Crystal structure of methyl (2Z)-2-[(2Z)-2-(2-cyclo-pentyl-idenehydrazin-1-yl-idene)-4-oxo-3-phenyl-1,3-thia-zolidin-5-yl-idene]ethano-ate.

In the title compound, C17H17N3O3S, the cyclo-pentane ring is disordered over two sets of sites with an occupancy ratio of 0.775 (8):0.225 (8) for the affected atoms. The thia-zolidinyl 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 mol-ecular packing is stabilized by C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional structure.

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 ▸).

Experimental

Crystal data

C17H17N3O3S

M = 343.40

Monoclinic,

a = 5.5215 (3) Å

b = 16.1299 (8) Å

c = 18.7112 (9) Å

β = 93.980 (5)°

V = 1662.42 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.28 × 0.08 × 0.04 mm

Data collection

Agilent Xcalibur, Eos, Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.850, T max = 1.000

11300 measured reflections

5503 independent reflections

3958 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.135

S = 1.02

5503 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: 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 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015017454/tk5388sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017454/tk5388Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015017454/tk5388Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015017454/tk5388fig1.tif

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.

Click here for additional data file.

a . DOI: 10.1107/S2056989015017454/tk5388fig2.tif

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.

CCDC reference: 1425685

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

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

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)

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

Table 1

Hydrogen-bond geometry (, )

Cg4 is the centroid of the C9C14 ring.

DHA	DH	HA	D A	DHA
C13H13O2i	0.93	2.35	3.245(2)	163
C15H15O3ii	0.93	2.56	3.485(2)	172
C17H17AO1ii	0.96	2.42	3.269(2)	147
C3AH3A2Cg4iii	0.97	2.96	3.914(3)	169

Symmetry codes: (i) ; (ii) ; (iii) .