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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)