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

The two aromatic systems in the title compound, C(14)H(10)N(2)O, 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 = 222.24

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.114

S = 1.03

2398 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031243/im2084sup1.cif

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

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

C14H10N2O	F(000) = 464
Mr = 222.24	Dx = 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

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

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(Fo2) + (0.0648P)2 + 0.2602P] where P = (Fo2 + 2Fc2)/3
2398 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)