5-[(1,3-Dimethyl-5-oxo-2-sulfanylideneimidazolidin-4-yl­idene)amino]-2-methyl­isoindoline-1,3-dione

Kotha, S.; Gupta, N.K.; Ansari, S.

doi:10.1107/S2414314621003229

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 4| April 2021| x210322

https://doi.org/10.1107/S2414314621003229

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5-[(1,3-Dimethyl-5-oxo-2-sulfanylideneimidazolidin-4-ylidene)amino]-2-methylisoindoline-1,3-dione

Sambasivarao Kotha,^a ^* Naveen Kumar Gupta ^a and Saima Ansari ^a

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India
^*Correspondence e-mail: srk@chem.iitb.ac.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 March 2021; accepted 26 March 2021; online 9 April 2021)

The title N,N-dimethylthiohydantoin containing an N-methylated pthalimide group, C₁₄H₁₂N₄O₃S, arose from an unexpected reaction in a deep eutectic dimethylthiourea–tartaric acid solvent system. The mean planes of the ring systems are twisted at an angle of 73.84 (17)°. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules.

Keywords: crystal structure; deep eutectic mixture; thiohydantoin; pthalamide; dimethyl thiourea.

CCDC reference: 1847293

Structure description

Thiohydantoins are effective in treating various biological disorders (Spicer et al., 2013 ; Wang et al., 2021 ; Huang et al., 2018 ; Manzanaro et al., 2006 ). In an attempt to synthesize 5-amino-substituted hydantoins and thiohydantoins (Kotha et al., 2019 ), we unexpectedly obtained the title imino-substituted thiohydantoin 1.

The ¹H NMR spectrum confirmed the absence of two H atoms (CH—NH grouping) and the ¹³C spectrum showed the downfield shift for the carbon atom of the C—N bond. To establish its structure unambiguously, the crystal structure was determined, which confirmed the presence of the C10=N3 double bond [1.252 (4) Å] (Fig. 1). The remaining geometrical parameters are comparable with those of a 5-aniline-substituted thiohydantoin reported by our group (Kotha et al., 2019; Cambridge Structural Database refcode FOWGOQ).

Figure 1
The molecular structure of 1, showing 50% displacement ellipsoids.

The molecular structure of 1 has an angular shape and the mean planes defined by the C10–C12/N1/N2 imidazole ring and C1–C9/N4 pthalimide ring system subtend a dihedral angle of 73.84 (17)°. The bond angle of the C8—N3—C10 linker , which connects the thiohydantoin ring with the N-phenyl substituent is 120.6 (3)°, some 4° less than the corresponding angle in FOWGOQ (Fig. 2).

Figure 2
The crystal packing of 1, viewed along the a-axis direction.

The N1 and N2 nitrogen atoms in the imidazole ring are protected by methyl groups, which rules out the possibility of classical hydrogen bonding in the packing (Fig. 2), but several weak C—H⋯O links occur (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5C⋯O2ⁱ	0.98	2.60	3.519 (5)	157
C7—H7⋯O3ⁱⁱ	0.95	2.37	3.302 (4)	166
C9—H9⋯O1ⁱⁱⁱ	0.95	2.47	3.319 (4)	149
C14—H14B⋯O2^iv	0.98	2.32	3.272 (5)	164
Symmetry codes: (i) ; (ii) x+1, y, z; (iii) ; (iv) .

Synthesis and crystallization

Initially, a deep eutectic mixture was obtained by mixing dimethylthiourea and L-tartaric acid (DMTU:L–(+)TA) in 70:30 ratio at 80°C. After obtaining the melt, aniline 2 (100 mg, 0.57 mmol) and ethylglyoxalate 3 (0.12 ml, 1.14 mmol) were added and the mixture was stirred at the same temperature for 6 h. After completion of the reaction (TLC monitoring), the product was concentrated and purified by silica-gel column chromatography using petroleum ether and ethyl acetate as the eluent to afford the title compound 1 (Fig. 3). Yellow plates were recrystallized from chloroform solution (Kotha et al., 2019).

Figure 3
Synthesis scheme for 1

Yield 108 mg, 60%, m.p. 268–270°C, R_f = 0.76 (60% EtOAc–petroleum ether),¹H NMR (500 MHz, CDCl₃) δ 7.79 (d, J = 7.5 Hz, 1H), 7.38 (d, J = 2.0 Hz, 1H), 7.20 (dd, J = 8.0, 1.5 Hz, 1H), 3.42 (s, 3H), 3.15 (s, 3H), 3.03 (s, 3H) p.p.m., ¹³C NMR (125 MHz, CDCl3) δ 180.7, 168.3, 168.3, 154.3, 151.9, 141.4, 133.7, 128.3, 125.3, 124.1, 115.3, 29.6, 28.1, 24.2 p.p.m., HRMS (ESI) calculated for C₁₄H₁₂N₄NaO₃S [M + Na] 339.0522, found 339.0526, IR (neat) 3376, 3028, 1767, 1749, 1738, 1712, 1615, 1405, 1383 cm⁻¹.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₄O₃S
M_r	316.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	5.4887 (9), 9.2470 (12), 27.457 (2)
β (°)	94.75 (1)
V (Å³)	1388.7 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.25
Crystal size (mm)	0.31 × 0.27 × 0.22

Data collection
Diffractometer	Rigaku Oxford Diffraction Saturn724+
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 )
T_min, T_max	0.340, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8048, 2343, 1624
R_int	0.105
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.153, 1.04
No. of reflections	2343
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.35
Computer programs: CrysAlis PRO (Rigaku OD, 2015), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1847293

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003229/hb4377sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003229/hb4377Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621003229/hb4377Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-[(1,3-Dimethyl-5-oxo-2-sulfanylideneimidazolidin-4-ylidene)amino]-2-methylisoindoline-1,3-dione top

Crystal data top

C₁₄H₁₂N₄O₃S	F(000) = 656
M_r = 316.34	D_x = 1.513 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.4887 (9) Å	Cell parameters from 2419 reflections
b = 9.2470 (12) Å	θ = 2.3–31.0°
c = 27.457 (2) Å	µ = 0.25 mm⁻¹
β = 94.75 (1)°	T = 150 K
V = 1388.7 (3) Å³	Plate, yellow
Z = 4	0.31 × 0.27 × 0.22 mm

Data collection top

Rigaku Oxford Diffraction Saturn724+ diffractometer	2343 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	1624 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.105
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 2.3°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysalisPro; Rigaku OD, 2015)	k = −9→10
T_min = 0.340, T_max = 1.000	l = −32→32
8048 measured reflections

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0624P)² + 0.3068P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2343 reflections	Δρ_max = 0.38 e Å⁻³
202 parameters	Δρ_min = −0.34 e Å⁻³
0 restraints

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	0.6276 (2)	0.57457 (11)	0.24925 (3)	0.0309 (3)
O3	0.5648 (5)	0.8470 (2)	0.40427 (8)	0.0257 (7)
O2	0.9716 (5)	0.9678 (3)	0.63093 (8)	0.0257 (7)
O1	0.4516 (5)	0.6022 (3)	0.57964 (8)	0.0316 (7)
N4	0.6704 (5)	0.7946 (3)	0.61393 (9)	0.0209 (7)
N2	0.5470 (6)	0.7361 (3)	0.32835 (9)	0.0221 (7)
N1	0.8657 (6)	0.5885 (3)	0.33889 (9)	0.0220 (7)
N3	1.0073 (6)	0.6355 (3)	0.41971 (9)	0.0248 (8)
C4	0.8759 (7)	0.8769 (4)	0.60409 (11)	0.0207 (9)
C3	0.9437 (7)	0.8266 (4)	0.55580 (11)	0.0203 (9)
C2	0.7823 (7)	0.7184 (4)	0.53916 (11)	0.0227 (9)
C10	0.8555 (7)	0.6584 (4)	0.38396 (11)	0.0213 (9)
C1	0.6097 (7)	0.6926 (4)	0.57754 (11)	0.0216 (9)
C12	0.6818 (7)	0.6322 (4)	0.30574 (11)	0.0214 (9)
C11	0.6395 (7)	0.7596 (4)	0.37603 (11)	0.0221 (9)
C8	0.9789 (7)	0.7009 (4)	0.46559 (11)	0.0250 (9)
C5	0.5476 (7)	0.8074 (4)	0.65885 (11)	0.0289 (10)
H5A	0.664931	0.840036	0.685427	0.043*
H5B	0.481137	0.713115	0.667237	0.043*
H5C	0.414137	0.877738	0.654078	0.043*
C7	1.1494 (7)	0.8039 (4)	0.48344 (11)	0.0268 (10)
H7	1.279648	0.829387	0.464394	0.032*
C9	0.7927 (7)	0.6529 (4)	0.49413 (11)	0.0247 (9)
H9	0.680360	0.579570	0.483004	0.030*
C6	1.1326 (7)	0.8698 (4)	0.52850 (11)	0.0238 (9)
H6	1.246289	0.941822	0.540186	0.029*
C14	0.3422 (7)	0.8152 (4)	0.30389 (12)	0.0284 (10)
H14A	0.403902	0.886751	0.281610	0.043*
H14B	0.251819	0.864661	0.328326	0.043*
H14C	0.233247	0.747504	0.285278	0.043*
C13	1.0409 (8)	0.4761 (4)	0.33055 (13)	0.0360 (11)
H13A	1.175975	0.479863	0.356201	0.054*
H13B	1.104667	0.490714	0.298611	0.054*
H13C	0.960755	0.381459	0.331176	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0393 (8)	0.0339 (7)	0.0201 (5)	0.0062 (5)	0.0060 (4)	−0.0072 (4)
O3	0.0335 (18)	0.0206 (15)	0.0247 (12)	0.0004 (12)	0.0136 (12)	−0.0036 (11)
O2	0.0278 (17)	0.0253 (15)	0.0248 (12)	−0.0008 (12)	0.0064 (11)	−0.0070 (11)
O1	0.0362 (19)	0.0289 (16)	0.0305 (13)	−0.0074 (14)	0.0077 (13)	−0.0029 (12)
N4	0.024 (2)	0.0215 (17)	0.0180 (13)	0.0009 (14)	0.0059 (13)	−0.0003 (12)
N2	0.025 (2)	0.0213 (17)	0.0200 (14)	0.0033 (14)	0.0048 (13)	−0.0030 (13)
N1	0.028 (2)	0.0238 (18)	0.0148 (13)	0.0072 (14)	0.0045 (14)	−0.0038 (12)
N3	0.032 (2)	0.0265 (19)	0.0169 (14)	0.0020 (15)	0.0070 (15)	−0.0017 (13)
C4	0.024 (2)	0.017 (2)	0.0221 (17)	0.0047 (16)	0.0056 (17)	−0.0017 (16)
C3	0.026 (2)	0.016 (2)	0.0191 (16)	0.0056 (16)	0.0027 (16)	0.0020 (14)
C2	0.028 (3)	0.022 (2)	0.0189 (16)	0.0036 (17)	0.0056 (16)	0.0011 (15)
C10	0.027 (2)	0.019 (2)	0.0197 (17)	0.0010 (17)	0.0116 (17)	−0.0003 (15)
C1	0.024 (2)	0.023 (2)	0.0182 (16)	0.0041 (18)	0.0024 (16)	0.0017 (15)
C12	0.023 (2)	0.017 (2)	0.0257 (17)	0.0012 (16)	0.0101 (17)	0.0025 (15)
C11	0.026 (2)	0.019 (2)	0.0225 (16)	−0.0058 (16)	0.0115 (16)	−0.0010 (15)
C8	0.037 (3)	0.021 (2)	0.0177 (16)	0.0078 (18)	0.0074 (17)	0.0006 (15)
C5	0.037 (3)	0.032 (2)	0.0193 (16)	0.0032 (19)	0.0157 (17)	−0.0030 (16)
C7	0.035 (3)	0.026 (2)	0.0208 (17)	0.0046 (19)	0.0112 (17)	0.0000 (16)
C9	0.027 (3)	0.024 (2)	0.0228 (17)	0.0017 (17)	0.0048 (17)	0.0029 (15)
C6	0.026 (3)	0.021 (2)	0.0243 (17)	0.0019 (17)	0.0055 (17)	0.0022 (15)
C14	0.031 (3)	0.026 (2)	0.0290 (18)	0.0074 (18)	0.0048 (17)	0.0010 (17)
C13	0.047 (3)	0.032 (2)	0.0284 (18)	0.020 (2)	0.0041 (19)	−0.0047 (18)

Geometric parameters (Å, º) top

S1—C12	1.644 (3)	C2—C1	1.493 (4)
O3—C11	1.215 (4)	C2—C9	1.382 (4)
O2—C4	1.209 (4)	C10—C11	1.512 (5)
O1—C1	1.210 (4)	C8—C7	1.395 (5)
N4—C4	1.405 (5)	C8—C9	1.410 (5)
N4—C1	1.394 (4)	C5—H5A	0.9800
N4—C5	1.459 (4)	C5—H5B	0.9800
N2—C12	1.390 (4)	C5—H5C	0.9800
N2—C11	1.382 (4)	C7—H7	0.9500
N2—C14	1.458 (5)	C7—C6	1.389 (4)
N1—C10	1.401 (4)	C9—H9	0.9500
N1—C12	1.363 (5)	C6—H6	0.9500
N1—C13	1.448 (4)	C14—H14A	0.9800
N3—C10	1.252 (4)	C14—H14B	0.9800
N3—C8	1.417 (4)	C14—H14C	0.9800
C4—C3	1.481 (4)	C13—H13A	0.9800
C3—C2	1.389 (5)	C13—H13B	0.9800
C3—C6	1.387 (5)	C13—H13C	0.9800

C4—N4—C5	123.6 (3)	C7—C8—N3	118.9 (3)
C1—N4—C4	112.1 (3)	C7—C8—C9	121.0 (3)
C1—N4—C5	124.1 (3)	C9—C8—N3	119.9 (3)
C12—N2—C14	124.0 (3)	N4—C5—H5A	109.5
C11—N2—C12	111.4 (3)	N4—C5—H5B	109.5
C11—N2—C14	124.5 (3)	N4—C5—H5C	109.5
C10—N1—C13	123.1 (3)	H5A—C5—H5B	109.5
C12—N1—C10	111.8 (3)	H5A—C5—H5C	109.5
C12—N1—C13	124.9 (3)	H5B—C5—H5C	109.5
C10—N3—C8	120.6 (3)	C8—C7—H7	119.3
O2—C4—N4	125.1 (3)	C6—C7—C8	121.4 (3)
O2—C4—C3	129.4 (3)	C6—C7—H7	119.3
N4—C4—C3	105.5 (3)	C2—C9—C8	116.4 (3)
C2—C3—C4	108.7 (3)	C2—C9—H9	121.8
C6—C3—C4	130.4 (3)	C8—C9—H9	121.8
C6—C3—C2	121.0 (3)	C3—C6—C7	117.5 (3)
C3—C2—C1	107.9 (3)	C3—C6—H6	121.2
C9—C2—C3	122.5 (3)	C7—C6—H6	121.2
C9—C2—C1	129.6 (3)	N2—C14—H14A	109.5
N1—C10—C11	104.3 (3)	N2—C14—H14B	109.5
N3—C10—N1	122.8 (3)	N2—C14—H14C	109.5
N3—C10—C11	132.9 (3)	H14A—C14—H14B	109.5
O1—C1—N4	124.3 (3)	H14A—C14—H14C	109.5
O1—C1—C2	130.1 (3)	H14B—C14—H14C	109.5
N4—C1—C2	105.7 (3)	N1—C13—H13A	109.5
N2—C12—S1	125.7 (3)	N1—C13—H13B	109.5
N1—C12—S1	126.9 (3)	N1—C13—H13C	109.5
N1—C12—N2	107.4 (3)	H13A—C13—H13B	109.5
O3—C11—N2	126.3 (3)	H13A—C13—H13C	109.5
O3—C11—C10	128.5 (3)	H13B—C13—H13C	109.5
N2—C11—C10	105.1 (3)

O2—C4—C3—C2	179.0 (4)	C12—N2—C11—C10	−0.3 (4)
O2—C4—C3—C6	−0.2 (7)	C12—N1—C10—N3	−179.6 (3)
N4—C4—C3—C2	−0.5 (4)	C12—N1—C10—C11	−1.4 (4)
N4—C4—C3—C6	−179.6 (4)	C11—N2—C12—S1	179.7 (3)
N1—C10—C11—O3	−176.8 (3)	C11—N2—C12—N1	−0.6 (4)
N1—C10—C11—N2	1.0 (3)	C8—N3—C10—N1	−175.4 (3)
N3—C10—C11—O3	1.1 (6)	C8—N3—C10—C11	7.1 (6)
N3—C10—C11—N2	178.9 (4)	C8—C7—C6—C3	1.8 (6)
N3—C8—C7—C6	−179.0 (3)	C5—N4—C4—O2	−1.0 (6)
N3—C8—C9—C2	177.7 (3)	C5—N4—C4—C3	178.5 (3)
C4—N4—C1—O1	174.2 (4)	C5—N4—C1—O1	−1.3 (6)
C4—N4—C1—C2	−4.0 (4)	C5—N4—C1—C2	−179.5 (3)
C4—C3—C2—C1	−1.9 (4)	C7—C8—C9—C2	3.1 (5)
C4—C3—C2—C9	177.7 (3)	C9—C2—C1—O1	5.9 (7)
C4—C3—C6—C7	−179.1 (3)	C9—C2—C1—N4	−175.9 (4)
C3—C2—C1—O1	−174.6 (4)	C9—C8—C7—C6	−4.3 (6)
C3—C2—C1—N4	3.6 (4)	C6—C3—C2—C1	177.4 (3)
C3—C2—C9—C8	0.6 (5)	C6—C3—C2—C9	−3.1 (6)
C2—C3—C6—C7	1.9 (5)	C14—N2—C12—S1	−3.3 (5)
C10—N1—C12—S1	−179.0 (3)	C14—N2—C12—N1	176.4 (3)
C10—N1—C12—N2	1.3 (4)	C14—N2—C11—O3	0.6 (5)
C10—N3—C8—C7	−113.3 (4)	C14—N2—C11—C10	−177.2 (3)
C10—N3—C8—C9	72.0 (5)	C13—N1—C10—N3	4.7 (5)
C1—N4—C4—O2	−176.6 (3)	C13—N1—C10—C11	−177.1 (3)
C1—N4—C4—C3	2.9 (4)	C13—N1—C12—S1	−3.4 (5)
C1—C2—C9—C8	−180.0 (4)	C13—N1—C12—N2	176.9 (3)
C12—N2—C11—O3	177.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5C···O2ⁱ	0.98	2.60	3.519 (5)	157
C7—H7···O3ⁱⁱ	0.95	2.37	3.302 (4)	166
C9—H9···O1ⁱⁱⁱ	0.95	2.47	3.319 (4)	149
C14—H14B···O2^iv	0.98	2.32	3.272 (5)	164

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

Acknowledgements

We thank Darshan S Mhatre for his help in collecting the X-ray data and the structure refinement.

Funding information

Funding for this research was provided by: Department of Science and Technology, Ministry of Science and Technology, India (grant No. SR/S2/JCB33/2010 to Prof. Sambasivarao Kotha); Council of Scientific and Industrial Research, India (scholarship to Naveen Kumar Gupta); University Grants Commission (scholarship to Saima Ansari).

References

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