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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.
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.
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019124/gk2275sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019124/gk2275Isup2.hkl
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.
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.
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..
|C4H4IN3||F(000) = 816|
|Mr = 221.00||Dx = 2.415 Mg m−3|
|Orthorhombic, Cmca||Mo Kα radiation, λ = 0.71073 Å|
|Hall symbol: -C 2bc 2||Cell parameters from 31 reflections|
|a = 7.9088 (7) Å||θ = 4.9–12.6°|
|b = 8.3617 (10) Å||µ = 5.16 mm−1|
|c = 18.3821 (16) Å||T = 295 K|
|V = 1215.6 (2) Å3||Plate, colorless|
|Z = 8||0.6 × 0.4 × 0.2 mm|
|Bruker P4 diffractometer||535 reflections with I > 2σ(I)|
|Radiation source: fine-focus sealed tube||Rint = 0.032|
|graphite||θmax = 25.0°, θmin = 2.2°|
|ω scans||h = −1→9|
|Absorption correction: multi-scan (XSCANS; Siemens, 1995)||k = −1→9|
|Tmin = 0.332, Tmax = 1.000||l = −21→1|
|800 measured reflections||3 standard reflections every 97 reflections|
|573 independent reflections||intensity decay: none|
|Refinement on F2||Secondary atom site location: difference Fourier map|
|Least-squares matrix: full||Hydrogen site location: inferred from neighbouring sites|
|R[F2 > 2σ(F2)] = 0.032||H 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 reflections||Δρmax = 0.93 e Å−3|
|48 parameters||Δρmin = −0.83 e Å−3|
|0 restraints||Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4|
|Primary atom site location: structure-invariant direct methods||Extinction coefficient: 0.0148 (9)|
|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.|
|I||0.0000||0.25315 (4)||0.72128 (2)||0.0462 (4)|
|N1||−0.1515 (4)||0.6239 (4)||0.57261 (16)||0.0378 (8)|
|N2||0.0000||0.8038 (8)||0.5044 (4)||0.0456 (13)|
|C1||0.0000||0.4412 (6)||0.6466 (3)||0.0345 (11)|
|C2||−0.1488 (5)||0.5037 (4)||0.6200 (2)||0.0367 (9)|
|C3||0.0000||0.6791 (7)||0.5508 (3)||0.0343 (11)|
|H2N||−0.085 (7)||0.831 (7)||0.485 (3)||0.061 (15)*|
|I||0.0388 (4)||0.0504 (5)||0.0495 (5)||0.000||0.000||0.01869 (14)|
|N1||0.0321 (17)||0.0427 (17)||0.0385 (16)||0.0031 (14)||0.0005 (12)||0.0041 (13)|
|N2||0.039 (3)||0.053 (3)||0.045 (3)||0.000||0.000||0.017 (3)|
|C1||0.038 (3)||0.033 (2)||0.032 (2)||0.000||0.000||0.002 (2)|
|C2||0.0329 (19)||0.0406 (19)||0.036 (2)||−0.0011 (16)||0.0016 (15)||0.0034 (14)|
|C3||0.041 (3)||0.035 (3)||0.027 (2)||0.000||0.000||0.000 (2)|
|I—C1||2.088 (5)||N2—H2N||0.79 (5)|
|N1—C2||1.331 (4)||C1—C2||1.377 (4)|
|C2i—C1—C2||117.4 (5)||N1i—C3—N1||125.9 (5)|
|C2—C1—I||121.3 (2)||N1i—C3—N2||117.0 (2)|
Symmetry codes: (i) −x, y, z.
|N2—H2N···N1ii||0.79 (5)||2.37 (5)||3.157 (4)||173 (6)|
Symmetry codes: (ii) −x−1/2, −y+3/2, −z+1.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2275).