(E)-3-(2,4-Dimeth­oxy­phen­yl)-1-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Wu, J.; Qiu, J.; Wu, X.; Yang, S.; Liu, Y.

doi:10.1107/S1600536811053001

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o154

doi:10.1107/S1600536811053001

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(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Jianzhang Wu,^a,^b Junyan Qiu,^c Xiaokai Wu,^c Shulin Yang ^a and Yonggen Liu ^d ^*

^aInstitute of Biotechnology, Nanjing University of Science and Technology, Nanjing, Jiangsu Province 210094, People's Republic of China, ^bSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, ^cLife Science College, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and ^dSchool of Pharmacy, Hainan Medical College, Haikou, Hainan Province 571101, People's Republic of China
^*Correspondence e-mail: wjzwzmc@126.com

(Received 4 December 2011; accepted 9 December 2011; online 17 December 2011)

In the title chalcone derivative, C₂₀H₂₂O₆, the dihedral angle between the mean planes of the benzene rings is 15.77 (6)°. The H atoms of the central C=C double bond are in a trans configuration. There are a number of C—H⋯O interactions and a C—H⋯π interaction present in the crystal structure.

Related literature

For related structures, see: Wu et al. (2010 , 2011 ); Huang et al. (2010 ); Peng et al. (2010 ). For applications of chalcones, see: Wu et al. (2010, 2011); Nielsen et al. (2005 ). For the hydrogen-bond analysis, see: Spek (2009 ).

Experimental

Crystal data

C₂₀H₂₂O₆
M_r = 358.38
Monoclinic, P 2₁ /c
a = 8.3111 (11) Å
b = 13.8493 (17) Å
c = 15.887 (2) Å
β = 101.588 (2)°
V = 1791.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.40 × 0.37 × 0.31 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.651, T_max = 1.000
9663 measured reflections
3512 independent reflections
2452 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.126
S = 0.97
3512 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O6ⁱ	0.93	2.65	3.562 (2)	166
C18—H18B⋯O3ⁱⁱ	0.96	2.64	3.404 (2)	136
C16—H16B⋯O2ⁱⁱⁱ	0.96	2.68	3.389 (2)	132
C16—H16C⋯O1ⁱⁱⁱ	0.96	2.66	3.608 (3)	169
C19—H19C⋯Cg1^iv	0.96	2.79	3.530 (2)	134
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z.

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 I, global. DOI: 10.1107/S1600536811053001/zq2146sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053001/zq2146Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053001/zq2146Isup3.cml

checkCIF report

Comment top

Chalcones are characterized by possessing two aromatic rings linked by a three-carbon α,β-unsaturated carbonyl system (Wu et al., 2010; Wu et al., 2011). Natural chalcones have many kinds of active biological properties such as antiinflammatory, antitumoral, antimalarial, antileishmanial, Antibacterial. Investigations have demonstrated that synthetical chalcones have the same biological properties as natural chalcones. (Wu et al. 2010; Wu et al. 2011; Nielsen et al. 2005). In order to study its anticancer agents, we have synthesized the title chalcone derivative and herein its crystal structure is reported. The crystal structure parameters are similar to those found in some analogous structures reported in the literature (Peng et al., 2010; Huang et al., 2010).The dihedral angle between the mean planes of the phenyl rings is 15.77 (6)°. The H atoms of the central C=C double bond are in a trans configuration. In the crystal structure, there are many weak C–H···O intermolecular contacts (Table 1) but no classic hydrogen bonds between the molecules (Spek, 2009).

Related literature top

For related structures, see: Wu et al. (2010, 2011); Huang et al. (2010); Peng et al. (2010). For applications of chalcones, see: Wu et al. (2010, 2011); Nielsen et al. (2005). For the hydrogen-bond analysis, see: Spek (2009).

Experimental top

The title compound was synthesized by Claisen-Schmidt condensation between 2,4-dimethoxybenzaldehyde and 1-(3,4,5-trimethoxyphenyl)ethanone. 2,4-Dimethoxybenzaldehyde (1 mmol) and 1-(3,4,5-trimethoxyphenyl)ethanone (1 mmol) were dissolved in ehanol (20 ml). The reaction temperature was controlled at 283 K, and then NaOH (20%, 3 drops) was added. The reaction was monitored by thin-layer chromatography. 20 ml H₂O was added 5 h later and the yellow solid precipitated. It was washed with a mixture of water and cold ethanol, and dried (yield: 70%; mp 125.7–127.7°C). Single crystals of the title compound were obtained by recrystallization from a solution of CH₃CH₂OH / CH₂Cl₂ at 293 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Sheldrick, 2008); 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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound viewed down the a axis.

(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₀H₂₂O₆	F(000) = 760
M_r = 358.38	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2728 reflections
a = 8.3111 (11) Å	θ = 5.2–49.2°
b = 13.8493 (17) Å	µ = 0.10 mm⁻¹
c = 15.887 (2) Å	T = 293 K
β = 101.588 (2)°	Prismatic, green
V = 1791.4 (4) Å³	0.40 × 0.37 × 0.31 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3512 independent reflections
Radiation source: fine-focus sealed tube	2452 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
phi and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→9
T_min = 0.651, T_max = 1.000	k = −17→15
9663 measured reflections	l = −16→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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0689P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3512 reflections	Δρ_max = 0.20 e Å⁻³
241 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (15)

Crystal data top

C₂₀H₂₂O₆	V = 1791.4 (4) Å³
M_r = 358.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3111 (11) Å	µ = 0.10 mm⁻¹
b = 13.8493 (17) Å	T = 293 K
c = 15.887 (2) Å	0.40 × 0.37 × 0.31 mm
β = 101.588 (2)°

Data collection top

Bruker SMART CCD diffractometer	3512 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2452 reflections with I > 2σ(I)
T_min = 0.651, T_max = 1.000	R_int = 0.045
9663 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 0.97	Δρ_max = 0.20 e Å⁻³
3512 reflections	Δρ_min = −0.19 e Å⁻³
241 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	0.3078 (3)	0.60842 (10)	−0.03257 (9)	0.0969 (7)
O2	0.45908 (16)	0.73756 (8)	0.24726 (7)	0.0510 (4)
O3	0.34229 (18)	0.58134 (9)	0.49898 (7)	0.0629 (4)
O4	0.20538 (17)	0.38935 (8)	−0.28996 (7)	0.0549 (4)
O5	0.11723 (15)	0.21987 (8)	−0.23292 (7)	0.0487 (3)
O6	0.07241 (18)	0.19802 (8)	−0.07336 (8)	0.0614 (4)
C1	0.2622 (3)	0.53394 (12)	−0.00427 (11)	0.0532 (5)
C2	0.2513 (2)	0.52558 (12)	0.08616 (11)	0.0494 (5)
H2	0.1994	0.4719	0.1037	0.059*
C3	0.3124 (2)	0.59147 (12)	0.14391 (11)	0.0478 (5)
H3	0.3597	0.6450	0.1231	0.057*
C4	0.3155 (2)	0.59116 (11)	0.23532 (10)	0.0397 (4)
C5	0.3969 (2)	0.66447 (11)	0.28813 (10)	0.0395 (4)
C6	0.4097 (2)	0.66259 (11)	0.37629 (10)	0.0438 (4)
H6	0.4670	0.7109	0.4104	0.053*
C7	0.3368 (2)	0.58853 (12)	0.41331 (11)	0.0454 (4)
C8	0.2505 (2)	0.51675 (12)	0.36245 (12)	0.0495 (5)
H8	0.1993	0.4677	0.3872	0.059*
C9	0.2416 (2)	0.51894 (11)	0.27580 (11)	0.0456 (5)
H9	0.1839	0.4703	0.2423	0.055*
C10	0.2178 (2)	0.44929 (11)	−0.06312 (10)	0.0441 (5)
C11	0.2324 (2)	0.46042 (11)	−0.14787 (11)	0.0451 (4)
H11	0.2675	0.5192	−0.1662	0.054*
C12	0.1956 (2)	0.38529 (11)	−0.20524 (10)	0.0428 (4)
C13	0.1453 (2)	0.29723 (11)	−0.17775 (10)	0.0407 (4)
C14	0.1279 (2)	0.28626 (11)	−0.09326 (11)	0.0436 (4)
C15	0.1647 (2)	0.36210 (11)	−0.03595 (11)	0.0468 (5)
H15	0.1538	0.3545	0.0208	0.056*
C16	0.4271 (3)	0.65505 (15)	0.55295 (12)	0.0817 (8)
H16A	0.5415	0.6534	0.5505	0.123*
H16B	0.4147	0.6445	0.6110	0.123*
H16C	0.3821	0.7169	0.5336	0.123*
C17	0.5458 (2)	0.81254 (12)	0.29860 (11)	0.0517 (5)
H17A	0.4751	0.8421	0.3321	0.078*
H17B	0.5805	0.8601	0.2621	0.078*
H17C	0.6402	0.7859	0.3363	0.078*
C18	0.2455 (3)	0.47971 (13)	−0.32250 (12)	0.0632 (6)
H18A	0.1629	0.5263	−0.3168	0.095*
H18B	0.2508	0.4730	−0.3820	0.095*
H18C	0.3501	0.5010	−0.2907	0.095*
C19	−0.0442 (2)	0.21605 (14)	−0.28238 (13)	0.0635 (6)
H19A	−0.1204	0.2052	−0.2452	0.095*
H19B	−0.0523	0.1643	−0.3232	0.095*
H19C	−0.0697	0.2761	−0.3123	0.095*
C20	0.0313 (3)	0.18677 (15)	0.00746 (13)	0.0796 (7)
H20A	0.1280	0.1943	0.0515	0.119*
H20B	−0.0141	0.1236	0.0115	0.119*
H20C	−0.0483	0.2347	0.0147	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.196 (2)	0.0472 (8)	0.0459 (9)	−0.0398 (10)	0.0199 (10)	−0.0057 (6)
O2	0.0720 (9)	0.0430 (7)	0.0373 (7)	−0.0161 (6)	0.0091 (6)	−0.0008 (5)
O3	0.1002 (12)	0.0532 (8)	0.0383 (7)	−0.0019 (7)	0.0214 (7)	0.0041 (6)
O4	0.0851 (10)	0.0457 (7)	0.0366 (7)	−0.0065 (6)	0.0188 (6)	−0.0026 (5)
O5	0.0564 (8)	0.0391 (6)	0.0498 (7)	0.0031 (6)	0.0088 (6)	−0.0121 (5)
O6	0.0974 (11)	0.0389 (7)	0.0520 (8)	−0.0099 (7)	0.0252 (7)	−0.0010 (6)
C1	0.0786 (14)	0.0389 (10)	0.0384 (10)	−0.0011 (9)	0.0028 (9)	−0.0016 (8)
C2	0.0649 (13)	0.0396 (9)	0.0429 (10)	−0.0037 (9)	0.0092 (9)	−0.0034 (8)
C3	0.0658 (13)	0.0363 (9)	0.0400 (10)	−0.0048 (8)	0.0076 (8)	−0.0006 (7)
C4	0.0486 (11)	0.0334 (8)	0.0364 (9)	0.0030 (7)	0.0067 (8)	−0.0017 (7)
C5	0.0473 (10)	0.0338 (8)	0.0375 (9)	−0.0002 (7)	0.0087 (8)	0.0010 (7)
C6	0.0574 (12)	0.0376 (9)	0.0353 (9)	−0.0013 (8)	0.0065 (8)	−0.0034 (7)
C7	0.0625 (12)	0.0395 (9)	0.0361 (10)	0.0095 (8)	0.0141 (8)	0.0039 (7)
C8	0.0659 (13)	0.0354 (9)	0.0514 (11)	−0.0025 (8)	0.0217 (9)	0.0041 (8)
C9	0.0551 (12)	0.0338 (9)	0.0484 (11)	−0.0019 (8)	0.0119 (9)	−0.0064 (7)
C10	0.0560 (12)	0.0377 (9)	0.0353 (9)	0.0018 (8)	0.0018 (8)	−0.0013 (7)
C11	0.0581 (12)	0.0353 (9)	0.0410 (10)	−0.0034 (8)	0.0078 (8)	0.0011 (7)
C12	0.0520 (11)	0.0412 (9)	0.0354 (9)	0.0038 (8)	0.0094 (8)	−0.0016 (7)
C13	0.0466 (11)	0.0343 (9)	0.0402 (10)	0.0047 (7)	0.0066 (8)	−0.0052 (7)
C14	0.0537 (11)	0.0328 (9)	0.0440 (10)	0.0007 (8)	0.0086 (8)	0.0008 (7)
C15	0.0641 (13)	0.0422 (10)	0.0334 (9)	0.0020 (9)	0.0082 (8)	0.0010 (7)
C16	0.138 (2)	0.0694 (14)	0.0348 (11)	−0.0064 (14)	0.0103 (12)	−0.0023 (10)
C17	0.0619 (13)	0.0421 (10)	0.0515 (11)	−0.0131 (9)	0.0125 (9)	−0.0037 (8)
C18	0.0934 (17)	0.0537 (12)	0.0456 (11)	−0.0055 (11)	0.0211 (11)	0.0058 (9)
C19	0.0649 (14)	0.0589 (12)	0.0627 (13)	−0.0058 (10)	0.0032 (10)	−0.0159 (10)
C20	0.117 (2)	0.0644 (14)	0.0642 (14)	−0.0289 (14)	0.0338 (13)	0.0030 (11)

Geometric parameters (Å, º) top

O1—C1	1.216 (2)	C9—H9	0.9300
O2—C5	1.3595 (19)	C10—C15	1.384 (2)
O2—C17	1.4235 (18)	C10—C11	1.385 (2)
O3—C7	1.3564 (19)	C11—C12	1.377 (2)
O3—C16	1.425 (2)	C11—H11	0.9300
O4—C12	1.366 (2)	C12—C13	1.388 (2)
O4—C18	1.419 (2)	C13—C14	1.387 (2)
O5—C13	1.3742 (18)	C14—C15	1.383 (2)
O5—C19	1.413 (2)	C15—H15	0.9300
O6—C14	1.3656 (19)	C16—H16A	0.9600
O6—C20	1.402 (2)	C16—H16B	0.9600
C1—C2	1.462 (2)	C16—H16C	0.9600
C1—C10	1.499 (2)	C17—H17A	0.9600
C2—C3	1.321 (2)	C17—H17B	0.9600
C2—H2	0.9300	C17—H17C	0.9600
C3—C4	1.447 (2)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C9	1.396 (2)	C18—H18C	0.9600
C4—C5	1.402 (2)	C19—H19A	0.9600
C5—C6	1.383 (2)	C19—H19B	0.9600
C6—C7	1.381 (2)	C19—H19C	0.9600
C6—H6	0.9300	C20—H20A	0.9600
C7—C8	1.387 (2)	C20—H20B	0.9600
C8—C9	1.364 (2)	C20—H20C	0.9600
C8—H8	0.9300

C5—O2—C17	117.82 (13)	C11—C12—C13	119.79 (16)
C7—O3—C16	117.64 (15)	O5—C13—C14	119.64 (14)
C12—O4—C18	117.40 (13)	O5—C13—C12	120.52 (15)
C13—O5—C19	113.86 (13)	C14—C13—C12	119.82 (14)
C14—O6—C20	117.86 (14)	O6—C14—C15	124.57 (16)
O1—C1—C2	121.06 (15)	O6—C14—C13	115.33 (14)
O1—C1—C10	119.26 (16)	C15—C14—C13	120.10 (15)
C2—C1—C10	119.67 (15)	C14—C15—C10	119.96 (16)
C3—C2—C1	122.45 (17)	C14—C15—H15	120.0
C3—C2—H2	118.8	C10—C15—H15	120.0
C1—C2—H2	118.8	O3—C16—H16A	109.5
C2—C3—C4	128.42 (17)	O3—C16—H16B	109.5
C2—C3—H3	115.8	H16A—C16—H16B	109.5
C4—C3—H3	115.8	O3—C16—H16C	109.5
C9—C4—C5	116.56 (15)	H16A—C16—H16C	109.5
C9—C4—C3	122.93 (14)	H16B—C16—H16C	109.5
C5—C4—C3	120.50 (15)	O2—C17—H17A	109.5
O2—C5—C6	122.56 (14)	O2—C17—H17B	109.5
O2—C5—C4	115.95 (14)	H17A—C17—H17B	109.5
C6—C5—C4	121.48 (15)	O2—C17—H17C	109.5
C7—C6—C5	119.61 (15)	H17A—C17—H17C	109.5
C7—C6—H6	120.2	H17B—C17—H17C	109.5
C5—C6—H6	120.2	O4—C18—H18A	109.5
O3—C7—C6	123.55 (15)	O4—C18—H18B	109.5
O3—C7—C8	116.18 (16)	H18A—C18—H18B	109.5
C6—C7—C8	120.26 (16)	O4—C18—H18C	109.5
C9—C8—C7	119.28 (16)	H18A—C18—H18C	109.5
C9—C8—H8	120.4	H18B—C18—H18C	109.5
C7—C8—H8	120.4	O5—C19—H19A	109.5
C8—C9—C4	122.75 (16)	O5—C19—H19B	109.5
C8—C9—H9	118.6	H19A—C19—H19B	109.5
C4—C9—H9	118.6	O5—C19—H19C	109.5
C15—C10—C11	119.75 (15)	H19A—C19—H19C	109.5
C15—C10—C1	122.81 (15)	H19B—C19—H19C	109.5
C11—C10—C1	117.44 (15)	O6—C20—H20A	109.5
C12—C11—C10	120.55 (16)	O6—C20—H20B	109.5
C12—C11—H11	119.7	H20A—C20—H20B	109.5
C10—C11—H11	119.7	O6—C20—H20C	109.5
O4—C12—C11	124.89 (16)	H20A—C20—H20C	109.5
O4—C12—C13	115.31 (14)	H20B—C20—H20C	109.5

O1—C1—C2—C3	−10.4 (3)	O1—C1—C10—C11	0.4 (3)
C10—C1—C2—C3	169.13 (18)	C2—C1—C10—C11	−179.08 (17)
C1—C2—C3—C4	−177.75 (18)	C15—C10—C11—C12	−0.4 (3)
C2—C3—C4—C9	−3.8 (3)	C1—C10—C11—C12	179.24 (17)
C2—C3—C4—C5	175.28 (19)	C18—O4—C12—C11	−4.6 (3)
C17—O2—C5—C6	2.4 (2)	C18—O4—C12—C13	175.86 (16)
C17—O2—C5—C4	−178.70 (15)	C10—C11—C12—O4	179.65 (16)
C9—C4—C5—O2	−175.91 (14)	C10—C11—C12—C13	−0.8 (3)
C3—C4—C5—O2	5.0 (2)	C19—O5—C13—C14	94.45 (19)
C9—C4—C5—C6	3.0 (2)	C19—O5—C13—C12	−87.4 (2)
C3—C4—C5—C6	−176.14 (16)	O4—C12—C13—O5	3.3 (2)
O2—C5—C6—C7	176.89 (15)	C11—C12—C13—O5	−176.24 (15)
C4—C5—C6—C7	−1.9 (3)	O4—C12—C13—C14	−178.56 (15)
C16—O3—C7—C6	0.5 (3)	C11—C12—C13—C14	1.9 (3)
C16—O3—C7—C8	−178.72 (18)	C20—O6—C14—C15	7.9 (3)
C5—C6—C7—O3	−179.56 (16)	C20—O6—C14—C13	−171.57 (17)
C5—C6—C7—C8	−0.4 (3)	O5—C13—C14—O6	−4.1 (2)
O3—C7—C8—C9	−179.29 (16)	C12—C13—C14—O6	177.80 (15)
C6—C7—C8—C9	1.5 (3)	O5—C13—C14—C15	176.41 (15)
C7—C8—C9—C4	−0.3 (3)	C12—C13—C14—C15	−1.7 (3)
C5—C4—C9—C8	−1.9 (3)	O6—C14—C15—C10	−178.97 (16)
C3—C4—C9—C8	177.22 (17)	C13—C14—C15—C10	0.5 (3)
O1—C1—C10—C15	−180.0 (2)	C11—C10—C15—C14	0.6 (3)
C2—C1—C10—C15	0.6 (3)	C1—C10—C15—C14	−179.05 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O6ⁱ	0.93	2.65	3.562 (2)	166
C18—H18B···O3ⁱⁱ	0.96	2.64	3.404 (2)	136
C16—H16B···O2ⁱⁱⁱ	0.96	2.68	3.389 (2)	132
C16—H16C···O1ⁱⁱⁱ	0.96	2.66	3.608 (3)	169
C19—H19C···Cg1^iv	0.96	2.79	3.530 (2)	134

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y, z−1; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂O₆
M_r	358.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.3111 (11), 13.8493 (17), 15.887 (2)
β (°)	101.588 (2)
V (Å³)	1791.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.37 × 0.31

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.651, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9663, 3512, 2452
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.126, 0.97
No. of reflections	3512
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O6ⁱ	0.93	2.65	3.562 (2)	166
C18—H18B···O3ⁱⁱ	0.96	2.64	3.404 (2)	136
C16—H16B···O2ⁱⁱⁱ	0.96	2.68	3.389 (2)	132
C16—H16C···O1ⁱⁱⁱ	0.96	2.66	3.608 (3)	169
C19—H19C···Cg1^iv	0.96	2.79	3.530 (2)	134

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, y, z−1; (iii) x, −y+3/2, z+1/2; (iv) −x, −y+1, −z.

Acknowledgements

The authors are grateful to the associate researcher Sun Jie from Shanghai Institute of Organic Chemistry, Chinese academy of Sciences for testing and crystal analysis. This study was partially supported by the Zhejiang Natural Science Funds (Y2101108) and the University Students in Zhejiang Science and Technology Innovation Projects (2011R413025).

References

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Volume 68| Part 1| January 2012| Page o154

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