(3-Ammonio-2-hydroxy­prop­yl)carbamate monohydrate

The asymmetric unit of the title compound, C₄H₁₀N₂O₃·H₂O, contains one zwitterionic organic molecule and two half-mol­ecules of water, the O atoms of which lie on a twofold axis. Inter­molecular hydrogen bonds involving the water mol­ecules, the ammonium cationic group and the carboxylate group link the mol­ecules into an extended three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.149
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.

(3-Ammonio-2-hydroxypropyl)carbamate monohydrate

Crystal data

C4H10N2O3·H2O	F(000) = 328
Mr = 152.16	Dx = 1.422 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2364 reflections
a = 8.500 (3) Å	θ = 2.6–26.4°
b = 5.950 (2) Å	µ = 0.13 mm^−1
c = 15.665 (4) Å	T = 298 K
β = 116.204 (15)°	Block, pale yellow
V = 710.8 (4) Å^3	0.36 × 0.16 × 0.11 mm
Z = 4

Data collection

Bruck SMART CCD area-detector diffractometer	1253 independent reflections
Radiation source: fine-focus sealed tube	768 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
Tmin = 0.966, Tmax = 0.986	k = −7→6
3521 measured reflections	l = −18→18

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0638P)^2 + 0.5606P] where P = (Fo^2 + 2Fc^2)/3
1253 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (D₂O, δ, p.p.m.): 3.23 (m, 2H), 3.61 (m, 2H), 4.47 (m, 2H). Elemental analysis, calculated for C₄H₁₀N₂O3: C 35.82, H 7.51, N 20.88%; found: C 35.96, H 7.62, N 20.48%. ESI-MS (–P) m/z = 133.1.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7394 (3)	0.4616 (4)	0.91221 (16)	0.0581 (8)
H1A	0.7134	0.3948	0.8620	0.070*
O2	0.6935 (3)	0.6946 (4)	0.60410 (14)	0.0425 (6)
O3	0.6954 (3)	0.9983 (3)	0.68671 (14)	0.0393 (6)
N1	0.8149 (4)	0.6769 (4)	0.76347 (17)	0.0391 (7)
H1	0.8420	0.5395	0.7593	0.047*
N2	0.6578 (3)	0.7408 (4)	1.03015 (17)	0.0371 (7)
H2A	0.6864	0.8120	1.0850	0.056*
H2B	0.6669	0.5931	1.0402	0.056*
H2C	0.5480	0.7750	0.9896	0.056*
C1	0.8632 (4)	0.7653 (6)	0.8579 (2)	0.0377 (8)
H1B	0.8673	0.9281	0.8560	0.045*
H1C	0.9795	0.7121	0.9006	0.045*
C2	0.7345 (4)	0.6949 (5)	0.8963 (2)	0.0360 (8)
H2	0.6157	0.7375	0.8503	0.043*
C3	0.7777 (4)	0.8112 (6)	0.9896 (2)	0.0402 (8)
H3A	0.8974	0.7762	1.0344	0.048*
H3B	0.7691	0.9725	0.9798	0.048*
C4	0.7313 (4)	0.7922 (5)	0.6819 (2)	0.0309 (7)
O4	0.5000	0.2400 (5)	0.7500	0.0494 (9)
H5	0.5445	0.1692	0.7188	0.059*
O5	1.0000	0.2510 (5)	0.7500	0.0601 (10)
H6	0.9100	0.1685	0.7348	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.095 (2)	0.0408 (16)	0.0434 (14)	−0.0045 (14)	0.0346 (14)	−0.0010 (11)
O2	0.0516 (14)	0.0441 (15)	0.0315 (12)	0.0022 (11)	0.0180 (11)	−0.0060 (10)
O3	0.0527 (14)	0.0294 (13)	0.0389 (13)	0.0069 (10)	0.0231 (11)	0.0026 (10)
N1	0.0542 (17)	0.0315 (15)	0.0332 (15)	0.0093 (13)	0.0209 (13)	0.0036 (12)
N2	0.0516 (17)	0.0304 (15)	0.0296 (13)	−0.0011 (13)	0.0182 (12)	−0.0022 (11)
C1	0.0396 (18)	0.043 (2)	0.0294 (16)	−0.0002 (15)	0.0143 (14)	0.0010 (14)
C2	0.0450 (19)	0.0300 (19)	0.0316 (17)	−0.0027 (14)	0.0156 (15)	−0.0010 (13)
C3	0.046 (2)	0.040 (2)	0.0323 (18)	−0.0090 (15)	0.0154 (16)	−0.0055 (14)
C4	0.0288 (16)	0.0347 (19)	0.0327 (17)	−0.0008 (14)	0.0168 (14)	0.0008 (14)
O4	0.066 (2)	0.0372 (19)	0.062 (2)	0.000	0.0441 (19)	0.000
O5	0.052 (2)	0.0325 (19)	0.089 (3)	0.000	0.025 (2)	0.000

Geometric parameters (Å, º)

O1—C2	1.408 (4)	N2—H2C	0.8900
O1—H1A	0.8204	C1—C2	1.522 (4)
O2—C4	1.257 (3)	C1—H1B	0.9700
O3—C4	1.274 (3)	C1—H1C	0.9700
N1—C4	1.344 (4)	C2—C3	1.508 (4)
N1—C1	1.448 (4)	C2—H2	0.9800
N1—H1	0.8597	C3—H3A	0.9700
N2—C3	1.479 (4)	C3—H3B	0.9700
N2—H2A	0.8900	O4—H5	0.8501
N2—H2B	0.8900	O5—H6	0.8497
C2—O1—H1A	109.5	O1—C2—C3	107.8 (3)
C4—N1—C1	125.3 (3)	O1—C2—C1	111.8 (3)
C4—N1—H1	117.4	C3—C2—C1	110.3 (3)
C1—N1—H1	117.3	O1—C2—H2	109.0
C3—N2—H2A	109.5	C3—C2—H2	109.0
C3—N2—H2B	109.5	C1—C2—H2	109.0
H2A—N2—H2B	109.5	N2—C3—C2	111.6 (3)
C3—N2—H2C	109.5	N2—C3—H3A	109.3
H2A—N2—H2C	109.5	C2—C3—H3A	109.3
H2B—N2—H2C	109.5	N2—C3—H3B	109.3
N1—C1—C2	112.0 (3)	C2—C3—H3B	109.3
N1—C1—H1B	109.2	H3A—C3—H3B	108.0
C2—C1—H1B	109.2	O2—C4—O3	122.5 (3)
N1—C1—H1C	109.2	O2—C4—N1	119.2 (3)
C2—C1—H1C	109.2	O3—C4—N1	118.3 (3)
H1B—C1—H1C	107.9
C4—N1—C1—C2	99.8 (4)	C1—C2—C3—N2	−178.3 (3)
N1—C1—C2—O1	66.5 (3)	C1—N1—C4—O2	−178.5 (3)
N1—C1—C2—C3	−173.6 (3)	C1—N1—C4—O3	2.4 (4)
O1—C2—C3—N2	−56.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O2^i	0.89	1.98	2.805 (3)	153
N2—H2B···O2^ii	0.89	1.95	2.799 (3)	160
N2—H2A···O3^iii	0.89	1.93	2.799 (3)	166
O4—H5···O3^iv	0.85	1.87	2.695 (3)	163
O5—H6···O3^iv	0.85	1.93	2.772 (3)	174
N1—H1···O5	0.86	2.22	3.039 (4)	158
O1—H1A···O4	0.82	2.10	2.787 (3)	141
N2—H2B···O1	0.89	2.47	2.790 (3)	102

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) x, −y+1, z+1/2; (iii) x, −y+2, z+1/2; (iv) x, y−1, z.