![e logo](https://journals.iucr.org/logos/jicons/e_36x36.png)
![Open Access](/logos/buttonlogos/open.png)
![...](/logos/entities/ctdot_rmgif.gif)
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901502349X/im2475sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S205698901502349X/im2475Isup2.hkl |
CCDC reference: 1440754
Benzimidazole derivatives are reported to be physiologically and pharmacologically active (Tiwari, et al., 2007) and have shown different therapeutic properties such as antihypertensive, anticoagulant, antiallergic, analgesic, anti-inflammatory, antimicrobial, antiparasitic and antioxidant (Thimme Gowda, et al., 2009). Because of their significant medicinal importance, the synthesis of substituted benzimidazoles has become a focus of synthetic organic chemistry (Sondhi, et al., 2010). Benzimidazoles act as good ligands towards transition metal ions and give place to a variety of metal-ligand coordination modes. Their reactions with metal salts have played a significant role in the development of coordination chemistry of this class of ligands (Téllez, et al., 2008). Several research groups have investigated the coordination behavior of benzimidazole derivatives towards transition metal ions (Sundberg & Martin 1974; Reedijk, 1987) and numerous studies concerned with the biological activity of coordination compounds containing benzimidazole derivatives are also in progress.
Herein, we report the synthesis and structure determination of a new complex based on mercury and a chelating bis-benzimidazole ligand. The molecular structure of (I) together with the atomic numbering scheme is illustrated in Fig. 1.
In the asymmetric unit of [HgCl2(C16H14N4S)], (I), the HgII cation is linked to two chlorine atoms and two imidazole N atoms of the chelating ligand bis((1H-benzo[d]imidazol-2-yl)methyl)sulfane forming a slightly distorted tetrahedral environment [Hg—N = 2.2991 (19) and 2.2471 (19)Å; Hg—Cl = 2.4459 (7) and 2.4554 (7)Å].
Substitued imidazole rings of the ligand are almost perfectly planar [with maximum deviation of 0.0170 (26) Å at C13 and 0.0121 (28) Å at C5] and form a dihedral angle of 42.51 (5)°.
The crystal packing can be described by alternating layers parallel to (010) (Figure 2). In this arragement N—H···Cl hydrogen bonds between amine moities and chloride ligands are responsible for the formation of the one-dimensional chain-like packing pattern exhibiting a C11(6) graph set motif (Etter et al., 1990; Bernstein et al., 1995). Additional hydrogen-bonding parameters are listed in Table 1. The packing is consolidated by π-π stacking interactions with centroid to centroid distances of 3.5525 (14) to 3.6963 (14)Å between benzimidazole rings. These interactions link the molecules within the layers and also link the layers together reinforcing the cohesion of the complex structure.
Complex I was prepared by stirring 294 mg (1 mmol) of bis((1H-benzo[d]imidazol-2-yl)methyl)sulfane and 271 mg (1 mmol) HgCl2 in 20 mL of methanol for 24 h. The obtained solid was filtered and recrystallized by diffusion of diethyl ether into a DMF solution of the title compound at room temperature. Colorless crystals (yield: 83%) suitable for the X-ray diffraction study were obtained by this procedure.
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were localized on Fourier maps but introduced into calculated positions and treated as riding on their parent atom (C or N) with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and N—H = 0.86 Å (amine) with Uiso(H) = 1.2Ueq (C or N).
Benzimidazole derivatives are reported to be physiologically and pharmacologically active (Tiwari, et al., 2007) and have shown different therapeutic properties such as antihypertensive, anticoagulant, antiallergic, analgesic, anti-inflammatory, antimicrobial, antiparasitic and antioxidant (Thimme Gowda, et al., 2009). Because of their significant medicinal importance, the synthesis of substituted benzimidazoles has become a focus of synthetic organic chemistry (Sondhi, et al., 2010). Benzimidazoles act as good ligands towards transition metal ions and give place to a variety of metal-ligand coordination modes. Their reactions with metal salts have played a significant role in the development of coordination chemistry of this class of ligands (Téllez, et al., 2008). Several research groups have investigated the coordination behavior of benzimidazole derivatives towards transition metal ions (Sundberg & Martin 1974; Reedijk, 1987) and numerous studies concerned with the biological activity of coordination compounds containing benzimidazole derivatives are also in progress.
Herein, we report the synthesis and structure determination of a new complex based on mercury and a chelating bis-benzimidazole ligand. The molecular structure of (I) together with the atomic numbering scheme is illustrated in Fig. 1.
In the asymmetric unit of [HgCl2(C16H14N4S)], (I), the HgII cation is linked to two chlorine atoms and two imidazole N atoms of the chelating ligand bis((1H-benzo[d]imidazol-2-yl)methyl)sulfane forming a slightly distorted tetrahedral environment [Hg—N = 2.2991 (19) and 2.2471 (19)Å; Hg—Cl = 2.4459 (7) and 2.4554 (7)Å].
Substitued imidazole rings of the ligand are almost perfectly planar [with maximum deviation of 0.0170 (26) Å at C13 and 0.0121 (28) Å at C5] and form a dihedral angle of 42.51 (5)°.
The crystal packing can be described by alternating layers parallel to (010) (Figure 2). In this arragement N—H···Cl hydrogen bonds between amine moities and chloride ligands are responsible for the formation of the one-dimensional chain-like packing pattern exhibiting a C11(6) graph set motif (Etter et al., 1990; Bernstein et al., 1995). Additional hydrogen-bonding parameters are listed in Table 1. The packing is consolidated by π-π stacking interactions with centroid to centroid distances of 3.5525 (14) to 3.6963 (14)Å between benzimidazole rings. These interactions link the molecules within the layers and also link the layers together reinforcing the cohesion of the complex structure.
For the synthesis and applications of benzimiazole derivatives, see: Tiwari et al. (2007); Gowda et al. (2009); Sondhi et al., (2010). For the coordination of benzimiazole derivatives, see: Téllez et al. (2008); Sundberg & Martin (1974); Reedijk (1987).
Complex I was prepared by stirring 294 mg (1 mmol) of bis((1H-benzo[d]imidazol-2-yl)methyl)sulfane and 271 mg (1 mmol) HgCl2 in 20 mL of methanol for 24 h. The obtained solid was filtered and recrystallized by diffusion of diethyl ether into a DMF solution of the title compound at room temperature. Colorless crystals (yield: 83%) suitable for the X-ray diffraction study were obtained by this procedure.
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were localized on Fourier maps but introduced into calculated positions and treated as riding on their parent atom (C or N) with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and N—H = 0.86 Å (amine) with Uiso(H) = 1.2Ueq (C or N).
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXT (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).
[HgCl2(C16H14N4S)] | Dx = 2.173 Mg m−3 |
Mr = 565.86 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9958 reflections |
a = 13.8558 (3) Å | θ = 2.3–29.6° |
b = 15.4983 (4) Å | µ = 9.33 mm−1 |
c = 16.1108 (4) Å | T = 295 K |
V = 3459.66 (14) Å3 | Prism, colorless |
Z = 8 | 0.16 × 0.11 × 0.09 mm |
F(000) = 2144 |
Bruker APEXII diffractometer | 5594 independent reflections |
Radiation source: Enraf Nonius FR590 | 4351 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
CCD rotation images, thick slices scans | θmax = 31.2°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −20→20 |
Tmin = 0.646, Tmax = 0.746 | k = −22→22 |
78309 measured reflections | l = −22→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0162P)2 + 4.119P] where P = (Fo2 + 2Fc2)/3 |
5594 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.86 e Å−3 |
0 restraints | Δρmin = −0.93 e Å−3 |
[HgCl2(C16H14N4S)] | V = 3459.66 (14) Å3 |
Mr = 565.86 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.8558 (3) Å | µ = 9.33 mm−1 |
b = 15.4983 (4) Å | T = 295 K |
c = 16.1108 (4) Å | 0.16 × 0.11 × 0.09 mm |
Bruker APEXII diffractometer | 5594 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 4351 reflections with I > 2σ(I) |
Tmin = 0.646, Tmax = 0.746 | Rint = 0.035 |
78309 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 0 restraints |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.86 e Å−3 |
5594 reflections | Δρmin = −0.93 e Å−3 |
217 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.02521 (16) | 0.28013 (15) | 0.20752 (14) | 0.0275 (5) | |
C2 | −0.08439 (18) | 0.21383 (18) | 0.17932 (16) | 0.0350 (5) | |
H2 | −0.0882 | 0.1613 | 0.207 | 0.042* | |
C3 | −0.13721 (19) | 0.2296 (2) | 0.10828 (17) | 0.0425 (7) | |
H3 | −0.1779 | 0.1868 | 0.088 | 0.051* | |
C4 | −0.1311 (2) | 0.3079 (2) | 0.06612 (17) | 0.0447 (7) | |
H4 | −0.1673 | 0.3155 | 0.0181 | 0.054* | |
C5 | −0.07323 (19) | 0.3743 (2) | 0.09337 (17) | 0.0404 (6) | |
H5 | −0.0696 | 0.4266 | 0.0652 | 0.048* | |
C6 | −0.02053 (17) | 0.35897 (16) | 0.16529 (15) | 0.0289 (5) | |
C7 | 0.07692 (16) | 0.36125 (15) | 0.27412 (15) | 0.0272 (5) | |
C8 | 0.14891 (18) | 0.39298 (16) | 0.33483 (16) | 0.0332 (5) | |
H8A | 0.193 | 0.4319 | 0.3068 | 0.04* | |
H8B | 0.1862 | 0.3444 | 0.3551 | 0.04* | |
C9 | 0.0330 (2) | 0.36181 (17) | 0.47575 (17) | 0.0355 (5) | |
H9A | −0.0062 | 0.3861 | 0.5198 | 0.043* | |
H9B | −0.0101 | 0.3339 | 0.4366 | 0.043* | |
C10 | 0.09852 (17) | 0.29578 (15) | 0.51189 (14) | 0.0272 (4) | |
C11 | 0.17866 (16) | 0.17664 (14) | 0.53263 (14) | 0.0247 (4) | |
C12 | 0.21845 (18) | 0.09428 (16) | 0.52899 (16) | 0.0321 (5) | |
H12 | 0.2047 | 0.0568 | 0.4855 | 0.039* | |
C13 | 0.27933 (19) | 0.07089 (18) | 0.59296 (17) | 0.0388 (6) | |
H13 | 0.3068 | 0.0161 | 0.5925 | 0.047* | |
C14 | 0.30100 (19) | 0.12684 (19) | 0.65845 (17) | 0.0394 (6) | |
H14 | 0.3426 | 0.1085 | 0.7001 | 0.047* | |
C15 | 0.26224 (19) | 0.20829 (18) | 0.66267 (16) | 0.0362 (6) | |
H15 | 0.277 | 0.2458 | 0.7059 | 0.043* | |
C16 | 0.19957 (16) | 0.23173 (15) | 0.59886 (14) | 0.0274 (5) | |
N1 | 0.03651 (14) | 0.28386 (12) | 0.27585 (12) | 0.0272 (4) | |
N2 | 0.11618 (14) | 0.21920 (12) | 0.47882 (12) | 0.0268 (4) | |
N3 | 0.04426 (15) | 0.40839 (13) | 0.20965 (13) | 0.0311 (4) | |
H3N | 0.061 | 0.4605 | 0.1981 | 0.037* | |
N4 | 0.14764 (15) | 0.30614 (13) | 0.58354 (12) | 0.0310 (4) | |
H4N | 0.1468 | 0.3514 | 0.6144 | 0.037* | |
S1 | 0.09600 (6) | 0.44882 (4) | 0.42297 (4) | 0.04249 (16) | |
Cl1 | −0.09138 (5) | 0.08943 (4) | 0.37366 (4) | 0.04179 (15) | |
Cl2 | 0.17398 (6) | 0.08112 (5) | 0.27101 (5) | 0.0583 (2) | |
Hg1 | 0.063397 (7) | 0.164790 (6) | 0.357762 (6) | 0.03372 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0263 (10) | 0.0325 (12) | 0.0237 (11) | 0.0028 (9) | 0.0011 (9) | −0.0008 (9) |
C2 | 0.0365 (13) | 0.0382 (14) | 0.0305 (13) | −0.0066 (10) | −0.0014 (10) | −0.0039 (11) |
C3 | 0.0328 (13) | 0.0611 (19) | 0.0336 (14) | −0.0083 (12) | −0.0045 (11) | −0.0068 (13) |
C4 | 0.0345 (13) | 0.072 (2) | 0.0279 (13) | 0.0039 (13) | −0.0069 (11) | 0.0007 (13) |
C5 | 0.0421 (14) | 0.0491 (16) | 0.0301 (13) | 0.0088 (12) | 0.0002 (11) | 0.0075 (12) |
C6 | 0.0299 (11) | 0.0332 (12) | 0.0236 (11) | 0.0046 (9) | 0.0023 (9) | 0.0005 (9) |
C7 | 0.0309 (11) | 0.0238 (10) | 0.0268 (11) | 0.0003 (8) | 0.0015 (9) | 0.0001 (9) |
C8 | 0.0380 (12) | 0.0284 (12) | 0.0331 (13) | −0.0074 (10) | −0.0037 (10) | −0.0004 (10) |
C9 | 0.0421 (13) | 0.0332 (12) | 0.0311 (13) | 0.0104 (11) | 0.0032 (11) | −0.0015 (10) |
C10 | 0.0309 (11) | 0.0270 (11) | 0.0238 (11) | 0.0008 (9) | 0.0030 (9) | −0.0001 (9) |
C11 | 0.0265 (10) | 0.0259 (11) | 0.0216 (10) | −0.0032 (8) | 0.0019 (8) | 0.0019 (8) |
C12 | 0.0374 (12) | 0.0281 (11) | 0.0309 (13) | 0.0009 (10) | 0.0024 (10) | −0.0010 (10) |
C13 | 0.0382 (13) | 0.0357 (13) | 0.0426 (15) | 0.0062 (11) | 0.0017 (11) | 0.0098 (11) |
C14 | 0.0355 (13) | 0.0461 (15) | 0.0366 (15) | −0.0004 (12) | −0.0050 (11) | 0.0117 (12) |
C15 | 0.0407 (14) | 0.0405 (14) | 0.0274 (12) | −0.0082 (11) | −0.0055 (10) | 0.0009 (10) |
C16 | 0.0299 (11) | 0.0272 (11) | 0.0250 (11) | −0.0042 (9) | 0.0020 (9) | 0.0019 (9) |
N1 | 0.0315 (9) | 0.0242 (9) | 0.0259 (10) | −0.0014 (7) | −0.0034 (8) | 0.0016 (8) |
N2 | 0.0299 (9) | 0.0253 (9) | 0.0252 (10) | −0.0001 (7) | 0.0000 (8) | −0.0015 (8) |
N3 | 0.0395 (11) | 0.0247 (9) | 0.0291 (10) | −0.0005 (8) | −0.0004 (8) | 0.0045 (8) |
N4 | 0.0426 (11) | 0.0249 (9) | 0.0254 (10) | −0.0004 (8) | 0.0015 (9) | −0.0043 (8) |
S1 | 0.0708 (5) | 0.0221 (3) | 0.0345 (3) | 0.0013 (3) | −0.0047 (3) | −0.0040 (3) |
Cl1 | 0.0454 (3) | 0.0340 (3) | 0.0460 (4) | −0.0095 (3) | 0.0061 (3) | −0.0095 (3) |
Cl2 | 0.0735 (5) | 0.0413 (4) | 0.0601 (5) | 0.0137 (4) | 0.0196 (4) | −0.0056 (3) |
Hg1 | 0.04398 (6) | 0.02599 (5) | 0.03120 (5) | −0.00193 (4) | −0.00583 (4) | −0.00131 (4) |
C1—C2 | 1.391 (3) | C9—H9B | 0.97 |
C1—N1 | 1.395 (3) | C10—N2 | 1.324 (3) |
C1—C6 | 1.400 (3) | C10—N4 | 1.350 (3) |
C2—C3 | 1.380 (4) | C11—N2 | 1.391 (3) |
C2—H2 | 0.93 | C11—C12 | 1.392 (3) |
C3—C4 | 1.393 (4) | C11—C16 | 1.397 (3) |
C3—H3 | 0.93 | C12—C13 | 1.380 (4) |
C4—C5 | 1.378 (4) | C12—H12 | 0.93 |
C4—H4 | 0.93 | C13—C14 | 1.398 (4) |
C5—C6 | 1.390 (4) | C13—H13 | 0.93 |
C5—H5 | 0.93 | C14—C15 | 1.373 (4) |
C6—N3 | 1.380 (3) | C14—H14 | 0.93 |
C7—N1 | 1.324 (3) | C15—C16 | 1.394 (3) |
C7—N3 | 1.348 (3) | C15—H15 | 0.93 |
C7—C8 | 1.481 (3) | C16—N4 | 1.382 (3) |
C8—S1 | 1.817 (3) | N1—Hg1 | 2.2991 (19) |
C8—H8A | 0.97 | N2—Hg1 | 2.2471 (19) |
C8—H8B | 0.97 | N3—H3N | 0.86 |
C9—C10 | 1.487 (3) | N4—H4N | 0.86 |
C9—S1 | 1.818 (3) | Cl1—Hg1 | 2.4554 (7) |
C9—H9A | 0.97 | Cl2—Hg1 | 2.4459 (7) |
C2—C1—N1 | 130.5 (2) | N2—C11—C16 | 108.38 (19) |
C2—C1—C6 | 120.9 (2) | C12—C11—C16 | 120.7 (2) |
N1—C1—C6 | 108.6 (2) | C13—C12—C11 | 116.8 (2) |
C3—C2—C1 | 116.9 (3) | C13—C12—H12 | 121.6 |
C3—C2—H2 | 121.5 | C11—C12—H12 | 121.6 |
C1—C2—H2 | 121.5 | C12—C13—C14 | 122.1 (3) |
C2—C3—C4 | 121.8 (3) | C12—C13—H13 | 118.9 |
C2—C3—H3 | 119.1 | C14—C13—H13 | 118.9 |
C4—C3—H3 | 119.1 | C15—C14—C13 | 121.6 (2) |
C5—C4—C3 | 122.1 (3) | C15—C14—H14 | 119.2 |
C5—C4—H4 | 119 | C13—C14—H14 | 119.2 |
C3—C4—H4 | 119 | C14—C15—C16 | 116.5 (2) |
C4—C5—C6 | 116.3 (3) | C14—C15—H15 | 121.7 |
C4—C5—H5 | 121.8 | C16—C15—H15 | 121.7 |
C6—C5—H5 | 121.8 | N4—C16—C15 | 132.4 (2) |
N3—C6—C5 | 132.7 (2) | N4—C16—C11 | 105.41 (19) |
N3—C6—C1 | 105.2 (2) | C15—C16—C11 | 122.2 (2) |
C5—C6—C1 | 122.0 (2) | C7—N1—C1 | 106.27 (19) |
N1—C7—N3 | 111.4 (2) | C7—N1—Hg1 | 132.12 (16) |
N1—C7—C8 | 124.9 (2) | C1—N1—Hg1 | 121.26 (15) |
N3—C7—C8 | 123.7 (2) | C10—N2—C11 | 106.81 (19) |
C7—C8—S1 | 113.73 (18) | C10—N2—Hg1 | 128.73 (16) |
C7—C8—H8A | 108.8 | C11—N2—Hg1 | 124.43 (14) |
S1—C8—H8A | 108.8 | C7—N3—C6 | 108.5 (2) |
C7—C8—H8B | 108.8 | C7—N3—H3N | 125.8 |
S1—C8—H8B | 108.8 | C6—N3—H3N | 125.8 |
H8A—C8—H8B | 107.7 | C10—N4—C16 | 108.43 (19) |
C10—C9—S1 | 113.62 (19) | C10—N4—H4N | 125.8 |
C10—C9—H9A | 108.8 | C16—N4—H4N | 125.8 |
S1—C9—H9A | 108.8 | C8—S1—C9 | 101.89 (12) |
C10—C9—H9B | 108.8 | N2—Hg1—N1 | 104.46 (7) |
S1—C9—H9B | 108.8 | N2—Hg1—Cl2 | 119.40 (5) |
H9A—C9—H9B | 107.7 | N1—Hg1—Cl2 | 101.48 (5) |
N2—C10—N4 | 111.0 (2) | N2—Hg1—Cl1 | 111.85 (5) |
N2—C10—C9 | 124.9 (2) | N1—Hg1—Cl1 | 107.47 (5) |
N4—C10—C9 | 124.1 (2) | Cl2—Hg1—Cl1 | 110.77 (3) |
N2—C11—C12 | 130.9 (2) | ||
N1—C1—C2—C3 | −179.5 (2) | C2—C1—N1—Hg1 | 5.2 (3) |
C6—C1—C2—C3 | 0.3 (4) | C6—C1—N1—Hg1 | −174.53 (15) |
C1—C2—C3—C4 | 0.6 (4) | N4—C10—N2—C11 | 1.2 (3) |
C2—C3—C4—C5 | −0.9 (5) | C9—C10—N2—C11 | −178.4 (2) |
C3—C4—C5—C6 | 0.3 (4) | N4—C10—N2—Hg1 | −176.69 (15) |
C4—C5—C6—N3 | 179.2 (3) | C9—C10—N2—Hg1 | 3.7 (3) |
C4—C5—C6—C1 | 0.5 (4) | C12—C11—N2—C10 | 178.5 (2) |
C2—C1—C6—N3 | −179.8 (2) | C16—C11—N2—C10 | −1.2 (2) |
N1—C1—C6—N3 | 0.0 (3) | C12—C11—N2—Hg1 | −3.4 (3) |
C2—C1—C6—C5 | −0.8 (4) | C16—C11—N2—Hg1 | 176.80 (14) |
N1—C1—C6—C5 | 178.9 (2) | N1—C7—N3—C6 | −0.9 (3) |
N1—C7—C8—S1 | −91.1 (3) | C8—C7—N3—C6 | 179.1 (2) |
N3—C7—C8—S1 | 88.9 (3) | C5—C6—N3—C7 | −178.3 (3) |
S1—C9—C10—N2 | −102.2 (3) | C1—C6—N3—C7 | 0.6 (3) |
S1—C9—C10—N4 | 78.2 (3) | N2—C10—N4—C16 | −0.8 (3) |
N2—C11—C12—C13 | 179.7 (2) | C9—C10—N4—C16 | 178.9 (2) |
C16—C11—C12—C13 | −0.6 (3) | C15—C16—N4—C10 | 179.2 (3) |
C11—C12—C13—C14 | −0.3 (4) | C11—C16—N4—C10 | 0.0 (3) |
C12—C13—C14—C15 | 0.3 (4) | C7—C8—S1—C9 | 67.4 (2) |
C13—C14—C15—C16 | 0.7 (4) | C10—C9—S1—C8 | 67.0 (2) |
C14—C15—C16—N4 | 179.2 (2) | C10—N2—Hg1—N1 | 26.7 (2) |
C14—C15—C16—C11 | −1.6 (4) | C11—N2—Hg1—N1 | −150.88 (17) |
N2—C11—C16—N4 | 0.8 (2) | C10—N2—Hg1—Cl2 | 139.14 (18) |
C12—C11—C16—N4 | −179.0 (2) | C11—N2—Hg1—Cl2 | −38.46 (19) |
N2—C11—C16—C15 | −178.6 (2) | C10—N2—Hg1—Cl1 | −89.2 (2) |
C12—C11—C16—C15 | 1.6 (3) | C11—N2—Hg1—Cl1 | 93.18 (17) |
N3—C7—N1—C1 | 0.9 (3) | C7—N1—Hg1—N2 | 29.2 (2) |
C8—C7—N1—C1 | −179.1 (2) | C1—N1—Hg1—N2 | −158.52 (16) |
N3—C7—N1—Hg1 | 173.99 (16) | C7—N1—Hg1—Cl2 | −95.5 (2) |
C8—C7—N1—Hg1 | −6.0 (4) | C1—N1—Hg1—Cl2 | 76.74 (17) |
C2—C1—N1—C7 | 179.2 (3) | C7—N1—Hg1—Cl1 | 148.2 (2) |
C6—C1—N1—C7 | −0.5 (3) | C1—N1—Hg1—Cl1 | −39.57 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···Cl1i | 0.86 | 2.35 | 3.178 (2) | 163 |
N4—H4N···Cl2ii | 0.86 | 2.76 | 3.508 (2) | 147 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···Cl1i | 0.8600 | 2.3500 | 3.178 (2) | 163.00 |
N4—H4N···Cl2ii | 0.8600 | 2.7600 | 3.508 (2) | 147.00 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2. |