Crystal structure of 4,6-di-chloro-5-methyl-pyrimidine.

The title compound, C5H4Cl2N2, is essentially planar with an r.m.s. deviation for all non-H atoms of 0.009 Å. The largest deviation from the mean plane is 0.016 (4) Å for an N atom. In the crystal, mol-ecules are linked by pairs of C-H⋯N hydrogen bonds, forming inversion dimers, enclosing an R (2) 2(6) ring motif.

Related literature

For the applications of pyrimidine derivatives as pesticides and pharmaceutical agents, see: Condon et al. (1993 ▸); as agrochemicals, see: Maeno et al. (1990 ▸); as anti­viral agents, see: Gilchrist (1997 ▸); as herbicides, see: Selby et al. (2002 ▸); Zhu et al. (2007 ▸); and for applications of organoselenide compounds, see: Ip et al. (1997 ▸). For the crystal structure of 5-methyl­pyrimidine, see: Furberg et al. (1979 ▸).

Experimental

Crystal data

C5H4Cl2N2

M = 163.00

Monoclinic,

a = 7.463 (5) Å

b = 7.827 (5) Å

c = 11.790 (5) Å

β = 93.233 (5)°

V = 687.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.85 mm−1

T = 293 K

0.11 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013 ▸) T min = 0.922, T max = 0.934

2347 measured reflections

1228 independent reflections

791 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.173

S = 1.01

1228 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2013 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014/6 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015024020/su5261sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024020/su5261Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015024020/su5261fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015024020/su5261fig2.tif

The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines (see Table 1).

CCDC reference: 1442378

Additional supporting information: crystallographic information; 3D view; checkCIF report

C5H4Cl2N2	F(000) = 328
Mr = 163.00	Dx = 1.575 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.463 (5) Å	Cell parameters from 776 reflections
b = 7.827 (5) Å	θ = 4.2–27.8°
c = 11.790 (5) Å	µ = 0.85 mm−1
β = 93.233 (5)°	T = 293 K
V = 687.6 (7) Å3	Prism, colourless
Z = 4	0.11 × 0.10 × 0.08 mm

Oxford Diffraction Xcalibur, Eos diffractometer	1228 independent reflections
Radiation source: Enhance (Mo) X-ray Source	791 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
CCD rotation images, thin slices ω scans	θmax = 25.2°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013)	h = −8→8
Tmin = 0.922, Tmax = 0.934	k = −9→4
2347 measured reflections	l = −14→10

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3
1228 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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

	x	y	z	Uiso*/Ueq
Cl14	0.47393 (16)	0.21816 (17)	0.57181 (8)	0.0686 (5)
Cl16	0.45631 (17)	0.4430 (2)	0.13763 (9)	0.0853 (6)
N1	0.2066 (5)	0.4832 (6)	0.2775 (3)	0.0604 (11)
N3	0.2153 (5)	0.3882 (5)	0.4695 (3)	0.0579 (10)
C2	0.1383 (6)	0.4657 (7)	0.3784 (4)	0.0661 (14)
H2	0.0251	0.5123	0.3865	0.079*
C4	0.3744 (5)	0.3225 (5)	0.4544 (3)	0.0458 (10)
C5	0.4659 (5)	0.3309 (6)	0.3546 (3)	0.0458 (10)
C6	0.3650 (6)	0.4175 (6)	0.2685 (3)	0.0514 (11)
C51	0.6464 (6)	0.2553 (7)	0.3426 (4)	0.0666 (14)
H51A	0.7041	0.3121	0.2823	0.100*
H51B	0.6344	0.1359	0.3252	0.100*
H51C	0.7175	0.2692	0.4124	0.100*

	U11	U22	U33	U12	U13	U23
Cl14	0.0846 (9)	0.0601 (9)	0.0604 (6)	−0.0009 (7)	−0.0019 (6)	0.0089 (5)
Cl16	0.0934 (11)	0.1053 (14)	0.0592 (7)	−0.0109 (9)	0.0219 (6)	0.0116 (6)
N1	0.057 (2)	0.061 (3)	0.063 (2)	0.005 (2)	0.0033 (16)	0.0012 (19)
N3	0.057 (2)	0.057 (3)	0.0602 (19)	0.000 (2)	0.0160 (15)	−0.0040 (17)
C2	0.050 (2)	0.074 (4)	0.075 (3)	0.008 (3)	0.005 (2)	−0.008 (3)
C4	0.045 (2)	0.039 (3)	0.0537 (19)	−0.003 (2)	0.0041 (16)	−0.0034 (18)
C5	0.042 (2)	0.039 (3)	0.057 (2)	−0.005 (2)	0.0089 (16)	−0.0056 (17)
C6	0.054 (2)	0.053 (3)	0.0475 (18)	−0.004 (2)	0.0070 (16)	−0.0023 (18)
C51	0.051 (3)	0.070 (4)	0.081 (3)	0.007 (3)	0.016 (2)	−0.002 (2)

Cl14—C4	1.737 (4)	C4—C5	1.395 (5)
Cl16—C6	1.733 (4)	C5—C6	1.403 (6)
N1—C6	1.299 (6)	C5—C51	1.486 (6)
N1—C2	1.327 (5)	C51—H51A	0.9600
N3—C4	1.315 (5)	C51—H51B	0.9600
N3—C2	1.335 (5)	C51—H51C	0.9600
C2—H2	0.9300
C6—N1—C2	115.4 (3)	C6—C5—C51	125.2 (4)
C4—N3—C2	114.8 (3)	N1—C6—C5	125.9 (3)
N1—C2—N3	126.8 (4)	N1—C6—Cl16	115.6 (3)
N1—C2—H2	116.6	C5—C6—Cl16	118.5 (3)
N3—C2—H2	116.6	C5—C51—H51A	109.5
N3—C4—C5	125.7 (4)	C5—C51—H51B	109.5
N3—C4—Cl14	115.1 (3)	H51A—C51—H51B	109.5
C5—C4—Cl14	119.2 (3)	C5—C51—H51C	109.5
C4—C5—C6	111.4 (4)	H51A—C51—H51C	109.5
C4—C5—C51	123.4 (4)	H51B—C51—H51C	109.5
C6—N1—C2—N3	−0.2 (8)	Cl14—C4—C5—C51	−0.2 (6)
C4—N3—C2—N1	−0.7 (8)	C2—N1—C6—C5	0.5 (8)
C2—N3—C4—C5	1.3 (7)	C2—N1—C6—Cl16	−179.0 (4)
C2—N3—C4—Cl14	−178.9 (4)	C4—C5—C6—N1	0.1 (7)
N3—C4—C5—C6	−1.1 (6)	C51—C5—C6—N1	179.5 (5)
Cl14—C4—C5—C6	179.2 (3)	C4—C5—C6—Cl16	179.6 (3)
N3—C4—C5—C51	179.5 (4)	C51—C5—C6—Cl16	−1.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N3i	0.93	2.66	3.468 (6)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N3i	0.93	2.66	3.468 (6)	146

Symmetry code: (i) .