N-(4-Chloro­phen­yl)-4-(pyrimidin-2-yl)piperazine-1-carboxamide

Li, Y.-F.

doi:10.1107/S160053681103515X

Volume 67
Part 10
Page o2575
October 2011

Received 23 August 2011
Accepted 28 August 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.223
Data-to-parameter ratio = 17.8
Details

N-(4-Chlorophenyl)-4-(pyrimidin-2-yl)piperazine-1-carboxamide

Yu-Feng Li ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
Correspondence e-mail: liyufeng8111@163.com

The title compound, C₁₅H₁₆ClN₅O, contains two molecules, A and B, in the asymmetric unit, in which the dihedral angles between the terminal aromatic rings are 42.41 (17) and 45.77 (18)°. The central six-membered ring in both molecules has a chair conformation with equatorial substituents. In the crystal, molecules are linked into [100] C(4) chains of alternating A and B molecules by N-HO hydrogen bonds.

Related literature

For related structures, see: Li (2011a,b).

Experimental

Crystal data

C₁₅H₁₆ClN₅O
M_r = 317.78
Monoclinic, P 2₁ /c
a = 9.992 (2) Å
b = 9.978 (2) Å
c = 31.197 (6) Å
= 92.50 (3)°
V = 3107.3 (11) Å³
Z = 8
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.22 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer
29790 measured reflections
7075 independent reflections
3210 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.223
S = 0.93
7075 reflections
398 parameters
1 restraint
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3B-H3BAO1A	0.86	2.18	3.030 (3)	172
N3A-H3AAO1Bⁱ	0.86	2.26	3.090 (3)	163
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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: HB6389 ).

References

Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
Li, Y.-F. (2011a). Acta Cryst. E67, o1796.
Li, Y.-F. (2011b). Acta Cryst. E67, o1792.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds