Crystal structures of two (Z)-2-(4-oxo-1,3-thia­zolidin-2-yl­idene)acetamides

Galushchinskiy, A.; Slepukhin, P.; Obydennov, K.

doi:10.1107/S2056989017016061

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ISSN: 2056-9890

Volume 73| Part 12| December 2017| Pages 1850-1854

https://doi.org/10.1107/S2056989017016061

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Crystal structures of two (Z)-2-(4-oxo-1,3-thiazolidin-2-ylidene)acetamides

Aleksei Galushchinskiy,^a Pavel Slepukhin ^b and Konstantin Obydennov ^a ^*

^aUral Federal University, Mira 19 Ekaterinburg 620002, Russian Federation, and ^b22 Sofia Kovalevskaya str., Ekaterinburg, 620990, Russian Federation
^*Correspondence e-mail: k.l.obydennov@urfu.ru

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 1 November 2017; accepted 7 November 2017; online 10 November 2017)

The crystal structures of two (oxothiazolidin-2-ylidene)acetamides, namely (Z)-2-[2-(morpholin-4-yl)-2-oxoethylidene]thiazolidin-4-one, C₉H₁₂N₂O₃S, (I), and (Z)-N-(4-methoxyphenyl)-2-(4-oxothiazolidin-2-ylidene)acetamide, C₁₂H₁₂N₂O₃S, (II), are described and compared with a related structure. The Z conformation was observed for both the compounds. In (I), the morpholin-4-yl ring has a chair conformation and its mean plane is inclined to the thiazolidine ring mean plane by 37.12 (12)°. In (II), the benzene ring is inclined to the mean plane of the thiazolidine ring by 20.34 (14)°. In the crystal of (I), molecules are linked by N—H⋯O hydrogen bonds, forming C(6) chains along the b-axis direction. The edge-to-edge arrangement of the molecules results in short C—H⋯O and C—H⋯S interactions, which consolidate the chain into a ribbon-like structure. In the crystal of (II), two N—H⋯O hydrogen bonds result in the formation of C(8) chains along the b-axis direction and C(6) chains along the c-axis direction. The combination of these interactions leads to the formation of layers parallel to the bc plane, enclosing R₄⁴(28) rings involving four molecules.

Keywords: crystal structure; thiazolidine; thiazolidin-4-one; acetamide; hydrogen bonding.

CCDC references: 1582018; 1582019

1. Chemical context

Thiazolidine derivatives are of great biological importance due to their antidiabetic (Rizos et al., 2016 ) and antibacterial (Har & Solensky, 2017 ) activity. One such compound, namely (Z)-N-(2-chloro-6-methylphenyl)-2-(3-methyl-4-oxo-1,3-thiazolidin-2-ylidene)acetamide (ralitoline), has been found to be effective in a preclinical anticonvulsant evaluation (Löscher & Schmidt, 1994 ). In view of the importance of 2-(4-oxothiazolidin-2-ylidene)acetamides, the title compounds, (I) and (II), were synthesized and we report herein on their crystal structures. To date, the crystal structure of only one such compound, viz. (Z)-2-cyano-2-(4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)-N-phenylacetamide, (III), has been reported (George, 2012 ).

2. Structural commentary

The molecular structures of the title compounds, (I) and (II), are illustrated in Figs. 1 and 2, respectively. Both compounds crystallize in the monoclinic space group P2₁/c. The Z conformation about the C8=C9 bond is observed for both compounds and favours S⋯O contacts of 2.6902 (18) and 2.738 (3) Å in (I) and (II), respectively. The morpholine ring in compound (I) adopts a chair conformation. The twist angle between the thiazolidine (S1/N2/C9–C11) and amide mean planes (O1/N1/C7/C8) is 10.71 (10)° in (I) and 2.36 (14)° in (II). In (II), the benzene ring plane is inclined to the mean plane of the thiazolidine ring by 20.60 (12)°. The bond lengths and angles in both compounds are similar to those observed for compound (III), mentioned above.

Figure 1
The molecular structure of title compound (I)

, with the atom labelling. Displacement ellipsoids at the 50% probability level.

Figure 2
The molecular structure of title compound (II)

, with the atom labelling. Displacement ellipsoids at the 50% probability level.

3. Supramolecular features

In the crystal of (I), molecules are linked by N—H⋯O hydrogen bonds forming C(6) chains running parallel to the a-axis direction (Table 1 and Fig. 3). The dihedral angle between thiazolidine mean planes is 6.12 (7)°. There are three non-classical C2—H2A⋯S1ⁱ, C5—H5B⋯O3ⁱⁱ and C6—H6B⋯O3ⁱⁱⁱ (Table 1) hydrogen bonds present, linking molecules to form ribbons propagating along [100]; Table 1 and Fig. 3.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.79 (3)	2.11 (3)	2.891 (2)	167 (2)
C2—H2A⋯S1ⁱ	0.97	2.86	3.627 (2)	137
C5—H5B⋯O3ⁱⁱ	0.97	2.55	3.503 (3)	167
C6—H6B⋯O3ⁱⁱⁱ	0.97	2.41	3.179 (3)	136
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 3
A packing diagram of compound (I)

. Dashed lines represent hydrogen bonds. [Symmetry codes: (i) −x + 1, y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (ii) x, y − 1, z; (iii) −x + 1, y − $[{3\over 2}]$ , −z + $[{3\over 2}]$ .]

In crystal of (II), both amide moieties participate in the formation of N—H⋯O hydrogen bonds (see Table 2). These two types of N—H⋯O hydrogen bonds give rise to the formation of two independent C(8) and C(6) chains, running parallel to the b- and c-axes, respectively (see Figs. 4 and 5). Here, the dihedral angle between the thiazolidine mean planes in the N1—H1⋯O3ⁱ and N2—H2⋯O2ⁱⁱ motifs is 79.21 (16)°. The combination of these chain motifs generates a two-dimensional network lying parallel to the bc plane. Each molecule acts as both a double donor and a double acceptor of N—H⋯O hydrogen bonds. The molecules of (II) are linked into aggregated R₄⁴(28) tetramers, which serve as the building blocks of the layers (see Fig. 6).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.95 (2)	1.94 (2)	2.883 (4)	170 (2)
N2—H2⋯O2ⁱⁱ	0.93 (3)	1.92 (3)	2.828 (4)	164 (3)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 4
View of the N1—H1⋯O3ⁱ C(8) chain motif along the b-axis of compound (II)

. Dashed lines represent hydrogen bonds. For clarity, only the bridge H atoms are shown. [Symmetry code: (i) −x, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ .]

Figure 5
View of the N2—H2⋯O2ⁱ C(6) chain motif along the c-axis of the compound (II)

. Dashed lines represent hydrogen bonds. For clarity, only the bridge H atoms are shown. [Symmetry code: (i) x, −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ .]

Figure 6
View of the tetrameric hydrogen-bonded aggregate which serves as the building block of the sheets. [Symmetry code: (i) −x, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) x, −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; (iii) −x, −y + 1, −z + 1.]

4. Database survey

A search of the Cambridge Structural Database (Version 5.38; Groom et al., 2016 ) for the 2-methylene-1,3-thiazolidin-4-one substructure gave nine hits. The compound that most closely resembles the title compounds is 2-cyano-2-(4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)-N-phenylacetamide (III) (NEYGUV; George, 2012). Here the amide mean plane [C—C(=O)—N] is inclined to the mean plane of the thiazolidine ring by 5.09 (16)°, compared to 2.36 (14)° in (II). The benzene ring is inclined to the to the mean plane of the thiazolidine ring by 38.10 (15)° compared to 20.34 (14)° in (II). In the crystal of (III), molecules are linked by N—H⋯O hydrogen bonds, forming chains along the [010] direction. It should be noted that no crystal structures of 2-methylene-1,3-thiazolidin-4-one derivatives without a substituent at the N atom in position 3 of the thiazolidine ring were found.

5. Synthesis and crystallization

Thiazolidinones (I) and (II) were prepared from cyanoacetamides (see Fig. 7), by a previously described method (Obydennov et al., 2017 ). Pyridine was added dropwise with stirring to cyanoacetamide (15 mmol) in a round-bottom flask until complete dissolution of the cyanoacetamide. 4-Dimethylaminopyridine (DMAP) (18 mg, 0.15 mmol) for (I), and mercaptoacetic acid (3.2 ml, 46 mmol) for (II), were added and the mixtures were refluxed for 12 h. They were then cooled to room temperature and diluted with a 0.5 N HCl solution (5 ml). The precipitates formed of the 1,3-thiazolidinones, were filtered off. The crude products were additionally purified by refluxing a suspension of the thiazolidine in MeCN, followed by hot filtration. Colourless crystals of compounds (I) and (II) were obtained by slow evaporation of the respective compound in a solution of DMSO.

Figure 7
Reaction scheme for the title compounds.

(Z)-2-[2-(Morpholin-4-yl)-2-oxoethylidene]-1,3-thiazolidin-4-one (I). Yield 1.54 g (45%), white powder, m.p. 503–505 K. ¹H NMR spectrum, δ, p.p.m. (J, Hz): 3.42 (4H, t, 4.8 Hz, CH₂); 3.54 (2H, s, CH₂); 3.57 (4H, t, 4.8 Hz, CH₂); 5.83 (1H, s, CH); 11.25 (1H, s, NH).

(Z)-N-(4-Methoxyphenyl)-2-(4-oxo-1,3-thiazolidin-2-ylidene)acetamide (II). Yield 2.85 g (72%), white powder, m.p. 534–536 K. (Obydennov et al., 2017). Elemental analysis for C₁₂H₁₂N₂O₃S; found, %: C 54.31; H 4.67; N 10.72; calculated, %: C 54.53; H 4.58; N 10.60.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. For both compounds, the hydrogen atoms were included in calculated positions and refined using the riding model: C—H = 0.93–0.97 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other C-bound H atoms. The NH H atoms were located in difference-Fourier maps and freely refined.

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₉H₁₂N₂O₃S	C₁₂H₁₂N₂O₃S
M_r	228.27	264.30
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c
Temperature (K)	295	295
a, b, c (Å)	9.9740 (4), 11.2175 (4), 9.3155 (4)	11.628 (11), 9.057 (6), 11.525 (12)
β (°)	100.389 (4)	101.13 (8)
V (Å³)	1025.16 (7)	1190.8 (18)
Z	4	4
Radiation type	Mo Kα	Cu Kα
μ (mm⁻¹)	0.30	2.46
Crystal size (mm)	0.25 × 0.2 × 0.15	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos	Oxford Diffraction Xcalibur 3
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2013 )	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.924, 1.000	0.742, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5512, 2777, 2161	8436, 2040, 1398
R_int	0.017	0.053
(sin θ/λ)_max (Å⁻¹)	0.723	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.154, 1.01	0.043, 0.105, 1.01
No. of reflections	2777	2040
No. of parameters	151	172
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.24	0.22, −0.33
Computer programs: CrysAlis PRO (Agilent, 2013), CrysAlis CCD and CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ), OLEX (Dolomanov et al., 2009 ) PLATON (Spek, 2009 ) and publCIF (Westrip, 2011 ).

Supporting information

CCDC references: 1582018; 1582019

Crystal structure: contains datablocks Global, II, I. DOI: https://doi.org/10.1107/S2056989017016061/su5403sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989017016061/su5403Isup2.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989017016061/su5403IIsup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013) for (I); CrysAlis CCD (Oxford Diffraction, 2006) for (II). Cell refinement: CrysAlis PRO (Agilent, 2013) for (I); CrysAlis RED (Oxford Diffraction, 2006) for (II). Data reduction: CrysAlis PRO (Agilent, 2013) for (I); CrysAlis RED (Oxford Diffraction, 2006) for (II). For both structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: OLEX (Dolomanov et al., 2009) for (I); SHELXTL (Sheldrick, 2008) for (II). Software used to prepare material for publication: PLATON (Spek, 2009), OLEX (Dolomanov et al., 2009) and publCIF (Westrip, 2010) for (I); SHELXTL (Sheldrick, 2008) for (II).

(Z)-2-[2-(Morpholin-4-yl)-2-oxoethylidene]thiazolidin-4-one (I) top

Crystal data top

C₉H₁₂N₂O₃S	F(000) = 480
M_r = 228.27	D_x = 1.479 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 9.9740 (4) Å	Cell parameters from 1828 reflections
b = 11.2175 (4) Å	θ = 2.8–30.1°
c = 9.3155 (4) Å	µ = 0.30 mm⁻¹
β = 100.389 (4)°	T = 295 K
V = 1025.16 (7) Å³	Prism, colourless
Z = 4	0.25 × 0.2 × 0.15 mm

Data collection top

Agilent Xcalibur Eos diffractometer	2777 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2161 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 15.9555 pixels mm^-1	θ_max = 30.9°, θ_min = 2.8°
ω scans	h = −14→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→15
T_min = 0.924, T_max = 1.000	l = −8→12
5512 measured 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.1P)² + 0.1P] where P = (F_o² + 2F_c²)/3
2777 reflections	(Δ/σ)_max = 0.001
151 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.24 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	0.41099 (5)	0.19996 (4)	0.86944 (5)	0.04126 (18)
O1	0.60365 (15)	0.17462 (13)	0.70341 (18)	0.0530 (4)
O3	0.20314 (15)	0.45139 (14)	1.00948 (17)	0.0587 (4)
O2	1.01954 (17)	0.35357 (18)	0.6141 (3)	0.0846 (6)
N2	0.37439 (16)	0.42790 (15)	0.87892 (17)	0.0385 (3)
N1	0.74687 (16)	0.31439 (15)	0.6416 (2)	0.0475 (4)
C9	0.45545 (16)	0.34471 (15)	0.82632 (17)	0.0331 (3)
C11	0.27952 (17)	0.38781 (17)	0.95594 (19)	0.0385 (4)
C7	0.63595 (18)	0.28193 (17)	0.6972 (2)	0.0394 (4)
C8	0.55522 (18)	0.37426 (17)	0.7520 (2)	0.0393 (4)
H8	0.572 (2)	0.449 (2)	0.737 (2)	0.047*
C2	0.7968 (2)	0.43485 (19)	0.6280 (3)	0.0591 (6)
H2A	0.7513	0.4892	0.6844	0.071*
H2B	0.7764	0.4595	0.5266	0.071*
C10	0.2832 (2)	0.25413 (19)	0.9676 (2)	0.0441 (4)
C6	0.8258 (2)	0.2254 (2)	0.5779 (3)	0.0652 (7)
H6A	0.8106	0.2352	0.4728	0.078*
H6B	0.7957	0.1461	0.5990	0.078*
C3	0.9469 (3)	0.4400 (3)	0.6813 (4)	0.0813 (9)
H3A	0.9797	0.5188	0.6624	0.098*
H3B	0.9652	0.4275	0.7861	0.098*
C5	0.9720 (2)	0.2383 (2)	0.6379 (3)	0.0647 (6)
H5A	0.9876	0.2223	0.7419	0.078*
H5B	1.0231	0.1802	0.5925	0.078*
H10A	0.302 (3)	0.224 (3)	1.070 (3)	0.075 (8)*
H10B	0.195 (4)	0.232 (3)	0.933 (3)	0.089 (10)*
H2	0.377 (3)	0.498 (3)	0.869 (2)	0.060 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0494 (3)	0.0229 (3)	0.0547 (3)	−0.00327 (18)	0.0178 (2)	−0.00108 (17)
O1	0.0573 (8)	0.0254 (7)	0.0828 (10)	−0.0052 (6)	0.0301 (7)	−0.0098 (6)
O3	0.0605 (9)	0.0382 (8)	0.0881 (10)	0.0025 (7)	0.0422 (8)	0.0000 (7)
O2	0.0595 (10)	0.0483 (11)	0.1621 (18)	−0.0058 (8)	0.0631 (11)	−0.0175 (12)
N2	0.0387 (7)	0.0234 (8)	0.0568 (9)	−0.0013 (6)	0.0173 (6)	−0.0008 (6)
N1	0.0405 (8)	0.0293 (9)	0.0774 (11)	−0.0024 (6)	0.0237 (7)	−0.0110 (7)
C9	0.0346 (8)	0.0226 (8)	0.0419 (8)	−0.0024 (6)	0.0067 (6)	−0.0032 (6)
C11	0.0377 (8)	0.0302 (9)	0.0491 (9)	−0.0032 (7)	0.0119 (7)	−0.0002 (7)
C7	0.0377 (8)	0.0290 (9)	0.0531 (10)	−0.0011 (7)	0.0128 (7)	−0.0052 (7)
C8	0.0392 (8)	0.0221 (8)	0.0597 (10)	−0.0015 (7)	0.0171 (7)	−0.0013 (7)
C2	0.0575 (11)	0.0298 (10)	0.1001 (16)	0.0062 (9)	0.0408 (11)	0.0098 (10)
C10	0.0476 (10)	0.0321 (10)	0.0562 (11)	−0.0026 (8)	0.0195 (8)	0.0039 (8)
C6	0.0599 (13)	0.0455 (13)	0.0992 (18)	−0.0064 (11)	0.0386 (12)	−0.0288 (12)
C3	0.0588 (13)	0.0460 (15)	0.151 (3)	−0.0153 (11)	0.0519 (15)	−0.0309 (16)
C5	0.0581 (13)	0.0446 (13)	0.1004 (18)	0.0148 (11)	0.0380 (12)	0.0041 (12)

Geometric parameters (Å, º) top

S1—C9	1.7490 (17)	C7—C8	1.459 (2)
S1—C10	1.803 (2)	C8—H8	0.87 (3)
O1—C7	1.250 (2)	C2—H2A	0.9700
O3—C11	1.214 (2)	C2—H2B	0.9700
O2—C3	1.422 (3)	C2—C3	1.490 (3)
O2—C5	1.408 (3)	C10—H10A	0.99 (3)
N2—C9	1.381 (2)	C10—H10B	0.91 (3)
N2—C11	1.363 (2)	C6—H6A	0.9700
N2—H2	0.79 (3)	C6—H6B	0.9700
N1—C7	1.353 (2)	C6—C5	1.472 (3)
N1—C2	1.454 (3)	C3—H3A	0.9700
N1—C6	1.462 (3)	C3—H3B	0.9700
C9—C8	1.352 (2)	C5—H5A	0.9700
C11—C10	1.503 (3)	C5—H5B	0.9700

C9—S1—C10	92.02 (8)	C3—C2—H2B	109.6
C5—O2—C3	110.09 (19)	S1—C10—H10A	109.8 (18)
C9—N2—H2	127 (2)	S1—C10—H10B	117 (2)
C11—N2—C9	118.05 (16)	C11—C10—S1	108.05 (13)
C11—N2—H2	115 (2)	C11—C10—H10A	114.0 (17)
C7—N1—C2	126.90 (17)	C11—C10—H10B	104 (2)
C7—N1—C6	120.57 (17)	H10A—C10—H10B	105 (3)
C2—N1—C6	112.42 (17)	N1—C6—H6A	109.6
N2—C9—S1	110.91 (12)	N1—C6—H6B	109.6
C8—C9—S1	125.85 (14)	N1—C6—C5	110.34 (19)
C8—C9—N2	123.23 (16)	H6A—C6—H6B	108.1
O3—C11—N2	124.68 (18)	C5—C6—H6A	109.6
O3—C11—C10	124.40 (16)	C5—C6—H6B	109.6
N2—C11—C10	110.91 (16)	O2—C3—C2	112.8 (2)
O1—C7—N1	120.81 (17)	O2—C3—H3A	109.0
O1—C7—C8	120.27 (17)	O2—C3—H3B	109.0
N1—C7—C8	118.92 (17)	C2—C3—H3A	109.0
C9—C8—C7	120.57 (17)	C2—C3—H3B	109.0
C9—C8—H8	119.9 (15)	H3A—C3—H3B	107.8
C7—C8—H8	119.5 (16)	O2—C5—C6	111.7 (2)
N1—C2—H2A	109.6	O2—C5—H5A	109.3
N1—C2—H2B	109.6	O2—C5—H5B	109.3
N1—C2—C3	110.2 (2)	C6—C5—H5A	109.3
H2A—C2—H2B	108.1	C6—C5—H5B	109.3
C3—C2—H2A	109.6	H5A—C5—H5B	107.9

S1—C9—C8—C7	1.1 (3)	C7—N1—C2—C3	133.5 (2)
O1—C7—C8—C9	8.3 (3)	C7—N1—C6—C5	−130.8 (2)
O3—C11—C10—S1	179.35 (16)	C2—N1—C7—O1	−179.8 (2)
N2—C9—C8—C7	−179.01 (15)	C2—N1—C7—C8	−0.6 (3)
N2—C11—C10—S1	−1.38 (19)	C2—N1—C6—C5	52.9 (3)
N1—C7—C8—C9	−170.79 (18)	C10—S1—C9—N2	−2.10 (14)
N1—C2—C3—O2	53.1 (3)	C10—S1—C9—C8	177.80 (17)
N1—C6—C5—O2	−57.3 (3)	C6—N1—C7—O1	4.4 (3)
C9—S1—C10—C11	1.95 (14)	C6—N1—C7—C8	−176.4 (2)
C9—N2—C11—O3	179.09 (17)	C6—N1—C2—C3	−50.5 (3)
C9—N2—C11—C10	−0.2 (2)	C3—O2—C5—C6	59.6 (3)
C11—N2—C9—S1	1.7 (2)	C5—O2—C3—C2	−57.7 (3)
C11—N2—C9—C8	−178.18 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.79 (3)	2.11 (3)	2.891 (2)	167 (2)
C2—H2A···S1ⁱ	0.97	2.86	3.627 (2)	137
C5—H5B···O3ⁱⁱ	0.97	2.55	3.503 (3)	167
C6—H6B···O3ⁱⁱⁱ	0.97	2.41	3.179 (3)	136

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

(Z)-N-(4-Methoxyphenyl)-2-(4-oxothiazolidin-2-ylidene)acetamide (II) top

Crystal data top

C₁₂H₁₂N₂O₃S	F(000) = 552
M_r = 264.30	D_x = 1.474 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3173 reflections
a = 11.628 (11) Å	θ = 3.8–65.3°
b = 9.057 (6) Å	µ = 2.46 mm⁻¹
c = 11.525 (12) Å	T = 295 K
β = 101.13 (8)°	Prism, colourless
V = 1190.8 (18) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur 3 diffractometer	2040 independent reflections
Radiation source: fine-focus sealed tube	1398 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 66.2°, θ_min = 3.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −12→13
T_min = 0.742, T_max = 1.000	k = −9→10
8436 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
2040 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.12936 (5)	0.11898 (8)	−0.00103 (5)	0.0502 (2)
N1	−0.17601 (18)	0.4274 (3)	−0.04195 (17)	0.0492 (5)
O1	−0.46385 (19)	0.6658 (2)	−0.43527 (18)	0.0749 (6)
C1	−0.2477 (2)	0.4870 (3)	−0.1432 (2)	0.0455 (6)
O2	−0.04377 (14)	0.2965 (2)	−0.12198 (14)	0.0547 (5)
N2	0.10328 (18)	0.1413 (3)	0.21526 (18)	0.0512 (6)
C2	−0.3184 (2)	0.6044 (3)	−0.1284 (2)	0.0509 (6)
H2A	−0.3151	0.6431	−0.0531	0.061*
O3	0.24270 (17)	−0.0064 (2)	0.31929 (16)	0.0660 (6)
C3	−0.3939 (2)	0.6656 (3)	−0.2224 (2)	0.0575 (7)
H3A	−0.4420	0.7441	−0.2108	0.069*
C4	−0.3975 (2)	0.6099 (3)	−0.3341 (2)	0.0530 (6)
C5	−0.3311 (2)	0.4883 (3)	−0.3482 (2)	0.0552 (7)
H5A	−0.3376	0.4468	−0.4230	0.066*
C6	−0.2555 (2)	0.4267 (3)	−0.2548 (2)	0.0510 (6)
H6A	−0.2101	0.3455	−0.2663	0.061*
C7	−0.0826 (2)	0.3377 (3)	−0.0346 (2)	0.0450 (6)
C8	−0.0324 (2)	0.2893 (3)	0.0828 (2)	0.0476 (6)
H8A	−0.0631	0.3248	0.1462	0.057*
C9	0.0570 (2)	0.1951 (3)	0.10347 (19)	0.0443 (6)
C10	0.2276 (2)	0.0170 (3)	0.1101 (2)	0.0528 (7)
H10A	0.2212	−0.0879	0.0930	0.063*
H10B	0.3079	0.0473	0.1117	0.063*
C11	0.1943 (2)	0.0481 (3)	0.2273 (2)	0.0512 (6)
C12	−0.5271 (3)	0.7961 (4)	−0.4254 (3)	0.0815 (10)
H12A	−0.5700	0.8240	−0.5019	0.122*
H12B	−0.4736	0.8737	−0.3945	0.122*
H12C	−0.5807	0.7796	−0.3730	0.122*
H1	−0.198 (2)	0.461 (3)	0.029 (2)	0.058 (7)*
H2	0.068 (3)	0.163 (3)	0.279 (2)	0.067 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0518 (3)	0.0662 (4)	0.0356 (3)	−0.0033 (3)	0.0159 (2)	−0.0037 (3)
N1	0.0515 (11)	0.0638 (14)	0.0335 (11)	0.0009 (10)	0.0108 (9)	−0.0024 (10)
O1	0.0742 (13)	0.0805 (15)	0.0637 (13)	0.0219 (11)	−0.0025 (10)	0.0061 (11)
C1	0.0425 (12)	0.0557 (15)	0.0392 (13)	−0.0076 (11)	0.0106 (10)	−0.0008 (11)
O2	0.0519 (9)	0.0796 (13)	0.0353 (9)	0.0040 (9)	0.0151 (8)	0.0008 (9)
N2	0.0537 (12)	0.0693 (15)	0.0338 (11)	0.0037 (11)	0.0167 (9)	0.0020 (10)
C2	0.0518 (13)	0.0555 (16)	0.0470 (14)	−0.0058 (13)	0.0136 (11)	−0.0108 (12)
O3	0.0672 (12)	0.0876 (15)	0.0454 (12)	0.0110 (10)	0.0165 (9)	0.0173 (10)
C3	0.0524 (14)	0.0550 (16)	0.0645 (19)	0.0025 (12)	0.0097 (13)	−0.0084 (13)
C4	0.0478 (13)	0.0605 (16)	0.0496 (15)	−0.0001 (13)	0.0068 (11)	0.0057 (13)
C5	0.0561 (14)	0.0723 (19)	0.0381 (14)	0.0075 (14)	0.0113 (11)	−0.0013 (12)
C6	0.0526 (13)	0.0635 (17)	0.0384 (13)	0.0071 (13)	0.0126 (11)	−0.0016 (12)
C7	0.0431 (12)	0.0559 (15)	0.0384 (14)	−0.0087 (11)	0.0138 (10)	−0.0031 (11)
C8	0.0485 (13)	0.0624 (17)	0.0342 (13)	−0.0058 (12)	0.0141 (10)	−0.0036 (11)
C9	0.0471 (12)	0.0549 (16)	0.0328 (13)	−0.0093 (12)	0.0126 (10)	0.0006 (11)
C10	0.0570 (14)	0.0615 (17)	0.0430 (15)	−0.0022 (13)	0.0179 (11)	−0.0034 (12)
C11	0.0521 (13)	0.0652 (17)	0.0383 (14)	−0.0058 (13)	0.0138 (11)	0.0053 (13)
C12	0.0685 (19)	0.079 (2)	0.094 (3)	0.0220 (18)	0.0093 (17)	0.0164 (19)

Geometric parameters (Å, º) top

S1—C9	1.739 (3)	C3—C4	1.375 (4)
S1—C10	1.798 (3)	C3—H3A	0.9300
N1—C7	1.346 (3)	C4—C5	1.372 (4)
N1—C1	1.405 (3)	C5—C6	1.370 (4)
N1—H1	0.96 (3)	C5—H5A	0.9300
O1—C4	1.365 (3)	C6—H6A	0.9300
O1—C12	1.407 (4)	C7—C8	1.435 (4)
C1—C2	1.375 (4)	C8—C9	1.330 (4)
C1—C6	1.384 (3)	C8—H8A	0.9300
O2—C7	1.238 (3)	C10—C11	1.501 (4)
N2—C11	1.339 (4)	C10—H10A	0.9700
N2—C9	1.385 (3)	C10—H10B	0.9700
N2—H2	0.92 (3)	C12—H12A	0.9600
C2—C3	1.373 (4)	C12—H12B	0.9600
C2—H2A	0.9300	C12—H12C	0.9600
O3—C11	1.206 (3)

C9—S1—C10	92.05 (13)	C1—C6—H6A	120.4
C7—N1—C1	128.8 (2)	O2—C7—N1	123.1 (2)
C7—N1—H1	119.0 (16)	O2—C7—C8	122.0 (2)
C1—N1—H1	112.1 (16)	N1—C7—C8	114.9 (2)
C4—O1—C12	117.4 (2)	C9—C8—C7	121.7 (2)
C2—C1—C6	119.1 (2)	C9—C8—H8A	119.1
C2—C1—N1	117.9 (2)	C7—C8—H8A	119.1
C6—C1—N1	122.8 (2)	C8—C9—N2	122.8 (2)
C11—N2—C9	118.4 (2)	C8—C9—S1	126.60 (19)
C11—N2—H2	121.0 (17)	N2—C9—S1	110.58 (19)
C9—N2—H2	120.5 (18)	C11—C10—S1	107.8 (2)
C3—C2—C1	121.4 (2)	C11—C10—H10A	110.1
C3—C2—H2A	119.3	S1—C10—H10A	110.1
C1—C2—H2A	119.3	C11—C10—H10B	110.1
C2—C3—C4	119.3 (3)	S1—C10—H10B	110.1
C2—C3—H3A	120.3	H10A—C10—H10B	108.5
C4—C3—H3A	120.3	O3—C11—N2	125.1 (2)
O1—C4—C5	115.7 (2)	O3—C11—C10	123.8 (3)
O1—C4—C3	125.0 (3)	N2—C11—C10	111.1 (2)
C5—C4—C3	119.3 (2)	O1—C12—H12A	109.5
C6—C5—C4	121.6 (2)	O1—C12—H12B	109.5
C6—C5—H5A	119.2	H12A—C12—H12B	109.5
C4—C5—H5A	119.2	O1—C12—H12C	109.5
C5—C6—C1	119.1 (3)	H12A—C12—H12C	109.5
C5—C6—H6A	120.4	H12B—C12—H12C	109.5

C7—N1—C1—C2	−163.6 (2)	C1—N1—C7—C8	−176.5 (2)
C7—N1—C1—C6	20.8 (4)	O2—C7—C8—C9	−1.5 (4)
C6—C1—C2—C3	−2.0 (4)	N1—C7—C8—C9	176.9 (2)
N1—C1—C2—C3	−177.8 (2)	C7—C8—C9—N2	−176.8 (2)
C1—C2—C3—C4	−1.0 (4)	C7—C8—C9—S1	1.6 (4)
C12—O1—C4—C5	−175.9 (3)	C11—N2—C9—C8	−179.2 (2)
C12—O1—C4—C3	4.5 (4)	C11—N2—C9—S1	2.2 (3)
C2—C3—C4—O1	−176.4 (2)	C10—S1—C9—C8	179.6 (2)
C2—C3—C4—C5	4.1 (4)	C10—S1—C9—N2	−1.85 (19)
O1—C4—C5—C6	176.1 (2)	C9—S1—C10—C11	1.19 (19)
C3—C4—C5—C6	−4.2 (4)	C9—N2—C11—O3	179.9 (2)
C4—C5—C6—C1	1.2 (4)	C9—N2—C11—C10	−1.2 (3)
C2—C1—C6—C5	1.9 (4)	S1—C10—C11—O3	178.6 (2)
N1—C1—C6—C5	177.4 (2)	S1—C10—C11—N2	−0.2 (3)
C1—N1—C7—O2	1.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.95 (2)	1.94 (2)	2.883 (4)	170 (2)
N2—H2···O2ⁱⁱ	0.93 (3)	1.92 (3)	2.828 (4)	164 (3)

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

Funding information

This work was supported by the Russian Science Foundation (grant No. 16–16-04022).

References

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Volume 73| Part 12| December 2017| Pages 1850-1854

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