Bis(2,3-di­chloro­phen­yl) di­sulfide

Osorio-Yáñez, R.N.; Crisóstomo-Lucas, C.; Santacruz-Juárez, E.; Reyes-Martínez, R.; Morales-Morales, D.

doi:10.1107/S1600536814007326

organic compounds

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Volume 70| Part 5| May 2014| Page o529

doi:10.1107/S1600536814007326

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Bis(2,3-dichlorophenyl) disulfide

Rebeca Nayely Osorio-Yáñez,^a Carmela Crisóstomo-Lucas,^a Ericka Santacruz-Juárez,^b ^* Reyna Reyes-Martínez ^a and David Morales-Morales ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, D.F., 04510, Mexico, and ^bUniversidad Politécnica de Tlaxcala, Av. Universidad Politécnica de Tlaxcala No. 1, San Pedro Xalcaltzinco Municipio de Tepeyanco, Tlaxcala, C.P. 90180, Mexico
^*Correspondence e-mail: ericka.santacruz@uptlax.edu.mx

(Received 24 March 2014; accepted 2 April 2014; online 9 April 2014)

The title compound, C₁₂H₆Cl₄S₂, features an S—S bond [2.0252 (8) Å] that bridges two 2,3-dichlorophenyl rings with a C—S—S—C torsion angle of 88.35 (11)°. The benzene rings are normal one to the other with a dihedral angle of 89.83 (11)°. The crystal structure features intermolecular Cl⋯Cl [3.4763 (11) Å] and π–π stacking interactions [centroid–centroid distances = 3.696 (1) and 3.641 (2) Å]. Intramolecular C—H⋯S interactions are also observed.

CCDC reference: 994982

Related literature

For applications of disulfide compounds, see: Crowley (1964 ); Hashash et al. (2002 ); Gomez-Benitez et al. (2006 ); Yu et al. (2010 ). For various methods of synthesizing disulfides, see: Xiao et al. (2009 ); Shaabani et al. (2008 ); Ogilby (2010 ). For similar compounds and their crystal structures, see: Deng et al. (2003 ); Korp & Bernal (1984 ); Tang et al. (2011 ). For disulfide bonds in proteins, see: Sevier & Kaiser (2006 ). For van der Waals radii, see: Bondi (1964 ).

Experimental

Crystal data

C₁₂H₆Cl₄S₂
M_r = 356.09
Triclinic, $[P \overline 1]$
a = 7.7149 (10) Å
b = 7.7326 (11) Å
c = 12.748 (2) Å
α = 91.472 (2)°
β = 91.233 (3)°
γ = 114.859 (2)°
V = 689.37 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 298 K
0.37 × 0.24 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.678, T_max = 0.862
7044 measured reflections
3130 independent reflections
2594 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.088
S = 1.03
3130 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯S2	0.93	2.70	3.202 (2)	115
C12—H12⋯S1	0.93	2.70	3.199 (2)	115

Data collection: APEX2 (Bruker, 2012 ); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; 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, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 994982

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007326/bx2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007326/bx2456Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007326/bx2456Isup3.cml

checkCIF report

Introduction top

The disulfide bonds are found in proteins (Sevier and Kaiser, 2006), natural products and pharmacologically active compounds. Disulfide compounds have shown to exhibit activity as fungicide, mildew-proofing (Crowley, 1964) and antitumor agents (Hashash et al., 2002). In organic synthesis disulfides are used in cross-coupling reactions catalyzed by transition metal compounds such as palladium, nickel and copper (Gomez-Benitez et al., 2006; Yu et al., 2010).

Several methods for the synthesis of disulfides have been reported. These processes involve the oxidative coupling of mercaptans by various oxidants such as molecular oxygen, nitric oxide, solvent-free permanganate, metal ions and promoted by sulfonyl chloride in aqueous media (Xiao et al., 2009; Shaabani et al., 2008; Ogilby, 2010).

Thus, in this report we present the crystal structure of the bis(2,3-dichlorophenyl)disulfide obtained by a nucleophilic substitution reaction. The structure is represented in figure 1.

Experimental top

Synthesis and crystallization top

The title compound was obtained as a by-product of the reaction between 2-(chloromethyl)benzimidazole (0.2 g) and the lead salt of 2,3-dichlorobenzethiol ([Pb(SC₆H₃-2,3-Cl₂)₂]) (0.337 g) in toluene. The resulting reaction mixture was allowed to proceed under reflux by 8 h after which time the formation of PbCl₂ was observed indicating completion of the reaction. The reaction mixture was then filtered through a short Celite plug to afford a colorless solution, the solvent was evaporated under vacuum and the residue column chromatographed (silica gel 60, eluted with 3/2 ethyl acetate/hexane system). Slow Evaporation of the first fraction collected produced crystals of the title compound suitable for X-ray diffraction analysis.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

H atoms were included in calculated positions (C—H = 0.93 A for aromatic H) and refined using a riding model with Uiso(H) = 1.2 Ueq of the carrier atoms.

In the refinement six reflections, (2 0 0), (0 1 3), (0 0 1), (-2 1 2), (2 -4 3) and (-1 0 1), were considered as disagreeable and were omitted.

Results and discussion top

The asymmetric unit of the title compound consists of one molecule on the disulfide. The rings of the bis(2,3-dichlorophenyl)disulfide show a dihedral angle of 89.83° between the two planes and a torsion angle C1—S1—S2—C7 of 88.35 (11)°. The value of the C—S—S—C torsion angle is similar to those found in similar compounds, such as bis(pentachlorophenyl)disulfide (Deng et al., 2003), diphenyldisulfide (Korp & Bernal, 1984) and bis(4-amino-2-chlorophenyl)disulfide (Tang et al., 2011). The S—S distance is 2.0252 (8) Å, whereas the C—S distances are 1.784 (2) and 1.7835 (19) Å. These values are similar and close in value to compounds such as bis(pentachlorophenyl)disulfide with a S—S distance of 2.063 (2) Å and bis(4-amino-2-chlorophenyl)disulfide of 2.0671 (16) Å. The crystal packing is stabilized by π-π and Cl···Cl interactions (Figure 2). The π-π interactions of the 2,3-dichlorophenyl rings presents distances between centroids of 3.696 (1) and 3.641 (2) Å. The Cl1···Cl2 contact distance is of 3.476 Å that is close to the sum of the van der Waals radii of the chloride atoms (Bondi, 1964). The sulphur atoms present C—H···S intramolecular interactions, these values are in the table 1.

Related literature top

For applications of disulfide compounds, see: Crowley (1964); Hashash et al. (2002); Gomez-Benitez et al. (2006); Yu et al. (2010). For synthesis methods for disulfides, see: Xiao et al. (2009); Shaabani et al. (2008); Ogilby (2010). For similar compounds, see: Deng et al. (2003); Korp & Bernal (1984); Tang et al. (2011). For disulfide bonds in proteins, see: Sevier & Kaiser (2006). For van der Waals radii, see: Bondi (1964).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 40% probability of displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. Representation of the π-π and Cl···Cl interactions shown by dashed lines. Hydrogen atoms are omitted.

Bis(2,3-dichlorophenyl) disulfide top

Crystal data top

C₁₂H₆Cl₄S₂	Z = 2
M_r = 356.09	F(000) = 356
Triclinic, P1	D_x = 1.715 Mg m⁻³
a = 7.7149 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7326 (11) Å	Cell parameters from 4288 reflections
c = 12.748 (2) Å	θ = 2.8–27.5°
α = 91.472 (2)°	µ = 1.14 mm⁻¹
β = 91.233 (3)°	T = 298 K
γ = 114.859 (2)°	Prism, colourless
V = 689.37 (18) Å³	0.37 × 0.24 × 0.14 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2594 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.333 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −10→10
T_min = 0.678, T_max = 0.862	l = −16→16
7044 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0397P)² + 0.1749P] where P = (F_o² + 2F_c²)/3
3130 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₂H₆Cl₄S₂	γ = 114.859 (2)°
M_r = 356.09	V = 689.37 (18) Å³
Triclinic, P1	Z = 2
a = 7.7149 (10) Å	Mo Kα radiation
b = 7.7326 (11) Å	µ = 1.14 mm⁻¹
c = 12.748 (2) Å	T = 298 K
α = 91.472 (2)°	0.37 × 0.24 × 0.14 mm
β = 91.233 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3130 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	2594 reflections with I > 2σ(I)
T_min = 0.678, T_max = 0.862	R_int = 0.023
7044 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
3130 reflections	Δρ_min = −0.30 e Å⁻³
163 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
Cl1	0.81619 (10)	0.72799 (9)	0.12199 (5)	0.06495 (19)
Cl2	1.23381 (10)	0.95252 (8)	0.04969 (5)	0.0714 (2)
Cl3	0.64782 (10)	−0.26178 (7)	0.37441 (5)	0.06220 (18)
Cl4	0.75120 (11)	−0.22491 (11)	0.61516 (5)	0.0772 (2)
S1	0.67633 (8)	0.32903 (8)	0.20430 (5)	0.05302 (16)
S2	0.64526 (8)	0.07120 (7)	0.25388 (4)	0.05061 (16)
C1	0.9189 (3)	0.4447 (3)	0.16702 (13)	0.0369 (4)
C2	0.9766 (3)	0.6267 (3)	0.12843 (13)	0.0372 (4)
C3	1.1620 (3)	0.7266 (3)	0.09688 (15)	0.0433 (4)
C4	1.2912 (3)	0.6466 (3)	0.10343 (18)	0.0539 (5)
H4	1.4159	0.7138	0.0825	0.065*
C5	1.2338 (3)	0.4663 (3)	0.14126 (18)	0.0548 (5)
H5	1.3207	0.4119	0.1455	0.066*
C6	1.0495 (3)	0.3650 (3)	0.17301 (16)	0.0462 (5)
H6	1.0129	0.2434	0.1984	0.055*
C7	0.7117 (3)	0.1092 (3)	0.39027 (14)	0.0364 (4)
C8	0.7107 (3)	−0.0468 (3)	0.44284 (14)	0.0378 (4)
C9	0.7575 (3)	−0.0306 (3)	0.54892 (16)	0.0447 (5)
C10	0.8069 (3)	0.1407 (4)	0.60354 (17)	0.0564 (6)
H10	0.8395	0.1517	0.6748	0.068*
C11	0.8078 (3)	0.2947 (3)	0.55208 (18)	0.0561 (6)
H11	0.8405	0.4099	0.5891	0.067*
C12	0.7608 (3)	0.2809 (3)	0.44603 (17)	0.0460 (5)
H12	0.7620	0.3864	0.4121	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0859 (4)	0.0712 (4)	0.0671 (4)	0.0592 (3)	0.0296 (3)	0.0276 (3)
Cl2	0.0806 (4)	0.0444 (3)	0.0751 (4)	0.0115 (3)	0.0078 (3)	0.0195 (3)
Cl3	0.0915 (5)	0.0416 (3)	0.0596 (4)	0.0333 (3)	0.0146 (3)	0.0022 (2)
Cl4	0.0910 (5)	0.0889 (5)	0.0677 (4)	0.0512 (4)	0.0099 (3)	0.0389 (3)
S1	0.0447 (3)	0.0628 (3)	0.0570 (3)	0.0262 (3)	0.0104 (2)	0.0284 (3)
S2	0.0609 (3)	0.0430 (3)	0.0377 (3)	0.0117 (2)	−0.0002 (2)	0.0080 (2)
C1	0.0414 (10)	0.0419 (9)	0.0290 (9)	0.0188 (8)	0.0000 (7)	0.0059 (7)
C2	0.0487 (11)	0.0412 (9)	0.0274 (9)	0.0246 (9)	0.0011 (7)	0.0022 (7)
C3	0.0511 (12)	0.0395 (10)	0.0329 (9)	0.0128 (9)	−0.0014 (8)	0.0030 (7)
C4	0.0364 (11)	0.0659 (14)	0.0526 (13)	0.0148 (10)	−0.0018 (9)	0.0069 (11)
C5	0.0465 (12)	0.0707 (14)	0.0576 (13)	0.0348 (11)	−0.0038 (10)	0.0085 (11)
C6	0.0476 (11)	0.0481 (11)	0.0481 (11)	0.0251 (9)	−0.0026 (9)	0.0112 (9)
C7	0.0341 (9)	0.0373 (9)	0.0347 (9)	0.0116 (7)	0.0058 (7)	0.0057 (7)
C8	0.0383 (10)	0.0372 (9)	0.0396 (10)	0.0168 (8)	0.0093 (8)	0.0062 (7)
C9	0.0377 (10)	0.0543 (12)	0.0433 (11)	0.0197 (9)	0.0065 (8)	0.0144 (9)
C10	0.0462 (12)	0.0723 (15)	0.0395 (11)	0.0141 (11)	−0.0012 (9)	0.0010 (10)
C11	0.0520 (13)	0.0469 (12)	0.0547 (13)	0.0070 (10)	0.0028 (10)	−0.0125 (10)
C12	0.0456 (11)	0.0338 (9)	0.0536 (12)	0.0115 (8)	0.0046 (9)	0.0054 (8)

Geometric parameters (Å, º) top

Cl1—C2	1.7224 (19)	C5—C6	1.380 (3)
Cl2—C3	1.725 (2)	C5—H5	0.9300
Cl3—C8	1.7291 (19)	C6—H6	0.9300
Cl4—C9	1.726 (2)	C7—C12	1.389 (3)
S1—C1	1.784 (2)	C7—C8	1.392 (3)
S1—S2	2.0252 (8)	C8—C9	1.381 (3)
S2—C7	1.7834 (19)	C9—C10	1.378 (3)
C1—C6	1.386 (3)	C10—C11	1.372 (3)
C1—C2	1.393 (2)	C10—H10	0.9300
C2—C3	1.384 (3)	C11—C12	1.382 (3)
C3—C4	1.378 (3)	C11—H11	0.9300
C4—C5	1.378 (3)	C12—H12	0.9300
C4—H4	0.9300

C1—S1—S2	105.09 (7)	C1—C6—H6	120.0
C7—S2—S1	105.02 (7)	C12—C7—C8	119.02 (17)
C6—C1—C2	119.06 (18)	C12—C7—S2	124.42 (15)
C6—C1—S1	124.55 (15)	C8—C7—S2	116.55 (14)
C2—C1—S1	116.38 (14)	C9—C8—C7	120.32 (17)
C3—C2—C1	120.36 (18)	C9—C8—Cl3	120.28 (15)
C3—C2—Cl1	120.22 (14)	C7—C8—Cl3	119.39 (14)
C1—C2—Cl1	119.42 (15)	C10—C9—C8	120.27 (19)
C4—C3—C2	120.23 (18)	C10—C9—Cl4	119.19 (17)
C4—C3—Cl2	119.41 (17)	C8—C9—Cl4	120.53 (16)
C2—C3—Cl2	120.36 (16)	C11—C10—C9	119.6 (2)
C5—C4—C3	119.4 (2)	C11—C10—H10	120.2
C5—C4—H4	120.3	C9—C10—H10	120.2
C3—C4—H4	120.3	C10—C11—C12	120.9 (2)
C4—C5—C6	121.0 (2)	C10—C11—H11	119.5
C4—C5—H5	119.5	C12—C11—H11	119.5
C6—C5—H5	119.5	C11—C12—C7	119.85 (19)
C5—C6—C1	119.93 (19)	C11—C12—H12	120.1
C5—C6—H6	120.0	C7—C12—H12	120.1

S2—S1—C1—C6	0.06 (18)	S1—S2—C7—C12	3.60 (18)
S2—S1—C1—C2	179.34 (12)	S1—S2—C7—C8	−177.28 (13)
C6—C1—C2—C3	−0.2 (3)	C12—C7—C8—C9	0.1 (3)
S1—C1—C2—C3	−179.52 (14)	S2—C7—C8—C9	−179.02 (14)
C6—C1—C2—Cl1	−179.31 (14)	C12—C7—C8—Cl3	179.45 (14)
S1—C1—C2—Cl1	1.4 (2)	S2—C7—C8—Cl3	0.3 (2)
C1—C2—C3—C4	0.0 (3)	C7—C8—C9—C10	−0.5 (3)
Cl1—C2—C3—C4	179.07 (16)	Cl3—C8—C9—C10	−179.76 (16)
C1—C2—C3—Cl2	−179.68 (14)	C7—C8—C9—Cl4	178.52 (14)
Cl1—C2—C3—Cl2	−0.6 (2)	Cl3—C8—C9—Cl4	−0.8 (2)
C2—C3—C4—C5	0.3 (3)	C8—C9—C10—C11	0.6 (3)
Cl2—C3—C4—C5	179.91 (17)	Cl4—C9—C10—C11	−178.44 (17)
C3—C4—C5—C6	−0.3 (3)	C9—C10—C11—C12	−0.3 (3)
C4—C5—C6—C1	0.0 (3)	C10—C11—C12—C7	0.0 (3)
C2—C1—C6—C5	0.2 (3)	C8—C7—C12—C11	0.1 (3)
S1—C1—C6—C5	179.46 (16)	S2—C7—C12—C11	179.18 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S2	0.93	2.70	3.202 (2)	115
C12—H12···S1	0.93	2.70	3.199 (2)	115

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S2	0.93	2.70	3.202 (2)	114.9
C12—H12···S1	0.93	2.70	3.199 (2)	114.8

Acknowledgements

This work was supported by CONACYT (grant No. CB2010–154732) and PAPIIT (grants IN201711–3 and IN213214–3). ESJ thanks PROMEP "Apoyo a perfil deseable". RRM and DMM thank Dr Ruben A. Toscano for technical assistance.

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o529

doi:10.1107/S1600536814007326

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