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Volume 69 
Part 9 
Page o1448  
September 2013  

Received 31 July 2013
Accepted 14 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.115
Data-to-parameter ratio = 16.8
Details
Open access

(E)-3-{[([1,1'-Biphenyl]-3-ylmethyl)iminiumyl]methyl}-6,8-dichloro-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 crystal of the title compound, C23H17Cl2NO2, the H atom of the -OH group is transferred to the N atom of the imine, forming a zwitterion. This results in a six-membered intramolecular O...H-N hydrogen-bonded ring, rather than that formed with an O-H...N hydrogen bond. The dihedral angle between the rings of the biphenyl unit is 13.88 (10)°. In the crystal, molecules are linked by N-H...O 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.]); Ishikawa & Motohashi (2013a[Ishikawa, Y. & Motohashi, Y. (2013a). Acta Cryst. E69, o1225.],b[Ishikawa, Y. & Motohashi, Y. (2013b). Acta Cryst. E69, o1226.]).

[Scheme 1]

Experimental

Crystal data
  • C23H17Cl2NO2

  • Mr = 410.30

  • Monoclinic, P 21 /c

  • a = 17.996 (8) Å

  • b = 9.127 (6) Å

  • c = 11.649 (7) Å

  • [beta] = 102.00 (4)°

  • V = 1871.5 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 100 K

  • 0.40 × 0.25 × 0.25 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 5086 measured reflections

  • 4254 independent reflections

  • 3499 reflections with F2 > 2[sigma](F2)

  • Rint = 0.090

  • 3 standard reflections every 150 reflections intensity decay: -0.7%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.115

  • S = 1.01

  • 4254 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.69 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5...O4 0.88 2.20 2.811 (3) 126
N5-H5...O4i 0.88 2.38 3.081 (3) 137
C25-H25A...O4ii 0.99 2.59 3.546 (4) 164
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: HB7114 ).


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] [details]
Ishikawa, Y. & Motohashi, Y. (2013a). Acta Cryst. E69, o1225.  [CrossRef] [details]
Ishikawa, Y. & Motohashi, Y. (2013b). Acta Cryst. E69, o1226.  [CrossRef] [details]
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] [details]
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] [details]
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, o1448  [ doi:10.1107/S160053681302285X ]

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