organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-3-[4-(Pent­yl­oxy)phen­yl]-1-phenyl­prop-2-en-1-one

aDepartment of Chemistry, Quaid-i-Azam University Islamabad, 45320-Pakistan, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: flavonoids@hotmail.com

(Received 28 April 2009; accepted 4 May 2009; online 14 May 2009)

The title compound, C20H22O2, crystallizes with two independent mol­ecules in the asymmetric unit. In each mol­ecule, all the non-H atoms lie in a common plane (r.m.s. deviations of 0.098 and 0.079 Å). There is a ππ stacking inter­action in the crystal structure. The central aromatic rings of the two mol­ecules, which are stacked head-to-tail one above the other, are separated by centroid-to-centroid distances of 3.872 (13) and 3.999 (10) Å.

Related literature

For background information on chalcones and their properties, see: Achanta et al. (2006[Achanta, G., Modzelewska, A., Feng, L., Khan, S. R. & Huang, P. (2006). Mol. Pharmacol. 70, 426-433.]); Zhang et al. (2009[Zhang, X. D., Hu, X., Hou, A. J. & Wang, H. Y. (2009). Biol. Pharm. Bull. 32, 86-90.]); Tran et al. (2009[Tran, T. D., Park, H., Kim, H. P., Ecker, G. F. & Thai, K. M. (2009). Bioorg. Med. Chem. Lett. 19, 1650-1653.]); Yagura et al. (2008[Yagura, T., Motomiya, T., Ito, M., Honda, G., Iida, A., Kiuchi, F., Tokuda, H. & Nishino, H. (2008). J. Nat. Med. 62, 174-178.]); Sarissky et al. (2008[Sarissky, M., Pilatova, M., Perjesi, P., Mojzis, J. & Sulla, I. (2008). Neuro Oncology. 10, 1112-1112.]); Tang et al. (2008[Tang, Y. X., Simoneau, A. R., Xie, J., Shahandeh, B. & Zi, X. L. (2008). Cancer Prevent. Res. 1, 439-451.]); Srivastava et al. (2008[Srivastava, S. S., Joshi, S., Singh, A. R., Yadav, S., Saxena, A. S., Ram, V. J., Chandra, S. & Saxena, J. K. (2008). Med. Chem. Res. 17, 234-244.]); For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2. pp. S1-19.]). For related structures, see: Rosli et al. (2006[Rosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1466-o1468.]); Harrison et al. (2006[Harrison, W. T. A., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj, K. K. (2006). Acta Cryst. E62, o1578-o1579.]). For the synthesis, see: Wattanasin & Murphy (1980[Wattanasin, S. & Murphy, W. S. (1980). Synthesis, 647-650.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22O2

  • Mr = 294.38

  • Monoclinic, P 21 /c

  • a = 7.4881 (4) Å

  • b = 21.3067 (11) Å

  • c = 20.8328 (11) Å

  • β = 93.974 (4)°

  • V = 3315.8 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 173 K

  • 0.38 × 0.22 × 0.22 mm

Data collection
  • Stoe IPDS II two-circle-diffractometer

  • Absorption correction: none

  • 25934 measured reflections

  • 5819 independent reflections

  • 3319 reflections with I > 2σ(I)

  • Rint = 0.086

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.101

  • S = 0.82

  • 5819 reflections

  • 398 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Selected torsion angles (°)

C11—C1—C2—C3 −177.21 (17)
C2—C1—C11—C12 −13.4 (3)
C2—C1—C11—C16 167.85 (17)
C11A—C1A—C2A—C3A −170.05 (18)
C2A—C1A—C11A—C12A −9.5 (3)
C2A—C1A—C11A—C16A 171.52 (17)

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Benzylideneacetophenones (α, β-Unsaturated ketones) comprise a class of synthetic and naturally occurring compounds belonging to the flavonoid family of compounds, commonly known as "chalcones". Chalcones and their derivatives are used as precursors for the synthesis of a variety of bioactive organic compounds including heterocyclic compounds. Chalcone analogues have been reported to exhibits potent anticancer activity through inhibition of the proteasome (Achanta et al., 2006), tyrosinase (Zhang et al., 2009) and prostaglandin E-2 (Tran et al., 2009). Naringenin chalcone, the aglycone of isosalipurposide (Yagura et al., 2008) have strong anti-proliferative activity. Some synthetic (Sarissky et al., 2008) and naturally occurring chalcones (Tang et al., 2008) have shown good anticancer activity against Ben-Men-1 human benign meningioma cell line and bladder cancer. Oxygenated chalcones and bischalcones (Srivastava et al.,2008) are a new class of inhibitors of DNA topoisomerase-II of malarial parasites. Here, we report on the crystal structure of the title compound, which was prepared and used as a precursor for the synthesis of heterocyclic compounds.

The molecular structue of the title compound is shown in Fig. 1. The geometrical parameters are normal (Allen et al., 1987) and consistent with those of recently reported chalcone derivatives (Rosli et al., 2006). The asymmetric unit consists of two independent conformers distinctly twisted about the C11—C1 / C11A—C1A and the C1—C2 / C1A—C2A bonds (Table 1), as was also observed for 2-bromo-1-chlorophenyl-3-(4-methoxyphenyl)-2-propen-1-one (Harrison et al., 2006). The dihedral angle between the benzene ring mean planes (C11–C16) and (C21–C26), and (C11A–C16A) and (C21A–C26A) are 12.33 (4) and 7.63 (2)°, respectively. Atoms C1 and O1 deviate from the mean plane (C11–C16) by 0.035 (3) and 0.291 (3) Å, respectively. While atoms C1A and O1A deviated from the mean plane (C11A–C16A) by 0.033 (3) and 0.209 (3) Å, respectively.

In the crystal structure of the title compound the two independent molecules stack head-to-tail (Fig. 2). The central aromatic rings of the two molecules are separated by centroid-to-centroid distances of ca. 3.872 and 3.999 Å.

Related literature top

For background information on chalcones and their properties, see: Achanta et al. (2006); Zhang et al. (2009); Tran et al. (2009); Yagura et al. (2008); Sarissky et al. (2008); Tang et al. (2008); Srivastava et al. (2008); For bond-length data, see: Allen et al. (1987). For related structures, see: Rosli et al. (2006); Harrison et al. (2006). For the synthesis, see: Wattanasin & Murphy (1980).

Experimental top

The title compound was synthesized by base catalyzed Claisen–Schmidt condensation reaction (Wattanasin et al., 1980). A mixture of acetophenone (1.20 g, 0.01 mol) and 4-(pentyloxy)benzaldehyde (1.92 g, 0.01 mol) was dissolved in ethanol (50 ml) and then 20 ml of an aqueous solution of potassium hydroxide (5%) was added. The mixture was stirred for 3–4 hr, neutralized with dilute HCl and left to stand for 12 hr. The resulting crude solid mass was collected by filtration and recrystallized from ethanol, yielding crystals of the title compound. Full spectroscopic and physical characterization will be reported elsewhere.

Refinement top

Hydrogen atoms were located in a difference Fourier map but the were included in calculated positions [C-H = 0.95 - 0.99 Å] and refined as riding [Uiso(H) = 1.2 or 1.5Ueq(parent C-atom)]

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. a. Molecular structure of molecule A of the title compound in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. b. Molecular structure of the molecule B of the title compound in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. Crystal packing of the title compound with the π-π-stacking interactions shown as dashed lines. The hydrogen atoms have been removed for clarity.
(E)-3-[4-(pentyloxy)phenyl]-1-phenylprop-2-en-1-one top
Crystal data top
C20H22O2F(000) = 1264
Mr = 294.38Dx = 1.179 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10828 reflections
a = 7.4881 (4) Åθ = 2.2–25.4°
b = 21.3067 (11) ŵ = 0.07 mm1
c = 20.8328 (11) ÅT = 173 K
β = 93.974 (4)°Needle, light yellow
V = 3315.8 (3) Å30.38 × 0.22 × 0.22 mm
Z = 8
Data collection top
STOE IPDS II two-circle-
diffractometer
3319 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.086
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω scansh = 88
25934 measured reflectionsk = 2525
5819 independent reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0461P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max < 0.001
5819 reflectionsΔρmax = 0.15 e Å3
398 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0076 (8)
Crystal data top
C20H22O2V = 3315.8 (3) Å3
Mr = 294.38Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.4881 (4) ŵ = 0.07 mm1
b = 21.3067 (11) ÅT = 173 K
c = 20.8328 (11) Å0.38 × 0.22 × 0.22 mm
β = 93.974 (4)°
Data collection top
STOE IPDS II two-circle-
diffractometer
3319 reflections with I > 2σ(I)
25934 measured reflectionsRint = 0.086
5819 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 0.82Δρmax = 0.15 e Å3
5819 reflectionsΔρmin = 0.19 e Å3
398 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3753 (2)0.28357 (6)0.50789 (6)0.0563 (4)
O20.36921 (18)0.62946 (6)0.31330 (6)0.0438 (3)
C10.4030 (2)0.27970 (9)0.45038 (8)0.0374 (4)
C20.4045 (2)0.33580 (9)0.40938 (8)0.0377 (4)
H20.41990.33140.36470.045*
C30.3843 (2)0.39303 (9)0.43424 (9)0.0391 (4)
H30.36950.39430.47910.047*
C40.3530 (3)0.68540 (8)0.35105 (8)0.0404 (5)
H4A0.45670.68910.38300.049*
H4B0.24250.68360.37450.049*
C50.3465 (3)0.74114 (9)0.30660 (8)0.0410 (5)
H5A0.23750.73870.27690.049*
H5B0.45190.74030.28040.049*
C60.3451 (3)0.80230 (9)0.34415 (8)0.0407 (5)
H6A0.24240.80180.37160.049*
H6B0.45580.80480.37290.049*
C70.3323 (3)0.86063 (9)0.30226 (9)0.0485 (5)
H7A0.42930.85960.27230.058*
H7B0.21680.86000.27610.058*
C80.3457 (3)0.92128 (10)0.34037 (12)0.0625 (6)
H8A0.33720.95700.31070.094*
H8B0.46080.92270.36580.094*
H8C0.24800.92330.36920.094*
C110.4342 (2)0.21639 (9)0.42220 (8)0.0344 (4)
C120.4295 (2)0.20512 (9)0.35622 (8)0.0400 (4)
H120.40780.23880.32690.048*
C130.4562 (3)0.14507 (9)0.33307 (9)0.0481 (5)
H130.45410.13790.28800.058*
C140.4859 (3)0.09584 (10)0.37528 (10)0.0527 (5)
H140.50210.05460.35930.063*
C150.4920 (3)0.10636 (10)0.44094 (10)0.0544 (6)
H150.51400.07250.47010.065*
C160.4661 (3)0.16618 (9)0.46385 (9)0.0463 (5)
H160.47010.17310.50900.056*
C210.3818 (2)0.45381 (9)0.40194 (8)0.0366 (4)
C220.4064 (2)0.46178 (9)0.33614 (8)0.0419 (5)
H220.42640.42610.31030.050*
C230.4021 (3)0.52028 (9)0.30860 (9)0.0438 (5)
H230.41900.52460.26400.053*
C240.3730 (2)0.57350 (9)0.34540 (8)0.0373 (4)
C250.3491 (3)0.56698 (9)0.41056 (8)0.0422 (5)
H250.33080.60290.43630.051*
C260.3522 (3)0.50777 (9)0.43742 (9)0.0431 (5)
H260.33340.50360.48180.052*
O1A0.8034 (2)0.81245 (6)0.24815 (6)0.0549 (4)
O2A0.90510 (18)0.45190 (6)0.41506 (5)0.0432 (3)
C1A0.8272 (2)0.80873 (9)0.30728 (8)0.0386 (4)
C2A0.8414 (2)0.74769 (9)0.33972 (8)0.0383 (4)
H2A0.84140.74640.38530.046*
C3A0.8545 (2)0.69393 (9)0.30771 (8)0.0386 (4)
H3A0.85360.69690.26220.046*
C4A0.9039 (3)0.39658 (8)0.37602 (8)0.0407 (4)
H4A11.00810.39670.34930.049*
H4A20.79330.39510.34710.049*
C5A0.9124 (3)0.34046 (9)0.42018 (9)0.0422 (5)
H5A10.80570.34020.44570.051*
H5A21.01980.34380.45050.051*
C6A0.9201 (3)0.27920 (8)0.38292 (9)0.0448 (5)
H6A10.81040.27550.35380.054*
H6A21.02370.28060.35590.054*
C7A0.9362 (3)0.22144 (10)0.42529 (11)0.0575 (6)
H7A10.82920.21850.45050.069*
H7A21.04240.22590.45600.069*
C8A0.9535 (3)0.16114 (10)0.38681 (14)0.0798 (8)
H8A10.96300.12530.41630.120*
H8A21.06090.16330.36260.120*
H8A30.84770.15610.35680.120*
C11A0.8432 (2)0.86778 (9)0.34646 (8)0.0364 (4)
C12A0.8455 (3)0.86841 (9)0.41317 (8)0.0441 (5)
H12A0.84040.83000.43610.053*
C13A0.8553 (3)0.92462 (10)0.44644 (10)0.0533 (5)
H13A0.85480.92460.49200.064*
C14A0.8656 (3)0.98053 (10)0.41389 (10)0.0525 (5)
H14A0.87251.01900.43700.063*
C15A0.8661 (3)0.98060 (9)0.34781 (10)0.0512 (5)
H15A0.87511.01920.32540.061*
C16A0.8533 (3)0.92468 (9)0.31398 (9)0.0437 (5)
H16A0.85140.92510.26830.052*
C21A0.8699 (2)0.63097 (9)0.33500 (8)0.0367 (4)
C22A0.8770 (3)0.62003 (9)0.40134 (8)0.0412 (5)
H22A0.87150.65460.42990.049*
C23A0.8918 (3)0.56028 (9)0.42609 (9)0.0431 (5)
H23A0.89940.55420.47140.052*
C24A0.8957 (2)0.50891 (8)0.38534 (8)0.0361 (4)
C25A0.8902 (2)0.51804 (9)0.31898 (8)0.0405 (5)
H25A0.89430.48330.29060.049*
C26A0.8787 (3)0.57867 (9)0.29517 (8)0.0420 (5)
H26A0.87660.58490.25000.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0865 (11)0.0481 (9)0.0348 (7)0.0088 (8)0.0074 (7)0.0041 (6)
O20.0578 (8)0.0340 (8)0.0403 (7)0.0030 (6)0.0070 (6)0.0019 (6)
C10.0362 (10)0.0384 (11)0.0372 (10)0.0006 (8)0.0002 (8)0.0023 (8)
C20.0400 (11)0.0369 (11)0.0365 (9)0.0005 (9)0.0039 (8)0.0026 (8)
C30.0373 (10)0.0402 (12)0.0398 (10)0.0013 (9)0.0016 (8)0.0026 (8)
C40.0469 (11)0.0327 (11)0.0419 (10)0.0040 (9)0.0052 (8)0.0031 (8)
C50.0434 (11)0.0382 (11)0.0415 (10)0.0026 (9)0.0034 (8)0.0014 (8)
C60.0416 (11)0.0379 (11)0.0428 (10)0.0014 (9)0.0033 (8)0.0011 (8)
C70.0478 (12)0.0419 (12)0.0556 (12)0.0010 (10)0.0019 (9)0.0054 (9)
C80.0582 (14)0.0398 (13)0.0881 (16)0.0016 (11)0.0051 (12)0.0027 (12)
C110.0310 (9)0.0323 (10)0.0401 (9)0.0001 (8)0.0037 (7)0.0001 (8)
C120.0456 (11)0.0365 (11)0.0380 (9)0.0028 (9)0.0036 (8)0.0008 (8)
C130.0592 (13)0.0392 (12)0.0470 (11)0.0030 (10)0.0114 (9)0.0082 (9)
C140.0604 (14)0.0357 (12)0.0638 (13)0.0038 (10)0.0168 (10)0.0028 (10)
C150.0715 (15)0.0389 (12)0.0540 (12)0.0060 (11)0.0131 (11)0.0108 (10)
C160.0553 (12)0.0422 (12)0.0425 (10)0.0025 (10)0.0104 (9)0.0017 (9)
C210.0343 (10)0.0344 (11)0.0409 (10)0.0019 (8)0.0031 (8)0.0026 (8)
C220.0464 (11)0.0390 (12)0.0410 (10)0.0002 (9)0.0079 (8)0.0077 (9)
C230.0549 (12)0.0406 (12)0.0369 (10)0.0022 (10)0.0099 (9)0.0036 (9)
C240.0380 (10)0.0343 (11)0.0400 (10)0.0042 (8)0.0046 (8)0.0012 (8)
C250.0527 (12)0.0341 (11)0.0405 (10)0.0031 (9)0.0080 (8)0.0071 (8)
C260.0545 (12)0.0387 (12)0.0368 (10)0.0040 (10)0.0077 (9)0.0038 (8)
O1A0.0860 (11)0.0418 (8)0.0360 (7)0.0002 (8)0.0008 (7)0.0018 (6)
O2A0.0588 (9)0.0313 (8)0.0397 (7)0.0033 (6)0.0043 (6)0.0012 (6)
C1A0.0390 (11)0.0364 (11)0.0404 (10)0.0007 (9)0.0022 (8)0.0015 (8)
C2A0.0435 (11)0.0351 (11)0.0364 (9)0.0001 (9)0.0035 (8)0.0001 (8)
C3A0.0416 (11)0.0381 (11)0.0360 (9)0.0008 (9)0.0015 (8)0.0020 (8)
C4A0.0464 (11)0.0333 (11)0.0418 (10)0.0007 (9)0.0011 (8)0.0022 (8)
C5A0.0406 (11)0.0402 (12)0.0460 (11)0.0001 (9)0.0042 (8)0.0038 (9)
C6A0.0455 (11)0.0323 (11)0.0557 (11)0.0029 (9)0.0018 (9)0.0051 (9)
C7A0.0435 (12)0.0408 (13)0.0879 (15)0.0026 (10)0.0012 (11)0.0214 (11)
C8A0.0639 (16)0.0321 (13)0.140 (2)0.0054 (12)0.0151 (15)0.0103 (14)
C11A0.0342 (10)0.0334 (11)0.0416 (10)0.0008 (8)0.0034 (8)0.0013 (8)
C12A0.0568 (13)0.0344 (11)0.0408 (10)0.0011 (10)0.0012 (9)0.0023 (8)
C13A0.0693 (15)0.0438 (13)0.0464 (11)0.0047 (11)0.0003 (10)0.0061 (10)
C14A0.0574 (13)0.0383 (13)0.0618 (14)0.0052 (10)0.0042 (10)0.0089 (10)
C15A0.0555 (13)0.0343 (12)0.0639 (13)0.0018 (10)0.0055 (10)0.0062 (10)
C16A0.0493 (12)0.0364 (11)0.0453 (11)0.0014 (9)0.0035 (9)0.0052 (9)
C21A0.0387 (10)0.0334 (11)0.0381 (10)0.0021 (8)0.0033 (8)0.0004 (8)
C22A0.0544 (12)0.0344 (11)0.0353 (9)0.0040 (9)0.0067 (8)0.0049 (8)
C23A0.0582 (13)0.0377 (12)0.0343 (9)0.0056 (9)0.0098 (8)0.0011 (8)
C24A0.0386 (11)0.0334 (11)0.0364 (10)0.0035 (8)0.0026 (8)0.0016 (8)
C25A0.0498 (12)0.0326 (11)0.0387 (10)0.0029 (9)0.0009 (8)0.0051 (8)
C26A0.0538 (12)0.0390 (12)0.0330 (9)0.0031 (9)0.0025 (8)0.0008 (8)
Geometric parameters (Å, º) top
O1—C11.2326 (19)O1A—C1A1.235 (2)
O2—C241.366 (2)O2A—C24A1.363 (2)
O2—C41.438 (2)O2A—C4A1.432 (2)
C1—C21.470 (3)C1A—C2A1.466 (3)
C1—C111.496 (3)C1A—C11A1.500 (3)
C2—C31.338 (3)C2A—C3A1.332 (2)
C2—H20.9500C2A—H2A0.9500
C3—C211.459 (3)C3A—C21A1.459 (3)
C3—H30.9500C3A—H3A0.9500
C4—C51.505 (2)C4A—C5A1.507 (2)
C4—H4A0.9900C4A—H4A10.9900
C4—H4B0.9900C4A—H4A20.9900
C5—C61.520 (3)C5A—C6A1.522 (3)
C5—H5A0.9900C5A—H5A10.9900
C5—H5B0.9900C5A—H5A20.9900
C6—C71.518 (3)C6A—C7A1.515 (3)
C6—H6A0.9900C6A—H6A10.9900
C6—H6B0.9900C6A—H6A20.9900
C7—C81.516 (3)C7A—C8A1.525 (3)
C7—H7A0.9900C7A—H7A10.9900
C7—H7B0.9900C7A—H7A20.9900
C8—H8A0.9800C8A—H8A10.9800
C8—H8B0.9800C8A—H8A20.9800
C8—H8C0.9800C8A—H8A30.9800
C11—C161.388 (3)C11A—C12A1.389 (2)
C11—C121.393 (2)C11A—C16A1.393 (3)
C12—C131.387 (3)C12A—C13A1.383 (3)
C12—H120.9500C12A—H12A0.9500
C13—C141.377 (3)C13A—C14A1.376 (3)
C13—H130.9500C13A—H13A0.9500
C14—C151.384 (3)C14A—C15A1.377 (3)
C14—H140.9500C14A—H14A0.9500
C15—C161.379 (3)C15A—C16A1.384 (3)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C21—C261.393 (3)C21A—C26A1.394 (3)
C21—C221.406 (2)C21A—C22A1.399 (2)
C22—C231.372 (3)C22A—C23A1.375 (3)
C22—H220.9500C22A—H22A0.9500
C23—C241.394 (3)C23A—C24A1.387 (2)
C23—H230.9500C23A—H23A0.9500
C24—C251.388 (2)C24A—C25A1.394 (2)
C25—C261.380 (3)C25A—C26A1.384 (3)
C25—H250.9500C25A—H25A0.9500
C26—H260.9500C26A—H26A0.9500
C24—O2—C4117.09 (13)C24A—O2A—C4A118.52 (13)
O1—C1—C2121.27 (17)O1A—C1A—C2A121.18 (17)
O1—C1—C11118.89 (16)O1A—C1A—C11A119.30 (17)
C2—C1—C11119.83 (15)C2A—C1A—C11A119.52 (16)
C3—C2—C1120.71 (16)C3A—C2A—C1A122.50 (16)
C3—C2—H2119.6C3A—C2A—H2A118.8
C1—C2—H2119.6C1A—C2A—H2A118.8
C2—C3—C21128.96 (17)C2A—C3A—C21A127.02 (17)
C2—C3—H3115.5C2A—C3A—H3A116.5
C21—C3—H3115.5C21A—C3A—H3A116.5
O2—C4—C5108.55 (14)O2A—C4A—C5A107.93 (14)
O2—C4—H4A110.0O2A—C4A—H4A1110.1
C5—C4—H4A110.0C5A—C4A—H4A1110.1
O2—C4—H4B110.0O2A—C4A—H4A2110.1
C5—C4—H4B110.0C5A—C4A—H4A2110.1
H4A—C4—H4B108.4H4A1—C4A—H4A2108.4
C4—C5—C6111.17 (15)C4A—C5A—C6A111.76 (15)
C4—C5—H5A109.4C4A—C5A—H5A1109.3
C6—C5—H5A109.4C6A—C5A—H5A1109.3
C4—C5—H5B109.4C4A—C5A—H5A2109.3
C6—C5—H5B109.4C6A—C5A—H5A2109.3
H5A—C5—H5B108.0H5A1—C5A—H5A2107.9
C7—C6—C5114.12 (15)C7A—C6A—C5A113.83 (16)
C7—C6—H6A108.7C7A—C6A—H6A1108.8
C5—C6—H6A108.7C5A—C6A—H6A1108.8
C7—C6—H6B108.7C7A—C6A—H6A2108.8
C5—C6—H6B108.7C5A—C6A—H6A2108.8
H6A—C6—H6B107.6H6A1—C6A—H6A2107.7
C8—C7—C6113.43 (17)C6A—C7A—C8A112.62 (19)
C8—C7—H7A108.9C6A—C7A—H7A1109.1
C6—C7—H7A108.9C8A—C7A—H7A1109.1
C8—C7—H7B108.9C6A—C7A—H7A2109.1
C6—C7—H7B108.9C8A—C7A—H7A2109.1
H7A—C7—H7B107.7H7A1—C7A—H7A2107.8
C7—C8—H8A109.5C7A—C8A—H8A1109.5
C7—C8—H8B109.5C7A—C8A—H8A2109.5
H8A—C8—H8B109.5H8A1—C8A—H8A2109.5
C7—C8—H8C109.5C7A—C8A—H8A3109.5
H8A—C8—H8C109.5H8A1—C8A—H8A3109.5
H8B—C8—H8C109.5H8A2—C8A—H8A3109.5
C16—C11—C12118.38 (17)C12A—C11A—C16A118.70 (18)
C16—C11—C1118.33 (15)C12A—C11A—C1A123.21 (17)
C12—C11—C1123.28 (16)C16A—C11A—C1A118.08 (16)
C13—C12—C11120.51 (18)C13A—C12A—C11A120.43 (18)
C13—C12—H12119.7C13A—C12A—H12A119.8
C11—C12—H12119.7C11A—C12A—H12A119.8
C14—C13—C12120.10 (18)C14A—C13A—C12A120.37 (19)
C14—C13—H13119.9C14A—C13A—H13A119.8
C12—C13—H13119.9C12A—C13A—H13A119.8
C13—C14—C15120.05 (19)C13A—C14A—C15A119.9 (2)
C13—C14—H14120.0C13A—C14A—H14A120.1
C15—C14—H14120.0C15A—C14A—H14A120.1
C16—C15—C14119.72 (19)C14A—C15A—C16A120.21 (19)
C16—C15—H15120.1C14A—C15A—H15A119.9
C14—C15—H15120.1C16A—C15A—H15A119.9
C15—C16—C11121.22 (18)C15A—C16A—C11A120.40 (18)
C15—C16—H16119.4C15A—C16A—H16A119.8
C11—C16—H16119.4C11A—C16A—H16A119.8
C26—C21—C22117.01 (17)C26A—C21A—C22A117.06 (17)
C26—C21—C3119.03 (16)C26A—C21A—C3A120.60 (16)
C22—C21—C3123.96 (17)C22A—C21A—C3A122.34 (16)
C23—C22—C21121.11 (17)C23A—C22A—C21A121.41 (17)
C23—C22—H22119.4C23A—C22A—H22A119.3
C21—C22—H22119.4C21A—C22A—H22A119.3
C22—C23—C24120.61 (17)C22A—C23A—C24A120.38 (17)
C22—C23—H23119.7C22A—C23A—H23A119.8
C24—C23—H23119.7C24A—C23A—H23A119.8
O2—C24—C25124.47 (17)O2A—C24A—C23A115.34 (15)
O2—C24—C23116.06 (15)O2A—C24A—C25A124.88 (16)
C25—C24—C23119.47 (18)C23A—C24A—C25A119.78 (17)
C26—C25—C24119.22 (17)C26A—C25A—C24A118.84 (17)
C26—C25—H25120.4C26A—C25A—H25A120.6
C24—C25—H25120.4C24A—C25A—H25A120.6
C25—C26—C21122.57 (17)C25A—C26A—C21A122.49 (17)
C25—C26—H26118.7C25A—C26A—H26A118.8
C21—C26—H26118.7C21A—C26A—H26A118.8
O1—C1—C2—C33.2 (3)O1A—C1A—C2A—C3A9.5 (3)
C11—C1—C2—C3177.21 (17)C11A—C1A—C2A—C3A170.05 (18)
C1—C2—C3—C21179.97 (18)C1A—C2A—C3A—C21A179.74 (18)
C24—O2—C4—C5178.53 (15)C24A—O2A—C4A—C5A179.11 (16)
O2—C4—C5—C6175.23 (15)O2A—C4A—C5A—C6A177.50 (16)
C4—C5—C6—C7178.06 (17)C4A—C5A—C6A—C7A177.72 (17)
C5—C6—C7—C8175.46 (18)C5A—C6A—C7A—C8A176.95 (18)
O1—C1—C11—C1612.6 (3)O1A—C1A—C11A—C12A170.93 (18)
C2—C1—C11—C1213.4 (3)C2A—C1A—C11A—C12A9.5 (3)
C2—C1—C11—C16167.85 (17)O1A—C1A—C11A—C16A8.0 (3)
O1—C1—C11—C12166.19 (17)C2A—C1A—C11A—C16A171.52 (17)
C16—C11—C12—C130.0 (3)C16A—C11A—C12A—C13A0.8 (3)
C1—C11—C12—C13178.79 (18)C1A—C11A—C12A—C13A178.11 (19)
C11—C12—C13—C140.7 (3)C11A—C12A—C13A—C14A1.0 (3)
C12—C13—C14—C151.1 (3)C12A—C13A—C14A—C15A0.1 (3)
C13—C14—C15—C160.8 (3)C13A—C14A—C15A—C16A1.0 (3)
C14—C15—C16—C110.2 (3)C14A—C15A—C16A—C11A1.2 (3)
C12—C11—C16—C150.2 (3)C12A—C11A—C16A—C15A0.3 (3)
C1—C11—C16—C15178.60 (18)C1A—C11A—C16A—C15A179.26 (18)
C2—C3—C21—C26177.7 (2)C2A—C3A—C21A—C26A178.60 (19)
C2—C3—C21—C221.8 (3)C2A—C3A—C21A—C22A1.5 (3)
C26—C21—C22—C230.3 (3)C26A—C21A—C22A—C23A0.1 (3)
C3—C21—C22—C23179.79 (19)C3A—C21A—C22A—C23A179.92 (18)
C21—C22—C23—C240.0 (3)C21A—C22A—C23A—C24A1.6 (3)
C4—O2—C24—C255.0 (3)C4A—O2A—C24A—C23A178.06 (17)
C4—O2—C24—C23175.43 (17)C4A—O2A—C24A—C25A2.0 (3)
C22—C23—C24—O2179.33 (17)C22A—C23A—C24A—O2A178.06 (17)
C22—C23—C24—C250.3 (3)C22A—C23A—C24A—C25A2.0 (3)
O2—C24—C25—C26178.69 (18)O2A—C24A—C25A—C26A179.28 (17)
C23—C24—C25—C260.9 (3)C23A—C24A—C25A—C26A0.8 (3)
C24—C25—C26—C211.2 (3)C24A—C25A—C26A—C21A0.9 (3)
C22—C21—C26—C250.9 (3)C22A—C21A—C26A—C25A1.3 (3)
C3—C21—C26—C25179.55 (18)C3A—C21A—C26A—C25A178.83 (18)

Experimental details

Crystal data
Chemical formulaC20H22O2
Mr294.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)7.4881 (4), 21.3067 (11), 20.8328 (11)
β (°) 93.974 (4)
V3)3315.8 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.38 × 0.22 × 0.22
Data collection
DiffractometerSTOE IPDS II two-circle-
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25934, 5819, 3319
Rint0.086
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.101, 0.82
No. of reflections5819
No. of parameters398
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.19

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Selected torsion angles (º) top
C11—C1—C2—C3177.21 (17)C11A—C1A—C2A—C3A170.05 (18)
C2—C1—C11—C1213.4 (3)C2A—C1A—C11A—C12A9.5 (3)
C2—C1—C11—C16167.85 (17)C2A—C1A—C11A—C16A171.52 (17)
 

Acknowledgements

AA is grateful to the Higher Education Commission of Pakistan for financial support for his PhD program under scholarship No. IIC–0317109.

References

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