Literature DB >> 25161590

(E)-1-([1,1'-Biphen-yl]-4-yl)-3-(2-methyl-phen-yl)prop-2-en-1-one.

D Shanthi1, T Vidhya Sagar1, M Kayalvizhi2, G Vasuki2, A Thiruvalluvar3.   

Abstract

In the title mol-ecule, C22H18O, the o-tolyl ring is connected through a conjugated double bond. The mol-ecule adopts an E conformation and the C-C=C-C torsion angle is 178.77 (13)°. The overall conformation may be described by the values of dihedral angles between the different planes. The terminal rings are twisted by an angle of 54.75 (8)°, while the biphenyl part is not planar, the dihedral angle between the planes of the rings being 40.65 (8)°. The dihedral angle between the benzene rings is 14.10 (7)°. There are three weak C-H⋯π inter-actions found in the crystal structure. No classic hydrogen bonds are observed.

Entities:  

Keywords:  crystal structure

Year:  2014        PMID： 25161590      PMCID： PMC4120573          DOI： 10.1107/S1600536814014317

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


Related literature

For the bioactivity of chalcones, see: Dimmock et al. (1999 ▶). For biological applications of chalcones, see: Opletalova (2000 ▶); Opletalova & Sedivy (1999 ▶). For chalcones as non-linear optical materials, see: Fichou et al. (1988 ▶); Goto et al. (1991 ▶). For further applications of chalcones, see: Sarojini et al. (2006 ▶). For the crystal structures of related compounds, see: Betz et al. (2011a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H18O M = 298.36 Triclinic, a = 7.6396 (3) Å b = 9.9106 (4) Å c = 11.9263 (4) Å α = 103.166 (2)° β = 104.713 (2)° γ = 103.308 (2)° V = 809.66 (6) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 273 K 0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.908, T max = 1.000 18636 measured reflections 4534 independent reflections 3291 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.151 S = 1.06 4534 reflections 209 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014317/jj2188sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014317/jj2188Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814014317/jj2188Isup3.cdx Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814014317/jj2188Isup4.cml CCDC reference: 977614 Additional supporting information: crystallographic information; 3D view; checkCIF report
C22H18OZ = 2
Mr = 298.36F(000) = 316
Triclinic, P1Dx = 1.224 Mg m−3
Hall symbol: -P 1Melting point: 393 K
a = 7.6396 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9106 (4) ÅCell parameters from 7102 reflections
c = 11.9263 (4) Åθ = 2.8–26.3°
α = 103.166 (2)°µ = 0.07 mm−1
β = 104.713 (2)°T = 273 K
γ = 103.308 (2)°Block, colourless
V = 809.66 (6) Å30.40 × 0.35 × 0.30 mm
Bruker Kappa APEXII CCD diffractometer4534 independent reflections
Radiation source: fine-focus sealed tube3291 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω and φ scanθmax = 29.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −10→10
Tmin = 0.908, Tmax = 1.000k = −13→13
18636 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.073P)2 + 0.1155P] where P = (Fo2 + 2Fc2)/3
4534 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
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
xyzUiso*/Ueq
O10.37261 (17)0.60727 (11)0.09681 (9)0.0666 (4)
C10.1424 (2)0.25545 (16)−0.31150 (12)0.0598 (5)
C20.02836 (17)0.14897 (13)−0.26587 (10)0.0413 (3)
C3−0.08815 (19)0.01392 (14)−0.34508 (11)0.0489 (4)
C4−0.1977 (2)−0.08585 (15)−0.30810 (13)0.0555 (4)
C5−0.1963 (2)−0.05199 (16)−0.18929 (14)0.0594 (5)
C6−0.0836 (2)0.08192 (15)−0.10901 (12)0.0513 (4)
C70.02996 (17)0.18386 (13)−0.14437 (10)0.0396 (3)
C80.14997 (19)0.32479 (13)−0.05697 (10)0.0447 (3)
C90.13129 (18)0.38670 (14)0.04796 (11)0.0477 (4)
C100.26312 (18)0.52846 (14)0.13063 (10)0.0448 (4)
C110.26370 (17)0.57385 (13)0.25891 (10)0.0404 (3)
C120.1919 (2)0.47482 (14)0.31431 (11)0.0478 (4)
C130.20814 (19)0.51956 (14)0.43612 (11)0.0476 (4)
C140.29252 (17)0.66487 (13)0.50571 (10)0.0397 (3)
C150.35955 (18)0.76420 (13)0.44861 (10)0.0429 (3)
C160.34808 (18)0.71934 (13)0.32782 (10)0.0427 (3)
C170.30998 (17)0.71263 (14)0.63651 (10)0.0422 (3)
C180.35892 (19)0.62864 (15)0.71095 (11)0.0481 (4)
C190.3769 (2)0.67267 (17)0.83319 (12)0.0560 (5)
C200.3468 (2)0.80073 (19)0.88272 (12)0.0636 (5)
C210.2975 (3)0.8849 (2)0.81035 (13)0.0695 (6)
C220.2805 (2)0.84196 (17)0.68813 (12)0.0574 (5)
H1A0.121550.21253−0.396370.0897*
H1B0.274940.28020−0.266780.0897*
H1C0.103730.34179−0.300560.0897*
H3−0.09204−0.00968−0.425940.0587*
H4−0.27269−0.17613−0.363090.0666*
H5−0.27074−0.11885−0.163530.0712*
H6−0.083500.10469−0.028910.0615*
H80.249370.37590−0.077330.0536*
H90.031870.339390.070400.0573*
H120.132320.377510.268990.0574*
H130.161900.451380.472110.0572*
H150.412930.862380.492670.0514*
H160.397190.787010.292260.0512*
H180.379880.541580.678130.0576*
H190.409530.615180.881770.0672*
H200.359560.830640.964950.0763*
H210.275510.971290.843710.0834*
H220.248910.900490.640330.0688*
U11U22U33U12U13U23
O10.0822 (8)0.0610 (6)0.0424 (5)−0.0025 (5)0.0263 (5)0.0071 (4)
C10.0701 (10)0.0586 (8)0.0426 (7)0.0047 (7)0.0249 (6)0.0080 (6)
C20.0422 (6)0.0426 (6)0.0362 (5)0.0136 (5)0.0117 (4)0.0071 (4)
C30.0517 (8)0.0478 (7)0.0379 (6)0.0152 (6)0.0086 (5)0.0020 (5)
C40.0492 (8)0.0431 (7)0.0561 (8)0.0065 (6)0.0045 (6)0.0030 (6)
C50.0536 (8)0.0522 (8)0.0661 (9)0.0044 (6)0.0186 (7)0.0191 (7)
C60.0555 (8)0.0524 (8)0.0445 (6)0.0119 (6)0.0196 (6)0.0130 (5)
C70.0407 (6)0.0410 (6)0.0352 (5)0.0135 (5)0.0112 (4)0.0082 (4)
C80.0502 (7)0.0439 (6)0.0354 (5)0.0097 (5)0.0137 (5)0.0084 (5)
C90.0459 (7)0.0517 (7)0.0371 (6)0.0085 (6)0.0139 (5)0.0038 (5)
C100.0481 (7)0.0484 (7)0.0341 (5)0.0138 (5)0.0123 (5)0.0075 (5)
C110.0410 (6)0.0434 (6)0.0329 (5)0.0127 (5)0.0100 (4)0.0066 (4)
C120.0564 (8)0.0383 (6)0.0404 (6)0.0067 (5)0.0159 (5)0.0040 (5)
C130.0565 (8)0.0421 (7)0.0408 (6)0.0070 (6)0.0183 (5)0.0114 (5)
C140.0398 (6)0.0430 (6)0.0340 (5)0.0128 (5)0.0108 (4)0.0083 (4)
C150.0497 (7)0.0358 (6)0.0359 (5)0.0099 (5)0.0094 (5)0.0057 (4)
C160.0482 (7)0.0406 (6)0.0362 (5)0.0100 (5)0.0116 (5)0.0120 (4)
C170.0395 (6)0.0481 (7)0.0347 (5)0.0104 (5)0.0121 (4)0.0077 (5)
C180.0505 (7)0.0489 (7)0.0420 (6)0.0085 (6)0.0166 (5)0.0136 (5)
C190.0536 (8)0.0686 (9)0.0429 (7)0.0081 (7)0.0165 (6)0.0212 (6)
C200.0582 (9)0.0913 (12)0.0376 (6)0.0204 (8)0.0194 (6)0.0108 (7)
C210.0794 (11)0.0832 (11)0.0489 (8)0.0428 (9)0.0238 (7)0.0041 (7)
C220.0673 (9)0.0667 (9)0.0428 (7)0.0353 (8)0.0169 (6)0.0116 (6)
O1—C101.2192 (18)C19—C201.369 (2)
C1—C21.499 (2)C20—C211.375 (3)
C2—C31.3873 (18)C21—C221.385 (2)
C2—C71.4072 (16)C1—H1A0.9600
C3—C41.370 (2)C1—H1B0.9600
C4—C51.376 (2)C1—H1C0.9600
C5—C61.377 (2)C3—H30.9300
C6—C71.388 (2)C4—H40.9300
C7—C81.4628 (17)C5—H50.9300
C8—C91.3207 (17)C6—H60.9300
C9—C101.4743 (19)C8—H80.9300
C10—C111.4917 (16)C9—H90.9300
C11—C121.3901 (19)C12—H120.9300
C11—C161.3904 (18)C13—H130.9300
C12—C131.3828 (17)C15—H150.9300
C13—C141.3909 (18)C16—H160.9300
C14—C151.3948 (18)C18—H180.9300
C14—C171.4847 (16)C19—H190.9300
C15—C161.3809 (16)C20—H200.9300
C17—C181.3900 (19)C21—H210.9300
C17—C221.384 (2)C22—H220.9300
C18—C191.3840 (18)
C1—C2—C3120.06 (11)C2—C1—H1C109.00
C1—C2—C7121.73 (11)H1A—C1—H1B109.00
C3—C2—C7118.16 (12)H1A—C1—H1C109.00
C2—C3—C4122.16 (12)H1B—C1—H1C109.00
C3—C4—C5119.78 (14)C2—C3—H3119.00
C4—C5—C6119.30 (15)C4—C3—H3119.00
C5—C6—C7121.79 (13)C3—C4—H4120.00
C2—C7—C6118.80 (12)C5—C4—H4120.00
C2—C7—C8120.48 (12)C4—C5—H5120.00
C6—C7—C8120.72 (11)C6—C5—H5120.00
C7—C8—C9126.52 (13)C5—C6—H6119.00
C8—C9—C10122.06 (13)C7—C6—H6119.00
O1—C10—C9121.45 (11)C7—C8—H8117.00
O1—C10—C11119.84 (12)C9—C8—H8117.00
C9—C10—C11118.70 (12)C8—C9—H9119.00
C10—C11—C12122.41 (11)C10—C9—H9119.00
C10—C11—C16118.91 (11)C11—C12—H12120.00
C12—C11—C16118.59 (11)C13—C12—H12120.00
C11—C12—C13120.66 (12)C12—C13—H13119.00
C12—C13—C14121.08 (13)C14—C13—H13119.00
C13—C14—C15117.89 (11)C14—C15—H15119.00
C13—C14—C17120.99 (12)C16—C15—H15119.00
C15—C14—C17121.12 (11)C11—C16—H16120.00
C14—C15—C16121.17 (12)C15—C16—H16120.00
C11—C16—C15120.55 (12)C17—C18—H18120.00
C14—C17—C18120.50 (12)C19—C18—H18120.00
C14—C17—C22121.33 (12)C18—C19—H19120.00
C18—C17—C22118.16 (11)C20—C19—H19120.00
C17—C18—C19120.97 (14)C19—C20—H20120.00
C18—C19—C20120.12 (14)C21—C20—H20120.00
C19—C20—C21119.72 (13)C20—C21—H21120.00
C20—C21—C22120.46 (17)C22—C21—H21120.00
C17—C22—C21120.57 (15)C17—C22—H22120.00
C2—C1—H1A109.00C21—C22—H22120.00
C2—C1—H1B109.00
C1—C2—C3—C4−178.74 (14)C16—C11—C12—C13−1.5 (2)
C7—C2—C3—C4−1.1 (2)C10—C11—C16—C15−176.84 (13)
C1—C2—C7—C6177.97 (13)C12—C11—C16—C15−0.2 (2)
C1—C2—C7—C8−2.3 (2)C11—C12—C13—C141.5 (2)
C3—C2—C7—C60.4 (2)C12—C13—C14—C150.3 (2)
C3—C2—C7—C8−179.93 (14)C12—C13—C14—C17−179.94 (14)
C2—C3—C4—C51.1 (2)C13—C14—C15—C16−2.0 (2)
C3—C4—C5—C6−0.3 (2)C17—C14—C15—C16178.22 (13)
C4—C5—C6—C7−0.4 (2)C13—C14—C17—C1840.6 (2)
C5—C6—C7—C20.4 (2)C13—C14—C17—C22−140.18 (15)
C5—C6—C7—C8−179.34 (14)C15—C14—C17—C18−139.63 (15)
C2—C7—C8—C9161.41 (14)C15—C14—C17—C2239.6 (2)
C6—C7—C8—C9−18.9 (2)C14—C15—C16—C112.0 (2)
C7—C8—C9—C10178.77 (13)C14—C17—C18—C19179.54 (14)
C8—C9—C10—O113.9 (2)C22—C17—C18—C190.3 (2)
C8—C9—C10—C11−164.91 (13)C14—C17—C22—C21−179.96 (16)
O1—C10—C11—C12−158.73 (15)C18—C17—C22—C21−0.7 (2)
O1—C10—C11—C1617.8 (2)C17—C18—C19—C20−0.1 (2)
C9—C10—C11—C1220.1 (2)C18—C19—C20—C210.4 (3)
C9—C10—C11—C16−163.39 (13)C19—C20—C21—C22−0.8 (3)
C10—C11—C12—C13175.01 (14)C20—C21—C22—C171.0 (3)
D—H···AD—HH···AD···AD—H···A
C1—H1C···Cg2i0.962.973.6689 (17)131
C5—H5···Cg3ii0.932.843.5126 (18)130
C21—H21···Cg1iii0.932.993.632 (2)127
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C2–C7 methyl­benzene, C11–C16 benzene and C17–C22 phenyl rings, respectively.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1C⋯Cg2i 0.962.973.6689 (17)131
C5—H5⋯Cg3ii 0.932.843.5126 (18)130
C21—H21⋯Cg1iii 0.932.993.632 (2)127

Symmetry codes: (i) ; (ii) ; (iii) .

  6 in total

1.  A short history of SHELX.

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

Review 2.  [Chalcones and their heterocyclic analogs as potential antifungal chemotherapeutic agents].

Authors:  V Opletalová; D Sedivý
Journal:  Ceska Slov Farm       Date:  1999-11

Review 3.  [Chalcones and their heterocyclic analogs as potential therapeutic agents in bacterial diseases].

Authors:  V Opletalová
Journal:  Ceska Slov Farm       Date:  2000-11

4.  (E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(4-nitro-phen-yl)prop-2-en-1-one.

Authors:  Richard Betz; Thomas Gerber; Eric Hosten; S Samshuddin; Badiadka Narayana; Hemmige S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-05

5.  (2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(4-fluoro-phen-yl)prop-2-en-1-one.

Authors:  Richard Betz; Thomas Gerber; Eric Hosten; S Samshuddin; Badiadka Narayana; Balladka K Sarojini
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-22

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  3 in total

1.  Crystal structure of (E)-1-([1,1'-biphen-yl]-4-yl)-3-(3-nitro-phen-yl)prop-2-en-1-one.

Authors:  D Shanthi; T Vidhyasagar; K Rajeswari; M Kayalvizhi; G Vasuki; A Thiruvalluvar
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-17

2.  Crystal structure of (E)-1-(4'-meth-oxy-[1,1'-biphen-yl]-4-yl)-3-(3-nitro-phen-yl)prop-2-en-1-one.

Authors:  T Vidhyasagar; K Rajeswari; D Shanthi; M Kayalvizhi; G Vasuki; A Thiruvalluvar
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-01

3.  Crystal structure of (E)-1-(4'-methyl-[1,1'-biphen-yl]-4-yl)-3-(3-nitro-phen-yl)prop-2-en-1-one.

Authors:  T Vidhyasagar; K Rajeswari; D Shanthi; M Kayalvizhi; G Vasuki; A Thiruvalluvar
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-01
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.