Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn

Jingjing Qing; Jie Tian; Xin Deng; Fuxing Zhang

doi:10.1515/ncrs-2023-0419

Open Access Published by De Gruyter (O) November 7, 2023

Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C₂₇H₃₉N₃O₂Sn

Jingjing Qing , Jie Tian , Xin Deng and Fuxing Zhang

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2023-0419

Abstract

C₂₇H₃₉N₃O₂Sn, monoclinic, P2₁/c (no. 14), a = 10.3317(6) Å, b = 15.8067(9) Å, c = 16.5497(9) Å, β = 90.5380(10)^°, V = 2702.6(3) Å³, Z = 4, R_gt(F) = 0.0370, wR_ref(F²) = 0.0954, T = 296(2) K.

CCDC no.: 2278991

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:	Colorless lump
Size:	0.20 × 0.19 × 0.18 mm
Wavelength:	MoKα radiation (0.71073 Å)
μ:	0.97 mm⁻¹
Diffractometer, scan mode:	Bruker APEX-II, φ and ω
θ_max, completeness:	26.4°, >99 %
N(hkl)_measured, N(hkl)_unique, R_int:	30,612, 5552, 0.016
Criterion for I_obs, N(hkl)_gt:	I_obs > 2σ(I_obs), 5311
N(param)_refined:	299
Programs:	Bruker [1], Shelx [2, 3], WinGX/Ortep [4]

Table 2:

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

Atom	x	y	z	U_iso*/U_eq
Sn1	0.25939 (2)	0.21054 (2)	0.02219 (2)	0.03203 (9)
C1	0.2663 (3)	0.3468 (2)	0.0329 (2)	0.0447 (8)
H1	0.339761	0.358251	0.069176	0.054*
O1	0.4246 (2)	0.19177 (16)	0.10000 (14)	0.0420 (5)
O2	0.5619 (2)	0.2620 (2)	0.02118 (15)	0.0533 (6)
C2	0.1505 (5)	0.3859 (3)	0.0740 (3)	0.0649 (11)
H2A	0.138742	0.359771	0.126453	0.078*
H2B	0.073205	0.375544	0.041784	0.078*
C6	0.2990 (5)	0.3912 (3)	−0.0452 (3)	0.0669 (12)
H6A	0.232310	0.379055	−0.085154	0.080*
H6B	0.380261	0.369186	−0.065302	0.080*
N1	1.0393 (3)	0.2688 (2)	0.43958 (18)	0.0454 (7)
C7	0.3145 (3)	0.1415 (2)	−0.0837 (2)	0.0432 (7)
H7	0.236560	0.110620	−0.100554	0.052*
C12	0.4159 (5)	0.0737 (3)	−0.0674 (3)	0.0668 (12)
H12A	0.387663	0.037809	−0.023373	0.080*
H12B	0.496730	0.100248	−0.051165	0.080*
C11	0.4378 (7)	0.0198 (3)	−0.1425 (3)	0.0919 (18)
H11A	0.507753	−0.019686	−0.131855	0.110*
H11B	0.360212	−0.012769	−0.153939	0.110*
C10	0.4703 (6)	0.0720 (4)	−0.2148 (3)	0.0951 (19)
H10A	0.554286	0.098135	−0.206533	0.114*
H10B	0.475849	0.035455	−0.261781	0.114*
C9	0.3717 (5)	0.1392 (3)	−0.2306 (3)	0.0723 (13)
H9A	0.290456	0.113014	−0.246415	0.087*
H9B	0.400171	0.174551	−0.274874	0.087*
C8	0.3506 (4)	0.1943 (3)	−0.1553 (2)	0.0535 (9)
H8A	0.429229	0.225517	−0.143122	0.064*
H8B	0.282320	0.234978	−0.166386	0.064*
C13	0.1399 (4)	0.1365 (3)	0.1016 (2)	0.0549 (9)
H13	0.053142	0.160816	0.095097	0.066*
C14	0.1259 (10)	0.0496 (4)	0.0742 (4)	0.160 (3)
H14A	0.211128	0.024270	0.070552	0.192*
H14B	0.087983	0.049820	0.020316	0.192*
C15	0.0424 (10)	−0.0048 (5)	0.1290 (4)	0.177 (3)
H15A	−0.047564	0.010579	0.120265	0.212*
H15B	0.052024	−0.063498	0.112890	0.212*
C16	0.0718 (9)	0.0018 (4)	0.2159 (4)	0.134 (2)
H16A	0.005966	−0.027511	0.246482	0.161*
H16B	0.154610	−0.024623	0.227489	0.161*
C17	0.0760 (7)	0.0899 (4)	0.2398 (3)	0.1064 (19)
H17A	0.103583	0.093434	0.295890	0.128*
H17B	−0.010508	0.113445	0.235798	0.128*
C18	0.1671 (7)	0.1426 (4)	0.1884 (3)	0.1012 (18)
H18A	0.160640	0.201317	0.204736	0.121*
H18B	0.255302	0.124204	0.198629	0.121*
C3	0.1700 (6)	0.4820 (3)	0.0846 (4)	0.0852 (16)
H3A	0.091993	0.506405	0.106965	0.102*
H3B	0.240168	0.491776	0.122827	0.102*
C4	0.1999 (7)	0.5249 (3)	0.0077 (4)	0.0973 (19)
H4A	0.124308	0.522668	−0.027436	0.117*
H4B	0.218802	0.583958	0.018530	0.117*
C5	0.3105 (6)	0.4869 (3)	−0.0345 (4)	0.0921 (18)
H5A	0.389130	0.499251	−0.004276	0.111*
H5B	0.318083	0.512940	−0.087288	0.111*
C19	0.5337 (3)	0.2290 (2)	0.0854 (2)	0.0378 (7)
C20	0.6258 (3)	0.2314 (2)	0.15666 (19)	0.0354 (6)
C21	0.5963 (3)	0.1905 (2)	0.2283 (2)	0.0405 (7)
H21	0.520875	0.158523	0.231513	0.049*
C22	0.6777 (3)	0.1965 (2)	0.2952 (2)	0.0426 (8)
H22	0.657773	0.168502	0.342951	0.051*
C23	0.7891 (3)	0.2450 (2)	0.28989 (19)	0.0349 (6)
C24	0.8206 (3)	0.2858 (2)	0.2187 (2)	0.0437 (8)
H24	0.895536	0.318204	0.215589	0.052*
C25	0.7393 (3)	0.2778 (2)	0.1520 (2)	0.0430 (8)
H25	0.761216	0.303799	0.103596	0.052*
N2	0.8698 (2)	0.25446 (18)	0.36022 (16)	0.0359 (6)
C27	0.8318 (3)	0.2574 (3)	0.4385 (2)	0.0470 (8)
H27	0.746327	0.253900	0.455224	0.056*
N3	0.9303 (3)	0.2658 (3)	0.48687 (19)	0.0550 (8)
C26	1.0007 (3)	0.2624 (2)	0.3645 (2)	0.0423 (7)
H26	1.055193	0.263108	0.320125	0.051*

1 Source of material

All chemicals were purchased from commercial sources and used as received without further purification. An amount of 1 mmol tricyclohexyltin hydroxide and 1 mmol 4-(4H-1,2,4-triazol-4-yl)benzoic acid were added in CH₃OH (25 mL) and refluxed with agitating for 12 h. The reaction solution was filtered. Finally, the title crystal was precipitated by controlling solvent volatilization.

2 Experimental details

All H-atoms bonded to C atoms were placed geometrically and refined using a riding model with common isotropic displacement factors U_iso(H) = 1.2 or 1.5 U_eq(parent C-atom).

3 Comment

Organotin carboxylates, a class of organometallic compounds, have drawn considerable interest due to their diverse structures and significant biological activities [5, 6]. As these have shown higher apoptosis inducing character compared to the platinum complexes, both in vivo and in vitro, organotin carboxylates are found be the most promising alternatives [7, 8]. It is found that the activity and structure of organotin carboxylates are related. Therefore, the investigation on the crystal structures of organotin carboxylates has received wide attention [9, 10]. In this context, we have crystallized the title compound.

In the molecular structure (Figure), the Sn(IV) ion is four-coordinated by one oxygen atom of one carboxyl group and three carbon atoms of three cyclohexyl groups. Bond lengths and angles are all in the expected ranges [11–13]. The C–Sn–C angles and C–Sn–O angles are ranging from 112.29(15)^° to 124.37(14)^° and 90.93(12)^° to 101.76(11)^°, respectively. The bond lengths of Sn–C are ranging from 2.146(3) to 2.162(4) Å, and Sn1–O1 is 2.149(2) Å.

Corresponding author: Fuxing Zhang, Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hunan Provincial Key Laboratory of Functional Metal–Organic Compounds, School of Chemistry and Materials Science Hengyang Normal University Hengyang, Hunan 421008, China, E-mail: zhangfuxing@hynu.edu.cn

Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This work was supported by College Students Innovation and Entrepreneurship Training Program of Hunan Province General Project, College Students Innovation and Entrepreneurship Training Program of National General Project.
Competing interests: The authors declare no conflicts of interest regarding this article.

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Received: 2023-09-22

Accepted: 2023-10-25

Published Online: 2023-11-07

Published in Print: 2024-02-26

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