N-(2-Hy­droxy­eth­yl)-5-(4-meth­oxy­phen­yl)-4H-pyrazole-3-carboxamide

Han, G.; Lv, J.; Zhu, J.; Zhou, Y.; Wu, D.

doi:10.1107/S1600536812007829

Volume 68
Part 3
Page o901
March 2012

Received 14 February 2012
Accepted 21 February 2012
Online 29 February 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.156
Data-to-parameter ratio = 13.5
Details

N-(2-Hydroxyethyl)-5-(4-methoxyphenyl)-4H-pyrazole-3-carboxamide

Guangqian Han,^a Jiaguo Lv,^b ^* Ju Zhu,^b Youjun Zhou ^b and Defeng Wu ^a ^*

^aDepartment of Pharmacognosy, School of Food Science, Fujian Agriculture and Forestry University, Fujian 350002, People's Republic of China, and ^bDepartment of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China
Correspondence e-mail: ljg20060508@yahoo.com.cn, zi99289@yeah.net

In the title compound, C₁₃H₁₅N₃O₃, the dihedral angle between the benzene and pyrazole rings is 7.7 (1)° and the O-C-C-N torsion angle of the side chain is 74.1 (2)°. In the crystal, molecules are linked by O-HO, N-HO and N-HN hydrogen bonds.

Related literature

For the biological activities of pyrazole derivatives, see: Qi et al. (2011). For a related structure, see: Shi & Xie (2011).

Experimental

Crystal data

C₁₃H₁₅N₃O₃
M_r = 261.28
Monoclinic, C 2/c
a = 21.82 (5) Å
b = 10.08 (2) Å
c = 12.28 (3) Å
= 110.53 (3)°
V = 2531 (11) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.20 × 0.15 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.980, T_max = 0.994
5292 measured reflections
2366 independent reflections
1841 reflections with I > 2(I)
R_int = 0.074

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.156
S = 1.05
2366 reflections
175 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O2ⁱ	0.82	1.88	2.668 (5)	162
N3-H3BN2ⁱⁱ	0.86	2.54	3.318 (7)	151
N1-H1DO3ⁱⁱ	0.86	1.90	2.739 (5)	166
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: HB6641 ).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Qi, J. J., Zhu, J., Liu, X. F., Ding, L. L., Zheng, C. H., Han, G. Q., Lv, J. G. & Zhou, Y. J. (2011). Bioorg. Med. Chem. Lett. 21, 5822-5825.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, C.-X. & Xie, Y.-M. (2011). Acta Cryst. E67, o1084.

organic compounds