In the title compound, C
25H
20O
4, the dihydropyran rings adopt distorted sofa conformations. The molecule comprises two planar regions which form a dihedral angle of 62.56 (3)°. C—H
π interactions link the molecules to form centrosymmetric dimeric pairs. The dimers are interlinked along the [101] direction by C—H
O hydrogen bonds.
Supporting information
CCDC reference: 214620
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.153
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
To a refluxing solution of 4-hydroxy-α-naphthocoumarin (1 mmol) in 10 ml of dry ethanol, 2-(3-methyl-2-butenyloxy)benzaldehyde (1 mmol) was added and the reaction mixture was refluxed for 7 h; evaporation of the solvent and flash column chromatography (hexane/ethyl acetate) afforded the title compound as a colourless solid with 22% yield. Single crystals were grown by slow evaporation from a solution in methanol–chloroform (1:1).
The H atoms were positioned geometrically and were treated as riding on their parent C atoms; refined isotropically with phenyl C—H distance of 0.93 Å, methyl C—H distance of 0.96 Å, methylene C—H distance of 0.98 Å and ethylene C—H distance of 0.97 Å.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
[6a,16
b]-
cis-7,7-Dimethyl-6,6a,7,16
b- tetrahydrochromeno[4',3':3,4]pyrano[3,2-
c]-
α-naphthocoumarin
top
Crystal data top
C25H20O4 | F(000) = 808 |
Mr = 384.41 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 12.172 (1) Å | θ = 15–35° |
b = 9.140 (1) Å | µ = 0.72 mm−1 |
c = 18.081 (1) Å | T = 293 K |
β = 106.58 (1)° | Block, colourless |
V = 1927.9 (3) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.014 |
Radiation source: fine-focus sealed tube | θmax = 71.9°, θmin = 3.9° |
Graphite monochromator | h = 0→15 |
ω–2θ scans | k = 0→11 |
3967 measured reflections | l = −22→21 |
3783 independent reflections | 3 standard reflections every 100 reflections |
2686 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0905P)2 + 0.3018P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3783 reflections | Δρmax = 0.20 e Å−3 |
263 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0045 (5) |
Crystal data top
C25H20O4 | V = 1927.9 (3) Å3 |
Mr = 384.41 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 12.172 (1) Å | µ = 0.72 mm−1 |
b = 9.140 (1) Å | T = 293 K |
c = 18.081 (1) Å | 0.30 × 0.25 × 0.20 mm |
β = 106.58 (1)° | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.014 |
3967 measured reflections | 3 standard reflections every 100 reflections |
3783 independent reflections | intensity decay: none |
2686 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.20 e Å−3 |
3783 reflections | Δρmin = −0.25 e Å−3 |
263 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.68391 (10) | 0.79519 (16) | 0.10818 (7) | 0.0528 (4) | |
C2 | 0.68450 (16) | 0.7257 (2) | 0.17611 (10) | 0.0508 (5) | |
C3 | 0.58192 (15) | 0.6570 (2) | 0.18167 (9) | 0.0440 (4) | |
C4 | 0.48988 (14) | 0.6497 (2) | 0.11790 (9) | 0.0417 (4) | |
C5 | 0.49193 (14) | 0.7184 (2) | 0.04648 (9) | 0.0430 (4) | |
C6 | 0.39750 (16) | 0.7161 (2) | −0.02126 (10) | 0.0516 (5) | |
H6 | 0.3305 | 0.6674 | −0.0211 | 0.062* | |
C7 | 0.40477 (16) | 0.7847 (2) | −0.08620 (10) | 0.0531 (5) | |
H7 | 0.3425 | 0.7820 | −0.1302 | 0.064* | |
C8 | 0.50480 (15) | 0.8601 (2) | −0.08835 (9) | 0.0452 (4) | |
C9 | 0.51411 (18) | 0.9306 (2) | −0.15618 (11) | 0.0527 (5) | |
H9 | 0.4522 | 0.9295 | −0.2004 | 0.063* | |
C10 | 0.6122 (2) | 0.9996 (2) | −0.15725 (12) | 0.0583 (5) | |
H10 | 0.6172 | 1.0435 | −0.2026 | 0.070* | |
C11 | 0.70632 (19) | 1.0058 (2) | −0.09097 (12) | 0.0597 (5) | |
H11 | 0.7725 | 1.0552 | −0.0923 | 0.072* | |
C12 | 0.70080 (17) | 0.9394 (2) | −0.02445 (11) | 0.0530 (5) | |
H12 | 0.7635 | 0.9433 | 0.0193 | 0.064* | |
C13 | 0.60074 (15) | 0.8649 (2) | −0.02168 (9) | 0.0436 (4) | |
C14 | 0.58970 (15) | 0.7905 (2) | 0.04481 (9) | 0.0430 (4) | |
O15 | 0.39235 (10) | 0.57902 (16) | 0.11412 (7) | 0.0517 (4) | |
C16 | 0.37477 (15) | 0.5139 (2) | 0.18455 (11) | 0.0456 (4) | |
C17 | 0.49121 (16) | 0.4570 (2) | 0.23484 (11) | 0.0470 (4) | |
H17 | 0.5171 | 0.3844 | 0.2036 | 0.056* | |
C18 | 0.4903 (2) | 0.3799 (2) | 0.30928 (13) | 0.0616 (6) | |
H18A | 0.4292 | 0.3079 | 0.2975 | 0.074* | |
H18B | 0.5622 | 0.3277 | 0.3289 | 0.074* | |
O19 | 0.47520 (15) | 0.4735 (2) | 0.36842 (9) | 0.0742 (5) | |
C20 | 0.52330 (19) | 0.6102 (3) | 0.37570 (11) | 0.0598 (6) | |
C21 | 0.5152 (2) | 0.6896 (4) | 0.43913 (13) | 0.0804 (8) | |
H21 | 0.4833 | 0.6471 | 0.4750 | 0.096* | |
C22 | 0.5541 (2) | 0.8309 (4) | 0.44906 (15) | 0.0878 (9) | |
H22 | 0.5500 | 0.8834 | 0.4922 | 0.105* | |
C23 | 0.5995 (2) | 0.8958 (3) | 0.39522 (16) | 0.0802 (8) | |
H23 | 0.6236 | 0.9927 | 0.4010 | 0.096* | |
C24 | 0.60862 (19) | 0.8146 (3) | 0.33238 (12) | 0.0613 (6) | |
H24 | 0.6399 | 0.8581 | 0.2965 | 0.074* | |
C25 | 0.57236 (16) | 0.6705 (2) | 0.32170 (10) | 0.0509 (5) | |
C26 | 0.58379 (15) | 0.5763 (2) | 0.25478 (10) | 0.0448 (4) | |
H26 | 0.6580 | 0.5264 | 0.2722 | 0.054* | |
C27 | 0.31806 (17) | 0.6303 (2) | 0.21983 (12) | 0.0566 (5) | |
H27A | 0.3717 | 0.7076 | 0.2397 | 0.085* | |
H27B | 0.2932 | 0.5886 | 0.2611 | 0.085* | |
H27C | 0.2531 | 0.6688 | 0.1812 | 0.085* | |
C28 | 0.2908 (2) | 0.3907 (3) | 0.15310 (14) | 0.0659 (6) | |
H28A | 0.3277 | 0.3169 | 0.1308 | 0.099* | |
H28B | 0.2257 | 0.4285 | 0.1144 | 0.099* | |
H28C | 0.2660 | 0.3486 | 0.1943 | 0.099* | |
O29 | 0.77551 (12) | 0.7283 (2) | 0.22640 (8) | 0.0734 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0416 (6) | 0.0783 (10) | 0.0355 (6) | −0.0165 (6) | 0.0060 (5) | 0.0084 (6) |
C2 | 0.0420 (9) | 0.0735 (14) | 0.0350 (8) | −0.0080 (9) | 0.0079 (7) | 0.0073 (9) |
C3 | 0.0413 (9) | 0.0565 (11) | 0.0352 (8) | −0.0029 (8) | 0.0126 (7) | 0.0027 (8) |
C4 | 0.0350 (8) | 0.0533 (10) | 0.0391 (8) | −0.0036 (7) | 0.0142 (7) | −0.0002 (8) |
C5 | 0.0375 (9) | 0.0579 (11) | 0.0339 (8) | −0.0039 (8) | 0.0108 (7) | −0.0005 (8) |
C6 | 0.0392 (9) | 0.0742 (14) | 0.0397 (9) | −0.0080 (9) | 0.0087 (7) | −0.0024 (9) |
C7 | 0.0441 (10) | 0.0752 (14) | 0.0366 (9) | 0.0014 (9) | 0.0061 (7) | −0.0008 (9) |
C8 | 0.0518 (10) | 0.0504 (10) | 0.0346 (8) | 0.0050 (8) | 0.0141 (7) | −0.0008 (8) |
C9 | 0.0675 (12) | 0.0525 (11) | 0.0385 (9) | 0.0088 (10) | 0.0157 (8) | 0.0040 (8) |
C10 | 0.0824 (14) | 0.0521 (12) | 0.0466 (10) | 0.0051 (11) | 0.0283 (10) | 0.0088 (9) |
C11 | 0.0701 (13) | 0.0575 (13) | 0.0600 (12) | −0.0119 (11) | 0.0323 (10) | 0.0019 (10) |
C12 | 0.0548 (11) | 0.0606 (12) | 0.0455 (10) | −0.0092 (9) | 0.0173 (8) | 0.0013 (9) |
C13 | 0.0474 (9) | 0.0505 (10) | 0.0355 (8) | −0.0027 (8) | 0.0159 (7) | −0.0020 (8) |
C14 | 0.0379 (8) | 0.0581 (11) | 0.0322 (8) | −0.0032 (8) | 0.0087 (6) | −0.0013 (7) |
O15 | 0.0405 (6) | 0.0710 (9) | 0.0454 (7) | −0.0114 (6) | 0.0150 (5) | 0.0052 (6) |
C16 | 0.0440 (9) | 0.0460 (10) | 0.0536 (10) | −0.0024 (8) | 0.0248 (8) | 0.0046 (8) |
C17 | 0.0494 (10) | 0.0454 (10) | 0.0535 (10) | 0.0080 (8) | 0.0264 (8) | 0.0046 (8) |
C18 | 0.0693 (13) | 0.0545 (12) | 0.0707 (14) | 0.0104 (10) | 0.0353 (11) | 0.0172 (10) |
O19 | 0.0956 (12) | 0.0789 (11) | 0.0657 (9) | 0.0106 (10) | 0.0513 (9) | 0.0170 (8) |
C20 | 0.0644 (13) | 0.0738 (15) | 0.0452 (10) | 0.0197 (11) | 0.0220 (9) | 0.0104 (10) |
C21 | 0.0923 (18) | 0.105 (2) | 0.0498 (12) | 0.0325 (17) | 0.0304 (12) | 0.0051 (13) |
C22 | 0.0889 (18) | 0.112 (2) | 0.0608 (15) | 0.0295 (18) | 0.0194 (13) | −0.0225 (16) |
C23 | 0.0783 (16) | 0.0783 (17) | 0.0729 (16) | 0.0158 (14) | 0.0035 (13) | −0.0183 (13) |
C24 | 0.0589 (12) | 0.0695 (14) | 0.0495 (11) | 0.0082 (11) | 0.0058 (9) | −0.0006 (10) |
C25 | 0.0476 (10) | 0.0636 (12) | 0.0403 (9) | 0.0114 (9) | 0.0109 (7) | 0.0060 (9) |
C26 | 0.0439 (9) | 0.0540 (11) | 0.0391 (9) | 0.0038 (8) | 0.0162 (7) | 0.0069 (8) |
C27 | 0.0539 (11) | 0.0575 (12) | 0.0645 (12) | 0.0108 (9) | 0.0268 (10) | 0.0052 (10) |
C28 | 0.0615 (13) | 0.0586 (13) | 0.0824 (15) | −0.0109 (10) | 0.0279 (11) | −0.0015 (11) |
O29 | 0.0465 (8) | 0.1216 (14) | 0.0433 (7) | −0.0230 (8) | −0.0011 (6) | 0.0180 (8) |
Geometric parameters (Å, º) top
O1—C14 | 1.371 (2) | C16—C28 | 1.518 (3) |
O1—C2 | 1.381 (2) | C16—C17 | 1.540 (3) |
C2—O29 | 1.216 (2) | C17—C18 | 1.522 (3) |
C2—C3 | 1.427 (2) | C17—C26 | 1.535 (3) |
C3—C4 | 1.361 (2) | C17—H17 | 0.98 |
C3—C26 | 1.508 (2) | C18—O19 | 1.422 (3) |
C4—O15 | 1.336 (2) | C18—H18A | 0.97 |
C4—C5 | 1.443 (2) | C18—H18B | 0.97 |
C5—C14 | 1.368 (2) | O19—C20 | 1.370 (3) |
C5—C6 | 1.421 (2) | C20—C21 | 1.385 (3) |
C6—C7 | 1.356 (3) | C20—C25 | 1.395 (3) |
C6—H6 | 0.93 | C21—C22 | 1.370 (4) |
C7—C8 | 1.409 (3) | C21—H21 | 0.93 |
C7—H7 | 0.93 | C22—C23 | 1.382 (4) |
C8—C9 | 1.418 (2) | C22—H22 | 0.93 |
C8—C13 | 1.420 (2) | C23—C24 | 1.388 (3) |
C9—C10 | 1.356 (3) | C23—H23 | 0.93 |
C9—H9 | 0.93 | C24—C25 | 1.385 (3) |
C10—C11 | 1.403 (3) | C24—H24 | 0.93 |
C10—H10 | 0.93 | C25—C26 | 1.523 (3) |
C11—C12 | 1.366 (3) | C26—H26 | 0.98 |
C11—H11 | 0.93 | C27—H27A | 0.96 |
C12—C13 | 1.409 (3) | C27—H27B | 0.96 |
C12—H12 | 0.93 | C27—H27C | 0.96 |
C13—C14 | 1.420 (2) | C28—H28A | 0.96 |
O15—C16 | 1.476 (2) | C28—H28B | 0.96 |
C16—C27 | 1.505 (3) | C28—H28C | 0.96 |
| | | |
C14—O1—C2 | 121.31 (14) | C18—C17—C16 | 116.18 (15) |
O29—C2—O1 | 115.36 (16) | C26—C17—C16 | 112.90 (15) |
O29—C2—C3 | 125.78 (17) | C18—C17—H17 | 106.3 |
O1—C2—C3 | 118.86 (15) | C26—C17—H17 | 106.3 |
C4—C3—C2 | 119.17 (16) | C16—C17—H17 | 106.3 |
C4—C3—C26 | 121.43 (16) | O19—C18—C17 | 114.94 (17) |
C2—C3—C26 | 118.84 (15) | O19—C18—H18A | 108.5 |
O15—C4—C3 | 124.88 (16) | C17—C18—H18A | 108.5 |
O15—C4—C5 | 114.00 (14) | O19—C18—H18B | 108.5 |
C3—C4—C5 | 121.11 (16) | C17—C18—H18B | 108.5 |
C14—C5—C6 | 118.87 (16) | H18A—C18—H18B | 107.5 |
C14—C5—C4 | 117.83 (15) | C20—O19—C18 | 118.51 (15) |
C6—C5—C4 | 123.30 (16) | O19—C20—C21 | 115.4 (2) |
C7—C6—C5 | 120.21 (17) | O19—C20—C25 | 123.34 (19) |
C7—C6—H6 | 119.9 | C21—C20—C25 | 121.2 (2) |
C5—C6—H6 | 119.9 | C22—C21—C20 | 119.9 (3) |
C6—C7—C8 | 121.36 (16) | C22—C21—H21 | 120.0 |
C6—C7—H7 | 119.3 | C20—C21—H21 | 120.0 |
C8—C7—H7 | 119.3 | C21—C22—C23 | 120.3 (2) |
C7—C8—C9 | 121.94 (17) | C21—C22—H22 | 119.8 |
C7—C8—C13 | 119.96 (16) | C23—C22—H22 | 119.8 |
C9—C8—C13 | 118.10 (17) | C22—C23—C24 | 119.2 (3) |
C10—C9—C8 | 120.79 (18) | C22—C23—H23 | 120.4 |
C10—C9—H9 | 119.6 | C24—C23—H23 | 120.4 |
C8—C9—H9 | 119.6 | C25—C24—C23 | 121.7 (2) |
C9—C10—C11 | 120.95 (18) | C25—C24—H24 | 119.1 |
C9—C10—H10 | 119.5 | C23—C24—H24 | 119.1 |
C11—C10—H10 | 119.5 | C24—C25—C20 | 117.5 (2) |
C12—C11—C10 | 120.07 (19) | C24—C25—C26 | 123.40 (18) |
C12—C11—H11 | 120.0 | C20—C25—C26 | 119.14 (19) |
C10—C11—H11 | 120.0 | C3—C26—C25 | 115.97 (16) |
C11—C12—C13 | 120.43 (19) | C3—C26—C17 | 108.37 (14) |
C11—C12—H12 | 119.8 | C25—C26—C17 | 111.14 (14) |
C13—C12—H12 | 119.8 | C3—C26—H26 | 107.0 |
C12—C13—C8 | 119.64 (16) | C25—C26—H26 | 107.0 |
C12—C13—C14 | 123.58 (16) | C17—C26—H26 | 107.0 |
C8—C13—C14 | 116.77 (16) | C16—C27—H27A | 109.5 |
C5—C14—O1 | 121.47 (16) | C16—C27—H27B | 109.5 |
C5—C14—C13 | 122.83 (16) | H27A—C27—H27B | 109.5 |
O1—C14—C13 | 115.70 (15) | C16—C27—H27C | 109.5 |
C4—O15—C16 | 119.77 (13) | H27A—C27—H27C | 109.5 |
O15—C16—C27 | 106.10 (15) | H27B—C27—H27C | 109.5 |
O15—C16—C28 | 102.94 (15) | C16—C28—H28A | 109.5 |
C27—C16—C28 | 110.00 (16) | C16—C28—H28B | 109.5 |
O15—C16—C17 | 108.08 (13) | H28A—C28—H28B | 109.5 |
C27—C16—C17 | 116.39 (16) | C16—C28—H28C | 109.5 |
C28—C16—C17 | 112.25 (17) | H28A—C28—H28C | 109.5 |
C18—C17—C26 | 108.12 (16) | H28B—C28—H28C | 109.5 |
| | | |
C14—O1—C2—O29 | 174.79 (19) | C3—C4—O15—C16 | 6.0 (3) |
C14—O1—C2—C3 | −4.6 (3) | C5—C4—O15—C16 | −175.06 (15) |
O29—C2—C3—C4 | −173.1 (2) | C4—O15—C16—C27 | 90.5 (2) |
O1—C2—C3—C4 | 6.2 (3) | C4—O15—C16—C28 | −153.9 (2) |
O29—C2—C3—C26 | −1.6 (3) | C4—O15—C16—C17 | −35.0 (2) |
O1—C2—C3—C26 | 177.76 (17) | O15—C16—C17—C18 | −177.69 (16) |
C2—C3—C4—O15 | 174.76 (18) | C27—C16—C17—C18 | 63.1 (2) |
C26—C3—C4—O15 | 3.4 (3) | C28—C16—C17—C18 | −64.9 (2) |
C2—C3—C4—C5 | −4.1 (3) | O15—C16—C17—C26 | 56.59 (19) |
C26—C3—C4—C5 | −175.5 (2) | C27—C16—C17—C26 | −62.6 (2) |
O15—C4—C5—C14 | −178.61 (17) | C28—C16—C17—C26 | 169.42 (15) |
C3—C4—C5—C14 | 0.4 (3) | C26—C17—C18—O19 | 55.3 (2) |
O15—C4—C5—C6 | 2.2 (3) | C16—C17—C18—O19 | −72.8 (2) |
C3—C4—C5—C6 | −178.86 (19) | C17—C18—O19—C20 | −35.4 (3) |
C14—C5—C6—C7 | −0.1 (3) | C18—O19—C20—C21 | −173.70 (19) |
C4—C5—C6—C7 | 179.11 (19) | C18—O19—C20—C25 | 9.4 (3) |
C5—C6—C7—C8 | −0.3 (3) | O19—C20—C21—C22 | −175.9 (2) |
C6—C7—C8—C9 | 179.13 (19) | C25—C20—C21—C22 | 1.0 (4) |
C6—C7—C8—C13 | 0.2 (3) | C20—C21—C22—C23 | 1.3 (4) |
C7—C8—C9—C10 | −178.52 (19) | C21—C22—C23—C24 | −2.1 (4) |
C13—C8—C9—C10 | 0.5 (3) | C22—C23—C24—C25 | 0.7 (3) |
C8—C9—C10—C11 | −1.3 (3) | C23—C24—C25—C20 | 1.5 (3) |
C9—C10—C11—C12 | 1.2 (3) | C23—C24—C25—C26 | −178.29 (19) |
C10—C11—C12—C13 | −0.3 (3) | O19—C20—C25—C24 | 174.3 (2) |
C11—C12—C13—C8 | −0.6 (3) | C21—C20—C25—C24 | −2.4 (3) |
C11—C12—C13—C14 | 178.51 (19) | O19—C20—C25—C26 | −5.9 (3) |
C7—C8—C13—C12 | 179.47 (18) | C21—C20—C25—C26 | 177.44 (19) |
C9—C8—C13—C12 | 0.5 (3) | C4—C3—C26—C25 | −107.7 (2) |
C7—C8—C13—C14 | 0.3 (3) | C2—C3—C26—C25 | 81.0 (2) |
C9—C8—C13—C14 | −178.64 (17) | C4—C3—C26—C17 | 18.1 (2) |
C6—C5—C14—O1 | −179.4 (2) | C2—C3—C26—C17 | −153.29 (17) |
C4—C5—C14—O1 | 1.4 (3) | C24—C25—C26—C3 | −28.5 (2) |
C6—C5—C14—C13 | 0.7 (3) | C20—C25—C26—C3 | 151.63 (17) |
C4—C5—C14—C13 | −178.59 (17) | C24—C25—C26—C17 | −152.88 (17) |
C2—O1—C14—C5 | 0.8 (3) | C20—C25—C26—C17 | 27.3 (2) |
C2—O1—C14—C13 | −179.22 (17) | C18—C17—C26—C3 | −177.81 (15) |
C12—C13—C14—C5 | −179.86 (19) | C16—C17—C26—C3 | −47.87 (19) |
C8—C13—C14—C5 | −0.8 (3) | C18—C17—C26—C25 | −49.28 (19) |
C12—C13—C14—O1 | 0.2 (3) | C16—C17—C26—C25 | 80.67 (18) |
C8—C13—C14—O1 | 179.27 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28A···CgAi | 0.96 | 2.60 | 3.530 (3) | 163 |
C7—H7···O29ii | 0.93 | 2.49 | 3.306 (2) | 147 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C25H20O4 |
Mr | 384.41 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 12.172 (1), 9.140 (1), 18.081 (1) |
β (°) | 106.58 (1) |
V (Å3) | 1927.9 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
|
Data collection |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3967, 3783, 2686 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.153, 1.02 |
No. of reflections | 3783 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.25 |
Selected geometric parameters (Å, º) topO1—C14 | 1.371 (2) | C16—C27 | 1.505 (3) |
O1—C2 | 1.381 (2) | C16—C28 | 1.518 (3) |
C2—O29 | 1.216 (2) | C16—C17 | 1.540 (3) |
C2—C3 | 1.427 (2) | C17—C18 | 1.522 (3) |
C3—C4 | 1.361 (2) | C17—C26 | 1.535 (3) |
C3—C26 | 1.508 (2) | C18—O19 | 1.422 (3) |
C4—O15 | 1.336 (2) | O19—C20 | 1.370 (3) |
C4—C5 | 1.443 (2) | C21—C22 | 1.370 (4) |
C5—C14 | 1.368 (2) | C25—C26 | 1.523 (3) |
O15—C16 | 1.476 (2) | | |
| | | |
C14—O1—C2 | 121.31 (14) | C5—C14—O1 | 121.47 (16) |
O29—C2—O1 | 115.36 (16) | C4—O15—C16 | 119.77 (13) |
O29—C2—C3 | 125.78 (17) | O15—C16—C27 | 106.10 (15) |
O1—C2—C3 | 118.86 (15) | O15—C16—C28 | 102.94 (15) |
O15—C4—C3 | 124.88 (16) | O19—C20—C21 | 115.4 (2) |
O15—C4—C5 | 114.00 (14) | O19—C20—C25 | 123.34 (19) |
| | | |
C26—C3—C4—C5 | −175.5 (2) | C4—O15—C16—C28 | −153.9 (2) |
C6—C5—C14—O1 | −179.4 (2) | O19—C20—C25—C24 | 174.3 (2) |
C4—O15—C16—C27 | 90.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28A···CgAi | 0.96 | 2.60 | 3.530 (3) | 163 |
C7—H7···O29ii | 0.93 | 2.49 | 3.306 (2) | 147 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+3/2, z−1/2. |
Coumarin derivatives occurring in plants have different biological activities (Cisowski, 1983, 1984). These derivatives are used in oral anticoagulation therapy (Cole et al., 1988; Greenfield, 1988). Coumarin derivatives have been found to be useful in solid state photochemical reactions (Gnanaguru et al., 1985) and in dye lasers (Masilamani, 1979). Coumarin substrates are also used in enzyme determination (Michel & Durant, 1976). The title compound, (I), a coumarin derivative was chosen for crystallographic study to determine its structure and conformation.
The title molecule (Fig. 1) consists of three benzene rings (A, B and F), one pyran ring (C) and two dihydropyran rings (D and E). The molecule contains two planar regions, one comprising of atoms in A, B, C and D rings and other containing atoms in E and F rings. The weighted least-squares planes through these two halves (excluding C17), form a dihedral angle of 62.56 (3)°. The H17—C17—C26—H26 torsion angle at the D and E ring junction is −46.6 (2)°. Both the dihydropyran rings, D and E, adopt distorted sofa conformations with a ΔCs(C17) asymmetry parameter of 0.070 (1) and 0.026 (1), respectively (Nardelli, 1983); the deviation of C17 from the C3—C4—O15—C16—C26 and C18—O19—C20—C25—C26 planes is 0.623 (2) and 0.633 (2) Å, respectively. All the C—C bond lengths in the title compound agree well with the mean values (Allen et al., 1987). The C2—O1 [1.381 (2) Å], C14—O1 [1.371 (2) Å] and C2—O29 [1.216 (2) Å] distances in the pyran ring agree well with those reported in the related structures (Chinnakali et al., 1998, 1999).
In the crystal, the inversion related molecules are linked to form dimeric pairs by mutual C—H···π interactions (Table 2), C28—H28A···CgA, where CgA is the centroid of the benzene ring A (C9—C13) of the symmetry-related molecule at (1 − x, 1 − y, −z). The dimeric pairs are interlinked by C7—H7···O29ii [symmetry code:(ii) x − 1/2, 3/2 − y, z − 1/2] hydrogen bonds along the [101] direction.