3-(3,5-Dichloro-anilinocarbon-yl)propionic acid.

The crystal structure of the title compound, C(10)H(9)Cl(2)NO(3), consists of dimers due to inter-molecular O-H⋯O hydrogen bonding forming an R(2) (2)(8) ring through the carboxyl- groups. These dimers are linked to each other by inter-molecular hydrogen bonds between the amine group and the adjacent carbonyl O atom. A single C-Cl⋯π inter-action is also observed between the chloro-substituted aromatic rings.

Related literature

For related literature, see: Nath et al. (2001 ▶); Wardell et al. (2006 ▶).

Experimental

Crystal data

C10H9Cl2NO3

M = 262.08

Triclinic,

a = 4.8568 (2) Å

b = 8.6677 (4) Å

c = 13.9038 (8) Å

α = 74.467 (3)°

β = 80.495 (2)°

γ = 82.712 (3)°

V = 554.09 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 296 (2) K

0.25 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.870, T max = 0.945

12157 measured reflections

2971 independent reflections

2065 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.125

S = 1.07

2971 reflections

172 parameters

Only H-atom coordinates refined

Δρmax = 0.27 e Å−3

Δρmin = −0.43 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 (Farrugia, 1999) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008556/fj2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008556/fj2109Isup2.hkl

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

C10H9Cl2NO3	Z = 2
Mr = 262.08	F000 = 268
Triclinic, P1	Dx = 1.571 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.8568 (2) Å	Cell parameters from 2971 reflections
b = 8.6677 (4) Å	θ = 1.5–29.2º
c = 13.9038 (8) Å	µ = 0.58 mm−1
α = 74.467 (3)º	T = 296 (2) K
β = 80.495 (2)º	Needle, colourless
γ = 82.712 (3)º	0.25 × 0.12 × 0.10 mm
V = 554.09 (5) Å3

Bruker KappaAPEXII CCD diffractometer	2971 independent reflections
Radiation source: fine-focus sealed tube	2065 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
Detector resolution: 7.4 pixels mm-1	θmax = 29.2º
T = 296(2) K	θmin = 1.5º
ω scans	h = −6→6
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.870, Tmax = 0.945	l = −19→18
12157 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	Only H-atom coordinates refined
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.2158P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2971 reflections	Δρmax = 0.27 e Å−3
172 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	−0.50817 (12)	1.03658 (7)	0.31192 (6)	0.0754 (2)
Cl2	0.18783 (13)	0.70434 (7)	0.57110 (5)	0.0704 (2)
O1	0.1715 (4)	0.0213 (3)	0.07439 (17)	0.0910 (7)
H1	0.281 (8)	−0.046 (4)	0.039 (3)	0.109*
O2	0.5114 (3)	0.1840 (3)	0.01798 (15)	0.0829 (6)
O3	−0.1931 (3)	0.5285 (3)	0.18654 (16)	0.0814 (6)
N1	0.2023 (3)	0.5827 (3)	0.23147 (16)	0.0607 (5)
H1A	0.377 (6)	0.563 (3)	0.222 (2)	0.073*
C1	0.2819 (4)	0.1536 (4)	0.06543 (17)	0.0629 (7)
C2	0.1014 (4)	0.2656 (4)	0.1188 (2)	0.0636 (7)
H2A	−0.054 (6)	0.295 (3)	0.089 (2)	0.076*
H2B	0.031 (6)	0.202 (3)	0.186 (2)	0.076*
C3	0.2413 (4)	0.4095 (4)	0.1194 (2)	0.0653 (7)
H3A	0.413 (6)	0.381 (3)	0.139 (2)	0.078*
H3B	0.275 (6)	0.480 (3)	0.051 (2)	0.078*
C4	0.0626 (4)	0.5118 (3)	0.18182 (18)	0.0588 (6)
C5	0.0789 (4)	0.6763 (3)	0.29919 (18)	0.0525 (5)
C6	−0.1369 (4)	0.7959 (3)	0.2744 (2)	0.0558 (5)
H6	−0.196 (5)	0.813 (3)	0.208 (2)	0.067*
C7	−0.2454 (4)	0.8838 (2)	0.3433 (2)	0.0556 (6)
C8	−0.1529 (4)	0.8582 (2)	0.4348 (2)	0.0565 (6)
H8	−0.234 (6)	0.918 (3)	0.4805 (19)	0.068*
C9	0.0627 (4)	0.7390 (2)	0.45673 (19)	0.0529 (5)
C10	0.1799 (4)	0.6482 (2)	0.39000 (19)	0.0534 (5)
H10	0.323 (5)	0.569 (3)	0.4041 (18)	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.0467 (3)	0.0511 (3)	0.1229 (6)	0.0104 (2)	−0.0224 (3)	−0.0129 (3)
Cl2	0.0688 (4)	0.0548 (3)	0.0942 (5)	−0.0021 (3)	−0.0275 (3)	−0.0220 (3)
O1	0.0561 (10)	0.1287 (19)	0.1042 (16)	−0.0241 (11)	0.0243 (10)	−0.0704 (14)
O2	0.0471 (9)	0.1186 (16)	0.0902 (13)	−0.0130 (9)	0.0204 (9)	−0.0543 (12)
O3	0.0227 (6)	0.1166 (16)	0.1185 (15)	0.0053 (8)	−0.0064 (8)	−0.0601 (13)
N1	0.0212 (7)	0.0772 (13)	0.0841 (14)	0.0006 (7)	−0.0002 (7)	−0.0273 (11)
C1	0.0344 (9)	0.110 (2)	0.0533 (13)	−0.0055 (11)	−0.0032 (9)	−0.0381 (13)
C2	0.0293 (9)	0.104 (2)	0.0631 (15)	−0.0026 (10)	−0.0004 (9)	−0.0360 (14)
C3	0.0273 (9)	0.0925 (19)	0.0749 (16)	0.0001 (10)	0.0053 (9)	−0.0290 (14)
C4	0.0240 (8)	0.0786 (15)	0.0716 (15)	−0.0001 (8)	−0.0007 (8)	−0.0208 (12)
C5	0.0242 (7)	0.0512 (11)	0.0789 (15)	−0.0053 (7)	0.0001 (8)	−0.0146 (10)
C6	0.0306 (8)	0.0564 (13)	0.0747 (15)	−0.0046 (8)	−0.0058 (9)	−0.0074 (11)
C7	0.0301 (8)	0.0381 (10)	0.0934 (17)	−0.0015 (7)	−0.0078 (9)	−0.0086 (10)
C8	0.0404 (10)	0.0379 (11)	0.0926 (18)	−0.0046 (8)	−0.0083 (10)	−0.0187 (11)
C9	0.0406 (9)	0.0367 (10)	0.0822 (15)	−0.0072 (8)	−0.0133 (9)	−0.0118 (10)
C10	0.0337 (9)	0.0388 (10)	0.0864 (17)	−0.0017 (7)	−0.0114 (9)	−0.0125 (10)

Cl1—C7	1.737 (2)	C3—C4	1.503 (3)
Cl2—C9	1.734 (2)	C3—H3A	0.91 (3)
O1—C1	1.295 (3)	C3—H3B	0.99 (3)
O1—H1	0.92 (4)	C5—C10	1.380 (3)
O2—C1	1.219 (3)	C5—C6	1.394 (3)
O3—C4	1.225 (2)	C6—C7	1.378 (3)
N1—C4	1.343 (3)	C6—H6	0.98 (3)
N1—C5	1.415 (3)	C7—C8	1.372 (3)
N1—H1A	0.84 (3)	C8—C9	1.386 (3)
C1—C2	1.488 (3)	C8—H8	0.93 (3)
C2—C3	1.497 (4)	C9—C10	1.381 (3)
C2—H2A	0.90 (3)	C10—H10	0.92 (3)
C2—H2B	0.97 (3)
C1—O1—H1	113 (2)	O3—C4—C3	121.8 (2)
C4—N1—C5	125.67 (16)	N1—C4—C3	115.51 (17)
C4—N1—H1A	114.4 (19)	C10—C5—C6	120.6 (2)
C5—N1—H1A	119.8 (19)	C10—C5—N1	118.47 (19)
O2—C1—O1	123.4 (2)	C6—C5—N1	121.0 (2)
O2—C1—C2	123.1 (3)	C7—C6—C5	118.0 (2)
O1—C1—C2	113.5 (2)	C7—C6—H6	124.9 (15)
C1—C2—C3	113.79 (18)	C5—C6—H6	117.1 (15)
C1—C2—H2A	107.1 (18)	C8—C7—C6	123.18 (19)
C3—C2—H2A	111.1 (18)	C8—C7—Cl1	118.42 (18)
C1—C2—H2B	107.3 (16)	C6—C7—Cl1	118.39 (19)
C3—C2—H2B	114.0 (16)	C7—C8—C9	117.3 (2)
H2A—C2—H2B	103 (2)	C7—C8—H8	121.1 (17)
C2—C3—C4	112.22 (18)	C9—C8—H8	121.6 (17)
C2—C3—H3A	111.7 (18)	C10—C9—C8	121.8 (2)
C4—C3—H3A	111.0 (17)	C10—C9—Cl2	119.54 (16)
C2—C3—H3B	110.6 (17)	C8—C9—Cl2	118.68 (19)
C4—C3—H3B	105.7 (17)	C5—C10—C9	119.2 (2)
H3A—C3—H3B	105 (2)	C5—C10—H10	118.7 (16)
O3—C4—N1	122.7 (2)	C9—C10—H10	122.1 (16)
O2—C1—C2—C3	−7.0 (4)	C5—C6—C7—C8	−0.6 (3)
O1—C1—C2—C3	172.9 (2)	C5—C6—C7—Cl1	178.35 (15)
C1—C2—C3—C4	−174.8 (2)	C6—C7—C8—C9	0.9 (3)
C5—N1—C4—O3	4.0 (4)	Cl1—C7—C8—C9	−178.06 (14)
C5—N1—C4—C3	−176.1 (2)	C7—C8—C9—C10	−0.4 (3)
C2—C3—C4—O3	−34.9 (4)	C7—C8—C9—Cl2	179.37 (15)
C2—C3—C4—N1	145.1 (2)	C6—C5—C10—C9	0.6 (3)
C4—N1—C5—C10	133.9 (2)	N1—C5—C10—C9	179.70 (17)
C4—N1—C5—C6	−47.0 (3)	C8—C9—C10—C5	−0.3 (3)
C10—C5—C6—C7	−0.2 (3)	Cl2—C9—C10—C5	179.91 (15)
N1—C5—C6—C7	−179.26 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.84 (3)	2.07 (3)	2.904 (2)	175 (2)
O1—H1···O2ii	0.92 (4)	1.74 (4)	2.658 (3)	175 (4)
C7—Cl1···Cgiii	1.737 (2)	3.5398 (11)	4.033 (2)	93.34 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.84 (3)	2.07 (3)	2.904 (2)	175 (2)
O1—H1⋯O2ii	0.92 (4)	1.74 (4)	2.658 (3)	175 (4)
C7—Cl1⋯Cgiii	1.74 (1)	3.54 (1)	4.033 (2)	93 (1)

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of atoms C5–C10.