research communications
Metal halide coordination compounds with quinazolin-4(3H)-one
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
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 CdII atom in (I) has an almost trigonal–bipyramidal coordination environment, whereas the HgII 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 CdII 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 CdII position for this alternative orientation was taken into account during 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.
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 via the nitrogen atom ortho to the quinazolinone carbonyl group (mode 2) have been observed (Fig. 1). An AgI coordination compound (Li et al., 2015) provides an example for the co-existence of both binding modes in the same 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 CdII 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).
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 I) consists of a CdII cation, two Br− ligands and one quinoz ligand attached in mode 2 (Fig. 2). The cation adopts a 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 D3h to C4v. 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 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 CdII 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 CdII with two iodido and two additional ligands have been documented, and (III) falls into this category. The 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 C2/c, 4e. Its coordination environment is characterized by a τ4 descriptor (Yang et al., 2007) of 0.93, corresponding to an almost undistorted tetrahedron.
of (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).
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 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 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 were obtained.
5. Refinement
Crystal data, data collection and structure . 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.
details are summarized in Table 4Several 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 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 and not of the individual crystal chosen for the data collection.
Supporting information
https://doi.org/10.1107/S2056989023004802/wm5681sup1.cif
contains datablocks I, II, III, GLOBAL. DOI: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
For all structures, data collection: APEX2 (Bruker, 2014); cell
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).[CdBr2(C8H6N2O)] | F(000) = 776 |
Mr = 418.37 | Dx = 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 |
Bruker D8 gonimeter with APEX CCD detector diffractometer | 5868 independent reflections |
Radiation source: Incoatec microsource | 4717 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.089 |
ω scans | θmax = 30.7°, θmin = 3.0° |
Absorption correction: multi-scan (TWINABS; Bruker, 2014) | h = −15→14 |
Tmin = 0.446, Tmax = 0.746 | k = 0→10 |
65521 measured reflections | l = 0→19 |
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(Fo2) + (0.026P)2 + 1.8P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
5868 reflections | Δρmax = 1.13 e Å−3 |
132 parameters | Δρmin = −0.96 e Å−3 |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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. |
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. |
[HgCl2(C8H6N2O)] | Z = 2 |
Mr = 417.64 | F(000) = 380 |
Triclinic, P1 | Dx = 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 |
Bruker D8 gonimeter with APEX CCD detector diffractometer | 5037 independent reflections |
Radiation source: Incoatec microsource | 4693 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.050 |
ω scans | θmax = 30.3°, θmin = 2.9° |
Absorption correction: multi-scan (TWINABS; Bruker, 2014) | h = −9→9 |
Tmin = 0.302, Tmax = 0.433 | k = −9→10 |
14434 measured reflections | l = 0→14 |
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(Fo2) + (0.020P)2 + 2.5P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5037 reflections | Δρmax = 1.54 e Å−3 |
132 parameters | Δρmin = −1.49 e Å−3 |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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. |
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. |
[CdI2(C16H12N4O2)] | F(000) = 1224 |
Mr = 658.50 | Dx = 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 |
Bruker D8 gonimeter with APEX CCD detector diffractometer | 2687 independent reflections |
Radiation source: Incoatec microsource | 2519 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.024 |
ω scans | θmax = 30.7°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −31→31 |
Tmin = 0.544, Tmax = 0.746 | k = −9→9 |
13210 measured reflections | l = −18→18 |
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(Fo2) + (0.0331P)2 + 1.7P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
2687 reflections | Δρmax = 3.17 e Å−3 |
119 parameters | Δρmin = −0.49 e Å−3 |
2 restraints |
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. |
x | y | z | Uiso*/Ueq | 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) |
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) |
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—I1iv | 113.53 (8) | C6—C5—H5A | 119.8 |
C2—Cd2—I1iv | 100.14 (7) | C4A—C5—H5A | 119.8 |
I1iii—Cd2—I1iv | 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 |
I1iv—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. |
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.
References
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Bruker (2014). APEX2, SAINT, SADABS and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Đaković, M., Soldin, Ž., Kukovec, B.-M., Kodrin, I., Aakeröy, C. B., Baus, N. & Rinkovec, T. (2018). IUCrJ, 5, 13–21. Web of Science CSD CrossRef PubMed IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Holmes, R. R. (1984). Prog. Inorg. Chem. 32, 119–235. CrossRef CAS Web of Science Google Scholar
Hu, C. & Englert, U. (2001). CrystEngComm, 3, 91–95. Web of Science CSD CrossRef Google Scholar
Hu, C. & Englert, U. (2002). CrystEngComm, 4, 20–25. Web of Science CSD CrossRef Google Scholar
Hu, C., Kalf, I. & Englert, U. (2007). CrystEngComm, 9, 603–610. Web of Science CSD CrossRef CAS Google Scholar
Hu, C., Li, Q. & Englert, U. (2003). CrystEngComm, 5, 519–529. Web of Science CSD CrossRef CAS Google Scholar
Li, S. X., Liao, B. L., Luo, P. & Jiang, Y. M. (2015). Chin. J. Inorg. Chem. 31, 291–296. CAS Google Scholar
Merkens, C., Kalf, I. & Englert, U. (2010). Z. Anorg. Allg. Chem. 636, 681–684. Web of Science CSD CrossRef CAS Google Scholar
Merkens, C., Truong, K.-N. & Englert, U. (2014). Acta Cryst. B70, 705–713. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shomurotova, S., Turgunov, K. K., Mukhamedov, N. & Tashkhodjaev, B. (2012). Acta Cryst. E68, m724. CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Terwingen, S. van, Nachtigall, N., Ebel, B. & Englert, U. (2021). Cryst. Growth Des. 21, 2962–2969. Google Scholar
Truong, K.-N., Merkens, C. & Englert, U. (2017). Acta Cryst. B73, 981–991. Web of Science CSD CrossRef IUCr Journals Google Scholar
Turgunov, K. & Englert, U. (2010). Acta Cryst. E66, m1457. Web of Science CSD CrossRef IUCr Journals Google Scholar
Turgunov, K., Shomurotova, S., Mukhamedov, N. & Tashkhodjaev, B. (2010). Acta Cryst. E66, m1680. Web of Science CSD CrossRef IUCr Journals Google Scholar
Turgunov, K. K., Wang, Y., Englert, U. & Shakhidoyatov, K. M. (2011). Acta Cryst. E67, m953–m954. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955–964. Web of Science CSD CrossRef PubMed CAS Google Scholar
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