Home The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
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The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3

  • Guo-Xiang Sun ORCID logo EMAIL logo , Li-Jing Min , Liang Han and Xing-Hai Liu
Published/Copyright: January 4, 2022

Abstract

C13H12ClN3, orthorhombic, Fdd2 (no. 43), a = 28.7760(11) Å, b = 41.7393(17) Å, c = 8.5929(3) Å, V = 10,320.8(7) Å3, Z = 32, R gt (F) = 0.0477, wR ref (F2) = 0.0976, T = 296 K.

CCDC no.: 2127402

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: Colorless block
Size: 0.86 × 0.69 × 0.28 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.28 mm−1
Scan mode: Ω-scans
θmax, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint: 9647, 4032, 0.054
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2155
N(param)refined: 309
Programs: Olex2 [1], SHELX [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
Cl1 0.14907 (5) 0.10676 (4) 0.97745 (18) 0.0832 (6)
N1 0.25519 (17) 0.15579 (12) 1.1510 (6) 0.0668 (13)
N2 0.18239 (14) 0.14320 (11) 1.2509 (5) 0.0653 (13)
H2 0.1559 0.1338 1.2421 0.078*
N3 0.19270 (15) 0.16015 (10) 1.3844 (6) 0.0578 (12)
C1 0.20317 (17) 0.12420 (13) 0.9980 (7) 0.0590 (15)
C2 0.2350 (2) 0.12183 (14) 0.8815 (7) 0.0713 (17)
H2A 0.2279 0.1107 0.7908 0.086*
C3 0.2776 (2) 0.13613 (16) 0.9000 (8) 0.0774 (19)
H3 0.3002 0.1346 0.8231 0.093*
C4 0.2858 (2) 0.15269 (16) 1.0346 (9) 0.0770 (19)
H4 0.3146 0.1625 1.0460 0.092*
C5 0.2140 (2) 0.14132 (13) 1.1326 (7) 0.0565 (15)
C6 0.16139 (18) 0.15986 (13) 1.4911 (7) 0.0580 (15)
H6 0.1343 0.1481 1.4755 0.070*
C7 0.1674 (2) 0.17739 (13) 1.6348 (6) 0.0516 (14)
C8 0.20846 (19) 0.19301 (13) 1.6705 (6) 0.0606 (16)
H8 0.2329 0.1927 1.5997 0.073*
C9 0.2135 (2) 0.20902 (14) 1.8104 (7) 0.0688 (17)
H9 0.2414 0.2193 1.8313 0.083*
C10 0.1786 (2) 0.21023 (14) 1.9196 (7) 0.0689 (18)
C11 0.1843 (2) 0.22825 (17) 2.0705 (7) 0.102 (3)
H11A 0.1744 0.2500 2.0567 0.154*
H11B 0.2164 0.2279 2.1013 0.154*
H11C 0.1657 0.2183 2.1498 0.154*
C12 0.1377 (2) 0.19496 (16) 1.8823 (8) 0.0790 (18)
H12 0.1132 0.1956 1.9529 0.095*
C13 0.1319 (2) 0.17874 (14) 1.7433 (7) 0.0708 (16)
H13 0.1038 0.1686 1.7224 0.085*
Cl2 0.05160 (6) 0.02663 (4) 1.1392 (2) 0.1052 (7)
N4 0.11658 (18) 0.08678 (12) 1.4173 (7) 0.0792 (15)
N5 0.06095 (15) 0.09503 (12) 1.2282 (5) 0.0636 (13)
H5 0.0409 0.0878 1.1630 0.076*
N6 0.06571 (16) 0.12764 (12) 1.2492 (5) 0.0578 (12)
C14 0.0864 (2) 0.04140 (16) 1.2876 (7) 0.0622 (16)
C15 0.1106 (2) 0.02108 (16) 1.3774 (10) 0.089 (2)
H15 0.1084 −0.0010 1.3634 0.107*
C16 0.1392 (3) 0.0341 (2) 1.4923 (10) 0.110 (2)
H16 0.1567 0.0210 1.5575 0.132*
C17 0.1407 (2) 0.0665 (2) 1.5059 (9) 0.093 (2)
H17 0.1599 0.0751 1.5822 0.112*
C18 0.0882 (2) 0.07418 (15) 1.3112 (7) 0.0573 (15)
C19 0.0356 (2) 0.14463 (15) 1.1803 (7) 0.0636 (17)
H19 0.0120 0.1343 1.1257 0.076*
C20 0.0362 (2) 0.17938 (15) 1.1827 (7) 0.0627 (16)
C21 0.0651 (2) 0.19768 (19) 1.2714 (9) 0.088 (2)
H21 0.0856 0.1876 1.3395 0.105*
C22 0.0649 (3) 0.2307 (2) 1.2628 (11) 0.105 (3)
H22 0.0852 0.2425 1.3242 0.127*
C23 0.0345 (4) 0.24642 (19) 1.1632 (11) 0.107 (3)
C24 0.0060 (3) 0.2281 (2) 1.0782 (10) 0.134 (3)
H24 −0.0151 0.2379 1.0111 0.161*
C25 0.0070 (2) 0.1959 (2) 1.0874 (9) 0.108 (3)
H25 −0.0134 0.1842 1.0251 0.129*
C26 0.0362 (4) 0.28315 (18) 1.1560 (12) 0.181 (4)
H26A 0.0330 0.2900 1.0499 0.272*
H26B 0.0654 0.2905 1.1967 0.272*
H26C 0.0113 0.2919 1.2168 0.272*

Source of material

According to our previous work [4], the 3-chloro-2-hydrazinylpyridine and 4-methylbenzaldehyde was stirred in EtOH (50 mL) at room temperature overnight. The obtained solid was, filtered and dried with 75% yield. The solid was recrystallized from ethanol to obtain colorless block crystals.

Experimentaldetails

Coordinates of hydrogen atoms were added using the standard AFIX options of the SHELX system. Their Uiso values were set to 1.2Ueq of the parent atoms. Using Olex2 [1], the structure was refined with the ShelXL [3].

Comment

Some pyridine derivatives possess biological activity, such as herbicidal activity [5], insecticidal activity [6], fungicidal activity [7]. While hydrazone is also a key group in some drugs or pesticides [8].

There are two crystallographically independent molecules in the asymmetric unit of the title structure (see the figure). The bond lengths and bond angles of ring systems (pyridine ring and phenyl ring) are in the normal ranges [9, 10]. The C6=N3 (C19–N6) double bond indicated the E configuration which is according to the normal double bond length [11], and the E configuration is the same as in some reported structures [1214]. The torsion angles of C7–C6–N3–N2 and C6–N3–N2–C5 are −178.3(4)° and −178.1(4)° (2. molecule: C18–N5–N6–C19–172.6(5)° and N5–N6–C19–C20–177.0(5)°).


Corresponding author: Guo-Xiang Sun, School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, 224051, Jiangsu, China, E-mail:

Award Identifier / Grant number: LY19C140002

Award Identifier / Grant number: LY19B020009

Funding source: Chemical Company for Research

Award Identifier / Grant number: KYY-HX-20210140

Award Identifier / Grant number: KYY-HX-20190720

  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 funded by Zhejiang Provincial Natural Science Foundation of China (Nos. LY19C140002, LY19B020009), the Chemical Company for Research (KYY-HX-20210140, KYY-HX-20190720).

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

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Received: 2021-11-08
Accepted: 2021-12-09
Published Online: 2022-01-04
Published in Print: 2022-02-23

© 2021 Guo-Xiang Sun 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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