(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-tri-methoxy-phen-yl)acrylonitrile.

In the title compound, C(20)H(18)N(2)O(3), the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth-oxy-phenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). Mol-ecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N-H⋯O inter-molecular hydrogen bonds, which form an R(1) (2)(5) motif between the indole NH group and the two meth-oxy O atoms furthest from the nitrile group.

Related literature

For biological activity of similar acrylonitriles, see: Naruto et al. (1983 ▶); Ohsumi et al. (1998 ▶); Saczewski et al. (2004 ▶). For the mol­ecular structures of (E)-3-(benzo[b]thio­phen-2-yl)-2-(3,4,5-trimeth­oxy­phen­yl)acrylonitrile and (Z)-3-(benzo[b]thio­phen-2-yl)-2-(3,4-dimeth­oxy­phen­yl)acrylonitrile, see: Sonar et al. (2007 ▶). For the structure of (Z)-4-[3-(2,5-dioxo­imi­dazol­idin-4-ylidenemeth­yl)-1H-indol-1-ylmeth­yl]benzo­nitrile, see: Penthala et al. (2008 ▶).

Experimental

Crystal data

C20H18N2O3

M = 334.36

Monoclinic,

a = 11.3384 (4) Å

b = 21.1383 (8) Å

c = 6.9570 (3) Å

β = 93.610 (2)°

V = 1664.11 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.74 mm−1

T = 90 K

0.24 × 0.07 × 0.02 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.843, T max = 0.929

20812 measured reflections

2979 independent reflections

2679 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.07

2979 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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/S1600536812005855/nk2125sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005855/nk2125Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005855/nk2125Isup3.cml

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

C20H18N2O3	F(000) = 704
Mr = 334.36	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9970 reflections
a = 11.3384 (4) Å	θ = 3.9–68.1°
b = 21.1383 (8) Å	µ = 0.74 mm−1
c = 6.9570 (3) Å	T = 90 K
β = 93.610 (2)°	Lath, yellow
V = 1664.11 (11) Å3	0.24 × 0.07 × 0.02 mm
Z = 4

Bruker X8 Proteum diffractometer	2979 independent reflections
Radiation source: fine-focus rotating anode	2679 reflections with I > 2σ(I)
Graded multilayer optics monochromator	Rint = 0.053
Detector resolution: 5.6 pixels mm-1	θmax = 68.1°, θmin = 3.9°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2006)	k = −25→25
Tmin = 0.843, Tmax = 0.929	l = −7→8
20812 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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.7731P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2979 reflections	Δρmax = 0.26 e Å−3
233 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0016 (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	0.29609 (11)	0.42543 (6)	0.78546 (16)	0.0203 (3)
H1N	0.2929 (15)	0.4617 (8)	0.732 (2)	0.024*
N2	0.68309 (12)	0.37056 (6)	0.89979 (17)	0.0251 (3)
O1	0.91232 (9)	0.14011 (4)	1.03760 (14)	0.0220 (2)
O2	0.79293 (9)	0.03501 (4)	0.91759 (13)	0.0202 (2)
O3	0.56732 (8)	0.03817 (4)	0.81372 (14)	0.0203 (2)
C1	0.38533 (13)	0.38300 (6)	0.77536 (19)	0.0195 (3)
H1	0.4520	0.3883	0.7009	0.023*
C2	0.36515 (12)	0.33101 (6)	0.88911 (18)	0.0177 (3)
C3	0.25524 (12)	0.34334 (6)	0.97547 (18)	0.0172 (3)
C4	0.18967 (13)	0.31113 (6)	1.1088 (2)	0.0206 (3)
H4	0.2151	0.2712	1.1585	0.025*
C5	0.08734 (14)	0.33867 (7)	1.1662 (2)	0.0253 (3)
H5	0.0426	0.3174	1.2574	0.030*
C6	0.04772 (14)	0.39732 (7)	1.0932 (2)	0.0266 (3)
H6	−0.0241	0.4145	1.1335	0.032*
C7	0.11116 (13)	0.43046 (7)	0.9640 (2)	0.0225 (3)
H7	0.0850	0.4704	0.9153	0.027*
C8	0.21522 (13)	0.40300 (6)	0.90769 (19)	0.0188 (3)
C9	0.43611 (12)	0.27458 (6)	0.91389 (18)	0.0175 (3)
H9	0.3947	0.2367	0.9389	0.021*
C10	0.55447 (13)	0.26926 (6)	0.90571 (18)	0.0170 (3)
C11	0.61787 (12)	0.20801 (6)	0.91199 (18)	0.0166 (3)
C12	0.73704 (12)	0.20546 (6)	0.97301 (18)	0.0173 (3)
H12	0.7781	0.2431	1.0103	0.021*
C13	0.79597 (12)	0.14770 (6)	0.97940 (18)	0.0173 (3)
C14	0.73641 (12)	0.09257 (6)	0.92416 (18)	0.0166 (3)
C15	0.61699 (12)	0.09519 (6)	0.86363 (18)	0.0166 (3)
C16	0.55781 (12)	0.15264 (6)	0.85555 (18)	0.0163 (3)
H16	0.4768	0.1544	0.8118	0.020*
C17	0.62542 (13)	0.32580 (6)	0.89881 (18)	0.0185 (3)
C18	0.96763 (14)	0.19066 (7)	1.1428 (2)	0.0263 (3)
H18A	0.9721	0.2277	1.0590	0.039*
H18B	1.0476	0.1780	1.1892	0.039*
H18C	0.9214	0.2012	1.2529	0.039*
C19	0.84428 (13)	0.01136 (7)	1.0993 (2)	0.0242 (3)
H19A	0.9256	0.0269	1.1196	0.036*
H19B	0.8445	−0.0350	1.0971	0.036*
H19C	0.7976	0.0262	1.2042	0.036*
C20	0.44638 (13)	0.03775 (7)	0.7438 (2)	0.0227 (3)
H20A	0.3972	0.0538	0.8440	0.034*
H20B	0.4225	−0.0056	0.7100	0.034*
H20C	0.4363	0.0648	0.6295	0.034*

	U11	U22	U33	U12	U13	U23
N1	0.0269 (7)	0.0156 (6)	0.0183 (6)	0.0011 (5)	−0.0004 (5)	0.0033 (5)
N2	0.0311 (7)	0.0229 (7)	0.0218 (6)	−0.0038 (5)	0.0048 (5)	−0.0011 (5)
O1	0.0174 (5)	0.0210 (5)	0.0270 (5)	−0.0010 (4)	−0.0031 (4)	−0.0036 (4)
O2	0.0221 (5)	0.0176 (5)	0.0202 (5)	0.0035 (4)	−0.0040 (4)	−0.0021 (4)
O3	0.0198 (5)	0.0160 (5)	0.0245 (5)	−0.0015 (4)	−0.0042 (4)	−0.0019 (4)
C1	0.0237 (8)	0.0196 (7)	0.0153 (6)	0.0002 (6)	0.0008 (6)	0.0000 (5)
C2	0.0222 (7)	0.0176 (7)	0.0131 (6)	−0.0018 (5)	−0.0017 (5)	−0.0013 (5)
C3	0.0196 (7)	0.0160 (7)	0.0153 (6)	−0.0018 (5)	−0.0030 (5)	−0.0031 (5)
C4	0.0240 (8)	0.0172 (7)	0.0205 (7)	−0.0027 (6)	−0.0007 (6)	−0.0008 (5)
C5	0.0271 (8)	0.0232 (7)	0.0262 (8)	−0.0059 (6)	0.0074 (6)	−0.0054 (6)
C6	0.0227 (8)	0.0252 (8)	0.0320 (8)	−0.0002 (6)	0.0034 (6)	−0.0095 (6)
C7	0.0230 (8)	0.0181 (7)	0.0257 (7)	0.0025 (6)	−0.0046 (6)	−0.0054 (5)
C8	0.0223 (7)	0.0169 (7)	0.0167 (6)	−0.0014 (5)	−0.0030 (6)	−0.0027 (5)
C9	0.0241 (8)	0.0166 (7)	0.0118 (6)	−0.0017 (5)	0.0006 (5)	−0.0002 (5)
C10	0.0238 (8)	0.0174 (7)	0.0098 (6)	−0.0011 (5)	0.0007 (5)	0.0003 (5)
C11	0.0225 (7)	0.0182 (7)	0.0095 (6)	0.0004 (5)	0.0035 (5)	0.0014 (5)
C12	0.0214 (7)	0.0173 (7)	0.0133 (6)	−0.0028 (5)	0.0014 (5)	−0.0006 (5)
C13	0.0184 (7)	0.0220 (7)	0.0116 (6)	−0.0010 (5)	0.0005 (5)	0.0007 (5)
C14	0.0206 (7)	0.0166 (7)	0.0125 (6)	0.0020 (5)	0.0005 (5)	−0.0003 (5)
C15	0.0218 (7)	0.0169 (7)	0.0110 (6)	−0.0023 (5)	0.0007 (5)	−0.0004 (5)
C16	0.0178 (7)	0.0195 (7)	0.0115 (6)	0.0011 (5)	−0.0001 (5)	0.0010 (5)
C17	0.0230 (7)	0.0202 (7)	0.0124 (6)	0.0035 (6)	0.0024 (5)	−0.0006 (5)
C18	0.0250 (8)	0.0240 (8)	0.0288 (8)	−0.0042 (6)	−0.0060 (6)	−0.0033 (6)
C19	0.0243 (8)	0.0216 (7)	0.0257 (7)	0.0022 (6)	−0.0062 (6)	0.0033 (6)
C20	0.0201 (8)	0.0210 (7)	0.0261 (7)	−0.0018 (6)	−0.0050 (6)	−0.0013 (6)

N1—C1	1.3572 (19)	C7—H7	0.9500
N1—C8	1.3737 (19)	C9—C10	1.351 (2)
N1—H1N	0.851 (18)	C9—H9	0.9500
N2—C17	1.1499 (19)	C10—C17	1.4433 (19)
O1—C13	1.3649 (17)	C10—C11	1.4801 (18)
O1—C18	1.4188 (17)	C11—C12	1.392 (2)
O2—C14	1.3773 (16)	C11—C16	1.3980 (19)
O2—C19	1.4472 (17)	C12—C13	1.3910 (19)
O3—C15	1.3661 (16)	C12—H12	0.9500
O3—C20	1.4257 (17)	C13—C14	1.3890 (19)
C1—C2	1.3818 (19)	C14—C15	1.394 (2)
C1—H1	0.9500	C15—C16	1.3868 (19)
C2—C3	1.4409 (19)	C16—H16	0.9500
C2—C9	1.4430 (19)	C18—H18A	0.9800
C3—C4	1.4011 (19)	C18—H18B	0.9800
C3—C8	1.4113 (19)	C18—H18C	0.9800
C4—C5	1.380 (2)	C19—H19A	0.9800
C4—H4	0.9500	C19—H19B	0.9800
C5—C6	1.403 (2)	C19—H19C	0.9800
C5—H5	0.9500	C20—H20A	0.9800
C6—C7	1.377 (2)	C20—H20B	0.9800
C6—H6	0.9500	C20—H20C	0.9800
C7—C8	1.393 (2)
C1—N1—C8	109.44 (12)	C12—C11—C10	120.23 (12)
C1—N1—H1N	125.7 (11)	C16—C11—C10	119.80 (13)
C8—N1—H1N	124.7 (11)	C13—C12—C11	119.93 (12)
C13—O1—C18	116.87 (11)	C13—C12—H12	120.0
C14—O2—C19	116.02 (10)	C11—C12—H12	120.0
C15—O3—C20	117.67 (11)	O1—C13—C14	115.30 (12)
N1—C1—C2	110.19 (12)	O1—C13—C12	124.47 (12)
N1—C1—H1	124.9	C14—C13—C12	120.23 (13)
C2—C1—H1	124.9	O2—C14—C13	122.10 (12)
C1—C2—C3	105.88 (12)	O2—C14—C15	118.06 (12)
C1—C2—C9	127.93 (13)	C13—C14—C15	119.76 (12)
C3—C2—C9	126.16 (12)	O3—C15—C16	124.87 (13)
C4—C3—C8	118.85 (13)	O3—C15—C14	114.77 (11)
C4—C3—C2	134.18 (13)	C16—C15—C14	120.36 (12)
C8—C3—C2	106.90 (12)	C15—C16—C11	119.73 (13)
C5—C4—C3	118.52 (13)	C15—C16—H16	120.1
C5—C4—H4	120.7	C11—C16—H16	120.1
C3—C4—H4	120.7	N2—C17—C10	177.68 (14)
C4—C5—C6	121.61 (13)	O1—C18—H18A	109.5
C4—C5—H5	119.2	O1—C18—H18B	109.5
C6—C5—H5	119.2	H18A—C18—H18B	109.5
C7—C6—C5	121.15 (14)	O1—C18—H18C	109.5
C7—C6—H6	119.4	H18A—C18—H18C	109.5
C5—C6—H6	119.4	H18B—C18—H18C	109.5
C6—C7—C8	117.25 (13)	O2—C19—H19A	109.5
C6—C7—H7	121.4	O2—C19—H19B	109.5
C8—C7—H7	121.4	H19A—C19—H19B	109.5
N1—C8—C7	129.82 (13)	O2—C19—H19C	109.5
N1—C8—C3	107.59 (12)	H19A—C19—H19C	109.5
C7—C8—C3	122.59 (13)	H19B—C19—H19C	109.5
C10—C9—C2	127.70 (13)	O3—C20—H20A	109.5
C10—C9—H9	116.1	O3—C20—H20B	109.5
C2—C9—H9	116.1	H20A—C20—H20B	109.5
C9—C10—C17	119.30 (12)	O3—C20—H20C	109.5
C9—C10—C11	123.60 (12)	H20A—C20—H20C	109.5
C17—C10—C11	117.04 (12)	H20B—C20—H20C	109.5
C12—C11—C16	119.97 (12)
C8—N1—C1—C2	0.67 (16)	C9—C10—C11—C16	23.89 (19)
N1—C1—C2—C3	−0.36 (15)	C17—C10—C11—C16	−158.85 (12)
N1—C1—C2—C9	177.84 (13)	C16—C11—C12—C13	−0.58 (18)
C1—C2—C3—C4	−176.92 (15)	C10—C11—C12—C13	179.70 (11)
C9—C2—C3—C4	4.8 (2)	C18—O1—C13—C14	−163.42 (12)
C1—C2—C3—C8	−0.07 (15)	C18—O1—C13—C12	16.64 (18)
C9—C2—C3—C8	−178.31 (13)	C11—C12—C13—O1	−179.74 (11)
C8—C3—C4—C5	1.0 (2)	C11—C12—C13—C14	0.32 (19)
C2—C3—C4—C5	177.59 (14)	C19—O2—C14—C13	62.90 (16)
C3—C4—C5—C6	0.6 (2)	C19—O2—C14—C15	−120.39 (13)
C4—C5—C6—C7	−1.5 (2)	O1—C13—C14—O2	−3.80 (18)
C5—C6—C7—C8	0.7 (2)	C12—C13—C14—O2	176.14 (11)
C1—N1—C8—C7	179.00 (14)	O1—C13—C14—C15	179.55 (11)
C1—N1—C8—C3	−0.69 (15)	C12—C13—C14—C15	−0.51 (19)
C6—C7—C8—N1	−178.69 (14)	C20—O3—C15—C16	1.54 (18)
C6—C7—C8—C3	1.0 (2)	C20—O3—C15—C14	−177.79 (11)
C4—C3—C8—N1	177.88 (12)	O2—C14—C15—O3	3.54 (17)
C2—C3—C8—N1	0.46 (15)	C13—C14—C15—O3	−179.67 (11)
C4—C3—C8—C7	−1.8 (2)	O2—C14—C15—C16	−175.82 (11)
C2—C3—C8—C7	−179.26 (13)	C13—C14—C15—C16	0.97 (19)
C1—C2—C9—C10	31.1 (2)	O3—C15—C16—C11	179.48 (11)
C3—C2—C9—C10	−151.04 (14)	C14—C15—C16—C11	−1.22 (18)
C2—C9—C10—C17	9.7 (2)	C12—C11—C16—C15	1.03 (18)
C2—C9—C10—C11	−173.07 (12)	C10—C11—C16—C15	−179.25 (11)
C9—C10—C11—C12	−156.39 (13)	C9—C10—C17—N2	103 (4)
C17—C10—C11—C12	20.87 (17)	C11—C10—C17—N2	−74 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.851 (18)	2.075 (18)	2.8635 (15)	153.8 (16)
N1—H1N···O3i	0.851 (18)	2.301 (17)	2.9476 (15)	133.0 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.851 (18)	2.075 (18)	2.8635 (15)	153.8 (16)
N1—H1N⋯O3i	0.851 (18)	2.301 (17)	2.9476 (15)	133.0 (15)

Symmetry code: (i) .