<i>ORTEX</i>2.1 – a 1677-atom version of<i>ORTEP</i>with automatic cell outline and cell packing for use on a PC

McArdle, Patrick

doi:10.1107/s002188989400230x

Cited by 118 publications

(57 citation statements)

References 4 publications

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“…Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993). Molecular graphics: ORTEX2.1 (McArdle, 1994). Software used to prepare material for publication: PARST (Nardelli, 1983).…”

Section: Methodsmentioning

confidence: 99%

(+)-(S)-1-{4-[(2-Benzothiazolyl)(methyl)amino]piperidyl}-3-(3,4-difluorophenoxy)-2-propanol (Lubeluzole)

Peeters¹,

Blaton²,

Ranter³

1995

Acta Crystallogr C

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The crystal structure and absolute configuration of the (+) enantiomer of the title compound, C22H25F2N3025, have been determined. The absolute configuration is S. The asymmetric unit contains two molecules having different conformations of the chain bridging the piperidyl and difluorophenyl rings. In one molecule the bridge is folded, while in the other it is fully extended. CommentLubeluzole, (I), is the (+) enantiomer of a novel benzothiazole compound proposed for use in the acute treatment of ischemic stroke. Lubeluzole reduces infarct size, accelerates recovery of tissue in the penumbra and potently protects neurologic function when administered intravenously following neocortial infarcts in rats. In contrast, the (-) isomer of lubeluzole is virtually inactive with respect to this model (De Ryck, Keersmaekers, Clincke, Janssen & Van Reet, 1994). /=', 7", c, %s--r"_'_% F (I)In order to determine the absolute configuration of lubeluzole, its crystal structure was solved. The asymmetric unit contains two molecules and corresponding bond lengths and angles within these molecules do not deviate significantly from each other or from those listed by Allen et al. (1987) ExperimentalCrystal data Selected geometric parameters (/~, o) CIA I----C2A 1 1.398 (5) C 1B----C2B CIA 1----C6A 1 1.385 (5) C 1B---436B C2A I---C3A 1 1.371 (6) C2B----C3B C3A I---C4A 1 1.345 (6) C3B----C4B C3A i--F7A 1 1.357 (4) C3B--F7B C4A 1----C5A 1 1.370 (5) C4B--C5B C4A I--F8A 1 1.342 (4) C4B--F8B C5A 1--426A 1 1.358 (5) C5B---C6B C6A 1---4)9A1.375 (3) C6B---O9B C 1A2----C2A2 1.37 (1) CIA2---C6A21.36 (1) C2A2---C3A21.34 ( 1 ) C2A2--F8A21.35 (1) C3A2--C4A2 1.37 (1)1.386 (4) C29B----C30B Molecule A shows rotational disorder of the difluorophenyl moiety. The atoms were split and refined using the SAME, DELU and SIMU restraint facilities of SHELXL93 (Sheldrick, 1993). The sum of the occupancy factors was constrained to 1. The occupancy factor for atoms C1A1-F8A1 refined to 0.732 (2). H atoms were calculated in geometrical positions and allowed to ride on their parent atom. Data collection: XSCANS (Siemens, 1993). Cell refinement: XSCANS. Data reduction: XSCANS. Program(s) used to solve structure: DIRDIF . Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993). Molecular graphics: ORTEX2.1 (McArdle, 1994). Software used to prepare material for publication: PARST (Nardelli, 1983).The authors thank Dr J. Tollenaere of the Janssen Research Foundation (Beerse, Belgium) for providing a sample of lubeluzole.Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., GarciaGranda, S., Gould, R. O., Smits, J. M.

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“…Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993). Molecular graphics: ORTEX2.1 (McArdle, 1994). Software used to prepare material for publication: PARST (Nardelli, 1983).…”

Section: Methodsmentioning

confidence: 99%

(+)-(S)-1-{4-[(2-Benzothiazolyl)(methyl)amino]piperidyl}-3-(3,4-difluorophenoxy)-2-propanol (Lubeluzole)

Peeters¹,

Blaton²,

Ranter³

1995

Acta Crystallogr C

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“…Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993). Molecular graphics: ORTEX2.1 (McArdle, 1994). Software used to prepare material for publication: PARST (Nardelli, 1983a).…”

Section: (1)mentioning

confidence: 99%

4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidinium Hydrogen Malate

Peeters¹,

Blaton²,

Ranter³

1995

Acta Crystallogr C

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“…I. The structure of the title compound showing the labelling of the atoms and displacement ellipsoids at the 50% probability level for non-H atoms (ORTEX; McArdle, 1994). H atoms have been omitted for clarity.…”

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confidence: 99%

Bis(μ-diethyldithiocarbamato)-1κS,1:2κ2S';2κS,1:2κ2S'-bis(ethylzinc)

Malik¹,

O’Brien²,

Motevalli³

1996

Acta Crystallogr C

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ORTEX2.1 – a 1677-atom version ofORTEPwith automatic cell outline and cell packing for use on a PC

Cited by 118 publications

References 4 publications

(+)-(S)-1-{4-[(2-Benzothiazolyl)(methyl)amino]piperidyl}-3-(3,4-difluorophenoxy)-2-propanol (Lubeluzole)

(+)-(S)-1-{4-[(2-Benzothiazolyl)(methyl)amino]piperidyl}-3-(3,4-difluorophenoxy)-2-propanol (Lubeluzole)

4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidinium Hydrogen Malate

Bis(μ-diethyldithiocarbamato)-1κS,1:2κ2S';2κS,1:2κ2S'-bis(ethylzinc)

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