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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.


The two-dimensional hydrogen-bonded network structure of (I), which is equivalent to that of the isomorphous compound (II). Hydrogen bonds are shown as dashed lines and non-associative H-atoms have been omitted [for symmetry codes see Tables 1 ▶ and 2 ▶].
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fig4: The two-dimensional hydrogen-bonded network structure of (I), which is equivalent to that of the isomorphous compound (II). Hydrogen bonds are shown as dashed lines and non-associative H-atoms have been omitted [for symmetry codes see Tables 1 ▶ and 2 ▶].

Mentions: In the crystals of (I) and (II), two H atoms of the ammonium group give cyclic asymmetric three-centre (bifurcated) N—H⋯(O,O) hydrogen-bonding inter­actions with the anion (Tables 1 ▶ and 2 ▶, respectively). One of these is with two O-atom acceptors of the carboxyl group (O13, O14) [graph set (4)], the other is with the carboxyl and phen­oxy O-atom acceptors (O13ii, O11ii) of an inversion-related anion [graph set (5)]. These, together with a third N1—H13⋯O13ii hydrogen bond, give a cyclic (8) ring motif, forming a series of conjoined rings which extend the structures along c. The other H atom gives structure extension through an N—H⋯O hydrogen bond to a carboxyl O atom (O14iii), forming a two-dimensional sheet-like structure which lies parallel to (100). Present in the crystal are short inversion-related inter­molecular F4⋯F4iv contacts of 2.793 (2) Å [symmetry code: (iv) −x + 2, −y + 1, −z − 1]. The crystal packing and hydrogen-bonding in (I) is identical to that in isostructural (II), as shown in Fig. 4 ▶.


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)

The two-dimensional hydrogen-bonded network structure of (I), which is equivalent to that of the isomorphous compound (II). Hydrogen bonds are shown as dashed lines and non-associative H-atoms have been omitted [for symmetry codes see Tables 1 ▶ and 2 ▶].
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig4: The two-dimensional hydrogen-bonded network structure of (I), which is equivalent to that of the isomorphous compound (II). Hydrogen bonds are shown as dashed lines and non-associative H-atoms have been omitted [for symmetry codes see Tables 1 ▶ and 2 ▶].
Mentions: In the crystals of (I) and (II), two H atoms of the ammonium group give cyclic asymmetric three-centre (bifurcated) N—H⋯(O,O) hydrogen-bonding inter­actions with the anion (Tables 1 ▶ and 2 ▶, respectively). One of these is with two O-atom acceptors of the carboxyl group (O13, O14) [graph set (4)], the other is with the carboxyl and phen­oxy O-atom acceptors (O13ii, O11ii) of an inversion-related anion [graph set (5)]. These, together with a third N1—H13⋯O13ii hydrogen bond, give a cyclic (8) ring motif, forming a series of conjoined rings which extend the structures along c. The other H atom gives structure extension through an N—H⋯O hydrogen bond to a carboxyl O atom (O14iii), forming a two-dimensional sheet-like structure which lies parallel to (100). Present in the crystal are short inversion-related inter­molecular F4⋯F4iv contacts of 2.793 (2) Å [symmetry code: (iv) −x + 2, −y + 1, −z − 1]. The crystal packing and hydrogen-bonding in (I) is identical to that in isostructural (II), as shown in Fig. 4 ▶.

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.