Table 1. Halogen Bond Lengths (d), Angles (∠), and Relative Shortenings (R.S.) of D···A Distances in the Herein Prepared Cocrystals.

cocrystal	D···A	acceptor moiety	d(D···A)/Å	R.S.a/%	∠(C–D···A)/°
(BM)2(14tfib)5	I1···O1	carbonyl	2.879	17.7	177.3
	I2···O2	morpholine	2.950	15.7	179.8
	I3···N2	morpholine	3.035	14.0	169.7
(BM)(135tfib)2	I1···O1	carbonyl	2.997	14.4	175.3
	I4···N2	morpholine	3.008	14.8	165.9
	I5···O2	morpholine	3.243	7.3	143.3
(BP)(14tfib)	I2···N2	proximal piperazine	2.948	16.5	176.5
	I1···N3	terminal piperazine	2.760	21.8	177.3
(BP)(135tfib)2	I10···O1	carbonyl	2.917	16.7	173.6
	I7···N2	proximal piperazine	2.984	15.5	171.6
	I4···N3	terminal piperazine	2.948	16.5	171.1
	I2···O2	carbonyl	2.931	16.3	171.5
	I5···N5	proximal piperazine	2.961	16.1	173.5
	I8···N6	terminal piperazine	2.953	16.4	167.0
(AM)(14tfib)	I1···O1	carbonyl	2.800	20.0	174.1
	I2···O2	morpholine	3.015	13.9	177.5
(AM)(135tfib)2	I2···O1	carbonyl	2.972	15.1	173.1
	I4···O2	morpholine	3.062	12.5	168.6
	I5···N2	morpholine	3.119	11.6	173.4
	I10···O3	carbonyl	2.846	18.7	174.8
	I9···O4	morpholine	2.979	14.9	165.7
	I7···N4	morpholine	2.981	15.6	173.6
(AP)(14tfib)	I1···N3	terminal piperazine	2.721	22.9	176.8
	I2···O1	carbonyl	2.810	19.7	178.8
(AP)(135tfib)	I1···N3	terminal piperazine	2.779	21.3	176.4
	I3···O1	carbonyl	2.846	18.7	178.2
	I1···I2	135tfib	3.959	0.03	163.5

^aR.S. = 1 – d(D···A)/[r_vdW(D) + r_vdW(A)].⁷¹