In the title compound, C
18H
20O
5, the hydroxyl and dimethoxyphenyl substituents are in axial positions. The heterocyclic ring is in a half-chair conformation. The molecules are linked by O—H
O hydrogen bonds, leading to the formation of a chain extended throughout the whole of the crystal.
Supporting information
CCDC reference: 189374
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.109
- Data-to-parameter ratio = 14.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 72.57
From the CIF: _reflns_number_total 3063
Count of symmetry unique reflns 1836
Completeness (_total/calc) 166.83%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1227
Fraction of Friedel pairs measured 0.668
Are heavy atom types Z>Si present no
Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1989a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989b)'; 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).
(3
S,4
R)-4-(2,5-Dimethoxyphenyl)-8-methoxyisochroman-3-ol
top
Crystal data top
C18H20O5 | F(000) = 672 |
Mr = 316.34 | Dx = 1.318 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 20 reflections |
a = 11.920 (1) Å | θ = 9.5–12.3° |
b = 18.114 (2) Å | µ = 0.79 mm−1 |
c = 7.383 (1) Å | T = 293 K |
V = 1594.2 (3) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.28 × 0.18 mm |
Data collection top
Rigaku AFC-5S diffractometer | 2599 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 72.6°, θmin = 4.4° |
ω scans | h = −14→14 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = −22→22 |
Tmin = 0.778, Tmax = 0.879 | l = −8→8 |
6547 measured reflections | 3 standard reflections every 150 reflections |
3063 independent reflections | intensity decay: <2% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.17 e Å−3 |
3063 reflections | Δρmin = −0.15 e Å−3 |
217 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0125 (9) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1281 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.1 (2) |
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 | |
O2 | 1.1501 (1) | 0.01833 (7) | 0.0334 (2) | 0.0657 (4) | |
O80 | 0.9614 (2) | −0.12493 (9) | −0.2710 (2) | 0.0781 (5) | |
O45 | 0.8356 (2) | 0.22429 (8) | −0.0959 (2) | 0.0714 (4) | |
C42 | 0.9993 (2) | 0.15836 (9) | 0.3733 (3) | 0.0526 (5) | |
C8 | 0.9112 (2) | −0.09971 (9) | −0.1162 (3) | 0.0504 (4) | |
C44 | 0.9112 (2) | 0.25600 (9) | 0.2037 (3) | 0.0588 (5) | |
H44 | 0.8888 | 0.3050 | 0.1946 | 0.071* | |
O3 | 1.1653 (2) | −0.05244 (7) | 0.2958 (3) | 0.0793 (6) | |
C9 | 0.9786 (2) | −0.05428 (9) | −0.0090 (3) | 0.0506 (4) | |
C7 | 0.8033 (2) | −0.1174 (1) | −0.0656 (3) | 0.0527 (4) | |
H7 | 0.7596 | −0.1484 | −0.1370 | 0.063* | |
C46 | 0.9208 (2) | 0.13320 (9) | 0.0824 (3) | 0.0501 (4) | |
H46 | 0.9058 | 0.1005 | −0.0118 | 0.060* | |
C10 | 0.9351 (2) | −0.02468 (8) | 0.1487 (3) | 0.0448 (4) | |
C41 | 0.9737 (2) | 0.10775 (8) | 0.2357 (3) | 0.0460 (4) | |
C5 | 0.8247 (2) | −0.04151 (9) | 0.1991 (3) | 0.0503 (4) | |
H5 | 0.7945 | −0.0211 | 0.3040 | 0.060* | |
C6 | 0.7607 (2) | −0.0880 (1) | 0.0943 (3) | 0.0546 (5) | |
H6 | 0.6882 | −0.0999 | 0.1306 | 0.066* | |
O42 | 1.0541 (2) | 0.12912 (7) | 0.5193 (2) | 0.0711 (4) | |
C3 | 1.1301 (2) | 0.01558 (9) | 0.2237 (4) | 0.0581 (5) | |
H3 | 1.1779 (14) | 0.0590 (9) | 0.274 (3) | 0.042 (5)* | |
C45 | 0.8890 (2) | 0.2074 (1) | 0.0652 (3) | 0.0543 (5) | |
C1 | 1.0973 (2) | −0.0404 (2) | −0.0658 (4) | 0.0708 (6) | |
H11 | 1.1405 | −0.0853 | −0.0491 | 0.085* | |
H12 | 1.0985 | −0.0283 | −0.1938 | 0.085* | |
C43 | 0.9670 (2) | 0.2316 (1) | 0.3569 (3) | 0.0608 (5) | |
H43 | 0.9831 | 0.2647 | 0.4497 | 0.073* | |
C4 | 1.0053 (2) | 0.02722 (8) | 0.2617 (3) | 0.0491 (4) | |
H4 | 0.9921 | 0.0149 | 0.3892 | 0.059* | |
C80 | 0.8911 (2) | −0.14799 (15) | −0.4157 (3) | 0.0745 (6) | |
H801 | 0.8306 | −0.1135 | −0.4298 | 0.112* | |
H802 | 0.8613 | −0.1960 | −0.3894 | 0.112* | |
H803 | 0.9340 | −0.1500 | −0.5256 | 0.112* | |
C420 | 1.0894 (2) | 0.1770 (2) | 0.6598 (4) | 0.0860 (8) | |
H421 | 1.0254 | 0.2020 | 0.7095 | 0.129* | |
H422 | 1.1411 | 0.2127 | 0.6119 | 0.129* | |
H423 | 1.1256 | 0.1488 | 0.7531 | 0.129* | |
C450 | 0.7891 (2) | 0.2957 (2) | −0.1159 (4) | 0.0775 (7) | |
H451 | 0.8469 | 0.3321 | −0.1000 | 0.116* | |
H452 | 0.7317 | 0.3031 | −0.0265 | 0.116* | |
H453 | 0.7572 | 0.3006 | −0.2347 | 0.116* | |
H30 | 1.233 (3) | −0.0449 (16) | 0.370 (4) | 0.129 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0424 (6) | 0.0627 (8) | 0.0921 (12) | −0.0108 (5) | 0.0082 (7) | −0.0173 (8) |
O80 | 0.0534 (7) | 0.1005 (11) | 0.0805 (11) | 0.0015 (7) | 0.0040 (8) | −0.0433 (10) |
O45 | 0.0870 (10) | 0.0607 (8) | 0.0666 (10) | 0.0143 (7) | −0.0033 (8) | 0.0149 (7) |
C42 | 0.0513 (9) | 0.0455 (8) | 0.0609 (13) | −0.0025 (7) | −0.0049 (9) | −0.0046 (9) |
C8 | 0.0452 (8) | 0.0471 (8) | 0.0591 (12) | 0.0050 (7) | −0.0014 (8) | −0.0101 (8) |
C44 | 0.0601 (10) | 0.0384 (8) | 0.0780 (15) | 0.0010 (8) | 0.0097 (10) | 0.0005 (9) |
O3 | 0.0660 (8) | 0.0465 (7) | 0.1254 (16) | 0.0066 (6) | −0.0321 (10) | −0.0052 (8) |
C9 | 0.0396 (8) | 0.0468 (8) | 0.0655 (12) | −0.0008 (6) | 0.0022 (8) | −0.0090 (8) |
C7 | 0.0447 (8) | 0.0488 (8) | 0.0645 (12) | −0.0032 (7) | −0.0073 (8) | −0.0042 (9) |
C46 | 0.0499 (8) | 0.0455 (9) | 0.0548 (11) | 0.0002 (6) | 0.0037 (8) | −0.0014 (8) |
C10 | 0.0404 (7) | 0.0377 (7) | 0.0562 (10) | 0.0002 (6) | −0.0046 (7) | −0.0011 (7) |
C41 | 0.0413 (7) | 0.0385 (7) | 0.0581 (11) | −0.0027 (6) | 0.0002 (8) | −0.0031 (8) |
C5 | 0.0474 (9) | 0.0500 (9) | 0.0534 (12) | −0.0056 (7) | 0.0045 (8) | 0.0009 (8) |
C6 | 0.0429 (8) | 0.0595 (10) | 0.0615 (12) | −0.0093 (7) | 0.0000 (9) | 0.0027 (9) |
O42 | 0.0864 (10) | 0.0568 (8) | 0.0701 (10) | 0.0028 (7) | −0.0267 (8) | −0.0144 (7) |
C3 | 0.0456 (8) | 0.0445 (9) | 0.0841 (16) | −0.0004 (7) | −0.0088 (9) | −0.0070 (9) |
C45 | 0.0529 (9) | 0.0468 (9) | 0.0632 (13) | 0.0011 (7) | 0.0040 (9) | 0.0092 (9) |
C1 | 0.0457 (9) | 0.0755 (13) | 0.0912 (17) | −0.0088 (9) | 0.0072 (11) | −0.0274 (13) |
C43 | 0.0657 (11) | 0.0441 (8) | 0.0726 (14) | −0.0041 (8) | 0.0027 (11) | −0.0125 (9) |
C4 | 0.0480 (8) | 0.0392 (7) | 0.0600 (11) | −0.0029 (6) | −0.0046 (8) | −0.0020 (8) |
C80 | 0.0745 (13) | 0.0913 (15) | 0.0575 (14) | 0.0126 (12) | −0.0053 (11) | −0.0119 (13) |
C420 | 0.1020 (18) | 0.0801 (15) | 0.0758 (17) | −0.0053 (13) | −0.0226 (15) | −0.0271 (14) |
C450 | 0.0741 (12) | 0.0619 (12) | 0.0966 (19) | 0.0093 (10) | −0.0005 (14) | 0.0286 (13) |
Geometric parameters (Å, º) top
O2—C3 | 1.426 (3) | C10—C5 | 1.401 (2) |
O2—C1 | 1.436 (2) | C10—C4 | 1.510 (2) |
O80—C8 | 1.369 (2) | C41—C4 | 1.519 (2) |
O80—C80 | 1.420 (3) | C5—C6 | 1.375 (2) |
O45—C45 | 1.383 (3) | C5—H5 | 0.9300 |
O45—C450 | 1.416 (2) | C6—H6 | 0.9300 |
C42—O42 | 1.367 (2) | O42—C420 | 1.416 (3) |
C42—C43 | 1.387 (2) | C3—C4 | 1.529 (2) |
C42—C41 | 1.402 (3) | C3—H3 | 1.04 (2) |
C8—C7 | 1.377 (3) | C1—H11 | 0.9700 |
C8—C9 | 1.396 (2) | C1—H12 | 0.9700 |
C44—C45 | 1.375 (3) | C43—H43 | 0.9300 |
C44—C43 | 1.385 (3) | C4—H4 | 0.9800 |
C44—H44 | 0.9300 | C80—H801 | 0.9600 |
O3—C3 | 1.406 (2) | C80—H802 | 0.9600 |
O3—H30 | 0.99 (3) | C80—H803 | 0.9600 |
C9—C10 | 1.383 (3) | C420—H421 | 0.9600 |
C9—C1 | 1.497 (2) | C420—H422 | 0.9600 |
C7—C6 | 1.390 (3) | C420—H423 | 0.9600 |
C7—H7 | 0.9300 | C450—H451 | 0.9600 |
C46—C41 | 1.375 (3) | C450—H452 | 0.9600 |
C46—C45 | 1.403 (2) | C450—H453 | 0.9600 |
C46—H46 | 0.9300 | | |
| | | |
C3—O2—C1 | 113.8 (2) | O2—C3—H3 | 104 (1) |
C8—O80—C80 | 117.9 (2) | C4—C3—H3 | 111.3 (9) |
C45—O45—C450 | 118.2 (2) | C44—C45—O45 | 125.9 (2) |
O42—C42—C43 | 124.9 (2) | C44—C45—C46 | 119.6 (2) |
O42—C42—C41 | 115.0 (2) | O45—C45—C46 | 114.5 (2) |
C43—C42—C41 | 120.1 (2) | O2—C1—C9 | 113.3 (2) |
O80—C8—C7 | 123.9 (2) | O2—C1—H11 | 108.9 |
O80—C8—C9 | 114.7 (2) | C9—C1—H11 | 108.9 |
C7—C8—C9 | 121.4 (2) | O2—C1—H12 | 108.9 |
C45—C44—C43 | 119.7 (2) | C9—C1—H12 | 108.9 |
C45—C44—H44 | 120.1 | H11—C1—H12 | 107.7 |
C43—C44—H44 | 120.1 | C44—C43—C42 | 120.7 (2) |
C3—O3—H30 | 110 (2) | C44—C43—H43 | 119.7 |
C10—C9—C8 | 119.3 (2) | C42—C43—H43 | 119.7 |
C10—C9—C1 | 121.7 (2) | C10—C4—C41 | 113.0 (2) |
C8—C9—C1 | 119.0 (2) | C10—C4—C3 | 110.6 (2) |
C8—C7—C6 | 118.9 (2) | C41—C4—C3 | 110.5 (2) |
C8—C7—H7 | 120.6 | C10—C4—H4 | 107.5 |
C6—C7—H7 | 120.6 | C41—C4—H4 | 107.5 |
C41—C46—C45 | 121.3 (2) | C3—C4—H4 | 107.5 |
C41—C46—H46 | 119.3 | O80—C80—H801 | 109.5 |
C45—C46—H46 | 119.3 | O80—C80—H802 | 109.5 |
C9—C10—C5 | 119.4 (2) | H801—C80—H802 | 109.5 |
C9—C10—C4 | 119.9 (2) | O80—C80—H803 | 109.5 |
C5—C10—C4 | 120.6 (2) | H801—C80—H803 | 109.5 |
C46—C41—C42 | 118.5 (2) | H802—C80—H803 | 109.5 |
C46—C41—C4 | 122.7 (2) | O42—C420—H421 | 109.5 |
C42—C41—C4 | 118.8 (2) | O42—C420—H422 | 109.5 |
C6—C5—C10 | 120.3 (2) | H421—C420—H422 | 109.5 |
C6—C5—H5 | 119.8 | O42—C420—H423 | 109.5 |
C10—C5—H5 | 119.8 | H421—C420—H423 | 109.5 |
C5—C6—C7 | 120.6 (2) | H422—C420—H423 | 109.5 |
C5—C6—H6 | 119.7 | O45—C450—H451 | 109.5 |
C7—C6—H6 | 119.7 | O45—C450—H452 | 109.5 |
C42—O42—C420 | 118.8 (2) | H451—C450—H452 | 109.5 |
O3—C3—O2 | 110.7 (2) | O45—C450—H453 | 109.5 |
O3—C3—C4 | 110.0 (2) | H451—C450—H453 | 109.5 |
O2—C3—C4 | 109.8 (2) | H452—C450—H453 | 109.5 |
O3—C3—H3 | 111.3 (9) | | |
| | | |
C80—O80—C8—C7 | 22.8 (3) | C1—O2—C3—C4 | −64.8 (2) |
C80—O80—C8—C9 | −157.8 (2) | C43—C44—C45—O45 | −179.0 (2) |
O80—C8—C9—C10 | 178.7 (2) | C43—C44—C45—C46 | 1.5 (3) |
C7—C8—C9—C10 | −1.9 (3) | C450—O45—C45—C44 | −6.6 (3) |
O80—C8—C9—C1 | −2.7 (3) | C450—O45—C45—C46 | 172.8 (2) |
C7—C8—C9—C1 | 176.6 (2) | C41—C46—C45—C44 | 0.2 (3) |
O80—C8—C7—C6 | −179.5 (2) | C41—C46—C45—O45 | −179.3 (2) |
C9—C8—C7—C6 | 1.2 (3) | C3—O2—C1—C9 | 44.5 (3) |
C8—C9—C10—C5 | 0.8 (3) | C10—C9—C1—O2 | −13.5 (3) |
C1—C9—C10—C5 | −177.7 (2) | C8—C9—C1—O2 | 168.0 (2) |
C8—C9—C10—C4 | −177.3 (2) | C45—C44—C43—C42 | −1.0 (3) |
C1—C9—C10—C4 | 4.2 (3) | O42—C42—C43—C44 | −179.6 (2) |
C45—C46—C41—C42 | −2.3 (3) | C41—C42—C43—C44 | −1.2 (3) |
C45—C46—C41—C4 | 177.6 (2) | C9—C10—C4—C41 | 101.8 (2) |
O42—C42—C41—C46 | −178.6 (2) | C5—C10—C4—C41 | −76.2 (2) |
C43—C42—C41—C46 | 2.8 (3) | C9—C10—C4—C3 | −22.6 (2) |
O42—C42—C41—C4 | 1.5 (2) | C5—C10—C4—C3 | 159.3 (2) |
C43—C42—C41—C4 | −177.1 (2) | C46—C41—C4—C10 | −23.4 (2) |
C9—C10—C5—C6 | 1.0 (3) | C42—C41—C4—C10 | 156.5 (2) |
C4—C10—C5—C6 | 179.1 (2) | C46—C41—C4—C3 | 101.2 (2) |
C10—C5—C6—C7 | −1.8 (3) | C42—C41—C4—C3 | −79.0 (2) |
C8—C7—C6—C5 | 0.7 (3) | O3—C3—C4—C10 | −70.7 (2) |
C43—C42—O42—C420 | −5.3 (3) | O2—C3—C4—C10 | 51.4 (2) |
C41—C42—O42—C420 | 176.1 (2) | O3—C3—C4—C41 | 163.4 (2) |
C1—O2—C3—O3 | 56.9 (2) | O2—C3—C4—C41 | −74.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H30···O2i | 0.98 (4) | 1.90 (4) | 2.881 (2) | 171 (3) |
Symmetry code: (i) −x+5/2, −y, z+1/2. |