(3S,4R)-4-(2,5-Di­methoxy­phenyl)-8-methoxy­isochroman-3-ol

In the title compound, C₁₈H₂₀O₅, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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.

---

Computing details

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).

(3S,4R)-4-(2,5-Dimethoxyphenyl)-8-methoxyisochroman-3-ol

Crystal data

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) Å^3	Needle, colourless
Z = 4	0.50 × 0.28 × 0.18 mm

Data collection

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

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0726P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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+0.001xFc^2λ^3/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H30···O2^i	0.98 (4)	1.90 (4)	2.881 (2)	171 (3)

Symmetry code: (i) −x+5/2, −y, z+1/2.