1-Benzoyl­naphthalene-2,7-diyl dibenzoate

Sakamoto, R.; Sasagawa, K.; Hijikata, D.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536812052026

Volume 69
Part 2
Page o210
February 2013

Received 18 December 2012
Accepted 29 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 13.1
Details

1-Benzoylnaphthalene-2,7-diyl dibenzoate

Rei Sakamoto,^a Kosuke Sasagawa,^a Daichi Hijikata,^a Akiko Okamoto ^a ^* and Noriyuki Yonezawa ^a

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
Correspondence e-mail: aokamoto@cc.tuat.ac.jp

In the title compound, C₃₁H₂₀O₅, the phenyl rings of the benzoyloxy and benzoyl groups are twisted away from the naphthalene ring system by 64.27 (6), 73.62 (5) and 80.41 (6)°. In the crystal, C-HO hydrogen bonds and C-H [pi] interactions link the molecules, forming tubular chains parallel to the b axis. The chains are further connected into a three-dimensional network by C-H [pi] interactions and [pi] - [pi] stacking contacts [centroid-centroid distances = 3.622 (10)-3.866 (12) Å].

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009); Okamoto et al. (2011). For structures of closely related compounds, see: Kato et al. (2010); Muto et al. (2011); Nakaema et al. (2008); Sakamoto et al. (2012); Watanabe et al. (2010).

Experimental

Crystal data

C₃₁H₂₀O₅
M_r = 472.47
Monoclinic, P 2₁ /n
a = 16.1318 (3) Å
b = 7.18561 (13) Å
c = 20.7333 (4) Å
= 99.180 (1)°
V = 2372.56 (7) Å³
Z = 4
Cu K radiation
= 0.73 mm^-1
T = 193 K
0.40 × 0.40 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999) T_min = 0.759, T_max = 0.811
40057 measured reflections
4282 independent reflections
3753 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 1.07
4282 reflections
326 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C26-C31 and C5-C10 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3O1ⁱ	0.95	2.30	3.2183 (16)	164
C14-H14O5ⁱⁱ	0.95	2.60	3.520 (2)	164
C29-H29Cg1ⁱⁱⁱ	0.95	2.72	3.6396 (18)	162
C15-H15Cg2ⁱⁱ	0.95	2.78	3.6397 (19)	150
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5035 ).

Acknowledgements

The authors would like to express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Iron and Steel Institute of Japan (ISIJ) Research Promotion Grant, Tokyo, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
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Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659.
Muto, T., Hijikata, D., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2040.
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Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.
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Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sakamoto, R., Sasagawa, K., Hijikata, D., Okamoto, A. & Yonezawa, N. (2012). Acta Cryst. E68, o2454.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615.

organic compounds