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Nonisomorphous X-Ray Structures of Tritylnitrile and Tritylisonitrile

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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, P21/c, a = 18.049(11) Å, b = 9.583(6) Å, c = 17.824(11) Å, β = 108.680(10)°, V = 2921(3) Å3, Z = 8, R 1 = 0.0467, wR 2 = 0.1491. Structure 2: triclinic, P \( \overline{1} \), 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) Å3, Z = 4, R 1 = 0.0423, wR 2 = 0.1151. Structure 3: monoclinic, P21/c, a = 18.03464(15) Å, b = 9.5739(8) Å, c = 17.8251(11) Å, β = 108.5920(10)°, V = 2917.4(4) Å3, Z = 8, R 1 = 0.0587, wR 2 = 0.1734.

Graphical Abstract

The crystal structures of the isosteric pair tritylnitrile 1 and tritylisonitrile 2 are nonisomorphous while the structure of a solid solution of tritylnitrile/tritylisonitrile 3 is isomorphous with the structure of tritylnitrile 1.

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Notes

  1. Isomorphous nitrile/isonitrile pairs with CCDC refcodes: 2,4,6-trimethylphenyl isocyanide (MOPJUW) [23], 2,4,6-trimethylcyanobenzene (MESITN) [24], p-decylphenyl isocyanide and p-decylphenylnitrile (EVOSEN and EVOSIR) [16], p-isocyanoaniline (LEGROE) [20], p-cyanoaniline (BERTOH) [25], 4-iodophenylisonitrile (IBZICN) [26], 4-iodobenzonitrile (IOBNIT) [27], pentafluorophenylisonitrile (KUMXOF) [28], pentafluorobenzonitrile (HUFVEJ) [29], trifluorovinylisocyanide and trifluoroacrylonitrile (MELFOY and MELFIS) [21].

  2. Nonisomorphous nitrile/isonitrile pairs with CCDC refcodes: 2,4,6-tribromobenzonisonitrile (TBZINT) [19], 2,4,6-tribromobenzonitrile (BRBZNT) [30], 4-bromobenzoisonitrile (BBIZCN) [26], 4-bromobenzonitrile (BRBNIT) [31], 2,6-xylylisocyanide (EBONAK) [32], 2,6-dimethylbenzonitrile (JIBDON) [33], p-nitrophenylisocyanide (EVOSAJ) [34], p-nitrobenzonitrile (PNBZNT) [35], 2,4,6-trichlorophenylisonitrile and 2,4,6-trichlorobenzonitrile (FUGVAE and CLBECN03) [18].

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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.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, St. Catherine University, 2004 Randolph Avenue, St. Paul, MN, 55105, USA

    Kelsey M. Skodje & Daron E. Janzen

  2. Department of Chemistry, University of Minnesota, 207 Pleasant St. SE, Minneapolis, MN, 55455, USA

    Lindsay M. Hinkle, Maria O. Miranda & Kent R. Mann

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  1. Kelsey M. Skodje
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  2. Lindsay M. Hinkle
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Correspondence to Daron E. Janzen.

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Skodje, K.M., Hinkle, L.M., Miranda, M.O. et al. Nonisomorphous X-Ray Structures of Tritylnitrile and Tritylisonitrile. J Chem Crystallogr 42, 972–980 (2012). https://doi.org/10.1007/s10870-012-0345-2

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