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Location of the proton in the very strong OHO hydrogen bonds in 2-(N,N-diethylamino-N-oxymethyl)-4,6-dichlorophenol. A single crystal neutron diffraction study

Published/Copyright: July 28, 2010
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 212 Issue 2

Abstract

The crystal structure of 2-(N,N-diethylamino-N-oxymethyl)-4,6-dichlorophenol contains two slightly different molecules A and B, both with very strong intramolecular O … H … O hydrogen bonds, with O–O distances 2.423(4) Å and 2.400(5) Å, respectively, and with no crystallographic symmetry. The bridging oxygen atoms are also chemically different, O1 is bonded to carbon and O2 to nitrogen. The single crystal neutron diffraction study shows quite unambiguously that the proton in both cases is located slightly off-centred. In the A molecule O1–H = 1.167(6) Å, H–O2 = 1.258(6) Å and the angle O–H–O = 175.8(5)°; in the B molecule O1–H = 1.186(7) Å, H–O2 = 1.214(7) Å and the angle O–H–O = 176.5(5)°. As expected the proton is thus closer to the centre in the slightly shorter hydrogen bond.

Published Online: 2010-7-28
Published in Print: 1997-2-1

© 2015 Oldenbourg Wissenschaftsverlag GmbH, Rosenheimer Str. 145, 81671 München

Articles in the same Issue

  1. Single crystal neutron diffraction of decagonal Al72.5Co11Ni16.5
  2. A procedure for ab initio phasing of one-wavelength anomalous scattering data from proteins – combining direct methods with the solvent flattening technique
  3. A cosine transform approach to indexing
  4. Crystal structure of Cu12P20Br10, a polyphosphide containing a new phosphorus polymer
  5. Kommensurable Kompositstruktur des β-YbV4O81
  6. Über die Darstellung und die Kristallstruktur der Komplexverbindungen Ni(py)4F2 · 2H2O und Cu(py)4F2 · 1,33 HF · 2H2O
  7. Crystal structure and electrical property of (BEDT-TTF)5[Pt(SCN)4]
  8. Location of the proton in the very strong OHO hydrogen bonds in 2-(N,N-diethylamino-N-oxymethyl)-4,6-dichlorophenol. A single crystal neutron diffraction study
  9. Molecular cocrystals of carboxylic acids Part 24: cocrystals involving triphenylphosphine oxide: structures of the unique adduct hydrates of triphenylphosphine oxide with adamantane carboxylic acid and terephthalic acid, and the anhydrous adduct with o-phthalic acid1
  10. Redetermination of the crystal structure of strontium polyphosphate, [Sr2(PO3)4]
  11. Crystal structure of nickel lead selenide (3/2/2), Ni3Pb2Se2
  12. Crystal structure of neodymium platinum oxide (2/2/7), Nd2Pt2O7
  13. Crystal structure of dithulium trisulfide, Tm2S3-III
  14. Crystal structure of tris(mono-methylammonium)nonachlorodibismuthate(III), (CH3NH3)3Bi2Cl9
  15. Crystal structure of strontium catena-polyphosphate, [Sr(PO3)2]x
  16. Crystal structure of 6-[6-(6-amino-pyridine-2-yl)-hexyl]pyridine-2-ylamine, C16H22N4
  17. Crystal structure of 2-(2,5-dimethyl-pyrrol-1-yl)-phenylaminehemihydrate, C12H14N2 · 0.5 H2O
  18. Crystal structure of 9,10-bis(trimethylsiloxy)anthracene, C20H26O2Si2
  19. Crystal structure of 3-ethoxy-4-[(1′-ethyl-3′,3′-dimethylindoline-2′-ylidene)methyl]cyclobutene-1,2-dione, C19H21NO3
  20. Crystal structure of 4-(1′-ethyl-3′,3′-dimethylindoline-2′-ylidene)methyl-3-hydroxycyclobutene-1,2-dione, C17H17NO3
  21. Crystal structure of 3-ethoxy-4-[3′-ethyl-2(3H)benzothiazol-2′-ylidenemethyl]cyclobutene-1,2-dione, C16H15NO3S
  22. Crystal structure of 3,4-bis[(1′-ethyl-3′,3′-dimethylindoline-2′-ylidene)methyl]cyclobutene-1,2-dione, C30H32N2O2
  23. Crystal structure of 3a-methyl-7a-(trimethylsiloxy)-1-propenyl-octahydroinden-4-one, C16H28O2Si
  24. Crystal structure of 2,5a-dimethyl-3-trimethylsilyl-octahydro-1-oxa-cyclopenta[c]inden-6-one, C16H28O2Si
  25. Crystal structure of cis-bis(triphenylphosphine)platinum(II)-chloro-N-indazolate, PtCl[P(C6H5)3]2(C7H5N2)
  26. Crystal structure of but-2-en-1-yl-triphenylstannane, C22H22Sn
  27. Crystal structure of 9-(2,6-dimethoxyphenyl)-1,8-dimethoxyxanthylium chloride trihydrate, [C23H21O5]+Cl− · 3H2O
  28. Crystal structure of triphenylmethylphosphonium triiodoplumbate, (P(C6H5)3(CH3))(PbI3)
  29. Crystal structure of 2-benzyloxyphenylisocyanide, C14H11NO
  30. Crystal structure of bisimidazolium tetrachloropalladate(II), [C3H5N2]2[PdCl4]
  31. Crystal structure of tetrakis[3,4;3′,4′-bis(propylenedithio)-2,2′,5,5′-tetra thiafulvalenium] nonabromotrimercurate, (C12H12S8)4(Hg2Br6)HgBr3
  32. Crystal structure of N-p-tolyl-5-iodo-4-methyl-3a,4,5,7a-tetrahydro-5,7a-epoxyisoindoline, C16H18INO
  33. Crystal structure of (−)-(1R,4R,7S)-7-hydroxy-5-(p-toluenesulfonyl)-5-aza-2-oxabicyclo[2.2.1]heptane, C12H15NO4S
  34. Crystal structure of (−)-(5R,1S,2′S)-3-(1-O-benzyl-2,3-O-isopropylidene-1,2,3-dihydroxypropyl)-5-chloromethyl-4,5-dihydro-1,2-oxazole,C17H22NO4Cl
  35. Crystal structure of (−)-(4R,5R,1′S)-5-benzyloxy-4-methyl-3-(1-phenyl-ethyl)-tetrahydro-1,3-oxazine-2-one, C20H23NO3
  36. Crystal structure of trimethyl 2,3,5,6,7,8,9,10-octahydro-2,3-epoxy-benzocyclooctene-1,2,4-tricarboxylate, C18H22O7
https://doi.org/10.1524/zkri.1997.212.2.126

Articles in the same Issue

  1. Single crystal neutron diffraction of decagonal Al72.5Co11Ni16.5
  2. A procedure for ab initio phasing of one-wavelength anomalous scattering data from proteins – combining direct methods with the solvent flattening technique
  3. A cosine transform approach to indexing
  4. Crystal structure of Cu12P20Br10, a polyphosphide containing a new phosphorus polymer
  5. Kommensurable Kompositstruktur des β-YbV4O81
  6. Über die Darstellung und die Kristallstruktur der Komplexverbindungen Ni(py)4F2 · 2H2O und Cu(py)4F2 · 1,33 HF · 2H2O
  7. Crystal structure and electrical property of (BEDT-TTF)5[Pt(SCN)4]
  8. Location of the proton in the very strong OHO hydrogen bonds in 2-(N,N-diethylamino-N-oxymethyl)-4,6-dichlorophenol. A single crystal neutron diffraction study
  9. Molecular cocrystals of carboxylic acids Part 24: cocrystals involving triphenylphosphine oxide: structures of the unique adduct hydrates of triphenylphosphine oxide with adamantane carboxylic acid and terephthalic acid, and the anhydrous adduct with o-phthalic acid1
  10. Redetermination of the crystal structure of strontium polyphosphate, [Sr2(PO3)4]
  11. Crystal structure of nickel lead selenide (3/2/2), Ni3Pb2Se2
  12. Crystal structure of neodymium platinum oxide (2/2/7), Nd2Pt2O7
  13. Crystal structure of dithulium trisulfide, Tm2S3-III
  14. Crystal structure of tris(mono-methylammonium)nonachlorodibismuthate(III), (CH3NH3)3Bi2Cl9
  15. Crystal structure of strontium catena-polyphosphate, [Sr(PO3)2]x
  16. Crystal structure of 6-[6-(6-amino-pyridine-2-yl)-hexyl]pyridine-2-ylamine, C16H22N4
  17. Crystal structure of 2-(2,5-dimethyl-pyrrol-1-yl)-phenylaminehemihydrate, C12H14N2 · 0.5 H2O
  18. Crystal structure of 9,10-bis(trimethylsiloxy)anthracene, C20H26O2Si2
  19. Crystal structure of 3-ethoxy-4-[(1′-ethyl-3′,3′-dimethylindoline-2′-ylidene)methyl]cyclobutene-1,2-dione, C19H21NO3
  20. Crystal structure of 4-(1′-ethyl-3′,3′-dimethylindoline-2′-ylidene)methyl-3-hydroxycyclobutene-1,2-dione, C17H17NO3
  21. Crystal structure of 3-ethoxy-4-[3′-ethyl-2(3H)benzothiazol-2′-ylidenemethyl]cyclobutene-1,2-dione, C16H15NO3S
  22. Crystal structure of 3,4-bis[(1′-ethyl-3′,3′-dimethylindoline-2′-ylidene)methyl]cyclobutene-1,2-dione, C30H32N2O2
  23. Crystal structure of 3a-methyl-7a-(trimethylsiloxy)-1-propenyl-octahydroinden-4-one, C16H28O2Si
  24. Crystal structure of 2,5a-dimethyl-3-trimethylsilyl-octahydro-1-oxa-cyclopenta[c]inden-6-one, C16H28O2Si
  25. Crystal structure of cis-bis(triphenylphosphine)platinum(II)-chloro-N-indazolate, PtCl[P(C6H5)3]2(C7H5N2)
  26. Crystal structure of but-2-en-1-yl-triphenylstannane, C22H22Sn
  27. Crystal structure of 9-(2,6-dimethoxyphenyl)-1,8-dimethoxyxanthylium chloride trihydrate, [C23H21O5]+Cl− · 3H2O
  28. Crystal structure of triphenylmethylphosphonium triiodoplumbate, (P(C6H5)3(CH3))(PbI3)
  29. Crystal structure of 2-benzyloxyphenylisocyanide, C14H11NO
  30. Crystal structure of bisimidazolium tetrachloropalladate(II), [C3H5N2]2[PdCl4]
  31. Crystal structure of tetrakis[3,4;3′,4′-bis(propylenedithio)-2,2′,5,5′-tetra thiafulvalenium] nonabromotrimercurate, (C12H12S8)4(Hg2Br6)HgBr3
  32. Crystal structure of N-p-tolyl-5-iodo-4-methyl-3a,4,5,7a-tetrahydro-5,7a-epoxyisoindoline, C16H18INO
  33. Crystal structure of (−)-(1R,4R,7S)-7-hydroxy-5-(p-toluenesulfonyl)-5-aza-2-oxabicyclo[2.2.1]heptane, C12H15NO4S
  34. Crystal structure of (−)-(5R,1S,2′S)-3-(1-O-benzyl-2,3-O-isopropylidene-1,2,3-dihydroxypropyl)-5-chloromethyl-4,5-dihydro-1,2-oxazole,C17H22NO4Cl
  35. Crystal structure of (−)-(4R,5R,1′S)-5-benzyloxy-4-methyl-3-(1-phenyl-ethyl)-tetrahydro-1,3-oxazine-2-one, C20H23NO3
  36. Crystal structure of trimethyl 2,3,5,6,7,8,9,10-octahydro-2,3-epoxy-benzocyclooctene-1,2,4-tricarboxylate, C18H22O7
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