l-Alanine methyl ester hydro-chloride monohydrate.

The enanti-opure title compound, C(4)H(10)NO(2) (+)·Cl(-)·H(2)O, forms a two-dimensional network by inter-molecular hydrogen bonding parallel to (010). Non-merohedral twinning with a twofold rotation about the reciprocal c* axis as twin operation was taken into account during intensity integration and structure refinement. This twinning leads to alternative orientations of the stacked hydrogen-bonded layers.

Related literature

For the related l-serine methyl ester hydro­chloride, see: Schouten & Lutz (2009 ▶). For the theory of twin formation, see: Cahn (1954 ▶). Twin integration is based on Schreurs et al. (2010 ▶) and the twin refinement on Herbst-Irmer & Sheldrick (2002 ▶). The methods of Flack (1983 ▶) and Hooft et al. (2008 ▶) were used for the absolute structure determination.

Experimental

Crystal data

C4H10NO2 +·Cl−·H2O

M = 157.60

Triclinic,

a = 4.9461 (4) Å

b = 6.0134 (4) Å

c = 6.6853 (5) Å

α = 101.833 (4)°

β = 93.533 (3)°

γ = 92.112 (4)°

V = 194.00 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.44 mm−1

T = 110 K

0.39 × 0.29 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (TWINABS-2008/4; Sheldrick, 2008a ▶) T min = 0.69, T max = 0.75

11388 measured reflections

3213 independent reflections

3180 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.015

wR(F 2) = 0.043

S = 1.05

3213 reflections

133 parameters

3 restraints

All H-atom parameters refined

Δρmax = 0.20 e Å−3

Δρmin = −0.13 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: PEAKREF (Schreurs, 2008 ▶); data reduction: Eval15 (Schreurs et al., 2010 ▶) and TWINABS-2008/4 (Sheldrick, 2008a ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: manual editing of SHELXL CIF file.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100420X/ez2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100420X/ez2229Isup2.hkl

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

C4H10NO2+·Cl−·H2O	Z = 1
Mr = 157.60	F(000) = 84
Triclinic, P1	Dx = 1.349 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9461 (4) Å	Cell parameters from 5169 reflections
b = 6.0134 (4) Å	θ = 3.5–27.5°
c = 6.6853 (5) Å	µ = 0.44 mm−1
α = 101.833 (4)°	T = 110 K
β = 93.533 (3)°	Plate, colourless
γ = 92.112 (4)°	0.39 × 0.29 × 0.12 mm
V = 194.00 (2) Å3

Nonius KappaCCD diffractometer	3213 independent reflections
Radiation source: rotating anode	3180 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 27.7°, θmin = 3.1°
Absorption correction: multi-scan (TWINABS-2008/4; Sheldrick, 2008a)	h = −6→6
Tmin = 0.69, Tmax = 0.75	k = −7→7
11388 measured reflections	l = −8→8

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)] = 0.015	Hydrogen site location: difference Fourier map
wR(F2) = 0.043	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.0041P] where P = (Fo2 + 2Fc2)/3
3213 reflections	(Δ/σ)max = 0.005
133 parameters	Δρmax = 0.20 e Å−3
3 restraints	Δρmin = −0.13 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
O1	0.52552 (12)	0.30665 (9)	0.60201 (9)	0.01877 (12)
O2	0.74232 (12)	0.64013 (9)	0.59202 (9)	0.01863 (12)
N1	0.29086 (13)	0.79507 (11)	0.43187 (9)	0.01456 (12)
H1N	0.447 (2)	0.8444 (16)	0.3859 (16)	0.018 (2)*
H2N	0.143 (2)	0.8271 (19)	0.3614 (17)	0.021 (3)*
H3N	0.284 (2)	0.8560 (18)	0.5673 (18)	0.021 (2)*
C1	0.54988 (14)	0.50654 (11)	0.54561 (10)	0.01343 (14)
C2	0.30541 (15)	0.54425 (12)	0.41118 (12)	0.01473 (14)
H2	0.150 (2)	0.4952 (16)	0.4556 (15)	0.016 (2)*
C3	0.3288 (2)	0.42892 (16)	0.18812 (15)	0.02366 (18)
H3A	0.171 (3)	0.452 (2)	0.110 (2)	0.047 (4)*
H3B	0.494 (4)	0.489 (3)	0.146 (3)	0.060 (5)*
H3C	0.331 (2)	0.273 (2)	0.1796 (19)	0.031 (3)*
C4	0.75776 (19)	0.25176 (15)	0.72382 (14)	0.02231 (18)
H4A	0.909 (3)	0.225 (2)	0.644 (2)	0.040 (3)*
H4B	0.695 (4)	0.118 (3)	0.779 (3)	0.064 (4)*
H4C	0.819 (4)	0.360 (3)	0.821 (3)	0.052 (4)*
Cl1	0.793162 (15)	0.934964 (15)	0.171315 (15)	0.01891 (5)
O3	0.26844 (13)	0.86392 (12)	0.85023 (9)	0.02491 (13)
H1O	0.415 (4)	0.880 (3)	0.930 (3)	0.057 (5)*
H2O	0.133 (3)	0.878 (2)	0.912 (2)	0.044 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0167 (3)	0.0218 (3)	0.0201 (3)	−0.0007 (2)	−0.0021 (2)	0.0111 (2)
O2	0.0107 (3)	0.0205 (3)	0.0253 (3)	0.0016 (2)	−0.0013 (2)	0.0067 (2)
N1	0.0123 (3)	0.0188 (3)	0.0132 (3)	0.0052 (2)	0.0008 (2)	0.0038 (2)
C1	0.0107 (4)	0.0182 (3)	0.0123 (3)	0.0038 (3)	0.0042 (3)	0.0038 (3)
C2	0.0098 (3)	0.0180 (3)	0.0176 (3)	0.0008 (2)	0.0007 (3)	0.0066 (3)
C3	0.0296 (6)	0.0195 (3)	0.0186 (4)	0.0036 (3)	−0.0074 (4)	−0.0013 (3)
C4	0.0195 (4)	0.0277 (4)	0.0231 (4)	0.0026 (3)	−0.0034 (4)	0.0143 (3)
Cl1	0.01091 (8)	0.03258 (8)	0.01630 (8)	0.00378 (5)	0.00140 (5)	0.01156 (6)
O3	0.0129 (3)	0.0475 (4)	0.0132 (3)	0.0008 (3)	0.0011 (2)	0.0038 (2)

O1—C1	1.3351 (8)	C2—H2	0.901 (11)
O1—C4	1.4541 (10)	C3—H3A	0.939 (14)
O2—C1	1.2052 (9)	C3—H3B	0.961 (18)
N1—C2	1.4909 (9)	C3—H3C	0.930 (12)
N1—H1N	0.909 (11)	C4—H4A	0.947 (14)
N1—H2N	0.895 (12)	C4—H4B	1.001 (17)
N1—H3N	0.908 (12)	C4—H4C	0.854 (18)
C1—C2	1.5137 (10)	O3—H1O	0.860 (18)
C2—C3	1.5236 (12)	O3—H2O	0.808 (17)
C1—O1—C4	115.00 (6)	C3—C2—H2	109.9 (6)
C2—N1—H1N	106.5 (6)	C2—C3—H3A	109.1 (9)
C2—N1—H2N	110.3 (7)	C2—C3—H3B	107.1 (10)
H1N—N1—H2N	112.5 (10)	H3A—C3—H3B	114.5 (13)
C2—N1—H3N	107.0 (7)	C2—C3—H3C	108.4 (8)
H1N—N1—H3N	110.0 (10)	H3A—C3—H3C	105.7 (11)
H2N—N1—H3N	110.2 (10)	H3B—C3—H3C	111.9 (12)
O2—C1—O1	125.01 (7)	O1—C4—H4A	110.8 (9)
O2—C1—C2	123.63 (6)	O1—C4—H4B	105.5 (10)
O1—C1—C2	111.36 (6)	H4A—C4—H4B	113.8 (13)
N1—C2—C1	106.75 (6)	O1—C4—H4C	114.3 (11)
N1—C2—C3	110.50 (6)	H4A—C4—H4C	102.3 (14)
C1—C2—C3	111.57 (6)	H4B—C4—H4C	110.4 (15)
N1—C2—H2	106.5 (6)	H1O—O3—H2O	112.9 (15)
C1—C2—H2	111.5 (6)
C4—O1—C1—O2	−1.75 (11)	O1—C1—C2—N1	155.83 (6)
C4—O1—C1—C2	177.22 (6)	O2—C1—C2—C3	95.64 (9)
O2—C1—C2—N1	−25.18 (9)	O1—C1—C2—C3	−83.35 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1	0.909 (11)	2.418 (11)	3.3007 (7)	163.9 (9)
N1—H2N···Cl1i	0.895 (12)	2.275 (12)	3.1665 (6)	174.2 (10)
N1—H3N···O3	0.908 (12)	1.888 (12)	2.7519 (9)	158.2 (9)
O3—H1O···Cl1ii	0.860 (18)	2.364 (18)	3.2220 (7)	175.1 (15)
O3—H2O···Cl1iii	0.808 (17)	2.470 (17)	3.2613 (7)	166.9 (14)
C2—H2···O2i	0.901 (11)	2.385 (10)	3.1302 (9)	140.0 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1	0.909 (11)	2.418 (11)	3.3007 (7)	163.9 (9)
N1—H2N⋯Cl1i	0.895 (12)	2.275 (12)	3.1665 (6)	174.2 (10)
N1—H3N⋯O3	0.908 (12)	1.888 (12)	2.7519 (9)	158.2 (9)
O3—H1O⋯Cl1ii	0.860 (18)	2.364 (18)	3.2220 (7)	175.1 (15)
O3—H2O⋯Cl1iii	0.808 (17)	2.470 (17)	3.2613 (7)	166.9 (14)
C2—H2⋯O2i	0.901 (11)	2.385 (10)	3.1302 (9)	140.0 (8)

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