3-[(3,4-Dichloro-phen-yl)amino-carbon-yl]propionic acid.

In the title compound, C(10)H(9)Cl(2)NO(3), inversion dimers occur due to pairs of inter-molecular O-H⋯O hydrogen bonds from the carboxyl groups forming R(2) (2)(8) loops. The dimers are linked into C(4) chains along the a axis by inter-molecular N-H⋯O links. A short intra-molecular C-H⋯O contact occurs in the mol-ecule.

Related literature

For a related structure, see: Shah et al. (2008 ▶). For background, see: Pellerito & Nagy (2002 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9Cl2NO3

M = 262.08

Monoclinic,

a = 4.8441 (4) Å

b = 10.3388 (10) Å

c = 22.457 (2) Å

β = 90.613 (3)°

V = 1124.62 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.57 mm−1

T = 296 K

0.25 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.925, T max = 0.949

11915 measured reflections

2912 independent reflections

2028 reflections with I > 3σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.182

S = 1.05

2912 reflections

172 parameters

Only H-atom coordinates refined

Δρmax = 0.89 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015025/hb2958sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015025/hb2958Isup2.hkl

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

C10H9Cl2NO3	F(000) = 536
Mr = 262.08	Dx = 1.548 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2912 reflections
a = 4.8441 (4) Å	θ = 2.7–28.9°
b = 10.3388 (10) Å	µ = 0.57 mm−1
c = 22.457 (2) Å	T = 296 K
β = 90.613 (3)°	Block, colourless
V = 1124.62 (17) Å3	0.25 × 0.12 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2912 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 3σ(I)
graphite	Rint = 0.028
Detector resolution: 7.5 pixels mm-1	θmax = 28.9°, θmin = 2.7°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.925, Tmax = 0.949	l = −30→30
11915 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	Only H-atom coordinates refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0667P)2 + 1.6338P] where P = (Fo2 + 2Fc2)/3
2912 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.84 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	0.2707 (3)	0.56808 (11)	0.26822 (5)	0.0954 (5)
Cl2	0.6942 (3)	0.37607 (10)	0.20648 (6)	0.0945 (5)
O1	0.7844 (5)	1.3991 (2)	−0.01026 (13)	0.0584 (9)
O2	0.4038 (4)	1.3685 (2)	0.04204 (12)	0.0551 (8)
O3	0.9245 (4)	0.9675 (2)	0.08819 (12)	0.0546 (8)
N1	0.4948 (5)	0.9009 (2)	0.11088 (11)	0.0372 (7)
C1	0.5572 (5)	0.7772 (3)	0.13420 (12)	0.0341 (8)
C2	0.4079 (7)	0.7353 (3)	0.18269 (14)	0.0427 (9)
C3	0.4538 (8)	0.6133 (3)	0.20585 (14)	0.0500 (10)
C4	0.6432 (8)	0.5320 (3)	0.18016 (16)	0.0543 (11)
C5	0.7934 (8)	0.5742 (3)	0.13222 (18)	0.0568 (11)
C6	0.7517 (7)	0.6968 (3)	0.10907 (15)	0.0448 (9)
C7	0.6785 (5)	0.9883 (3)	0.09118 (12)	0.0345 (8)
C8	0.5505 (6)	1.1164 (3)	0.07282 (17)	0.0438 (9)
C9	0.7506 (6)	1.2040 (3)	0.04237 (17)	0.0437 (9)
C10	0.6312 (5)	1.3316 (3)	0.02430 (13)	0.0384 (8)
H1N	0.334 (7)	0.922 (3)	0.1111 (15)	0.0447*
H1O	0.722 (9)	1.470 (4)	−0.0157 (19)	0.0701*
H2	0.278 (7)	0.793 (4)	0.2003 (15)	0.0513*
H5	0.939 (8)	0.518 (4)	0.1166 (17)	0.0680*
H6	0.846 (7)	0.722 (4)	0.0777 (16)	0.0537*
H8A	0.489 (8)	1.153 (4)	0.1063 (16)	0.0527*
H8B	0.377 (8)	1.101 (3)	0.0478 (15)	0.0527*
H9A	0.899 (7)	1.225 (4)	0.0680 (16)	0.0523*
H9B	0.840 (7)	1.164 (4)	0.0077 (16)	0.0523*

	U11	U22	U33	U12	U13	U23
Cl1	0.1600 (13)	0.0566 (6)	0.0704 (7)	−0.0127 (7)	0.0418 (7)	0.0207 (5)
Cl2	0.1284 (11)	0.0363 (5)	0.1187 (10)	0.0107 (6)	−0.0093 (8)	0.0277 (5)
O1	0.0476 (13)	0.0356 (12)	0.0924 (19)	0.0084 (10)	0.0234 (12)	0.0257 (12)
O2	0.0400 (11)	0.0410 (12)	0.0846 (17)	0.0114 (9)	0.0176 (11)	0.0226 (11)
O3	0.0251 (10)	0.0418 (12)	0.0969 (18)	0.0059 (8)	0.0058 (10)	0.0219 (12)
N1	0.0260 (10)	0.0317 (12)	0.0541 (14)	0.0044 (9)	0.0040 (10)	0.0114 (10)
C1	0.0337 (13)	0.0263 (12)	0.0423 (14)	−0.0008 (10)	−0.0030 (10)	0.0043 (10)
C2	0.0540 (17)	0.0294 (13)	0.0449 (16)	−0.0031 (12)	0.0066 (13)	0.0006 (12)
C3	0.073 (2)	0.0331 (15)	0.0440 (16)	−0.0104 (14)	0.0021 (15)	0.0056 (12)
C4	0.072 (2)	0.0276 (14)	0.063 (2)	0.0001 (14)	−0.0119 (17)	0.0098 (14)
C5	0.059 (2)	0.0345 (16)	0.077 (2)	0.0123 (15)	0.0027 (18)	0.0006 (16)
C6	0.0445 (16)	0.0358 (15)	0.0542 (18)	0.0066 (12)	0.0086 (13)	0.0038 (13)
C7	0.0279 (12)	0.0302 (13)	0.0455 (14)	0.0028 (10)	0.0029 (10)	0.0078 (11)
C8	0.0307 (14)	0.0320 (14)	0.069 (2)	0.0075 (11)	0.0112 (13)	0.0165 (14)
C9	0.0319 (14)	0.0315 (14)	0.068 (2)	0.0042 (11)	0.0091 (13)	0.0137 (13)
C10	0.0305 (13)	0.0305 (13)	0.0543 (16)	0.0010 (10)	0.0021 (11)	0.0090 (12)

Cl1—C3	1.730 (4)	C4—C5	1.377 (5)
Cl2—C4	1.734 (3)	C5—C6	1.384 (5)
O1—C10	1.286 (4)	C7—C8	1.518 (4)
O2—C10	1.236 (3)	C8—C9	1.497 (5)
O3—C7	1.214 (3)	C9—C10	1.495 (4)
O1—H1O	0.80 (4)	C2—H2	0.96 (4)
N1—C1	1.414 (4)	C5—H5	0.98 (4)
N1—C7	1.346 (4)	C6—H6	0.88 (4)
N1—H1N	0.81 (3)	C8—H8A	0.90 (4)
C1—C6	1.382 (4)	C8—H8B	1.02 (4)
C1—C2	1.383 (4)	C9—H9A	0.94 (4)
C2—C3	1.382 (4)	C9—H9B	0.99 (4)
C3—C4	1.376 (5)
C10—O1—H1O	112 (3)	C8—C9—C10	114.0 (2)
C1—N1—C7	126.1 (2)	O1—C10—O2	123.3 (3)
C7—N1—H1N	117 (2)	O1—C10—C9	114.8 (2)
C1—N1—H1N	116 (2)	O2—C10—C9	121.9 (3)
N1—C1—C6	122.5 (3)	C1—C2—H2	119 (2)
N1—C1—C2	117.6 (3)	C3—C2—H2	121 (2)
C2—C1—C6	119.9 (3)	C4—C5—H5	119 (2)
C1—C2—C3	119.9 (3)	C6—C5—H5	121 (2)
Cl1—C3—C2	118.0 (3)	C1—C6—H6	121 (3)
C2—C3—C4	120.4 (3)	C5—C6—H6	120 (3)
Cl1—C3—C4	121.6 (3)	C7—C8—H8A	106 (3)
C3—C4—C5	119.7 (3)	C7—C8—H8B	110.2 (18)
Cl2—C4—C5	119.1 (3)	C9—C8—H8A	111 (3)
Cl2—C4—C3	121.2 (3)	C9—C8—H8B	112.2 (19)
C4—C5—C6	120.5 (3)	H8A—C8—H8B	104 (3)
C1—C6—C5	119.7 (3)	C8—C9—H9A	111 (2)
O3—C7—N1	123.5 (3)	C8—C9—H9B	114 (2)
O3—C7—C8	122.6 (3)	C10—C9—H9A	105 (2)
N1—C7—C8	113.9 (2)	C10—C9—H9B	109 (2)
C7—C8—C9	112.8 (2)	H9A—C9—H9B	104 (3)
C7—N1—C1—C2	140.0 (3)	Cl1—C3—C4—C5	−177.0 (3)
C7—N1—C1—C6	−42.4 (4)	C2—C3—C4—Cl2	−177.3 (3)
C1—N1—C7—O3	4.2 (5)	C2—C3—C4—C5	2.0 (5)
C1—N1—C7—C8	−175.8 (3)	Cl2—C4—C5—C6	178.1 (3)
N1—C1—C2—C3	177.7 (3)	C3—C4—C5—C6	−1.2 (6)
C6—C1—C2—C3	0.0 (5)	C4—C5—C6—C1	−0.2 (5)
N1—C1—C6—C5	−176.8 (3)	O3—C7—C8—C9	9.0 (5)
C2—C1—C6—C5	0.8 (5)	N1—C7—C8—C9	−171.0 (3)
C1—C2—C3—Cl1	177.6 (2)	C7—C8—C9—C10	−179.4 (3)
C1—C2—C3—C4	−1.4 (5)	C8—C9—C10—O1	−169.1 (3)
Cl1—C3—C4—Cl2	3.7 (5)	C8—C9—C10—O2	11.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.81 (3)	2.10 (3)	2.887 (3)	165 (3)
O1—H1O···O2ii	0.80 (4)	1.87 (4)	2.665 (3)	170 (4)
C6—H6···O3	0.88 (4)	2.58 (4)	2.960 (4)	107 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.81 (3)	2.10 (3)	2.887 (3)	165 (3)
O1—H1O⋯O2ii	0.80 (4)	1.87 (4)	2.665 (3)	170 (4)
C6—H6⋯O3	0.88 (4)	2.58 (4)	2.960 (4)	107 (3)

Symmetry codes: (i) ; (ii) .