2-(4-Meth-oxy-phen-oxy)pyrazine.

In the title compound, C(11)H(10)N(2)O(2), the aromatic rings are almost orthogonal to each other [dihedral angle = 86.97 (8)°], with the benzene ring orientated to face one of the pyrazine N atoms. In the crystal, centrosymmetrically related pairs are connected via pairs of C-H⋯π inter-actions and the dimeric units thus formed pack into undulating layers that stack along the a axis.

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C11H10N2O2

M = 202.21

Monoclinic,

a = 5.8783 (2) Å

b = 10.9298 (4) Å

c = 15.6430 (6) Å

β = 97.109 (2)°

V = 997.32 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

5515 measured reflections

1743 independent reflections

1244 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.05

1743 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

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/S1600536810031946/hb5602sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031946/hb5602Isup2.hkl

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

C11H10N2O2	F(000) = 424
Mr = 202.21	Dx = 1.347 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1293 reflections
a = 5.8783 (2) Å	θ = 2.3–22.4°
b = 10.9298 (4) Å	µ = 0.10 mm−1
c = 15.6430 (6) Å	T = 293 K
β = 97.109 (2)°	Block, colourless
V = 997.32 (6) Å3	0.35 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1244 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 25.0°, θmin = 2.3°
ω scans	h = −6→6
5515 measured reflections	k = −12→12
1743 independent reflections	l = −18→18

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.0504P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1743 reflections	Δρmax = 0.13 e Å−3
138 parameters	Δρmin = −0.12 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: 0.042 (4)

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	0.80138 (19)	0.41576 (11)	0.38163 (8)	0.0650 (4)
O2	0.0132 (2)	0.59432 (11)	0.19506 (8)	0.0638 (4)
N1	0.6059 (2)	0.26379 (12)	0.44535 (9)	0.0494 (4)
N2	1.0286 (2)	0.18218 (14)	0.52555 (9)	0.0599 (4)
C1	0.7989 (3)	0.31704 (15)	0.43404 (10)	0.0442 (4)
C2	1.0109 (3)	0.27760 (17)	0.47408 (11)	0.0544 (5)
H2	1.1426	0.3197	0.4642	0.065*
C3	0.8320 (3)	0.12604 (17)	0.53716 (12)	0.0579 (5)
H3	0.8364	0.0578	0.5729	0.069*
C4	0.6268 (3)	0.16632 (15)	0.49808 (12)	0.0559 (5)
H4	0.4948	0.1247	0.5082	0.067*
C5	0.5920 (3)	0.45725 (15)	0.33748 (11)	0.0489 (4)
C6	0.5262 (3)	0.41868 (15)	0.25481 (12)	0.0548 (5)
H6	0.6122	0.3603	0.2299	0.066*
C7	0.3328 (3)	0.46665 (16)	0.20906 (11)	0.0554 (5)
H7	0.2881	0.4407	0.1529	0.066*
C8	0.2035 (3)	0.55333 (14)	0.24574 (10)	0.0458 (4)
C9	0.2718 (3)	0.59135 (15)	0.32910 (11)	0.0516 (5)
H9	0.1863	0.6494	0.3547	0.062*
C10	0.4674 (3)	0.54303 (16)	0.37434 (10)	0.0548 (5)
H10	0.5145	0.5692	0.4303	0.066*
C11	−0.1195 (3)	0.68815 (16)	0.22838 (12)	0.0637 (5)
H11A	−0.2509	0.7059	0.1875	0.096*
H11B	−0.0278	0.7606	0.2386	0.096*
H11C	−0.1691	0.6611	0.2815	0.096*

	U11	U22	U33	U12	U13	U23
O1	0.0391 (7)	0.0747 (9)	0.0790 (9)	−0.0056 (6)	−0.0008 (6)	0.0292 (7)
O2	0.0585 (8)	0.0683 (8)	0.0606 (8)	0.0168 (6)	−0.0080 (6)	−0.0020 (6)
N1	0.0386 (8)	0.0495 (8)	0.0588 (9)	0.0018 (6)	0.0009 (6)	0.0061 (7)
N2	0.0492 (9)	0.0715 (10)	0.0566 (9)	0.0120 (8)	−0.0032 (7)	0.0042 (8)
C1	0.0373 (9)	0.0497 (10)	0.0447 (9)	0.0013 (7)	0.0010 (7)	0.0008 (8)
C2	0.0382 (10)	0.0698 (12)	0.0539 (10)	0.0005 (8)	0.0003 (8)	−0.0011 (10)
C3	0.0598 (12)	0.0538 (11)	0.0584 (11)	0.0097 (9)	0.0007 (9)	0.0081 (9)
C4	0.0482 (11)	0.0502 (10)	0.0682 (12)	0.0001 (8)	0.0035 (9)	0.0089 (9)
C5	0.0404 (10)	0.0500 (10)	0.0553 (10)	−0.0039 (8)	0.0028 (8)	0.0146 (9)
C6	0.0483 (11)	0.0525 (11)	0.0641 (11)	0.0066 (8)	0.0086 (9)	−0.0053 (9)
C7	0.0571 (12)	0.0596 (11)	0.0484 (10)	0.0020 (9)	0.0018 (8)	−0.0104 (9)
C8	0.0450 (10)	0.0440 (9)	0.0476 (9)	−0.0007 (7)	0.0026 (8)	0.0036 (8)
C9	0.0553 (11)	0.0511 (10)	0.0490 (10)	0.0072 (8)	0.0082 (8)	−0.0028 (8)
C10	0.0591 (11)	0.0640 (11)	0.0401 (9)	−0.0019 (9)	0.0017 (8)	−0.0008 (9)
C11	0.0519 (11)	0.0621 (11)	0.0772 (13)	0.0109 (9)	0.0088 (10)	0.0112 (10)

O1—C1	1.3563 (19)	C5—C10	1.361 (2)
O1—C5	1.4096 (19)	C5—C6	1.370 (2)
O2—C8	1.3639 (18)	C6—C7	1.371 (2)
O2—C11	1.426 (2)	C6—H6	0.9300
N1—C1	1.3062 (19)	C7—C8	1.383 (2)
N1—C4	1.344 (2)	C7—H7	0.9300
N2—C2	1.314 (2)	C8—C9	1.380 (2)
N2—C3	1.341 (2)	C9—C10	1.378 (2)
C1—C2	1.392 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.357 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C1—O1—C5	118.56 (12)	C5—C6—H6	120.2
C8—O2—C11	118.05 (13)	C7—C6—H6	120.2
C1—N1—C4	114.95 (14)	C6—C7—C8	120.56 (16)
C2—N2—C3	116.22 (15)	C6—C7—H7	119.7
N1—C1—O1	120.72 (14)	C8—C7—H7	119.7
N1—C1—C2	123.03 (16)	O2—C8—C9	124.90 (15)
O1—C1—C2	116.26 (14)	O2—C8—C7	115.92 (15)
N2—C2—C1	121.37 (16)	C9—C8—C7	119.17 (16)
N2—C2—H2	119.3	C10—C9—C8	119.77 (15)
C1—C2—H2	119.3	C10—C9—H9	120.1
N2—C3—C4	121.60 (17)	C8—C9—H9	120.1
N2—C3—H3	119.2	C5—C10—C9	120.31 (16)
C4—C3—H3	119.2	C5—C10—H10	119.8
N1—C4—C3	122.83 (16)	C9—C10—H10	119.8
N1—C4—H4	118.6	O2—C11—H11A	109.5
C3—C4—H4	118.6	O2—C11—H11B	109.5
C10—C5—C6	120.54 (16)	H11A—C11—H11B	109.5
C10—C5—O1	119.79 (16)	O2—C11—H11C	109.5
C6—C5—O1	119.42 (16)	H11A—C11—H11C	109.5
C5—C6—C7	119.64 (16)	H11B—C11—H11C	109.5
C4—N1—C1—O1	179.38 (14)	C10—C5—C6—C7	−0.2 (3)
C4—N1—C1—C2	−0.8 (2)	O1—C5—C6—C7	−174.50 (14)
C5—O1—C1—N1	−2.0 (2)	C5—C6—C7—C8	−0.2 (3)
C5—O1—C1—C2	178.13 (14)	C11—O2—C8—C9	3.5 (2)
C3—N2—C2—C1	−0.2 (2)	C11—O2—C8—C7	−176.93 (14)
N1—C1—C2—N2	0.8 (3)	C6—C7—C8—O2	−179.41 (15)
O1—C1—C2—N2	−179.37 (15)	C6—C7—C8—C9	0.2 (3)
C2—N2—C3—C4	−0.3 (3)	O2—C8—C9—C10	179.76 (15)
C1—N1—C4—C3	0.3 (2)	C7—C8—C9—C10	0.2 (2)
N2—C3—C4—N1	0.3 (3)	C6—C5—C10—C9	0.6 (3)
C1—O1—C5—C10	90.59 (19)	O1—C5—C10—C9	174.88 (14)
C1—O1—C5—C6	−95.10 (18)	C8—C9—C10—C5	−0.6 (3)

Cg1 is the centroid of the N1,N2,C1–C4 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1i	0.93	2.87	3.6326 (18)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,N2,C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg1i	0.93	2.87	3.6326 (18)	140

Symmetry code: (i) .