X-ray diffraction and total 1H and 13C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine)

F. J. Martínez-Martínez; I. I. Padilla-Martínez; B. Hernández-Carlos; R. M. Pérez-Gutiérrez; E. V. García-Báez

doi:10.1023/A:1015656625468

X-ray diffraction and total ¹H and ¹³C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine)

F. J. Martínez-Martínez, I. I. Padilla-Martínez, B. Hernández-Carlos, R. M. Pérez-Gutiérrez, E. V. García-Báez

Research output: Contribution to journal › Article › peer-review

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Abstract

The X-ray diffraction structure of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine), isolated as an artifact from Bocconia Arborea, is reported. This compound crystallizes as orthorhombic system, space group Pna2₁, with a = 13.216(2) Å, b = 7.6547(10) Å, c = 20.096(3) Å. The phenanthridine central ring presents a distorted boat conformation, which gives rise to two planes with 21.30° between them. The acetonyl group at the six position forms weak C-H ⋯ O and C-H ⋯ π-ring interactions. The title compound was completely characterized in solution by ¹H and ¹³C and 2D NMR experiments.

Original language	English
Pages (from-to)	63-68
Number of pages	6
Journal	Journal of Chemical Crystallography
Volume	32
Issue number	3-4
DOIs	https://doi.org/10.1023/A:1015656625468
State	Published - 2002
Externally published	Yes

Keywords

(RS)-6-Acetonyldihydrochelerythrine
Hydrogen bond interactions
NMR
X-ray diffraction
π-interactions

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10.1023/A:1015656625468

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Martínez-Martínez, F. J., Padilla-Martínez, I. I., Hernández-Carlos, B., Pérez-Gutiérrez, R. M., & García-Báez, E. V. (2002). X-ray diffraction and total ¹H and ¹³C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine). Journal of Chemical Crystallography, 32(3-4), 63-68. https://doi.org/10.1023/A:1015656625468

@article{cb64294c12e64efb8bc7a86ee8bf4edd,

title = "X-ray diffraction and total 1H and 13C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine)",

abstract = "The X-ray diffraction structure of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine), isolated as an artifact from Bocconia Arborea, is reported. This compound crystallizes as orthorhombic system, space group Pna21, with a = 13.216(2) {\AA}, b = 7.6547(10) {\AA}, c = 20.096(3) {\AA}. The phenanthridine central ring presents a distorted boat conformation, which gives rise to two planes with 21.30° between them. The acetonyl group at the six position forms weak C-H ⋯ O and C-H ⋯ π-ring interactions. The title compound was completely characterized in solution by 1H and 13C and 2D NMR experiments.",

keywords = "(RS)-6-Acetonyldihydrochelerythrine, Hydrogen bond interactions, NMR, X-ray diffraction, π-interactions",

author = "Mart{\'i}nez-Mart{\'i}nez, {F. J.} and Padilla-Mart{\'i}nez, {I. I.} and B. Hern{\'a}ndez-Carlos and P{\'e}rez-Guti{\'e}rrez, {R. M.} and Garc{\'i}a-B{\'a}ez, {E. V.}",

note = "Funding Information: We thank Professor Herbert H{\"o}pfl for X-ray data collection and reviewers for their helpful advices. The first author also thanks CGPI (Project 200889) for financial support.",

year = "2002",

doi = "10.1023/A:1015656625468",

language = "Ingl{\'e}s",

volume = "32",

pages = "63--68",

journal = "Journal of Chemical Crystallography",

issn = "1074-1542",

number = "3-4",

}

Martínez-Martínez, FJ, Padilla-Martínez, II, Hernández-Carlos, B, Pérez-Gutiérrez, RM & García-Báez, EV 2002, 'X-ray diffraction and total ¹H and ¹³C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine)', Journal of Chemical Crystallography, vol. 32, no. 3-4, pp. 63-68. https://doi.org/10.1023/A:1015656625468

X-ray diffraction and total ¹H and ¹³C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine). / Martínez-Martínez, F. J.; Padilla-Martínez, I. I.; Hernández-Carlos, B. et al.
In: Journal of Chemical Crystallography, Vol. 32, No. 3-4, 2002, p. 63-68.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - X-ray diffraction and total 1H and 13C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine)

AU - Martínez-Martínez, F. J.

AU - Padilla-Martínez, I. I.

AU - Hernández-Carlos, B.

AU - Pérez-Gutiérrez, R. M.

AU - García-Báez, E. V.

N1 - Funding Information: We thank Professor Herbert Höpfl for X-ray data collection and reviewers for their helpful advices. The first author also thanks CGPI (Project 200889) for financial support.

PY - 2002

Y1 - 2002

N2 - The X-ray diffraction structure of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine), isolated as an artifact from Bocconia Arborea, is reported. This compound crystallizes as orthorhombic system, space group Pna21, with a = 13.216(2) Å, b = 7.6547(10) Å, c = 20.096(3) Å. The phenanthridine central ring presents a distorted boat conformation, which gives rise to two planes with 21.30° between them. The acetonyl group at the six position forms weak C-H ⋯ O and C-H ⋯ π-ring interactions. The title compound was completely characterized in solution by 1H and 13C and 2D NMR experiments.

AB - The X-ray diffraction structure of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine), isolated as an artifact from Bocconia Arborea, is reported. This compound crystallizes as orthorhombic system, space group Pna21, with a = 13.216(2) Å, b = 7.6547(10) Å, c = 20.096(3) Å. The phenanthridine central ring presents a distorted boat conformation, which gives rise to two planes with 21.30° between them. The acetonyl group at the six position forms weak C-H ⋯ O and C-H ⋯ π-ring interactions. The title compound was completely characterized in solution by 1H and 13C and 2D NMR experiments.

KW - (RS)-6-Acetonyldihydrochelerythrine

KW - Hydrogen bond interactions

KW - NMR

KW - X-ray diffraction

KW - π-interactions

UR - http://www.scopus.com/inward/record.url?scp=0036273125&partnerID=8YFLogxK

U2 - 10.1023/A:1015656625468

DO - 10.1023/A:1015656625468

M3 - Artículo

SN - 1074-1542

VL - 32

SP - 63

EP - 68

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

IS - 3-4

ER -

Martínez-Martínez FJ, Padilla-Martínez II, Hernández-Carlos B, Pérez-Gutiérrez RM , García-Báez EV. X-ray diffraction and total ¹H and ¹³C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine). Journal of Chemical Crystallography. 2002;32(3-4):63-68. doi: 10.1023/A:1015656625468

X-ray diffraction and total ¹H and ¹³C NMR assignment of (RS)-5,6-dihydro-7,8-dimethoxy-5-methyl-6-(2-oxopropyl)-(2, 3-methylenedioxyphenyl)-[c]-phenanthridine ((RS)-6-acetonyldihydrochelerythrine)

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Keywords

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