 | 77.57 (16) |
O2—C1—C2—N1 | −3.8 (2) | C3—N1—C7—C6 | 1.3 (2) |
O3—C4—C5—C6 | −179.55 (13) | C3—C4—C5—C6 | 0.3 (2) |
N1—C3—C4—O3 | −179.67 (12) | C4—C5—C6—C7 | −0.3 (2) |
N1—C3—C4—C5 | 0.47 (19) | C5—C6—C7—N1 | −0.5 (2) |
C2—N1—C3—C4 | −178.92 (12) | C7—N1—C2—C1 | −100.12 (15) |
C2—N1—C7—C6 | 178.87 (12) | C7—N1—C3—C4 | −1.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2i | 0.86 (2) | 1.87 (2) | 2.704 (2) | 164 (2) |
O1W—H1W2···O1ii | 0.87 (2) | 2.18 (2) | 2.9147 (18) | 143 (2) |
O1W—H1W2···O2ii | 0.87 (2) | 2.41 (2) | 3.239 (2) | 159 (2) |
O2W—H2W1···O1Wiii | 0.86 (2) | 1.87 (2) | 2.725 (2) | 178 (2) |
O2W—H2W2···O1iv | 0.86 (2) | 1.94 (3) | 2.785 (2) | 168 (2) |
O3—H8···O2W | 0.86 (1) | 1.72 (2) | 2.5764 (19) | 177 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z−1; (iii) x, y+1, z; (iv) x, y+1, z−1. |
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