2-(2-Meth­oxy­phen­oxy)pyrazine

Nasir, S.B.; Fairuz, Z.A.; Abdullah, Z.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811044321

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3088

doi:10.1107/S1600536811044321

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2-(2-Methoxyphenoxy)pyrazine

Shah Bakhtiar Nasir,^a Zainal Abidin Fairuz,^a Zanariah Abdullah,^a ‡ Seik Weng Ng ^a,^b and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 October 2011; accepted 25 October 2011; online 29 October 2011)

A significant twist is observed in the title molecule, C₁₁H₁₀N₂O₂, as seen in the dihedral angle between the pyrazine and benzene rings of 72.79 (8)°. The methoxy 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 interactions 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_r = 202.21
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.03
1743 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811044321/hg5121sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811044321/hg5121Isup3.cml

checkCIF report

Comment top

As a part of an on-going synthetic and structural study of N-heterocyclic derivatives (Aznan Akhmad et al., 2010), the title compound, (I), was investigated. In (I), Fig. 1, the benzene ring is almost orthogonal to the pyrazine ring, forming a dihedral angle of 72.79 (8)°. The methoxy substituent is co-planar to the benzene ring to which it is connected: the C11—O2—C10—C5 torsion angle is 175.83 (15)°. In the crystal structure, centrosymmetrically related pyrazine rings associate via weak π–π interactions [centroid···centroidⁱ distance = 3.8534 (10) Å for i: 1 - x, -y, 1 - z]. The dimeric aggregates stack along the b axis, Fig. 2.

Related literature top

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

Experimental top

o-Methoxyphenol (2.50 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) were dissolved in water (50 ml) and to the solution was added 2-chloropyrazine (2.28 g, 20 mmol) dissolved in THF (50 ml). The mixture was heated for 6 h. Water was added and the organic phase extracted with chloroform. The chloroform solution was dried over sodium sulfate; slow evaporation led to the formation of colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. Unit-cell contents for (I) shown in projection down the b axis. The π–π interactions are shown as purple dashed lines.

2-(2-Methoxyphenoxy)pyrazine top

Crystal data top

C₁₁H₁₀N₂O₂	F(000) = 424
M_r = 202.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.051P)² + 0.0981P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
1743 reflections	Δρ_max = 0.13 e Å⁻³
138 parameters	Δρ_min = −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)

Crystal data top

C₁₁H₁₀N₂O₂	V = 995.0 (2) Å³
M_r = 202.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7497 (10) Å	µ = 0.10 mm⁻¹
b = 5.8826 (8) Å	T = 293 K
c = 21.845 (3) Å	0.35 × 0.3 × 0.2 mm
β = 92.459 (2)°

Data collection top

Bruker SMART APEX diffractometer	1743 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1262 reflections with I > 2σ(I)
T_min = 0.789, T_max = 0.862	R_int = 0.041
7364 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
1743 reflections	Δρ_min = −0.13 e Å⁻³
138 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂O₂
M_r	202.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.7497 (10), 5.8826 (8), 21.845 (3)
β (°)	92.459 (2)
V (Å³)	995.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.3 × 0.2

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.789, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	7364, 1743, 1262
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.03
No. of reflections	1743
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.13

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Footnotes

‡Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

We thank the University of Malaya (grant No. RG027/09AFR) for supporting this study.

References

Aznan Akhmad, M. A., Abdullah, Z., Fairuz, Z. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2400. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
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