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

Kaur, M.; Butcher, R.J.; Akkurt, M.; Yathirajan, H.S.; Nagaraj, B.

doi:10.1107/S1600536812050088

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 (C-C) = 0.002 Å
R = 0.034
wR = 0.091
Data-to-parameter ratio = 13.1
Details

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

Manpreet Kaur,^a Ray J. Butcher,^b Mehmet Akkurt,^c H. S. Yathirajan ^a ^* and B. Nagaraj ^d

^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-HN hydrogen bonds, forming zigzag C(7) chains of alternating A and B molecules running parallel to [100]. The structure also features weak C-HO and C-H [pi] interactions.

Related literature

For a historical perspective on the applications of anthrone, see: Trevelyan (1952). For related structures see: Abboud et al. (1991); Fun et al. (2010, 2011); Siddaraju et al. (2011); Yannoni & Silverman (1966).

Experimental

Crystal data

C₂₁H₂₇NO
M_r = 309.44
Monoclinic, P 2₁
a = 11.79596 (9) Å
b = 9.17559 (7) Å
c = 16.75788 (13) Å
= 92.2372 (7)°
V = 1812.41 (2) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.838, T_max = 1.000
12252 measured reflections
5579 independent reflections
5539 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.091
S = 1.06
5579 reflections
425 parameters
1 restraint
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.23 e Å^-3
Absolute structure: Flack (1983), 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-HA	D-H	HA	DA	D-HA
O1A-H1AN1B	0.84	2.03	2.8659 (16)	170
O1B-H1BN1Aⁱ	0.84	2.03	2.8428 (16)	161
C17A-H17BO1Bⁱⁱ	0.99	2.56	3.3166 (17)	133
C20B-H20FCg1	0.98	2.82	3.5941 (17)	136
C21A-H21ACg2ⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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

organic compounds