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Volume 69 
Part 6 
Pages o914-o915  
June 2013  

Received 28 January 2013
Accepted 12 April 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.039
wR = 0.101
Data-to-parameter ratio = 12.6
Details
Open access

3,3'-{[(Biphenyl-2,2'-diyl)bis(methylene)]bis(oxy)}bis[N-(4-chlorophenyl)benzamide]

aOrchid Chemicals and Pharmaceuticals Limited, R&D Centre, Chennai 600 119, India,bZydus Cadila, Vadodara, India, and cPresidency College, Chennai 600 005, India
Correspondence e-mail: sarkkaraiananthan@gmail.com

In the title compound, C40H30Cl2N2O4, the two benzene rings of the biphenyl unit are twisted with respect to each other, making a dihedral angle of 73.07 (4)°. The benzene rings of the benzamide groups form dihedral angles of 77.09 (5) and 55.48 (6)° with the central biphenyl moiety. In the crystal, molecules are linked through N-H...O hydrogen bonds to form a fused R22(38) ring motif which forms a supermolecular ribbon network extending along the [100] plane. In the two 4-chlorophenyl rings, the five C atoms and their attached H atoms are disordered over two sets of sites, with site-occupancy factors of 0.657 (15):0.343 (15) and 0.509 (13):0.491 (13).

Related literature

For the pharmacological properties of benzo[c]phenanthridine derivatives, see: Clement et al. (2005[Clement, B., Weide, M., Wolschendorf, U. & Kock, I. (2005). Angew. Chem. Int. Ed. 44, 635-638.]); Stermitz et al. (1973[Stermitz, F. R., Larson, K. A. & Kim, D. K. (1973). J. Med. Chem. 16, 939-940.], 1975[Stermitz, F. R., Gillespie, J. P., Amoros, L. G., Romero, R., Stermitz, T. A., Larson, K. A., Earl, S. & Ogg, J. E. (1975). J. Med. Chem. 18, 708-713.]); Fang et al. (1993[Fang, S. D., Wang, L. K. & Hecht, S. M. (1993). J. Org. Chem. 58, 5025-5027.]); Suzuki et al. (1992[Suzuki, M., Nakanishi, T., Kogawa, O., Ishikawa, K., Kobayashi, F., Ekimoto, H. (1992). Eur. Patent 487930. ]); Kanzawa et al. (1997[Kanzawa, F., Nishio, K., Ishida, T., Fukuda, M., Kurokawa, H., Fukumoto, H., Nomoto, Y., Fukuoka, K., Bojanowski, K. & Saijo, N. (1997). Br. J. Cancer, 76, 571-581.]); Guo et al. (2007[Guo, L., Liu, X. J., Nishikawa, K. & Plunkett, W. (2007). Mol. Cancer Ther. 6, 1501-1508.]); Nissanka et al. (2001[Nissanka, A. P. K., Karunaratne, V., Bandara, B. M. R., Kumar, V., Nakanishi, T., Nishi, M., Inada, A., Tillekeratne, L. M. V., Wijesundara, D. S. A. & Gunatilaka, A. A. L. (2001). Phytochemistry, 56, 857-861.]); Lenfeld et al. (1981[Lenfeld, J., Kroutil, M., Marsalek, E., Slavik, J., Preininger, V. & Simanek, V. (1981). Planta Med. 43, 161-165.]); Ishikawa (2001[Ishikawa, T. (2001). Med. Res. Rev. 21, 61-72.]). For the synthesis of the starting material, see: Zhang et al. (2008[Zhang, M., Mao, S.-J., Lv, P., Xie, L.-G. & Xu, X.-H. (2008). Chin. J. Org. Chem. 28, 1590-1597.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C40H30Cl2N2O4

  • Mr = 673.56

  • Triclinic, [P \overline 1]

  • a = 9.4761 (2) Å

  • b = 11.9967 (3) Å

  • c = 15.9238 (4) Å

  • [alpha] = 75.944 (2)°

  • [beta] = 86.163 (1)°

  • [gamma] = 69.368 (3)°

  • V = 1643.07 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.953

  • 33102 measured reflections

  • 6937 independent reflections

  • 4799 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.101

  • S = 1.02

  • 6937 reflections

  • 551 parameters

  • 268 restraints

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.91 (1) 2.02 (1) 2.8803 (16) 160 (2)
N1-H1...O4ii 0.90 (1) 2.05 (1) 2.9443 (16) 170 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2280 ).


Acknowledgements

The authors are grateful to the X-ray Facility, IIT Madras, India, for data collection. Further thanks are due to R. Jagan of IITM, V. Silambarasan and Dr D. Velmurugan of Madras University. RR thanks Orchid Chemicals and Pharmaceuticals Ltd, for providing the laboratory and analytical facility.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Clement, B., Weide, M., Wolschendorf, U. & Kock, I. (2005). Angew. Chem. Int. Ed. 44, 635-638.  [ISI] [CrossRef] [ChemPort]
Fang, S. D., Wang, L. K. & Hecht, S. M. (1993). J. Org. Chem. 58, 5025-5027.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Guo, L., Liu, X. J., Nishikawa, K. & Plunkett, W. (2007). Mol. Cancer Ther. 6, 1501-1508.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ishikawa, T. (2001). Med. Res. Rev. 21, 61-72.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kanzawa, F., Nishio, K., Ishida, T., Fukuda, M., Kurokawa, H., Fukumoto, H., Nomoto, Y., Fukuoka, K., Bojanowski, K. & Saijo, N. (1997). Br. J. Cancer, 76, 571-581.  [CrossRef] [ChemPort] [PubMed] [ISI]
Lenfeld, J., Kroutil, M., Marsalek, E., Slavik, J., Preininger, V. & Simanek, V. (1981). Planta Med. 43, 161-165.  [CrossRef] [ChemPort] [PubMed] [ISI]
Nissanka, A. P. K., Karunaratne, V., Bandara, B. M. R., Kumar, V., Nakanishi, T., Nishi, M., Inada, A., Tillekeratne, L. M. V., Wijesundara, D. S. A. & Gunatilaka, A. A. L. (2001). Phytochemistry, 56, 857-861.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Stermitz, F. R., Gillespie, J. P., Amoros, L. G., Romero, R., Stermitz, T. A., Larson, K. A., Earl, S. & Ogg, J. E. (1975). J. Med. Chem. 18, 708-713.  [CrossRef] [PubMed] [ChemPort] [ISI]
Stermitz, F. R., Larson, K. A. & Kim, D. K. (1973). J. Med. Chem. 16, 939-940.  [CrossRef] [ChemPort] [PubMed] [ISI]
Suzuki, M., Nakanishi, T., Kogawa, O., Ishikawa, K., Kobayashi, F., Ekimoto, H. (1992). Eur. Patent 487930.
Zhang, M., Mao, S.-J., Lv, P., Xie, L.-G. & Xu, X.-H. (2008). Chin. J. Org. Chem. 28, 1590-1597.


Acta Cryst (2013). E69, o914-o915   [ doi:10.1107/S160053681301009X ]

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