Literature DB >> 24109387

2-(4-Oxo-3-phenyl-1,3-thia-zolidin-2-yl-idene)propanedi-nitrile.

Mehmet Akkurt¹, Ahmed M M El-Saghier, Sabry H H Younes, Peter N Horton, Mustafa R Albayati.

Abstract

In the title compound, C12H7N3OS, the five-membered 1,3-thia-zolidine ring is nearly planar [maximum deviation = 0.032 (2) Å] and makes a dihedral angle of 84.14 (9)° with the phenyl ring. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds into infinite chains along [-101]. C-H⋯π inter-actions contribute to the arrangement of the mol-ecules into layers parallel to (101).

Entities: CellLine Chemical Disease Species

Year: 2013 PMID： 24109387 PMCID： PMC3793800 DOI： 10.1107/S1600536813018308

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the diverse biological applications of thiazolidinone-containing compounds, see, for example: Bouzroura et al. (2010 ▶); Abhinit et al. (2009 ▶); Naeem et al. (2009 ▶); Sharma et al. (2009 ▶); Mistry & Desai (2004 ▶); Ramalakshmi et al. (2009 ▶); Turgut et al. (2007 ▶). For the synthesis of similar compounds, see: Farhat et al. (2007 ▶). For similar structures, see: Pomés Hernández et al. (1996 ▶).

Experimental

Crystal data

C12H7N3OS M = 241.28 Monoclinic, a = 16.979 (9) Å b = 9.407 (5) Å c = 7.034 (4) Å β = 103.927 (11)° V = 1090.5 (10) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 100 K 0.24 × 0.12 × 0.04 mm

Data collection

Rigaku AFC12 (Right) diffractometer Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T min = 0.944, T max = 1.000 3632 measured reflections 1986 independent reflections 1955 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.022 wR(F 2) = 0.061 S = 1.08 1986 reflections 154 parameters 2 restraints H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.18 e Å−3 Absolute structure: Flack x parameter determined using 718 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons & Flack, 2004 ▶) Flack parameter: 0.03 (3) Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (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/S1600536813018308/hg5329sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018308/hg5329Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813018308/hg5329Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₂H₇N₃OS	F(000) = 496
M_r = 241.28	D_x = 1.470 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: C -2yc	Cell parameters from 1540 reflections
a = 16.979 (9) Å	θ = 2.5–29.9°
b = 9.407 (5) Å	µ = 0.28 mm⁻¹
c = 7.034 (4) Å	T = 100 K
β = 103.927 (11)°	Blade, pale brown
V = 1090.5 (10) Å³	0.24 × 0.12 × 0.04 mm
Z = 4

Rigaku AFC12 (Right) diffractometer	1986 independent reflections
Radiation source: Rotating Anode	1955 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	R_int = 0.015
profile data from ω–scans	θ_max = 27.5°, θ_min = 3.7°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −21→21
T_min = 0.944, T_max = 1.000	k = −12→11
3632 measured reflections	l = −9→9

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.022	W = 1/[Σ²(F_o²) + (0.0377P)² + 0.4177P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.061	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.19 e Å⁻³
1986 reflections	Δρ_min = −0.18 e Å⁻³
154 parameters	Absolute structure: Flack x parameter determined using 718 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
2 restraints	Flack parameter: 0.03 (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	U_iso*/U_eq
S1	0.14621 (4)	0.73643 (4)	0.22599 (6)	0.0152 (1)
O1	0.23305 (9)	0.57530 (15)	−0.1843 (2)	0.0179 (4)
N1	0.27769 (10)	0.68589 (17)	0.1115 (2)	0.0120 (4)
N2	0.45449 (12)	0.8278 (2)	0.5329 (3)	0.0210 (6)
N3	0.22781 (12)	0.91044 (19)	0.6832 (3)	0.0209 (5)
C1	0.25143 (14)	0.74325 (18)	0.2647 (3)	0.0122 (5)
C2	0.21787 (12)	0.6278 (2)	−0.0407 (3)	0.0138 (5)
C3	0.13519 (12)	0.6388 (2)	0.0001 (3)	0.0162 (6)
C4	0.29897 (12)	0.8016 (2)	0.4321 (3)	0.0135 (5)
C5	0.38554 (13)	0.8131 (2)	0.4803 (3)	0.0146 (5)
C6	0.25922 (12)	0.8615 (2)	0.5710 (3)	0.0149 (5)
C7	0.36194 (12)	0.6787 (2)	0.1046 (3)	0.0128 (5)
C8	0.40498 (13)	0.5558 (2)	0.1676 (3)	0.0157 (6)
C9	0.48583 (13)	0.5491 (2)	0.1579 (3)	0.0205 (6)
C10	0.52117 (14)	0.6634 (3)	0.0838 (3)	0.0218 (6)
C11	0.47629 (14)	0.7848 (3)	0.0200 (3)	0.0207 (6)
C12	0.39603 (13)	0.7932 (2)	0.0298 (3)	0.0159 (6)
H3A	0.11320	0.54270	0.01290	0.0190*
H3B	0.09750	0.68900	−0.10840	0.0190*
H8	0.38000	0.47790	0.21620	0.0190*
H9	0.51700	0.46640	0.20200	0.0250*
H10	0.57630	0.65810	0.07680	0.0260*
H11	0.50070	0.86240	−0.03050	0.0250*
H12	0.36490	0.87600	−0.01390	0.0190*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0091 (2)	0.0180 (2)	0.0189 (2)	0.0011 (2)	0.0041 (2)	−0.0031 (2)
O1	0.0177 (7)	0.0190 (7)	0.0177 (8)	−0.0020 (6)	0.0058 (6)	−0.0049 (6)
N1	0.0093 (8)	0.0128 (7)	0.0142 (8)	0.0004 (6)	0.0032 (6)	−0.0010 (6)
N2	0.0165 (10)	0.0269 (9)	0.0201 (10)	−0.0019 (8)	0.0055 (8)	−0.0041 (7)
N3	0.0170 (9)	0.0251 (9)	0.0210 (10)	−0.0010 (8)	0.0052 (8)	−0.0074 (8)
C1	0.0116 (9)	0.0108 (8)	0.0149 (10)	0.0013 (7)	0.0044 (8)	0.0018 (7)
C2	0.0126 (9)	0.0115 (8)	0.0166 (9)	0.0007 (7)	0.0024 (8)	0.0016 (7)
C3	0.0117 (10)	0.0203 (9)	0.0157 (10)	−0.0015 (8)	0.0018 (8)	−0.0019 (8)
C4	0.0113 (10)	0.0132 (8)	0.0161 (10)	0.0013 (7)	0.0034 (8)	−0.0010 (7)
C5	0.0159 (11)	0.0142 (8)	0.0143 (9)	−0.0007 (8)	0.0046 (8)	−0.0016 (7)
C6	0.0109 (9)	0.0150 (9)	0.0173 (10)	−0.0017 (8)	0.0002 (8)	−0.0018 (7)
C7	0.0097 (9)	0.0167 (8)	0.0126 (9)	−0.0010 (7)	0.0040 (8)	−0.0034 (7)
C8	0.0158 (10)	0.0183 (9)	0.0136 (10)	0.0013 (8)	0.0046 (8)	−0.0003 (7)
C9	0.0152 (10)	0.0284 (10)	0.0172 (10)	0.0070 (9)	0.0026 (8)	−0.0017 (8)
C10	0.0108 (9)	0.0389 (12)	0.0162 (10)	0.0003 (9)	0.0044 (8)	−0.0052 (9)
C11	0.0158 (11)	0.0299 (11)	0.0175 (11)	−0.0080 (9)	0.0064 (9)	−0.0001 (9)
C12	0.0141 (10)	0.0176 (9)	0.0145 (10)	−0.0015 (8)	0.0008 (9)	0.0005 (7)

S1—C1	1.742 (3)	C7—C12	1.385 (3)
S1—C3	1.806 (2)	C8—C9	1.392 (3)
O1—C2	1.207 (3)	C9—C10	1.392 (3)
N1—C1	1.372 (3)	C10—C11	1.386 (4)
N1—C2	1.398 (3)	C11—C12	1.383 (3)
N1—C7	1.445 (3)	C3—H3A	0.9900
N2—C5	1.148 (3)	C3—H3B	0.9900
N3—C6	1.150 (3)	C8—H8	0.9500
C1—C4	1.372 (3)	C9—H9	0.9500
C2—C3	1.503 (3)	C10—H10	0.9500
C4—C5	1.431 (3)	C11—H11	0.9500
C4—C6	1.430 (3)	C12—H12	0.9500
C7—C8	1.382 (3)

C1—S1—C3	92.38 (10)	C8—C9—C10	120.15 (19)
C1—N1—C2	116.22 (18)	C9—C10—C11	120.3 (2)
C1—N1—C7	123.81 (17)	C10—C11—C12	120.2 (2)
C2—N1—C7	119.93 (16)	C7—C12—C11	118.8 (2)
S1—C1—N1	112.19 (15)	S1—C3—H3A	110.00
S1—C1—C4	121.22 (17)	S1—C3—H3B	110.00
N1—C1—C4	126.6 (2)	C2—C3—H3A	110.00
O1—C2—N1	122.62 (19)	C2—C3—H3B	110.00
O1—C2—C3	125.85 (19)	H3A—C3—H3B	109.00
N1—C2—C3	111.53 (17)	C7—C8—H8	121.00
S1—C3—C2	107.42 (14)	C9—C8—H8	121.00
C1—C4—C5	126.3 (2)	C8—C9—H9	120.00
C1—C4—C6	117.9 (2)	C10—C9—H9	120.00
C5—C4—C6	115.80 (18)	C9—C10—H10	120.00
N2—C5—C4	174.4 (2)	C11—C10—H10	120.00
N3—C6—C4	179.4 (2)	C10—C11—H11	120.00
N1—C7—C8	118.67 (18)	C12—C11—H11	120.00
N1—C7—C12	118.95 (18)	C7—C12—H12	121.00
C8—C7—C12	122.4 (2)	C11—C12—H12	121.00
C7—C8—C9	118.27 (18)

C3—S1—C1—N1	4.42 (14)	N1—C1—C4—C5	−0.5 (3)
C3—S1—C1—C4	−175.95 (16)	S1—C1—C4—C6	−2.2 (3)
C1—S1—C3—C2	−4.78 (14)	S1—C1—C4—C5	179.94 (15)
C7—N1—C1—S1	179.56 (14)	N1—C1—C4—C6	177.33 (18)
C2—N1—C1—C4	177.70 (18)	N1—C2—C3—S1	4.19 (19)
C7—N1—C1—C4	0.0 (3)	O1—C2—C3—S1	−176.30 (17)
C7—N1—C2—C3	176.70 (16)	N1—C7—C8—C9	179.13 (17)
C1—N1—C2—O1	179.35 (18)	C12—C7—C8—C9	1.1 (3)
C7—N1—C2—O1	−2.8 (3)	N1—C7—C12—C11	−178.78 (18)
C2—N1—C1—S1	−2.7 (2)	C8—C7—C12—C11	−0.8 (3)
C2—N1—C7—C12	94.9 (2)	C7—C8—C9—C10	−0.9 (3)
C1—N1—C7—C8	94.5 (2)	C8—C9—C10—C11	0.3 (3)
C1—N1—C2—C3	−1.1 (2)	C9—C10—C11—C12	0.1 (3)
C1—N1—C7—C12	−87.5 (2)	C10—C11—C12—C7	0.2 (3)
C2—N1—C7—C8	−83.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N3ⁱ	0.95	2.58	3.479 (4)	157
C8—H8···Cg2ⁱⁱ	0.95	2.96	3.610 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯N3ⁱ	0.95	2.58	3.479 (4)	157
C8—H8⋯Cg2ⁱⁱ	0.95	2.96	3.610 (3)	127

Symmetry codes: (i) ; (ii) .

3 in total

2-(4-Oxo-3-phenyl-1,3-thia-zolidin-2-yl-idene)propanedi-nitrile.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. Synthesis of new pyrazolothiazole derivatives from 4-thiazolidinones.

3. Structure validation in chemical crystallography.