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

Mague, J.T.; Akkurt, M.; Mohamed, S.K.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536814005285

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o436-o437

doi:10.1107/S1600536814005285

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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

Joel T. Mague,^a Mehmet Akkurt,^b Shaaban K. Mohamed,^c,^d Alaa A. Hassan ^d and Mustafa R. Albayati ^e ^*

^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

(Received 6 March 2014; accepted 7 March 2014; online 15 March 2014)

In the title compound, C₂₂H₁₉N₃O₃S, the six-membered ring of the 1,2,3,4-tetrahydronaphthalene ring system adopts an envelope conformation 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

C₂₂H₁₉N₃O₃S
M_r = 405.47
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.05
4994 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) -x+1, -y+2, -z+1; (ii) -x+2, -y+2, -z+1.

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 ).

Supporting information

CCDC reference: 990619

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814005285/bt6966sup1.cif

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

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

checkCIF report

Comment top

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 Q_T = 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).

Related literature top

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 top

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.

Computing details top

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

Figures top

	Fig. 1. Perspective view of the title molecule with 50% probability ellipsoids.
	Fig. 2. Packing and hydrogen-bonding interactions of the title compound viewed down the a axis. H atoms not involved in H bonding are omitted for clarity.

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 top

Crystal data top

C₂₂H₁₉N₃O₃S	Z = 2
M_r = 405.47	F(000) = 424
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART APEX CCD diffractometer	4994 independent reflections
Radiation source: fine-focus sealed tube	4325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 8.3660 pixels mm^-1	θ_max = 29.2°, θ_min = 2.0°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −13→13
T_min = 0.83, T_max = 0.98	l = −14→15
17735 measured reflections

Refinement top

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(F_o²) + (0.0495P)² + 0.3384P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4994 reflections	Δρ_max = 0.39 e Å⁻³
263 parameters	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₁₉N₃O₃S	γ = 85.9840 (9)°
M_r = 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)°

Data collection top

Bruker SMART APEX CCD diffractometer	4994 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	4325 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.98	R_int = 0.036
17735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.39 e Å⁻³
4994 reflections	Δρ_min = −0.30 e Å⁻³
263 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.83, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	17735, 4994, 4325
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

Aneja, D. K., Lohan, P., Arora, S., Sharma, C., Aneja, K. R. & Prakash, O. (2011). Org. Med. Chem. Lett. 1, 1–11. CrossRef PubMed Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 70| Part 4| April 2014| Pages o436-o437

doi:10.1107/S1600536814005285

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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