(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-tri-meth-oxy-phen-yl)acrylonitrile.

In the title compound, C(20)H(17)NO(4), the double bond of the acrylonitrile group separating the 1-benzofuran moiety from the 3,4,5-trimeth-oxy-phenyl ring has Z geometry. The 1-benzofuran groups are π-π stacked with inversion-related counterparts such that the furan ring centroid-centroid distance is 3.804 (5) Å. The dihedral angle between the planes of the trimeth-oxy-phenyl ring and the acrylonitrile group is 24.2 (2)°.

Related literature

For the biological activity, see: Naruto et al. (1983 ▶); Parmar et al. (1988 ▶); Shiba (1996 ▶); Sanna et al. (1999 ▶, 2000 ▶); Ohsumi et al. (1998 ▶); Saczewski et al. (2004 ▶). For similar structures, see: Choi et al. (2007 ▶); Seo et al. (2009 ▶); Sonar et al. (2007 ▶).

Experimental

Crystal data

C20H17NO4

M = 335.35

Monoclinic,

a = 28.0892 (5) Å

b = 6.9555 (1) Å

c = 20.0908 (4) Å

β = 122.678 (1)°

V = 3303.93 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.24 × 0.20 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer

26416 measured reflections

3790 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.186

S = 1.02

3790 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.35 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/S1600536812005831/hg5136sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005831/hg5136Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005831/hg5136Isup3.cml

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

C20H17NO4	F(000) = 1408
Mr = 335.35	Dx = 1.348 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4101 reflections
a = 28.0892 (5) Å	θ = 1.0–27.5°
b = 6.9555 (1) Å	µ = 0.09 mm−1
c = 20.0908 (4) Å	T = 90 K
β = 122.678 (1)°	Block, yellow
V = 3303.93 (10) Å3	0.24 × 0.20 × 0.14 mm
Z = 8

Nonius KappaCCD diffractometer	2183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.085
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
Detector resolution: 9.1 pixels mm-1	h = −35→36
ω scans at fixed χ = 55°	k = −8→9
26416 measured reflections	l = −26→25
3790 independent 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1061P)2] where P = (Fo2 + 2Fc2)/3
3790 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.35 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-value wR and goodness of fit S are based on F2. Conventional R-values 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-values based on F2 are statistically about twice as large as those based on F, and R-values based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.48054 (9)	0.1350 (3)	0.63530 (12)	0.0314 (5)
O1	0.54675 (6)	0.4633 (2)	0.60175 (9)	0.0235 (4)
O2	0.28706 (6)	0.8492 (2)	0.58677 (9)	0.0236 (4)
O3	0.26167 (6)	0.5664 (2)	0.65217 (9)	0.0241 (4)
O4	0.33056 (7)	0.2610 (2)	0.71961 (10)	0.0267 (4)
C1	0.52309 (9)	0.6378 (3)	0.60312 (13)	0.0209 (5)
C2	0.58856 (9)	0.5094 (3)	0.58841 (12)	0.0205 (5)
C3	0.62441 (10)	0.3797 (3)	0.58480 (13)	0.0246 (6)
H3	0.6209	0.2451	0.5890	0.030*
C4	0.66571 (10)	0.4553 (3)	0.57475 (13)	0.0251 (6)
H4	0.6916	0.3717	0.5727	0.030*
C5	0.66959 (10)	0.6539 (4)	0.56754 (13)	0.0261 (6)
H5	0.6984	0.7025	0.5610	0.031*
C6	0.63306 (10)	0.7803 (4)	0.56964 (14)	0.0275 (6)
H6	0.6360	0.9145	0.5637	0.033*
C7	0.59119 (9)	0.7082 (3)	0.58073 (13)	0.0223 (5)
C8	0.54814 (10)	0.7870 (3)	0.59013 (13)	0.0238 (6)
H8	0.5388	0.9192	0.5877	0.029*
C9	0.47910 (9)	0.6394 (3)	0.61858 (13)	0.0224 (5)
H9	0.4655	0.7636	0.6198	0.027*
C10	0.45380 (9)	0.4932 (3)	0.63175 (12)	0.0195 (5)
C11	0.47002 (10)	0.2961 (3)	0.63316 (13)	0.0227 (5)
C12	0.40551 (9)	0.5193 (3)	0.64184 (12)	0.0192 (5)
C13	0.37106 (9)	0.6807 (3)	0.61109 (13)	0.0212 (5)
H13	0.3796	0.7790	0.5863	0.025*
C14	0.32409 (9)	0.6977 (3)	0.61670 (12)	0.0194 (5)
C15	0.31095 (9)	0.5540 (3)	0.65306 (12)	0.0203 (5)
C16	0.34635 (9)	0.3953 (3)	0.68529 (12)	0.0208 (5)
C17	0.39355 (9)	0.3767 (3)	0.68009 (13)	0.0217 (5)
H17	0.4176	0.2678	0.7024	0.026*
C18	0.29675 (10)	0.9924 (3)	0.54421 (13)	0.0260 (6)
H18A	0.3342	1.0497	0.5790	0.039*
H18B	0.2678	1.0926	0.5258	0.039*
H18C	0.2949	0.9330	0.4986	0.039*
C19	0.26949 (10)	0.6446 (4)	0.72368 (14)	0.0314 (6)
H19A	0.2982	0.5697	0.7691	0.047*
H19B	0.2337	0.6388	0.7211	0.047*
H19C	0.2819	0.7787	0.7296	0.047*
C20	0.36866 (10)	0.1064 (3)	0.75978 (14)	0.0260 (6)
H20A	0.3713	0.0270	0.7216	0.039*
H20B	0.3549	0.0278	0.7865	0.039*
H20C	0.4061	0.1578	0.7990	0.039*

	U11	U22	U33	U12	U13	U23
N1	0.0334 (13)	0.0259 (13)	0.0429 (13)	0.0016 (10)	0.0257 (11)	−0.0004 (10)
O1	0.0229 (9)	0.0234 (9)	0.0289 (9)	0.0020 (7)	0.0170 (8)	−0.0005 (7)
O2	0.0240 (9)	0.0228 (9)	0.0273 (9)	0.0060 (7)	0.0161 (8)	0.0043 (7)
O3	0.0194 (9)	0.0304 (10)	0.0251 (9)	0.0007 (7)	0.0136 (7)	−0.0019 (7)
O4	0.0247 (9)	0.0252 (10)	0.0334 (9)	0.0018 (7)	0.0178 (8)	0.0077 (7)
C1	0.0202 (12)	0.0174 (12)	0.0225 (12)	0.0031 (10)	0.0100 (10)	−0.0011 (10)
C2	0.0174 (12)	0.0239 (13)	0.0198 (12)	−0.0016 (10)	0.0097 (10)	−0.0023 (10)
C3	0.0281 (14)	0.0211 (13)	0.0274 (13)	0.0042 (11)	0.0168 (12)	−0.0002 (10)
C4	0.0224 (13)	0.0326 (15)	0.0208 (12)	0.0045 (11)	0.0121 (11)	0.0009 (11)
C5	0.0229 (13)	0.0344 (15)	0.0248 (13)	0.0004 (11)	0.0155 (11)	0.0016 (11)
C6	0.0293 (14)	0.0260 (14)	0.0326 (14)	−0.0035 (11)	0.0203 (12)	−0.0019 (11)
C7	0.0207 (12)	0.0231 (13)	0.0229 (12)	0.0009 (10)	0.0118 (10)	−0.0008 (10)
C8	0.0234 (13)	0.0187 (13)	0.0285 (13)	0.0028 (10)	0.0136 (11)	0.0001 (10)
C9	0.0206 (12)	0.0205 (13)	0.0258 (13)	0.0027 (10)	0.0123 (11)	−0.0033 (10)
C10	0.0204 (12)	0.0186 (12)	0.0193 (11)	0.0021 (10)	0.0107 (10)	−0.0001 (10)
C11	0.0218 (13)	0.0237 (14)	0.0273 (13)	0.0000 (11)	0.0163 (11)	−0.0001 (11)
C12	0.0180 (12)	0.0195 (12)	0.0184 (11)	−0.0021 (10)	0.0086 (10)	−0.0035 (10)
C13	0.0247 (13)	0.0192 (13)	0.0224 (12)	−0.0006 (10)	0.0144 (11)	0.0004 (10)
C14	0.0200 (12)	0.0184 (12)	0.0181 (11)	0.0013 (10)	0.0092 (10)	−0.0016 (9)
C15	0.0183 (12)	0.0229 (13)	0.0193 (12)	−0.0008 (10)	0.0100 (10)	−0.0024 (10)
C16	0.0229 (13)	0.0195 (13)	0.0193 (12)	−0.0038 (10)	0.0109 (11)	0.0001 (10)
C17	0.0215 (12)	0.0190 (13)	0.0204 (12)	0.0029 (10)	0.0086 (10)	0.0027 (10)
C18	0.0267 (13)	0.0260 (14)	0.0256 (13)	0.0037 (11)	0.0142 (11)	0.0023 (11)
C19	0.0293 (14)	0.0412 (16)	0.0279 (14)	0.0019 (12)	0.0181 (12)	−0.0012 (12)
C20	0.0320 (14)	0.0211 (13)	0.0271 (13)	0.0000 (11)	0.0173 (12)	0.0045 (10)

N1—C11	1.154 (3)	C8—H8	0.9500
O1—C2	1.376 (3)	C9—C10	1.346 (3)
O1—C1	1.391 (3)	C9—H9	0.9500
O2—C14	1.371 (3)	C10—C11	1.440 (3)
O2—C18	1.431 (3)	C10—C12	1.487 (3)
O3—C15	1.377 (3)	C12—C13	1.390 (3)
O3—C19	1.438 (3)	C12—C17	1.402 (3)
O4—C16	1.370 (3)	C13—C14	1.388 (3)
O4—C20	1.421 (3)	C13—H13	0.9500
C1—C8	1.356 (3)	C14—C15	1.400 (3)
C1—C9	1.428 (3)	C15—C16	1.390 (3)
C2—C3	1.383 (3)	C16—C17	1.391 (3)
C2—C7	1.397 (3)	C17—H17	0.9500
C3—C4	1.384 (3)	C18—H18A	0.9800
C3—H3	0.9500	C18—H18B	0.9800
C4—C5	1.400 (3)	C18—H18C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.369 (3)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C7	1.403 (3)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—C8	1.430 (3)	C20—H20C	0.9800
C2—O1—C1	105.54 (17)	C13—C12—C10	120.4 (2)
C14—O2—C18	116.95 (17)	C17—C12—C10	119.6 (2)
C15—O3—C19	113.60 (17)	C14—C13—C12	119.8 (2)
C16—O4—C20	116.92 (17)	C14—C13—H13	120.1
C8—C1—O1	111.17 (19)	C12—C13—H13	120.1
C8—C1—C9	129.5 (2)	O2—C14—C13	124.0 (2)
O1—C1—C9	119.36 (19)	O2—C14—C15	115.23 (19)
O1—C2—C3	125.5 (2)	C13—C14—C15	120.8 (2)
O1—C2—C7	110.68 (19)	O3—C15—C16	121.12 (19)
C3—C2—C7	123.8 (2)	O3—C15—C14	119.68 (19)
C2—C3—C4	116.8 (2)	C16—C15—C14	119.1 (2)
C2—C3—H3	121.6	O4—C16—C15	115.57 (19)
C4—C3—H3	121.6	O4—C16—C17	123.7 (2)
C3—C4—C5	120.6 (2)	C15—C16—C17	120.7 (2)
C3—C4—H4	119.7	C16—C17—C12	119.7 (2)
C5—C4—H4	119.7	C16—C17—H17	120.2
C6—C5—C4	122.0 (2)	C12—C17—H17	120.2
C6—C5—H5	119.0	O2—C18—H18A	109.5
C4—C5—H5	119.0	O2—C18—H18B	109.5
C5—C6—C7	118.8 (2)	H18A—C18—H18B	109.5
C5—C6—H6	120.6	O2—C18—H18C	109.5
C7—C6—H6	120.6	H18A—C18—H18C	109.5
C2—C7—C6	118.1 (2)	H18B—C18—H18C	109.5
C2—C7—C8	105.4 (2)	O3—C19—H19A	109.5
C6—C7—C8	136.5 (2)	O3—C19—H19B	109.5
C1—C8—C7	107.2 (2)	H19A—C19—H19B	109.5
C1—C8—H8	126.4	O3—C19—H19C	109.5
C7—C8—H8	126.4	H19A—C19—H19C	109.5
C10—C9—C1	130.3 (2)	H19B—C19—H19C	109.5
C10—C9—H9	114.8	O4—C20—H20A	109.5
C1—C9—H9	114.8	O4—C20—H20B	109.5
C9—C10—C11	121.9 (2)	H20A—C20—H20B	109.5
C9—C10—C12	123.5 (2)	O4—C20—H20C	109.5
C11—C10—C12	114.56 (19)	H20A—C20—H20C	109.5
N1—C11—C10	175.8 (2)	H20B—C20—H20C	109.5
C13—C12—C17	120.0 (2)
C2—O1—C1—C8	0.8 (2)	C9—C10—C12—C17	−159.1 (2)
C2—O1—C1—C9	−177.95 (18)	C11—C10—C12—C17	23.9 (3)
C1—O1—C2—C3	178.0 (2)	C17—C12—C13—C14	−1.6 (3)
C1—O1—C2—C7	−0.5 (2)	C10—C12—C13—C14	176.09 (19)
O1—C2—C3—C4	−176.8 (2)	C18—O2—C14—C13	3.0 (3)
C7—C2—C3—C4	1.5 (3)	C18—O2—C14—C15	−175.70 (18)
C2—C3—C4—C5	−0.9 (3)	C12—C13—C14—O2	−178.6 (2)
C3—C4—C5—C6	−0.4 (4)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C7	1.1 (4)	C19—O3—C15—C16	85.9 (2)
O1—C2—C7—C6	177.78 (19)	C19—O3—C15—C14	−98.1 (2)
C3—C2—C7—C6	−0.8 (3)	O2—C14—C15—O3	4.1 (3)
O1—C2—C7—C8	0.0 (2)	C13—C14—C15—O3	−174.67 (19)
C3—C2—C7—C8	−178.5 (2)	O2—C14—C15—C16	−179.78 (19)
C5—C6—C7—C2	−0.6 (3)	C13—C14—C15—C16	1.5 (3)
C5—C6—C7—C8	176.3 (3)	C20—O4—C16—C15	−174.09 (19)
O1—C1—C8—C7	−0.8 (3)	C20—O4—C16—C17	7.6 (3)
C9—C1—C8—C7	177.8 (2)	O3—C15—C16—O4	−3.8 (3)
C2—C7—C8—C1	0.5 (3)	C14—C15—C16—O4	−179.84 (19)
C6—C7—C8—C1	−176.6 (3)	O3—C15—C16—C17	174.64 (19)
C8—C1—C9—C10	−179.9 (2)	C14—C15—C16—C17	−1.4 (3)
O1—C1—C9—C10	−1.3 (4)	O4—C16—C17—C12	178.18 (19)
C1—C9—C10—C11	0.9 (4)	C15—C16—C17—C12	−0.1 (3)
C1—C9—C10—C12	−175.8 (2)	C13—C12—C17—C16	1.6 (3)
C9—C10—C12—C13	23.2 (3)	C10—C12—C17—C16	−176.07 (19)
C11—C10—C12—C13	−153.8 (2)