N-(2,5-Dichloro-phen-yl)succinamic acid.

In the title compound, C(10)H(9)Cl(2)NO(3), the conformation of the N-H bond in the amide segment is syn with respect to the ortho-Cl atom and anti to the meta-Cl atom of the benzene ring. In the crystal, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds pack the mol-ecules into two types of chains along the a and b axes, respectively, leading to an overall sheet structure. The acid group in the side chain is disordered and was refined using a split model with site-occupation factors of 0.60:0.40.

Related literature

For our studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2007 ▶); Saraswathi et al. (2011 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶) and on N-chloro-aryl­sulfonamides, see: Gowda et al. (2003 ▶). For the modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). For the packing of mol­ecules involving dimeric hydrogen-bonding associations of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C10H9Cl2NO3

M = 262.08

Monoclinic,

a = 5.726 (1) Å

b = 4.787 (1) Å

c = 41.583 (6) Å

β = 91.93 (2)°

V = 1139.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 293 K

0.44 × 0.16 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.791, T max = 0.951

3375 measured reflections

2046 independent reflections

1552 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.171

S = 1.14

2046 reflections

185 parameters

54 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.75 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablock(s) I, global. DOI: 10.1107/S1600536811028297/vm2110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028297/vm2110Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028297/vm2110Isup3.cml

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

C10H9Cl2NO3	F(000) = 536
Mr = 262.08	Dx = 1.528 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 987 reflections
a = 5.726 (1) Å	θ = 2.9–27.7°
b = 4.787 (1) Å	µ = 0.56 mm−1
c = 41.583 (6) Å	T = 293 K
β = 91.93 (2)°	Needle, colourless
V = 1139.2 (4) Å3	0.44 × 0.16 × 0.09 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2046 independent reflections
Radiation source: fine-focus sealed tube	1552 reflections with I > 2σ(I)
graphite	Rint = 0.022
Rotation method data acquisition using ω scans	θmax = 25.3°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→6
Tmin = 0.791, Tmax = 0.951	k = −5→2
3375 measured reflections	l = −50→37

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0436P)2 + 4.544P] where P = (Fo2 + 2Fc2)/3
2046 reflections	(Δ/σ)max = 0.048
185 parameters	Δρmax = 0.75 e Å−3
54 restraints	Δρmin = −0.41 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 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	Occ. (<1)
Cl1	0.3416 (2)	−0.1995 (3)	0.13931 (4)	0.0513 (4)
Cl2	0.8927 (3)	0.6671 (3)	0.22318 (3)	0.0460 (4)
O1	0.8848 (9)	0.5091 (8)	0.10285 (10)	0.0599 (13)
O2A	1.4182 (19)	−0.004 (3)	0.0382 (2)	0.088 (4)	0.60
H2A	1.4940	−0.0747	0.0239	0.106*	0.60
O2B	1.325 (3)	−0.072 (3)	0.0293 (4)	0.061 (4)	0.40
H2B	1.3972	−0.1171	0.0134	0.074*	0.40
O3A	1.259 (2)	0.248 (3)	−0.0021 (3)	0.082 (4)	0.60
O3B	1.357 (4)	0.322 (4)	0.0053 (5)	0.096 (7)	0.40
N1	0.7824 (8)	0.0816 (9)	0.12040 (10)	0.0342 (10)
H1N	0.791 (9)	−0.091 (5)	0.1164 (13)	0.041*
C1	0.6994 (8)	0.1621 (10)	0.15067 (11)	0.0296 (11)
C2	0.4967 (9)	0.0438 (11)	0.16233 (12)	0.0342 (12)
C3	0.4144 (9)	0.1202 (12)	0.19205 (13)	0.0402 (13)
H3	0.2780	0.0402	0.1994	0.048*
C4	0.5332 (9)	0.3132 (12)	0.21069 (13)	0.0412 (13)
H4	0.4777	0.3662	0.2305	0.049*
C5	0.7367 (9)	0.4276 (11)	0.19951 (12)	0.0334 (12)
C6	0.8201 (8)	0.3543 (11)	0.17001 (11)	0.0321 (12)
H6	0.9576	0.4337	0.1630	0.039*
C7	0.8798 (10)	0.2569 (11)	0.09932 (13)	0.0369 (13)
C8	0.9872 (12)	0.1158 (13)	0.07101 (14)	0.0516 (16)
H8A	1.1120	−0.0047	0.0791	0.062*
H8B	0.8695	−0.0031	0.0608	0.062*
C9A	1.082 (2)	0.297 (3)	0.0464 (2)	0.044 (3)	0.60
H9A	1.1601	0.4541	0.0568	0.053*	0.60
H9B	0.9545	0.3688	0.0329	0.053*	0.60
C9B	1.172 (3)	0.293 (5)	0.0582 (5)	0.058 (5)	0.40
H9C	1.2859	0.3277	0.0756	0.069*	0.40
H9D	1.1028	0.4709	0.0523	0.069*	0.40
C10A	1.253 (3)	0.145 (3)	0.0256 (4)	0.057 (4)	0.60
C10B	1.302 (4)	0.187 (4)	0.0298 (5)	0.043 (6)	0.40

	U11	U22	U33	U12	U13	U23
Cl1	0.0426 (8)	0.0500 (9)	0.0613 (9)	−0.0162 (7)	0.0020 (7)	−0.0020 (8)
Cl2	0.0553 (9)	0.0455 (8)	0.0376 (7)	−0.0051 (7)	0.0053 (6)	−0.0069 (7)
O1	0.106 (4)	0.026 (2)	0.050 (3)	−0.007 (2)	0.040 (2)	−0.0065 (19)
O2A	0.092 (7)	0.118 (8)	0.055 (5)	0.027 (6)	0.018 (5)	−0.009 (5)
O2B	0.068 (6)	0.056 (5)	0.062 (6)	0.002 (4)	0.031 (4)	−0.004 (4)
O3A	0.075 (6)	0.109 (8)	0.065 (6)	0.019 (6)	0.017 (5)	−0.005 (6)
O3B	0.110 (10)	0.081 (9)	0.099 (10)	0.001 (8)	0.038 (8)	0.009 (8)
N1	0.044 (2)	0.024 (2)	0.037 (2)	−0.004 (2)	0.0166 (19)	−0.004 (2)
C1	0.029 (2)	0.025 (3)	0.035 (3)	0.003 (2)	0.011 (2)	0.001 (2)
C2	0.031 (3)	0.030 (3)	0.042 (3)	−0.003 (2)	0.005 (2)	0.001 (2)
C3	0.032 (3)	0.045 (3)	0.044 (3)	−0.003 (3)	0.016 (2)	0.008 (3)
C4	0.042 (3)	0.046 (3)	0.037 (3)	0.004 (3)	0.020 (2)	0.005 (3)
C5	0.037 (3)	0.031 (3)	0.032 (3)	0.004 (2)	0.007 (2)	0.002 (2)
C6	0.028 (3)	0.033 (3)	0.037 (3)	−0.001 (2)	0.013 (2)	0.005 (2)
C7	0.050 (3)	0.026 (3)	0.035 (3)	−0.002 (2)	0.012 (2)	−0.006 (2)
C8	0.069 (4)	0.043 (3)	0.045 (3)	−0.007 (3)	0.027 (3)	−0.012 (3)
C9A	0.062 (6)	0.039 (5)	0.032 (5)	0.007 (5)	0.013 (4)	0.002 (5)
C9B	0.064 (9)	0.050 (8)	0.061 (9)	−0.001 (8)	0.018 (7)	−0.011 (8)
C10A	0.061 (7)	0.041 (7)	0.073 (8)	−0.009 (5)	0.043 (6)	0.002 (6)
C10B	0.048 (8)	0.037 (8)	0.045 (7)	−0.001 (5)	0.009 (4)	−0.004 (5)

Cl1—C2	1.733 (5)	C3—H3	0.9300
Cl2—C5	1.739 (5)	C4—C5	1.382 (7)
O1—C7	1.217 (6)	C4—H4	0.9300
O2A—C10A	1.282 (15)	C5—C6	1.377 (7)
O2A—H2A	0.8200	C6—H6	0.9300
O2B—C10B	1.246 (17)	C7—C8	1.507 (7)
O2B—H2B	0.8200	C8—C9A	1.458 (12)
O3A—C10A	1.254 (12)	C8—C9B	1.47 (2)
O3B—C10B	1.256 (15)	C8—H8A	0.9700
N1—C7	1.348 (7)	C8—H8B	0.9700
N1—C1	1.414 (6)	C9A—C10A	1.516 (12)
N1—H1N	0.85 (2)	C9A—H9A	0.9700
C1—C6	1.391 (7)	C9A—H9B	0.9700
C1—C2	1.393 (7)	C9B—C10B	1.505 (16)
C2—C3	1.386 (7)	C9B—H9C	0.9700
C3—C4	1.372 (8)	C9B—H9D	0.9700
C10A—O2A—H2A	109.5	C9A—C8—C7	117.0 (6)
C10B—O2B—H2B	109.5	C9B—C8—C7	110.1 (8)
C7—N1—C1	124.6 (4)	C9A—C8—H8A	108.1
C7—N1—H1N	117 (4)	C9B—C8—H8A	86.4
C1—N1—H1N	118 (4)	C7—C8—H8A	108.1
C6—C1—C2	118.1 (4)	C9A—C8—H8B	108.1
C6—C1—N1	121.3 (4)	C9B—C8—H8B	132.7
C2—C1—N1	120.5 (4)	C7—C8—H8B	108.1
C3—C2—C1	121.0 (5)	H8A—C8—H8B	107.3
C3—C2—Cl1	119.1 (4)	C8—C9A—C10A	112.3 (10)
C1—C2—Cl1	119.9 (4)	C8—C9A—H9A	109.1
C4—C3—C2	120.3 (5)	C10A—C9A—H9A	109.1
C4—C3—H3	119.8	C8—C9A—H9B	109.1
C2—C3—H3	119.8	C10A—C9A—H9B	109.1
C3—C4—C5	119.0 (5)	H9A—C9A—H9B	107.9
C3—C4—H4	120.5	C8—C9B—C10B	118.2 (17)
C5—C4—H4	120.5	C8—C9B—H9C	107.8
C6—C5—C4	121.4 (5)	C10B—C9B—H9C	107.7
C6—C5—Cl2	119.1 (4)	C8—C9B—H9D	107.8
C4—C5—Cl2	119.6 (4)	C10B—C9B—H9D	107.8
C5—C6—C1	120.2 (4)	H9C—C9B—H9D	107.1
C5—C6—H6	119.9	O3A—C10A—O2A	123.5 (12)
C1—C6—H6	119.9	O3A—C10A—C9A	112.0 (11)
O1—C7—N1	123.3 (5)	O2A—C10A—C9A	121.0 (14)
O1—C7—C8	122.0 (5)	O2B—C10B—O3B	117.8 (19)
N1—C7—C8	114.7 (5)	O2B—C10B—C9B	113.7 (18)
C9A—C8—C9B	27.7 (8)	O3B—C10B—C9B	127.6 (18)
C7—N1—C1—C6	−39.9 (8)	C1—N1—C7—O1	−7.7 (9)
C7—N1—C1—C2	142.0 (5)	C1—N1—C7—C8	171.2 (5)
C6—C1—C2—C3	1.5 (8)	O1—C7—C8—C9A	−4.8 (11)
N1—C1—C2—C3	179.7 (5)	N1—C7—C8—C9A	176.2 (7)
C6—C1—C2—Cl1	−179.4 (4)	O1—C7—C8—C9B	24.5 (13)
N1—C1—C2—Cl1	−1.2 (7)	N1—C7—C8—C9B	−154.4 (10)
C1—C2—C3—C4	−0.6 (8)	C9B—C8—C9A—C10A	79 (2)
Cl1—C2—C3—C4	−179.7 (4)	C7—C8—C9A—C10A	160.8 (11)
C2—C3—C4—C5	−0.6 (8)	C9A—C8—C9B—C10B	−70 (2)
C3—C4—C5—C6	0.8 (8)	C7—C8—C9B—C10B	179.8 (15)
C3—C4—C5—Cl2	−178.7 (4)	C8—C9A—C10A—O3A	152.1 (15)
C4—C5—C6—C1	0.1 (8)	C8—C9A—C10A—O2A	−48 (2)
Cl2—C5—C6—C1	179.7 (4)	C8—C9B—C10B—O2B	−33 (3)
C2—C1—C6—C5	−1.3 (7)	C8—C9B—C10B—O3B	136 (3)
N1—C1—C6—C5	−179.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O3Ai	0.82	1.90	2.687 (15)	162.
O2B—H2B···O3Bi	0.82	1.90	2.64 (2)	150.
N1—H1N···O1ii	0.85 (2)	2.07 (2)	2.901 (6)	167 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯O3Ai	0.82	1.90	2.687 (15)	162
O2B—H2B⋯O3Bi	0.82	1.90	2.64 (2)	150
N1—H1N⋯O1ii	0.85 (2)	2.07 (2)	2.901 (6)	167 (5)

Symmetry codes: (i) ; (ii) .