(E)-3-(4-Hydr-oxy-3-methoxy-benzyl-idene)-4-(4-hydroxy-phen-yl)pyrrolidin-2-one.

The title compound, C(18)H(17)NO(4), 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 inter-molecular 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 = 311.33

Monoclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.02

3387 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008581/lx2053sup1.cif

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

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

C18H17NO4	F000 = 656
Mr = 311.33	Dx = 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 = 2.4–23.1º
b = 14.520 (2) Å	µ = 0.09 mm−1
c = 16.880 (2) Å	T = 298 (2) K
β = 96.514 (2)º	Block, colourless
V = 1555.6 (4) Å3	0.47 × 0.42 × 0.35 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3387 independent reflections
Radiation source: fine-focus sealed tube	1756 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 298(2) K	θmin = 1.9º
φ and ω scans	h = −8→7
Absorption correction: multi-scan(SADABS; Sheldrick, 1999)	k = −13→18
Tmin = 0.954, Tmax = 0.969	l = −20→21
9225 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.295P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.000
3387 reflections	Δρmax = 0.22 e Å−3
209 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .