Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate

Mohammed A. E. Shaibah; Hemmige S. Yathirajan; S. Madan Kumar; Kullaiah Byrappa; Christopher Glidewell

doi:10.1107/S2056989017012968

Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate

Mohammed A. E. Shaibah, Hemmige S. Yathirajan, S. Madan Kumar, Kullaiah Byrappa, Christopher Glidewell

School of Chemistry

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Abstract

The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine, C₂₁H₂₃NO₃ (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylammonium 2,4,6-trinitrophenolate (picrate), C₂₁H2₄NO₃⁺·C₆H₂N₃O₇^- (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N—H···(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—H···O hydrogen bonds to form sheets. Comparisons are made with some related structures.

Original language	English
Pages (from-to)	1488-1492
Number of pages	5
Journal	Acta Crystallographica Section E
Volume	73
Issue number	10
Early online date	15 Sept 2017
DOIs	https://doi.org/10.1107/S2056989017012968
Publication status	Published - Oct 2017

Keywords

Crystal structure
Disorder
Molecular conformation
Hydrogen bonding

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Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate (dataset)
Shaibah ( Mohammed A. E. Shaibah), M. A. E. (Creator), Yathirajan (Hemmige S. Yathirajan), H. S. (Creator), Kumar (S. Madan Kumar), S. M. (Creator), Byrappa, K. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 11 Sept 2017
https://dx.doi.org/10.5517/ccdc.csd.cc1pflb1 and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc1pfl90 (show fewer)
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Shaibah, M. A. E., Yathirajan, H. S., Kumar, S. M., Byrappa, K., & Glidewell, C. (2017). Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate. Acta Crystallographica Section E, 73(10), 1488-1492. https://doi.org/10.1107/S2056989017012968

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title = "Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate",

abstract = "The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylammonium 2,4,6-trinitrophenolate (picrate), C21H24NO3+·C6H2N3O7- (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N—H···(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—H···O hydrogen bonds to form sheets. Comparisons are made with some related structures.",

keywords = "Crystal structure, Disorder, Molecular conformation, Hydrogen bonding",

author = "Shaibah, {Mohammed A. E.} and Yathirajan, {Hemmige S.} and Kumar, {S. Madan} and Kullaiah Byrappa and Christopher Glidewell",

year = "2017",

month = oct,

doi = "10.1107/S2056989017012968",

language = "English",

volume = "73",

pages = "1488--1492",

journal = "Acta Crystallographica Section E",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "10",

}

Shaibah, MAE, Yathirajan, HS, Kumar, SM, Byrappa, K & Glidewell, C 2017, 'Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate', Acta Crystallographica Section E, vol. 73, no. 10, pp. 1488-1492. https://doi.org/10.1107/S2056989017012968

Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate. / Shaibah, Mohammed A. E.; Yathirajan, Hemmige S.; Kumar, S. Madan et al.
In: Acta Crystallographica Section E, Vol. 73, No. 10, 10.2017, p. 1488-1492.

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

TY - JOUR

T1 - Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate

AU - Shaibah, Mohammed A. E.

AU - Yathirajan, Hemmige S.

AU - Kumar, S. Madan

AU - Byrappa, Kullaiah

AU - Glidewell, Christopher

PY - 2017/10

Y1 - 2017/10

N2 - The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylammonium 2,4,6-trinitrophenolate (picrate), C21H24NO3+·C6H2N3O7- (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N—H···(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—H···O hydrogen bonds to form sheets. Comparisons are made with some related structures.

AB - The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylammonium 2,4,6-trinitrophenolate (picrate), C21H24NO3+·C6H2N3O7- (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N—H···(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—H···O hydrogen bonds to form sheets. Comparisons are made with some related structures.

KW - Crystal structure

KW - Disorder

KW - Molecular conformation

KW - Hydrogen bonding

U2 - 10.1107/S2056989017012968

DO - 10.1107/S2056989017012968

M3 - Article

SN - 2056-9890

VL - 73

SP - 1488

EP - 1492

JO - Acta Crystallographica Section E

JF - Acta Crystallographica Section E

IS - 10

ER -

Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate

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Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate (dataset)

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