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Volume 69 
Part 10 
Pages o1547-o1548  
October 2013  

Received 29 July 2013
Accepted 9 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.076
Data-to-parameter ratio = 12.7
Details
Open access

2-(2-Methylbenzoyl)benzoic acid: catemeric hydrogen bonding in a [gamma]-keto acid1

aCarl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102 , USA, and bDepartment of Chemistry, Touro College - Lander College for Men, New York, NY , USA
Correspondence e-mail: rogerlal@andromeda.rutgers.edu

The crystal structure of the title compound, C15H12O3, displays catemeric aggregation involving O-H...O hydrogen bonds progressing from the carboxyl group of one molecule to the ketone O atom of another glide-related neighbor. The molecule is twisted, with the toluene 80.61 (3)° out of plane with respect to the phenyl group of the benzoic acid. The acid group makes a dihedral angle of 13.79 (14)° with the attached phenyl ring. The molecules are achiral, but the space group glide planes create alternating conformational chirality in the chain units. The four hydrogen-bonding chains progress along [001] in an A-A-B-B pattern (right-to-left versus left-to-right), and are related to each other by the center of symmetry at (0.5, 0.5, 0.5) in the chosen cell. There is one close contact (2.54 Å) between a phenyl H atom and the acid carbonyl from a symmetry-related molecule.

Related literature

For a discussion of highly ordered carboxyl bond distances and angles, see: Borthwick (1980[Borthwick, P. W. (1980). Acta Cryst. B36, 628-632.]). For close contact information, see: Steiner (1997[Steiner, T. (1997). Chem. Commun. pp. 727-734.]). For related structures, see: Abell et al. (1991[Abell, A. D., Trent, J. & Robinson, W. P. (1991). J. Chem. Soc. Chem. Commun. pp. 362-363.]); Barcon et al. (1998[Barcon, A., Brunskill, A. P. J., Lalancette, R. A. & Thompson, H. W. (1998). Acta Cryst. C54, 1282-1285.], 2002[Barcon, A., Brunskill, A. P. J., Lalancette, R. A. & Thompson, H. W. (2002). Acta Cryst. C58, o154-o156.]); Degen & Bolte (1999[Degen, A. & Bolte, M. (1999). Acta Cryst. C55, 1306-1308.]); Hickmott et al. (1985[Hickmott, P. W., Ahmed, M. G., Ahmed, S. A., Wood, S. & Kapon, M. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 2559-2571.]); Kashyap et al. (1995[Kashyap, R. P., Deshpande, M. N., Rajapaksa, D., Marchand, A. P. & Watson, W. H. (1995). J. Chem. Crystallogr. 25, 573-578.]); Song et al. (2008[Song, G.-L., Deng, S.-P., Liu, S. & Zhu, H.-J. (2008). Acta Cryst. E64, o894.]); Thompson et al. (1998[Thompson, H. W., Brunskill, A. P. J. & Lalancette, R. A. (1998). Acta Cryst. C54, 829-831.]); Watson et al. (1990[Watson, W. H., Nagl, A., Kashyap, R. P., Marchand, A. P. & Vidyasagar, V. (1990). Acta Cryst. C46, 1265-1268.]). For preparation of the title compound, see: Newman & McCleary (1941[Newman, M. S. & McCleary, C. D. (1941). J. Am. Chem. Soc. 63, 1537-1541.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12O3

  • Mr = 240.25

  • Orthorhombic, P b c a

  • a = 10.7450 (2) Å

  • b = 10.1737 (2) Å

  • c = 21.6588 (4) Å

  • V = 2367.66 (8) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.77 mm-1

  • T = 100 K

  • 0.45 × 0.26 × 0.20 mm

Data collection
  • Bruker SMART CCD APEXII area-detector diffractometer

  • Absorption correction: numerical (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.724, Tmax = 0.862

  • 20799 measured reflections

  • 2143 independent reflections

  • 2075 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.076

  • S = 1.07

  • 2143 reflections

  • 169 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O1ii 0.932 (18) 1.714 (18) 2.6477 (11) 172.3 (16)
Symmetry code: (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2513 ).


Acknowledgements

The authors acknowledge support by NSF-CRIF grant No. 0443538.

References

Abell, A. D., Trent, J. & Robinson, W. P. (1991). J. Chem. Soc. Chem. Commun. pp. 362-363.  [CrossRef] [Web of Science]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Barcon, A., Brunskill, A. P. J., Lalancette, R. A. & Thompson, H. W. (1998). Acta Cryst. C54, 1282-1285.  [CSD] [CrossRef] [IUCr Journals]
Barcon, A., Brunskill, A. P. J., Lalancette, R. A. & Thompson, H. W. (2002). Acta Cryst. C58, o154-o156.  [CSD] [CrossRef] [IUCr Journals]
Borthwick, P. W. (1980). Acta Cryst. B36, 628-632.  [CrossRef] [IUCr Journals]
Bruker (2005). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Degen, A. & Bolte, M. (1999). Acta Cryst. C55, 1306-1308.  [CSD] [CrossRef] [IUCr Journals]
Hickmott, P. W., Ahmed, M. G., Ahmed, S. A., Wood, S. & Kapon, M. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 2559-2571.  [CSD] [CrossRef]
Kashyap, R. P., Deshpande, M. N., Rajapaksa, D., Marchand, A. P. & Watson, W. H. (1995). J. Chem. Crystallogr. 25, 573-578.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Newman, M. S. & McCleary, C. D. (1941). J. Am. Chem. Soc. 63, 1537-1541.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Song, G.-L., Deng, S.-P., Liu, S. & Zhu, H.-J. (2008). Acta Cryst. E64, o894.  [CSD] [CrossRef] [IUCr Journals]
Steiner, T. (1997). Chem. Commun. pp. 727-734.  [CrossRef]
Thompson, H. W., Brunskill, A. P. J. & Lalancette, R. A. (1998). Acta Cryst. C54, 829-831.  [CSD] [CrossRef] [IUCr Journals]
Watson, W. H., Nagl, A., Kashyap, R. P., Marchand, A. P. & Vidyasagar, V. (1990). Acta Cryst. C46, 1265-1268.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1547-o1548   [ doi:10.1107/S1600536813025099 ]

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