N-(2-Chloro­phen­yl)succinimide

Saraswathi, B.S.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536810010457

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o921

doi:10.1107/S1600536810010457

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N-(2-Chlorophenyl)succinimide

B. S. Saraswathi,^a B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^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 11 March 2010; accepted 20 March 2010; online 27 March 2010)

In the title compound, C₁₀H₈ClNO₂, the dihedral angle between the aromatic benzene ring and the imide segment is 69.5 (1)°. In the crystal structure, molecules are linked by very weak C—H⋯π interactions along the [001] direction.

Related literature

For our study of the effect of ring and side-chain substitutions on the structures of this class of compounds, see: Gowda et al. (2007 ); Saraswathi et al. (2010a ,b ).

Experimental

Crystal data

C₁₀H₈ClNO₂
M_r = 209.62
Orthorhombic, P c a 2₁
a = 10.616 (1) Å
b = 11.191 (2) Å
c = 8.220 (1) Å
V = 976.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 299 K
0.50 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.840, T_max = 0.869
2417 measured reflections
1600 independent reflections
1500 reflections with I > 2σ(I)
R_int = 0.008

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.072
S = 1.04
1600 reflections
128 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 525 Friedel pairs
Flack parameter: 0.01 (7)

Table 1
C—H⋯π interaction geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D— H⋯ A	D— H	H⋯ A	D⋯ A	D— H⋯ A
C3—H3⋯Cg1ⁱ	0.93	2.93	3.76 (2)	149
Symmetry code: (i) −x + 1, −y, z + $[{1\over 2}]$ .

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 ); 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/S1600536810010457/bx2270sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010457/bx2270Isup2.hkl

checkCIF report

Comment top

The amide moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of ring and side chain substitutions on the structures of this class of compounds (Gowda et al., 2007; Saraswathi et al., 2010a,b), the crystal structure of N,N-(2-chlorophenyl)succinimide has been determined (Fig. 1). In the structure of the title compound, C₁₀H₈ClNO₂, the molecule is non-planar with the benzene and pyrrolidine rings tilted by 69.5 (1)° with respect to one another. In the crystal structure, the molecules are linked by weak C—H···π interactions.

Related literature top

For our study of the effect of ring and side-chain substitutions on the structures of this class of compounds, see: Gowda et al. (2007); Saraswathi et al. (2010a,b).

Experimental top

The solution of succinic anhydride (2.5 g) in toluene (25 ml) was treated dropwise with the solution of 2-chloroaniline (2.5 g) 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-chloroaniline. The resultant solid N-(2-chlorophenyl)succinamic acid 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. N-(2-chlorophenyl)succinamic acid was then heated for 2 hours and then allowed to cool slowly to room temperature to get crystals of N-(2-chlorophenyl)succinimide. The purity of the compound was checked and characterized by its infrared spectra.

The prism like colourless single crystals of the compound used in X-ray diffraction studies were grown in ethanolic solution by a 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. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound.

N-(2-Chlorophenyl)succinimide top

Crystal data top

C₁₀H₈ClNO₂	F(000) = 432
M_r = 209.62	D_x = 1.426 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1700 reflections
a = 10.616 (1) Å	θ = 2.6–27.7°
b = 11.191 (2) Å	µ = 0.36 mm⁻¹
c = 8.220 (1) Å	T = 299 K
V = 976.6 (2) Å³	Prism, colourless
Z = 4	0.50 × 0.48 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1600 independent reflections
Radiation source: fine-focus sealed tube	1500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.008
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→13
T_min = 0.840, T_max = 0.869	k = −13→8
2417 measured reflections	l = −7→10

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	w = 1/[σ²(F_o²) + (0.0446P)² + 0.1451P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.072	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.19 e Å⁻³
1600 reflections	Δρ_min = −0.23 e Å⁻³
128 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.036 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 525 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (7)

Crystal data top

C₁₀H₈ClNO₂	V = 976.6 (2) Å³
M_r = 209.62	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 10.616 (1) Å	µ = 0.36 mm⁻¹
b = 11.191 (2) Å	T = 299 K
c = 8.220 (1) Å	0.50 × 0.48 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1600 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1500 reflections with I > 2σ(I)
T_min = 0.840, T_max = 0.869	R_int = 0.008
2417 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.072	Δρ_max = 0.19 e Å⁻³
S = 1.04	Δρ_min = −0.23 e Å⁻³
1600 reflections	Absolute structure: Flack (1983), 525 Friedel pairs
128 parameters	Absolute structure parameter: 0.01 (7)
1 restraint

Special details top

Experimental. (CrysAlis RED; Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.40098 (5)	0.22415 (4)	0.92831 (9)	0.0664 (2)
O1	0.77333 (15)	0.38146 (14)	0.8513 (2)	0.0691 (5)
O2	0.42907 (15)	0.30911 (14)	0.5374 (2)	0.0625 (4)
N1	0.60155 (12)	0.31896 (14)	0.70608 (18)	0.0386 (4)
C1	0.61026 (16)	0.19473 (17)	0.7438 (2)	0.0388 (4)
C2	0.52257 (16)	0.14047 (17)	0.8445 (3)	0.0438 (4)
C3	0.5306 (2)	0.02002 (18)	0.8789 (3)	0.0507 (5)
H3	0.4708	−0.0160	0.9455	0.061*
C4	0.6275 (2)	−0.04682 (19)	0.8141 (3)	0.0529 (5)
H4	0.6333	−0.1279	0.8375	0.063*
C5	0.71622 (19)	0.00642 (19)	0.7144 (3)	0.0540 (5)
H5	0.7817	−0.0388	0.6712	0.065*
C6	0.70742 (17)	0.12731 (18)	0.6789 (3)	0.0477 (5)
H6	0.7668	0.1631	0.6116	0.057*
C7	0.68670 (17)	0.40365 (17)	0.7621 (2)	0.0437 (4)
C8	0.65005 (18)	0.52249 (17)	0.6916 (3)	0.0481 (5)
H8A	0.7161	0.5527	0.6211	0.058*
H8B	0.6348	0.5802	0.7773	0.058*
C9	0.53041 (17)	0.49950 (18)	0.5953 (3)	0.0495 (5)
H9A	0.4599	0.5421	0.6428	0.059*
H9B	0.5405	0.5251	0.4833	0.059*
C10	0.50941 (17)	0.36713 (18)	0.6038 (3)	0.0429 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0671 (4)	0.0458 (3)	0.0864 (4)	−0.0093 (2)	0.0334 (3)	−0.0081 (3)
O1	0.0631 (9)	0.0671 (10)	0.0771 (11)	−0.0155 (8)	−0.0345 (9)	0.0026 (8)
O2	0.0574 (8)	0.0553 (9)	0.0749 (11)	−0.0085 (7)	−0.0267 (8)	0.0040 (8)
N1	0.0364 (7)	0.0401 (8)	0.0394 (9)	−0.0075 (6)	−0.0032 (7)	0.0028 (7)
C1	0.0378 (8)	0.0416 (9)	0.0370 (10)	−0.0080 (7)	−0.0070 (7)	0.0018 (8)
C2	0.0422 (9)	0.0431 (10)	0.0461 (11)	−0.0087 (8)	0.0032 (8)	−0.0038 (8)
C3	0.0550 (11)	0.0439 (10)	0.0531 (13)	−0.0117 (9)	0.0033 (10)	0.0039 (9)
C4	0.0633 (12)	0.0419 (10)	0.0535 (12)	−0.0019 (9)	−0.0108 (10)	0.0058 (10)
C5	0.0504 (11)	0.0549 (11)	0.0565 (13)	0.0114 (9)	−0.0025 (10)	0.0015 (10)
C6	0.0408 (9)	0.0567 (11)	0.0457 (11)	−0.0003 (8)	−0.0001 (9)	0.0052 (10)
C7	0.0433 (9)	0.0465 (10)	0.0414 (10)	−0.0120 (8)	0.0020 (8)	−0.0039 (8)
C8	0.0518 (10)	0.0430 (10)	0.0495 (11)	−0.0090 (9)	0.0068 (9)	−0.0039 (9)
C9	0.0443 (11)	0.0441 (10)	0.0601 (12)	0.0007 (8)	0.0014 (9)	0.0021 (10)
C10	0.0401 (9)	0.0447 (10)	0.0439 (10)	−0.0024 (8)	0.0001 (9)	0.0005 (8)

Geometric parameters (Å, º) top

Cl1—C2	1.737 (2)	C4—H4	0.9300
O1—C7	1.202 (2)	C5—C6	1.387 (3)
O2—C10	1.203 (2)	C5—H5	0.9300
N1—C7	1.388 (2)	C6—H6	0.9300
N1—C10	1.398 (2)	C7—C8	1.502 (3)
N1—C1	1.427 (2)	C8—C9	1.519 (3)
C1—C6	1.385 (3)	C8—H8A	0.9700
C1—C2	1.386 (3)	C8—H8B	0.9700
C2—C3	1.380 (3)	C9—C10	1.500 (3)
C3—C4	1.379 (3)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.383 (3)

C7—N1—C10	113.08 (16)	C5—C6—H6	120.0
C7—N1—C1	123.41 (15)	O1—C7—N1	124.02 (19)
C10—N1—C1	123.47 (14)	O1—C7—C8	128.07 (18)
C6—C1—C2	119.44 (18)	N1—C7—C8	107.91 (16)
C6—C1—N1	119.70 (16)	C7—C8—C9	105.54 (15)
C2—C1—N1	120.86 (17)	C7—C8—H8A	110.6
C3—C2—C1	120.59 (18)	C9—C8—H8A	110.6
C3—C2—Cl1	119.42 (15)	C7—C8—H8B	110.6
C1—C2—Cl1	119.99 (15)	C9—C8—H8B	110.6
C4—C3—C2	119.79 (19)	H8A—C8—H8B	108.8
C4—C3—H3	120.1	C10—C9—C8	105.50 (16)
C2—C3—H3	120.1	C10—C9—H9A	110.6
C3—C4—C5	120.20 (19)	C8—C9—H9A	110.6
C3—C4—H4	119.9	C10—C9—H9B	110.6
C5—C4—H4	119.9	C8—C9—H9B	110.6
C4—C5—C6	119.92 (19)	H9A—C9—H9B	108.8
C4—C5—H5	120.0	O2—C10—N1	124.13 (18)
C6—C5—H5	120.0	O2—C10—C9	128.10 (19)
C1—C6—C5	120.06 (18)	N1—C10—C9	107.77 (16)
C1—C6—H6	120.0

C7—N1—C1—C6	−69.2 (2)	C4—C5—C6—C1	0.2 (3)
C10—N1—C1—C6	108.2 (2)	C10—N1—C7—O1	−179.95 (19)
C7—N1—C1—C2	110.9 (2)	C1—N1—C7—O1	−2.3 (3)
C10—N1—C1—C2	−71.7 (2)	C10—N1—C7—C8	−0.1 (2)
C6—C1—C2—C3	−0.8 (3)	C1—N1—C7—C8	177.56 (16)
N1—C1—C2—C3	179.19 (17)	O1—C7—C8—C9	−177.3 (2)
C6—C1—C2—Cl1	179.40 (15)	N1—C7—C8—C9	2.9 (2)
N1—C1—C2—Cl1	−0.7 (2)	C7—C8—C9—C10	−4.4 (2)
C1—C2—C3—C4	0.8 (3)	C7—N1—C10—O2	177.3 (2)
Cl1—C2—C3—C4	−179.36 (17)	C1—N1—C10—O2	−0.3 (3)
C2—C3—C4—C5	−0.3 (3)	C7—N1—C10—C9	−2.8 (2)
C3—C4—C5—C6	−0.2 (3)	C1—N1—C10—C9	179.55 (16)
C2—C1—C6—C5	0.2 (3)	C8—C9—C10—O2	−175.7 (2)
N1—C1—C6—C5	−179.71 (18)	C8—C9—C10—N1	4.4 (2)

Experimental details

Crystal data
Chemical formula	C₁₀H₈ClNO₂
M_r	209.62
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	299
a, b, c (Å)	10.616 (1), 11.191 (2), 8.220 (1)
V (Å³)	976.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.50 × 0.48 × 0.40

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.840, 0.869
No. of measured, independent and observed [I > 2σ(I)] reflections	2417, 1600, 1500
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.072, 1.04
No. of reflections	1600
No. of parameters	128
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23
Absolute structure	Flack (1983), 525 Friedel pairs
Absolute structure parameter	0.01 (7)

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

C—H···π interaction geometry ( Å, ° ) top

Cg1 is the centroid of the C1–C6 ring.

D— H··· A	D— H	H··· A	D··· A	D— H··· A
C3—H3···Cg1ⁱ	0.93	2.93	3.76 (2)	149

Symmetry code: (i) -x+1, -y, z+1/2.

Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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