N (2 Methylphenyl)acetamide

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organic papers

Acta Cryst.(2007). E63, o1977–o1978 doi:10.1107/S1600536807012998 Gowdaet al. _C

9H11NO

o1977

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

N

-(2-Methylphenyl)acetamide

B. Thimme Gowda,a* Jozef Kozˇı´sˇek,bMiroslav Tokarcˇı´kcand Hartmut Fuessd

a_{Department of Chemistry, Mangalore}

University, Mangalagangotri 574 199, Mangalore, India,b_{Department of Physical}

Chemistry, Slovak University of Technology, Radlinske´ho 9, SK-812 37 Bratislava, Slovak Republic,cDepartment of Chemical Physics, Slovak University of Technology, Radlinske´ho 9, 812 37 Bratislava, Slovak Republic, and

d

Institute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 298 K

Mean(C–C) = 0.005 A˚ Rfactor = 0.070 wRfactor = 0.177

Data-to-parameter ratio = 14.0

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 4 March 2007 Accepted 19 March 2007

In the title compound, C9H11NO, the acetamide unit is slightly

twisted with respect to the 2-methylphenyl substituent. The structure is closely related to that of the unsubstituted N -phenylacetamide with slightly different bond parameters. The conformation of the N—H bond is antito the ortho-methyl substituent in the crystal structure of the title compound.

Comment

In the present work, the structure of N -(2-methylphenyl)-acetamide (2MPA), (I), has been determined as part of a study on the systematization of the crystal structures of acetanilides (Gowdaet al., 2004, 2006, 2007). 2MPA resembles closely the unsubstituted N-(phenyl)-acetamide (PA) and other substi-tuted amides (Brownet al., 1954, 1966; Gowdaet al., 2000a,b, 2001), with slightly different bond parameters. In fact, 2MPA and PA crystallize in the same space group, Pbca. In the structure of 2MPA, the conformation of the N—H bond isanti

to theortho-methyl substituent.

Experimental

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point (375 K). It was characterized by recording its infrared and NMR spectra (Gowdaet al., 2003). Single crystals of the title compound were obtained by the slow evaporation of an ethanolic solution.

Crystal data

C9H11NO

Mr= 149.19

Orthorhombic,Pbca a= 8.9608 (10) A˚

b= 12.4784 (17) A˚

c= 15.012 (2) A˚

V= 1678.6 (4) A˚3

Z= 8

MoKradiation

= 0.08 mm 1

T= 298 (2) K 0.320.150.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: none 10081 measured reflections

1639 independent reflections 895 reflections withI> 2(I)

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Refinement

R[F2> 2(F2)] = 0.070

wR(F2_{) = 0.177}

S= 1.09 1639 reflections

117 parameters

H-atom parameters constrained

max= 0.18 e A˚ 3

min= 0.17 e A˚ 3

All H atoms were positioned geometrically and treated as riding with C—H = 0.93 A˚ (CH aromatic) or 0.96 A˚ (CH3) and N—H =

0.86 A˚ , and with Uiso(H) = 1.2Ueq(CH or NH) and Uiso(H) =

1.5Ueq(CH3).

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED(Oxford Diffraction, 2006); data reduc-tion:CrysAlis RED; program(s) used to solve structure:SHELXS97

(Sheldrick, 1997); program(s) used to refine structure:SHELXL97

(Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows

(Farrugia, 1997); software used to prepare material for publication:

SHELXL97(Sheldrick, 1997),PLATON(Spek, 2003) andWinGX

(Farrugia, 1999).

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for resumption of his research fellowship. JK and MT thank the Grant Agency of the Slovak Republic (Grant No. 1/2449/05).

References

Brown, C. J. (1966).Acta Cryst.21, 442–445.

Brown, C. J. & Corbridge, D. E. C. (1954).Acta Cryst.7, 711–715. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.

Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.

Gowda, B. T., Kozisek, J. & Fuess, H. (2006).Z. Naturforsch. Teil A,61, 588– 594.

Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007).Z. Naturforsch. Teil A,62, 91–100.

Gowda, B. T., Paulus, H. & Fuess, H. (2000a).Z. Naturforsch. Teil A,55, 711– 720.

Gowda, B. T., Paulus, H. & Fuess, H. (2000b).Z. Naturforsch. Teil A,55, 791– 800.

Gowda, B. T., Paulus, H. & Fuess, H. (2001).Z. Naturforsch. Teil A,56, 386– 394.

Gowda, B. T., Svoboda, I. & Fuess, H. (2004).Z. Naturforsch. Teil A,59, 845– 852.

Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003).Z. Naturforsch. Teil A,

58, 801–806.

Oxford Diffraction (2006).CrysAlis CCD,CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.

[image:2.610.315.566.71.235.2]

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Figure 1

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supporting information

sup-1 Acta Cryst. (2007). E63, o1977–o1978

supporting information

Acta Cryst. (2007). E63, o1977–o1978 [https://doi.org/10.1107/S1600536807012998]

N

-(2-Methylphenyl)acetamide

B. Thimme Gowda, Jozef Ko

žíš

ek, Miroslav Tokar

čí

k and Hartmut Fuess

N-(2-Methylphenyl)acetamide

Crystal data

C9H11NO

Mr = 149.19

Orthorhombic, Pbca

Hall symbol: -P 2ac 2ab

a = 8.9608 (10) Å

b = 12.4784 (17) Å

c = 15.012 (2) Å

V = 1678.6 (4) Å3

Z = 8

F(000) = 640

Dx = 1.181 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2695 reflections

θ = 2.3–30.0°

µ = 0.08 mm−1

T = 298 K Prism, colourless 0.32 × 0.15 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Graphite monochromator

Detector resolution: 8.4012 pixels mm-1

ω scans

10081 measured reflections 1639 independent reflections

895 reflections with I > 2σ(I)

Rint = 0.078

θmax = 26.0°, θmin = 4.2°

h = −5→11

k = −15→15

l = −18→18

Refinement

Refinement on F2

Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.070}

wR(F2_{) = 0.177}

S = 1.09 1639 reflections 117 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2₍_F

o2) + (0.0541P)2 + 1.0901P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.015

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Special details

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

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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₎

x y z Uiso*/Ueq

C1 0.0254 (4) 0.9605 (3) 0.1188 (2) 0.0745 (11) H1A −0.0774 0.9533 0.1358 0.089* H1B 0.0430 0.9211 0.0649 0.089* H1C 0.0480 1.0348 0.1092 0.089* C2 0.1220 (3) 0.9178 (2) 0.1908 (2) 0.0507 (8) O3 0.2570 (2) 0.91709 (19) 0.18313 (13) 0.0617 (7) N4 0.0523 (3) 0.8809 (2) 0.26354 (16) 0.0561 (7) H4N −0.0436 0.8820 0.2637 0.067* C5 0.1248 (3) 0.8402 (3) 0.3404 (2) 0.0515 (8) C6 0.2072 (4) 0.7471 (3) 0.3372 (2) 0.0626 (9) C7 0.2717 (5) 0.7132 (3) 0.4163 (3) 0.0850 (12) H7 0.3276 0.6505 0.4162 0.102* C8 0.2564 (4) 0.7683 (4) 0.4942 (3) 0.0851 (12) H8 0.3023 0.7433 0.5458 0.102* C9 0.1743 (4) 0.8595 (3) 0.4963 (2) 0.0754 (11) H9 0.1630 0.8974 0.5492 0.090* C10 0.1079 (3) 0.8953 (3) 0.4196 (2) 0.0606 (9) H10 0.0508 0.9575 0.4209 0.073* C11 0.2227 (5) 0.6830 (3) 0.2542 (3) 0.0935 (13) H11A 0.2584 0.6126 0.2687 0.112* H11B 0.2922 0.7175 0.2150 0.112* H11C 0.1273 0.6775 0.2254 0.112*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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supporting information

sup-3 Acta Cryst. (2007). E63, o1977–o1978

Geometric parameters (Å, º)

C1—C2 1.483 (4) C6—C11 1.486 (5) C1—H1A 0.96 C7—C8 1.360 (6)

C1—H1B 0.96 C7—H7 0.93

C1—H1C 0.96 C8—C9 1.358 (5) C2—O3 1.215 (3) C8—H8 0.93 C2—N4 1.341 (4) C9—C10 1.369 (5) N4—C5 1.417 (4) C9—H9 0.93

N4—H4N 0.86 C10—H10 0.93

C5—C6 1.377 (4) C11—H11A 0.96 C5—C10 1.387 (4) C11—H11B 0.96 C6—C7 1.389 (5) C11—H11C 0.96

C2—C1—H1A 109.5 C6—C7—C8 122.8 (4) C2—C1—H1B 109.5 C6—C7—H7 118.7 H1A—C1—H1B 109.5 C8—C7—H7 118.7 C2—C1—H1C 109.5 C9—C8—C7 119.8 (4) H1A—C1—H1C 109.5 C9—C8—H8 120.1 H1B—C1—H1C 109.5 C7—C8—H8 120.1 O3—C2—N4 122.6 (3) C8—C9—C10 119.3 (4) O3—C2—C1 121.0 (3) C9—C10—C5 120.9 (4) N4—C2—C1 116.4 (3) C8—C9—H9 120.3 C2—N4—C5 125.0 (2) C10—C9—H9 120.3 C2—N4—H4N 117.5 C9—C10—H10 119.5 C5—N4—H4N 117.5 C5—C10—H10 119.5 C6—C5—C10 120.6 (3) C6—C11—H11A 109.5 C6—C5—N4 121.1 (3) C6—C11—H11B 109.5 C10—C5—N4 118.3 (3) H11A—C11—H11B 109.5 C5—C6—C7 116.6 (3) C6—C11—H11C 109.5 C5—C6—C11 122.2 (3) H11A—C11—H11C 109.5 C7—C6—C11 121.1 (3) H11B—C11—H11C 109.5

N (2 Methyl­phen­yl)acetamide

organic papers

o1977

N

-(2-Methylphenyl)acetamide

supporting information

supporting information

N

-(2-Methylphenyl)acetamide

B. Thimme Gowda, Jozef Ko

žíš

ek, Miroslav Tokar

čí

k and Hartmut Fuess

supporting information

N (2 Methylphenyl)acetamide