Conformational flexibility in amido­phospho­esters: a CSD analysis com­pleted with two new crystal structures of (C6H5O)2P(O)X [X = NHC7H13 and N(CH2C6H5)2]

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F20%3A00117096" target="_blank" >RIV/00216224:14310/20:00117096 - isvavai.cz</a>

Result on the web

<a href="https://doi.org/10.1107/S2053229619016619" target="_blank" >https://doi.org/10.1107/S2053229619016619</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1107/S2053229619016619" target="_blank" >10.1107/S2053229619016619</a>

Result language

angličtina

Original language name

Conformational flexibility in amido­phospho­esters: a CSD analysis com­pleted with two new crystal structures of (C6H5O)2P(O)X [X = NHC7H13 and N(CH2C6H5)2]

Original language description

The crystal structures of diphenyl (cyclo­heptyl­amido)­phosphate, C19H24NO3P or (C6H5O)2P(O)(NHC7H13), (I), and diphenyl (di­benzyl­amido)­phosphate, C26H24NO3P or (C6H5O)2P(O)[N(CH2C6H5)2], (II), are reported. The NHC7H13 group in (I) provides two significant hydrogen-donor sites in N—H...O and C—H...O hydrogen bonds, needed for a one-dimensional hydrogen-bond pattern along [100] in the crystal, while (II), with a (C6H5CH2)2N moiety, lacks these hydrogen bonds, but its three-dimensional supra­molecular structure is mediated by C—H...π inter­actions. The conformational behaviour of the phenyl rings in (I), (II) and analogous structures from the Cambridge Structural Database (CSD) were studied in terms of flexibility, volume of the other group attached to phospho­rus and packing forces. From this study, synclinal (±sc), anti­clinal (±ac) and anti­periplanar (±ap) conformations were found to occur. In the structure of (II), there is an intra­molecular Cortho—H...O inter­action that imposes a +sc conformation for the phenyl ring involved. For the structures from the CSD, the +sc and ±ap conformations appear to be mainly imposed by similar Cortho—H...O intra­molecular inter­actions. The large contribution of the C...H/H...C contacts (32.3%) in the two-dimensional fingerprint plots of (II) is a result of the C—H...π inter­actions. The differential scanning calorimetry (DSC) analyses exhibit peak temperatures (Tm) at 109 and 81 °C for (I) and (II), respectively, which agree with the strengths of the inter­molecular contacts and the melting points.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10406 - Analytical chemistry

Project

<a href="/en/project/LM2015043" target="_blank" >LM2015043: Czech Infrastructure for Integrative Structural Biology</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2020

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Acta Crystallographica Section C: Structural Chemistry

ISSN

2053-2296

e-ISSN

—

Volume of the periodical

76

Issue of the periodical within the volume

1

Country of publishing house

GB - UNITED KINGDOM

Number of pages

13

Pages from-to

104-116

UT code for WoS article

000506846200013

EID of the result in the Scopus database

2-s2.0-85077700703