Glycine ethyl ester hydro-chloride.

In the crystal structure of the title compound, C(4)H(10)NO(2) (+)·Cl(-) (systematic name: 3-eth-oxy-3-oxopropan-1-aminium chlor-ide), there are strong inter-molecular N-H⋯Cl, C-H⋯Cl and C-H⋯O hydrogen-bonding inter-actions between the free chloride anion and the organic cation, resulting in a two-dimensional supra-molecular network in the ab plane.

Related literature

The title compound is an inter­mediate in the synthesis of dichloro­vinyl­cyclo­propane carb­oxy­lic acid, see: Xue (1995 ▶). For related structures, see: Taubald et al. (1984 ▶); Gainsford et al. (1986 ▶); Eduok et al. (1994 ▶).

Experimental

Crystal data

C4H10NO2 +·Cl−

M = 139.58

Monoclinic,

a = 8.965 (3) Å

b = 12.543 (4) Å

c = 5.972 (2) Å

β = 103.630 (5)°

V = 652.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.50 mm−1

T = 123 K

0.33 × 0.33 × 0.23 mm

Data collection

Rigaku SPIDER diffractometer

4996 measured reflections

1489 independent reflections

1294 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.064

S = 1.00

1489 reflections

87 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.21 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028849/bv2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028849/bv2143Isup2.hkl

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

C4H10NO2+·Cl−	F(000) = 296
Mr = 139.58	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Melting point: 145(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.965 (3) Å	Cell parameters from 1964 reflections
b = 12.543 (4) Å	θ = 3.3–27.5°
c = 5.972 (2) Å	µ = 0.50 mm−1
β = 103.630 (5)°	T = 123 K
V = 652.6 (4) Å3	Block, colorless
Z = 4	0.33 × 0.33 × 0.23 mm

Rigaku SPIDER diffractometer	1294 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.024
graphite	θmax = 27.5°, θmin = 3.3°
ω scans	h = −10→11
4996 measured reflections	k = −16→11
1489 independent reflections	l = −7→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.031P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1489 reflections	Δρmax = 0.40 e Å−3
87 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	−0.00205 (3)	0.38254 (2)	0.24012 (5)	0.01640 (11)
O1	0.52878 (10)	0.38513 (7)	0.85715 (16)	0.0168 (2)
O2	0.34886 (10)	0.29775 (7)	0.59414 (15)	0.0171 (2)
N1	0.11868 (13)	0.36318 (9)	0.7845 (2)	0.0144 (2)
C2	0.38589 (14)	0.35635 (9)	0.7575 (2)	0.0132 (3)
C1	0.27318 (14)	0.40847 (10)	0.8745 (2)	0.0136 (3)
H1A	0.3056	0.3965	1.0429	0.016*
H1B	0.2709	0.4863	0.8461	0.016*
C3	0.64973 (15)	0.34018 (11)	0.7579 (2)	0.0184 (3)
H3A	0.6205	0.2672	0.7010	0.022*
H3B	0.7464	0.3354	0.8786	0.022*
C4	0.67496 (16)	0.40810 (11)	0.5624 (2)	0.0222 (3)
H4A	0.5809	0.4096	0.4392	0.027*
H4B	0.7589	0.3782	0.5029	0.027*
H4C	0.7015	0.4808	0.6179	0.027*
H0A	0.0807 (19)	0.3806 (11)	0.635 (3)	0.022 (4)*
H0B	0.054 (2)	0.3873 (13)	0.869 (3)	0.035 (5)*
H0C	0.1184 (19)	0.2925 (15)	0.797 (3)	0.033 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01827 (17)	0.01928 (19)	0.01196 (16)	0.00511 (12)	0.00419 (11)	0.00078 (11)
O1	0.0131 (4)	0.0206 (5)	0.0171 (5)	−0.0019 (4)	0.0045 (4)	−0.0039 (4)
O2	0.0163 (4)	0.0191 (5)	0.0157 (5)	−0.0003 (4)	0.0033 (4)	−0.0049 (4)
N1	0.0149 (5)	0.0166 (6)	0.0128 (5)	−0.0010 (4)	0.0055 (4)	−0.0022 (4)
C2	0.0150 (6)	0.0120 (6)	0.0131 (6)	−0.0006 (5)	0.0043 (5)	0.0027 (4)
C1	0.0136 (6)	0.0132 (6)	0.0141 (6)	−0.0010 (5)	0.0038 (5)	−0.0020 (5)
C3	0.0130 (6)	0.0224 (7)	0.0202 (7)	0.0013 (5)	0.0046 (5)	−0.0017 (5)
C4	0.0216 (7)	0.0228 (7)	0.0252 (7)	−0.0032 (5)	0.0115 (6)	−0.0029 (6)

O1—C2	1.3290 (15)	C1—H1A	0.9900
O1—C3	1.4654 (16)	C1—H1B	0.9900
O2—C2	1.2040 (15)	C3—C4	1.505 (2)
N1—C1	1.4762 (16)	C3—H3A	0.9900
N1—H0A	0.902 (17)	C3—H3B	0.9900
N1—H0B	0.906 (19)	C4—H4A	0.9800
N1—H0C	0.890 (18)	C4—H4B	0.9800
C2—C1	1.5065 (18)	C4—H4C	0.9800
C2—O1—C3	116.20 (10)	C2—C1—H1B	109.7
C1—N1—H0A	111.7 (10)	H1A—C1—H1B	108.2
C1—N1—H0B	109.8 (12)	O1—C3—C4	110.89 (11)
H0A—N1—H0B	109.0 (16)	O1—C3—H3A	109.5
C1—N1—H0C	111.9 (11)	C4—C3—H3A	109.5
H0A—N1—H0C	108.6 (14)	O1—C3—H3B	109.5
H0B—N1—H0C	105.6 (15)	C4—C3—H3B	109.5
O2—C2—O1	125.54 (12)	H3A—C3—H3B	108.0
O2—C2—C1	123.62 (12)	C3—C4—H4A	109.5
O1—C2—C1	110.83 (11)	C3—C4—H4B	109.5
N1—C1—C2	109.79 (10)	H4A—C4—H4B	109.5
N1—C1—H1A	109.7	C3—C4—H4C	109.5
C2—C1—H1A	109.7	H4A—C4—H4C	109.5
N1—C1—H1B	109.7	H4B—C4—H4C	109.5
C3—O1—C2—O2	−0.45 (18)	O1—C2—C1—N1	−171.55 (10)
C3—O1—C2—C1	−179.62 (10)	C2—O1—C3—C4	86.87 (14)
O2—C2—C1—N1	9.27 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H0A···Cl1	0.904 (17)	2.300 (17)	3.1845 (16)	166.1 (12)
N1—H0B···Cl1i	0.906 (18)	2.386 (18)	3.1658 (16)	144.3 (15)
N1—H0C···Cl1ii	0.890 (19)	2.435 (19)	3.2566 (16)	153.7 (15)
C1—H1A···O2ii	0.99	2.47	2.9072 (18)	106
C3—H3B···Cl1iii	0.99	2.79	3.7529 (18)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H0A⋯Cl1	0.904 (17)	2.300 (17)	3.1845 (16)	166.1 (12)
N1—H0B⋯Cl1i	0.906 (18)	2.386 (18)	3.1658 (16)	144.3 (15)
N1—H0C⋯Cl1	0.890 (19)	2.435 (19)	3.2566 (16)	153.7 (15)
C1—H1A⋯O2	0.99	2.47	2.9072 (18)	106
C3—H3B⋯Cl1ii	0.99	2.79	3.7529 (18)	164

Symmetry codes: (i) ; (ii) .