Benzil bis­(ketazine)

Goutam Kumar Patra; Anindita Mukherjee; Seik Weng Ng

doi:10.1107/S1600536809024489

. 2009 Jul 4;65(Pt 8):o1745. doi: 10.1107/S1600536809024489

Benzil bis(ketazine)

Goutam Kumar Patra ^a, Anindita Mukherjee ^a, Seik Weng Ng ^b,^*

PMCID: PMC2977460 PMID: 21583456

Abstract

The title compound (systematic name: 1,1′,2,2′-tetraphenyl-2,2′-azinodiethanone), C₂₈H₂₀N₂O₂, was obtained by the reaction of benzil monohydrazone with chromium(III) nitrate. The dibenzylidene hydrazine unit is nearly planar (r.m.s. deviation = 0.073 Å) and the two benzoyl units are oriented almost perpendicular to it [dihedral angle = 87.81 (2), 87.81 (2)°]. The molecules are linked into chains along the c axis by C—H⋯O hydrogen bonds and the chains are cross-linked via C—H⋯π interactions involving the benzoyl phenyl rings.

Related literature

For the synthesis of title compound using copper bis(acetylacetonate) as catalyst, see: Ibata & Singh (1994 ▶); Singh (1983 ▶).

Experimental

Crystal data

C₂₈H₂₀N₂O₂
M _r = 416.46
Monoclinic,
a = 8.2875 (2) Å
b = 22.1023 (4) Å
c = 11.6602 (2) Å
β = 97.539 (1)°
V = 2117.37 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 140 K
0.30 × 0.04 × 0.03 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: none
17323 measured reflections
4857 independent reflections
3510 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.107
S = 1.03
4857 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024489/ci2835sup1.cif

e-65-o1745-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024489/ci2835Isup2.hkl

e-65-o1745-Isup2.hkl^{(237.9KB, 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
C1—H1⋯O1ⁱ	0.95	2.24	3.0832 (16)	147
C13—H13⋯Cg1ⁱⁱ	0.95	2.68	3.5705 (16)	157
C18—H18⋯Cg2ⁱⁱⁱ	0.95	2.66	3.5304 (16)	153

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the C1–C6 and C23–C28 rings, respectively.

Acknowledgments

The authors thank Vijaygarh Jyotish Ray College and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Benzil monohydrazone (0.224 g, 1 mmol) was dissolved in acetonitrile (20 ml) and to this was added chromium nitrate nonahyrate (0.40 g, 1 mmol). The greenish yellowish mixture was stirred at room temperature for 6 h. Bright yellow prisms were collected in 40% yield.