2,2′-Bi[6,6′-dimethyl­dibenzo[d,f][1,3]dioxepine]

Zhang, H.-Q.; Bao-Li; Yang, G.-D.; Ma, Y.-G.

doi:10.1107/S1600536808009094

Volume 64
Part 5
Page o817
May 2008

Received 31 March 2008
Accepted 3 April 2008
Online 10 April 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.126
Data-to-parameter ratio = 17.4
Details

2,2'-Bi[6,6'-dimethyldibenzo[d,f][1,3]dioxepine]

Hai-Quan Zhang,^a ^* Bao-Li,^b Guang-Di Yang ^b and Yu-Guang Ma ^b

^aState Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, People's Republic of China, and ^bState Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: hqzhang@ysu.edu.cn

The title compound, C₃₀H₂₆O₄, is a dimer of 6,6'-dimethyldibenzo[d,f][1,3]dioxepine linked by formation of a C-C bond in the para position with respect to one O atom. The dimer is arranged around an inversion centre. As is usually observed in related compounds, the dibenzo group is twisted, the two benzene rings making a dihedral angle of 41.56 (9)°. The seven-membered ring exhibits a twisted conformation.

Related literature

For related literature, see: Colon & Kelsey (1986); McCullough (1998); Samdal & Bastiansen (1985); Silcox Yoder & Zuckerman (1967); Suzuki (1959); Harada et al. (1994, 1997); Pajunen et al. (1996).

Experimental

Crystal data

C₃₀H₂₆O₄
M_r = 450.51
Monoclinic, P 2₁ /c
a = 13.2938 (16) Å
b = 7.3200 (17) Å
c = 12.7067 (11) Å
= 103.61 (3)°
V = 1201.8 (4) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.18 × 0.13 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.985, T_max = 0.990
5035 measured reflections
2712 independent reflections
1170 reflections with I > 2(I)
R_int = 0.072

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.126
S = 0.81
2712 reflections
156 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.17 e Å^-3

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku , 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2334 ).

Acknowledgements

The authors acknowledge financial support from the National Science Foundation of China (20125421, 90101026, 50303007 and 60207003) and by the Ministry of Science and Technology of China (2002CB6134003 and 2003CB3147032).

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
Colon, I. & Kelsey, D. R. (1986). J. Org. Chem. 51, 2627-2637.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harada, T., Ueda, S., Tuyet, T. M. T., Inoue, A., Fujita, K., Takeuchi, M., Ogawa, N., Oku, A. & Shiro, M. (1997). Tetrahedron, 53, 16663-16678.
Harada, T., Ueda, S., Yoshida, T., Inoue, A., Takeuchi, M., Ogawa, N., Oku, A. & Shiro, M. (1994). J. Org. Chem. 59, 7575-7576.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
McCullough, R. D. (1998). Adv. Mater. 10, 93-116.
Molecular Structure Corporation & Rigaku (2002). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Pajunen, A., Karhunen, P. & Brunow, G. (1996). Acta Cryst. C52, 1815-1817.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Samdal, S. & Bastiansen, O. (1985). J. Mol. Struct. 128, 115-125.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Silcox Yoder, C. M. & Zuckerman, J.J. (1967). J. Heterocycl. Chem. 4, 166-167.
Suzuki, H. (1959). Bull. Chem. Soc. Jpn, 32, 1340-1350.

organic compounds