2-Iodo-4,6-dimethyl-pyrimidine.

In the title compound, C(6)H(7)IN(2), the non-H atoms of the mol-ecule are located on a crystallographic mirror plane; the H atoms of the methyl groups are therefore disordered over two positions of equal occupancy. In the crystal structure, short inter-molecular I⋯N contacts [3.390 (3) Å] are found, linking the mol-ecules into zigzag chains. In addition, there are inter-molecular π-π stacking inter-actions between the pyrimidine rings of adjacent mol-ecules [centroid-centroid distance = 3.5168 (10) Å], resulting in a two-dimensional supra-molecular architecture.

Related literature

For applications of pyrimidine derivatives, see: Chinchilla et al. (2004 ▶); Xu et al. (2009a ▶,b ▶). For halogen–electronegative atom inter­actions, see: Lommerse et al. (1996 ▶). For the synthesis of 4,6-dimethyl-2-chloro­pyrimidine, see: Kosolapoff & Roy (1961 ▶) and literature cited therein.

Experimental

Crystal data

C6H7IN2

M = 234.04

Orthorhombic,

a = 7.930 (2) Å

b = 7.0256 (19) Å

c = 14.499 (4) Å

V = 807.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.88 mm−1

T = 296 K

0.32 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.370, T max = 0.496

5541 measured reflections

817 independent reflections

739 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.066

S = 1.10

817 reflections

57 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005660/si2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005660/si2242Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H7IN2	Dx = 1.924 Mg m−3
Mr = 234.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 2976 reflections
a = 7.930 (2) Å	θ = 2.8–24.9°
b = 7.0256 (19) Å	µ = 3.88 mm−1
c = 14.499 (4) Å	T = 296 K
V = 807.8 (4) Å3	Block, colourless
Z = 4	0.32 × 0.25 × 0.21 mm
F(000) = 440

Bruker SMART APEXII CCD area-detector diffractometer	817 independent reflections
Radiation source: fine-focus sealed tube	739 reflections with I > 2σ(I)
graphite	Rint = 0.029
phi and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.370, Tmax = 0.496	k = −8→8
5541 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.259P] where P = (Fo2 + 2Fc2)/3
817 reflections	(Δ/σ)max = 0.001
57 parameters	Δρmax = 0.81 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 takeninto account individually in the estimation of esds in distances, anglesand torsion angles; correlations between esds in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4205 (6)	0.2500	0.4216 (3)	0.0559 (10)
C2	0.4224 (8)	0.2500	0.5763 (3)	0.0708 (13)
C3	0.5963 (8)	0.2500	0.5741 (3)	0.0746 (14)
H3	0.6587	0.2500	0.6285	0.090*
C4	0.6751 (7)	0.2500	0.4899 (3)	0.0680 (12)
C5	0.3278 (11)	0.2500	0.6665 (5)	0.108 (2)
H5A	0.2299	0.1703	0.6612	0.162*	0.50
H5B	0.2935	0.3775	0.6812	0.162*	0.50
H5C	0.3996	0.2022	0.7145	0.162*	0.50
C6	0.8651 (8)	0.2500	0.4820 (5)	0.107 (2)
H6A	0.9047	0.1215	0.4761	0.161*	0.50
H6B	0.9132	0.3068	0.5361	0.161*	0.50
H6C	0.8980	0.3218	0.4286	0.161*	0.50
I1	0.27885 (5)	0.2500	0.29859 (2)	0.07396 (18)
N1	0.3314 (6)	0.2500	0.4980 (2)	0.0656 (9)
N2	0.5862 (5)	0.2500	0.4101 (2)	0.0616 (9)

	U11	U22	U33	U12	U13	U23
C1	0.063 (3)	0.046 (2)	0.058 (2)	0.000	−0.002 (2)	0.000
C2	0.107 (4)	0.047 (2)	0.058 (3)	0.000	0.007 (3)	0.000
C3	0.106 (4)	0.059 (3)	0.059 (3)	0.000	−0.014 (3)	0.000
C4	0.076 (3)	0.064 (3)	0.064 (3)	0.000	−0.012 (2)	0.000
C5	0.158 (7)	0.098 (4)	0.068 (3)	0.000	0.022 (4)	0.000
C6	0.073 (4)	0.151 (6)	0.098 (4)	0.000	−0.014 (3)	0.000
I1	0.0685 (3)	0.0874 (3)	0.0660 (3)	0.000	−0.01043 (13)	0.000
N1	0.075 (2)	0.065 (2)	0.057 (2)	0.000	0.0106 (19)	0.000
N2	0.064 (2)	0.062 (2)	0.059 (2)	0.000	−0.0017 (17)	0.000

C1—N1	1.314 (6)	C4—N2	1.356 (6)
C1—N2	1.325 (6)	C4—C6	1.511 (9)
C1—I1	2.108 (4)	C5—H5A	0.9600
C2—N1	1.345 (7)	C5—H5B	0.9600
C2—C3	1.380 (9)	C5—H5C	0.9600
C2—C5	1.507 (8)	C6—H6A	0.9600
C3—C4	1.371 (7)	C6—H6B	0.9600
C3—H3	0.9300	C6—H6C	0.9600
N1—C1—N2	129.8 (4)	C2—C5—H5B	109.5
N1—C1—I1	115.3 (3)	H5A—C5—H5B	109.5
N2—C1—I1	114.9 (3)	C2—C5—H5C	109.5
N1—C2—C3	121.1 (5)	H5A—C5—H5C	109.5
N1—C2—C5	117.7 (6)	H5B—C5—H5C	109.5
C3—C2—C5	121.2 (6)	C4—C6—H6A	109.5
C4—C3—C2	118.4 (5)	C4—C6—H6B	109.5
C4—C3—H3	120.8	H6A—C6—H6B	109.5
C2—C3—H3	120.8	C4—C6—H6C	109.5
N2—C4—C3	121.6 (5)	H6A—C6—H6C	109.5
N2—C4—C6	116.9 (4)	H6B—C6—H6C	109.5
C3—C4—C6	121.5 (5)	C1—N1—C2	115.1 (5)
C2—C5—H5A	109.5	C1—N2—C4	114.1 (4)
N1—C2—C3—C4	0.0	C3—C2—N1—C1	0.0
C5—C2—C3—C4	180.0	C5—C2—N1—C1	180.0
C2—C3—C4—N2	0.0	N1—C1—N2—C4	0.0
C2—C3—C4—C6	180.0	I1—C1—N2—C4	180.0
N2—C1—N1—C2	0.0	C3—C4—N2—C1	0.00
I1—C1—N1—C2	180.0	C6—C4—N2—C1	180.0