Hydrogen-bonded aggregations of oxo-cholic acids

Bertolasi, V.; Ferretti, V.; Pretto, L.; Fantin, G.; Fogagnolo, M.; Bortolini, O.

doi:10.1107/S0108768105011304

Hydrogen-bonded aggregations of oxo-cholic acids

V. Bertolasi, V. Ferretti, L. Pretto, G. Fantin, M. Fogagnolo and O. Bortolini

The crystal structures of six new crystals of oxo-cholic acids (oxo-CA) are reported: (I) 3α,12α-dihydroxy-7-oxo-5β-cholan-24-oic acid; (II) 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid; (III) 7α-hydroxy-3,12-dioxo-5β-cholan-24-oic acid; (IV-α) and (IV-β) 12α-hydroxy-3,7-dioxo-5β-cholan-24-oic acid; (V) 3,7,12-trihydroxy-5β-cholan-24-oic acid. (IV-β) is a pseudopolymorphic solvated form of (IV-α) and contains small channels which can trap disordered water molecules. In all the structures the four saturated cycles, forming the common alicyclic skeleton, have the same conformation, while the carboxylic side chain adopts flexible conformations in order to produce the most efficient crystal aggregations. The structures display a variety of supramolecular architectures dominated by networks of cooperative O—H

O hydrogen bonds forming different packing motifs often supported by weaker C—H

O interactions.

Keywords: hydrogen bonding; aggregation; polymorphism.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105011304/sn5016sup1.cif Contains datablocks (I), (II), (III), (IV-alpha), (IV-beta), (V)
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105011304/sn5016Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105011304/sn5016IIsup3.hkl Contains datablock (II)
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105011304/sn5016IIIsup4.hkl Contains datablock (III)
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105011304/sn5016IV-alphasup5.hkl Contains datablock (IV-alpha)
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105011304/sn5016IV-betasup6.hkl Contains datablock (IV-beta)
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105011304/sn5016Vsup7.hkl Contains datablock V

CCDC references: 274186; 274187; 274188; 274189; 274190; 274191

Computing details top

For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO SMN (Otwinowski & Minor, 1997); data reduction: DENZO SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 1999).

Figures top

(I) top

Crystal data top

C₂₄H₃₈O₅	D_x = 1.209 Mg m⁻³
M_r = 406.54	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3690 reflections
a = 8.9879 (1) Å	θ = 3.8–28.0°
b = 9.4028 (1) Å	µ = 0.08 mm⁻¹
c = 26.4369 (4) Å	T = 295 K
V = 2234.22 (5) Å³	Prism, colourless
Z = 4	0.42 × 0.35 × 0.28 mm
F(000) = 888

Data collection top

Nonius Kappa CCD diffractometer	2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 28.0°, θ_min = 3.8°
ϕ scans and ω scans	h = −11→11
24241 measured reflections	k = −12→12
3049 independent reflections	l = −34→34

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0534P)² + 0.2792P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3049 reflections	Δρ_max = 0.15 e Å⁻³
277 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −3.4 (15)

Crystal data top

C₂₄H₃₈O₅	V = 2234.22 (5) Å³
M_r = 406.54	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.9879 (1) Å	µ = 0.08 mm⁻¹
b = 9.4028 (1) Å	T = 295 K
c = 26.4369 (4) Å	0.42 × 0.35 × 0.28 mm

Data collection top

Nonius Kappa CCD diffractometer	2385 reflections with I > 2σ(I)
24241 measured reflections	R_int = 0.041
3049 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	Δρ_max = 0.15 e Å⁻³
S = 1.04	Δρ_min = −0.13 e Å⁻³
3049 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
277 parameters	Absolute structure parameter: −3.4 (15)
0 restraints

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
C1	0.2899 (2)	0.5704 (3)	0.09002 (9)	0.0640 (6)
H1A	0.2150	0.5468	0.0650	0.077*
H1B	0.2452	0.5584	0.1231	0.077*
C2	0.3334 (3)	0.7254 (3)	0.08348 (9)	0.0635 (6)
H2A	0.2455	0.7847	0.0864	0.076*
H2B	0.4021	0.7525	0.1101	0.076*
C3	0.4056 (3)	0.7500 (3)	0.03250 (9)	0.0619 (6)
H3	0.3304	0.7382	0.0060	0.074*
C4	0.5320 (3)	0.6470 (3)	0.02285 (8)	0.0557 (5)
H4A	0.6147	0.6714	0.0448	0.067*
H4B	0.5652	0.6579	−0.0118	0.067*
C5	0.4901 (3)	0.4906 (3)	0.03182 (8)	0.0557 (5)
H5	0.4160	0.4638	0.0064	0.067*
C6	0.6293 (3)	0.3977 (3)	0.02333 (8)	0.0646 (6)
H6A	0.6018	0.2979	0.0235	0.078*
H6B	0.6734	0.4196	−0.0092	0.078*
C7	0.7391 (2)	0.4263 (3)	0.06457 (8)	0.0534 (5)
C8	0.6836 (2)	0.3990 (2)	0.11761 (7)	0.0466 (5)
H8	0.6553	0.2986	0.1203	0.056*
C9	0.5422 (2)	0.4919 (2)	0.12564 (7)	0.0462 (4)
H9	0.5742	0.5908	0.1213	0.055*
C10	0.4205 (2)	0.4654 (3)	0.08484 (8)	0.0537 (5)
C11	0.4853 (2)	0.4798 (3)	0.18057 (8)	0.0556 (5)
H11A	0.4042	0.5466	0.1852	0.067*
H11B	0.4458	0.3848	0.1857	0.067*
C12	0.6040 (2)	0.5085 (3)	0.22078 (7)	0.0506 (5)
H12	0.5603	0.4839	0.2536	0.061*
C13	0.7394 (2)	0.4101 (2)	0.21293 (7)	0.0431 (4)
C14	0.7974 (2)	0.4317 (2)	0.15823 (7)	0.0432 (4)
H14	0.8224	0.5327	0.1549	0.052*
C15	0.9443 (2)	0.3500 (3)	0.15770 (8)	0.0541 (5)
H15A	1.0127	0.3903	0.1332	0.065*
H15B	0.9281	0.2506	0.1496	0.065*
C16	1.0046 (2)	0.3667 (3)	0.21165 (8)	0.0561 (6)
H16A	1.0959	0.4218	0.2114	0.067*
H16B	1.0254	0.2743	0.2263	0.067*
C17	0.8834 (2)	0.4445 (2)	0.24272 (7)	0.0453 (4)
H17	0.9015	0.5466	0.2386	0.054*
C18	0.6910 (3)	0.2566 (2)	0.22346 (9)	0.0561 (5)
H18A	0.6332	0.2536	0.2540	0.067*
H18B	0.7774	0.1976	0.2273	0.067*
H18C	0.6320	0.2224	0.1957	0.067*
C19	0.3559 (3)	0.3147 (3)	0.08837 (11)	0.0785 (8)
H19A	0.3017	0.3048	0.1195	0.094*
H19B	0.4355	0.2466	0.0876	0.094*
H19C	0.2903	0.2983	0.0603	0.094*
C20	0.8902 (2)	0.4133 (2)	0.30027 (7)	0.0511 (5)
H20	0.8593	0.3146	0.3059	0.061*
C21	0.7847 (3)	0.5109 (3)	0.32949 (8)	0.0681 (7)
H21A	0.8041	0.5026	0.3651	0.082*
H21B	0.6837	0.4838	0.3227	0.082*
H21C	0.8001	0.6075	0.3190	0.082*
C22	1.0507 (3)	0.4298 (3)	0.31846 (8)	0.0572 (5)
H22A	1.1121	0.3619	0.3003	0.069*
H22B	1.0850	0.5242	0.3093	0.069*
C23	1.0761 (3)	0.4089 (3)	0.37480 (9)	0.0696 (7)
H23A	1.0311	0.4874	0.3930	0.083*
H23B	1.0273	0.3220	0.3855	0.083*
C24	1.2379 (3)	0.4007 (3)	0.38822 (9)	0.0608 (6)
O25	0.4613 (2)	0.8939 (2)	0.03084 (8)	0.0791 (6)
O26	0.6460 (2)	0.65463 (19)	0.22323 (6)	0.0626 (4)
O27	1.3292 (3)	0.3376 (3)	0.36384 (8)	0.1006 (8)
O28	1.2734 (3)	0.4657 (2)	0.43049 (7)	0.0815 (6)
O29	0.86061 (18)	0.4784 (2)	0.05647 (6)	0.0717 (5)
H25	0.431 (4)	0.935 (4)	0.0040 (14)	0.103 (11)*
H26	0.652 (4)	0.692 (4)	0.1941 (12)	0.110 (12)*
H28	1.377 (5)	0.442 (4)	0.4406 (15)	0.134 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0351 (10)	0.0919 (18)	0.0650 (13)	−0.0003 (12)	−0.0031 (10)	−0.0075 (13)
C2	0.0438 (11)	0.0825 (17)	0.0643 (13)	0.0168 (12)	−0.0106 (10)	−0.0090 (12)
C3	0.0528 (13)	0.0708 (14)	0.0622 (12)	0.0065 (12)	−0.0167 (11)	−0.0002 (12)
C4	0.0456 (11)	0.0733 (15)	0.0481 (10)	0.0024 (11)	−0.0045 (9)	0.0019 (10)
C5	0.0472 (11)	0.0693 (14)	0.0505 (11)	0.0010 (11)	−0.0062 (9)	−0.0103 (11)
C6	0.0687 (15)	0.0749 (16)	0.0504 (11)	0.0133 (14)	0.0034 (11)	−0.0120 (11)
C7	0.0492 (12)	0.0620 (13)	0.0490 (10)	0.0151 (11)	0.0101 (9)	0.0013 (10)
C8	0.0418 (10)	0.0491 (11)	0.0490 (10)	0.0018 (9)	0.0092 (8)	0.0012 (9)
C9	0.0358 (9)	0.0537 (11)	0.0491 (10)	0.0004 (9)	0.0044 (8)	−0.0007 (9)
C10	0.0402 (10)	0.0639 (13)	0.0570 (11)	−0.0063 (10)	−0.0025 (9)	−0.0056 (10)
C11	0.0364 (10)	0.0762 (15)	0.0541 (11)	0.0066 (11)	0.0101 (8)	0.0001 (11)
C12	0.0408 (10)	0.0655 (13)	0.0454 (10)	0.0053 (10)	0.0090 (8)	0.0018 (10)
C13	0.0366 (9)	0.0474 (10)	0.0451 (9)	0.0012 (9)	0.0095 (8)	0.0059 (9)
C14	0.0375 (9)	0.0456 (10)	0.0466 (9)	0.0026 (9)	0.0092 (8)	0.0047 (8)
C15	0.0404 (10)	0.0689 (14)	0.0530 (11)	0.0108 (11)	0.0111 (9)	0.0071 (10)
C16	0.0422 (10)	0.0688 (14)	0.0572 (12)	0.0096 (11)	0.0056 (9)	0.0086 (11)
C17	0.0403 (9)	0.0471 (10)	0.0485 (9)	0.0001 (9)	0.0052 (8)	0.0086 (9)
C18	0.0526 (12)	0.0552 (12)	0.0604 (12)	−0.0064 (11)	0.0100 (10)	0.0099 (11)
C19	0.0684 (17)	0.0791 (18)	0.0878 (17)	−0.0240 (15)	−0.0042 (15)	−0.0072 (16)
C20	0.0514 (11)	0.0540 (12)	0.0478 (10)	0.0020 (11)	0.0026 (9)	0.0100 (10)
C21	0.0646 (14)	0.0885 (18)	0.0512 (11)	0.0107 (16)	0.0079 (11)	0.0044 (12)
C22	0.0560 (12)	0.0637 (14)	0.0518 (11)	0.0009 (12)	−0.0017 (10)	0.0085 (11)
C23	0.0683 (15)	0.0861 (18)	0.0543 (12)	0.0019 (15)	−0.0045 (11)	0.0075 (13)
C24	0.0686 (15)	0.0620 (14)	0.0517 (11)	0.0078 (13)	−0.0061 (11)	−0.0020 (11)
O25	0.0903 (14)	0.0728 (12)	0.0742 (11)	0.0061 (11)	−0.0358 (11)	0.0123 (10)
O26	0.0715 (11)	0.0568 (9)	0.0594 (9)	0.0161 (8)	−0.0006 (9)	−0.0038 (8)
O27	0.0858 (14)	0.1320 (18)	0.0840 (12)	0.0418 (15)	−0.0294 (12)	−0.0405 (14)
O28	0.0836 (13)	0.0997 (15)	0.0613 (10)	0.0119 (12)	−0.0127 (10)	−0.0198 (10)
O29	0.0493 (9)	0.1111 (15)	0.0549 (8)	0.0082 (10)	0.0129 (7)	0.0217 (9)

Geometric parameters (Å, º) top

C1—C2	1.519 (4)	C13—C17	1.549 (3)
C1—C10	1.540 (3)	C13—C14	1.551 (2)
C1—H1A	0.9700	C14—C15	1.528 (3)
C1—H1B	0.9700	C14—H14	0.9800
C2—C3	1.514 (3)	C15—C16	1.534 (3)
C2—H2A	0.9700	C15—H15A	0.9700
C2—H2B	0.9700	C15—H15B	0.9700
C3—O25	1.443 (3)	C16—C17	1.548 (3)
C3—C4	1.514 (3)	C16—H16A	0.9700
C3—H3	0.9800	C16—H16B	0.9700
C4—C5	1.536 (3)	C17—C20	1.551 (3)
C4—H4A	0.9700	C17—H17	0.9800
C4—H4B	0.9700	C18—H18A	0.9600
C5—C6	1.542 (3)	C18—H18B	0.9600
C5—C10	1.553 (3)	C18—H18C	0.9600
C5—H5	0.9800	C19—H19A	0.9600
C6—C7	1.495 (3)	C19—H19B	0.9600
C6—H6A	0.9700	C19—H19C	0.9600
C6—H6B	0.9700	C20—C22	1.529 (3)
C7—O29	1.216 (3)	C20—C21	1.529 (3)
C7—C8	1.510 (3)	C20—H20	0.9800
C8—C14	1.515 (3)	C21—H21A	0.9600
C8—C9	1.557 (3)	C21—H21B	0.9600
C8—H8	0.9800	C21—H21C	0.9600
C9—C11	1.544 (3)	C22—C23	1.519 (3)
C9—C10	1.556 (3)	C22—H22A	0.9700
C9—H9	0.9800	C22—H22B	0.9700
C10—C19	1.535 (4)	C23—C24	1.498 (4)
C11—C12	1.530 (3)	C23—H23A	0.9700
C11—H11A	0.9700	C23—H23B	0.9700
C11—H11B	0.9700	C24—O27	1.200 (3)
C12—O26	1.426 (3)	C24—O28	1.313 (3)
C12—C13	1.543 (3)	O25—H25	0.85 (4)
C12—H12	0.9800	O26—H26	0.85 (3)
C13—C18	1.533 (3)	O28—H28	1.00 (4)

C2—C1—C10	114.14 (19)	C12—C13—C17	117.75 (17)
C2—C1—H1A	108.7	C18—C13—C14	112.83 (17)
C10—C1—H1A	108.7	C12—C13—C14	108.20 (16)
C2—C1—H1B	108.7	C17—C13—C14	99.54 (14)
C10—C1—H1B	108.7	C8—C14—C15	118.35 (17)
H1A—C1—H1B	107.6	C8—C14—C13	114.05 (15)
C3—C2—C1	111.0 (2)	C15—C14—C13	103.50 (15)
C3—C2—H2A	109.4	C8—C14—H14	106.7
C1—C2—H2A	109.4	C15—C14—H14	106.7
C3—C2—H2B	109.4	C13—C14—H14	106.7
C1—C2—H2B	109.4	C14—C15—C16	104.20 (17)
H2A—C2—H2B	108.0	C14—C15—H15A	110.9
O25—C3—C2	108.6 (2)	C16—C15—H15A	110.9
O25—C3—C4	109.5 (2)	C14—C15—H15B	110.9
C2—C3—C4	112.0 (2)	C16—C15—H15B	110.9
O25—C3—H3	108.9	H15A—C15—H15B	108.9
C2—C3—H3	108.9	C15—C16—C17	107.04 (17)
C4—C3—H3	108.9	C15—C16—H16A	110.3
C3—C4—C5	113.76 (19)	C17—C16—H16A	110.3
C3—C4—H4A	108.8	C15—C16—H16B	110.3
C5—C4—H4A	108.8	C17—C16—H16B	110.3
C3—C4—H4B	108.8	H16A—C16—H16B	108.6
C5—C4—H4B	108.8	C16—C17—C13	102.71 (16)
H4A—C4—H4B	107.7	C16—C17—C20	113.80 (17)
C4—C5—C6	108.7 (2)	C13—C17—C20	119.50 (16)
C4—C5—C10	112.55 (18)	C16—C17—H17	106.7
C6—C5—C10	111.83 (19)	C13—C17—H17	106.7
C4—C5—H5	107.8	C20—C17—H17	106.7
C6—C5—H5	107.8	C13—C18—H18A	109.5
C10—C5—H5	107.8	C13—C18—H18B	109.5
C7—C6—C5	109.09 (17)	H18A—C18—H18B	109.5
C7—C6—H6A	109.9	C13—C18—H18C	109.5
C5—C6—H6A	109.9	H18A—C18—H18C	109.5
C7—C6—H6B	109.9	H18B—C18—H18C	109.5
C5—C6—H6B	109.9	C10—C19—H19A	109.5
H6A—C6—H6B	108.3	C10—C19—H19B	109.5
O29—C7—C6	122.5 (2)	H19A—C19—H19B	109.5
O29—C7—C8	121.9 (2)	C10—C19—H19C	109.5
C6—C7—C8	115.39 (19)	H19A—C19—H19C	109.5
C7—C8—C14	113.63 (16)	H19B—C19—H19C	109.5
C7—C8—C9	107.49 (16)	C22—C20—C21	111.4 (2)
C14—C8—C9	109.91 (16)	C22—C20—C17	109.08 (17)
C7—C8—H8	108.6	C21—C20—C17	110.97 (18)
C14—C8—H8	108.6	C22—C20—H20	108.4
C9—C8—H8	108.6	C21—C20—H20	108.4
C11—C9—C10	114.04 (16)	C17—C20—H20	108.4
C11—C9—C8	110.94 (17)	C20—C21—H21A	109.5
C10—C9—C8	112.92 (16)	C20—C21—H21B	109.5
C11—C9—H9	106.1	H21A—C21—H21B	109.5
C10—C9—H9	106.1	C20—C21—H21C	109.5
C8—C9—H9	106.1	H21A—C21—H21C	109.5
C19—C10—C1	107.37 (19)	H21B—C21—H21C	109.5
C19—C10—C5	110.4 (2)	C23—C22—C20	115.9 (2)
C1—C10—C5	106.85 (19)	C23—C22—H22A	108.3
C19—C10—C9	111.8 (2)	C20—C22—H22A	108.3
C1—C10—C9	111.81 (18)	C23—C22—H22B	108.3
C5—C10—C9	108.55 (17)	C20—C22—H22B	108.3
C12—C11—C9	114.17 (16)	H22A—C22—H22B	107.4
C12—C11—H11A	108.7	C24—C23—C22	112.6 (2)
C9—C11—H11A	108.7	C24—C23—H23A	109.1
C12—C11—H11B	108.7	C22—C23—H23A	109.1
C9—C11—H11B	108.7	C24—C23—H23B	109.1
H11A—C11—H11B	107.6	C22—C23—H23B	109.1
O26—C12—C11	112.74 (19)	H23A—C23—H23B	107.8
O26—C12—C13	112.02 (17)	O27—C24—O28	121.4 (2)
C11—C12—C13	110.52 (17)	O27—C24—C23	124.2 (2)
O26—C12—H12	107.1	O28—C24—C23	114.4 (2)
C11—C12—H12	107.1	C3—O25—H25	110 (2)
C13—C12—H12	107.1	C12—O26—H26	112 (2)
C18—C13—C12	108.45 (16)	C24—O28—H28	111 (2)
C18—C13—C17	109.94 (17)

(II) top

Crystal data top

C₂₄H₃₈O₅	D_x = 1.225 Mg m⁻³
M_r = 406.54	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2878 reflections
a = 6.3122 (1) Å	θ = 3.7–28.0°
b = 10.8884 (2) Å	µ = 0.08 mm⁻¹
c = 32.0624 (7) Å	T = 295 K
V = 2203.64 (7) Å³	Prism, colourless
Z = 4	0.36 × 0.14 × 0.10 mm
F(000) = 888

Data collection top

Nonius Kappa CCD diffractometer	2415 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.076
Graphite monochromator	θ_max = 28.0°, θ_min = 3.7°
ϕ scans and ω scans	h = −8→8
13705 measured reflections	k = −14→14
3006 independent reflections	l = −41→42

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0556P)² + 0.316P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3006 reflections	Δρ_max = 0.16 e Å⁻³
277 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.2 (15)

Crystal data top

C₂₄H₃₈O₅	V = 2203.64 (7) Å³
M_r = 406.54	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.3122 (1) Å	µ = 0.08 mm⁻¹
b = 10.8884 (2) Å	T = 295 K
c = 32.0624 (7) Å	0.36 × 0.14 × 0.10 mm

Data collection top

Nonius Kappa CCD diffractometer	2415 reflections with I > 2σ(I)
13705 measured reflections	R_int = 0.076
3006 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	Δρ_max = 0.16 e Å⁻³
S = 1.04	Δρ_min = −0.16 e Å⁻³
3006 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
277 parameters	Absolute structure parameter: 1.2 (15)
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6355 (5)	1.2414 (2)	0.30325 (8)	0.0532 (6)
H1A	0.5160	1.2620	0.2856	0.064*
H1B	0.6470	1.3048	0.3244	0.064*
C2	0.8364 (5)	1.2430 (2)	0.27674 (8)	0.0509 (6)
H2A	0.8495	1.3219	0.2629	0.061*
H2B	0.9593	1.2318	0.2945	0.061*
C3	0.8280 (4)	1.1414 (2)	0.24449 (7)	0.0459 (5)
H3	0.7114	1.1581	0.2251	0.055*
C4	0.7928 (4)	1.0181 (2)	0.26448 (7)	0.0457 (5)
H4A	0.9148	0.9979	0.2815	0.055*
H4B	0.7812	0.9563	0.2428	0.055*
C5	0.5930 (4)	1.0144 (2)	0.29169 (7)	0.0489 (6)
H5A	0.4723	1.0289	0.2731	0.059*
C6	0.5608 (5)	0.8869 (3)	0.31102 (8)	0.0566 (7)
H6A	0.4154	0.8804	0.3206	0.068*
H6B	0.5813	0.8255	0.2895	0.068*
C7	0.7072 (4)	0.8572 (2)	0.34730 (7)	0.0485 (6)
H7	0.6565	0.7819	0.3607	0.058*
C8	0.7078 (4)	0.9600 (2)	0.37976 (7)	0.0401 (5)
H8	0.5655	0.9643	0.3919	0.048*
C9	0.7553 (4)	1.0860 (2)	0.35923 (7)	0.0374 (5)
H9	0.8905	1.0762	0.3446	0.045*
C10	0.5886 (4)	1.1177 (2)	0.32515 (7)	0.0458 (6)
C11	0.7898 (4)	1.1899 (2)	0.39118 (7)	0.0457 (5)
H11A	0.8616	1.2573	0.3774	0.055*
H11B	0.6525	1.2196	0.4003	0.055*
C12	0.9175 (4)	1.1533 (2)	0.42950 (7)	0.0417 (5)
C13	0.8506 (3)	1.0350 (2)	0.45024 (6)	0.0368 (5)
C14	0.8629 (4)	0.9380 (2)	0.41498 (6)	0.0378 (5)
H14	1.0052	0.9441	0.4029	0.045*
C15	0.8549 (5)	0.8172 (2)	0.43895 (7)	0.0490 (6)
H15A	0.9088	0.7500	0.4222	0.059*
H15B	0.7114	0.7982	0.4476	0.059*
C16	0.9976 (5)	0.8409 (2)	0.47664 (8)	0.0539 (7)
H16A	1.1379	0.8074	0.4718	0.065*
H16B	0.9388	0.8024	0.5014	0.065*
C17	1.0095 (4)	0.9831 (2)	0.48253 (7)	0.0392 (5)
H17	1.1502	1.0073	0.4725	0.047*
C18	0.6251 (4)	1.0511 (3)	0.46784 (7)	0.0496 (6)
H18A	0.5336	1.0823	0.4464	0.060*
H18B	0.6284	1.1078	0.4907	0.060*
H18C	0.5728	0.9732	0.4773	0.060*
C19	0.3648 (4)	1.1276 (3)	0.34388 (9)	0.0680 (8)
H19A	0.2645	1.1435	0.3220	0.082*
H19B	0.3612	1.1936	0.3637	0.082*
H19C	0.3292	1.0520	0.3576	0.082*
C20	0.9966 (3)	1.0296 (2)	0.52814 (7)	0.0392 (5)
H20	0.9455	1.1145	0.5276	0.047*
C21	1.2203 (4)	1.0298 (3)	0.54682 (8)	0.0529 (6)
H21A	1.3038	1.0923	0.5336	0.064*
H21B	1.2852	0.9511	0.5424	0.064*
H21C	1.2120	1.0460	0.5762	0.064*
C22	0.8495 (4)	0.9551 (2)	0.55686 (6)	0.0419 (5)
H22A	0.7213	0.9346	0.5417	0.050*
H22B	0.9192	0.8789	0.5644	0.050*
C23	0.7903 (4)	1.0241 (2)	0.59641 (7)	0.0484 (6)
H23A	0.9181	1.0568	0.6090	0.058*
H23B	0.7003	1.0930	0.5891	0.058*
C24	0.6776 (4)	0.9465 (2)	0.62792 (7)	0.0475 (6)
O25	1.0238 (3)	1.13399 (19)	0.22117 (5)	0.0537 (5)
O26	1.0688 (3)	1.21337 (17)	0.44101 (6)	0.0603 (5)
O27	0.6826 (4)	0.83553 (19)	0.62793 (6)	0.0695 (6)
O28	0.5780 (4)	1.0114 (2)	0.65676 (6)	0.0706 (6)
O29	0.9180 (3)	0.83479 (16)	0.33116 (5)	0.0517 (4)
H25	1.046 (5)	1.211 (4)	0.2099 (10)	0.083 (11)*
H28	0.531 (7)	0.963 (4)	0.6783 (16)	0.128 (17)*
H29	0.987 (6)	0.783 (3)	0.3514 (10)	0.082 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0611 (16)	0.0530 (14)	0.0454 (13)	0.0175 (13)	−0.0064 (12)	0.0040 (11)
C2	0.0661 (17)	0.0428 (12)	0.0438 (12)	0.0024 (12)	−0.0054 (12)	0.0077 (10)
C3	0.0515 (13)	0.0513 (13)	0.0348 (11)	0.0041 (12)	−0.0061 (10)	0.0063 (10)
C4	0.0534 (13)	0.0468 (12)	0.0368 (11)	−0.0001 (12)	−0.0034 (10)	0.0014 (10)
C5	0.0441 (13)	0.0601 (15)	0.0425 (12)	−0.0048 (12)	−0.0090 (10)	0.0021 (11)
C6	0.0597 (16)	0.0633 (16)	0.0469 (13)	−0.0237 (14)	−0.0055 (12)	0.0006 (12)
C7	0.0642 (15)	0.0419 (12)	0.0394 (12)	−0.0134 (12)	0.0017 (11)	−0.0010 (10)
C8	0.0408 (11)	0.0418 (12)	0.0376 (10)	−0.0050 (10)	0.0036 (9)	0.0007 (9)
C9	0.0357 (11)	0.0395 (11)	0.0370 (11)	0.0003 (9)	0.0012 (8)	0.0004 (9)
C10	0.0377 (11)	0.0565 (14)	0.0432 (12)	0.0058 (12)	−0.0020 (10)	0.0028 (11)
C11	0.0586 (14)	0.0384 (11)	0.0402 (12)	0.0041 (11)	−0.0018 (11)	0.0030 (10)
C12	0.0509 (13)	0.0370 (11)	0.0372 (11)	0.0020 (11)	0.0032 (10)	−0.0044 (9)
C13	0.0398 (11)	0.0383 (11)	0.0324 (10)	0.0016 (9)	0.0051 (9)	0.0006 (9)
C14	0.0424 (11)	0.0358 (10)	0.0354 (10)	−0.0025 (10)	0.0052 (9)	0.0007 (9)
C15	0.0711 (17)	0.0357 (11)	0.0404 (12)	−0.0002 (12)	0.0052 (12)	0.0024 (9)
C16	0.0775 (18)	0.0435 (13)	0.0405 (12)	0.0163 (13)	0.0016 (12)	−0.0018 (10)
C17	0.0403 (11)	0.0430 (11)	0.0344 (10)	0.0046 (10)	0.0060 (9)	0.0015 (9)
C18	0.0424 (12)	0.0663 (16)	0.0401 (11)	0.0068 (12)	0.0072 (10)	0.0004 (11)
C19	0.0421 (14)	0.095 (2)	0.0669 (17)	0.0128 (16)	0.0030 (13)	0.0046 (18)
C20	0.0419 (11)	0.0393 (11)	0.0363 (10)	−0.0021 (10)	0.0030 (9)	−0.0010 (10)
C21	0.0471 (13)	0.0625 (16)	0.0492 (14)	−0.0070 (12)	−0.0005 (11)	−0.0095 (13)
C22	0.0485 (12)	0.0431 (12)	0.0340 (10)	−0.0051 (10)	0.0030 (9)	0.0009 (9)
C23	0.0609 (14)	0.0446 (12)	0.0398 (12)	0.0005 (12)	0.0097 (11)	0.0006 (10)
C24	0.0574 (14)	0.0526 (14)	0.0324 (11)	0.0014 (13)	0.0024 (10)	0.0005 (10)
O25	0.0641 (11)	0.0591 (11)	0.0379 (8)	−0.0029 (10)	0.0018 (8)	0.0070 (8)
O26	0.0708 (12)	0.0483 (10)	0.0619 (11)	−0.0164 (10)	−0.0105 (10)	0.0074 (9)
O27	0.0963 (15)	0.0564 (12)	0.0557 (11)	−0.0108 (12)	0.0254 (11)	0.0022 (9)
O28	0.0982 (16)	0.0664 (13)	0.0471 (10)	0.0147 (13)	0.0263 (11)	0.0054 (10)
O29	0.0739 (12)	0.0427 (9)	0.0383 (8)	0.0067 (9)	0.0004 (8)	−0.0018 (7)

Geometric parameters (Å, º) top

C1—C2	1.527 (4)	C13—C17	1.548 (3)
C1—C10	1.548 (4)	C13—C14	1.549 (3)
C1—H1A	0.9700	C14—C15	1.524 (3)
C1—H1B	0.9700	C14—H14	0.9800
C2—C3	1.515 (3)	C15—C16	1.529 (4)
C2—H2A	0.9700	C15—H15A	0.9700
C2—H2B	0.9700	C15—H15B	0.9700
C3—O25	1.447 (3)	C16—C17	1.562 (3)
C3—C4	1.504 (3)	C16—H16A	0.9700
C3—H3	0.9800	C16—H16B	0.9700
C4—C5	1.534 (3)	C17—C20	1.550 (3)
C4—H4A	0.9700	C17—H17	0.9800
C4—H4B	0.9700	C18—H18A	0.9600
C5—C6	1.534 (4)	C18—H18B	0.9600
C5—C10	1.554 (4)	C18—H18C	0.9600
C5—H5A	0.9800	C19—H19A	0.9600
C6—C7	1.520 (4)	C19—H19B	0.9600
C6—H6A	0.9700	C19—H19C	0.9600
C6—H6B	0.9700	C20—C21	1.534 (3)
C7—O29	1.448 (3)	C20—C22	1.538 (3)
C7—C8	1.529 (3)	C20—H20	0.9800
C7—H7	0.9800	C21—H21A	0.9600
C8—C14	1.514 (3)	C21—H21B	0.9600
C8—C9	1.551 (3)	C21—H21C	0.9600
C8—H8	0.9800	C22—C23	1.520 (3)
C9—C11	1.541 (3)	C22—H22A	0.9700
C9—C10	1.556 (3)	C22—H22B	0.9700
C9—H9	0.9800	C23—C24	1.497 (3)
C10—C19	1.539 (4)	C23—H23A	0.9700
C11—C12	1.523 (3)	C23—H23B	0.9700
C11—H11A	0.9700	C24—O27	1.208 (3)
C11—H11B	0.9700	C24—O28	1.323 (3)
C12—O26	1.215 (3)	O25—H25	0.92 (4)
C12—C13	1.509 (3)	O28—H28	0.92 (5)
C13—C18	1.541 (3)	O29—H29	0.96 (4)

C2—C1—C10	114.9 (2)	C18—C13—C17	113.27 (17)
C2—C1—H1A	108.5	C12—C13—C14	104.26 (16)
C10—C1—H1A	108.5	C18—C13—C14	113.02 (19)
C2—C1—H1B	108.5	C17—C13—C14	101.94 (17)
C10—C1—H1B	108.5	C8—C14—C15	119.4 (2)
H1A—C1—H1B	107.5	C8—C14—C13	113.82 (18)
C3—C2—C1	110.0 (2)	C15—C14—C13	102.63 (16)
C3—C2—H2A	109.7	C8—C14—H14	106.7
C1—C2—H2A	109.7	C15—C14—H14	106.7
C3—C2—H2B	109.7	C13—C14—H14	106.7
C1—C2—H2B	109.7	C14—C15—C16	103.5 (2)
H2A—C2—H2B	108.2	C14—C15—H15A	111.1
O25—C3—C4	107.2 (2)	C16—C15—H15A	111.1
O25—C3—C2	111.3 (2)	C14—C15—H15B	111.1
C4—C3—C2	111.47 (18)	C16—C15—H15B	111.1
O25—C3—H3	108.9	H15A—C15—H15B	109.0
C4—C3—H3	108.9	C15—C16—C17	106.9 (2)
C2—C3—H3	108.9	C15—C16—H16A	110.3
C3—C4—C5	112.8 (2)	C17—C16—H16A	110.3
C3—C4—H4A	109.0	C15—C16—H16B	110.3
C5—C4—H4A	109.0	C17—C16—H16B	110.3
C3—C4—H4B	109.0	H16A—C16—H16B	108.6
C5—C4—H4B	109.0	C13—C17—C20	118.56 (18)
H4A—C4—H4B	107.8	C13—C17—C16	104.45 (19)
C4—C5—C6	111.3 (2)	C20—C17—C16	115.8 (2)
C4—C5—C10	112.8 (2)	C13—C17—H17	105.7
C6—C5—C10	111.9 (2)	C20—C17—H17	105.7
C4—C5—H5A	106.8	C16—C17—H17	105.7
C6—C5—H5A	106.8	C13—C18—H18A	109.5
C10—C5—H5A	106.8	C13—C18—H18B	109.5
C7—C6—C5	114.9 (2)	H18A—C18—H18B	109.5
C7—C6—H6A	108.5	C13—C18—H18C	109.5
C5—C6—H6A	108.5	H18A—C18—H18C	109.5
C7—C6—H6B	108.5	H18B—C18—H18C	109.5
C5—C6—H6B	108.5	C10—C19—H19A	109.5
H6A—C6—H6B	107.5	C10—C19—H19B	109.5
O29—C7—C6	108.7 (2)	H19A—C19—H19B	109.5
O29—C7—C8	111.38 (19)	C10—C19—H19C	109.5
C6—C7—C8	111.5 (2)	H19A—C19—H19C	109.5
O29—C7—H7	108.4	H19B—C19—H19C	109.5
C6—C7—H7	108.4	C21—C20—C22	108.82 (19)
C8—C7—H7	108.4	C21—C20—C17	108.69 (19)
C14—C8—C7	113.17 (19)	C22—C20—C17	115.13 (19)
C14—C8—C9	109.37 (18)	C21—C20—H20	108.0
C7—C8—C9	111.05 (17)	C22—C20—H20	108.0
C14—C8—H8	107.7	C17—C20—H20	108.0
C7—C8—H8	107.7	C20—C21—H21A	109.5
C9—C8—H8	107.7	C20—C21—H21B	109.5
C11—C9—C8	113.21 (17)	H21A—C21—H21B	109.5
C11—C9—C10	113.57 (19)	C20—C21—H21C	109.5
C8—C9—C10	111.30 (19)	H21A—C21—H21C	109.5
C11—C9—H9	106.0	H21B—C21—H21C	109.5
C8—C9—H9	106.0	C23—C22—C20	112.80 (19)
C10—C9—H9	106.0	C23—C22—H22A	109.0
C19—C10—C1	106.9 (2)	C20—C22—H22A	109.0
C19—C10—C5	109.7 (2)	C23—C22—H22B	109.0
C1—C10—C5	108.26 (19)	C20—C22—H22B	109.0
C19—C10—C9	111.2 (2)	H22A—C22—H22B	107.8
C1—C10—C9	112.5 (2)	C24—C23—C22	113.6 (2)
C5—C10—C9	108.21 (19)	C24—C23—H23A	108.8
C12—C11—C9	114.78 (18)	C22—C23—H23A	108.8
C12—C11—H11A	108.6	C24—C23—H23B	108.8
C9—C11—H11A	108.6	C22—C23—H23B	108.8
C12—C11—H11B	108.6	H23A—C23—H23B	107.7
C9—C11—H11B	108.6	O27—C24—O28	123.1 (2)
H11A—C11—H11B	107.5	O27—C24—C23	123.5 (2)
O26—C12—C13	123.1 (2)	O28—C24—C23	113.3 (2)
O26—C12—C11	121.3 (2)	C3—O25—H25	106 (2)
C13—C12—C11	115.5 (2)	C24—O28—H28	112 (3)
C12—C13—C18	108.82 (19)	C7—O29—H29	106 (2)
C12—C13—C17	115.11 (19)

(III) top

Crystal data top

C₂₄H₃₆O₅	F(000) = 440
M_r = 404.53	D_x = 1.209 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 10.2677 (4) Å	Cell parameters from 2705 reflections
b = 7.1108 (2) Å	θ = 3.4–27.5°
c = 15.2270 (6) Å	µ = 0.08 mm⁻¹
β = 92.340 (1)°	T = 295 K
V = 1110.82 (7) Å³	Irregular, colourless
Z = 2	0.25 × 0.11 × 0.06 mm

Data collection top

Nonius Kappa CCD diffractometer	2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.5°, θ_min = 3.4°
ϕ scans and ω scans	h = −13→13
14953 measured reflections	k = −8→9
2721 independent reflections	l = −19→19

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0521P)² + 0.1088P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2721 reflections	Δρ_max = 0.15 e Å⁻³
273 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (14)

Crystal data top

C₂₄H₃₆O₅	V = 1110.82 (7) Å³
M_r = 404.53	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.2677 (4) Å	µ = 0.08 mm⁻¹
b = 7.1108 (2) Å	T = 295 K
c = 15.2270 (6) Å	0.25 × 0.11 × 0.06 mm
β = 92.340 (1)°

Data collection top

Nonius Kappa CCD diffractometer	2236 reflections with I > 2σ(I)
14953 measured reflections	R_int = 0.039
2721 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	Δρ_max = 0.15 e Å⁻³
S = 1.05	Δρ_min = −0.14 e Å⁻³
2721 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
273 parameters	Absolute structure parameter: 0.2 (14)
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.9533 (2)	0.1625 (4)	0.25059 (16)	0.0542 (6)
H1A	0.9865	0.0374	0.2634	0.065*
H1B	0.9234	0.1642	0.1893	0.065*
C2	1.0654 (2)	0.3026 (4)	0.26290 (15)	0.0550 (6)
H2A	1.1372	0.2669	0.2270	0.066*
H2B	1.0366	0.4277	0.2457	0.066*
C3	1.1076 (2)	0.3000 (4)	0.35795 (17)	0.0572 (6)
C4	1.0023 (2)	0.3467 (4)	0.41828 (16)	0.0615 (7)
H4A	0.9746	0.4756	0.4082	0.074*
H4B	1.0359	0.3369	0.4786	0.074*
C5	0.8837 (2)	0.2147 (4)	0.40487 (15)	0.0554 (6)
H5	0.9136	0.0890	0.4228	0.083*
C6	0.7745 (3)	0.2675 (5)	0.46631 (16)	0.0671 (8)
H6A	0.7171	0.1602	0.4715	0.081*
H6B	0.8131	0.2934	0.5243	0.081*
C7	0.6929 (3)	0.4378 (4)	0.43632 (15)	0.0591 (7)
H7	0.6172	0.4466	0.4733	0.089*
C8	0.6440 (2)	0.4129 (3)	0.34059 (13)	0.0439 (5)
H8	0.5898	0.2994	0.3374	0.066*
C9	0.7611 (2)	0.3816 (3)	0.28156 (13)	0.0391 (4)
H9	0.8216	0.4856	0.2941	0.059*
C10	0.8359 (2)	0.1984 (3)	0.30752 (15)	0.0466 (5)
C11	0.7236 (2)	0.3935 (4)	0.18204 (13)	0.0474 (5)
H11A	0.8020	0.4131	0.1498	0.057*
H11B	0.6857	0.2746	0.1630	0.057*
C12	0.62894 (19)	0.5484 (4)	0.15978 (13)	0.0439 (5)
C13	0.50485 (19)	0.5451 (3)	0.21048 (14)	0.0416 (5)
C14	0.5613 (2)	0.5767 (3)	0.30637 (14)	0.0451 (5)
H14	0.6181	0.6874	0.3053	0.068*
C15	0.4415 (2)	0.6312 (5)	0.35711 (17)	0.0617 (7)
H15A	0.4659	0.7110	0.4068	0.074*
H15B	0.3980	0.5201	0.3785	0.074*
C16	0.3528 (2)	0.7377 (5)	0.29039 (18)	0.0654 (7)
H16A	0.3486	0.8697	0.3061	0.078*
H16B	0.2653	0.6863	0.2897	0.078*
C17	0.4122 (2)	0.7146 (4)	0.19813 (15)	0.0483 (5)
H17	0.4660	0.8257	0.1880	0.072*
C18	0.4320 (2)	0.3557 (4)	0.20043 (17)	0.0520 (6)
H18A	0.3966	0.3437	0.1414	0.062*
H18B	0.3625	0.3515	0.2407	0.062*
H18C	0.4915	0.2543	0.2130	0.062*
C19	0.7487 (3)	0.0228 (4)	0.2959 (2)	0.0697 (8)
H19A	0.6731	0.0366	0.3304	0.084*
H19B	0.7966	−0.0867	0.3150	0.084*
H19C	0.7221	0.0093	0.2350	0.084*
C20	0.3070 (2)	0.7059 (4)	0.12353 (16)	0.0527 (6)
H20	0.2474	0.6027	0.1364	0.079*
C21	0.3640 (3)	0.6674 (5)	0.03331 (17)	0.0696 (8)
H21A	0.4221	0.7677	0.0190	0.084*
H21B	0.2945	0.6599	−0.0107	0.084*
H21C	0.4111	0.5508	0.0354	0.084*
C22	0.2280 (2)	0.8896 (4)	0.1212 (2)	0.0664 (7)
H22A	0.2046	0.9191	0.1807	0.080*
H22B	0.2841	0.9899	0.1018	0.080*
C23	0.1042 (2)	0.8902 (5)	0.0627 (2)	0.0708 (8)
H23A	0.0805	1.0197	0.0501	0.085*
H23B	0.1231	0.8307	0.0074	0.085*
C24	−0.0105 (2)	0.7936 (4)	0.09961 (16)	0.0505 (5)
O25	1.21663 (18)	0.2517 (4)	0.38315 (13)	0.0844 (7)
O26	0.65618 (14)	0.6763 (3)	0.11074 (11)	0.0599 (5)
O27	−0.00987 (17)	0.7082 (3)	0.16702 (14)	0.0729 (6)
O28	−0.11792 (17)	0.8183 (3)	0.04931 (13)	0.0657 (5)
H28	−0.181 (3)	0.767 (6)	0.074 (2)	0.092 (12)*
O29	0.7630 (2)	0.6109 (3)	0.44259 (13)	0.0698 (6)
H29	0.772 (4)	0.652 (7)	0.505 (3)	0.116 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0516 (12)	0.0525 (14)	0.0581 (13)	0.0079 (11)	−0.0024 (10)	−0.0050 (11)
C2	0.0474 (11)	0.0627 (15)	0.0551 (13)	0.0012 (12)	0.0041 (10)	0.0131 (13)
C3	0.0475 (12)	0.0629 (15)	0.0605 (14)	−0.0099 (12)	−0.0065 (10)	0.0131 (13)
C4	0.0585 (14)	0.0724 (18)	0.0523 (14)	−0.0051 (13)	−0.0119 (11)	−0.0023 (12)
C5	0.0562 (12)	0.0586 (15)	0.0513 (13)	−0.0032 (12)	0.0013 (10)	0.0134 (12)
C6	0.0692 (16)	0.086 (2)	0.0463 (13)	−0.0013 (15)	0.0090 (11)	0.0175 (14)
C7	0.0580 (14)	0.0792 (19)	0.0405 (12)	−0.0064 (13)	0.0073 (10)	0.0008 (12)
C8	0.0426 (10)	0.0499 (12)	0.0397 (10)	−0.0086 (9)	0.0073 (8)	−0.0006 (9)
C9	0.0373 (10)	0.0421 (11)	0.0379 (10)	−0.0075 (9)	0.0030 (8)	−0.0013 (9)
C10	0.0470 (11)	0.0416 (11)	0.0511 (12)	−0.0082 (10)	0.0006 (9)	0.0019 (10)
C11	0.0411 (10)	0.0617 (14)	0.0395 (11)	−0.0005 (10)	0.0030 (8)	−0.0068 (10)
C12	0.0368 (10)	0.0585 (13)	0.0365 (10)	−0.0055 (10)	0.0015 (8)	−0.0053 (10)
C13	0.0347 (9)	0.0468 (11)	0.0437 (11)	−0.0072 (9)	0.0053 (8)	−0.0039 (10)
C14	0.0418 (10)	0.0529 (13)	0.0411 (11)	−0.0072 (9)	0.0063 (8)	−0.0083 (9)
C15	0.0514 (13)	0.0799 (18)	0.0547 (13)	0.0008 (13)	0.0146 (11)	−0.0118 (14)
C16	0.0528 (13)	0.0752 (19)	0.0689 (16)	0.0067 (13)	0.0121 (11)	−0.0145 (14)
C17	0.0396 (10)	0.0485 (12)	0.0571 (13)	−0.0040 (10)	0.0055 (9)	−0.0023 (11)
C18	0.0439 (11)	0.0514 (13)	0.0604 (14)	−0.0116 (10)	−0.0003 (10)	−0.0049 (11)
C19	0.0667 (16)	0.0411 (13)	0.101 (2)	−0.0114 (13)	−0.0031 (15)	−0.0005 (14)
C20	0.0369 (10)	0.0568 (14)	0.0644 (14)	−0.0021 (11)	0.0021 (9)	0.0054 (12)
C21	0.0535 (13)	0.095 (2)	0.0601 (15)	0.0012 (15)	−0.0010 (11)	0.0096 (15)
C22	0.0446 (12)	0.0576 (15)	0.097 (2)	−0.0032 (12)	0.0006 (13)	0.0140 (15)
C23	0.0437 (12)	0.0778 (19)	0.091 (2)	0.0027 (13)	0.0058 (12)	0.0347 (17)
C24	0.0441 (11)	0.0453 (12)	0.0623 (13)	0.0053 (10)	0.0066 (10)	0.0064 (12)
O25	0.0504 (9)	0.128 (2)	0.0738 (12)	−0.0005 (12)	−0.0075 (8)	0.0338 (14)
O26	0.0403 (8)	0.0772 (13)	0.0627 (10)	−0.0043 (9)	0.0080 (7)	0.0201 (10)
O27	0.0613 (10)	0.0763 (14)	0.0811 (13)	−0.0040 (11)	0.0019 (9)	0.0282 (12)
O28	0.0431 (9)	0.0865 (14)	0.0676 (11)	−0.0015 (10)	0.0038 (8)	0.0170 (11)
O29	0.0794 (13)	0.0778 (14)	0.0518 (10)	−0.0098 (11)	−0.0037 (9)	−0.0160 (9)

Geometric parameters (Å, º) top

C1—C2	1.528 (3)	C13—C18	1.545 (3)
C1—C10	1.534 (3)	C13—C14	1.565 (3)
C1—H1A	0.9700	C14—C15	1.529 (3)
C1—H1B	0.9700	C14—H14	0.9800
C2—C3	1.494 (3)	C15—C16	1.536 (4)
C2—H2A	0.9700	C15—H15A	0.9700
C2—H2B	0.9700	C15—H15B	0.9700
C3—O25	1.218 (3)	C16—C17	1.563 (3)
C3—C4	1.485 (4)	C16—H16A	0.9700
C4—C5	1.544 (4)	C16—H16B	0.9700
C4—H4A	0.9700	C17—C20	1.537 (3)
C4—H4B	0.9700	C17—H17	0.9800
C5—C6	1.536 (4)	C18—H18A	0.9600
C5—C10	1.547 (3)	C18—H18B	0.9600
C5—H5	0.9800	C18—H18C	0.9600
C6—C7	1.532 (4)	C19—H19A	0.9600
C6—H6A	0.9700	C19—H19B	0.9600
C6—H6B	0.9700	C19—H19C	0.9600
C7—O29	1.427 (4)	C20—C22	1.537 (4)
C7—C8	1.533 (3)	C20—C21	1.540 (4)
C7—H7	0.9800	C20—H20	0.9800
C8—C14	1.521 (3)	C21—H21A	0.9600
C8—C9	1.547 (3)	C21—H21B	0.9600
C8—H8	0.9800	C21—H21C	0.9600
C9—C11	1.551 (3)	C22—C23	1.521 (4)
C9—C10	1.555 (3)	C22—H22A	0.9700
C9—H9	0.9800	C22—H22B	0.9700
C10—C19	1.543 (3)	C23—C24	1.493 (4)
C11—C12	1.498 (3)	C23—H23A	0.9700
C11—H11A	0.9700	C23—H23B	0.9700
C11—H11B	0.9700	C24—O27	1.193 (3)
C12—O26	1.217 (3)	C24—O28	1.328 (3)
C12—C13	1.517 (3)	O28—H28	0.85 (4)
C13—C17	1.543 (3)	O29—H29	0.99 (4)

C2—C1—C10	115.3 (2)	C12—C13—C14	100.71 (15)
C2—C1—H1A	108.5	C17—C13—C14	101.80 (18)
C10—C1—H1A	108.5	C18—C13—C14	112.15 (19)
C2—C1—H1B	108.5	C8—C14—C15	118.0 (2)
C10—C1—H1B	108.5	C8—C14—C13	112.94 (18)
H1A—C1—H1B	107.5	C15—C14—C13	103.46 (17)
C3—C2—C1	107.3 (2)	C8—C14—H14	107.3
C3—C2—H2A	110.2	C15—C14—H14	107.3
C1—C2—H2A	110.2	C13—C14—H14	107.3
C3—C2—H2B	110.2	C14—C15—C16	104.95 (19)
C1—C2—H2B	110.2	C14—C15—H15A	110.8
H2A—C2—H2B	108.5	C16—C15—H15A	110.8
O25—C3—C4	123.5 (2)	C14—C15—H15B	110.8
O25—C3—C2	122.4 (3)	C16—C15—H15B	110.8
C4—C3—C2	114.0 (2)	H15A—C15—H15B	108.8
C3—C4—C5	111.9 (2)	C15—C16—C17	107.50 (19)
C3—C4—H4A	109.2	C15—C16—H16A	110.2
C5—C4—H4A	109.2	C17—C16—H16A	110.2
C3—C4—H4B	109.2	C15—C16—H16B	110.2
C5—C4—H4B	109.2	C17—C16—H16B	110.2
H4A—C4—H4B	107.9	H16A—C16—H16B	108.5
C6—C5—C4	111.2 (2)	C20—C17—C13	118.0 (2)
C6—C5—C10	113.0 (2)	C20—C17—C16	112.37 (18)
C4—C5—C10	112.93 (19)	C13—C17—C16	103.5 (2)
C6—C5—H5	106.4	C20—C17—H17	107.5
C4—C5—H5	106.4	C13—C17—H17	107.5
C10—C5—H5	106.4	C16—C17—H17	107.5
C7—C6—C5	114.6 (2)	C13—C18—H18A	109.5
C7—C6—H6A	108.6	C13—C18—H18B	109.5
C5—C6—H6A	108.6	H18A—C18—H18B	109.5
C7—C6—H6B	108.6	C13—C18—H18C	109.5
C5—C6—H6B	108.6	H18A—C18—H18C	109.5
H6A—C6—H6B	107.6	H18B—C18—H18C	109.5
O29—C7—C6	113.2 (2)	C10—C19—H19A	109.5
O29—C7—C8	108.0 (2)	C10—C19—H19B	109.5
C6—C7—C8	110.3 (2)	H19A—C19—H19B	109.5
O29—C7—H7	108.4	C10—C19—H19C	109.5
C6—C7—H7	108.4	H19A—C19—H19C	109.5
C8—C7—H7	108.4	H19B—C19—H19C	109.5
C14—C8—C7	113.20 (19)	C17—C20—C22	109.7 (2)
C14—C8—C9	110.32 (17)	C17—C20—C21	112.64 (18)
C7—C8—C9	109.69 (18)	C22—C20—C21	110.5 (2)
C14—C8—H8	107.8	C17—C20—H20	108.0
C7—C8—H8	107.8	C22—C20—H20	108.0
C9—C8—H8	107.8	C21—C20—H20	108.0
C8—C9—C11	113.10 (17)	C20—C21—H21A	109.5
C8—C9—C10	111.15 (17)	C20—C21—H21B	109.5
C11—C9—C10	113.25 (18)	H21A—C21—H21B	109.5
C8—C9—H9	106.2	C20—C21—H21C	109.5
C11—C9—H9	106.2	H21A—C21—H21C	109.5
C10—C9—H9	106.2	H21B—C21—H21C	109.5
C1—C10—C19	105.4 (2)	C23—C22—C20	116.3 (3)
C1—C10—C5	109.17 (18)	C23—C22—H22A	108.2
C19—C10—C5	109.3 (2)	C20—C22—H22A	108.2
C1—C10—C9	112.79 (19)	C23—C22—H22B	108.2
C19—C10—C9	111.70 (18)	C20—C22—H22B	108.2
C5—C10—C9	108.37 (19)	H22A—C22—H22B	107.4
C12—C11—C9	113.22 (18)	C24—C23—C22	115.6 (2)
C12—C11—H11A	108.9	C24—C23—H23A	108.4
C9—C11—H11A	108.9	C22—C23—H23A	108.4
C12—C11—H11B	108.9	C24—C23—H23B	108.4
C9—C11—H11B	108.9	C22—C23—H23B	108.4
H11A—C11—H11B	107.7	H23A—C23—H23B	107.4
O26—C12—C11	121.67 (19)	O27—C24—O28	122.6 (2)
O26—C12—C13	122.9 (2)	O27—C24—C23	125.5 (2)
C11—C12—C13	115.11 (19)	O28—C24—C23	111.8 (2)
C12—C13—C17	116.92 (19)	C24—O28—H28	109 (2)
C12—C13—C18	112.11 (19)	C7—O29—H29	110 (3)
C17—C13—C18	112.04 (16)

(IV-alpha) top

Crystal data top

C₂₄H₃₆O₅	D_x = 1.197 Mg m⁻³
M_r = 404.53	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3622 reflections
a = 8.4953 (1) Å	θ = 4.0–30.0°
b = 12.7060 (2) Å	µ = 0.08 mm⁻¹
c = 20.8011 (3) Å	T = 295 K
V = 2245.30 (5) Å³	Prism, colourless
Z = 4	0.45 × 0.35 × 0.32 mm
F(000) = 880

Data collection top

Nonius Kappa CCD diffractometer	3189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 30.0°, θ_min = 4.0°
ϕ scans and ω scans	h = −11→11
26164 measured reflections	k = −17→17
3664 independent reflections	l = −29→29

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	All H-atom parameters refined
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0967P)² + 0.2322P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.009
3664 reflections	Δρ_max = 0.45 e Å⁻³
406 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.3 (15)

Crystal data top

C₂₄H₃₆O₅	V = 2245.30 (5) Å³
M_r = 404.53	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.4953 (1) Å	µ = 0.08 mm⁻¹
b = 12.7060 (2) Å	T = 295 K
c = 20.8011 (3) Å	0.45 × 0.35 × 0.32 mm

Data collection top

Nonius Kappa CCD diffractometer	3189 reflections with I > 2σ(I)
26164 measured reflections	R_int = 0.035
3664 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	All H-atom parameters refined
wR(F²) = 0.146	Δρ_max = 0.45 e Å⁻³
S = 1.06	Δρ_min = −0.32 e Å⁻³
3664 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
406 parameters	Absolute structure parameter: −0.3 (15)
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.0476 (3)	0.0840 (2)	0.09477 (11)	0.0472 (5)
C2	−0.2061 (3)	0.1052 (2)	0.12646 (13)	0.0541 (6)
C3	−0.2663 (3)	0.2126 (3)	0.10838 (12)	0.0548 (6)
C4	−0.1503 (3)	0.2999 (2)	0.11661 (13)	0.0528 (6)
C5	0.0102 (3)	0.2751 (2)	0.08602 (10)	0.0438 (5)
C6	0.1239 (3)	0.3673 (2)	0.09973 (13)	0.0527 (6)
C7	0.1644 (3)	0.36698 (17)	0.17024 (11)	0.0412 (4)
C8	0.2422 (2)	0.26719 (15)	0.19326 (9)	0.0332 (4)
C9	0.1270 (2)	0.17386 (15)	0.17969 (8)	0.0316 (3)
C10	0.0794 (2)	0.16743 (18)	0.10744 (9)	0.0381 (4)
C11	0.1927 (3)	0.06965 (15)	0.20612 (9)	0.0363 (4)
C12	0.2444 (2)	0.07523 (14)	0.27686 (8)	0.0323 (4)
C13	0.3626 (2)	0.16506 (13)	0.28733 (8)	0.0298 (3)
C14	0.2854 (2)	0.26884 (14)	0.26447 (8)	0.0312 (4)
C15	0.3989 (3)	0.35427 (16)	0.28795 (12)	0.0441 (5)
C16	0.4646 (3)	0.31082 (17)	0.35148 (12)	0.0471 (5)
C17	0.4041 (2)	0.19527 (14)	0.35805 (9)	0.0317 (4)
C18	0.5152 (3)	0.14028 (19)	0.25028 (11)	0.0398 (4)
C19	0.2208 (3)	0.1395 (3)	0.06451 (11)	0.0531 (6)
C20	0.5209 (3)	0.12555 (16)	0.39534 (10)	0.0370 (4)
C21	0.4644 (4)	0.01176 (18)	0.40226 (11)	0.0506 (6)
C22	0.5581 (3)	0.1717 (2)	0.46237 (10)	0.0423 (5)
C23	0.4158 (3)	0.1829 (3)	0.50623 (11)	0.0555 (6)
C24	0.4543 (4)	0.2252 (3)	0.57183 (13)	0.0617 (7)
O25	−0.3978 (2)	0.2283 (3)	0.08818 (13)	0.0812 (8)
O26	0.1104 (2)	0.09003 (13)	0.31787 (7)	0.0417 (3)
O27	0.4346 (7)	0.1806 (3)	0.62092 (13)	0.1301 (18)
O28	0.5105 (3)	0.32179 (19)	0.56985 (11)	0.0726 (6)
O29	0.1281 (3)	0.43893 (13)	0.20588 (9)	0.0564 (5)
H1A	−0.016 (4)	0.023 (2)	0.1072 (14)	0.047 (8)*
H1B	−0.064 (4)	0.081 (3)	0.0449 (16)	0.065 (9)*
H2A	−0.189 (5)	0.108 (3)	0.1786 (19)	0.076 (10)*
H2B	−0.288 (6)	0.059 (3)	0.113 (2)	0.092 (13)*
H4A	−0.145 (4)	0.312 (2)	0.1636 (14)	0.046 (7)*
H4B	−0.195 (5)	0.366 (3)	0.0975 (19)	0.078 (11)*
H5	0.004 (3)	0.2680 (19)	0.0388 (11)	0.034 (6)*
H6A	0.230 (6)	0.351 (4)	0.072 (2)	0.091 (13)*
H6B	0.078 (5)	0.433 (3)	0.0840 (19)	0.081 (11)*
H8	0.331 (3)	0.258 (2)	0.1710 (13)	0.037 (6)*
H9	0.034 (4)	0.187 (2)	0.2040 (13)	0.045 (7)*
H11A	0.282 (4)	0.047 (2)	0.1781 (14)	0.045 (7)*
H11B	0.116 (4)	0.017 (2)	0.2000 (13)	0.044 (7)*
H12	0.295 (3)	0.010 (2)	0.2884 (12)	0.036 (6)*
H14	0.187 (3)	0.2826 (19)	0.2877 (11)	0.030 (5)*
H15A	0.488 (4)	0.360 (2)	0.2529 (15)	0.049 (7)*
H15B	0.347 (5)	0.416 (3)	0.2883 (17)	0.073 (10)*
H16A	0.429 (4)	0.345 (3)	0.3921 (16)	0.058 (8)*
H16B	0.585 (5)	0.310 (3)	0.3502 (17)	0.076 (11)*
H17	0.309 (3)	0.2094 (19)	0.3817 (11)	0.029 (5)*
H18A	0.589 (4)	0.192 (2)	0.2587 (13)	0.040 (6)*
H18B	0.557 (4)	0.080 (3)	0.2612 (15)	0.060 (9)*
H18C	0.497 (4)	0.132 (3)	0.2011 (16)	0.063 (9)*
H19A	0.313 (5)	0.178 (3)	0.0743 (19)	0.076 (11)*
H19B	0.245 (4)	0.073 (3)	0.0677 (17)	0.063 (10)*
H19C	0.179 (5)	0.147 (3)	0.0209 (17)	0.067 (9)*
H20	0.621 (3)	0.132 (2)	0.3723 (12)	0.039 (6)*
H21A	0.359 (4)	0.011 (2)	0.4173 (14)	0.047 (7)*
H21B	0.454 (4)	−0.023 (2)	0.3597 (15)	0.057 (8)*
H21C	0.521 (5)	−0.033 (3)	0.4342 (19)	0.080 (11)*
H22A	0.640 (3)	0.125 (2)	0.4790 (12)	0.035 (6)*
H22B	0.609 (5)	0.233 (3)	0.4546 (17)	0.065 (9)*
H23A	0.335 (5)	0.234 (3)	0.4856 (18)	0.073 (11)*
H23B	0.351 (10)	0.117 (5)	0.506 (3)	0.15 (2)*
H26	0.031 (5)	0.058 (3)	0.3046 (19)	0.078 (11)*
H28	0.545 (5)	0.330 (3)	0.615 (2)	0.077 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0431 (11)	0.0597 (14)	0.0389 (10)	−0.0059 (11)	−0.0065 (9)	−0.0069 (10)
C2	0.0426 (12)	0.0700 (16)	0.0497 (12)	−0.0132 (12)	−0.0016 (10)	0.0047 (11)
C3	0.0345 (11)	0.0832 (18)	0.0466 (11)	−0.0005 (12)	0.0014 (9)	0.0114 (12)
C4	0.0405 (11)	0.0628 (15)	0.0552 (13)	0.0078 (11)	−0.0063 (10)	0.0060 (11)
C5	0.0385 (10)	0.0585 (12)	0.0345 (9)	−0.0010 (10)	−0.0042 (8)	0.0085 (8)
C6	0.0518 (13)	0.0568 (14)	0.0494 (12)	−0.0081 (11)	−0.0107 (11)	0.0209 (11)
C7	0.0370 (9)	0.0396 (10)	0.0470 (10)	−0.0024 (8)	−0.0059 (8)	0.0107 (8)
C8	0.0327 (9)	0.0334 (8)	0.0336 (8)	0.0018 (7)	−0.0007 (7)	0.0020 (7)
C9	0.0321 (8)	0.0356 (8)	0.0271 (7)	−0.0003 (7)	0.0015 (7)	−0.0025 (6)
C10	0.0341 (9)	0.0528 (11)	0.0274 (7)	0.0001 (8)	0.0009 (7)	−0.0013 (8)
C11	0.0452 (10)	0.0321 (8)	0.0317 (8)	0.0003 (8)	−0.0038 (8)	−0.0065 (7)
C12	0.0408 (9)	0.0262 (8)	0.0300 (7)	−0.0013 (7)	−0.0007 (7)	−0.0032 (6)
C13	0.0333 (8)	0.0259 (7)	0.0303 (7)	0.0024 (6)	−0.0007 (7)	−0.0019 (6)
C14	0.0333 (9)	0.0261 (7)	0.0342 (8)	0.0006 (7)	−0.0030 (7)	−0.0021 (6)
C15	0.0518 (12)	0.0273 (8)	0.0531 (11)	−0.0052 (8)	−0.0105 (11)	0.0009 (8)
C16	0.0539 (13)	0.0335 (9)	0.0540 (12)	−0.0089 (9)	−0.0158 (11)	−0.0024 (9)
C17	0.0324 (9)	0.0286 (8)	0.0342 (8)	0.0020 (7)	−0.0048 (7)	−0.0039 (6)
C18	0.0353 (10)	0.0420 (10)	0.0420 (9)	0.0079 (9)	0.0047 (8)	−0.0022 (8)
C19	0.0426 (12)	0.0830 (19)	0.0337 (9)	0.0034 (13)	0.0064 (9)	−0.0115 (11)
C20	0.0358 (9)	0.0402 (10)	0.0349 (8)	0.0063 (8)	−0.0044 (8)	−0.0021 (7)
C21	0.0720 (18)	0.0387 (10)	0.0413 (10)	0.0065 (11)	−0.0145 (12)	0.0003 (9)
C22	0.0352 (10)	0.0502 (12)	0.0415 (10)	0.0032 (9)	−0.0115 (8)	−0.0061 (9)
C23	0.0443 (12)	0.0807 (18)	0.0414 (11)	0.0043 (13)	−0.0078 (10)	−0.0198 (12)
C24	0.0687 (17)	0.0679 (16)	0.0484 (12)	0.0124 (15)	−0.0148 (13)	−0.0142 (11)
O25	0.0368 (9)	0.119 (2)	0.0877 (15)	−0.0061 (12)	−0.0120 (10)	0.0315 (15)
O26	0.0439 (8)	0.0446 (8)	0.0367 (6)	−0.0153 (7)	0.0049 (6)	−0.0086 (6)
O27	0.237 (5)	0.098 (2)	0.0557 (13)	−0.031 (3)	−0.033 (2)	−0.0001 (13)
O28	0.0904 (17)	0.0728 (13)	0.0546 (10)	−0.0029 (13)	−0.0162 (11)	−0.0093 (9)
O29	0.0647 (11)	0.0397 (8)	0.0649 (10)	0.0153 (8)	−0.0139 (9)	0.0029 (7)

Geometric parameters (Å, º) top

C1—C2	1.523 (4)	C13—C14	1.547 (2)
C1—C10	1.536 (3)	C13—C17	1.561 (2)
C1—H1A	0.86 (3)	C14—C15	1.532 (3)
C1—H1B	1.05 (3)	C14—H14	0.98 (3)
C2—C3	1.505 (4)	C15—C16	1.537 (3)
C2—H2A	1.09 (4)	C15—H15A	1.06 (3)
C2—H2B	0.95 (5)	C15—H15B	0.90 (4)
C3—O25	1.210 (3)	C16—C17	1.561 (3)
C3—C4	1.493 (4)	C16—H16A	0.99 (3)
C4—C5	1.538 (3)	C16—H16B	1.02 (4)
C4—H4A	0.99 (3)	C17—C20	1.540 (3)
C4—H4B	1.00 (4)	C17—H17	0.96 (2)
C5—C6	1.545 (4)	C18—H18A	0.92 (3)
C5—C10	1.554 (3)	C18—H18B	0.88 (4)
C5—H5	0.99 (2)	C18—H18C	1.04 (3)
C6—C7	1.507 (3)	C19—H19A	0.95 (5)
C6—H6A	1.09 (5)	C19—H19B	0.87 (4)
C6—H6B	0.98 (4)	C19—H19C	0.98 (4)
C7—O29	1.217 (3)	C20—C21	1.530 (3)
C7—C8	1.508 (3)	C20—C22	1.545 (3)
C8—C14	1.526 (2)	C20—H20	0.98 (3)
C8—C9	1.563 (3)	C21—H21A	0.95 (3)
C8—H8	0.89 (3)	C21—H21B	0.99 (3)
C9—C11	1.538 (3)	C21—H21C	1.00 (4)
C9—C10	1.559 (2)	C22—C23	1.522 (4)
C9—H9	0.96 (3)	C22—H22A	0.98 (3)
C10—C19	1.538 (3)	C22—H22B	0.90 (4)
C11—C12	1.537 (2)	C23—C24	1.503 (3)
C11—H11A	1.00 (3)	C23—H23A	1.03 (4)
C11—H11B	0.94 (3)	C23—H23B	1.00 (7)
C12—O26	1.435 (3)	C24—O27	1.180 (4)
C12—C13	1.536 (3)	C24—O28	1.317 (4)
C12—H12	0.96 (3)	O26—H26	0.84 (4)
C13—C18	1.541 (3)	O28—H28	0.98 (4)

C2—C1—C10	115.2 (2)	C12—C13—C17	117.67 (15)
C2—C1—H1A	108 (2)	C18—C13—C17	109.35 (16)
C10—C1—H1A	110 (2)	C14—C13—C17	100.12 (13)
C2—C1—H1B	109 (2)	C8—C14—C15	118.07 (17)
C10—C1—H1B	107 (2)	C8—C14—C13	112.85 (14)
H1A—C1—H1B	108 (3)	C15—C14—C13	103.85 (15)
C3—C2—C1	110.6 (2)	C8—C14—H14	106.1 (14)
C3—C2—H2A	105 (2)	C15—C14—H14	104.6 (14)
C1—C2—H2A	109 (2)	C13—C14—H14	111.1 (14)
C3—C2—H2B	104 (3)	C14—C15—C16	104.37 (16)
C1—C2—H2B	115 (3)	C14—C15—H15A	106.5 (17)
H2A—C2—H2B	113 (4)	C16—C15—H15A	110.9 (17)
O25—C3—C4	121.7 (3)	C14—C15—H15B	108 (3)
O25—C3—C2	123.4 (3)	C16—C15—H15B	119 (2)
C4—C3—C2	114.9 (2)	H15A—C15—H15B	107 (3)
C3—C4—C5	112.7 (2)	C15—C16—C17	107.06 (16)
C3—C4—H4A	104.8 (17)	C15—C16—H16A	118 (2)
C5—C4—H4A	113.5 (18)	C17—C16—H16A	103.5 (19)
C3—C4—H4B	109 (2)	C15—C16—H16B	110 (2)
C5—C4—H4B	110 (2)	C17—C16—H16B	109 (2)
H4A—C4—H4B	106 (3)	H16A—C16—H16B	109 (3)
C4—C5—C6	108.8 (2)	C20—C17—C13	118.62 (15)
C4—C5—C10	113.39 (19)	C20—C17—C16	111.89 (16)
C6—C5—C10	112.23 (18)	C13—C17—C16	102.91 (15)
C4—C5—H5	112.5 (15)	C20—C17—H17	113.0 (14)
C6—C5—H5	106.6 (15)	C13—C17—H17	109.7 (14)
C10—C5—H5	103.0 (14)	C16—C17—H17	98.4 (14)
C7—C6—C5	108.70 (19)	C13—C18—H18A	109.1 (17)
C7—C6—H6A	109 (2)	C13—C18—H18B	113 (2)
C5—C6—H6A	106 (2)	H18A—C18—H18B	107 (3)
C7—C6—H6B	115 (2)	C13—C18—H18C	113 (2)
C5—C6—H6B	110 (3)	H18A—C18—H18C	111 (3)
H6A—C6—H6B	108 (3)	H18B—C18—H18C	103 (3)
O29—C7—C6	122.2 (2)	C10—C19—H19A	114 (2)
O29—C7—C8	123.3 (2)	C10—C19—H19B	111 (3)
C6—C7—C8	114.3 (2)	H19A—C19—H19B	107 (4)
C7—C8—C14	113.70 (17)	C10—C19—H19C	103 (2)
C7—C8—C9	107.83 (15)	H19A—C19—H19C	117 (3)
C14—C8—C9	109.64 (15)	H19B—C19—H19C	104 (3)
C7—C8—H8	108.3 (17)	C21—C20—C17	112.88 (18)
C14—C8—H8	107.7 (17)	C21—C20—C22	109.74 (18)
C9—C8—H8	109.7 (17)	C17—C20—C22	111.60 (16)
C11—C9—C10	113.18 (15)	C21—C20—H20	113.5 (16)
C11—C9—C8	111.18 (15)	C17—C20—H20	105.2 (15)
C10—C9—C8	112.10 (15)	C22—C20—H20	103.4 (16)
C11—C9—H9	105.2 (17)	C20—C21—H21A	109.8 (18)
C10—C9—H9	107.7 (17)	C20—C21—H21B	111.1 (19)
C8—C9—H9	107.0 (16)	H21A—C21—H21B	102 (3)
C1—C10—C19	106.9 (2)	C20—C21—H21C	117 (2)
C1—C10—C5	107.00 (19)	H21A—C21—H21C	103 (3)
C19—C10—C5	109.4 (2)	H21B—C21—H21C	113 (3)
C1—C10—C9	112.58 (17)	C23—C22—C20	114.44 (18)
C19—C10—C9	111.68 (17)	C23—C22—H22A	114.3 (15)
C5—C10—C9	109.17 (17)	C20—C22—H22A	103.5 (15)
C12—C11—C9	113.96 (15)	C23—C22—H22B	114 (2)
C12—C11—H11A	110.7 (16)	C20—C22—H22B	105 (2)
C9—C11—H11A	108.6 (16)	H22A—C22—H22B	104 (3)
C12—C11—H11B	111.1 (16)	C24—C23—C22	113.9 (2)
C9—C11—H11B	108.3 (17)	C24—C23—H23A	107 (2)
H11A—C11—H11B	104 (2)	C22—C23—H23A	110 (2)
O26—C12—C13	109.68 (14)	C24—C23—H23B	115 (3)
O26—C12—C11	110.40 (17)	C22—C23—H23B	111 (4)
C13—C12—C11	110.90 (15)	H23A—C23—H23B	99 (5)
O26—C12—H12	108.6 (15)	O27—C24—O28	121.7 (3)
C13—C12—H12	108.2 (16)	O27—C24—C23	125.6 (3)
C11—C12—H12	109.0 (15)	O28—C24—C23	112.6 (3)
C12—C13—C18	109.11 (15)	C12—O26—H26	112 (3)
C12—C13—C14	108.24 (15)	C24—O28—H28	101 (2)
C18—C13—C14	112.13 (16)

(IV-beta) top

Crystal data top

C₂₄H₃₆O₅·1/2(H₂O)	F(000) = 1800
M_r = 413.54	D_x = 1.172 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71070 Å
a = 26.6049 (4) Å	Cell parameters from 5260 reflections
b = 7.7044 (1) Å	θ = 4.2–27.5°
c = 22.9126 (3) Å	µ = 0.08 mm⁻¹
β = 93.424 (1)°	T = 295 K
V = 4688.1 (1) Å³	Irregular, colourless
Z = 8	0.35 × 0.12 × 0.08 mm

Data collection top

Nonius Kappa CCD diffractometer	4381 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 4.2°
ϕ scans and ω scans	h = −33→34
26846 measured reflections	k = −9→8
5683 independent reflections	l = −29→29

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.1005P)² + 1.4815P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.004
5683 reflections	Δρ_max = 0.35 e Å⁻³
567 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.6 (15)

Crystal data top

C₂₄H₃₆O₅·1/2(H₂O)	V = 4688.1 (1) Å³
M_r = 413.54	Z = 8
Monoclinic, C2	Mo Kα radiation
a = 26.6049 (4) Å	µ = 0.08 mm⁻¹
b = 7.7044 (1) Å	T = 295 K
c = 22.9126 (3) Å	0.35 × 0.12 × 0.08 mm
β = 93.424 (1)°

Data collection top

Nonius Kappa CCD diffractometer	4381 reflections with I > 2σ(I)
26846 measured reflections	R_int = 0.034
5683 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.166	Δρ_max = 0.35 e Å⁻³
S = 1.01	Δρ_min = −0.27 e Å⁻³
5683 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
567 parameters	Absolute structure parameter: 1.6 (15)
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O25A	0.71735 (10)	0.8309 (6)	0.54387 (13)	0.0830 (8)
O29A	0.87669 (12)	1.2413 (5)	0.67907 (14)	0.0822 (8)
O26A	0.90450 (9)	0.5944 (5)	0.71548 (10)	0.0573 (6)
H26A	0.8893 (14)	0.509 (6)	0.7055 (16)	0.055 (10)*
O27A	1.17998 (13)	0.7213 (8)	0.8870 (2)	0.1363 (18)
O28A	1.12331 (11)	0.9015 (6)	0.84937 (15)	0.0887 (9)
H28A	1.1560 (18)	0.987 (7)	0.8418 (19)	0.090 (14)*
C1A	0.84182 (14)	0.7208 (7)	0.52203 (14)	0.0645 (9)
H11	0.8315	0.7471	0.4817	0.077*
H12	0.8634	0.6193	0.5221	0.077*
C2A	0.79504 (14)	0.6771 (6)	0.55480 (14)	0.0616 (8)
H21	0.7765	0.5839	0.5349	0.074*
H22	0.8050	0.6383	0.5941	0.074*
C3A	0.76230 (14)	0.8342 (6)	0.55755 (14)	0.0609 (8)
C4A	0.78788 (14)	0.9980 (6)	0.57845 (15)	0.0629 (8)
H41	0.7953	0.9900	0.6203	0.075*
H42	0.7650	1.0947	0.5713	0.075*
C5A	0.83735 (15)	1.0350 (6)	0.54837 (16)	0.0661 (9)
H5A	0.8282	1.0650	0.5075	0.079*
C6A	0.86248 (17)	1.1946 (7)	0.5771 (2)	0.0791 (11)
H61	0.8882	1.2374	0.5524	0.095*
H62	0.8375	1.2854	0.5803	0.095*
C7A	0.88624 (14)	1.1545 (6)	0.63717 (18)	0.0648 (9)
C8A	0.92068 (12)	0.9967 (6)	0.64061 (15)	0.0550 (7)
H8A	0.9499	1.0227	0.6181	0.066*
C9A	0.89325 (12)	0.8367 (6)	0.61178 (13)	0.0504 (7)
H9A	0.8638	0.8147	0.6345	0.060*
C10A	0.87253 (13)	0.8750 (6)	0.54801 (14)	0.0602 (8)
C11A	0.92572 (13)	0.6740 (6)	0.61732 (13)	0.0555 (7)
H111	0.9543	0.6878	0.5933	0.067*
H112	0.9062	0.5759	0.6022	0.067*
C12A	0.94521 (11)	0.6337 (5)	0.68030 (13)	0.0497 (7)
H12A	0.9678	0.5332	0.6799	0.060*
C13A	0.97458 (11)	0.7899 (6)	0.70680 (13)	0.0507 (7)
C14A	0.93992 (12)	0.9514 (6)	0.70249 (14)	0.0520 (7)
H14A	0.9103	0.9240	0.7242	0.062*
C15A	0.97004 (13)	1.0877 (6)	0.73818 (17)	0.0652 (9)
H151	0.9480	1.1749	0.7533	0.078*
H152	0.9944	1.1444	0.7147	0.078*
C16A	0.99655 (14)	0.9827 (7)	0.78814 (18)	0.0704 (10)
H161	0.9826	1.0116	0.8251	0.084*
H162	1.0323	1.0089	0.7911	0.084*
C17A	0.98808 (12)	0.7875 (6)	0.77406 (14)	0.0553 (8)
H17A	0.9578	0.7510	0.7932	0.066*
C18A	1.02287 (13)	0.8153 (7)	0.67385 (16)	0.0645 (9)
H181	1.0142	0.8606	0.6355	0.077*
H182	1.0397	0.7057	0.6705	0.077*
H183	1.0448	0.8953	0.6950	0.077*
C19A	0.91518 (18)	0.9088 (9)	0.50690 (18)	0.0894 (14)
H191	0.9333	0.8030	0.5012	0.107*
H192	0.9377	0.9947	0.5239	0.107*
H193	0.9011	0.9500	0.4699	0.107*
C20A	1.03174 (13)	0.6706 (6)	0.79757 (16)	0.0620 (9)
H20A	1.0622	0.7058	0.7787	0.074*
C21A	1.02227 (16)	0.4806 (7)	0.7841 (2)	0.0789 (11)
H211	0.9890	0.4499	0.7944	0.095*
H212	1.0465	0.4111	0.8062	0.095*
H213	1.0253	0.4605	0.7431	0.095*
C22A	1.04146 (14)	0.6943 (8)	0.86397 (16)	0.0765 (12)
H221	1.0372	0.8158	0.8736	0.092*
H222	1.0166	0.6284	0.8839	0.092*
C23A	1.09407 (15)	0.6360 (8)	0.88655 (19)	0.0856 (13)
H231	1.0937	0.6200	0.9285	0.103*
H232	1.1006	0.5235	0.8696	0.103*
C24A	1.13695 (15)	0.7526 (8)	0.87483 (16)	0.0767 (12)
O25B	0.81557 (13)	0.1645 (6)	1.03524 (10)	0.0935 (10)
O29B	0.78136 (12)	0.1223 (5)	0.78345 (13)	0.0834 (9)
O26B	0.68402 (8)	0.6650	0.84201 (10)	0.0597 (6)
H26B	0.6839 (17)	0.698 (7)	0.876 (2)	0.087 (14)*
O27B	0.5588 (3)	0.907 (2)	0.5041 (5)	0.080 (4)	0.50
O28B	0.5156 (6)	0.842 (3)	0.5780 (6)	0.108 (7)	0.50
O27C	0.5576 (10)	0.844 (6)	0.5087 (11)	0.147 (14)	0.30
O28C	0.5165 (10)	0.912 (6)	0.5778 (10)	0.147 (16)	0.30
O27D	0.5345 (8)	0.7518 (19)	0.5468 (11)	0.072 (4)	0.20
O28D	0.5377 (8)	1.033 (2)	0.5364 (11)	0.089 (6)	0.20
C1B	0.83391 (14)	0.5449 (7)	0.95892 (13)	0.0662 (9)
H13	0.8666	0.5385	0.9801	0.079*
H14	0.8236	0.6657	0.9581	0.079*
C2B	0.79614 (16)	0.4410 (7)	0.99243 (14)	0.0710 (10)
H23	0.7966	0.4813	1.0326	0.085*
H24	0.7625	0.4584	0.9748	0.085*
C3B	0.80917 (14)	0.2522 (7)	0.99136 (14)	0.0661 (10)
C4B	0.81642 (14)	0.1795 (6)	0.93172 (13)	0.0631 (9)
H43	0.7841	0.1747	0.9098	0.076*
H44	0.8292	0.0618	0.9356	0.076*
C5B	0.85316 (13)	0.2885 (6)	0.89765 (13)	0.0570 (8)
H5B	0.8865	0.2780	0.9180	0.068*
C6B	0.85692 (14)	0.2117 (7)	0.83611 (14)	0.0651 (9)
H63	0.8841	0.2670	0.8168	0.078*
H64	0.8639	0.0883	0.8388	0.078*
C7B	0.80769 (14)	0.2416 (6)	0.80140 (13)	0.0584 (8)
C8B	0.79308 (12)	0.4295 (6)	0.79423 (12)	0.0476 (7)
H8B	0.8194	0.4891	0.7737	0.057*
C9B	0.79078 (11)	0.5117 (6)	0.85616 (11)	0.0458 (6)
H9B	0.7638	0.4515	0.8753	0.055*
C10B	0.83964 (12)	0.4836 (6)	0.89541 (13)	0.0547 (8)
C11B	0.77493 (11)	0.7039 (6)	0.85085 (13)	0.0493 (7)*
H113	0.7709	0.7494	0.8897	0.059*
H114	0.8018	0.7686	0.8341	0.059*
C12B	0.72641 (11)	0.7350 (6)	0.81368 (11)	0.0476 (6)
H12B	0.7216	0.8603	0.8088	0.057*
C13B	0.72889 (11)	0.6514 (5)	0.75274 (11)	0.0454 (6)
C14B	0.74245 (12)	0.4579 (5)	0.75987 (12)	0.0472 (7)
H14B	0.7164	0.4042	0.7824	0.057*
C15B	0.73579 (12)	0.3880 (6)	0.69761 (14)	0.0580 (8)*
H153	0.7292	0.2642	0.6976	0.070*
H154	0.7655	0.4103	0.6762	0.070*
C16B	0.68977 (14)	0.4896 (6)	0.67085 (14)	0.0615 (8)
H163	0.6608	0.4136	0.6658	0.074*
H164	0.6971	0.5365	0.6330	0.074*
C17B	0.67878 (12)	0.6396 (6)	0.71401 (12)	0.0504 (7)
H17B	0.6526	0.5988	0.7390	0.061*
C18B	0.76843 (11)	0.7501 (6)	0.71953 (13)	0.0514 (7)*
H184	0.8014	0.7271	0.7373	0.062*
H185	0.7617	0.8724	0.7210	0.062*
H186	0.7670	0.7125	0.6795	0.062*
C19B	0.88391 (13)	0.5870 (8)	0.87227 (18)	0.0772 (11)
H194	0.8780	0.7090	0.8770	0.093*
H195	0.8867	0.5615	0.8316	0.093*
H196	0.9146	0.5549	0.8938	0.093*
C20B	0.65890 (12)	0.8047 (6)	0.68308 (13)	0.0544 (7)
H20B	0.6848	0.8428	0.6572	0.065*
C21B	0.65027 (16)	0.9546 (7)	0.72504 (18)	0.0756 (11)
H214	0.6368	1.0524	0.7034	0.091*
H215	0.6817	0.9864	0.7450	0.091*
H216	0.6269	0.9190	0.7531	0.091*
C22B	0.61068 (13)	0.7674 (6)	0.64388 (14)	0.0613 (8)
H223	0.6141	0.6566	0.6244	0.074*
H224	0.5820	0.7599	0.6680	0.074*
C23B	0.60136 (13)	0.9091 (7)	0.59837 (16)	0.0681 (10)
H233	0.5982	1.0188	0.6186	0.082*
H234	0.6308	0.9171	0.5754	0.082*
C24B	0.55608 (13)	0.8864 (6)	0.55739 (14)	0.0571 (8)
O1	0.4479 (8)	0.672 (4)	0.0573 (9)	0.361 (10)*	0.70
O2	0.5000	0.909 (5)	0.0000	0.325 (14)*	0.60

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O25A	0.0679 (15)	0.094 (2)	0.0856 (17)	−0.0018 (16)	−0.0080 (12)	−0.0032 (17)
O29A	0.0932 (19)	0.0527 (14)	0.099 (2)	0.0052 (14)	−0.0075 (15)	−0.0146 (15)
O26A	0.0587 (12)	0.0521 (13)	0.0604 (13)	−0.0151 (12)	−0.0024 (10)	−0.0048 (11)
O27A	0.0689 (19)	0.149 (4)	0.187 (4)	−0.010 (2)	−0.021 (2)	0.080 (4)
O28A	0.0669 (16)	0.085 (2)	0.111 (2)	−0.0206 (16)	−0.0203 (15)	0.0204 (19)
C1A	0.078 (2)	0.072 (2)	0.0424 (15)	0.0096 (19)	−0.0069 (14)	−0.0061 (16)
C2A	0.075 (2)	0.059 (2)	0.0498 (16)	−0.0042 (18)	−0.0112 (14)	−0.0072 (16)
C3A	0.069 (2)	0.067 (2)	0.0457 (15)	0.0003 (18)	−0.0035 (13)	0.0016 (16)
C4A	0.072 (2)	0.057 (2)	0.0586 (18)	0.0088 (17)	−0.0070 (15)	0.0015 (16)
C5A	0.082 (2)	0.060 (2)	0.0553 (18)	0.0010 (19)	−0.0048 (16)	0.0150 (17)
C6A	0.088 (3)	0.053 (2)	0.094 (3)	−0.003 (2)	−0.006 (2)	0.020 (2)
C7A	0.067 (2)	0.0454 (18)	0.081 (2)	−0.0097 (16)	−0.0022 (17)	0.0031 (19)
C8A	0.0543 (17)	0.0470 (17)	0.0636 (18)	−0.0076 (14)	0.0026 (13)	0.0012 (15)
C9A	0.0566 (16)	0.0453 (16)	0.0489 (15)	−0.0035 (14)	0.0014 (12)	−0.0036 (13)
C10A	0.0687 (19)	0.064 (2)	0.0480 (15)	0.0006 (18)	0.0048 (14)	0.0065 (16)
C11A	0.0598 (17)	0.0541 (18)	0.0515 (16)	−0.0007 (15)	−0.0049 (13)	−0.0091 (15)
C12A	0.0519 (15)	0.0423 (16)	0.0544 (16)	−0.0039 (13)	−0.0026 (12)	−0.0057 (14)
C13A	0.0440 (14)	0.0526 (18)	0.0552 (16)	−0.0079 (13)	−0.0008 (12)	−0.0077 (14)
C14A	0.0519 (16)	0.0452 (16)	0.0585 (17)	−0.0075 (14)	−0.0003 (13)	−0.0056 (14)
C15A	0.0619 (19)	0.057 (2)	0.076 (2)	−0.0107 (17)	−0.0015 (16)	−0.0156 (18)
C16A	0.062 (2)	0.070 (2)	0.077 (2)	−0.0123 (19)	−0.0089 (17)	−0.022 (2)
C17A	0.0483 (15)	0.063 (2)	0.0544 (16)	−0.0133 (15)	−0.0029 (12)	−0.0083 (15)
C18A	0.0549 (17)	0.069 (2)	0.070 (2)	−0.0054 (17)	0.0091 (14)	−0.0024 (18)
C19A	0.097 (3)	0.114 (4)	0.060 (2)	0.000 (3)	0.0176 (19)	0.017 (2)
C20A	0.0522 (17)	0.065 (2)	0.0678 (19)	−0.0128 (17)	−0.0097 (14)	−0.0011 (18)
C21A	0.073 (2)	0.064 (2)	0.097 (3)	−0.008 (2)	−0.019 (2)	0.004 (2)
C22A	0.066 (2)	0.094 (3)	0.068 (2)	−0.027 (2)	−0.0110 (16)	0.010 (2)
C23A	0.083 (3)	0.094 (3)	0.076 (2)	−0.024 (2)	−0.0242 (19)	0.022 (2)
C24A	0.067 (2)	0.100 (3)	0.0610 (19)	−0.016 (2)	−0.0180 (16)	0.011 (2)
O25B	0.124 (2)	0.111 (3)	0.0462 (12)	0.006 (2)	0.0100 (13)	0.0242 (16)
O29B	0.118 (2)	0.0484 (15)	0.0805 (17)	−0.0013 (16)	−0.0200 (16)	−0.0053 (13)
O26B	0.0638 (13)	0.0738 (16)	0.0421 (11)	−0.0141 (12)	0.0073 (9)	−0.0101 (12)
O27B	0.041 (3)	0.148 (10)	0.052 (5)	−0.011 (5)	−0.002 (3)	0.024 (6)
O28B	0.067 (7)	0.188 (15)	0.069 (9)	−0.035 (8)	−0.004 (6)	0.064 (11)
O27C	0.124 (16)	0.24 (3)	0.075 (14)	0.072 (18)	0.012 (11)	−0.079 (18)
O28C	0.065 (12)	0.30 (4)	0.070 (15)	0.043 (18)	−0.009 (10)	−0.08 (2)
O27D	0.081 (10)	0.051 (8)	0.079 (11)	0.013 (7)	−0.025 (9)	−0.015 (8)
O28D	0.087 (11)	0.064 (9)	0.109 (13)	−0.012 (8)	−0.053 (11)	0.030 (10)
C1B	0.080 (2)	0.072 (2)	0.0438 (15)	−0.007 (2)	−0.0165 (14)	−0.0056 (16)
C2B	0.085 (2)	0.089 (3)	0.0392 (15)	0.005 (2)	0.0020 (15)	−0.0032 (17)
C3B	0.0657 (19)	0.089 (3)	0.0436 (15)	−0.006 (2)	0.0034 (13)	0.0104 (18)
C4B	0.081 (2)	0.064 (2)	0.0444 (15)	−0.0014 (19)	0.0014 (14)	0.0084 (16)
C5B	0.0577 (17)	0.069 (2)	0.0436 (15)	0.0041 (17)	−0.0015 (12)	0.0071 (15)
C6B	0.074 (2)	0.072 (2)	0.0490 (16)	0.0137 (19)	0.0038 (14)	0.0045 (16)
C7B	0.080 (2)	0.0560 (19)	0.0393 (14)	0.0049 (18)	0.0019 (13)	−0.0022 (15)
C8B	0.0558 (16)	0.0504 (17)	0.0363 (13)	−0.0063 (14)	0.0009 (11)	0.0009 (12)
C9B	0.0534 (15)	0.0497 (16)	0.0337 (12)	−0.0129 (13)	−0.0027 (10)	0.0007 (12)
C10B	0.0567 (17)	0.066 (2)	0.0408 (14)	−0.0133 (16)	−0.0063 (12)	0.0011 (14)
C12B	0.0572 (15)	0.0477 (16)	0.0379 (12)	−0.0091 (14)	0.0010 (11)	−0.0062 (12)
C13B	0.0542 (15)	0.0468 (16)	0.0347 (12)	−0.0061 (13)	−0.0012 (10)	−0.0035 (12)
C14B	0.0589 (16)	0.0452 (16)	0.0367 (13)	−0.0081 (14)	−0.0053 (11)	−0.0050 (12)
C16B	0.078 (2)	0.057 (2)	0.0468 (15)	−0.0037 (18)	−0.0125 (14)	−0.0087 (15)
C17B	0.0592 (16)	0.0516 (18)	0.0399 (13)	−0.0060 (14)	−0.0018 (12)	−0.0040 (13)
C19B	0.0590 (19)	0.096 (3)	0.075 (2)	−0.024 (2)	−0.0073 (16)	0.013 (2)
C20B	0.0559 (16)	0.0613 (19)	0.0454 (15)	0.0032 (16)	−0.0024 (12)	0.0003 (14)
C21B	0.083 (2)	0.070 (2)	0.071 (2)	0.013 (2)	−0.0159 (18)	−0.014 (2)
C22B	0.0645 (18)	0.067 (2)	0.0510 (16)	0.0007 (17)	−0.0082 (14)	−0.0007 (16)
C23B	0.0621 (19)	0.079 (3)	0.0616 (18)	0.0030 (19)	−0.0124 (15)	0.0070 (19)
C24B	0.0545 (18)	0.062 (2)	0.0546 (18)	0.0093 (18)	−0.0004 (14)	0.0035 (18)

Geometric parameters (Å, º) top

O25A—C3A	1.218 (4)	O27B—O28D	1.36 (3)
O29A—C7A	1.209 (5)	O27B—O27D	1.70 (3)
O26A—C12A	1.421 (4)	O28B—O28C	0.54 (5)
O26A—H26A	0.80 (4)	O28B—O27D	1.14 (2)
O27A—C24A	1.187 (5)	O28B—C24B	1.249 (13)
O28A—C24A	1.327 (6)	O27C—C24B	1.17 (2)
O28A—H28A	1.11 (5)	O27C—O27D	1.31 (4)
C1A—C2A	1.529 (5)	O27C—O28D	1.69 (3)
C1A—C10A	1.541 (5)	O28C—C24B	1.19 (2)
C1A—H11	0.9700	O28C—O28D	1.47 (4)
C1A—H12	0.9700	O28C—O27D	1.52 (3)
C2A—C3A	1.495 (5)	O27D—C24B	1.203 (15)
C2A—H21	0.9700	O28D—C24B	1.309 (16)
C2A—H22	0.9700	C1B—C2B	1.527 (6)
C3A—C4A	1.499 (6)	C1B—C10B	1.546 (4)
C4A—C5A	1.548 (5)	C1B—H13	0.9700
C4A—H41	0.9700	C1B—H14	0.9700
C4A—H42	0.9700	C2B—C3B	1.496 (7)
C5A—C6A	1.529 (6)	C2B—H23	0.9700
C5A—C10A	1.548 (5)	C2B—H24	0.9700
C5A—H5A	0.9800	C3B—C4B	1.500 (5)
C6A—C7A	1.513 (6)	C4B—C5B	1.536 (5)
C6A—H61	0.9700	C4B—H43	0.9700
C6A—H62	0.9700	C4B—H44	0.9700
C7A—C8A	1.522 (5)	C5B—C6B	1.538 (5)
C8A—C14A	1.519 (5)	C5B—C10B	1.546 (5)
C8A—C9A	1.559 (4)	C5B—H5B	0.9800
C8A—H8A	0.9800	C6B—C7B	1.509 (5)
C9A—C11A	1.523 (5)	C6B—H63	0.9700
C9A—C10A	1.559 (4)	C6B—H64	0.9700
C9A—H9A	0.9800	C7B—C8B	1.506 (5)
C10A—C19A	1.540 (5)	C8B—C14B	1.535 (4)
C11A—C12A	1.536 (4)	C8B—C9B	1.558 (4)
C11A—H111	0.9700	C8B—H8B	0.9800
C11A—H112	0.9700	C9B—C11B	1.542 (5)
C12A—C13A	1.540 (4)	C9B—C10B	1.551 (4)
C12A—H12A	0.9800	C9B—H9B	0.9800
C13A—C18A	1.541 (4)	C10B—C19B	1.542 (5)
C13A—C14A	1.549 (5)	C11B—C12B	1.522 (4)
C13A—C17A	1.562 (4)	C11B—H113	0.9700
C14A—C15A	1.528 (5)	C11B—H114	0.9700
C14A—H14A	0.9800	C12B—C13B	1.542 (4)
C15A—C16A	1.538 (6)	C12B—H12B	0.9800
C15A—H151	0.9700	C13B—C18B	1.536 (4)
C15A—H152	0.9700	C13B—C14B	1.540 (4)
C16A—C17A	1.551 (5)	C13B—C17B	1.560 (4)
C16A—H161	0.9700	C14B—C15B	1.525 (4)
C16A—H162	0.9700	C14B—H14B	0.9800
C17A—C20A	1.541 (5)	C15B—C16B	1.548 (5)
C17A—H17A	0.9800	C15B—H153	0.9700
C18A—H181	0.9600	C15B—H154	0.9700
C18A—H182	0.9600	C16B—C17B	1.560 (5)
C18A—H183	0.9600	C16B—H163	0.9700
C19A—H191	0.9600	C16B—H164	0.9700
C19A—H192	0.9600	C17B—C20B	1.535 (5)
C19A—H193	0.9600	C17B—H17B	0.9800
C20A—C21A	1.513 (6)	C18B—H184	0.9600
C20A—C22A	1.539 (5)	C18B—H185	0.9600
C20A—H20A	0.9800	C18B—H186	0.9600
C21A—H211	0.9600	C19B—H194	0.9600
C21A—H212	0.9600	C19B—H195	0.9600
C21A—H213	0.9600	C19B—H196	0.9600
C22A—C23A	1.530 (6)	C20B—C21B	1.528 (5)
C22A—H221	0.9700	C20B—C22B	1.548 (4)
C22A—H222	0.9700	C20B—H20B	0.9800
C23A—C24A	1.489 (6)	C21B—H214	0.9600
C23A—H231	0.9700	C21B—H215	0.9600
C23A—H232	0.9700	C21B—H216	0.9600
O25B—C3B	1.215 (5)	C22B—C23B	1.520 (5)
O29B—C7B	1.212 (5)	C22B—H223	0.9700
O26B—C12B	1.439 (4)	C22B—H224	0.9700
O26B—H26B	0.83 (5)	C23B—C24B	1.493 (4)
O27B—O27C	0.50 (5)	C23B—H233	0.9700
O27B—C24B	1.239 (11)	C23B—H234	0.9700

C12A—O26A—H26A	114 (3)	O27C—O27D—O28C	93 (2)
C24A—O28A—H28A	113 (3)	O28B—O27D—O27B	97.3 (13)
C2A—C1A—C10A	114.1 (3)	C24B—O27D—O27B	46.8 (10)
C2A—C1A—H11	108.7	O27C—O27D—O27B	12.0 (15)
C10A—C1A—H11	108.7	O28C—O27D—O27B	80.7 (18)
C2A—C1A—H12	108.7	C24B—O28D—O27B	55.3 (10)
C10A—C1A—H12	108.7	C24B—O28D—O28C	50.6 (12)
H11—C1A—H12	107.6	O27B—O28D—O28C	95.1 (16)
C3A—C2A—C1A	109.6 (3)	C24B—O28D—O27C	43.6 (11)
C3A—C2A—H21	109.7	O27B—O28D—O27C	14.5 (16)
C1A—C2A—H21	109.7	O28C—O28D—O27C	80.7 (17)
C3A—C2A—H22	109.7	C2B—C1B—C10B	114.7 (3)
C1A—C2A—H22	109.7	C2B—C1B—H13	108.6
H21—C2A—H22	108.2	C10B—C1B—H13	108.6
O25A—C3A—C2A	122.5 (4)	C2B—C1B—H14	108.6
O25A—C3A—C4A	121.3 (4)	C10B—C1B—H14	108.6
C2A—C3A—C4A	116.2 (3)	H13—C1B—H14	107.6
C3A—C4A—C5A	113.3 (3)	C3B—C2B—C1B	109.9 (3)
C3A—C4A—H41	108.9	C3B—C2B—H23	109.7
C5A—C4A—H41	108.9	C1B—C2B—H23	109.7
C3A—C4A—H42	108.9	C3B—C2B—H24	109.7
C5A—C4A—H42	108.9	C1B—C2B—H24	109.7
H41—C4A—H42	107.7	H23—C2B—H24	108.2
C6A—C5A—C4A	108.6 (3)	O25B—C3B—C2B	123.3 (4)
C6A—C5A—C10A	113.2 (3)	O25B—C3B—C4B	121.8 (4)
C4A—C5A—C10A	112.7 (3)	C2B—C3B—C4B	114.9 (3)
C6A—C5A—H5A	107.4	C3B—C4B—C5B	112.3 (3)
C4A—C5A—H5A	107.4	C3B—C4B—H43	109.2
C10A—C5A—H5A	107.4	C5B—C4B—H43	109.2
C7A—C6A—C5A	112.1 (3)	C3B—C4B—H44	109.2
C7A—C6A—H61	109.2	C5B—C4B—H44	109.2
C5A—C6A—H61	109.2	H43—C4B—H44	107.9
C7A—C6A—H62	109.2	C4B—C5B—C6B	109.5 (3)
C5A—C6A—H62	109.2	C4B—C5B—C10B	113.2 (3)
H61—C6A—H62	107.9	C6B—C5B—C10B	111.8 (3)
O29A—C7A—C6A	120.9 (4)	C4B—C5B—H5B	107.3
O29A—C7A—C8A	123.7 (3)	C6B—C5B—H5B	107.3
C6A—C7A—C8A	115.3 (3)	C10B—C5B—H5B	107.3
C14A—C8A—C7A	113.6 (3)	C7B—C6B—C5B	108.8 (3)
C14A—C8A—C9A	109.7 (3)	C7B—C6B—H63	109.9
C7A—C8A—C9A	110.2 (3)	C5B—C6B—H63	109.9
C14A—C8A—H8A	107.7	C7B—C6B—H64	109.9
C7A—C8A—H8A	107.7	C5B—C6B—H64	109.9
C9A—C8A—H8A	107.7	H63—C6B—H64	108.3
C11A—C9A—C10A	113.6 (3)	O29B—C7B—C8B	123.5 (3)
C11A—C9A—C8A	111.5 (2)	O29B—C7B—C6B	121.9 (4)
C10A—C9A—C8A	112.2 (3)	C8B—C7B—C6B	114.5 (3)
C11A—C9A—H9A	106.3	C7B—C8B—C14B	114.0 (3)
C10A—C9A—H9A	106.3	C7B—C8B—C9B	108.4 (2)
C8A—C9A—H9A	106.3	C14B—C8B—C9B	109.2 (2)
C19A—C10A—C1A	106.7 (3)	C7B—C8B—H8B	108.4
C19A—C10A—C5A	109.6 (3)	C14B—C8B—H8B	108.4
C1A—C10A—C5A	108.0 (3)	C9B—C8B—H8B	108.4
C19A—C10A—C9A	111.9 (3)	C11B—C9B—C10B	113.3 (3)
C1A—C10A—C9A	111.5 (3)	C11B—C9B—C8B	110.1 (2)
C5A—C10A—C9A	109.0 (3)	C10B—C9B—C8B	113.2 (3)
C9A—C11A—C12A	113.7 (3)	C11B—C9B—H9B	106.6
C9A—C11A—H111	108.8	C10B—C9B—H9B	106.6
C12A—C11A—H111	108.8	C8B—C9B—H9B	106.6
C9A—C11A—H112	108.8	C19B—C10B—C1B	106.6 (3)
C12A—C11A—H112	108.8	C19B—C10B—C5B	109.4 (3)
H111—C11A—H112	107.7	C1B—C10B—C5B	107.6 (3)
O26A—C12A—C11A	110.5 (2)	C19B—C10B—C9B	111.1 (3)
O26A—C12A—C13A	109.2 (2)	C1B—C10B—C9B	112.1 (3)
C11A—C12A—C13A	110.3 (3)	C5B—C10B—C9B	109.9 (3)
O26A—C12A—H12A	108.9	C12B—C11B—C9B	114.5 (2)
C11A—C12A—H12A	108.9	C12B—C11B—H113	108.6
C13A—C12A—H12A	108.9	C9B—C11B—H113	108.6
C12A—C13A—C18A	108.9 (3)	C12B—C11B—H114	108.6
C12A—C13A—C14A	108.5 (2)	C9B—C11B—H114	108.6
C18A—C13A—C14A	112.2 (3)	H113—C11B—H114	107.6
C12A—C13A—C17A	117.5 (3)	O26B—C12B—C11B	110.5 (2)
C18A—C13A—C17A	109.6 (2)	O26B—C12B—C13B	109.2 (2)
C14A—C13A—C17A	100.0 (3)	C11B—C12B—C13B	111.1 (2)
C8A—C14A—C15A	118.6 (3)	O26B—C12B—H12B	108.7
C8A—C14A—C13A	114.2 (3)	C11B—C12B—H12B	108.7
C15A—C14A—C13A	103.1 (3)	C13B—C12B—H12B	108.7
C8A—C14A—H14A	106.7	C18B—C13B—C14B	111.6 (3)
C15A—C14A—H14A	106.7	C18B—C13B—C12B	108.0 (2)
C13A—C14A—H14A	106.7	C14B—C13B—C12B	109.3 (2)
C14A—C15A—C16A	103.8 (3)	C18B—C13B—C17B	109.5 (2)
C14A—C15A—H151	111.0	C14B—C13B—C17B	101.0 (2)
C16A—C15A—H151	111.0	C12B—C13B—C17B	117.3 (2)
C14A—C15A—H152	111.0	C15B—C14B—C8B	118.6 (3)
C16A—C15A—H152	111.0	C15B—C14B—C13B	103.2 (2)
H151—C15A—H152	109.0	C8B—C14B—C13B	112.7 (2)
C15A—C16A—C17A	107.5 (3)	C15B—C14B—H14B	107.2
C15A—C16A—H161	110.2	C8B—C14B—H14B	107.2
C17A—C16A—H161	110.2	C13B—C14B—H14B	107.2
C15A—C16A—H162	110.2	C14B—C15B—C16B	103.7 (3)
C17A—C16A—H162	110.2	C14B—C15B—H153	111.0
H161—C16A—H162	108.5	C16B—C15B—H153	111.0
C20A—C17A—C16A	113.4 (3)	C14B—C15B—H154	111.0
C20A—C17A—C13A	118.4 (3)	C16B—C15B—H154	111.0
C16A—C17A—C13A	102.5 (3)	H153—C15B—H154	109.0
C20A—C17A—H17A	107.3	C15B—C16B—C17B	107.3 (2)
C16A—C17A—H17A	107.3	C15B—C16B—H163	110.3
C13A—C17A—H17A	107.3	C17B—C16B—H163	110.3
C13A—C18A—H181	109.5	C15B—C16B—H164	110.3
C13A—C18A—H182	109.5	C17B—C16B—H164	110.3
H181—C18A—H182	109.5	H163—C16B—H164	108.5
C13A—C18A—H183	109.5	C20B—C17B—C13B	118.3 (3)
H181—C18A—H183	109.5	C20B—C17B—C16B	113.2 (2)
H182—C18A—H183	109.5	C13B—C17B—C16B	102.6 (2)
C10A—C19A—H191	109.5	C20B—C17B—H17B	107.4
C10A—C19A—H192	109.5	C13B—C17B—H17B	107.4
H191—C19A—H192	109.5	C16B—C17B—H17B	107.4
C10A—C19A—H193	109.5	C13B—C18B—H184	109.5
H191—C19A—H193	109.5	C13B—C18B—H185	109.5
H192—C19A—H193	109.5	H184—C18B—H185	109.5
C21A—C20A—C22A	109.4 (4)	C13B—C18B—H186	109.5
C21A—C20A—C17A	112.4 (3)	H184—C18B—H186	109.5
C22A—C20A—C17A	110.8 (3)	H185—C18B—H186	109.5
C21A—C20A—H20A	108.0	C10B—C19B—H194	109.5
C22A—C20A—H20A	108.0	C10B—C19B—H195	109.5
C17A—C20A—H20A	108.0	H194—C19B—H195	109.5
C20A—C21A—H211	109.5	C10B—C19B—H196	109.5
C20A—C21A—H212	109.5	H194—C19B—H196	109.5
H211—C21A—H212	109.5	H195—C19B—H196	109.5
C20A—C21A—H213	109.5	C21B—C20B—C17B	113.3 (3)
H211—C21A—H213	109.5	C21B—C20B—C22B	110.8 (3)
H212—C21A—H213	109.5	C17B—C20B—C22B	111.4 (3)
C23A—C22A—C20A	113.3 (4)	C21B—C20B—H20B	107.0
C23A—C22A—H221	108.9	C17B—C20B—H20B	107.0
C20A—C22A—H221	108.9	C22B—C20B—H20B	107.0
C23A—C22A—H222	108.9	C20B—C21B—H214	109.5
C20A—C22A—H222	108.9	C20B—C21B—H215	109.5
H221—C22A—H222	107.7	H214—C21B—H215	109.5
C24A—C23A—C22A	117.2 (4)	C20B—C21B—H216	109.5
C24A—C23A—H231	108.0	H214—C21B—H216	109.5
C22A—C23A—H231	108.0	H215—C21B—H216	109.5
C24A—C23A—H232	108.0	C23B—C22B—C20B	111.1 (3)
C22A—C23A—H232	108.0	C23B—C22B—H223	109.4
H231—C23A—H232	107.2	C20B—C22B—H223	109.4
O27A—C24A—O28A	120.9 (4)	C23B—C22B—H224	109.4
O27A—C24A—C23A	125.0 (5)	C20B—C22B—H224	109.4
O28A—C24A—C23A	114.1 (3)	H223—C22B—H224	108.0
C12B—O26B—H26B	111 (3)	C24B—C23B—C22B	116.1 (3)
O27C—O27B—C24B	70 (3)	C24B—C23B—H233	108.3
O27C—O27B—O28D	123 (4)	C22B—C23B—H233	108.3
C24B—O27B—O28D	60.3 (9)	C24B—C23B—H234	108.3
O27C—O27B—O27D	33 (3)	C22B—C23B—H234	108.3
C24B—O27B—O27D	45.0 (7)	H233—C23B—H234	107.4
O28D—O27B—O27D	90.2 (10)	O27C—C24B—O28C	120.2 (17)
O28C—O28B—O27D	126 (4)	O27C—C24B—O27D	67 (2)
O28C—O28B—C24B	72 (4)	O28C—C24B—O27D	78.6 (19)
O27D—O28B—C24B	60.4 (12)	O27C—C24B—O27B	24 (2)
O27B—O27C—C24B	86 (4)	O28C—C24B—O27B	118.1 (14)
O27B—O27C—O27D	135 (4)	O27D—C24B—O27B	88.2 (14)
C24B—O27C—O27D	57.9 (14)	O27C—C24B—O28B	111.4 (19)
O27B—O27C—O28D	43 (3)	O28C—C24B—O28B	25 (2)
C24B—O27C—O28D	50.7 (12)	O27D—C24B—O28B	55.2 (13)
O27D—O27C—O28D	92.7 (14)	O27B—C24B—O28B	120.7 (8)
O28B—O28C—C24B	83 (4)	O27C—C24B—O28D	85.7 (19)
O28B—O28C—O28D	131 (4)	O28C—C24B—O28D	71.5 (19)
C24B—O28C—O28D	57.9 (14)	O27D—C24B—O28D	120.4 (8)
O28B—O28C—O27D	37 (3)	O27B—C24B—O28D	64.5 (13)
C24B—O28C—O27D	51.0 (12)	O28B—C24B—O28D	93.6 (13)
O28D—O28C—O27D	93.9 (17)	O27C—C24B—C23B	124.2 (12)
O28B—O27D—C24B	64.4 (10)	O28C—C24B—C23B	115.5 (12)
O28B—O27D—O27C	109.3 (18)	O27D—C24B—C23B	125.8 (7)
C24B—O27D—O27C	55.2 (14)	O27B—C24B—C23B	120.8 (5)
O28B—O27D—O28C	16.7 (15)	O28B—C24B—C23B	118.4 (7)
C24B—O27D—O28C	50.5 (13)	O28D—C24B—C23B	113.6 (7)

(V) top

Crystal data top

C₂₄H₃₄O₅	F(000) = 436
M_r = 402.51	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
a = 12.0863 (3) Å	Cell parameters from 3134 reflections
b = 6.8301 (2) Å	θ = 3.2–30.0°
c = 13.1153 (4) Å	µ = 0.09 mm⁻¹
β = 101.138 (1)°	T = 295 K
V = 1062.28 (5) Å³	Prism, colourless
Z = 2	0.40 × 0.26 × 0.12 mm

Data collection top

Nonius Kappa CCD diffractometer	2638 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 30.0°, θ_min = 3.2°
ϕ scans and ω scans	h = −17→17
16592 measured reflections	k = −9→8
3336 independent reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	All H-atom parameters refined
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0503P)² + 0.0934P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.008
3336 reflections	Δρ_max = 0.20 e Å⁻³
397 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.3 (12)

Crystal data top

C₂₄H₃₄O₅	V = 1062.28 (5) Å³
M_r = 402.51	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 12.0863 (3) Å	µ = 0.09 mm⁻¹
b = 6.8301 (2) Å	T = 295 K
c = 13.1153 (4) Å	0.40 × 0.26 × 0.12 mm
β = 101.138 (1)°

Data collection top

Nonius Kappa CCD diffractometer	2638 reflections with I > 2σ(I)
16592 measured reflections	R_int = 0.030
3336 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	All H-atom parameters refined
wR(F²) = 0.101	Δρ_max = 0.20 e Å⁻³
S = 1.05	Δρ_min = −0.15 e Å⁻³
3336 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
397 parameters	Absolute structure parameter: −0.3 (12)
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7791 (2)	0.2135	−0.21461 (16)	0.0480 (5)
C2	0.6780 (3)	0.0819 (5)	−0.25541 (19)	0.0615 (6)
C3	0.5747 (2)	0.2011 (6)	−0.29198 (17)	0.0592 (6)
C4	0.55089 (18)	0.3568 (5)	−0.21917 (17)	0.0512 (5)
C5	0.65509 (15)	0.4809 (5)	−0.17219 (14)	0.0369 (4)
C6	0.62475 (18)	0.6189 (5)	−0.08946 (15)	0.0421 (4)
C7	0.61213 (15)	0.5102 (5)	0.00811 (14)	0.0350 (4)
C8	0.71572 (14)	0.3918 (4)	0.05512 (12)	0.0291 (3)
C9	0.74277 (14)	0.2477 (4)	−0.02885 (12)	0.0282 (3)
C10	0.76095 (14)	0.3563 (5)	−0.12841 (13)	0.0323 (3)
C11	0.84169 (17)	0.1103 (5)	0.01662 (14)	0.0372 (4)
C12	0.82841 (15)	0.0220 (5)	0.11927 (13)	0.0324 (3)
C13	0.81672 (14)	0.1707 (4)	0.20229 (12)	0.0296 (3)
C14	0.70515 (14)	0.2804 (4)	0.15335 (12)	0.0300 (3)
C15	0.6758 (2)	0.3922 (5)	0.24512 (16)	0.0441 (5)
C16	0.7183 (2)	0.2608 (5)	0.34017 (16)	0.0492 (5)
C17	0.78585 (16)	0.0899 (5)	0.30341 (13)	0.0344 (4)
C18	0.91875 (17)	0.3092 (5)	0.22586 (16)	0.0403 (4)
C19	0.86450 (17)	0.4908 (5)	−0.10589 (18)	0.0466 (5)
C20	0.88291 (17)	0.0198 (5)	0.39006 (14)	0.0408 (4)
C21	0.9561 (2)	−0.1404 (6)	0.3549 (2)	0.0571 (6)
C22	0.8394 (2)	−0.0476 (5)	0.48764 (16)	0.0488 (5)
C23	0.7519 (3)	−0.2074 (6)	0.46712 (18)	0.0695 (9)
C24	0.7356 (2)	−0.3162 (5)	0.56145 (15)	0.0490 (5)
O25	0.51246 (19)	0.1696 (6)	−0.37494 (14)	0.0955 (8)
O26	0.81794 (15)	−0.1530 (4)	0.12880 (12)	0.0530 (4)
O27	0.80454 (15)	−0.3320 (5)	0.63925 (13)	0.0749 (6)
O28	0.63630 (17)	−0.4032 (6)	0.55638 (14)	0.0843 (7)
O29	0.52567 (12)	0.5113 (4)	0.04174 (12)	0.0543 (4)
H1A	0.847 (2)	0.133 (5)	−0.190 (2)	0.058 (7)*
H1B	0.791 (2)	0.292 (4)	−0.2795 (19)	0.051 (7)*
H2A	0.669 (3)	−0.008 (6)	−0.198 (3)	0.097 (11)*
H2B	0.701 (2)	−0.020 (5)	−0.311 (2)	0.077 (9)*
H4A	0.486 (3)	0.443 (5)	−0.255 (2)	0.078 (9)*
H4B	0.517 (2)	0.287 (4)	−0.160 (2)	0.059 (7)*
H5	0.674 (2)	0.565 (4)	−0.228 (2)	0.052 (7)*
H6A	0.687 (2)	0.714 (4)	−0.0687 (18)	0.051 (7)*
H6B	0.555 (2)	0.686 (4)	−0.1161 (18)	0.051 (7)*
H8	0.7743 (18)	0.487 (4)	0.0726 (17)	0.041 (6)*
H9	0.6744 (16)	0.162 (3)	−0.0447 (14)	0.027 (5)*
H11A	0.844 (2)	−0.002 (5)	−0.031 (2)	0.067 (8)*
H11B	0.915 (2)	0.185 (4)	0.0287 (18)	0.055 (7)*
H14	0.6462 (17)	0.180 (4)	0.1316 (16)	0.038 (5)*
H15A	0.712 (2)	0.517 (5)	0.251 (2)	0.061 (8)*
H15B	0.600 (3)	0.422 (5)	0.235 (2)	0.069 (8)*
H16A	0.766 (3)	0.336 (5)	0.395 (2)	0.072 (9)*
H16B	0.654 (3)	0.211 (5)	0.375 (2)	0.074 (9)*
H17	0.7377 (18)	−0.017 (4)	0.2845 (17)	0.037 (5)*
H18A	0.989 (2)	0.238 (5)	0.2595 (19)	0.055 (7)*
H18B	0.907 (2)	0.405 (4)	0.274 (2)	0.058 (7)*
H18C	0.932 (2)	0.374 (5)	0.168 (2)	0.059 (7)*
H19A	0.868 (2)	0.562 (5)	−0.166 (2)	0.066 (8)*
H19B	0.866 (2)	0.593 (5)	−0.043 (2)	0.063 (7)*
H19C	0.936 (2)	0.412 (5)	−0.089 (2)	0.063 (8)*
H20	0.932 (2)	0.131 (4)	0.4136 (18)	0.049 (6)*
H21A	0.903 (3)	−0.250 (7)	0.335 (3)	0.102 (12)*
H21B	0.993 (3)	−0.086 (5)	0.297 (3)	0.079 (9)*
H21C	1.015 (3)	−0.173 (7)	0.411 (3)	0.097 (11)*
H22A	0.906 (2)	−0.096 (4)	0.542 (2)	0.059 (7)*
H22B	0.809 (2)	0.055 (5)	0.515 (2)	0.058 (8)*
H23A	0.776 (5)	−0.310 (10)	0.417 (4)	0.16 (2)*
H23B	0.688 (3)	−0.185 (8)	0.425 (3)	0.109 (14)*
H28	0.597 (3)	−0.388 (7)	0.495 (3)	0.098 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0540 (12)	0.0582 (13)	0.0341 (9)	0.0068 (11)	0.0137 (9)	0.0010 (9)
C2	0.0892 (19)	0.0546 (13)	0.0405 (11)	−0.0082 (13)	0.0116 (12)	−0.0090 (11)
C3	0.0635 (14)	0.0680 (16)	0.0411 (11)	−0.0251 (13)	−0.0026 (10)	0.0044 (11)
C4	0.0343 (10)	0.0683 (15)	0.0462 (11)	−0.0047 (10)	−0.0044 (8)	0.0129 (11)
C5	0.0337 (9)	0.0437 (10)	0.0328 (9)	0.0003 (8)	0.0048 (7)	0.0119 (8)
C6	0.0421 (10)	0.0391 (10)	0.0446 (10)	0.0099 (9)	0.0075 (8)	0.0146 (9)
C7	0.0375 (9)	0.0314 (8)	0.0368 (8)	0.0080 (7)	0.0087 (7)	0.0055 (7)
C8	0.0306 (8)	0.0266 (7)	0.0297 (8)	0.0023 (6)	0.0048 (6)	0.0023 (6)
C9	0.0271 (8)	0.0307 (7)	0.0264 (7)	0.0015 (6)	0.0045 (6)	0.0027 (6)
C10	0.0277 (8)	0.0386 (9)	0.0304 (8)	−0.0015 (7)	0.0055 (6)	0.0060 (7)
C11	0.0413 (10)	0.0396 (9)	0.0314 (8)	0.0126 (8)	0.0089 (7)	0.0046 (8)
C12	0.0340 (9)	0.0309 (8)	0.0307 (8)	0.0054 (7)	0.0019 (6)	0.0005 (7)
C13	0.0320 (8)	0.0286 (7)	0.0265 (7)	0.0018 (6)	0.0012 (6)	0.0020 (6)
C14	0.0318 (8)	0.0301 (8)	0.0286 (7)	0.0035 (7)	0.0069 (6)	0.0025 (6)
C15	0.0567 (13)	0.0421 (11)	0.0355 (9)	0.0162 (10)	0.0139 (9)	0.0008 (8)
C16	0.0667 (14)	0.0503 (12)	0.0325 (9)	0.0144 (11)	0.0141 (9)	0.0025 (9)
C17	0.0415 (9)	0.0334 (8)	0.0272 (7)	−0.0015 (8)	0.0036 (7)	0.0022 (7)
C18	0.0400 (10)	0.0383 (10)	0.0396 (10)	−0.0061 (8)	0.0001 (8)	0.0036 (8)
C19	0.0345 (10)	0.0565 (13)	0.0488 (11)	−0.0097 (9)	0.0079 (8)	0.0128 (10)
C20	0.0482 (11)	0.0392 (9)	0.0306 (9)	−0.0046 (9)	−0.0033 (8)	0.0039 (8)
C21	0.0566 (14)	0.0618 (15)	0.0498 (13)	0.0174 (12)	0.0021 (11)	0.0143 (11)
C22	0.0681 (14)	0.0447 (11)	0.0299 (9)	−0.0083 (10)	−0.0002 (9)	0.0040 (8)
C23	0.097 (2)	0.0736 (19)	0.0331 (11)	−0.0384 (16)	−0.0005 (12)	0.0123 (11)
C24	0.0598 (13)	0.0516 (11)	0.0353 (9)	−0.0016 (10)	0.0081 (9)	0.0104 (9)
O25	0.0957 (15)	0.127 (2)	0.0502 (10)	−0.0371 (15)	−0.0195 (10)	−0.0068 (12)
O26	0.0842 (11)	0.0295 (7)	0.0438 (8)	0.0029 (7)	0.0083 (7)	−0.0007 (6)
O27	0.0646 (10)	0.1038 (16)	0.0502 (9)	−0.0076 (11)	−0.0041 (8)	0.0376 (10)
O28	0.0712 (12)	0.127 (2)	0.0493 (10)	−0.0294 (13)	−0.0013 (9)	0.0360 (12)
O29	0.0428 (8)	0.0616 (9)	0.0626 (9)	0.0185 (7)	0.0205 (7)	0.0207 (8)

Geometric parameters (Å, º) top

C1—C2	1.528 (4)	C13—C17	1.547 (2)
C1—C10	1.541 (3)	C13—C14	1.568 (2)
C1—H1A	0.99 (3)	C14—C15	1.524 (2)
C1—H1B	1.04 (2)	C14—H14	0.99 (2)
C2—C3	1.490 (4)	C15—C16	1.541 (3)
C2—H2A	1.00 (4)	C15—H15A	0.95 (3)
C2—H2B	1.09 (3)	C15—H15B	0.93 (3)
C3—O25	1.216 (3)	C16—C17	1.554 (3)
C3—C4	1.494 (4)	C16—H16A	0.98 (3)
C4—C5	1.544 (3)	C16—H16B	1.03 (3)
C4—H4A	1.02 (3)	C17—C20	1.543 (2)
C4—H4B	1.06 (3)	C17—H17	0.94 (3)
C5—C6	1.534 (3)	C18—H18A	1.00 (3)
C5—C10	1.551 (2)	C18—H18B	0.94 (3)
C5—H5	0.99 (3)	C18—H18C	0.92 (3)
C6—C7	1.512 (2)	C19—H19A	0.93 (3)
C6—H6A	0.99 (3)	C19—H19B	1.08 (3)
C6—H6B	0.96 (3)	C19—H19C	1.01 (3)
C7—O29	1.210 (2)	C20—C21	1.533 (3)
C7—C8	1.518 (2)	C20—C22	1.545 (3)
C8—C14	1.523 (2)	C20—H20	0.98 (3)
C8—C9	1.558 (2)	C21—H21A	0.99 (4)
C8—H8	0.96 (2)	C21—H21B	1.02 (3)
C9—C11	1.546 (2)	C21—H21C	0.95 (4)
C9—C10	1.554 (2)	C22—C23	1.507 (3)
C9—H9	1.00 (2)	C22—H22A	1.02 (3)
C10—C19	1.535 (3)	C22—H22B	0.90 (3)
C11—C12	1.512 (2)	C23—C24	1.489 (3)
C11—H11A	0.99 (3)	C23—H23A	1.04 (6)
C11—H11B	1.01 (3)	C23—H23B	0.88 (4)
C12—O26	1.211 (2)	C24—O27	1.191 (3)
C12—C13	1.516 (2)	C24—O28	1.329 (3)
C13—C18	1.537 (2)	O28—H28	0.86 (4)

C2—C1—C10	114.30 (17)	C18—C13—C14	112.43 (14)
C2—C1—H1A	110.3 (17)	C17—C13—C14	101.00 (13)
C10—C1—H1A	109.4 (16)	C8—C14—C15	119.23 (14)
C2—C1—H1B	104.3 (14)	C8—C14—C13	112.28 (13)
C10—C1—H1B	109.8 (14)	C15—C14—C13	103.23 (14)
H1A—C1—H1B	108.5 (19)	C8—C14—H14	106.0 (12)
C3—C2—C1	110.8 (2)	C15—C14—H14	108.1 (12)
C3—C2—H2A	112 (2)	C13—C14—H14	107.6 (13)
C1—C2—H2A	107 (2)	C14—C15—C16	104.79 (15)
C3—C2—H2B	116.0 (16)	C14—C15—H15A	110.1 (17)
C1—C2—H2B	108.9 (16)	C16—C15—H15A	112.2 (17)
H2A—C2—H2B	101 (3)	C14—C15—H15B	111.9 (19)
O25—C3—C2	121.7 (3)	C16—C15—H15B	114.4 (18)
O25—C3—C4	122.4 (3)	H15A—C15—H15B	104 (3)
C2—C3—C4	115.83 (19)	C15—C16—C17	107.41 (15)
C3—C4—C5	113.77 (18)	C15—C16—H16A	110 (2)
C3—C4—H4A	109.9 (18)	C17—C16—H16A	110 (2)
C5—C4—H4A	111.0 (19)	C15—C16—H16B	112.7 (18)
C3—C4—H4B	107.6 (15)	C17—C16—H16B	112.1 (19)
C5—C4—H4B	110.7 (14)	H16A—C16—H16B	104 (2)
H4A—C4—H4B	103 (2)	C20—C17—C13	117.84 (15)
C6—C5—C4	109.37 (16)	C20—C17—C16	112.02 (16)
C6—C5—C10	111.59 (15)	C13—C17—C16	103.06 (15)
C4—C5—C10	113.42 (17)	C20—C17—H17	107.4 (14)
C6—C5—H5	106.5 (15)	C13—C17—H17	107.0 (13)
C4—C5—H5	108.2 (15)	C16—C17—H17	109.3 (13)
C10—C5—H5	107.5 (14)	C13—C18—H18A	111.6 (17)
C7—C6—C5	111.94 (16)	C13—C18—H18B	110.2 (16)
C7—C6—H6A	106.5 (14)	H18A—C18—H18B	105 (2)
C5—C6—H6A	108.8 (14)	C13—C18—H18C	112.7 (18)
C7—C6—H6B	108.5 (14)	H18A—C18—H18C	110 (2)
C5—C6—H6B	110.3 (14)	H18B—C18—H18C	107 (2)
H6A—C6—H6B	111 (2)	C10—C19—H19A	108.1 (18)
O29—C7—C6	122.72 (16)	C10—C19—H19B	115.1 (14)
O29—C7—C8	123.91 (16)	H19A—C19—H19B	108 (2)
C6—C7—C8	113.28 (14)	C10—C19—H19C	111.1 (17)
C7—C8—C14	114.37 (13)	H19A—C19—H19C	107 (2)
C7—C8—C9	108.59 (13)	H19B—C19—H19C	107 (2)
C14—C8—C9	110.22 (13)	C21—C20—C17	113.62 (17)
C7—C8—H8	104.4 (14)	C21—C20—C22	110.19 (19)
C14—C8—H8	108.4 (13)	C17—C20—C22	111.74 (17)
C9—C8—H8	110.7 (13)	C21—C20—H20	107.3 (14)
C11—C9—C10	112.92 (13)	C17—C20—H20	108.7 (15)
C11—C9—C8	111.28 (13)	C22—C20—H20	104.8 (13)
C10—C9—C8	112.04 (14)	C20—C21—H21A	104 (2)
C11—C9—H9	105.8 (12)	C20—C21—H21B	108.8 (19)
C10—C9—H9	110.5 (11)	H21A—C21—H21B	116 (3)
C8—C9—H9	103.7 (11)	C20—C21—H21C	109 (2)
C19—C10—C1	107.09 (16)	H21A—C21—H21C	112 (3)
C19—C10—C5	109.06 (16)	H21B—C21—H21C	107 (3)
C1—C10—C5	107.45 (15)	C23—C22—C20	114.04 (18)
C19—C10—C9	111.50 (15)	C23—C22—H22A	108.7 (17)
C1—C10—C9	112.19 (16)	C20—C22—H22A	108.8 (14)
C5—C10—C9	109.42 (13)	C23—C22—H22B	107.9 (18)
C12—C11—C9	112.24 (14)	C20—C22—H22B	109.5 (18)
C12—C11—H11A	105.7 (18)	H22A—C22—H22B	108 (2)
C9—C11—H11A	109.9 (17)	C24—C23—C22	114.5 (2)
C12—C11—H11B	107.7 (14)	C24—C23—H23A	107 (3)
C9—C11—H11B	110.2 (16)	C22—C23—H23A	109 (3)
H11A—C11—H11B	111 (2)	C24—C23—H23B	111 (3)
O26—C12—C11	121.13 (17)	C22—C23—H23B	119 (3)
O26—C12—C13	124.15 (17)	H23A—C23—H23B	93 (4)
C11—C12—C13	114.39 (15)	O27—C24—O28	118.6 (2)
C12—C13—C18	111.98 (15)	O27—C24—C23	125.0 (2)
C12—C13—C17	116.61 (14)	O28—C24—C23	116.4 (2)
C18—C13—C17	111.36 (14)	C24—O28—H28	109 (3)
C12—C13—C14	102.61 (12)

Experimental details

	(I)	(II)	(III)	(IV-alpha)
Crystal data
Chemical formula	C₂₄H₃₈O₅	C₂₄H₃₈O₅	C₂₄H₃₆O₅	C₂₄H₃₆O₅
M_r	406.54	406.54	404.53	404.53
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Orthorhombic, P2₁2₁2₁	Monoclinic, P2₁	Orthorhombic, P2₁2₁2₁
Temperature (K)	295	295	295	295
a, b, c (Å)	8.9879 (1), 9.4028 (1), 26.4369 (4)	6.3122 (1), 10.8884 (2), 32.0624 (7)	10.2677 (4), 7.1108 (2), 15.2270 (6)	8.4953 (1), 12.7060 (2), 20.8011 (3)
α, β, γ (°)	90, 90, 90	90, 90, 90	90, 92.340 (1), 90	90, 90, 90
V (Å³)	2234.22 (5)	2203.64 (7)	1110.82 (7)	2245.30 (5)
Z	4	4	2	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.08	0.08	0.08	0.08
Crystal size (mm)	0.42 × 0.35 × 0.28	0.36 × 0.14 × 0.10	0.25 × 0.11 × 0.06	0.45 × 0.35 × 0.32

Data collection
Diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24241, 3049, 2385	13705, 3006, 2415	14953, 2721, 2236	26164, 3664, 3189
R_int	0.041	0.076	0.039	0.035
(sin θ/λ)_max (Å⁻¹)	0.661	0.661	0.650	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.04	0.044, 0.120, 1.04	0.041, 0.107, 1.05	0.050, 0.146, 1.06
No. of reflections	3049	3006	2721	3664
No. of parameters	277	277	273	406
No. of restraints	0	0	1	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13	0.16, −0.16	0.15, −0.14	0.45, −0.32
Absolute structure	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter	−3.4 (15)	1.2 (15)	0.2 (14)	−0.3 (15)

	(IV-beta)	(V)
Crystal data
Chemical formula	C₂₄H₃₆O₅·1/2(H₂O)	C₂₄H₃₄O₅
M_r	413.54	402.51
Crystal system, space group	Monoclinic, C2	Monoclinic, P2₁
Temperature (K)	295	295
a, b, c (Å)	26.6049 (4), 7.7044 (1), 22.9126 (3)	12.0863 (3), 6.8301 (2), 13.1153 (4)
α, β, γ (°)	90, 93.424 (1), 90	90, 101.138 (1), 90
V (Å³)	4688.1 (1)	1062.28 (5)
Z	8	2
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.08	0.09
Crystal size (mm)	0.35 × 0.12 × 0.08	0.40 × 0.26 × 0.12

Data collection
Diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26846, 5683, 4381	16592, 3336, 2638
R_int	0.034	0.030
(sin θ/λ)_max (Å⁻¹)	0.650	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.166, 1.01	0.038, 0.101, 1.05
No. of reflections	5683	3336
No. of parameters	567	397
No. of restraints	0	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.27	0.20, −0.15
Absolute structure	Flack H D (1983), Acta Cryst. A39, 876-881	Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter	1.6 (15)	−0.3 (12)

Computer programs: Kappa-CCD server software (Nonius, 1997), DENZO SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), ORTEP III (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 1999).

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		Medline
		CIF
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		Plain Text