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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 [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.095
Data-to-parameter ratio = 13.0
Details
Open access

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

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-H...O and C-H...O hydrogen-bonding interactions. An intramolecular C-H...O 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[Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.]). For related structures, see: Mitsui, Nakaema et al. (2008[Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278.]); Mitsui, Noguchi et al. (2009[Mitsui, R., Noguchi, K. & Yonezawa, N. (2009). Acta Cryst. E65, o543.]); Watanabe, Nakaema, Muto et al. (2010[Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o403.]); Watanabe, Nakaema, Nishijima et al. (2010[Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615.]); Hijikata et al. (2010[Hijikata, D., Nakaema, K., Watanabe, S., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o554.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16O5

  • Mr = 336.33

  • Monoclinic, P 21 /c

  • a = 10.8311 (2) Å

  • b = 10.61451 (19) Å

  • c = 15.4492 (3) Å

  • [beta] = 111.728 (1)°

  • V = 1649.95 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.711, Tmax = 0.785

  • 29727 measured reflections

  • 3023 independent reflections

  • 2710 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1...O1i 0.91 (2) 1.83 (2) 2.7320 (15) 173.4 (19)
C7-H7...O3ii 0.93 2.49 3.3215 (19) 150
C15-H15...O2iii 0.93 2.48 3.3152 (16) 149
C17-H17...O5iv 0.93 2.55 3.2821 (18) 136
C9-H9...O2 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[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR2004 (Burla et al., 2005[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA.]); 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

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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [details]
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278.  [CSD] [CrossRef] [details]
Mitsui, R., Noguchi, K. & Yonezawa, N. (2009). Acta Cryst. E65, o543.  [CSD] [CrossRef] [details]
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914-915.  [ISI] [CrossRef] [ChemPort]
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Watanabe, S., Nakaema, K., Muto, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o403.  [CrossRef] [details]
Watanabe, S., Nakaema, K., Nishijima, T., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o615.  [CSD] [CrossRef] [details]


Acta Cryst (2010). E66, o713  [ doi:10.1107/S1600536810006847 ]

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