organic compounds
5-(2-Hydroxybenzoyl)-2-(1H-indol-3-yl)pyridine-3-carbonitrile
aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamil Nadu, India, bOrganic Chemistry Division, CSIR Central Leather Research Institute, Chennai 600 020, Tamil Nadu, India, and cPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com
In the title compound, C21H13N3O2, the indole and pyridine rings are planar. The pyridine ring is in an antiperiplanar (−ap) orientation with the indole ring system and an antiperiplanar (+ap) orientation with the hydroxyphenyl ring. An intramolecular O—H⋯O hydrogen bond stabilizes the molecular structure. In the crystal, N—H⋯N hydrogen bonds involving the indole NH group and the cyanide nitrogen atom lead to the formation of a two-dimensional supramolecular network lying parallel to (011).
Keywords: crystal structure; indole; hydrogen bonding.
CCDC reference: 1472998
Structure description
Indole ring systems have become an important structural component in many pharmaceutical agents (Sundberg, 1996). Substituted indoles have been refered to as privileged structures since they are capable of binding to many receptors with high affinity (Evans et al., 1988). Some indole derivatives possess cytotoxic activity (Muratake et al., 1994). Indole and its bioisosters and derivatives have antimicrobial activity against Gram-negative and Gram-positive bacteria, the yeast Candida albicans and Enterobacter, Pseudomonas aeruginosa, E. coli, and Staphylococcus epidermidis (Biswal et al., 2012).
The structure of the title compound is shown in Fig. 1. The C—N distances range from 1.345 (2) to 1.370 (2) Å, and are in good agreement with the related reported values (Vishnupriya et al., 2014). The C14—O1 and C21—N3 bond lengths are 1.2347 (14) Å and 1.1413 (16) Å, respectively, in agreement with values reported by Vimala et al. (2015), confirming the presence of double and triple bonds. The pyridine ring (C9/N2/C10–C13) is in an antiperiplanar (−ap) orientation with the indole ring system (C1/N1/C2–C8) and in an antiperiplanar (+ap) orientation with the hydroxyphenyl ring (C15–C20), as evidenced by the torsion angles C7—C8—C9—C13 = −163.54 (11)° and C10—C11—C14—C15 = 155.15 (11)°, respectively. An intramolecular O—H⋯O hydrogen bond (Table 1) stabilizes the molecular structure.
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In the crystal, N—H⋯N hydrogen bonds (Table 1) between the indole NH group and the cyanide nitrogen atom result in a two-dimensional supramolecular network lying parallel to (011) (Fig. 2).
Synthesis and crystallization
A mixture of 3-formylchromone (1 mmol), cyanoacetylindole (1 mmol) and ammonium acetate (1 mmol) in DMF and a catalytic amount of SnCl2·2H2O (0.020 mol%) was added and refluxed for about 3 h. After completion of the reaction, the solvent was removed under reduced pressure and the residue was purified by on siliga gel (3:97% ethyl acetate and petetroleum ether) to afford pure product in 94% yield. The purified compound was recrystallized from ethanol through slow evaporation of the solvent.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1472998
10.1107/S2414314616005861/hg4004sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005861/hg4004Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005861/hg4004Isup3.cml
A mixture of 3-formylchromone (1 mmol), cyanoacetylindole (1 mmol) and ammonium acetate (1 mmol) in DMF and a catalytic amount of SnCl2·2H2O (0.020 mol%) was added and refluxed for about 3 h. After completion of the reaction, the solvent was removed under reduced pressure and the residue was purified by
on siliga gel (3:97% ethyl acetate and petetroleum ether) to afford pure product in 94% yield. The purified compound was recrystallized from ethanol through slow evaporation of the solvent.Indole ring systems have become an important structural component in many pharmaceutical agents (Sundberg, 1996). Substituted indoles have been refered to as privileged structures since they are capable of binding to many receptors with high affinity (Evans et al., 1988). Some indole derivatives possess cytotoxic activity (Muratake et al., 1994). Indole and its bioisosters and derivatives have antimicrobial activity against Gram-negative and Gram-positive bacteria, the yeast Candida albicans and Enterobacter, Pseudomonas aeruginosa, E. coli, and Staphylococcus epidermidis (Biswal et al., 2012).
The structure of the title compound is shown in Fig. 1. The C—N distances range from 1.345 (2) to 1.370 (2) Å, and are in good agreement with the related reported values (Vishnupriya et al., 2014). The C14—O1 and C21—N3 bond lengths are 1.2347 (14) Å and 1.1413 (16) Å, respectively, in agreement with values reported by Vimala et al. (2015), confirming the presence of double and triple bonds. The pyridine ring (C9/N2/C10–C13) is in an antiperiplanar (-ap) orientation with the indole ring system (C1/N1/C2–C8) and in an antiperiplanar(+ap) orientation with the hydroxyphenyl ring (C15–C20), as evidenced by the torsion angles C7—C8—C9—C13 = -163.54 (11)° and C10—C11—C14—C15 = 155.15 (11)°, respectively. An intramolecular O—H···O hydrogen bond (Table 1) stabilizes the molecular structure.
In the crystal, N—H···N hydrogen bonds (Table 1) between the indole NH group and the cyanide nitrogen atom result in a two-dimensional supramolecular network lying parallel to (011) (Fig. 2).
For biological activity, see: Sundberg(1996); Muratake et al.,(1994) and Biswal et al.,(2012). For related structures see: Vimala et al.,(2015) and Vishnupriya et al., (2014).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. | |
Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate hydrogen bonds. |
C21H13N3O2 | F(000) = 704 |
Mr = 339.34 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2665 reflections |
a = 12.4764 (6) Å | θ = 1.6–28.4° |
b = 7.8471 (3) Å | µ = 0.09 mm−1 |
c = 16.7265 (8) Å | T = 298 K |
β = 90.478 (2)° | Block, colorless |
V = 1637.53 (13) Å3 | 0.35 × 0.28 × 0.15 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 4105 independent reflections |
Radiation source: fine-focus sealed tube | 2665 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω and φ scan | θmax = 28.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −16→13 |
Tmin = 0.969, Tmax = 0.986 | k = −10→9 |
10911 measured reflections | l = −22→15 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.57 | (Δ/σ)max = 0.020 |
4105 reflections | Δρmax = 0.19 e Å−3 |
237 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0087 (17) |
C21H13N3O2 | V = 1637.53 (13) Å3 |
Mr = 339.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4764 (6) Å | µ = 0.09 mm−1 |
b = 7.8471 (3) Å | T = 298 K |
c = 16.7265 (8) Å | 0.35 × 0.28 × 0.15 mm |
β = 90.478 (2)° |
Bruker Kappa APEXII CCD diffractometer | 4105 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2665 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.986 | Rint = 0.019 |
10911 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.57 | Δρmax = 0.19 e Å−3 |
4105 reflections | Δρmin = −0.17 e Å−3 |
237 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | ||
C1 | 0.53477 (11) | 0.87467 (16) | −0.13362 (8) | 0.0454 (3) | |
H1 | 0.4722 | 0.8559 | −0.1629 | 0.054* | |
C2 | 0.69959 (10) | 0.96028 (15) | −0.10314 (8) | 0.0443 (3) | |
C3 | 0.80237 (11) | 1.02854 (18) | −0.10597 (10) | 0.0611 (4) | |
H3 | 0.8296 | 1.0746 | −0.1528 | 0.073* | |
C4 | 0.86139 (12) | 1.0249 (2) | −0.03697 (12) | 0.0765 (5) | |
H4 | 0.9300 | 1.0710 | −0.0364 | 0.092* | |
C5 | 0.82078 (12) | 0.9534 (2) | 0.03258 (11) | 0.0775 (6) | |
H5 | 0.8632 | 0.9525 | 0.0786 | 0.093* | |
C6 | 0.71998 (10) | 0.88427 (19) | 0.03513 (9) | 0.0574 (4) | |
H6 | 0.6944 | 0.8362 | 0.0821 | 0.069* | |
C7 | 0.65674 (10) | 0.88730 (15) | −0.03363 (8) | 0.0407 (3) | |
C8 | 0.54967 (9) | 0.82906 (14) | −0.05491 (7) | 0.0364 (3) | |
C9 | 0.47648 (9) | 0.74161 (13) | −0.00264 (7) | 0.0345 (3) | |
C10 | 0.43851 (9) | 0.66464 (15) | 0.12686 (7) | 0.0409 (3) | |
H10 | 0.4578 | 0.6690 | 0.1807 | 0.049* | |
C11 | 0.34536 (9) | 0.57542 (15) | 0.10706 (7) | 0.0376 (3) | |
C12 | 0.32069 (9) | 0.56672 (15) | 0.02623 (7) | 0.0392 (3) | |
H12 | 0.2611 | 0.5054 | 0.0089 | 0.047* | |
C13 | 0.38481 (9) | 0.64939 (14) | −0.02888 (7) | 0.0364 (3) | |
C14 | 0.28746 (11) | 0.48524 (15) | 0.17204 (8) | 0.0430 (3) | |
C15 | 0.17239 (10) | 0.44727 (16) | 0.16690 (7) | 0.0424 (3) | |
C16 | 0.12797 (11) | 0.32598 (17) | 0.21906 (9) | 0.0510 (4) | |
C17 | 0.02012 (12) | 0.2849 (2) | 0.21349 (10) | 0.0673 (5) | |
H17 | −0.0082 | 0.2017 | 0.2468 | 0.081* | |
C18 | −0.04463 (13) | 0.3656 (2) | 0.15956 (11) | 0.0717 (5) | |
H18 | −0.1169 | 0.3368 | 0.1564 | 0.086* | |
C19 | −0.00423 (11) | 0.4898 (2) | 0.10947 (9) | 0.0632 (4) | |
H19 | −0.0493 | 0.5464 | 0.0738 | 0.076* | |
C20 | 0.10269 (11) | 0.52865 (18) | 0.11289 (8) | 0.0498 (4) | |
H20 | 0.1298 | 0.6110 | 0.0786 | 0.060* | |
C21 | 0.35909 (10) | 0.62929 (17) | −0.11168 (8) | 0.0438 (3) | |
N1 | 0.62325 (9) | 0.95015 (13) | −0.16227 (6) | 0.0499 (3) | |
H1A | 0.6308 | 0.9865 | −0.2104 | 0.060* | |
N2 | 0.50172 (8) | 0.74344 (12) | 0.07581 (6) | 0.0392 (3) | |
N3 | 0.33755 (10) | 0.60956 (18) | −0.17749 (7) | 0.0645 (4) | |
O1 | 0.34049 (8) | 0.44114 (13) | 0.23117 (6) | 0.0621 (3) | |
O2 | 0.18699 (9) | 0.24606 (14) | 0.27537 (7) | 0.0697 (3) | |
H2 | 0.2482 | 0.2840 | 0.2753 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0571 (8) | 0.0470 (7) | 0.0320 (8) | −0.0046 (6) | 0.0009 (6) | −0.0008 (5) |
C2 | 0.0465 (8) | 0.0416 (7) | 0.0451 (9) | 0.0062 (5) | 0.0104 (6) | 0.0042 (5) |
C3 | 0.0499 (9) | 0.0560 (9) | 0.0778 (12) | 0.0058 (6) | 0.0199 (8) | 0.0196 (7) |
C4 | 0.0375 (8) | 0.0842 (12) | 0.1078 (15) | −0.0035 (7) | −0.0015 (9) | 0.0368 (10) |
C5 | 0.0478 (9) | 0.0969 (12) | 0.0875 (14) | −0.0088 (8) | −0.0205 (9) | 0.0371 (10) |
C6 | 0.0441 (8) | 0.0715 (9) | 0.0564 (10) | −0.0035 (6) | −0.0074 (7) | 0.0228 (7) |
C7 | 0.0402 (7) | 0.0400 (6) | 0.0419 (8) | 0.0065 (5) | 0.0047 (6) | 0.0050 (5) |
C8 | 0.0402 (7) | 0.0386 (6) | 0.0305 (7) | 0.0043 (5) | 0.0017 (5) | −0.0006 (5) |
C9 | 0.0381 (6) | 0.0364 (6) | 0.0291 (7) | 0.0063 (5) | 0.0006 (5) | −0.0018 (5) |
C10 | 0.0465 (7) | 0.0479 (7) | 0.0282 (7) | 0.0030 (5) | −0.0016 (6) | 0.0013 (5) |
C11 | 0.0410 (7) | 0.0396 (6) | 0.0324 (7) | 0.0033 (5) | 0.0039 (5) | −0.0006 (5) |
C12 | 0.0397 (7) | 0.0429 (6) | 0.0349 (8) | −0.0001 (5) | 0.0019 (6) | −0.0058 (5) |
C13 | 0.0383 (7) | 0.0421 (6) | 0.0289 (7) | 0.0044 (5) | 0.0014 (5) | −0.0046 (5) |
C14 | 0.0524 (8) | 0.0439 (7) | 0.0327 (8) | 0.0001 (5) | 0.0032 (6) | −0.0010 (5) |
C15 | 0.0483 (7) | 0.0458 (7) | 0.0332 (8) | −0.0002 (5) | 0.0100 (6) | −0.0021 (5) |
C16 | 0.0582 (9) | 0.0535 (7) | 0.0415 (9) | 0.0012 (6) | 0.0142 (7) | 0.0014 (6) |
C17 | 0.0595 (10) | 0.0708 (10) | 0.0719 (13) | −0.0104 (7) | 0.0225 (9) | 0.0100 (8) |
C18 | 0.0482 (9) | 0.0942 (13) | 0.0730 (13) | −0.0084 (8) | 0.0133 (9) | −0.0017 (10) |
C19 | 0.0504 (9) | 0.0874 (11) | 0.0521 (10) | 0.0078 (8) | 0.0042 (7) | 0.0025 (8) |
C20 | 0.0529 (8) | 0.0564 (8) | 0.0403 (8) | 0.0034 (6) | 0.0101 (6) | 0.0018 (6) |
C21 | 0.0402 (7) | 0.0572 (8) | 0.0342 (8) | −0.0042 (5) | 0.0034 (6) | −0.0070 (6) |
N1 | 0.0678 (8) | 0.0498 (6) | 0.0323 (7) | −0.0033 (5) | 0.0102 (6) | 0.0029 (5) |
N2 | 0.0430 (6) | 0.0465 (6) | 0.0282 (6) | −0.0023 (4) | −0.0006 (5) | 0.0015 (4) |
N3 | 0.0605 (8) | 0.0974 (10) | 0.0357 (8) | −0.0149 (7) | −0.0007 (6) | −0.0136 (6) |
O1 | 0.0644 (6) | 0.0780 (7) | 0.0438 (6) | −0.0103 (5) | −0.0053 (5) | 0.0185 (5) |
O2 | 0.0717 (7) | 0.0794 (7) | 0.0583 (8) | −0.0027 (6) | 0.0100 (6) | 0.0290 (6) |
C1—N1 | 1.3446 (17) | C11—C12 | 1.3857 (16) |
C1—C8 | 1.3754 (17) | C11—C14 | 1.4891 (18) |
C1—H1 | 0.9300 | C12—C13 | 1.3867 (17) |
C2—N1 | 1.3697 (16) | C12—H12 | 0.9300 |
C2—C3 | 1.3908 (19) | C13—C21 | 1.4278 (17) |
C2—C7 | 1.4057 (18) | C14—O1 | 1.2347 (14) |
C3—C4 | 1.364 (2) | C14—C15 | 1.4680 (18) |
C3—H3 | 0.9300 | C15—C20 | 1.4025 (18) |
C4—C5 | 1.391 (2) | C15—C16 | 1.4079 (19) |
C4—H4 | 0.9300 | C16—O2 | 1.3458 (16) |
C5—C6 | 1.371 (2) | C16—C17 | 1.386 (2) |
C5—H5 | 0.9300 | C17—C18 | 1.362 (2) |
C6—C7 | 1.3895 (17) | C17—H17 | 0.9300 |
C6—H6 | 0.9300 | C18—C19 | 1.383 (2) |
C7—C8 | 1.4532 (17) | C18—H18 | 0.9300 |
C8—C9 | 1.4431 (18) | C19—C20 | 1.3690 (19) |
C9—N2 | 1.3469 (15) | C19—H19 | 0.9300 |
C9—C13 | 1.4199 (16) | C20—H20 | 0.9300 |
C10—N2 | 1.3209 (16) | C21—N3 | 1.1413 (16) |
C10—C11 | 1.3943 (16) | N1—H1A | 0.8600 |
C10—H10 | 0.9300 | O2—H2 | 0.8200 |
N1—C1—C8 | 110.55 (11) | C13—C12—C11 | 120.06 (11) |
N1—C1—H1 | 124.7 | C13—C12—H12 | 120.0 |
C8—C1—H1 | 124.7 | C11—C12—H12 | 120.0 |
N1—C2—C3 | 129.31 (13) | C12—C13—C9 | 120.04 (11) |
N1—C2—C7 | 107.86 (12) | C12—C13—C21 | 117.84 (10) |
C3—C2—C7 | 122.83 (13) | C9—C13—C21 | 122.01 (11) |
C4—C3—C2 | 117.03 (15) | O1—C14—C15 | 120.48 (12) |
C4—C3—H3 | 121.5 | O1—C14—C11 | 117.25 (11) |
C2—C3—H3 | 121.5 | C15—C14—C11 | 122.26 (10) |
C3—C4—C5 | 121.22 (14) | C20—C15—C16 | 117.50 (12) |
C3—C4—H4 | 119.4 | C20—C15—C14 | 123.11 (12) |
C5—C4—H4 | 119.4 | C16—C15—C14 | 119.38 (11) |
C6—C5—C4 | 121.76 (15) | O2—C16—C17 | 117.64 (13) |
C6—C5—H5 | 119.1 | O2—C16—C15 | 122.20 (12) |
C4—C5—H5 | 119.1 | C17—C16—C15 | 120.16 (13) |
C5—C6—C7 | 118.83 (14) | C18—C17—C16 | 120.44 (15) |
C5—C6—H6 | 120.6 | C18—C17—H17 | 119.8 |
C7—C6—H6 | 120.6 | C16—C17—H17 | 119.8 |
C6—C7—C2 | 118.32 (12) | C17—C18—C19 | 120.77 (14) |
C6—C7—C8 | 135.38 (12) | C17—C18—H18 | 119.6 |
C2—C7—C8 | 106.30 (11) | C19—C18—H18 | 119.6 |
C1—C8—C9 | 128.49 (11) | C20—C19—C18 | 119.45 (14) |
C1—C8—C7 | 105.62 (11) | C20—C19—H19 | 120.3 |
C9—C8—C7 | 125.89 (11) | C18—C19—H19 | 120.3 |
N2—C9—C13 | 119.19 (11) | C19—C20—C15 | 121.61 (14) |
N2—C9—C8 | 116.18 (10) | C19—C20—H20 | 119.2 |
C13—C9—C8 | 124.56 (11) | C15—C20—H20 | 119.2 |
N2—C10—C11 | 125.62 (11) | N3—C21—C13 | 178.40 (14) |
N2—C10—H10 | 117.2 | C1—N1—C2 | 109.65 (11) |
C11—C10—H10 | 117.2 | C1—N1—H1A | 125.2 |
C12—C11—C10 | 115.75 (11) | C2—N1—H1A | 125.2 |
C12—C11—C14 | 125.71 (11) | C10—N2—C9 | 119.27 (10) |
C10—C11—C14 | 118.27 (11) | C16—O2—H2 | 109.5 |
N1—C2—C3—C4 | 178.70 (13) | C8—C9—C13—C12 | 178.66 (10) |
C7—C2—C3—C4 | −1.0 (2) | N2—C9—C13—C21 | −174.18 (10) |
C2—C3—C4—C5 | 1.0 (2) | C8—C9—C13—C21 | 2.61 (18) |
C3—C4—C5—C6 | −0.3 (3) | C12—C11—C14—O1 | 148.20 (13) |
C4—C5—C6—C7 | −0.5 (3) | C10—C11—C14—O1 | −25.54 (17) |
C5—C6—C7—C2 | 0.5 (2) | C12—C11—C14—C15 | −31.12 (18) |
C5—C6—C7—C8 | 179.75 (15) | C10—C11—C14—C15 | 155.15 (11) |
N1—C2—C7—C6 | −179.50 (11) | O1—C14—C15—C20 | 163.36 (13) |
C3—C2—C7—C6 | 0.29 (19) | C11—C14—C15—C20 | −17.35 (19) |
N1—C2—C7—C8 | 1.05 (13) | O1—C14—C15—C16 | −15.49 (19) |
C3—C2—C7—C8 | −179.16 (12) | C11—C14—C15—C16 | 163.80 (12) |
N1—C1—C8—C9 | −178.21 (11) | C20—C15—C16—O2 | −177.12 (13) |
N1—C1—C8—C7 | 1.71 (13) | C14—C15—C16—O2 | 1.8 (2) |
C6—C7—C8—C1 | 179.03 (14) | C20—C15—C16—C17 | 3.0 (2) |
C2—C7—C8—C1 | −1.66 (13) | C14—C15—C16—C17 | −178.12 (12) |
C6—C7—C8—C9 | −1.1 (2) | O2—C16—C17—C18 | 177.76 (15) |
C2—C7—C8—C9 | 178.26 (10) | C15—C16—C17—C18 | −2.3 (2) |
C1—C8—C9—N2 | −166.77 (11) | C16—C17—C18—C19 | 0.0 (3) |
C7—C8—C9—N2 | 13.34 (17) | C17—C18—C19—C20 | 1.7 (3) |
C1—C8—C9—C13 | 16.36 (19) | C18—C19—C20—C15 | −0.9 (2) |
C7—C8—C9—C13 | −163.54 (11) | C16—C15—C20—C19 | −1.3 (2) |
N2—C10—C11—C12 | 1.95 (18) | C14—C15—C20—C19 | 179.78 (13) |
N2—C10—C11—C14 | 176.31 (11) | C8—C1—N1—C2 | −1.10 (14) |
C10—C11—C12—C13 | −2.43 (16) | C3—C2—N1—C1 | −179.80 (13) |
C14—C11—C12—C13 | −176.31 (11) | C7—C2—N1—C1 | −0.02 (14) |
C11—C12—C13—C9 | 0.66 (17) | C11—C10—N2—C9 | 0.53 (18) |
C11—C12—C13—C21 | 176.88 (11) | C13—C9—N2—C10 | −2.44 (16) |
N2—C9—C13—C12 | 1.88 (16) | C8—C9—N2—C10 | −179.49 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3i | 0.86 | 2.15 | 3.0016 (17) | 171 |
O2—H2···O1 | 0.82 | 1.84 | 2.5653 (14) | 146 |
Symmetry code: (i) −x+1, y+1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3i | 0.86 | 2.15 | 3.0016 (17) | 171.2 |
O2—H2···O1 | 0.82 | 1.84 | 2.5653 (14) | 145.9 |
Symmetry code: (i) −x+1, y+1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H13N3O2 |
Mr | 339.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.4764 (6), 7.8471 (3), 16.7265 (8) |
β (°) | 90.478 (2) |
V (Å3) | 1637.53 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.28 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.969, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10911, 4105, 2665 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.121, 1.57 |
No. of reflections | 4105 |
No. of parameters | 237 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).
Footnotes
‡Emeritus Scientist.
Acknowledgements
The authors thank SAIF, IIT Madras, for providing the X-ray data collection facility.
References
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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.
Indole rings systems have become an important structural component in many pharmaceutical agents (Sundberg, 1996). Substituted indoles have been refered to as privileged structures since they are capable of binding to many receptors with high affinity (Evans et al., 1988). Some indole derivatives possess cytotoxic activity (Muratake et al., 1994). Indole and its bioisosters and derivatives have antimicrobial activity against Gram-negative and Gram-positive bacteria, the yeast Candida albicans and Enterobacter, Pseudomonas aeruginosa, E.coli, and Staphylococcus epidermidis (Biswal et al., 2012).
The structure of the title compound is shown in Figure 1. The C-N distances range from 1.345 (2) to 1.369 (2)Å, and are in good agreement with the related reported values (Vishnupriya et al., 2014). The bond distances C14-O1 and C21-N3 are 1.235 (1)Å and 1.141 (2)Å respectively, in agreement with values reported by (Vimala et al., 2015), confirming the presence of double and triple bonds. The pyridine ring (C9/N2/C10-C13) is in antiperiplanar(-ap) orientation with the indole ring (C1/N1/C2-C8)and in anti periplanar(+ap)orientation with the carbonyl bound hydroxy phenyl ring system (C15-C20) which are evidenced by the torsion angles (C7-C8-C9-C13 = -163.54 (1)°) and C10-C11-C14-C15 = 155.15 (1)°) respectively.
In the compound the intramolecular O-H···O hydrogen bond stabilizes the molecular structure while the intermolecular N-H···N hydrogen bonds between the indole NH and the cyanide nitrogen stabilize the crystal packing resulting to a two dimensional supra molecular network lying parallel to (011)plane.