5-Iodo­pyrimidin-2-amine

Chiang, Y.-H.; Wu, C.-J.; Cheng, P.-C.; Chen, J.-D.

doi:10.1107/S1600536810019124

Volume 66
Part 6
Page o1464
June 2010

Received 18 May 2010
Accepted 21 May 2010
Online 26 May 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.032
wR = 0.089
Data-to-parameter ratio = 11.9
Details

5-Iodopyrimidin-2-amine

Yen-Hsun Chiang,^a Chia-Jun Wu,^a Pei-Chi Cheng ^a and Jhy-Der Chen ^a ^*

^aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li, Taiwan
Correspondence e-mail: jdchen@cycu.edu.tw

The molecule of the title compound, C₄H₄IN₃, has crystallographic mirror plane symmetry. In the crystal, the molecules are connected through N-HN hydrogen bonds into polymeric tapes extended along the a axis, which are typical of 2-aminopyrimidines. Each molecule acts as a double donor and a double acceptor in the hydrogen bonding.

Related literature

For coordination polymers formed with the title compound, see: Lin et al. (2006).

Experimental

Crystal data

C₄H₄IN₃
M_r = 221.00
Orthorhombic, C m c a
a = 7.9088 (7) Å
b = 8.3617 (10) Å
c = 18.3821 (16) Å
V = 1215.6 (2) Å³
Z = 8
Mo K radiation
= 5.16 mm^-1
T = 295 K
0.6 × 0.4 × 0.2 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (XSCANS; Siemens, 1995) T_min = 0.332, T_max = 1.000
800 measured reflections
573 independent reflections
535 reflections with I > 2(I)
R_int = 0.032
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.089
S = 1.10
573 reflections
48 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.93 e Å^-3
_min = -0.83 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NN1ⁱ	0.79 (5)	2.37 (5)	3.157 (4)	173 (6)
Symmetry code: (i) $[-x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in 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: GK2275 ).

Acknowledgements

We are grateful to the National Science Council of the Republic of China for support. This research was also supported by the project of specific research fields in Chung-Yuan Christian University, Taiwan, under grant No. CYCU-98-CR-CH.

References

Lin, C.-Y., Chan, Z.-K., Yeh, C.-W., Wu, C.-J., Chen, J.-D. & Wang, J.-C. (2006). CrystEngComm, 8, 841-846.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds