Home The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2
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The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2

  • Jing Zhou ORCID logo EMAIL logo
Published/Copyright: February 6, 2024

Abstract

C18H16B2N2, monoclinic, C2/c (no. 15), a = 34.048(12) Å, b = 5.720(2) Å, c = 7.666(3) Å, β = 96.803°, V = 1482.5(9) Å3, Z = 4, R gt (F) = 0.0412, wR ref (F2) = 0.1152, T = 150 K.

CCDC no.: 2299849

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 block
Size: 0.20 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.07 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 26.7°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 7378, 1574, 0.029
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1093
N(param)refined: 100
Programs: Bruker [2], SHELX [35], Olex2 [1]
Table 2:

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

Atom x y z Uiso*/Ueq
N1 0.40650 (3) 0.4701 (2) 0.50002 (15) 0.0259 (3)
H1 0.406508 0.603313 0.557510 0.031*
C2 0.37019 (4) 0.3649 (2) 0.45040 (17) 0.0246 (3)
C3 0.36942 (4) 0.1472 (2) 0.36151 (17) 0.0261 (3)
C4 0.40597 (4) 0.0396 (2) 0.32636 (18) 0.0293 (3)
H4 0.405008 −0.107744 0.268749 0.035*
C5 0.33468 (4) 0.4694 (3) 0.48504 (18) 0.0286 (3)
H5 0.335260 0.614212 0.545966 0.034*
C6 0.44159 (4) 0.1411 (3) 0.37260 (19) 0.0299 (4)
H6 0.465107 0.065007 0.347821 0.036*
C7 0.48169 (4) 0.5275 (3) 0.51745 (18) 0.0296 (3)
H7 0.478661 0.668996 0.579352 0.035*
C8 0.33238 (4) 0.0435 (3) 0.30865 (18) 0.0328 (4)
H8 0.331292 −0.102090 0.248570 0.039*
C9 0.29892 (4) 0.3633 (3) 0.4312 (2) 0.0344 (4)
H9 0.274984 0.435886 0.454514 0.041*
C1 0.29775 (5) 0.1490 (3) 0.3424 (2) 0.0370 (4)
H1 0.273062 0.076521 0.305533 0.044*
B1 0.44387 (5) 0.3794 (3) 0.4652 (2) 0.0269 (4)

1 Source of materials

The title compound was synthesized from a mixture of catalytic Grubbs 2nd generation catalyst and 2-vinyl-1,2-dihydrobenzo[e][1,2]azaborinine [1] suspended in dichloroethane under N2 atmosphere at room temperature for 1 week. Until the completion of this reaction, the resulting residue was adsorbed onto silica gel by rotary evaporation of a DCM solution, loaded directly onto a silica gel column by eluting with EtOAc:PE 1:10 to get the target product as white solid. The crystal structure of this target product was formed and obtained in a mixed system of n-hexane and dichloromethane.

2 Experimental details

Semi-empirical absorption corrections were applied using SADABS program [2]. The structures were solved with SHELXT-2018, and the non-hydrogen atoms were refined anisotropically using the SHELXL-2019 crystallographic software [1, 4]. All the hydrogen atoms were introduced at the calculated positions.

3 Comment

Stilbene derivatives are a series of molecules with a double bond connecting two benzene rings as a skeleton structure. Stilbenes are widely found in natural products, and have many biological activities such as anti-oxidation, antibacterial, anti-inflammatory, anti-platelet agglutination, and preventing cell cancerization [6]. When the two benzene rings on stilbene are changed to two naphthalene rings, the skeleton is 1,2-di(naphthalen-2-yl)ethene (DNE). Naphthalene is an extensively explored aromatic conjugated system with applications in various pathophysiological conditions [7]. Vinylnaphthalene can be widely used as pharmaceutical intermediates, dye intermediates, and optical component coating materials. BN 2-vinylnaphthalene, as a polar olefin monomer, has attracted the research interest of polymer scholars due to its unique structural characteristics [8], [9], [10]. However, the chemistry and biological activity of DNE are rarely studied. Especially, BN substituted 1,2-di(naphthalen-2-yl)ethene (BN–DNE) has never been constructed. Here we reported the synthesis and unique structure of BN substituted 1,2-di(naphthalen-2-yl)ethene. Furthermore, we compared the crystal structure of DNE (CCDC number, 1555496) and BN–DNE.

Single-crystal X-ray diffraction (SC–XRD) measurement result showed that each asymmetric unit contains one half (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene molecule. As shown in the Figure, the central boron atom B1 adopts a typical three-coordinated planar triangular geometry surrounded by two carbon atoms (C6, C7) and one nitrogen atom (N1). The C/N–B bond lengths and C/N–B–C/N bond angles are in the range of 1.4284(19)–1.554(2) and 114.32(13)–126.76(13)°, respectively, which are comparable to some previously reported boron-containing compounds with the similar structure [5], [6], [7]. Due to the planar geometry of boron atoms and the linkage of C=C bond, all the atoms of this molecule are closely coplanar. In addition, in the crystal structure of 1, adjacent molecules are assembled by C–H⋯π interactions into two-dimensional (2D) supramolecular layers, which are further stacked to the final 3D structure.

The crystal of (E)-1,2-di(naphthalen-2-yl)ethene (DNE) crystallized in the space group P21/c and each asymmetric unit consists of one half DNE molecule. Meanwhile, all the atoms in compound 1 and DNE are both closely coplanar due to the planar geometry of C=C bond and the aromatic rings. In addition, significant C–H⋯π interactions could be observed between the adjacent DNE molecules as well with the similar dihedral angle to that of compound 1, but the interacted H atoms are located on the same six-membered ring, which is quite different from compound 1. On the other hand, the adjacent two molecules in the crystal of compound 1 are intertwined with each other and their projections on the ab plane are X shape, while the neighboring two molecules in DNE are side-by-side with the projections nearly parallel to each other. Further inspection revealed that the adjacent DNE molecules are also assembled by the C–H⋯π interactions into layers, which is similar to the crystal structure of 1.


Corresponding author: Jing Zhou, College of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, Shaanxi Province, P.R. China, E-mail:

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: No. 22201169

Funding source: Innovation Team of Xianyang City

Award Identifier / Grant number: S2023-CXNL-CXTD-2110

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

  2. Research funding: National Natural Science Foundation of China (No. 22201169), Innovation Team of Xianyang City (S2023-CXNL-CXTD-2110).

  3. Conflict of interest statement: The author declares no conflicts of interest regarding this article.

References

1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

2. SAINT. Program for Data Extraction and Reduction; Bruker AXS, Inc: Madison, WI, 2001.Search in Google Scholar

3. Sheldrick, G. M. SADABS, Program for Empirical Adsorption Correction of Area Detector Data; University of Göttingen: Germany, 2003.Search in Google Scholar

4. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

5. Sheldrick, G. M. SHELXL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8.10.1107/S2053273314026370Search in Google Scholar PubMed PubMed Central

6. Wang, S., Yang, H. J., Xu, X. L., Liu, M., Zhan, C., Wen, H. L. Synthesis of stilbene derivatives and determination of antifungal activity. J. Shenyang Pharmaceut. Univ. 2020, 37, 223–230.Search in Google Scholar

7. Makar, S., Saha, T., Singh, S. K. Naphthalene, a versatile platform in medicinal chemistry: sky-high perspective. Eur. J. Med. Chem. 2019, 161, 252–276; https://doi.org/10.1016/j.ejmech.2018.10.018.Search in Google Scholar PubMed

8. van de Wouw, H. L., Lee, J. Y., Klausen, R. S. Gram-scale free radical polymerization of an azaborine vinyl monomer. Chem. Commun. 2017, 53, 7262–7265; https://doi.org/10.1039/c7cc02300f.Search in Google Scholar PubMed

9. van de Wouw, H. L., Lee, J. Y., Awuyah, E. C., Klausen, R. S. A BN aromatic ring strategy for tunable hydroxy content in polystyrene. Angew. Chem. Int. Ed. 2018, 57, 1673–1677; https://doi.org/10.1002/anie.201711650.Search in Google Scholar PubMed

10. Huang, J., Jiang, Y., Zhang, Z., Li, S., Cui, D. Stereoselective polymerization of an aromatic vinyl monomer to access highly syndiotactic poly(vinyl alcohol). Macromol. Rapid Commun. 2020, 41, 2000038–2000043; https://doi.org/10.1002/marc.202000038.Search in Google Scholar PubMed

Received: 2023-11-09
Accepted: 2023-12-27
Published Online: 2024-02-06
Published in Print: 2024-04-25

© 2023 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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