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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

<a href="/cs/project/LM2015043" target="_blank" >LM2015043: Česká infrastruktura pro integrativní strukturní biologii</a><br>

Návaznosti

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

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Acta Crystallographica Section C: Structural Chemistry

ISSN

2053-2296

e-ISSN

—

Svazek periodika

76

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

13

Strana od-do

104-116

Kód UT WoS článku

000506846200013

EID výsledku v databázi Scopus

2-s2.0-85077700703