4,4′-[Thio­phene-2,5-diylbis(ethyne-2,1-di­yl)]dibenzonitrile

Figueira, J.; Vertlib, V.; Rodrigues, J.; Nättinen, K.; Rissanen, K.

doi:10.1107/S1600536808008106

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages o765-o766

doi:10.1107/S1600536808008106

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4,4′-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile

João Figueira,^a Viatslav Vertlib,^a João Rodrigues,^a Kalle Nättinen ^b and Kari Rissanen ^c ^*

^aCentro de Química da Madeira, LQCMM/MMRG, Departamento de Química da Universidade da Madeira, 9000-390 Funchal, Portugal, ^bVTT, Sinitaival 6, PO Box 1300, FI-33101 Tampere, Finland, and ^cNanoscience Center, Department of Chemistry, University of Jyväskylä, PO Box 35, 40014 Jyväskylä, Finland
^*Correspondence e-mail: Kari.Rissanen@jyu.fi

(Received 5 March 2008; accepted 25 March 2008; online 29 March 2008)

In the solid state, the title compound, C₂₂H₁₀N₂S, forms centrosymmetric dimers by pairs of non-classical C—H⋯S hydrogen bonds linking approximately coplanar molecules. The benzene ring involved in this interaction makes a dihedral angle of only 7.21 (16)° with the thiophene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an interplanar spacing of 3.44 Å. C—H⋯N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each molecule thus interacts with 12 adjacent molecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the molecule.

Related literature

For related literature, see: Rodríguez et al. (2004 , 2006 ); Lind et al. (2004 ); Garcia et al. (2001 ); Ornelas et al. (2005 , 2008 ); Tour (2003 ).

Experimental

Crystal data

C₂₂H₁₀N₂S
M_r = 334.38
Monoclinic, P 2₁ /n
a = 5.4557 (11) Å
b = 19.467 (4) Å
c = 15.592 (3) Å
β = 91.89 (3)°
V = 1655.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 (2) K
0.3 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
19547 measured reflections
2906 independent reflections
1762 reflections with I > 2σ(I)
R_int = 0.102

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.107
S = 1.01
2906 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N1ⁱ	0.95	2.65	3.246 (4)	121
C7—H7⋯N25ⁱⁱ	0.95	2.65	3.384 (4)	134
C20—H20⋯N25ⁱⁱⁱ	0.95	2.55	3.453 (3)	159
C5—H5⋯S12^iv	0.95	3.05	3.832 (3)	141
Symmetry codes: (i) $[-x-{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{5\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+3, -y+1, -z+2; (iv) -x, -y+2, -z+2.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008106/cf2187sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008106/cf2187Isup2.hkl

checkCIF report

Comment top

The preparation of highly conjugated molecules has been of great interest for their potential applications in fields such as nanoelectronics (Tour, 2003) or optoelectronics (Ornelas et al., 2005, 2008; Lind et al., 2004). Terminal cyano groups provide the ability to coordinate to transition metal centres such as RuCp (Cp = cyclopentadienyl; Garcia et al., 2001; Ornelas et al., 2005) which should result in an increase of the physical properties such as the first molecular hyperpolarizability β, which is reported to rise with the coordination to cyclopentadienylruthenium type centres (Ornelas et al., 2005, 2008). As such the preparation of the π-conjugated title compound was intended for the preparation of dinuclear ruthenium complexes for nanoelectronic application.

In the solid state the title compound, C₂₂H₁₀N₂S, forms centrosymmetric dimers by pairs of non-classical C—H···S hydrogen bonds linking approximately coplanar molecules. The benzene ring involved in this interaction makes a dihedral angle of only 7.21 (16)° with the thiophene ring, while the other benzene ring is twisted somewhat out of plane with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an interplanar spacing of 3.44 Å. C—H···N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each molecule thus interacts with twelve ajacent molecules, five of them approaching closer than the sum of van der Waals radii for the relevant atoms. Optimisation of the inter-stack contacts contributes to the non-planarity of the molecule.

Related literature top

For related literature, see: Rodríguez et al. (2004, 2006); Lind et al. (2004); Garcia et al. (2001); Ornelas et al. (2005, 2008); Tour (2003).

Experimental top

The title compound was prepared by Sonogashira cross-coupling (Rodríguez et al., 2004, 2006) of 4-ethynylbenzonitrile (0.901 g, 7.09 mmol) and 2,5-dibromothiophene (0.800 g, 3.30 mmol) in dry tetrahydrofuran (16 ml) and N-ethyldiisopropylamine (25 ml). The reaction was catalysed by PdCl₂(PPh₃)₂ (0.250 g, 0.360 mmol) and CuI (0.068 g, 0.36 mmol). The mixture was left under N₂ atmosphere at room temperature for 17 h and then heated for 2. 5 h at 333–343 K. The resulting reaction mixture was washed with aqueous NH₄Cl and extracted (3 times) with CH₂Cl₂. The resulting solution was dried over Na₂SO₄ and evaporated to dryness. The resulting dark solid was column chromatographed (Silica S60, petroleum ether/CH₂Cl₂ 2:2.5), yielding a pale yellow solid. Slow evaporation of a CH₂Cl₂ solution of the title compound resulted in yellow crystals in 41% yield. ¹H NMR (500 MHz, CD₂Cl₂): δ 7.28 (2H, s, Ar); 7.62 (4H, d, Ar, J_HH = 9 Hz); 7.67 (4H, d, Ar, J_HH = 9 Hz); ¹³C NMR (126 MHz, CD₂Cl₂): δ 86.5, 93.4, 112.7, 118.9, 125.2, 127.8, 132.4, 132.8, 133.6, 133.7; IR (KBr): 2227 (m), 2207 (m), 1663 (w), 1600 (s), 1490 (w),1385 (s), 1110 (w), 865 (s), 839 (s), 802 (m), 555 (m), 536 (w) cm^-1; Mp: decomposes above 393 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids.
	Fig. 2. The packing of (I), viewed along the b axis.
	Fig. 3. An alternate view of the packing of (I), showing the close C—H···N contacts (less that 0.1 Å + sum of vDW radii).

4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile top

Crystal data top

C₂₂H₁₀N₂S	F(000) = 688
M_r = 334.38	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5465 reflections
a = 5.4557 (11) Å	θ = 1.0–25.0°
b = 19.467 (4) Å	µ = 0.20 mm⁻¹
c = 15.592 (3) Å	T = 173 K
β = 91.89 (3)°	Block, colourless
V = 1655.1 (6) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.103
ω and ϕ scans	θ_max = 25.0°, θ_min = 3.4°
19547 measured reflections	h = −6→6
2906 independent reflections	k = −23→23
1762 reflections with I > 2σ(I)	l = −18→18

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0448P)² + 0.1608P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.107	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 0.18 e Å⁻³
2906 reflections	Δρ_min = −0.23 e Å⁻³
226 parameters

Crystal data top

C₂₂H₁₀N₂S	V = 1655.1 (6) Å³
M_r = 334.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.4557 (11) Å	µ = 0.20 mm⁻¹
b = 19.467 (4) Å	T = 173 K
c = 15.592 (3) Å	0.3 × 0.2 × 0.2 mm
β = 91.89 (3)°

Data collection top

Nonius KappaCCD diffractometer	1762 reflections with I > 2σ(I)
19547 measured reflections	R_int = 0.103
2906 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
2906 reflections	Δρ_min = −0.23 e Å⁻³
226 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	−1.0858 (5)	1.19052 (14)	0.88637 (18)	0.0381 (7)
C3	−0.9079 (4)	1.13708 (12)	0.87250 (18)	0.0321 (7)
C4	−0.7199 (4)	1.12636 (12)	0.93351 (18)	0.0350 (7)
H4	−0.7062	1.1548	0.9829	0.042*
C5	−0.5532 (4)	1.07398 (13)	0.92173 (17)	0.0338 (7)
H5	−0.426	1.066	0.9636	0.041*
C6	−0.5711 (4)	1.03261 (12)	0.84841 (17)	0.0300 (6)
C7	−0.7592 (4)	1.04450 (12)	0.78771 (17)	0.0341 (7)
H7	−0.7716	1.0167	0.7376	0.041*
C8	−0.9275 (4)	1.09612 (13)	0.79951 (18)	0.0371 (7)
H8	−1.0561	1.1037	0.758	0.044*
C9	−0.3976 (4)	0.97811 (13)	0.83651 (16)	0.0328 (7)
C10	−0.2514 (4)	0.93344 (12)	0.82613 (17)	0.0318 (6)
C11	−0.0771 (4)	0.88054 (12)	0.81401 (17)	0.0302 (6)
C13	0.2619 (4)	0.79650 (12)	0.83234 (17)	0.0313 (6)
C14	0.1422 (4)	0.79222 (13)	0.75409 (17)	0.0395 (7)
H14	0.1851	0.7604	0.711	0.047*
C15	−0.0503 (5)	0.83959 (13)	0.74389 (18)	0.0388 (7)
H15	−0.1517	0.8428	0.6933	0.047*
C16	0.4557 (5)	0.75490 (13)	0.86692 (17)	0.0342 (7)
C17	0.6095 (4)	0.71891 (13)	0.89930 (17)	0.0329 (7)
C18	0.7787 (4)	0.67373 (12)	0.94359 (17)	0.0303 (6)
C19	0.9777 (4)	0.64472 (12)	0.90311 (17)	0.0332 (7)
H19	1.0049	0.6553	0.8447	0.04*
C20	1.1351 (4)	0.60097 (13)	0.94690 (17)	0.0339 (7)
H20	1.2717	0.5819	0.919	0.041*
C21	1.0941 (4)	0.58472 (12)	1.03170 (18)	0.0298 (6)
C22	0.8960 (4)	0.61295 (13)	1.07333 (18)	0.0346 (7)
H22	0.8682	0.6016	1.1315	0.041*
C23	0.7403 (4)	0.65760 (12)	1.02936 (18)	0.0352 (7)
H23	0.606	0.6775	1.0577	0.042*
C24	1.2582 (5)	0.53837 (13)	1.07783 (17)	0.0330 (7)
N1	−1.2285 (4)	1.23260 (12)	0.89832 (16)	0.0495 (7)
N25	1.3868 (4)	0.50197 (11)	1.11512 (15)	0.0434 (6)
S12	0.13508 (11)	0.85961 (3)	0.89414 (5)	0.0369 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0375 (16)	0.0321 (17)	0.045 (2)	−0.0017 (13)	0.0037 (14)	0.0089 (14)
C3	0.0283 (14)	0.0245 (14)	0.0436 (19)	0.0030 (12)	0.0046 (13)	0.0035 (14)
C4	0.0353 (15)	0.0327 (16)	0.0373 (18)	0.0024 (12)	0.0045 (13)	−0.0046 (13)
C5	0.0295 (14)	0.0381 (16)	0.0332 (18)	−0.0002 (12)	−0.0059 (13)	−0.0021 (14)
C6	0.0286 (14)	0.0263 (15)	0.0352 (18)	−0.0019 (12)	0.0043 (12)	0.0030 (13)
C7	0.0371 (15)	0.0335 (16)	0.0315 (18)	0.0001 (13)	−0.0008 (13)	−0.0010 (13)
C8	0.0328 (15)	0.0383 (17)	0.040 (2)	0.0002 (13)	−0.0031 (13)	0.0054 (15)
C9	0.0314 (15)	0.0358 (16)	0.0313 (18)	−0.0013 (13)	0.0019 (12)	0.0007 (13)
C10	0.0332 (15)	0.0312 (16)	0.0310 (17)	−0.0008 (13)	0.0029 (12)	−0.0005 (13)
C11	0.0296 (14)	0.0265 (14)	0.0347 (18)	0.0017 (11)	0.0027 (12)	0.0045 (13)
C13	0.0303 (14)	0.0275 (15)	0.0363 (18)	0.0030 (12)	0.0043 (12)	0.0054 (13)
C14	0.0504 (17)	0.0369 (17)	0.0312 (19)	0.0158 (14)	0.0024 (14)	0.0009 (14)
C15	0.0492 (17)	0.0386 (17)	0.0285 (18)	0.0105 (14)	−0.0014 (13)	0.0016 (14)
C16	0.0343 (15)	0.0315 (16)	0.0369 (18)	−0.0015 (13)	0.0047 (13)	−0.0001 (14)
C17	0.0315 (15)	0.0305 (15)	0.0367 (18)	−0.0017 (13)	0.0018 (13)	−0.0007 (13)
C18	0.0304 (15)	0.0245 (14)	0.0360 (18)	−0.0026 (12)	−0.0010 (13)	−0.0010 (13)
C19	0.0339 (15)	0.0325 (16)	0.0333 (17)	−0.0018 (13)	0.0036 (13)	0.0032 (13)
C20	0.0301 (15)	0.0325 (16)	0.039 (2)	0.0028 (12)	0.0033 (13)	−0.0019 (14)
C21	0.0272 (14)	0.0254 (15)	0.0366 (19)	−0.0016 (11)	−0.0047 (12)	0.0008 (13)
C22	0.0340 (15)	0.0388 (16)	0.0308 (17)	0.0011 (13)	−0.0001 (13)	−0.0001 (13)
C23	0.0291 (14)	0.0361 (17)	0.0405 (19)	0.0032 (12)	0.0014 (13)	−0.0037 (14)
C24	0.0324 (15)	0.0314 (16)	0.0350 (18)	0.0016 (13)	−0.0026 (13)	−0.0064 (14)
N1	0.0471 (15)	0.0394 (15)	0.0626 (19)	0.0092 (12)	0.0082 (13)	0.0070 (13)
N25	0.0435 (14)	0.0459 (15)	0.0405 (16)	0.0087 (12)	−0.0057 (12)	−0.0037 (12)
S12	0.0353 (4)	0.0392 (4)	0.0360 (5)	0.0052 (3)	−0.0028 (3)	−0.0052 (3)

Geometric parameters (Å, º) top

C2—N1	1.149 (3)	C13—S12	1.721 (3)
C2—C3	1.444 (4)	C14—C15	1.403 (3)
C3—C8	1.391 (4)	C14—H14	0.95
C3—C4	1.392 (4)	C15—H15	0.95
C4—C5	1.383 (3)	C16—C17	1.192 (3)
C4—H4	0.95	C17—C18	1.436 (3)
C5—C6	1.399 (3)	C18—C19	1.393 (3)
C5—H5	0.95	C18—C23	1.396 (3)
C6—C7	1.392 (3)	C19—C20	1.375 (3)
C6—C9	1.438 (3)	C19—H19	0.95
C7—C8	1.378 (3)	C20—C21	1.385 (3)
C7—H7	0.95	C20—H20	0.95
C8—H8	0.95	C21—C22	1.392 (3)
C9—C10	1.195 (3)	C21—C24	1.446 (4)
C10—C11	1.418 (3)	C22—C23	1.382 (3)
C11—C15	1.365 (3)	C22—H22	0.95
C11—S12	1.724 (3)	C23—H23	0.95
C13—C14	1.367 (3)	C24—N25	1.143 (3)
C13—C16	1.424 (4)

N1—C2—C3	179.1 (3)	C13—C14—H14	123.4
C8—C3—C4	120.6 (2)	C15—C14—H14	123.4
C8—C3—C2	120.1 (2)	C11—C15—C14	113.1 (2)
C4—C3—C2	119.3 (2)	C11—C15—H15	123.4
C5—C4—C3	119.5 (2)	C14—C15—H15	123.4
C5—C4—H4	120.2	C17—C16—C13	176.4 (3)
C3—C4—H4	120.2	C16—C17—C18	174.9 (3)
C4—C5—C6	120.3 (2)	C19—C18—C23	119.1 (2)
C4—C5—H5	119.8	C19—C18—C17	121.9 (2)
C6—C5—H5	119.8	C23—C18—C17	118.9 (2)
C7—C6—C5	119.3 (2)	C20—C19—C18	120.6 (2)
C7—C6—C9	120.6 (2)	C20—C19—H19	119.7
C5—C6—C9	120.1 (2)	C18—C19—H19	119.7
C8—C7—C6	120.7 (2)	C19—C20—C21	119.8 (2)
C8—C7—H7	119.7	C19—C20—H20	120.1
C6—C7—H7	119.7	C21—C20—H20	120.1
C7—C8—C3	119.6 (2)	C20—C21—C22	120.5 (2)
C7—C8—H8	120.2	C20—C21—C24	120.1 (2)
C3—C8—H8	120.2	C22—C21—C24	119.5 (2)
C10—C9—C6	179.1 (3)	C23—C22—C21	119.4 (3)
C9—C10—C11	179.8 (3)	C23—C22—H22	120.3
C15—C11—C10	128.4 (2)	C21—C22—H22	120.3
C15—C11—S12	110.82 (18)	C22—C23—C18	120.5 (2)
C10—C11—S12	120.8 (2)	C22—C23—H23	119.8
C14—C13—C16	129.1 (2)	C18—C23—H23	119.8
C14—C13—S12	110.75 (18)	N25—C24—C21	179.2 (3)
C16—C13—S12	120.1 (2)	C13—S12—C11	92.05 (12)
C13—C14—C15	113.3 (2)

C8—C3—C4—C5	−0.8 (4)	C23—C18—C19—C20	−0.2 (4)
C2—C3—C4—C5	178.2 (2)	C17—C18—C19—C20	−179.2 (2)
C3—C4—C5—C6	0.9 (4)	C18—C19—C20—C21	0.9 (4)
C4—C5—C6—C7	−0.4 (4)	C19—C20—C21—C22	−0.7 (4)
C4—C5—C6—C9	−179.9 (2)	C19—C20—C21—C24	179.6 (2)
C5—C6—C7—C8	−0.4 (4)	C20—C21—C22—C23	−0.2 (4)
C9—C6—C7—C8	179.2 (2)	C24—C21—C22—C23	179.6 (2)
C6—C7—C8—C3	0.5 (4)	C21—C22—C23—C18	0.8 (4)
C4—C3—C8—C7	0.0 (4)	C19—C18—C23—C22	−0.6 (4)
C2—C3—C8—C7	−178.9 (2)	C17—C18—C23—C22	178.4 (2)
C16—C13—C14—C15	176.4 (2)	C14—C13—S12—C11	−0.5 (2)
S12—C13—C14—C15	0.1 (3)	C16—C13—S12—C11	−177.2 (2)
C10—C11—C15—C14	−179.9 (2)	C15—C11—S12—C13	0.8 (2)
S12—C11—C15—C14	−0.8 (3)	C10—C11—S12—C13	179.9 (2)
C13—C14—C15—C11	0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1ⁱ	0.95	2.65	3.246 (4)	121
C7—H7···N25ⁱⁱ	0.95	2.65	3.384 (4)	134
C20—H20···N25ⁱⁱⁱ	0.95	2.55	3.453 (3)	159
C5—H5···S12^iv	0.95	3.05	3.832 (3)	141

Symmetry codes: (i) −x−3/2, y−1/2, −z+3/2; (ii) x−5/2, −y+3/2, z−1/2; (iii) −x+3, −y+1, −z+2; (iv) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₀N₂S
M_r	334.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	5.4557 (11), 19.467 (4), 15.592 (3)
β (°)	91.89 (3)
V (Å³)	1655.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19547, 2906, 1762
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.107, 1.01
No. of reflections	2906
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.23

Computer programs: COLLECT (Hooft, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1ⁱ	0.95	2.65	3.246 (4)	121.4
C7—H7···N25ⁱⁱ	0.95	2.65	3.384 (4)	134.4
C20—H20···N25ⁱⁱⁱ	0.95	2.55	3.453 (3)	159.4
C5—H5···S12^iv	0.95	3.05	3.832 (3)	140.7

Symmetry codes: (i) −x−3/2, y−1/2, −z+3/2; (ii) x−5/2, −y+3/2, z−1/2; (iii) −x+3, −y+1, −z+2; (iv) −x, −y+2, −z+2.

Acknowledgements

This research was supported by Fundação para a Ciência e a Tecnologia (Portugal) through FEDER-funded project POCTI/CTM/41495/2001 (JF and JR), the PhD grant SFRH/BD/29325/2006 (JF) and by the sabbatical research grant SFRH/BSAB/632/2006 (JR). JR and JF thank the University of Jyväskylä for supporting their visits, respectively, as a visiting professor and as a PhD student at the Nanoscience Center, Department of Chemistry. The Academy of Finland is gratefully acknowledged for a research grant (No. 122350, KR).

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Volume 64| Part 4| April 2008| Pages o765-o766

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