2,3-Bis(thio-phen-3-yl)quinoxaline.

In the title compound, C16H10N2S2, the thienyl rings are inclined to one another by 62.71 (10)°, and are inclined by 63.94 (8) and 21.35 (8)° to the quinoline mean plane [maximum deviation = 0.031 (2) Å]. In the crystal, the mol-ecules pack in a herringbone pattern, with π-π stacking inter-actions [centroid-centroid distances = 3.7381 (15) and 3.7268 (15) Å].

Related literature

For the synthesis of the title compound, and the crystal structure of the 2,3-di(thio­phen-2-yl)quinoxaline analogue, see: Crundwell et al. (2003 ▶). For the structure of a similar compound, see: Cantalupo et al. (2010 ▶).

Experimental

Crystal data

C16H10N2S2

M = 294.38

Monoclinic,

a = 15.966 (2) Å

b = 5.5741 (15) Å

c = 15.629 (4) Å

β = 98.25 (2)°

V = 1376.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.45 × 0.44 × 0.39 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.731, T max = 1.000

30279 measured reflections

4745 independent reflections

2660 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.183

S = 0.92

4745 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004248/su2562sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004248/su2562Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004248/su2562Isup3.cml

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

C16H10N2S2	F(000) = 608
Mr = 294.38	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Melting point: 406 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.966 (2) Å	Cell parameters from 3293 reflections
b = 5.5741 (15) Å	θ = 4.1–33.0°
c = 15.629 (4) Å	µ = 0.38 mm−1
β = 98.25 (2)°	T = 293 K
V = 1376.5 (6) Å3	Block, white
Z = 4	0.45 × 0.44 × 0.39 mm

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4745 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
Detector resolution: 16.1790 pixels mm-1	θmax = 32.5°, θmin = 4.2°
ω scans	h = −23→23
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→8
Tmin = 0.731, Tmax = 1.000	l = −23→23
30279 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.1124P)2] where P = (Fo2 + 2Fc2)/3
4745 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Experimental. Spectroscopic data for the title compound: 1H NMR (300 MHz, (CD3)2CO) d 8.088 (m, 1H), 7.840 (m, 1H), 7.678 (dd, 1H),7.539 (dd, 1H), 7.331 (dd, 1H); 13C NMR (300 MHz,CDCl3) d 148.81, 140.86, 140.51, 129.88, 128.90, 128.60, 127.02, 125.50.

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
N1	0.29116 (9)	0.2491 (3)	−0.02718 (9)	0.0397 (3)
C1	0.29649 (11)	0.4316 (3)	0.02698 (11)	0.0360 (4)
C2	0.22246 (11)	0.5650 (3)	0.04216 (11)	0.0373 (4)
N2	0.14724 (10)	0.5169 (3)	−0.00197 (10)	0.0423 (4)
C3	0.14154 (11)	0.3343 (4)	−0.06015 (11)	0.0406 (4)
C4	0.06234 (12)	0.2759 (4)	−0.10817 (13)	0.0531 (5)
H4	0.0146	0.3653	−0.1010	0.064*
C5	0.05559 (14)	0.0887 (4)	−0.16501 (14)	0.0586 (6)
H5	0.0034	0.0525	−0.1970	0.070*
C6	0.12757 (15)	−0.0510 (4)	−0.17559 (14)	0.0543 (5)
H6	0.1222	−0.1786	−0.2143	0.065*
C7	0.20477 (13)	0.0005 (4)	−0.12934 (13)	0.0466 (5)
H7	0.2516	−0.0929	−0.1361	0.056*
C8	0.21308 (11)	0.1952 (3)	−0.07156 (11)	0.0391 (4)
C9	0.43076 (12)	0.3380 (4)	0.12458 (12)	0.0478 (5)
H9	0.4125	0.1877	0.1400	0.057*
C10	0.38308 (11)	0.4901 (3)	0.07058 (11)	0.0367 (4)
C11	0.42746 (12)	0.7043 (4)	0.05750 (12)	0.0469 (5)
H11	0.4048	0.8291	0.0220	0.056*
C12	0.50766 (12)	0.7072 (4)	0.10303 (14)	0.0535 (5)
H12	0.5458	0.8328	0.1019	0.064*
S1	0.52814 (3)	0.45345 (12)	0.16120 (4)	0.0617 (2)
C13	0.28349 (12)	0.7946 (4)	0.17905 (12)	0.0453 (4)
H13	0.3306	0.6973	0.1940	0.054*
C14	0.22447 (11)	0.7587 (3)	0.10719 (11)	0.0387 (4)
C15	0.15839 (13)	0.9348 (4)	0.10173 (13)	0.0459 (5)
H15	0.1122	0.9381	0.0581	0.055*
C16	0.17121 (12)	1.1020 (4)	0.16974 (13)	0.0439 (4)
H16	0.1355	1.2304	0.1765	0.053*
S2	0.26067 (4)	1.03661 (12)	0.23738 (4)	0.0598 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0331 (7)	0.0495 (9)	0.0355 (7)	−0.0031 (6)	0.0019 (6)	−0.0029 (7)
C1	0.0306 (8)	0.0450 (10)	0.0321 (8)	−0.0010 (7)	0.0028 (6)	0.0029 (7)
C2	0.0324 (8)	0.0463 (11)	0.0324 (8)	−0.0016 (7)	0.0020 (6)	0.0040 (7)
N2	0.0338 (8)	0.0528 (10)	0.0387 (8)	−0.0007 (6)	0.0000 (6)	0.0033 (7)
C3	0.0352 (9)	0.0495 (11)	0.0353 (8)	−0.0035 (8)	−0.0007 (7)	0.0041 (8)
C4	0.0373 (10)	0.0663 (14)	0.0523 (11)	−0.0016 (9)	−0.0054 (8)	−0.0031 (10)
C5	0.0437 (11)	0.0759 (16)	0.0515 (12)	−0.0120 (10)	−0.0088 (9)	−0.0036 (11)
C6	0.0559 (12)	0.0628 (14)	0.0414 (10)	−0.0125 (10)	−0.0028 (9)	−0.0093 (10)
C7	0.0445 (10)	0.0530 (12)	0.0418 (10)	−0.0057 (8)	0.0043 (8)	−0.0053 (8)
C8	0.0346 (8)	0.0497 (11)	0.0322 (8)	−0.0066 (7)	0.0019 (6)	0.0027 (8)
C9	0.0388 (10)	0.0525 (12)	0.0490 (11)	−0.0023 (8)	−0.0045 (8)	0.0020 (9)
C10	0.0306 (8)	0.0470 (10)	0.0322 (8)	−0.0010 (7)	0.0030 (6)	−0.0044 (7)
C11	0.0424 (10)	0.0518 (12)	0.0461 (10)	−0.0055 (8)	0.0049 (8)	0.0037 (9)
C12	0.0373 (10)	0.0597 (13)	0.0635 (13)	−0.0132 (9)	0.0076 (9)	−0.0124 (11)
S1	0.0398 (3)	0.0779 (5)	0.0612 (4)	0.0005 (2)	−0.0134 (2)	−0.0057 (3)
C13	0.0437 (10)	0.0523 (11)	0.0398 (9)	0.0014 (9)	0.0052 (7)	−0.0036 (9)
C14	0.0358 (8)	0.0446 (10)	0.0368 (8)	−0.0011 (7)	0.0092 (7)	0.0008 (7)
C15	0.0408 (10)	0.0519 (12)	0.0462 (10)	0.0024 (8)	0.0104 (8)	0.0049 (9)
C16	0.0397 (9)	0.0428 (10)	0.0518 (11)	0.0044 (8)	0.0154 (8)	0.0022 (8)
S2	0.0572 (4)	0.0705 (4)	0.0532 (3)	−0.0039 (3)	0.0130 (3)	−0.0152 (3)

N1—C1	1.318 (2)	C9—C10	1.351 (3)
N1—C8	1.370 (2)	C9—S1	1.7040 (19)
C1—C2	1.445 (2)	C9—H9	0.9300
C1—C10	1.487 (2)	C10—C11	1.418 (3)
C2—N2	1.324 (2)	C11—C12	1.373 (3)
C2—C14	1.480 (2)	C11—H11	0.9300
N2—C3	1.359 (2)	C12—S1	1.688 (2)
C3—C8	1.413 (3)	C12—H12	0.9300
C3—C4	1.413 (2)	C13—C14	1.373 (2)
C4—C5	1.365 (3)	C13—S2	1.697 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.417 (3)	C14—C15	1.435 (3)
C5—H5	0.9300	C15—C16	1.406 (3)
C6—C7	1.367 (3)	C15—H15	0.9300
C6—H6	0.9300	C16—S2	1.690 (2)
C7—C8	1.406 (3)	C16—H16	0.9300
C7—H7	0.9300
C1—N1—C8	117.70 (15)	C10—C9—S1	112.20 (16)
N1—C1—C2	121.58 (16)	C10—C9—H9	123.9
N1—C1—C10	115.70 (15)	S1—C9—H9	123.9
C2—C1—C10	122.72 (16)	C9—C10—C11	111.71 (17)
N2—C2—C1	120.83 (17)	C9—C10—C1	123.50 (17)
N2—C2—C14	115.76 (16)	C11—C10—C1	124.71 (16)
C1—C2—C14	123.41 (15)	C12—C11—C10	112.53 (18)
C2—N2—C3	117.98 (16)	C12—C11—H11	123.7
N2—C3—C8	121.18 (16)	C10—C11—H11	123.7
N2—C3—C4	119.79 (17)	C11—C12—S1	111.33 (16)
C8—C3—C4	118.99 (18)	C11—C12—H12	124.3
C5—C4—C3	120.2 (2)	S1—C12—H12	124.3
C5—C4—H4	119.9	C12—S1—C9	92.21 (10)
C3—C4—H4	119.9	C14—C13—S2	112.35 (15)
C4—C5—C6	120.42 (19)	C14—C13—H13	123.8
C4—C5—H5	119.8	S2—C13—H13	123.8
C6—C5—H5	119.8	C13—C14—C15	111.18 (18)
C7—C6—C5	120.5 (2)	C13—C14—C2	127.79 (17)
C7—C6—H6	119.7	C15—C14—C2	121.00 (17)
C5—C6—H6	119.7	C16—C15—C14	112.50 (18)
C6—C7—C8	119.8 (2)	C16—C15—H15	123.8
C6—C7—H7	120.1	C14—C15—H15	123.8
C8—C7—H7	120.1	C15—C16—S2	110.37 (15)
N1—C8—C7	119.34 (17)	C15—C16—H16	124.8
N1—C8—C3	120.58 (17)	S2—C16—H16	124.8
C7—C8—C3	120.08 (16)	C16—S2—C13	93.60 (10)