organic compounds
(2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)hydrazinecarbothioamide
aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, bDepartment of Chemistry, Forman Christian College, Lahore 54600, Pakistan, and cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C16H13ClN4OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thiosemicarbazide and 2-chlorobenzyl groups, respectively. The near planarity of the isatin and thiosemicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intramolecular N—H⋯O and N—H⋯N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R22(8) loops. Aromatic π–π stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.
Related literature
For biochemical background to isatins, see: Pervez et al. (2012). For a related structure, see: Ramzan et al. (2010). For graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
10.1107/S1600536812035076/hb6928sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035076/hb6928Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035076/hb6928Isup3.cml
To a hot solution of isatin (0.74 g, 5 mmol) in 50% aqueous ethanol (15 ml) was added 4-(2-chlorobenzyl)thiosemicarbazide (1.08 g, 5 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then refluxed for 2 h. The orange crystalline solid formed during heating was collected by suction filtration. Thorough washing with hot aqueous ethanol afforded the title compound in pure form (1.55 g, 90%), m.p. 525 K. The orange prisms of title compound were grown from chloroform solution by slow evaporation of the solvent.
The H-atoms were positioned geometrically at C—H = 0.93 Å and N—H = 0.86 Å, respectively and included in the
as riding with U iso(H) = xUeq(C, N), where x = 1.2 for all H-atoms.Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted lines represent the intramolecular hydrogen bonds. Fig. 2. The partial packing diagram, which shows that molecules form dimers with R22(8) ring motifs. |
C16H13ClN4OS | F(000) = 712 |
Mr = 344.81 | Dx = 1.430 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2075 reflections |
a = 13.7017 (10) Å | θ = 1.5–28.4° |
b = 14.1585 (10) Å | µ = 0.38 mm−1 |
c = 8.2698 (5) Å | T = 296 K |
β = 93.151 (3)° | Prism, orange |
V = 1601.88 (19) Å3 | 0.32 × 0.23 × 0.20 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3935 independent reflections |
Radiation source: fine-focus sealed tube | 2541 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 7.50 pixels mm-1 | θmax = 28.4°, θmin = 1.5° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→18 |
Tmin = 0.888, Tmax = 0.929 | l = −8→11 |
14957 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.3273P] where P = (Fo2 + 2Fc2)/3 |
3935 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C16H13ClN4OS | V = 1601.88 (19) Å3 |
Mr = 344.81 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.7017 (10) Å | µ = 0.38 mm−1 |
b = 14.1585 (10) Å | T = 296 K |
c = 8.2698 (5) Å | 0.32 × 0.23 × 0.20 mm |
β = 93.151 (3)° |
Bruker Kappa APEXII CCD diffractometer | 3935 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2541 reflections with I > 2σ(I) |
Tmin = 0.888, Tmax = 0.929 | Rint = 0.033 |
14957 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.21 e Å−3 |
3935 reflections | Δρmin = −0.29 e Å−3 |
208 parameters |
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 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 | 0.34601 (5) | −0.04349 (4) | 0.12764 (8) | 0.0798 (3) | |
S1 | 0.30114 (4) | 0.37338 (4) | −0.01319 (6) | 0.0502 (2) | |
O1 | 0.07991 (10) | 0.44729 (9) | 0.35390 (16) | 0.0505 (5) | |
N1 | −0.05032 (11) | 0.37716 (11) | 0.47406 (17) | 0.0434 (5) | |
N2 | 0.11200 (10) | 0.24682 (10) | 0.24169 (15) | 0.0336 (4) | |
N3 | 0.17023 (10) | 0.31195 (10) | 0.17804 (16) | 0.0363 (5) | |
N4 | 0.26056 (11) | 0.19523 (11) | 0.06682 (17) | 0.0402 (5) | |
C1 | −0.02814 (12) | 0.22197 (12) | 0.40963 (19) | 0.0352 (5) | |
C2 | −0.04817 (15) | 0.12656 (14) | 0.4110 (2) | 0.0488 (7) | |
C3 | −0.12841 (17) | 0.09610 (16) | 0.4929 (3) | 0.0615 (8) | |
C4 | −0.18653 (16) | 0.16013 (18) | 0.5692 (3) | 0.0628 (8) | |
C5 | −0.16717 (15) | 0.25630 (16) | 0.5693 (2) | 0.0517 (7) | |
C6 | −0.08666 (13) | 0.28509 (13) | 0.48984 (19) | 0.0382 (6) | |
C7 | 0.02986 (13) | 0.37795 (13) | 0.3854 (2) | 0.0380 (6) | |
C8 | 0.04609 (12) | 0.27811 (12) | 0.33533 (18) | 0.0329 (5) | |
C9 | 0.24367 (12) | 0.28702 (12) | 0.07912 (19) | 0.0351 (5) | |
C10 | 0.34135 (14) | 0.15508 (15) | −0.0198 (2) | 0.0469 (7) | |
C11 | 0.42635 (14) | 0.12971 (14) | 0.0949 (2) | 0.0424 (6) | |
C12 | 0.43573 (15) | 0.04174 (14) | 0.1681 (2) | 0.0493 (7) | |
C13 | 0.51332 (19) | 0.01890 (19) | 0.2740 (3) | 0.0655 (9) | |
C14 | 0.5822 (2) | 0.0854 (2) | 0.3117 (3) | 0.0775 (10) | |
C15 | 0.57512 (18) | 0.1745 (2) | 0.2452 (3) | 0.0716 (10) | |
C16 | 0.49822 (16) | 0.19569 (16) | 0.1363 (3) | 0.0563 (8) | |
H1 | −0.07566 | 0.42658 | 0.51532 | 0.0520* | |
H2 | −0.00915 | 0.08379 | 0.35873 | 0.0585* | |
H3 | −0.14309 | 0.03203 | 0.49624 | 0.0737* | |
H3A | 0.16137 | 0.37063 | 0.19967 | 0.0436* | |
H4 | −0.24022 | 0.13810 | 0.62202 | 0.0754* | |
H4A | 0.22182 | 0.15693 | 0.11237 | 0.0482* | |
H5 | −0.20661 | 0.29916 | 0.62051 | 0.0620* | |
H10A | 0.36248 | 0.20052 | −0.09843 | 0.0563* | |
H10B | 0.31882 | 0.09901 | −0.07802 | 0.0563* | |
H13 | 0.51841 | −0.04121 | 0.31903 | 0.0786* | |
H14 | 0.63470 | 0.07069 | 0.38322 | 0.0930* | |
H15 | 0.62188 | 0.22004 | 0.27339 | 0.0861* | |
H16 | 0.49455 | 0.25549 | 0.08983 | 0.0676* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0945 (5) | 0.0626 (4) | 0.0842 (4) | −0.0105 (3) | 0.0230 (4) | 0.0024 (3) |
S1 | 0.0545 (3) | 0.0484 (3) | 0.0491 (3) | −0.0073 (3) | 0.0144 (2) | 0.0011 (2) |
O1 | 0.0604 (9) | 0.0332 (7) | 0.0602 (8) | −0.0045 (7) | 0.0230 (7) | −0.0027 (6) |
N1 | 0.0451 (10) | 0.0386 (9) | 0.0477 (9) | 0.0048 (7) | 0.0148 (7) | −0.0051 (7) |
N2 | 0.0338 (8) | 0.0342 (8) | 0.0326 (7) | 0.0000 (7) | −0.0002 (6) | −0.0001 (6) |
N3 | 0.0378 (9) | 0.0321 (8) | 0.0396 (8) | 0.0006 (7) | 0.0073 (7) | −0.0032 (6) |
N4 | 0.0364 (9) | 0.0423 (9) | 0.0424 (8) | 0.0042 (7) | 0.0080 (7) | 0.0018 (7) |
C1 | 0.0363 (10) | 0.0384 (10) | 0.0304 (8) | −0.0040 (8) | −0.0014 (7) | −0.0002 (7) |
C2 | 0.0574 (13) | 0.0422 (11) | 0.0466 (11) | −0.0061 (10) | 0.0023 (9) | −0.0018 (9) |
C3 | 0.0712 (16) | 0.0534 (13) | 0.0598 (13) | −0.0266 (12) | 0.0038 (12) | 0.0019 (11) |
C4 | 0.0571 (14) | 0.0799 (17) | 0.0526 (12) | −0.0262 (13) | 0.0135 (11) | 0.0042 (12) |
C5 | 0.0434 (12) | 0.0663 (14) | 0.0460 (11) | −0.0069 (11) | 0.0091 (9) | −0.0059 (10) |
C6 | 0.0381 (11) | 0.0440 (10) | 0.0323 (9) | −0.0036 (9) | 0.0007 (8) | −0.0011 (8) |
C7 | 0.0415 (11) | 0.0363 (10) | 0.0366 (9) | 0.0018 (9) | 0.0057 (8) | −0.0005 (7) |
C8 | 0.0350 (10) | 0.0340 (9) | 0.0295 (8) | 0.0011 (8) | −0.0010 (7) | −0.0008 (7) |
C9 | 0.0343 (10) | 0.0420 (10) | 0.0287 (8) | 0.0015 (8) | −0.0015 (7) | −0.0040 (7) |
C10 | 0.0504 (12) | 0.0531 (12) | 0.0376 (10) | 0.0165 (10) | 0.0065 (9) | −0.0019 (9) |
C11 | 0.0421 (12) | 0.0499 (11) | 0.0364 (9) | 0.0132 (10) | 0.0121 (8) | −0.0004 (8) |
C12 | 0.0519 (13) | 0.0535 (12) | 0.0439 (11) | 0.0106 (10) | 0.0159 (10) | −0.0010 (9) |
C13 | 0.0745 (17) | 0.0705 (16) | 0.0519 (13) | 0.0304 (15) | 0.0065 (12) | 0.0110 (11) |
C14 | 0.0614 (17) | 0.103 (2) | 0.0668 (16) | 0.0278 (17) | −0.0094 (13) | −0.0021 (15) |
C15 | 0.0481 (14) | 0.090 (2) | 0.0766 (16) | 0.0000 (14) | 0.0015 (12) | −0.0178 (15) |
C16 | 0.0509 (14) | 0.0575 (14) | 0.0615 (13) | 0.0094 (12) | 0.0111 (11) | 0.0021 (10) |
Cl1—C12 | 1.742 (2) | C5—C6 | 1.376 (3) |
S1—C9 | 1.6625 (18) | C7—C8 | 1.493 (2) |
O1—C7 | 1.234 (2) | C10—C11 | 1.505 (3) |
N1—C6 | 1.404 (2) | C11—C16 | 1.387 (3) |
N1—C7 | 1.354 (2) | C11—C12 | 1.388 (3) |
N2—N3 | 1.345 (2) | C12—C13 | 1.378 (3) |
N2—C8 | 1.299 (2) | C13—C14 | 1.357 (4) |
N3—C9 | 1.377 (2) | C14—C15 | 1.378 (4) |
N4—C9 | 1.325 (2) | C15—C16 | 1.381 (3) |
N4—C10 | 1.466 (2) | C2—H2 | 0.9300 |
N1—H1 | 0.8600 | C3—H3 | 0.9300 |
N3—H3A | 0.8600 | C4—H4 | 0.9300 |
N4—H4A | 0.8600 | C5—H5 | 0.9300 |
C1—C8 | 1.453 (2) | C10—H10A | 0.9700 |
C1—C2 | 1.379 (3) | C10—H10B | 0.9700 |
C1—C6 | 1.393 (2) | C13—H13 | 0.9300 |
C2—C3 | 1.391 (3) | C14—H14 | 0.9300 |
C3—C4 | 1.382 (3) | C15—H15 | 0.9300 |
C4—C5 | 1.387 (3) | C16—H16 | 0.9300 |
C6—N1—C7 | 111.13 (15) | C10—C11—C16 | 120.63 (18) |
N3—N2—C8 | 116.49 (14) | C10—C11—C12 | 122.63 (18) |
N2—N3—C9 | 121.67 (14) | C11—C12—C13 | 122.5 (2) |
C9—N4—C10 | 123.90 (15) | Cl1—C12—C11 | 119.38 (15) |
C7—N1—H1 | 124.00 | Cl1—C12—C13 | 118.11 (17) |
C6—N1—H1 | 124.00 | C12—C13—C14 | 119.1 (2) |
C9—N3—H3A | 119.00 | C13—C14—C15 | 120.7 (2) |
N2—N3—H3A | 119.00 | C14—C15—C16 | 119.6 (2) |
C9—N4—H4A | 118.00 | C11—C16—C15 | 121.4 (2) |
C10—N4—H4A | 118.00 | C1—C2—H2 | 121.00 |
C2—C1—C6 | 120.31 (16) | C3—C2—H2 | 121.00 |
C2—C1—C8 | 133.12 (16) | C2—C3—H3 | 120.00 |
C6—C1—C8 | 106.56 (15) | C4—C3—H3 | 120.00 |
C1—C2—C3 | 118.08 (18) | C3—C4—H4 | 119.00 |
C2—C3—C4 | 120.6 (2) | C5—C4—H4 | 119.00 |
C3—C4—C5 | 122.0 (2) | C4—C5—H5 | 122.00 |
C4—C5—C6 | 116.66 (19) | C6—C5—H5 | 122.00 |
N1—C6—C1 | 109.58 (15) | N4—C10—H10A | 109.00 |
N1—C6—C5 | 128.09 (17) | N4—C10—H10B | 109.00 |
C1—C6—C5 | 122.33 (18) | C11—C10—H10A | 109.00 |
O1—C7—N1 | 126.73 (17) | C11—C10—H10B | 109.00 |
O1—C7—C8 | 127.01 (16) | H10A—C10—H10B | 108.00 |
N1—C7—C8 | 106.26 (15) | C12—C13—H13 | 120.00 |
N2—C8—C7 | 127.38 (15) | C14—C13—H13 | 120.00 |
N2—C8—C1 | 126.22 (16) | C13—C14—H14 | 120.00 |
C1—C8—C7 | 106.39 (14) | C15—C14—H14 | 120.00 |
S1—C9—N3 | 117.66 (13) | C14—C15—H15 | 120.00 |
S1—C9—N4 | 126.66 (13) | C16—C15—H15 | 120.00 |
N3—C9—N4 | 115.68 (15) | C11—C16—H16 | 119.00 |
N4—C10—C11 | 111.33 (14) | C15—C16—H16 | 119.00 |
C12—C11—C16 | 116.71 (18) | ||
C7—N1—C6—C1 | 0.42 (19) | C1—C2—C3—C4 | 0.6 (3) |
C7—N1—C6—C5 | −179.26 (17) | C2—C3—C4—C5 | −0.8 (4) |
C6—N1—C7—O1 | −177.87 (17) | C3—C4—C5—C6 | −0.2 (3) |
C6—N1—C7—C8 | 1.46 (18) | C4—C5—C6—N1 | −178.93 (18) |
C8—N2—N3—C9 | 178.97 (14) | C4—C5—C6—C1 | 1.4 (3) |
N3—N2—C8—C1 | 176.21 (14) | O1—C7—C8—N2 | −4.5 (3) |
N3—N2—C8—C7 | −2.4 (2) | O1—C7—C8—C1 | 176.61 (17) |
N2—N3—C9—S1 | 171.76 (11) | N1—C7—C8—N2 | 176.14 (16) |
N2—N3—C9—N4 | −7.8 (2) | N1—C7—C8—C1 | −2.73 (18) |
C10—N4—C9—S1 | 6.5 (2) | N4—C10—C11—C12 | 89.5 (2) |
C10—N4—C9—N3 | −174.00 (14) | N4—C10—C11—C16 | −88.4 (2) |
C9—N4—C10—C11 | 98.6 (2) | C10—C11—C12—Cl1 | −0.3 (2) |
C6—C1—C2—C3 | 0.6 (3) | C10—C11—C12—C13 | −179.54 (19) |
C8—C1—C2—C3 | −178.34 (19) | C16—C11—C12—Cl1 | 177.75 (15) |
C2—C1—C6—N1 | 178.63 (15) | C16—C11—C12—C13 | −1.5 (3) |
C2—C1—C6—C5 | −1.7 (3) | C10—C11—C16—C15 | 178.0 (2) |
C8—C1—C6—N1 | −2.16 (18) | C12—C11—C16—C15 | −0.1 (3) |
C8—C1—C6—C5 | 177.54 (16) | Cl1—C12—C13—C14 | −177.65 (19) |
C2—C1—C8—N2 | 3.1 (3) | C11—C12—C13—C14 | 1.7 (3) |
C2—C1—C8—C7 | −177.98 (18) | C12—C13—C14—C15 | −0.1 (4) |
C6—C1—C8—N2 | −175.93 (15) | C13—C14—C15—C16 | −1.4 (4) |
C6—C1—C8—C7 | 2.96 (17) | C14—C15—C16—C11 | 1.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1 | 0.86 | 2.05 | 2.7416 (19) | 137 |
N4—H4A···N2 | 0.86 | 2.28 | 2.663 (2) | 107 |
N1—H1···O1i | 0.86 | 2.09 | 2.903 (2) | 157 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H13ClN4OS |
Mr | 344.81 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.7017 (10), 14.1585 (10), 8.2698 (5) |
β (°) | 93.151 (3) |
V (Å3) | 1601.88 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.38 |
Crystal size (mm) | 0.32 × 0.23 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.888, 0.929 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14957, 3935, 2541 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.105, 1.02 |
No. of reflections | 3935 |
No. of parameters | 208 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.29 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1 | 0.86 | 2.05 | 2.7416 (19) | 137 |
N4—H4A···N2 | 0.86 | 2.28 | 2.663 (2) | 107 |
N1—H1···O1i | 0.86 | 2.09 | 2.903 (2) | 157 |
Symmetry code: (i) −x, −y+1, −z+1. |
Acknowledgements
HP, MSI and NK thank the Higher Education Commission (HEC), Pakistan, for financial assistance under the National Research Program for Universities (project No. 20–873/R&D/07/452).
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As a part of our ongoing work on the synthesis of isatin-thiosemicarbazones having certain pharmaceutical applications (Pervez et al., 2012), we report herein the synthesis and crystal structure of the title compound (Fig. 1). The crystal structure of 1-(2-oxoindolin-3-ylidene)-4-[2-(trifluoromethoxy)phenyl]thiosemicarbazide (Ramzan et al. 2010) has been published which is related to the title compound.
In the title compound, the group A (C1—C8/N1/O1) of isatin moiety, group B (N2/N3/C9/S1/N4) of thiosemicarbazide and group C (C10—C16/CL1) of 2-chlorobenzyl are planar with r.m.s. deviations of 0.0230 Å, 0.0420 Å and 0.0163 Å, respectively. The dihedral angle between A/B, A/C and B/C are 10.60 (7)°, 72.60 (3)° and 72.89 (3)°, respectively. In the title compound, S(5) and S(6) ring motifs (Bernstein et al., 1995) are formed due to intramolecular H-bondings of N—H···N and N—H···O types, respectively (Table 1, Fig. 1). The molecules are stabilized in the form of dimers due to H-bonding of N—H···O type (Table 1, Fig. 2) with R22(8) ring motif. There exists π–π interaction between Cg1···Cg2i [i = x, 1/2 - y, -1/2 + z] at a distance of 3.6866 (11) Å, where Cg1 and Cg2 are the centroids of heterocyclic five membered ring (C1/C6/N1/C7/C8) and the benzene ring (C1—C6), respectively. Similarly, π–π interaction exists between Cg2···Cg1ii [ii = x, 1/2 - y, 1/2 + z] at a distance of 3.6866 (11) Å.