Study and characterization of crystalline hydrate/polymorph forms of 5,11-dihydro-11-ethyl-5-methyl-8-(2-(1-oxido-4-quinolinyl)ethyl-6H-dipyrido(3,2-B:2′,3′-E)(1,4)diazepin-6-one by solid-state NMR and solution NMR

Gonnella, Nina C.; Smoliga, John A.; Campbell, Scot; Busacca, Carl A.; Cerreta, Michael; Varsolona, Richard J.; Norwood, Daniel L.

doi:10.1016/j.jpba.2009.11.012

Cited by 5 publications

(28 citation statements)

References 21 publications

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“…The 19 F→ 13 C CPMAS experiments, carried out with 1 H decoupling, yields identical NMR spectra for both forms of Xaliproden as shown in Figure 7a (i) and (ii). The spectra contain resonances in the range 120-140 ppm, characteristic of aromatic carbon atoms close to the F atoms, confirmed by the assignment of the Xaliproden NMR spectra in liquid form ( Table 4).…”

Section: Solid-state Nmrmentioning

confidence: 78%

“…Contact times of 3 to 5 ms were used and recycle delay was set to 8 sec for each sample. 19 F and 13 C, respectively) using a 4 mm triple channels probe. 1 H and 19 F RF field of 80 and 70 kHz were used for SPINAL-64 decoupling during acquisition of the 13 C signal, respectively.…”

Section: Solid-state Nmrmentioning

confidence: 99%

“…1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 14 has been applied to further the description of the polymorphism in Xaliproden Forms I and III and the results are presented and discussed in the following sections. 19 F-13 C CPMAS.…”

Section: Solid-state Nmrmentioning

confidence: 99%

“…We shall present a detailed structural investigation of the polymorphism of Xaliproden hydrochloride, using single crystal XRD, synchrotron powder XRD and solid-state high-resolution 13 C CPMAS NMR. In particular, we used various CP transfer conditions (from 1 H to 13 C and from 19 F to 13 C) as well as various decoupling schemes ( 1 H single decoupling and 1 H-19 F double decoupling) to characterize the phases, from both a structural and a dynamical point of view. In the light of the results, the minute structural differences found between two of the three polymorphs are accounted for by assuming a discrete jumps of the CF 3 group.…”

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confidence: 99%

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Polymorphism in Xaliproden (SR57746A): An X-ray Diffraction, Calorimetric, and Solid-State NMR Investigation

Chandrappa

Ochsenbein

Martineau

et al. 2013

Crystal Growth & Design

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Three polymorphic phases of Xaliproden are evidenced through thermal analysis: Form II has an orthorhombic symmetry while Forms I and III have monoclinic unit cells. Structural characterizations of Xaliproden are carried out by means of single-crystal and synchrotron powder X-ray diffraction (XRD), as well as high-resolution solid-state 13 C cross-polarization at magic angle spinning (CPMAS) nuclear magnetic resonance (NMR) spectroscopy. Diffraction crystallography indicates that the structures of two of the polymorphs are highly similar despite different thermal events observed by thermal analysis. Further X-13 C (X = 1 H or 19 F) CPMAS NMR spectra, recorded under either 1 H or double-resonance 1 H/ 19 F decoupling, provide evidence for the occurrence of 19 F self-decoupling in Form III, indicating that the structural disorder observed in the X-ray diagram is dynamic, with rotation of the CF 3 group around the C-C single bond. The results show that polymorphism between Xaliproden Forms I and III mostly deals with the degree of freedom of the CF 3 group, higher in Forms III than in Form I and clarifies the status of Form III that can therefore be assigned to a well-defined polymorph of Xaliproden.

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Section: Solid-state Nmrmentioning

confidence: 78%

Section: Solid-state Nmrmentioning

confidence: 99%

Section: Solid-state Nmrmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Polymorphism in Xaliproden (SR57746A): An X-ray Diffraction, Calorimetric, and Solid-State NMR Investigation

Chandrappa

Ochsenbein

Martineau

et al. 2013

Crystal Growth & Design

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show abstract

“…128 The dihydrate and two anhydrate forms of 5,11-dihydro-11-ethyl-5-methyl-8-(2-(1-oxido-4-quinolinyl)ethyl-6H-dipyrido(3,2-B:2 , 3 -E)(1,4)diazepin-6-one have been studied by solidstate 13 C NMR to obtain information on molecular mobility and the degree of crystallinity. 129 In addition, mixtures of multiple forms could be detected on the basis of chemical shift patterns and relaxation measurements.…”

Section: Solvatomorphic Systemsmentioning

confidence: 99%