E-[4-(β-d-Allopyranos-yloxy)phen-yl]-1-(4-chloro-phen-yl)prop-2-enone ethanol solvate.

The title compound, C(21)H(21)ClO(7)·C(2)H(5)OH was synthesized by the condensation reaction between helicid [systematic name: 4-(β-d-allopyranos-yloxy)benzaldehyde] and 4-chloro-aceto-phen-one in ethanol. In the mol-ecular structure, the pyran-oside ring adopts a chair conformation. In the crystal structure, the molecules are linked by inter-molecular O-H⋯O hydrogen bonds involving the OH groups from the pyran-oside unit and from the ethanol solvent mol-ecule.

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 = 466.90

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.143

S = 1.10

2815 reflections

281 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 562 Friedel pairs

Flack parameter: 0.14 (12)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H21ClO7·C2H6O	F(000) = 492
Mr = 466.90	Dx = 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

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

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(Fo2) + (0.099P)2 + 0.0279P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.143	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.43 e Å−3
2815 reflections	Δρmin = −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	Flack parameter: 0.14 (12)

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .