organic compounds
1-(3,4-Dimethoxyphenyl)-3-phenylprop-2-en-1-one
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title compound, C17H16O3, the dihedral angle between the mean planes of the benzene rings is 57.1 (1)°. The mean plane of the ketone group is twisted by 10.0 (5)° from that of the dimethoxyphenyl ring. The two dimethoxyphenyl groups are twisted slighly from the mean plane of the phenyl ring, with C—O—C—C torsion angles of 6.4 (2) and −7.9 (2)° [r.m.s. deviations = 0.15 (3) and 0.18 (3) Å for the two methoxy C atoms]. In the crystal, weak centroid–centroid π–π stacking interactions, with intercentroid distances of 3.8939 (11) and 3.9430 (10) Å are observed.
CCDC reference: 987727
Related literature
For applications of the title compound as an intermediate in the synthesis of pyrazole derivatives, which have pharmaceutical applications, see: Basavaraju & Devaraju (2002). For applications of chalcone derivatives in biological studies, see: Choudhary & Juyal (2011). For applications of chalcone derivatives for their blue-light transmittance, see: Uchida et al. (1998). For the synthesis, see: Umesha & Basavaraju (2013). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 987727
10.1107/S160053681400378X/bt6962sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681400378X/bt6962Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681400378X/bt6962Isup3.cml
1-(3,4-Dimethoxyphenyl)ethanone (1.80 g 10 mmol) and benzaldehyde (1.02 ml, 10 mmol) were stirred in water (40 ml) and ethanol (20 ml) mixture in the presence of sodium hydroxide (0.8 g, 20 mmol) at 288–303 K for 4 h (Fig. 2). The reaction mixture was kept overnight in an ice bath. The precipitated products were filtered and recrystallized from methanol. Anal. calcd. for C17H16O3: C, 76.10; H, 6.01. Found: C, 76.04; H, 5.89% (Umesha & Basavaraju, 2013).
All of the H atoms were placed in their calculated positions and then refined using the riding model with C—H lengths of 0.95 Å (CH) or 0.98 Å (CH3). Isotropic displacement parameters for these atoms were set to 1.2 (CH) or 1.5 (CH3) times Ueq of the parent atom. Idealized Me were refined as a rotating group.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. ORTEP drawing of (I), C17H16O3, showing the labeling scheme with 50% probability displacement ellipsoids. | |
Fig. 2. The formation of the title compound. |
C17H16O3 | Z = 2 |
Mr = 268.30 | F(000) = 284 |
Triclinic, P1 | Dx = 1.278 Mg m−3 |
a = 7.3269 (7) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.8923 (11) Å | Cell parameters from 1960 reflections |
c = 10.7668 (11) Å | θ = 4.5–72.3° |
α = 102.408 (9)° | µ = 0.70 mm−1 |
β = 109.255 (9)° | T = 173 K |
γ = 98.951 (9)° | Irregular, orange |
V = 697.48 (13) Å3 | 0.36 × 0.28 × 0.16 mm |
Agilent Xcalibur (Eos, Gemini) diffractometer | 2671 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2261 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 72.4°, θmin = 4.5° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | k = −11→12 |
Tmin = 0.842, Tmax = 1.000 | l = −12→13 |
4094 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0909P)2 + 0.0371P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.152 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.30 e Å−3 |
2671 reflections | Δρmin = −0.20 e Å−3 |
184 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.016 (3) |
Primary atom site location: structure-invariant direct methods |
C17H16O3 | γ = 98.951 (9)° |
Mr = 268.30 | V = 697.48 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3269 (7) Å | Cu Kα radiation |
b = 9.8923 (11) Å | µ = 0.70 mm−1 |
c = 10.7668 (11) Å | T = 173 K |
α = 102.408 (9)° | 0.36 × 0.28 × 0.16 mm |
β = 109.255 (9)° |
Agilent Xcalibur (Eos, Gemini) diffractometer | 2671 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 2261 reflections with I > 2σ(I) |
Tmin = 0.842, Tmax = 1.000 | Rint = 0.034 |
4094 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.30 e Å−3 |
2671 reflections | Δρmin = −0.20 e Å−3 |
184 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1915 (2) | 0.40453 (12) | 0.63226 (11) | 0.0458 (4) | |
O2 | 0.11843 (19) | 0.13233 (12) | 0.97010 (11) | 0.0408 (3) | |
O3 | 0.17608 (19) | 0.32198 (13) | 1.19243 (11) | 0.0412 (3) | |
C1 | 0.2507 (2) | 0.49627 (17) | 0.74331 (15) | 0.0340 (4) | |
C2 | 0.3317 (2) | 0.64736 (17) | 0.75594 (16) | 0.0354 (4) | |
H2 | 0.4221 | 0.7092 | 0.8425 | 0.042* | |
C3 | 0.2797 (2) | 0.69778 (17) | 0.64760 (15) | 0.0349 (4) | |
H3 | 0.1903 | 0.6322 | 0.5627 | 0.042* | |
C4 | 0.3472 (2) | 0.84500 (16) | 0.64690 (15) | 0.0335 (4) | |
C5 | 0.2255 (3) | 0.89601 (17) | 0.54684 (16) | 0.0379 (4) | |
H5 | 0.1058 | 0.8340 | 0.4781 | 0.046* | |
C6 | 0.2791 (3) | 1.03693 (18) | 0.54759 (17) | 0.0426 (4) | |
H6 | 0.1942 | 1.0718 | 0.4806 | 0.051* | |
C7 | 0.4548 (3) | 1.12685 (18) | 0.64490 (18) | 0.0439 (4) | |
H7 | 0.4906 | 1.2234 | 0.6450 | 0.053* | |
C8 | 0.5793 (3) | 1.07642 (18) | 0.74269 (17) | 0.0423 (4) | |
H8 | 0.7013 | 1.1381 | 0.8089 | 0.051* | |
C9 | 0.5262 (2) | 0.93635 (17) | 0.74404 (16) | 0.0375 (4) | |
H9 | 0.6118 | 0.9022 | 0.8113 | 0.045* | |
C10 | 0.2372 (2) | 0.45707 (16) | 0.86635 (15) | 0.0315 (4) | |
C11 | 0.2692 (2) | 0.55923 (17) | 0.98761 (16) | 0.0349 (4) | |
H11 | 0.3050 | 0.6579 | 0.9945 | 0.042* | |
C12 | 0.2489 (2) | 0.51738 (17) | 1.09853 (15) | 0.0361 (4) | |
H12 | 0.2698 | 0.5877 | 1.1807 | 0.043* | |
C13 | 0.1986 (2) | 0.37465 (17) | 1.09029 (15) | 0.0335 (4) | |
C14 | 0.1668 (2) | 0.26993 (17) | 0.96737 (15) | 0.0322 (4) | |
C15 | 0.1855 (2) | 0.31230 (16) | 0.85772 (14) | 0.0318 (4) | |
H15 | 0.1630 | 0.2423 | 0.7750 | 0.038* | |
C16 | 0.1048 (3) | 0.02320 (18) | 0.85413 (17) | 0.0456 (5) | |
H16A | −0.0049 | 0.0246 | 0.7726 | 0.068* | |
H16B | 0.0797 | −0.0701 | 0.8711 | 0.068* | |
H16C | 0.2303 | 0.0402 | 0.8391 | 0.068* | |
C17 | 0.2323 (3) | 0.4222 (2) | 1.32445 (16) | 0.0475 (5) | |
H17A | 0.1481 | 0.4902 | 1.3175 | 0.071* | |
H17B | 0.3723 | 0.4738 | 1.3562 | 0.071* | |
H17C | 0.2151 | 0.3711 | 1.3899 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0689 (9) | 0.0374 (6) | 0.0314 (6) | 0.0090 (6) | 0.0214 (6) | 0.0095 (5) |
O2 | 0.0594 (8) | 0.0336 (6) | 0.0330 (6) | 0.0083 (5) | 0.0237 (5) | 0.0092 (5) |
O3 | 0.0523 (7) | 0.0461 (7) | 0.0281 (6) | 0.0104 (5) | 0.0194 (5) | 0.0106 (5) |
C1 | 0.0356 (8) | 0.0368 (8) | 0.0314 (8) | 0.0102 (6) | 0.0135 (6) | 0.0106 (6) |
C2 | 0.0359 (8) | 0.0376 (9) | 0.0319 (8) | 0.0070 (6) | 0.0134 (6) | 0.0092 (6) |
C3 | 0.0385 (8) | 0.0343 (8) | 0.0316 (7) | 0.0085 (6) | 0.0145 (6) | 0.0068 (6) |
C4 | 0.0388 (8) | 0.0342 (8) | 0.0310 (7) | 0.0108 (6) | 0.0173 (6) | 0.0085 (6) |
C5 | 0.0416 (9) | 0.0390 (9) | 0.0313 (8) | 0.0092 (7) | 0.0124 (6) | 0.0088 (6) |
C6 | 0.0504 (10) | 0.0417 (9) | 0.0383 (9) | 0.0158 (7) | 0.0152 (7) | 0.0156 (7) |
C7 | 0.0540 (10) | 0.0326 (8) | 0.0486 (9) | 0.0113 (7) | 0.0233 (8) | 0.0116 (7) |
C8 | 0.0388 (9) | 0.0385 (9) | 0.0432 (9) | 0.0048 (7) | 0.0130 (7) | 0.0060 (7) |
C9 | 0.0377 (9) | 0.0390 (9) | 0.0362 (8) | 0.0109 (7) | 0.0133 (7) | 0.0117 (6) |
C10 | 0.0305 (7) | 0.0362 (8) | 0.0285 (7) | 0.0090 (6) | 0.0117 (6) | 0.0090 (6) |
C11 | 0.0351 (8) | 0.0332 (8) | 0.0340 (8) | 0.0060 (6) | 0.0128 (6) | 0.0068 (6) |
C12 | 0.0373 (8) | 0.0386 (9) | 0.0287 (7) | 0.0085 (7) | 0.0131 (6) | 0.0017 (6) |
C13 | 0.0330 (8) | 0.0409 (8) | 0.0271 (7) | 0.0084 (6) | 0.0132 (6) | 0.0085 (6) |
C14 | 0.0317 (8) | 0.0356 (8) | 0.0288 (7) | 0.0077 (6) | 0.0116 (6) | 0.0084 (6) |
C15 | 0.0325 (8) | 0.0362 (8) | 0.0254 (7) | 0.0081 (6) | 0.0111 (6) | 0.0060 (6) |
C16 | 0.0664 (12) | 0.0332 (8) | 0.0426 (9) | 0.0097 (8) | 0.0303 (9) | 0.0079 (7) |
C17 | 0.0549 (11) | 0.0619 (11) | 0.0258 (8) | 0.0141 (9) | 0.0185 (7) | 0.0078 (7) |
O1—C1 | 1.2290 (18) | C8—H8 | 0.9500 |
O2—C14 | 1.3613 (19) | C8—C9 | 1.384 (2) |
O2—C16 | 1.4282 (18) | C9—H9 | 0.9500 |
O3—C13 | 1.3592 (18) | C10—C11 | 1.392 (2) |
O3—C17 | 1.4331 (19) | C10—C15 | 1.398 (2) |
C1—C2 | 1.479 (2) | C11—H11 | 0.9500 |
C1—C10 | 1.487 (2) | C11—C12 | 1.389 (2) |
C2—H2 | 0.9500 | C12—H12 | 0.9500 |
C2—C3 | 1.331 (2) | C12—C13 | 1.378 (2) |
C3—H3 | 0.9500 | C13—C14 | 1.418 (2) |
C3—C4 | 1.466 (2) | C14—C15 | 1.375 (2) |
C4—C5 | 1.396 (2) | C15—H15 | 0.9500 |
C4—C9 | 1.397 (2) | C16—H16A | 0.9800 |
C5—H5 | 0.9500 | C16—H16B | 0.9800 |
C5—C6 | 1.386 (2) | C16—H16C | 0.9800 |
C6—H6 | 0.9500 | C17—H17A | 0.9800 |
C6—C7 | 1.378 (3) | C17—H17B | 0.9800 |
C7—H7 | 0.9500 | C17—H17C | 0.9800 |
C7—C8 | 1.387 (2) | ||
C14—O2—C16 | 117.05 (12) | C11—C10—C15 | 119.33 (14) |
C13—O3—C17 | 117.20 (13) | C15—C10—C1 | 118.37 (13) |
O1—C1—C2 | 120.69 (14) | C10—C11—H11 | 119.9 |
O1—C1—C10 | 120.23 (14) | C12—C11—C10 | 120.20 (15) |
C2—C1—C10 | 119.06 (13) | C12—C11—H11 | 119.9 |
C1—C2—H2 | 119.6 | C11—C12—H12 | 119.7 |
C3—C2—C1 | 120.82 (14) | C13—C12—C11 | 120.51 (14) |
C3—C2—H2 | 119.6 | C13—C12—H12 | 119.7 |
C2—C3—H3 | 116.9 | O3—C13—C12 | 125.41 (14) |
C2—C3—C4 | 126.11 (14) | O3—C13—C14 | 114.96 (14) |
C4—C3—H3 | 116.9 | C12—C13—C14 | 119.63 (14) |
C5—C4—C3 | 118.50 (14) | O2—C14—C13 | 114.95 (13) |
C5—C4—C9 | 119.08 (15) | O2—C14—C15 | 125.58 (14) |
C9—C4—C3 | 122.41 (14) | C15—C14—C13 | 119.47 (14) |
C4—C5—H5 | 119.9 | C10—C15—H15 | 119.6 |
C6—C5—C4 | 120.12 (15) | C14—C15—C10 | 120.86 (14) |
C6—C5—H5 | 119.9 | C14—C15—H15 | 119.6 |
C5—C6—H6 | 119.8 | O2—C16—H16A | 109.5 |
C7—C6—C5 | 120.37 (16) | O2—C16—H16B | 109.5 |
C7—C6—H6 | 119.8 | O2—C16—H16C | 109.5 |
C6—C7—H7 | 120.0 | H16A—C16—H16B | 109.5 |
C6—C7—C8 | 120.02 (16) | H16A—C16—H16C | 109.5 |
C8—C7—H7 | 120.0 | H16B—C16—H16C | 109.5 |
C7—C8—H8 | 119.9 | O3—C17—H17A | 109.5 |
C9—C8—C7 | 120.13 (16) | O3—C17—H17B | 109.5 |
C9—C8—H8 | 119.9 | O3—C17—H17C | 109.5 |
C4—C9—H9 | 119.9 | H17A—C17—H17B | 109.5 |
C8—C9—C4 | 120.23 (15) | H17A—C17—H17C | 109.5 |
C8—C9—H9 | 119.9 | H17B—C17—H17C | 109.5 |
C11—C10—C1 | 122.28 (14) | ||
O1—C1—C2—C3 | 24.6 (2) | C5—C6—C7—C8 | 0.1 (3) |
O1—C1—C10—C11 | −168.54 (15) | C6—C7—C8—C9 | −0.9 (3) |
O1—C1—C10—C15 | 9.7 (2) | C7—C8—C9—C4 | 0.1 (3) |
O2—C14—C15—C10 | −179.58 (14) | C9—C4—C5—C6 | −2.3 (2) |
O3—C13—C14—O2 | 0.0 (2) | C10—C1—C2—C3 | −153.98 (15) |
O3—C13—C14—C15 | 179.85 (13) | C10—C11—C12—C13 | 0.5 (2) |
C1—C2—C3—C4 | 179.22 (14) | C11—C10—C15—C14 | −0.3 (2) |
C1—C10—C11—C12 | 178.00 (14) | C11—C12—C13—O3 | 179.57 (15) |
C1—C10—C15—C14 | −178.63 (13) | C11—C12—C13—C14 | −0.2 (2) |
C2—C1—C10—C11 | 10.0 (2) | C12—C13—C14—O2 | 179.81 (14) |
C2—C1—C10—C15 | −171.68 (13) | C12—C13—C14—C15 | −0.4 (2) |
C2—C3—C4—C5 | −154.28 (17) | C13—C14—C15—C10 | 0.6 (2) |
C2—C3—C4—C9 | 24.4 (2) | C15—C10—C11—C12 | −0.3 (2) |
C3—C4—C5—C6 | 176.43 (15) | C16—O2—C14—C13 | −173.81 (14) |
C3—C4—C9—C8 | −177.18 (15) | C16—O2—C14—C15 | 6.4 (2) |
C4—C5—C6—C7 | 1.5 (3) | C17—O3—C13—C12 | −7.9 (2) |
C5—C4—C9—C8 | 1.5 (2) | C17—O3—C13—C14 | 171.84 (14) |
Experimental details
Crystal data | |
Chemical formula | C17H16O3 |
Mr | 268.30 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 7.3269 (7), 9.8923 (11), 10.7668 (11) |
α, β, γ (°) | 102.408 (9), 109.255 (9), 98.951 (9) |
V (Å3) | 697.48 (13) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.70 |
Crystal size (mm) | 0.36 × 0.28 × 0.16 |
Data collection | |
Diffractometer | Agilent Xcalibur (Eos, Gemini) diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) |
Tmin, Tmax | 0.842, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4094, 2671, 2261 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.152, 1.05 |
No. of reflections | 2671 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.20 |
Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis RED (Agilent, 2012), SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
References
Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
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. CSD CrossRef Web of Science Google Scholar
Basavaraju, Y. B. & Devaraju (2002). Indian J. Heterocycl. Chem. 11, 229–232. Google Scholar
Choudhary, A. N. & Juyal, V. (2011). Int. J. Pharm. Pharm. Sci. 3, 125–128. CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575–580. Web of Science CrossRef CAS IUCr Journals Google Scholar
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975–984. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140. Web of Science CrossRef Google Scholar
Umesha, B. & Basavaraju, Y. B. (2013). Eur. J. Chem. 4, 235–239. CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
1-(3,4-dimethoxyphenyl)-3-phenylprop-2-en-1-one is an intermediate for the synthesis of pyrazole derivatives, podophyllotoxin and its derivatives which have pharmaceutical applications (Basavaraju & Devaraju, 2002). More generally, chalcone derivatives have many applications in biological studies (Choudhary & Juyal, 2011). Chalcone derivatives are notable for their excellent blue-light transmittance and good crystallizability (Uchida et al., 1998). In continuation of our work on chalcone derivatives, this paper reports the crystal structure of the title compound C17H16O3.
In the title compound the dihedral angle between the mean planes of the two phenyl rings is 57.1 (1)° (Fig. 1). The mean plane of the ketone group (C2/C1/O1/C10) is twisted by 10.0 (5)° from that of the dimethoxyphenyl ring. The two dimethoxyphenyl groups are twisted slighly from the mean plane of the phenyl ring with torsion angles of 6.4 (2)° (C16/O2/C14/C15) and -7.9 (2)° (C17/O3/C13/C12) [r.m.s. deviations = 0.15 (3) and 0.18 (3)Å for the two methoxy C atoms]. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, while no classical hydrogen bonds are observed, weak Cg1–Cg1 and Cg2–Cg2 π–π stacking interactions with intercentroid distances of 3.8939 (11) Å and 3.9430 (10) Å (Symmetry operations 1 - x, 2 - y, 1 - z and -x, 1 - y, 2 - z; Cg1 and Cg2 are the centroids of the phenyl rings, C4–C9 and C10–C15) between the phenyl rings are observed and contribute to the crystal packing.