1,3-Bis(2-anilino-2-oxoeth­yl)-1H-imidazol-3-ium chloride dimethyl­formamide monosolvate

Lee, H.M.; Zeng, J.-Y.

doi:10.1107/S1600536812045059

Volume 68
Part 12
Page o3286
December 2012

Received 25 October 2012
Accepted 31 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.091
Data-to-parameter ratio = 20.1
Details

1,3-Bis(2-anilino-2-oxoethyl)-1H-imidazol-3-ium chloride dimethylformamide monosolvate

Hon Man Lee ^a ^* and Jing-Yao Zeng ^a

^aDepartment of Chemistry, National Changhua University of Education, Changhua, Taiwan 50058
Correspondence e-mail: leehm@cc.ncue.edu.tw

In the imidazolium cation of the title compound, C₁₉H₁₉N₄O₂⁺·Cl^-·C₃H₇NO, the dihedral angles between the imidazole ring and the phenyl rings are 85.86 (4) and 70.26 (5)°. In the crystal, N-HCl hydrogen bonds link the imdiazolium cations and chloride anions into zigzag chains along [110] and together with C-HCl and C-HO hydrogen bonds, which involve also the dimethylformamide solvent molecule, form a two-dimensional network extending across the ab plane.

Related literature

For the crystal structures of the non-solvated title compound and an acetonitrile monosolvate, see: Liao & Lee (2012) and Liao & Lee (2011), respectively. For the crystal structures of nickel, palladium, and silver complexes with ligands derived from the title compound, see: Liao, Chan, Chang et al. (2007), Liao, Chan, Zeng et al. (2007) and Liao et al. (2008), respectively.

Experimental

Crystal data

C₁₉H₁₉N₄O₂⁺·Cl^-·C₃H₇NO
M_r = 443.93
Triclinic, $[P \overline 1]$
a = 9.2352 (5) Å
b = 9.9907 (5) Å
c = 14.0805 (7) Å
= 109.119 (3)°
= 96.342 (3)°
= 107.224 (3)°
V = 1141.05 (11) Å³
Z = 2
Mo K radiation
= 0.20 mm^-1
T = 150 K
0.50 × 0.32 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.883, T_max = 0.957
13404 measured reflections
5676 independent reflections
4849 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.091
S = 1.06
5676 reflections
282 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4Cl1ⁱ	0.88	2.39	3.2696 (10)	174
N5-H5Cl1ⁱⁱ	0.88	2.35	3.2292 (10)	172
C1-H1O4ⁱⁱⁱ	0.95	2.32	3.0910 (14)	138
C2-H2O3^iv	0.95	2.49	3.1619 (13)	128
C12-H12ACl1	0.99	2.63	3.4269 (12)	137
C12-H12BO3^iv	0.99	2.44	3.1544 (14)	129
C20-H20AO4^iv	0.99	2.52	3.2790 (15)	133
C23-H23AO1^iv	0.98	2.53	3.3472 (18)	141
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (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: DIAMOND (Brandenburg, 2006).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2241 ).

Acknowledgements

We thank the National Science Council of Taiwan for financial support of this work.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Liao, C.-Y., Chan, K.-T., Chang, Y.-C., Chen, C.-Y., Tu, C.-Y., Hu, C.-H. & Lee, H. M. (2007). Organometallics, 26, 5826-5833.
Liao, C.-Y., Chan, K.-T., Chiu, P.-L., Chen, C.-Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.
Liao, C.-Y., Chan, K.-T., Zeng, J.-Y., Hu, C.-H., Tu, C.-Y. & Lee, H. M. (2007). Organometallics, 26, 1692-1702.
Liao, C.-Y. & Lee, H. M. (2011). Acta Cryst. E67, o3362.
Liao, C.-Y. & Lee, H. M. (2012). Acta Cryst. E68, o2232.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds