Metal halide coordination compounds with quinazolin-4(3H)-one

Turgunov, K.K.; Englert, U.

doi:10.1107/S2056989023004802

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ISSN: 2056-9890

Volume 79| Part 7| July 2023| Pages 614-618

https://doi.org/10.1107/S2056989023004802

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Metal halide coordination compounds with quinazolin-4(3H)-one

Kambarali K. Turgunov ^a,^b ^* and Ulli Englert ^c

^aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan, ^bTurin Polytechnic University in Tashkent, Kichik Khalka yuli str. 17, 100095 Tashkent, Uzbekistan, and ^cInstitute of Inorganic Chemistry, RWTH Aachen University, Landoltweg 1, 52056, Aachen, Germany
^*Correspondence e-mail: kambarali@mail.ru

Edited by M. Weil, Vienna University of Technology, Austria (Received 3 April 2023; accepted 2 June 2023; online 6 June 2023)

Three coordination compounds of quinazolin-4(3H)-one (quinoz; C₈H₆N₂O) with divalent group 12 halides are reported. In all complexes, coordination occurs via the nitrogen atom ortho to the quinazolinone carbonyl group. In the two chain polymers with composition [MX₂(quinoz)], viz. (M = Cd, X = Br), catena-poly[[[quinazolin-4(3H)-one-κN³]cadmium(II)]-di-μ-bromido], [CdBr₂(C₈H₆N₂O)]_n (I), and M = Hg, X = Cl, catena-poly[[[quinazolin-4(3H)-one-κN³]mercury(II)]-di-μ-chlorido], [HgCl₂(C₈H₆N₂O)]_n (II), the divalent cations are five-coordinate, with four bridging halide and one terminal quinoz ligand. The Cd^II atom in (I) has an almost trigonal–bipyramidal coordination environment, whereas the Hg^II atom in (II) has a more distorted coordination environment. Likewise, the halide bridges in (II) are significantly more asymmetric than in (I). In both (I) and (II), quinoz ligands at adjacent cations along each strand are oriented in opposite directions, and the organic ligands of neighboring strands interdigitate with resulting π–π interactions. In contrast to the halide-bridged chain polymers (I) and (II), the adduct of quinoz with CdI₂ is the tetrahedral complex [CdI₂(quinoz)₂], diiodidobis[quinazolin-4(3H)-one-κN³]cadmium(II), [CdI₂(C₁₆H₁₂N₄O₂)], (III). The Cd^II atom in this discrete complex is located on a twofold rotation axis. Disorder in (III) is reflected in an alternative minority orientation of the molecules for which the iodine sites closely match the position of the majority orientation. In view of the low site occupancy of only 0.0318 (8) Å, only the Cd^II position for this alternative orientation was taken into account during refinement. In all three compounds, classical N—H⋯O hydrogen bonds with donor–acceptor distances of ca 2.9 Å occur; they link the polymer chains in (I) and (II) into di-periodic networks and connect adjacent discrete complexes in (III) to mono-periodic strands.

Keywords: crystal structure; cadmium(II) coordination polymer; halide-bridged coordination polymers; mercury(II) coordination polymer; quinazolinone coordination; tetrahedral cadmium(II) complex..

CCDC references: 2267121; 2267120; 2267119

1. Chemical context

4(3H)-Quinazolinone (quinoz) can act as ligand for metal ions in different coordination modes. Both coordination through the nitrogen atom para (mode 1) and, after tautomerization, via the nitrogen atom ortho to the quinazolinone carbonyl group (mode 2) have been observed (Fig. 1). An Ag^I coordination compound (Li et al., 2015 ) provides an example for the co-existence of both binding modes in the same crystal structure. Earlier studies on the reaction products of cadmium chloride or bromide with quinazolin-4(3H)-one have shown that the quinoz ligand may interact with Cd^II cations via the para nitrogen atom, i.e. according to mode 1. Four bridging halides in the equatorial plane and two quinoz ligands in a trans-axial arrangement give rise to a pseudo-octahedral coordination environment around the metal cation (Turgunov & Englert, 2010 ; Turgunov et al., 2010 ; Shomurotova et al., 2012 ; Đaković et al., 2018 ).

Figure 1
The two possible types of coordination modes for the quinazolin-4-one ligand in metal complexes.

We here report three other examples for coordination according to mode 2, namely the adducts of quinoz with CdBr₂ (I), HgCl₂ (II) and CdI₂ (III). The influence of different halide ligands on the coordination environment of divalent cations with N-donor co-ligands has been discussed in detail (Hu & Englert, 2001 , 2002 ; Hu et al., 2003 ).

2. Structural commentary

The asymmetric unit of (I) consists of a Cd^II cation, two Br⁻ ligands and one quinoz ligand attached in mode 2 (Fig. 2). The cation adopts a coordination number of 5 and is characterized by a τ₅ descriptor (Addison et al., 1984 ) of 0.80. In an alternative description (Holmes, 1984 ), its shape corresponds to only 5% distorsion along a hypothetical pathway from D_3h to C_4v. Both qualifiers consistently assign this shape as trigonal bipyramidal, with the quinoz ligand in an equatorial position. The equatorial plane defined by Cd1, Br1, Br2ⁱ [symmetry code: (i) −x, 1 − y, 1 − z] and N3 and the least-squares plane through the quinoz ligand subtend a dihedral angle of 38.32 (13)°. The bromido ligands act as rather symmetric bridges between neighboring cations, thus giving rise to a chain polymer extending along [010]. Additional details concerning the crystal structure of (I) are best discussed together with the related derivative (II) (Fig. 3). Both compounds share the same composition [MX₂(quinoz)], with bridging halide ligands between neighboring divalent group 12 cations at a distance slightly less than 4 Å. The mercury compound (II) shows a considerably more distorted coordination environment than its cadmium congener (I): On the one hand, the coordination environment about the cation is less regular; both the τ₅ (0.56) and the Holmes descriptor (23%) assign a shape in-between trigonal bipyramidal and square pyramidal. On the other hand, the chlorido bridges in (II) are significantly more asymmetric than the bromido linkers in (I). Even more asymmetric halide bridges have been observed in the bis adduct of 1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-9-one to HgCl₂ (Turgunov et al., 2011 ). Both chain polymers (I) and (II) fit well into the wider context of halide-bridged chain polymers. The adducts of donor ligands to CdBr₂ or HgCl₂ mostly display coordination numbers of 5 or 6 and have bridging halide ligands. For such bromido-bridged Cd^II strands, similar Cd–Cd separations as in (I) [Cd1⋯Cd1ⁱ = 3.8667 (10) and Cd1⋯Cd1ⁱⁱ = 3.9051 (10) Å; symmetry codes: (i) −x, 2 − y, 1 − z; (ii) −x, 1 − y, 1 − z] have been reported (Hu & Englert, 2002; Merkens et al., 2014 ; Hu et al., 2003). The Hg–Hg separations [Hg1⋯Hg1ⁱ = 3.7881 (6) and Hg1⋯Hg1ⁱⁱ = 3.8827 (6) Å, symmetry codes: (i) 2 − x, 1 − y, −z; (ii) 2 − x, −y, −z] in (II) are comparable to those encountered in related chlorido-bridged polymers (Hu et al., 2007 ; Truong et al., 2017 ; van Terwingen et al., 2021 ; Merkens et al., 2010 ). A different situation arises for (III) (Fig. 4): for the bis(ligand) adduct of CdI₂, a discrete complex may be expected and is indeed encountered. The CSD database (Groom et al., 2016 ) contains only a few structures for six-coordinated Cd with four iodido and two additional arbitrary ligands, for example a di-periodic structure with bipyridyl ligands in one and iodido bridges in a second direction (Hu et al., 2003). In contrast, more than 600 hits for tetrahedrally coordinated Cd^II with two iodido and two additional ligands have been documented, and (III) falls into this category. The crystal structure of (III) has been previously reported by Đaković et al. (2018). Our present report takes a minor disorder into account, which explains an otherwise unaccounted high residual electron density; details are provided in the Refinement section. In (III), the cation resides on a twofold rotation axis of space group C2/c, Wyckoff position 4e. Its coordination environment is characterized by a τ₄ descriptor (Yang et al., 2007 ) of 0.93, corresponding to an almost undistorted tetrahedron.

Figure 2
Section of polymer (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level, H atoms are shown as spheres of arbitrary radius. [Symmetry codes: (i) −x, 1 − y, 1 − z; ii) −x, 2 − y, 1 − z; iii) x, 1 + y, z].

Figure 3
Section of polymer (II) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level, H atoms are shown as spheres of arbitrary radius. [Symmetry code: (i) 2 − x, 1 − y, −z].

Figure 4
Molecular structure of (III) with the atom-numbering scheme; the minor disorder of the Cd site is shown in Fig. 9

and has been omitted here. Displacement ellipsoids are drawn at the 50% probability level, H atoms are shown as spheres of arbitrary radius. [Symmetry code: (i) −x, y, $[{1\over 2}]$ − z]

3. Supramolecular features

Classical N—H⋯O hydrogen bonds exist in structures (I)–(III). They link the NH group to the carbonyl oxygen atom of a neighboring quinoz ligand [parallel to [001] for (I) and (II), and parallel to [010] for (III)], and involve donor–acceptor distances around 2.9 Å. Numerical details of the hydrogen-bonding interactions are compiled in Tables 1–3 . In the coordination polymers (I) and (II), quinoz ligands of adjacent strands interdigitate. The distances between neighboring coplanar organic ligands amount to one half of the lattice parameter b, i.e. 3.5–3.6 Å and suggest π–π stacking. As an example, a space-filling model for (I) (Fig. 5) shows the close approach between organic quinoz ligands on neighboring strands. An analysis with PLATON (Spek, 2020 ) gives numerical values of π–π stacking interactions observed between two parallel quinoz ligands for crystals of (I)–(III): Cg(pyrimidine ring)⋯Cg(benzene ring) distances are 3.6923 (3) Å (slippage 0.843 Å) and 3.718 (3) Å (0.906 Å) in (I), 3.7042 (4) Å (1.003 Å) in (II) and 3.5578 (14) Å (1.185 Å) in (III) (Figs. 6–8 ).

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.87 (3)	2.10 (3)	2.917 (6)	155 (6)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.89 (4)	2.11 (4)	2.935 (8)	155 (7)
Symmetry code: (i) .

Table 3
Hydrogen-bond geometry (Å, °) for (III)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.93 (3)	1.97 (3)	2.893 (3)	168 (4)
Symmetry code: (i) .

Figure 5
Space-filling model for (I) (PLUTO; Spek 2009

) as viewed along [100]; Br atoms have been omitted. Color code: Cd green, C black, O red, N blue, H white.

Figure 6
The relevant π–π interactions in the crystal structure of (I).

Figure 7
The relevant π–π interactions in the crystal structure of (II).

Figure 8
The relevant π–π interactions in the crystal structure of (III).

4. Synthesis and crystallization

Compound (I). 70 mg (0.2 mmol) of cadmium bromide tetrahydrate were dissolved in a mixture of 4 ml of ethanol and 1 ml of water. 60 mg (0.4 mmol) of quinazolin-4(3H)-one dissolved in 5 ml of ethanol were added to the cadmium bromide solution. Crystals started to precipitate after a few minutes, and colorless prismatic crystals suitable for single-crystal X-ray diffraction analysis formed within 2–3 h.

Compound (II). 54.3 mg (0.2 mmol) of HgCl₂ were dissolved in ∼3 ml acetone. 30 mg (0.2 mmol) of quinazolin-4(3H)-one were dissolved in 3 ml of acetone under mild heating, and the resulting solution was added to the HgCl₂ solution. Colorless prismatic crystals suitable for X-ray diffraction analysis formed within seconds.

Compound (III): 73 mg (0.2 mmol) of CdI₂ were dissolved in 1 ml of ethanol. 60 mg (0.4 mmol) of the ligand were dissolved in 4 ml of ethanol under mild heating, and the resulting solution was added to the CdI₂ solution. After slow evaporation of the solvent at ambient temperature for several days, colorless single crystals suitable for X-ray diffraction analysis were obtained.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. Positional parameters for H atoms attached to N atoms were refined, H atoms bonded to carbon were introduced in calculated positions and treated as riding on their parent atoms.

Table 4
Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	[CdBr₂(C₈H₆N₂O)]	[HgCl₂(C₈H₆N₂O)]	[CdI₂(C₁₆H₁₂N₄O₂)]
M_r	418.37	417.64	658.50
Crystal system, space group	Monoclinic, P2₁/c	Triclinic, P $[\overline{1}]$	Monoclinic, C2/c
Temperature (K)	100	100	100
a, b, c (Å)	10.7930 (11), 7.2019 (7), 13.7605 (14)	6.8191 (8), 7.0735 (8), 10.4659 (12)	22.242 (3), 6.8450 (9), 13.3702 (17)
α, β, γ (°)	90, 100.4705 (18), 90	85.718 (2), 80.7887 (19), 89.152 (2)	90, 118.8220 (16), 90
V (Å³)	1051.79 (18)	496.92 (10)	1783.4 (4)
Z	4	2	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	9.64	15.99	4.70
Crystal size (mm)	0.25 × 0.10 × 0.05	0.04 × 0.03 × 0.03	0.12 × 0.10 × 0.04

Data collection
Diffractometer	Bruker D8 gonimeter with APEX CCD detector	Bruker D8 gonimeter with APEX CCD detector	Bruker D8 gonimeter with APEX CCD detector
Absorption correction	Multi-scan (TWINABS; Bruker, 2014 )	Multi-scan (TWINABS; Bruker, 2014)	Multi-scan (SADABS; Bruker, 2014)
T_min, T_max	0.446, 0.746	0.302, 0.433	0.544, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	65521, 5868, 4717	14434, 5037, 4693	13210, 2687, 2519
R_int	0.089	0.050	0.024
(sin θ/λ)_max (Å⁻¹)	0.718	0.709	0.717

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.076, 1.04	0.036, 0.076, 1.08	0.026, 0.063, 1.12
No. of reflections	5868	5037	2687
No. of parameters	132	132	119
No. of restraints	1	1	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.96	1.54, −1.49	3.17, −0.50
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), PLATON (Spek, 2020) and publCIF (Westrip, 2010 ).

Several crystals of (I) were tested and proved to be twinned; two domains of roughly equal volume are related by a 180° rotation about the c axis. The specimen selected for intensity data collection showed ca 12000 overlapped out of a total of 65000 reflections. Final refined component fractions amounted to 0.5569 (8):0.4431 (8). Crystals of (II) were also twinned by non-merohedry. Here, two domains of roughly equal volume are related by a 180° rotation about the b axis. In the selected crystal, two domains contributed to ca 2000 overlapped out of a total of ca 14000 reflections. Final refined component fractions amounted to 0.5178 (9):0.4822 (9). The crystal selected for intensity data collection for (III) was a single crystal. After completion of the structure model, a difference-Fourier map showed a local density maximum of ca 5 electrons/ Å³ not associated with any atom site. This position subtended distances to the iodine atoms similar to Cd1—I1. We suggest that this residual electron density represents an alternative Cd site. In the final refinement, the sum of the site occupancies for the positionally disordered Cd sites was constrained to unity, and both sites were constrained to share the same anisotropic displacement parameters. Fig. 9 explains the arrangement of the molecules in both alternative orientations; the minority orientation is depicted in magenta. As the minority Cd site refined to an occupancy of only 0.0318 (8) and the iodine ligands for both orientations closely overlap, no attempt was made to detect and refine the alternative sites for the light atoms associated with the quinoz ligand. Interestingly, the authors of the previous crystal-structure determination of (III) (Đaković et al., 2018) encountered the same local density maximum (but without modeling the disorder). Hence, the disorder appears to be a feature of the crystal structure and not of the individual crystal chosen for the data collection.

Figure 9
Disorder in (III). The alternative Cd site (Cd2) is shown as a magenta-colored sphere. For clarity, the alternative ligand orientations are also shown in magenta. However, they have not been revealed experimentally and were not taken into account during refinement.

Supporting information

CCDC references: 2267121; 2267120; 2267119

Crystal structure: contains datablocks I, II, III, GLOBAL. DOI: https://doi.org/10.1107/S2056989023004802/wm5681sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023004802/wm5681Isup5.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023004802/wm5681IIsup6.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023004802/wm5681IIIsup7.hkl

checkCIF report

Computing details top

For all structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

catena-Poly[[[quinazolin-4(3H)-one-κN³]cadmium(II)]-di-µ-bromido] (I) top

Crystal data top

[CdBr₂(C₈H₆N₂O)]	F(000) = 776
M_r = 418.37	D_x = 2.642 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.7930 (11) Å	Cell parameters from 3537 reflections
b = 7.2019 (7) Å	θ = 3.0–26.0°
c = 13.7605 (14) Å	µ = 9.64 mm⁻¹
β = 100.4705 (18)°	T = 100 K
V = 1051.79 (18) Å³	Rod, colourless
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection top

Bruker D8 gonimeter with APEX CCD detector diffractometer	5868 independent reflections
Radiation source: Incoatec microsource	4717 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.089
ω scans	θ_max = 30.7°, θ_min = 3.0°
Absorption correction: multi-scan (TWINABS; Bruker, 2014)	h = −15→14
T_min = 0.446, T_max = 0.746	k = 0→10
65521 measured reflections	l = 0→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.026P)² + 1.8P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
5868 reflections	Δρ_max = 1.13 e Å⁻³
132 parameters	Δρ_min = −0.96 e Å⁻³
1 restraint

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.

Refinement. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
Cd1	0.06536 (3)	0.75144 (5)	0.52545 (2)	0.01158 (8)
Br1	−0.12368 (4)	0.94278 (7)	0.57455 (4)	0.01378 (11)
Br2	−0.01900 (5)	0.45101 (7)	0.63243 (4)	0.01525 (11)
O1	0.3587 (3)	0.7297 (5)	0.5233 (3)	0.0182 (8)
N1	0.3312 (4)	0.7386 (6)	0.8091 (3)	0.0145 (8)
H1	0.315 (6)	0.738 (8)	0.869 (2)	0.029 (17)*
C2	0.2323 (4)	0.7393 (7)	0.7372 (4)	0.0138 (9)
H2	0.151110	0.739229	0.754639	0.017*
N3	0.2391 (4)	0.7401 (6)	0.6423 (3)	0.0122 (8)
C4	0.3551 (4)	0.7349 (7)	0.6125 (4)	0.0126 (9)
C4A	0.4672 (4)	0.7350 (7)	0.6901 (4)	0.0117 (9)
C5	0.5890 (5)	0.7309 (7)	0.6692 (4)	0.0175 (10)
H5	0.600677	0.726430	0.602429	0.021*
C6	0.6918 (5)	0.7333 (8)	0.7441 (4)	0.0197 (11)
H6	0.774211	0.731509	0.728953	0.024*
C7	0.6761 (5)	0.7385 (8)	0.8425 (4)	0.0199 (11)
H7	0.747907	0.741545	0.893885	0.024*
C8	0.5571 (5)	0.7391 (8)	0.8656 (4)	0.0187 (11)
H8	0.546255	0.739904	0.932618	0.022*
C8A	0.4523 (4)	0.7384 (7)	0.7886 (3)	0.0122 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01016 (15)	0.01311 (15)	0.01124 (16)	0.00003 (14)	0.00135 (12)	0.00022 (13)
Br1	0.0145 (2)	0.0135 (2)	0.0149 (2)	0.00045 (19)	0.00676 (19)	0.00145 (19)
Br2	0.0203 (2)	0.0149 (2)	0.0113 (2)	−0.0055 (2)	0.00477 (19)	−0.00073 (19)
O1	0.0152 (17)	0.031 (2)	0.0085 (17)	0.0037 (16)	0.0025 (14)	0.0009 (15)
N1	0.0140 (19)	0.024 (2)	0.0074 (19)	0.0003 (18)	0.0071 (16)	−0.0001 (19)
C2	0.012 (2)	0.016 (2)	0.014 (2)	0.001 (2)	0.0053 (18)	−0.001 (2)
N3	0.0101 (18)	0.0153 (19)	0.011 (2)	0.0016 (17)	0.0014 (15)	0.0012 (17)
C4	0.011 (2)	0.013 (2)	0.014 (2)	−0.0006 (19)	0.0013 (18)	0.002 (2)
C4A	0.010 (2)	0.013 (2)	0.011 (2)	0.0027 (18)	0.0011 (18)	0.003 (2)
C5	0.013 (2)	0.028 (3)	0.012 (2)	−0.001 (2)	0.003 (2)	0.003 (2)
C6	0.010 (2)	0.028 (3)	0.021 (3)	−0.002 (2)	0.0029 (19)	0.005 (2)
C7	0.016 (2)	0.030 (3)	0.012 (2)	−0.002 (2)	−0.0035 (19)	0.004 (2)
C8	0.019 (3)	0.027 (3)	0.009 (2)	−0.002 (2)	0.0016 (19)	0.002 (2)
C8A	0.012 (2)	0.015 (2)	0.010 (2)	−0.0025 (19)	0.0021 (18)	0.004 (2)

Geometric parameters (Å, º) top

Cd1—N3	2.238 (4)	C4—C4A	1.460 (6)
Cd1—Br2ⁱ	2.5886 (6)	C4A—C8A	1.394 (6)
Cd1—Br1	2.6494 (6)	C4A—C5	1.396 (6)
Cd1—Br1ⁱⁱ	2.7302 (6)	C5—C6	1.371 (7)
Cd1—Br2	2.8574 (6)	C5—H5	0.9500
O1—C4	1.236 (5)	C6—C7	1.395 (7)
N1—C2	1.317 (6)	C6—H6	0.9500
N1—C8A	1.386 (6)	C7—C8	1.378 (7)
N1—H1	0.88 (2)	C7—H7	0.9500
C2—N3	1.321 (6)	C8—C8A	1.403 (7)
C2—H2	0.9500	C8—H8	0.9500
N3—C4	1.388 (6)

N3—Cd1—Br2ⁱ	126.23 (10)	O1—C4—N3	119.2 (4)
N3—Cd1—Br1	114.78 (10)	O1—C4—C4A	123.7 (4)
Br2ⁱ—Cd1—Br1	117.82 (2)	N3—C4—C4A	117.1 (4)
N3—Cd1—Br1ⁱⁱ	98.72 (11)	C8A—C4A—C5	118.7 (4)
Br2ⁱ—Cd1—Br1ⁱⁱ	93.35 (2)	C8A—C4A—C4	119.0 (4)
Br1—Cd1—Br1ⁱⁱ	88.152 (19)	C5—C4A—C4	122.3 (4)
N3—Cd1—Br2	84.61 (11)	C6—C5—C4A	120.6 (5)
Br2ⁱ—Cd1—Br2	88.56 (2)	C6—C5—H5	119.7
Br1—Cd1—Br2	85.999 (18)	C4A—C5—H5	119.7
Br1ⁱⁱ—Cd1—Br2	174.08 (2)	C5—C6—C7	120.4 (5)
Cd1—Br1—Cd1ⁱⁱ	91.846 (19)	C5—C6—H6	119.8
Cd1ⁱ—Br2—Cd1	91.44 (2)	C7—C6—H6	119.8
C2—N1—C8A	120.8 (4)	C8—C7—C6	120.5 (5)
C2—N1—H1	116 (4)	C8—C7—H7	119.8
C8A—N1—H1	124 (4)	C6—C7—H7	119.8
N1—C2—N3	124.1 (4)	C7—C8—C8A	118.9 (5)
N1—C2—H2	118.0	C7—C8—H8	120.6
N3—C2—H2	118.0	C8A—C8—H8	120.6
C2—N3—C4	120.4 (4)	N1—C8A—C4A	118.5 (4)
C2—N3—Cd1	121.4 (3)	N1—C8A—C8	120.4 (4)
C4—N3—Cd1	118.2 (3)	C4A—C8A—C8	121.0 (4)

C8A—N1—C2—N3	−0.1 (8)	C4—C4A—C5—C6	179.2 (5)
N1—C2—N3—C4	1.8 (8)	C4A—C5—C6—C7	0.5 (8)
N1—C2—N3—Cd1	−177.8 (4)	C5—C6—C7—C8	0.7 (9)
C2—N3—C4—O1	177.7 (5)	C6—C7—C8—C8A	−1.3 (8)
Cd1—N3—C4—O1	−2.7 (6)	C2—N1—C8A—C4A	−1.3 (7)
C2—N3—C4—C4A	−2.0 (7)	C2—N1—C8A—C8	179.5 (5)
Cd1—N3—C4—C4A	177.7 (3)	C5—C4A—C8A—N1	−178.7 (5)
O1—C4—C4A—C8A	−179.1 (5)	C4—C4A—C8A—N1	1.1 (7)
N3—C4—C4A—C8A	0.6 (7)	C5—C4A—C8A—C8	0.4 (8)
O1—C4—C4A—C5	0.7 (8)	C4—C4A—C8A—C8	−179.8 (5)
N3—C4—C4A—C5	−179.7 (5)	C7—C8—C8A—N1	179.9 (5)
C8A—C4A—C5—C6	−1.0 (8)	C7—C8—C8A—C4A	0.8 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱⁱ	0.87 (3)	2.10 (3)	2.917 (6)	155 (6)

Symmetry code: (iii) x, −y+3/2, z+1/2.

catena-Poly[[[quinazolin-4(3H)-one-κN³]mercury(II)]-di-µ-chlorido] (II) top

Crystal data top

[HgCl₂(C₈H₆N₂O)]	Z = 2
M_r = 417.64	F(000) = 380
Triclinic, P1	D_x = 2.791 Mg m⁻³
a = 6.8191 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0735 (8) Å	Cell parameters from 3121 reflections
c = 10.4659 (12) Å	θ = 3.0–29.9°
α = 85.718 (2)°	µ = 15.99 mm⁻¹
β = 80.7887 (19)°	T = 100 K
γ = 89.152 (2)°	Prism, colourless
V = 496.92 (10) Å³	0.04 × 0.03 × 0.03 mm

Data collection top

Bruker D8 gonimeter with APEX CCD detector diffractometer	5037 independent reflections
Radiation source: Incoatec microsource	4693 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.050
ω scans	θ_max = 30.3°, θ_min = 2.9°
Absorption correction: multi-scan (TWINABS; Bruker, 2014)	h = −9→9
T_min = 0.302, T_max = 0.433	k = −9→10
14434 measured reflections	l = 0→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.020P)² + 2.5P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5037 reflections	Δρ_max = 1.54 e Å⁻³
132 parameters	Δρ_min = −1.49 e Å⁻³
1 restraint

Special details top

Refinement. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
Hg1	0.96071 (4)	0.24641 (4)	0.07042 (3)	0.01548 (9)
Cl2	1.2589 (3)	0.0702 (3)	0.01773 (19)	0.0173 (4)
Cl1	0.8430 (3)	0.4314 (2)	−0.1209 (2)	0.0188 (4)
O1	0.9528 (7)	0.2176 (8)	0.3605 (5)	0.0212 (11)
N1	0.3826 (9)	0.2857 (9)	0.3209 (6)	0.0138 (12)
H1	0.255 (5)	0.293 (12)	0.313 (8)	0.03 (2)*
C2	0.5279 (11)	0.2835 (10)	0.2211 (7)	0.0161 (15)
H2	0.494018	0.298894	0.136314	0.019*
N3	0.7156 (9)	0.2615 (8)	0.2317 (6)	0.0129 (12)
C4	0.7779 (10)	0.2372 (10)	0.3539 (7)	0.0113 (13)
C4A	0.6195 (11)	0.2370 (10)	0.4663 (7)	0.0134 (14)
C5	0.6608 (11)	0.2103 (11)	0.5938 (7)	0.0161 (15)
H5	0.793612	0.189228	0.608450	0.019*
C6	0.5093 (12)	0.2146 (11)	0.6969 (8)	0.0203 (16)
H6	0.537995	0.197419	0.782925	0.024*
C7	0.3144 (12)	0.2440 (11)	0.6770 (8)	0.0202 (16)
H7	0.211185	0.246517	0.749509	0.024*
C8	0.2688 (11)	0.2694 (11)	0.5539 (7)	0.0193 (16)
H8	0.135319	0.290262	0.540841	0.023*
C8A	0.4223 (10)	0.2640 (10)	0.4475 (7)	0.0130 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.01190 (13)	0.02113 (15)	0.01333 (14)	0.00139 (11)	−0.00131 (9)	−0.00250 (11)
Cl2	0.0123 (9)	0.0204 (9)	0.0201 (10)	0.0022 (7)	−0.0039 (7)	−0.0058 (7)
Cl1	0.0219 (10)	0.0179 (8)	0.0194 (10)	−0.0013 (7)	−0.0120 (8)	−0.0003 (7)
O1	0.013 (3)	0.034 (3)	0.015 (3)	0.002 (2)	−0.003 (2)	0.002 (3)
N1	0.007 (3)	0.022 (3)	0.013 (3)	−0.001 (2)	−0.005 (2)	0.001 (2)
C2	0.014 (4)	0.019 (4)	0.015 (4)	0.001 (3)	−0.002 (3)	−0.003 (3)
N3	0.014 (3)	0.015 (3)	0.011 (3)	0.003 (2)	−0.003 (2)	−0.003 (2)
C4	0.013 (3)	0.013 (3)	0.008 (3)	−0.001 (3)	−0.003 (3)	−0.001 (3)
C4A	0.014 (3)	0.014 (3)	0.012 (3)	−0.002 (3)	−0.001 (3)	−0.001 (3)
C5	0.013 (3)	0.023 (4)	0.013 (4)	−0.004 (3)	−0.004 (3)	0.001 (3)
C6	0.023 (4)	0.025 (4)	0.012 (4)	−0.004 (3)	−0.002 (3)	−0.001 (3)
C7	0.018 (4)	0.025 (4)	0.016 (4)	0.000 (3)	0.002 (3)	−0.003 (3)
C8	0.014 (4)	0.028 (4)	0.016 (4)	0.000 (3)	−0.003 (3)	0.000 (3)
C8A	0.010 (3)	0.015 (3)	0.014 (3)	0.000 (3)	−0.002 (3)	0.000 (3)

Geometric parameters (Å, º) top

Hg1—N3	2.185 (6)	C4—C4A	1.464 (10)
Hg1—Cl2	2.3791 (18)	C4A—C8A	1.398 (10)
Hg1—Cl1	2.5416 (19)	C4A—C5	1.406 (10)
Hg1—Cl1ⁱ	2.7861 (18)	C5—C6	1.372 (10)
O1—C4	1.211 (8)	C5—H5	0.9500
N1—C2	1.320 (9)	C6—C7	1.389 (11)
N1—C8A	1.392 (9)	C6—H6	0.9500
N1—H1	0.89 (3)	C7—C8	1.371 (10)
C2—N3	1.309 (9)	C7—H7	0.9500
C2—H2	0.9500	C8—C8A	1.403 (10)
N3—C4	1.409 (9)	C8—H8	0.9500

N3—Hg1—Cl2	138.49 (16)	C8A—C4A—C5	118.8 (7)
N3—Hg1—Cl1	105.30 (16)	C8A—C4A—C4	119.7 (7)
Cl2—Hg1—Cl1	114.98 (7)	C5—C4A—C4	121.4 (7)
N3—Hg1—Cl1ⁱ	96.08 (16)	C6—C5—C4A	119.9 (7)
Cl2—Hg1—Cl1ⁱ	93.94 (6)	C6—C5—H5	120.0
Cl1—Hg1—Cl1ⁱ	89.50 (6)	C4A—C5—H5	120.0
Hg1—Cl1—Hg1ⁱ	90.50 (6)	C5—C6—C7	120.7 (7)
C2—N1—C8A	120.8 (6)	C5—C6—H6	119.7
C2—N1—H1	123 (6)	C7—C6—H6	119.7
C8A—N1—H1	116 (6)	C8—C7—C6	120.9 (7)
N3—C2—N1	124.0 (7)	C8—C7—H7	119.6
N3—C2—H2	118.0	C6—C7—H7	119.6
N1—C2—H2	118.0	C7—C8—C8A	119.0 (7)
C2—N3—C4	121.5 (6)	C7—C8—H8	120.5
C2—N3—Hg1	125.6 (5)	C8A—C8—H8	120.5
C4—N3—Hg1	112.9 (4)	N1—C8A—C4A	118.3 (6)
O1—C4—N3	119.9 (6)	N1—C8A—C8	121.0 (7)
O1—C4—C4A	124.5 (6)	C4A—C8A—C8	120.6 (7)
N3—C4—C4A	115.6 (6)

C8A—N1—C2—N3	0.0 (11)	C4—C4A—C5—C6	178.7 (7)
N1—C2—N3—C4	0.2 (11)	C4A—C5—C6—C7	0.4 (12)
N1—C2—N3—Hg1	177.6 (5)	C5—C6—C7—C8	0.0 (12)
C2—N3—C4—O1	−179.8 (7)	C6—C7—C8—C8A	0.4 (12)
Hg1—N3—C4—O1	2.4 (8)	C2—N1—C8A—C4A	−1.0 (10)
C2—N3—C4—C4A	0.5 (10)	C2—N1—C8A—C8	178.9 (7)
Hg1—N3—C4—C4A	−177.3 (5)	C5—C4A—C8A—N1	−178.5 (6)
O1—C4—C4A—C8A	178.9 (7)	C4—C4A—C8A—N1	1.6 (10)
N3—C4—C4A—C8A	−1.4 (9)	C5—C4A—C8A—C8	1.6 (10)
O1—C4—C4A—C5	−1.0 (11)	C4—C4A—C8A—C8	−178.3 (7)
N3—C4—C4A—C5	178.7 (6)	C7—C8—C8A—N1	178.8 (7)
C8A—C4A—C5—C6	−1.2 (11)	C7—C8—C8A—C4A	−1.2 (11)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱⁱ	0.89 (4)	2.11 (4)	2.935 (8)	155 (7)

Symmetry code: (ii) x−1, y, z.

Diiodidobis[quinazolin-4(3H)-one-κN³]cadmium(II) (III) top

Crystal data top

[CdI₂(C₁₆H₁₂N₄O₂)]	F(000) = 1224
M_r = 658.50	D_x = 2.453 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.242 (3) Å	Cell parameters from 7294 reflections
b = 6.8450 (9) Å	θ = 3.1–30.6°
c = 13.3702 (17) Å	µ = 4.70 mm⁻¹
β = 118.8220 (16)°	T = 100 K
V = 1783.4 (4) Å³	Plate, colourless
Z = 4	0.12 × 0.10 × 0.04 mm

Data collection top

Bruker D8 gonimeter with APEX CCD detector diffractometer	2687 independent reflections
Radiation source: Incoatec microsource	2519 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.024
ω scans	θ_max = 30.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −31→31
T_min = 0.544, T_max = 0.746	k = −9→9
13210 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0331P)² + 1.7P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
2687 reflections	Δρ_max = 3.17 e Å⁻³
119 parameters	Δρ_min = −0.49 e Å⁻³
2 restraints

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	−0.02284 (2)	0.27011 (3)	0.06205 (2)	0.01738 (7)
Cd1	0.000000	0.06009 (4)	0.250000	0.01209 (8)	0.9682 (8)
Cd2	0.000000	−0.5534 (10)	0.250000	0.01209 (8)	0.0318 (8)
O1	−0.15047 (11)	0.1341 (3)	0.16751 (18)	0.0192 (4)
N1	−0.14386 (12)	−0.4477 (3)	0.2024 (2)	0.0156 (5)
H1A	−0.1400 (18)	−0.583 (5)	0.200 (3)	0.019*
C2	−0.08880 (14)	−0.3397 (4)	0.2268 (2)	0.0163 (5)
H2A	−0.046045	−0.405307	0.254856	0.020*
N3	−0.08910 (11)	−0.1482 (3)	0.21497 (19)	0.0135 (4)
C4	−0.15069 (13)	−0.0452 (4)	0.1747 (2)	0.0117 (5)
C4A	−0.21284 (13)	−0.1587 (4)	0.1429 (2)	0.0120 (5)
C5	−0.27777 (14)	−0.0702 (4)	0.0976 (2)	0.0161 (5)
H5A	−0.282158	0.066631	0.083981	0.019*
C6	−0.33542 (15)	−0.1813 (5)	0.0726 (2)	0.0188 (6)
H6A	−0.379070	−0.120238	0.042601	0.023*
C7	−0.32946 (15)	−0.3836 (5)	0.0915 (2)	0.0191 (6)
H7A	−0.369040	−0.458717	0.075289	0.023*
C8	−0.26645 (15)	−0.4744 (4)	0.1334 (2)	0.0172 (5)
H8A	−0.262633	−0.611862	0.144689	0.021*
C8A	−0.20823 (13)	−0.3616 (4)	0.1592 (2)	0.0131 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01805 (11)	0.01668 (11)	0.01536 (10)	−0.00240 (6)	0.00642 (8)	0.00158 (6)
Cd1	0.01073 (13)	0.00997 (13)	0.01466 (14)	0.000	0.00539 (11)	0.000
Cd2	0.01073 (13)	0.00997 (13)	0.01466 (14)	0.000	0.00539 (11)	0.000
O1	0.0209 (10)	0.0124 (10)	0.0246 (11)	−0.0019 (8)	0.0112 (9)	−0.0008 (8)
N1	0.0173 (11)	0.0099 (11)	0.0214 (12)	0.0013 (8)	0.0108 (10)	0.0023 (9)
C2	0.0129 (12)	0.0168 (13)	0.0194 (13)	0.0036 (10)	0.0080 (11)	0.0029 (11)
N3	0.0115 (10)	0.0147 (11)	0.0142 (10)	−0.0005 (8)	0.0060 (9)	0.0006 (9)
C4	0.0151 (12)	0.0102 (12)	0.0105 (11)	−0.0007 (9)	0.0067 (10)	−0.0012 (9)
C4A	0.0134 (12)	0.0124 (12)	0.0105 (11)	0.0001 (9)	0.0059 (10)	−0.0011 (9)
C5	0.0166 (12)	0.0156 (13)	0.0154 (13)	0.0020 (10)	0.0072 (11)	0.0001 (10)
C6	0.0124 (12)	0.0289 (16)	0.0140 (13)	0.0016 (11)	0.0055 (10)	−0.0019 (11)
C7	0.0165 (13)	0.0259 (15)	0.0159 (13)	−0.0066 (11)	0.0087 (11)	−0.0028 (11)
C8	0.0212 (14)	0.0156 (13)	0.0167 (13)	−0.0050 (11)	0.0108 (11)	−0.0026 (10)
C8A	0.0146 (12)	0.0136 (13)	0.0111 (11)	−0.0009 (10)	0.0061 (10)	−0.0005 (9)

Geometric parameters (Å, º) top

I1—Cd2ⁱ	2.608 (3)	N3—C4	1.397 (3)
I1—Cd1	2.7219 (4)	C4—C4A	1.459 (4)
Cd1—N3ⁱⁱ	2.299 (2)	C4A—C8A	1.402 (4)
Cd1—N3	2.299 (2)	C4A—C5	1.406 (4)
Cd2—C2ⁱⁱ	2.355 (5)	C5—C6	1.386 (4)
Cd2—C2	2.355 (5)	C5—H5A	0.9500
O1—C4	1.232 (3)	C6—C7	1.403 (5)
N1—C2	1.329 (4)	C6—H6A	0.9500
N1—C8A	1.391 (4)	C7—C8	1.381 (4)
N1—H1A	0.93 (4)	C7—H7A	0.9500
C2—N3	1.320 (4)	C8—C8A	1.401 (4)
C2—H2A	0.9500	C8—H8A	0.9500

N3ⁱⁱ—Cd1—N3	103.32 (12)	C2—N3—Cd1	129.61 (17)
N3ⁱⁱ—Cd1—I1	105.94 (6)	C4—N3—Cd1	110.74 (17)
N3—Cd1—I1	112.37 (6)	O1—C4—N3	119.5 (2)
N3ⁱⁱ—Cd1—I1ⁱⁱ	112.37 (6)	O1—C4—C4A	123.2 (2)
N3—Cd1—I1ⁱⁱ	105.94 (6)	N3—C4—C4A	117.3 (2)
I1—Cd1—I1ⁱⁱ	116.237 (16)	C8A—C4A—C5	118.5 (2)
C2ⁱⁱ—Cd2—C2	103.2 (3)	C8A—C4A—C4	119.6 (2)
C2ⁱⁱ—Cd2—I1ⁱⁱⁱ	100.14 (7)	C5—C4A—C4	121.9 (2)
C2—Cd2—I1ⁱⁱⁱ	113.53 (8)	C6—C5—C4A	120.4 (3)
C2ⁱⁱ—Cd2—I1^iv	113.53 (8)	C6—C5—H5A	119.8
C2—Cd2—I1^iv	100.14 (7)	C4A—C5—H5A	119.8
I1ⁱⁱⁱ—Cd2—I1^iv	124.8 (3)	C5—C6—C7	120.1 (3)
C2—Cd2—H2Aⁱⁱ	97.1 (4)	C5—C6—H6A	119.9
I1ⁱⁱⁱ—Cd2—H2Aⁱⁱ	95.37 (11)	C7—C6—H6A	119.9
I1^iv—Cd2—H2Aⁱⁱ	123.21 (12)	C8—C7—C6	120.5 (3)
C2—N1—C8A	120.6 (2)	C8—C7—H7A	119.8
C2—N1—H1A	118 (2)	C6—C7—H7A	119.8
C8A—N1—H1A	120 (2)	C7—C8—C8A	119.2 (3)
N3—C2—N1	124.9 (2)	C7—C8—H8A	120.4
N3—C2—Cd2	126.0 (2)	C8A—C8—H8A	120.4
N1—C2—Cd2	107.6 (2)	N1—C8A—C8	120.9 (3)
N3—C2—H2A	117.6	N1—C8A—C4A	117.9 (2)
N1—C2—H2A	117.6	C8—C8A—C4A	121.2 (2)
C2—N3—C4	119.6 (2)

C8A—N1—C2—N3	1.1 (4)	C8A—C4A—C5—C6	1.7 (4)
C8A—N1—C2—Cd2	−165.5 (2)	C4—C4A—C5—C6	−177.4 (3)
N1—C2—N3—C4	0.4 (4)	C4A—C5—C6—C7	−0.6 (4)
Cd2—C2—N3—C4	164.55 (19)	C5—C6—C7—C8	−1.0 (4)
N1—C2—N3—Cd1	−179.0 (2)	C6—C7—C8—C8A	1.3 (4)
C2—N3—C4—O1	177.5 (2)	C2—N1—C8A—C8	−179.9 (3)
Cd1—N3—C4—O1	−3.0 (3)	C2—N1—C8A—C4A	−0.2 (4)
C2—N3—C4—C4A	−2.6 (4)	C7—C8—C8A—N1	179.5 (3)
Cd1—N3—C4—C4A	176.94 (17)	C7—C8—C8A—C4A	−0.1 (4)
O1—C4—C4A—C8A	−176.8 (2)	C5—C4A—C8A—N1	179.0 (2)
N3—C4—C4A—C8A	3.3 (3)	C4—C4A—C8A—N1	−1.9 (4)
O1—C4—C4A—C5	2.3 (4)	C5—C4A—C8A—C8	−1.4 (4)
N3—C4—C4A—C5	−177.6 (2)	C4—C4A—C8A—C8	177.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱⁱⁱ	0.93 (3)	1.97 (3)	2.893 (3)	168 (4)

Symmetry code: (iii) x, y−1, z.

Acknowledgements

We gratefully acknowledge the scholarship of the German Academic Exchange Service (DAAD). The help of all members of the Institute of Inorganic Chemistry, RWTH Aachen University is greatly appreciated.

Funding information

Funding for this research was provided by: Deutscher Akademischer Austauschdienst.

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