2-(3-Meth-oxy-phen-oxy)pyrimidine.

In the title compound, C(11)H(10)N(2)O(2), the benzene ring faces towards one of the pyrimidine N atoms, and is almost orthogonal to the plane through the pyrimidine ring [dihedral angle = 84.40 (14)°]. In the crystal, the presence of C-H⋯π and π-π [centroid-centroid separation = 3.7658 (18) Å] inter-actions leads to a supra-molecular array in the ac plane. The layers thus formed inter-digitate along the b axis.

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶).

Experimental

Crystal data

C11H10N2O2

M = 202.21

Monoclinic,

a = 8.8120 (16) Å

b = 18.215 (3) Å

c = 7.2094 (10) Å

β = 119.380 (2)°

V = 1008.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.30 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.889, T max = 1.000

4725 measured reflections

1165 independent reflections

897 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.02

1165 reflections

138 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.10 e Å−3

Absolute structure: nd

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003014X/hb5584sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003014X/hb5584Isup2.hkl

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

C11H10N2O2	F(000) = 424
Mr = 202.21	Dx = 1.332 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1361 reflections
a = 8.8120 (16) Å	θ = 2.2–21.9°
b = 18.215 (3) Å	µ = 0.09 mm−1
c = 7.2094 (10) Å	T = 293 K
β = 119.380 (2)°	Prism, colourless
V = 1008.4 (3) Å3	0.40 × 0.30 × 0.08 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1165 independent reflections
Radiation source: fine-focus sealed tube	897 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.889, Tmax = 1.000	k = −23→23
4725 measured reflections	l = −9→9

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.0614P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.10 e Å−3
1165 reflections	Δρmin = −0.10 e Å−3
138 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: nd
Secondary atom site location: difference Fourier map

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
O1	0.5000 (2)	0.02433 (8)	0.5000 (3)	0.0629 (5)
O2	0.7604 (2)	0.21319 (8)	0.3071 (3)	0.0628 (5)
N1	0.2553 (3)	0.09456 (10)	0.4018 (3)	0.0595 (5)
N2	0.2520 (3)	−0.03621 (10)	0.4056 (4)	0.0655 (6)
C1	0.3265 (3)	0.02912 (11)	0.4325 (4)	0.0510 (5)
C2	0.0840 (4)	0.09409 (16)	0.3359 (5)	0.0756 (8)
H2	0.0262	0.1387	0.3129	0.091*
C3	−0.0084 (4)	0.03096 (19)	0.3015 (5)	0.0828 (9)
H3	−0.1272	0.0314	0.2555	0.099*
C4	0.0819 (4)	−0.03306 (17)	0.3379 (5)	0.0789 (8)
H4	0.0213	−0.0770	0.3141	0.095*
C5	0.5948 (3)	0.09030 (11)	0.5548 (4)	0.0531 (6)
C6	0.6335 (3)	0.12134 (10)	0.4098 (4)	0.0484 (5)
H6	0.5954	0.0995	0.2776	0.058*
C7	0.7304 (3)	0.18570 (11)	0.4623 (3)	0.0488 (5)
C8	0.7882 (3)	0.21731 (13)	0.6603 (4)	0.0624 (6)
H8	0.8527	0.2605	0.6970	0.075*
C9	0.7481 (4)	0.18335 (17)	0.8027 (4)	0.0771 (8)
H9	0.7870	0.2045	0.9359	0.093*
C10	0.6533 (3)	0.11978 (16)	0.7543 (4)	0.0697 (7)
H10	0.6292	0.0973	0.8529	0.084*
C11	0.8382 (4)	0.28395 (15)	0.3411 (5)	0.0868 (9)
H11A	0.8443	0.2986	0.2169	0.130*
H11B	0.9535	0.2823	0.4615	0.130*
H11C	0.7692	0.3187	0.3676	0.130*

	U11	U22	U33	U12	U13	U23
O1	0.0614 (11)	0.0435 (8)	0.0919 (13)	0.0088 (7)	0.0438 (11)	0.0096 (8)
O2	0.0722 (11)	0.0520 (9)	0.0643 (10)	−0.0123 (8)	0.0335 (8)	−0.0019 (8)
N1	0.0551 (11)	0.0530 (11)	0.0691 (12)	0.0075 (9)	0.0294 (10)	−0.0016 (10)
N2	0.0773 (15)	0.0501 (12)	0.0735 (14)	−0.0070 (10)	0.0403 (12)	−0.0005 (10)
C1	0.0553 (14)	0.0481 (12)	0.0565 (14)	0.0034 (10)	0.0329 (12)	0.0045 (10)
C2	0.0570 (16)	0.0763 (17)	0.087 (2)	0.0111 (14)	0.0299 (15)	−0.0078 (15)
C3	0.0562 (17)	0.101 (2)	0.087 (2)	−0.0074 (16)	0.0322 (15)	−0.0199 (17)
C4	0.076 (2)	0.0799 (19)	0.084 (2)	−0.0262 (17)	0.0412 (16)	−0.0136 (15)
C5	0.0468 (12)	0.0451 (12)	0.0666 (14)	0.0094 (9)	0.0273 (11)	0.0057 (10)
C6	0.0480 (12)	0.0415 (10)	0.0535 (12)	0.0036 (9)	0.0231 (10)	−0.0013 (9)
C7	0.0427 (11)	0.0464 (10)	0.0546 (13)	0.0040 (9)	0.0219 (10)	0.0008 (10)
C8	0.0555 (13)	0.0619 (13)	0.0614 (15)	−0.0069 (11)	0.0223 (12)	−0.0156 (12)
C9	0.0779 (19)	0.097 (2)	0.0549 (15)	−0.0069 (16)	0.0315 (14)	−0.0186 (15)
C10	0.0733 (17)	0.0811 (18)	0.0651 (17)	0.0059 (14)	0.0419 (14)	0.0032 (14)
C11	0.103 (2)	0.0589 (16)	0.088 (2)	−0.0223 (14)	0.0389 (19)	0.0037 (14)

O1—C1	1.361 (3)	C5—C6	1.372 (3)
O1—C5	1.405 (3)	C5—C10	1.377 (3)
O2—C7	1.365 (3)	C6—C7	1.389 (3)
O2—C11	1.424 (3)	C6—H6	0.9300
N1—C1	1.314 (3)	C7—C8	1.384 (3)
N1—C2	1.342 (3)	C8—C9	1.384 (4)
N2—C1	1.327 (3)	C8—H8	0.9300
N2—C4	1.330 (4)	C9—C10	1.369 (4)
C2—C3	1.360 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.363 (4)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C1—O1—C5	117.01 (16)	C5—C6—H6	120.3
C7—O2—C11	117.50 (19)	C7—C6—H6	120.3
C1—N1—C2	114.5 (2)	O2—C7—C8	124.9 (2)
C1—N2—C4	113.7 (2)	O2—C7—C6	115.23 (18)
N1—C1—N2	128.9 (2)	C8—C7—C6	119.9 (2)
N1—C1—O1	118.57 (19)	C7—C8—C9	118.7 (2)
N2—C1—O1	112.54 (19)	C7—C8—H8	120.7
N1—C2—C3	122.6 (3)	C9—C8—H8	120.7
N1—C2—H2	118.7	C10—C9—C8	122.4 (3)
C3—C2—H2	118.7	C10—C9—H9	118.8
C2—C3—C4	116.6 (3)	C8—C9—H9	118.8
C2—C3—H3	121.7	C9—C10—C5	117.7 (2)
C4—C3—H3	121.7	C9—C10—H10	121.2
N2—C4—C3	123.6 (3)	C5—C10—H10	121.2
N2—C4—H4	118.2	O2—C11—H11A	109.5
C3—C4—H4	118.2	O2—C11—H11B	109.5
C6—C5—C10	122.0 (2)	H11A—C11—H11B	109.5
C6—C5—O1	118.3 (2)	O2—C11—H11C	109.5
C10—C5—O1	119.6 (2)	H11A—C11—H11C	109.5
C5—C6—C7	119.3 (2)	H11B—C11—H11C	109.5
C2—N1—C1—N2	0.6 (4)	C10—C5—C6—C7	−2.0 (3)
C2—N1—C1—O1	−179.8 (2)	O1—C5—C6—C7	−178.59 (19)
C4—N2—C1—N1	0.1 (4)	C11—O2—C7—C8	−8.0 (3)
C4—N2—C1—O1	−179.5 (2)	C11—O2—C7—C6	171.7 (2)
C5—O1—C1—N1	6.9 (3)	C5—C6—C7—O2	−179.02 (19)
C5—O1—C1—N2	−173.5 (2)	C5—C6—C7—C8	0.7 (3)
C1—N1—C2—C3	−0.7 (4)	O2—C7—C8—C9	180.0 (2)
N1—C2—C3—C4	0.2 (5)	C6—C7—C8—C9	0.3 (3)
C1—N2—C4—C3	−0.8 (4)	C7—C8—C9—C10	−0.1 (4)
C2—C3—C4—N2	0.6 (5)	C8—C9—C10—C5	−1.1 (4)
C1—O1—C5—C6	−100.4 (2)	C6—C5—C10—C9	2.1 (4)
C1—O1—C5—C10	82.8 (3)	O1—C5—C10—C9	178.7 (2)

Cg2 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2i	0.93	2.89	3.710 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg2i	0.93	2.89	3.710 (4)	148

Symmetry code: (i) .