Phenyl pyrazin-2-yl ether

Idris, A.; Afiffin, A.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536808040099

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o7

doi:10.1107/S1600536808040099

Open

access

Phenyl pyrazin-2-yl ether

Azila Idris,^a Azhar Afiffin,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 November 2008; accepted 28 November 2008; online 3 December 2008)

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, P 2₁ /c
a = 5.704 (1) Å
b = 8.557 (2) Å
c = 17.595 (4) Å
β = 94.382 (3)°
V = 856.4 (3) Å³
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[F² > 2σ(F²)] = 0.046
wR(F²) = 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040099/hb2867sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040099/hb2867Isup2.hkl

checkCIF report

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Phenyl pyrazin-2-yl ether top

Crystal data top

C₁₀H₈N₂O	F(000) = 360
M_r = 172.18	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0572P)²] where P = (F_o² + 2F_c²)/3
1950 reflections	(Δ/σ)_max = 0.001
118 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₀H₈N₂O	V = 856.4 (3) Å³
M_r = 172.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.704 (1) Å	µ = 0.09 mm⁻¹
b = 8.557 (2) Å	T = 100 K
c = 17.595 (4) Å	0.20 × 0.15 × 0.10 mm
β = 94.382 (3)°

Data collection top

Bruker SMART APEX diffractometer	1207 reflections with I > 2σ(I)
4641 measured reflections	R_int = 0.042
1950 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 0.97	Δρ_max = 0.20 e Å⁻³
1950 reflections	Δρ_min = −0.27 e Å⁻³
118 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂O
M_r	172.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.704 (1), 8.557 (2), 17.595 (4)
β (°)	94.382 (3)
V (Å³)	856.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4641, 1950, 1207
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 0.97
No. of reflections	1950
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

We thank the University of Malaya for supporting this study (grant No. FS358/2008 A).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2105. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar