[Journal logo]

Volume 68 
Part 1 
Pages o158-o159  
January 2012  

Received 30 November 2011
Accepted 10 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.046
wR = 0.104
Data-to-parameter ratio = 7.5
Details
Open access

3,3'-Bis(quinolin-8-yl)-1,1'-[4,4'-methylenebis(4,1-phenylene)]diurea

aDepartment of Chemistry and Biochemistry, 1400 J. R. Lynch St, PO Box 17910, Jackson State University, Jackson, MS 39217-0510, USA, and bDepartment of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Room 208, Norman, OK 73019-3051, USA
Correspondence e-mail: alamgir.hossain@jsums.edu

The title compound, C33H26N6O2, contains two 3-(quinolin-8-yl)urea groups linked to a diphenylmethane. The asymmetric unit contains two molecules, A and B. Each quinoline plane is essentially parallel to the attached urea unit [dihedral angles = 8.97 (18) and 8.81 (19) in molecule A and 18.47 (18) and 4.09 (19)° in molecule B]. The two benzene rings are twisted, making dihedral angles of 81.36 (8)° in A and 87.20 (9)° in B. The molecular structures are stabilized by intramolecular N-H...N hydrogen bonds. In the crystal, each urea O atom is involved in two N-H...O hydrogen bonds, generating two interpenetrating three-dimensional sets of molecules.

Related literature

For general background to urea-based compounds in supramolecular chemistry, see: Fan et al. (1993[Fan, E., Van Arman, S. A., Kincaid, S. & Hamilton, A. D. (1993). J. Am. Chem. Soc. 115, 369-370.]); Smith et al. (1992[Smith, P. J., Reddington, M. V. & Wilcox, C. S. (1992). Tetrahedron Lett. 33, 6085-6088.]); Pramanik et al. (2011[Pramanik, A., Thompson, B., Hayes, T., Tucker, K., Powell, D. R., Bonnesen, P. V., Ellis, E. D., Lee, K. S., Yu, H. & Hossain, M. A. (2011). Org. Biomol. Chem. 9, 4444-4447.]); Caltagirone et al. (2008[Caltagirone, C., Hiscock, J. R., Hursthouse, M. B., Light, M. E. & Gale, P. A. (2008). Chem. Eur. J. 14, 10236-10243.]); Custelcean et al. (2005[Custelcean, R., Moyer, B. A. & Hay, B. P. (2005). Chem. Commun. pp. 5971-5973.]). For related structures, see: Wu et al. (2008[Wu, B., Liang, J., Yang, J., Jia, C., Yang, X. J., Zhang, H., Tang, N. & Janiak, C. (2008). Chem. Commun. pp. 1762-1764.]); Saeed et al. (2010[Saeed, M. A., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o656-o657.]).

[Scheme 1]

Experimental

Crystal data
  • C33H26N6O2

  • Mr = 538.60

  • Tetragonal, P 43

  • a = 18.1345 (6) Å

  • c = 17.1405 (11) Å

  • V = 5636.8 (5) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.35 × 0.34 × 0.34 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.972, Tmax = 0.973

  • 65350 measured reflections

  • 5737 independent reflections

  • 4589 reflections with I > 2[sigma](I)

  • Rint = 0.104

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.104

  • S = 1.00

  • 5737 reflections

  • 767 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N11A-H11A...N1A 0.74 (4) 2.27 (4) 2.625 (4) 110 (3)
N11A-H11A...O13Ai 0.74 (4) 2.41 (4) 3.101 (3) 155 (4)
N14A-H14A...O13Ai 0.86 (4) 1.97 (4) 2.810 (4) 166 (3)
N28A-H28A...O30Aii 0.78 (4) 2.05 (4) 2.827 (4) 170 (4)
N31A-H31A...O30Aii 0.88 (4) 2.56 (4) 3.293 (4) 141 (3)
N31A-H31A...N39A 0.88 (4) 2.14 (4) 2.635 (4) 114 (3)
N11B-H11B...N1B 0.90 (4) 2.13 (4) 2.645 (4) 116 (3)
N11B-H11B...O30Biii 0.90 (4) 2.46 (4) 3.172 (4) 136 (3)
N14B-H14B...O30Biii 0.80 (3) 1.98 (4) 2.772 (4) 167 (3)
N28B-H28B...O13Biv 0.87 (4) 1.94 (4) 2.786 (4) 161 (4)
N31B-H31B...O13Biv 0.90 (4) 2.36 (3) 3.115 (4) 141 (3)
N31B-H31B...N39B 0.90 (4) 2.14 (3) 2.647 (4) 115 (3)
Symmetry codes: (i) [y, -x+1, z+{\script{1\over 4}}]; (ii) [y+1, -x+1, z+{\script{1\over 4}}]; (iii) [-y+1, x-1, z-{\script{1\over 4}}]; (iv) [-y+1, x, z-{\script{1\over 4}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: RK2320 ).


Acknowledgements

The National Science Foundation is acknowledged for a CAREER award (CHE-1056927) to MAH. The work was supported by the National Institute of Health (G12RR013459). The NMR instrument used for this work was funded by the National Science Foundation (CHE-0821357).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caltagirone, C., Hiscock, J. R., Hursthouse, M. B., Light, M. E. & Gale, P. A. (2008). Chem. Eur. J. 14, 10236-10243.  [CSD] [CrossRef] [PubMed] [ChemPort]
Custelcean, R., Moyer, B. A. & Hay, B. P. (2005). Chem. Commun. pp. 5971-5973.  [CSD] [CrossRef]
Fan, E., Van Arman, S. A., Kincaid, S. & Hamilton, A. D. (1993). J. Am. Chem. Soc. 115, 369-370.  [CrossRef] [ChemPort] [ISI]
Pramanik, A., Thompson, B., Hayes, T., Tucker, K., Powell, D. R., Bonnesen, P. V., Ellis, E. D., Lee, K. S., Yu, H. & Hossain, M. A. (2011). Org. Biomol. Chem. 9, 4444-4447.  [CSD] [CrossRef] [ChemPort]
Saeed, M. A., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o656-o657.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, P. J., Reddington, M. V. & Wilcox, C. S. (1992). Tetrahedron Lett. 33, 6085-6088.  [CrossRef] [ChemPort] [ISI]
Wu, B., Liang, J., Yang, J., Jia, C., Yang, X. J., Zhang, H., Tang, N. & Janiak, C. (2008). Chem. Commun. pp. 1762-1764.  [CSD] [CrossRef]


Acta Cryst (2012). E68, o158-o159   [ doi:10.1107/S1600536811053220 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.