Diiso­propyl 2-(2-benzoyl-1-phenyl­ethyl)­malonate

Jeyabharathi, A.; Ponnuswamy, M.N.; Narasimhan, S.; Velmathi, S.

doi:10.1107/S1600536802000739

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Diisopropyl 2-(2-benzoyl-1-phenylethyl)malonate

A. Jeyabharathi, M. N. Ponnuswamy, S. Narasimhan and S. Velmathi

In the title compound, C₂₄H₂₈O₅, the keto group is planar. Weak C—H

O hydrogen bonds play a significant role in the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000739/ci6092sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000739/ci6092Isup2.hkl Contains datablock I

CCDC reference: 182640

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.047
wR factor = 0.142
Data-to-parameter ratio = 16.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

A number of compounds derived from chalcones possess multi-protecting biochemical activities, such as antifungal, antimalarial, antifertility etc. The biological activity of these compounds depends on the conformation of the keto group present in the molecule. Chalcones and their derivatives showed inhibitory action against S. aureus, F. graminearum and B. alli (Marrian et al., 1947). These compounds were also toxic to red spider mite (Eaton & Davis, 1950).

In the title molecule, (I), the bond distances are found to agree with the literature values (Allen et al., 1987). The bond angles at phenyl rings A and B show no significant deviations from the standard value, except around atoms C14 and C19. The slight distortion in the exocyclic bond angles at C14 and C19 may be due to the steric interactions between the isopropyl groups and phenyl rings. The dihedral angle between phenyl rings A and B is 83.8 (2)° and they are oriented at angles of 8.7 (1) and 87.0 (1)°, respectively, with respect to the keto group. The O5—C5—C4—C3 torsion angle of -17.7 (3)° shows that the molecule assumes an s-cis conformation for the keto system. Apart from van der Waals interactions, the packing of the molecules in the crystal is stabilized by intermolecular C—H···O interactions (Desiraju, 1991, 1996).

Experimental top

To 1 mmol of LiAlH₄ in dry tetrahydrofuran (THF), 1 mmol of amine ester was added at room temperature in a dried side arm flask and stirred for 4 h. To the stirred solution, benzalacetophenol (5 mmol) and diisopropyl malonate (5 mmol) were added and stirring continued for 7 h. The reaction was monitored through by thin-layer chromatography (TLC) until all the diisopropyl malonate had reacted. The reaction was quenched with 1 N HCl and extracted with ethyl acetate. The combined organic layer was washed with NaHCO₃ and dried over anhydrous Na₂SO₄. Removal of the solvent under reduced pressure gave a syrupy mass which on flash column chromotography yielded a crystalline solid. Colourless needle-shaped crystals were obtained by slow evaporation at room temperature from a hexane–ethyl acetate (1:1) mixture.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SDP (Frenz, 1978); data reduction: XCAD4-PC (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1994); software used to prepare material for publication: PARST97 (Nardelli, 1983, 1995).

Figures top

Fig. 1. A view of the title compound showing the atom-numbering scheme and 30% probability ellipsoids.

Diisopropyl 2-(2-benzoyl-1-phenylethyl)malonate top

Crystal data top

C₂₄H₂₈O₅	Z = 2
M_r = 396.46	F(000) = 424
Triclinic, P1	D_x = 1.194 Mg m⁻³
a = 6.031 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.2147 (10) Å	Cell parameters from 25 reflections
c = 19.0691 (10) Å	θ = 14–25°
α = 74.759 (10)°	µ = 0.67 mm⁻¹
β = 89.109 (10)°	T = 293 K
γ = 76.871 (10)°	Needle, colourless
V = 1102.6 (2) Å³	0.20 × 0.20 × 0.15 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.019
Radiation source: fine-focus sealed tube	θ_max = 71.9°, θ_min = 2.4°
Graphite monochromator	h = −7→6
ω–2θ scans	k = 0→12
4453 measured reflections	l = −22→23
4204 independent reflections	3 standard reflections every 200 reflections
2392 reflections with I > 2σ(I)	intensity decay: <0.1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0623P)² + 0.1575P] where P = (F_o² + 2F_c²)/3
4204 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₄H₂₈O₅	γ = 76.871 (10)°
M_r = 396.46	V = 1102.6 (2) Å³
Triclinic, P1	Z = 2
a = 6.031 (1) Å	Cu Kα radiation
b = 10.2147 (10) Å	µ = 0.67 mm⁻¹
c = 19.0691 (10) Å	T = 293 K
α = 74.759 (10)°	0.20 × 0.20 × 0.15 mm
β = 89.109 (10)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.019
4453 measured reflections	3 standard reflections every 200 reflections
4204 independent reflections	intensity decay: <0.1%
2392 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
4204 reflections	Δρ_min = −0.19 e Å⁻³
262 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	1.1347 (3)	0.99829 (18)	0.11925 (9)	0.0603 (5)
O2	0.8924 (3)	0.85727 (16)	0.14735 (8)	0.0498 (4)
O3	0.9619 (3)	0.72998 (18)	0.33566 (10)	0.0708 (5)
O4	1.2720 (3)	0.71594 (17)	0.26996 (9)	0.0612 (5)
O5	0.3666 (3)	1.0893 (2)	0.32229 (9)	0.0678 (5)
C1	1.0267 (4)	0.9340 (2)	0.16284 (12)	0.0453 (5)
C2	1.0144 (4)	0.9325 (2)	0.24265 (11)	0.0434 (5)
H2	1.1293	0.9791	0.2538	0.052*
C3	0.7781 (4)	1.0154 (2)	0.25679 (11)	0.0438 (5)
H3	0.6654	0.9622	0.2522	0.053*
C4	0.7707 (4)	1.0356 (2)	0.33383 (12)	0.0505 (6)
H4A	0.8335	0.9465	0.3683	0.061*
H4B	0.8667	1.0983	0.3370	0.061*
C5	0.5342 (4)	1.0934 (2)	0.35513 (12)	0.0495 (6)
C6	0.8644 (4)	0.8568 (2)	0.07126 (12)	0.0498 (6)
H6	0.8623	0.9498	0.0397	0.060*
C7	0.6369 (4)	0.8245 (3)	0.06518 (15)	0.0726 (8)
H7A	0.5207	0.8950	0.0776	0.109*
H7B	0.6363	0.7353	0.0978	0.109*
H7C	0.6076	0.8225	0.0162	0.109*
C8	1.0562 (5)	0.7526 (3)	0.05194 (15)	0.0682 (8)
H8A	1.1973	0.7787	0.0565	0.102*
H8B	1.0316	0.7501	0.0027	0.102*
H8C	1.0626	0.6620	0.0842	0.102*
C9	1.0739 (4)	0.7826 (2)	0.28881 (12)	0.0481 (6)
C10	1.3455 (5)	0.5647 (3)	0.30186 (14)	0.0623 (7)
H10	1.2971	0.5401	0.3520	0.075*
C11	1.2404 (5)	0.4933 (3)	0.25669 (18)	0.0815 (9)
H11A	1.0776	0.5173	0.2592	0.122*
H11B	1.2952	0.3942	0.2748	0.122*
H11C	1.2809	0.5226	0.2071	0.122*
C12	1.6006 (5)	0.5312 (3)	0.30115 (19)	0.0898 (10)
H12A	1.6600	0.5783	0.3313	0.135*
H12B	1.6465	0.5614	0.2522	0.135*
H12C	1.6586	0.4324	0.3195	0.135*
C13	0.2943 (5)	1.2238 (3)	0.43224 (15)	0.0730 (8)
H13	0.1695	1.2311	0.4022	0.088*
C14	0.5086 (4)	1.1553 (2)	0.41831 (12)	0.0515 (6)
C15	0.6900 (5)	1.1460 (3)	0.46398 (13)	0.0712 (8)
H15	0.8357	1.1007	0.4553	0.085*
C16	0.6576 (7)	1.2028 (4)	0.52233 (16)	0.0993 (12)
H16	0.7808	1.1946	0.5532	0.119*
C17	0.4462 (9)	1.2707 (4)	0.5348 (2)	0.1137 (14)
H17	0.4258	1.3101	0.5739	0.136*
C18	0.2642 (7)	1.2818 (4)	0.4909 (2)	0.0998 (12)
H18	0.1197	1.3282	0.5000	0.120*
C19	0.7147 (4)	1.1552 (2)	0.20032 (11)	0.0434 (5)
C20	0.5228 (4)	1.1911 (3)	0.15454 (12)	0.0542 (6)
H20	0.4301	1.1285	0.1581	0.065*
C21	0.7953 (5)	1.3780 (3)	0.14160 (15)	0.0673 (7)
H21	0.8891	1.4402	0.1371	0.081*
C22	0.4669 (5)	1.3196 (3)	0.10332 (14)	0.0668 (7)
H22	0.3367	1.3426	0.0730	0.080*
C23	0.6019 (6)	1.4130 (3)	0.09706 (14)	0.0703 (8)
H23	0.5631	1.4993	0.0630	0.084*
C24	0.8504 (4)	1.2505 (2)	0.19298 (13)	0.0560 (6)
H24	0.9808	1.2283	0.2232	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0678 (12)	0.0673 (11)	0.0595 (10)	−0.0329 (9)	0.0244 (9)	−0.0271 (9)
O2	0.0608 (10)	0.0542 (9)	0.0437 (8)	−0.0233 (8)	0.0098 (7)	−0.0211 (7)
O3	0.0829 (13)	0.0552 (11)	0.0681 (11)	−0.0086 (9)	0.0303 (10)	−0.0135 (9)
O4	0.0597 (11)	0.0500 (10)	0.0694 (11)	−0.0009 (8)	0.0139 (8)	−0.0189 (8)
O5	0.0520 (11)	0.0942 (14)	0.0661 (11)	−0.0141 (10)	0.0056 (9)	−0.0391 (10)
C1	0.0458 (13)	0.0424 (12)	0.0524 (13)	−0.0095 (10)	0.0100 (10)	−0.0218 (10)
C2	0.0451 (13)	0.0429 (12)	0.0466 (12)	−0.0091 (10)	0.0050 (10)	−0.0206 (10)
C3	0.0440 (13)	0.0466 (13)	0.0449 (12)	−0.0092 (10)	0.0050 (9)	−0.0205 (10)
C4	0.0521 (14)	0.0558 (14)	0.0436 (12)	−0.0038 (11)	0.0037 (10)	−0.0209 (11)
C5	0.0542 (15)	0.0511 (14)	0.0431 (12)	−0.0091 (11)	0.0062 (11)	−0.0152 (10)
C6	0.0570 (15)	0.0549 (14)	0.0419 (12)	−0.0149 (11)	0.0063 (10)	−0.0188 (11)
C7	0.0564 (17)	0.099 (2)	0.0750 (18)	−0.0210 (15)	0.0021 (13)	−0.0429 (17)
C8	0.0620 (17)	0.0801 (19)	0.0716 (17)	−0.0124 (14)	0.0113 (13)	−0.0397 (15)
C9	0.0507 (15)	0.0491 (13)	0.0474 (13)	−0.0069 (11)	0.0048 (11)	−0.0221 (11)
C10	0.0671 (18)	0.0471 (14)	0.0642 (16)	0.0045 (12)	0.0020 (13)	−0.0151 (12)
C11	0.084 (2)	0.0638 (18)	0.098 (2)	−0.0071 (16)	−0.0090 (17)	−0.0312 (17)
C12	0.070 (2)	0.078 (2)	0.117 (3)	0.0085 (16)	−0.0106 (18)	−0.0402 (19)
C13	0.0732 (19)	0.081 (2)	0.0711 (18)	−0.0156 (15)	0.0262 (15)	−0.0341 (16)
C14	0.0624 (16)	0.0524 (14)	0.0420 (12)	−0.0135 (12)	0.0146 (11)	−0.0170 (10)
C15	0.082 (2)	0.088 (2)	0.0495 (15)	−0.0171 (16)	0.0063 (14)	−0.0293 (14)
C16	0.120 (3)	0.138 (3)	0.0642 (19)	−0.044 (3)	0.0171 (19)	−0.058 (2)
C17	0.151 (4)	0.141 (3)	0.086 (3)	−0.058 (3)	0.047 (3)	−0.077 (3)
C18	0.103 (3)	0.114 (3)	0.102 (3)	−0.024 (2)	0.052 (2)	−0.065 (2)
C19	0.0477 (13)	0.0442 (12)	0.0420 (11)	−0.0068 (10)	0.0061 (10)	−0.0215 (10)
C20	0.0539 (15)	0.0637 (16)	0.0500 (13)	−0.0124 (12)	−0.0012 (11)	−0.0247 (12)
C21	0.084 (2)	0.0521 (16)	0.0703 (17)	−0.0202 (14)	0.0109 (15)	−0.0210 (14)
C22	0.0750 (19)	0.0680 (18)	0.0516 (15)	0.0002 (15)	−0.0112 (13)	−0.0191 (14)
C23	0.102 (2)	0.0504 (16)	0.0524 (15)	−0.0064 (16)	0.0014 (15)	−0.0124 (12)
C24	0.0610 (16)	0.0497 (14)	0.0611 (15)	−0.0126 (12)	−0.0007 (12)	−0.0211 (12)

Geometric parameters (Å, º) top

O1—C1	1.199 (2)	C10—H10	0.98
O2—C1	1.333 (3)	C11—H11A	0.96
O2—C6	1.465 (2)	C11—H11B	0.96
O3—C9	1.199 (3)	C11—H11C	0.96
O4—C9	1.329 (3)	C12—H12A	0.96
O4—C10	1.468 (3)	C12—H12B	0.96
O5—C5	1.212 (3)	C12—H12C	0.96
C1—C2	1.518 (3)	C13—C14	1.381 (3)
C2—C9	1.516 (3)	C13—C18	1.388 (4)
C2—C3	1.543 (3)	C13—H13	0.93
C2—H2	0.98	C14—C15	1.379 (4)
C3—C19	1.517 (3)	C15—C16	1.376 (4)
C3—C4	1.535 (3)	C15—H15	0.93
C3—H3	0.98	C16—C17	1.356 (5)
C4—C5	1.508 (3)	C16—H16	0.93
C4—H4A	0.97	C17—C18	1.358 (5)
C4—H4B	0.97	C17—H17	0.93
C5—C14	1.492 (3)	C18—H18	0.93
C6—C7	1.495 (3)	C19—C20	1.381 (3)
C6—C8	1.497 (3)	C19—C24	1.387 (3)
C6—H6	0.98	C20—C22	1.388 (3)
C7—H7A	0.96	C20—H20	0.93
C7—H7B	0.96	C21—C23	1.375 (4)
C7—H7C	0.96	C21—C24	1.381 (3)
C8—H8A	0.96	C21—H21	0.93
C8—H8B	0.96	C22—C23	1.370 (4)
C8—H8C	0.96	C22—H22	0.93
C10—C11	1.495 (4)	C23—H23	0.93
C10—C12	1.499 (4)	C24—H24	0.93

C1—O2—C6	118.08 (17)	C11—C10—H10	110.0
C9—O4—C10	118.15 (19)	C12—C10—H10	110.0
O1—C1—O2	124.5 (2)	C10—C11—H11A	109.5
O1—C1—C2	125.4 (2)	C10—C11—H11B	109.5
O2—C1—C2	110.00 (19)	H11A—C11—H11B	109.5
C9—C2—C1	109.10 (17)	C10—C11—H11C	109.5
C9—C2—C3	113.61 (18)	H11A—C11—H11C	109.5
C1—C2—C3	109.88 (17)	H11B—C11—H11C	109.5
C9—C2—H2	108.0	C10—C12—H12A	109.5
C1—C2—H2	108.0	C10—C12—H12B	109.5
C3—C2—H2	108.0	H12A—C12—H12B	109.5
C19—C3—C4	110.56 (17)	C10—C12—H12C	109.5
C19—C3—C2	110.29 (18)	H12A—C12—H12C	109.5
C4—C3—C2	111.50 (18)	H12B—C12—H12C	109.5
C19—C3—H3	108.1	C14—C13—C18	120.3 (3)
C4—C3—H3	108.1	C14—C13—H13	119.8
C2—C3—H3	108.1	C18—C13—H13	119.8
C5—C4—C3	113.60 (19)	C15—C14—C13	118.4 (2)
C5—C4—H4A	108.8	C15—C14—C5	122.8 (2)
C3—C4—H4A	108.8	C13—C14—C5	118.8 (2)
C5—C4—H4B	108.8	C16—C15—C14	120.7 (3)
C3—C4—H4B	108.8	C16—C15—H15	119.6
H4A—C4—H4B	107.7	C14—C15—H15	119.6
O5—C5—C14	120.0 (2)	C17—C16—C15	120.0 (3)
O5—C5—C4	121.2 (2)	C17—C16—H16	120.0
C14—C5—C4	118.8 (2)	C15—C16—H16	120.0
O2—C6—C7	105.17 (18)	C16—C17—C18	120.7 (3)
O2—C6—C8	110.43 (19)	C16—C17—H17	119.7
C7—C6—C8	113.1 (2)	C18—C17—H17	119.7
O2—C6—H6	109.3	C17—C18—C13	119.8 (3)
C7—C6—H6	109.3	C17—C18—H18	120.1
C8—C6—H6	109.3	C13—C18—H18	120.1
C6—C7—H7A	109.5	C20—C19—C24	118.1 (2)
C6—C7—H7B	109.5	C20—C19—C3	121.4 (2)
H7A—C7—H7B	109.5	C24—C19—C3	120.5 (2)
C6—C7—H7C	109.5	C19—C20—C22	120.7 (2)
H7A—C7—H7C	109.5	C19—C20—H20	119.7
H7B—C7—H7C	109.5	C22—C20—H20	119.7
C6—C8—H8A	109.5	C23—C21—C24	120.1 (3)
C6—C8—H8B	109.5	C23—C21—H21	119.9
H8A—C8—H8B	109.5	C24—C21—H21	119.9
C6—C8—H8C	109.5	C23—C22—C20	120.5 (3)
H8A—C8—H8C	109.5	C23—C22—H22	119.7
H8B—C8—H8C	109.5	C20—C22—H22	119.7
O3—C9—O4	124.1 (2)	C22—C23—C21	119.5 (3)
O3—C9—C2	126.0 (2)	C22—C23—H23	120.3
O4—C9—C2	109.9 (2)	C21—C23—H23	120.3
O4—C10—C11	108.4 (2)	C21—C24—C19	121.1 (2)
O4—C10—C12	105.6 (2)	C21—C24—H24	119.4
C11—C10—C12	112.6 (2)	C19—C24—H24	119.4
O4—C10—H10	110.0

C6—O2—C1—O1	−3.4 (3)	C18—C13—C14—C15	0.2 (4)
C6—O2—C1—C2	174.27 (17)	C18—C13—C14—C5	179.6 (3)
O1—C1—C2—C9	−126.9 (2)	O5—C5—C14—C15	170.8 (3)
O2—C1—C2—C9	55.4 (2)	C4—C5—C14—C15	−8.7 (3)
O1—C1—C2—C3	107.9 (3)	O5—C5—C14—C13	−8.6 (4)
O2—C1—C2—C3	−69.7 (2)	C4—C5—C14—C13	172.0 (2)
C9—C2—C3—C19	−170.52 (17)	C13—C14—C15—C16	0.4 (4)
C1—C2—C3—C19	−48.0 (2)	C5—C14—C15—C16	−178.9 (3)
C9—C2—C3—C4	66.2 (2)	C14—C15—C16—C17	−1.0 (5)
C1—C2—C3—C4	−171.23 (19)	C15—C16—C17—C18	1.0 (6)
C19—C3—C4—C5	67.0 (3)	C16—C17—C18—C13	−0.4 (6)
C2—C3—C4—C5	−169.87 (19)	C14—C13—C18—C17	−0.2 (5)
C3—C4—C5—O5	17.7 (3)	C4—C3—C19—C20	−116.6 (2)
C3—C4—C5—C14	−162.9 (2)	C2—C3—C19—C20	119.7 (2)
C1—O2—C6—C7	−153.7 (2)	C4—C3—C19—C24	64.0 (3)
C1—O2—C6—C8	84.0 (2)	C2—C3—C19—C24	−59.8 (2)
C10—O4—C9—O3	7.9 (3)	C24—C19—C20—C22	−0.7 (3)
C10—O4—C9—C2	−172.30 (19)	C3—C19—C20—C22	179.8 (2)
C1—C2—C9—O3	−127.4 (3)	C19—C20—C22—C23	0.3 (4)
C3—C2—C9—O3	−4.4 (3)	C20—C22—C23—C21	0.6 (4)
C1—C2—C9—O4	52.8 (2)	C24—C21—C23—C22	−1.1 (4)
C3—C2—C9—O4	175.78 (17)	C23—C21—C24—C19	0.7 (4)
C9—O4—C10—C11	85.3 (3)	C20—C19—C24—C21	0.2 (3)
C9—O4—C10—C12	−153.8 (2)	C3—C19—C24—C21	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱ	0.98	2.57	3.509 (3)	161
C4—H4A···O3	0.97	2.41	3.063 (3)	124
C7—H7A···O1ⁱⁱ	0.96	2.54	3.437 (3)	156

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈O₅
M_r	396.46
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.031 (1), 10.2147 (10), 19.0691 (10)
α, β, γ (°)	74.759 (10), 89.109 (10), 76.871 (10)
V (Å³)	1102.6 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4453, 4204, 2392
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.142, 1.01
No. of reflections	4204
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), SDP (Frenz, 1978), XCAD4-PC (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1994), PARST97 (Nardelli, 1983, 1995).

Selected geometric parameters (Å, º) top

O1—C1	1.199 (2)	C2—C3	1.543 (3)
O2—C1	1.333 (3)	C3—C19	1.517 (3)
O2—C6	1.465 (2)	C3—C4	1.535 (3)
O3—C9	1.199 (3)	C4—C5	1.508 (3)
O4—C9	1.329 (3)	C5—C14	1.492 (3)
O5—C5	1.212 (3)

C14—C5—C4	118.8 (2)	C15—C14—C13	118.4 (2)
C7—C6—C8	113.1 (2)	C20—C19—C24	118.1 (2)
C11—C10—C12	112.6 (2)

C9—C2—C3—C19	−170.52 (17)	C3—C4—C5—O5	17.7 (3)
C1—C2—C3—C19	−48.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱ	0.98	2.57	3.509 (3)	161.4
C4—H4A···O3	0.97	2.41	3.063 (3)	124.3
C7—H7A···O1ⁱⁱ	0.96	2.54	3.437 (3)	156.4

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

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