Synthesis, crystal structure and Hirshfeld analysis of N-ethyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclo­pent-2-en-1-yl­idene}hydrazinecarbo­thio­amide

Oliveira, A.B. de; Beck, J.; Daniels, J.

doi:10.1107/S2056989024002913

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ISSN: 2056-9890

Volume 80| Part 5| May 2024| Pages 452-458

https://doi.org/10.1107/S2056989024002913

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Synthesis, crystal structure and Hirshfeld analysis of N-ethyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide

Adriano Bof de Oliveira,^a ^* Johannes Beck ^b and Jörg Daniels ^b

^aDepartamento de Química, Universidade Federal de Sergipe, Av. Marcelo Deda Chagas s/n, Campus Universitário, 49107-230 São Cristóvão-SE, Brazil, and ^bInstitut für Anorganische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany
^*Correspondence e-mail: adriano@daad-alumni.de

Edited by C. Schulzke, Universität Greifswald, Germany (Received 20 March 2024; accepted 2 April 2024; online 9 April 2024)

The title compound (C₁₄H₂₃N₃S, common name: cis-jasmone 4-ethylthiosemicarbazone) was synthesized by the equimolar reaction of cis-jasmone and 4-ethylthiosemicarbazide in ethanol facilitated by acid catalysis. There is one crystallographically independent molecule in the asymmetric unit, which shows disorder of the terminal ethyl group of the jasmone carbon chain [site-occupancy ratio = 0.911 (5):0.089 (5)]. The thiosemicarbazone entity [N—N—C(=S)—N] is approximately planar, with the maximum deviation of the mean plane through the N/N/C/S/N atoms being 0.0331 (8) Å, while the maximum deviation of the mean plane through the five-membered ring of the jasmone fragment amounts to −0.0337 (8) Å. The dihedral angle between the two planes is 4.98 (7)°. The molecule is not planar due to this structural feature and the sp³-hybridized atoms of the jasmone carbon chain. Additionally, one H⋯N intramolecular interaction is observed, with graph-set motif S(5). In the crystal, the molecules are connected through pairs of H⋯S interactions with R₂²(8) and R₂¹(7) graph-set motifs into centrosymmetric dimers. The dimers are further connected by H⋯N interactions with graph-set motif R₂²(12), which are related by an inversion centre, forming a mono-periodic hydrogen-bonded ribbon parallel to the b-axis. The crystal structure and the supramolecular assembly of the title compound are compared with four known cis-jasmone thiosemicarbazone derivatives (two crystalline modifications of the non-substituted form, the 4-methyl and the 4-phenyl derivatives). A Hirshfeld surface analysis indicates that the major contributions for the crystal cohesion are from H⋯H (70.7%), H⋯S/S⋯H (13.5%), H⋯C/C⋯H (8.8%), and H⋯N/N⋯H (6.6%) interfaces (only the disordered atoms with the highest s.o.f. were considered for the evaluation).

Keywords: thiosemicarbazone; jasmone; jasmone 4-ethylthiosemicarbazone; H-bonded ribbon; crystal structure; Hirshfeld analysis.

CCDC reference: 2304271

1. Chemical context

Thiosemicarbazones [R₁R₂C=N—N(H)C(=S)NR₃R₄] can be readily prepared through a well-known condensation reaction between a ketone or an aldehyde (R₁R₂C=O) and a thiosemicarbazide derivative [H₂N—N(H)C(=S)NR₃R₄] (Freund & Schander, 1902 ). Due to the structural diversity of the educts, a huge number of thiosemicarbazone derivatives (TSC) can be synthesized for numerous applications across a wide range of scientific disciplines, such as coordination chemistry, medicinal chemistry and materials science. These three main approaches are interconnected, as demonstrated by Farias et al. (2021 ) in a report concerning the synthesis, in vitro and in silico evaluations of the antitumor activities of two thiosemicarbazone Ni^II complexes, which were considered materials with biological properties. The coordination chemistry of thiosemicarbazone derivatives was addressed in a review by Lobana et al. (2009 ), illustrating the chemical bonding of TSCs with metal centres of different Lewis acidity, the coordination modes and geometries, and some biological and analytical applications.

Several thiosemicarbazone derivatives have biological properties either as metal complexes or as non-coordinated molecules. For examples of thiosemicarbazone complexes with biological activity, see: Gupta et al. (2022 ); Khan et al. (2022 ); Monsur Showkot Hossain et al. (2023 ); Parrilha et al. (2022 ), which covers compounds for chemotherapy and medical diagnostic imaging combined, also referred to as theranostics, and Singh et al. (2023 ). For a review of TSC complexes in the inhibition of topoisomerases, which are biological targets of prime importance in cancer research, see: Jiang et al. (2023 ). For examples of the biological activity of non-coordinated thiosemicarbazone derivatives, see: Fatondji et al. (2013 ), which shows a small chemical library with 35 derivatives with trypanocidal activity against the Trypanosoma brucei brucei parasite, and for a review on tyrosinase inhibitory activity, which is another important biological target, see: Hałdys & Latajka (2019 ). The non-coordinated TSCs are also mentioned in a review on tyrosinase inhibition by Zolghadri et al. (2019 ). In addition, thiosemicarbazone derivatives have been studied for the treatment of Parkinson's disease (Mathew et al., 2021 ), microbial growth inhibition (D'Agostino et al., 2022 ), anti-inflammatory pathologies (Kanso et al., 2021 ) and antifungal activity (Bajaj et al., 2021 ). Specifically, in the context of this work, the parent cis-jasmone thiosemicarbazone derivative has shown fungistatic biological activity as a free molecule (Jamiołkowska et al., 2022 ) and also as a Cu^II complex (Orsoni et al., 2020 ).

In materials science, thiosemicarbazone complexes are employed as single-source educts for the synthesis of nanostructured materials, e.g., CdS nanocrystals (Masikane et al., 2019 ) and nanostructured CuFeS₂, which is being used as an electrode material for supercapacitors (Ansari et al., 2022 ). Non-coordinated thiosemicarbazones have been used to functionalize metal–organic frameworks (MOFs), such as zeolitic imidazolate frameworks (mainly, ZIF-8), for the removal of Hg^II from aqueous solutions at room temperature and neutral pH (Jaafar et al., 2021 ). TSC derivatives have also been studied as corrosion inhibitors for metals and alloys. For the respective theoretical approach, see: Silva & Martínez-Huitle (2021 ). Additionally, thiosemicarbazone derivatives have turned out to be useful in several fields of analytical chemistry, including calorimetry, fluorimetry and electrochemical sensors, e.g., in the detection of anions and metallic cations (Özbek & Berkel, 2023 ).

In this context and as a contribution to the TSC chemistry, we report here the synthesis, crystal structure and Hirshfeld analysis of cis-jasmone 4-ethylthiosemicarbazone.

2. Structural commentary

For the title compound, cis-jasmone 4-ethylthiosemicarbazone (JETSC), the asymmetric unit consists of one molecule with all atoms in general positions, which shows disorder over the jasmone carbon chain [s.o.f. = 0.911 (5):0.089 (5)]. The disordered atoms with higher s.o.f. are A-labelled and the atoms with lower s.o.f. are B-labelled (Fig. 1). The thiosemicarbazone entity is approximately planar, with the maximum deviation of the mean plane through the N1/N2/C12/S1 atoms being 0.0331 (8) Å for N2 (r.m.s.d. = 0.0215 Å). For the five-membered ring of the jasmone fragment, the maximum deviation of the mean plane through the selected atoms amounts to −0.0337 (8) Å for C2 (r.m.s.d. = 0.0256 Å) and the dihedral angle between the two planes is 4.98 (7)°. The molecule is not planar due to this angle and to the sp³-hybridized atoms of the jasmone carbon chain, with the torsion angles for the C5—C6—C7—C8, C7—C8—C9A—C10A and C7—C8— C9B—C10B fragments being −138.74 (16), −106.5 (2) and 132.7 (10)°. Finally, an intramolecular hydrogen-bond interaction is observed, N3—H3⋯N1, which forms a ring of graph-set motif S(5) (Fig. 1 and Table 1). For a review addressing hydrogen bonding in the solid state, see: Steiner (2002 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1ⁱ	0.873 (18)	2.608 (18)	3.4808 (12)	177.6 (15)
N3—H3⋯N1	0.828 (16)	2.187 (15)	2.6008 (15)	111.0 (13)
C2—H2A⋯S1ⁱ	1.003 (16)	2.822 (15)	3.3535 (13)	113.7 (10)
C13—H13B⋯N1ⁱⁱ	0.966 (15)	2.655 (15)	3.5466 (17)	153.5 (12)
Symmetry codes: (i) ; (ii) .

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 40% probability level. Disordered atoms are drawn with 40% transparency and labelled C9A/C10A [s.o.f. = 0.911 (5)] and C9B/C10B [s.o.f. = 0.089 (5)]. For the N3—H3⋯N1 intramolecular interaction, a ring with graph-set motif S(5) is observed.

3. Supramolecular features

In the crystal, the molecules are connected through H⋯S and H⋯N interactions, forming rings of graph-set motifs R₂²(8), R₂¹(7) and R₂²(12) for the C₂H₂N₂S₂, C₂H₂N₂S and C₄H₂N₆ entities, respectively (Fig. 2). The S1 and N1 atoms act as double hydrogen-bond acceptors, where the N1 atoms play an important role in the supramolecular arrangement of the molecules. Firstly, the molecules are connected into centrosymmetric dimers through C2—H2A⋯S1ⁱ and N2—H2⋯S1ⁱ intermolecular interactions [symmetry code: (i) −x + 1, −y, −z + 1], as has also been observed in other cis-jasmone thiosemicarbazone derivatives (Oliveira et al., 2023a , 2024 ). These centrosymmetric dimers, in which rings of graph-set motif R₂²(8) and R₂¹(7) are present, have their centres of gravity located in the centre of the ac planes. In addition, the dimers are further connected by C13—H13B⋯N1ⁱⁱ intermolecular interactions [symmetry code: (ii) −x + 1, −y + 1, −z + 1], where rings of graph-set motif R₂²(12) are observed (Fig. 2, Table 1). The centre of gravity of the centrosymmetric C₄H₂N₆ ring lies at an inversion centre of the cell and thus, the molecules are linked into a mono-periodic hydrogen-bonded ribbon parallel to the b-axis. (Fig. 3).

Figure 2
Crystal structure section of the title compound showing the intermolecular hydrogen-bonding interactions as dashed lines. The molecules are linked via pairs of C2—H2A⋯S1ⁱ, N—H2⋯S1ⁱ and C13—H13B—N1ⁱⁱ interactions with graph-set motifs R₂²(8), R₂¹(7) and R₂²(12). [Symmetry codes: (i) −x + 1, −y, −z + 1; (ii) −x + 1, −y + 1, −z + 1.]

Figure 3
Crystal structure section of the title compound, showing the intermolecular hydrogen-bonded interactions as dashed lines. Disorder is not shown for clarity. The molecules are linked into mono-periodic hydrogen-bonded ribbons parallel to the b-axis via pairs of N—H⋯S, C—H⋯S and C—H⋯N interactions with graph-set motifs R₂²(8), R₂¹(7) and R₂²(12).

The Hirshfeld surface analysis (Hirshfeld, 1977 ), the graphical representations and the two-dimensional Hirshfeld surface fingerprint plots (HSFP) were calculated with the Crystal Explorer software (Wolff et al., 2012 ) and only the atoms with the higher s.o.f. were taken into account. The Hirshfeld surface analysis of the title compound suggests that the most relevant intermolecular interactions for the crystal packing are H⋯H (70.7%), H⋯S/S⋯H (13.5%), H⋯C/C⋯H (8.8%) and H ⋯N/N⋯H (6.4%). The graphical representation of the Hirshfeld surface (d_norm) is given in a figure with transparency and using the ball-and-stick model. Locations of the strongest intermolecular contacts, i.e, the regions around the H2, H2A and S1 atoms are indicated in red (Fig. 4). These atoms are those involved in the H⋯S interactions shown in previous figures (Figs. 2 and 3). The contributions to the crystal cohesion are represented as two-dimensional Hirshfeld surface fingerprint plots (HSFP) with coloured dots (Fig. 5). The d_i (x-axis) and the d_e (y-axis) values are the closest internal and external distances from given points on the Hirshfeld surface contacts (in Å).

Figure 4
Hirshfeld surface graphical representation (d_norm) for the title compound. The surface is drawn with transparency, the molecules are drawn in ball and stick model and the disorder is not shown for clarity. The regions with strongest intermolecular interactions are shown in red.

Figure 5
The Hirshfeld surface two-dimensional fingerprint plot (HSFP) for the title compound, showing the contacts in detail (coloured). The major contributions of the interactions to the crystal cohesion amount to (a) H⋯H (70.7%), (b) H⋯S/S⋯H (13.5%), (c) H⋯C/C⋯H (8.8%) and (d) H⋯N/N⋯H (6.4%). The d_i (x-axis) and the d_e (y-axis) values are the closest internal and external distances from given points on the Hirshfeld surface contacts (in Å). Regarding the disorder, only the atoms with the highest s.o.f. were considered.

4. Database survey

To the best of our knowledge and from using database tools such as the Cambridge Structural Database (CSD, accessed via WebCSD on March 15, 2024; Groom et al., 2016 ), there are four crystal structures of cis-jasmone thiosemicarbazone derivatives reported in the literature: the α-crystalline modification of cis-jasmone thiosemicarbazone, α-JTSC (refcode ZAJRUB; Orsoni et al., 2020), the β-crystalline modification, β-JTSC (ZAJRUB01; Oliveira et al., 2023b ), cis-jasmone 4-methylthiosemicarbazone, JMTSC (JOFYOW; Oliveira et al., 2024), cis-jasmone 4-phenylthiosemicarbazone, JPTSC (QIVYIH; Oliveira et al., 2023a), with cis-jasmone 4-ethylthiosemicarbazone, JETSC (this work) being the fifth. For the Hirshfeld analysis comparison, of the α-JTSC and the β-JTSC crystalline modifications, only β-JTSC was considered and will be designated in the following merely as JTSC. Fig. 6 provides the chemical structures of JTSC, JMTSC, JETSC and JPTSC. The Hirshfeld surface fingerprint signatures of the TSC derivatives are drawn as two-dimensional plots (HSFP) and the most relevant contribution for the crystal packing, the H⋯H intermolecular interactions, are highlighted (coloured) (Fig. 7). Their contributions for the crystal cohesion are 67.8% for JTSC, 70.6% for JMTSC, 70.7% for the title compound, JETSC, and 65.3% for JPTSC. It might be argued that the methyl and ethyl derivatives show more C—H entities for H⋯H intermolecular interactions in comparison to the non-substituted JTSC, and less steric hindrance than the phenyl derivative JPTSC. These structural features would explain the higher values of the H⋯H contributions to the crystal packing for JMTSC and JETSC, and the lower contributions for JTSC and JPTSC. In addition, the H⋯N/N⋯H contacts, which are important for the supramolecular arrangement of JETSC (this work) are clearly represented in the HSFP signature of the crystal structure and do not appear in the same way in the signature of the related compounds (Fig. 8). Although the contributions of the H⋯N/N⋯H contacts to the crystal packing for all the jasmone thiosemicarbazone derivatives are very similar in value, within a range of 4.9% to 6.4%, the H⋯N intermolecular interactions are of major importance for the molecular assembly of JETSC, as shown in Figs. 2 and 3.

Figure 6
Chemical structure formulae of (a) cis-jasmone thiosemicarbazone, JTSC, (b) cis-jasmone 4-methylthiosemicarbazone, JMTSC, (c) cis-jasmone 4-ethylthiosemicarbazone, JETSC, and (d) cis-jasmone 4-phenylthiosemicarbazone, JPTSC.

Figure 7
The Hirshfeld surface two-dimensional fingerprint plot (HSFP) signatures for (a) JTSC (Oliveira et al., 2023b

), (b) JMTSC (Oliveira et al., 2024

), (c) JETSC (this work) and (d) JPTSC (Oliveira et al., 2023a

). The major contributions for the crystal cohesion in all structures are the H⋯H intermolecular interactions, which amount to 67.8%, 70.6%, 70.7% and 65.3%, respectively, and are highlighted (coloured). The d_i (x-axis) and the d_e (y-axis) values are the closest internal and external distances from given points on the Hirshfeld surface contacts (in Å). Regarding the disorder, only the atoms with the highest s.o.f. were considered.

Figure 8
The Hirshfeld surface two-dimensional fingerprint plot (HSFP) signatures for (a) JTSC (Oliveira et al., 2023b

), (b) JMTSC (Oliveira et al., 2024

), (c) JETSC (this work) and (d) JPTSC (Oliveira et al., 2023a

), with the H⋯N/N⋯H contacts highlighted (coloured). The d_i (x-axis) and the d_e (y-axis) values are the closest internal and external distances from given points on the Hirshfeld surface contacts (in Å). Regarding the disorder, only the atoms with the highest s.o.f. were considered.

The influence of the substituent at the terminal N atom on the supramolecular assembly in the crystal structures of jasmone TSC derivatives is shown in Figs. 9 and 10. For the non-substituted α- and β-crystalline modifications of cis-jasmone thiosemicarbazone, α-JTSC (Orsoni et al., 2020) and β-JTSC (Oliveira et al., 2023b), the molecules are connected via pairs of H⋯S interactions into mono-periodic hydrogen-bonded ribbons. The crystal structure of α-JTSC shows three crystallographically independent molecules in the asymmetric unit. The molecules are linked by H⋯S interactions with graph-set motif R₂²(8) along [100] into two independent one-dimensional hydrogen-bonded polymers (Fig. 9a). For β-JTSC, with one crystallographically independent molecule in the asymmetric unit, the molecules are connected by H⋯S interactions with graph-set motifs R₂²(8) and R₂¹(7) into mono-periodic hydrogen-bonded ribbons along [010] (Fig. 9b). For the supramolecular assembly of cis-jasmone 4-methylthiosemicarbazone, JMTSC, (Oliveira et al., 2024) and of cis-jasmone 4-phenylthiosemicarbazone, JPTSC, (Oliveira et al., 2023a), a structural similarity can be observed. In the crystal, the molecules are linked into centrosymmetric dimers by pairs of H⋯S interactions, in which rings of graph-set motifs R₂²(8) and R₂¹(7) are present. As a result of the steric hindrance of the methyl and phenyl groups, respectively, the dimers are assembled as discrete units and only weak intermolecular interactions, viz., London dispersion forces can be assumed (Fig. 10a,b). The C—H⋯N intermolecular interactions observed in the crystal structure of the title compound, which cause the increase of the supramolecular dimensionality, are not observed in any of the four crystal structures of closely related molecules mentioned above.

Figure 9
(a) Section of the molecular arrangement of α-JTSC (Orsoni et al., 2020

). The three crystallographically independent molecules are A-, B-, and C-labelled. They are linked by pairs of N—H⋯S interactions, with rings of graph-set motif R₂²(8), into two independent mono-periodic hydrogen-bonded ribbons along [100]. [Symmetry codes: (i) x + 1, y, z; (ii) x − 1, y, z; (iii) −x + 1, −y, −z + 1; (iv) −x, −y, −z + 1.] (b) Section of the molecular arrangement of β-JTSC (Oliveira et al., 2023b

). The molecules are connected by pairs of N—H⋯S and C—H⋯S intermolecular interactions, with rings of graph-set motifs R₂²(8) and R₂¹(7), into mono-periodic hydrogen-bonded ribbons along [010]. Disorder is not shown for clarity. [Symmetry codes: (i) −x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) −x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ .]

Figure 10
(a) Graphical representation of the JMTSC dimeric arrangement. The molecules are connected by pairs of N—H⋯S and C—H⋯S intermolecular interactions, with rings of graph-set motifs R₂²(8) and R₂¹(7), into centrosymmetric dimers. Only the non-disordered JMTSC-1 dimer is drawn for clarity (Oliveira et al., 2024

). [Symmetry code: (i) −x, −y, −z + 2]. (b) Graphical representation of the JPTSC dimeric arrangement (Oliveira et al., 2023a

). The molecules are linked also via pairs of N—H⋯S and C—H⋯S intermolecular interactions, with rings of graph-set motifs R₂²(8) and R₂¹(7), into centrosymmetric dimers. One N—H⋯N intramolecular interaction of graph-set S(5) is observed. [Symmetry code: (i) −x + 1, −y, −z.]

5. Synthesis and crystallization

The starting materials are commercially available and were used without further purification. The synthesis of the cis-jasmone 4-ethylthiosemicarbazone derivative was adapted from previously reported procedures (Freund & Schander, 1902; Oliveira et al., 2024; Orsoni et al., 2020). cis-Jasmone was dissolved in ethanol under magnetic stirring at room temperature (8 mmol, 1.3139 g, in 50 mL). A solution of 4-ethylthiosemicarbazide in ethanol (8 mmol, 0.9535 g, in 50 mL) was prepared under the same conditions. The solutions were combined, the HCl catalyst was added (1 mL, 1 M), and the final mixture was refluxed under magnetic stirring for 8 h. After cooling, the precipitated product was filtered off and washed with cold ethanol. Yield = 0.7431 g (35%). Colourless single crystals suitable for X-ray diffraction were obtained from tetrahydrofuran by slow evaporation of the solvent at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. There is one crystallographically independent molecule in the asymmetric unit of the title compound, which shows disorder over the chain of the cis-jasmone fragment, viz., the C9 and C10 atoms [Fig. 1; site-occupancy ratio = 0.911 (5):0.089 (5)]. The H atoms were refined freely, with exception of those bonded to C9B and C10B. These constrained H atoms were located in a difference-Fourier map, but were positioned with idealized geometry and refined isotropically using a riding model. For the H atoms attached to atom C9B with U_iso(H) = 1.2 U_eq(C), the C—H bonds were set to 0.97 Å. For the C10B atom, the methyl H atoms were allowed to rotate but not to tip to best fit the experimental electron density, with U_iso(H) = 1.5 U_eq(C), and the C—H bonds were set to 0.96 Å.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₂₃N₃S
M_r	265.41
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	123
a, b, c (Å)	7.4584 (2), 7.7429 (3), 13.2461 (3)
α, β, γ (°)	103.025 (2), 98.735 (2), 90.769 (2)
V (Å³)	735.73 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Enraf–Nonius FR590 Kappa CCD
Absorption correction	Analytical (using the de Meulenaer & Tompa algorithm; Alcock, 1970 )
T_min, T_max	0.944, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	13116, 3325, 2810
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.085, 1.02
No. of reflections	3325
No. of parameters	275
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21
Computer programs: COLLECT (Nonius, 1998 ), HKL, DENZO and SCALEPACK (Otwinowski & Minor, 1997 ), SIR92 (Altomare et al., 1994 ), SHELXL2018/3 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2006 ), CrystalExplorer (Wolff et al., 2012), WinGX (Farrugia, 2012 ), publCIF (Westrip, 2010 ) and enCIFer (Allen et al., 2004 ).

Supporting information

CCDC reference: 2304271

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024002913/yz2054sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024002913/yz2054Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024002913/yz2054Isup3.cml

checkCIF report

Computing details top

N-Ethyl-2-{3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-ylidene}hydrazinecarbothioamide top

Crystal data top

C₁₄H₂₃N₃S	Z = 2
M_r = 265.41	F(000) = 288
Triclinic, P1	D_x = 1.198 Mg m⁻³
a = 7.4584 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7429 (3) Å	Cell parameters from 27549 reflections
c = 13.2461 (3) Å	θ = 2.9–27.5°
α = 103.025 (2)°	µ = 0.21 mm⁻¹
β = 98.735 (2)°	T = 123 K
γ = 90.769 (2)°	Fragment, colourless
V = 735.73 (4) Å³	0.30 × 0.20 × 0.05 mm

Data collection top

Enraf–Nonius FR590 Kappa CCD diffractometer	3325 independent reflections
Radiation source: sealed X-ray tube, Enraf Nonius FR590	2810 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.047
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD rotation images, thick slices, κ–goniostat scans	h = −9→9
Absorption correction: analytical (using the de Meulenaer & Tompa algorithm; Alcock, 1970)	k = −10→10
T_min = 0.944, T_max = 0.990	l = −17→17
13116 measured reflections

Refinement top

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)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0336P)² + 0.2782P] where P = (F_o² + 2F_c²)/3
3325 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.87223 (16)	0.34727 (16)	0.71554 (9)	0.0198 (3)
C2	0.95725 (17)	0.17051 (17)	0.68820 (10)	0.0224 (3)
C3	1.14804 (18)	0.20144 (18)	0.75527 (11)	0.0243 (3)
C4	1.16282 (17)	0.39689 (17)	0.80623 (10)	0.0217 (3)
C5	1.00677 (16)	0.47688 (17)	0.78541 (9)	0.0207 (3)
C6	0.96603 (18)	0.66839 (18)	0.82233 (11)	0.0246 (3)
C7	0.8584 (2)	0.69971 (19)	0.91194 (11)	0.0304 (3)
C8	0.7226 (2)	0.8050 (2)	0.92470 (12)	0.0328 (3)
C9A	0.6346 (2)	0.9092 (3)	0.84930 (14)	0.0342 (5)	0.911 (5)
C10A	0.6880 (4)	1.1062 (3)	0.8879 (2)	0.0465 (6)	0.911 (5)
H9A	0.500 (3)	0.894 (3)	0.8412 (16)	0.050 (6)*	0.911 (5)
H9B	0.666 (2)	0.859 (2)	0.7779 (15)	0.036 (5)*	0.911 (5)
H10A	0.823 (3)	1.124 (3)	0.8960 (16)	0.048 (6)*	0.911 (5)
H10B	0.625 (3)	1.173 (3)	0.837 (2)	0.065 (7)*	0.911 (5)
H10C	0.655 (3)	1.149 (3)	0.959 (2)	0.063 (7)*	0.911 (5)
C9B	0.778 (3)	1.006 (2)	0.9103 (13)	0.033 (5)	0.089 (5)
H9C	0.794526	1.092924	0.976673	0.039*	0.089 (5)
H9D	0.886258	1.005830	0.878229	0.039*	0.089 (5)
C10B	0.614 (3)	1.036 (3)	0.839 (2)	0.042 (6)	0.089 (5)
H10D	0.595042	0.941005	0.777614	0.064*	0.089 (5)
H10E	0.630332	1.146535	0.819865	0.064*	0.089 (5)
H10F	0.510340	1.040027	0.874748	0.064*	0.089 (5)
C11	1.33750 (18)	0.4800 (2)	0.87064 (12)	0.0284 (3)
C12	0.43231 (16)	0.31557 (17)	0.57148 (10)	0.0203 (3)
C13	0.22713 (17)	0.56201 (18)	0.56951 (11)	0.0226 (3)
C14	0.2314 (2)	0.75737 (19)	0.62214 (12)	0.0279 (3)
H2	0.627 (2)	0.157 (2)	0.5899 (13)	0.037 (5)*
H3	0.477 (2)	0.548 (2)	0.6476 (12)	0.026 (4)*
H2A	0.883 (2)	0.072 (2)	0.7024 (12)	0.029 (4)*
H2B	0.967 (2)	0.139 (2)	0.6138 (13)	0.028 (4)*
H3A	1.243 (2)	0.167 (2)	0.7122 (12)	0.030 (4)*
H3B	1.163 (2)	0.132 (2)	0.8094 (12)	0.029 (4)*
H6A	0.900 (2)	0.712 (2)	0.7621 (12)	0.028 (4)*
H6B	1.081 (2)	0.739 (2)	0.8457 (12)	0.033 (4)*
H7	0.899 (3)	0.636 (3)	0.9680 (15)	0.054 (5)*
H8	0.670 (2)	0.817 (2)	0.9901 (14)	0.040 (5)*
H11A	1.438 (3)	0.449 (2)	0.8318 (14)	0.045 (5)*
H11B	1.335 (2)	0.609 (3)	0.8935 (14)	0.046 (5)*
H11C	1.366 (3)	0.434 (3)	0.9314 (15)	0.051 (5)*
H13A	0.127 (2)	0.4975 (19)	0.5857 (11)	0.021 (3)*
H13B	0.211 (2)	0.5436 (19)	0.4940 (12)	0.024 (4)*
H14A	0.244 (2)	0.775 (2)	0.6981 (13)	0.032 (4)*
H14B	0.332 (2)	0.821 (2)	0.6068 (13)	0.035 (4)*
H14C	0.118 (2)	0.805 (2)	0.5956 (13)	0.038 (4)*
N1	0.71169 (14)	0.39345 (14)	0.68391 (8)	0.0214 (2)
N2	0.59457 (14)	0.26386 (15)	0.61441 (9)	0.0222 (2)
N3	0.39593 (14)	0.48485 (15)	0.60530 (9)	0.0217 (2)
S1	0.28777 (4)	0.16924 (4)	0.48084 (3)	0.02554 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0176 (6)	0.0227 (6)	0.0190 (6)	−0.0003 (5)	0.0017 (5)	0.0055 (5)
C2	0.0184 (6)	0.0233 (6)	0.0231 (7)	−0.0006 (5)	−0.0009 (5)	0.0031 (5)
C3	0.0187 (6)	0.0257 (7)	0.0261 (7)	0.0019 (5)	−0.0009 (5)	0.0039 (5)
C4	0.0192 (6)	0.0255 (6)	0.0196 (6)	−0.0020 (5)	0.0005 (5)	0.0052 (5)
C5	0.0199 (6)	0.0226 (6)	0.0189 (6)	−0.0021 (5)	0.0019 (5)	0.0047 (5)
C6	0.0225 (6)	0.0222 (6)	0.0277 (7)	−0.0017 (5)	0.0010 (5)	0.0048 (5)
C7	0.0354 (8)	0.0288 (7)	0.0275 (7)	0.0040 (6)	0.0050 (6)	0.0075 (6)
C8	0.0354 (8)	0.0311 (8)	0.0325 (8)	0.0031 (6)	0.0095 (6)	0.0058 (6)
C9A	0.0276 (9)	0.0372 (12)	0.0351 (10)	0.0066 (7)	0.0011 (7)	0.0050 (8)
C10A	0.0618 (16)	0.0311 (12)	0.0514 (15)	0.0110 (11)	0.0225 (12)	0.0099 (10)
C9B	0.046 (10)	0.017 (8)	0.032 (9)	0.012 (7)	0.010 (7)	−0.003 (6)
C10B	0.048 (13)	0.037 (14)	0.054 (14)	0.011 (11)	0.043 (12)	0.010 (11)
C11	0.0203 (7)	0.0318 (8)	0.0291 (8)	−0.0025 (6)	−0.0040 (6)	0.0041 (6)
C12	0.0163 (6)	0.0234 (6)	0.0217 (6)	−0.0009 (5)	0.0021 (5)	0.0068 (5)
C13	0.0173 (6)	0.0263 (7)	0.0236 (7)	0.0016 (5)	−0.0003 (5)	0.0070 (5)
C14	0.0239 (7)	0.0276 (7)	0.0306 (8)	0.0051 (6)	0.0024 (6)	0.0043 (6)
N1	0.0184 (5)	0.0227 (5)	0.0212 (5)	−0.0025 (4)	−0.0009 (4)	0.0042 (4)
N2	0.0169 (5)	0.0204 (6)	0.0258 (6)	−0.0002 (4)	−0.0027 (4)	0.0023 (4)
N3	0.0161 (5)	0.0222 (5)	0.0234 (6)	−0.0003 (4)	−0.0028 (4)	0.0021 (4)
S1	0.01824 (16)	0.02307 (18)	0.03029 (19)	−0.00124 (12)	−0.00422 (12)	0.00120 (13)

Geometric parameters (Å, º) top

C1—N1	1.2899 (16)	C10A—H10B	1.01 (3)
C1—C5	1.4639 (17)	C10A—H10C	0.99 (2)
C1—C2	1.5086 (18)	C9B—C10B	1.48 (3)
C2—C3	1.5436 (17)	C9B—H9C	0.9700
C2—H2A	1.003 (16)	C9B—H9D	0.9700
C2—H2B	0.974 (16)	C10B—H10D	0.9600
C3—C4	1.5068 (18)	C10B—H10E	0.9600
C3—H3A	0.977 (16)	C10B—H10F	0.9600
C3—H3B	0.980 (16)	C11—H11A	0.973 (19)
C4—C5	1.3465 (17)	C11—H11B	0.98 (2)
C4—C11	1.4939 (18)	C11—H11C	0.95 (2)
C5—C6	1.5035 (18)	C12—N3	1.3319 (17)
C6—C7	1.509 (2)	C12—N2	1.3620 (16)
C6—H6A	0.998 (16)	C12—S1	1.6877 (13)
C6—H6B	0.980 (17)	C13—N3	1.4606 (16)
C7—C8	1.316 (2)	C13—C14	1.5139 (19)
C7—H7	0.99 (2)	C13—H13A	0.971 (15)
C8—C9A	1.502 (2)	C13—H13B	0.966 (15)
C8—C9B	1.661 (17)	C14—H14A	0.975 (17)
C8—H8	0.992 (18)	C14—H14B	0.963 (17)
C9A—C10A	1.522 (3)	C14—H14C	0.973 (18)
C9A—H9A	0.99 (2)	N1—N2	1.3904 (15)
C9A—H9B	1.00 (2)	N2—H2	0.873 (18)
C10A—H10A	1.00 (2)	N3—H3	0.828 (16)

N1—C1—C5	120.80 (11)	C9A—C10A—H10C	109.0 (14)
N1—C1—C2	129.87 (11)	H10A—C10A—H10C	106.4 (18)
C5—C1—C2	109.28 (10)	H10B—C10A—H10C	111 (2)
C1—C2—C3	103.99 (10)	C10B—C9B—C8	100.0 (14)
C1—C2—H2A	111.9 (9)	C10B—C9B—H9C	111.8
C3—C2—H2A	113.2 (9)	C8—C9B—H9C	111.8
C1—C2—H2B	110.7 (9)	C10B—C9B—H9D	111.8
C3—C2—H2B	110.4 (9)	C8—C9B—H9D	111.8
H2A—C2—H2B	106.7 (12)	H9C—C9B—H9D	109.5
C4—C3—C2	104.68 (10)	C9B—C10B—H10D	109.5
C4—C3—H3A	112.1 (9)	C9B—C10B—H10E	109.5
C2—C3—H3A	111.3 (9)	H10D—C10B—H10E	109.5
C4—C3—H3B	109.8 (9)	C9B—C10B—H10F	109.5
C2—C3—H3B	112.2 (9)	H10D—C10B—H10F	109.5
H3A—C3—H3B	106.8 (13)	H10E—C10B—H10F	109.5
C5—C4—C11	127.60 (12)	C4—C11—H11A	110.2 (11)
C5—C4—C3	112.28 (11)	C4—C11—H11B	112.8 (11)
C11—C4—C3	120.11 (11)	H11A—C11—H11B	110.0 (15)
C4—C5—C1	109.42 (11)	C4—C11—H11C	110.6 (12)
C4—C5—C6	128.51 (12)	H11A—C11—H11C	105.0 (15)
C1—C5—C6	122.06 (11)	H11B—C11—H11C	107.9 (15)
C5—C6—C7	113.14 (11)	N3—C12—N2	116.44 (11)
C5—C6—H6A	109.4 (9)	N3—C12—S1	122.95 (10)
C7—C6—H6A	110.4 (9)	N2—C12—S1	120.61 (10)
C5—C6—H6B	108.9 (9)	N3—C13—C14	110.15 (11)
C7—C6—H6B	108.3 (9)	N3—C13—H13A	108.2 (8)
H6A—C6—H6B	106.6 (13)	C14—C13—H13A	111.2 (9)
C8—C7—C6	127.15 (14)	N3—C13—H13B	109.0 (9)
C8—C7—H7	117.6 (11)	C14—C13—H13B	111.4 (9)
C6—C7—H7	115.2 (11)	H13A—C13—H13B	106.7 (12)
C7—C8—C9A	126.93 (15)	C13—C14—H14A	111.1 (9)
C7—C8—C9B	110.7 (6)	C13—C14—H14B	111.1 (10)
C7—C8—H8	117.8 (10)	H14A—C14—H14B	107.7 (14)
C9A—C8—H8	115.3 (10)	C13—C14—H14C	108.0 (10)
C9B—C8—H8	109.2 (11)	H14A—C14—H14C	109.8 (14)
C8—C9A—C10A	111.28 (16)	H14B—C14—H14C	109.1 (14)
C8—C9A—H9A	110.1 (12)	C1—N1—N2	117.11 (11)
C10A—C9A—H9A	108.3 (13)	C12—N2—N1	117.59 (11)
C8—C9A—H9B	109.3 (11)	C12—N2—H2	118.7 (11)
C10A—C9A—H9B	112.1 (11)	N1—N2—H2	122.9 (11)
H9A—C9A—H9B	105.6 (16)	C12—N3—C13	123.81 (11)
C9A—C10A—H10A	109.6 (13)	C12—N3—H3	116.1 (11)
C9A—C10A—H10B	109.5 (16)	C13—N3—H3	120.0 (11)
H10A—C10A—H10B	111 (2)

N1—C1—C2—C3	−177.86 (13)	C1—C5—C6—C7	79.84 (15)
C5—C1—C2—C3	4.82 (14)	C5—C6—C7—C8	−138.74 (16)
C1—C2—C3—C4	−5.70 (13)	C6—C7—C8—C9A	4.5 (3)
C2—C3—C4—C5	5.04 (15)	C6—C7—C8—C9B	−50.1 (6)
C2—C3—C4—C11	−174.65 (12)	C7—C8—C9A—C10A	−106.5 (2)
C11—C4—C5—C1	177.60 (13)	C7—C8—C9B—C10B	132.7 (10)
C3—C4—C5—C1	−2.06 (15)	C5—C1—N1—N2	177.52 (10)
C11—C4—C5—C6	−1.1 (2)	C2—C1—N1—N2	0.47 (19)
C3—C4—C5—C6	179.29 (12)	N3—C12—N2—N1	−4.03 (17)
N1—C1—C5—C4	−179.51 (11)	S1—C12—N2—N1	176.25 (9)
C2—C1—C5—C4	−1.91 (14)	C1—N1—N2—C12	−172.87 (11)
N1—C1—C5—C6	−0.76 (18)	N2—C12—N3—C13	−178.66 (11)
C2—C1—C5—C6	176.84 (11)	S1—C12—N3—C13	1.04 (18)
C4—C5—C6—C7	−101.67 (16)	C14—C13—N3—C12	−179.07 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1ⁱ	0.873 (18)	2.608 (18)	3.4808 (12)	177.6 (15)
N3—H3···N1	0.828 (16)	2.187 (15)	2.6008 (15)	111.0 (13)
C2—H2A···S1ⁱ	1.003 (16)	2.822 (15)	3.3535 (13)	113.7 (10)
C13—H13B···N1ⁱⁱ	0.966 (15)	2.655 (15)	3.5466 (17)	153.5 (12)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

We gratefully acknowledge financial support by the State of North Rhine-Westphalia, Germany. ABO is a former DAAD scholarship holder and alumnus of the University of Bonn, Germany, and thanks both of the institutions for the long-time support.

Funding information

Funding for this research was provided by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brazil (CAPES) - Finance Code 001.

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