trans-1,2,3-Tris(4-methoxy­benzo­yl)cyclo­propane

Sun, J.; She, N.

doi:10.1107/S1600536809005145

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o588

doi:10.1107/S1600536809005145

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trans-1,2,3-Tris(4-methoxybenzoyl)cyclopropane

Jingjing Sun ^a ^* and Nengfang She ^a

^aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: ajsun@mails.ccnu.edu.cn

(Received 10 December 2008; accepted 12 February 2009; online 25 February 2009)

In the title compound, C₂₇H₂₄O₆, the packing of the molecules is mainly governed by C—H⋯O interactions.

Related literature

For related structures, see: Saba (1990 ). For background to the chemistry of cyclopropanes as a versatile tool in organic synthesis, see: Wong (1989 ).

Experimental

Crystal data

C₂₇H₂₄O₆
M_r = 444.46
Triclinic, $[P \overline 1]$
a = 10.1897 (6) Å
b = 10.626 (6) Å
c = 10.6931 (6) Å
α = 90.736 (1)°
β = 103.194 (1)°
γ = 92.432 (1)°
V = 1125.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
9852 measured reflections
4349 independent reflections
2862 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.155
S = 1.06
4349 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O2ⁱ	0.93	2.54	3.467 (3)	175
C11—H11⋯O6ⁱⁱ	0.98	2.51	3.270 (3)	134
C7—H7⋯O5ⁱⁱⁱ	0.93	2.52	3.171 (3)	128
C9—H9⋯O3ⁱⁱⁱ	0.98	2.55	3.497 (3)	164
C27—H27B⋯O4^iv	0.96	2.58	3.136 (3)	117
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+2, -z; (iv) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005145/rk2123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005145/rk2123Isup2.hkl

checkCIF report

Comment top

The unusual bonding of cyclopropanes and the strain release associated with cleavage of cyclopropanes offer the possibility of recognizing that structural unit when it is a part of a larger molecule. We report here the molecular structure of the title cyclopropane derivative (Fig. 1), which is an important intermediate in organic synthesis (Saba, 1990). Since numerous methodologies have been developed for the construction of three–membered carbocycles, the chemistry of cyclopropanes has emerged as a versatile tool in organic synthesis (Wong, 1989).

The crystal packing is stabilized by intermolecular C—H···O interaction.

Related literature top

For related structures, see: Saba (1990). For background to the chemistry of cyclopropanes as a versatile tool in organic synthesis, see: Wong (1989).

Experimental top

The title compound was synthesized according to the procedure reported (Saba, 1990). Crystals appropriate for X–ray data collection were obtained by slow evaporation of the dichloromethane solution at 293 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.

trans-1,2,3-Tris(4-methoxybenzoyl)cyclopropane top

Crystal data top

C₂₇H₂₄O₆	Z = 2
M_r = 444.46	F(000) = 468
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1897 (6) Å	Cell parameters from 1774 reflections
b = 10.626 (6) Å	θ = 2.7–21.3°
c = 10.6931 (6) Å	µ = 0.09 mm⁻¹
α = 90.736 (1)°	T = 298 K
β = 103.194 (1)°	Block, colourless
γ = 92.432 (1)°	0.30 × 0.20 × 0.10 mm
V = 1125.9 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2862 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ϕ and ω scans	h = −12→12
9852 measured reflections	k = −10→13
4349 independent reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.057	Hydrogen site location: Geom
wR(F²) = 0.155	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0697P)² + 0.0779P] where P = (F_o² + 2F_c²)/3
4349 reflections	(Δ/σ)_max = 0.001
301 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₇H₂₄O₆	γ = 92.432 (1)°
M_r = 444.46	V = 1125.9 (6) Å³
Triclinic, P1	Z = 2
a = 10.1897 (6) Å	Mo Kα radiation
b = 10.626 (6) Å	µ = 0.09 mm⁻¹
c = 10.6931 (6) Å	T = 298 K
α = 90.736 (1)°	0.30 × 0.20 × 0.10 mm
β = 103.194 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2862 reflections with I > 2σ(I)
9852 measured reflections	R_int = 0.031
4349 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
4349 reflections	Δρ_min = −0.17 e Å⁻³
301 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	1.0074 (3)	1.5583 (3)	0.2073 (3)	0.0938 (10)
H1A	0.9340	1.6141	0.1903	0.141*
H1B	1.0773	1.5892	0.1672	0.141*
H1C	1.0425	1.5543	0.2983	0.141*
C2	0.8628 (2)	1.3733 (2)	0.2028 (2)	0.0559 (6)
C3	0.8010 (3)	1.4209 (2)	0.2944 (2)	0.0632 (7)
H3	0.8256	1.5011	0.3302	0.076*
C4	0.7018 (3)	1.3478 (2)	0.3320 (2)	0.0598 (7)
H4	0.6627	1.3784	0.3961	0.072*
C5	0.6594 (2)	1.2303 (2)	0.27708 (19)	0.0452 (6)
C6	0.7213 (2)	1.1851 (2)	0.1834 (2)	0.0480 (6)
H6	0.6935	1.1070	0.1440	0.058*
C7	0.8233 (2)	1.2554 (2)	0.1489 (2)	0.0578 (7)
H7	0.8662	1.2229	0.0884	0.069*
C8	0.5550 (2)	1.1548 (2)	0.32226 (19)	0.0489 (6)
C9	0.4782 (2)	1.0509 (2)	0.23775 (18)	0.0447 (6)
H9	0.4560	1.0668	0.1454	0.054*
C10	0.3734 (2)	0.9763 (2)	0.28795 (19)	0.0453 (6)
H10	0.3694	0.9979	0.3763	0.054*
C11	0.5019 (2)	0.9174 (2)	0.27438 (19)	0.0452 (6)
H11	0.5681	0.9061	0.3552	0.054*
C12	0.5012 (2)	0.8198 (2)	0.1703 (2)	0.0480 (6)
C13	0.4473 (2)	0.6911 (2)	0.1861 (2)	0.0467 (6)
C14	0.4281 (3)	0.6476 (3)	0.3027 (2)	0.0592 (7)
H14	0.4515	0.6999	0.3756	0.071*
C15	0.3747 (3)	0.5276 (3)	0.3114 (2)	0.0684 (8)
H15	0.3643	0.4989	0.3905	0.082*
C16	0.3365 (3)	0.4493 (2)	0.2036 (2)	0.0571 (6)
C17	0.3553 (3)	0.4921 (3)	0.0870 (2)	0.0578 (7)
H17	0.3294	0.4409	0.0135	0.069*
C18	0.4123 (2)	0.6105 (2)	0.0802 (2)	0.0529 (6)
H18	0.4278	0.6372	0.0021	0.064*
C19	0.2147 (3)	0.2623 (3)	0.1091 (3)	0.0829 (9)
H19A	0.1527	0.3131	0.0523	0.124*
H19B	0.1663	0.1912	0.1343	0.124*
H19C	0.2810	0.2334	0.0659	0.124*
C20	0.2404 (2)	0.9402 (2)	0.20001 (19)	0.0437 (6)
C21	0.1269 (2)	0.9056 (2)	0.25933 (19)	0.0425 (5)
C22	−0.0052 (2)	0.9130 (2)	0.1882 (2)	0.0503 (6)
H22	−0.0211	0.9394	0.1037	0.060*
C23	−0.1126 (2)	0.8816 (2)	0.2419 (2)	0.0582 (7)
H23	−0.2003	0.8875	0.1936	0.070*
C24	−0.0906 (2)	0.8411 (2)	0.3674 (2)	0.0538 (6)
C25	0.0391 (2)	0.8319 (3)	0.4392 (2)	0.0593 (7)
H25	0.0545	0.8039	0.5231	0.071*
C26	0.1462 (2)	0.8650 (2)	0.3847 (2)	0.0534 (6)
H26	0.2337	0.8598	0.4337	0.064*
C27	−0.1880 (3)	0.7676 (3)	0.5382 (3)	0.0860 (9)
H27A	−0.1411	0.6906	0.5457	0.129*
H27B	−0.2753	0.7524	0.5563	0.129*
H27C	−0.1372	0.8295	0.5982	0.129*
O2	0.53287 (17)	1.17456 (18)	0.42848 (14)	0.0672 (5)
O1	0.96041 (19)	1.43598 (18)	0.15687 (19)	0.0816 (6)
O3	0.54286 (18)	0.84862 (17)	0.07605 (15)	0.0635 (5)
O4	0.2801 (2)	0.33557 (18)	0.22053 (17)	0.0786 (6)
O5	0.22625 (15)	0.94253 (16)	0.08352 (13)	0.0579 (5)
O6	−0.20364 (17)	0.8128 (2)	0.41048 (18)	0.0797 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.086 (2)	0.058 (2)	0.140 (3)	−0.0223 (17)	0.036 (2)	−0.0041 (19)
C2	0.0474 (14)	0.0519 (16)	0.0689 (15)	−0.0061 (12)	0.0160 (12)	0.0002 (12)
C3	0.0651 (16)	0.0477 (17)	0.0761 (17)	−0.0103 (13)	0.0178 (13)	−0.0154 (13)
C4	0.0622 (15)	0.0631 (18)	0.0557 (14)	−0.0040 (13)	0.0191 (12)	−0.0128 (12)
C5	0.0447 (12)	0.0474 (15)	0.0409 (11)	−0.0032 (11)	0.0057 (9)	0.0003 (10)
C6	0.0504 (13)	0.0439 (14)	0.0487 (12)	−0.0027 (11)	0.0103 (10)	−0.0032 (10)
C7	0.0532 (14)	0.0607 (18)	0.0636 (15)	−0.0030 (13)	0.0233 (12)	−0.0097 (12)
C8	0.0461 (13)	0.0625 (17)	0.0343 (11)	0.0013 (11)	0.0016 (9)	0.0022 (10)
C9	0.0431 (12)	0.0574 (16)	0.0320 (10)	−0.0077 (11)	0.0073 (9)	0.0032 (10)
C10	0.0432 (12)	0.0569 (15)	0.0354 (10)	−0.0034 (11)	0.0094 (9)	−0.0037 (10)
C11	0.0382 (12)	0.0564 (16)	0.0388 (11)	−0.0011 (10)	0.0047 (9)	0.0037 (10)
C12	0.0381 (12)	0.0635 (17)	0.0435 (12)	0.0040 (11)	0.0115 (10)	0.0020 (11)
C13	0.0441 (12)	0.0542 (16)	0.0445 (12)	0.0069 (11)	0.0149 (10)	0.0039 (10)
C14	0.0696 (17)	0.0643 (19)	0.0442 (13)	−0.0035 (14)	0.0154 (11)	0.0006 (11)
C15	0.091 (2)	0.071 (2)	0.0454 (13)	−0.0064 (16)	0.0213 (13)	0.0065 (13)
C16	0.0659 (16)	0.0509 (17)	0.0565 (14)	0.0060 (13)	0.0171 (12)	0.0070 (12)
C17	0.0695 (17)	0.0575 (18)	0.0483 (13)	0.0088 (13)	0.0168 (12)	−0.0048 (12)
C18	0.0595 (15)	0.0570 (17)	0.0471 (13)	0.0121 (13)	0.0205 (11)	0.0042 (11)
C19	0.099 (2)	0.061 (2)	0.086 (2)	−0.0007 (17)	0.0178 (17)	−0.0101 (15)
C20	0.0434 (12)	0.0473 (15)	0.0403 (12)	0.0001 (10)	0.0101 (9)	−0.0047 (10)
C21	0.0397 (12)	0.0444 (14)	0.0428 (11)	−0.0024 (10)	0.0089 (9)	−0.0008 (10)
C22	0.0469 (13)	0.0543 (16)	0.0471 (12)	−0.0035 (11)	0.0063 (10)	0.0066 (11)
C23	0.0384 (13)	0.0705 (18)	0.0630 (15)	0.0004 (12)	0.0056 (11)	0.0106 (13)
C24	0.0415 (13)	0.0589 (17)	0.0637 (15)	0.0017 (11)	0.0169 (11)	0.0124 (12)
C25	0.0526 (15)	0.0770 (19)	0.0490 (13)	0.0006 (13)	0.0128 (11)	0.0148 (12)
C26	0.0381 (12)	0.0714 (18)	0.0478 (13)	−0.0002 (12)	0.0042 (10)	0.0080 (12)
C27	0.0723 (19)	0.111 (3)	0.086 (2)	0.0035 (18)	0.0399 (16)	0.0242 (18)
O2	0.0693 (11)	0.0922 (14)	0.0383 (9)	−0.0202 (10)	0.0137 (8)	−0.0112 (8)
O1	0.0740 (13)	0.0648 (14)	0.1145 (15)	−0.0186 (10)	0.0440 (11)	−0.0110 (11)
O3	0.0715 (11)	0.0723 (13)	0.0538 (9)	−0.0054 (9)	0.0307 (8)	0.0021 (8)
O4	0.1083 (16)	0.0589 (13)	0.0671 (11)	−0.0104 (11)	0.0191 (10)	0.0065 (9)
O5	0.0540 (10)	0.0799 (13)	0.0384 (8)	−0.0060 (9)	0.0097 (7)	−0.0086 (8)
O6	0.0481 (10)	0.1137 (17)	0.0840 (13)	0.0054 (10)	0.0268 (9)	0.0337 (11)

Geometric parameters (Å, º) top

C1—O1	1.422 (3)	C14—C15	1.378 (3)
C1—H1A	0.9600	C14—H14	0.9300
C1—H1B	0.9600	C15—C16	1.383 (3)
C1—H1C	0.9600	C15—H15	0.9300
C2—O1	1.360 (3)	C16—O4	1.348 (3)
C2—C7	1.377 (3)	C16—C17	1.384 (3)
C2—C3	1.381 (3)	C17—C18	1.373 (3)
C3—C4	1.383 (3)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.381 (3)	C19—O4	1.428 (3)
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.390 (3)	C19—H19B	0.9600
C5—C8	1.477 (3)	C19—H19C	0.9600
C6—C7	1.376 (3)	C20—O5	1.222 (2)
C6—H6	0.9300	C20—C21	1.477 (3)
C7—H7	0.9300	C21—C26	1.387 (3)
C8—O2	1.225 (2)	C21—C22	1.393 (3)
C8—C9	1.492 (3)	C22—C23	1.378 (3)
C9—C11	1.491 (3)	C22—H22	0.9300
C9—C10	1.503 (3)	C23—C24	1.387 (3)
C9—H9	0.9800	C23—H23	0.9300
C10—C20	1.494 (3)	C24—O6	1.358 (3)
C10—C11	1.510 (3)	C24—C25	1.376 (3)
C10—H10	0.9800	C25—C26	1.384 (3)
C11—C12	1.510 (3)	C25—H25	0.9300
C11—H11	0.9800	C26—H26	0.9300
C12—O3	1.218 (2)	C27—O6	1.430 (3)
C12—C13	1.478 (3)	C27—H27A	0.9600
C13—C18	1.382 (3)	C27—H27B	0.9600
C13—C14	1.387 (3)	C27—H27C	0.9600

O1—C1—H1A	109.5	C15—C14—C13	120.5 (2)
O1—C1—H1B	109.5	C15—C14—H14	119.8
H1A—C1—H1B	109.5	C13—C14—H14	119.8
O1—C1—H1C	109.5	C14—C15—C16	120.7 (2)
H1A—C1—H1C	109.5	C14—C15—H15	119.6
H1B—C1—H1C	109.5	C16—C15—H15	119.6
O1—C2—C7	115.4 (2)	O4—C16—C15	116.4 (2)
O1—C2—C3	124.8 (2)	O4—C16—C17	124.5 (2)
C7—C2—C3	119.8 (2)	C15—C16—C17	119.1 (2)
C2—C3—C4	119.1 (2)	C18—C17—C16	119.7 (2)
C2—C3—H3	120.5	C18—C17—H17	120.2
C4—C3—H3	120.5	C16—C17—H17	120.2
C5—C4—C3	121.8 (2)	C17—C18—C13	121.8 (2)
C5—C4—H4	119.1	C17—C18—H18	119.1
C3—C4—H4	119.1	C13—C18—H18	119.1
C4—C5—C6	118.1 (2)	O4—C19—H19A	109.5
C4—C5—C8	119.8 (2)	O4—C19—H19B	109.5
C6—C5—C8	122.0 (2)	H19A—C19—H19B	109.5
C7—C6—C5	120.3 (2)	O4—C19—H19C	109.5
C7—C6—H6	119.8	H19A—C19—H19C	109.5
C5—C6—H6	119.8	H19B—C19—H19C	109.5
C6—C7—C2	120.8 (2)	O5—C20—C21	121.68 (18)
C6—C7—H7	119.6	O5—C20—C10	120.80 (19)
C2—C7—H7	119.6	C21—C20—C10	117.50 (17)
O2—C8—C5	121.07 (19)	C26—C21—C22	117.9 (2)
O2—C8—C9	119.9 (2)	C26—C21—C20	122.47 (19)
C5—C8—C9	119.03 (18)	C22—C21—C20	119.67 (19)
C11—C9—C8	119.55 (18)	C23—C22—C21	120.6 (2)
C11—C9—C10	60.57 (15)	C23—C22—H22	119.7
C8—C9—C10	117.15 (17)	C21—C22—H22	119.7
C11—C9—H9	116.0	C22—C23—C24	120.4 (2)
C8—C9—H9	116.0	C22—C23—H23	119.8
C10—C9—H9	116.0	C24—C23—H23	119.8
C20—C10—C9	119.72 (17)	O6—C24—C25	124.6 (2)
C20—C10—C11	121.69 (18)	O6—C24—C23	115.4 (2)
C9—C10—C11	59.33 (14)	C25—C24—C23	120.0 (2)
C20—C10—H10	114.9	C24—C25—C26	119.1 (2)
C9—C10—H10	114.9	C24—C25—H25	120.5
C11—C10—H10	114.9	C26—C25—H25	120.5
C9—C11—C10	60.10 (15)	C25—C26—C21	122.0 (2)
C9—C11—C12	118.96 (18)	C25—C26—H26	119.0
C10—C11—C12	121.17 (17)	C21—C26—H26	119.0
C9—C11—H11	115.2	O6—C27—H27A	109.5
C10—C11—H11	115.2	O6—C27—H27B	109.5
C12—C11—H11	115.2	H27A—C27—H27B	109.5
O3—C12—C13	121.9 (2)	O6—C27—H27C	109.5
O3—C12—C11	119.9 (2)	H27A—C27—H27C	109.5
C13—C12—C11	118.13 (19)	H27B—C27—H27C	109.5
C18—C13—C14	118.1 (2)	C2—O1—C1	119.2 (2)
C18—C13—C12	119.0 (2)	C16—O4—C19	118.2 (2)
C14—C13—C12	122.9 (2)	C24—O6—C27	118.2 (2)

O1—C2—C3—C4	179.4 (2)	C18—C13—C14—C15	−0.5 (4)
C7—C2—C3—C4	1.2 (4)	C12—C13—C14—C15	178.6 (2)
C2—C3—C4—C5	−2.5 (4)	C13—C14—C15—C16	−1.4 (4)
C3—C4—C5—C6	1.4 (4)	C14—C15—C16—O4	−177.3 (2)
C3—C4—C5—C8	178.9 (2)	C14—C15—C16—C17	1.4 (4)
C4—C5—C6—C7	1.1 (3)	O4—C16—C17—C18	179.2 (2)
C8—C5—C6—C7	−176.4 (2)	C15—C16—C17—C18	0.6 (4)
C5—C6—C7—C2	−2.3 (4)	C16—C17—C18—C13	−2.5 (4)
O1—C2—C7—C6	−177.2 (2)	C14—C13—C18—C17	2.5 (4)
C3—C2—C7—C6	1.1 (4)	C12—C13—C18—C17	−176.6 (2)
C4—C5—C8—O2	−21.4 (3)	C9—C10—C20—O5	18.0 (3)
C6—C5—C8—O2	156.0 (2)	C11—C10—C20—O5	−52.3 (3)
C4—C5—C8—C9	160.2 (2)	C9—C10—C20—C21	−160.3 (2)
C6—C5—C8—C9	−22.4 (3)	C11—C10—C20—C21	129.4 (2)
O2—C8—C9—C11	−68.5 (3)	O5—C20—C21—C26	159.8 (2)
C5—C8—C9—C11	109.9 (2)	C10—C20—C21—C26	−21.9 (3)
O2—C8—C9—C10	1.3 (3)	O5—C20—C21—C22	−20.1 (3)
C5—C8—C9—C10	179.8 (2)	C10—C20—C21—C22	158.2 (2)
C11—C9—C10—C20	−111.4 (2)	C26—C21—C22—C23	0.4 (3)
C8—C9—C10—C20	138.3 (2)	C20—C21—C22—C23	−179.7 (2)
C8—C9—C10—C11	−110.3 (2)	C21—C22—C23—C24	−0.5 (4)
C8—C9—C11—C10	106.4 (2)	C22—C23—C24—O6	179.9 (2)
C8—C9—C11—C12	−142.2 (2)	C22—C23—C24—C25	−0.1 (4)
C10—C9—C11—C12	111.4 (2)	O6—C24—C25—C26	−179.3 (2)
C20—C10—C11—C9	108.1 (2)	C23—C24—C25—C26	0.7 (4)
C20—C10—C11—C12	0.4 (3)	C24—C25—C26—C21	−0.8 (4)
C9—C10—C11—C12	−107.8 (2)	C22—C21—C26—C25	0.3 (4)
C9—C11—C12—O3	33.7 (3)	C20—C21—C26—C25	−179.6 (2)
C10—C11—C12—O3	104.4 (3)	C7—C2—O1—C1	−179.9 (3)
C9—C11—C12—C13	−145.5 (2)	C3—C2—O1—C1	1.9 (4)
C10—C11—C12—C13	−74.8 (3)	C15—C16—O4—C19	167.5 (2)
O3—C12—C13—C18	−16.1 (3)	C17—C16—O4—C19	−11.1 (4)
C11—C12—C13—C18	163.0 (2)	C25—C24—O6—C27	−1.4 (4)
O3—C12—C13—C14	164.8 (2)	C23—C24—O6—C27	178.6 (3)
C11—C12—C13—C14	−16.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O2ⁱ	0.93	2.54	3.467 (3)	175
C11—H11···O6ⁱⁱ	0.98	2.51	3.270 (3)	134
C7—H7···O5ⁱⁱⁱ	0.93	2.52	3.171 (3)	128
C9—H9···O3ⁱⁱⁱ	0.98	2.55	3.497 (3)	164
C27—H27B···O4^iv	0.96	2.58	3.136 (3)	117

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄O₆
M_r	444.46
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.1897 (6), 10.626 (6), 10.6931 (6)
α, β, γ (°)	90.736 (1), 103.194 (1), 92.432 (1)
V (Å³)	1125.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9852, 4349, 2862
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.155, 1.06
No. of reflections	4349
No. of parameters	301
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O2ⁱ	0.93	2.54	3.467 (3)	174.9
C11—H11···O6ⁱⁱ	0.98	2.51	3.270 (3)	133.7
C7—H7···O5ⁱⁱⁱ	0.93	2.52	3.171 (3)	127.5
C9—H9···O3ⁱⁱⁱ	0.98	2.55	3.497 (3)	163.6
C27—H27B···O4^iv	0.96	2.58	3.136 (3)	116.7

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x, −y+1, −z+1.

Acknowledgements

The authors thank Professor An–Xin Wu for technical assistance and Dr Xiang–Gao Meng for the data collection.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Saba, A. (1990). J. Chem. Res. Synop. 9, 288–289. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wong, H. N. C. (1989). Chem. Rev. 89, 165–198. CrossRef CAS Web of Science Google Scholar