Literature DB >> 22219888

2-(4-Methyl-phen-yl)-1-(phenyl-sulfon-yl)propan-2-ol.

Bao-Jun Shi, Liang-Zhu Huang, You-Qiang Li, Chang-Mei Si, Zhen-Ting Du.   

Abstract

The title compound, C(16)H(18)O(3)S, features a U-shape mol-ecular structure with a dihedral angle between the terminal benzene rings of 20.8 (1)°. An intra-molecular O-H⋯O hydrogen bond helps to stabilize the mol-ecular structure. Inter-molecular classical O-H⋯O and weak C-H⋯O hydrogen bonding is present in the crystal structure.

Entities:  

Year:  2011        PMID： 22219888      PMCID： PMC3247583          DOI： 10.1107/S1600536811039894

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the use of organic sulfones as inter­mediates in organic synthesis, see: Consiglio et al. (1983 ▶); Wenkert et al. (1983 ▶); Trost (1991 ▶). For related structures, see: Gu et al. (2004 ▶); Garst et al. (2006 ▶); Ding et al., (2009 ▶); Groszek et al. (2006 ▶); Shi et al. (2011 ▶). For background to our program to synthesis new herbicide derivatives, see: Du et al. (2011 ▶).

Experimental

Crystal data

C16H18O3S M = 290.36 Orthorhombic, a = 15.6696 (14) Å b = 11.7501 (11) Å c = 15.9042 (16) Å V = 2928.3 (5) Å3 Z = 8 Mo Kα radiation μ = 0.23 mm−1 T = 298 K 0.38 × 0.29 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.919, T max = 0.954 13679 measured reflections 2578 independent reflections 1590 reflections with I > 2σ(I) R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.141 S = 1.08 2578 reflections 183 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.30 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039894/xu5336sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039894/xu5336Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811039894/xu5336Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H18O3SDx = 1.317 Mg m−3
Mr = 290.36Melting point: 392 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2803 reflections
a = 15.6696 (14) Åθ = 2.5–23.6°
b = 11.7501 (11) ŵ = 0.23 mm−1
c = 15.9042 (16) ÅT = 298 K
V = 2928.3 (5) Å3Block, colorless
Z = 80.38 × 0.29 × 0.21 mm
F(000) = 1232
Bruker SMART 1000 CCD area-detector diffractometer2578 independent reflections
Radiation source: fine-focus sealed tube1590 reflections with I > 2σ(I)
graphiteRint = 0.055
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.919, Tmax = 0.954k = −7→13
13679 measured reflectionsl = −18→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.054P)2 + 2.2452P] where P = (Fo2 + 2Fc2)/3
2578 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
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.
xyzUiso*/Ueq
O10.16491 (15)0.5125 (2)0.51682 (13)0.0541 (7)
H10.11350.50150.51180.081*
O20.05450 (17)0.2052 (2)0.41610 (15)0.0608 (7)
O30.01924 (14)0.4061 (2)0.44403 (15)0.0607 (7)
S10.07045 (5)0.32361 (7)0.40083 (5)0.0424 (3)
C10.17920 (19)0.3470 (3)0.4275 (2)0.0441 (8)
H1A0.19180.30220.47720.053*
H1B0.21400.31710.38220.053*
C20.2081 (2)0.4699 (3)0.44465 (19)0.0428 (8)
C30.19648 (19)0.5463 (3)0.36837 (19)0.0376 (7)
C40.2366 (2)0.5198 (3)0.2928 (2)0.0446 (8)
H40.26910.45370.28920.053*
C50.2294 (2)0.5888 (3)0.2233 (2)0.0473 (9)
H50.25640.56800.17350.057*
C60.1827 (2)0.6890 (3)0.2262 (2)0.0453 (8)
C70.1425 (2)0.7151 (3)0.3009 (2)0.0477 (9)
H70.11010.78120.30430.057*
C80.1492 (2)0.6455 (3)0.3710 (2)0.0448 (8)
H80.12150.66590.42050.054*
C90.3024 (2)0.4680 (3)0.4693 (2)0.0586 (10)
H9A0.32110.54400.48150.088*
H9B0.33540.43750.42380.088*
H9C0.30970.42120.51830.088*
C100.1751 (3)0.7661 (3)0.1507 (2)0.0644 (11)
H10A0.15550.83970.16840.097*
H10B0.13520.73410.11150.097*
H10C0.22990.77350.12430.097*
C110.06017 (19)0.3471 (3)0.2917 (2)0.0402 (8)
C120.0856 (2)0.2625 (3)0.2375 (2)0.0557 (10)
H120.10850.19500.25810.067*
C130.0767 (3)0.2792 (4)0.1524 (3)0.0721 (13)
H130.09350.22240.11510.086*
C140.0435 (3)0.3785 (5)0.1222 (3)0.0742 (13)
H140.03780.38890.06450.089*
C150.0186 (3)0.4630 (4)0.1765 (3)0.0698 (12)
H15−0.00360.53070.15550.084*
C160.0264 (2)0.4476 (3)0.2624 (2)0.0546 (9)
H160.00920.50420.29960.065*
U11U22U33U12U13U23
O10.0580 (15)0.0663 (17)0.0380 (13)−0.0058 (13)0.0003 (11)−0.0134 (12)
O20.0805 (18)0.0463 (15)0.0555 (15)−0.0190 (13)−0.0042 (13)0.0066 (12)
O30.0468 (14)0.0772 (18)0.0582 (15)0.0029 (13)0.0069 (12)−0.0265 (14)
S10.0442 (5)0.0438 (5)0.0392 (5)−0.0035 (4)0.0028 (4)−0.0042 (4)
C10.0426 (19)0.049 (2)0.0409 (18)0.0050 (16)0.0008 (15)0.0056 (16)
C20.0438 (19)0.046 (2)0.0384 (18)−0.0014 (16)0.0013 (14)−0.0037 (16)
C30.0355 (17)0.0355 (18)0.0417 (18)−0.0049 (14)−0.0042 (14)−0.0056 (15)
C40.0432 (19)0.042 (2)0.0488 (19)0.0049 (16)0.0036 (15)−0.0011 (17)
C50.048 (2)0.049 (2)0.045 (2)−0.0008 (17)0.0041 (16)0.0005 (17)
C60.0387 (18)0.046 (2)0.051 (2)−0.0055 (16)−0.0084 (16)0.0015 (17)
C70.0421 (19)0.039 (2)0.062 (2)0.0009 (16)−0.0043 (17)−0.0049 (18)
C80.0430 (18)0.044 (2)0.047 (2)−0.0028 (17)0.0003 (15)−0.0084 (17)
C90.048 (2)0.071 (3)0.057 (2)−0.0061 (19)−0.0154 (17)0.007 (2)
C100.067 (3)0.066 (3)0.060 (2)0.002 (2)−0.006 (2)0.012 (2)
C110.0367 (17)0.042 (2)0.0421 (18)−0.0008 (15)−0.0010 (14)0.0012 (15)
C120.057 (2)0.063 (2)0.047 (2)0.0100 (19)0.0081 (18)−0.0064 (19)
C130.063 (3)0.106 (4)0.048 (2)0.003 (3)0.011 (2)−0.016 (3)
C140.064 (3)0.110 (4)0.048 (2)−0.021 (3)−0.002 (2)0.020 (3)
C150.065 (3)0.068 (3)0.077 (3)−0.020 (2)−0.025 (2)0.030 (3)
C160.052 (2)0.044 (2)0.068 (3)−0.0073 (18)−0.0150 (19)0.0010 (19)
O1—C21.424 (4)C7—H70.9300
O1—H10.8200C8—H80.9300
O2—S11.435 (2)C9—H9A0.9600
O3—S11.433 (2)C9—H9B0.9600
S1—C111.764 (3)C9—H9C0.9600
S1—C11.778 (3)C10—H10A0.9600
C1—C21.538 (4)C10—H10B0.9600
C1—H1A0.9700C10—H10C0.9600
C1—H1B0.9700C11—C121.375 (5)
C2—C31.520 (4)C11—C161.376 (5)
C2—C91.528 (4)C12—C131.375 (5)
C3—C81.382 (4)C12—H120.9300
C3—C41.392 (4)C13—C141.365 (6)
C4—C51.375 (4)C13—H130.9300
C4—H40.9300C14—C151.373 (6)
C5—C61.387 (5)C14—H140.9300
C5—H50.9300C15—C161.384 (5)
C6—C71.378 (5)C15—H150.9300
C6—C101.509 (5)C16—H160.9300
C7—C81.387 (5)
C2—O1—H1109.5C3—C8—C7120.9 (3)
O3—S1—O2118.50 (16)C3—C8—H8119.5
O3—S1—C11108.34 (15)C7—C8—H8119.5
O2—S1—C11107.58 (15)C2—C9—H9A109.5
O3—S1—C1108.52 (15)C2—C9—H9B109.5
O2—S1—C1106.05 (15)H9A—C9—H9B109.5
C11—S1—C1107.35 (15)C2—C9—H9C109.5
C2—C1—S1118.0 (2)H9A—C9—H9C109.5
C2—C1—H1A107.8H9B—C9—H9C109.5
S1—C1—H1A107.8C6—C10—H10A109.5
C2—C1—H1B107.8C6—C10—H10B109.5
S1—C1—H1B107.8H10A—C10—H10B109.5
H1A—C1—H1B107.1C6—C10—H10C109.5
O1—C2—C3112.3 (3)H10A—C10—H10C109.5
O1—C2—C9104.9 (3)H10B—C10—H10C109.5
C3—C2—C9109.2 (3)C12—C11—C16121.3 (3)
O1—C2—C1109.5 (3)C12—C11—S1118.5 (3)
C3—C2—C1112.2 (3)C16—C11—S1120.2 (3)
C9—C2—C1108.4 (3)C11—C12—C13119.0 (4)
C8—C3—C4117.2 (3)C11—C12—H12120.5
C8—C3—C2122.6 (3)C13—C12—H12120.5
C4—C3—C2120.2 (3)C14—C13—C12120.5 (4)
C5—C4—C3121.6 (3)C14—C13—H13119.8
C5—C4—H4119.2C12—C13—H13119.8
C3—C4—H4119.2C13—C14—C15120.3 (4)
C4—C5—C6121.1 (3)C13—C14—H14119.8
C4—C5—H5119.4C15—C14—H14119.8
C6—C5—H5119.4C14—C15—C16120.1 (4)
C7—C6—C5117.3 (3)C14—C15—H15119.9
C7—C6—C10121.1 (3)C16—C15—H15119.9
C5—C6—C10121.6 (3)C11—C16—C15118.7 (4)
C6—C7—C8121.8 (3)C11—C16—H16120.6
C6—C7—H7119.1C15—C16—H16120.6
C8—C7—H7119.1
O3—S1—C1—C2−32.7 (3)C10—C6—C7—C8−179.6 (3)
O2—S1—C1—C2−161.1 (2)C4—C3—C8—C70.0 (5)
C11—S1—C1—C284.2 (3)C2—C3—C8—C7177.7 (3)
S1—C1—C2—O164.0 (3)C6—C7—C8—C3−0.3 (5)
S1—C1—C2—C3−61.4 (3)O3—S1—C11—C12−163.9 (3)
S1—C1—C2—C9177.9 (2)O2—S1—C11—C12−34.7 (3)
O1—C2—C3—C80.2 (4)C1—S1—C11—C1279.1 (3)
C9—C2—C3—C8−115.7 (3)O3—S1—C11—C1615.4 (3)
C1—C2—C3—C8124.0 (3)O2—S1—C11—C16144.6 (3)
O1—C2—C3—C4177.9 (3)C1—S1—C11—C16−101.7 (3)
C9—C2—C3—C461.9 (4)C16—C11—C12—C13−0.2 (5)
C1—C2—C3—C4−58.3 (4)S1—C11—C12—C13179.0 (3)
C8—C3—C4—C5−0.3 (5)C11—C12—C13—C140.3 (6)
C2—C3—C4—C5−178.1 (3)C12—C13—C14—C150.0 (6)
C3—C4—C5—C61.0 (5)C13—C14—C15—C16−0.5 (6)
C4—C5—C6—C7−1.2 (5)C12—C11—C16—C15−0.2 (5)
C4—C5—C6—C10179.3 (3)S1—C11—C16—C15−179.5 (3)
C5—C6—C7—C80.9 (5)C14—C15—C16—C110.6 (6)
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.822.142.848 (3)144
O1—H1···O3i0.822.453.103 (3)137
C15—H15···O2ii0.932.483.403 (5)173
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O30.822.142.848 (3)144
O1—H1⋯O3i0.822.453.103 (3)137
C15—H15⋯O2ii0.932.483.403 (5)173

Symmetry codes: (i) ; (ii) .

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