2-(2,7-Dimeth­oxy-1-naphtho­yl)benzoic acid

Hijikata, D.; Nakaema, K.; Watanabe, S.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810006847

Volume 66
Part 3
Page o713
March 2010

Received 20 February 2010
Accepted 23 February 2010
Online 27 February 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.095
Data-to-parameter ratio = 13.0
Details

2-(2,7-Dimethoxy-1-naphthoyl)benzoic acid

Daichi Hijikata,^a Kosuke Nakaema,^a Shoji Watanabe,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

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

In the title compound, C₂₀H₁₆O₅, the dihedral angle between the naphthalene ring system and the benzene ring is 67.43 (5)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 82.64 (6) and 41.79 (7)°, respectively, with the naphthalene ring system and the benzene ring. The dihedral angle between the carboxy O-C(=O)-C plane and the benzene ring is 36.38 (7)° and that between the bridging carbonyl C-C(=O)-C plane and the carboxy O-C(=O)-C plane is 51.88 (8)°. The crystal structure is stabilized by intermolecular O-HO and C-HO hydrogen-bonding interactions. An intramolecular C-HO hydrogen bond occurs between a naphthalene H atom and the carbonyl O atom of the carboxy group.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009). For related structures, see: Mitsui, Nakaema et al. (2008); Mitsui, Noguchi et al. (2009); Watanabe, Nakaema, Muto et al. (2010); Watanabe, Nakaema, Nishijima et al. (2010); Hijikata et al. (2010).

Experimental

Crystal data

C₂₀H₁₆O₅
M_r = 336.33
Monoclinic, P 2₁ /c
a = 10.8311 (2) Å
b = 10.61451 (19) Å
c = 15.4492 (3) Å
= 111.728 (1)°
V = 1649.95 (5) Å³
Z = 4
Cu K radiation
= 0.81 mm^-1
T = 296 K
0.60 × 0.60 × 0.30 mm

Data collection

Rigaku R-AXIS- APID diffractometer
Absorption correction: multi-scan (NUMABS; Higashi, 1999) T_min = 0.711, T_max = 0.785
29727 measured reflections
3023 independent reflections
2710 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.095
S = 1.04
3023 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1O1ⁱ	0.91 (2)	1.83 (2)	2.7320 (15)	173.4 (19)
C7-H7O3ⁱⁱ	0.93	2.49	3.3215 (19)	150
C15-H15O2ⁱⁱⁱ	0.93	2.48	3.3152 (16)	149
C17-H17O5^iv	0.93	2.55	3.2821 (18)	136
C9-H9O2	0.93	2.47	3.3850 (16)	169
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: OM2323 ).

Acknowledgements

The authors would express their gratitude to Professor Keiichi Noguchi for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Hijikata, D., Nakaema, K., Watanabe, S., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o554.
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278.
Mitsui, R., Noguchi, K. & Yonezawa, N. (2009). Acta Cryst. E65, o543.
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.
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organic compounds