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Volume 69 
Part 8 
Page o1201  
August 2013  

Received 14 June 2013
Accepted 30 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.100
Data-to-parameter ratio = 18.4
Details
Open access

(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India,bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India,dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

The title compound C28H22O2, basically consists of three ring systems, viz. a central benzene ring, with a lateral napthalene group to which it subtends a dihedral angle of 66.56 (4)° and a tetrahydropyran ring exhibiting a half-chair conformation. The molecular structure is stabilized by a weak intramolecular C-H...O interaction, while the crystal packing features weak C-H...[pi] contacts.

Related literature

For the biological activity of diketones, see: Bennett et al. (1999[Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.]); Sugawara et al. (2001[Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.]). For related structures, see: Jagadeesan et al. (2011[Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.], 2013[Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o26.])

[Scheme 1]

Experimental

Crystal data
  • C28H22O2

  • Mr = 390.46

  • Orthorhombic, P 21 21 21

  • a = 10.5625 (5) Å

  • b = 13.6374 (8) Å

  • c = 14.4927 (8) Å

  • V = 2087.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.985, Tmax = 0.989

  • 13047 measured reflections

  • 4998 independent reflections

  • 3511 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.100

  • S = 1.03

  • 4998 reflections

  • 272 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12-C17 ring.

D-H...A D-H H...A D...A D-H...A
C16-H16...O1 0.93 2.29 2.856 (2) 118
C4-H4...Cg3i 0.93 2.54 3.419 (1) 159
C25-H25A...Cg3ii 0.97 2.94 3.849 (5) 157
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2509 ).


References

Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2011). Acta Cryst. E67, o3036.  [CSD] [CrossRef] [IUCr Journals]
Jagadeesan, G., Sethusankar, K., Sivasakthikumaran, R. & Mohanakrishnan, A. K. (2013). Acta Cryst. E69, o26.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sugawara, Y., Kawai, H., Matsumoto, T., Okano, K. & Takizawa, S. (2001). US Patent No. 6184245 B1.


Acta Cryst (2013). E69, o1201  [ doi:10.1107/S1600536813018035 ]

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