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

A significant twist is observed in the title molecule, C(11)H(10)N(2)O(2), as seen in the dihedral angle between the pyrazine and benzene rings of 72.79 (8)°. The meth-oxy group is almost coplanar with the benzene ring to which it is attached [C-O-C-C torsion angle = 175.83 (15)°]. Centrosymmetric dimers are formed in the crystal structure which are held together by weak π-π inter-actions between pyrazine rings [centroid-centroid distance = 3.8534 (10) Å].

Related literature

For the structure of a related pyrimidine derivative, see: Aznan Akhmad et al. (2010 ▶).

Experimental

Crystal data

C11H10N2O2

M = 202.21

Monoclinic,

a = 7.7497 (10) Å

b = 5.8826 (8) Å

c = 21.845 (3) Å

β = 92.459 (2)°

V = 995.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.3 × 0.2 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.789, T max = 0.862

7364 measured reflections

1743 independent reflections

1262 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.03

1743 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 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 datablock(s) global, I. DOI: 10.1107/S1600536811044321/hg5121sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044321/hg5121Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044321/hg5121Isup3.cml

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

C11H10N2O2	F(000) = 424
Mr = 202.21	Dx = 1.350 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1739 reflections
a = 7.7497 (10) Å	θ = 2.8–27.3°
b = 5.8826 (8) Å	µ = 0.10 mm−1
c = 21.845 (3) Å	T = 293 K
β = 92.459 (2)°	Block, colourless
V = 995.0 (2) Å3	0.35 × 0.3 × 0.2 mm
Z = 4

Bruker SMART APEX diffractometer	1743 independent reflections
Radiation source: fine-focus sealed tube	1262 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.789, Tmax = 0.862	k = −6→6
7364 measured reflections	l = −25→25

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.051P)2 + 0.0981P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1743 reflections	Δρmax = 0.13 e Å−3
138 parameters	Δρmin = −0.13 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: 0.105 (7)

	x	y	z	Uiso*/Ueq
O1	0.44004 (16)	0.13299 (17)	0.62993 (5)	0.0618 (4)
O2	0.56589 (16)	0.4818 (2)	0.69804 (6)	0.0658 (4)
N1	0.58582 (17)	0.3536 (2)	0.56159 (6)	0.0505 (4)
N2	0.7704 (2)	−0.0324 (2)	0.53106 (8)	0.0716 (5)
C1	0.5605 (2)	0.1567 (2)	0.58683 (7)	0.0455 (4)
C2	0.6494 (2)	−0.0375 (3)	0.57169 (8)	0.0626 (5)
H2	0.6235	−0.1744	0.5905	0.075*
C3	0.7991 (2)	0.1687 (3)	0.50551 (9)	0.0609 (5)
H3	0.8842	0.1806	0.4770	0.073*
C4	0.7080 (2)	0.3568 (3)	0.51984 (8)	0.0535 (5)
H4	0.7310	0.4928	0.5001	0.064*
C5	0.3345 (2)	0.3184 (3)	0.64234 (7)	0.0487 (4)
C6	0.1658 (3)	0.3139 (3)	0.62125 (8)	0.0637 (5)
H6	0.1254	0.1940	0.5969	0.076*
C7	0.0555 (2)	0.4879 (4)	0.63627 (9)	0.0711 (6)
H7	−0.0593	0.4862	0.6219	0.085*
C8	0.1162 (3)	0.6618 (3)	0.67224 (9)	0.0674 (6)
H8	0.0420	0.7789	0.6824	0.081*
C9	0.2854 (2)	0.6670 (3)	0.69370 (8)	0.0571 (5)
H9	0.3249	0.7873	0.7181	0.068*
C10	0.3965 (2)	0.4947 (3)	0.67918 (7)	0.0484 (4)
C11	0.6363 (3)	0.6667 (3)	0.73229 (10)	0.0794 (6)
H11A	0.7582	0.6441	0.7394	0.119*
H11B	0.5817	0.6761	0.7708	0.119*
H11C	0.6166	0.8052	0.7098	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0810 (9)	0.0387 (6)	0.0682 (8)	0.0039 (5)	0.0331 (7)	0.0021 (5)
O2	0.0604 (8)	0.0644 (8)	0.0725 (8)	0.0036 (6)	0.0023 (6)	−0.0089 (6)
N1	0.0558 (9)	0.0438 (8)	0.0529 (8)	0.0063 (6)	0.0124 (7)	0.0032 (6)
N2	0.0788 (12)	0.0533 (9)	0.0851 (11)	0.0142 (8)	0.0294 (9)	−0.0049 (8)
C1	0.0516 (10)	0.0403 (9)	0.0450 (9)	0.0003 (7)	0.0088 (7)	−0.0039 (7)
C2	0.0779 (13)	0.0399 (9)	0.0716 (12)	0.0082 (8)	0.0209 (10)	0.0004 (8)
C3	0.0575 (11)	0.0613 (11)	0.0655 (11)	0.0062 (9)	0.0200 (9)	−0.0036 (9)
C4	0.0531 (10)	0.0532 (10)	0.0551 (10)	0.0039 (8)	0.0130 (8)	0.0054 (8)
C5	0.0584 (11)	0.0415 (9)	0.0479 (9)	0.0004 (8)	0.0209 (8)	0.0017 (7)
C6	0.0681 (13)	0.0671 (12)	0.0569 (11)	−0.0133 (10)	0.0153 (9)	−0.0117 (9)
C7	0.0531 (12)	0.0906 (15)	0.0703 (12)	0.0018 (10)	0.0112 (9)	−0.0025 (12)
C8	0.0642 (13)	0.0642 (12)	0.0758 (13)	0.0118 (10)	0.0244 (10)	−0.0003 (10)
C9	0.0637 (12)	0.0478 (10)	0.0612 (11)	−0.0007 (8)	0.0204 (9)	−0.0056 (8)
C10	0.0539 (10)	0.0449 (9)	0.0476 (9)	−0.0006 (8)	0.0153 (7)	0.0024 (7)
C11	0.0816 (15)	0.0739 (14)	0.0819 (14)	−0.0131 (11)	−0.0062 (11)	−0.0045 (11)

O1—C1	1.3611 (18)	C5—C6	1.368 (2)
O1—C5	1.3969 (18)	C5—C10	1.386 (2)
O2—C10	1.361 (2)	C6—C7	1.382 (3)
O2—C11	1.416 (2)	C6—H6	0.9300
N1—C1	1.3013 (19)	C7—C8	1.362 (3)
N1—C4	1.343 (2)	C7—H7	0.9300
N2—C2	1.319 (2)	C8—C9	1.374 (3)
N2—C3	1.331 (2)	C8—H8	0.9300
C1—C2	1.382 (2)	C9—C10	1.376 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.356 (2)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C1—O1—C5	118.61 (11)	C5—C6—H6	120.1
C10—O2—C11	117.50 (14)	C7—C6—H6	120.1
C1—N1—C4	115.09 (13)	C8—C7—C6	119.45 (19)
C2—N2—C3	116.06 (14)	C8—C7—H7	120.3
N1—C1—O1	120.31 (13)	C6—C7—H7	120.3
N1—C1—C2	123.27 (14)	C7—C8—C9	120.97 (17)
O1—C1—C2	116.42 (14)	C7—C8—H8	119.5
N2—C2—C1	121.24 (16)	C9—C8—H8	119.5
N2—C2—H2	119.4	C8—C9—C10	120.18 (17)
C1—C2—H2	119.4	C8—C9—H9	119.9
N2—C3—C4	122.03 (16)	C10—C9—H9	119.9
N2—C3—H3	119.0	O2—C10—C9	125.19 (16)
C4—C3—H3	119.0	O2—C10—C5	116.11 (14)
N1—C4—C3	122.29 (15)	C9—C10—C5	118.71 (17)
N1—C4—H4	118.9	O2—C11—H11A	109.5
C3—C4—H4	118.9	O2—C11—H11B	109.5
C6—C5—C10	120.86 (15)	H11A—C11—H11B	109.5
C6—C5—O1	118.58 (15)	O2—C11—H11C	109.5
C10—C5—O1	120.38 (16)	H11A—C11—H11C	109.5
C5—C6—C7	119.83 (17)	H11B—C11—H11C	109.5
C4—N1—C1—O1	179.84 (14)	O1—C5—C6—C7	175.72 (14)
C4—N1—C1—C2	−1.0 (2)	C5—C6—C7—C8	−0.3 (3)
C5—O1—C1—N1	5.6 (2)	C6—C7—C8—C9	0.1 (3)
C5—O1—C1—C2	−173.59 (15)	C7—C8—C9—C10	−0.2 (3)
C3—N2—C2—C1	−0.7 (3)	C11—O2—C10—C9	−4.0 (2)
N1—C1—C2—N2	1.7 (3)	C11—O2—C10—C5	175.83 (15)
O1—C1—C2—N2	−179.10 (16)	C8—C9—C10—O2	−179.69 (16)
C2—N2—C3—C4	−0.8 (3)	C8—C9—C10—C5	0.5 (2)
C1—N1—C4—C3	−0.5 (3)	C6—C5—C10—O2	179.48 (14)
N2—C3—C4—N1	1.5 (3)	O1—C5—C10—O2	4.4 (2)
C1—O1—C5—C6	106.12 (17)	C6—C5—C10—C9	−0.7 (2)
C1—O1—C5—C10	−78.74 (19)	O1—C5—C10—C9	−175.73 (13)
C10—C5—C6—C7	0.6 (3)