Crystal and molecular structure of 4- methyl -4-p-nitro benzyl- 4- phosphoniatetracyclo [3.3.0.02,8.03,6]octane bromide

Mazhar-Ul-haque; Munawar Rashid; Sheldon E. Cremer

doi:10.1039/P29780001115

Crystal and molecular structure of 4- methyl -4-p-nitro benzyl- 4- phosphoniatetracyclo [3.3.0.0^2,8.0^3,6]octane bromide

Mazhar-Ul-haque^*, Munawar Rashid, Sheldon E. Cremer

^*Corresponding author for this work

King Fahd University of Petroleum & Minerals

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Crystals of the title compound are triclinic, space group PT, Z = 2, a = 6.750(3), b = 8.705(3), c = 12.961 (5) A,α= 91.60(3), β = 95.02(4), γ= 89.27(3)°. The structure was solved by the heavy-atom technique. and refinedby block-diagonal least-squares methods to R 0.056 for 1 440 independent reflections. The internal angles of thephosphetan ring are 87.3, 74.8, 87.5, and 90.3"; the ring is puckered with a dihedral angle of 46.6°. The crystalswere twinned, and the two twins were related by a two-fold rotation about a, which superimposed Okl and Okl.The twinning did not seriously limit the accuracy of the analysis.

Original language	English
Pages (from-to)	1115-1119
Number of pages	5
Journal	Journal of the Chemical Society. Perkin Transactions 2
DOIs	https://doi.org/10.1039/P29780001115
State	Published - 1978

Bibliographical note

Funding Information:
There are twelve intermolecular contacts G3.6 A (Table4), all of which are less than the sum of the van der Waals' radii. The X-ray structure confirms earlier assumptions as to the stereochemistry in the tetracyclic system.6 The material in the present study was prepared by reduction of the corresponding oxide (m.p. 156-157 "C) with trichlorosilane, followed by quaternization with @-nitro- benzyl bromide. The reduction step proceeded with overall inversion around the phosphorus and the quaternization reaction with retention. The bond distances and angles obtained from the current study will be useful for correlation of lanthanide- shift effects on 13C n.m.r. spectra. Initial studies of this kind on phosphetan oxides have been carried out.12 We thank Professor D. Rogers for advice and helpful discussions during the final stages of refinement, the Uni- versity of Petroleum and Minerals for a research grant (to M. U. H.), the staff of the Computer Center for their co-operation, and the Marquette University Committee on Research for financial support (to S. E. C.). [7/1369 Received, 27th July, 19771 la Chem. Soc. Special Publ., No. 18, 1965.

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1039/P29780001115

Cite this

@article{43350bd1ea9f488b99384e9428956784,

title = "Crystal and molecular structure of 4- methyl -4-p-nitro benzyl- 4- phosphoniatetracyclo [3.3.0.02,8.03,6]octane bromide",

abstract = "Crystals of the title compound are triclinic, space group PT, Z = 2, a = 6.750(3), b = 8.705(3), c = 12.961 (5) A,α= 91.60(3), β = 95.02(4), γ= 89.27(3)°. The structure was solved by the heavy-atom technique. and refinedby block-diagonal least-squares methods to R 0.056 for 1 440 independent reflections. The internal angles of thephosphetan ring are 87.3, 74.8, 87.5, and 90.3{"}; the ring is puckered with a dihedral angle of 46.6°. The crystalswere twinned, and the two twins were related by a two-fold rotation about a, which superimposed Okl and Okl.The twinning did not seriously limit the accuracy of the analysis.",

author = "Mazhar-Ul-haque and Munawar Rashid and Cremer, \{Sheldon E.\}",

note = "Funding Information: There are twelve intermolecular contacts G3.6 A (Table4), all of which are less than the sum of the van der Waals' radii. The X-ray structure confirms earlier assumptions as to the stereochemistry in the tetracyclic system.6 The material in the present study was prepared by reduction of the corresponding oxide (m.p. 156-157 {"}C) with trichlorosilane, followed by quaternization with @-nitro- benzyl bromide. The reduction step proceeded with overall inversion around the phosphorus and the quaternization reaction with retention. The bond distances and angles obtained from the current study will be useful for correlation of lanthanide- shift effects on 13C n.m.r. spectra. Initial studies of this kind on phosphetan oxides have been carried out.12 We thank Professor D. Rogers for advice and helpful discussions during the final stages of refinement, the Uni- versity of Petroleum and Minerals for a research grant (to M. U. H.), the staff of the Computer Center for their co-operation, and the Marquette University Committee on Research for financial support (to S. E. C.). [7/1369 Received, 27th July, 19771 la Chem. Soc. Special Publ., No. 18, 1965.",

year = "1978",

doi = "10.1039/P29780001115",

language = "English",

pages = "1115--1119",

journal = "Journal of the Chemical Society. Perkin Transactions 2",

issn = "0300-9580",

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TY - JOUR

T1 - Crystal and molecular structure of 4- methyl -4-p-nitro benzyl- 4- phosphoniatetracyclo [3.3.0.02,8.03,6]octane bromide

AU - Mazhar-Ul-haque,

AU - Rashid, Munawar

AU - Cremer, Sheldon E.

N1 - Funding Information: There are twelve intermolecular contacts G3.6 A (Table4), all of which are less than the sum of the van der Waals' radii. The X-ray structure confirms earlier assumptions as to the stereochemistry in the tetracyclic system.6 The material in the present study was prepared by reduction of the corresponding oxide (m.p. 156-157 "C) with trichlorosilane, followed by quaternization with @-nitro- benzyl bromide. The reduction step proceeded with overall inversion around the phosphorus and the quaternization reaction with retention. The bond distances and angles obtained from the current study will be useful for correlation of lanthanide- shift effects on 13C n.m.r. spectra. Initial studies of this kind on phosphetan oxides have been carried out.12 We thank Professor D. Rogers for advice and helpful discussions during the final stages of refinement, the Uni- versity of Petroleum and Minerals for a research grant (to M. U. H.), the staff of the Computer Center for their co-operation, and the Marquette University Committee on Research for financial support (to S. E. C.). [7/1369 Received, 27th July, 19771 la Chem. Soc. Special Publ., No. 18, 1965.

PY - 1978

Y1 - 1978

N2 - Crystals of the title compound are triclinic, space group PT, Z = 2, a = 6.750(3), b = 8.705(3), c = 12.961 (5) A,α= 91.60(3), β = 95.02(4), γ= 89.27(3)°. The structure was solved by the heavy-atom technique. and refinedby block-diagonal least-squares methods to R 0.056 for 1 440 independent reflections. The internal angles of thephosphetan ring are 87.3, 74.8, 87.5, and 90.3"; the ring is puckered with a dihedral angle of 46.6°. The crystalswere twinned, and the two twins were related by a two-fold rotation about a, which superimposed Okl and Okl.The twinning did not seriously limit the accuracy of the analysis.

AB - Crystals of the title compound are triclinic, space group PT, Z = 2, a = 6.750(3), b = 8.705(3), c = 12.961 (5) A,α= 91.60(3), β = 95.02(4), γ= 89.27(3)°. The structure was solved by the heavy-atom technique. and refinedby block-diagonal least-squares methods to R 0.056 for 1 440 independent reflections. The internal angles of thephosphetan ring are 87.3, 74.8, 87.5, and 90.3"; the ring is puckered with a dihedral angle of 46.6°. The crystalswere twinned, and the two twins were related by a two-fold rotation about a, which superimposed Okl and Okl.The twinning did not seriously limit the accuracy of the analysis.

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JO - Journal of the Chemical Society. Perkin Transactions 2

JF - Journal of the Chemical Society. Perkin Transactions 2

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