2,2′-o-Phenyl­enediacetonitrile

Yang Li; Guoxiong Hua; Alexandra M Z Slawin; J Derek Woollins

doi:10.1107/S1600536809041506

. 2009 Oct 17;65(Pt 11):o2757. doi: 10.1107/S1600536809041506

2,2′-o-Phenylenediacetonitrile

Yang Li ^a, Guoxiong Hua ^a, Alexandra M Z Slawin ^a, J Derek Woollins ^a,^*

PMCID: PMC2971004 PMID: 21578351

Abstract

In the title compound, NCCH₂C₆H₄CH₂CN, the bond lengths and angles are within normal ranges. The benzene ring makes dihedral angles of 4.94 (8) and 77.04 (8)° with the C—C—C—N mean planes. Weak non-conventional C—H⋯N hydrogen bonds are effective in the stabilization of the crystal structure. The weak C—H⋯N contacts form antiparallel chains running in the a + c direction, and ring systems with two N-atom acceptors and four H-atom donors.

Related literature

For reactions of Woollins’ Reagent see: Gray et al. (2005 ▶); Hua et al. (2006 ▶, 2009 ▶); Hua & Woollins (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₀H₈N₂
M _r = 156.18
Monoclinic,
a = 8.3882 (18) Å
b = 8.1605 (15) Å
c = 11.993 (2) Å
β = 101.890 (6)°
V = 803.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ▶) T _min = 0.977, T _max = 0.988
5271 measured reflections
1660 independent reflections
1330 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.133
S = 1.09
1660 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041506/si2203sup1.cif

e-65-o2757-sup1.cif^{(14.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041506/si2203Isup2.hkl

e-65-o2757-Isup2.hkl^{(80.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N1ⁱ	0.99	2.57	3.5605 (18)	176
C9—H9B⋯N1ⁱⁱ	0.99	2.56	3.5210 (17)	165

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors are grateful to the University of St Andrews and the Engineering and Physical Science Research Council (EPRSC, UK) for financial support.

supplementary crystallographic information

Comment

Recently, we have continued our studies exploring the reactivity of Woollins reagent towards different organic substituents (Gray et al. 2005, Hua et al. 2006 and 2009; Hua & Woollins 2009). Thereby 2,2'-(1,2-phenylene)diacetonitrile represents one of the starting materials. Single crystals of 2,5-dihydroxybenzaldehyde for X-ray crystallographic analysis were obtained by recrystallization from dichloromethane-hexane solution.

The bond lengths (Allen et al., 1987) and angles are within normal ranges.The benzene ring makes the dihedral angles of 4.94 (8) and 77.04 (8)° with the mean planes of C1—C7—C8—N1 and C2—C9—C10—N2 respectively. The antiparallel chains running in a+cdirection are generated through the weak C—H···N contacts, glide plane and inversinon symmetry operations[see Fig. 2 and Table 1]. Inversion symmetry forms also C—H···N ring systems consisting of two N acceptors and four H atom donors,where the centroid-centroid distance between the inversion-related benzene ring planes is 3.6809 (10) Å, the perpendicular plane to plane distance is 3.364 Å, and the slippage between the planes is 1.495 Å.

Experimental

Commercially available 2,2'-(1,2-phenylene)diacetonitrile was recrystallized from dichloromethane-hexane.