Table 4.

Relevant covalent bond, hydrogen bond and halogen bond lengths and angles in 9–12.

	C–X [Å] [X]	X···Cl− [Å] [Cl−] [R]*	C–X···Cl−	Cl−···H–N [Å]	N–H···Cl−
3-IPyBnCl, 9	2.101 [I1]	3.151 [Cl1] [0.83]	174.1°	–	–
	2.099 [I15]	3.223 [Cl2] [0.85]	174.6°	–	–
3-IPyHCl, 10	2.096 [I1]	3.189 [Cl1] [0.84]	174.3°	3.035	163.0°
	2.114 [I8]	3.170 [Cl4] [0.84]	179.7°	3.058	146.0°
	2.105 [I15]	3.141 [Cl1] [0.83]	177.3°	3.044	149.4°
	2.096 [I22]	3.227 [Cl4] [0.85]	173.8°	3.024	164.9°
3-BrPyHCl, 11 (CIHBAX [41])	1.890 [Br1]	3.359 [Cl1] [0.89]	162.2°	2.995	152.9°
3-ClPyHCl, 12 (VOQMUJ [42])	1.727 [Cl1]	3.479 [Cl2] [0.92]	156.1°	2.993	169.4°

^* R = d/(r_X + r_D), see Equation 1.