N-(2-Chloro-5-methyl-phen-yl)succinamic acid.

In the title compound, C(11)H(12)ClNO(3), the conformation of the N-H bond in the amide segment is syn with respect to the ortho-Cl atom. The amide and carboxyl C=O groups are syn to each other. Furthermore, the C=O and O-H bonds of the carboxyl group are in syn positions with respect to each other. The dihedral angle between the benzene ring and the amide group is 47.8 (2)°. In the crystal, mol-ecules are connected by pairs of O-H⋯O hydrogen bonds, forming inversion dimers. The dimers are further linked by N-H⋯O hydrogen bonds into double chains along the b-axis direction.

Related literature

For our previous studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-n class="Chemical">amides, see: Gowda et al. (2001 ▶); Saraswathi et al. (2011 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶). For modes of hydrogen bonding in the structures of carb­oxy­lic acids, see: Leiserowitz (1976 ▶). For the centrosymmetrical dimeric hydrogen-bonding association of carb­oxy­lic groups, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C11H12ClNO3

M = 241.67

Monoclinic,

a = 23.780 (5) Å

b = 4.7784 (7) Å

c = 23.892 (5) Å

β = 121.20 (1)°

V = 2322.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.42 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.877, T max = 0.975

4399 measured reflections

2322 independent reflections

1680 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.128

S = 1.19

2322 reflections

152 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">RED (Oxford Diffraction, 2009 ▶); 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/S1600536811054638/yk2035sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054638/yk2035Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811054638/yk2035Isup3.cml

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

C11H12ClNO3	F(000) = 1008
Mr = 241.67	Dx = 1.382 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1604 reflections
a = 23.780 (5) Å	θ = 2.6–27.9°
b = 4.7784 (7) Å	µ = 0.32 mm−1
c = 23.892 (5) Å	T = 293 K
β = 121.20 (1)°	Rod, colourless
V = 2322.2 (8) Å3	0.42 × 0.10 × 0.08 mm
Z = 8

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer	2322 independent reflections
Radiation source: fine-focus sealed tube	1680 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω and φ scans	θmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −29→28
Tmin = 0.877, Tmax = 0.975	k = −4→5
4399 measured reflections	l = −20→29

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ2(Fo2) + (0.0268P)2 + 6.3165P] where P = (Fo2 + 2Fc2)/3
2322 reflections	(Δ/σ)max = 0.044
152 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.14042 (4)	1.47549 (19)	0.23661 (4)	0.0481 (3)
O1	−0.02815 (14)	0.7770 (5)	0.14193 (17)	0.0703 (9)
O2	−0.18862 (14)	0.9786 (7)	0.03462 (14)	0.0749 (9)
O3	−0.21661 (15)	0.6674 (7)	0.08465 (14)	0.0783 (10)
H3O	−0.2438 (19)	0.623 (10)	0.0462 (12)	0.094*
N1	0.01311 (13)	1.2030 (5)	0.14261 (14)	0.0363 (6)
H1N	0.0095 (16)	1.378 (4)	0.1481 (16)	0.044*
C1	0.06702 (14)	1.1156 (6)	0.13712 (15)	0.0330 (7)
C2	0.12917 (15)	1.2274 (7)	0.17838 (15)	0.0362 (7)
C3	0.18210 (16)	1.1446 (8)	0.17339 (18)	0.0473 (9)
H3	0.2235	1.2205	0.2011	0.057*
C4	0.17314 (17)	0.9488 (8)	0.12704 (18)	0.0487 (9)
H4	0.2090	0.8916	0.1243	0.058*
C5	0.11180 (17)	0.8360 (7)	0.08458 (17)	0.0423 (8)
C6	0.05926 (15)	0.9222 (7)	0.09027 (16)	0.0377 (8)
H6	0.0177	0.8484	0.0620	0.045*
C7	−0.03027 (15)	1.0299 (7)	0.14512 (16)	0.0377 (7)
C8	−0.08153 (15)	1.1768 (7)	0.15378 (18)	0.0418 (8)
H8A	−0.1036	1.3159	0.1196	0.050*
H8B	−0.0599	1.2737	0.1955	0.050*
C9	−0.13225 (16)	0.9767 (8)	0.15140 (17)	0.0452 (8)
H9A	−0.1096	0.8164	0.1788	0.054*
H9B	−0.1553	1.0697	0.1698	0.054*
C10	−0.18136 (16)	0.8754 (8)	0.08466 (19)	0.0450 (9)
C11	0.1020 (2)	0.6300 (8)	0.03259 (19)	0.0605 (11)
H11A	0.1074	0.4431	0.0494	0.073*
H11B	0.1339	0.6646	0.0201	0.073*
H11C	0.0586	0.6509	−0.0049	0.073*

	U11	U22	U33	U12	U13	U23
Cl1	0.0457 (5)	0.0473 (5)	0.0465 (5)	−0.0107 (4)	0.0206 (4)	−0.0069 (4)
O1	0.0751 (19)	0.0230 (14)	0.147 (3)	−0.0019 (13)	0.081 (2)	−0.0023 (16)
O2	0.0717 (18)	0.081 (2)	0.0607 (17)	−0.0415 (17)	0.0259 (15)	−0.0011 (17)
O3	0.072 (2)	0.084 (2)	0.0667 (19)	−0.0466 (18)	0.0269 (16)	−0.0004 (18)
N1	0.0339 (13)	0.0231 (13)	0.0559 (17)	−0.0001 (12)	0.0261 (13)	−0.0033 (13)
C1	0.0331 (16)	0.0245 (16)	0.0432 (18)	0.0027 (13)	0.0210 (14)	0.0072 (14)
C2	0.0366 (16)	0.0327 (18)	0.0381 (17)	−0.0027 (14)	0.0185 (14)	0.0039 (15)
C3	0.0334 (17)	0.053 (2)	0.055 (2)	−0.0001 (16)	0.0220 (16)	0.0081 (19)
C4	0.0430 (19)	0.052 (2)	0.061 (2)	0.0101 (18)	0.0338 (18)	0.012 (2)
C5	0.056 (2)	0.0349 (19)	0.0450 (19)	0.0061 (16)	0.0326 (17)	0.0065 (16)
C6	0.0382 (17)	0.0322 (18)	0.0430 (18)	0.0004 (14)	0.0212 (14)	0.0030 (15)
C7	0.0319 (16)	0.0283 (18)	0.0519 (19)	−0.0012 (14)	0.0210 (14)	0.0002 (16)
C8	0.0342 (16)	0.0336 (19)	0.059 (2)	−0.0058 (15)	0.0254 (16)	−0.0103 (17)
C9	0.0421 (18)	0.045 (2)	0.060 (2)	−0.0081 (17)	0.0346 (17)	−0.0092 (18)
C10	0.0332 (17)	0.040 (2)	0.065 (2)	−0.0062 (15)	0.0281 (17)	0.0000 (18)
C11	0.080 (3)	0.052 (2)	0.064 (3)	0.011 (2)	0.047 (2)	0.004 (2)

Cl1—C2	1.740 (3)	C4—H4	0.9300
O1—C7	1.214 (4)	C5—C6	1.387 (4)
O2—C10	1.220 (4)	C5—C11	1.506 (5)
O3—C10	1.300 (4)	C6—H6	0.9300
O3—H3O	0.832 (19)	C7—C8	1.511 (4)
N1—C7	1.347 (4)	C8—C9	1.517 (4)
N1—C1	1.418 (4)	C8—H8A	0.9700
N1—H1N	0.858 (18)	C8—H8B	0.9700
C1—C6	1.388 (4)	C9—C10	1.487 (5)
C1—C2	1.390 (4)	C9—H9A	0.9700
C2—C3	1.382 (4)	C9—H9B	0.9700
C3—C4	1.379 (5)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.384 (5)	C11—H11C	0.9600
C10—O3—H3O	109 (4)	O1—C7—C8	122.3 (3)
C7—N1—C1	125.0 (3)	N1—C7—C8	114.3 (3)
C7—N1—H1N	117 (2)	C7—C8—C9	112.6 (3)
C1—N1—H1N	118 (2)	C7—C8—H8A	109.1
C6—C1—C2	118.4 (3)	C9—C8—H8A	109.1
C6—C1—N1	121.5 (3)	C7—C8—H8B	109.1
C2—C1—N1	120.1 (3)	C9—C8—H8B	109.1
C3—C2—C1	120.7 (3)	H8A—C8—H8B	107.8
C3—C2—Cl1	119.6 (3)	C10—C9—C8	114.4 (3)
C1—C2—Cl1	119.7 (2)	C10—C9—H9A	108.7
C4—C3—C2	119.6 (3)	C8—C9—H9A	108.7
C4—C3—H3	120.2	C10—C9—H9B	108.7
C2—C3—H3	120.2	C8—C9—H9B	108.7
C3—C4—C5	121.2 (3)	H9A—C9—H9B	107.6
C3—C4—H4	119.4	O2—C10—O3	123.0 (4)
C5—C4—H4	119.4	O2—C10—C9	123.6 (3)
C4—C5—C6	118.3 (3)	O3—C10—C9	113.4 (3)
C4—C5—C11	120.9 (3)	C5—C11—H11A	109.5
C6—C5—C11	120.9 (3)	C5—C11—H11B	109.5
C5—C6—C1	121.8 (3)	H11A—C11—H11B	109.5
C5—C6—H6	119.1	C5—C11—H11C	109.5
C1—C6—H6	119.1	H11A—C11—H11C	109.5
O1—C7—N1	123.4 (3)	H11B—C11—H11C	109.5
C7—N1—C1—C6	49.1 (5)	C4—C5—C6—C1	−0.2 (5)
C7—N1—C1—C2	−132.0 (3)	C11—C5—C6—C1	−178.8 (3)
C6—C1—C2—C3	−0.9 (5)	C2—C1—C6—C5	1.0 (5)
N1—C1—C2—C3	−179.8 (3)	N1—C1—C6—C5	179.9 (3)
C6—C1—C2—Cl1	178.8 (2)	C1—N1—C7—O1	−1.1 (6)
N1—C1—C2—Cl1	−0.2 (4)	C1—N1—C7—C8	177.6 (3)
C1—C2—C3—C4	−0.1 (5)	O1—C7—C8—C9	−5.4 (5)
Cl1—C2—C3—C4	−179.7 (3)	N1—C7—C8—C9	175.8 (3)
C2—C3—C4—C5	1.0 (5)	C7—C8—C9—C10	−75.1 (4)
C3—C4—C5—C6	−0.8 (5)	C8—C9—C10—O2	−12.7 (5)
C3—C4—C5—C11	177.8 (3)	C8—C9—C10—O3	168.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.83 (2)	1.83 (2)	2.652 (4)	172 (5)
N1—H1N···O1ii	0.86 (2)	2.08 (2)	2.910 (4)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.83 (2)	1.83 (2)	2.652 (4)	172 (5)
N1—H1N⋯O1ii	0.86 (2)	2.08 (2)	2.910 (4)	163 (3)

Symmetry codes: (i) ; (ii) .