N-(2-Chloro-4-methyl-phen-yl)succinamic acid.

In the title compound, C(11)H(12)ClNO(3), the N-C=O fragment is twisted from the plane of the attached benzene ring by 48.39 (12)°. The carb-oxy-lic acid group is involved in O-H⋯O hydrogen bonding, which links pairs of mol-ecules into centrosymmetric dimers. N-H⋯O hydrogen bonds link these dimers, related by translation along the a axis, into ribbons.

Related literature

For the crystal structures of related compounds studied by our group, see: Gowda et al. (2012 ▶) and references therein.

Experimental

Crystal data

C11H12ClNO3

M = 241.67

Triclinic,

a = 4.8097 (8) Å

b = 7.3909 (9) Å

c = 16.147 (2) Å

α = 85.15 (1)°

β = 85.86 (1)°

γ = 89.57 (1)°

V = 570.45 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.40 × 0.18 × 0.09 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.881, T max = 0.971

3625 measured reflections

2284 independent reflections

1883 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.120

S = 1.11

2284 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 RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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/S1600536812005648/cv5244sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005648/cv5244Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005648/cv5244Isup3.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 = 4.8097 (8) Å	Cell parameters from 2016 reflections
b = 7.3909 (9) Å	θ = 2.5–27.9°
c = 16.147 (2) Å	µ = 0.33 mm−1
α = 85.15 (1)°	T = 293 K
β = 85.86 (1)°	Rod, colourless
γ = 89.57 (1)°	0.40 × 0.18 × 0.09 mm
V = 570.45 (14) Å3

Oxford Xcalibur diffractometer with Sapphire CCD detector	2284 independent reflections
Radiation source: fine-focus sealed tube	1883 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→5
Tmin = 0.881, Tmax = 0.971	k = −9→9
3625 measured reflections	l = −17→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0348P)2 + 0.5262P] where P = (Fo2 + 2Fc2)/3
2284 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.25 e Å−3

Experimental. 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
C1	0.7464 (5)	0.1423 (3)	0.72556 (16)	0.0372 (5)
C2	0.6617 (5)	0.1119 (3)	0.64792 (16)	0.0397 (6)
C3	0.7600 (6)	−0.0346 (3)	0.60606 (18)	0.0479 (6)
H3	0.6972	−0.0528	0.5543	0.057*
C4	0.9510 (6)	−0.1542 (4)	0.64083 (19)	0.0516 (7)
C5	1.0408 (6)	−0.1206 (4)	0.7175 (2)	0.0544 (7)
H5	1.1728	−0.1976	0.7412	0.065*
C6	0.9412 (5)	0.0232 (4)	0.76017 (18)	0.0465 (6)
H6	1.0040	0.0408	0.8120	0.056*
C7	0.7910 (5)	0.4059 (3)	0.80500 (15)	0.0386 (6)
C8	0.6293 (5)	0.5544 (4)	0.84608 (17)	0.0431 (6)
H8A	0.4480	0.5081	0.8679	0.052*
H8B	0.5999	0.6544	0.8047	0.052*
C9	0.7800 (5)	0.6234 (4)	0.91616 (17)	0.0449 (6)
H9A	0.7896	0.5262	0.9602	0.054*
H9B	0.9696	0.6544	0.8955	0.054*
C10	0.6475 (5)	0.7848 (4)	0.95222 (16)	0.0441 (6)
C11	1.0540 (8)	−0.3163 (4)	0.5961 (2)	0.0790 (11)
H11A	1.0422	−0.2903	0.5371	0.095*
H11B	0.9409	−0.4201	0.6151	0.095*
H11C	1.2442	−0.3414	0.6075	0.095*
N1	0.6355 (4)	0.2886 (3)	0.76914 (14)	0.0404 (5)
H1N	0.463 (4)	0.306 (4)	0.7706 (17)	0.049*
O1	1.0450 (3)	0.3984 (3)	0.80286 (14)	0.0594 (6)
O2	0.4442 (4)	0.8624 (3)	0.92593 (15)	0.0741 (7)
O3	0.7748 (6)	0.8378 (4)	1.01368 (17)	0.0888 (9)
H3O	0.696 (8)	0.924 (4)	1.035 (2)	0.107*
Cl1	0.42759 (15)	0.26087 (10)	0.60111 (5)	0.0573 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0262 (11)	0.0349 (12)	0.0506 (14)	0.0017 (9)	0.0016 (10)	−0.0079 (10)
C2	0.0289 (12)	0.0395 (13)	0.0520 (15)	0.0062 (10)	−0.0033 (10)	−0.0110 (11)
C3	0.0484 (15)	0.0411 (14)	0.0554 (16)	0.0046 (12)	0.0006 (12)	−0.0164 (12)
C4	0.0498 (16)	0.0356 (13)	0.0685 (19)	0.0076 (11)	0.0104 (14)	−0.0118 (12)
C5	0.0447 (15)	0.0441 (15)	0.073 (2)	0.0164 (12)	−0.0009 (14)	0.0012 (14)
C6	0.0374 (14)	0.0482 (15)	0.0540 (16)	0.0057 (11)	−0.0033 (11)	−0.0056 (12)
C7	0.0255 (12)	0.0447 (13)	0.0474 (14)	0.0032 (10)	−0.0044 (10)	−0.0137 (11)
C8	0.0266 (12)	0.0492 (14)	0.0570 (16)	0.0044 (10)	−0.0076 (11)	−0.0217 (12)
C9	0.0332 (13)	0.0532 (15)	0.0516 (15)	0.0059 (11)	−0.0090 (11)	−0.0192 (12)
C10	0.0353 (13)	0.0533 (15)	0.0463 (14)	−0.0003 (11)	−0.0036 (11)	−0.0192 (12)
C11	0.094 (3)	0.0468 (17)	0.095 (3)	0.0276 (17)	0.015 (2)	−0.0168 (17)
N1	0.0214 (9)	0.0463 (12)	0.0568 (13)	0.0056 (8)	−0.0042 (9)	−0.0223 (10)
O1	0.0219 (9)	0.0689 (13)	0.0934 (16)	0.0049 (8)	−0.0080 (9)	−0.0395 (12)
O2	0.0578 (13)	0.0868 (16)	0.0892 (16)	0.0282 (12)	−0.0307 (12)	−0.0551 (13)
O3	0.0870 (18)	0.0996 (19)	0.0954 (19)	0.0402 (14)	−0.0513 (15)	−0.0655 (16)
Cl1	0.0547 (4)	0.0582 (4)	0.0627 (5)	0.0234 (3)	−0.0177 (3)	−0.0183 (3)

C1—C2	1.382 (3)	C7—C8	1.512 (3)
C1—C6	1.395 (3)	C8—C9	1.512 (3)
C1—N1	1.420 (3)	C8—H8A	0.9700
C2—C3	1.387 (3)	C8—H8B	0.9700
C2—Cl1	1.736 (2)	C9—C10	1.490 (3)
C3—C4	1.385 (4)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.383 (4)	C10—O2	1.215 (3)
C4—C11	1.513 (4)	C10—O3	1.292 (3)
C5—C6	1.379 (4)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—H6	0.9300	C11—H11C	0.9600
C7—O1	1.221 (3)	N1—H1N	0.839 (17)
C7—N1	1.343 (3)	O3—H3O	0.827 (19)
C2—C1—C6	117.9 (2)	C9—C8—H8A	109.2
C2—C1—N1	121.0 (2)	C7—C8—H8B	109.2
C6—C1—N1	121.1 (2)	C9—C8—H8B	109.2
C1—C2—C3	121.6 (2)	H8A—C8—H8B	107.9
C1—C2—Cl1	119.42 (18)	C10—C9—C8	114.3 (2)
C3—C2—Cl1	118.9 (2)	C10—C9—H9A	108.7
C4—C3—C2	120.5 (3)	C8—C9—H9A	108.7
C4—C3—H3	119.8	C10—C9—H9B	108.7
C2—C3—H3	119.8	C8—C9—H9B	108.7
C5—C4—C3	117.7 (2)	H9A—C9—H9B	107.6
C5—C4—C11	121.7 (3)	O2—C10—O3	122.8 (2)
C3—C4—C11	120.6 (3)	O2—C10—C9	124.0 (2)
C6—C5—C4	122.2 (3)	O3—C10—C9	113.2 (2)
C6—C5—H5	118.9	C4—C11—H11A	109.5
C4—C5—H5	118.9	C4—C11—H11B	109.5
C5—C6—C1	120.0 (3)	H11A—C11—H11B	109.5
C5—C6—H6	120.0	C4—C11—H11C	109.5
C1—C6—H6	120.0	H11A—C11—H11C	109.5
O1—C7—N1	123.2 (2)	H11B—C11—H11C	109.5
O1—C7—C8	121.7 (2)	C7—N1—C1	124.10 (19)
N1—C7—C8	115.08 (19)	C7—N1—H1N	117.9 (19)
C7—C8—C9	111.9 (2)	C1—N1—H1N	117.9 (19)
C7—C8—H8A	109.2	C10—O3—H3O	113 (3)
C6—C1—C2—C3	1.7 (4)	C2—C1—C6—C5	−0.8 (4)
N1—C1—C2—C3	−177.4 (2)	N1—C1—C6—C5	178.4 (2)
C6—C1—C2—Cl1	−178.02 (19)	O1—C7—C8—C9	−28.9 (4)
N1—C1—C2—Cl1	2.8 (3)	N1—C7—C8—C9	153.3 (2)
C1—C2—C3—C4	−1.0 (4)	C7—C8—C9—C10	173.0 (2)
Cl1—C2—C3—C4	178.8 (2)	C8—C9—C10—O2	−3.6 (4)
C2—C3—C4—C5	−0.7 (4)	C8—C9—C10—O3	177.9 (3)
C2—C3—C4—C11	178.7 (3)	O1—C7—N1—C1	0.6 (4)
C3—C4—C5—C6	1.7 (4)	C8—C7—N1—C1	178.4 (2)
C11—C4—C5—C6	−177.8 (3)	C2—C1—N1—C7	−132.0 (3)
C4—C5—C6—C1	−1.0 (4)	C6—C1—N1—C7	48.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.16 (2)	2.973 (3)	163 (3)
O3—H3O···O2ii	0.83 (2)	1.85 (2)	2.674 (3)	172 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.16 (2)	2.973 (3)	163 (3)
O3—H3O⋯O2ii	0.83 (2)	1.85 (2)	2.674 (3)	172 (4)

Symmetry codes: (i) ; (ii) .