A Single Crystal Study On 2-(methylcarbamoyl)benzoic Acid, C9H9NO3

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BY-NC-ND 3.0 license Open Access Published by De Gruyter (O) September 16, 2017 Purchase article A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3
  • Pengfei Wei EMAIL logo , Xiao-Li Yang and Kun-Yan Wang
From the journal Zeitschrift für Kristallographie - New Crystal Structures https://doi.org/10.1515/ncrs-2017-0078 Download article (PDF) Supplementary Materials Cite this Share this

Abstract

C9H9NO3, monoclinic, P21/c (no. 14), a = 8.7201(8) Å, b = 8.6453(9) Å, c = 11.8083(9) Å, β = 100.830(3)°, V = 874.35(14) Å3, Z = 4, Rgt(F) = 0.0489, wRref(F2) = 0.1142, T = 296(2) K.

CCDC no.:: 1569093

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Colourless block
Size:0.28 × 0.21 × 0.17 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.0 cm−1
Diffractometer, scan mode:PHOTON100 CMOS, ω scans
2θmax, completeness:50.8°, >99%
N(hkl)measured, N(hkl)unique, Rint:7023, 1603, 0.072
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1127
N(param)refined:125
Programs:CAD-4 [1, 2] , SHELX [3, 4]
Table 2

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

AtomxyzUiso*/Ueq
C10.7659(2)0.9801(2)0.65405(17)0.0178(5)
C20.7244(2)0.9605(2)0.76231(17)0.0188(5)
C30.8129(3)0.8626(3)0.84236(19)0.0292(6)
H30.78400.84760.91520.035*
C40.9419(3)0.7869(3)0.81791(19)0.0348(6)
H41.00250.72250.87450.042*
C50.9830(3)0.8044(3)0.71166(19)0.0299(6)
H51.07100.75110.69430.036*
C60.8954(2)0.9003(3)0.63019(19)0.0233(5)
H60.92380.91190.55690.028*
C70.6744(2)1.0860(2)0.56710(17)0.0194(5)
C80.5960(2)1.0504(2)0.80081(16)0.0175(5)
C90.3470(3)1.0341(3)0.8655(2)0.0357(6)
H9A0.37981.13260.90360.054*
H9B0.31710.96210.92170.054*
H9C0.25761.05160.80300.054*
N10.4755(2)0.9687(2)0.81858(15)0.0230(5)
H1B0.467(3)0.871(3)0.7987(19)0.028*
O10.74698(18)1.1135(2)0.47935(13)0.0296(4)
H1A0.692(3)1.175(3)0.428(2)0.036*
O20.55076(17)1.14259(18)0.57593(11)0.0247(4)
O30.61125(16)1.19134(17)0.82207(11)0.0238(4)

Source of materials

The title compound, can be synthesized according to the literature [5]. In a typical reaction 0.5 g of the title compound was dissolved in 8 mL methanol. Evaporation at room temperature yielded colorless crystals of 2-(methylcarbamoyl)benzoic acid.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses and either placed on calculated positions with the help of the SHELXL program (AFIX 43 or 137 option for alkyl and aromatic hydrogens) [3] or freely refined with Uiso(H) = 1.2Ueq(N,O).

Comment

The compound we report here is a very important impurity in the production of milnacipran hydrochloride. Milnacipran hydrochloride is a serotonin-norepinephrine reuptake inhibitor (SNRI) used in the clinical treatment of fibromyalgia that was first approved for the treatment of major depressive episodes in France in December 1996. The bond lengths and angles in the crystal structure are within normal ranges [6]. The carboxyl (C7/O1/O2) and acylamide (C8/O3/N1/C9) groups are oriented at 11.3(3)° and 70.6(4)° with respect to the benzene ring (C1/C2/C3/C4/C5/C6) to which they are bonded. In the crystal of the title compound there are O—H⋯O and N—H⋯O intermolecular bydrogen bonds, but no π-π stacking interactions, as the centroid to centroid distance between the two nearest rings is larger than 4 Å.

Acknowledgement

This work is supported by the PhD Research Startup Foundation of Jinling Institute of Technology (JIT-B-201211 and JIT-B-201323).

References

Enraf-Nonius: CAD-4 Software. Version 5.0. Enraf-Nonius, Delft, The Netherlands, (1985).Search in Google Scholar

Harms, K.; Wocadlo, S.: XCAD4. University of Marburg, Germany, (1995).Search in Google Scholar

Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

John, W. V.; Louella, W.: Thermolysis of N-alkyl-substituted phthalamic acids. Steric inhibition of imide formation. J. Org. Chem. 46 (1981) 175–177.10.1021/jo00314a039Search in Google Scholar

Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R.: Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J. Chem. Soc. Perkin Trans. 2 (1987) S1–S19.10.1039/p298700000s1Search in Google Scholar

Received: 2017-3-23Accepted: 2017-8-15Published Online: 2017-9-16Published in Print: 2017-11-27

©2017 Pengfei Wei et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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Wei, Pengfei, Yang, Xiao-Li and Wang, Kun-Yan. "A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3" Zeitschrift für Kristallographie - New Crystal Structures, vol. 232, no. 6, 2017, pp. 917-918. https://doi.org/10.1515/ncrs-2017-0078 Wei, P., Yang, X. & Wang, K. (2017). A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3. Zeitschrift für Kristallographie - New Crystal Structures, 232(6), 917-918. https://doi.org/10.1515/ncrs-2017-0078 Wei, P., Yang, X. and Wang, K. (2017) A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3. Zeitschrift für Kristallographie - New Crystal Structures, Vol. 232 (Issue 6), pp. 917-918. https://doi.org/10.1515/ncrs-2017-0078 Wei, Pengfei, Yang, Xiao-Li and Wang, Kun-Yan. "A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3" Zeitschrift für Kristallographie - New Crystal Structures 232, no. 6 (2017): 917-918. https://doi.org/10.1515/ncrs-2017-0078 Wei P, Yang X, Wang K. A single crystal study on 2-(methylcarbamoyl)benzoic acid, C9H9NO3. Zeitschrift für Kristallographie - New Crystal Structures. 2017;232(6): 917-918. https://doi.org/10.1515/ncrs-2017-0078 Copy to clipboard Download: BibTeX EndNote RIS Share this article
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