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The unequivocal structure of dichloromethyl phenyl sulfone, C
7H
6Cl
2O
2S, (I),
via X-ray analysis is reported for the first time. Prepared from the reaction of sodium benzenesulfinate with chloroform in KOH, (I) exhibited a sharp melting point, 331.5–332.0 K. Several different melting points have been reported. We find that (I) crystallizes as two chemically identical molecules in the asymmetric unit, but with a number of small geometric differences between the two molecules. Intermolecular Cl
2C—H
O—S(O)—Ph hydrogen bonding between the two geometrically different molecules produces infinite molecular chains, which may induce the small geometric differences exhibited in the two molecules of (I).
Supporting information
CCDC reference: 189310
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.032
- wR factor = 0.088
- Data-to-parameter ratio = 15.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation,1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON.
dichloromethyl phenyl sulfone
top
Crystal data top
C7H6Cl2O2S | Dx = 1.604 Mg m−3 |
Mr = 225.09 | Melting point = 331.5–332 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 10.353 (3) Å | Cell parameters from 25 reflections |
b = 9.5269 (10) Å | θ = 13.7–16.2° |
c = 18.9124 (18) Å | µ = 0.87 mm−1 |
β = 91.541 (14)° | T = 296 K |
V = 1864.6 (7) Å3 | Prism, colorless |
Z = 8 | 0.41 × 0.35 × 0.30 mm |
F(000) = 912 | |
Data collection top
Rigaku AFC-5S diffractometer | 2137 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.1°, θmin = 2.0° |
ω scans | h = 0→12 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.723, Tmax = 0.769 | l = −22→22 |
3501 measured reflections | 3 standard reflections every 100 reflections |
3305 independent reflections | intensity decay: 0.9% |
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)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0253P)2 + 0.876P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3305 reflections | Δρmax = 0.21 e Å−3 |
218 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0119 (5) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.66005 (9) | 0.57739 (10) | 0.46637 (5) | 0.0732 (3) | |
Cl2 | 0.58109 (10) | 0.43312 (10) | 0.33756 (6) | 0.0848 (3) | |
S1 | 0.67094 (7) | 0.71983 (8) | 0.32793 (4) | 0.0485 (2) | |
O1 | 0.5951 (2) | 0.7304 (2) | 0.26412 (11) | 0.0693 (6) | |
O2 | 0.80360 (19) | 0.6788 (2) | 0.32532 (11) | 0.0615 (6) | |
C1 | 0.6578 (3) | 0.8747 (3) | 0.37739 (15) | 0.0469 (7) | |
C2 | 0.5494 (3) | 0.9579 (3) | 0.36768 (17) | 0.0605 (9) | |
C3 | 0.5393 (4) | 1.0783 (4) | 0.4078 (2) | 0.0755 (10) | |
C4 | 0.6349 (4) | 1.1127 (4) | 0.4562 (2) | 0.0767 (11) | |
C5 | 0.7418 (4) | 1.0299 (4) | 0.46509 (18) | 0.0704 (10) | |
C6 | 0.7553 (3) | 0.9104 (3) | 0.42558 (17) | 0.0594 (8) | |
C7 | 0.5861 (3) | 0.5934 (3) | 0.38229 (16) | 0.0520 (8) | |
Cl1a | 0.20410 (11) | 0.63129 (11) | 0.22819 (5) | 0.0842 (3) | |
Cl2a | 0.12902 (11) | 0.90469 (10) | 0.27820 (6) | 0.0883 (3) | |
S1a | 0.15960 (7) | 0.67724 (9) | 0.37831 (4) | 0.0509 (2) | |
O1a | 0.0773 (2) | 0.7571 (2) | 0.42241 (10) | 0.0649 (6) | |
O2a | 0.2965 (2) | 0.6945 (3) | 0.38559 (13) | 0.0725 (7) | |
C1a | 0.1210 (3) | 0.4986 (3) | 0.38389 (14) | 0.0489 (7) | |
C2a | 0.0006 (3) | 0.4623 (4) | 0.40854 (15) | 0.0582 (8) | |
C3a | −0.0311 (4) | 0.3218 (4) | 0.41355 (18) | 0.0705 (10) | |
C4a | 0.0552 (4) | 0.2210 (4) | 0.39426 (18) | 0.0751 (10) | |
C5a | 0.1738 (4) | 0.2579 (4) | 0.3692 (2) | 0.0755 (10) | |
C6a | 0.2082 (3) | 0.3969 (4) | 0.36406 (17) | 0.0630 (9) | |
C7a | 0.1111 (3) | 0.7233 (3) | 0.28827 (15) | 0.0533 (8) | |
H2 | 0.4847 | 0.9334 | 0.3349 | 0.073* | |
H3 | 0.4675 | 1.1361 | 0.4020 | 0.091* | |
H4 | 0.6270 | 1.1935 | 0.4834 | 0.092* | |
H5 | 0.8059 | 1.0547 | 0.4982 | 0.084* | |
H6 | 0.8285 | 0.8545 | 0.4311 | 0.071* | |
H7 | 0.4973 | 0.6263 | 0.3879 | 0.062* | |
H2a | −0.0578 | 0.5313 | 0.4215 | 0.070* | |
H3a | −0.1114 | 0.2956 | 0.4301 | 0.085* | |
H4a | 0.0334 | 0.1267 | 0.3981 | 0.090* | |
H5a | 0.2311 | 0.1884 | 0.3557 | 0.091* | |
H6a | 0.2887 | 0.4221 | 0.3475 | 0.076* | |
H7a | 0.0200 | 0.6985 | 0.2804 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0758 (6) | 0.0843 (7) | 0.0593 (5) | −0.0112 (5) | −0.0031 (4) | 0.0180 (5) |
Cl2 | 0.1002 (8) | 0.0528 (5) | 0.1018 (8) | −0.0144 (5) | 0.0109 (6) | −0.0181 (5) |
S1 | 0.0493 (4) | 0.0500 (4) | 0.0461 (4) | −0.0005 (4) | −0.0010 (3) | −0.0006 (4) |
O1 | 0.0840 (16) | 0.0756 (16) | 0.0474 (12) | 0.0067 (13) | −0.0149 (11) | −0.0021 (11) |
O2 | 0.0462 (12) | 0.0671 (15) | 0.0715 (14) | 0.0024 (11) | 0.0107 (10) | −0.0023 (12) |
C1 | 0.0481 (17) | 0.0435 (17) | 0.0491 (17) | −0.0056 (14) | 0.0013 (13) | 0.0028 (14) |
C2 | 0.057 (2) | 0.057 (2) | 0.067 (2) | 0.0013 (17) | −0.0032 (16) | 0.0032 (17) |
C3 | 0.075 (2) | 0.052 (2) | 0.100 (3) | 0.0071 (19) | 0.011 (2) | −0.003 (2) |
C4 | 0.108 (3) | 0.049 (2) | 0.074 (2) | −0.012 (2) | 0.016 (2) | −0.0108 (18) |
C5 | 0.092 (3) | 0.056 (2) | 0.063 (2) | −0.022 (2) | −0.0102 (19) | −0.0045 (18) |
C6 | 0.059 (2) | 0.054 (2) | 0.065 (2) | −0.0089 (16) | −0.0082 (16) | 0.0028 (16) |
C7 | 0.0425 (17) | 0.0509 (18) | 0.0625 (19) | −0.0045 (14) | 0.0013 (14) | −0.0017 (15) |
Cl1a | 0.1148 (8) | 0.0822 (7) | 0.0569 (5) | 0.0216 (6) | 0.0302 (5) | −0.0024 (5) |
Cl2a | 0.1195 (9) | 0.0564 (6) | 0.0896 (7) | 0.0057 (5) | 0.0115 (6) | 0.0075 (5) |
S1a | 0.0448 (4) | 0.0604 (5) | 0.0472 (4) | −0.0025 (4) | −0.0034 (3) | −0.0085 (4) |
O1a | 0.0683 (14) | 0.0765 (16) | 0.0502 (12) | 0.0007 (12) | 0.0076 (11) | −0.0200 (11) |
O2a | 0.0441 (12) | 0.0804 (17) | 0.0923 (17) | −0.0070 (12) | −0.0118 (11) | −0.0081 (14) |
C1a | 0.0485 (17) | 0.061 (2) | 0.0370 (15) | −0.0021 (15) | −0.0081 (13) | 0.0007 (14) |
C2a | 0.063 (2) | 0.069 (2) | 0.0430 (17) | −0.0009 (18) | 0.0048 (15) | 0.0024 (16) |
C3a | 0.074 (2) | 0.078 (3) | 0.060 (2) | −0.013 (2) | 0.0097 (18) | 0.0068 (19) |
C4a | 0.097 (3) | 0.060 (2) | 0.068 (2) | −0.009 (2) | −0.006 (2) | 0.0087 (19) |
C5a | 0.078 (3) | 0.065 (3) | 0.082 (3) | 0.011 (2) | −0.012 (2) | −0.002 (2) |
C6a | 0.054 (2) | 0.067 (2) | 0.067 (2) | 0.0019 (18) | −0.0037 (16) | −0.0027 (18) |
C7a | 0.0588 (19) | 0.0525 (18) | 0.0488 (17) | −0.0007 (16) | 0.0048 (14) | −0.0029 (15) |
Geometric parameters (Å, º) top
Cl1—C7 | 1.753 (3) | C3—C4 | 1.370 (5) |
Cl1a—C7a | 1.745 (3) | C3a—C4a | 1.367 (5) |
Cl2—C7 | 1.746 (3) | C4—C5 | 1.366 (5) |
Cl2a—C7a | 1.749 (3) | C4a—C5a | 1.373 (5) |
S1—O1 | 1.425 (2) | C5—C6 | 1.370 (4) |
S1a—O1a | 1.428 (2) | C5a—C6a | 1.376 (5) |
S1—O2 | 1.430 (2) | C2—H2 | 0.9300 |
S1a—O2a | 1.429 (2) | C2a—H2a | 0.9300 |
S1—C1 | 1.754 (3) | C3—H3 | 0.9300 |
S1a—C1a | 1.752 (3) | C3a—H3a | 0.9300 |
S1—C7 | 1.824 (3) | C4—H4 | 0.9300 |
S1a—C7a | 1.816 (3) | C4a—H4a | 0.9300 |
C1—C2 | 1.382 (4) | C5—H5 | 0.9300 |
C1a—C2a | 1.386 (4) | C5a—H5a | 0.9300 |
C1—C6 | 1.384 (4) | C6—H6 | 0.9300 |
C1a—C6a | 1.383 (4) | C6a—H6a | 0.9300 |
C2—C3 | 1.381 (5) | C7—H7 | 0.9800 |
C2a—C3a | 1.383 (5) | C7a—H7a | 0.9800 |
| | | |
O1—S1—O2 | 119.83 (14) | Cl2—C7—S1 | 108.24 (16) |
O1a—S1a—O2a | 119.20 (14) | Cl2a—C7a—S1a | 108.26 (16) |
O1—S1—C1 | 110.07 (14) | Cl1—C7—S1 | 111.31 (16) |
O1a—S1a—C1a | 109.97 (14) | Cl1a—C7a—S1a | 110.25 (17) |
O2—S1—C1 | 109.68 (14) | C3—C2—H2 | 120.8 |
O2a—S1a—C1a | 109.47 (15) | C1—C2—H2 | 120.8 |
O1—S1—C7 | 105.14 (14) | C3a—C2a—H2a | 120.6 |
O1a—S1a—C7a | 105.37 (14) | C1a—C2a—H2a | 120.6 |
O2—S1—C7 | 108.45 (14) | C4—C3—H3 | 119.9 |
O2a—S1a—C7a | 108.09 (15) | C2—C3—H3 | 119.9 |
C1—S1—C7 | 102.10 (13) | C4a—C3a—H3a | 119.9 |
C1a—S1a—C7a | 103.49 (14) | C2a—C3a—H3a | 119.9 |
C2—C1—C6 | 121.4 (3) | C5—C4—H4 | 119.6 |
C2a—C1a—C6a | 121.0 (3) | C3—C4—H4 | 119.6 |
C2—C1—S1 | 119.1 (2) | C3a—C4a—H4a | 119.7 |
C2a—C1a—S1a | 118.1 (3) | C5a—C4a—H4a | 119.7 |
C6—C1—S1 | 119.5 (2) | C4—C5—H5 | 119.8 |
C6a—C1a—S1a | 120.8 (2) | C6—C5—H5 | 119.8 |
C3—C2—C1 | 118.4 (3) | C4a—C5a—H5a | 119.8 |
C3a—C2a—C1a | 118.8 (3) | C6a—C5a—H5a | 119.8 |
C4—C3—C2 | 120.2 (4) | C5—C6—H6 | 120.6 |
C4a—C3a—C2a | 120.2 (3) | C1—C6—H6 | 120.6 |
C5—C4—C3 | 120.8 (3) | C5a—C6a—H6a | 120.6 |
C5a—C4a—C3a | 120.6 (4) | C1a—C6a—H6a | 120.6 |
C4—C5—C6 | 120.4 (3) | Cl2—C7—H7 | 108.5 |
C4a—C5a—C6a | 120.4 (4) | Cl1—C7—H7 | 108.5 |
C5—C6—C1 | 118.7 (3) | S1—C7—H7 | 108.5 |
C5a—C6a—C1a | 118.9 (3) | Cl1a—C7a—H7a | 109.0 |
Cl2—C7—Cl1 | 111.72 (17) | Cl2a—C7a—H7a | 109.0 |
Cl2a—C7a—Cl1a | 111.32 (17) | S1a—C7a—H7a | 109.0 |
| | | |
O1—S1—C1—C2 | 24.6 (3) | C3—C4—C5—C6 | 0.0 (6) |
O1a—S1a—C1a—C2a | 19.7 (3) | C3a—C4a—C5a—C6a | 0.9 (6) |
O2—S1—C1—C2 | 158.5 (2) | C4—C5—C6—C1 | −0.8 (5) |
O2a—S1a—C1a—C2a | 152.4 (2) | C4a—C5a—C6a—C1a | −0.6 (5) |
C7—S1—C1—C2 | −86.6 (3) | C2—C1—C6—C5 | 1.1 (5) |
C7a—S1a—C1a—C2a | −92.5 (2) | C2a—C1a—C6a—C5a | −0.1 (5) |
O1—S1—C1—C6 | −155.9 (2) | S1—C1—C6—C5 | −178.3 (2) |
O1a—S1a—C1a—C6a | −160.5 (2) | S1a—C1a—C6a—C5a | −179.9 (3) |
O2—S1—C1—C6 | −22.1 (3) | O1—S1—C7—Cl2 | 61.40 (19) |
O2a—S1a—C1a—C6a | −27.7 (3) | O1a—S1a—C7a—Cl2a | 58.43 (19) |
C7—S1—C1—C6 | 92.8 (3) | O2—S1—C7—Cl2 | −67.91 (18) |
C7a—S1a—C1a—C6a | 87.3 (3) | O2a—S1a—C7a—Cl2a | −70.04 (19) |
C6—C1—C2—C3 | −0.5 (5) | C1—S1—C7—Cl2 | 176.34 (16) |
C6a—C1a—C2a—C3a | 0.4 (4) | C1a—S1a—C7a—Cl2a | 173.91 (16) |
S1—C1—C2—C3 | 178.9 (3) | O1—S1—C7—Cl1 | −175.45 (16) |
S1a—C1a—C2a—C3a | −179.7 (2) | O1a—S1a—C7a—Cl1a | −179.58 (16) |
C1—C2—C3—C4 | −0.4 (5) | O2—S1—C7—Cl1 | 55.2 (2) |
C1a—C2a—C3a—C4a | −0.2 (5) | O2a—S1a—C7a—Cl1a | 51.9 (2) |
C2—C3—C4—C5 | 0.7 (6) | C1—S1—C7—Cl1 | −60.51 (19) |
C2a—C3a—C4a—C5a | −0.5 (5) | C1a—S1a—C7a—Cl1a | −64.10 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2a | 0.98 | 2.18 | 3.151 (4) | 172 |
C7a—H7a···O2i | 0.98 | 2.42 | 3.305 (4) | 149 |
Symmetry code: (i) x−1, y, z. |
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