Acta Cryst. (2008). E64, o1891 [ doi:10.1107/S1600536808027669 ]
The title compound, C25H16Cl2N4, has intramolecular N-H
N and C-HCl hydrogen bonds. In the crystal structure, molecules are linked through N-HN hydrogen bonds, forming a centrosymmetric R22(16) dimer.
A mixture of 3-cyanoacetyl indole (1 mmol), 2,4 dichlorobenzaldehyde (1 mmol) and 2-acetyl pyridine (1 mmol) in 5 g m of ammounim acetate under neat condition was refluxed for 6–8 h. After the completion of the reaction (as monitored by TLC), it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuo. The crude product was chromatographed and isolated in 80% yield (90:10, petroleum ether: ethyl acetate). The crude was recrystallized in ethanol
H atoms bonded to C were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The H atoms bonded to N were freely refined.
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).
![[Figure 1]](./bt2767fig1thm.gif)
| Fig. 1. Perspective view of the molecules showing the thermal ellipsoids are drawn at 50% probability level. The H atoms are shown as small circles of arbitrary radii. |
| C25H16Cl2N4 | Z = 2 |
| Mr = 443.32 | F(000) = 456 |
| Triclinic, P1 | Dx = 1.379 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.0158 (9) Å | Cell parameters from 2900 reflections |
| b = 10.0261 (12) Å | θ = 2.2–25.0° |
| c = 14.3653 (17) Å | µ = 0.33 mm−1 |
| α = 72.260 (6)° | T = 298 K |
| β = 79.420 (6)° | Block, yellow |
| γ = 78.224 (6)° | 0.35 × 0.32 × 0.28 mm |
| V = 1067.3 (2) Å3 |
| Bruker APEX2 CCD area-detector diffractometer | 3707 independent reflections |
| Radiation source: fine-focus sealed tube | 3172 reflections with I > 2σ(I) |
| graphite | Rint = 0.023 |
| ω and φ scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −9→7 |
| Tmin = 0.895, Tmax = 0.915 | k = −11→11 |
| 12383 measured reflections | l = −17→16 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.08 | w = 1/[σ2(Fo2) + (0.0719P)2 + 0.5551P] where P = (Fo2 + 2Fc2)/3 |
| 3707 reflections | (Δ/σ)max = 0.001 |
| 288 parameters | Δρmax = 0.61 e Å−3 |
| 0 restraints | Δρmin = −0.64 e Å−3 |
| C25H16Cl2N4 | γ = 78.224 (6)° |
| Mr = 443.32 | V = 1067.3 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.0158 (9) Å | Mo Kα radiation |
| b = 10.0261 (12) Å | µ = 0.33 mm−1 |
| c = 14.3653 (17) Å | T = 298 K |
| α = 72.260 (6)° | 0.35 × 0.32 × 0.28 mm |
| β = 79.420 (6)° |
| Bruker APEX2 CCD area-detector diffractometer | 3707 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 3172 reflections with I > 2σ(I) |
| Tmin = 0.895, Tmax = 0.915 | Rint = 0.023 |
| 12383 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.140 | Δρmax = 0.61 e Å−3 |
| S = 1.08 | Δρmin = −0.64 e Å−3 |
| 3707 reflections | Absolute structure: ? |
| 288 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| Cl1 | 0.65524 (10) | 0.88516 (11) | 0.55182 (6) | 0.0861 (3) | |
| Cl2 | 1.32340 (10) | 0.67807 (10) | 0.50447 (5) | 0.0832 (3) | |
| N1 | 0.7936 (2) | 0.98325 (19) | 0.91511 (14) | 0.0411 (4) | |
| H1 | 0.821 (3) | 0.993 (3) | 0.966 (2) | 0.055 (8)* | |
| C2 | 0.7078 (3) | 0.8757 (2) | 0.92099 (15) | 0.0342 (4) | |
| C3 | 0.6640 (3) | 0.8668 (2) | 0.83578 (15) | 0.0362 (5) | |
| C4 | 0.7222 (3) | 0.9620 (2) | 0.73464 (15) | 0.0373 (5) | |
| H4 | 0.6248 | 0.9910 | 0.6966 | 0.045* | |
| C5 | 0.7668 (3) | 1.0937 (2) | 0.74732 (16) | 0.0412 (5) | |
| H5 | 0.7692 | 1.1738 | 0.6936 | 0.049* | |
| C6 | 0.8027 (3) | 1.0996 (2) | 0.83236 (15) | 0.0359 (5) | |
| C7 | 0.6707 (3) | 0.7807 (2) | 1.01918 (15) | 0.0357 (5) | |
| C8 | 0.6776 (3) | 0.8008 (2) | 1.11452 (15) | 0.0355 (4) | |
| C9 | 0.7107 (3) | 0.9087 (2) | 1.14899 (17) | 0.0426 (5) | |
| H9 | 0.7337 | 0.9946 | 1.1049 | 0.051* | |
| C10 | 0.7087 (3) | 0.8860 (3) | 1.24827 (18) | 0.0515 (6) | |
| H10 | 0.7316 | 0.9572 | 1.2709 | 0.062* | |
| C11 | 0.6732 (3) | 0.7589 (3) | 1.31624 (18) | 0.0553 (6) | |
| H11 | 0.6743 | 0.7465 | 1.3830 | 0.066* | |
| C12 | 0.6369 (3) | 0.6519 (3) | 1.28621 (17) | 0.0523 (6) | |
| H12 | 0.6108 | 0.5677 | 1.3314 | 0.063* | |
| C13 | 0.6405 (3) | 0.6741 (2) | 1.18565 (16) | 0.0408 (5) | |
| N14 | 0.6121 (3) | 0.5841 (2) | 1.13699 (14) | 0.0475 (5) | |
| H14 | 0.586 (3) | 0.503 (3) | 1.1635 (19) | 0.050 (7)* | |
| C15 | 0.6302 (3) | 0.6468 (2) | 1.03934 (16) | 0.0430 (5) | |
| H15 | 0.6172 | 0.6054 | 0.9919 | 0.052* | |
| C16 | 0.5542 (3) | 0.7736 (2) | 0.83477 (16) | 0.0433 (5) | |
| N17 | 0.4654 (3) | 0.7028 (2) | 0.82628 (17) | 0.0636 (6) | |
| C18 | 0.8703 (3) | 0.8858 (2) | 0.67753 (15) | 0.0365 (5) | |
| C19 | 0.8534 (3) | 0.8496 (3) | 0.59441 (17) | 0.0455 (5) | |
| C20 | 0.9908 (3) | 0.7851 (3) | 0.54127 (18) | 0.0548 (6) | |
| H20 | 0.9761 | 0.7629 | 0.4853 | 0.066* | |
| C21 | 1.1491 (3) | 0.7547 (3) | 0.57292 (17) | 0.0522 (6) | |
| C22 | 1.1726 (3) | 0.7853 (3) | 0.65559 (18) | 0.0537 (6) | |
| H22 | 1.2802 | 0.7628 | 0.6770 | 0.064* | |
| C23 | 1.0333 (3) | 0.8503 (3) | 0.70659 (17) | 0.0474 (6) | |
| H23 | 1.0492 | 0.8713 | 0.7628 | 0.057* | |
| C24 | 0.8451 (3) | 1.2263 (2) | 0.85058 (16) | 0.0382 (5) | |
| C25 | 0.8700 (4) | 1.3490 (2) | 0.77569 (19) | 0.0540 (6) | |
| H25 | 0.8621 | 1.3543 | 0.7108 | 0.065* | |
| C26 | 0.9063 (4) | 1.4627 (3) | 0.7986 (2) | 0.0614 (7) | |
| H26 | 0.9234 | 1.5458 | 0.7495 | 0.074* | |
| C27 | 0.9171 (3) | 1.4520 (3) | 0.8944 (2) | 0.0580 (7) | |
| H27 | 0.9407 | 1.5276 | 0.9119 | 0.070* | |
| C28 | 0.8923 (3) | 1.3271 (3) | 0.9640 (2) | 0.0560 (6) | |
| H28 | 0.9000 | 1.3201 | 1.0292 | 0.067* | |
| N29 | 0.8574 (3) | 1.2145 (2) | 0.94397 (14) | 0.0465 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0591 (4) | 0.1440 (8) | 0.0794 (5) | 0.0098 (4) | −0.0343 (4) | −0.0684 (6) |
| Cl2 | 0.0690 (5) | 0.1084 (7) | 0.0464 (4) | 0.0200 (4) | 0.0061 (3) | −0.0138 (4) |
| N1 | 0.0546 (11) | 0.0394 (10) | 0.0346 (10) | −0.0202 (8) | −0.0125 (8) | −0.0056 (8) |
| C2 | 0.0346 (10) | 0.0320 (10) | 0.0376 (11) | −0.0075 (8) | −0.0042 (8) | −0.0106 (8) |
| C3 | 0.0383 (11) | 0.0334 (11) | 0.0389 (11) | −0.0084 (8) | −0.0066 (9) | −0.0105 (9) |
| C4 | 0.0413 (11) | 0.0390 (11) | 0.0337 (11) | −0.0072 (9) | −0.0105 (8) | −0.0094 (9) |
| C5 | 0.0524 (13) | 0.0329 (11) | 0.0370 (12) | −0.0100 (9) | −0.0069 (9) | −0.0051 (9) |
| C6 | 0.0386 (11) | 0.0312 (10) | 0.0374 (11) | −0.0092 (8) | −0.0032 (8) | −0.0074 (9) |
| C7 | 0.0372 (11) | 0.0341 (10) | 0.0370 (11) | −0.0086 (8) | −0.0029 (8) | −0.0109 (9) |
| C8 | 0.0335 (10) | 0.0361 (11) | 0.0363 (11) | −0.0051 (8) | −0.0006 (8) | −0.0115 (9) |
| C9 | 0.0443 (12) | 0.0427 (12) | 0.0435 (12) | −0.0110 (10) | 0.0017 (9) | −0.0175 (10) |
| C10 | 0.0494 (13) | 0.0661 (16) | 0.0489 (14) | −0.0139 (12) | 0.0008 (10) | −0.0314 (12) |
| C11 | 0.0545 (14) | 0.0778 (18) | 0.0368 (13) | −0.0136 (13) | 0.0003 (10) | −0.0224 (12) |
| C12 | 0.0555 (14) | 0.0582 (15) | 0.0368 (12) | −0.0130 (12) | 0.0014 (10) | −0.0054 (11) |
| C13 | 0.0429 (12) | 0.0410 (12) | 0.0377 (12) | −0.0095 (9) | 0.0002 (9) | −0.0109 (9) |
| N14 | 0.0648 (13) | 0.0363 (10) | 0.0413 (11) | −0.0213 (9) | −0.0015 (9) | −0.0049 (8) |
| C15 | 0.0532 (13) | 0.0388 (12) | 0.0398 (12) | −0.0147 (10) | −0.0043 (10) | −0.0115 (9) |
| C16 | 0.0558 (13) | 0.0381 (12) | 0.0395 (12) | −0.0119 (10) | −0.0126 (10) | −0.0092 (9) |
| N17 | 0.0899 (17) | 0.0533 (13) | 0.0592 (14) | −0.0350 (12) | −0.0293 (12) | −0.0053 (10) |
| C18 | 0.0427 (11) | 0.0357 (11) | 0.0320 (11) | −0.0119 (9) | −0.0076 (8) | −0.0054 (8) |
| C19 | 0.0463 (12) | 0.0546 (14) | 0.0384 (12) | −0.0064 (10) | −0.0130 (10) | −0.0138 (10) |
| C20 | 0.0632 (16) | 0.0678 (16) | 0.0349 (12) | −0.0037 (13) | −0.0084 (11) | −0.0195 (11) |
| C21 | 0.0511 (14) | 0.0557 (15) | 0.0375 (13) | −0.0017 (11) | 0.0017 (10) | −0.0040 (11) |
| C22 | 0.0407 (12) | 0.0694 (17) | 0.0472 (14) | −0.0072 (11) | −0.0095 (10) | −0.0094 (12) |
| C23 | 0.0466 (13) | 0.0585 (14) | 0.0413 (12) | −0.0136 (11) | −0.0109 (10) | −0.0137 (11) |
| C24 | 0.0368 (11) | 0.0352 (11) | 0.0431 (12) | −0.0078 (9) | −0.0011 (9) | −0.0129 (9) |
| C25 | 0.0737 (17) | 0.0415 (13) | 0.0481 (14) | −0.0196 (12) | −0.0043 (12) | −0.0095 (11) |
| C26 | 0.0767 (18) | 0.0367 (13) | 0.0698 (18) | −0.0200 (12) | −0.0008 (14) | −0.0111 (12) |
| C27 | 0.0606 (16) | 0.0446 (14) | 0.0786 (19) | −0.0162 (12) | −0.0004 (13) | −0.0313 (13) |
| C28 | 0.0643 (16) | 0.0558 (15) | 0.0594 (16) | −0.0184 (12) | −0.0043 (12) | −0.0293 (13) |
| N29 | 0.0549 (11) | 0.0451 (11) | 0.0461 (11) | −0.0165 (9) | −0.0044 (9) | −0.0178 (9) |
| Cl1—C19 | 1.737 (2) | C12—H12 | 0.9300 |
| Cl2—C21 | 1.740 (2) | C13—N14 | 1.372 (3) |
| N1—C2 | 1.367 (3) | N14—C15 | 1.345 (3) |
| N1—C6 | 1.392 (3) | N14—H14 | 0.84 (3) |
| N1—H1 | 0.84 (3) | C15—H15 | 0.9300 |
| C2—C3 | 1.366 (3) | C16—N17 | 1.147 (3) |
| C2—C7 | 1.459 (3) | C18—C19 | 1.385 (3) |
| C3—C16 | 1.413 (3) | C18—C23 | 1.388 (3) |
| C3—C4 | 1.526 (3) | C19—C20 | 1.384 (3) |
| C4—C5 | 1.506 (3) | C20—C21 | 1.371 (4) |
| C4—C18 | 1.524 (3) | C20—H20 | 0.9300 |
| C4—H4 | 0.9800 | C21—C22 | 1.367 (4) |
| C5—C6 | 1.326 (3) | C22—C23 | 1.379 (3) |
| C5—H5 | 0.9300 | C22—H22 | 0.9300 |
| C6—C24 | 1.487 (3) | C23—H23 | 0.9300 |
| C7—C15 | 1.377 (3) | C24—N29 | 1.331 (3) |
| C7—C8 | 1.456 (3) | C24—C25 | 1.388 (3) |
| C8—C9 | 1.407 (3) | C25—C26 | 1.376 (3) |
| C8—C13 | 1.413 (3) | C25—H25 | 0.9300 |
| C9—C10 | 1.372 (3) | C26—C27 | 1.364 (4) |
| C9—H9 | 0.9300 | C26—H26 | 0.9300 |
| C10—C11 | 1.395 (4) | C27—C28 | 1.369 (4) |
| C10—H10 | 0.9300 | C27—H27 | 0.9300 |
| C11—C12 | 1.370 (4) | C28—N29 | 1.339 (3) |
| C11—H11 | 0.9300 | C28—H28 | 0.9300 |
| C12—C13 | 1.389 (3) | ||
| C2—N1—C6 | 122.28 (18) | C15—N14—C13 | 109.48 (19) |
| C2—N1—H1 | 120.3 (19) | C15—N14—H14 | 124.8 (17) |
| C6—N1—H1 | 115.6 (19) | C13—N14—H14 | 125.8 (17) |
| C3—C2—N1 | 117.87 (18) | N14—C15—C7 | 110.8 (2) |
| C3—C2—C7 | 125.98 (18) | N14—C15—H15 | 124.6 |
| N1—C2—C7 | 116.15 (18) | C7—C15—H15 | 124.6 |
| C2—C3—C16 | 122.62 (19) | N17—C16—C3 | 174.7 (2) |
| C2—C3—C4 | 122.64 (17) | C19—C18—C23 | 116.2 (2) |
| C16—C3—C4 | 114.67 (18) | C19—C18—C4 | 123.25 (19) |
| C5—C4—C18 | 111.94 (17) | C23—C18—C4 | 120.57 (19) |
| C5—C4—C3 | 108.98 (16) | C20—C19—C18 | 122.5 (2) |
| C18—C4—C3 | 112.45 (17) | C20—C19—Cl1 | 116.87 (17) |
| C5—C4—H4 | 107.8 | C18—C19—Cl1 | 120.65 (18) |
| C18—C4—H4 | 107.8 | C21—C20—C19 | 118.6 (2) |
| C3—C4—H4 | 107.8 | C21—C20—H20 | 120.7 |
| C6—C5—C4 | 122.38 (19) | C19—C20—H20 | 120.7 |
| C6—C5—H5 | 118.8 | C22—C21—C20 | 121.4 (2) |
| C4—C5—H5 | 118.8 | C22—C21—Cl2 | 119.8 (2) |
| C5—C6—N1 | 120.15 (18) | C20—C21—Cl2 | 118.7 (2) |
| C5—C6—C24 | 125.28 (19) | C21—C22—C23 | 118.6 (2) |
| N1—C6—C24 | 114.49 (18) | C21—C22—H22 | 120.7 |
| C15—C7—C8 | 105.65 (18) | C23—C22—H22 | 120.7 |
| C15—C7—C2 | 125.51 (19) | C22—C23—C18 | 122.7 (2) |
| C8—C7—C2 | 128.75 (18) | C22—C23—H23 | 118.6 |
| C9—C8—C13 | 117.36 (19) | C18—C23—H23 | 118.6 |
| C9—C8—C7 | 136.58 (19) | N29—C24—C25 | 122.0 (2) |
| C13—C8—C7 | 106.06 (18) | N29—C24—C6 | 115.44 (18) |
| C10—C9—C8 | 119.2 (2) | C25—C24—C6 | 122.6 (2) |
| C10—C9—H9 | 120.4 | C26—C25—C24 | 119.1 (2) |
| C8—C9—H9 | 120.4 | C26—C25—H25 | 120.4 |
| C9—C10—C11 | 121.7 (2) | C24—C25—H25 | 120.4 |
| C9—C10—H10 | 119.1 | C27—C26—C25 | 119.2 (2) |
| C11—C10—H10 | 119.1 | C27—C26—H26 | 120.4 |
| C12—C11—C10 | 121.0 (2) | C25—C26—H26 | 120.4 |
| C12—C11—H11 | 119.5 | C26—C27—C28 | 118.2 (2) |
| C10—C11—H11 | 119.5 | C26—C27—H27 | 120.9 |
| C11—C12—C13 | 117.3 (2) | C28—C27—H27 | 120.9 |
| C11—C12—H12 | 121.3 | N29—C28—C27 | 123.9 (2) |
| C13—C12—H12 | 121.3 | N29—C28—H28 | 118.0 |
| N14—C13—C12 | 128.7 (2) | C27—C28—H28 | 118.0 |
| N14—C13—C8 | 107.98 (19) | C24—N29—C28 | 117.5 (2) |
| C12—C13—C8 | 123.3 (2) | ||
| C6—N1—C2—C3 | 15.0 (3) | C8—C13—N14—C15 | 0.3 (3) |
| C6—N1—C2—C7 | −164.76 (19) | C13—N14—C15—C7 | −0.2 (3) |
| N1—C2—C3—C16 | −170.6 (2) | C8—C7—C15—N14 | 0.0 (3) |
| C7—C2—C3—C16 | 9.1 (3) | C2—C7—C15—N14 | 176.8 (2) |
| N1—C2—C3—C4 | 6.2 (3) | C2—C3—C16—N17 | 173 (3) |
| C7—C2—C3—C4 | −174.09 (19) | C4—C3—C16—N17 | −4(3) |
| C2—C3—C4—C5 | −22.1 (3) | C5—C4—C18—C19 | −126.6 (2) |
| C16—C3—C4—C5 | 154.91 (19) | C3—C4—C18—C19 | 110.4 (2) |
| C2—C3—C4—C18 | 102.6 (2) | C5—C4—C18—C23 | 52.5 (3) |
| C16—C3—C4—C18 | −80.4 (2) | C3—C4—C18—C23 | −70.6 (2) |
| C18—C4—C5—C6 | −104.9 (2) | C23—C18—C19—C20 | −1.6 (3) |
| C3—C4—C5—C6 | 20.1 (3) | C4—C18—C19—C20 | 177.5 (2) |
| C4—C5—C6—N1 | −2.5 (3) | C23—C18—C19—Cl1 | 178.79 (17) |
| C4—C5—C6—C24 | −179.03 (19) | C4—C18—C19—Cl1 | −2.1 (3) |
| C2—N1—C6—C5 | −17.2 (3) | C18—C19—C20—C21 | 0.7 (4) |
| C2—N1—C6—C24 | 159.66 (19) | Cl1—C19—C20—C21 | −179.7 (2) |
| C3—C2—C7—C15 | 19.2 (3) | C19—C20—C21—C22 | 0.7 (4) |
| N1—C2—C7—C15 | −161.1 (2) | C19—C20—C21—Cl2 | −178.27 (19) |
| C3—C2—C7—C8 | −164.7 (2) | C20—C21—C22—C23 | −1.1 (4) |
| N1—C2—C7—C8 | 15.0 (3) | Cl2—C21—C22—C23 | 177.89 (19) |
| C15—C7—C8—C9 | 180.0 (2) | C21—C22—C23—C18 | 0.1 (4) |
| C2—C7—C8—C9 | 3.3 (4) | C19—C18—C23—C22 | 1.2 (3) |
| C15—C7—C8—C13 | 0.2 (2) | C4—C18—C23—C22 | −177.9 (2) |
| C2—C7—C8—C13 | −176.5 (2) | C5—C6—C24—N29 | 172.5 (2) |
| C13—C8—C9—C10 | 1.2 (3) | N1—C6—C24—N29 | −4.2 (3) |
| C7—C8—C9—C10 | −178.6 (2) | C5—C6—C24—C25 | −7.3 (4) |
| C8—C9—C10—C11 | −0.6 (4) | N1—C6—C24—C25 | 176.0 (2) |
| C9—C10—C11—C12 | −0.8 (4) | N29—C24—C25—C26 | −0.8 (4) |
| C10—C11—C12—C13 | 1.4 (4) | C6—C24—C25—C26 | 179.0 (2) |
| C11—C12—C13—N14 | 178.8 (2) | C24—C25—C26—C27 | 0.0 (4) |
| C11—C12—C13—C8 | −0.7 (4) | C25—C26—C27—C28 | 0.5 (4) |
| C9—C8—C13—N14 | 179.84 (19) | C26—C27—C28—N29 | −0.2 (4) |
| C7—C8—C13—N14 | −0.3 (2) | C25—C24—N29—C28 | 1.1 (3) |
| C9—C8—C13—C12 | −0.6 (3) | C6—C24—N29—C28 | −178.8 (2) |
| C7—C8—C13—C12 | 179.3 (2) | C27—C28—N29—C24 | −0.6 (4) |
| C12—C13—N14—C15 | −179.2 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N29 | 0.85 (3) | 2.21 (3) | 2.638 (2) | 111 (2) |
| C4—H4···Cl1 | 0.98 | 2.56 | 3.114 (2) | 116. |
| N14—H14···N17i | 0.84 (3) | 2.14 (3) | 2.937 (3) | 158 (2) |
| Symmetry codes: (i) −x+1, −y+1, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N29 | 0.85 (3) | 2.21 (3) | 2.638 (2) | 111 (2) |
| C4—H4···Cl1 | 0.98 | 2.56 | 3.114 (2) | 116. |
| N14—H14···N17i | 0.84 (3) | 2.14 (3) | 2.937 (3) | 158 (2) |
| Symmetry codes: (i) −x+1, −y+1, −z+2. |
PR thanks V. Ramkumar, Department of Chemistry, IIT, Madras, India, for his help with the data collection.
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Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle 1960; Ho et al., 1986). Indoles also have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al.., 1999). In view of these biological importance, an X-ray diffraction study of the title compound, (I), was carrid out.
The pyridine ring A adopts a planar conformation. The planar indole ring system and the pyridine ring E lie in the plane of pyridine ring A. The bond angle of (C3—C16—N17) 174.7 (2)° shows linear character of the cyano group, a feature observed in carbonitrile compounds. The sum of the angles at N1 of the pyridine ring (358.16°) is in accordance with sp2 hybridization (Beddoes et al., 1986).
The crystal structure is stabilized by N—H···N interactions. Atom N1 donates a proton to atom N29 and it forms a S(5) ring motif (Bernstein et al., 1995). The molecules at positions (x, y, z) and (1 - x,1 - y,-z) form a cyclic centrosymmetric R22(16) dimer through N14—H14···N17 hydrogen bonds.