Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035672/dn2219sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035672/dn2219Isup2.hkl |
CCDC reference: 657846
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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).
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.
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).
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).
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.
C25H17N5 | Z = 2 |
Mr = 387.44 | F(000) = 404 |
Triclinic, P1 | Dx = 1.274 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.947 (5) Å | Cell parameters from 1975 reflections |
b = 9.996 (5) Å | θ = 2.5–27.1° |
c = 10.833 (5) Å | µ = 0.08 mm−1 |
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 |
Bruker SMART CCD area-detector diffractometer | 3492 independent reflections |
Radiation source: fine-focus sealed tube | 2413 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −6→11 |
Tmin = 0.956, Tmax = 0.972 | k = −10→11 |
5230 measured reflections | l = −12→12 |
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)] = 0.044 | H-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 reflections | Δρmax = 0.19 e Å−3 |
272 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.036 (4) |
C25H17N5 | γ = 76.924 (6)° |
Mr = 387.44 | V = 1010.2 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.947 (5) Å | Mo Kα radiation |
b = 9.996 (5) Å | µ = 0.08 mm−1 |
c = 10.833 (5) Å | T = 298 K |
α = 83.381 (5)° | 0.58 × 0.50 × 0.37 mm |
β = 74.695 (6)° |
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 = 0.972 | Rint = 0.032 |
5230 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.19 e Å−3 |
3492 reflections | Δρmin = −0.19 e Å−3 |
272 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.38641 (16) | 0.43743 (16) | 0.64233 (14) | 0.0410 (4) | |
N2 | −0.03197 (16) | 0.79181 (15) | 0.73271 (14) | 0.0399 (4) | |
N3 | −0.16952 (17) | 0.78722 (18) | 0.79478 (16) | 0.0508 (5) | |
N4 | −0.1620 (2) | 0.9431 (2) | 0.62648 (18) | 0.0661 (6) | |
N5 | 0.0589 (3) | 0.6483 (3) | 1.4102 (2) | 0.0964 (8) | |
C1 | 0.3291 (2) | 0.56631 (19) | 0.68966 (17) | 0.0400 (5) | |
C2 | 0.4254 (2) | 0.5964 (2) | 0.75032 (17) | 0.0423 (5) | |
C3 | 0.5397 (2) | 0.4840 (2) | 0.74142 (19) | 0.0499 (5) | |
H3 | 0.6183 | 0.4772 | 0.7746 | 0.060* | |
C4 | 0.5164 (2) | 0.3841 (2) | 0.67480 (18) | 0.0463 (5) | |
C5 | 0.5885 (2) | 0.2513 (2) | 0.63865 (19) | 0.0549 (6) | |
H5 | 0.6766 | 0.2148 | 0.6561 | 0.066* | |
C6 | 0.5305 (3) | 0.1764 (2) | 0.5786 (2) | 0.0612 (6) | |
H6 | 0.5774 | 0.0875 | 0.5571 | 0.073* | |
C7 | 0.3985 (3) | 0.2329 (2) | 0.5484 (2) | 0.0604 (6) | |
H7 | 0.3598 | 0.1814 | 0.5059 | 0.072* | |
C8 | 0.3282 (2) | 0.3609 (2) | 0.58079 (18) | 0.0504 (5) | |
H8 | 0.2408 | 0.3971 | 0.5616 | 0.060* | |
C9 | 0.4068 (2) | 0.7238 (2) | 0.81463 (18) | 0.0438 (5) | |
C10 | 0.4369 (2) | 0.7183 (2) | 0.9333 (2) | 0.0583 (6) | |
H10 | 0.4740 | 0.6339 | 0.9700 | 0.070* | |
C11 | 0.4124 (3) | 0.8362 (3) | 0.9976 (2) | 0.0713 (7) | |
H11 | 0.4323 | 0.8304 | 1.0774 | 0.086* | |
C12 | 0.3592 (3) | 0.9612 (3) | 0.9449 (2) | 0.0681 (7) | |
H12 | 0.3408 | 1.0401 | 0.9895 | 0.082* | |
C13 | 0.3329 (2) | 0.9699 (2) | 0.8258 (2) | 0.0580 (6) | |
H13 | 0.3001 | 1.0553 | 0.7883 | 0.070* | |
C14 | 0.3552 (2) | 0.8519 (2) | 0.76121 (19) | 0.0486 (5) | |
H14 | 0.3353 | 0.8586 | 0.6812 | 0.058* | |
C15 | 0.1904 (2) | 0.64008 (19) | 0.67592 (18) | 0.0424 (5) | |
H15 | 0.1724 | 0.6450 | 0.5954 | 0.051* | |
C16 | 0.08603 (19) | 0.70170 (18) | 0.76966 (17) | 0.0370 (4) | |
C17 | 0.08146 (18) | 0.69058 (19) | 0.90751 (17) | 0.0369 (4) | |
C18 | 0.13747 (19) | 0.5670 (2) | 0.96614 (18) | 0.0417 (5) | |
H18 | 0.1789 | 0.4909 | 0.9172 | 0.050* | |
C19 | 0.1329 (2) | 0.5549 (2) | 1.09464 (19) | 0.0468 (5) | |
H19 | 0.1705 | 0.4713 | 1.1322 | 0.056* | |
C20 | 0.0721 (2) | 0.6680 (2) | 1.16816 (18) | 0.0486 (5) | |
C21 | 0.0155 (2) | 0.7910 (2) | 1.11187 (19) | 0.0546 (6) | |
H21 | −0.0254 | 0.8669 | 1.1611 | 0.066* | |
C22 | 0.0191 (2) | 0.8026 (2) | 0.98321 (19) | 0.0482 (5) | |
H22 | −0.0206 | 0.8859 | 0.9465 | 0.058* | |
C23 | −0.2408 (2) | 0.8792 (2) | 0.7270 (2) | 0.0556 (6) | |
H23 | −0.3398 | 0.8993 | 0.7468 | 0.067* | |
C24 | −0.0326 (2) | 0.8845 (2) | 0.6342 (2) | 0.0561 (6) | |
H24 | 0.0492 | 0.9052 | 0.5776 | 0.067* | |
C25 | 0.0644 (2) | 0.6565 (3) | 1.3034 (2) | 0.0658 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0360 (9) | 0.0447 (10) | 0.0383 (9) | −0.0013 (7) | −0.0068 (7) | −0.0048 (7) |
N2 | 0.0330 (9) | 0.0432 (9) | 0.0408 (9) | −0.0017 (7) | −0.0115 (7) | 0.0018 (7) |
N3 | 0.0307 (9) | 0.0608 (11) | 0.0566 (10) | −0.0058 (8) | −0.0096 (8) | 0.0046 (8) |
N4 | 0.0479 (12) | 0.0727 (13) | 0.0618 (12) | 0.0113 (10) | −0.0141 (9) | 0.0143 (10) |
N5 | 0.0971 (19) | 0.151 (2) | 0.0522 (13) | −0.0378 (17) | −0.0296 (13) | 0.0002 (14) |
C1 | 0.0368 (11) | 0.0423 (11) | 0.0380 (10) | −0.0016 (9) | −0.0093 (8) | −0.0038 (8) |
C2 | 0.0350 (11) | 0.0489 (12) | 0.0428 (11) | −0.0081 (9) | −0.0110 (9) | 0.0000 (9) |
C3 | 0.0347 (11) | 0.0577 (13) | 0.0570 (13) | −0.0046 (10) | −0.0177 (10) | 0.0032 (10) |
C4 | 0.0359 (11) | 0.0483 (12) | 0.0469 (11) | 0.0012 (9) | −0.0072 (9) | 0.0027 (9) |
C5 | 0.0447 (13) | 0.0532 (13) | 0.0533 (13) | 0.0061 (11) | −0.0049 (10) | 0.0028 (10) |
C6 | 0.0712 (17) | 0.0484 (13) | 0.0506 (13) | 0.0065 (12) | −0.0067 (12) | −0.0057 (10) |
C7 | 0.0732 (17) | 0.0543 (14) | 0.0503 (13) | −0.0062 (12) | −0.0112 (11) | −0.0128 (10) |
C8 | 0.0496 (13) | 0.0571 (13) | 0.0438 (11) | −0.0064 (11) | −0.0126 (10) | −0.0069 (10) |
C9 | 0.0319 (11) | 0.0544 (13) | 0.0459 (11) | −0.0135 (9) | −0.0075 (9) | −0.0013 (9) |
C10 | 0.0631 (15) | 0.0640 (15) | 0.0586 (14) | −0.0280 (12) | −0.0241 (11) | 0.0048 (11) |
C11 | 0.0860 (19) | 0.087 (2) | 0.0572 (14) | −0.0423 (16) | −0.0224 (13) | −0.0077 (14) |
C12 | 0.0664 (16) | 0.0744 (18) | 0.0677 (16) | −0.0329 (14) | 0.0001 (13) | −0.0241 (13) |
C13 | 0.0459 (13) | 0.0517 (13) | 0.0718 (16) | −0.0155 (11) | −0.0001 (11) | −0.0074 (11) |
C14 | 0.0384 (12) | 0.0563 (14) | 0.0497 (12) | −0.0110 (10) | −0.0071 (9) | −0.0036 (10) |
C15 | 0.0399 (11) | 0.0480 (12) | 0.0408 (11) | −0.0029 (9) | −0.0168 (9) | −0.0050 (9) |
C16 | 0.0321 (10) | 0.0386 (10) | 0.0419 (10) | −0.0060 (8) | −0.0135 (8) | −0.0004 (8) |
C17 | 0.0278 (10) | 0.0433 (11) | 0.0406 (10) | −0.0096 (8) | −0.0097 (8) | 0.0010 (8) |
C18 | 0.0357 (11) | 0.0440 (11) | 0.0478 (11) | −0.0118 (9) | −0.0135 (9) | 0.0021 (9) |
C19 | 0.0415 (12) | 0.0531 (13) | 0.0519 (12) | −0.0187 (10) | −0.0212 (10) | 0.0134 (10) |
C20 | 0.0408 (12) | 0.0694 (15) | 0.0412 (11) | −0.0210 (11) | −0.0140 (9) | 0.0029 (10) |
C21 | 0.0535 (14) | 0.0615 (14) | 0.0487 (12) | −0.0068 (11) | −0.0120 (10) | −0.0134 (10) |
C22 | 0.0476 (13) | 0.0459 (12) | 0.0496 (12) | −0.0021 (10) | −0.0162 (10) | −0.0021 (9) |
C23 | 0.0345 (12) | 0.0652 (14) | 0.0609 (14) | 0.0055 (11) | −0.0160 (10) | 0.0010 (11) |
C24 | 0.0452 (13) | 0.0592 (13) | 0.0532 (13) | 0.0027 (11) | −0.0114 (10) | 0.0120 (11) |
C25 | 0.0553 (15) | 0.098 (2) | 0.0529 (14) | −0.0252 (13) | −0.0229 (12) | 0.0029 (13) |
N1—C8 | 1.374 (3) | C10—C11 | 1.380 (3) |
N1—C1 | 1.383 (2) | C10—H10 | 0.9300 |
N1—C4 | 1.402 (2) | C11—C12 | 1.365 (3) |
N2—C24 | 1.330 (2) | C11—H11 | 0.9300 |
N2—N3 | 1.364 (2) | C12—C13 | 1.371 (3) |
N2—C16 | 1.427 (2) | C12—H12 | 0.9300 |
N3—C23 | 1.308 (2) | C13—C14 | 1.386 (3) |
N4—C24 | 1.308 (3) | C13—H13 | 0.9300 |
N4—C23 | 1.351 (3) | C14—H14 | 0.9300 |
N5—C25 | 1.138 (3) | C15—C16 | 1.337 (3) |
C1—C2 | 1.395 (3) | C15—H15 | 0.9300 |
C1—C15 | 1.446 (3) | C16—C17 | 1.474 (3) |
C2—C3 | 1.397 (3) | C17—C18 | 1.391 (2) |
C2—C9 | 1.474 (3) | C17—C22 | 1.393 (3) |
C3—C4 | 1.390 (3) | C18—C19 | 1.373 (3) |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.403 (3) | C19—C20 | 1.386 (3) |
C5—C6 | 1.350 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.377 (3) |
C6—C7 | 1.413 (3) | C20—C25 | 1.439 (3) |
C6—H6 | 0.9300 | C21—C22 | 1.377 (3) |
C7—C8 | 1.348 (3) | C21—H21 | 0.9300 |
C7—H7 | 0.9300 | C22—H22 | 0.9300 |
C8—H8 | 0.9300 | C23—H23 | 0.9300 |
C9—C10 | 1.387 (3) | C24—H24 | 0.9300 |
C9—C14 | 1.388 (3) | ||
C8—N1—C1 | 128.76 (17) | C11—C12—C13 | 119.6 (2) |
C8—N1—C4 | 121.32 (17) | C11—C12—H12 | 120.2 |
C1—N1—C4 | 109.75 (16) | C13—C12—H12 | 120.2 |
C24—N2—N3 | 108.51 (16) | C12—C13—C14 | 120.3 (2) |
C24—N2—C16 | 129.20 (17) | C12—C13—H13 | 119.9 |
N3—N2—C16 | 122.18 (15) | C14—C13—H13 | 119.9 |
C23—N3—N2 | 102.02 (16) | C13—C14—C9 | 120.7 (2) |
C24—N4—C23 | 101.48 (18) | C13—C14—H14 | 119.7 |
N1—C1—C2 | 107.01 (16) | C9—C14—H14 | 119.7 |
N1—C1—C15 | 120.65 (17) | C16—C15—C1 | 125.28 (17) |
C2—C1—C15 | 132.28 (18) | C16—C15—H15 | 117.4 |
C1—C2—C3 | 108.12 (18) | C1—C15—H15 | 117.4 |
C1—C2—C9 | 125.41 (17) | C15—C16—N2 | 116.93 (16) |
C3—C2—C9 | 126.46 (18) | C15—C16—C17 | 127.03 (17) |
C4—C3—C2 | 108.75 (17) | N2—C16—C17 | 116.00 (15) |
C4—C3—H3 | 125.6 | C18—C17—C22 | 118.07 (17) |
C2—C3—H3 | 125.6 | C18—C17—C16 | 120.82 (17) |
C3—C4—N1 | 106.36 (17) | C22—C17—C16 | 121.10 (16) |
C3—C4—C5 | 135.6 (2) | C19—C18—C17 | 121.42 (19) |
N1—C4—C5 | 118.1 (2) | C19—C18—H18 | 119.3 |
C6—C5—C4 | 120.3 (2) | C17—C18—H18 | 119.3 |
C6—C5—H5 | 119.8 | C18—C19—C20 | 119.70 (18) |
C4—C5—H5 | 119.8 | C18—C19—H19 | 120.2 |
C5—C6—C7 | 120.1 (2) | C20—C19—H19 | 120.2 |
C5—C6—H6 | 120.0 | C21—C20—C19 | 119.68 (18) |
C7—C6—H6 | 120.0 | C21—C20—C25 | 119.9 (2) |
C8—C7—C6 | 120.6 (2) | C19—C20—C25 | 120.4 (2) |
C8—C7—H7 | 119.7 | C20—C21—C22 | 120.5 (2) |
C6—C7—H7 | 119.7 | C20—C21—H21 | 119.7 |
C7—C8—N1 | 119.5 (2) | C22—C21—H21 | 119.7 |
C7—C8—H8 | 120.2 | C21—C22—C17 | 120.59 (19) |
N1—C8—H8 | 120.2 | C21—C22—H22 | 119.7 |
C10—C9—C14 | 118.0 (2) | C17—C22—H22 | 119.7 |
C10—C9—C2 | 120.40 (18) | N3—C23—N4 | 115.99 (19) |
C14—C9—C2 | 121.62 (18) | N3—C23—H23 | 122.0 |
C11—C10—C9 | 120.9 (2) | N4—C23—H23 | 122.0 |
C11—C10—H10 | 119.6 | N4—C24—N2 | 112.00 (19) |
C9—C10—H10 | 119.6 | N4—C24—H24 | 124.0 |
C12—C11—C10 | 120.5 (2) | N2—C24—H24 | 124.0 |
C12—C11—H11 | 119.7 | N5—C25—C20 | 179.4 (3) |
C10—C11—H11 | 119.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N5i | 0.93 | 2.54 | 3.448 (3) | 165 |
C19—H19···N3ii | 0.93 | 2.62 | 3.462 (3) | 152 |
C24—H24···N4iii | 0.93 | 2.67 | 3.492 (3) | 148 |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+2; (iii) −x, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C25H17N5 |
Mr | 387.44 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1010.2 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.58 × 0.50 × 0.37 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.956, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5230, 3492, 2413 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.122, 1.02 |
No. of reflections | 3492 |
No. of parameters | 272 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.19 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N5i | 0.93 | 2.54 | 3.448 (3) | 164.8 |
C19—H19···N3ii | 0.93 | 2.62 | 3.462 (3) | 151.7 |
C24—H24···N4iii | 0.93 | 2.67 | 3.492 (3) | 147.6 |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z+2; (iii) −x, −y+2, −z+1. |
Centroids | Centroid-to-centroid | Plane-to-plane | Slippage |
Cg1···Cg2i | 3.724 (2) | 3.622 | 0.867 |
Cg3···Cg4 | 3.724 (2) | 3.536 | 1.168 |
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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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.