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N,N′-Bis(2-methyl­phen­yl)succinamide

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 February 2011; accepted 6 February 2011; online 12 February 2011)

In the title compound, C18H20N2O2, the conformations of the N—H and C=O bonds in the C—NH—C(O)—C segments are anti to each other and the amide O atom is anti to the H atoms attached to the adjacent C atoms. Further, the conformations of the N—H bonds in the amide fragments are anti to the ortho-methyl groups in the adjacent benzene rings. The complete molecule is generated by inversion symmetry. The dihedral angle between the benzene ring and the NH—C(O)—CH2 segment in the two halves of the mol­ecule is 62.1 (2)°. In the crystal, N—H⋯O inter­molecular hydrogen bonds link the mol­ecules into sheet-like infinite chains along the a axis.

Related literature

For our study of the effect of substituents on the structures of this class of compounds, see: Gowda et al. (2010a[Gowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010a). Acta Cryst. E66, o1363.],b[Gowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010b). Acta Cryst. E66, o3037.],c[Gowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010c). Acta Cryst. E66, o3038.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20N2O2

  • Mr = 296.36

  • Monoclinic, P 21 /c

  • a = 11.586 (2) Å

  • b = 7.955 (1) Å

  • c = 8.803 (1) Å

  • β = 101.97 (2)°

  • V = 793.70 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.40 × 0.08 × 0.03 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.]) Tmin = 0.968, Tmax = 0.998

  • 3109 measured reflections

  • 1615 independent reflections

  • 987 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.163

  • S = 0.97

  • 1615 reflections

  • 104 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.85 (2) 1.99 (2) 2.840 (3) 173 (3)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

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[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

The amide moiety is an important constituent of many biologically important compounds. As a part of studying the substituent effects on the structures of this class of compounds (Gowda et al., 2010a,b,c), in the present work, the structure of N,N-Bis(2-methylphenyl)-succinamide has been determined (Fig.1). The conformations of N—H and C=O bonds in the C—NH—C(O)—C segments are anti to each other and the amide O atoms are anti to the H atoms attached to the adjacent C atoms. Further, conformations of the N—H bonds in the amide fragments are anti to the ortho-methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH—C(O)—CH2 segment in the two halves of the molecule is 62.1 (2)°.

Further, C1—N1—C7—C8 and C1a—N1a—C7a—C8a segments are nearly linear and so also the C1—N1—C7—O1 and C1a—N1a—C7a—O1a segments. The torsion angles of C2—C1—N1—C7 and C6—C1—N1—C7 are -64.0 (4)° and 117.6 (3)°.

The series of N—H···O intermolecular hydrogen bonds (Table 1) link the molecules into infinite chains (Fig. 2).

Related literature top

For our study of the effect of substituents on the structures of this class of compounds, see: Gowda et al. (2010a,b,c).

Experimental top

Succinic anhydride (0.01 mol) in toluene (25 ml) was treated drop wise with o-toluidine (0.01 mol) 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 completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove unreacted o-toluidine. The resultant N-(2-methylphenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. The compound was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The N-(2-methylphenyl)succinamic acid obtained was then treated with phosphorous oxychloride and excess of o-toluidine at room temperature with constant stirring. The resultant mixture was stirred for 4 h, kept aside for additional 6 h for completion of the reaction and poured slowly into crushed ice with constant stirring. It was kept aside for a day. The resultant solid, N,N-Bis(2-methylphenyl)- succinamide was filtered under suction, washed thoroughly with water, dilute sodium hydroxide solution and finally with water. It was recrystallized to constant melting point from a mixture of acetone and chloroform. The purity of the compound was checked by elemental analysis, and characterized by its infrared and NMR spectra.

Needle like colorless single crystals used in the X-ray diffraction studies were were grown in a mixture of acetone and chloroform at room temperature.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to the distance N—H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.97 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq 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. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
N,N'-Bis(2-methylphenyl)succinamide top
Crystal data top
C18H20N2O2F(000) = 316
Mr = 296.36Dx = 1.240 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 887 reflections
a = 11.586 (2) Åθ = 2.6–27.6°
b = 7.955 (1) ŵ = 0.08 mm1
c = 8.803 (1) ÅT = 293 K
β = 101.97 (2)°Needle, colourless
V = 793.70 (19) Å30.40 × 0.08 × 0.03 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
1615 independent reflections
Radiation source: fine-focus sealed tube987 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1413
Tmin = 0.968, Tmax = 0.998k = 97
3109 measured reflectionsl = 511
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.5489P]
where P = (Fo2 + 2Fc2)/3
1615 reflections(Δ/σ)max = 0.001
104 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.21 e Å3
Crystal data top
C18H20N2O2V = 793.70 (19) Å3
Mr = 296.36Z = 2
Monoclinic, P21/cMo Kα radiation
a = 11.586 (2) ŵ = 0.08 mm1
b = 7.955 (1) ÅT = 293 K
c = 8.803 (1) Å0.40 × 0.08 × 0.03 mm
β = 101.97 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
1615 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
987 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.998Rint = 0.032
3109 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0661 restraint
wR(F2) = 0.163H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.19 e Å3
1615 reflectionsΔρmin = 0.21 e Å3
104 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
C10.2287 (2)0.4159 (3)0.4527 (3)0.0332 (6)
C20.3283 (2)0.3765 (4)0.3956 (3)0.0375 (7)
C30.3804 (3)0.5058 (4)0.3267 (4)0.0509 (8)
H30.44690.48280.28660.061*
C40.3357 (3)0.6671 (4)0.3168 (4)0.0572 (9)
H40.37120.75050.26820.069*
C50.2395 (3)0.7053 (4)0.3778 (4)0.0544 (9)
H50.21060.81470.37320.065*
C60.1859 (3)0.5800 (4)0.4459 (4)0.0468 (8)
H60.12060.60510.48790.056*
C70.1138 (2)0.1563 (3)0.4500 (3)0.0299 (6)
C80.0525 (2)0.0450 (4)0.5479 (3)0.0356 (7)
H8A0.10820.03750.60130.043*
H8B0.02660.11300.62590.043*
C90.3816 (3)0.2030 (4)0.4074 (4)0.0540 (9)
H9A0.35080.14150.31400.065*
H9B0.36220.14520.49460.065*
H9C0.46580.21180.42120.065*
N10.1685 (2)0.2917 (3)0.5239 (2)0.0355 (6)
H1N0.155 (2)0.310 (3)0.614 (2)0.043*
O10.11453 (17)0.1214 (2)0.31422 (19)0.0414 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0376 (14)0.0357 (16)0.0271 (13)0.0083 (12)0.0085 (11)0.0046 (12)
C20.0355 (14)0.0414 (17)0.0352 (15)0.0055 (13)0.0065 (12)0.0030 (13)
C30.0444 (17)0.061 (2)0.0507 (19)0.0170 (17)0.0179 (15)0.0004 (17)
C40.068 (2)0.047 (2)0.057 (2)0.0246 (17)0.0158 (17)0.0051 (17)
C50.070 (2)0.0332 (18)0.062 (2)0.0114 (16)0.0176 (18)0.0029 (16)
C60.0522 (18)0.0400 (18)0.0511 (19)0.0041 (14)0.0171 (15)0.0092 (15)
C70.0344 (14)0.0312 (14)0.0249 (13)0.0012 (12)0.0078 (10)0.0012 (12)
C80.0444 (16)0.0378 (16)0.0259 (14)0.0092 (12)0.0105 (12)0.0028 (12)
C90.0439 (17)0.058 (2)0.062 (2)0.0057 (16)0.0154 (15)0.0040 (17)
N10.0465 (13)0.0373 (13)0.0262 (11)0.0094 (11)0.0158 (10)0.0048 (10)
O10.0570 (13)0.0437 (12)0.0264 (10)0.0154 (10)0.0157 (9)0.0039 (9)
Geometric parameters (Å, º) top
C1—C21.387 (4)C6—H60.9300
C1—C61.393 (4)C7—O11.229 (3)
C1—N11.427 (3)C7—N11.347 (3)
C2—C31.393 (4)C7—C81.512 (3)
C2—C91.507 (4)C8—C8i1.509 (5)
C3—C41.380 (5)C8—H8A0.9700
C3—H30.9300C8—H8B0.9700
C4—C51.368 (4)C9—H9A0.9600
C4—H40.9300C9—H9B0.9600
C5—C61.376 (4)C9—H9C0.9600
C5—H50.9300N1—H1N0.853 (17)
C2—C1—C6120.8 (3)O1—C7—N1123.6 (2)
C2—C1—N1121.5 (2)O1—C7—C8121.4 (2)
C6—C1—N1117.7 (2)N1—C7—C8115.0 (2)
C1—C2—C3117.3 (3)C8i—C8—C7112.3 (3)
C1—C2—C9122.8 (2)C8i—C8—H8A109.2
C3—C2—C9119.9 (3)C7—C8—H8A109.2
C4—C3—C2121.6 (3)C8i—C8—H8B109.2
C4—C3—H3119.2C7—C8—H8B109.2
C2—C3—H3119.2H8A—C8—H8B107.9
C5—C4—C3120.5 (3)C2—C9—H9A109.5
C5—C4—H4119.8C2—C9—H9B109.5
C3—C4—H4119.8H9A—C9—H9B109.5
C4—C5—C6119.2 (3)C2—C9—H9C109.5
C4—C5—H5120.4H9A—C9—H9C109.5
C6—C5—H5120.4H9B—C9—H9C109.5
C5—C6—C1120.6 (3)C7—N1—C1124.5 (2)
C5—C6—H6119.7C7—N1—H1N115.1 (19)
C1—C6—H6119.7C1—N1—H1N119.6 (19)
C6—C1—C2—C32.3 (4)C2—C1—C6—C52.1 (4)
N1—C1—C2—C3179.4 (2)N1—C1—C6—C5179.5 (3)
C6—C1—C2—C9176.8 (3)O1—C7—C8—C8i30.5 (4)
N1—C1—C2—C91.5 (4)N1—C7—C8—C8i150.9 (3)
C1—C2—C3—C40.6 (4)O1—C7—N1—C13.3 (4)
C9—C2—C3—C4178.6 (3)C8—C7—N1—C1178.1 (2)
C2—C3—C4—C51.4 (5)C2—C1—N1—C764.0 (4)
C3—C4—C5—C61.6 (5)C6—C1—N1—C7117.6 (3)
C4—C5—C6—C10.1 (5)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.85 (2)1.99 (2)2.840 (3)173 (3)
Symmetry code: (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC18H20N2O2
Mr296.36
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.586 (2), 7.955 (1), 8.803 (1)
β (°) 101.97 (2)
V3)793.70 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.08 × 0.03
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.968, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
3109, 1615, 987
Rint0.032
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.163, 0.97
No. of reflections1615
No. of parameters104
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.21

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···O1i0.853 (17)1.991 (18)2.840 (3)173 (3)
Symmetry code: (i) x, y+1/2, 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

First citationGowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010a). Acta Cryst. E66, o1363.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010b). Acta Cryst. E66, o3037.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Tokarčík, M., Rodrigues, V. Z., Kožíšek, J. & Fuess, H. (2010c). Acta Cryst. E66, o3038.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, 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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