organic compounds
Methyl 2-((2Z,5Z)-4-oxo-3-phenyl-2-{2-[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]hydrazin-1-ylidene}-1,3-thiazolidin-5-ylidene)acetate
aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C22H19N3O3S, the six-membered ring of the 1,2,3,4-tetrahydronaphthalene ring system adopts an with the central CH2 C atom as the flap. The molecular conformation is stabilized by an S⋯O contact, forming a pseudo-five-membered ring. In the crystal, molecules are linked via C—H⋯O hydrogen bonds into chains propagating along [102].
CCDC reference: 990619
Related literature
For the synthesis of thiazolidinediones, see: Patel et al. (2010); Aneja et al. (2011). For pharmacological properties of thiazolidinedione-containing compounds, see: Gillies & Dunn (2000); Lenhard & Funk (2001); Edelman (2003); Desmet et al. (2005). For ring conformation, see: Cremer & Pople (1975). For the synthesis of the title compound, see: Mague et al. (2014).
Experimental
Crystal data
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Refinement
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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: SHELXL2013 (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: 990619
10.1107/S1600536814005285/bt6966sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005285/bt6966Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814005285/bt6966Isup3.cml
The title compound was synthesized based on our previous reported method (Mague et al., 2014). Orange crystals (m.p.501–503 K) suitable for X-ray analysis were grown from an ethanolic solution at room temperature after two days.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H = 0.95–0.99 Å, with Uiso(H) = 1.2 or 1.5 Uiso(C).
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: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C22H19N3O3S | Z = 2 |
Mr = 405.47 | F(000) = 424 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7078 (6) Å | Cell parameters from 9980 reflections |
b = 9.7134 (6) Å | θ = 2.3–29.2° |
c = 11.1061 (7) Å | µ = 0.20 mm−1 |
α = 67.9810 (9)° | T = 150 K |
β = 88.8400 (9)° | Thick plate, orange |
γ = 85.9840 (9)° | 0.28 × 0.16 × 0.09 mm |
V = 968.47 (10) Å3 |
Bruker SMART APEX CCD diffractometer | 4994 independent reflections |
Radiation source: fine-focus sealed tube | 4325 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 29.2°, θmin = 2.0° |
ϕ and ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −13→13 |
Tmin = 0.83, Tmax = 0.98 | l = −14→15 |
17735 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0495P)2 + 0.3384P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4994 reflections | Δρmax = 0.39 e Å−3 |
263 parameters | Δρmin = −0.30 e Å−3 |
C22H19N3O3S | γ = 85.9840 (9)° |
Mr = 405.47 | V = 968.47 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.7078 (6) Å | Mo Kα radiation |
b = 9.7134 (6) Å | µ = 0.20 mm−1 |
c = 11.1061 (7) Å | T = 150 K |
α = 67.9810 (9)° | 0.28 × 0.16 × 0.09 mm |
β = 88.8400 (9)° |
Bruker SMART APEX CCD diffractometer | 4994 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 4325 reflections with I > 2σ(I) |
Tmin = 0.83, Tmax = 0.98 | Rint = 0.036 |
17735 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.39 e Å−3 |
4994 reflections | Δρmin = −0.30 e Å−3 |
263 parameters |
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 | ||
S1 | 0.52540 (3) | 0.95022 (3) | 0.67094 (3) | 0.0188 (1) | |
O1 | 0.76785 (10) | 0.63932 (11) | 0.62875 (11) | 0.0310 (3) | |
O2 | 0.66788 (9) | 1.19374 (10) | 0.53017 (10) | 0.0249 (3) | |
O3 | 0.88571 (9) | 1.18392 (10) | 0.45791 (10) | 0.0255 (3) | |
N1 | 0.56204 (10) | 0.66168 (12) | 0.72779 (11) | 0.0189 (3) | |
N2 | 0.34944 (11) | 0.73712 (12) | 0.79413 (11) | 0.0200 (3) | |
N3 | 0.27229 (11) | 0.87024 (12) | 0.78071 (11) | 0.0209 (3) | |
C1 | 0.67901 (13) | 0.71539 (14) | 0.65725 (13) | 0.0208 (3) | |
C2 | 0.67731 (12) | 0.88043 (14) | 0.62092 (13) | 0.0192 (3) | |
C3 | 0.46688 (12) | 0.76959 (14) | 0.74001 (12) | 0.0178 (3) | |
C4 | 0.52709 (12) | 0.50951 (14) | 0.76333 (13) | 0.0185 (3) | |
C5 | 0.46558 (14) | 0.47045 (15) | 0.67052 (13) | 0.0237 (3) | |
C6 | 0.42866 (15) | 0.32512 (16) | 0.70419 (15) | 0.0286 (4) | |
C7 | 0.45075 (15) | 0.22246 (15) | 0.82939 (15) | 0.0274 (4) | |
C8 | 0.51370 (15) | 0.26328 (15) | 0.92091 (14) | 0.0267 (4) | |
C9 | 0.55316 (14) | 0.40784 (15) | 0.88794 (13) | 0.0234 (4) | |
C10 | 0.15034 (12) | 0.85321 (14) | 0.83051 (12) | 0.0188 (3) | |
C11 | 0.09413 (14) | 0.70582 (15) | 0.90877 (14) | 0.0251 (4) | |
C12 | −0.06198 (15) | 0.71071 (17) | 0.89171 (16) | 0.0333 (5) | |
C13 | −0.13270 (15) | 0.83434 (19) | 0.92826 (16) | 0.0363 (5) | |
C14 | −0.07537 (14) | 0.98191 (17) | 0.85397 (14) | 0.0271 (4) | |
C15 | −0.15709 (16) | 1.1146 (2) | 0.82824 (16) | 0.0369 (5) | |
C16 | −0.10746 (18) | 1.25107 (19) | 0.75859 (17) | 0.0400 (5) | |
C17 | 0.02647 (18) | 1.25928 (18) | 0.71144 (17) | 0.0379 (5) | |
C18 | 0.10916 (15) | 1.12992 (16) | 0.73521 (15) | 0.0289 (4) | |
C19 | 0.06062 (13) | 0.99048 (15) | 0.80716 (13) | 0.0216 (3) | |
C20 | 0.78083 (13) | 0.96017 (14) | 0.55569 (13) | 0.0219 (4) | |
C21 | 0.77041 (13) | 1.12321 (14) | 0.51469 (13) | 0.0210 (3) | |
C22 | 0.88037 (15) | 1.34487 (15) | 0.40941 (15) | 0.0282 (4) | |
H5 | 0.44880 | 0.54180 | 0.58520 | 0.0280* | |
H6 | 0.38810 | 0.29610 | 0.64100 | 0.0340* | |
H7 | 0.42280 | 0.12400 | 0.85270 | 0.0330* | |
H8 | 0.52990 | 0.19220 | 1.00640 | 0.0320* | |
H9 | 0.59720 | 0.43610 | 0.94990 | 0.0280* | |
H11A | 0.11620 | 0.67920 | 1.00170 | 0.0300* | |
H11B | 0.13900 | 0.62790 | 0.88110 | 0.0300* | |
H12A | −0.08400 | 0.72830 | 0.80030 | 0.0400* | |
H12B | −0.09670 | 0.61390 | 0.94740 | 0.0400* | |
H13A | −0.23290 | 0.84120 | 0.91030 | 0.0440* | |
H13B | −0.12030 | 0.80970 | 1.02250 | 0.0440* | |
H15 | −0.24910 | 1.11020 | 0.85960 | 0.0440* | |
H16 | −0.16480 | 1.33950 | 0.74280 | 0.0480* | |
H17 | 0.06110 | 1.35320 | 0.66310 | 0.0450* | |
H18 | 0.20050 | 1.13580 | 0.70210 | 0.0350* | |
H20 | 0.86120 | 0.91130 | 0.53580 | 0.0260* | |
H22A | 0.84870 | 1.37910 | 0.47840 | 0.0420* | |
H22B | 0.81610 | 1.38580 | 0.33560 | 0.0420* | |
H22C | 0.97260 | 1.37860 | 0.38140 | 0.0420* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0177 (2) | 0.0149 (2) | 0.0232 (2) | 0.0008 (1) | 0.0016 (1) | −0.0071 (1) |
O1 | 0.0221 (5) | 0.0214 (5) | 0.0509 (7) | −0.0001 (4) | 0.0105 (4) | −0.0159 (5) |
O2 | 0.0224 (4) | 0.0198 (5) | 0.0310 (5) | 0.0003 (4) | 0.0032 (4) | −0.0081 (4) |
O3 | 0.0204 (4) | 0.0180 (5) | 0.0359 (6) | −0.0037 (4) | 0.0039 (4) | −0.0075 (4) |
N1 | 0.0172 (5) | 0.0147 (5) | 0.0251 (5) | 0.0007 (4) | 0.0011 (4) | −0.0082 (4) |
N2 | 0.0197 (5) | 0.0161 (5) | 0.0242 (6) | 0.0011 (4) | 0.0011 (4) | −0.0080 (4) |
N3 | 0.0198 (5) | 0.0170 (5) | 0.0258 (6) | 0.0012 (4) | 0.0021 (4) | −0.0086 (4) |
C1 | 0.0174 (5) | 0.0184 (6) | 0.0269 (7) | −0.0008 (5) | 0.0006 (5) | −0.0090 (5) |
C2 | 0.0173 (5) | 0.0175 (6) | 0.0232 (6) | 0.0013 (4) | −0.0009 (4) | −0.0085 (5) |
C3 | 0.0190 (5) | 0.0153 (5) | 0.0189 (6) | 0.0019 (4) | −0.0021 (4) | −0.0067 (5) |
C4 | 0.0158 (5) | 0.0145 (6) | 0.0255 (6) | 0.0007 (4) | 0.0032 (4) | −0.0082 (5) |
C5 | 0.0269 (6) | 0.0208 (6) | 0.0230 (6) | −0.0017 (5) | 0.0002 (5) | −0.0079 (5) |
C6 | 0.0331 (7) | 0.0254 (7) | 0.0317 (8) | −0.0063 (6) | 0.0014 (6) | −0.0150 (6) |
C7 | 0.0312 (7) | 0.0177 (6) | 0.0351 (8) | −0.0037 (5) | 0.0070 (6) | −0.0118 (6) |
C8 | 0.0310 (7) | 0.0187 (6) | 0.0268 (7) | 0.0020 (5) | 0.0032 (5) | −0.0051 (5) |
C9 | 0.0238 (6) | 0.0210 (6) | 0.0255 (7) | 0.0015 (5) | −0.0009 (5) | −0.0093 (5) |
C10 | 0.0196 (6) | 0.0175 (6) | 0.0202 (6) | −0.0001 (5) | 0.0006 (4) | −0.0084 (5) |
C11 | 0.0232 (6) | 0.0197 (6) | 0.0282 (7) | −0.0013 (5) | 0.0050 (5) | −0.0046 (5) |
C12 | 0.0234 (7) | 0.0295 (8) | 0.0400 (9) | −0.0071 (6) | 0.0032 (6) | −0.0042 (6) |
C13 | 0.0218 (7) | 0.0440 (9) | 0.0346 (8) | 0.0017 (6) | 0.0088 (6) | −0.0061 (7) |
C14 | 0.0227 (6) | 0.0355 (8) | 0.0237 (7) | 0.0064 (6) | −0.0008 (5) | −0.0132 (6) |
C15 | 0.0289 (7) | 0.0483 (10) | 0.0359 (8) | 0.0159 (7) | −0.0031 (6) | −0.0216 (8) |
C16 | 0.0446 (9) | 0.0360 (9) | 0.0442 (10) | 0.0217 (7) | −0.0139 (7) | −0.0239 (8) |
C17 | 0.0476 (9) | 0.0214 (7) | 0.0460 (10) | 0.0071 (7) | −0.0107 (7) | −0.0153 (7) |
C18 | 0.0293 (7) | 0.0211 (7) | 0.0382 (8) | 0.0016 (5) | −0.0029 (6) | −0.0137 (6) |
C19 | 0.0213 (6) | 0.0216 (6) | 0.0243 (6) | 0.0035 (5) | −0.0020 (5) | −0.0120 (5) |
C20 | 0.0185 (6) | 0.0193 (6) | 0.0276 (7) | 0.0005 (5) | 0.0003 (5) | −0.0088 (5) |
C21 | 0.0202 (6) | 0.0193 (6) | 0.0226 (6) | −0.0026 (5) | −0.0001 (5) | −0.0066 (5) |
C22 | 0.0257 (6) | 0.0179 (6) | 0.0379 (8) | −0.0050 (5) | 0.0038 (6) | −0.0066 (6) |
S1—C2 | 1.7470 (13) | C14—C19 | 1.4054 (19) |
S1—C3 | 1.7614 (14) | C15—C16 | 1.376 (3) |
O1—C1 | 1.2104 (17) | C16—C17 | 1.388 (2) |
O2—C21 | 1.2147 (16) | C17—C18 | 1.383 (2) |
O3—C21 | 1.3354 (16) | C18—C19 | 1.399 (2) |
O3—C22 | 1.4475 (19) | C20—C21 | 1.471 (2) |
N1—C1 | 1.3841 (17) | C5—H5 | 0.9500 |
N1—C3 | 1.3916 (18) | C6—H6 | 0.9500 |
N1—C4 | 1.4433 (19) | C7—H7 | 0.9500 |
N2—N3 | 1.4069 (17) | C8—H8 | 0.9500 |
N2—C3 | 1.2810 (16) | C9—H9 | 0.9500 |
N3—C10 | 1.2912 (16) | C11—H11A | 0.9900 |
C1—C2 | 1.498 (2) | C11—H11B | 0.9900 |
C2—C20 | 1.3392 (18) | C12—H12A | 0.9900 |
C4—C5 | 1.383 (2) | C12—H12B | 0.9900 |
C4—C9 | 1.3817 (19) | C13—H13A | 0.9900 |
C5—C6 | 1.390 (2) | C13—H13B | 0.9900 |
C6—C7 | 1.384 (2) | C15—H15 | 0.9500 |
C7—C8 | 1.388 (2) | C16—H16 | 0.9500 |
C8—C9 | 1.392 (2) | C17—H17 | 0.9500 |
C10—C11 | 1.503 (2) | C18—H18 | 0.9500 |
C10—C19 | 1.480 (2) | C20—H20 | 0.9500 |
C11—C12 | 1.526 (2) | C22—H22A | 0.9800 |
C12—C13 | 1.522 (3) | C22—H22B | 0.9800 |
C13—C14 | 1.501 (2) | C22—H22C | 0.9800 |
C14—C15 | 1.401 (3) | ||
C2—S1—C3 | 90.54 (6) | O3—C21—C20 | 112.24 (11) |
C21—O3—C22 | 115.22 (11) | C4—C5—H5 | 121.00 |
C1—N1—C3 | 115.28 (12) | C6—C5—H5 | 121.00 |
C1—N1—C4 | 122.38 (11) | C5—C6—H6 | 120.00 |
C3—N1—C4 | 121.19 (10) | C7—C6—H6 | 120.00 |
N3—N2—C3 | 108.54 (11) | C6—C7—H7 | 120.00 |
N2—N3—C10 | 114.88 (12) | C8—C7—H7 | 120.00 |
O1—C1—N1 | 124.49 (13) | C7—C8—H8 | 120.00 |
O1—C1—C2 | 125.72 (12) | C9—C8—H8 | 120.00 |
N1—C1—C2 | 109.78 (11) | C4—C9—H9 | 121.00 |
S1—C2—C1 | 111.61 (9) | C8—C9—H9 | 121.00 |
S1—C2—C20 | 126.19 (12) | C10—C11—H11A | 109.00 |
C1—C2—C20 | 122.19 (12) | C10—C11—H11B | 109.00 |
S1—C3—N1 | 112.60 (9) | C12—C11—H11A | 109.00 |
S1—C3—N2 | 125.31 (11) | C12—C11—H11B | 109.00 |
N1—C3—N2 | 122.08 (13) | H11A—C11—H11B | 108.00 |
N1—C4—C5 | 118.25 (12) | C11—C12—H12A | 110.00 |
N1—C4—C9 | 119.99 (12) | C11—C12—H12B | 110.00 |
C5—C4—C9 | 121.75 (13) | C13—C12—H12A | 110.00 |
C4—C5—C6 | 118.88 (13) | C13—C12—H12B | 110.00 |
C5—C6—C7 | 120.30 (14) | H12A—C12—H12B | 108.00 |
C6—C7—C8 | 120.01 (14) | C12—C13—H13A | 109.00 |
C7—C8—C9 | 120.27 (13) | C12—C13—H13B | 109.00 |
C4—C9—C8 | 118.76 (13) | C14—C13—H13A | 109.00 |
N3—C10—C11 | 124.91 (13) | C14—C13—H13B | 109.00 |
N3—C10—C19 | 116.60 (12) | H13A—C13—H13B | 108.00 |
C11—C10—C19 | 118.49 (11) | C14—C15—H15 | 119.00 |
C10—C11—C12 | 111.39 (12) | C16—C15—H15 | 119.00 |
C11—C12—C13 | 110.22 (13) | C15—C16—H16 | 120.00 |
C12—C13—C14 | 111.71 (13) | C17—C16—H16 | 120.00 |
C13—C14—C15 | 120.61 (13) | C16—C17—H17 | 120.00 |
C13—C14—C19 | 120.99 (14) | C18—C17—H17 | 120.00 |
C15—C14—C19 | 118.40 (15) | C17—C18—H18 | 119.00 |
C14—C15—C16 | 121.64 (15) | C19—C18—H18 | 119.00 |
C15—C16—C17 | 119.89 (17) | C2—C20—H20 | 120.00 |
C16—C17—C18 | 119.62 (17) | C21—C20—H20 | 120.00 |
C17—C18—C19 | 121.12 (14) | O3—C22—H22A | 109.00 |
C10—C19—C14 | 120.36 (13) | O3—C22—H22B | 109.00 |
C10—C19—C18 | 120.29 (12) | O3—C22—H22C | 109.00 |
C14—C19—C18 | 119.32 (14) | H22A—C22—H22B | 109.00 |
C2—C20—C21 | 120.19 (12) | H22A—C22—H22C | 109.00 |
O2—C21—O3 | 124.27 (13) | H22B—C22—H22C | 110.00 |
O2—C21—C20 | 123.49 (12) | ||
C3—S1—C2—C1 | 1.03 (10) | C9—C4—C5—C6 | 0.3 (2) |
C3—S1—C2—C20 | 179.69 (13) | N1—C4—C9—C8 | 177.63 (12) |
C2—S1—C3—N1 | 1.64 (10) | C5—C4—C9—C8 | −1.3 (2) |
C2—S1—C3—N2 | −177.12 (12) | C4—C5—C6—C7 | 1.3 (2) |
C22—O3—C21—O2 | −2.31 (19) | C5—C6—C7—C8 | −1.9 (2) |
C22—O3—C21—C20 | 177.15 (11) | C6—C7—C8—C9 | 0.9 (2) |
C3—N1—C1—O1 | −174.48 (13) | C7—C8—C9—C4 | 0.7 (2) |
C3—N1—C1—C2 | 4.83 (15) | N3—C10—C11—C12 | −149.23 (14) |
C4—N1—C1—O1 | −6.7 (2) | C19—C10—C11—C12 | 30.49 (17) |
C4—N1—C1—C2 | 172.65 (11) | N3—C10—C19—C14 | 177.77 (13) |
C1—N1—C3—S1 | −4.18 (14) | N3—C10—C19—C18 | −0.49 (19) |
C1—N1—C3—N2 | 174.63 (12) | C11—C10—C19—C14 | −1.97 (19) |
C4—N1—C3—S1 | −172.16 (9) | C11—C10—C19—C18 | 179.77 (13) |
C4—N1—C3—N2 | 6.65 (19) | C10—C11—C12—C13 | −56.61 (16) |
C1—N1—C4—C5 | −79.47 (16) | C11—C12—C13—C14 | 54.64 (17) |
C1—N1—C4—C9 | 101.58 (15) | C12—C13—C14—C15 | 152.42 (15) |
C3—N1—C4—C5 | 87.64 (16) | C12—C13—C14—C19 | −26.8 (2) |
C3—N1—C4—C9 | −91.31 (15) | C13—C14—C15—C16 | −178.97 (16) |
C3—N2—N3—C10 | 179.44 (11) | C19—C14—C15—C16 | 0.2 (2) |
N3—N2—C3—S1 | 4.12 (16) | C13—C14—C19—C10 | 0.0 (2) |
N3—N2—C3—N1 | −174.53 (11) | C13—C14—C19—C18 | 178.25 (14) |
N2—N3—C10—C11 | 5.64 (19) | C15—C14—C19—C10 | −179.24 (13) |
N2—N3—C10—C19 | −174.09 (11) | C15—C14—C19—C18 | −1.0 (2) |
O1—C1—C2—S1 | 175.85 (12) | C14—C15—C16—C17 | 0.3 (3) |
O1—C1—C2—C20 | −2.9 (2) | C15—C16—C17—C18 | −0.2 (3) |
N1—C1—C2—S1 | −3.45 (14) | C16—C17—C18—C19 | −0.6 (3) |
N1—C1—C2—C20 | 177.83 (12) | C17—C18—C19—C10 | 179.44 (14) |
S1—C2—C20—C21 | −2.6 (2) | C17—C18—C19—C14 | 1.2 (2) |
C1—C2—C20—C21 | 175.97 (12) | C2—C20—C21—O2 | −4.3 (2) |
N1—C4—C5—C6 | −178.63 (12) | C2—C20—C21—O3 | 176.24 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.95 | 2.59 | 3.3704 (18) | 140 |
C11—H11B···N2 | 0.99 | 2.38 | 2.7466 (18) | 101 |
C20—H20···O3ii | 0.95 | 2.56 | 3.4591 (16) | 159 |
C22—H22C···O1ii | 0.98 | 2.52 | 3.4397 (18) | 157 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H19N3O3S |
Mr | 405.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 9.7078 (6), 9.7134 (6), 11.1061 (7) |
α, β, γ (°) | 67.9810 (9), 88.8400 (9), 85.9840 (9) |
V (Å3) | 968.47 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.28 × 0.16 × 0.09 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2013) |
Tmin, Tmax | 0.83, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17735, 4994, 4325 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.687 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.104, 1.05 |
No. of reflections | 4994 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.30 |
Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2i | 0.95 | 2.59 | 3.3704 (18) | 140 |
C11—H11B···N2 | 0.99 | 2.38 | 2.7466 (18) | 101 |
C20—H20···O3ii | 0.95 | 2.56 | 3.4591 (16) | 159 |
C22—H22C···O1ii | 0.98 | 2.52 | 3.4397 (18) | 157 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+2, −z+1. |
Acknowledgements
Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.
References
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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.
Thiazolidinediones (TZDs) are a pharmacological group of structurally related compounds characterized by a thiazolidinedione ring to which divergent molecular moieties are attached. Many methods have been reoprted for the synthesis of thiazolidinedione-containing compounds and their analogues (Patel et al., 2010; Aneja et al., 2011). The most beneficial effects of TZDs such as rosiglitazone and pioglitazone is the treatment of type II diabetes by lowering blood glucose levels via increasing insulin sensitivity with no hepatic side effects (Gillies & Dunn, 2000; Lenhard & Funk, 2001). They were shown also to reduce cardiovascular risk factors associated with this condition (Edelman, 2003). Recently, an anti-inflammatory potential for TZDs has also been suggested (Desmet et al., 2005). In this context we synthesized the title compound as part of our on-going study in synthesis and biological reactivities of thiazolidinedione scaffold compounds.
In the title compound, (Fig. 1), a puckering analysis (Cremer & Pople, 1975) of the six-membered ring C10/C11/C12/C13/C14/C19 indicates it to adopt the "envelope" conformation with puckering parameters QT = 0.4855 (17) Å, θ = 126.50 (19)° and ϕ = 296.6 (2)°. The 1,3-thiazolidine ring (S1/N1/C1—C3) make dihedral angles of 12.22 (7) and 85.72 (6) °, respectively, with the benzene ring (C14–C19) of the 1,2,3,4-tetrahydronaphthalene ring system and the phenyl ring (C4–C9). The C3–N2–N3–C10, C2–C20–C21–O3 and C20–C21–O3–C22 torsion angles are 179.44 (11), 176.24 (12) and -177.15 (11) °, respectively.
The molecular conformation of the title compound is stabilized by a S1···O2 contact forming a pseudo five-membered ring. In the crystal packing, C—H···O hydrogen bonds connect the molecules generating chains running along [1 0 2] (Table 1, Fig. 2).