1-Naphthyl quinoxalin-2-yl ether

Hassan, N.D.; Tajuddin, H.A.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809007867

organic compounds

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Volume 65| Part 4| April 2009| Page o731

doi:10.1107/S1600536809007867

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1-Naphthyl quinoxalin-2-yl ether

Noor Doha Hassan,^a Hairul Anuar Tajuddin,^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 2 March 2009; accepted 4 March 2009; online 11 March 2009)

In the crystal structure of the title compound, C₁₈H₁₂N₂O, the dihedral angle between the two fused-ring systems is 84.3 (1) °; the C—O—C angle at the ether O atom is 117.31 (18)°.

Related literature

For the crystal structure of the two forms of quinoxalinyl 2-phenyl ether, see: Abdullah & Ng (2008 ); Hassan et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₂N₂O
M_r = 272.30
Orthorhombic, A b a 2
a = 18.2758 (6) Å
b = 18.5123 (6) Å
c = 7.7947 (3) Å
V = 2637.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 118 K
0.12 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
12370 measured reflections
1626 independent reflections
1316 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.02
1626 reflections
190 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007867/tk2386sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007867/tk2386Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of the two forms of quinoxalinyl 2-phenyl ether, see: Abdullah & Ng (2008); Hassan et al. (2008).

Experimental top

1-Naphthol (2.88 g, 20 mmol) was mixed with sodium hydroxide (0.08 g, 20 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-chloroquinoxaline (3.29 g, 20 mmol) at 423–433 K for 6 h. The product was dissolved in water and the solution extracted with chloroform. The chloroform phase was dried over sodium sulfate; the evaporation of the solvent gave a product that was recrystallized from a chloroform/ether mixture.

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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the molecule of C₁₈H₁₂N₂O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

1-Naphthyl quinoxalin-2-yl ether top

Crystal data top

C₁₈H₁₂N₂O	F(000) = 1136
M_r = 272.30	D_x = 1.372 Mg m⁻³
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 1495 reflections
a = 18.2758 (6) Å	θ = 2.2–21.2°
b = 18.5123 (6) Å	µ = 0.09 mm⁻¹
c = 7.7947 (3) Å	T = 118 K
V = 2637.2 (2) Å³	Prism, colorless
Z = 8	0.12 × 0.04 × 0.02 mm

Data collection top

Bruker SMART APEX diffractometer	1316 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.071
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −22→23
12370 measured reflections	k = −24→23
1626 independent reflections	l = −10→10

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.046P)² + 0.5804P] where P = (F_o² + 2F_c²)/3
1626 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₂N₂O	V = 2637.2 (2) Å³
M_r = 272.30	Z = 8
Orthorhombic, Aba2	Mo Kα radiation
a = 18.2758 (6) Å	µ = 0.09 mm⁻¹
b = 18.5123 (6) Å	T = 118 K
c = 7.7947 (3) Å	0.12 × 0.04 × 0.02 mm

Data collection top

Bruker SMART APEX diffractometer	1316 reflections with I > 2σ(I)
12370 measured reflections	R_int = 0.071
1626 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
1626 reflections	Δρ_min = −0.24 e Å⁻³
190 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.19391 (9)	0.24366 (9)	0.5000 (2)	0.0217 (4)
N1	0.15328 (11)	0.34927 (11)	0.3713 (3)	0.0192 (5)
N2	0.30285 (11)	0.38838 (11)	0.3387 (3)	0.0218 (5)
C1	0.12235 (13)	0.21546 (12)	0.4887 (4)	0.0192 (5)
C2	0.07744 (14)	0.22066 (13)	0.6269 (4)	0.0222 (6)
H2	0.0930	0.2454	0.7273	0.027*
C3	0.00734 (14)	0.18873 (13)	0.6196 (3)	0.0234 (6)
H3	−0.0246	0.1922	0.7155	0.028*
C4	−0.01480 (14)	0.15306 (13)	0.4762 (3)	0.0231 (6)
H4	−0.0619	0.1314	0.4737	0.028*
C5	0.03121 (13)	0.14761 (12)	0.3301 (3)	0.0198 (5)
C6	0.00887 (15)	0.11230 (14)	0.1784 (4)	0.0269 (6)
H6	−0.0381	0.0903	0.1737	0.032*
C7	0.05358 (16)	0.10925 (15)	0.0388 (4)	0.0301 (7)
H7	0.0375	0.0857	−0.0627	0.036*
C8	0.12373 (16)	0.14110 (15)	0.0448 (4)	0.0278 (6)
H8	0.1546	0.1388	−0.0531	0.033*
C9	0.14764 (14)	0.17502 (13)	0.1890 (4)	0.0219 (6)
H9	0.1952	0.1957	0.1917	0.026*
C10	0.10190 (13)	0.17973 (13)	0.3355 (3)	0.0180 (5)
C11	0.20655 (14)	0.30943 (13)	0.4253 (3)	0.0189 (5)
C12	0.28187 (14)	0.32836 (13)	0.4113 (3)	0.0213 (6)
H12	0.3178	0.2964	0.4560	0.026*
C13	0.24804 (15)	0.43279 (12)	0.2773 (3)	0.0190 (5)
C14	0.26686 (14)	0.49812 (13)	0.1965 (4)	0.0232 (6)
H14	0.3168	0.5114	0.1841	0.028*
C15	0.21262 (15)	0.54275 (14)	0.1356 (4)	0.0247 (6)
H15	0.2253	0.5866	0.0798	0.030*
C16	0.13869 (15)	0.52397 (13)	0.1552 (4)	0.0231 (6)
H16	0.1017	0.5552	0.1123	0.028*
C17	0.11934 (14)	0.46108 (13)	0.2357 (3)	0.0212 (6)
H17	0.0691	0.4494	0.2501	0.025*
C18	0.17350 (13)	0.41378 (13)	0.2971 (3)	0.0190 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0185 (9)	0.0192 (9)	0.0275 (10)	−0.0015 (7)	−0.0032 (8)	0.0043 (8)
N1	0.0177 (11)	0.0189 (10)	0.0211 (12)	−0.0005 (8)	−0.0005 (8)	0.0002 (9)
N2	0.0202 (11)	0.0228 (11)	0.0223 (11)	−0.0011 (8)	−0.0006 (10)	−0.0001 (10)
C1	0.0154 (13)	0.0156 (11)	0.0266 (14)	0.0005 (9)	−0.0035 (12)	0.0063 (11)
C2	0.0246 (14)	0.0183 (12)	0.0237 (14)	0.0038 (10)	−0.0013 (12)	0.0002 (11)
C3	0.0228 (14)	0.0215 (13)	0.0259 (15)	0.0046 (10)	0.0077 (12)	0.0030 (12)
C4	0.0164 (13)	0.0212 (12)	0.0316 (16)	0.0026 (9)	0.0011 (12)	0.0054 (12)
C5	0.0179 (13)	0.0159 (12)	0.0255 (14)	0.0015 (10)	−0.0038 (11)	0.0057 (11)
C6	0.0244 (14)	0.0236 (13)	0.0326 (16)	−0.0003 (11)	−0.0065 (13)	−0.0009 (13)
C7	0.0321 (16)	0.0316 (15)	0.0266 (16)	0.0045 (12)	−0.0094 (13)	−0.0040 (13)
C8	0.0325 (15)	0.0312 (15)	0.0198 (14)	0.0087 (12)	0.0021 (12)	0.0017 (12)
C9	0.0206 (13)	0.0194 (12)	0.0257 (14)	0.0031 (10)	0.0009 (11)	0.0065 (12)
C10	0.0184 (12)	0.0152 (11)	0.0205 (13)	0.0019 (9)	−0.0007 (11)	0.0045 (10)
C11	0.0225 (14)	0.0169 (12)	0.0172 (12)	−0.0021 (10)	−0.0020 (11)	−0.0011 (10)
C12	0.0193 (14)	0.0229 (13)	0.0217 (13)	0.0016 (10)	−0.0012 (11)	−0.0018 (11)
C13	0.0191 (12)	0.0193 (11)	0.0184 (13)	0.0000 (10)	−0.0003 (10)	−0.0023 (10)
C14	0.0226 (14)	0.0226 (12)	0.0243 (14)	−0.0037 (10)	0.0031 (12)	−0.0002 (12)
C15	0.0312 (15)	0.0203 (12)	0.0225 (14)	−0.0016 (11)	0.0019 (12)	0.0017 (11)
C16	0.0243 (14)	0.0199 (12)	0.0252 (14)	0.0032 (10)	−0.0034 (12)	−0.0006 (11)
C17	0.0192 (13)	0.0199 (12)	0.0245 (14)	−0.0004 (10)	−0.0005 (11)	−0.0023 (11)
C18	0.0205 (13)	0.0160 (11)	0.0204 (13)	−0.0010 (10)	0.0000 (11)	−0.0043 (11)

Geometric parameters (Å, º) top

O1—C11	1.369 (3)	C7—C8	1.412 (4)
O1—C1	1.411 (3)	C7—H7	0.9500
N1—C11	1.292 (3)	C8—C9	1.360 (4)
N1—C18	1.378 (3)	C8—H8	0.9500
N2—C12	1.304 (3)	C9—C10	1.418 (3)
N2—C13	1.382 (3)	C9—H9	0.9500
C1—C2	1.358 (4)	C11—C12	1.425 (3)
C1—C10	1.415 (3)	C12—H12	0.9500
C2—C3	1.412 (4)	C13—C14	1.406 (3)
C2—H2	0.9500	C13—C18	1.415 (4)
C3—C4	1.360 (4)	C14—C15	1.375 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.419 (4)	C15—C16	1.404 (4)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.411 (4)	C16—C17	1.369 (4)
C5—C10	1.423 (3)	C16—H16	0.9500
C6—C7	1.362 (4)	C17—C18	1.405 (3)
C6—H6	0.9500	C17—H17	0.9500

C11—O1—C1	117.31 (18)	C10—C9—H9	119.8
C11—N1—C18	115.4 (2)	C1—C10—C9	123.5 (2)
C12—N2—C13	116.4 (2)	C1—C10—C5	117.4 (2)
C2—C1—O1	119.0 (2)	C9—C10—C5	119.1 (2)
C2—C1—C10	122.9 (2)	N1—C11—O1	121.3 (2)
O1—C1—C10	118.1 (2)	N1—C11—C12	124.2 (2)
C1—C2—C3	119.1 (2)	O1—C11—C12	114.5 (2)
C1—C2—H2	120.5	N2—C12—C11	121.8 (2)
C3—C2—H2	120.5	N2—C12—H12	119.1
C4—C3—C2	120.4 (2)	C11—C12—H12	119.1
C4—C3—H3	119.8	N2—C13—C14	119.3 (2)
C2—C3—H3	119.8	N2—C13—C18	120.8 (2)
C3—C4—C5	121.2 (2)	C14—C13—C18	119.9 (2)
C3—C4—H4	119.4	C15—C14—C13	119.7 (2)
C5—C4—H4	119.4	C15—C14—H14	120.2
C6—C5—C4	122.3 (2)	C13—C14—H14	120.2
C6—C5—C10	118.8 (2)	C14—C15—C16	120.5 (2)
C4—C5—C10	119.0 (2)	C14—C15—H15	119.7
C7—C6—C5	121.0 (2)	C16—C15—H15	119.7
C7—C6—H6	119.5	C17—C16—C15	120.6 (2)
C5—C6—H6	119.5	C17—C16—H16	119.7
C6—C7—C8	120.0 (3)	C15—C16—H16	119.7
C6—C7—H7	120.0	C16—C17—C18	120.3 (2)
C8—C7—H7	120.0	C16—C17—H17	119.9
C9—C8—C7	120.8 (3)	C18—C17—H17	119.9
C9—C8—H8	119.6	N1—C18—C17	119.6 (2)
C7—C8—H8	119.6	N1—C18—C13	121.3 (2)
C8—C9—C10	120.3 (2)	C17—C18—C13	119.1 (2)
C8—C9—H9	119.8

C11—O1—C1—C2	−101.4 (3)	C18—N1—C11—O1	−179.3 (2)
C11—O1—C1—C10	81.6 (3)	C18—N1—C11—C12	−0.3 (4)
O1—C1—C2—C3	−176.3 (2)	C1—O1—C11—N1	10.9 (3)
C10—C1—C2—C3	0.5 (3)	C1—O1—C11—C12	−168.2 (2)
C1—C2—C3—C4	0.2 (3)	C13—N2—C12—C11	0.4 (4)
C2—C3—C4—C5	−0.7 (4)	N1—C11—C12—N2	−1.0 (4)
C3—C4—C5—C6	−178.6 (2)	O1—C11—C12—N2	178.1 (2)
C3—C4—C5—C10	0.5 (3)	C12—N2—C13—C14	−179.6 (2)
C4—C5—C6—C7	178.6 (2)	C12—N2—C13—C18	1.4 (4)
C10—C5—C6—C7	−0.5 (4)	N2—C13—C14—C15	−179.7 (2)
C5—C6—C7—C8	0.6 (4)	C18—C13—C14—C15	−0.7 (4)
C6—C7—C8—C9	0.1 (4)	C13—C14—C15—C16	0.7 (4)
C7—C8—C9—C10	−0.8 (4)	C14—C15—C16—C17	0.2 (4)
C2—C1—C10—C9	178.8 (2)	C15—C16—C17—C18	−1.2 (4)
O1—C1—C10—C9	−4.4 (3)	C11—N1—C18—C17	−179.5 (2)
C2—C1—C10—C5	−0.7 (3)	C11—N1—C18—C13	2.1 (3)
O1—C1—C10—C5	176.1 (2)	C16—C17—C18—N1	−177.3 (2)
C8—C9—C10—C1	−178.6 (2)	C16—C17—C18—C13	1.2 (4)
C8—C9—C10—C5	0.9 (4)	N2—C13—C18—N1	−2.8 (4)
C6—C5—C10—C1	179.3 (2)	C14—C13—C18—N1	178.2 (2)
C4—C5—C10—C1	0.2 (3)	N2—C13—C18—C17	178.8 (2)
C6—C5—C10—C9	−0.2 (3)	C14—C13—C18—C17	−0.3 (4)
C4—C5—C10—C9	−179.3 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂N₂O
M_r	272.30
Crystal system, space group	Orthorhombic, Aba2
Temperature (K)	118
a, b, c (Å)	18.2758 (6), 18.5123 (6), 7.7947 (3)
V (Å³)	2637.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.04 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12370, 1626, 1316
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.087, 1.02
No. of reflections	1626
No. of parameters	190
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for supporting this study (FS358/2008 A).

References

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