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The title compound, C18H16O3, crystallizes with one mol­ecule in the asymmetric unit. The conformation of the dihydro­pyran ring features puckering of the O atom by 0.612 (2) Å from the least-squares plane defined by the five C atoms [maximum deviation 0.1025 (12) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003194/bh2073sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003194/bh2073Isup2.hkl
Contains datablock I

CCDC reference: 636849

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.125
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT148_ALERT_3_B su on the b - Axis is Too Large (x 1000) . 10 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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: X-SEED (Barbour, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(RS)-2-(3,4-Methylenedioxyphenyl)-5-phenyl-3,6-dihydro-2H-pyran top
Crystal data top
C18H16O3Z = 2
Mr = 280.31F(000) = 296
Triclinic, P1Dx = 1.358 Mg m3
Hall symbol: -P 1Melting point = 425–427 K
a = 6.6380 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.911 (10) ÅCell parameters from 25 reflections
c = 13.498 (5) Åθ = 9.8–15.7°
α = 81.24 (5)°µ = 0.09 mm1
β = 80.21 (2)°T = 298 K
γ = 82.05 (4)°Plate, colourless
V = 685.7 (9) Å30.55 × 0.45 × 0.10 mm
Data collection top
Enraf–Nonius TurboCAD-4
diffractometer
Rint = 0.019
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 1.5°
Graphite monochromatorh = 77
non–profiled ω/2θ scansk = 99
2750 measured reflectionsl = 116
2413 independent reflections3 standard reflections every 60 min
1932 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0716P)2 + 0.1555P]
where P = (Fo2 + 2Fc2)/3
2413 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 2.48 (2H, m), 4.53 (1H, dd, J 9.6, 4.2 Hz), 4.71 (2H, m), 5.95 (2H, s), 6.25 (1H, m), 6.80 (1H, d, J 7.8 Hz), 6.88 (1H, dd, J 7.8, 1.8 Hz), 6.94 (1H, d, J 1.8 Hz), 2.26–7.36 (5H, m); 13C NMR (75 MHz, CDCl3, δ, p.p.m.): 33.3, 68.1, 75.7, 101.2, 106.9, 108.4, 119.7, 121.6, 125.1, 127.8, 128.8, 136.2, 136.4, 138.3, 147.2, 148.0; IR: 1659, 1589, 1489, 1253, 1027, 1018, 777 cm-1.

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.9500 (0.0064) x + 6.4392 (0.0087) y + 6.8342 (0.0120) z = 6.3962 (0.0092)

* 0.0022 (0.0012) C6 * -0.0006 (0.0013) C7 * -0.0011 (0.0014) C8 * 0.0013 (0.0013) C9 * 0.0004 (0.0013) C10 * -0.0021 (0.0012) C11 - 0.0449 (0.0028) C2

Rms deviation of fitted atoms = 0.0015

1.7907 (0.0066) x + 7.7170 (0.0096) y + 4.5601 (0.0110) z = 6.6670 (0.0084)

Angle to previous plane (with approximate e.s.d.) = 23.79 (0.11)

* -0.0757 (0.0009) C1 * 0.0516 (0.0012) C2 * 0.0354 (0.0012) C3 * -0.1025 (0.0012) C4 * 0.0911 (0.0010) C5 - 0.6124 (0.0023) O1 0.1831 (0.0027) C6

Rms deviation of fitted atoms = 0.0754

- 3.7458 (0.0061) x + 5.8458 (0.0082) y - 0.2828 (0.0099) z = 3.7265 (0.0060)

Angle to previous plane (with approximate e.s.d.) = 51.43 (0.09)

* 0.0032 (0.0012) C12 * -0.0086 (0.0012) C13 * 0.0065 (0.0012) C14 * 0.0011 (0.0013) C15 * -0.0065 (0.0014) C16 * 0.0042 (0.0013) C17 0.0353 (0.0027) C5 0.2559 (0.0029) O1 - 0.0026 (0.0026) O2 0.1730 (0.0033) C18

Rms deviation of fitted atoms = 0.0056

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.12451 (18)0.76062 (18)0.00835 (9)0.0472 (4)
O20.3421 (2)0.43061 (19)0.26385 (10)0.0561 (4)
O30.2820 (2)0.47454 (18)0.42096 (9)0.0501 (4)
C10.2124 (3)0.8621 (3)0.09679 (13)0.0433 (4)
H1A0.16730.98260.09110.052*
H1B0.16230.83410.15510.052*
C20.4443 (2)0.8350 (2)0.11424 (12)0.0330 (4)
C30.5435 (3)0.7648 (2)0.03782 (13)0.0389 (4)
H30.68650.74870.04970.047*
C40.4361 (3)0.7101 (2)0.06656 (13)0.0390 (4)
H4A0.50100.75140.11600.047*
H4B0.44870.58540.07970.047*
C50.2089 (3)0.7812 (2)0.07803 (13)0.0374 (4)
H50.19860.90470.08240.045*
C60.5468 (2)0.8896 (2)0.21797 (12)0.0329 (4)
C70.7398 (3)0.8116 (2)0.25646 (14)0.0441 (4)
H70.80830.72550.21520.053*
C80.8311 (3)0.8596 (3)0.35456 (15)0.0511 (5)
H80.95990.80590.37860.061*
C90.7324 (3)0.9872 (2)0.41739 (14)0.0471 (5)
H90.79421.01980.48350.057*
C100.5415 (3)1.0654 (2)0.38087 (13)0.0424 (4)
H100.47421.15130.42270.051*
C110.4492 (3)1.0180 (2)0.28316 (13)0.0372 (4)
H110.31991.07200.26000.045*
C120.0809 (2)0.6982 (2)0.17137 (13)0.0347 (4)
C130.0727 (3)0.5973 (2)0.16350 (12)0.0358 (4)
H130.09680.57590.10090.043*
C140.1849 (3)0.5323 (2)0.25207 (13)0.0351 (4)
C150.1496 (3)0.5585 (2)0.34539 (12)0.0364 (4)
C160.0009 (3)0.6542 (3)0.35537 (14)0.0470 (5)
H160.02590.67120.41870.056*
C170.1148 (3)0.7246 (3)0.26592 (14)0.0455 (5)
H170.21700.79160.26990.055*
C180.4219 (3)0.4145 (3)0.36833 (14)0.0529 (5)
H18A0.43870.29500.39380.063*
H18B0.55550.48200.37900.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0376 (7)0.0680 (9)0.0360 (7)0.0203 (6)0.0051 (5)0.0057 (6)
O20.0633 (9)0.0691 (9)0.0419 (8)0.0418 (8)0.0004 (6)0.0042 (6)
O30.0517 (8)0.0635 (9)0.0346 (7)0.0245 (6)0.0012 (6)0.0023 (6)
C10.0336 (9)0.0572 (11)0.0338 (9)0.0041 (8)0.0020 (7)0.0061 (8)
C20.0322 (8)0.0272 (8)0.0384 (9)0.0047 (6)0.0019 (7)0.0037 (6)
C30.0295 (8)0.0406 (10)0.0440 (10)0.0031 (7)0.0030 (7)0.0014 (8)
C40.0349 (9)0.0416 (9)0.0385 (9)0.0037 (7)0.0061 (7)0.0013 (7)
C50.0354 (9)0.0385 (9)0.0378 (9)0.0086 (7)0.0047 (7)0.0005 (7)
C60.0327 (8)0.0291 (8)0.0375 (9)0.0091 (6)0.0028 (7)0.0040 (7)
C70.0395 (10)0.0390 (10)0.0475 (10)0.0021 (8)0.0013 (8)0.0026 (8)
C80.0405 (10)0.0524 (12)0.0536 (12)0.0038 (9)0.0089 (9)0.0046 (9)
C90.0508 (11)0.0517 (11)0.0373 (10)0.0189 (9)0.0053 (8)0.0026 (8)
C100.0483 (10)0.0418 (10)0.0375 (9)0.0112 (8)0.0091 (8)0.0017 (8)
C110.0349 (9)0.0366 (9)0.0394 (9)0.0054 (7)0.0037 (7)0.0044 (7)
C120.0309 (8)0.0338 (9)0.0376 (9)0.0049 (7)0.0042 (7)0.0002 (7)
C130.0368 (9)0.0393 (9)0.0320 (9)0.0069 (7)0.0050 (7)0.0046 (7)
C140.0345 (8)0.0321 (8)0.0387 (9)0.0088 (7)0.0044 (7)0.0016 (7)
C150.0382 (9)0.0360 (9)0.0326 (9)0.0064 (7)0.0004 (7)0.0005 (7)
C160.0515 (11)0.0578 (12)0.0355 (10)0.0185 (9)0.0074 (8)0.0061 (8)
C170.0448 (10)0.0525 (11)0.0430 (10)0.0210 (9)0.0069 (8)0.0044 (8)
C180.0541 (11)0.0632 (12)0.0423 (11)0.0271 (10)0.0014 (9)0.0011 (9)
Geometric parameters (Å, º) top
O1—C51.416 (2)C7—C81.379 (3)
O1—C11.418 (2)C7—H70.9300
O2—C141.377 (2)C8—C91.383 (3)
O2—C181.413 (2)C8—H80.9300
O3—C151.380 (2)C9—C101.377 (3)
O3—C181.429 (2)C9—H90.9300
C1—C21.508 (2)C10—C111.376 (2)
C1—H1A0.9700C10—H100.9300
C1—H1B0.9700C11—H110.9300
C2—C31.327 (2)C12—C171.384 (3)
C2—C61.477 (2)C12—C131.405 (2)
C3—C41.496 (2)C13—C141.365 (2)
C3—H30.9300C13—H130.9300
C4—C51.525 (2)C14—C151.370 (2)
C4—H4A0.9700C15—C161.369 (3)
C4—H4B0.9700C16—C171.393 (3)
C5—C121.509 (2)C16—H160.9300
C5—H50.9800C17—H170.9300
C6—C71.395 (2)C18—H18A0.9700
C6—C111.402 (3)C18—H18B0.9700
C5—O1—C1111.78 (14)C9—C8—H8119.8
C14—O2—C18105.40 (14)C10—C9—C8119.15 (17)
C15—O3—C18104.49 (13)C10—C9—H9120.4
O1—C1—C2113.01 (14)C8—C9—H9120.4
O1—C1—H1A109.0C11—C10—C9120.73 (17)
C2—C1—H1A109.0C11—C10—H10119.6
O1—C1—H1B109.0C9—C10—H10119.6
C2—C1—H1B109.0C10—C11—C6121.10 (16)
H1A—C1—H1B107.8C10—C11—H11119.4
C3—C2—C6124.15 (15)C6—C11—H11119.4
C3—C2—C1119.37 (15)C17—C12—C13119.90 (16)
C6—C2—C1116.48 (14)C17—C12—C5118.96 (15)
C2—C3—C4123.14 (16)C13—C12—C5121.13 (15)
C2—C3—H3118.4C14—C13—C12116.84 (16)
C4—C3—H3118.4C14—C13—H13121.6
C3—C4—C5110.94 (14)C12—C13—H13121.6
C3—C4—H4A109.5C13—C14—C15122.82 (16)
C5—C4—H4A109.5C13—C14—O2127.56 (16)
C3—C4—H4B109.5C15—C14—O2109.60 (15)
C5—C4—H4B109.5C16—C15—C14121.57 (16)
H4A—C4—H4B108.0C16—C15—O3128.26 (16)
O1—C5—C12108.62 (14)C14—C15—O3110.16 (15)
O1—C5—C4110.16 (14)C15—C16—C17116.61 (17)
C12—C5—C4113.69 (14)C15—C16—H16121.7
O1—C5—H5108.1C17—C16—H16121.7
C12—C5—H5108.1C12—C17—C16122.24 (17)
C4—C5—H5108.1C12—C17—H17118.9
C7—C6—C11117.30 (16)C16—C17—H17118.9
C7—C6—C2121.72 (15)O2—C18—O3108.62 (15)
C11—C6—C2120.93 (15)O2—C18—H18A110.0
C8—C7—C6121.23 (17)O3—C18—H18A110.0
C8—C7—H7119.4O2—C18—H18B110.0
C6—C7—H7119.4O3—C18—H18B110.0
C7—C8—C9120.49 (18)H18A—C18—H18B108.3
C7—C8—H8119.8
C5—O1—C1—C252.1 (2)C4—C5—C12—C1766.7 (2)
O1—C1—C2—C318.6 (2)O1—C5—C12—C138.9 (2)
O1—C1—C2—C6161.16 (15)C4—C5—C12—C13114.15 (19)
C6—C2—C3—C4179.84 (16)C17—C12—C13—C141.2 (2)
C1—C2—C3—C40.1 (3)C5—C12—C13—C14177.91 (15)
C2—C3—C4—C512.5 (2)C12—C13—C14—C151.5 (3)
C1—O1—C5—C12169.10 (13)C12—C13—C14—O2179.89 (16)
C1—O1—C5—C465.77 (19)C18—O2—C14—C13173.58 (18)
C3—C4—C5—O144.0 (2)C18—O2—C14—C157.9 (2)
C3—C4—C5—C12166.21 (15)C13—C14—C15—C160.7 (3)
C3—C2—C6—C727.5 (3)O2—C14—C15—C16179.28 (16)
C1—C2—C6—C7152.24 (17)C13—C14—C15—O3178.46 (15)
C3—C2—C6—C11155.07 (17)O2—C14—C15—O30.2 (2)
C1—C2—C6—C1125.2 (2)C18—O3—C15—C16172.9 (2)
C11—C6—C7—C80.3 (3)C18—O3—C15—C148.0 (2)
C2—C6—C7—C8177.82 (17)C14—C15—C16—C170.6 (3)
C6—C7—C8—C90.0 (3)O3—C15—C16—C17179.53 (17)
C7—C8—C9—C100.2 (3)C13—C12—C17—C160.0 (3)
C8—C9—C10—C110.0 (3)C5—C12—C17—C16179.13 (17)
C9—C10—C11—C60.3 (3)C15—C16—C17—C120.9 (3)
C7—C6—C11—C100.5 (2)C14—O2—C18—O312.9 (2)
C2—C6—C11—C10177.99 (16)C15—O3—C18—O212.9 (2)
O1—C5—C12—C17170.23 (16)
 

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