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Volume 65 
Part 10 
Page o2452  
October 2009  

Received 1 August 2009
Accepted 7 September 2009
Online 12 September 2009

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.073
wR = 0.174
Data-to-parameter ratio = 18.9
Details
Open access

N-p-Tolyladamantane-1-carboxamide

Weiwei SiMaa*

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: nysima@126.com

In the crystal of the title compound, C18H23NO, the molecules are linked into chains along the c axis by intermolecular N-H...O hydrogen bonds.

Related literature

For For bond-length data, see: Allen et al. (1987[Allen, F. H. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the synthesis of the title compound, see: Karle et al. (1997[Karle, I. S., Ranganathan, D. & Haridas, D. (1997). J. Am. Chem. Soc. 119, 2777-2783.]); Tadashi et al. (1969[Tadashi Sasaki, (1969). Bull. Chem. Soc. Jpn, 42, 1617-1621.])

[Scheme 1]

Experimental

Crystal data

  • C18H23NO

  • Mr = 269.37

  • Orthorhombic, P c c n

  • a = 30.708 (7) Å

  • b = 9.7927 (2) Å

  • c = 10.0203 (6) Å

  • V = 3013.2 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 298 K

  • 0.50 × 0.30 × 0.30 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.964, Tmax = 0.978

  • 27405 measured reflections

  • 3443 independent reflections

  • 2652 reflections with I > 2[sigma](I)

  • Rint = 0.080
Refinement

  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.174

  • S = 1.16

  • 3443 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.12 2.962 (2) 166
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999[Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ER2072 ).

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

Allen, F. H. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Karle, I. S., Ranganathan, D. & Haridas, D. (1997). J. Am. Chem. Soc. 119, 2777-2783.  [CrossRef] [ChemPort] [ISI]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tadashi Sasaki, (1969). Bull. Chem. Soc. Jpn, 42, 1617-1621.

Acta Cryst (2009). E65, o2452  [ doi:10.1107/S1600536809036101 ]

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