organic compounds
Z)-2-[(2Z)-2-(2-cyclopentylidenehydrazin-1-ylidene)-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene]ethanoate
of methyl (2aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia 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, C17H17N3O3S, the cyclopentane ring is disordered over two sets of sites with an occupancy ratio of 0.775 (8):0.225 (8) for the affected atoms. The thiazolidinyl ring is planar (r.m.s. deviation = 0.024 Å) and forms a dihedral angle of 65.13 (8)° with the attached phenyl ring. The molecular packing is stabilized by C—H⋯O and C—H⋯π interactions, forming a three-dimensional structure.
CCDC reference: 1425685
1. Related literature
For biological properties of thiazole-containing compounds, see: Quiroga et al. (2002); Hutchinson et al. (2002); Hargrave et al. (1983); Patt et al. (1992); Sharma et al. (2009); Jaen et al. (1990); Tsuji & Ishikawa (1994); Bell et al. (1995): Ergenc et al. (1999); Carter et al. (1999); Badorc et al. (1997); Rudolph et al. (2001).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2014); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 1425685
10.1107/S2056989015017454/tk5388sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017454/tk5388Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017454/tk5388Isup3.cml
A mixture of 2-cyclopentylidene-N-phenylhydrazinecarbothioamide (1 mmol, 233 mg) and dimethyl but-2-ynedioate (1 mmol, 142 mg) in ethylacetate (10 ml) was stirred and refluxed at 350 K. The reaction progress was monitored by TLC until completion. On cooling, a solid yellow product was precipitated, filtered off, dried under vacuum and recrystallized from ethanol to afford yellow crystals.
All H atoms were positioned geometrically and constrained to ride on their parent atoms (C—H = 0.93–0.97 Å) with Uiso(H) = 1.2–1.5Ueq(C). The cyclopentyl group was partially disordered over two positions with refined site-occupancies of 0.775 (8): 0.225 (8) . The (3 0 23), (2 1 24), (-1 3 13), (2 11 22), (5 16 3), (2 2 8), (1 3 27), (4 7 18) and (-1 1 14) reflections were omitted owing to poor agreement.
Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. View of the title compound showing only the major component of the disorder. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. | |
Fig. 2. The molecular packing viewed down a axis. The C—H···O interactions are shown as dotted lines with non-participating H atoms omitted for clarity. |
C17H17N3O3S | F(000) = 720 |
Mr = 343.40 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2753 reflections |
a = 5.5215 (3) Å | θ = 4.0–31.8° |
b = 16.1299 (8) Å | µ = 0.22 mm−1 |
c = 18.7112 (9) Å | T = 296 K |
β = 93.980 (5)° | Needle, colourless |
V = 1662.42 (15) Å3 | 0.28 × 0.08 × 0.04 mm |
Z = 4 |
Agilent Xcalibur, Eos, Gemini diffractometer | 5503 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3958 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 32.8°, θmin = 3.3° |
ω scans | h = −8→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −21→23 |
Tmin = 0.850, Tmax = 1.000 | l = −27→28 |
11300 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.058P)2 + 0.3068P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5503 reflections | Δρmax = 0.37 e Å−3 |
222 parameters | Δρmin = −0.32 e Å−3 |
C17H17N3O3S | V = 1662.42 (15) Å3 |
Mr = 343.40 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.5215 (3) Å | µ = 0.22 mm−1 |
b = 16.1299 (8) Å | T = 296 K |
c = 18.7112 (9) Å | 0.28 × 0.08 × 0.04 mm |
β = 93.980 (5)° |
Agilent Xcalibur, Eos, Gemini diffractometer | 5503 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 3958 reflections with I > 2σ(I) |
Tmin = 0.850, Tmax = 1.000 | Rint = 0.036 |
11300 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.37 e Å−3 |
5503 reflections | Δρmin = −0.32 e Å−3 |
222 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 | Occ. (<1) | |
C1A | 1.2932 (4) | 0.58581 (12) | 0.06164 (10) | 0.0431 (5) | 0.775 (8) |
H1A1 | 1.4493 | 0.6135 | 0.0674 | 0.052* | 0.775 (8) |
H1A2 | 1.2277 | 0.5927 | 0.0125 | 0.052* | 0.775 (8) |
C2A | 1.3179 (9) | 0.4943 (2) | 0.0808 (2) | 0.0593 (11) | 0.775 (8) |
H2A1 | 1.2026 | 0.4613 | 0.0515 | 0.071* | 0.775 (8) |
H2A2 | 1.4806 | 0.4746 | 0.0739 | 0.071* | 0.775 (8) |
C3A | 1.2661 (6) | 0.48937 (15) | 0.15730 (14) | 0.0737 (9) | 0.775 (8) |
H3A1 | 1.4154 | 0.4948 | 0.1874 | 0.088* | 0.775 (8) |
H3A2 | 1.1932 | 0.4363 | 0.1673 | 0.088* | 0.775 (8) |
C4A | 1.0943 (4) | 0.55863 (12) | 0.17258 (10) | 0.0435 (5) | 0.775 (8) |
H4A1 | 0.9287 | 0.5385 | 0.1721 | 0.052* | 0.775 (8) |
H4A2 | 1.1381 | 0.5835 | 0.2189 | 0.052* | 0.775 (8) |
C5A | 1.1210 (3) | 0.61997 (10) | 0.11325 (8) | 0.0310 (3) | 0.775 (8) |
C1B | 1.2932 (4) | 0.58581 (12) | 0.06164 (10) | 0.0431 (5) | 0.225 (8) |
H1B1 | 1.4095 | 0.6271 | 0.0482 | 0.052* | 0.225 (8) |
H1B2 | 1.2079 | 0.5633 | 0.0189 | 0.052* | 0.225 (8) |
C2B | 1.413 (3) | 0.5181 (8) | 0.1087 (7) | 0.0593 (11) | 0.225 (8) |
H2B1 | 1.4586 | 0.4726 | 0.0786 | 0.071* | 0.225 (8) |
H2B2 | 1.5594 | 0.5399 | 0.1333 | 0.071* | 0.225 (8) |
C3B | 1.2661 (6) | 0.48937 (15) | 0.15730 (14) | 0.0737 (9) | 0.225 (8) |
H3B1 | 1.3603 | 0.4733 | 0.2008 | 0.088* | 0.225 (8) |
H3B2 | 1.1765 | 0.4414 | 0.1386 | 0.088* | 0.225 (8) |
C4B | 1.0943 (4) | 0.55863 (12) | 0.17258 (10) | 0.0435 (5) | 0.225 (8) |
H4B1 | 0.9287 | 0.5385 | 0.1721 | 0.052* | 0.225 (8) |
H4B2 | 1.1381 | 0.5835 | 0.2189 | 0.052* | 0.225 (8) |
C5B | 1.1210 (3) | 0.61997 (10) | 0.11325 (8) | 0.0310 (3) | 0.225 (8) |
C6 | 0.7150 (3) | 0.76671 (10) | 0.13570 (8) | 0.0265 (3) | |
C7 | 0.3804 (3) | 0.85436 (10) | 0.14664 (8) | 0.0285 (3) | |
C8 | 0.4255 (3) | 0.86289 (10) | 0.06923 (8) | 0.0273 (3) | |
C9 | 0.5666 (3) | 0.78876 (9) | 0.25645 (8) | 0.0252 (3) | |
C10 | 0.7676 (3) | 0.81830 (10) | 0.29704 (9) | 0.0310 (3) | |
H10 | 0.8922 | 0.8450 | 0.2752 | 0.037* | |
C11 | 0.7804 (3) | 0.80745 (11) | 0.37074 (9) | 0.0352 (4) | |
H11 | 0.9157 | 0.8261 | 0.3985 | 0.042* | |
C12 | 0.5927 (3) | 0.76895 (11) | 0.40315 (9) | 0.0352 (4) | |
H12 | 0.5999 | 0.7628 | 0.4527 | 0.042* | |
C13 | 0.3940 (3) | 0.73959 (11) | 0.36148 (9) | 0.0362 (4) | |
H13 | 0.2693 | 0.7129 | 0.3833 | 0.043* | |
C14 | 0.3784 (3) | 0.74947 (10) | 0.28753 (9) | 0.0317 (3) | |
H14 | 0.2443 | 0.7301 | 0.2597 | 0.038* | |
C15 | 0.2862 (3) | 0.91153 (10) | 0.02523 (9) | 0.0299 (3) | |
H15 | 0.1573 | 0.9405 | 0.0428 | 0.036* | |
C16 | 0.3360 (3) | 0.91924 (10) | −0.05004 (9) | 0.0300 (3) | |
C17 | 0.1970 (4) | 0.96748 (13) | −0.16424 (10) | 0.0489 (5) | |
H17A | 0.0682 | 0.9999 | −0.1871 | 0.073* | |
H17B | 0.1937 | 0.9127 | −0.1843 | 0.073* | |
H17C | 0.3501 | 0.9931 | −0.1716 | 0.073* | |
N1 | 1.0203 (3) | 0.69020 (9) | 0.10329 (8) | 0.0364 (3) | |
N2 | 0.8698 (3) | 0.71279 (9) | 0.15868 (7) | 0.0318 (3) | |
N3 | 0.5509 (2) | 0.80198 (8) | 0.18016 (7) | 0.0266 (3) | |
O1 | 0.2219 (2) | 0.88906 (8) | 0.17660 (7) | 0.0404 (3) | |
O2 | 0.5119 (2) | 0.88964 (8) | −0.07551 (7) | 0.0396 (3) | |
O3 | 0.1654 (2) | 0.96244 (8) | −0.08814 (6) | 0.0387 (3) | |
S1 | 0.67455 (7) | 0.80416 (2) | 0.04705 (2) | 0.02957 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0508 (11) | 0.0431 (10) | 0.0379 (9) | 0.0199 (9) | 0.0213 (8) | 0.0066 (8) |
C2A | 0.092 (3) | 0.0466 (18) | 0.042 (2) | 0.0352 (18) | 0.0245 (18) | 0.0039 (13) |
C3A | 0.114 (2) | 0.0509 (13) | 0.0616 (15) | 0.0400 (14) | 0.0432 (16) | 0.0202 (11) |
C4A | 0.0522 (12) | 0.0412 (10) | 0.0390 (10) | 0.0131 (8) | 0.0183 (9) | 0.0094 (8) |
C5A | 0.0314 (8) | 0.0372 (8) | 0.0249 (7) | 0.0078 (6) | 0.0061 (6) | 0.0017 (6) |
C1B | 0.0508 (11) | 0.0431 (10) | 0.0379 (9) | 0.0199 (9) | 0.0213 (8) | 0.0066 (8) |
C2B | 0.092 (3) | 0.0466 (18) | 0.042 (2) | 0.0352 (18) | 0.0245 (18) | 0.0039 (13) |
C3B | 0.114 (2) | 0.0509 (13) | 0.0616 (15) | 0.0400 (14) | 0.0432 (16) | 0.0202 (11) |
C4B | 0.0522 (12) | 0.0412 (10) | 0.0390 (10) | 0.0131 (8) | 0.0183 (9) | 0.0094 (8) |
C5B | 0.0314 (8) | 0.0372 (8) | 0.0249 (7) | 0.0078 (6) | 0.0061 (6) | 0.0017 (6) |
C6 | 0.0262 (7) | 0.0299 (7) | 0.0241 (7) | 0.0031 (6) | 0.0061 (6) | −0.0022 (6) |
C7 | 0.0275 (7) | 0.0308 (8) | 0.0277 (8) | 0.0043 (6) | 0.0055 (6) | −0.0003 (6) |
C8 | 0.0259 (7) | 0.0287 (7) | 0.0281 (7) | 0.0029 (6) | 0.0065 (6) | 0.0000 (6) |
C9 | 0.0258 (7) | 0.0279 (7) | 0.0226 (7) | 0.0045 (5) | 0.0067 (6) | −0.0012 (5) |
C10 | 0.0266 (7) | 0.0393 (9) | 0.0278 (8) | −0.0046 (6) | 0.0069 (6) | −0.0015 (6) |
C11 | 0.0337 (9) | 0.0434 (9) | 0.0282 (8) | −0.0036 (7) | 0.0003 (7) | −0.0051 (7) |
C12 | 0.0416 (9) | 0.0398 (9) | 0.0249 (8) | 0.0028 (7) | 0.0073 (7) | 0.0027 (7) |
C13 | 0.0353 (9) | 0.0414 (9) | 0.0332 (9) | −0.0060 (7) | 0.0120 (7) | 0.0069 (7) |
C14 | 0.0258 (7) | 0.0365 (8) | 0.0328 (8) | −0.0031 (6) | 0.0024 (6) | 0.0010 (6) |
C15 | 0.0286 (8) | 0.0315 (8) | 0.0303 (8) | 0.0074 (6) | 0.0060 (6) | 0.0001 (6) |
C16 | 0.0325 (8) | 0.0261 (7) | 0.0317 (8) | 0.0049 (6) | 0.0032 (6) | 0.0018 (6) |
C17 | 0.0621 (13) | 0.0552 (12) | 0.0294 (9) | 0.0193 (10) | 0.0041 (9) | 0.0069 (8) |
N1 | 0.0401 (8) | 0.0432 (8) | 0.0271 (7) | 0.0175 (6) | 0.0117 (6) | 0.0042 (6) |
N2 | 0.0333 (7) | 0.0376 (7) | 0.0252 (6) | 0.0121 (6) | 0.0072 (5) | −0.0004 (5) |
N3 | 0.0254 (6) | 0.0325 (7) | 0.0224 (6) | 0.0064 (5) | 0.0052 (5) | −0.0004 (5) |
O1 | 0.0394 (7) | 0.0498 (7) | 0.0333 (6) | 0.0199 (6) | 0.0124 (5) | 0.0030 (5) |
O2 | 0.0396 (7) | 0.0462 (7) | 0.0339 (6) | 0.0160 (6) | 0.0100 (5) | 0.0039 (5) |
O3 | 0.0409 (7) | 0.0459 (7) | 0.0294 (6) | 0.0184 (6) | 0.0036 (5) | 0.0053 (5) |
S1 | 0.0303 (2) | 0.0351 (2) | 0.02404 (19) | 0.01015 (15) | 0.00729 (15) | 0.00175 (14) |
C1A—C5A | 1.506 (2) | C8—S1 | 1.7435 (15) |
C1A—C2A | 1.523 (4) | C9—C14 | 1.380 (2) |
C1A—H1A1 | 0.9700 | C9—C10 | 1.385 (2) |
C1A—H1A2 | 0.9700 | C9—N3 | 1.4400 (19) |
C2A—C3A | 1.480 (4) | C10—C11 | 1.387 (2) |
C2A—H2A1 | 0.9700 | C10—H10 | 0.9300 |
C2A—H2A2 | 0.9700 | C11—C12 | 1.384 (2) |
C3A—C4A | 1.506 (3) | C11—H11 | 0.9300 |
C3A—H3A1 | 0.9700 | C12—C13 | 1.384 (3) |
C3A—H3A2 | 0.9700 | C12—H12 | 0.9300 |
C4A—C5A | 1.502 (2) | C13—C14 | 1.389 (2) |
C4A—H4A1 | 0.9700 | C13—H13 | 0.9300 |
C4A—H4A2 | 0.9700 | C14—H14 | 0.9300 |
C5A—N1 | 1.270 (2) | C15—C16 | 1.459 (2) |
C2B—H2B1 | 0.9700 | C15—H15 | 0.9300 |
C2B—H2B2 | 0.9700 | C16—O2 | 1.2094 (19) |
C6—N2 | 1.273 (2) | C16—O3 | 1.3371 (19) |
C6—N3 | 1.3930 (18) | C17—O3 | 1.449 (2) |
C6—S1 | 1.7648 (16) | C17—H17A | 0.9600 |
C7—O1 | 1.2087 (18) | C17—H17B | 0.9600 |
C7—N3 | 1.383 (2) | C17—H17C | 0.9600 |
C7—C8 | 1.493 (2) | N1—N2 | 1.4203 (18) |
C8—C15 | 1.341 (2) | ||
C5A—C1A—C2A | 104.68 (17) | C14—C9—C10 | 121.67 (14) |
C5A—C1A—H1A1 | 110.8 | C14—C9—N3 | 119.38 (14) |
C2A—C1A—H1A1 | 110.8 | C10—C9—N3 | 118.91 (13) |
C5A—C1A—H1A2 | 110.8 | C9—C10—C11 | 119.03 (15) |
C2A—C1A—H1A2 | 110.8 | C9—C10—H10 | 120.5 |
H1A1—C1A—H1A2 | 108.9 | C11—C10—H10 | 120.5 |
C3A—C2A—C1A | 105.0 (2) | C12—C11—C10 | 120.30 (16) |
C3A—C2A—H2A1 | 110.7 | C12—C11—H11 | 119.9 |
C1A—C2A—H2A1 | 110.7 | C10—C11—H11 | 119.9 |
C3A—C2A—H2A2 | 110.7 | C11—C12—C13 | 119.66 (15) |
C1A—C2A—H2A2 | 110.7 | C11—C12—H12 | 120.2 |
H2A1—C2A—H2A2 | 108.8 | C13—C12—H12 | 120.2 |
C2A—C3A—C4A | 108.1 (2) | C12—C13—C14 | 120.90 (15) |
C2A—C3A—H3A1 | 110.1 | C12—C13—H13 | 119.6 |
C4A—C3A—H3A1 | 110.1 | C14—C13—H13 | 119.6 |
C2A—C3A—H3A2 | 110.1 | C9—C14—C13 | 118.43 (15) |
C4A—C3A—H3A2 | 110.1 | C9—C14—H14 | 120.8 |
H3A1—C3A—H3A2 | 108.4 | C13—C14—H14 | 120.8 |
C5A—C4A—C3A | 104.65 (15) | C8—C15—C16 | 120.29 (14) |
C5A—C4A—H4A1 | 110.8 | C8—C15—H15 | 119.9 |
C3A—C4A—H4A1 | 110.8 | C16—C15—H15 | 119.9 |
C5A—C4A—H4A2 | 110.8 | O2—C16—O3 | 123.44 (15) |
C3A—C4A—H4A2 | 110.8 | O2—C16—C15 | 123.85 (15) |
H4A1—C4A—H4A2 | 108.9 | O3—C16—C15 | 112.71 (14) |
N1—C5A—C4A | 129.17 (15) | O3—C17—H17A | 109.5 |
N1—C5A—C1A | 121.44 (15) | O3—C17—H17B | 109.5 |
C4A—C5A—C1A | 109.38 (14) | H17A—C17—H17B | 109.5 |
H2B1—C2B—H2B2 | 107.8 | O3—C17—H17C | 109.5 |
N2—C6—N3 | 121.76 (14) | H17A—C17—H17C | 109.5 |
N2—C6—S1 | 126.11 (12) | H17B—C17—H17C | 109.5 |
N3—C6—S1 | 112.11 (11) | C5A—N1—N2 | 113.21 (13) |
O1—C7—N3 | 124.37 (15) | C6—N2—N1 | 110.00 (13) |
O1—C7—C8 | 125.61 (15) | C7—N3—C6 | 115.42 (13) |
N3—C7—C8 | 110.00 (12) | C7—N3—C9 | 122.16 (12) |
C15—C8—C7 | 121.50 (14) | C6—N3—C9 | 122.32 (13) |
C15—C8—S1 | 126.88 (12) | C16—O3—C17 | 115.13 (13) |
C7—C8—S1 | 111.62 (11) | C8—S1—C6 | 90.72 (7) |
C5A—C1A—C2A—C3A | −26.1 (4) | C4A—C5A—N1—N2 | 2.6 (3) |
C1A—C2A—C3A—C4A | 29.1 (4) | C1A—C5A—N1—N2 | −178.28 (17) |
C2A—C3A—C4A—C5A | −20.2 (4) | N3—C6—N2—N1 | −177.41 (14) |
C3A—C4A—C5A—N1 | −177.5 (2) | S1—C6—N2—N1 | 3.9 (2) |
C3A—C4A—C5A—C1A | 3.2 (3) | C5A—N1—N2—C6 | −158.03 (17) |
C2A—C1A—C5A—N1 | −165.2 (3) | O1—C7—N3—C6 | 178.61 (16) |
C2A—C1A—C5A—C4A | 14.1 (3) | C8—C7—N3—C6 | −2.76 (19) |
O1—C7—C8—C15 | −0.4 (3) | O1—C7—N3—C9 | −4.9 (3) |
N3—C7—C8—C15 | −179.02 (15) | C8—C7—N3—C9 | 173.70 (13) |
O1—C7—C8—S1 | 178.92 (15) | N2—C6—N3—C7 | −174.81 (16) |
N3—C7—C8—S1 | 0.32 (17) | S1—C6—N3—C7 | 4.01 (17) |
C14—C9—C10—C11 | 0.5 (2) | N2—C6—N3—C9 | 8.7 (2) |
N3—C9—C10—C11 | 178.44 (14) | S1—C6—N3—C9 | −172.45 (11) |
C9—C10—C11—C12 | −1.1 (3) | C14—C9—N3—C7 | 66.1 (2) |
C10—C11—C12—C13 | 1.4 (3) | C10—C9—N3—C7 | −111.84 (17) |
C11—C12—C13—C14 | −1.1 (3) | C14—C9—N3—C6 | −117.65 (16) |
C10—C9—C14—C13 | −0.2 (2) | C10—C9—N3—C6 | 64.4 (2) |
N3—C9—C14—C13 | −178.09 (15) | O2—C16—O3—C17 | 3.7 (3) |
C12—C13—C14—C9 | 0.5 (3) | C15—C16—O3—C17 | −176.13 (15) |
C7—C8—C15—C16 | 179.45 (15) | C15—C8—S1—C6 | −179.15 (16) |
S1—C8—C15—C16 | 0.2 (2) | C7—C8—S1—C6 | 1.56 (12) |
C8—C15—C16—O2 | −6.8 (3) | N2—C6—S1—C8 | 175.66 (16) |
C8—C15—C16—O3 | 173.02 (15) | N3—C6—S1—C8 | −3.10 (12) |
Cg4 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O2i | 0.93 | 2.35 | 3.245 (2) | 163 |
C15—H15···O3ii | 0.93 | 2.56 | 3.485 (2) | 172 |
C17—H17A···O1ii | 0.96 | 2.42 | 3.269 (2) | 147 |
C3A—H3A2···Cg4iii | 0.97 | 2.96 | 3.914 (3) | 169 |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x, −y+2, −z; (iii) −x+3/2, y−1/2, −z+1/2. |
Cg4 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O2i | 0.93 | 2.35 | 3.245 (2) | 163 |
C15—H15···O3ii | 0.93 | 2.56 | 3.485 (2) | 172 |
C17—H17A···O1ii | 0.96 | 2.42 | 3.269 (2) | 147 |
C3A—H3A2···Cg4iii | 0.97 | 2.96 | 3.914 (3) | 169 |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x, −y+2, −z; (iii) −x+3/2, y−1/2, −z+1/2. |
Acknowledgements
JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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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.
Thiazoles are important class of heterocyclic compounds, found in many potent biologically active molecules such as sulfathiazol (antimicrobial drug), Ritonavir (antiretroviral drug), Abafungin (antifungal drug), with trade name Abasol cream, and Bleomycine and Tiazofurin (antineoplastic drug). It has been noted over the years that interesting biological activities (Quiroga et al., 2002; Hutchinson et al., 2002) were associated with thiazole derivatives. Applications of thiazoles were found in drug development for the treatment of allergies (Hargrave et al., 1983), hypertension (Patt et al., 1992), inflammation (Sharma et al., 2009), schizophrenia (Jaen et al., 1990), bacteria infection (Tsuji & Ishikawa, 1994), HIV infection (Bell et al., 1995), hypnotics (Ergenc et al., 1999) and for the treatment of pain (Carter et al., 1999), as fibrinogen receptor antagonists with antithrombotic activity (Badorc et al., 1997) and as new inhibitors of bacterial DNA gyrase B (Rudolph et al., 2001). In this context we report in this study the synthesis and crystal structure of the title compound.
The molecular structure of the title compound is shown in Fig. 1. The major and minor components of the disordered cyclopentane ring [0.775 (8):0.225 (8)] adopt an envelope conformations with atoms C2A and C2B as the flap in each component. The puckering parameters are Q(2) 0.274 (3) Å, φ (2) = 42.7 (6)° for major component, and Q(2) 0.253 (8) Å, φ (2) = 209.6 (16)° for minor component. The central 1,3-thiazolidine ring (S1/N3C6–C8) makes a dihedral angle of 65.13 (8)° with the phenyl ring (C9–C14).
In the crystal, C—H···O and C—H···π interactions stabilize the molecular packing, forming a three-dimensional network, Fig. 2 and Table 1.