Methyl [5-methoxy-4-(3-methoxy­phenyl)­isochroman-3-yl]­acetate

In the title compound, C₂₀H₂₂O₅, the heterocyclic ring has a half-boat conformation. The methoxy­carbonyl­methyl substituent is in an equatorial position. The substituents in positions 3 and 4 are in a trans configuration.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.055
• wR factor = 0.157
• Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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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).

Methyl [5-methoxy-4-(3-methoxyphenyl)isochroman-3-yl]acetate

Crystal data

C20H22O5	Z = 2
Mr = 342.38	F(000) = 364
Triclinic, P1	Dx = 1.294 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.057 (1) Å	Cell parameters from 25 reflections
b = 11.145 (2) Å	θ = 22.9–28.4°
c = 11.408 (1) Å	µ = 0.76 mm^−1
α = 68.918 (7)°	T = 295 K
β = 71.859 (8)°	Cut block, colourless
γ = 70.345 (9)°	0.32 × 0.25 × 0.15 mm
V = 878.8 (2) Å^3

Data collection

Rigaku AFC-5S diffractometer	1732 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
Graphite monochromator	θmax = 72.5°, θmin = 4.3°
ω scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −13→11
Tmin = 0.793, Tmax = 0.895	l = −14→13
3500 measured reflections	3 standard reflections every 150 reflections
3319 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0865P)^2] where P = (Fo^2 + 2Fc^2)/3'
S = 0.87	(Δ/σ)max < 0.001
3319 reflections	Δρmax = 0.20 e Å^−3
242 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0128 (15)

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	0.8727 (3)	0.38598 (17)	0.00825 (17)	0.0591 (6)
O5	0.7461 (3)	0.01085 (17)	0.36544 (18)	0.0663 (6)
O310	0.7510 (3)	0.44030 (19)	−0.25979 (18)	0.0672 (6)
O43	0.3914 (3)	−0.12455 (18)	0.18987 (19)	0.0647 (6)
C41	0.5671 (3)	0.1590 (2)	0.1476 (2)	0.0424 (6)
C44	0.2419 (4)	0.0965 (3)	0.1828 (3)	0.0593 (8)
O311	1.0473 (3)	0.3538 (2)	−0.3083 (2)	0.0918 (8)
C4	0.7408 (4)	0.1939 (2)	0.1305 (2)	0.0445 (6)
H4	0.8398	0.1145	0.1239	0.053*
C9	0.7545 (3)	0.3561 (2)	0.2356 (3)	0.0474 (7)
C43	0.4053 (4)	0.0006 (3)	0.1751 (2)	0.0499 (7)
C3	0.7741 (4)	0.3046 (2)	0.0034 (2)	0.0473 (7)
H3	0.6566	0.3611	−0.0145	0.057*
C10	0.7423 (3)	0.2301 (2)	0.2452 (2)	0.0455 (6)
C1	0.7777 (4)	0.4535 (2)	0.1038 (2)	0.0540 (7)
H11	0.6602	0.5061	0.0863	0.065*
H12	0.8439	0.5133	0.1007	0.065*
C46	0.4031 (4)	0.2541 (3)	0.1577 (2)	0.0514 (7)
H46	0.4007	0.3397	0.1529	0.062*
C30	0.8760 (4)	0.2479 (2)	−0.1078 (2)	0.0557 (7)
H31	0.9931	0.1924	−0.0914	0.067*
H32	0.8108	0.1915	−0.1130	0.067*
C42	0.5652 (4)	0.0316 (2)	0.1561 (2)	0.0484 (7)
H42	0.6733	−0.0334	0.1489	0.058*
C31	0.9035 (4)	0.3513 (3)	−0.2350 (3)	0.0585 (8)
C45	0.2445 (4)	0.2229 (3)	0.1746 (3)	0.0604 (8)
H45	0.1364	0.2881	0.1807	0.072*
C310	0.7651 (5)	0.5457 (3)	−0.3797 (3)	0.0773 (10)
H311	0.8276	0.5077	−0.4497	0.116*
H312	0.8306	0.6020	−0.3766	0.116*
H313	0.6463	0.5973	−0.3920	0.116*
C5	0.7423 (4)	0.1339 (3)	0.3666 (3)	0.0544 (7)
C430	0.5535 (4)	−0.2287 (3)	0.1891 (3)	0.0785 (10)
H431	0.6090	−0.2365	0.2556	0.118*
H432	0.6349	−0.2088	0.1071	0.118*
H433	0.5257	−0.3110	0.2041	0.118*
C8	0.7496 (4)	0.3877 (3)	0.3435 (3)	0.0620 (8)
C6	0.7341 (5)	0.1662 (3)	0.4733 (3)	0.0706 (9)
C50	0.7511 (5)	−0.0938 (3)	0.4825 (3)	0.0832 (11)
H51	0.6492	−0.0690	0.5479	0.125*
H52	0.8605	−0.1097	0.5089	0.125*
H53	0.7470	−0.1731	0.4695	0.125*
C7	0.7386 (5)	0.2939 (3)	0.4617 (3)	0.0739 (10)
H7	0.7341	0.3158	0.5341	0.089*
H8	0.771 (4)	0.468 (3)	0.340 (3)	0.078 (10)*
H44	0.129 (4)	0.072 (3)	0.202 (3)	0.081 (10)*
H6	0.736 (4)	0.103 (3)	0.551 (3)	0.083 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0768 (14)	0.0513 (11)	0.0502 (11)	−0.0308 (10)	−0.0038 (10)	−0.0104 (9)
O5	0.0978 (17)	0.0461 (11)	0.0527 (12)	−0.0296 (11)	−0.0254 (11)	0.0068 (9)
O310	0.0727 (15)	0.0605 (12)	0.0496 (12)	−0.0191 (11)	−0.0051 (10)	0.0009 (9)
O43	0.0726 (15)	0.0550 (12)	0.0774 (14)	−0.0292 (11)	−0.0154 (11)	−0.0199 (10)
C41	0.0502 (17)	0.0396 (13)	0.0376 (13)	−0.0151 (12)	−0.0095 (11)	−0.0078 (11)
C44	0.055 (2)	0.0631 (19)	0.0609 (19)	−0.0222 (16)	−0.0135 (15)	−0.0115 (14)
O311	0.0801 (17)	0.0972 (18)	0.0654 (15)	−0.0249 (14)	0.0092 (12)	−0.0048 (13)
C4	0.0492 (16)	0.0368 (13)	0.0420 (14)	−0.0129 (11)	−0.0054 (11)	−0.0069 (11)
C9	0.0454 (16)	0.0468 (15)	0.0512 (16)	−0.0154 (12)	−0.0087 (12)	−0.0133 (12)
C43	0.0582 (19)	0.0501 (16)	0.0479 (15)	−0.0252 (14)	−0.0103 (13)	−0.0119 (12)
C3	0.0579 (18)	0.0446 (14)	0.0388 (14)	−0.0206 (13)	−0.0094 (12)	−0.0050 (11)
C10	0.0487 (17)	0.0426 (14)	0.0411 (14)	−0.0129 (12)	−0.0097 (12)	−0.0061 (11)
C1	0.068 (2)	0.0431 (15)	0.0502 (16)	−0.0181 (13)	−0.0088 (14)	−0.0120 (13)
C46	0.0548 (19)	0.0439 (15)	0.0502 (16)	−0.0129 (13)	−0.0095 (13)	−0.0084 (12)
C30	0.0638 (19)	0.0501 (16)	0.0467 (16)	−0.0200 (14)	−0.0044 (13)	−0.0078 (13)
C42	0.0536 (17)	0.0423 (14)	0.0473 (15)	−0.0127 (12)	−0.0082 (12)	−0.0123 (12)
C31	0.069 (2)	0.0569 (17)	0.0448 (16)	−0.0212 (16)	−0.0022 (15)	−0.0130 (14)
C45	0.0537 (19)	0.0565 (18)	0.0597 (19)	−0.0079 (14)	−0.0108 (14)	−0.0107 (14)
C310	0.100 (3)	0.066 (2)	0.0468 (18)	−0.0256 (18)	−0.0106 (17)	0.0049 (15)
C5	0.068 (2)	0.0482 (16)	0.0478 (16)	−0.0241 (14)	−0.0146 (14)	−0.0045 (13)
C430	0.083 (3)	0.0528 (18)	0.101 (3)	−0.0215 (18)	−0.010 (2)	−0.0279 (18)
C8	0.077 (2)	0.0609 (19)	0.0562 (19)	−0.0293 (17)	−0.0078 (16)	−0.0206 (16)
C6	0.096 (3)	0.072 (2)	0.0439 (17)	−0.0342 (19)	−0.0171 (17)	−0.0028 (16)
C50	0.118 (3)	0.0564 (19)	0.066 (2)	−0.029 (2)	−0.039 (2)	0.0155 (16)
C7	0.100 (3)	0.080 (2)	0.056 (2)	−0.035 (2)	−0.0169 (18)	−0.0237 (17)

Geometric parameters (Å, º)

O2—C3	1.416 (3)	C1—H11	0.9700
O2—C1	1.422 (3)	C1—H12	0.9700
O5—C5	1.366 (3)	C46—C45	1.374 (4)
O5—C50	1.423 (3)	C46—H46	0.9300
O310—C31	1.329 (3)	C30—C31	1.500 (4)
O310—C310	1.449 (3)	C30—H31	0.9700
O43—C43	1.382 (3)	C30—H32	0.9700
O43—C430	1.426 (3)	C42—H42	0.9300
C41—C46	1.390 (3)	C45—H45	0.9300
C41—C42	1.393 (3)	C310—H311	0.9600
C41—C4	1.513 (3)	C310—H312	0.9600
C44—C45	1.384 (4)	C310—H313	0.9600
C44—C43	1.390 (4)	C5—C6	1.366 (4)
C44—H44	0.97 (3)	C430—H431	0.9600
O311—C31	1.202 (3)	C430—H432	0.9600
C4—C10	1.506 (3)	C430—H433	0.9600
C4—C3	1.546 (3)	C8—C7	1.376 (4)
C4—H4	0.9800	C8—H8	0.95 (3)
C9—C8	1.383 (4)	C6—C7	1.393 (4)
C9—C10	1.403 (3)	C6—H6	0.92 (3)
C9—C1	1.504 (3)	C50—H51	0.9600
C43—C42	1.378 (4)	C50—H52	0.9600
C3—C30	1.504 (3)	C50—H53	0.9600
C3—H3	0.9800	C7—H7	0.9300
C10—C5	1.414 (3)
C3—O2—C1	111.2 (2)	C31—C30—H32	108.8
C5—O5—C50	118.0 (2)	C3—C30—H32	108.8
C31—O310—C310	116.9 (2)	H31—C30—H32	107.7
C43—O43—C430	117.3 (2)	C43—C42—C41	120.9 (3)
C46—C41—C42	118.0 (2)	C43—C42—H42	119.5
C46—C41—C4	120.4 (2)	C41—C42—H42	119.5
C42—C41—C4	121.6 (2)	O311—C31—O310	122.9 (3)
C45—C44—C43	117.9 (3)	O311—C31—C30	124.1 (3)
C45—C44—H44	121.9 (18)	O310—C31—C30	113.0 (3)
C43—C44—H44	119.8 (18)	C46—C45—C44	121.5 (3)
C10—C4—C41	111.5 (2)	C46—C45—H45	119.2
C10—C4—C3	112.2 (2)	C44—C45—H45	119.2
C41—C4—C3	110.4 (2)	O310—C310—H311	109.5
C10—C4—H4	107.5	O310—C310—H312	109.5
C41—C4—H4	107.5	H311—C310—H312	109.5
C3—C4—H4	107.5	O310—C310—H313	109.5
C8—C9—C10	120.9 (2)	H311—C310—H313	109.5
C8—C9—C1	121.5 (2)	H312—C310—H313	109.5
C10—C9—C1	117.6 (2)	C6—C5—O5	124.9 (2)
C42—C43—O43	124.4 (3)	C6—C5—C10	121.4 (3)
C42—C43—C44	120.9 (3)	O5—C5—C10	113.7 (2)
O43—C43—C44	114.7 (2)	O43—C430—H431	109.5
O2—C3—C30	107.4 (2)	O43—C430—H432	109.5
O2—C3—C4	113.1 (2)	H431—C430—H432	109.5
C30—C3—C4	111.5 (2)	O43—C430—H433	109.5
O2—C3—H3	108.2	H431—C430—H433	109.5
C30—C3—H3	108.2	H432—C430—H433	109.5
C4—C3—H3	108.2	C7—C8—C9	120.1 (3)
C9—C10—C5	117.2 (2)	C7—C8—H8	115.5 (18)
C9—C10—C4	122.3 (2)	C9—C8—H8	123.8 (18)
C5—C10—C4	120.4 (2)	C5—C6—C7	119.7 (3)
O2—C1—C9	110.7 (2)	C5—C6—H6	120.7 (19)
O2—C1—H11	109.5	C7—C6—H6	119.3 (19)
C9—C1—H11	109.5	O5—C50—H51	109.5
O2—C1—H12	109.5	O5—C50—H52	109.5
C9—C1—H12	109.5	H51—C50—H52	109.5
H11—C1—H12	108.1	O5—C50—H53	109.5
C45—C46—C41	120.7 (3)	H51—C50—H53	109.5
C45—C46—H46	119.6	H52—C50—H53	109.5
C41—C46—H46	119.6	C8—C7—C6	120.3 (3)
C31—C30—C3	113.8 (2)	C8—C7—H7	119.8
C31—C30—H31	108.8	C6—C7—H7	119.8
C3—C30—H31	108.8
C46—C41—C4—C10	63.5 (3)	C4—C41—C46—C45	−179.3 (2)
C42—C41—C4—C10	−115.3 (3)	O2—C3—C30—C31	−58.6 (3)
C46—C41—C4—C3	−62.0 (3)	C4—C3—C30—C31	176.9 (2)
C42—C41—C4—C3	119.2 (2)	O43—C43—C42—C41	−177.2 (2)
C430—O43—C43—C42	2.0 (4)	C44—C43—C42—C41	1.8 (4)
C430—O43—C43—C44	−177.1 (3)	C46—C41—C42—C43	−0.6 (4)
C45—C44—C43—C42	−1.9 (4)	C4—C41—C42—C43	178.2 (2)
C45—C44—C43—O43	177.2 (2)	C310—O310—C31—O311	−1.9 (4)
C1—O2—C3—C30	174.8 (2)	C310—O310—C31—C30	178.8 (2)
C1—O2—C3—C4	−61.7 (3)	C3—C30—C31—O311	128.5 (3)
C10—C4—C3—O2	25.7 (3)	C3—C30—C31—O310	−52.2 (4)
C41—C4—C3—O2	150.7 (2)	C41—C46—C45—C44	0.3 (4)
C10—C4—C3—C30	146.9 (2)	C43—C44—C45—C46	0.8 (4)
C41—C4—C3—C30	−88.1 (3)	C50—O5—C5—C6	−3.3 (4)
C8—C9—C10—C5	−5.8 (4)	C50—O5—C5—C10	178.4 (3)
C1—C9—C10—C5	172.6 (2)	C9—C10—C5—C6	7.1 (4)
C8—C9—C10—C4	177.9 (2)	C4—C10—C5—C6	−176.5 (3)
C1—C9—C10—C4	−3.7 (4)	C9—C10—C5—O5	−174.6 (2)
C41—C4—C10—C9	−118.4 (3)	C4—C10—C5—O5	1.8 (4)
C3—C4—C10—C9	6.0 (3)	C10—C9—C8—C7	2.1 (5)
C41—C4—C10—C5	65.4 (3)	C1—C9—C8—C7	−176.2 (3)
C3—C4—C10—C5	−170.2 (2)	O5—C5—C6—C7	177.3 (3)
C3—O2—C1—C9	63.3 (3)	C10—C5—C6—C7	−4.6 (5)
C8—C9—C1—O2	148.5 (3)	C9—C8—C7—C6	0.6 (5)
C10—C9—C1—O2	−30.0 (3)	C5—C6—C7—C8	0.6 (5)
C42—C41—C46—C45	−0.4 (4)