Nonisomorphous x-ray structures of tritylnitrile and tritylisonitrile

Kelsey M. Skodje; Lindsay M. Hinkle; Maria O. Miranda; Kent R. Mann; Daron E. Janzen

doi:10.1007/s10870-012-0345-2

Nonisomorphous x-ray structures of tritylnitrile and tritylisonitrile

Kelsey M. Skodje, Lindsay M. Hinkle, Maria O. Miranda, Kent R. Mann, Daron E. Janzen

Chemistry (Twin Cities)

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

7 Scopus citations

Abstract

The crystal structures of a related series of isosteric compounds, namely tritylnitrile 1, tritylisonitrile 2, and a solid solution of tritylnitrile/tritylisonitrile 3 have been determined by single crystal X-ray diffraction. The bond lengths, angles, and intermolecular interactions do not deviate significantly from previously reported nitriles and isonitriles. These isosteric compounds pack in nonisomorphous but very similar structures. Subtle differences between the packing of 1 and 2 are detailed. The solid solution of tritylnitrile/tritylisonitrile 3 is isomorphous with the structure of tritylnitrile 1. This solid solution possesses substitutional disorder involving the nitrile and isonitrile groups (Z′ = 2, nitrile/isonitrile occupancy ratios 53.7/46.3 and 54.6/45.4). The structure of tritylisonitrile 2 possesses positional disorder over two sites (Z′ = 2, occupancy ratio of 93.1/6.9). A comparison with previously reported nearly isosteric structures reveals that other chemically dissimilar compounds crystallize in each of the two molecular packing arrangements described in this report. Structure 1: monoclinic, P2 ₁/c, a = 18.049(11) Å, b = 9.583(6) Å, c = 17.824(11) Å, β = 108.680(10)°, V = 2921(3) Å ³, Z = 8, R ₁ = 0.0467, wR ₂ = 0.1491. Structure 2: triclinic, P, a = 9.5877(13) Å, b = 10.7479(14) Å, c = 14.809(2) Å, α = 88.457(2)°, β = 80.303(2)°, γ = 77.128(2)°, V = 1466.4(3) Å ³, Z = 4, R ₁ = 0.0423, wR ₂ = 0.1151. Structure 3: monoclinic, P2 ₁/c, a = 18.03464(15) Å, b = 9.5739(8) Å, c = 17.8251(11) Å, β = 108.5920(10)°, V = 2917.4(4) Å ³, Z = 8, R ₁ = 0.0587, wR ₂ = 0.1734.

Original language	English (US)
Pages (from-to)	972-980
Number of pages	9
Journal	Journal of Chemical Crystallography
Volume	42
Issue number	9
DOIs	https://doi.org/10.1007/s10870-012-0345-2
State	Published - Sep 2012

Bibliographical note

Funding Information:
Acknowledgments This work was supported by a 3M Faculty/ Student Collaborative Research Grant through the Center of Excellence for Women, Science and Technology, St. Catherine University. The authors thank Dr. Victor G. Young Jr., Director of the X-ray Crystallographic Laboratory of the Department of Chemistry, University of Minnesota, and Professor Doyle Britton of the Department of Chemistry, University of Minnesota for assistance.

Keywords

Isonitrile
Isosteric
Nitrile
Nonisomorphous
X-Ray crystallography

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10.1007/s10870-012-0345-2

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@article{89a9e7713ea54e9bb1d31f0666faf61d,

title = "Nonisomorphous x-ray structures of tritylnitrile and tritylisonitrile",

abstract = "The crystal structures of a related series of isosteric compounds, namely tritylnitrile 1, tritylisonitrile 2, and a solid solution of tritylnitrile/tritylisonitrile 3 have been determined by single crystal X-ray diffraction. The bond lengths, angles, and intermolecular interactions do not deviate significantly from previously reported nitriles and isonitriles. These isosteric compounds pack in nonisomorphous but very similar structures. Subtle differences between the packing of 1 and 2 are detailed. The solid solution of tritylnitrile/tritylisonitrile 3 is isomorphous with the structure of tritylnitrile 1. This solid solution possesses substitutional disorder involving the nitrile and isonitrile groups (Z′ = 2, nitrile/isonitrile occupancy ratios 53.7/46.3 and 54.6/45.4). The structure of tritylisonitrile 2 possesses positional disorder over two sites (Z′ = 2, occupancy ratio of 93.1/6.9). A comparison with previously reported nearly isosteric structures reveals that other chemically dissimilar compounds crystallize in each of the two molecular packing arrangements described in this report. Structure 1: monoclinic, P2 1/c, a = 18.049(11) {\AA}, b = 9.583(6) {\AA}, c = 17.824(11) {\AA}, β = 108.680(10)°, V = 2921(3) {\AA} 3, Z = 8, R 1 = 0.0467, wR 2 = 0.1491. Structure 2: triclinic, P, a = 9.5877(13) {\AA}, b = 10.7479(14) {\AA}, c = 14.809(2) {\AA}, α = 88.457(2)°, β = 80.303(2)°, γ = 77.128(2)°, V = 1466.4(3) {\AA} 3, Z = 4, R 1 = 0.0423, wR 2 = 0.1151. Structure 3: monoclinic, P2 1/c, a = 18.03464(15) {\AA}, b = 9.5739(8) {\AA}, c = 17.8251(11) {\AA}, β = 108.5920(10)°, V = 2917.4(4) {\AA} 3, Z = 8, R 1 = 0.0587, wR 2 = 0.1734.",

keywords = "Isonitrile, Isosteric, Nitrile, Nonisomorphous, X-Ray crystallography",

author = "Skodje, {Kelsey M.} and Hinkle, {Lindsay M.} and Miranda, {Maria O.} and Mann, {Kent R.} and Janzen, {Daron E.}",

note = "Funding Information: Acknowledgments This work was supported by a 3M Faculty/ Student Collaborative Research Grant through the Center of Excellence for Women, Science and Technology, St. Catherine University. The authors thank Dr. Victor G. Young Jr., Director of the X-ray Crystallographic Laboratory of the Department of Chemistry, University of Minnesota, and Professor Doyle Britton of the Department of Chemistry, University of Minnesota for assistance.",

year = "2012",

month = sep,

doi = "10.1007/s10870-012-0345-2",

language = "English (US)",

volume = "42",

pages = "972--980",

journal = "Journal of Chemical Crystallography",

issn = "1074-1542",

publisher = "Springer New York",

number = "9",

}

TY - JOUR

T1 - Nonisomorphous x-ray structures of tritylnitrile and tritylisonitrile

AU - Skodje, Kelsey M.

AU - Hinkle, Lindsay M.

AU - Miranda, Maria O.

AU - Mann, Kent R.

AU - Janzen, Daron E.

N1 - Funding Information: Acknowledgments This work was supported by a 3M Faculty/ Student Collaborative Research Grant through the Center of Excellence for Women, Science and Technology, St. Catherine University. The authors thank Dr. Victor G. Young Jr., Director of the X-ray Crystallographic Laboratory of the Department of Chemistry, University of Minnesota, and Professor Doyle Britton of the Department of Chemistry, University of Minnesota for assistance.

PY - 2012/9

Y1 - 2012/9

N2 - The crystal structures of a related series of isosteric compounds, namely tritylnitrile 1, tritylisonitrile 2, and a solid solution of tritylnitrile/tritylisonitrile 3 have been determined by single crystal X-ray diffraction. The bond lengths, angles, and intermolecular interactions do not deviate significantly from previously reported nitriles and isonitriles. These isosteric compounds pack in nonisomorphous but very similar structures. Subtle differences between the packing of 1 and 2 are detailed. The solid solution of tritylnitrile/tritylisonitrile 3 is isomorphous with the structure of tritylnitrile 1. This solid solution possesses substitutional disorder involving the nitrile and isonitrile groups (Z′ = 2, nitrile/isonitrile occupancy ratios 53.7/46.3 and 54.6/45.4). The structure of tritylisonitrile 2 possesses positional disorder over two sites (Z′ = 2, occupancy ratio of 93.1/6.9). A comparison with previously reported nearly isosteric structures reveals that other chemically dissimilar compounds crystallize in each of the two molecular packing arrangements described in this report. Structure 1: monoclinic, P2 1/c, a = 18.049(11) Å, b = 9.583(6) Å, c = 17.824(11) Å, β = 108.680(10)°, V = 2921(3) Å 3, Z = 8, R 1 = 0.0467, wR 2 = 0.1491. Structure 2: triclinic, P, a = 9.5877(13) Å, b = 10.7479(14) Å, c = 14.809(2) Å, α = 88.457(2)°, β = 80.303(2)°, γ = 77.128(2)°, V = 1466.4(3) Å 3, Z = 4, R 1 = 0.0423, wR 2 = 0.1151. Structure 3: monoclinic, P2 1/c, a = 18.03464(15) Å, b = 9.5739(8) Å, c = 17.8251(11) Å, β = 108.5920(10)°, V = 2917.4(4) Å 3, Z = 8, R 1 = 0.0587, wR 2 = 0.1734.

AB - The crystal structures of a related series of isosteric compounds, namely tritylnitrile 1, tritylisonitrile 2, and a solid solution of tritylnitrile/tritylisonitrile 3 have been determined by single crystal X-ray diffraction. The bond lengths, angles, and intermolecular interactions do not deviate significantly from previously reported nitriles and isonitriles. These isosteric compounds pack in nonisomorphous but very similar structures. Subtle differences between the packing of 1 and 2 are detailed. The solid solution of tritylnitrile/tritylisonitrile 3 is isomorphous with the structure of tritylnitrile 1. This solid solution possesses substitutional disorder involving the nitrile and isonitrile groups (Z′ = 2, nitrile/isonitrile occupancy ratios 53.7/46.3 and 54.6/45.4). The structure of tritylisonitrile 2 possesses positional disorder over two sites (Z′ = 2, occupancy ratio of 93.1/6.9). A comparison with previously reported nearly isosteric structures reveals that other chemically dissimilar compounds crystallize in each of the two molecular packing arrangements described in this report. Structure 1: monoclinic, P2 1/c, a = 18.049(11) Å, b = 9.583(6) Å, c = 17.824(11) Å, β = 108.680(10)°, V = 2921(3) Å 3, Z = 8, R 1 = 0.0467, wR 2 = 0.1491. Structure 2: triclinic, P, a = 9.5877(13) Å, b = 10.7479(14) Å, c = 14.809(2) Å, α = 88.457(2)°, β = 80.303(2)°, γ = 77.128(2)°, V = 1466.4(3) Å 3, Z = 4, R 1 = 0.0423, wR 2 = 0.1151. Structure 3: monoclinic, P2 1/c, a = 18.03464(15) Å, b = 9.5739(8) Å, c = 17.8251(11) Å, β = 108.5920(10)°, V = 2917.4(4) Å 3, Z = 8, R 1 = 0.0587, wR 2 = 0.1734.

KW - Isonitrile

KW - Isosteric

KW - Nitrile

KW - Nonisomorphous

KW - X-Ray crystallography

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U2 - 10.1007/s10870-012-0345-2

DO - 10.1007/s10870-012-0345-2

M3 - Article

AN - SCOPUS:84865509156

SN - 1074-1542

VL - 42

SP - 972

EP - 980

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

IS - 9

ER -

Nonisomorphous x-ray structures of tritylnitrile and tritylisonitrile

Abstract

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Keywords

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