Tetrameric di­chloro­(tri­methyl­ammonio-p-toluene­sulfonamidate)­mercury(II)

In the title compound, hexa-[mu]-chloro-di­chloro­tetrakis(N-tri­methyl­ammonio-p-toluene­sulfonamidate-[kappa]²N,O)­tetramer­cury(II), [Hg{Me₃N(+)N(-)SO₂C₆H₄CH₃-p}Cl₂]₄ or [Hg₄Cl₈(C₁₀H₁₆N₂O₂S)₄], four nearly linear and parallel Cl-Hg-Cl units associate through pairwise Hg...Cl interactions of 3.1-3.2 Å. Each Hg atom is also coordinated through N and O atoms to a yl­ide mol­ecule. The available structural data indicate that coordination of a sulfonyl-stabilized nitro­gen yl­ide to a metal atom (Hg or Ag) has no detectable effect on its geometry.

S1. Comment

We have recently shown that trimethylammonio-stabilized nitrogen ylides, such as (Ia) or (Ib), can act as ligands, donating to silver(I) and mercury(II) through their negatively charged N atoms and sometimes also through an O atom (Morris et al., 2003). In an extension of this work, we now report the structure of the title complex, (II), a 1:1 adduct of the sulfonyl-stabilized ylide (Ia) with mercury(II) chloride. \sch

The asymmetric unit of (II) contains two HgCl₂L moieties [Fig. 1; L is (Ia)]. The discrete centrosymmetric tetrameric molecule shown in Fig. 2 is formed from two such asymmetric units. Each metal atom is strongly bonded to two Cl atoms [Hg—Cl 2.325 (1)–2.340 (1) Å; Table 1] and is thereby incorporated into a nearly linear Cl—Hg—Cl unit: the Cl11—Hg1—Cl12 and Cl21—Hg2—Cl22 angles are 167.6 (1) and 160.8 (1)°, respectively. The tetrameric molecule contains four such Cl—Hg—Cl units which are roughly parallel to one another, and they associate through pairs of weak Hg···Cl interactions [3.07–3.22 Å]. Each metal atom is also chelated by the N and O atoms of an ylide ligand, and the Hg—N and Hg—O distances [2.507 (2) and 2.831 (2) Å, respectively, for Hg1, and 2.492 (2) and 2.757 (2) Å, respectively, for Hg2] indicate that the stronger interaction is through the N atom. It is broadly true that, at each Hg atom, the Hg—N and Hg—O bonds are normal to the strong Hg—Cl bonds and coplanar with the weaker Hg···Cl interactions. Atom Hg1 has a distorted octahedral coordination formed by strong bonds to atoms Cl11 and Cl12, and weaker bonds to atoms Cl11ⁱ and Cl22 and to the N and O atoms of the ylide [symmetry code: (i) Please provide missing information]. In contrast, Hg2 adopts a distorted square-pyramidal coordination, with atom N21 apical. The Hg2 coordination can be compared with that of Hg1 when the Hg1···Cl11ⁱ interaction is ignored. The average difference between corresponding angles subtended at Hg1 and Hg2 is then only 5°.

The structure of (II) contrasts with that of the apparently analogous species, (III), [HgCl₂L], where L is (Ib) (Morris et al., 2003). In (III), linear Hg coordination is defined by strong Hg—N and Hg—Cl bonds of 2.154 (5) and 2.371 (2) Å, which are roughly normal to weak Hg—Cl bonds [2.596 (1) Å] and extremely weak Hg—O interactions [2.847 (4) Å]. The weaker Hg—Cl bond associates further with the corresponding bonds in adjacent units so that a chain coordination polymer is produced. Each metal atom has the same [2,2,2] distorted-octahedral coordination. Although the variable and as yet unpredictable nature of mercury(II) coordination polyhedra is well known (House et al., 1994), the difference of 0.35 Å between the Hg—N(ylide) bonds in (II) and (III) is particularly striking.

Bond lengths in the L = (Ia) ligands of (II) and of (IV), [AgNO₃L₂] (Morris et al., 2003), agree well with those in the monohydrate of (Ia) (Cameron et al., 1976), where the ylide N(-) atom is hydrogen-bonded to a water molecule. These species all contain single N—N and S—C bonds [1.464 (3)–1.481 (6) and 1.761 (7)–1.782 (2) Å, respectively], whereas the S—N distances [1.592 (2)–1.616 (5) Å] imply some multiple-bond character. The S—O distances [1.434 (4)–1.452 (2) Å] do not appear to lengthen when the O atom is coordinated to Hg or Ag. Indeed, it is hard to find evidence that attachment of the ylide to Hg or Ag requires even a conformational change. The (Ia) sulfonyl-ylide ligands in (II), in (IV) and in the monohydrate of (Ia) all adopt the conformation (V). i.e. a roughly planar H₃C—N(+)-N(-)-S—O^a zigzag chain with torsion angles of 156–173° across the N—N and N—S bonds. The N—S—O^a angles [103.0 (3)–104.1 (1)°] are invariably more acute than the N—S—O^b angles [113.0 (3)–115.4 (1)°]. In (II) and (IV), this could be ascribed to chelate ring formation. In the monohydrate of (Ia), hydrogen bonding is a complicating factor. However, in n-C₁₆H₃₃SO₂N(-)N(+)Me₃ (Morris & Muir, 2004), the same ylide conformation [N—N and N—S torsion angles 167 and 160°, respectively, N—S—O^a 103.3 (3) and N—S—O^b 114.5 (3)°] is found. This appears to be the stable conformation of an Me₃NNSO₂ ylide and we believe the near-eclipse implied by N—N—S—O^b torsion angles of 28–41° is responsible for the obtuseness of the N—S—O^b bond angles.

S2. Experimental

The methods of Morris et al. (2003) were used for the preparation of the ylide ligand and its complexation to mercury(II) chloride. Crystals of the title compound, (II), were obtained from aqueous solution.

S3. Refinement

H-atom positions were initially obtained from difference syntheses. Subsequently, all H atoms rode on their parent C atoms: for methyl H atoms, C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C), while for phenyl H atoms, C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). The final difference synthesis is indicative of some inadequacy in the absorption correction: all regions with |Δρ| > 1.5 e Å⁻³ are within 1 Å of an Hg atom.

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The asymmetric unit of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity.
	Fig. 2. The tetrameric molecule of (II). H atoms have been omitted for clarity.

(II)

Crystal data

[Hg4Cl8(C10H16N2O2S)4]	F(000) = 1888
Mr = 1999.2	Dx = 2.223 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12596 reflections
a = 7.9948 (1) Å	θ = 1.0–35.0°
b = 21.6336 (2) Å	µ = 10.8 mm^−1
c = 17.2957 (1) Å	T = 100 K
β = 93.3241 (3)°	Needle, colourless
V = 2986.37 (5) Å^3	0.35 × 0.15 × 0.15 mm
Z = 2

Data collection

Nonius KappaCCD area-detector diffractometer	11417 reflections with I > 2σ(I)
CCD; rotation images; thick slice scans	Rint = 0.058
Absorption correction: gaussian quadrature algorithm in WinGX KappaCCD processing package (Farrugia, 1999)	θmax = 35.0°, θmin = 1.9°
Tmin = 0.119, Tmax = 0.479	h = −12→12
59772 measured reflections	k = 0→34
12956 independent reflections	l = 0→27

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.037P)^2 + 2.14P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.026	(Δ/σ)max = 0.001
wR(F^2) = 0.068	Δρmax = 1.54 e Å^−3
S = 1.04	Δρmin = −3.59 e Å^−3
12956 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
326 parameters	Extinction coefficient: 0.00064 (5)
0 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Hg1	0.053972 (10)	0.078464 (4)	−0.053427 (5)	0.01396 (3)
Cl11	−0.20129 (7)	0.04476 (3)	−0.00995 (3)	0.01696 (10)
Cl12	0.32910 (7)	0.11122 (3)	−0.06866 (4)	0.01868 (10)
S11	−0.05506 (7)	0.05908 (3)	−0.24103 (3)	0.01312 (9)
O11	−0.2128 (2)	0.04745 (8)	−0.28384 (11)	0.0187 (3)
O12	0.0139 (2)	0.00961 (8)	−0.19247 (11)	0.0197 (3)
N11	−0.0537 (2)	0.11703 (9)	−0.18367 (12)	0.0134 (3)
N12	−0.1674 (2)	0.16889 (9)	−0.20102 (12)	0.0140 (3)
C11	−0.1693 (3)	0.19161 (12)	−0.28368 (16)	0.0196 (4)
H11A	−0.0553	0.2029	−0.2963	0.029*
H11B	−0.2423	0.2279	−0.2896	0.029*
H11C	−0.2116	0.1588	−0.3187	0.029*
C12	−0.0999 (3)	0.21963 (11)	−0.14939 (17)	0.0206 (5)
H12A	−0.1027	0.2066	−0.0952	0.031*
H12B	−0.1688	0.2568	−0.1578	0.031*
H12C	0.0158	0.2287	−0.1613	0.031*
C13	−0.3415 (3)	0.15286 (11)	−0.17939 (17)	0.0191 (4)
H13A	−0.3847	0.1185	−0.2117	0.029*
H13B	−0.4146	0.1889	−0.1876	0.029*
H13C	−0.3389	0.1407	−0.1248	0.029*
C14	0.0963 (3)	0.07157 (10)	−0.31052 (14)	0.0144 (4)
C15	0.0893 (3)	0.03578 (11)	−0.37765 (15)	0.0184 (4)
H15	−0.0027	0.0088	−0.3889	0.022*
C16	0.2182 (3)	0.03986 (12)	−0.42805 (16)	0.0216 (5)
H16	0.2144	0.0151	−0.4735	0.026*
C17	0.3538 (3)	0.08007 (12)	−0.41274 (17)	0.0198 (5)
C18	0.3545 (3)	0.11691 (12)	−0.34666 (16)	0.0194 (4)
H18	0.4437	0.1453	−0.3366	0.023*
C19	0.2282 (3)	0.11308 (11)	−0.29516 (15)	0.0167 (4)
H19	0.2312	0.1383	−0.2501	0.02*
C110	0.4995 (4)	0.08288 (13)	−0.46474 (19)	0.0271 (6)
H11D	0.5944	0.0597	−0.4409	0.041*
H11E	0.5323	0.1261	−0.4718	0.041*
H11F	0.466	0.0647	−0.5152	0.041*
Hg2	0.337715 (10)	0.200763 (4)	0.068872 (5)	0.01582 (3)
Cl21	0.59800 (7)	0.23835 (3)	0.03790 (4)	0.02143 (11)
Cl22	0.04783 (7)	0.18898 (3)	0.07074 (4)	0.02211 (11)
S21	0.42431 (7)	0.18537 (2)	0.25504 (3)	0.01276 (9)
O21	0.3598 (2)	0.24227 (8)	0.21985 (11)	0.0197 (3)
O22	0.5840 (2)	0.18913 (9)	0.29925 (11)	0.0189 (3)
N21	0.4193 (2)	0.13698 (9)	0.18496 (11)	0.0124 (3)
N22	0.5321 (2)	0.08358 (9)	0.19065 (12)	0.0137 (3)
C21	0.7061 (3)	0.10244 (12)	0.17127 (15)	0.0191 (4)
H21A	0.7018	0.1219	0.12	0.029*
H21B	0.7782	0.0658	0.171	0.029*
H21C	0.7515	0.1318	0.2102	0.029*
C22	0.5347 (3)	0.05037 (11)	0.26715 (15)	0.0183 (4)
H22A	0.5768	0.0783	0.3085	0.027*
H22B	0.6081	0.0142	0.2655	0.027*
H22C	0.4209	0.037	0.2773	0.027*
C23	0.4604 (3)	0.04021 (12)	0.12978 (16)	0.0206 (5)
H23A	0.346	0.0289	0.1416	0.031*
H23B	0.5298	0.0029	0.1288	0.031*
H23C	0.4585	0.0605	0.0791	0.031*
C24	0.2734 (3)	0.16300 (10)	0.32070 (14)	0.0138 (4)
C25	0.1299 (3)	0.13094 (11)	0.29354 (14)	0.0166 (4)
H25	0.1185	0.1165	0.2416	0.02*
C26	0.0039 (3)	0.12073 (12)	0.34452 (16)	0.0192 (4)
H26	−0.0941	0.0989	0.3268	0.023*
C27	0.0181 (3)	0.14160 (12)	0.42067 (16)	0.0188 (4)
C28	0.1650 (3)	0.17182 (12)	0.44649 (16)	0.0214 (5)
H28	0.1782	0.1851	0.4988	0.026*
C29	0.2928 (3)	0.18283 (12)	0.39688 (15)	0.0182 (4)
H29	0.3921	0.2037	0.415	0.022*
C210	−0.1231 (4)	0.13362 (15)	0.47276 (19)	0.0285 (6)
H21D	−0.1338	0.1709	0.5043	0.043*
H21E	−0.1006	0.098	0.5068	0.043*
H21F	−0.2276	0.1267	0.4414	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.01245 (4)	0.01628 (4)	0.01326 (4)	−0.00107 (2)	0.00162 (3)	0.00070 (3)
Cl11	0.0144 (2)	0.0205 (2)	0.0162 (2)	−0.00174 (17)	0.00284 (18)	0.00021 (19)
Cl12	0.0134 (2)	0.0239 (3)	0.0189 (3)	−0.00273 (18)	0.00272 (18)	−0.0004 (2)
S11	0.0132 (2)	0.0127 (2)	0.0137 (2)	0.00011 (16)	0.00232 (17)	0.00067 (18)
O11	0.0155 (7)	0.0190 (8)	0.0217 (9)	−0.0045 (6)	0.0016 (6)	−0.0050 (7)
O12	0.0265 (9)	0.0148 (7)	0.0182 (9)	0.0060 (6)	0.0044 (7)	0.0043 (6)
N11	0.0158 (8)	0.0123 (8)	0.0120 (8)	0.0048 (6)	−0.0013 (6)	−0.0005 (6)
N12	0.0121 (7)	0.0145 (8)	0.0154 (9)	0.0014 (6)	0.0006 (6)	0.0008 (7)
C11	0.0232 (11)	0.0180 (10)	0.0177 (11)	0.0042 (8)	0.0022 (9)	0.0071 (8)
C12	0.0210 (10)	0.0150 (10)	0.0252 (13)	0.0017 (8)	−0.0032 (9)	−0.0038 (9)
C13	0.0133 (9)	0.0172 (10)	0.0270 (13)	0.0020 (7)	0.0041 (8)	0.0016 (9)
C14	0.0140 (9)	0.0141 (9)	0.0153 (10)	0.0009 (7)	0.0027 (7)	0.0007 (7)
C15	0.0205 (10)	0.0169 (10)	0.0180 (11)	−0.0037 (8)	0.0032 (8)	−0.0022 (8)
C16	0.0278 (12)	0.0214 (11)	0.0163 (11)	−0.0026 (9)	0.0079 (9)	−0.0053 (9)
C17	0.0192 (10)	0.0190 (11)	0.0221 (12)	0.0012 (8)	0.0096 (9)	0.0009 (9)
C18	0.0171 (10)	0.0189 (10)	0.0224 (12)	−0.0030 (8)	0.0040 (8)	−0.0014 (9)
C19	0.0158 (9)	0.0169 (10)	0.0175 (11)	−0.0026 (7)	0.0019 (8)	−0.0034 (8)
C110	0.0293 (13)	0.0244 (13)	0.0291 (15)	−0.0002 (10)	0.0158 (12)	−0.0016 (11)
Hg2	0.01339 (4)	0.01853 (5)	0.01546 (5)	−0.00137 (3)	0.00012 (3)	0.00290 (3)
Cl21	0.0155 (2)	0.0249 (3)	0.0238 (3)	−0.00426 (19)	0.0010 (2)	0.0069 (2)
Cl22	0.0137 (2)	0.0290 (3)	0.0236 (3)	−0.0011 (2)	0.0013 (2)	0.0014 (2)
S21	0.0133 (2)	0.0121 (2)	0.0130 (2)	−0.00197 (16)	0.00280 (17)	−0.00141 (18)
O21	0.0276 (9)	0.0126 (7)	0.0194 (9)	0.0016 (6)	0.0054 (7)	0.0012 (6)
O22	0.0159 (7)	0.0230 (8)	0.0179 (9)	−0.0065 (6)	0.0020 (6)	−0.0066 (7)
N21	0.0144 (7)	0.0125 (8)	0.0103 (8)	0.0018 (6)	0.0002 (6)	−0.0008 (6)
N22	0.0143 (8)	0.0121 (8)	0.0144 (9)	0.0018 (6)	−0.0003 (7)	−0.0001 (6)
C21	0.0164 (10)	0.0239 (11)	0.0173 (11)	0.0033 (8)	0.0027 (8)	0.0002 (9)
C22	0.0231 (10)	0.0164 (10)	0.0153 (11)	0.0015 (8)	−0.0007 (8)	0.0042 (8)
C23	0.0258 (11)	0.0171 (10)	0.0185 (11)	0.0037 (8)	−0.0010 (9)	−0.0053 (9)
C24	0.0133 (8)	0.0137 (9)	0.0146 (10)	−0.0008 (7)	0.0019 (7)	−0.0018 (7)
C25	0.0152 (9)	0.0205 (10)	0.0141 (10)	−0.0032 (7)	−0.0007 (7)	−0.0013 (8)
C26	0.0149 (9)	0.0229 (11)	0.0198 (12)	−0.0023 (8)	0.0004 (8)	0.0043 (9)
C27	0.0177 (10)	0.0178 (10)	0.0215 (12)	0.0035 (8)	0.0072 (8)	0.0042 (9)
C28	0.0294 (12)	0.0205 (11)	0.0149 (11)	−0.0022 (9)	0.0069 (9)	−0.0051 (9)
C29	0.0206 (10)	0.0192 (10)	0.0151 (11)	−0.0033 (8)	0.0032 (8)	−0.0040 (8)
C210	0.0258 (12)	0.0307 (14)	0.0306 (15)	0.0046 (10)	0.0155 (11)	0.0071 (12)

Geometric parameters (Å, º)

Hg1—Cl11	2.3323 (5)	C110—H11F	0.98
Hg1—Cl12	2.3403 (5)	Hg2—Cl21	2.3254 (6)
Hg1—N11	2.507 (2)	Hg2—Cl22	2.3336 (6)
Hg1—O12	2.831 (2)	Hg2—N21	2.492 (2)
Hg1—Cl11^i	3.0896 (6)	Hg2—O21	2.757 (2)
Hg1—Cl22	3.2160 (7)	Hg2—S21	3.2711 (6)
Hg1—Hg1^i	3.9838 (2)	S21—O22	1.452 (2)
Cl12—Hg2	3.0654 (6)	S21—O21	1.454 (2)
S11—O11	1.447 (2)	S21—N21	1.600 (2)
S11—O12	1.450 (2)	S21—C24	1.771 (2)
S11—N11	1.598 (2)	N21—N22	1.465 (3)
S11—C14	1.775 (2)	N22—C23	1.499 (3)
N11—N12	1.464 (3)	N22—C22	1.505 (3)
N12—C12	1.496 (3)	N22—C21	1.506 (3)
N12—C13	1.503 (3)	C21—H21A	0.98
N12—C11	1.511 (3)	C21—H21B	0.98
C11—H11A	0.98	C21—H21C	0.98
C11—H11B	0.98	C22—H22A	0.98
C11—H11C	0.98	C22—H22B	0.98
C12—H12A	0.98	C22—H22C	0.98
C12—H12B	0.98	C23—H23A	0.98
C12—H12C	0.98	C23—H23B	0.98
C13—H13A	0.98	C23—H23C	0.98
C13—H13B	0.98	C24—C29	1.386 (3)
C13—H13C	0.98	C24—C25	1.399 (3)
C14—C15	1.394 (4)	C25—C26	1.394 (3)
C14—C19	1.398 (3)	C25—H25	0.95
C15—C16	1.390 (4)	C26—C27	1.391 (4)
C15—H15	0.95	C26—H26	0.95
C16—C17	1.403 (4)	C27—C28	1.395 (4)
C16—H16	0.95	C27—C210	1.495 (4)
C17—C18	1.393 (4)	C28—C29	1.392 (4)
C17—C110	1.513 (4)	C28—H28	0.95
C18—C19	1.387 (3)	C29—H29	0.95
C18—H18	0.95	C210—H21D	0.98
C19—H19	0.95	C210—H21E	0.98
C110—H11D	0.98	C210—H21F	0.98
C110—H11E	0.98
Cl11—Hg1—Cl12	167.59 (2)	H11E—C110—H11F	109.5
Cl11—Hg1—N11	97.60 (5)	Cl21—Hg2—Cl22	160.75 (2)
Cl12—Hg1—N11	94.26 (5)	Cl21—Hg2—N21	100.56 (5)
Cl11—Hg1—O12	92.94 (4)	Cl22—Hg2—N21	98.17 (5)
Cl12—Hg1—O12	97.16 (4)	Cl21—Hg2—O21	95.47 (4)
N11—Hg1—O12	52.83 (6)	Cl22—Hg2—O21	91.81 (4)
Cl11—Hg1—Cl11^i	86.479 (18)	N21—Hg2—O21	54.40 (6)
Cl12—Hg1—Cl11^i	87.692 (18)	Cl21—Hg2—Cl12	91.28 (2)
N11—Hg1—Cl11^i	135.22 (4)	Cl22—Hg2—Cl12	87.94 (2)
O12—Hg1—Cl11^i	82.50 (4)	N21—Hg2—Cl12	105.57 (4)
Cl11—Hg1—Cl22	88.257 (18)	O21—Hg2—Cl12	159.72 (4)
Cl12—Hg1—Cl22	84.313 (19)	Cl21—Hg2—S21	96.963 (19)
N11—Hg1—Cl22	109.56 (4)	Cl22—Hg2—S21	97.41 (2)
O12—Hg1—Cl22	162.36 (4)	N21—Hg2—S21	28.34 (4)
Cl11^i—Hg1—Cl22	115.138 (16)	O21—Hg2—S21	26.18 (4)
Cl11—Hg1—Hg1^i	50.722 (14)	Cl12—Hg2—S21	133.905 (15)
Cl12—Hg1—Hg1^i	122.720 (16)	Hg2—Cl22—Hg1	91.05 (2)
N11—Hg1—Hg1^i	128.90 (4)	O22—S21—O21	116.91 (11)
O12—Hg1—Hg1^i	85.92 (4)	O22—S21—N21	114.72 (10)
Cl11^i—Hg1—Hg1^i	35.757 (10)	O21—S21—N21	104.12 (11)
Cl22—Hg1—Hg1^i	108.158 (13)	O22—S21—C24	106.76 (11)
Hg1—Cl11—Hg1^i	93.521 (18)	O21—S21—C24	105.15 (11)
Hg1—Cl12—Hg2	94.76 (2)	N21—S21—C24	108.59 (10)
O11—S11—O12	117.32 (11)	O22—S21—Hg2	129.96 (8)
O11—S11—N11	115.36 (10)	O21—S21—Hg2	56.78 (8)
O12—S11—N11	103.34 (11)	N21—S21—Hg2	47.66 (7)
O11—S11—C14	106.75 (11)	C24—S21—Hg2	123.07 (8)
O12—S11—C14	104.68 (11)	S21—O21—Hg2	97.03 (9)
N11—S11—C14	108.71 (11)	N22—N21—S21	118.46 (15)
S11—O12—Hg1	97.14 (9)	N22—N21—Hg2	128.47 (14)
N12—N11—S11	119.48 (15)	S21—N21—Hg2	104.00 (9)
N12—N11—Hg1	128.02 (14)	N21—N22—C23	103.74 (17)
S11—N11—Hg1	106.64 (9)	N21—N22—C22	114.37 (18)
N11—N12—C12	104.01 (17)	C23—N22—C22	107.68 (19)
N11—N12—C13	110.18 (18)	N21—N22—C21	110.14 (17)
C12—N12—C13	109.1 (2)	C23—N22—C21	109.5 (2)
N11—N12—C11	114.54 (18)	C22—N22—C21	111.06 (18)
C12—N12—C11	108.04 (19)	N22—C21—H21A	109.5
C13—N12—C11	110.60 (19)	N22—C21—H21B	109.5
N12—C11—H11A	109.5	H21A—C21—H21B	109.5
N12—C11—H11B	109.5	N22—C21—H21C	109.5
H11A—C11—H11B	109.5	H21A—C21—H21C	109.5
N12—C11—H11C	109.5	H21B—C21—H21C	109.5
H11A—C11—H11C	109.5	N22—C22—H22A	109.5
H11B—C11—H11C	109.5	N22—C22—H22B	109.5
N12—C12—H12A	109.5	H22A—C22—H22B	109.5
N12—C12—H12B	109.5	N22—C22—H22C	109.5
H12A—C12—H12B	109.5	H22A—C22—H22C	109.5
N12—C12—H12C	109.5	H22B—C22—H22C	109.5
H12A—C12—H12C	109.5	N22—C23—H23A	109.5
H12B—C12—H12C	109.5	N22—C23—H23B	109.5
N12—C13—H13A	109.5	H23A—C23—H23B	109.5
N12—C13—H13B	109.5	N22—C23—H23C	109.5
H13A—C13—H13B	109.5	H23A—C23—H23C	109.5
N12—C13—H13C	109.5	H23B—C23—H23C	109.5
H13A—C13—H13C	109.5	C29—C24—C25	121.2 (2)
H13B—C13—H13C	109.5	C29—C24—S21	118.82 (17)
C15—C14—C19	120.6 (2)	C25—C24—S21	119.75 (18)
C15—C14—S11	118.91 (18)	C26—C25—C24	118.3 (2)
C19—C14—S11	120.34 (19)	C26—C25—H25	120.8
C16—C15—C14	119.4 (2)	C24—C25—H25	120.8
C16—C15—H15	120.3	C27—C26—C25	121.7 (2)
C14—C15—H15	120.3	C27—C26—H26	119.1
C15—C16—C17	120.9 (2)	C25—C26—H26	119.1
C15—C16—H16	119.5	C26—C27—C28	118.4 (2)
C17—C16—H16	119.5	C26—C27—C210	120.7 (2)
C18—C17—C16	118.4 (2)	C28—C27—C210	120.8 (3)
C18—C17—C110	119.9 (2)	C29—C28—C27	121.2 (2)
C16—C17—C110	121.7 (3)	C29—C28—H28	119.4
C19—C18—C17	121.6 (2)	C27—C28—H28	119.4
C19—C18—H18	119.2	C24—C29—C28	119.2 (2)
C17—C18—H18	119.2	C24—C29—H29	120.4
C18—C19—C14	119.0 (2)	C28—C29—H29	120.4
C18—C19—H19	120.5	C27—C210—H21D	109.5
C14—C19—H19	120.5	C27—C210—H21E	109.5
C17—C110—H11D	109.5	H21D—C210—H21E	109.5
C17—C110—H11E	109.5	C27—C210—H21F	109.5
H11D—C110—H11E	109.5	H21D—C210—H21F	109.5
C17—C110—H11F	109.5	H21E—C210—H21F	109.5
H11D—C110—H11F	109.5
Cl12—Hg1—Cl11—Hg1^i	−62.14 (10)	Cl12—Hg1—Cl22—Hg2	−11.92 (2)
N11—Hg1—Cl11—Hg1^i	135.17 (4)	N11—Hg1—Cl22—Hg2	−104.42 (5)
O12—Hg1—Cl11—Hg1^i	82.29 (4)	O12—Hg1—Cl22—Hg2	−107.65 (13)
Cl11^i—Hg1—Cl11—Hg1^i	0	Cl11^i—Hg1—Cl22—Hg2	72.84 (2)
Cl22—Hg1—Cl11—Hg1^i	−115.320 (17)	Hg1^i—Hg1—Cl22—Hg2	110.700 (16)
Cl11—Hg1—Cl12—Hg2	−44.45 (10)	Cl21—Hg2—S21—O22	−10.81 (10)
N11—Hg1—Cl12—Hg2	118.34 (4)	Cl22—Hg2—S21—O22	−177.96 (10)
O12—Hg1—Cl12—Hg2	171.39 (4)	N21—Hg2—S21—O22	88.54 (14)
Cl11^i—Hg1—Cl12—Hg2	−106.473 (17)	O21—Hg2—S21—O22	−99.04 (14)
Cl22—Hg1—Cl12—Hg2	9.074 (17)	Cl12—Hg2—S21—O22	87.74 (10)
Hg1^i—Hg1—Cl12—Hg2	−98.881 (16)	Cl21—Hg2—S21—O21	88.23 (9)
O11—S11—O12—Hg1	−126.27 (10)	Cl22—Hg2—S21—O21	−78.92 (9)
N11—S11—O12—Hg1	1.89 (10)	N21—Hg2—S21—O21	−172.42 (13)
C14—S11—O12—Hg1	115.65 (9)	Cl12—Hg2—S21—O21	−173.21 (9)
Cl11—Hg1—O12—S11	95.84 (8)	Cl21—Hg2—S21—N21	−99.35 (9)
Cl12—Hg1—O12—S11	−91.40 (8)	Cl22—Hg2—S21—N21	93.49 (9)
N11—Hg1—O12—S11	−1.47 (8)	O21—Hg2—S21—N21	172.42 (13)
Cl11^i—Hg1—O12—S11	−178.10 (9)	Cl12—Hg2—S21—N21	−0.80 (9)
Cl22—Hg1—O12—S11	2.3 (2)	Cl21—Hg2—S21—C24	175.16 (9)
Hg1^i—Hg1—O12—S11	146.11 (9)	Cl22—Hg2—S21—C24	8.01 (9)
O11—S11—N11—N12	−28.0 (2)	N21—Hg2—S21—C24	−85.49 (13)
O12—S11—N11—N12	−157.36 (17)	O21—Hg2—S21—C24	86.93 (13)
C14—S11—N11—N12	91.83 (18)	Cl12—Hg2—S21—C24	−86.28 (9)
O11—S11—N11—Hg1	127.16 (10)	O22—S21—O21—Hg2	121.91 (10)
O12—S11—N11—Hg1	−2.21 (12)	N21—S21—O21—Hg2	−5.77 (10)
C14—S11—N11—Hg1	−113.02 (10)	C24—S21—O21—Hg2	−119.90 (9)
Cl11—Hg1—N11—N12	65.80 (17)	Cl21—Hg2—O21—S21	−94.67 (8)
Cl12—Hg1—N11—N12	−110.52 (17)	Cl22—Hg2—O21—S21	103.18 (8)
O12—Hg1—N11—N12	153.7 (2)	N21—Hg2—O21—S21	4.42 (8)
Cl11^i—Hg1—N11—N12	158.46 (13)	Cl12—Hg2—O21—S21	14.22 (19)
Cl22—Hg1—N11—N12	−25.06 (18)	O22—S21—N21—N22	27.3 (2)
Hg1^i—Hg1—N11—N12	110.32 (16)	O21—S21—N21—N22	156.35 (16)
Cl11—Hg1—N11—S11	−86.54 (9)	C24—S21—N21—N22	−92.00 (17)
Cl12—Hg1—N11—S11	97.14 (9)	Hg2—S21—N21—N22	149.8 (2)
O12—Hg1—N11—S11	1.38 (7)	O22—S21—N21—Hg2	−122.48 (10)
Cl11^i—Hg1—N11—S11	6.13 (14)	O21—S21—N21—Hg2	6.54 (11)
Cl22—Hg1—N11—S11	−177.39 (8)	C24—S21—N21—Hg2	118.19 (10)
Hg1^i—Hg1—N11—S11	−42.02 (12)	Cl21—Hg2—N21—N22	−60.55 (16)
S11—N11—N12—C12	−165.10 (17)	Cl22—Hg2—N21—N22	123.91 (16)
Hg1—N11—N12—C12	45.6 (2)	O21—Hg2—N21—N22	−149.73 (19)
S11—N11—N12—C13	78.0 (2)	Cl12—Hg2—N21—N22	33.78 (17)
Hg1—N11—N12—C13	−71.2 (2)	S21—Hg2—N21—N22	−145.6 (2)
S11—N11—N12—C11	−47.4 (2)	Cl21—Hg2—N21—S21	85.07 (8)
Hg1—N11—N12—C11	163.34 (16)	Cl22—Hg2—N21—S21	−90.46 (8)
O11—S11—C14—C15	−38.7 (2)	O21—Hg2—N21—S21	−4.11 (7)
O12—S11—C14—C15	86.3 (2)	Cl12—Hg2—N21—S21	179.40 (7)
N11—S11—C14—C15	−163.77 (19)	S21—N21—N22—C23	163.75 (17)
O11—S11—C14—C19	146.38 (19)	Hg2—N21—N22—C23	−54.8 (2)
O12—S11—C14—C19	−88.6 (2)	S21—N21—N22—C22	46.8 (2)
N11—S11—C14—C19	21.3 (2)	Hg2—N21—N22—C22	−171.79 (15)
C19—C14—C15—C16	2.5 (4)	S21—N21—N22—C21	−79.1 (2)
S11—C14—C15—C16	−172.4 (2)	Hg2—N21—N22—C21	62.3 (2)
C14—C15—C16—C17	−0.9 (4)	O22—S21—C24—C29	33.0 (2)
C15—C16—C17—C18	−1.4 (4)	O21—S21—C24—C29	−91.9 (2)
C15—C16—C17—C110	176.9 (3)	N21—S21—C24—C29	157.19 (19)
C16—C17—C18—C19	2.2 (4)	Hg2—S21—C24—C29	−151.79 (16)
C110—C17—C18—C19	−176.2 (3)	O22—S21—C24—C25	−153.03 (19)
C17—C18—C19—C14	−0.6 (4)	O21—S21—C24—C25	82.1 (2)
C15—C14—C19—C18	−1.8 (4)	N21—S21—C24—C25	−28.8 (2)
S11—C14—C19—C18	173.02 (19)	Hg2—S21—C24—C25	22.2 (2)
Hg1—Cl12—Hg2—Cl21	−173.25 (2)	C29—C24—C25—C26	1.7 (4)
Hg1—Cl12—Hg2—Cl22	−12.50 (2)	S21—C24—C25—C26	−172.16 (18)
Hg1—Cl12—Hg2—N21	85.41 (5)	C24—C25—C26—C27	0.1 (4)
Hg1—Cl12—Hg2—O21	77.16 (12)	C25—C26—C27—C28	−2.0 (4)
Hg1—Cl12—Hg2—S21	85.81 (2)	C25—C26—C27—C210	176.1 (2)
Cl21—Hg2—Cl22—Hg1	97.01 (7)	C26—C27—C28—C29	2.1 (4)
N21—Hg2—Cl22—Hg1	−96.40 (5)	C210—C27—C28—C29	−175.9 (2)
O21—Hg2—Cl22—Hg1	−150.68 (4)	C25—C24—C29—C28	−1.5 (4)
Cl12—Hg2—Cl22—Hg1	9.031 (17)	S21—C24—C29—C28	172.3 (2)
S21—Hg2—Cl22—Hg1	−125.002 (15)	C27—C28—C29—C24	−0.4 (4)
Cl11—Hg1—Cl22—Hg2	158.12 (2)

Symmetry code: (i) −x, −y, −z.