10,11-Dihydrocarbamazepine (form III)

Leech, Charlotte K.; Florence, Alastair J.; Shankland, Kenneth; Shankland, Norman; Johnston, Andrea

doi:10.1107/s1600536806053335

Cited by 15 publications

(18 citation statements)

References 7 publications

(6 reference statements)

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“…This is thought to allow for the optimization of the hydrogen bonding in a chain motif 13. All three structures of dihydrocarbamazepine also exhibit an analogous hydrogen bonding scheme to OCB, as they all form hydrogen bonded chains 7–9. The hydrogen bonding in all four of the carbamazepine polymorphs favor an anti‐dimer motif,6 whereas the structure of epoxycarbamazepine displays a twisted syn‐dimer configuration 18.…”

Section: Resultsmentioning

confidence: 99%

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Crystal polymorphism in a carbamazepine derivative: Oxcarbazepine

Lutker

Matzger

2010

Journal of Pharmaceutical Sciences

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Although crystal polymorphism of carbamazepine (CBZ), an anticonvulsant used to treat epilepsy, has been known for decades, the phenomenon has only recently been noted for its keto-derivative oxcarbazepine (OCB). Here it is demonstrated that OCB possesses at least three anhydrous polymorphs. Although all forms are morphologically similar, making differentiation between crystal modifications by optical microscopy difficult, powder X-ray diffraction, Raman spectroscopy, and thermomicroscopy show distinctive differences. These techniques provide an efficient method of distinguishing between the three polymorphs. The crystal structure of form II of OCB is reported for the first time and the structure of form I has been redetermined at low temperature. Remarkably, both the molecular conformation and crystal packing of form II are in excellent agreement with the blind prediction made in 2007.

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Section: Resultsmentioning

confidence: 99%

“…Carbamazepine (CBZ) (Fig. 1), an important anticonvulsant, exhibits four structurally characterized polymorphs,6 whereas its dihydro derivative (10,11‐dihydrocarbamazepine) is trimorphic 7–9. Its keto‐derivative, oxcarbazepine (OCB) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Crystal polymorphism in a carbamazepine derivative: Oxcarbazepine

Lutker

Matzger

2010

Journal of Pharmaceutical Sciences

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“…The single‐crystal structure of sulfapyridine Form‐VI has been described, demonstrating that the asymmetric unit contains two different tautomeric forms that formed separate hydrogen‐bonded networks which interpenetrate 67. The crystal structures of new polymorphic forms of carvedilol,68 palonosetron hydrochloride,69 and 10,11‐dihydrocarbamazepine70 have been reported, and it has been shown that the crystal structure of methyl paraben obtained at a temperature of 118 K does not represent a new polymorph 71…”

Section: Structural Characterization and Properties Of Polymorphs Andmentioning

confidence: 99%

Polymorphism and Solvatomorphism 2007

Brittain¹

2009

Journal of Pharmaceutical Sciences

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“…For details of experimental methods used to obtain this compound, see: Florence et al (2003); Florence, Johnston, Fernandes et al (2006). For related crystal structures, see: Bandoli et al (1992); Cyr et al (1987); Harrison et al (2006); Leech et al (2007); Fleischman et al (2003); Florence, Johnston, Price et al (2006); Florence, Leech et al (2006); Johnston et al (2006Johnston et al ( , 2007. For related literature, see: Etter (1990).…”

Section: Related Literaturementioning

confidence: 99%

10,11-Dihydrocarbamazepine–formamide solvate (1/1)

et al. 2007

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Key indicators: single-crystal X-ray study; T = 120 K; mean (C-C) = 0.003 Å; R factor = 0.074; wR factor = 0.193; data-to-parameter ratio = 63.7.In the title compound {systematic name: 10,11-dihydro-5Hdibenz[b,f]azepine-5-carboxamide-formamide solvate (1/1)}, C 15 H 14 N 2 OÁCH 3 NO, the dihydrocarbamazepine and formamide molecules are hydrogen bonded to form an R 2 2 (8) dimer, which is further connected to form a ladder motif. Experimental Crystal data C 15 H 14 N 2 OÁCH 3 NO M r = 283.33 Triclinic, P1 a = 8.4690 (4) Å b = 9.0215 (4) Å c = 10.3137 (4) Å = 74.363 (3) = 83.630 (3) = 70.847 (3) V = 716.61 (5) Å 3 Z = 2 Mo K radiation = 0.09 mm À1 T = 120 (2) K 0.08 Â 0.06 Â 0.02 mm Data collection Bruker-Nonius 95mm CCD camera on -goniostat Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T min = 0.624, T max = 1 (expected range = 0.623-0.998) 16142 measured reflections 13441 independent reflections 7956 reflections with I > 2(I) R int = 0.106

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10,11-Dihydrocarbamazepine (form III)

Abstract: Key indicatorsSingle-crystal X-ray study T = 150 K Mean (C-C) = 0.003 Å R factor = 0.041 wR factor = 0.101 Data-to-parameter ratio = 12.6For details of how these key indicators were automatically derived from the article, see

Cited by 15 publications

References 7 publications

Crystal polymorphism in a carbamazepine derivative: Oxcarbazepine

Crystal polymorphism in a carbamazepine derivative: Oxcarbazepine

Polymorphism and Solvatomorphism 2007

10,11-Dihydrocarbamazepine–formamide solvate (1/1)

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