4-(Carboxy-meth-yl)anilinium chloride.

In the crystal of the title compound, C(8)H(10)NO(2) (+)·Cl(-), alternating layers of hydro-phobic and hydro-philic zones stack along the c axis. The chloride anions are sandwiched between the 4-(carboxy-meth-yl)anilinium layers, forming inter-molecular O-H⋯Cl and N-H⋯Cl hydrogen bonds with the ammonium and carboxyl groups of the cations. In addition, inter-molecular N-H⋯O and weak C-H⋯O and C-H⋯Cl hydrogen bonds help stabilize the crystal structure.

Related literature

For our ongoing studies of hydrogen-bonding inter­actions in the crystal structures of protonated amines, see: Benslimane et al. (2007 ▶); Bouacida et al. (2005a ▶,b ▶,c ▶, 2006 ▶, 2007 ▶, 2008 ▶, 2009 ▶). For amino acids in which the amino N atom is protonated, see: Bouacida et al. (2006); Rademeyer (2004a ▶,b ▶). For a related structure, see: Benslimane et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H10NO2 +·Cl−

M = 187.62

Monoclinic,

a = 4.4982 (4) Å

b = 11.0790 (11) Å

c = 17.7120 (17) Å

β = 95.429 (3)°

V = 878.73 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 100 K

0.44 × 0.12 × 0.1 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.809, T max = 0.962

7536 measured reflections

2006 independent reflections

1785 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.08

S = 1.03

2006 reflections

113 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021849/lh2838sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021849/lh2838Isup2.hkl

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

C8H10NO2+·Cl−	F(000) = 392
Mr = 187.62	Dx = 1.418 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3208 reflections
a = 4.4982 (4) Å	θ = 2.3–27.4°
b = 11.0790 (11) Å	µ = 0.39 mm−1
c = 17.7120 (17) Å	T = 100 K
β = 95.429 (3)°	Stick, white
V = 878.73 (14) Å3	0.44 × 0.12 × 0.1 mm
Z = 4

Bruker APEXII diffractometer	1785 reflections with I > 2σ(I)
graphite	Rint = 0.040
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→5
Tmin = 0.809, Tmax = 0.962	k = −14→14
7536 measured reflections	l = −22→22
2006 independent reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.08	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0283P)2 + 0.5301P] where P = (Fo2 + 2Fc2)/3
2006 reflections	(Δ/σ)max = 0.001
113 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.22 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	0.33999 (7)	0.14718 (3)	0.035821 (18)	0.01567 (11)
O1	0.7756 (3)	0.59938 (11)	0.02054 (6)	0.0270 (3)
H1	0.7238	0.6660	0.0040	0.040*
O2	0.5016 (3)	0.65210 (10)	0.11399 (6)	0.0257 (3)
N1	0.3016 (3)	0.37706 (11)	0.40929 (7)	0.0145 (3)
H1A	0.1824	0.3128	0.4051	0.022*
H1B	0.1969	0.4414	0.4212	0.022*
H1C	0.4494	0.3642	0.4455	0.022*
C1	0.4271 (3)	0.39836 (13)	0.33671 (8)	0.0126 (3)
C2	0.3601 (3)	0.32006 (13)	0.27659 (8)	0.0148 (3)
H2	0.2377	0.2535	0.2817	0.018*
C3	0.4804 (3)	0.34312 (13)	0.20801 (8)	0.0155 (3)
H3	0.4373	0.2911	0.1672	0.019*
C4	0.6631 (3)	0.44257 (13)	0.19984 (8)	0.0145 (3)
C5	0.7279 (3)	0.51913 (14)	0.26215 (8)	0.0176 (3)
H5	0.8524	0.5853	0.2576	0.021*
C6	0.6098 (3)	0.49813 (14)	0.33049 (8)	0.0166 (3)
H6	0.6522	0.5499	0.3714	0.020*
C7	0.7903 (3)	0.46817 (14)	0.12557 (8)	0.0180 (3)
H7A	0.7456	0.4006	0.0916	0.022*
H7B	1.0060	0.4744	0.1347	0.022*
C8	0.6709 (3)	0.58249 (14)	0.08711 (8)	0.0157 (3)

	U11	U22	U33	U12	U13	U23
Cl1	0.01972 (19)	0.01379 (19)	0.01353 (18)	0.00041 (13)	0.00178 (13)	0.00186 (12)
O1	0.0392 (7)	0.0206 (6)	0.0239 (6)	0.0128 (5)	0.0181 (5)	0.0103 (5)
O2	0.0361 (7)	0.0226 (6)	0.0203 (6)	0.0151 (5)	0.0123 (5)	0.0061 (5)
N1	0.0169 (6)	0.0146 (6)	0.0124 (6)	−0.0011 (5)	0.0034 (5)	−0.0013 (5)
C4	0.0141 (6)	0.0146 (7)	0.0150 (7)	0.0054 (5)	0.0026 (5)	0.0034 (5)
C1	0.0131 (6)	0.0142 (7)	0.0108 (6)	0.0020 (5)	0.0025 (5)	0.0023 (5)
C6	0.0173 (7)	0.0163 (7)	0.0160 (7)	−0.0025 (6)	0.0003 (5)	−0.0027 (6)
C3	0.0190 (7)	0.0138 (7)	0.0137 (7)	0.0024 (6)	0.0011 (5)	−0.0020 (5)
C7	0.0199 (7)	0.0173 (7)	0.0178 (7)	0.0043 (6)	0.0071 (6)	0.0034 (6)
C8	0.0156 (7)	0.0161 (7)	0.0157 (7)	0.0003 (6)	0.0034 (5)	0.0007 (6)
C5	0.0152 (7)	0.0173 (7)	0.0206 (7)	−0.0039 (6)	0.0032 (5)	0.0013 (6)
C2	0.0161 (6)	0.0123 (7)	0.0159 (7)	−0.0021 (6)	0.0014 (5)	0.0000 (6)

O1—C8	1.3234 (17)	C1—C6	1.388 (2)
O1—H1	0.8200	C6—C5	1.387 (2)
O2—C8	1.2121 (18)	C6—H6	0.9300
N1—C1	1.4709 (17)	C3—C2	1.399 (2)
N1—H1A	0.8900	C3—H3	0.9300
N1—H1B	0.8900	C7—C8	1.512 (2)
N1—H1C	0.8900	C7—H7A	0.9700
C4—C3	1.390 (2)	C7—H7B	0.9700
C4—C5	1.401 (2)	C5—H5	0.9300
C4—C7	1.5100 (19)	C2—H2	0.9300
C1—C2	1.384 (2)
C8—O1—H1	109.5	C4—C3—H3	119.5
C1—N1—H1A	109.5	C2—C3—H3	119.5
C1—N1—H1B	109.5	C4—C7—C8	113.72 (12)
H1A—N1—H1B	109.5	C4—C7—H7A	108.8
C1—N1—H1C	109.5	C8—C7—H7A	108.8
H1A—N1—H1C	109.5	C4—C7—H7B	108.8
H1B—N1—H1C	109.5	C8—C7—H7B	108.8
C3—C4—C5	118.62 (13)	H7A—C7—H7B	107.7
C3—C4—C7	121.06 (13)	O2—C8—O1	123.32 (14)
C5—C4—C7	120.33 (13)	O2—C8—C7	124.41 (13)
C2—C1—C6	121.69 (13)	O1—C8—C7	112.27 (12)
C2—C1—N1	119.89 (12)	C6—C5—C4	121.20 (14)
C6—C1—N1	118.42 (12)	C6—C5—H5	119.4
C5—C6—C1	118.77 (13)	C4—C5—H5	119.4
C5—C6—H6	120.6	C1—C2—C3	118.67 (13)
C1—C6—H6	120.6	C1—C2—H2	120.7
C4—C3—C2	121.05 (13)	C3—C2—H2	120.7
C2—C1—C6—C5	−0.1 (2)	C4—C7—C8—O1	−176.97 (13)
N1—C1—C6—C5	−179.72 (13)	C1—C6—C5—C4	0.7 (2)
C5—C4—C3—C2	0.7 (2)	C3—C4—C5—C6	−1.0 (2)
C7—C4—C3—C2	−179.38 (13)	C7—C4—C5—C6	179.07 (13)
C3—C4—C7—C8	113.71 (16)	C6—C1—C2—C3	−0.2 (2)
C5—C4—C7—C8	−66.37 (18)	N1—C1—C2—C3	179.42 (12)
C4—C7—C8—O2	3.9 (2)	C4—C3—C2—C1	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1i	0.82	2.20	3.0087 (13)	171
N1—H1A···O2ii	0.89	1.98	2.8517 (17)	167
N1—H1B···Cl1iii	0.89	2.41	3.2285 (13)	152
N1—H1C···Cl1iv	0.89	2.26	3.1516 (14)	174
C2—H2···O2ii	0.93	2.49	3.2338 (18)	137
C3—H3···Cl1	0.93	2.82	3.7481 (15)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1i	0.82	2.20	3.0087 (13)	171
N1—H1A⋯O2ii	0.89	1.98	2.8517 (17)	167
N1—H1B⋯Cl1iii	0.89	2.41	3.2285 (13)	152
N1—H1C⋯Cl1iv	0.89	2.26	3.1516 (14)	174
C2—H2⋯O2ii	0.93	2.49	3.2338 (18)	137
C3—H3⋯Cl1	0.93	2.82	3.7481 (15)	175

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