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ISSN: 2056-9890

N-(2-Chloro-4-methyl­phen­yl)succinamic acid

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 3 February 2012; accepted 8 February 2012; online 17 February 2012)

In the title compound, C11H12ClNO3, the N—C=O fragment is twisted from the plane of the attached benzene ring by 48.39 (12)°. The carb­oxy­lic acid group is involved in O—H⋯O hydrogen bonding, which links pairs of mol­ecules 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[Gowda, B. T., Foro, S. & Chaithanya, U. (2012). Acta Cryst. E68, o221.]) and references therein.

[Scheme 1]

Experimental

Crystal data
  • C11H12ClNO3

  • Mr = 241.67

  • Triclinic, [P \overline 1]

  • 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[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.881, Tmax = 0.971

  • 3625 measured reflections

  • 2284 independent reflections

  • 1883 reflections with I > 2σ(I)

  • Rint = 0.011

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) x-1, y, z; (ii) -x+1, -y+2, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Recently, we reported the crystal structure of N-(2-chloro-5-methylphenyl)succinamic acid (Gowda et al., 2012). We report here the crystal structure of very closely related N-(2-chloro-4-methylphenyl)succinamic acid, (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related compounds (Gowda et al., 2012, and references therein). The conformations of the amide oxygen and the carboxyl oxygen of the acid segment are anti to each other and both are anti to the H atoms on the adjacent –CH2 group.. The CO and O—H bonds of the acid group are in syn position to each other. The dihedral angle between the benzene ring and the amide group is 48.39 (12)°.

The packing of molecules in the crystal through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1) is shown in Fig. 2.

Related literature top

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

Experimental top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of 2-chloro-4-methylaniline (0.01 mole) also in toluene (20 ml) with constant 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 dilute hydrochloric acid to remove the unreacted 2-chloro-4-methylaniline. The resultant title compound was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It 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 colourless single crystals used in X-ray diffraction studies were grown in ethanol solution by slow evaporation at room temperature.

Refinement top

The H atoms of the NH and OH groups were located in a difference map and restrained to the distances N—H = 0.86 (2) Å and O—H = 0.82 (2) Å, respectively. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å and methylene C—H = 0.97 Å. All H atoms were refined with isotropic displacement parameters set to 1.2–1.5Ueq of the parent atom.

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
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom labelling scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A portion of the crystal packing with hydrogen bonds shown as dashed lines.
N-(2-Chloro-4-methylphenyl)succinamic acid top
Crystal data top
C11H12ClNO3Z = 2
Mr = 241.67F(000) = 252
Triclinic, P1Dx = 1.407 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.8097 (8) ÅCell parameters from 2016 reflections
b = 7.3909 (9) Åθ = 2.5–27.9°
c = 16.147 (2) ŵ = 0.33 mm1
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
Data collection top
Oxford Xcalibur
diffractometer with Sapphire CCD detector
2284 independent reflections
Radiation source: fine-focus sealed tube1883 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 55
Tmin = 0.881, Tmax = 0.971k = 99
3625 measured reflectionsl = 1720
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H 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 parametersΔρmax = 0.28 e Å3
2 restraintsΔρmin = 0.25 e Å3
Crystal data top
C11H12ClNO3γ = 89.57 (1)°
Mr = 241.67V = 570.45 (14) Å3
Triclinic, P1Z = 2
a = 4.8097 (8) ÅMo Kα radiation
b = 7.3909 (9) ŵ = 0.33 mm1
c = 16.147 (2) ÅT = 293 K
α = 85.15 (1)°0.40 × 0.18 × 0.09 mm
β = 85.86 (1)°
Data collection top
Oxford Xcalibur
diffractometer with Sapphire CCD detector
2284 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1883 reflections with I > 2σ(I)
Tmin = 0.881, Tmax = 0.971Rint = 0.011
3625 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0532 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.28 e Å3
2284 reflectionsΔρmin = 0.25 e Å3
152 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7464 (5)0.1423 (3)0.72556 (16)0.0372 (5)
C20.6617 (5)0.1119 (3)0.64792 (16)0.0397 (6)
C30.7600 (6)0.0346 (3)0.60606 (18)0.0479 (6)
H30.69720.05280.55430.057*
C40.9510 (6)0.1542 (4)0.64083 (19)0.0516 (7)
C51.0408 (6)0.1206 (4)0.7175 (2)0.0544 (7)
H51.17280.19760.74120.065*
C60.9412 (5)0.0232 (4)0.76017 (18)0.0465 (6)
H61.00400.04080.81200.056*
C70.7910 (5)0.4059 (3)0.80500 (15)0.0386 (6)
C80.6293 (5)0.5544 (4)0.84608 (17)0.0431 (6)
H8A0.44800.50810.86790.052*
H8B0.59990.65440.80470.052*
C90.7800 (5)0.6234 (4)0.91616 (17)0.0449 (6)
H9A0.78960.52620.96020.054*
H9B0.96960.65440.89550.054*
C100.6475 (5)0.7848 (4)0.95222 (16)0.0441 (6)
C111.0540 (8)0.3163 (4)0.5961 (2)0.0790 (11)
H11A1.04220.29030.53710.095*
H11B0.94090.42010.61510.095*
H11C1.24420.34140.60750.095*
N10.6355 (4)0.2886 (3)0.76914 (14)0.0404 (5)
H1N0.463 (4)0.306 (4)0.7706 (17)0.049*
O11.0450 (3)0.3984 (3)0.80286 (14)0.0594 (6)
O20.4442 (4)0.8624 (3)0.92593 (15)0.0741 (7)
O30.7748 (6)0.8378 (4)1.01368 (17)0.0888 (9)
H3O0.696 (8)0.924 (4)1.035 (2)0.107*
Cl10.42759 (15)0.26087 (10)0.60111 (5)0.0573 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0262 (11)0.0349 (12)0.0506 (14)0.0017 (9)0.0016 (10)0.0079 (10)
C20.0289 (12)0.0395 (13)0.0520 (15)0.0062 (10)0.0033 (10)0.0110 (11)
C30.0484 (15)0.0411 (14)0.0554 (16)0.0046 (12)0.0006 (12)0.0164 (12)
C40.0498 (16)0.0356 (13)0.0685 (19)0.0076 (11)0.0104 (14)0.0118 (12)
C50.0447 (15)0.0441 (15)0.073 (2)0.0164 (12)0.0009 (14)0.0012 (14)
C60.0374 (14)0.0482 (15)0.0540 (16)0.0057 (11)0.0033 (11)0.0056 (12)
C70.0255 (12)0.0447 (13)0.0474 (14)0.0032 (10)0.0044 (10)0.0137 (11)
C80.0266 (12)0.0492 (14)0.0570 (16)0.0044 (10)0.0076 (11)0.0217 (12)
C90.0332 (13)0.0532 (15)0.0516 (15)0.0059 (11)0.0090 (11)0.0192 (12)
C100.0353 (13)0.0533 (15)0.0463 (14)0.0003 (11)0.0036 (11)0.0192 (12)
C110.094 (3)0.0468 (17)0.095 (3)0.0276 (17)0.015 (2)0.0168 (17)
N10.0214 (9)0.0463 (12)0.0568 (13)0.0056 (8)0.0042 (9)0.0223 (10)
O10.0219 (9)0.0689 (13)0.0934 (16)0.0049 (8)0.0080 (9)0.0395 (12)
O20.0578 (13)0.0868 (16)0.0892 (16)0.0282 (12)0.0307 (12)0.0551 (13)
O30.0870 (18)0.0996 (19)0.0954 (19)0.0402 (14)0.0513 (15)0.0655 (16)
Cl10.0547 (4)0.0582 (4)0.0627 (5)0.0234 (3)0.0177 (3)0.0183 (3)
Geometric parameters (Å, º) top
C1—C21.382 (3)C7—C81.512 (3)
C1—C61.395 (3)C8—C91.512 (3)
C1—N11.420 (3)C8—H8A0.9700
C2—C31.387 (3)C8—H8B0.9700
C2—Cl11.736 (2)C9—C101.490 (3)
C3—C41.385 (4)C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.383 (4)C10—O21.215 (3)
C4—C111.513 (4)C10—O31.292 (3)
C5—C61.379 (4)C11—H11A0.9600
C5—H50.9300C11—H11B0.9600
C6—H60.9300C11—H11C0.9600
C7—O11.221 (3)N1—H1N0.839 (17)
C7—N11.343 (3)O3—H3O0.827 (19)
C2—C1—C6117.9 (2)C9—C8—H8A109.2
C2—C1—N1121.0 (2)C7—C8—H8B109.2
C6—C1—N1121.1 (2)C9—C8—H8B109.2
C1—C2—C3121.6 (2)H8A—C8—H8B107.9
C1—C2—Cl1119.42 (18)C10—C9—C8114.3 (2)
C3—C2—Cl1118.9 (2)C10—C9—H9A108.7
C4—C3—C2120.5 (3)C8—C9—H9A108.7
C4—C3—H3119.8C10—C9—H9B108.7
C2—C3—H3119.8C8—C9—H9B108.7
C5—C4—C3117.7 (2)H9A—C9—H9B107.6
C5—C4—C11121.7 (3)O2—C10—O3122.8 (2)
C3—C4—C11120.6 (3)O2—C10—C9124.0 (2)
C6—C5—C4122.2 (3)O3—C10—C9113.2 (2)
C6—C5—H5118.9C4—C11—H11A109.5
C4—C5—H5118.9C4—C11—H11B109.5
C5—C6—C1120.0 (3)H11A—C11—H11B109.5
C5—C6—H6120.0C4—C11—H11C109.5
C1—C6—H6120.0H11A—C11—H11C109.5
O1—C7—N1123.2 (2)H11B—C11—H11C109.5
O1—C7—C8121.7 (2)C7—N1—C1124.10 (19)
N1—C7—C8115.08 (19)C7—N1—H1N117.9 (19)
C7—C8—C9111.9 (2)C1—N1—H1N117.9 (19)
C7—C8—H8A109.2C10—O3—H3O113 (3)
C6—C1—C2—C31.7 (4)C2—C1—C6—C50.8 (4)
N1—C1—C2—C3177.4 (2)N1—C1—C6—C5178.4 (2)
C6—C1—C2—Cl1178.02 (19)O1—C7—C8—C928.9 (4)
N1—C1—C2—Cl12.8 (3)N1—C7—C8—C9153.3 (2)
C1—C2—C3—C41.0 (4)C7—C8—C9—C10173.0 (2)
Cl1—C2—C3—C4178.8 (2)C8—C9—C10—O23.6 (4)
C2—C3—C4—C50.7 (4)C8—C9—C10—O3177.9 (3)
C2—C3—C4—C11178.7 (3)O1—C7—N1—C10.6 (4)
C3—C4—C5—C61.7 (4)C8—C7—N1—C1178.4 (2)
C11—C4—C5—C6177.8 (3)C2—C1—N1—C7132.0 (3)
C4—C5—C6—C11.0 (4)C6—C1—N1—C748.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (2)2.16 (2)2.973 (3)163 (3)
O3—H3O···O2ii0.83 (2)1.85 (2)2.674 (3)172 (4)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC11H12ClNO3
Mr241.67
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)4.8097 (8), 7.3909 (9), 16.147 (2)
α, β, γ (°)85.15 (1), 85.86 (1), 89.57 (1)
V3)570.45 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.40 × 0.18 × 0.09
Data collection
DiffractometerOxford Xcalibur
diffractometer with Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.881, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
3625, 2284, 1883
Rint0.011
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.120, 1.11
No. of reflections2284
No. of parameters152
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1N···O1i0.839 (17)2.159 (18)2.973 (3)163 (3)
O3—H3O···O2ii0.827 (19)1.85 (2)2.674 (3)172 (4)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+2, z+2.
 

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC-BSR one-time Grant to Faculty.

References

First citationGowda, B. T., Foro, S. & Chaithanya, U. (2012). Acta Cryst. E68, o221.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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