(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemeth-yl)-1H-indol-1-ylmeth-yl]benzonitrile.

In the title compound, C(20)H(14)N(4)O(2), mol-ecules are linked into chains by N-H⋯O hydrogen bonds, but the cyano group does not participate in the supra-molecular aggregation. The crystal structure of the compound indicates the presence of a double bond with Z geometry, connecting the imidazolidine and indole units. The dihedral angle between the imidazole and benzene ring planes is 62.45 (4)°.

Related literature

For 2-indol-3-yl-methyl­enequinuclidin-3-ols NADPH oxidase activity, see: Sekhar et al. (2003 ▶). For novel substituted (Z)-2-(N-benzyl­indol-3-ylmethyl­ene)quinuclidin-3-one and (Z)-(±)-2-(N-benzyl­indol-3-ylmethyl­ene)quinuclidin-3-ol derivatives as potent thermal sensitizing agents, see: Sonar et al. (2007 ▶). For the mol­ecular structures of di- and triindolyl­methanes, see: Mason et al. (2003 ▶). For the structures of 1H-indole-3-ethyl­ene-3′-methoxy­salicylaldimine and 3-[3′-aza­pentyl-3′-en-4′-(2′′-hydroxy­phen­yl)]indole, see: Zarza et al. (1988 ▶).

Experimental

Crystal data

C20H14N4O2

M = 342.35

Monoclinic,

a = 18.8495 (16) Å

b = 7.6812 (7) Å

c = 24.322 (2) Å

β = 110.939 (3)°

V = 3289.0 (5) Å3

Z = 8

Cu Kα radiation

μ = 0.76 mm−1

T = 90.0 (2) K

0.15 × 0.08 × 0.06 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.806, T max = 0.957

23493 measured reflections

3025 independent reflections

2849 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.04

3025 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 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 datablocks global, I. DOI: 10.1107/S1600536808032601/fj2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032601/fj2156Isup2.hkl

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

C20H14N4O2	F(000) = 1424
Mr = 342.35	Dx = 1.383 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 9981 reflections
a = 18.8495 (16) Å	θ = 3.9–68.8°
b = 7.6812 (7) Å	µ = 0.76 mm−1
c = 24.322 (2) Å	T = 90 K
β = 110.939 (3)°	Block, yellow
V = 3289.0 (5) Å3	0.15 × 0.08 × 0.06 mm
Z = 8

Bruker X8 Proteum diffractometer	3025 independent reflections
Radiation source: fine-focus rotating anode	2849 reflections with I > 2σ(I)
graded multilayer optics	Rint = 0.039
Detector resolution: 18 pixels mm-1	θmax = 68.8°, θmin = 3.9°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2006)	k = −9→9
Tmin = 0.806, Tmax = 0.957	l = −28→29
23493 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.043P)2 + 2.7005P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3025 reflections	Δρmax = 0.24 e Å−3
236 parameters	Δρmin = −0.30 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: 0.00030 (6)

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
N1	0.41106 (5)	0.49108 (13)	0.60476 (4)	0.0204 (2)
N2	0.28685 (7)	0.12998 (16)	0.84996 (5)	0.0344 (3)
N3	0.66684 (5)	0.16845 (13)	0.50768 (4)	0.0204 (2)
H3	0.7010	0.1248	0.4946	0.024*
N4	0.56545 (5)	0.18829 (13)	0.53212 (4)	0.0213 (2)
H4	0.5232	0.1612	0.5377	0.026*
O1	0.71827 (4)	0.44259 (11)	0.53352 (4)	0.0233 (2)
O2	0.58759 (5)	−0.07063 (12)	0.49259 (4)	0.0300 (2)
C1	0.46081 (6)	0.41065 (15)	0.58406 (5)	0.0196 (2)
H1	0.4549	0.2960	0.5684	0.024*
C2	0.52091 (6)	0.51930 (15)	0.58903 (5)	0.0185 (2)
C3	0.50688 (6)	0.67773 (15)	0.61526 (5)	0.0201 (2)
C4	0.54595 (7)	0.83512 (16)	0.63133 (6)	0.0269 (3)
H4A	0.5928	0.8535	0.6257	0.032*
C5	0.51500 (8)	0.96293 (17)	0.65546 (7)	0.0343 (3)
H5	0.5412	1.0703	0.6668	0.041*
C6	0.44596 (8)	0.93872 (17)	0.66367 (6)	0.0337 (3)
H6	0.4263	1.0298	0.6805	0.040*
C7	0.40588 (7)	0.78571 (17)	0.64794 (6)	0.0271 (3)
H7	0.3587	0.7693	0.6531	0.033*
C8	0.43762 (6)	0.65602 (15)	0.62406 (5)	0.0210 (3)
C9	0.33815 (6)	0.41858 (17)	0.60065 (5)	0.0235 (3)
H9A	0.3245	0.3259	0.5704	0.028*
H9B	0.2993	0.5112	0.5869	0.028*
C10	0.33468 (6)	0.34369 (15)	0.65670 (5)	0.0199 (3)
C11	0.27885 (7)	0.22088 (16)	0.65210 (5)	0.0245 (3)
H11	0.2487	0.1771	0.6145	0.029*
C12	0.26669 (7)	0.16176 (16)	0.70142 (6)	0.0264 (3)
H12	0.2280	0.0786	0.6979	0.032*
C13	0.31168 (7)	0.22512 (15)	0.75657 (5)	0.0225 (3)
C14	0.36964 (7)	0.34280 (15)	0.76188 (5)	0.0222 (3)
H14	0.4013	0.3830	0.7996	0.027*
C15	0.38107 (6)	0.40105 (15)	0.71200 (5)	0.0216 (3)
H15	0.4209	0.4809	0.7155	0.026*
C16	0.29783 (7)	0.17006 (16)	0.80831 (5)	0.0266 (3)
C17	0.58384 (6)	0.49104 (15)	0.57005 (5)	0.0194 (2)
H17	0.6177	0.5866	0.5755	0.023*
C18	0.60159 (6)	0.34914 (15)	0.54582 (5)	0.0186 (2)
C19	0.66927 (6)	0.33333 (15)	0.52922 (5)	0.0190 (2)
C20	0.60397 (6)	0.07873 (16)	0.50901 (5)	0.0220 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0187 (5)	0.0246 (5)	0.0217 (5)	−0.0014 (4)	0.0117 (4)	−0.0015 (4)
N2	0.0372 (6)	0.0407 (7)	0.0285 (6)	−0.0136 (5)	0.0156 (5)	−0.0019 (5)
N3	0.0167 (5)	0.0266 (5)	0.0216 (5)	−0.0027 (4)	0.0116 (4)	−0.0056 (4)
N4	0.0171 (5)	0.0257 (5)	0.0260 (5)	−0.0045 (4)	0.0137 (4)	−0.0056 (4)
O1	0.0205 (4)	0.0268 (4)	0.0277 (4)	−0.0048 (3)	0.0148 (3)	−0.0036 (3)
O2	0.0242 (4)	0.0301 (5)	0.0419 (5)	−0.0081 (4)	0.0195 (4)	−0.0151 (4)
C1	0.0207 (5)	0.0222 (6)	0.0190 (5)	0.0000 (4)	0.0109 (4)	−0.0021 (4)
C2	0.0182 (5)	0.0215 (6)	0.0168 (5)	0.0010 (4)	0.0076 (4)	0.0007 (4)
C3	0.0206 (6)	0.0215 (6)	0.0198 (5)	0.0015 (4)	0.0091 (4)	0.0025 (4)
C4	0.0268 (6)	0.0223 (6)	0.0354 (7)	−0.0011 (5)	0.0156 (5)	0.0008 (5)
C5	0.0384 (7)	0.0207 (6)	0.0477 (8)	−0.0023 (5)	0.0201 (6)	−0.0046 (6)
C6	0.0387 (8)	0.0240 (7)	0.0440 (8)	0.0065 (5)	0.0215 (6)	−0.0037 (6)
C7	0.0270 (6)	0.0275 (6)	0.0318 (7)	0.0052 (5)	0.0166 (5)	0.0017 (5)
C8	0.0217 (6)	0.0218 (6)	0.0213 (6)	0.0019 (4)	0.0100 (5)	0.0022 (4)
C9	0.0181 (5)	0.0327 (7)	0.0223 (6)	−0.0031 (5)	0.0104 (5)	−0.0015 (5)
C10	0.0180 (5)	0.0214 (6)	0.0237 (6)	0.0021 (4)	0.0115 (5)	−0.0017 (4)
C11	0.0230 (6)	0.0280 (6)	0.0239 (6)	−0.0048 (5)	0.0102 (5)	−0.0050 (5)
C12	0.0255 (6)	0.0272 (6)	0.0296 (6)	−0.0080 (5)	0.0137 (5)	−0.0026 (5)
C13	0.0242 (6)	0.0225 (6)	0.0242 (6)	0.0004 (5)	0.0128 (5)	0.0012 (5)
C14	0.0228 (6)	0.0219 (6)	0.0222 (6)	−0.0005 (4)	0.0083 (5)	−0.0016 (4)
C15	0.0192 (5)	0.0216 (6)	0.0255 (6)	−0.0021 (4)	0.0100 (5)	−0.0005 (5)
C16	0.0270 (6)	0.0277 (6)	0.0267 (6)	−0.0060 (5)	0.0118 (5)	−0.0018 (5)
C17	0.0174 (5)	0.0234 (6)	0.0190 (5)	−0.0025 (4)	0.0083 (4)	0.0006 (4)
C18	0.0163 (5)	0.0238 (6)	0.0171 (5)	−0.0012 (4)	0.0078 (4)	0.0002 (4)
C19	0.0180 (5)	0.0252 (6)	0.0156 (5)	−0.0013 (4)	0.0081 (4)	−0.0006 (4)
C20	0.0186 (5)	0.0275 (6)	0.0225 (6)	−0.0038 (5)	0.0105 (4)	−0.0061 (5)

N1—C1	1.3608 (15)	C6—C7	1.3754 (19)
N1—C8	1.3815 (15)	C6—H6	0.9500
N1—C9	1.4527 (14)	C7—C8	1.3913 (17)
N2—C16	1.1459 (17)	C7—H7	0.9500
N3—C19	1.3650 (15)	C9—C10	1.5025 (16)
N3—C20	1.3812 (15)	C9—H9A	0.9900
N3—H3	0.8800	C9—H9B	0.9900
N4—C20	1.3576 (15)	C10—C11	1.3877 (17)
N4—C18	1.3926 (15)	C10—C15	1.3883 (16)
N4—H4	0.8800	C11—C12	1.3761 (17)
O1—C19	1.2246 (14)	C11—H11	0.9500
O2—C20	1.2178 (15)	C12—C13	1.3938 (17)
C1—C2	1.3772 (16)	C12—H12	0.9500
C1—H1	0.9500	C13—C14	1.3879 (17)
C2—C17	1.4348 (16)	C13—C16	1.4372 (17)
C2—C3	1.4416 (16)	C14—C15	1.3805 (17)
C3—C4	1.3967 (17)	C14—H14	0.9500
C3—C8	1.4064 (16)	C15—H15	0.9500
C4—C5	1.3759 (19)	C17—C18	1.3372 (17)
C4—H4A	0.9500	C17—H17	0.9500
C5—C6	1.398 (2)	C18—C19	1.4742 (15)
C5—H5	0.9500
C1—N1—C8	109.16 (9)	C10—C9—H9A	108.4
C1—N1—C9	124.09 (10)	N1—C9—H9B	108.4
C8—N1—C9	126.44 (10)	C10—C9—H9B	108.4
C19—N3—C20	111.43 (9)	H9A—C9—H9B	107.5
C19—N3—H3	124.3	C11—C10—C15	119.39 (11)
C20—N3—H3	124.3	C11—C10—C9	117.71 (10)
C20—N4—C18	111.14 (9)	C15—C10—C9	122.75 (10)
C20—N4—H4	124.4	C12—C11—C10	120.79 (11)
C18—N4—H4	124.4	C12—C11—H11	119.6
N1—C1—C2	110.27 (10)	C10—C11—H11	119.6
N1—C1—H1	124.9	C11—C12—C13	119.35 (11)
C2—C1—H1	124.9	C11—C12—H12	120.3
C1—C2—C17	128.96 (11)	C13—C12—H12	120.3
C1—C2—C3	105.97 (10)	C14—C13—C12	120.33 (11)
C17—C2—C3	125.00 (10)	C14—C13—C16	119.57 (11)
C4—C3—C8	119.03 (11)	C12—C13—C16	120.10 (11)
C4—C3—C2	133.85 (11)	C15—C14—C13	119.62 (11)
C8—C3—C2	107.12 (10)	C15—C14—H14	120.2
C5—C4—C3	118.39 (12)	C13—C14—H14	120.2
C5—C4—H4A	120.8	C14—C15—C10	120.43 (11)
C3—C4—H4A	120.8	C14—C15—H15	119.8
C4—C5—C6	121.63 (13)	C10—C15—H15	119.8
C4—C5—H5	119.2	N2—C16—C13	178.46 (14)
C6—C5—H5	119.2	C18—C17—C2	129.12 (11)
C7—C6—C5	121.37 (12)	C18—C17—H17	115.4
C7—C6—H6	119.3	C2—C17—H17	115.4
C5—C6—H6	119.3	C17—C18—N4	130.58 (10)
C6—C7—C8	116.92 (11)	C17—C18—C19	124.41 (10)
C6—C7—H7	121.5	N4—C18—C19	104.99 (9)
C8—C7—H7	121.5	O1—C19—N3	126.12 (10)
N1—C8—C7	129.86 (11)	O1—C19—C18	128.34 (10)
N1—C8—C3	107.48 (10)	N3—C19—C18	105.54 (9)
C7—C8—C3	122.66 (11)	O2—C20—N4	127.55 (11)
N1—C9—C10	115.55 (9)	O2—C20—N3	125.55 (11)
N1—C9—H9A	108.4	N4—C20—N3	106.90 (10)
C8—N1—C1—C2	−0.07 (13)	C15—C10—C11—C12	3.09 (18)
C9—N1—C1—C2	173.86 (10)	C9—C10—C11—C12	−172.46 (11)
N1—C1—C2—C17	−176.56 (11)	C10—C11—C12—C13	−0.67 (19)
N1—C1—C2—C3	0.49 (13)	C11—C12—C13—C14	−1.89 (19)
C1—C2—C3—C4	−179.90 (13)	C11—C12—C13—C16	177.54 (11)
C17—C2—C3—C4	−2.7 (2)	C12—C13—C14—C15	1.98 (18)
C1—C2—C3—C8	−0.72 (12)	C16—C13—C14—C15	−177.45 (11)
C17—C2—C3—C8	176.48 (10)	C13—C14—C15—C10	0.48 (17)
C8—C3—C4—C5	0.24 (18)	C11—C10—C15—C14	−2.99 (17)
C2—C3—C4—C5	179.34 (12)	C9—C10—C15—C14	172.32 (11)
C3—C4—C5—C6	−0.4 (2)	C1—C2—C17—C18	−4.0 (2)
C4—C5—C6—C7	0.0 (2)	C3—C2—C17—C18	179.49 (11)
C5—C6—C7—C8	0.6 (2)	C2—C17—C18—N4	−0.3 (2)
C1—N1—C8—C7	179.20 (12)	C2—C17—C18—C19	−178.46 (11)
C9—N1—C8—C7	5.45 (19)	C20—N4—C18—C17	−178.60 (12)
C1—N1—C8—C3	−0.40 (12)	C20—N4—C18—C19	−0.22 (12)
C9—N1—C8—C3	−174.15 (10)	C20—N3—C19—O1	179.92 (11)
C6—C7—C8—N1	179.66 (12)	C20—N3—C19—C18	0.11 (12)
C6—C7—C8—C3	−0.79 (18)	C17—C18—C19—O1	−1.22 (19)
C4—C3—C8—N1	−179.99 (10)	N4—C18—C19—O1	−179.74 (11)
C2—C3—C8—N1	0.69 (12)	C17—C18—C19—N3	178.58 (10)
C4—C3—C8—C7	0.38 (17)	N4—C18—C19—N3	0.06 (11)
C2—C3—C8—C7	−178.95 (11)	C18—N4—C20—O2	179.95 (12)
C1—N1—C9—C10	103.89 (13)	C18—N4—C20—N3	0.28 (13)
C8—N1—C9—C10	−83.24 (14)	C19—N3—C20—O2	−179.91 (11)
N1—C9—C10—C11	−157.33 (11)	C19—N3—C20—N4	−0.24 (13)
N1—C9—C10—C15	27.28 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.88	1.95	2.8237 (12)	173
N4—H4···O2ii	0.88	2.07	2.8740 (13)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.88	1.95	2.8237 (12)	173
N4—H4⋯O2ii	0.88	2.07	2.8740 (13)	151

Symmetry codes: (i) ; (ii) .