E-[4-(β-d-Allopyranos­yloxy)phen­yl]-1-(4-chloro­phen­yl)prop-2-enone ethanol solvate

Yang, C.; Luo, H.; Yin, X.; Li, Y.; Yin, S.

doi:10.1107/S1600536809006424

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o634

doi:10.1107/S1600536809006424

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E-[4-(β-D-Allopyranosyloxy)phenyl]-1-(4-chlorophenyl)prop-2-enone ethanol solvate

Cong-ling Yang,^a Hua-ling Luo,^a Xiu-juan Yin,^a ^* Ying Li ^a and Shu-fan Yin ^a

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: chuandayouji217@163.com

(Received 10 January 2009; accepted 21 February 2009; online 28 February 2009)

The title compound, C₂₁H₂₁ClO₇·C₂H₅OH was synthesized by the condensation reaction between helicid [systematic name: 4-(β-D-allopyranosyloxy)benzaldehyde] and 4-chloroacetophenone in ethanol. In the molecular structure, the pyranoside ring adopts a chair conformation. In the crystal structure, the molecules are linked by intermolecular O—H⋯O hydrogen bonds involving the OH groups from the pyranoside unit and from the ethanol solvent molecule.

Related literature

For helicid, see: Chen et al. (1981 ) and for its biological activity, see: Sha & Mao (1987 ). For the pharmacological activity of some helicid derivatives, see: Fan et al. (2007 ).

Experimental

Crystal data

C₂₁H₂₁ClO₇·C₂H₆O
M_r = 466.90
Monoclinic, P 2₁
a = 11.000 (5) Å
b = 7.712 (3) Å
c = 13.213 (4) Å
β = 92.08 (2)°
V = 1120.2 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 292 K
0.48 × 0.44 × 0.36 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: for a sphere [WinGX; Farrugia, 1999 )] T_min = 0.903, T_max = 0.926
2921 measured reflections
2815 independent reflections
2305 reflections with I > 2σ(I)
R_int = 0.008
3 standard reflections every 200 reflections intensity decay: 1.4%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.143
S = 1.10
2815 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 562 Friedel pairs
Flack parameter: 0.14 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3ⁱ	0.82	2.02	2.809 (4)	160
O4—H4O⋯O2ⁱⁱ	0.82	1.88	2.694 (4)	171
O5—H5O⋯O8ⁱⁱ	0.82	1.97	2.696 (5)	148
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) x, y+1, z.

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006424/bh2216sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006424/bh2216Isup2.hkl

checkCIF report

Comment top

The natural compound helicid, 4-(β-D-allopyranosyloxy)benzaldehyde, which is extracted from the fruit of Helicia nilagirica Beed (Chen et al., 1981) is a major active ingredient of Chinese herbal medicine. It has good biological effects on the central nervous system with a low toxicity (Sha & Mao, 1987). Some helicid derivatives have been reported with good pharmacological activities (Fan et al., 2007). The title compound, a new helicid derivative, was synthesized via reaction of helicid and 4-chloroacetophenone, in good yield.

In the molecule of the title compound (Fig. 1), the average of C—C bond lengths in the six-membered pyranoside ring is 1.522 (5) Å. The average C(sp³)—O and C(sp²)—O bond lengths are 1.414 (5) and 1.392 (4) Å, respectively. The pyranoside ring adopts a chair conformation with hydroxyl group at C3 in axial position and the other substituents at C1, C2 and C4, in equatorial positions.

In the crystal packing, the molecules are connected by intermolecular O—H···.O hydrogen bonds (Table 1) involving O1 and O7 atoms and the hydroxyl groups in the main molecule and in the ethanol solvent molecule, forming a three-dimensional network.

Related literature top

For helicid, see: Chen et al. (1981) and for its biological activity, see: Sha & Mao (1987). For the pharmacological activity of some helicid derivatives, see: Fan et al. (2007).

Experimental top

To a solution of helicid (1.420 g, 5 mmol) in ethanol (20 ml), 10% aqueous solution of sodium hydroxide was added until helicid was dissolved completely. Then 4-chloroacetophenone (0.847 g, 5.5 mmol) was added dropwise, with the vessel placed in an ice bath. The reaction was monitored by TLC. After the reaction completed, the mixture was cooled to room temperature, and then neutralized with diluted hydrochloric acid. The solution was extracted three times with ethyl acetate, and the combined organic layers were dried with anhydrous Na₂SO₄, filtered, and evaporated in vacuo to get the crude product. The title compound was recrystallized twice from ethanol, and colourless single crystals were finally obtained by slow evaporation of an ethanol solution, at room temperature.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.

E-[4-(β-D-Allopyranosyloxy)phenyl]-1-(4-chlorophenyl)prop-2-enone ethanol solvate top

Crystal data top

C₂₁H₂₁ClO₇·C₂H₆O	F(000) = 492
M_r = 466.90	D_x = 1.384 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 19 reflections
a = 11.000 (5) Å	θ = 4.5–7.4°
b = 7.712 (3) Å	µ = 0.22 mm⁻¹
c = 13.213 (4) Å	T = 292 K
β = 92.08 (2)°	Block, colourless
V = 1120.2 (8) Å³	0.48 × 0.44 × 0.36 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	2305 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.008
Graphite monochromator	θ_max = 25.5°, θ_min = 1.5°
ω/–2θ scans	h = −13→13
Absorption correction: for a sphere [WinGX; Farrugia, 1999)]	k = −9→9
T_min = 0.903, T_max = 0.926	l = −15→15
2921 measured reflections	3 standard reflections every 200 reflections
2815 independent reflections	intensity decay: 1.4%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.099P)² + 0.0279P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.143	(Δ/σ)_max = 0.001
S = 1.10	Δρ_max = 0.43 e Å⁻³
2815 reflections	Δρ_min = −0.30 e Å⁻³
281 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.056 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 562 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.14 (12)

Crystal data top

C₂₁H₂₁ClO₇·C₂H₆O	V = 1120.2 (8) Å³
M_r = 466.90	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.000 (5) Å	µ = 0.22 mm⁻¹
b = 7.712 (3) Å	T = 292 K
c = 13.213 (4) Å	0.48 × 0.44 × 0.36 mm
β = 92.08 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2305 reflections with I > 2σ(I)
Absorption correction: for a sphere [WinGX; Farrugia, 1999)]	R_int = 0.008
T_min = 0.903, T_max = 0.926	3 standard reflections every 200 reflections
2921 measured reflections	intensity decay: 1.4%
2815 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.143	Δρ_max = 0.43 e Å⁻³
S = 1.10	Δρ_min = −0.30 e Å⁻³
2815 reflections	Absolute structure: Flack (1983), 562 Friedel pairs
281 parameters	Absolute structure parameter: 0.14 (12)
1 restraint

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

	x	y	z	U_iso*/U_eq
Cl1	1.19712 (12)	0.6652 (2)	1.29357 (8)	0.0730 (4)
O1	0.6580 (2)	0.7216 (3)	0.27293 (17)	0.0385 (6)
O2	0.5789 (3)	0.4472 (3)	0.1477 (2)	0.0478 (7)
H2O	0.5624	0.4470	0.0867	0.072*
O3	0.4614 (2)	0.8598 (4)	0.05711 (19)	0.0469 (7)
H3O	0.4201	0.9331	0.0848	0.070*
O4	0.5518 (3)	1.1087 (3)	0.1920 (2)	0.0452 (7)
H4O	0.5665	1.2117	0.1830	0.068*
O5	0.8179 (2)	1.1280 (4)	0.2200 (2)	0.0481 (7)
H5O	0.7732	1.2009	0.2443	0.072*
O6	0.8220 (2)	0.8419 (4)	0.35453 (16)	0.0423 (6)
O7	0.7388 (3)	0.5708 (5)	0.9598 (2)	0.0564 (8)
C1	0.5463 (3)	0.7382 (5)	0.2130 (2)	0.0353 (8)
H1	0.4880	0.8055	0.2513	0.042*
C2	0.5718 (4)	0.8348 (5)	0.1143 (3)	0.0376 (8)
H2	0.6262	0.7634	0.0745	0.045*
C3	0.6344 (3)	1.0062 (5)	0.1375 (3)	0.0386 (8)
H3	0.6536	1.0646	0.0742	0.046*
C4	0.7517 (3)	0.9739 (5)	0.2010 (3)	0.0373 (8)
H4	0.8030	0.8947	0.1633	0.045*
C5	0.7157 (3)	0.8832 (5)	0.2974 (3)	0.0379 (8)
H5	0.6621	0.9570	0.3365	0.046*
C6	0.4973 (4)	0.5577 (5)	0.1971 (3)	0.0431 (9)
H6A	0.4793	0.5079	0.2623	0.052*
H6B	0.4217	0.5640	0.1571	0.052*
C7	0.8102 (3)	0.7956 (5)	0.4555 (3)	0.0401 (9)
C8	0.6991 (3)	0.7808 (6)	0.4999 (3)	0.0468 (10)
H8	0.6269	0.8012	0.4631	0.056*
C9	0.6987 (3)	0.7340 (6)	0.6024 (3)	0.0475 (9)
H9	0.6247	0.7247	0.6338	0.057*
C10	0.8041 (3)	0.7015 (5)	0.6579 (3)	0.0423 (9)
C11	0.9136 (4)	0.7145 (6)	0.6094 (3)	0.0497 (10)
H11	0.9861	0.6905	0.6450	0.060*
C12	0.9159 (4)	0.7624 (6)	0.5098 (3)	0.0490 (10)
H12	0.9901	0.7725	0.4787	0.059*
C13	0.7923 (3)	0.6580 (6)	0.7646 (3)	0.0469 (9)
H13	0.7131	0.6442	0.7855	0.056*
C14	0.8794 (3)	0.6351 (6)	0.8365 (3)	0.0454 (9)
H14	0.9610	0.6407	0.8206	0.054*
C15	0.8446 (3)	0.6010 (5)	0.9412 (3)	0.0409 (9)
C16	0.9379 (3)	0.6058 (5)	1.0255 (3)	0.0379 (8)
C17	0.9023 (4)	0.5637 (5)	1.1225 (3)	0.0444 (9)
H17	0.8234	0.5253	1.1321	0.053*
C18	0.9827 (4)	0.5781 (6)	1.2042 (3)	0.0480 (10)
H18	0.9586	0.5490	1.2688	0.058*
C19	1.0986 (4)	0.6360 (5)	1.1897 (3)	0.0453 (9)
C20	1.1381 (4)	0.6725 (6)	1.0948 (3)	0.0489 (10)
H20	1.2180	0.7066	1.0859	0.059*
C21	1.0571 (3)	0.6578 (5)	1.0122 (3)	0.0420 (9)
H21	1.0829	0.6830	0.9475	0.050*
O8	0.7509 (3)	0.3817 (5)	0.3469 (3)	0.0700 (10)*
H8A	0.6815	0.3984	0.3242	0.105*
C22	0.7467 (4)	0.3290 (7)	0.4506 (3)	0.0590 (11)*
H22A	0.7872	0.4154	0.4931	0.071*
H22B	0.7903	0.2204	0.4596	0.071*
C23	0.6220 (6)	0.3068 (9)	0.4826 (5)	0.0845 (16)*
H23A	0.5798	0.2276	0.4377	0.127*
H23B	0.5812	0.4168	0.4810	0.127*
H23C	0.6231	0.2614	0.5503	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0730 (8)	0.1004 (10)	0.0442 (6)	0.0021 (8)	−0.0177 (5)	−0.0029 (6)
O1	0.0469 (14)	0.0345 (11)	0.0336 (12)	0.0010 (12)	−0.0078 (11)	0.0031 (11)
O2	0.0706 (19)	0.0373 (14)	0.0350 (14)	0.0064 (14)	−0.0040 (14)	−0.0004 (11)
O3	0.0485 (16)	0.0526 (16)	0.0388 (14)	0.0065 (14)	−0.0115 (12)	0.0005 (13)
O4	0.0499 (16)	0.0336 (13)	0.0525 (16)	0.0062 (12)	0.0054 (12)	0.0011 (12)
O5	0.0461 (15)	0.0473 (15)	0.0513 (16)	−0.0075 (13)	0.0087 (12)	−0.0051 (13)
O6	0.0363 (13)	0.0620 (16)	0.0284 (12)	0.0025 (13)	−0.0022 (10)	0.0014 (12)
O7	0.0444 (16)	0.084 (2)	0.0410 (14)	−0.0089 (16)	0.0028 (12)	0.0011 (15)
C1	0.0376 (19)	0.0380 (17)	0.0299 (17)	0.0017 (15)	−0.0021 (15)	0.0000 (15)
C2	0.045 (2)	0.0357 (17)	0.0313 (17)	0.0040 (17)	−0.0020 (16)	0.0036 (16)
C3	0.048 (2)	0.0377 (18)	0.0303 (17)	0.0028 (17)	0.0023 (15)	0.0054 (15)
C4	0.042 (2)	0.0375 (18)	0.0325 (18)	0.0025 (16)	0.0023 (15)	−0.0031 (15)
C5	0.038 (2)	0.0394 (19)	0.0358 (19)	−0.0007 (16)	−0.0045 (16)	−0.0031 (15)
C6	0.047 (2)	0.0405 (19)	0.042 (2)	−0.0029 (18)	−0.0032 (17)	0.0031 (16)
C7	0.0409 (19)	0.047 (2)	0.0323 (18)	0.0004 (18)	−0.0026 (15)	−0.0035 (15)
C8	0.0351 (19)	0.070 (3)	0.0353 (18)	0.005 (2)	−0.0038 (15)	0.0006 (18)
C9	0.0367 (19)	0.070 (3)	0.0360 (19)	0.0027 (19)	0.0038 (16)	0.001 (2)
C10	0.042 (2)	0.054 (2)	0.0309 (17)	0.0017 (19)	−0.0012 (15)	0.0003 (17)
C11	0.040 (2)	0.072 (3)	0.0367 (19)	0.003 (2)	−0.0089 (16)	0.004 (2)
C12	0.040 (2)	0.070 (3)	0.0373 (19)	−0.001 (2)	0.0023 (16)	−0.0004 (19)
C13	0.045 (2)	0.061 (2)	0.0337 (18)	0.001 (2)	−0.0011 (16)	0.0002 (19)
C14	0.042 (2)	0.061 (2)	0.0332 (18)	−0.004 (2)	0.0007 (16)	0.0007 (18)
C15	0.042 (2)	0.046 (2)	0.0349 (18)	−0.0024 (17)	0.0034 (16)	−0.0016 (16)
C16	0.046 (2)	0.0378 (18)	0.0298 (17)	−0.0009 (17)	0.0019 (15)	0.0024 (15)
C17	0.043 (2)	0.051 (2)	0.040 (2)	0.0053 (18)	0.0057 (16)	0.0038 (17)
C18	0.058 (2)	0.056 (2)	0.0296 (18)	0.009 (2)	0.0033 (17)	0.0043 (17)
C19	0.055 (2)	0.047 (2)	0.0336 (18)	0.003 (2)	−0.0049 (16)	0.0001 (17)
C20	0.045 (2)	0.056 (3)	0.045 (2)	−0.006 (2)	0.0004 (17)	0.003 (2)
C21	0.046 (2)	0.048 (2)	0.0321 (17)	−0.0023 (19)	0.0013 (15)	0.0031 (17)

Geometric parameters (Å, º) top

Cl1—C19	1.732 (4)	C9—C10	1.372 (5)
O1—C5	1.431 (4)	C9—H9	0.9300
O1—C1	1.443 (4)	C10—C11	1.389 (5)
O2—C6	1.414 (5)	C10—C13	1.460 (5)
O2—H2O	0.8200	C11—C12	1.368 (6)
O3—C2	1.420 (4)	C11—H11	0.9300
O3—H3O	0.8200	C12—H12	0.9300
O4—C3	1.420 (5)	C13—C14	1.336 (5)
O4—H4O	0.8200	C13—H13	0.9300
O5—C4	1.412 (5)	C14—C15	1.473 (5)
O5—H5O	0.8200	C14—H14	0.9300
O6—C7	1.392 (4)	C15—C16	1.488 (5)
O6—C5	1.404 (4)	C16—C21	1.389 (5)
O7—C15	1.221 (5)	C16—C17	1.392 (5)
C1—C6	1.505 (5)	C17—C18	1.376 (5)
C1—C2	1.537 (5)	C17—H17	0.9300
C1—H1	0.9800	C18—C19	1.371 (6)
C2—C3	1.516 (5)	C18—H18	0.9300
C2—H2	0.9800	C19—C20	1.371 (6)
C3—C4	1.533 (5)	C20—C21	1.388 (5)
C3—H3	0.9800	C20—H20	0.9300
C4—C5	1.519 (5)	C21—H21	0.9300
C4—H4	0.9800	O8—C22	1.431 (5)
C5—H5	0.9800	O8—H8A	0.8200
C6—H6A	0.9700	C22—C23	1.460 (7)
C6—H6B	0.9700	C22—H22A	0.9700
C7—C12	1.368 (5)	C22—H22B	0.9700
C7—C8	1.379 (5)	C23—H23A	0.9600
C8—C9	1.402 (5)	C23—H23B	0.9600
C8—H8	0.9300	C23—H23C	0.9600

C5—O1—C1	114.1 (3)	C8—C9—H9	119.0
C6—O2—H2O	109.5	C9—C10—C11	118.1 (3)
C2—O3—H3O	109.5	C9—C10—C13	117.1 (3)
C3—O4—H4O	109.5	C11—C10—C13	124.8 (3)
C4—O5—H5O	109.5	C12—C11—C10	120.7 (3)
C7—O6—C5	117.9 (3)	C12—C11—H11	119.7
O1—C1—C6	106.7 (3)	C10—C11—H11	119.7
O1—C1—C2	109.3 (3)	C11—C12—C7	120.7 (4)
C6—C1—C2	113.9 (3)	C11—C12—H12	119.7
O1—C1—H1	108.9	C7—C12—H12	119.7
C6—C1—H1	108.9	C14—C13—C10	129.1 (4)
C2—C1—H1	108.9	C14—C13—H13	115.5
O3—C2—C3	111.2 (3)	C10—C13—H13	115.5
O3—C2—C1	109.8 (3)	C13—C14—C15	119.1 (3)
C3—C2—C1	110.3 (3)	C13—C14—H14	120.4
O3—C2—H2	108.5	C15—C14—H14	120.4
C3—C2—H2	108.5	O7—C15—C14	120.4 (3)
C1—C2—H2	108.5	O7—C15—C16	119.4 (3)
O4—C3—C2	107.1 (3)	C14—C15—C16	120.2 (3)
O4—C3—C4	110.7 (3)	C21—C16—C17	118.9 (3)
C2—C3—C4	109.6 (3)	C21—C16—C15	122.8 (3)
O4—C3—H3	109.8	C17—C16—C15	118.3 (3)
C2—C3—H3	109.8	C18—C17—C16	120.7 (4)
C4—C3—H3	109.8	C18—C17—H17	119.7
O5—C4—C5	112.7 (3)	C16—C17—H17	119.7
O5—C4—C3	112.3 (3)	C19—C18—C17	119.4 (4)
C5—C4—C3	107.1 (3)	C19—C18—H18	120.3
O5—C4—H4	108.2	C17—C18—H18	120.3
C5—C4—H4	108.2	C18—C19—C20	121.5 (4)
C3—C4—H4	108.2	C18—C19—Cl1	119.3 (3)
O6—C5—O1	106.1 (3)	C20—C19—Cl1	119.2 (3)
O6—C5—C4	108.6 (3)	C19—C20—C21	119.2 (4)
O1—C5—C4	109.8 (3)	C19—C20—H20	120.4
O6—C5—H5	110.8	C21—C20—H20	120.4
O1—C5—H5	110.8	C20—C21—C16	120.3 (4)
C4—C5—H5	110.8	C20—C21—H21	119.8
O2—C6—C1	113.1 (3)	C16—C21—H21	119.8
O2—C6—H6A	109.0	C22—O8—H8A	109.5
C1—C6—H6A	109.0	O8—C22—C23	112.0 (4)
O2—C6—H6B	109.0	O8—C22—H22A	109.2
C1—C6—H6B	109.0	C23—C22—H22A	109.2
H6A—C6—H6B	107.8	O8—C22—H22B	109.2
C12—C7—C8	120.7 (3)	C23—C22—H22B	109.2
C12—C7—O6	116.4 (3)	H22A—C22—H22B	107.9
C8—C7—O6	122.9 (3)	C22—C23—H23A	109.5
C7—C8—C9	117.8 (3)	C22—C23—H23B	109.5
C7—C8—H8	121.1	H23A—C23—H23B	109.5
C9—C8—H8	121.1	C22—C23—H23C	109.5
C10—C9—C8	122.0 (4)	H23A—C23—H23C	109.5
C10—C9—H9	119.0	H23B—C23—H23C	109.5

C5—O1—C1—C6	−178.6 (3)	C7—C8—C9—C10	−0.7 (7)
C5—O1—C1—C2	57.8 (4)	C8—C9—C10—C11	−0.6 (7)
O1—C1—C2—O3	−177.0 (3)	C8—C9—C10—C13	178.6 (4)
C6—C1—C2—O3	63.7 (4)	C9—C10—C11—C12	1.5 (7)
O1—C1—C2—C3	−54.1 (4)	C13—C10—C11—C12	−177.6 (4)
C6—C1—C2—C3	−173.4 (3)	C10—C11—C12—C7	−1.1 (7)
O3—C2—C3—O4	58.7 (4)	C8—C7—C12—C11	−0.2 (7)
C1—C2—C3—O4	−63.3 (4)	O6—C7—C12—C11	−179.5 (4)
O3—C2—C3—C4	178.9 (3)	C9—C10—C13—C14	−173.8 (4)
C1—C2—C3—C4	56.8 (4)	C11—C10—C13—C14	5.2 (7)
O4—C3—C4—O5	−65.5 (4)	C10—C13—C14—C15	176.6 (4)
C2—C3—C4—O5	176.5 (3)	C13—C14—C15—O7	9.8 (6)
O4—C3—C4—C5	58.7 (4)	C13—C14—C15—C16	−169.3 (4)
C2—C3—C4—C5	−59.2 (4)	O7—C15—C16—C21	−172.7 (4)
C7—O6—C5—O1	−76.9 (4)	C14—C15—C16—C21	6.4 (6)
C7—O6—C5—C4	165.2 (3)	O7—C15—C16—C17	4.3 (5)
C1—O1—C5—O6	−179.6 (3)	C14—C15—C16—C17	−176.6 (4)
C1—O1—C5—C4	−62.5 (4)	C21—C16—C17—C18	1.9 (6)
O5—C4—C5—O6	−59.6 (4)	C15—C16—C17—C18	−175.2 (3)
C3—C4—C5—O6	176.3 (3)	C16—C17—C18—C19	0.5 (6)
O5—C4—C5—O1	−175.2 (3)	C17—C18—C19—C20	−2.9 (6)
C3—C4—C5—O1	60.8 (3)	C17—C18—C19—Cl1	176.6 (3)
O1—C1—C6—O2	−58.8 (4)	C18—C19—C20—C21	2.9 (6)
C2—C1—C6—O2	61.8 (4)	Cl1—C19—C20—C21	−176.6 (3)
C5—O6—C7—C12	−177.7 (3)	C19—C20—C21—C16	−0.4 (6)
C5—O6—C7—C8	3.1 (6)	C17—C16—C21—C20	−2.0 (6)
C12—C7—C8—C9	1.1 (6)	C15—C16—C21—C20	175.1 (4)
O6—C7—C8—C9	−179.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3ⁱ	0.82	2.02	2.809 (4)	160
O4—H4O···O2ⁱⁱ	0.82	1.88	2.694 (4)	171
O5—H5O···O8ⁱⁱ	0.82	1.97	2.696 (5)	148
O3—H3O···O7ⁱⁱⁱ	0.82	2.11	2.741 (4)	134
O3—H3O···O4	0.82	2.41	2.779 (4)	109
O8—H8A···O1	0.82	2.59	2.966 (5)	109

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁ClO₇·C₂H₆O
M_r	466.90
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	292
a, b, c (Å)	11.000 (5), 7.712 (3), 13.213 (4)
β (°)	92.08 (2)
V (Å³)	1120.2 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.48 × 0.44 × 0.36

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	For a sphere [WinGX; Farrugia, 1999)]
T_min, T_max	0.903, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	2921, 2815, 2305
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.143, 1.10
No. of reflections	2815
No. of parameters	281
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.30
Absolute structure	Flack (1983), 562 Friedel pairs
Absolute structure parameter	0.14 (12)

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3ⁱ	0.82	2.02	2.809 (4)	160.1
O4—H4O···O2ⁱⁱ	0.82	1.88	2.694 (4)	171.0
O5—H5O···O8ⁱⁱ	0.82	1.97	2.696 (5)	147.9

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

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Chen, W. S., Lu, S. D. & Breitmaier, E. (1981). Liebigs Ann. Chem. pp. 1893–1895. Google Scholar
Fan, B., Li, J.-L., Li, Y. & Yin, S.-F. (2007). Chin. J. Org. Chem. 27, 1150–1154. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh meeting. Abstract PA 104. Google Scholar
Sha, J. Z. & Mao, H. K. (1987). Chin. Pharm. Bull. 22, 27–30. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

E-[4-(β-D-Allo­pyranos­yl­oxy)phen­yl]-1-(4-chloro­phen­yl)prop-2-enone ethanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

E-[4-(β-D-Allopyranosyloxy)phenyl]-1-(4-chlorophenyl)prop-2-enone ethanol solvate