4,5-Bis­(benzoyl­sulfanyl)-1,3-di­thiol-2-one

Comerlato, N.M.; Ferreira, G.B.; Skakle, J.M.S.; Wardell, J.L.

doi:10.1107/S1600536804028387

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 60| Part 12| December 2004| Pages o2284-o2286

https://doi.org/10.1107/S1600536804028387

4,5-Bis(benzoylsulfanyl)-1,3-dithiol-2-one

Nadia M. Comerlato,^a Gláucio B. Ferreira,^a Janet M. S. Skakle ^b ^* and James L. Wardell ^a

^aDepartamento de Química Inorgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil, and ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: j.skakle@abdn.ac.uk

(Received 2 November 2004; accepted 4 November 2004; online 13 November 2004)

The title compound [systematic name: S,S′-2-oxo-1,3-dithiol-4,5-diyl bis(thiobenzoate)], C₁₇H₁₀O₃S₄, obtained from 4,5-bis(benzoylsulfanyl)-1,3-dithiole-2-thione and mercury(II) acetate in acetic acid/chloroform, exists as isolated molecules with no significant intermolecular S⋯S, S⋯O or O⋯O interactions.

Comment

The title compound, 4,5-bis(benzoylsulfanyl)-1,3-dithiol-2-one, (I), and the zincate salts [Q]₂[Zn(dmio)₂] (Q is the onium cation and dmio is 2-oxo-1,3-dithiole-4,5-dithiolate) are very useful stable sources of the dmio dianion and have found extended use as precursors of both organic dmio compounds and metal–dmio complexes. Additionally, dmio compounds, such as the title compound, are good sources of tetrathiafulvalenes on reaction with phosphites (Svenstrup & Becher, 1995 ).

While the crystal structure of a Zn(dmio)₂ salt has been reported (Candiota et al., 2003 ), no previous study of the structure of (I) has been reported.

Bond lengths and angles within the five-membered dmio ring in (I) are within the ranges found for other dmio compounds, such as [Q][Sn(dmio)₃] and [Q][Zn(dmio)₂] (Candiota et al., 2003; Chohan et al., 2003 ; Aupers et al., 2002 ; de Assis et al., 1999 ).

The dmio ring, together with the attached carbonyl O atom, is essentially planar, with S1 showing the largest deviation [0.0158 (6) Å] from the mean plane. The two phenyl rings are inclined at angles of 78.60 (4) (C11–C16) and 6.94 (8)° (C21–C26) to the dmio ring. Molecules of (I) show no strong association with each other, the closest intermolecular S⋯S, S⋯O and O⋯O separations being 3.6561 (5), 3.4524 (12) and 3.1479 (17) Å, respectively, all just outside the van der Waals radii sum for the appropriate atoms; van der Waals radii for S and O are taken as 1.80 and 1.52 Å, respectively (PLATON; Spek, 2004 ).

The structure of the analogous 4,5-bis(benzoylsulfanyl)-1,3-dithiole-2-thione compound, (II), has been reported at both 120 (Cox & Doidge-Harrison, 1996 ) and 288 K (Solans et al., 1987 ). There are weak C—H⋯O and S⋯S intermolecular interactions in (II).

Figure 1
The molecule of (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as circles of arbitrary radii.

Figure 2
The unit cell contents of (I

), projected on to the (101) plane.

Experimental

The title compound was prepared using a modification of a published method (Hartke et al., 1980 ). A solution of mercury(II) acetate (4.78 g, 15.0 mmol) in glacial acetic acid (120 ml) was added with vigorous agitation to a solution of 4,5-bis(benzoylsulfanyl)-1,3-dithiole-2-thione [(II); 6.09 g, 15.0 mmol] (Steimecke, 1979 ) in chloroform (120 ml). After refluxing for 5 h, the reaction mixture was filtered, and the filtrate was successively washed with water, saturated aqueous sodium bicarbonate solution and more water, dried over MgSO₄ and evaporated to leave a yellow solid, which was recrystallized from chloroform/methanol (yield 54%, m.p. 388–389 K). IR (CsI, cm⁻¹): 3083 (ν C—H), 1701, 1697, 1668, 1621 (ν C=O), 1467 (ν C=C), 896 (ν C—S).

Crystal data

C₁₇H₁₀O₃S₄
M_r = 390.49
Monoclinic, C2/c
a = 35.6460 (6) Å
b = 5.20360 (10) Å
c = 19.1402 (3) Å
β = 116.0945 (8)°
V = 3188.39 (10) Å³
Z = 8
D_x = 1.627 Mg m⁻³
Mo Kα radiation
Cell parameters from 4041 reflections
θ = 2.7–27.5°
μ = 0.61 mm⁻¹
T = 120 (2) K
Block, colourless
0.60 × 0.30 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer with rotating-anode source
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.787, T_max = 0.883
25 707 measured reflections
3656 independent reflections
3191 reflections with I > 2σ(I)
R_int = 0.030
θ_max = 27.5°
h = −46 → 46
k = −6 → 6
l = −24 → 24

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.065
S = 1.06
3656 reflections
217 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.031P)² + 3.4602P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯S3	0.95	2.59	3.0392 (15)	109
C26—H26⋯S4	0.95	2.58	3.0146 (14)	108

All H atoms were first identified in a difference map and then placed in geometrical positions and refined using a riding model with C–H distances of 0.95 Å. Analysis of molecular interactions was carried out using PLATON (Spek, 2004).

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536804028387/lh6308sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536804028387/lh6308Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; 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: SHELXL97.

4,5-Bis(benzoylsulfanyl)-1,3-dithiol-2-one top

Crystal data top

C₁₇H₁₀O₃S₄	F(000) = 1600
M_r = 390.49	D_x = 1.627 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4041 reflections
a = 35.6460 (6) Å	θ = 2.7–27.5°
b = 5.2036 (1) Å	µ = 0.61 mm⁻¹
c = 19.1402 (3) Å	T = 120 K
β = 116.0945 (8)°	Block, colourless
V = 3188.39 (10) Å³	0.60 × 0.30 × 0.20 mm
Z = 8

Data collection top

Bruker-Nonius FR591 rotating anode diffractometer	3656 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3191 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
φ and ω scans	h = −46→46
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −6→6
T_min = 0.787, T_max = 0.883	l = −24→24
25707 measured reflections

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.031P)² + 3.4602P] where P = (F_o² + 2F_c²)/3
3656 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

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.

All H atoms were located from the difference map then refined using a riding model and the appropriate AFIX commands in SHELXL.

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

	x	y	z	U_iso*/U_eq
S1	0.103610 (11)	−0.37285 (7)	0.31289 (2)	0.01562 (9)
S2	0.170596 (10)	0.02062 (6)	0.36723 (2)	0.01379 (9)
C1	0.10785 (4)	−0.1736 (3)	0.38918 (8)	0.0128 (3)
C2	0.13792 (4)	0.0093 (3)	0.41389 (7)	0.0117 (3)
S3	0.072238 (10)	−0.22872 (7)	0.42787 (2)	0.01456 (9)
S4	0.141682 (10)	0.21377 (6)	0.489622 (19)	0.01325 (8)
C5	0.14634 (4)	−0.2398 (3)	0.30231 (8)	0.0144 (3)
O1	0.15830 (3)	−0.3129 (2)	0.25555 (6)	0.0210 (2)
C3	0.03248 (4)	0.0064 (3)	0.37048 (8)	0.0156 (3)
O3	0.03936 (3)	0.1632 (2)	0.33152 (7)	0.0258 (3)
C11	−0.00718 (4)	−0.0137 (3)	0.37810 (8)	0.0148 (3)
C12	−0.03761 (5)	0.1718 (3)	0.34099 (9)	0.0197 (3)
H12	−0.0328	0.3035	0.3115	0.024*
C13	−0.07498 (5)	0.1644 (3)	0.34707 (9)	0.0217 (3)
H13	−0.0957	0.2919	0.3220	0.026*
C14	−0.08222 (4)	−0.0285 (3)	0.38965 (8)	0.0181 (3)
H14	−0.1078	−0.0331	0.3937	0.022*
C15	−0.05214 (5)	−0.2143 (3)	0.42622 (10)	0.0241 (3)
H15	−0.0571	−0.3465	0.4553	0.029*
C16	−0.01465 (5)	−0.2077 (3)	0.42043 (10)	0.0231 (3)
H16	0.0059	−0.3359	0.4454	0.028*
C4	0.18540 (4)	0.4181 (3)	0.50620 (8)	0.0138 (3)
O4	0.20356 (3)	0.4106 (2)	0.46565 (6)	0.0222 (2)
C21	0.19594 (4)	0.6008 (3)	0.57182 (8)	0.0125 (3)
C22	0.22677 (4)	0.7850 (3)	0.58349 (8)	0.0142 (3)
H22	0.2406	0.7867	0.5508	0.017*
C23	0.23726 (4)	0.9649 (3)	0.64249 (8)	0.0157 (3)
H23	0.2583	1.0888	0.6505	0.019*
C24	0.21686 (4)	0.9640 (3)	0.69012 (8)	0.0154 (3)
H24	0.2235	1.0900	0.7297	0.019*
C25	0.18678 (4)	0.7790 (3)	0.67965 (8)	0.0150 (3)
H25	0.1733	0.7769	0.7128	0.018*
C26	0.17627 (4)	0.5969 (3)	0.62096 (8)	0.0144 (3)
H26	0.1558	0.4701	0.6142	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01629 (17)	0.01632 (18)	0.01618 (17)	−0.00254 (13)	0.00890 (14)	−0.00503 (13)
S2	0.01553 (17)	0.01420 (17)	0.01608 (17)	−0.00109 (12)	0.01102 (13)	−0.00182 (12)
C1	0.0123 (6)	0.0145 (6)	0.0136 (6)	0.0017 (5)	0.0074 (5)	−0.0004 (5)
C2	0.0122 (6)	0.0127 (6)	0.0116 (6)	0.0021 (5)	0.0065 (5)	0.0016 (5)
S3	0.01304 (16)	0.01559 (17)	0.01811 (17)	0.00110 (12)	0.00967 (14)	0.00230 (13)
S4	0.01409 (16)	0.01429 (17)	0.01468 (17)	−0.00234 (12)	0.00937 (13)	−0.00326 (12)
C5	0.0162 (6)	0.0135 (7)	0.0145 (7)	0.0023 (5)	0.0075 (6)	0.0011 (5)
O1	0.0259 (6)	0.0229 (5)	0.0204 (5)	0.0003 (4)	0.0159 (5)	−0.0048 (4)
C3	0.0144 (6)	0.0167 (7)	0.0155 (7)	−0.0003 (5)	0.0064 (5)	0.0003 (5)
O3	0.0187 (5)	0.0303 (6)	0.0316 (6)	0.0044 (5)	0.0140 (5)	0.0144 (5)
C11	0.0127 (6)	0.0169 (7)	0.0153 (7)	−0.0014 (5)	0.0066 (5)	−0.0015 (5)
C12	0.0186 (7)	0.0222 (7)	0.0207 (7)	0.0025 (6)	0.0106 (6)	0.0053 (6)
C13	0.0175 (7)	0.0258 (8)	0.0225 (8)	0.0068 (6)	0.0095 (6)	0.0052 (6)
C14	0.0127 (6)	0.0251 (8)	0.0180 (7)	−0.0011 (6)	0.0082 (5)	−0.0023 (6)
C15	0.0200 (7)	0.0257 (8)	0.0309 (9)	0.0013 (6)	0.0151 (7)	0.0088 (7)
C16	0.0164 (7)	0.0220 (8)	0.0331 (9)	0.0049 (6)	0.0130 (7)	0.0099 (7)
C4	0.0141 (6)	0.0132 (6)	0.0151 (6)	−0.0005 (5)	0.0073 (5)	0.0006 (5)
O4	0.0251 (5)	0.0246 (6)	0.0258 (6)	−0.0091 (4)	0.0193 (5)	−0.0088 (5)
C21	0.0128 (6)	0.0119 (6)	0.0128 (6)	0.0020 (5)	0.0056 (5)	0.0010 (5)
C22	0.0127 (6)	0.0157 (7)	0.0154 (7)	0.0011 (5)	0.0072 (5)	0.0014 (5)
C23	0.0124 (6)	0.0159 (7)	0.0168 (7)	−0.0020 (5)	0.0045 (5)	0.0003 (5)
C24	0.0148 (6)	0.0144 (7)	0.0140 (6)	0.0018 (5)	0.0035 (5)	−0.0016 (5)
C25	0.0148 (6)	0.0180 (7)	0.0134 (6)	0.0021 (5)	0.0073 (5)	0.0003 (5)
C26	0.0134 (6)	0.0141 (7)	0.0164 (7)	−0.0011 (5)	0.0073 (5)	0.0005 (5)

Geometric parameters (Å, º) top

S1—C1	1.7424 (14)	C14—C15	1.383 (2)
S1—C5	1.7640 (14)	C14—H14	0.9500
S2—C2	1.7529 (13)	C15—C16	1.389 (2)
S2—C5	1.7839 (14)	C15—H15	0.9500
C1—C2	1.3539 (19)	C16—H16	0.9500
C1—S3	1.7518 (13)	C4—O4	1.2102 (17)
C2—S4	1.7551 (13)	C4—C21	1.4856 (19)
S3—C3	1.8281 (14)	C21—C26	1.3988 (18)
S4—C4	1.7960 (14)	C21—C22	1.4003 (19)
C5—O1	1.2098 (17)	C22—C23	1.386 (2)
C3—O3	1.2013 (18)	C22—H22	0.9500
C3—C11	1.4872 (19)	C23—C24	1.394 (2)
C11—C16	1.391 (2)	C23—H23	0.9500
C11—C12	1.391 (2)	C24—C25	1.389 (2)
C12—C13	1.388 (2)	C24—H24	0.9500
C12—H12	0.9500	C25—C26	1.3891 (19)
C13—C14	1.387 (2)	C25—H25	0.9500
C13—H13	0.9500	C26—H26	0.9500

C1—S1—C5	95.83 (6)	C14—C15—C16	120.08 (14)
C2—S2—C5	95.87 (6)	C14—C15—H15	120.0
C2—C1—S1	118.33 (10)	C16—C15—H15	120.0
C2—C1—S3	125.24 (10)	C15—C16—C11	120.10 (14)
S1—C1—S3	116.43 (8)	C15—C16—H16	120.0
C1—C2—S2	116.56 (10)	C11—C16—H16	120.0
C1—C2—S4	118.41 (10)	O4—C4—C21	123.74 (12)
S2—C2—S4	125.03 (8)	O4—C4—S4	122.32 (11)
C1—S3—C3	98.68 (6)	C21—C4—S4	113.90 (9)
C2—S4—C4	104.47 (6)	C26—C21—C22	119.54 (12)
O1—C5—S1	124.37 (11)	C26—C21—C4	122.96 (12)
O1—C5—S2	122.25 (11)	C22—C21—C4	117.49 (12)
S1—C5—S2	113.37 (7)	C23—C22—C21	120.26 (13)
O3—C3—C11	124.83 (13)	C23—C22—H22	119.9
O3—C3—S3	120.76 (11)	C21—C22—H22	119.9
C11—C3—S3	114.40 (10)	C22—C23—C24	119.96 (13)
C16—C11—C12	119.66 (13)	C22—C23—H23	120.0
C16—C11—C3	122.80 (13)	C24—C23—H23	120.0
C12—C11—C3	117.54 (13)	C25—C24—C23	119.99 (13)
C13—C12—C11	119.97 (14)	C25—C24—H24	120.0
C13—C12—H12	120.0	C23—C24—H24	120.0
C11—C12—H12	120.0	C24—C25—C26	120.41 (13)
C14—C13—C12	120.19 (14)	C24—C25—H25	119.8
C14—C13—H13	119.9	C26—C25—H25	119.8
C12—C13—H13	119.9	C25—C26—C21	119.81 (13)
C15—C14—C13	119.99 (13)	C25—C26—H26	120.1
C15—C14—H14	120.0	C21—C26—H26	120.1
C13—C14—H14	120.0

C5—S1—C1—C2	1.96 (12)	C16—C11—C12—C13	0.7 (2)
C5—S1—C1—S3	−177.98 (8)	C3—C11—C12—C13	−179.09 (14)
S1—C1—C2—S2	−1.50 (15)	C11—C12—C13—C14	−0.4 (2)
S3—C1—C2—S2	178.44 (8)	C12—C13—C14—C15	0.0 (2)
S1—C1—C2—S4	178.93 (7)	C13—C14—C15—C16	0.1 (2)
S3—C1—C2—S4	−1.13 (17)	C14—C15—C16—C11	0.3 (3)
C5—S2—C2—C1	0.19 (12)	C12—C11—C16—C15	−0.7 (2)
C5—S2—C2—S4	179.73 (9)	C3—C11—C16—C15	179.17 (15)
C2—C1—S3—C3	85.59 (13)	C2—S4—C4—O4	5.12 (14)
S1—C1—S3—C3	−94.47 (9)	C2—S4—C4—C21	−176.91 (10)
C1—C2—S4—C4	178.56 (11)	O4—C4—C21—C26	−176.12 (14)
S2—C2—S4—C4	−0.97 (10)	S4—C4—C21—C26	5.94 (17)
C1—S1—C5—O1	178.99 (13)	O4—C4—C21—C22	4.5 (2)
C1—S1—C5—S2	−1.71 (9)	S4—C4—C21—C22	−173.46 (10)
C2—S2—C5—O1	−179.58 (12)	C26—C21—C22—C23	−1.0 (2)
C2—S2—C5—S1	1.11 (9)	C4—C21—C22—C23	178.37 (12)
C1—S3—C3—O3	−10.74 (14)	C21—C22—C23—C24	−0.5 (2)
C1—S3—C3—C11	170.29 (10)	C22—C23—C24—C25	1.6 (2)
O3—C3—C11—C16	176.25 (15)	C23—C24—C25—C26	−1.2 (2)
S3—C3—C11—C16	−4.83 (19)	C24—C25—C26—C21	−0.4 (2)
O3—C3—C11—C12	−3.9 (2)	C22—C21—C26—C25	1.5 (2)
S3—C3—C11—C12	175.00 (11)	C4—C21—C26—C25	−177.93 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···S3	0.95	2.59	3.0392 (15)	109
C26—H26···S4	0.95	2.58	3.0146 (14)	108

Acknowledgements

We thank the EPSRC's X-ray Crystallographic Service, University of Southampton, for the collection of the data. The Brazil-based authors thank CNPq, CAPES and FUJB for support.

References

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