Home The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
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The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S

  • Haiyan Yu ORCID logo and Meng Wang EMAIL logo
Published/Copyright: December 14, 2021

Abstract

C12H11ClN2O3S, monoclinic, P21/n (no. 14), a = 4.7305(8) Å, b = 21.252(4) Å, c = 13.134(2) Å, β = 96.286(2)°, Z = 4, V = 1312.5(4) Å3, R gt (F) = 0.1002, wR ref (F 2) = 0.1118, T = 296 K.

CCDC no.: 2125844

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: Block, yellow
Size: 0.23 × 0.18 × 0.16 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.46 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω-scans
θ max, completeness: 26.4°, >99%
N(hkl)measuredN(hkl)uniqueR int: 7324, 2659, 0.041
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1745
N(param)refined: 222
Programs: Bruker programs [1], OLEX2 [2], SHELX [3]
Table 2:

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

x y z U iso*/U eq
Cl1 0.4677 (2) 0.41023 (5) 0.07264 (7) 0.0794 (3)
S1a −0.5774 (5) 0.18023 (13) 0.17528 (12) 0.0359 (5)
S1Ab −0.5741 (13) 0.1350 (2) 0.3732 (5) 0.0447 (10)
O1 −0.1764 (4) 0.23982 (9) 0.43652 (13) 0.0423 (5)
O2 0.3735 (5) 0.38140 (11) 0.45479 (15) 0.0622 (6)
H2 0.257828 0.354991 0.431318 0.093*
N1 −0.1034 (4) 0.26832 (9) 0.27581 (16) 0.0313 (5)
H1 −0.143715 0.262513 0.211040 0.038*
N2 0.0920 (4) 0.31340 (9) 0.31192 (16) 0.0326 (5)
C1a −0.8024 (13) 0.1201 (3) 0.2042 (5) 0.0337 (13)
H1Aa −0.930103 0.100100 0.155902 0.040*
C2a −0.7712 (15) 0.1056 (4) 0.3049 (4) 0.0366 (13)
H2Aa −0.872661 0.074147 0.333992 0.044*
C3a −0.560 (3) 0.1452 (5) 0.3620 (10) 0.0389 (16)
H3a −0.511765 0.142273 0.432393 0.047*
C4a −0.442 (3) 0.1868 (7) 0.3015 (8) 0.0268 (11)
C5 −0.2301 (5) 0.23355 (11) 0.3434 (2) 0.0284 (6)
C6 0.2079 (5) 0.34486 (12) 0.2449 (2) 0.0336 (6)
H6 0.157538 0.336658 0.175699 0.040*
C7 0.4170 (5) 0.39317 (11) 0.2748 (2) 0.0330 (6)
C8 0.5518 (6) 0.42630 (12) 0.2020 (2) 0.0397 (7)
C9 0.7537 (6) 0.47199 (13) 0.2278 (3) 0.0498 (8)
H9 0.842199 0.492646 0.177544 0.060*
C10 0.8213 (6) 0.48633 (14) 0.3294 (3) 0.0602 (10)
H10 0.956530 0.517172 0.348116 0.072*
C11 0.6925 (7) 0.45590 (15) 0.4034 (3) 0.0585 (9)
H11 0.739815 0.466481 0.471841 0.070*
C12 0.4919 (6) 0.40935 (13) 0.3775 (2) 0.0425 (7)
O3 −0.1429 (4) 0.26026 (11) 0.05977 (13) 0.0520 (6)
H3B −0.012476 0.256708 0.020446 0.078*
H3C −0.296377 0.260587 0.019542 0.078*
C4Ab −0.438 (6) 0.1887 (12) 0.2979 (14) 0.031 (2)
C1Ab −0.790 (3) 0.1057 (6) 0.2723 (8) 0.037 (2)
H1AAb −0.914296 0.072253 0.277537 0.044*
C2Ab −0.761 (2) 0.1356 (5) 0.1846 (9) 0.0316 (18)
H2AAb −0.862352 0.126485 0.121661 0.038*
C3Ab −0.559 (4) 0.1821 (9) 0.2017 (10) 0.033 (2)
H3Ab −0.508760 0.207596 0.149013 0.039*
  1. aOccupancy: 0.642 (3), bOccupancy: 0.358 (3).

Source of materials

A mixture of thiophene-2-carbohydrazide (142.2 mg, 1 mmol) and 2-chloro-6-hydroxybenzaldehyde (156.6 mg, 1 mmol) was dissolved in 20 mL ethanol. A catalytic amount of glacial acetic acid was added and used as catalyst. The reaction mixture was refluxed for 5 h, then cooled to room temperature and filtered, and then left at room temperature quietly. After a few days, light yellow block crystals were obtained.

Experimental details

All hydrogen atoms were positioned geometrically, with C–H = 0.93 Å, N–H = 0.86 Å and O–H = 0.82–0.85 Å. The thiophene ring is disordered over two positions. The two parts were disordered over opposite direction and overlapped each other with site occupation factors of 0.642 and 0.358. The disorder is omitted in the figure for clarity.

Comment

Some thiophene-based Schiff bases have attracted attention due to their biological activities such as antioxidant, antitumor, anti-inflammatory, antimicrobial activities and structural chemistry [4], [5], [6], [7], [8], [9], [10], [11], [12]. In order to synthesize new thiophene-based Schiff bases, the title compound was synthesized and its crystal structure determined and reported here.

The asymmetric unit of the title compound consists of one formula unit (cf. the figure). The bond length between C6 and N2 is 1.277(3) Å, indicating that the reaction of Schiff base has taken place, and the C=N bond was also formed. The dihedral angle between the thiophene and benzene rings is 12.154(1)° in the major component. Due to the consequence of repulsion between the nitrogen lone pairs and the adjacent N bonds, the angle of C6=N2–N1 is 116.7(2)°. Geometric parameters are in the expected ranges [6], [7], [8], [9], [10, 13]. In the crystal packing, the molecules are linked into one-dimensional chains along the b-axis by O–H⃛O hydrogen bonds. In addition, intramolecular O–H⃛N and N–H⃛O hydrogen bonds further consolidate the crystal structure.


Corresponding author: Meng Wang, Department of Pharmacy, The Fourth Hospital of Shijiazhuang, Shijiazhuang Obstetrics and Gynecology Hospital, 050000, Shijiazhuang, Hebei, People’s Republic of China, E-mail:

  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 Nanyang Institute of Technology for financial assistances.

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

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Received: 2021-10-20
Accepted: 2021-12-02
Published Online: 2021-12-14
Published in Print: 2022-02-23

© 2021 Haiyan Yu and Meng Wang, published by De Gruyter, Berlin/Boston

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

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