organic compounds
(Z)-2-(5-Methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide
aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia, bFaculty of Science, Sabha University, Libya, cDepartment of Chemistry, International University of Africa, Khartoum, Sudan, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: sgteoh@usm.my
In the title compound, C16H14N4OS, the dihedral angle between the nine-membered 5-methylindolin-2-one ring system and the benzene ring is 10.21 (7)°. Intramolecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding interactions [graph set S(6)] are present within the N—N—C—N chain between the ring systems. In the crystal, molecules form centrosymmetric cyclic dimers through pairs of N—H⋯O hydrogen bonds [graph set R22(8)].
Related literature
For related structures, see: Qasem Ali et al. (2011); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For the biological activity of see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For the cytotoxic and anticancer activiy of isatin and its derivatives, see: Vine et al. (2009). For bond-length data, see; Allen et al. (1987). For graph-set analysis, see Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536811049154/zs2160sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049154/zs2160Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811049154/zs2160Isup3.cml
The title compound was synthesized by refluxing the reaction mixture of 4-phenyl-3-thiosemicarbazide (0.01 mol) and 5-methylisatin (0.01 mol) in 60 ml of ethanol for 2 hrs. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH: yield 80%. The orange crystals (m.p. 511.8–512.3 K) were grown in acetone-DMF (3:1) by slow evaporation at room temperature.
H atoms bound to N were located in a difference-Fourier map and were refined freely. The remaining H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å (aryl) and 0.98 Å (methyl) and Uiso(H) = 1.2Ueq(aryl C) and Uiso(H) = 1.5Ueq(methyl C). The highest residual electron density peak (0.397 eÅ-3)is located at 0.71 Å from C8 and the deepest hole (-0.303 eÅ-3) is located at 1.33 Å from C6.
Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. Biological properties of isatin and its derivatives include a range of actions in the brain and offer protection against certain types of infections, such as antibacterial (Suryavanshi & Pai, 2006) antifungal, anticonvulsant, anti-HIV (Pandeya et al., 1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the
of (Z)-2-(5-chloro-2- oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (Qasem Ali et al., 2011). In the present paper we describe the single-crystal X-ray diffraction study of title compound, C16H14N4OS.In this compound (Fig. 1), the dihedral angle between the nine-membered 5-methylindolin-2-one ring system and the benzene ring is 10.21 (7)°. The atoms C8 in the 5-methylindolin-2-one ring and C10 in the benzene ring are connected by a chain of four atoms (N2/N3/C9/N4)) giving a torsion angle of 7.3 (2)°, while the torsion angles (C8/N2/N3/C9) and (C10/N4/C9/N3) are 173.20 (15)° and -177.56 (16)°, respectively. These values are very close to those in the previously mentioned analogous structure (Qasem Ali et al., 2011). The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H···O1 and C11—H···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1) together with an S(5) N4—H···N2 interaction.
In the crystal the molecules form centrosymmetric cyclic dimers through intermolecular N1—H···O1i hydrogen bonds [graph set R22(8)] (Table 1) (Fig. 2). Weak C—H···π interactions are also present: C5—H5A···Cg3ii = 3.6506 (19) Å; C12—H12A···Cg2iii = 3.6600 (19) Å. [Cg3ii is the centroid of the C10—C15 ring; Cg2iii is the centroid of the C1—C6 ring: symmetry code: (ii) = -x + 1, y + 1/2, -z + 1/2; (iii) = -x, y - 1/2, -z + 1/2].
For related structures, see: Qasem Ali et al. (2011); Ferrari et al. (2002); Pervez et al. (2010); Ramzan et al. (2010). For the biological activity of
see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For the cytotoxic and anticancer activiy of isatin and its derivatives, see: Vine et al. (2009). For bond-length data, see; Allen et al. (1987). For graph-set analysis, see Bernstein et al. (1995).Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C16H14N4OS | F(000) = 648 |
Mr = 310.37 | Dx = 1.387 Mg m−3 |
Monoclinic, P21/c | Melting point = 511.8–512.3 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6875 (3) Å | Cell parameters from 4470 reflections |
b = 17.9405 (8) Å | θ = 3.0–30.2° |
c = 14.5658 (6) Å | µ = 0.23 mm−1 |
β = 91.105 (3)° | T = 100 K |
V = 1485.97 (12) Å3 | Block, orange |
Z = 4 | 0.37 × 0.14 × 0.09 mm |
Bruker APEXII CCD diffractometer | 4645 independent reflections |
Radiation source: fine-focus sealed tube | 3565 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
φ and ω scans | θmax = 30.9°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −8→8 |
Tmin = 0.921, Tmax = 0.980 | k = −25→22 |
25266 measured reflections | l = −20→20 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.044P)2 + 0.9076P] where P = (Fo2 + 2Fc2)/3 |
4645 reflections | (Δ/σ)max < 0.001 |
212 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C16H14N4OS | V = 1485.97 (12) Å3 |
Mr = 310.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.6875 (3) Å | µ = 0.23 mm−1 |
b = 17.9405 (8) Å | T = 100 K |
c = 14.5658 (6) Å | 0.37 × 0.14 × 0.09 mm |
β = 91.105 (3)° |
Bruker APEXII CCD diffractometer | 4645 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3565 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.980 | Rint = 0.080 |
25266 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.40 e Å−3 |
4645 reflections | Δρmin = −0.30 e Å−3 |
212 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 | ||
S1 | 0.07706 (8) | 0.29276 (3) | 0.01263 (3) | 0.02056 (12) | |
O1 | 0.7096 (2) | 0.44974 (7) | 0.01110 (8) | 0.0187 (3) | |
N1 | 0.9164 (3) | 0.52631 (8) | 0.11276 (10) | 0.0179 (3) | |
N2 | 0.3961 (2) | 0.43175 (8) | 0.17539 (10) | 0.0150 (3) | |
N3 | 0.3233 (2) | 0.39394 (8) | 0.09997 (10) | 0.0162 (3) | |
N4 | 0.0280 (2) | 0.34699 (8) | 0.18614 (10) | 0.0159 (3) | |
C1 | 0.6987 (3) | 0.51350 (9) | 0.24304 (12) | 0.0165 (3) | |
C2 | 0.6453 (3) | 0.52430 (10) | 0.33500 (12) | 0.0184 (3) | |
H2A | 0.5077 | 0.5027 | 0.3598 | 0.022* | |
C3 | 0.7961 (3) | 0.56718 (10) | 0.39045 (12) | 0.0193 (3) | |
C4 | 0.9965 (3) | 0.59863 (10) | 0.35161 (13) | 0.0206 (4) | |
H4A | 1.0989 | 0.6276 | 0.3895 | 0.025* | |
C5 | 1.0518 (3) | 0.58900 (10) | 0.25912 (13) | 0.0208 (4) | |
H5A | 1.1879 | 0.6110 | 0.2338 | 0.025* | |
C6 | 0.8998 (3) | 0.54610 (10) | 0.20639 (12) | 0.0169 (3) | |
C7 | 0.7392 (3) | 0.47997 (9) | 0.08672 (12) | 0.0161 (3) | |
C8 | 0.5860 (3) | 0.47119 (9) | 0.16929 (11) | 0.0155 (3) | |
C9 | 0.1363 (3) | 0.34475 (9) | 0.10484 (11) | 0.0149 (3) | |
C10 | −0.1620 (3) | 0.30520 (9) | 0.22098 (11) | 0.0153 (3) | |
C11 | −0.3260 (3) | 0.26716 (9) | 0.16670 (12) | 0.0173 (3) | |
H11A | −0.3118 | 0.2663 | 0.1018 | 0.021* | |
C12 | −0.5113 (3) | 0.23029 (10) | 0.20818 (13) | 0.0200 (3) | |
H12A | −0.6224 | 0.2039 | 0.1711 | 0.024* | |
C13 | −0.5366 (3) | 0.23132 (10) | 0.30262 (13) | 0.0230 (4) | |
H13A | −0.6641 | 0.2060 | 0.3301 | 0.028* | |
C14 | −0.3733 (3) | 0.26977 (12) | 0.35662 (13) | 0.0250 (4) | |
H14A | −0.3896 | 0.2711 | 0.4214 | 0.030* | |
C15 | −0.1861 (3) | 0.30627 (11) | 0.31617 (12) | 0.0218 (4) | |
H15A | −0.0740 | 0.3321 | 0.3535 | 0.026* | |
C16 | 0.7427 (4) | 0.58122 (12) | 0.48997 (13) | 0.0275 (4) | |
H16A | 0.5743 | 0.5738 | 0.4998 | 0.041* | |
H16B | 0.7858 | 0.6325 | 0.5061 | 0.041* | |
H16C | 0.8332 | 0.5465 | 0.5287 | 0.041* | |
H1N4 | 0.095 (4) | 0.3741 (12) | 0.2252 (15) | 0.021 (5)* | |
H1N1 | 1.034 (4) | 0.5376 (13) | 0.0759 (16) | 0.033 (6)* | |
H1N3 | 0.410 (4) | 0.3965 (12) | 0.0486 (15) | 0.026 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0242 (2) | 0.0211 (2) | 0.0166 (2) | −0.00282 (16) | 0.00367 (15) | −0.00340 (17) |
O1 | 0.0170 (6) | 0.0209 (6) | 0.0183 (6) | 0.0005 (5) | 0.0041 (4) | 0.0018 (5) |
N1 | 0.0150 (6) | 0.0184 (7) | 0.0205 (7) | −0.0013 (5) | 0.0072 (5) | 0.0019 (6) |
N2 | 0.0152 (6) | 0.0132 (7) | 0.0166 (7) | 0.0008 (5) | 0.0025 (5) | 0.0017 (5) |
N3 | 0.0167 (6) | 0.0164 (7) | 0.0156 (7) | −0.0017 (5) | 0.0048 (5) | −0.0001 (5) |
N4 | 0.0166 (6) | 0.0164 (7) | 0.0146 (7) | −0.0041 (5) | 0.0029 (5) | −0.0003 (6) |
C1 | 0.0147 (7) | 0.0148 (8) | 0.0199 (8) | −0.0004 (6) | 0.0020 (6) | 0.0027 (6) |
C2 | 0.0191 (8) | 0.0172 (8) | 0.0191 (8) | −0.0015 (6) | 0.0044 (6) | 0.0026 (7) |
C3 | 0.0223 (8) | 0.0152 (8) | 0.0206 (8) | −0.0003 (6) | 0.0015 (6) | 0.0008 (7) |
C4 | 0.0206 (8) | 0.0162 (8) | 0.0250 (9) | −0.0029 (6) | −0.0011 (7) | 0.0012 (7) |
C5 | 0.0161 (7) | 0.0178 (9) | 0.0287 (9) | −0.0025 (6) | 0.0042 (6) | 0.0014 (7) |
C6 | 0.0148 (7) | 0.0148 (8) | 0.0212 (8) | 0.0015 (6) | 0.0040 (6) | 0.0026 (6) |
C7 | 0.0148 (7) | 0.0135 (8) | 0.0204 (8) | 0.0028 (5) | 0.0041 (6) | 0.0055 (6) |
C8 | 0.0136 (7) | 0.0156 (8) | 0.0174 (8) | 0.0007 (6) | 0.0038 (6) | 0.0038 (6) |
C9 | 0.0154 (7) | 0.0137 (8) | 0.0157 (8) | 0.0001 (6) | 0.0014 (6) | 0.0025 (6) |
C10 | 0.0137 (7) | 0.0137 (8) | 0.0186 (8) | −0.0008 (5) | 0.0031 (6) | 0.0028 (6) |
C11 | 0.0172 (7) | 0.0160 (8) | 0.0187 (8) | 0.0011 (6) | 0.0007 (6) | 0.0001 (6) |
C12 | 0.0158 (7) | 0.0162 (8) | 0.0279 (9) | −0.0010 (6) | 0.0002 (6) | −0.0001 (7) |
C13 | 0.0166 (8) | 0.0206 (9) | 0.0319 (10) | −0.0006 (6) | 0.0053 (7) | 0.0069 (7) |
C14 | 0.0205 (8) | 0.0364 (11) | 0.0184 (8) | −0.0023 (7) | 0.0046 (7) | 0.0057 (8) |
C15 | 0.0182 (8) | 0.0296 (10) | 0.0175 (8) | −0.0038 (7) | 0.0011 (6) | 0.0013 (7) |
C16 | 0.0351 (10) | 0.0269 (10) | 0.0205 (9) | −0.0088 (8) | 0.0030 (7) | −0.0025 (8) |
S1—C9 | 1.6643 (17) | C4—C5 | 1.400 (3) |
O1—C7 | 1.236 (2) | C4—H4A | 0.9500 |
N1—C7 | 1.355 (2) | C5—C6 | 1.380 (2) |
N1—C6 | 1.414 (2) | C5—H5A | 0.9500 |
N1—H1N1 | 0.89 (3) | C7—C8 | 1.507 (2) |
N2—C8 | 1.296 (2) | C10—C11 | 1.390 (2) |
N2—N3 | 1.349 (2) | C10—C15 | 1.396 (2) |
N3—C9 | 1.385 (2) | C11—C12 | 1.392 (2) |
N3—H1N3 | 0.91 (2) | C11—H11A | 0.9500 |
N4—C9 | 1.346 (2) | C12—C13 | 1.386 (3) |
N4—C10 | 1.417 (2) | C12—H12A | 0.9500 |
N4—H1N4 | 0.84 (2) | C13—C14 | 1.389 (3) |
C1—C2 | 1.393 (2) | C13—H13A | 0.9500 |
C1—C6 | 1.400 (2) | C14—C15 | 1.391 (2) |
C1—C8 | 1.454 (2) | C14—H14A | 0.9500 |
C2—C3 | 1.397 (2) | C15—H15A | 0.9500 |
C2—H2A | 0.9500 | C16—H16A | 0.9800 |
C3—C4 | 1.401 (2) | C16—H16B | 0.9800 |
C3—C16 | 1.508 (3) | C16—H16C | 0.9800 |
C7—N1—C6 | 111.17 (14) | N2—C8—C1 | 126.19 (15) |
C7—N1—H1N1 | 122.3 (15) | N2—C8—C7 | 127.40 (16) |
C6—N1—H1N1 | 126.2 (15) | C1—C8—C7 | 106.37 (13) |
C8—N2—N3 | 117.49 (14) | N4—C9—N3 | 113.02 (15) |
N2—N3—C9 | 120.16 (14) | N4—C9—S1 | 129.63 (13) |
N2—N3—H1N3 | 119.0 (14) | N3—C9—S1 | 117.35 (12) |
C9—N3—H1N3 | 120.3 (14) | C11—C10—C15 | 119.59 (15) |
C9—N4—C10 | 131.63 (15) | C11—C10—N4 | 124.33 (15) |
C9—N4—H1N4 | 113.8 (15) | C15—C10—N4 | 116.02 (15) |
C10—N4—H1N4 | 114.0 (15) | C10—C11—C12 | 119.45 (16) |
C2—C1—C6 | 120.24 (16) | C10—C11—H11A | 120.3 |
C2—C1—C8 | 133.01 (15) | C12—C11—H11A | 120.3 |
C6—C1—C8 | 106.74 (15) | C13—C12—C11 | 121.24 (17) |
C1—C2—C3 | 119.32 (16) | C13—C12—H12A | 119.4 |
C1—C2—H2A | 120.3 | C11—C12—H12A | 119.4 |
C3—C2—H2A | 120.3 | C12—C13—C14 | 119.17 (17) |
C2—C3—C4 | 118.91 (17) | C12—C13—H13A | 120.4 |
C2—C3—C16 | 120.98 (16) | C14—C13—H13A | 120.4 |
C4—C3—C16 | 120.09 (16) | C13—C14—C15 | 120.20 (17) |
C5—C4—C3 | 122.58 (17) | C13—C14—H14A | 119.9 |
C5—C4—H4A | 118.7 | C15—C14—H14A | 119.9 |
C3—C4—H4A | 118.7 | C14—C15—C10 | 120.33 (17) |
C6—C5—C4 | 117.04 (16) | C14—C15—H15A | 119.8 |
C6—C5—H5A | 121.5 | C10—C15—H15A | 119.8 |
C4—C5—H5A | 121.5 | C3—C16—H16A | 109.5 |
C5—C6—C1 | 121.91 (16) | C3—C16—H16B | 109.5 |
C5—C6—N1 | 128.63 (15) | H16A—C16—H16B | 109.5 |
C1—C6—N1 | 109.45 (15) | C3—C16—H16C | 109.5 |
O1—C7—N1 | 127.33 (15) | H16A—C16—H16C | 109.5 |
O1—C7—C8 | 126.46 (15) | H16B—C16—H16C | 109.5 |
N1—C7—C8 | 106.20 (15) | ||
C8—N2—N3—C9 | 173.20 (15) | C6—C1—C8—N2 | 178.90 (16) |
C6—C1—C2—C3 | −0.8 (3) | C2—C1—C8—C7 | −177.55 (18) |
C8—C1—C2—C3 | 177.80 (17) | C6—C1—C8—C7 | 1.20 (18) |
C1—C2—C3—C4 | 0.5 (3) | O1—C7—C8—N2 | −1.1 (3) |
C1—C2—C3—C16 | 179.03 (17) | N1—C7—C8—N2 | 179.90 (16) |
C2—C3—C4—C5 | 0.2 (3) | O1—C7—C8—C1 | 176.55 (16) |
C16—C3—C4—C5 | −178.40 (18) | N1—C7—C8—C1 | −2.43 (18) |
C3—C4—C5—C6 | −0.5 (3) | C10—N4—C9—N3 | −177.56 (16) |
C4—C5—C6—C1 | 0.1 (3) | C10—N4—C9—S1 | 2.6 (3) |
C4—C5—C6—N1 | −178.48 (17) | N2—N3—C9—N4 | 7.3 (2) |
C2—C1—C6—C5 | 0.5 (3) | N2—N3—C9—S1 | −172.89 (12) |
C8—C1—C6—C5 | −178.41 (16) | C9—N4—C10—C11 | −21.0 (3) |
C2—C1—C6—N1 | 179.35 (15) | C9—N4—C10—C15 | 161.84 (18) |
C8—C1—C6—N1 | 0.42 (19) | C15—C10—C11—C12 | −0.4 (3) |
C7—N1—C6—C5 | 176.62 (17) | N4—C10—C11—C12 | −177.43 (16) |
C7—N1—C6—C1 | −2.1 (2) | C10—C11—C12—C13 | 0.6 (3) |
C6—N1—C7—O1 | −176.20 (16) | C11—C12—C13—C14 | −0.2 (3) |
C6—N1—C7—C8 | 2.77 (18) | C12—C13—C14—C15 | −0.4 (3) |
N3—N2—C8—C1 | −177.47 (15) | C13—C14—C15—C10 | 0.6 (3) |
N3—N2—C8—C7 | −0.2 (2) | C11—C10—C15—C14 | −0.2 (3) |
C2—C1—C8—N2 | 0.2 (3) | N4—C10—C15—C14 | 177.06 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H1N4···N2 | 0.84 (2) | 2.14 (2) | 2.5947 (18) | 114.1 (18) |
N1—H1N1···O1i | 0.89 (2) | 1.96 (2) | 2.848 (2) | 173 (2) |
N3—H1N3···O1 | 0.91 (2) | 2.04 (2) | 2.7595 (17) | 135.8 (19) |
C11—H11A···S1 | 0.95 | 2.63 | 3.2712 (18) | 125 |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H14N4OS |
Mr | 310.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 5.6875 (3), 17.9405 (8), 14.5658 (6) |
β (°) | 91.105 (3) |
V (Å3) | 1485.97 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.37 × 0.14 × 0.09 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.921, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25266, 4645, 3565 |
Rint | 0.080 |
(sin θ/λ)max (Å−1) | 0.722 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.123, 1.06 |
No. of reflections | 4645 |
No. of parameters | 212 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.30 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O1i | 0.89 (2) | 1.96 (2) | 2.848 (2) | 173 (2) |
N3—H1N3···O1 | 0.91 (2) | 2.04 (2) | 2.7595 (17) | 135.8 (19) |
C11—H11A···S1 | 0.95 | 2.63 | 3.2712 (18) | 125 |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing research leave. AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.
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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.
Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. Biological properties of isatin and its derivatives include a range of actions in the brain and offer protection against certain types of infections, such as antibacterial (Suryavanshi & Pai, 2006) antifungal, anticonvulsant, anti-HIV (Pandeya et al., 1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-2-(5-chloro-2- oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (Qasem Ali et al., 2011). In the present paper we describe the single-crystal X-ray diffraction study of title compound, C16H14N4OS.
In this compound (Fig. 1), the dihedral angle between the nine-membered 5-methylindolin-2-one ring system and the benzene ring is 10.21 (7)°. The atoms C8 in the 5-methylindolin-2-one ring and C10 in the benzene ring are connected by a chain of four atoms (N2/N3/C9/N4)) giving a torsion angle of 7.3 (2)°, while the torsion angles (C8/N2/N3/C9) and (C10/N4/C9/N3) are 173.20 (15)° and -177.56 (16)°, respectively. These values are very close to those in the previously mentioned analogous structure (Qasem Ali et al., 2011). The essentially planar conformation of the molecule is maintained by cyclic intramolecular N3—H···O1 and C11—H···S1 hydrogen-bonding interactions [graph set S(6) (Bernstein et al., 1995)] (Table 1) together with an S(5) N4—H···N2 interaction.
In the crystal the molecules form centrosymmetric cyclic dimers through intermolecular N1—H···O1i hydrogen bonds [graph set R22(8)] (Table 1) (Fig. 2). Weak C—H···π interactions are also present: C5—H5A···Cg3ii = 3.6506 (19) Å; C12—H12A···Cg2iii = 3.6600 (19) Å. [Cg3ii is the centroid of the C10—C15 ring; Cg2iii is the centroid of the C1—C6 ring: symmetry code: (ii) = -x + 1, y + 1/2, -z + 1/2; (iii) = -x, y - 1/2, -z + 1/2].