organic compounds
4-Methyl-N′-(2-oxoindolin-3-ylidene)benzene-1-sulfonohydrazide
aEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96201-900, Rio Grande-RS, Brazil, bDepartamento de Química, Universidade Federal de Santa Maria, Av. Roraima, Campus, 97105-900, Santa Maria-RS, Brazil, and cDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000, São Cristóvão-SE, Brazil
*Correspondence e-mail: adriano@daad-alumni.de
In the title compound, C15H13N3O3S, the C—S—N(H)—N linkage is non-planar, the torsion angle being −65.12 (13)° and the S atom showing a tetrahedral environment. The compound has two almost planar fragments linked to the S atom: the isatin-derivative fragment [(C8H5NO)N—N(H)–] and the tolyl fragment [C7H7–] have maximum deviations from the mean plane through the non-H atoms of 0.0813 (13) and 0.0094 (16) Å, respectively, and make an interplanar angle of 80.48 (3)°. In the crystal, molecules are connected into inversion dimers via pairs of N—H⋯O hydrogen bonds. Additionally, the molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond.
Related literature
For the synthesis of isatin-3-tosylhydrazone, see: Cava et al. (1958). For the antifungal and antibacterial properties of isatin derivatives, including the title compound, see: Chohan et al. (2004).
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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536811046605/nc2252sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046605/nc2252Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046605/nc2252Isup3.cml
Starting materials were commercially available and were used without further purification. The synthesis was adapted from a procedure reported previously (Cava et al., 1958). The glacial acetic acid catalyzed reaction of isatin (5 mmol) and p-toluenesulfonylhydrazine (5 mmol) in methanol (60 ml) was refluxed for 5 h. After cooling and filtering, crystals suitable for X-ray diffraction were obtained.
H atoms attached to C atoms were positioned with idealized geometry and were refined isotropic with Ueq(H) set to 1.2 times of the Ueq(C) for the aromatic and 1.5 times of the Ueq(C) for methyl H atoms using a riding model with C—H = 0.93 Å and C—H = 0.96 Å, respectively. H atoms attached to N atoms were located in difference Fourier maps and included in the subsequent
using restraints (N1—H1 = 0.86 (2) Å and N3—H6 = 0.83 (2) Å) with Uiso(H) = 1.2 times of the Ueq(N). In the last stage of they were treated as riding on their parent N atoms.Isatin derivatives have a wide range of biological properties. For example, isatin-based
show pharmacological activity against bacteria and fungi (Chohan et al., 2004). As part of our study of isatin derivatives, we report herein the of isatin-3-tosylhydrazone. In the title compound (Fig. 1) the C—S—N(H)—N linkage is non-planar with the torsion angle being 65.12 (13)° and a tetrahedral environment suggests a sp3 for the S atom. The title structure contains additionally two planar fragments. The mean deviations from the least squares planes for the isatin-derivative fragment C1/C2/C3/C4/C5/C6/C7/C8/N1/N2/N3/O1 and for the tolyl fragment C9/C10/C11/C12/C13/C14/C15 amount to 0.0813 (13)° for C2 and 0.0094 (16)° for C11 atoms, respectively, with a dihedral angle of 80.48 (3)°. The crystal packing is stabilized by intermolecular N—H···O (Table 1; N1—H1···O1i) and also by intramolecular N—H···O bonds (Table 1; N3—H6···O1) leading the isatin-3-tosylhydrazone dimers (Fig. 2). Symmetry code: (i)-x, -y + 2, -z.For the synthesis of isatin-3-tosylhydrazone, see: Cava et al. (1958). For the antifungal and antibacterial properties of isatin derivatives, including the title compound, see: Chohan et al. (2004).
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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C15H13N3O3S | F(000) = 656 |
Mr = 315.35 | Dx = 1.455 Mg m−3 |
Monoclinic, P21/c | Melting point: 476 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.9050 (3) Å | Cell parameters from 4508 reflections |
b = 5.7849 (1) Å | θ = 2.9–26.0° |
c = 17.8112 (3) Å | µ = 0.24 mm−1 |
β = 110.427 (1)° | T = 293 K |
V = 1439.18 (5) Å3 | Block, yellow |
Z = 4 | 0.56 × 0.16 × 0.10 mm |
Bruker X8 APEXII CCD area-detector diffractometer | 4204 independent reflections |
Radiation source: fine-focus sealed tube, Bruker X8 APEXII | 3146 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 30.1°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −20→21 |
Tmin = 0.877, Tmax = 0.976 | k = −8→5 |
15630 measured reflections | l = −25→23 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.4436P] where P = (Fo2 + 2Fc2)/3 |
4204 reflections | (Δ/σ)max = 0.001 |
208 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C15H13N3O3S | V = 1439.18 (5) Å3 |
Mr = 315.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.9050 (3) Å | µ = 0.24 mm−1 |
b = 5.7849 (1) Å | T = 293 K |
c = 17.8112 (3) Å | 0.56 × 0.16 × 0.10 mm |
β = 110.427 (1)° |
Bruker X8 APEXII CCD area-detector diffractometer | 4204 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3146 reflections with I > 2σ(I) |
Tmin = 0.877, Tmax = 0.976 | Rint = 0.026 |
15630 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.28 e Å−3 |
4204 reflections | Δρmin = −0.44 e Å−3 |
208 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 | ||
C3 | 0.11277 (11) | 1.0172 (3) | 0.32467 (9) | 0.0394 (4) | |
H3 | 0.1057 | 1.1188 | 0.3627 | 0.047* | |
C11 | 0.53807 (13) | 0.3670 (4) | 0.17689 (12) | 0.0566 (5) | |
H8 | 0.5908 | 0.3119 | 0.2187 | 0.068* | |
C12 | 0.54616 (13) | 0.5683 (4) | 0.13898 (12) | 0.0527 (5) | |
C10 | 0.45279 (12) | 0.2441 (3) | 0.15401 (11) | 0.0490 (4) | |
H7 | 0.4482 | 0.1086 | 0.1805 | 0.059* | |
C13 | 0.46719 (15) | 0.6454 (4) | 0.07640 (14) | 0.0606 (5) | |
H9 | 0.4717 | 0.7815 | 0.0501 | 0.073* | |
C14 | 0.38184 (13) | 0.5253 (3) | 0.05197 (12) | 0.0540 (5) | |
H10 | 0.3296 | 0.5786 | 0.0094 | 0.065* | |
C15 | 0.63816 (15) | 0.7038 (5) | 0.16498 (16) | 0.0760 (7) | |
H11 | 0.6298 | 0.8449 | 0.1901 | 0.114* | |
H12 | 0.6553 | 0.7391 | 0.1191 | 0.114* | |
H13 | 0.6881 | 0.6138 | 0.2023 | 0.114* | |
H6 | 0.1551 (15) | 0.431 (4) | 0.0260 (12) | 0.059 (6)* | |
H1 | 0.0168 (14) | 1.043 (4) | 0.0776 (12) | 0.055 (6)* | |
S1 | 0.26748 (3) | 0.16782 (7) | 0.06008 (2) | 0.03535 (12) | |
N3 | 0.18364 (9) | 0.3472 (2) | 0.06478 (8) | 0.0352 (3) | |
N2 | 0.19062 (8) | 0.4241 (2) | 0.13897 (7) | 0.0320 (3) | |
C8 | 0.08200 (10) | 0.7533 (3) | 0.07301 (8) | 0.0305 (3) | |
O1 | 0.06596 (8) | 0.71841 (19) | 0.00121 (6) | 0.0382 (3) | |
C9 | 0.37519 (11) | 0.3244 (3) | 0.09182 (9) | 0.0347 (3) | |
N1 | 0.05136 (9) | 0.9330 (2) | 0.10573 (7) | 0.0329 (3) | |
C7 | 0.14177 (10) | 0.6049 (2) | 0.14176 (8) | 0.0292 (3) | |
C1 | 0.08633 (10) | 0.9203 (2) | 0.19011 (8) | 0.0295 (3) | |
O3 | 0.23997 (9) | 0.1214 (2) | −0.02344 (7) | 0.0511 (3) | |
C5 | 0.17706 (11) | 0.6607 (3) | 0.29508 (9) | 0.0353 (3) | |
H5 | 0.2115 | 0.5247 | 0.3121 | 0.042* | |
C2 | 0.07358 (11) | 1.0743 (3) | 0.24401 (9) | 0.0351 (3) | |
H2 | 0.0400 | 1.2115 | 0.2272 | 0.042* | |
C6 | 0.13941 (10) | 0.7169 (2) | 0.21428 (8) | 0.0298 (3) | |
C4 | 0.16212 (11) | 0.8120 (3) | 0.34970 (9) | 0.0398 (4) | |
H4 | 0.1855 | 0.7755 | 0.4040 | 0.048* | |
O2 | 0.27543 (8) | −0.0145 (2) | 0.11553 (8) | 0.0481 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C3 | 0.0415 (8) | 0.0398 (9) | 0.0366 (8) | 0.0005 (7) | 0.0132 (7) | −0.0057 (7) |
C11 | 0.0392 (9) | 0.0670 (13) | 0.0552 (11) | −0.0021 (9) | 0.0060 (8) | −0.0073 (10) |
C12 | 0.0403 (9) | 0.0587 (12) | 0.0630 (12) | −0.0114 (8) | 0.0231 (8) | −0.0226 (10) |
C10 | 0.0454 (9) | 0.0506 (10) | 0.0469 (10) | −0.0021 (8) | 0.0109 (8) | 0.0040 (8) |
C13 | 0.0556 (12) | 0.0479 (11) | 0.0792 (15) | −0.0130 (9) | 0.0247 (10) | 0.0044 (10) |
C14 | 0.0423 (9) | 0.0485 (10) | 0.0646 (12) | −0.0034 (8) | 0.0105 (8) | 0.0089 (9) |
C15 | 0.0501 (12) | 0.0853 (17) | 0.0963 (18) | −0.0272 (12) | 0.0300 (12) | −0.0305 (14) |
S1 | 0.0344 (2) | 0.0308 (2) | 0.0424 (2) | −0.00097 (15) | 0.01533 (16) | −0.00615 (15) |
N3 | 0.0354 (7) | 0.0364 (7) | 0.0338 (7) | 0.0062 (5) | 0.0122 (5) | 0.0009 (6) |
N2 | 0.0333 (6) | 0.0304 (6) | 0.0335 (6) | 0.0027 (5) | 0.0133 (5) | 0.0016 (5) |
C8 | 0.0282 (6) | 0.0315 (7) | 0.0314 (7) | 0.0007 (6) | 0.0101 (5) | 0.0068 (6) |
O1 | 0.0424 (6) | 0.0417 (6) | 0.0294 (5) | 0.0047 (5) | 0.0111 (4) | 0.0051 (5) |
C9 | 0.0322 (7) | 0.0333 (8) | 0.0411 (8) | −0.0007 (6) | 0.0158 (6) | −0.0063 (6) |
N1 | 0.0360 (6) | 0.0308 (6) | 0.0313 (6) | 0.0080 (5) | 0.0109 (5) | 0.0087 (5) |
C7 | 0.0283 (6) | 0.0292 (7) | 0.0303 (7) | 0.0008 (5) | 0.0103 (5) | 0.0059 (6) |
C1 | 0.0287 (6) | 0.0283 (7) | 0.0317 (7) | 0.0007 (5) | 0.0107 (5) | 0.0053 (6) |
O3 | 0.0516 (7) | 0.0557 (8) | 0.0466 (7) | −0.0074 (6) | 0.0177 (6) | −0.0220 (6) |
C5 | 0.0342 (7) | 0.0371 (8) | 0.0319 (7) | 0.0068 (6) | 0.0081 (6) | 0.0063 (6) |
C2 | 0.0364 (7) | 0.0288 (7) | 0.0400 (8) | 0.0040 (6) | 0.0134 (6) | 0.0024 (6) |
C6 | 0.0288 (6) | 0.0295 (7) | 0.0315 (7) | 0.0033 (5) | 0.0109 (5) | 0.0036 (6) |
C4 | 0.0397 (8) | 0.0460 (9) | 0.0293 (7) | 0.0023 (7) | 0.0066 (6) | 0.0014 (7) |
O2 | 0.0449 (6) | 0.0336 (6) | 0.0689 (8) | 0.0029 (5) | 0.0239 (6) | 0.0083 (6) |
C3—C4 | 1.385 (2) | S1—N3 | 1.6488 (13) |
C3—C2 | 1.389 (2) | S1—C9 | 1.7560 (15) |
C3—H3 | 0.9300 | N3—N2 | 1.3636 (17) |
C11—C12 | 1.372 (3) | N3—H6 | 0.83 (2) |
C11—C10 | 1.388 (3) | N2—C7 | 1.2853 (18) |
C11—H8 | 0.9300 | C8—O1 | 1.2329 (17) |
C12—C13 | 1.383 (3) | C8—O1 | 1.2329 (17) |
C12—C15 | 1.505 (3) | C8—N1 | 1.3471 (19) |
C10—C9 | 1.373 (2) | C8—C7 | 1.5060 (19) |
C10—H7 | 0.9300 | N1—C1 | 1.4103 (18) |
C13—C14 | 1.380 (3) | N1—H1 | 0.86 (2) |
C13—H9 | 0.9300 | C7—C6 | 1.456 (2) |
C14—C9 | 1.383 (2) | C1—C2 | 1.371 (2) |
C14—H10 | 0.9300 | C1—C6 | 1.3991 (19) |
C15—H11 | 0.9600 | C5—C4 | 1.383 (2) |
C15—H12 | 0.9600 | C5—C6 | 1.3886 (19) |
C15—H13 | 0.9600 | C5—H5 | 0.9300 |
S1—O2 | 1.4212 (12) | C2—H2 | 0.9300 |
S1—O3 | 1.4239 (12) | C4—H4 | 0.9300 |
C4—C3—C2 | 121.40 (15) | S1—N3—H6 | 120.1 (14) |
C4—C3—H3 | 119.3 | C7—N2—N3 | 116.77 (12) |
C2—C3—H3 | 119.3 | O1—C8—N1 | 127.08 (13) |
C12—C11—C10 | 121.27 (18) | O1—C8—N1 | 127.08 (13) |
C12—C11—H8 | 119.4 | O1—C8—C7 | 126.55 (14) |
C10—C11—H8 | 119.4 | O1—C8—C7 | 126.55 (14) |
C11—C12—C13 | 118.32 (17) | N1—C8—C7 | 106.37 (12) |
C11—C12—C15 | 121.2 (2) | C10—C9—C14 | 120.46 (16) |
C13—C12—C15 | 120.5 (2) | C10—C9—S1 | 120.21 (13) |
C9—C10—C11 | 119.39 (18) | C14—C9—S1 | 119.30 (13) |
C9—C10—H7 | 120.3 | C8—N1—C1 | 111.45 (12) |
C11—C10—H7 | 120.3 | C8—N1—H1 | 122.9 (13) |
C14—C13—C12 | 121.56 (19) | C1—N1—H1 | 125.6 (13) |
C14—C13—H9 | 119.2 | N2—C7—C6 | 125.84 (13) |
C12—C13—H9 | 119.2 | N2—C7—C8 | 127.94 (13) |
C13—C14—C9 | 118.99 (18) | C6—C7—C8 | 106.08 (12) |
C13—C14—H10 | 120.5 | C2—C1—C6 | 122.19 (13) |
C9—C14—H10 | 120.5 | C2—C1—N1 | 128.49 (13) |
C12—C15—H11 | 109.5 | C6—C1—N1 | 109.32 (12) |
C12—C15—H12 | 109.5 | C4—C5—C6 | 118.32 (14) |
H11—C15—H12 | 109.5 | C4—C5—H5 | 120.8 |
C12—C15—H13 | 109.5 | C6—C5—H5 | 120.8 |
H11—C15—H13 | 109.5 | C1—C2—C3 | 117.32 (14) |
H12—C15—H13 | 109.5 | C1—C2—H2 | 121.3 |
O2—S1—O3 | 120.64 (8) | C3—C2—H2 | 121.3 |
O2—S1—N3 | 108.22 (7) | C5—C6—C1 | 119.77 (13) |
O3—S1—N3 | 102.99 (7) | C5—C6—C7 | 133.54 (13) |
O2—S1—C9 | 108.30 (7) | C1—C6—C7 | 106.69 (12) |
O3—S1—C9 | 109.34 (8) | C5—C4—C3 | 120.90 (14) |
N3—S1—C9 | 106.44 (7) | C5—C4—H4 | 119.5 |
N2—N3—S1 | 116.86 (10) | C3—C4—H4 | 119.5 |
N2—N3—H6 | 117.5 (14) | ||
C10—C11—C12—C13 | −0.7 (3) | N3—N2—C7—C6 | −179.42 (13) |
C10—C11—C12—C15 | 178.77 (19) | N3—N2—C7—C8 | −4.3 (2) |
C12—C11—C10—C9 | 0.5 (3) | O1—C8—C7—N2 | 4.0 (2) |
C11—C12—C13—C14 | 0.1 (3) | O1—C8—C7—N2 | 4.0 (2) |
C15—C12—C13—C14 | −179.4 (2) | N1—C8—C7—N2 | −174.84 (14) |
C12—C13—C14—C9 | 0.7 (3) | O1—C8—C7—C6 | 179.91 (14) |
O2—S1—N3—N2 | 51.10 (13) | O1—C8—C7—C6 | 179.91 (14) |
O3—S1—N3—N2 | 179.90 (11) | N1—C8—C7—C6 | 1.06 (15) |
C9—S1—N3—N2 | −65.12 (13) | C8—N1—C1—C2 | 177.47 (14) |
S1—N3—N2—C7 | 162.65 (11) | C8—N1—C1—C6 | −2.60 (16) |
N1—C8—O1—O1 | 0.00 (10) | C6—C1—C2—C3 | −2.3 (2) |
C7—C8—O1—O1 | 0.00 (14) | N1—C1—C2—C3 | 177.61 (14) |
C11—C10—C9—C14 | 0.3 (3) | C4—C3—C2—C1 | −0.5 (2) |
C11—C10—C9—S1 | 178.32 (14) | C4—C5—C6—C1 | −1.2 (2) |
C13—C14—C9—C10 | −0.9 (3) | C4—C5—C6—C7 | 178.95 (15) |
C13—C14—C9—S1 | −178.95 (16) | C2—C1—C6—C5 | 3.2 (2) |
O2—S1—C9—C10 | 8.34 (16) | N1—C1—C6—C5 | −176.70 (13) |
O3—S1—C9—C10 | −124.90 (15) | C2—C1—C6—C7 | −176.92 (13) |
N3—S1—C9—C10 | 124.50 (14) | N1—C1—C6—C7 | 3.15 (15) |
O2—S1—C9—C14 | −173.62 (14) | N2—C7—C6—C5 | −6.7 (3) |
O3—S1—C9—C14 | 53.14 (16) | C8—C7—C6—C5 | 177.26 (16) |
N3—S1—C9—C14 | −57.46 (15) | N2—C7—C6—C1 | 173.44 (14) |
O1—C8—N1—C1 | −177.97 (14) | C8—C7—C6—C1 | −2.56 (15) |
O1—C8—N1—C1 | −177.97 (14) | C6—C5—C4—C3 | −1.5 (2) |
C7—C8—N1—C1 | 0.88 (16) | C2—C3—C4—C5 | 2.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1 | 0.83 (2) | 2.08 (2) | 2.7539 (17) | 138.3 (19) |
N1—H1···O1i | 0.86 (2) | 2.04 (2) | 2.9029 (16) | 172.9 (18) |
Symmetry code: (i) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H13N3O3S |
Mr | 315.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.9050 (3), 5.7849 (1), 17.8112 (3) |
β (°) | 110.427 (1) |
V (Å3) | 1439.18 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.56 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker X8 APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.877, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15630, 4204, 3146 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.113, 1.05 |
No. of reflections | 4204 |
No. of parameters | 208 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.44 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H6···O1 | 0.83 (2) | 2.08 (2) | 2.7539 (17) | 138.3 (19) |
N1—H1···O1i | 0.86 (2) | 2.04 (2) | 2.9029 (16) | 172.9 (18) |
Symmetry code: (i) −x, −y+2, −z. |
Acknowledgements
We gratefully acknowledge Professor Dr Manfredo Hörner (Department of Chemistry, Federal University of Santa Maria, Brazil) for his help and support with the X-ray measurements, and CNPq/FAPERGS for financial support.
References
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cava, M. P., Litle, R. L. & Napier, D. R. (1958). J. Am. Chem. Soc. 80, 2257–2263. CrossRef CAS Web of Science Google Scholar
Chohan, Z. H., Pervez, H., Rauf, A., Khan, K. M. & Supuran, C. T. (2004). J. Enzym. Inhib. Med. Chem. 19, 417–423. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Isatin derivatives have a wide range of biological properties. For example, isatin-based hydrazones show pharmacological activity against bacteria and fungi (Chohan et al., 2004). As part of our study of isatin derivatives, we report herein the crystal structure of isatin-3-tosylhydrazone. In the title compound (Fig. 1) the C—S—N(H)—N linkage is non-planar with the torsion angle being 65.12 (13)° and a tetrahedral environment suggests a sp3 hybridization for the S atom. The title structure contains additionally two planar fragments. The mean deviations from the least squares planes for the isatin-derivative fragment C1/C2/C3/C4/C5/C6/C7/C8/N1/N2/N3/O1 and for the tolyl fragment C9/C10/C11/C12/C13/C14/C15 amount to 0.0813 (13)° for C2 and 0.0094 (16)° for C11 atoms, respectively, with a dihedral angle of 80.48 (3)°. The crystal packing is stabilized by intermolecular N—H···O (Table 1; N1—H1···O1i) and also by intramolecular N—H···O bonds (Table 1; N3—H6···O1) leading the isatin-3-tosylhydrazone dimers (Fig. 2). Symmetry code: (i)-x, -y + 2, -z.