3-Hydroxy­pyridinium-1-acetate monohydrate

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C5      ..       2.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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

Crystal data

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) Å^3	Sheet, colorless
Z = 8	0.39 × 0.26 × 0.15 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 0.3906P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2^i	0.86 (1)	1.86 (1)	2.6934 (14)	165 (2)
O1W—H1W2···O1^ii	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.