Literature DB >> 21578444

(E)-3-(Biphenyl-4-yl)-1-(3-bromo-phen-yl)prop-2-en-1-one.

Grzegorz Dutkiewicz, C S Chidan Kumar, H S Yathirajan, B Narayana, Maciej Kubicki.   

Abstract

In the title compound, C(21)H(15)BrO, there are two planar rings connected through a conjugated double bond. As it crystallizes in a non-centrosymmetric space group it can be regarded as a good candidate for non-linear optical applications. The mol-ecule adopts an E configuration and the C-C=C-C torsion angle is 177.1 (4)°. The overall conformation of the compound may be described by the values of dihedral angles between the approximately planar parts. The terminal rings are twisted by an angle of 51.52 (9)°, while the biphenyl part is almost planar, the dihedral angle between the planes of the rings being 4.44 (17)°. The unit cell has one long dimension, above 35 Å, characteristic also of a majority of related compounds. The mol-ecules pack head-to-tail along this direction. C-H⋯π inter-actions are observed in the crystal structure.

Entities:  

Year:  2009        PMID： 21578444      PMCID： PMC2971314          DOI： 10.1107/S1600536809043384

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


Related literature

For applications of chalcones, see: Cho et al. (1996 ▶); Dinkova-Kostova et al., (1998 ▶); Fichou et al. (1988 ▶); Liu et al. (2003 ▶); Nielson et al. (1998 ▶); Rajas et al. (2002 ▶); Sarojini et al. (2006 ▶). For related structures, see: Fischer et al. (2007a ▶,b ▶,c ▶); Moorthi et al. (2007 ▶); Sarojini et al. (2007 ▶).

Experimental

Crystal data

C21H15BrO M = 363.24 Orthorhombic, a = 6.092 (1) Å b = 7.295 (1) Å c = 36.619 (2) Å V = 1627.4 (4) Å3 Z = 4 Mo Kα radiation μ = 2.53 mm−1 T = 295 K 0.4 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2006 ▶) T min = 0.632, T max = 1.000 5236 measured reflections 2766 independent reflections 2209 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.085 S = 1.05 2766 reflections 208 parameters 1 restraint H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.45 e Å−3 Absolute structure: Flack (1983 ▶), 1133 Friedel pairs Flack parameter: 0.059 (11) Data collection: CrysAlis Pro (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043384/nk2009sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043384/nk2009Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H15BrOF(000) = 736
Mr = 363.24Dx = 1.483 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2900 reflections
a = 6.092 (1) Åθ = 2.2–26.8°
b = 7.295 (1) ŵ = 2.53 mm−1
c = 36.619 (2) ÅT = 295 K
V = 1627.4 (4) Å3Prism, colourless
Z = 40.4 × 0.2 × 0.2 mm
Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer2766 independent reflections
Radiation source: Enhance (Mo) X-ray Source2209 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 8.1929 pixels mm-1θmax = 26.9°, θmin = 2.2°
ω scansh = −5→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)k = −5→9
Tmin = 0.632, Tmax = 1.000l = −45→41
5236 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.085w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2766 reflectionsΔρmax = 0.25 e Å−3
208 parametersΔρmin = −0.45 e Å−3
1 restraintAbsolute structure: Flack (1983), 1133 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.059 (11)
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
C10.6509 (7)0.7425 (7)0.79823 (11)0.0516 (11)
H10.59270.73790.77480.062*
C20.8449 (7)0.8289 (5)0.80447 (11)0.0532 (10)
H20.91940.88470.78530.064*
C30.9320 (7)0.8337 (5)0.83967 (9)0.0430 (9)
H31.06450.89380.84370.052*
C40.8253 (6)0.7506 (5)0.86911 (10)0.0333 (7)
C50.6238 (6)0.6661 (4)0.86149 (11)0.0407 (9)
H50.54540.61200.88040.049*
C60.5403 (7)0.6612 (5)0.82712 (12)0.0504 (10)
H60.40720.60260.82290.061*
C70.9218 (6)0.7517 (5)0.90615 (9)0.0302 (7)
C81.1289 (5)0.8263 (5)0.91272 (10)0.0376 (8)
H81.20810.87590.89340.045*
C91.2194 (6)0.8281 (5)0.94747 (11)0.0390 (8)
H91.35860.87760.95080.047*
C101.1075 (6)0.7580 (5)0.97729 (10)0.0364 (8)
C110.9024 (6)0.6836 (5)0.97075 (10)0.0424 (9)
H110.82340.63460.99020.051*
C120.8120 (6)0.6801 (5)0.93638 (11)0.0398 (8)
H120.67380.62840.93320.048*
C131.2154 (6)0.7575 (6)1.01312 (11)0.0449 (9)
H131.36130.79521.01360.054*
C141.1287 (7)0.7096 (6)1.04483 (11)0.0494 (10)
H140.98150.67611.04610.059*
C151.2648 (7)0.7089 (5)1.07855 (11)0.0476 (9)
O161.4619 (5)0.6988 (4)1.07694 (8)0.0696 (9)
C171.1481 (6)0.7302 (5)1.11410 (10)0.0412 (8)
C181.2662 (6)0.6895 (4)1.14615 (10)0.0380 (8)
H181.40690.64051.14470.046*
C191.1730 (6)0.7225 (5)1.17930 (11)0.0435 (8)
C200.9649 (8)0.7894 (5)1.18260 (12)0.0515 (10)
H200.90280.80921.20550.062*
C210.8486 (6)0.8273 (5)1.15093 (14)0.0487 (11)
H210.70740.87511.15260.058*
C220.9371 (7)0.7956 (5)1.11731 (11)0.0477 (9)
H220.85450.81831.09640.057*
Br231.33920 (7)0.67882 (6)1.222156 (16)0.06635 (16)
U11U22U33U12U13U23
C10.071 (3)0.044 (2)0.040 (2)0.008 (2)−0.014 (2)−0.0040 (19)
C20.071 (3)0.054 (2)0.035 (2)−0.006 (2)0.0032 (17)0.0005 (16)
C30.042 (2)0.054 (2)0.0327 (18)−0.0073 (18)0.0040 (14)−0.0016 (15)
C40.038 (2)0.0254 (16)0.0363 (17)0.0042 (15)0.0029 (14)−0.0008 (13)
C50.044 (2)0.0343 (19)0.044 (2)−0.0048 (15)−0.0018 (15)0.0043 (15)
C60.057 (3)0.045 (2)0.049 (2)−0.0094 (18)−0.0123 (19)0.0004 (18)
C70.0334 (19)0.0240 (15)0.0332 (16)0.0007 (14)0.0039 (13)0.0004 (12)
C80.036 (2)0.040 (2)0.0362 (18)−0.0046 (15)0.0024 (13)0.0039 (14)
C90.0300 (19)0.041 (2)0.046 (2)−0.0043 (15)−0.0044 (15)−0.0022 (15)
C100.037 (2)0.0369 (18)0.0354 (18)−0.0008 (15)−0.0013 (13)−0.0026 (15)
C110.043 (2)0.048 (2)0.036 (2)−0.0089 (17)0.0034 (15)0.0064 (16)
C120.031 (2)0.048 (2)0.0408 (18)−0.0061 (17)−0.0008 (13)−0.0014 (15)
C130.050 (2)0.042 (2)0.043 (2)0.0038 (18)−0.0044 (18)−0.0012 (17)
C140.043 (2)0.066 (3)0.038 (2)−0.0047 (19)−0.0095 (16)−0.0006 (18)
C150.046 (2)0.056 (2)0.040 (2)−0.0019 (19)−0.0052 (17)−0.0007 (17)
O160.0414 (18)0.118 (3)0.0490 (17)0.0122 (17)−0.0012 (13)−0.0013 (16)
C170.037 (2)0.046 (2)0.0412 (19)−0.0037 (17)−0.0081 (14)−0.0013 (16)
C180.0331 (19)0.0402 (19)0.0406 (19)−0.0016 (15)−0.0073 (14)−0.0010 (15)
C190.041 (2)0.048 (2)0.042 (2)−0.0057 (18)−0.0078 (15)−0.0001 (16)
C200.051 (3)0.058 (2)0.045 (2)−0.001 (2)0.0027 (17)−0.0004 (18)
C210.035 (2)0.051 (2)0.060 (3)−0.0022 (18)−0.0076 (17)0.000 (2)
C220.044 (2)0.047 (2)0.052 (2)−0.0032 (18)−0.0090 (18)0.0020 (16)
Br230.0653 (3)0.0941 (3)0.03960 (19)0.0043 (2)−0.0142 (2)0.0021 (3)
C1—C21.358 (6)C11—C121.374 (5)
C1—C61.387 (6)C11—H110.9300
C1—H10.9300C12—H120.9300
C2—C31.394 (5)C13—C141.323 (6)
C2—H20.9300C13—H130.9300
C3—C41.397 (5)C14—C151.487 (5)
C3—H30.9300C14—H140.9300
C4—C51.401 (5)C15—O161.204 (5)
C4—C71.478 (5)C15—C171.492 (6)
C5—C61.358 (5)C17—C221.376 (6)
C5—H50.9300C17—C181.408 (5)
C6—H60.9300C18—C191.361 (5)
C7—C121.395 (5)C18—H180.9300
C7—C81.395 (5)C19—C201.364 (6)
C8—C91.387 (5)C19—Br231.894 (4)
C8—H80.9300C20—C211.387 (6)
C9—C101.385 (5)C20—H200.9300
C9—H90.9300C21—C221.364 (6)
C10—C111.383 (5)C21—H210.9300
C10—C131.468 (5)C22—H220.9300
C2—C1—C6119.5 (4)C10—C11—H11119.1
C2—C1—H1120.3C11—C12—C7121.9 (3)
C6—C1—H1120.2C11—C12—H12119.1
C1—C2—C3119.9 (4)C7—C12—H12119.1
C1—C2—H2120.0C14—C13—C10127.3 (4)
C3—C2—H2120.1C14—C13—H13116.3
C2—C3—C4121.7 (4)C10—C13—H13116.3
C2—C3—H3119.2C13—C14—C15120.4 (4)
C4—C3—H3119.2C13—C14—H14119.8
C3—C4—C5116.4 (3)C15—C14—H14119.8
C3—C4—C7121.4 (3)O16—C15—C14121.0 (4)
C5—C4—C7122.2 (3)O16—C15—C17121.6 (3)
C6—C5—C4121.6 (4)C14—C15—C17117.3 (4)
C6—C5—H5119.2C22—C17—C18118.6 (4)
C4—C5—H5119.2C22—C17—C15123.8 (3)
C5—C6—C1120.9 (4)C18—C17—C15117.5 (3)
C5—C6—H6119.5C19—C18—C17119.5 (4)
C1—C6—H6119.5C19—C18—H18120.2
C12—C7—C8116.3 (3)C17—C18—H18120.2
C12—C7—C4122.4 (3)C18—C19—C20122.0 (4)
C8—C7—C4121.3 (3)C18—C19—Br23119.1 (3)
C9—C8—C7121.4 (3)C20—C19—Br23118.9 (3)
C9—C8—H8119.3C19—C20—C21118.2 (4)
C7—C8—H8119.3C19—C20—H20120.9
C10—C9—C8121.6 (3)C21—C20—H20120.9
C10—C9—H9119.2C22—C21—C20121.2 (4)
C8—C9—H9119.2C22—C21—H21119.4
C11—C10—C9116.9 (3)C20—C21—H21119.4
C11—C10—C13124.0 (3)C21—C22—C17120.4 (4)
C9—C10—C13119.0 (3)C21—C22—H22119.8
C12—C11—C10121.9 (3)C17—C22—H22119.8
C12—C11—H11119.1
C6—C1—C2—C30.6 (6)C4—C7—C12—C11−179.3 (3)
C1—C2—C3—C40.3 (6)C11—C10—C13—C14−9.0 (7)
C2—C3—C4—C5−1.4 (5)C9—C10—C13—C14174.4 (4)
C2—C3—C4—C7178.2 (4)C10—C13—C14—C15177.1 (4)
C3—C4—C5—C61.7 (5)C13—C14—C15—O16−21.7 (6)
C7—C4—C5—C6−178.0 (3)C13—C14—C15—C17155.4 (4)
C4—C5—C6—C1−0.9 (6)O16—C15—C17—C22160.0 (4)
C2—C1—C6—C5−0.3 (6)C14—C15—C17—C22−17.1 (5)
C3—C4—C7—C12175.8 (3)O16—C15—C17—C18−16.7 (6)
C5—C4—C7—C12−4.6 (5)C14—C15—C17—C18166.3 (3)
C3—C4—C7—C8−3.8 (5)C22—C17—C18—C19−2.6 (5)
C5—C4—C7—C8175.8 (3)C15—C17—C18—C19174.2 (3)
C12—C7—C8—C90.1 (5)C17—C18—C19—C201.9 (6)
C4—C7—C8—C9179.7 (3)C17—C18—C19—Br23−176.8 (3)
C7—C8—C9—C10−0.7 (5)C18—C19—C20—C21−1.1 (6)
C8—C9—C10—C110.9 (5)Br23—C19—C20—C21177.6 (3)
C8—C9—C10—C13177.7 (4)C19—C20—C21—C221.2 (6)
C9—C10—C11—C12−0.5 (5)C20—C21—C22—C17−2.0 (6)
C13—C10—C11—C12−177.1 (4)C18—C17—C22—C212.7 (6)
C10—C11—C12—C7−0.2 (6)C15—C17—C22—C21−173.9 (3)
C8—C7—C12—C110.3 (5)
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.932.853.583 (5)137
C6—H6···Cg1ii0.932.783.516 (5)137
C9—H9···Cg2i0.932.873.544 (5)131
C12—H12···Cg2ii0.932.973.655 (5)131
C21—H21···Cg3iii0.932.833.505 (5)131
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯Cg1i0.932.853.583 (5)137
C6—H6⋯Cg1ii0.932.783.516 (5)137
C9—H9⋯Cg2i0.932.873.544 (5)131
C12—H12⋯Cg2ii0.932.973.655 (5)131
C21—H21⋯Cg3iii0.932.833.505 (5)131

Symmetry codes: (i) ; (ii) ; (iii) . Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7–C12 and C17–C22 rings, respectively.

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