Bis[(2,2-dimethylpropanoyloxy)methyl] {[2-(6-amino-9H-purin-9-yl)eth-oxy] methyl}phosphonate-succinic acid (2/1)

Sungyup Jung; Jeong Myeong Ha; Il Won Kim

doi:10.1107/S1600536812006873

Bis[(2,2-dimethylpropanoyloxy)methyl] {[2-(6-amino-9H-purin-9-yl)eth-oxy] methyl}phosphonate-succinic acid (2/1)

Sungyup Jung, Jeong Myeong Ha, Il Won Kim

Department of Environmental Engineering

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

7 Scopus citations

Abstract

The title compound, C ₂₀H ₃₂N ₅O ₈P·0.5C ₄H ₆O ₄, is composed of two 9-{2-[bis-(pivaloyloxymeth-oxy)phosphinylmeth-oxy]eth-yl}adenine, commonly known as adefovir dipivoxil (AD), mol-ecules linked to the carb-oxy-lic acid groups of succinic acid (SA). The asymmetric unit contains one mol-ecule of AD and half a mol-ecule of SA, which sits on an inversion center. Both adenine units in the two AD mol-ecules make AD-SA N - H⋯O and SA-AD O - H⋯N hydrogen bonds to SA. In addition, the inter-molecular AD-AD N - H⋯O - P hydrogen bond serves to stabilize the cocrystal. There is also a π-π stacking inter-action [inter-planar spacing 3.34 (19) Å] between adjacent inversion-related adenine groups.

Original language	English
Pages (from-to)	o809-o810
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	68
Issue number	3
DOIs	https://doi.org/10.1107/S1600536812006873
State	Published - Mar 2012

Keywords

data-to-parameter ratio = 17.3
mean σ(C-C) = 0.004 Å
R factor = 0.046
single-crystal X-ray study
T = 296 K
wR factor = 0.143

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@article{118c5152f86342be95ed611b25496387,

title = "Bis[(2,2-dimethylpropanoyloxy)methyl] {[2-(6-amino-9H-purin-9-yl)eth-oxy] methyl}phosphonate-succinic acid (2/1)",

abstract = "The title compound, C 20H 32N 5O 8P·0.5C 4H 6O 4, is composed of two 9-{2-[bis-(pivaloyloxymeth-oxy)phosphinylmeth-oxy]eth-yl}adenine, commonly known as adefovir dipivoxil (AD), mol-ecules linked to the carb-oxy-lic acid groups of succinic acid (SA). The asymmetric unit contains one mol-ecule of AD and half a mol-ecule of SA, which sits on an inversion center. Both adenine units in the two AD mol-ecules make AD-SA N - H⋯O and SA-AD O - H⋯N hydrogen bonds to SA. In addition, the inter-molecular AD-AD N - H⋯O - P hydrogen bond serves to stabilize the cocrystal. There is also a π-π stacking inter-action [inter-planar spacing 3.34 (19) {\AA}] between adjacent inversion-related adenine groups.",

keywords = "data-to-parameter ratio = 17.3, mean σ(C-C) = 0.004 {\AA}, R factor = 0.046, single-crystal X-ray study, T = 296 K, wR factor = 0.143",

author = "Sungyup Jung and Ha, {Jeong Myeong} and Kim, {Il Won}",

year = "2012",

month = mar,

doi = "10.1107/S1600536812006873",

language = "English",

volume = "68",

pages = "o809--o810",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "3",

}

TY - JOUR

T1 - Bis[(2,2-dimethylpropanoyloxy)methyl] {[2-(6-amino-9H-purin-9-yl)eth-oxy] methyl}phosphonate-succinic acid (2/1)

AU - Jung, Sungyup

AU - Ha, Jeong Myeong

AU - Kim, Il Won

PY - 2012/3

Y1 - 2012/3

N2 - The title compound, C 20H 32N 5O 8P·0.5C 4H 6O 4, is composed of two 9-{2-[bis-(pivaloyloxymeth-oxy)phosphinylmeth-oxy]eth-yl}adenine, commonly known as adefovir dipivoxil (AD), mol-ecules linked to the carb-oxy-lic acid groups of succinic acid (SA). The asymmetric unit contains one mol-ecule of AD and half a mol-ecule of SA, which sits on an inversion center. Both adenine units in the two AD mol-ecules make AD-SA N - H⋯O and SA-AD O - H⋯N hydrogen bonds to SA. In addition, the inter-molecular AD-AD N - H⋯O - P hydrogen bond serves to stabilize the cocrystal. There is also a π-π stacking inter-action [inter-planar spacing 3.34 (19) Å] between adjacent inversion-related adenine groups.

AB - The title compound, C 20H 32N 5O 8P·0.5C 4H 6O 4, is composed of two 9-{2-[bis-(pivaloyloxymeth-oxy)phosphinylmeth-oxy]eth-yl}adenine, commonly known as adefovir dipivoxil (AD), mol-ecules linked to the carb-oxy-lic acid groups of succinic acid (SA). The asymmetric unit contains one mol-ecule of AD and half a mol-ecule of SA, which sits on an inversion center. Both adenine units in the two AD mol-ecules make AD-SA N - H⋯O and SA-AD O - H⋯N hydrogen bonds to SA. In addition, the inter-molecular AD-AD N - H⋯O - P hydrogen bond serves to stabilize the cocrystal. There is also a π-π stacking inter-action [inter-planar spacing 3.34 (19) Å] between adjacent inversion-related adenine groups.

KW - data-to-parameter ratio = 17.3

KW - mean σ(C-C) = 0.004 Å

KW - R factor = 0.046

KW - single-crystal X-ray study

KW - T = 296 K

KW - wR factor = 0.143

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U2 - 10.1107/S1600536812006873

DO - 10.1107/S1600536812006873

M3 - Article

AN - SCOPUS:84857954565

SN - 1600-5368

VL - 68

SP - o809-o810

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 3

ER -

Bis[(2,2-dimethylpropanoyloxy)methyl] {[2-(6-amino-9H-purin-9-yl)eth-oxy] methyl}phosphonate-succinic acid (2/1)

Abstract

Keywords

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