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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160430
doi:10.1107/S2414314616004302

4-(4-Meth­­oxy­phen­yl)-5,7-di­methyl­chroman-2-one

Jaqueline Evangelista Queiroz,a Giuliana Muniz Vila Verde,a Mariette Miguens Pereira,b Manuela Ramos Silvac and Gilberto L. B. Aquinoa*

aState University of Goias, Br 153 Km 98, 75132-400, Anapolis, GO, Brazil, bDepartment of Chemistry, University of Coimbra, P-3004-535 Coimbra, Portugal, and cCFisUC, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal
*Correspondence e-mail: gilberto.benedito@ueg.br

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 10 March 2016; accepted 14 March 2016; online 18 March 2016)

In the title compound, C18H18O3, a di­hydro­coumarin synthesized via a microwave-assisted hydro­aryl­ation reaction, the 4-meth­oxy­phenyl ring is inclined to the mean plane of the coumarin moiety by 78.21 (9)°. The pyran ring has a screw-boat conformation and its mean plane is inclined to the fused benzene ring by 13.88 (11)°. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming ribbons along the b-axis direction. The ribbons are linked via C—H⋯π inter­actions, forming slabs parallel to the ab plane.

CCDC reference: 1465266

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Coumarin derivatives exist widely in nature, especially in plants (Asai et al., 1991[Asai, F., Iinuma, M., Tanaka, T. & Mizuno, M. (1991). Phytochemistry, 30, 3091-3093.]), and show a wide range of biological effects such as anti-inflammatory, anti-oxidative, anti-ageing and anti-cancer activities. 4-Aryl-3,4-di­hydro­coumarins are of synthetic inter­est because they are present in a number of natural mol­ecules, such as neoflavonoids and other complex flavonoids. Di­hydro­coumarins may be obtained by methods based on acid-mediated hydro­aryl­ation of alkenes (Jagdale & Sudalai, 2007[Jagdale, A. R. & Sudalai, A. (2007). Tetrahedron Lett. 48, 4895-4898.]). However, these methods use toxic solvents and long reaction times. In the present work the hydro­aryl­ation was carried out using microwave irradiation and using tri­fluoro­acetic acid as solvent. The simplicity of this approach makes it particularly attractive for use in combinatorial synthesis. Herein we report on the synthesis and crystal structure of the title di­hydro­coumarin compound.

The title compound, Fig. 1[link], is L-shaped with the 4-meth­oxy­phenyl ring being inclined to the mean plane of the coumarin moiety by 78.21 (9)°. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds (Table 1[link] and Fig. 2[link]), forming ribbons along [010]. The ribbons are linked by C—H⋯π inter­actions, forming slabs parallel to (001); see Fig. 2[link] and Table 1[link].

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12–C17 benzene ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2B⋯O3i 0.97 2.52 3.327 (3) 140
C3—H3⋯O2ii 0.98 2.53 3.446 (3) 156
C6—H6⋯Cg3iii 0.93 2.95 3.853 (3) 165
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) x, y-1, z; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids.
[Figure 2]
Figure 2
A view along the b axis of thec crystal packing of the title compound, showing the C—H⋯O hydrogen bonds as dashed lines, and with the C—H⋯π inter­actions represented by thin blue lines. Details are given in Table 1[link] and H atoms not involved in these inter­actions have been omitted for clarity.

Synthesis and crystallization

A mixture of 3,5-dimethyl-phenol (0.245 g, 2.00 mmol) and 4-meth­oxy­cinnamic acid (0.356 g, 2 mmol) was placed in a cylindrical quartz reactor (4 cm diameter). The reactor was then introduced into a CEM Discover microwave reactor [2.45 GHz, adjusted power of 250 W, and an IR temperature detector]. The stirred liquid mixture was irradiated for 5 min at 333 K. The mixture was then allowed to cool and a white solid formed rapidly (< 5 min) at 298 K. This crude solid was filtered off (under nitro­gen), washed with anhydrous ethanol (3 × 5 ml), and vacuum dried for 1 h. The solid was further dried under high vacuum (10−2 Torr) at 298 K for 8 h. Recrystallization from dry ethanol solution gave the title compound as colourless needle-like crystals (yield 65%; m.p. = 413–418 K). 1H NMR (CDCl3, 400 MHz) δ 2.14 (s, 3H); 2.34 (s, 3H); 2.97 (dd, 1H, J = 15.6 and 2.58 Hz); 3.00 (dd, 1H, J = 15.6 and 6.0 Hz); 4.32 (dd, 1H, J = 6.0 and 2.58 Hz); 6.79–6.76 (m, 2H); 6.81–6.80 (m, 2H); 6.96–6.94 (m, 2H). 13C NMR (101 MHz,CDCl3) δ p.p.m. 18.62; 21.08; 37.21; 37.98; 55.25; 114.45; 115.42; 120.47; 127.28; 128.02; 132.32; 136.54; 138.68; 152.03; 158.80; 167.66.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Reflections 1 0 2, 2 0 2, 2 0 0 and 1 1 1 affected by the backstop were removed during the final cycles of refinement.

Table 2
Experimental details

Crystal data
Chemical formula C18H18O3
Mr 282.32
Crystal system, space group Orthorhombic, Pbca
Temperature (K) 293
a, b, c (Å) 16.1115 (19), 7.7040 (9), 23.873 (3)
V (Å3) 2963.2 (6)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.35 × 0.20 × 0.12
 
Data collection
Diffractometer Bruker APEX CCD area-detector
Absorption correction Multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.303, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections 13132, 2786, 1563
Rint 0.070
(sin θ/λ)max (Å−1) 0.610
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.155, 0.97
No. of reflections 2786
No. of parameters 194
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.19, −0.18
Computer programs: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 1465266

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616004302/su4021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004302/su4021Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004302/su4021Isup3.cml

checkCIF report


Experimental top

A mixture of 3,5-dimethyl-phenol (0,245 g, 2,00 mmol) and 4-methoxycinnamic acid (0.356 g, 2 mmol) was placed in a cylindrical quartz reactor (4 cm diameter). The reactor was then introduced into a CEM Discover microwave reactor [2.45 GHz, adjusted power of 250 W, and an IR temperature detector]. The stirred liquid mixture was irradiated for 5 min at 333 K. The mixture was then allowed to cool and a white solid formed rapidly (< 5 min) at 298 K. This crude solid was filtered off (under nitrogen), washed with anhydrous ethanol (3 × 5 ml), and vacuum dried for 1 h. The solid was further dried under high vacuum (10–2 Torr) at 298 K for 8 h. Recrystallization from dry ethanol gave the title compound as colourless needle-like crystals (yield 65%; m.p. = 413–418 K). 1H NMR (CDCl3, 400 MHz) δ 2.14 (s, 3H); 2.34 (s, 3H); 2.97 (dd, 1H, J = 15.6 and 2.58 Hz); 3.00 (dd, 1H, J = 15.6 and 6.0 Hz); 4.32 (dd, 1H, J = 6.0 and 2.58 Hz); 6.79–6.76 (m, 2H); 6.81–6.80 (m, 2H); 6.96–6.94 (m, 2H). 13C NMR (101 MHz,CDCl3) δ p.p.m. 18.62; 21.08; 37.21; 37.98; 55.25; 114.45; 115.42; 120.47; 127.28; 128.02; 132.32; 136.54; 138.68; 152.03; 158.80; 167.66.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Reflections 1 0 2, 2 0 2, 2 0 0 and 1 1 1 affected by the backstop were removed during the final cycles of refinement.

Structure description top

Coumarin derivatives exist widely in nature, especially in plants (Asai et al., 1991), and show a wide range of biological activities such as anti-inflammatory, anti-oxidative, anti-ageing and anti-cancer. 4-Aryl-3,4-dihydrocoumarins are of synthetic interest because they are present in a number of natural molecules, such as neoflavonoids and other complex flavonoids. Dihydrocoumarins may be obtained by methods based on acid-mediated hydroarylation of alkenes (Jagdale & Sudalai, 2007). However, these methods use toxic solvents and long reaction times. In the present work the hydroarylation was carried out using microwave irradiation and using trifluoroacetic acid as solvent. The simplicity of this approach makes it particularly attractive for use in combinatorial synthesis. Herein we report on the synthesis and crystal structure of the title dihydrocoumarin compound.

The title compound, Fig. 1, is L-shaped with the 4-methoxyphenyl ring being inclined to the mean plane of the coumarin moiety by 78.21 (9)°. In the crystal, molecules are linked via C—H···O hydrogen bonds (Table 1 and Fig. 2), forming ribbons along [010]. The ribbons are linked by C—H···π interactions, forming slabs parallel to (001); see Fig. 2 and Table 1.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A view along the b axis of thec crystal packing of the title compound, showing the C—H···O hydrogen bonds as dashed lines, and with the C—H···π interactions represented by thin blue lines. Details are given in Table 1 and H atoms not involved in these interactions have been omitted for clarity.
4-(4-Methoxyphenyl)-5,7-dimethylchroman-2-one top
Crystal data top
C18H18O3Dx = 1.266 Mg m−3
Mr = 282.32Melting point: 418 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 16.1115 (19) ÅCell parameters from 1347 reflections
b = 7.7040 (9) Åθ = 3.1–20.8°
c = 23.873 (3) ŵ = 0.09 mm−1
V = 2963.2 (6) Å3T = 293 K
Z = 8Block, colorless
F(000) = 12000.35 × 0.20 × 0.12 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer		2786 independent reflections
Radiation source: fine-focus sealed tube1563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ and ω scansθmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		h = −17→19
Tmin = 0.303, Tmax = 0.999k = −9→9
13132 measured reflectionsl = −15→29
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0794P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
2786 reflectionsΔρmax = 0.19 e Å−3
194 parametersΔρmin = −0.18 e Å−3
0 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0059 (10)
Crystal data top
C18H18O3V = 2963.2 (6) Å3
Mr = 282.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 16.1115 (19) ŵ = 0.09 mm−1
b = 7.7040 (9) ÅT = 293 K
c = 23.873 (3) Å0.35 × 0.20 × 0.12 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer		2786 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		1563 reflections with I > 2σ(I)
Tmin = 0.303, Tmax = 0.999Rint = 0.070
13132 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 0.97Δρmax = 0.19 e Å−3
2786 reflectionsΔρmin = −0.18 e Å−3
194 parameters
Special details top

Experimental. A mixture of 3,5-dimethyl-phenol (0,245 g, 2,00 mmol) and 4-methoxycinnamic acid (0.356 g, 2 mmol) was placed in a cylindrical quartz reactor (4 cm diameter). The reactor was then introduced into a CEM Discover microwave reactor [2.45 GHz, adjusted power of 250 W, and an IR temperature detector]. The stirred liquid mixture was irradiated for 5 min at 333 K. The mixture was then allowed to cool and a white solid formed rapidly (< 5 min) at 298 K. This crude solid was filtered off (under nitrogen), washed with anhydrous ethanol (3 × 5 ml), and vacuum dried for 1 h. The solid was further dried under high vacuum (10–2 Torr) at 298 K for 8 h. Recrystallization from dry ethanol gave the title compound as colourless needle-like crystals (yield 65%; m.p. = 413–418 K). 1H NMR (CDCl3, 400 MHz) δ 2.14 (s, 3H); 2.34 (s, 3H); 2.97 (dd, 1H, J = 15.6 and 2.58 Hz); 3.00 (dd, 1H, J = 15.6 and 6.0 Hz); 4.32 (dd, 1H, J = 6.0 and 2.58 Hz); 6.79–6.76 (m, 2H); 6.81–6.80 (m, 2H); 6.96–6.94 (m, 2H). 13C NMR (101 MHz,CDCl3) δ p.p.m. 18.62; 21.08; 37.21; 37.98; 55.25; 114.45; 115.42; 120.47; 127.28; 128.02; 132.32; 136.54; 138.68; 152.03; 158.80; 167.66.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.24519 (9)0.54914 (19)0.37344 (6)0.0544 (5)
O2−0.05956 (11)1.14738 (19)0.42345 (7)0.0669 (6)
O30.25110 (11)0.5854 (2)0.46470 (7)0.0708 (6)
C10.21280 (17)0.5261 (3)0.42587 (11)0.0522 (6)
C20.13392 (15)0.4270 (3)0.42946 (9)0.0536 (7)
H2A0.10800.44970.46540.064*
H2B0.14610.30390.42750.064*
C30.07319 (14)0.4745 (3)0.38271 (8)0.0440 (6)
H30.02780.38990.38340.053*
C40.11783 (14)0.4546 (2)0.32795 (8)0.0412 (5)
C50.07948 (14)0.4014 (3)0.27818 (10)0.0476 (6)
C60.12741 (15)0.3855 (3)0.23005 (10)0.0550 (7)
H60.10180.34880.19720.066*
C70.21175 (16)0.4217 (3)0.22875 (10)0.0542 (6)
C80.24902 (14)0.4748 (3)0.27819 (10)0.0516 (6)
H80.30540.50070.27890.062*
C90.20234 (15)0.4889 (3)0.32602 (9)0.0449 (6)
C10−0.01234 (15)0.3653 (4)0.27682 (11)0.0681 (7)
H10A−0.02750.32240.24050.102*
H10B−0.04230.47050.28440.102*
H10C−0.02580.28000.30470.102*
C110.26174 (16)0.4012 (4)0.17614 (11)0.0772 (9)
H11A0.29890.30450.18010.116*
H11B0.29320.50500.16950.116*
H11C0.22510.38080.14510.116*
C120.03573 (14)0.6540 (3)0.39205 (8)0.0408 (6)
C13−0.03718 (15)0.6726 (3)0.42207 (9)0.0530 (7)
H13−0.06440.57350.43470.064*
C14−0.07116 (16)0.8339 (3)0.43401 (9)0.0548 (7)
H14−0.12030.84210.45430.066*
C15−0.03148 (15)0.9819 (3)0.41561 (9)0.0484 (6)
C160.04172 (15)0.9657 (3)0.38571 (9)0.0514 (6)
H160.06911.06480.37330.062*
C170.07453 (14)0.8045 (3)0.37405 (9)0.0468 (6)
H170.12360.79660.35370.056*
C18−0.13033 (18)1.1710 (3)0.45774 (12)0.0735 (8)
H18A−0.17601.10630.44260.110*
H18B−0.14451.29200.45890.110*
H18C−0.11851.13080.49500.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0486 (10)0.0639 (11)0.0507 (10)−0.0048 (8)−0.0065 (8)−0.0001 (8)
O20.0769 (13)0.0432 (9)0.0805 (12)0.0072 (9)0.0317 (10)0.0016 (8)
O30.0775 (13)0.0771 (13)0.0577 (11)0.0022 (10)−0.0186 (10)−0.0092 (9)
C10.0570 (16)0.0476 (14)0.0519 (16)0.0095 (12)−0.0073 (13)0.0013 (11)
C20.0670 (17)0.0464 (13)0.0476 (14)0.0017 (13)0.0008 (13)0.0073 (10)
C30.0450 (14)0.0394 (12)0.0476 (14)−0.0039 (10)0.0030 (11)0.0050 (10)
C40.0429 (14)0.0358 (11)0.0448 (13)0.0014 (10)−0.0008 (11)0.0016 (9)
C50.0455 (15)0.0470 (13)0.0505 (14)0.0020 (11)−0.0035 (12)−0.0012 (10)
C60.0592 (18)0.0603 (15)0.0454 (14)0.0060 (13)−0.0070 (13)−0.0041 (11)
C70.0554 (17)0.0577 (15)0.0495 (15)0.0090 (12)0.0044 (13)0.0044 (11)
C80.0407 (14)0.0593 (15)0.0547 (15)0.0043 (12)0.0011 (12)0.0069 (12)
C90.0444 (15)0.0450 (13)0.0453 (14)−0.0003 (11)−0.0071 (12)0.0029 (10)
C100.0512 (17)0.0841 (18)0.0691 (17)−0.0054 (15)−0.0056 (14)−0.0105 (15)
C110.072 (2)0.101 (2)0.0585 (18)0.0071 (17)0.0115 (15)−0.0025 (15)
C120.0443 (14)0.0381 (12)0.0398 (12)−0.0016 (10)0.0020 (11)0.0037 (9)
C130.0587 (16)0.0439 (14)0.0563 (15)−0.0034 (12)0.0165 (13)0.0079 (10)
C140.0580 (16)0.0522 (14)0.0543 (15)0.0013 (12)0.0193 (12)0.0060 (11)
C150.0581 (16)0.0409 (13)0.0463 (14)0.0010 (11)0.0087 (12)0.0013 (10)
C160.0543 (16)0.0401 (13)0.0597 (15)−0.0057 (11)0.0104 (13)0.0060 (11)
C170.0400 (13)0.0461 (13)0.0543 (14)−0.0024 (11)0.0078 (11)0.0030 (10)
C180.083 (2)0.0583 (16)0.0797 (19)0.0108 (15)0.0294 (17)−0.0049 (13)
Geometric parameters (Å, º) top
O1—C11.368 (3)C8—H80.9300
O1—C91.405 (2)C10—H10A0.9600
O2—C151.366 (2)C10—H10B0.9600
O2—C181.415 (3)C10—H10C0.9600
O3—C11.203 (3)C11—H11A0.9600
C1—C21.485 (3)C11—H11B0.9600
C2—C31.529 (3)C11—H11C0.9600
C2—H2A0.9700C12—C131.383 (3)
C2—H2B0.9700C12—C171.386 (3)
C3—C41.500 (3)C13—C141.387 (3)
C3—C121.525 (3)C13—H130.9300
C3—H30.9800C14—C151.379 (3)
C4—C91.388 (3)C14—H140.9300
C4—C51.400 (3)C15—C161.384 (3)
C5—C61.390 (3)C16—C171.378 (3)
C5—C101.506 (3)C16—H160.9300
C6—C71.388 (3)C17—H170.9300
C6—H60.9300C18—H18A0.9600
C7—C81.386 (3)C18—H18B0.9600
C7—C111.500 (3)C18—H18C0.9600
C8—C91.372 (3)
C1—O1—C9120.47 (19)C5—C10—H10B109.5
C15—O2—C18117.79 (18)H10A—C10—H10B109.5
O3—C1—O1117.4 (2)C5—C10—H10C109.5
O3—C1—C2126.1 (2)H10A—C10—H10C109.5
O1—C1—C2116.5 (2)H10B—C10—H10C109.5
C1—C2—C3112.50 (18)C7—C11—H11A109.5
C1—C2—H2A109.1C7—C11—H11B109.5
C3—C2—H2A109.1H11A—C11—H11B109.5
C1—C2—H2B109.1C7—C11—H11C109.5
C3—C2—H2B109.1H11A—C11—H11C109.5
H2A—C2—H2B107.8H11B—C11—H11C109.5
C4—C3—C12114.20 (16)C13—C12—C17117.19 (19)
C4—C3—C2107.76 (19)C13—C12—C3120.38 (18)
C12—C3—C2111.32 (17)C17—C12—C3122.3 (2)
C4—C3—H3107.8C12—C13—C14122.3 (2)
C12—C3—H3107.8C12—C13—H13118.9
C2—C3—H3107.8C14—C13—H13118.9
C9—C4—C5117.4 (2)C15—C14—C13119.5 (2)
C9—C4—C3118.67 (19)C15—C14—H14120.3
C5—C4—C3123.9 (2)C13—C14—H14120.3
C6—C5—C4118.8 (2)O2—C15—C14125.1 (2)
C6—C5—C10120.8 (2)O2—C15—C16115.91 (19)
C4—C5—C10120.4 (2)C14—C15—C16119.0 (2)
C7—C6—C5123.0 (2)C17—C16—C15120.8 (2)
C7—C6—H6118.5C17—C16—H16119.6
C5—C6—H6118.5C15—C16—H16119.6
C8—C7—C6117.7 (2)C16—C17—C12121.2 (2)
C8—C7—C11120.8 (2)C16—C17—H17119.4
C6—C7—C11121.5 (2)C12—C17—H17119.4
C9—C8—C7119.7 (2)O2—C18—H18A109.5
C9—C8—H8120.2O2—C18—H18B109.5
C7—C8—H8120.2H18A—C18—H18B109.5
C8—C9—C4123.4 (2)O2—C18—H18C109.5
C8—C9—O1115.3 (2)H18A—C18—H18C109.5
C4—C9—O1121.2 (2)H18B—C18—H18C109.5
C5—C10—H10A109.5
C9—O1—C1—O3−177.71 (19)C5—C4—C9—C80.6 (3)
C9—O1—C1—C23.3 (3)C3—C4—C9—C8−179.98 (19)
O3—C1—C2—C3140.3 (2)C5—C4—C9—O1177.58 (18)
O1—C1—C2—C3−40.8 (3)C3—C4—C9—O1−3.0 (3)
C1—C2—C3—C453.4 (2)C1—O1—C9—C8−162.75 (19)
C1—C2—C3—C12−72.6 (2)C1—O1—C9—C420.1 (3)
C12—C3—C4—C991.7 (2)C4—C3—C12—C13147.3 (2)
C2—C3—C4—C9−32.5 (2)C2—C3—C12—C13−90.4 (3)
C12—C3—C4—C5−88.9 (3)C4—C3—C12—C17−36.4 (3)
C2—C3—C4—C5146.8 (2)C2—C3—C12—C1785.9 (2)
C9—C4—C5—C60.2 (3)C17—C12—C13—C140.1 (4)
C3—C4—C5—C6−179.20 (19)C3—C12—C13—C14176.6 (2)
C9—C4—C5—C10−178.8 (2)C12—C13—C14—C15−0.1 (4)
C3—C4—C5—C101.8 (3)C18—O2—C15—C146.6 (3)
C4—C5—C6—C7−0.7 (3)C18—O2—C15—C16−174.8 (2)
C10—C5—C6—C7178.2 (2)C13—C14—C15—O2178.3 (2)
C5—C6—C7—C80.5 (3)C13—C14—C15—C16−0.2 (4)
C5—C6—C7—C11179.3 (2)O2—C15—C16—C17−178.3 (2)
C6—C7—C8—C90.3 (3)C14—C15—C16—C170.4 (4)
C11—C7—C8—C9−178.6 (2)C15—C16—C17—C12−0.3 (4)
C7—C8—C9—C4−0.9 (3)C13—C12—C17—C160.1 (3)
C7—C8—C9—O1−177.98 (19)C3—C12—C17—C16−176.36 (19)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C12–C17 benzene ring.
D—H···AD—HH···AD···AD—H···A
C2—H2B···O3i0.972.523.327 (3)140
C3—H3···O2ii0.982.533.446 (3)156
C6—H6···Cg3iii0.932.953.853 (3)165
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C12–C17 benzene ring.
D—H···AD—HH···AD···AD—H···A
C2—H2B···O3i0.972.523.327 (3)140
C3—H3···O2ii0.982.533.446 (3)156
C6—H6···Cg3iii0.932.953.853 (3)165
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC18H18O3
Mr282.32
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)16.1115 (19), 7.7040 (9), 23.873 (3)
V (Å3)2963.2 (6)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.35 × 0.20 × 0.12
Data collection
DiffractometerBruker APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.303, 0.999
No. of measured, independent and
observed [I > 2σ(I)] reflections		13132, 2786, 1563
Rint0.070
(sin θ/λ)max (Å−1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.155, 0.97
No. of reflections2786
No. of parameters194
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.18

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), SHELXL2014 (Sheldrick 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

 

Acknowledgements

The authors thank the Brazilian Federal Agency (CNPq/Brazil) and Fundação de Tecnologia e Ciências (FTC/Portugal) for support of this work.

References

First citationAsai, F., Iinuma, M., Tanaka, T. & Mizuno, M. (1991). Phytochemistry, 30, 3091–3093.  CrossRef CAS Google Scholar
 First citationBruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationJagdale, A. R. & Sudalai, A. (2007). Tetrahedron Lett. 48, 4895–4898.  CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals 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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160430
doi:10.1107/S2414314616004302
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