1-(3-Chloro­phen­yl)-3-(1-p-tolyl­imidazolidin-2-yl­idene)urea

Wysocki, W.; Matosiuk, D.; Karczmarzyk, Z.; Fidecka, S.; Fruziński, A.

doi:10.1107/S1600536808040701

Volume 65
Part 1
Page o40
January 2009

Received 1 December 2008
Accepted 3 December 2008
Online 6 December 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.165
Data-to-parameter ratio = 16.2
Details

1-(3-Chlorophenyl)-3-(1-p-tolylimidazolidin-2-ylidene)urea

Waldemar Wysocki,^a ^* Dariusz Matosiuk,^b Zbigniew Karczmarzyk,^a Sylwia Fidecka ^c and Andrzej Fruzinski ^d

^aDepartment of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland,^bDepartment of Synthesis and Chemical Technology of Pharmaceutical Substances, Medical University, ul. Staszica 6, 20-081 Lublin, Poland,^cDepartment of Pharmacology and Pharmacodynamics, Medical University, ul. Staszica 4, 20-081 Lublin, Poland, and ^dInstitute of General and Ecological Chemistry, Technical University, ul. Zwirki 115, 90-924 Lodz, Poland
Correspondence e-mail: wwysocki@ap.siedlce.pl

In the crystal structure of the title compound, C₁₇H₁₇ClN₄O, the existence of only one 2-imino-oxo of the five possible N-amino-imino/O-keto-hydroxy tautomers is observed and the dihedral angle between the aromatic rings is 29.78 (11)°. The molecular conformation is stabilized by intramolecular C-HN, N-HO and C-HO hydrogen bonds, in each case generating a six-membered ring. In the crystal structure, the glide-plane-related molecules are linked into C(4) amide chains by intermolecular N-HO hydrogen bonds, and an intermolecular C-HO link also occurs.

Related literature

For general background, synthesis, biological activity and related structures, see: Matosiuk et al. (2001, 2005); Karczmarzyk et al. (2004); Wysocki et al. (2006). For hydrogen-bond motifs, see: Steiner (2002); Bernstein et al. (1995).

Experimental

Crystal data

C₁₇H₁₇ClN₄O
M_r = 328.80
Monoclinic, P 2₁ /c
a = 11.4506 (8) Å
b = 15.5097 (17) Å
c = 9.2811 (11) Å
= 100.506 (8)°
V = 1620.7 (3) Å³
Z = 4
Cu K radiation
= 2.17 mm^-1
T = 293 (2) K
0.5 × 0.4 × 0.1 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.398, T_max = 0.805
4241 measured reflections
3485 independent reflections
2703 reflections with I > 2(I)
R_int = 0.022
2 standard reflections every 100 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.165
S = 1.05
3485 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.37 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H31O8	0.81 (3)	1.98 (3)	2.611 (2)	134 (3)
C26-H261N6	0.93	2.33	2.919 (3)	121
C32-H321O8	0.93	2.26	2.864 (3)	122
N9-H91O8ⁱ	0.93 (3)	2.01 (3)	2.927 (2)	171 (2)
C36-H361O8ⁱ	0.93	2.49	3.266 (2)	141
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: KM4B8 (Galdecki et al., 1996 $[Galdecki, Z., Kowalski, A., Kucharczyk, D. & Uszynski, I. (1996). KM4B8. Kuma Diffraction, Wroclaw, Poland.]$ ); cell refinement: KM4B8; data reduction: DATAPROC (Galdecki et al., 1995 $[Galdecki, Z., Kowalski, A. & Uszynski, L. (1995). DATAPROC. Kuma Diffraction, Wroclaw, Poland.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2873 ).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Galdecki, Z., Kowalski, A., Kucharczyk, D. & Uszynski, I. (1996). KM4B8. Kuma Diffraction, Wroclaw, Poland.
Galdecki, Z., Kowalski, A. & Uszynski, L. (1995). DATAPROC. Kuma Diffraction, Wroclaw, Poland.
Karczmarzyk, Z., Matosiuk, D., Wysocki, W. & Urbanczyk-Lipkowska, Z. (2004). Anal. Sci. (X-Ray Struct. Anal. Online), 20, x129-x130.
Matosiuk, D., Fidecka, S., Antkiewicz-Michaluk, L., Dybala, I. & Koziol, A. E. (2001). Eur. J. Med. Chem. 36, 783-797.
Matosiuk, D., Karczmarzyk, Z., Krycki, A. & Fruzinski, A. (2005). Anal. Sci. (X-Ray Struct. Anal. Online), 21, x19-x20.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.
Wysocki, W., Matosiuk, D., Karczmarzyk, Z., Rzadkowska, M. & Urbanczyk-Lipkowska, Z. (2006). Acta Cryst. E62, o2548-o2550.

organic compounds