In:
Acta Crystallographica Section C Structural Chemistry, International Union of Crystallography (IUCr), Vol. 75, No. 3 ( 2019-03-01), p. 283-293
Abstract:
The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C 9 H 13 O 4 P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C 11 H 17 O 6 P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C 10 H 15 O 4 P, dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate, C 10 H 14 NO 6 P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C 21 H 20 NO 6 P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C 21 H 20 ClO 4 P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, C 22 H 23 O 4 P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C—OH...O=P chain-linked packing and the dimeric types of hydrogen-bond bridges of intermolecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper ( i.e. secondary graph sets of the C—H...O type) revealed a similarity in the graph-set descriptors, suggesting a fine interplay of substituent- and shape-dependent effects on strong–weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary Cα atom, but also by the nature and crowding of the ortho substituents of the α-aryl group.
Type of Medium:
Online Resource
ISSN:
2053-2296
DOI:
10.1107/S2053229619001839
DOI:
10.1107/S2053229619001839/ku3235sup1.cif
DOI:
10.1107/S2053229619001839/ku32351asup2.hkl
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10.1107/S2053229619001839/ku32351bsup3.hkl
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10.1107/S2053229619001839/ku32352asup4.hkl
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10.1107/S2053229619001839/ku32352bsup5.hkl
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10.1107/S2053229619001839/ku32353asup6.hkl
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10.1107/S2053229619001839/ku32353bsup7.hkl
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10.1107/S2053229619001839/ku32353csup8.hkl
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10.1107/S2053229619001839/ku3235sup9.pdf
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10.1107/S2053229619001839/ku32351asup10.cml
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10.1107/S2053229619001839/ku32351bsup11.cml
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10.1107/S2053229619001839/ku32352asup12.cml
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10.1107/S2053229619001839/ku32352bsup13.cml
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10.1107/S2053229619001839/ku32353asup14.cml
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10.1107/S2053229619001839/ku32353bsup15.cml
DOI:
10.1107/S2053229619001839/ku32353csup16.cml
Language:
Unknown
Publisher:
International Union of Crystallography (IUCr)
Publication Date:
2019
detail.hit.zdb_id:
2025703-X
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