Crystal structure of (2Z,5Z)-3-(4-meth­oxy­phen­yl)-2-[(4-meth­oxy­phenyl)­imino]-5-[(E)-3-(2-nitro­phen­yl)allyl­idene]-1,3-thia­zolidin-4-one

Rachida Rahmani; Ahmed Djafri; Jean-Claude Daran; Ayada Djafri; Abdelkader Chouaih; Fodil Hamzaoui

doi:10.1107/S2056989016000207

. 2016 Jan 13;72(Pt 2):155–157. doi: 10.1107/S2056989016000207

Crystal structure of (2Z,5Z)-3-(4-methoxyphenyl)-2-[(4-methoxyphenyl)imino]-5-[(E)-3-(2-nitrophenyl)allylidene]-1,3-thiazolidin-4-one

Rachida Rahmani ^a, Ahmed Djafri ^a, Jean-Claude Daran ^b, Ayada Djafri ^c, Abdelkader Chouaih ^a,^*, Fodil Hamzaoui ^a

PMCID: PMC4770957 PMID: 26958377

The thiazole ring of the title compound is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°.

Keywords: crystal structure, thiazolidinone, hydrogen bonding, π–π stacking

Abstract

In the title compound, C₂₆H₂₁N₃O₅S, the thiazole ring is nearly planar with a maximum deviation of 0.017 (2) Å, and is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°. In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π interactions link the molecules into a three-dimensional supramolecular architecture. Aromatic π–π stacking is also observed between the parallel nitrobenzene rings of neighbouring molecules, the centroid-to-centroid distance being 3.5872 (15) Å.

Chemical context

Heterocycles containing a thiazole ring are found to exhibit a wide spectrum of biological activities (Gautam et al., 2015 ▸; Asif, 2015 ▸; Abhinit et al., 2009 ▸). The thiazolidinones that are used widely in medication are derived from thiazolidines containing sulfur and nitrogen in a five-membered ring (Meera et al., 2014 ▸; Nowaczyk et al., 2014 ▸; Toubal et al., 2012 ▸). Knowledge of the crystal structures of these compounds is crucial for understanding the related biological phenomena (Singh et al., 1981 ▸; Ameta et al., 2014 ▸; Gouda et al., 2011 ▸). As part of our studies in this area, we herein report the synthesis and crystal structure of the title compound.

Structural commentary

The molecular structure with atomic numbering scheme for the title compound is given in Fig. 1 ▸. The N2—C11 and N2—C12 bond lengths [1.385 (3) and 1.389 (3) Å] are intermediate between the classical C—N single-bond length (1.47 Å) and C=N double-bond length (1.27 Å) (Bhagavan, 2002 ▸), indicating that the thiazole moiety is an effective electron-conjugated substructure. The C—S bond lengths in the thiazol rings [S1—C10 = 1.753 (3) and S1—C12 = 1.777 (2) Å] are consistant with the normal Csp ²—S single bond length of 1.76 Å (Sarkar et al., 1984 ▸). The C16—O4 bond length [1.365 (3) Å] and C22—O5 bond length [1.375 (3) Å] are notably shorter than the normal O—C single bond (1.427 Å) (Rong Wan et al., 2008 ▸), indicating that the p orbital occupied lone pair electrons of the oxygen atom in CH₃O and the π orbital in the benzene ring has p–π conjugation. The shorter bond length of C26—O5 [1.385 (5) Å] might be also caused by the delocalized electron density of the conjugated benzene ring. The C25—O4 [1.431 (3) Å] bond length is normal for a C—O single bond.

The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

The thiazole ring is nearly planar with a maximum deviation of 0.017 (2) Å, and is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°with the C1–C6, C13–C18 and C19–C24 rings, respectively.

Supramolecular features

In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π interactions (Table 1 ▸, Fig. 2 ▸) link the molecules into a three-dimensional supramolecular architecture. π–π stacking is also observed between the nearly parallel benzene rings of neighbouring molecules, the centroid-to-centroid distance being 3.5872 (15) Å.

Table 1. Hydrogen-bond geometry (Å, °).

Cg3 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3ⁱ	1.00 (2)	2.55 (2)	3.197 (3)	122 (1)
C9—H9⋯O2ⁱⁱ	0.97 (2)	2.58 (2)	3.400 (3)	142 (1)
C15—H15⋯O1ⁱⁱⁱ	0.93	2.59	3.286 (3)	132
C3—H3⋯Cg3^iv	0.93	2.80	3.560 (3)	140

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

The crystal packing diagram showing π–π stacking between the nitrobenzene rings of the neighbouring molecules.

Synthesis and crystallization

The synthesis of the title compound was performed according to the scheme in Fig. 3 ▸. To a solution of 3 (0.01 mol) in 10 mL of acetic acid and three equivalents of anhydrous sodium acetate was added 2-nitrophenylcinamaldehyde (0.01 mol). The mixture was heated at reflux with stirring, using CH₂Cl₂ (20 mL) for 4 h. The reaction was monitored by TLC using CH₂Cl₂/CH₃CO₂C₂H₅ (9/1) as solvent system. The separated solid was filtered, washed with cold water and dried to give a yellow solid with a moderate yield 75% and melting point 484 K. Single crystals of the title compound suitable for X-ray diffraction were obtained from an ethanol solution.

Chemical pathway showing the formation of the title compound.

IR (KBr, cm⁻¹): 3423.03, 2951 (C—H), 1712 (C=O), 1640.16 (C=N), 1509.93 (C=C), 1030 (C—N), 741(C—S). ¹H NMR, (CDCl₃, 300 MHz) δ (p.p.m.) J (Hz): 3.81 (s, 3H, OCH₃), 3.85 (s, 3H, OCH₃), 6.71 (dd, 1H, J = 15.0 Hz, J = 11.55 Hz, CH), 6.90 (s, 4H, Ar-H), 7.04 (d, 2H, J = 8.8 Hz, Ar-H), 7.35 (d, 2H, J = 8.8 Hz, Ar-H), 7.43–7.67 (m, 5H, Ar-H), 8.0 (d, 1H, J = 8.72 Hz, Chet=CH). ¹³C NMR, (CDCl₃, 300 MHz) δ (p.p.m.): 55.57 (O—CH₃), 55.65 (O—CH₃), 114.57, 114.85, 122.34, 125.22, 126.37, 127.35, 127.99, 128.50, 129.20, 129.57, 129.60, 131.61, 133.36, 135.79, 141.83, 148.13, 150.72, 157.20 (Chet=C), 159.90 (C=N), 165.87 (C=O).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms in the title compound were placed in calculated positions (C—H = 0.96–1.08 Å) and allowed to ride on their parent atoms with U _iso(H) = 1.5U _eq(C) for methyl H atoms and 1.2U _eq(C) for other H atoms.

Table 2. Experimental details.

Crystal data
Chemical formula	C₂₆H₂₁N₃O₅S
M _r	487.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.2727 (10), 8.6401 (4), 21.3018 (12)
β (°)	105.316 (7)
V (Å³)	2356.1 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.18
Crystal size (mm)	0.25 × 0.21 × 0.12

Data collection
Diffractometer	Nonius Kappa CCD
Absorption correction	ψ scan (North et al., 1968 ▸)
T _min, T _max	0.856, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	26882, 5954, 3690
R _int	0.062
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F ² > 2σ(F ²)], wR(F ²), S	0.064, 0.166, 1.02
No. of reflections	5954
No. of parameters	322
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.34

Open in a new tab

Computer programs: KappaCCD (Nonius, 1998 ▸), DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014/7 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸), and Mercury (Macrae et al., 2006 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016000207/xu5881sup1.cif

e-72-00155-sup1.cif^{(922.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016000207/xu5881Isup2.hkl

e-72-00155-Isup2.hkl^{(326.3KB, hkl)}

CCDC reference: 1402626

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge financial support from the Ministère de l’Enseignement Supérieur et de la Recherche Scientifique (MESRS) via the CNEPRU project.

supplementary crystallographic information

Crystal data

C₂₆H₂₁N₃O₅S	F(000) = 1016
M_r = 487.52	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.2727 (10) Å	Cell parameters from 100 reflections
b = 8.6401 (4) Å	θ = 2–29°
c = 21.3018 (12) Å	µ = 0.18 mm⁻¹
β = 105.316 (7)°	T = 173 K
V = 2356.1 (3) Å³	Prism, yellow
Z = 4	0.25 × 0.21 × 0.12 mm

Open in a new tab

Data collection

Nonius Kappa CCD diffractometer	3690 reflections with I > 2σ(I)
θ/2θ scans	R_int = 0.062
Absorption correction: ψ scan (North et al., 1968)	θ_max = 29.5°, θ_min = 2.9°
T_min = 0.856, T_max = 0.919	h = −17→17
26882 measured reflections	k = −11→11
5954 independent reflections	l = −29→27

Open in a new tab

Refinement

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters not refined
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.0731P)² + 0.7139P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
5954 reflections	Δρ_max = 0.49 e Å⁻³
322 parameters	Δρ_min = −0.34 e Å⁻³

Open in a new tab

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Open in a new tab

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

	x	y	z	U_iso*/U_eq
S1	0.28022 (6)	0.41002 (7)	0.22265 (3)	0.0317 (2)
O3	0.14135 (16)	0.4595 (2)	0.35874 (8)	0.0356 (5)
O4	0.29886 (17)	−0.0889 (2)	0.54702 (9)	0.0448 (5)
O2	0.08864 (16)	1.1504 (2)	0.22010 (8)	0.0389 (5)
N2	0.25988 (18)	0.2956 (2)	0.33219 (9)	0.0294 (5)
O1	−0.00470 (18)	1.3059 (2)	0.14901 (10)	0.0498 (6)
N3	0.37138 (19)	0.1521 (2)	0.28522 (10)	0.0345 (5)
N1	0.05420 (18)	1.1947 (2)	0.16354 (11)	0.0335 (5)
C11	0.1930 (2)	0.4215 (3)	0.32243 (12)	0.0287 (6)
C18	0.3513 (2)	0.2234 (3)	0.44293 (12)	0.0320 (6)
H18	0.3978	0.3040	0.4433	0.038*
C13	0.2708 (2)	0.1963 (3)	0.38783 (11)	0.0283 (6)
C10	0.1968 (2)	0.5044 (3)	0.26177 (12)	0.0295 (6)
C1	0.0854 (2)	1.1147 (3)	0.11192 (11)	0.0277 (6)
C8	0.1515 (2)	0.7251 (3)	0.18670 (12)	0.0326 (6)
H8	0.1950 (14)	0.6898 (12)	0.1613 (8)	0.039*
C19	0.4160 (2)	0.1407 (3)	0.23137 (12)	0.0335 (6)
C17	0.3631 (2)	0.1318 (3)	0.49738 (12)	0.0295 (6)
H17	0.4172	0.1505	0.5344	0.035*
C6	0.1071 (2)	0.9552 (3)	0.11536 (11)	0.0290 (6)
C9	0.1448 (2)	0.6358 (3)	0.24244 (12)	0.0324 (6)
H9	0.0994 (15)	0.6736 (12)	0.2677 (8)	0.039*
O5	0.5431 (2)	0.0888 (3)	0.07390 (10)	0.0618 (7)
C7	0.0979 (2)	0.8569 (3)	0.16964 (12)	0.0304 (6)
H7	0.0486 (15)	0.8903 (10)	0.1956 (8)	0.037*
C12	0.3111 (2)	0.2662 (3)	0.28442 (11)	0.0300 (6)
C16	0.2929 (2)	0.0105 (3)	0.49635 (12)	0.0325 (6)
C2	0.0961 (2)	1.2058 (3)	0.06006 (12)	0.0370 (7)
H2	0.0823	1.3114	0.0597	0.044*
C14	0.2003 (2)	0.0780 (3)	0.38674 (13)	0.0396 (7)
H14	0.1461	0.0606	0.3496	0.047*
C5	0.1365 (2)	0.8925 (3)	0.06228 (12)	0.0363 (6)
H5	0.1494	0.7867	0.0618	0.044*
C3	0.1275 (2)	1.1394 (3)	0.00918 (12)	0.0368 (7)
H3	0.1354	1.1995	−0.0254	0.044*
C4	0.1471 (2)	0.9813 (4)	0.01070 (13)	0.0412 (7)
H4	0.1675	0.9350	−0.0234	0.049*
C25	0.3914 (2)	−0.0808 (3)	0.59982 (12)	0.0404 (7)
H25A	0.4516	−0.0953	0.5835	0.061*
H25B	0.3894	−0.1603	0.6310	0.061*
H25C	0.3952	0.0187	0.6204	0.061*
C24	0.3733 (2)	0.0413 (3)	0.18017 (14)	0.0422 (7)
H24	0.3152	−0.0181	0.1807	0.051*
C21	0.5481 (2)	0.2158 (4)	0.17753 (14)	0.0438 (7)
H21	0.6056	0.2763	0.1764	0.053*
C22	0.5053 (3)	0.1118 (3)	0.12736 (13)	0.0414 (7)
C15	0.2106 (2)	−0.0143 (3)	0.44110 (13)	0.0424 (7)
H15	0.1627	−0.0930	0.4408	0.051*
C20	0.5029 (2)	0.2266 (3)	0.22887 (14)	0.0410 (7)
H20	0.5319	0.2939	0.2629	0.049*
C23	0.4174 (3)	0.0305 (3)	0.12806 (13)	0.0457 (8)
H23	0.3865	−0.0331	0.0931	0.055*
C26	0.6246 (3)	0.1806 (5)	0.06639 (18)	0.0720 (12)
H26A	0.6056	0.2876	0.0670	0.108*
H26B	0.6391	0.1571	0.0256	0.108*
H26C	0.6857	0.1606	0.1013	0.108*

Open in a new tab

Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0421 (4)	0.0288 (3)	0.0284 (3)	0.0034 (3)	0.0165 (3)	0.0052 (3)
O3	0.0422 (12)	0.0378 (10)	0.0313 (10)	0.0025 (8)	0.0177 (9)	0.0018 (8)
O4	0.0505 (14)	0.0465 (11)	0.0335 (10)	−0.0113 (10)	0.0043 (10)	0.0158 (9)
O2	0.0459 (13)	0.0443 (10)	0.0261 (10)	−0.0015 (9)	0.0085 (9)	0.0007 (8)
N2	0.0369 (13)	0.0303 (10)	0.0229 (10)	0.0013 (9)	0.0111 (9)	0.0047 (8)
O1	0.0568 (15)	0.0421 (11)	0.0519 (12)	0.0192 (10)	0.0171 (11)	0.0056 (9)
N3	0.0391 (14)	0.0349 (11)	0.0330 (12)	0.0076 (10)	0.0156 (10)	0.0088 (9)
N1	0.0333 (14)	0.0305 (11)	0.0363 (13)	−0.0008 (10)	0.0083 (10)	0.0018 (9)
C11	0.0331 (15)	0.0287 (12)	0.0250 (12)	−0.0039 (11)	0.0094 (11)	−0.0006 (10)
C18	0.0321 (16)	0.0310 (13)	0.0339 (14)	−0.0072 (11)	0.0108 (12)	0.0003 (10)
C13	0.0353 (15)	0.0286 (12)	0.0228 (12)	0.0006 (11)	0.0108 (11)	0.0028 (9)
C10	0.0336 (15)	0.0283 (12)	0.0282 (13)	−0.0023 (11)	0.0113 (11)	−0.0012 (10)
C1	0.0249 (14)	0.0339 (13)	0.0228 (12)	−0.0027 (10)	0.0033 (10)	0.0022 (10)
C8	0.0355 (16)	0.0331 (13)	0.0323 (14)	0.0046 (11)	0.0145 (12)	0.0038 (11)
C19	0.0382 (17)	0.0325 (13)	0.0287 (14)	0.0069 (12)	0.0070 (12)	0.0057 (11)
C17	0.0277 (14)	0.0369 (13)	0.0220 (12)	−0.0031 (11)	0.0029 (10)	0.0009 (10)
C6	0.0246 (14)	0.0360 (13)	0.0262 (13)	0.0024 (11)	0.0066 (11)	0.0043 (10)
C9	0.0350 (16)	0.0328 (13)	0.0320 (14)	0.0012 (11)	0.0136 (12)	0.0034 (11)
O5	0.089 (2)	0.0627 (14)	0.0466 (13)	0.0304 (14)	0.0413 (13)	0.0104 (11)
C7	0.0301 (15)	0.0332 (13)	0.0292 (13)	0.0020 (11)	0.0099 (11)	0.0042 (10)
C12	0.0347 (16)	0.0289 (12)	0.0251 (13)	−0.0029 (11)	0.0057 (11)	0.0043 (10)
C16	0.0380 (16)	0.0322 (13)	0.0267 (13)	−0.0032 (11)	0.0076 (12)	0.0060 (10)
C2	0.0367 (17)	0.0378 (14)	0.0358 (15)	−0.0016 (12)	0.0083 (13)	0.0088 (12)
C14	0.0439 (18)	0.0400 (14)	0.0280 (14)	−0.0110 (13)	−0.0023 (12)	0.0029 (11)
C5	0.0344 (16)	0.0417 (15)	0.0334 (14)	0.0056 (12)	0.0102 (12)	−0.0001 (11)
C3	0.0363 (17)	0.0498 (16)	0.0250 (13)	−0.0067 (13)	0.0095 (12)	0.0083 (12)
C4	0.0393 (18)	0.0611 (18)	0.0259 (14)	0.0010 (14)	0.0134 (12)	−0.0010 (13)
C25	0.0487 (19)	0.0479 (16)	0.0231 (13)	0.0058 (14)	0.0069 (13)	0.0086 (11)
C24	0.0420 (18)	0.0426 (15)	0.0404 (16)	−0.0018 (13)	0.0081 (14)	0.0027 (13)
C21	0.0327 (17)	0.0575 (18)	0.0430 (17)	0.0041 (14)	0.0133 (14)	0.0133 (14)
C22	0.055 (2)	0.0394 (15)	0.0338 (15)	0.0207 (14)	0.0188 (14)	0.0103 (12)
C15	0.0464 (19)	0.0370 (14)	0.0399 (16)	−0.0170 (13)	0.0044 (14)	0.0069 (12)
C20	0.0431 (18)	0.0414 (15)	0.0373 (16)	−0.0006 (13)	0.0086 (14)	−0.0011 (12)
C23	0.059 (2)	0.0449 (16)	0.0297 (15)	−0.0013 (15)	0.0048 (14)	−0.0069 (12)
C26	0.065 (3)	0.100 (3)	0.065 (2)	0.041 (2)	0.042 (2)	0.040 (2)

Open in a new tab

Geometric parameters (Å, º)

S1—C10	1.753 (3)	C9—H9	0.96 (3)
S1—C12	1.777 (2)	O5—C22	1.375 (3)
O3—C11	1.206 (3)	O5—C26	1.385 (5)
O4—C16	1.365 (3)	C7—H7	1.00 (3)
O4—C25	1.431 (3)	C16—C15	1.395 (4)
O2—N1	1.232 (3)	C2—C3	1.384 (4)
N2—C11	1.385 (3)	C2—H2	0.9300
N2—C12	1.389 (3)	C14—C15	1.383 (4)
N2—C13	1.439 (3)	C14—H14	0.9300
O1—N1	1.226 (3)	C5—C4	1.377 (4)
N3—C12	1.267 (3)	C5—H5	0.9300
N3—C19	1.426 (3)	C3—C4	1.389 (4)
N1—C1	1.449 (3)	C3—H3	0.9300
C11—C10	1.490 (3)	C4—H4	0.9300
C18—C17	1.378 (3)	C25—H25A	0.9600
C18—C13	1.383 (4)	C25—H25B	0.9600
C18—H18	0.9300	C25—H25C	0.9600
C13—C14	1.382 (4)	C24—C23	1.388 (4)
C10—C9	1.336 (4)	C24—H24	0.9300
C1—C2	1.394 (3)	C21—C20	1.383 (4)
C1—C6	1.406 (3)	C21—C22	1.397 (4)
C8—C7	1.341 (3)	C21—H21	0.9300
C8—C9	1.438 (3)	C22—C23	1.365 (4)
C8—H8	0.94 (3)	C15—H15	0.9300
C19—C20	1.385 (4)	C20—H20	0.9300
C19—C24	1.386 (4)	C23—H23	0.9300
C17—C16	1.399 (4)	C26—H26A	0.9600
C17—H17	0.9300	C26—H26B	0.9600
C6—C5	1.399 (4)	C26—H26C	0.9600
C6—C7	1.465 (3)

C10—S1—C12	91.41 (12)	O4—C16—C17	124.0 (2)
C16—O4—C25	116.7 (2)	C15—C16—C17	119.9 (2)
C11—N2—C12	116.9 (2)	C3—C2—C1	120.1 (3)
C11—N2—C13	120.9 (2)	C3—C2—H2	120.0
C12—N2—C13	122.1 (2)	C1—C2—H2	120.0
C12—N3—C19	116.0 (2)	C13—C14—C15	119.7 (2)
O1—N1—O2	122.5 (2)	C13—C14—H14	120.1
O1—N1—C1	118.3 (2)	C15—C14—H14	120.1
O2—N1—C1	119.2 (2)	C4—C5—C6	122.5 (3)
O3—C11—N2	124.6 (2)	C4—C5—H5	118.7
O3—C11—C10	125.5 (2)	C6—C5—H5	118.7
N2—C11—C10	109.9 (2)	C2—C3—C4	118.9 (2)
C17—C18—C13	120.5 (2)	C2—C3—H3	120.6
C17—C18—H18	119.7	C4—C3—H3	120.6
C13—C18—H18	119.8	C5—C4—C3	120.6 (3)
C14—C13—C18	120.5 (2)	C5—C4—H4	119.7
C14—C13—N2	120.5 (2)	C3—C4—H4	119.7
C18—C13—N2	119.0 (2)	O4—C25—H25A	109.5
C9—C10—C11	122.8 (2)	O4—C25—H25B	109.5
C9—C10—S1	126.1 (2)	H25A—C25—H25B	109.5
C11—C10—S1	111.07 (18)	O4—C25—H25C	109.5
C2—C1—C6	122.2 (2)	H25A—C25—H25C	109.5
C2—C1—N1	116.2 (2)	H25B—C25—H25C	109.5
C6—C1—N1	121.6 (2)	C19—C24—C23	120.0 (3)
C7—C8—C9	122.4 (3)	C19—C24—H24	120.0
C7—C8—H8	118.8	C23—C24—H24	120.0
C9—C8—H8	118.8	C20—C21—C22	118.3 (3)
C20—C19—C24	118.2 (3)	C20—C21—H21	120.8
C20—C19—N3	121.4 (2)	C22—C21—H21	120.8
C24—C19—N3	120.4 (3)	C23—C22—O5	115.8 (3)
C18—C17—C16	119.3 (2)	C23—C22—C21	119.9 (3)
C18—C17—H17	120.3	O5—C22—C21	124.3 (3)
C16—C17—H17	120.3	C14—C15—C16	120.0 (2)
C5—C6—C1	115.8 (2)	C14—C15—H15	120.0
C5—C6—C7	120.8 (2)	C16—C15—H15	120.0
C1—C6—C7	123.4 (2)	C21—C20—C19	122.3 (3)
C10—C9—C8	124.8 (3)	C21—C20—H20	118.8
C10—C9—H9	117.6	C19—C20—H20	118.8
C8—C9—H9	117.6	C22—C23—C24	121.1 (3)
C22—O5—C26	118.7 (3)	C22—C23—H23	119.5
C8—C7—C6	123.9 (3)	C24—C23—H23	119.5
C8—C7—H7	118.1	O5—C26—H26A	109.5
C6—C7—H7	118.0	O5—C26—H26B	109.5
N3—C12—N2	124.2 (2)	H26A—C26—H26B	109.5
N3—C12—S1	125.1 (2)	O5—C26—H26C	109.5
N2—C12—S1	110.65 (18)	H26A—C26—H26C	109.5
O4—C16—C15	116.1 (2)	H26B—C26—H26C	109.5

C12—N2—C11—O3	178.2 (2)	C11—N2—C12—N3	−177.1 (2)
C13—N2—C11—O3	1.4 (4)	C13—N2—C12—N3	−0.3 (4)
C12—N2—C11—C10	−3.3 (3)	C11—N2—C12—S1	2.9 (3)
C13—N2—C11—C10	179.8 (2)	C13—N2—C12—S1	179.67 (18)
C17—C18—C13—C14	0.7 (4)	C10—S1—C12—N3	178.9 (2)
C17—C18—C13—N2	179.1 (2)	C10—S1—C12—N2	−1.16 (19)
C11—N2—C13—C14	83.3 (3)	C25—O4—C16—C15	170.5 (3)
C12—N2—C13—C14	−93.4 (3)	C25—O4—C16—C17	−9.6 (4)
C11—N2—C13—C18	−95.1 (3)	C18—C17—C16—O4	178.6 (3)
C12—N2—C13—C18	88.2 (3)	C18—C17—C16—C15	−1.5 (4)
O3—C11—C10—C9	2.6 (4)	C6—C1—C2—C3	1.1 (4)
N2—C11—C10—C9	−175.9 (2)	N1—C1—C2—C3	178.8 (2)
O3—C11—C10—S1	−179.3 (2)	C18—C13—C14—C15	−0.3 (4)
N2—C11—C10—S1	2.3 (3)	N2—C13—C14—C15	−178.7 (3)
C12—S1—C10—C9	177.4 (3)	C1—C6—C5—C4	2.1 (4)
C12—S1—C10—C11	−0.63 (19)	C7—C6—C5—C4	−179.2 (3)
O1—N1—C1—C2	33.4 (4)	C1—C2—C3—C4	0.4 (4)
O2—N1—C1—C2	−145.6 (2)	C6—C5—C4—C3	−0.7 (5)
O1—N1—C1—C6	−148.8 (2)	C2—C3—C4—C5	−0.7 (4)
O2—N1—C1—C6	32.2 (4)	C20—C19—C24—C23	−0.4 (4)
C12—N3—C19—C20	81.3 (3)	N3—C19—C24—C23	−179.8 (2)
C12—N3—C19—C24	−99.3 (3)	C26—O5—C22—C23	172.6 (3)
C13—C18—C17—C16	0.2 (4)	C26—O5—C22—C21	−4.3 (4)
C2—C1—C6—C5	−2.3 (4)	C20—C21—C22—C23	3.7 (4)
N1—C1—C6—C5	−179.9 (2)	C20—C21—C22—O5	−179.4 (3)
C2—C1—C6—C7	179.1 (2)	C13—C14—C15—C16	−1.0 (5)
N1—C1—C6—C7	1.5 (4)	O4—C16—C15—C14	−178.1 (3)
C11—C10—C9—C8	175.7 (2)	C17—C16—C15—C14	1.9 (5)
S1—C10—C9—C8	−2.1 (4)	C22—C21—C20—C19	−1.4 (4)
C7—C8—C9—C10	−179.6 (3)	C24—C19—C20—C21	−0.3 (4)
C9—C8—C7—C6	176.6 (2)	N3—C19—C20—C21	179.2 (2)
C5—C6—C7—C8	26.7 (4)	O5—C22—C23—C24	178.5 (3)
C1—C6—C7—C8	−154.7 (3)	C21—C22—C23—C24	−4.4 (4)
C19—N3—C12—N2	179.4 (2)	C19—C24—C23—C22	2.7 (4)
C19—N3—C12—S1	−0.6 (4)

Open in a new tab

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3ⁱ	1.00 (2)	2.55 (2)	3.197 (3)	122 (1)
C9—H9···O2ⁱⁱ	0.97 (2)	2.58 (2)	3.400 (3)	142 (1)
C15—H15···O1ⁱⁱⁱ	0.93	2.59	3.286 (3)	132
C3—H3···Cg3^iv	0.93	2.80	3.560 (3)	140

Open in a new tab

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

References

Abhinit, M., Ghodke, M. & Pratima, N. A. (2009). Int. J. Pharm. Pharm. Sci. 1, 47–64.
Ameta, K. L. & Dandia, A. (2014). Green Chemistry: Synthesis of Bioactive Heterocycles. India: Springer.
Asif, M. (2015). Chem. Int. 1, 1–11.
Bhagavan, N. B. (2002). Medical Biochemistry, 4th ed. London: Academic Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Gautam, D. & Chaudhary, R. P. (2015). Spectrochim. Acta Part A, 135, 219–226. [DOI] [PubMed]
Gouda, M. A. & Abu-Hashem, A. A. (2011). Arch. Pharm. Pharm. Med. Chem. 344, 170–177. [DOI] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.
Meera, R., Devi, P., Muthumani, P. & Sundari, K. J. (2014). Int. J. Biol. & Pharm. Res. 5, 843–847.
Nonius (1998). KappaCCD Reference Manual. Nonius BV, Delft, The Netherlands.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
Nowaczyk, A., Kowiel, M., Gzella, A., Fijałkowski, Ł., Horishny, V. & Lesyk, R. (2014). J. Mol. Model. 20, 2366–2374. [DOI] [PMC free article] [PubMed]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Sarkar, P. B. & Sengupta, S. P. (1984). Z. Kristallogr. 168, 19–23.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.
Singh, S. P., Parmar, S. S., Raman, K. & Stenberg, V. I. (1981). Chem. Rev. 81, 175–203.
Toubal, K., Djafri, A., Chouaih, A. & Talbi, A. (2012). Molecules, 17, 3501–3509. [DOI] [PMC free article] [PubMed]
Wan, R., Yin, L.-H., Han, F., Wang, B. & Wang, J.-T. (2008). Acta Cryst. E64, o795. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989016000207/xu5881sup1.cif

e-72-00155-sup1.cif^{(922.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016000207/xu5881Isup2.hkl

e-72-00155-Isup2.hkl^{(326.3KB, hkl)}

CCDC reference: 1402626

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] Abhinit, M., Ghodke, M. & Pratima, N. A. (2009). Int. J. Pharm. Pharm. Sci. 1, 47–64.

[bb2] Ameta, K. L. & Dandia, A. (2014). Green Chemistry: Synthesis of Bioactive Heterocycles. India: Springer.

[bb3] Asif, M. (2015). Chem. Int. 1, 1–11.

[bb4] Bhagavan, N. B. (2002). Medical Biochemistry, 4th ed. London: Academic Press.

[bb5] Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.

[bb6] Gautam, D. & Chaudhary, R. P. (2015). Spectrochim. Acta Part A, 135, 219–226. [DOI] [PubMed]

[bb7] Gouda, M. A. & Abu-Hashem, A. A. (2011). Arch. Pharm. Pharm. Med. Chem. 344, 170–177. [DOI] [PubMed]

[bb8] Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.

[bb9] Meera, R., Devi, P., Muthumani, P. & Sundari, K. J. (2014). Int. J. Biol. & Pharm. Res. 5, 843–847.

[bb10] Nonius (1998). KappaCCD Reference Manual. Nonius BV, Delft, The Netherlands.

[bb11] North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

[bb12] Nowaczyk, A., Kowiel, M., Gzella, A., Fijałkowski, Ł., Horishny, V. & Lesyk, R. (2014). J. Mol. Model. 20, 2366–2374. [DOI] [PMC free article] [PubMed]

[bb13] Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

[bb14] Sarkar, P. B. & Sengupta, S. P. (1984). Z. Kristallogr. 168, 19–23.

[bb15] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb16] Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.

[bb17] Singh, S. P., Parmar, S. S., Raman, K. & Stenberg, V. I. (1981). Chem. Rev. 81, 175–203.

[bb18] Toubal, K., Djafri, A., Chouaih, A. & Talbi, A. (2012). Molecules, 17, 3501–3509. [DOI] [PMC free article] [PubMed]

[bb19] Wan, R., Yin, L.-H., Han, F., Wang, B. & Wang, J.-T. (2008). Acta Cryst. E64, o795. [DOI] [PMC free article] [PubMed]

PERMALINK

Crystal structure of (2Z,5Z)-3-(4-methoxyphenyl)-2-[(4-methoxyphenyl)imino]-5-[(E)-3-(2-nitrophenyl)allylidene]-1,3-thiazolidin-4-one

Rachida Rahmani

Ahmed Djafri

Jean-Claude Daran

Ayada Djafri

Abdelkader Chouaih

Fodil Hamzaoui

Abstract

Chemical context

Structural commentary

Figure 1.