N-(3-Chloro-2-methyl-phen-yl)succinamic acid.

In the title compound, C(11)H(12)ClNO(3), the dihedral angle between the benzene ring and the amide group is 44.9 (2)°. In the crystal, mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds. These dimers are further linked into sheets parallel to (013) via N-H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Chaithanya et al. (2012 ▶), of N-chloro­aryl­amides, see: Gowda & Rao (1989 ▶); Jyothi & Gowda (2004 ▶) and N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶), Usha & Gowda (2006 ▶).

Experimental

Crystal data

C11H12ClNO3

M = 241.67

Triclinic,

a = 4.7672 (9) Å

b = 6.297 (1) Å

c = 19.135 (3) Å

α = 87.24 (1)°

β = 83.95 (1)°

γ = 88.28 (2)°

V = 570.37 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.40 × 0.20 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.881, T max = 0.994

3270 measured reflections

2072 independent reflections

1578 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.127

S = 1.20

2072 reflections

152 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.24 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/S1600536812022763/bt5924sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022763/bt5924Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022763/bt5924Isup3.cml

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

C11H12ClNO3	Z = 2
Mr = 241.67	F(000) = 252
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7672 (9) Å	Cell parameters from 1394 reflections
b = 6.297 (1) Å	θ = 3.2–27.9°
c = 19.135 (3) Å	µ = 0.33 mm−1
α = 87.24 (1)°	T = 293 K
β = 83.95 (1)°	Plate, colourless
γ = 88.28 (2)°	0.40 × 0.20 × 0.02 mm
V = 570.37 (17) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2072 independent reflections
Radiation source: fine-focus sealed tube	1578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→5
Tmin = 0.881, Tmax = 0.994	k = −7→7
3270 measured reflections	l = −22→22

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ2(Fo2) + (0.0209P)2 + 0.6764P] where P = (Fo2 + 2Fc2)/3
2072 reflections	(Δ/σ)max = 0.004
152 parameters	Δρmax = 0.29 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.7008 (3)	1.2310 (2)	0.02839 (6)	0.0864 (4)
O1	0.0716 (4)	0.7206 (4)	0.30679 (13)	0.0603 (7)
O2	0.5808 (6)	0.1513 (5)	0.42666 (16)	0.0873 (11)
O3	0.2228 (7)	0.1937 (5)	0.50625 (15)	0.0877 (11)
H3O	0.286 (10)	0.084 (5)	0.525 (2)	0.105*
N1	0.5099 (5)	0.8278 (4)	0.26805 (14)	0.0415 (7)
H1N	0.682 (4)	0.810 (5)	0.2711 (17)	0.050*
C1	0.4362 (6)	0.9970 (5)	0.22052 (16)	0.0393 (7)
C2	0.5859 (6)	1.0149 (5)	0.15377 (16)	0.0406 (8)
C3	0.5154 (7)	1.1899 (6)	0.11106 (18)	0.0514 (9)
C4	0.3030 (8)	1.3342 (6)	0.1311 (2)	0.0613 (10)
H4	0.2607	1.4479	0.1009	0.074*
C5	0.1540 (8)	1.3084 (6)	0.1963 (2)	0.0607 (10)
H5	0.0081	1.4037	0.2101	0.073*
C6	0.2212 (7)	1.1408 (5)	0.24147 (18)	0.0492 (9)
H6	0.1222	1.1245	0.2859	0.059*
C7	0.3272 (6)	0.7039 (5)	0.30781 (16)	0.0396 (7)
C8	0.4613 (6)	0.5332 (5)	0.35262 (17)	0.0442 (8)
H8A	0.5407	0.4215	0.3228	0.053*
H8B	0.6147	0.5938	0.3739	0.053*
C9	0.2546 (7)	0.4374 (5)	0.40990 (17)	0.0468 (8)
H9A	0.1956	0.5453	0.4433	0.056*
H9B	0.0886	0.3960	0.3891	0.056*
C10	0.3694 (6)	0.2483 (5)	0.44866 (17)	0.0437 (8)
C11	0.8049 (7)	0.8513 (6)	0.12881 (19)	0.0561 (10)
H11A	0.9893	0.9016	0.1341	0.067*
H11B	0.7911	0.8271	0.0801	0.067*
H11C	0.7743	0.7208	0.1562	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0936 (8)	0.0975 (9)	0.0604 (6)	0.0060 (7)	0.0040 (6)	0.0424 (6)
O1	0.0262 (11)	0.0745 (17)	0.0765 (17)	0.0014 (11)	−0.0078 (11)	0.0376 (14)
O2	0.0694 (18)	0.087 (2)	0.090 (2)	0.0396 (16)	0.0279 (16)	0.0509 (17)
O3	0.095 (2)	0.081 (2)	0.0711 (19)	0.0421 (17)	0.0320 (16)	0.0445 (16)
N1	0.0246 (12)	0.0503 (16)	0.0477 (15)	0.0015 (12)	−0.0063 (12)	0.0195 (13)
C1	0.0326 (16)	0.0368 (17)	0.0493 (19)	−0.0006 (13)	−0.0128 (14)	0.0105 (14)
C2	0.0360 (16)	0.0434 (18)	0.0427 (18)	−0.0029 (14)	−0.0102 (14)	0.0102 (14)
C3	0.051 (2)	0.052 (2)	0.050 (2)	−0.0023 (17)	−0.0102 (16)	0.0185 (17)
C4	0.066 (2)	0.048 (2)	0.069 (3)	0.0076 (19)	−0.019 (2)	0.0244 (19)
C5	0.065 (2)	0.042 (2)	0.075 (3)	0.0200 (18)	−0.014 (2)	0.0042 (19)
C6	0.0474 (19)	0.0468 (19)	0.052 (2)	0.0069 (16)	−0.0061 (16)	0.0051 (16)
C7	0.0284 (16)	0.0479 (19)	0.0415 (17)	0.0030 (13)	−0.0059 (13)	0.0110 (14)
C8	0.0305 (16)	0.0520 (19)	0.0481 (19)	0.0028 (14)	−0.0067 (14)	0.0200 (16)
C9	0.0398 (17)	0.050 (2)	0.0474 (19)	0.0075 (15)	0.0019 (15)	0.0169 (16)
C10	0.0350 (17)	0.0481 (19)	0.0450 (18)	0.0026 (14)	0.0019 (14)	0.0148 (15)
C11	0.050 (2)	0.063 (2)	0.052 (2)	0.0112 (18)	0.0030 (17)	0.0125 (18)

Cl1—C3	1.741 (4)	C4—H4	0.9300
O1—C7	1.222 (3)	C5—C6	1.383 (5)
O2—C10	1.210 (4)	C5—H5	0.9300
O3—C10	1.279 (4)	C6—H6	0.9300
O3—H3O	0.831 (19)	C7—C8	1.512 (4)
N1—C7	1.338 (4)	C8—C9	1.510 (4)
N1—C1	1.427 (4)	C8—H8A	0.9700
N1—H1N	0.834 (18)	C8—H8B	0.9700
C1—C6	1.387 (4)	C9—C10	1.493 (4)
C1—C2	1.397 (4)	C9—H9A	0.9700
C2—C3	1.394 (4)	C9—H9B	0.9700
C2—C11	1.503 (4)	C11—H11A	0.9600
C3—C4	1.376 (5)	C11—H11B	0.9600
C4—C5	1.374 (5)	C11—H11C	0.9600
C10—O3—H3O	112 (3)	O1—C7—C8	121.8 (3)
C7—N1—C1	125.5 (2)	N1—C7—C8	114.8 (2)
C7—N1—H1N	119 (2)	C9—C8—C7	112.7 (2)
C1—N1—H1N	115 (2)	C9—C8—H8A	109.0
C6—C1—C2	121.4 (3)	C7—C8—H8A	109.0
C6—C1—N1	119.7 (3)	C9—C8—H8B	109.0
C2—C1—N1	118.8 (3)	C7—C8—H8B	109.0
C3—C2—C1	116.3 (3)	H8A—C8—H8B	107.8
C3—C2—C11	121.9 (3)	C10—C9—C8	114.1 (3)
C1—C2—C11	121.7 (3)	C10—C9—H9A	108.7
C4—C3—C2	122.9 (3)	C8—C9—H9A	108.7
C4—C3—Cl1	117.6 (3)	C10—C9—H9B	108.7
C2—C3—Cl1	119.5 (3)	C8—C9—H9B	108.7
C5—C4—C3	119.3 (3)	H9A—C9—H9B	107.6
C5—C4—H4	120.3	O2—C10—O3	122.5 (3)
C3—C4—H4	120.3	O2—C10—C9	122.8 (3)
C4—C5—C6	120.0 (3)	O3—C10—C9	114.7 (3)
C4—C5—H5	120.0	C2—C11—H11A	109.5
C6—C5—H5	120.0	C2—C11—H11B	109.5
C5—C6—C1	120.0 (3)	H11A—C11—H11B	109.5
C5—C6—H6	120.0	C2—C11—H11C	109.5
C1—C6—H6	120.0	H11A—C11—H11C	109.5
O1—C7—N1	123.3 (3)	H11B—C11—H11C	109.5
C7—N1—C1—C6	45.2 (5)	C3—C4—C5—C6	1.0 (6)
C7—N1—C1—C2	−135.5 (3)	C4—C5—C6—C1	−0.9 (6)
C6—C1—C2—C3	2.8 (5)	C2—C1—C6—C5	−1.1 (5)
N1—C1—C2—C3	−176.5 (3)	N1—C1—C6—C5	178.2 (3)
C6—C1—C2—C11	−175.6 (3)	C1—N1—C7—O1	1.3 (6)
N1—C1—C2—C11	5.1 (5)	C1—N1—C7—C8	178.8 (3)
C1—C2—C3—C4	−2.7 (5)	O1—C7—C8—C9	−17.7 (5)
C11—C2—C3—C4	175.7 (4)	N1—C7—C8—C9	164.6 (3)
C1—C2—C3—Cl1	177.4 (2)	C7—C8—C9—C10	171.9 (3)
C11—C2—C3—Cl1	−4.2 (5)	C8—C9—C10—O2	−16.0 (5)
C2—C3—C4—C5	0.8 (6)	C8—C9—C10—O3	165.6 (3)
Cl1—C3—C4—C5	−179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.83 (2)	1.84 (2)	2.666 (3)	176 (5)
N1—H1N···O1ii	0.83 (2)	2.10 (2)	2.905 (3)	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)	1.84 (2)	2.666 (3)	176 (5)
N1—H1N⋯O1ii	0.83 (2)	2.10 (2)	2.905 (3)	163 (3)

Symmetry codes: (i) ; (ii) .