organic compounds
N-Phenyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide
aDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão-SE, Brazil, and bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany
*Correspondence e-mail: adriano@daad-alumni.de
The conformation of the title molecule, C17H17N3S, is stabilized by an intramolecular N—H⋯N hydrogen bond involving the azometinic group. The dihedral angle between the two aromatic rings is 36.49 (06)°. The non-aromatic ring of the tetralone substituent adopts a sofa conformation. In the crystal, molecules are linked by pairs of N—H⋯S hydrogen bonds related via centres of symmetry, forming dimers.
CCDC reference: 982930
Related literature
For the synthesis and pharmacological activity of ketonethiosemicarbazones, see: Thanigaimalai et al. (2011). For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902). For the synthesis and of 2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide, see: de Oliveira et al. (2012).
Experimental
Crystal data
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Data collection: X-AREA (Stoe & Cie, 2008); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008); 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
CCDC reference: 982930
10.1107/S1600536814001585/bt6959sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001585/bt6959Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001585/bt6959Isup3.cml
Starting materials were commercially available and were used without further purification. The tetralone-thiosemicarbazone derivative synthesis was adapted from a procedure reported previously (Freund & Schander, 1902). The hydrochloric acid catalyzed reaction of tetralone (8,83 mmol) and 4-phenylthiosemicarbazide (8,83 mmol) in ethanol (50 ml) was refluxed for 6 h. After cooling and filtering, the title compound was obtained. Crystals suitable for X-ray diffraction of the title compound were obtained in tethahydrofuran by the slow evaporation of solvent.
All H atoms were located in difference map but were positioned with idealized geometry and were refined using a riding model with Uiso(H) = 1.2 Ueq(C and N) with C—H = 0.95 Å for aromatic, C—H = 0.99 Å for methylene and N—H = 0.88 Å for N—H H atoms.
Thiosemicarbazone derivatives have a wide range of pharmacological properties. For example, ketonethiosemicarbazones show pharmacological activity against melanogenesis in melanoma B16 cells (Thanigaimalai et al., 2011). As part of our study on synthesis of thiosemicarbazone compounds, we report herein the
of a derivative of 2-(1,2,3,4-Tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide (Oliveira et al., 2012). The title compound (Figure 1), in which the molecular structure matches the is not planar and the dihedral angle between the two aromatic rings is 36.49 (06)°. The maximum deviation from the mean plane of the non-H atoms for the non-aromatic ring of the tetralone substituent amount to 0.5003 (12) Å for C4, which corresponds to a sofa conformation. The molecule shows a conformation for the atoms about the N2–N1 bond. Due to an intramolecuar hydrogen bond involving the N—H···N atoms (Figure 1), a conformation about the N1–C1 bond is observed. The planarity, atoms distances and angles of the thiosemicarbazone fragment are in agreement with literature data (de Oliveira et al., 2012). The molecules are connected via centrosymmetric pairs of N—H···S, forming dimers (Figure 1, Figure 2 and Table 1).For the synthesis and pharmacological activity of ketonethiosemicarbazones, see: Thanigaimalai et al. (2011). For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902). For the synthesis and
of 2-(1,2,3,4-tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide, see: de Oliveira et al. (2012).Data collection: X-AREA (Stoe & Cie, 2008); cell
X-AREA (Stoe & Cie, 2008); data reduction: X-RED32 (Stoe & Cie, 2008); 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).C17H17N3S | F(000) = 624 |
Mr = 295.40 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/n | Melting point: 452 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4415 (3) Å | Cell parameters from 26099 reflections |
b = 18.0256 (7) Å | θ = 2.3–28.1° |
c = 10.0260 (3) Å | µ = 0.22 mm−1 |
β = 107.495 (2)° | T = 200 K |
V = 1455.02 (9) Å3 | Cubic, yellow |
Z = 4 | 0.3 × 0.3 × 0.2 mm |
Stoe IPDS-1 diffractometer | 3045 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube, Stoe IPDS-1 | Rint = 0.069 |
Graphite monochromator | θmax = 28.1°, θmin = 2.3° |
φ scans | h = −11→11 |
23139 measured reflections | k = −23→23 |
3520 independent reflections | l = −13→12 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.419P] where P = (Fo2 + 2Fc2)/3 |
3520 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C17H17N3S | V = 1455.02 (9) Å3 |
Mr = 295.40 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.4415 (3) Å | µ = 0.22 mm−1 |
b = 18.0256 (7) Å | T = 200 K |
c = 10.0260 (3) Å | 0.3 × 0.3 × 0.2 mm |
β = 107.495 (2)° |
Stoe IPDS-1 diffractometer | 3045 reflections with I > 2σ(I) |
23139 measured reflections | Rint = 0.069 |
3520 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.26 e Å−3 |
3520 reflections | Δρmin = −0.24 e Å−3 |
190 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 | 0.37784 (5) | 0.09351 (2) | 0.54195 (3) | 0.03751 (11) | |
C1 | 0.47689 (15) | 0.07366 (7) | 0.70981 (13) | 0.0270 (3) | |
N1 | 0.55649 (13) | 0.00734 (6) | 0.74440 (11) | 0.0284 (2) | |
H1N | 0.5703 | −0.0195 | 0.6754 | 0.034* | |
N2 | 0.65846 (13) | −0.00109 (6) | 0.88038 (11) | 0.0278 (2) | |
C2 | 0.74837 (15) | −0.06010 (7) | 0.91151 (12) | 0.0250 (2) | |
C3 | 0.74732 (17) | −0.12214 (7) | 0.81071 (13) | 0.0291 (3) | |
H3A | 0.8085 | −0.1061 | 0.7455 | 0.035* | |
H3B | 0.6312 | −0.1327 | 0.7549 | 0.035* | |
C4 | 0.82614 (18) | −0.19283 (7) | 0.88489 (14) | 0.0328 (3) | |
H4A | 0.7561 | −0.2134 | 0.9394 | 0.039* | |
H4B | 0.8337 | −0.2303 | 0.8149 | 0.039* | |
C5 | 0.99852 (18) | −0.17606 (8) | 0.98201 (15) | 0.0363 (3) | |
H5A | 1.0483 | −0.2220 | 1.0311 | 0.044* | |
H5B | 1.0702 | −0.1583 | 0.9265 | 0.044* | |
C6 | 0.99093 (16) | −0.11786 (7) | 1.08793 (14) | 0.0286 (3) | |
C7 | 1.10660 (17) | −0.11733 (8) | 1.22097 (15) | 0.0351 (3) | |
H7 | 1.1929 | −0.1532 | 1.2435 | 0.042* | |
C8 | 1.09825 (18) | −0.06577 (8) | 1.32042 (15) | 0.0383 (3) | |
H8 | 1.1796 | −0.0657 | 1.4097 | 0.046* | |
C9 | 0.9709 (2) | −0.01430 (8) | 1.28947 (14) | 0.0382 (3) | |
H9 | 0.9627 | 0.0203 | 1.3585 | 0.046* | |
C10 | 0.85514 (18) | −0.01313 (7) | 1.15781 (14) | 0.0332 (3) | |
H10 | 0.7684 | 0.0226 | 1.1370 | 0.040* | |
C11 | 0.86494 (15) | −0.06406 (7) | 1.05523 (12) | 0.0262 (3) | |
N3 | 0.48970 (14) | 0.11902 (6) | 0.81878 (11) | 0.0290 (2) | |
H2N | 0.5513 | 0.1028 | 0.9008 | 0.035* | |
C12 | 0.41601 (15) | 0.18985 (7) | 0.81780 (12) | 0.0255 (2) | |
C13 | 0.51258 (16) | 0.24662 (8) | 0.89485 (13) | 0.0303 (3) | |
H13 | 0.6266 | 0.2382 | 0.9427 | 0.036* | |
C14 | 0.44270 (18) | 0.31549 (8) | 0.90199 (14) | 0.0341 (3) | |
H14 | 0.5089 | 0.3542 | 0.9551 | 0.041* | |
C15 | 0.27640 (18) | 0.32813 (8) | 0.83178 (14) | 0.0339 (3) | |
H15 | 0.2284 | 0.3754 | 0.8362 | 0.041* | |
C16 | 0.18101 (16) | 0.27136 (8) | 0.75537 (14) | 0.0323 (3) | |
H16 | 0.0671 | 0.2799 | 0.7071 | 0.039* | |
C17 | 0.24953 (16) | 0.20221 (7) | 0.74832 (13) | 0.0286 (3) | |
H17 | 0.1828 | 0.1634 | 0.6961 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0426 (2) | 0.0436 (2) | 0.02103 (15) | 0.01742 (15) | 0.00155 (13) | −0.00099 (13) |
C1 | 0.0239 (6) | 0.0313 (6) | 0.0248 (6) | 0.0019 (5) | 0.0060 (5) | 0.0000 (5) |
N1 | 0.0290 (5) | 0.0306 (6) | 0.0223 (5) | 0.0048 (4) | 0.0029 (4) | −0.0006 (4) |
N2 | 0.0277 (5) | 0.0311 (6) | 0.0223 (5) | 0.0017 (4) | 0.0040 (4) | 0.0024 (4) |
C2 | 0.0243 (6) | 0.0258 (6) | 0.0246 (6) | −0.0015 (5) | 0.0070 (5) | 0.0022 (4) |
C3 | 0.0313 (6) | 0.0284 (6) | 0.0261 (6) | −0.0019 (5) | 0.0066 (5) | −0.0003 (5) |
C4 | 0.0397 (7) | 0.0266 (6) | 0.0331 (7) | 0.0021 (5) | 0.0125 (6) | −0.0002 (5) |
C5 | 0.0343 (7) | 0.0360 (7) | 0.0395 (7) | 0.0090 (6) | 0.0127 (6) | 0.0045 (6) |
C6 | 0.0252 (6) | 0.0289 (6) | 0.0315 (6) | −0.0017 (5) | 0.0082 (5) | 0.0069 (5) |
C7 | 0.0254 (6) | 0.0386 (7) | 0.0377 (7) | −0.0014 (5) | 0.0038 (5) | 0.0131 (6) |
C8 | 0.0364 (7) | 0.0414 (8) | 0.0292 (6) | −0.0121 (6) | −0.0020 (5) | 0.0101 (6) |
C9 | 0.0509 (9) | 0.0318 (7) | 0.0266 (6) | −0.0076 (6) | 0.0037 (6) | 0.0003 (5) |
C10 | 0.0405 (7) | 0.0268 (7) | 0.0288 (6) | 0.0009 (5) | 0.0050 (5) | 0.0019 (5) |
C11 | 0.0263 (6) | 0.0255 (6) | 0.0254 (6) | −0.0027 (5) | 0.0058 (5) | 0.0044 (4) |
N3 | 0.0294 (5) | 0.0337 (6) | 0.0202 (5) | 0.0072 (4) | 0.0019 (4) | 0.0002 (4) |
C12 | 0.0263 (6) | 0.0297 (6) | 0.0205 (5) | 0.0030 (5) | 0.0069 (4) | 0.0008 (4) |
C13 | 0.0248 (6) | 0.0391 (7) | 0.0242 (6) | −0.0001 (5) | 0.0033 (5) | −0.0019 (5) |
C14 | 0.0360 (7) | 0.0323 (7) | 0.0310 (6) | −0.0038 (5) | 0.0057 (5) | −0.0058 (5) |
C15 | 0.0383 (7) | 0.0303 (7) | 0.0318 (7) | 0.0055 (5) | 0.0086 (6) | −0.0012 (5) |
C16 | 0.0263 (6) | 0.0388 (7) | 0.0292 (6) | 0.0054 (5) | 0.0044 (5) | −0.0012 (5) |
C17 | 0.0255 (6) | 0.0323 (7) | 0.0266 (6) | −0.0014 (5) | 0.0058 (5) | −0.0036 (5) |
S1—C1 | 1.6773 (13) | C7—H7 | 0.9500 |
C1—N3 | 1.3427 (16) | C8—C9 | 1.383 (2) |
C1—N1 | 1.3642 (16) | C8—H8 | 0.9500 |
N1—N2 | 1.3846 (14) | C9—C10 | 1.3864 (19) |
N1—H1N | 0.8800 | C9—H9 | 0.9500 |
N2—C2 | 1.2894 (16) | C10—C11 | 1.3995 (18) |
C2—C11 | 1.4823 (16) | C10—H10 | 0.9500 |
C2—C3 | 1.5055 (18) | N3—C12 | 1.4190 (16) |
C3—C4 | 1.5238 (18) | N3—H2N | 0.8800 |
C3—H3A | 0.9900 | C12—C17 | 1.3861 (18) |
C3—H3B | 0.9900 | C12—C13 | 1.3892 (18) |
C4—C5 | 1.518 (2) | C13—C14 | 1.3854 (19) |
C4—H4A | 0.9900 | C13—H13 | 0.9500 |
C4—H4B | 0.9900 | C14—C15 | 1.387 (2) |
C5—C6 | 1.508 (2) | C14—H14 | 0.9500 |
C5—H5A | 0.9900 | C15—C16 | 1.3826 (19) |
C5—H5B | 0.9900 | C15—H15 | 0.9500 |
C6—C7 | 1.3963 (18) | C16—C17 | 1.3849 (19) |
C6—C11 | 1.4033 (18) | C16—H16 | 0.9500 |
C7—C8 | 1.380 (2) | C17—H17 | 0.9500 |
N3—C1—N1 | 114.44 (11) | C7—C8—C9 | 119.65 (13) |
N3—C1—S1 | 125.48 (10) | C7—C8—H8 | 120.2 |
N1—C1—S1 | 120.06 (9) | C9—C8—H8 | 120.2 |
C1—N1—N2 | 117.35 (10) | C8—C9—C10 | 120.11 (14) |
C1—N1—H1N | 116.9 | C8—C9—H9 | 119.9 |
N2—N1—H1N | 121.6 | C10—C9—H9 | 119.9 |
C2—N2—N1 | 118.38 (11) | C9—C10—C11 | 120.61 (13) |
N2—C2—C11 | 116.45 (11) | C9—C10—H10 | 119.7 |
N2—C2—C3 | 124.48 (11) | C11—C10—H10 | 119.7 |
C11—C2—C3 | 119.01 (11) | C10—C11—C6 | 119.32 (12) |
C2—C3—C4 | 112.33 (10) | C10—C11—C2 | 120.94 (11) |
C2—C3—H3A | 109.1 | C6—C11—C2 | 119.70 (11) |
C4—C3—H3A | 109.1 | C1—N3—C12 | 127.91 (11) |
C2—C3—H3B | 109.1 | C1—N3—H2N | 116.0 |
C4—C3—H3B | 109.1 | C12—N3—H2N | 116.0 |
H3A—C3—H3B | 107.9 | C17—C12—C13 | 119.87 (12) |
C5—C4—C3 | 109.89 (11) | C17—C12—N3 | 121.61 (11) |
C5—C4—H4A | 109.7 | C13—C12—N3 | 118.44 (11) |
C3—C4—H4A | 109.7 | C14—C13—C12 | 120.06 (12) |
C5—C4—H4B | 109.7 | C14—C13—H13 | 120.0 |
C3—C4—H4B | 109.7 | C12—C13—H13 | 120.0 |
H4A—C4—H4B | 108.2 | C13—C14—C15 | 120.17 (13) |
C6—C5—C4 | 110.78 (11) | C13—C14—H14 | 119.9 |
C6—C5—H5A | 109.5 | C15—C14—H14 | 119.9 |
C4—C5—H5A | 109.5 | C16—C15—C14 | 119.45 (13) |
C6—C5—H5B | 109.5 | C16—C15—H15 | 120.3 |
C4—C5—H5B | 109.5 | C14—C15—H15 | 120.3 |
H5A—C5—H5B | 108.1 | C15—C16—C17 | 120.79 (12) |
C7—C6—C11 | 118.80 (13) | C15—C16—H16 | 119.6 |
C7—C6—C5 | 120.80 (12) | C17—C16—H16 | 119.6 |
C11—C6—C5 | 120.40 (12) | C16—C17—C12 | 119.66 (12) |
C8—C7—C6 | 121.45 (13) | C16—C17—H17 | 120.2 |
C8—C7—H7 | 119.3 | C12—C17—H17 | 120.2 |
C6—C7—H7 | 119.3 | ||
N3—C1—N1—N2 | −9.03 (16) | C5—C6—C11—C10 | 176.54 (12) |
S1—C1—N1—N2 | 169.57 (9) | C7—C6—C11—C2 | 175.51 (11) |
C1—N1—N2—C2 | −172.78 (11) | C5—C6—C11—C2 | −5.79 (18) |
N1—N2—C2—C11 | 175.47 (10) | N2—C2—C11—C10 | 11.35 (18) |
N1—N2—C2—C3 | −1.69 (18) | C3—C2—C11—C10 | −171.33 (12) |
N2—C2—C3—C4 | −163.68 (12) | N2—C2—C11—C6 | −166.29 (11) |
C11—C2—C3—C4 | 19.23 (16) | C3—C2—C11—C6 | 11.04 (17) |
C2—C3—C4—C5 | −53.39 (15) | N1—C1—N3—C12 | −177.29 (12) |
C3—C4—C5—C6 | 58.18 (15) | S1—C1—N3—C12 | 4.2 (2) |
C4—C5—C6—C7 | 149.58 (12) | C1—N3—C12—C17 | 47.42 (19) |
C4—C5—C6—C11 | −29.09 (17) | C1—N3—C12—C13 | −135.95 (14) |
C11—C6—C7—C8 | 0.67 (19) | C17—C12—C13—C14 | −0.13 (19) |
C5—C6—C7—C8 | −178.02 (13) | N3—C12—C13—C14 | −176.81 (12) |
C6—C7—C8—C9 | 1.4 (2) | C12—C13—C14—C15 | −0.3 (2) |
C7—C8—C9—C10 | −1.9 (2) | C13—C14—C15—C16 | 0.3 (2) |
C8—C9—C10—C11 | 0.4 (2) | C14—C15—C16—C17 | 0.1 (2) |
C9—C10—C11—C6 | 1.6 (2) | C15—C16—C17—C12 | −0.5 (2) |
C9—C10—C11—C2 | −175.99 (12) | C13—C12—C17—C16 | 0.51 (19) |
C7—C6—C11—C10 | −2.16 (18) | N3—C12—C17—C16 | 177.09 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···S1i | 0.88 | 2.70 | 3.5793 (11) | 176 |
N3—H2N···N2 | 0.88 | 2.12 | 2.5630 (15) | 111 |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···S1i | 0.88 | 2.70 | 3.5793 (11) | 176.1 |
N3—H2N···N2 | 0.88 | 2.12 | 2.5630 (15) | 110.6 |
Symmetry code: (i) −x+1, −y, −z+1. |
Acknowledgements
We gratefully acknowledge financial support by the State of Schleswig–Holstein, Germany. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities. BRSF thanks CNPq/UFS for the award of a PIBIC scholarship and ABO acknowledges financial support through the FAPITEC/SE/FUNTEC/CNPq PPP 04/2011 program.
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Thiosemicarbazone derivatives have a wide range of pharmacological properties. For example, ketonethiosemicarbazones show pharmacological activity against melanogenesis in melanoma B16 cells (Thanigaimalai et al., 2011). As part of our study on synthesis of thiosemicarbazone compounds, we report herein the crystal structure of a derivative of 2-(1,2,3,4-Tetrahydronaphthalen-1-ylidene)hydrazinecarbothioamide (Oliveira et al., 2012). The title compound (Figure 1), in which the molecular structure matches the asymmetric unit, is not planar and the dihedral angle between the two aromatic rings is 36.49 (06)°. The maximum deviation from the mean plane of the non-H atoms for the non-aromatic ring of the tetralone substituent amount to 0.5003 (12) Å for C4, which corresponds to a sofa conformation. The molecule shows a trans conformation for the atoms about the N2–N1 bond. Due to an intramolecuar hydrogen bond involving the N—H···N atoms (Figure 1), a cis conformation about the N1–C1 bond is observed. The planarity, atoms distances and angles of the thiosemicarbazone fragment are in agreement with literature data (de Oliveira et al., 2012). The molecules are connected via centrosymmetric pairs of N—H···S, forming dimers (Figure 1, Figure 2 and Table 1).