2-Carboxy-anilinium chloride monohydrate.

In the mol-ecule of the title compound, C(7)H(8)NO(2) (+)·Cl(-)·H(2)O, an intra-molecular N-H⋯O hydrogen bond results in the formation of a non-planar six-membered ring adopting a flattened boat conformation. In the crystal structure, inter-molecular O-H⋯O and N-H⋯Cl hydrogen bonds link the mol-ecules. There is a C=O⋯π contact between the carbonyl unit and the centroid of the benzene ring. There is a C=O⋯π contact [C⋯Cg = 3.5802 (18), C-O⋯Cg = 89 (1)°] between the carbonyl unit and the centroid of the benzene ring.

Related literature

For applications of anthranilic acid derivatives, see: Congiu et al. (2005 ▶); Nittoli et al. (2005 ▶). For a related structure, see: Bahadur et al. (2007 ▶); For bond-length data, see: Allen et al. (1987 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C7H8NO2 +·Cl−·H2O

M = 191.61

Monoclinic,

a = 23.094 (4) Å

b = 4.7833 (8) Å

c = 16.381 (3) Å

β = 91.605 (9)°

V = 1808.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.39 mm−1

T = 296 (2) K

0.28 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.985

9747 measured reflections

2238 independent reflections

1749 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.05

2238 reflections

139 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks text, I. DOI: 10.1107/S1600536808029267/hk2527sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029267/hk2527Isup2.hkl

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

C7H8NO2+·Cl−·H2O	F(000) = 800
Mr = 191.61	Dx = 1.407 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2238 reflections
a = 23.094 (4) Å	θ = 2.5–28.3°
b = 4.7833 (8) Å	µ = 0.39 mm−1
c = 16.381 (3) Å	T = 296 K
β = 91.605 (9)°	Prism, brown
V = 1808.8 (5) Å3	0.28 × 0.10 × 0.06 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2238 independent reflections
Radiation source: fine-focus sealed tube	1749 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.5 pixels mm-1	θmax = 28.3°, θmin = 2.5°
ω scans	h = −30→30
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→3
Tmin = 0.975, Tmax = 0.985	l = −21→20
9747 measured 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0476P)2 + 1.0872P] where P = (Fo2 + 2Fc2)/3
2238 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.05634 (2)	0.81018 (10)	0.08328 (3)	0.0425 (2)
O1	0.24332 (5)	0.7928 (3)	0.36801 (9)	0.0551 (5)
O2	0.17708 (5)	0.9236 (3)	0.45555 (8)	0.0493 (4)
O3	0.18909 (7)	0.6690 (4)	0.07558 (14)	0.0796 (7)
N1	0.07438 (6)	0.6617 (3)	0.45470 (9)	0.0340 (4)
C1	0.19199 (7)	0.7781 (3)	0.39900 (10)	0.0338 (5)
C2	0.15328 (6)	0.5699 (3)	0.35784 (9)	0.0304 (4)
C3	0.17259 (8)	0.4219 (4)	0.29012 (10)	0.0408 (5)
C4	0.13710 (9)	0.2318 (4)	0.25017 (11)	0.0462 (6)
C5	0.08157 (8)	0.1841 (4)	0.27706 (12)	0.0466 (6)
C6	0.06160 (7)	0.3269 (4)	0.34388 (11)	0.0398 (5)
C7	0.09727 (6)	0.5188 (3)	0.38354 (9)	0.0300 (4)
H1	0.2619 (10)	0.922 (5)	0.3885 (14)	0.0661*
H1A	0.0991 (9)	0.802 (4)	0.4684 (12)	0.0510*
H1B	0.0399 (10)	0.732 (4)	0.4423 (13)	0.0510*
H1C	0.0724 (9)	0.534 (4)	0.4996 (12)	0.0510*
H3	0.2113 (9)	0.452 (4)	0.2717 (11)	0.0489*
H3A	0.1584 (14)	0.692 (7)	0.0892 (19)	0.0955*
H3B	0.1945 (14)	0.777 (6)	0.041 (2)	0.0955*
H4	0.1511 (9)	0.133 (5)	0.2061 (13)	0.0554*
H5	0.0582 (9)	0.052 (4)	0.2493 (12)	0.0558*
H6	0.0245 (9)	0.298 (4)	0.3628 (12)	0.0477*

	U11	U22	U33	U12	U13	U23
Cl1	0.0314 (2)	0.0499 (3)	0.0463 (3)	−0.0004 (2)	0.0035 (2)	−0.0055 (2)
O1	0.0320 (7)	0.0668 (9)	0.0673 (9)	−0.0189 (6)	0.0174 (6)	−0.0255 (7)
O2	0.0401 (7)	0.0554 (8)	0.0531 (7)	−0.0144 (6)	0.0133 (6)	−0.0206 (6)
O3	0.0408 (8)	0.0837 (13)	0.1153 (15)	0.0249 (8)	0.0207 (9)	0.0514 (11)
N1	0.0255 (7)	0.0362 (8)	0.0406 (8)	−0.0012 (6)	0.0081 (5)	−0.0030 (6)
C1	0.0283 (8)	0.0362 (8)	0.0372 (8)	−0.0030 (6)	0.0049 (6)	0.0006 (7)
C2	0.0279 (7)	0.0312 (8)	0.0323 (7)	−0.0017 (6)	0.0041 (6)	0.0009 (6)
C3	0.0357 (9)	0.0456 (10)	0.0416 (9)	−0.0040 (8)	0.0111 (7)	−0.0063 (8)
C4	0.0512 (11)	0.0487 (10)	0.0391 (9)	−0.0031 (8)	0.0077 (8)	−0.0135 (8)
C5	0.0445 (10)	0.0462 (10)	0.0486 (10)	−0.0088 (8)	−0.0048 (8)	−0.0109 (8)
C6	0.0292 (8)	0.0435 (10)	0.0466 (9)	−0.0053 (7)	0.0018 (7)	−0.0030 (8)
C7	0.0278 (7)	0.0307 (8)	0.0315 (7)	0.0005 (6)	0.0031 (6)	0.0014 (6)

O1—C1	1.304 (2)	C2—C3	1.399 (2)
O2—C1	1.216 (2)	C2—C7	1.393 (2)
O1—H1	0.82 (2)	C3—C4	1.377 (3)
O3—H3B	0.78 (3)	C4—C5	1.387 (3)
O3—H3A	0.76 (3)	C5—C6	1.380 (3)
N1—C7	1.463 (2)	C6—C7	1.383 (2)
N1—H1B	0.88 (2)	C3—H3	0.96 (2)
N1—H1C	0.958 (19)	C4—H4	0.93 (2)
N1—H1A	0.91 (2)	C5—H5	0.94 (2)
C1—C2	1.487 (2)	C6—H6	0.93 (2)
Cl1···O3	3.1452 (18)	N1···O2	2.6820 (19)
Cl1···N1i	3.3227 (16)	C1···C3iv	3.581 (2)
Cl1···N1ii	3.1464 (16)	C1···O3vi	3.339 (2)
Cl1···N1iii	3.1231 (16)	C1···C4iv	3.477 (3)
Cl1···H5iv	2.96 (2)	C3···C1x	3.581 (2)
Cl1···H3A	2.42 (3)	C3···O1viii	3.338 (2)
Cl1···H6v	3.13 (2)	C4···C1x	3.477 (3)
Cl1···H1Bii	2.28 (2)	C1···H1A	2.46 (2)
Cl1···H1Ai	2.84 (2)	H1···H3Bvi	2.27 (4)
Cl1···H1Ciii	2.181 (19)	H1···H3Avi	2.27 (4)
O1···C3vi	3.338 (2)	H1···O3vi	1.73 (2)
O1···O3vi	2.539 (2)	H1A···C1	2.46 (2)
O2···O3vii	2.777 (3)	H1A···O2	1.91 (2)
O2···N1	2.6820 (19)	H1A···Cl1vii	2.84 (2)
O3···O2i	2.777 (3)	H1B···Cl1ii	2.28 (2)
O3···O1viii	2.539 (2)	H1B···H6	2.47 (3)
O3···C1viii	3.339 (2)	H1C···Cl1ix	2.181 (19)
O3···Cl1	3.1452 (18)	H3···O1	2.372 (19)
O1···H4vi	2.86 (2)	H3···O1viii	2.655 (19)
O1···H3vi	2.655 (19)	H3A···O2i	2.90 (3)
O1···H3	2.372 (19)	H3A···H1viii	2.27 (4)
O2···H3Avii	2.90 (3)	H3A···Cl1	2.42 (3)
O2···H3Bvii	2.04 (3)	H3B···H1viii	2.27 (4)
O2···H1A	1.91 (2)	H3B···O2i	2.04 (3)
O3···H1viii	1.73 (2)	H4···O1viii	2.86 (2)
N1···Cl1ix	3.1231 (16)	H5···Cl1x	2.96 (2)
N1···Cl1vii	3.3227 (16)	H6···Cl1xi	3.13 (2)
N1···Cl1ii	3.1464 (16)	H6···H1B	2.47 (3)
C1—O1—H1	110.7 (16)	C3—C4—C5	120.07 (17)
H3A—O3—H3B	107 (3)	C4—C5—C6	120.20 (17)
C7—N1—H1C	109.9 (12)	C5—C6—C7	119.54 (15)
H1A—N1—H1B	109.5 (18)	N1—C7—C2	121.21 (13)
H1B—N1—H1C	110.9 (19)	C2—C7—C6	121.35 (14)
C7—N1—H1A	107.7 (13)	N1—C7—C6	117.43 (13)
H1A—N1—H1C	109.0 (17)	C2—C3—H3	119.5 (11)
C7—N1—H1B	109.8 (14)	C4—C3—H3	119.7 (11)
O1—C1—O2	123.05 (15)	C5—C4—H4	120.6 (13)
O1—C1—C2	113.64 (14)	C3—C4—H4	119.3 (13)
O2—C1—C2	123.31 (15)	C4—C5—H5	118.7 (13)
C3—C2—C7	118.04 (14)	C6—C5—H5	121.1 (13)
C1—C2—C7	122.14 (13)	C5—C6—H6	121.5 (12)
C1—C2—C3	119.82 (14)	C7—C6—H6	119.0 (12)
C2—C3—C4	120.80 (17)
O1—C1—C2—C3	−2.8 (2)	C3—C2—C7—N1	178.91 (14)
O1—C1—C2—C7	178.32 (14)	C3—C2—C7—C6	0.3 (2)
O2—C1—C2—C3	176.32 (16)	C2—C3—C4—C5	−0.3 (3)
O2—C1—C2—C7	−2.5 (2)	C3—C4—C5—C6	0.1 (3)
C1—C2—C3—C4	−178.82 (16)	C4—C5—C6—C7	0.3 (3)
C7—C2—C3—C4	0.1 (2)	C5—C6—C7—N1	−179.16 (16)
C1—C2—C7—N1	−2.2 (2)	C5—C6—C7—C2	−0.5 (3)
C1—C2—C7—C6	179.17 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3vi	0.82 (2)	1.73 (2)	2.539 (2)	171 (2)
N1—H1A···O2	0.91 (2)	1.91 (2)	2.6820 (19)	142.1 (18)
N1—H1B···Cl1ii	0.88 (2)	2.28 (2)	3.1464 (16)	166.6 (18)
N1—H1C···Cl1ix	0.958 (19)	2.181 (19)	3.1231 (16)	167.5 (18)
O3—H3A···Cl1	0.76 (3)	2.42 (3)	3.1452 (18)	160 (3)
O3—H3B···O2i	0.78 (3)	2.04 (3)	2.777 (3)	159 (3)
C1—O2···Cgiv	1.216 (2)	3.3988 (16)	3.5802 (18)	88.5 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82 (2)	1.73 (2)	2.539 (2)	171 (2)
N1—H1A⋯O2	0.91 (2)	1.91 (2)	2.6820 (19)	142.1 (18)
N1—H1B⋯Cl1ii	0.88 (2)	2.28 (2)	3.1464 (16)	166.6 (18)
N1—H1C⋯Cl1iii	0.958 (19)	2.181 (19)	3.1231 (16)	167.5 (18)
O3—H3A⋯Cl1	0.76 (3)	2.42 (3)	3.1452 (18)	160 (3)
O3—H3B⋯O2iv	0.78 (3)	2.04 (3)	2.777 (3)	159 (3)

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