Literature DB >> 21202897

(E)-1-[4-(Methyl-sulfan-yl)phen-yl]-3-phenyl-prop-2-en-1-one.

A Thiruvalluvar, M Subramanyam, R J Butcher, T Karabasanagouda, A V Adhikari.   

Abstract

In the title mol-ecule, C(16)H(14)OS, the dihedral angle between the phenyl and benzene rings is 3.81 (15)°. The H atoms of the central enone group are trans. The propenone unit makes dihedral angles of 11.73 (18) and 11.62 (17)° with the benzene and phenyl rings, respectively. The crystal structure is stabilized by weak C-H⋯O and C-H⋯π inter-actions.

Entities:  

Year:  2008        PMID： 21202897      PMCID： PMC2961704          DOI： 10.1107/S1600536808017200

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


Related literature

For related crystal structures, see Sathiya Moorthi et al. (2005 ▶); Moorthi et al. (2005 ▶); Thiruvalluvar et al. (2007a ▶,b ▶).

Experimental

Crystal data

C16H14OS M = 254.34 Orthorhombic, a = 5.6106 (4) Å b = 7.6239 (7) Å c = 30.477 (2) Å V = 1303.64 (17) Å3 Z = 4 Mo Kα radiation μ = 0.23 mm−1 T = 200 (2) K 0.49 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Gemini R diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.849, T max = 1.000 (expected range = 0.820–0.966) 8924 measured reflections 4060 independent reflections 3180 reflections with I > 2σ(I) R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.077 wR(F 2) = 0.181 S = 1.11 4060 reflections 163 parameters H-atom parameters constrained Δρmax = 0.69 e Å−3 Δρmin = −0.38 e Å−3 Absolute structure: Flack (1983 ▶), 1314 Friedel pairs Flack parameter: 0.11 (16) Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017200/wn2267sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017200/wn2267Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H14OSDx = 1.296 Mg m−3
Mr = 254.34Melting point: 396(1) K
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3999 reflections
a = 5.6106 (4) Åθ = 4.7–32.4º
b = 7.6239 (7) ŵ = 0.23 mm−1
c = 30.477 (2) ÅT = 200 (2) K
V = 1303.64 (17) Å3Needle, colourless
Z = 40.49 × 0.18 × 0.15 mm
F000 = 536
Oxford Diffraction Gemini diffractometer4060 independent reflections
Radiation source: fine-focus sealed tube3180 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.069
Detector resolution: 10.5081 pixels mm-1θmax = 32.5º
T = 200(2) Kθmin = 4.7º
φ and ω scansh = −6→8
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −11→10
Tmin = 0.849, Tmax = 1.000l = −45→38
8924 measured reflections
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.077  w = 1/[σ2(Fo2) + (0.0605P)2 + 1.4543P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.182(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.69 e Å−3
4060 reflectionsΔρmin = −0.38 e Å−3
163 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1314 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.11 (16)
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 > 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
S40.48075 (18)0.98501 (13)−0.09063 (3)0.0418 (3)
O10.8645 (4)1.0222 (4)0.11787 (7)0.0411 (8)
C10.6679 (5)0.9800 (4)0.10480 (9)0.0284 (8)
C20.4803 (6)0.9187 (4)0.13565 (9)0.0300 (8)
C30.5318 (6)0.8989 (4)0.17807 (9)0.0273 (8)
C40.7257 (8)1.0997 (6)−0.11513 (11)0.0481 (13)
C110.3725 (6)0.8391 (4)0.21292 (9)0.0269 (8)
C120.4425 (5)0.8603 (4)0.25687 (9)0.0284 (8)
C130.2984 (7)0.8019 (5)0.29078 (10)0.0349 (10)
C140.0835 (7)0.7219 (5)0.28169 (11)0.0374 (10)
C150.0098 (7)0.6998 (4)0.23848 (10)0.0335 (9)
C160.1525 (6)0.7588 (4)0.20435 (10)0.0306 (9)
C210.6093 (5)0.9893 (4)0.05707 (9)0.0239 (7)
C220.7753 (5)1.0701 (4)0.02917 (10)0.0285 (8)
C230.7412 (6)1.0748 (4)−0.01573 (10)0.0296 (8)
C240.5389 (6)0.9955 (4)−0.03416 (9)0.0281 (8)
C250.3704 (5)0.9185 (4)−0.00654 (10)0.0293 (8)
C260.4044 (6)0.9151 (4)0.03850 (10)0.0300 (8)
H20.324420.893740.125180.0360*
H30.690180.926870.186610.0328*
H4A0.707021.09997−0.147100.0720*
H4B0.875271.04105−0.107340.0720*
H4C0.728781.22076−0.104340.0720*
H120.590230.915230.263410.0340*
H130.347670.817040.320360.0419*
H14−0.014520.681750.305040.0449*
H15−0.138080.644310.232330.0402*
H160.100640.744590.174890.0367*
H220.913771.122620.041380.0341*
H230.854421.13149−0.034070.0356*
H250.230770.86768−0.018750.0351*
H260.288020.862250.056870.0360*
U11U22U33U12U13U23
S40.0460 (5)0.0497 (5)0.0297 (3)−0.0035 (5)−0.0048 (3)−0.0008 (3)
O10.0278 (12)0.0601 (17)0.0353 (11)−0.0141 (13)−0.0040 (9)0.0017 (11)
C10.0259 (14)0.0295 (15)0.0297 (12)−0.0040 (13)0.0011 (10)−0.0007 (11)
C20.0243 (14)0.0349 (15)0.0308 (12)−0.0088 (13)0.0007 (11)0.0004 (11)
C30.0215 (14)0.0254 (13)0.0350 (13)−0.0010 (12)0.0022 (11)−0.0006 (11)
C40.051 (2)0.059 (3)0.0342 (16)−0.005 (2)0.0029 (15)0.0084 (17)
C110.0248 (14)0.0252 (14)0.0307 (13)0.0026 (12)0.0026 (11)0.0010 (11)
C120.0218 (15)0.0295 (15)0.0338 (14)0.0040 (11)−0.0026 (11)−0.0009 (11)
C130.0377 (18)0.0378 (18)0.0293 (14)0.0044 (15)0.0003 (13)0.0019 (12)
C140.0379 (19)0.0348 (18)0.0396 (17)0.0129 (14)0.0114 (13)0.0081 (14)
C150.0303 (16)0.0246 (14)0.0456 (16)−0.0027 (14)0.0050 (14)0.0008 (11)
C160.0262 (15)0.0323 (16)0.0332 (14)0.0015 (13)−0.0002 (12)−0.0002 (12)
C210.0210 (12)0.0210 (12)0.0297 (12)0.0003 (11)0.0004 (9)0.0002 (11)
C220.0213 (13)0.0300 (15)0.0341 (14)−0.0069 (12)0.0002 (11)0.0004 (12)
C230.0255 (14)0.0295 (15)0.0339 (14)−0.0023 (12)0.0034 (11)0.0025 (12)
C240.0326 (15)0.0220 (12)0.0297 (12)0.0040 (13)−0.0023 (10)0.0004 (11)
C250.0202 (13)0.0319 (15)0.0357 (14)−0.0070 (12)−0.0032 (11)−0.0034 (12)
C260.0258 (15)0.0316 (15)0.0327 (14)−0.0035 (13)0.0022 (11)0.0001 (12)
S4—C41.792 (4)C24—C251.395 (4)
S4—C241.754 (3)C25—C261.386 (4)
O1—C11.216 (4)C2—H20.9500
C1—C21.487 (4)C3—H30.9500
C1—C211.493 (4)C4—H4A0.9800
C2—C31.333 (4)C4—H4B0.9800
C3—C111.461 (4)C4—H4C0.9800
C11—C121.405 (4)C12—H120.9500
C11—C161.402 (5)C13—H130.9500
C12—C131.386 (4)C14—H140.9500
C13—C141.379 (5)C15—H150.9500
C14—C151.391 (5)C16—H160.9500
C15—C161.388 (5)C22—H220.9500
C21—C221.404 (4)C23—H230.9500
C21—C261.401 (4)C25—H250.9500
C22—C231.382 (4)C26—H260.9500
C23—C241.403 (5)
S4···H16i3.1800H2···C262.6800
O1···H2ii2.7700H2···H162.2700
O1···H32.4200H2···H262.1100
O1···H222.4700H3···O12.4200
O1···H4Ciii2.8600H3···C15ii2.9500
O1···H14iv2.7800H3···C16ii2.9400
C3···C13iv3.354 (5)H3···H122.4100
C3···C14iv3.497 (5)H3···C13iv2.9400
C3···C15ii3.590 (5)H3···C14iv2.7600
C12···C15ii3.456 (5)H4A···C14x3.0300
C13···C3v3.354 (5)H4A···H14x2.4600
C14···C3v3.497 (5)H4B···C232.9000
C15···C12vi3.456 (5)H4B···H232.3400
C15···C3vi3.590 (5)H4C···C232.9200
C2···H162.7800H4C···H232.3600
C2···H262.6700H4C···O1ix2.8600
C4···H232.5900H12···C15ii2.9700
C12···H15vii2.7800H12···H32.4100
C12···H15ii2.9700H14···H4Aviii2.4600
C13···H15vii2.8500H14···O1v2.7800
C13···H3v2.9400H15···C12vi2.9700
C14···H3v2.7600H15···C12xi2.7800
C14···H4Aviii3.0300H15···C13xi2.8500
C15···H3vi2.9500H16···C22.7800
C15···H12vi2.9700H16···H22.2700
C16···H22.7900H16···S4xii3.1800
C16···H3vi2.9400H22···O12.4700
C21···H25i3.0400H22···C23iii3.0500
C23···H4B2.9000H22···C24iii3.0000
C23···H4C2.9200H23···C42.5900
C23···H22ix3.0500H23···H4B2.3400
C24···H22ix3.0000H23···H4C2.3600
C25···H25i3.0700H25···C21xii3.0400
C26···H22.6800H25···C25xii3.0700
C26···H25i2.8900H25···C26xii2.8900
H2···O1vi2.7700H26···C22.6700
H2···C162.7900H26···H22.1100
C4—S4—C24104.13 (16)C2—C3—H3116.00
O1—C1—C2121.2 (3)C11—C3—H3116.00
O1—C1—C21120.4 (3)S4—C4—H4A109.00
C2—C1—C21118.4 (2)S4—C4—H4B109.00
C1—C2—C3119.7 (3)S4—C4—H4C109.00
C2—C3—C11127.4 (3)H4A—C4—H4B109.00
C3—C11—C12119.1 (3)H4A—C4—H4C109.00
C3—C11—C16122.6 (3)H4B—C4—H4C109.00
C12—C11—C16118.3 (3)C11—C12—H12120.00
C11—C12—C13120.7 (3)C13—C12—H12120.00
C12—C13—C14120.2 (3)C12—C13—H13120.00
C13—C14—C15120.3 (3)C14—C13—H13120.00
C14—C15—C16119.9 (3)C13—C14—H14120.00
C11—C16—C15120.7 (3)C15—C14—H14120.00
C1—C21—C22117.7 (3)C14—C15—H15120.00
C1—C21—C26123.7 (3)C16—C15—H15120.00
C22—C21—C26118.5 (3)C11—C16—H16120.00
C21—C22—C23121.3 (3)C15—C16—H16120.00
C22—C23—C24119.8 (3)C21—C22—H22119.00
S4—C24—C23124.3 (2)C23—C22—H22119.00
S4—C24—C25116.5 (2)C22—C23—H23120.00
C23—C24—C25119.2 (3)C24—C23—H23120.00
C24—C25—C26120.8 (3)C24—C25—H25120.00
C21—C26—C25120.4 (3)C26—C25—H25120.00
C1—C2—H2120.00C21—C26—H26120.00
C3—C2—H2120.00C25—C26—H26120.00
C4—S4—C24—C23−1.6 (3)C11—C12—C13—C140.0 (5)
C4—S4—C24—C25178.6 (3)C12—C13—C14—C15−0.2 (6)
O1—C1—C2—C3−4.2 (5)C13—C14—C15—C16−0.2 (5)
C21—C1—C2—C3176.0 (3)C14—C15—C16—C110.7 (5)
O1—C1—C21—C22−8.6 (4)C1—C21—C22—C23176.1 (3)
O1—C1—C21—C26168.4 (3)C26—C21—C22—C23−1.0 (5)
C2—C1—C21—C22171.3 (3)C1—C21—C26—C25−175.5 (3)
C2—C1—C21—C26−11.8 (4)C22—C21—C26—C251.4 (5)
C1—C2—C3—C11−179.5 (3)C21—C22—C23—C24−0.9 (5)
C2—C3—C11—C12−167.1 (3)C22—C23—C24—S4−177.5 (2)
C2—C3—C11—C1613.8 (5)C22—C23—C24—C252.4 (5)
C3—C11—C12—C13−178.7 (3)S4—C24—C25—C26177.9 (2)
C16—C11—C12—C130.5 (5)C23—C24—C25—C26−1.9 (5)
C3—C11—C16—C15178.3 (3)C24—C25—C26—C210.0 (5)
C12—C11—C16—C15−0.9 (5)
D—H···AD—HH···AD···AD—H···A
C3—H3···O10.952.422.781 (4)102
C12—H12···Cg1iv0.952.993.704 (3)133
C15—H15···Cg1xi0.952.893.488 (3)122
C25—H25···Cg2xii0.952.903.562 (3)127
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯O10.952.422.781 (4)102
C12—H12⋯Cg1i0.952.993.704 (3)133
C15—H15⋯Cg1ii0.952.893.488 (3)122
C25—H25⋯Cg2iii0.952.903.562 (3)127

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

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