2,3-Dithien-2-yl­quinoxaline

In the title compound, C₁₆H₁₀N₂S₂, (I), which was synthesized via the reaction of 2,2'-thenil and 1,2-phenyl­enedi­amine, the thienyl rings display ideal geometries, with no evidence of ring-flip disorders often found with unsubstituted terminal 2-thienyl rings [Zheng, Wang, Liu, Carducci, Peyghambarian & Jabbourb (2002). Acta Cryst. C58, m50-m52].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.061
• wR factor = 0.122
• Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
          Tmin and Tmax reported:      0.753     1.000
          Tmin' and Tmax expected:      0.867     0.954
          RR' =      0.829
          Please check that your absorption correction is appropriate.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

2,3-Dithien-2-ylquinoxaline

Crystal data

C16H10N2S2	F(000) = 608
Mr = 294.38	Dx = 1.475 Mg m^−3
Monoclinic, P21/c	Melting point: 145 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.521 (3) Å	Cell parameters from 11758 reflections
b = 5.2071 (14) Å	θ = 2.1–28.3°
c = 22.745 (7) Å	µ = 0.39 mm^−1
β = 103.681 (4)°	T = 293 K
V = 1325.8 (6) Å^3	Needle, yellow
Z = 4	0.36 × 0.23 × 0.12 mm

Data collection

Bruker SMART P3/512CCD diffractometer	2617 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.753, Tmax = 1.000	k = −6→6
10027 measured reflections	l = −27→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 1.0471P] where P = (Fo^2 + 2Fc^2)/3
2617 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.3645 (2)	0.3248 (5)	−0.06163 (11)	0.0342 (6)
C1	0.2844 (2)	0.1437 (6)	−0.06298 (12)	0.0298 (6)
N2	0.2168 (2)	0.1568 (5)	−0.17120 (10)	0.0339 (6)
C2	0.2089 (2)	0.0560 (6)	−0.11919 (12)	0.0295 (6)
C3	0.2986 (3)	0.3467 (6)	−0.16997 (13)	0.0346 (7)
C4	0.3094 (3)	0.4609 (7)	−0.22448 (15)	0.0476 (9)
H4A	0.2614	0.4051	−0.2610	0.057*
C5	0.3896 (3)	0.6520 (7)	−0.22394 (16)	0.0512 (9)
H5A	0.3955	0.7282	−0.2601	0.061*
C6	0.4640 (3)	0.7355 (7)	−0.16904 (16)	0.0481 (9)
H6A	0.5191	0.8660	−0.1692	0.058*
C7	0.4562 (3)	0.6274 (6)	−0.11584 (15)	0.0422 (8)
H7A	0.5056	0.6839	−0.0797	0.051*
C8	0.3733 (2)	0.4296 (6)	−0.11548 (13)	0.0330 (7)
C9	0.2743 (2)	0.0475 (6)	−0.00336 (13)	0.0323 (7)
C10	0.3374 (3)	−0.1392 (6)	0.03159 (13)	0.0391 (8)
H10A	0.3982	−0.2326	0.0210	0.047*
C11	0.3004 (3)	−0.1768 (7)	0.08615 (14)	0.0446 (8)
H11A	0.3340	−0.2986	0.1151	0.053*
C12	0.2121 (3)	−0.0183 (6)	0.09152 (14)	0.0424 (8)
H12A	0.1773	−0.0171	0.1245	0.051*
S1	0.17130 (8)	0.18052 (17)	0.03086 (4)	0.0460 (3)
C13	0.1193 (2)	−0.1475 (5)	−0.12294 (12)	0.0294 (6)
C14	0.0945 (3)	−0.3165 (6)	−0.08138 (13)	0.0345 (7)
H14A	0.1354	−0.3183	−0.0409	0.041*
C15	0.0012 (3)	−0.4866 (6)	−0.10608 (14)	0.0357 (7)
H15A	−0.0257	−0.6135	−0.0837	0.043*
C16	−0.0453 (3)	−0.4470 (6)	−0.16547 (14)	0.0395 (7)
H16A	−0.1079	−0.5420	−0.1887	0.047*
S2	0.02454 (7)	−0.20146 (17)	−0.19284 (3)	0.0425 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0300 (13)	0.0354 (15)	0.0362 (14)	0.0013 (11)	0.0057 (11)	−0.0025 (12)
C1	0.0264 (14)	0.0308 (16)	0.0320 (15)	0.0040 (12)	0.0062 (12)	−0.0007 (12)
N2	0.0338 (13)	0.0367 (15)	0.0303 (13)	−0.0032 (12)	0.0056 (11)	0.0012 (11)
C2	0.0248 (14)	0.0316 (16)	0.0318 (16)	0.0011 (12)	0.0060 (12)	−0.0030 (13)
C3	0.0288 (15)	0.0372 (18)	0.0385 (17)	0.0001 (14)	0.0091 (13)	0.0015 (14)
C4	0.048 (2)	0.055 (2)	0.0389 (18)	−0.0089 (18)	0.0085 (15)	0.0046 (17)
C5	0.055 (2)	0.056 (2)	0.047 (2)	−0.0071 (19)	0.0200 (17)	0.0099 (17)
C6	0.0402 (18)	0.044 (2)	0.063 (2)	−0.0105 (16)	0.0172 (17)	0.0022 (17)
C7	0.0375 (17)	0.040 (2)	0.0473 (19)	−0.0061 (14)	0.0072 (15)	−0.0042 (15)
C8	0.0269 (14)	0.0323 (16)	0.0396 (17)	0.0013 (13)	0.0078 (13)	0.0010 (14)
C9	0.0300 (15)	0.0366 (17)	0.0291 (15)	−0.0015 (13)	0.0044 (12)	−0.0061 (13)
C10	0.0360 (17)	0.046 (2)	0.0330 (16)	0.0044 (15)	0.0031 (13)	0.0006 (14)
C11	0.0505 (19)	0.047 (2)	0.0308 (16)	−0.0025 (18)	−0.0009 (14)	0.0038 (15)
C12	0.055 (2)	0.042 (2)	0.0324 (17)	−0.0073 (17)	0.0142 (15)	−0.0029 (15)
S1	0.0570 (5)	0.0428 (5)	0.0438 (5)	0.0106 (4)	0.0232 (4)	0.0033 (4)
C13	0.0260 (14)	0.0321 (16)	0.0291 (15)	0.0027 (12)	0.0047 (12)	−0.0037 (12)
C14	0.0336 (15)	0.0342 (17)	0.0335 (16)	−0.0013 (14)	0.0033 (12)	−0.0004 (14)
C15	0.0370 (17)	0.0301 (17)	0.0419 (18)	−0.0018 (14)	0.0127 (14)	0.0007 (14)
C16	0.0372 (17)	0.0347 (18)	0.0457 (19)	−0.0061 (14)	0.0079 (14)	−0.0068 (15)
S2	0.0461 (5)	0.0469 (5)	0.0305 (4)	−0.0124 (4)	0.0015 (3)	−0.0007 (4)

Geometric parameters (Å, º)

N1—C1	1.314 (4)	C9—C10	1.353 (4)
N1—C8	1.366 (4)	C9—S1	1.712 (3)
C1—C2	1.440 (4)	C10—C11	1.417 (4)
C1—C9	1.476 (4)	C10—H10A	0.9300
N2—C2	1.317 (4)	C11—C12	1.338 (5)
N2—C3	1.361 (4)	C11—H11A	0.9300
C2—C13	1.468 (4)	C12—S1	1.700 (3)
C3—C8	1.400 (4)	C12—H12A	0.9300
C3—C4	1.407 (4)	C13—C14	1.370 (4)
C4—C5	1.356 (5)	C13—S2	1.726 (3)
C4—H4A	0.9300	C14—C15	1.404 (4)
C5—C6	1.406 (5)	C14—H14A	0.9300
C5—H5A	0.9300	C15—C16	1.346 (4)
C6—C7	1.356 (4)	C15—H15A	0.9300
C6—H6A	0.9300	C16—S2	1.705 (3)
C7—C8	1.406 (4)	C16—H16A	0.9300
C7—H7A	0.9300
C1—N1—C8	117.8 (2)	C10—C9—C1	129.5 (3)
N1—C1—C2	121.4 (3)	C10—C9—S1	110.9 (2)
N1—C1—C9	115.4 (2)	C1—C9—S1	119.6 (2)
C2—C1—C9	123.1 (3)	C9—C10—C11	112.5 (3)
C2—N2—C3	117.8 (2)	C9—C10—H10A	123.7
N2—C2—C1	121.0 (3)	C11—C10—H10A	123.7
N2—C2—C13	115.7 (2)	C12—C11—C10	112.8 (3)
C1—C2—C13	123.3 (3)	C12—C11—H11A	123.6
N2—C3—C8	121.3 (3)	C10—C11—H11A	123.6
N2—C3—C4	119.6 (3)	C11—C12—S1	111.8 (2)
C8—C3—C4	119.1 (3)	C11—C12—H12A	124.1
C5—C4—C3	120.3 (3)	S1—C12—H12A	124.1
C5—C4—H4A	119.8	C12—S1—C9	91.96 (16)
C3—C4—H4A	119.8	C14—C13—C2	133.0 (3)
C4—C5—C6	120.4 (3)	C14—C13—S2	110.0 (2)
C4—C5—H5A	119.8	C2—C13—S2	117.0 (2)
C6—C5—H5A	119.8	C13—C14—C15	113.2 (3)
C7—C6—C5	120.6 (3)	C13—C14—H14A	123.4
C7—C6—H6A	119.7	C15—C14—H14A	123.4
C5—C6—H6A	119.7	C16—C15—C14	113.0 (3)
C6—C7—C8	119.8 (3)	C16—C15—H15A	123.5
C6—C7—H7A	120.1	C14—C15—H15A	123.5
C8—C7—H7A	120.1	C15—C16—S2	111.8 (2)
N1—C8—C3	120.7 (3)	C15—C16—H16A	124.1
N1—C8—C7	119.5 (3)	S2—C16—H16A	124.1
C3—C8—C7	119.8 (3)	C16—S2—C13	92.06 (15)