The title compound, C
16H
10Cl
2S
4, contains a tetrathiane ring that displays a twist conformation. The S—S bond lengths are 2.049 (2) and 2.046 (2) Å. At the methylene C atoms, the C—C—C angles are by far the largest, with values of 127.7 (3) and 126.8 (4)°. The packing involves C—H
S, C—H
Cl and Cl
Cl interactions.
Supporting information
CCDC reference: 185797
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.140
- Data-to-parameter ratio = 14.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
DIFF_012 Alert A _diffrn_reflns_av_R_equivalents is missing
R factor for symmetry-equivalent intensities.
The following tests will not be performed
RINTA
Alert Level C:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 25.05
From the CIF: _reflns_number_total 2845
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3017
Completeness (_total/calc) 94.30%
Alert C: < 95% complete
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Preparation of (3): 870 mg (5.7 mmol) (2) were dissolved in 25 ml dry CS2 and
cooled to liquid-nitrogen temperature. The solution was degassed three times
by allowing it to warm slightly in vacuo. Despite the low temperature,
the solution became slightly yellow. It was then irradiated with UV light (λ
= 380±20 nm) for 4 h at 238 K in a 25 ml quarz cuvette fitted with a cooling
mantle. The resulting red solution was subjected to column chromatography on
silica with hexane as eluent, yielding 180 mg (15%) of a yellow oil (m.p.
414–415 K). Spectroscopic details are given by Wierlacher (1993). Analysis:
calculated C 47.87, H 2.51, S 31.95%; found C 47.97, H 2.51, S 31.68%. Single
crystals were obtained from saturated solutions in hexane.
H atoms were placed in idealized positions and refined using a riding model.
Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
trans-3,6-Bis(chlorophenylmethylene)-1,2,4,5-tetrathiane
top
Crystal data top
C16H10Cl2S4 | Dx = 1.563 Mg m−3 |
Mr = 401.38 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 48 reflections |
a = 7.611 (4) Å | θ = 10–11.2° |
b = 17.137 (5) Å | µ = 0.86 mm−1 |
c = 26.161 (10) Å | T = 133 K |
V = 3412 (2) Å3 | Prism, yellow |
Z = 8 | 0.6 × 0.4 × 0.4 mm |
F(000) = 1632 | |
Data collection top
Stoe STADI-4 diffractometer | θmax = 25.1°, θmin = 3.0° |
Radiation source: fine-focus sealed tube | h = −9→0 |
Graphite monochromator | k = 0→20 |
ω/θ scans | l = 0→31 |
2845 measured reflections | 3 standard reflections every 60 min |
2845 independent reflections | intensity decay: none |
2414 reflections with I > 2σ(I) | |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0776P)2 + 7.2011P] where P = (Fo2 + 2Fc2)/3 |
2845 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
Crystal data top
C16H10Cl2S4 | V = 3412 (2) Å3 |
Mr = 401.38 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 7.611 (4) Å | µ = 0.86 mm−1 |
b = 17.137 (5) Å | T = 133 K |
c = 26.161 (10) Å | 0.6 × 0.4 × 0.4 mm |
Data collection top
Stoe STADI-4 diffractometer | 2414 reflections with I > 2σ(I) |
2845 measured reflections | 3 standard reflections every 60 min |
2845 independent reflections | intensity decay: none |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.38 e Å−3 |
2845 reflections | Δρmin = −0.46 e Å−3 |
199 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. Non-bonded contact: 3.4755 (0.0023) Cl2 - Cl2_$1 132.01 (0.14) C4 - Cl2 - Cl2_$1 Operator: $1 2 -
x,1 - y,1 - z |
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 | Uiso*/Ueq | |
S1 | 0.60339 (13) | 0.48438 (5) | 0.34817 (3) | 0.0284 (3) | |
S2 | 0.46901 (14) | 0.64959 (5) | 0.34243 (4) | 0.0326 (3) | |
S3 | 0.76821 (12) | 0.54307 (5) | 0.39669 (3) | 0.0282 (2) | |
S4 | 0.40854 (13) | 0.61150 (6) | 0.41441 (4) | 0.0326 (3) | |
Cl1 | 0.42775 (15) | 0.64014 (5) | 0.22748 (4) | 0.0372 (3) | |
Cl2 | 0.87739 (14) | 0.58501 (7) | 0.50623 (4) | 0.0441 (3) | |
C1 | 0.5216 (5) | 0.5618 (2) | 0.31008 (13) | 0.0242 (7) | |
C2 | 0.6188 (5) | 0.5893 (2) | 0.43936 (13) | 0.0252 (8) | |
C3 | 0.5001 (5) | 0.5560 (2) | 0.25935 (13) | 0.0266 (8) | |
C4 | 0.6657 (5) | 0.6094 (2) | 0.48640 (13) | 0.0266 (8) | |
C5 | 0.5323 (5) | 0.4880 (2) | 0.22703 (13) | 0.0257 (7) | |
C6 | 0.4831 (5) | 0.4139 (2) | 0.24334 (14) | 0.0313 (8) | |
H6 | 0.4261 | 0.4075 | 0.2754 | 0.038* | |
C7 | 0.5170 (6) | 0.3491 (2) | 0.21298 (15) | 0.0388 (10) | |
H7 | 0.4846 | 0.2986 | 0.2245 | 0.047* | |
C8 | 0.5980 (6) | 0.3581 (2) | 0.16587 (16) | 0.0396 (10) | |
H8 | 0.6221 | 0.3137 | 0.1453 | 0.047* | |
C9 | 0.6434 (5) | 0.4315 (2) | 0.14901 (14) | 0.0348 (9) | |
H9 | 0.6982 | 0.4376 | 0.1166 | 0.042* | |
C10 | 0.6099 (5) | 0.4963 (2) | 0.17885 (14) | 0.0293 (8) | |
H10 | 0.6397 | 0.5468 | 0.1666 | 0.035* | |
C11 | 0.5577 (5) | 0.6518 (2) | 0.52431 (13) | 0.0267 (8) | |
C12 | 0.3871 (5) | 0.6285 (2) | 0.53414 (14) | 0.0317 (8) | |
H12 | 0.3391 | 0.5849 | 0.5166 | 0.038* | |
C13 | 0.2855 (5) | 0.6687 (2) | 0.56963 (15) | 0.0363 (9) | |
H13 | 0.1679 | 0.6528 | 0.5759 | 0.044* | |
C14 | 0.3545 (6) | 0.7315 (2) | 0.59585 (15) | 0.0381 (9) | |
H14 | 0.2853 | 0.7585 | 0.6203 | 0.046* | |
C15 | 0.5254 (6) | 0.7547 (3) | 0.58616 (17) | 0.0428 (10) | |
H15 | 0.5728 | 0.7983 | 0.6039 | 0.051* | |
C16 | 0.6270 (5) | 0.7157 (2) | 0.55136 (15) | 0.0359 (9) | |
H16 | 0.7447 | 0.7318 | 0.5455 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0381 (6) | 0.0253 (5) | 0.0217 (5) | 0.0023 (4) | −0.0019 (4) | −0.0021 (3) |
S2 | 0.0431 (6) | 0.0259 (5) | 0.0287 (5) | 0.0053 (4) | −0.0080 (4) | −0.0049 (4) |
S3 | 0.0273 (5) | 0.0352 (5) | 0.0220 (5) | 0.0040 (4) | 0.0010 (4) | −0.0046 (3) |
S4 | 0.0274 (5) | 0.0438 (6) | 0.0265 (5) | 0.0066 (4) | −0.0025 (4) | −0.0090 (4) |
Cl1 | 0.0499 (6) | 0.0297 (5) | 0.0322 (5) | 0.0019 (4) | −0.0116 (4) | 0.0021 (4) |
Cl2 | 0.0345 (5) | 0.0687 (7) | 0.0290 (5) | 0.0164 (5) | −0.0078 (4) | −0.0083 (5) |
C1 | 0.0245 (18) | 0.0258 (17) | 0.0223 (17) | −0.0011 (14) | −0.0016 (14) | −0.0029 (13) |
C2 | 0.0282 (19) | 0.0275 (17) | 0.0198 (17) | 0.0028 (14) | 0.0011 (14) | −0.0019 (14) |
C3 | 0.0297 (18) | 0.0261 (17) | 0.0240 (18) | −0.0022 (15) | −0.0031 (15) | 0.0047 (14) |
C4 | 0.0285 (19) | 0.0317 (18) | 0.0195 (17) | 0.0002 (15) | −0.0019 (15) | 0.0014 (14) |
C5 | 0.0281 (19) | 0.0285 (18) | 0.0205 (17) | 0.0000 (15) | −0.0057 (14) | −0.0031 (14) |
C6 | 0.038 (2) | 0.0345 (19) | 0.0214 (17) | −0.0046 (16) | −0.0010 (16) | 0.0006 (15) |
C7 | 0.055 (3) | 0.030 (2) | 0.032 (2) | −0.0052 (18) | 0.000 (2) | −0.0044 (16) |
C8 | 0.048 (3) | 0.038 (2) | 0.033 (2) | −0.0015 (18) | −0.0030 (19) | −0.0117 (18) |
C9 | 0.035 (2) | 0.049 (2) | 0.0200 (18) | −0.0015 (18) | −0.0026 (15) | −0.0052 (16) |
C10 | 0.0290 (19) | 0.0334 (19) | 0.0255 (19) | −0.0044 (15) | −0.0052 (15) | 0.0005 (15) |
C11 | 0.033 (2) | 0.0305 (18) | 0.0163 (16) | 0.0023 (15) | 0.0017 (15) | 0.0045 (13) |
C12 | 0.034 (2) | 0.0329 (19) | 0.0281 (19) | −0.0037 (16) | 0.0028 (16) | 0.0004 (16) |
C13 | 0.030 (2) | 0.048 (2) | 0.031 (2) | 0.0013 (17) | 0.0070 (17) | 0.0008 (17) |
C14 | 0.044 (2) | 0.041 (2) | 0.030 (2) | 0.0105 (19) | 0.0067 (18) | −0.0071 (17) |
C15 | 0.045 (3) | 0.040 (2) | 0.043 (2) | 0.0001 (19) | 0.003 (2) | −0.0177 (18) |
C16 | 0.033 (2) | 0.040 (2) | 0.035 (2) | −0.0030 (17) | 0.0015 (17) | −0.0079 (17) |
Geometric parameters (Å, º) top
S1—C1 | 1.772 (4) | C7—H7 | 0.9500 |
S1—S3 | 2.049 (2) | C8—C9 | 1.377 (6) |
S2—C1 | 1.772 (3) | C8—H8 | 0.9500 |
S2—S4 | 2.046 (2) | C9—C10 | 1.382 (5) |
S3—C2 | 1.780 (4) | C9—H9 | 0.9500 |
S4—C2 | 1.770 (4) | C10—H10 | 0.9500 |
Cl1—C3 | 1.754 (4) | C11—C12 | 1.382 (5) |
Cl2—C4 | 1.743 (4) | C11—C16 | 1.406 (5) |
C1—C3 | 1.341 (5) | C12—C13 | 1.391 (5) |
C2—C4 | 1.327 (5) | C12—H12 | 0.9500 |
C3—C5 | 1.460 (5) | C13—C14 | 1.380 (6) |
C4—C11 | 1.479 (5) | C13—H13 | 0.9500 |
C5—C6 | 1.392 (5) | C14—C15 | 1.383 (6) |
C5—C10 | 1.399 (5) | C14—H14 | 0.9500 |
C6—C7 | 1.388 (5) | C15—C16 | 1.369 (6) |
C6—H6 | 0.9500 | C15—H15 | 0.9500 |
C7—C8 | 1.386 (6) | C16—H16 | 0.9500 |
| | | |
C1—S1—S3 | 101.3 (1) | C9—C8—H8 | 120.1 |
C1—S2—S4 | 102.7 (1) | C7—C8—H8 | 120.1 |
C2—S3—S1 | 102.5 (1) | C8—C9—C10 | 120.5 (4) |
C2—S4—S2 | 101.8 (1) | C8—C9—H9 | 119.8 |
C3—C1—S1 | 123.0 (3) | C10—C9—H9 | 119.8 |
C3—C1—S2 | 120.5 (3) | C9—C10—C5 | 120.4 (3) |
S1—C1—S2 | 116.5 (2) | C9—C10—H10 | 119.8 |
C4—C2—S4 | 122.0 (3) | C5—C10—H10 | 119.8 |
C4—C2—S3 | 121.7 (3) | C12—C11—C16 | 118.9 (3) |
S4—C2—S3 | 116.2 (2) | C12—C11—C4 | 120.3 (3) |
C1—C3—C5 | 127.7 (3) | C16—C11—C4 | 120.8 (3) |
C1—C3—Cl1 | 116.6 (3) | C11—C12—C13 | 120.2 (4) |
C5—C3—Cl1 | 115.7 (3) | C11—C12—H12 | 119.9 |
C2—C4—C11 | 126.8 (4) | C13—C12—H12 | 119.9 |
C2—C4—Cl2 | 117.6 (3) | C14—C13—C12 | 120.4 (4) |
C11—C4—Cl2 | 115.6 (3) | C14—C13—H13 | 119.8 |
C6—C5—C10 | 118.8 (3) | C12—C13—H13 | 119.8 |
C6—C5—C3 | 120.4 (3) | C13—C14—C15 | 119.4 (4) |
C10—C5—C3 | 120.8 (3) | C13—C14—H14 | 120.3 |
C7—C6—C5 | 120.3 (4) | C15—C14—H14 | 120.3 |
C7—C6—H6 | 119.9 | C16—C15—C14 | 120.8 (4) |
C5—C6—H6 | 119.9 | C16—C15—H15 | 119.6 |
C8—C7—C6 | 120.2 (4) | C14—C15—H15 | 119.6 |
C8—C7—H7 | 119.9 | C15—C16—C11 | 120.2 (4) |
C6—C7—H7 | 119.9 | C15—C16—H16 | 119.9 |
C9—C8—C7 | 119.9 (4) | C11—C16—H16 | 119.9 |
| | | |
C1—S1—S3—C2 | 75.0 (2) | Cl1—C3—C5—C10 | 39.1 (4) |
C1—S2—S4—C2 | 74.5 (2) | C10—C5—C6—C7 | 2.4 (6) |
S3—S1—C1—C3 | 138.6 (3) | C3—C5—C6—C7 | −178.7 (4) |
S3—S1—C1—S2 | −41.0 (2) | C5—C6—C7—C8 | −0.9 (6) |
S4—S2—C1—C3 | 153.0 (3) | C6—C7—C8—C9 | −0.6 (7) |
S4—S2—C1—S1 | −27.4 (2) | C7—C8—C9—C10 | 0.4 (6) |
S2—S4—C2—C4 | 136.5 (3) | C8—C9—C10—C5 | 1.2 (6) |
S2—S4—C2—S3 | −40.3 (2) | C6—C5—C10—C9 | −2.6 (5) |
S1—S3—C2—C4 | 155.1 (3) | C3—C5—C10—C9 | 178.6 (3) |
S1—S3—C2—S4 | −28.2 (2) | C2—C4—C11—C12 | 48.5 (5) |
S1—C1—C3—C5 | 2.0 (6) | Cl2—C4—C11—C12 | −132.4 (3) |
S2—C1—C3—C5 | −178.3 (3) | C2—C4—C11—C16 | −132.4 (4) |
S1—C1—C3—Cl1 | −177.0 (2) | Cl2—C4—C11—C16 | 46.8 (4) |
S2—C1—C3—Cl1 | 2.7 (4) | C16—C11—C12—C13 | 1.1 (6) |
S4—C2—C4—C11 | −0.2 (5) | C4—C11—C12—C13 | −179.7 (3) |
S3—C2—C4—C11 | 176.3 (3) | C11—C12—C13—C14 | −0.9 (6) |
S4—C2—C4—Cl2 | −179.3 (2) | C12—C13—C14—C15 | 0.7 (6) |
S3—C2—C4—Cl2 | −2.8 (4) | C13—C14—C15—C16 | −0.7 (7) |
C1—C3—C5—C6 | 41.3 (6) | C14—C15—C16—C11 | 1.0 (7) |
Cl1—C3—C5—C6 | −139.7 (3) | C12—C11—C16—C15 | −1.2 (6) |
C1—C3—C5—C10 | −139.9 (4) | C4—C11—C16—C15 | 179.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···S2i | 0.95 | 2.91 | 3.616 (4) | 132 |
C14—H14···S2ii | 0.95 | 3.04 | 3.920 (4) | 155 |
C15—H15···S4iii | 0.95 | 3.02 | 3.710 (5) | 130 |
C9—H9···Cl2iv | 0.95 | 2.97 | 3.749 (4) | 140 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z+1; (iii) x+1/2, −y+3/2, −z+1; (iv) −x+3/2, −y+1, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C16H10Cl2S4 |
Mr | 401.38 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 133 |
a, b, c (Å) | 7.611 (4), 17.137 (5), 26.161 (10) |
V (Å3) | 3412 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.86 |
Crystal size (mm) | 0.6 × 0.4 × 0.4 |
|
Data collection |
Diffractometer | Stoe STADI-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2845, 2845, 2414 |
Rint | ? |
(sin θ/λ)max (Å−1) | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.140, 1.04 |
No. of reflections | 2845 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.46 |
Selected geometric parameters (Å, º) topS1—C1 | 1.772 (4) | S3—C2 | 1.780 (4) |
S1—S3 | 2.049 (2) | S4—C2 | 1.770 (4) |
S2—C1 | 1.772 (3) | C1—C3 | 1.341 (5) |
S2—S4 | 2.046 (2) | C2—C4 | 1.327 (5) |
| | | |
C1—S1—S3 | 101.3 (1) | C1—C3—C5 | 127.7 (3) |
C1—S2—S4 | 102.7 (1) | C1—C3—Cl1 | 116.6 (3) |
C2—S3—S1 | 102.5 (1) | C5—C3—Cl1 | 115.7 (3) |
C2—S4—S2 | 101.8 (1) | C2—C4—C11 | 126.8 (4) |
S1—C1—S2 | 116.5 (2) | C2—C4—Cl2 | 117.6 (3) |
S4—C2—S3 | 116.2 (2) | C11—C4—Cl2 | 115.6 (3) |
| | | |
C1—S1—S3—C2 | 75.0 (2) | S4—S2—C1—S1 | −27.4 (2) |
C1—S2—S4—C2 | 74.5 (2) | S2—S4—C2—S3 | −40.3 (2) |
S3—S1—C1—S2 | −41.0 (2) | S1—S3—C2—S4 | −28.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···S2i | 0.95 | 2.91 | 3.616 (4) | 132 |
C14—H14···S2ii | 0.95 | 3.04 | 3.920 (4) | 155 |
C15—H15···S4iii | 0.95 | 3.02 | 3.710 (5) | 130 |
C9—H9···Cl2iv | 0.95 | 2.97 | 3.749 (4) | 140 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z+1; (iii) x+1/2, −y+3/2, −z+1; (iv) −x+3/2, −y+1, z−1/2. |
The reaction of carbenes with CS2 is not well understood. Several diazo compounds and diazirines have been shown to react thermally (at room or elevated temperatures) with CS2 with loss of N2 and formation of 1,2,4,5-tetrathianes (Raasch, 1970; Schoenberg et al., 1962). Loss of nitrogen from the precursors used in these experiments leads to triplet carbenes; however, it is not clear if the carbenes or the precursors react with CS2. We therefore investigated the photochemical reaction of phenylchlorodiazirine (2), which is the precursor of the singlet carbene (1), with CS2.
At room temperature, a solution of (2) in CS2 becomes dark red within several hours, while at 238 K, these solutions are stable. UV irradiation (λ > 350 nm) at 238 K results in the formation of an intense red solution, from which the yellow title compound (3) can be isolated in 15% yield.
A plausible mechanism is shown in the Scheme. Photolysis of (2) results in the formation of carbene (1), which is trapped by CS2. The methylenedithiirane (4) might then ring-open (either photochemically or in a thermal equilibrium) to give biradical (5). Dimerization of (5) finally produces (3). However, there is no direct evidence for the intermediates (1), (4) and (5), and so the mechanism remains speculative.
The X-ray investigation of the product (3) confirmed the proposed structure, with a trans disposition of the methylene substituents (Fig. 1). Despite the formal symmetry of the chemical formula, the molecule shows no crystallographic symmetry. The tetrathiane ring displays a slightly distorted twist conformation with local twofold axes, one along the direction C1···C2 and the other between the midpoints of S1—S3 and S2—S4. The dimensions of the ring (Table 1) may be considered normal, and are closely similar to those of the only other bis(methylene)-substituted 1,2,4,5-tetrathiane found in a search of the Cambridge Structural Database (Version of October, 2001; Allen & Kennard, 1993), namely the bis(dimesitylmethylene) derivative (Selzer & Rappoport, 1996). The angles around the methylene C atoms, amongst which the C—C—C angles are much the largest, reflect the higher electronegativity of the chlorine substituents.
The crystal packing shows two types of short contacts, three possible weak hydrogen bonds C—H···S and one C—H···Cl (Table 2), and a Cl2···Cl2 contact [symmetry code: 2 - x, 1 - y, 1 - z; Cl···Cl 3.475 (2) Å and C—Cl···Cl 132.01 (14)°]. We note, however, that the hydrogen bonds represent at best borderline cases, cf. sum of van der Waals radii H + Cl = 2.95 Å and H+S = 3.00 Å (Bondi, 1964).