l-Alanine hydrochloride monohydrate.

Colorless crystals of l-alanine hydrochloride monohydrate, C(3)H(8)NO(2) (+)·Cl(-)·H(2)O, were obtained from a powder sample that had been left standing in a refrigerator for a few years. The structure displays several inter-molecular hydrogen bonds: the hydroxyl O atom is involved in a single hydrogen bond to the chloride anion, while the ammonium group forms one hydrogen bond to the chloride anion and two hydrogen bonds to water mol-ecules. An intermolecular bond between the carbonyl O atom and the ammonium group [2.8459 (15) Å] is also found.

Related literature

For the crystal structures of l-alanine and dl-alanine, see: Simpson & Marsh, (1966 ▶); Dunitz & Ryan, (1966 ▶); Lehmann et al. (1972 ▶); Destro et al. (1988 ▶); Donohue, (1950 ▶); Subha Nandhini et al. (2001 ▶). For the crystal structures of d-alanine hydro­chloride and dl-alanine hydro­chloride, see: di Blasio et al. (1977 ▶); Trotter, (1962 ▶). For the preparation of the title compound with respect to 17O-labelling, see: Steinschneider et al. (1981 ▶).

Experimental

Crystal data

C3H8NO2 +·Cl−·H2O

M = 143.57

Orthorhombic,

a = 6.1925 (13) Å

b = 9.929 (2) Å

c = 11.759 (3) Å

V = 723.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 150 (2) K

0.45 × 0.40 × 0.35 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2001 ▶) T min = 0.819, T max = 0.855

5762 measured reflections

1467 independent reflections

1452 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.053

S = 1.11

1467 reflections

84 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 533 Friedel pairs

Flack parameter: 0.02 (6)

Data collection: SMART for WNT/2000 (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008751/hg2382sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008751/hg2382Isup2.hkl

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

C3H8NO2+·Cl–·H2O	F000 = 304
Mr = 143.57	Dx = 1.319 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 902 reflections
a = 6.1925 (13) Å	θ = 7.4–53.9º
b = 9.929 (2) Å	µ = 0.46 mm−1
c = 11.759 (3) Å	T = 150 (2) K
V = 723.0 (3) Å3	Plate, colourless
Z = 4	0.45 × 0.40 × 0.35 mm

Bruker SMART APEX CCD area-detector diffractometer	1467 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 293(2) K	θmax = 27.0º
ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker 2001)	h = −7→7
Tmin = 0.819, Tmax = 0.855	k = −11→12
5762 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.019	w = 1/[σ2(Fo2) + (0.0308P)2 + 0.0901P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.053	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.19 e Å−3
1467 reflections	Δρmin = −0.20 e Å−3
84 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 533 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (6)

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
Cl	0.19971 (4)	0.55991 (3)	1.25180 (2)	0.02475 (10)
C1	0.8057 (2)	0.60202 (13)	0.88317 (11)	0.0295 (3)
H1A	0.9301	0.6167	0.8360	0.044*
H1B	0.7483	0.6872	0.9073	0.044*
H1C	0.6979	0.5540	0.8407	0.044*
C2	0.6780 (2)	0.49201 (12)	1.06398 (10)	0.0249 (2)
N	0.96092 (17)	0.38728 (10)	0.95162 (8)	0.0230 (2)
HA	1.0116	0.3443	1.0124	0.034*
HB	1.0676	0.4003	0.9021	0.034*
HC	0.8577	0.3381	0.9193	0.034*
O3	1.13229 (15)	0.26883 (10)	1.15289 (8)	0.0261 (2)
O1	0.60730 (17)	0.38141 (9)	1.08180 (8)	0.0342 (2)
O2	0.60094 (18)	0.60494 (10)	1.10708 (9)	0.0374 (2)
H2	0.4967	0.5880	1.1476	0.056*
C3	0.87031 (18)	0.51981 (12)	0.98686 (10)	0.0228 (2)
H3	0.9801	0.5694	1.0299	0.027*
H4	1.159 (3)	0.335 (2)	1.1930 (16)	0.047 (5)*
H5	1.050 (3)	0.2271 (18)	1.1882 (14)	0.036 (5)*

	U11	U22	U33	U12	U13	U23
Cl	0.02114 (14)	0.02522 (15)	0.02790 (15)	0.00128 (9)	0.00012 (12)	−0.00516 (12)
C1	0.0308 (6)	0.0239 (6)	0.0337 (6)	0.0021 (5)	0.0026 (5)	0.0073 (5)
C2	0.0260 (5)	0.0230 (5)	0.0256 (5)	0.0013 (5)	0.0015 (5)	−0.0018 (5)
N	0.0232 (5)	0.0200 (5)	0.0257 (5)	0.0019 (4)	0.0028 (4)	0.0023 (4)
O3	0.0281 (5)	0.0235 (4)	0.0268 (5)	−0.0044 (4)	0.0023 (4)	−0.0008 (4)
O1	0.0398 (5)	0.0238 (4)	0.0389 (5)	−0.0059 (4)	0.0160 (4)	−0.0029 (4)
O2	0.0384 (5)	0.0244 (4)	0.0494 (6)	0.0011 (4)	0.0183 (5)	−0.0046 (4)
C3	0.0227 (5)	0.0183 (5)	0.0274 (6)	−0.0003 (4)	0.0011 (5)	−0.0002 (4)

C1—C3	1.5209 (17)	N—HA	0.8900
C1—H1A	0.9600	N—HB	0.8900
C1—H1B	0.9600	N—HC	0.8900
C1—H1C	0.9600	O3—H4	0.82 (2)
C2—O1	1.2006 (16)	O3—H5	0.78 (2)
C2—O2	1.3196 (15)	O2—H2	0.8200
C2—C3	1.5223 (16)	C3—H3	0.9800
N—C3	1.4893 (15)
C3—C1—H1A	109.5	C3—N—HC	109.5
C3—C1—H1B	109.5	HA—N—HC	109.5
H1A—C1—H1B	109.5	HB—N—HC	109.5
C3—C1—H1C	109.5	H4—O3—H5	104.4 (17)
H1A—C1—H1C	109.5	C2—O2—H2	109.5
H1B—C1—H1C	109.5	N—C3—C1	110.50 (10)
O1—C2—O2	125.34 (11)	N—C3—C2	107.48 (9)
O1—C2—C3	123.71 (11)	C1—C3—C2	111.65 (11)
O2—C2—C3	110.95 (10)	N—C3—H3	109.1
C3—N—HA	109.5	C1—C3—H3	109.1
C3—N—HB	109.5	C2—C3—H3	109.1
HA—N—HB	109.5
O1—C2—C3—N	−6.06 (18)	O1—C2—C3—C1	115.28 (14)
O2—C2—C3—N	174.26 (9)	O2—C2—C3—C1	−64.39 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N—HA···O3	0.89	1.96	2.8479 (14)	174
N—HB···Cli	0.89	2.31	3.1957 (11)	171
N—HC···O3ii	0.89	1.95	2.8380 (15)	180
O2—H2···Cl	0.82	2.23	3.0446 (11)	175
O3—H4···Cliii	0.82 (2)	2.35 (2)	3.1432 (12)	161.0 (17)
O3—H5···Cliv	0.78 (2)	2.38 (2)	3.1283 (11)	163.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—HA⋯O3	0.89	1.96	2.8479 (14)	174
N—HB⋯Cli	0.89	2.31	3.1957 (11)	171
N—HC⋯O3ii	0.89	1.95	2.8380 (15)	180
O2—H2⋯Cl	0.82	2.23	3.0446 (11)	175
O3—H4⋯Cliii	0.82 (2)	2.35 (2)	3.1432 (12)	161.0 (17)
O3—H5⋯Cliv	0.78 (2)	2.38 (2)	3.1283 (11)	163.3 (16)

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