A second monoclinic polymorph of (E)-phen­yl(pyridin-2-yl)methanone oxime

Rodríguez-Mora, M.I.; Reyes-Martínez, R.; Flores-Alamo, M.; García, J.J.; Morales-Morales, D.

doi:10.1107/S1600536813002377

Volume 69
Part 2
Page o310
February 2013

Received 13 January 2013
Accepted 23 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.107
Data-to-parameter ratio = 13.8
Details

A second monoclinic polymorph of (E)-phenyl(pyridin-2-yl)methanone oxime

Monserrath I. Rodríguez-Mora,^a Reyna Reyes-Martínez,^a ^* Marcos Flores-Alamo,^b Juventino J. García ^b and David Morales-Morales ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, DF, 04510, Mexico, and ^bFacultad de Química, Universidad Autónoma de México, México D. F., 04510, Mexico
Correspondence e-mail: rrm@uaem.mx

The title compound, C₁₂H₁₀N₂O, a second monoclinic polymorph of (E)-phenyl(pyridin-2-yl)methanone oxime crystallizes in the space group P2₁/n (Z = 4). The previously reported polymorph [Taga et al. (1990). Acta Cryst. C46, 2241-2243] occurs in the space group C2/c (Z = 8). In the crystal, pairs of bifurcated O-H(N,O) hydrogen bonds link the molecules into inversion dimers. The dimers are linked by C-H [pi] interactions, forming a linear arrangement. The dihedral angle between the pyridine and phenyl rings is 67.70 (8)°.

Related literature

For properties of oximes, see: Custot et al. (1996); Turner & Ciufolini (2011); Abele et al. (2003). For the use of complexes of pyridyl oximes with a variety of transition metals in supramolecular and materials chemistry, see: Shokrollahi et al. (2008); Martinez et al. (2008). For the previously reported polymorph, see: Taga et al. (1990).

Experimental

Crystal data

C₁₂H₁₀N₂O
M_r = 198.22
Monoclinic, P 2₁ /n
a = 5.6732 (4) Å
b = 23.257 (2) Å
c = 7.4516 (5) Å
= 97.743 (7)°
V = 974.21 (13) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 130 K
0.55 × 0.31 × 0.06 mm

Data collection

Agilent Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011), based on expressions derived by Clark & Reid (1995)] T_min = 0.976, T_max = 0.995
4256 measured reflections
1918 independent reflections
1559 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.107
S = 1.04
1918 reflections
139 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1DN2ⁱ	0.88 (2)	1.93 (2)	2.7696 (17)	159 (2)
O1-H1DO1ⁱ	0.88 (2)	2.61 (2)	3.225 (2)	127 (2)
C11-H11Cgⁱⁱ	0.95	2.78	3.5453 (18)	139
Symmetry codes: (i) -x, -y, -z+2; (ii) x+1, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2100 ).

Acknowledgements

RRM (postdoctoral agreement No. 290586 UNAM) would like to thank CONACYT for scholarships. The financial support of this research by CONACYT (CB2010-154732) and DGAPA-UNAM (IN201711) is gratefully acknowledged.

References

Abele, E., Abele, R. & Lukevics, E. (2003). Chem. Heterocycl. Compd, 7, 825-865.
Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
Custot, J., Boucher, J.-L., Vadon, S., Guedes, C., Dijols, S., Delaforge, M. & Mansuy, D. (1996). J. Biol. Inorg. Chem. 1, 73-82.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Martinez, J., Aiello, I., Bellusci, A., Crispini, A. & Ghedini, M. (2008). Inorg. Chim. Acta, 361, 2677-2682.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shokrollahi, A., Ghaedi, M., Rajabi, H. R. & Niband, M. S. (2008). Spectrochim. Acta Part A, 71, 655-662.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Taga, T., Uchiyama, A., Machida, K. & Miyasaka, T. (1990). Acta Cryst. C46, 2241-2243.
Turner, C. D. & Ciufolini, M. A. (2011). Arkivoc, i, 410-428.

organic compounds