organic compounds
N-Methyl-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
There are two independent molecules in the 12H15N3S, both of which display disorder of several C atoms in the N-bound ring (occupancy ratios of 0.75:0.25 in the first independent molecule and 0.50:0.50 in the second) with the methyl H atoms also being disordered in the first molecule (occupancy ratio of 0.70:0.30). The planes of the benzene ring and the N—N—C—N fragment make dihedral angles of 12.92 (14)° in the first independent molecule and 7.60 (13)° in the second. In the crystal, molecules are linked by weak N—H⋯S hydrogen bonds into chains along the a-axis direction. The crystal packing ressembles a herringbone arrangement.
of the title compound, CCCDC reference: 986205
Related literature
For the synthesis, coordination chemistry and biological activity of thiosemicarbazones, see: Lobana et al. (2009). For one of the first reports of the synthesis of thiosemicarbazone derivatives, see: Freund & Schander (1902).
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: 986205
10.1107/S1600536814003079/bt6960sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003079/bt6960Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003079/bt6960Isup3.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-methylthiosemicarbazide (8,83 mmol) in ethanol (50 ml) was refluxed for 6 h. After cooling and filtering, the title compound was obtained as a solid. Crystals suitable for X-ray diffraction of the title compound were obtained in tethahydrofuran by the slow evaporation of solvent.
All non-hydrogen atoms were refined anisotropic. All H atoms were located in difference map but were positioned with idealized geometry (methyl H atoms allowed to rotate but no to tip) and were refined isotropic with Uiso(H) = 1,2 Ueq(C) (1,5 for methyl H atoms) using a riding model with C—H = 0,95 Å for aromatic and C—H = 0,99 Å for methylene. The N—H H atoms were located in difference map and refined with varying coordinates and varying isotropic displacement parameters. There are two crystallographically independent molecules in the
In both of them several C atoms disordered (C3, C4 and C23) and were refined using a split model. The methyl C12 H atoms are disordered and were refined in two orientations.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).C12H15N3S | Z = 4 |
Mr = 233.33 | F(000) = 496 |
Triclinic, P1 | Dx = 1.280 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6234 (6) Å | Cell parameters from 11521 reflections |
b = 10.9425 (6) Å | θ = 1.9–27.0° |
c = 11.0576 (6) Å | µ = 0.24 mm−1 |
α = 73.685 (4)° | T = 200 K |
β = 79.152 (4)° | Block, white |
γ = 88.614 (4)° | 0.2 × 0.1 × 0.1 mm |
V = 1211.04 (12) Å3 |
Stoe IPDS-1 diffractometer | 4111 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube, Stoe IPDS-1 | Rint = 0.031 |
Graphite monochromator | θmax = 27.0°, θmin = 1.9° |
φ scans | h = −13→12 |
11521 measured reflections | k = −13→13 |
5125 independent reflections | l = −14→13 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2784P] where P = (Fo2 + 2Fc2)/3 |
5125 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C12H15N3S | γ = 88.614 (4)° |
Mr = 233.33 | V = 1211.04 (12) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.6234 (6) Å | Mo Kα radiation |
b = 10.9425 (6) Å | µ = 0.24 mm−1 |
c = 11.0576 (6) Å | T = 200 K |
α = 73.685 (4)° | 0.2 × 0.1 × 0.1 mm |
β = 79.152 (4)° |
Stoe IPDS-1 diffractometer | 4111 reflections with I > 2σ(I) |
11521 measured reflections | Rint = 0.031 |
5125 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.42 e Å−3 |
5125 reflections | Δρmin = −0.42 e Å−3 |
334 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 | Occ. (<1) | |
C1 | 0.48672 (15) | 0.18650 (14) | 0.58968 (14) | 0.0359 (3) | |
C2 | 0.5663 (2) | 0.2436 (2) | 0.65971 (16) | 0.0585 (5) | |
H2A | 0.5465 | 0.3348 | 0.6461 | 0.070* | 0.75 |
H2B | 0.6581 | 0.2385 | 0.6229 | 0.070* | 0.75 |
H2C | 0.5993 | 0.3292 | 0.6057 | 0.070* | 0.25 |
H2D | 0.6406 | 0.1896 | 0.6772 | 0.070* | 0.25 |
C3 | 0.5434 (3) | 0.1769 (3) | 0.8050 (2) | 0.0523 (6) | 0.75 |
H3A | 0.5785 | 0.0904 | 0.8205 | 0.063* | 0.75 |
H3B | 0.5878 | 0.2259 | 0.8483 | 0.063* | 0.75 |
C4 | 0.4004 (7) | 0.1680 (7) | 0.8593 (8) | 0.0515 (13) | 0.75 |
H4A | 0.3634 | 0.2536 | 0.8400 | 0.062* | 0.75 |
H4B | 0.3844 | 0.1303 | 0.9535 | 0.062* | 0.75 |
C3' | 0.4840 (13) | 0.2542 (11) | 0.7888 (8) | 0.074 (3) | 0.25 |
H3C | 0.5398 | 0.2787 | 0.8411 | 0.088* | 0.25 |
H3D | 0.4196 | 0.3207 | 0.7715 | 0.088* | 0.25 |
C4' | 0.420 (3) | 0.133 (2) | 0.858 (3) | 0.071 (7) | 0.25 |
H4C | 0.4868 | 0.0699 | 0.8806 | 0.085* | 0.25 |
H4D | 0.3683 | 0.1411 | 0.9392 | 0.085* | 0.25 |
C5 | 0.34020 (17) | 0.08243 (17) | 0.79474 (15) | 0.0456 (4) | |
C6 | 0.24021 (19) | −0.00422 (19) | 0.86362 (18) | 0.0570 (5) | |
H6 | 0.2117 | −0.0132 | 0.9525 | 0.068* | |
C7 | 0.18239 (19) | −0.07657 (18) | 0.8054 (2) | 0.0582 (5) | |
H7 | 0.1152 | −0.1359 | 0.8542 | 0.070* | |
C8 | 0.22184 (17) | −0.06331 (16) | 0.67515 (19) | 0.0497 (4) | |
H8 | 0.1809 | −0.1126 | 0.6345 | 0.060* | |
C9 | 0.32074 (15) | 0.02177 (14) | 0.60490 (16) | 0.0396 (3) | |
H9 | 0.3479 | 0.0307 | 0.5159 | 0.048* | |
C10 | 0.38118 (15) | 0.09484 (13) | 0.66391 (14) | 0.0350 (3) | |
N1 | 0.50410 (13) | 0.21270 (11) | 0.46681 (12) | 0.0354 (3) | |
N2 | 0.60085 (15) | 0.29850 (14) | 0.39563 (12) | 0.0430 (3) | |
H2 | 0.652 (2) | 0.3371 (19) | 0.431 (2) | 0.056 (6)* | |
C11 | 0.62069 (17) | 0.32887 (15) | 0.26515 (14) | 0.0420 (4) | |
S1 | 0.73841 (6) | 0.43493 (5) | 0.17704 (4) | 0.06437 (17) | |
N3 | 0.54320 (15) | 0.27078 (15) | 0.21718 (13) | 0.0441 (3) | |
H3 | 0.486 (2) | 0.215 (2) | 0.272 (2) | 0.057 (6)* | |
C12 | 0.5478 (2) | 0.2904 (2) | 0.08134 (17) | 0.0624 (5) | |
H12A | 0.4843 | 0.2334 | 0.0693 | 0.094* | 0.70 |
H12B | 0.6336 | 0.2719 | 0.0410 | 0.094* | 0.70 |
H12C | 0.5285 | 0.3790 | 0.0418 | 0.094* | 0.70 |
H12D | 0.6133 | 0.3561 | 0.0321 | 0.094* | 0.30 |
H12E | 0.4640 | 0.3177 | 0.0604 | 0.094* | 0.30 |
H12F | 0.5691 | 0.2105 | 0.0596 | 0.094* | 0.30 |
C21 | 1.03532 (14) | 0.72157 (13) | 0.43323 (14) | 0.0345 (3) | |
C22 | 0.98459 (18) | 0.80910 (17) | 0.32295 (15) | 0.0463 (4) | |
H22A | 0.9799 | 0.8963 | 0.3330 | 0.056* | 0.50 |
H22B | 0.8968 | 0.7801 | 0.3238 | 0.056* | 0.50 |
H22C | 1.0370 | 0.8893 | 0.2905 | 0.056* | 0.50 |
H22D | 0.8954 | 0.8305 | 0.3536 | 0.056* | 0.50 |
C23 | 1.0710 (4) | 0.8118 (3) | 0.1933 (3) | 0.0439 (7) | 0.50 |
H23A | 1.0273 | 0.8583 | 0.1231 | 0.053* | 0.50 |
H23B | 1.1517 | 0.8596 | 0.1847 | 0.053* | 0.50 |
C23' | 0.9870 (4) | 0.7468 (4) | 0.2094 (3) | 0.0527 (9) | 0.50 |
H23C | 0.9161 | 0.6824 | 0.2339 | 0.063* | 0.50 |
H23D | 0.9720 | 0.8135 | 0.1324 | 0.063* | 0.50 |
C24 | 1.1012 (3) | 0.6896 (3) | 0.1790 (2) | 0.0752 (7) | |
H24A | 1.1638 | 0.6994 | 0.0981 | 0.090* | 0.50 |
H24B | 1.0225 | 0.6481 | 0.1713 | 0.090* | 0.50 |
H24C | 1.1662 | 0.7578 | 0.1307 | 0.090* | 0.50 |
H24D | 1.0891 | 0.6392 | 0.1202 | 0.090* | 0.50 |
C25 | 1.15584 (17) | 0.60384 (17) | 0.28740 (17) | 0.0451 (4) | |
C26 | 1.23846 (19) | 0.50776 (19) | 0.2683 (2) | 0.0562 (5) | |
H26 | 1.2618 | 0.4967 | 0.1848 | 0.067* | |
C27 | 1.28696 (19) | 0.42841 (18) | 0.3681 (2) | 0.0571 (5) | |
H27 | 1.3434 | 0.3633 | 0.3533 | 0.069* | |
C28 | 1.25370 (17) | 0.44333 (17) | 0.4896 (2) | 0.0518 (4) | |
H28 | 1.2872 | 0.3885 | 0.5585 | 0.062* | |
C29 | 1.17199 (15) | 0.53750 (15) | 0.51113 (17) | 0.0424 (4) | |
H29 | 1.1488 | 0.5468 | 0.5953 | 0.051* | |
C30 | 1.12244 (14) | 0.61990 (14) | 0.41059 (14) | 0.0352 (3) | |
N21 | 1.00717 (13) | 0.72885 (12) | 0.54928 (12) | 0.0378 (3) | |
N22 | 0.92325 (15) | 0.81998 (13) | 0.57445 (13) | 0.0417 (3) | |
H22 | 0.883 (2) | 0.8683 (19) | 0.517 (2) | 0.055 (6)* | |
C31 | 0.87550 (17) | 0.81552 (16) | 0.69932 (15) | 0.0420 (4) | |
S21 | 0.76008 (5) | 0.91523 (5) | 0.73333 (5) | 0.05696 (15) | |
N23 | 0.92760 (17) | 0.73086 (15) | 0.78559 (13) | 0.0475 (3) | |
H23 | 0.985 (2) | 0.683 (2) | 0.762 (2) | 0.059 (6)* | |
C32 | 0.8857 (2) | 0.7063 (2) | 0.92353 (17) | 0.0637 (6) | |
H32A | 0.8908 | 0.7858 | 0.9470 | 0.096* | |
H32B | 0.9411 | 0.6437 | 0.9682 | 0.096* | |
H32C | 0.7969 | 0.6730 | 0.9483 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0370 (8) | 0.0407 (7) | 0.0292 (7) | −0.0037 (6) | −0.0035 (6) | −0.0102 (6) |
C2 | 0.0602 (12) | 0.0828 (13) | 0.0308 (8) | −0.0339 (10) | −0.0013 (8) | −0.0151 (8) |
C3 | 0.0488 (15) | 0.0784 (19) | 0.0313 (11) | −0.0160 (13) | −0.0046 (10) | −0.0188 (12) |
C4 | 0.056 (2) | 0.069 (4) | 0.0309 (16) | −0.015 (2) | 0.0027 (16) | −0.022 (2) |
C3' | 0.106 (9) | 0.081 (6) | 0.036 (4) | −0.049 (6) | 0.009 (5) | −0.029 (4) |
C4' | 0.107 (14) | 0.068 (12) | 0.031 (5) | −0.022 (8) | 0.022 (7) | −0.023 (7) |
C5 | 0.0455 (10) | 0.0531 (9) | 0.0329 (8) | −0.0093 (7) | −0.0038 (7) | −0.0048 (7) |
C6 | 0.0531 (11) | 0.0669 (12) | 0.0377 (9) | −0.0157 (9) | −0.0003 (8) | 0.0026 (8) |
C7 | 0.0479 (11) | 0.0510 (10) | 0.0615 (12) | −0.0149 (8) | −0.0065 (9) | 0.0059 (8) |
C8 | 0.0417 (9) | 0.0410 (8) | 0.0666 (11) | −0.0041 (7) | −0.0151 (9) | −0.0117 (8) |
C9 | 0.0355 (8) | 0.0406 (8) | 0.0439 (8) | 0.0026 (6) | −0.0093 (7) | −0.0127 (6) |
C10 | 0.0343 (8) | 0.0354 (7) | 0.0327 (7) | 0.0005 (6) | −0.0065 (6) | −0.0052 (6) |
N1 | 0.0377 (7) | 0.0373 (6) | 0.0296 (6) | −0.0036 (5) | −0.0033 (5) | −0.0084 (5) |
N2 | 0.0479 (8) | 0.0508 (8) | 0.0276 (6) | −0.0152 (6) | −0.0011 (6) | −0.0093 (5) |
C11 | 0.0476 (10) | 0.0462 (8) | 0.0291 (7) | −0.0023 (7) | −0.0021 (7) | −0.0088 (6) |
S1 | 0.0763 (4) | 0.0707 (3) | 0.0348 (2) | −0.0303 (3) | 0.0012 (2) | −0.0016 (2) |
N3 | 0.0461 (8) | 0.0577 (8) | 0.0271 (6) | −0.0038 (7) | −0.0032 (6) | −0.0119 (6) |
C12 | 0.0653 (13) | 0.0932 (15) | 0.0298 (8) | −0.0070 (11) | −0.0084 (8) | −0.0189 (9) |
C21 | 0.0342 (8) | 0.0374 (7) | 0.0304 (7) | −0.0045 (6) | −0.0047 (6) | −0.0078 (6) |
C22 | 0.0542 (11) | 0.0497 (9) | 0.0317 (8) | 0.0123 (8) | −0.0068 (7) | −0.0079 (7) |
C23 | 0.0446 (19) | 0.0546 (19) | 0.0265 (14) | −0.0051 (15) | −0.0023 (13) | −0.0039 (13) |
C23' | 0.059 (2) | 0.069 (2) | 0.0328 (16) | 0.016 (2) | −0.0152 (16) | −0.0156 (16) |
C24 | 0.0950 (18) | 0.0995 (17) | 0.0404 (10) | 0.0374 (14) | −0.0212 (11) | −0.0322 (11) |
C25 | 0.0414 (9) | 0.0532 (9) | 0.0446 (9) | 0.0016 (7) | −0.0067 (7) | −0.0210 (7) |
C26 | 0.0478 (11) | 0.0641 (11) | 0.0641 (12) | 0.0030 (9) | −0.0033 (9) | −0.0347 (10) |
C27 | 0.0423 (10) | 0.0481 (10) | 0.0848 (14) | 0.0060 (8) | −0.0100 (10) | −0.0267 (9) |
C28 | 0.0390 (9) | 0.0434 (9) | 0.0697 (12) | 0.0016 (7) | −0.0139 (9) | −0.0085 (8) |
C29 | 0.0361 (9) | 0.0424 (8) | 0.0460 (9) | −0.0040 (6) | −0.0085 (7) | −0.0073 (7) |
C30 | 0.0284 (7) | 0.0380 (7) | 0.0385 (8) | −0.0057 (6) | −0.0039 (6) | −0.0107 (6) |
N21 | 0.0401 (7) | 0.0409 (7) | 0.0331 (6) | 0.0004 (5) | −0.0065 (5) | −0.0118 (5) |
N22 | 0.0489 (8) | 0.0447 (7) | 0.0316 (6) | 0.0046 (6) | −0.0058 (6) | −0.0123 (5) |
C31 | 0.0448 (9) | 0.0472 (8) | 0.0358 (8) | −0.0119 (7) | −0.0016 (7) | −0.0172 (7) |
S21 | 0.0551 (3) | 0.0707 (3) | 0.0517 (3) | 0.0034 (2) | −0.0019 (2) | −0.0334 (2) |
N23 | 0.0555 (10) | 0.0538 (8) | 0.0313 (7) | −0.0079 (7) | −0.0036 (6) | −0.0114 (6) |
C32 | 0.0733 (14) | 0.0818 (14) | 0.0308 (8) | −0.0207 (11) | −0.0003 (9) | −0.0119 (8) |
C1—N1 | 1.2851 (19) | C12—H12E | 0.9800 |
C1—C10 | 1.477 (2) | C12—H12F | 0.9800 |
C1—C2 | 1.499 (2) | C21—N21 | 1.2863 (19) |
C2—C3 | 1.541 (3) | C21—C30 | 1.475 (2) |
C2—C3' | 1.560 (9) | C21—C22 | 1.504 (2) |
C2—H2A | 0.9900 | C22—C23 | 1.543 (3) |
C2—H2B | 0.9900 | C22—C23' | 1.584 (4) |
C2—H2C | 0.9900 | C22—H22A | 0.9900 |
C2—H2D | 0.9900 | C22—H22B | 0.9900 |
C3—C4 | 1.519 (8) | C22—H22C | 0.9900 |
C3—H3A | 0.9900 | C22—H22D | 0.9900 |
C3—H3B | 0.9900 | C23—C24 | 1.412 (4) |
C4—C5 | 1.540 (6) | C23—H23A | 0.9900 |
C4—H4A | 0.9900 | C23—H23B | 0.9900 |
C4—H4B | 0.9900 | C23'—C24 | 1.380 (4) |
C3'—C4' | 1.45 (3) | C23'—H23C | 0.9900 |
C3'—H3C | 0.9900 | C23'—H23D | 0.9900 |
C3'—H3D | 0.9900 | C24—C25 | 1.502 (3) |
C4'—C5 | 1.41 (3) | C24—H24A | 0.9900 |
C4'—H4C | 0.9900 | C24—H24B | 0.9900 |
C4'—H4D | 0.9900 | C24—H24C | 0.9900 |
C5—C6 | 1.395 (2) | C24—H24D | 0.9900 |
C5—C10 | 1.399 (2) | C25—C26 | 1.390 (3) |
C6—C7 | 1.370 (3) | C25—C30 | 1.401 (2) |
C6—H6 | 0.9500 | C26—C27 | 1.375 (3) |
C7—C8 | 1.389 (3) | C26—H26 | 0.9500 |
C7—H7 | 0.9500 | C27—C28 | 1.377 (3) |
C8—C9 | 1.381 (2) | C27—H27 | 0.9500 |
C8—H8 | 0.9500 | C28—C29 | 1.374 (3) |
C9—C10 | 1.398 (2) | C28—H28 | 0.9500 |
C9—H9 | 0.9500 | C29—C30 | 1.400 (2) |
N1—N2 | 1.3727 (18) | C29—H29 | 0.9500 |
N2—C11 | 1.362 (2) | N21—N22 | 1.373 (2) |
N2—H2 | 0.90 (2) | N22—C31 | 1.366 (2) |
C11—N3 | 1.320 (2) | N22—H22 | 0.88 (2) |
C11—S1 | 1.6841 (17) | C31—N23 | 1.324 (2) |
N3—C12 | 1.448 (2) | C31—S21 | 1.6816 (18) |
N3—H3 | 0.88 (2) | N23—C32 | 1.455 (2) |
C12—H12A | 0.9800 | N23—H23 | 0.85 (2) |
C12—H12B | 0.9800 | C32—H32A | 0.9800 |
C12—H12C | 0.9800 | C32—H32B | 0.9800 |
C12—H12D | 0.9800 | C32—H32C | 0.9800 |
N1—C1—C10 | 116.87 (13) | H12D—C12—H12F | 109.5 |
N1—C1—C2 | 123.86 (14) | H12E—C12—H12F | 109.5 |
C10—C1—C2 | 119.27 (13) | N21—C21—C30 | 116.47 (13) |
C1—C2—C3 | 113.13 (16) | N21—C21—C22 | 123.90 (14) |
C1—C2—C3' | 110.1 (4) | C30—C21—C22 | 119.63 (13) |
C1—C2—H2A | 109.0 | C21—C22—C23 | 111.25 (18) |
C3—C2—H2A | 109.0 | C21—C22—C23' | 111.96 (18) |
C1—C2—H2B | 109.0 | C21—C22—H22A | 109.4 |
C3—C2—H2B | 109.0 | C23—C22—H22A | 109.4 |
H2A—C2—H2B | 107.8 | C23'—C22—H22A | 136.4 |
C1—C2—H2C | 109.6 | C21—C22—H22B | 109.4 |
C3—C2—H2C | 134.0 | C23—C22—H22B | 109.4 |
C3'—C2—H2C | 109.6 | C23'—C22—H22B | 70.4 |
C1—C2—H2D | 109.6 | H22A—C22—H22B | 108.0 |
C3'—C2—H2D | 109.6 | C21—C22—H22C | 109.2 |
H2A—C2—H2D | 136.7 | C23—C22—H22C | 70.8 |
H2C—C2—H2D | 108.2 | C23'—C22—H22C | 109.2 |
C4—C3—C2 | 109.4 (4) | H22B—C22—H22C | 137.9 |
C4—C3—H3A | 109.8 | C21—C22—H22D | 109.2 |
C2—C3—H3A | 109.8 | C23'—C22—H22D | 109.2 |
C4—C3—H3B | 109.8 | H22C—C22—H22D | 107.9 |
C2—C3—H3B | 109.8 | C24—C23—C22 | 113.7 (2) |
H3A—C3—H3B | 108.2 | C24—C23—H23A | 108.8 |
C3—C4—C5 | 106.5 (4) | C22—C23—H23A | 108.8 |
C3—C4—H4A | 110.4 | C24—C23—H23B | 108.8 |
C5—C4—H4A | 110.4 | C22—C23—H23B | 108.8 |
C3—C4—H4B | 110.4 | H23A—C23—H23B | 107.7 |
C5—C4—H4B | 110.4 | C24—C23'—C22 | 113.0 (3) |
H4A—C4—H4B | 108.6 | C24—C23'—H23C | 109.0 |
C4'—C3'—C2 | 109.1 (11) | C22—C23'—H23C | 109.0 |
C4'—C3'—H3C | 109.9 | C24—C23'—H23D | 109.0 |
C2—C3'—H3C | 109.9 | C22—C23'—H23D | 109.0 |
C4'—C3'—H3D | 109.9 | H23C—C23'—H23D | 107.8 |
C2—C3'—H3D | 109.9 | C23'—C24—C25 | 117.8 (2) |
H3C—C3'—H3D | 108.3 | C23—C24—C25 | 114.3 (2) |
C5—C4'—C3' | 116.9 (19) | C23'—C24—H24A | 133.1 |
C5—C4'—H4C | 108.1 | C23—C24—H24A | 108.7 |
C3'—C4'—H4C | 108.1 | C25—C24—H24A | 108.7 |
C5—C4'—H4D | 108.1 | C23—C24—H24B | 108.7 |
C3'—C4'—H4D | 108.1 | C25—C24—H24B | 108.7 |
H4C—C4'—H4D | 107.3 | H24A—C24—H24B | 107.6 |
C6—C5—C10 | 118.82 (16) | C23'—C24—H24C | 107.9 |
C6—C5—C4' | 121.1 (11) | C25—C24—H24C | 107.9 |
C10—C5—C4' | 118.1 (11) | H24B—C24—H24C | 141.8 |
C6—C5—C4 | 120.9 (3) | C23'—C24—H24D | 107.9 |
C10—C5—C4 | 120.2 (3) | C23—C24—H24D | 137.6 |
C4'—C5—C4 | 16.3 (11) | C25—C24—H24D | 107.9 |
C7—C6—C5 | 121.20 (17) | H24C—C24—H24D | 107.2 |
C7—C6—H6 | 119.4 | C26—C25—C30 | 119.05 (17) |
C5—C6—H6 | 119.4 | C26—C25—C24 | 121.30 (17) |
C6—C7—C8 | 120.10 (16) | C30—C25—C24 | 119.65 (16) |
C6—C7—H7 | 119.9 | C27—C26—C25 | 121.11 (19) |
C8—C7—H7 | 119.9 | C27—C26—H26 | 119.4 |
C9—C8—C7 | 119.78 (16) | C25—C26—H26 | 119.4 |
C9—C8—H8 | 120.1 | C26—C27—C28 | 120.03 (17) |
C7—C8—H8 | 120.1 | C26—C27—H27 | 120.0 |
C8—C9—C10 | 120.45 (16) | C28—C27—H27 | 120.0 |
C8—C9—H9 | 119.8 | C29—C28—C27 | 120.02 (18) |
C10—C9—H9 | 119.8 | C29—C28—H28 | 120.0 |
C9—C10—C5 | 119.64 (14) | C27—C28—H28 | 120.0 |
C9—C10—C1 | 120.94 (14) | C28—C29—C30 | 120.82 (17) |
C5—C10—C1 | 119.41 (14) | C28—C29—H29 | 119.6 |
C1—N1—N2 | 117.98 (13) | C30—C29—H29 | 119.6 |
C11—N2—N1 | 119.22 (14) | C29—C30—C25 | 118.97 (15) |
C11—N2—H2 | 117.8 (13) | C29—C30—C21 | 120.96 (14) |
N1—N2—H2 | 123.0 (13) | C25—C30—C21 | 120.07 (14) |
N3—C11—N2 | 115.75 (14) | C21—N21—N22 | 117.99 (13) |
N3—C11—S1 | 124.70 (12) | C31—N22—N21 | 118.72 (14) |
N2—C11—S1 | 119.54 (13) | C31—N22—H22 | 115.9 (14) |
C11—N3—C12 | 124.39 (15) | N21—N22—H22 | 123.3 (14) |
C11—N3—H3 | 117.7 (14) | N23—C31—N22 | 115.30 (16) |
C12—N3—H3 | 117.9 (14) | N23—C31—S21 | 124.95 (13) |
N3—C12—H12A | 109.5 | N22—C31—S21 | 119.74 (13) |
N3—C12—H12B | 109.5 | C31—N23—C32 | 123.87 (18) |
H12A—C12—H12B | 109.5 | C31—N23—H23 | 120.0 (15) |
N3—C12—H12C | 109.5 | C32—N23—H23 | 116.0 (15) |
H12A—C12—H12C | 109.5 | N23—C32—H32A | 109.5 |
H12B—C12—H12C | 109.5 | N23—C32—H32B | 109.5 |
N3—C12—H12D | 109.5 | H32A—C32—H32B | 109.5 |
N3—C12—H12E | 109.5 | N23—C32—H32C | 109.5 |
H12D—C12—H12E | 109.5 | H32A—C32—H32C | 109.5 |
N3—C12—H12F | 109.5 | H32B—C32—H32C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···S21i | 0.88 (2) | 3.03 (2) | 3.7226 (15) | 138.0 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···S21i | 0.88 (2) | 3.03 (2) | 3.7226 (15) | 138.0 |
Symmetry code: (i) −x+1, −y+1, −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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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.
Thiosemicarbazone derivatives have been used as ligands in coordination chemistry as well as for applications in biological systems, because some of them shows antifungal, antibacterial and anticancer properties (Lobana et al., 2009). As part of our study on thiosemicarbazone compounds, we report herein the crystal structure of a tetralone thiosemicarbazone derivative.
In the crystal structure of the title compound, there are two crystallographically independent molecules on the asymmetric unit in general positions, in which some of the C, and H atoms are disordered (Fig. 1). For one crystallographic independent molecule, the dihedral angle between the benzene ring (C5—C10) and the N1—N2—C11—N3 fragment amounts to 12.92 (14)° and for the second crystallographically independent molecule the dihedral angle between the benzene ring (C25—C30) and the N21—N22—C31—N23 fragment amouts to 7.60 (13)°. So, the molecules do not only show a different kind of disorder, but differ also in the molecular geometry.
In the crystal, the molecules are linked by long weak N—H···S hydrogen bonding into chains that run along the a-axis. The S···H distances amount to 3.02 (2) Å for the S1 and 3.291 (22) Å for the S21 atoms (Table 1). When viewed along the c-axis (Fig. 2), the molecules show a herringbone motif.