




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808037355/hg2443sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808037355/hg2443Isup2.hkl |
CCDC reference: 713273
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.061
- wR factor = 0.211
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14A PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14B PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C12 - C13 ... 1.38 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C15 - C16 ... 1.38 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C4 .. 2.97 Ang.
Alert level G PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 8.00 Deg. C14A -CL1 -H14B 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 8.00 Deg. C14B -CL1 -H14B 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 8.00 Deg. CL1 -C14A -H14B 1.555 1.555 1.555 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 8.00 Deg. CL1 -C14B -H14B 1.555 1.555 1.555 PLAT793_ALERT_4_G The Model has Chirality at C2 (Verify) .... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of cis-2-(4-chlorophenyl)-6-phenyldithian-4-one (3.18 g, 0.01 mol), diethyl ether (60 ml), bromine (3.0 g) in water (30 ml) was shaken for few minutes. The solid that separated was filtered, washed with ether and recrystallized from chloroform-carbon tetrachloride mixture (1:1 v/v). The yield obtained was 68%(2.16 g).
The structure was solved in the space group Pnma with half a molecule in the asymmetric unit. The other half is related by a mirror plane symmetry [x, 1/2 - y, z]. The s.o.f. of C14A, Cl1, C14B and H14B is 0.5 and for the remaining phenyl group atoms it is 1.00. This confirms the (p-chloro)phenyl group at 2 position and the phenyl group at 6 position. The H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.93–0.98 Å and Uiso = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-NT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C17H15ClO2S | Dx = 1.366 Mg m−3 |
Mr = 318.81 | Melting point: 417 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 9562 reflections |
a = 11.5195 (5) Å | θ = 3.0–24.8° |
b = 25.7589 (12) Å | µ = 0.38 mm−1 |
c = 5.2248 (2) Å | T = 296 K |
V = 1550.35 (12) Å3 | Thick, colourless |
Z = 4 | 0.58 × 0.35 × 0.15 mm |
F(000) = 664 |
Bruker APEXII CCD diffractometer | 1954 independent reflections |
Radiation source: fine-focus sealed tube | 1551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 0 pixels mm-1 | θmax = 28.3°, θmin = 1.6° |
ϕ and ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −34→34 |
Tmin = 0.809, Tmax = 0.945 | l = −6→6 |
33450 measured reflections |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.20 | w = 1/[σ2(Fo2) + (0.0825P)2 + 1.5305P] where P = (Fo2 + 2Fc2)/3 |
1954 reflections | (Δ/σ)max = 0.001 |
106 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C17H15ClO2S | V = 1550.35 (12) Å3 |
Mr = 318.81 | Z = 4 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 11.5195 (5) Å | µ = 0.38 mm−1 |
b = 25.7589 (12) Å | T = 296 K |
c = 5.2248 (2) Å | 0.58 × 0.35 × 0.15 mm |
Bruker APEXII CCD diffractometer | 1954 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1551 reflections with I > 2σ(I) |
Tmin = 0.809, Tmax = 0.945 | Rint = 0.040 |
33450 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.20 | Δρmax = 0.32 e Å−3 |
1954 reflections | Δρmin = −0.42 e Å−3 |
106 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 > 2σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.0955 (4) | 0.00160 (11) | 0.0431 (9) | 0.1475 (18) | 0.500 |
S1 | 0.24636 (8) | 0.25000 | 0.27287 (17) | 0.0434 (3) | |
O1 | 0.3171 (3) | 0.25000 | 0.0330 (5) | 0.0614 (10) | |
O4 | 0.5597 (3) | 0.25000 | 0.7542 (7) | 0.0772 (13) | |
C2 | 0.3029 (3) | 0.19728 (12) | 0.4726 (5) | 0.0477 (9) | |
C3 | 0.4354 (3) | 0.20065 (15) | 0.4859 (7) | 0.0621 (13) | |
C4 | 0.4819 (3) | 0.25000 | 0.5959 (8) | 0.0581 (16) | |
C11 | 0.2583 (3) | 0.14695 (14) | 0.3651 (7) | 0.0593 (11) | |
C12 | 0.1618 (4) | 0.12411 (19) | 0.4657 (10) | 0.0873 (18) | |
C13 | 0.1167 (5) | 0.0784 (2) | 0.3692 (16) | 0.113 (3) | |
C14A | 0.1685 (7) | 0.0557 (2) | 0.1666 (16) | 0.112 (3) | 0.500 |
C14B | 0.1685 (7) | 0.0557 (2) | 0.1666 (16) | 0.112 (3) | 0.500 |
C15 | 0.2634 (7) | 0.0778 (3) | 0.0566 (14) | 0.124 (3) | |
C16 | 0.3087 (5) | 0.1234 (2) | 0.1524 (10) | 0.0940 (19) | |
H2 | 0.27192 | 0.20147 | 0.64603 | 0.0573* | |
H3A | 0.46377 | 0.17188 | 0.58808 | 0.0745* | |
H3B | 0.46629 | 0.19651 | 0.31439 | 0.0745* | |
H12 | 0.12502 | 0.13981 | 0.60394 | 0.1053* | |
H13 | 0.05139 | 0.06340 | 0.44321 | 0.1358* | |
H14B | 0.13910 | 0.02476 | 0.10157 | 0.1344* | 0.500 |
H15 | 0.29807 | 0.06199 | −0.08411 | 0.1492* | |
H16 | 0.37304 | 0.13854 | 0.07466 | 0.1130* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.168 (3) | 0.0895 (18) | 0.185 (4) | −0.0163 (19) | −0.060 (3) | −0.035 (2) |
S1 | 0.0328 (5) | 0.0708 (7) | 0.0265 (5) | 0.0000 | −0.0033 (3) | 0.0000 |
O1 | 0.0611 (19) | 0.101 (2) | 0.0221 (13) | 0.0000 | 0.0046 (13) | 0.0000 |
O4 | 0.0365 (16) | 0.138 (3) | 0.057 (2) | 0.0000 | −0.0168 (14) | 0.0000 |
C2 | 0.0413 (14) | 0.0715 (18) | 0.0304 (13) | 0.0054 (13) | −0.0019 (11) | 0.0014 (12) |
C3 | 0.0390 (15) | 0.096 (3) | 0.0512 (18) | 0.0139 (16) | −0.0103 (13) | −0.0018 (17) |
C4 | 0.0304 (19) | 0.106 (4) | 0.038 (2) | 0.0000 | −0.0045 (16) | 0.0000 |
C11 | 0.0562 (18) | 0.069 (2) | 0.0527 (18) | 0.0096 (16) | −0.0125 (15) | 0.0000 (15) |
C12 | 0.063 (2) | 0.095 (3) | 0.104 (4) | −0.007 (2) | 0.009 (2) | −0.018 (3) |
C13 | 0.092 (4) | 0.097 (4) | 0.150 (6) | −0.019 (3) | −0.005 (4) | −0.004 (4) |
C14A | 0.118 (5) | 0.080 (3) | 0.138 (5) | −0.001 (3) | −0.048 (4) | −0.017 (3) |
C14B | 0.118 (5) | 0.080 (3) | 0.138 (5) | −0.001 (3) | −0.048 (4) | −0.017 (3) |
C15 | 0.156 (6) | 0.099 (4) | 0.118 (5) | 0.008 (4) | −0.006 (4) | −0.045 (4) |
C16 | 0.111 (4) | 0.094 (3) | 0.077 (3) | −0.001 (3) | 0.013 (3) | −0.025 (3) |
Cl1—C14A | 1.751 (7) | C13—C14B | 1.349 (11) |
Cl1—C14B | 1.751 (7) | C14A—C15 | 1.360 (11) |
Cl1—H14B | 0.8400 | C14B—C15 | 1.360 (11) |
S1—C2 | 1.832 (3) | C15—C16 | 1.379 (9) |
S1—C2i | 1.832 (3) | C2—H2 | 0.9800 |
S1—O1 | 1.495 (3) | C3—H3A | 0.9700 |
O4—C4 | 1.220 (5) | C3—H3B | 0.9700 |
C2—C3 | 1.530 (5) | C12—H12 | 0.9300 |
C2—C11 | 1.503 (5) | C13—H13 | 0.9300 |
C3—C4 | 1.494 (4) | C14A—H14B | 0.9300 |
C11—C12 | 1.363 (6) | C14B—H14B | 0.9300 |
C11—C16 | 1.393 (6) | C15—H15 | 0.9300 |
C12—C13 | 1.382 (8) | C16—H16 | 0.9300 |
C13—C14A | 1.349 (11) | ||
Cl1···C15ii | 3.645 (9) | C2···O1xiv | 3.232 (4) |
Cl1···H15iii | 2.8200 | C2···O1x | 3.232 (4) |
S1···O4iv | 3.494 (4) | C3···O1xiv | 3.412 (4) |
S1···O4v | 3.276 (4) | C3···O1x | 3.412 (4) |
S1···C4iv | 3.605 (4) | C4···S1xii | 3.605 (4) |
S1···O4vi | 3.494 (4) | C4···O1xiv | 2.970 (5) |
S1···O4vii | 3.276 (4) | C4···S1xv | 3.605 (4) |
S1···C4vi | 3.605 (4) | C4···O1x | 2.970 (5) |
O1···O4viii | 3.152 (5) | C12···C15xiv | 3.511 (9) |
O1···C2viii | 3.232 (4) | C15···C12viii | 3.511 (9) |
O1···C3viii | 3.412 (4) | C15···Cl1iii | 3.645 (9) |
O1···C4viii | 2.970 (5) | C16···O1 | 3.322 (5) |
O1···C16 | 3.322 (5) | C3···H16 | 2.7700 |
O1···C2ix | 3.232 (4) | C16···H3B | 2.7500 |
O1···C3ix | 3.412 (4) | H2···O1xiv | 2.4300 |
O1···O4ix | 3.152 (5) | H2···H12 | 2.3300 |
O1···C16i | 3.322 (5) | H2···O4v | 2.7900 |
O1···C4ix | 2.970 (5) | H2···O4vii | 2.7900 |
O4···O1x | 3.152 (5) | H2···O1x | 2.4300 |
O4···S1xi | 3.276 (4) | H2···H2i | 2.5000 |
O4···S1xii | 3.494 (4) | H3A···H12xi | 2.5900 |
O4···S1xiii | 3.276 (4) | H3B···O1 | 2.6500 |
O4···O1xiv | 3.152 (5) | H3B···C16 | 2.7500 |
O4···S1xv | 3.494 (4) | H3B···H16 | 2.2300 |
O1···H3Bi | 2.6500 | H12···H2 | 2.3300 |
O1···H2viii | 2.4300 | H12···H3Avii | 2.5900 |
O1···H2ix | 2.4300 | H15···Cl1ii | 2.8200 |
O1···H3B | 2.6500 | H16···C3 | 2.7700 |
O4···H2xiii | 2.7900 | H16···H3B | 2.2300 |
O4···H2xi | 2.7900 | ||
C14A—Cl1—H14B | 8.00 | C11—C16—C15 | 120.2 (5) |
C14B—Cl1—H14B | 8.00 | S1—C2—H2 | 108.00 |
C2—S1—C2i | 95.66 (14) | C3—C2—H2 | 108.00 |
O1—S1—C2 | 106.48 (13) | C11—C2—H2 | 108.00 |
O1—S1—C2i | 106.48 (13) | C2—C3—H3A | 109.00 |
C3—C2—C11 | 114.0 (3) | C2—C3—H3B | 109.00 |
S1—C2—C3 | 109.8 (2) | C4—C3—H3A | 109.00 |
S1—C2—C11 | 107.8 (2) | C4—C3—H3B | 108.00 |
C2—C3—C4 | 115.0 (3) | H3A—C3—H3B | 108.00 |
C3—C4—C3i | 116.6 (3) | C11—C12—H12 | 119.00 |
O4—C4—C3 | 121.62 (19) | C13—C12—H12 | 119.00 |
O4—C4—C3i | 121.62 (19) | C12—C13—H13 | 120.00 |
C12—C11—C16 | 117.4 (4) | C14A—C13—H13 | 120.00 |
C2—C11—C16 | 122.1 (4) | C14B—C13—H13 | 120.00 |
C2—C11—C12 | 120.5 (3) | Cl1—C14A—H14B | 8.00 |
C11—C12—C13 | 122.2 (5) | C13—C14A—H14B | 120.00 |
C12—C13—C14A | 119.3 (6) | C15—C14A—H14B | 120.00 |
C12—C13—C14B | 119.3 (6) | Cl1—C14B—H14B | 8.00 |
Cl1—C14A—C15 | 124.3 (6) | C13—C14B—H14B | 120.00 |
Cl1—C14A—C13 | 115.0 (6) | C15—C14B—H14B | 120.00 |
C13—C14A—C15 | 120.4 (6) | C14A—C15—H15 | 120.00 |
Cl1—C14B—C15 | 124.3 (6) | C14B—C15—H15 | 120.00 |
C13—C14B—C15 | 120.4 (6) | C16—C15—H15 | 120.00 |
Cl1—C14B—C13 | 115.0 (6) | C11—C16—H16 | 120.00 |
C14A—C15—C16 | 120.5 (7) | C15—C16—H16 | 120.00 |
C14B—C15—C16 | 120.5 (7) | ||
O1—S1—C2—C3 | 48.2 (2) | C2—C11—C16—C15 | −178.6 (5) |
O1—S1—C2—C11 | −76.5 (2) | C12—C11—C16—C15 | −2.2 (7) |
C2i—S1—C2—C3 | −60.9 (2) | C11—C12—C13—C14A | −0.9 (9) |
C2i—S1—C2—C11 | 174.5 (2) | C11—C12—C13—C14B | −0.9 (9) |
S1—C2—C3—C4 | 59.9 (3) | C12—C13—C14A—Cl1 | −174.1 (5) |
C11—C2—C3—C4 | −179.1 (3) | C12—C13—C14A—C15 | −0.7 (11) |
S1—C2—C11—C12 | −96.7 (4) | C12—C13—C14B—Cl1 | −174.1 (5) |
S1—C2—C11—C16 | 79.6 (4) | C12—C13—C14B—C15 | −0.7 (11) |
C3—C2—C11—C12 | 141.3 (4) | Cl1—C14A—C15—C16 | 173.5 (6) |
C3—C2—C11—C16 | −42.5 (5) | C13—C14A—C15—C16 | 0.7 (11) |
C2—C3—C4—O4 | 134.6 (4) | Cl1—C14B—C15—C16 | 173.5 (6) |
C2—C3—C4—C3i | −50.5 (4) | C13—C14B—C15—C16 | 0.7 (11) |
C2—C11—C12—C13 | 178.7 (5) | C14A—C15—C16—C11 | 0.8 (10) |
C16—C11—C12—C13 | 2.3 (7) | C14B—C15—C16—C11 | 0.8 (10) |
Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1/2, −y, z−1/2; (iii) −x+1/2, −y, z+1/2; (iv) x−1/2, −y+1/2, −z+1/2; (v) x−1/2, −y+1/2, −z+3/2; (vi) x−1/2, y, −z+1/2; (vii) x−1/2, y, −z+3/2; (viii) x, y, z−1; (ix) x, −y+1/2, z−1; (x) x, −y+1/2, z+1; (xi) x+1/2, y, −z+3/2; (xii) x+1/2, −y+1/2, −z+1/2; (xiii) x+1/2, −y+1/2, −z+3/2; (xiv) x, y, z+1; (xv) x+1/2, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1xiv | 0.98 | 2.43 | 3.232 (4) | 138 |
C15—H15···Cl1ii | 0.93 | 2.82 | 3.745 (9) | 170 |
Symmetry codes: (ii) −x+1/2, −y, z−1/2; (xiv) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H15ClO2S |
Mr | 318.81 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 296 |
a, b, c (Å) | 11.5195 (5), 25.7589 (12), 5.2248 (2) |
V (Å3) | 1550.35 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.58 × 0.35 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.809, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 33450, 1954, 1551 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.211, 1.20 |
No. of reflections | 1954 |
No. of parameters | 106 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.42 |
Computer programs: APEX2 (Bruker, 2004), SAINT-NT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.98 | 2.43 | 3.232 (4) | 138 |
C15—H15···Cl1ii | 0.93 | 2.82 | 3.745 (9) | 170 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1/2, −y, z−1/2. |
Increasing interest has been focused on the stereochemical aspects of sulphoxides. The conformational analysis of cyclic sulphoxides is an area of attraction for many groups (Okada & Tanaka, 2002; Hutton et al., 2002; Contreras et al., 1998). Significant attention was earlier directed toward the conformational analysis of substituted thian-1-oxides (Freeman et al., 2001; Nagao et al., 1995). The conformational integrity of the sulphoxide has also generated interest in the various conditions under which it may undergo stereoisomerization. A large number of aliphatic, aromatic and cyclic sulphoxides exhibit antimicrobial activity (Ingold et al., 1999; Ansel et al., 2006; Rouvier et al., 2004). Although extensive studies on sulphoxides have disclosed their chemical and physico-chemical properties, little is known about the properties of the sulphinyl groups in cyclic sulphoxides. To investigate the conformations, substitution effect and antimicrobial activity of unsymmetrical thiopyran-4-one 1-oxides, the title compound was synthesized.
Thiruvalluvar et al., (2007) have reported a crystal structure of 2-(4-Fluorophenyl)-6-phenyltetrahydro-2H-thiopyran-4-one 1-oxide, wherein the thiopyran unit is in chair form. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The thiopyran unit of the title molecule, C17H15ClO2S, is in the chair form. The geometry around S1 atom is tetrahedral and C4 is planar. A crystallographic mirror plane bisects the molecule, passing through the O=S and the opposite C=O atoms of the central ring. The (p-chloro)phenyl at the 2 position and the phenyl ring at the 6 position have equatorial orientations. C2—H2···O1(x, y, 1 + z) and C15—H15···Cl1(1/2 - x, -y, -1/2 + z) intermolecular hydrogen bonds forming an infinite one dimensional chain with base vector [0 0 1] are found in the crystal structure. Further, a short intermolecular O1···C4(x, y, -1 + z) contact of 2.970 (5)Å is also found in the crystal structure.