The halogen-bonded adduct 1,4-bis(pyri-din-4-yl)buta-1,3-diyne-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexa-deca-fluoro-1,8-diiodo-octane (1/1).

In the crystal structure of the title compound, C8F16I2·C14H8N2, the mol-ecules form infinite chains parallel to [2-11] through two symmetry-independent C-I⋯N halogen bonds (XBs). As commonly found, the perfluoro-alkyl mol-ecules segregate from the hydro-carbon ones, forming a layered structure. Apart from the XBs, the only contact below the sum of van der Waals radii is a weak H⋯F contact. The topology of the network is a nice example of the paradigm of the expansion of ditopic starting modules; the XB leads to the construction of infinite supramolecular chains along [2-11] formed by alternating XB donors and acceptors.

Related literature

For the use of bis-(4-pyrid­yl)buta-1,3-diine in crystal engeneering based on hydrogen bonding and transition metal binding, see: Nakamura et al. (2003 ▶); Curtis et al. (2005 ▶); Maekawa et al. (2000 ▶); Badruz Zaman et al. (2001 ▶); Allan et al. (1988 ▶). For N⋯I halogen bonds based on α,ω-diiodo­per­fluoro­carbons, see: Neukirch et al. (2005 ▶); Navarrini et al. (2000 ▶); Liantonio et al. (2003 ▶); Bertani et al. (2002 ▶); Metrangolo et al. (2004 ▶, 2008 ▶); Fox et al. (2004 ▶); Dey et al. (2009 ▶). For segregation of perfluoro­alkyl chains, see: Fox et al. (2008 ▶). For chirality and order/disorder of long perfluoro­alkyl chains, see: Monde et al. (2006 ▶). For the synthesis of bis-(4-pyrid­yl)buta-1,3-diine, see: Della Ciana & Haim (1984 ▶).

Experimental

Crystal data

C8F16I2·C14H8N2

M = 858.10

Triclinic,

a = 5.4849 (11) Å

b = 14.302 (2) Å

c = 18.354 (3) Å

α = 111.40 (2)°

β = 90.35 (2)°

γ = 94.03 (2)°

V = 1336.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 2.48 mm−1

T = 295 K

0.36 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.734, T max = 1.000

15067 measured reflections

6100 independent reflections

4600 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.02

6100 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001888/fy2080sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001888/fy2080Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001888/fy2080Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8F16I2·C14H8N2	Z = 2
Mr = 858.10	F(000) = 808
Triclinic, P1	Dx = 2.132 Mg m−3
a = 5.4849 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.302 (2) Å	Cell parameters from 981 reflections
c = 18.354 (3) Å	θ = 2.4–27.4°
α = 111.40 (2)°	µ = 2.48 mm−1
β = 90.35 (2)°	T = 295 K
γ = 94.03 (2)°	Elongated prism, colourless
V = 1336.4 (4) Å3	0.36 × 0.12 × 0.10 mm

Bruker SMART CCD area detector diffractometer	4600 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 27.5°, θmin = 2.3°
Tmin = 0.734, Tmax = 1.000	h = −7→7
15067 measured reflections	k = −18→18
6100 independent reflections	l = −23→23

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.5679P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
6100 reflections	Δρmax = 0.90 e Å−3
379 parameters	Δρmin = −0.57 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
I1	0.11335 (6)	0.46492 (2)	0.32421 (2)	0.06421 (11)
C1	−0.0850 (8)	0.5404 (4)	0.2631 (3)	0.0616 (10)
F1	−0.1957 (7)	0.6162 (3)	0.3136 (2)	0.1019 (12)
F2	−0.2603 (6)	0.4751 (3)	0.2165 (2)	0.0938 (10)
C2	0.0789 (7)	0.5809 (3)	0.2117 (2)	0.0525 (9)
F3	0.2403 (6)	0.6512 (3)	0.25989 (19)	0.0936 (10)
F4	0.1996 (6)	0.5068 (2)	0.16550 (18)	0.0852 (9)
C3	−0.0565 (8)	0.6289 (3)	0.1613 (2)	0.0598 (10)
F5	−0.1913 (8)	0.6966 (3)	0.2048 (2)	0.1254 (16)
F6	−0.2101 (6)	0.5560 (3)	0.1115 (2)	0.1027 (12)
C4	0.1092 (8)	0.6720 (3)	0.1114 (2)	0.0558 (9)
F7	0.2517 (11)	0.7470 (4)	0.1598 (3)	0.170 (3)
F8	0.2464 (7)	0.6031 (4)	0.0697 (3)	0.1272 (17)
C5	−0.0268 (8)	0.7128 (3)	0.0561 (2)	0.0569 (10)
F9	−0.1635 (10)	0.7821 (4)	0.0985 (2)	0.152 (2)
F10	−0.1735 (7)	0.6388 (3)	0.0088 (2)	0.1142 (14)
C6	0.1400 (8)	0.7555 (3)	0.0062 (2)	0.0546 (9)
F11	0.2902 (7)	0.8298 (3)	0.0525 (2)	0.1111 (13)
F12	0.2741 (6)	0.6821 (3)	−0.0373 (2)	0.0963 (11)
C7	0.0006 (7)	0.7947 (3)	−0.0502 (2)	0.0519 (9)
F13	−0.1322 (6)	0.8675 (2)	−0.00739 (17)	0.0850 (9)
F14	−0.1497 (6)	0.7197 (2)	−0.09729 (17)	0.0826 (9)
C8	0.1623 (9)	0.8356 (4)	−0.1016 (3)	0.0651 (11)
F15	0.3155 (6)	0.9102 (3)	−0.0564 (2)	0.1065 (12)
F16	0.2988 (7)	0.7622 (3)	−0.1455 (2)	0.1068 (13)
I2	−0.04797 (6)	0.88682 (2)	−0.17707 (2)	0.06339 (11)
C9	0.4885 (9)	0.3202 (4)	0.5119 (3)	0.0669 (12)
H1B	0.4645	0.3284	0.5639	0.080*
C10	0.3452 (9)	0.3656 (4)	0.4747 (3)	0.0758 (13)
H10	0.2236	0.4041	0.5031	0.091*
N1	0.3700 (8)	0.3578 (3)	0.4013 (3)	0.0730 (11)
C11	0.5425 (10)	0.3021 (5)	0.3621 (3)	0.0775 (14)
H11	0.5607	0.2952	0.3101	0.093*
C12	0.6971 (9)	0.2536 (4)	0.3932 (3)	0.0689 (12)
H12	0.8175	0.2160	0.3634	0.083*
C13	0.6682 (7)	0.2623 (3)	0.4706 (2)	0.0553 (9)
C14	0.8229 (8)	0.2136 (4)	0.5068 (3)	0.0616 (10)
C15	0.9543 (9)	0.1761 (4)	0.5378 (3)	0.0651 (11)
C16	1.1066 (9)	0.1343 (4)	0.5753 (3)	0.0646 (11)
C17	1.2428 (9)	0.0982 (4)	0.6076 (3)	0.0654 (11)
C18	1.3964 (8)	0.0545 (3)	0.6481 (2)	0.0565 (10)
C19	1.3530 (9)	0.0648 (4)	0.7250 (3)	0.0678 (11)
H19	1.2238	0.0998	0.7514	0.081*
C20	1.5051 (9)	0.0220 (4)	0.7606 (3)	0.0674 (11)
H20	1.4754	0.0291	0.8121	0.081*
N2	1.6933 (7)	−0.0291 (3)	0.7268 (2)	0.0699 (10)
C21	1.7289 (9)	−0.0398 (4)	0.6527 (3)	0.0743 (13)
H21	1.8567	−0.0769	0.6274	0.089*
C22	1.5882 (9)	0.0006 (4)	0.6113 (3)	0.0706 (13)
H22	1.6214	−0.0082	0.5597	0.085*

	U11	U22	U33	U12	U13	U23
I1	0.06808 (19)	0.0752 (2)	0.06554 (19)	0.00504 (14)	−0.00501 (13)	0.04518 (15)
C1	0.065 (3)	0.071 (3)	0.062 (2)	0.017 (2)	0.009 (2)	0.037 (2)
F1	0.132 (3)	0.111 (2)	0.094 (2)	0.070 (2)	0.056 (2)	0.0628 (19)
F2	0.0727 (18)	0.119 (3)	0.116 (3)	−0.0210 (18)	−0.0270 (17)	0.079 (2)
C2	0.054 (2)	0.057 (2)	0.052 (2)	0.0110 (18)	0.0002 (17)	0.0243 (18)
F3	0.108 (2)	0.100 (2)	0.084 (2)	−0.0334 (19)	−0.0355 (18)	0.0554 (18)
F4	0.103 (2)	0.101 (2)	0.0805 (18)	0.0584 (18)	0.0315 (16)	0.0569 (16)
C3	0.068 (3)	0.067 (2)	0.056 (2)	0.021 (2)	0.006 (2)	0.034 (2)
F5	0.171 (4)	0.146 (3)	0.112 (3)	0.114 (3)	0.073 (3)	0.091 (2)
F6	0.091 (2)	0.135 (3)	0.110 (3)	−0.040 (2)	−0.0437 (19)	0.087 (2)
C4	0.061 (2)	0.058 (2)	0.060 (2)	0.0006 (19)	−0.0104 (18)	0.0354 (19)
F7	0.238 (5)	0.165 (4)	0.139 (3)	−0.132 (4)	−0.127 (4)	0.120 (3)
F8	0.122 (3)	0.180 (4)	0.158 (3)	0.098 (3)	0.080 (3)	0.138 (3)
C5	0.067 (2)	0.060 (2)	0.049 (2)	0.021 (2)	0.0048 (18)	0.0245 (18)
F9	0.222 (5)	0.187 (4)	0.122 (3)	0.158 (4)	0.109 (3)	0.118 (3)
F10	0.107 (3)	0.161 (3)	0.101 (2)	−0.058 (2)	−0.046 (2)	0.092 (3)
C6	0.061 (2)	0.057 (2)	0.053 (2)	0.0073 (18)	−0.0054 (18)	0.0279 (18)
F11	0.130 (3)	0.118 (3)	0.105 (2)	−0.055 (2)	−0.068 (2)	0.077 (2)
F12	0.101 (2)	0.128 (3)	0.102 (2)	0.069 (2)	0.0459 (18)	0.081 (2)
C7	0.057 (2)	0.054 (2)	0.050 (2)	0.0100 (17)	−0.0028 (17)	0.0253 (17)
F13	0.105 (2)	0.098 (2)	0.0755 (17)	0.0553 (18)	0.0257 (16)	0.0516 (16)
F14	0.095 (2)	0.0869 (19)	0.0769 (18)	−0.0257 (16)	−0.0342 (16)	0.0497 (15)
C8	0.062 (3)	0.079 (3)	0.070 (3)	0.009 (2)	−0.001 (2)	0.045 (2)
F15	0.093 (2)	0.131 (3)	0.123 (3)	−0.044 (2)	−0.047 (2)	0.089 (2)
F16	0.110 (2)	0.147 (3)	0.109 (2)	0.073 (2)	0.051 (2)	0.090 (2)
I2	0.07009 (19)	0.0747 (2)	0.06057 (18)	0.00691 (14)	−0.00418 (13)	0.04264 (15)
C9	0.061 (2)	0.090 (3)	0.062 (3)	0.006 (2)	0.000 (2)	0.042 (2)
C10	0.066 (3)	0.093 (3)	0.088 (3)	0.026 (3)	0.008 (2)	0.052 (3)
N1	0.064 (2)	0.091 (3)	0.086 (3)	0.011 (2)	−0.005 (2)	0.058 (2)
C11	0.078 (3)	0.110 (4)	0.066 (3)	0.006 (3)	−0.002 (2)	0.057 (3)
C12	0.068 (3)	0.087 (3)	0.063 (3)	0.017 (2)	0.004 (2)	0.038 (2)
C13	0.050 (2)	0.064 (2)	0.060 (2)	0.0001 (18)	−0.0102 (17)	0.034 (2)
C14	0.062 (2)	0.073 (3)	0.062 (2)	0.003 (2)	−0.0062 (19)	0.039 (2)
C15	0.067 (3)	0.069 (3)	0.070 (3)	0.010 (2)	−0.009 (2)	0.038 (2)
C16	0.067 (3)	0.071 (3)	0.067 (3)	0.008 (2)	−0.006 (2)	0.038 (2)
C17	0.066 (3)	0.071 (3)	0.069 (3)	0.010 (2)	−0.008 (2)	0.038 (2)
C18	0.061 (2)	0.057 (2)	0.062 (2)	0.0009 (18)	−0.0117 (19)	0.0348 (19)
C19	0.070 (3)	0.076 (3)	0.057 (2)	0.012 (2)	−0.007 (2)	0.023 (2)
C20	0.075 (3)	0.080 (3)	0.055 (2)	0.002 (2)	−0.010 (2)	0.036 (2)
N2	0.064 (2)	0.086 (3)	0.077 (3)	−0.001 (2)	−0.0163 (19)	0.051 (2)
C21	0.066 (3)	0.091 (3)	0.081 (3)	0.020 (3)	−0.002 (2)	0.047 (3)
C22	0.064 (3)	0.104 (4)	0.062 (3)	0.016 (3)	0.000 (2)	0.051 (3)

I1—C1	2.154 (4)	C9—C10	1.376 (6)
C1—F1	1.330 (5)	C9—C13	1.377 (7)
C1—F2	1.345 (6)	C9—H1B	0.9300
C1—C2	1.540 (6)	C10—N1	1.320 (7)
C2—F4	1.316 (5)	C10—H10	0.9300
C2—F3	1.338 (5)	N1—C11	1.321 (7)
C2—C3	1.552 (5)	C11—C12	1.376 (7)
C3—F5	1.290 (5)	C11—H11	0.9300
C3—F6	1.344 (6)	C12—C13	1.390 (6)
C3—C4	1.545 (6)	C12—H12	0.9300
C4—F8	1.298 (6)	C13—C14	1.436 (6)
C4—F7	1.315 (5)	C14—C15	1.185 (6)
C4—C5	1.552 (6)	C15—C16	1.375 (6)
C5—F9	1.303 (5)	C16—C17	1.204 (6)
C5—F10	1.312 (6)	C17—C18	1.434 (6)
C5—C6	1.546 (6)	C18—C22	1.378 (7)
C6—F11	1.319 (5)	C18—C19	1.389 (6)
C6—F12	1.336 (5)	C19—C20	1.362 (6)
C6—C7	1.563 (5)	C19—H19	0.9300
C7—F13	1.322 (5)	C20—N2	1.330 (7)
C7—F14	1.330 (5)	C20—H20	0.9300
C7—C8	1.536 (6)	N2—C21	1.329 (6)
C8—F15	1.324 (6)	C21—C22	1.372 (6)
C8—F16	1.346 (6)	C21—H21	0.9300
C8—I2	2.151 (4)	C22—H22	0.9300
F1—C1—F2	107.3 (4)	F15—C8—F16	107.0 (4)
F1—C1—C2	109.0 (4)	F15—C8—C7	109.4 (4)
F2—C1—C2	108.1 (4)	F16—C8—C7	108.8 (4)
F1—C1—I1	110.5 (3)	F15—C8—I2	109.8 (3)
F2—C1—I1	108.9 (3)	F16—C8—I2	109.3 (3)
C2—C1—I1	112.9 (3)	C7—C8—I2	112.5 (3)
F4—C2—F3	108.4 (4)	C10—C9—C13	118.7 (4)
F4—C2—C1	108.5 (3)	C10—C9—H1B	120.6
F3—C2—C1	107.0 (3)	C13—C9—H1B	120.6
F4—C2—C3	109.1 (3)	N1—C10—C9	123.9 (5)
F3—C2—C3	108.2 (3)	N1—C10—H10	118.1
C1—C2—C3	115.4 (3)	C9—C10—H10	118.1
F5—C3—F6	106.3 (4)	C10—N1—C11	117.0 (4)
F5—C3—C4	110.6 (4)	N1—C11—C12	124.2 (5)
F6—C3—C4	107.1 (3)	N1—C11—H11	117.9
F5—C3—C2	110.1 (4)	C12—C11—H11	117.9
F6—C3—C2	107.0 (4)	C11—C12—C13	118.1 (5)
C4—C3—C2	115.2 (3)	C11—C12—H12	120.9
F8—C4—F7	108.2 (5)	C13—C12—H12	120.9
F8—C4—C3	109.2 (3)	C9—C13—C12	118.1 (4)
F7—C4—C3	107.6 (4)	C9—C13—C14	120.8 (4)
F8—C4—C5	108.6 (4)	C12—C13—C14	121.1 (4)
F7—C4—C5	107.7 (4)	C15—C14—C13	178.1 (5)
C3—C4—C5	115.4 (4)	C14—C15—C16	178.8 (6)
F9—C5—F10	107.2 (5)	C17—C16—C15	179.1 (6)
F9—C5—C6	109.6 (4)	C16—C17—C18	177.5 (5)
F10—C5—C6	108.5 (3)	C22—C18—C19	118.6 (4)
F9—C5—C4	108.2 (4)	C22—C18—C17	120.8 (4)
F10—C5—C4	107.9 (4)	C19—C18—C17	120.6 (4)
C6—C5—C4	115.2 (4)	C20—C19—C18	118.1 (5)
F11—C6—F12	108.1 (4)	C20—C19—H19	121.0
F11—C6—C5	109.6 (4)	C18—C19—H19	121.0
F12—C6—C5	107.9 (3)	N2—C20—C19	124.4 (4)
F11—C6—C7	108.4 (3)	N2—C20—H20	117.8
F12—C6—C7	108.0 (3)	C19—C20—H20	117.8
C5—C6—C7	114.7 (3)	C21—N2—C20	116.6 (4)
F13—C7—F14	108.4 (4)	N2—C21—C22	123.8 (5)
F13—C7—C8	108.1 (3)	N2—C21—H21	118.1
F14—C7—C8	107.8 (3)	C22—C21—H21	118.1
F13—C7—C6	108.2 (3)	C21—C22—C18	118.4 (4)
F14—C7—C6	108.5 (3)	C21—C22—H22	120.8
C8—C7—C6	115.6 (3)	C18—C22—H22	120.8
F1—C1—C2—F4	176.0 (4)	F10—C5—C6—F12	−62.3 (5)
F2—C1—C2—F4	−67.7 (4)	C4—C5—C6—F12	58.8 (5)
I1—C1—C2—F4	52.8 (4)	F9—C5—C6—C7	−58.7 (5)
F1—C1—C2—F3	59.2 (5)	F10—C5—C6—C7	58.1 (5)
F2—C1—C2—F3	175.5 (4)	C4—C5—C6—C7	179.1 (3)
I1—C1—C2—F3	−64.0 (4)	F11—C6—C7—F13	−63.1 (5)
F1—C1—C2—C3	−61.3 (5)	F12—C6—C7—F13	−179.9 (4)
F2—C1—C2—C3	55.0 (5)	C5—C6—C7—F13	59.8 (5)
I1—C1—C2—C3	175.5 (3)	F11—C6—C7—F14	179.6 (4)
F4—C2—C3—F5	175.0 (4)	F12—C6—C7—F14	62.7 (5)
F3—C2—C3—F5	−67.2 (5)	C5—C6—C7—F14	−57.6 (5)
C1—C2—C3—F5	52.6 (6)	F11—C6—C7—C8	58.3 (5)
F4—C2—C3—F6	59.9 (5)	F12—C6—C7—C8	−58.5 (5)
F3—C2—C3—F6	177.6 (4)	C5—C6—C7—C8	−178.8 (4)
C1—C2—C3—F6	−62.6 (5)	F13—C7—C8—F15	63.4 (5)
F4—C2—C3—C4	−59.1 (5)	F14—C7—C8—F15	−179.7 (4)
F3—C2—C3—C4	58.7 (5)	C6—C7—C8—F15	−58.0 (5)
C1—C2—C3—C4	178.5 (4)	F13—C7—C8—F16	180.0 (4)
F5—C3—C4—F8	178.5 (4)	F14—C7—C8—F16	−63.1 (4)
F6—C3—C4—F8	−66.0 (5)	C6—C7—C8—F16	58.5 (5)
C2—C3—C4—F8	52.9 (5)	F13—C7—C8—I2	−58.8 (4)
F5—C3—C4—F7	61.3 (6)	F14—C7—C8—I2	58.1 (4)
F6—C3—C4—F7	176.8 (4)	C6—C7—C8—I2	179.7 (3)
C2—C3—C4—F7	−64.3 (5)	C13—C9—C10—N1	−0.5 (8)
F5—C3—C4—C5	−58.9 (5)	C9—C10—N1—C11	0.6 (8)
F6—C3—C4—C5	56.6 (5)	C10—N1—C11—C12	−0.8 (8)
C2—C3—C4—C5	175.5 (4)	N1—C11—C12—C13	1.0 (9)
F8—C4—C5—F9	−179.8 (4)	C10—C9—C13—C12	0.6 (7)
F7—C4—C5—F9	−62.9 (6)	C10—C9—C13—C14	179.8 (5)
C3—C4—C5—F9	57.2 (6)	C11—C12—C13—C9	−0.8 (7)
F8—C4—C5—F10	64.5 (5)	C11—C12—C13—C14	179.9 (5)
F7—C4—C5—F10	−178.6 (4)	C22—C18—C19—C20	0.9 (7)
C3—C4—C5—F10	−58.5 (5)	C17—C18—C19—C20	−179.8 (5)
F8—C4—C5—C6	−56.9 (5)	C18—C19—C20—N2	0.0 (8)
F7—C4—C5—C6	60.1 (6)	C19—C20—N2—C21	−1.3 (8)
C3—C4—C5—C6	−179.8 (3)	C20—N2—C21—C22	1.7 (8)
F9—C5—C6—F11	63.5 (5)	N2—C21—C22—C18	−0.8 (9)
F10—C5—C6—F11	−179.7 (4)	C19—C18—C22—C21	−0.5 (7)
C4—C5—C6—F11	−58.7 (5)	C17—C18—C22—C21	−179.8 (5)
F9—C5—C6—F12	−179.0 (4)

C—X···Y	X···Y	C—X···Y
C1—I1···N1	2.863 (4)	177.93 (16)
C8—I2···N2i	2.887 (4)	175.39 (16)
C1—F1···H9ii	2.60	145.3

Molecule A	Molecul B	A site	B site
C14H8N2a	I-(CF2)8-I	C1	C1
C10H16N2b	I-(CF2)8-Ic	C1	C1
C12H26N2O2d	I-(CF2)8-I	Ci	C2
C10H16N2e	Br-(CF2)8-Br	C2	Ci
C13H14N2f	I-(CF2)8-I	Ci	Ci
CN-(CH2)4-CNg	I-(CF2)2-I	Ci	Ci
CN-(CH2)4-CNg	I-(CF2)4-I	Ci	Ci
CN-(CH2)6-CNg	I-(CF2)4-I	Ci	Ci
CN-(CH2)4-CNg	I-(CF2)6-I	Ci	Ci
CN-(CH2)6-CNg	I-(CF2)6-I	Ci	Ci
CN-(CH2)4-CNg	I-(CF2)8-I	Ci	Ci
CN-(CH2)6-CNg	I-(CF2)8-I	Ci	Ci
C10H8N4h	I-(CF2)8-I	C1	Ci
C10H8N4i	I-(CF2)4-I	C1	Ci

Table 1

Halogen and hydrogen-bonding contacts (Å, °)

C—X⋯Y	X⋯Y	C—X⋯Y
C1—I1⋯N1	2.863 (4)	177.93 (16)
C8—I2⋯N2i	2.887 (4)	175.39 (16)
C1—F1⋯H9ii	2.60	145.3

Symmetry codes: (i) = −2 + x, 1 + y, −1 + z; (ii) = −x, 1 − y, 1 − z.