(Z)-2-{2,4-Dimeth-oxy-6-[(E)-4-meth-oxy-styr-yl]benzyl-idene}quinuclidin-3-one.

The crystal structure of the title compound, C(25)H(27)NO(4), shows the presence of a double bond with Z geometry which connects the quinuclidin-3-one ring and the trimeth-oxy-resveratrol moiety. The dihedral angle between the two benzene rings in the stilbene skeleton is 32.80 (8)°.

Related literature

For related biological activity literature, see: Aggarwal et al. (2004 ▶); Pettit et al. (1995 ▶). For related structure–activity studies, see: Cushman et al. (1991 ▶). For related pharmaco­kinetic and pharmacodynamic studies, see: Jeandet et al. (1979 ▶); Trela et al. (1996 ▶).

Experimental

Crystal data

C25H27NO4

M = 405.48

Orthorhombic,

a = 36.1068 (1) Å

b = 6.8748 (1) Å

c = 8.4813 (4) Å

V = 2105.29 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.26 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.978, T max = 0.993

39211 measured reflections

2554 independent reflections

2313 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.090

S = 1.04

2554 reflections

274 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005843/fj2476sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005843/fj2476Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005843/fj2476Isup3.cml

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

C25H27NO4	F(000) = 864
Mr = 405.48	Dx = 1.279 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2806 reflections
a = 36.1068 (1) Å	θ = 1.0–27.5°
b = 6.8748 (1) Å	µ = 0.09 mm−1
c = 8.4813 (4) Å	T = 90 K
V = 2105.29 (10) Å3	Plate, pale yellow
Z = 4	0.26 × 0.20 × 0.08 mm

Nonius KappaCCD diffractometer	2554 independent reflections
Radiation source: fine-focus sealed tube	2313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 9.1 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scans at fixed χ = 55°	h = −46→46
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −8→8
Tmin = 0.978, Tmax = 0.993	l = −10→11
39211 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.055P)2 + 0.423P] where P = (Fo2 + 2Fc2)/3
2554 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 2σ(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
C1	0.38605 (5)	0.0394 (3)	−0.0016 (2)	0.0199 (4)
C2	0.41142 (5)	−0.0668 (3)	−0.0926 (2)	0.0209 (4)
H2	0.4360	−0.0203	−0.1052	0.025*
O3	0.42772 (4)	−0.3314 (2)	−0.25036 (18)	0.0242 (3)
C3	0.40072 (5)	−0.2399 (3)	−0.1643 (2)	0.0208 (4)
C4	0.36460 (5)	−0.3113 (3)	−0.1488 (2)	0.0213 (4)
H4	0.3575	−0.4302	−0.1971	0.026*
O5	0.30344 (4)	−0.2577 (2)	−0.0355 (2)	0.0273 (4)
C5	0.33950 (5)	−0.2038 (3)	−0.0609 (2)	0.0210 (4)
C6	0.34939 (5)	−0.0292 (3)	0.0138 (2)	0.0194 (4)
C7	0.32098 (5)	0.0712 (3)	0.1075 (3)	0.0208 (4)
H7	0.3007	0.1275	0.0524	0.025*
C8	0.32148 (5)	0.0892 (3)	0.2640 (3)	0.0213 (4)
N9	0.34916 (5)	−0.0003 (3)	0.3624 (2)	0.0275 (4)
C10	0.36272 (6)	0.1427 (4)	0.4797 (3)	0.0343 (5)
H10A	0.3752	0.2509	0.4239	0.041*
H10B	0.3812	0.0793	0.5488	0.041*
C11	0.33104 (6)	0.2257 (4)	0.5823 (3)	0.0323 (5)
H11A	0.3354	0.1939	0.6946	0.039*
H11B	0.3301	0.3690	0.5714	0.039*
C12	0.29427 (6)	0.1356 (4)	0.5273 (3)	0.0312 (5)
H12	0.2728	0.1886	0.5883	0.037*
O13	0.26589 (4)	0.2760 (3)	0.2957 (2)	0.0409 (4)
C13	0.29067 (5)	0.1800 (3)	0.3542 (3)	0.0264 (4)
C14	0.29709 (7)	−0.0863 (4)	0.5442 (3)	0.0414 (6)
H14A	0.2742	−0.1482	0.5040	0.050*
H14B	0.2999	−0.1214	0.6567	0.050*
C15	0.33094 (7)	−0.1599 (4)	0.4492 (3)	0.0398 (6)
H15A	0.3490	−0.2202	0.5223	0.048*
H15B	0.3228	−0.2608	0.3736	0.048*
C16	0.39711 (5)	0.2215 (3)	0.0766 (2)	0.0199 (4)
H16	0.3783	0.3145	0.0986	0.024*
C17	0.43187 (5)	0.2647 (3)	0.1187 (3)	0.0206 (4)
H17	0.4502	0.1709	0.0933	0.025*
C18	0.44483 (5)	0.4405 (3)	0.1996 (2)	0.0188 (4)
C19	0.42275 (5)	0.6030 (3)	0.2311 (2)	0.0207 (4)
H19	0.3978	0.6041	0.1954	0.025*
C20	0.43624 (5)	0.7628 (3)	0.3131 (3)	0.0207 (4)
H20	0.4207	0.8714	0.3332	0.025*
O21	0.48955 (3)	0.9124 (2)	0.4451 (2)	0.0257 (3)
C21	0.47287 (5)	0.7621 (3)	0.3656 (2)	0.0201 (4)
C22	0.49550 (5)	0.6031 (3)	0.3342 (2)	0.0215 (4)
H22	0.5205	0.6030	0.3693	0.026*
C23	0.48175 (5)	0.4451 (3)	0.2520 (2)	0.0205 (4)
H23	0.4975	0.3377	0.2305	0.025*
C24	0.29163 (6)	−0.4419 (3)	−0.0932 (3)	0.0346 (6)
H24A	0.2925	−0.4419	−0.2086	0.052*
H24B	0.2662	−0.4669	−0.0583	0.052*
H24C	0.3080	−0.5437	−0.0523	0.052*
C25	0.41767 (6)	−0.5036 (3)	−0.3349 (3)	0.0248 (4)
H25A	0.4101	−0.6047	−0.2601	0.037*
H25B	0.4390	−0.5497	−0.3960	0.037*
H25C	0.3971	−0.4745	−0.4064	0.037*
C26	0.46609 (6)	1.0558 (3)	0.5147 (3)	0.0263 (4)
H26A	0.4526	1.1251	0.4317	0.039*
H26B	0.4812	1.1484	0.5747	0.039*
H26C	0.4484	0.9923	0.5856	0.039*

	U11	U22	U33	U12	U13	U23
C1	0.0212 (9)	0.0204 (9)	0.0179 (9)	0.0000 (7)	−0.0011 (8)	−0.0002 (8)
C2	0.0177 (8)	0.0241 (9)	0.0209 (10)	−0.0021 (7)	0.0001 (7)	−0.0010 (8)
O3	0.0200 (6)	0.0251 (7)	0.0275 (8)	−0.0008 (5)	0.0031 (6)	−0.0089 (6)
C3	0.0211 (9)	0.0230 (9)	0.0184 (10)	0.0023 (7)	0.0002 (8)	−0.0020 (8)
C4	0.0218 (9)	0.0199 (9)	0.0222 (10)	−0.0010 (7)	−0.0013 (8)	−0.0037 (8)
O5	0.0195 (6)	0.0257 (7)	0.0367 (9)	−0.0073 (6)	0.0054 (6)	−0.0102 (7)
C5	0.0186 (8)	0.0233 (9)	0.0210 (10)	−0.0021 (7)	−0.0002 (8)	−0.0020 (8)
C6	0.0197 (9)	0.0202 (9)	0.0185 (9)	−0.0008 (7)	−0.0008 (7)	−0.0007 (8)
C7	0.0184 (8)	0.0192 (9)	0.0247 (10)	−0.0001 (7)	−0.0029 (8)	−0.0018 (9)
C8	0.0169 (8)	0.0207 (9)	0.0261 (10)	0.0024 (7)	−0.0010 (8)	−0.0039 (8)
N9	0.0258 (8)	0.0354 (10)	0.0213 (8)	0.0083 (8)	−0.0045 (8)	−0.0037 (8)
C10	0.0235 (10)	0.0549 (15)	0.0245 (11)	0.0018 (10)	−0.0039 (9)	−0.0091 (11)
C11	0.0255 (10)	0.0474 (13)	0.0242 (11)	0.0016 (9)	−0.0036 (9)	−0.0080 (11)
C12	0.0187 (9)	0.0482 (13)	0.0268 (11)	0.0008 (9)	0.0011 (8)	−0.0106 (11)
O13	0.0304 (8)	0.0562 (11)	0.0363 (9)	0.0215 (8)	−0.0095 (7)	−0.0178 (9)
C13	0.0197 (9)	0.0300 (10)	0.0296 (11)	0.0041 (8)	−0.0040 (9)	−0.0113 (10)
C14	0.0387 (12)	0.0516 (15)	0.0338 (13)	−0.0093 (11)	0.0032 (11)	0.0046 (12)
C15	0.0522 (14)	0.0343 (12)	0.0329 (13)	0.0067 (11)	−0.0044 (12)	0.0053 (11)
C16	0.0214 (9)	0.0202 (9)	0.0182 (9)	−0.0004 (7)	0.0014 (8)	−0.0013 (8)
C17	0.0199 (8)	0.0204 (9)	0.0214 (10)	0.0002 (7)	0.0004 (8)	−0.0002 (8)
C18	0.0188 (8)	0.0201 (9)	0.0174 (9)	−0.0023 (7)	0.0019 (7)	−0.0007 (8)
C19	0.0196 (8)	0.0226 (10)	0.0199 (10)	−0.0015 (7)	−0.0019 (7)	0.0003 (8)
C20	0.0202 (8)	0.0198 (9)	0.0221 (10)	0.0020 (7)	0.0003 (8)	−0.0011 (8)
O21	0.0209 (6)	0.0221 (7)	0.0342 (8)	−0.0006 (5)	−0.0030 (6)	−0.0099 (7)
C21	0.0216 (9)	0.0193 (9)	0.0193 (9)	−0.0041 (7)	−0.0008 (8)	−0.0027 (8)
C22	0.0173 (8)	0.0241 (9)	0.0230 (10)	−0.0013 (7)	−0.0013 (8)	0.0001 (9)
C23	0.0192 (8)	0.0203 (9)	0.0220 (9)	0.0008 (7)	0.0015 (8)	−0.0020 (8)
C24	0.0294 (10)	0.0271 (11)	0.0473 (15)	−0.0112 (8)	0.0071 (10)	−0.0119 (11)
C25	0.0264 (9)	0.0228 (10)	0.0251 (11)	0.0009 (8)	−0.0007 (9)	−0.0072 (9)
C26	0.0291 (10)	0.0222 (10)	0.0275 (11)	0.0026 (8)	−0.0022 (9)	−0.0069 (9)

C1—C2	1.403 (3)	C14—C15	1.549 (4)
C1—C6	1.411 (3)	C14—H14A	0.9900
C1—C16	1.472 (3)	C14—H14B	0.9900
C2—C3	1.391 (3)	C15—H15A	0.9900
C2—H2	0.9500	C15—H15B	0.9900
O3—C3	1.371 (2)	C16—C17	1.338 (3)
O3—C25	1.431 (2)	C16—H16	0.9500
C3—C4	1.400 (3)	C17—C18	1.466 (3)
C4—C5	1.387 (3)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.398 (3)
O5—C5	1.371 (2)	C18—C23	1.405 (3)
O5—C24	1.422 (2)	C19—C20	1.388 (3)
C5—C6	1.403 (3)	C19—H19	0.9500
C6—C7	1.470 (3)	C20—C21	1.395 (3)
C7—C8	1.333 (3)	C20—H20	0.9500
C7—H7	0.9500	O21—C21	1.373 (2)
C8—N9	1.440 (3)	O21—C26	1.428 (2)
C8—C13	1.488 (3)	C21—C22	1.391 (3)
N9—C15	1.476 (3)	C22—C23	1.383 (3)
N9—C10	1.482 (3)	C22—H22	0.9500
C10—C11	1.546 (3)	C23—H23	0.9500
C10—H10A	0.9900	C24—H24A	0.9800
C10—H10B	0.9900	C24—H24B	0.9800
C11—C12	1.538 (3)	C24—H24C	0.9800
C11—H11A	0.9900	C25—H25A	0.9800
C11—H11B	0.9900	C25—H25B	0.9800
C12—C13	1.505 (3)	C25—H25C	0.9800
C12—C14	1.536 (4)	C26—H26A	0.9800
C12—H12	1.0000	C26—H26B	0.9800
O13—C13	1.217 (3)	C26—H26C	0.9800
C2—C1—C6	119.32 (18)	C12—C14—H14B	109.8
C2—C1—C16	120.87 (16)	C15—C14—H14B	109.8
C6—C1—C16	119.81 (17)	H14A—C14—H14B	108.3
C3—C2—C1	120.27 (17)	N9—C15—C14	111.6 (2)
C3—C2—H2	119.9	N9—C15—H15A	109.3
C1—C2—H2	119.9	C14—C15—H15A	109.3
C3—O3—C25	117.78 (15)	N9—C15—H15B	109.3
O3—C3—C2	115.32 (16)	C14—C15—H15B	109.3
O3—C3—C4	123.48 (17)	H15A—C15—H15B	108.0
C2—C3—C4	121.20 (17)	C17—C16—C1	124.32 (17)
C5—C4—C3	118.17 (17)	C17—C16—H16	117.8
C5—C4—H4	120.9	C1—C16—H16	117.8
C3—C4—H4	120.9	C16—C17—C18	127.40 (17)
C5—O5—C24	118.14 (16)	C16—C17—H17	116.3
O5—C5—C4	124.11 (17)	C18—C17—H17	116.3
O5—C5—C6	113.72 (17)	C19—C18—C23	117.55 (17)
C4—C5—C6	122.16 (17)	C19—C18—C17	124.46 (16)
C5—C6—C1	118.86 (17)	C23—C18—C17	117.98 (16)
C5—C6—C7	117.92 (16)	C20—C19—C18	121.85 (17)
C1—C6—C7	123.20 (18)	C20—C19—H19	119.1
C8—C7—C6	124.95 (19)	C18—C19—H19	119.1
C8—C7—H7	117.5	C19—C20—C21	119.34 (18)
C6—C7—H7	117.5	C19—C20—H20	120.3
C7—C8—N9	123.15 (19)	C21—C20—H20	120.3
C7—C8—C13	122.75 (19)	C21—O21—C26	117.55 (14)
N9—C8—C13	113.58 (18)	O21—C21—C22	115.33 (16)
C8—N9—C15	107.31 (17)	O21—C21—C20	124.75 (17)
C8—N9—C10	109.56 (17)	C22—C21—C20	119.89 (17)
C15—N9—C10	107.79 (18)	C23—C22—C21	120.20 (17)
N9—C10—C11	112.23 (17)	C23—C22—H22	119.9
N9—C10—H10A	109.2	C21—C22—H22	119.9
C11—C10—H10A	109.2	C22—C23—C18	121.16 (18)
N9—C10—H10B	109.2	C22—C23—H23	119.4
C11—C10—H10B	109.2	C18—C23—H23	119.4
H10A—C10—H10B	107.9	O5—C24—H24A	109.5
C12—C11—C10	108.62 (18)	O5—C24—H24B	109.5
C12—C11—H11A	110.0	H24A—C24—H24B	109.5
C10—C11—H11A	110.0	O5—C24—H24C	109.5
C12—C11—H11B	110.0	H24A—C24—H24C	109.5
C10—C11—H11B	110.0	H24B—C24—H24C	109.5
H11A—C11—H11B	108.3	O3—C25—H25A	109.5
C13—C12—C14	107.4 (2)	O3—C25—H25B	109.5
C13—C12—C11	106.79 (19)	H25A—C25—H25B	109.5
C14—C12—C11	108.32 (19)	O3—C25—H25C	109.5
C13—C12—H12	111.4	H25A—C25—H25C	109.5
C14—C12—H12	111.4	H25B—C25—H25C	109.5
C11—C12—H12	111.4	O21—C26—H26A	109.5
O13—C13—C8	124.6 (2)	O21—C26—H26B	109.5
O13—C13—C12	124.8 (2)	H26A—C26—H26B	109.5
C8—C13—C12	110.61 (18)	O21—C26—H26C	109.5
C12—C14—C15	109.2 (2)	H26A—C26—H26C	109.5
C12—C14—H14A	109.8	H26B—C26—H26C	109.5
C15—C14—H14A	109.8
C6—C1—C2—C3	−1.2 (3)	C10—C11—C12—C14	59.0 (3)
C16—C1—C2—C3	179.23 (18)	C7—C8—C13—O13	−13.8 (3)
C25—O3—C3—C2	−176.17 (18)	N9—C8—C13—O13	174.2 (2)
C25—O3—C3—C4	3.3 (3)	C7—C8—C13—C12	165.8 (2)
C1—C2—C3—O3	179.94 (18)	N9—C8—C13—C12	−6.2 (3)
C1—C2—C3—C4	0.5 (3)	C14—C12—C13—O13	125.5 (2)
O3—C3—C4—C5	−178.81 (19)	C11—C12—C13—O13	−118.5 (2)
C2—C3—C4—C5	0.6 (3)	C14—C12—C13—C8	−54.1 (2)
C24—O5—C5—C4	4.7 (3)	C11—C12—C13—C8	61.9 (2)
C24—O5—C5—C6	−174.0 (2)	C13—C12—C14—C15	58.5 (3)
C3—C4—C5—O5	−179.51 (19)	C11—C12—C14—C15	−56.5 (3)
C3—C4—C5—C6	−1.0 (3)	C8—N9—C15—C14	−56.1 (3)
O5—C5—C6—C1	178.92 (18)	C10—N9—C15—C14	61.8 (2)
C4—C5—C6—C1	0.2 (3)	C12—C14—C15—N9	−3.7 (3)
O5—C5—C6—C7	0.2 (3)	C2—C1—C16—C17	−25.6 (3)
C4—C5—C6—C7	−178.45 (19)	C6—C1—C16—C17	154.9 (2)
C2—C1—C6—C5	0.9 (3)	C1—C16—C17—C18	−178.61 (19)
C16—C1—C6—C5	−179.58 (18)	C16—C17—C18—C19	−7.2 (3)
C2—C1—C6—C7	179.48 (19)	C16—C17—C18—C23	171.5 (2)
C16—C1—C6—C7	−1.0 (3)	C23—C18—C19—C20	−0.9 (3)
C5—C6—C7—C8	111.4 (2)	C17—C18—C19—C20	177.7 (2)
C1—C6—C7—C8	−67.3 (3)	C18—C19—C20—C21	0.1 (3)
C6—C7—C8—N9	−4.3 (4)	C26—O21—C21—C22	−164.65 (18)
C6—C7—C8—C13	−175.52 (18)	C26—O21—C21—C20	17.1 (3)
C7—C8—N9—C15	−108.9 (2)	C19—C20—C21—O21	178.75 (19)
C13—C8—N9—C15	63.0 (2)	C19—C20—C21—C22	0.6 (3)
C7—C8—N9—C10	134.3 (2)	O21—C21—C22—C23	−178.73 (18)
C13—C8—N9—C10	−53.7 (2)	C20—C21—C22—C23	−0.4 (3)
C8—N9—C10—C11	57.3 (2)	C21—C22—C23—C18	−0.5 (3)
C15—N9—C10—C11	−59.2 (2)	C19—C18—C23—C22	1.1 (3)
N9—C10—C11—C12	−1.3 (3)	C17—C18—C23—C22	−177.61 (19)
C10—C11—C12—C13	−56.4 (2)