(E)-3-(4-Hydr­oxy-3-methoxy­benzyl­idene)-4-(4-hydroxy­phen­yl)pyrrolidin-2-one

Zhou, Y.-F.; Wang, X.-B.; Qi, J.; Yu, B.-Y.

doi:10.1107/S1600536808008581

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o814

doi:10.1107/S1600536808008581

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(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin-2-one

Yi-Feng Zhou,^a Xiao-Bing Wang,^b Jin Qi ^a and Bo-Yang Yu ^a ^*

^aDepartment of Complex Prescription of TCM, China Pharmaceutical University, Nanjing 210038, People's Republic of China, and ^bDepartment of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, 210009, People's Republic of China
^*Correspondence e-mail: boyangyu59@163.com

(Received 28 February 2008; accepted 31 March 2008; online 10 April 2008)

The title compound, C₁₈H₁₇NO₄, was isolated from an ethanol extract of Ophiopogon japonicus. The dihedral angle between the 4-hydroxy-3-methoxyphenyl ring and the pyrrolidine ring is 17.4 (1)°. The 4-hydroxyphenyl ring makes a dihedral angle of 69.74 (6)° with the least-squares plane through the 4-hydroxy-3-methoxyphenyl ring and the pyrrolidine ring. The conformation of the pyrrolidine fragment is similar to a T-form. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the chemical components and pharmacological properties of the plant Ophiopogon japonicus, see: Anh et al. (2003 ); Kou et al. (2005 ) & Yu (2007 ). For related literature, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₇NO₄
M_r = 311.33
Monoclinic, P 2₁ /c
a = 6.388 (1) Å
b = 14.520 (2) Å
c = 16.880 (2) Å
β = 96.514 (2)°
V = 1555.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.47 × 0.42 × 0.35 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.954, T_max = 0.969
9225 measured reflections
3387 independent reflections
1756 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.137
S = 1.02
3387 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.22 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
N—H1⋯O1ⁱ	0.86	2.09	2.948 (2)	172
O2—H2⋯O1ⁱⁱ	0.82	1.95	2.675 (2)	147
O4—H4⋯O2ⁱⁱⁱ	0.82	2.00	2.721 (2)	147
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT; data reduction: SAINT (Bruker, 2001); 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 I, global. DOI: 10.1107/S1600536808008581/lx2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008581/lx2053Isup2.hkl

checkCIF report

Comment top

The plant of Ophiopogon japonicus (L. f.) Ker-Gawl.(Liliaceae) is widely distributed in South-east Asia, especially in most areaof China, and its tuber root as a famous traditional medicine are widely usedin China to cure acute and chronic inflammation and cardiovascular diseasesincluding thrombotic diseases for thousands of years (Yu, 2007; Kou, et al., 2005). Chemical studies have shown that this plant includes steroidal saponins, homoisoflavonoids andmonoterpene glycosides etc (Anh, et al., 2003). Herein we report the molecular and crystal structure of the title compound (Fig.1), which was isolated from an ethanol extract of the plant of Ophiopogon japonicus.

The main components of the title compound were two aromatic rings, A(C5—C10) and B(C12—C17) and a pyrrolidine ring C(N1/C1—C4) as shown in Fig. 1. Fig. 2 presents the packing diagram of the title compound. Paired molecules at the inversional position assembled via supromolecular sython R₂²(8) (Bernstein, et al., 1995) which consist of hydrogen bonds N1—H1···O1ⁱ, O2—H2···O1ⁱⁱ and O4—H4···O2ⁱⁱⁱ (Symmetry code as in Fig. 2.).

Related literature top

For the chemical components and pharmacological properties of the plant Ophiopogon japonicus, see: Anh et al. (2003); Kou et al. (2005) & Yu (2007). For related literature, see: Bernstein et al. (1995).

Experimental top

Material from the dried subterranean parts of Ophiopogon japonicus (L. f.) Ker-Gawl.(Liliaceae) (40 kg),collected from Sichuan Province in China, was extracted with hot 60% EtOH (3×3 h) under refluxing. The concentrated extract was subjected to D-101 macroporous resin column chromatography eluted successively with EtOH-H₂O(0:100, 30:70, 90:100) to give three fractions (I-III). The concentratedresidue of fraction III (EtOH-H₂O, 90:10) (330 g) was further dissolved in water, and extractedwith EtOAc and n-BuOH successively. The EtOAc extract (107 g) was loaded onto a silica-gel column (200–300 mesh, 600 g) eluted with a gradientof 100% CHCl₃ to CHCl₃—MeOH (50:50) to give 18 fractions,which was pooled by common thin-layer chromatography characteristics. Fraction9 was subjected to repeated chromatography over silica-gel and Sephadex LH-20columns, gave compound (I) (yield 6 mg, m.p. 518 K). Prismatic crystalssuitable for X-ray studies were grown from MeOH by slow evaporation at roomtemperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. A drawing of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. N—H···O and O—H···O hydrogen bond interactions (dotted lines) in the title compound. [Symmetry code: (i) -x, -y+1, -z+1; (ii) -x, y+1/2, -z+1/2; (iii) -x+1, -y+1, -z.]

(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin- 2-one top

Crystal data top

C₁₈H₁₇NO₄	F(000) = 656
M_r = 311.33	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1858 reflections
a = 6.388 (1) Å	θ = 2.4–23.1°
b = 14.520 (2) Å	µ = 0.09 mm⁻¹
c = 16.880 (2) Å	T = 298 K
β = 96.514 (2)°	Block, colourless
V = 1555.6 (4) Å³	0.47 × 0.42 × 0.35 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3387 independent reflections
Radiation source: fine-focus sealed tube	1756 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −13→18
T_min = 0.954, T_max = 0.969	l = −20→21
9225 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0524P)² + 0.295P] where P = (F_o² + 2F_c²)/3
3387 reflections	(Δ/σ)_max < 0.000
209 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₇NO₄	V = 1555.6 (4) Å³
M_r = 311.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.388 (1) Å	µ = 0.09 mm⁻¹
b = 14.520 (2) Å	T = 298 K
c = 16.880 (2) Å	0.47 × 0.42 × 0.35 mm
β = 96.514 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3387 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	1756 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.969	R_int = 0.041
9225 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
3387 reflections	Δρ_min = −0.20 e Å⁻³
209 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N	0.1955 (3)	0.50621 (13)	0.43227 (10)	0.0407 (5)
H1	0.1694	0.5304	0.4766	0.049*
O1	−0.1146 (2)	0.42888 (11)	0.40852 (9)	0.0482 (4)
O2	0.3756 (3)	0.78432 (11)	0.09921 (11)	0.0678 (6)
H2	0.2621	0.8112	0.0921	0.102*
O3	0.5094 (3)	0.35253 (12)	0.04340 (10)	0.0600 (5)
O4	0.2796 (3)	0.20997 (13)	−0.01836 (11)	0.0762 (6)
H4	0.3957	0.2277	−0.0283	0.114*
C1	0.0580 (4)	0.45390 (14)	0.38830 (13)	0.0372 (5)
C2	0.1463 (3)	0.43166 (15)	0.31329 (12)	0.0358 (5)
C3	0.3493 (3)	0.48408 (15)	0.31322 (12)	0.0382 (5)
H3	0.4610	0.4408	0.3031	0.046*
C4	0.3928 (4)	0.5193 (2)	0.39970 (13)	0.0536 (7)
H4A	0.5045	0.4840	0.4294	0.064*
H4B	0.4325	0.5838	0.4008	0.064*
C5	0.3457 (3)	0.56253 (15)	0.25340 (12)	0.0365 (5)
C6	0.1668 (4)	0.59272 (15)	0.20783 (14)	0.0433 (6)
H6	0.0395	0.5631	0.2121	0.052*
C7	0.1720 (4)	0.66655 (16)	0.15552 (14)	0.0472 (6)
H7	0.0495	0.6858	0.1250	0.057*
C8	0.3594 (4)	0.71071 (16)	0.14939 (14)	0.0476 (6)
C9	0.5397 (4)	0.68061 (18)	0.19335 (17)	0.0562 (7)
H9	0.6671	0.7098	0.1884	0.067*
C10	0.5334 (4)	0.60767 (17)	0.24462 (15)	0.0523 (7)
H10	0.6572	0.5880	0.2741	0.063*
C11	0.0515 (4)	0.37125 (15)	0.26114 (13)	0.0401 (6)
H11	−0.0771	0.3493	0.2741	0.048*
C12	0.1159 (4)	0.33400 (15)	0.18741 (13)	0.0396 (6)
C13	0.2897 (4)	0.36572 (15)	0.15170 (13)	0.0419 (6)
H13	0.3690	0.4145	0.1747	0.050*
C14	0.3449 (4)	0.32596 (16)	0.08338 (13)	0.0431 (6)
C15	0.2293 (4)	0.25225 (17)	0.04909 (14)	0.0507 (7)
C16	0.0567 (4)	0.22166 (18)	0.08261 (15)	0.0619 (8)
H16	−0.0229	0.1732	0.0591	0.074*
C17	−0.0002 (4)	0.26206 (17)	0.15097 (14)	0.0536 (7)
H17	−0.1182	0.2407	0.1729	0.064*
C18	0.6343 (4)	0.4276 (2)	0.07462 (17)	0.0672 (8)
H18A	0.5482	0.4818	0.0749	0.101*
H18B	0.7457	0.4382	0.0420	0.101*
H18C	0.6937	0.4137	0.1281	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0424 (11)	0.0505 (12)	0.0299 (10)	0.0051 (9)	0.0069 (8)	−0.0053 (9)
O1	0.0476 (10)	0.0547 (11)	0.0451 (10)	−0.0041 (8)	0.0177 (8)	−0.0079 (8)
O2	0.0807 (14)	0.0491 (11)	0.0812 (14)	0.0105 (10)	0.0418 (11)	0.0189 (10)
O3	0.0623 (11)	0.0676 (12)	0.0549 (11)	−0.0166 (10)	0.0276 (9)	−0.0155 (9)
O4	0.0992 (15)	0.0755 (13)	0.0612 (12)	−0.0284 (11)	0.0411 (11)	−0.0326 (10)
C1	0.0417 (13)	0.0371 (13)	0.0333 (12)	0.0044 (11)	0.0064 (10)	−0.0001 (10)
C2	0.0380 (12)	0.0397 (13)	0.0300 (12)	0.0038 (10)	0.0053 (10)	0.0047 (10)
C3	0.0396 (13)	0.0456 (14)	0.0298 (12)	0.0048 (11)	0.0053 (10)	−0.0016 (10)
C4	0.0417 (14)	0.085 (2)	0.0340 (14)	−0.0061 (13)	0.0032 (11)	−0.0047 (13)
C5	0.0387 (13)	0.0396 (13)	0.0319 (12)	−0.0006 (10)	0.0071 (10)	−0.0053 (10)
C6	0.0380 (13)	0.0444 (14)	0.0483 (15)	−0.0005 (11)	0.0087 (11)	0.0033 (11)
C7	0.0463 (15)	0.0490 (15)	0.0466 (15)	0.0082 (12)	0.0070 (12)	0.0062 (12)
C8	0.0598 (17)	0.0367 (14)	0.0506 (15)	0.0017 (12)	0.0251 (13)	0.0006 (11)
C9	0.0492 (16)	0.0550 (17)	0.0660 (18)	−0.0134 (13)	0.0137 (14)	0.0001 (14)
C10	0.0410 (15)	0.0613 (17)	0.0540 (16)	−0.0058 (13)	0.0026 (12)	0.0039 (13)
C11	0.0427 (14)	0.0413 (13)	0.0373 (13)	−0.0026 (11)	0.0090 (11)	0.0029 (10)
C12	0.0480 (14)	0.0402 (13)	0.0314 (12)	−0.0016 (11)	0.0077 (10)	−0.0009 (10)
C13	0.0490 (14)	0.0412 (13)	0.0361 (13)	−0.0059 (11)	0.0073 (11)	−0.0052 (10)
C14	0.0497 (14)	0.0435 (14)	0.0376 (13)	−0.0030 (11)	0.0117 (11)	−0.0006 (11)
C15	0.0682 (18)	0.0477 (15)	0.0384 (14)	−0.0065 (13)	0.0164 (13)	−0.0084 (11)
C16	0.079 (2)	0.0590 (18)	0.0512 (16)	−0.0282 (15)	0.0212 (14)	−0.0149 (13)
C17	0.0654 (18)	0.0560 (16)	0.0424 (15)	−0.0190 (13)	0.0198 (13)	−0.0089 (12)
C18	0.0575 (18)	0.079 (2)	0.0671 (19)	−0.0173 (16)	0.0167 (15)	−0.0032 (16)

Geometric parameters (Å, º) top

N—C1	1.323 (3)	C6—H6	0.9300
N—C4	1.444 (3)	C7—C8	1.372 (3)
N—H1	0.8600	C7—H7	0.9300
O1—C1	1.245 (2)	C8—C9	1.369 (3)
O2—C8	1.375 (3)	C9—C10	1.371 (3)
O2—H2	0.8200	C9—H9	0.9300
O3—C14	1.367 (3)	C10—H10	0.9300
O3—C18	1.417 (3)	C11—C12	1.458 (3)
O4—C15	1.364 (3)	C11—H11	0.9300
O4—H4	0.8200	C12—C17	1.384 (3)
C1—C2	1.479 (3)	C12—C13	1.400 (3)
C2—C11	1.338 (3)	C13—C14	1.371 (3)
C2—C3	1.504 (3)	C13—H13	0.9300
C3—C5	1.521 (3)	C14—C15	1.389 (3)
C3—C4	1.542 (3)	C15—C16	1.369 (3)
C3—H3	0.9800	C16—C17	1.379 (3)
C4—H4A	0.9700	C16—H16	0.9300
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.375 (3)	C18—H18A	0.9600
C5—C10	1.389 (3)	C18—H18B	0.9600
C6—C7	1.392 (3)	C18—H18C	0.9600

C1—N—C4	114.5 (2)	C7—C8—O2	122.5 (2)
C1—N—H1	122.8	C8—C9—C10	120.4 (2)
C4—N—H1	122.8	C8—C9—H9	119.8
C8—O2—H2	109.5	C10—C9—H9	119.8
C14—O3—C18	117.7 (2)	C9—C10—C5	121.3 (2)
C15—O4—H4	109.5	C9—C10—H10	119.4
O1—C1—N	124.4 (2)	C5—C10—H10	119.4
O1—C1—C2	127.4 (2)	C2—C11—C12	130.9 (2)
N—C1—C2	108.20 (19)	C2—C11—H11	114.6
C11—C2—C1	121.2 (2)	C12—C11—H11	114.6
C11—C2—C3	131.1 (2)	C17—C12—C13	117.9 (2)
C1—C2—C3	107.6 (2)	C17—C12—C11	118.1 (2)
C2—C3—C5	115.6 (2)	C13—C12—C11	124.0 (2)
C2—C3—C4	103.3 (2)	C14—C13—C12	121.0 (2)
C5—C3—C4	111.6 (2)	C14—C13—H13	119.5
C2—C3—H3	108.7	C12—C13—H13	119.5
C5—C3—H3	108.7	O3—C14—C13	125.6 (2)
C4—C3—H3	108.7	O3—C14—C15	114.4 (2)
N—C4—C3	104.2 (2)	C13—C14—C15	120.0 (2)
N—C4—H4A	110.9	O4—C15—C16	118.4 (2)
C3—C4—H4A	110.9	O4—C15—C14	122.0 (2)
N—C4—H4B	110.9	C16—C15—C14	119.5 (2)
C3—C4—H4B	110.9	C15—C16—C17	120.6 (2)
H4A—C4—H4B	108.9	C15—C16—H16	119.7
C6—C5—C10	117.5 (2)	C17—C16—H16	119.7
C6—C5—C3	124.0 (2)	C16—C17—C12	120.9 (2)
C10—C5—C3	118.4 (2)	C16—C17—H17	119.5
C5—C6—C7	121.5 (2)	C12—C17—H17	119.5
C5—C6—H6	119.2	O3—C18—H18A	109.5
C7—C6—H6	119.2	O3—C18—H18B	109.5
C8—C7—C6	119.4 (2)	H18A—C18—H18B	109.5
C8—C7—H7	120.3	O3—C18—H18C	109.5
C6—C7—H7	120.3	H18A—C18—H18C	109.5
C9—C8—C7	119.8 (2)	H18B—C18—H18C	109.5
C9—C8—O2	117.7 (2)

C4—N—C1—O1	174.6 (2)	O2—C8—C9—C10	179.8 (2)
C4—N—C1—C2	−5.3 (3)	C8—C9—C10—C5	0.0 (4)
O1—C1—C2—C11	−7.4 (4)	C6—C5—C10—C9	1.0 (3)
N—C1—C2—C11	172.5 (2)	C3—C5—C10—C9	−178.1 (2)
O1—C1—C2—C3	175.2 (2)	C1—C2—C11—C12	−175.0 (2)
N—C1—C2—C3	−4.9 (2)	C3—C2—C11—C12	1.8 (4)
C11—C2—C3—C5	72.8 (3)	C2—C11—C12—C17	170.9 (2)
C1—C2—C3—C5	−110.1 (2)	C2—C11—C12—C13	−8.2 (4)
C11—C2—C3—C4	−165.1 (2)	C17—C12—C13—C14	−0.9 (4)
C1—C2—C3—C4	12.0 (2)	C11—C12—C13—C14	178.3 (2)
C1—N—C4—C3	12.9 (3)	C18—O3—C14—C13	−0.1 (4)
C2—C3—C4—N	−14.5 (2)	C18—O3—C14—C15	179.8 (2)
C5—C3—C4—N	110.3 (2)	C12—C13—C14—O3	179.0 (2)
C2—C3—C5—C6	7.3 (3)	C12—C13—C14—C15	−0.8 (4)
C4—C3—C5—C6	−110.3 (2)	O3—C14—C15—O4	0.8 (4)
C2—C3—C5—C10	−173.59 (19)	C13—C14—C15—O4	−179.3 (2)
C4—C3—C5—C10	68.8 (2)	O3—C14—C15—C16	−177.9 (2)
C10—C5—C6—C7	−0.9 (3)	C13—C14—C15—C16	2.0 (4)
C3—C5—C6—C7	178.2 (2)	O4—C15—C16—C17	179.8 (2)
C5—C6—C7—C8	−0.3 (3)	C14—C15—C16—C17	−1.5 (4)
C6—C7—C8—C9	1.4 (4)	C15—C16—C17—C12	−0.3 (4)
C6—C7—C8—O2	−179.7 (2)	C13—C12—C17—C16	1.4 (4)
C7—C8—C9—C10	−1.2 (4)	C11—C12—C17—C16	−177.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···O1ⁱ	0.86	2.09	2.948 (2)	172
O2—H2···O1ⁱⁱ	0.82	1.95	2.675 (2)	147
O4—H4···O2ⁱⁱⁱ	0.82	2.00	2.721 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇NO₄
M_r	311.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	6.388 (1), 14.520 (2), 16.880 (2)
β (°)	96.514 (2)
V (Å³)	1555.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.47 × 0.42 × 0.35

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.954, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	9225, 3387, 1756
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.02
No. of reflections	3387
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H1···O1ⁱ	0.86	2.09	2.948 (2)	172.0
O2—H2···O1ⁱⁱ	0.82	1.95	2.675 (2)	146.7
O4—H4···O2ⁱⁱⁱ	0.82	2.00	2.721 (2)	146.5

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

Acknowledgements

This research was financially supported by the National Natural Science Foundation of China (grant No. 30672603 to Dr Bo-Yang Yu).

References

Anh, N. T. H., Sung, T. V., Porzel, A., Frankeb, K. & Wessjohann, L. A. (2003). Phytochemistry, 62, 1153–1158. PubMed Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kou, J. P., Yu, B. Y. & Xu, Q. (2005). Vasc. Pharmcol, 43, 157–163. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, B. Y. (2007). Chin. J. Nat. Med. , 43, 10–14. CAS Google Scholar

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Volume 64| Part 5| May 2008| Page o814

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

(E)-3-(4-Hydr­­oxy-3-meth­oxy­benzyl­­idene)-4-(4-hy­droxy­phen­yl)pyrrolidin-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-3-(4-Hydroxy-3-methoxybenzylidene)-4-(4-hydroxyphenyl)pyrrolidin-2-one