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Two-dimensional hydrogen-bonded polymers in the crystal structures of the ammonium salts of phen-oxy-acetic acid, (4-fluoro-phen-oxy)acetic acid and (4-chloro-2-methyl-phen-oxy)acetic acid.

Smith G - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: All have two-dimensional layered structures based on inter-species ammonium N-H⋯O hydrogen-bonding associations, which give core substructures consisting primarily of conjoined cyclic motifs.The crystals of (I) and (II) are isomorphous with the core comprising R 1 (2)(5), R 1 (2)(4) and centrosymmetric R 4 (2)(8) ring motifs, giving two-dimensional layers lying parallel to (100).No π-π ring associations are present in any of the structures.

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Affiliation: Science and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia.

ABSTRACT
The structures of the ammonium salts of phen-oxy-acetic acid, NH4 (+)·C8H6O3 (-), (I), (4-fluoro-phen-oxy)acetic acid, NH4 (+)·C8H5FO3 (-), (II), and the herbicidally active (4-chloro-2-methyl-phen-oxy)acetic acid (MCPA), NH4 (+)·C9H8ClO3 (-)·0.5H2O, (III) have been determined. All have two-dimensional layered structures based on inter-species ammonium N-H⋯O hydrogen-bonding associations, which give core substructures consisting primarily of conjoined cyclic motifs. The crystals of (I) and (II) are isomorphous with the core comprising R 1 (2)(5), R 1 (2)(4) and centrosymmetric R 4 (2)(8) ring motifs, giving two-dimensional layers lying parallel to (100). In (III), the water mol-ecule of solvation lies on a crystallographic twofold rotation axis and bridges two carboxyl O atoms in an R 4 (4)(12) hydrogen-bonded motif, creating two R 4 (3)(10) rings, which together with a conjoined centrosymmetric R 4 (2)(8) ring incorporating both ammonium cations, generate two-dimensional layers lying parallel to (100). No π-π ring associations are present in any of the structures.

No MeSH data available.


Mol­ecular conformation and atom labelling for (I), with inter-species hydrogen bonds shown as a dashed lines (see Table 1 ▶ for details). Non-H atoms are shown as 40% probability displacement ellipsoids.
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fig1: Mol­ecular conformation and atom labelling for (I), with inter-species hydrogen bonds shown as a dashed lines (see Table 1 ▶ for details). Non-H atoms are shown as 40% probability displacement ellipsoids.

Mentions: In the structures of the isomorphous ammonium phen­oxy­acetate (I) and (4-fluoro­phen­oxy)acetate (II) (Figs. 1 ▶ and 2 ▶, respectively), the anionic species are essentially planar; the comparative defining torsion angles in the phen­oxy­acetate side chain (C2—C1—O11—C12, C1—O11—C12—C13 and O11—C12—C13—O14) are 178.93 (19), −177.48 (18) and −173.58 (18)°, respectively, for (I) and −179.05 (18), −178.98 (17) and −174.13 (17)°, respectively, for (II). This planarity is also found in the MCPA anion in (III) (Fig. 3 ▶) where the corresponding torsion angles are −179.13 (15), −173.34 (14) and −178.71 (15)° and is also the case with the parent acids [for (I): Kennard et al. (1982 ▶), for (II): Smith et al. (1992 ▶) and for (III): Smith & Kennard (1981 ▶); Sieron et al. (2011 ▶)]. In (III), the water mol­ecule of solvation lies on a crystallographic twofold rotation axis.


Two-dimensional hydrogen-bonded polymers in the crystal structures of the ammonium salts of phen-oxy-acetic acid, (4-fluoro-phen-oxy)acetic acid and (4-chloro-2-methyl-phen-oxy)acetic acid.

Smith G - Acta Crystallogr Sect E Struct Rep Online (2014)

Mol­ecular conformation and atom labelling for (I), with inter-species hydrogen bonds shown as a dashed lines (see Table 1 ▶ for details). Non-H atoms are shown as 40% probability displacement ellipsoids.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257399&req=5

fig1: Mol­ecular conformation and atom labelling for (I), with inter-species hydrogen bonds shown as a dashed lines (see Table 1 ▶ for details). Non-H atoms are shown as 40% probability displacement ellipsoids.
Mentions: In the structures of the isomorphous ammonium phen­oxy­acetate (I) and (4-fluoro­phen­oxy)acetate (II) (Figs. 1 ▶ and 2 ▶, respectively), the anionic species are essentially planar; the comparative defining torsion angles in the phen­oxy­acetate side chain (C2—C1—O11—C12, C1—O11—C12—C13 and O11—C12—C13—O14) are 178.93 (19), −177.48 (18) and −173.58 (18)°, respectively, for (I) and −179.05 (18), −178.98 (17) and −174.13 (17)°, respectively, for (II). This planarity is also found in the MCPA anion in (III) (Fig. 3 ▶) where the corresponding torsion angles are −179.13 (15), −173.34 (14) and −178.71 (15)° and is also the case with the parent acids [for (I): Kennard et al. (1982 ▶), for (II): Smith et al. (1992 ▶) and for (III): Smith & Kennard (1981 ▶); Sieron et al. (2011 ▶)]. In (III), the water mol­ecule of solvation lies on a crystallographic twofold rotation axis.

Bottom Line: All have two-dimensional layered structures based on inter-species ammonium N-H⋯O hydrogen-bonding associations, which give core substructures consisting primarily of conjoined cyclic motifs.The crystals of (I) and (II) are isomorphous with the core comprising R 1 (2)(5), R 1 (2)(4) and centrosymmetric R 4 (2)(8) ring motifs, giving two-dimensional layers lying parallel to (100).No π-π ring associations are present in any of the structures.

View Article: PubMed Central - HTML - PubMed

Affiliation: Science and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia.

ABSTRACT
The structures of the ammonium salts of phen-oxy-acetic acid, NH4 (+)·C8H6O3 (-), (I), (4-fluoro-phen-oxy)acetic acid, NH4 (+)·C8H5FO3 (-), (II), and the herbicidally active (4-chloro-2-methyl-phen-oxy)acetic acid (MCPA), NH4 (+)·C9H8ClO3 (-)·0.5H2O, (III) have been determined. All have two-dimensional layered structures based on inter-species ammonium N-H⋯O hydrogen-bonding associations, which give core substructures consisting primarily of conjoined cyclic motifs. The crystals of (I) and (II) are isomorphous with the core comprising R 1 (2)(5), R 1 (2)(4) and centrosymmetric R 4 (2)(8) ring motifs, giving two-dimensional layers lying parallel to (100). In (III), the water mol-ecule of solvation lies on a crystallographic twofold rotation axis and bridges two carboxyl O atoms in an R 4 (4)(12) hydrogen-bonded motif, creating two R 4 (3)(10) rings, which together with a conjoined centrosymmetric R 4 (2)(8) ring incorporating both ammonium cations, generate two-dimensional layers lying parallel to (100). No π-π ring associations are present in any of the structures.

No MeSH data available.