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accessN-(2,4-Dimethylphenyl)succinimide
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
In the title compound, C12H13NO2, the dihedral angle between the benzene ring and the imide segment is 85.7 (1)°. In the crystal, the molecules are packed into zigzag chains parallel to the a axis.
Related literature
For our study of the effect of ring and side-chain substitutions on the structures of biologically significant compounds, see: Gowda et al. (2007![[Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91-100.]](../../../../../../logos/arrows/e_arr.gif "Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91-100.")
); Saraswathi et al. (2010a,b).
![[Scheme 1]](vm2021scheme1.gif)
Experimental
Crystal data
|
Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); 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
contains datablocks I, global. DOI: 10.1107/S1600536810009694/vm2021sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536810009694/vm2021Isup2.hkl
The solution of succinic anhydride (0.025 mole) in toluene (25 ml) was treated dropwise with the solution of 2,4-dimethylaniline (0.025 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for one h 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 2,4-dimethylaniline. The resultant solid N-(2,4-dimethylphenyl)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-(2,4-Dimethylphenyl)succinamic acid was heated for 2 h and then allowed to cool slowly to room temperature to get the compound, N-(2,4-dimethylphenyl)succinimide. The purity of the compound was checked and characterized by its infrared spectra.
The 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.
The H atoms of the CH3 groups were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in a difference map and their position refined to C—H = 0.91 (3)–1.06 (3) Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
In the absence of significant effects, Friedel pairs were merged and the Δf"term set to zero.
Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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).
![[Figure 1]](./vm2021fig1thm.gif) | 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. |
![[Figure 2]](./vm2021fig2thm.gif) | Fig. 2. Molecular packing of the title compound. |
| C12H13NO2 | F(000) = 432 |
| Mr = 203.23 | Dx = 1.235 Mg m−3 |
| Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
| a = 7.1461 (7) Å | θ = 5.1–23.4° |
| b = 11.182 (2) Å | µ = 0.68 mm−1 |
| c = 13.676 (2) Å | T = 299 K |
| V = 1092.8 (3) Å3 | Rod, colourless |
| Z = 4 | 0.50 × 0.25 × 0.25 mm |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.065 |
| Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 5.1° |
| Graphite monochromator | h = −3→8 |
| ω/2θ scans | k = −13→13 |
| 2947 measured reflections | l = 0→16 |
| 1152 independent reflections | 3 standard reflections every 120 min |
| 987 reflections with I > 2σ(I) | intensity decay: 1.0% |
| 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0693P)2 + 0.082P] where P = (Fo2 + 2Fc2)/3 |
| 1152 reflections | (Δ/σ)max = 0.011 |
| 157 parameters | Δρmax = 0.12 e Å−3 |
| 0 restraints | Δρmin = −0.17 e Å−3 |
| C12H13NO2 | V = 1092.8 (3) Å3 |
| Mr = 203.23 | Z = 4 |
| Orthorhombic, P212121 | Cu Kα radiation |
| a = 7.1461 (7) Å | µ = 0.68 mm−1 |
| b = 11.182 (2) Å | T = 299 K |
| c = 13.676 (2) Å | 0.50 × 0.25 × 0.25 mm |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.065 |
| 2947 measured reflections | 3 standard reflections every 120 min |
| 1152 independent reflections | intensity decay: 1.0% |
| 987 reflections with I > 2σ(I) |
| R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
| wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | Δρmax = 0.12 e Å−3 |
| 1152 reflections | Δρmin = −0.17 e Å−3 |
| 157 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | −0.0480 (4) | 0.0411 (2) | 0.04393 (17) | 0.0377 (6) | |
| C2 | −0.2151 (4) | −0.0128 (2) | 0.07236 (18) | 0.0410 (6) | |
| C3 | −0.2763 (4) | −0.1082 (2) | 0.0153 (2) | 0.0461 (6) | |
| H3 | −0.400 (5) | −0.144 (3) | 0.034 (2) | 0.055* | |
| C4 | −0.1827 (4) | −0.1484 (2) | −0.06581 (18) | 0.0469 (6) | |
| C5 | −0.0181 (4) | −0.0909 (3) | −0.0921 (2) | 0.0488 (7) | |
| H5 | 0.042 (5) | −0.111 (3) | −0.153 (2) | 0.059* | |
| C6 | 0.0488 (4) | 0.0035 (3) | −0.0372 (2) | 0.0462 (7) | |
| H6 | 0.184 (5) | 0.035 (3) | −0.049 (2) | 0.055* | |
| C7 | −0.0064 (4) | 0.2593 (2) | 0.06994 (18) | 0.0429 (6) | |
| C8 | 0.0891 (5) | 0.3392 (2) | 0.1425 (2) | 0.0483 (7) | |
| H8A | 0.164 (5) | 0.390 (3) | 0.107 (2) | 0.058* | |
| H8B | −0.013 (5) | 0.391 (3) | 0.1798 (19) | 0.058* | |
| C9 | 0.1992 (5) | 0.2553 (3) | 0.2077 (2) | 0.0478 (7) | |
| H9A | 0.182 (5) | 0.264 (3) | 0.273 (3) | 0.057* | |
| H9B | 0.325 (5) | 0.267 (3) | 0.193 (2) | 0.057* | |
| C10 | 0.1393 (4) | 0.1310 (2) | 0.17959 (17) | 0.0427 (6) | |
| C11 | −0.3240 (5) | 0.0311 (3) | 0.1583 (2) | 0.0581 (8) | |
| H11A | −0.3491 | 0.1150 | 0.1507 | 0.070* | |
| H11B | −0.2529 | 0.0185 | 0.2169 | 0.070* | |
| H11C | −0.4400 | −0.0118 | 0.1625 | 0.070* | |
| C12 | −0.2569 (6) | −0.2502 (3) | −0.1256 (2) | 0.0683 (10) | |
| H12A | −0.2704 | −0.3197 | −0.0849 | 0.082* | |
| H12B | −0.1714 | −0.2674 | −0.1779 | 0.082* | |
| H12C | −0.3765 | −0.2288 | −0.1523 | 0.082* | |
| N1 | 0.0217 (3) | 0.14153 (17) | 0.09856 (13) | 0.0376 (5) | |
| O1 | −0.0975 (3) | 0.28747 (18) | −0.00034 (16) | 0.0666 (7) | |
| O2 | 0.1797 (4) | 0.03828 (17) | 0.21710 (15) | 0.0634 (6) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0370 (13) | 0.0333 (12) | 0.0428 (12) | −0.0018 (10) | −0.0027 (11) | 0.0014 (10) |
| C2 | 0.0362 (13) | 0.0422 (12) | 0.0447 (12) | −0.0015 (11) | 0.0014 (12) | 0.0064 (10) |
| C3 | 0.0418 (14) | 0.0410 (13) | 0.0554 (14) | −0.0095 (12) | −0.0025 (13) | 0.0064 (11) |
| C4 | 0.0557 (16) | 0.0388 (12) | 0.0462 (13) | −0.0038 (13) | −0.0092 (13) | 0.0017 (11) |
| C5 | 0.0505 (15) | 0.0511 (15) | 0.0448 (13) | 0.0000 (13) | 0.0040 (14) | −0.0067 (12) |
| C6 | 0.0380 (14) | 0.0486 (15) | 0.0521 (14) | −0.0044 (12) | 0.0055 (13) | −0.0029 (11) |
| C7 | 0.0385 (13) | 0.0368 (12) | 0.0534 (13) | 0.0039 (11) | −0.0018 (13) | −0.0007 (11) |
| C8 | 0.0501 (16) | 0.0375 (13) | 0.0571 (15) | −0.0026 (13) | −0.0003 (15) | −0.0054 (12) |
| C9 | 0.0444 (15) | 0.0526 (15) | 0.0463 (14) | −0.0084 (14) | −0.0032 (14) | −0.0062 (12) |
| C10 | 0.0390 (13) | 0.0472 (14) | 0.0419 (12) | −0.0021 (12) | −0.0006 (11) | −0.0001 (11) |
| C11 | 0.0522 (17) | 0.0627 (17) | 0.0595 (16) | −0.0011 (16) | 0.0141 (15) | −0.0013 (14) |
| C12 | 0.083 (3) | 0.0562 (17) | 0.0657 (17) | −0.0156 (18) | −0.0154 (19) | −0.0090 (15) |
| N1 | 0.0353 (11) | 0.0353 (10) | 0.0422 (10) | −0.0008 (9) | −0.0031 (9) | −0.0015 (8) |
| O1 | 0.0745 (15) | 0.0501 (12) | 0.0754 (12) | 0.0086 (11) | −0.0306 (13) | 0.0057 (11) |
| O2 | 0.0710 (15) | 0.0525 (12) | 0.0665 (12) | −0.0038 (11) | −0.0214 (12) | 0.0138 (10) |
| C1—C6 | 1.373 (4) | C8—C9 | 1.514 (4) |
| C1—C2 | 1.393 (4) | C8—H8A | 0.92 (3) |
| C1—N1 | 1.438 (3) | C8—H8B | 1.06 (3) |
| C2—C3 | 1.392 (4) | C9—C10 | 1.505 (4) |
| C2—C11 | 1.493 (4) | C9—H9A | 0.91 (3) |
| C3—C4 | 1.372 (4) | C9—H9B | 0.93 (4) |
| C3—H3 | 1.00 (3) | C10—O2 | 1.192 (3) |
| C4—C5 | 1.388 (4) | C10—N1 | 1.396 (3) |
| C4—C12 | 1.498 (4) | C11—H11A | 0.9600 |
| C5—C6 | 1.381 (4) | C11—H11B | 0.9600 |
| C5—H5 | 0.97 (3) | C11—H11C | 0.9600 |
| C6—H6 | 1.04 (3) | C12—H12A | 0.9600 |
| C7—O1 | 1.203 (3) | C12—H12B | 0.9600 |
| C7—N1 | 1.388 (3) | C12—H12C | 0.9600 |
| C7—C8 | 1.499 (4) | ||
| C6—C1—C2 | 121.6 (2) | H8A—C8—H8B | 108 (3) |
| C6—C1—N1 | 119.0 (2) | C10—C9—C8 | 105.9 (2) |
| C2—C1—N1 | 119.3 (2) | C10—C9—H9A | 108 (2) |
| C1—C2—C3 | 116.4 (2) | C8—C9—H9A | 116 (2) |
| C1—C2—C11 | 121.6 (2) | C10—C9—H9B | 110 (2) |
| C3—C2—C11 | 122.0 (2) | C8—C9—H9B | 106.8 (19) |
| C4—C3—C2 | 123.5 (3) | H9A—C9—H9B | 109 (3) |
| C4—C3—H3 | 120.1 (17) | O2—C10—N1 | 124.1 (2) |
| C2—C3—H3 | 116.3 (17) | O2—C10—C9 | 128.7 (2) |
| C3—C4—C5 | 118.1 (2) | N1—C10—C9 | 107.2 (2) |
| C3—C4—C12 | 121.2 (3) | C2—C11—H11A | 109.5 |
| C5—C4—C12 | 120.7 (3) | C2—C11—H11B | 109.5 |
| C6—C5—C4 | 120.4 (3) | H11A—C11—H11B | 109.5 |
| C6—C5—H5 | 120 (2) | C2—C11—H11C | 109.5 |
| C4—C5—H5 | 120 (2) | H11A—C11—H11C | 109.5 |
| C1—C6—C5 | 120.0 (3) | H11B—C11—H11C | 109.5 |
| C1—C6—H6 | 119.3 (16) | C4—C12—H12A | 109.5 |
| C5—C6—H6 | 119.7 (16) | C4—C12—H12B | 109.5 |
| O1—C7—N1 | 123.5 (2) | H12A—C12—H12B | 109.5 |
| O1—C7—C8 | 128.3 (2) | C4—C12—H12C | 109.5 |
| N1—C7—C8 | 108.2 (2) | H12A—C12—H12C | 109.5 |
| C7—C8—C9 | 104.9 (2) | H12B—C12—H12C | 109.5 |
| C7—C8—H8A | 106.3 (19) | C7—N1—C10 | 113.0 (2) |
| C9—C8—H8A | 113 (2) | C7—N1—C1 | 122.9 (2) |
| C7—C8—H8B | 109.2 (18) | C10—N1—C1 | 123.7 (2) |
| C9—C8—H8B | 114.2 (15) | ||
| C6—C1—C2—C3 | 1.2 (4) | C7—C8—C9—C10 | −8.4 (3) |
| N1—C1—C2—C3 | 178.9 (2) | C8—C9—C10—O2 | −173.7 (3) |
| C6—C1—C2—C11 | −177.6 (2) | C8—C9—C10—N1 | 6.0 (3) |
| N1—C1—C2—C11 | 0.0 (4) | O1—C7—N1—C10 | 177.2 (3) |
| C1—C2—C3—C4 | −0.9 (4) | C8—C7—N1—C10 | −4.6 (3) |
| C11—C2—C3—C4 | 178.0 (3) | O1—C7—N1—C1 | 3.2 (4) |
| C2—C3—C4—C5 | 0.1 (4) | C8—C7—N1—C1 | −178.6 (2) |
| C2—C3—C4—C12 | −178.9 (3) | O2—C10—N1—C7 | 178.8 (3) |
| C3—C4—C5—C6 | 0.5 (4) | C9—C10—N1—C7 | −0.9 (3) |
| C12—C4—C5—C6 | 179.5 (3) | O2—C10—N1—C1 | −7.2 (4) |
| C2—C1—C6—C5 | −0.7 (4) | C9—C10—N1—C1 | 173.0 (2) |
| N1—C1—C6—C5 | −178.4 (3) | C6—C1—N1—C7 | 80.0 (3) |
| C4—C5—C6—C1 | −0.2 (4) | C2—C1—N1—C7 | −97.8 (3) |
| O1—C7—C8—C9 | −173.9 (3) | C6—C1—N1—C10 | −93.4 (3) |
| N1—C7—C8—C9 | 8.1 (3) | C2—C1—N1—C10 | 88.9 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C12H13NO2 |
| Mr | 203.23 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 299 |
| a, b, c (Å) | 7.1461 (7), 11.182 (2), 13.676 (2) |
| V (Å3) | 1092.8 (3) |
| Z | 4 |
| Radiation type | Cu Kα |
| µ (mm−1) | 0.68 |
| Crystal size (mm) | 0.50 × 0.25 × 0.25 |
| Data collection | |
| Diffractometer | Enraf–Nonius CAD-4 diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 2947, 1152, 987 |
| Rint | 0.065 |
| (sin θ/λ)max (Å−1) | 0.597 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.113, 1.06 |
| No. of reflections | 1152 |
| No. of parameters | 157 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.12, −0.17 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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
Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100. CAS Google Scholar
Saraswathi, B. S., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o325. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saraswathi, B. S., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o390. Web of Science CSD 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
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
As a part of studying the effect of ring and side chain substitutions on the structures of biologically significant compounds (Gowda et al., 2007; Saraswathi et al., 2010a,b), the crystal structure of N,N-(2,4-dimethylphenyl)succinimide has been determined (Fig. 1). The dihedral angle between the benzene ring and the imide segment in the molecule is 85.7 (1)°.
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 -97.8 (3)°, 80.0 (3)°, 88.9 (3)° and -93.4 (3)°, 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 3.2 (4)°, -178.6 (2)°, -7.2 (4)° and 173.0 (2)°, respectively.
The packing of molecules into zigzag chains is shown in Fig.2.