3-[(3,5-Dichloro-anilino)carbon-yl]propionic acid.

In the crystal structure of the title compound, C(10)H(9)Cl(2)NO(3), the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to the H atoms of the adjacent -CH(2) groups. The C=O and O-H bonds of the acid group are in relatively rare anti positions with respect to each other. This is an obvious consequence of the concerted effects of both the all-anti mol-ecular conformation and the intermolecular hydrogen bond donated to the amide carbonyl group. In the crystal, mol-ecules are packed into infinite chains through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the effect of ring and side-chain substitutions on the structures of amide compounds, see: Gowda et al. (2009 ▶). For the packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 ▶). For the various modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶).

Experimental

Crystal data

C10H9Cl2NO3

M = 262.08

Monoclinic,

a = 7.350 (1) Å

b = 10.318 (2) Å

c = 15.031 (3) Å

β = 99.44 (2)°

V = 1124.5 (3) Å3

Z = 4

Cu Kα radiation

μ = 5.15 mm−1

T = 299 K

0.48 × 0.30 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.142, T max = 0.242

4204 measured reflections

2005 independent reflections

1794 reflections with I > 2σ(I)

R int = 0.111

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.170

S = 1.13

2005 reflections

151 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809010319/cs2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010319/cs2111Isup2.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	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.350 (1) Å	θ = 7.4–20.6°
b = 10.318 (2) Å	µ = 5.15 mm−1
c = 15.031 (3) Å	T = 299 K
β = 99.44 (2)°	Prism, colourless
V = 1124.5 (3) Å3	0.48 × 0.30 × 0.28 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.111
graphite	θmax = 67.1°, θmin = 5.2°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.142, Tmax = 0.242	l = −17→17
4204 measured reflections	3 standard reflections every 120 min
2005 independent reflections	intensity decay: 1.0%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0804P)2 + 0.4071P] where P = (Fo2 + 2Fc2)/3
2005 reflections	(Δ/σ)max = 0.009
151 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.54 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.2687 (3)	0.5234 (3)	0.51327 (16)	0.0360 (6)
C2	0.1971 (3)	0.4036 (3)	0.48363 (18)	0.0390 (6)
H2	0.1668	0.3863	0.4223	0.047*
C3	0.1715 (4)	0.3108 (3)	0.54585 (19)	0.0415 (6)
C4	0.2153 (4)	0.3313 (3)	0.63743 (19)	0.0453 (7)
H4	0.1971	0.2676	0.6789	0.054*
C5	0.2872 (4)	0.4502 (4)	0.66443 (18)	0.0453 (7)
C6	0.3155 (4)	0.5480 (3)	0.60551 (17)	0.0435 (7)
H6	0.3642	0.6276	0.6266	0.052*
C7	0.3499 (3)	0.7371 (3)	0.45487 (16)	0.0374 (6)
C8	0.3313 (4)	0.8125 (3)	0.36730 (17)	0.0421 (7)
H8A	0.3996	0.7685	0.3263	0.051*
H8B	0.2025	0.8148	0.3395	0.051*
C9	0.4014 (4)	0.9480 (3)	0.38180 (17)	0.0447 (7)
H9A	0.5322	0.9451	0.4055	0.054*
H9B	0.3400	0.9891	0.4268	0.054*
C10	0.3724 (4)	1.0293 (3)	0.29825 (18)	0.0436 (7)
N1	0.2863 (3)	0.6158 (3)	0.44600 (15)	0.0403 (6)
H1N	0.242 (4)	0.584 (4)	0.387 (3)	0.048*
O1	0.4152 (3)	0.7867 (3)	0.52683 (13)	0.0543 (6)
O2	0.4186 (4)	1.1531 (3)	0.30787 (14)	0.0622 (7)
H2O	0.459 (5)	1.167 (5)	0.3609 (15)	0.075*
O3	0.3114 (4)	0.9893 (3)	0.22424 (13)	0.0620 (7)
Cl1	0.07961 (12)	0.16217 (8)	0.50728 (6)	0.0580 (3)
Cl2	0.34909 (13)	0.47994 (11)	0.77952 (5)	0.0696 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (12)	0.0368 (17)	0.0252 (12)	0.0015 (11)	0.0026 (9)	0.0014 (11)
C2	0.0487 (13)	0.0390 (17)	0.0287 (12)	0.0004 (12)	0.0050 (10)	−0.0022 (11)
C3	0.0490 (13)	0.0379 (17)	0.0382 (14)	−0.0009 (12)	0.0089 (10)	−0.0034 (12)
C4	0.0589 (16)	0.044 (2)	0.0339 (14)	−0.0048 (13)	0.0098 (11)	0.0050 (12)
C5	0.0585 (15)	0.051 (2)	0.0265 (13)	−0.0048 (13)	0.0071 (10)	0.0019 (12)
C6	0.0590 (15)	0.0454 (19)	0.0254 (13)	−0.0089 (13)	0.0044 (10)	−0.0008 (12)
C7	0.0463 (12)	0.0401 (17)	0.0242 (11)	−0.0013 (12)	0.0007 (9)	0.0008 (11)
C8	0.0598 (15)	0.0408 (17)	0.0237 (12)	−0.0014 (13)	0.0007 (10)	0.0025 (11)
C9	0.0643 (15)	0.0440 (19)	0.0230 (12)	−0.0036 (14)	−0.0009 (10)	0.0038 (12)
C10	0.0611 (15)	0.0426 (18)	0.0252 (12)	−0.0021 (13)	0.0012 (10)	0.0043 (12)
N1	0.0602 (12)	0.0370 (15)	0.0220 (10)	−0.0033 (11)	0.0019 (8)	−0.0001 (9)
O1	0.0824 (13)	0.0483 (15)	0.0272 (10)	−0.0156 (11)	−0.0056 (9)	0.0019 (9)
O2	0.1047 (17)	0.0458 (15)	0.0289 (11)	−0.0123 (13)	−0.0107 (10)	0.0092 (10)
O3	0.1032 (17)	0.0545 (16)	0.0224 (10)	−0.0094 (13)	−0.0071 (10)	0.0031 (9)
Cl1	0.0808 (6)	0.0403 (6)	0.0533 (5)	−0.0134 (4)	0.0127 (4)	−0.0065 (3)
Cl2	0.1032 (7)	0.0795 (8)	0.0243 (4)	−0.0260 (5)	0.0056 (4)	0.0014 (3)

C1—C2	1.388 (4)	C7—N1	1.335 (4)
C1—C6	1.396 (4)	C7—C8	1.516 (4)
C1—N1	1.411 (4)	C8—C9	1.494 (5)
C2—C3	1.372 (4)	C8—H8A	0.97
C2—H2	0.93	C8—H8B	0.97
C3—C4	1.378 (4)	C9—C10	1.496 (4)
C3—Cl1	1.737 (3)	C9—H9A	0.97
C4—C5	1.371 (5)	C9—H9B	0.97
C4—H4	0.93	C10—O3	1.202 (4)
C5—C6	1.381 (4)	C10—O2	1.323 (4)
C5—Cl2	1.742 (3)	N1—H1N	0.95 (4)
C6—H6	0.93	O2—H2O	0.82 (2)
C7—O1	1.221 (3)
C2—C1—C6	120.0 (3)	N1—C7—C8	114.5 (2)
C2—C1—N1	116.5 (2)	C9—C8—C7	112.0 (2)
C6—C1—N1	123.5 (3)	C9—C8—H8A	109
C3—C2—C1	119.3 (2)	C7—C8—H8A	109
C3—C2—H2	120.3	C9—C8—H8B	109
C1—C2—H2	120.3	C7—C8—H8B	109
C2—C3—C4	122.6 (3)	H8A—C8—H8B	108
C2—C3—Cl1	118.5 (2)	C8—C9—C10	113.8 (2)
C4—C3—Cl1	118.9 (2)	C8—C9—H9A	109
C5—C4—C3	116.7 (3)	C10—C9—H9A	109
C5—C4—H4	121.7	C8—C9—H9B	109
C3—C4—H4	121.7	C10—C9—H9B	109
C4—C5—C6	123.7 (3)	H9A—C9—H9B	108
C4—C5—Cl2	118.5 (2)	O3—C10—O2	118.8 (3)
C6—C5—Cl2	117.8 (3)	O3—C10—C9	124.4 (3)
C5—C6—C1	117.7 (3)	O2—C10—C9	116.8 (3)
C5—C6—H6	121.1	C7—N1—C1	129.3 (2)
C1—C6—H6	121.1	C7—N1—H1N	118 (2)
O1—C7—N1	124.2 (3)	C1—N1—H1N	112 (2)
O1—C7—C8	121.3 (3)	C10—O2—H2O	109 (3)
O1—C7—C8—C9	0.2 (4)	O1—C7—N1—C1	4.3 (5)
N1—C7—C8—C9	178.9 (2)	C8—C7—N1—C1	−174.4 (3)
C7—C8—C9—C10	−175.5 (2)	C2—C1—N1—C7	180.0 (3)
C8—C9—C10—O3	−5.3 (5)	C6—C1—N1—C7	1.3 (4)
C8—C9—C10—O2	175.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.95 (4)	1.93 (4)	2.857 (3)	167 (3)
O2—H2O···O1ii	0.82 (2)	1.85 (2)	2.656 (3)	170 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.95 (4)	1.93 (4)	2.857 (3)	167 (3)
O2—H2O⋯O1ii	0.82 (2)	1.85 (2)	2.656 (3)	170 (4)

Symmetry codes: (i) ; (ii) .