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Volume 69 
Part 3 
Pages o412-o413  
March 2013  

Received 30 January 2013
Accepted 13 February 2013
Online 20 February 2013

Key indicators
Powder X-ray study
T = 298 K
Mean [sigma](C-C) = 0.020 Å
R = 0.016
wR = 0.021
Data-to-parameter ratio = 35.4
Details
Open access

Powder X-ray investigation of 4,4'-diisocyano-3,3'-dimethylbiphenyl

aDepartment of Chemistry, Atomic Energy Commission of Syria (AECS), PO Box 6091, Damascus, Syrian Arab Republic
Correspondence e-mail: cscientific@aec.org.sy

The title compound, C16H12N2, was investigated in a powder diffraction study and its structure refined utilizing the Rietveld Method. The molecule has approximate C2 symmetry. The dihedral angle between the rings is 25.6 (7)°. The crystal packing is consolidated by weak C-H...C[triple bond]N hydrogen-bond-like contacts, which lead to the formation of a three-dimensional network. Further stabilization of the crystal structure is achived by weak non-covalent [pi]-[pi] interactions between aromatic rings, with a centroid-centroid distance of 3.839 (8) Å.

Related literature

For disocyano ligands and their coordination complexes, see: Harvey (2001[Harvey, P. D. (2001). Coord. Chem. Rev. 219, 17-52.]); Sakata et al. (2003[Sakata, K., Urabe, K., Hashimoto, M., Yanagi, T., Tsuge, A. & Angelici, R. J. (2003). Synth. React. Inorg. Met. Org. Chem. 33, 11-22.]); Espinet et al. (2000[Espinet, P., Soulantica, K., Charmant, J. P. H. & Orpen, A. G. (2000). Chem. Commun. pp. 915-916.]); Moigno et al. (2002[Moigno, D., Callegas-Gaspar, B., Gil-Rubio, J., Brandt, C. D., Werner, H. & Kiefer, W. (2002). Inorg. Chim. Acta, 334, 355-364.]). For the preparation of the bidentate ligand CNCH2C(CH3)2CH2NC and its organometallic polymeric structures, see: Al-Ktaifani et al. (2008[Al-Ktaifani, M., Rukiah, M. & Shaaban, A. (2008). Pol. J. Chem. 82, 547-557.]); Rukiah & Al-Ktaifani (2008[Rukiah, M. & Al-Ktaifani, M. (2008). Acta Cryst. C64, m170-m172.], 2009[Rukiah, M. & Al-Ktaifani, M. (2009). Acta Cryst. C65, m135-m138.]); Al-Ktaifani & Rukiah (2010[Al-Ktaifani, M. & Rukiah, M. (2010). Acta Cryst. E66, m1555-m1556.]). For chelate complexing, see: Chemin et al. (1996[Chemin, N., D`hardemare, A., Bouquillon, S., Fagret, D. & Vidal, M. (1996). Appl. Radiat. Isot. 47, 479-487.]). For the structure of isocyanide, see: Lentz & Preugschat (1993[Lentz, D. & Preugschat, D. (1993). Acta Cryst. C49, 52-54.]). For practical applications of oganometallic complexes with diisocyanide ligands, see: Fortin et al. (2000[Fortin, D., Drouin, M. & Harvey, P. D. (2000). Inorg. Chem. 39, 2758-2769.]). For standard bond-lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O. & Watson, D. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background and details of methods applied in powder diffraction, see: Boultif & Louër (2004[Boultif, A. & Louër, D. (2004). J. Appl. Cryst. 37, 724-731.]); Rodriguez-Carvajal (2001[Rodriguez-Carvajal, J. (2001). FULLPROF. CEA/Saclay, France.]); Roisnel & Rodriguez-Carvajal (2001[Roisnel, T. & Rodriguez-Carvajal, J. (2001). Mater. Sci. Forum, 378-381, 118-123.]); Le Bail et al. (1988[Le Bail, A., Duroy, H. & Fourquet, J. L. (1988). Mater. Res. Bull. 23, 447-452.]); Toby (2001[Toby, B. H. (2001). J. Appl. Cryst. 34, 210-213.]); Thompson et al. (1987[Thompson, P., Cox, D. E. & Hastings, J. B. (1987). J. Appl. Cryst. 20, 79-83.]); Finger et al. (1994[Finger, L. W., Cox, D. E. & Jephcoat, A. P. (1994). J. Appl. Cryst. 27, 892-900.]); Stephens (1999[Stephens, P. W. (1999). J. Appl. Cryst. 32, 281-289.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12N2

  • Mr = 232.28

  • Monoclinic, P 21 /c

  • a = 11.9045 (4) Å

  • b = 14.6235 (4) Å

  • c = 7.61672 (15) Å

  • [beta] = 105.483 (2)°

  • V = 1277.84 (7) Å3

  • Z = 4

  • Cu K[alpha]1 radiation

  • [lambda] = 1.5406 Å

  • [mu] = 0.56 mm-1

  • T = 298 K

  • flat sheet, 8 × 8 mm

Data collection
  • STOE Transmission STADI P diffractometer

  • Specimen mounting: powder loaded between two Mylar foils

  • Data collection mode: transmission

  • Scan method: step

  • Absorption correction: for a cylinder mounted on the [varphi] axis (GSAS; Larson & Von Dreele, 2004[Larson, A. C. & Von Dreele, R. B. (2004). GSAS. Report LAUR 86-748. LosAlamos National Laboratory, New Mexico, USA.])Tmin = 0.685, Tmax = 0.767

  • 2[theta]min = 4.999°, 2[theta]max = 89.979°, 2[theta]step = 0.02°

Refinement
  • Rp = 0.016

  • Rwp = 0.021

  • Rexp = 0.016

  • R(F2) = 0.026

  • [chi]2 = 1.742

  • 4250 data points

  • 120 parameters

  • H-atom parameters not refined

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...C14i 0.991 2.900 3.69 (2) 137.36
C7-H7...C14ii 0.986 2.815 3.737 (17) 155.86
C16-H16b...C1iii 0.989 2.809 3.73 (2) 154.52
Symmetry codes: (i) -x, -y, -z; (ii) x+1, y, z+1; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: WinXPOW (Stoe & Cie, 1999[Stoe & Cie (1999). WinXPOW. Stoe & Cie, Darmstadt, Germany.]); cell refinement: GSAS (Larson & Von Dreele, 2004[Larson, A. C. & Von Dreele, R. B. (2004). GSAS. Report LAUR 86-748. LosAlamos National Laboratory, New Mexico, USA.]); data reduction: WinXPOW; program(s) used to solve structure: FOX (Favre-Nicolin & Cerný, 2002[Favre-Nicolin, V. & Cerný, R. (2002). J. Appl. Cryst. 35, 734-743.]); program(s) used to refine structure: GSAS; molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5582 ).


Acknowledgements

The authors thank Professors I. Othman, Director General, and. T. Yassine, Head of Chemistry Department, for their support and encouragement.

References

Al-Ktaifani, M. & Rukiah, M. (2010). Acta Cryst. E66, m1555-m1556.  [CrossRef] [details]
Al-Ktaifani, M., Rukiah, M. & Shaaban, A. (2008). Pol. J. Chem. 82, 547-557.  [ChemPort]
Allen, F. H., Kennard, O. & Watson, D. G. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Boultif, A. & Louër, D. (2004). J. Appl. Cryst. 37, 724-731.  [ISI] [CrossRef] [ChemPort] [details]
Chemin, N., D`hardemare, A., Bouquillon, S., Fagret, D. & Vidal, M. (1996). Appl. Radiat. Isot. 47, 479-487.
Espinet, P., Soulantica, K., Charmant, J. P. H. & Orpen, A. G. (2000). Chem. Commun. pp. 915-916.  [CSD] [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Favre-Nicolin, V. & Cerný, R. (2002). J. Appl. Cryst. 35, 734-743.  [ISI] [CrossRef] [ChemPort] [details]
Finger, L. W., Cox, D. E. & Jephcoat, A. P. (1994). J. Appl. Cryst. 27, 892-900.  [CrossRef] [ChemPort] [ISI] [details]
Fortin, D., Drouin, M. & Harvey, P. D. (2000). Inorg. Chem. 39, 2758-2769.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Harvey, P. D. (2001). Coord. Chem. Rev. 219, 17-52.  [ISI] [CrossRef]
Larson, A. C. & Von Dreele, R. B. (2004). GSAS. Report LAUR 86-748. LosAlamos National Laboratory, New Mexico, USA.
Le Bail, A., Duroy, H. & Fourquet, J. L. (1988). Mater. Res. Bull. 23, 447-452.  [CrossRef] [ChemPort] [ISI]
Lentz, D. & Preugschat, D. (1993). Acta Cryst. C49, 52-54.  [CrossRef] [details]
Moigno, D., Callegas-Gaspar, B., Gil-Rubio, J., Brandt, C. D., Werner, H. & Kiefer, W. (2002). Inorg. Chim. Acta, 334, 355-364.  [ISI] [CSD] [CrossRef] [ChemPort]
Rodriguez-Carvajal, J. (2001). FULLPROF. CEA/Saclay, France.
Roisnel, T. & Rodriguez-Carvajal, J. (2001). Mater. Sci. Forum, 378-381, 118-123.  [CrossRef] [ChemPort]
Rukiah, M. & Al-Ktaifani, M. (2008). Acta Cryst. C64, m170-m172.  [CSD] [CrossRef] [details]
Rukiah, M. & Al-Ktaifani, M. (2009). Acta Cryst. C65, m135-m138.  [CrossRef] [details]
Sakata, K., Urabe, K., Hashimoto, M., Yanagi, T., Tsuge, A. & Angelici, R. J. (2003). Synth. React. Inorg. Met. Org. Chem. 33, 11-22.  [CrossRef] [ChemPort]
Stephens, P. W. (1999). J. Appl. Cryst. 32, 281-289.  [ISI] [CrossRef] [ChemPort] [details]
Stoe & Cie (1999). WinXPOW. Stoe & Cie, Darmstadt, Germany.
Thompson, P., Cox, D. E. & Hastings, J. B. (1987). J. Appl. Cryst. 20, 79-83.  [CrossRef] [ChemPort] [ISI] [details]
Toby, B. H. (2001). J. Appl. Cryst. 34, 210-213.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o412-o413   [ doi:10.1107/S1600536813004315 ]

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