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

Manpreet Kaur; Ray J Butcher; Mehmet Akkurt; H S Yathirajan; B Nagaraj

doi:10.1107/S1600536812050088

. 2013 Jan 4;69(Pt 2):o175. doi: 10.1107/S1600536812050088

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,^*, B Nagaraj ^d

PMCID: PMC3569237 PMID: 23424460

Abstract

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⋯π 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,
a = 11.79596 (9) Å
b = 9.17559 (7) Å
c = 16.75788 (13) Å
β = 92.2372 (7)°
V = 1812.41 (2) Å³
Z = 4
Cu Kα radiation
μ = 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 > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.091
S = 1.06
5579 reflections
425 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 1564 Freidel pairs
Flack parameter: 0.08 (17)

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 Material

Click here for additional data file.^{(46.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050088/hb7006sup1.cif

e-69-0o175-sup1.cif^{(46.1KB, cif)}

Click here for additional data file.^{(273.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050088/hb7006Isup2.hkl

e-69-0o175-Isup2.hkl^{(273.1KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050088/hb7006Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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⋯N1A ⁱ	0.84	2.03	2.8428 (16)	161
C17A—H17B⋯O1B ⁱⁱ	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

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

Anthracene and its derivatives are long known polycyclic aromatic compounds showing a high potential for use in materials science (e.g. fluorescence probing, photochromic systems, electroluminescence) and several reviews have been published. Anthrone is a tricyclic aromatic hydrocarbon which is used for a popular cellulose assay and in the colorometric determination of carbohydrates (Trevelyan, 1952) and anthracene itself is used in the production of red dye alizarin. The crystal structures of 9,9,10,10-tetrachloro-9,10-dihydroanthracene (Yannoni & Silverman, 1966), cis-9,10-dibenzyl-9,10-dihydroanthracene (Abboud et al., 1991), 9,9-dimethyl-9,10-dihydroanthracene (Siddaraju et al., 2011); 10,10-dimethylanthrone (Fun et al., 2010) and melitracenium chloride (Fun et al., 2011) have been reported.

As part of our studies in this area, this paper reports the crystal structure of the title compound (I).

As shown in Fig. 1, there are two crystallographically independent molecules (A with the suffix A and B with the suffix B) in the asymmetric unit. In molecule A, the cyclohexane ring (C1A/C2A/C7A/C8A/C11A/C16A) adopts a shallow boat conformation, while the anthracene unit (C1B–C8B/C11B–C16B) with the cyclohexane ring in molecule B, is nearly planar, with a maximum deviation of 0.216 (1) Å for C1B. In molecules A and B, the dihedral angles between the terminal benzene rings are 18.96 (7) and 7.82 (7)°, respectively. In both molecules A and B, the values of the bond lengths and angles agree with each other.

The crystal structure is stabilized by O—H···N hydrogen bonds, forming zigzag C(7) chains running parallel to the [100] direction (Table 1, Fig. 2). Further stabilization is provided by C—H···π interactions (Table 1), involving the C11A–C16A (centroid Cg1) and C2B–C7B (centroid Cg2) benzene rings.

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bengaluru, India. Colourless prisms were obtained from toluene solution by slow evaporation (m.p.: 395 – 397 K).