organic compounds
rac-3-[(3-Chloroanilino)(4-chlorophenyl)methyl]thian-4-one
aFachbereich Chemie, Philipps Universität Marburg, Hans Meerwein Str., Marburg D-35032, Germany, and bDepartment of Organic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14335-186, Tehran, Iran
*Correspondence e-mail: harms@chemie.uni-marburg.de
In the title compound, C18H17Cl2NOS, the thiopyranone ring adopts a chair conformation, with the substituent in the axial position. The dihedral angle between the two benzene rings is 89.43 (1)°. In the crystal, molecules form inversion dimers through intermolecular N—H⋯O hydrogen bonds [graph set R22(8)].
Related literature
For the preparation and spectroscopic characterization of a series of related compounds and the p-tolyl)methly]dihydro-2H-thiopyran-4(3H)-one, see: Abaee et al. (2012). For the crystal structures of related compounds, see: Guo et al. (2007); Fun et al. (2009); Harms et al. (2012). For patterns in hydrogen bonding, see: Bernstein et al. (1995). For defining the of see: IUPAC (2012).
of 3-[(phenylamino)(Experimental
Crystal data
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Refinement
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Data collection: EXPOSE (Stoe & Cie, 1994); cell CELL (Stoe & Cie, 1994); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812004680/zs2176sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812004680/zs2176Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812004680/zs2176Isup3.cml
The title compound was synthesized using an anti-selective three-component Mannich reaction involving the thiopyran-4-one system (Abaee et al., 2012). Colourless crystals suitable for the
determination were grown from ethyl acetate.All C-bonded H atoms were placed in geometrical positions and constrained to ride on their parent atoms with C—H distances in the range 0.95–1.00 Å. The Uiso values were constrained to be 1.2Ueq of the parent C atom. The position of the N-bonded H atom has been refined freely with an isotropic displacement parameter. The N—H bond length is 0.81 (2) Å.
Data collection: EXPOSE (Stoe & Cie, 1994); cell
CELL (Stoe & Cie, 1994); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).C18H17Cl2NOS | F(000) = 760 |
Mr = 366.29 | Dx = 1.428 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8000 reflections |
a = 11.2611 (8) Å | θ = 1.9–25° |
b = 8.6686 (7) Å | µ = 0.51 mm−1 |
c = 18.0976 (12) Å | T = 193 K |
β = 105.266 (8)° | Plate, colourless |
V = 1704.3 (2) Å3 | 0.29 × 0.24 × 0.05 mm |
Z = 4 |
Stoe IPDS-1 image-plate diffractometer | 3134 independent reflections |
Radiation source: fine-focus sealed tube | 1867 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.4°, θmin = 1.9° |
ω scans | h = −13→13 |
Absorption correction: integration X-RED32 (Stoe & Cie, 2006) | k = −10→10 |
Tmin = 0.890, Tmax = 0.978 | l = −21→21 |
15404 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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.64 | w = 1/[σ2(Fo2) + (0.0127P)2] where P = (Fo2 + 2Fc2)/3 |
3134 reflections | (Δ/σ)max = 0.001 |
212 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C18H17Cl2NOS | V = 1704.3 (2) Å3 |
Mr = 366.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2611 (8) Å | µ = 0.51 mm−1 |
b = 8.6686 (7) Å | T = 193 K |
c = 18.0976 (12) Å | 0.29 × 0.24 × 0.05 mm |
β = 105.266 (8)° |
Stoe IPDS-1 image-plate diffractometer | 3134 independent reflections |
Absorption correction: integration X-RED32 (Stoe & Cie, 2006) | 1867 reflections with I > 2σ(I) |
Tmin = 0.890, Tmax = 0.978 | Rint = 0.042 |
15404 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.64 | Δρmax = 0.17 e Å−3 |
3134 reflections | Δρmin = −0.15 e Å−3 |
212 parameters |
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. |
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. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.31042 (19) | 0.2357 (2) | 0.53806 (11) | 0.0272 (5) | |
H2A | 0.3860 | 0.2956 | 0.5399 | 0.033* | |
H2B | 0.2797 | 0.1939 | 0.4856 | 0.033* | |
C3 | 0.21227 (18) | 0.3451 (2) | 0.55471 (10) | 0.0238 (5) | |
H3 | 0.1946 | 0.4265 | 0.5141 | 0.029* | |
C4 | 0.09371 (19) | 0.2559 (2) | 0.54853 (11) | 0.0260 (5) | |
C5 | 0.10024 (19) | 0.1153 (2) | 0.59821 (11) | 0.0282 (5) | |
H5A | 0.0184 | 0.0653 | 0.5864 | 0.034* | |
H5B | 0.1218 | 0.1472 | 0.6527 | 0.034* | |
C6 | 0.19574 (19) | −0.0013 (2) | 0.58604 (12) | 0.0308 (5) | |
H6A | 0.1703 | −0.0387 | 0.5325 | 0.037* | |
H6B | 0.1970 | −0.0910 | 0.6201 | 0.037* | |
C7 | 0.25464 (16) | 0.4273 (2) | 0.63362 (10) | 0.0213 (4) | |
H7 | 0.2599 | 0.3478 | 0.6744 | 0.026* | |
C9 | 0.15786 (17) | 0.6196 (2) | 0.70276 (11) | 0.0221 (4) | |
C10 | 0.23976 (18) | 0.5889 (2) | 0.77388 (11) | 0.0251 (4) | |
H10 | 0.3020 | 0.5129 | 0.7783 | 0.030* | |
C11 | 0.2297 (2) | 0.6703 (2) | 0.83810 (11) | 0.0288 (5) | |
C12 | 0.1428 (2) | 0.7834 (3) | 0.83454 (13) | 0.0365 (6) | |
H12 | 0.1373 | 0.8374 | 0.8792 | 0.044* | |
C13 | 0.06325 (19) | 0.8161 (3) | 0.76353 (13) | 0.0353 (5) | |
H13 | 0.0032 | 0.8948 | 0.7594 | 0.042* | |
C14 | 0.07008 (18) | 0.7357 (2) | 0.69860 (12) | 0.0277 (5) | |
H14 | 0.0145 | 0.7598 | 0.6507 | 0.033* | |
C15 | 0.38184 (17) | 0.4989 (2) | 0.64544 (10) | 0.0215 (4) | |
C16 | 0.48456 (17) | 0.4248 (2) | 0.69185 (10) | 0.0240 (4) | |
H16 | 0.4738 | 0.3333 | 0.7182 | 0.029* | |
C17 | 0.60194 (19) | 0.4826 (2) | 0.70002 (11) | 0.0266 (5) | |
H17 | 0.6714 | 0.4305 | 0.7312 | 0.032* | |
C18 | 0.61680 (18) | 0.6159 (2) | 0.66259 (10) | 0.0242 (4) | |
C19 | 0.51657 (18) | 0.6941 (2) | 0.61697 (11) | 0.0278 (5) | |
H19 | 0.5278 | 0.7872 | 0.5919 | 0.033* | |
C20 | 0.39949 (18) | 0.6339 (2) | 0.60864 (11) | 0.0266 (5) | |
H20 | 0.3303 | 0.6861 | 0.5772 | 0.032* | |
N8 | 0.15854 (16) | 0.5356 (2) | 0.63804 (10) | 0.0260 (4) | |
O1 | −0.00210 (14) | 0.29351 (18) | 0.50276 (9) | 0.0404 (4) | |
S1 | 0.34870 (5) | 0.07723 (6) | 0.60476 (3) | 0.02864 (13) | |
Cl1 | 0.33192 (6) | 0.62648 (7) | 0.92643 (3) | 0.04561 (17) | |
Cl2 | 0.76515 (5) | 0.68900 (7) | 0.67408 (3) | 0.03580 (14) | |
H8 | 0.1180 (19) | 0.569 (2) | 0.5974 (11) | 0.027 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0317 (12) | 0.0281 (12) | 0.0222 (10) | −0.0019 (10) | 0.0076 (9) | −0.0037 (9) |
C3 | 0.0298 (11) | 0.0228 (11) | 0.0172 (10) | 0.0003 (9) | 0.0031 (9) | 0.0016 (8) |
C4 | 0.0279 (12) | 0.0285 (12) | 0.0185 (10) | 0.0027 (9) | 0.0009 (9) | −0.0070 (9) |
C5 | 0.0262 (11) | 0.0277 (12) | 0.0297 (11) | −0.0043 (10) | 0.0058 (9) | 0.0001 (10) |
C6 | 0.0331 (12) | 0.0244 (11) | 0.0335 (12) | −0.0026 (10) | 0.0061 (10) | −0.0013 (10) |
C7 | 0.0233 (10) | 0.0211 (10) | 0.0184 (9) | 0.0029 (9) | 0.0035 (8) | 0.0015 (9) |
C9 | 0.0196 (10) | 0.0201 (11) | 0.0283 (10) | −0.0057 (9) | 0.0095 (9) | −0.0017 (9) |
C10 | 0.0255 (11) | 0.0216 (11) | 0.0307 (11) | −0.0034 (9) | 0.0116 (9) | −0.0013 (9) |
C11 | 0.0309 (12) | 0.0298 (13) | 0.0284 (11) | −0.0103 (10) | 0.0125 (10) | −0.0022 (10) |
C12 | 0.0368 (13) | 0.0357 (14) | 0.0444 (14) | −0.0102 (11) | 0.0239 (11) | −0.0131 (11) |
C13 | 0.0263 (12) | 0.0308 (13) | 0.0533 (14) | 0.0015 (11) | 0.0186 (11) | −0.0070 (11) |
C14 | 0.0209 (11) | 0.0262 (12) | 0.0369 (12) | −0.0015 (9) | 0.0095 (9) | 0.0000 (10) |
C15 | 0.0255 (11) | 0.0220 (10) | 0.0166 (10) | 0.0021 (9) | 0.0045 (8) | −0.0024 (9) |
C16 | 0.0281 (11) | 0.0220 (11) | 0.0199 (9) | 0.0000 (10) | 0.0026 (8) | 0.0017 (9) |
C17 | 0.0262 (11) | 0.0270 (12) | 0.0243 (10) | 0.0033 (10) | 0.0026 (9) | −0.0021 (9) |
C18 | 0.0241 (11) | 0.0244 (11) | 0.0245 (10) | −0.0013 (9) | 0.0072 (8) | −0.0060 (9) |
C19 | 0.0314 (12) | 0.0210 (11) | 0.0319 (11) | 0.0001 (10) | 0.0101 (10) | 0.0048 (10) |
C20 | 0.0240 (11) | 0.0234 (11) | 0.0312 (11) | 0.0061 (9) | 0.0053 (9) | 0.0052 (10) |
N8 | 0.0254 (10) | 0.0282 (11) | 0.0222 (9) | 0.0053 (8) | 0.0025 (8) | −0.0009 (8) |
O1 | 0.0317 (8) | 0.0408 (9) | 0.0384 (8) | 0.0017 (8) | −0.0090 (7) | 0.0025 (8) |
S1 | 0.0268 (3) | 0.0258 (3) | 0.0316 (3) | 0.0030 (3) | 0.0046 (2) | 0.0003 (2) |
Cl1 | 0.0576 (4) | 0.0523 (4) | 0.0252 (3) | −0.0036 (3) | 0.0077 (3) | −0.0042 (3) |
Cl2 | 0.0269 (3) | 0.0373 (3) | 0.0424 (3) | −0.0062 (3) | 0.0076 (2) | −0.0012 (3) |
C2—C3 | 1.545 (3) | C10—C11 | 1.389 (3) |
C2—S1 | 1.804 (2) | C10—H10 | 0.9500 |
C2—H2A | 0.9900 | C11—C12 | 1.375 (3) |
C2—H2B | 0.9900 | C11—Cl1 | 1.748 (2) |
C3—C4 | 1.521 (3) | C12—C13 | 1.388 (3) |
C3—C7 | 1.555 (2) | C12—H12 | 0.9500 |
C3—H3 | 1.0000 | C13—C14 | 1.385 (3) |
C4—O1 | 1.219 (2) | C13—H13 | 0.9500 |
C4—C5 | 1.505 (3) | C14—H14 | 0.9500 |
C5—C6 | 1.533 (3) | C15—C20 | 1.386 (3) |
C5—H5A | 0.9900 | C15—C16 | 1.395 (3) |
C5—H5B | 0.9900 | C16—C17 | 1.385 (3) |
C6—S1 | 1.799 (2) | C16—H16 | 0.9500 |
C6—H6A | 0.9900 | C17—C18 | 1.372 (3) |
C6—H6B | 0.9900 | C17—H17 | 0.9500 |
C7—N8 | 1.451 (2) | C18—C19 | 1.388 (3) |
C7—C15 | 1.524 (3) | C18—Cl2 | 1.747 (2) |
C7—H7 | 1.0000 | C19—C20 | 1.389 (3) |
C9—N8 | 1.381 (2) | C19—H19 | 0.9500 |
C9—C10 | 1.397 (3) | C20—H20 | 0.9500 |
C9—C14 | 1.399 (3) | N8—H8 | 0.81 (2) |
C3—C2—S1 | 113.20 (13) | C11—C10—H10 | 120.2 |
C3—C2—H2A | 108.9 | C9—C10—H10 | 120.2 |
S1—C2—H2A | 108.9 | C12—C11—C10 | 122.5 (2) |
C3—C2—H2B | 108.9 | C12—C11—Cl1 | 119.15 (16) |
S1—C2—H2B | 108.9 | C10—C11—Cl1 | 118.39 (17) |
H2A—C2—H2B | 107.8 | C11—C12—C13 | 117.82 (19) |
C4—C3—C2 | 109.45 (16) | C11—C12—H12 | 121.1 |
C4—C3—C7 | 110.60 (15) | C13—C12—H12 | 121.1 |
C2—C3—C7 | 113.47 (15) | C14—C13—C12 | 121.1 (2) |
C4—C3—H3 | 107.7 | C14—C13—H13 | 119.5 |
C2—C3—H3 | 107.7 | C12—C13—H13 | 119.5 |
C7—C3—H3 | 107.7 | C13—C14—C9 | 120.82 (19) |
O1—C4—C5 | 121.19 (19) | C13—C14—H14 | 119.6 |
O1—C4—C3 | 121.12 (19) | C9—C14—H14 | 119.6 |
C5—C4—C3 | 117.63 (17) | C20—C15—C16 | 118.50 (18) |
C4—C5—C6 | 111.94 (16) | C20—C15—C7 | 121.65 (17) |
C4—C5—H5A | 109.2 | C16—C15—C7 | 119.80 (17) |
C6—C5—H5A | 109.2 | C17—C16—C15 | 120.98 (19) |
C4—C5—H5B | 109.2 | C17—C16—H16 | 119.5 |
C6—C5—H5B | 109.2 | C15—C16—H16 | 119.5 |
H5A—C5—H5B | 107.9 | C18—C17—C16 | 119.29 (19) |
C5—C6—S1 | 113.37 (15) | C18—C17—H17 | 120.4 |
C5—C6—H6A | 108.9 | C16—C17—H17 | 120.4 |
S1—C6—H6A | 108.9 | C17—C18—C19 | 121.32 (19) |
C5—C6—H6B | 108.9 | C17—C18—Cl2 | 118.95 (16) |
S1—C6—H6B | 108.9 | C19—C18—Cl2 | 119.73 (16) |
H6A—C6—H6B | 107.7 | C18—C19—C20 | 118.74 (19) |
N8—C7—C15 | 114.59 (17) | C18—C19—H19 | 120.6 |
N8—C7—C3 | 107.13 (14) | C20—C19—H19 | 120.6 |
C15—C7—C3 | 111.44 (14) | C15—C20—C19 | 121.15 (19) |
N8—C7—H7 | 107.8 | C15—C20—H20 | 119.4 |
C15—C7—H7 | 107.8 | C19—C20—H20 | 119.4 |
C3—C7—H7 | 107.8 | C9—N8—C7 | 123.97 (17) |
N8—C9—C10 | 122.09 (18) | C9—N8—H8 | 116.9 (15) |
N8—C9—C14 | 119.70 (18) | C7—N8—H8 | 115.6 (14) |
C10—C9—C14 | 118.17 (18) | C6—S1—C2 | 96.53 (10) |
C11—C10—C9 | 119.63 (19) | ||
S1—C2—C3—C4 | −61.14 (18) | C10—C9—C14—C13 | −1.2 (3) |
S1—C2—C3—C7 | 62.93 (19) | N8—C7—C15—C20 | −46.3 (2) |
C2—C3—C4—O1 | −120.6 (2) | C3—C7—C15—C20 | 75.5 (2) |
C7—C3—C4—O1 | 113.7 (2) | N8—C7—C15—C16 | 136.32 (18) |
C2—C3—C4—C5 | 56.6 (2) | C3—C7—C15—C16 | −101.83 (19) |
C7—C3—C4—C5 | −69.1 (2) | C20—C15—C16—C17 | −1.2 (3) |
O1—C4—C5—C6 | 121.5 (2) | C7—C15—C16—C17 | 176.23 (17) |
C3—C4—C5—C6 | −55.7 (2) | C15—C16—C17—C18 | 0.8 (3) |
C4—C5—C6—S1 | 58.2 (2) | C16—C17—C18—C19 | 0.3 (3) |
C4—C3—C7—N8 | −61.7 (2) | C16—C17—C18—Cl2 | 179.32 (15) |
C2—C3—C7—N8 | 174.84 (16) | C17—C18—C19—C20 | −0.9 (3) |
C4—C3—C7—C15 | 172.20 (16) | Cl2—C18—C19—C20 | 180.00 (15) |
C2—C3—C7—C15 | 48.8 (2) | C16—C15—C20—C19 | 0.5 (3) |
N8—C9—C10—C11 | −175.75 (18) | C7—C15—C20—C19 | −176.88 (18) |
C14—C9—C10—C11 | 1.9 (3) | C18—C19—C20—C15 | 0.5 (3) |
C9—C10—C11—C12 | −1.3 (3) | C10—C9—N8—C7 | −10.8 (3) |
C9—C10—C11—Cl1 | 178.88 (15) | C14—C9—N8—C7 | 171.62 (18) |
C10—C11—C12—C13 | −0.2 (3) | C15—C7—N8—C9 | −62.2 (2) |
Cl1—C11—C12—C13 | 179.69 (16) | C3—C7—N8—C9 | 173.59 (17) |
C11—C12—C13—C14 | 0.9 (3) | C5—C6—S1—C2 | −56.47 (16) |
C12—C13—C14—C9 | −0.3 (3) | C3—C2—S1—C6 | 58.68 (16) |
N8—C9—C14—C13 | 176.54 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8···O1i | 0.81 (2) | 2.27 (2) | 3.070 (2) | 168 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H17Cl2NOS |
Mr | 366.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 193 |
a, b, c (Å) | 11.2611 (8), 8.6686 (7), 18.0976 (12) |
β (°) | 105.266 (8) |
V (Å3) | 1704.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.51 |
Crystal size (mm) | 0.29 × 0.24 × 0.05 |
Data collection | |
Diffractometer | Stoe IPDS1 image-plate diffractometer |
Absorption correction | Integration X-RED32 (Stoe & Cie, 2006) |
Tmin, Tmax | 0.890, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15404, 3134, 1867 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.604 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.048, 0.64 |
No. of reflections | 3134 |
No. of parameters | 212 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: EXPOSE (Stoe & Cie, 1994), CELL (Stoe & Cie, 1994), X-RED32 (Stoe & Cie, 2006), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), publCIF (Westrip, 2010), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8···O1i | 0.81 (2) | 2.27 (2) | 3.070 (2) | 168 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
References
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The title compound is an example of a product from an anti-selective three-component Mannich reaction involving the thiopyran-4-one system (Abaee et al., 2012). The same anti configuration has been found recently in the crystal structures of two other compounds of this series (Abaee et al., 2012; Harms et al., 2012). In the title compund the thiopyranone ring adopts a chair-like conformation with the substituent in the axial position. The relative configuration of the stereogenic centres at C3 and C7 is R*, S* (IUPAC, 1997). The dihedral angle between the two benzene rings in the molecule is 89.43 (10)°. In the crystal packing the molecules form discrete centrosymmetric dimers are through intermolecular N—H···O hydrogen bonds [graph set R22(8)] (Bernstein et al., 1995). For further details see Table 1 and Fig. 1.