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Synthesis and crystal structure of tetra­kis­(ethyl­ammonium) hepta­iodide(3−) iodide

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aDepartment of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska str. 64/13, 01601 Kyiv, Ukraine, and bDepartment of Physics of Polymers and Polymeric Materials, "Petru Poni", Institute of Macromolecular Chemistry, Iasi, Romania
*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 18 September 2026; accepted 19 October 2026; online 30 October 2026)

The crystal structure of the title salt, 4C2H5NH3+·I73−·I−, comprises disordered ethyl­ammonium cations accompanied by an isolated and disordered I− anions and [I7]3– polyiodide anions. The positional disorder of the ethyl­ammonium cations and isolated I− anions is caused by the crystallographically imposed mirror symmetry. The entire [I7]3– polyanion exhibits point group symmetry 2/m and is composed of two neutral I2 mol­ecules acting as connectors between three I− anions. The hepta­iodide anion has a unique linear conformation and forms a slipped-stack layered arrangement along the c axis. The organic cations are accommodated between the anionic units and are linked to them via N—H⋯I hydrogen bonds, establishing a supra­molecular framework. As a novel polyiodide compound, the reported structure expands the known structural diversity and topologies of complex iodine-based systems.

1. Chemical context

Halogens are characterized by remarkable chemical versatility, particularly their ability to form a wide variety of polyhalide anions. Within this class, iodine-based anions have maintained a prominent position in chemical research. A major structural milestone was achieved in 1933 with the first complete crystallographic determination of a polyiodide, ammonium triiodide, (NH4)I3 (Mooney, 1935View full citation). Up until now, a large number of polyiodide anions have been structurally characterized, establishing an impressive range of anions from I2− to I293–. Their rich chemistry has been thoroughly summarized in several comprehensive reviews (Svensson & Kloo, 2003View full citation; Sonnenberg et al., 2020View full citation). This fascinating structural diversity manifests in structural units ranging from discrete anions to complex one-, two-, and three-periodic extended networks.

The great structural variety stems from the ability of iodine atoms to form chains via halogen bonds, a process further shaped by the surrounding counter-ions. These structural features have been rationalized and utilized in template synthesis, as well as in mol­ecular and crystal engineering, where different cations are used to achieve specific structural topologies. Furthermore, polyiodides attract continuing inter­est due to their diversified properties, which allow for useful applications in a variety of areas, including superconductors, solar cells, and optical devices (Küpper et al., 2011View full citation).

In the present article, we report the synthesis and crystal structure analysis of a new polyiodide compound, 4(C2H5NH3)+·I73–·I−.

[Scheme 1]

2. Structural commentary

The title compound crystallizes in the monoclinic space group C2/m, with two ethyl­ammonium cations and five I atoms in the asymmetric unit. In the extended structure, isolated I− and polyiodide [I7]3– anions are present. The positional disorder (Fig. 1[link]) for the two cations is caused by the imposed mirror symmetry and that of the isolated anion (I5) by its special position (2/m; multiplicity 2, Wyckoff letter a).

[Figure 1]
Figure 1
The principal structural units in the crystal structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level; short I—I bonds are drawn as dark solid lines, longer I—I bonds as bright solid lines. [Symmetry codes: (i) 2 − x, y, 1 − z; (ii) 1 − x, 1 − y, 2 − z; (iii) x, 1 − y, z.]

Selected I—I bond lengths and angles of the [I7]3– polyanion are summarized in Table 1[link]. The polyiodide can be described as two neutral I2 mol­ecules (I2, I3) acting as connectors between three I− anions (I1, I4 and its symmetry-related counterpart) in a linear manner. The special position (2 c) of the central I1 atom results in point group symmetry 2/m for the entire polyanion. The I2—I3 distance is slightly longer than that in an elemental iodine mol­ecule (2.72 Å; Svensson & Kloo, 2003View full citation). This is due to the n→σ* character of the halogen bond, which typically elongates the covalent bond of an I2 mol­ecule. The distances between these I2 mol­ecules and the three iodide anions (I1—I2 and I3—I4) are significantly longer. For comparison, similar I—I distances [2.8127 (5), 3.4270 (6) and 3.3875 (7) Å] are observed in [HMTAHD]3+[I7]3– (HMTAHD = 2,2,9,9,16,16-hexa­methyl-2,9,16-triazoniahepta­decane; Lin et al., 2012View full citation). As seen in Table 1[link], the angles between the I atoms in the [I7]3– anion are all close to 180°. This polyiodide species adopts a unique linear conformation that has not been previously reported.

Table 1
Selected structural parameters (Å, °)of the polyiodide anion

I—I bond Length I—I—I Angle
I1—I2 3.4445 (4) I1—I2—I3 177.961 (16)
I2—I3 2.7604 (6) I2—I3—I4 177.540 (16)
I3—I4 3.3747 (5) I2—I1—I2i 180.0
Symmetry code: (i) 2 − x, y, 1 − z.

The negative charge of I− and [I7]3– anions is balanced by four ethyl­ammonium cations. The C—C bond lengths are 1.522 (9) Å and 1.525 (11) Å and the C—N bond lengths are 1.478 (6) and 1.423 (10) Å, which are within the expected ranges for ethyl­ammonium cations (Allen et al., 1987View full citation).

3. Supra­molecular features

The shortest I⋯I distances between the isolated I− and [I7]3– anions are 4.5891 (5) Å [I5A⋯I2i; symmetry code: (i) −Mathematical equation + x, −Mathematical equation + y, z], 4.6691 (3) Å (I5A⋯I1i) and 5.3798 (4) Å (I5A⋯I4), which significantly exceed the sum of the van der Waals radii of 4.3 Å for two iodine atoms (Svensson & Kloo, 2003View full citation), indicating no significant covalent or non-covalent inter­actions between them. The layers of polyiodide anions exhibit a slipped-stack arrangement along the c axis (Fig. 2[link]). The organic cations are located between the anionic chains and are linked to them via N—H⋯I hydrogen bonds (Fig. 3[link], Table 2[link]).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1A⋯I4 0.89 2.77 3.6283 (12) 163
N1—H1B⋯I5A 0.89 2.62 3.481 (4) 163
N1—H1B⋯I5B 0.89 2.64 3.521 (4) 170
N1—H1B⋯I5Bi 0.89 2.70 3.521 (4) 154
N1—H1C⋯I2ii 0.89 3.23 3.794 (4) 123
N1—H1C⋯I4iii 0.89 2.89 3.6283 (12) 141
N2—H2D⋯I4ii 0.89 2.99 3.811 (8) 155
N2—H2E⋯I4iv 0.89 2.76 3.597 (9) 158
N2—H2F⋯I5Bv 0.89 3.03 3.775 (9) 143
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation; (v) Mathematical equation.
[Figure 2]
Figure 2
The crystal structure of the title compound in a view approximately along the b axis.
[Figure 3]
Figure 3
A fragment of crystal structure showing the N—H⋯I hydrogen bonds between ethyl­ammonium cations and both iodide and hepta­iodide anions (N1—C1—C2 cation left; N2–C3—C4 cation right).

4. Database survey

A search in the Cambridge Crystal Database (CSD, version 5.43, last update May 2026; Groom et al., 2016View full citation) for hepta­iodide moieties, including both [I7]− and [I7]3– anions, revealed 33 entries. Among these, only two structures contain an additional, isolated I− anion co-crystallized alongside the hepta­iodide moiety (JAPRUO, Antoniadis et al., 2005View full citation; ONOCOM, Agarwal, 2021View full citation).

To highlight the structural novelty of the title compound, it is compared with the closest discrete hepta­iodide analogues: hexa­kis­(2-hy­droxy­pyridine) bis­(2-hy­droxy­pyridinium) hemikis(iodide) sesquikis(hepta­iodide) diiodine (JAPRUO; Antoniadis et al., 2005View full citation) and 1,3-dimethyl-1H-imidazol-3-ium hepta­iodide (YUPXOY; Fei et al., 2015View full citation). It is also worth noting the already mentioned structure of [HMTAHD]3+[I7]3– (PEKKEX; Lin et al., 2012View full citation). The three compounds exhibit significant structural differences compared to the linear [I7]3– conformation of the title compound. In both JAPRUO and YUPXOY, the [I7]− anions adopt bent (zigzag or Z-type) shapes described as I2·I3−·I2 adducts featuring short I—I bonds typical for I2 subunits. The only other [I7]3– species, PEKKEX, shares the same I−·I2·I−·I2·I− sequence. However, this polyiodide anion shows a longer I2 covalent bond of 2.8127 (5) Å and adopts a V-shaped arrangement with an I⋯I⋯I angle of 136.22 (9)°.

5. Synthesis and crystallization

Ethyl­amine (0.5 mmol) was mixed with iodine (1 mmol) in 3 ml of 55%wt HI. The mixture was stirred for 4 h and then left to stand for one month. Black crystals formed during this period. The crystals were separated and stored under Paratone oil until the diffraction experiment.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. The I5 atom representing the isolated iodide anion is disordered over a special position with site symmetry 2/m and was refined with occupancies of 0.5 for I5A and 0.25 for I5B to ensure a total charge of −1. The ethyl­ammonium group N1—C1—C2 lies in a mirror plane; the hydrogen atoms attached to N1 and C2 are disordered around this mirror plane and were refined with an occupancy of 0.5 each. In the ethyl­ammonium group N2—C3—C4, the C4 atom lies on a mirror plane; atoms N2 and C3, as well as all H atoms bonded to them, are disordered about this mirror plane and thus were refined with an occupancy of 0.5. The H atoms were positioned geometrically and were allowed to ride on their parent atom with Uiso(H) = 1.5Ueq(C) for methyl H atoms, Uiso(H) = 1.2Ueq(C) for methyl­ene H atoms, and Uiso(H) = 1.2Ueq(N) for ammonium H atoms.

Table 3
Experimental details

Crystal data
Chemical formula 4C2H8N+·I73−·I−
Mr 1199.57
Crystal system, space group Monoclinic, C2/m
Temperature (K) 293
a, b, c (Å) 23.0274 (12), 7.0212 (3), 9.3382 (5)
β (°) 102.984 (5)
V (Å3) 1471.19 (13)
Z 2
Radiation type Mo Kα
μ (mm−1) 8.43
Crystal size (mm) 0.32 × 0.11 × 0.06
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, HyPix
Absorption correction Analytical [CrysAlis PRO (Rigaku OD, 2024View full citation) using a multifaceted crystal model based on expressions derived by Clark & Reid (1995View full citation)]
Tmin, Tmax 0.043, 0.491
No. of measured, independent and observed [I > 2σ(I)] reflections 10365, 2106, 1734
Rint 0.061
(sin θ/λ)max (Å−1) 0.711
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.089, 1.04
No. of reflections 2106
No. of parameters 78
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.87, −1.42
Computer programs: CrysAlis PRO (Rigaku OD, 2024View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation), OLEX2 (Dolomanov et al., 2009View full citation) and publCIF (Westrip, 2010View full citation).

Supporting information


Computing details top

Tetrakis(ethylammonium) heptaiodide(3-) iodide top
Crystal data top
4C2H8N+·I73−·I−F(000) = 1064
Mr = 1199.57Dx = 2.708 Mg m−3
Monoclinic, C2/mMo Kα radiation, λ = 0.71073 Å
a = 23.0274 (12) ÅCell parameters from 6780 reflections
b = 7.0212 (3) Åθ = 2.6–29.5°
c = 9.3382 (5) ŵ = 8.43 mm−1
β = 102.984 (5)°T = 293 K
V = 1471.19 (13) Å3Plate, clear light orange
Z = 20.32 × 0.11 × 0.06 mm
Data collection top
XtaLAB Synergy, Dualflex, HyPix
diffractometer
2106 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source1734 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.061
Detector resolution: 10.0000 pixels mm-1θmax = 30.4°, θmin = 2.6°
ω scansh = −32→30
Absorption correction: analytical
[CrysAlisPro (Rigaku OD, 2024) using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]
k = −9→9
Tmin = 0.043, Tmax = 0.491l = −12→12
10365 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0507P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.87 e Å−3
2106 reflectionsΔρmin = −1.42 e Å−3
78 parametersExtinction correction: SHELXL (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0059 (3)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I11.0000001.0000000.5000000.06616 (18)
I20.85877 (2)1.0000000.56630 (4)0.05694 (16)
I30.74738 (2)1.0000000.63002 (4)0.05321 (15)
I40.61406 (2)1.0000000.72342 (5)0.05892 (16)
I5A0.5000000.5000001.0000000.094 (2)0.5
I5B0.5000000.4245 (9)1.0000000.0607 (8)0.25
N10.61795 (17)0.5000000.8233 (5)0.0533 (10)
H1A0.6151580.6125080.7783320.064*0.5
H1B0.5850300.4786500.8557250.064*0.5
H1C0.6222140.4088410.7602060.064*0.5
N20.9570 (4)0.5833 (12)0.6813 (9)0.100 (3)0.5
H2D0.9297220.5797620.5970370.121*0.5
H2E0.9923630.5515540.6651690.121*0.5
H2F0.9587780.7003610.7186160.121*0.5
C10.6701 (2)0.5000000.9487 (6)0.0639 (14)
H1D0.6688000.3881991.0088900.077*0.5
H1E0.6688000.6118011.0088900.077*0.5
C20.7280 (3)0.5000000.8956 (8)0.0710 (17)
H2A0.7258860.4048390.8207710.107*0.5
H2B0.7607130.4722710.9764850.107*0.5
H2C0.7337460.6228900.8559070.107*0.5
C30.9410 (5)0.4524 (12)0.7824 (13)0.091 (3)0.5
H3A0.9692660.4610660.8764660.109*0.5
H3B0.9419480.3234290.7458380.109*0.5
C40.8785 (4)0.5000000.8011 (9)0.100 (3)
H4A0.8551370.5484980.7101930.150*0.5
H4B0.8810240.5944140.8765940.150*0.5
H4C0.8601450.3870210.8282820.150*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0375 (3)0.1007 (4)0.0587 (3)0.0000.0076 (2)0.000
I20.0554 (2)0.0580 (2)0.0585 (2)0.0000.01484 (16)0.000
I30.0537 (2)0.0511 (2)0.0544 (2)0.0000.01120 (15)0.000
I40.0477 (2)0.0455 (2)0.0861 (3)0.0000.02051 (18)0.000
I5A0.0704 (13)0.100 (5)0.125 (3)0.0000.0488 (14)0.000
I5B0.0613 (13)0.064 (3)0.0609 (14)0.0000.0225 (9)0.000
N10.045 (2)0.056 (2)0.059 (2)0.0000.0106 (18)0.000
N20.075 (5)0.138 (8)0.093 (6)0.018 (4)0.031 (4)0.039 (5)
C10.054 (3)0.077 (4)0.056 (3)0.0000.004 (2)0.000
C20.052 (3)0.069 (4)0.085 (4)0.0000.000 (3)0.000
C30.097 (7)0.064 (9)0.106 (7)−0.006 (5)0.010 (6)0.006 (5)
C40.130 (8)0.095 (5)0.089 (5)0.0000.054 (6)0.000
Geometric parameters (Å, º) top
I1—I23.4445 (4)N2—C31.423 (10)
I2—I32.7604 (6)C1—H1D0.9700
I3—I43.3747 (5)C1—H1E0.9700
I5A—I5B0.530 (6)C1—C21.522 (9)
I5A—I5Bi0.530 (6)C2—H2A0.9600
I5B—I5Bi1.061 (13)C2—H2B0.9600
N1—H1A0.8900C2—H2C0.9600
N1—H1B0.8900C3—H3A0.9700
N1—H1C0.8900C3—H3B0.9700
N1—C11.478 (6)C3—C41.525 (11)
N2—H2D0.8900C4—H4A0.9600
N2—H2E0.8900C4—H4B0.9600
N2—H2F0.8900C4—H4C0.9600
I3—I2—I1177.961 (16)C1—C2—H2A109.5
I2—I3—I4177.540 (16)C1—C2—H2B109.5
I5B—I5A—I5Bi180.0C1—C2—H2C109.5
I5A—I5B—I5Bi0.000 (2)H2A—C2—H2B109.5
H1A—N1—H1B109.5H2A—C2—H2C109.5
H1A—N1—H1C109.5H2B—C2—H2C109.5
H1B—N1—H1C109.5N2—C3—H3A109.9
C1—N1—H1A109.5N2—C3—H3B109.9
C1—N1—H1B109.5N2—C3—C4109.0 (7)
C1—N1—H1C109.5H3A—C3—H3B108.3
H2D—N2—H2E109.5C4—C3—H3A109.9
H2D—N2—H2F109.5C4—C3—H3B109.9
H2E—N2—H2F109.5C3ii—C4—C325.3 (6)
C3—N2—H2D109.5C3—C4—H4A109.5
C3—N2—H2E109.5C3ii—C4—H4A100.3
C3—N2—H2F109.5C3ii—C4—H4B91.8
N1—C1—H1D109.5C3—C4—H4B109.5
N1—C1—H1E109.5C3—C4—H4C109.5
N1—C1—C2110.9 (5)C3ii—C4—H4C134.0
H1D—C1—H1E108.0H4A—C4—H4B109.5
C2—C1—H1D109.5H4A—C4—H4C109.5
C2—C1—H1E109.5H4B—C4—H4C109.5
N2—C3—C4—C3ii−39.0 (8)
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···I40.892.773.6283 (12)163
N1—H1B···I5A0.892.623.481 (4)163
N1—H1B···I5B0.892.643.521 (4)170
N1—H1B···I5Bi0.892.703.521 (4)154
N1—H1C···I2iii0.893.233.794 (4)123
N1—H1C···I4iv0.892.893.6283 (12)141
N2—H2D···I4iii0.892.993.811 (8)155
N2—H2E···I4v0.892.763.597 (9)158
N2—H2F···I5Bvi0.893.033.775 (9)143
Symmetry codes: (i) −x+1, −y+1, −z+2; (iii) −x+3/2, y−1/2, −z+1; (iv) x, y−1, z; (v) x+1/2, y−1/2, z; (vi) x+1/2, y+1/2, z.
Selected structural parameters (Å, °)of the polyiodide anion top
I—I bondLengthI—I—IAngle
I1—I23.4445 (4)I1—I2—I3177.961 (16)
I2—I32.7604 (6)I2—I3—I4177.540 (16)
I3—I43.3747 (5)I2—I1—I2i180.0
Symmetry code: (i) 2 - x, y, 1 - z.
 

Acknowledgements

The authors are grateful to the FAIRE programme provided by the Cambridge Crystallographic Data Centre (CCDC) for the opportunity to use the Cambridge Structural Database (CSD) and associated software.

Funding information

Funding for this research was provided by: Ministry of Education and Science of Ukraine (grant No. 24BF037-02).

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