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

The title compound, C(11)H(12)ClNO(3), crystallizes with two independent mol-ecules in the asymmetric unit in which the dihedral angles between the benzene ring and the amide group are 55.0 (2) and 28.2 (3)°. The two independent mol-ecules are linked by an N-H⋯O hydrogen bond. In the crystal, mol-ecules form inversion dimers via pairs of O-H⋯O hydrogen bonds. These dimers are linked into sheets parallel to (11-3) 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 of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶).

Experimental

Crystal data

C11H12ClNO3

M = 241.67

Triclinic,

a = 6.6253 (8) Å

b = 7.9634 (9) Å

c = 21.545 (3) Å

α = 88.57 (1)°

β = 81.99 (1)°

γ = 84.25 (1)°

V = 1119.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.48 × 0.16 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.857, T max = 0.990

6984 measured reflections

3864 independent reflections

2640 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.090

wR(F 2) = 0.155

S = 1.33

3864 reflections

303 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis 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/S1600536812024567/bt5936sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024567/bt5936Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024567/bt5936Isup3.cml

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

C11H12ClNO3	Z = 4
Mr = 241.67	F(000) = 504
Triclinic, P1	Dx = 1.433 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6253 (8) Å	Cell parameters from 1701 reflections
b = 7.9634 (9) Å	θ = 2.6–27.4°
c = 21.545 (3) Å	µ = 0.33 mm−1
α = 88.57 (1)°	T = 293 K
β = 81.99 (1)°	Plate, colourless
γ = 84.25 (1)°	0.48 × 0.16 × 0.03 mm
V = 1119.9 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3864 independent reflections
Radiation source: fine-focus sealed tube	2640 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Rotation method data acquisition using ω and phi scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.857, Tmax = 0.990	k = −9→8
6984 measured reflections	l = −23→25

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)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.33	w = 1/[σ2(Fo2) + (0.0064P)2 + 2.5267P] where P = (Fo2 + 2Fc2)/3
3864 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.35 e Å−3
4 restraints	Δρmin = −0.29 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	1.1028 (3)	0.7244 (2)	0.43623 (7)	0.0669 (5)
O1	0.6519 (6)	0.5020 (5)	0.19988 (18)	0.0599 (12)
O2	0.6714 (7)	0.0487 (6)	0.0438 (2)	0.0788 (15)
O3	0.3608 (7)	0.1779 (6)	0.0426 (2)	0.0824 (15)
H3O	0.352 (11)	0.105 (6)	0.017 (3)	0.099*
N1	0.9291 (7)	0.3357 (5)	0.2222 (2)	0.0454 (12)
H1N	1.017 (6)	0.251 (5)	0.212 (2)	0.055*
C1	0.9694 (8)	0.4313 (6)	0.2738 (2)	0.0394 (13)
C2	0.8186 (8)	0.4669 (6)	0.3242 (2)	0.0404 (13)
H2	0.6905	0.4290	0.3238	0.049*
C3	0.8529 (8)	0.5574 (6)	0.3753 (2)	0.0380 (12)
C4	1.0473 (8)	0.6116 (6)	0.3735 (2)	0.0402 (13)
C5	1.1991 (8)	0.5761 (7)	0.3242 (2)	0.0473 (14)
H5	1.3276	0.6130	0.3247	0.057*
C6	1.1619 (8)	0.4854 (7)	0.2735 (2)	0.0464 (14)
H6	1.2643	0.4614	0.2399	0.056*
C7	0.7719 (8)	0.3752 (7)	0.1897 (2)	0.0409 (13)
C8	0.7563 (9)	0.2520 (7)	0.1387 (3)	0.0535 (16)
H8A	0.8685	0.2620	0.1051	0.064*
H8B	0.7703	0.1380	0.1556	0.064*
C9	0.5581 (9)	0.2808 (7)	0.1124 (3)	0.0561 (16)
H9A	0.5458	0.3940	0.0948	0.067*
H9B	0.4461	0.2737	0.1462	0.067*
C10	0.5379 (10)	0.1570 (8)	0.0627 (3)	0.0557 (16)
C11	0.6861 (9)	0.5963 (7)	0.4295 (2)	0.0574 (16)
H11A	0.5651	0.5470	0.4223	0.069*
H11B	0.6561	0.7163	0.4333	0.069*
H11C	0.7308	0.5502	0.4675	0.069*
Cl2	0.6698 (2)	1.1376 (2)	0.44331 (7)	0.0594 (4)
O4	0.1817 (6)	1.0173 (5)	0.19059 (18)	0.0632 (12)
O5	0.1879 (7)	0.5752 (6)	0.0324 (2)	0.0846 (16)
O6	−0.1414 (8)	0.6470 (7)	0.0550 (2)	0.0920 (17)
H6O	−0.157 (11)	0.576 (7)	0.029 (3)	0.110*
N2	0.4570 (7)	0.8506 (5)	0.2130 (2)	0.0428 (11)
H2N	0.531 (7)	0.759 (4)	0.204 (2)	0.051*
C12	0.5057 (8)	0.9318 (6)	0.2666 (2)	0.0354 (12)
C13	0.3572 (8)	1.0248 (6)	0.3070 (2)	0.0414 (13)
H13	0.2243	1.0431	0.2973	0.050*
C14	0.4031 (8)	1.0913 (6)	0.3619 (2)	0.0372 (12)
C15	0.6025 (8)	1.0644 (6)	0.3742 (2)	0.0397 (13)
C16	0.7513 (8)	0.9745 (7)	0.3338 (2)	0.0477 (14)
H16	0.8849	0.9587	0.3430	0.057*
C17	0.7044 (8)	0.9074 (7)	0.2796 (2)	0.0446 (14)
H17	0.8054	0.8468	0.2524	0.054*
C18	0.3015 (8)	0.8908 (7)	0.1804 (2)	0.0433 (13)
C19	0.2833 (9)	0.7696 (7)	0.1289 (2)	0.0512 (15)
H19A	0.3750	0.7969	0.0917	0.061*
H19B	0.3266	0.6558	0.1420	0.061*
C20	0.0720 (9)	0.7745 (8)	0.1128 (3)	0.0642 (18)
H20A	0.0298	0.8884	0.0995	0.077*
H20B	−0.0193	0.7489	0.1503	0.077*
C21	0.0466 (10)	0.6560 (8)	0.0627 (3)	0.0535 (15)
C22	0.2383 (8)	1.1841 (7)	0.4074 (2)	0.0525 (15)
H22A	0.1150	1.2044	0.3885	0.063*
H22B	0.2824	1.2899	0.4177	0.063*
H22C	0.2127	1.1171	0.4448	0.063*

	U11	U22	U33	U12	U13	U23
Cl1	0.0740 (11)	0.0742 (11)	0.0584 (9)	−0.0042 (9)	−0.0273 (8)	−0.0302 (8)
O1	0.072 (3)	0.048 (2)	0.061 (3)	0.024 (2)	−0.030 (2)	−0.029 (2)
O2	0.085 (3)	0.071 (3)	0.084 (3)	0.020 (3)	−0.038 (3)	−0.052 (3)
O3	0.082 (3)	0.083 (4)	0.087 (3)	0.016 (3)	−0.041 (3)	−0.054 (3)
N1	0.050 (3)	0.042 (3)	0.043 (3)	0.016 (2)	−0.014 (2)	−0.025 (2)
C1	0.048 (3)	0.035 (3)	0.034 (3)	0.007 (3)	−0.008 (3)	−0.012 (2)
C2	0.043 (3)	0.039 (3)	0.041 (3)	−0.002 (2)	−0.011 (3)	−0.007 (2)
C3	0.044 (3)	0.038 (3)	0.030 (3)	0.008 (2)	−0.005 (2)	−0.010 (2)
C4	0.047 (3)	0.039 (3)	0.036 (3)	0.001 (3)	−0.011 (3)	−0.014 (2)
C5	0.040 (3)	0.051 (4)	0.053 (3)	−0.003 (3)	−0.016 (3)	−0.009 (3)
C6	0.044 (3)	0.051 (4)	0.043 (3)	0.004 (3)	−0.003 (3)	−0.010 (3)
C7	0.050 (3)	0.037 (3)	0.036 (3)	0.004 (3)	−0.009 (3)	−0.014 (2)
C8	0.065 (4)	0.046 (4)	0.051 (3)	0.011 (3)	−0.021 (3)	−0.024 (3)
C9	0.065 (4)	0.049 (4)	0.057 (4)	0.004 (3)	−0.019 (3)	−0.026 (3)
C10	0.072 (4)	0.051 (4)	0.048 (3)	−0.003 (3)	−0.020 (3)	−0.018 (3)
C11	0.064 (4)	0.060 (4)	0.046 (3)	0.002 (3)	0.001 (3)	−0.015 (3)
Cl2	0.0647 (10)	0.0710 (11)	0.0479 (8)	−0.0085 (8)	−0.0223 (7)	−0.0176 (7)
O4	0.077 (3)	0.053 (3)	0.062 (3)	0.029 (2)	−0.036 (2)	−0.033 (2)
O5	0.072 (3)	0.096 (4)	0.089 (3)	0.003 (3)	−0.020 (3)	−0.062 (3)
O6	0.071 (3)	0.114 (4)	0.097 (4)	0.000 (3)	−0.027 (3)	−0.070 (3)
N2	0.046 (3)	0.040 (3)	0.042 (2)	0.010 (2)	−0.012 (2)	−0.018 (2)
C12	0.040 (3)	0.030 (3)	0.036 (3)	0.001 (2)	−0.007 (2)	−0.009 (2)
C13	0.039 (3)	0.042 (3)	0.044 (3)	0.004 (2)	−0.010 (3)	−0.013 (3)
C14	0.042 (3)	0.034 (3)	0.036 (3)	−0.002 (2)	−0.007 (2)	−0.006 (2)
C15	0.051 (3)	0.039 (3)	0.031 (3)	−0.002 (3)	−0.011 (2)	−0.009 (2)
C16	0.040 (3)	0.056 (4)	0.050 (3)	0.001 (3)	−0.018 (3)	−0.008 (3)
C17	0.037 (3)	0.052 (4)	0.042 (3)	0.009 (3)	−0.002 (3)	−0.014 (3)
C18	0.050 (3)	0.040 (3)	0.040 (3)	0.007 (3)	−0.010 (3)	−0.016 (3)
C19	0.068 (4)	0.042 (3)	0.044 (3)	0.009 (3)	−0.016 (3)	−0.023 (3)
C20	0.060 (4)	0.071 (4)	0.065 (4)	0.006 (3)	−0.019 (3)	−0.043 (3)
C21	0.058 (4)	0.051 (4)	0.053 (4)	0.002 (3)	−0.017 (3)	−0.019 (3)
C22	0.055 (4)	0.058 (4)	0.042 (3)	0.011 (3)	−0.009 (3)	−0.022 (3)

Cl1—C4	1.743 (5)	Cl2—C15	1.742 (5)
O1—C7	1.226 (6)	O4—C18	1.223 (6)
O2—C10	1.207 (7)	O5—C21	1.203 (6)
O3—C10	1.300 (7)	O6—C21	1.288 (7)
O3—H3O	0.82 (2)	O6—H6O	0.82 (2)
N1—C7	1.341 (6)	N2—C18	1.336 (6)
N1—C1	1.433 (6)	N2—C12	1.427 (6)
N1—H1N	0.855 (19)	N2—H2N	0.849 (19)
C1—C2	1.383 (7)	C12—C17	1.379 (7)
C1—C6	1.385 (7)	C12—C13	1.387 (6)
C2—C3	1.388 (6)	C13—C14	1.392 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.393 (7)	C14—C15	1.378 (7)
C3—C11	1.508 (7)	C14—C22	1.507 (7)
C4—C5	1.371 (7)	C15—C16	1.376 (7)
C5—C6	1.388 (7)	C16—C17	1.382 (7)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.512 (6)	C18—C19	1.514 (6)
C8—C9	1.496 (7)	C19—C20	1.485 (7)
C8—H8A	0.9700	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C10	1.502 (7)	C20—C21	1.488 (7)
C9—H9A	0.9700	C20—H20A	0.9700
C9—H9B	0.9700	C20—H20B	0.9700
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
C10—O3—H3O	111 (5)	C21—O6—H6O	114 (5)
C7—N1—C1	124.2 (4)	C18—N2—C12	128.7 (4)
C7—N1—H1N	121 (4)	C18—N2—H2N	117 (4)
C1—N1—H1N	115 (4)	C12—N2—H2N	114 (4)
C2—C1—C6	120.1 (5)	C17—C12—C13	120.0 (4)
C2—C1—N1	120.4 (5)	C17—C12—N2	118.1 (4)
C6—C1—N1	119.5 (5)	C13—C12—N2	121.8 (4)
C1—C2—C3	121.9 (5)	C12—C13—C14	121.3 (5)
C1—C2—H2	119.0	C12—C13—H13	119.3
C3—C2—H2	119.0	C14—C13—H13	119.3
C2—C3—C4	116.8 (5)	C15—C14—C13	117.7 (5)
C2—C3—C11	121.1 (5)	C15—C14—C22	121.3 (4)
C4—C3—C11	122.1 (4)	C13—C14—C22	120.9 (5)
C5—C4—C3	122.1 (4)	C16—C15—C14	121.3 (4)
C5—C4—Cl1	118.4 (4)	C16—C15—Cl2	118.3 (4)
C3—C4—Cl1	119.5 (4)	C14—C15—Cl2	120.3 (4)
C4—C5—C6	120.3 (5)	C15—C16—C17	120.8 (5)
C4—C5—H5	119.8	C15—C16—H16	119.6
C6—C5—H5	119.8	C17—C16—H16	119.6
C1—C6—C5	118.8 (5)	C12—C17—C16	119.0 (5)
C1—C6—H6	120.6	C12—C17—H17	120.5
C5—C6—H6	120.6	C16—C17—H17	120.5
O1—C7—N1	122.9 (4)	O4—C18—N2	122.9 (5)
O1—C7—C8	122.5 (5)	O4—C18—C19	121.6 (5)
N1—C7—C8	114.6 (4)	N2—C18—C19	115.5 (5)
C9—C8—C7	112.8 (4)	C20—C19—C18	113.1 (4)
C9—C8—H8A	109.0	C20—C19—H19A	109.0
C7—C8—H8A	109.0	C18—C19—H19A	109.0
C9—C8—H8B	109.0	C20—C19—H19B	109.0
C7—C8—H8B	109.0	C18—C19—H19B	109.0
H8A—C8—H8B	107.8	H19A—C19—H19B	107.8
C8—C9—C10	113.5 (5)	C19—C20—C21	114.9 (5)
C8—C9—H9A	108.9	C19—C20—H20A	108.6
C10—C9—H9A	108.9	C21—C20—H20A	108.6
C8—C9—H9B	108.9	C19—C20—H20B	108.6
C10—C9—H9B	108.9	C21—C20—H20B	108.6
H9A—C9—H9B	107.7	H20A—C20—H20B	107.5
O2—C10—O3	123.6 (5)	O5—C21—O6	122.9 (5)
O2—C10—C9	123.5 (5)	O5—C21—C20	123.4 (6)
O3—C10—C9	112.9 (5)	O6—C21—C20	113.7 (5)
C3—C11—H11A	109.5	C14—C22—H22A	109.5
C3—C11—H11B	109.5	C14—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C3—C11—H11C	109.5	C14—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—C2	54.0 (8)	C18—N2—C12—C17	−158.1 (6)
C7—N1—C1—C6	−127.2 (6)	C18—N2—C12—C13	25.7 (9)
C6—C1—C2—C3	0.4 (8)	C17—C12—C13—C14	−1.7 (8)
N1—C1—C2—C3	179.2 (5)	N2—C12—C13—C14	174.4 (5)
C1—C2—C3—C4	0.2 (7)	C12—C13—C14—C15	1.2 (8)
C1—C2—C3—C11	179.5 (5)	C12—C13—C14—C22	−176.6 (5)
C2—C3—C4—C5	−0.8 (8)	C13—C14—C15—C16	−0.2 (8)
C11—C3—C4—C5	179.9 (5)	C22—C14—C15—C16	177.7 (5)
C2—C3—C4—Cl1	−179.4 (4)	C13—C14—C15—Cl2	−177.8 (4)
C11—C3—C4—Cl1	1.3 (7)	C22—C14—C15—Cl2	0.0 (7)
C3—C4—C5—C6	0.8 (8)	C14—C15—C16—C17	−0.4 (8)
Cl1—C4—C5—C6	179.5 (4)	Cl2—C15—C16—C17	177.3 (4)
C2—C1—C6—C5	−0.4 (8)	C13—C12—C17—C16	1.0 (8)
N1—C1—C6—C5	−179.2 (5)	N2—C12—C17—C16	−175.2 (5)
C4—C5—C6—C1	−0.2 (8)	C15—C16—C17—C12	0.0 (9)
C1—N1—C7—O1	3.0 (9)	C12—N2—C18—O4	5.3 (10)
C1—N1—C7—C8	−177.9 (5)	C12—N2—C18—C19	−175.2 (5)
O1—C7—C8—C9	−12.4 (8)	O4—C18—C19—C20	−25.0 (8)
N1—C7—C8—C9	168.6 (5)	N2—C18—C19—C20	155.5 (5)
C7—C8—C9—C10	−178.7 (5)	C18—C19—C20—C21	−179.4 (5)
C8—C9—C10—O2	−2.8 (10)	C19—C20—C21—O5	−7.9 (10)
C8—C9—C10—O3	176.6 (6)	C19—C20—C21—O6	171.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.82 (2)	1.85 (2)	2.668 (5)	176 (7)
N1—H1N···O4ii	0.86 (2)	2.09 (2)	2.934 (5)	169 (5)
O6—H6O···O5iii	0.82 (2)	1.86 (2)	2.685 (6)	177 (8)
N2—H2N···O1	0.85 (2)	2.12 (2)	2.944 (6)	163 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.82 (2)	1.85 (2)	2.668 (5)	176 (7)
N1—H1N⋯O4ii	0.86 (2)	2.09 (2)	2.934 (5)	169 (5)
O6—H6O⋯O5iii	0.82 (2)	1.86 (2)	2.685 (6)	177 (8)
N2—H2N⋯O1	0.85 (2)	2.12 (2)	2.944 (6)	163 (5)

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