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

Pramanik, A.; Russ, T.H.; Powell, D.R.; Hossain, M.A.

doi:10.1107/S1600536811053220

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 (C-C) = 0.005 Å
R = 0.046
wR = 0.104
Data-to-parameter ratio = 7.5
Details

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

Avijit Pramanik,^a Tiffany H. Russ,^a Douglas R. Powell ^b and Md. Alamgir Hossain ^a ^*

^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-HN hydrogen bonds. In the crystal, each urea O atom is involved in two N-HO 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); Smith et al. (1992); Pramanik et al. (2011); Caltagirone et al. (2008); Custelcean et al. (2005). For related structures, see: Wu et al. (2008); Saeed et al. (2010).

Experimental

Crystal data

C₃₃H₂₆N₆O₂
M_r = 538.60
Tetragonal, P 4₃
a = 18.1345 (6) Å
c = 17.1405 (11) Å
V = 5636.8 (5) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.972, T_max = 0.973
65350 measured reflections
5737 independent reflections
4589 reflections with I > 2(I)
R_int = 0.104

Refinement

R[F² > 2(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
_max = 0.16 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11A-H11AN1A	0.74 (4)	2.27 (4)	2.625 (4)	110 (3)
N11A-H11AO13Aⁱ	0.74 (4)	2.41 (4)	3.101 (3)	155 (4)
N14A-H14AO13Aⁱ	0.86 (4)	1.97 (4)	2.810 (4)	166 (3)
N28A-H28AO30Aⁱⁱ	0.78 (4)	2.05 (4)	2.827 (4)	170 (4)
N31A-H31AO30Aⁱⁱ	0.88 (4)	2.56 (4)	3.293 (4)	141 (3)
N31A-H31AN39A	0.88 (4)	2.14 (4)	2.635 (4)	114 (3)
N11B-H11BN1B	0.90 (4)	2.13 (4)	2.645 (4)	116 (3)
N11B-H11BO30Bⁱⁱⁱ	0.90 (4)	2.46 (4)	3.172 (4)	136 (3)
N14B-H14BO30Bⁱⁱⁱ	0.80 (3)	1.98 (4)	2.772 (4)	167 (3)
N28B-H28BO13B^iv	0.87 (4)	1.94 (4)	2.786 (4)	161 (4)
N31B-H31BO13B^iv	0.90 (4)	2.36 (3)	3.115 (4)	141 (3)
N31B-H31BN39B	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Custelcean, R., Moyer, B. A. & Hay, B. P. (2005). Chem. Commun. pp. 5971-5973.
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Saeed, M. A., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o656-o657.
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Wu, B., Liang, J., Yang, J., Jia, C., Yang, X. J., Zhang, H., Tang, N. & Janiak, C. (2008). Chem. Commun. pp. 1762-1764.

organic compounds