research communications
μ-chlorido-bis[dichloridomercurate(II)]
Hirshfeld surface analysis and physicochemical characterization of bis[4-(dimethylamino)pyridinium] di-aUniversity of Tunis El Manar, Faculty of Sciences of Tunis, Laboratory of Materials, Crystal Chemistry and Applied Thermodynamics, 2092 El Manar II, Tunis, Tunisia, and bChemistry Department, College of Science, IMSIU (Imam Mohammad Ibn Saud Islamic University), Riyadh 11623, Kingdom of Saudi Arabia
*Correspondence e-mail: chebhamouda@yahoo.fr
The title molecular salt, (C7H11N2)2[Hg2Cl6], crystallizes with two 4-(dimethylamino)pyridinium cations (A and B) and two half hexachloridodimercurate(II) anions in the The organic cations exhibit essentially the same features with an almost planar pyridyl ring (r.m.s. deviations of 0.0028 and 0.0109 Å), which forms an inclined dihedral angle with the dimethyamino group [3.06 (1) and 1.61 (1)°, respectively]. The dimethylamino groups in the two cations are planar, and the C—N bond lengths are shorter than that in 4-(dimethylamino)pyridine. In the crystal, mixed cation–anion layers lying parallel to the (010) plane are formed through N—H⋯Cl hydrogen bonds and adjacent layers are linked by C—H⋯Cl hydrogen bonds, forming a three-dimensional network. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above intermolecular interactions, but also serve to further differentiate the weaker intermolecular interactions formed by the organic cations and inorganic anions, such as π–π and Cl⋯Cl interactions. The powder XRD data confirms the phase purity of the crystalline sample. Furthermore, the vibrational absorption bands were identified by IR spectroscopy and the optical properties were studied by using optical UV–visible absorption spectroscopy.
Keywords: crystal structure; chloromercurate(II) salt; 4-dimethylaminopyridium; Hirshfeld surface; fingerprint plots; hybrid compound.
CCDC reference: 1911692
1. Chemical context
Hybrid organic–inorganic materials have been widely studied in recent years for their promising applications in different fields, including catalysis, magnetism and optics and for their luminescence properties (Clément et al., 1994; Rabu et al., 2001; Hu et al., 2003; Morris et al., 2008). However, owing to the confinement of the inorganic layers, the organic cations have to possess the right ionic bond and as well as hydrogen bonds, to fit the coordination environment provided by the inorganic framework for stabilization of these organic–inorganic hybrid systems.
Hybrids based on mercury have been synthesized and characterized with simple, different techniques, thanks to their self-assembling character (Mitzi et al., 2001) and are very interesting both for fundamental physics exploration such as electronic confinement (Wei et al., 2015) or as low-dimensional magnetic systems (Fersi et al., 2015) and diversify the field of technological applications.
A number of chloromercurate(II) complexes have been shown to exhibit ferroelectric behaviour (Mitsui & Nakamura, 1990) and interest has focused on the mechanism of the ferroelectric–paraelectric (White, 1963; Körfer et al., 1988; Jiang et al., 1995; Liesegang et al., 1995) for which structural information is crucial. In addition, the ability of the anions in this class of compounds to exhibit a wide range of geometry, stoichiometry and connectivity has long been known (Grdenic, 1965). This flexibility is a result of the large volume and spherical charge distribution of the Hg2+ ion, which are a consequence of the filled 4f and 5d electron shells. Moreover, organic–inorganic materials with pyridine and its derivatives as template agents have led to the preparation of some materials with interesting physical properties (Aakeröy et al., 2000; Prince et al., 2003) and biological activities (Bossert et al., 1981; Wang et al., 1989).
As part of our continuing investigation of new hybrid compounds containing an organic cation and an inorganic anion such as CrO42− (Chebbi et al., 2000; Chebbi & Driss, 2001, 2002a,b, 2004), Cr2O72− (Chebbi et al., 2016, Ben Smail et al., 2017), NO3− (Chebbi et al., 2014, 2018) and ClO4− (Chebbi et al., 2017; Ben Jomaa et al., 2018), we report in this work the the Hirshfeld surface analysis and the physicochemical characterization of a new organic chloromercurate(II), (C7H11N2)2[Hg2Cl6] (I).
2. Structural commentary
The A and B), and two half [Hg2Cl6]2− anions (Fig. 1). The two independent [Hg2(1,2)Cl6]2− anions are found to adopt a centrosymmetric arrangement with terminal Cl1—Hg1—Cl3 and Cl4—Hg2—Cl5 angles of 141.4 (1)° and 141.7 (1)° respectively. Each anion appears to be a distorted edge-shared bitetrahedron, similar to that reported by Larock et al. (1987), with its center of mass coincident with a crystallographic center of symmetry. The two independent Hg⋯Cl bridging distances are 2.539 (2) and 2.542 (2) Å, leading to a slightly asymmetric bridging system as has been found in most structures containing the [Hg2Cl6]2− moiety (Linden et al., 1999; Zabel et al., 2008). In each anion, the two terminal Hg—Cl bonds are quite short [Hg1—Cl1 = 2.371 (2) and Hg1—Cl3 = 2.380 (2) Å, Hg2—Cl4 = 2.367 (3) and Hg2—Cl5 = 2.392 (2) Å] with a Cl1—Hg1—Cl2 and Cl4—Hg2—Cl6 angles of 112.01 (9) and 112.72 (10)°, respectively. Assessment of the organic geometrical features shows that they exhibit essentially the same features with an almost planar pyridyl ring (r.m.s. deviation = 0.0028 and 0.0109 Å for C1A–C5A/N1A and C1B–C5B/N1B, respectively), which forms an inclined dihedral angle with the dimethyamino group [3.06 (1) and 1.61 (1)°, respectively]. The dimethylamino groups in the two cations are planar and the C—N bond lengths [1.357 (11) Å for A and 1.326 (11) Å for B] are shorter than that in 4-dimethylaminopyridine [1.367 (2) Å; Ohms & Guth, 1984]. These findings indicate the presence of strong conjugation between the dimethylamino group and the pyridine ring. The C3A—N1A—C4A [121.2 (8)°] and C3B—N1B—C4B [119.8 (9)°] bond angles are wider than that in pyridine (116.94°; Sørensen et al., 1974), which indicates that the pyridine ring N atom is protonated. Examination of the C—C(N) distances and C—C—C (N), C—N—C angles in the 4-(dimethylamino)pyridinium dications (A and B) shows no significant difference from those obtained in other organic materials associated with the same organic groups (Chao et al., 1977; Mustaqim et al., 2005).
of the title compound comprises two 4-(dimethylamino)pyridinium cations (The experimental powder X-ray diffraction pattern of the title compound, (C7H11N2)2[Hg2Cl6] is in good agreement with that simulated (Fig. 2). This indicates the purity of the synthesized product and confirms the crystal data used.
3. Supramolecular features
In the , Fig. 3). A mixed layer is formed by alternating of organic and inorganic columns parallel to the [100] direction (Fig. 4). The cations (A or B) interact via offset face-to-face π–π stacking interactions, leading to two types of organic columns formed by the cations (A or B) with centroid-centroid distances of 3.698 (2) and 3.982 (2) Å, respectively (Fig. 5) (Janiak, 2000; Ben Moussa et al., 2018). Similarly, the hexachloridodimercurate(II) anions are dispersed parallel to the a axis whose cohesion is ensured by Cl⋯Cl [3.652 (6) Å] and Hg⋯Cl [3.167 (7) Å] weak interactions (Sumanesh et al., 2016; Ben Moussa et al., 2019a,b; Fig. 6).
mixed cation–anion layers lying parallel to the (010) plane are formed through N—H⋯Cl hydrogen bonds and adjacent layers are linked by C—H⋯Cl hydrogen bonds, forming a three-dimensional network (Table 14. Vibrational study
The obtained FT–IR spectrum for the studied hexachloridodimercurate(II) salt is depicted in Fig. 7. Detailed assignment of all bands observed in the infrared spectrum of the 4-(dimethylamino)pyridinium cation in the title compound is based on the comparison with other compounds associated to the same cation (Koleva et al., 2008; Hu et al., 2012). In the region of high frequencies, the bands at 3243, 3130, 3100, 2959 cm−1 are due to the stretching vibrations of the N—H and C—H bonds. The band at 1646 cm−1 is assigned to the N—H bending mode. The bands at 1557 and 1445 cm−1 are attributed to the C=C and C=N stretching modes of the pyridine ring. The absorption band located at 1212 cm−1 corresponds to the ν(C—N) and ν(C—C) modes. The band at 1056 cm−1 can be attributed to the δ(C—C) mode. The remaining bands in the range 1000 to 500 cm−1 are assigned to γ(C—C), γ(C—H) and γ(C—N) out-of-plane bending modes.
5. Optical properties and frontier molecular orbitals
Optical absorption (OA) measurement of the title compound was performed at ambient temperature in an ethanol solution (10−4 M). As shown in Fig. 8, the OA spectrum exhibits two distinct absorption bands around 213 and 278 nm assigned to the π→π* absorption bands of the 4-(dimethylamino)pyridinium cations. Thus, the experimental band-gap energy obtained from the wavelength is about 3.98 eV. This band-gap value indicates that the grown crystal exhibits semiconductor behavior (Rosencher & Vinter, 2002). The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), known as obtained with a B3LYP/6-311G+(d,p) [H, C, N, Cl]–LANL2DZ [Hg] level calculation are illustrated in Fig. 9. The HOMO is mainly delocalized at the pyridine ring system. After excitation, the charge is localized on the hexachloridodimercurate(II) moieties, as depicted in the LUMO. The calculated HOMO–LUMO energy gap (4.26 eV) is shifted from the experimental value, which may be attributed to solvent effects, compared to the gas-phase calculation.
6. Hirshfeld surface analysis
A Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007) were performed with CrystalExplorer17 (Turner et al., 2017) to investigate the intermolecular interactions in the title compound. Fig. 10a illustrates the Hirshfeld surface mapped over dnorm, which was plotted with a colour scale of −0.211 to 1.132 a.u. with a standard (high) surface resolution. The red spots highlight the interatomic contacts including the N—H⋯Cl and C—H⋯Cl hydrogen bonds.
The shape-index of the Hirshfeld surface is a tool to visualize the π–π stacking by the presence of adjacent red and blue triangles; if there are no adjacent red and/or blue triangles, then there are no π–π interactions. Fig.10b clearly suggests that π–π interactions are present in the title hexachloridodimercurate(II) salt.
Fig. 11a shows the two-dimensional fingerprint of all contacts contributing to the Hirshfeld surface. In Fig. 11b, with two symmetrical wings on the left and right sides illustrate the H⋯Cl/Cl⋯H interactions with a contribution of 49.5%. Fig. 11c illustrates the two-dimensional fingerprint plot of (di, de) points related to H⋯H contacts, which represent a 24.9% contribution. Furthermore, there are Hg⋯Cl/Cl⋯Hg (7.1%; Fig. 11d), C⋯C (3.6%; Fig. 11e) and Cl⋯Cl (1.2%; Fig. 11f) contacts. Fig. 12 shows the percentage contributions of the various contacts in the title structure.
7. Synthesis and crystallization
The title compound was synthesized by dissolving 2 mmol (241 mg) of 4-dimethylaminopyridine 98% (Sigma–Aldrich) in an HCl 36–38% (Sigma–Aldrich) aqueous solution and 1 mmol (273 mg) of mercury(II) chloride HgCl2 (Merck) in ethanol in a molar ratio of 2:1. The mixture was then stirred for 2 h. The resulting aqueous solution was filtered and then evaporated at room temperature, which finally led to the growth of parallelepipedic colourless crystals after one day.
8. Refinement
Crystal data, data collection and structure . H atoms were placed in calculated positions, with N—H = 0.86 Å and C—H = 0.93 or 0.96 Å. Uiso(H) values were constrained to be 1.5Ueq of the for methyl H atoms, and 1.2Ueq for the remaining H atoms. The (111) and (121) reflections were omitted owing to bad disagreement.
details are summarized in Table 2Supporting information
CCDC reference: 1911692
https://doi.org/10.1107/S2056989019013124/vm2222sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019013124/vm2222Isup2.hkl
Data collection: CAD-4 EXPRESS (Duisenberg, 1992; Macíček & Yordanov, 1992); cell
CAD-4 EXPRESS (Duisenberg, 1992 ; Macíček & Yordanov, 1992); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).(C7H11N2)2[Hg2Cl6] | Z = 2 |
Mr = 860.23 | F(000) = 792 |
Triclinic, P1 | Dx = 2.454 Mg m−3 |
a = 7.6558 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.8961 (5) Å | Cell parameters from 25 reflections |
c = 13.5853 (4) Å | θ = 10–15° |
α = 82.950 (3)° | µ = 13.87 mm−1 |
β = 76.072 (3)° | T = 293 K |
γ = 76.339 (4)° | Parallelepiped, colorless |
V = 1164.07 (8) Å3 | 0.72 × 0.24 × 0.18 mm |
Enraf–Nonius CAD-4 diffractometer | 3913 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 28.5°, θmin = 2.3° |
ω/2θ scans | h = −10→2 |
Absorption correction: ψ scan (North et al., 1968) | k = −15→15 |
Tmin = 0.53, Tmax = 0.99 | l = −18→18 |
7139 measured reflections | 2 standard reflections every 120 reflections |
5875 independent reflections | intensity decay: 1% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0933P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.153 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 3.41 e Å−3 |
5875 reflections | Δρmin = −3.00 e Å−3 |
236 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0058 (5) |
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 | ||
Hg1 | 0.73846 (6) | 0.52983 (3) | 0.96401 (3) | 0.04867 (15) | |
Hg2 | 0.70787 (6) | 0.02376 (3) | 0.53548 (3) | 0.05017 (16) | |
Cl3 | 0.7012 (4) | 0.6752 (2) | 0.82926 (18) | 0.0507 (6) | |
Cl5 | 0.5562 (4) | 0.1596 (2) | 0.66140 (18) | 0.0518 (6) | |
Cl2 | 0.4827 (3) | 0.5982 (2) | 1.11547 (17) | 0.0489 (6) | |
Cl6 | 0.5814 (4) | 0.1067 (2) | 0.37887 (17) | 0.0487 (5) | |
Cl1 | 0.9450 (4) | 0.3586 (2) | 1.0069 (2) | 0.0507 (6) | |
Cl4 | 0.9497 (4) | −0.1420 (2) | 0.5038 (2) | 0.0544 (6) | |
N1B | 0.3722 (13) | 0.0129 (9) | 0.8551 (6) | 0.055 (2) | |
H1B | 0.423341 | 0.022921 | 0.791911 | 0.067* | |
N1A | 0.6907 (12) | 0.5280 (8) | 0.6462 (6) | 0.047 (2) | |
H1A | 0.665775 | 0.537818 | 0.710142 | 0.056* | |
N2B | 0.1208 (12) | −0.0324 (7) | 1.1557 (6) | 0.0441 (18) | |
C1B | 0.2047 (12) | −0.0182 (8) | 1.0590 (6) | 0.0359 (19) | |
C5B | 0.2580 (14) | 0.0880 (8) | 1.0172 (8) | 0.043 (2) | |
H5B | 0.237846 | 0.149257 | 1.057848 | 0.051* | |
N2A | 0.8004 (12) | 0.4827 (8) | 0.3413 (6) | 0.047 (2) | |
C2A | 0.7198 (13) | 0.4105 (8) | 0.5161 (8) | 0.042 (2) | |
H2A | 0.712530 | 0.340021 | 0.496158 | 0.050* | |
C4B | 0.3388 (16) | 0.0977 (10) | 0.9166 (9) | 0.058 (3) | |
H4B | 0.372259 | 0.167244 | 0.889581 | 0.069* | |
C1A | 0.7683 (12) | 0.4958 (8) | 0.4424 (6) | 0.0352 (18) | |
C2B | 0.2482 (14) | −0.1070 (9) | 0.9916 (7) | 0.043 (2) | |
H2B | 0.223027 | −0.179339 | 1.015900 | 0.052* | |
C3B | 0.3261 (15) | −0.0884 (10) | 0.8918 (8) | 0.052 (3) | |
H3B | 0.347796 | −0.147079 | 0.848196 | 0.063* | |
C5A | 0.7751 (14) | 0.6032 (9) | 0.4768 (8) | 0.047 (2) | |
H5A | 0.805230 | 0.663582 | 0.430389 | 0.056* | |
C4A | 0.7372 (15) | 0.6156 (9) | 0.5779 (8) | 0.050 (2) | |
H4A | 0.742924 | 0.684838 | 0.600944 | 0.061* | |
C3A | 0.6831 (14) | 0.4271 (9) | 0.6157 (7) | 0.045 (2) | |
H3A | 0.652280 | 0.368100 | 0.663649 | 0.054* | |
C7B | 0.0765 (17) | 0.0644 (11) | 1.2239 (8) | 0.061 (3) | |
H7Q | 0.016344 | 0.039805 | 1.290807 | 0.091* | |
H7P | 0.188302 | 0.085789 | 1.227041 | 0.091* | |
H7D | −0.003486 | 0.129990 | 1.197662 | 0.091* | |
C6B | 0.0727 (16) | −0.1412 (10) | 1.1987 (8) | 0.058 (3) | |
H6Q | 0.013266 | −0.134628 | 1.269144 | 0.087* | |
H6D | −0.009493 | −0.159869 | 1.162861 | 0.087* | |
H6P | 0.182338 | −0.201411 | 1.192574 | 0.087* | |
C7A | 0.8505 (17) | 0.5720 (11) | 0.2661 (8) | 0.063 (3) | |
H7I | 0.867226 | 0.546304 | 0.199482 | 0.094* | |
H7J | 0.754609 | 0.640812 | 0.274933 | 0.094* | |
H7K | 0.963334 | 0.588643 | 0.273377 | 0.094* | |
C6A | 0.8007 (17) | 0.3711 (11) | 0.3057 (8) | 0.065 (3) | |
H6K | 0.825473 | 0.376560 | 0.232724 | 0.097* | |
H6I | 0.894286 | 0.311834 | 0.328549 | 0.097* | |
H6J | 0.682564 | 0.351849 | 0.332384 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.0531 (3) | 0.0467 (2) | 0.0452 (2) | −0.00220 (18) | −0.01806 (17) | −0.00119 (16) |
Hg2 | 0.0507 (3) | 0.0470 (3) | 0.0479 (2) | −0.00196 (18) | −0.00822 (17) | −0.00665 (17) |
Cl3 | 0.0702 (17) | 0.0420 (12) | 0.0451 (12) | −0.0111 (11) | −0.0240 (11) | −0.0015 (10) |
Cl5 | 0.0602 (15) | 0.0440 (13) | 0.0483 (12) | −0.0159 (11) | 0.0017 (11) | −0.0101 (10) |
Cl2 | 0.0486 (13) | 0.0604 (15) | 0.0393 (11) | −0.0136 (11) | −0.0069 (10) | −0.0111 (10) |
Cl6 | 0.0551 (14) | 0.0543 (14) | 0.0414 (11) | −0.0190 (11) | −0.0166 (10) | 0.0044 (10) |
Cl1 | 0.0547 (14) | 0.0363 (11) | 0.0709 (16) | −0.0105 (10) | −0.0348 (12) | 0.0018 (11) |
Cl4 | 0.0431 (13) | 0.0373 (12) | 0.0800 (18) | −0.0075 (10) | −0.0079 (12) | −0.0065 (11) |
N1B | 0.052 (5) | 0.072 (7) | 0.038 (4) | −0.005 (5) | −0.012 (4) | −0.002 (4) |
N1A | 0.057 (5) | 0.053 (5) | 0.034 (4) | −0.016 (4) | −0.011 (4) | −0.006 (4) |
N2B | 0.049 (5) | 0.048 (5) | 0.035 (4) | −0.012 (4) | −0.009 (3) | −0.004 (3) |
C1B | 0.030 (4) | 0.043 (5) | 0.035 (4) | 0.002 (3) | −0.018 (3) | −0.002 (4) |
C5B | 0.049 (5) | 0.028 (4) | 0.050 (5) | −0.001 (4) | −0.018 (4) | 0.000 (4) |
N2A | 0.041 (4) | 0.067 (6) | 0.033 (4) | −0.011 (4) | −0.007 (3) | −0.005 (4) |
C2A | 0.040 (5) | 0.035 (5) | 0.053 (5) | −0.006 (4) | −0.015 (4) | −0.007 (4) |
C4B | 0.050 (6) | 0.047 (6) | 0.072 (7) | −0.005 (5) | −0.021 (5) | 0.017 (5) |
C1A | 0.031 (4) | 0.042 (5) | 0.034 (4) | −0.007 (4) | −0.013 (3) | 0.001 (4) |
C2B | 0.046 (5) | 0.044 (5) | 0.043 (5) | −0.006 (4) | −0.019 (4) | −0.004 (4) |
C3B | 0.052 (6) | 0.061 (7) | 0.046 (5) | 0.004 (5) | −0.019 (5) | −0.026 (5) |
C5A | 0.049 (6) | 0.043 (5) | 0.051 (6) | −0.013 (4) | −0.018 (5) | 0.003 (4) |
C4A | 0.053 (6) | 0.038 (5) | 0.061 (6) | −0.004 (4) | −0.013 (5) | −0.014 (5) |
C3A | 0.046 (5) | 0.048 (6) | 0.041 (5) | −0.013 (4) | −0.008 (4) | 0.004 (4) |
C7B | 0.061 (7) | 0.080 (8) | 0.042 (5) | −0.014 (6) | −0.008 (5) | −0.019 (5) |
C6B | 0.064 (7) | 0.063 (7) | 0.051 (6) | −0.019 (6) | −0.019 (5) | 0.005 (5) |
C7A | 0.066 (7) | 0.074 (8) | 0.041 (5) | −0.013 (6) | −0.006 (5) | 0.013 (5) |
C6A | 0.068 (8) | 0.081 (9) | 0.048 (6) | −0.014 (7) | −0.011 (5) | −0.020 (6) |
Hg1—Cl1 | 2.371 (2) | C2A—C3A | 1.344 (14) |
Hg1—Cl3 | 2.380 (2) | C2A—C1A | 1.386 (13) |
Hg1—Cl2 | 2.539 (2) | C2A—H2A | 0.9300 |
Hg1—Cl2i | 2.975 (2) | C4B—H4B | 0.9300 |
Hg2—Cl4 | 2.367 (3) | C1A—C5A | 1.429 (13) |
Hg2—Cl5 | 2.392 (2) | C2B—C3B | 1.357 (15) |
Hg2—Cl6 | 2.542 (2) | C2B—H2B | 0.9300 |
Hg2—Cl6ii | 2.934 (3) | C3B—H3B | 0.9300 |
N1B—C4B | 1.329 (15) | C5A—C4A | 1.352 (15) |
N1B—C3B | 1.340 (15) | C5A—H5A | 0.9300 |
N1B—H1B | 0.8600 | C4A—H4A | 0.9300 |
N1A—C3A | 1.334 (13) | C3A—H3A | 0.9300 |
N1A—C4A | 1.362 (14) | C7B—H7Q | 0.9600 |
N1A—H1A | 0.8600 | C7B—H7P | 0.9600 |
N2B—C1B | 1.326 (12) | C7B—H7D | 0.9600 |
N2B—C6B | 1.445 (14) | C6B—H6Q | 0.9600 |
N2B—C7B | 1.492 (13) | C6B—H6D | 0.9600 |
C1B—C2B | 1.410 (13) | C6B—H6P | 0.9600 |
C1B—C5B | 1.429 (14) | C7A—H7I | 0.9600 |
C5B—C4B | 1.360 (15) | C7A—H7J | 0.9600 |
C5B—H5B | 0.9300 | C7A—H7K | 0.9600 |
N2A—C1A | 1.357 (11) | C6A—H6K | 0.9600 |
N2A—C7A | 1.435 (14) | C6A—H6I | 0.9600 |
N2A—C6A | 1.468 (15) | C6A—H6J | 0.9600 |
Cl1—Hg1—Cl3 | 141.44 (10) | C2A—C1A—C5A | 117.1 (8) |
Cl1—Hg1—Cl2 | 112.01 (9) | C3B—C2B—C1B | 121.0 (10) |
Cl3—Hg1—Cl2 | 106.16 (9) | C3B—C2B—H2B | 119.5 |
Cl1—Hg1—Cl2i | 93.63 (8) | C1B—C2B—H2B | 119.5 |
Cl3—Hg1—Cl2i | 88.63 (8) | N1B—C3B—C2B | 121.1 (9) |
Cl2—Hg1—Cl2i | 94.45 (7) | N1B—C3B—H3B | 119.4 |
Cl4—Hg2—Cl5 | 141.70 (10) | C2B—C3B—H3B | 119.4 |
Cl4—Hg2—Cl6 | 112.72 (10) | C4A—C5A—C1A | 119.1 (10) |
Cl5—Hg2—Cl6 | 105.06 (9) | C4A—C5A—H5A | 120.5 |
Cl4—Hg2—Cl6ii | 95.28 (8) | C1A—C5A—H5A | 120.5 |
Cl5—Hg2—Cl6ii | 87.53 (8) | C5A—C4A—N1A | 120.7 (9) |
Cl6—Hg2—Cl6ii | 94.73 (7) | C5A—C4A—H4A | 119.6 |
Hg1—Cl2—Hg1i | 85.55 (7) | N1A—C4A—H4A | 119.6 |
Hg2—Cl6—Hg2ii | 85.27 (7) | N1A—C3A—C2A | 120.3 (9) |
C4B—N1B—C3B | 119.8 (9) | N1A—C3A—H3A | 119.9 |
C4B—N1B—H1B | 120.1 | C2A—C3A—H3A | 119.9 |
C3B—N1B—H1B | 120.1 | N2B—C7B—H7Q | 109.5 |
C3A—N1A—C4A | 121.2 (8) | N2B—C7B—H7P | 109.5 |
C3A—N1A—H1A | 119.4 | H7Q—C7B—H7P | 109.5 |
C4A—N1A—H1A | 119.4 | N2B—C7B—H7D | 109.5 |
C1B—N2B—C6B | 121.7 (9) | H7Q—C7B—H7D | 109.5 |
C1B—N2B—C7B | 120.2 (9) | H7P—C7B—H7D | 109.5 |
C6B—N2B—C7B | 118.1 (8) | N2B—C6B—H6Q | 109.5 |
N2B—C1B—C2B | 122.2 (9) | N2B—C6B—H6D | 109.5 |
N2B—C1B—C5B | 121.8 (9) | H6Q—C6B—H6D | 109.5 |
C2B—C1B—C5B | 116.1 (9) | N2B—C6B—H6P | 109.5 |
C4B—C5B—C1B | 118.6 (9) | H6Q—C6B—H6P | 109.5 |
C4B—C5B—H5B | 120.7 | H6D—C6B—H6P | 109.5 |
C1B—C5B—H5B | 120.7 | N2A—C7A—H7I | 109.5 |
C1A—N2A—C7A | 122.1 (9) | N2A—C7A—H7J | 109.5 |
C1A—N2A—C6A | 120.1 (9) | H7I—C7A—H7J | 109.5 |
C7A—N2A—C6A | 117.6 (9) | N2A—C7A—H7K | 109.5 |
C3A—C2A—C1A | 121.6 (9) | H7I—C7A—H7K | 109.5 |
C3A—C2A—H2A | 119.2 | H7J—C7A—H7K | 109.5 |
C1A—C2A—H2A | 119.2 | N2A—C6A—H6K | 109.5 |
N1B—C4B—C5B | 123.3 (11) | N2A—C6A—H6I | 109.5 |
N1B—C4B—H4B | 118.4 | H6K—C6A—H6I | 109.5 |
C5B—C4B—H4B | 118.4 | N2A—C6A—H6J | 109.5 |
N2A—C1A—C2A | 122.8 (9) | H6K—C6A—H6J | 109.5 |
N2A—C1A—C5A | 120.0 (9) | H6I—C6A—H6J | 109.5 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···Cl3 | 0.86 | 2.54 | 3.239 (8) | 140 |
N1B—H1B···Cl5 | 0.86 | 2.46 | 3.195 (10) | 145 |
C2B—H2B···Cl1iii | 0.93 | 2.82 | 3.634 (11) | 147 |
C3A—H3A···Cl5 | 0.93 | 2.75 | 3.485 (11) | 136 |
Symmetry code: (iii) −x+1, −y, −z+2. |
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