A second monoclinic modification of phenyl quinoxalin-2-yl ether

Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536808031243

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2165

doi:10.1107/S1600536808031243

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A second monoclinic modification of phenyl quinoxalin-2-yl ether

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 10 September 2008; accepted 26 September 2008; online 22 October 2008)

The two aromatic systems in the title compound, C₁₄H₁₀N₂O, enclose a dihedral angle of 77.9 (1)°, and the C—O—C inter-ring bond angle is 117.6 (1)°.

Related literature

Another polymorph of this compound has recently been described in the C2/c space group; see Hassan et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Monoclinic, P 2₁ /n
a = 7.9447 (2) Å
b = 6.5169 (1) Å
c = 20.2992 (5) Å
β = 91.983 (1)°
V = 1050.36 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
7016 measured reflections
2398 independent reflections
1960 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.114
S = 1.03
2398 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.23 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/S1600536808031243/im2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031243/im2084Isup2.hkl

checkCIF report

Comment top

The compound was recently described in the C2/c space group with the two aromatic substituents in C₁₄H₁₀N₂O enclosing a dihedral angle of 63.8 (1)°. The bond angle at oxygen measures to 118.2 (1)° (Hassan et al., 2008). In the P2₁/n modification described herein (Scheme I, Fig. 1), the two aromatic systems show a dihedral angle of 77.9 (1)° and they subtend an angle of 117.6 (1)° at oxygen.

Related literature top

The compound has been recently described in the C2/c space group; see Hassan et al. (2008).

Experimental top

The monoclinic modification was obtained when the C2/c modification of quinoxalinyl phenyl ether was recrystallized from ethanol in the presence of a small quantity of manganese acetate. Slow evaporation of the solvent gave colorless crystals mixed with unchanged manganese acetate.

Computing details top

Data collection: APEX2 or SMART? (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. Thermal ellipsoid plot (Barbour, 2001) of C₁₄H₁₀N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

phenyl quinoxalin-2-yl ether top

Crystal data top

C₁₄H₁₀N₂O	F(000) = 464
M_r = 222.24	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2712 reflections
a = 7.9447 (2) Å	θ = 2.7–28.4°
b = 6.5169 (1) Å	µ = 0.09 mm⁻¹
c = 20.2992 (5) Å	T = 100 K
β = 91.983 (1)°	Block, colorless
V = 1050.36 (4) Å³	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1960 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −10→9
7016 measured reflections	k = −8→8
2398 independent reflections	l = −26→26

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0648P)² + 0.2602P] where P = (F_o² + 2F_c²)/3
2398 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₁₀N₂O	V = 1050.36 (4) Å³
M_r = 222.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9447 (2) Å	µ = 0.09 mm⁻¹
b = 6.5169 (1) Å	T = 100 K
c = 20.2992 (5) Å	0.40 × 0.20 × 0.10 mm
β = 91.983 (1)°

Data collection top

Bruker SMART APEX diffractometer	1960 reflections with I > 2σ(I)
7016 measured reflections	R_int = 0.021
2398 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
2398 reflections	Δρ_min = −0.23 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.34884 (10)	0.24973 (13)	0.66577 (4)	0.0189 (2)
N1	0.58503 (12)	0.26591 (14)	0.60174 (5)	0.0150 (2)
N2	0.35723 (12)	0.23610 (14)	0.49088 (5)	0.0153 (2)
C1	0.45193 (13)	0.28653 (19)	0.72247 (5)	0.0170 (3)
C2	0.44960 (15)	0.48057 (19)	0.74939 (6)	0.0199 (3)
H2	0.3836	0.5863	0.7292	0.024*
C3	0.54551 (15)	0.5187 (2)	0.80653 (6)	0.0233 (3)
H3	0.5461	0.6519	0.8255	0.028*
C4	0.64037 (15)	0.3635 (2)	0.83596 (6)	0.0232 (3)
H4	0.7066	0.3906	0.8749	0.028*
C5	0.63876 (15)	0.1689 (2)	0.80870 (6)	0.0242 (3)
H5	0.7029	0.0622	0.8293	0.029*
C6	0.54360 (15)	0.1286 (2)	0.75122 (6)	0.0219 (3)
H6	0.5419	−0.0047	0.7323	0.026*
C7	0.42352 (15)	0.25028 (16)	0.60650 (5)	0.0148 (2)
C8	0.30741 (14)	0.23391 (17)	0.55103 (6)	0.0158 (3)
H8	0.1905	0.2211	0.5586	0.019*
C9	0.52855 (14)	0.25143 (16)	0.48299 (5)	0.0139 (2)
C10	0.59172 (15)	0.25296 (17)	0.41912 (5)	0.0160 (3)
H10	0.5161	0.2467	0.3819	0.019*
C11	0.76232 (15)	0.26345 (17)	0.41025 (6)	0.0174 (3)
H11	0.8043	0.2630	0.3670	0.021*
C12	0.87492 (15)	0.27483 (18)	0.46528 (6)	0.0179 (3)
H12	0.9927	0.2808	0.4589	0.021*
C13	0.81557 (14)	0.27741 (18)	0.52800 (6)	0.0167 (3)
H13	0.8925	0.2878	0.5647	0.020*
C14	0.64163 (14)	0.26477 (16)	0.53833 (5)	0.0141 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0148 (4)	0.0292 (5)	0.0127 (4)	−0.0019 (3)	0.0008 (3)	−0.0024 (3)
N1	0.0146 (5)	0.0160 (5)	0.0144 (5)	0.0003 (3)	−0.0008 (4)	−0.0002 (3)
N2	0.0155 (5)	0.0137 (5)	0.0166 (5)	0.0004 (3)	−0.0011 (4)	−0.0005 (4)
C1	0.0119 (5)	0.0277 (6)	0.0116 (5)	−0.0025 (4)	0.0025 (4)	0.0000 (4)
C2	0.0208 (6)	0.0237 (6)	0.0153 (5)	−0.0008 (5)	0.0014 (4)	0.0026 (4)
C3	0.0253 (6)	0.0276 (7)	0.0170 (6)	−0.0061 (5)	0.0017 (5)	−0.0019 (5)
C4	0.0160 (6)	0.0396 (8)	0.0140 (5)	−0.0056 (5)	0.0002 (4)	0.0014 (5)
C5	0.0164 (6)	0.0368 (7)	0.0195 (6)	0.0047 (5)	0.0025 (4)	0.0076 (5)
C6	0.0199 (6)	0.0262 (7)	0.0199 (6)	0.0018 (5)	0.0042 (4)	−0.0001 (5)
C7	0.0168 (5)	0.0137 (5)	0.0139 (5)	0.0000 (4)	0.0014 (4)	−0.0007 (4)
C8	0.0134 (5)	0.0162 (6)	0.0177 (6)	0.0003 (4)	−0.0005 (4)	−0.0009 (4)
C9	0.0146 (5)	0.0113 (5)	0.0158 (6)	0.0011 (4)	−0.0008 (4)	0.0001 (4)
C10	0.0188 (6)	0.0148 (6)	0.0142 (5)	0.0015 (4)	−0.0024 (4)	0.0002 (4)
C11	0.0200 (6)	0.0186 (6)	0.0138 (5)	0.0017 (4)	0.0030 (4)	0.0013 (4)
C12	0.0147 (5)	0.0195 (6)	0.0196 (6)	0.0009 (4)	0.0023 (4)	0.0011 (4)
C13	0.0145 (5)	0.0192 (6)	0.0161 (6)	0.0009 (4)	−0.0020 (4)	0.0007 (4)
C14	0.0158 (6)	0.0121 (5)	0.0142 (5)	0.0007 (4)	−0.0002 (4)	0.0005 (4)

Geometric parameters (Å, º) top

O1—C7	1.3598 (14)	C5—H5	0.9500
O1—C1	1.4099 (13)	C6—H6	0.9500
N1—C7	1.2941 (15)	C7—C8	1.4346 (15)
N1—C14	1.3781 (14)	C8—H8	0.9500
N2—C8	1.2966 (15)	C9—C10	1.4066 (15)
N2—C9	1.3796 (15)	C9—C14	1.4165 (16)
C1—C2	1.3780 (17)	C10—C11	1.3751 (16)
C1—C6	1.3786 (17)	C10—H10	0.9500
C2—C3	1.3880 (16)	C11—C12	1.4086 (16)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.3847 (18)	C12—C13	1.3730 (15)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.383 (2)	C13—C14	1.4073 (16)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3931 (17)

C7—O1—C1	117.58 (9)	O1—C7—C8	113.94 (10)
C7—N1—C14	115.20 (10)	N2—C8—C7	121.96 (11)
C8—N2—C9	116.40 (10)	N2—C8—H8	119.0
C2—C1—C6	122.08 (11)	C7—C8—H8	119.0
C2—C1—O1	117.68 (10)	N2—C9—C10	119.51 (10)
C6—C1—O1	120.14 (11)	N2—C9—C14	120.90 (10)
C1—C2—C3	118.77 (11)	C10—C9—C14	119.59 (10)
C1—C2—H2	120.6	C11—C10—C9	120.38 (10)
C3—C2—H2	120.6	C11—C10—H10	119.8
C4—C3—C2	120.30 (12)	C9—C10—H10	119.8
C4—C3—H3	119.8	C10—C11—C12	120.04 (11)
C2—C3—H3	119.8	C10—C11—H11	120.0
C5—C4—C3	119.98 (11)	C12—C11—H11	120.0
C5—C4—H4	120.0	C13—C12—C11	120.46 (11)
C3—C4—H4	120.0	C13—C12—H12	119.8
C4—C5—C6	120.32 (12)	C11—C12—H12	119.8
C4—C5—H5	119.8	C12—C13—C14	120.53 (10)
C6—C5—H5	119.8	C12—C13—H13	119.7
C1—C6—C5	118.53 (12)	C14—C13—H13	119.7
C1—C6—H6	120.7	N1—C14—C13	119.52 (10)
C5—C6—H6	120.7	N1—C14—C9	121.50 (10)
N1—C7—O1	122.03 (10)	C13—C14—C9	118.98 (11)
N1—C7—C8	124.02 (11)

C7—O1—C1—C2	100.70 (12)	O1—C7—C8—N2	178.65 (10)
C7—O1—C1—C6	−82.79 (13)	C8—N2—C9—C10	179.47 (10)
C6—C1—C2—C3	1.36 (17)	C8—N2—C9—C14	−0.26 (15)
O1—C1—C2—C3	177.79 (10)	N2—C9—C10—C11	−178.53 (10)
C1—C2—C3—C4	−0.52 (17)	C14—C9—C10—C11	1.21 (16)
C2—C3—C4—C5	−0.52 (18)	C9—C10—C11—C12	−0.64 (16)
C3—C4—C5—C6	0.77 (18)	C10—C11—C12—C13	−0.59 (17)
C2—C1—C6—C5	−1.11 (17)	C11—C12—C13—C14	1.22 (17)
O1—C1—C6—C5	−177.45 (10)	C7—N1—C14—C13	−178.90 (10)
C4—C5—C6—C1	0.02 (17)	C7—N1—C14—C9	1.19 (15)
C14—N1—C7—O1	−179.82 (10)	C12—C13—C14—N1	179.46 (10)
C14—N1—C7—C8	−0.37 (15)	C12—C13—C14—C9	−0.63 (16)
C1—O1—C7—N1	5.91 (15)	N2—C9—C14—N1	−0.94 (16)
C1—O1—C7—C8	−173.59 (10)	C10—C9—C14—N1	179.33 (10)
C9—N2—C8—C7	1.10 (15)	N2—C9—C14—C13	179.15 (10)
N1—C7—C8—N2	−0.84 (17)	C10—C9—C14—C13	−0.58 (15)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.9447 (2), 6.5169 (1), 20.2992 (5)
β (°)	91.983 (1)
V (Å³)	1050.36 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7016, 2398, 1960
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.114, 1.03
No. of reflections	2398
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

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

Acknowledgements

The authors thank the University of Malaya for supporting this study (grant No. F2358/2008A).

References

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Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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