1-(2-Ureidoeth­yl)quinolinium tetra­phenyl­borate

Dong, Z.-Y.; Yang, Y.; Gao, G.-H.

doi:10.1107/S1600536811027218

Volume 67
Part 8
Page o2031
August 2011

Received 28 June 2011
Accepted 7 July 2011
Online 13 July 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.070
Data-to-parameter ratio = 7.3
Details

1-(2-Ureidoethyl)quinolinium tetraphenylborate

Zhi-Yun Dong,^a Yu Yang ^a and Guo-Hua Gao ^a ^*

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, People's Republic of China
Correspondence e-mail: ghgao@chem.ecnu.edu.cn

In the cation of the title salt, C₁₂H₁₄N₃O⁺·C₂₄H₂₀B^-, the dihedral angle between the quinoline ring and the mean plane of the urea fragment is 61.51 (5)°. In the crystal, the cations interact through weak C-HO hydrogen bonding, forming a zigzag chain along the c-axis direction; the cations and anions are involved in weak intermolecular C-H [pi] and N-H [pi] interactions as donors and acceptors, respectively.

Related literature

For applications of ionic liquids, see: Zhao & Malhotra (2002); Chauvin & Olivier-Bourbigou (1995); Seddon (2001); Hapiot & Lagros (2008); Blaster & Studer (2003). For a related structure, see: Youngme et al. (2006).

Experimental

Crystal data

C₁₂H₁₄N₃O⁺·C₂₄H₂₀B^-
M_r = 535.47
Orthorhombic, A b a 2
a = 25.5434 (11) Å
b = 18.7954 (8) Å
c = 12.0837 (5) Å
V = 5801.4 (4) Å³
Z = 8
Mo K radiation
= 0.07 mm^-1
T = 173 K
0.40 × 0.18 × 0.13 mm

Data collection

Rigaku Saturn CCD diffractometer
32920 measured reflections
2700 independent reflections
2428 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.070
S = 1.06
2700 reflections
370 parameters
1 restraint
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C7-C12 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C30-H30AO1ⁱ	0.95	2.30	3.173 (3)	153
N2-H2BCg2ⁱⁱ	0.88	2.62	3.483 (2)	168
C26-H26ACg1ⁱⁱⁱ	0.95	2.61	3.438 (3)	146
C27-H27ACg2^iv	0.95	2.68	3.572 (3)	157
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: XU5255 ).

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant Nos. 20873041 and 21072061) and the Shanghai Leading Academic Discipline Project (grant No. B409) for financial support.

References

Blaster, H. U. & Studer, M. (2003). Green Chem. 5, 112-117.
Chauvin, Y. & Olivier-Bourbigou, H. (1995). Chemtech, 25, 26-30.
Hapiot, P. & Lagros, C. (2008). Chem. Rev. 108, 2238-2264.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Seddon, K. R. (2001). Chem. Commun. 23, 2399-2407.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Youngme, S., Wannarit, N. & Chaichit, N. (2006). Acta Cryst. E62, o5265-o5267.
Zhao, H. & Malhotra, S. V. (2002). Aldrichim. Acta, 35, 75-83.

organic compounds