Diethyl 2-(triphenyl­meth­yl)malonate

Yuan, X.-Y.; Zhang, M.; Ng, S.W.

doi:10.1107/S1600536808018163

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1314

doi:10.1107/S1600536808018163

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Diethyl 2-(triphenylmethyl)malonate

Xian-You Yuan,^a Min Zhang ^a and Seik Weng Ng ^b ^*

^aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou 425100, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 May 2008; accepted 15 June 2008; online 21 June 2008)

In the title compound, C₂₆H₂₆O₄, steric crowding of the Ph₃C– group with the –CH(CO₂Et)₂ unit leads to a long C—C bond [1.585 (2) Å]. One of the two ethyl groups is disordered over two sites in a 60:40 ratio.

Related literature

For the synthesis by direct reaction of trityl chloride with diethyl malonate, see: Patai et al. (1962 ). For the medicinal use of the compound, see: Brugnara et al. (2000 ); Lencer et al. (2002 ). For a related crystal structure, 3-(triphenylmethyl)-2,4-pentadione, see: Sykora et al. (2007 ).

Experimental

Crystal data

C₂₆H₂₆O₄
M_r = 402.47
Monoclinic, P 2₁ /c
a = 8.5871 (5) Å
b = 19.884 (1) Å
c = 12.7591 (8) Å
β = 97.302 (1)°
V = 2160.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 (2) K
0.48 × 0.45 × 0.40 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: none
12570 measured reflections
4693 independent reflections
2761 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.150
S = 1.00
4693 reflections
290 parameters
28 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018163/bt2717sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018163/bt2717Isup2.hkl

checkCIF report

Comment top

The title compound can be synthesized by triturating triphenylmethyl chloride with diethyl malonate, which is an active methylene compound (Patai et al., 1962). The compound belongs to a class of triarylmethane derivatives that have been patented for the treatment of diarrhoea (Lencer et al., 2002) as well as for sickle-cell anemia (Brugnara et al., 2000). The compound (Scheme I, Fig. 1) features crowding of the Ph₃C– portion with the –CH(CO₂Et)₂ portion, which leads to a long carbon-carbon bond [1.585 (2) Å]. The distance is similar to that [1.587 (3) Å] found in 3-(triphenylmethyl)-2,4-pentadione (Sykora et al., 2007).

Related literature top

For the synthesis by direct reaction of trityl chloride with diethyl malonate, see: Patai et al. (1962). For the medicinal use of the compound, see: Brugnara et al. (2000); Lencer et al. (2002). For a related crystal structure, 3-(triphenylmethyl)-2,4-pentadione, see: Sykora et al. (2007).

Experimental top

To a solution of diethyl malonate (1.15 g, 7.18 mmol) in anhydrous ethanol (6 ml) was added powdered magnesium (0.18 g, 7.4 mmol) along with several drops of carbon tetrachloride and a granule of iodine. After the reaction has abated, the mixture was heated until the magnesium had dissolved completely. The solvent was allowed to evaporate. The solid material was ground with benzene (4 ml). The solvent was again evaporated. The residue was redissolved in benzene (4 ml), and to the solution was added triphenylmethyl chloride (2 g, 7.18 mmol) in benzene (4 ml). The mixture was stirred for five hours until it turned pale green. 10% Hydrochloric acid was added to dissolve the precipitate of magnesium hydroxide. The solution was extracted twice with benzene (4 ml). The combined organic portions were washed twice with water (5 ml) before being dried over an anhydrous salt. The solvent benzene was evaporated and the product recrystallized from acetone to afford colorless crystals (yield 75%); m.p. 411–412 K.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The minor disorder component of the ethyl group is not shown.

Diethyl 2-(triphenylmethyl)malonate top

Crystal data top

C₂₆H₂₆O₄	F(000) = 856
M_r = 402.47	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3695 reflections
a = 8.5871 (5) Å	θ = 2.6–27.1°
b = 19.884 (1) Å	µ = 0.08 mm⁻¹
c = 12.7591 (8) Å	T = 295 K
β = 97.302 (1)°	Block, colorless
V = 2160.9 (2) Å³	0.48 × 0.45 × 0.40 mm
Z = 4

Data collection top

Bruker SMART 1000 diffractometer	2761 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 27.1°, θ_min = 1.9°
ϕ and ω scans	h = −8→11
12570 measured reflections	k = −25→25
4693 independent reflections	l = −16→15

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0735P)² + 0.2019P] where P = (F_o² + 2F_c²)/3
4693 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.26 e Å⁻³
28 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₆H₂₆O₄	V = 2160.9 (2) Å³
M_r = 402.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5871 (5) Å	µ = 0.08 mm⁻¹
b = 19.884 (1) Å	T = 295 K
c = 12.7591 (8) Å	0.48 × 0.45 × 0.40 mm
β = 97.302 (1)°

Data collection top

Bruker SMART 1000 diffractometer	2761 reflections with I > 2σ(I)
12570 measured reflections	R_int = 0.045
4693 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	28 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
4693 reflections	Δρ_min = −0.22 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.53297 (19)	0.54974 (7)	0.74906 (12)	0.0649 (4)
O2	0.64769 (19)	0.50922 (8)	0.61546 (13)	0.0669 (5)
O4	0.24156 (16)	0.46954 (7)	0.79704 (10)	0.0502 (4)
O3	0.19910 (17)	0.51697 (8)	0.63787 (11)	0.0613 (4)
C1	0.4903 (2)	0.38239 (8)	0.71672 (13)	0.0358 (4)
C2	0.6123 (2)	0.39784 (8)	0.81297 (13)	0.0359 (4)
C3	0.7724 (2)	0.39498 (10)	0.80592 (15)	0.0449 (5)
H3	0.8065	0.3808	0.7432	0.054*
C4	0.8819 (2)	0.41277 (11)	0.89050 (17)	0.0557 (5)
H4	0.9885	0.4104	0.8842	0.067*
C5	0.8340 (3)	0.43394 (10)	0.98370 (17)	0.0567 (6)
H5	0.9076	0.4454	1.0408	0.068*
C6	0.6760 (3)	0.43800 (10)	0.99189 (15)	0.0495 (5)
H6	0.6428	0.4524	1.0547	0.059*
C7	0.5668 (2)	0.42082 (9)	0.90763 (14)	0.0425 (4)
H7	0.4605	0.4246	0.9141	0.051*
C8	0.5680 (2)	0.33995 (9)	0.63526 (14)	0.0395 (4)
C9	0.6181 (2)	0.27544 (9)	0.66570 (16)	0.0495 (5)
H9	0.6047	0.2602	0.7329	0.059*
C10	0.6866 (3)	0.23381 (11)	0.5992 (2)	0.0590 (6)
H10	0.7203	0.1912	0.6220	0.071*
C11	0.7059 (3)	0.25471 (12)	0.49889 (19)	0.0624 (6)
H11	0.7513	0.2264	0.4534	0.075*
C12	0.6575 (3)	0.31736 (13)	0.46735 (18)	0.0620 (6)
H12	0.6697	0.3318	0.3995	0.074*
C13	0.5898 (2)	0.36049 (11)	0.53507 (15)	0.0520 (5)
H13	0.5591	0.4035	0.5123	0.062*
C14	0.3499 (2)	0.33914 (9)	0.74171 (14)	0.0388 (4)
C15	0.3452 (2)	0.30478 (9)	0.83520 (16)	0.0480 (5)
H15	0.4302	0.3075	0.8881	0.058*
C16	0.2164 (3)	0.26641 (11)	0.8516 (2)	0.0628 (6)
H16	0.2153	0.2439	0.9154	0.075*
C17	0.0903 (3)	0.26130 (12)	0.7744 (2)	0.0677 (7)
H17	0.0027	0.2363	0.7863	0.081*
C18	0.0944 (3)	0.29331 (11)	0.6800 (2)	0.0657 (6)
H18	0.0101	0.2895	0.6269	0.079*
C19	0.2231 (2)	0.33111 (10)	0.66349 (17)	0.0522 (5)
H19	0.2253	0.3518	0.5983	0.063*
C20	0.4235 (2)	0.45117 (9)	0.66689 (14)	0.0381 (4)
H20	0.3912	0.4426	0.5916	0.046*
C21	0.5482 (2)	0.50592 (9)	0.67315 (15)	0.0436 (5)
C22	0.2799 (2)	0.47852 (9)	0.71124 (15)	0.0401 (4)
C23	0.6698 (11)	0.5959 (4)	0.7676 (7)	0.072 (2)	0.60 (1)
H23A	0.6579	0.6324	0.7169	0.087*	0.60 (1)
H23B	0.7657	0.5718	0.7592	0.087*	0.60 (1)
C23'	0.6178 (13)	0.6129 (4)	0.7620 (10)	0.068 (3)	0.40 (1)
H23C	0.5493	0.6492	0.7782	0.082*	0.40 (1)
H23D	0.6640	0.6243	0.6988	0.082*	0.40 (1)
C24	0.6779 (11)	0.6230 (4)	0.8771 (4)	0.079 (2)	0.60 (1)
H24A	0.7610	0.6554	0.8888	0.118*	0.60 (1)
H24B	0.6979	0.5869	0.9269	0.118*	0.60 (1)
H24C	0.5799	0.6441	0.8861	0.118*	0.60 (1)
C24'	0.7417 (13)	0.5995 (6)	0.8527 (9)	0.079 (3)	0.40 (1)
H24D	0.8071	0.6386	0.8656	0.118*	0.40 (1)
H24E	0.8045	0.5620	0.8362	0.118*	0.40 (1)
H24F	0.6932	0.5895	0.9146	0.118*	0.40 (1)
C25	0.0595 (3)	0.54963 (15)	0.6682 (2)	0.0814 (8)
H25A	−0.0127	0.5161	0.6889	0.098*
H25B	0.0885	0.5793	0.7278	0.098*
C26	−0.0156 (3)	0.58803 (13)	0.5784 (2)	0.0773 (8)
H26A	−0.1078	0.6097	0.5975	0.116*
H26B	−0.0446	0.5583	0.5199	0.116*
H26C	0.0562	0.6214	0.5587	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0754 (11)	0.0514 (8)	0.0723 (10)	−0.0232 (8)	0.0262 (8)	−0.0127 (8)
O2	0.0595 (10)	0.0647 (10)	0.0821 (11)	−0.0104 (8)	0.0309 (9)	0.0031 (8)
O4	0.0437 (8)	0.0608 (9)	0.0471 (8)	0.0084 (6)	0.0096 (6)	0.0015 (6)
O3	0.0503 (9)	0.0776 (10)	0.0582 (9)	0.0294 (8)	0.0153 (7)	0.0177 (8)
C1	0.0308 (9)	0.0362 (9)	0.0399 (9)	0.0017 (7)	0.0028 (8)	0.0010 (7)
C2	0.0347 (10)	0.0307 (9)	0.0415 (10)	0.0007 (7)	0.0021 (8)	0.0036 (7)
C3	0.0365 (11)	0.0484 (11)	0.0495 (11)	−0.0053 (8)	0.0042 (9)	−0.0005 (9)
C4	0.0347 (11)	0.0638 (14)	0.0659 (14)	−0.0108 (10)	−0.0040 (10)	0.0004 (11)
C5	0.0565 (14)	0.0555 (13)	0.0535 (13)	−0.0110 (10)	−0.0113 (11)	−0.0013 (10)
C6	0.0590 (14)	0.0432 (11)	0.0448 (11)	−0.0002 (9)	0.0005 (10)	−0.0040 (9)
C7	0.0415 (11)	0.0397 (10)	0.0455 (10)	0.0051 (8)	0.0024 (9)	0.0015 (8)
C8	0.0308 (10)	0.0426 (10)	0.0439 (10)	−0.0025 (8)	−0.0001 (8)	−0.0066 (8)
C9	0.0451 (12)	0.0433 (11)	0.0595 (12)	0.0028 (9)	0.0039 (10)	−0.0058 (9)
C10	0.0479 (13)	0.0451 (12)	0.0829 (16)	0.0016 (10)	0.0045 (12)	−0.0185 (11)
C11	0.0435 (13)	0.0681 (16)	0.0755 (16)	−0.0016 (11)	0.0067 (11)	−0.0355 (13)
C12	0.0566 (14)	0.0766 (17)	0.0544 (13)	0.0005 (12)	0.0132 (11)	−0.0159 (12)
C13	0.0504 (13)	0.0555 (12)	0.0507 (12)	0.0050 (10)	0.0092 (10)	−0.0037 (10)
C14	0.0316 (10)	0.0362 (9)	0.0485 (11)	0.0021 (8)	0.0046 (8)	−0.0013 (8)
C15	0.0428 (11)	0.0437 (11)	0.0571 (12)	−0.0020 (9)	0.0044 (9)	0.0063 (9)
C16	0.0600 (15)	0.0523 (13)	0.0791 (15)	−0.0059 (11)	0.0201 (13)	0.0121 (11)
C17	0.0432 (13)	0.0574 (14)	0.1040 (19)	−0.0133 (10)	0.0153 (13)	0.0043 (13)
C18	0.0425 (13)	0.0626 (14)	0.0887 (17)	−0.0090 (10)	−0.0048 (12)	−0.0025 (13)
C19	0.0412 (12)	0.0524 (12)	0.0604 (12)	−0.0061 (9)	−0.0035 (10)	0.0011 (10)
C20	0.0358 (10)	0.0407 (10)	0.0379 (9)	0.0033 (8)	0.0053 (8)	0.0021 (8)
C21	0.0420 (11)	0.0397 (10)	0.0493 (11)	0.0052 (8)	0.0064 (9)	0.0112 (9)
C22	0.0339 (10)	0.0401 (10)	0.0457 (11)	0.0027 (8)	0.0027 (8)	0.0022 (8)
C23	0.073 (4)	0.058 (4)	0.089 (4)	−0.030 (3)	0.020 (4)	−0.011 (3)
C23'	0.071 (6)	0.042 (4)	0.092 (6)	−0.006 (4)	0.018 (4)	0.004 (4)
C24	0.084 (4)	0.068 (4)	0.090 (4)	−0.025 (3)	0.029 (3)	−0.022 (3)
C24'	0.070 (5)	0.075 (5)	0.091 (6)	−0.024 (4)	0.010 (5)	−0.005 (4)
C25	0.0613 (16)	0.108 (2)	0.0788 (17)	0.0450 (15)	0.0224 (14)	0.0225 (15)
C26	0.0531 (15)	0.0748 (16)	0.104 (2)	0.0225 (12)	0.0098 (14)	0.0167 (14)

Geometric parameters (Å, º) top

O2—C21	1.198 (2)	C14—C15	1.380 (3)
O1—C21	1.321 (2)	C14—C19	1.390 (3)
O1—C23'	1.451 (8)	C15—C16	1.381 (3)
O1—C23	1.486 (6)	C15—H15	0.9300
O4—C22	1.196 (2)	C16—C17	1.372 (3)
O3—C22	1.333 (2)	C16—H16	0.9300
O3—C25	1.459 (3)	C17—C18	1.367 (3)
C1—C2	1.540 (2)	C17—H17	0.9300
C1—C14	1.547 (2)	C18—C19	1.374 (3)
C1—C8	1.554 (2)	C18—H18	0.9300
C1—C20	1.585 (2)	C19—H19	0.9300
C2—C3	1.390 (3)	C20—C22	1.521 (2)
C2—C7	1.393 (2)	C20—C21	1.522 (3)
C3—C4	1.384 (3)	C20—H20	0.9800
C3—H3	0.9300	C23—C24	1.491 (7)
C4—C5	1.373 (3)	C23—H23A	0.9700
C4—H4	0.9300	C23—H23B	0.9700
C5—C6	1.376 (3)	C23'—C24'	1.492 (9)
C5—H5	0.9300	C23'—H23C	0.9700
C6—C7	1.377 (3)	C23'—H23D	0.9700
C6—H6	0.9300	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C13	1.377 (3)	C24—H24C	0.9600
C8—C9	1.392 (3)	C24'—H24D	0.9600
C9—C10	1.370 (3)	C24'—H24E	0.9600
C9—H9	0.9300	C24'—H24F	0.9600
C10—C11	1.376 (3)	C25—C26	1.456 (3)
C10—H10	0.9300	C25—H25A	0.9700
C11—C12	1.358 (3)	C25—H25B	0.9700
C11—H11	0.9300	C26—H26A	0.9600
C12—C13	1.396 (3)	C26—H26B	0.9600
C12—H12	0.9300	C26—H26C	0.9600
C13—H13	0.9300

C21—O1—C23'	124.0 (6)	C16—C17—H17	120.3
C21—O1—C23	112.0 (3)	C17—C18—C19	120.1 (2)
C22—O3—C25	116.18 (16)	C17—C18—H18	119.9
C2—C1—C14	114.55 (14)	C19—C18—H18	119.9
C2—C1—C8	109.59 (14)	C18—C19—C14	121.6 (2)
C14—C1—C8	104.36 (13)	C18—C19—H19	119.2
C2—C1—C20	108.83 (13)	C14—C19—H19	119.2
C14—C1—C20	108.08 (14)	C22—C20—C21	108.85 (15)
C8—C1—C20	111.40 (14)	C22—C20—C1	115.39 (14)
C3—C2—C7	117.29 (17)	C21—C20—C1	112.30 (14)
C3—C2—C1	121.21 (15)	C22—C20—H20	106.6
C7—C2—C1	121.27 (15)	C21—C20—H20	106.6
C4—C3—C2	121.24 (18)	C1—C20—H20	106.6
C4—C3—H3	119.4	O2—C21—O1	123.98 (19)
C2—C3—H3	119.4	O2—C21—C20	123.97 (18)
C5—C4—C3	120.32 (19)	O1—C21—C20	112.05 (16)
C5—C4—H4	119.8	O4—C22—O3	123.32 (17)
C3—C4—H4	119.8	O4—C22—C20	128.13 (17)
C4—C5—C6	119.38 (19)	O3—C22—C20	108.54 (15)
C4—C5—H5	120.3	O1—C23—C24	108.3 (5)
C6—C5—H5	120.3	O1—C23—H23A	110.0
C5—C6—C7	120.44 (19)	C24—C23—H23A	110.0
C5—C6—H6	119.8	O1—C23—H23B	110.0
C7—C6—H6	119.8	C24—C23—H23B	110.0
C6—C7—C2	121.30 (18)	H23A—C23—H23B	108.4
C6—C7—H7	119.3	O1—C23'—C24'	103.5 (7)
C2—C7—H7	119.3	O1—C23'—H23C	111.1
C13—C8—C9	117.30 (17)	C24'—C23'—H23C	111.1
C13—C8—C1	125.47 (17)	O1—C23'—H23D	111.1
C9—C8—C1	117.22 (16)	C24'—C23'—H23D	111.1
C10—C9—C8	121.7 (2)	H23C—C23'—H23D	109.0
C10—C9—H9	119.1	C23—C24—H24A	109.5
C8—C9—H9	119.1	C23—C24—H24B	109.5
C9—C10—C11	120.4 (2)	H24A—C24—H24B	109.5
C9—C10—H10	119.8	C23—C24—H24C	109.5
C11—C10—H10	119.8	H24A—C24—H24C	109.5
C12—C11—C10	119.0 (2)	H24B—C24—H24C	109.5
C12—C11—H11	120.5	C23'—C24'—H24D	109.5
C10—C11—H11	120.5	C23'—C24'—H24E	109.5
C11—C12—C13	121.1 (2)	H24D—C24'—H24E	109.5
C11—C12—H12	119.5	C23'—C24'—H24F	109.5
C13—C12—H12	119.5	H24D—C24'—H24F	109.5
C8—C13—C12	120.6 (2)	H24E—C24'—H24F	109.5
C8—C13—H13	119.7	C26—C25—O3	108.75 (19)
C12—C13—H13	119.7	C26—C25—H25A	109.9
C15—C14—C19	117.23 (18)	O3—C25—H25A	109.9
C15—C14—C1	124.25 (16)	C26—C25—H25B	109.9
C19—C14—C1	118.43 (16)	O3—C25—H25B	109.9
C14—C15—C16	121.1 (2)	H25A—C25—H25B	108.3
C14—C15—H15	119.5	C25—C26—H26A	109.5
C16—C15—H15	119.5	C25—C26—H26B	109.5
C17—C16—C15	120.5 (2)	H26A—C26—H26B	109.5
C17—C16—H16	119.8	C25—C26—H26C	109.5
C15—C16—H16	119.8	H26A—C26—H26C	109.5
C18—C17—C16	119.4 (2)	H26B—C26—H26C	109.5
C18—C17—H17	120.3

C14—C1—C2—C3	138.03 (17)	C19—C14—C15—C16	−2.7 (3)
C8—C1—C2—C3	21.2 (2)	C1—C14—C15—C16	−179.21 (18)
C20—C1—C2—C3	−100.89 (18)	C14—C15—C16—C17	0.4 (3)
C14—C1—C2—C7	−47.6 (2)	C15—C16—C17—C18	1.5 (4)
C8—C1—C2—C7	−164.48 (15)	C16—C17—C18—C19	−1.0 (4)
C20—C1—C2—C7	73.48 (19)	C17—C18—C19—C14	−1.4 (3)
C7—C2—C3—C4	1.5 (3)	C15—C14—C19—C18	3.2 (3)
C1—C2—C3—C4	176.05 (17)	C1—C14—C19—C18	179.89 (18)
C2—C3—C4—C5	−0.2 (3)	C2—C1—C20—C22	−89.67 (18)
C3—C4—C5—C6	−0.7 (3)	C14—C1—C20—C22	35.3 (2)
C4—C5—C6—C7	0.2 (3)	C8—C1—C20—C22	149.39 (15)
C5—C6—C7—C2	1.2 (3)	C2—C1—C20—C21	35.86 (19)
C3—C2—C7—C6	−2.0 (3)	C14—C1—C20—C21	160.83 (14)
C1—C2—C7—C6	−176.55 (16)	C8—C1—C20—C21	−85.08 (18)
C2—C1—C8—C13	−115.26 (19)	C23'—O1—C21—O2	10.1 (5)
C14—C1—C8—C13	121.62 (19)	C23—O1—C21—O2	−10.6 (6)
C20—C1—C8—C13	5.2 (2)	C23'—O1—C21—C20	−169.3 (5)
C2—C1—C8—C9	65.5 (2)	C23—O1—C21—C20	170.0 (5)
C14—C1—C8—C9	−57.6 (2)	C22—C20—C21—O2	−153.65 (19)
C20—C1—C8—C9	−173.96 (16)	C1—C20—C21—O2	77.3 (2)
C13—C8—C9—C10	0.1 (3)	C22—C20—C21—O1	25.7 (2)
C1—C8—C9—C10	179.37 (17)	C1—C20—C21—O1	−103.29 (17)
C8—C9—C10—C11	−0.9 (3)	C25—O3—C22—O4	1.2 (3)
C9—C10—C11—C12	0.7 (3)	C25—O3—C22—C20	−177.88 (19)
C10—C11—C12—C13	0.3 (3)	C21—C20—C22—O4	−100.3 (2)
C9—C8—C13—C12	0.9 (3)	C1—C20—C22—O4	27.0 (3)
C1—C8—C13—C12	−178.32 (18)	C21—C20—C22—O3	78.69 (19)
C11—C12—C13—C8	−1.1 (3)	C1—C20—C22—O3	−154.02 (15)
C2—C1—C14—C15	−13.0 (2)	C21—O1—C23—C24	−157.0 (8)
C8—C1—C14—C15	106.85 (19)	C23'—O1—C23—C24	75.1 (19)
C20—C1—C14—C15	−134.48 (18)	C21—O1—C23'—C24'	−103.9 (12)
C2—C1—C14—C19	170.57 (16)	C23—O1—C23'—C24'	−41.9 (15)
C8—C1—C14—C19	−69.6 (2)	C22—O3—C25—C26	−178.7 (2)
C20—C1—C14—C19	49.1 (2)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₆O₄
M_r	402.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.5871 (5), 19.884 (1), 12.7591 (8)
β (°)	97.302 (1)
V (Å³)	2160.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.45 × 0.40

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12570, 4693, 2761
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.151, 1.00
No. of reflections	4693
No. of parameters	290
No. of restraints	28
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

We thank the Key Subject Construction Project of Hunan Province (No. 2006-180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 07A023) and the University of Malaya for supporting this study.

References

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