(Dicyclohexyldithiophosphinato-S,S')[2-(2-pyridyl-N)­phenyl]­mercury(II)

The crystal structure of the title compound, [Hg(C₁₁H₈N)(C₁₂H₂₂PS₂)], consists of mol­ecules in which the Hg atom is coordinated strongly to the C atom in position 2 of the phenyl group and to one of the di­thio­phosphinate S atoms, and at longer distances to the pyridine N atom and the other S atom. The C-Hg-S fragment involving the S atom more strongly bound to Hg is almost linear [C-Hg-S = 178.9 (3)°].

S1. Comment

In the reaction of [2-(pyridin-2-yl)phenyl]mercury(II) acetate, [Hg(PhPy)(OAc)], with diphenyldithiophosphinic acid, HS₂PPh₂, the C—Hg bond is broken to afford phenylpyridine and [Hg₂(S₂PPh₂)₄] (Casas et al., 1997). The reaction of dicyclohexyldithiophosphinic acid, HS₂PCy₂, with an appropriate mole ratio of TlPh₂⁺ cation in chloroform likewise produces protodemetallation (i.e. the loss of one or more alkyl or aryl groups from the metal with formation of an alkane or arene), affording Tl³⁺ species and benzene (Casas et al., 1995). To explore this type of process further, we reacted [Hg(PhPy)(OAc)] with HS₂PCy₂. At room temperature the reaction afforded a black solid which probably contains HgS but at near 273 K, in an ice bath, it yielded a product from which colourless crystals of the title organomercury dithiophosphinato, [Hg(PhPy)(S₂PCy₂)], (I), were isolated, showing that no protodemetallation process had occurred. \scheme

Fig. 1 shows the molecular structure of (I) as drawn by ZORTEP (Zsolnai & Huttner, 1994), and the atom-numbering scheme used. Selected interatomic distances and angles are listed in Table 1. The Hg atom is strongly coordinated to C8, the carbon at position 2 of the phenyl group [Hg—C8 = 2.088 (11) Å], and to one of the dithiophosphinate sulfur atoms (S1). The C8—Hg—S1 fragment is almost linear [178.9 (3)°], as is usual in monoorganomercuric thiolate derivatives (Casas et al., 1999). The Hg—S1 distance [2.365 (3) Å] lies in the range observed for other organomercury(II) dithiophosphates and dithiophosphinates (Zukerman-Schpector et al., 1991; Vázquez-López et al., 1992; Casas et al., 1994). The Hg—N distance of 2.694 (9) Å is also shorter than the sum of the Van der Waals radii (3.55 Å; Casas et al., 1999; Bondi, 1964); it is close to the values found in [Hg(PhPy)Cl] [2.63 (1) and 2.67 (1) Å; Constable et al., 1989], but is clearly shorter than in [Hg(PhPy)(AcO)] [2.727 (9) Å; Casas et al., 1996] and longer than in [Hg(PhPy)(Hstsc)] [2.576 (6) Å; H₂stsc = 2-formyl-(2-hydroxy-benzene)thiosemicarbazone; Lobana et al., 1998]. The phenyl and pyridinyl rings of the [Hg(PhPy)]⁺ moiety in (I) are not coplanar but form a dihedral angle of 19.3 (6)°, and the interplanar angle is narrower than in the acetate derivative (Casas et al., 1996).

The other dithiophosphinato sulfur, S2, lies 3.336 (3) Å from the Hg atom. This distance, too, is shorter than the sum of the corresponding van der Waals radii (3.8 Å; Casas et al., 1999; Bondi, 1964), and though longer than that observed in [HgPh (S₂PEt₂)] [3.182 (3) Å; Casas et al., 1994], is within the usual range for secondary Hg···S bonds in monoorganomercury dithiophosphates and dithiophosphinates. Taking this Hg···S interaction into account, the coordination geometry around the Hg atom can be described as of a distorted square planar kind [the largest displacement from the least squares plane through Hg/N/C8/S1/S2 is for N, which is 0.35 (1) Å out of it].

Secondary Hg···S bonds in monoorganomercury dithiophosphates and dithiophosphinates are generally intermolecular, organizing the molecules into centrosymmetric dimers, as in [HgMe(S₂PPh₂)] (Zukerman-Schpector et al., 1991) and [HgPh{S₂P(OEt)₂}] (Vázquez-López et al., 1992), or in linear chains of identically oriented monomers, as in [HgPh(S₂PEt₂)]. In the case of (I), these possibilities are probably prevented by steric hindrance. The structure of this compound is probably most similar to that of the 2-formyl-(2-hydroxybenzene)thiosemicarbazonate, [Hg(PhPy)(Hstsc)] (Lobana et al., 1998). The lattices of these compounds consist of molecules which have no intermolecular interactions and in which the Hg atom has two primary bonds [Hg—C8, Hg—S1 and C8—Hg—S1 in the dithiophosphinate complex, (I) (Table 1); Hg—C = 2.083 (7) and Hg—S = 2.357 Å, and C—Hg—S = 177.7 (2)° in the thiosemicarbazonate] and two secondary bonds [Hg—N and Hg—S2 in (I) (Table 1); two Hg—N bonds with distances 2.576 (6) and 3.126 (6) Å in the thiosemicarbazonate]. Finally, the S₂PCy₂⁻ ligand is more anisobidentate in (I) (see Table 1) than in [TlPh₂(S₂PCy₂)] [Tl—S1 = 2.789 (3) and Tl—S2 = 2.816 (3) Å; Casas et al., 1995]. In keeping with this, the P—S1 bond, corresponding to S strongly coordinated to metal, is longer and the P—S2 bond shorter in (I) (Δ/σ = 18.2) than in the latter compound.

S2. Experimental

[2-(Pyridin-2-yl)phenyl]mercury acetate (21.6 mg, 0.052 mmol) and dicyclohexyldithiophosphinic acid (13.7 mg, 0.052 mmol) were dissolved in chloroform at 273 K. Slow evaporation in the refrigerator gave colourless crystals suitable for X-ray analysis.

S3. Refinement

Please provide details of H-atom refinement.

Computing details

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: Please specify; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: Please specify.

Figures

Fig. 1. Compound (I) (ZORTEP; Zsolnai & Huttner, 1994), showing the atom-numbering system. Displacement ellipsoids are drawn at 30% probability level and H atoms are shown as spheres of arbitrary radii.

(Dicyclohexyldithiophosphinato-S,S')-[2-(2-pyridyl-N)phenyl]mercury(II)

Crystal data

[Hg(C11H8N)(C12H22PS2)]	F(000) = 1208
Mr = 616.16	Dx = 1.758 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.923 (2) Å	Cell parameters from 25 reflections
b = 9.9557 (10) Å	θ = 8–15°
c = 15.728 (2) Å	µ = 6.87 mm^−1
β = 95.088 (10)°	T = 293 K
V = 2327.5 (5) Å^3	Block, colourless
Z = 4	0.25 × 0.25 × 0.15 mm

Data collection

Enraf Nonius CAD4 diffractometer	2272 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.060
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
non–profiled ω/2θ scans	h = −17→17
Absorption correction: analytical (Alcock, 1970)	k = 0→11
Tmin = 0.428, Tmax = 0.709	l = 0→18
4252 measured reflections	1 standard reflections every 30 min
4094 independent reflections	intensity decay: −3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Calculated w = 1/[σ^2(Fo^2) + (0.0266P)^2] where P = (Fo^2 + 2Fc^2)/3
4094 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.72 e Å^−3

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.

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 > σ(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. The structure was solved by direct methods, followed by usual difference Fourier techniques and refinement (on F²) by full-matrix least squares with unit weights and anisotropic displacement parameters for non-H atoms (Sheldrick, 1997).

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

	x	y	z	Uiso*/Ueq
Hg	−0.12353 (3)	0.44555 (4)	0.63039 (2)	0.04210 (13)
P	−0.09353 (18)	0.2849 (3)	0.81997 (15)	0.0336 (6)
S2	0.00580 (19)	0.4126 (3)	0.81338 (18)	0.0466 (7)
S1	−0.1802 (2)	0.2686 (3)	0.71043 (16)	0.0433 (7)
N	−0.2159 (7)	0.4408 (11)	0.4753 (5)	0.055 (2)
C2	−0.2693 (9)	0.3463 (13)	0.4371 (7)	0.062 (3)
H2	−0.3024	0.2916	0.4706	0.074*
C3	−0.2772 (8)	0.3268 (15)	0.3495 (8)	0.068 (4)
H3	−0.3150	0.2608	0.3245	0.082*
C4	−0.2283 (9)	0.4067 (15)	0.3013 (8)	0.072 (4)
H4	−0.2318	0.3950	0.2425	0.087*
C5	−0.1738 (8)	0.5045 (15)	0.3388 (7)	0.064 (4)
H5	−0.1421	0.5618	0.3056	0.077*
C6	−0.1663 (7)	0.5172 (10)	0.4274 (6)	0.042 (3)
C7	−0.1046 (7)	0.6159 (11)	0.4725 (7)	0.046 (3)
C12	−0.0684 (9)	0.7200 (14)	0.4275 (8)	0.062 (4)
H12	−0.0858	0.7288	0.3695	0.074*
C11	−0.0080 (9)	0.8102 (12)	0.4658 (8)	0.063 (4)
H11	0.0134	0.8803	0.4341	0.076*
C10	0.0210 (9)	0.7969 (13)	0.5511 (8)	0.063 (4)
H10	0.0623	0.8573	0.5773	0.075*
C9	−0.0128 (7)	0.6904 (11)	0.5979 (7)	0.049 (3)
H9	0.0077	0.6787	0.6550	0.059*
C8	−0.0758 (8)	0.6038 (11)	0.5599 (7)	0.047 (3)
C111	−0.0545 (6)	0.1122 (9)	0.8426 (6)	0.032 (2)
H111	−0.0128	0.1170	0.8943	0.039*
C112	−0.1285 (7)	0.0148 (9)	0.8620 (7)	0.036 (2)
H11A	−0.1585	0.0481	0.9101	0.044*
H11B	−0.1727	0.0092	0.8131	0.044*
C113	−0.0908 (8)	−0.1227 (11)	0.8826 (7)	0.054 (3)
H11C	−0.1400	−0.1840	0.8904	0.065*
H11D	−0.0529	−0.1188	0.9359	0.065*
C114	−0.0367 (8)	−0.1764 (11)	0.8138 (8)	0.057 (3)
H11E	−0.0761	−0.1912	0.7622	0.068*
H11F	−0.0104	−0.2621	0.8317	0.068*
C115	0.0371 (8)	−0.0802 (12)	0.7950 (8)	0.058 (3)
H11G	0.0684	−0.1151	0.7483	0.069*
H11H	0.0801	−0.0733	0.8448	0.069*
C116	0.0001 (7)	0.0591 (11)	0.7715 (6)	0.043 (3)
H11I	−0.0379	0.0544	0.7183	0.052*
H11J	0.0495	0.1199	0.7635	0.052*
C121	−0.1666 (6)	0.3264 (9)	0.9048 (5)	0.030 (2)
H121	−0.2159	0.2611	0.9016	0.036*
C122	−0.1162 (7)	0.3148 (11)	0.9930 (5)	0.040 (3)
H12A	−0.0661	0.3773	0.9976	0.048*
H12B	−0.0923	0.2247	1.0011	0.048*
C123	−0.1801 (8)	0.3462 (12)	1.0632 (6)	0.052 (3)
H12C	−0.2257	0.2768	1.0631	0.063*
H12D	−0.1460	0.3456	1.1186	0.063*
C124	−0.2245 (9)	0.4795 (12)	1.0490 (7)	0.060 (3)
H12E	−0.1794	0.5496	1.0569	0.072*
H12F	−0.2672	0.4925	1.0913	0.072*
C125	−0.2741 (8)	0.4927 (13)	0.9591 (7)	0.058 (3)
H12G	−0.3233	0.4289	0.9525	0.069*
H12H	−0.2988	0.5824	0.9513	0.069*
C126	−0.2075 (7)	0.4652 (11)	0.8918 (6)	0.048 (3)
H12I	−0.2386	0.4714	0.8351	0.057*
H12J	−0.1602	0.5323	0.8964	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg	0.0508 (2)	0.0434 (2)	0.0326 (2)	0.0071 (3)	0.00657 (16)	0.0083 (2)
P	0.0383 (15)	0.0327 (14)	0.0298 (13)	0.0016 (13)	0.0021 (11)	0.0042 (11)
S2	0.0465 (16)	0.0410 (18)	0.0534 (16)	−0.0112 (13)	0.0104 (13)	0.0034 (13)
S1	0.0473 (17)	0.0469 (17)	0.0339 (13)	−0.0053 (13)	−0.0058 (12)	0.0060 (12)
N	0.072 (6)	0.054 (6)	0.040 (5)	−0.010 (6)	0.013 (5)	0.008 (5)
C2	0.090 (10)	0.056 (8)	0.039 (6)	−0.005 (8)	0.004 (6)	0.007 (6)
C3	0.056 (8)	0.086 (11)	0.060 (8)	−0.002 (8)	−0.008 (7)	0.005 (8)
C4	0.075 (9)	0.103 (13)	0.040 (7)	0.004 (9)	0.007 (7)	0.003 (7)
C5	0.058 (8)	0.094 (11)	0.042 (7)	0.002 (7)	0.019 (6)	0.009 (7)
C6	0.051 (7)	0.038 (7)	0.039 (6)	0.023 (5)	0.018 (5)	0.010 (5)
C7	0.048 (7)	0.043 (7)	0.047 (6)	0.008 (6)	0.017 (5)	0.006 (5)
C12	0.070 (9)	0.070 (9)	0.049 (7)	0.009 (8)	0.024 (7)	0.031 (7)
C11	0.076 (9)	0.045 (8)	0.074 (9)	−0.001 (7)	0.035 (8)	0.010 (7)
C10	0.074 (9)	0.045 (8)	0.072 (9)	0.001 (7)	0.021 (7)	0.005 (7)
C9	0.041 (6)	0.052 (8)	0.054 (7)	0.012 (6)	0.005 (5)	0.003 (6)
C8	0.053 (7)	0.045 (7)	0.044 (6)	0.006 (6)	0.016 (5)	0.003 (5)
C111	0.040 (6)	0.024 (5)	0.032 (5)	0.009 (4)	−0.001 (4)	0.000 (4)
C112	0.043 (6)	0.019 (5)	0.047 (6)	−0.008 (4)	0.003 (5)	0.007 (4)
C113	0.060 (8)	0.039 (7)	0.062 (7)	0.002 (6)	0.004 (6)	−0.003 (6)
C114	0.069 (8)	0.029 (7)	0.069 (8)	0.000 (6)	−0.011 (7)	0.000 (6)
C115	0.056 (7)	0.058 (9)	0.062 (7)	0.026 (7)	0.017 (6)	−0.010 (6)
C116	0.055 (6)	0.034 (6)	0.044 (6)	0.004 (6)	0.020 (5)	−0.003 (6)
C121	0.038 (5)	0.025 (5)	0.026 (5)	−0.001 (4)	0.002 (4)	0.003 (4)
C122	0.052 (6)	0.044 (7)	0.023 (5)	0.004 (5)	0.001 (4)	0.002 (5)
C123	0.065 (8)	0.062 (8)	0.033 (5)	0.006 (7)	0.017 (5)	0.004 (6)
C124	0.074 (9)	0.051 (9)	0.055 (7)	0.019 (7)	0.011 (7)	−0.003 (6)
C125	0.063 (8)	0.058 (8)	0.052 (7)	0.020 (6)	0.005 (6)	0.004 (6)
C126	0.059 (7)	0.047 (8)	0.038 (5)	0.010 (6)	0.005 (5)	0.009 (5)

Geometric parameters (Å, º)

Hg—C8	2.088 (11)	C7—C12	1.391 (15)
Hg—S1	2.365 (3)	C7—C8	1.407 (15)
Hg—N	2.694 (9)	C12—C11	1.373 (17)
Hg—S2	3.336 (3)	C11—C10	1.379 (17)
Hg—C12^i	3.495 (12)	C10—C9	1.410 (15)
Hg—C11^i	3.626 (11)	C9—C8	1.374 (15)
Hg—C7^i	3.945 (10)	C111—C112	1.521 (13)
P—C111	1.839 (9)	C111—C116	1.535 (12)
P—C121	1.843 (8)	C112—C113	1.505 (13)
P—S2	1.963 (4)	C113—C114	1.505 (15)
P—S1	2.066 (4)	C114—C115	1.508 (15)
N—C6	1.338 (13)	C115—C116	1.525 (14)
N—C2	1.342 (15)	C121—C126	1.518 (13)
C2—C3	1.385 (15)	C121—C122	1.522 (12)
C3—C4	1.355 (17)	C122—C123	1.553 (12)
C4—C5	1.369 (17)	C123—C124	1.491 (15)
C5—C6	1.393 (14)	C124—C125	1.542 (15)
C6—C7	1.484 (15)	C125—C126	1.538 (13)
C8—Hg—S1	178.9 (3)	C4—C3—C2	118.1 (14)
C8—Hg—N	72.7 (4)	C3—C4—C5	120.4 (12)
S1—Hg—N	106.9 (2)	C4—C5—C6	119.2 (12)
C8—Hg—S2	109.5 (3)	N—C6—C5	120.8 (12)
S1—Hg—S2	70.99 (8)	N—C6—C7	117.2 (9)
N—Hg—S2	171.8 (2)	C5—C6—C7	122.0 (10)
C8—Hg—C12^i	83.8 (3)	C12—C7—C8	117.5 (11)
S1—Hg—C12^i	97.3 (2)	C12—C7—C6	120.1 (10)
N—Hg—C12^i	96.9 (3)	C8—C7—C6	122.2 (10)
S2—Hg—C12^i	75.7 (2)	C11—C12—C7	122.3 (12)
C8—Hg—C11^i	94.9 (3)	C12—C11—C10	120.1 (12)
S1—Hg—C11^i	86.0 (2)	C11—C10—C9	119.0 (13)
N—Hg—C11^i	82.1 (3)	C8—C9—C10	120.5 (11)
S2—Hg—C11^i	89.9 (2)	C9—C8—C7	120.6 (10)
C12^i—Hg—C11^i	22.1 (3)	C9—C8—Hg	119.7 (8)
C8—Hg—C7^i	63.3 (3)	C7—C8—Hg	119.6 (9)
S1—Hg—C7^i	117.71 (17)	C112—C111—C116	111.6 (8)
N—Hg—C7^i	90.9 (3)	C112—C111—P	114.3 (7)
S2—Hg—C7^i	83.37 (17)	C116—C111—P	111.1 (7)
C12^i—Hg—C7^i	20.4 (2)	C113—C112—C111	111.0 (8)
C11^i—Hg—C7^i	37.0 (3)	C112—C113—C114	112.5 (10)
C111—P—C121	105.5 (4)	C113—C114—C115	111.3 (10)
C111—P—S2	112.8 (3)	C114—C115—C116	111.7 (9)
C121—P—S2	113.0 (3)	C115—C116—C111	109.9 (8)
C111—P—S1	104.6 (3)	C126—C121—C122	110.6 (8)
C121—P—S1	104.8 (3)	C126—C121—P	111.3 (6)
S2—P—S1	115.24 (17)	C122—C121—P	111.5 (6)
P—S2—Hg	74.18 (11)	C121—C122—C123	110.4 (8)
P—S1—Hg	99.12 (13)	C124—C123—C122	111.5 (9)
C6—N—C2	118.9 (9)	C123—C124—C125	112.6 (10)
C6—N—Hg	103.6 (7)	C126—C125—C124	109.2 (9)
C2—N—Hg	130.9 (7)	C121—C126—C125	110.3 (8)
N—C2—C3	122.6 (12)
C111—P—S2—Hg	125.4 (3)	C12—C11—C10—C9	−0.4 (18)
C121—P—S2—Hg	−115.1 (3)	C11—C10—C9—C8	−2.0 (17)
S1—P—S2—Hg	5.35 (15)	C10—C9—C8—C7	3.0 (16)
C8—Hg—S2—P	174.5 (3)	C10—C9—C8—Hg	179.3 (8)
S1—Hg—S2—P	−4.47 (12)	C12—C7—C8—C9	−1.4 (16)
N—Hg—S2—P	−80.9 (14)	C6—C7—C8—C9	174.5 (9)
C12^i—Hg—S2—P	−107.6 (2)	C12—C7—C8—Hg	−177.7 (8)
C11^i—Hg—S2—P	−90.3 (2)	C6—C7—C8—Hg	−1.8 (13)
C7^i—Hg—S2—P	−126.8 (2)	S1—Hg—C8—C9	105 (17)
C111—P—S1—Hg	−131.8 (3)	N—Hg—C8—C9	176.1 (9)
C121—P—S1—Hg	117.5 (3)	S2—Hg—C8—C9	−12.1 (9)
S2—P—S1—Hg	−7.4 (2)	C12^i—Hg—C8—C9	−84.6 (9)
C8—Hg—S1—P	−113 (17)	C11^i—Hg—C8—C9	−103.7 (9)
N—Hg—S1—P	175.9 (2)	C7^i—Hg—C8—C9	−83.8 (9)
S2—Hg—S1—P	4.14 (12)	S1—Hg—C8—C7	−79 (17)
C12^i—Hg—S1—P	76.3 (3)	N—Hg—C8—C7	−7.5 (8)
C11^i—Hg—S1—P	95.4 (3)	S2—Hg—C8—C7	164.2 (7)
C7^i—Hg—S1—P	75.5 (2)	C12^i—Hg—C8—C7	91.8 (8)
C8—Hg—N—C6	16.6 (7)	C11^i—Hg—C8—C7	72.6 (9)
S1—Hg—N—C6	−164.4 (6)	C7^i—Hg—C8—C7	92.6 (8)
S2—Hg—N—C6	−90.6 (16)	C121—P—C111—C112	47.0 (8)
C12^i—Hg—N—C6	−64.6 (7)	S2—P—C111—C112	170.8 (6)
C11^i—Hg—N—C6	−81.1 (7)	S1—P—C111—C112	−63.2 (7)
C7^i—Hg—N—C6	−45.0 (7)	C121—P—C111—C116	174.5 (7)
C8—Hg—N—C2	166.8 (11)	S2—P—C111—C116	−61.7 (8)
S1—Hg—N—C2	−14.3 (11)	S1—P—C111—C116	64.3 (7)
S2—Hg—N—C2	59.5 (19)	C116—C111—C112—C113	54.7 (11)
C12^i—Hg—N—C2	85.6 (11)	P—C111—C112—C113	−178.2 (7)
C11^i—Hg—N—C2	69.1 (11)	C111—C112—C113—C114	−54.5 (12)
C7^i—Hg—N—C2	105.1 (11)	C112—C113—C114—C115	55.0 (13)
C6—N—C2—C3	−1.8 (19)	C113—C114—C115—C116	−55.7 (13)
Hg—N—C2—C3	−148.3 (10)	C114—C115—C116—C111	55.6 (12)
N—C2—C3—C4	0 (2)	C112—C111—C116—C115	−55.1 (12)
C2—C3—C4—C5	−1 (2)	P—C111—C116—C115	176.1 (7)
C3—C4—C5—C6	3 (2)	C111—P—C121—C126	−177.4 (7)
C2—N—C6—C5	3.7 (17)	S2—P—C121—C126	59.0 (8)
Hg—N—C6—C5	158.3 (9)	S1—P—C121—C126	−67.3 (7)
C2—N—C6—C7	−177.0 (10)	C111—P—C121—C122	58.6 (8)
Hg—N—C6—C7	−22.4 (10)	S2—P—C121—C122	−65.1 (7)
C4—C5—C6—N	−4.2 (18)	S1—P—C121—C122	168.7 (6)
C4—C5—C6—C7	176.5 (11)	C126—C121—C122—C123	57.2 (11)
N—C6—C7—C12	−163.9 (10)	P—C121—C122—C123	−178.3 (7)
C5—C6—C7—C12	15.4 (16)	C121—C122—C123—C124	−54.4 (13)
N—C6—C7—C8	20.3 (15)	C122—C123—C124—C125	54.4 (14)
C5—C6—C7—C8	−160.4 (11)	C123—C124—C125—C126	−56.0 (14)
C8—C7—C12—C11	−1.1 (18)	C122—C121—C126—C125	−60.1 (11)
C6—C7—C12—C11	−177.1 (11)	P—C121—C126—C125	175.4 (7)
C7—C12—C11—C10	2 (2)	C124—C125—C126—C121	58.0 (13)

Symmetry code: (i) −x, −y+1, −z+1.