N-(2-Aza-niumyleth-yl)carbamate monohydrate.

In the crystal structure of the title compound, C(3)H(8)N(2)O(2)·H(2)O, the organic mol-ecule exists as zwitterion with the carboxyl group deprotonated and the amino group protonated. In the crystal, the components are linked by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

CO2 readily reacts with amines to yied carbamates, see: Brown & Gray (1982 ▶); Dell’Amico et al. (2003) ▶; Jing et al. (2007 ▶). For N-(2-ammonio­eth­yl)carbamate (AECM), a reactive product of ethyl­enediamine with CO2, see: Garbauskas et al. (1983 ▶); Antsyshkina et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C3H8N2O2·H2O

M = 122.13

Monoclinic,

a = 8.0301 (6) Å

b = 8.7842 (7) Å

c = 8.1748 (6) Å

β = 98.889 (1)°

V = 569.71 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.35 × 0.34 × 0.30 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.945, T max = 0.966

2877 measured reflections

1002 independent reflections

960 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.04

1002 reflections

82 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044850/nc2244sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044850/nc2244Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044850/nc2244Isup3.cml

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

C3H8N2O2·H2O	F(000) = 264.0
Mr = 122.13	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Melting point: 358 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.0301 (6) Å	Cell parameters from 1358 reflections
b = 8.7842 (7) Å	θ = 2.4–18.3°
c = 8.1748 (6) Å	µ = 0.12 mm−1
β = 98.889 (1)°	T = 293 K
V = 569.71 (7) Å3	Block, colorless
Z = 4	0.35 × 0.34 × 0.30 mm

Bruker APEX area-detector diffractometer	1002 independent reflections
Radiation source: fine-focus sealed tube	960 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scan	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.945, Tmax = 0.966	k = −10→10
2877 measured reflections	l = −9→6

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.1863P] where P = (Fo2 + 2Fc2)/3
1002 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
O3	0.79493 (17)	0.47441 (13)	0.42240 (14)	0.0480 (4)
H3A	0.788 (2)	0.472 (2)	0.326 (3)	0.050 (5)*
H3B	0.844 (3)	0.391 (3)	0.466 (3)	0.069 (6)*
O2	0.91742 (12)	0.29983 (10)	0.06003 (11)	0.0324 (3)
O1	0.75733 (13)	0.50450 (10)	0.08899 (11)	0.0325 (3)
N1	0.82463 (13)	0.69023 (12)	−0.32825 (13)	0.0270 (3)
H1D	0.9110	0.6736	−0.2480	0.041*
H1E	0.8288	0.7855	−0.3644	0.041*
H1C	0.8303	0.6260	−0.4114	0.041*
N2	0.76650 (14)	0.40847 (12)	−0.16430 (13)	0.0265 (3)
H2	0.8216	0.3547	−0.2257	0.032*
C3	0.81591 (15)	0.40494 (13)	0.00256 (15)	0.0235 (3)
C2	0.62537 (16)	0.49851 (15)	−0.24347 (16)	0.0280 (3)
H2A	0.5340	0.4898	−0.1790	0.034*
H2B	0.5862	0.4560	−0.3521	0.034*
C1	0.66425 (16)	0.66607 (15)	−0.26316 (16)	0.0288 (3)
H1A	0.5729	0.7126	−0.3380	0.035*
H1B	0.6709	0.7161	−0.1566	0.035*

	U11	U22	U33	U12	U13	U23
O3	0.0844 (9)	0.0333 (6)	0.0250 (6)	0.0148 (6)	0.0046 (6)	−0.0027 (5)
O2	0.0397 (5)	0.0250 (5)	0.0294 (5)	0.0052 (4)	−0.0050 (4)	0.0000 (4)
O1	0.0459 (6)	0.0274 (5)	0.0252 (5)	0.0038 (4)	0.0084 (4)	−0.0035 (4)
N1	0.0343 (6)	0.0222 (5)	0.0239 (5)	−0.0015 (4)	0.0022 (4)	0.0029 (4)
N2	0.0349 (6)	0.0236 (6)	0.0213 (6)	0.0056 (4)	0.0050 (4)	0.0001 (4)
C3	0.0279 (6)	0.0183 (6)	0.0243 (6)	−0.0041 (5)	0.0044 (5)	0.0003 (5)
C2	0.0273 (6)	0.0297 (7)	0.0263 (7)	−0.0017 (5)	0.0018 (5)	0.0038 (5)
C1	0.0316 (7)	0.0263 (7)	0.0283 (7)	0.0062 (5)	0.0036 (5)	0.0023 (5)

O3—H3A	0.78 (2)	N2—C3	1.3608 (16)
O3—H3B	0.88 (3)	N2—C2	1.4499 (16)
O2—C3	1.2725 (15)	N2—H2	0.8600
O1—C3	1.2603 (15)	C2—C1	1.5184 (18)
N1—C1	1.4828 (16)	C2—H2A	0.9700
N1—H1D	0.8900	C2—H2B	0.9700
N1—H1E	0.8900	C1—H1A	0.9700
N1—H1C	0.8900	C1—H1B	0.9700
H3A—O3—H3B	110 (2)	N2—C2—C1	114.63 (10)
C1—N1—H1D	109.5	N2—C2—H2A	108.6
C1—N1—H1E	109.5	C1—C2—H2A	108.6
H1D—N1—H1E	109.5	N2—C2—H2B	108.6
C1—N1—H1C	109.5	C1—C2—H2B	108.6
H1D—N1—H1C	109.5	H2A—C2—H2B	107.6
H1E—N1—H1C	109.5	N1—C1—C2	112.39 (10)
C3—N2—C2	123.13 (10)	N1—C1—H1A	109.1
C3—N2—H2	118.4	C2—C1—H1A	109.1
C2—N2—H2	118.4	N1—C1—H1B	109.1
O1—C3—O2	124.74 (11)	C2—C1—H1B	109.1
O1—C3—N2	118.03 (11)	H1A—C1—H1B	107.9
O2—C3—N2	117.23 (11)
C2—N2—C3—O1	−13.44 (17)	C3—N2—C2—C1	79.98 (15)
C2—N2—C3—O2	165.99 (11)	N2—C2—C1—N1	46.09 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1	0.80 (3)	1.92 (3)	2.708 (2)	170 (3)
O3—H3B···O2i	0.86 (3)	1.92 (3)	2.773 (2)	171 (3)
N1—H1C···O3ii	0.89	1.89	2.767 (2)	167.
N1—H1D···O2iii	0.89	1.91	2.775 (2)	163.
N1—H1E···O1iv	0.89	1.95	2.798 (2)	158.
N2—H2···O2v	0.86	2.43	3.278 (2)	167.
C2—H2A···O1vi	0.97	2.56	3.499 (2)	163.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1	0.80 (3)	1.92 (3)	2.708 (2)	170 (3)
O3—H3B⋯O2i	0.86 (3)	1.92 (3)	2.773 (2)	171 (3)
N1—H1C⋯O3ii	0.89	1.89	2.767 (2)	167
N1—H1D⋯O2iii	0.89	1.91	2.775 (2)	163
N1—H1E⋯O1iv	0.89	1.95	2.798 (2)	158
N2—H2⋯O2v	0.86	2.43	3.278 (2)	167
C2—H2A⋯O1vi	0.97	2.56	3.499 (2)	163

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