Bis[N-(4-nitro­phen­yl)thio­benz­amidato]­mercury(II)

The mol­ecule of the title compound, [Hg(C₁₃H₉N₂O₂S)₂], has approximate twofold rotation symmetry, with the Hg atom in an essentially linear two-coordinate HgS₂ environment supported by secondary π inter­actions with the nitro­phenyl rings of both ligands. The ligands are in the imine–thiol­ate rather than the amine–thione tautomeric form.

S1. Comment

The fact that mercury(II) ions interact with many biological molecules through coordination with deprotonated thiol, imidazole, disulfide, thioether, amino or carboxylate groups is well known, and a great deal of effort has been devoted to the characterization of these interactions in model molecules and in proteins (Popovic et al., 2000; Kajdan et al., 2000). Interest in the structural chemistry of mercury(II) complexes with ligands containing S-donor atoms, such as thioamides, is related not only to the toxicological behaviour of the metal and to the detoxification of mercury, but also to their industrial applications, especially in semiconductors or in photovoltaic devices (Hadjikakou et al., 2003). Consequently, a number of attempts have been made to explore the coordination chemistry of mercury(II) with diverse sulfur-containing ligands, such as aromatic thiolates (Bell, Branston et al., 2001; Bell, Coles et al., 2001; Bell et al., 2004; Blower & Dilworth, 1987). Extensive use of thionates as bridging ligands stems from the presence of the thioamide NCS group. Parent ligands adopt the thione form in the solid but may exist, at least in part, as the thiol form in solution, particularly in non-polar solvents (Cotton & Walton, 1993). This work describes the synthesis and crystal structure of a mercury(II) complex of such a ligand, the title compound, (I), which is only the second example to be crystallographically characterized.

The molecular structure of (I) is shown in Fig. 1. The molecule has no crystallographic symmetry, but the molecular symmetry is close to C₂, with approximately linear coordination of Hg. The Hg—S distances (Table 1) agree well with those in similar mercury(II) complexes, e.g. 2.344 (3)–2.351 (3) Å (Bell, Coles et al., 2001) and 2.338 (3)–2.345 (3) Å (Popovic et al., 2002); the mean value for Hg—S distances in Hg^II arenethionate complexes in the compilation of Orpen et al. (1989) is 2.362 Å. The S—C distances are indicative of single bonds, also in reasonable agreement with the mean value of 1.761 Å reported for related systems by Orpen et al. (1989).

The phenyl and nitrophenyl rings make dihedral angles of 19.2 (2) and 68.51 (8)°, respectively, with the SC(N)C thionate unit in the S1 ligand, and the corresponding angles in the S2 ligand are 40.71 (15) and 75.21 (9)°. The dihedral angles between the two aromatic rings within each ligand are 86.75 (12) and 65.28 (12)°, and the nitro group is essentially coplanar with its parent benzene ring in each case, with dihedral angles of 3.0 (2) and 8.3 (3)°. The C—S···S···C pseudo-torsion angle indicating the relative twist of the two ligands in their coordination of Hg is 70.5 (2)°.

The most closely related previous mercury(II) complex to be crystallographically characterized has two thioacetanilide ligands (Avalos et al., 1997). It is much less symmetrical, having a weak π coordination of the phenyl ring of one ligand to Hg, while the other is oriented well away from the metal. In the title complex, both nitrophenyl groups lie in orientations such that the shortest Hg···C distance is close to 3 Å [Hg1···C8 = 2.979 (4) and Hg1···C21 = 3.008 (4) Å] and this Hg···C vector is approximately perpendicular to the ring. The most significant intermolecular interactions include a short S2···O4(1/2 − x, 1/2 + y, 3/2 − z) contact of 3.050 (4) Å, some C—H···π interactions with H···ring-centroid distances < 3 Å, and a slipped π-stacking interaction between centrosymmetrically related nitrophenyl rings (C21–C26), with a centroid-to-centroid distance of 3.906 (2) Å and a perpendicular interplanar distance of 3.466 Å, the lateral slippage being 1.802 Å.

S2. Experimental

Mercury(II) oxide (0.216 g, 1 mmol) was added to a solution of N-(2-methylphenyl) 4-nitrothiobenzamide (0.273 g, 1 mmol) at ambient temperature in chloroform (35 ml) and stirred for 130 min. The completion of the reaction was followed by thin-layer chromatography with CCl₄–CH₃OH (15:1 v/v) as eluent. The mixture was filtered through Celite to remove unreacted mercury(II) compounds. The pale-yellow crystals which formed by slow evaporation were separated, recrystallized from chloroform as fine pale-yellow crystals and dried in vacuo (yield 95%, m.p. 466–468 K). Analysis, calculated for C₂₆H₁₈N₄O₄S₂Hg: C 45.28, H 2.96, N 7.55, Hg 26.95%; found: C 45.12, H 3.12, N 7.35, Hg 27.08%.

S3. Refinement

All H atoms were located in a difference map, idealized and treated as riding, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). The crystal was a non-merohedral twin and the overlap of inequivalent reflections was treated by ROTWIN (Pink & Young, 2000). The largest residual difference electron-density features lie 1.0–1.3 Å from Hg.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2005); program(s) used to refine structure: SHELXTL (Sheldrick, 2005); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: SHELXTL (Sheldrick, 2005) and local programs.

Figures

Fig. 1. The molecular structure of (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Bis[N-(4-nitrophenyl)thiobenzamidato]mercury(II)

Crystal data

[Hg(C13H9N2O2S)2]	F(000) = 1384
Mr = 715.15	Dx = 1.906 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 204 reflections
a = 9.7351 (8) Å	θ = 2.5–27.5°
b = 14.3655 (14) Å	µ = 6.39 mm^−1
c = 17.9804 (12) Å	T = 150 K
β = 97.648 (6)°	Needle, pale yellow
V = 2492.2 (4) Å^3	0.57 × 0.19 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	4332 independent reflections
Radiation source: sealed tube	3779 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ϕ and ω scans	θmax = 25.1°, θmin = 4.5°
Absorption correction: numerical (SHELXTL; Sheldrick, 2005)	h = −11→11
Tmin = 0.088, Tmax = 0.414	k = −17→17
27468 measured reflections	l = −21→21

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.054	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0152P)^2 + 3.6857P] where P = (Fo^2 + 2Fc^2)/3
4332 reflections	(Δ/σ)max = 0.003
337 parameters	Δρmax = 1.07 e Å^−3
0 restraints	Δρmin = −0.78 e Å^−3

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

	x	y	z	Uiso*/Ueq
Hg1	0.365692 (16)	0.553143 (12)	0.704857 (8)	0.02291 (6)
S1	0.45050 (11)	0.40043 (8)	0.71002 (6)	0.0262 (2)
C1	0.5596 (4)	0.3923 (3)	0.6390 (2)	0.0193 (9)
C2	0.5843 (4)	0.2943 (3)	0.6155 (2)	0.0204 (9)
C3	0.6984 (4)	0.2753 (3)	0.5782 (2)	0.0219 (9)
H3	0.7602	0.3241	0.5695	0.026*
C4	0.7224 (5)	0.1859 (3)	0.5536 (2)	0.0280 (10)
H4	0.8002	0.1739	0.5283	0.034*
C5	0.6340 (5)	0.1147 (3)	0.5658 (3)	0.0385 (12)
H5	0.6489	0.0539	0.5478	0.046*
C6	0.5231 (5)	0.1321 (3)	0.6046 (3)	0.0461 (14)
H6	0.4636	0.0825	0.6144	0.055*
C7	0.4979 (5)	0.2214 (3)	0.6293 (3)	0.0352 (11)
H7	0.4212	0.2325	0.6558	0.042*
C8	0.6172 (4)	0.5519 (3)	0.6269 (2)	0.0183 (8)
C9	0.5556 (4)	0.6170 (3)	0.5733 (2)	0.0223 (9)
H9	0.5099	0.5958	0.5264	0.027*
C10	0.5616 (4)	0.7109 (3)	0.5891 (2)	0.0234 (9)
H10	0.5192	0.7545	0.5535	0.028*
C11	0.6300 (4)	0.7410 (3)	0.6572 (2)	0.0194 (9)
C12	0.6925 (4)	0.6793 (3)	0.7108 (2)	0.0222 (9)
H12	0.7388	0.7017	0.7573	0.027*
C13	0.6861 (4)	0.5842 (3)	0.6956 (2)	0.0223 (9)
H13	0.7284	0.5412	0.7317	0.027*
N1	0.6190 (3)	0.4581 (2)	0.60686 (18)	0.0201 (7)
N2	0.6331 (4)	0.8405 (3)	0.6742 (2)	0.0262 (8)
O1	0.6957 (3)	0.8671 (2)	0.73455 (18)	0.0351 (8)
O2	0.5717 (4)	0.8940 (2)	0.6275 (2)	0.0427 (9)
S2	0.27669 (11)	0.70401 (8)	0.71190 (6)	0.0283 (3)
C14	0.1559 (4)	0.7195 (3)	0.6289 (2)	0.0232 (9)
C15	0.1133 (4)	0.8184 (3)	0.6176 (2)	0.0230 (9)
C16	−0.0266 (4)	0.8363 (3)	0.5934 (2)	0.0270 (10)
H16	−0.0899	0.7861	0.5837	0.032*
C17	−0.0730 (5)	0.9272 (3)	0.5837 (3)	0.0379 (12)
H17	−0.1685	0.9390	0.5680	0.045*
C18	0.0187 (5)	1.0010 (3)	0.5966 (3)	0.0359 (11)
H18	−0.0138	1.0632	0.5901	0.043*
C19	0.1571 (5)	0.9837 (3)	0.6188 (3)	0.0321 (11)
H19	0.2203	1.0342	0.6265	0.038*
C20	0.2054 (5)	0.8934 (3)	0.6303 (2)	0.0275 (10)
H20	0.3008	0.8823	0.6467	0.033*
C21	0.1093 (4)	0.5626 (3)	0.5915 (2)	0.0232 (9)
C22	0.1784 (4)	0.5074 (3)	0.5436 (2)	0.0255 (9)
H22	0.2284	0.5363	0.5079	0.031*
C23	0.1741 (5)	0.4113 (3)	0.5481 (2)	0.0277 (10)
H23	0.2208	0.3740	0.5158	0.033*
C24	0.1010 (4)	0.3701 (3)	0.6004 (2)	0.0268 (10)
C25	0.0322 (5)	0.4226 (3)	0.6485 (3)	0.0317 (11)
H25	−0.0178	0.3930	0.6838	0.038*
C26	0.0374 (4)	0.5180 (3)	0.6445 (3)	0.0292 (10)
H26	−0.0082	0.5544	0.6779	0.035*
N3	0.1004 (4)	0.6585 (3)	0.58198 (19)	0.0260 (8)
N4	0.0957 (4)	0.2685 (3)	0.6056 (2)	0.0377 (10)
O3	0.1700 (4)	0.2228 (3)	0.5688 (2)	0.0496 (10)
O4	0.0177 (4)	0.2327 (3)	0.6465 (2)	0.0488 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.02093 (9)	0.02133 (10)	0.02660 (10)	0.00489 (7)	0.00359 (6)	−0.00331 (7)
S1	0.0322 (6)	0.0198 (6)	0.0286 (6)	0.0066 (5)	0.0116 (4)	0.0046 (4)
C1	0.018 (2)	0.018 (2)	0.020 (2)	0.0030 (17)	−0.0028 (15)	−0.0008 (16)
C2	0.020 (2)	0.020 (2)	0.020 (2)	0.0021 (18)	−0.0007 (15)	0.0007 (16)
C3	0.025 (2)	0.018 (2)	0.021 (2)	0.0041 (18)	−0.0012 (16)	0.0013 (16)
C4	0.030 (2)	0.026 (3)	0.028 (2)	0.008 (2)	0.0027 (18)	−0.0015 (18)
C5	0.039 (3)	0.017 (3)	0.058 (3)	0.009 (2)	0.000 (2)	−0.011 (2)
C6	0.035 (3)	0.017 (3)	0.087 (4)	−0.006 (2)	0.013 (3)	−0.001 (3)
C7	0.029 (2)	0.017 (2)	0.061 (3)	0.001 (2)	0.013 (2)	0.002 (2)
C8	0.021 (2)	0.017 (2)	0.018 (2)	−0.0007 (17)	0.0057 (15)	−0.0015 (16)
C9	0.028 (2)	0.022 (2)	0.016 (2)	−0.0005 (18)	0.0000 (16)	−0.0035 (16)
C10	0.025 (2)	0.016 (2)	0.028 (2)	0.0024 (18)	0.0011 (17)	0.0021 (17)
C11	0.017 (2)	0.014 (2)	0.028 (2)	0.0005 (16)	0.0041 (16)	−0.0041 (16)
C12	0.021 (2)	0.021 (2)	0.022 (2)	−0.0018 (17)	−0.0021 (16)	−0.0082 (17)
C13	0.020 (2)	0.024 (2)	0.022 (2)	0.0024 (17)	0.0002 (16)	0.0021 (17)
N1	0.0242 (18)	0.0140 (19)	0.0222 (19)	0.0017 (14)	0.0034 (13)	−0.0017 (14)
N2	0.0250 (19)	0.0149 (19)	0.039 (2)	−0.0017 (16)	0.0055 (16)	−0.0031 (16)
O1	0.0412 (19)	0.0214 (18)	0.041 (2)	−0.0061 (14)	−0.0011 (14)	−0.0130 (14)
O2	0.048 (2)	0.0167 (18)	0.060 (2)	0.0031 (16)	−0.0056 (17)	−0.0002 (16)
S2	0.0291 (6)	0.0234 (6)	0.0307 (6)	0.0100 (5)	−0.0030 (4)	−0.0095 (4)
C14	0.020 (2)	0.027 (3)	0.024 (2)	0.0046 (18)	0.0051 (16)	−0.0012 (18)
C15	0.029 (2)	0.025 (2)	0.016 (2)	0.0065 (19)	0.0060 (16)	−0.0033 (17)
C16	0.029 (2)	0.023 (2)	0.028 (2)	0.001 (2)	−0.0001 (18)	0.0020 (18)
C17	0.036 (3)	0.033 (3)	0.043 (3)	0.011 (2)	−0.003 (2)	0.007 (2)
C18	0.054 (3)	0.021 (3)	0.034 (3)	0.004 (2)	0.008 (2)	0.005 (2)
C19	0.043 (3)	0.022 (2)	0.033 (3)	−0.006 (2)	0.013 (2)	−0.0033 (19)
C20	0.025 (2)	0.028 (3)	0.031 (3)	0.001 (2)	0.0089 (18)	−0.0052 (19)
C21	0.022 (2)	0.019 (2)	0.027 (2)	−0.0006 (18)	−0.0041 (16)	−0.0031 (17)
C22	0.029 (2)	0.028 (3)	0.020 (2)	−0.0011 (19)	0.0037 (17)	−0.0022 (18)
C23	0.031 (2)	0.024 (2)	0.027 (2)	0.0031 (19)	−0.0015 (18)	−0.0065 (18)
C24	0.026 (2)	0.016 (2)	0.035 (3)	−0.0016 (18)	−0.0101 (18)	0.0000 (18)
C25	0.029 (2)	0.033 (3)	0.033 (3)	−0.009 (2)	0.0042 (19)	0.003 (2)
C26	0.024 (2)	0.032 (3)	0.032 (3)	−0.001 (2)	0.0062 (18)	−0.0026 (19)
N3	0.030 (2)	0.019 (2)	0.029 (2)	0.0014 (16)	0.0004 (15)	−0.0040 (15)
N4	0.035 (2)	0.027 (2)	0.045 (3)	−0.003 (2)	−0.0199 (19)	−0.0037 (19)
O3	0.061 (2)	0.028 (2)	0.055 (2)	0.0067 (18)	−0.0110 (19)	−0.0059 (17)
O4	0.046 (2)	0.033 (2)	0.063 (3)	−0.0171 (17)	−0.0126 (18)	0.0139 (18)

Geometric parameters (Å, º)

Hg1—S1	2.3415 (11)	N2—O2	1.233 (5)
Hg1—S2	2.3438 (11)	S2—C14	1.787 (4)
S1—C1	1.770 (4)	C14—C15	1.486 (6)
C1—C2	1.499 (6)	C14—N3	1.284 (5)
C1—N1	1.285 (5)	C15—C16	1.397 (6)
C2—C3	1.399 (6)	C15—C20	1.400 (6)
C2—C7	1.386 (6)	C16—H16	0.950
C3—H3	0.950	C16—C17	1.386 (6)
C3—C4	1.388 (6)	C17—H17	0.950
C4—H4	0.950	C17—C18	1.385 (7)
C4—C5	1.373 (7)	C18—H18	0.950
C5—H5	0.950	C18—C19	1.377 (7)
C5—C6	1.383 (7)	C19—H19	0.950
C6—H6	0.950	C19—C20	1.386 (7)
C6—C7	1.390 (7)	C20—H20	0.950
C7—H7	0.950	C21—C22	1.406 (6)
C8—C9	1.418 (6)	C21—C26	1.410 (6)
C8—C13	1.403 (6)	C21—N3	1.390 (6)
C8—N1	1.395 (5)	C22—H22	0.950
C9—H9	0.950	C22—C23	1.384 (6)
C9—C10	1.377 (6)	C23—H23	0.950
C10—H10	0.950	C23—C24	1.385 (6)
C10—C11	1.382 (6)	C24—C25	1.384 (7)
C11—C12	1.389 (6)	C24—N4	1.464 (6)
C11—N2	1.462 (5)	C25—H25	0.950
C12—H12	0.950	C25—C26	1.374 (7)
C12—C13	1.393 (6)	C26—H26	0.950
C13—H13	0.950	N4—O3	1.233 (6)
N2—O1	1.232 (5)	N4—O4	1.237 (6)
S1—Hg1—S2	174.37 (4)	Hg1—S2—C14	106.10 (15)
Hg1—S1—C1	105.98 (14)	S2—C14—C15	112.0 (3)
S1—C1—C2	113.6 (3)	S2—C14—N3	129.5 (3)
S1—C1—N1	128.7 (3)	C15—C14—N3	118.5 (4)
C2—C1—N1	117.8 (4)	C14—C15—C16	117.5 (4)
C1—C2—C3	119.1 (4)	C14—C15—C20	123.5 (4)
C1—C2—C7	122.3 (4)	C16—C15—C20	119.1 (4)
C3—C2—C7	118.6 (4)	C15—C16—H16	120.0
C2—C3—H3	119.7	C15—C16—C17	120.1 (4)
C2—C3—C4	120.7 (4)	H16—C16—C17	120.0
H3—C3—C4	119.7	C16—C17—H17	119.7
C3—C4—H4	119.9	C16—C17—C18	120.5 (4)
C3—C4—C5	120.2 (4)	H17—C17—C18	119.7
H4—C4—C5	119.9	C17—C18—H18	120.2
C4—C5—H5	120.2	C17—C18—C19	119.6 (5)
C4—C5—C6	119.6 (4)	H18—C18—C19	120.2
H5—C5—C6	120.2	C18—C19—H19	119.6
C5—C6—H6	119.6	C18—C19—C20	120.8 (4)
C5—C6—C7	120.7 (5)	H19—C19—C20	119.6
H6—C6—C7	119.6	C15—C20—C19	119.9 (4)
C2—C7—C6	120.1 (4)	C15—C20—H20	120.1
C2—C7—H7	120.0	C19—C20—H20	120.1
C6—C7—H7	120.0	C22—C21—C26	118.6 (4)
C9—C8—C13	119.3 (4)	C22—C21—N3	120.8 (4)
C9—C8—N1	118.7 (3)	C26—C21—N3	120.3 (4)
C13—C8—N1	121.7 (4)	C21—C22—H22	119.8
C8—C9—H9	119.9	C21—C22—C23	120.4 (4)
C8—C9—C10	120.2 (4)	H22—C22—C23	119.8
H9—C9—C10	119.9	C22—C23—H23	120.4
C9—C10—H10	120.3	C22—C23—C24	119.2 (4)
C9—C10—C11	119.4 (4)	H23—C23—C24	120.4
H10—C10—C11	120.3	C23—C24—C25	121.8 (4)
C10—C11—C12	122.0 (4)	C23—C24—N4	119.7 (4)
C10—C11—N2	119.1 (4)	C25—C24—N4	118.6 (4)
C12—C11—N2	118.9 (4)	C24—C25—H25	120.5
C11—C12—H12	120.5	C24—C25—C26	119.1 (4)
C11—C12—C13	119.0 (4)	H25—C25—C26	120.5
H12—C12—C13	120.5	C21—C26—C25	121.0 (4)
C8—C13—C12	120.1 (4)	C21—C26—H26	119.5
C8—C13—H13	120.0	C25—C26—H26	119.5
C12—C13—H13	120.0	C14—N3—C21	125.6 (4)
C1—N1—C8	124.9 (3)	C24—N4—O3	117.9 (4)
C11—N2—O1	118.8 (4)	C24—N4—O4	118.9 (4)
C11—N2—O2	118.2 (4)	O3—N4—O4	123.2 (4)
O1—N2—O2	123.1 (4)
Hg1—S1—C1—C2	−160.0 (2)	Hg1—S2—C14—C15	−167.9 (2)
Hg1—S1—C1—N1	20.8 (4)	Hg1—S2—C14—N3	15.0 (4)
S1—C1—C2—C3	−160.6 (3)	S2—C14—C15—C16	−138.5 (3)
S1—C1—C2—C7	19.5 (5)	S2—C14—C15—C20	41.1 (5)
N1—C1—C2—C3	18.8 (5)	N3—C14—C15—C16	39.0 (5)
N1—C1—C2—C7	−161.2 (4)	N3—C14—C15—C20	−141.4 (4)
C1—C2—C3—C4	−178.1 (4)	C14—C15—C16—C17	178.4 (4)
C7—C2—C3—C4	1.8 (6)	C20—C15—C16—C17	−1.2 (6)
C2—C3—C4—C5	−0.1 (6)	C15—C16—C17—C18	1.0 (7)
C3—C4—C5—C6	−1.8 (7)	C16—C17—C18—C19	0.3 (7)
C4—C5—C6—C7	1.9 (8)	C17—C18—C19—C20	−1.6 (7)
C1—C2—C7—C6	178.2 (4)	C18—C19—C20—C15	1.4 (6)
C3—C2—C7—C6	−1.7 (7)	C14—C15—C20—C19	−179.6 (4)
C5—C6—C7—C2	−0.2 (8)	C16—C15—C20—C19	0.0 (6)
C13—C8—C9—C10	−0.9 (6)	C26—C21—C22—C23	0.8 (6)
N1—C8—C9—C10	−174.8 (4)	N3—C21—C22—C23	−173.0 (4)
C8—C9—C10—C11	0.9 (6)	C21—C22—C23—C24	0.0 (6)
C9—C10—C11—C12	−0.5 (6)	C22—C23—C24—C25	−0.2 (6)
C9—C10—C11—N2	−178.5 (4)	C22—C23—C24—N4	180.0 (4)
C10—C11—C12—C13	0.1 (6)	C23—C24—C25—C26	−0.3 (7)
N2—C11—C12—C13	178.1 (4)	N4—C24—C25—C26	179.5 (4)
C11—C12—C13—C8	−0.1 (6)	C24—C25—C26—C21	1.1 (7)
C9—C8—C13—C12	0.5 (6)	C22—C21—C26—C25	−1.3 (6)
N1—C8—C13—C12	174.2 (4)	N3—C21—C26—C25	172.4 (4)
S1—C1—N1—C8	5.4 (6)	S2—C14—N3—C21	9.1 (7)
C2—C1—N1—C8	−173.8 (3)	C15—C14—N3—C21	−167.8 (4)
C9—C8—N1—C1	−118.3 (4)	C22—C21—N3—C14	−115.0 (5)
C13—C8—N1—C1	68.0 (5)	C26—C21—N3—C14	71.4 (6)
C10—C11—N2—O1	−179.0 (4)	C23—C24—N4—O3	8.0 (6)
C10—C11—N2—O2	1.4 (6)	C23—C24—N4—O4	−172.0 (4)
C12—C11—N2—O1	2.9 (6)	C25—C24—N4—O3	−171.8 (4)
C12—C11—N2—O2	−176.7 (4)	C25—C24—N4—O4	8.2 (6)