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Volume 68 
Part 11 
Page o3158  
November 2012  

Received 8 October 2012
Accepted 10 October 2012
Online 20 October 2012

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Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.003 Å
R = 0.056
wR = 0.126
Data-to-parameter ratio = 14.7
Details
Open access

(1E,2E)-1,2-Bis[(1-benzyloxymethyl-1H-indol-3-yl)methylidene]hydrazine

Jacob A. Myers,a Frank R. Fronczeka* and Steven F. Watkinsa

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C34H30N4O2, lies on an inversion center and consists of two 3-substituted-1H-indole units linked by a 1,2-dimethylenehydrazine bridge. It is one of numerous examples in which two aromatic ring systems are joined by this 4-atom bridge. The geometry of the centrosymmetric bridge is: C(arom)-C = 1.444 (3), C=N = 1.284 (3), N-N = 1.414 (4) Å, C(arom)-C=N = 122.6 (2) and C=N-N = 111.9 (2)°. The nine non-H atoms of the indole unit lie in a plane ([delta]r.m.s. = 0.0089 Å) which is twisted 6.0 (2)° with respect to the hydrazine bridge plane. The benzyloxymethyl substituents do not lie in the plane of the rest of the molecule and are in a folded rather than an extended conformation. This is described by the three torsion angles in the middle of the C=N-C-O-CBz group, viz. 98.5 (3), -62.1 (3), and -66.3 (2)°.

Related literature

For the synthesis, see: Shui (1994[Shui, L. (1994). PhD Dissertation, Louisiana State University, Baton Rouge, Louisiana, USA.]). For related structures, see: Burke-Laing & Laing (1976[Burke-Laing, M. & Laing, M. (1976). Acta Cryst. B32, 3216-3224.]); Mom & de With (1978[Mom, V. & de With, G. (1978). Acta Cryst. B34, 2785-2789.]); Biswas et al. (1999[Biswas, K. M., Mallik, H., Saha, A., Halder, S. & McPhail, A. T. (1999). Monatsh. Chem. 130, 1227-1239.]); Rizal et al. (2008[Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o555.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C34H30N4O2

  • Mr = 526.62

  • Monoclinic, P 21 /n

  • a = 12.8518 (10) Å

  • b = 7.9663 (9) Å

  • c = 13.6810 (12) Å

  • [beta] = 103.672 (5)°

  • V = 1361.0 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 90 K

  • 0.18 × 0.10 × 0.05 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.986, Tmax = 0.996

  • 4340 measured reflections

  • 2678 independent reflections

  • 1481 reflections with I > 2[sigma](I)

  • Rint = 0.067
Refinement

  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.126

  • S = 0.99

  • 2678 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SHELXS86 (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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2449 ).

Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents. We thank Dr Lee Shui for kindly providing the sample.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Biswas, K. M., Mallik, H., Saha, A., Halder, S. & McPhail, A. T. (1999). Monatsh. Chem. 130, 1227-1239.  [ChemPort]
Burke-Laing, M. & Laing, M. (1976). Acta Cryst. B32, 3216-3224.  [CrossRef] [details] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Mom, V. & de With, G. (1978). Acta Cryst. B34, 2785-2789.  [CrossRef] [details] [ISI]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o555.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shui, L. (1994). PhD Dissertation, Louisiana State University, Baton Rouge, Louisiana, USA.

Acta Cryst (2012). E68, o3158  [ doi:10.1107/S1600536812042493 ]

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