3,4-Dinitro-N,N,N′,N′-tetra­phenyl­thio­phene-2,5-diamine

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

doi:10.1107/S1600536805029120

3,4-Dinitro-N,N,N',N'-tetraphenylthiophene-2,5-diamine

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

The title compound, C₂₈H₂₀N₄O₄S, studied with X-ray crystallography, NMR, mass spectrometry and elemental analysis, is presented. The two C=C double bonds are slightly shorter than those of the parent thiophene, while the C-C single bond is slightly elongated.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029120/ww6424sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029120/ww6424Isup2.hkl Contains datablock I

CCDC reference: 287757

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.101
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.65

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   0 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 (OLEDs) (Thomas et al., 2002 or 2000?), etc. Standard procedures including bromination, nitration and a palladium catalysed aromatic C—N coupling reaction were used to synthesize the donor–π-acceptor-type compound, (I), in high yield (see scheme). The compound is soluble in organic solvents and was considerably purified by column chromatography.

The structure can be regarded as consisting of alternating (010) layers. X-ray data show that the double bonds of (I) are shorter [C2—C3 = 1.353 (3) Å] than those of the parent thiophene [C2—C3 = 1.370 (2) Å], while the C—C single bond is slightly elongated [C3—C4 = 1.425 (3) Å] compared with the parent thiophene [C3—C4 = 1.423 (2) Å] (Bak et al., 1961). This bond localization in (I) can be attributed to the donor–π-acceptor nature of the substituents, as well as steric repulsion between the two NO₂ groups.

Experimental top

A two-necked round-bottomed flask was charged with Pd(OAc)₂ (1 mmol% per halogen atom), t-BuONa (1.2 equivalents per halogen atom), 2,5-dibromo-3,4-dinitrothiophene (1.66 g, 5 mmol) and diphenylamine (1.68 g, 10 mmol). Dry toluene was added and the reaction mixture was stirred under nitrogen for 10 min. Tri-tert-butylphosphine (2 mmol%) in dry toluene was added through a syringe (1.0 mmol of the phosphine in 1 ml of dry toluene). The reaction mixture was heated at 363 K for 20 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, followed by recrystallization from CH₂Cl₂ and MeOH. Crystals suitable for single-crystal X-ray diffraction were grown from a CH₂Cl₂ solution layered with hexane at room temperature. The compound was obtained as a red solid in 79% yield. FAB MS: m/e 509 (M+H)⁺; ¹H NMR (CDCl₃): δ 7.09 (d, J = 7.7 Hz, 8H, ortho-C₆H₅), 7.15 (t, J = 7.3 Hz, 4H, para-C₆H₅), 7.31 (t, J = 7.7 Hz, 8H, meta-C₆H₅). Analysis calculated for C₂₈H₂₀N₄O₄S: C 66.13, H 3.96, N 11.02%; found: C 66.35, H 3.67, N 11.42%.

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), drawn with 30% probability displacement ellipsoids, showing the atom-numbering scheme. H atoms are shown as small spheres of the arbitrary radii.
	Fig. 2. Packing diagram for (I), viewed along the c axis. H atoms have been omitted for clarity.

3,4-Dinitro-N,N,N',N'-tetraphenylthiophene-2,5-diamine top

Crystal data top

C₂₈H₂₀N₄O₄S	F(000) = 1056
M_r = 508.54	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3556 reflections
a = 9.9075 (4) Å	θ = 2.2–24.7°
b = 19.0621 (7) Å	µ = 0.18 mm⁻¹
c = 13.5418 (5) Å	T = 100 K
β = 108.977 (2)°	Prism, red
V = 2418.47 (16) Å³	0.34 × 0.2 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3379 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.0°, θ_min = 1.9°
ϕ and ω scans	h = −11→11
22681 measured reflections	k = −22→22
4264 independent reflections	l = −16→16

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0352P)² + 1.644P] where P = (F_o² + 2F_c²)/3
4264 reflections	(Δ/σ)_max < 0.001
335 parameters	Δρ_max = 0.92 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₈H₂₀N₄O₄S	V = 2418.47 (16) Å³
M_r = 508.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9075 (4) Å	µ = 0.18 mm⁻¹
b = 19.0621 (7) Å	T = 100 K
c = 13.5418 (5) Å	0.34 × 0.2 × 0.18 mm
β = 108.977 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3379 reflections with I > 2σ(I)
22681 measured reflections	R_int = 0.035
4264 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.07	Δρ_max = 0.92 e Å⁻³
4264 reflections	Δρ_min = −0.20 e Å⁻³
335 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	0.14386 (5)	0.19726 (3)	0.76901 (4)	0.02571 (15)
O1	−0.16195 (18)	0.07572 (9)	0.49648 (12)	0.0418 (4)
O2	−0.25881 (16)	0.17939 (9)	0.46885 (12)	0.0389 (4)
O3	−0.04222 (15)	0.22456 (8)	0.39982 (10)	0.0307 (4)
O4	0.02078 (15)	0.32747 (8)	0.46971 (11)	0.0296 (3)
N1	−0.04938 (17)	0.08972 (9)	0.73135 (12)	0.0238 (4)
N2	0.22500 (17)	0.31126 (9)	0.68470 (12)	0.0249 (4)
N3	−0.16109 (18)	0.13903 (10)	0.51226 (13)	0.0298 (4)
N4	0.00092 (17)	0.26419 (9)	0.47562 (12)	0.0252 (4)
C2	0.0095 (2)	0.14329 (11)	0.68913 (15)	0.0244 (4)
C3	−0.0360 (2)	0.16880 (11)	0.59051 (15)	0.0239 (4)
C4	0.0306 (2)	0.23258 (11)	0.57656 (15)	0.0239 (4)
C5	0.1320 (2)	0.25544 (11)	0.66699 (15)	0.0243 (4)
C11	0.0377 (2)	0.03035 (11)	0.77337 (15)	0.0249 (5)
C12	0.1261 (2)	0.00357 (11)	0.72125 (17)	0.0305 (5)
H12	0.1280	0.0244	0.6596	0.037*
C13	0.2113 (2)	−0.05411 (12)	0.76083 (19)	0.0383 (6)
H13	0.2707	−0.0718	0.7259	0.046*
C14	0.2086 (2)	−0.08574 (12)	0.85264 (19)	0.0392 (6)
H14	0.2650	−0.1249	0.8787	0.047*
C15	0.1217 (2)	−0.05877 (12)	0.90469 (18)	0.0359 (5)
H15	0.1199	−0.0798	0.9662	0.043*
C16	0.0369 (2)	−0.00044 (11)	0.86619 (16)	0.0296 (5)
H16	−0.0203	0.0179	0.9024	0.036*
C21	−0.1906 (2)	0.09890 (11)	0.73584 (14)	0.0237 (4)
C22	−0.2775 (2)	0.04147 (11)	0.73164 (16)	0.0291 (5)
H22	−0.2444	−0.0035	0.7256	0.035*
C23	−0.4142 (2)	0.05095 (13)	0.73643 (17)	0.0353 (5)
H23	−0.4717	0.0121	0.7347	0.042*
C24	−0.4656 (2)	0.11735 (13)	0.74366 (17)	0.0372 (6)
H24	−0.5575	0.1236	0.7463	0.045*
C25	−0.3783 (2)	0.17457 (13)	0.74696 (16)	0.0366 (6)
H25	−0.4120	0.2195	0.7519	0.044*
C26	−0.2420 (2)	0.16574 (12)	0.74300 (16)	0.0299 (5)
H26	−0.1845	0.2046	0.7451	0.036*
C31	0.2976 (2)	0.32895 (11)	0.61243 (15)	0.0255 (5)
C32	0.3075 (2)	0.39877 (12)	0.58713 (17)	0.0322 (5)
H32	0.2633	0.4333	0.6143	0.039*
C33	0.3831 (2)	0.41685 (14)	0.52137 (18)	0.0399 (6)
H33	0.3897	0.4637	0.5041	0.048*
C34	0.4487 (2)	0.36574 (15)	0.48128 (17)	0.0431 (6)
H34	0.5011	0.3782	0.4382	0.052*
C35	0.4367 (2)	0.29610 (14)	0.50493 (17)	0.0397 (6)
H35	0.4802	0.2617	0.4770	0.048*
C36	0.3600 (2)	0.27719 (12)	0.57014 (16)	0.0302 (5)
H36	0.3507	0.2302	0.5853	0.036*
C41	0.2608 (2)	0.34701 (10)	0.78325 (15)	0.0246 (5)
C42	0.1535 (2)	0.36635 (11)	0.82214 (15)	0.0262 (5)
H42	0.0590	0.3561	0.7845	0.031*
C43	0.1864 (2)	0.40100 (11)	0.91718 (16)	0.0313 (5)
H43	0.1140	0.4133	0.9437	0.038*
C44	0.3260 (2)	0.41720 (12)	0.97213 (17)	0.0352 (5)
H44	0.3477	0.4410	1.0353	0.042*
C45	0.4345 (2)	0.39822 (12)	0.93385 (17)	0.0354 (5)
H45	0.5286	0.4093	0.9713	0.042*
C46	0.4026 (2)	0.36245 (11)	0.83927 (17)	0.0304 (5)
H46	0.4753	0.3490	0.8138	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0252 (3)	0.0284 (3)	0.0194 (3)	−0.0028 (2)	0.0016 (2)	0.0007 (2)
O1	0.0513 (11)	0.0346 (10)	0.0329 (9)	−0.0152 (8)	0.0046 (8)	−0.0054 (7)
O2	0.0239 (8)	0.0535 (11)	0.0327 (9)	−0.0010 (8)	−0.0001 (7)	0.0047 (8)
O3	0.0354 (8)	0.0337 (9)	0.0206 (7)	−0.0046 (7)	0.0058 (6)	−0.0036 (7)
O4	0.0307 (8)	0.0261 (9)	0.0290 (8)	−0.0023 (6)	0.0055 (6)	0.0045 (6)
N1	0.0226 (9)	0.0235 (9)	0.0252 (9)	0.0011 (7)	0.0075 (7)	0.0034 (7)
N2	0.0238 (9)	0.0262 (10)	0.0231 (9)	−0.0054 (7)	0.0053 (7)	−0.0037 (7)
N3	0.0275 (10)	0.0383 (12)	0.0213 (9)	−0.0070 (9)	0.0048 (8)	0.0008 (8)
N4	0.0209 (9)	0.0307 (11)	0.0223 (9)	−0.0004 (7)	0.0048 (7)	0.0014 (8)
C2	0.0215 (10)	0.0262 (11)	0.0239 (10)	−0.0013 (9)	0.0053 (8)	−0.0014 (9)
C3	0.0207 (10)	0.0269 (11)	0.0213 (10)	−0.0014 (8)	0.0029 (8)	−0.0027 (8)
C4	0.0223 (10)	0.0266 (11)	0.0215 (10)	0.0004 (8)	0.0052 (8)	0.0021 (8)
C5	0.0231 (10)	0.0273 (11)	0.0220 (10)	0.0011 (9)	0.0066 (8)	0.0000 (9)
C11	0.0198 (10)	0.0249 (11)	0.0251 (10)	−0.0025 (8)	0.0007 (8)	−0.0001 (9)
C12	0.0253 (11)	0.0336 (13)	0.0310 (11)	0.0012 (9)	0.0071 (9)	0.0020 (10)
C13	0.0254 (12)	0.0394 (14)	0.0480 (14)	0.0053 (10)	0.0090 (10)	−0.0042 (11)
C14	0.0271 (12)	0.0323 (13)	0.0466 (14)	0.0051 (10)	−0.0041 (10)	0.0022 (11)
C15	0.0344 (13)	0.0345 (13)	0.0314 (12)	−0.0019 (10)	0.0004 (10)	0.0067 (10)
C16	0.0273 (11)	0.0313 (12)	0.0262 (11)	−0.0002 (9)	0.0032 (9)	0.0011 (9)
C21	0.0248 (10)	0.0285 (12)	0.0162 (9)	0.0022 (9)	0.0042 (8)	0.0001 (8)
C22	0.0262 (11)	0.0294 (12)	0.0309 (11)	0.0023 (9)	0.0084 (9)	0.0026 (9)
C23	0.0278 (12)	0.0423 (14)	0.0348 (12)	−0.0009 (10)	0.0091 (10)	0.0103 (10)
C24	0.0279 (12)	0.0570 (16)	0.0270 (12)	0.0122 (11)	0.0095 (9)	0.0051 (11)
C25	0.0345 (13)	0.0418 (14)	0.0287 (12)	0.0137 (11)	0.0036 (10)	−0.0043 (10)
C26	0.0283 (11)	0.0308 (12)	0.0255 (11)	0.0036 (9)	0.0020 (9)	−0.0012 (9)
C31	0.0200 (10)	0.0320 (12)	0.0208 (10)	−0.0032 (9)	0.0016 (8)	−0.0002 (9)
C32	0.0252 (11)	0.0323 (13)	0.0365 (12)	−0.0026 (9)	0.0063 (9)	0.0013 (10)
C33	0.0315 (13)	0.0467 (15)	0.0379 (13)	−0.0112 (11)	0.0062 (10)	0.0103 (11)
C34	0.0279 (12)	0.074 (2)	0.0240 (12)	−0.0146 (13)	0.0040 (10)	−0.0012 (12)
C35	0.0272 (12)	0.0619 (18)	0.0281 (12)	−0.0036 (11)	0.0064 (10)	−0.0165 (11)
C36	0.0220 (11)	0.0358 (13)	0.0274 (11)	−0.0017 (9)	0.0005 (9)	−0.0071 (9)
C41	0.0281 (11)	0.0198 (11)	0.0219 (10)	−0.0021 (8)	0.0024 (8)	−0.0002 (8)
C42	0.0251 (11)	0.0251 (11)	0.0242 (10)	−0.0006 (9)	0.0023 (8)	0.0009 (9)
C43	0.0369 (13)	0.0286 (12)	0.0278 (11)	0.0043 (10)	0.0098 (10)	0.0017 (9)
C44	0.0413 (14)	0.0322 (13)	0.0249 (11)	0.0039 (10)	0.0008 (10)	−0.0044 (10)
C45	0.0276 (12)	0.0342 (13)	0.0327 (12)	0.0032 (10)	−0.0063 (9)	−0.0049 (10)
C46	0.0246 (11)	0.0289 (12)	0.0331 (12)	0.0036 (9)	0.0031 (9)	−0.0024 (9)

Geometric parameters (Å, º) top

S—C5	1.745 (2)	C22—H22	0.9300
S—C2	1.750 (2)	C23—C24	1.380 (3)
O1—N3	1.225 (2)	C23—H23	0.9300
O2—N3	1.227 (2)	C24—C25	1.384 (3)
O3—N4	1.234 (2)	C24—H24	0.9300
O4—N4	1.229 (2)	C25—C26	1.379 (3)
N1—C2	1.388 (3)	C25—H25	0.9300
N1—C11	1.425 (3)	C26—H26	0.9300
N1—C21	1.430 (3)	C31—C36	1.383 (3)
N2—C5	1.377 (3)	C31—C32	1.386 (3)
N2—C31	1.431 (3)	C32—C33	1.381 (3)
N2—C41	1.436 (2)	C32—H32	0.9300
N3—C3	1.458 (3)	C33—C34	1.377 (4)
N4—C4	1.434 (2)	C33—H33	0.9300
C2—C3	1.353 (3)	C34—C35	1.380 (4)
C3—C4	1.425 (3)	C34—H34	0.9300
C4—C5	1.378 (3)	C35—C36	1.387 (3)
C11—C12	1.388 (3)	C35—H35	0.9300
C11—C16	1.390 (3)	C36—H36	0.9300
C12—C13	1.384 (3)	C41—C42	1.381 (3)
C12—H12	0.9300	C41—C46	1.394 (3)
C13—C14	1.390 (3)	C42—C43	1.388 (3)
C13—H13	0.9300	C42—H42	0.9300
C14—C15	1.377 (3)	C43—C44	1.376 (3)
C14—H14	0.9300	C43—H43	0.9300
C15—C16	1.389 (3)	C44—C45	1.384 (3)
C15—H15	0.9300	C44—H44	0.9300
C16—H16	0.9300	C45—C46	1.394 (3)
C21—C22	1.383 (3)	C45—H45	0.9300
C21—C26	1.387 (3)	C46—H46	0.9300
C22—C23	1.389 (3)

C5—S—C2	92.43 (10)	C24—C23—C22	120.7 (2)
C2—N1—C11	117.87 (16)	C24—C23—H23	119.6
C2—N1—C21	118.39 (16)	C22—C23—H23	119.6
C11—N1—C21	123.63 (16)	C23—C24—C25	119.0 (2)
C5—N2—C31	121.33 (16)	C23—C24—H24	120.5
C5—N2—C41	118.54 (16)	C25—C24—H24	120.5
C31—N2—C41	119.76 (16)	C26—C25—C24	120.8 (2)
O1—N3—O2	125.07 (18)	C26—C25—H25	119.6
O1—N3—C3	117.79 (18)	C24—C25—H25	119.6
O2—N3—C3	117.12 (18)	C25—C26—C21	120.1 (2)
O4—N4—O3	124.50 (16)	C25—C26—H26	120.0
O4—N4—C4	119.14 (16)	C21—C26—H26	120.0
O3—N4—C4	116.35 (17)	C36—C31—C32	120.4 (2)
C3—C2—N1	128.37 (18)	C36—C31—N2	120.46 (19)
C3—C2—S	109.95 (15)	C32—C31—N2	119.15 (19)
N1—C2—S	120.99 (14)	C33—C32—C31	119.7 (2)
C2—C3—C4	114.66 (18)	C33—C32—H32	120.1
C2—C3—N3	120.60 (18)	C31—C32—H32	120.1
C4—C3—N3	123.81 (17)	C34—C33—C32	120.1 (2)
C5—C4—C3	112.78 (17)	C34—C33—H33	119.9
C5—C4—N4	125.34 (18)	C32—C33—H33	119.9
C3—C4—N4	121.64 (17)	C33—C34—C35	120.1 (2)
N2—C5—C4	130.73 (18)	C33—C34—H34	119.9
N2—C5—S	118.96 (14)	C35—C34—H34	119.9
C4—C5—S	110.15 (15)	C34—C35—C36	120.3 (2)
C12—C11—C16	119.65 (19)	C34—C35—H35	119.9
C12—C11—N1	119.29 (18)	C36—C35—H35	119.9
C16—C11—N1	121.06 (18)	C31—C36—C35	119.3 (2)
C13—C12—C11	120.1 (2)	C31—C36—H36	120.4
C13—C12—H12	119.9	C35—C36—H36	120.4
C11—C12—H12	119.9	C42—C41—C46	120.04 (19)
C12—C13—C14	120.3 (2)	C42—C41—N2	119.51 (18)
C12—C13—H13	119.9	C46—C41—N2	120.45 (18)
C14—C13—H13	119.9	C41—C42—C43	120.22 (19)
C15—C14—C13	119.6 (2)	C41—C42—H42	119.9
C15—C14—H14	120.2	C43—C42—H42	119.9
C13—C14—H14	120.2	C44—C43—C42	120.0 (2)
C14—C15—C16	120.6 (2)	C44—C43—H43	120.0
C14—C15—H15	119.7	C42—C43—H43	120.0
C16—C15—H15	119.7	C43—C44—C45	120.3 (2)
C11—C16—C15	119.8 (2)	C43—C44—H44	119.8
C11—C16—H16	120.1	C45—C44—H44	119.8
C15—C16—H16	120.1	C44—C45—C46	120.1 (2)
C22—C21—C26	119.48 (19)	C44—C45—H45	120.0
C22—C21—N1	120.40 (18)	C46—C45—H45	120.0
C26—C21—N1	120.11 (18)	C45—C46—C41	119.4 (2)
C21—C22—C23	119.9 (2)	C45—C46—H46	120.3
C21—C22—H22	120.0	C41—C46—H46	120.3
C23—C22—H22	120.0

Experimental details

Crystal data
Chemical formula	C₂₈H₂₀N₄O₄S
M_r	508.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.9075 (4), 19.0621 (7), 13.5418 (5)
β (°)	108.977 (2)
V (Å³)	2418.47 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.34 × 0.2 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22681, 4264, 3379
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.07
No. of reflections	4264
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.20

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

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3,4-Dinitro-N,N,N',N'-tetra­phenyl­thio­phene-2,5-diamine

Supporting information

Key indicators

checkCIF/PLATON results

3,4-Dinitro-N,N,N',N'-tetraphenylthiophene-2,5-diamine