organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-Meth­­oxy-4-methyl-1-[1-(phenyl­sulfon­yl)propan-2-yl]benzene

aState Key Laboratory of Crop Stress Biology for Arid Areas, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China, and bCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
*Correspondence e-mail: duzt@nwsuaf.edu.cn

(Received 27 August 2011; accepted 3 September 2011; online 14 September 2011)

The title mol­ecule, C17H20O3S, displays a U-shaped structure; the two benzene rings are nearly parallel and partially overlapped to each other, the dihedral angle and centroid-to-centroid distance being 15.0 (2)° and 3.723 (2) Å. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules, forming supra­molecular chains running along the a axis.

Related literature

For propargylic sulfides as precusors of indene derivatives, see: Peng et al. (2007[Peng, L., Zhang, X., Zhang, S. & Wang, J. (2007). J. Org. Chem. 72, 1192-1197.]). For a related structure, see: Xi et al. (2004[Xi, C., Lai, C., Chen, C. & Wang, R. (2004). Synlett, 9, 1595-1597.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20O3S

  • Mr = 304.39

  • Monoclinic, P 21 /c

  • a = 9.101 (1) Å

  • b = 12.2579 (14) Å

  • c = 15.9251 (17) Å

  • β = 118.307 (1)°

  • V = 1564.1 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 298 K

  • 0.42 × 0.27 × 0.13 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.915, Tmax = 0.973

  • 7654 measured reflections

  • 2754 independent reflections

  • 1641 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.187

  • S = 1.08

  • 2754 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C11—H11B⋯O2i 0.96 2.59 3.503 (6) 159
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Propargylic sulfides have been studied as the precusor of indene derivatives (Peng et al. 2007). As a result of our program of screening of new indene derivatives, we obtained a intermediate compound C17H20O3S (I) and the synthesis and structure are reported here.

There are two benzene rings in the title compound and they exhibit face-to-face conformation. The dihedral angle between the two benzene rings is 12.0 (2)°. The molecules of I are crystalized in P21/c space group which is different from that of 2–phenyl–1–(p–toluenesulfonyl)propan–2–ol (Pbca, Xi et al., 2004). In the crystal structure there is an intermolecular C—H···O hydrogen-bonding interaction (Table 1), which is helpful to the stabilization of the packing.

Related literature top

For propargylic sulfides as precusors of indene derivatives, see: Peng et al. (2007). For a related structure, see: Xi et al. (2004).

Experimental top

A mixture of 1-(1-bromopropan-2-yl)-4-methylbenzene (1.0 g, 4.7 mmol) and sodium benzenesulfinate (0.83 g, 5.6 mmol) in dry DMF (20 mL) was stirred over night at 80°C. When the reaction was completed, 50 mL water was added to the mixture and was extracted with ethyl acetate. The ethyl acetate layer was washed by 50 mL water, then 15 mL saturated sodium chloride and over anhydrous sodium sulfate and was separated on silica gel column chromatography with a gradient of petroleum ether and ethyl acetate as eluent to yield 1.3 g the title compound. The compound was then dissolved in ethyl acetate, and colorless crystals were formed on slow evaporation at room temperature over one week.

Refinement top

All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H = 0.93 Å and N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C, N).

Structure description top

Propargylic sulfides have been studied as the precusor of indene derivatives (Peng et al. 2007). As a result of our program of screening of new indene derivatives, we obtained a intermediate compound C17H20O3S (I) and the synthesis and structure are reported here.

There are two benzene rings in the title compound and they exhibit face-to-face conformation. The dihedral angle between the two benzene rings is 12.0 (2)°. The molecules of I are crystalized in P21/c space group which is different from that of 2–phenyl–1–(p–toluenesulfonyl)propan–2–ol (Pbca, Xi et al., 2004). In the crystal structure there is an intermolecular C—H···O hydrogen-bonding interaction (Table 1), which is helpful to the stabilization of the packing.

For propargylic sulfides as precusors of indene derivatives, see: Peng et al. (2007). For a related structure, see: Xi et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of (I) viewed along the a axis, with hydrogen bonds shown as dashed lines.
2-Methoxy-4-methyl-1-[1-(phenylsulfonyl)propan-2-yl]benzene top
Crystal data top
C17H20O3SF(000) = 648
Mr = 304.39Dx = 1.293 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1375 reflections
a = 9.101 (1) Åθ = 2.5–23.0°
b = 12.2579 (14) ŵ = 0.21 mm1
c = 15.9251 (17) ÅT = 298 K
β = 118.307 (1)°Block, colorless
V = 1564.1 (3) Å30.42 × 0.27 × 0.13 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2754 independent reflections
Radiation source: fine-focus sealed tube1641 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.915, Tmax = 0.973k = 1414
7654 measured reflectionsl = 1118
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0032P)2 + 0.4143P]
where P = (Fo2 + 2Fc2)/3
2754 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C17H20O3SV = 1564.1 (3) Å3
Mr = 304.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.101 (1) ŵ = 0.21 mm1
b = 12.2579 (14) ÅT = 298 K
c = 15.9251 (17) Å0.42 × 0.27 × 0.13 mm
β = 118.307 (1)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2754 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1641 reflections with I > 2σ(I)
Tmin = 0.915, Tmax = 0.973Rint = 0.050
7654 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.08Δρmax = 0.26 e Å3
2754 reflectionsΔρmin = 0.23 e Å3
193 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.9829 (3)0.3534 (2)0.33678 (17)0.0512 (7)
O20.3680 (3)0.4052 (2)0.16790 (19)0.0622 (8)
O30.4268 (4)0.2682 (2)0.2938 (2)0.0677 (9)
S10.48398 (11)0.33304 (8)0.23977 (7)0.0450 (3)
C10.6540 (4)0.4104 (3)0.3246 (2)0.0419 (9)
H1A0.62150.44150.36930.050*
H1B0.74600.36080.36010.050*
C20.7182 (4)0.5027 (3)0.2863 (3)0.0431 (9)
H20.62300.55080.24960.052*
C30.7823 (4)0.4663 (3)0.2192 (2)0.0372 (9)
C40.9128 (4)0.3909 (3)0.2449 (3)0.0394 (9)
C50.9644 (4)0.3587 (3)0.1804 (3)0.0434 (9)
H51.05170.30910.19930.052*
C60.8891 (4)0.3985 (3)0.0877 (3)0.0429 (9)
C70.7631 (4)0.4745 (3)0.0628 (3)0.0470 (10)
H70.71230.50400.00160.056*
C80.7120 (4)0.5070 (3)0.1277 (3)0.0453 (10)
H80.62700.55830.10910.054*
C90.8460 (5)0.5702 (3)0.3700 (3)0.0619 (12)
H9A0.94000.52530.40950.093*
H9B0.79550.59730.40690.093*
H9C0.88250.63050.34600.093*
C101.1077 (5)0.2713 (4)0.3645 (3)0.0709 (13)
H10A1.06220.20830.32460.106*
H10B1.14450.25140.42980.106*
H10C1.20050.29870.35790.106*
C110.9425 (5)0.3583 (4)0.0172 (3)0.0630 (12)
H11A0.90190.28540.00210.095*
H11B1.06210.35860.04630.095*
H11C0.89750.40530.03760.095*
C120.5631 (4)0.2425 (3)0.1847 (3)0.0381 (9)
C130.6598 (5)0.1548 (3)0.2355 (3)0.0529 (10)
H130.68510.14410.29870.063*
C140.7178 (6)0.0837 (3)0.1916 (4)0.0674 (13)
H140.78390.02480.22550.081*
C150.6790 (6)0.0988 (4)0.0979 (4)0.0694 (13)
H150.71830.04960.06870.083*
C160.5828 (5)0.1856 (4)0.0468 (3)0.0628 (12)
H160.55750.19580.01650.075*
C170.5239 (5)0.2579 (3)0.0910 (3)0.0481 (10)
H170.45780.31680.05720.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0449 (15)0.0676 (16)0.0393 (15)0.0191 (13)0.0185 (13)0.0142 (13)
O20.0437 (16)0.0711 (17)0.0598 (18)0.0197 (13)0.0147 (15)0.0003 (15)
O30.074 (2)0.0761 (18)0.077 (2)0.0205 (16)0.0555 (18)0.0102 (17)
S10.0406 (6)0.0526 (6)0.0480 (6)0.0027 (4)0.0259 (5)0.0040 (5)
C10.044 (2)0.0461 (19)0.039 (2)0.0018 (16)0.0228 (18)0.0041 (17)
C20.045 (2)0.0388 (19)0.047 (2)0.0029 (16)0.0223 (19)0.0027 (17)
C30.0347 (19)0.0327 (17)0.043 (2)0.0027 (15)0.0171 (18)0.0024 (16)
C40.036 (2)0.043 (2)0.037 (2)0.0035 (16)0.0158 (18)0.0027 (17)
C50.036 (2)0.045 (2)0.048 (2)0.0028 (16)0.0190 (19)0.0011 (18)
C60.040 (2)0.046 (2)0.044 (2)0.0085 (16)0.0200 (18)0.0016 (17)
C70.046 (2)0.054 (2)0.036 (2)0.0035 (18)0.0164 (19)0.0102 (18)
C80.042 (2)0.041 (2)0.051 (2)0.0014 (16)0.021 (2)0.0116 (18)
C90.069 (3)0.054 (2)0.065 (3)0.009 (2)0.034 (3)0.012 (2)
C100.058 (3)0.095 (3)0.063 (3)0.039 (2)0.032 (2)0.035 (3)
C110.067 (3)0.082 (3)0.046 (2)0.005 (2)0.031 (2)0.008 (2)
C120.035 (2)0.0393 (18)0.040 (2)0.0058 (15)0.0178 (17)0.0037 (17)
C130.054 (2)0.057 (2)0.049 (2)0.0062 (19)0.025 (2)0.008 (2)
C140.067 (3)0.047 (2)0.097 (4)0.013 (2)0.046 (3)0.007 (3)
C150.079 (3)0.058 (3)0.085 (4)0.000 (2)0.050 (3)0.017 (3)
C160.070 (3)0.072 (3)0.052 (3)0.004 (2)0.033 (2)0.012 (2)
C170.049 (2)0.051 (2)0.043 (2)0.0013 (18)0.021 (2)0.0019 (19)
Geometric parameters (Å, º) top
O1—C41.369 (4)C8—H80.9300
O1—C101.422 (4)C9—H9A0.9600
O2—S11.435 (3)C9—H9B0.9600
O3—S11.438 (3)C9—H9C0.9600
S1—C121.766 (4)C10—H10A0.9600
S1—C11.771 (3)C10—H10B0.9600
C1—C21.527 (5)C10—H10C0.9600
C1—H1A0.9700C11—H11A0.9600
C1—H1B0.9700C11—H11B0.9600
C2—C31.507 (5)C11—H11C0.9600
C2—C91.530 (5)C12—C171.372 (5)
C2—H20.9800C12—C131.382 (5)
C3—C81.378 (5)C13—C141.370 (6)
C3—C41.404 (5)C13—H130.9300
C4—C51.375 (5)C14—C151.374 (6)
C5—C61.389 (5)C14—H140.9300
C5—H50.9300C15—C161.373 (6)
C6—C71.382 (5)C15—H150.9300
C6—C111.501 (5)C16—C171.388 (5)
C7—C81.379 (5)C16—H160.9300
C7—H70.9300C17—H170.9300
C4—O1—C10117.9 (3)C2—C9—H9A109.5
O2—S1—O3118.67 (18)C2—C9—H9B109.5
O2—S1—C12108.05 (17)H9A—C9—H9B109.5
O3—S1—C12107.38 (16)C2—C9—H9C109.5
O2—S1—C1108.94 (16)H9A—C9—H9C109.5
O3—S1—C1105.84 (17)H9B—C9—H9C109.5
C12—S1—C1107.48 (17)O1—C10—H10A109.5
C2—C1—S1117.0 (2)O1—C10—H10B109.5
C2—C1—H1A108.0H10A—C10—H10B109.5
S1—C1—H1A108.0O1—C10—H10C109.5
C2—C1—H1B108.0H10A—C10—H10C109.5
S1—C1—H1B108.0H10B—C10—H10C109.5
H1A—C1—H1B107.3C6—C11—H11A109.5
C3—C2—C1114.4 (3)C6—C11—H11B109.5
C3—C2—C9112.8 (3)H11A—C11—H11B109.5
C1—C2—C9109.2 (3)C6—C11—H11C109.5
C3—C2—H2106.6H11A—C11—H11C109.5
C1—C2—H2106.6H11B—C11—H11C109.5
C9—C2—H2106.6C17—C12—C13120.6 (4)
C8—C3—C4116.8 (4)C17—C12—S1119.8 (3)
C8—C3—C2120.0 (3)C13—C12—S1119.6 (3)
C4—C3—C2123.2 (3)C14—C13—C12119.3 (4)
O1—C4—C5123.4 (3)C14—C13—H13120.4
O1—C4—C3115.7 (3)C12—C13—H13120.4
C5—C4—C3120.9 (3)C13—C14—C15120.4 (4)
C4—C5—C6121.5 (3)C13—C14—H14119.8
C4—C5—H5119.3C15—C14—H14119.8
C6—C5—H5119.3C16—C15—C14120.7 (4)
C7—C6—C5117.8 (4)C16—C15—H15119.6
C7—C6—C11121.7 (4)C14—C15—H15119.6
C5—C6—C11120.5 (3)C15—C16—C17119.1 (4)
C8—C7—C6120.6 (4)C15—C16—H16120.5
C8—C7—H7119.7C17—C16—H16120.5
C6—C7—H7119.7C12—C17—C16119.9 (4)
C3—C8—C7122.4 (3)C12—C17—H17120.0
C3—C8—H8118.8C16—C17—H17120.0
C7—C8—H8118.8
O2—S1—C1—C239.9 (3)C5—C6—C7—C81.6 (5)
O3—S1—C1—C2168.6 (3)C11—C6—C7—C8177.5 (3)
C12—S1—C1—C276.9 (3)C4—C3—C8—C71.4 (5)
S1—C1—C2—C360.9 (4)C2—C3—C8—C7178.4 (3)
S1—C1—C2—C9171.6 (3)C6—C7—C8—C30.1 (5)
C1—C2—C3—C8121.4 (3)O2—S1—C12—C177.0 (3)
C9—C2—C3—C8112.9 (4)O3—S1—C12—C17136.1 (3)
C1—C2—C3—C458.5 (4)C1—S1—C12—C17110.4 (3)
C9—C2—C3—C467.2 (4)O2—S1—C12—C13171.0 (3)
C10—O1—C4—C54.4 (5)O3—S1—C12—C1341.9 (3)
C10—O1—C4—C3175.7 (3)C1—S1—C12—C1371.6 (3)
C8—C3—C4—O1178.7 (3)C17—C12—C13—C140.7 (6)
C2—C3—C4—O11.4 (5)S1—C12—C13—C14178.7 (3)
C8—C3—C4—C51.2 (5)C12—C13—C14—C150.7 (6)
C2—C3—C4—C5178.7 (3)C13—C14—C15—C160.5 (7)
O1—C4—C5—C6179.6 (3)C14—C15—C16—C170.5 (7)
C3—C4—C5—C60.5 (5)C13—C12—C17—C160.7 (5)
C4—C5—C6—C71.9 (5)S1—C12—C17—C16178.6 (3)
C4—C5—C6—C11177.3 (3)C15—C16—C17—C120.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11B···O2i0.962.593.503 (6)159
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H20O3S
Mr304.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.101 (1), 12.2579 (14), 15.9251 (17)
β (°) 118.307 (1)
V3)1564.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.42 × 0.27 × 0.13
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.915, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
7654, 2754, 1641
Rint0.050
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.187, 1.08
No. of reflections2754
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.23

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11B···O2i0.962.593.503 (6)159
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

Financial support from the Fundamental Research Funds for the Central Universities in NWSUAF (QN2009048) and the Excellent Young Funds (211020712) is greatly appreciated.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationPeng, L., Zhang, X., Zhang, S. & Wang, J. (2007). J. Org. Chem. 72, 1192–1197.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXi, C., Lai, C., Chen, C. & Wang, R. (2004). Synlett, 9, 1595–1597.  Web of Science CSD CrossRef Google Scholar

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