2-[3-Meth-oxy-5-(pyrimidin-2-yl)phen-yl]pyrimidine.

The title compound, C15H12N4O, was synthesized by a standard Suzuki cross-coupling reaction. The terminal pyrim-idine rings are rotated at dihedral angles of 12.06 (4) and -13.13 (4)° with respect to the central benzene ring. In the crystal, the mol-ecules are connected by two kinds of C-H⋯N hydrogen bonds, forming zigzag chains along the c axis. Weak π-π inter-actions between the benzene and one of the pyrimidine rings are also found and stack the mol-ecules along the b axis [centroid-centroid distance = 4.112 (3) Å].

Related literature

For general background to the chemistry of tridentate NCN ligands, see: Pugh & Danopoulos (2007 ▶); Wu et al. (2009 ▶, 2012 ▶); Williams (2009 ▶); Wang et al. (2010 ▶). For the synthesis of the title compound, see: Avitia et al. (2011 ▶); Wakioka et al. (2010 ▶); Cardenas & Echavarren (1999 ▶).

Experimental

Crystal data

C15H12N4O

M = 264.29

Orthorhombic,

a = 11.3779 (8) Å

b = 8.0954 (6) Å

c = 27.3371 (18) Å

V = 2518.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.28 × 0.21 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.800, T max = 1.000

14088 measured reflections

2461 independent reflections

2059 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.04

2461 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002663/sj5297sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002663/sj5297Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002663/sj5297Isup3.cml

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

C15H12N4O	F(000) = 1104
Mr = 264.29	Dx = 1.394 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4404 reflections
a = 11.3779 (8) Å	θ = 4.7–56.5°
b = 8.0954 (6) Å	µ = 0.09 mm−1
c = 27.3371 (18) Å	T = 293 K
V = 2518.0 (3) Å3	Prismatic, colourless
Z = 8	0.28 × 0.21 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	2461 independent reflections
Radiation source: fine-focus sealed tube	2059 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→12
Tmin = 0.800, Tmax = 1.000	k = −8→9
14088 measured reflections	l = −33→31

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.4657P] where P = (Fo2 + 2Fc2)/3
2461 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 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.

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
N1	1.03793 (11)	0.23473 (17)	0.28017 (4)	0.0556 (4)
N2	1.20879 (9)	0.20037 (16)	0.32842 (4)	0.0508 (3)
N3	0.65549 (10)	−0.04972 (17)	0.43132 (4)	0.0550 (3)
N4	0.65653 (10)	0.05619 (16)	0.35048 (4)	0.0519 (3)
O1	1.07030 (9)	−0.16817 (14)	0.46649 (3)	0.0572 (3)
C1	1.02113 (12)	−0.07963 (17)	0.42928 (4)	0.0434 (3)
C2	0.89954 (12)	−0.07835 (17)	0.42817 (5)	0.0444 (3)
H2	0.8574	−0.1340	0.4522	0.053*
C3	0.84023 (11)	0.00505 (16)	0.39159 (4)	0.0394 (3)
C4	0.90336 (11)	0.08851 (16)	0.35561 (4)	0.0387 (3)
H4	0.8639	0.1440	0.3308	0.046*
C5	1.02519 (11)	0.08866 (16)	0.35693 (4)	0.0380 (3)
C6	1.08424 (11)	0.00412 (16)	0.39390 (4)	0.0415 (3)
H6	1.1660	0.0040	0.3948	0.050*
C7	1.09451 (11)	0.17957 (16)	0.31955 (4)	0.0392 (3)
C8	1.10177 (14)	0.3194 (2)	0.24815 (6)	0.0609 (4)
H8	1.0644	0.3616	0.2206	0.073*
C9	1.21922 (13)	0.3476 (2)	0.25355 (6)	0.0554 (4)
H9	1.2626	0.4064	0.2306	0.067*
C10	1.26891 (12)	0.2841 (2)	0.29482 (6)	0.0567 (4)
H10	1.3490	0.3001	0.2998	0.068*
C11	0.70953 (11)	0.00467 (17)	0.39113 (4)	0.0417 (3)
C12	0.53848 (13)	−0.0495 (2)	0.43016 (6)	0.0627 (5)
H12	0.4977	−0.0875	0.4574	0.075*
C13	0.47587 (13)	0.0040 (2)	0.39070 (6)	0.0609 (4)
H13	0.3941	0.0056	0.3907	0.073*
C14	0.53930 (13)	0.0549 (2)	0.35126 (6)	0.0589 (4)
H14	0.4991	0.0905	0.3236	0.071*
C15	1.19460 (14)	−0.1760 (2)	0.46883 (6)	0.0639 (5)
H15A	1.2246	−0.2221	0.4390	0.096*
H15B	1.2177	−0.2443	0.4959	0.096*
H15C	1.2258	−0.0668	0.4732	0.096*

	U11	U22	U33	U12	U13	U23
N1	0.0475 (6)	0.0735 (9)	0.0457 (6)	−0.0099 (6)	−0.0043 (5)	0.0165 (6)
N2	0.0395 (6)	0.0582 (8)	0.0548 (7)	−0.0046 (5)	−0.0003 (5)	0.0092 (6)
N3	0.0450 (7)	0.0736 (9)	0.0466 (7)	−0.0109 (6)	0.0072 (5)	−0.0010 (6)
N4	0.0403 (6)	0.0610 (8)	0.0542 (7)	0.0031 (5)	0.0002 (5)	0.0046 (6)
O1	0.0531 (6)	0.0696 (7)	0.0491 (6)	0.0027 (5)	−0.0065 (4)	0.0201 (5)
C1	0.0468 (7)	0.0460 (8)	0.0375 (6)	0.0020 (6)	−0.0027 (5)	0.0030 (6)
C2	0.0463 (8)	0.0490 (8)	0.0378 (6)	−0.0033 (6)	0.0050 (5)	0.0046 (6)
C3	0.0387 (7)	0.0411 (7)	0.0383 (6)	−0.0012 (5)	0.0021 (5)	−0.0037 (5)
C4	0.0395 (7)	0.0415 (7)	0.0352 (6)	0.0008 (5)	−0.0013 (5)	0.0001 (5)
C5	0.0387 (7)	0.0395 (7)	0.0357 (6)	−0.0010 (5)	0.0012 (5)	−0.0027 (5)
C6	0.0359 (6)	0.0472 (8)	0.0414 (7)	0.0001 (5)	−0.0014 (5)	−0.0003 (6)
C7	0.0380 (6)	0.0410 (7)	0.0385 (6)	−0.0010 (5)	0.0006 (5)	−0.0021 (5)
C8	0.0611 (9)	0.0768 (11)	0.0449 (8)	−0.0123 (8)	−0.0027 (7)	0.0170 (8)
C9	0.0587 (9)	0.0581 (9)	0.0495 (8)	−0.0128 (7)	0.0122 (6)	0.0053 (7)
C10	0.0397 (7)	0.0626 (10)	0.0677 (10)	−0.0083 (7)	0.0078 (6)	0.0072 (8)
C11	0.0400 (7)	0.0425 (7)	0.0426 (7)	−0.0017 (5)	0.0036 (5)	−0.0050 (6)
C12	0.0465 (8)	0.0834 (12)	0.0582 (9)	−0.0140 (8)	0.0140 (7)	−0.0097 (8)
C13	0.0356 (7)	0.0702 (11)	0.0768 (11)	−0.0021 (7)	0.0063 (7)	−0.0170 (9)
C14	0.0416 (8)	0.0652 (10)	0.0699 (10)	0.0051 (7)	−0.0055 (7)	−0.0001 (8)
C15	0.0553 (9)	0.0735 (11)	0.0628 (9)	0.0086 (8)	−0.0128 (7)	0.0178 (8)

N1—C8	1.3280 (18)	C4—H4	0.9300
N1—C7	1.3316 (17)	C5—C6	1.3934 (17)
N2—C10	1.3310 (18)	C5—C7	1.4859 (17)
N2—C7	1.3333 (16)	C6—H6	0.9300
N3—C12	1.3317 (19)	C8—C9	1.364 (2)
N3—C11	1.3338 (16)	C8—H8	0.9300
N4—C11	1.3311 (17)	C9—C10	1.363 (2)
N4—C14	1.3340 (18)	C9—H9	0.9300
O1—C1	1.3643 (15)	C10—H10	0.9300
O1—C15	1.4171 (18)	C12—C13	1.363 (2)
C1—C6	1.3821 (18)	C12—H12	0.9300
C1—C2	1.3838 (18)	C13—C14	1.361 (2)
C2—C3	1.3826 (18)	C13—H13	0.9300
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.3928 (17)	C15—H15A	0.9600
C3—C11	1.4872 (18)	C15—H15B	0.9600
C4—C5	1.3867 (17)	C15—H15C	0.9600
C8—N1—C7	116.21 (12)	N1—C8—H8	118.3
C10—N2—C7	116.10 (12)	C9—C8—H8	118.3
C12—N3—C11	116.16 (13)	C10—C9—C8	115.66 (13)
C11—N4—C14	115.93 (12)	C10—C9—H9	122.2
C1—O1—C15	117.79 (11)	C8—C9—H9	122.2
O1—C1—C6	124.49 (12)	N2—C10—C9	123.39 (13)
O1—C1—C2	115.47 (11)	N2—C10—H10	118.3
C6—C1—C2	120.03 (11)	C9—C10—H10	118.3
C3—C2—C1	120.49 (12)	N4—C11—N3	125.60 (12)
C3—C2—H2	119.8	N4—C11—C3	117.35 (11)
C1—C2—H2	119.8	N3—C11—C3	117.04 (11)
C2—C3—C4	119.74 (12)	N3—C12—C13	122.78 (14)
C2—C3—C11	119.55 (11)	N3—C12—H12	118.6
C4—C3—C11	120.71 (11)	C13—C12—H12	118.6
C5—C4—C3	119.83 (11)	C14—C13—C12	116.48 (14)
C5—C4—H4	120.1	C14—C13—H13	121.8
C3—C4—H4	120.1	C12—C13—H13	121.8
C4—C5—C6	120.04 (11)	N4—C14—C13	123.02 (15)
C4—C5—C7	120.87 (11)	N4—C14—H14	118.5
C6—C5—C7	119.09 (11)	C13—C14—H14	118.5
C1—C6—C5	119.87 (12)	O1—C15—H15A	109.5
C1—C6—H6	120.1	O1—C15—H15B	109.5
C5—C6—H6	120.1	H15A—C15—H15B	109.5
N1—C7—N2	125.18 (12)	O1—C15—H15C	109.5
N1—C7—C5	117.74 (11)	H15A—C15—H15C	109.5
N2—C7—C5	117.07 (11)	H15B—C15—H15C	109.5
N1—C8—C9	123.44 (14)
C15—O1—C1—C6	−0.5 (2)	C6—C5—C7—N1	168.58 (12)
C15—O1—C1—C2	178.92 (13)	C4—C5—C7—N2	167.50 (12)
O1—C1—C2—C3	−178.88 (12)	C6—C5—C7—N2	−11.89 (18)
C6—C1—C2—C3	0.6 (2)	C7—N1—C8—C9	1.4 (2)
C1—C2—C3—C4	−0.05 (19)	N1—C8—C9—C10	−0.6 (3)
C1—C2—C3—C11	179.97 (12)	C7—N2—C10—C9	0.5 (2)
C2—C3—C4—C5	−0.56 (18)	C8—C9—C10—N2	−0.4 (2)
C11—C3—C4—C5	179.41 (11)	C14—N4—C11—N3	1.3 (2)
C3—C4—C5—C6	0.63 (18)	C14—N4—C11—C3	−179.78 (13)
C3—C4—C5—C7	−178.76 (11)	C12—N3—C11—N4	−0.9 (2)
O1—C1—C6—C5	178.91 (12)	C12—N3—C11—C3	−179.84 (13)
C2—C1—C6—C5	−0.52 (19)	C2—C3—C11—N4	−166.49 (13)
C4—C5—C6—C1	−0.10 (18)	C4—C3—C11—N4	13.54 (18)
C7—C5—C6—C1	179.31 (12)	C2—C3—C11—N3	12.55 (18)
C8—N1—C7—N2	−1.3 (2)	C4—C3—C11—N3	−167.43 (12)
C8—N1—C7—C5	178.20 (13)	C11—N3—C12—C13	−0.5 (2)
C10—N2—C7—N1	0.4 (2)	N3—C12—C13—C14	1.4 (3)
C10—N2—C7—C5	−179.09 (13)	C11—N4—C14—C13	−0.2 (2)
C4—C5—C7—N1	−12.03 (18)	C12—C13—C14—N4	−1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N4i	0.93	2.69	3.597 (2)	166
C15—H15B···N3ii	0.96	2.69	3.547 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N4i	0.93	2.69	3.597 (2)	166
C15—H15B⋯N3ii	0.96	2.69	3.547 (2)	149

Symmetry codes: (i) ; (ii) .