The crystal structure of 2-benzylsuccinic acid, C11H12O6 Z. Kristallogr. - New Cryst. Struct.
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Caiyu Zhang
,
Fengfeng Wang
,
Hua Chen
Abstract
C11H12O4, orthorhombic, Pna21 (no. 33), a = 18.9628(4) Å, b = 5.58910(10) Å, c = 9.6527(2) Å, V = 1023.04(4) Å3, Z = 4, Rgt(F) = 0.0308, wR ref (F2) = 0.0849, T = 297 K.
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.
Data collection and handling.
| Crystal: | Colourless plate |
| Size: | 0.05 × 0.04 × 0.01 mm |
| Wavelength: μ: |
Cu Kα radiation (1.54184 Å) 0.87 mm−1 |
| Diffractometer, scan mode: θmax, completeness: |
XtaLAB Synergy R, ω scans 76.2°, 100 % |
| N(hkl)measured, N(hkl)unique, Rint: | 12070, 2078, 0.059 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2009 |
| N(param)refined: | 144 |
| Programs: | Rigaku, 1 Olex2, 2 SHELX 3 , 4 |
1 Source of materials
The (R)-2-benzylsuccinic acid and (S)-2-benzylsuccinic acid were bought from Shanghai Titan Technology Co. Ltd. About 25 mg (R)-2-benzylsuccinic acid and (S)-2-benzylsuccinic acid powder were placed into a 10 ml penicillin bottle, followed by addition of 2 ml deionized water. After the suspension solution was thoroughly mixed, the penicillin bottle was sealed with a cap and placed in an oven. The bottle was maintained at a temperature of 350 K until all the powder was completely dissolved. The vial was then removed from the oven and left at room temperature. After one week, plate crystals were harvested.
2 Experimental details
The positions of hydrogen atoms on carbon atoms were calculated geometrically and refined using the riding model. The hydrogen atom on oxygen atoms were located from difference Fourier map and refined with Uiso (H) = 1.5 Ueq(O). The distances between the hydrogen atom and the oxygen atom were refined freely. A DFIX restrain was used to get a better model for the hydrogen atoms. Flack parameter was determined using 903 quotients using Parsons’ method, 5 giving value of 0.5(3).
3 Comment
The titled compound is the racemate of (S)-benzylsuccinic acid 6 and (R)-benzylsuccinic acid. 7 The titled compound is employed as a carboxypeptidase A inhibitor. 8 The binding between this title compound and carboxypeptidase A can be confirmed by X-ray diffraction. 9 , 10 , 11
The titled compound was crystallized in Pna21 space group with one molecule in its asymmetric unit. The bond lengths and angles within these moieties are in the expected ranges. There is one benzene ring and two carboxyl groups in the molecule. The carbon-oxygen bond lengths on the carboxyl groups are 1.298(2) Å and 1.224(2) Å, 1.294(2) Å and 1.226(2) Å respectively. The difference in bond length between the carbon-oxygen single bond and the carbon-oxygen double bond is slightly larger than the value reported in the literature. 6 The hydrogen bond lengths are 2.636(2) Å (O1⋯O41/2−X, −1/2+Y, 1/2+Z) and 2.694(2) Å (O3⋯O21/2−X, 1/2+Y, −1/2+Z) respectively. A one-dimensional chain is formed along the [0–11] direction through the hydrogen bonds mentioned above. Geometric parameters are all in the expected ranges. 11
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Conflict of interest: The authors declare no conflicts of interest regarding this article.
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Research funding: Discipline construction of Institute of Chemical Drugs, NIFDC (No. 2025HYZX08).
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Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
References
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