N-(3-Methyl­phen­yl)succinimide

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

doi:10.1107/S1600536810015904

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1269

https://doi.org/10.1107/S1600536810015904

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N-(3-Methylphenyl)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 28 April 2010; accepted 29 April 2010; online 8 May 2010)

In the title compound, C₁₁H₁₁NO₂, the dihedral angle between the ring planes is 52.5 (1)°.

Related literature

For related structures, see: Saraswathi et al. (2010a ,b ).

Experimental

Crystal data

C₁₁H₁₁NO₂
M_r = 189.21
Monoclinic, P 2₁ /n
a = 7.7906 (9) Å
b = 6.6015 (8) Å
c = 19.511 (2) Å
β = 100.06 (1)°
V = 988.02 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 299 K
0.32 × 0.16 × 0.14 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 = 0.972, T_max = 0.988
3757 measured reflections
2000 independent reflections
1453 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.168
S = 1.18
2000 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 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: https://doi.org/10.1107/S1600536810015904/ng2766sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015904/ng2766Isup2.hkl

checkCIF report

Comment top

As a part of studying the effect of ring and side chain substitutions on the structures of biologically significant compounds (Saraswathi et al., 2010a,b), the crystal structure of N,N-(3-methylphenyl)succinimide has been determined (Fig.1). In the structure, the molecule is non-planar with the benzene and pyrrolidine rings tilted by 52.5 (1)° with respect to one another, compared to the values of 57.3 (1)° in N,N-(4-methylphenyl)succinimide (Saraswathi et al., 2010a) and 67.7 (1)° jn N,N- (2,3-dimethylphenyl)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 52.6 (2), -127.0 (2), -123.4 (2) and 57.0 (2)°, 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 7.7 (3), -171.5 (2), -2.1 (3) and -178.6 (2)°, respectively.

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

Related literature top

For related structures, see: 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-methylaniline (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-methylaniline. The resultant solid N-(3-methylphenyl)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-methylphenyl)succinamic acid was heated for 2 h and then allowed to cool slowly to room temperature to get the compound, N-(3-methylphenyl)succinimide. The purity of the compound was checked and characterized by its infrared spectra.

Rod 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.

Structure description top

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

For related structures, see: Saraswathi et al. (2010a,b).

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.

1-(3-Methylphenyl)pyrrolidine-2,5-dione top

Crystal data top

C₁₁H₁₁NO₂	F(000) = 400
M_r = 189.21	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1573 reflections
a = 7.7906 (9) Å	θ = 2.6–27.7°
b = 6.6015 (8) Å	µ = 0.09 mm⁻¹
c = 19.511 (2) Å	T = 299 K
β = 100.06 (1)°	Rod, colourless
V = 988.02 (19) Å³	0.32 × 0.16 × 0.14 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2000 independent reflections
Radiation source: fine-focus sealed tube	1453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Rotation method data acquisition using ω and φ scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
T_min = 0.972, T_max = 0.988	k = −8→6
3757 measured reflections	l = −24→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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2000 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₁H₁₁NO₂	V = 988.02 (19) Å³
M_r = 189.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7906 (9) Å	µ = 0.09 mm⁻¹
b = 6.6015 (8) Å	T = 299 K
c = 19.511 (2) Å	0.32 × 0.16 × 0.14 mm
β = 100.06 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2000 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1453 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.988	R_int = 0.020
3757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.18	Δρ_max = 0.17 e Å⁻³
2000 reflections	Δρ_min = −0.18 e Å⁻³
128 parameters

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
C1	0.0804 (2)	0.1090 (2)	0.35080 (8)	0.0418 (4)
C2	0.1645 (2)	−0.0080 (3)	0.40538 (9)	0.0477 (5)
H2	0.1895	−0.1430	0.3977	0.057*
C3	0.2117 (2)	0.0744 (3)	0.47137 (10)	0.0590 (5)
C4	0.1759 (3)	0.2780 (4)	0.48018 (12)	0.0717 (7)
H4	0.2069	0.3364	0.5240	0.086*
C5	0.0957 (3)	0.3947 (3)	0.42550 (12)	0.0699 (6)
H5	0.0744	0.5311	0.4325	0.084*
C6	0.0468 (3)	0.3106 (3)	0.36036 (10)	0.0552 (5)
H6	−0.0082	0.3892	0.3234	0.066*
C7	−0.0722 (2)	−0.1600 (3)	0.27360 (9)	0.0505 (5)
C8	−0.0778 (3)	−0.2276 (4)	0.20019 (10)	0.0679 (6)
H8A	−0.1969	−0.2528	0.1775	0.081*
H8B	−0.0103	−0.3505	0.1987	0.081*
C9	0.0004 (3)	−0.0551 (4)	0.16546 (10)	0.0710 (7)
H9A	0.0894	−0.1044	0.1405	0.085*
H9B	−0.0886	0.0143	0.1329	0.085*
C10	0.0783 (2)	0.0839 (3)	0.22331 (9)	0.0570 (5)
C11	0.2939 (3)	−0.0550 (5)	0.53171 (12)	0.0857 (8)
H11A	0.3588	−0.1625	0.5151	0.103*
H11B	0.2045	−0.1114	0.5541	0.103*
H11C	0.3709	0.0264	0.5644	0.103*
N1	0.02773 (18)	0.0164 (2)	0.28405 (7)	0.0438 (4)
O1	−0.1388 (2)	−0.2413 (2)	0.31764 (8)	0.0682 (5)
O2	0.1681 (2)	0.2311 (3)	0.22030 (8)	0.0867 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0422 (8)	0.0435 (9)	0.0422 (9)	−0.0036 (7)	0.0142 (7)	−0.0011 (7)
C2	0.0468 (9)	0.0519 (10)	0.0461 (10)	−0.0010 (8)	0.0131 (7)	0.0013 (8)
C3	0.0479 (10)	0.0869 (15)	0.0437 (10)	−0.0122 (10)	0.0123 (8)	−0.0003 (10)
C4	0.0711 (13)	0.0912 (17)	0.0566 (12)	−0.0205 (13)	0.0219 (10)	−0.0293 (12)
C5	0.0807 (14)	0.0573 (12)	0.0786 (16)	−0.0142 (12)	0.0330 (12)	−0.0206 (11)
C6	0.0573 (10)	0.0491 (11)	0.0631 (12)	−0.0030 (9)	0.0218 (9)	0.0037 (9)
C7	0.0442 (9)	0.0552 (11)	0.0521 (11)	−0.0006 (8)	0.0086 (8)	−0.0047 (8)
C8	0.0556 (11)	0.0902 (16)	0.0564 (12)	−0.0069 (11)	0.0057 (9)	−0.0211 (11)
C9	0.0618 (12)	0.1086 (18)	0.0423 (11)	0.0053 (12)	0.0086 (9)	−0.0046 (11)
C10	0.0505 (10)	0.0788 (14)	0.0436 (10)	−0.0027 (10)	0.0134 (8)	0.0103 (9)
C11	0.0681 (14)	0.138 (2)	0.0493 (12)	−0.0046 (15)	0.0058 (10)	0.0168 (13)
N1	0.0427 (7)	0.0491 (8)	0.0400 (8)	−0.0009 (6)	0.0085 (6)	0.0025 (6)
O1	0.0757 (9)	0.0631 (9)	0.0698 (9)	−0.0190 (7)	0.0235 (7)	−0.0006 (7)
O2	0.0944 (12)	0.1052 (13)	0.0646 (10)	−0.0348 (10)	0.0254 (9)	0.0154 (9)

Geometric parameters (Å, º) top

C1—C6	1.375 (3)	C7—N1	1.396 (2)
C1—C2	1.385 (2)	C7—C8	1.494 (2)
C1—N1	1.432 (2)	C8—C9	1.507 (3)
C2—C3	1.387 (3)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.389 (3)	C9—C10	1.498 (3)
C3—C11	1.504 (3)	C9—H9A	0.9700
C4—C5	1.375 (3)	C9—H9B	0.9700
C4—H4	0.9300	C10—O2	1.204 (2)
C5—C6	1.378 (3)	C10—N1	1.386 (2)
C5—H5	0.9300	C11—H11A	0.9600
C6—H6	0.9300	C11—H11B	0.9600
C7—O1	1.205 (2)	C11—H11C	0.9600

C6—C1—C2	120.76 (16)	C9—C8—H8A	110.7
C6—C1—N1	120.37 (15)	C7—C8—H8B	110.7
C2—C1—N1	118.87 (15)	C9—C8—H8B	110.7
C1—C2—C3	120.54 (18)	H8A—C8—H8B	108.8
C1—C2—H2	119.7	C10—C9—C8	105.46 (16)
C3—C2—H2	119.7	C10—C9—H9A	110.6
C2—C3—C4	117.90 (19)	C8—C9—H9A	110.6
C2—C3—C11	120.8 (2)	C10—C9—H9B	110.6
C4—C3—C11	121.3 (2)	C8—C9—H9B	110.6
C5—C4—C3	121.34 (19)	H9A—C9—H9B	108.8
C5—C4—H4	119.3	O2—C10—N1	123.72 (18)
C3—C4—H4	119.3	O2—C10—C9	128.29 (17)
C4—C5—C6	120.3 (2)	N1—C10—C9	107.98 (17)
C4—C5—H5	119.8	C3—C11—H11A	109.5
C6—C5—H5	119.8	C3—C11—H11B	109.5
C1—C6—C5	119.10 (19)	H11A—C11—H11B	109.5
C1—C6—H6	120.5	C3—C11—H11C	109.5
C5—C6—H6	120.5	H11A—C11—H11C	109.5
O1—C7—N1	124.49 (16)	H11B—C11—H11C	109.5
O1—C7—C8	127.37 (18)	C10—N1—C7	112.22 (15)
N1—C7—C8	108.13 (16)	C10—N1—C1	124.11 (15)
C7—C8—C9	105.02 (17)	C7—N1—C1	123.56 (13)
C7—C8—H8A	110.7

C6—C1—C2—C3	2.0 (3)	C8—C9—C10—N1	−8.2 (2)
N1—C1—C2—C3	−177.61 (15)	O2—C10—N1—C7	−178.5 (2)
C1—C2—C3—C4	−1.6 (3)	C9—C10—N1—C7	2.2 (2)
C1—C2—C3—C11	176.53 (16)	O2—C10—N1—C1	−2.1 (3)
C2—C3—C4—C5	0.2 (3)	C9—C10—N1—C1	178.57 (15)
C11—C3—C4—C5	−177.9 (2)	O1—C7—N1—C10	−175.92 (19)
C3—C4—C5—C6	0.8 (3)	C8—C7—N1—C10	5.0 (2)
C2—C1—C6—C5	−1.0 (3)	O1—C7—N1—C1	7.7 (3)
N1—C1—C6—C5	178.66 (16)	C8—C7—N1—C1	−171.46 (15)
C4—C5—C6—C1	−0.4 (3)	C6—C1—N1—C10	57.0 (2)
O1—C7—C8—C9	171.10 (19)	C2—C1—N1—C10	−123.42 (19)
N1—C7—C8—C9	−9.8 (2)	C6—C1—N1—C7	−127.04 (18)
C7—C8—C9—C10	10.8 (2)	C2—C1—N1—C7	52.6 (2)
C8—C9—C10—O2	172.5 (2)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₂
M_r	189.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	7.7906 (9), 6.6015 (8), 19.511 (2)
β (°)	100.06 (1)
V (Å³)	988.02 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.16 × 0.14

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	0.972, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	3757, 2000, 1453
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.168, 1.18
No. of reflections	2000
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

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

Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Saraswathi, B. S., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o390. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saraswathi, B. S., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o919. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar