Glycine methyl ester hydro-chloride.

THE TITLE COMPOUND [SYSTEMATIC NAME: (methoxy-carbonyl-meth-yl)ammonium chloride], crystallizes as a salt, C(3)H(8)NO(2) (+)·Cl(-), with the charged species inter-acting mutually via strong and highly directional N(+)-H⋯Cl(-) hydrogen bonds which lead to the formation of a supra-molecular tape running parallel to the c axis. Tapes close pack in the solid state mediated by multipoint recognition synthons based on weak C-H⋯O inter-actions and van der Waals contacts between adjacent methyl groups.

Related literature

For related structures, see: Handelsman-Benory et al. (1995 ▶). For detailed background to the role of hydrogen bonds in the supra­molecular organization of organic crystals, see: Nangia & Desiraju (1998 ▶). For general background studies on crystal engineering approaches from our research group, see: Shi et al. (2008 ▶); Paz & Klinowski (2003 ▶); Paz et al. (2002 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C3H8NO2 +·Cl−

M = 125.55

Monoclinic,

a = 8.352 (2) Å

b = 12.505 (3) Å

c = 5.6369 (14) Å

β = 99.730 (9)°

V = 580.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.55 mm−1

T = 150 K

0.08 × 0.02 × 0.02 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.957, T max = 0.989

5189 measured reflections

1539 independent reflections

923 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.184

S = 1.08

1539 reflections

66 parameters

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028414/hg2539sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028414/hg2539Isup2.hkl

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

C3H8NO2+·Cl−	F(000) = 264
Mr = 125.55	Dx = 1.437 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 793 reflections
a = 8.352 (2) Å	θ = 3.0–24.8°
b = 12.505 (3) Å	µ = 0.55 mm−1
c = 5.6369 (14) Å	T = 150 K
β = 99.730 (9)°	Needle, colourless
V = 580.3 (2) Å3	0.08 × 0.02 × 0.02 mm
Z = 4

Bruker X8 Kappa CCD APEXII diffractometer	1539 independent reflections
Radiation source: fine-focus sealed tube	923 reflections with I > 2σ(I)
graphite	Rint = 0.070
φ scans	θmax = 29.1°, θmin = 4.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→11
Tmin = 0.957, Tmax = 0.989	k = −17→16
5189 measured reflections	l = −7→7

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0649P)2 + 1.246P] where P = (Fo2 + 2Fc2)/3
1539 reflections	(Δ/σ)max < 0.001
66 parameters	Δρmax = 1.05 e Å−3
0 restraints	Δρmin = −0.55 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
Cl1	0.47434 (13)	0.11638 (8)	0.24634 (19)	0.0210 (3)
C1	0.7947 (5)	0.0942 (3)	0.8596 (8)	0.0200 (10)
H1D	0.7834	0.0155	0.8502	0.024*
H1E	0.8397	0.1135	1.0280	0.024*
C2	0.9087 (5)	0.1308 (3)	0.6967 (8)	0.0190 (9)
C3	1.1805 (6)	0.1209 (5)	0.6290 (10)	0.0348 (12)
H3A	1.1348	0.1161	0.4573	0.052*
H3B	1.2733	0.0723	0.6660	0.052*
H3C	1.2163	0.1944	0.6682	0.052*
N1	0.6341 (4)	0.1443 (3)	0.7897 (6)	0.0178 (8)
H1A	0.6452	0.2167	0.7915	0.027*
H1B	0.5683	0.1246	0.8954	0.027*
H1C	0.5895	0.1225	0.6390	0.027*
O1	1.0566 (4)	0.0911 (3)	0.7714 (6)	0.0295 (8)
O2	0.8701 (4)	0.1866 (3)	0.5246 (6)	0.0251 (8)

	U11	U22	U33	U12	U13	U23
Cl1	0.0258 (6)	0.0195 (5)	0.0182 (6)	−0.0065 (5)	0.0049 (4)	−0.0014 (5)
C1	0.016 (2)	0.014 (2)	0.030 (3)	−0.0018 (17)	0.0031 (17)	0.0025 (17)
C2	0.021 (2)	0.0111 (19)	0.026 (3)	−0.0028 (16)	0.0058 (17)	−0.0028 (18)
C3	0.020 (2)	0.040 (3)	0.047 (3)	0.000 (2)	0.013 (2)	0.003 (3)
N1	0.0204 (19)	0.0166 (18)	0.017 (2)	0.0018 (14)	0.0050 (14)	−0.0001 (14)
O1	0.0223 (18)	0.0313 (18)	0.036 (2)	0.0042 (15)	0.0086 (14)	0.0102 (16)
O2	0.0268 (18)	0.0239 (17)	0.0253 (19)	0.0024 (14)	0.0065 (14)	0.0065 (14)

C1—N1	1.472 (5)	C3—H3A	0.9800
C1—C2	1.502 (6)	C3—H3B	0.9800
C1—H1D	0.9900	C3—H3C	0.9800
C1—H1E	0.9900	N1—H1A	0.9100
C2—O2	1.194 (5)	N1—H1B	0.9100
C2—O1	1.332 (5)	N1—H1C	0.9100
C3—O1	1.461 (5)
N1—C1—C2	110.5 (4)	H3A—C3—H3B	109.5
N1—C1—H1D	109.6	O1—C3—H3C	109.5
C2—C1—H1D	109.6	H3A—C3—H3C	109.5
N1—C1—H1E	109.6	H3B—C3—H3C	109.5
C2—C1—H1E	109.6	C1—N1—H1A	109.5
H1D—C1—H1E	108.1	C1—N1—H1B	109.5
O2—C2—O1	125.7 (4)	H1A—N1—H1B	109.5
O2—C2—C1	124.2 (4)	C1—N1—H1C	109.5
O1—C2—C1	110.1 (4)	H1A—N1—H1C	109.5
O1—C3—H3A	109.5	H1B—N1—H1C	109.5
O1—C3—H3B	109.5	C2—O1—C3	115.9 (4)
N1—C1—C2—O2	−5.0 (6)	O2—C2—O1—C3	0.9 (7)
N1—C1—C2—O1	175.7 (3)	C1—C2—O1—C3	−179.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.91	2.52	3.269 (4)	140
N1—H1B···Cl1ii	0.91	2.25	3.112 (4)	158
N1—H1C···Cl1	0.91	2.26	3.147 (4)	165
C1—H1D···Cl1iii	0.99	2.69	3.448 (4)	133
C1—H1E···O2i	0.99	2.51	2.928 (4)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.91	2.52	3.269 (4)	140
N1—H1B⋯Cl1ii	0.91	2.25	3.112 (4)	158
N1—H1C⋯Cl1	0.91	2.26	3.147 (4)	165
C1—H1D⋯Cl1iii	0.99	2.69	3.448 (4)	133
C1—H1E⋯O2i	0.99	2.51	2.928 (4)	105

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