(Z)-1-(3-Mesityl-3-methyl­cyclo­but­yl)-2-(morpholin-4-yl)ethanone oxime

Şen, F.; Dinçer, M.; Çukurovalı, A.; Yılmaz, I.

doi:10.1107/S1600536811009408

Volume 67
Part 4
Pages o958-o959
April 2011

Received 28 February 2011
Accepted 11 March 2011
Online 23 March 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.171
Data-to-parameter ratio = 18.6
Details

(Z)-1-(3-Mesityl-3-methylcyclobutyl)-2-(morpholin-4-yl)ethanone oxime

Fatih Sen,^a ^* Muharrem Dinçer,^a Alaaddin Çukurovali ^b and Ibrahim Yilmaz ^c

^aDepartment of Physics, Arts and Sciences Faculty, Ondokuz Mayis University, 55139 Samsun, Turkey,^bDepartment of Chemistry, Sciences Faculty, Firat University, 23119 Elazig, Turkey, and ^cDepartment of Chemistry, Faculty of Science, Karamanoglu Mehmetbey University, 70200 Karaman, Turkey
Correspondence e-mail: fatihsen55@gmail.com

In the title compound, C₂₀H₃₀N₂O₂, the cyclobutane ring is puckered, with a dihedral angle of 19.60 (13)° between the two planes. In the crystal, the molecules are linked by intermolecular O-HN and weak C-HO hydrogen bonds, as well as a C-H [pi] hydrogen-bonding association.

Related literature

For applications of related compounds, see: Dehmlow & Schmidt (1990); Coghi et al. (1976); Mixich & Thiele (1979); Migrdichian (1957); Mathison et al. (1989); Polak (1982); Balsamo et al., 1990; Holan et al. (1984); Marsman et al. (1999); Forman (1964); Bertolasi et al. (1982); Gilli et al. (1983); Hökelek et al. (2001). For related structures, see: Özdemir et al. (2004); Dinçer et al. (2004). For the puckering of the cyclobutane ring, see: Swenson et al. (1997).

Experimental

Crystal data

C₂₀H₃₀N₂O₂
M_r = 330.46
Monoclinic, P 2₁ /c
a = 13.0273 (4) Å
b = 10.2337 (2) Å
c = 18.1262 (6) Å
= 126.574 (2)°
V = 1940.69 (10) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 296 K
0.60 × 0.55 × 0.48 mm

Data collection

Stoe IPDS II CCD area-detector diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.964, T_max = 0.977
28812 measured reflections
4031 independent reflections
3110 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.171
S = 1.09
4031 reflections
217 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring.

D-HA	D-H	HA	DA	D-HA
O1-H1N1ⁱ	0.82	2.11	2.7944 (19)	141
C16-H16BO2ⁱⁱ	0.97	2.55	3.494 (2)	165
C19-H19BO1ⁱⁱⁱ	0.97	2.56	3.305 (3)	134
C12-H12BCg1^iv	0.97	2.84	3.777 (3)	161
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2100 ).

Acknowledgements

This study was supported financially by the Research Center of Ondokuz Mayis University (Project No. F-461).

References

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