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(E)-1-(4-Decyloxyphenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
aDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, bDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my
In the title compound, C25H32O3, the enone group adopts an s-cis conformation. The alkoxy chain is in an all-trans conformation. The dihedral angle between the benzene rings is 7.86 (5)°. In the crystal, molecules are connected by pairs of O—H⋯O hydrogen bonds, forming inversion dimers and giving R22(10) rings. Within these dimers, weak C—H⋯O hydrogen bonds form two R22(7) rings. In the crystal, the approximately planar molecules [largest deviation for an atom being 0.4737 (12) Å for the terminal C atom of the alkoxy chain] are arranged in sheets parallel to (20-1). Weak C—H⋯π interactions are also observed.
Related literature
For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004
); Won et al. (2005
); Zhao et al. (2005
); Satyanarayana et al. (2004
). For related structures, see: Razak et al. (2009
); Ngaini et al. (2010
, 2011
). For graph-set theory, see: Bernstein et al. (1995
). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986)
. For standard bond-length data, see: Allen et al. (1987
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009
).
Supporting information
https://doi.org/10.1107/S160053681203872X/lh5525sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681203872X/lh5525Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681203872X/lh5525Isup3.cml
A mixture of 2-hydroxybenzaldehyde (2.44 ml, 20 mmol), 4-decyloxyacetophenone (6.65 g, 20 mmol) and KOH (4.04 g, 72 mmol) in methanol (60 ml) was heated at reflux for 12 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2N). After redissolving in hexane followed by few days of slow evaporation, crystals were collected.
The O-bound H atom was located in a difference Fourier map and refined freely with O–H = 0.943 (17) Å. The remaining H atoms were placed in calculated positions with C–H = 0.93–0.97 Å. The Uiso values were constrained to be 1.5Ueq (methyl-H atom) and 1.2Ueq (other H atoms). The rotating model group was applied for the methyl group.
Chalcones have displayed an impressive array of biological activities and are extensively reported (Xue et al., 2004; Bhat et al., 2005; Won et al., 2005; Zhao et al., 2005 and Satyanarayana et al., 2004). Here in, we report the
of the title compound (I).In (I), Fig. 1, the bond lengths observed are comparable with standard reported values (Allen et al., 1987). The enone (O2/C7–C9) moiety adopts a s-cis conformation with a torsion angle of -6.41 (15)°. The mean plane through the enone (O2/C7–C9) moiety form dihedral angles of 2.80 (6) and 7.26 (6)° respectively with the benzene (C1–C6 and C10–C15) rings. The dihedral angle between the two benzene rings is 7.86 (5)°.
An observed widening of the C1–C6–C7 and C6–C7–C8 angles of 122.85 (8) and 126.23 (8)° respectively, may be the consequence of the short contact between H1A and H8A (2.19 Å). Similarly, the slight distortion of the O3–C13–C14 angle to 125.18 (9)° may be the result of a close H14A and H16B (2.37 Å) contact. The geometric parameters are consistent to those observed in closely related structures (Razak et al., 2009; Ngaini et al., 2010; Ngaini et al., 2011).
The alkoxy chain adopts an all
conformation with the difference from the ideal values of the torsion angles ranging from 0.98 (7)° to 7.98 (9)°. The C16–O3–C13–C14 torsion angle of 4.73 (13)° indicate that atoms C16 and O3 and the attached benzene ring are approximately co-planar. The alkoxy chain appears to deviate from co-planarity with the ring for atoms further away i.e. C24 and C25. The dihedral angle between the least-square plane through atoms O3/C16–C25 [maximum deviation = 0.2507 (10)Å at C25] and the attached benzene ring is 15.20 (5)°.In the crystal (Fig. 2), molecules are connected by a pair of O1—H1O1···O2i and a pair of weak C7—H7A···O1i hydrogen bonds to form a R22(10) ring and two R22(7) rings within inversion dimers. These dimers are arranged into sheets parallel to (201). Weak C—H···π interactions (Table 1) are also observed.
For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Won et al. (2005); Zhao et al. (2005); Satyanarayana et al. (2004). For related structures, see: Razak et al. (2009); Ngaini et al. (2010, 2011). For graph-set theory, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C25H32O3 | Z = 2 |
Mr = 380.51 | F(000) = 412 |
Triclinic, P1 | Dx = 1.188 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6674 (13) Å | Cell parameters from 7111 reflections |
b = 10.9865 (17) Å | θ = 2.5–33.7° |
c = 12.1352 (19) Å | µ = 0.08 mm−1 |
α = 74.405 (3)° | T = 100 K |
β = 72.891 (3)° | Block, yellow |
γ = 85.981 (4)° | 0.62 × 0.15 × 0.14 mm |
V = 1063.7 (3) Å3 |
Bruker APEXII DUO CCD area-detector diffractometer | 8434 independent reflections |
Radiation source: fine-focus sealed tube | 6213 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 33.9°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.955, Tmax = 0.990 | k = −17→17 |
30192 measured reflections | l = −18→18 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0957P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3 |
8434 reflections | (Δ/σ)max < 0.001 |
258 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C25H32O3 | γ = 85.981 (4)° |
Mr = 380.51 | V = 1063.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6674 (13) Å | Mo Kα radiation |
b = 10.9865 (17) Å | µ = 0.08 mm−1 |
c = 12.1352 (19) Å | T = 100 K |
α = 74.405 (3)° | 0.62 × 0.15 × 0.14 mm |
β = 72.891 (3)° |
Bruker APEXII DUO CCD area-detector diffractometer | 8434 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 6213 reflections with I > 2σ(I) |
Tmin = 0.955, Tmax = 0.990 | Rint = 0.034 |
30192 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.63 e Å−3 |
8434 reflections | Δρmin = −0.20 e Å−3 |
258 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.97173 (10) | 0.64655 (7) | 0.51189 (7) | 0.03236 (17) | |
O2 | 0.94280 (8) | 0.34433 (6) | 0.29484 (6) | 0.02528 (14) | |
O3 | 0.72670 (9) | 0.27611 (6) | −0.13495 (6) | 0.02605 (15) | |
C1 | 0.83637 (12) | 0.82610 (8) | 0.26041 (8) | 0.02406 (17) | |
H1A | 0.8087 | 0.8127 | 0.1961 | 0.029* | |
C2 | 0.82611 (13) | 0.94641 (9) | 0.27668 (9) | 0.0290 (2) | |
H2A | 0.7910 | 1.0128 | 0.2241 | 0.035* | |
C3 | 0.86846 (12) | 0.96808 (9) | 0.37210 (9) | 0.02815 (19) | |
H3A | 0.8630 | 1.0493 | 0.3825 | 0.034* | |
C4 | 0.91859 (11) | 0.86906 (8) | 0.45150 (9) | 0.02482 (17) | |
H4A | 0.9466 | 0.8836 | 0.5152 | 0.030* | |
C5 | 0.92699 (11) | 0.74707 (8) | 0.43560 (8) | 0.02130 (16) | |
C6 | 0.88752 (10) | 0.72389 (8) | 0.33845 (7) | 0.01911 (15) | |
C7 | 0.89920 (10) | 0.59575 (8) | 0.32398 (8) | 0.02062 (16) | |
H7A | 0.9260 | 0.5326 | 0.3836 | 0.025* | |
C8 | 0.87499 (11) | 0.56017 (8) | 0.23288 (8) | 0.02137 (16) | |
H8A | 0.8464 | 0.6213 | 0.1727 | 0.026* | |
C9 | 0.89166 (10) | 0.42876 (8) | 0.22394 (7) | 0.01902 (15) | |
C10 | 0.84626 (10) | 0.39669 (8) | 0.12615 (7) | 0.01838 (15) | |
C11 | 0.87712 (10) | 0.27355 (8) | 0.11183 (8) | 0.02067 (16) | |
H11A | 0.9258 | 0.2158 | 0.1626 | 0.025* | |
C12 | 0.83636 (11) | 0.23708 (8) | 0.02362 (8) | 0.02239 (16) | |
H12A | 0.8581 | 0.1555 | 0.0151 | 0.027* | |
C13 | 0.76235 (10) | 0.32268 (8) | −0.05314 (7) | 0.02090 (16) | |
C14 | 0.73151 (11) | 0.44598 (8) | −0.04146 (8) | 0.02183 (16) | |
H14A | 0.6834 | 0.5036 | −0.0927 | 0.026* | |
C15 | 0.77373 (10) | 0.48127 (8) | 0.04772 (7) | 0.02078 (16) | |
H15A | 0.7532 | 0.5633 | 0.0554 | 0.025* | |
C16 | 0.66227 (11) | 0.35667 (9) | −0.22515 (8) | 0.02424 (17) | |
H16A | 0.7379 | 0.4242 | −0.2752 | 0.029* | |
H16B | 0.5613 | 0.3935 | −0.1892 | 0.029* | |
C17 | 0.63573 (12) | 0.27105 (9) | −0.29722 (8) | 0.02506 (17) | |
H17A | 0.5556 | 0.2074 | −0.2455 | 0.030* | |
H17B | 0.7358 | 0.2277 | −0.3235 | 0.030* | |
C18 | 0.58040 (11) | 0.33829 (9) | −0.40639 (8) | 0.02417 (17) | |
H18A | 0.4746 | 0.3743 | −0.3809 | 0.029* | |
H18B | 0.6551 | 0.4066 | −0.4560 | 0.029* | |
C19 | 0.57271 (12) | 0.24580 (9) | −0.47838 (8) | 0.02537 (18) | |
H19A | 0.5075 | 0.1735 | −0.4251 | 0.030* | |
H19B | 0.6809 | 0.2157 | −0.5082 | 0.030* | |
C20 | 0.50411 (11) | 0.29821 (9) | −0.58370 (8) | 0.02291 (16) | |
H20A | 0.3978 | 0.3323 | −0.5557 | 0.027* | |
H20B | 0.5730 | 0.3666 | −0.6408 | 0.027* | |
C21 | 0.49168 (11) | 0.19692 (9) | −0.64525 (8) | 0.02409 (17) | |
H21A | 0.4292 | 0.1263 | −0.5861 | 0.029* | |
H21B | 0.5993 | 0.1665 | −0.6763 | 0.029* | |
C22 | 0.41473 (11) | 0.24020 (8) | −0.74698 (8) | 0.02339 (17) | |
H22A | 0.4848 | 0.3026 | −0.8115 | 0.028* | |
H22B | 0.3129 | 0.2806 | −0.7190 | 0.028* | |
C23 | 0.38450 (12) | 0.13207 (9) | −0.79502 (8) | 0.02553 (18) | |
H23A | 0.4858 | 0.0898 | −0.8200 | 0.031* | |
H23B | 0.3116 | 0.0712 | −0.7310 | 0.031* | |
C24 | 0.31312 (12) | 0.17379 (10) | −0.89953 (9) | 0.02908 (19) | |
H24A | 0.3923 | 0.2250 | −0.9676 | 0.035* | |
H24B | 0.2199 | 0.2261 | −0.8785 | 0.035* | |
C25 | 0.26215 (14) | 0.06325 (11) | −0.93513 (10) | 0.0364 (2) | |
H25A | 0.2134 | 0.0949 | −0.9987 | 0.055* | |
H25B | 0.1857 | 0.0109 | −0.8676 | 0.055* | |
H25C | 0.3552 | 0.0143 | −0.9615 | 0.055* | |
H1O1 | 0.9937 (19) | 0.6709 (15) | 0.5747 (15) | 0.054 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0556 (5) | 0.0212 (3) | 0.0321 (4) | 0.0096 (3) | −0.0303 (3) | −0.0091 (3) |
O2 | 0.0347 (3) | 0.0214 (3) | 0.0252 (3) | 0.0039 (2) | −0.0166 (3) | −0.0073 (2) |
O3 | 0.0373 (4) | 0.0246 (3) | 0.0235 (3) | 0.0037 (3) | −0.0170 (3) | −0.0099 (2) |
C1 | 0.0322 (4) | 0.0187 (4) | 0.0236 (4) | 0.0014 (3) | −0.0130 (3) | −0.0042 (3) |
C2 | 0.0410 (5) | 0.0178 (4) | 0.0316 (5) | 0.0032 (3) | −0.0178 (4) | −0.0049 (3) |
C3 | 0.0368 (5) | 0.0178 (4) | 0.0343 (5) | 0.0028 (3) | −0.0164 (4) | −0.0082 (3) |
C4 | 0.0310 (4) | 0.0204 (4) | 0.0287 (4) | 0.0026 (3) | −0.0143 (3) | −0.0100 (3) |
C5 | 0.0247 (4) | 0.0178 (3) | 0.0240 (4) | 0.0031 (3) | −0.0112 (3) | −0.0058 (3) |
C6 | 0.0220 (4) | 0.0171 (3) | 0.0198 (3) | 0.0004 (3) | −0.0084 (3) | −0.0047 (3) |
C7 | 0.0249 (4) | 0.0171 (3) | 0.0216 (4) | 0.0016 (3) | −0.0092 (3) | −0.0055 (3) |
C8 | 0.0273 (4) | 0.0179 (3) | 0.0209 (4) | −0.0003 (3) | −0.0104 (3) | −0.0045 (3) |
C9 | 0.0203 (3) | 0.0191 (3) | 0.0188 (3) | −0.0006 (3) | −0.0068 (3) | −0.0052 (3) |
C10 | 0.0205 (3) | 0.0181 (3) | 0.0172 (3) | −0.0011 (3) | −0.0063 (3) | −0.0044 (3) |
C11 | 0.0247 (4) | 0.0188 (3) | 0.0207 (4) | 0.0014 (3) | −0.0100 (3) | −0.0054 (3) |
C12 | 0.0291 (4) | 0.0196 (4) | 0.0220 (4) | 0.0021 (3) | −0.0114 (3) | −0.0073 (3) |
C13 | 0.0240 (4) | 0.0225 (4) | 0.0182 (3) | −0.0006 (3) | −0.0076 (3) | −0.0066 (3) |
C14 | 0.0259 (4) | 0.0211 (4) | 0.0206 (4) | 0.0019 (3) | −0.0102 (3) | −0.0055 (3) |
C15 | 0.0252 (4) | 0.0187 (3) | 0.0197 (3) | 0.0007 (3) | −0.0083 (3) | −0.0052 (3) |
C16 | 0.0285 (4) | 0.0271 (4) | 0.0210 (4) | 0.0023 (3) | −0.0114 (3) | −0.0085 (3) |
C17 | 0.0295 (4) | 0.0281 (4) | 0.0221 (4) | −0.0002 (3) | −0.0114 (3) | −0.0093 (3) |
C18 | 0.0263 (4) | 0.0281 (4) | 0.0218 (4) | 0.0012 (3) | −0.0100 (3) | −0.0093 (3) |
C19 | 0.0302 (4) | 0.0279 (4) | 0.0216 (4) | 0.0011 (3) | −0.0103 (3) | −0.0092 (3) |
C20 | 0.0246 (4) | 0.0263 (4) | 0.0197 (4) | −0.0002 (3) | −0.0079 (3) | −0.0073 (3) |
C21 | 0.0289 (4) | 0.0260 (4) | 0.0207 (4) | 0.0016 (3) | −0.0110 (3) | −0.0077 (3) |
C22 | 0.0264 (4) | 0.0243 (4) | 0.0219 (4) | 0.0015 (3) | −0.0102 (3) | −0.0068 (3) |
C23 | 0.0316 (4) | 0.0254 (4) | 0.0239 (4) | 0.0023 (3) | −0.0144 (3) | −0.0070 (3) |
C24 | 0.0330 (5) | 0.0309 (5) | 0.0279 (4) | 0.0006 (4) | −0.0176 (4) | −0.0056 (4) |
C25 | 0.0427 (6) | 0.0421 (6) | 0.0349 (5) | 0.0011 (5) | −0.0217 (4) | −0.0156 (5) |
O1—C5 | 1.3523 (10) | C16—C17 | 1.5146 (12) |
O1—H1O1 | 0.943 (17) | C16—H16A | 0.9700 |
O2—C9 | 1.2389 (10) | C16—H16B | 0.9700 |
O3—C13 | 1.3485 (10) | C17—C18 | 1.5260 (13) |
O3—C16 | 1.4363 (11) | C17—H17A | 0.9700 |
C1—C2 | 1.3811 (13) | C17—H17B | 0.9700 |
C1—C6 | 1.4000 (12) | C18—C19 | 1.5236 (12) |
C1—H1A | 0.9300 | C18—H18A | 0.9700 |
C2—C3 | 1.3938 (14) | C18—H18B | 0.9700 |
C2—H2A | 0.9300 | C19—C20 | 1.5239 (13) |
C3—C4 | 1.3846 (13) | C19—H19A | 0.9700 |
C3—H3A | 0.9300 | C19—H19B | 0.9700 |
C4—C5 | 1.3985 (12) | C20—C21 | 1.5228 (12) |
C4—H4A | 0.9300 | C20—H20A | 0.9700 |
C5—C6 | 1.4080 (12) | C20—H20B | 0.9700 |
C6—C7 | 1.4579 (11) | C21—C22 | 1.5229 (12) |
C7—C8 | 1.3414 (12) | C21—H21A | 0.9700 |
C7—H7A | 0.9300 | C21—H21B | 0.9700 |
C8—C9 | 1.4706 (12) | C22—C23 | 1.5250 (13) |
C8—H8A | 0.9300 | C22—H22A | 0.9700 |
C9—C10 | 1.4854 (11) | C22—H22B | 0.9700 |
C10—C15 | 1.3998 (11) | C23—C24 | 1.5201 (13) |
C10—C11 | 1.4072 (12) | C23—H23A | 0.9700 |
C11—C12 | 1.3800 (12) | C23—H23B | 0.9700 |
C11—H11A | 0.9300 | C24—C25 | 1.5252 (15) |
C12—C13 | 1.3999 (12) | C24—H24A | 0.9700 |
C12—H12A | 0.9300 | C24—H24B | 0.9700 |
C13—C14 | 1.3988 (12) | C25—H25A | 0.9600 |
C14—C15 | 1.3906 (12) | C25—H25B | 0.9600 |
C14—H14A | 0.9300 | C25—H25C | 0.9600 |
C15—H15A | 0.9300 | ||
C5—O1—H1O1 | 110.9 (10) | C16—C17—H17A | 108.6 |
C13—O3—C16 | 120.53 (7) | C18—C17—H17A | 108.6 |
C2—C1—C6 | 121.51 (9) | C16—C17—H17B | 108.6 |
C2—C1—H1A | 119.2 | C18—C17—H17B | 108.6 |
C6—C1—H1A | 119.2 | H17A—C17—H17B | 107.6 |
C1—C2—C3 | 119.86 (9) | C19—C18—C17 | 110.31 (8) |
C1—C2—H2A | 120.1 | C19—C18—H18A | 109.6 |
C3—C2—H2A | 120.1 | C17—C18—H18A | 109.6 |
C4—C3—C2 | 120.20 (9) | C19—C18—H18B | 109.6 |
C4—C3—H3A | 119.9 | C17—C18—H18B | 109.6 |
C2—C3—H3A | 119.9 | H18A—C18—H18B | 108.1 |
C3—C4—C5 | 119.80 (8) | C18—C19—C20 | 115.59 (8) |
C3—C4—H4A | 120.1 | C18—C19—H19A | 108.4 |
C5—C4—H4A | 120.1 | C20—C19—H19A | 108.4 |
O1—C5—C4 | 122.25 (8) | C18—C19—H19B | 108.4 |
O1—C5—C6 | 116.99 (8) | C20—C19—H19B | 108.4 |
C4—C5—C6 | 120.76 (8) | H19A—C19—H19B | 107.4 |
C1—C6—C5 | 117.86 (8) | C21—C20—C19 | 111.70 (8) |
C1—C6—C7 | 122.86 (8) | C21—C20—H20A | 109.3 |
C5—C6—C7 | 119.27 (7) | C19—C20—H20A | 109.3 |
C8—C7—C6 | 126.24 (8) | C21—C20—H20B | 109.3 |
C8—C7—H7A | 116.9 | C19—C20—H20B | 109.3 |
C6—C7—H7A | 116.9 | H20A—C20—H20B | 107.9 |
C7—C8—C9 | 122.90 (8) | C20—C21—C22 | 114.80 (8) |
C7—C8—H8A | 118.6 | C20—C21—H21A | 108.6 |
C9—C8—H8A | 118.6 | C22—C21—H21A | 108.6 |
O2—C9—C8 | 122.21 (8) | C20—C21—H21B | 108.6 |
O2—C9—C10 | 119.06 (7) | C22—C21—H21B | 108.6 |
C8—C9—C10 | 118.72 (7) | H21A—C21—H21B | 107.5 |
C15—C10—C11 | 117.94 (8) | C21—C22—C23 | 112.95 (7) |
C15—C10—C9 | 124.00 (7) | C21—C22—H22A | 109.0 |
C11—C10—C9 | 118.06 (7) | C23—C22—H22A | 109.0 |
C12—C11—C10 | 121.04 (8) | C21—C22—H22B | 109.0 |
C12—C11—H11A | 119.5 | C23—C22—H22B | 109.0 |
C10—C11—H11A | 119.5 | H22A—C22—H22B | 107.8 |
C11—C12—C13 | 120.15 (8) | C24—C23—C22 | 113.85 (8) |
C11—C12—H12A | 119.9 | C24—C23—H23A | 108.8 |
C13—C12—H12A | 119.9 | C22—C23—H23A | 108.8 |
O3—C13—C14 | 125.19 (8) | C24—C23—H23B | 108.8 |
O3—C13—C12 | 114.85 (8) | C22—C23—H23B | 108.8 |
C14—C13—C12 | 119.96 (8) | H23A—C23—H23B | 107.7 |
C15—C14—C13 | 119.15 (8) | C23—C24—C25 | 113.04 (8) |
C15—C14—H14A | 120.4 | C23—C24—H24A | 109.0 |
C13—C14—H14A | 120.4 | C25—C24—H24A | 109.0 |
C14—C15—C10 | 121.76 (8) | C23—C24—H24B | 109.0 |
C14—C15—H15A | 119.1 | C25—C24—H24B | 109.0 |
C10—C15—H15A | 119.1 | H24A—C24—H24B | 107.8 |
O3—C16—C17 | 104.98 (7) | C24—C25—H25A | 109.5 |
O3—C16—H16A | 110.8 | C24—C25—H25B | 109.5 |
C17—C16—H16A | 110.8 | H25A—C25—H25B | 109.5 |
O3—C16—H16B | 110.8 | C24—C25—H25C | 109.5 |
C17—C16—H16B | 110.8 | H25A—C25—H25C | 109.5 |
H16A—C16—H16B | 108.8 | H25B—C25—H25C | 109.5 |
C16—C17—C18 | 114.77 (8) | ||
C6—C1—C2—C3 | 0.50 (15) | C9—C10—C11—C12 | 179.29 (7) |
C1—C2—C3—C4 | −0.91 (16) | C10—C11—C12—C13 | −0.32 (13) |
C2—C3—C4—C5 | 0.14 (15) | C16—O3—C13—C14 | 4.73 (13) |
C3—C4—C5—O1 | −178.52 (9) | C16—O3—C13—C12 | −175.05 (8) |
C3—C4—C5—C6 | 1.05 (14) | C11—C12—C13—O3 | −179.37 (8) |
C2—C1—C6—C5 | 0.65 (14) | C11—C12—C13—C14 | 0.84 (13) |
C2—C1—C6—C7 | 179.81 (9) | O3—C13—C14—C15 | 179.56 (8) |
O1—C5—C6—C1 | 178.17 (8) | C12—C13—C14—C15 | −0.67 (13) |
C4—C5—C6—C1 | −1.42 (13) | C13—C14—C15—C10 | −0.01 (13) |
O1—C5—C6—C7 | −1.02 (12) | C11—C10—C15—C14 | 0.51 (13) |
C4—C5—C6—C7 | 179.39 (8) | C9—C10—C15—C14 | −179.10 (8) |
C1—C6—C7—C8 | 4.99 (14) | C13—O3—C16—C17 | −179.02 (7) |
C5—C6—C7—C8 | −175.86 (9) | O3—C16—C17—C18 | −175.00 (7) |
C6—C7—C8—C9 | 179.01 (8) | C16—C17—C18—C19 | 174.72 (8) |
C7—C8—C9—O2 | −6.40 (14) | C17—C18—C19—C20 | 174.57 (8) |
C7—C8—C9—C10 | 173.90 (8) | C18—C19—C20—C21 | −176.48 (7) |
O2—C9—C10—C15 | 173.99 (8) | C19—C20—C21—C22 | 176.53 (8) |
C8—C9—C10—C15 | −6.30 (12) | C20—C21—C22—C23 | −172.41 (8) |
O2—C9—C10—C11 | −5.62 (12) | C21—C22—C23—C24 | −177.98 (8) |
C8—C9—C10—C11 | 174.09 (7) | C22—C23—C24—C25 | −172.02 (9) |
C15—C10—C11—C12 | −0.34 (13) |
Cg1 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2i | 0.939 (18) | 1.789 (18) | 2.6867 (12) | 159.0 (16) |
C7—H7A···O1i | 0.93 | 2.31 | 3.2169 (13) | 164 |
C22—H22A···Cg1ii | 0.97 | 2.85 | 3.6887 (12) | 146 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C25H32O3 |
Mr | 380.51 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.6674 (13), 10.9865 (17), 12.1352 (19) |
α, β, γ (°) | 74.405 (3), 72.891 (3), 85.981 (4) |
V (Å3) | 1063.7 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.62 × 0.15 × 0.14 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.955, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30192, 8434, 6213 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.784 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.160, 1.02 |
No. of reflections | 8434 |
No. of parameters | 258 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.63, −0.20 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2i | 0.939 (18) | 1.789 (18) | 2.6867 (12) | 159.0 (16) |
C7—H7A···O1i | 0.9300 | 2.3100 | 3.2169 (13) | 164.00 |
C22—H22A···Cg1ii | 0.9700 | 2.85 | 3.6887 (12) | 146 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y, z−1. |
Footnotes
‡Thomson Reuters ResearcherID: A-5599-2009.
Acknowledgements
IAR and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171. ZN and HH thank Universiti Malaysia Sarawak and the Ministry of Science, Technology and Innovation (MOSTI), for financing this project through FRGS/01(14)/743/2010 (29). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.
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Chalcones have displayed an impressive array of biological activities and are extensively reported (Xue et al., 2004; Bhat et al., 2005; Won et al., 2005; Zhao et al., 2005 and Satyanarayana et al., 2004). Here in, we report the crystal structure of the title compound (I).
In (I), Fig. 1, the bond lengths observed are comparable with standard reported values (Allen et al., 1987). The enone (O2/C7–C9) moiety adopts a s-cis conformation with a torsion angle of -6.41 (15)°. The mean plane through the enone (O2/C7–C9) moiety form dihedral angles of 2.80 (6) and 7.26 (6)° respectively with the benzene (C1–C6 and C10–C15) rings. The dihedral angle between the two benzene rings is 7.86 (5)°.
An observed widening of the C1–C6–C7 and C6–C7–C8 angles of 122.85 (8) and 126.23 (8)° respectively, may be the consequence of the short contact between H1A and H8A (2.19 Å). Similarly, the slight distortion of the O3–C13–C14 angle to 125.18 (9)° may be the result of a close H14A and H16B (2.37 Å) contact. The geometric parameters are consistent to those observed in closely related structures (Razak et al., 2009; Ngaini et al., 2010; Ngaini et al., 2011).
The alkoxy chain adopts an all trans conformation with the difference from the ideal values of the torsion angles ranging from 0.98 (7)° to 7.98 (9)°. The C16–O3–C13–C14 torsion angle of 4.73 (13)° indicate that atoms C16 and O3 and the attached benzene ring are approximately co-planar. The alkoxy chain appears to deviate from co-planarity with the ring for atoms further away i.e. C24 and C25. The dihedral angle between the least-square plane through atoms O3/C16–C25 [maximum deviation = 0.2507 (10)Å at C25] and the attached benzene ring is 15.20 (5)°.
In the crystal (Fig. 2), molecules are connected by a pair of O1—H1O1···O2i and a pair of weak C7—H7A···O1i hydrogen bonds to form a R22(10) ring and two R22(7) rings within inversion dimers. These dimers are arranged into sheets parallel to (201). Weak C—H···π interactions (Table 1) are also observed.