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Volume 69 
Part 8 
Page o1226  
August 2013  

Received 20 June 2013
Accepted 1 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.083
Data-to-parameter ratio = 16.5
Details
Open access

(E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate

aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

In the title compound, C21H15Cl2NO2, the H atom of the -OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is formation of a six-membered ring via an intramolecular O...H-N, rather than O-H...N, hydrogen bond in the molecule. The dihedral angle between the naphthalene ring system and the benzene ring of the 2H-chromen system is 87.41 (4)°. In the crystal, the molecules are packed through N-H...O, [pi]-[pi] [centroid-centroid distances = 3.744 (3) and 3.780 (3) Å], C-Cl...[pi] [Cl...centroid = 3.261 (3) Å], C-H...[pi] and C-H...O interactions.

Related literature

For the biological propertries of similar structures, see: Khan et al. (2009[Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983-2988.]); Tu et al. (2013[Tu, Q. D., Li, D., Sun, Y., Han, X. Y., Yi, F., Sha, Y., Ren, Y. L., Ding, M. W., Feng, L. L. & Wan, J. (2013). Bioorg. Med. Chem. 21, 2826-2831.]). For related structures, see: Benaouida et al. (2013[Benaouida, M. A., Chetioui, S. & Bouaoud, S. E. (2013). Acta Cryst. E69, o867-o868.]); Malecka & Budzisz (2006[Malecka, M. & Budzisz, E. (2006). Acta Cryst. E62, o5058-o5060.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15Cl2NO2

  • Mr = 384.26

  • Monoclinic, P 21 /c

  • a = 16.286 (7) Å

  • b = 8.910 (6) Å

  • c = 12.008 (9) Å

  • [beta] = 102.65 (4)°

  • V = 1700.2 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.40 mm-1

  • T = 100 K

  • 0.37 × 0.37 × 0.28 mm

Data collection
  • Rigaku AFC7R diffractometer

  • 4657 measured reflections

  • 3875 independent reflections

  • 3367 reflections with F2 > 2.0[sigma](F2)

  • Rint = 0.083

  • 3 standard reflections every 150 reflections intensity decay: -0.4%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.083

  • S = 1.04

  • 3875 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4-C9 ring.

D-H...A D-H H...A D...A D-H...A
N1-H6...O2 0.88 2.18 2.794 (2) 126
N1-H6...O2i 0.88 2.54 3.306 (3) 146
C1-H2A...O2ii 0.99 2.52 3.472 (3) 160
C15-H11...Cg2iii 0.95 2.77 3.682 (3) 160
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y+2, -z+1.

Data collection: WinAFC (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC; data reduction: WinAFC; 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: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2006 ).


Acknowledgements

We acknowledge the University of Shizuoka for supporting this study.

References

Benaouida, M. A., Chetioui, S. & Bouaoud, S. E. (2013). Acta Cryst. E69, o867-o868.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Khan, K. M., Ambreen, N., Hussain, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 2983-2988.  [CrossRef] [PubMed] [ChemPort]
Malecka, M. & Budzisz, E. (2006). Acta Cryst. E62, o5058-o5060.  [CSD] [CrossRef] [IUCr Journals]
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tu, Q. D., Li, D., Sun, Y., Han, X. Y., Yi, F., Sha, Y., Ren, Y. L., Ding, M. W., Feng, L. L. & Wan, J. (2013). Bioorg. Med. Chem. 21, 2826-2831.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1226  [ doi:10.1107/S1600536813018084 ]

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