Startseite Naturwissenschaften Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S
Artikel Open Access

Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S

  • Zheng-Jun Liu ORCID logo EMAIL logo , Xiao-Miao Chen ORCID logo , Wei Zheng , Wu-Chao Zhou , Chang-Fu Wu und Fei-Fei Yang
Veröffentlicht/Copyright: 23. Oktober 2025

Abstract

C11H14N2O5S, tetragonal, P43 (no. 78), a = 8.1709(4) Å, c = 20.3262(11) Å, V = 1357.05(15) Å3, Z = 4, Rgt(F) = 0.0366, wRref(F2) = 0.0985, T = 273.15 K.

CCDC no.: 2031027

The molecular structure is shown in the figure. Table 1 contains the crystallographic data and the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.60 × 0.60 × 0.50 mm
Wavelength: CuKα radiation (1.54178 Å)
μ: 2.31 mm−1
Diffractometer, scan mode: Bruker Apex2, φ and ω scans
θmax, completeness: 72.3°, 99 %
N(hkl)measured, N(hkl)unique, Rint: 11095, 2616, 0.052
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2595
N(param)refined: 177
Programs: Bruker, 1 Olex2, 2 Shelx 3 , 4

1 Source of material

In a round-bottomed flask, α-alanine (4.45 g, 50.00 mmol), sodium hydroxide (4.00 g, 100.00 mmol) and 100 mL of deionized water were added. After stirring to effect dissolution, 4-acetamidobenzenesulfonyl chloride (11.68 g, 50.00 mmol) was added, and the mixture was stirred at room temperature for 10 h. Then, the pH of the mixture was adjusted to 1 with 6 mol/L hydrochloric acid, and a white solid precipitated. After filtration, washing with deionized water and drying at room temperature, the white solid (286.3 mg, 1.00 mmol) was dissolved in a 1:1 methanol-water solution and allowed to volatilize naturally. Colorless block crystals of the title compound were precipitated after one week.

2 Experimental details

Hydrogen atoms were added using riding models. Their Uiso values were set to 1.2Ueq of the parent atoms. The structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL. 4

3 Comment

Sulfonylated amino acids have emerged as versatile building blocks in the construction of organometallic complexes, primarily owing to their diverse coordination modes arising from the presence of multiple potential donor sites. 5 , 6 , 7 To date, numerous comprehensive reports have documented organometallic complexes of 4-acetamidobenzenesulfonylglycine. 8 , 9 , 10 In an effort to further elucidate how subtle structural modifications influence coordination properties, the present work investigates the impact of introducing a methyl substituent onto the glycine moiety of 4-acetamidobenzenesulfonylglycine. Toward this end, we have successfully synthesized a new sulfonylated amino acid through the reaction of 4-acetamidobenzenesulfonyl chloride with α-alanine.

The title compound crystallizes in the tetragonal system with the space group P43. In the asymmetric unit, there is one complete ((4-acetamidophenyl)sulfonyl)-l-alanine molecule. The molecular framework retains structural features derived from both starting materials. The aromatic moiety, originating from 4-acetamidobenzenesulfonyl chloride, forms the core benzene ring, characterized by typical C–C bond lengths (1.373(4)–1.397(4) Å) and bond angles (119.5(3)–120.6(3)) consistent with aromatic character. These bond lengths and bond angles are comparable to the corresponding ones of the reported ((4-acetamidophenyl)sulfonyl)glycine molecule. 9 Attached to the benzene ring is a sulfonyl group (–SO2–), a remnant of the sulfonyl chloride precursor, where the central S1 atom exhibits tetrahedral coordination with two double bonds to O2 (1.427(3) Å) and O3 (1.433(2) Å), a single bond to N2 (1.610(3) Å), and a single bond to C6 (1.764(3) Å). In the reported ((4-acetamidophenyl)sulfonyl)glycine molecule, the corresponding bond lengths are 1.4344(16) Å, 1.4350(16) Å, 1.6222(17) Å and 1.761(2) Å, respectively. 9 On the other side of the benzene ring, C3 is attached to an acetamido group. The α-alanine-derived segment is evident in the amino acid chain: The C11 atom bears a carboxyl group (O4–C11 = 1.203(4) Å, O5–C11 = 1.308(4) Å), a key functional group from α-alanine. In the reported ((4-acetamidophenyl)sulfonyl)glycine molecule, the corresponding bond lengths are 1.195(3) Å and 1.310(3) Å, respectively. 9 Intermolecular stabilization is provided by at least a hydrogen bond between O5–H5 and the oxygen atom O1 of an adjacent molecule [d(O5⋯O1) = 2.582(4) Å, ∠O5–H5⋯O1 = 162.2°].


Corresponding author: Zheng-Jun Liu, Key Laboratory of Agricultural Resources and Environment in High Education Institute of Guizhou Province, Anshun University, Anshun, 561000, P.R. China, E-mail:

Acknowledgments

This work was financially supported by General Program of Guizhou Provincial Basic Research Program (Natural Science) (Qianjiaohe Jichu MS[2025]072), Anshun “Two Cities and Three Bases” Youth Science and Technology Talents Training Program (Anshi Ke Ren [2024]4), the Doctoral Fund of Anshun University (asxybsjj202314).

References

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Received: 2025-08-09
Accepted: 2025-10-06
Published Online: 2025-10-23
Published in Print: 2025-12-17

© 2025 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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