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Volume 69 
Part 11 
Pages o1626-o1627  
November 2013  

Received 3 September 2013
Accepted 3 October 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.062
wR = 0.191
Data-to-parameter ratio = 15.0
Details
Open access

2,2'-Bis{8-[(benzyl­amino)­methyl­idene]-1,6-dihy­droxy-5-isopropyl-3-methyl­naphthalen-7(8H)-one}

aNational University of Uzbekistan, Faculty of Chemistry, Vuzgorodok, Tashkent 100095, Uzbekistan, and bInstitute of Bioorganic Chemistry, Mirzo-Ulugbek St. 83, Tashkent 100125, Uzbekistan
Correspondence e-mail: h.shuxrat81@mail.ru

The asymmetric unit of the title compound, C44H44N2O6, contains two independent mol­ecules with similar conformations. The di­hydro­naphthalene ring systems are approximately planar [maximum deviations = 0.036 (2), 0.128 (2), 0.0.24 (2) and 0.075 (2) Å]. The dihedral angle between two di­hydro­naphthalene ring systems is 83.37 (4)° in one mol­ecule and 88.99 (4)° in the other. The carbonyl O atom is linked with the adjacent hy­droxy and imino groups via intra­molecular O-H...O and N-H...O hydrogen bonds. In the crystal, mol­ecules are linked through O-H...O hydrogen bonds into layers parallel to (001), and adjacent layers are further stacked by [pi]-[pi] inter­actions between di­hydro­naphthalene and phenyl rings into a three-dimensional supra­molecular architecture. In the crystal, one of the isopropyl groups is disordered over two positions with an occupancy ratio of 0.684 (8):0.316 (8).

Related literature

For details of extraction and synthesis of gossypol and its derivatives, see: Kenar (2006[Kenar, J. A. (2006). J. Am. Oil Chem. Soc. 83, 269-303.]). For synthesis and biological activities, see: Polsky et al. (1989[Polsky, B., Segal, S. J., Baron, P. A., Gold, J. W., Ueno, H. & Armstrong, D. (1989). Contraception, 39, 579-587.]); Radloff et al. (1985[Radloff, R. I., Deck, L. M., Royer, R. E. & Vander Jagt, D. L. (1985). Pharmacol. Res. Commun. 18, 1063-1073.]). For formation of crystalline forms of inclusion compounds, see: Ibragimov & Talipov (1999[Ibragimov, B. T. & Talipov, S. A. (1999). J. Struct. Chem. 40, 686-704.], 2004[Ibragimov, B. T. & Talipov, S. A. (2004). Gossypol, in Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 606-614. New York: Dekker.]).

[Scheme 1]

Experimental

Crystal data
  • C44H44N2O6

  • Mr = 696.81

  • Monoclinic, P 21 /c

  • a = 9.8118 (8) Å

  • b = 29.014 (2) Å

  • c = 25.5854 (17) Å

  • [beta] = 90.196 (6)°

  • V = 7283.6 (9) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.68 mm-1

  • T = 293 K

  • 0.6 × 0.3 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.66, Tmax = 0.88

  • 54670 measured reflections

  • 15043 independent reflections

  • 7763 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.191

  • S = 0.94

  • 15043 reflections

  • 1001 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AN...O3A 0.86 1.79 2.494 (3) 138
N1B-H1BN...O3B 0.86 1.85 2.531 (3) 135
N2A-H2AN...O7A 0.86 1.93 2.584 (3) 132
N2B-H2BN...O7B 0.86 1.89 2.561 (3) 134
O1A-H1A...O7Bi 0.65 (2) 2.24 (3) 2.778 (3) 141 (3)
O1B-H1B...O7Aii 0.77 (3) 2.33 (3) 2.846 (2) 125 (3)
O4A-H4AB...O3A 0.74 (3) 2.05 (3) 2.588 (3) 130 (3)
O4B-H4BC...O3B 0.83 (4) 1.98 (4) 2.568 (4) 126 (4)
O5A-H5A...O3B 0.76 (3) 2.10 (3) 2.714 (3) 138 (3)
O5B-H5B...O3A 0.81 (3) 1.98 (3) 2.645 (3) 139 (3)
O8A-H8A...O1Biii 0.92 (5) 2.45 (5) 3.290 (3) 151 (4)
O8A-H8A...O7A 0.92 (5) 1.95 (5) 2.592 (3) 126 (4)
O8B-H8B...O1Aiv 0.86 (5) 2.40 (5) 3.183 (3) 151 (4)
O8B-H8B...O7B 0.86 (5) 1.93 (5) 2.577 (3) 130 (4)
Symmetry codes: (i) [-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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: XP (Bruker, 1998[Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5738 ).


Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study F7-T048

References

Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.
Ibragimov, B. T. & Talipov, S. A. (1999). J. Struct. Chem. 40, 686-704.  [Web of Science] [CrossRef] [ChemPort]
Ibragimov, B. T. & Talipov, S. A. (2004). Gossypol, in Encyclopedia of Supramolecular Chemistry, edited by J. L. Atwood & J. W. Steed, pp. 606-614. New York: Dekker.
Kenar, J. A. (2006). J. Am. Oil Chem. Soc. 83, 269-303.  [CrossRef] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Polsky, B., Segal, S. J., Baron, P. A., Gold, J. W., Ueno, H. & Armstrong, D. (1989). Contraception, 39, 579-587.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Radloff, R. I., Deck, L. M., Royer, R. E. & Vander Jagt, D. L. (1985). Pharmacol. Res. Commun. 18, 1063-1073.  [CrossRef] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1626-o1627   [ doi:10.1107/S1600536813027281 ]

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