The asymmetric unit of the title molecule contains a planar oxadiazole, a thiophene and two phenyl rings. In the crystal, π–π stacking interactions and C—H⋯π(ring) interactions help to consolidate the packing.
Keywords: 4-oxadiazol, 4-chlorophenyl, crystal structure
Abstract
The title thiophene-chalcone derivative, C22H17ClN2O2S2, contains a planar oxadiazole, a thiophene and two phenyl rings. The dihedral angle between the oxadiazole and thiophene rings is 27.45 (10)°, and they are oriented with respect to the chlorophenyl and methylphenyl rings at 22.61 (10), 67.07 (8) and 49.16 (10), 87.22 (8)°, respectively, while the phenyl rings are oriented at 51.78 (9)°. In the crystal, π–π stacking interactions and C—H⋯π(ring) interactions help to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (31.6%), H⋯C/C⋯H (20.0%), H⋯S/S⋯H (14.2%) and H⋯O/O⋯H (9.5%) interactions.
1. Chemical context
Oxadiazole is an important structural motif in medicinal chemistry for its role as a pharmacophore and a ligand-binding scaffold (Boström et al., 2012 ▸). Among its four isomeric forms, the 1,3,4-oxadiazole ring has attracted considerable attention owing to its broad spectrum of biological activities (Salahuddin et al., 2017 ▸; Patel et al., 2014 ▸). Numerous 1,3,4- and 1,2,4-oxadiazole derivatives have been reported to exhibit antibacterial, anti-inflammatory, antitubercular, anti-HIV, antifungal, cathepsin K inhibitory, monoamine oxidase inhibitory, antidiabetic, tyrosinase inhibitory, antioxidant and anticancer activities (Palaska et al., 2002 ▸; Kadi et al., 2007 ▸; Alisi et al., 2020 ▸).
In recent years, thiophene-containing chalcone derivatives have emerged as an important class of compounds because of their extended π-conjugated systems and promising applications in medicinal and materials chemistry (Shalaby et al., 2023 ▸). Adding heterocyclic moieties to the chalcone scaffold is a well-established approach for modulating molecular geometry and physicochemical properties. In this context, the integration of a 1,3,4-oxadiazole ring with a thiophene-chalcone framework generates conjugated molecular systems of significant structural and potential biological interest. As part of our ongoing research on heterocyclic compounds, the title thiophene-chalcone derivative containing a 1,3,4-oxadiazole unit was synthesized and its crystal structure was elucidated to investigate its molecular conformation and intermolecular interactions governing the crystal packing. Herein, we report the molecular and crystal structures together with a Hirshfeld surface (HS) analysis of the title compound.
2. Structural commentary
The title thiophene-chalcone derivative contains a planar oxadiazole, a thiophene and two phenyl rings (Fig. 1 ▸). The phenyl [A (C1–C6) and D (C16–C21)], oxadiazole [B (O1/N1/N2/C7/C8)], and thiophene [C (S2/C12–C15)] rings are oriented at dihedral angles of A/B = 22.61 (10)°, A/C = 49.16 (10)°, A/D = 51.78 (9)°, B/C = 27.45 (10)°, B/D = 67.07 (8)° and C/D = 87.22 (8)°. The chlorine atom Cl1 is displaced by −0.0389 (11) Å from the plane of the phenyl ring A. Atoms C22 and C9 are only −0.003 (4) Å and −0.002 (3) Å away from phenyl ring D. Atoms S1 and C9 are −0.0433 (9) Å and 0.002 (3) Å distant from the oxadiazole, B, ring plane, while atom C11 resides 0.016 (3) Å above the thiophene, C, ring plane. The specified atoms are, hence, essentially coplanar with the planes of the rings they are attached to. The bond lengths (Allen et al., 1987 ▸) and angles are all within normal ranges.
Figure 1.
The asymmetric unit with atom-numbering scheme and 50% probability ellipsoids.
3. Supramolecular features
In the crystal, the thiophene-to-thiophene contacts form pairs, which are arranged along the c-axis direction, and adjacent pairs are also essentially arranged in front and behind in the a-axis direction, albeit slightly displaced with regard to the b-axis direction. The chlorophenyl-to-chlorophenyl contacts also form pairs with contacts arranged along the a-axis direction. However, none of these pairs has further contacts that would extend into columns, ribbons or layers (Fig. 2 ▸). The π–π stacking interactions involve parallel chlorophenyl rings A and approximately parallel thiophene rings C. The centroid-to-centroid distances are 3.6612 (18) Å [dihedral angle = 0.00 (16)° slippage = 1.466 Å] and 3.844 (3) Å [dihedral angle = 2.0 (2)°; slippage = 0.871 Å], respectively. Together with the two C—H⋯π(ring) interactions (Table 1 ▸), these contacts help consolidate the overall packing.
Figure 2.
A partial packing diagram viewed down the b–axis direction.
Table 1. Hydrogen-bond geometry (Å, °).
Cg3 and Cg4 are the centroids of the C1–C6 and C16–C21 rings.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C20—H20⋯Cg3i | 0.93 | 2.83 | 3.726 (3) | 164 |
| C22—H22B⋯Cg4ii | 0.96 | 2.92 | 3.671 (4) | 136 |
Symmetry codes: (i) 
; (ii) 
.
The intermolecular interactions in the crystal were further visualized through a Hirshfeld surface (HS) analysis using CrystalExplorer 17.5 (Spackman et al., 2021 ▸). Fig. 3 ▸ shows the Hirshfeld surface for the title molecule plotted over dnorm. The white surface indicates contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter and longer than the van der Waals radii, respectively. The π–π stackings and the two C—H⋯π(ring) interactions are indicated in Fig. 4 ▸a,b by the presence of adjacent red and blue triangles, and Fig. 4 ▸c,d by the presence of red π-holes, respectively.
Figure 3.
View of the three-dimensional Hirshfeld surface for the title molecule plotted over dnorm in the range from −0.2794 to 1.6393 a.u.
Figure 4.
Four orientations of the shape-index showing (a) and (b) the π–π and (c) and (d) the C—H⋯π(ring) interactions.
The overall two-dimensional fingerprint plot is shown in Fig. 5 ▸a and those delineated into H⋯H, H⋯C/C⋯H, H⋯S/S⋯H, H⋯O/O⋯H, H⋯Cl/Cl⋯H, C⋯C, C⋯Cl/Cl⋯C, C⋯S/S⋯C, O⋯S/S⋯O, H⋯N/N⋯H, Cl⋯Cl, O⋯Cl/Cl⋯O, N⋯Cl/Cl⋯N, N⋯S/S⋯N, C⋯O/O⋯C, O⋯O, N⋯O/O⋯N and C⋯N/N⋯C interactions are illustrated in Fig. 5 ▸(b)–(t), respectively. According to the two-dimensional fingerprint plots the H⋯H, H⋯C/C⋯ H, H⋯S/S⋯H and H⋯O/O⋯H contacts make the most significant contributions to the Hirshfeld surface, at 31.6%, 20.0%, 14.2% and 9.5%, respectively (Fig. 5 ▸).
Figure 5.
The full two-dimensional fingerprint plots for the title molecule, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯ S/S⋯H, (e) H⋯O/O⋯H, (f) H⋯Cl/Cl⋯H, (g) C⋯C, (h) C⋯Cl/Cl⋯C, (i) C⋯S/S⋯C, (j) O⋯S/S⋯O, (k) H⋯N/N⋯H, (l) Cl⋯Cl, (m) O⋯Cl/Cl⋯O, (n) N⋯Cl/Cl⋯N, (o) N⋯S/S⋯N, (p) C⋯O/O⋯C, (r) O⋯O, (s) N⋯O/O⋯N and (t) C⋯N/N⋯ C interactions. The di and de values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 6.01, updated February 2026; Groom et al., 2016 ▸) revealed that the crystal structure of the title compound has not been reported previously. However, with the exclusion of metal containing structures, ten structurally related compounds containing both thiophene and 1,3,4-oxadiazole-2(3H)-thione moieties were identified. These are N-[2-(2-thienyl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)vinyl]benzamide (CSD refcode ENOPEE; Sharma et al., 2016 ▸), 5-(2-thienyl)-1,3,4-oxadiazole-2(3H)-thione (FUSDII; Burcu Arslan et al., 2014 ▸), N-[1-(5-sulfanylidene-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-(2-thienyl)vinyl]acetamide (HAJHAF; Karanth et al., 2019 ▸), 4-methyl-N-[1-(5-sulfanylidene-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2-(thiophen-2-yl)ethenyl]benzamide (HAJHOT; Karanth et al., 2019 ▸), 3-[(4-phenylpiperazin-1-yl)methyl]-5-(2-thienyl)-1,3,4-oxadiazole-2(3H)-thione (IDOBUA; El-Emam et al., 2013 ▸), 3-[(4-phenylpiperidin-1-yl)methyl]-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione (MURSAX; Al-Wahaibi et al., 2025 ▸), 3-{[4-(4-fluorophenyl)piperazin-1-yl]methyl}-5-(2-thienyl)-1,3,4-oxadiazole-2(3H)-thione (MUXBAK; Al-Omary et al., 2015a ▸), 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(2-thienyl)-1,3,4-oxadiazole-2(3H)-thione (NUZJUP; Al-Alshaikh et al., 2016 ▸), 3-[(4-benzylpiperazin-1-yl)methyl]-5-(2-thienyl)-1,3,4-oxadiazole-2(3H)-thione (VUBYUO; Al-Omary et al., 2015b ▸), and 3-{[methyl(phenyl)amino]methyl}-5-(2-thienyl)-1,3,4-oxadiazole-2(3H)-thione (ZAPJIL; El-Emam et al., 2012 ▸). Notably, in only three of these structures are the thiophene and oxadiazole moieties not directly linked to each other (ENOPEE, HAJHAF, HAJHOT). Two of these molecules have only the two planar ring systems which comprised the search criteria (FUSDII and HAJHAF), the other eight all have a single additional phenyl ring while none consists of four planar ring systems as the title compound does.
Further thiophene-bearing molecules with structural features resembling those of the title compound include (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (AFAXUC; Chantrapromma et al., 2013 ▸), 1-(4-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (ROTNUN; da Silva et al., 2024 ▸), 1-[3-(4-methoxy- phenyl)sydnon-4-yl]-3-(thiophen-2-yl)prop-2-en-1-one (EVAWIH; Shih, 2004 ▸), (E)-1-(1H-pyrrol-2-yl)-3-(thiophen-2-yl) prop-2-en-1-one (RUFLEM; Sweeting et al., 2020 ▸), (2E)-1-(4-bromophenyl)-3-(thiophen-2-yl)prop-2-en-1-one (GENXED01; Arshad et al., 2017 ▸) and 1-(4-methoxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one (ZOVPOS; Pugh et al., 2019 ▸). In addition, compounds incorporating related 1,3,4-oxadiazole frameworks were also found, including 4-hydroxy-3-{[5-(pyridin-3-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}pent-3-en-2-one (CARJIS; Zhang et al., 2021 ▸), 5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-ylmethanone (DIPGUI; Bhukta et al., 2023 ▸) and 1-(4-chlorophenyl)-2-{[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}ethan-1-one (GAVMOI; Kumar et al., 2017 ▸).
5. Synthesis and crystallization
Methyl 4-chlorobenzoate (15 ml, 0.10 mol) was refluxed with hydrazine hydrate (6 ml, 0.12 mol) in ethanol (10 ml) for 4 h. The reaction mixture was cooled and poured into ice-cold water. The resulting solid was filtered, washed with water and dried to afford 4-chlorobenzohydrazide (91%, m.p. 428 K). 4-Chlorobenzohydrazide (3.41 g, 0.02 mol) was then treated with KOH (0.02 mol) and carbon disulfide (0.04 mol) in ethanol under reflux for 4 h. The reaction mixture was cooled, acidified with dilute HCl, and the precipitated solid was filtered, washed with water, and recrystallized from ethanol to furnish 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-thiol (83%, m.p. 503 K). Subsequently, 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-thiol was refluxed with the (2Z)-3-(4-methylphenyl)-1-(thiophen-2-yl)prop-2-en-1-one in ethanol for 4 h. After completion of the reaction, the mixture was cooled and poured into ice-cold water. The precipitated product was filtered, washed thoroughly with water, dried, and recrystallized from ethanol to afford 3-[5-(4-chlorophenyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl) propan-1-one as a pure solid in 80% yield (m.p. 433 K). IR (KBr) cm−1: 1645 (C=O str.), 1594 (C=N str.), 1214 (C=S str.) and 3069 (Ar. C—H str.).
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The C-bound hydrogen-atom positions were calculated geometrically at distances of 0.93 Å (for aromatic CH), 0.98 Å (for methine CH), 0.97 Å (for methylene CH) and 0.96 Å (for methyl CH) and refined using a riding model by applying the constraint of Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H atoms and k = 1.2 for the other H atoms. Four reflections, 0 2 0, −2 0 2, 0 0 2 and −1 1 2, were omitted, the first three being affected by the beam stop and the fourth being a clear outlier.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C22H17ClN2O2S2 |
| M r | 440.94 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 300 |
| a, b, c (Å) | 20.7798 (3), 13.1963 (4), 16.1047 (4) |
| β (°) | 102.440 (3) |
| V (Å3) | 4312.49 (19) |
| Z | 8 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.39 |
| Crystal size (mm) | 0.35 × 0.25 × 0.18 |
| Data collection | |
| Diffractometer | Bruker D8 Venture Diffractometer |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 53818, 3823, 2660 |
| R int | 0.117 |
| (sin θ/λ)max (Å−1) | 0.597 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.133, 1.06 |
| No. of reflections | 3823 |
| No. of parameters | 263 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.21, −0.34 |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989026008819/yz2084sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026008819/yz2084Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989026008819/yz2084Isup3.cml
CCDC reference: 2583252
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Yenepoya Deemed to be University for the facilities and financial support. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004). The authors’ contributions are as follows. Conceptualization, SJ, SK and TH; synthesis, SJ; X-ray analysis, SJ, SK and TH; Hirshfeld surface analysis, TH; writing (review and editing of the manuscript), SJ, SK and TH; supervision, TH and SK.
supplementary crystallographic information
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Crystal data
| C22H17ClN2O2S2 | F(000) = 1824 |
| Mr = 440.94 | Dx = 1.358 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 20.7798 (3) Å | Cell parameters from 9893 reflections |
| b = 13.1963 (4) Å | θ = 2.9–24.4° |
| c = 16.1047 (4) Å | µ = 0.39 mm−1 |
| β = 102.440 (3)° | T = 300 K |
| V = 4312.49 (19) Å3 | Block, colourless |
| Z = 8 | 0.35 × 0.25 × 0.18 mm |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Data collection
| Bruker D8 Venture Diffractometer | Rint = 0.117 |
| φ and ω scans | θmax = 25.1°, θmin = 3.4° |
| 53818 measured reflections | h = −24→24 |
| 3823 independent reflections | k = −15→15 |
| 2660 reflections with I > 2σ(I) | l = −19→19 |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
| wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0485P)2 + 5.5114P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 3823 reflections | Δρmax = 0.21 e Å−3 |
| 263 parameters | Δρmin = −0.34 e Å−3 |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Special details
| 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. |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | −0.02304 (5) | 0.68488 (8) | 0.36140 (7) | 0.0940 (4) | |
| S1 | 0.21099 (4) | 0.09611 (6) | 0.55083 (6) | 0.0646 (3) | |
| S2 | 0.51040 (4) | 0.33068 (8) | 0.88521 (6) | 0.0716 (3) | |
| O1 | 0.15497 (9) | 0.27611 (14) | 0.50923 (12) | 0.0492 (5) | |
| O2 | 0.40086 (11) | 0.20490 (18) | 0.79037 (17) | 0.0766 (7) | |
| N1 | 0.19842 (11) | 0.37647 (17) | 0.61720 (14) | 0.0444 (6) | |
| N2 | 0.22459 (11) | 0.27964 (17) | 0.62889 (14) | 0.0433 (6) | |
| C1 | 0.03143 (15) | 0.5946 (3) | 0.4151 (2) | 0.0606 (9) | |
| C2 | 0.04901 (17) | 0.5143 (3) | 0.3706 (2) | 0.0698 (10) | |
| H2 | 0.032596 | 0.509239 | 0.312306 | 0.084* | |
| C3 | 0.09082 (16) | 0.4415 (3) | 0.41243 (19) | 0.0586 (8) | |
| H3 | 0.102859 | 0.386888 | 0.382601 | 0.070* | |
| C4 | 0.11520 (13) | 0.4497 (2) | 0.49971 (18) | 0.0459 (7) | |
| C5 | 0.09805 (14) | 0.5322 (2) | 0.54302 (19) | 0.0497 (7) | |
| H5 | 0.115268 | 0.538910 | 0.601040 | 0.060* | |
| C6 | 0.05581 (15) | 0.6043 (2) | 0.5010 (2) | 0.0548 (8) | |
| H6 | 0.043768 | 0.659303 | 0.530460 | 0.066* | |
| C7 | 0.15780 (13) | 0.3708 (2) | 0.54492 (17) | 0.0435 (7) | |
| C8 | 0.19816 (14) | 0.2172 (2) | 0.56537 (18) | 0.0460 (7) | |
| C9 | 0.27418 (13) | 0.2523 (2) | 0.70549 (17) | 0.0437 (7) | |
| H9 | 0.294754 | 0.188761 | 0.693418 | 0.052* | |
| C10 | 0.32768 (14) | 0.3332 (2) | 0.72144 (19) | 0.0506 (7) | |
| H10A | 0.337773 | 0.353284 | 0.667709 | 0.061* | |
| H10B | 0.311617 | 0.392485 | 0.746326 | 0.061* | |
| C11 | 0.38986 (14) | 0.2951 (2) | 0.78047 (19) | 0.0508 (7) | |
| C12 | 0.43695 (14) | 0.3706 (2) | 0.82279 (19) | 0.0526 (8) | |
| C13 | 0.43258 (19) | 0.4740 (3) | 0.8214 (3) | 0.0882 (13) | |
| H13 | 0.396509 | 0.510482 | 0.791966 | 0.106* | |
| C14 | 0.4906 (3) | 0.5181 (4) | 0.8709 (4) | 0.126 (2) | |
| H14 | 0.497143 | 0.587718 | 0.877001 | 0.151* | |
| C15 | 0.5353 (2) | 0.4492 (3) | 0.9083 (3) | 0.0953 (14) | |
| H15 | 0.575662 | 0.465943 | 0.943140 | 0.114* | |
| C16 | 0.24206 (13) | 0.2332 (2) | 0.77969 (17) | 0.0424 (6) | |
| C17 | 0.24210 (15) | 0.1367 (2) | 0.81390 (19) | 0.0488 (7) | |
| H17 | 0.262005 | 0.083791 | 0.790687 | 0.059* | |
| C18 | 0.21309 (15) | 0.1179 (2) | 0.8818 (2) | 0.0542 (8) | |
| H18 | 0.213774 | 0.052413 | 0.903324 | 0.065* | |
| C19 | 0.18314 (14) | 0.1939 (2) | 0.91841 (19) | 0.0498 (7) | |
| C20 | 0.18410 (17) | 0.2903 (2) | 0.8847 (2) | 0.0639 (9) | |
| H20 | 0.164964 | 0.343337 | 0.908721 | 0.077* | |
| C21 | 0.21262 (17) | 0.3099 (2) | 0.8164 (2) | 0.0597 (8) | |
| H21 | 0.211976 | 0.375448 | 0.795043 | 0.072* | |
| C22 | 0.15170 (17) | 0.1746 (3) | 0.9930 (2) | 0.0653 (9) | |
| H22A | 0.104615 | 0.174914 | 0.974141 | 0.098* | |
| H22B | 0.164729 | 0.226663 | 1.034900 | 0.098* | |
| H22C | 0.165739 | 0.109833 | 1.017591 | 0.098* |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0765 (7) | 0.0946 (7) | 0.1055 (8) | 0.0220 (6) | 0.0074 (6) | 0.0429 (6) |
| S1 | 0.0683 (6) | 0.0478 (5) | 0.0757 (6) | −0.0032 (4) | 0.0109 (5) | −0.0161 (4) |
| S2 | 0.0460 (5) | 0.0927 (7) | 0.0693 (6) | −0.0034 (4) | −0.0026 (4) | 0.0089 (5) |
| O1 | 0.0486 (12) | 0.0504 (12) | 0.0448 (11) | −0.0060 (9) | 0.0013 (9) | −0.0091 (9) |
| O2 | 0.0548 (14) | 0.0589 (15) | 0.105 (2) | 0.0017 (11) | −0.0062 (13) | 0.0120 (14) |
| N1 | 0.0457 (13) | 0.0436 (13) | 0.0407 (13) | −0.0005 (11) | 0.0023 (11) | −0.0026 (10) |
| N2 | 0.0441 (13) | 0.0417 (13) | 0.0417 (13) | −0.0007 (10) | 0.0044 (11) | −0.0039 (10) |
| C1 | 0.0454 (18) | 0.063 (2) | 0.071 (2) | 0.0015 (15) | 0.0070 (16) | 0.0187 (18) |
| C2 | 0.066 (2) | 0.088 (3) | 0.0461 (19) | 0.006 (2) | −0.0075 (17) | 0.0044 (18) |
| C3 | 0.058 (2) | 0.070 (2) | 0.0438 (18) | 0.0051 (16) | 0.0020 (15) | −0.0057 (15) |
| C4 | 0.0380 (16) | 0.0526 (17) | 0.0444 (17) | −0.0045 (13) | 0.0032 (13) | −0.0002 (13) |
| C5 | 0.0446 (17) | 0.0534 (18) | 0.0477 (17) | −0.0074 (14) | 0.0022 (14) | −0.0024 (14) |
| C6 | 0.0496 (18) | 0.0501 (18) | 0.066 (2) | −0.0033 (14) | 0.0149 (16) | 0.0018 (16) |
| C7 | 0.0385 (15) | 0.0487 (16) | 0.0418 (16) | −0.0037 (13) | 0.0057 (13) | −0.0057 (13) |
| C8 | 0.0398 (16) | 0.0513 (17) | 0.0473 (17) | −0.0056 (13) | 0.0102 (13) | −0.0028 (14) |
| C9 | 0.0413 (16) | 0.0424 (15) | 0.0451 (16) | 0.0017 (12) | 0.0040 (13) | 0.0005 (13) |
| C10 | 0.0411 (16) | 0.0544 (17) | 0.0534 (18) | −0.0026 (13) | 0.0036 (14) | 0.0057 (14) |
| C11 | 0.0439 (17) | 0.0567 (19) | 0.0519 (18) | 0.0007 (14) | 0.0102 (14) | 0.0055 (15) |
| C12 | 0.0431 (17) | 0.064 (2) | 0.0477 (17) | −0.0010 (14) | 0.0028 (14) | −0.0016 (15) |
| C13 | 0.074 (3) | 0.064 (2) | 0.107 (3) | −0.0009 (19) | −0.025 (2) | −0.016 (2) |
| C14 | 0.102 (4) | 0.076 (3) | 0.167 (5) | −0.008 (3) | −0.040 (3) | −0.038 (3) |
| C15 | 0.064 (3) | 0.106 (3) | 0.099 (3) | −0.012 (2) | −0.017 (2) | −0.017 (3) |
| C16 | 0.0370 (15) | 0.0421 (15) | 0.0457 (16) | 0.0013 (12) | 0.0036 (12) | −0.0011 (13) |
| C17 | 0.0560 (18) | 0.0391 (15) | 0.0517 (18) | 0.0030 (13) | 0.0122 (15) | −0.0035 (13) |
| C18 | 0.064 (2) | 0.0408 (16) | 0.0592 (19) | −0.0011 (14) | 0.0158 (16) | 0.0079 (14) |
| C19 | 0.0435 (16) | 0.0520 (17) | 0.0546 (18) | 0.0028 (14) | 0.0121 (14) | 0.0045 (14) |
| C20 | 0.071 (2) | 0.0532 (19) | 0.075 (2) | 0.0200 (16) | 0.0325 (19) | 0.0060 (17) |
| C21 | 0.072 (2) | 0.0445 (17) | 0.068 (2) | 0.0130 (16) | 0.0276 (18) | 0.0105 (16) |
| C22 | 0.066 (2) | 0.067 (2) | 0.069 (2) | 0.0035 (17) | 0.0272 (18) | 0.0094 (17) |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Geometric parameters (Å, º)
| Cl1—C1 | 1.740 (3) | C10—C11 | 1.516 (4) |
| S1—C8 | 1.644 (3) | C10—H10A | 0.9700 |
| S2—C15 | 1.664 (4) | C10—H10B | 0.9700 |
| S2—C12 | 1.719 (3) | C11—C12 | 1.458 (4) |
| O1—C8 | 1.371 (3) | C12—C13 | 1.368 (5) |
| O1—C7 | 1.371 (3) | C13—C14 | 1.420 (5) |
| O2—C11 | 1.216 (3) | C13—H13 | 0.9300 |
| N1—C7 | 1.284 (3) | C14—C15 | 1.345 (6) |
| N1—N2 | 1.386 (3) | C14—H14 | 0.9300 |
| N2—C8 | 1.336 (3) | C15—H15 | 0.9300 |
| N2—C9 | 1.472 (3) | C16—C21 | 1.381 (4) |
| C1—C2 | 1.373 (5) | C16—C17 | 1.387 (4) |
| C1—C6 | 1.373 (5) | C17—C18 | 1.380 (4) |
| C2—C3 | 1.370 (4) | C17—H17 | 0.9300 |
| C2—H2 | 0.9300 | C18—C19 | 1.378 (4) |
| C3—C4 | 1.392 (4) | C18—H18 | 0.9300 |
| C3—H3 | 0.9300 | C19—C20 | 1.384 (4) |
| C4—C5 | 1.381 (4) | C19—C22 | 1.508 (4) |
| C4—C7 | 1.457 (4) | C20—C21 | 1.381 (4) |
| C5—C6 | 1.370 (4) | C20—H20 | 0.9300 |
| C5—H5 | 0.9300 | C21—H21 | 0.9300 |
| C6—H6 | 0.9300 | C22—H22A | 0.9600 |
| C9—C16 | 1.510 (4) | C22—H22B | 0.9600 |
| C9—C10 | 1.523 (4) | C22—H22C | 0.9600 |
| C9—H9 | 0.9800 | ||
| C15—S2—C12 | 92.10 (19) | H10A—C10—H10B | 108.0 |
| C8—O1—C7 | 106.1 (2) | O2—C11—C12 | 121.3 (3) |
| C7—N1—N2 | 103.4 (2) | O2—C11—C10 | 121.2 (3) |
| C8—N2—N1 | 112.4 (2) | C12—C11—C10 | 117.5 (3) |
| C8—N2—C9 | 126.1 (2) | C13—C12—C11 | 129.7 (3) |
| N1—N2—C9 | 121.5 (2) | C13—C12—S2 | 111.3 (2) |
| C2—C1—C6 | 121.1 (3) | C11—C12—S2 | 119.1 (2) |
| C2—C1—Cl1 | 119.1 (3) | C12—C13—C14 | 110.8 (4) |
| C6—C1—Cl1 | 119.8 (3) | C12—C13—H13 | 124.6 |
| C3—C2—C1 | 119.8 (3) | C14—C13—H13 | 124.6 |
| C3—C2—H2 | 120.1 | C15—C14—C13 | 113.2 (4) |
| C1—C2—H2 | 120.1 | C15—C14—H14 | 123.4 |
| C2—C3—C4 | 119.7 (3) | C13—C14—H14 | 123.4 |
| C2—C3—H3 | 120.1 | C14—C15—S2 | 112.6 (3) |
| C4—C3—H3 | 120.1 | C14—C15—H15 | 123.7 |
| C5—C4—C3 | 119.6 (3) | S2—C15—H15 | 123.7 |
| C5—C4—C7 | 120.4 (3) | C21—C16—C17 | 117.7 (3) |
| C3—C4—C7 | 119.9 (3) | C21—C16—C9 | 121.9 (3) |
| C6—C5—C4 | 120.4 (3) | C17—C16—C9 | 120.4 (2) |
| C6—C5—H5 | 119.8 | C18—C17—C16 | 121.1 (3) |
| C4—C5—H5 | 119.8 | C18—C17—H17 | 119.4 |
| C5—C6—C1 | 119.4 (3) | C16—C17—H17 | 119.4 |
| C5—C6—H6 | 120.3 | C19—C18—C17 | 121.5 (3) |
| C1—C6—H6 | 120.3 | C19—C18—H18 | 119.2 |
| N1—C7—O1 | 113.2 (2) | C17—C18—H18 | 119.2 |
| N1—C7—C4 | 128.4 (3) | C18—C19—C20 | 117.0 (3) |
| O1—C7—C4 | 118.4 (2) | C18—C19—C22 | 122.1 (3) |
| N2—C8—O1 | 104.9 (2) | C20—C19—C22 | 120.9 (3) |
| N2—C8—S1 | 131.0 (2) | C21—C20—C19 | 122.0 (3) |
| O1—C8—S1 | 124.1 (2) | C21—C20—H20 | 119.0 |
| N2—C9—C16 | 110.8 (2) | C19—C20—H20 | 119.0 |
| N2—C9—C10 | 108.9 (2) | C16—C21—C20 | 120.6 (3) |
| C16—C9—C10 | 114.5 (2) | C16—C21—H21 | 119.7 |
| N2—C9—H9 | 107.4 | C20—C21—H21 | 119.7 |
| C16—C9—H9 | 107.4 | C19—C22—H22A | 109.5 |
| C10—C9—H9 | 107.4 | C19—C22—H22B | 109.5 |
| C11—C10—C9 | 111.5 (2) | H22A—C22—H22B | 109.5 |
| C11—C10—H10A | 109.3 | C19—C22—H22C | 109.5 |
| C9—C10—H10A | 109.3 | H22A—C22—H22C | 109.5 |
| C11—C10—H10B | 109.3 | H22B—C22—H22C | 109.5 |
| C9—C10—H10B | 109.3 | ||
| C7—N1—N2—C8 | −1.9 (3) | N2—C9—C10—C11 | −161.9 (2) |
| C7—N1—N2—C9 | −179.9 (2) | C16—C9—C10—C11 | 73.4 (3) |
| C6—C1—C2—C3 | 0.9 (5) | C9—C10—C11—O2 | 20.9 (4) |
| Cl1—C1—C2—C3 | −178.7 (3) | C9—C10—C11—C12 | −161.0 (3) |
| C1—C2—C3—C4 | −0.1 (5) | O2—C11—C12—C13 | −178.0 (4) |
| C2—C3—C4—C5 | −1.3 (5) | C10—C11—C12—C13 | 3.9 (5) |
| C2—C3—C4—C7 | 177.8 (3) | O2—C11—C12—S2 | 2.0 (4) |
| C3—C4—C5—C6 | 1.8 (4) | C10—C11—C12—S2 | −176.1 (2) |
| C7—C4—C5—C6 | −177.3 (3) | C15—S2—C12—C13 | −0.6 (3) |
| C4—C5—C6—C1 | −1.0 (4) | C15—S2—C12—C11 | 179.4 (3) |
| C2—C1—C6—C5 | −0.4 (5) | C11—C12—C13—C14 | −179.1 (4) |
| Cl1—C1—C6—C5 | 179.2 (2) | S2—C12—C13—C14 | 0.9 (5) |
| N2—N1—C7—O1 | 1.0 (3) | C12—C13—C14—C15 | −1.0 (7) |
| N2—N1—C7—C4 | 179.4 (3) | C13—C14—C15—S2 | 0.6 (7) |
| C8—O1—C7—N1 | 0.2 (3) | C12—S2—C15—C14 | 0.0 (4) |
| C8—O1—C7—C4 | −178.5 (2) | N2—C9—C16—C21 | −67.6 (3) |
| C5—C4—C7—N1 | −21.6 (5) | C10—C9—C16—C21 | 56.1 (4) |
| C3—C4—C7—N1 | 159.2 (3) | N2—C9—C16—C17 | 113.2 (3) |
| C5—C4—C7—O1 | 156.8 (3) | C10—C9—C16—C17 | −123.1 (3) |
| C3—C4—C7—O1 | −22.4 (4) | C21—C16—C17—C18 | 0.6 (4) |
| N1—N2—C8—O1 | 2.0 (3) | C9—C16—C17—C18 | 179.9 (3) |
| C9—N2—C8—O1 | 179.9 (2) | C16—C17—C18—C19 | −0.2 (5) |
| N1—N2—C8—S1 | −178.3 (2) | C17—C18—C19—C20 | −0.7 (5) |
| C9—N2—C8—S1 | −0.4 (4) | C17—C18—C19—C22 | −179.5 (3) |
| C7—O1—C8—N2 | −1.3 (3) | C18—C19—C20—C21 | 1.1 (5) |
| C7—O1—C8—S1 | 179.0 (2) | C22—C19—C20—C21 | 180.0 (3) |
| C8—N2—C9—C16 | −98.7 (3) | C17—C16—C21—C20 | −0.3 (5) |
| N1—N2—C9—C16 | 79.0 (3) | C9—C16—C21—C20 | −179.5 (3) |
| C8—N2—C9—C10 | 134.5 (3) | C19—C20—C21—C16 | −0.7 (5) |
| N1—N2—C9—C10 | −47.8 (3) |
3-[5-(4-Chlorophenyl)-2-sulfanylidene-1,3,4-oxadiazol-3-yl]-3-(4-methylphenyl)-1-(thiophen-2-yl)propan-1-one. Hydrogen-bond geometry (Å, º)
Cg3 and Cg4 are the centroids of the C1–C6 and C16–C21 rings.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C20—H20···Cg3i | 0.93 | 2.83 | 3.726 (3) | 164 |
| C22—H22B···Cg4ii | 0.96 | 2.92 | 3.671 (4) | 136 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1/2, −y+1/2, −z+2.
References
- Al-Alshaikh, M. A., Abuelizz, H. A., El-Emam, A. A., Abdelbaky, M. S. M. & Garcia-Granda, S. (2016). Acta Cryst. E72, 269–272. [DOI] [PMC free article] [PubMed]
- Alisi, I. O., Uzairu, A. & Abechi, S. E. (2020). Heliyon6, e03683. [DOI] [PMC free article] [PubMed]
- Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 216, S1–S19.
- Al-Omary, F. A. M., AlRabiah, H., Ghabbour, H. A., Quah, C. K., Fun, H.-K. & El-Emam, A. A. (2015a). Z. Krist.-New Cryst. Struct.230, 267–268.
- Al-Omary, F. A. M., El-Emam, A. A., Ghabbour, H. A., Chidan Kumar, C. S., Quah, C. K. & Fun, H.-K. (2015b). Acta Cryst. E71, o175–o176. [DOI] [PMC free article] [PubMed]
- Al-Wahaibi, L. H., Blacque, O., Tiekink, E. R. T. & El-Emam, A. A. (2025). Z. Krist. New Cryst. Struct.240, 491–493.
- Arshad, M. N., Al-Dies, A. M., Asiri, A. M., Khalid, M., Birinji, A. S., Al-Amry, K. A. & Braga, A. A. (2017). J. Mol. Struct.1141, 142–156.
- Bhukta, S., Chatterjee, R., Angajala, K. K. & Dandela, R. (2023). Tetrahedron Lett.128, 154714.
- Boström, J., Hogner, A., Llinàs, A., Wellner, E. & Plowright, A. T. (2012). J. Med. Chem.55, 1817–1830. [DOI] [PubMed]
- Bruker (2021). APEX4, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
- Burcu Arslan, N., Özdemir, N., Dayan, O., Dege, N., Koparır, M., Koparır, P. & Muğlu, H. (2014). Chem. Phys.439, 1–11.
- Chantrapromma, S., Ruanwas, P., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o1004–o1005. [DOI] [PMC free article] [PubMed]
- da Silva, P. T., da Silva Mendes, F. R., Almeida-Neto, F. W. Q., Marinho, E. S., da Silva, L., da Silva Julião, M. S., Marinho, M. M., Vidal, L. M. T., Ayala, A. P., Coutinho, H. D. M., Rocha, J. E., Gomes, A. O. C. V., Lucio, F. N. M., Guedes, J. M., Teixeira, A. M. R. & Silva dos Santos, H. (2024). J. Mol. Struct.1312, 138497.
- El-Emam, A. A., Al-Omar, M. A., Al-Obaid, A.-R. M., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o684. [DOI] [PMC free article] [PubMed]
- El-Emam, A. A., Al-Omar, M. A., Ghabbour, H. A., Fun, H.-K. & Chia, T. S. (2012). Acta Cryst. E68, o1345–o1346. [DOI] [PMC free article] [PubMed]
- Farrugia, L. J. (2012). J. Appl. Cryst.45, 849–854.
- Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
- Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem.42, 235–242. [DOI] [PubMed]
- Karanth, S. N., Narayana, B., Sarojini, B. K., Kumar, S. M. & Byrappa, K. (2019). Chem. Data Collect.19, 100179.
- Kumar, R., Hussain, S., Khan, K. M., Perveen, S. & Yousuf, S. (2017). Acta Cryst. E73, 524–527. [DOI] [PMC free article] [PubMed]
- Palaska, E., Şahin, G., Kelicen, P., Durlu, N. T. & Altinok, G. (2002). Farmaco57, 101–107. [DOI] [PubMed]
- Patel, K. D., Prajapati, S. M., Panchal, S. N. & Patel, H. D. (2014). Synth. Commun.44, 1859–1875.
- Pugh, D. S., Wood, N. J., Whitwood, A. C., Parker, R. R., Mills, A. L. F., Aspell, A. M., Coyne, E., Hill, I. A. & Latter, R. C. (2019). CSD Communication (refcode ZOVPOS). CCDC, Cambridge, England.
- Salahuddin, A. M., Mazumder, A., Yar, M. S., Mazumder, R., Chakraborthy, G. S., Ahsan, M. J. & Rahman, M. U. (2017). Synth. Commun.47, 1805–1847.
- Shalaby, M. A., Rizk, S. A. & Fahim, A. M. (2023). Org. Biomol. Chem.21, 5317–5346. [DOI] [PubMed]
- Sharma, P., Subbulakshmi, K. N., Narayana, B., Sarojini, B. K. & Kant, R. (2016). Crystallogr. Rep.61, 230–233.
- Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
- Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
- Shih, M. H. (2004). Synthesis 26–32.
- Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst.54, 1006–1011. [DOI] [PMC free article] [PubMed]
- Sweeting, S. G., Hall, C. L., Potticary, J., Pridmore, N. E., Warren, S. D., Cremeens, M. E., D’Ambruoso, G. D., Matsumoto, M. & Hall, S. R. (2020). Acta Cryst. B76, 13–17. [DOI] [PubMed]
- Zhang, Q. L., Sun, L. T., Yang, X. J., Zu, H., Li, L. L., Yang, X. S. & Hu, W. (2021). Wuji Huaxue Xuebao37, 989–994.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989026008819/yz2084sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989026008819/yz2084Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989026008819/yz2084Isup3.cml
CCDC reference: 2583252
Additional supporting information: crystallographic information; 3D view; checkCIF report