N-(3-Chloro­phen­yl)succinimide

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

doi:10.1107/S1600536811026845

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1977

doi:10.1107/S1600536811026845

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N-(3-Chlorophenyl)succinimide

B. S. Saraswathi,^a Sabine Foro ^b and B. Thimme Gowda ^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 4 July 2011; accepted 5 July 2011; online 9 July 2011)

In the title compound, C₁₀H₈ClNO₂, the chlorobenzene and the essentially planar (r.m.s. deviation = 0.030 Å) pyrrolidine ring are tilted by 59.5 (1)° with respect to one another.

Related literature

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000 ); Gowda et al. (1999 , 2007 ); Saraswathi et al. (2010a ,b ).

Experimental

Crystal data

C₁₀H₈ClNO₂
M_r = 209.62
Orthorhombic, P b c a
a = 12.884 (2) Å
b = 7.173 (1) Å
c = 20.805 (3) Å
V = 1922.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 293 K
0.46 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.849, T_max = 0.968
6087 measured reflections
1755 independent reflections
1163 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.137
S = 1.33
1755 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536811026845/bt5570sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026845/bt5570Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026845/bt5570Isup3.cml

checkCIF report

Comment top

As a part of our studies on the effects of ring and side chain substitutions on the structures and other aspects of biologically significant compounds (Bhat & Gowda, 2000; Gowda et al., 1999, 2007; Saraswathi et al., 2010a,b), the crystal structure of N-(3-chlorophenyl)succinimide has been determined (Fig. 1). In the structure, the molecule is non-planar with the benzene and pyrrolidine rings tilted by 59.5 (1)° with respect to one another, compared to the values of 69.5 (1)° in N-(2-chlorophenyl)- succinimide (Saraswathi et al., 2010a) and 52.5 (1)° in N-(3-methylphenyl)succinimide (Saraswathi et al., 2010b).

The torsional angles of the groups, C2 - C1 - N1 - C7, C6 - C1 - N1 - C7, C2 - C1 - N1 - C10 and C6 - C1 - N1 - C10 in the molecule are -117.5 (5), 61.9 (5), 57.7 (5)° and -123.0 (4), respectively, while the torsional angles of the groups, O1 - C7 - N1 - C1, C8 - C7 - N1 - C1, O2 - C10 - N1 - C1 and C9 - C10 - N1 - C1 are 0.5 (6), -178.4 (4), 2.7 (7) and -177.6 (4)°, respectively.

The packing of molecules into layered chains along a-axis is shown in Fig. 2.

Related literature top

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (1999, 2007); Saraswathi et al. (2010a,b).

Experimental top

The solution of succinic anhydride (0.02 mole) in toluene (25 ml) was treated dropwise with the solution of 3-chloroaniline (0.02 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for one hour and set aside for an additional hour at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 3-chloroaniline. The resultant solid N-(3-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-(3-chlorophenyl)succinamic acid was heated for 2 h and then allowed to cool slowly to room temperature to get the compound, N-(3-chlorophenyl)succinimide. The purity of the compound was checked and characterized by its infrared spectra.

Needle 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 (I), showing the atom labeling. Displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I).

N-(3-Chlorophenyl)succinimide top

Crystal data top

C₁₀H₈ClNO₂	F(000) = 864
M_r = 209.62	D_x = 1.448 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1436 reflections
a = 12.884 (2) Å	θ = 2.8–27.8°
b = 7.173 (1) Å	µ = 0.37 mm⁻¹
c = 20.805 (3) Å	T = 293 K
V = 1922.7 (5) Å³	Needle, colourless
Z = 8	0.46 × 0.12 × 0.09 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1755 independent reflections
Radiation source: fine-focus sealed tube	1163 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Rotation method data acquisition using ω scans	θ_max = 25.4°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→15
T_min = 0.849, T_max = 0.968	k = −6→8
6087 measured reflections	l = −25→22

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.33	w = 1/[σ²(F_o²) + (0.0157P)² + 3.1516P] where P = (F_o² + 2F_c²)/3
1755 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₀H₈ClNO₂	V = 1922.7 (5) Å³
M_r = 209.62	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.884 (2) Å	µ = 0.37 mm⁻¹
b = 7.173 (1) Å	T = 293 K
c = 20.805 (3) Å	0.46 × 0.12 × 0.09 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1755 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1163 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.968	R_int = 0.044
6087 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.33	Δρ_max = 0.32 e Å⁻³
1755 reflections	Δρ_min = −0.46 e Å⁻³
127 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.1240 (3)	0.3985 (6)	0.39944 (19)	0.0406 (10)
C2	0.1122 (3)	0.2512 (6)	0.44197 (19)	0.0427 (10)
H2	0.1035	0.1300	0.4269	0.051*
C3	0.1135 (3)	0.2881 (7)	0.5070 (2)	0.0474 (12)
C4	0.1279 (3)	0.4651 (8)	0.5302 (2)	0.0572 (13)
H4	0.1292	0.4874	0.5743	0.069*
C5	0.1403 (3)	0.6090 (7)	0.4874 (2)	0.0590 (14)
H5	0.1504	0.7294	0.5028	0.071*
C6	0.1381 (3)	0.5785 (6)	0.4213 (2)	0.0489 (12)
H6	0.1459	0.6769	0.3926	0.059*
C7	0.2069 (4)	0.3968 (6)	0.2912 (2)	0.0437 (11)
C8	0.1764 (4)	0.3477 (7)	0.2235 (2)	0.0557 (13)
H8A	0.2260	0.2619	0.2047	0.067*
H8B	0.1725	0.4586	0.1970	0.067*
C9	0.0704 (4)	0.2568 (7)	0.2297 (2)	0.0600 (14)
H9A	0.0203	0.3189	0.2023	0.072*
H9B	0.0738	0.1263	0.2177	0.072*
C10	0.0405 (4)	0.2769 (6)	0.2994 (2)	0.0498 (12)
N1	0.1227 (3)	0.3623 (4)	0.33150 (16)	0.0408 (9)
O1	0.2895 (2)	0.4592 (4)	0.30949 (15)	0.0591 (9)
O2	−0.0397 (3)	0.2302 (5)	0.32476 (16)	0.0706 (10)
Cl1	0.09625 (11)	0.1056 (2)	0.56153 (6)	0.0722 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.033 (2)	0.048 (3)	0.041 (2)	0.002 (2)	−0.0020 (19)	−0.006 (2)
C2	0.042 (3)	0.042 (2)	0.043 (3)	0.004 (2)	−0.001 (2)	−0.006 (2)
C3	0.036 (3)	0.067 (3)	0.039 (3)	0.002 (2)	−0.001 (2)	−0.005 (2)
C4	0.042 (3)	0.085 (4)	0.044 (3)	−0.004 (3)	0.003 (2)	−0.021 (3)
C5	0.041 (3)	0.065 (3)	0.071 (3)	−0.008 (3)	0.006 (3)	−0.035 (3)
C6	0.038 (3)	0.045 (3)	0.064 (3)	−0.004 (2)	0.005 (2)	−0.008 (2)
C7	0.055 (3)	0.035 (2)	0.042 (2)	0.003 (2)	0.000 (2)	0.005 (2)
C8	0.076 (3)	0.052 (3)	0.040 (3)	0.002 (3)	−0.003 (2)	0.007 (2)
C9	0.081 (4)	0.053 (3)	0.046 (3)	−0.006 (3)	−0.018 (3)	0.003 (2)
C10	0.057 (3)	0.039 (3)	0.053 (3)	−0.003 (2)	−0.013 (3)	0.006 (2)
N1	0.044 (2)	0.040 (2)	0.0386 (19)	−0.0028 (17)	−0.0024 (17)	0.0015 (17)
O1	0.053 (2)	0.069 (2)	0.055 (2)	−0.0133 (18)	0.0055 (17)	0.0002 (17)
O2	0.057 (2)	0.087 (3)	0.068 (2)	−0.024 (2)	−0.011 (2)	0.003 (2)
Cl1	0.0824 (9)	0.0924 (10)	0.0418 (6)	0.0078 (8)	0.0035 (7)	0.0082 (7)

Geometric parameters (Å, º) top

C1—C6	1.380 (6)	C7—O1	1.214 (5)
C1—C2	1.387 (6)	C7—N1	1.393 (5)
C1—N1	1.437 (5)	C7—C8	1.505 (6)
C2—C3	1.379 (6)	C8—C9	1.518 (7)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.371 (6)	C8—H8B	0.9700
C3—Cl1	1.746 (5)	C9—C10	1.507 (6)
C4—C5	1.374 (7)	C9—H9A	0.9700
C4—H4	0.9300	C9—H9B	0.9700
C5—C6	1.393 (6)	C10—O2	1.208 (5)
C5—H5	0.9300	C10—N1	1.395 (5)
C6—H6	0.9300

C6—C1—C2	121.2 (4)	N1—C7—C8	108.5 (4)
C6—C1—N1	119.6 (4)	C7—C8—C9	104.9 (4)
C2—C1—N1	119.2 (4)	C7—C8—H8A	110.8
C3—C2—C1	118.6 (4)	C9—C8—H8A	110.8
C3—C2—H2	120.7	C7—C8—H8B	110.8
C1—C2—H2	120.7	C9—C8—H8B	110.8
C4—C3—C2	121.7 (4)	H8A—C8—H8B	108.8
C4—C3—Cl1	118.9 (4)	C10—C9—C8	105.7 (4)
C2—C3—Cl1	119.4 (4)	C10—C9—H9A	110.6
C3—C4—C5	118.9 (4)	C8—C9—H9A	110.6
C3—C4—H4	120.6	C10—C9—H9B	110.6
C5—C4—H4	120.6	C8—C9—H9B	110.6
C4—C5—C6	121.4 (5)	H9A—C9—H9B	108.7
C4—C5—H5	119.3	O2—C10—N1	124.2 (4)
C6—C5—H5	119.3	O2—C10—C9	127.8 (4)
C1—C6—C5	118.3 (4)	N1—C10—C9	108.0 (4)
C1—C6—H6	120.8	C7—N1—C10	112.4 (4)
C5—C6—H6	120.8	C7—N1—C1	123.3 (3)
O1—C7—N1	124.1 (4)	C10—N1—C1	124.1 (4)
O1—C7—C8	127.5 (4)

C6—C1—C2—C3	0.8 (6)	C8—C9—C10—N1	−2.7 (5)
N1—C1—C2—C3	−179.9 (4)	O1—C7—N1—C10	−175.1 (4)
C1—C2—C3—C4	−1.1 (7)	C8—C7—N1—C10	6.0 (5)
C1—C2—C3—Cl1	178.8 (3)	O1—C7—N1—C1	0.5 (6)
C2—C3—C4—C5	0.6 (7)	C8—C7—N1—C1	−178.4 (4)
Cl1—C3—C4—C5	−179.3 (3)	O2—C10—N1—C7	178.3 (4)
C3—C4—C5—C6	0.3 (7)	C9—C10—N1—C7	−2.0 (5)
C2—C1—C6—C5	0.1 (6)	O2—C10—N1—C1	2.7 (7)
N1—C1—C6—C5	−179.2 (4)	C9—C10—N1—C1	−177.6 (4)
C4—C5—C6—C1	−0.6 (7)	C6—C1—N1—C7	61.9 (5)
O1—C7—C8—C9	173.9 (4)	C2—C1—N1—C7	−117.5 (4)
N1—C7—C8—C9	−7.3 (5)	C6—C1—N1—C10	−123.0 (4)
C7—C8—C9—C10	5.9 (5)	C2—C1—N1—C10	57.7 (5)
C8—C9—C10—O2	176.9 (5)

Experimental details

Crystal data
Chemical formula	C₁₀H₈ClNO₂
M_r	209.62
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	12.884 (2), 7.173 (1), 20.805 (3)
V (Å³)	1922.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.46 × 0.12 × 0.09

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	0.849, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	6087, 1755, 1163
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.137, 1.33
No. of reflections	1755
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.46

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

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

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