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Figure 6
Scatter plots of the intermolecular N⋯X distance d (Å) versus the C—X⋯N (ANG1) and C—N⋯X (ANG2) angles (°) for (a) C—F⋯N≡C, (b) C—Cl⋯N≡C, (c) C—Br⋯N≡C and (d) C—I⋯N≡C contacts retrieved from the CSD (Version 5.36, November 2014). The positions of the C—X⋯N≡C interactions observed in the crystal structures of compounds (3)[link] and (4)[link] are marked (×) in parts (b) and (c), respectively. The average values of the interaction distances and angles (standard uncertainties are given in parentheses) for individual cyano–halogen contacts are: N⋯F = 2.97 Å (0.03), C—F⋯N = 122.28° (23.52) and C—N⋯F = 116.43° (16.59); N⋯Cl = 3.18 Å (0.08), C—Cl⋯N = 159.93° (12.60) and C—N⋯Cl = 127.33° (16.95); N⋯Br = 3.19 Å (0.09), C—Br⋯N = 165.90° (6.23) and C—N⋯Br = 130.05° (19.33); N⋯I = 3.14 (0.13), C—I⋯N = 169.99° (7.48) and C—N⋯I = 147.17° (19.38). Entries with disorder on either of the interacting atoms were excluded from the plot and in the calculation of average values.

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 71| Part 10| October 2015| Pages 921-928
doi:10.1107/S2053229615017106
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