4-Carbamoylpiperidinium acetate monohydrate.

In the structure of the title compound, C(6)H(13)N(2)O(+)·C(2)H(3)O(2) (-)·H(2)O, the amide H atoms of the cations form centrosymmetric cyclic hydrogen-bonding associations incorporating two water mol-ecules [graph set R(4) (2)(8)], which are conjoint with cyclic water-bridged amide-amide associations [R(4) (4)(12)] and larger R(4) (4)(20) associations involving the water mol-ecule and the acetate anions, which bridge through the piperidinium H-bond donors, giving an overall three-dimensional framework structure.

Related literature

For structural data on isonipecotamide salts, see: Smith et al. (2010 ▶); Smith & Wermuth (2010a ▶,b ▶). For graph-set motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H13N2O+·C2H3O2 −·H2O

M = 206.24

Triclinic,

a = 5.8219 (2) Å

b = 7.7675 (3) Å

c = 12.4022 (5) Å

α = 81.088 (4)°

β = 78.763 (4)°

γ = 76.202 (4)°

V = 530.75 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.40 × 0.35 × 0.15 mm

Data collection

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.962, T max = 0.980

6385 measured reflections

2087 independent reflections

1602 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.105

S = 0.93

2087 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045538/nk2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045538/nk2071Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H13N2O+·C2H3O2−·H2O	Z = 2
Mr = 206.24	F(000) = 224
Triclinic, P1	Dx = 1.291 Mg m−3
Hall symbol: -P 1	Melting point: 409 K
a = 5.8219 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7675 (3) Å	Cell parameters from 3330 reflections
c = 12.4022 (5) Å	θ = 3.4–28.8°
α = 81.088 (4)°	µ = 0.10 mm−1
β = 78.763 (4)°	T = 200 K
γ = 76.202 (4)°	Plate, colourless
V = 530.75 (4) Å3	0.40 × 0.35 × 0.15 mm

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer	2087 independent reflections
Radiation source: Enhance (Mo) X-ray source	1602 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 16.977 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.962, Tmax = 0.980	l = −15→15
6385 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0733P)2 + 0.0214P] where P = (Fo2 + 2Fc2)/3
2087 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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.

	x	y	z	Uiso*/Ueq
O41A	0.48609 (16)	0.38864 (13)	0.35243 (9)	0.0344 (3)
N1A	0.9204 (2)	0.82745 (15)	0.19803 (10)	0.0274 (4)
N41A	0.7954 (2)	0.21185 (16)	0.42814 (10)	0.0297 (4)
C2A	0.9917 (3)	0.67001 (19)	0.13552 (11)	0.0290 (4)
C3A	0.8415 (2)	0.53343 (18)	0.18703 (11)	0.0264 (4)
C4A	0.8642 (2)	0.47820 (17)	0.30875 (11)	0.0223 (4)
C5A	0.8010 (3)	0.64377 (18)	0.37045 (11)	0.0283 (4)
C6A	0.9525 (3)	0.77742 (19)	0.31557 (12)	0.0319 (5)
C41A	0.6994 (2)	0.35378 (17)	0.36412 (11)	0.0236 (4)
O11	1.43436 (17)	−0.04485 (13)	0.19784 (8)	0.0320 (3)
O12	1.14721 (18)	0.09626 (14)	0.10165 (9)	0.0395 (4)
C1	1.3462 (2)	0.08082 (17)	0.12972 (11)	0.0246 (4)
C2	1.4884 (3)	0.2219 (2)	0.08190 (13)	0.0375 (5)
O1W	1.31002 (18)	0.08400 (15)	0.40367 (9)	0.0314 (3)
H4A	1.03030	0.41690	0.31380	0.0270*
H11A	1.005 (3)	0.917 (2)	0.1664 (15)	0.050 (5)*
H12A	0.757 (3)	0.882 (2)	0.1956 (14)	0.043 (5)*
H21A	1.16000	0.61660	0.13610	0.0350*
H22A	0.96950	0.70700	0.05920	0.0350*
H31A	0.89420	0.42910	0.14720	0.0320*
H32A	0.67480	0.58390	0.18070	0.0320*
H41A	0.958 (3)	0.178 (2)	0.4274 (13)	0.036 (4)*
H42A	0.701 (3)	0.138 (2)	0.4646 (14)	0.045 (5)*
H51A	0.63270	0.69920	0.37160	0.0340*
H52A	0.82710	0.60850	0.44640	0.0340*
H61A	0.90520	0.88300	0.35420	0.0380*
H62A	1.12010	0.72560	0.31940	0.0380*
H21	1.42940	0.28690	0.01690	0.0450*
H22	1.65450	0.16610	0.06270	0.0450*
H23	1.47180	0.30250	0.13570	0.0450*
H11W	1.355 (4)	0.031 (3)	0.3388 (19)	0.069 (7)*
H12W	1.368 (4)	0.175 (3)	0.3891 (17)	0.062 (6)*

	U11	U22	U33	U12	U13	U23
O41A	0.0236 (5)	0.0304 (6)	0.0475 (6)	−0.0104 (4)	−0.0061 (4)	0.0086 (5)
N1A	0.0228 (6)	0.0200 (6)	0.0383 (7)	−0.0088 (5)	−0.0057 (5)	0.0076 (5)
N41A	0.0279 (7)	0.0236 (6)	0.0349 (7)	−0.0100 (5)	−0.0026 (5)	0.0083 (5)
C2A	0.0309 (7)	0.0300 (8)	0.0250 (7)	−0.0108 (6)	−0.0021 (6)	0.0039 (6)
C3A	0.0310 (7)	0.0259 (7)	0.0235 (7)	−0.0116 (6)	−0.0025 (5)	−0.0007 (6)
C4A	0.0192 (6)	0.0198 (6)	0.0269 (7)	−0.0060 (5)	−0.0038 (5)	0.0029 (5)
C5A	0.0345 (8)	0.0271 (7)	0.0247 (7)	−0.0124 (6)	−0.0020 (6)	−0.0016 (6)
C6A	0.0391 (8)	0.0270 (8)	0.0336 (8)	−0.0155 (6)	−0.0057 (6)	−0.0032 (6)
C41A	0.0239 (7)	0.0202 (7)	0.0256 (7)	−0.0065 (5)	−0.0007 (5)	−0.0008 (6)
O11	0.0274 (5)	0.0289 (5)	0.0362 (6)	−0.0050 (4)	−0.0060 (4)	0.0061 (5)
O12	0.0333 (6)	0.0339 (6)	0.0535 (7)	−0.0167 (5)	−0.0175 (5)	0.0165 (5)
C1	0.0250 (7)	0.0227 (7)	0.0257 (7)	−0.0074 (5)	−0.0012 (5)	−0.0015 (6)
C2	0.0368 (8)	0.0335 (8)	0.0450 (9)	−0.0182 (7)	−0.0080 (7)	0.0054 (7)
O1W	0.0325 (6)	0.0304 (6)	0.0324 (6)	−0.0149 (5)	−0.0066 (4)	0.0073 (5)

O41A—C41A	1.2386 (16)	C4A—C41A	1.5186 (18)
O11—C1	1.2667 (16)	C5A—C6A	1.518 (2)
O12—C1	1.2473 (17)	C2A—H21A	0.9700
O1W—H12W	0.84 (2)	C2A—H22A	0.9700
O1W—H11W	0.92 (2)	C3A—H32A	0.9700
N1A—C6A	1.4856 (19)	C3A—H31A	0.9700
N1A—C2A	1.4816 (18)	C4A—H4A	0.9800
N41A—C41A	1.3289 (18)	C5A—H51A	0.9700
N1A—H12A	0.949 (18)	C5A—H52A	0.9700
N1A—H11A	0.940 (17)	C6A—H62A	0.9700
N41A—H41A	0.919 (18)	C6A—H61A	0.9700
N41A—H42A	0.899 (17)	C1—C2	1.509 (2)
C2A—C3A	1.521 (2)	C2—H23	0.9600
C3A—C4A	1.5266 (19)	C2—H21	0.9600
C4A—C5A	1.5311 (19)	C2—H22	0.9600
H11W—O1W—H12W	104 (2)	C2A—C3A—H32A	109.00
C2A—N1A—C6A	111.60 (11)	C4A—C3A—H32A	109.00
H11A—N1A—H12A	104.9 (14)	H31A—C3A—H32A	108.00
C6A—N1A—H11A	109.2 (11)	C4A—C3A—H31A	109.00
C2A—N1A—H11A	112.5 (10)	C5A—C4A—H4A	109.00
C2A—N1A—H12A	109.7 (10)	C41A—C4A—H4A	109.00
C6A—N1A—H12A	108.8 (10)	C3A—C4A—H4A	109.00
C41A—N41A—H42A	118.4 (11)	C4A—C5A—H51A	109.00
C41A—N41A—H41A	121.8 (10)	C6A—C5A—H51A	109.00
H41A—N41A—H42A	119.1 (15)	C6A—C5A—H52A	109.00
N1A—C2A—C3A	110.23 (12)	C4A—C5A—H52A	109.00
C2A—C3A—C4A	110.91 (11)	H51A—C5A—H52A	108.00
C3A—C4A—C41A	111.67 (10)	N1A—C6A—H62A	110.00
C5A—C4A—C41A	108.66 (11)	C5A—C6A—H61A	110.00
C3A—C4A—C5A	109.87 (11)	C5A—C6A—H62A	110.00
C4A—C5A—C6A	111.11 (12)	H61A—C6A—H62A	108.00
N1A—C6A—C5A	109.84 (13)	N1A—C6A—H61A	110.00
O41A—C41A—C4A	120.90 (12)	O11—C1—O12	123.79 (12)
O41A—C41A—N41A	122.94 (12)	O11—C1—C2	117.89 (12)
N41A—C41A—C4A	116.11 (11)	O12—C1—C2	118.31 (12)
N1A—C2A—H21A	110.00	C1—C2—H22	109.00
C3A—C2A—H21A	110.00	C1—C2—H23	109.00
C3A—C2A—H22A	110.00	C1—C2—H21	109.00
H21A—C2A—H22A	108.00	H21—C2—H23	109.00
N1A—C2A—H22A	110.00	H22—C2—H23	109.00
C2A—C3A—H31A	109.00	H21—C2—H22	109.00
C6A—N1A—C2A—C3A	59.57 (16)	C41A—C4A—C5A—C6A	−177.38 (12)
C2A—N1A—C6A—C5A	−59.60 (16)	C3A—C4A—C41A—O41A	−47.52 (17)
N1A—C2A—C3A—C4A	−56.87 (15)	C3A—C4A—C41A—N41A	135.05 (12)
C2A—C3A—C4A—C5A	54.57 (15)	C5A—C4A—C41A—O41A	73.82 (16)
C2A—C3A—C4A—C41A	175.21 (11)	C5A—C4A—C41A—N41A	−103.61 (14)
C3A—C4A—C5A—C6A	−54.94 (16)	C4A—C5A—C6A—N1A	57.10 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H11A···O12i	0.940 (17)	1.793 (17)	2.7311 (16)	175.8 (17)
N1A—H12A···O11ii	0.949 (18)	1.824 (18)	2.7666 (16)	171.8 (14)
N41A—H41A···O1W	0.919 (18)	1.984 (18)	2.8939 (17)	170.2 (15)
N41A—H42A···O1Wiii	0.899 (17)	2.188 (16)	2.9491 (16)	142.1 (15)
O1W—H11W···O11	0.92 (2)	1.87 (2)	2.7871 (15)	172 (2)
O1W—H12W···O41Aiv	0.84 (2)	1.90 (2)	2.7370 (15)	177 (2)
C2A—H22A···O12v	0.97	2.42	3.3428 (18)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H11A⋯O12i	0.940 (17)	1.793 (17)	2.7311 (16)	175.8 (17)
N1A—H12A⋯O11ii	0.949 (18)	1.824 (18)	2.7666 (16)	171.8 (14)
N41A—H41A⋯O1W	0.919 (18)	1.984 (18)	2.8939 (17)	170.2 (15)
N41A—H42A⋯O1Wiii	0.899 (17)	2.188 (16)	2.9491 (16)	142.1 (15)
O1W—H11W⋯O11	0.92 (2)	1.87 (2)	2.7871 (15)	172 (2)
O1W—H12W⋯O41Aiv	0.84 (2)	1.90 (2)	2.7370 (15)	177 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .