Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfan­yl]-N-(2-meth­oxy­phen­yl)acetamide

Aydin, A.; Celikesir, S.T.; Akkurt, M.; Saylam, M.; Pabuccuoglu, V.

doi:10.1107/S2056989019012908

research communications

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ISSN: 2056-9890

Volume 75| Part 10| October 2019| Pages 1531-1535

https://doi.org/10.1107/S2056989019012908

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Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide

Abdullah Aydin,^a ^* Sevim Turktekin Celikesir,^b Mehmet Akkurt,^b Merve Saylam ^c and Varol Pabuccuoglu ^d

^aDepartment of Mathematics and Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Izmir Katip Celebi University, 35620 Izmir, Turkey, and ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University, 35100 Izmir, Turkey
^*Correspondence e-mail: aaydin@kastamonu.edu.tr

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 4 September 2019; accepted 18 September 2019; online 27 September 2019)

In the title compound, C₁₆H₁₄N₂O₃S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring of the methoxyphenyl group. Two intramolecular N—H⋯O and N—H⋯N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers with R²₂(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C—H⋯π and π–π-stacking interactions [centroid-to-centroid distances = 3.631 (2) and 3.631 (2) Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H⋯H (39.3%), C⋯H/H⋯C (18.0%), O⋯H/H⋯O (15.6) and S⋯H/H⋯S (10.2%) interactions.

Keywords: crystal structure; 1,3-benzoxazole ring system; dimers; hydrogen bonding; Hirshfeld surface analysis.

CCDC reference: 1954699

1. Chemical context

As a part of our ongoing research on synthesis and screening of pharmacological activities of compounds with a benzoxazole ring, which is known to produce a wide range of biological activities (Aggarwal et al., 2017 ; Gautam et al., 2012 ), we have focused on the synthesis of 3-substituted benzoxazolone-2-thione and S-substituted benzoxazole-2-thiol derivatives. It is well known that alkylation of benzoxazolone-2-thione leads to the S-alkylated derivatives instead of N-alkylated ones (Xiang et al., 2012 ; Rakse et al., 2013 ; Yurttaş et al., 2015 ). In this manner, the title compound was synthesized as a member of the target S-substituted benzoxazole-2-thiol series. The title compound is listed in the literature with registry number CASRN 331966-95-1 but corresponding scientific reference data are not available.

2. Structural commentary

In the molecular structure of the title compound (Fig. 1), the 1,3-benzoxazole ring system (N1/O1/C1–C7) is essentially planar (r.m.s deviation = 0.004 Å) and makes a dihedral angle of 66.16 (17)° with the benzene ring (C10–C15) of the methoxyphenyl group. Atoms O3 and C16 deviate from the benzene ring by −0.008 (3) and 0.099 (6) Å, respectively. The torsion angle C7—S1—C8—C9 = −87.7 (3)°, S1—C8—C9— N2 = 91.6 (4)° and C8—C9—N2—C10 = −178.8 (3)°. The C7—S1 [1.740 (4) Å] and C8—S1 [1.812 (4) Å] bond lengths are comparable with those reported for three similar structures, viz. 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(2-methylphenyl)acetamide (1.763 and 1.805 Å, respectively; Subasri et al., 2014 ), 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(2,4-dimethylphenyl)acetamide [1.7650 (14) and 1.8053 (16) Å, respectively; Choudhury et al., 2017 ] and 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(3-methoxyphenyl) acetamide [1.7721 (17) and 1.8126 (18) Å, respectively; Choudhury et al., 2017]. The two intramolecular hydrogen bonds, N2—HN2⋯O3 and N2—HN2⋯N1, form S(5) and S(7) ring motifs, respectively (Table 1, Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 benzene ring of the methoxy phenyl group.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯O3	0.86	2.22	2.608 (4)	107
N2—HN2⋯N1	0.86	2.39	3.075 (4)	136
C8—H8A⋯N1	0.97	2.48	2.914 (5)	107
C11—H11⋯O2	0.93	2.28	2.869 (5)	121
C12—H12⋯O2ⁱ	0.93	2.52	3.378 (6)	153
C13—H13⋯Cg3ⁱⁱ	0.93	2.89	3.634 (5)	138
Symmetry codes: (i) -x, -y+2, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 30% probability level. Intramolecular hydrogen bonds are shown as dashed lines.

3. Supramolecular features

In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers with $[R_{2}^{2}]$ (14) ring motifs, stacking along the b-axis direction. These dimers are linked by C—H⋯π (Table 1, Fig. 2) and π–π-stacking interactions [Fig. 2; distances of 3.631 (2) and 3.631 (2) Å between the centroids of the five- and opposite six-membered rings of the 1,3-benzoxazole ring system of adjacent molecules], forming a three-dimensional network (Fig. 3).

Figure 2
A packing diagram of the title compound, showing the intra- and intermolecular N—H⋯N and N—H⋯O, C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π-stacking interactions (dashed lines). Symmetry code: (a) − x, 2 − y, 1 − z.

Figure 3
Packing diagram of the title compound viewed down the b axis.

4. Hirshfeld surface analysis

In order to explore the role of weak intermolecular interactions in the crystal packing, Hirshfeld surfaces (d_norm) and the related two-dimensional fingerprint plots were generated using CrystalExplorer17.5 (Spackman & Jayatilaka, 2009 ; Wolff et al., 2012 ). The three-dimensional molecular Hirshfeld surfaces were generated using a high standard surface resolution over a colour scale of −0.1599 to 1.2011 a.u. for d_norm (Fig. 4). The red spots in the Hirshfeld surface represent short N⋯H/H⋯N and O⋯H/H⋯O contacts. On the shape-index surface (Fig. 5), convex blue regions represent hydrogen-donor groups and concave red regions represent hydrogen-acceptor groups. In addition, concave red regions represent C—H⋯π and π–π interactions.

Figure 4
Hirshfeld surface mapped over d_norm, showing the weak intermolecular C—H⋯O and C—H⋯C contacts.

Figure 5
View of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. Hydrogen- bond donors and acceptors are shown as blue and red regions around the atoms corresponding to positive and negative potentials, respectively.

The bright-red spots indicate their roles as the respective donors and/or acceptors; they also appear as blue and red regions corresponding to positive and negative potentials on the Hirshfeld surface mapped over electrostatic potential (Spackman et al., 2008 ) shown in Fig. 6. The blue regions indicate the positive electrostatic potential (hydrogen-bond donors), while the red regions indicate the negative electrostatic potential (hydrogen-bond acceptors).

Figure 6
Hirshfeld surfaces for the title compound, mapped with shape-index.

The two-dimensional fingerprint plots (Fig. 7) quantify the contributions of each type of intermolecular interaction to the Hirshfeld surface (McKinnon et al., 2007 ). The largest contribution (39.3% of the surface) is from H⋯H contacts (Table 2), which represent van der Waals interactions, followed by C⋯H/H⋯C contacts involved in C—H⋯π interactions (18.0%). Finally, the O⋯H/H⋯O (15.6%), S⋯H/H⋯S (10.2%) and C⋯C (4.5%) contacts correspond to hydrogen bonds and π–π interactions, respectively. The percentage contributions to the Hirshfeld surface of the various interatomic contacts are given in Table 3.

Table 2
Summary of selected short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
H5⋯O3	2.72	1 − x, 1 − y, 1 − z
S1⋯H2	3.10	x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z
C5⋯C1	3.38	1 − x, −y, 1 − z
H8B⋯C11	3.06	−x, 1 − y, 1 − z
H12⋯O2	2.52	−x, 2 − y, 1 − z
O2⋯H16A	2.74	x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
C10⋯H13	3.04	−x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
C12⋯H8A	2.82	x, 1 + y, z

Table 3
Percentage contributions of interatomic contacts to the Hirshfeld surface of the title compound

Contact	Percentage contribution
H⋯H	39.3
H⋯C/C⋯H	18.0
O⋯H/H⋯O	15.6
S⋯H/H⋯S	10.2
C⋯O/O⋯C	6.0
C⋯C	4.5
N⋯H/H⋯N	4.1
C⋯N/N⋯C	1.4
C⋯S/S⋯C	0.6
N⋯O/O⋯N	0.1

Figure 7
Hirshfeld surfaces and two-dimensional fingerprints for the compound, showing (a) all interactions and those delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) S⋯H/H⋯S and (f) C⋯O/O⋯C contacts.

5. Database survey

Related compounds to the title compound include 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(naphthalen-1-yl)acetamide (refcode JARPOK; Subasri et al., 2017 ), 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(4-fluorophenyl)acetamide (JARPUQ; Subasri et al., 2017), 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(2-methylphenyl)acetamide (GOKWIO; Subasri et al., 2014), 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(2,4-dimethylphenyl)acetamide (JAXFIA; Choudhury et al., 2017), 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(3-methoxyphenyl) acetamide (refcode: JAXFOG; Choudhury et al., 2017) and 2-[(2-aminophenyl)sulfanyl]-N-(4-methoxyphenyl)acetamide (PAXTEP; Murtaza et al., 2012 ).

In the crystals of JARPOK and JARPUQ, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers with $[R_{2}^{2}]$ (8) ring motifs. In the crystal of JARPOK, the dimers are linked by bifurcated N—H⋯(O,O) and C—H⋯O hydrogen bonds, forming layers parallel to (100). In the crystal of JARPUQ, the dimers are linked by N—H⋯O hydrogen bonds, also forming layers parallel to (100). The layers are linked by C—H⋯F hydrogen bonds, forming a three-dimensional architecture.

In the crystal of GOKWIO, molecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an $[R_{2}^{2}]$ (8) ring motif. The dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming sheets parallel to (100).

In the crystals of JAXFIA and JAXFOG, a pair of N—H⋯N hydrogen bonds links the molecules, forming inversion dimers with $[R_{2}^{2}]$ (8) ring motifs. In JAXFIA, the dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds, enclosing R₁²(14), R₁²(11) and R₁²(7) ring motifs, forming layers parallel to the (100) plane. There is also an N—H⋯π interaction present within the layer. In JAXFOG, the inversion dimers are linked by N—H⋯O hydrogen bonds enclosing an R₄⁴(18) ring motif. The presence of N—H⋯O and C—H⋯O hydrogen bonds generate an R₁²(6) ring motif. The combination of these various hydrogen bonds results in the formation of layers parallel to the (1 $[\overline{1}]$ 1) plane.

In the crystal of PAXTEP, molecules are consolidated in the form of polymeric chains along [010] as a result of N—H⋯O hydrogen bonds, which generate R₂³(18) and R₃⁴(22) loops. The polymeric chains are interlinked through C—H⋯O interaction and complete $[R_{2}^{2}]$ (8) ring motifs.

6. Synthesis and crystallization

The starting materials, 2-mercaptobenzoxazole and α-chloro-N-(o-methoxyphenyl)acetamide, were synthesized according to literature methods (Maske et al., 2012 ; Ren et al., 2015 ). For the synthesis of the title compound, 2-mercaptobenzoxazole (1 eq) and α-chloro-N-(o-methoxyphenyl) acetamide (1 eq) were heated in acetone under reflux for 1.5 h in the presence of K₂CO₃ (1 eq). The reaction mixture was then cooled to room temperature and cold water was added until precipitation was complete. The precipitate was filtered, washed with cold water and dried. The crude product was crystallized from methanol (yield 31%); m.p. 370 K.

¹H NMR (DMSO-d₆, 400 MHz) δ 3.82 (3H, s, OCH₃), δ 4.42 (2H, s, CH₂), δ 6.89 (1H, m, Ar-H), δ 7.03–7.10 (2H, m, Ar-H), δ 7.31–7.38 (2H, m, Ar-H), δ 7.62–7.68 (2H, m, Ar-H), δ 7.97 (1H, d, J = 8.4 Hz, Ar-H), δ 9.65 (1H, s, NH) p.p.m. IR v_max cm⁻¹: 3295 (NH), 1675 (amide I), 1534 (amide II); MS (ESI) m/z (intensity %): 315.32 (26) [M+H]⁺ 192.27 (100).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. All H atoms were positioned with idealized geometry and refined as riding: N—H = 0.86 Å, C—H = 0.93–0.97 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and U_iso(H) = 1.2U_eq(C, N) for all other H atoms. Thirty one outliers (13 1 3), ( $[\overline{14}]$ 1 1), (8 3 12), ( $[\overline{7}]$ 5 15), (0 3 18), (5 0 14), (14 2 5), ( $[\overline{12}]$ 0 14), ( $[\overline{2}]$ 4 17), (14 3 1), ( $[\overline{16}]$ 3 5), (1 8 4), (1 4 15), (10 5 2), ( $[\overline{5}]$ 7 8), ( $[\overline{16}]$ 0 10), (14 2 1), ( $[\overline{15}]$ 1 1), ( $[\overline{14}]$ 3 12), ( $[\overline{15}]$ 2 7), (4 1 17), (11 0 10), (15 1 2), (3 4 14), (10 2 6), ( $[\overline{5}]$ 0 18), ( $[\overline{5}]$ 3 18), ( $[\overline{1}]$ 6 11), ( $[\overline{11}]$ 5 2), (10 1 9), ( $[\overline{1}]$ 4 1 2) were omitted in the final cycles of refinement.

Table 4
Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₃S
M_r	314.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.6670 (13), 6.8704 (6), 16.7220 (16)
β (°)	108.020 (4)
V (Å³)	1493.1 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.23
Crystal size (mm)	0.10 × 0.07 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.654, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	23464, 3019, 2241
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.092, 0.169, 1.10
No. of reflections	3019
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.31
Computer programs: APEX2 and SAINT (Bruker, 2007), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/1 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1954699

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019012908/rz5264sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019012908/rz5264Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and WinGX (Farrugia, 2012).

2-[(1,3-Benzoxazol-2-yl)sulfanyl]-N-(2-methoxyphenyl)acetamide top

Crystal data top

C₁₆H₁₄N₂O₃S	F(000) = 656
M_r = 314.35	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6670 (13) Å	Cell parameters from 6692 reflections
b = 6.8704 (6) Å	θ = 3.2–26.3°
c = 16.7220 (16) Å	µ = 0.23 mm⁻¹
β = 108.020 (4)°	T = 296 K
V = 1493.1 (2) Å³	Block, colourless
Z = 4	0.10 × 0.07 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	2241 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.092
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 26.5°, θ_min = 3.1°
T_min = 0.654, T_max = 0.745	h = −17→17
23464 measured reflections	k = −8→8
3019 independent reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.092	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.0406P)² + 3.9251P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3019 reflections	Δρ_max = 0.25 e Å⁻³
200 parameters	Δρ_min = −0.31 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
C1	0.4055 (3)	0.2452 (5)	0.4388 (2)	0.0301 (9)
C2	0.4121 (3)	0.1973 (6)	0.3599 (3)	0.0437 (11)
H2	0.353578	0.186794	0.313350	0.052*
C3	0.5089 (4)	0.1660 (7)	0.3535 (3)	0.0507 (12)
H3	0.515664	0.134545	0.301349	0.061*
C4	0.5962 (4)	0.1801 (6)	0.4223 (3)	0.0515 (13)
H4	0.660182	0.158127	0.415281	0.062*
C5	0.5910 (3)	0.2258 (6)	0.5012 (3)	0.0460 (11)
H5	0.649354	0.234724	0.547961	0.055*
C6	0.4940 (3)	0.2573 (5)	0.5059 (3)	0.0330 (9)
C7	0.3608 (3)	0.3093 (5)	0.5452 (2)	0.0304 (9)
C8	0.1670 (3)	0.3513 (7)	0.5515 (3)	0.0401 (10)
H8A	0.160668	0.258715	0.506432	0.048*
H8B	0.122257	0.308919	0.583244	0.048*
C9	0.1330 (3)	0.5503 (6)	0.5143 (2)	0.0368 (10)
C10	0.1249 (3)	0.7568 (6)	0.3915 (2)	0.0272 (8)
C11	0.0683 (3)	0.9111 (6)	0.4077 (2)	0.0364 (10)
H11	0.044048	0.906129	0.453818	0.044*
C12	0.0479 (3)	1.0720 (7)	0.3557 (3)	0.0438 (11)
H12	0.008978	1.173897	0.366520	0.053*
C13	0.0844 (3)	1.0826 (7)	0.2882 (3)	0.0443 (11)
H13	0.070946	1.191980	0.253773	0.053*
C14	0.1411 (3)	0.9312 (7)	0.2714 (2)	0.0380 (10)
H14	0.165837	0.938978	0.225560	0.046*
C15	0.1615 (3)	0.7687 (6)	0.3217 (2)	0.0290 (9)
C16	0.2621 (5)	0.6219 (9)	0.2449 (3)	0.078 (2)
H16A	0.209173	0.634567	0.191795	0.118*
H16B	0.301214	0.505956	0.244719	0.118*
H16C	0.306739	0.733112	0.253872	0.118*
N1	0.3202 (2)	0.2815 (5)	0.46627 (18)	0.0309 (7)
N2	0.1476 (2)	0.5848 (5)	0.43945 (19)	0.0302 (7)
HN2	0.173630	0.491051	0.418615	0.036*
O1	0.4653 (2)	0.3005 (4)	0.57658 (16)	0.0363 (7)
O2	0.0961 (3)	0.6653 (6)	0.55175 (19)	0.0687 (11)
O3	0.2163 (2)	0.6103 (4)	0.31065 (17)	0.0467 (8)
S1	0.29895 (9)	0.35394 (17)	0.62002 (6)	0.0420 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (2)	0.0217 (18)	0.032 (2)	0.0038 (16)	0.0093 (17)	0.0053 (16)
C2	0.047 (3)	0.045 (3)	0.039 (2)	0.002 (2)	0.013 (2)	0.000 (2)
C3	0.059 (3)	0.046 (3)	0.058 (3)	0.006 (2)	0.033 (3)	0.001 (2)
C4	0.044 (3)	0.036 (2)	0.085 (4)	0.005 (2)	0.035 (3)	0.009 (2)
C5	0.032 (2)	0.035 (2)	0.066 (3)	−0.0031 (19)	0.007 (2)	0.009 (2)
C6	0.038 (2)	0.0217 (19)	0.039 (2)	−0.0024 (17)	0.0112 (18)	0.0046 (17)
C7	0.036 (2)	0.024 (2)	0.029 (2)	0.0016 (16)	0.0067 (17)	0.0061 (16)
C8	0.041 (2)	0.052 (3)	0.034 (2)	−0.009 (2)	0.0208 (19)	0.000 (2)
C9	0.036 (2)	0.053 (3)	0.026 (2)	−0.001 (2)	0.0156 (18)	−0.0053 (19)
C10	0.0190 (18)	0.040 (2)	0.0195 (18)	−0.0011 (16)	0.0007 (15)	−0.0058 (16)
C11	0.027 (2)	0.050 (3)	0.030 (2)	0.0069 (19)	0.0060 (17)	−0.0084 (19)
C12	0.035 (2)	0.049 (3)	0.040 (3)	0.017 (2)	0.002 (2)	−0.010 (2)
C13	0.043 (3)	0.044 (3)	0.038 (2)	0.012 (2)	0.000 (2)	0.005 (2)
C14	0.034 (2)	0.055 (3)	0.022 (2)	0.004 (2)	0.0055 (17)	0.0048 (19)
C15	0.0247 (19)	0.040 (2)	0.0224 (18)	0.0045 (17)	0.0067 (15)	−0.0009 (17)
C16	0.117 (5)	0.081 (4)	0.066 (4)	0.054 (4)	0.071 (4)	0.027 (3)
N1	0.0325 (18)	0.0342 (18)	0.0236 (17)	0.0008 (14)	0.0055 (14)	−0.0010 (14)
N2	0.0334 (18)	0.0369 (18)	0.0261 (16)	0.0024 (14)	0.0177 (14)	−0.0058 (14)
O1	0.0348 (16)	0.0358 (15)	0.0311 (15)	−0.0026 (13)	−0.0002 (12)	0.0042 (12)
O2	0.101 (3)	0.082 (3)	0.0401 (19)	0.035 (2)	0.046 (2)	0.0056 (18)
O3	0.062 (2)	0.0517 (19)	0.0380 (17)	0.0240 (16)	0.0333 (15)	0.0094 (14)
S1	0.0516 (7)	0.0517 (7)	0.0226 (5)	0.0004 (6)	0.0114 (5)	0.0050 (5)

Geometric parameters (Å, º) top

C1—C6	1.375 (6)	C9—O2	1.211 (5)
C1—C2	1.389 (5)	C9—N2	1.348 (5)
C1—N1	1.401 (5)	C10—C11	1.388 (5)
C2—C3	1.377 (6)	C10—C15	1.406 (5)
C2—H2	0.9300	C10—N2	1.408 (5)
C3—C4	1.382 (7)	C11—C12	1.381 (6)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.379 (7)	C12—C13	1.370 (6)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.370 (6)	C13—C14	1.377 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—O1	1.388 (5)	C14—C15	1.374 (6)
C7—N1	1.278 (5)	C14—H14	0.9300
C7—O1	1.362 (5)	C15—O3	1.366 (4)
C7—S1	1.740 (4)	C16—O3	1.426 (5)
C8—C9	1.514 (6)	C16—H16A	0.9600
C8—S1	1.812 (4)	C16—H16B	0.9600
C8—H8A	0.9700	C16—H16C	0.9600
C8—H8B	0.9700	N2—HN2	0.8600

C6—C1—C2	119.4 (4)	C11—C10—N2	124.6 (3)
C6—C1—N1	109.4 (3)	C15—C10—N2	116.7 (3)
C2—C1—N1	131.2 (4)	C12—C11—C10	120.4 (4)
C3—C2—C1	117.2 (4)	C12—C11—H11	119.8
C3—C2—H2	121.4	C10—C11—H11	119.8
C1—C2—H2	121.4	C13—C12—C11	120.4 (4)
C2—C3—C4	121.8 (4)	C13—C12—H12	119.8
C2—C3—H3	119.1	C11—C12—H12	119.8
C4—C3—H3	119.1	C12—C13—C14	120.0 (4)
C5—C4—C3	121.8 (4)	C12—C13—H13	120.0
C5—C4—H4	119.1	C14—C13—H13	120.0
C3—C4—H4	119.1	C15—C14—C13	120.6 (4)
C6—C5—C4	115.3 (4)	C15—C14—H14	119.7
C6—C5—H5	122.3	C13—C14—H14	119.7
C4—C5—H5	122.3	O3—C15—C14	125.4 (3)
C5—C6—C1	124.5 (4)	O3—C15—C10	114.6 (3)
C5—C6—O1	128.0 (4)	C14—C15—C10	120.0 (4)
C1—C6—O1	107.4 (3)	O3—C16—H16A	109.5
N1—C7—O1	117.4 (3)	O3—C16—H16B	109.5
N1—C7—S1	128.1 (3)	H16A—C16—H16B	109.5
O1—C7—S1	114.5 (3)	O3—C16—H16C	109.5
C9—C8—S1	111.7 (3)	H16A—C16—H16C	109.5
C9—C8—H8A	109.3	H16B—C16—H16C	109.5
S1—C8—H8A	109.3	C7—N1—C1	103.1 (3)
C9—C8—H8B	109.3	C9—N2—C10	127.4 (3)
S1—C8—H8B	109.3	C9—N2—HN2	116.3
H8A—C8—H8B	107.9	C10—N2—HN2	116.3
O2—C9—N2	124.7 (4)	C7—O1—C6	102.7 (3)
O2—C9—C8	120.1 (4)	C15—O3—C16	116.7 (3)
N2—C9—C8	115.2 (3)	C7—S1—C8	98.82 (18)
C11—C10—C15	118.7 (4)

C6—C1—C2—C3	−0.6 (6)	N2—C10—C15—O3	−1.0 (5)
N1—C1—C2—C3	−178.6 (4)	C11—C10—C15—C14	0.2 (5)
C1—C2—C3—C4	0.4 (7)	N2—C10—C15—C14	179.1 (3)
C2—C3—C4—C5	0.1 (7)	O1—C7—N1—C1	1.2 (4)
C3—C4—C5—C6	−0.5 (6)	S1—C7—N1—C1	−177.6 (3)
C4—C5—C6—C1	0.3 (6)	C6—C1—N1—C7	−0.9 (4)
C4—C5—C6—O1	178.3 (4)	C2—C1—N1—C7	177.2 (4)
C2—C1—C6—C5	0.3 (6)	O2—C9—N2—C10	0.9 (7)
N1—C1—C6—C5	178.7 (4)	C8—C9—N2—C10	−178.8 (3)
C2—C1—C6—O1	−178.1 (3)	C11—C10—N2—C9	−10.6 (6)
N1—C1—C6—O1	0.3 (4)	C15—C10—N2—C9	170.5 (4)
S1—C8—C9—O2	−88.1 (5)	N1—C7—O1—C6	−1.1 (4)
S1—C8—C9—N2	91.6 (4)	S1—C7—O1—C6	177.9 (2)
C15—C10—C11—C12	0.5 (6)	C5—C6—O1—C7	−177.9 (4)
N2—C10—C11—C12	−178.3 (4)	C1—C6—O1—C7	0.4 (4)
C10—C11—C12—C13	−1.0 (6)	C14—C15—O3—C16	4.8 (6)
C11—C12—C13—C14	0.7 (7)	C10—C15—O3—C16	−175.1 (4)
C12—C13—C14—C15	0.1 (6)	N1—C7—S1—C8	−0.8 (4)
C13—C14—C15—O3	179.7 (4)	O1—C7—S1—C8	−179.7 (3)
C13—C14—C15—C10	−0.5 (6)	C9—C8—S1—C7	−87.7 (3)
C11—C10—C15—O3	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 benzene ring of the methoxy phenyl group.

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O3	0.86	2.22	2.608 (4)	107
N2—HN2···N1	0.86	2.39	3.075 (4)	136
C8—H8A···N1	0.97	2.48	2.914 (5)	107
C11—H11···O2	0.93	2.28	2.869 (5)	121
C12—H12···O2ⁱ	0.93	2.52	3.378 (6)	153
C13—H13···Cg3ⁱⁱ	0.93	2.89	3.634 (5)	138

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

Summary of selected short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
H5···O3	2.72	1 - x, 1 - y, 1 - z
S1···H2	3.10	x, 1/2 - y, 1/2 + z
C5···C1	3.38	1 - x, -y, 1 - z
H8B···C11	3.06	-x, 1 - y, 1 - z
H12···O2	2.52	-x, 2 - y, 1 - z
O2···H16A	2.74	x, 3/2 - y, 1/2 + z
C10···H13	3.04	-x, -1/2 + y, 1/2 - z
C12···H8A	2.82	x, 1 + y, z

Percentage contributions of interatomic contacts to the Hirshfeld surface of the title compound top

Contact	Percentage contribution
H···H	39.3
H···C/C···H	18.0
O···H/H···O	15.6
S···H/H···S	10.2
C···O/O···C	6.0
C···C	4.5
N···H/H···N	4.1
C···N/N···C	1.4
C···S/S···C	0.6
N···O/O···N	0.1

Acknowledgements

The authors acknowledge the Scientific and Technological Research Application and Research Centre, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.

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