Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 May 14;65(Pt 6):o1281. doi: 10.1107/S1600536809017358

4-Hex­yloxy-3-methoxy­benzaldehyde

Asghar Abbas a, M Khawar Rauf a, Michael Bolte b, Aurangzeb Hasan a,*
PMCID: PMC2969539  PMID: 21583143

Abstract

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).

Related literature

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 activity. Bromovanin (6-bromine-5-hydroxy-4-methoxybenzaldehyde) (Yan et al., 2007 ▶) and caffeate analogues (Xia et al., 2008 ▶) derived from vanillin exhibit a potent anti-proliferative effect on a broad spectrum of cancer cell lines. For the biological activity of vanillin, see: Liang et al. (2009 ▶), and for glycosides of vanillin, see: Charles et al. (2009 ▶); Lim et al. (2008 ▶). For details of the synthesis, see: Williamson (1852 ▶). For related structures, see: Li (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).graphic file with name e-65-o1281-scheme1.jpg

Experimental

Crystal data

  • C14H20O3

  • M r = 236.30

  • Triclinic, Inline graphic

  • a = 9.2788 (5) Å

  • b = 9.3894 (6) Å

  • c = 15.8501 (9) Å

  • α = 88.099 (5)°

  • β = 75.065 (5)°

  • γ = 80.262 (5)°

  • V = 1314.95 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.42 × 0.37 × 0.36 mm

Data collection

  • STOE IPDS II two-circle diffractometer

  • Absorption correction: none

  • 17943 measured reflections

  • 4919 independent reflections

  • 3862 reflections with I > 2σ(I)

  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049

  • wR(F 2) = 0.144

  • S = 1.06

  • 4919 reflections

  • 309 parameters

  • H-atom parameters constrained

  • Δρmax = 0.69 e Å−3

  • Δρmin = −0.28 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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.

Supplementary Material

Crystal structure: contains datablocks I, global_rauf53. DOI: 10.1107/S1600536809017358/hg2506sup1.cif

e-65-o1281-sup1.cif (24.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017358/hg2506Isup2.hkl

e-65-o1281-Isup2.hkl (240.9KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

Molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C14H20O3 Z = 4
Mr = 236.30 F(000) = 512
Triclinic, P1 Dx = 1.194 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 9.2788 (5) Å Cell parameters from 16295 reflections
b = 9.3894 (6) Å θ = 3.5–25.9°
c = 15.8501 (9) Å µ = 0.08 mm−1
α = 88.099 (5)° T = 173 K
β = 75.065 (5)° Block, colourless
γ = 80.262 (5)° 0.42 × 0.37 × 0.36 mm
V = 1314.95 (13) Å3
Open in a new tab

Data collection

STOE IPDS II two-circle-diffractometer 3862 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.046
graphite θmax = 25.6°, θmin = 3.4°
ω scans h = −11→11
17943 measured reflections k = −11→11
4919 independent reflections l = −19→19
Open in a new tab

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144 H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0794P)2 + 0.213P] where P = (Fo2 + 2Fc2)/3
4919 reflections (Δ/σ)max = 0.001
309 parameters Δρmax = 0.69 e Å−3
0 restraints Δρmin = −0.28 e Å−3
Open in a new tab

Special details

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.
Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.65027 (12) 0.60519 (12) 0.99368 (6) 0.0403 (3)
O2 0.69937 (12) 0.56660 (11) 1.14584 (6) 0.0397 (3)
O3 1.13475 (16) 0.12211 (15) 1.10444 (9) 0.0648 (4)
C1 0.62080 (18) 0.63144 (18) 0.90887 (9) 0.0412 (4)
H1A 0.5870 0.5463 0.8897 0.049*
H1B 0.7146 0.6475 0.8656 0.049*
C2 0.50012 (17) 0.76247 (17) 0.91409 (9) 0.0395 (4)
H2A 0.5342 0.8479 0.9327 0.047*
H2B 0.4064 0.7468 0.9576 0.047*
C3 0.46892 (16) 0.78865 (17) 0.82439 (9) 0.0376 (3)
H3A 0.5625 0.8087 0.7825 0.045*
H3B 0.4442 0.6990 0.8046 0.045*
C4 0.34118 (16) 0.91241 (17) 0.82143 (9) 0.0372 (3)
H4A 0.2474 0.8935 0.8636 0.045*
H4B 0.3664 1.0029 0.8398 0.045*
C5 0.31230 (17) 0.93292 (17) 0.73137 (10) 0.0399 (4)
H5A 0.2874 0.8423 0.7129 0.048*
H5B 0.4059 0.9522 0.6892 0.048*
C6 0.1844 (2) 1.05620 (19) 0.72871 (12) 0.0510 (4)
H6A 0.1701 1.0643 0.6695 0.076*
H6B 0.2097 1.1468 0.7452 0.076*
H6C 0.0910 1.0371 0.7697 0.076*
C7 0.72298 (18) 0.55017 (17) 1.23152 (9) 0.0405 (4)
H7A 0.7067 0.4537 1.2532 0.061*
H7B 0.6517 0.6235 1.2707 0.061*
H7C 0.8268 0.5621 1.2294 0.061*
C8 1.0993 (2) 0.1514 (2) 1.03692 (11) 0.0514 (4)
H8 1.1534 0.0935 0.9871 0.062*
C11 0.75896 (17) 0.49258 (16) 0.99937 (9) 0.0354 (3)
C12 0.78770 (16) 0.47099 (16) 1.08300 (9) 0.0338 (3)
C13 0.89766 (16) 0.36073 (16) 1.09506 (9) 0.0359 (3)
H13 0.9177 0.3470 1.1509 0.043*
C14 0.98097 (17) 0.26779 (17) 1.02520 (10) 0.0393 (3)
C15 0.95082 (18) 0.28820 (18) 0.94401 (10) 0.0433 (4)
H15 1.0063 0.2250 0.8969 0.052*
C16 0.84110 (18) 0.39934 (17) 0.93083 (9) 0.0403 (4)
H16 0.8216 0.4122 0.8749 0.048*
O1A 0.54463 (11) 0.20255 (12) 0.59371 (6) 0.0393 (3)
O2A 0.57832 (11) 0.17700 (11) 0.75033 (6) 0.0396 (3)
O3A 1.10136 (16) −0.29636 (16) 0.61496 (10) 0.0718 (4)
C1A 0.52746 (17) 0.22746 (18) 0.50646 (9) 0.0390 (3)
H1A1 0.5165 0.1365 0.4807 0.047*
H1A2 0.6177 0.2621 0.4693 0.047*
C2A 0.38839 (16) 0.33951 (18) 0.51114 (9) 0.0384 (3)
H2A1 0.3969 0.4274 0.5411 0.046*
H2A2 0.2980 0.3017 0.5456 0.046*
C3A 0.36975 (16) 0.37813 (18) 0.41991 (9) 0.0382 (3)
H3A1 0.4591 0.4187 0.3866 0.046*
H3A2 0.3666 0.2888 0.3894 0.046*
C4A 0.22797 (17) 0.48624 (18) 0.42019 (9) 0.0395 (3)
H4A1 0.2298 0.5745 0.4521 0.047*
H4A2 0.1385 0.4446 0.4522 0.047*
C5A 0.21109 (17) 0.52794 (18) 0.32935 (10) 0.0415 (4)
H5A1 0.3006 0.5693 0.2970 0.050*
H5A2 0.2079 0.4401 0.2975 0.050*
C6A 0.06916 (19) 0.6370 (2) 0.33156 (11) 0.0489 (4)
H6A1 0.0631 0.6603 0.2717 0.073*
H6A2 0.0728 0.7251 0.3618 0.073*
H6A3 −0.0200 0.5959 0.3626 0.073*
C7A 0.60438 (19) 0.17584 (18) 0.83582 (10) 0.0449 (4)
H7A1 0.5974 0.0800 0.8614 0.067*
H7A2 0.5281 0.2484 0.8730 0.067*
H7A3 0.7054 0.1984 0.8314 0.067*
C8A 1.00578 (19) −0.2192 (2) 0.66439 (14) 0.0553 (5)
H8A 1.0044 −0.2273 0.7245 0.066*
C11A 0.65958 (15) 0.09930 (16) 0.60415 (10) 0.0349 (3)
C12A 0.67768 (15) 0.08413 (16) 0.68992 (9) 0.0337 (3)
C13A 0.78979 (16) −0.01963 (16) 0.70729 (10) 0.0380 (3)
H13A 0.8014 −0.0300 0.7651 0.046*
C14A 0.88682 (16) −0.11002 (17) 0.64056 (11) 0.0417 (4)
C15A 0.87018 (17) −0.09402 (18) 0.55633 (11) 0.0464 (4)
H15A 0.9365 −0.1546 0.5108 0.056*
C16A 0.75726 (17) 0.00993 (18) 0.53781 (10) 0.0427 (4)
H16A 0.7466 0.0201 0.4798 0.051*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0492 (6) 0.0449 (6) 0.0270 (5) −0.0025 (5) −0.0137 (4) 0.0013 (4)
O2 0.0483 (6) 0.0419 (6) 0.0271 (5) 0.0031 (4) −0.0126 (4) −0.0041 (4)
O3 0.0685 (8) 0.0662 (9) 0.0524 (8) 0.0149 (7) −0.0189 (6) 0.0002 (6)
C1 0.0522 (9) 0.0488 (9) 0.0261 (7) −0.0103 (7) −0.0153 (6) 0.0041 (6)
C2 0.0456 (8) 0.0448 (9) 0.0309 (8) −0.0121 (7) −0.0124 (6) 0.0037 (6)
C3 0.0382 (7) 0.0468 (9) 0.0300 (7) −0.0104 (6) −0.0105 (6) 0.0027 (6)
C4 0.0374 (7) 0.0426 (9) 0.0329 (8) −0.0102 (6) −0.0090 (6) −0.0014 (6)
C5 0.0394 (7) 0.0451 (9) 0.0368 (8) −0.0049 (6) −0.0136 (6) −0.0009 (6)
C6 0.0560 (10) 0.0499 (10) 0.0481 (10) 0.0034 (8) −0.0225 (8) −0.0031 (8)
C7 0.0520 (9) 0.0439 (9) 0.0267 (7) −0.0031 (7) −0.0143 (6) −0.0043 (6)
C8 0.0549 (10) 0.0503 (10) 0.0432 (10) 0.0020 (8) −0.0084 (8) −0.0048 (8)
C11 0.0412 (7) 0.0365 (8) 0.0304 (7) −0.0113 (6) −0.0098 (6) 0.0025 (6)
C12 0.0391 (7) 0.0359 (8) 0.0267 (7) −0.0101 (6) −0.0066 (6) −0.0015 (6)
C13 0.0419 (8) 0.0390 (8) 0.0286 (7) −0.0097 (6) −0.0106 (6) 0.0014 (6)
C14 0.0420 (8) 0.0380 (8) 0.0359 (8) −0.0077 (6) −0.0059 (6) −0.0017 (6)
C15 0.0510 (9) 0.0437 (9) 0.0324 (8) −0.0092 (7) −0.0039 (7) −0.0066 (6)
C16 0.0505 (8) 0.0446 (9) 0.0269 (7) −0.0106 (7) −0.0098 (6) −0.0014 (6)
O1A 0.0377 (5) 0.0495 (6) 0.0293 (5) 0.0023 (4) −0.0124 (4) 0.0026 (4)
O2A 0.0441 (6) 0.0423 (6) 0.0325 (6) 0.0022 (4) −0.0157 (4) −0.0003 (4)
O3A 0.0581 (8) 0.0668 (9) 0.0841 (10) 0.0078 (7) −0.0173 (7) −0.0103 (8)
C1A 0.0412 (8) 0.0509 (9) 0.0262 (7) −0.0060 (7) −0.0122 (6) 0.0022 (6)
C2A 0.0375 (7) 0.0477 (9) 0.0302 (8) −0.0037 (6) −0.0116 (6) 0.0028 (6)
C3A 0.0359 (7) 0.0501 (9) 0.0287 (7) −0.0047 (6) −0.0098 (6) 0.0024 (6)
C4A 0.0412 (8) 0.0467 (9) 0.0291 (7) −0.0010 (6) −0.0102 (6) 0.0003 (6)
C5A 0.0403 (8) 0.0504 (9) 0.0325 (8) −0.0037 (7) −0.0100 (6) 0.0048 (6)
C6A 0.0484 (9) 0.0589 (11) 0.0367 (8) 0.0034 (8) −0.0142 (7) 0.0039 (7)
C7A 0.0551 (9) 0.0480 (9) 0.0362 (8) −0.0050 (7) −0.0220 (7) 0.0008 (7)
C8A 0.0390 (8) 0.0485 (10) 0.0733 (12) −0.0050 (7) −0.0055 (8) −0.0072 (9)
C11A 0.0311 (7) 0.0372 (8) 0.0374 (8) −0.0056 (6) −0.0112 (6) 0.0030 (6)
C12A 0.0317 (7) 0.0350 (8) 0.0367 (8) −0.0081 (6) −0.0113 (6) 0.0025 (6)
C13A 0.0347 (7) 0.0387 (8) 0.0450 (8) −0.0091 (6) −0.0167 (6) 0.0069 (6)
C14A 0.0330 (7) 0.0382 (8) 0.0558 (10) −0.0081 (6) −0.0135 (7) 0.0032 (7)
C15A 0.0355 (8) 0.0445 (9) 0.0542 (10) −0.0032 (7) −0.0038 (7) −0.0076 (7)
C16A 0.0385 (8) 0.0496 (9) 0.0386 (8) −0.0042 (7) −0.0089 (6) −0.0030 (7)
Open in a new tab

Geometric parameters (Å, °)

O1—C11 1.3502 (18) O1A—C11A 1.3548 (17)
O1—C1 1.4447 (17) O1A—C1A 1.4395 (16)
O2—C12 1.3636 (17) O2A—C12A 1.3622 (17)
O2—C7 1.4298 (16) O2A—C7A 1.4358 (17)
O3—C8 1.209 (2) O3A—C8A 1.178 (2)
C1—C2 1.506 (2) C1A—C2A 1.508 (2)
C1—H1A 0.9900 C1A—H1A1 0.9900
C1—H1B 0.9900 C1A—H1A2 0.9900
C2—C3 1.5266 (19) C2A—C3A 1.5249 (19)
C2—H2A 0.9900 C2A—H2A1 0.9900
C2—H2B 0.9900 C2A—H2A2 0.9900
C3—C4 1.522 (2) C3A—C4A 1.519 (2)
C3—H3A 0.9900 C3A—H3A1 0.9900
C3—H3B 0.9900 C3A—H3A2 0.9900
C4—C5 1.519 (2) C4A—C5A 1.520 (2)
C4—H4A 0.9900 C4A—H4A1 0.9900
C4—H4B 0.9900 C4A—H4A2 0.9900
C5—C6 1.519 (2) C5A—C6A 1.519 (2)
C5—H5A 0.9900 C5A—H5A1 0.9900
C5—H5B 0.9900 C5A—H5A2 0.9900
C6—H6A 0.9800 C6A—H6A1 0.9800
C6—H6B 0.9800 C6A—H6A2 0.9800
C6—H6C 0.9800 C6A—H6A3 0.9800
C7—H7A 0.9800 C7A—H7A1 0.9800
C7—H7B 0.9800 C7A—H7A2 0.9800
C7—H7C 0.9800 C7A—H7A3 0.9800
C8—C14 1.456 (2) C8A—C14A 1.490 (2)
C8—H8 0.9500 C8A—H8A 0.9500
C11—C16 1.392 (2) C11A—C16A 1.393 (2)
C11—C12 1.4196 (19) C11A—C12A 1.412 (2)
C12—C13 1.371 (2) C12A—C13A 1.376 (2)
C13—C14 1.407 (2) C13A—C14A 1.400 (2)
C13—H13 0.9500 C13A—H13A 0.9500
C14—C15 1.386 (2) C14A—C15A 1.383 (2)
C15—C16 1.380 (2) C15A—C16A 1.389 (2)
C15—H15 0.9500 C15A—H15A 0.9500
C16—H16 0.9500 C16A—H16A 0.9500
C11—O1—C1 116.64 (11) C11A—O1A—C1A 117.43 (11)
C12—O2—C7 117.29 (11) C12A—O2A—C7A 116.70 (11)
O1—C1—C2 109.40 (12) O1A—C1A—C2A 108.22 (11)
O1—C1—H1A 109.8 O1A—C1A—H1A1 110.1
C2—C1—H1A 109.8 C2A—C1A—H1A1 110.1
O1—C1—H1B 109.8 O1A—C1A—H1A2 110.1
C2—C1—H1B 109.8 C2A—C1A—H1A2 110.1
H1A—C1—H1B 108.2 H1A1—C1A—H1A2 108.4
C1—C2—C3 109.01 (12) C1A—C2A—C3A 110.77 (12)
C1—C2—H2A 109.9 C1A—C2A—H2A1 109.5
C3—C2—H2A 109.9 C3A—C2A—H2A1 109.5
C1—C2—H2B 109.9 C1A—C2A—H2A2 109.5
C3—C2—H2B 109.9 C3A—C2A—H2A2 109.5
H2A—C2—H2B 108.3 H2A1—C2A—H2A2 108.1
C4—C3—C2 114.72 (12) C4A—C3A—C2A 113.41 (12)
C4—C3—H3A 108.6 C4A—C3A—H3A1 108.9
C2—C3—H3A 108.6 C2A—C3A—H3A1 108.9
C4—C3—H3B 108.6 C4A—C3A—H3A2 108.9
C2—C3—H3B 108.6 C2A—C3A—H3A2 108.9
H3A—C3—H3B 107.6 H3A1—C3A—H3A2 107.7
C5—C4—C3 112.93 (12) C3A—C4A—C5A 113.56 (12)
C5—C4—H4A 109.0 C3A—C4A—H4A1 108.9
C3—C4—H4A 109.0 C5A—C4A—H4A1 108.9
C5—C4—H4B 109.0 C3A—C4A—H4A2 108.9
C3—C4—H4B 109.0 C5A—C4A—H4A2 108.9
H4A—C4—H4B 107.8 H4A1—C4A—H4A2 107.7
C4—C5—C6 112.80 (13) C6A—C5A—C4A 112.45 (12)
C4—C5—H5A 109.0 C6A—C5A—H5A1 109.1
C6—C5—H5A 109.0 C4A—C5A—H5A1 109.1
C4—C5—H5B 109.0 C6A—C5A—H5A2 109.1
C6—C5—H5B 109.0 C4A—C5A—H5A2 109.1
H5A—C5—H5B 107.8 H5A1—C5A—H5A2 107.8
C5—C6—H6A 109.5 C5A—C6A—H6A1 109.5
C5—C6—H6B 109.5 C5A—C6A—H6A2 109.5
H6A—C6—H6B 109.5 H6A1—C6A—H6A2 109.5
C5—C6—H6C 109.5 C5A—C6A—H6A3 109.5
H6A—C6—H6C 109.5 H6A1—C6A—H6A3 109.5
H6B—C6—H6C 109.5 H6A2—C6A—H6A3 109.5
O2—C7—H7A 109.5 O2A—C7A—H7A1 109.5
O2—C7—H7B 109.5 O2A—C7A—H7A2 109.5
H7A—C7—H7B 109.5 H7A1—C7A—H7A2 109.5
O2—C7—H7C 109.5 O2A—C7A—H7A3 109.5
H7A—C7—H7C 109.5 H7A1—C7A—H7A3 109.5
H7B—C7—H7C 109.5 H7A2—C7A—H7A3 109.5
O3—C8—C14 125.69 (16) O3A—C8A—C14A 125.5 (2)
O3—C8—H8 117.2 O3A—C8A—H8A 117.3
C14—C8—H8 117.2 C14A—C8A—H8A 117.3
O1—C11—C16 125.13 (13) O1A—C11A—C16A 125.09 (13)
O1—C11—C12 115.47 (12) O1A—C11A—C12A 115.56 (12)
C16—C11—C12 119.41 (14) C16A—C11A—C12A 119.35 (13)
O2—C12—C13 125.44 (13) O2A—C12A—C13A 124.85 (13)
O2—C12—C11 114.72 (12) O2A—C12A—C11A 115.33 (12)
C13—C12—C11 119.84 (13) C13A—C12A—C11A 119.82 (14)
C12—C13—C14 120.33 (13) C12A—C13A—C14A 120.62 (14)
C12—C13—H13 119.8 C12A—C13A—H13A 119.7
C14—C13—H13 119.8 C14A—C13A—H13A 119.7
C15—C14—C13 119.53 (14) C15A—C14A—C13A 119.56 (14)
C15—C14—C8 119.63 (14) C15A—C14A—C8A 122.97 (15)
C13—C14—C8 120.84 (14) C13A—C14A—C8A 117.47 (15)
C16—C15—C14 120.74 (14) C14A—C15A—C16A 120.51 (15)
C16—C15—H15 119.6 C14A—C15A—H15A 119.7
C14—C15—H15 119.6 C16A—C15A—H15A 119.7
C15—C16—C11 120.14 (14) C15A—C16A—C11A 120.14 (15)
C15—C16—H16 119.9 C15A—C16A—H16A 119.9
C11—C16—H16 119.9 C11A—C16A—H16A 119.9
C11—O1—C1—C2 −178.51 (12) C11A—O1A—C1A—C2A 176.72 (12)
O1—C1—C2—C3 −179.57 (12) O1A—C1A—C2A—C3A 176.23 (12)
C1—C2—C3—C4 176.08 (12) C1A—C2A—C3A—C4A 177.66 (13)
C2—C3—C4—C5 −179.02 (12) C2A—C3A—C4A—C5A 178.51 (13)
C3—C4—C5—C6 179.82 (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—C12 178.79 (12) C1A—O1A—C11A—C12A 176.50 (12)
C7—O2—C12—C13 −0.3 (2) C7A—O2A—C12A—C13A 7.2 (2)
C7—O2—C12—C11 179.93 (12) C7A—O2A—C12A—C11A −173.04 (12)
O1—C11—C12—O2 0.82 (18) O1A—C11A—C12A—O2A −0.93 (18)
C16—C11—C12—O2 −178.89 (13) C16A—C11A—C12A—O2A 179.30 (13)
O1—C11—C12—C13 −179.01 (12) O1A—C11A—C12A—C13A 178.89 (12)
C16—C11—C12—C13 1.3 (2) C16A—C11A—C12A—C13A −0.9 (2)
O2—C12—C13—C14 179.44 (14) O2A—C12A—C13A—C14A −179.87 (13)
C11—C12—C13—C14 −0.8 (2) C11A—C12A—C13A—C14A 0.3 (2)
C12—C13—C14—C15 −0.2 (2) C12A—C13A—C14A—C15A 0.4 (2)
C12—C13—C14—C8 179.23 (14) C12A—C13A—C14A—C8A 179.73 (13)
O3—C8—C14—C15 −179.18 (18) O3A—C8A—C14A—C15A 4.4 (3)
O3—C8—C14—C13 1.4 (3) O3A—C8A—C14A—C13A −174.92 (18)
C13—C14—C15—C16 0.6 (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—C11A 0.1 (2)
O1—C11—C16—C15 179.45 (14) O1A—C11A—C16A—C15A −179.05 (14)
C12—C11—C16—C15 −0.9 (2) C12A—C11A—C16A—C15A 0.7 (2)
Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2506).

References

  1. 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.
  2. Ashalekshmi, V. S. & Mohanan, K. (2008). Asian J. Chem.20, 623–628.
  3. Charles, R. E., Ponrasu, T., Sivakumar, R. & Divakar, S. (2009). Biotechnol. Appl. Biochem. pp. 177–184. [DOI] [PubMed]
  4. Guo, H. M., Zhao, G. L. & Yu, Y. Y. (2008). Chin. J. Inorg. Chem.24, 1393–1399.
  5. Li, Y. (2008). Chin. J. Struct. Chem.27, 1089–1092.
  6. Liang, J. A., Wu, S. L., Lo, H. Y., Hsiang, C. Y. & Ho, T. Y. (2009). Mol. Pharmacol.75, 151–157. [DOI] [PubMed]
  7. Lim, E. J., Kang, H. J., Jung, H. J., Song, S., Lim, C. J. & Park, E. H. (2008). Biomol. Ther.16, 132–136.
  8. Neelakantan, M. A., Marriappan, S. S., Dharmaraja, J., Jeyakumar, T. & Muthukumaran, K. (2008). Spectrochim Acta Part A, 71, 628–635. [DOI] [PubMed]
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  10. Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.
  11. Williamson, A. W. (1852). Q. Rev. Chem. Soc.4, 229–239.
  12. Xia, C. N., Li, H. B., Liu, F. & Hu, W. X. (2008). Bioorg. Med. Chem. Lett.18, 6553–6557. [DOI] [PubMed]
  13. Yan, Y. Q., Zhang, B., Wang, L., Xie, Y. H., Peng, T., Bai, B. & Zhou, P. K. (2007). Cancer Lett.252, 280–289. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global_rauf53. DOI: 10.1107/S1600536809017358/hg2506sup1.cif

e-65-o1281-sup1.cif (24.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017358/hg2506Isup2.hkl

e-65-o1281-Isup2.hkl (240.9KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES