Literature DB >> 21581061

Isopropyl 2-(4,6-dimethyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Hong Dae Choi, Pil Ja Seo, Byeng Wha Son, Uk Lee.   

Abstract

Mol-ecules of title compound, C(16)H(20)O(4)S, which was synthesized by the oxidation of isopropyl 2-(4,6-dimethyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate, inter-act through C-H⋯π inter-actions between a methyl-ene H atom and the aromatic carbon ring of the benzofuran ring system, and by C-H⋯O hydrogen bonds. Adjacent stacked mol-ecules exhibit a carbon-yl-carbonyl inter-action [3.295 (2) Å]. The O atom of the methyl-sulfinyl group is disordered over two positions with site-occupancy factors of 0.9 and 0.1.

Entities:  

Year:  2008        PMID： 21581061      PMCID： PMC2959738          DOI： 10.1107/S1600536808034466

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


Related literature

For the crystal structures of similar alkyl 2-(3-methyl­sulfinyl-1-benzofuran- 2-yl)acetate derivatives, see: Choi et al. (2007 ▶, 2008 ▶). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C16H20O4S M = 308.38 Triclinic, a = 6.308 (1) Å b = 11.340 (2) Å c = 11.506 (2) Å α = 81.403 (3)° β = 77.205 (3)° γ = 83.167 (4)° V = 790.4 (2) Å3 Z = 2 Mo Kα radiation μ = 0.22 mm−1 T = 298 (2) K 0.40 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: none 4195 measured reflections 2760 independent reflections 2270 reflections with I > 2σ(I) R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.126 S = 1.05 2760 reflections 202 parameters 7 restraints H-atom parameters constrained Δρmax = 0.40 e Å−3 Δρmin = −0.27 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034466/ng2503sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034466/ng2503Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H20O4SZ = 2
Mr = 308.38F(000) = 328
Triclinic, P1Dx = 1.296 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.308 (1) ÅCell parameters from 2459 reflections
b = 11.340 (2) Åθ = 2.4–28.0°
c = 11.506 (2) ŵ = 0.22 mm−1
α = 81.403 (3)°T = 298 K
β = 77.205 (3)°Block, colorless
γ = 83.167 (4)°0.40 × 0.30 × 0.10 mm
V = 790.4 (2) Å3
Bruker SMART CCD diffractometer2270 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
graphiteθmax = 25.0°, θmin = 2.4°
Detector resolution: 10.0 pixels mm-1h = −6→7
φ and ω scansk = −8→13
4195 measured reflectionsl = −13→13
2760 independent reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.126H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0676P)2 + 0.1659P] where P = (Fo2 + 2Fc2)/3
2760 reflections(Δ/σ)max < 0.001
202 parametersΔρmax = 0.40 e Å−3
7 restraintsΔρmin = −0.27 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*/UeqOcc. (<1)
S0.14112 (9)0.43525 (5)0.31658 (6)0.0639 (2)
O10.2743 (2)0.14311 (12)0.15511 (12)0.0528 (4)
O2−0.2895 (2)0.15214 (13)0.49041 (11)0.0503 (4)
O30.0716 (2)0.13761 (14)0.48320 (14)0.0612 (4)
O4A−0.0855 (3)0.41447 (18)0.37312 (18)0.0742 (5)0.90
O4B0.082 (3)0.5555 (7)0.2602 (15)0.086 (5)0.10
C10.2493 (3)0.31729 (18)0.22999 (17)0.0471 (5)
C20.4558 (3)0.30687 (18)0.14521 (17)0.0480 (5)
C30.6322 (3)0.3783 (2)0.10060 (19)0.0573 (5)
C40.8036 (4)0.3295 (3)0.0188 (2)0.0697 (7)
H40.92310.3739−0.01180.084*
C50.8091 (4)0.2190 (3)−0.0207 (2)0.0705 (7)
C60.6334 (3)0.1514 (2)0.0214 (2)0.0634 (6)
H60.63070.0778−0.00440.076*
C70.4621 (3)0.19809 (19)0.10351 (17)0.0504 (5)
C80.1482 (3)0.21824 (18)0.23284 (17)0.0478 (5)
C9−0.0638 (3)0.1747 (2)0.30051 (18)0.0538 (5)
H9A−0.08260.10050.27320.065*
H9B−0.18140.23300.28250.065*
C10−0.0808 (3)0.15375 (17)0.43450 (18)0.0461 (4)
C11−0.3372 (3)0.13159 (19)0.62208 (17)0.0523 (5)
H11−0.21260.08500.64980.063*
C12−0.3741 (5)0.2506 (2)0.6681 (2)0.0836 (8)
H12A−0.49510.29670.64020.100*
H12B−0.24550.29270.63930.100*
H12C−0.40550.23890.75430.100*
C13−0.5315 (4)0.0596 (2)0.6574 (2)0.0671 (6)
H13A−0.4967−0.01440.62340.080*
H13B−0.65240.10410.62800.080*
H13C−0.56990.04300.74340.080*
C140.6363 (4)0.4994 (2)0.1375 (2)0.0748 (7)
H14A0.70170.49080.20650.112*
H14B0.48980.53600.15710.112*
H14C0.71990.54880.07250.112*
C151.0074 (4)0.1738 (4)−0.1096 (3)0.1018 (11)
H15A0.98170.0989−0.13110.153*
H15B1.13290.1626−0.07350.153*
H15C1.03270.2313−0.18040.153*
C160.3028 (4)0.3962 (2)0.4279 (2)0.0661 (6)
H16A0.26270.45150.48630.099*
H16B0.45430.39960.39050.099*
H16C0.27840.31660.46690.099*
U11U22U33U12U13U23
S0.0584 (4)0.0639 (4)0.0712 (4)0.0072 (3)−0.0154 (3)−0.0215 (3)
O10.0453 (8)0.0637 (9)0.0494 (8)−0.0128 (6)0.0000 (6)−0.0156 (6)
O20.0364 (7)0.0699 (9)0.0424 (7)−0.0089 (6)−0.0025 (6)−0.0057 (6)
O30.0408 (8)0.0785 (10)0.0620 (9)−0.0078 (7)−0.0115 (7)0.0015 (7)
O4A0.0467 (10)0.0921 (14)0.0844 (13)0.0064 (9)−0.0059 (9)−0.0346 (10)
O4B0.088 (9)0.086 (8)0.088 (9)−0.014 (7)−0.012 (7)−0.027 (7)
C10.0400 (10)0.0573 (12)0.0441 (10)−0.0055 (8)−0.0075 (8)−0.0074 (8)
C20.0408 (10)0.0620 (12)0.0406 (10)−0.0089 (9)−0.0087 (8)−0.0012 (9)
C30.0474 (11)0.0727 (14)0.0510 (12)−0.0190 (10)−0.0111 (9)0.0069 (10)
C40.0452 (12)0.108 (2)0.0529 (13)−0.0264 (12)−0.0032 (10)0.0042 (13)
C50.0440 (12)0.116 (2)0.0469 (12)−0.0070 (12)0.0000 (10)−0.0109 (13)
C60.0504 (12)0.0878 (17)0.0509 (12)−0.0058 (11)−0.0005 (10)−0.0202 (11)
C70.0400 (10)0.0681 (13)0.0420 (10)−0.0106 (9)−0.0043 (8)−0.0051 (9)
C80.0392 (10)0.0619 (12)0.0413 (10)−0.0055 (9)−0.0033 (8)−0.0102 (9)
C90.0402 (10)0.0725 (14)0.0492 (11)−0.0129 (9)−0.0039 (9)−0.0116 (10)
C100.0363 (10)0.0491 (11)0.0521 (11)−0.0078 (8)−0.0054 (8)−0.0065 (8)
C110.0484 (11)0.0654 (13)0.0408 (10)−0.0062 (9)−0.0055 (8)−0.0045 (9)
C120.118 (2)0.0786 (18)0.0577 (15)−0.0077 (16)−0.0186 (15)−0.0185 (13)
C130.0555 (13)0.0899 (17)0.0500 (12)−0.0156 (12)0.0016 (10)−0.0021 (11)
C140.0683 (15)0.0767 (17)0.0809 (17)−0.0326 (13)−0.0162 (13)0.0071 (13)
C150.0542 (15)0.168 (3)0.0741 (18)−0.0068 (17)0.0147 (13)−0.0319 (19)
C160.0635 (14)0.0744 (15)0.0670 (14)−0.0040 (11)−0.0174 (11)−0.0257 (12)
C10—O3i3.295 (2)C8—C91.490 (3)
S—O4B1.463 (2)C9—C101.506 (3)
S—O4A1.464 (2)C9—H9A0.9700
S—C11.769 (2)C9—H9B0.9700
S—C161.783 (2)C11—C121.497 (3)
O1—C71.378 (2)C11—C131.501 (3)
O1—C81.382 (2)C11—H110.9800
O2—C101.332 (2)C12—H12A0.9600
O2—C111.466 (2)C12—H12B0.9600
O3—C101.199 (2)C12—H12C0.9600
C1—C81.349 (3)C13—H13A0.9600
C1—C21.448 (3)C13—H13B0.9600
C2—C71.382 (3)C13—H13C0.9600
C2—C31.412 (3)C14—H14A0.9600
C3—C41.387 (3)C14—H14B0.9600
C3—C141.502 (4)C14—H14C0.9600
C4—C51.389 (4)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C61.380 (3)C15—H15C0.9600
C5—C151.521 (3)C16—H16A0.9600
C6—C71.379 (3)C16—H16B0.9600
C6—H60.9300C16—H16C0.9600
O4B—S—O4A93.2 (8)O2—C10—C9109.90 (16)
O4B—S—C1121.5 (7)O3—C10—O3i79.52 (13)
O4A—S—C1107.56 (10)O2—C10—O3i83.17 (11)
O4B—S—C16127.3 (7)C9—C10—O3i107.38 (13)
O4A—S—C16108.31 (12)O2—C11—C12108.31 (17)
C1—S—C1697.44 (10)O2—C11—C13105.86 (16)
C7—O1—C8106.29 (15)C12—C11—C13114.3 (2)
C10—O2—C11117.50 (15)O2—C11—H11109.4
C8—C1—C2107.41 (17)C12—C11—H11109.4
C8—C1—S124.50 (15)C13—C11—H11109.4
C2—C1—S128.08 (16)C11—C12—H12A109.5
C7—C2—C3119.24 (19)C11—C12—H12B109.5
C7—C2—C1104.92 (17)H12A—C12—H12B109.5
C3—C2—C1135.8 (2)C11—C12—H12C109.5
C4—C3—C2115.5 (2)H12A—C12—H12C109.5
C4—C3—C14121.5 (2)H12B—C12—H12C109.5
C2—C3—C14123.0 (2)C11—C13—H13A109.5
C3—C4—C5124.5 (2)C11—C13—H13B109.5
C3—C4—H4117.7H13A—C13—H13B109.5
C5—C4—H4117.7C11—C13—H13C109.5
C6—C5—C4119.4 (2)H13A—C13—H13C109.5
C6—C5—C15120.6 (3)H13B—C13—H13C109.5
C4—C5—C15120.0 (3)C3—C14—H14A109.5
C7—C6—C5116.9 (2)C3—C14—H14B109.5
C7—C6—H6121.6H14A—C14—H14B109.5
C5—C6—H6121.6C3—C14—H14C109.5
O1—C7—C6124.8 (2)H14A—C14—H14C109.5
O1—C7—C2110.74 (16)H14B—C14—H14C109.5
C6—C7—C2124.4 (2)C5—C15—H15A109.5
C1—C8—O1110.62 (16)C5—C15—H15B109.5
C1—C8—C9134.01 (18)H15A—C15—H15B109.5
O1—C8—C9115.37 (17)C5—C15—H15C109.5
C8—C9—C10113.33 (16)H15A—C15—H15C109.5
C8—C9—H9A108.9H15B—C15—H15C109.5
C10—C9—H9A108.9S—C16—H16A109.5
C8—C9—H9B108.9S—C16—H16B109.5
C10—C9—H9B108.9H16A—C16—H16B109.5
H9A—C9—H9B107.7S—C16—H16C109.5
O3—C10—O2125.19 (18)H16A—C16—H16C109.5
O3—C10—C9124.88 (17)H16B—C16—H16C109.5
O4B—S—C1—C8−114.6 (9)C5—C6—C7—O1−179.9 (2)
O4A—S—C1—C8−9.3 (2)C5—C6—C7—C20.2 (3)
C16—S—C1—C8102.6 (2)C3—C2—C7—O1−178.61 (17)
O4B—S—C1—C265.6 (9)C1—C2—C7—O10.9 (2)
O4A—S—C1—C2170.83 (18)C3—C2—C7—C61.4 (3)
C16—S—C1—C2−77.2 (2)C1—C2—C7—C6−179.1 (2)
C8—C1—C2—C7−0.5 (2)C2—C1—C8—O1−0.2 (2)
S—C1—C2—C7179.39 (15)S—C1—C8—O1179.98 (13)
C8—C1—C2—C3179.0 (2)C2—C1—C8—C9179.6 (2)
S—C1—C2—C3−1.2 (4)S—C1—C8—C9−0.2 (3)
C7—C2—C3—C4−1.7 (3)C7—O1—C8—C10.7 (2)
C1—C2—C3—C4179.0 (2)C7—O1—C8—C9−179.11 (17)
C7—C2—C3—C14177.9 (2)C1—C8—C9—C10−62.5 (3)
C1—C2—C3—C14−1.5 (4)O1—C8—C9—C10117.28 (19)
C2—C3—C4—C50.6 (3)C11—O2—C10—O31.4 (3)
C14—C3—C4—C5−179.0 (2)C11—O2—C10—C9179.47 (16)
C3—C4—C5—C60.9 (4)C11—O2—C10—O3i73.42 (14)
C3—C4—C5—C15−179.2 (2)C8—C9—C10—O3−21.3 (3)
C4—C5—C6—C7−1.3 (3)C8—C9—C10—O2160.60 (17)
C15—C5—C6—C7178.8 (2)C8—C9—C10—O3i−110.50 (16)
C8—O1—C7—C6179.0 (2)C10—O2—C11—C1292.1 (2)
C8—O1—C7—C2−1.0 (2)C10—O2—C11—C13−144.89 (18)
D—H···AD—HH···AD···AD—H···A
C9—H9B···Cgii0.972.993.646 (4)126
C14—H14A···O4Aiii0.962.573.504 (3)165
C15—H15C···O4Biv0.962.543.343 (5)142
C16—H16A···O4Av0.962.393.333 (3)168
C16—H16A···O4Av0.962.393.333 (3)168
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C9—H9B⋯Cgi0.972.993.646 (4)126
C14—H14A⋯O4Aii0.962.573.504 (3)165
C15—H15C⋯O4Biii0.962.543.343 (5)142
C16—H16A⋯O4Aiv0.962.393.333 (3)168
C16—H16A⋯O4Aiv0.962.393.333 (3)168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg is the centroid of C2–C7 benzene ring.

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Isopropyl 2-(5-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Authors:  Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-10-09
  2 in total

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