4,6-Dimethyl-2-p-tolyl-pyrimidine.

The mol-ecule of the title compound, C(13)H(14)N(2), is located on a crystallographic mirror plane. The aromatic rings make a dihedral angle of 3.4 (2)°. The H atoms of the methyl groups on the benzene ring are disordered over two positions; their site-occupation factors were fixed at 0.5. In the crystal, inter-molecular C-H⋯π contacts form infinite chains perpendicular to the b axis.

Related literature

The title compound was derived from the reaction of p-tolylmercutic chlorides and 4,6-dimethyl-2-iodopyrimidine. For general background to the use of organomercury compounds in cross-coupling reactions, see: Beletskaya et al. (2001 ▶); Braga et al. (2004 ▶). For a related structure, see: Santoni et al. (2008 ▶). For the synthesis, see: Xu et al. (2009a ▶,b ▶).

Experimental

Crystal data

C13H14N2

M = 198.26

Orthorhombic,

a = 7.2086 (10) Å

b = 12.4668 (18) Å

c = 12.4335 (18) Å

V = 1117.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.985

7934 measured reflections

1089 independent reflections

777 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.131

S = 1.06

1089 reflections

78 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904210X/si2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904210X/si2211Isup2.hkl

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

C13H14N2	Dx = 1.179 Mg m−3
Mr = 198.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 1634 reflections
a = 7.2086 (10) Å	θ = 2.3–23.3°
b = 12.4668 (18) Å	µ = 0.07 mm−1
c = 12.4335 (18) Å	T = 296 K
V = 1117.4 (3) Å3	Block, colourless
Z = 4	0.35 × 0.25 × 0.22 mm
F(000) = 424

Bruker SMART APEX CCD area-detector diffractometer	1089 independent reflections
Radiation source: fine-focus sealed tube	777 reflections with I > 2σ(I)
graphite	Rint = 0.025
phi and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.976, Tmax = 0.985	k = −15→15
7934 measured reflections	l = −15→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.291P] where P = (Fo2 + 2Fc2)/3
1089 reflections	(Δ/σ)max < 0.001
78 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.14 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

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	0.8988 (4)	0.2500	0.6728 (2)	0.0709 (8)
H1A	0.8781	0.2870	0.7394	0.106*	0.50
H1B	0.9952	0.2856	0.6332	0.106*	0.50
H1C	0.9355	0.1774	0.6874	0.106*	0.50
C2	0.7231 (3)	0.2500	0.60770 (17)	0.0499 (6)
C3	0.6383 (2)	0.34507 (13)	0.57708 (13)	0.0544 (5)
H3	0.6934	0.4100	0.5953	0.065*
C4	0.4741 (2)	0.34546 (12)	0.52012 (13)	0.0522 (5)
H4	0.4201	0.4105	0.5009	0.063*
C5	0.3884 (3)	0.2500	0.49107 (16)	0.0449 (5)
C6	0.2078 (3)	0.2500	0.43367 (17)	0.0468 (5)
C7	−0.0325 (2)	0.34504 (13)	0.36089 (13)	0.0529 (5)
C8	−0.1188 (3)	0.2500	0.33466 (18)	0.0549 (6)
H8	−0.2331	0.2500	0.3000	0.066*
C9	−0.1170 (3)	0.45227 (14)	0.33570 (16)	0.0732 (6)
H9A	−0.0974	0.5001	0.3951	0.110*
H9B	−0.2477	0.4438	0.3235	0.110*
H9C	−0.0598	0.4814	0.2724	0.110*
N1	0.13292 (18)	0.34589 (10)	0.41062 (10)	0.0509 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0703 (17)	0.0703 (18)	0.0720 (17)	0.000	−0.0169 (14)	0.000
C2	0.0541 (14)	0.0531 (13)	0.0425 (11)	0.000	−0.0007 (10)	0.000
C3	0.0600 (11)	0.0446 (9)	0.0584 (10)	−0.0043 (8)	−0.0036 (8)	−0.0048 (7)
C4	0.0588 (10)	0.0390 (9)	0.0589 (10)	0.0022 (7)	−0.0028 (8)	0.0002 (7)
C5	0.0507 (12)	0.0407 (11)	0.0433 (11)	0.000	0.0027 (10)	0.000
C6	0.0545 (13)	0.0430 (12)	0.0428 (11)	0.000	0.0018 (10)	0.000
C7	0.0550 (10)	0.0541 (10)	0.0496 (9)	0.0045 (8)	0.0009 (7)	0.0034 (7)
C8	0.0510 (13)	0.0608 (15)	0.0528 (13)	0.000	−0.0047 (11)	0.000
C9	0.0702 (12)	0.0598 (12)	0.0896 (14)	0.0091 (10)	−0.0128 (10)	0.0094 (10)
N1	0.0546 (8)	0.0449 (8)	0.0532 (8)	0.0031 (6)	−0.0025 (6)	0.0021 (6)

C1—C2	1.503 (3)	C5—C6	1.485 (3)
C1—H1A	0.9600	C6—N1i	1.3426 (16)
C1—H1B	0.9600	C6—N1	1.3426 (16)
C1—H1C	0.9600	C7—N1	1.343 (2)
C2—C3i	1.387 (2)	C7—C8	1.378 (2)
C2—C3	1.387 (2)	C7—C9	1.502 (2)
C3—C4	1.380 (2)	C8—C7i	1.378 (2)
C3—H3	0.9300	C8—H8	0.9300
C4—C5	1.3885 (19)	C9—H9A	0.9600
C4—H4	0.9300	C9—H9B	0.9600
C5—C4i	1.3885 (19)	C9—H9C	0.9600
C2—C1—H1A	109.5	C4i—C5—C6	121.00 (11)
C2—C1—H1B	109.5	N1i—C6—N1	125.8 (2)
H1A—C1—H1B	109.5	N1i—C6—C5	117.07 (10)
C2—C1—H1C	109.5	N1—C6—C5	117.07 (10)
H1A—C1—H1C	109.5	N1—C7—C8	121.12 (16)
H1B—C1—H1C	109.5	N1—C7—C9	116.67 (15)
C3i—C2—C3	117.4 (2)	C8—C7—C9	122.20 (16)
C3i—C2—C1	121.28 (11)	C7—C8—C7i	118.7 (2)
C3—C2—C1	121.28 (11)	C7—C8—H8	120.7
C4—C3—C2	121.48 (16)	C7i—C8—H8	120.7
C4—C3—H3	119.3	C7—C9—H9A	109.5
C2—C3—H3	119.3	C7—C9—H9B	109.5
C3—C4—C5	120.81 (16)	H9A—C9—H9B	109.5
C3—C4—H4	119.6	C7—C9—H9C	109.5
C5—C4—H4	119.6	H9A—C9—H9C	109.5
C4—C5—C4i	118.0 (2)	H9B—C9—H9C	109.5
C4—C5—C6	121.00 (11)	C6—N1—C7	116.62 (15)
C3i—C2—C3—C4	1.2 (3)	C4i—C5—C6—N1	178.65 (17)
C1—C2—C3—C4	−178.02 (19)	N1—C7—C8—C7i	0.3 (3)
C2—C3—C4—C5	−0.3 (3)	C9—C7—C8—C7i	−179.77 (14)
C3—C4—C5—C4i	−0.7 (3)	N1i—C6—N1—C7	0.6 (3)
C3—C4—C5—C6	177.47 (16)	C5—C6—N1—C7	−178.53 (15)
C4—C5—C6—N1i	−178.65 (17)	C8—C7—N1—C6	−0.4 (3)
C4i—C5—C6—N1i	−0.6 (3)	C9—C7—N1—C6	179.62 (16)
C4—C5—C6—N1	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ii	0.93	2.79	3.638 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg1i	0.93	2.79	3.638 (2)	152

Symmetry code: (i) . Cg1 is the centroid of the pyrimidine ring.