l-Serine methyl ester hydro-chloride.

In the enanti-opure crystal of the title compound, C(4)H(10)NO(3) (+)·Cl(-), inter-molecular O-H⋯Cl and N-H⋯Cl hydrogen bonds link the mol-ecules into layers parallel to (001).

Related literature

Esterification of the carboxyl group of amino acids plays an important role in the synthesis of peptides, especially due to the increased solubility in non-aquous organic solvents, see: Bodanszky (1993 ▶). For related structures, see: Bryndal et al. (2006 ▶); Görbitz (1989 ▶). For the determination of the absolute structure, see: Flack & Bernardinelli (2000 ▶); Flack & Shmueli (2007 ▶); Hooft et al. (2008 ▶).

Experimental

Crystal data

C4H10NO3 +·Cl−

M = 155.58

Monoclinic,

a = 5.22645 (9) Å

b = 6.39388 (14) Å

c = 11.6420 (4) Å

β = 90.090 (1)°

V = 389.04 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 150 K

0.38 × 0.33 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.78, T max = 0.93

15456 measured reflections

3449 independent reflections

3242 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.058

S = 1.07

3449 reflections

100 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1599 Friedel pairs

Flack parameter: 0.00 (3)

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: PEAKREF (Schreurs, 2005 ▶); data reduction: EVAL15 (Xian et al., 2006 ▶) and SADABS (Sheldrick, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046480/vm2012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046480/vm2012Isup2.hkl

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

C4H10NO3+·Cl−	F(000) = 164
Mr = 155.58	Dx = 1.328 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 14244 reflections
a = 5.22645 (9) Å	θ = 1.8–35.0°
b = 6.39388 (14) Å	µ = 0.44 mm−1
c = 11.6420 (4) Å	T = 150 K
β = 90.090 (1)°	Irregular plate, colourless
V = 389.04 (2) Å3	0.38 × 0.33 × 0.15 mm
Z = 2

Nonius KappaCCD diffractometer	3449 independent reflections
Radiation source: rotating anode	3242 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 35.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→8
Tmin = 0.78, Tmax = 0.93	k = −10→10
15456 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058	w = 1/[σ2(Fo2) + (0.0329P)2 + 0.0147P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.002
3449 reflections	Δρmax = 0.25 e Å−3
100 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 1600 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (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	0.19488 (14)	0.39944 (12)	0.93010 (6)	0.03194 (14)
O2	0.32242 (18)	0.69384 (13)	0.84254 (7)	0.04120 (18)
O3	0.57878 (12)	0.22667 (10)	0.72179 (7)	0.02923 (13)
H3	0.644 (3)	0.119 (3)	0.6913 (14)	0.045 (4)*
N1	0.25944 (14)	0.54258 (11)	0.63222 (7)	0.02279 (12)
H1A	0.411 (3)	0.597 (3)	0.6391 (12)	0.037 (4)*
H1B	0.254 (3)	0.473 (3)	0.5725 (15)	0.045 (4)*
H1C	0.149 (2)	0.643 (2)	0.6261 (11)	0.029 (3)*
C1	0.24364 (16)	0.51767 (14)	0.83958 (7)	0.02379 (14)
C2	0.18095 (14)	0.40362 (12)	0.72813 (7)	0.02175 (13)
H2	−0.0084	0.3827	0.7239	0.026*
C3	0.31005 (16)	0.19224 (13)	0.71800 (8)	0.02470 (14)
H3A	0.2571	0.1003	0.7821	0.030*
H3B	0.2616	0.1242	0.6447	0.030*
C4	0.2501 (2)	0.49492 (19)	1.04131 (9)	0.0378 (2)
H4A	0.4322	0.5307	1.0456	0.057*
H4B	0.2079	0.3961	1.1028	0.057*
H4C	0.1473	0.6220	1.0502	0.057*
Cl1	0.77391 (3)	0.81723 (3)	0.608559 (15)	0.02488 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0416 (3)	0.0290 (3)	0.0252 (3)	−0.0042 (3)	0.0023 (2)	0.0007 (2)
O2	0.0668 (5)	0.0250 (3)	0.0317 (3)	−0.0129 (4)	−0.0020 (3)	−0.0044 (3)
O3	0.0229 (3)	0.0219 (3)	0.0429 (4)	0.0033 (2)	−0.0034 (2)	−0.0061 (2)
N1	0.0220 (3)	0.0201 (3)	0.0263 (3)	0.0021 (2)	−0.0026 (2)	−0.0013 (2)
C1	0.0236 (3)	0.0218 (3)	0.0260 (3)	0.0014 (3)	0.0001 (3)	−0.0023 (3)
C2	0.0187 (3)	0.0196 (3)	0.0270 (3)	−0.0016 (3)	−0.0014 (2)	−0.0012 (3)
C3	0.0250 (3)	0.0168 (3)	0.0323 (4)	−0.0016 (3)	−0.0027 (3)	−0.0025 (3)
C4	0.0485 (6)	0.0403 (5)	0.0248 (4)	0.0096 (4)	0.0003 (4)	−0.0030 (4)
Cl1	0.02321 (7)	0.02180 (7)	0.02965 (8)	0.00378 (7)	0.00166 (5)	0.00182 (8)

O1—C1	1.3221 (11)	C1—C2	1.5235 (12)
O1—C4	1.4598 (13)	C2—C3	1.5153 (12)
O2—C1	1.1998 (11)	C2—H2	1.0000
O3—C3	1.4223 (10)	C3—H3A	0.9900
O3—H3	0.847 (18)	C3—H3B	0.9900
N1—C2	1.4852 (11)	C4—H4A	0.9800
N1—H1A	0.867 (16)	C4—H4B	0.9800
N1—H1B	0.825 (18)	C4—H4C	0.9800
N1—H1C	0.865 (14)
C1—O1—C4	115.45 (8)	C3—C2—H2	108.5
C3—O3—H3	104.9 (11)	C1—C2—H2	108.5
C2—N1—H1A	115.1 (10)	O3—C3—C2	107.42 (6)
C2—N1—H1B	107.6 (12)	O3—C3—H3A	110.2
H1A—N1—H1B	108.9 (14)	C2—C3—H3A	110.2
C2—N1—H1C	108.6 (9)	O3—C3—H3B	110.2
H1A—N1—H1C	108.6 (14)	C2—C3—H3B	110.2
H1B—N1—H1C	107.7 (14)	H3A—C3—H3B	108.5
O2—C1—O1	125.48 (9)	O1—C4—H4A	109.5
O2—C1—C2	123.17 (8)	O1—C4—H4B	109.5
O1—C1—C2	111.33 (7)	H4A—C4—H4B	109.5
N1—C2—C3	110.58 (7)	O1—C4—H4C	109.5
N1—C2—C1	107.14 (6)	H4A—C4—H4C	109.5
C3—C2—C1	113.45 (7)	H4B—C4—H4C	109.5
N1—C2—H2	108.5
C4—O1—C1—O2	−1.64 (14)	O2—C1—C2—C3	127.65 (10)
C4—O1—C1—C2	179.72 (7)	O1—C1—C2—C3	−53.67 (9)
O2—C1—C2—N1	5.33 (11)	N1—C2—C3—O3	59.87 (9)
O1—C1—C2—N1	−175.99 (7)	C1—C2—C3—O3	−60.53 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.867 (16)	2.390 (16)	3.2237 (8)	161.2 (14)
N1—H1B···Cl1i	0.825 (18)	2.336 (18)	3.1563 (8)	172.7 (16)
N1—H1C···Cl1ii	0.865 (14)	2.264 (14)	3.0979 (7)	161.9 (12)
O3—H3···Cl1iii	0.847 (18)	2.261 (18)	3.1041 (7)	173.9 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.867 (16)	2.390 (16)	3.2237 (8)	161.2 (14)
N1—H1B⋯Cl1i	0.825 (18)	2.336 (18)	3.1563 (8)	172.7 (16)
N1—H1C⋯Cl1ii	0.865 (14)	2.264 (14)	3.0979 (7)	161.9 (12)
O3—H3⋯Cl1iii	0.847 (18)	2.261 (18)	3.1041 (7)	173.9 (15)

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