2-Amino-4-chloro-benzoic acid.

The title compound, C(7)H(6)ClNO(2), is almost planar, with an r.m.s. deviation of 0.040 Å. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of O-H⋯O hydrogen bonds. These dimers are stacked along [010].

Related literature

For the pharmacological properties of quinazolinone derivatives, see: Prakash Naik et al. (2009 ▶); Bembenek et al. (2010 ▶); Miller et al. (2010 ▶); Sikorska et al. (1998 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H6ClNO2

M = 171.58

Monoclinic,

a = 15.4667 (10) Å

b = 3.7648 (2) Å

c = 23.7598 (15) Å

β = 93.015 (3)°

V = 1381.59 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.49 mm−1

T = 100 K

0.53 × 0.17 × 0.05 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.780, T max = 0.975

34764 measured reflections

3645 independent reflections

3175 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.089

S = 1.07

3645 reflections

112 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050166/hb5757sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050166/hb5757Isup2.hkl

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

C7H6ClNO2	F(000) = 704
Mr = 171.58	Dx = 1.650 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9945 reflections
a = 15.4667 (10) Å	θ = 2.6–37.5°
b = 3.7648 (2) Å	µ = 0.49 mm−1
c = 23.7598 (15) Å	T = 100 K
β = 93.015 (3)°	Needle, orange
V = 1381.59 (14) Å3	0.53 × 0.17 × 0.05 mm
Z = 8

Bruker APEXII DUO CCD diffractometer	3645 independent reflections
Radiation source: fine-focus sealed tube	3175 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 37.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.780, Tmax = 0.975	k = −6→6
34764 measured reflections	l = −38→40

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.5195P] where P = (Fo2 + 2Fc2)/3
3645 reflections	(Δ/σ)max = 0.001
112 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.400495 (11)	0.03406 (5)	0.207389 (8)	0.02000 (6)
O1	0.01970 (4)	0.31432 (19)	0.06195 (2)	0.02250 (12)
O2	0.11545 (4)	0.57721 (19)	0.00817 (2)	0.02167 (12)
N1	0.07764 (4)	0.0546 (2)	0.16254 (3)	0.02152 (13)
C1	0.15675 (4)	0.1453 (2)	0.14497 (3)	0.01451 (11)
C2	0.23039 (4)	0.0671 (2)	0.18024 (3)	0.01549 (12)
H2A	0.2241	−0.0407	0.2150	0.019*
C3	0.31151 (4)	0.1502 (2)	0.16319 (3)	0.01506 (11)
C4	0.32545 (4)	0.3164 (2)	0.11206 (3)	0.01691 (12)
H4A	0.3810	0.3700	0.1015	0.020*
C5	0.25346 (4)	0.3983 (2)	0.07761 (3)	0.01614 (12)
H5A	0.2610	0.5113	0.0434	0.019*
C6	0.16899 (4)	0.31592 (19)	0.09275 (3)	0.01417 (11)
C7	0.09544 (5)	0.4008 (2)	0.05369 (3)	0.01611 (12)
H1O2	0.0692 (10)	0.603 (5)	−0.0126 (7)	0.038 (4)*
H1N1	0.0309 (10)	0.083 (4)	0.1425 (6)	0.034 (4)*
H2N1	0.0757 (11)	−0.069 (5)	0.1911 (7)	0.042 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01555 (8)	0.02243 (10)	0.02140 (9)	0.00327 (6)	−0.00502 (6)	−0.00029 (6)
O1	0.0145 (2)	0.0335 (3)	0.0191 (2)	−0.0014 (2)	−0.00278 (17)	0.0055 (2)
O2	0.0174 (2)	0.0316 (3)	0.0157 (2)	−0.0006 (2)	−0.00240 (18)	0.0067 (2)
N1	0.0141 (2)	0.0308 (4)	0.0196 (3)	−0.0016 (2)	0.0007 (2)	0.0075 (3)
C1	0.0134 (2)	0.0150 (3)	0.0150 (2)	0.0001 (2)	−0.00005 (19)	0.0001 (2)
C2	0.0147 (3)	0.0169 (3)	0.0146 (2)	0.0013 (2)	−0.0012 (2)	0.0011 (2)
C3	0.0136 (2)	0.0155 (3)	0.0158 (2)	0.0016 (2)	−0.00237 (19)	−0.0019 (2)
C4	0.0134 (2)	0.0203 (3)	0.0169 (3)	−0.0005 (2)	−0.0001 (2)	−0.0009 (2)
C5	0.0152 (3)	0.0187 (3)	0.0144 (2)	−0.0007 (2)	0.0000 (2)	−0.0002 (2)
C6	0.0139 (2)	0.0154 (3)	0.0130 (2)	0.0005 (2)	−0.00089 (19)	−0.0004 (2)
C7	0.0159 (3)	0.0183 (3)	0.0140 (2)	0.0013 (2)	−0.00138 (19)	−0.0003 (2)

Cl1—C3	1.7425 (7)	C2—C3	1.3746 (10)
O1—C7	1.2415 (9)	C2—H2A	0.9300
O2—C7	1.3197 (9)	C3—C4	1.3933 (10)
O2—H1O2	0.854 (16)	C4—C5	1.3816 (10)
N1—C1	1.3572 (9)	C4—H4A	0.9300
N1—H1N1	0.851 (16)	C5—C6	1.4078 (9)
N1—H2N1	0.826 (17)	C5—H5A	0.9300
C1—C2	1.4093 (10)	C6—C7	1.4651 (10)
C1—C6	1.4185 (9)
C7—O2—H1O2	107.8 (11)	C5—C4—C3	117.38 (6)
C1—N1—H1N1	123.2 (10)	C5—C4—H4A	121.3
C1—N1—H2N1	117.9 (12)	C3—C4—H4A	121.3
H1N1—N1—H2N1	117.7 (15)	C4—C5—C6	121.95 (7)
N1—C1—C2	118.55 (6)	C4—C5—H5A	119.0
N1—C1—C6	123.17 (6)	C6—C5—H5A	119.0
C2—C1—C6	118.28 (6)	C5—C6—C1	119.45 (6)
C3—C2—C1	119.92 (6)	C5—C6—C7	119.34 (6)
C3—C2—H2A	120.0	C1—C6—C7	121.20 (6)
C1—C2—H2A	120.0	O1—C7—O2	121.70 (7)
C2—C3—C4	123.01 (6)	O1—C7—C6	123.38 (7)
C2—C3—Cl1	118.00 (5)	O2—C7—C6	114.92 (6)
C4—C3—Cl1	118.99 (5)
N1—C1—C2—C3	178.90 (7)	N1—C1—C6—C5	−179.53 (8)
C6—C1—C2—C3	−1.19 (11)	C2—C1—C6—C5	0.57 (11)
C1—C2—C3—C4	0.96 (12)	N1—C1—C6—C7	−0.92 (12)
C1—C2—C3—Cl1	−177.87 (6)	C2—C1—C6—C7	179.18 (7)
C2—C3—C4—C5	−0.05 (12)	C5—C6—C7—O1	174.64 (7)
Cl1—C3—C4—C5	178.77 (6)	C1—C6—C7—O1	−3.97 (12)
C3—C4—C5—C6	−0.59 (12)	C5—C6—C7—O2	−5.06 (11)
C4—C5—C6—C1	0.33 (11)	C1—C6—C7—O2	176.34 (7)
C4—C5—C6—C7	−178.31 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1i	0.853 (16)	1.787 (16)	2.6354 (8)	173.0 (16)
N1—H1N1···O1	0.851 (15)	2.102 (14)	2.6918 (9)	126.0 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1i	0.853 (16)	1.787 (16)	2.6354 (8)	173.0 (16)
N1—H1N1⋯O1	0.851 (15)	2.102 (14)	2.6918 (9)	126.0 (13)

Symmetry code: (i) .