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Volume 69 
Part 8 
Pages o1306-o1307  
August 2013  

Received 10 June 2013
Accepted 9 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.070
wR = 0.145
Data-to-parameter ratio = 12.8
Details
Open access

2-(Diphenylmethylidene)-2,3-dihydro-1H-inden-1-one

aDrug Discovery Group, School of Pharmacy and Pharmaceutical Sciences, Trinity College Dublin, Dublin 2, Ireland, and bSchool of Chemistry, Trinity College Dublin, Dublin 2, Ireland
Correspondence e-mail: hsheridn@tcd.ie

In the title molecule, C22H16O, the indanone ring system is approximately planar with a dihedral angle between the fused rings of 5.13 (14)°. Two benzene rings are linked together at one side of a double bond, sitting on either side of the indanone ring system and making dihedral angles of 70.30 (12) and 44.74 (13)° with it. In the crystal, hydrogen bonding is not present, but weak C-H...[pi] or [pi]-[pi] interactions occur and molecules form a sheet-like structure in the bc plane.

Related literature

For background to the indanone pharmacophore, its use as an organic intermediate and its biological activity, see: Buckle et al. (1973[Buckle, D., Morgan, N., Ross, J., Smith, H. & Spicer, B. (1973). J. Med. Chem. 16, 1334-1339.]); Sheridan et al. (1990[Sheridan, H., Lemon, S., Frankish, N., McCardle, P., Higgins, T., James, J. & Bhandari, P. (1990). Eur. J. Med. Chem. 25, 603-608.], 1999a[Sheridan, H., Frankish, N. & Farrell, R. (1999a). Eur. J. Med. Chem. 34, 953-966.],b[Sheridan, H., Frankish, N. & Farrell, R. (1999b). Planta Med. 65, 271-272.], 2008[Sheridan, H., Butterly, S., Walsh, J. & Frankish, N. (2008). Bioorg. Med. Chem. 16, 248-54.], 2009a[Sheridan, H., Walsh, J., Jordan, M., Cogan, C. & Frankish, N. (2009a). Eur. J. Med. Chem. 44, 5018-5022.],b[Sheridan, H., Walsh, J., Cogan, C., Jordan, M., McCabe, T., Passante, E. & Frankish, N. (2009b). Bioorg. Med. Chem. Lett. 19, 5927-5930.]); Vacca et al. (1994[Vacca, J., Dorsey, B., Schleif, W., Levin, R., McDaniel, S., Darke, P., Zugay, J., Quinterno, J., Blahy, O. & Roth, E. (1994). Proc. Natl Acad. Sci. USA, 91, 4096-4100.]); Schumann et al. (2001[Schumann, H., Stenzel, O., Girgsdies, F. & Halterman, R. L. (2001). Organometallics, 20, 1743-1751.]); Herzog et al. (2002[Herzog, M. N., Chien, J. C. W. & Rausch, M. D. (2002). J. Organomet. Chem. 654, 29-35.]); Frankish et al. (2004[Frankish, N., Farrell, R. & Sheridan, H. (2004). J. Pharm. Pharmacol. 56, 1423-1427.]); Frankish & Sheridan (2012[Frankish, N. & Sheridan, H. (2012). J. Med. Chem. 55, 5497-5505.]); Dinges et al. (2006[Dinges, J., Akritopoulou-Zanze, I., Arnold, L. D., Barlozzari, T., Bousquet, P. F., Cunha, G. A., Ericsson, A. M., Iwasaki, N., Michaelides, M. R., Ogawa, N., Phelan, K. M., Rafferty, P., Sowin, T. J., Stewart, K. D., Tokuyama, R., Xia, Z. & Zhang, H. Q. (2006). Bioorg. Med. Chem. Lett. 16, 4371-4375.]); Kou et al. (2012[Kou, X., Shen, K., An, Y., Qi, S., Dai, W.-X. & Yin, Z. (2012). Phytother. Res. 26, 988-994.]); Ito et al. (2004[Ito, T., Tanaka, T., Iinuma, M., Nakaya, K., Takahashi, Y., Sawa, R., Murata, J. & Darnaedi, D. (2004). J. Nat. Prod. 67, 932-937.]); Jaki et al. (1999[Jaki, B., Orjala, J., Bürgi, H. R. & Sticher, O. (1999). Pharma. Biol. 37, 138-143.]); Chanda et al. (2012[Chanda, D., Bhushan, S., Guru, S. K., Shanker, K., Wani, Z. A., Rah, B. A., Luqman, S., Mondhe, D. M., Pal, A. & Negi, A. S. (2012). Eur. J. Pharm. Sci. 47, 988-995.]); Chen et al. (2008[Chen, Y. H., Chang, F. R., Lu, M. C., Hsieh, P. W., Wu, M. J., Du, Y. C. & Wu, Y. C. (2008). Molecules, 13, 255-266.]); Rukachaisirikul et al. (2013[Rukachaisirikul, V., Buadam, S., Sukpondma, Y., Phongpaichit, S., Sakayaroj, J. & Hutadilok-Towatana, N. (2013). Phytochem. Lett. 6, 135-138.]); Farrell et al. (1996[Farrell, R., Kelleher, F. & Sheridan, H. (1996). J. Nat. Prod. 59, 446-447.]); Borbone et al. (2011[Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290-295.]); Fu & Wang (2008[Fu, T. L. & Wang, I. J. (2008). Dyes Pigm. 76, 590-595.]). For bond lengths and angles in related compounds, see: Ali et al. (2010a[Ali, M. A., Ismail, R., Tan, S. C., Quah, C. K. & Fun, H.-K. (2010a). Acta Cryst. E66, o2875.],b[Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010b). Acta Cryst. E66, o2864.], 2011[Ali, M. A., Ismail, R., Choon, T. S., Loh, W.-S. & Fun, H.-K. (2011). Acta Cryst. E67, o2306-o2307.]); Chen et al. (2011a[Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.] 2011b[Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.]); Li et al. (2012[Li, H., Fronczek, F. R. & Watkins, S. F. (2012). Acta Cryst. E68, o2756.]); Lin et al. (2012[Lin, H.-Y., Chang, C.-W., Tsai, H.-Y., Luo, M.-H. & Chen, K.-Y. (2012). Acta Cryst. E68, o3075-o3076.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16O

  • Mr = 296.35

  • Monoclinic, P 21 /c

  • a = 9.1634 (18) Å

  • b = 17.570 (3) Å

  • c = 10.717 (4) Å

  • [beta] = 117.89 (2)°

  • V = 1525.0 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 150 K

  • 0.50 × 0.20 × 0.20 mm

Data collection
  • Rigaku Saturn 724 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2006[Rigaku (2006). CrystalClear. Rigaku Corporation. Tokyo. Japan.]) Tmin = 0.763, Tmax = 1.000

  • 11746 measured reflections

  • 2680 independent reflections

  • 2587 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.145

  • S = 1.25

  • 2680 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the C14-C16/C21/C22, C1-C6 and C16-C21 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C1-H1...Cg1i 0.93 2.91 3.763 (3) 153
C11-H11...Cg2ii 0.93 2.99 3.712 (3) 136
C15-H15B...Cg4iii 0.97 2.92 3.640 (3) 132
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2006[Rigaku (2006). CrystalClear. Rigaku Corporation. Tokyo. Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97 and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2117 ).


Acknowledgements

We wish to thank Trinity College Dublin for financial support, Trinity College Postgraduate Research Studentships.

References

Ali, M. A., Ismail, R., Choon, T. S., Loh, W.-S. & Fun, H.-K. (2011). Acta Cryst. E67, o2306-o2307.  [CrossRef] [ChemPort] [IUCr Journals]
Ali, M. A., Ismail, R., Tan, S. C., Quah, C. K. & Fun, H.-K. (2010a). Acta Cryst. E66, o2875.  [CrossRef] [IUCr Journals]
Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010b). Acta Cryst. E66, o2864.  [CrossRef] [IUCr Journals]
Borbone, F., Carella, A., Ricciotti, L., Tuzi, A., Roviello, A. & Barsella, A. (2011). Dyes Pigm. 88, 290-295.  [CSD] [CrossRef] [ChemPort]
Buckle, D., Morgan, N., Ross, J., Smith, H. & Spicer, B. (1973). J. Med. Chem. 16, 1334-1339.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Chanda, D., Bhushan, S., Guru, S. K., Shanker, K., Wani, Z. A., Rah, B. A., Luqman, S., Mondhe, D. M., Pal, A. & Negi, A. S. (2012). Eur. J. Pharm. Sci. 47, 988-995.  [CrossRef] [ChemPort] [PubMed]
Chen, Y. H., Chang, F. R., Lu, M. C., Hsieh, P. W., Wu, M. J., Du, Y. C. & Wu, Y. C. (2008). Molecules, 13, 255-266.  [CrossRef] [PubMed] [ChemPort]
Chen, K.-Y., Fang, T.-C. & Chang, M.-J. (2011a). Acta Cryst. E67, o992.  [CSD] [CrossRef] [IUCr Journals]
Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011b). Acta Cryst. E67, o927.  [CSD] [CrossRef] [IUCr Journals]
Dinges, J., Akritopoulou-Zanze, I., Arnold, L. D., Barlozzari, T., Bousquet, P. F., Cunha, G. A., Ericsson, A. M., Iwasaki, N., Michaelides, M. R., Ogawa, N., Phelan, K. M., Rafferty, P., Sowin, T. J., Stewart, K. D., Tokuyama, R., Xia, Z. & Zhang, H. Q. (2006). Bioorg. Med. Chem. Lett. 16, 4371-4375.  [CrossRef] [PubMed] [ChemPort]
Farrell, R., Kelleher, F. & Sheridan, H. (1996). J. Nat. Prod. 59, 446-447.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Frankish, N., Farrell, R. & Sheridan, H. (2004). J. Pharm. Pharmacol. 56, 1423-1427.  [CrossRef] [PubMed] [ChemPort]
Frankish, N. & Sheridan, H. (2012). J. Med. Chem. 55, 5497-5505.  [CrossRef] [ChemPort] [PubMed]
Fu, T. L. & Wang, I. J. (2008). Dyes Pigm. 76, 590-595.  [CrossRef] [ChemPort]
Herzog, M. N., Chien, J. C. W. & Rausch, M. D. (2002). J. Organomet. Chem. 654, 29-35.  [CrossRef] [ChemPort]
Ito, T., Tanaka, T., Iinuma, M., Nakaya, K., Takahashi, Y., Sawa, R., Murata, J. & Darnaedi, D. (2004). J. Nat. Prod. 67, 932-937.  [CrossRef] [PubMed] [ChemPort]
Jaki, B., Orjala, J., Bürgi, H. R. & Sticher, O. (1999). Pharma. Biol. 37, 138-143.  [CrossRef]
Kou, X., Shen, K., An, Y., Qi, S., Dai, W.-X. & Yin, Z. (2012). Phytother. Res. 26, 988-994.  [CrossRef] [ChemPort] [PubMed]
Li, H., Fronczek, F. R. & Watkins, S. F. (2012). Acta Cryst. E68, o2756.  [CrossRef] [IUCr Journals]
Lin, H.-Y., Chang, C.-W., Tsai, H.-Y., Luo, M.-H. & Chen, K.-Y. (2012). Acta Cryst. E68, o3075-o3076.  [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Rigaku (2006). CrystalClear. Rigaku Corporation. Tokyo. Japan.
Rukachaisirikul, V., Buadam, S., Sukpondma, Y., Phongpaichit, S., Sakayaroj, J. & Hutadilok-Towatana, N. (2013). Phytochem. Lett. 6, 135-138.  [CrossRef] [ChemPort]
Schumann, H., Stenzel, O., Girgsdies, F. & Halterman, R. L. (2001). Organometallics, 20, 1743-1751.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheridan, H., Butterly, S., Walsh, J. & Frankish, N. (2008). Bioorg. Med. Chem. 16, 248-54.  [CrossRef] [PubMed] [ChemPort]
Sheridan, H., Frankish, N. & Farrell, R. (1999a). Eur. J. Med. Chem. 34, 953-966.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheridan, H., Frankish, N. & Farrell, R. (1999b). Planta Med. 65, 271-272.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheridan, H., Lemon, S., Frankish, N., McCardle, P., Higgins, T., James, J. & Bhandari, P. (1990). Eur. J. Med. Chem. 25, 603-608.  [CrossRef] [ChemPort] [Web of Science]
Sheridan, H., Walsh, J., Cogan, C., Jordan, M., McCabe, T., Passante, E. & Frankish, N. (2009b). Bioorg. Med. Chem. Lett. 19, 5927-5930.  [CrossRef] [PubMed] [ChemPort]
Sheridan, H., Walsh, J., Jordan, M., Cogan, C. & Frankish, N. (2009a). Eur. J. Med. Chem. 44, 5018-5022.  [CrossRef] [PubMed] [ChemPort]
Vacca, J., Dorsey, B., Schleif, W., Levin, R., McDaniel, S., Darke, P., Zugay, J., Quinterno, J., Blahy, O. & Roth, E. (1994). Proc. Natl Acad. Sci. USA, 91, 4096-4100.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1306-o1307   [ doi:10.1107/S1600536813018990 ]

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