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In the title compound, C25H17N5, the two bulky substituents, viz. 4-cyano­phenyl and 2-phenyl­indolizin-3-yl, are situated on the same side of the C=C double bond, resulting in an E configuration. The crystal packing is stabilized by weak non-classical inter­molecular C—H...N hydrogen bonds and slipped π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035672/dn2219sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035672/dn2219Isup2.hkl
Contains datablock I

CCDC reference: 657846

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.122
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C20 - C25 ... 1.44 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C18 .. C18 .. 3.19 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H24 .. N4 .. 2.67 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Indolizines and triazoles are important heterocyclic nitrogen compounds which display a wide range of biological activity. The synthetic indolozine (Gundersen et al., 2007) and triazole (Itoh et al., 2007) derivatives, have been used as antitumor (Mehta et al., 1995), anti–inflammatory (Malonne et al., 1998), antiviral agent (Ebeid et al., 1997) and also as antihypertensive (Clive et al., 1999). We report here the structure and stereochemistry of the title compound (I), which resulted from the condensation of 3-thioformylindolizine with 4-[(1H-1,2,4-triazol-1- yl)methyl] benzonitrile containing indolizine and triazole ring.

Compound (I) (Fig.1) assumes an E-conformation. There is a twist in the molecule as seen in the C1—C15—C16—C17 and the C15—C1—C2—C9 torsion angles of -9.8 (3)° and -3.0 (3)°, respectively. This is also reflected in the dihedral angles of 68.347 (76)° and 43.322 (53)° formed between C23—C24/N2—N3 and C17—C22 and C9—C14 and C1—C8/N1 respectively.

The two bulky substituted indolizinyl and 4-cyanophenyl rings are on the same side. Such conformation results from the occurrence of weak intramolecular π···π interactions (Table 2, Fig.1). There are also intermolecular slippest π···π stacking and weak C—H···N hydrogen-bonding resulting in the formation of pseudo-dimers across inversion centers (Fig.2, Tables 1 and 2) which are further interconnected to form a three dimensional network.

Related literature top

For related literature, see: Clive et al. (1999); Ebeid et al. (1997); Gundersen et al. (2007); Itoh et al. (2007); Malonne et al. (1998); Mehta & Parrick (1995).

Experimental top

A solution of 4-[(1H-1,2,4-triazol-1-yl)methyl]benzonitrile(0.24 g, 1.30 mmol), sodium hydroxide (0.05 g, 1.25 mmol) and 2-phenyl-3-thioformylindolizine(0.237 g, 1.00 mmol) in anhydrous dimethylformamide(15 ml) was stirred at ~343- 358 K, until all the thial had disappeared (monitored by thin-layer chromatography). The resulting mixture was chromatographed on a column of silica gel with petroleum ether and ethyl acetate as eluents for stepwise elution. Evaporation of the eluents gave the title compound as yellow solid. Single crystals of (I) suitable for x-ray crystallographic analysis were obtained by recrystallization from a mixture of petroleum ether and ethyl acetate.

Refinement top

All H atoms were fixed geometrically and treated as riding on their parent atoms with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

Indolizines and triazoles are important heterocyclic nitrogen compounds which display a wide range of biological activity. The synthetic indolozine (Gundersen et al., 2007) and triazole (Itoh et al., 2007) derivatives, have been used as antitumor (Mehta et al., 1995), anti–inflammatory (Malonne et al., 1998), antiviral agent (Ebeid et al., 1997) and also as antihypertensive (Clive et al., 1999). We report here the structure and stereochemistry of the title compound (I), which resulted from the condensation of 3-thioformylindolizine with 4-[(1H-1,2,4-triazol-1- yl)methyl] benzonitrile containing indolizine and triazole ring.

Compound (I) (Fig.1) assumes an E-conformation. There is a twist in the molecule as seen in the C1—C15—C16—C17 and the C15—C1—C2—C9 torsion angles of -9.8 (3)° and -3.0 (3)°, respectively. This is also reflected in the dihedral angles of 68.347 (76)° and 43.322 (53)° formed between C23—C24/N2—N3 and C17—C22 and C9—C14 and C1—C8/N1 respectively.

The two bulky substituted indolizinyl and 4-cyanophenyl rings are on the same side. Such conformation results from the occurrence of weak intramolecular π···π interactions (Table 2, Fig.1). There are also intermolecular slippest π···π stacking and weak C—H···N hydrogen-bonding resulting in the formation of pseudo-dimers across inversion centers (Fig.2, Tables 1 and 2) which are further interconnected to form a three dimensional network.

For related literature, see: Clive et al. (1999); Ebeid et al. (1997); Gundersen et al. (2007); Itoh et al. (2007); Malonne et al. (1998); Mehta & Parrick (1995).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level and H atoms are represented by spheres of arbitrary radii. Dashed line represent the intramolecular π-π stacking.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of intermolecular π···π (dashed lines) interaction. H atoms have been omitted for clarity. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) -x, 1 - y, 1 - z; (iii) -x, 1 - y, 2 - z; (iv) x, y, z - 1].
(E)-4-[2-(2-Phenylindolizin-3-yl)-1-(1,2,4-triazol-1-yl)vinyl]benzonitrile top
Crystal data top
C25H17N5Z = 2
Mr = 387.44F(000) = 404
Triclinic, P1Dx = 1.274 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.947 (5) ÅCell parameters from 1975 reflections
b = 9.996 (5) Åθ = 2.5–27.1°
c = 10.833 (5) ŵ = 0.08 mm1
α = 83.381 (5)°T = 298 K
β = 74.695 (6)°Prism, yellow
γ = 76.924 (6)°0.58 × 0.50 × 0.37 mm
V = 1010.2 (9) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3492 independent reflections
Radiation source: fine-focus sealed tube2413 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 611
Tmin = 0.956, Tmax = 0.972k = 1011
5230 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.1782P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3492 reflectionsΔρmax = 0.19 e Å3
272 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (4)
Crystal data top
C25H17N5γ = 76.924 (6)°
Mr = 387.44V = 1010.2 (9) Å3
Triclinic, P1Z = 2
a = 9.947 (5) ÅMo Kα radiation
b = 9.996 (5) ŵ = 0.08 mm1
c = 10.833 (5) ÅT = 298 K
α = 83.381 (5)°0.58 × 0.50 × 0.37 mm
β = 74.695 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3492 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2413 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.972Rint = 0.032
5230 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.02Δρmax = 0.19 e Å3
3492 reflectionsΔρmin = 0.19 e Å3
272 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 > σ(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
xyzUiso*/Ueq
N10.38641 (16)0.43743 (16)0.64233 (14)0.0410 (4)
N20.03197 (16)0.79181 (15)0.73271 (14)0.0399 (4)
N30.16952 (17)0.78722 (18)0.79478 (16)0.0508 (5)
N40.1620 (2)0.9431 (2)0.62648 (18)0.0661 (6)
N50.0589 (3)0.6483 (3)1.4102 (2)0.0964 (8)
C10.3291 (2)0.56631 (19)0.68966 (17)0.0400 (5)
C20.4254 (2)0.5964 (2)0.75032 (17)0.0423 (5)
C30.5397 (2)0.4840 (2)0.74142 (19)0.0499 (5)
H30.61830.47720.77460.060*
C40.5164 (2)0.3841 (2)0.67480 (18)0.0463 (5)
C50.5885 (2)0.2513 (2)0.63865 (19)0.0549 (6)
H50.67660.21480.65610.066*
C60.5305 (3)0.1764 (2)0.5786 (2)0.0612 (6)
H60.57740.08750.55710.073*
C70.3985 (3)0.2329 (2)0.5484 (2)0.0604 (6)
H70.35980.18140.50590.072*
C80.3282 (2)0.3609 (2)0.58079 (18)0.0504 (5)
H80.24080.39710.56160.060*
C90.4068 (2)0.7238 (2)0.81463 (18)0.0438 (5)
C100.4369 (2)0.7183 (2)0.9333 (2)0.0583 (6)
H100.47400.63390.97000.070*
C110.4124 (3)0.8362 (3)0.9976 (2)0.0713 (7)
H110.43230.83041.07740.086*
C120.3592 (3)0.9612 (3)0.9449 (2)0.0681 (7)
H120.34081.04010.98950.082*
C130.3329 (2)0.9699 (2)0.8258 (2)0.0580 (6)
H130.30011.05530.78830.070*
C140.3552 (2)0.8519 (2)0.76121 (19)0.0486 (5)
H140.33530.85860.68120.058*
C150.1904 (2)0.64008 (19)0.67592 (18)0.0424 (5)
H150.17240.64500.59540.051*
C160.08603 (19)0.70170 (18)0.76966 (17)0.0370 (4)
C170.08146 (18)0.69058 (19)0.90751 (17)0.0369 (4)
C180.13747 (19)0.5670 (2)0.96614 (18)0.0417 (5)
H180.17890.49090.91720.050*
C190.1329 (2)0.5549 (2)1.09464 (19)0.0468 (5)
H190.17050.47131.13220.056*
C200.0721 (2)0.6680 (2)1.16816 (18)0.0486 (5)
C210.0155 (2)0.7910 (2)1.11187 (19)0.0546 (6)
H210.02540.86691.16110.066*
C220.0191 (2)0.8026 (2)0.98321 (19)0.0482 (5)
H220.02060.88590.94650.058*
C230.2408 (2)0.8792 (2)0.7270 (2)0.0556 (6)
H230.33980.89930.74680.067*
C240.0326 (2)0.8845 (2)0.6342 (2)0.0561 (6)
H240.04920.90520.57760.067*
C250.0644 (2)0.6565 (3)1.3034 (2)0.0658 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0360 (9)0.0447 (10)0.0383 (9)0.0013 (7)0.0068 (7)0.0048 (7)
N20.0330 (9)0.0432 (9)0.0408 (9)0.0017 (7)0.0115 (7)0.0018 (7)
N30.0307 (9)0.0608 (11)0.0566 (10)0.0058 (8)0.0096 (8)0.0046 (8)
N40.0479 (12)0.0727 (13)0.0618 (12)0.0113 (10)0.0141 (9)0.0143 (10)
N50.0971 (19)0.151 (2)0.0522 (13)0.0378 (17)0.0296 (13)0.0002 (14)
C10.0368 (11)0.0423 (11)0.0380 (10)0.0016 (9)0.0093 (8)0.0038 (8)
C20.0350 (11)0.0489 (12)0.0428 (11)0.0081 (9)0.0110 (9)0.0000 (9)
C30.0347 (11)0.0577 (13)0.0570 (13)0.0046 (10)0.0177 (10)0.0032 (10)
C40.0359 (11)0.0483 (12)0.0469 (11)0.0012 (9)0.0072 (9)0.0027 (9)
C50.0447 (13)0.0532 (13)0.0533 (13)0.0061 (11)0.0049 (10)0.0028 (10)
C60.0712 (17)0.0484 (13)0.0506 (13)0.0065 (12)0.0067 (12)0.0057 (10)
C70.0732 (17)0.0543 (14)0.0503 (13)0.0062 (12)0.0112 (11)0.0128 (10)
C80.0496 (13)0.0571 (13)0.0438 (11)0.0064 (11)0.0126 (10)0.0069 (10)
C90.0319 (11)0.0544 (13)0.0459 (11)0.0135 (9)0.0075 (9)0.0013 (9)
C100.0631 (15)0.0640 (15)0.0586 (14)0.0280 (12)0.0241 (11)0.0048 (11)
C110.0860 (19)0.087 (2)0.0572 (14)0.0423 (16)0.0224 (13)0.0077 (14)
C120.0664 (16)0.0744 (18)0.0677 (16)0.0329 (14)0.0001 (13)0.0241 (13)
C130.0459 (13)0.0517 (13)0.0718 (16)0.0155 (11)0.0001 (11)0.0074 (11)
C140.0384 (12)0.0563 (14)0.0497 (12)0.0110 (10)0.0071 (9)0.0036 (10)
C150.0399 (11)0.0480 (12)0.0408 (11)0.0029 (9)0.0168 (9)0.0050 (9)
C160.0321 (10)0.0386 (10)0.0419 (10)0.0060 (8)0.0135 (8)0.0004 (8)
C170.0278 (10)0.0433 (11)0.0406 (10)0.0096 (8)0.0097 (8)0.0010 (8)
C180.0357 (11)0.0440 (11)0.0478 (11)0.0118 (9)0.0135 (9)0.0021 (9)
C190.0415 (12)0.0531 (13)0.0519 (12)0.0187 (10)0.0212 (10)0.0134 (10)
C200.0408 (12)0.0694 (15)0.0412 (11)0.0210 (11)0.0140 (9)0.0029 (10)
C210.0535 (14)0.0615 (14)0.0487 (12)0.0068 (11)0.0120 (10)0.0134 (10)
C220.0476 (13)0.0459 (12)0.0496 (12)0.0021 (10)0.0162 (10)0.0021 (9)
C230.0345 (12)0.0652 (14)0.0609 (14)0.0055 (11)0.0160 (10)0.0010 (11)
C240.0452 (13)0.0592 (13)0.0532 (13)0.0027 (11)0.0114 (10)0.0120 (11)
C250.0553 (15)0.098 (2)0.0529 (14)0.0252 (13)0.0229 (12)0.0029 (13)
Geometric parameters (Å, º) top
N1—C81.374 (3)C10—C111.380 (3)
N1—C11.383 (2)C10—H100.9300
N1—C41.402 (2)C11—C121.365 (3)
N2—C241.330 (2)C11—H110.9300
N2—N31.364 (2)C12—C131.371 (3)
N2—C161.427 (2)C12—H120.9300
N3—C231.308 (2)C13—C141.386 (3)
N4—C241.308 (3)C13—H130.9300
N4—C231.351 (3)C14—H140.9300
N5—C251.138 (3)C15—C161.337 (3)
C1—C21.395 (3)C15—H150.9300
C1—C151.446 (3)C16—C171.474 (3)
C2—C31.397 (3)C17—C181.391 (2)
C2—C91.474 (3)C17—C221.393 (3)
C3—C41.390 (3)C18—C191.373 (3)
C3—H30.9300C18—H180.9300
C4—C51.403 (3)C19—C201.386 (3)
C5—C61.350 (3)C19—H190.9300
C5—H50.9300C20—C211.377 (3)
C6—C71.413 (3)C20—C251.439 (3)
C6—H60.9300C21—C221.377 (3)
C7—C81.348 (3)C21—H210.9300
C7—H70.9300C22—H220.9300
C8—H80.9300C23—H230.9300
C9—C101.387 (3)C24—H240.9300
C9—C141.388 (3)
C8—N1—C1128.76 (17)C11—C12—C13119.6 (2)
C8—N1—C4121.32 (17)C11—C12—H12120.2
C1—N1—C4109.75 (16)C13—C12—H12120.2
C24—N2—N3108.51 (16)C12—C13—C14120.3 (2)
C24—N2—C16129.20 (17)C12—C13—H13119.9
N3—N2—C16122.18 (15)C14—C13—H13119.9
C23—N3—N2102.02 (16)C13—C14—C9120.7 (2)
C24—N4—C23101.48 (18)C13—C14—H14119.7
N1—C1—C2107.01 (16)C9—C14—H14119.7
N1—C1—C15120.65 (17)C16—C15—C1125.28 (17)
C2—C1—C15132.28 (18)C16—C15—H15117.4
C1—C2—C3108.12 (18)C1—C15—H15117.4
C1—C2—C9125.41 (17)C15—C16—N2116.93 (16)
C3—C2—C9126.46 (18)C15—C16—C17127.03 (17)
C4—C3—C2108.75 (17)N2—C16—C17116.00 (15)
C4—C3—H3125.6C18—C17—C22118.07 (17)
C2—C3—H3125.6C18—C17—C16120.82 (17)
C3—C4—N1106.36 (17)C22—C17—C16121.10 (16)
C3—C4—C5135.6 (2)C19—C18—C17121.42 (19)
N1—C4—C5118.1 (2)C19—C18—H18119.3
C6—C5—C4120.3 (2)C17—C18—H18119.3
C6—C5—H5119.8C18—C19—C20119.70 (18)
C4—C5—H5119.8C18—C19—H19120.2
C5—C6—C7120.1 (2)C20—C19—H19120.2
C5—C6—H6120.0C21—C20—C19119.68 (18)
C7—C6—H6120.0C21—C20—C25119.9 (2)
C8—C7—C6120.6 (2)C19—C20—C25120.4 (2)
C8—C7—H7119.7C20—C21—C22120.5 (2)
C6—C7—H7119.7C20—C21—H21119.7
C7—C8—N1119.5 (2)C22—C21—H21119.7
C7—C8—H8120.2C21—C22—C17120.59 (19)
N1—C8—H8120.2C21—C22—H22119.7
C10—C9—C14118.0 (2)C17—C22—H22119.7
C10—C9—C2120.40 (18)N3—C23—N4115.99 (19)
C14—C9—C2121.62 (18)N3—C23—H23122.0
C11—C10—C9120.9 (2)N4—C23—H23122.0
C11—C10—H10119.6N4—C24—N2112.00 (19)
C9—C10—H10119.6N4—C24—H24124.0
C12—C11—C10120.5 (2)N2—C24—H24124.0
C12—C11—H11119.7N5—C25—C20179.4 (3)
C10—C11—H11119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···N5i0.932.543.448 (3)165
C19—H19···N3ii0.932.623.462 (3)152
C24—H24···N4iii0.932.673.492 (3)148
Symmetry codes: (i) x, y, z1; (ii) x, y+1, z+2; (iii) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC25H17N5
Mr387.44
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.947 (5), 9.996 (5), 10.833 (5)
α, β, γ (°)83.381 (5), 74.695 (6), 76.924 (6)
V3)1010.2 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.58 × 0.50 × 0.37
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.956, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
5230, 3492, 2413
Rint0.032
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.122, 1.02
No. of reflections3492
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···N5i0.932.543.448 (3)164.8
C19—H19···N3ii0.932.623.462 (3)151.7
C24—H24···N4iii0.932.673.492 (3)147.6
Symmetry codes: (i) x, y, z1; (ii) x, y+1, z+2; (iii) x, y+2, z+1.
Intra- and intermolecular ππ interactions (Å) top
CentroidsCentroid-to-centroidPlane-to-planeSlippage
Cg1···Cg2i3.724 (2)3.6220.867
Cg3···Cg43.724 (2)3.5361.168
Cg1, Cg2, Cg3 and Cg4 are the centroids of the N1/C1–C4, N1/C4–C8, C9–C14 and C17–C22 rings, respectively. [Symmetry code: (i) 1-x, 1-y, 1-z]
 

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