2-Phenyl-thieno[2,3-b]quinoxaline.

The title compound, C(16)H(10)N(2)S, is almost planar (r.m.s. deviation for all non-H atoms = 0.080 Å). The dihedral angle between the three fused-ring system and the phenyl ring is 9.26 (3)°. The S atom and the opposite C atom of the thio-phene ring are mutually disordered with an occupancy ratio of 0.7706 (19):0.2294 (19).

Related literature

For a related structure, see: Ramli et al. (2011 ▶). For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995 ▶). For their anti­tumour and anti­tuberculous properties, see: Abasolo et al. (1987 ▶); Rodrigo et al. (2002 ▶) and for their anti­fungal, herbicidal, anti­dyslipidemic and anti­oxidative activity, see: Jampilek et al. (2005 ▶); Sashidhara et al. (2009 ▶); Watkins et al. (2009 ▶).

Experimental

Crystal data

C16H10N2S

M = 262.32

Monoclinic,

a = 6.3875 (3) Å

b = 16.2896 (8) Å

c = 11.6054 (6) Å

β = 96.039 (3)°

V = 1200.84 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.41 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD detector diffractometer

27721 measured reflections

4821 independent reflections

4179 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.06

4821 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000098/bt5773sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000098/bt5773Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000098/bt5773Isup3.cml

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

C16H10N2S	F(000) = 544
Mr = 262.32	Dx = 1.451 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 215 reflections
a = 6.3875 (3) Å	θ = 1.8–26.7°
b = 16.2896 (8) Å	µ = 0.25 mm−1
c = 11.6054 (6) Å	T = 296 K
β = 96.039 (3)°	Prism, yellow
V = 1200.84 (10) Å3	0.41 × 0.24 × 0.21 mm
Z = 4

Bruker APEXII CCD detector diffractometer	4179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 34.0°, θmin = 2.2°
ω and φ scans	h = −10→8
27721 measured reflections	k = −25→25
4821 independent reflections	l = −15→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.5714P] where P = (Fo2 + 2Fc2)/3
4821 reflections	(Δ/σ)max = 0.004
192 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1A	0.54001 (5)	0.93619 (2)	0.62771 (5)	0.01314 (11)	0.7706 (19)
C1	0.90893 (16)	1.05183 (6)	0.61903 (9)	0.01554 (17)
H1	0.8109	1.0383	0.5569	0.019*
C6	0.87615 (15)	1.02638 (6)	0.73110 (8)	0.01308 (16)
C5	1.02452 (16)	1.04876 (6)	0.82349 (9)	0.01653 (18)
H5	1.0041	1.0331	0.8986	0.020*
C7	0.69078 (15)	0.97700 (6)	0.75084 (8)	0.01331 (17)
C4	1.20213 (17)	1.09414 (6)	0.80401 (10)	0.01888 (19)
H4	1.2993	1.1088	0.8660	0.023*
C2	1.08669 (17)	1.09714 (6)	0.59971 (10)	0.01815 (19)
H2	1.1066	1.1138	0.5250	0.022*
C3	1.23453 (17)	1.11763 (6)	0.69180 (10)	0.01883 (19)
H3	1.3547	1.1469	0.6786	0.023*
C10	0.14188 (16)	0.83199 (6)	0.87817 (8)	0.01446 (17)
C15	0.08412 (15)	0.82081 (6)	0.75707 (8)	0.01349 (16)
C9	0.42799 (16)	0.90599 (6)	0.83950 (10)	0.01732 (18)
C14	−0.10173 (16)	0.77645 (6)	0.71932 (9)	0.01765 (19)
H14	−0.1401	0.7688	0.6405	0.021*
C16	0.36948 (16)	0.89267 (6)	0.71805 (9)	0.01666 (18)
C11	0.01306 (17)	0.79725 (7)	0.95760 (9)	0.01880 (19)
H11	0.0504	0.8032	1.0368	0.023*
C12	−0.16630 (18)	0.75488 (7)	0.91879 (11)	0.0211 (2)
H12	−0.2500	0.7326	0.9718	0.025*
C13	−0.22485 (17)	0.74484 (6)	0.79834 (11)	0.0205 (2)
H13	−0.3476	0.7166	0.7728	0.025*
N2	0.20272 (14)	0.85147 (5)	0.67565 (8)	0.01643 (16)
N1	0.31701 (15)	0.87565 (6)	0.91971 (8)	0.01824 (17)
C8A	0.6155 (2)	0.95601 (9)	0.8506 (2)	0.0156 (3)	0.7706 (19)
H8A	0.6801	0.9727	0.9223	0.019*	0.7706 (19)
S1B	0.6418 (2)	0.96348 (8)	0.89788 (17)	0.0172 (4)	0.2294 (19)
C8B	0.5408 (8)	0.9415 (3)	0.6794 (7)	0.0181 (9)	0.2294 (19)
H8B	0.5454	0.9481	0.6002	0.022*	0.2294 (19)

	U11	U22	U33	U12	U13	U23
S1A	0.01306 (14)	0.01609 (14)	0.0103 (2)	−0.00218 (10)	0.00130 (12)	0.00077 (12)
C1	0.0167 (4)	0.0156 (4)	0.0146 (4)	0.0001 (3)	0.0033 (3)	−0.0008 (3)
C6	0.0123 (4)	0.0128 (3)	0.0144 (4)	0.0005 (3)	0.0020 (3)	−0.0005 (3)
C5	0.0156 (4)	0.0175 (4)	0.0162 (4)	−0.0015 (3)	0.0000 (3)	0.0002 (3)
C7	0.0127 (4)	0.0139 (3)	0.0132 (4)	0.0002 (3)	0.0005 (3)	0.0000 (3)
C4	0.0154 (4)	0.0179 (4)	0.0229 (5)	−0.0021 (3)	0.0001 (4)	−0.0012 (3)
C2	0.0199 (4)	0.0162 (4)	0.0197 (5)	−0.0003 (3)	0.0081 (4)	0.0001 (3)
C3	0.0159 (4)	0.0146 (4)	0.0268 (5)	−0.0009 (3)	0.0062 (4)	−0.0016 (3)
C10	0.0148 (4)	0.0150 (4)	0.0137 (4)	0.0015 (3)	0.0019 (3)	0.0004 (3)
C15	0.0137 (4)	0.0134 (3)	0.0134 (4)	0.0003 (3)	0.0016 (3)	0.0015 (3)
C9	0.0133 (4)	0.0158 (4)	0.0221 (5)	0.0005 (3)	−0.0012 (3)	−0.0012 (3)
C14	0.0165 (4)	0.0164 (4)	0.0193 (5)	−0.0014 (3)	−0.0018 (3)	0.0013 (3)
C16	0.0149 (4)	0.0162 (4)	0.0197 (5)	0.0023 (3)	0.0057 (3)	0.0051 (3)
C11	0.0207 (5)	0.0209 (4)	0.0157 (4)	0.0037 (4)	0.0059 (4)	0.0033 (3)
C12	0.0190 (5)	0.0192 (4)	0.0268 (5)	0.0024 (4)	0.0103 (4)	0.0071 (4)
C13	0.0151 (4)	0.0161 (4)	0.0300 (6)	−0.0019 (3)	0.0012 (4)	0.0035 (4)
N2	0.0175 (4)	0.0173 (4)	0.0149 (4)	0.0016 (3)	0.0037 (3)	0.0027 (3)
N1	0.0170 (4)	0.0197 (4)	0.0175 (4)	0.0008 (3)	−0.0009 (3)	−0.0023 (3)
C8A	0.0148 (6)	0.0193 (6)	0.0120 (7)	−0.0013 (4)	−0.0015 (5)	−0.0012 (5)
S1B	0.0150 (5)	0.0205 (5)	0.0160 (8)	−0.0038 (4)	0.0006 (5)	0.0002 (5)
C8B	0.022 (2)	0.023 (2)	0.008 (2)	0.0030 (16)	0.0028 (19)	−0.0009 (18)

S1A—C16	1.7403 (11)	C10—C15	1.4267 (14)
S1A—C7	1.7669 (10)	C15—N2	1.3663 (13)
C1—C2	1.3921 (15)	C15—C14	1.4192 (14)
C1—C6	1.4017 (14)	C9—N1	1.3236 (15)
C1—H1	0.9300	C9—C16	1.4362 (15)
C6—C5	1.4024 (14)	C9—C8A	1.4430 (19)
C6—C7	1.4692 (14)	C9—S1B	1.7338 (18)
C5—C4	1.3923 (15)	C14—C13	1.3698 (16)
C5—H5	0.9300	C14—H14	0.9300
C7—C8B	1.331 (7)	C16—N2	1.3103 (14)
C7—C8A	1.344 (2)	C16—C8B	1.460 (6)
C7—S1B	1.781 (2)	C11—C12	1.3722 (16)
C4—C3	1.3935 (16)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.4179 (17)
C2—C3	1.3903 (16)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—H3	0.9300	C8A—H8A	0.9300
C10—N1	1.3697 (13)	C8B—H8B	0.9300
C10—C11	1.4165 (14)
C16—S1A—C7	89.34 (5)	C14—C15—C10	119.36 (9)
C2—C1—C6	120.68 (9)	N1—C9—C16	122.04 (9)
C2—C1—H1	119.7	N1—C9—C8A	130.45 (13)
C6—C1—H1	119.7	C16—C9—C8A	107.50 (12)
C1—C6—C5	118.53 (9)	N1—C9—S1B	112.64 (10)
C1—C6—C7	120.54 (9)	C16—C9—S1B	125.31 (10)
C5—C6—C7	120.93 (9)	C8A—C9—S1B	17.82 (8)
C4—C5—C6	120.70 (10)	C13—C14—C15	120.34 (10)
C4—C5—H5	119.7	C13—C14—H14	119.8
C6—C5—H5	119.7	C15—C14—H14	119.8
C8B—C7—C8A	97.3 (3)	N2—C16—C9	124.28 (9)
C8B—C7—C6	132.8 (3)	N2—C16—C8B	140.3 (3)
C8A—C7—C6	129.87 (12)	C9—C16—C8B	95.3 (3)
C8B—C7—S1A	15.8 (3)	N2—C16—S1A	121.20 (8)
C8A—C7—S1A	112.77 (10)	C9—C16—S1A	114.52 (8)
C6—C7—S1A	117.35 (7)	C8B—C16—S1A	19.4 (3)
C8B—C7—S1B	110.8 (3)	C12—C11—C10	120.63 (10)
C8A—C7—S1B	13.58 (8)	C12—C11—H11	119.7
C6—C7—S1B	116.29 (8)	C10—C11—H11	119.7
S1A—C7—S1B	126.35 (7)	C11—C12—C13	120.40 (10)
C5—C4—C3	120.08 (10)	C11—C12—H12	119.8
C5—C4—H4	120.0	C13—C12—H12	119.8
C3—C4—H4	120.0	C14—C13—C12	120.42 (10)
C3—C2—C1	120.20 (10)	C14—C13—H13	119.8
C3—C2—H2	119.9	C12—C13—H13	119.8
C1—C2—H2	119.9	C16—N2—C15	114.55 (9)
C2—C3—C4	119.79 (10)	C9—N1—C10	115.11 (9)
C2—C3—H3	120.1	C7—C8A—C9	115.82 (17)
C4—C3—H3	120.1	C7—C8A—H8A	122.1
N1—C10—C11	119.16 (9)	C9—C8A—H8A	122.1
N1—C10—C15	122.00 (9)	C9—S1B—C7	84.43 (10)
C11—C10—C15	118.84 (9)	C7—C8B—C16	124.0 (6)
N2—C15—C14	118.63 (9)	C7—C8B—H8B	118.0
N2—C15—C10	122.00 (9)	C16—C8B—H8B	118.0