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Volume 69 
Part 7 
Pages o1011-o1012  
July 2013  

Received 21 April 2013
Accepted 27 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.041
wR = 0.110
Data-to-parameter ratio = 12.2
Details
Open access

rac-3-(4-Hydroxybenzyl)chroman-4-one

aDepartment of Chemistry, Chemistry Research Centre (Affiliated to Kuvempu University), SSMRV Degree College, Jayanagar 4th T Block, Bangalore 560 041, India,bDepartment of Chemistry, KMC International Centre, Manipal University, Manipal 576 104, India,cDepartment of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal University, Manipal 576 104, India, and dDepartment of Chemistry, Jnana Sahyadri, Kuvempu University, Shankargatta 577 451, India
Correspondence e-mail: girija.shivakumar@rediffmail.com

In the racemic title compound, C16H14O3, the ring of the 4-hydroxybenzyl substituent group forms a dihedral angle of 80.12 (12)° with the benzene ring of the chromanone system. Two C atoms of the pyranone ring and the H atoms on the benzyl [alpha]-C atom are disordered over two sites, with site-occupation factors of 0.818 (8) and 0.182 (8). The crystal structure is stabilized by O-H...O hydrogen bonds, which form parallel one-dimensional zigzag chains down the c axis and are interconnected by both methine C-H...O hydrogen bonds and weak aromatic C-H...[pi] interactions, giving a sheet structure lying parallel to [011].

Related literature

For general background on the properties of isoflavanones (derivatives of 3-benzyl-4H-chromen-4-one), see: Klymchenko et al. (2003[Klymchenko, A. S., Pivovarenko, V. G. & Demchenko, A. P. (2003). Spectrochim. Acta Part A, 59, 787-792.]); Sengupta & Kasha (1979[Sengupta, P. K. & Kasha, M. (1979). Chem. Phys. Lett. 68, 382-385.]). For related structures, see: Etter et al. (1986[Etter, M. C., Urbanczyk-Lipkowska, Z., Baer, S. & Barbara, P. F. (1986). J. Mol. Struct. 144, 155-167.]); Waller et al. (2003[Waller, M. P., Hibbs, D. E., Overgaard, J., Hanrahan, J. R. & Hambley, T. W. (2003). Acta Cryst. E59, o767-o768.]); Wera et al. (2011[Wera, M., Pivovarenko, V. G. & Blazejowski, J. (2011). Acta Cryst. E67, o264-o265.]); Shalini et al. (2013[Shalini, S., Girija, C. R., Simon, L., Srinivasan, K. K., Venkatesha, T. V. & Jotani, M. M. (2013). Acta Cryst. E69, o241.]). For intermolecular interactions, see: Takahashi et al. (2001[Takahashi, O., Kohno, Y., Iwasaki, S., Saito, K., Iwaoka, M., Tomada, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2001). Bull. Chem. Soc. Jpn, 74, 2421-2430.]). For ring-puckering calculations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14O3

  • Mr = 254.27

  • Monoclinic, P 21 /n

  • a = 5.2570 (2) Å

  • b = 17.0254 (7) Å

  • c = 14.6879 (5) Å

  • [beta] = 97.806 (2)°

  • V = 1302.42 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEX2 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.991

  • 12297 measured reflections

  • 2288 independent reflections

  • 1523 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.110

  • S = 1.11

  • 2288 reflections

  • 187 parameters

  • 5 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 1.94 2.752 (2) 173
C8-H8...O1ii 0.98 2.39 3.166 (4) 136
C16-H16...Cg1iii 0.93 3.14 4.022 (3) 159
Symmetry codes: (i) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2259 ).


Acknowledgements

SS and CRG thank the Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology (IIT), Chennai, for the data collection, and the Rashtriya Sikshana Samithi Trust (RSST), Sri Shivananda Memorial Rashtriya Vidyalaya (SSMRV) Degree College, for providing research facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Etter, M. C., Urbanczyk-Lipkowska, Z., Baer, S. & Barbara, P. F. (1986). J. Mol. Struct. 144, 155-167.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Klymchenko, A. S., Pivovarenko, V. G. & Demchenko, A. P. (2003). Spectrochim. Acta Part A, 59, 787-792.
Sengupta, P. K. & Kasha, M. (1979). Chem. Phys. Lett. 68, 382-385.  [CrossRef] [ChemPort] [Web of Science]
Shalini, S., Girija, C. R., Simon, L., Srinivasan, K. K., Venkatesha, T. V. & Jotani, M. M. (2013). Acta Cryst. E69, o241.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Takahashi, O., Kohno, Y., Iwasaki, S., Saito, K., Iwaoka, M., Tomada, S., Umezawa, Y., Tsuboyama, S. & Nishio, M. (2001). Bull. Chem. Soc. Jpn, 74, 2421-2430.  [Web of Science] [CrossRef] [ChemPort]
Waller, M. P., Hibbs, D. E., Overgaard, J., Hanrahan, J. R. & Hambley, T. W. (2003). Acta Cryst. E59, o767-o768.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Wera, M., Pivovarenko, V. G. & Blazejowski, J. (2011). Acta Cryst. E67, o264-o265.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1011-o1012   [ doi:10.1107/S1600536813014645 ]

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