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Volumn 8, Issue 9, 2008, Pages 3257-3270

Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid

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EID: 61549092473     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg701240m     Document Type: Article
Times cited : (6)

References (61)
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    • Braga, D.; Grepioni, F. Crystal Engineering, In Kirk-Othmer Encyclopedia of Chemical Technology, 5th ed.; Wiley: New York, 2004, Vol. 8, pp 65-94.
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    • The pentacyclic core of 1 is minimally flexible about the two cyclopentene hinges of the indane units and the central piperazinedione ring
    • The pentacyclic core of 1 is minimally flexible about the two cyclopentene "hinges" of the indane units and the central piperazinedione ring.
  • 18
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    • In October, 2007, 109 nonionic piperazinediones with 3D coordinates were retrieved from the Cambridge Structural Database (CSD, version 5.27 plus three updates; see (a) Allen, F. H. Acta Crystallogr. Sect. B 2002, 58, 380-388; 69% possess one-dimensional ladder-like tapes (i), 5% form nonreciprocal hydrogen bonded networks (ii), and 26% develop alternate hydrogen bonded structures involving piperazinedione side chains and/or included small molecules. (Chemical Equation Presented)
    • In October, 2007, 109 nonionic piperazinediones with 3D coordinates were retrieved from the Cambridge Structural Database (CSD, version 5.27 plus three updates; see (a) Allen, F. H. Acta Crystallogr. Sect. B 2002, 58, 380-388; 69% possess one-dimensional "ladder-like" tapes (i), 5% form nonreciprocal hydrogen bonded networks (ii), and 26% develop alternate hydrogen bonded structures involving piperazinedione side chains and/or included small molecules. (Chemical Equation Presented)
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    • and references cited therein. Organic zeolites are exceptions; see a
    • Organic zeolites are exceptions; see (a) Feldman, K. S.; Liu, Y.; Saunders, J. C.; Masters, K. M.; Campbell, R. F. Heterocycles 2001, 55, 1527-1554, and references cited therein.
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    • Feldman, K.S.1    Liu, Y.2    Saunders, J.C.3    Masters, K.M.4    Campbell, R.F.5
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    • Other terms that have been used to designate arene interaction motifs include, for parallel center-to-center (iii), face-to-face, face-to-face stacked, parallel stacked, and stacked; for parallel edge-to-center (iv) face-to-face center-to-edge, parallel offset, offset stacked, and offset nonstacked; and for perpendicular edge-to-center (v) edge-to-face, edge-face, herringbone, and T-type. (Figure Presented)
    • Other terms that have been used to designate arene interaction motifs include, for parallel center-to-center (iii), face-to-face, face-to-face stacked, parallel stacked, and stacked; for parallel edge-to-center (iv) face-to-face center-to-edge, parallel offset, offset stacked, and offset nonstacked; and for perpendicular edge-to-center (v) edge-to-face, edge-face, herringbone, and T-type. (Figure Presented)
  • 42
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    • Ref 1 pp 12-14 and 31-33; ref 2 p 13; ref 19 pp 144-154
    • Ref 1 pp 12-14 and 31-33; ref 2 p 13; ref 19 pp 144-154.
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    • Purchased from Aldrich Chemical Company
    • Purchased from Aldrich Chemical Company.
  • 54
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    • Dipole moments listed in Table 2 were calculated from the crystal structure coordinates at the semi-empirical AM1 level (single point energy) using Spartan '02 v1.0.4e.
    • Dipole moments listed in Table 2 were calculated from the crystal structure coordinates at the semi-empirical AM1 level (single point energy) using Spartan '02 v1.0.4e.
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  • 60
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    • Dipole moments of model compounds vi-viii were calculated at the semiempirical AM1 level (equilibrium geometry) using Spartan '02 v1.0.4e.
    • Dipole moments of model compounds vi-viii were calculated at the semiempirical AM1 level (equilibrium geometry) using Spartan '02 v1.0.4e.
  • 61
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    • Chemical Equation Presented, 61 Conformational energies (A values) indicate the nitro group (4.8 kJ/ mol) is larger than nitrile (0.48 kJ/mol, bromine (ca. 2.4 kJ/mol, or methoxy (ca. 2.7 kJ/mol) groups. See (a) Eliel, E. L, Wilen, S. H, Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994, p 696 and references cited therein. increments for these groups are CN, 16 Å3; Br, 26 Å3; NO2, 23 Å3; and OMe, ca. 30 Å3. See ref 21 page 20
    • 3. See ref 21 page 20.


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