2-Amino-4-(4-hy­droxy-3,5-dimeth­oxy­phen­yl)-6-phenyl­nicotinonitrile

Yang, X.-H.; Zhou, Y.-H.; Hu, L.-H.; Liu, H.-J.

doi:10.1107/S1600536810039127

Volume 66
Part 11
Page o2746
November 2010

Received 15 September 2010
Accepted 30 September 2010
Online 9 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.069
wR = 0.169
Data-to-parameter ratio = 13.0
Details

2-Amino-4-(4-hydroxy-3,5-dimethoxyphenyl)-6-phenylnicotinonitrile

Xiao-Hui Yang,^a Yong-Hong Zhou,^a ^* Li-Hong Hu ^a and Hong-Jun Liu ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
Correspondence e-mail: yhzhou1966@yahoo.com.cn

In the title compound, C₂₀H₁₇N₃O₃, the dihedral angles between the central pyridine ring and the two terminal rings are 15.07 (3) and 43.24 (3)°. The dihedral angle between the two terminal rings is 37.49 (4)° In the crystal, intermolecular amine N-HN_nitrile hydrogen-bonding interactions form inversion dimers, which are linked into chains through amine N-HO_methoxy hydrogen bonds.

Related literature

For literature on the biological applications of nicotine derivatives, see Hökelek & Necefouglu (1996, 1999). For literature on molecules containing the cyanopyridine moiety and their ability to act as ligands towards transition metal ions and new drugs, see: Alyoubi (2000); Desai & Shah (2003); Murata et al. (2004). For a related structure, see: Fun et al. (1996).

Experimental

Crystal data

C₂₀H₁₇N₃O₃
M_r = 347.37
Triclinic, $[P \overline 1]$
a = 8.1320 (16) Å
b = 10.497 (2) Å
c = 10.914 (2) Å
= 77.28 (3)°
= 68.36 (3)°
= 84.66 (3)°
V = 844.6 (3) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 four-circle diffractometer
Absorption correction: scan (semi-empirical, using intensity measurements; North et al., 1968) T_min = 0.981, T_max = 0.991
3294 measured reflections
3058 independent reflections
1776 reflections with I > 2(I)
R_int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.169
S = 1.01
3058 reflections
235 parameters
H-atom parameters constrained
_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
N2-H2AO2ⁱ	0.86	2.27	3.101 (4)	162
N2-H2BN3ⁱⁱ	0.86	2.31	3.098 (5)	152
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2068 ).

Acknowledgements

This work was supported by the President of the Chinese Academy of Forestry Foundation (grant No. CAFYBB2008009).

References

Alyoubi, A. O. (2000). Spectrochim. Acta, A56, 2397-2404.
Bruker (2004). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Desai, J. M. & Shah, V. H. (2003). Indian J. Chem. Sect. B, 42, 382-385.
Fun, H.-K., Sivakumar, K., Lu, Z.-L., Duan, C.-Y., Tian, Y.-P. & You, X.-Z. (1996). Acta Cryst. C52, 986-988.
Hökelek, T. & Necefouglu, H. (1996). Acta Cryst. C52, 1128-1131.
Hökelek, T. & Necefouglu, H. (1999). Acta Cryst. C55, 1438-1440.
Murata, T., et al. (2004). Bioorg. Med. Chem. Lett. 14, 4019-4022.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds