Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzyl­sulfan­yl)-5-[4-(di­methyl­amino)­phen­yl]-1,3,4-oxa­diazole and 2-[(2-chloro-6-fluoro­benz­yl)sulfan­yl]-5-[4-(di­methyl­amino)­phen­yl]-1,3,4-oxa­diazole

Okmanov, R.Y.; Ziyaev, A.A.; Abdukarimov, A.S.; Toshmurodov, T.T.; Kholikov, T.S.

doi:10.1107/S2056989023004164

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 6| June 2023| Pages 552-556

https://doi.org/10.1107/S2056989023004164

Open

access

Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole

Rasul Ya. Okmanov,^a,^b ^* Abdukhakim A. Ziyaev,^a Azimboy Sh. Abdukarimov,^b Turdibek T. Toshmurodov ^a and Tursunali S. Kholikov ^b

^aS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent, 100170, Uzbekistan, and ^bNational University of Uzbekistan named after Mirzo Ulugbek, University Str. 4, Tashkent, 100174, Uzbekistan
^*Correspondence e-mail: raxul@mail.ru

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 5 April 2023; accepted 12 May 2023; online 19 May 2023)

The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C₁₇H₁₇N₃OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C₁₇H₁₅ClFN₃OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H⋯π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H⋯H and H⋯C/C⋯H interactions make the most important contributions to the crystal packing.

Keywords: synthesis; 1,3,4-oxadiazole; crystal structure; Hirshfeld surface analysis.

CCDC references: 2262491; 2262490

1. Chemical context

For the synthesis of pharmacologically active heterocyclic compounds, a study of the relationship between structure and activity is of great interest. The various five-membered aromatic heterocyclic compounds have a diverse range of action. These include oxadiazoles, consisting of two carbon atoms, two nitrogen atoms and one oxygen atom, which have four different isomeric structures: 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole.

There is much information in the literature indicating that 1,3,4-oxadiazole compounds or substituted 1,3,4-oxadiazoles have a wide spectrum of biological activity (Şahin et al., 2002 ; Erensoy et al., 2020 ; Glomb & Świątek, 2021 ) with substituted 5-aryl-1,3,4-oxadiazole-2(3H)thiones exhibiting anti-inflammatory, anti-cancer, analgesic and anticonvulsant activity (Chen et al., 2007 ; Zheng et al., 2010 ; Mamatha et al., 2019 ; Pathak et al., 2020 ). In this article, we report the synthesis and structure of two S-derivatives of 5-aryl-1,3,4-oxadiazole-2-thiole derivatives. From the reaction of 5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiole with benzyl chloride or 2-chloro-6-fluorobenzyl chloride, the corresponding S-products, 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole (I) and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole (II) were obtained in high yield.

2. Structural commentary

Compound (I) crystallizes in space group Ia. The crystal studied was refined as an inversion twin with matrix [ $[\overline{1}]$ 0 0, 0 $[\overline{1}]$ 0, 0 0 $[\overline{1}]$ ] ; the resulting BASF value is 0.43 (2). Compound (II) crystallizes in P21₁/c.

In compounds (I) and (II), the oxadiazole rings (centroid Cg1) are almost coplanar with the attached benzene (C1A–C6A, centroid Cg2) rings, forming dihedral angles of 3.36 (18) and 2.93 (14)°, respectively (Figs. 1 and 2). Such an arrangement of the benzene or phenyl fragment is also observed in many similar structures (Singh et al., 2007 ; Zareef et al., 2008 ; Zheng et al., 2010; Ji & Xu 2011 ; Zou et al., 2020 ). This arrangement indicates conjugation of π-electrons between the benzene and the 1,3,4-oxadiazole rings.

Figure 1
The asymmetric unit of (I)

with atom labeling. Ellipsoids represent 30% probability levels.

Figure 2
The asymmetric unit of (II)

with atom labeling. Ellipsoids represent 30% probability levels.

The bond angle C2—S1—C7B is 99.79 (16)° in (I) and 100.11 (10)° in (II). The dihedral angle subtended by the benzene (C1B–C6B, centroid Cg3) and 1,3,4-oxadiazole rings is 74.94 (10)° in (I) and 73.12 (7)°in (II).

3. Supramolecular features

In crystal structures of the title compounds, weak intermolecular contacts of the C—X⋯π type are observed. In (I), weak C7A—H7AC⋯Cg2 interactions link the molecules, forming infinite chains along the b-axis direction (Fig. 3). Between these chains, other interactions of the C7B—H7BA⋯Cg3 type are observed, which consolidate the crystal structure (Table 1). In the crystal structure of (II), the formation of an infinite chain is also observed as a result of the C2B—Cl1⋯Cg1 interaction, which links molecules along the c-axis direction (Fig. 4). Intermolecular C8A—H8AB⋯Cg3 and C7B—H7BA⋯Cg3 interactions between these chains consolidate the crystal structure (Table 2).

Table 1
Hydrogen-bond geometry (Å, °) for (I)

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7AC⋯Cg2ⁱ	0.96	2.80	3.626 (4)	145
C7B—H7BA⋯Cg3ⁱⁱ	0.97	2.93	3.738 (4)	141
Symmetry codes: (i) ; (ii) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °) for (II)

Cg1 and Cg3 are the centroids of the O1/C2/N3/N4/C5 and C1B–C6B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2B—Cl1⋯Cg1ⁱ	1.74 (1)	3.30 (1)	4.939 (2)	156 (1)
C8A—H8AB⋯Cg3ⁱⁱ	0.96	2.94	3.857 (3)	161
C7B—H7BA⋯Cg3ⁱⁱⁱ	0.97	2.85	3.674 (2)	143
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) ; (iii) .

Figure 3
Observed weak intermolecular C7A—H7AC⋯Cg2 interactions in the crystal structure of (I)

(the molecules are linked along the b-axis direction).

Figure 4
Observed intermolecular C2B—Cl1⋯Cg1 interactions in the crystal structure of (II)

(the molecules are linked along the c-axis direction).

In order to visualize and quantify the intermolecular interactions in (I) and (II), a Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ) was performed with Crystal Explorer 21 (Spackman et al., 2021 ) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) generated. The Hirshfeld surfaces for the molecules in (I) and (II) are shown in Figs. 5 and 6 in which the two-dimensional fingerprint plots of the most dominant contacts are also presented.

Figure 5
Three-dimensional Hirshfeld surfaces of compound (I)

plotted over d_norm in the range 0.0145 to 1.3066 a.u. Hirshfeld fingerprint plots for all contacts and decomposed into H⋯H, H⋯C/C⋯H, H⋯N/N⋯H, H⋯S/S⋯H, C⋯C and H⋯O/O⋯H contacts. d_i and d_e denote the closest internal and external distances (in Å) from a point on the surface.

Figure 6
Three-dimensional Hirshfeld surfaces of the compound (II)

plotted over d_norm in the range −0.0964 to 1.2943 a.u. Hirshfeld fingerprint plots for all contacts and decomposed into H⋯H, H⋯C/C⋯H, H⋯N/N⋯H, H⋯F/F⋯H, H⋯S/S⋯H, H⋯Cl/Cl⋯H, H⋯O/O⋯H and C⋯C contacts. d_i and d_e denote the closest internal and external distances (in Å) from a point on the surface.

For structure (I), H⋯H contacts are responsible for the largest contribution (47.8%) to the Hirshfeld surface. Besides these contacts, H⋯C/C⋯H (20.5%), H⋯N/N⋯H (12.4%), H⋯S/S⋯H (7.2%), C⋯C (4.1%) and H⋯O/O⋯H (3.5%) interactions contribute significantly to the total Hirshfeld surface (Fig. 5). The contributions of other contacts are O⋯C/C⋯O (2.0%), O⋯S/S⋯O (1.3%), S⋯C/C⋯S (0.9%), N⋯C/C⋯N (0.4%) and N⋯N (0.1%).

In the structure of (II), the percentage contributions of the most significant contacts differ because of the presence of H⋯F/F⋯H and H⋯Cl/Cl⋯H interactions and amount to H⋯H (31.8%), H⋯C/C⋯H (20.0%), H⋯N/N⋯H (9.8%), H⋯F/F⋯H (7.5%), H⋯S/S⋯H (7.1%), H⋯Cl/Cl⋯H (5.7%), H⋯O/O⋯H (5.0%) and C⋯C (3.9%) (Fig. 6). The contributions of other contacts are Cl⋯C/C⋯Cl (2.8%), Cl⋯F/F⋯Cl (1.4%), N⋯S/S⋯N (1.0%), Cl⋯O/O⋯Cl (0.9%), O⋯C/C⋯O (0.4%), N⋯C/C⋯N (0.4%), S⋯Cl/Cl⋯S (0.3%), S⋯C/C⋯S (0.3%) and N⋯O/O⋯N (0.2%).

As seen from Figs. 5 and 6, the most significant contributions to the overall Hirshfeld surface in the crystal structures of (I) and (II) are from H⋯H and H⋯C/C⋯H contacts (together they amount to more than 50% for both cases).

4. Database survey

A search in the Cambridge Structural Database (CSD, version 2022.3.0; Groom et al., 2016 ) yielded 45 derivatives of 5-phenyl-1,3,4-oxadiazole-2-thiole, nine of which are 2-(benzylsulfanyl)-5-phenyl-1,3,4-oxadiazole derivatives, and no structure was found for a 5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiole derivative. When searching for similar structures in the CSD, two matches were found: 2-(4-methoxyphenyl)-5-({[3-(trifluoromethyl)phenyl] methyl}sulfanyl)-1,3,4-oxadiazole (SOXGOE; Hamdani et al., 2020 ) and 2-benzylsulfanyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole (GIDKEK; Chen et al., 2007), in which the benzene rings and 1,3,4-oxadiazole fragments are arranged in a similar manner as the title compounds. However, in the structures of SOXGOE and GIGKEK, intermolecular interactions are not observed, the molecules being stabilized mainly by van der Waals forces.

5. Synthesis and crystallization

A mixture of 5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiole (0.005 mol), benzyl chloride or 2-chloro-6-fluorobenzyl chloride (0.005 mol) and K₂CO₃ (0.005 mol) was boiled in 20 ml of dry acetone for 6 h. The solvent was then removed, the residue washed with water and with 2% NaOH solution to remove unreacted oxadiazolthione, and then washed with water until neutral. The resulting target products were dried in air and recrystallized from ethanol solution. Compound (I): yield 96%, m.p. 404–405 K. Compound (II): yield 92%, m.p. 406–407 K.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms were positioned geometrically (with C—H distances of 0.97 Å for CH₂, 0.96 Å for CH₃ and 0.93 Å for C_ar) and included in the refinement in a riding-motion approximation with U_iso(H) = 1.2U_eq(C) [U_iso = 1.5U_eq(C) for methyl H atoms]. For (I), the crystal studied was refined as an inversion twin with matrix [ $[\overline{1}]$ 0 0, 0 $[\overline{1}]$ 0, 0 0 $[\overline{1}]$ ] ; the resulting BASF value is 0.43 (2).

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₇H₁₇N₃OS	C₁₇H₁₅ClFN₃OS
M_r	311.39	363.83
Crystal system, space group	Monoclinic, Ia	Monoclinic, P2₁/c
Temperature (K)	297	296
a, b, c (Å)	16.816 (3), 4.7848 (10), 20.123 (4)	16.308 (3), 7.9787 (16), 13.072 (3)
β (°)	105.96 (3)	103.33 (3)
V (Å³)	1556.7 (6)	1655.1 (6)
Z	4	4
Radiation type	Cu Kα	Cu Kα
μ (mm⁻¹)	1.88	3.40
Crystal size (mm)	0.35 × 0.20 × 0.15	0.30 × 0.25 × 0.15

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.749, 1.000	0.704, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6572, 2732, 2583	8579, 3181, 2771
R_int	0.026	0.021
(sin θ/λ)_max (Å⁻¹)	0.615	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.089, 1.04	0.039, 0.106, 1.05
No. of reflections	2732	3181
No. of parameters	202	219
No. of restraints	2	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21	0.18, −0.33
Absolute structure	Refined as an inversion twin	–
Absolute structure parameter	0.43 (2)	–
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97, SHELXTL (Sheldrick, 2015 ) and XP in SHELXTL (Sheldrick, 2008 ), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 2262491; 2262490

Crystal structure: contains datablocks I, II, Global. DOI: https://doi.org/10.1107/S2056989023004164/dx2051sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023004164/dx2051Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023004164/dx2051IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023004164/dx2051Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989023004164/dx2051IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

2-(Benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole (I) top

Crystal data top

C₁₇H₁₇N₃OS	F(000) = 656
M_r = 311.39	D_x = 1.329 Mg m⁻³
Monoclinic, Ia	Cu Kα radiation, λ = 1.54184 Å
a = 16.816 (3) Å	Cell parameters from 4218 reflections
b = 4.7848 (10) Å	θ = 3.0–71.2°
c = 20.123 (4) Å	µ = 1.88 mm⁻¹
β = 105.96 (3)°	T = 297 K
V = 1556.7 (6) Å³	Prizmatic, colorless
Z = 4	0.35 × 0.20 × 0.15 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	2732 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2583 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.026
ω scans	θ_max = 71.5°, θ_min = 4.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −20→20
T_min = 0.749, T_max = 1.000	k = −5→5
6572 measured reflections	l = −24→24

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0541P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.15 e Å⁻³
2732 reflections	Δρ_min = −0.21 e Å⁻³
202 parameters	Absolute structure: Refined as an inversion twin
2 restraints	Absolute structure parameter: 0.43 (2)
Primary atom site location: dual

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.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
S1	0.35188 (5)	0.65967 (15)	0.24394 (4)	0.0675 (2)
O1	0.38557 (12)	0.2829 (4)	0.15990 (10)	0.0546 (4)
N3	0.25142 (15)	0.3621 (5)	0.13720 (14)	0.0607 (6)
N4	0.26466 (15)	0.1612 (5)	0.09008 (14)	0.0595 (6)
N1A	0.51675 (14)	−0.6015 (5)	−0.02778 (13)	0.0614 (6)
C2	0.32356 (17)	0.4249 (6)	0.17577 (14)	0.0561 (6)
C5	0.34386 (17)	0.1194 (6)	0.10548 (14)	0.0518 (6)
C1A	0.38914 (15)	−0.0700 (6)	0.07351 (13)	0.0497 (5)
C2A	0.34682 (16)	−0.2469 (6)	0.02095 (15)	0.0541 (6)
H2AA	0.289305	−0.245654	0.007619	0.065*
C3A	0.38831 (17)	−0.4238 (6)	−0.01174 (14)	0.0543 (6)
H3AA	0.358087	−0.539335	−0.046814	0.065*
C4A	0.47522 (16)	−0.4349 (6)	0.00637 (14)	0.0514 (6)
C5A	0.51775 (17)	−0.2603 (6)	0.06167 (16)	0.0555 (6)
H5AA	0.575192	−0.266824	0.076730	0.067*
C6A	0.47585 (16)	−0.0824 (6)	0.09332 (14)	0.0549 (6)
H6AA	0.505497	0.032849	0.128737	0.066*
C7A	0.4722 (2)	−0.7707 (7)	−0.08530 (18)	0.0681 (8)
H7AA	0.510695	−0.863023	−0.105354	0.102*
H7AB	0.436148	−0.653916	−0.119410	0.102*
H7AC	0.439939	−0.907932	−0.069428	0.102*
C8A	0.60506 (19)	−0.6514 (7)	0.0000 (2)	0.0718 (9)
H8AA	0.622912	−0.784539	−0.028621	0.108*
H8AB	0.615965	−0.723417	0.046118	0.108*
H8AC	0.634547	−0.479131	0.000665	0.108*
C1B	0.20329 (17)	0.5859 (6)	0.27839 (14)	0.0536 (6)
C2B	0.23312 (18)	0.5105 (7)	0.34681 (15)	0.0605 (7)
H2BA	0.283977	0.579459	0.372557	0.073*
C3B	0.1890 (2)	0.3346 (7)	0.37792 (18)	0.0723 (9)
H3BA	0.209881	0.285927	0.424205	0.087*
C4B	0.1137 (3)	0.2317 (9)	0.3397 (2)	0.0826 (10)
H4BA	0.083364	0.114435	0.360365	0.099*
C5B	0.0837 (2)	0.3010 (10)	0.2720 (2)	0.0863 (11)
H5BA	0.033294	0.228498	0.246285	0.104*
C6B	0.1276 (2)	0.4787 (8)	0.24093 (17)	0.0710 (8)
H6BA	0.106285	0.526586	0.194651	0.085*
C7B	0.2500 (2)	0.7858 (6)	0.24513 (19)	0.0687 (8)
H7BA	0.256392	0.962089	0.269826	0.082*
H7BB	0.217555	0.820846	0.197995	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0666 (4)	0.0746 (4)	0.0645 (4)	−0.0124 (4)	0.0234 (3)	−0.0030 (4)
O1	0.0501 (10)	0.0581 (9)	0.0555 (10)	−0.0021 (8)	0.0144 (8)	0.0069 (8)
N3	0.0516 (12)	0.0674 (14)	0.0641 (14)	0.0038 (10)	0.0177 (11)	0.0037 (11)
N4	0.0465 (12)	0.0681 (14)	0.0619 (14)	0.0035 (10)	0.0116 (10)	0.0036 (11)
N1A	0.0471 (12)	0.0666 (14)	0.0680 (15)	−0.0002 (10)	0.0114 (11)	−0.0029 (11)
C2	0.0564 (16)	0.0568 (14)	0.0578 (15)	−0.0004 (11)	0.0201 (13)	0.0116 (12)
C5	0.0471 (13)	0.0552 (13)	0.0515 (14)	−0.0025 (11)	0.0108 (11)	0.0121 (11)
C1A	0.0448 (12)	0.0528 (12)	0.0506 (13)	0.0000 (10)	0.0115 (11)	0.0127 (10)
C2A	0.0398 (13)	0.0597 (14)	0.0601 (15)	−0.0042 (10)	0.0092 (11)	0.0115 (12)
C3A	0.0451 (13)	0.0565 (14)	0.0571 (15)	−0.0047 (11)	0.0069 (11)	0.0061 (12)
C4A	0.0438 (12)	0.0521 (13)	0.0556 (15)	−0.0040 (10)	0.0091 (11)	0.0119 (11)
C5A	0.0400 (12)	0.0612 (14)	0.0600 (15)	−0.0034 (11)	0.0048 (12)	0.0073 (12)
C6A	0.0469 (13)	0.0576 (14)	0.0552 (14)	−0.0041 (11)	0.0058 (11)	0.0041 (12)
C7A	0.0636 (18)	0.0708 (18)	0.0676 (19)	−0.0046 (15)	0.0145 (15)	−0.0064 (15)
C8A	0.0473 (15)	0.084 (2)	0.084 (2)	0.0032 (15)	0.0178 (15)	−0.0042 (17)
C1B	0.0555 (14)	0.0531 (13)	0.0541 (14)	0.0088 (11)	0.0184 (12)	−0.0046 (11)
C2B	0.0550 (15)	0.0725 (17)	0.0527 (15)	−0.0006 (13)	0.0126 (12)	−0.0028 (12)
C3B	0.071 (2)	0.089 (2)	0.0609 (18)	0.0056 (16)	0.0252 (16)	0.0073 (15)
C4B	0.074 (2)	0.101 (3)	0.084 (2)	−0.0115 (19)	0.042 (2)	−0.006 (2)
C5B	0.0556 (18)	0.119 (3)	0.087 (2)	−0.0168 (18)	0.0245 (17)	−0.027 (2)
C6B	0.0580 (16)	0.097 (2)	0.0563 (17)	0.0077 (16)	0.0121 (14)	−0.0097 (16)
C7B	0.083 (2)	0.0529 (15)	0.0729 (19)	0.0070 (14)	0.0255 (16)	0.0060 (13)

Geometric parameters (Å, º) top

S1—C2	1.735 (3)	C7A—H7AA	0.9600
S1—C7B	1.823 (4)	C7A—H7AB	0.9600
O1—C2	1.354 (3)	C7A—H7AC	0.9600
O1—C5	1.371 (3)	C8A—H8AA	0.9600
N3—C2	1.283 (4)	C8A—H8AB	0.9600
N3—N4	1.410 (4)	C8A—H8AC	0.9600
N4—C5	1.297 (4)	C1B—C2B	1.378 (4)
N1A—C4A	1.364 (4)	C1B—C6B	1.387 (5)
N1A—C7A	1.442 (4)	C1B—C7B	1.506 (5)
N1A—C8A	1.455 (4)	C2B—C3B	1.381 (5)
C5—C1A	1.444 (4)	C2B—H2BA	0.9300
C1A—C2A	1.388 (4)	C3B—C4B	1.379 (6)
C1A—C6A	1.403 (4)	C3B—H3BA	0.9300
C2A—C3A	1.374 (4)	C4B—C5B	1.358 (7)
C2A—H2AA	0.9300	C4B—H4BA	0.9300
C3A—C4A	1.407 (4)	C5B—C6B	1.383 (6)
C3A—H3AA	0.9300	C5B—H5BA	0.9300
C4A—C5A	1.418 (4)	C6B—H6BA	0.9300
C5A—C6A	1.369 (4)	C7B—H7BA	0.9700
C5A—H5AA	0.9300	C7B—H7BB	0.9700
C6A—H6AA	0.9300

C2—S1—C7B	99.79 (16)	N1A—C7A—H7AC	109.5
C2—O1—C5	102.5 (2)	H7AA—C7A—H7AC	109.5
C2—N3—N4	105.6 (2)	H7AB—C7A—H7AC	109.5
C5—N4—N3	106.6 (2)	N1A—C8A—H8AA	109.5
C4A—N1A—C7A	120.5 (2)	N1A—C8A—H8AB	109.5
C4A—N1A—C8A	120.8 (3)	H8AA—C8A—H8AB	109.5
C7A—N1A—C8A	117.8 (3)	N1A—C8A—H8AC	109.5
N3—C2—O1	113.6 (3)	H8AA—C8A—H8AC	109.5
N3—C2—S1	129.6 (2)	H8AB—C8A—H8AC	109.5
O1—C2—S1	116.7 (2)	C2B—C1B—C6B	118.3 (3)
N4—C5—O1	111.6 (3)	C2B—C1B—C7B	121.3 (3)
N4—C5—C1A	128.5 (3)	C6B—C1B—C7B	120.4 (3)
O1—C5—C1A	119.8 (2)	C1B—C2B—C3B	121.3 (3)
C2A—C1A—C6A	117.7 (3)	C1B—C2B—H2BA	119.3
C2A—C1A—C5	120.0 (2)	C3B—C2B—H2BA	119.3
C6A—C1A—C5	122.3 (2)	C4B—C3B—C2B	119.3 (3)
C3A—C2A—C1A	121.3 (3)	C4B—C3B—H3BA	120.3
C3A—C2A—H2AA	119.4	C2B—C3B—H3BA	120.3
C1A—C2A—H2AA	119.4	C5B—C4B—C3B	120.2 (4)
C2A—C3A—C4A	121.8 (3)	C5B—C4B—H4BA	119.9
C2A—C3A—H3AA	119.1	C3B—C4B—H4BA	119.9
C4A—C3A—H3AA	119.1	C4B—C5B—C6B	120.4 (4)
N1A—C4A—C3A	122.1 (3)	C4B—C5B—H5BA	119.8
N1A—C4A—C5A	121.5 (2)	C6B—C5B—H5BA	119.8
C3A—C4A—C5A	116.4 (3)	C5B—C6B—C1B	120.4 (3)
C6A—C5A—C4A	121.2 (3)	C5B—C6B—H6BA	119.8
C6A—C5A—H5AA	119.4	C1B—C6B—H6BA	119.8
C4A—C5A—H5AA	119.4	C1B—C7B—S1	113.7 (2)
C5A—C6A—C1A	121.4 (3)	C1B—C7B—H7BA	108.8
C5A—C6A—H6AA	119.3	S1—C7B—H7BA	108.8
C1A—C6A—H6AA	119.3	C1B—C7B—H7BB	108.8
N1A—C7A—H7AA	109.5	S1—C7B—H7BB	108.8
N1A—C7A—H7AB	109.5	H7BA—C7B—H7BB	107.7
H7AA—C7A—H7AB	109.5

C2—N3—N4—C5	0.8 (3)	C7A—N1A—C4A—C5A	−178.0 (3)
N4—N3—C2—O1	−0.6 (3)	C8A—N1A—C4A—C5A	13.0 (4)
N4—N3—C2—S1	179.7 (2)	C2A—C3A—C4A—N1A	−177.2 (3)
C5—O1—C2—N3	0.2 (3)	C2A—C3A—C4A—C5A	2.0 (4)
C5—O1—C2—S1	179.95 (18)	N1A—C4A—C5A—C6A	176.4 (3)
C7B—S1—C2—N3	0.7 (3)	C3A—C4A—C5A—C6A	−2.8 (4)
C7B—S1—C2—O1	−179.1 (2)	C4A—C5A—C6A—C1A	1.5 (4)
N3—N4—C5—O1	−0.8 (3)	C2A—C1A—C6A—C5A	0.6 (4)
N3—N4—C5—C1A	178.9 (2)	C5—C1A—C6A—C5A	−179.0 (3)
C2—O1—C5—N4	0.4 (3)	C6B—C1B—C2B—C3B	−0.5 (4)
C2—O1—C5—C1A	−179.3 (2)	C7B—C1B—C2B—C3B	177.8 (3)
N4—C5—C1A—C2A	−3.2 (4)	C1B—C2B—C3B—C4B	0.2 (5)
O1—C5—C1A—C2A	176.4 (2)	C2B—C3B—C4B—C5B	0.6 (6)
N4—C5—C1A—C6A	176.4 (3)	C3B—C4B—C5B—C6B	−1.0 (6)
O1—C5—C1A—C6A	−4.0 (4)	C4B—C5B—C6B—C1B	0.7 (6)
C6A—C1A—C2A—C3A	−1.5 (4)	C2B—C1B—C6B—C5B	0.1 (5)
C5—C1A—C2A—C3A	178.2 (2)	C7B—C1B—C6B—C5B	−178.3 (3)
C1A—C2A—C3A—C4A	0.1 (4)	C2B—C1B—C7B—S1	61.9 (3)
C7A—N1A—C4A—C3A	1.1 (4)	C6B—C1B—C7B—S1	−119.8 (3)
C8A—N1A—C4A—C3A	−167.9 (3)	C2—S1—C7B—C1B	77.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AC···Cg2ⁱ	0.96	2.80	3.626 (4)	145
C7B—H7BA···Cg3ⁱⁱ	0.97	2.93	3.738 (4)	141

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

2-[(2-Chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole (II) top

Crystal data top

C₁₇H₁₅ClFN₃OS	F(000) = 752
M_r = 363.83	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 16.308 (3) Å	Cell parameters from 4884 reflections
b = 7.9787 (16) Å	θ = 2.8–70.7°
c = 13.072 (3) Å	µ = 3.40 mm⁻¹
β = 103.33 (3)°	T = 296 K
V = 1655.1 (6) Å³	Prizmatic, colorless
Z = 4	0.30 × 0.25 × 0.15 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	3181 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2771 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.021
ω scans	θ_max = 71.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −19→19
T_min = 0.704, T_max = 1.000	k = −9→9
8579 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0548P)² + 0.3561P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3181 reflections	Δρ_max = 0.18 e Å⁻³
219 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.70024 (3)	0.25638 (6)	0.67262 (4)	0.05766 (17)
F1	0.53784 (8)	0.62390 (19)	0.74016 (9)	0.0710 (4)
Cl1	0.65329 (4)	0.42921 (8)	0.43372 (4)	0.07189 (19)
N3	0.70438 (10)	0.4438 (2)	0.85013 (13)	0.0575 (4)
N4	0.76430 (11)	0.4635 (2)	0.94693 (13)	0.0591 (4)
N4A	1.13318 (11)	0.2937 (3)	1.24513 (14)	0.0645 (5)
O1	0.81509 (8)	0.28552 (16)	0.84836 (9)	0.0484 (3)
C2	0.73729 (11)	0.3394 (2)	0.79712 (14)	0.0469 (4)
C5	0.82736 (11)	0.3695 (2)	0.94229 (13)	0.0459 (4)
C1A	0.90528 (11)	0.3437 (2)	1.02033 (13)	0.0458 (4)
C2A	0.91795 (13)	0.4247 (3)	1.11650 (15)	0.0569 (5)
H2AA	0.875254	0.491431	1.130992	0.068*
C3A	0.99218 (13)	0.4085 (3)	1.19079 (15)	0.0583 (5)
H3AA	0.998800	0.464500	1.254560	0.070*
C4A	1.05833 (11)	0.3090 (2)	1.17239 (14)	0.0490 (4)
C5A	1.04385 (13)	0.2249 (3)	1.07595 (16)	0.0583 (5)
H5AA	1.085423	0.154883	1.061691	0.070*
C6A	0.96948 (13)	0.2437 (3)	1.00180 (15)	0.0560 (5)
H6AA	0.962246	0.187883	0.937881	0.067*
C7A	1.14655 (15)	0.3781 (4)	1.34498 (18)	0.0783 (7)
H7AA	1.103965	0.344344	1.380639	0.118*
H7AB	1.143475	0.497119	1.333810	0.118*
H7AC	1.201117	0.349276	1.387036	0.118*
C8A	1.20022 (14)	0.1914 (3)	1.2238 (2)	0.0734 (6)
H8AA	1.180549	0.078396	1.209806	0.110*
H8AB	1.247110	0.192586	1.283686	0.110*
H8AC	1.217624	0.234985	1.163709	0.110*
C1B	0.59678 (10)	0.5336 (2)	0.60183 (12)	0.0413 (4)
C2B	0.62301 (10)	0.5823 (2)	0.51172 (13)	0.0447 (4)
C3B	0.62432 (12)	0.7473 (3)	0.48082 (16)	0.0555 (5)
H3BA	0.643266	0.775274	0.421154	0.067*
C4B	0.59745 (14)	0.8693 (3)	0.53885 (19)	0.0641 (6)
H4BA	0.598734	0.980957	0.518853	0.077*
C5B	0.56857 (13)	0.8285 (3)	0.62650 (18)	0.0618 (5)
H5BA	0.549420	0.911110	0.665483	0.074*
C6B	0.56865 (11)	0.6628 (3)	0.65515 (14)	0.0487 (4)
C7B	0.59662 (12)	0.3548 (2)	0.63726 (16)	0.0537 (5)
H7BA	0.561130	0.289986	0.581406	0.064*
H7BB	0.571488	0.350251	0.697611	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0609 (3)	0.0489 (3)	0.0553 (3)	0.0077 (2)	−0.0030 (2)	−0.0039 (2)
F1	0.0611 (7)	0.1044 (10)	0.0511 (6)	0.0122 (7)	0.0199 (5)	−0.0031 (6)
Cl1	0.0721 (4)	0.0899 (4)	0.0532 (3)	0.0172 (3)	0.0134 (2)	−0.0173 (3)
N3	0.0510 (9)	0.0600 (10)	0.0562 (9)	0.0113 (8)	0.0010 (7)	0.0001 (8)
N4	0.0550 (9)	0.0651 (10)	0.0532 (9)	0.0145 (8)	0.0046 (7)	−0.0054 (8)
N4A	0.0483 (9)	0.0850 (12)	0.0551 (9)	0.0034 (9)	0.0013 (7)	0.0009 (9)
O1	0.0478 (7)	0.0486 (7)	0.0460 (6)	0.0071 (5)	0.0050 (5)	−0.0008 (5)
C2	0.0466 (9)	0.0408 (9)	0.0500 (9)	0.0025 (8)	0.0043 (8)	0.0053 (7)
C5	0.0481 (10)	0.0438 (9)	0.0455 (9)	0.0032 (8)	0.0102 (7)	0.0005 (7)
C1A	0.0454 (9)	0.0463 (9)	0.0447 (9)	0.0038 (8)	0.0088 (7)	0.0015 (7)
C2A	0.0552 (11)	0.0628 (12)	0.0518 (10)	0.0154 (9)	0.0107 (9)	−0.0077 (9)
C3A	0.0636 (12)	0.0639 (12)	0.0449 (10)	0.0076 (10)	0.0072 (9)	−0.0093 (9)
C4A	0.0459 (10)	0.0549 (10)	0.0454 (9)	−0.0020 (8)	0.0093 (7)	0.0066 (8)
C5A	0.0504 (11)	0.0717 (13)	0.0524 (10)	0.0171 (10)	0.0110 (9)	−0.0048 (9)
C6A	0.0560 (11)	0.0650 (12)	0.0455 (10)	0.0124 (9)	0.0087 (9)	−0.0080 (9)
C7A	0.0620 (13)	0.109 (2)	0.0565 (12)	−0.0168 (14)	−0.0021 (10)	−0.0042 (13)
C8A	0.0484 (11)	0.0855 (16)	0.0824 (15)	0.0075 (11)	0.0071 (10)	0.0184 (13)
C1B	0.0319 (8)	0.0469 (9)	0.0415 (8)	−0.0017 (7)	0.0008 (6)	−0.0021 (7)
C2B	0.0340 (8)	0.0545 (10)	0.0423 (8)	0.0003 (7)	0.0018 (7)	−0.0044 (7)
C3B	0.0431 (10)	0.0641 (12)	0.0553 (11)	−0.0049 (9)	0.0031 (8)	0.0125 (9)
C4B	0.0555 (12)	0.0470 (11)	0.0818 (15)	−0.0011 (9)	−0.0005 (10)	0.0053 (10)
C5B	0.0522 (11)	0.0545 (11)	0.0731 (13)	0.0080 (9)	0.0032 (10)	−0.0161 (10)
C6B	0.0367 (8)	0.0633 (11)	0.0437 (9)	0.0029 (8)	0.0048 (7)	−0.0064 (8)
C7B	0.0448 (10)	0.0522 (10)	0.0589 (11)	−0.0064 (8)	0.0014 (8)	0.0019 (8)

Geometric parameters (Å, º) top

S1—C2	1.7317 (19)	C5A—H5AA	0.9300
S1—C7B	1.824 (2)	C6A—H6AA	0.9300
F1—C6B	1.357 (2)	C7A—H7AA	0.9600
Cl1—C2B	1.7346 (18)	C7A—H7AB	0.9600
N3—C2	1.278 (2)	C7A—H7AC	0.9600
N3—N4	1.418 (2)	C8A—H8AA	0.9600
N4—C5	1.286 (2)	C8A—H8AB	0.9600
N4A—C4A	1.369 (2)	C8A—H8AC	0.9600
N4A—C7A	1.440 (3)	C1B—C6B	1.381 (2)
N4A—C8A	1.442 (3)	C1B—C2B	1.398 (2)
O1—C2	1.361 (2)	C1B—C7B	1.500 (2)
O1—C5	1.372 (2)	C2B—C3B	1.378 (3)
C5—C1A	1.449 (2)	C3B—C4B	1.367 (3)
C1A—C6A	1.382 (3)	C3B—H3BA	0.9300
C1A—C2A	1.386 (3)	C4B—C5B	1.375 (3)
C2A—C3A	1.372 (3)	C4B—H4BA	0.9300
C2A—H2AA	0.9300	C5B—C6B	1.374 (3)
C3A—C4A	1.404 (3)	C5B—H5BA	0.9300
C3A—H3AA	0.9300	C7B—H7BA	0.9700
C4A—C5A	1.399 (3)	C7B—H7BB	0.9700
C5A—C6A	1.375 (3)

C2—S1—C7B	100.11 (10)	N4A—C7A—H7AC	109.5
C2—N3—N4	105.48 (15)	H7AA—C7A—H7AC	109.5
C5—N4—N3	106.70 (15)	H7AB—C7A—H7AC	109.5
C4A—N4A—C7A	120.80 (19)	N4A—C8A—H8AA	109.5
C4A—N4A—C8A	120.70 (19)	N4A—C8A—H8AB	109.5
C7A—N4A—C8A	118.50 (19)	H8AA—C8A—H8AB	109.5
C2—O1—C5	102.31 (14)	N4A—C8A—H8AC	109.5
N3—C2—O1	113.54 (16)	H8AA—C8A—H8AC	109.5
N3—C2—S1	131.27 (14)	H8AB—C8A—H8AC	109.5
O1—C2—S1	115.19 (13)	C6B—C1B—C2B	114.82 (16)
N4—C5—O1	111.96 (16)	C6B—C1B—C7B	121.99 (17)
N4—C5—C1A	129.11 (17)	C2B—C1B—C7B	123.18 (16)
O1—C5—C1A	118.93 (15)	C3B—C2B—C1B	122.74 (17)
C6A—C1A—C2A	117.89 (17)	C3B—C2B—Cl1	118.33 (15)
C6A—C1A—C5	122.38 (16)	C1B—C2B—Cl1	118.91 (14)
C2A—C1A—C5	119.70 (17)	C4B—C3B—C2B	119.26 (19)
C3A—C2A—C1A	121.37 (18)	C4B—C3B—H3BA	120.4
C3A—C2A—H2AA	119.3	C2B—C3B—H3BA	120.4
C1A—C2A—H2AA	119.3	C3B—C4B—C5B	120.6 (2)
C2A—C3A—C4A	121.29 (18)	C3B—C4B—H4BA	119.7
C2A—C3A—H3AA	119.4	C5B—C4B—H4BA	119.7
C4A—C3A—H3AA	119.4	C6B—C5B—C4B	118.43 (19)
N4A—C4A—C5A	121.42 (18)	C6B—C5B—H5BA	120.8
N4A—C4A—C3A	121.92 (18)	C4B—C5B—H5BA	120.8
C5A—C4A—C3A	116.66 (17)	F1—C6B—C5B	117.80 (18)
C6A—C5A—C4A	121.41 (18)	F1—C6B—C1B	118.12 (18)
C6A—C5A—H5AA	119.3	C5B—C6B—C1B	124.07 (18)
C4A—C5A—H5AA	119.3	C1B—C7B—S1	114.87 (13)
C5A—C6A—C1A	121.35 (18)	C1B—C7B—H7BA	108.6
C5A—C6A—H6AA	119.3	S1—C7B—H7BA	108.6
C1A—C6A—H6AA	119.3	C1B—C7B—H7BB	108.6
N4A—C7A—H7AA	109.5	S1—C7B—H7BB	108.6
N4A—C7A—H7AB	109.5	H7BA—C7B—H7BB	107.5
H7AA—C7A—H7AB	109.5

C2—N3—N4—C5	0.2 (2)	C2A—C3A—C4A—C5A	−1.4 (3)
N4—N3—C2—O1	−0.4 (2)	N4A—C4A—C5A—C6A	−178.3 (2)
N4—N3—C2—S1	179.84 (15)	C3A—C4A—C5A—C6A	2.1 (3)
C5—O1—C2—N3	0.4 (2)	C4A—C5A—C6A—C1A	−1.3 (3)
C5—O1—C2—S1	−179.82 (12)	C2A—C1A—C6A—C5A	−0.2 (3)
C7B—S1—C2—N3	−1.9 (2)	C5—C1A—C6A—C5A	178.09 (19)
C7B—S1—C2—O1	178.28 (13)	C6B—C1B—C2B—C3B	2.8 (2)
N3—N4—C5—O1	0.0 (2)	C7B—C1B—C2B—C3B	−178.83 (17)
N3—N4—C5—C1A	179.96 (18)	C6B—C1B—C2B—Cl1	−175.93 (12)
C2—O1—C5—N4	−0.2 (2)	C7B—C1B—C2B—Cl1	2.5 (2)
C2—O1—C5—C1A	179.82 (16)	C1B—C2B—C3B—C4B	−1.3 (3)
N4—C5—C1A—C6A	−176.9 (2)	Cl1—C2B—C3B—C4B	177.37 (15)
O1—C5—C1A—C6A	3.1 (3)	C2B—C3B—C4B—C5B	−0.7 (3)
N4—C5—C1A—C2A	1.4 (3)	C3B—C4B—C5B—C6B	1.0 (3)
O1—C5—C1A—C2A	−178.60 (17)	C4B—C5B—C6B—F1	−178.26 (17)
C6A—C1A—C2A—C3A	0.9 (3)	C4B—C5B—C6B—C1B	0.6 (3)
C5—C1A—C2A—C3A	−177.46 (19)	C2B—C1B—C6B—F1	176.46 (14)
C1A—C2A—C3A—C4A	−0.1 (3)	C7B—C1B—C6B—F1	−2.0 (2)
C7A—N4A—C4A—C5A	−178.7 (2)	C2B—C1B—C6B—C5B	−2.4 (2)
C8A—N4A—C4A—C5A	0.8 (3)	C7B—C1B—C6B—C5B	179.15 (17)
C7A—N4A—C4A—C3A	0.9 (3)	C6B—C1B—C7B—S1	−118.50 (17)
C8A—N4A—C4A—C3A	−179.6 (2)	C2B—C1B—C7B—S1	63.2 (2)
C2A—C3A—C4A—N4A	179.0 (2)	C2—S1—C7B—C1B	78.87 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the O1/C2/N3/N4/C5 and C1B–C6B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2B—Cl1···Cg1ⁱ	1.74 (1)	3.30 (1)	4.939 (2)	156 (1)
C8A—H8AB···Cg3ⁱⁱ	0.96	2.94	3.857 (3)	161
C7B—H7BA···Cg3ⁱⁱⁱ	0.97	2.85	3.674 (2)	143

Symmetry codes: (i) x, −y−1/2, z−3/2; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.

Acknowledgements

We are especially grateful to Professor B. Tashkhodzhaev for help in discussing the results.

References

Chen, C. J., Song, B. A., Yang, S., Xu, G. F., Bhadury, P. S., Jin, L. H., Hu, D. Y., Li, Q. Z., Liu, F., Xue, W., Lu, P. & Chen, Z. (2007). Bioorg. Med. Chem. 15, 3981–3989. Web of Science CSD CrossRef PubMed CAS Google Scholar
Erensoy, G., Ding, K., Zhan, C. G., Elmezayen, A., Yelekçi, K., Duracik, M., Özakpinar, Ö. B. & Küçükgüzel, İ. (2020). J. Res. Pharm. 24, 436–451. CAS Google Scholar
Glomb, T. & Świątek, P. (2021). Int. J. Mol. Sci. 22, 6979–6979. CrossRef CAS PubMed Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hamdani, S. S., Khan, B. A., Ahmed, M. N., Hameed, S., Akhter, K., Ayub, K. & Mahmood, T. (2020). J. Mol. Struct. 1200, 127085–127085. CSD CrossRef Google Scholar
Ji, H. & Xu, X.-D. (2011). Acta Cryst. E67, o3490. CSD CrossRef IUCr Journals Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Mamatha, S. V., Bhat, M., Sagar, B. K. & Meenakshi, S. K. (2019). J. Mol. Struct. 1196, 186–193. Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Pathak, S., Sharma, S., Pathak, V. & Prasad, M. (2020). J. Appl. Pharm. Res. 8, 50–61. CrossRef CAS Google Scholar
Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Şahin, G., Palaska, E., Ekizoğlu, M. & Özalp, M. (2002). Farmaco, 57, 539–542. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Singh, N. K., Butcher, R. J., Tripathi, P., Srivastava, A. K. & Bharty, M. K. (2007). Acta Cryst. E63, o782–o784. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zareef, M., Iqbal, R., Arfan, M. & Parvez, M. (2008). Acta Cryst. E64, o736. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zheng, Q. Z., Zhang, X. M., Xu, Y., Cheng, K., Jiao, Q. C. & Zhu, H. L. (2010). Bioorg. Med. Chem. 18, 7836–7841. CSD CrossRef CAS PubMed Google Scholar
Zou, J., Zhao, C. L., Zhang, Q. L., Pan, L. T. & He, K. (2020). Z. Kristallogr. New Cryst. Struct. 235, 745–746. CSD CrossRef CAS Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 6| June 2023| Pages 552-556

https://doi.org/10.1107/S2056989023004164

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzyl­sulfan­yl)-5-[4-(di­methyl­amino)­phen­yl]-1,3,4-oxa­diazole and 2-[(2-chloro-6-fluoro­benz­yl)sulfan­yl]-5-[4-(di­methyl­amino)­phen­yl]-1,3,4-oxa­diazole

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole

3. Supramolecular features