(E)-3-[3,4-Bis(meth­oxy­methoxy)phen­yl]-1-(7-hy­droxy-5-meth­oxy-2,2-dimethyl­chroman-8-yl)prop-2-en-1-one

Hashim, N.A.; Ahmad, F.; Basar, N.; Awang, K.; Ng, S.W.

doi:10.1107/S160053681103131X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2300

doi:10.1107/S160053681103131X

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(E)-3-[3,4-Bis(methoxymethoxy)phenyl]-1-(7-hydroxy-5-methoxy-2,2-dimethylchroman-8-yl)prop-2-en-1-one

Nur Athirah Hashim,^a Farediah Ahmad,^a Norazah Basar,^a Khalijah Awang ^b and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 August 2011; accepted 3 August 2011; online 11 August 2011)

The reaction of 5,6-(2,2-dimethylchromanyl)-2-hydroxy-4-methoxyacetophenone and 3,4-bis(methoxymethyloxy)benzaldehyde affords the intense orange title chalcone derivative, C₂₅H₃₀O₈. The two benzene rings are connected through a —C(=O)—CH=CH— (propenone) unit, which is in an E conformation; the ring with the hydroxy substitutent is aligned at 19.5 (2)° with respect to this unit, whereas the ring with the methoxymethyloxy substituent is aligned at 9.3 (3)°. The dihedral angle between the rings is 19.38 (10)°. The hydroxy group engages in an intramolecular O—H⋯O hydrogen bond with the carbonyl O atom of the propenone unit, generating an S(5) ring.

Related literature

For background to chalcones, see: Avila et al. (2008 ); Narender et al. (2007 ); Reddy et al. (2010 ).

Experimental

Crystal data

C₂₅H₃₀O₈
M_r = 458.49
Monoclinic, P c
a = 9.5990 (8) Å
b = 8.3294 (7) Å
c = 14.7444 (12) Å
β = 107.684 (1)°
V = 1123.17 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer
10316 measured reflections
2576 independent reflections
2433 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.082
S = 1.06
2576 reflections
302 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.90 (4)	1.65 (4)	2.480 (2)	153 (3)

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681103131X/hb6345sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103131X/hb6345Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681103131X/hb6345Isup3.cml

checkCIF report

Comment top

Chalcones or 1,3-diphenyl-2-propen-1-one derivatives flavonoids consist of two aromatic rings that are linked by a three-carbon α, β-unsaturated carbonyl unit (Avila et al., 2008; Reddy et al., 2010), and key precursors for the synthesis of a various flavonoids, some of which are components in food (Narender et al., 2007). We intend to use the intensely-orange title compound, (I), in the synthesis of other compounds. Its two benzene rings are connected through the –C(═ O)–CH═CH– unit, which is of an E configuration; the ring with the hydroxy substitutent is aligned at 19.5 (2) ° with this unit whereas the ring with the methoxymethyloxy substituents is aligned at 9.3 (3) °. The hydroxy group engages in intramolecular hydrogen bonding with the carbonyl O atom of the unit (Fig.1).

Related literature top

For background to chalcones, see: Avila et al. (2008); Narender et al. (2007); Reddy et al. (2010).

Experimental top

A solution of 2-hydroxy-4-methoxy-5,6-(2,2-dimethylchromane)acetophenone (100 mg, 0.45 mmol) and 3,4-bis(methoxymethyloxy)benzaldehyde (100 mg, 0.45 mmol) in ethanol (10 ml) was treated with 50% potassium hydroxide (1 ml). The mixture was stirred for 48 h. The mixture was poured into iced water (30 ml); this was acidified with 10% hydrochloric acid. The mixture was extracted with dichloromethane (3 x 20 ml). The organic layer was washed with water (3 x 10 ml) and brine (3 x 5 ml) followed by drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to yield a dark greenish syrup. The syrup was subjected to VLC for purification by using silica gel and eluting with a hexane:ethyl acetate solvent system (9:1) to give the title compound (520 mg, 30%) as orange prisms of (I), m.p. 363–368 K. The formulation was established by ¹H– and ¹³C-NMR spectroscopy.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2010).

Figures top

Fig. 1. The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(E)-3-[3,4-Bis(methoxymethoxy)phenyl]-1-(7-hydroxy-5-methoxy- 2,2-dimethylchroman-8-yl)prop-2-en-1-one top

Crystal data top

C₂₅H₃₀O₈	F(000) = 488
M_r = 458.49	D_x = 1.356 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 3857 reflections
a = 9.5990 (8) Å	θ = 2.2–28.2°
b = 8.3294 (7) Å	µ = 0.10 mm⁻¹
c = 14.7444 (12) Å	T = 100 K
β = 107.684 (1)°	Prism, orange
V = 1123.17 (16) Å³	0.30 × 0.25 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	2433 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −12→12
10316 measured reflections	k = −10→10
2576 independent reflections	l = −19→19

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0491P)² + 0.1273P] where P = (F_o² + 2F_c²)/3
2576 reflections	(Δ/σ)_max = 0.001
302 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₅H₃₀O₈	V = 1123.17 (16) Å³
M_r = 458.49	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 9.5990 (8) Å	µ = 0.10 mm⁻¹
b = 8.3294 (7) Å	T = 100 K
c = 14.7444 (12) Å	0.30 × 0.25 × 0.05 mm
β = 107.684 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	2433 reflections with I > 2σ(I)
10316 measured reflections	R_int = 0.037
2576 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
2576 reflections	Δρ_min = −0.20 e Å⁻³
302 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.50254 (17)	0.07085 (17)	0.49935 (10)	0.0174 (3)
O2	0.69328 (17)	0.04190 (19)	0.83437 (11)	0.0204 (3)
O3	0.79441 (18)	0.4985 (2)	0.67354 (12)	0.0221 (3)
H3	0.777 (4)	0.526 (4)	0.612 (3)	0.042 (9)*
O4	0.68542 (17)	0.51474 (19)	0.49826 (11)	0.0198 (3)
O5	0.01705 (16)	0.23344 (18)	0.10555 (10)	0.0178 (3)
O6	0.06369 (19)	0.0284 (2)	0.22016 (12)	0.0251 (4)
O7	0.05288 (16)	0.41671 (18)	−0.02881 (10)	0.0187 (3)
O8	0.05354 (17)	0.66810 (19)	−0.10124 (11)	0.0210 (3)
C1	0.4074 (2)	−0.0676 (2)	0.49859 (16)	0.0181 (4)
C2	0.3732 (3)	−0.1334 (3)	0.39786 (16)	0.0237 (5)
H2A	0.4635	−0.1720	0.3874	0.036*
H2B	0.3304	−0.0482	0.3520	0.036*
H2C	0.3036	−0.2224	0.3894	0.036*
C3	0.2692 (2)	−0.0069 (3)	0.51717 (18)	0.0228 (5)
H3A	0.2199	0.0701	0.4675	0.034*
H3B	0.2949	0.0460	0.5795	0.034*
H3C	0.2038	−0.0975	0.5165	0.034*
C4	0.4918 (2)	−0.1879 (3)	0.57238 (15)	0.0194 (4)
H4A	0.5793	−0.2241	0.5559	0.023*
H4B	0.4295	−0.2829	0.5718	0.023*
C5	0.5390 (2)	−0.1138 (3)	0.67197 (15)	0.0193 (4)
H5A	0.4542	−0.1096	0.6969	0.023*
H5B	0.6152	−0.1819	0.7153	0.023*
C6	0.5981 (2)	0.0529 (2)	0.66954 (15)	0.0160 (4)
C7	0.5763 (2)	0.1365 (3)	0.58478 (15)	0.0149 (4)
C8	0.6366 (2)	0.2927 (3)	0.58144 (15)	0.0148 (4)
C9	0.7257 (2)	0.3568 (3)	0.66940 (15)	0.0166 (4)
C10	0.7437 (2)	0.2780 (3)	0.75539 (15)	0.0174 (4)
H10	0.7988	0.3259	0.8137	0.021*
C11	0.6798 (2)	0.1281 (3)	0.75453 (15)	0.0161 (4)
C12	0.7820 (3)	0.1083 (3)	0.92334 (15)	0.0225 (5)
H12A	0.7826	0.0346	0.9753	0.034*
H12B	0.7416	0.2120	0.9342	0.034*
H12C	0.8822	0.1233	0.9211	0.034*
C13	0.6066 (2)	0.3942 (3)	0.49629 (14)	0.0150 (4)
C14	0.4826 (2)	0.3661 (3)	0.41004 (15)	0.0163 (4)
H14	0.4162	0.2807	0.4081	0.020*
C15	0.4642 (2)	0.4620 (3)	0.33424 (15)	0.0167 (4)
H15	0.5348	0.5446	0.3407	0.020*
C16	0.3495 (2)	0.4553 (3)	0.24339 (15)	0.0160 (4)
C17	0.3573 (2)	0.5633 (2)	0.17258 (15)	0.0178 (4)
H17	0.4318	0.6428	0.1869	0.021*
C18	0.2588 (2)	0.5565 (3)	0.08200 (15)	0.0174 (4)
H18	0.2660	0.6310	0.0349	0.021*
C19	0.1493 (2)	0.4408 (3)	0.05985 (14)	0.0163 (4)
C20	0.1330 (2)	0.3372 (2)	0.13222 (15)	0.0147 (4)
C21	0.2341 (2)	0.3429 (2)	0.22193 (15)	0.0159 (4)
H21	0.2257	0.2703	0.2697	0.019*
C22	−0.0247 (2)	0.1575 (3)	0.18001 (15)	0.0201 (4)
H22A	−0.0210	0.2375	0.2303	0.024*
H22B	−0.1270	0.1199	0.1543	0.024*
C23	0.0360 (3)	−0.1112 (3)	0.16131 (19)	0.0282 (5)
H23A	0.1017	−0.1979	0.1934	0.042*
H23B	0.0531	−0.0866	0.1006	0.042*
H23C	−0.0657	−0.1451	0.1496	0.042*
C24	0.0800 (2)	0.5048 (3)	−0.10506 (15)	0.0178 (4)
H24A	0.1831	0.4887	−0.1030	0.021*
H24B	0.0171	0.4616	−0.1664	0.021*
C25	−0.0952 (3)	0.7036 (3)	−0.10670 (18)	0.0271 (5)
H25A	−0.1074	0.8200	−0.1034	0.041*
H25B	−0.1188	0.6520	−0.0535	0.041*
H25C	−0.1607	0.6630	−0.1670	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0221 (8)	0.0131 (7)	0.0157 (7)	−0.0047 (6)	0.0039 (6)	−0.0013 (6)
O2	0.0239 (8)	0.0202 (8)	0.0156 (7)	−0.0001 (6)	0.0038 (6)	0.0013 (6)
O3	0.0244 (8)	0.0185 (8)	0.0178 (8)	−0.0070 (6)	−0.0018 (6)	0.0009 (6)
O4	0.0205 (8)	0.0183 (8)	0.0175 (7)	−0.0055 (6)	0.0013 (6)	0.0006 (6)
O5	0.0174 (7)	0.0182 (8)	0.0161 (7)	−0.0057 (6)	0.0026 (6)	0.0007 (6)
O6	0.0279 (9)	0.0205 (8)	0.0221 (8)	−0.0044 (7)	0.0004 (7)	0.0051 (6)
O7	0.0202 (8)	0.0189 (8)	0.0149 (7)	−0.0030 (6)	0.0023 (6)	0.0022 (6)
O8	0.0227 (8)	0.0182 (8)	0.0206 (8)	0.0002 (6)	0.0044 (7)	0.0026 (6)
C1	0.0199 (11)	0.0120 (10)	0.0202 (10)	−0.0048 (8)	0.0030 (8)	−0.0014 (8)
C2	0.0278 (12)	0.0180 (11)	0.0216 (11)	−0.0053 (9)	0.0019 (10)	−0.0033 (9)
C3	0.0165 (10)	0.0197 (10)	0.0313 (12)	0.0002 (8)	0.0061 (9)	0.0020 (9)
C4	0.0200 (11)	0.0128 (10)	0.0226 (11)	−0.0019 (8)	0.0024 (9)	0.0000 (8)
C5	0.0209 (11)	0.0150 (10)	0.0191 (11)	−0.0016 (8)	0.0020 (9)	0.0025 (8)
C6	0.0150 (10)	0.0137 (10)	0.0192 (10)	0.0007 (8)	0.0050 (8)	0.0002 (8)
C7	0.0116 (9)	0.0144 (10)	0.0179 (10)	0.0010 (7)	0.0032 (8)	−0.0017 (8)
C8	0.0133 (10)	0.0140 (10)	0.0165 (9)	0.0000 (8)	0.0035 (8)	−0.0017 (7)
C9	0.0146 (10)	0.0151 (10)	0.0194 (11)	0.0007 (8)	0.0039 (8)	−0.0004 (8)
C10	0.0149 (10)	0.0189 (10)	0.0161 (10)	0.0004 (8)	0.0010 (8)	−0.0016 (8)
C11	0.0134 (10)	0.0181 (10)	0.0167 (10)	0.0031 (8)	0.0044 (8)	0.0030 (8)
C12	0.0289 (12)	0.0225 (11)	0.0134 (10)	0.0044 (10)	0.0022 (9)	0.0010 (9)
C13	0.0143 (10)	0.0139 (10)	0.0167 (10)	0.0004 (8)	0.0046 (8)	−0.0009 (7)
C14	0.0162 (10)	0.0134 (10)	0.0179 (10)	−0.0016 (8)	0.0030 (8)	−0.0014 (8)
C15	0.0178 (10)	0.0138 (10)	0.0188 (10)	−0.0012 (8)	0.0058 (8)	−0.0023 (8)
C16	0.0167 (10)	0.0150 (10)	0.0169 (10)	−0.0001 (8)	0.0058 (8)	−0.0005 (8)
C17	0.0203 (11)	0.0139 (10)	0.0189 (10)	−0.0024 (8)	0.0055 (8)	−0.0005 (8)
C18	0.0190 (10)	0.0162 (11)	0.0172 (10)	−0.0007 (8)	0.0059 (8)	0.0018 (8)
C19	0.0189 (10)	0.0152 (10)	0.0140 (10)	0.0018 (8)	0.0037 (8)	−0.0006 (8)
C20	0.0156 (10)	0.0106 (9)	0.0189 (10)	−0.0005 (8)	0.0065 (8)	−0.0020 (8)
C21	0.0166 (10)	0.0143 (10)	0.0170 (10)	0.0006 (8)	0.0054 (8)	0.0016 (8)
C22	0.0206 (11)	0.0229 (11)	0.0169 (10)	−0.0047 (9)	0.0057 (9)	−0.0004 (8)
C23	0.0282 (13)	0.0222 (12)	0.0345 (14)	−0.0057 (10)	0.0099 (11)	−0.0002 (10)
C24	0.0186 (10)	0.0193 (11)	0.0149 (10)	0.0002 (8)	0.0043 (8)	0.0020 (8)
C25	0.0267 (13)	0.0280 (12)	0.0260 (12)	0.0072 (10)	0.0070 (10)	0.0006 (10)

Geometric parameters (Å, º) top

O1—C7	1.358 (3)	C8—C9	1.423 (3)
O1—C1	1.469 (2)	C8—C13	1.467 (3)
O2—C11	1.351 (3)	C9—C10	1.391 (3)
O2—C12	1.440 (3)	C10—C11	1.390 (3)
O3—C9	1.344 (3)	C10—H10	0.9500
O3—H3	0.90 (4)	C12—H12A	0.9800
O4—C13	1.253 (3)	C12—H12B	0.9800
O5—C20	1.369 (2)	C12—H12C	0.9800
O5—C22	1.426 (2)	C13—C14	1.472 (3)
O6—C22	1.387 (3)	C14—C15	1.341 (3)
O6—C23	1.427 (3)	C14—H14	0.9500
O7—C19	1.368 (3)	C15—C16	1.454 (3)
O7—C24	1.431 (2)	C15—H15	0.9500
O8—C24	1.388 (3)	C16—C17	1.397 (3)
O8—C25	1.436 (3)	C16—C21	1.410 (3)
C1—C4	1.519 (3)	C17—C18	1.384 (3)
C1—C3	1.520 (3)	C17—H17	0.9500
C1—C2	1.523 (3)	C18—C19	1.389 (3)
C2—H2A	0.9800	C18—H18	0.9500
C2—H2B	0.9800	C19—C20	1.418 (3)
C2—H2C	0.9800	C20—C21	1.383 (3)
C3—H3A	0.9800	C21—H21	0.9500
C3—H3B	0.9800	C22—H22A	0.9900
C3—H3C	0.9800	C22—H22B	0.9900
C4—C5	1.529 (3)	C23—H23A	0.9800
C4—H4A	0.9900	C23—H23B	0.9800
C4—H4B	0.9900	C23—H23C	0.9800
C5—C6	1.504 (3)	C24—H24A	0.9900
C5—H5A	0.9900	C24—H24B	0.9900
C5—H5B	0.9900	C25—H25A	0.9800
C6—C7	1.390 (3)	C25—H25B	0.9800
C6—C11	1.407 (3)	C25—H25C	0.9800
C7—C8	1.431 (3)

C7—O1—C1	118.07 (16)	O2—C12—H12B	109.5
C11—O2—C12	117.60 (17)	H12A—C12—H12B	109.5
C9—O3—H3	104 (2)	O2—C12—H12C	109.5
C20—O5—C22	116.93 (16)	H12A—C12—H12C	109.5
C22—O6—C23	113.33 (18)	H12B—C12—H12C	109.5
C19—O7—C24	116.34 (16)	O4—C13—C8	118.78 (18)
C24—O8—C25	113.00 (18)	O4—C13—C14	118.10 (18)
O1—C1—C4	108.51 (17)	C8—C13—C14	123.03 (18)
O1—C1—C3	108.19 (17)	C15—C14—C13	119.54 (19)
C4—C1—C3	113.25 (18)	C15—C14—H14	120.2
O1—C1—C2	103.86 (16)	C13—C14—H14	120.2
C4—C1—C2	111.78 (18)	C14—C15—C16	128.0 (2)
C3—C1—C2	110.74 (19)	C14—C15—H15	116.0
C1—C2—H2A	109.5	C16—C15—H15	116.0
C1—C2—H2B	109.5	C17—C16—C21	118.45 (19)
H2A—C2—H2B	109.5	C17—C16—C15	117.75 (19)
C1—C2—H2C	109.5	C21—C16—C15	123.77 (18)
H2A—C2—H2C	109.5	C18—C17—C16	121.24 (19)
H2B—C2—H2C	109.5	C18—C17—H17	119.4
C1—C3—H3A	109.5	C16—C17—H17	119.4
C1—C3—H3B	109.5	C17—C18—C19	120.12 (19)
H3A—C3—H3B	109.5	C17—C18—H18	119.9
C1—C3—H3C	109.5	C19—C18—H18	119.9
H3A—C3—H3C	109.5	O7—C19—C18	124.78 (18)
H3B—C3—H3C	109.5	O7—C19—C20	115.63 (18)
C1—C4—C5	111.09 (18)	C18—C19—C20	119.59 (19)
C1—C4—H4A	109.4	O5—C20—C21	124.72 (18)
C5—C4—H4A	109.4	O5—C20—C19	115.73 (18)
C1—C4—H4B	109.4	C21—C20—C19	119.53 (18)
C5—C4—H4B	109.4	C20—C21—C16	120.83 (18)
H4A—C4—H4B	108.0	C20—C21—H21	119.6
C6—C5—C4	110.70 (17)	C16—C21—H21	119.6
C6—C5—H5A	109.5	O6—C22—O5	113.22 (18)
C4—C5—H5A	109.5	O6—C22—H22A	108.9
C6—C5—H5B	109.5	O5—C22—H22A	108.9
C4—C5—H5B	109.5	O6—C22—H22B	108.9
H5A—C5—H5B	108.1	O5—C22—H22B	108.9
C7—C6—C11	117.93 (19)	H22A—C22—H22B	107.7
C7—C6—C5	121.93 (19)	O6—C23—H23A	109.5
C11—C6—C5	120.13 (18)	O6—C23—H23B	109.5
O1—C7—C6	121.74 (18)	H23A—C23—H23B	109.5
O1—C7—C8	115.87 (17)	O6—C23—H23C	109.5
C6—C7—C8	122.31 (19)	H23A—C23—H23C	109.5
C9—C8—C7	116.57 (18)	H23B—C23—H23C	109.5
C9—C8—C13	118.11 (18)	O8—C24—O7	113.05 (17)
C7—C8—C13	125.21 (18)	O8—C24—H24A	109.0
O3—C9—C10	116.71 (19)	O7—C24—H24A	109.0
O3—C9—C8	121.45 (19)	O8—C24—H24B	109.0
C10—C9—C8	121.84 (19)	O7—C24—H24B	109.0
C9—C10—C11	118.90 (19)	H24A—C24—H24B	107.8
C9—C10—H10	120.5	O8—C25—H25A	109.5
C11—C10—H10	120.5	O8—C25—H25B	109.5
O2—C11—C10	122.98 (19)	H25A—C25—H25B	109.5
O2—C11—C6	114.77 (18)	O8—C25—H25C	109.5
C10—C11—C6	122.24 (19)	H25A—C25—H25C	109.5
O2—C12—H12A	109.5	H25B—C25—H25C	109.5

C7—O1—C1—C4	−47.8 (2)	C5—C6—C11—C10	176.19 (19)
C7—O1—C1—C3	75.5 (2)	C9—C8—C13—O4	16.7 (3)
C7—O1—C1—C2	−166.83 (18)	C7—C8—C13—O4	−167.3 (2)
O1—C1—C4—C5	60.1 (2)	C9—C8—C13—C14	−159.84 (19)
C3—C1—C4—C5	−60.0 (2)	C7—C8—C13—C14	16.2 (3)
C2—C1—C4—C5	174.09 (18)	O4—C13—C14—C15	4.9 (3)
C1—C4—C5—C6	−43.8 (2)	C8—C13—C14—C15	−178.5 (2)
C4—C5—C6—C7	14.6 (3)	C13—C14—C15—C16	−179.6 (2)
C4—C5—C6—C11	−164.52 (19)	C14—C15—C16—C17	−176.5 (2)
C1—O1—C7—C6	18.7 (3)	C14—C15—C16—C21	1.3 (3)
C1—O1—C7—C8	−164.55 (17)	C21—C16—C17—C18	−2.9 (3)
C11—C6—C7—O1	177.99 (18)	C15—C16—C17—C18	175.06 (19)
C5—C6—C7—O1	−1.2 (3)	C16—C17—C18—C19	0.0 (3)
C11—C6—C7—C8	1.5 (3)	C24—O7—C19—C18	7.9 (3)
C5—C6—C7—C8	−177.66 (19)	C24—O7—C19—C20	−171.75 (17)
O1—C7—C8—C9	−174.29 (17)	C17—C18—C19—O7	−175.3 (2)
C6—C7—C8—C9	2.4 (3)	C17—C18—C19—C20	4.3 (3)
O1—C7—C8—C13	9.6 (3)	C22—O5—C20—C21	17.4 (3)
C6—C7—C8—C13	−173.71 (19)	C22—O5—C20—C19	−164.53 (18)
C7—C8—C9—O3	176.20 (19)	O7—C19—C20—O5	−4.1 (3)
C13—C8—C9—O3	−7.4 (3)	C18—C19—C20—O5	176.19 (18)
C7—C8—C9—C10	−5.1 (3)	O7—C19—C20—C21	174.01 (18)
C13—C8—C9—C10	171.26 (19)	C18—C19—C20—C21	−5.7 (3)
O3—C9—C10—C11	−177.43 (19)	O5—C20—C21—C16	−179.29 (19)
C8—C9—C10—C11	3.8 (3)	C19—C20—C21—C16	2.7 (3)
C12—O2—C11—C10	−1.9 (3)	C17—C16—C21—C20	1.5 (3)
C12—O2—C11—C6	176.82 (18)	C15—C16—C21—C20	−176.33 (19)
C9—C10—C11—O2	179.01 (19)	C23—O6—C22—O5	−75.0 (2)
C9—C10—C11—C6	0.4 (3)	C20—O5—C22—O6	−79.4 (2)
C7—C6—C11—O2	178.28 (17)	C25—O8—C24—O7	−60.4 (2)
C5—C6—C11—O2	−2.6 (3)	C19—O7—C24—O8	−70.3 (2)
C7—C6—C11—C10	−3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.90 (4)	1.65 (4)	2.480 (2)	153 (3)

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀O₈
M_r	458.49
Crystal system, space group	Monoclinic, Pc
Temperature (K)	100
a, b, c (Å)	9.5990 (8), 8.3294 (7), 14.7444 (12)
β (°)	107.684 (1)
V (Å³)	1123.17 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10316, 2576, 2433
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.082, 1.06
No. of reflections	2576
No. of parameters	302
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.90 (4)	1.65 (4)	2.480 (2)	153 (3)

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Avila, H. P., Smania, E. F. A., Monache, F. D. & Junior, A. S. (2008). Bioorg. Med. Chem. 16, 9790–9794. CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Narender, T., Reddy, K.P., Shweta, Srivastava, K., Mishra, D.K., & Puri, S. K. (2007). Org. Lett. 9, 5369–5372. CrossRef CAS Google Scholar
Reddy, N. P., Aparoy, P., Reddy, T. C. M., Achari, C., Sridhar, P. R. & Reddanna, P. (2010). Bioorg. Med. Chem. 18, 5807–5815. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2300

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

(E)-3-[3,4-Bis(meth­­oxy­meth­oxy)phen­yl]-1-(7-hy­dr­oxy-5-meth­­oxy-2,2-di­methyl­chroman-8-yl)prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-3-[3,4-Bis(methoxymethoxy)phenyl]-1-(7-hydroxy-5-methoxy-2,2-dimethylchroman-8-yl)prop-2-en-1-one