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organic compounds
In the title compound, C17H18O4, the hydroxyl and methoxyphenyl substituents are in axial positions. The heterocyclic ring adopts a half-chair conformation. The molecules are linked by O—H
O hydrogen bonds, leading to dimerization.
O hydrogen bonds, leading to dimerization.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802021852/na6188sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536802021852/na6188Isup2.hkl |
CCDC reference: 202983
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.003 Å - R factor = 0.038
- wR factor = 0.114
- Data-to-parameter ratio = 10.5
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.003 ÅcheckCIF results
No syntax errors found ADDSYM reports no extra symmetry
Computing details top
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989)'; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: PARST97 (Nardelli, 1996).
5-methoxy-4-(4-methoxyphenyl)isochroman-3-ol top
Crystal data top
| C17H18O4 | Z = 2 |
| Mr = 286.31 | F(000) = 304 |
| Triclinic, P1 | Dx = 1.327 Mg m−3 |
| Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
| a = 5.881 (2) Å | Cell parameters from 25 reflections |
| b = 8.182 (2) Å | θ = 38.2–39.9° |
| c = 15.983 (3) Å | µ = 0.77 mm−1 |
| α = 78.03 (2)° | T = 293 K |
| β = 89.28 (2)° | Plate, colourless |
| γ = 72.49 (2)° | 0.50 × 0.40 × 0.10 mm |
| V = 716.4 (3) Å3 |
Data collection top
| Rigaku AFC-5S diffractometer | 1974 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.025 |
| Graphite monochromator | θmax = 67.5°, θmin = 5.7° |
| ω scans | h = −6→7 |
| Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = −9→8 |
| Tmin = 0.775, Tmax = 0.925 | l = −19→18 |
| 2695 measured reflections | 3 standard reflections every 150 reflections |
| 2505 independent reflections | intensity decay: <2% |
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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0611P)2 + 0.0312P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.12 | (Δ/σ)max < 0.001 |
| 2505 reflections | Δρmax = 0.14 e Å−3 |
| 239 parameters | Δρmin = −0.16 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: 0.0072 (12) |
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 | ||
| O5 | 0.4012 (2) | 0.7842 (2) | 0.26632 (8) | 0.0563 (3) | |
| O44 | 0.1654 (3) | 0.1775 (2) | 0.50818 (8) | 0.0727 (4) | |
| O2 | −0.1054 (2) | 0.5794 (2) | 0.09372 (7) | 0.0524 (3) | |
| C4 | 0.2301 (3) | 0.5864 (2) | 0.1795 (1) | 0.0404 (4) | |
| O30 | 0.2557 (2) | 0.5838 (2) | 0.03253 (8) | 0.0615 (4) | |
| C5 | 0.1976 (3) | 0.8774 (2) | 0.2170 (1) | 0.0447 (4) | |
| C10 | 0.1042 (3) | 0.7802 (2) | 0.17159 (9) | 0.0405 (4) | |
| C9 | −0.1019 (3) | 0.8644 (2) | 0.1199 (1) | 0.0474 (4) | |
| C43 | −0.0392 (3) | 0.3941 (2) | 0.3814 (2) | 0.0507 (4) | |
| C41 | 0.2025 (3) | 0.4765 (2) | 0.26617 (9) | 0.0386 (4) | |
| C42 | −0.0174 (3) | 0.4913 (2) | 0.3012 (2) | 0.0461 (4) | |
| C46 | 0.4012 (3) | 0.3561 (2) | 0.3135 (2) | 0.0483 (4) | |
| C45 | 0.3833 (3) | 0.2579 (2) | 0.3927 (2) | 0.0539 (5) | |
| C7 | −0.1205 (4) | 1.1359 (2) | 0.1583 (2) | 0.0599 (5) | |
| C44 | 0.1624 (3) | 0.2786 (2) | 0.4282 (1) | 0.0502 (4) | |
| C1 | −0.2043 (4) | 0.7663 (3) | 0.0684 (2) | 0.0565 (5) | |
| C3 | 0.1491 (3) | 0.5222 (2) | 0.1053 (1) | 0.0471 (4) | |
| C6 | 0.0841 (4) | 1.0554 (2) | 0.2108 (2) | 0.0549 (5) | |
| C8 | −0.2143 (4) | 1.0440 (2) | 0.1133 (2) | 0.0593 (5) | |
| C50 | 0.5063 (4) | 0.8753 (3) | 0.3137 (2) | 0.0667 (6) | |
| H51 | 0.3900 | 0.9332 | 0.3493 | 0.100* | |
| H52 | 0.5598 | 0.9607 | 0.2748 | 0.100* | |
| H53 | 0.6397 | 0.7932 | 0.3490 | 0.100* | |
| C440 | −0.0518 (4) | 0.2010 (4) | 0.5503 (2) | 0.0837 (7) | |
| H441 | −0.1626 | 0.1678 | 0.5189 | 0.126* | |
| H442 | −0.1178 | 0.3219 | 0.5535 | 0.126* | |
| H443 | −0.0222 | 0.1291 | 0.6071 | 0.126* | |
| H3 | 0.205 (3) | 0.390 (2) | 0.1143 (9) | 0.035 (4)* | |
| H4 | 0.399 (3) | 0.569 (2) | 0.173 (2) | 0.048 (5)* | |
| H7 | −0.199 (4) | 1.256 (3) | 0.153 (2) | 0.068 (6)* | |
| H45 | 0.524 (3) | 0.169 (2) | 0.427 (2) | 0.066 (6)* | |
| H42 | −0.155 (3) | 0.573 (2) | 0.267 (2) | 0.053 (5)* | |
| H46 | 0.551 (3) | 0.342 (2) | 0.290 (2) | 0.059 (5)* | |
| H43 | −0.199 (4) | 0.412 (2) | 0.403 (2) | 0.064 (5)* | |
| H6 | 0.144 (3) | 1.123 (2) | 0.244 (2) | 0.060 (5)* | |
| H8 | −0.358 (4) | 1.102 (3) | 0.073 (2) | 0.077 (6)* | |
| H11 | −0.182 (3) | 0.805 (2) | 0.006 (2) | 0.053 (5)* | |
| H12 | −0.381 (4) | 0.790 (3) | 0.076 (2) | 0.077 (6)* | |
| H30 | 0.222 (5) | 0.529 (4) | −0.012 (2) | 0.125 (10)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O5 | 0.0567 (7) | 0.0528 (7) | 0.0653 (8) | −0.0206 (6) | −0.0099 (6) | −0.0190 (6) |
| O44 | 0.0834 (10) | 0.0867 (10) | 0.0458 (7) | −0.0412 (8) | −0.0100 (7) | 0.0139 (7) |
| O2 | 0.0580 (7) | 0.0606 (7) | 0.0450 (7) | −0.0269 (6) | −0.0026 (5) | −0.0116 (5) |
| C4 | 0.0412 (9) | 0.0416 (8) | 0.0409 (8) | −0.0161 (7) | 0.0028 (6) | −0.0092 (6) |
| O30 | 0.0781 (9) | 0.0713 (9) | 0.0437 (7) | −0.0335 (7) | 0.0149 (6) | −0.0156 (6) |
| C5 | 0.0529 (10) | 0.0414 (8) | 0.0422 (8) | −0.0201 (7) | 0.0070 (7) | −0.0063 (6) |
| C10 | 0.0466 (9) | 0.0396 (8) | 0.0355 (8) | −0.0166 (7) | 0.0044 (6) | −0.0038 (6) |
| C9 | 0.0536 (10) | 0.0482 (9) | 0.0372 (8) | −0.0162 (7) | 0.0021 (7) | −0.0009 (7) |
| C43 | 0.0495 (10) | 0.0578 (10) | 0.0456 (9) | −0.0219 (8) | 0.0034 (7) | −0.0048 (8) |
| C41 | 0.0437 (9) | 0.0350 (7) | 0.0387 (8) | −0.0134 (6) | −0.0007 (6) | −0.0095 (6) |
| C42 | 0.0420 (9) | 0.0467 (9) | 0.0459 (9) | −0.0119 (7) | −0.0013 (7) | −0.0037 (7) |
| C46 | 0.0402 (9) | 0.0515 (10) | 0.0516 (10) | −0.0128 (7) | −0.0021 (7) | −0.0091 (7) |
| C45 | 0.0521 (11) | 0.0532 (10) | 0.0503 (10) | −0.0142 (8) | −0.0134 (8) | 0.0004 (8) |
| C7 | 0.0785 (13) | 0.0371 (9) | 0.0571 (11) | −0.0130 (9) | 0.0112 (10) | −0.0017 (8) |
| C44 | 0.0632 (11) | 0.0507 (9) | 0.0408 (9) | −0.0286 (8) | −0.0068 (8) | −0.0011 (7) |
| C1 | 0.0586 (12) | 0.0623 (11) | 0.0452 (10) | −0.0179 (9) | −0.0081 (8) | −0.0043 (8) |
| C3 | 0.0575 (10) | 0.0480 (9) | 0.0405 (8) | −0.0213 (8) | 0.0049 (7) | −0.0120 (7) |
| C6 | 0.0760 (13) | 0.0416 (9) | 0.0515 (10) | −0.0254 (9) | 0.0099 (9) | −0.0089 (8) |
| C8 | 0.0635 (12) | 0.0500 (10) | 0.0511 (10) | −0.0084 (9) | −0.0007 (9) | 0.0051 (8) |
| C50 | 0.0651 (12) | 0.0781 (14) | 0.0747 (13) | −0.0354 (11) | 0.0015 (10) | −0.0354 (11) |
| C440 | 0.0951 (17) | 0.1218 (19) | 0.0488 (11) | −0.0702 (15) | 0.0008 (11) | 0.0055 (12) |
Geometric parameters (Å, º) top
| O5—C5 | 1.364 (2) | C41—C46 | 1.389 (2) |
| O5—C50 | 1.426 (2) | C42—H42 | 0.964 (19) |
| O44—C44 | 1.368 (2) | C46—C45 | 1.373 (2) |
| O44—C440 | 1.416 (3) | C46—H46 | 0.935 (18) |
| O2—C3 | 1.429 (2) | C45—C44 | 1.388 (3) |
| O2—C1 | 1.434 (2) | C45—H45 | 1.00 (2) |
| C4—C10 | 1.513 (2) | C7—C8 | 1.368 (3) |
| C4—C41 | 1.523 (2) | C7—C6 | 1.380 (3) |
| C4—C3 | 1.528 (2) | C7—H7 | 0.94 (2) |
| C4—H4 | 0.967 (17) | C1—H11 | 0.995 (19) |
| O30—C3 | 1.389 (2) | C1—H12 | 1.01 (2) |
| O30—H30 | 0.97 (3) | C3—H3 | 1.009 (15) |
| C5—C6 | 1.391 (2) | C6—H6 | 0.98 (2) |
| C5—C10 | 1.405 (2) | C8—H8 | 1.01 (2) |
| C10—C9 | 1.382 (2) | C50—H51 | 0.9600 |
| C9—C8 | 1.400 (2) | C50—H52 | 0.9600 |
| C9—C1 | 1.505 (2) | C50—H53 | 0.9600 |
| C43—C44 | 1.383 (2) | C440—H441 | 0.9600 |
| C43—C42 | 1.389 (2) | C440—H442 | 0.9600 |
| C43—H43 | 0.98 (2) | C440—H443 | 0.9600 |
| C41—C42 | 1.384 (2) | ||
| C5—O5—C50 | 118.0 (2) | C8—C7—H7 | 118.4 (13) |
| C44—O44—C440 | 118.1 (2) | C6—C7—H7 | 120.2 (13) |
| C3—O2—C1 | 113.0 (2) | O44—C44—C43 | 125.5 (2) |
| C10—C4—C41 | 112.8 (2) | O44—C44—C45 | 115.3 (2) |
| C10—C4—C3 | 110.4 (2) | C43—C44—C45 | 119.1 (2) |
| C41—C4—C3 | 112.1 (2) | O2—C1—C9 | 113.6 (2) |
| C10—C4—H4 | 109.0 (10) | O2—C1—H11 | 109.8 (10) |
| C41—C4—H4 | 107.0 (10) | C9—C1—H11 | 109.9 (10) |
| C3—C4—H4 | 105.2 (10) | O2—C1—H12 | 104.5 (12) |
| C3—O30—H30 | 107.3 (18) | C9—C1—H12 | 111.0 (12) |
| O5—C5—C6 | 124.2 (2) | H11—C1—H12 | 107.8 (16) |
| O5—C5—C10 | 115.2 (2) | O30—C3—O2 | 111.8 (2) |
| C6—C5—C10 | 120.6 (2) | O30—C3—C4 | 107.7 (2) |
| C9—C10—C5 | 119.0 (2) | O2—C3—C4 | 111.0 (2) |
| C9—C10—C4 | 121.2 (2) | O30—C3—H3 | 106.1 (8) |
| C5—C10—C4 | 119.8 (2) | O2—C3—H3 | 107.8 (9) |
| C10—C9—C8 | 120.1 (2) | C4—C3—H3 | 112.4 (9) |
| C10—C9—C1 | 120.7 (2) | C7—C6—C5 | 118.9 (2) |
| C8—C9—C1 | 119.1 (2) | C7—C6—H6 | 120.0 (11) |
| C44—C43—C42 | 119.8 (2) | C5—C6—H6 | 121.0 (11) |
| C44—C43—H43 | 122.2 (12) | C7—C8—C9 | 119.9 (2) |
| C42—C43—H43 | 118.0 (12) | C7—C8—H8 | 122.3 (12) |
| C42—C41—C46 | 117.2 (2) | C9—C8—H8 | 117.7 (12) |
| C42—C41—C4 | 122.3 (2) | O5—C50—H51 | 109.5 |
| C46—C41—C4 | 120.5 (2) | O5—C50—H52 | 109.5 |
| C41—C42—C43 | 121.7 (2) | H51—C50—H52 | 109.5 |
| C41—C42—H42 | 116.8 (10) | O5—C50—H53 | 109.5 |
| C43—C42—H42 | 121.5 (11) | H51—C50—H53 | 109.5 |
| C45—C46—C41 | 121.9 (2) | H52—C50—H53 | 109.5 |
| C45—C46—H46 | 119.4 (11) | O44—C440—H441 | 109.5 |
| C41—C46—H46 | 118.6 (11) | O44—C440—H442 | 109.5 |
| C46—C45—C44 | 120.1 (2) | H441—C440—H442 | 109.5 |
| C46—C45—H45 | 122.9 (11) | O44—C440—H443 | 109.5 |
| C44—C45—H45 | 117.0 (11) | H441—C440—H443 | 109.5 |
| C8—C7—C6 | 121.4 (2) | H442—C440—H443 | 109.5 |
| C50—O5—C5—C6 | −0.8 (2) | C41—C46—C45—C44 | −0.7 (3) |
| C50—O5—C5—C10 | 179.6 (2) | C440—O44—C44—C43 | −5.1 (3) |
| O5—C5—C10—C9 | −180.0 (2) | C440—O44—C44—C45 | 175.9 (2) |
| C6—C5—C10—C9 | 0.4 (2) | C42—C43—C44—O44 | 179.0 (2) |
| O5—C5—C10—C4 | −0.2 (2) | C42—C43—C44—C45 | −2.0 (3) |
| C6—C5—C10—C4 | −179.8 (2) | C46—C45—C44—O44 | −178.5 (2) |
| C41—C4—C10—C9 | −108.2 (2) | C46—C45—C44—C43 | 2.4 (3) |
| C3—C4—C10—C9 | 18.0 (2) | C3—O2—C1—C9 | −46.0 (2) |
| C41—C4—C10—C5 | 72.1 (2) | C10—C9—C1—O2 | 14.2 (2) |
| C3—C4—C10—C5 | −161.7 (2) | C8—C9—C1—O2 | −167.7 (2) |
| C5—C10—C9—C8 | 0.2 (2) | C1—O2—C3—O30 | −55.5 (2) |
| C4—C10—C9—C8 | −179.6 (2) | C1—O2—C3—C4 | 64.8 (2) |
| C5—C10—C9—C1 | 178.3 (2) | C10—C4—C3—O30 | 74.4 (2) |
| C4—C10—C9—C1 | −1.4 (2) | C41—C4—C3—O30 | −159.0 (2) |
| C10—C4—C41—C42 | 50.1 (2) | C10—C4—C3—O2 | −48.4 (2) |
| C3—C4—C41—C42 | −75.1 (2) | C41—C4—C3—O2 | 78.2 (2) |
| C10—C4—C41—C46 | −129.7 (2) | C8—C7—C6—C5 | 0.7 (3) |
| C3—C4—C41—C46 | 105.0 (2) | O5—C5—C6—C7 | 179.6 (2) |
| C46—C41—C42—C43 | 1.8 (2) | C10—C5—C6—C7 | −0.8 (2) |
| C4—C41—C42—C43 | −178.0 (2) | C6—C7—C8—C9 | −0.1 (3) |
| C44—C43—C42—C41 | −0.2 (3) | C10—C9—C8—C7 | −0.3 (3) |
| C42—C41—C46—C45 | −1.4 (2) | C1—C9—C8—C7 | −178.5 (2) |
| C4—C41—C46—C45 | 178.5 (2) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O30—H30···O2i | 0.97 (4) | 1.96 (4) | 2.917 (2) | 170 (3) |
| Symmetry code: (i) −x, −y+1, −z. |
