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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031442/at6038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031442/at6038Isup2.hkl
Contains datablock I

CCDC reference: 289630

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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
C7H7NO3·2H2OZ = 2
Mr = 189.17F(000) = 200
Triclinic, P1Dx = 1.446 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9055 (14) ÅCell parameters from 3575 reflections
b = 7.0086 (14) Åθ = 3.2–27.5°
c = 10.074 (2) ŵ = 0.12 mm1
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 tube1540 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 87
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 99
Tmin = 0.961, Tmax = 0.978l = 1313
4289 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H 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 parametersΔρmax = 0.28 e Å3
7 restraintsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1W0.99046 (19)0.27444 (19)0.15643 (16)0.0705 (4)
H1W10.904 (3)0.393 (2)0.131 (3)0.106*
H1W21.105 (2)0.283 (4)0.099 (2)0.106*
O2W0.7696 (2)0.9840 (2)0.23527 (14)0.0701 (4)
H2W10.839 (3)1.076 (3)0.208 (3)0.105*
H2W20.664 (3)1.031 (4)0.193 (3)0.105*
O10.43843 (18)0.19172 (18)1.08790 (11)0.0542 (3)
O20.33578 (18)0.3908 (2)0.88503 (15)0.0727 (4)
O30.7123 (2)0.82908 (16)0.50564 (12)0.0553 (3)
H80.729 (4)0.878 (3)0.4151 (11)0.083*
N10.71951 (16)0.32632 (17)0.73416 (11)0.0346 (3)
C10.4677 (2)0.2776 (2)0.95851 (15)0.0408 (3)
C20.6930 (2)0.2334 (2)0.88853 (14)0.0401 (3)
H2A0.76970.28770.93070.048*
H2B0.75040.08420.90700.048*
C30.7063 (2)0.5302 (2)0.68688 (14)0.0368 (3)
H30.68340.60820.75120.044*
C40.7265 (2)0.6261 (2)0.54320 (14)0.0371 (3)
C50.7591 (2)0.5069 (2)0.44944 (14)0.0411 (3)
H50.77390.56700.35230.049*
C60.7693 (2)0.2981 (2)0.50249 (16)0.0456 (4)
H60.79040.21690.44040.055*
C70.7486 (2)0.2082 (2)0.64544 (15)0.0418 (3)
H70.75460.06720.68060.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.0468 (7)0.0510 (7)0.0911 (10)0.0104 (5)0.0049 (6)0.0015 (7)
O2W0.0853 (10)0.0688 (8)0.0540 (7)0.0382 (7)0.0172 (7)0.0099 (6)
O10.0621 (7)0.0656 (7)0.0387 (5)0.0297 (6)0.0114 (5)0.0201 (5)
O20.0382 (6)0.0876 (10)0.0714 (8)0.0046 (6)0.0055 (6)0.0150 (7)
O30.0762 (8)0.0370 (6)0.0502 (6)0.0189 (5)0.0124 (6)0.0019 (5)
N10.0313 (5)0.0354 (6)0.0334 (5)0.0068 (4)0.0020 (4)0.0076 (4)
C10.0415 (7)0.0401 (7)0.0430 (7)0.0132 (6)0.0033 (6)0.0185 (6)
C20.0390 (7)0.0412 (7)0.0330 (6)0.0086 (6)0.0031 (5)0.0037 (5)
C30.0388 (7)0.0366 (7)0.0369 (7)0.0105 (5)0.0038 (5)0.0127 (5)
C40.0343 (6)0.0355 (7)0.0393 (7)0.0103 (5)0.0051 (5)0.0058 (5)
C50.0400 (7)0.0498 (8)0.0318 (6)0.0127 (6)0.0042 (5)0.0083 (6)
C60.0504 (8)0.0477 (8)0.0427 (7)0.0119 (7)0.0025 (6)0.0216 (6)
C70.0451 (7)0.0339 (7)0.0449 (7)0.0090 (6)0.0031 (6)0.0124 (6)
Geometric parameters (Å, º) top
O1—C11.2475 (18)O3—H80.860 (10)
O2—C11.230 (2)O1W—H1W10.86 (2)
O3—C41.3301 (17)O1W—H1W20.87 (2)
N1—C21.4746 (17)O2W—H2W10.86 (2)
N1—C31.3369 (17)O2W—H2W20.86 (2)
N1—C71.3422 (19)C2—H2A0.9700
C1—C21.525 (2)C2—H2B0.9700
C3—C41.3834 (19)C3—H30.9300
C4—C51.385 (2)C5—H50.9300
C5—C61.376 (2)C6—H60.9300
C6—C71.370 (2)C7—H70.9300
O1—C1—C2114.54 (13)N1—C2—H2B109.0
O2—C1—O1126.86 (14)N1—C3—H3119.7
O2—C1—C2118.59 (13)N1—C7—H7120.4
O3—C4—C3116.58 (13)C1—C2—H2A109.0
O3—C4—C5124.77 (13)C1—C2—H2B109.0
N1—C2—C1112.77 (11)C4—O3—H8111.5 (16)
N1—C3—C4120.64 (13)C4—C3—H3119.7
N1—C7—C6119.14 (13)C4—C5—H5120.6
C3—N1—C7121.76 (12)C5—C6—H6119.5
C3—N1—C2118.20 (12)C6—C5—H5120.6
C3—C4—C5118.65 (12)C6—C7—H7120.4
C6—C5—C4118.90 (13)C7—C6—H6119.5
C7—N1—C2120.00 (12)H2A—C2—H2B107.8
C7—C6—C5120.90 (14)H1W1—O1W—H1W2105.8 (13)
N1—C2—H2A109.0H2W1—O2W—H2W2108.5 (14)
O1—C1—C2—N1176.19 (12)C3—N1—C2—C177.57 (16)
O2—C1—C2—N13.8 (2)C3—N1—C7—C61.3 (2)
O3—C4—C5—C6179.55 (13)C3—C4—C5—C60.3 (2)
N1—C3—C4—O3179.67 (12)C4—C5—C6—C70.3 (2)
N1—C3—C4—C50.47 (19)C5—C6—C7—N10.5 (2)
C2—N1—C3—C4178.92 (12)C7—N1—C2—C1100.12 (15)
C2—N1—C7—C6178.87 (12)C7—N1—C3—C41.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O2i0.86 (2)1.87 (2)2.704 (2)164 (2)
O1W—H1W2···O1ii0.87 (2)2.18 (2)2.9147 (18)143 (2)
O1W—H1W2···O2ii0.87 (2)2.41 (2)3.239 (2)159 (2)
O2W—H2W1···O1Wiii0.86 (2)1.87 (2)2.725 (2)178 (2)
O2W—H2W2···O1iv0.86 (2)1.94 (3)2.785 (2)168 (2)
O3—H8···O2W0.86 (1)1.72 (2)2.5764 (19)177 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z1; (iii) x, y+1, z; (iv) x, y+1, z1.
 

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