Methyl 2-((2Z,5Z)-4-oxo-3-phenyl-2-{2-[(1E)-1,2,3,4-tetra-hydro-naphthalen-1-yl-idene]hydrazin-1-yl-idene}-1,3-thia-zolidin-5-yl-idene)acetate.

In the title compound, C22H19N3O3S, the six-membered ring of the 1,2,3,4-tetra-hydro-naphthalene ring system adopts an envelope conformation with the central CH2 C atom as the flap. The mol-ecular conformation is stabilized by an S⋯O contact, forming a pseudo-five-membered ring. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into chains propagating along [102].

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

C22H19N3O3S

M = 405.47

Triclinic,

a = 9.7078 (6) Å

b = 9.7134 (6) Å

c = 11.1061 (7) Å

α = 67.9810 (9)°

β = 88.8400 (9)°

γ = 85.9840 (9)°

V = 968.47 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 150 K

0.28 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.83, T max = 0.98

17735 measured reflections

4994 independent reflections

4325 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.05

4994 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814005285/bt6966sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005285/bt6966Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005285/bt6966Isup3.cml

CCDC reference: 990619

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

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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .