2,4-Dimeth­oxy-6-[(E)-2-(4-meth­oxy­phenyl)ethen­yl]benzaldehyde

Ge, X.-L.; Guan, Q.-X.; Deng, S.-S.; Ruan, B.-F.

doi:10.1107/S1600536813007964

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o629

https://doi.org/10.1107/S1600536813007964

Open

access

2,4-Dimethoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]benzaldehyde

Xiao-Lin Ge,^a Qiu-Xiang Guan,^a Sheng-Song Deng ^a and Ban-Feng Ruan ^a ^*

^aSchool of Medical Engineering, Hefei University of Technology, Hefei 230009, People's Republic of China
^*Correspondence e-mail: ruanbf@hfut.edu.cn

(Received 14 March 2013; accepted 22 March 2013; online 5 April 2013)

There are two conformationally similar molecules in the asymmetric unit of he title compound, C₁₈H₁₈O₄, in which the dihedral angles between the benzene rings are 23.54 (12) and 31.11 (12)°. In the crystal, C—H⋯π interactions (minimum H⋯ring centroid distance = 2.66 Å) link the molecules into a layered structure extending down a.

Related literature

The title compound is a derivative of the natural product resveratrol (trans-3,4,5-trihydroxystilbene). For background to resveratrol, see: Jang et al. (1997 ); Orsini et al. (1997 ); Pettit et al. (2002 ). For standard bond lengths and angles, see: Boumendjel et al. (2008 ). For the synthesis of the title compound, see: Huang et al. (2007 ).

Experimental

Crystal data

C₁₈H₁₈O₄
M_r = 298.32
Triclinic, $[P \overline 1]$
a = 9.292 (5) Å
b = 9.448 (5) Å
c = 17.547 (5) Å
α = 84.097 (5)°
β = 84.040 (5)°
γ = 83.315 (5)°
V = 1515.3 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.973, T_max = 0.982
10535 measured reflections
5272 independent reflections
3060 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.168
S = 0.79
5272 reflections
404 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C12–C17 and C30–C35 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cg4ⁱ	0.93	2.88	3.597 (3)	135
C17—H14⋯Cg4ⁱⁱ	0.93	2.76	3.471 (3)	134
C32—H14⋯Cg2	0.93	2.82	3.530 (3)	135
C15—H14⋯Cg2ⁱⁱⁱ	0.93	2.66	3.371 (3)	134
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: https://doi.org/10.1107/S1600536813007964/zs2252sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813007964/zs2252Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813007964/zs2252Isup3.ps

Supporting information file. DOI: https://doi.org/10.1107/S1600536813007964/zs2252Isup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536813007964/zs2252Isup5.cml

checkCIF report

Comment top

Resveratrol (trans-3,4,,5-trihydroxystilbene), a naturally occurring phytoalexin present in medicinal plants, grape skin, peanuts and red wine, has attracted a great deal of attention because it has been suggested as a possible cancer chemopreventive agent on the basis of its inhibitory effects on tumor initiation, promotion, and progression (Jang et al., 1997; Orsini et al., 1997; Pettit et al., 2002). In order to discover novel antitumor agents with high efficiency, a broad spectrum and safety, several series of derivatives of resveratrol were prepared in our laboratory. As an important intermediate, the title compound 2,4-dimethoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]benzaldehyde, was synthesized by the reaction of resveratrol using the Vilslmeier reaction and herein we report the crystal structure.

The title compound, C18 H18 O4, crystallizes in the triclinic space group P-1 with two independent molecules in the asymmetric unit (Fig. 1). All bond lengths are within normal ranges (Boumendjel et al., 2008). The C10—C11 and C28—C29 bond lengths [1.319 (3) and 1.323 (3) Å] are consistent with the expected value for a C—C double bond and similarly, the C7—O1 and C25—O5 bond lengths [1.196 (3) and 1.210 (3) Å] are consistent with the expected value for a carbonyl C—O double bond. The dihedral angle between the two phenyl rings in each are 23.54 (12)° [C1–C6 (ring 1) and C12–C17) (ring 2)] and 31.11 (12)° [C19–C24 (ring 3) and C30–C35 (ring 4)]. As such, the structural differences between the two molecules in the title compound are only marginal.

In the crystal, the two molecules associate through C—H···pi stacking interactions [C14—H14···Cg(4)ⁱ; C17—H···Cg(4)ⁱⁱ; C32—H···Cg(2)ⁱⁱⁱ; C35—H···Cg(2)^iv: H···Cg = 2.88, 2.76, 2.82, 2.66 Å respectively] [for symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 1, -y, -z + 1; (iii) x, y, z; (iv) x + 1, y, z]. Intermolecular methoxy C26—H···O8^v interactions [3.041 (4) Å] across an inversion centre generate a sheet structure (Fig. 2) [for symmetry code (v): -x + 2, -y, -z + 1]. Present also in the structure are intramolecular C—H···O interactions between the aldehyde and ethylenic donors and methoxy O-atom acceptors (Table 1).

Related literature top

The title compound is a derivative of the natural product resveratrol (trans-3,4,5-trihydroxystilbene). For background to resveratrol, see: Jang et al. (1997); Orsini et al. (1997); Pettit et al. (2002). For standard bond lengths and angles, see: Boumendjel et al. (2008). For the synthesis of the title compound, see: Huang et al. (2007).

Experimental top

Title compound was synthesized according to the reported method (Huang et al., 2007). Crystals suitable for X-ray structure analysis were obtained by slow evaporation of a solution of the title compound in a petroleum ether/ dichloromethane mixture (1:1, v/v) at room temperature.

Structure description top

The title compound is a derivative of the natural product resveratrol (trans-3,4,5-trihydroxystilbene). For background to resveratrol, see: Jang et al. (1997); Orsini et al. (1997); Pettit et al. (2002). For standard bond lengths and angles, see: Boumendjel et al. (2008). For the synthesis of the title compound, see: Huang et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 and atom numbering scheme for the two independent molecules of the title compound in the asymmetric unit, showing 30% probability displacement ellipsoids.
	Fig. 2. The layered structure of title compound formed through C—H···pi stacking interactions. Non-interactive H-atoms are omitted.

2,4-Dimethoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]benzaldehyde top

Crystal data top

C₁₈H₁₈O₄	Z = 4
M_r = 298.32	F(000) = 632
Triclinic, P1	D_x = 1.308 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.292 (5) Å	Cell parameters from 1909 reflections
b = 9.448 (5) Å	θ = 2.2–26.7°
c = 17.547 (5) Å	µ = 0.09 mm⁻¹
α = 84.097 (5)°	T = 298 K
β = 84.040 (5)°	Block, colourless
γ = 83.315 (5)°	0.30 × 0.20 × 0.20 mm
V = 1515.3 (12) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5272 independent reflections
Radiation source: fine-focus sealed tube	3060 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
T_min = 0.973, T_max = 0.982	k = −11→11
10535 measured reflections	l = −20→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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.1P)² + 0.699P] where P = (F_o² + 2F_c²)/3
S = 0.79	(Δ/σ)_max < 0.001
5272 reflections	Δρ_max = 0.15 e Å⁻³
404 parameters	Δρ_min = −0.18 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: 0.017 (2)

Crystal data top

C₁₈H₁₈O₄	γ = 83.315 (5)°
M_r = 298.32	V = 1515.3 (12) Å³
Triclinic, P1	Z = 4
a = 9.292 (5) Å	Mo Kα radiation
b = 9.448 (5) Å	µ = 0.09 mm⁻¹
c = 17.547 (5) Å	T = 298 K
α = 84.097 (5)°	0.30 × 0.20 × 0.20 mm
β = 84.040 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5272 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3060 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.039
10535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 0.79	Δρ_max = 0.15 e Å⁻³
5272 reflections	Δρ_min = −0.18 e Å⁻³
404 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
O4	0.14160 (19)	0.29091 (17)	0.65390 (9)	0.0490 (5)
O8	0.6445 (2)	0.3074 (2)	0.65049 (10)	0.0584 (5)
O2	0.6991 (2)	−0.0498 (2)	0.13171 (10)	0.0641 (6)
O6	1.2124 (2)	−0.0612 (2)	0.13477 (10)	0.0663 (6)
C12	0.3000 (2)	0.2119 (2)	0.42976 (13)	0.0377 (6)
C15	0.1936 (2)	0.2736 (2)	0.57966 (13)	0.0368 (6)
O5	0.9275 (2)	0.3222 (2)	0.00997 (10)	0.0698 (6)
O1	0.4129 (2)	0.3330 (2)	0.00836 (10)	0.0674 (6)
C33	0.6939 (3)	0.2778 (2)	0.57720 (13)	0.0393 (6)
C29	0.8934 (3)	0.1922 (2)	0.35458 (13)	0.0413 (6)
H29	0.9886	0.1486	0.3536	0.050*
C13	0.2388 (2)	0.3479 (2)	0.44573 (13)	0.0400 (6)
H13	0.2332	0.4200	0.4055	0.048*
C11	0.3571 (3)	0.1739 (3)	0.35295 (14)	0.0444 (6)
H11	0.4007	0.0807	0.3497	0.053*
C30	0.8207 (3)	0.2192 (2)	0.43039 (13)	0.0367 (6)
C35	0.8980 (3)	0.1892 (2)	0.49504 (13)	0.0404 (6)
H35	0.9942	0.1490	0.4892	0.048*
C31	0.6761 (3)	0.2748 (2)	0.44293 (13)	0.0394 (6)
H31	0.6201	0.2922	0.4013	0.047*
C16	0.2576 (3)	0.1382 (2)	0.56550 (13)	0.0401 (6)
H16	0.2659	0.0670	0.6060	0.048*
C4	0.5278 (3)	0.1016 (3)	0.20863 (14)	0.0463 (6)
H4	0.5554	0.0505	0.2539	0.056*
C19	0.9651 (3)	0.2384 (3)	0.07433 (14)	0.0491 (7)
C24	0.8850 (3)	0.2751 (3)	0.14382 (14)	0.0436 (6)
C3	0.5943 (3)	0.0623 (3)	0.13922 (15)	0.0471 (6)
O7	0.7066 (2)	0.4560 (2)	0.19247 (11)	0.0734 (6)
C32	0.6124 (3)	0.3051 (2)	0.51476 (13)	0.0410 (6)
H32	0.5156	0.3435	0.5211	0.049*
C34	0.8365 (3)	0.2172 (3)	0.56693 (14)	0.0443 (6)
H34	0.8908	0.1954	0.6090	0.053*
C23	0.9194 (3)	0.1940 (2)	0.21264 (13)	0.0421 (6)
C20	1.0740 (3)	0.1273 (3)	0.07344 (15)	0.0522 (7)
H20	1.1262	0.1047	0.0273	0.063*
C1	0.4531 (3)	0.2517 (3)	0.07286 (14)	0.0473 (6)
C5	0.4200 (3)	0.2160 (3)	0.21234 (13)	0.0430 (6)
C2	0.5590 (3)	0.1378 (3)	0.07091 (14)	0.0516 (7)
H2	0.6062	0.1118	0.0243	0.062*
C28	0.8397 (3)	0.2227 (2)	0.28713 (14)	0.0444 (6)
H28	0.7443	0.2654	0.2869	0.053*
C21	1.1053 (3)	0.0493 (3)	0.14175 (15)	0.0481 (6)
C14	0.1858 (3)	0.3803 (2)	0.51919 (13)	0.0395 (6)
H14	0.1453	0.4726	0.5280	0.047*
C6	0.3793 (3)	0.2931 (3)	0.14320 (14)	0.0441 (6)
O3	0.1938 (3)	0.4673 (3)	0.19099 (12)	0.0913 (8)
C17	0.3091 (3)	0.1078 (2)	0.49209 (13)	0.0396 (6)
H17	0.3509	0.0157	0.4837	0.047*
C22	1.0291 (3)	0.0813 (3)	0.21013 (14)	0.0475 (6)
H22	1.0513	0.0267	0.2554	0.057*
C10	0.3540 (3)	0.2567 (3)	0.28771 (14)	0.0492 (7)
H10	0.3060	0.3484	0.2896	0.059*
C27	0.7704 (3)	0.3951 (3)	0.13975 (16)	0.0545 (7)
H27	0.7437	0.4282	0.0909	0.065*
C18	0.0775 (3)	0.4283 (3)	0.67268 (16)	0.0655 (9)
H18A	0.1483	0.4957	0.6614	0.098*
H18B	0.0444	0.4241	0.7265	0.098*
H18C	−0.0035	0.4581	0.6429	0.098*
C9	0.2627 (3)	0.4111 (3)	0.13893 (17)	0.0593 (8)
H9	0.2396	0.4467	0.0898	0.071*
C25	1.0115 (4)	0.2970 (3)	−0.06044 (15)	0.0743 (9)
H25A	1.1114	0.3084	−0.0557	0.111*
H25B	0.9758	0.3642	−0.1008	0.111*
H25C	1.0042	0.2014	−0.0725	0.111*
C8	0.7351 (4)	−0.1367 (3)	0.19987 (16)	0.0722 (9)
H8A	0.7697	−0.0791	0.2346	0.108*
H8B	0.8097	−0.2118	0.1868	0.108*
H8C	0.6502	−0.1779	0.2241	0.108*
C36	0.5076 (3)	0.3858 (3)	0.66358 (16)	0.0632 (8)
H36A	0.5030	0.4724	0.6297	0.095*
H36B	0.4933	0.4091	0.7160	0.095*
H36C	0.4329	0.3295	0.6540	0.095*
C26	1.2461 (4)	−0.1482 (3)	0.20355 (16)	0.0727 (9)
H26A	1.2762	−0.0899	0.2394	0.109*
H26B	1.3232	−0.2215	0.1914	0.109*
H26C	1.1613	−0.1917	0.2260	0.109*
C7	0.4947 (4)	0.3057 (3)	−0.06241 (15)	0.0728 (9)
H7A	0.5953	0.3159	−0.0586	0.109*
H7B	0.4589	0.3728	−0.1028	0.109*
H7C	0.4855	0.2101	−0.0738	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0641 (12)	0.0468 (10)	0.0339 (10)	0.0028 (9)	−0.0014 (9)	−0.0061 (8)
O8	0.0587 (12)	0.0752 (13)	0.0359 (11)	0.0159 (10)	−0.0024 (9)	−0.0079 (9)
O2	0.0753 (14)	0.0640 (12)	0.0428 (11)	0.0229 (11)	0.0027 (10)	0.0008 (9)
O6	0.0766 (14)	0.0687 (13)	0.0430 (11)	0.0281 (11)	0.0005 (10)	−0.0008 (9)
C12	0.0364 (13)	0.0377 (13)	0.0383 (14)	−0.0038 (10)	−0.0014 (11)	−0.0023 (10)
C15	0.0364 (13)	0.0404 (13)	0.0336 (14)	−0.0026 (11)	−0.0040 (11)	−0.0048 (10)
O5	0.0817 (14)	0.0805 (14)	0.0353 (11)	0.0236 (11)	0.0019 (10)	0.0076 (10)
O1	0.0782 (14)	0.0788 (14)	0.0348 (11)	0.0208 (11)	0.0007 (10)	0.0044 (9)
C33	0.0438 (15)	0.0380 (13)	0.0347 (14)	−0.0009 (11)	−0.0027 (11)	−0.0016 (10)
C29	0.0428 (14)	0.0406 (13)	0.0391 (15)	−0.0001 (11)	−0.0019 (12)	−0.0034 (11)
C13	0.0452 (15)	0.0379 (13)	0.0353 (14)	−0.0010 (11)	−0.0065 (11)	0.0039 (11)
C11	0.0488 (15)	0.0438 (14)	0.0392 (15)	−0.0006 (12)	−0.0005 (12)	−0.0062 (12)
C30	0.0395 (14)	0.0331 (12)	0.0371 (14)	−0.0032 (10)	−0.0033 (11)	−0.0022 (10)
C35	0.0334 (13)	0.0438 (14)	0.0440 (15)	−0.0008 (11)	−0.0076 (11)	−0.0035 (11)
C31	0.0423 (15)	0.0405 (13)	0.0350 (14)	−0.0011 (11)	−0.0105 (11)	0.0018 (10)
C16	0.0483 (15)	0.0328 (12)	0.0385 (14)	−0.0036 (11)	−0.0077 (12)	0.0028 (10)
C4	0.0518 (16)	0.0506 (15)	0.0336 (14)	0.0021 (13)	−0.0040 (12)	0.0007 (11)
C19	0.0574 (17)	0.0488 (15)	0.0383 (15)	0.0006 (13)	−0.0054 (13)	0.0030 (12)
C24	0.0491 (15)	0.0428 (14)	0.0368 (15)	0.0013 (12)	−0.0022 (12)	−0.0033 (11)
C3	0.0511 (16)	0.0482 (15)	0.0399 (15)	0.0024 (13)	−0.0018 (12)	−0.0050 (12)
O7	0.0889 (16)	0.0706 (13)	0.0507 (13)	0.0321 (12)	−0.0004 (11)	−0.0093 (10)
C32	0.0351 (14)	0.0435 (14)	0.0421 (15)	0.0026 (11)	−0.0037 (11)	−0.0012 (11)
C34	0.0406 (15)	0.0536 (15)	0.0386 (15)	0.0018 (12)	−0.0113 (12)	−0.0037 (12)
C23	0.0475 (15)	0.0406 (13)	0.0377 (14)	−0.0028 (12)	−0.0022 (12)	−0.0052 (11)
C20	0.0574 (17)	0.0561 (16)	0.0388 (16)	0.0063 (14)	0.0032 (13)	−0.0062 (13)
C1	0.0549 (16)	0.0515 (15)	0.0335 (14)	−0.0017 (13)	−0.0058 (12)	0.0026 (12)
C5	0.0472 (15)	0.0472 (14)	0.0351 (14)	−0.0050 (12)	−0.0052 (12)	−0.0047 (11)
C2	0.0611 (18)	0.0555 (16)	0.0344 (15)	0.0036 (14)	0.0016 (13)	−0.0035 (12)
C28	0.0486 (15)	0.0427 (14)	0.0403 (15)	0.0015 (12)	−0.0029 (12)	−0.0050 (11)
C21	0.0515 (16)	0.0460 (15)	0.0441 (16)	0.0047 (12)	−0.0025 (13)	−0.0051 (12)
C14	0.0439 (14)	0.0323 (12)	0.0412 (15)	0.0031 (11)	−0.0073 (11)	−0.0031 (11)
C6	0.0463 (15)	0.0476 (15)	0.0369 (15)	−0.0012 (12)	−0.0023 (12)	−0.0034 (11)
O3	0.1072 (18)	0.0979 (17)	0.0522 (14)	0.0503 (15)	0.0014 (13)	−0.0063 (12)
C17	0.0452 (14)	0.0311 (12)	0.0414 (15)	−0.0005 (10)	−0.0030 (11)	−0.0036 (10)
C22	0.0546 (16)	0.0511 (15)	0.0346 (15)	0.0019 (13)	−0.0033 (12)	−0.0035 (12)
C10	0.0545 (16)	0.0524 (15)	0.0390 (15)	0.0053 (13)	−0.0042 (12)	−0.0078 (12)
C27	0.0600 (18)	0.0560 (17)	0.0437 (16)	0.0056 (14)	−0.0046 (14)	−0.0004 (13)
C18	0.088 (2)	0.0557 (17)	0.0473 (18)	0.0156 (16)	0.0027 (16)	−0.0153 (14)
C9	0.0634 (19)	0.0636 (18)	0.0450 (17)	0.0100 (15)	0.0002 (15)	−0.0005 (14)
C25	0.091 (2)	0.086 (2)	0.0361 (17)	0.0159 (19)	0.0019 (16)	0.0065 (15)
C8	0.087 (2)	0.0664 (19)	0.0513 (19)	0.0222 (17)	−0.0011 (16)	0.0105 (15)
C36	0.0549 (18)	0.076 (2)	0.0524 (18)	0.0074 (15)	0.0112 (14)	−0.0083 (15)
C26	0.084 (2)	0.070 (2)	0.0526 (19)	0.0292 (17)	−0.0030 (16)	0.0004 (15)
C7	0.091 (2)	0.080 (2)	0.0374 (17)	0.0167 (18)	0.0009 (16)	0.0060 (15)

Geometric parameters (Å, º) top

O4—C15	1.361 (3)	C3—C2	1.380 (3)
O4—C18	1.420 (3)	O7—C27	1.206 (3)
O8—C33	1.365 (3)	C32—H32	0.9300
O8—C36	1.405 (3)	C34—H34	0.9300
O2—C3	1.360 (3)	C23—C22	1.386 (3)
O2—C8	1.426 (3)	C23—C28	1.468 (3)
O6—C21	1.362 (3)	C20—C21	1.380 (3)
O6—C26	1.430 (3)	C20—H20	0.9300
C12—C13	1.387 (3)	C1—C2	1.372 (3)
C12—C17	1.396 (3)	C1—C6	1.417 (3)
C12—C11	1.461 (3)	C5—C6	1.412 (3)
C15—C16	1.382 (3)	C5—C10	1.468 (3)
C15—C14	1.388 (3)	C2—H2	0.9300
O5—C19	1.363 (3)	C28—H28	0.9300
O5—C25	1.418 (3)	C21—C22	1.372 (3)
O1—C1	1.361 (3)	C14—H14	0.9300
O1—C7	1.418 (3)	C6—C9	1.463 (4)
C33—C32	1.382 (3)	O3—C9	1.194 (3)
C33—C34	1.383 (3)	C17—H17	0.9300
C29—C28	1.324 (3)	C22—H22	0.9300
C29—C30	1.461 (3)	C10—H10	0.9300
C29—H29	0.9300	C27—H27	0.9300
C13—C14	1.383 (3)	C18—H18A	0.9600
C13—H13	0.9300	C18—H18B	0.9600
C11—C10	1.319 (3)	C18—H18C	0.9600
C11—H11	0.9300	C9—H9	0.9300
C30—C31	1.389 (3)	C25—H25A	0.9600
C30—C35	1.392 (3)	C25—H25B	0.9600
C35—C34	1.368 (3)	C25—H25C	0.9600
C35—H35	0.9300	C8—H8A	0.9600
C31—C32	1.379 (3)	C8—H8B	0.9600
C31—H31	0.9300	C8—H8C	0.9600
C16—C17	1.374 (3)	C36—H36A	0.9600
C16—H16	0.9300	C36—H36B	0.9600
C4—C3	1.373 (3)	C36—H36C	0.9600
C4—C5	1.387 (3)	C26—H26A	0.9600
C4—H4	0.9300	C26—H26B	0.9600
C19—C20	1.371 (3)	C26—H26C	0.9600
C19—C24	1.414 (3)	C7—H7A	0.9600
C24—C23	1.407 (3)	C7—H7B	0.9600
C24—C27	1.464 (3)	C7—H7C	0.9600

C15—O4—C18	118.68 (19)	C1—C2—C3	119.0 (2)
C33—O8—C36	119.0 (2)	C1—C2—H2	120.5
C3—O2—C8	117.7 (2)	C3—C2—H2	120.5
C21—O6—C26	117.2 (2)	C29—C28—C23	124.8 (2)
C13—C12—C17	116.8 (2)	C29—C28—H28	117.6
C13—C12—C11	123.9 (2)	C23—C28—H28	117.6
C17—C12—C11	119.2 (2)	O6—C21—C22	124.1 (2)
O4—C15—C16	115.8 (2)	O6—C21—C20	114.9 (2)
O4—C15—C14	124.9 (2)	C22—C21—C20	121.0 (2)
C16—C15—C14	119.3 (2)	C13—C14—C15	119.3 (2)
C19—O5—C25	117.6 (2)	C13—C14—H14	120.4
C1—O1—C7	117.6 (2)	C15—C14—H14	120.4
O8—C33—C32	124.7 (2)	C5—C6—C1	118.2 (2)
O8—C33—C34	115.8 (2)	C5—C6—C9	124.4 (2)
C32—C33—C34	119.5 (2)	C1—C6—C9	117.4 (2)
C28—C29—C30	127.5 (2)	C16—C17—C12	121.5 (2)
C28—C29—H29	116.2	C16—C17—H17	119.2
C30—C29—H29	116.2	C12—C17—H17	119.2
C14—C13—C12	122.5 (2)	C21—C22—C23	120.9 (2)
C14—C13—H13	118.8	C21—C22—H22	119.6
C12—C13—H13	118.8	C23—C22—H22	119.6
C10—C11—C12	127.4 (2)	C11—C10—C5	125.5 (2)
C10—C11—H11	116.3	C11—C10—H10	117.3
C12—C11—H11	116.3	C5—C10—H10	117.3
C31—C30—C35	116.5 (2)	O7—C27—C24	127.4 (3)
C31—C30—C29	123.9 (2)	O7—C27—H27	116.3
C35—C30—C29	119.6 (2)	C24—C27—H27	116.3
C34—C35—C30	121.9 (2)	O4—C18—H18A	109.5
C34—C35—H35	119.0	O4—C18—H18B	109.5
C30—C35—H35	119.0	H18A—C18—H18B	109.5
C32—C31—C30	122.4 (2)	O4—C18—H18C	109.5
C32—C31—H31	118.8	H18A—C18—H18C	109.5
C30—C31—H31	118.8	H18B—C18—H18C	109.5
C17—C16—C15	120.6 (2)	O3—C9—C6	127.8 (3)
C17—C16—H16	119.7	O3—C9—H9	116.1
C15—C16—H16	119.7	C6—C9—H9	116.1
C3—C4—C5	121.1 (2)	O5—C25—H25A	109.5
C3—C4—H4	119.4	O5—C25—H25B	109.5
C5—C4—H4	119.4	H25A—C25—H25B	109.5
O5—C19—C20	123.4 (2)	O5—C25—H25C	109.5
O5—C19—C24	115.3 (2)	H25A—C25—H25C	109.5
C20—C19—C24	121.3 (2)	H25B—C25—H25C	109.5
C23—C24—C19	118.3 (2)	O2—C8—H8A	109.5
C23—C24—C27	123.8 (2)	O2—C8—H8B	109.5
C19—C24—C27	117.9 (2)	H8A—C8—H8B	109.5
O2—C3—C4	123.9 (2)	O2—C8—H8C	109.5
O2—C3—C2	114.9 (2)	H8A—C8—H8C	109.5
C4—C3—C2	121.1 (2)	H8B—C8—H8C	109.5
C31—C32—C33	119.3 (2)	O8—C36—H36A	109.5
C31—C32—H32	120.3	O8—C36—H36B	109.5
C33—C32—H32	120.3	H36A—C36—H36B	109.5
C35—C34—C33	120.2 (2)	O8—C36—H36C	109.5
C35—C34—H34	119.9	H36A—C36—H36C	109.5
C33—C34—H34	119.9	H36B—C36—H36C	109.5
C22—C23—C24	119.3 (2)	O6—C26—H26A	109.5
C22—C23—C28	118.8 (2)	O6—C26—H26B	109.5
C24—C23—C28	121.9 (2)	H26A—C26—H26B	109.5
C19—C20—C21	119.2 (2)	O6—C26—H26C	109.5
C19—C20—H20	120.4	H26A—C26—H26C	109.5
C21—C20—H20	120.4	H26B—C26—H26C	109.5
O1—C1—C2	122.8 (2)	O1—C7—H7A	109.5
O1—C1—C6	115.6 (2)	O1—C7—H7B	109.5
C2—C1—C6	121.5 (2)	H7A—C7—H7B	109.5
C4—C5—C6	119.0 (2)	O1—C7—H7C	109.5
C4—C5—C10	119.5 (2)	H7A—C7—H7C	109.5
C6—C5—C10	121.6 (2)	H7B—C7—H7C	109.5

C18—O4—C15—C16	178.6 (2)	C7—O1—C1—C6	173.1 (2)
C18—O4—C15—C14	−1.7 (3)	C3—C4—C5—C6	−0.2 (4)
C36—O8—C33—C32	−7.7 (4)	C3—C4—C5—C10	−178.5 (2)
C36—O8—C33—C34	171.8 (2)	O1—C1—C2—C3	179.1 (2)
C17—C12—C13—C14	−1.4 (3)	C6—C1—C2—C3	−0.2 (4)
C11—C12—C13—C14	−179.9 (2)	O2—C3—C2—C1	179.2 (2)
C13—C12—C11—C10	−3.6 (4)	C4—C3—C2—C1	−1.5 (4)
C17—C12—C11—C10	177.9 (2)	C30—C29—C28—C23	179.3 (2)
C28—C29—C30—C31	4.4 (4)	C22—C23—C28—C29	27.9 (4)
C28—C29—C30—C35	−175.4 (2)	C24—C23—C28—C29	−153.8 (2)
C31—C30—C35—C34	−2.1 (3)	C26—O6—C21—C22	0.1 (4)
C29—C30—C35—C34	177.7 (2)	C26—O6—C21—C20	−178.1 (3)
C35—C30—C31—C32	2.7 (3)	C19—C20—C21—O6	178.3 (2)
C29—C30—C31—C32	−177.0 (2)	C19—C20—C21—C22	0.1 (4)
O4—C15—C16—C17	177.7 (2)	C12—C13—C14—C15	0.0 (4)
C14—C15—C16—C17	−2.0 (3)	O4—C15—C14—C13	−178.0 (2)
C25—O5—C19—C20	−3.6 (4)	C16—C15—C14—C13	1.7 (3)
C25—O5—C19—C24	175.3 (2)	C4—C5—C6—C1	−1.4 (4)
O5—C19—C24—C23	−179.3 (2)	C10—C5—C6—C1	176.9 (2)
C20—C19—C24—C23	−0.3 (4)	C4—C5—C6—C9	176.9 (2)
O5—C19—C24—C27	1.1 (4)	C10—C5—C6—C9	−4.8 (4)
C20—C19—C24—C27	−179.9 (2)	O1—C1—C6—C5	−177.7 (2)
C8—O2—C3—C4	4.0 (4)	C2—C1—C6—C5	1.6 (4)
C8—O2—C3—C2	−176.8 (3)	O1—C1—C6—C9	3.8 (4)
C5—C4—C3—O2	−179.1 (2)	C2—C1—C6—C9	−176.8 (2)
C5—C4—C3—C2	1.7 (4)	C15—C16—C17—C12	0.6 (4)
C30—C31—C32—C33	−0.9 (3)	C13—C12—C17—C16	1.0 (3)
O8—C33—C32—C31	177.8 (2)	C11—C12—C17—C16	179.7 (2)
C34—C33—C32—C31	−1.7 (3)	O6—C21—C22—C23	−178.8 (2)
C30—C35—C34—C33	−0.4 (4)	C20—C21—C22—C23	−0.7 (4)
O8—C33—C34—C35	−177.2 (2)	C24—C23—C22—C21	0.8 (4)
C32—C33—C34—C35	2.3 (4)	C28—C23—C22—C21	179.1 (2)
C19—C24—C23—C22	−0.3 (4)	C12—C11—C10—C5	176.5 (2)
C27—C24—C23—C22	179.3 (2)	C4—C5—C10—C11	−19.5 (4)
C19—C24—C23—C28	−178.6 (2)	C6—C5—C10—C11	162.3 (3)
C27—C24—C23—C28	1.0 (4)	C23—C24—C27—O7	12.8 (5)
O5—C19—C20—C21	179.3 (3)	C19—C24—C27—O7	−167.6 (3)
C24—C19—C20—C21	0.4 (4)	C5—C6—C9—O3	6.5 (5)
C7—O1—C1—C2	−6.2 (4)	C1—C6—C9—O3	−175.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C12–C17 and C30–C35 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.29	2.681 (4)	105
C10—H10···O3	0.93	2.25	2.863 (4)	123
C27—H27···O5	0.93	2.31	2.681 (4)	103
C28—H28···O7	0.93	2.34	2.861 (3)	115
C14—H14···Cg4ⁱ	0.93	2.88	3.597 (3)	135
C17—H14···Cg4ⁱⁱ	0.93	2.76	3.471 (3)	134
C32—H14···Cg2	0.93	2.82	3.530 (3)	135
C15—H14···Cg2ⁱⁱⁱ	0.93	2.66	3.371 (3)	134

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₄
M_r	298.32
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.292 (5), 9.448 (5), 17.547 (5)
α, β, γ (°)	84.097 (5), 84.040 (5), 83.315 (5)
V (Å³)	1515.3 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	10535, 5272, 3060
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.168, 0.79
No. of reflections	5272
No. of parameters	404
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C12–C17 and C30–C35 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg4ⁱ	0.93	2.88	3.597 (3)	135
C17—H14···Cg4ⁱⁱ	0.93	2.76	3.471 (3)	134
C32—H14···Cg2	0.93	2.82	3.530 (3)	135
C15—H14···Cg2ⁱⁱⁱ	0.93	2.66	3.371 (3)	134

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

Acknowledgements

This work was supported by Anhui Provincial Natural Science Foundation (grant No. 1308085MB18).

References

Boumendjel, A., Boccard, J., Carrupt, P. A., Nicolle, E., Blanc, M., Geze, A., Choisnard, L., Wouessidjewe, D., Matera, E. L. & Dumontet, C. (2008). J. Med. Chem. 51, 2307–2310. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, X. F., Ruan, B. F., Wang, X. T., Xu, C., Ge, H. M., Zhu, H. L. & Tan, R. X. (2007). Eur. J. Med. Chem. 42, 263–267. Web of Science CrossRef PubMed CAS Google Scholar
Jang, M., Cai, L., Udeani, G. O., Slowing, K. V., Thomas, C. F., Beecher, C. W. W., Fong, H. H. S., Farnworth, R. N., Kinghorn, A. D., Metha, R. G., Moon, R. C. & Pezzuto, J. M. (1997). Science, 275, 218–220. CrossRef CAS PubMed Web of Science Google Scholar
Orsini, F., Pelizzoni, F., Verotta, L. & Aburjai, T. (1997). J. Nat. Prod. 60, 1082–1087. CrossRef CAS PubMed Web of Science Google Scholar
Pettit, G. R., Grealish, M. P., Jung, M. K., Hamel, E., Pettit, R. K., Chapuis, J. C. & Schmidt, J. M. (2002). J. Med. Chem. 45, 2534–2542. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o629

https://doi.org/10.1107/S1600536813007964

Open

access