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ISSN: 2056-9890

5-Iodo­pyrimidin-2-amine

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

(Received 18 May 2010; accepted 21 May 2010; online 26 May 2010)

The mol­ecule of the title compound, C4H4IN3, has crystallographic mirror plane symmetry. In the crystal, the mol­ecules are connected through N—H⋯N 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[Lin, C.-Y., Chan, Z.-K., Yeh, C.-W., Wu, C.-J., Chen, J.-D. & Wang, J.-C. (2006). CrystEngComm, 8, 841-846.]).

[Scheme 1]

Experimental

Crystal data
  • C4H4IN3

  • Mr = 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 Kα radiation

  • μ = 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[Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.332, Tmax = 1.000

  • 800 measured reflections

  • 573 independent reflections

  • 535 reflections with I > 2σ(I)

  • Rint = 0.032

  • 3 standard reflections every 97 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(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

  • Δρmax = 0.93 e Å−3

  • Δρmin = −0.83 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯N1i 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[Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

A series of Ag(I) coordination polymers containg 2-amino-5-iodopyrimidine have been prepared, which show metallocycles and one-dimensional helical chains (Lin, et al., 2006). Within this project the crystal structure of 2-amino-5-iodopyrimidine was determined to investigate its weak interactions.

In its crystal structure weak intermolecular N—H···N hydrogen bonding is found (Tab. 1) and the molecules are almost planar (Fig. 1).

Related literature top

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

Experimental top

The title compound was purchased from Acros Chemical Co. and used as received. Coloress plate crystals suitable for X-ray crystallography were obtained by dissolving the title compound in THF, followed by allowing the solution to evaporate slowly under air.

Refinement top

The pyrimidyl hydrogen atoms were placed into idealized positions and constrained by the riding atom approximation with C—H = 0.93 Å, and Uiso(H) = 1.2 Ueq(C). The amine hydrogen atoms were located from difference Fourier maps..

Structure description top

A series of Ag(I) coordination polymers containg 2-amino-5-iodopyrimidine have been prepared, which show metallocycles and one-dimensional helical chains (Lin, et al., 2006). Within this project the crystal structure of 2-amino-5-iodopyrimidine was determined to investigate its weak interactions.

In its crystal structure weak intermolecular N—H···N hydrogen bonding is found (Tab. 1) and the molecules are almost planar (Fig. 1).

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

Computing details top

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS (Siemens, 1995); data reduction: XSCANS (Siemens, 1995); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level.Symmetry codes: (i) -x, y, z.
5-Iodopyrimidin-2-amine top
Crystal data top
C4H4IN3F(000) = 816
Mr = 221.00Dx = 2.415 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 31 reflections
a = 7.9088 (7) Åθ = 4.9–12.6°
b = 8.3617 (10) ŵ = 5.16 mm1
c = 18.3821 (16) ÅT = 295 K
V = 1215.6 (2) Å3Plate, colorless
Z = 80.6 × 0.4 × 0.2 mm
Data collection top
Bruker P4
diffractometer
535 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω scansh = 19
Absorption correction: multi-scan
(XSCANS; Siemens, 1995)
k = 19
Tmin = 0.332, Tmax = 1.000l = 211
800 measured reflections3 standard reflections every 97 reflections
573 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.055P)2 + 3.1925P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
573 reflectionsΔρmax = 0.93 e Å3
48 parametersΔρmin = 0.83 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0148 (9)
Crystal data top
C4H4IN3V = 1215.6 (2) Å3
Mr = 221.00Z = 8
Orthorhombic, CmcaMo Kα radiation
a = 7.9088 (7) ŵ = 5.16 mm1
b = 8.3617 (10) ÅT = 295 K
c = 18.3821 (16) Å0.6 × 0.4 × 0.2 mm
Data collection top
Bruker P4
diffractometer
535 reflections with I > 2σ(I)
Absorption correction: multi-scan
(XSCANS; Siemens, 1995)
Rint = 0.032
Tmin = 0.332, Tmax = 1.0003 standard reflections every 97 reflections
800 measured reflections intensity decay: none
573 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.93 e Å3
573 reflectionsΔρmin = 0.83 e Å3
48 parameters
Special details top

Experimental. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I0.00000.25315 (4)0.72128 (2)0.0462 (4)
N10.1515 (4)0.6239 (4)0.57261 (16)0.0378 (8)
N20.00000.8038 (8)0.5044 (4)0.0456 (13)
C10.00000.4412 (6)0.6466 (3)0.0345 (11)
C20.1488 (5)0.5037 (4)0.6200 (2)0.0367 (9)
H2C0.25070.46040.63580.044*
C30.00000.6791 (7)0.5508 (3)0.0343 (11)
H2N0.085 (7)0.831 (7)0.485 (3)0.061 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I0.0388 (4)0.0504 (5)0.0495 (5)0.0000.0000.01869 (14)
N10.0321 (17)0.0427 (17)0.0385 (16)0.0031 (14)0.0005 (12)0.0041 (13)
N20.039 (3)0.053 (3)0.045 (3)0.0000.0000.017 (3)
C10.038 (3)0.033 (2)0.032 (2)0.0000.0000.002 (2)
C20.0329 (19)0.0406 (19)0.036 (2)0.0011 (16)0.0016 (15)0.0034 (14)
C30.041 (3)0.035 (3)0.027 (2)0.0000.0000.000 (2)
Geometric parameters (Å, º) top
I—C12.088 (5)N2—H2N0.79 (5)
N1—C21.331 (4)C1—C21.377 (4)
N1—C31.346 (4)C2—H2C0.9300
N2—C31.346 (10)
C2—N1—C3116.1 (3)N1—C2—H2C118.9
C3—N2—H2N120 (4)C1—C2—H2C118.9
C2i—C1—C2117.4 (5)N1i—C3—N1125.9 (5)
C2—C1—I121.3 (2)N1i—C3—N2117.0 (2)
N1—C2—C1122.2 (4)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1ii0.79 (5)2.37 (5)3.157 (4)173 (6)
Symmetry code: (ii) x1/2, y+3/2, z+1.

Experimental details

Crystal data
Chemical formulaC4H4IN3
Mr221.00
Crystal system, space groupOrthorhombic, Cmca
Temperature (K)295
a, b, c (Å)7.9088 (7), 8.3617 (10), 18.3821 (16)
V3)1215.6 (2)
Z8
Radiation typeMo Kα
µ (mm1)5.16
Crystal size (mm)0.6 × 0.4 × 0.2
Data collection
DiffractometerBruker P4
Absorption correctionMulti-scan
(XSCANS; Siemens, 1995)
Tmin, Tmax0.332, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
800, 573, 535
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.089, 1.10
No. of reflections573
No. of parameters48
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.93, 0.83

Computer programs: XSCANS (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.79 (5)2.37 (5)3.157 (4)173 (6)
Symmetry code: (i) x1/2, y+3/2, z+1.
 

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

First citationLin, C.-Y., Chan, Z.-K., Yeh, C.-W., Wu, C.-J., Chen, J.-D. & Wang, J.-C. (2006). CrystEngComm, 8, 841–846.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
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