Crystal structure of methyl (Z)-2-[(Z)-3-methyl-2-({(E)-1-[(R*)-4-methyl­cyclo­hex-3-en-1-yl]ethyl­idene}hydrazinyl­idene)-4-oxo­thia­zolidin-5-yl­idene]acetate

Fawzi, M.; Auhmani, A.; Ait Itto, M.Y.; Riahi, A.; Chevreux, S.; Ketatni, E.M.

doi:10.1107/S2056989017014311

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 73| Part 11| November 2017| Pages 1626-1629

https://doi.org/10.1107/S2056989017014311

Open

access

Crystal structure of methyl (Z)-2-[(Z)-3-methyl-2-({(E)-1-[(R*)-4-methylcyclohex-3-en-1-yl]ethylidene}hydrazinylidene)-4-oxothiazolidin-5-ylidene]acetate

Mourad Fawzi,^a Aziz Auhmani,^a ^* Moulay Youssef Ait Itto,^a Abdelkhalek Riahi,^b Sylviane Chevreux ^b and El Mostafa Ketatni ^c

^aLaboratory of Organic Synthesis and Physico-Molecular Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, PO Box 2390, Marrakech 40001, Morocco, ^bInstitute of Molecular Chemistry of Reims, CNRS UMR 7312 Bat. Europol Agro, Moulin of the Housse UFR Sciences, PO Box 1039-51687 Reims Cedex 2, France, and ^cLaboratory of Applied Spectro-Chemistry and the Environment, University Sultan Moulay Slimane, Faculty of Sciences and Technology, PO Box 523, Beni-Mellal, Morocco
^*Correspondence e-mail: a.auhmani@uca.ma

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 2 October 2017; accepted 3 October 2017; online 13 October 2017)

The new title 4-thiazolidinone derivative, C₁₆H₂₁N₃O₃S, was obtained from the cyclization reaction of 4-methyl-3-thiosemicarbazone and dimethyl acetylenedicarboxylate (DMAD). The cyclohexylidene ring has an envelope conformation with the stereogenic centre C atom as the flap. Its mean plane makes a dihedral angle of 56.23 (9)° with the thiazolidine ring mean plane. In the crystal, molecules are linked by C—H⋯O hydrogen bonds forming chains propagating in the [001] direction. Within the chains there are offset π–π interactions between the thiazolidine rings of inversion-related molecules [centroid–centroid distance = 3.703 (1) Å]. The chains are linked by further C—H⋯O hydrogen bonds, forming slabs parallel to the ac plane.

Keywords: crystal structure: hydrazine: thiazolidinone; C—H⋯O hydrogen bonds; offset π–π interactions.

CCDC reference: 1577993

1. Chemical context

It has been reported that thiazolidinones exhibit antibacterial (Mayekar & Mulwad, 2008 ), antifungal (Omar et al. 2010 ), anticonvulsant (Bhat et al., 2008 ), antitubercular (Babaoglu et al., 2003 ), anti-inflammatory (Vigorita et al. 2003 ), antihistaminic (Agrawal et al., 2000 ), cardiovascular (Suzuki et al., 1999 ) and anti-HIV (Rawal et al., 2005 ) activities.

With the aim of preparing new thiazolidinone derivatives, we report herein on the synthesis (Fig. 1) and crystal structure of the title compound 3, from 4-methyl-3-thiosemicarbazone 1. Treatment of 1 with dimethyl acetylenedicarboxylate 2 in boiling ethanol for 1 h, afforded the thiazolidin-4-one 3 in 90% yield. Its structure has also been fully characterized by NMR spectroscopy while its relative stereochemistry was determined based mainly on the synthetic pathway and implied by the X-ray diffraction analysis.

Figure 1
Reaction scheme for the synthesis of title compound 3.

2. Structural commentary

The title compound 3, is built up from an thiazolidinone ring linked to cyclohexylidene-hydrazone and methoxy-oxoethylidene units (Fig. 2). The compound crystallizes in the centrosymmetric space group P $[\overline{1}]$ , and the stereogenic centre at C8 was assigned as having an R configuration. As expected, the thiazolidine ring and all the atoms attached to it (plane A = S1/C4/C5/N1/C6/N2/N3/O1/C3/C14) are roughly coplanar with an r.m.s. deviation of 0.036 Å. Its mean plane makes a dihedral angle of 56.0 (1)° with the mean plane of the cyclohexylidene ring (C8-C13). The methoxycarbonyl group (C1/O2/O3/C2) is also twisted slightly with respect to plane A, their mean planes being inclined to one another by 11.2 (2)°. The six-membered cyclohexylidene ring has an envelope conformation with atom C8 as the flap: puckering parameters are Q = 0.494 (2) Å, θ = 129.8 (2)° and φ = 180.8 (3)°. The C7=N3 and N2=C6 bond lengths are 1.282 (2) and 1.278 (2) Å, respectively, consistent with C=N double bonding. The C6—N2—N3—C7, C4—C3—C2—O3 and C3—C2—O3—C1 torsion angles are 175.5 (2), −172.4 (2) and 172.5 (2)°, respectively.

Figure 2
The molecular structure of the title compound 3, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

3. Supramolecular features

In the crystal, molecules are linked C3—H3⋯O3ⁱ hydrogen bonds, forming chains propagating along [001]; see Table 1 and Fig. 3. Within the chains there are weak offset π–π stacking interactions between inversion-related thiazole rings [see Fig. 3; Cg1⋯Cg1(−x + 1, −y + 1, −z) = 3.703 (1) Å,where Cg1 is the centroid of the S1/N1/C4–C6 ring, interplanar distance = 3.468 (1) Å, slippage = 1.298 Å]. The chains are linked by further C—H⋯O hydrogen bonds, forming slabs lying parallel to the ac plane (Table 1, Figs. 4 and 5).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.95	2.59	3.4133 (19)	146
C1—H1C⋯O1ⁱⁱ	0.98	2.51	3.208 (2)	128
C14—H14A⋯O2ⁱⁱⁱ	0.98	2.45	3.252 (2)	139
C14—H14B⋯O2^iv	0.98	2.48	3.409 (2)	159
C15—H15A⋯O3^iv	0.98	2.55	3.351 (2)	139
Symmetry codes: (i) -x+1, -y+1, -z-1; (ii) x-1, y, z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z.

Figure 3
Partial crystal packing for title compound 3, showing the C3—H3⋯O3ⁱ hydrogen bonds and the offset π–π interactions between inversion-related molecules, forming chains in the [001] direction (dashed lines; only atom H3 has been included).

Figure 4
Packing and hydrogen-bonding interactions of the title compound viewed along the b axis. For clarity, only the H atoms involved in the hydrogen bonds (dashed lines) interactions have been included.

Figure 5
Packing and hydrogen-bonding interactions of the title compound, viewed along the a axis. For clarity, only the H atoms involved in hydrogen bonding (dashed lines) have been included.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.38, last update May 2017; Groom et al., 2016 ) using a thiazolidone substituted by methoxy-oxoethyllidene and methylhydrazone as the main skeleton gave eight hits. The most relevant structures are methyl (2-{[1-(4-hydroxyphenyl)ethylidene]hydrazono}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate (AGOMUG; Mohamed, Mague et al., 2013 ), methyl (2-{[1-(4-methylphenyl)ethylidene]hydrazono}-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate (NIPPAF; Mague et al., 2013 ) and dimethyl 2-[(4-{N-[5-(2-methoxy-2-oxoethylidene)-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]ethanehydrazonoyl}phenyl)amino]but-2-enedioate (RIMDIC; Mohamed, Akkurt et al., 2013 ).

A comparison of the main C—N, N—N, C—S bond lengths in the title compound and the structures extracted from the CSD shows a good correlation. The C=N—N=C torsion angles indicate that in each case the four atoms are nearly planar, viz. 175.5 (2)° in the title compound, 172.1 (2)° in AGOMUG, −178.9 (2) and −165.5 (2)° in NIPPAF and −167.4 (5)° in RIMDIC.

5. Synthesis and crystallization

To a solution of 4-methyl-3-thiosemicarbazone (200 mg, 1.33 mmol) in ethanol (15 ml) was added dimethyl acetylenedicarboxylate (DMAD) (0.24 ml, 1.66 mmol). The mixture was stirred under reflux for 1 h, leading to the corresponding thiazolidinone. After cooling, the mixture was extracted with ethyl acetate (3 × 20 ml). The organic layer was washed with water, dried on anhydrous Na₂SO₄ and then evaporated under reduced pressure. The obtained residue was chromatographed on a silica gel column using hexane as eluent, to give compound 3 (yield 404 mg, 90%). Yellow prismatic crystals were obtained from a petroleum ether solution, by slow evaporation of the solvent at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were placed in calculated positions with C—H = 0.95–1.00 Å, and refined in the riding-model approximation with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₂₁N₃O₃S
M_r	335.42
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	9.0982 (2), 9.9556 (3), 10.5071 (3)
α, β, γ (°)	66.772 (1), 74.572 (1), 77.706 (1)
V (Å³)	836.76 (4)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	1.88
Crystal size (mm)	0.39 × 0.28 × 0.20

Data collection
Diffractometer	D8 Venture CMOS area detector
Absorption correction	Numerical (SADABS; Bruker, 2012 )
T_min, T_max	0.733, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	30681, 3405, 3195
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.06
No. of reflections	3405
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.46
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg & Putz, 2012 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1577993

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2056989017014311/su5396sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017014311/su5396Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989017014311/su5396Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(Z)-2-[(Z)-3-Methyl-2-({(E)-1-[(R*)-4-methylcyclohex-3-en-1-yl]ethylidene}hydrazinylidene)-4-oxothiazolidin-5-ylidene]acetate top

Crystal data top

C₁₆H₂₁N₃O₃S	Z = 2
M_r = 335.42	F(000) = 356
Triclinic, P1	D_x = 1.331 Mg m⁻³
a = 9.0982 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.9556 (3) Å	Cell parameters from 9903 reflections
c = 10.5071 (3) Å	θ = 4.9–74.5°
α = 66.772 (1)°	µ = 1.88 mm⁻¹
β = 74.572 (1)°	T = 100 K
γ = 77.706 (1)°	Prismatic, yellow
V = 836.76 (4) Å³	0.39 × 0.28 × 0.20 mm

Data collection top

D8 Venture CMOS area detector diffractometer	3195 reflections with I > 2σ(I)
Radiation source: microsource	R_int = 0.035
φ and ω scans	θ_max = 74.5°, θ_min = 4.7°
Absorption correction: numerical (SADABS; Bruker, 2012)	h = −11→11
T_min = 0.733, T_max = 0.919	k = −12→12
30681 measured reflections	l = −12→13
3405 independent 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.048P)² + 0.6482P] where P = (F_o² + 2F_c²)/3
3405 reflections	(Δ/σ)_max = 0.016
212 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.46 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
S1	0.40715 (4)	0.68958 (4)	−0.11410 (4)	0.01854 (12)
O1	0.80122 (13)	0.54559 (13)	−0.29654 (13)	0.0255 (3)
O2	0.21903 (13)	0.59108 (14)	−0.22869 (13)	0.0262 (3)
O3	0.31331 (13)	0.45665 (12)	−0.36926 (12)	0.0219 (3)
N1	0.70665 (15)	0.66298 (14)	−0.13721 (14)	0.0192 (3)
N2	0.56362 (16)	0.77397 (15)	0.02334 (15)	0.0222 (3)
N3	0.40773 (15)	0.81672 (15)	0.07586 (15)	0.0215 (3)
C1	0.15960 (19)	0.4245 (2)	−0.3520 (2)	0.0267 (4)
H1A	0.1267	0.3563	−0.2554	0.040*
H1B	0.1594	0.3793	−0.4196	0.040*
H1C	0.0887	0.5160	−0.3692	0.040*
C2	0.32641 (18)	0.53614 (17)	−0.29626 (17)	0.0194 (3)
C3	0.48814 (18)	0.54559 (17)	−0.30630 (17)	0.0205 (3)
H3	0.5657	0.5084	−0.3690	0.025*
C4	0.52821 (17)	0.60574 (17)	−0.22856 (17)	0.0184 (3)
C5	0.69402 (18)	0.59946 (17)	−0.22780 (17)	0.0193 (3)
C6	0.56930 (18)	0.71493 (17)	−0.06627 (17)	0.0189 (3)
C7	0.38679 (18)	0.86854 (17)	0.17420 (17)	0.0201 (3)
C8	0.22330 (18)	0.90988 (17)	0.23980 (17)	0.0200 (3)
H8	0.2202	1.0019	0.2579	0.024*
C9	0.1056 (2)	0.9394 (2)	0.14898 (19)	0.0281 (4)
H9A	0.1337	1.0203	0.0579	0.034*
H9B	0.1069	0.8502	0.1285	0.034*
C10	−0.0542 (2)	0.9808 (2)	0.22322 (18)	0.0263 (4)
H10	−0.1269	1.0467	0.1702	0.032*
C11	−0.0941 (2)	0.92015 (19)	0.3727 (2)	0.0259 (4)
C12	0.01418 (19)	0.83015 (18)	0.45599 (18)	0.0235 (3)
H12A	−0.0295	0.7375	0.5188	0.028*
H12B	0.0236	0.8805	0.5175	0.028*
C13	0.1742 (2)	0.7892 (2)	0.38279 (19)	0.0289 (4)
H13A	0.1778	0.6962	0.3681	0.035*
H13B	0.2474	0.7725	0.4440	0.035*
C14	0.85481 (18)	0.66081 (19)	−0.10627 (19)	0.0243 (4)
H14A	0.9379	0.6357	−0.1775	0.036*
H14B	0.8625	0.5871	−0.0124	0.036*
H14C	0.8633	0.7581	−0.1082	0.036*
C15	0.51144 (19)	0.88538 (19)	0.23429 (18)	0.0239 (3)
H15A	0.5290	0.7966	0.3162	0.036*
H15B	0.4803	0.9709	0.2638	0.036*
H15C	0.6064	0.8996	0.1621	0.036*
C16	−0.2564 (2)	0.9523 (2)	0.4458 (2)	0.0317 (4)
H16A	−0.3170	0.8763	0.4573	0.048*
H16B	−0.3016	1.0488	0.3888	0.048*
H16C	−0.2564	0.9526	0.5390	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01467 (19)	0.0227 (2)	0.0196 (2)	−0.00267 (14)	−0.00178 (14)	−0.00991 (15)
O1	0.0160 (5)	0.0333 (6)	0.0293 (7)	−0.0041 (5)	0.0009 (5)	−0.0163 (5)
O2	0.0173 (6)	0.0360 (7)	0.0308 (7)	−0.0030 (5)	−0.0017 (5)	−0.0198 (5)
O3	0.0184 (5)	0.0264 (6)	0.0251 (6)	−0.0044 (4)	−0.0042 (4)	−0.0130 (5)
N1	0.0152 (6)	0.0218 (6)	0.0207 (7)	−0.0042 (5)	−0.0028 (5)	−0.0073 (5)
N2	0.0195 (7)	0.0258 (7)	0.0221 (7)	−0.0038 (5)	−0.0033 (5)	−0.0097 (6)
N3	0.0195 (7)	0.0250 (7)	0.0217 (7)	−0.0035 (5)	−0.0025 (5)	−0.0110 (6)
C1	0.0207 (8)	0.0324 (9)	0.0324 (10)	−0.0078 (7)	−0.0060 (7)	−0.0144 (8)
C2	0.0196 (8)	0.0206 (7)	0.0179 (8)	−0.0039 (6)	−0.0031 (6)	−0.0063 (6)
C3	0.0170 (7)	0.0240 (8)	0.0206 (8)	−0.0040 (6)	−0.0001 (6)	−0.0097 (6)
C4	0.0149 (7)	0.0197 (7)	0.0185 (8)	−0.0035 (6)	−0.0002 (6)	−0.0060 (6)
C5	0.0167 (7)	0.0206 (7)	0.0191 (8)	−0.0048 (6)	−0.0011 (6)	−0.0057 (6)
C6	0.0172 (7)	0.0190 (7)	0.0187 (8)	−0.0036 (6)	−0.0030 (6)	−0.0045 (6)
C7	0.0228 (8)	0.0196 (7)	0.0182 (8)	−0.0043 (6)	−0.0052 (6)	−0.0055 (6)
C8	0.0224 (8)	0.0216 (7)	0.0184 (8)	−0.0029 (6)	−0.0050 (6)	−0.0092 (6)
C9	0.0258 (9)	0.0407 (10)	0.0236 (9)	0.0015 (7)	−0.0088 (7)	−0.0180 (8)
C10	0.0229 (8)	0.0360 (9)	0.0225 (9)	−0.0026 (7)	−0.0083 (7)	−0.0111 (7)
C11	0.0227 (8)	0.0282 (8)	0.0349 (10)	−0.0060 (7)	−0.0035 (7)	−0.0197 (8)
C12	0.0267 (8)	0.0240 (8)	0.0210 (8)	−0.0058 (6)	−0.0024 (6)	−0.0096 (7)
C13	0.0260 (9)	0.0283 (9)	0.0239 (9)	0.0004 (7)	−0.0038 (7)	−0.0032 (7)
C14	0.0165 (8)	0.0305 (9)	0.0277 (9)	−0.0028 (6)	−0.0062 (6)	−0.0114 (7)
C15	0.0232 (8)	0.0284 (8)	0.0247 (8)	−0.0027 (6)	−0.0074 (7)	−0.0130 (7)
C16	0.0241 (9)	0.0427 (10)	0.0343 (10)	−0.0031 (7)	−0.0046 (7)	−0.0215 (9)

Geometric parameters (Å, º) top

S1—C4	1.7469 (16)	C8—H8	1.0000
S1—C6	1.7736 (16)	C9—C10	1.512 (2)
O1—C5	1.212 (2)	C9—H9A	0.9900
O2—C2	1.211 (2)	C9—H9B	0.9900
O3—C2	1.3403 (19)	C10—C11	1.416 (3)
O3—C1	1.4495 (19)	C10—H10	0.9500
N1—C5	1.372 (2)	C11—C12	1.415 (2)
N1—C6	1.385 (2)	C11—C16	1.504 (2)
N1—C14	1.462 (2)	C12—C13	1.509 (2)
N2—C6	1.278 (2)	C12—H12A	0.9900
N2—N3	1.4174 (19)	C12—H12B	0.9900
N3—C7	1.282 (2)	C13—H13A	0.9900
C1—H1A	0.9800	C13—H13B	0.9900
C1—H1B	0.9800	C14—H14A	0.9800
C1—H1C	0.9800	C14—H14B	0.9800
C2—C3	1.467 (2)	C14—H14C	0.9800
C3—C4	1.340 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.499 (2)	C15—H15C	0.9800
C7—C15	1.503 (2)	C16—H16A	0.9800
C7—C8	1.508 (2)	C16—H16B	0.9800
C8—C9	1.527 (2)	C16—H16C	0.9800
C8—C13	1.532 (2)

C4—S1—C6	90.05 (7)	C10—C9—H9B	109.4
C2—O3—C1	115.77 (13)	C8—C9—H9B	109.4
C5—N1—C6	115.69 (13)	H9A—C9—H9B	108.0
C5—N1—C14	121.75 (13)	C11—C10—C9	119.25 (15)
C6—N1—C14	122.23 (13)	C11—C10—H10	120.4
C6—N2—N3	108.81 (13)	C9—C10—H10	120.4
C7—N3—N2	114.54 (13)	C12—C11—C10	122.07 (16)
O3—C1—H1A	109.5	C12—C11—C16	118.75 (16)
O3—C1—H1B	109.5	C10—C11—C16	119.18 (16)
H1A—C1—H1B	109.5	C11—C12—C13	118.89 (15)
O3—C1—H1C	109.5	C11—C12—H12A	107.6
H1A—C1—H1C	109.5	C13—C12—H12A	107.6
H1B—C1—H1C	109.5	C11—C12—H12B	107.6
O2—C2—O3	124.53 (14)	C13—C12—H12B	107.6
O2—C2—C3	124.24 (15)	H12A—C12—H12B	107.0
O3—C2—C3	111.22 (13)	C12—C13—C8	111.68 (14)
C4—C3—C2	121.12 (14)	C12—C13—H13A	109.3
C4—C3—H3	119.4	C8—C13—H13A	109.3
C2—C3—H3	119.4	C12—C13—H13B	109.3
C3—C4—C5	120.42 (14)	C8—C13—H13B	109.3
C3—C4—S1	127.81 (12)	H13A—C13—H13B	107.9
C5—C4—S1	111.70 (11)	N1—C14—H14A	109.5
O1—C5—N1	124.96 (14)	N1—C14—H14B	109.5
O1—C5—C4	125.02 (15)	H14A—C14—H14B	109.5
N1—C5—C4	110.01 (13)	N1—C14—H14C	109.5
N2—C6—N1	122.47 (14)	H14A—C14—H14C	109.5
N2—C6—S1	125.00 (12)	H14B—C14—H14C	109.5
N1—C6—S1	112.53 (11)	C7—C15—H15A	109.5
N3—C7—C15	125.43 (15)	C7—C15—H15B	109.5
N3—C7—C8	117.47 (14)	H15A—C15—H15B	109.5
C15—C7—C8	117.04 (14)	C7—C15—H15C	109.5
C7—C8—C9	115.06 (13)	H15A—C15—H15C	109.5
C7—C8—C13	109.94 (13)	H15B—C15—H15C	109.5
C9—C8—C13	108.72 (14)	C11—C16—H16A	109.5
C7—C8—H8	107.6	C11—C16—H16B	109.5
C9—C8—H8	107.6	H16A—C16—H16B	109.5
C13—C8—H8	107.6	C11—C16—H16C	109.5
C10—C9—C8	111.08 (14)	H16A—C16—H16C	109.5
C10—C9—H9A	109.4	H16B—C16—H16C	109.5
C8—C9—H9A	109.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.59	3.4133 (19)	146
C1—H1C···O1ⁱⁱ	0.98	2.51	3.208 (2)	128
C14—H14A···O2ⁱⁱⁱ	0.98	2.45	3.252 (2)	139
C14—H14B···O2^iv	0.98	2.48	3.409 (2)	159
C15—H15A···O3^iv	0.98	2.55	3.351 (2)	139

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

Funding information

Funding for this research was provided by: Cadi Ayyad University.

References

Agrawal, V. K., Sachan, S. & Khadikar, P. V. (2000). Acta Pharm. 50, 281–290. CAS
Babaoglu, K., Page, M. A., Jones, V. C., McNeil, M. R., Dong, C., Naismith, J. H. & Lee, R. E. (2003). Bioorg. Med. Chem. Lett. 13, 3227–3230. Web of Science CrossRef PubMed CAS
Bhat, M. A., Siddiqui, N. & Khan, S. A. (2008). Indian J. Heterocycl. Chem. 17, 287–288. CAS
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals
Mague, J. T., Akkurt, M., Mohamed, S. K., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1401–o1402. CSD CrossRef CAS IUCr Journals
Mayekar, S. A. & Mulwad, V. V. (2008). Indian J. Chem. 47, 1438–1442.
Mohamed, S. K., Akkurt, M., Mague, J. T., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1844–o1845. CSD CrossRef IUCr Journals
Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1553–o1554. CSD CrossRef IUCr Journals
Omar, K., Geronikaki, A., Zoumpoulakis, P., Camoutsis, C., Soković, M., Ćirić, A. & Glamočlija, J. (2010). Bioorg. Med. Chem. 18, 426–432. Web of Science CrossRef PubMed CAS
Rawal, R. K., Prabhakar, Y. S., Katti, S. B. & De Clercq, E. (2005). Bioorg. Med. Chem. 13, 6771–6776. Web of Science CrossRef PubMed CAS
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals
Suzuki, Y., Akima, M. & Tamura, K. (1999). Gen. Pharmacol. 32, 57–63. Web of Science CrossRef CAS PubMed
Vigorita, M. G., Ottanà, R., Monforte, F., Maccari, R., Monforte, M. T., Trovato, A., Taviano, M. F., Miceli, N., De Luca, G., Alcaro, S. & Ortuso, F. (2003). Bioorg. Med. Chem. 11, 999–1006. Web of Science CrossRef PubMed CAS
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals

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.