Futoenone, a neolignan from Magnolia soulangiana

Song, Q.; Billodeaux, D.R.; Fronczek, F.R.; Fischer, N.H.

doi:10.1107/S1600536801017482

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Futoenone, a neolignan from Magnolia soulangiana

Q. Song, D. R. Billodeaux, F. R. Fronczek and N. H. Fischer

In the title compound, (2R,4R,5S,5aR)-rel-(-)-4-(1,3-benzodioxol-5-yl)-2,3,4,5-tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-benzoepin-8-one, C₂₀H₂₀O₅, the tetrahydrofuran ring has an envelope conformation, and the semiquinone ring is somewhat non-planar, with deviations from coplanarity of up to 0.1603 (13) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017482/ob6082sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017482/ob6082Isup2.hkl Contains datablock I

CCDC reference: 176030

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.003 Å
R factor = 0.033
wR factor = 0.085
Data-to-parameter ratio = 7.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           74.90
         From the CIF: _reflns_number_total               1748
         Count of symmetry unique reflns         1704
         Completeness (_total/calc)            102.58%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured        44
         Fraction of Friedel pairs measured     0.026
         Are heavy atom types Z>Si present           no
          WARNING: CuKa measured Friedel data can be used to
                   determine absolute structure in a light-atom
                   study only if the Friedel fraction is large.

Comment top

The title neolignan, (I), has been previously reported from Piper futokadsura (Ogiso et al., 1968), Magnolia denudata (Iida et al., 1982), Magnolia liliflora (Iida & Ito, 1983; Talapatra et al., 1982) and other plants (Shizuri & Yamamura, 1983). The crystal structure of an orthorhombic (P2₁2₁2₁) polymorph has been previously reported (Roychowdhury & Gosh, 1984), but its coordinates are not available. The conformation of the molecule in the orthorhombic polymorph is reported by Roychowdhury & Gosh to be somewhat different from what we find, even in the portion of the molecule with three fused rings, which might be expected to be rather rigid. They report the tetrahydrofuran ring to be a half chair, while in the present trigonal polymorph, it is clearly envelope, with C7' lying 0.689 (3) Å out of the best plane of the other four atoms. Further, they report that all atoms of the semiquinone ring `except (the spiro C atom) lie on a plane since the torsion angles associated with this group are within 6° of zero'. We find larger deviations, with torsion angles about C3'—C4' and C4'—C5' differing from zero by 12.7 (3) and 19.8 (3)°, respectively. In the present structure, the six atoms of the semiquinone ring deviate from coplanarity by distances ranging from -0.0310 (14) Å for C3' to 0.1603 (13) Å for C1'. We find the C8—C1' bond to be somewhat elongated at 1.583 (2) Å, which was also noted by Roychowdhury & Gosh (1.589 Å).

In the title structure, a short intermolecular C4'···O2(y-x, 1 - x, z - 1/3) contact exists with a distance of 2.968 (3) Å.

Experimental top

Leaves of Magnolia soulangiana, collected in Vancouver, BC, Canada, were air-dried, ground, and extracted with CH₂Cl₂ at room temperature for 24 h. The crude extract was separated by standard vacuum liquid chromatography procedures (Cantrell et al., 1996), using silica gel and n-hexane/ethyl acetate mixtures of increasing polarity. Fractions 58–61 (of 66) yielded crystals of futoenone.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: maXus (Mackay et al., 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The atom-numbering scheme for (I) with ellipsoids at the 40% probability level.

(2R,4R,5S,5aR)-rel-(-)-4-(1,3-benzodioxol-5-yl)-2,3,4,5- tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-benzoepin-8-one top

Crystal data top

C₂₀H₂₀O₅	D_x = 1.369 Mg m⁻³
M_r = 340.36	Cu Kα radiation, λ = 1.54180 Å
Trigonal, P3₁	Cell parameters from 25 reflections
a = 7.5210 (6) Å	θ = 23.5–42.6°
c = 25.2821 (13) Å	µ = 0.81 mm⁻¹
V = 1238.50 (15) Å³	T = 297 K
Z = 3	Trigonal prism, colorless
F(000) = 540	0.45 × 0.34 × 0.34 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	1727 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 74.9°, θ_min = 5.2°
θ/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.614, T_max = 0.724	l = 0→31
4948 measured reflections	3 standard reflections every 120 min
1748 independent reflections	intensity decay: 1.0%

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0526P)² + 0.0948P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
1748 reflections	Δρ_max = 0.23 e Å⁻³
229 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (11)

Crystal data top

C₂₀H₂₀O₅	Z = 3
M_r = 340.36	Cu Kα radiation
Trigonal, P3₁	µ = 0.81 mm⁻¹
a = 7.5210 (6) Å	T = 297 K
c = 25.2821 (13) Å	0.45 × 0.34 × 0.34 mm
V = 1238.50 (15) Å³

Data collection top

Enraf-Nonius CAD-4 diffractometer	1727 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.614, T_max = 0.724	3 standard reflections every 120 min
4948 measured reflections	intensity decay: 1.0%
1748 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.085	H-atom parameters constrained
S = 1.10	Δρ_max = 0.23 e Å⁻³
1748 reflections	Δρ_min = −0.17 e Å⁻³
229 parameters

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	U_iso*/U_eq
O1	1.1479 (2)	0.8471 (3)	0.50004 (7)	0.0556 (4)
O2	1.0624 (3)	0.7416 (3)	0.58724 (7)	0.0585 (5)
O3	0.0405 (2)	0.3643 (3)	0.39544 (6)	0.0447 (4)
O4	−0.0828 (3)	−0.2487 (3)	0.31202 (9)	0.0627 (5)
O5	0.1715 (3)	−0.0237 (3)	0.23485 (7)	0.0586 (5)
C1	0.5913 (3)	0.5173 (3)	0.47896 (7)	0.0339 (4)
C2	0.7965 (3)	0.6495 (3)	0.46484 (7)	0.0360 (4)
H2	0.8337	0.6903	0.4299	0.043*
C3	0.9402 (3)	0.7163 (3)	0.50433 (8)	0.0371 (4)
C4	0.8881 (3)	0.6548 (3)	0.55644 (8)	0.0406 (4)
C5	0.6907 (4)	0.5273 (4)	0.57151 (8)	0.0443 (5)
H5	0.6562	0.4872	0.6066	0.053*
C6	0.5414 (3)	0.4591 (3)	0.53158 (8)	0.0405 (4)
H6	0.4046	0.3722	0.5405	0.049*
C7	0.4204 (3)	0.4515 (3)	0.43851 (7)	0.0332 (4)
H7	0.3009	0.3293	0.4530	0.040*
C8	0.4647 (3)	0.3891 (3)	0.38414 (7)	0.0317 (4)
H8	0.5975	0.5008	0.3719	0.038*
C9	0.4833 (4)	0.1974 (4)	0.38983 (9)	0.0458 (5)
H9A	0.5852	0.2209	0.4160	0.069*
H9B	0.5231	0.1665	0.3565	0.069*
H9C	0.3534	0.0840	0.4005	0.069*
C10	1.2275 (4)	0.8593 (5)	0.55230 (11)	0.0607 (7)
H10A	1.3222	0.8071	0.5522	0.073*
H10B	1.3013	1.0012	0.5639	0.073*
C11	0.2894 (4)	0.1053 (5)	0.19187 (10)	0.0603 (7)
H11A	0.2513	0.2079	0.1858	0.090*
H11B	0.2631	0.0237	0.1605	0.090*
H11C	0.4328	0.1708	0.2004	0.090*
C1'	0.2961 (3)	0.3639 (3)	0.34259 (7)	0.0322 (4)
C2'	0.0864 (3)	0.2419 (3)	0.36637 (7)	0.0359 (4)
C3'	−0.0398 (3)	0.0420 (3)	0.35842 (9)	0.0444 (5)
H3'	−0.1583	−0.0298	0.3786	0.053*
C4'	0.0103 (3)	−0.0621 (3)	0.31786 (9)	0.0439 (5)
C5'	0.1776 (3)	0.0751 (3)	0.28038 (8)	0.0404 (4)
C6'	0.3121 (3)	0.2697 (3)	0.29222 (7)	0.0369 (4)
H6'	0.4177	0.3481	0.2687	0.044*
C7'	0.3057 (3)	0.5726 (3)	0.33730 (8)	0.0401 (4)
H7'1	0.4457	0.6850	0.3339	0.048*
H7'2	0.2245	0.5745	0.3078	0.048*
C8'	0.2118 (3)	0.5766 (4)	0.39009 (9)	0.0425 (5)
H8'	0.1629	0.6754	0.3899	0.051*
C9'	0.3607 (4)	0.6189 (4)	0.43475 (8)	0.0425 (5)
H9'1	0.2987	0.6253	0.4678	0.051*
H9'2	0.4832	0.7511	0.4292	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0400 (7)	0.0791 (11)	0.0386 (9)	0.0229 (8)	−0.0077 (7)	−0.0096 (8)
O2	0.0596 (10)	0.0853 (12)	0.0309 (9)	0.0364 (9)	−0.0199 (7)	−0.0184 (8)
O3	0.0414 (7)	0.0673 (9)	0.0283 (7)	0.0294 (7)	0.0021 (6)	0.0008 (7)
O4	0.0682 (11)	0.0391 (8)	0.0628 (12)	0.0132 (7)	−0.0149 (9)	0.0062 (7)
O5	0.0782 (11)	0.0523 (9)	0.0327 (9)	0.0231 (9)	−0.0089 (8)	−0.0164 (7)
C1	0.0410 (9)	0.0439 (9)	0.0172 (8)	0.0215 (8)	−0.0002 (7)	−0.0029 (7)
C2	0.0413 (9)	0.0500 (10)	0.0160 (8)	0.0224 (8)	−0.0003 (7)	−0.0008 (7)
C3	0.0394 (9)	0.0480 (10)	0.0258 (10)	0.0234 (8)	−0.0024 (7)	−0.0072 (8)
C4	0.0532 (11)	0.0560 (11)	0.0214 (9)	0.0338 (9)	−0.0119 (8)	−0.0141 (8)
C5	0.0612 (12)	0.0594 (12)	0.0148 (9)	0.0320 (10)	−0.0023 (8)	−0.0037 (8)
C6	0.0448 (10)	0.0524 (11)	0.0186 (9)	0.0200 (8)	0.0023 (7)	−0.0027 (8)
C7	0.0362 (8)	0.0471 (9)	0.0162 (8)	0.0208 (7)	0.0005 (6)	−0.0026 (7)
C8	0.0335 (8)	0.0417 (9)	0.0164 (8)	0.0162 (7)	−0.0003 (6)	−0.0039 (7)
C9	0.0547 (11)	0.0564 (12)	0.0353 (12)	0.0346 (10)	−0.0098 (9)	−0.0097 (9)
C10	0.0530 (13)	0.0927 (19)	0.0395 (14)	0.0388 (13)	−0.0171 (11)	−0.0310 (13)
C11	0.0661 (15)	0.0802 (17)	0.0251 (11)	0.0295 (13)	−0.0038 (10)	−0.0183 (11)
C1'	0.0365 (8)	0.0386 (8)	0.0151 (8)	0.0140 (7)	−0.0001 (7)	0.0003 (6)
C2'	0.0367 (9)	0.0518 (10)	0.0176 (8)	0.0209 (8)	−0.0013 (7)	0.0045 (7)
C3'	0.0373 (9)	0.0525 (11)	0.0301 (10)	0.0126 (8)	−0.0008 (8)	0.0133 (8)
C4'	0.0447 (10)	0.0405 (9)	0.0348 (11)	0.0124 (8)	−0.0133 (8)	0.0052 (8)
C5'	0.0517 (10)	0.0432 (9)	0.0217 (9)	0.0203 (8)	−0.0079 (8)	−0.0040 (8)
C6'	0.0443 (9)	0.0428 (9)	0.0151 (8)	0.0154 (8)	0.0013 (7)	−0.0004 (7)
C7'	0.0508 (10)	0.0433 (10)	0.0222 (10)	0.0205 (8)	−0.0025 (8)	0.0027 (7)
C8'	0.0510 (10)	0.0538 (11)	0.0316 (11)	0.0329 (9)	−0.0030 (8)	−0.0022 (8)
C9'	0.0536 (11)	0.0582 (11)	0.0241 (10)	0.0341 (10)	−0.0044 (8)	−0.0105 (8)

Geometric parameters (Å, º) top

O1—C3	1.372 (3)	C9—H9A	0.9600
O1—C10	1.435 (3)	C9—H9B	0.9600
O2—C4	1.377 (3)	C9—H9C	0.9600
O2—C10	1.416 (4)	C10—H10A	0.9700
O3—C2'	1.351 (3)	C10—H10B	0.9700
O3—C8'	1.473 (3)	C11—H11A	0.9600
O4—C4'	1.224 (3)	C11—H11B	0.9600
O5—C5'	1.358 (3)	C11—H11C	0.9600
O5—C11	1.431 (3)	C1'—C6'	1.491 (2)
C1—C6	1.392 (3)	C1'—C2'	1.498 (2)
C1—C2	1.401 (3)	C1'—C7'	1.541 (3)
C1—C7	1.519 (2)	C2'—C3'	1.332 (3)
C2—C3	1.369 (3)	C3'—C4'	1.450 (3)
C2—H2	0.9300	C3'—H3'	0.9300
C3—C4	1.386 (3)	C4'—C5'	1.499 (3)
C4—C5	1.359 (3)	C5'—C6'	1.332 (3)
C5—C6	1.402 (3)	C6'—H6'	0.9300
C5—H5	0.9300	C7'—C8'	1.517 (3)
C6—H6	0.9300	C7'—H7'1	0.9700
C7—C9'	1.537 (3)	C7'—H7'2	0.9700
C7—C8	1.542 (2)	C8'—C9'	1.508 (3)
C7—H7	0.9800	C8'—H8'	0.9800
C8—C9	1.523 (3)	C9'—H9'1	0.9700
C8—C1'	1.583 (2)	C9'—H9'2	0.9700
C8—H8	0.9800

C3—O1—C10	105.20 (19)	O5—C11—H11A	109.5
C4—O2—C10	105.84 (19)	O5—C11—H11B	109.5
C2'—O3—C8'	107.78 (15)	H11A—C11—H11B	109.5
C5'—O5—C11	115.64 (19)	O5—C11—H11C	109.5
C6—C1—C2	119.65 (18)	H11A—C11—H11C	109.5
C6—C1—C7	119.34 (17)	H11B—C11—H11C	109.5
C2—C1—C7	120.80 (17)	C6'—C1'—C2'	111.24 (15)
C3—C2—C1	117.53 (17)	C6'—C1'—C7'	115.85 (16)
C3—C2—H2	121.2	C2'—C1'—C7'	99.03 (15)
C1—C2—H2	121.2	C6'—C1'—C8	111.95 (15)
C2—C3—O1	127.76 (19)	C2'—C1'—C8	110.03 (14)
C2—C3—C4	122.06 (18)	C7'—C1'—C8	107.97 (15)
O1—C3—C4	110.18 (18)	C3'—C2'—O3	124.81 (19)
C5—C4—O2	128.4 (2)	C3'—C2'—C1'	124.61 (19)
C5—C4—C3	121.93 (18)	O3—C2'—C1'	110.54 (17)
O2—C4—C3	109.6 (2)	C2'—C3'—C4'	119.05 (19)
C4—C5—C6	116.67 (18)	C2'—C3'—H3'	120.5
C4—C5—H5	121.7	C4'—C3'—H3'	120.5
C6—C5—H5	121.7	O4—C4'—C3'	123.4 (2)
C1—C6—C5	122.16 (19)	O4—C4'—C5'	121.0 (2)
C1—C6—H6	118.9	C3'—C4'—C5'	115.52 (18)
C5—C6—H6	118.9	C6'—C5'—O5	126.2 (2)
C1—C7—C9'	108.71 (15)	C6'—C5'—C4'	121.93 (19)
C1—C7—C8	115.04 (15)	O5—C5'—C4'	111.84 (18)
C9'—C7—C8	112.98 (15)	C5'—C6'—C1'	121.12 (18)
C1—C7—H7	106.5	C5'—C6'—H6'	119.4
C9'—C7—H7	106.5	C1'—C6'—H6'	119.4
C8—C7—H7	106.5	C8'—C7'—C1'	99.15 (16)
C9—C8—C7	109.86 (16)	C8'—C7'—H7'1	111.9
C9—C8—C1'	113.33 (15)	C1'—C7'—H7'1	111.9
C7—C8—C1'	110.25 (14)	C8'—C7'—H7'2	111.9
C9—C8—H8	107.7	C1'—C7'—H7'2	111.9
C7—C8—H8	107.7	H7'1—C7'—H7'2	109.6
C1'—C8—H8	107.7	O3—C8'—C9'	108.35 (18)
C8—C9—H9A	109.5	O3—C8'—C7'	102.87 (17)
C8—C9—H9B	109.5	C9'—C8'—C7'	111.03 (17)
H9A—C9—H9B	109.5	O3—C8'—H8'	111.4
C8—C9—H9C	109.5	C9'—C8'—H8'	111.4
H9A—C9—H9C	109.5	C7'—C8'—H8'	111.4
H9B—C9—H9C	109.5	C8'—C9'—C7	111.32 (16)
O2—C10—O1	109.09 (19)	C8'—C9'—H9'1	109.4
O2—C10—H10A	109.9	C7—C9'—H9'1	109.4
O1—C10—H10A	109.9	C8'—C9'—H9'2	109.4
O2—C10—H10B	109.9	C7—C9'—H9'2	109.4
O1—C10—H10B	109.9	H9'1—C9'—H9'2	108.0
H10A—C10—H10B	108.3

C6—C1—C2—C3	−0.1 (3)	C8'—O3—C2'—C1'	3.3 (2)
C7—C1—C2—C3	174.48 (18)	C6'—C1'—C2'—C3'	26.0 (3)
C1—C2—C3—O1	−179.1 (2)	C7'—C1'—C2'—C3'	148.33 (19)
C1—C2—C3—C4	0.9 (3)	C8—C1'—C2'—C3'	−98.7 (2)
C10—O1—C3—C2	−177.6 (2)	C6'—C1'—C2'—O3	−151.92 (16)
C10—O1—C3—C4	2.3 (2)	C7'—C1'—C2'—O3	−29.55 (19)
C10—O2—C4—C5	179.4 (2)	C8—C1'—C2'—O3	83.43 (18)
C10—O2—C4—C3	−0.5 (2)	O3—C2'—C3'—C4'	167.15 (18)
C2—C3—C4—C5	−1.2 (3)	C1'—C2'—C3'—C4'	−10.4 (3)
O1—C3—C4—C5	178.9 (2)	C2'—C3'—C4'—O4	171.1 (2)
C2—C3—C4—O2	178.76 (19)	C2'—C3'—C4'—C5'	−12.7 (3)
O1—C3—C4—O2	−1.2 (2)	C11—O5—C5'—C6'	−15.0 (3)
O2—C4—C5—C6	−179.4 (2)	C11—O5—C5'—C4'	164.9 (2)
C3—C4—C5—C6	0.5 (3)	O4—C4'—C5'—C6'	−163.9 (2)
C2—C1—C6—C5	−0.5 (3)	C3'—C4'—C5'—C6'	19.8 (3)
C7—C1—C6—C5	−175.19 (19)	O4—C4'—C5'—O5	16.2 (3)
C4—C5—C6—C1	0.3 (3)	C3'—C4'—C5'—O5	−160.10 (18)
C6—C1—C7—C9'	91.1 (2)	O5—C5'—C6'—C1'	176.8 (2)
C2—C1—C7—C9'	−83.5 (2)	C4'—C5'—C6'—C1'	−3.1 (3)
C6—C1—C7—C8	−141.08 (18)	C2'—C1'—C6'—C5'	−18.2 (3)
C2—C1—C7—C8	44.3 (2)	C7'—C1'—C6'—C5'	−130.2 (2)
C1—C7—C8—C9	64.9 (2)	C8—C1'—C6'—C5'	105.4 (2)
C9'—C7—C8—C9	−169.50 (17)	C6'—C1'—C7'—C8'	161.05 (16)
C1—C7—C8—C1'	−169.55 (15)	C2'—C1'—C7'—C8'	42.06 (18)
C9'—C7—C8—C1'	−43.9 (2)	C8—C1'—C7'—C8'	−72.52 (17)
C4—O2—C10—O1	2.0 (3)	C2'—O3—C8'—C9'	−92.49 (18)
C3—O1—C10—O2	−2.6 (3)	C2'—O3—C8'—C7'	25.1 (2)
C9—C8—C1'—C6'	−46.7 (2)	C1'—C7'—C8'—O3	−41.81 (18)
C7—C8—C1'—C6'	−170.28 (15)	C1'—C7'—C8'—C9'	73.9 (2)
C9—C8—C1'—C2'	77.6 (2)	O3—C8'—C9'—C7	51.3 (2)
C7—C8—C1'—C2'	−46.0 (2)	C7'—C8'—C9'—C7	−60.9 (2)
C9—C8—C1'—C7'	−175.35 (17)	C1—C7—C9'—C8'	172.37 (18)
C7—C8—C1'—C7'	61.04 (19)	C8—C7—C9'—C8'	43.4 (2)
C8'—O3—C2'—C3'	−174.57 (18)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀O₅
M_r	340.36
Crystal system, space group	Trigonal, P3₁
Temperature (K)	297
a, c (Å)	7.5210 (6), 25.2821 (13)
V (Å³)	1238.50 (15)
Z	3
Radiation type	Cu Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.45 × 0.34 × 0.34

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.614, 0.724
No. of measured, independent and observed [I > 2σ(I)] reflections	4948, 1748, 1727
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.085, 1.10
No. of reflections	1748
No. of parameters	229
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, maXus (Mackay et al., 1999), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

O1—C10	1.435 (3)	O3—C8'	1.473 (3)
O2—C10	1.416 (4)	O4—C4'	1.224 (3)
O3—C2'	1.351 (3)	C8—C1'	1.583 (2)

C3—O1—C10	105.20 (19)	C2'—O3—C8'	107.78 (15)
C4—O2—C10	105.84 (19)

C2—C1—C7—C8	44.3 (2)	C3'—C4'—C5'—C6'	19.8 (3)
C8'—O3—C2'—C1'	3.3 (2)	C4'—C5'—C6'—C1'	−3.1 (3)
C6'—C1'—C2'—C3'	26.0 (3)	C2'—C1'—C6'—C5'	−18.2 (3)
C7'—C1'—C2'—O3	−29.55 (19)	C2'—C1'—C7'—C8'	42.06 (18)
C1'—C2'—C3'—C4'	−10.4 (3)	C2'—O3—C8'—C7'	25.1 (2)
C2'—C3'—C4'—C5'	−12.7 (3)	C1'—C7'—C8'—O3	−41.81 (18)

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