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

Rukiah, M.; Al-Ktaifani, M.

doi:10.1107/S1600536813004315

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 (C-C) = 0.020 Å
R = 0.016
wR = 0.021
Data-to-parameter ratio = 35.4
Details

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

Mwaffak Rukiah ^a ^* and Mahmoud Al-Ktaifani ^a

^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-HC [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); Sakata et al. (2003); Espinet et al. (2000); Moigno et al. (2002). For the preparation of the bidentate ligand CNCH₂C(CH₃)₂CH₂NC and its organometallic polymeric structures, see: Al-Ktaifani et al. (2008); Rukiah & Al-Ktaifani (2008, 2009); Al-Ktaifani & Rukiah (2010). For chelate complexing, see: Chemin et al. (1996). For the structure of isocyanide, see: Lentz & Preugschat (1993). For practical applications of oganometallic complexes with diisocyanide ligands, see: Fortin et al. (2000). For standard bond-lengths, see: Allen et al. (1987). For background and details of methods applied in powder diffraction, see: Boultif & Louër (2004); Rodriguez-Carvajal (2001); Roisnel & Rodriguez-Carvajal (2001); Le Bail et al. (1988); Toby (2001); Thompson et al. (1987); Finger et al. (1994); Stephens (1999).

Experimental

Crystal data

C₁₆H₁₂N₂
M_r = 232.28
Monoclinic, P 2₁ /c
a = 11.9045 (4) Å
b = 14.6235 (4) Å
c = 7.61672 (15) Å
= 105.483 (2)°
V = 1277.84 (7) Å³
Z = 4
Cu K₁ radiation
= 1.5406 Å
= 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 axis (GSAS; Larson & Von Dreele, 2004)T_min = 0.685, T_max = 0.767
2_min = 4.999°, 2_max = 89.979°, 2_step = 0.02°

Refinement

R_p = 0.016
R_wp = 0.021
R_exp = 0.016
R(F²) = 0.026
² = 1.742
4250 data points
120 parameters
H-atom parameters not refined

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6C14ⁱ	0.991	2.900	3.69 (2)	137.36
C7-H7C14ⁱⁱ	0.986	2.815	3.737 (17)	155.86
C16-H16bC1ⁱⁱⁱ	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); cell refinement: GSAS (Larson & Von Dreele, 2004); data reduction: WinXPOW; program(s) used to solve structure: FOX (Favre-Nicolin & Cerný, 2002); program(s) used to refine structure: GSAS; molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

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

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organic compounds