N-(2-Chloro-5-methyl­phen­yl)succinamic acid

Gowda, B.T.; Foro, S.; Chaithanya, U.

doi:10.1107/S1600536811054638

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o221

doi:10.1107/S1600536811054638

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N-(2-Chloro-5-methylphenyl)succinamic acid

B. Thimme Gowda,^a ^* Sabine Foro ^b and U. Chaithanya ^a

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 1 December 2011; accepted 19 December 2011; online 23 December 2011)

In the title compound, C₁₁H₁₂ClNO₃, 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, molecules 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)-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_r = 241.67
Monoclinic, C 2/c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.128
S = 1.19
2322 reflections
152 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻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) $[-x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054638/yk2035sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811054638/yk2035Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are important constituents of many biologically important compounds. As a part of our studies of the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2001; Saraswathi et al., 2011), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2005) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of N-(2-chloro-5-methylphenyl)succinamic acid (I) has been determined (Fig. 1). The conformation of the N—H bond in the amide segment is syn to the ortho–chloro group and anti to the meta–methyl group in the benzene ring, similar to the syn conformation observed between the amide hydrogen and the ortho-Cl and anti conformation between the amide hydrogen and the meta-Cl in the benzene ring of N-(2,5-dichlorophenyl)- succinamic acid (II) (Saraswathi et al., 2011).

Further, the conformations of the amide oxygen and the carboxyl oxygen of the acid segment are syn to each other.

The C═O and O—H bonds of the acid group are in syn position to each other, similar to that observed in (II).

The dihedral angle between the phenyl ring and the amide group is 47.8 (2)°.

The intermolecular O—H···O and N—H···O hydrogen bonds pack the molecules into infinite chains along the b-axis direction (Table 1, Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Related literature top

For our previous studies on the effects of substituents on the structures and other aspects of N-(aryl)-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 top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated with the solution of 2-chloro,5-methylaniline (0.01 mole) also in toluene (20 ml), added dropwise with permanent stirring. The resulting mixture was stirred for about one hour and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with diluted hydrochloric acid to remove the unreacted 2-chloro-5-methyl-aniline. The resultant title compound was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The product was recrystallized to constant melting point from ethanol. The purity of the compound was checked and characterized by its infrared and NMR spectra.

Rod like colorless single crystals used in X-ray diffraction studies were grown from ethanolic solution by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonds shown as dashed lines.

N-(2-Chloro-5-methylphenyl)succinamic acid top

Crystal data top

C₁₁H₁₂ClNO₃	F(000) = 1008
M_r = 241.67	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0268P)² + 6.3165P] where P = (F_o² + 2F_c²)/3
2322 reflections	(Δ/σ)_max = 0.044
152 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₁H₁₂ClNO₃	V = 2322.2 (8) Å³
M_r = 241.67	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 23.780 (5) Å	µ = 0.32 mm⁻¹
b = 4.7784 (7) Å	T = 293 K
c = 23.892 (5) Å	0.42 × 0.10 × 0.08 mm
β = 121.20 (1)°

Data collection top

Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer	2322 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1680 reflections with I > 2σ(I)
T_min = 0.877, T_max = 0.975	R_int = 0.020
4399 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.28 e Å⁻³
2322 reflections	Δρ_min = −0.25 e Å⁻³
152 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x−1/2, −y+3/2, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂ClNO₃
M_r	241.67
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	23.780 (5), 4.7784 (7), 23.892 (5)
β (°)	121.20 (1)
V (Å³)	2322.2 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.42 × 0.10 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.877, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	4399, 2322, 1680
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.128, 1.19
No. of reflections	2322
No. of parameters	152
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2ⁱ	0.832 (19)	1.83 (2)	2.652 (4)	172 (5)
N1—H1N···O1ⁱⁱ	0.858 (18)	2.08 (2)	2.910 (4)	163 (3)

Symmetry codes: (i) −x−1/2, −y+3/2, −z; (ii) x, y+1, z.

Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

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