Home Crystal structure of (E)-N-(1-((2-chlorothiazol-5-yl)methyl)pyridin-2(1H)-ylidene)-2,2,2-trifluoroacetamide, C11H7ClF3N3OS
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Crystal structure of (E)-N-(1-((2-chlorothiazol-5-yl)methyl)pyridin-2(1H)-ylidene)-2,2,2-trifluoroacetamide, C11H7ClF3N3OS

  • Benbo Zhao , Changchun Yuan ORCID logo , Miao-Miao Xun and Kai Fu ORCID logo EMAIL logo
Published/Copyright: April 12, 2021

Abstract

C11H7ClF3N3OS, monoclinic, C2/c (no. 15), a = 21.9623(8) Å, b = 9.7431(4) Å, c = 16.1379(5) Å, β = 132.0530(10)°, V = 2564.09(16) Å3, Z = 8, Rgt(F) = 0.0456, wRref(F2) = 0.0938, T = 170 K.

CCDC no.: 2074204

The molecular structure is shown in Figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless block
Size:0.15 × 0.08 × 0.04 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.50 mm−1
Diffractometer, scan mode:D8 VENTURE, φ and ω
θmax, completeness:26.4°, 99%
N(hkl)measured, N(hkl)unique, Rint:10,808, 2595, 0.043
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2086
N(param)refined:208
Programs:SHELX [1], OLEX2 [2], Bruker [3]
Table 2:

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

AtomxyzUiso*/Ueq
C10.22247 (15)0.4138 (3)0.4289 (2)0.0214 (5)
C20.26719 (16)0.4408 (3)0.5386 (2)0.0272 (6)
H20.2420190.4704570.5656160.033*
C30.36805 (15)0.3836 (3)0.5507 (2)0.0235 (6)
C40.13150 (15)0.4248 (3)0.3374 (2)0.0233 (6)
H4A0.1099410.3404060.2914730.028*
H4B0.1063930.4330340.3701880.028*
C50.10459 (14)0.5335 (3)0.17727 (19)0.0206 (5)
C60.08446 (15)0.6528 (3)0.1143 (2)0.0246 (6)
H60.0791110.6484210.0508660.030*
C70.07250 (16)0.7750 (3)0.1433 (2)0.0289 (6)
H70.0596710.8548710.1005170.035*
C80.07896 (16)0.7833 (3)0.2355 (2)0.0307(6)
H80.0713190.8682090.2564240.037*
C90.09641 (15)0.6673 (3)0.2941 (2)0.0264 (6)
H90.1003010.6708310.3563520.032*
C100.12355 (14)0.3789 (3)0.0854 (2)0.0233 (6)
C110.15125 (16)0.2306 (3)0.0948 (2)0.0295 (6)
Cl10.46704 (4)0.35439 (8)0.60903 (5)0.03268 (19)
F1a0.1403 (5)0.1459 (10)0.1448 (7)0.073 (2)
F2a0.1083 (4)0.1381 (9)0.1011 (6)0.0483 (17)
F3a0.1166 (6)0.1793 (14)−0.0032 (8)0.057 (3)
F4a0.1399 (6)0.1900 (14)0.0074 (7)0.060 (3)
F5a0.2306 (7)0.2290 (16)0.1533 (9)0.084 (4)
F6a0.2278 (6)0.2086 (13)0.1815 (8)0.064 (3)
N10.35073 (13)0.4232 (2)0.60898 (17)0.0277 (5)
N20.12358 (12)0.4066 (2)0.16625 (17)0.0229 (5)
N30.10845 (12)0.5459 (2)0.26552 (16)0.0210 (5)
O10.10764 (12)0.4476 (2)0.00912 (16)0.0336 (5)
S10.28745 (4)0.36320 (7)0.40916 (5)0.02350 (17)
  1. aOccupancy: 0.5.

Source of material

The title compound was prepared according to a known procedure in two steps with commercially available 2-chloro-5-(chloromethyl)thiazole and 2-aminopyridine as starting materials affording the product as a white solid [4]. The crude product was recrystallized from ethyl acetate as crystals suitable for X-ray diffraction analysis.

Experimental details

All H atoms were positioned geometrically and treated as riding, with C–H bond lengths constrained to 0.99 Å for ethyl H atoms, 0.95 Å for alkenyl H atoms, and with Uiso(H) = 1.2 Ueq(C) for ethyl H atoms, and alkenyl H atoms.

Comment

The title N-pyridyltrifluoroacetamide derivative chemically named as (E)-N-(1-((2-chlorothiazol-5-yl)methyl)pyridin-2(1H)-ylidene)-2,2,2-trifluoroacetamide has been proven to be one of the useful pest control agents [4]. Here we report the crystal structure of the title compound. In the crystal structure, the crystal packing is stabilized and held together by van der Waals forces. Bond lengths and angles are all in the expected ranges [5].


Corresponding author: Kai Fu, School of Chemical Engineering and Technology, North University of China, Taiyuan, Shanxi Province, P. R. China; and Dezhou Graduate School of North University of China, Dezhou, Shandong Province, P. R. China, E-mail:

Funding source: Applied Basic Research Programs of Shanxi Province of China

Award Identifier / Grant number: 201901D211220

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by the Applied Basic Research Programs of Shanxi Province of China (Grant No. 201901D211220).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341.10.1107/S0021889808042726Search in Google Scholar

3. BRUKER. SAINT, APEX2 and SADABS. Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Search in Google Scholar

4. Nakanishi, N., Fukuda, Y., Kitsuda, S., Ohno, I. Method for the Preparation of Pest Controlling Agent. Patent WO 2013031671.Search in Google Scholar

Received: 2021-03-12
Accepted: 2021-03-30
Published Online: 2021-04-12
Published in Print: 2021-07-27

© 2021 Benbo Zhao et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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