Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues
The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)acetic acid (2,4-D),...
Ausführliche Beschreibung
Autor*in: |
Graham Smith [verfasserIn] Daniel E. Lynch [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
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2015 |
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Übergeordnetes Werk: |
In: Acta Crystallographica Section E: Crystallographic Communications - International Union of Crystallography, 2015, 71(2015), 11, Seite 1392-1396 |
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Übergeordnetes Werk: |
volume:71 ; year:2015 ; number:11 ; pages:1392-1396 |
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DOI / URN: |
10.1107/S2056989015019842 |
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Katalog-ID: |
DOAJ087105365 |
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520 | |a The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. | ||
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10.1107/S2056989015019842 doi (DE-627)DOAJ087105365 (DE-599)DOAJ171923be3996414a95ba3ce1f5c28138 DE-627 ger DE-627 rakwb eng QD901-999 Graham Smith verfasserin aut Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. crystal structure morpholine salts phenoxyacetic acids herbicides 2,4-D 3,5-D hydrogen bonding Crystallography Daniel E. Lynch verfasserin aut In Acta Crystallographica Section E: Crystallographic Communications International Union of Crystallography, 2015 71(2015), 11, Seite 1392-1396 (DE-627)845400835 (DE-600)2843762-7 20569890 nnns volume:71 year:2015 number:11 pages:1392-1396 https://doi.org/10.1107/S2056989015019842 kostenfrei https://doaj.org/article/171923be3996414a95ba3ce1f5c28138 kostenfrei http://scripts.iucr.org/cgi-bin/paper?S2056989015019842 kostenfrei https://doaj.org/toc/2056-9890 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 71 2015 11 1392-1396 |
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10.1107/S2056989015019842 doi (DE-627)DOAJ087105365 (DE-599)DOAJ171923be3996414a95ba3ce1f5c28138 DE-627 ger DE-627 rakwb eng QD901-999 Graham Smith verfasserin aut Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. crystal structure morpholine salts phenoxyacetic acids herbicides 2,4-D 3,5-D hydrogen bonding Crystallography Daniel E. Lynch verfasserin aut In Acta Crystallographica Section E: Crystallographic Communications International Union of Crystallography, 2015 71(2015), 11, Seite 1392-1396 (DE-627)845400835 (DE-600)2843762-7 20569890 nnns volume:71 year:2015 number:11 pages:1392-1396 https://doi.org/10.1107/S2056989015019842 kostenfrei https://doaj.org/article/171923be3996414a95ba3ce1f5c28138 kostenfrei http://scripts.iucr.org/cgi-bin/paper?S2056989015019842 kostenfrei https://doaj.org/toc/2056-9890 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 71 2015 11 1392-1396 |
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10.1107/S2056989015019842 doi (DE-627)DOAJ087105365 (DE-599)DOAJ171923be3996414a95ba3ce1f5c28138 DE-627 ger DE-627 rakwb eng QD901-999 Graham Smith verfasserin aut Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. crystal structure morpholine salts phenoxyacetic acids herbicides 2,4-D 3,5-D hydrogen bonding Crystallography Daniel E. Lynch verfasserin aut In Acta Crystallographica Section E: Crystallographic Communications International Union of Crystallography, 2015 71(2015), 11, Seite 1392-1396 (DE-627)845400835 (DE-600)2843762-7 20569890 nnns volume:71 year:2015 number:11 pages:1392-1396 https://doi.org/10.1107/S2056989015019842 kostenfrei https://doaj.org/article/171923be3996414a95ba3ce1f5c28138 kostenfrei http://scripts.iucr.org/cgi-bin/paper?S2056989015019842 kostenfrei https://doaj.org/toc/2056-9890 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 71 2015 11 1392-1396 |
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10.1107/S2056989015019842 doi (DE-627)DOAJ087105365 (DE-599)DOAJ171923be3996414a95ba3ce1f5c28138 DE-627 ger DE-627 rakwb eng QD901-999 Graham Smith verfasserin aut Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. crystal structure morpholine salts phenoxyacetic acids herbicides 2,4-D 3,5-D hydrogen bonding Crystallography Daniel E. Lynch verfasserin aut In Acta Crystallographica Section E: Crystallographic Communications International Union of Crystallography, 2015 71(2015), 11, Seite 1392-1396 (DE-627)845400835 (DE-600)2843762-7 20569890 nnns volume:71 year:2015 number:11 pages:1392-1396 https://doi.org/10.1107/S2056989015019842 kostenfrei https://doaj.org/article/171923be3996414a95ba3ce1f5c28138 kostenfrei http://scripts.iucr.org/cgi-bin/paper?S2056989015019842 kostenfrei https://doaj.org/toc/2056-9890 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 71 2015 11 1392-1396 |
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10.1107/S2056989015019842 doi (DE-627)DOAJ087105365 (DE-599)DOAJ171923be3996414a95ba3ce1f5c28138 DE-627 ger DE-627 rakwb eng QD901-999 Graham Smith verfasserin aut Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. crystal structure morpholine salts phenoxyacetic acids herbicides 2,4-D 3,5-D hydrogen bonding Crystallography Daniel E. Lynch verfasserin aut In Acta Crystallographica Section E: Crystallographic Communications International Union of Crystallography, 2015 71(2015), 11, Seite 1392-1396 (DE-627)845400835 (DE-600)2843762-7 20569890 nnns volume:71 year:2015 number:11 pages:1392-1396 https://doi.org/10.1107/S2056989015019842 kostenfrei https://doaj.org/article/171923be3996414a95ba3ce1f5c28138 kostenfrei http://scripts.iucr.org/cgi-bin/paper?S2056989015019842 kostenfrei https://doaj.org/toc/2056-9890 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 71 2015 11 1392-1396 |
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QD901-999 Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues crystal structure morpholine salts phenoxyacetic acids herbicides 2,4-D 3,5-D hydrogen bonding |
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Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues |
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crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues |
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Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues |
abstract |
The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. |
abstractGer |
The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. |
abstract_unstemmed |
The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazin-4-ium) phenoxyacetate, C4H10NO+·C8H7O3−, (I), morpholinium (4-fluorophenoxy)acetate, C4H10NO+·C8H6 FO3−, (II), and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D), (III), and morpholinium (2,4-dichlorophenoxy)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′ R12(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N—H...O interaction is linear. In the structures of (I), (II) and (III), the second N—H...Ocarboxyl 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 R42(8)], giving a cyclic heterotetrameric structure. |
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Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues |
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