organic papers
Acta Cryst.(2007). E63, o1353–o1354 doi:10.1107/S1600536807006903 Fischeret al. C
21H15ClO
o1353
Acta Crystallographica Section EStructure Reports Online
ISSN 1600-5368
(2
E
)-3-(Biphenyl-4-yl)-1-(4-chlorophenyl)-prop-2-en-1-one
Andreas Fischer,a* H. S. Yathirajan,bB. V. Ashalatha,c B. Narayanacand B. K. Sarojinid
aInorganic Chemistry, School of Chemical
Science and Engineering, Royal Institute of Technology (KTH), 100 44 Stockholm, Sweden,
bDepartment of Studies in Chemistry, University
of Mysore, Manasagangotri, Mysore 570 006, India,cDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India, anddDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 296 K
Mean(C–C) = 0.008 A˚
Rfactor = 0.067
wRfactor = 0.160
Data-to-parameter ratio = 13.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 30 January 2007 Accepted 9 February 2007
#2007 International Union of Crystallography All rights reserved
The title compound, C21H15ClO, was prepared from biphenyl-4-carbaldehyde and 4-chloroacetophenone. Single crystals were obtained from acetone. The compound is isostructural with the corresponding Br compound. The molecule deviates significantly from planarity.
Comment
For an introduction, see Fischeret al.(2007a).
[image:1.610.223.429.278.388.2]The title chalcone, (I), was prepared by treating 4-chloro-acetophenone with biphenyl-4-carbaldehyde in the presence of KOH.
Fig. 1 shows the molecular structure. The geometry of the molecule is unexceptional; its geometry deviates significantly from planarity [dihedral angles 4.42 (16)within the biphenyl
group and 48.85 (16) between the C10–C15 ring and the
chlorophenyl ring].
The compound is isostructural with the corresponding bromo compound (Fischeret al., 2007b).
Experimental
4-Chloroacetophenone (1.54 g, 0.01 mol) in methanol (20 ml) was mixed with biphenyl-4-carbaldehyde (1.82 g, 0.01 mol) and the
Figure 1
[image:1.610.208.459.592.723.2]mixture was treated with a 30% potassium hydroxide solution (3 ml) at 278 K. The reaction mixture was then brought to room tempera-ture and stirred for 3 h. The precipitated solid was filtered off, washed with water, dried and recrytallized from acetone (m.p. 439–441 K). Analysis (%) for C21H15ClO found (calculated): C 76.83 (76.94), H
4.86 (4.92).
Crystal data
C21H15ClO
Mr= 318.78
Monoclinic,Cc a= 36.723 (14) A˚
b= 7.303 (3) A˚
c= 6.0172 (16) A˚
= 93.06 (3)
V= 1611.4 (10) A˚3
Z= 4
MoKradiation
= 0.24 mm 1
T= 296 K
0.580.480.04 mm
Data collection
Bruker–Nonius KappaCCD diffractometer
Absorption correction: numerical (Herrendorf & Ba¨rnighausen, 1997)
Tmin= 0.716,Tmax= 0.940
7961 measured reflections 2757 independent reflections 1756 reflections withI> 2(I)
Rint= 0.095
Refinement
R[F2> 2(F2)] = 0.067
wR(F2) = 0.160
S= 1.12 2757 reflections 208 parameters
H-atom parameters constrained
max= 0.20 e A˚ 3 min= 0.16 e A˚ 3
Absolute structure: Flack (1983), 1263 Friedel pairs
Flack parameter: 0.02 (15)
H atoms were placed at calculated positions and refined as riding on the respective carrier atom, with C—H = 0.93 A˚ andUiso(H) =
1.2Ueq(C). The structure appears to exhibit turbostratic disorder,
which could be detected in precession photographs that were
simu-lated from the CCD data. The disorder was accounted for in the data processing withEVALCCD(Duisenberget al., 2003).
Data collection: COLLECT (Nonius, 1999); cell refinement:
DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD
(Duisenberget al., 2003); program(s) used to solve structure:SIR97
(Altomare et al., 1997); program(s) used to refine structure:
SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND
(Brandenburg, 2006); software used to prepare material for publi-cation:publCIF(Westrip, 2007).
One of the authors (BKS) thanks AICTE, Government of India, for financial assistance through the Career Award for Young Teacher’s Scheme, and BVA thanks Mangalore University for permission to carry out the research work. The Swedish Research Council (VR) is acknowledged for providing funding for the single-crystal diffractometer.
References
Altomare, A., Cascarano, C., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Burla, M. C., Polidori, G., Camalli, M. & Spagna, R. (1997).SIR97. University of Bari, Italy.
Brandenburg, K. (2006).DIAMOND. Release 3.1d. Crystal Impact GbR, Bonn, Germany.
Duisenberg, A. J. M. (1992).J. Appl. Cryst.25, 92–96.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst.36, 220–229.
Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007a).Acta Cryst.E63, o1349–o1350.
Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007b).Acta Cryst.E63, o1355–o1356.
Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Herrendorf, W. & Ba¨rnighausen, H. (1997). HABITUS. University of Karlsruhe, Germany.
supporting information
sup-1
Acta Cryst. (2007). E63, o1353–o1354
supporting information
Acta Cryst. (2007). E63, o1353–o1354 [https://doi.org/10.1107/S1600536807006903]
(2
E
)-3-(Biphenyl-4-yl)-1-(4-chlorophenyl)prop-2-en-1-one
Andreas Fischer, H. S. Yathirajan, B. V. Ashalatha, B. Narayana and B. K. Sarojini
(2E)-3-(Biphenyl-4-yl)-1-(4-chlorophenyl)prop-2-en-1-one
Crystal data C21H15ClO
Mr = 318.78 Monoclinic, Cc Hall symbol: C -2yc a = 36.723 (14) Å b = 7.303 (3) Å c = 6.0172 (16) Å β = 93.06 (3)° V = 1611.4 (10) Å3
Z = 4
F(000) = 664 Dx = 1.310 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 29 reflections θ = 5.7–18.7°
µ = 0.24 mm−1
T = 296 K
Block, light yellow 0.58 × 0.48 × 0.04 mm
Data collection
Bruker–Nonius KappaCCD diffractometer
Radiation source: fine-focus sealed tube ω scans
Absorption correction: numerical (Herrendorf & Bärnighausen, 1997) Tmin = 0.716, Tmax = 0.940
7961 measured reflections
2757 independent reflections 1756 reflections with I > 2σ(I) Rint = 0.095
θmax = 25.5°, θmin = 4.6°
h = −44→44 k = −8→8 l = −6→7
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.067
wR(F2) = 0.160
S = 1.12 2757 reflections 208 parameters 2 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0352P)2 + 2.1096P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.20 e Å−3
Δρmin = −0.16 e Å−3
Absolute structure: Flack (1983), 1263 Friedel pairs
Absolute structure parameter: 0.02 (15)
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 0.30648 (15) 0.2256 (8) 0.6396 (11) 0.0602 (17)
C2 0.33613 (15) 0.1727 (8) 0.5371 (9) 0.0590 (16)
C3 0.37036 (15) 0.1949 (7) 0.6430 (8) 0.0530 (14)
C4 0.37399 (15) 0.2676 (8) 0.8559 (9) 0.0506 (15)
C5 0.34259 (15) 0.3237 (8) 0.9585 (10) 0.0553 (16)
C6 0.30894 (16) 0.3047 (9) 0.8512 (11) 0.0616 (17)
C7 0.40964 (16) 0.2842 (8) 0.9778 (10) 0.0550 (16)
C8 0.44363 (16) 0.2834 (8) 0.8573 (9) 0.0535 (15)
C9 0.47540 (17) 0.2398 (8) 0.9515 (9) 0.0509 (14)
C10 0.51115 (15) 0.2411 (7) 0.8628 (8) 0.0420 (13)
C11 0.51800 (15) 0.3167 (8) 0.6555 (9) 0.0493 (15)
C12 0.55247 (14) 0.3205 (8) 0.5774 (8) 0.0441 (15)
C13 0.58248 (16) 0.2450 (7) 0.7007 (8) 0.0390 (12)
C14 0.57561 (14) 0.1737 (7) 0.9075 (9) 0.0470 (14)
C15 0.54085 (15) 0.1712 (7) 0.9865 (9) 0.0486 (14)
C16 0.61991 (14) 0.2492 (7) 0.6190 (8) 0.0418 (14)
C17 0.62741 (15) 0.3322 (7) 0.4175 (8) 0.0484 (15)
C18 0.66244 (15) 0.3376 (8) 0.3489 (10) 0.0568 (16)
C19 0.69082 (16) 0.2598 (9) 0.4671 (10) 0.0607 (16)
C20 0.68392 (16) 0.1692 (8) 0.6644 (10) 0.0621 (17)
C21 0.64918 (14) 0.1669 (8) 0.7360 (9) 0.0517 (15)
Cl1 0.26359 (6) 0.2018 (3) 0.5057 (3) 0.1011 (8)
O1 0.41115 (12) 0.2933 (7) 1.1826 (8) 0.0819 (14)
H2 0.3338 0.1215 0.3955 0.071*
H3 0.3910 0.1606 0.5705 0.064*
H5 0.3446 0.3742 1.1005 0.066*
H6 0.2881 0.3439 0.9182 0.074*
H8 0.4424 0.3153 0.7075 0.064*
H9 0.4749 0.2020 1.0989 0.061*
H11 0.4987 0.3656 0.5683 0.059*
H12 0.5560 0.3741 0.4400 0.053*
H14 0.5949 0.1261 0.9960 0.056*
H15 0.5374 0.1213 1.1260 0.058*
H17 0.6086 0.3841 0.3293 0.058*
H18 0.6669 0.3969 0.2163 0.068*
H19 0.7143 0.2666 0.4178 0.073*
H20 0.7027 0.1111 0.7465 0.075*
supporting information
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Acta Cryst. (2007). E63, o1353–o1354
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.055 (4) 0.049 (4) 0.077 (5) 0.000 (3) 0.005 (3) 0.016 (3)
C2 0.067 (4) 0.062 (4) 0.049 (4) −0.001 (3) 0.009 (3) −0.003 (3)
C3 0.063 (3) 0.051 (3) 0.047 (4) 0.002 (3) 0.016 (3) 0.000 (3)
C4 0.052 (3) 0.048 (3) 0.053 (4) 0.000 (3) 0.015 (3) 0.006 (3)
C5 0.058 (4) 0.056 (4) 0.052 (4) −0.001 (3) 0.008 (3) −0.002 (3)
C6 0.049 (3) 0.060 (4) 0.078 (5) 0.004 (3) 0.018 (3) −0.002 (3)
C7 0.063 (4) 0.058 (4) 0.046 (4) 0.003 (3) 0.013 (3) 0.004 (3)
C8 0.055 (4) 0.059 (4) 0.047 (3) 0.004 (3) 0.008 (3) 0.002 (3)
C9 0.058 (3) 0.051 (3) 0.045 (3) −0.002 (3) 0.006 (3) 0.003 (3)
C10 0.051 (3) 0.034 (3) 0.041 (3) −0.001 (2) 0.001 (3) −0.004 (3)
C11 0.049 (3) 0.055 (4) 0.044 (4) 0.004 (3) 0.000 (3) 0.010 (3)
C12 0.050 (3) 0.046 (4) 0.037 (4) 0.001 (3) 0.005 (3) 0.010 (2)
C13 0.054 (3) 0.029 (2) 0.034 (3) 0.001 (2) −0.001 (2) 0.001 (2)
C14 0.052 (3) 0.043 (3) 0.044 (3) 0.006 (3) −0.008 (2) −0.004 (3)
C15 0.063 (4) 0.045 (3) 0.038 (3) −0.001 (3) 0.000 (3) 0.000 (3)
C16 0.051 (4) 0.027 (3) 0.046 (3) −0.004 (2) −0.009 (3) −0.012 (2)
C17 0.066 (4) 0.042 (3) 0.037 (3) 0.006 (3) 0.002 (3) 0.012 (3)
C18 0.058 (3) 0.050 (4) 0.064 (4) 0.004 (3) 0.015 (3) 0.005 (3)
C19 0.054 (3) 0.059 (4) 0.070 (4) 0.002 (3) 0.013 (3) −0.008 (3)
C20 0.051 (4) 0.066 (4) 0.069 (4) 0.002 (3) −0.001 (3) 0.003 (3)
C21 0.058 (4) 0.048 (4) 0.048 (4) −0.001 (3) −0.007 (3) 0.005 (3)
Cl1 0.0693 (10) 0.1388 (19) 0.0934 (14) −0.0007 (14) −0.0132 (9) −0.0046 (15)
O1 0.072 (3) 0.123 (4) 0.052 (3) −0.007 (3) 0.014 (2) −0.008 (3)
Geometric parameters (Å, º)
C1—C2 1.337 (8) C16—C17 1.396 (7)
C1—C6 1.396 (8) C17—C18 1.372 (7)
C1—Cl1 1.739 (6) C18—C19 1.355 (8)
C2—C3 1.388 (7) C19—C20 1.393 (8)
C3—C4 1.387 (7) C20—C21 1.368 (8)
C4—C5 1.398 (8) C2—H2 0.9300
C4—C7 1.471 (8) C3—H3 0.9300
C5—C6 1.370 (8) C5—H5 0.9300
C7—O1 1.232 (7) C6—H6 0.9300
C7—C8 1.477 (8) C8—H8 0.9300
C8—C9 1.309 (8) C9—H9 0.9300
C9—C10 1.444 (9) C11—H11 0.9300
C10—C15 1.385 (8) C12—H12 0.9300
C10—C11 1.398 (7) C14—H14 0.9300
C11—C12 1.374 (8) C15—H15 0.9300
C12—C13 1.408 (8) C17—H17 0.9300
C13—C14 1.384 (7) C18—H18 0.9300
C13—C16 1.485 (7) C19—H19 0.9300
C16—C21 1.389 (7) C21—H21 0.9300
C2—C1—C6 121.7 (5) C20—C21—C16 123.0 (5)
C2—C1—Cl1 119.8 (5) C1—C2—H2 120.2
C6—C1—Cl1 118.5 (4) C3—C2—H2 120.2
C1—C2—C3 119.6 (6) C4—C3—H3 119.7
C4—C3—C2 120.6 (5) C2—C3—H3 119.7
C3—C4—C5 118.6 (5) C6—C5—H5 119.8
C3—C4—C7 122.1 (5) C4—C5—H5 119.8
C5—C4—C7 119.3 (5) C5—C6—H6 120.5
C6—C5—C4 120.4 (6) C1—C6—H6 120.5
C5—C6—C1 118.9 (5) C9—C8—H8 118.5
O1—C7—C4 119.6 (5) C7—C8—H8 118.5
O1—C7—C8 119.8 (6) C8—C9—H9 114.9
C4—C7—C8 120.5 (5) C10—C9—H9 114.9
C9—C8—C7 123.1 (5) C12—C11—H11 119.1
C8—C9—C10 130.2 (6) C10—C11—H11 119.1
C15—C10—C11 116.8 (5) C11—C12—H12 119.3
C15—C10—C9 120.3 (5) C13—C12—H12 119.3
C11—C10—C9 122.9 (5) C13—C14—H14 119.0
C12—C11—C10 121.7 (4) C15—C14—H14 119.0
C11—C12—C13 121.4 (5) C10—C15—H15 119.2
C14—C13—C12 116.5 (5) C14—C15—H15 119.2
C14—C13—C16 121.5 (5) C18—C17—H17 119.8
C12—C13—C16 122.0 (5) C16—C17—H17 119.8
C13—C14—C15 121.9 (5) C19—C18—H18 118.8
C10—C15—C14 121.6 (5) C17—C18—H18 118.8
C21—C16—C17 116.4 (5) C18—C19—H19 120.8
C21—C16—C13 121.9 (5) C20—C19—H19 120.8
C17—C16—C13 121.7 (4) C21—C20—H20 120.4
C18—C17—C16 120.4 (5) C19—C20—H20 120.4
C19—C18—C17 122.5 (6) C20—C21—H21 118.5
C18—C19—C20 118.5 (6) C16—C21—H21 118.5
