(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemeth­yl)-1H-indol-1-ylmeth­yl]benzonitrile

Penthala, N.R.; Reddy, T.R.Y.; Parkin, S.; Crooks, P.A.

doi:10.1107/S1600536808032601

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2122

doi:10.1107/S1600536808032601

Open

access

(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemethyl)-1H-indol-1-ylmethyl]benzonitrile

Narsimha Reddy Penthala,^a Thirupathi Reddy Yerram Reddy,^a Sean Parkin ^b and Peter A. Crooks ^a ^*

^aDepartment of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA
^*Correspondence e-mail: pcrooks@uky.edu

(Received 19 September 2008; accepted 9 October 2008; online 18 October 2008)

In the title compound, C₂₀H₁₄N₄O₂, molecules are linked into chains by N—H⋯O hydrogen bonds, but the cyano group does not participate in the supramolecular 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_r = 342.35
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.088
S = 1.04
3025 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) -x+1, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032601/fj2156sup1.cif

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

checkCIF report

Comment top

As part of a continuing search for biologically active molecules containing indole ring systems (Sonar et al., 2007), we have now prepared the title compound by the reaction of 4-(3-formyl-1H-indol-1-ylmethyl)benzonitrile with imidazolidine-2,4-dione in the presence of ammonium acetate in acetic acid at 393 K. The compound was crystallized from a mixture of methanol and ethylacetate. The molecular structure and the atom-numbering scheme are shown in Fig.1. The indole ring is planar with bond distances and angles comparable with those previously reported for other indole derivatives (Mason et al., 2003; Zarza, et al., 1988). The X-ray studies revealed that the obtained compound is the Z isomer. The C18—C19 bond is in a trans position with respect to the C2—C17 bond. The olefinic bond (C17=C18) has a planar atomic arrangement, since the r.m.s. deviation from the mean plane passing through atoms C2, C17, C18, N4 is 0.0009 (5) Å. The maximum deviation from plane for imidazoline ring is 0.0087 Å. Deviations from ideal geometry are observed in the bond angles around atoms C2, C17 and C18. The C17=C18—C19 bond angle is close to the standard planar triangular value of 120°, whereas the C1=C2—C17, C18—C17=C2 and C17=C18—N4 bond angles are more distorted due to the strain induced by the C17=C18—C1=O1 conjugated double bond linkage. These bond angle deformations, which require little energy, are needed to release the intramolecular interactions between non-bonded atoms. The imidazolidine ring, which makes a dihedral angle of 2.48 (5)° with the adjacent aromatic ring presents very small distortions around atoms N4, C20, N3 and C19.

Significant intermolecular hydrogen-bonding interactions are found between N(3)—H(3)···O(1) and N(4)—H(4)···O(2). Molecules are linked into chains by a series of N—H···O hydrogen bonds.

Related literature top

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 top

A mixture of 4-(3-formyl-indol-1-ylmethyl)benzonitrile (0.5 g, 1.92 mmol), imidazolidine-2,4-dione (0.23 g, 2.30 mmol) and ammonium acetate (0.15 g, 1.94 mmol) was stirred in acetic acid (5 ml) at 393 K for 10 hrs. The reaction mixture was cooled to room temperature and the yellow solid that separated was collected by filtration, washed with cold water and dried to afford the the crude product. Crystallization from methanol and ethyl acetate (1:1) gave a yellow crystalline product of (Z)-4-((3-((2,5- dioxoimidazolidin-4-ylidene)methyl)-1H-indol-1-yl)methyl) benzonitrile that was suitable for X-ray analysis. ¹H NMR (DMSO d₆): δ 5.56 (s, 2H), 6.7 (s, 1H), 7.13–7.23 (m, 2H), 7.44–7.53 (m, 3H), 7.79–7.83 (m, 3H), 8.30 (s, 1H), 10.15 (bs, 1H), 11.07 (bs, 1H); ¹³C NMR (DMSO d₆): δ 101.46, 109.25, 111.06, 111.22, 119.21, 119.29, 121.34, 123.42, 124.95, 128.10, 128.70, 130.63, 133.26, 136.25, 143.71, 155.94, 165.87.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); 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: SHELX97 (Sheldrick, 2008) and local procedures.

Figures top

Fig. 1. A view of the molecule with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemethyl)-1H-indol- 1-ylmethyl]benzonitrile top

Crystal data top

C₂₀H₁₄N₄O₂	F(000) = 1424
M_r = 342.35	D_x = 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

Data collection top

Bruker X8 Proteum diffractometer	3025 independent reflections
Radiation source: fine-focus rotating anode	2849 reflections with I > 2σ(I)
Graded multilayer optics monochromator	R_int = 0.039
Detector resolution: 18 pixels mm^-1	θ_max = 68.8°, θ_min = 3.9°
ϕ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2006)	k = −9→9
T_min = 0.806, T_max = 0.957	l = −28→29
23493 measured reflections

Refinement top

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(F_o²) + (0.043P)² + 2.7005P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3025 reflections	Δρ_max = 0.24 e Å⁻³
236 parameters	Δρ_min = −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)

Crystal data top

C₂₀H₁₄N₄O₂	V = 3289.0 (5) Å³
M_r = 342.35	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 18.8495 (16) Å	µ = 0.76 mm⁻¹
b = 7.6812 (7) Å	T = 90 K
c = 24.322 (2) Å	0.15 × 0.08 × 0.06 mm
β = 110.939 (3)°

Data collection top

Bruker X8 Proteum diffractometer	3025 independent reflections
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2006)	2849 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.957	R_int = 0.039
23493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
3025 reflections	Δρ_min = −0.30 e Å⁻³
236 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y+1/2, −z+1; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄N₄O₂
M_r	342.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	90
a, b, c (Å)	18.8495 (16), 7.6812 (7), 24.322 (2)
β (°)	110.939 (3)
V (Å³)	3289.0 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.15 × 0.08 × 0.06

Data collection
Diffractometer	Bruker X8 Proteum diffractometer
Absorption correction	Multi-scan (SADABS in APEX2; Bruker, 2006)
T_min, T_max	0.806, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	23493, 3025, 2849
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 1.04
No. of reflections	3025
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: APEX2 (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELX97 (Sheldrick, 2008) and local procedures.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88	1.95	2.8237 (12)	172.9
N4—H4···O2ⁱⁱ	0.88	2.07	2.8740 (13)	151.4

Symmetry codes: (i) −x+3/2, −y+1/2, −z+1; (ii) −x+1, −y, −z+1.

Acknowledgements

This investigation was supported by NIH/National Cancer Institute grant PO1 CA104457 (to PAC) and by NSF MRI grant CHE 0319176 (to SP).

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Mason, M. R., Barnard, T. S., Segla, M. F., Xie, B. & Kirschbaum, K. (2003). J. Chem. Crystallogr. 33, 531–540. Web of Science CSD CrossRef CAS Google Scholar
Sekhar, K. R., Crooks, P. A., Sonar, V. N., Friedman, D. B., Chan, J. Y., Meredith, M. J., Stames, J. H., Kelton, K. R., Summar, S. R., Sasi, S. & Freeman, M. L. (2003). Cancer Res. 63, 5636–5645. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sonar, V. N., Reddy, Y. T., Sekhar, K. R., Sowmya, S., Freeman, M. L. & Crooks, P. A. (2007). Bioorg. Med. Chem. Lett. 17, 6821–6824. Web of Science CrossRef PubMed CAS Google Scholar
Zarza, P. M., Gill, P., Díaz González, M. C., Martin Reyes, M. G., Arrieta, J. M., Nastopoulos, V., Germain, G. & Debaerdemaeker, T. (1988). Acta Cryst. C44, 678–681. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2122

doi:10.1107/S1600536808032601

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemeth­yl)-1H-indol-1-ylmeth­yl]benzo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-4-[3-(2,5-Dioxoimidazolidin-4-ylidenemethyl)-1H-indol-1-ylmethyl]benzonitrile