2-Carboxy-anilinium bromide monohydrate.

The title compound, C(7)H(8)NO(2) (+)·Br(-)·H(2)O, is isomorphous with 2-carboxy-anilinium chloride monohydrate and contains an intra-molecular N-H⋯O hydrogen bond, forming an S(6) motif. The main inter-molecular inter-actions are of the N-H⋯O/Br and O-H⋯O/Br types. Hydrogen-bonding dimers are formed via the carboxyl groups and the uncoordinated water mol-ecule, with centrosymmetric R(4) (4)(12) ring motifs, in tandem with centrosymmetric R(8) (4)(16) ring motifs formed by the cations and bromide anions. The hydrogen-bonded ring motifs inter-sect, forming chains with graph-set motif C(4) (3)(10) extending along the a axis. These form a two-dimensional hydrogen-bonded network in (101) which is extended along [010] through N-H⋯Br hydrogen bonds. Hydro-philic layers are generated at z = 0 and 1/2 which are sandwiched between alternate hydro-phobic layers across z = 1/4 and 3/4.

Related literature

For background to the applications of l-anthranilic acid, see: Anumula (1993 ▶, 1994 ▶); Ma et al. (2005 ▶); Prager & Skurray (1968 ▶); Robinson (1966 ▶). For related structures, see: Athimoolam & Natarajan (2006 ▶); Bahadur et al. (2007 ▶); Brown & Ehrenberg (1985 ▶); Cinčić & Kaitner 2008 ▶); Zaidi et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a decription of the Cambridge Structural Database, see:Allen (2002 ▶).

Experimental

Crystal data

C7H8NO2 +·Br−·H2O

M = 236.07

Monoclinic,

a = 23.515 (2) Å

b = 4.8923 (4) Å

c = 16.5222 (12) Å

β = 91.569 (5)°

V = 1900.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 4.30 mm−1

T = 293 K

0.25 × 0.14 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

7910 measured reflections

1671 independent reflections

1505 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.07

1671 reflections

133 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.91 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), Mercury (Macrae et al., 2006 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050235/sj2678sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050235/sj2678Isup2.hkl

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

C7H8NO2+·Br−·H2O	F(000) = 944
Mr = 236.07	Dx = 1.650 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3371 reflections
a = 23.515 (2) Å	θ = 2.8–25.0°
b = 4.8923 (4) Å	µ = 4.30 mm−1
c = 16.5222 (12) Å	T = 293 K
β = 91.569 (5)°	Needle, colourless
V = 1900.0 (3) Å3	0.25 × 0.14 × 0.13 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	1505 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 25.0°, θmin = 1.7°
ω scans	h = −27→27
7910 measured reflections	k = −5→5
1671 independent reflections	l = −19→19

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.8797P] where P = (Fo2 + 2Fc2)/3
1671 reflections	(Δ/σ)max = 0.001
133 parameters	Δρmax = 0.91 e Å−3
6 restraints	Δρmin = −0.44 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.30710 (11)	0.7182 (6)	0.10059 (17)	0.0402 (6)
O1	0.32154 (8)	0.5757 (5)	0.04450 (13)	0.0545 (5)
O2	0.25690 (9)	0.6995 (5)	0.13219 (16)	0.0617 (6)
C2	0.34468 (10)	0.9244 (5)	0.14078 (15)	0.0363 (5)
C3	0.32628 (12)	1.0695 (6)	0.20723 (17)	0.0478 (6)
H3	0.2900	1.0379	0.2261	0.057*
C4	0.36070 (15)	1.2595 (7)	0.2458 (2)	0.0546 (8)
H4	0.3474	1.3559	0.2900	0.065*
C5	0.41512 (14)	1.3072 (6)	0.2189 (2)	0.0533 (8)
H5	0.4385	1.4345	0.2451	0.064*
C6	0.43443 (12)	1.1638 (5)	0.15278 (18)	0.0455 (7)
H6	0.4708	1.1954	0.1342	0.055*
C7	0.39988 (10)	0.9755 (5)	0.11468 (14)	0.0346 (5)
N1	0.42208 (10)	0.8318 (5)	0.04455 (15)	0.0392 (5)
H2	0.2382 (16)	0.565 (7)	0.113 (2)	0.087 (13)*
H1A	0.4245 (13)	0.955 (5)	0.0050 (15)	0.051 (9)*
H1B	0.4557 (10)	0.756 (7)	0.055 (2)	0.066 (11)*
H1C	0.3992 (12)	0.695 (5)	0.0301 (19)	0.048 (9)*
O1W	0.19167 (12)	0.3305 (6)	0.0733 (2)	0.0938 (11)
H1W	0.1594 (13)	0.308 (8)	0.090 (3)	0.085 (15)*
H2W	0.198 (3)	0.214 (9)	0.038 (3)	0.13 (2)*
Br1	0.056322 (10)	0.18719 (6)	0.089222 (16)	0.04570 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0318 (14)	0.0467 (15)	0.0424 (16)	−0.0048 (11)	0.0049 (11)	−0.0007 (12)
O1	0.0413 (10)	0.0646 (12)	0.0581 (12)	−0.0159 (10)	0.0136 (9)	−0.0217 (11)
O2	0.0347 (11)	0.0786 (16)	0.0727 (16)	−0.0194 (10)	0.0183 (10)	−0.0272 (12)
C2	0.0318 (12)	0.0408 (13)	0.0366 (13)	−0.0018 (11)	0.0043 (9)	0.0014 (11)
C3	0.0409 (14)	0.0567 (16)	0.0463 (15)	−0.0042 (13)	0.0129 (12)	−0.0058 (14)
C4	0.061 (2)	0.0586 (17)	0.0442 (17)	−0.0067 (15)	0.0098 (15)	−0.0155 (14)
C5	0.0494 (18)	0.0566 (19)	0.0535 (19)	−0.0104 (13)	−0.0046 (14)	−0.0124 (14)
C6	0.0323 (14)	0.0500 (16)	0.0545 (17)	−0.0055 (11)	0.0040 (12)	−0.0045 (12)
C7	0.0301 (12)	0.0377 (13)	0.0360 (13)	0.0007 (10)	0.0039 (9)	0.0015 (10)
N1	0.0297 (12)	0.0440 (13)	0.0443 (13)	−0.0031 (10)	0.0083 (10)	−0.0025 (10)
O1W	0.0483 (15)	0.101 (2)	0.133 (3)	−0.0328 (15)	0.0277 (17)	−0.062 (2)
Br1	0.0333 (2)	0.0562 (2)	0.0477 (2)	−0.00031 (10)	0.00334 (13)	0.00488 (11)

C1—O1	1.216 (3)	C5—C6	1.386 (4)
C1—O2	1.307 (3)	C5—H5	0.9300
C1—C2	1.486 (4)	C6—C7	1.370 (4)
O2—H2	0.85 (3)	C6—H6	0.9300
C2—C3	1.386 (4)	C7—N1	1.464 (3)
C2—C7	1.401 (3)	N1—H1A	0.890 (18)
C3—C4	1.377 (4)	N1—H1B	0.888 (19)
C3—H3	0.9300	N1—H1C	0.886 (18)
C4—C5	1.386 (5)	O1W—H1W	0.82 (3)
C4—H4	0.9300	O1W—H2W	0.83 (3)
O1—C1—O2	122.6 (2)	C4—C5—H5	120.2
O1—C1—C2	123.7 (2)	C7—C6—C5	120.0 (3)
O2—C1—C2	113.7 (2)	C7—C6—H6	120.0
C1—O2—H2	112 (3)	C5—C6—H6	120.0
C3—C2—C7	117.7 (2)	C6—C7—C2	121.4 (2)
C3—C2—C1	120.5 (2)	C6—C7—N1	117.8 (2)
C7—C2—C1	121.9 (2)	C2—C7—N1	120.8 (2)
C4—C3—C2	121.3 (3)	C7—N1—H1A	107 (2)
C4—C3—H3	119.3	C7—N1—H1B	112 (3)
C2—C3—H3	119.3	H1A—N1—H1B	111 (3)
C3—C4—C5	120.1 (3)	C7—N1—H1C	110 (2)
C3—C4—H4	120.0	H1A—N1—H1C	111 (3)
C5—C4—H4	120.0	H1B—N1—H1C	106 (3)
C6—C5—C4	119.5 (3)	H1W—O1W—H2W	109 (5)
C6—C5—H5	120.2
O1—C1—C2—C3	−176.6 (3)	C4—C5—C6—C7	−0.3 (5)
O2—C1—C2—C3	2.2 (4)	C5—C6—C7—C2	0.4 (4)
O1—C1—C2—C7	2.0 (4)	C5—C6—C7—N1	179.3 (3)
O2—C1—C2—C7	−179.3 (3)	C3—C2—C7—C6	−0.6 (4)
C7—C2—C3—C4	0.7 (4)	C1—C2—C7—C6	−179.2 (3)
C1—C2—C3—C4	179.3 (3)	C3—C2—C7—N1	−179.5 (2)
C2—C3—C4—C5	−0.6 (5)	C1—C2—C7—N1	1.9 (4)
C3—C4—C5—C6	0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1W	0.85 (3)	1.70 (3)	2.545 (3)	171 (4)
N1—H1A···Br1i	0.89 (2)	2.39 (1)	3.277 (2)	171 (3)
N1—H1B···Br1ii	0.89 (2)	2.44 (2)	3.299 (2)	163 (3)
N1—H1C···O1	0.89 (2)	1.94 (3)	2.676 (3)	140 (3)
O1W—H2W···O1iii	0.83 (3)	2.01 (4)	2.793 (4)	157 (6)
O1W—H1W···Br1	0.82 (3)	2.49 (3)	3.277 (3)	159 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1W	0.85 (3)	1.70 (3)	2.545 (3)	171 (4)
N1—H1A⋯Br1i	0.89 (2)	2.39 (1)	3.277 (2)	171 (3)
N1—H1B⋯Br1ii	0.89 (2)	2.44 (2)	3.299 (2)	163 (3)
N1—H1C⋯O1	0.89 (2)	1.94 (3)	2.676 (3)	140 (3)
O1W—H2W⋯O1iii	0.83 (3)	2.01 (4)	2.793 (4)	157 (6)
O1W—H1W⋯Br1	0.82 (3)	2.49 (3)	3.277 (3)	159 (4)

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