Startseite The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5
Artikel Open Access

The crystal structure of 1-phenylethan-1-aminium 4-hydroxy-3,5-dimethoxybenzoate C17H21NO5

  • Chen-Yu Ruan , Zi-Wei Ai , Gong-Yi Liang , Pan-Yue Cao , Ke-Fan Yu und Cheng-Jun Jiang ORCID logo EMAIL logo
Veröffentlicht/Copyright: 8. Januar 2025

Abstract

C17H21NO5, monoclinic, P21 (no. 4), a = 6.0322(2) Å, b = 16.0271(6) Å, c = 9.0421(3) Å, β = 105.568(2)°, V = 842.11(5) Å3, Z = 2, Rgt(F) = 0.0384, wRref(F2) = 0.1008, T = 170 K.

CCDC no.: 2404816

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: Colourless needle
Size: 0.18 × 0.05 × 0.03 mm
Wavelength: Ga Kα radiation (1.34139 Å)
μ: 0.49 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE Metaljet PHOTON III, φ and ω
θmax, completeness: 60.7°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 34479, 3792, 0.051
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ (Iobs), 3,632
N(param)refined: 213
Programs: Bruker, 1 Olex2, 2 SHELX 3 , 4
Table 2:

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

Atom x y z Uiso*/Ueq
O1 0.2862 (3) 0.47435 (11) 0.7036 (2) 0.0337 (4)
O2 0.5642 (3) 0.53971 (9) 0.62928 (19) 0.0274 (4)
O3 0.9111 (3) 0.30349 (9) 0.37742 (18) 0.0254 (3)
O4 0.7197 (3) 0.16744 (9) 0.44234 (19) 0.0255 (3)
H4 0.617578 0.131280 0.438785 0.038*
O5 0.4078 (3) 0.16696 (10) 0.6039 (2) 0.0359 (4)
C9 0.4571 (3) 0.47486 (14) 0.6496 (2) 0.0207 (4)
C10 0.5338 (3) 0.39225 (12) 0.6003 (2) 0.0189 (4)
C11 0.6979 (3) 0.39013 (12) 0.5169 (2) 0.0193 (4)
H11 0.768346 0.440257 0.496376 0.023*
C12 0.7574 (3) 0.31415 (13) 0.4640 (2) 0.0200 (4)
C13 0.6565 (3) 0.24031 (13) 0.4962 (2) 0.0203 (4)
C14 0.4938 (3) 0.24352 (13) 0.5811 (2) 0.0218 (4)
C15 0.4309 (3) 0.31905 (14) 0.6322 (2) 0.0206 (4)
H15 0.318728 0.320952 0.688400 0.025*
C16 0.9935 (4) 0.37776 (15) 0.3221 (3) 0.0300 (5)
H16A 0.864074 0.407652 0.253949 0.045*
H16B 1.105195 0.362882 0.265247 0.045*
H16C 1.067728 0.413591 0.409091 0.045*
C17 0.2517 (4) 0.16324 (15) 0.6970 (3) 0.0307 (5)
H17A 0.118255 0.198762 0.652385 0.046*
H17B 0.328757 0.182870 0.800665 0.046*
H17C 0.200559 0.105521 0.701948 0.046*
N1 0.0152 (3) 0.60159 (11) 0.7428 (2) 0.0243 (4)
H1A 0.033719 0.646696 0.686167 0.029*
H1B −0.134296 0.584728 0.713411 0.029*
H1C 0.107470 0.559356 0.727597 0.029*
C1 0.0617 (4) 0.75928 (16) 1.0460 (3) 0.0305 (5)
H1 0.221535 0.753240 1.093806 0.037*
C2 −0.0570 (4) 0.82650 (16) 1.0832 (3) 0.0309 (5)
H2 0.020978 0.865790 1.157807 0.037*
C3 −0.2888 (4) 0.83660 (13) 1.0119 (3) 0.0276 (5)
H3 −0.369249 0.883328 1.036260 0.033*
C4 −0.4036 (4) 0.77855 (14) 0.9050 (2) 0.0259 (4)
H4A −0.562741 0.785513 0.855959 0.031*
C5 −0.2860 (4) 0.71027 (14) 0.8698 (2) 0.0255 (4)
H5 −0.365868 0.669996 0.797955 0.031*
C6 −0.0520 (4) 0.70032 (14) 0.9387 (2) 0.0248 (4)
C7 0.0787 (5) 0.62458 (17) 0.9092 (3) 0.0351 (5)
H7 0.246282 0.638777 0.940100 0.042*
C8 0.0440 (8) 0.5509 (2) 1.0033 (4) 0.0679 (12)
H8A −0.119706 0.536195 0.976578 0.102*
H8B 0.096096 0.565014 1.112591 0.102*
H8C 0.132872 0.503320 0.982033 0.102*

1 Source of materials

The mixture of syringic acid (121 mg, 0.6 mmol) and of α-methylbenzylamine (80 ml, 0.6 mmol) were dissolved in a mixture of 3.5 ml acetonitrile and 1.5 ml ethanol, and the resulting mixture was stirred at 60 °C for 2 h to obtain a clarified solution. Cool to 40 °C, and then put it in a 10 ml glass bottle. The glass bottle was covered with a porous film. Single crystals of the title compound were obtained after 1 day.

2 Experimental details

Absorption corrections were applied by using multi-scan program. 1 Using Olex2, 2 the structure was solved with the ShelXT 3 structure solution program and refined with the ShelXL 4 refinement package. The H atoms were fixed, fixed Uiso were set to 1.2 times of all C(H) groups, C(H, H) groups and N(H, H) groups; 1.5 times of C(H, H, H), groups, O(H) groups and O(H, H) groups.

3 Comment

Syringic acid (SA) has interesting applications on pharmaceutical, fragrance and favour industries. It is the low molecular weight compound obtained through an oxidation process of the lignin. 5 Separation and purification processes to obtain purified SA from oxidation products of lignin are important. 6 Accordingly, the development of sustainable purification and recovery processes of high-value compounds from industry waste, suitable for industrial implementation, is nowadays a crucial need. In this work, a salt of SA with a phenylethylamine (PEA) is designed, synthesized, and characterized. It can provide a method for purifying SA. The title structure was refined to contain one host SA anion and one guest PEA cation: the nitrogen atom of the guest is protonated, while the C–O bond lengths of the host carboxylic group have lengthened from the usual values of 1.20 Å as occurs in the C=O double bond to 1.254(3) Å in the delocalized COO– anion. This is in accordance with the publication of Park 7 which discusses the salt-cocrystal continuum as a function of pKa of acid–base structures: the pKa of SA is 4.34 while that of protonated PEA is 9.73 resulting in a pKa of 5.39. This is a sufffciently large difference to predict the formation of a salt. Bond lengths are as expected. 8 , 9


Corresponding author: Cheng-Jun Jiang, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou, Liuhe Road 318#, China, E-mail:

Acknowledgements

We would also like to thank Mr Jiyong Liu from the Chemistry Instrumentation Center Zhejiang University for X-ray crystallographic analysis.

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

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

References

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Received: 2024-12-01
Accepted: 2024-12-28
Published Online: 2025-01-08
Published in Print: 2025-04-28

© 2024 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
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  6. Crystal structure of tetramethyl-bis(μ2-2-(2-hydroxy-3-methoxybenzylidene)-1-(6-(2-(2-hydroxy-3-methoxybenzylidene)hydrazine-1-carbonyl)picolinoyl)hydrazin-1-ido-κ4O,N,O′:O′)ditin(II) ─ ethanol (1/2), C54H62N10O14Sn2
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  8. The crystal structure of cyclopentadienyl Co–P–C complexes by benzylideneacetone addition, C38H38CoO2P
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  27. The crystal structure of barium hexahydroxidoiridate(IV) dihydroxide, Ba2[Ir(OH)6](OH)2
  28. Crystal structure of cinnamoyl ferrocene, C19H16FeO
  29. Crystal structure of (E)-3-(4-butoxyphenyl)acryloylferrocene, C23H24FeO2
  30. Crystal structure of 7-(dimethylamino)-2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-ethyl carboxylate, C15H16F3NO4
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