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Table 3 Hydrogen bond metrics for compounds 1a-7b

From: Design of co-crystals/salts of some Nitrogenous bases and some derivatives of thiophene carboxylic acids through a combination of hydrogen and halogen bonds

D---H....A H…A (Ǻ) D…A (Ǻ) D -H…A Symmetry operation
5TPC AMPY (1a)     
O1A-H1A∙∙∙N1B 1.66(4) 2.636(4) 172(3)  
O3A-H3A∙∙∙N3B 1.70(4) 2.682(3) 178(4)  
N4B-H3C∙∙∙O2A 2.08 2.928(4) 170  
N4B-H3D∙∙∙O4A 2.05 2.902(4) 171  
C8A-H8A∙∙∙O4A 2.55 3.419(5) 155 1-x,-y,1-z
C8B-H8E∙∙∙O4A 2.60 3.495(5) 156 1-x,1-y,1-z
C-X…Cg X…Cg (Å) C-X..Cg (°) Y..Cg (Å) Symmetry code
C5A-Cl1A Cg3 3.7555(19) 92.33(12) 4.190(4) -1 + X,1/2-Y,-1/2 + Z
C10A-Cl2A Cg2 3.9862(19) 88.75(14) 4.302(4) 1 + X,1/2-Y,1/2 + Z
TPCAMPY(2a)     
N1B-H1B∙∙∙O2A 1.74 2.593(4) 171  
N4B-H4C∙∙∙N3B 2.19 3.043(5) 171 -x,1-y,2-z
N4B-H4D∙∙∙O1A 2.08 2.912(4) 164  
C5A-H5A∙∙∙O1A 2.51 3.417(4) 165 x,1/2-y,-1/2 + z
TDCAMPY(3a)     
N4C-H4E∙∙∙O2A 2.07 2.926(3) 173 1-x,-1/2 + y,3/2-z
N4C-H4F∙∙∙O4A 2.00 2.853(3) 171  
N4D-H4H∙∙∙O2B 2.04 2.897(3) 174  
N4D-H4I∙∙∙O4B 2.08 2.933(3) 171 2-x,-1/2 + y,1/2-z
O1A-H11A∙∙∙N3C 1.83(3) 2.608(3) 166(3) 1-x,1/2 + y,3/2-z
O1B-H11B∙∙∙N1D 1.96(3) 2.660(3) 171(3)  
O3A-H33A∙∙∙N1C 1.67(3) 2.643(3) 177(3)  
O3B-H33B∙∙∙N3D 1.69(3) 2.636(3) 167(3) 2-x,1/2 + y,1/2-z
5TPC CYT(4a)     
N1A-H1A∙∙∙O2 1.96 2.759(3) 154 1-x,2-y,1-z
N1B-H1B∙∙∙O1 1.76 2.6194(18) 172  
N3B-H3B∙∙∙N3A 2.00 2.8586(17) 177  
N4A-H4C∙∙∙O3B 2.06 2.9234(19) 176  
N4A-H4D∙∙∙O3A 2.15 2.8632(19) 140 x,-1 + y,z
N4B-H4E∙∙∙O3A 1.92 2.7836(19) 177  
N4B-H4F∙∙∙O3B 2.09 2.8626(18) 149 x,1 + y,z
C-X…Cg X…Cg (Å) C-X..Cg (°) Y..Cg (Å) Symmetry code
C5-Cl1 Cg3 3.6501(10) 97.03(7) 4.220(2) -X,1-Y,-Z
C1-O1 Cg2 3.4019(16) 141.27(12 4.460(2) -X,2-Y,1-Z
C2A-O3A Cg1 3.4771(14) 69.46(9) 3.2563(16) 1-X,2-Y,1-Z
5TPC BA(5a)     
N1 –H1∙∙∙O1 2.00(6) 2.886(7) 169(7) -1 + x,y,z
O2 -H2A∙∙∙N5 1.85(6) 2.631(6) 173(8) 1 + x,y,z
N4 –H4 ∙∙∙N3 1.89(6) 2.886(7) 169(6) 1-x,-y,1-z
C8 –H8 ∙∙∙N1 2.54 2.875(8) 101  
C11-H11∙∙∙O2 2.60 3.479(9) 158 x,1 + y,z
C-X…Cg X…Cg (Å) C-X..Cg (°) Y..Cg (Å) Symmetry code
C5A-Cl1A Cg3 3.874(3) 127.9(3) 5.105(7) -1-X,1-Y,2-Z
C1A-O2A Cg1 3.945(5) 63.4(3) 3.571(6) -1 + X,Y,Z
C1A-O2A Cg5 3.962(5) 69.1(3) 3.707(6) 1 + X,Y,Z
5TPC2NPY(6a)     
N1B-H1B∙∙∙O1A 1.82 2.6667(17) 169  
N2B-H2C∙∙∙O2A 1.94 2.7861(19) 169  
N2B-H2D∙∙∙O1A 2.03 2.8873(19) 172 x,3/2-y,1/2 + z
C2B-H2B∙∙∙O2A 2.48 3.211(2) 135 1-x,1/2 + y,3/2-z
C-X…Cg X…Cg (Å) C-X..Cg (°) Y..Cg (Å) Symmetry code
C3B-H3B Cg2 2.93 133 3.628(2) 1 + X,3/2-Y,1/2 + Z
5TPC ACR(7a)     
O1A-H1A∙∙∙N1B 1.721(19) 2.574(2) 168(2)