[Journal logo]

Volume 69 
Part 9 
Page o1384  
September 2013  

Received 16 July 2013
Accepted 26 July 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.062
wR = 0.173
Data-to-parameter ratio = 19.1
Details
Open access

(Z)-N-(2,6-Diisopropylphenyl)-4-nitrobenzimidoyl chloride

aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, and bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
Correspondence e-mail: gelhiti@ksu.edu.sa, kariukib@cardiff.ac.uk

In the title compound, C19H21ClN2O2, the aromatic rings are approximately perpendicular to each other, subtending a dihedral angle of 87.7 (1)°. In the crystal, the 4-nitrophenyl groups of pairs of neighbouring molecules are parallel and oriented head-to-tail with a ring centroid-centroid distance of 3.9247 (12) Å, leading to a [pi]-[pi] interaction between the pair. The faces of each phenyl ring of the 2,6-diisopropylphenyl group interact with two different groups, viz. a chloro group of an adjacent molecule on one side and the edge of the 4-nitrophenyl ring of a second molecule on the other side.

Related literature

For the synthesis and applications of imidoyl chlorides, see: Pelter et al. (1975[Pelter, A., Smith, K., Hutchings, M. G. & Rowe, K. (1975). J. Chem. Soc. Perkin Trans. 1, pp. 129-138.]); Manley & Bilodeau (2002[Manley, P. J. & Bilodeau, M. T. (2002). Org. Lett. 4, 3127-3129.]); Cunico & Pandey (2005[Cunico, R. F. & Pandey, R. K. (2005). J. Org. Chem. 70, 5344-5346.]); Raussukana et al. (2006[Raussukana, Y. V., Khomenko, E. A., Onys'ko, P. P. & Sinitsa, A. D. (2006). Synthesis, pp. 3195-3198.]); Zheng & Alper (2008[Zheng, Z. & Alper, H. (2008). Org. Lett. 10, 4903-4906.]); Kuszpit et al. (2011[Kuszpit, M. R., Wulff, W. D. & Tepe, J. J. (2011). J. Org. Chem. 76, 2913-2919.]). For a related structure of an imidoyl chloride, see: Seidelmann et al. (1998[Seidelmann, O., Beyer, L., Lessmann, F. & Richter, R. (1998). Inorg. Chem. Commun. 1, 472-474.]).

[Scheme 1]

Experimental

Crystal data
  • C19H21ClN2O2

  • Mr = 344.83

  • Triclinic, [P \overline 1]

  • a = 8.2988 (4) Å

  • b = 10.4667 (3) Å

  • c = 10.9665 (3) Å

  • [alpha] = 75.568 (2)°

  • [beta] = 85.411 (2)°

  • [gamma] = 74.145 (2)°

  • V = 887.33 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 150 K

  • 0.35 × 0.20 × 0.15 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.924, Tmax = 0.967

  • 6021 measured reflections

  • 4232 independent reflections

  • 3108 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.173

  • S = 1.06

  • 4232 reflections

  • 222 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C8-C13 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C6-H6...Cg2i 0.95 2.67 3.511 (2) 147
C16-H16B...Cg1ii 0.98 2.79 3.663 (3) 149
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP99 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5293 ).


Acknowledgements

The authors would like to extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding for this research through the research group project RGP-VPP-239.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Cunico, R. F. & Pandey, R. K. (2005). J. Org. Chem. 70, 5344-5346.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kuszpit, M. R., Wulff, W. D. & Tepe, J. J. (2011). J. Org. Chem. 76, 2913-2919.  [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Manley, P. J. & Bilodeau, M. T. (2002). Org. Lett. 4, 3127-3129.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pelter, A., Smith, K., Hutchings, M. G. & Rowe, K. (1975). J. Chem. Soc. Perkin Trans. 1, pp. 129-138.  [CrossRef]
Raussukana, Y. V., Khomenko, E. A., Onys'ko, P. P. & Sinitsa, A. D. (2006). Synthesis, pp. 3195-3198.
Seidelmann, O., Beyer, L., Lessmann, F. & Richter, R. (1998). Inorg. Chem. Commun. 1, 472-474.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Zheng, Z. & Alper, H. (2008). Org. Lett. 10, 4903-4906.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1384  [ doi:10.1107/S1600536813020862 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.