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Volume 69 
Part 2 
Page o175  
February 2013  

Received 29 November 2012
Accepted 7 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.091
Data-to-parameter ratio = 13.1
Details
Open access

9-[3-(Dimethylamino)propyl]-10,10-dimethyl-9,10-dihydroanthracen-9-ol

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dDepartment of Biotechnology, Shridevi Institute of Engineering & Technology, Tumkur 572 106, India
Correspondence e-mail: yathirajan@hotmail.com_and_akkurt@erciyes.edu.tr

The asymmetric unit of the title compound, C21H27NO, contains two molecules (A and B). In molecule A, the central ring of the anthrone unit adopts a shallow boat conformation and the dihedral angle between the benzene rings is 18.96 (7)°. In molecule B, the central ring is close to being planar (r.m.s. deviation = 0.078 Å) and the dihedral angle between the aromatic rings is 7.82 (7)°. In the crystal, molecules are linked by O-H...N hydrogen bonds, forming zigzag C(7) chains of alternating A and B molecules running parallel to [100]. The structure also features weak C-H...O and C-H...[pi] interactions.

Related literature

For a historical perspective on the applications of anthrone, see: Trevelyan (1952[Trevelyan, W. E. (1952). Nature (London), 170, 626-627.]). For related structures see: Abboud et al. (1991[Abboud, K. A., Simonsen, S. H., Prasad, R. S. & Roberts, R. M. (1991). Acta Cryst. C47, 880-882.]); Fun et al. (2010[Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Siddegowda, M. S. (2010). Acta Cryst. E66, o808-o809.], 2011[Fun, H.-K., Hemamalini, M., Siddegowda, M. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o1725.]); Siddaraju et al. (2011[Siddaraju, B. P., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Raju, C. R. (2011). Acta Cryst. E67, o2397.]); Yannoni & Silverman (1966[Yannoni, N. F. & Silverman, J. (1966). Acta Cryst. 21, 390-396.]).

[Scheme 1]

Experimental

Crystal data
  • C21H27NO

  • Mr = 309.44

  • Monoclinic, P 21

  • a = 11.79596 (9) Å

  • b = 9.17559 (7) Å

  • c = 16.75788 (13) Å

  • [beta] = 92.2372 (7)°

  • V = 1812.41 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.53 mm-1

  • T = 123 K

  • 0.41 × 0.34 × 0.27 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemin) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.838, Tmax = 1.000

  • 12252 measured reflections

  • 5579 independent reflections

  • 5539 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.091

  • S = 1.06

  • 5579 reflections

  • 425 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1564 Freidel pairs

  • Flack parameter: 0.08 (17)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11A-C16A and C2B-C7B benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
O1A-H1A...N1B 0.84 2.03 2.8659 (16) 170
O1B-H1B...N1Ai 0.84 2.03 2.8428 (16) 161
C17A-H17B...O1Bii 0.99 2.56 3.3166 (17) 133
C20B-H20F...Cg1 0.98 2.82 3.5941 (17) 136
C21A-H21A...Cg2ii 0.98 2.97 3.8017 (18) 143
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7006 ).


Acknowledgements

MK thanks the University of Mysore for research facilities. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Abboud, K. A., Simonsen, S. H., Prasad, R. S. & Roberts, R. M. (1991). Acta Cryst. C47, 880-882.  [CrossRef] [details]
Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Siddegowda, M. S. (2010). Acta Cryst. E66, o808-o809.  [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Siddegowda, M. S., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o1725.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siddaraju, B. P., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Raju, C. R. (2011). Acta Cryst. E67, o2397.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Trevelyan, W. E. (1952). Nature (London), 170, 626-627.  [CrossRef] [PubMed] [ChemPort] [ISI]
Yannoni, N. F. & Silverman, J. (1966). Acta Cryst. 21, 390-396.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o175  [ doi:10.1107/S1600536812050088 ]

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