Crystal structure of a new hybrid compound based on an iodido­plumbate(II) anionic motif

Mokhnache, O.; Boughzala, H.

doi:10.1107/S2056989015023786

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Volume 72| Part 1| January 2016| Pages 56-59

doi:10.1107/S2056989015023786

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Crystal structure of a new hybrid compound based on an iodidoplumbate(II) anionic motif

Oualid Mokhnache ^a and Habib Boughzala ^a ^*

^aLaboratoire de Matériaux et Cristallochimie, Faculté des Sciences de Tunis, Université de Tunis El Manar, 2092 Manar II Tunis, Tunisia
^*Correspondence e-mail: habib.boughzala@ipein.rnu.tn

Edited by A. Van der Lee, Université de Montpellier II, France (Received 27 November 2015; accepted 10 December 2015; online 1 January 2016)

Crystals of the one-dimensional organic–inorganic lead iodide-based compound catena-poly[bis(piperazine-1,4-diium) [[tetraiodidoplumbate(II)]-μ-iodido] iodide monohydrate], (C₄N₂H₁₂)₂[PbI₅]I·H₂O, were obtained by slow evaporation at room temperature of a solution containing lead iodide and piperazine in a 1:2 molar ratio. Inorganic lead iodide chains, organic (C₄N₂H₁₂)²⁺ cations, water molecules of crystallization and isolated I⁻ anions are connected through N—H⋯·I, N—H⋯OW and OW—H⋯I hydrogen-bond interactions. Zigzag chains of corner-sharing [PbI₆]⁴⁻ octahedra with composition [PbI_4/1I_2/2]³⁻ running parallel to the a axis are present in the structure packing.

Keywords: crystal structure; organic–inorganic hybrid; iodidoplumbate(II); piperazine; 1-D hybrid compound.

CCDC reference: 1429047

1. Chemical context

Organic–inorganic hybrid materials offer the opportunity to combine the desirable properties of the organic moiety such as processability, toughness and impact strength with the typical properties of the inorganic part such as high temperature stability and durability. The opto-electronic characteristics of hybrid materials are closely related to the metal cluster size. In recent years, a significant number of organic–inorganic hybrid materials based on lead halide units have been prepared and studied (Billing & Lemmerer, 2006 ; Rayner & Billing, 2010 ), in particular with self-organized low-dimensional families of lead iodide-based crystals where the [PbI₆] octahedra form one-, two- or three-dimensional networks (Elleuch et al., 2007 ; Trigui et al., 2011 ). In one-dimensional lead halide hybrid compounds, the inorganic chains may be formed by one, two or three bridging halides, referred to as corner-, edge- and face-sharing polyhedra, respectively. Thanks to their anticipated electroluminescence, photoluminescence and non-linear optical properties, these compounds are the most desired ones (Lemmerer & Billing, 2006 ). Lead iodide-based hybrid materials are studied extensively for their excitonic and magneto-optical properties. In this work we report the synthesis and crystal structure determination of a new lead iodide hybrid, (C₄N₂H₁₂)₂[PbI₅]·I·H₂O, (I).

2. Structural commentary

The structural units of (I) consist of one piperazine molecule, one water molecule, one isolated iodine and one [PbI₆] unit (Fig. 1). The electrical neutrality is ensured by two organic molecules of doubly protonated piperazine.

Figure 1
Structural units of the title compound, showing the atom-numbering scheme. Atomic displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. [Symmetry codes: (i) x, $[{1\over 2}]$ − y, z; (ii) − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z.]

The main part of the inorganic moiety is composed by the lead Pb²⁺ cation which adopts a distorted octahedral coordination. The angles between cis-related I⁻ ions range from 85.022 (12) to 96.89 (3)° at most, whereas the trans angles deviate from 180° by 12.95 (3)° (Table 1). Two adjacent corners connect the [PbI₆] octahedron to its neighbours, leading to zigzag chains running parallel to the a axis (Fig. 2). This one-dimensional anionic network leaves empty spaces in which the organic cations are located. The [PbI₆] octahedra establish two strong hydrogen bonds (Table 2), N2—H4N⋯I3 and N2ⁱ—H4Nⁱ⋯I3, via the I3 corners [symmetry code: (i) x, $[{1\over 2}]$ − y, z] as illustrated in Fig. 3.

Table 1
Selected geometric parameters (Å, °)

Pb—I2	3.0689 (9)	Pb—I4	3.2396 (9)
Pb—I3	3.1511 (9)	Pb—I4ⁱⁱ	3.3535 (9)
Pb—I1	3.2173 (8)	I4—Pbⁱⁱⁱ	3.3535 (9)
Pb—I1ⁱ	3.2173 (8)	OW—HW2	0.86 (2)

I2—Pb—I3	96.06 (3)	I1—Pb—I4	87.185 (13)
I2—Pb—I1	85.021 (12)	I1ⁱ—Pb—I4	87.185 (13)
I3—Pb—I1	93.943 (13)	I2—Pb—I4ⁱⁱ	179.99 (3)
I2—Pb—I1ⁱ	85.022 (12)	I3—Pb—I4ⁱⁱ	83.95 (3)
I3—Pb—I1ⁱ	93.944 (13)	I1—Pb—I4ⁱⁱ	94.978 (12)
I1—Pb—I1ⁱ	167.89 (2)	I1ⁱ—Pb—I4ⁱⁱ	94.977 (12)
I2—Pb—I4	96.89 (3)	I4—Pb—I4ⁱⁱ	83.105 (14)
I3—Pb—I4	167.05 (3)	Pb—I4—Pbⁱⁱⁱ	178.91 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯OW^iv	0.90	2.05	2.874 (5)	155
N1—H2N⋯I5^v	0.90	2.69	3.543 (4)	160
N2—H4N⋯I3	0.90	2.85	3.656 (4)	151
OW—HW1⋯I5^vi	0.86	2.74	3.477 (5)	145
Symmetry codes: (iv) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Figure 2
The [PbI_4/1I_2/2]³⁻ chain of (I)

running parallel to the a-axis direction and exhibiting a zigzag conformation.

Figure 3
Linkage around one [PbI₆] octahedron formed by two similar octahedra and two protonated piperazine cations. Hydrogen bonds are drawn as dashed green lines. [Symmetry codes: (i) x, $[{1\over 2}]$ − y, z; (ii) − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z.]

The second part of the inorganic moiety contains a water molecule and the iodide anion I5 linked by a strong hydrogen-bond interaction (Table 2). Both are located in the same layers in which the [PbI₆] octahedra are located. As shown in Fig. 4, the anion I5 is linked to one water molecule by I5⋯HW1ⁱ–OWⁱ [symmetry code: (i) 1 − x, $[{1\over 2}]$ + y, 1 − z] and two organic cations via I5⋯H2Nⁱⁱ—N1ⁱⁱ and I5⋯H2Nⁱⁱⁱ—N1ⁱⁱⁱ [symmetry codes: (ii) $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ − z; (iii) $[{1\over 2}]$ + x, y, $[{1\over 2}]$ − z]. On the other hand, the water molecule is associated to one iodine (I5) via OW—HW1⋯I5ⁱⁱⁱ [symmetry code: (iii) 1 − x, − $[{1\over 2}]$ + y, 1 − z) and to two piperazinium cations via OW⋯H1Nⁱⁱ—N1ⁱⁱ and OW⋯H1Nⁱ—N1ⁱ (Fig. 5). In this configuration, no acceptor was found for HW2 and H3N.

Figure 4
Hydrogen-bonding interactions with isolated iodide in (I)

. [Symmetry codes: (i) 1 − x, $[{1\over 2}]$ + y, 1 − z; (ii) $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ − z; (iii) $[{1\over 2}]$ + x, y, $[{1\over 2}]$ − z.]

Figure 5
Water molecule hydrogen bonding interactions in (I)

. [Symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 − x, − $[{1\over 2}]$ + y, 1 − z.]

The six-membered piperazinium cation ring adopts a chair conformation. It interacts with the inorganic chain via strong N2—H4N⋯I3 hydrogen bonds with a 2.85 Å bond length (Table 2 and Fig. 6). In the crystal structure, the piperazinium cations are also linked to the water molecule by an N1—H1N⋯OWⁱⁱⁱ hydrogen bond and to the iodine anion by N1—H2N⋯I5ⁱⁱⁱ hydrogen bonds.

Figure 6
The hydrogen bonding environment of the cation of the title compound. [Symmetry codes: (i) − $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ − z; (ii) − $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, $[{1\over 2}]$ − z; (iii) 1 − x, $[{1\over 2}]$ + y, 1 − z.]

Compared to its homologous hybrids, the structure of the title compound exhibits an original arrangement of the inorganic layers. It is composed by two parts: the first are the [PbI₆] octahedra sharing adjacent corners and so assembling into chains running along the [100] direction. The second original feature is the structural cohesion by water molecules and isolated iodide anions. This structural arrangement will probably have an impact on the dielectric behavior of the material. Luminescence and UV–visible spectroscopy measurements of this compound, coupled to theoritical calculation of the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) electronic transitions are in progress.

As shown in Fig. 7, the structure of (I) is self-assembled into alternating organic and inorganic layers parallel to the ac plane. The organic part is made up of (C₄H₁₂N₂)²⁺ cations located in the voids around the corner-sharing [PbI₆]⁴⁻ octahedra. The iodine anions and the water molecules connect the organic and inorganic sheets by strong hydrogen-bond interactions.

Figure 7
A packing diagram of (I)

, viewed along the a axis showing the alternating organic and inorganic layers. Hydrogen bonds are omitted for clarity.

4. Database survey

Using the piperazine-1,4-diium cation scheme in the similarity option of the WEBCSD interface (Groom & Allen, 2014 ), more than 90 records are found in the CCDC database. Only 24 are inorganic–organic hybrid compounds with several metals Cu, Zn, Co, Bi, Cd, Sb, Au etc. The closest chemical composition found is a bismuth-based compound (II): (C₄N₂H₁₂)₂[BiCl₆]·Cl·H₂O (Gao et al., 2011 ). In spite of the chemical formula similarity, it seems that the orthorhombic (Pnma) title structure is much more regular than the monoclinic (P2₁/c) compound (II) with approximately the same cell volume, where the small difference is probably due to the chlorine/iodine substitution. In contrast to the structure of (I), the anionic network in the structure of (II) is 0-D, built up by isolated [BiCl₆] octahedra. The water molecule and the isolated halogen play, in both cases, the same crucial role in the structural cohesion, linking the anionic part to the organic moieties.

5. Synthesis and crystallization

Crystals of the title compound were prepared by slow evaporation at room temperature by mixing 1,4-diazacyclohexane (C₄H₁₀N₂) (2 mol) with a solution of lead iodide PbI₂ (1 mol) in an equimolar mixture of ethanol and DMF. After several weeks, the obtained crystals were isolated and dried.

6. Refinement

Data collection and structure refinement details are summarized in Table 3. Hydrogen atoms were placed using geometrical constraints using adequate HFIX instructions (SHELXL) and refined with AFIX instructions. Water hydrogen atoms were found in Fourier difference maps and O—H distances were restrained using DFIX (0.86 Å) and DANG instructions.

Table 3
Experimental details

Crystal data
Chemical formula	(C₄H₁₂N₂)₂[PbI₅]I·H₂O
M_r	1162.92
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	298
a, b, c (Å)	8.7477 (10), 13.488 (2), 20.336 (3)
V (Å³)	2399.4 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	14.75
Crystal size (mm)	0.45 × 0.14 × 0.10

Data collection
Diffractometer	Enfar–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968 )
T_min, T_max	0.622, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	3601, 2729, 1941
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.086, 1.05
No. of reflections	2729
No. of parameters	105
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.00, −1.28
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994 ), XCAD4 (Harms & Wocadlo, 1995 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2006 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1429047

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015023786/vn2104sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015023786/vn2104Isup2.hkl

checkCIF report

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[bis(piperazine-1,4-diium) [[tetraiodidoplumbate(II)]-µ-iodido] iodide monohydrate] top

Crystal data top

(C₄H₁₂N₂)₂[PbI₅]I·H₂O	D_x = 3.219 Mg m⁻³
M_r = 1162.92	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 25 reflections
a = 8.7477 (10) Å	θ = 13.7–14.7°
b = 13.488 (2) Å	µ = 14.75 mm⁻¹
c = 20.336 (3) Å	T = 298 K
V = 2399.4 (6) Å³	Prism, yellow
Z = 4	0.45 × 0.14 × 0.10 mm
F(000) = 2040

Data collection top

Enfar–Nonius CAD-4 diffractometer	R_int = 0.034
Radiation source: fine-focus sealed tube	θ_max = 27.0°, θ_min = 2.0°
ω/2τ scans	h = −11→2
Absorption correction: ψ scan (North et al., 1968)	k = −1→17
T_min = 0.622, T_max = 0.999	l = −1→25
3601 measured reflections	2 standard reflections every 120 min
2729 independent reflections	intensity decay: −1%
1941 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0358P)² + 1.6589P] where P = (F_o² + 2F_c²)/3
2729 reflections	(Δ/σ)_max < 0.001
105 parameters	Δρ_max = 2.00 e Å⁻³
3 restraints	Δρ_min = −1.28 e Å⁻³

Special details top

Experimental. Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Pb	0.70782 (5)	0.2500	0.37128 (2)	0.02909 (13)
I1	0.74558 (6)	0.48720 (5)	0.37511 (3)	0.03537 (16)
I2	0.94306 (9)	0.2500	0.48324 (4)	0.0367 (2)
I3	0.41658 (9)	0.2500	0.46247 (4)	0.0410 (2)
I4	0.95081 (10)	0.2500	0.25107 (4)	0.0421 (2)
I5	0.54190 (11)	0.7500	0.19255 (5)	0.0489 (3)
N1	0.3401 (9)	0.5979 (6)	0.3685 (3)	0.0430 (19)
H1N	0.2673	0.6433	0.3635	0.052*
H2N	0.4301	0.6287	0.3680	0.052*
N2	0.1611 (9)	0.4232 (6)	0.3784 (3)	0.0407 (19)
H3N	0.0691	0.3951	0.3792	0.049*
H4N	0.2305	0.3754	0.3828	0.049*
C1	0.3329 (10)	0.5257 (8)	0.3131 (4)	0.039 (2)
H1A	0.3455	0.5604	0.2716	0.046*
H1B	0.4151	0.4779	0.3172	0.046*
C2	0.1836 (9)	0.4737 (7)	0.3138 (4)	0.035 (2)
H2A	0.1805	0.4252	0.2787	0.042*
H2B	0.1019	0.5210	0.3066	0.042*
C3	0.3199 (10)	0.5469 (8)	0.4320 (4)	0.041 (2)
H3A	0.4040	0.5012	0.4389	0.050*
H3B	0.3214	0.5953	0.4672	0.050*
C4	0.1744 (10)	0.4919 (8)	0.4337 (4)	0.046 (3)
H4A	0.1677	0.4552	0.4746	0.055*
H4B	0.0900	0.5386	0.4325	0.055*
OW	0.4301 (11)	0.2500	0.6369 (5)	0.051 (3)
HW1	0.393 (13)	0.2500	0.676 (2)	0.080*
HW2	0.352 (9)	0.2500	0.612 (4)	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb	0.0224 (2)	0.0364 (3)	0.0284 (2)	0.000	0.00002 (19)	0.000
I1	0.0287 (3)	0.0386 (4)	0.0388 (3)	0.0019 (2)	−0.0011 (2)	0.0008 (3)
I2	0.0322 (4)	0.0408 (6)	0.0372 (4)	0.000	−0.0079 (4)	0.000
I3	0.0296 (4)	0.0498 (6)	0.0435 (4)	0.000	0.0088 (4)	0.000
I4	0.0353 (4)	0.0420 (5)	0.0491 (5)	0.000	0.0180 (4)	0.000
I5	0.0525 (5)	0.0392 (6)	0.0550 (5)	0.000	0.0114 (5)	0.000
N1	0.030 (4)	0.042 (5)	0.058 (5)	−0.007 (4)	−0.009 (4)	0.002 (4)
N2	0.044 (4)	0.032 (4)	0.046 (4)	−0.009 (4)	−0.008 (4)	0.006 (4)
C1	0.039 (5)	0.051 (6)	0.025 (4)	−0.002 (5)	−0.001 (4)	0.005 (4)
C2	0.031 (4)	0.035 (5)	0.040 (5)	0.002 (4)	−0.004 (4)	−0.005 (4)
C3	0.035 (5)	0.046 (6)	0.043 (5)	0.000 (5)	0.001 (4)	−0.015 (5)
C4	0.029 (5)	0.067 (8)	0.041 (5)	−0.009 (5)	0.008 (4)	−0.012 (5)
OW	0.046 (6)	0.038 (6)	0.068 (6)	0.000	−0.003 (5)	0.000

Geometric parameters (Å, º) top

Pb—I2	3.0689 (9)	N2—H4N	0.8900
Pb—I3	3.1511 (9)	C1—C2	1.483 (11)
Pb—I1	3.2173 (8)	C1—H1A	0.9700
Pb—I1ⁱ	3.2173 (8)	C1—H1B	0.9700
Pb—I4	3.2396 (9)	C2—H2A	0.9700
Pb—I4ⁱⁱ	3.3535 (9)	C2—H2B	0.9700
I4—Pbⁱⁱⁱ	3.3535 (9)	C3—C4	1.473 (12)
N1—C1	1.490 (11)	C3—H3A	0.9700
N1—C3	1.474 (11)	C3—H3B	0.9700
N1—H1N	0.8900	C4—H4A	0.9700
N1—H2N	0.8900	C4—H4B	0.9700
N2—C4	1.462 (11)	OW—HW1	0.86 (2)
N2—C2	1.493 (10)	OW—HW2	0.86 (2)
N2—H3N	0.8900

I2—Pb—I3	96.06 (3)	H3N—N2—H4N	107.9
I2—Pb—I1	85.021 (12)	C2—C1—N1	109.8 (7)
I3—Pb—I1	93.943 (13)	C2—C1—H1A	109.7
I2—Pb—I1ⁱ	85.022 (12)	N1—C1—H1A	109.7
I3—Pb—I1ⁱ	93.944 (13)	C2—C1—H1B	109.7
I1—Pb—I1ⁱ	167.89 (2)	N1—C1—H1B	109.7
I2—Pb—I4	96.89 (3)	H1A—C1—H1B	108.2
I3—Pb—I4	167.05 (3)	C1—C2—N2	110.0 (7)
I1—Pb—I4	87.185 (13)	C1—C2—H2A	109.7
I1ⁱ—Pb—I4	87.185 (13)	N2—C2—H2A	109.7
I2—Pb—I4ⁱⁱ	179.99 (3)	C1—C2—H2B	109.7
I3—Pb—I4ⁱⁱ	83.95 (3)	N2—C2—H2B	109.7
I1—Pb—I4ⁱⁱ	94.978 (12)	H2A—C2—H2B	108.2
I1ⁱ—Pb—I4ⁱⁱ	94.977 (12)	C4—C3—N1	111.1 (7)
I4—Pb—I4ⁱⁱ	83.105 (14)	C4—C3—H3A	109.4
Pb—I4—Pbⁱⁱⁱ	178.91 (3)	N1—C3—H3A	109.4
C1—N1—C3	110.7 (7)	C4—C3—H3B	109.4
C1—N1—H1N	109.5	N1—C3—H3B	109.4
C3—N1—H1N	109.5	H3A—C3—H3B	108.0
C1—N1—H2N	109.5	N2—C4—C3	111.6 (7)
C3—N1—H2N	109.5	N2—C4—H4A	109.3
H1N—N1—H2N	108.1	C3—C4—H4A	109.3
C4—N2—C2	112.1 (7)	N2—C4—H4B	109.3
C4—N2—H3N	109.2	C3—C4—H4B	109.3
C2—N2—H3N	109.2	H4A—C4—H4B	108.0
C4—N2—H4N	109.2	HW1—OW—HW2	104 (3)
C2—N2—H4N	109.2

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···OW^iv	0.90	2.05	2.874 (5)	155
N1—H2N···I5^v	0.90	2.69	3.543 (4)	160
N2—H4N···I3	0.90	2.85	3.656 (4)	151
OW—HW1···I5^vi	0.86	2.74	3.477 (5)	145

Symmetry codes: (iv) −x+1, y+1/2, −z+1; (v) x−1/2, −y+3/2, −z+1/2; (vi) −x+1, y−1/2, −z+1.

References

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