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Acta Cryst. (2009). E65, o1281    [ doi:10.1107/S1600536809017358 ]

4-Hexyloxy-3-methoxybenzaldehyde

A. Abbas, M. Khawar Rauf, M. Bolte and A. Hasan

Abstract top

The title compound, C14H20O3, is a synthetic analogue with a long aliphatic side chain of the important food additive and flavoring agent, vanillin. There are two independent molecules in the asymmetric unit, each having an essentially planar conformation (r.m.s. deviations of 0.023 and 0.051Å for all non-H atoms of the two molecules in the asymmetric unit).

Comment top

Vanillin, a well known flavoring agent, is the principal flavor and aroma compound in vanilla. Vanillin and its derivatives have been used as flavoring food additives and precursors for the synthesis of organic compounds, and have been reported to show diverse biological applications. Schiff-base derivatives (Guo et al., 2008), metal complexes (Neelakantan et al., 2008) and 2-amino-4-phenylthiazole derivatives (Ashalekshmi et al., 2008) of vanillin have shown potential antibacterial activities against E. Coli, S. Aureus, B. Subtilis, P. Aeruginosa, K. Pneumoniae, B. Megaterium, V. Cholerae, and S. Typhi,. Bromovanin (6-bromine-5-hydroxy-4-methoxybenzaldehyde) (Yan et al., 2007) and caffeate analogues (Xia et al., 2008) derived from vanillin exhibits a potent anti-proliferative effect on a broad spectrum of cancer cell lines. Vanillin (Liang et al., 2009) and glycosides of vanillin (Charles et al., 2009), exhibit enzyme inhibition, antioxidant, anti-angiogenic, anti-inflammatory and anti-nociceptive activities (Lim et al., 2008). As part of interest in vanillin derivatives, we now report the crystal structure of the title compound (I). A view of compound (I), is shown in Fig 1. The geometrical parameters for (I) are normal (Allen et al.,1987) and consistent with those of recently reported ethyl vanillin structure (Li, 2008).The asymmetric unit consist two conformers, each having almost planar conformation. C8, O1 and O2 deviate from the mean plane (C11–C16) by 0.028 (3), 0.020 (2), and 0.020 (2) A°, respectively. The deviations of C8A, O1A and O2A from the mean plane (C11A–C16A) are 0.001 (3), 0.025 (2) and 0.011 (2) A°, respectively.

Related literature top

For background information, see: Guo et al. (2008); Neelakantan et al. (2008); Ashalekshmi et al. (2008); Yan et al. (2007); Xia et al. (2008); Liang et al. (2009); Charles et al. (2009); Lim et al. (2008); Williamson (1852). For related structures, see: Li (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

Vanillin (4-hydroxy-3-methoxybenzaldehyde) (1.52 g) was dissolved in butan-2-one (20 ml), then added K2CO3 (1.38 g), heated at 60°C and stirred for half an hour. 1-Bromohexane (1.65 g) was added to the reaction mixture and refluxed for 3–4 h on an oil bath (Williamson, 1852). The progress of the reaction was monitored by TLC. Once the reaction was completed, the product was extracted in diethyl ether, solvent evaporated under reduced pressure and crystallized from dichloromethane to get the title compound (I).

Refinement top

Hydrogen atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with Caromatic—H = 0.95 Å, Cmethylene—H = 0.99 Å, Uiso(H) = 1.2U(Ceq) or Cmethyl—H = 0.98 Å. The highest peak in the final difference density map (0.68 e Å-3) is located at 0.76Å from H8A.

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. Molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
4-Hexyloxy-3-methoxybenzaldehyde top
Crystal data top
C14H20O3Z = 4
Mr = 236.30F000 = 512
Triclinic, P1Dx = 1.194 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.2788 (5) ÅCell parameters from 16295 reflections
b = 9.3894 (6) Åθ = 3.5–25.9º
c = 15.8501 (9) ŵ = 0.08 mm−1
α = 88.099 (5)ºT = 173 K
β = 75.065 (5)ºBlock, colourless
γ = 80.262 (5)º0.42 × 0.37 × 0.36 mm
V = 1314.95 (13) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer		3862 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Monochromator: graphiteθmax = 25.6º
T = 173 Kθmin = 3.4º
ω scansh = −11→11
Absorption correction: nonek = −11→11
17943 measured reflectionsl = −19→19
4919 independent reflections
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0794P)2 + 0.213P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4919 reflectionsΔρmax = 0.69 e Å−3
309 parametersΔρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C14H20O3γ = 80.262 (5)º
Mr = 236.30V = 1314.95 (13) Å3
Triclinic, P1Z = 4
a = 9.2788 (5) ÅMo Kα
b = 9.3894 (6) ŵ = 0.08 mm−1
c = 15.8501 (9) ÅT = 173 K
α = 88.099 (5)º0.42 × 0.37 × 0.36 mm
β = 75.065 (5)º
Data collection top
STOE IPDS II two-circle-
diffractometer		4919 independent reflections
Absorption correction: none3862 reflections with I > 2σ(I)
17943 measured reflectionsRint = 0.046
Refinement top
R[F2 > 2σ(F2)] = 0.049309 parameters
wR(F2) = 0.144H-atom parameters constrained
S = 1.06Δρmax = 0.69 e Å−3
4919 reflectionsΔρmin = −0.28 e Å−3
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
O10.65027 (12)0.60519 (12)0.99368 (6)0.0403 (3)
O20.69937 (12)0.56660 (11)1.14584 (6)0.0397 (3)
O31.13475 (16)0.12211 (15)1.10444 (9)0.0648 (4)
C10.62080 (18)0.63144 (18)0.90887 (9)0.0412 (4)
H1A0.58700.54630.88970.049*
H1B0.71460.64750.86560.049*
C20.50012 (17)0.76247 (17)0.91409 (9)0.0395 (4)
H2A0.53420.84790.93270.047*
H2B0.40640.74680.95760.047*
C30.46892 (16)0.78865 (17)0.82439 (9)0.0376 (3)
H3A0.56250.80870.78250.045*
H3B0.44420.69900.80460.045*
C40.34118 (16)0.91241 (17)0.82143 (9)0.0372 (3)
H4A0.24740.89350.86360.045*
H4B0.36641.00290.83980.045*
C50.31230 (17)0.93292 (17)0.73137 (10)0.0399 (4)
H5A0.28740.84230.71290.048*
H5B0.40590.95220.68920.048*
C60.1844 (2)1.05620 (19)0.72871 (12)0.0510 (4)
H6A0.17011.06430.66950.076*
H6B0.20971.14680.74520.076*
H6C0.09101.03710.76970.076*
C70.72298 (18)0.55017 (17)1.23152 (9)0.0405 (4)
H7A0.70670.45371.25320.061*
H7B0.65170.62351.27070.061*
H7C0.82680.56211.22940.061*
C81.0993 (2)0.1514 (2)1.03692 (11)0.0514 (4)
H81.15340.09350.98710.062*
C110.75896 (17)0.49258 (16)0.99937 (9)0.0354 (3)
C120.78770 (16)0.47099 (16)1.08300 (9)0.0338 (3)
C130.89766 (16)0.36073 (16)1.09506 (9)0.0359 (3)
H130.91770.34701.15090.043*
C140.98097 (17)0.26779 (17)1.02520 (10)0.0393 (3)
C150.95082 (18)0.28820 (18)0.94401 (10)0.0433 (4)
H151.00630.22500.89690.052*
C160.84110 (18)0.39934 (17)0.93083 (9)0.0403 (4)
H160.82160.41220.87490.048*
O1A0.54463 (11)0.20255 (12)0.59371 (6)0.0393 (3)
O2A0.57832 (11)0.17700 (11)0.75033 (6)0.0396 (3)
O3A1.10136 (16)−0.29636 (16)0.61496 (10)0.0718 (4)
C1A0.52746 (17)0.22746 (18)0.50646 (9)0.0390 (3)
H1A10.51650.13650.48070.047*
H1A20.61770.26210.46930.047*
C2A0.38839 (16)0.33951 (18)0.51114 (9)0.0384 (3)
H2A10.39690.42740.54110.046*
H2A20.29800.30170.54560.046*
C3A0.36975 (16)0.37813 (18)0.41991 (9)0.0382 (3)
H3A10.45910.41870.38660.046*
H3A20.36660.28880.38940.046*
C4A0.22797 (17)0.48624 (18)0.42019 (9)0.0395 (3)
H4A10.22980.57450.45210.047*
H4A20.13850.44460.45220.047*
C5A0.21109 (17)0.52794 (18)0.32935 (10)0.0415 (4)
H5A10.30060.56930.29700.050*
H5A20.20790.44010.29750.050*
C6A0.06916 (19)0.6370 (2)0.33156 (11)0.0489 (4)
H6A10.06310.66030.27170.073*
H6A20.07280.72510.36180.073*
H6A3−0.02000.59590.36260.073*
C7A0.60438 (19)0.17584 (18)0.83582 (10)0.0449 (4)
H7A10.59740.08000.86140.067*
H7A20.52810.24840.87300.067*
H7A30.70540.19840.83140.067*
C8A1.00578 (19)−0.2192 (2)0.66439 (14)0.0553 (5)
H8A1.0044−0.22730.72450.066*
C11A0.65958 (15)0.09930 (16)0.60415 (10)0.0349 (3)
C12A0.67768 (15)0.08413 (16)0.68992 (9)0.0337 (3)
C13A0.78979 (16)−0.01963 (16)0.70729 (10)0.0380 (3)
H13A0.8014−0.03000.76510.046*
C14A0.88682 (16)−0.11002 (17)0.64056 (11)0.0417 (4)
C15A0.87018 (17)−0.09402 (18)0.55633 (11)0.0464 (4)
H15A0.9365−0.15460.51080.056*
C16A0.75726 (17)0.00993 (18)0.53781 (10)0.0427 (4)
H16A0.74660.02010.47980.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0492 (6)0.0449 (6)0.0270 (5)−0.0025 (5)−0.0137 (4)0.0013 (4)
O20.0483 (6)0.0419 (6)0.0271 (5)0.0031 (4)−0.0126 (4)−0.0041 (4)
O30.0685 (8)0.0662 (9)0.0524 (8)0.0149 (7)−0.0189 (6)0.0002 (6)
C10.0522 (9)0.0488 (9)0.0261 (7)−0.0103 (7)−0.0153 (6)0.0041 (6)
C20.0456 (8)0.0448 (9)0.0309 (8)−0.0121 (7)−0.0124 (6)0.0037 (6)
C30.0382 (7)0.0468 (9)0.0300 (7)−0.0104 (6)−0.0105 (6)0.0027 (6)
C40.0374 (7)0.0426 (9)0.0329 (8)−0.0102 (6)−0.0090 (6)−0.0014 (6)
C50.0394 (7)0.0451 (9)0.0368 (8)−0.0049 (6)−0.0136 (6)−0.0009 (6)
C60.0560 (10)0.0499 (10)0.0481 (10)0.0034 (8)−0.0225 (8)−0.0031 (8)
C70.0520 (9)0.0439 (9)0.0267 (7)−0.0031 (7)−0.0143 (6)−0.0043 (6)
C80.0549 (10)0.0503 (10)0.0432 (10)0.0020 (8)−0.0084 (8)−0.0048 (8)
C110.0412 (7)0.0365 (8)0.0304 (7)−0.0113 (6)−0.0098 (6)0.0025 (6)
C120.0391 (7)0.0359 (8)0.0267 (7)−0.0101 (6)−0.0066 (6)−0.0015 (6)
C130.0419 (8)0.0390 (8)0.0286 (7)−0.0097 (6)−0.0106 (6)0.0014 (6)
C140.0420 (8)0.0380 (8)0.0359 (8)−0.0077 (6)−0.0059 (6)−0.0017 (6)
C150.0510 (9)0.0437 (9)0.0324 (8)−0.0092 (7)−0.0039 (7)−0.0066 (6)
C160.0505 (8)0.0446 (9)0.0269 (7)−0.0106 (7)−0.0098 (6)−0.0014 (6)
O1A0.0377 (5)0.0495 (6)0.0293 (5)0.0023 (4)−0.0124 (4)0.0026 (4)
O2A0.0441 (6)0.0423 (6)0.0325 (6)0.0022 (4)−0.0157 (4)−0.0003 (4)
O3A0.0581 (8)0.0668 (9)0.0841 (10)0.0078 (7)−0.0173 (7)−0.0103 (8)
C1A0.0412 (8)0.0509 (9)0.0262 (7)−0.0060 (7)−0.0122 (6)0.0022 (6)
C2A0.0375 (7)0.0477 (9)0.0302 (8)−0.0037 (6)−0.0116 (6)0.0028 (6)
C3A0.0359 (7)0.0501 (9)0.0287 (7)−0.0047 (6)−0.0098 (6)0.0024 (6)
C4A0.0412 (8)0.0467 (9)0.0291 (7)−0.0010 (6)−0.0102 (6)0.0003 (6)
C5A0.0403 (8)0.0504 (9)0.0325 (8)−0.0037 (7)−0.0100 (6)0.0048 (6)
C6A0.0484 (9)0.0589 (11)0.0367 (8)0.0034 (8)−0.0142 (7)0.0039 (7)
C7A0.0551 (9)0.0480 (9)0.0362 (8)−0.0050 (7)−0.0220 (7)0.0008 (7)
C8A0.0390 (8)0.0485 (10)0.0733 (12)−0.0050 (7)−0.0055 (8)−0.0072 (9)
C11A0.0311 (7)0.0372 (8)0.0374 (8)−0.0056 (6)−0.0112 (6)0.0030 (6)
C12A0.0317 (7)0.0350 (8)0.0367 (8)−0.0081 (6)−0.0113 (6)0.0025 (6)
C13A0.0347 (7)0.0387 (8)0.0450 (8)−0.0091 (6)−0.0167 (6)0.0069 (6)
C14A0.0330 (7)0.0382 (8)0.0558 (10)−0.0081 (6)−0.0135 (7)0.0032 (7)
C15A0.0355 (8)0.0445 (9)0.0542 (10)−0.0032 (7)−0.0038 (7)−0.0076 (7)
C16A0.0385 (8)0.0496 (9)0.0386 (8)−0.0042 (7)−0.0089 (6)−0.0030 (7)
Geometric parameters (Å, °) top
O1—C111.3502 (18)O1A—C11A1.3548 (17)
O1—C11.4447 (17)O1A—C1A1.4395 (16)
O2—C121.3636 (17)O2A—C12A1.3622 (17)
O2—C71.4298 (16)O2A—C7A1.4358 (17)
O3—C81.209 (2)O3A—C8A1.178 (2)
C1—C21.506 (2)C1A—C2A1.508 (2)
C1—H1A0.9900C1A—H1A10.9900
C1—H1B0.9900C1A—H1A20.9900
C2—C31.5266 (19)C2A—C3A1.5249 (19)
C2—H2A0.9900C2A—H2A10.9900
C2—H2B0.9900C2A—H2A20.9900
C3—C41.522 (2)C3A—C4A1.519 (2)
C3—H3A0.9900C3A—H3A10.9900
C3—H3B0.9900C3A—H3A20.9900
C4—C51.519 (2)C4A—C5A1.520 (2)
C4—H4A0.9900C4A—H4A10.9900
C4—H4B0.9900C4A—H4A20.9900
C5—C61.519 (2)C5A—C6A1.519 (2)
C5—H5A0.9900C5A—H5A10.9900
C5—H5B0.9900C5A—H5A20.9900
C6—H6A0.9800C6A—H6A10.9800
C6—H6B0.9800C6A—H6A20.9800
C6—H6C0.9800C6A—H6A30.9800
C7—H7A0.9800C7A—H7A10.9800
C7—H7B0.9800C7A—H7A20.9800
C7—H7C0.9800C7A—H7A30.9800
C8—C141.456 (2)C8A—C14A1.490 (2)
C8—H80.9500C8A—H8A0.9500
C11—C161.392 (2)C11A—C16A1.393 (2)
C11—C121.4196 (19)C11A—C12A1.412 (2)
C12—C131.371 (2)C12A—C13A1.376 (2)
C13—C141.407 (2)C13A—C14A1.400 (2)
C13—H130.9500C13A—H13A0.9500
C14—C151.386 (2)C14A—C15A1.383 (2)
C15—C161.380 (2)C15A—C16A1.389 (2)
C15—H150.9500C15A—H15A0.9500
C16—H160.9500C16A—H16A0.9500
C11—O1—C1116.64 (11)C11A—O1A—C1A117.43 (11)
C12—O2—C7117.29 (11)C12A—O2A—C7A116.70 (11)
O1—C1—C2109.40 (12)O1A—C1A—C2A108.22 (11)
O1—C1—H1A109.8O1A—C1A—H1A1110.1
C2—C1—H1A109.8C2A—C1A—H1A1110.1
O1—C1—H1B109.8O1A—C1A—H1A2110.1
C2—C1—H1B109.8C2A—C1A—H1A2110.1
H1A—C1—H1B108.2H1A1—C1A—H1A2108.4
C1—C2—C3109.01 (12)C1A—C2A—C3A110.77 (12)
C1—C2—H2A109.9C1A—C2A—H2A1109.5
C3—C2—H2A109.9C3A—C2A—H2A1109.5
C1—C2—H2B109.9C1A—C2A—H2A2109.5
C3—C2—H2B109.9C3A—C2A—H2A2109.5
H2A—C2—H2B108.3H2A1—C2A—H2A2108.1
C4—C3—C2114.72 (12)C4A—C3A—C2A113.41 (12)
C4—C3—H3A108.6C4A—C3A—H3A1108.9
C2—C3—H3A108.6C2A—C3A—H3A1108.9
C4—C3—H3B108.6C4A—C3A—H3A2108.9
C2—C3—H3B108.6C2A—C3A—H3A2108.9
H3A—C3—H3B107.6H3A1—C3A—H3A2107.7
C5—C4—C3112.93 (12)C3A—C4A—C5A113.56 (12)
C5—C4—H4A109.0C3A—C4A—H4A1108.9
C3—C4—H4A109.0C5A—C4A—H4A1108.9
C5—C4—H4B109.0C3A—C4A—H4A2108.9
C3—C4—H4B109.0C5A—C4A—H4A2108.9
H4A—C4—H4B107.8H4A1—C4A—H4A2107.7
C4—C5—C6112.80 (13)C6A—C5A—C4A112.45 (12)
C4—C5—H5A109.0C6A—C5A—H5A1109.1
C6—C5—H5A109.0C4A—C5A—H5A1109.1
C4—C5—H5B109.0C6A—C5A—H5A2109.1
C6—C5—H5B109.0C4A—C5A—H5A2109.1
H5A—C5—H5B107.8H5A1—C5A—H5A2107.8
C5—C6—H6A109.5C5A—C6A—H6A1109.5
C5—C6—H6B109.5C5A—C6A—H6A2109.5
H6A—C6—H6B109.5H6A1—C6A—H6A2109.5
C5—C6—H6C109.5C5A—C6A—H6A3109.5
H6A—C6—H6C109.5H6A1—C6A—H6A3109.5
H6B—C6—H6C109.5H6A2—C6A—H6A3109.5
O2—C7—H7A109.5O2A—C7A—H7A1109.5
O2—C7—H7B109.5O2A—C7A—H7A2109.5
H7A—C7—H7B109.5H7A1—C7A—H7A2109.5
O2—C7—H7C109.5O2A—C7A—H7A3109.5
H7A—C7—H7C109.5H7A1—C7A—H7A3109.5
H7B—C7—H7C109.5H7A2—C7A—H7A3109.5
O3—C8—C14125.69 (16)O3A—C8A—C14A125.5 (2)
O3—C8—H8117.2O3A—C8A—H8A117.3
C14—C8—H8117.2C14A—C8A—H8A117.3
O1—C11—C16125.13 (13)O1A—C11A—C16A125.09 (13)
O1—C11—C12115.47 (12)O1A—C11A—C12A115.56 (12)
C16—C11—C12119.41 (14)C16A—C11A—C12A119.35 (13)
O2—C12—C13125.44 (13)O2A—C12A—C13A124.85 (13)
O2—C12—C11114.72 (12)O2A—C12A—C11A115.33 (12)
C13—C12—C11119.84 (13)C13A—C12A—C11A119.82 (14)
C12—C13—C14120.33 (13)C12A—C13A—C14A120.62 (14)
C12—C13—H13119.8C12A—C13A—H13A119.7
C14—C13—H13119.8C14A—C13A—H13A119.7
C15—C14—C13119.53 (14)C15A—C14A—C13A119.56 (14)
C15—C14—C8119.63 (14)C15A—C14A—C8A122.97 (15)
C13—C14—C8120.84 (14)C13A—C14A—C8A117.47 (15)
C16—C15—C14120.74 (14)C14A—C15A—C16A120.51 (15)
C16—C15—H15119.6C14A—C15A—H15A119.7
C14—C15—H15119.6C16A—C15A—H15A119.7
C15—C16—C11120.14 (14)C15A—C16A—C11A120.14 (15)
C15—C16—H16119.9C15A—C16A—H16A119.9
C11—C16—H16119.9C11A—C16A—H16A119.9
C11—O1—C1—C2−178.51 (12)C11A—O1A—C1A—C2A176.72 (12)
O1—C1—C2—C3−179.57 (12)O1A—C1A—C2A—C3A176.23 (12)
C1—C2—C3—C4176.08 (12)C1A—C2A—C3A—C4A177.66 (13)
C2—C3—C4—C5−179.02 (12)C2A—C3A—C4A—C5A178.51 (13)
C3—C4—C5—C6179.82 (13)C3A—C4A—C5A—C6A−179.53 (14)
C1—O1—C11—C16−1.5 (2)C1A—O1A—C11A—C16A−3.7 (2)
C1—O1—C11—C12178.79 (12)C1A—O1A—C11A—C12A176.50 (12)
C7—O2—C12—C13−0.3 (2)C7A—O2A—C12A—C13A7.2 (2)
C7—O2—C12—C11179.93 (12)C7A—O2A—C12A—C11A−173.04 (12)
O1—C11—C12—O20.82 (18)O1A—C11A—C12A—O2A−0.93 (18)
C16—C11—C12—O2−178.89 (13)C16A—C11A—C12A—O2A179.30 (13)
O1—C11—C12—C13−179.01 (12)O1A—C11A—C12A—C13A178.89 (12)
C16—C11—C12—C131.3 (2)C16A—C11A—C12A—C13A−0.9 (2)
O2—C12—C13—C14179.44 (14)O2A—C12A—C13A—C14A−179.87 (13)
C11—C12—C13—C14−0.8 (2)C11A—C12A—C13A—C14A0.3 (2)
C12—C13—C14—C15−0.2 (2)C12A—C13A—C14A—C15A0.4 (2)
C12—C13—C14—C8179.23 (14)C12A—C13A—C14A—C8A179.73 (13)
O3—C8—C14—C15−179.18 (18)O3A—C8A—C14A—C15A4.4 (3)
O3—C8—C14—C131.4 (3)O3A—C8A—C14A—C13A−174.92 (18)
C13—C14—C15—C160.6 (2)C13A—C14A—C15A—C16A−0.6 (2)
C8—C14—C15—C16−178.82 (15)C8A—C14A—C15A—C16A−179.89 (15)
C14—C15—C16—C11−0.1 (2)C14A—C15A—C16A—C11A0.1 (2)
O1—C11—C16—C15179.45 (14)O1A—C11A—C16A—C15A−179.05 (14)
C12—C11—C16—C15−0.9 (2)C12A—C11A—C16A—C15A0.7 (2)
Acknowledgements top

AA is grateful to the Higher Education Commission of Pakistan for financial support for the PhD program under scholarship No.[II-0317109].

references
References top

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.

Ashalekshmi, V. S. & Mohanan, K. (2008). Asian J. Chem. 20, 623–628.

Charles, R. E., Ponrasu, T., Sivakumar, R. & Divakar, S. (2009). Biotechnol. Appl.Biochem. pp. 177–184.

Guo, H. M., Zhao, G. L. & Yu, Y. Y. (2008). Chin. J. Inorg. Chem. 24, 1393–1399.

Li, Y. (2008). Chin. J. Struct. Chem. 27, 1089–1092.

Liang, J. A., Wu, S. L., Lo, H. Y., Hsiang, C. Y. & Ho, T. Y. (2009). Mol. Pharmacol. 75, 151–157.

Lim, E. J., Kang, H. J., Jung, H. J., Song, S., Lim, C. J. & Park, E. H. (2008). Biomol. Ther. 16, 132–136.

Neelakantan, M. A., Marriappan, S. S., Dharmaraja, J., Jeyakumar, T. & Muthukumaran, K. (2008). Spectrochim Acta A Mol. Biomol. Spectrosc. 71, 628–635.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.

Williamson, A. W. (1852). Q. Rev. Chem. Soc. 4, 229–239.

Xia, C. N., Li, H. B., Liu, F. & Hu, W. X. (2008). Bioorg. Med. Chem. Lett. 18, 6553–6557.

Yan, Y. Q., Zhang, B., Wang, L., Xie, Y. H., Peng, T., Bai, B. & Zhou, P. K. (2007). Cancer Lett. 252, 280–289.