The Crystal Structure of Morphine Hydrate.

Bye, Erik; Johnson, I.; Bugge, Andreas; Hänninen, Osmo; Vialle, J.P.; Anthonsen, T.

doi:10.3891/acta.chem.scand.30b-0549

Cited by 42 publications

(37 citation statements)

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“…Except for a change of sign, torsion angles of two characteristic atomic sequences connecting N with the phenyl ring compare well with the values of morphine (Bye, 1976) Tollenaere et al (1979) give a mean value of 4.5 (1)A for these molecules.…”

supporting

confidence: 64%

“…close to 90.9 ° in morphine hydrochloride trihydrate (Gylbert, 1973), 86.6 ° in morphine hydrate (Bye, 1976) and 88.4 ° in codeine hydrobromide dihydrate (Kartha et al, 1962). The phenyl ring A of sinomenine is not strictly planar, atomic distances from the mean ring plane ranging from -0.016 [C(ll)] to +0.020A [C(12)].…”

mentioning

confidence: 95%

“…The phenyl ring A of sinomenine is not strictly planar, atomic distances from the mean ring plane ranging from -0.016 [C(ll)] to +0.020A [C(12)]. Significantly nonplanar phenyl rings were also found in morphine (Gylbert, 1973;Bye, 1976) and closely related compounds like codeine (Kartha et al, 1962), azidomorphine (Sasvfiri, Simon, Bogn/tr & Makleit, 1974), oxymorphone (Sime, Dobler & Sime, 1976a), naloxone (Karle, 1974) and nalbuphine (Sime, Dobler & Sime, 1976b), all possessing a 4,5 ether bridge. On the other hand, dextromethorphan with the same chirality as sinomenine and also devoid of the ether bridge has a strictly planar ring A (Gylbert & Carlstr6m, 1977).…”

mentioning

confidence: 99%

“…Corresponding values for ring B and D are respectively 0.1-1.1 and 0-63 °, 0.1-1.9 and 1.22 °. The largest discrepancies in the D rings are in the angles at C(15), C (16) and N. There is an exocyclic angular asymmetry at N in sinomenine presumably caused by two contacts (4) 120.7 (1) C(13)C(5)C(6) 112.2 (1) C(3)C(4)C (12) 120.9 (1) C(5)C(6)C (7) 116.4 (1) C(4)C(12)C (11) 117.5 (1) C(6)C (7) (13) (Bye, 1976). tX=C,N.…”

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confidence: 99%

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Structure of sinomenine hydrochloride dihydrate, C19H24NO4+.Cl−.2H2O

Bjørnevåg¹,

Hauback²,

Mo³

et al. 1983

Acta Crystallogr C

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Abstract. M r = 401. 89, m.p. 503-505 K, orthorhombic, P212,2~, a=19.256(8), b--14.326(5), c= 7.224 (3)/~,, Z= 4, V= 1992.8 (1.4) A 3, Dx= 1.339 Mg m -3. Diffractometer data were collected at 293.0 (5) K with Mo Kct radiation (2 = 0.71073 A) to a limit in (sin 0)/2= 0.65 A -~ and corrected for coincidence loss but not for absorption ~= 0.222 mm-~). The structure solution was initiated by the heavy-atom method with C1 positions determined from Harker sections. Least-squares refinement including H atoms converged at R=0.031 for 2512 F o. Refinement of both enantiomers suggests that the absolute configuration of sinomenine is opposite to that of natural (-)-morphine. The sinomenine molecule has the usual T shape common to morphine alkaloids. Strain in the A ring of these alkaloids gives rise to aplanar distortions; the directions of the principal atomic shifts apparently depend on whether a 4,5 ether bridge is present or not. Ring C in sinomenine adopts a half-chair conformation with five C atoms roughly coplanar. The torsion angles in the phenylethylamine chain are 9.0 and 81.4 ° compared to 0.2 and -93.2 ° , respectively, in morphine.

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supporting

confidence: 64%

mentioning

confidence: 95%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Structure of sinomenine hydrochloride dihydrate, C19H24NO4+.Cl−.2H2O

Bjørnevåg¹,

Hauback²,

Mo³

et al. 1983

Acta Crystallogr C

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“…In the free base the C(17)-N(1) bond length is 1.468(7) A. These shorter equivalent C-N bond lengths in the free ba2e are comparable to the average C-N bond length of 1.475 A expected for an unprotonated amino group (16).…”

Section: Molecular Structuresupporting

confidence: 50%

The crystal structure of free base cocaine, C₁₇H₂₁NO₄

Hrynchuk¹,

Barton²,

Robertson³

1983

Can. J. Chem.

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. Can. J. Chem. 61, 481 (1983).The crystal structure of free base cocaine has been determined in order to compare the conformation with that observed in its salts, and to clarify the powder pattern of the pure compound. Crystals of (-)-cocaine are monoclinic, space group P 2 , , a = 10.130(1), b = 9.866(2), c = 8.445(1) A, P = 106.92(1)", Z = 2, D, = 1.25 g cm-j. Data were collected with MoK, radiation on a modified Picker diffractometer using the NRCC diffractomcter control system. The structure was solved by direct methods and refined by least squares to final R and R,,, of 0.065 and 0.062 ( w = l / u 2 (F)) using the 1818 independent reflections with sin 8/X < 0.7048 and IFJ/u(~F() 5 3.0.The free base exists in a piperidine chair conformation similar to the methiodide salt and the hydrochloride salt. H!wever, the piperidine ring carbon-nitrogen bondso in the free base are shorter than those in the salts; 1.460(7) and 1.467(6) A in the free base compared to 1.55(2) and 1.5 l(2) A in the methiodide salt and 1.50(1) and 1.49(1) A in the hydrochloride salt. Further, the orientations of the benzoxy group and the methoxycarbonyl group, with respect to the piperidine rings, are significantly different from that common to both salts. The calculated powder diffraction pattern of (-)-cocaine showed that several previously reported weak lines in powder diffraction data for this alkaloid should not be present. On a dktermink la structure du cristal de la base libre cocaine dans le but de comparer sa conformation avec celle de ses sels et dans le but de clarifier le diagramme de poudre du composk pur. La base libre existe sous une conformation chaise de la pipkridine semblable au mkthiodure et au chlorhydra~e. Cependant les liaisons C-N du cycle pipkridine de la base libre sont plus courtes que celle des sels; 1,460(7) et 1,467(6) A dans la base libre comparCes 1,55(2) et 1,51(2) A pour le mkthiodure et 1,49(1) A pour le chlorhydrate. De plus, les orientations du groupe benzoxy et du groupe mkthoxycarbonyle par rapport au cycle de la pipkridine sont significativement diffkrentes de celles communes au deux sels. Le diagramme de diffraction de la poudre calculk pour la (-)-cocaine montre que plusieurs des lignes faibles rapportkes antkrieurement dans les donnkes de diffraction de poudre pour cet alcaloide ne devraient pas &tre prCsentes.[Traduit par le journal]

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