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Crystal structures and hydrogen bonding in the morpholinium salts of four phen-oxy-acetic acid analogues.

Smith G, Lynch DE - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The anhydrous salts morpholinium (tetra-hydro-2-H-1,4-oxazin-4-ium) phen-oxy-acetate, C4H10NO(+)·C8H7O3 (-), (I), morpholinium (4-fluoro-phen-oxy)acetate, C4H10NO(+)·C8H6 FO3 (-), (II), and isomeric morpholinium (3,5-di-chloro-phen-oxy)acetate (3,5-D), (III), and morpholinium (2,4-di-chloro-phen-oxy)acetic acid (2,4-D), C4H10NO(+)·C8H5Cl2O3 (-), (IV), have been determined and their hydrogen-bonded structures are described.With the structure of (II), the primary N-H⋯O inter-action is linear.With (IV), the ion pairs are linked though inversion-related N-H⋯O hydrogen bonds [graph set R 4 (2)(8)], giving a cyclic hetero-tetra-meric structure.

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

ABSTRACT
The anhydrous salts morpholinium (tetra-hydro-2-H-1,4-oxazin-4-ium) phen-oxy-acetate, C4H10NO(+)·C8H7O3 (-), (I), morpholinium (4-fluoro-phen-oxy)acetate, C4H10NO(+)·C8H6 FO3 (-), (II), and isomeric morpholinium (3,5-di-chloro-phen-oxy)acetate (3,5-D), (III), and morpholinium (2,4-di-chloro-phen-oxy)acetic acid (2,4-D), C4H10NO(+)·C8H5Cl2O3 (-), (IV), have been determined and their hydrogen-bonded structures are described. In the crystals of (I), (III) and (IV), one of the the aminium H atoms is involved in a three-centre asymmetric cation-anion N-H⋯O,O' R 1 (2)(4) hydrogen-bonding inter-action with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N-H⋯O inter-action is linear. In the structures of (I), (II) and (III), the second N-H⋯Ocarbox-yl hydrogen bond generates one-dimensional chain structures extending in all cases along [100]. With (IV), the ion pairs are linked though inversion-related N-H⋯O hydrogen bonds [graph set R 4 (2)(8)], giving a cyclic hetero-tetra-meric structure.

No MeSH data available.


The one-dimensional hydrogen-bonded polymeric structure of (II) extending along a. For symmetry codes, see Table 2 ▸.
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fig6: The one-dimensional hydrogen-bonded polymeric structure of (II) extending along a. For symmetry codes, see Table 2 ▸.

Mentions: The hydrogen-bonding extensions involving the second aminium H atom of the cation result in different structures in (I)–(III) compared to that in (IV). With (I)–(III), the primary heterodimers are all extended along a through an N1B—H⋯O14Ai hydrogen bond (Tables 1 ▸–3 ▸ ▸, respectively), into one-dimensional ribbon structures (Figs. 5 ▸–7 ▸ ▸). These ribbon structures provide further examples of the common hydrogen-bonded structure type found among the anhydrous aromatic morpholinium benzoate salts, e.g. with salicylic acid (Smith & Lynch, 2015b ▸) and with 2-chloro-4-nitro­benzoic acid (Ishida et al., 2001a ▸). In both of these examples, helical chains extend along 21screw axes in the crystals. Present also in structures of (I)–(IV) are minor weak inter-unit C—H⋯O inter­actions: in (I), C4A—H⋯O4Bii (Table 1 ▸); in (II), C4A—H⋯O4Bii; C6B—H⋯O13Aiii (Table 2 ▸): in (III), Cl2A—H⋯O13Aii (Table 3 ▸).


Crystal structures and hydrogen bonding in the morpholinium salts of four phen-oxy-acetic acid analogues.

Smith G, Lynch DE - Acta Crystallogr E Crystallogr Commun (2015)

The one-dimensional hydrogen-bonded polymeric structure of (II) extending along a. For symmetry codes, see Table 2 ▸.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645053&req=5

fig6: The one-dimensional hydrogen-bonded polymeric structure of (II) extending along a. For symmetry codes, see Table 2 ▸.
Mentions: The hydrogen-bonding extensions involving the second aminium H atom of the cation result in different structures in (I)–(III) compared to that in (IV). With (I)–(III), the primary heterodimers are all extended along a through an N1B—H⋯O14Ai hydrogen bond (Tables 1 ▸–3 ▸ ▸, respectively), into one-dimensional ribbon structures (Figs. 5 ▸–7 ▸ ▸). These ribbon structures provide further examples of the common hydrogen-bonded structure type found among the anhydrous aromatic morpholinium benzoate salts, e.g. with salicylic acid (Smith & Lynch, 2015b ▸) and with 2-chloro-4-nitro­benzoic acid (Ishida et al., 2001a ▸). In both of these examples, helical chains extend along 21screw axes in the crystals. Present also in structures of (I)–(IV) are minor weak inter-unit C—H⋯O inter­actions: in (I), C4A—H⋯O4Bii (Table 1 ▸); in (II), C4A—H⋯O4Bii; C6B—H⋯O13Aiii (Table 2 ▸): in (III), Cl2A—H⋯O13Aii (Table 3 ▸).

Bottom Line: The anhydrous salts morpholinium (tetra-hydro-2-H-1,4-oxazin-4-ium) phen-oxy-acetate, C4H10NO(+)·C8H7O3 (-), (I), morpholinium (4-fluoro-phen-oxy)acetate, C4H10NO(+)·C8H6 FO3 (-), (II), and isomeric morpholinium (3,5-di-chloro-phen-oxy)acetate (3,5-D), (III), and morpholinium (2,4-di-chloro-phen-oxy)acetic acid (2,4-D), C4H10NO(+)·C8H5Cl2O3 (-), (IV), have been determined and their hydrogen-bonded structures are described.With the structure of (II), the primary N-H⋯O inter-action is linear.With (IV), the ion pairs are linked though inversion-related N-H⋯O hydrogen bonds [graph set R 4 (2)(8)], giving a cyclic hetero-tetra-meric structure.

View Article: PubMed Central - HTML - PubMed

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

ABSTRACT
The anhydrous salts morpholinium (tetra-hydro-2-H-1,4-oxazin-4-ium) phen-oxy-acetate, C4H10NO(+)·C8H7O3 (-), (I), morpholinium (4-fluoro-phen-oxy)acetate, C4H10NO(+)·C8H6 FO3 (-), (II), and isomeric morpholinium (3,5-di-chloro-phen-oxy)acetate (3,5-D), (III), and morpholinium (2,4-di-chloro-phen-oxy)acetic acid (2,4-D), C4H10NO(+)·C8H5Cl2O3 (-), (IV), have been determined and their hydrogen-bonded structures are described. In the crystals of (I), (III) and (IV), one of the the aminium H atoms is involved in a three-centre asymmetric cation-anion N-H⋯O,O' R 1 (2)(4) hydrogen-bonding inter-action with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N-H⋯O inter-action is linear. In the structures of (I), (II) and (III), the second N-H⋯Ocarbox-yl hydrogen bond generates one-dimensional chain structures extending in all cases along [100]. With (IV), the ion pairs are linked though inversion-related N-H⋯O hydrogen bonds [graph set R 4 (2)(8)], giving a cyclic hetero-tetra-meric structure.

No MeSH data available.