2,5-Bis(4-tert-butyl­phen­yl)-3,4-dinitro­thio­phene

Huang, P.-H.; Cheng, Y.-D.; Wen, Y.-S.; Yeh, M.-C.P.; Lin, J.T.

doi:10.1107/S1600536805026097

2,5-Bis(4-tert-butylphenyl)-3,4-dinitrothiophene

P.-H. Huang, Y.-D. Cheng, Y.-S. Wen, M.-C. P. Yeh and J. T. Lin

The title compound, C₂₄H₂₆N₂O₄S, is a precursor for the production of low band gap conjugated polymers. The dihedral angles between the thiophene and benzene rings are 31.5 (1) and 52.2 (1)°, and that between the two benzene rings is 35.7 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026097/ob6565sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026097/ob6565Isup2.hkl Contains datablock I

CCDC reference: 287675

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.030
wR factor = 0.077
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), has been shown to be an excellent precursor for the production of low band gap conjugated polymers and organic light-emitting devices, etc. As indicated in the scheme, standard procedures were administrated to synthesize (I) in high yield.

The molecular structure is shown in Fig. 1. The double bonds and C—C single bond of (I) are slightly shorter than those of the parent thiophene, while the S—C single bond is slightly elongated (Bak et al., 1961). The dihedral angles between the thiophene (S/C2–C5) and benzene rings (C11–C16 and C21–C26) are 52.2 (1) and 31.5 (1)°, respectively, and that between the two benzene rings is 35.7 (1)°.

Experimental top

Compound (I) was prepared via several synthetic steps, such as bromination, nitration and a palladium-catalyzed aromatic Still-coupling reaction (see scheme). The compound is soluble in appropriate organic solvents and was considerably purified by column chromatography (Thomas et al., 2002). The compound was synthesized by the following procedure. A two-necked round-bottomed flask was charged with Pd(PPh₃)₂Cl₂ (140 mg), tributyl(4-tert-butylphenyl)stannane (9.3 g, 22 mmol), 2,5-dibromo-3,4-dinitrothiophene (3.32 g, 10 mmol) and DMF (20 ml), and the reaction mixture stirred under nitrogen and heated at 343 K for 16 h. After cooling, the mixture was diluted with ether and the organic phase was washed with water and brine. After drying over anhydrous MgSO₄ and removing the volatiles, the residue was purified by column chromatography using CH₂Cl₂/n-hexane as eluent and followed by recrystallization from CH₂Cl₂ and MeOH to yield 2.4 g (60%) of (I) as a pale-yellow solid. Crystals suitable for X-ray diffraction were grown from a CH₂Cl₂ solution layered with hexane at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

2,5-Bis(4-tert-butylphenyl)-3,4-dinitrothiophene top

Crystal data top

C₂₄H₂₆N₂O₄S	F(000) = 928
M_r = 438.53	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7514 reflections
a = 14.026 (3) Å	θ = 2.9–31.2°
b = 11.120 (2) Å	µ = 0.18 mm⁻¹
c = 14.491 (3) Å	T = 100 K
β = 99.349 (9)°	Prism, yellow
V = 2230.2 (8) Å³	0.32 × 0.24 × 0.2 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3530 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ϕ and ω scans	h = −12→16
32280 measured reflections	k = −13→13
3915 independent reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0326P)² + 1.2009P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3915 reflections	Δρ_max = 0.22 e Å⁻³
281 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (5)

Crystal data top

C₂₄H₂₆N₂O₄S	V = 2230.2 (8) Å³
M_r = 438.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.026 (3) Å	µ = 0.18 mm⁻¹
b = 11.120 (2) Å	T = 100 K
c = 14.491 (3) Å	0.32 × 0.24 × 0.2 mm
β = 99.349 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3530 reflections with I > 2σ(I)
32280 measured reflections	R_int = 0.025
3915 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
3915 reflections	Δρ_min = −0.23 e Å⁻³
281 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S	0.14983 (2)	0.08831 (3)	0.58157 (2)	0.01804 (11)
O1	0.31389 (7)	−0.06073 (10)	0.36082 (7)	0.0294 (3)
O2	0.16866 (8)	−0.06315 (10)	0.28221 (7)	0.0295 (3)
O3	0.11336 (8)	0.18529 (11)	0.26159 (7)	0.0332 (3)
O4	−0.02213 (8)	0.10858 (11)	0.28763 (8)	0.0349 (3)
N3	0.22802 (8)	−0.03514 (10)	0.35079 (8)	0.0201 (3)
N4	0.06309 (9)	0.13440 (11)	0.31079 (8)	0.0225 (3)
C2	0.22356 (9)	0.01059 (12)	0.51825 (9)	0.0168 (3)
C3	0.19237 (10)	0.03018 (12)	0.42469 (9)	0.0175 (3)
C4	0.10854 (10)	0.10342 (12)	0.40599 (9)	0.0181 (3)
C5	0.07559 (9)	0.14406 (12)	0.48364 (9)	0.0182 (3)
C11	0.30055 (10)	−0.06503 (12)	0.57029 (9)	0.0166 (3)
C12	0.39619 (10)	−0.05294 (13)	0.55743 (10)	0.0204 (3)
H12	0.4119	0.0004	0.5110	0.024*
C13	0.46855 (10)	−0.11787 (13)	0.61171 (10)	0.0205 (3)
H13	0.5334	−0.1080	0.6017	0.025*
C14	0.44934 (9)	−0.19708 (12)	0.68036 (9)	0.0169 (3)
C15	0.35282 (10)	−0.21019 (12)	0.69175 (9)	0.0186 (3)
H15	0.3371	−0.2651	0.7372	0.022*
C16	0.27962 (10)	−0.14511 (12)	0.63845 (9)	0.0180 (3)
H16	0.2148	−0.1550	0.6483	0.022*
C17	0.52959 (10)	−0.26877 (12)	0.74022 (10)	0.0194 (3)
C18	0.63043 (10)	−0.22355 (14)	0.72934 (11)	0.0250 (3)
H18A	0.6384	−0.2290	0.6635	0.037*
H18B	0.6796	−0.2731	0.7675	0.037*
H18C	0.6377	−0.1397	0.7500	0.037*
C19	0.52019 (10)	−0.25867 (13)	0.84402 (10)	0.0234 (3)
H19A	0.5721	−0.3047	0.8817	0.035*
H19B	0.4574	−0.2908	0.8535	0.035*
H19C	0.5251	−0.1740	0.8631	0.035*
C20	0.52005 (11)	−0.40104 (13)	0.70881 (11)	0.0253 (3)
H20A	0.5259	−0.4066	0.6425	0.038*
H20B	0.4569	−0.4321	0.7180	0.038*
H20C	0.5713	−0.4487	0.7459	0.038*
C21	−0.00364 (10)	0.22648 (12)	0.49495 (10)	0.0183 (3)
C22	−0.05037 (10)	0.21570 (13)	0.57232 (9)	0.0190 (3)
H22	−0.0314	0.1541	0.6170	0.023*
C23	−0.12390 (10)	0.29344 (12)	0.58488 (10)	0.0193 (3)
H23	−0.1550	0.2838	0.6379	0.023*
C24	−0.15370 (10)	0.38585 (12)	0.52166 (10)	0.0191 (3)
C25	−0.10578 (10)	0.39718 (13)	0.44527 (10)	0.0227 (3)
H25	−0.1238	0.4599	0.4014	0.027*
C26	−0.03232 (10)	0.31915 (13)	0.43164 (10)	0.0226 (3)
H26	−0.0012	0.3289	0.3786	0.027*
C27	−0.23583 (10)	0.46944 (13)	0.53889 (10)	0.0238 (3)
C28	−0.20964 (12)	0.52867 (15)	0.63508 (12)	0.0339 (4)
H28A	−0.2623	0.5819	0.6462	0.051*
H28B	−0.1502	0.5757	0.6371	0.051*
H28C	−0.1996	0.4664	0.6835	0.051*
C29	−0.32802 (11)	0.39450 (15)	0.53742 (12)	0.0309 (4)
H29A	−0.3812	0.4472	0.5481	0.046*
H29B	−0.3170	0.3334	0.5867	0.046*
H29C	−0.3448	0.3550	0.4765	0.046*
C30	−0.25536 (13)	0.56730 (17)	0.46464 (14)	0.0432 (5)
H30A	−0.3085	0.6184	0.4776	0.065*
H30B	−0.2729	0.5301	0.4029	0.065*
H30C	−0.1971	0.6163	0.4656	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.01659 (18)	0.02116 (19)	0.01617 (19)	0.00389 (13)	0.00204 (13)	−0.00043 (13)
O1	0.0225 (6)	0.0372 (6)	0.0295 (6)	0.0079 (5)	0.0074 (4)	−0.0052 (5)
O2	0.0324 (6)	0.0372 (6)	0.0176 (5)	0.0020 (5)	0.0000 (5)	−0.0055 (5)
O3	0.0313 (6)	0.0436 (7)	0.0252 (6)	−0.0008 (5)	0.0060 (5)	0.0131 (5)
O4	0.0216 (6)	0.0542 (8)	0.0260 (6)	−0.0051 (5)	−0.0051 (4)	0.0026 (5)
N3	0.0241 (7)	0.0192 (6)	0.0175 (6)	0.0010 (5)	0.0044 (5)	0.0015 (5)
N4	0.0222 (6)	0.0253 (7)	0.0196 (6)	0.0026 (5)	0.0015 (5)	0.0018 (5)
C2	0.0157 (7)	0.0156 (7)	0.0195 (7)	−0.0016 (5)	0.0042 (5)	−0.0013 (5)
C3	0.0172 (7)	0.0173 (7)	0.0185 (7)	−0.0006 (5)	0.0043 (5)	−0.0012 (6)
C4	0.0165 (7)	0.0199 (7)	0.0171 (7)	−0.0008 (5)	0.0007 (5)	0.0015 (6)
C5	0.0155 (7)	0.0188 (7)	0.0196 (7)	−0.0014 (5)	0.0012 (5)	0.0012 (6)
C11	0.0176 (7)	0.0156 (7)	0.0161 (7)	0.0006 (5)	0.0013 (5)	−0.0028 (5)
C12	0.0203 (7)	0.0212 (7)	0.0206 (7)	−0.0003 (6)	0.0061 (6)	0.0040 (6)
C13	0.0151 (7)	0.0234 (8)	0.0240 (8)	0.0006 (6)	0.0060 (6)	0.0024 (6)
C14	0.0181 (7)	0.0137 (7)	0.0188 (7)	0.0009 (5)	0.0030 (5)	−0.0022 (5)
C15	0.0211 (7)	0.0162 (7)	0.0188 (7)	−0.0019 (6)	0.0048 (5)	0.0017 (5)
C16	0.0157 (7)	0.0189 (7)	0.0202 (7)	−0.0006 (5)	0.0049 (5)	−0.0010 (6)
C17	0.0179 (7)	0.0170 (7)	0.0230 (7)	0.0020 (6)	0.0027 (6)	0.0018 (6)
C18	0.0182 (7)	0.0263 (8)	0.0300 (8)	0.0051 (6)	0.0028 (6)	0.0043 (7)
C19	0.0219 (7)	0.0241 (8)	0.0233 (8)	0.0032 (6)	0.0008 (6)	0.0020 (6)
C20	0.0282 (8)	0.0177 (7)	0.0291 (8)	0.0051 (6)	0.0024 (6)	0.0010 (6)
C21	0.0139 (6)	0.0202 (7)	0.0202 (7)	−0.0004 (5)	0.0008 (5)	−0.0016 (6)
C22	0.0187 (7)	0.0192 (7)	0.0179 (7)	0.0001 (6)	−0.0002 (5)	0.0006 (6)
C23	0.0183 (7)	0.0215 (7)	0.0181 (7)	−0.0006 (6)	0.0034 (5)	−0.0023 (6)
C24	0.0150 (7)	0.0192 (7)	0.0219 (7)	−0.0007 (5)	−0.0004 (5)	−0.0032 (6)
C25	0.0205 (7)	0.0230 (8)	0.0237 (8)	0.0030 (6)	0.0010 (6)	0.0038 (6)
C26	0.0196 (7)	0.0270 (8)	0.0218 (7)	0.0013 (6)	0.0054 (6)	0.0038 (6)
C27	0.0196 (7)	0.0232 (8)	0.0283 (8)	0.0047 (6)	0.0029 (6)	−0.0013 (6)
C28	0.0268 (8)	0.0309 (9)	0.0433 (10)	0.0054 (7)	0.0034 (7)	−0.0144 (8)
C29	0.0182 (8)	0.0359 (9)	0.0385 (9)	0.0037 (7)	0.0037 (7)	−0.0102 (7)
C30	0.0404 (10)	0.0411 (10)	0.0514 (12)	0.0241 (8)	0.0170 (9)	0.0162 (9)

Geometric parameters (Å, º) top

S—C2	1.7224 (14)	C19—H19A	0.9800
S—C5	1.7327 (14)	C19—H19B	0.9800
O1—N3	1.2231 (15)	C19—H19C	0.9800
O2—N3	1.2284 (15)	C20—H20A	0.9800
O3—N4	1.2202 (16)	C20—H20B	0.9800
O4—N4	1.2220 (16)	C20—H20C	0.9800
N3—C3	1.4486 (18)	C21—C22	1.393 (2)
N4—C4	1.4638 (18)	C21—C26	1.395 (2)
C2—C3	1.3727 (19)	C22—C23	1.380 (2)
C2—C11	1.4755 (19)	C22—H22	0.9500
C3—C4	1.4198 (19)	C23—C24	1.395 (2)
C4—C5	1.361 (2)	C23—H23	0.9500
C5—C21	1.4699 (19)	C24—C25	1.391 (2)
C11—C12	1.391 (2)	C24—C27	1.5319 (19)
C11—C16	1.3961 (19)	C25—C26	1.385 (2)
C12—C13	1.382 (2)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.3875 (19)	C27—C30	1.524 (2)
C13—H13	0.9500	C27—C28	1.531 (2)
C14—C15	1.3977 (19)	C27—C29	1.536 (2)
C14—C17	1.5290 (19)	C28—H28A	0.9800
C15—C16	1.3844 (19)	C28—H28B	0.9800
C15—H15	0.9500	C28—H28C	0.9800
C16—H16	0.9500	C29—H29A	0.9800
C17—C18	1.5333 (19)	C29—H29B	0.9800
C17—C19	1.535 (2)	C29—H29C	0.9800
C17—C20	1.539 (2)	C30—H30A	0.9800
C18—H18A	0.9800	C30—H30B	0.9800
C18—H18B	0.9800	C30—H30C	0.9800
C18—H18C	0.9800

C2—S—C5	94.37 (7)	C17—C19—H19C	109.5
O1—N3—O2	124.20 (12)	H19A—C19—H19C	109.5
O1—N3—C3	118.70 (11)	H19B—C19—H19C	109.5
O2—N3—C3	117.08 (12)	C17—C20—H20A	109.5
O3—N4—O4	125.50 (12)	C17—C20—H20B	109.5
O3—N4—C4	117.09 (12)	H20A—C20—H20B	109.5
O4—N4—C4	117.40 (12)	C17—C20—H20C	109.5
C3—C2—C11	133.20 (12)	H20A—C20—H20C	109.5
C3—C2—S	108.90 (10)	H20B—C20—H20C	109.5
C11—C2—S	117.81 (10)	C22—C21—C26	118.03 (13)
C2—C3—C4	113.62 (12)	C22—C21—C5	119.95 (12)
C2—C3—N3	123.90 (12)	C26—C21—C5	121.99 (13)
C4—C3—N3	121.41 (12)	C23—C22—C21	120.77 (13)
C5—C4—C3	114.49 (12)	C23—C22—H22	119.6
C5—C4—N4	123.14 (12)	C21—C22—H22	119.6
C3—C4—N4	122.36 (12)	C22—C23—C24	121.70 (13)
C4—C5—C21	131.57 (13)	C22—C23—H23	119.1
C4—C5—S	108.58 (10)	C24—C23—H23	119.1
C21—C5—S	119.75 (10)	C25—C24—C23	117.22 (13)
C12—C11—C16	118.34 (12)	C25—C24—C27	123.24 (13)
C12—C11—C2	121.22 (12)	C23—C24—C27	119.54 (13)
C16—C11—C2	120.30 (12)	C26—C25—C24	121.56 (13)
C13—C12—C11	120.56 (13)	C26—C25—H25	119.2
C13—C12—H12	119.7	C24—C25—H25	119.2
C11—C12—H12	119.7	C25—C26—C21	120.70 (13)
C12—C13—C14	121.97 (13)	C25—C26—H26	119.6
C12—C13—H13	119.0	C21—C26—H26	119.6
C14—C13—H13	119.0	C30—C27—C28	108.95 (14)
C13—C14—C15	117.10 (12)	C30—C27—C24	111.84 (12)
C13—C14—C17	121.80 (12)	C28—C27—C24	109.50 (12)
C15—C14—C17	121.09 (12)	C30—C27—C29	108.87 (13)
C16—C15—C14	121.62 (13)	C28—C27—C29	108.84 (13)
C16—C15—H15	119.2	C24—C27—C29	108.79 (12)
C14—C15—H15	119.2	C27—C28—H28A	109.5
C15—C16—C11	120.40 (12)	C27—C28—H28B	109.5
C15—C16—H16	119.8	H28A—C28—H28B	109.5
C11—C16—H16	119.8	C27—C28—H28C	109.5
C14—C17—C18	112.15 (12)	H28A—C28—H28C	109.5
C14—C17—C19	110.20 (11)	H28B—C28—H28C	109.5
C18—C17—C19	107.71 (12)	C27—C29—H29A	109.5
C14—C17—C20	108.06 (11)	C27—C29—H29B	109.5
C18—C17—C20	108.68 (12)	H29A—C29—H29B	109.5
C19—C17—C20	110.03 (12)	C27—C29—H29C	109.5
C17—C18—H18A	109.5	H29A—C29—H29C	109.5
C17—C18—H18B	109.5	H29B—C29—H29C	109.5
H18A—C18—H18B	109.5	C27—C30—H30A	109.5
C17—C18—H18C	109.5	C27—C30—H30B	109.5
H18A—C18—H18C	109.5	H30A—C30—H30B	109.5
H18B—C18—H18C	109.5	C27—C30—H30C	109.5
C17—C19—H19A	109.5	H30A—C30—H30C	109.5
C17—C19—H19B	109.5	H30B—C30—H30C	109.5
H19A—C19—H19B	109.5

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₂O₄S
M_r	438.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.026 (3), 11.120 (2), 14.491 (3)
β (°)	99.349 (9)
V (Å³)	2230.2 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.32 × 0.24 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	32280, 3915, 3530
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.04
No. of reflections	3915
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

S—C2	1.7224 (14)	C3—C4	1.4198 (19)
S—C5	1.7327 (14)	C4—C5	1.361 (2)
C2—C3	1.3727 (19)

C2—S—C5	94.37 (7)	C2—C3—C4	113.62 (12)
C3—C2—S	108.90 (10)	C5—C4—C3	114.49 (12)

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Format		BIBTeX
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		CIF
		SGML
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		Plain Text

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2,5-Bis(4-tert-butyl­phen­yl)-3,4-dinitro­thio­phene

Supporting information

Key indicators

checkCIF/PLATON results

2,5-Bis(4-tert-butylphenyl)-3,4-dinitrothiophene