Home The crystal structure of N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3-(2-methylphenyl)-2-sulfanylprop-2-enamide hydrate, C19H17BrN2O2S2
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The crystal structure of N-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-3-(2-methylphenyl)-2-sulfanylprop-2-enamide hydrate, C19H17BrN2O2S2

  • Lei-Qiang Ni , Xiao-Meng Guo , Ze-Lin Wang and Juan Sun ORCID logo EMAIL logo
Published/Copyright: February 28, 2024

Abstract

C19H17BrN2O2S2, triclinic, P 1 (no. 2), a = 7.8069(5) Å, b = 8.0787(5) Å, c = 15.7738(9) Å, α = 97.540(2)°, β = 90.179(2)°, γ = 104.507(2)°, V = 954.13(10) Å3, Z = 2, R gt(F) = 0.0423, wR ref(F 2) = 0.1134, T = 296.15 K.

CCDC no.: 2332892

The molecular structure is shown in the 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: 0.42 × 0.23 × 0.16 mm
Wavelength: Mo radiation (0.71073 Å)
μ: 2.39 mm−1
Diffractometer, scan mode: Bruker D8 venture
θ max, completeness: 28.3°, >99 %
N(hkl)measured, N(hkl)unique, R int: 10,730, 4580, 0.023
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3316
N(param)refined: 243
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 −0.02511 (4) 0.96692 (5) 0.79994 (2) 0.06904 (15)
C1 0.1478 (4) 0.9205 (3) 0.72251 (17) 0.0417 (6)
C2 0.1010 (4) 0.7847 (4) 0.65776 (18) 0.0450 (6)
H2A −0.013885 0.714451 0.652199 0.054*
C3 0.2281 (4) 0.7539 (3) 0.60076 (17) 0.0413 (6)
H3 0.196943 0.663010 0.556299 0.050*
C4 0.4007 (3) 0.8561 (3) 0.60869 (15) 0.0352 (5)
C5 0.4430 (4) 0.9936 (3) 0.67508 (17) 0.0417 (6)
H5 0.557471 1.064629 0.680932 0.050*
C6 0.3177 (4) 1.0260 (4) 0.73230 (17) 0.0441 (6)
H6 0.347368 1.117241 0.776650 0.053*
C7 0.5354 (3) 0.8191 (3) 0.54920 (15) 0.0374 (5)
C8 0.7131 (4) 0.8799 (4) 0.55991 (18) 0.0512 (7)
H8 0.769974 0.954474 0.607300 0.061*
C9 0.6162 (3) 0.6900 (3) 0.42989 (15) 0.0351 (5)
C10 0.7262 (3) 0.5710 (3) 0.29823 (16) 0.0363 (5)
C11 0.6742 (3) 0.4646 (3) 0.21356 (16) 0.0372 (5)
C12 0.7777 (4) 0.4894 (4) 0.14743 (17) 0.0443 (6)
H12A 0.891071 0.475775 0.166437 0.053*
H12B 0.796375 0.610717 0.141849 0.053*
C13 0.7479 (4) 0.3989 (4) 0.05943 (17) 0.0444 (6)
C14 0.7112 (4) 0.2203 (4) 0.0438 (2) 0.0585 (8)
H14 0.701224 0.157185 0.089614 0.070*
C15 0.6892 (5) 0.1347 (5) −0.0388 (2) 0.0687 (10)
H15 0.665674 0.014990 −0.048562 0.082*
C16 0.7024 (4) 0.2274 (5) −0.1062 (2) 0.0657 (9)
H16 0.687110 0.170511 −0.161945 0.079*
C17 0.7378 (4) 0.4026 (5) −0.09179 (19) 0.0602 (8)
H17 0.746490 0.463760 −0.138262 0.072*
C18 0.7614 (4) 0.4927 (4) −0.00933 (18) 0.0476 (7)
C19 0.7960 (6) 0.6869 (4) 0.0052 (2) 0.0693 (9)
H19A 0.703065 0.719013 0.037934 0.104*
H19B 0.799404 0.729418 −0.048987 0.104*
H19C 0.907392 0.735692 0.035845 0.104*
N1 0.4802 (3) 0.7088 (3) 0.47415 (13) 0.0367 (5)
N2 0.5933 (3) 0.5875 (3) 0.35109 (14) 0.0388 (5)
O1 0.8801 (2) 0.6447 (3) 0.31849 (12) 0.0490 (5)
O2 1.2286 (3) 0.6042 (4) 0.33132 (18) 0.0836 (8)
H2B 1.255186 0.648689 0.383035 0.125*
H2C 1.121844 0.608014 0.323791 0.125*
S1 0.82041 (9) 0.80169 (11) 0.47489 (5) 0.0516 (2)
S2 0.46879 (10) 0.31741 (10) 0.20506 (5) 0.04803 (19)
H2 0.490 (4) 0.544 (4) 0.3335 (19) 0.045 (8)*

1 Source of materials

2-(4-Bromophenyl)-4-thiazolamine (0.25 g, 1 mmol) and 2-mercapto-3-(2-methylphenyl)-2-propenoic acid (0.19 g, 1 mmol) were mixed in dichloromethane (20 mL) and stirred for 10 h under the catalytic of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.095 g, 0.5 mmol) and 1-hydroxybenzotriazole monohydrate (0.0068 g, 0.05 mmol). After filtration and drying, the title compound was obtained. Then, 5 mg of the title compound was dissolved in 5 mL of ethanol, and the solution was kept at room temperature for three days. Colourless block-shaped single crystals were obtained by slow evaporation.

2 Experimental details

Absorption corrections were applied by using multi-scan program [1]. Using Olex2 [2], the structure was solved with the ShelXT [3] structure solution program using intrinsic phasing and refined with the ShelXT [4] refinement package using least squares minimisation.

3 Comment

Researchers have long shown a keen interest in heterocyclic compounds that incorporate sulphur and nitrogen atoms [56]. In the crystal structure of the title compound, the asymmetric unit consists of one formula unit of the title molecule and one water molecule. This compound’s structure is novel and has been reported for the first time. The dihedral angle between the bromine-substituted benzene ring and the thiazole ring is 15.42°. Similarly, the dihedral angle between the methyl-substituted benzene ring and the thiazole ring is 79.58°. Furthermore, the dihedral angle between these two benzene rings is 69.05°. There is intramolecular hydrogen bond N2–H2⃛S2 in the molecule. In the crystal phase, molecules are bound by intermolecular hydrogen bonds N2–H2⃛O2, O2–H2C⃛O1 and O2–H2b⃛N1. The single-crystal structure analysis confirms that all bond lengths and bond angles of the compound fall within a reasonable range.


Corresponding author: Juan Sun, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou, Liuhe Road 318#, China, E-mail:

Funding source: National Undergraduate Training Programs for Innovation and Entrepreneurship

Award Identifier / Grant number: 202211057022

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

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

  3. Research funding: This work was supported by National Undergraduate Training Programs for Innovation and Entrepreneurship (202211057022).

References

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Received: 2024-01-09
Accepted: 2024-02-14
Published Online: 2024-02-28
Published in Print: 2024-06-25

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

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