Literature DB >> 22090953

2-(4-Bromo-phen-yl)-3-(4-hy-droxy-phen-yl)-1,3-thia-zolidin-4-one.

Jasmine P Vennila, D John Thiruvadigal, Helen P Kavitha, G Chakkaravarthi, V Manivannan.

Abstract

In the title compound, C(15)H(12)BrNO(2)S, the dihedral angle between the two aromatic rings is 87.81 (8)°. The five-membered thia-zolidine ring has an envelope conformation, with the S atom displaced by 0.4545 (7) Å from the mean plane of the other four ring atoms. The crystal structure exhibits O-H⋯O, C-H⋯O, C-H⋯Br and C-H⋯ π inter-actions.

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 22090953 PMCID： PMC3212296 DOI： 10.1107/S1600536811025281

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

Related literature

For the biolgical activity of thiazolidine derivatives, see: Chen et al. (2000 ▶); Jacop & Kutty (2004 ▶); Kalia et al. (2007 ▶); Vicentini et al. (1998 ▶); Vigorita et al. (1992 ▶). For bond-length data see: Allen et al. (1987 ▶). For related structures, see: Akkurt et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C15H12BrNO2S M = 350.23 Orthorhombic, a = 13.3367 (6) Å b = 12.6292 (5) Å c = 17.1230 (6) Å V = 2884.1 (2) Å3 Z = 8 Mo Kα radiation μ = 3.00 mm−1 T = 295 K 0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.467, T max = 0.586 18957 measured reflections 3617 independent reflections 2317 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.087 S = 1.02 3617 reflections 181 parameters H-atom parameters constrained Δρmax = 0.45 e Å−3 Δρmin = −0.47 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025281/bt5562sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025281/bt5562Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811025281/bt5562Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₂BrNO₂S	F(000) = 1408
M_r = 350.23	D_x = 1.613 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4654 reflections
a = 13.3367 (6) Å	θ = 2.4–23.8°
b = 12.6292 (5) Å	µ = 3.00 mm⁻¹
c = 17.1230 (6) Å	T = 295 K
V = 2884.1 (2) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII diffractometer	3617 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
graphite	R_int = 0.031
ω and φ scans	θ_max = 28.4°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
T_min = 0.467, T_max = 0.586	k = −16→16
18957 measured reflections	l = −16→22

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0332P)² + 1.5996P] where P = (F_o² + 2F_c²)/3
3617 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

	x	y	z	U_iso*/U_eq
C1	0.63473 (19)	0.1392 (2)	0.12609 (17)	0.0510 (7)
H1A	0.6916	0.1565	0.0932	0.061*
H1B	0.6280	0.0628	0.1279	0.061*
C2	0.54086 (16)	0.18813 (18)	0.09361 (15)	0.0344 (5)
C3	0.52231 (15)	0.23237 (19)	0.22967 (13)	0.0328 (5)
H3	0.5202	0.3035	0.2525	0.039*
C4	0.46182 (16)	0.15917 (18)	0.28031 (13)	0.0316 (5)
C5	0.41708 (17)	0.06902 (18)	0.25054 (14)	0.0342 (5)
H5	0.4201	0.0555	0.1972	0.041*
C6	0.36796 (18)	−0.00109 (19)	0.29911 (15)	0.0387 (6)
H6	0.3372	−0.0612	0.2788	0.046*
C7	0.36517 (19)	0.0191 (2)	0.37752 (15)	0.0427 (6)
C8	0.4075 (2)	0.1078 (2)	0.40845 (16)	0.0515 (7)
H8	0.4044	0.1204	0.4619	0.062*
C9	0.4548 (2)	0.1784 (2)	0.35973 (15)	0.0459 (7)
H9	0.4825	0.2399	0.3804	0.055*
C10	0.39180 (15)	0.28732 (16)	0.13260 (12)	0.0262 (5)
C11	0.31686 (16)	0.23068 (17)	0.09663 (13)	0.0305 (5)
H11	0.3274	0.1603	0.0830	0.037*
C12	0.22563 (16)	0.27854 (18)	0.08068 (13)	0.0324 (5)
H12	0.1745	0.2400	0.0571	0.039*
C13	0.21067 (15)	0.38358 (18)	0.09987 (13)	0.0313 (5)
C14	0.28555 (17)	0.43972 (18)	0.13648 (15)	0.0373 (6)
H14	0.2751	0.5101	0.1502	0.045*
C15	0.37581 (17)	0.39194 (18)	0.15282 (14)	0.0351 (5)
H15	0.4263	0.4301	0.1776	0.042*
N1	0.48688 (12)	0.23846 (14)	0.14893 (10)	0.0290 (4)
O1	0.51648 (12)	0.18202 (13)	0.02472 (10)	0.0432 (4)
O2	0.12206 (12)	0.43423 (13)	0.08407 (11)	0.0472 (5)
H2	0.0887	0.3982	0.0539	0.057*
S1	0.65353 (5)	0.19057 (6)	0.22246 (4)	0.04894 (19)
Br1	0.29816 (3)	−0.07918 (3)	0.44309 (2)	0.07795 (16)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0342 (14)	0.0612 (17)	0.0575 (18)	0.0169 (13)	0.0023 (12)	0.0021 (14)
C2	0.0277 (12)	0.0379 (12)	0.0376 (16)	0.0002 (10)	0.0076 (11)	0.0026 (11)
C3	0.0271 (11)	0.0393 (12)	0.0320 (14)	0.0020 (10)	−0.0051 (10)	−0.0013 (10)
C4	0.0285 (11)	0.0418 (13)	0.0244 (13)	0.0066 (10)	−0.0036 (9)	−0.0008 (10)
C5	0.0393 (13)	0.0402 (12)	0.0229 (12)	0.0040 (11)	−0.0011 (10)	0.0000 (11)
C6	0.0402 (14)	0.0346 (13)	0.0413 (16)	0.0070 (11)	0.0006 (11)	0.0037 (11)
C7	0.0436 (14)	0.0497 (15)	0.0349 (16)	0.0170 (12)	0.0104 (12)	0.0136 (13)
C8	0.0581 (18)	0.0711 (19)	0.0254 (14)	0.0138 (15)	0.0042 (13)	−0.0003 (14)
C9	0.0483 (15)	0.0560 (16)	0.0335 (16)	0.0013 (13)	−0.0020 (12)	−0.0098 (13)
C10	0.0226 (10)	0.0330 (11)	0.0230 (12)	0.0013 (9)	0.0013 (9)	0.0011 (9)
C11	0.0320 (12)	0.0290 (11)	0.0305 (13)	0.0008 (10)	0.0002 (10)	−0.0040 (10)
C12	0.0258 (11)	0.0405 (13)	0.0310 (13)	−0.0017 (10)	−0.0041 (9)	−0.0098 (10)
C13	0.0253 (11)	0.0421 (12)	0.0265 (13)	0.0064 (10)	−0.0012 (9)	−0.0062 (10)
C14	0.0344 (13)	0.0331 (12)	0.0442 (15)	0.0038 (10)	−0.0071 (11)	−0.0118 (11)
C15	0.0264 (11)	0.0388 (13)	0.0400 (15)	−0.0039 (10)	−0.0059 (10)	−0.0062 (11)
N1	0.0234 (9)	0.0362 (10)	0.0273 (11)	0.0037 (8)	−0.0009 (8)	0.0024 (8)
O1	0.0371 (9)	0.0622 (11)	0.0304 (11)	0.0067 (8)	0.0078 (8)	−0.0037 (8)
O2	0.0324 (9)	0.0557 (11)	0.0534 (11)	0.0145 (8)	−0.0157 (8)	−0.0223 (9)
S1	0.0268 (3)	0.0699 (5)	0.0501 (5)	0.0060 (3)	−0.0060 (3)	0.0099 (4)
Br1	0.1055 (3)	0.0617 (2)	0.0667 (3)	0.02192 (19)	0.0415 (2)	0.03136 (17)

C1—C2	1.503 (3)	C7—Br1	1.897 (2)
C1—S1	1.791 (3)	C8—C9	1.375 (4)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—H9	0.9300
C2—O1	1.226 (3)	C10—C11	1.375 (3)
C2—N1	1.349 (3)	C10—C15	1.382 (3)
C3—N1	1.463 (3)	C10—N1	1.438 (3)
C3—C4	1.502 (3)	C11—C12	1.386 (3)
C3—S1	1.832 (2)	C11—H11	0.9300
C3—H3	0.9800	C12—C13	1.381 (3)
C4—C5	1.383 (3)	C12—H12	0.9300
C4—C9	1.385 (3)	C13—O2	1.371 (3)
C5—C6	1.380 (3)	C13—C14	1.376 (3)
C5—H5	0.9300	C14—C15	1.375 (3)
C6—C7	1.367 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.361 (4)	O2—H2	0.8200

C2—C1—S1	107.98 (18)	C7—C8—H8	120.4
C2—C1—H1A	110.1	C9—C8—H8	120.4
S1—C1—H1A	110.1	C8—C9—C4	120.9 (2)
C2—C1—H1B	110.1	C8—C9—H9	119.6
S1—C1—H1B	110.1	C4—C9—H9	119.6
H1A—C1—H1B	108.4	C11—C10—C15	119.83 (19)
O1—C2—N1	124.3 (2)	C11—C10—N1	120.33 (19)
O1—C2—C1	123.5 (2)	C15—C10—N1	119.84 (19)
N1—C2—C1	112.2 (2)	C10—C11—C12	120.0 (2)
N1—C3—C4	113.86 (18)	C10—C11—H11	120.0
N1—C3—S1	105.06 (14)	C12—C11—H11	120.0
C4—C3—S1	111.99 (15)	C13—C12—C11	119.9 (2)
N1—C3—H3	108.6	C13—C12—H12	120.0
C4—C3—H3	108.6	C11—C12—H12	120.0
S1—C3—H3	108.6	O2—C13—C14	118.4 (2)
C5—C4—C9	118.5 (2)	O2—C13—C12	121.7 (2)
C5—C4—C3	121.7 (2)	C14—C13—C12	119.9 (2)
C9—C4—C3	119.7 (2)	C15—C14—C13	120.1 (2)
C6—C5—C4	120.7 (2)	C15—C14—H14	119.9
C6—C5—H5	119.6	C13—C14—H14	119.9
C4—C5—H5	119.6	C14—C15—C10	120.2 (2)
C7—C6—C5	119.0 (2)	C14—C15—H15	119.9
C7—C6—H6	120.5	C10—C15—H15	119.9
C5—C6—H6	120.5	C2—N1—C10	122.44 (18)
C8—C7—C6	121.6 (2)	C2—N1—C3	117.80 (18)
C8—C7—Br1	120.2 (2)	C10—N1—C3	119.42 (17)
C6—C7—Br1	118.2 (2)	C13—O2—H2	109.5
C7—C8—C9	119.2 (2)	C1—S1—C3	91.88 (11)

S1—C1—C2—O1	168.02 (19)	O2—C13—C14—C15	−179.5 (2)
S1—C1—C2—N1	−12.4 (3)	C12—C13—C14—C15	1.1 (4)
N1—C3—C4—C5	32.4 (3)	C13—C14—C15—C10	0.0 (4)
S1—C3—C4—C5	−86.6 (2)	C11—C10—C15—C14	−0.6 (3)
N1—C3—C4—C9	−151.3 (2)	N1—C10—C15—C14	179.1 (2)
S1—C3—C4—C9	89.7 (2)	O1—C2—N1—C10	2.4 (3)
C9—C4—C5—C6	−1.1 (3)	C1—C2—N1—C10	−177.1 (2)
C3—C4—C5—C6	175.3 (2)	O1—C2—N1—C3	175.7 (2)
C4—C5—C6—C7	−0.8 (3)	C1—C2—N1—C3	−3.9 (3)
C5—C6—C7—C8	1.6 (4)	C11—C10—N1—C2	52.6 (3)
C5—C6—C7—Br1	−179.47 (17)	C15—C10—N1—C2	−127.1 (2)
C6—C7—C8—C9	−0.5 (4)	C11—C10—N1—C3	−120.6 (2)
Br1—C7—C8—C9	−179.4 (2)	C15—C10—N1—C3	59.7 (3)
C7—C8—C9—C4	−1.5 (4)	C4—C3—N1—C2	−105.3 (2)
C5—C4—C9—C8	2.2 (4)	S1—C3—N1—C2	17.6 (2)
C3—C4—C9—C8	−174.2 (2)	C4—C3—N1—C10	68.2 (3)
C15—C10—C11—C12	0.1 (3)	S1—C3—N1—C10	−168.91 (15)
N1—C10—C11—C12	−179.6 (2)	C2—C1—S1—C3	18.91 (19)
C10—C11—C12—C13	1.0 (3)	N1—C3—S1—C1	−20.26 (17)
C11—C12—C13—O2	179.1 (2)	C4—C3—S1—C1	103.83 (18)
C11—C12—C13—C14	−1.6 (4)

Cg2 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.94	2.758 (2)	175
C5—H5···O2ⁱⁱ	0.93	2.53	3.361 (3)	149
C12—H12···Br1ⁱⁱⁱ	0.93	2.84	3.463 (2)	125
C15—H15···Cg2^iv	0.93	2.94	3.775 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.94	2.758 (2)	175
C5—H5⋯O2ⁱⁱ	0.93	2.53	3.361 (3)	149
C12—H12⋯Br1ⁱⁱⁱ	0.93	2.84	3.463 (2)	125
C15—H15⋯Cg2^iv	0.93	2.94	3.775 (2)	150

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

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