organic compounds
4-Chloro-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]benzohydrazide
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eChemistry Department, Faculty of Science, Assiut University, Assiut, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C15H10ClN3O2, the benzene ring is slightly twisted out of the plane of the 2,3-dihydro-1H-indole ring system (r.m.s. deviation = 0.007 Å), forming a dihedral angle of 7.4 (3)°. An intramolecular N—H⋯O hydrogen bond forms a six-membered ring. In the crystal, molecules are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming layers alternately perpendicular to [011] and [0-11].
CCDC reference: 975733
Related literature
For the diverse bio-activities of acid et al. (2012); Al-Assar et al. (2002); Dharmaraj et al. (2001); Jain & Vederas (2004); Jeeworth et al. (2000); Scozzafava et al. (2001); Siddappa et al. (2008); Strappaghetti et al. (2006).
and their condensed products, see: AdekunleExperimental
Crystal data
|
Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; 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: PLATON (Spek, 2009).
Supporting information
CCDC reference: 975733
https://doi.org/10.1107/S1600536813033345/su2672sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033345/su2672Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033345/su2672Isup3.cml
A mixture of 1 mmol (170.6 mg) 4-chlorobenzohydrazidean and 1 mmol (147 mg) 1H-indole-2,3-dione in 25 ml ethanol with few drops of glacial acetic acid was refluxed for 5h. The solid formed was collected and recrystallized from DMF to furnish the title compound as yellow crystals suitable for X-ray analysis [M.p. 558 K].
The NH H atoms (H1 on N1) was located in a difference Fourier map and refined with a distance restraint: N1—H1 = 0.90 (5) Å with Uiso(H) = 1.2Ueq(N). The remaining H atoms were placed in calculated positions and refined using a riding model approximation: C—H = 0.95 Å and N—H = 0.91 Å with Uiso(H) = 1.2Ueq(C, N). The small proportion of reflections observed is a result of the rather poor quality of the very thin crystals obtained.
Hydrazide compounds and their condensation products exhibit a wide range of biological activities such as anti-cancer (Strappaghetti et al., 2006), anti-depressant (Al-Assar et al., 2002), anti-HIV (Adekunle et al., 2012), analgesic-anti-inflammatory (Jain & Vederas, 2004), bactericidal (Jeeworth et al., 2000), leishmanicidal (Scozzafava et al., 2001), anti-helmintic (Dharmaraj et al., 2001) and anti-tuberculosis activities (Siddappa et al., 2008). Based on such findings and continuing to our on-going study of the synthesis of bio-active
we herein report on the synthesis and of the title compound.In the title compound, Fig. 1, the intramolecular N1—H1···O2 hydrogen bond forms a pseudo-six-membered ring. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.007 Å). The benzene ring and the 2,3-dihydro-1H-indole ring system make a dihedral angle of 7.4 (3)° .
In the
molecular layers formed by N—H···O and C-H···O hydrogen bonds are alternately perpendicular to [011] and to [0–11] directions (Table 1 and Fig. 2).For the diverse bio-activities of acid
and their condensed products, see: Adekunle et al. (2012); Al-Assar et al. (2002); Dharmaraj et al. (2001); Jain & Vederas (2004); Jeeworth et al. (2000); Scozzafava et al. (2001); Siddappa et al. (2008); Strappaghetti et al. (2006).Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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: PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular N-H···O hydrogen bond is shown as a dashed line (see Table 1 for details). | |
Fig. 2. A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as a dashed lines (see Table 1 for details). |
C15H10ClN3O2 | F(000) = 616 |
Mr = 299.71 | Dx = 1.550 Mg m−3 |
Orthorhombic, Pca21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3290 reflections |
a = 31.0359 (12) Å | θ = 2.9–68.5° |
b = 5.2549 (3) Å | µ = 2.72 mm−1 |
c = 7.8730 (4) Å | T = 102 K |
V = 1284.01 (11) Å3 | Plate, yellow |
Z = 4 | 0.22 × 0.17 × 0.01 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 1596 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 1434 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.109 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 68.5°, θmin = 5.7° |
ω scans | h = −32→37 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −5→5 |
Tmin = 0.75, Tmax = 0.97 | l = −8→9 |
4190 measured reflections |
Refinement on F2 | Secondary atom site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.059 | W = 1/[Σ2(Fo2) + (0.0459P)2 + 3.7436P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.152 | (Δ/σ)max < 0.001 |
S = 1.16 | Δρmax = 0.30 e Å−3 |
1596 reflections | Δρmin = −0.37 e Å−3 |
193 parameters | Absolute structure: Flack (1983), 478 Friedal pairs (44% coverage) |
3 restraints | Absolute structure parameter: −0.06 (5) |
Primary atom site location: difference Fourier map |
C15H10ClN3O2 | V = 1284.01 (11) Å3 |
Mr = 299.71 | Z = 4 |
Orthorhombic, Pca21 | Cu Kα radiation |
a = 31.0359 (12) Å | µ = 2.72 mm−1 |
b = 5.2549 (3) Å | T = 102 K |
c = 7.8730 (4) Å | 0.22 × 0.17 × 0.01 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 1596 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 1434 reflections with I > 2σ(I) |
Tmin = 0.75, Tmax = 0.97 | Rint = 0.109 |
4190 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.152 | Δρmax = 0.30 e Å−3 |
S = 1.16 | Δρmin = −0.37 e Å−3 |
1596 reflections | Absolute structure: Flack (1983), 478 Friedal pairs (44% coverage) |
193 parameters | Absolute structure parameter: −0.06 (5) |
3 restraints |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | −0.02432 (5) | 0.0784 (4) | 0.5130 (3) | 0.0317 (6) | |
O1 | 0.15220 (15) | 0.7554 (12) | 0.7066 (7) | 0.0247 (19) | |
O2 | 0.21783 (16) | 0.0289 (11) | 0.3951 (7) | 0.0240 (19) | |
N1 | 0.18451 (17) | 0.4151 (14) | 0.5756 (8) | 0.0187 (19) | |
N2 | 0.22478 (17) | 0.5046 (12) | 0.6135 (8) | 0.0173 (19) | |
N3 | 0.29242 (19) | 0.0513 (13) | 0.4056 (8) | 0.0203 (19) | |
C1 | 0.0263 (2) | 0.2224 (17) | 0.5393 (10) | 0.026 (3) | |
C2 | 0.0616 (2) | 0.1072 (16) | 0.4604 (10) | 0.023 (2) | |
C3 | 0.1021 (2) | 0.2172 (17) | 0.4862 (10) | 0.026 (3) | |
C4 | 0.1069 (2) | 0.4273 (16) | 0.5882 (9) | 0.020 (2) | |
C5 | 0.0705 (2) | 0.5395 (17) | 0.6625 (10) | 0.026 (3) | |
C6 | 0.0301 (2) | 0.4340 (18) | 0.6391 (11) | 0.028 (3) | |
C7 | 0.1495 (2) | 0.5554 (18) | 0.6291 (10) | 0.024 (3) | |
C8 | 0.2560 (2) | 0.3623 (15) | 0.5494 (9) | 0.018 (2) | |
C9 | 0.2517 (2) | 0.1344 (16) | 0.4425 (10) | 0.022 (2) | |
C10 | 0.3234 (2) | 0.2196 (15) | 0.4808 (9) | 0.018 (2) | |
C11 | 0.3677 (2) | 0.2028 (16) | 0.4744 (10) | 0.022 (2) | |
C12 | 0.3910 (2) | 0.3895 (16) | 0.5590 (10) | 0.025 (3) | |
C13 | 0.3700 (2) | 0.5837 (17) | 0.6480 (10) | 0.025 (3) | |
C14 | 0.3253 (2) | 0.5978 (15) | 0.6566 (9) | 0.019 (3) | |
C15 | 0.3018 (2) | 0.4074 (16) | 0.5723 (9) | 0.021 (3) | |
H1 | 0.1866 (10) | 0.264 (9) | 0.523 (10) | 0.0220* | |
H2 | 0.05820 | −0.04030 | 0.39190 | 0.0280* | |
H3 | 0.12660 | 0.14550 | 0.43240 | 0.0310* | |
H3A | 0.30090 | −0.06130 | 0.32440 | 0.0250* | |
H5 | 0.07370 | 0.68880 | 0.72940 | 0.0320* | |
H6 | 0.00550 | 0.50730 | 0.69140 | 0.0340* | |
H11 | 0.38160 | 0.06920 | 0.41470 | 0.0270* | |
H12 | 0.42160 | 0.38530 | 0.55640 | 0.0290* | |
H13 | 0.38670 | 0.70950 | 0.70410 | 0.0300* | |
H14 | 0.31130 | 0.73060 | 0.71710 | 0.0230* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0189 (8) | 0.0414 (13) | 0.0349 (11) | −0.0052 (7) | −0.0031 (9) | 0.0024 (11) |
O1 | 0.022 (3) | 0.030 (4) | 0.022 (3) | 0.004 (2) | −0.001 (2) | −0.009 (3) |
O2 | 0.023 (3) | 0.030 (4) | 0.019 (3) | −0.002 (2) | −0.001 (2) | −0.007 (3) |
N1 | 0.015 (3) | 0.024 (4) | 0.017 (3) | 0.003 (2) | −0.002 (2) | −0.006 (3) |
N2 | 0.019 (3) | 0.021 (4) | 0.012 (3) | 0.000 (2) | 0.002 (2) | 0.000 (3) |
N3 | 0.020 (3) | 0.024 (4) | 0.017 (3) | 0.001 (3) | −0.001 (3) | −0.007 (3) |
C1 | 0.020 (3) | 0.040 (6) | 0.019 (4) | −0.006 (3) | −0.008 (3) | 0.009 (4) |
C2 | 0.023 (3) | 0.023 (5) | 0.024 (4) | −0.003 (3) | −0.004 (3) | −0.006 (4) |
C3 | 0.026 (4) | 0.033 (5) | 0.019 (4) | −0.001 (3) | −0.002 (4) | −0.005 (4) |
C4 | 0.025 (4) | 0.025 (5) | 0.010 (3) | −0.004 (3) | −0.003 (3) | 0.002 (3) |
C5 | 0.022 (4) | 0.039 (6) | 0.018 (4) | 0.003 (3) | 0.001 (3) | −0.005 (4) |
C6 | 0.021 (4) | 0.040 (6) | 0.023 (4) | 0.007 (3) | 0.005 (3) | −0.001 (4) |
C7 | 0.022 (4) | 0.036 (6) | 0.015 (4) | 0.006 (3) | 0.001 (3) | 0.003 (4) |
C8 | 0.025 (3) | 0.019 (5) | 0.009 (4) | 0.002 (3) | 0.005 (3) | 0.002 (3) |
C9 | 0.013 (3) | 0.038 (5) | 0.016 (4) | 0.001 (3) | −0.002 (3) | 0.005 (4) |
C10 | 0.017 (3) | 0.025 (5) | 0.013 (4) | 0.000 (3) | −0.003 (3) | −0.004 (3) |
C11 | 0.025 (3) | 0.022 (5) | 0.020 (4) | 0.006 (3) | 0.000 (3) | 0.004 (4) |
C12 | 0.017 (3) | 0.034 (6) | 0.023 (5) | 0.002 (3) | 0.000 (3) | 0.003 (4) |
C13 | 0.022 (4) | 0.034 (6) | 0.018 (4) | −0.001 (3) | −0.001 (3) | 0.001 (4) |
C14 | 0.026 (4) | 0.016 (5) | 0.016 (4) | 0.000 (3) | −0.001 (3) | 0.001 (3) |
C15 | 0.024 (4) | 0.022 (5) | 0.018 (4) | 0.002 (3) | −0.001 (3) | −0.001 (3) |
Cl1—C1 | 1.756 (7) | C8—C9 | 1.470 (11) |
O1—C7 | 1.218 (11) | C8—C15 | 1.452 (9) |
O2—C9 | 1.246 (9) | C10—C15 | 1.394 (11) |
N1—N2 | 1.368 (8) | C10—C11 | 1.379 (9) |
N1—C7 | 1.379 (10) | C11—C12 | 1.389 (11) |
N2—C8 | 1.324 (9) | C12—C13 | 1.399 (11) |
N3—C9 | 1.368 (9) | C13—C14 | 1.391 (9) |
N3—C10 | 1.434 (9) | C14—C15 | 1.405 (11) |
N1—H1 | 0.90 (5) | C2—H2 | 0.9500 |
N3—H3A | 0.9100 | C3—H3 | 0.9500 |
C1—C6 | 1.367 (13) | C5—H5 | 0.9500 |
C1—C2 | 1.397 (10) | C6—H6 | 0.9500 |
C2—C3 | 1.398 (10) | C11—H11 | 0.9500 |
C3—C4 | 1.373 (12) | C12—H12 | 0.9500 |
C4—C5 | 1.402 (10) | C13—H13 | 0.9500 |
C4—C7 | 1.518 (10) | C14—H14 | 0.9500 |
C5—C6 | 1.383 (10) | ||
N2—N1—C7 | 118.0 (7) | N3—C10—C15 | 109.1 (6) |
N1—N2—C8 | 113.0 (6) | C11—C10—C15 | 123.0 (7) |
C9—N3—C10 | 109.6 (6) | N3—C10—C11 | 127.9 (7) |
C7—N1—H1 | 132 (2) | C10—C11—C12 | 117.2 (7) |
N2—N1—H1 | 110 (2) | C11—C12—C13 | 120.9 (6) |
C9—N3—H3A | 129.00 | C12—C13—C14 | 121.9 (7) |
C10—N3—H3A | 120.00 | C13—C14—C15 | 117.2 (7) |
Cl1—C1—C6 | 119.7 (5) | C8—C15—C14 | 133.1 (7) |
C2—C1—C6 | 122.7 (6) | C10—C15—C14 | 119.9 (6) |
Cl1—C1—C2 | 117.5 (6) | C8—C15—C10 | 106.9 (6) |
C1—C2—C3 | 117.5 (7) | C1—C2—H2 | 121.00 |
C2—C3—C4 | 121.0 (7) | C3—C2—H2 | 121.00 |
C3—C4—C5 | 119.6 (6) | C2—C3—H3 | 119.00 |
C3—C4—C7 | 125.1 (6) | C4—C3—H3 | 120.00 |
C5—C4—C7 | 115.3 (7) | C4—C5—H5 | 120.00 |
C4—C5—C6 | 120.4 (8) | C6—C5—H5 | 120.00 |
C1—C6—C5 | 118.7 (7) | C1—C6—H6 | 121.00 |
O1—C7—C4 | 123.3 (6) | C5—C6—H6 | 121.00 |
N1—C7—C4 | 112.6 (7) | C10—C11—H11 | 121.00 |
O1—C7—N1 | 124.1 (6) | C12—C11—H11 | 122.00 |
N2—C8—C9 | 127.7 (6) | C11—C12—H12 | 120.00 |
N2—C8—C15 | 125.2 (7) | C13—C12—H12 | 120.00 |
C9—C8—C15 | 107.0 (6) | C12—C13—H13 | 119.00 |
N3—C9—C8 | 107.3 (6) | C14—C13—H13 | 119.00 |
O2—C9—N3 | 125.0 (7) | C13—C14—H14 | 121.00 |
O2—C9—C8 | 127.7 (6) | C15—C14—H14 | 122.00 |
C7—N1—N2—C8 | −177.0 (7) | C5—C4—C7—N1 | 170.3 (7) |
N2—N1—C7—O1 | 0.7 (12) | C4—C5—C6—C1 | −1.5 (13) |
N2—N1—C7—C4 | −176.6 (6) | N2—C8—C9—O2 | −1.7 (14) |
N1—N2—C8—C9 | 2.1 (11) | N2—C8—C9—N3 | 179.7 (7) |
N1—N2—C8—C15 | −178.5 (7) | C15—C8—C9—O2 | 178.8 (8) |
C10—N3—C9—O2 | 179.9 (7) | C15—C8—C9—N3 | 0.1 (8) |
C10—N3—C9—C8 | −1.4 (8) | N2—C8—C15—C10 | −178.3 (7) |
C9—N3—C10—C11 | 179.7 (8) | N2—C8—C15—C14 | −1.6 (14) |
C9—N3—C10—C15 | 2.2 (9) | C9—C8—C15—C10 | 1.2 (8) |
Cl1—C1—C2—C3 | −177.9 (6) | C9—C8—C15—C14 | 177.9 (8) |
C6—C1—C2—C3 | −0.2 (12) | N3—C10—C11—C12 | −179.6 (7) |
Cl1—C1—C6—C5 | 177.9 (7) | C15—C10—C11—C12 | −2.4 (12) |
C2—C1—C6—C5 | 0.3 (13) | N3—C10—C15—C8 | −2.1 (8) |
C1—C2—C3—C4 | 1.3 (12) | N3—C10—C15—C14 | −179.3 (7) |
C2—C3—C4—C5 | −2.5 (12) | C11—C10—C15—C8 | −179.7 (7) |
C2—C3—C4—C7 | 177.8 (8) | C11—C10—C15—C14 | 3.1 (12) |
C3—C4—C5—C6 | 2.6 (12) | C10—C11—C12—C13 | 0.7 (12) |
C7—C4—C5—C6 | −177.7 (8) | C11—C12—C13—C14 | 0.4 (12) |
C3—C4—C7—O1 | 172.7 (8) | C12—C13—C14—C15 | 0.2 (12) |
C3—C4—C7—N1 | −10.0 (11) | C13—C14—C15—C8 | −178.2 (8) |
C5—C4—C7—O1 | −7.0 (12) | C13—C14—C15—C10 | −1.9 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.90 (5) | 1.87 (6) | 2.685 (9) | 151 (4) |
N3—H3A···O1i | 0.91 | 1.98 | 2.798 (8) | 149 |
C11—H11···O1i | 0.95 | 2.55 | 3.218 (10) | 128 |
C14—H14···O2ii | 0.95 | 2.29 | 3.233 (9) | 172 |
Symmetry codes: (i) −x+1/2, y−1, z−1/2; (ii) −x+1/2, y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.90 (5) | 1.87 (6) | 2.685 (9) | 151 (4) |
N3—H3A···O1i | 0.91 | 1.98 | 2.798 (8) | 149 |
C11—H11···O1i | 0.95 | 2.55 | 3.218 (10) | 128 |
C14—H14···O2ii | 0.95 | 2.29 | 3.233 (9) | 172 |
Symmetry codes: (i) −x+1/2, y−1, z−1/2; (ii) −x+1/2, y+1, z+1/2. |
Acknowledgements
Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study. The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer is also gratefully acknowledged.
References
Adekunle, F. A. O., Woods, J. A. O. & Odunola, O. A. (2012). Res. J. Pharm. Bio. Chem. Sci., 3, 1120-1127. CAS Google Scholar
Al-Assar, F., Zelenin, K. N., Lesiovskaya, E. E., Bezant, I. P. & Chakchir, B. A. (2002). Pharm. Chem. J. 36, 598–603. CAS Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dharmaraj, N., Viswanalhamurthi, P. & Natarajan, K. (2001). Transition Met. Chem. 26, 105–118. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jain, R. P. & Vederas, J. C. (2004). Bioorg. Med. Chem. Lett. 14, 3655–3658. Web of Science CrossRef PubMed CAS Google Scholar
Jeeworth, T., Wah, H. L. K., Bhowon, M. G., Ghoorhoo, D. & Babooram, K. (2000). Synth. React. Inorg. Met. Org. Chem. 30, 1023–1038. Google Scholar
Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G. & Supuran, C. T. (2001). Bioorg. Med. Chem. Lett. 11, 575–582. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddappa, K., Reddy, T., Mallikarjun, M. & Reddy, C. V. (2008). Eur. J. Chem. 5, 155–162. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Strappaghetti, G., Brodi, C., Giannaccini, G. & Betti, L. (2006). Bioorg. Med. Chem. Lett. 16, 2575–2579. Web of Science CrossRef PubMed CAS Google Scholar
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Hydrazide compounds and their condensation products exhibit a wide range of biological activities such as anti-cancer (Strappaghetti et al., 2006), anti-depressant (Al-Assar et al., 2002), anti-HIV (Adekunle et al., 2012), analgesic-anti-inflammatory (Jain & Vederas, 2004), bactericidal (Jeeworth et al., 2000), leishmanicidal (Scozzafava et al., 2001), anti-helmintic (Dharmaraj et al., 2001) and anti-tuberculosis activities (Siddappa et al., 2008). Based on such findings and continuing to our on-going study of the synthesis of bio-active heterocyclic compounds, we herein report on the synthesis and crystal structure of the title compound.
In the title compound, Fig. 1, the intramolecular N1—H1···O2 hydrogen bond forms a pseudo-six-membered ring. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.007 Å). The benzene ring and the 2,3-dihydro-1H-indole ring system make a dihedral angle of 7.4 (3)° .
In the crystal structure, molecular layers formed by N—H···O and C-H···O hydrogen bonds are alternately perpendicular to [011] and to [0–11] directions (Table 1 and Fig. 2).