4-Iodo­tetra­thia­fulvalene-1,4-di­nitro­benzene (1/1)

4-Iodo­tetra­thia­fulvalene and 1,4-di­nitro­benzene form a 1:1 molecular complex, C₆H₃IS₄·C₆H₄N₂O₄. The structure comprises mixed stacks of neutral mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.048
• wR factor = 0.119
• Data-to-parameter ratio = 20.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

4-iodotetrathiafulvalene–1,4-dinitrobenzene (1/1)

Crystal data

C6H3IS4·C6H4N2O4	F(000) = 968
Mr = 498.34	Dx = 2.059 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.926 (4) Å	Cell parameters from 763 reflections
b = 7.096 (1) Å	θ = 11.9–23.4°
c = 12.450 (3) Å	µ = 2.53 mm^−1
β = 105.93 (2)°	T = 120 K
V = 1607.8 (6) Å^3	Plate, dark green
Z = 4	0.34 × 0.18 × 0.01 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	4254 independent reflections
Radiation source: fine-focus sealed tube	2903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8 pixels mm^-1	θmax = 29.2°, θmin = 2.2°
ω scans	h = −17→25
Absorption correction: integration (XPREP in SHELXTL; Bruker, 1998), before correction Rint = 0.084	k = −9→9
Tmin = 0.558, Tmax = 0.974	l = −16→16
12107 measured reflections

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0635P)^2] where P = (Fo^2 + 2Fc^2)/3
4254 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 1.61 e Å^−3
0 restraints	Δρmin = −1.96 e Å^−3

Special details

Experimental. The data collection nominally covered over a hemisphere of reciprocal space, by a combination of 4 sets of ω scans; each set at different φ and/or 2θ angles and each scan (30 s exposure) covering 0.3° in ω. Crystal to detector distance 4.54 cm. the absence of crystal decay was confirmed by repeating 50 initial frames at the end of data collection and comparing 267 duplicate reflections.

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.

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

	x	y	z	Uiso*/Ueq
I	0.447878 (18)	0.89038 (5)	0.28996 (3)	0.02045 (11)
S1	0.27408 (7)	0.8999 (2)	0.29177 (10)	0.0183 (3)
S2	0.30376 (7)	0.8349 (2)	0.53584 (10)	0.0191 (3)
S3	0.09485 (7)	0.8846 (2)	0.27354 (11)	0.0276 (3)
S4	0.13378 (8)	0.8179 (2)	0.51763 (11)	0.0242 (3)
C1	0.2376 (3)	0.8664 (7)	0.4064 (4)	0.0173 (10)
C2	0.3650 (3)	0.8721 (7)	0.3707 (4)	0.0157 (10)
C3	0.3789 (3)	0.8425 (8)	0.4815 (4)	0.0201 (11)
H3	0.4275	0.8267	0.5276	0.024*
C4	0.1647 (3)	0.8590 (7)	0.3988 (4)	0.0188 (11)
C5	0.0243 (3)	0.8271 (10)	0.3320 (5)	0.0357 (15)
H5	−0.0249	0.8170	0.2873	0.043*
C6	0.0415 (3)	0.7975 (10)	0.4424 (5)	0.0344 (15)
H6	0.0050	0.7666	0.4784	0.041*
O1	0.4605 (2)	0.3674 (6)	0.4196 (4)	0.0325 (10)
O2	0.3927 (2)	0.4019 (6)	0.2499 (3)	0.0293 (9)
O3	0.1497 (2)	0.2938 (7)	0.5923 (3)	0.0370 (11)
O4	0.0838 (2)	0.3422 (7)	0.4217 (4)	0.0365 (11)
N1	0.4009 (2)	0.3828 (6)	0.3505 (4)	0.0211 (9)
N2	0.1423 (3)	0.3278 (7)	0.4931 (4)	0.0252 (10)
C11	0.3341 (3)	0.3788 (7)	0.3888 (4)	0.0160 (10)
C12	0.3405 (3)	0.3338 (8)	0.5001 (4)	0.0207 (11)
H12	0.3871	0.3130	0.5513	0.025*
C13	0.2769 (3)	0.3206 (8)	0.5333 (4)	0.0229 (11)
H13	0.2793	0.2918	0.6085	0.027*
C14	0.2103 (3)	0.3492 (7)	0.4573 (4)	0.0197 (11)
C15	0.2037 (3)	0.3977 (7)	0.3455 (4)	0.0192 (10)
H15	0.1570	0.4196	0.2948	0.023*
C16	0.2667 (3)	0.4128 (7)	0.3114 (4)	0.0190 (10)
H16	0.2643	0.4456	0.2367	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I	0.01999 (18)	0.02319 (18)	0.02090 (18)	−0.00217 (15)	0.01021 (12)	−0.00096 (15)
S1	0.0170 (6)	0.0251 (6)	0.0133 (6)	0.0005 (5)	0.0047 (4)	0.0015 (5)
S2	0.0189 (6)	0.0248 (7)	0.0133 (6)	−0.0002 (5)	0.0042 (5)	0.0008 (5)
S3	0.0198 (7)	0.0432 (8)	0.0186 (6)	0.0014 (6)	0.0032 (5)	0.0006 (6)
S4	0.0232 (7)	0.0343 (8)	0.0184 (6)	−0.0020 (6)	0.0110 (5)	−0.0011 (6)
C1	0.023 (3)	0.015 (3)	0.014 (2)	0.002 (2)	0.0055 (19)	−0.0025 (19)
C2	0.013 (2)	0.019 (3)	0.016 (2)	0.0002 (19)	0.0048 (18)	−0.002 (2)
C3	0.016 (2)	0.024 (3)	0.020 (3)	−0.001 (2)	0.005 (2)	−0.001 (2)
C4	0.022 (3)	0.020 (3)	0.015 (2)	0.001 (2)	0.007 (2)	0.000 (2)
C5	0.018 (3)	0.054 (4)	0.034 (3)	−0.002 (3)	0.004 (2)	0.000 (3)
C6	0.026 (3)	0.045 (4)	0.038 (4)	−0.005 (3)	0.018 (3)	−0.005 (3)
O1	0.0175 (19)	0.042 (3)	0.036 (2)	0.0049 (18)	0.0045 (17)	−0.006 (2)
O2	0.026 (2)	0.037 (2)	0.029 (2)	0.0031 (18)	0.0140 (17)	0.001 (2)
O3	0.047 (3)	0.047 (3)	0.022 (2)	−0.009 (2)	0.0168 (19)	0.001 (2)
O4	0.028 (2)	0.054 (3)	0.029 (2)	−0.004 (2)	0.0108 (19)	−0.002 (2)
N1	0.024 (2)	0.017 (2)	0.025 (2)	0.0005 (19)	0.0107 (18)	−0.006 (2)
N2	0.024 (2)	0.032 (3)	0.022 (2)	−0.007 (2)	0.0110 (19)	−0.007 (2)
C11	0.015 (2)	0.015 (2)	0.018 (2)	0.001 (2)	0.0041 (19)	−0.004 (2)
C12	0.019 (3)	0.023 (3)	0.017 (2)	0.001 (2)	−0.001 (2)	−0.002 (2)
C13	0.029 (3)	0.025 (3)	0.015 (2)	0.001 (2)	0.007 (2)	0.000 (2)
C14	0.027 (3)	0.017 (3)	0.019 (2)	−0.006 (2)	0.011 (2)	−0.001 (2)
C15	0.020 (3)	0.021 (2)	0.016 (2)	−0.002 (2)	0.0042 (19)	0.001 (2)
C16	0.021 (3)	0.017 (3)	0.019 (2)	0.002 (2)	0.006 (2)	0.001 (2)

Geometric parameters (Å, º)

I—C2	2.085 (5)	O2—N1	1.227 (6)
S1—C2	1.743 (5)	O3—N2	1.229 (6)
S1—C1	1.765 (5)	O4—N2	1.219 (6)
S2—C3	1.736 (5)	N1—C11	1.469 (7)
S2—C1	1.763 (5)	N2—C14	1.481 (7)
S3—C5	1.736 (6)	C11—C16	1.393 (7)
S3—C4	1.755 (5)	C11—C12	1.394 (7)
S4—C6	1.746 (6)	C12—C13	1.379 (8)
S4—C4	1.759 (5)	C12—H12	0.9476
C1—C4	1.357 (7)	C13—C14	1.368 (8)
C2—C3	1.348 (7)	C13—H13	0.9479
C3—H3	0.9476	C14—C15	1.406 (7)
C5—C6	1.338 (9)	C15—C16	1.374 (7)
C5—H5	0.9476	C15—H15	0.9476
C6—H6	0.9480	C16—H16	0.9479
O1—N1	1.221 (6)
C2—S1—C1	94.3 (2)	O1—N1—C11	118.8 (5)
C3—S2—C1	95.3 (3)	O2—N1—C11	117.0 (4)
C5—S3—C4	94.7 (3)	O4—N2—O3	125.4 (5)
C6—S4—C4	94.4 (3)	O4—N2—C14	117.6 (5)
C4—C1—S2	120.9 (4)	O3—N2—C14	117.0 (5)
C4—C1—S1	124.4 (4)	C16—C11—C12	122.7 (5)
S2—C1—S1	114.7 (3)	C16—C11—N1	118.6 (5)
C3—C2—S1	118.6 (4)	C12—C11—N1	118.6 (4)
C3—C2—I	122.8 (4)	C13—C12—C11	117.9 (5)
S1—C2—I	118.6 (3)	C13—C12—H12	121.1
C2—C3—S2	117.0 (4)	C11—C12—H12	121.1
C2—C3—H3	121.5	C14—C13—C12	119.8 (5)
S2—C3—H3	121.5	C14—C13—H13	120.0
C1—C4—S3	124.2 (4)	C12—C13—H13	120.1
C1—C4—S4	120.9 (4)	C13—C14—C15	122.4 (5)
S3—C4—S4	114.9 (3)	C13—C14—N2	119.3 (5)
C6—C5—S3	117.9 (5)	C15—C14—N2	118.3 (5)
C6—C5—H5	121.0	C16—C15—C14	118.4 (5)
S3—C5—H5	121.1	C16—C15—H15	120.8
C5—C6—S4	117.7 (5)	C14—C15—H15	120.8
C5—C6—H6	121.2	C15—C16—C11	118.7 (5)
S4—C6—H6	121.2	C15—C16—H16	120.7
O1—N1—O2	124.3 (5)	C11—C16—H16	120.6