8-Methoxy-4-(4-methoxyphenyl)isochroman-3-ol

In the title compound, C₁₇H₁₈O₄, the heterocyclic ring has a half-chair conformation. The substituents at the 3- and 4-positions are attached equatorially with respect to the heterocyclic ring. The mol­ecules are linked by O—H...O hydrogen bonds, the hydroxyl O atom functioning as both donor and acceptor. This results in the formation of C(2) chains running along the twofold screw axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.069
• wR factor = 0.185
• Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing ..          ?

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.19
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           67.49
           From the CIF: _reflns_number_total               1388
           Count of symmetry unique reflns         1430
           Completeness (_total/calc)             97.06%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PARST97 (Nardelli, 1996).

8-Methoxy-4-(4-methoxyphenyl)isochroman-3-ol

Crystal data

C17H18O4	F(000) = 304
Mr = 286.31	Dx = 1.342 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 45 reflections
a = 10.5330 (18) Å	θ = 45.6–57.4°
b = 5.145 (3) Å	µ = 0.78 mm^−1
c = 13.607 (3) Å	T = 293 K
β = 106.018 (15)°	Prism, colourless
V = 708.8 (5) Å^3	0.5 × 0.3 × 0.3 mm
Z = 2

Data collection

Rigaku AFC-5S diffractometer	Rint = 0.061
Graphite monochromator	θmax = 67.5°, θmin = 3.4°
ω scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = −6→6
Tmin = 0.750, Tmax = 0.793	l = −16→16
4913 measured reflections	3 standard reflections every 150 reflections
1388 independent reflections	intensity decay: <2%
1262 reflections with I > 2σ(I)

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.069	w = 1/[σ^2(Fo^2) + (0.153P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.185	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.53 e Å^−3
1388 reflections	Δρmin = −0.24 e Å^−3
193 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O2	0.1709 (2)	−0.0865 (6)	0.16822 (19)	0.0420 (7)
O31	−0.0210 (3)	−0.0785 (5)	0.04204 (19)	0.0431 (6)
H31	−0.0095	−0.2219	0.0196	0.065*
O8	0.3652 (2)	−0.0746 (7)	0.4743 (2)	0.0538 (8)
C3	0.0321 (3)	−0.0764 (8)	0.1480 (2)	0.0349 (8)
H3	0.0005	−0.2275	0.1783	0.042*
C4	−0.0086 (3)	0.1743 (8)	0.1915 (3)	0.0368 (8)
H4	0.0146	0.3199	0.1533	0.044*
C6	0.1064 (4)	0.4100 (10)	0.4671 (3)	0.0506 (10)
H6	0.0808	0.5311	0.5086	0.061*
C10	0.0719 (3)	0.2027 (7)	0.3033 (3)	0.0378 (8)
C9	0.1863 (3)	0.0577 (8)	0.3409 (3)	0.0410 (8)
O44	−0.5596 (3)	0.2056 (8)	0.1545 (3)	0.0630 (10)
C1	0.2349 (3)	−0.1223 (10)	0.2735 (3)	0.0471 (10)
H1A	0.3291	−0.0962	0.285	0.057*
H1B	0.2214	−0.3	0.2922	0.057*
C44	−0.4284 (4)	0.2087 (9)	0.1566 (3)	0.0456 (10)
C8	0.2574 (3)	0.0815 (9)	0.4439 (3)	0.0445 (9)
C5	0.0328 (4)	0.3799 (9)	0.3672 (3)	0.0458 (9)
H5	−0.0434	0.4781	0.342	0.055*
C80	0.4370 (5)	−0.0733 (14)	0.5805 (4)	0.0705 (15)
H80A	0.4782	0.0931	0.5982	0.106*
H80B	0.5036	−0.2062	0.5932	0.106*
H80C	0.3774	−0.106	0.6212	0.106*
C41	−0.1573 (3)	0.1843 (7)	0.1770 (3)	0.0374 (8)
C45	−0.3523 (4)	0.0236 (10)	0.2173 (3)	0.0491 (10)
H45	−0.3915	−0.0967	0.2508	0.059*
C46	−0.2172 (4)	0.0132 (10)	0.2295 (3)	0.0466 (10)
H46	−0.1662	−0.1096	0.2732	0.056*
C42	−0.2355 (4)	0.3688 (10)	0.1138 (3)	0.0475 (10)
H42	−0.1968	0.4837	0.0779	0.057*
C440	−0.6421 (4)	0.4063 (12)	0.1003 (4)	0.0643 (13)
H44A	−0.604	0.5721	0.124	0.096*
H44B	−0.7278	0.3932	0.1117	0.096*
H44C	−0.6503	0.3894	0.0285	0.096*
C43	−0.3715 (4)	0.3857 (9)	0.1029 (3)	0.0484 (10)
H43	−0.4228	0.5115	0.0611	0.058*
C7	0.2192 (4)	0.2600 (11)	0.5066 (3)	0.0526 (10)
H7	0.2685	0.2795	0.5743	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0341 (11)	0.0524 (17)	0.0417 (13)	0.0011 (12)	0.0144 (9)	−0.0032 (12)
O31	0.0476 (13)	0.0462 (15)	0.0341 (12)	0.0033 (13)	0.0091 (10)	−0.0031 (11)
O8	0.0424 (13)	0.069 (2)	0.0441 (15)	0.0065 (14)	0.0014 (11)	−0.0049 (14)
C3	0.0325 (15)	0.0373 (19)	0.0342 (16)	0.0038 (15)	0.0082 (12)	0.0000 (15)
C4	0.0348 (16)	0.041 (2)	0.0347 (16)	−0.0014 (15)	0.0091 (12)	0.0027 (15)
C6	0.056 (2)	0.050 (2)	0.047 (2)	0.005 (2)	0.0165 (17)	−0.0135 (19)
C10	0.0334 (15)	0.040 (2)	0.0398 (19)	−0.0037 (15)	0.0101 (14)	0.0000 (15)
C9	0.0354 (15)	0.045 (2)	0.0451 (19)	−0.0017 (15)	0.0147 (14)	−0.0005 (16)
O44	0.0343 (13)	0.079 (2)	0.078 (2)	0.0041 (16)	0.0183 (13)	0.0128 (19)
C1	0.0337 (16)	0.063 (3)	0.0428 (19)	0.0062 (18)	0.0078 (14)	−0.0046 (19)
C44	0.0343 (16)	0.051 (2)	0.052 (2)	0.0023 (17)	0.0129 (15)	−0.0011 (18)
C8	0.0334 (16)	0.052 (2)	0.047 (2)	−0.0006 (18)	0.0100 (14)	0.0003 (18)
C5	0.0440 (17)	0.049 (2)	0.046 (2)	0.0054 (18)	0.0160 (15)	−0.0009 (18)
C80	0.058 (2)	0.096 (4)	0.048 (2)	0.014 (3)	−0.001 (2)	0.001 (3)
C41	0.0350 (16)	0.040 (2)	0.0362 (16)	0.0027 (16)	0.0091 (13)	−0.0012 (15)
C45	0.0425 (19)	0.057 (3)	0.052 (2)	−0.0013 (18)	0.0193 (17)	0.0074 (19)
C46	0.0383 (17)	0.054 (2)	0.049 (2)	0.0053 (17)	0.0147 (15)	0.0079 (18)
C42	0.0373 (16)	0.058 (3)	0.0465 (19)	−0.0033 (18)	0.0107 (14)	0.0107 (19)
C440	0.0359 (17)	0.072 (3)	0.083 (3)	0.010 (2)	0.0124 (19)	0.004 (3)
C43	0.0368 (17)	0.051 (2)	0.052 (2)	0.0057 (17)	0.0045 (15)	0.0107 (19)
C7	0.051 (2)	0.065 (3)	0.0384 (19)	−0.001 (2)	0.0078 (16)	−0.0112 (19)

Geometric parameters (Å, º)

O2—C3	1.413 (4)	C1—H1B	0.97
O2—C1	1.417 (4)	C44—C45	1.366 (6)
O31—C3	1.396 (4)	C44—C43	1.402 (6)
O31—H31	0.82	C8—C7	1.386 (6)
O8—C8	1.359 (5)	C5—H5	0.93
O8—C80	1.435 (5)	C80—H80A	0.96
C3—C4	1.528 (5)	C80—H80B	0.96
C3—H3	0.98	C80—H80C	0.96
C4—C41	1.525 (4)	C41—C42	1.389 (6)
C4—C10	1.531 (5)	C41—C46	1.389 (6)
C4—H4	0.98	C45—C46	1.388 (5)
C6—C5	1.376 (5)	C45—H45	0.93
C6—C7	1.394 (6)	C46—H46	0.93
C6—H6	0.93	C42—C43	1.402 (5)
C10—C9	1.389 (5)	C42—H42	0.93
C10—C5	1.398 (5)	C440—H44A	0.96
C9—C8	1.400 (5)	C440—H44B	0.96
C9—C1	1.489 (6)	C440—H44C	0.96
O44—C44	1.374 (4)	C43—H43	0.93
O44—C440	1.418 (6)	C7—H7	0.93
C1—H1A	0.97
C3—O2—C1	112.3 (2)	O8—C8—C9	115.0 (3)
C3—O31—H31	109.5	C7—C8—C9	120.6 (4)
C8—O8—C80	117.9 (3)	C6—C5—C10	120.4 (4)
O31—C3—O2	107.4 (3)	C6—C5—H5	119.8
O31—C3—C4	109.3 (3)	C10—C5—H5	119.8
O2—C3—C4	109.9 (3)	O8—C80—H80A	109.5
O31—C3—H3	110	O8—C80—H80B	109.5
O2—C3—H3	110	H80A—C80—H80B	109.5
C4—C3—H3	110	O8—C80—H80C	109.5
C41—C4—C3	111.5 (3)	H80A—C80—H80C	109.5
C41—C4—C10	113.1 (3)	H80B—C80—H80C	109.5
C3—C4—C10	109.1 (3)	C42—C41—C46	118.4 (3)
C41—C4—H4	107.6	C42—C41—C4	121.0 (3)
C3—C4—H4	107.6	C46—C41—C4	120.5 (3)
C10—C4—H4	107.6	C44—C45—C46	120.7 (4)
C5—C6—C7	120.4 (4)	C44—C45—H45	119.7
C5—C6—H6	119.8	C46—C45—H45	119.7
C7—C6—H6	119.8	C45—C46—C41	120.7 (4)
C9—C10—C5	119.7 (3)	C45—C46—H46	119.7
C9—C10—C4	120.1 (3)	C41—C46—H46	119.7
C5—C10—C4	120.2 (3)	C41—C42—C43	121.4 (4)
C10—C9—C8	119.4 (3)	C41—C42—H42	119.3
C10—C9—C1	121.2 (3)	C43—C42—H42	119.3
C8—C9—C1	119.4 (3)	O44—C440—H44A	109.5
C44—O44—C440	118.1 (4)	O44—C440—H44B	109.5
O2—C1—C9	113.2 (3)	H44A—C440—H44B	109.5
O2—C1—H1A	108.9	O44—C440—H44C	109.5
C9—C1—H1A	108.9	H44A—C440—H44C	109.5
O2—C1—H1B	108.9	H44B—C440—H44C	109.5
C9—C1—H1B	108.9	C42—C43—C44	118.4 (4)
H1A—C1—H1B	107.8	C42—C43—H43	120.8
C45—C44—O44	115.1 (4)	C44—C43—H43	120.8
C45—C44—C43	120.3 (3)	C8—C7—C6	119.4 (4)
O44—C44—C43	124.6 (4)	C8—C7—H7	120.3
O8—C8—C7	124.4 (4)	C6—C7—H7	120.3
C1—O2—C3—O31	−171.7 (3)	C10—C9—C8—C7	−4.1 (6)
C1—O2—C3—C4	69.5 (4)	C1—C9—C8—C7	175.7 (4)
O31—C3—C4—C41	65.9 (4)	C7—C6—C5—C10	−1.5 (7)
O2—C3—C4—C41	−176.4 (3)	C9—C10—C5—C6	−0.4 (6)
O31—C3—C4—C10	−168.4 (3)	C4—C10—C5—C6	−178.7 (4)
O2—C3—C4—C10	−50.8 (4)	C3—C4—C41—C42	−114.4 (4)
C41—C4—C10—C9	141.7 (4)	C10—C4—C41—C42	122.2 (4)
C3—C4—C10—C9	17.0 (4)	C3—C4—C41—C46	67.5 (4)
C41—C4—C10—C5	−40.1 (5)	C10—C4—C41—C46	−55.9 (5)
C3—C4—C10—C5	−164.8 (3)	O44—C44—C45—C46	−177.2 (4)
C5—C10—C9—C8	3.2 (5)	C43—C44—C45—C46	2.2 (7)
C4—C10—C9—C8	−178.6 (3)	C44—C45—C46—C41	−2.6 (7)
C5—C10—C9—C1	−176.6 (4)	C42—C41—C46—C45	1.2 (6)
C4—C10—C9—C1	1.6 (6)	C4—C41—C46—C45	179.3 (4)
C3—O2—C1—C9	−48.4 (4)	C46—C41—C42—C43	0.5 (6)
C10—C9—C1—O2	12.6 (5)	C4—C41—C42—C43	−177.6 (4)
C8—C9—C1—O2	−167.3 (3)	C41—C42—C43—C44	−0.9 (7)
C440—O44—C44—C45	174.6 (4)	C45—C44—C43—C42	−0.5 (6)
C440—O44—C44—C43	−4.8 (6)	O44—C44—C43—C42	178.9 (4)
C80—O8—C8—C7	6.4 (6)	O8—C8—C7—C6	−180.0 (5)
C80—O8—C8—C9	−175.7 (4)	C9—C8—C7—C6	2.2 (7)
C10—C9—C8—O8	177.9 (4)	C5—C6—C7—C8	0.6 (7)
C1—C9—C8—O8	−2.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O31—H31···O31^i	0.82	2.08	2.899 (4)	178

Symmetry code: (i) −x, y−1/2, −z.