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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 [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.091
Data-to-parameter ratio = 20.1
Details
Open access

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

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-H...Cl hydrogen bonds link the imdiazolium cations and chloride anions into zigzag chains along [110] and together with C-H...Cl and C-H...O 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[Liao, C.-Y. & Lee, H. M. (2012). Acta Cryst. E68, o2232.]) and Liao & Lee (2011[Liao, C.-Y. & Lee, H. M. (2011). Acta Cryst. E67, o3362.]), 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, 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, Chan, Zeng et al. (2007[Liao, C.-Y., Chan, K.-T., Zeng, J.-Y., Hu, C.-H., Tu, C.-Y. & Lee, H. M. (2007). Organometallics, 26, 1692-1702.]) and Liao et al. (2008[Liao, C.-Y., Chan, K.-T., Chiu, P.-L., Chen, C.-Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C19H19N4O2+·Cl-·C3H7NO

  • Mr = 443.93

  • Triclinic, [P \overline 1]

  • a = 9.2352 (5) Å

  • b = 9.9907 (5) Å

  • c = 14.0805 (7) Å

  • [alpha] = 109.119 (3)°

  • [beta] = 96.342 (3)°

  • [gamma] = 107.224 (3)°

  • V = 1141.05 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.883, Tmax = 0.957

  • 13404 measured reflections

  • 5676 independent reflections

  • 4849 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.091

  • S = 1.06

  • 5676 reflections

  • 282 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...Cl1i 0.88 2.39 3.2696 (10) 174
N5-H5...Cl1ii 0.88 2.35 3.2292 (10) 172
C1-H1...O4iii 0.95 2.32 3.0910 (14) 138
C2-H2...O3iv 0.95 2.49 3.1619 (13) 128
C12-H12A...Cl1 0.99 2.63 3.4269 (12) 137
C12-H12B...O3iv 0.99 2.44 3.1544 (14) 129
C20-H20A...O4iv 0.99 2.52 3.2790 (15) 133
C23-H23A...O1iv 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).


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.  [CSD] [CrossRef] [ChemPort]
Liao, C.-Y., Chan, K.-T., Chiu, P.-L., Chen, C.-Y. & Lee, H. M. (2008). Inorg. Chim. Acta, 361, 2973-2978.  [ISI] [CSD] [CrossRef] [ChemPort]
Liao, C.-Y., Chan, K.-T., Zeng, J.-Y., Hu, C.-H., Tu, C.-Y. & Lee, H. M. (2007). Organometallics, 26, 1692-1702.  [CSD] [CrossRef] [ChemPort]
Liao, C.-Y. & Lee, H. M. (2011). Acta Cryst. E67, o3362.  [CSD] [CrossRef] [details]
Liao, C.-Y. & Lee, H. M. (2012). Acta Cryst. E68, o2232.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3286  [ doi:10.1107/S1600536812045059 ]

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