2-(1H-Imidazol-1-yl)-4,6-dimethyl-pyrimidine.

The asymmetric unit of the title compound, C(9)H(10)N(4), consists of two mol-ecules in which the dihedral angles between the planes of the imidazole and pyrimidine rings are 4.8 (1) and 2.1 (1)°.

Related literature

For related pyrimidine derivatives, see: Wu et al. (2008 ▶); Cetina et al. (2005 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C9H10N4

M = 174.21

Monoclinic,

a = 9.304 (5) Å

b = 26.756 (5) Å

c = 7.129 (5) Å

β = 91.259 (5)°

V = 1774.2 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART diffractometer

11971 measured reflections

3091 independent reflections

2365 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.197

S = 1.14

3091 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044357/ng5247sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044357/ng5247Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044357/ng5247Isup3.cml

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

C9H10N4	F(000) = 736
Mr = 174.21	Dx = 1.304 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3786 reflections
a = 9.304 (5) Å	θ = 2.7–25.4°
b = 26.756 (5) Å	µ = 0.09 mm−1
c = 7.129 (5) Å	T = 296 K
β = 91.259 (5)°	Needle, white
V = 1774.2 (16) Å3	0.20 × 0.10 × 0.10 mm
Z = 8

Bruker SMART diffractometer	2365 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.040
graphite	θmax = 25.0°, θmin = 1.5°
ω scans	h = −11→10
11971 measured reflections	k = −26→31
3091 independent reflections	l = −8→8

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)] = 0.064	H-atom parameters constrained
wR(F2) = 0.197	w = 1/[σ2(Fo2) + (0.0895P)2 + 0.9302P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
3091 reflections	Δρmax = 0.25 e Å−3
240 parameters	Δρmin = −0.19 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: 0.008 (2)

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.

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.

	x	y	z	Uiso*/Ueq
N7	0.3875 (2)	0.45208 (8)	0.7788 (3)	0.0472 (6)
N2	0.1912 (2)	0.21267 (8)	0.6762 (3)	0.0493 (6)
N4	−0.0469 (2)	0.22566 (9)	0.5881 (3)	0.0483 (6)
N8	0.5461 (2)	0.52131 (8)	0.7336 (3)	0.0461 (6)
N6	0.3095 (2)	0.53376 (8)	0.8162 (3)	0.0465 (6)
C13	0.4215 (3)	0.50025 (10)	0.7736 (4)	0.0420 (6)
C14	0.4946 (3)	0.42061 (10)	0.7404 (4)	0.0471 (7)
N3	0.1114 (2)	0.29410 (9)	0.6535 (3)	0.0513 (6)
C15	0.6291 (3)	0.43849 (11)	0.6982 (4)	0.0517 (7)
H15	0.7034	0.4164	0.6727	0.062*
C4	0.0780 (3)	0.24630 (10)	0.6363 (4)	0.0453 (7)
N5	0.0973 (3)	0.56080 (10)	0.9067 (4)	0.0649 (8)
C5	0.0032 (3)	0.32600 (11)	0.6131 (4)	0.0539 (8)
C16	0.6525 (3)	0.48921 (11)	0.6942 (4)	0.0474 (7)
C7	−0.1541 (3)	0.25785 (11)	0.5495 (4)	0.0494 (7)
C6	−0.1306 (3)	0.30860 (11)	0.5581 (4)	0.0550 (8)
H6	−0.2041	0.3309	0.5271	0.066*
C10	0.1743 (3)	0.52165 (12)	0.8750 (4)	0.0552 (8)
H10	0.1420	0.4890	0.8903	0.066*
N1	0.4063 (3)	0.18529 (10)	0.7662 (5)	0.0728 (9)
C11	0.3144 (3)	0.58522 (11)	0.8102 (4)	0.0548 (8)
H11	0.3914	0.6051	0.7755	0.066*
C9	−0.2980 (3)	0.23589 (13)	0.4997 (5)	0.0647 (9)
H9A	−0.2873	0.2114	0.4027	0.097*
H9B	−0.3615	0.2619	0.4560	0.097*
H9C	−0.3373	0.2203	0.6086	0.097*
C3	0.3271 (3)	0.22439 (12)	0.7368 (5)	0.0622 (9)
H3	0.3593	0.2570	0.7551	0.075*
C18	0.7944 (3)	0.51142 (13)	0.6463 (5)	0.0625 (9)
H18A	0.7812	0.5352	0.5464	0.094*
H18B	0.8582	0.4854	0.6070	0.094*
H18C	0.8351	0.5279	0.7546	0.094*
C17	0.4608 (4)	0.36581 (11)	0.7441 (5)	0.0664 (9)
H17A	0.3708	0.3607	0.8044	0.100*
H17B	0.5356	0.3484	0.8123	0.100*
H17C	0.4545	0.3533	0.6180	0.100*
C1	0.1867 (3)	0.16122 (11)	0.6687 (5)	0.0629 (9)
H1	0.1088	0.1413	0.6328	0.076*
C12	0.1844 (3)	0.60062 (12)	0.8651 (5)	0.0647 (9)
H12	0.1569	0.6339	0.8738	0.078*
C8	0.0358 (4)	0.38062 (12)	0.6319 (6)	0.0768 (11)
H8A	0.0052	0.3923	0.7520	0.115*
H8B	−0.0143	0.3987	0.5344	0.115*
H8C	0.1374	0.3859	0.6214	0.115*
C2	0.3180 (3)	0.14584 (13)	0.7239 (6)	0.0734 (10)
H2	0.3456	0.1125	0.7323	0.088*

	U11	U22	U33	U12	U13	U23
N7	0.0400 (13)	0.0420 (13)	0.0596 (14)	−0.0005 (10)	−0.0030 (10)	−0.0009 (10)
N2	0.0380 (13)	0.0443 (14)	0.0659 (15)	−0.0011 (10)	0.0068 (11)	0.0059 (11)
N4	0.0401 (13)	0.0492 (14)	0.0559 (14)	−0.0035 (10)	0.0065 (10)	0.0015 (10)
N8	0.0342 (12)	0.0457 (14)	0.0583 (14)	−0.0013 (10)	−0.0026 (10)	−0.0007 (10)
N6	0.0354 (12)	0.0439 (13)	0.0601 (14)	0.0023 (10)	−0.0018 (10)	−0.0037 (10)
C13	0.0358 (14)	0.0414 (15)	0.0485 (15)	0.0028 (11)	−0.0041 (11)	−0.0017 (11)
C14	0.0433 (15)	0.0424 (15)	0.0553 (16)	0.0035 (12)	−0.0057 (12)	−0.0024 (12)
N3	0.0425 (13)	0.0436 (14)	0.0681 (15)	−0.0002 (11)	0.0125 (11)	0.0031 (11)
C15	0.0395 (15)	0.0509 (18)	0.0645 (18)	0.0094 (13)	−0.0011 (13)	−0.0025 (13)
C4	0.0387 (15)	0.0454 (16)	0.0522 (16)	0.0021 (12)	0.0109 (12)	0.0040 (12)
N5	0.0360 (13)	0.0625 (17)	0.096 (2)	0.0053 (12)	0.0027 (13)	−0.0125 (14)
C5	0.0479 (17)	0.0472 (17)	0.0672 (18)	0.0042 (13)	0.0165 (14)	0.0047 (13)
C16	0.0366 (14)	0.0505 (17)	0.0548 (17)	0.0018 (12)	−0.0038 (12)	0.0009 (12)
C7	0.0404 (15)	0.0578 (18)	0.0504 (16)	0.0026 (13)	0.0092 (12)	0.0050 (13)
C6	0.0411 (16)	0.0547 (19)	0.0694 (19)	0.0047 (13)	0.0094 (14)	0.0074 (14)
C10	0.0357 (15)	0.0547 (18)	0.075 (2)	−0.0004 (13)	0.0035 (13)	−0.0041 (14)
N1	0.0422 (15)	0.0608 (18)	0.115 (2)	0.0029 (13)	0.0018 (15)	0.0157 (16)
C11	0.0427 (16)	0.0431 (16)	0.078 (2)	0.0040 (13)	0.0000 (14)	−0.0005 (14)
C9	0.0428 (17)	0.081 (2)	0.071 (2)	−0.0022 (16)	0.0011 (14)	−0.0004 (17)
C3	0.0402 (17)	0.0538 (19)	0.093 (2)	−0.0027 (14)	−0.0002 (15)	0.0081 (16)
C18	0.0376 (16)	0.064 (2)	0.086 (2)	0.0005 (14)	0.0039 (15)	0.0028 (16)
C17	0.0557 (19)	0.0439 (18)	0.100 (2)	−0.0009 (15)	0.0019 (17)	−0.0026 (16)
C1	0.0459 (17)	0.0442 (17)	0.099 (2)	−0.0030 (14)	0.0063 (16)	0.0055 (16)
C12	0.0490 (18)	0.0501 (19)	0.095 (2)	0.0104 (15)	−0.0030 (16)	−0.0094 (16)
C8	0.060 (2)	0.0479 (19)	0.124 (3)	0.0022 (16)	0.015 (2)	0.0013 (19)
C2	0.0458 (18)	0.0491 (19)	0.126 (3)	0.0060 (15)	0.0120 (18)	0.0158 (19)

N7—C13	1.328 (3)	C7—C9	1.497 (4)
N7—C14	1.337 (4)	C6—H6	0.9300
N2—C3	1.363 (4)	C10—H10	0.9300
N2—C1	1.378 (4)	N1—C3	1.294 (4)
N2—C4	1.410 (4)	N1—C2	1.367 (4)
N4—C4	1.325 (4)	C11—C12	1.344 (4)
N4—C7	1.342 (4)	C11—H11	0.9300
N8—C13	1.326 (3)	C9—H9A	0.9600
N8—C16	1.345 (3)	C9—H9B	0.9600
N6—C10	1.373 (4)	C9—H9C	0.9600
N6—C11	1.379 (4)	C3—H3	0.9300
N6—C13	1.413 (3)	C18—H18A	0.9600
C14—C15	1.379 (4)	C18—H18B	0.9600
C14—C17	1.500 (4)	C18—H18C	0.9600
N3—C4	1.321 (4)	C17—H17A	0.9600
N3—C5	1.347 (4)	C17—H17B	0.9600
C15—C16	1.375 (4)	C17—H17C	0.9600
C15—H15	0.9300	C1—C2	1.340 (5)
N5—C10	1.292 (4)	C1—H1	0.9300
N5—C12	1.375 (4)	C12—H12	0.9300
C5—C6	1.378 (4)	C8—H8A	0.9600
C5—C8	1.498 (4)	C8—H8B	0.9600
C16—C18	1.495 (4)	C8—H8C	0.9600
C7—C6	1.377 (4)	C2—H2	0.9300
C13—N7—C14	115.3 (2)	C12—C11—N6	105.5 (3)
C3—N2—C1	105.6 (2)	C12—C11—H11	127.3
C3—N2—C4	126.9 (3)	N6—C11—H11	127.3
C1—N2—C4	127.4 (2)	C7—C9—H9A	109.5
C4—N4—C7	115.4 (2)	C7—C9—H9B	109.5
C13—N8—C16	115.1 (2)	H9A—C9—H9B	109.5
C10—N6—C11	106.0 (2)	C7—C9—H9C	109.5
C10—N6—C13	126.9 (2)	H9A—C9—H9C	109.5
C11—N6—C13	127.0 (2)	H9B—C9—H9C	109.5
N8—C13—N7	128.9 (2)	N1—C3—N2	112.7 (3)
N8—C13—N6	115.4 (2)	N1—C3—H3	123.6
N7—C13—N6	115.6 (2)	N2—C3—H3	123.6
N7—C14—C15	120.7 (3)	C16—C18—H18A	109.5
N7—C14—C17	117.0 (3)	C16—C18—H18B	109.5
C15—C14—C17	122.3 (3)	H18A—C18—H18B	109.5
C4—N3—C5	114.8 (3)	C16—C18—H18C	109.5
C16—C15—C14	119.5 (3)	H18A—C18—H18C	109.5
C16—C15—H15	120.3	H18B—C18—H18C	109.5
C14—C15—H15	120.3	C14—C17—H17A	109.5
N3—C4—N4	129.1 (3)	C14—C17—H17B	109.5
N3—C4—N2	115.2 (2)	H17A—C17—H17B	109.5
N4—C4—N2	115.7 (2)	C14—C17—H17C	109.5
C10—N5—C12	105.0 (3)	H17A—C17—H17C	109.5
N3—C5—C6	120.9 (3)	H17B—C17—H17C	109.5
N3—C5—C8	116.8 (3)	C2—C1—N2	105.5 (3)
C6—C5—C8	122.4 (3)	C2—C1—H1	127.2
N8—C16—C15	120.6 (2)	N2—C1—H1	127.2
N8—C16—C18	116.9 (2)	C11—C12—N5	111.3 (3)
C15—C16—C18	122.6 (3)	C11—C12—H12	124.3
N4—C7—C6	120.5 (3)	N5—C12—H12	124.3
N4—C7—C9	116.9 (3)	C5—C8—H8A	109.5
C6—C7—C9	122.6 (3)	C5—C8—H8B	109.5
C7—C6—C5	119.2 (3)	H8A—C8—H8B	109.5
C7—C6—H6	120.4	C5—C8—H8C	109.5
C5—C6—H6	120.4	H8A—C8—H8C	109.5
N5—C10—N6	112.2 (3)	H8B—C8—H8C	109.5
N5—C10—H10	123.9	C1—C2—N1	111.6 (3)
N6—C10—H10	123.9	C1—C2—H2	124.2
C3—N1—C2	104.5 (3)	N1—C2—H2	124.2
C16—N8—C13—N7	−0.5 (4)	C13—N8—C16—C18	179.4 (3)
C16—N8—C13—N6	179.7 (2)	C14—C15—C16—N8	0.9 (4)
C14—N7—C13—N8	0.9 (4)	C14—C15—C16—C18	−178.9 (3)
C14—N7—C13—N6	−179.3 (2)	C4—N4—C7—C6	1.0 (4)
C10—N6—C13—N8	−175.0 (3)	C4—N4—C7—C9	−178.3 (2)
C11—N6—C13—N8	3.8 (4)	N4—C7—C6—C5	−2.2 (4)
C10—N6—C13—N7	5.2 (4)	C9—C7—C6—C5	177.1 (3)
C11—N6—C13—N7	−176.0 (3)	N3—C5—C6—C7	1.7 (4)
C13—N7—C14—C15	−0.3 (4)	C8—C5—C6—C7	−178.0 (3)
C13—N7—C14—C17	−179.9 (3)	C12—N5—C10—N6	0.7 (4)
N7—C14—C15—C16	−0.6 (4)	C11—N6—C10—N5	−0.5 (4)
C17—C14—C15—C16	179.0 (3)	C13—N6—C10—N5	178.5 (3)
C5—N3—C4—N4	−1.2 (4)	C10—N6—C11—C12	0.1 (3)
C5—N3—C4—N2	179.3 (2)	C13—N6—C11—C12	−178.9 (3)
C7—N4—C4—N3	0.8 (4)	C2—N1—C3—N2	−0.3 (4)
C7—N4—C4—N2	−179.7 (2)	C1—N2—C3—N1	0.3 (4)
C3—N2—C4—N3	2.8 (4)	C4—N2—C3—N1	178.3 (3)
C1—N2—C4—N3	−179.7 (3)	C3—N2—C1—C2	−0.2 (4)
C3—N2—C4—N4	−176.8 (3)	C4—N2—C1—C2	−178.1 (3)
C1—N2—C4—N4	0.8 (4)	N6—C11—C12—N5	0.3 (4)
C4—N3—C5—C6	−0.1 (4)	C10—N5—C12—C11	−0.6 (4)
C4—N3—C5—C8	179.6 (3)	N2—C1—C2—N1	0.0 (4)
C13—N8—C16—C15	−0.4 (4)	C3—N1—C2—C1	0.2 (4)