(E)-3-(8-Benz­yloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hy­droxy-4,6-bis­(meth­oxy­meth­oxy)phen­yl]prop-2-en-1-one

Zhang, Y.; Zhang, Y.-N.; Liu, M.-M.; Ryu, K.-C.; Ye, D.-Y.

doi:10.1107/S160053681100924X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o912-o913

doi:10.1107/S160053681100924X

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(E)-3-(8-Benzyloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one

Yu Zhang,^a Yi-Nan Zhang,^a Ming-Ming Liu,^a Kum-Chol Ryu ^b and De-Yong Ye ^a ^*

^aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, People's Republic of China, and ^bInstitute of Pharmacy, Ham Hung Pharmaceutical University, Ham Hung, Democratic People's Republic of Korea
^*Correspondence e-mail: dyye@shmu.edu.cn

(Received 6 March 2011; accepted 10 March 2011; online 19 March 2011)

In the title molecule, C₂₈H₂₈O₉, the phenol and the benzene rings adjacent to the α,β-unsaturated ketone unit are inclined at 9.15 (13)° to each other. The terminal phenyl ring is oriented with respect to the phenol ring at a dihedral angle of 85.88 (13)°. In the crystal, the methylene C atoms of the dihydrodioxine ring are disordered over two sites with an occupancy ratio of 0.463 (18):0.537 (18), and both disordered components of the dihydrodioxine ring adopt twisted-chair conformations. An intramolecular O—H⋯O hydrogen bond and weak intermolecular C—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For background to 1,3-diaryl-2-propen-1-one, see: Carlo et al. (1999 ); Dimmock et al. (1999 ); Go et al. (2005 ); Nowakowska (2007 ); Yarishkin et al. (2008 ). For related structures, see: Özbey et al. (1997 ); Gao & Ng (2006 ); Loghmani-Khouzani et al. (2009 ); Rizvi et al. (2010 ). For the synthesis, see: Lin et al. (2007 ).

Experimental

Crystal data

C₂₈H₂₈O₉
M_r = 508.50
Triclinic, $[P \overline 1]$
a = 8.149 (4) Å
b = 11.744 (5) Å
c = 14.439 (7) Å
α = 72.752 (5)°
β = 84.269 (5)°
γ = 70.601 (5)°
V = 1244.7 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.35 × 0.25 × 0.18 mm

Data collection

Bruker CCD 1000 area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.982
5687 measured reflections
4774 independent reflections
3239 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.195
S = 1.02
4774 reflections
353 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9C⋯O4	0.82	1.71	2.448 (2)	149
C6—H6A⋯O9ⁱ	0.93	2.57	3.426 (3)	154
C21—H21A⋯O8ⁱⁱ	0.93	2.53	3.453 (3)	169
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x-1, -y+3, -z+1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100924X/xu5171sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100924X/xu5171Isup2.hkl

checkCIF report

Comment top

1,3-Diaryl-2-propen-1-ones, commonly known as chalcones are a kind of aromatic ketones that form the central core for a variety of important biological compounds, showing anti-bacterial, anti-fungal, anti-malarial, anti-viral, anti-inflammatory, anti-oxidant and anti-tumor properties, which have been reviewed by Carlo et al. (1999), Dimmock et al. (1999), Go et al. (2005) and Nowakowska (2007). Some even demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). Chalcones can also be converted into flavonoids in several classical synthetic steps, consolidating its significance in synthetic chemistry.

The title compound, i.e. (E)-3-(8-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl) -1-(2-hydroxy-4,6-bis(methoxymethyl)phenyl)prop-2-en-1-one, is first prepared aiming to find out potential anti-virus candidates. It is obtained from a dihydrobenzo[b][1,4]dioxine aldehyde derivative and an acetophenone derivative by a classical aldol condensation in the presence of potassium hydroxide as a catalyst (Lin et al., 2007). We now report here the synthesis and crystal structure, as part of our investigations in revealing the relationship between the structure and the anti-virus activity. A series of chalcones related to the title compound is also under investigation for their biological activities in our laboratory.

The title molecule is presented in Fig. 1. The least-square planes of the benzene and phenol rings defined by atoms C3—C8 and C19—C24, respectively, are inclined at 9.15 (13)° with respect to each other. The dihedral angle between the benzyloxy group and the benzene plane is 85.90 (7)°. Both the major and minor conformers of the disordered dioxane ring adopt twist-chair conformations [ϕ = 193.86 (8)°, θ = 77.63 (16)° (for ring C1—C2—O2—C3—C4—O1), and ϕ = 184.02 (10)°, θ = 95.1 (2)° (for ring C1'-C2'-O2—C3—C4—O1)], having total puckering amplitudes, Q_T, of 0.2538 (8) Å and 0.1675 (10) Å, respectively. The crystal structure is stabilized by a strong intramolecular O—H···O hydrogen bond, and further consolidated by the weak intermolecular hydrogen-bonding interactions of the type C—H···O, and Van der Waals forces (Table 1).

Related literature top

For background to 1,3-diaryl-2-propen-1-one, see: Carlo et al. (1999); Dimmock et al. (1999); Go et al. (2005); Nowakowska (2007); Yarishkin et al. (2008). For related structures, see: Özbey et al. (1997); Gao et al. (2006); Loghmani-Khouzani et al. (2009); Rizvi et al. (2010). For the synthesis, see: Lin et al. (2007).

Experimental top

1-[2-Hydroxy-4,6-bis-(methoxymethyl)-phenyl]-ethanone (1.8 g, 7.0 mmol) and 8-(benzyloxy)-2,3-dihydro-benzo[b][1,4]dioxine-6-carbaldehyde (1.9 g, 7.0 mmol) were dissolved in 95% EtOH, KOH/H₂O solution (3M). The reaction mixture was stirred at room temperature overnight, evaporated under reduced pressure, and further extracted by ethyl acetate. The extract layer was chromatographed on silica gel to afford the title compound (3.2 g, yield 90%) as an orange solid. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate and petroleum ether solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 title compound. The displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

(E)-3-(8-Benzyloxy-2,3-dihydro-1,4-benzodioxin-6-yl)- 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one top

Crystal data top

C₂₈H₂₈O₉	Z = 2
M_r = 508.50	F(000) = 536
Triclinic, P1	D_x = 1.357 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.149 (4) Å	Cell parameters from 847 reflections
b = 11.744 (5) Å	θ = 2.7–27.1°
c = 14.439 (7) Å	µ = 0.10 mm⁻¹
α = 72.752 (5)°	T = 294 K
β = 84.269 (5)°	Block, orange
γ = 70.601 (5)°	0.35 × 0.25 × 0.18 mm
V = 1244.7 (10) Å³

Data collection top

Bruker CCD 1000 area-detector diffractometer	4774 independent reflections
Radiation source: sealed tube	3239 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.965, T_max = 0.982	k = −14→12
5687 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.126P)²] where P = (F_o² + 2F_c²)/3
4774 reflections	(Δ/σ)_max < 0.001
353 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₈H₂₈O₉	γ = 70.601 (5)°
M_r = 508.50	V = 1244.7 (10) Å³
Triclinic, P1	Z = 2
a = 8.149 (4) Å	Mo Kα radiation
b = 11.744 (5) Å	µ = 0.10 mm⁻¹
c = 14.439 (7) Å	T = 294 K
α = 72.752 (5)°	0.35 × 0.25 × 0.18 mm
β = 84.269 (5)°

Data collection top

Bruker CCD 1000 area-detector diffractometer	4774 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3239 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.982	R_int = 0.026
5687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.02	Δρ_max = 0.60 e Å⁻³
4774 reflections	Δρ_min = −0.21 e Å⁻³
353 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	Occ. (<1)
O1	−0.02313 (19)	0.61404 (14)	0.91280 (12)	0.0582 (5)
O2	−0.2521 (2)	0.86192 (14)	0.83479 (12)	0.0597 (5)
O3	0.29103 (19)	0.54252 (13)	0.84269 (11)	0.0558 (5)
O4	0.3240 (2)	1.09630 (15)	0.44508 (13)	0.0642 (5)
O5	−0.1587 (2)	1.65623 (15)	0.28563 (12)	0.0647 (5)
O6	−0.2044 (3)	1.83191 (15)	0.15912 (13)	0.0736 (5)
O7	−0.1328 (2)	1.30029 (15)	0.55058 (12)	0.0659 (5)
O8	−0.4304 (3)	1.35542 (18)	0.53966 (16)	0.0848 (6)
O9	0.3228 (2)	1.28722 (16)	0.31656 (13)	0.0668 (5)
H9C	0.3572	1.2137	0.3494	0.100*
C1	−0.172 (2)	0.6699 (16)	0.9639 (10)	0.086 (4)	0.463 (18)
H1A	−0.2494	0.6200	0.9719	0.103*	0.463 (18)
H1B	−0.1333	0.6586	1.0283	0.103*	0.463 (18)
C2	−0.2644 (15)	0.7837 (9)	0.9331 (7)	0.057 (2)	0.463 (18)
H2A	−0.2440	0.8268	0.9765	0.069*	0.463 (18)
H2B	−0.3847	0.7855	0.9424	0.069*	0.463 (18)
C1'	−0.2038 (13)	0.6528 (9)	0.9316 (8)	0.054 (2)	0.537 (18)
H1'1	−0.2492	0.5982	0.9103	0.065*	0.537 (18)
H1'2	−0.2150	0.6304	1.0017	0.065*	0.537 (18)
C2'	−0.3120 (14)	0.7637 (13)	0.9008 (13)	0.110 (5)	0.537 (18)
H2'1	−0.3615	0.7923	0.9570	0.132*	0.537 (18)
H2'2	−0.4062	0.7567	0.8690	0.132*	0.537 (18)
C3	−0.0883 (3)	0.82076 (19)	0.79882 (16)	0.0448 (5)
C4	0.0230 (3)	0.69963 (18)	0.83660 (15)	0.0443 (5)
C5	0.1907 (3)	0.66401 (18)	0.79889 (16)	0.0451 (5)
C6	0.2440 (3)	0.74792 (19)	0.72391 (16)	0.0474 (5)
H6A	0.3559	0.7236	0.6991	0.057*
C7	0.1314 (3)	0.86943 (18)	0.68465 (15)	0.0432 (5)
C8	−0.0349 (3)	0.90484 (19)	0.72278 (16)	0.0458 (5)
H8A	−0.1109	0.9854	0.6971	0.055*
C9	0.4658 (3)	0.5063 (2)	0.8107 (2)	0.0668 (7)
H9A	0.5240	0.5615	0.8209	0.080*
H9B	0.4686	0.5137	0.7419	0.080*
C10	0.5581 (3)	0.3732 (2)	0.86577 (16)	0.0493 (6)
C11	0.5419 (3)	0.2761 (2)	0.83868 (17)	0.0581 (6)
H11A	0.4675	0.2931	0.7880	0.070*
C12	0.6339 (4)	0.1524 (2)	0.8848 (2)	0.0697 (7)
H12A	0.6209	0.0874	0.8651	0.084*
C13	0.7425 (4)	0.1264 (2)	0.9585 (2)	0.0699 (8)
H13A	0.8061	0.0434	0.9885	0.084*
C14	0.7594 (4)	0.2206 (3)	0.9891 (2)	0.0758 (8)
H14A	0.8328	0.2021	1.0406	0.091*
C15	0.6664 (3)	0.3454 (2)	0.9430 (2)	0.0663 (7)
H15A	0.6772	0.4100	0.9642	0.080*
C16	0.1943 (3)	0.95607 (19)	0.60541 (15)	0.0453 (5)
H16A	0.3115	0.9287	0.5893	0.054*
C17	0.1011 (3)	1.06911 (19)	0.55476 (16)	0.0478 (5)
H17A	−0.0167	1.0994	0.5686	0.057*
C18	0.1795 (3)	1.1487 (2)	0.47661 (16)	0.0458 (5)
C19	0.0915 (3)	1.28298 (19)	0.43388 (15)	0.0431 (5)
C20	−0.0676 (3)	1.35676 (19)	0.46461 (15)	0.0461 (5)
C21	−0.1479 (3)	1.4795 (2)	0.41326 (16)	0.0510 (6)
H21A	−0.2552	1.5247	0.4335	0.061*
C22	−0.0687 (3)	1.53574 (19)	0.33120 (16)	0.0487 (5)
C23	0.0905 (3)	1.4708 (2)	0.30072 (16)	0.0528 (6)
H23A	0.1448	1.5100	0.2470	0.063*
C24	0.1693 (3)	1.3463 (2)	0.35090 (15)	0.0473 (5)
C25	−0.0851 (4)	1.7180 (3)	0.19855 (19)	0.0734 (8)
H25A	0.0211	1.7290	0.2134	0.088*
H25B	−0.0575	1.6677	0.1531	0.088*
C26	−0.2259 (6)	1.9197 (3)	0.2108 (3)	0.1194 (14)
H26A	−0.3122	1.9971	0.1795	0.179*
H26B	−0.1174	1.9344	0.2126	0.179*
H26C	−0.2627	1.8876	0.2758	0.179*
C27	−0.2982 (3)	1.3618 (2)	0.5841 (2)	0.0680 (7)
H27A	−0.3059	1.3242	0.6533	0.082*
H27B	−0.3094	1.4495	0.5740	0.082*
C28	−0.4456 (5)	1.2299 (3)	0.5652 (3)	0.0982 (11)
H28A	−0.5417	1.2315	0.5308	0.147*
H28B	−0.4649	1.2023	0.6337	0.147*
H28C	−0.3402	1.1729	0.5478	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0523 (10)	0.0408 (9)	0.0614 (10)	−0.0101 (7)	0.0183 (7)	0.0037 (7)
O2	0.0496 (9)	0.0402 (9)	0.0694 (11)	−0.0047 (7)	0.0203 (8)	−0.0036 (7)
O3	0.0429 (9)	0.0350 (8)	0.0643 (10)	−0.0012 (6)	0.0149 (7)	0.0053 (7)
O4	0.0442 (9)	0.0503 (10)	0.0700 (11)	−0.0021 (7)	0.0110 (8)	0.0056 (8)
O5	0.0641 (11)	0.0434 (9)	0.0637 (11)	−0.0075 (8)	0.0032 (8)	0.0065 (8)
O6	0.0993 (15)	0.0432 (10)	0.0642 (11)	−0.0155 (9)	−0.0202 (10)	0.0038 (8)
O7	0.0589 (10)	0.0522 (10)	0.0613 (10)	−0.0085 (8)	0.0240 (8)	0.0028 (8)
O8	0.0620 (12)	0.0685 (13)	0.1118 (17)	−0.0101 (10)	0.0126 (11)	−0.0240 (12)
O9	0.0468 (10)	0.0562 (10)	0.0720 (11)	−0.0076 (8)	0.0192 (8)	0.0028 (8)
C1	0.064 (7)	0.089 (8)	0.065 (7)	−0.001 (5)	0.024 (5)	0.003 (5)
C2	0.043 (5)	0.047 (4)	0.061 (5)	−0.006 (3)	0.025 (3)	−0.003 (3)
C1'	0.042 (3)	0.043 (3)	0.060 (5)	−0.013 (2)	0.016 (4)	0.007 (3)
C2'	0.053 (5)	0.092 (7)	0.125 (10)	−0.012 (4)	0.027 (5)	0.036 (7)
C3	0.0383 (11)	0.0347 (11)	0.0536 (13)	−0.0068 (9)	0.0085 (9)	−0.0094 (9)
C4	0.0463 (12)	0.0347 (11)	0.0464 (12)	−0.0138 (9)	0.0078 (9)	−0.0051 (9)
C5	0.0432 (12)	0.0310 (10)	0.0515 (13)	−0.0066 (9)	0.0063 (9)	−0.0054 (9)
C6	0.0399 (11)	0.0366 (11)	0.0544 (13)	−0.0068 (9)	0.0099 (9)	−0.0056 (9)
C7	0.0433 (12)	0.0352 (11)	0.0464 (12)	−0.0114 (9)	0.0033 (9)	−0.0067 (9)
C8	0.0437 (12)	0.0295 (10)	0.0533 (13)	−0.0056 (9)	0.0052 (9)	−0.0041 (9)
C9	0.0472 (14)	0.0437 (13)	0.0808 (18)	−0.0031 (11)	0.0211 (12)	0.0047 (12)
C10	0.0377 (11)	0.0393 (12)	0.0558 (14)	−0.0047 (9)	0.0124 (10)	−0.0038 (10)
C11	0.0586 (15)	0.0560 (15)	0.0532 (14)	−0.0139 (12)	0.0013 (11)	−0.0113 (11)
C12	0.083 (2)	0.0442 (14)	0.0769 (18)	−0.0134 (13)	0.0072 (15)	−0.0205 (13)
C13	0.0599 (16)	0.0448 (14)	0.0790 (19)	0.0017 (12)	0.0042 (14)	−0.0014 (13)
C14	0.0631 (18)	0.077 (2)	0.0727 (18)	−0.0190 (15)	−0.0193 (14)	0.0036 (15)
C15	0.0725 (18)	0.0574 (16)	0.0744 (18)	−0.0275 (13)	0.0030 (14)	−0.0194 (13)
C16	0.0419 (12)	0.0372 (11)	0.0493 (13)	−0.0102 (9)	0.0057 (9)	−0.0056 (9)
C17	0.0381 (11)	0.0385 (11)	0.0556 (13)	−0.0096 (9)	0.0052 (9)	−0.0011 (10)
C18	0.0373 (11)	0.0435 (12)	0.0479 (12)	−0.0107 (9)	0.0007 (9)	−0.0031 (9)
C19	0.0356 (11)	0.0407 (11)	0.0451 (12)	−0.0105 (9)	0.0012 (9)	−0.0030 (9)
C20	0.0430 (12)	0.0420 (12)	0.0461 (12)	−0.0138 (9)	0.0065 (9)	−0.0037 (9)
C21	0.0439 (12)	0.0424 (12)	0.0542 (14)	−0.0050 (10)	0.0072 (10)	−0.0074 (10)
C22	0.0504 (13)	0.0365 (11)	0.0495 (13)	−0.0112 (10)	−0.0042 (10)	0.0003 (9)
C23	0.0500 (13)	0.0469 (13)	0.0483 (13)	−0.0153 (11)	0.0071 (10)	0.0035 (10)
C24	0.0389 (12)	0.0475 (13)	0.0492 (13)	−0.0153 (10)	0.0058 (9)	−0.0047 (10)
C25	0.0837 (19)	0.0560 (16)	0.0585 (16)	−0.0155 (14)	−0.0043 (13)	0.0096 (12)
C26	0.211 (5)	0.061 (2)	0.090 (2)	−0.051 (2)	−0.006 (3)	−0.0159 (18)
C27	0.0657 (18)	0.0594 (16)	0.0700 (17)	−0.0178 (13)	0.0291 (14)	−0.0172 (13)
C28	0.090 (2)	0.082 (2)	0.130 (3)	−0.0292 (18)	0.019 (2)	−0.044 (2)

Geometric parameters (Å, º) top

O1—C4	1.369 (2)	C9—C10	1.497 (3)
O1—C1'	1.413 (10)	C9—H9A	0.9700
O1—C1	1.425 (14)	C9—H9B	0.9700
O2—C3	1.366 (2)	C10—C11	1.358 (3)
O2—C2'	1.452 (11)	C10—C15	1.384 (3)
O2—C2	1.458 (10)	C11—C12	1.385 (3)
O3—C5	1.377 (2)	C11—H11A	0.9300
O3—C9	1.416 (3)	C12—C13	1.350 (4)
O4—C18	1.245 (2)	C12—H12A	0.9300
O5—C22	1.352 (3)	C13—C14	1.357 (4)
O5—C25	1.437 (3)	C13—H13A	0.9300
O6—C25	1.362 (3)	C14—C15	1.396 (4)
O6—C26	1.400 (4)	C14—H14A	0.9300
O7—C20	1.370 (2)	C15—H15A	0.9300
O7—C27	1.415 (3)	C16—C17	1.319 (3)
O8—C27	1.341 (3)	C16—H16A	0.9300
O8—C28	1.455 (4)	C17—C18	1.477 (3)
O9—C24	1.340 (2)	C17—H17A	0.9300
O9—H9C	0.8200	C18—C19	1.464 (3)
C1—C2	1.264 (19)	C19—C20	1.413 (3)
C1—H1A	0.9700	C19—C24	1.422 (3)
C1—H1B	0.9700	C20—C21	1.375 (3)
C2—H2A	0.9700	C21—C22	1.387 (3)
C2—H2B	0.9700	C21—H21A	0.9300
C1'—C2'	1.282 (15)	C22—C23	1.373 (3)
C1'—H1'1	0.9700	C23—C24	1.384 (3)
C1'—H1'2	0.9700	C23—H23A	0.9300
C2'—H2'1	0.9700	C25—H25A	0.9700
C2'—H2'2	0.9700	C25—H25B	0.9700
C3—C8	1.384 (3)	C26—H26A	0.9600
C3—C4	1.388 (3)	C26—H26B	0.9600
C4—C5	1.395 (3)	C26—H26C	0.9600
C5—C6	1.374 (3)	C27—H27A	0.9700
C6—C7	1.398 (3)	C27—H27B	0.9700
C6—H6A	0.9300	C28—H28A	0.9600
C7—C8	1.388 (3)	C28—H28B	0.9600
C7—C16	1.465 (3)	C28—H28C	0.9600
C8—H8A	0.9300

C4—O1—C1'	112.0 (4)	C12—C11—H11A	119.3
C4—O1—C1	113.1 (6)	C13—C12—C11	119.9 (2)
C1'—O1—C1	26.9 (7)	C13—C12—H12A	120.0
C3—O2—C2'	114.7 (5)	C11—C12—H12A	120.0
C3—O2—C2	110.1 (5)	C12—C13—C14	120.4 (3)
C2'—O2—C2	30.5 (7)	C12—C13—H13A	119.8
C5—O3—C9	116.05 (16)	C14—C13—H13A	119.8
C22—O5—C25	117.68 (19)	C13—C14—C15	119.8 (3)
C25—O6—C26	113.9 (3)	C13—C14—H14A	120.1
C20—O7—C27	120.56 (18)	C15—C14—H14A	120.1
C27—O8—C28	113.5 (2)	C10—C15—C14	120.2 (2)
C24—O9—H9C	109.5	C10—C15—H15A	119.9
C2—C1—O1	122.3 (10)	C14—C15—H15A	119.9
C2—C1—H1A	106.8	C17—C16—C7	126.4 (2)
O1—C1—H1A	106.8	C17—C16—H16A	116.8
C2—C1—H1B	106.8	C7—C16—H16A	116.8
O1—C1—H1B	106.8	C16—C17—C18	121.5 (2)
H1A—C1—H1B	106.6	C16—C17—H17A	119.2
C1—C2—O2	123.6 (9)	C18—C17—H17A	119.2
C1—C2—H2A	106.4	O4—C18—C19	119.96 (18)
O2—C2—H2A	106.4	O4—C18—C17	117.31 (19)
C1—C2—H2B	106.4	C19—C18—C17	122.70 (18)
O2—C2—H2B	106.4	C20—C19—C24	115.78 (19)
H2A—C2—H2B	106.5	C20—C19—C18	126.62 (18)
C2'—C1'—O1	126.8 (8)	C24—C19—C18	117.56 (18)
C2'—C1'—H1'1	105.6	O7—C20—C21	122.18 (19)
O1—C1'—H1'1	105.6	O7—C20—C19	115.90 (18)
C2'—C1'—H1'2	105.6	C21—C20—C19	121.86 (19)
O1—C1'—H1'2	105.6	C20—C21—C22	119.9 (2)
H1'1—C1'—H1'2	106.1	C20—C21—H21A	120.0
C1'—C2'—O2	119.3 (8)	C22—C21—H21A	120.0
C1'—C2'—H2'1	107.5	O5—C22—C23	123.9 (2)
O2—C2'—H2'1	107.5	O5—C22—C21	115.3 (2)
C1'—C2'—H2'2	107.5	C23—C22—C21	120.8 (2)
O2—C2'—H2'2	107.5	C22—C23—C24	119.27 (19)
H2'1—C2'—H2'2	107.0	C22—C23—H23A	120.4
O2—C3—C8	117.66 (18)	C24—C23—H23A	120.4
O2—C3—C4	122.02 (18)	O9—C24—C23	116.51 (18)
C8—C3—C4	120.32 (18)	O9—C24—C19	121.29 (19)
O1—C4—C3	122.35 (18)	C23—C24—C19	122.19 (19)
O1—C4—C5	118.11 (18)	O6—C25—O5	107.9 (2)
C3—C4—C5	119.49 (18)	O6—C25—H25A	110.1
C6—C5—O3	125.25 (18)	O5—C25—H25A	110.1
C6—C5—C4	120.08 (19)	O6—C25—H25B	110.1
O3—C5—C4	114.67 (17)	O5—C25—H25B	110.1
C5—C6—C7	120.63 (19)	H25A—C25—H25B	108.4
C5—C6—H6A	119.7	O6—C26—H26A	109.5
C7—C6—H6A	119.7	O6—C26—H26B	109.5
C8—C7—C6	119.15 (18)	H26A—C26—H26B	109.5
C8—C7—C16	122.12 (19)	O6—C26—H26C	109.5
C6—C7—C16	118.73 (19)	H26A—C26—H26C	109.5
C3—C8—C7	120.32 (19)	H26B—C26—H26C	109.5
C3—C8—H8A	119.8	O8—C27—O7	113.2 (2)
C7—C8—H8A	119.8	O8—C27—H27A	108.9
O3—C9—C10	109.76 (17)	O7—C27—H27A	108.9
O3—C9—H9A	109.7	O8—C27—H27B	108.9
C10—C9—H9A	109.7	O7—C27—H27B	108.9
O3—C9—H9B	109.7	H27A—C27—H27B	107.8
C10—C9—H9B	109.7	O8—C28—H28A	109.5
H9A—C9—H9B	108.2	O8—C28—H28B	109.5
C11—C10—C15	118.2 (2)	H28A—C28—H28B	109.5
C11—C10—C9	120.4 (2)	O8—C28—H28C	109.5
C15—C10—C9	121.4 (2)	H28A—C28—H28C	109.5
C10—C11—C12	121.4 (3)	H28B—C28—H28C	109.5
C10—C11—H11A	119.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9C···O4	0.82	1.71	2.448 (2)	149
C6—H6A···O9ⁱ	0.93	2.57	3.426 (3)	154
C21—H21A···O8ⁱⁱ	0.93	2.53	3.453 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈O₉
M_r	508.50
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	8.149 (4), 11.744 (5), 14.439 (7)
α, β, γ (°)	72.752 (5), 84.269 (5), 70.601 (5)
V (Å³)	1244.7 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.25 × 0.18

Data collection
Diffractometer	Bruker CCD 1000 area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	5687, 4774, 3239
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.195, 1.02
No. of reflections	4774
No. of parameters	353
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.21

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9C···O4	0.82	1.71	2.448 (2)	149
C6—H6A···O9ⁱ	0.93	2.57	3.426 (3)	154
C21—H21A···O8ⁱⁱ	0.93	2.53	3.453 (3)	169

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

Acknowledgements

The authors greatly appreciate financial support from the Open Grant of the Institute of Bioscience, Fudan University, China.

References

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Volume 67| Part 4| April 2011| Pages o912-o913

doi:10.1107/S160053681100924X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-3-(8-Benz­yl­oxy-2,3-di­hydro-1,4-benzodioxin-6-yl)-1-[2-hy­dr­oxy-4,6-bis­­(meth­­oxy­meth­­oxy)phen­yl]prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-3-(8-Benzyloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one