2-[2-(2,6-Dichloro­anilino)phen­yl]-N′-(4-propyl­cyclo­hexyl­idene)acetohydrazide

Akkurt, M.; Nassozi, M.; Çapan, G.; Kocabalkanlı, A.; Çelik, Í.; Büyükgüngör, O.

doi:10.1107/S1600536809054695

Volume 66
Part 2
Pages o256-o257
February 2010

Received 18 December 2009
Accepted 19 December 2009
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.009 Å
Disorder in main residue
R = 0.081
wR = 0.247
Data-to-parameter ratio = 19.5
Details

2-[2-(2,6-Dichloroanilino)phenyl]-N'-(4-propylcyclohexylidene)acetohydrazide

Mehmet Akkurt,^a ^* Mebble Nassozi,^b Gültaze Çapan,^b Ayse Kocabalkanli,^b Ísmail Çelik ^c and Orhan Büyükgüngör ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacology, stanbul University, 34116 Beyazit, stanbul, Turkey,^cDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

The asymmetric unit of the title compound, C₂₃H₂₇Cl₂N₃O, contains two crystallographically independent molecules in which the dihedral angles between the benzene rings are 70.1 (3) and 63.8 (3)°. In each molecule an intramolecular N-HO hydrogen bond generates an S(7) ring. The atoms of the propyl grouping of one molecule are disordered over two orientations with occupancies of 0.666 (6) and 0.334 (6). The crystal structure is stabilized by N-HO and C-HO hydrogen-bonding interactions.

Related literature

For the pharmacological activity and biological properties of diclofenac and its derivatives, see: Gobec et al. (2005); Moser et al. (1990); Sallmann (1986); Sriram et al. (2006); Wittine et al. (2009); Zhang et al. (2009). For comparative bond lengths, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₃H₂₇Cl₂N₃O
M_r = 432.38
Monoclinic, P 2₁ /c
a = 13.0235 (6) Å
b = 15.2618 (5) Å
c = 26.6255 (12) Å
= 118.098 (3)°
V = 4668.4 (4) Å³
Z = 8
Mo K radiation
= 0.30 mm^-1
T = 296 K
0.60 × 0.34 × 0.10 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.842, T_max = 0.971
69169 measured reflections
9577 independent reflections
4744 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.081
wR(F²) = 0.247
S = 1.01
9577 reflections
492 parameters
7 restraints
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.86	2.28	2.886 (4)	128
N2-H2O2ⁱ	0.86	2.24	3.077 (5)	165
N4-H4AO2	0.86	2.32	2.921 (6)	127
N5-H5AO1ⁱⁱ	0.86	2.21	3.034 (4)	161
C20-H20AO2ⁱ	0.97	2.53	3.330 (6)	139
C36-H36BO1ⁱⁱ	0.97	2.41	3.307 (5)	155
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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: HB5287 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was also supported by the research fund of Istanbul University (project No. 3041).

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.
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Wittine, K., Benci, K., Rajic, Z., Zorc, B., Kralj, M., Marjanovic, M., Pavelic, K., De Clercq, E., Andrei, G., Snoeck, R., Balsarini, J. & Mintas, M. (2009). Eur. J. Med. Chem. 44, 143-151.
Zhang, J., Wang, J., Wu, H., He, Y., Zhu, G., Cui, X. & Tang, L. (2009). Bioorg. Med. Chem. Lett. 19, 3324-3327.

organic compounds