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BY 4.0 license Open Access Published by De Gruyter (O) January 26, 2022

Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S

Cui-Cui Li and Li Zhang ORCID logo

Abstract

C13H11ClN2O2S, orthorhombic, Pna21/n (no. 33), a = 33.781(4) Å, b = 5.2087(6) Å, c = 7.2979(8) Å, β = 90°, V = 1284.1(3) Å3, Z = 4, R gt (F) = 0.0429, wR ref (F2) = 0.1267, T = 296 K.

CCDC no.: 2141830

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: Yellow block
Size: 0.23 × 0.20 × 0.18 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.46 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint: 6160, 2235, 0.036
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1794
N(param)refined: 175
Programs: Bruker [1], SHELX [2]

Table 2:

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

Atom x y Z Uiso*/Ueq
C1 0.9810 (2) 0.8480 (12) −0.2536 (10) 0.0548 (19)
H1 0.999426 0.835520 −0.347966 0.066*
C2 0.95310 (19) 1.0332 (12) −0.2452 (9) 0.0493 (17)
H2 0.950049 1.158192 −0.335087 0.059*
C3 0.92900 (15) 1.0200 (10) −0.0878 (8) 0.0317 (12)
H3 0.908686 1.133749 −0.059482 0.038*
C4 0.94041 (15) 0.8075 (10) 0.0204 (8) 0.0352 (13)
C5 0.92251 (16) 0.7127 (11) 0.1901 (8) 0.0363 (13)
C6 0.85330 (16) 0.9566 (10) 0.5007 (8) 0.0329 (12)
C7 0.83529 (17) 1.1750 (12) 0.3945 (9) 0.0453 (16)
H7A 0.851286 1.325874 0.409198 0.068*
H7B 0.809073 1.208206 0.439383 0.068*
H7C 0.834009 1.130062 0.267014 0.068*
C8 0.83714 (16) 0.8753 (11) 0.6793 (8) 0.0313 (13)
C9 0.85195 (17) 0.6599 (11) 0.7735 (8) 0.0363 (13)
C10 0.83517 (18) 0.5908 (11) 0.9432 (9) 0.0436 (15)
H10 0.845315 0.450029 1.005952 0.052*
C11 0.80461 (18) 0.7239 (12) 1.0179 (9) 0.0440 (14)
H11 0.793521 0.673025 1.128706 0.053*
C12 0.79030 (15) 0.9362 (10) 0.9260 (9) 0.0368 (13)
C13 0.80551 (16) 1.0129 (11) 0.7604 (8) 0.0340 (13)
H13 0.795003 1.155584 0.701210 0.041*
Cl1 0.75141 (5) 1.1113 (3) 1.0210 (3) 0.0548 (5)
N1 0.90097 (14) 0.8956 (9) 0.2811 (7) 0.0406 (12)
H1A 0.898602 1.048873 0.238615 0.049*
N2 0.88332 (13) 0.8246 (8) 0.4430 (7) 0.0369 (11)
O1 0.92519 (13) 0.4914 (9) 0.2437 (6) 0.0507 (12)
O2 0.88196 (13) 0.5141 (8) 0.7116 (6) 0.0451 (11)
H2A 0.888517 0.563296 0.609249 0.068*
S1 0.97918 (5) 0.6426 (3) −0.0765 (3) 0.0503 (5)

Source of material

A mixture of thiophene-2-carbohydrazide (142.2 mg, 1 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (170.6 mg, 1 mmol) was dissolved in 25 mL anhydrous ethanol containing a catalytic amount of glacial acetic acid. The reaction mixture was stirred under reflux for 3 h, then cooled to room temperature and filtered, and then left at room temperature. After six days, yellow block crystals were obtained.

Experimental details

All hydrogen atoms were positioned geometrically (C–H = 0.93–0.96 Å, O–H = 0.82 Å, N–H = 0.86 Å) and refined using a riding model approximation. The U iso values were constrained to be 1.5 U eq of the carrier atom for oxygen atom and methyl groups and 1.2 U eq for the remaining H atoms.

Comment

Thiophene hydrazone schiff bases are attracting more and more attention due to their biological activities and wide applications in coordination chemistry [3], [4], [5], [6], [7], [8], [9], [10].

The asymmetric unit of the title compound consists of one molecule of the organic target compound (see the figure). The title compound shows an E configuration around the C6=N2 bond. In the crystal structure, the short distance d(C6–N2) = 1.296(7) Å shows a typical C=N double bond. The angle of C6=N2–N1 is 118.4(5)°. In general the bond lengths and angles are as expected [11, 12]. The thiophene and the 5-chloro-2-hydroxyphenyl ring are almost parallel, with the dihedral angle of 1.6°. In the crystal structure, the molecules are linked into chains along the b-axis by O–H⃛N and C–H⃛O hydrogen bonds. One intramolecular N–H⃛O hydrogen bond exists, which stabilizes the conformation of the title molecule (see the figure).


Corresponding author: Li Zhang, Changchun Oubang Biotechnology Co., Ltd., 130000, Changchun, Jilin, People’s Republic of China, E-mail:

Funding source: Nanyang Institute of Technology

  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 financial supported by Nanyang Institute of Technology.

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

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Received: 2021-12-01
Accepted: 2022-01-13
Published Online: 2022-01-26
Published in Print: 2022-04-26

© 2022 Cui-Cui Li and Li Zhang, published by De Gruyter, Berlin/Boston

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