4-Carb-oxy-anilinium chloride.

In the title salt, C(7)H(8)NO(2) (+)·Cl(-), the cation and anion are linked by an O-H⋯Cl hydrogen bond. The three-dimensional crystal structure is stabilized by N-H⋯O and N-H⋯Cl hydrogen bonds.

Related literature

For related structures, see: Athimoolam & Natarajan (2007 ▶); Gracin & Fischer (2005 ▶).

Experimental

Crystal data

C7H8NO2 +·Cl−

M = 173.59

Monoclinic,

a = 5.601 (5) Å

b = 8.269 (5) Å

c = 17.118 (5) Å

β = 96.371 (5)°

V = 787.9 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 298 K

0.50 × 0.40 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.814, T max = 0.882

4205 measured reflections

1299 independent reflections

1210 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.192

S = 1.26

1299 reflections

133 parameters

All H-atom parameters refined

Δρmax = 0.49 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811046721/wn2458sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046721/wn2458Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046721/wn2458Isup3.cml

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

C7H8NO2+·Cl−	F(000) = 360
Mr = 173.59	Dx = 1.463 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3678 reflections
a = 5.601 (5) Å	θ = 2.4–29.3°
b = 8.269 (5) Å	µ = 0.43 mm−1
c = 17.118 (5) Å	T = 298 K
β = 96.371 (5)°	Block, yellow
V = 787.9 (9) Å3	0.50 × 0.40 × 0.30 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1299 independent reflections
Radiation source: fine-focus sealed tube	1210 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.814, Tmax = 0.882	k = −9→7
4205 measured reflections	l = −20→20

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)] = 0.054	All H-atom parameters refined
wR(F2) = 0.192	w = 1/[σ2(Fo2) + (0.0616P)2 + 2.6608P] where P = (Fo2 + 2Fc2)/3
S = 1.26	(Δ/σ)max < 0.001
1299 reflections	Δρmax = 0.49 e Å−3
133 parameters	Δρmin = −0.34 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: 0.075 (12)

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
C1	0.5758 (9)	0.2824 (5)	0.5157 (3)	0.0322 (11)
C2	0.3637 (8)	0.1926 (6)	0.4999 (3)	0.0332 (11)
C3	0.3059 (9)	0.1230 (6)	0.4273 (3)	0.0367 (12)
C4	0.4607 (8)	0.1434 (5)	0.3701 (3)	0.0314 (11)
C5	0.6671 (9)	0.2347 (6)	0.3835 (3)	0.0362 (12)
C6	0.7245 (9)	0.3053 (6)	0.4564 (3)	0.0376 (12)
C7	0.6379 (9)	0.3487 (6)	0.5964 (3)	0.0348 (11)
N1	0.4043 (9)	0.0640 (6)	0.2933 (3)	0.0374 (10)
O1	0.8194 (7)	0.4512 (5)	0.6027 (2)	0.0488 (11)
O2	0.5313 (8)	0.3078 (5)	0.6508 (2)	0.0573 (12)
Cl1	0.9009 (2)	0.60977 (15)	0.76491 (7)	0.0407 (5)
H1	0.858 (13)	0.482 (9)	0.659 (5)	0.09 (2)*
H1A	0.279 (10)	0.006 (6)	0.293 (3)	0.032 (14)*
H1B	0.393 (14)	0.131 (11)	0.253 (5)	0.09 (3)*
H1C	0.545 (14)	0.002 (9)	0.286 (4)	0.08 (2)*
H2	0.262 (9)	0.183 (6)	0.541 (3)	0.034 (13)*
H3	0.175 (10)	0.067 (6)	0.419 (3)	0.033 (13)*
H5	0.780 (10)	0.249 (6)	0.347 (3)	0.042 (15)*
H6	0.863 (9)	0.363 (6)	0.465 (3)	0.026 (12)*

	U11	U22	U33	U12	U13	U23
C1	0.035 (3)	0.030 (2)	0.033 (2)	0.0025 (19)	0.008 (2)	0.0034 (19)
C2	0.028 (2)	0.039 (3)	0.034 (2)	0.001 (2)	0.008 (2)	0.006 (2)
C3	0.033 (3)	0.035 (3)	0.045 (3)	−0.004 (2)	0.013 (2)	0.003 (2)
C4	0.033 (2)	0.028 (2)	0.035 (2)	0.0035 (19)	0.009 (2)	0.0035 (18)
C5	0.035 (3)	0.040 (3)	0.036 (3)	0.000 (2)	0.013 (2)	0.005 (2)
C6	0.033 (3)	0.037 (3)	0.046 (3)	−0.007 (2)	0.015 (2)	−0.001 (2)
C7	0.031 (2)	0.038 (2)	0.034 (2)	0.002 (2)	0.002 (2)	0.003 (2)
N1	0.036 (2)	0.041 (2)	0.035 (2)	−0.004 (2)	0.006 (2)	0.0016 (19)
O1	0.054 (2)	0.054 (2)	0.039 (2)	−0.0211 (19)	0.0078 (19)	−0.0046 (17)
O2	0.059 (3)	0.080 (3)	0.035 (2)	−0.025 (2)	0.014 (2)	−0.0088 (19)
Cl1	0.0353 (8)	0.0408 (8)	0.0459 (8)	0.0035 (5)	0.0043 (5)	−0.0016 (5)

C1—C6	1.395 (6)	C5—C6	1.383 (7)
C1—C2	1.402 (7)	C5—H5	0.94 (5)
C1—C7	1.491 (7)	C6—H6	0.91 (5)
C2—C3	1.374 (7)	C7—O2	1.209 (6)
C2—H2	0.96 (5)	C7—O1	1.319 (6)
C3—C4	1.389 (6)	N1—H1A	0.85 (6)
C3—H3	0.87 (6)	N1—H1B	0.88 (9)
C4—C5	1.378 (7)	N1—H1C	0.96 (8)
C4—N1	1.471 (7)	O1—H1	0.99 (8)
C6—C1—C2	119.6 (5)	C6—C5—H5	116 (3)
C6—C1—C7	121.8 (5)	C5—C6—C1	120.1 (5)
C2—C1—C7	118.6 (4)	C5—C6—H6	118 (3)
C3—C2—C1	120.4 (4)	C1—C6—H6	121 (3)
C3—C2—H2	122 (3)	O2—C7—O1	124.0 (5)
C1—C2—H2	117 (3)	O2—C7—C1	121.8 (5)
C2—C3—C4	119.0 (5)	O1—C7—C1	114.2 (4)
C2—C3—H3	118 (3)	C4—N1—H1A	111 (3)
C4—C3—H3	123 (3)	C4—N1—H1B	114 (5)
C5—C4—C3	121.7 (5)	H1A—N1—H1B	111 (6)
C5—C4—N1	119.1 (4)	C4—N1—H1C	104 (5)
C3—C4—N1	119.1 (4)	H1A—N1—H1C	113 (6)
C4—C5—C6	119.3 (4)	H1B—N1—H1C	103 (6)
C4—C5—H5	125 (3)	C7—O1—H1	109 (4)
C6—C1—C2—C3	2.1 (7)	C4—C5—C6—C1	0.7 (8)
C7—C1—C2—C3	−176.9 (4)	C2—C1—C6—C5	−2.3 (7)
C1—C2—C3—C4	−0.1 (7)	C7—C1—C6—C5	176.6 (5)
C2—C3—C4—C5	−1.6 (7)	C6—C1—C7—O2	−167.9 (5)
C2—C3—C4—N1	177.7 (4)	C2—C1—C7—O2	11.1 (7)
C3—C4—C5—C6	1.4 (7)	C6—C1—C7—O1	10.8 (7)
N1—C4—C5—C6	−177.9 (5)	C2—C1—C7—O1	−170.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl1	0.99 (8)	2.10 (8)	3.059 (4)	164 (6)
N1—H1A···Cl1i	0.85 (6)	2.33 (6)	3.154 (6)	165 (5)
N1—H1B···O2ii	0.88 (9)	2.05 (8)	2.823 (6)	145 (7)
N1—H1B···Cl1iii	0.88 (9)	2.70 (9)	3.289 (5)	125 (6)
N1—H1C···Cl1ii	0.96 (8)	2.26 (8)	3.215 (5)	172 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl1	0.99 (8)	2.10 (8)	3.059 (4)	164 (6)
N1—H1A⋯Cl1i	0.85 (6)	2.33 (6)	3.154 (6)	165 (5)
N1—H1B⋯O2ii	0.88 (9)	2.05 (8)	2.823 (6)	145 (7)
N1—H1B⋯Cl1iii	0.88 (9)	2.70 (9)	3.289 (5)	125 (6)
N1—H1C⋯Cl1ii	0.96 (8)	2.26 (8)	3.215 (5)	172 (6)

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