Phenyl pyrazin-2-yl ether

Abstract

In the title compound, C₁₀H₈N₂O, the dihedral angle between the aromatic rings is 64.2 (1)° and the bridging C—O—C angle is 119.1 (1)°.

Related literature

For the structure of quinoxalinyl phenyl ether, see: Hassan et al. (2008 ▶). For the structure of N-(pyrazin-2-yl)aniline, see: Wan Saffiee et al. (2008 ▶).

Experimental

Crystal data

• C₁₀H₈N₂O

• M _r = 172.18

• Monoclinic,

• a = 5.704 (1) Å

• b = 8.557 (2) Å

• c = 17.595 (4) Å

• β = 94.382 (3)°

• V = 856.4 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 100 (2) K

• 0.20 × 0.15 × 0.10 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: none

• 4641 measured reflections

• 1950 independent reflections

• 1207 reflections with I > 2σ(I)

• R _int = 0.042

Refinement

• R[F ² > 2σ(F ²)] = 0.046

• wR(F ²) = 0.119

• S = 0.97

• 1950 reflections

• 118 parameters

• H-atom parameters constrained

• Δρ_max = 0.20 e Å⁻³

• Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

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

supplementary crystallographic information

Experimental

Phenol (0.94 g, 0.01 mol) was dissolved in a small volume of water containing sodium hydroxide (0.40 g, 0.01 mol). The mixture was heated to remove most of the water. This and 2-chloropyrazine (1.15 g, 0.01 mol) were heated for 5 h. The material was extracted with chloroform and the organic phase then dried over sodium sulfate. Evaporation of the solvent gave the crude product, which was recrystallized from chloroform.

Refinement

The H atoms were placed in calculated positions (C—H = 0.95 Å) and refined as riding with U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H8N2O	F(000) = 360
Mr = 172.18	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 739 reflections
a = 5.704 (1) Å	θ = 3.3–26.1°
b = 8.557 (2) Å	µ = 0.09 mm−1
c = 17.595 (4) Å	T = 100 K
β = 94.382 (3)°	Irregular block, colorless
V = 856.4 (3) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	1207 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 27.5°, θmin = 2.3°
ω scans	h = −6→7
4641 measured reflections	k = −11→10
1950 independent reflections	l = −22→21

Refinement

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3
1950 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0900 (2)	0.70888 (14)	0.45704 (7)	0.0301 (3)
N1	0.4770 (3)	0.56153 (17)	0.60955 (8)	0.0281 (4)
N2	0.4352 (3)	0.81790 (16)	0.51088 (8)	0.0252 (4)
C1	0.0879 (3)	0.8138 (2)	0.39557 (9)	0.0244 (4)
C2	−0.1015 (3)	0.9128 (2)	0.38509 (10)	0.0288 (4)
H2	−0.2208	0.9130	0.4199	0.035*
C3	−0.1150 (3)	1.0127 (2)	0.32238 (10)	0.0320 (5)
H3	−0.2447	1.0819	0.3140	0.038*
C4	0.0604 (3)	1.0112 (2)	0.27248 (10)	0.0309 (5)
H4	0.0520	1.0803	0.2301	0.037*
C5	0.2481 (3)	0.9097 (2)	0.28386 (10)	0.0298 (5)
H5	0.3672	0.9086	0.2489	0.036*
C6	0.2641 (3)	0.8093 (2)	0.34580 (9)	0.0266 (4)
H6	0.3927	0.7393	0.3539	0.032*
C7	0.2816 (3)	0.70451 (19)	0.50838 (9)	0.0225 (4)
C8	0.2987 (3)	0.5762 (2)	0.55764 (10)	0.0279 (4)
H8	0.1799	0.4981	0.5537	0.033*
C9	0.6367 (3)	0.6767 (2)	0.61232 (10)	0.0275 (4)
H9	0.7686	0.6707	0.6486	0.033*
C10	0.6149 (3)	0.8027 (2)	0.56430 (9)	0.0274 (4)
H10	0.7311	0.8823	0.5690	0.033*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0285 (7)	0.0309 (8)	0.0299 (7)	−0.0092 (6)	−0.0033 (5)	0.0105 (6)
N1	0.0356 (9)	0.0253 (8)	0.0237 (8)	−0.0023 (7)	0.0037 (7)	0.0021 (7)
N2	0.0304 (9)	0.0229 (8)	0.0222 (8)	−0.0055 (6)	0.0020 (6)	0.0000 (7)
C1	0.0279 (10)	0.0230 (10)	0.0215 (9)	−0.0088 (8)	−0.0028 (7)	0.0039 (8)
C2	0.0233 (10)	0.0323 (11)	0.0307 (10)	−0.0049 (8)	0.0021 (7)	0.0031 (9)
C3	0.0267 (11)	0.0321 (11)	0.0362 (10)	−0.0007 (8)	−0.0041 (8)	0.0044 (9)
C4	0.0338 (11)	0.0344 (11)	0.0237 (9)	−0.0062 (9)	−0.0037 (8)	0.0068 (9)
C5	0.0316 (11)	0.0368 (11)	0.0209 (9)	−0.0056 (9)	0.0011 (8)	−0.0027 (9)
C6	0.0280 (10)	0.0256 (10)	0.0255 (9)	−0.0014 (8)	−0.0020 (8)	−0.0032 (8)
C7	0.0253 (10)	0.0224 (10)	0.0203 (8)	−0.0029 (7)	0.0043 (7)	−0.0007 (8)
C8	0.0319 (11)	0.0246 (10)	0.0274 (10)	−0.0060 (8)	0.0048 (8)	0.0015 (8)
C9	0.0315 (11)	0.0287 (10)	0.0219 (9)	−0.0001 (8)	−0.0011 (7)	0.0005 (8)
C10	0.0295 (10)	0.0287 (11)	0.0238 (9)	−0.0076 (8)	0.0003 (7)	−0.0011 (9)

Geometric parameters (Å, °)

O1—C7	1.364 (2)	C3—H3	0.9500
O1—C1	1.4050 (19)	C4—C5	1.382 (3)
N1—C8	1.320 (2)	C4—H4	0.9500
N1—C9	1.340 (2)	C5—C6	1.385 (2)
N2—C7	1.306 (2)	C5—H5	0.9500
N2—C10	1.343 (2)	C6—H6	0.9500
C1—C2	1.374 (3)	C7—C8	1.398 (2)
C1—C6	1.383 (2)	C8—H8	0.9500
C2—C3	1.394 (2)	C9—C10	1.370 (2)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.381 (3)	C10—H10	0.9500
C7—O1—C1	119.11 (13)	C6—C5—H5	119.8
C8—N1—C9	116.18 (15)	C1—C6—C5	118.29 (17)
C7—N2—C10	115.21 (15)	C1—C6—H6	120.9
C2—C1—C6	122.28 (16)	C5—C6—H6	120.9
C2—C1—O1	117.23 (15)	N2—C7—O1	120.23 (15)
C6—C1—O1	120.38 (16)	N2—C7—C8	123.24 (16)
C1—C2—C3	118.68 (17)	O1—C7—C8	116.52 (15)
C1—C2—H2	120.7	N1—C8—C7	121.13 (16)
C3—C2—H2	120.7	N1—C8—H8	119.4
C4—C3—C2	119.90 (18)	C7—C8—H8	119.4
C4—C3—H3	120.0	N1—C9—C10	121.80 (16)
C2—C3—H3	120.0	N1—C9—H9	119.1
C3—C4—C5	120.36 (17)	C10—C9—H9	119.1
C3—C4—H4	119.8	N2—C10—C9	122.43 (17)
C5—C4—H4	119.8	N2—C10—H10	118.8
C4—C5—C6	120.49 (17)	C9—C10—H10	118.8
C4—C5—H5	119.8
C7—O1—C1—C2	−126.78 (17)	C10—N2—C7—O1	179.05 (14)
C7—O1—C1—C6	56.9 (2)	C10—N2—C7—C8	0.5 (2)
C6—C1—C2—C3	−0.5 (3)	C1—O1—C7—N2	15.5 (2)
O1—C1—C2—C3	−176.75 (15)	C1—O1—C7—C8	−165.92 (14)
C1—C2—C3—C4	−0.2 (3)	C9—N1—C8—C7	0.6 (2)
C2—C3—C4—C5	0.8 (3)	N2—C7—C8—N1	−1.1 (3)
C3—C4—C5—C6	−0.7 (3)	O1—C7—C8—N1	−179.72 (15)
C2—C1—C6—C5	0.6 (3)	C8—N1—C9—C10	0.4 (3)
O1—C1—C6—C5	176.75 (14)	C7—N2—C10—C9	0.5 (2)
C4—C5—C6—C1	0.0 (3)	N1—C9—C10—N2	−1.0 (3)