organic compounds
(2E)-4-(4-Bromophenyl)-2-{(2Z)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3-phenyl-2,3-dihydro-1,3-thiazole
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C24H20BrN3S, the dihydrothiazole ring is approximately planar, with a maximum deviation of 0.008 (2) Å, and is twisted with respect to the 4-bromophenyl ring, the phenyl ring and methylphenyl ring, making dihedral angles of 47.96 (8), 59.52 (9) and 16.96 (9)°, respectively. In the crystal, weak C—H⋯π interactions link inversion-related molecules into supramolecular dimers.
CCDC reference: 960927
Related literature
For the syntheses of similar thiazolidine compounds, see, for example: Masoudi et al. (2010); Darehkordia et al. (2007) and for the synthesis of a related compound, see: Mohamed et al. (2013). For the range of biological activities of thiazolidine-containing compounds, see: Pandeya et al. (1999); Shiradkar et al. (2007); Gududuru et al. (2004); Taranalli et al. (2009); Kumar et al. (2007); Rao et al. (2002, 2004); Barreca et al. (2001); Solomon et al. (2007); Amin et al. (2008); Shih & Ying (2004).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 960927
10.1107/S1600536813025506/xu5739sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813025506/xu5739Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813025506/xu5739Isup3.cml
The title compound has been prepared according to our reported method (Mohamed et al., 2013). The crude product has been crystallized from ethanol to afford translucent orange blocks suitable for X-ray diffraction (m.p.: 491 – 493 K).
H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95 (aromatic H) and 0.98 Å (methyl H), with Uiso(H) = 1.2Uiso(C) for aromatic H atoms and Uiso(H) = 1.5Uiso(C) for methyl H atoms.
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. View of the title compound with 50% probability ellipsoids. | |
Fig. 2. Packing of the title compound viewed down the a-axis. |
C24H20BrN3S | Z = 2 |
Mr = 462.40 | F(000) = 472 |
Triclinic, P1 | Dx = 1.495 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9622 (5) Å | Cell parameters from 9928 reflections |
b = 11.2672 (7) Å | θ = 2.4–29.1° |
c = 11.6370 (7) Å | µ = 2.12 mm−1 |
α = 96.273 (1)° | T = 150 K |
β = 94.386 (1)° | Block, translucent orange |
γ = 96.302 (1)° | 0.23 × 0.17 × 0.14 mm |
V = 1027.31 (11) Å3 |
Bruker Smart APEX CCD diffractometer | 5310 independent reflections |
Radiation source: fine-focus sealed tube | 4582 reflections with i > 2σ(i) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 29.1°, θmin = 1.8° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −14→15 |
Tmin = 0.60, Tmax = 0.76 | l = −15→15 |
18958 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.097 | W = 1/[Σ2(FO2) + (0.0545P)2 + 0.2353P] WHERE P = (FO2 + 2FC2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
5310 reflections | Δρmax = 0.97 e Å−3 |
264 parameters | Δρmin = −0.52 e Å−3 |
C24H20BrN3S | γ = 96.302 (1)° |
Mr = 462.40 | V = 1027.31 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9622 (5) Å | Mo Kα radiation |
b = 11.2672 (7) Å | µ = 2.12 mm−1 |
c = 11.6370 (7) Å | T = 150 K |
α = 96.273 (1)° | 0.23 × 0.17 × 0.14 mm |
β = 94.386 (1)° |
Bruker Smart APEX CCD diffractometer | 5310 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 4582 reflections with i > 2σ(i) |
Tmin = 0.60, Tmax = 0.76 | Rint = 0.033 |
18958 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.97 e Å−3 |
5310 reflections | Δρmin = −0.52 e Å−3 |
264 parameters |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at ϕ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in ϕ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.30655 (3) | 0.39026 (2) | 0.30405 (2) | 0.0337 (1) | |
S1 | 0.89651 (6) | −0.07711 (4) | 0.65607 (4) | 0.0232 (1) | |
N1 | 0.91033 (19) | 0.15300 (13) | 0.65666 (13) | 0.0202 (4) | |
N2 | 1.0854 (2) | 0.09850 (14) | 0.80890 (14) | 0.0249 (5) | |
N3 | 1.1384 (2) | −0.00294 (14) | 0.85333 (14) | 0.0232 (4) | |
C1 | 0.7740 (2) | −0.01832 (17) | 0.55032 (17) | 0.0236 (5) | |
C2 | 0.7931 (2) | 0.10264 (17) | 0.56284 (15) | 0.0201 (5) | |
C3 | 0.9789 (2) | 0.06878 (16) | 0.71838 (16) | 0.0209 (5) | |
C4 | 0.6892 (2) | 0.17839 (16) | 0.49902 (16) | 0.0206 (5) | |
C5 | 0.6570 (2) | 0.15626 (18) | 0.37854 (17) | 0.0235 (5) | |
C6 | 0.5459 (2) | 0.22100 (18) | 0.31982 (17) | 0.0249 (5) | |
C7 | 0.4664 (2) | 0.30698 (17) | 0.38211 (17) | 0.0231 (5) | |
C8 | 0.4987 (2) | 0.33198 (17) | 0.50162 (17) | 0.0253 (5) | |
C9 | 0.6109 (2) | 0.26850 (17) | 0.55927 (16) | 0.0227 (5) | |
C10 | 0.9755 (2) | 0.27811 (16) | 0.67949 (16) | 0.0201 (5) | |
C11 | 1.0510 (2) | 0.33501 (17) | 0.59380 (17) | 0.0235 (5) | |
C12 | 1.1144 (3) | 0.45611 (18) | 0.61650 (19) | 0.0284 (6) | |
C13 | 1.1018 (3) | 0.51860 (18) | 0.7235 (2) | 0.0306 (6) | |
C14 | 1.0260 (3) | 0.46116 (19) | 0.80881 (19) | 0.0300 (6) | |
C15 | 0.9628 (2) | 0.34014 (18) | 0.78762 (17) | 0.0248 (5) | |
C16 | 1.2045 (2) | 0.01738 (17) | 0.95964 (16) | 0.0212 (5) | |
C17 | 1.2183 (3) | 0.13675 (18) | 1.03341 (17) | 0.0272 (6) | |
C18 | 1.2755 (2) | −0.08429 (17) | 1.00904 (16) | 0.0217 (5) | |
C19 | 1.3742 (2) | −0.06595 (18) | 1.11581 (17) | 0.0257 (5) | |
C20 | 1.4562 (3) | −0.15780 (19) | 1.15694 (18) | 0.0287 (6) | |
C21 | 1.4419 (3) | −0.27080 (19) | 1.09447 (18) | 0.0283 (6) | |
C22 | 1.3378 (3) | −0.29089 (19) | 0.99012 (19) | 0.0287 (6) | |
C23 | 1.2561 (2) | −0.19953 (18) | 0.94795 (17) | 0.0258 (5) | |
C24 | 1.5419 (3) | −0.3684 (2) | 1.1368 (2) | 0.0354 (7) | |
H1 | 0.70160 | −0.06660 | 0.49030 | 0.0280* | |
H5 | 0.71130 | 0.09670 | 0.33630 | 0.0280* | |
H6 | 0.52480 | 0.20630 | 0.23770 | 0.0300* | |
H8 | 0.44450 | 0.39190 | 0.54330 | 0.0300* | |
H9 | 0.63510 | 0.28630 | 0.64090 | 0.0270* | |
H11 | 1.05960 | 0.29180 | 0.52010 | 0.0280* | |
H12 | 1.16650 | 0.49580 | 0.55810 | 0.0340* | |
H13 | 1.14520 | 0.60130 | 0.73870 | 0.0370* | |
H14 | 1.01710 | 0.50470 | 0.88230 | 0.0360* | |
H15 | 0.91170 | 0.30040 | 0.84640 | 0.0300* | |
H17A | 1.33760 | 0.17120 | 1.04670 | 0.0410* | |
H17B | 1.17330 | 0.12550 | 1.10810 | 0.0410* | |
H17C | 1.15300 | 0.19140 | 0.99360 | 0.0410* | |
H19 | 1.38520 | 0.01050 | 1.16090 | 0.0310* | |
H20 | 1.52320 | −0.14270 | 1.22930 | 0.0340* | |
H22 | 1.32270 | −0.36860 | 0.94720 | 0.0340* | |
H23 | 1.18630 | −0.21560 | 0.87680 | 0.0310* | |
H24A | 1.59110 | −0.34280 | 1.21660 | 0.0530* | |
H24B | 1.63290 | −0.38160 | 1.08640 | 0.0530* | |
H24C | 1.46580 | −0.44330 | 1.13440 | 0.0530* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0380 (1) | 0.0275 (1) | 0.0349 (1) | 0.0071 (1) | −0.0114 (1) | 0.0072 (1) |
S1 | 0.0258 (2) | 0.0195 (2) | 0.0240 (2) | 0.0029 (2) | 0.0006 (2) | 0.0024 (2) |
N1 | 0.0203 (7) | 0.0190 (7) | 0.0203 (8) | 0.0009 (6) | −0.0019 (6) | 0.0022 (6) |
N2 | 0.0260 (8) | 0.0240 (8) | 0.0239 (8) | 0.0026 (6) | −0.0043 (6) | 0.0046 (6) |
N3 | 0.0222 (7) | 0.0247 (8) | 0.0229 (8) | 0.0025 (6) | −0.0008 (6) | 0.0054 (6) |
C1 | 0.0238 (9) | 0.0248 (9) | 0.0209 (9) | 0.0015 (7) | −0.0013 (7) | 0.0008 (7) |
C2 | 0.0186 (8) | 0.0252 (9) | 0.0157 (8) | 0.0015 (7) | 0.0008 (6) | 0.0009 (6) |
C3 | 0.0212 (8) | 0.0213 (8) | 0.0202 (9) | 0.0020 (7) | 0.0017 (7) | 0.0033 (7) |
C4 | 0.0173 (8) | 0.0223 (9) | 0.0210 (9) | −0.0001 (7) | −0.0010 (7) | 0.0018 (7) |
C5 | 0.0213 (8) | 0.0277 (9) | 0.0204 (9) | 0.0025 (7) | 0.0011 (7) | −0.0013 (7) |
C6 | 0.0253 (9) | 0.0310 (10) | 0.0167 (9) | −0.0004 (8) | −0.0020 (7) | 0.0019 (7) |
C7 | 0.0215 (8) | 0.0222 (9) | 0.0247 (9) | 0.0003 (7) | −0.0051 (7) | 0.0057 (7) |
C8 | 0.0255 (9) | 0.0243 (9) | 0.0255 (10) | 0.0042 (7) | 0.0005 (7) | 0.0009 (7) |
C9 | 0.0241 (9) | 0.0245 (9) | 0.0185 (9) | 0.0025 (7) | −0.0001 (7) | 0.0003 (7) |
C10 | 0.0165 (8) | 0.0200 (8) | 0.0230 (9) | 0.0024 (6) | −0.0017 (6) | 0.0017 (7) |
C11 | 0.0231 (9) | 0.0254 (9) | 0.0220 (9) | 0.0044 (7) | 0.0013 (7) | 0.0021 (7) |
C12 | 0.0256 (9) | 0.0276 (10) | 0.0330 (11) | 0.0027 (8) | 0.0007 (8) | 0.0096 (8) |
C13 | 0.0284 (10) | 0.0216 (9) | 0.0397 (12) | 0.0020 (8) | −0.0064 (9) | 0.0014 (8) |
C14 | 0.0297 (10) | 0.0301 (10) | 0.0274 (11) | 0.0055 (8) | −0.0030 (8) | −0.0067 (8) |
C15 | 0.0224 (9) | 0.0293 (10) | 0.0225 (9) | 0.0045 (7) | 0.0004 (7) | 0.0022 (7) |
C16 | 0.0187 (8) | 0.0244 (9) | 0.0203 (9) | 0.0004 (7) | 0.0018 (7) | 0.0036 (7) |
C17 | 0.0327 (10) | 0.0271 (10) | 0.0213 (10) | 0.0022 (8) | −0.0002 (8) | 0.0033 (7) |
C18 | 0.0184 (8) | 0.0283 (9) | 0.0192 (9) | 0.0021 (7) | 0.0030 (7) | 0.0058 (7) |
C19 | 0.0257 (9) | 0.0293 (10) | 0.0211 (9) | −0.0001 (7) | 0.0000 (7) | 0.0040 (7) |
C20 | 0.0258 (9) | 0.0373 (11) | 0.0231 (10) | 0.0008 (8) | −0.0007 (7) | 0.0092 (8) |
C21 | 0.0254 (9) | 0.0347 (11) | 0.0278 (11) | 0.0058 (8) | 0.0056 (8) | 0.0126 (8) |
C22 | 0.0305 (10) | 0.0272 (10) | 0.0292 (11) | 0.0059 (8) | 0.0032 (8) | 0.0041 (8) |
C23 | 0.0254 (9) | 0.0298 (10) | 0.0220 (9) | 0.0027 (8) | 0.0004 (7) | 0.0035 (7) |
C24 | 0.0367 (11) | 0.0373 (12) | 0.0357 (12) | 0.0131 (9) | 0.0028 (9) | 0.0114 (9) |
Br1—C7 | 1.8966 (18) | C18—C23 | 1.397 (3) |
S1—C1 | 1.7439 (19) | C19—C20 | 1.391 (3) |
S1—C3 | 1.7573 (19) | C20—C21 | 1.384 (3) |
N1—C2 | 1.406 (2) | C21—C22 | 1.399 (3) |
N1—C3 | 1.385 (2) | C21—C24 | 1.529 (3) |
N1—C10 | 1.437 (2) | C22—C23 | 1.390 (3) |
N2—N3 | 1.398 (2) | C1—H1 | 0.9500 |
N2—C3 | 1.290 (2) | C5—H5 | 0.9500 |
N3—C16 | 1.293 (2) | C6—H6 | 0.9500 |
C1—C2 | 1.345 (3) | C8—H8 | 0.9500 |
C2—C4 | 1.471 (2) | C9—H9 | 0.9500 |
C4—C5 | 1.396 (3) | C11—H11 | 0.9500 |
C4—C9 | 1.401 (3) | C12—H12 | 0.9500 |
C5—C6 | 1.393 (3) | C13—H13 | 0.9500 |
C6—C7 | 1.384 (3) | C14—H14 | 0.9500 |
C7—C8 | 1.387 (3) | C15—H15 | 0.9500 |
C8—C9 | 1.383 (3) | C17—H17A | 0.9800 |
C10—C11 | 1.383 (3) | C17—H17B | 0.9800 |
C10—C15 | 1.387 (3) | C17—H17C | 0.9800 |
C11—C12 | 1.391 (3) | C19—H19 | 0.9500 |
C12—C13 | 1.378 (3) | C20—H20 | 0.9500 |
C13—C14 | 1.384 (3) | C22—H22 | 0.9500 |
C14—C15 | 1.389 (3) | C23—H23 | 0.9500 |
C16—C17 | 1.503 (3) | C24—H24A | 0.9800 |
C16—C18 | 1.483 (3) | C24—H24B | 0.9800 |
C18—C19 | 1.401 (3) | C24—H24C | 0.9800 |
C1—S1—C3 | 90.57 (9) | C21—C22—C23 | 121.4 (2) |
C2—N1—C3 | 113.95 (15) | C18—C23—C22 | 120.76 (18) |
C2—N1—C10 | 124.72 (15) | S1—C1—H1 | 124.00 |
C3—N1—C10 | 120.74 (15) | C2—C1—H1 | 124.00 |
N3—N2—C3 | 111.32 (15) | C4—C5—H5 | 120.00 |
N2—N3—C16 | 114.04 (16) | C6—C5—H5 | 120.00 |
S1—C1—C2 | 112.77 (14) | C5—C6—H6 | 120.00 |
N1—C2—C1 | 112.72 (16) | C7—C6—H6 | 120.00 |
N1—C2—C4 | 121.09 (16) | C7—C8—H8 | 120.00 |
C1—C2—C4 | 125.66 (16) | C9—C8—H8 | 120.00 |
S1—C3—N1 | 109.97 (12) | C4—C9—H9 | 120.00 |
S1—C3—N2 | 127.42 (14) | C8—C9—H9 | 119.00 |
N1—C3—N2 | 122.60 (16) | C10—C11—H11 | 120.00 |
C2—C4—C5 | 120.73 (16) | C12—C11—H11 | 120.00 |
C2—C4—C9 | 120.26 (16) | C11—C12—H12 | 120.00 |
C5—C4—C9 | 118.85 (16) | C13—C12—H12 | 120.00 |
C4—C5—C6 | 120.42 (17) | C12—C13—H13 | 120.00 |
C5—C6—C7 | 119.41 (18) | C14—C13—H13 | 120.00 |
Br1—C7—C6 | 119.81 (14) | C13—C14—H14 | 120.00 |
Br1—C7—C8 | 118.99 (13) | C15—C14—H14 | 120.00 |
C6—C7—C8 | 121.18 (17) | C10—C15—H15 | 120.00 |
C7—C8—C9 | 119.13 (17) | C14—C15—H15 | 120.00 |
C4—C9—C8 | 120.97 (17) | C16—C17—H17A | 109.00 |
N1—C10—C11 | 119.67 (16) | C16—C17—H17B | 109.00 |
N1—C10—C15 | 119.49 (16) | C16—C17—H17C | 109.00 |
C11—C10—C15 | 120.85 (17) | H17A—C17—H17B | 109.00 |
C10—C11—C12 | 119.43 (18) | H17A—C17—H17C | 109.00 |
C11—C12—C13 | 120.2 (2) | H17B—C17—H17C | 109.00 |
C12—C13—C14 | 120.13 (19) | C18—C19—H19 | 119.00 |
C13—C14—C15 | 120.4 (2) | C20—C19—H19 | 119.00 |
C10—C15—C14 | 119.06 (18) | C19—C20—H20 | 119.00 |
N3—C16—C17 | 124.44 (17) | C21—C20—H20 | 119.00 |
N3—C16—C18 | 116.73 (17) | C21—C22—H22 | 119.00 |
C17—C16—C18 | 118.80 (16) | C23—C22—H22 | 119.00 |
C16—C18—C19 | 120.75 (17) | C18—C23—H23 | 120.00 |
C16—C18—C23 | 121.50 (16) | C22—C23—H23 | 120.00 |
C19—C18—C23 | 117.62 (17) | C21—C24—H24A | 109.00 |
C18—C19—C20 | 121.12 (18) | C21—C24—H24B | 109.00 |
C19—C20—C21 | 121.2 (2) | C21—C24—H24C | 109.00 |
C20—C21—C22 | 117.8 (2) | H24A—C24—H24B | 109.00 |
C20—C21—C24 | 120.7 (2) | H24A—C24—H24C | 110.00 |
C22—C21—C24 | 121.52 (19) | H24B—C24—H24C | 109.00 |
C1—S1—C3—N2 | 178.97 (17) | C5—C4—C9—C8 | 2.3 (3) |
C3—S1—C1—C2 | −0.78 (14) | C4—C5—C6—C7 | −0.5 (3) |
C1—S1—C3—N1 | −0.03 (14) | C5—C6—C7—Br1 | −176.96 (14) |
C3—N1—C10—C11 | 116.25 (19) | C5—C6—C7—C8 | 1.7 (3) |
C3—N1—C2—C1 | −1.4 (2) | C6—C7—C8—C9 | −0.8 (3) |
C3—N1—C10—C15 | −63.3 (2) | Br1—C7—C8—C9 | 177.83 (13) |
C10—N1—C3—N2 | 10.2 (3) | C7—C8—C9—C4 | −1.2 (3) |
C10—N1—C2—C4 | −18.1 (2) | N1—C10—C11—C12 | −179.80 (17) |
C10—N1—C3—S1 | −170.78 (13) | C11—C10—C15—C14 | 0.5 (3) |
C2—N1—C3—N2 | −178.25 (16) | C15—C10—C11—C12 | −0.2 (3) |
C3—N1—C2—C4 | 170.66 (15) | N1—C10—C15—C14 | −179.91 (18) |
C2—N1—C10—C15 | 126.02 (18) | C10—C11—C12—C13 | 0.0 (3) |
C10—N1—C2—C1 | 169.77 (16) | C11—C12—C13—C14 | 0.0 (4) |
C2—N1—C10—C11 | −54.4 (2) | C12—C13—C14—C15 | 0.3 (4) |
C2—N1—C3—S1 | 0.81 (18) | C13—C14—C15—C10 | −0.6 (3) |
N3—N2—C3—S1 | 2.6 (2) | N3—C16—C18—C19 | 169.30 (16) |
C3—N2—N3—C16 | −161.26 (16) | N3—C16—C18—C23 | −6.5 (2) |
N3—N2—C3—N1 | −178.52 (15) | C17—C16—C18—C19 | −8.8 (2) |
N2—N3—C16—C17 | 2.6 (3) | C17—C16—C18—C23 | 175.40 (17) |
N2—N3—C16—C18 | −175.39 (14) | C16—C18—C19—C20 | −173.07 (18) |
S1—C1—C2—N1 | 1.38 (19) | C23—C18—C19—C20 | 2.9 (3) |
S1—C1—C2—C4 | −170.28 (14) | C16—C18—C23—C22 | 173.41 (18) |
N1—C2—C4—C5 | 140.44 (17) | C19—C18—C23—C22 | −2.5 (3) |
C1—C2—C4—C9 | 126.8 (2) | C18—C19—C20—C21 | −0.6 (3) |
C1—C2—C4—C5 | −48.6 (3) | C19—C20—C21—C22 | −2.0 (3) |
N1—C2—C4—C9 | −44.2 (2) | C19—C20—C21—C24 | 176.0 (2) |
C2—C4—C9—C8 | −173.15 (16) | C20—C21—C22—C23 | 2.3 (3) |
C2—C4—C5—C6 | 174.01 (17) | C24—C21—C22—C23 | −175.6 (2) |
C9—C4—C5—C6 | −1.4 (3) | C21—C22—C23—C18 | −0.1 (3) |
Cg4 is the centroid of the C18–C23 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17C···N2 | 0.98 | 2.28 | 2.713 (3) | 105 |
C17—H17A···Cg4i | 0.98 | 2.77 | 3.595 (3) | 143 |
Symmetry code: (i) −x+3, −y, −z+2. |
Cg4 is the centroid of the C18–C23 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17A···Cg4i | 0.98 | 2.77 | 3.595 (3) | 143 |
Symmetry code: (i) −x+3, −y, −z+2. |
Acknowledgements
The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.
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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.
The syntheses of a variety of thiazolidine-containing compounds have been reported (Masoudi et al., 2010; Darehkordia et al., 2007). Such compounds have been found to possess a wide range of biological properties such as antimicrobial (Pandeya et al., 1999; Shiradkar et al., 2007), antiproliferative (Gududuru et al., 2004), anti-inflammatory, analgesic, anti-ulcer (Taranalli et al., 2009; Kumar et al., 2007), anti-HIV (Rao et al., 2002; Rao et al., 2004; Barreca et al., 2001), antimalarial (Solomon et al., 2007), anticonvulsant (Amin et al., 2008) and antioxidant (Shih & Ying, 2004) activities. With this in mind and to further our ongoing study on the synthesis of various derivatives of thiazolidine compounds, we herein report the crystal structure of the title compound.
In Fig. 1, the thiazole ring (S1/N1/C1–C3) of the title compound is planar with an r.m.s. deviation of 0.002 Å. The 4-bromophenyl ring (C4–C9) makes a dihedral angle of 47.96 (8)° with the thiazole ring while the phenyl group (C10–C15) attached to the ring nitrogen makes a dihedral angle of 59.52 (9)°. The dihedral angle between the 4-methylphenyl ring (C18–C23) and the thiazole ring are 16.96 (9)°.
In the crystal, the packing consists of ribbons approximately parallel to [101] and assisted by C17—H17A···Cg4 (Cg4 is the centroid of the C18–C23 ring at 3 - x, -y, 2 - z; H17A···Cg = 2.77 Å, C17—H17A···Cg = 143°) interactions (Table 1).