organic compounds
2-Chloroethyl ethyl sulfide (Cl-CH2-CH2-S-CH2-CH3 or C4H9ClS) is used as an analogue for mustard gas in biomedical studies. The Cl-C-C-S and the two C-C-S-C torsion angles are -177.38 (9), 83.17 (14) and 73.81 (16)°, respectively, and are similar to values that have been predicted, by ab initio quantum calculations, for the corresponding parameters in mustard gas. There are no strong intermolecular interactions, and the packing in the crystal structure bears some resemblance to hexagonal close packing.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804000753/ya6195sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804000753/ya6195Isup2.hkl |
CCDC reference: 234874
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Watkin et al., 2003); molecular graphics: XP (Sheldrick, 1997); software used to prepare material for publication: CRYSTALS, enCIFer (CCDC, 2002), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
2-Chloroethyl ethyl sulfide top
Crystal data top
C4H9ClS | F(000) = 264 |
Mr = 124.63 | Dx = 1.287 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3540 reflections |
a = 15.343 (3) Å | θ = 3–29° |
b = 8.5760 (14) Å | µ = 0.78 mm−1 |
c = 4.8863 (8) Å | T = 150 K |
V = 642.96 (18) Å3 | Cylinder, colourless |
Z = 4 | 1.00 × 0.30 × 0.30 mm |
Data collection top
Bruker SMART APEX diffractometer | 1313 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.03 |
ω scans | θmax = 28.3°, θmin = 2.7° |
Absorption correction: multi-scan SADABS (Sheldrick, 2002) | h = −19→19 |
Tmin = 0.352, Tmax = 0.790 | k = −9→11 |
4048 measured reflections | l = −6→6 |
1441 independent reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0194P)2 + 0.136P] where P = (Fo2 + 2Fc2)/3 (SHELXL97; Sheldrick, 1997) |
S = 1.01 | (Δ/σ)max = 0.001 |
1438 reflections | Δρmax = 0.36 e Å−3 |
56 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack (1983); 597 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.23 (12) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.44869 (3) | 0.12110 (5) | 0.13095 (14) | 0.0353 | |
C2 | 0.37514 (12) | 0.1959 (2) | 0.3892 (4) | 0.0315 | |
C3 | 0.32202 (11) | 0.0630 (2) | 0.5064 (4) | 0.0276 | |
S4 | 0.24368 (3) | 0.13448 (5) | 0.75570 (15) | 0.0359 | |
C5 | 0.15538 (12) | 0.1954 (2) | 0.5312 (4) | 0.0379 | |
C6 | 0.10405 (12) | 0.0620 (3) | 0.4094 (5) | 0.0441 | |
H21 | 0.4096 | 0.2463 | 0.5388 | 0.0377* | |
H22 | 0.3352 | 0.2745 | 0.3049 | 0.0377* | |
H31 | 0.3621 | −0.0130 | 0.5975 | 0.0331* | |
H32 | 0.2901 | 0.0096 | 0.3545 | 0.0331* | |
H51 | 0.1145 | 0.2622 | 0.6391 | 0.0455* | |
H52 | 0.1809 | 0.2579 | 0.3780 | 0.0455* | |
H61 | 0.0569 | 0.1043 | 0.2890 | 0.0529* | |
H62 | 0.0774 | −0.0012 | 0.5598 | 0.0529* | |
H63 | 0.1438 | −0.0055 | 0.2987 | 0.0529* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0313 (2) | 0.0445 (2) | 0.0302 (2) | 0.00303 (18) | 0.0016 (2) | −0.0013 (2) |
C2 | 0.0350 (9) | 0.0308 (9) | 0.0286 (9) | 0.0011 (7) | 0.0035 (8) | −0.0035 (8) |
C3 | 0.0295 (8) | 0.0270 (8) | 0.0263 (8) | 0.0039 (6) | −0.0012 (8) | −0.0022 (7) |
S4 | 0.0336 (2) | 0.0474 (3) | 0.0268 (2) | 0.0031 (2) | 0.0006 (2) | −0.0039 (3) |
C5 | 0.0326 (9) | 0.0307 (9) | 0.0505 (12) | 0.0075 (8) | −0.0020 (9) | −0.0017 (8) |
C6 | 0.0307 (10) | 0.0419 (11) | 0.0598 (15) | 0.0010 (8) | −0.0077 (11) | −0.0026 (10) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.810 (2) | S4—C5 | 1.820 (2) |
C2—H22 | 1.000 | C5—H52 | 1.000 |
C2—H21 | 1.000 | C5—H51 | 1.000 |
C2—C3 | 1.513 (3) | C5—C6 | 1.512 (3) |
C3—H32 | 1.000 | C6—H63 | 1.000 |
C3—H31 | 1.000 | C6—H62 | 1.000 |
C3—S4 | 1.818 (2) | C6—H61 | 1.000 |
H22—C2—H21 | 109.467 | H52—C5—H51 | 109.466 |
H22—C2—C3 | 109.481 | H52—C5—C6 | 108.313 |
H21—C2—C3 | 109.481 | H51—C5—C6 | 108.313 |
H22—C2—Cl1 | 109.482 | H52—C5—S4 | 108.313 |
H21—C2—Cl1 | 109.482 | H51—C5—S4 | 108.314 |
C3—C2—Cl1 | 109.43 (12) | C6—C5—S4 | 114.06 (14) |
H32—C3—H31 | 109.467 | H63—C6—H62 | 109.476 |
H32—C3—S4 | 109.131 | H63—C6—H61 | 109.475 |
H31—C3—S4 | 109.131 | H62—C6—H61 | 109.476 |
H32—C3—C2 | 109.131 | H63—C6—C5 | 109.466 |
H31—C3—C2 | 109.131 | H62—C6—C5 | 109.467 |
S4—C3—C2 | 110.83 (12) | H61—C6—C5 | 109.467 |
C5—S4—C3 | 100.67 (10) | ||
C5—S4—C3—C2 | 83.17 (14) | Cl1—C2—C3—S4 | −177.38 (9) |
C3—S4—C5—C6 | 73.81 (16) |