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Volume 68 
Part 12 
Page o3441  
December 2012  

Received 8 November 2012
Accepted 13 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 14.2
Details
Open access

5-Benzoyl-2-(1H-indol-3-yl)-4-[4-(propan-2-yl)phenyl]-4,5-dihydrofuran-3-carbonitrile

aDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
Correspondence e-mail: mailtorvkk@yahoo.co.in

In the title compound, C29H24N2O2, the hydrofuran ring is twisted with puckering parameters Q = 0.1553 (16) Å and [varphi] = 305.0 (6)°. In the crystal, the graph-set motifs of the interaction pattern are an R22(16) motif involving dimers through N-H...N hydrogen bonds across centres of inversion and a C(6) motif through C-H...O hydrogen-bond between glide-related molecules. Together, these generate [101] ladder-like chains.

Related literature

For related structures, see: Suresh et al. (2012a[Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012a). Acta Cryst. E68, o1576.],b[Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012b). Acta Cryst. E68, o1124.],c[Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012c). Acta Cryst. E68, o2397.]). For discussion on aromatic interactions, see: Bloom & Wheeler (2011[Bloom, J. W. G. & Wheeler, S. E. (2011). Angew. Chem. Int. Ed. 50, 7847-7849.]); Martinez & Iverson (2012[Martinez, C. R. & Iverson, B. L. (2012). Chem. Sci. 3, 2191-2201.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & &Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C29H24N2O2

  • Mr = 432.50

  • Monoclinic, P 21 /n

  • a = 17.1073 (4) Å

  • b = 8.1230 (2) Å

  • c = 17.6160 (4) Å

  • [beta] = 110.325 (1)°

  • V = 2295.55 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 298 K

  • 0.30 × 0.24 × 0.18 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.]) Tmin = 0.978, Tmax = 0.986

  • 21711 measured reflections

  • 4455 independent reflections

  • 2979 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.03

  • 4455 reflections

  • 313 parameters

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

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...N1i 0.91 (2) 2.09 (2) 2.973 (2) 165.2 (17)
C56-H56...O2ii 0.978 (15) 2.411 (16) 3.371 (2) 166.9 (13)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5022 ).


Acknowledgements

The authors thank the SAIF, IIT, Chennai, for the data collection. PG thanks the CSIR, India, for a Research Fellowship. SP thanks the Department of Science and Technology, New Delhi, for funding the Indo-Spanish collaborative major research project (grant DST/INT/SPAIN/ 09).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bloom, J. W. G. & Wheeler, S. E. (2011). Angew. Chem. Int. Ed. 50, 7847-7849.  [ISI] [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.
Cremer, D. & &Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Martinez, C. R. & Iverson, B. L. (2012). Chem. Sci. 3, 2191-2201.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012a). Acta Cryst. E68, o1576.  [CSD] [CrossRef] [details]
Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012b). Acta Cryst. E68, o1124.  [CSD] [CrossRef] [details]
Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012c). Acta Cryst. E68, o2397.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3441  [ doi:10.1107/S1600536812046764 ]

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