Control and prediction of packing motifs: a rare occurrence of carbamazepine in a catemeric configuration

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

doi:10.1039/b610317k

Cited by 55 publications

(55 citation statements)

References 12 publications

(11 reference statements)

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“…Cruz-Cabeza et al (2007b) suggested that there was a kinetic disadvantage for carbamazepine to form strained hydrogen-bonding chains. Crystallizing carbamazepine with the closely related molecule dihydrocarbamazepine (XVIIb) led to a solid solution (Florence, Leech et al, 2006), which was isostructural with the catemeric dihydrocarbamazepine form II, showing carbamazepine could form the required hydrogen bonds. Finally, subliming carbamazepine onto a crystal of dihydrocarbamazepine form II led to the formation of the first crystals of carbamazepine form V, the targeted isostructural form (Arlin et al, 2011).…”

Section: Because the Right Crystallization Experiments Has Not Yet Beementioning

confidence: 99%

Why don't we find more polymorphs?

Price

2013

Acta Crystallogr B Struct Sci Cryst Eng Mater

199

232

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Printed in Singapore -all rights reservedCrystal structure prediction (CSP) studies are not limited to being a search for the most thermodynamically stable crystal structure, but play a valuable role in understanding polymorphism, as shown by interdisciplinary studies where the crystal energy landscape has been explored experimentally and computationally. CSP usually produces more thermodynamically plausible crystal structures than known polymorphs. This article illustrates some reasons why: because (i) of approximations in the calculations, particularly the neglect of thermal effects (see x1.1); (ii) of the molecular rearrangement during nucleation and growth (see x1.2); (iii) the solidstate structures observed show dynamic or static disorder, stacking faults, other defects or are not crystalline and so represent more than one calculated structure (see x1.3); (iv) the structures are metastable relative to other molecular compositions (see x1.4); (v) the right crystallization experiment has not yet been performed (see x1.5) or (vi) cannot be performed (see x1.6) and the possibility (vii) that the polymorphs are not detected or structurally characterized (see x1.7). Thus, we can only aspire to a general predictive theory for polymorphism, as this appears to require a quantitative understanding of the kinetic factors involved in all possible multi-component crystallizations. For a specific molecule, analysis of the crystal energy landscape shows the potential complexity of its crystallization behaviour.

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Section: Because the Right Crystallization Experiments Has Not Yet Beementioning

confidence: 99%

Why don't we find more polymorphs?

Price

2013

Acta Crystallogr B Struct Sci Cryst Eng Mater

199

232

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“…The anti-oriented N-H group is not utilized in the formation of the supramolecular complex thereby breaking Etter's first rule of hydrogen bonding which states 'all good proton donors and acceptors are used in hydrogen bonding' (Etter, 1990). More recently the preparation and structure determination of the computationally predicted Florence, Leech et al, 2006) catemeric Form V was achieved by using a seed crystal of the catemeric orthorhombic Form II of DHCBZ (Harrison et al, 2006) to template growth of a crystal of Form V of CBZ from the vapour phase (Arlin et al, 2011). In this example, the anti-oriented N-H group participates in the formation of the catemeric chain leaving the syn-oriented N-H donor uncoordinated.…”

Section: Introductionmentioning

confidence: 99%

Methanesulfonic acid salt forms of carbamazepine and 10,11-dihydrocarbamazepine

2013

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New methanesulfonic acid salt forms of the anticonvulsant and analgesic active pharmaceutical ingredient carbamazepine and its closely related structural analogue 10,11-dihydrocarbamazepine have been prepared and characterized by single-crystal X-ray diffraction at 120 and 100 K, respectively {namely [(5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H13N2O(+)·CH3SO3(-), and [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H15N2O(+)·CH3SO3(-)}. In light of the structural information obtained, the crystal structure of the carbamazepine trifluoroacetic acid monosolvate [dibenzo[b,f]azepine-5-carboxamide-trifluoroacetic acid (1/1), C15H12N2O·CF3COOH] was redetermined at 100 and 270 K, and from this data it was concluded that the protonation state for this solvate species is best described as in an `intermediate state' with the acidic proton located almost at the mid-point between the acid and base.

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“…This difference in molecular structure may explain why it has not been possible to form a 1-1 solid solution of CYH:DHC, whereas a solid solution of CBZ:DHC can be readily obtained via slow evaporation from ethylacetate solution. 20 Despite this difference in molecular structures, the targeted growth of CYH-III on DHC-II occurs highlighting the flexibility of the computationally assisted template induced crystallisation method.…”

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confidence: 99%

Isomorphous template induced crystallisation: a robust method for the targeted crystallisation of computationally predicted metastable polymorphs

et al. 2016

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A new method of inducing the crystallisation of metastable polymorphs by isomorphous templating has been developed and used to reproduce the crystallisation of CBZ-V on the surface of DHC-II. Studies of the growth of CBZ-V on DHC-II single crystals show crystals growing laterally and vertically on DHC-II surfaces without any significant face selectivity. The generality of this computationally inspired crystallisation approach is demonstrated by producing the first crystals of an entirely new polymorph of cyheptamide, which is isomorphous to both DHC-II and CBZ-V.

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Control and prediction of packing motifs: a rare occurrence of carbamazepine in a catemeric configuration

Abstract: A predicted orthorhombic crystal structure of carbamazepine is isostructural with an experimentally determined dihydrocarbamazepine crystal structure, providing a rationale for synthesising a novel 1 : 1 solid solution that has carbamazepine in a rare catemeric configuration

Cited by 55 publications

References 12 publications

Why don't we find more polymorphs?

Why don't we find more polymorphs?

Methanesulfonic acid salt forms of carbamazepine and 10,11-dihydrocarbamazepine

Isomorphous template induced crystallisation: a robust method for the targeted crystallisation of computationally predicted metastable polymorphs

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