1,3-Bis(4-methoxy­phen­yl)imidazolidium chloride monohydrate

Wan, Y.; Xin, H.; Chen, X.; Xu, H.; Wu, H.

doi:10.1107/S1600536808033965

Volume 64
Part 11
Page o2159
November 2008

Received 27 September 2008
Accepted 17 October 2008
Online 22 October 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.029
wR = 0.076
Data-to-parameter ratio = 7.0
Details

1,3-Bis(4-methoxyphenyl)imidazolidium chloride monohydrate

Yu Wan,^a Haiqiang Xin,^a Xiumei Chen,^a Huahong Xu ^a and Hui Wu ^a ^*

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
Correspondence e-mail: wuhui72@yahoo.com.cn

The asymmetric unit of the title compound, C₁₇H₁₇N₂O₂⁺·Cl^-·H₂O, contains one-half of the cation, one-half of a water molecule and a chloride anion. The complete cation is generated by crystallographic two-fold symmetry, with one C atom lying on the rotation axis. The O and Cl atoms have site symmetry 2. The imidazolidium ring is oriented at a dihedral angle of 4.15 (3)° with respect to the 4-methoxyphenyl ring and an intramolecular C-HO interaction occurs. In the crystal structure, intermolecular O-HCl and C-HCl hydrogen bonds link the molecules. There is a [pi] - [pi] contact between the imidazolidium and 4-methoxyphenyl rings [centroid-to-centroid distance = 3.625(3 Å]. There is also a C-H [pi] contact between the methyl group and the 4-methoxyphenyl ring.

Related literature

For general background, see: Lin & Vasam (2005). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₇N₂O₂⁺·Cl^-·H₂O
M_r = 334.79
Monoclinic, C 2
a = 15.6706 (19) Å
b = 9.4198 (9) Å
c = 5.4026 (4) Å
= 90.156 (1)°
V = 797.50 (14) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 298 (2) K
0.20 × 0.11 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.951, T_max = 0.977
2026 measured reflections
749 independent reflections
688 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.076
S = 1.01
749 reflections
107 parameters
1 restraint
H-atom parameters constrained
_max = 0.11 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3-C8 ring.

D-HA	D-H	HA	DA	D-HA
O2-H2Cl1	0.85	2.29	3.133 (3)	173
C1-H1O2	0.93	2.13	3.060 (3)	180
C2-H2ACl1ⁱ	0.93	2.69	3.474 (3)	142
C4-H4O2	0.93	2.47	3.391 (3)	170
C9-H9CCg2ⁱⁱ	0.96	2.91	3.629 (3)	133
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x, y, z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2542 ).

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (grant No. 20772103), the Natural Science Foundation of Jiangsu Province (grant No. BK 2007028) and the Surpassing Project of Jiangsu Province (grant No. CX07S_016z) for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Lin, I. J. B. & Vasam, C. S. (2005). J. Organomet. Chem. 690, 3498-3512.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds