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Volume 69 
Part 10 
Page o1516  
October 2013  

Received 19 July 2013
Accepted 2 September 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.181
Data-to-parameter ratio = 13.5
Details
Open access

Dimethyl 3,3'-(phenylmethylene)bis(1H-indole-2-carboxylate)

aChemical Engineering Department, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
Correspondence e-mail: njutshs@126.com

In the title compound, C27H22N2O4, the two indole ring systems are approximately perpendicular to each other, with a dihedral angle of 84.5 (5)° between their planes; the benzene ring is twisted with respect to the two indole ring systems at angles of 78.5 (5) and 86.5 (3)°. In the crystal, molecules are linked by N-H...O hydrogen bonds, weak C-H...O and C-H...N hydrogen bonds, and C-H...[pi] interactions into a three-dimensional supramolecular architecture.

Related literature

For applications of indole derivatives, see: Poter et al. (1977[Poter, J. K., Bacon, C. W., Robins, J. D., Himmelsbach, D. S. & Higman, H. C. (1977). J. Agric. Food Chem. 25, 88-93.]); Sundberg (1996[Sundberg, R. J. (1996). The Chemistry of Indoles, p. 113. New York: Academic Press.]); Chang et al. (1999[Chang, Y.-C., Riby, J., Grace, H. F., Peng, G.-F. & Bieldanes, L. F. (1999). Biochem. Pharmacol. 58, 825-834.]); Ge et al. (1999[Ge, X., Fares, F. A. & Fares, S. Y. (1999). Anticancer Res. 19, 3199-3203.]); Ni (2008[Ni, Y.-C. (2008). Curr. Med. Imaging Rev. 4, 96-112.]); Sun et al. (2012[Sun, H.-S., Li, Y.-L., Xu, N., Xu, H. & Zhang, J.-D. (2012). Acta Cryst. E68, o2764.]).

[Scheme 1]

Experimental

Crystal data
  • C27H22N2O4

  • Mr = 438.47

  • Monoclinic, P 21 /c

  • a = 13.604 (3) Å

  • b = 15.560 (3) Å

  • c = 11.274 (2) Å

  • [beta] = 112.66 (3)°

  • V = 2202.2 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonis CAD-4 diffractometer

  • 4196 measured reflections

  • 4021 independent reflections

  • 2322 reflections with I > 2[sigma](I)

  • Rint = 0.028

  • 3 standard reflections every 200 reflections intensity decay: 1%

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

  • wR(F2) = 0.181

  • S = 1.00

  • 4021 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the N1-pyrrole and C15-benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O2i 0.86 2.02 2.870 (4) 169
C11-H11A...O3ii 0.96 2.60 3.221 (4) 123
C11-H11B...N1iii 0.96 2.61 3.443 (5) 145
C11-H11C...O4i 0.96 2.53 3.333 (5) 142
C5-H5A...Cg4iv 0.93 2.76 3.659 (4) 164
C11-H11B...Cg1iii 0.96 2.55 3.366 (4) 143
C21-H21B...Cg4i 0.96 2.73 3.516 (5) 139
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y, -z+2; (iv) -x, -y, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5723 ).


Acknowledgements

The work was supported by the research fund of Nanjing College of Chemical Technology (grant No. NHKY-2013-02).

References

Chang, Y.-C., Riby, J., Grace, H. F., Peng, G.-F. & Bieldanes, L. F. (1999). Biochem. Pharmacol. 58, 825-834.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Ge, X., Fares, F. A. & Fares, S. Y. (1999). Anticancer Res. 19, 3199-3203.  [PubMed] [ChemPort]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Ni, Y.-C. (2008). Curr. Med. Imaging Rev. 4, 96-112.  [CrossRef] [ChemPort]
Poter, J. K., Bacon, C. W., Robins, J. D., Himmelsbach, D. S. & Higman, H. C. (1977). J. Agric. Food Chem. 25, 88-93.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sun, H.-S., Li, Y.-L., Xu, N., Xu, H. & Zhang, J.-D. (2012). Acta Cryst. E68, o2764.  [CSD] [CrossRef] [IUCr Journals]
Sundberg, R. J. (1996). The Chemistry of Indoles, p. 113. New York: Academic Press.


Acta Cryst (2013). E69, o1516  [ doi:10.1107/S1600536813024471 ]

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