<i>Ab initio</i> structure determination of 3,4-diaminopyridin-1-ium dihydrogen phosphate

Bail, A. Le; Smrčok, Ľubomír

doi:10.1154/1.3660160

Cited by 6 publications

(11 citation statements)

References 33 publications

(32 reference statements)

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“…A comparison of the X-ray powder diffraction profiles calculated with the crystal structures from Le Bail and Smrčok and from the present study demonstrates that the profiles are virtually one and the same. They also coincide with the experimental diffraction profile obtained in this study.…”

Section: Resultssupporting

confidence: 60%

“…However, the structure of the dihydrogen phosphate salt (C 5 H 8 N 3 ·H 2 PO 4 , from here on, 3,4-DAPH + ·H 2 PO 4 – ; cf. Figure ), which is used therapeutically and is even patented together with the tartrate salt, had not been determined up until 2011, when its structure was solved and found to be monoclinic (space group I 2/ c ) by Le Bail and Smrčok from high-resolution powder diffraction . As part of a larger study for the development of 3,4-DAPH + ·H 2 PO 4 – , solid-state studies of this active pharmaceutical ingredient (API) have been carried out.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structure and Solid-State Properties of 3,4-Diaminopyridine Dihydrogen Phosphate and Their Comparison with Other Diaminopyridine Salts

Mahé¹,

Nicolaı̈²,

Allouchi

et al. 2013

Crystal Growth & Design

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3,4-Diaminopyridine is an active pharmaceutical ingredient for the treatment of Lambert–Eaton myasthenic syndrome (LEMS). It is 3,4-diaminopyridine dihydrogen phosphate that has become the active ingredient of choice. As part of a larger study for the development of this drug, solid-state studies have been carried out. At room temperature, the crystals are monoclinic (C2/c). Dihydrogen phosphate anions H2PO4 – form infinite chains parallel to the b axis, and these chains can be considered as macroanions (H2PO4)∞. The organic cations form hydrogen bonds with the macroanions bridging them together. A negative thermal expansion is observed along the [103] direction in the crystal, which coincides with the direction of chains of interchanging anions and cations. The crystal packing shows similarities with the hydrogen tartrate salt as illustrated by a Hirshfeld surface analysis. This phosphate and this tartrate salt are also the two diaminopyridine salts that have been selected for therapeutic use because of their appropriate physical properties.

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Section: Resultssupporting

confidence: 60%

Section: Introductionmentioning

confidence: 99%

Crystal Structure and Solid-State Properties of 3,4-Diaminopyridine Dihydrogen Phosphate and Their Comparison with Other Diaminopyridine Salts

Mahé¹,

Nicolaı̈²,

Allouchi

et al. 2013

Crystal Growth & Design

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“…Geometrical analysis of the optimized structures done by means of the PLATON program [43] showed that the originally proposed space group was correct. It has been previously proved that the DFT-optimized structure provides intermolecular distances certainly more accurate than those resulting from the Rietveld refinement which restrained the intramolecular interatomic distances to a quasi-rigid model [see, e.g., 44,45] …”

Section: Solid State Dft Structure Optimizationmentioning

confidence: 99%

Ab initio structure determination of kidney stone potassium quadriurate from synchrotron powder diffraction data, a 150 year problem solved

Bazin

Daudon

Elkaı̈m

et al. 2015

Comptes Rendus. Chimie

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a b s t r a c tThe structure of potassium urate, co-crystallized with uric acid K(C 5 H 3 N 4 O 3 )(C 5 H 4 N 4 O 3 ), from human kidney stones, is determined ab initio from synchrotron powder diffraction data, space group P2 1 /c, a ¼ 3.60504(9) Å, b ¼ 19.9293(7) Å, c ¼ 18.4841(6) Å, b ¼ 100.503(2) , Z ¼ 4. Each uric acid molecule is connected to a urate anion through three hydrogen bonds, both molecules are related by a pseudo-inversion center and are randomly distributed in the crystal. Two of the oxygen atoms of the uric acid molecule and two of the urate anions are involved in the potassium coordination forming KO 7 monocapped trigonal prisms sharing their triangular bases, building infinite chains extending along the short a axis. Such a formulation, though controversial, has been claimed to exist since 1862 and named potassium quadriurate. The crystal structure is optimized by energy minimization (DFT) in the solid state, using a hybrid PBE0 functional. The capacity of the urate anion to connect by strong hydrogen bonds to a uric acid molecule has implications concerning the uric acid transport in biological media.

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“…It was recently shown (see e.g. Smrčok et al 2007Smrčok et al , 2008Smrčok et al , 2009Smrčok et al , 2010Le Bail & Smrčok, 2011;Oszajca et al, 2012) that a combination of structure solution from powder data followed by structure refinement by energy minimization in the solid state can provide results whose Data reduction to |F hkl | for the decafluorocyclohex-1-ene test case by the Le Bail method using FullProf software. The neutron powder pattern was rebuilt [ = 1.909 Å , a = 11.915 (3), b = 7.247 (2), c = 9.663 (2) Å , = 113.34 (1) ] from the intensities given in the original paper (Pawley, 1981).…”

Section: Structure Solution and Optimizationmentioning

confidence: 99%

Decafluorocyclohex-1-ene at 4.2 K – crystal structure and theoretical analysis of weak interactions

Smrčok

Mach

Bail

2013

Acta Crystallogr Sect B

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The crystal structure of 1,2,3,3,4,4,5,5,6,6-decafluorocyclohex-1-ene (decafluorocyclohex-1-ene, C6F10) was solved in direct space from neutron powder diffraction data previously collected at 4.2 K [Pawley, G. S. (1981). J. Appl. Cryst. 14, 357-361] and refined by energy minimization in the solid state. To optimize the positions of the 64 atoms in the monoclinic computational cell the PBESOL and hybrid PBE0 functionals were used. The crystal structure of the title compound, which is liquid at room temperature, is built of antiparallel pairs of molecules assembled into molecular columns stacked along the a axis. Dominating the crystal-building forces are weak intermolecular dispersion interactions. Bonding conditions in the structure were analysed by theoretical molecular calculations of representative next-neighbor molecular dimers carried out using dispersion-corrected density functional theory (DFT) functionals and the SCS-MP2 wavefunction method. The largest interaction energy is of the order of ∼ 21 kJ mol(-1), above the interaction energy of a benzene dimer (11.3 kJ mol(-1)) and close to that of a water dimer (20.9 kJ mol(-1)). The interaction energy for the second most stable dimer can be compared with either that of a benzene dimer or of a C-H...π hydrogen bond. The remaining five weakly interacting dimers (∼ 4.2-8.4 kJ mol(-1)) can be characterized as having stronger interactions than those of methane dimers (-2.2 kJ mol(-1)), but weaker than those of benzene molecule pairs or weak C-H...C interactions for instance.

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Ab initio structure determination of 3,4-diaminopyridin-1-ium dihydrogen phosphate

Cited by 6 publications

References 33 publications

Crystal Structure and Solid-State Properties of 3,4-Diaminopyridine Dihydrogen Phosphate and Their Comparison with Other Diaminopyridine Salts

Crystal Structure and Solid-State Properties of 3,4-Diaminopyridine Dihydrogen Phosphate and Their Comparison with Other Diaminopyridine Salts

Ab initio structure determination of kidney stone potassium quadriurate from synchrotron powder diffraction data, a 150 year problem solved

Decafluorocyclohex-1-ene at 4.2 K – crystal structure and theoretical analysis of weak interactions

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