organic compounds
4-(4-Methoxyphenyl)-5,7-dimethylchroman-2-one
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
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
Structure description
Coumarin derivatives exist widely in nature, especially in plants (Asai et al., 1991), 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 and other complex Dihydrocoumarins may be obtained by methods based on acid-mediated hydroarylation of (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 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.
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 . 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.
details are summarized in Table 2Structural data
CCDC reference: 1465266
10.1107/S2414314616004302/su4021sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004302/su4021Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004302/su4021Isup3.cml
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.
Crystal data, data collection and structure
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.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
and other complex Dihydrocoumarins may be obtained by methods based on acid-mediated hydroarylation of (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 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.
Data collection: SMART (Bruker, 2003); cell
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).Fig. 1. A view of the molecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids. | |
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. |
C18H18O3 | Dx = 1.266 Mg m−3 |
Mr = 282.32 | Melting point: 418 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 16.1115 (19) Å | Cell parameters from 1347 reflections |
b = 7.7040 (9) Å | θ = 3.1–20.8° |
c = 23.873 (3) Å | µ = 0.09 mm−1 |
V = 2963.2 (6) Å3 | T = 293 K |
Z = 8 | Block, colorless |
F(000) = 1200 | 0.35 × 0.20 × 0.12 mm |
Bruker APEX CCD area-detector diffractometer | 2786 independent reflections |
Radiation source: fine-focus sealed tube | 1563 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
φ and ω scans | θmax = 25.7°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −17→19 |
Tmin = 0.303, Tmax = 0.999 | k = −9→9 |
13132 measured reflections | l = −15→29 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-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 reflections | Δρmax = 0.19 e Å−3 |
194 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0059 (10) |
C18H18O3 | V = 2963.2 (6) Å3 |
Mr = 282.32 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 16.1115 (19) Å | µ = 0.09 mm−1 |
b = 7.7040 (9) Å | T = 293 K |
c = 23.873 (3) Å | 0.35 × 0.20 × 0.12 mm |
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 = 0.999 | Rint = 0.070 |
13132 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.19 e Å−3 |
2786 reflections | Δρmin = −0.18 e Å−3 |
194 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.24519 (9) | 0.54914 (19) | 0.37344 (6) | 0.0544 (5) | |
O2 | −0.05956 (11) | 1.14738 (19) | 0.42345 (7) | 0.0669 (6) | |
O3 | 0.25110 (11) | 0.5854 (2) | 0.46470 (7) | 0.0708 (6) | |
C1 | 0.21280 (17) | 0.5261 (3) | 0.42587 (11) | 0.0522 (6) | |
C2 | 0.13392 (15) | 0.4270 (3) | 0.42946 (9) | 0.0536 (7) | |
H2A | 0.1080 | 0.4497 | 0.4654 | 0.064* | |
H2B | 0.1461 | 0.3039 | 0.4275 | 0.064* | |
C3 | 0.07319 (14) | 0.4745 (3) | 0.38271 (8) | 0.0440 (6) | |
H3 | 0.0278 | 0.3899 | 0.3834 | 0.053* | |
C4 | 0.11783 (14) | 0.4546 (2) | 0.32795 (8) | 0.0412 (5) | |
C5 | 0.07948 (14) | 0.4014 (3) | 0.27818 (10) | 0.0476 (6) | |
C6 | 0.12741 (15) | 0.3855 (3) | 0.23005 (10) | 0.0550 (7) | |
H6 | 0.1018 | 0.3488 | 0.1972 | 0.066* | |
C7 | 0.21175 (16) | 0.4217 (3) | 0.22875 (10) | 0.0542 (6) | |
C8 | 0.24902 (14) | 0.4748 (3) | 0.27819 (10) | 0.0516 (6) | |
H8 | 0.3054 | 0.5007 | 0.2789 | 0.062* | |
C9 | 0.20234 (15) | 0.4889 (3) | 0.32602 (9) | 0.0449 (6) | |
C10 | −0.01234 (15) | 0.3653 (4) | 0.27682 (11) | 0.0681 (7) | |
H10A | −0.0275 | 0.3224 | 0.2405 | 0.102* | |
H10B | −0.0423 | 0.4705 | 0.2844 | 0.102* | |
H10C | −0.0258 | 0.2800 | 0.3047 | 0.102* | |
C11 | 0.26174 (16) | 0.4012 (4) | 0.17614 (11) | 0.0772 (9) | |
H11A | 0.2989 | 0.3045 | 0.1801 | 0.116* | |
H11B | 0.2932 | 0.5050 | 0.1695 | 0.116* | |
H11C | 0.2251 | 0.3808 | 0.1451 | 0.116* | |
C12 | 0.03573 (14) | 0.6540 (3) | 0.39205 (8) | 0.0408 (6) | |
C13 | −0.03718 (15) | 0.6726 (3) | 0.42207 (9) | 0.0530 (7) | |
H13 | −0.0644 | 0.5735 | 0.4347 | 0.064* | |
C14 | −0.07116 (16) | 0.8339 (3) | 0.43401 (9) | 0.0548 (7) | |
H14 | −0.1203 | 0.8421 | 0.4543 | 0.066* | |
C15 | −0.03148 (15) | 0.9819 (3) | 0.41561 (9) | 0.0484 (6) | |
C16 | 0.04172 (15) | 0.9657 (3) | 0.38571 (9) | 0.0514 (6) | |
H16 | 0.0691 | 1.0648 | 0.3733 | 0.062* | |
C17 | 0.07453 (14) | 0.8045 (3) | 0.37405 (9) | 0.0468 (6) | |
H17 | 0.1236 | 0.7966 | 0.3537 | 0.056* | |
C18 | −0.13033 (18) | 1.1710 (3) | 0.45774 (12) | 0.0735 (8) | |
H18A | −0.1760 | 1.1063 | 0.4426 | 0.110* | |
H18B | −0.1445 | 1.2920 | 0.4589 | 0.110* | |
H18C | −0.1185 | 1.1308 | 0.4950 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0486 (10) | 0.0639 (11) | 0.0507 (10) | −0.0048 (8) | −0.0065 (8) | −0.0001 (8) |
O2 | 0.0769 (13) | 0.0432 (9) | 0.0805 (12) | 0.0072 (9) | 0.0317 (10) | 0.0016 (8) |
O3 | 0.0775 (13) | 0.0771 (13) | 0.0577 (11) | 0.0022 (10) | −0.0186 (10) | −0.0092 (9) |
C1 | 0.0570 (16) | 0.0476 (14) | 0.0519 (16) | 0.0095 (12) | −0.0073 (13) | 0.0013 (11) |
C2 | 0.0670 (17) | 0.0464 (13) | 0.0476 (14) | 0.0017 (13) | 0.0008 (13) | 0.0073 (10) |
C3 | 0.0450 (14) | 0.0394 (12) | 0.0476 (14) | −0.0039 (10) | 0.0030 (11) | 0.0050 (10) |
C4 | 0.0429 (14) | 0.0358 (11) | 0.0448 (13) | 0.0014 (10) | −0.0008 (11) | 0.0016 (9) |
C5 | 0.0455 (15) | 0.0470 (13) | 0.0505 (14) | 0.0020 (11) | −0.0035 (12) | −0.0012 (10) |
C6 | 0.0592 (18) | 0.0603 (15) | 0.0454 (14) | 0.0060 (13) | −0.0070 (13) | −0.0041 (11) |
C7 | 0.0554 (17) | 0.0577 (15) | 0.0495 (15) | 0.0090 (12) | 0.0044 (13) | 0.0044 (11) |
C8 | 0.0407 (14) | 0.0593 (15) | 0.0547 (15) | 0.0043 (12) | 0.0011 (12) | 0.0069 (12) |
C9 | 0.0444 (15) | 0.0450 (13) | 0.0453 (14) | −0.0003 (11) | −0.0071 (12) | 0.0029 (10) |
C10 | 0.0512 (17) | 0.0841 (18) | 0.0691 (17) | −0.0054 (15) | −0.0056 (14) | −0.0105 (15) |
C11 | 0.072 (2) | 0.101 (2) | 0.0585 (18) | 0.0071 (17) | 0.0115 (15) | −0.0025 (15) |
C12 | 0.0443 (14) | 0.0381 (12) | 0.0398 (12) | −0.0016 (10) | 0.0020 (11) | 0.0037 (9) |
C13 | 0.0587 (16) | 0.0439 (14) | 0.0563 (15) | −0.0034 (12) | 0.0165 (13) | 0.0079 (10) |
C14 | 0.0580 (16) | 0.0522 (14) | 0.0543 (15) | 0.0013 (12) | 0.0193 (12) | 0.0060 (11) |
C15 | 0.0581 (16) | 0.0409 (13) | 0.0463 (14) | 0.0010 (11) | 0.0087 (12) | 0.0013 (10) |
C16 | 0.0543 (16) | 0.0401 (13) | 0.0597 (15) | −0.0057 (11) | 0.0104 (13) | 0.0060 (11) |
C17 | 0.0400 (13) | 0.0461 (13) | 0.0543 (14) | −0.0024 (11) | 0.0078 (11) | 0.0030 (10) |
C18 | 0.083 (2) | 0.0583 (16) | 0.0797 (19) | 0.0108 (15) | 0.0294 (17) | −0.0049 (13) |
O1—C1 | 1.368 (3) | C8—H8 | 0.9300 |
O1—C9 | 1.405 (2) | C10—H10A | 0.9600 |
O2—C15 | 1.366 (2) | C10—H10B | 0.9600 |
O2—C18 | 1.415 (3) | C10—H10C | 0.9600 |
O3—C1 | 1.203 (3) | C11—H11A | 0.9600 |
C1—C2 | 1.485 (3) | C11—H11B | 0.9600 |
C2—C3 | 1.529 (3) | C11—H11C | 0.9600 |
C2—H2A | 0.9700 | C12—C13 | 1.383 (3) |
C2—H2B | 0.9700 | C12—C17 | 1.386 (3) |
C3—C4 | 1.500 (3) | C13—C14 | 1.387 (3) |
C3—C12 | 1.525 (3) | C13—H13 | 0.9300 |
C3—H3 | 0.9800 | C14—C15 | 1.379 (3) |
C4—C9 | 1.388 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.400 (3) | C15—C16 | 1.384 (3) |
C5—C6 | 1.390 (3) | C16—C17 | 1.378 (3) |
C5—C10 | 1.506 (3) | C16—H16 | 0.9300 |
C6—C7 | 1.388 (3) | C17—H17 | 0.9300 |
C6—H6 | 0.9300 | C18—H18A | 0.9600 |
C7—C8 | 1.386 (3) | C18—H18B | 0.9600 |
C7—C11 | 1.500 (3) | C18—H18C | 0.9600 |
C8—C9 | 1.372 (3) | ||
C1—O1—C9 | 120.47 (19) | C5—C10—H10B | 109.5 |
C15—O2—C18 | 117.79 (18) | H10A—C10—H10B | 109.5 |
O3—C1—O1 | 117.4 (2) | C5—C10—H10C | 109.5 |
O3—C1—C2 | 126.1 (2) | H10A—C10—H10C | 109.5 |
O1—C1—C2 | 116.5 (2) | H10B—C10—H10C | 109.5 |
C1—C2—C3 | 112.50 (18) | C7—C11—H11A | 109.5 |
C1—C2—H2A | 109.1 | C7—C11—H11B | 109.5 |
C3—C2—H2A | 109.1 | H11A—C11—H11B | 109.5 |
C1—C2—H2B | 109.1 | C7—C11—H11C | 109.5 |
C3—C2—H2B | 109.1 | H11A—C11—H11C | 109.5 |
H2A—C2—H2B | 107.8 | H11B—C11—H11C | 109.5 |
C4—C3—C12 | 114.20 (16) | C13—C12—C17 | 117.19 (19) |
C4—C3—C2 | 107.76 (19) | C13—C12—C3 | 120.38 (18) |
C12—C3—C2 | 111.32 (17) | C17—C12—C3 | 122.3 (2) |
C4—C3—H3 | 107.8 | C12—C13—C14 | 122.3 (2) |
C12—C3—H3 | 107.8 | C12—C13—H13 | 118.9 |
C2—C3—H3 | 107.8 | C14—C13—H13 | 118.9 |
C9—C4—C5 | 117.4 (2) | C15—C14—C13 | 119.5 (2) |
C9—C4—C3 | 118.67 (19) | C15—C14—H14 | 120.3 |
C5—C4—C3 | 123.9 (2) | C13—C14—H14 | 120.3 |
C6—C5—C4 | 118.8 (2) | O2—C15—C14 | 125.1 (2) |
C6—C5—C10 | 120.8 (2) | O2—C15—C16 | 115.91 (19) |
C4—C5—C10 | 120.4 (2) | C14—C15—C16 | 119.0 (2) |
C7—C6—C5 | 123.0 (2) | C17—C16—C15 | 120.8 (2) |
C7—C6—H6 | 118.5 | C17—C16—H16 | 119.6 |
C5—C6—H6 | 118.5 | C15—C16—H16 | 119.6 |
C8—C7—C6 | 117.7 (2) | C16—C17—C12 | 121.2 (2) |
C8—C7—C11 | 120.8 (2) | C16—C17—H17 | 119.4 |
C6—C7—C11 | 121.5 (2) | C12—C17—H17 | 119.4 |
C9—C8—C7 | 119.7 (2) | O2—C18—H18A | 109.5 |
C9—C8—H8 | 120.2 | O2—C18—H18B | 109.5 |
C7—C8—H8 | 120.2 | H18A—C18—H18B | 109.5 |
C8—C9—C4 | 123.4 (2) | O2—C18—H18C | 109.5 |
C8—C9—O1 | 115.3 (2) | H18A—C18—H18C | 109.5 |
C4—C9—O1 | 121.2 (2) | H18B—C18—H18C | 109.5 |
C5—C10—H10A | 109.5 | ||
C9—O1—C1—O3 | −177.71 (19) | C5—C4—C9—C8 | 0.6 (3) |
C9—O1—C1—C2 | 3.3 (3) | C3—C4—C9—C8 | −179.98 (19) |
O3—C1—C2—C3 | 140.3 (2) | C5—C4—C9—O1 | 177.58 (18) |
O1—C1—C2—C3 | −40.8 (3) | C3—C4—C9—O1 | −3.0 (3) |
C1—C2—C3—C4 | 53.4 (2) | C1—O1—C9—C8 | −162.75 (19) |
C1—C2—C3—C12 | −72.6 (2) | C1—O1—C9—C4 | 20.1 (3) |
C12—C3—C4—C9 | 91.7 (2) | C4—C3—C12—C13 | 147.3 (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—C5 | 146.8 (2) | C2—C3—C12—C17 | 85.9 (2) |
C9—C4—C5—C6 | 0.2 (3) | C17—C12—C13—C14 | 0.1 (4) |
C3—C4—C5—C6 | −179.20 (19) | C3—C12—C13—C14 | 176.6 (2) |
C9—C4—C5—C10 | −178.8 (2) | C12—C13—C14—C15 | −0.1 (4) |
C3—C4—C5—C10 | 1.8 (3) | C18—O2—C15—C14 | 6.6 (3) |
C4—C5—C6—C7 | −0.7 (3) | C18—O2—C15—C16 | −174.8 (2) |
C10—C5—C6—C7 | 178.2 (2) | C13—C14—C15—O2 | 178.3 (2) |
C5—C6—C7—C8 | 0.5 (3) | C13—C14—C15—C16 | −0.2 (4) |
C5—C6—C7—C11 | 179.3 (2) | O2—C15—C16—C17 | −178.3 (2) |
C6—C7—C8—C9 | 0.3 (3) | C14—C15—C16—C17 | 0.4 (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—C16 | 0.1 (3) |
C7—C8—C9—O1 | −177.98 (19) | C3—C12—C17—C16 | −176.36 (19) |
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+1/2, y−1/2, z; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2. |
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+1/2, y−1/2, z; (ii) x, y−1, z; (iii) −x, y−1/2, −z+1/2. |
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) |
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), 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
Asai, F., Iinuma, M., Tanaka, T. & Mizuno, M. (1991). Phytochemistry, 30, 3091–3093. CrossRef CAS Google Scholar
Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jagdale, A. R. & Sudalai, A. (2007). Tetrahedron Lett. 48, 4895–4898. CrossRef CAS Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, 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.