Literature DB >> 21201202

Ethyl 2-phenyl-5-trifluoro-methyl-1,3-thia-zole-4-carboxyl-ate.

Hai-Zhen Jiang, Wen Wan, Min Shao, Jian Hao.

Abstract

In the title compound, C(13)H(10)F(3)NO(2)S, the dihedral angle between the thia-zole and phenyl rings is 5.15 (1)°. No inter-molecular hydrogen bonding is observed in the crystal structure.

Entities: CellLine Chemical Disease Gene

Year: 2008 PMID： 21201202 PMCID： PMC2959226 DOI： 10.1107/S1600536808030389

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

Related literature

For general backgroud, see: Sasse et al. (2002 ▶); Campeau et al. (2008 ▶); Zificsak & Hlasta (2004 ▶); Rynbrandt et al. (1981 ▶). For a related structure, see: Kennedy et al. (2004 ▶).

Experimental

Crystal data

C13H10F3NO2S M = 301.28 Monoclinic, a = 8.930 (3) Å b = 21.232 (6) Å c = 7.574 (2) Å β = 110.861 (4)° V = 1342.0 (7) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 296 (2) K 0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.922, T max = 0.973 6891 measured reflections 2367 independent reflections 1417 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.142 S = 1.01 2367 reflections 182 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030389/xu2454sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030389/xu2454Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₃H₁₀F₃NO₂S	F(000) = 616
M_r = 301.28	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 320 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.930 (3) Å	Cell parameters from 1005 reflections
b = 21.232 (6) Å	θ = 2.5–19.0°
c = 7.574 (2) Å	µ = 0.28 mm⁻¹
β = 110.861 (4)°	T = 296 K
V = 1342.0 (7) Å³	Needle, colorless
Z = 4	0.30 × 0.10 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	2367 independent reflections
Radiation source: fine-focus sealed tube	1417 reflections with I > 2σ(I)
graphite	R_int = 0.050
φ and ω scans	θ_max = 25.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.922, T_max = 0.973	k = −25→19
6891 measured reflections	l = −8→8

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0642P)²] where P = (F_o² + 2F_c²)/3
2367 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Experimental. IR (KBr, cm^-1): 3061, 2980, 1737, 1633, 1513, 1461, 1290, 1210, 766, 689. ¹H NMR (CDCl₃, 500 MHz). δ/p.p.m.: 7.46–8.00 (m, 5H), 4.49 (q, J = 7.0 Hz, 2H), 1.44 (t, J = 7.0 Hz, 3H). ¹³C NMR (CDCl₃, 125 MHz). δ/p.p.m.: 168.87, 160.27, 146.48, 131.77, 131.63, 129.24, 164.15 (q, ²J_C—F = 36.5 Hz, CF₃C–), 123.33 (q, ¹J_C—F = 269.3 Hz, –CF₃), 62.41, 13.98. ¹⁹F NMR (CDCl₃, 470 MHz, CFCl₃). δ/p.p.m.: -52.44 (s).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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	0.22302 (11)	0.67958 (4)	0.44789 (13)	0.0585 (3)
C1	0.1690 (4)	0.75511 (15)	0.3693 (5)	0.0504 (8)
C2	0.2697 (4)	0.80979 (15)	0.4545 (5)	0.0523 (8)
C3	0.4186 (4)	0.80233 (17)	0.5954 (5)	0.0615 (10)
H3	0.4559	0.7622	0.6376	0.074*
C4	0.5115 (4)	0.85408 (19)	0.6732 (5)	0.0681 (10)
H4	0.6116	0.8488	0.7671	0.082*
C5	0.4564 (5)	0.91329 (18)	0.6123 (6)	0.0720 (11)
H5	0.5192	0.9483	0.6646	0.086*
C6	0.3083 (5)	0.92108 (18)	0.4743 (6)	0.0741 (11)
H6	0.2708	0.9614	0.4343	0.089*
C7	0.2154 (4)	0.86972 (16)	0.3947 (5)	0.0642 (10)
H7	0.1156	0.8753	0.3004	0.077*
C8	−0.0328 (4)	0.70143 (16)	0.1739 (5)	0.0514 (8)
C9	0.0515 (4)	0.65213 (16)	0.2791 (5)	0.0517 (8)
C10	0.0138 (5)	0.58379 (17)	0.2771 (6)	0.0674 (10)
C11	−0.1837 (4)	0.69976 (18)	0.0062 (5)	0.0577 (9)
C12	−0.3482 (5)	0.63721 (19)	−0.2455 (6)	0.0857 (13)
H12A	−0.3442	0.6683	−0.3375	0.103*
H12B	−0.4455	0.6438	−0.2188	0.103*
C13	−0.3463 (7)	0.5732 (2)	−0.3197 (7)	0.133 (2)
H13A	−0.2565	0.5689	−0.3603	0.200*
H13B	−0.4438	0.5660	−0.4249	0.200*
H13C	−0.3375	0.5429	−0.2224	0.200*
F1	−0.1303 (3)	0.57367 (10)	0.2825 (4)	0.0973 (8)
F2	0.0198 (3)	0.55287 (10)	0.1294 (4)	0.0932 (8)
F3	0.1174 (3)	0.55518 (10)	0.4280 (4)	0.1071 (9)
N1	0.0337 (3)	0.75955 (12)	0.2277 (4)	0.0522 (7)
O1	−0.2677 (3)	0.74436 (12)	−0.0528 (4)	0.0791 (8)
O2	−0.2081 (3)	0.64335 (11)	−0.0726 (3)	0.0693 (7)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0601 (6)	0.0546 (6)	0.0597 (6)	0.0055 (4)	0.0201 (5)	0.0032 (4)
C1	0.053 (2)	0.054 (2)	0.053 (2)	0.0023 (16)	0.0291 (19)	0.0011 (16)
C2	0.058 (2)	0.055 (2)	0.049 (2)	0.0007 (17)	0.0249 (18)	−0.0021 (17)
C3	0.060 (2)	0.057 (2)	0.069 (3)	0.0017 (18)	0.024 (2)	0.0034 (18)
C4	0.058 (2)	0.075 (3)	0.066 (3)	−0.007 (2)	0.016 (2)	−0.003 (2)
C5	0.074 (3)	0.058 (3)	0.086 (3)	−0.010 (2)	0.030 (2)	−0.010 (2)
C6	0.073 (3)	0.057 (2)	0.089 (3)	0.004 (2)	0.024 (2)	−0.005 (2)
C7	0.063 (2)	0.054 (2)	0.070 (3)	0.0019 (18)	0.015 (2)	−0.0032 (18)
C8	0.053 (2)	0.049 (2)	0.057 (2)	0.0039 (16)	0.0256 (19)	−0.0011 (17)
C9	0.0499 (19)	0.054 (2)	0.057 (2)	0.0036 (16)	0.0259 (17)	−0.0019 (17)
C10	0.070 (3)	0.054 (2)	0.076 (3)	0.0024 (19)	0.022 (2)	0.003 (2)
C11	0.056 (2)	0.056 (2)	0.063 (2)	0.0018 (18)	0.023 (2)	0.0041 (19)
C12	0.084 (3)	0.079 (3)	0.073 (3)	−0.004 (2)	0.003 (2)	−0.001 (2)
C13	0.172 (5)	0.076 (4)	0.103 (4)	0.002 (3)	−0.012 (4)	−0.012 (3)
F1	0.0903 (17)	0.0681 (15)	0.149 (2)	−0.0148 (12)	0.0613 (17)	0.0074 (14)
F2	0.118 (2)	0.0605 (14)	0.109 (2)	0.0018 (12)	0.0492 (16)	−0.0211 (13)
F3	0.123 (2)	0.0591 (15)	0.108 (2)	0.0033 (13)	0.0028 (17)	0.0185 (13)
N1	0.0500 (18)	0.0519 (18)	0.0575 (18)	0.0012 (13)	0.0227 (16)	0.0024 (13)
O1	0.0707 (18)	0.0663 (18)	0.083 (2)	0.0126 (14)	0.0060 (15)	0.0000 (14)
O2	0.0701 (16)	0.0554 (16)	0.0701 (18)	−0.0010 (12)	0.0100 (14)	−0.0024 (13)

S1—C9	1.710 (3)	C8—C9	1.367 (4)
S1—C1	1.719 (3)	C8—C11	1.487 (5)
C1—N1	1.302 (4)	C9—C10	1.489 (5)
C1—C2	1.470 (5)	C10—F2	1.315 (4)
C2—C7	1.380 (4)	C10—F1	1.319 (4)
C2—C3	1.386 (5)	C10—F3	1.334 (4)
C3—C4	1.376 (5)	C11—O1	1.192 (4)
C3—H3	0.9300	C11—O2	1.321 (4)
C4—C5	1.369 (5)	C12—O2	1.459 (4)
C4—H4	0.9300	C12—C13	1.474 (5)
C5—C6	1.373 (5)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—C7	1.373 (5)	C13—H13A	0.9600
C6—H6	0.9300	C13—H13B	0.9600
C7—H7	0.9300	C13—H13C	0.9600
C8—N1	1.367 (4)

C9—S1—C1	89.59 (17)	C8—C9—S1	109.6 (3)
N1—C1—C2	123.2 (3)	C10—C9—S1	118.6 (3)
N1—C1—S1	114.6 (2)	F2—C10—F1	106.3 (3)
C2—C1—S1	122.2 (3)	F2—C10—F3	106.0 (3)
C7—C2—C3	119.1 (3)	F1—C10—F3	106.6 (3)
C7—C2—C1	119.7 (3)	F2—C10—C9	114.7 (3)
C3—C2—C1	121.1 (3)	F1—C10—C9	112.2 (3)
C4—C3—C2	120.3 (3)	F3—C10—C9	110.5 (3)
C4—C3—H3	119.8	O1—C11—O2	124.8 (4)
C2—C3—H3	119.8	O1—C11—C8	124.0 (3)
C5—C4—C3	120.0 (4)	O2—C11—C8	111.2 (3)
C5—C4—H4	120.0	O2—C12—C13	107.6 (4)
C3—C4—H4	120.0	O2—C12—H12A	110.2
C4—C5—C6	120.0 (4)	C13—C12—H12A	110.2
C4—C5—H5	120.0	O2—C12—H12B	110.2
C6—C5—H5	120.0	C13—C12—H12B	110.2
C5—C6—C7	120.4 (4)	H12A—C12—H12B	108.5
C5—C6—H6	119.8	C12—C13—H13A	109.5
C7—C6—H6	119.8	C12—C13—H13B	109.5
C6—C7—C2	120.1 (4)	H13A—C13—H13B	109.5
C6—C7—H7	119.9	C12—C13—H13C	109.5
C2—C7—H7	119.9	H13A—C13—H13C	109.5
N1—C8—C9	115.3 (3)	H13B—C13—H13C	109.5
N1—C8—C11	116.2 (3)	C1—N1—C8	110.9 (3)
C9—C8—C11	128.5 (3)	C11—O2—C12	115.9 (3)
C8—C9—C10	131.6 (3)

4 in total

1. Argyrins, immunosuppressive cyclic peptides from myxobacteria. I. Production, isolation, physico-chemical and biological properties.

Authors: Florenz Sasse; Heinrich Steinmetz; Thomas Schupp; Frank Petersen; Klaus Memmert; Hans Hofmann; Christoph Heusser; Volker Brinkmann; Peter von Matt; Gerhard Höfle; Hans Reichenbach
Journal: J Antibiot (Tokyo) Date: 2002-06 Impact factor: 2.649