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Volume 68 
Part 11 
Pages o3169-o3170  
November 2012  

Received 22 September 2012
Accepted 9 October 2012
Online 20 October 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.033
wR = 0.087
Data-to-parameter ratio = 8.6
Details
Open access

2-(Prop-2-enyloxy)benzamide

Bernhard Bugenhagen,a Yosef Al Jasem,b Farah Barkhad,c Bassam al Hindawid and Thies Thiemannd*

aInstitute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany,bDepartment of Chemical Engineering, UAE University, AL Ain, Abu Dhabi, United Arab Emirates,cDepartment of Petroleum Engineering, UAE University, AL Ain, Abu Dhabi, United Arab Emirates, and dDepartment of Chemistry, UAE University, AL Ain, Abu Dhabi, United Arab Emirates
Correspondence e-mail: thies@uaeu.ac.ae

In the title molecule, C10H11NO2, the benzene ring forms dihedral angles of 33.15 (2) and 6.20 (2)° with the mean planes of the amide and propenoxy groups, respectively. The amide -NH2 group is oriented toward the propenoxy substituent and forms a weak intramolecular N-H...O hydrogen bond to the propenoxy O atom. The conformation of the propenoxy group at the Csp2-Csp3 and Csp3-O bonds is synperiplanar and antiperiplanar, respectively. In the crystal, N-H...O hydrogen bonds involving the amide groups generate C(4) and R23(7) motifs that organize the molecules into tapes along the a-axis direction. There are C-H...[pi] interactions between the propenoxy -CH2 group and the aromatic system of neighboring molecules within the tape. The mean planes of the aromatic ring and the propenoxy group belonging to molecules located on opposite sites of the tape form an angle of 83.16 (2)°.

Related literature

For crystal structures of similar compounds, see: Al Jasem et al. (2012[Al Jasem, Y., Hindawi, B. al, Thiemann, T. & White, F. (2012). Acta Cryst. E68, o2639-o2640.]); Pagola & Stephens (2009[Pagola, S. & Stephens, P. W. (2009). Acta Cryst. C65, o583-o586.]); Johnstone et al. (2010[Johnstone, R. D. L., Lennie, A. R., Parker, S. F., Parsons, S., Pidcock, E., Richardson, P. R., Warren, J. E. & Wood, P. A. (2010). CrystEngComm, 12, 1065-1078.]); Pertlik (1990)[Pertlik, F. (1990). Monatsh. Chem. 121, 129-139.]; Sasada et al. (1964[Sasada, Y., Takano, T. & Kakudo, M. (1964). Bull. Chem. Soc. Jpn, 37, 940-946.]). For uses of 2-alkoxybenzamides, see: van de Waterbeemd & Testa (1983[Waterbeemd, H. van de & Testa, B. (1983). J. Med. Chem. 26, 203-207.]); Kusunoki & Harada (1984[Kusunoki, T. & Harada, S. (1984). J. Dermatol. 11, 277-281.]). For the preparation of a related 2-alkoxybenzamide, see: Al Jasem et al. (2012[Al Jasem, Y., Hindawi, B. al, Thiemann, T. & White, F. (2012). Acta Cryst. E68, o2639-o2640.]).

[Scheme 1]

Experimental

Crystal data

  • C10H11NO2

  • Mr = 177.20

  • Orthorhombic, P 21 21 21

  • a = 5.08891 (17) Å

  • b = 11.2542 (4) Å

  • c = 15.8802 (6) Å

  • V = 909.48 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.74 mm-1

  • T = 100 K

  • 0.30 × 0.09 × 0.08 mm
Data collection

  • Agilent SuperNova Atlas diffractometer

  • Absorption correction: Gaussian (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.862, Tmax = 0.951

  • 4718 measured reflections

  • 1079 independent reflections

  • 1016 reflections with I > 2[sigma](I)

  • Rint = 0.025
Refinement

  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.087

  • S = 1.03

  • 1079 reflections

  • 126 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.
D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.90 (2) 2.01 (2) 2.905 (2) 178 (17)
N1-H1B...O1ii 0.89 (3) 2.12 (3) 2.863 (2) 140 (2)
N1-H1B...O2 0.89 (3) 2.31 (2) 2.754 (2) 110.8 (18)
C8-H8B...Cgii 0.99 2.68 3.461 (2) 137
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) within OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97, PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2521 ).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Al Jasem, Y., Hindawi, B. al, Thiemann, T. & White, F. (2012). Acta Cryst. E68, o2639-o2640.  [CSD] [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Johnstone, R. D. L., Lennie, A. R., Parker, S. F., Parsons, S., Pidcock, E., Richardson, P. R., Warren, J. E. & Wood, P. A. (2010). CrystEngComm, 12, 1065-1078.  [ISI] [CSD] [CrossRef] [ChemPort]
Kusunoki, T. & Harada, S. (1984). J. Dermatol. 11, 277-281.  [ChemPort] [PubMed]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Pagola, S. & Stephens, P. W. (2009). Acta Cryst. C65, o583-o586.  [CSD] [CrossRef] [details]
Pertlik, F. (1990). Monatsh. Chem. 121, 129-139.  [CrossRef] [ChemPort]
Sasada, Y., Takano, T. & Kakudo, M. (1964). Bull. Chem. Soc. Jpn, 37, 940-946.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Waterbeemd, H. van de & Testa, B. (1983). J. Med. Chem. 26, 203-207.  [PubMed] [ISI]

Acta Cryst (2012). E68, o3169-o3170   [ doi:10.1107/S1600536812042250 ]

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