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. 2019 Jun 4;14(6):e0217270. doi: 10.1371/journal.pone.0217270

Table 4. List of intra- and intermolecular interactions present in compounds 5c and 5d.

Motifs D–H…A Symmetry Geometry
D…A/Å H…A/ Å ∠D–H…A/°
5c [C1 > C23 –first molecule; C24 > C46 –second molecule]
I C2-H2···O3 x, y, z (intra) 3.028(2) 2.45 112
C5-H5···O2 2.862(2) 2.21 117
C16···O4 2.724(2) - -
C16···C11(π) 3.073(2) - -
C24-H24···O8 2.868(2) 2.21 117
C27-H27···O9 3.007(2) 2.41 113
C42···O10 2.793(2) - -
C42···C34(π) 3.026(2)
II C11-H11···O12 x, y, z 3.739(3) 2.66 175
C12-H12···O9 3.528(3) 2.71 132
C23-H23C···N4 3.761(3) 2.71 164
C17-H17A···N3 3.565(3) 2.77 137
C34-H34···O6 3.535(3) 2.51 157
C44-H44C···N1 3.672(3) 2.61 168
C35-H35···C2(π) 3.927(3) 2.87 168
C12-H12···C27(π) 4.008(3) 2.96 164
III C25-H25···O2 -x+1/2, y-1/2, -z+1/2 3.393(2) 2.31 178
C14-H14···O8 3.212(2) 2.61 115
C12-H12···C14(π) 3.746(2) 2.70 162
IV C23-H23A···O11 x-1/2, -y+1/2, z-1/2 3.356(2) 2.32 159
C20-H20B···O9 3.265(2) 2.53 161
π ···π (molecular stacking) 3.994(3) - -
V C23-H23B···O5 x-1, y, z 3.530(3) 2.51 157
C43-H43B···N2 3.554(3) 2.76 131
VI C4-H4···O8 -x-1/2, y+1/2, -z+1/2 3.801(2) 2.81 153
C37-H37···O2 3.455(2) 2.45 154
VII C45-H45B···O11 x+1, y, z 3.563(2) 2.56 154
O7···C37(π) 3.003(2) - -
VIII C15-H15···O2 -x, -y+1, -z 3.489(3) 2.48 155
C15-H15···C5(π) 3.728(3) 2.88 135
IX C38-H38···O1 x+1/2, -y+1/2, z+1/2 3.441(2) 2.58 136
X C41-H41C···O10 -x,-y+1,-z+1 3.616(2) 2.61 155
5d
I C1-H1···O2 x, y, z (intra) 2.930(2) 2.30 115
C4-H4···O3 3.066(2) 2.48 113
II C18-H18···F1 x+1, y-1, z 3.618(3) 2.55 172
C12-H12···O3 4.664(3) 2.61 145
III C17-H17A···F1 x, y+1, z 3.295(3) 2.47 133
IV C17-H17B···O4 -x+2, -y+1, -z+1 3.546(2) 2.88 119
C18-H18C···O4 2.492(2) 2.84 119
V C17-H17A···O3 x+1, y, z 3.552(3) 2.70 136
C17-H17B···O4 3.548(3) 2.88 120
VI C14-H14···F1 -x+2, -y, -z+1 3.333(2) 2.43 140
VII C19-H19A···O3 x-1, y, z 3.782(3) 2.80 152
C17-H17A···O3 3.552(3) 2.70 136
π ···π (molecular stacking) 3.632-
4.137(3)
- -
VIII C19-H19B···O1 - x-1, -y+2, -z 3.364(2) 2.43 143
IX C2-H2···O2 -x, -y+1, -z 3.377(2) 2.33 162