N-(3-Chloro-4-methyl-phen-yl)succinamic acid.

In the crystal structure of the title compound, C(11)H(12)ClNO(3), the asymmetric unit contains two independent mol-ecules. The N-H bond in the amide segment is anti to the meta-Cl atom in the benzene ring, in both molecules. The amide and carboxyl C=O bonds are also anti to each other and anti to the H atoms on the adjacent -CH(2) groups. Furthermore, the C=O and O-H bonds of the acid group are in syn positions with respect to each other. The dihedral angles between the benzene ring and the amide group are 40.6 (2) and 44.9 (3)° in the two independent molecules. In the crystal, mol-ecules are packed into sheets parallel to the (11-3) plane through O-H⋯O and 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 ▶). For N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶). For N-chloro­aryl­amides, see: Gowda et al. (2003 ▶); Jyothi & Gowda (2004 ▶). For N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C11H12ClNO3

M = 241.67

Triclinic,

a = 6.8788 (9) Å

b = 7.9713 (9) Å

c = 21.119 (3) Å

α = 86.76 (1)°

β = 86.48 (1)°

γ = 79.45 (1)°

V = 1135.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.42 × 0.14 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.875, T max = 0.974

6890 measured reflections

4066 independent reflections

2649 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.159

S = 1.26

4066 reflections

303 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.29 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/S1600536812007623/bt5820sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007623/bt5820Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007623/bt5820Isup3.cml

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

C11H12ClNO3	Z = 4
Mr = 241.67	F(000) = 504
Triclinic, P1	Dx = 1.414 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8788 (9) Å	Cell parameters from 1965 reflections
b = 7.9713 (9) Å	θ = 2.6–27.8°
c = 21.119 (3) Å	µ = 0.33 mm−1
α = 86.76 (1)°	T = 293 K
β = 86.48 (1)°	Needle, colourless
γ = 79.45 (1)°	0.42 × 0.14 × 0.08 mm
V = 1135.1 (3) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4066 independent reflections
Radiation source: fine-focus sealed tube	2649 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Rotation method data acquisition using ω and phi scans	θmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −8→7
Tmin = 0.875, Tmax = 0.974	k = −9→5
6890 measured reflections	l = −25→24

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ2(Fo2) + (0.0164P)2 + 2.1147P] where P = (Fo2 + 2Fc2)/3
4066 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.23 e Å−3
4 restraints	Δρmin = −0.29 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	0.9701 (7)	0.4350 (5)	0.2737 (2)	0.0373 (11)
C2	0.8270 (7)	0.4875 (6)	0.3209 (2)	0.0395 (11)
H2	0.6996	0.4647	0.3192	0.047*
C3	0.8765 (7)	0.5746 (6)	0.3707 (2)	0.0406 (11)
C4	1.0621 (8)	0.6124 (6)	0.3758 (2)	0.0462 (12)
C5	1.2006 (7)	0.5579 (6)	0.3278 (2)	0.0508 (13)
H5	1.3280	0.5803	0.3297	0.061*
C6	1.1575 (7)	0.4713 (6)	0.2771 (2)	0.0492 (13)
H6	1.2545	0.4376	0.2454	0.059*
C7	0.7569 (7)	0.3702 (6)	0.1926 (2)	0.0442 (12)
C8	0.7444 (8)	0.2452 (6)	0.1422 (2)	0.0520 (14)
H8A	0.8542	0.2459	0.1111	0.062*
H8B	0.7571	0.1310	0.1618	0.062*
C9	0.5540 (8)	0.2863 (7)	0.1088 (3)	0.0643 (16)
H9A	0.4443	0.2925	0.1402	0.077*
H9B	0.5453	0.3979	0.0872	0.077*
C10	0.5339 (9)	0.1589 (7)	0.0616 (3)	0.0625 (16)
C11	1.1143 (8)	0.7015 (7)	0.4315 (2)	0.0641 (16)
H11A	1.0990	0.6329	0.4698	0.077*
H11B	1.0282	0.8103	0.4347	0.077*
H11C	1.2491	0.7180	0.4258	0.077*
N1	0.9276 (6)	0.3407 (5)	0.22252 (18)	0.0444 (10)
H1N	1.019 (5)	0.261 (4)	0.210 (2)	0.053*
O1	0.6196 (5)	0.4867 (4)	0.20492 (16)	0.0577 (10)
O2	0.6511 (6)	0.0290 (5)	0.0539 (2)	0.0819 (14)
O3	0.3768 (7)	0.2020 (6)	0.0292 (2)	0.1039 (18)
H3O	0.370 (11)	0.124 (6)	0.006 (3)	0.125*
Cl1	0.6908 (2)	0.63733 (18)	0.42917 (6)	0.0627 (4)
C12	0.5122 (7)	1.0684 (5)	0.7315 (2)	0.0391 (11)
C13	0.6607 (7)	0.9993 (6)	0.6890 (2)	0.0422 (12)
H13	0.7919	1.0053	0.6953	0.051*
C14	0.6131 (7)	0.9208 (5)	0.6365 (2)	0.0397 (11)
C15	0.4223 (7)	0.9079 (6)	0.6246 (2)	0.0415 (11)
C16	0.2766 (7)	0.9777 (7)	0.6688 (2)	0.0534 (14)
H16	0.1457	0.9702	0.6628	0.064*
C17	0.3185 (7)	1.0581 (6)	0.7213 (2)	0.0473 (12)
H17	0.2168	1.1048	0.7497	0.057*
C18	0.7041 (8)	1.1042 (7)	0.8223 (2)	0.0573 (15)
C19	0.7225 (8)	1.2230 (7)	0.8742 (3)	0.0707 (18)
H19A	0.6436	1.3344	0.8645	0.085*
H19B	0.6696	1.1790	0.9141	0.085*
C20	0.9289 (9)	1.2424 (8)	0.8816 (3)	0.0722 (18)
H20A	0.9796	1.2907	0.8422	0.087*
H20B	1.0086	1.1303	0.8893	0.087*
C21	0.9521 (10)	1.3530 (7)	0.9343 (3)	0.0619 (16)
C22	0.3714 (8)	0.8265 (7)	0.5666 (2)	0.0644 (16)
H22A	0.4427	0.7112	0.5655	0.077*
H22B	0.4072	0.8903	0.5292	0.077*
H22C	0.2317	0.8261	0.5682	0.077*
N2	0.5543 (6)	1.1566 (5)	0.78445 (19)	0.0485 (11)
H2N	0.485 (6)	1.254 (4)	0.790 (2)	0.058*
O4	0.8183 (7)	0.9688 (5)	0.8168 (2)	0.0951 (17)
O5	0.8321 (7)	1.3876 (6)	0.9774 (2)	0.0946 (16)
O6	1.1205 (9)	1.4050 (7)	0.9300 (2)	0.1004 (16)
H6O	1.122 (11)	1.457 (8)	0.963 (2)	0.121*
Cl2	0.8053 (2)	0.84014 (18)	0.58273 (6)	0.0599 (4)

	U11	U22	U33	U12	U13	U23
C1	0.038 (3)	0.036 (3)	0.037 (2)	0.001 (2)	−0.008 (2)	−0.010 (2)
C2	0.038 (3)	0.042 (3)	0.040 (3)	−0.007 (2)	−0.007 (2)	−0.009 (2)
C3	0.044 (3)	0.038 (3)	0.038 (3)	0.001 (2)	−0.005 (2)	−0.011 (2)
C4	0.056 (3)	0.040 (3)	0.045 (3)	−0.009 (2)	−0.013 (2)	−0.006 (2)
C5	0.040 (3)	0.056 (3)	0.059 (3)	−0.012 (2)	−0.009 (2)	−0.012 (3)
C6	0.046 (3)	0.056 (3)	0.044 (3)	0.000 (2)	−0.001 (2)	−0.015 (2)
C7	0.051 (3)	0.040 (3)	0.040 (3)	−0.001 (2)	−0.006 (2)	−0.014 (2)
C8	0.068 (4)	0.038 (3)	0.048 (3)	0.004 (2)	−0.020 (3)	−0.019 (2)
C9	0.057 (4)	0.069 (4)	0.068 (4)	0.001 (3)	−0.020 (3)	−0.037 (3)
C10	0.063 (4)	0.064 (4)	0.063 (4)	−0.002 (3)	−0.020 (3)	−0.032 (3)
C11	0.068 (4)	0.072 (4)	0.059 (3)	−0.017 (3)	−0.017 (3)	−0.025 (3)
N1	0.044 (3)	0.042 (2)	0.046 (2)	0.0057 (19)	−0.0109 (19)	−0.0200 (19)
O1	0.053 (2)	0.055 (2)	0.061 (2)	0.0148 (18)	−0.0208 (17)	−0.0312 (18)
O2	0.081 (3)	0.067 (3)	0.097 (3)	0.016 (2)	−0.042 (2)	−0.051 (2)
O3	0.088 (3)	0.095 (3)	0.126 (4)	0.029 (3)	−0.065 (3)	−0.073 (3)
Cl1	0.0659 (9)	0.0708 (9)	0.0511 (8)	−0.0068 (7)	0.0061 (6)	−0.0275 (7)
C12	0.047 (3)	0.030 (2)	0.041 (3)	−0.002 (2)	−0.009 (2)	−0.010 (2)
C13	0.030 (3)	0.049 (3)	0.048 (3)	−0.002 (2)	−0.006 (2)	−0.014 (2)
C14	0.041 (3)	0.034 (3)	0.043 (3)	−0.001 (2)	−0.003 (2)	−0.007 (2)
C15	0.041 (3)	0.044 (3)	0.042 (3)	−0.012 (2)	−0.004 (2)	−0.005 (2)
C16	0.034 (3)	0.072 (4)	0.057 (3)	−0.014 (3)	−0.008 (2)	−0.010 (3)
C17	0.038 (3)	0.055 (3)	0.048 (3)	−0.003 (2)	−0.001 (2)	−0.011 (2)
C18	0.059 (4)	0.055 (3)	0.057 (3)	0.006 (3)	−0.017 (3)	−0.028 (3)
C19	0.068 (4)	0.072 (4)	0.070 (4)	0.010 (3)	−0.024 (3)	−0.045 (3)
C20	0.082 (5)	0.066 (4)	0.071 (4)	−0.006 (3)	−0.019 (3)	−0.040 (3)
C21	0.073 (4)	0.061 (4)	0.055 (4)	−0.011 (3)	−0.021 (3)	−0.019 (3)
C22	0.066 (4)	0.082 (4)	0.054 (3)	−0.029 (3)	−0.010 (3)	−0.017 (3)
N2	0.049 (3)	0.041 (2)	0.053 (2)	0.0089 (19)	−0.011 (2)	−0.024 (2)
O4	0.105 (3)	0.072 (3)	0.097 (3)	0.048 (3)	−0.062 (3)	−0.058 (2)
O5	0.109 (4)	0.111 (4)	0.077 (3)	−0.045 (3)	0.005 (3)	−0.053 (3)
O6	0.121 (4)	0.126 (4)	0.071 (3)	−0.053 (3)	−0.001 (3)	−0.049 (3)
Cl2	0.0528 (8)	0.0685 (9)	0.0563 (8)	0.0000 (7)	0.0034 (6)	−0.0261 (7)

C1—C6	1.378 (6)	C12—C13	1.375 (6)
C1—C2	1.384 (6)	C12—C17	1.380 (6)
C1—N1	1.424 (5)	C12—N2	1.426 (5)
C2—C3	1.385 (6)	C13—C14	1.387 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.376 (7)	C14—C15	1.375 (6)
C3—Cl1	1.746 (4)	C14—Cl2	1.743 (4)
C4—C5	1.380 (7)	C15—C16	1.387 (6)
C4—C11	1.502 (6)	C15—C22	1.507 (6)
C5—C6	1.382 (6)	C16—C17	1.383 (6)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—O1	1.223 (5)	C18—O4	1.220 (6)
C7—N1	1.344 (6)	C18—N2	1.334 (6)
C7—C8	1.516 (6)	C18—C19	1.515 (6)
C8—C9	1.499 (7)	C19—C20	1.475 (8)
C8—H8A	0.9700	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C10	1.492 (6)	C20—C21	1.491 (7)
C9—H9A	0.9700	C20—H20A	0.9700
C9—H9B	0.9700	C20—H20B	0.9700
C10—O2	1.202 (6)	C21—O5	1.200 (7)
C10—O3	1.297 (6)	C21—O6	1.297 (7)
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
N1—H1N	0.853 (19)	N2—H2N	0.843 (19)
O3—H3O	0.83 (2)	O6—H6O	0.83 (2)
C6—C1—C2	119.4 (4)	C13—C12—C17	119.5 (4)
C6—C1—N1	119.7 (4)	C13—C12—N2	121.0 (4)
C2—C1—N1	120.9 (4)	C17—C12—N2	119.5 (4)
C1—C2—C3	118.9 (4)	C12—C13—C14	119.4 (4)
C1—C2—H2	120.5	C12—C13—H13	120.3
C3—C2—H2	120.5	C14—C13—H13	120.3
C4—C3—C2	123.3 (4)	C15—C14—C13	123.0 (4)
C4—C3—Cl1	119.6 (3)	C15—C14—Cl2	119.1 (3)
C2—C3—Cl1	117.1 (4)	C13—C14—Cl2	117.8 (4)
C3—C4—C5	116.0 (4)	C14—C15—C16	116.0 (4)
C3—C4—C11	122.3 (5)	C14—C15—C22	122.7 (4)
C5—C4—C11	121.6 (5)	C16—C15—C22	121.3 (5)
C4—C5—C6	122.7 (5)	C17—C16—C15	122.5 (5)
C4—C5—H5	118.7	C17—C16—H16	118.7
C6—C5—H5	118.7	C15—C16—H16	118.7
C1—C6—C5	119.7 (4)	C12—C17—C16	119.6 (4)
C1—C6—H6	120.1	C12—C17—H17	120.2
C5—C6—H6	120.1	C16—C17—H17	120.2
O1—C7—N1	123.6 (4)	O4—C18—N2	123.1 (4)
O1—C7—C8	121.7 (4)	O4—C18—C19	121.3 (5)
N1—C7—C8	114.7 (4)	N2—C18—C19	115.6 (4)
C9—C8—C7	112.8 (4)	C20—C19—C18	112.7 (5)
C9—C8—H8A	109.0	C20—C19—H19A	109.1
C7—C8—H8A	109.0	C18—C19—H19A	109.1
C9—C8—H8B	109.0	C20—C19—H19B	109.1
C7—C8—H8B	109.0	C18—C19—H19B	109.1
H8A—C8—H8B	107.8	H19A—C19—H19B	107.8
C10—C9—C8	113.5 (4)	C19—C20—C21	113.7 (5)
C10—C9—H9A	108.9	C19—C20—H20A	108.8
C8—C9—H9A	108.9	C21—C20—H20A	108.8
C10—C9—H9B	108.9	C19—C20—H20B	108.8
C8—C9—H9B	108.9	C21—C20—H20B	108.8
H9A—C9—H9B	107.7	H20A—C20—H20B	107.7
O2—C10—O3	122.9 (5)	O5—C21—O6	122.6 (5)
O2—C10—C9	123.8 (5)	O5—C21—C20	124.6 (6)
O3—C10—C9	113.3 (5)	O6—C21—C20	112.8 (6)
C4—C11—H11A	109.5	C15—C22—H22A	109.5
C4—C11—H11B	109.5	C15—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C4—C11—H11C	109.5	C15—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5
C7—N1—C1	125.1 (4)	C18—N2—C12	125.3 (4)
C7—N1—H1N	118 (3)	C18—N2—H2N	118 (4)
C1—N1—H1N	117 (3)	C12—N2—H2N	116 (3)
C10—O3—H3O	109 (5)	C21—O6—H6O	105 (5)
C6—C1—C2—C3	−0.4 (7)	C17—C12—C13—C14	0.1 (7)
N1—C1—C2—C3	178.1 (4)	N2—C12—C13—C14	−177.3 (4)
C1—C2—C3—C4	0.1 (7)	C12—C13—C14—C15	0.0 (7)
C1—C2—C3—Cl1	−179.8 (3)	C12—C13—C14—Cl2	178.3 (4)
C2—C3—C4—C5	−0.1 (7)	C13—C14—C15—C16	−0.5 (7)
Cl1—C3—C4—C5	179.8 (4)	Cl2—C14—C15—C16	−178.8 (4)
C2—C3—C4—C11	−177.7 (5)	C13—C14—C15—C22	178.3 (5)
Cl1—C3—C4—C11	2.1 (7)	Cl2—C14—C15—C22	0.0 (7)
C3—C4—C5—C6	0.4 (8)	C14—C15—C16—C17	1.0 (8)
C11—C4—C5—C6	178.0 (5)	C22—C15—C16—C17	−177.8 (5)
C2—C1—C6—C5	0.6 (7)	C13—C12—C17—C16	0.3 (7)
N1—C1—C6—C5	−177.9 (4)	N2—C12—C17—C16	177.8 (5)
C4—C5—C6—C1	−0.6 (8)	C15—C16—C17—C12	−0.9 (8)
O1—C7—C8—C9	2.6 (8)	O4—C18—C19—C20	44.0 (9)
N1—C7—C8—C9	−178.3 (5)	N2—C18—C19—C20	−137.0 (6)
C7—C8—C9—C10	−176.6 (5)	C18—C19—C20—C21	−177.5 (5)
C8—C9—C10—O2	5.2 (9)	C19—C20—C21—O5	19.0 (9)
C8—C9—C10—O3	−174.7 (6)	C19—C20—C21—O6	−163.0 (6)
O1—C7—N1—C1	2.5 (8)	O4—C18—N2—C12	−3.1 (10)
C8—C7—N1—C1	−176.6 (4)	C19—C18—N2—C12	178.0 (5)
C6—C1—N1—C7	−141.8 (5)	C13—C12—N2—C18	−44.3 (8)
C2—C1—N1—C7	39.7 (7)	C17—C12—N2—C18	138.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.85 (2)	2.05 (2)	2.882 (5)	165 (5)
O3—H3O···O2ii	0.83 (2)	1.83 (2)	2.654 (5)	173 (7)
N2—H2N···O1iii	0.84 (2)	2.07 (2)	2.891 (5)	165 (5)
O6—H6O···O5iv	0.83 (2)	1.90 (3)	2.703 (5)	164 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.85 (2)	2.05 (2)	2.882 (5)	165 (5)
O3—H3O⋯O2ii	0.83 (2)	1.83 (2)	2.654 (5)	173 (7)
N2—H2N⋯O1iii	0.84 (2)	2.07 (2)	2.891 (5)	165 (5)
O6—H6O⋯O5iv	0.83 (2)	1.90 (3)	2.703 (5)	164 (7)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .