[1,5-Bis(4-fluoro-phen-yl)thio-carbazo-nato-κN,S]phenyl-mercury(II) dichloro-methane hemisolvate.

In the title compound, [Hg(C(6)H(5))(C(13)H(9)F(2)N(4)S)]·0.5CH(2)Cl(2), the Hg(C(6)H(5)) units are twisted out of the planes of the thio-carbazo-nate ligands by 61.49 (10) and 67.79 (11)° in the two complex mol-ecules comprising the asymmetric unit. Important geometrical parameters include Hg-C = 2.079 (4) and 2.087 (4) Å, Hg-S = 2.3869 (10) and 2.3889 (11) Å, and C-Hg-S = 166.42 (12) and 168.09 (13)°. Weak intramolecular Hg-N bonding inter-actions of 2.589 (4) and 2.626 (4) Å are observed. In the crystal, C-H⋯Cl, C-H⋯F, C-H⋯N, C-H⋯π and π-π [centroid-centroid distances = 3.648 (3) and 3.641 (3) Å] inter-actions, create parallel planes along [101].

Related literature

For general background to thio­carbodiazo­natomercury(II) complexes, see: Irving et al. (1949 ▶); Webb et al. (1950 ▶); von Eschwege et al. (2011 ▶). For synthetic procedures relating to the title compound, see: Mirkhalaf et al. (1998 ▶); von Eschwege et al. (2008 ▶). For details of the superimposed fitting of structures with Mercury, see: Weng et al. (2008a ▶,b ▶).

Experimental

Crystal data

[Hg(C6H5)(C13H9F2N4S)]·0.5CH2Cl2

M = 611.46

Monoclinic,

a = 31.996 (3) Å

b = 10.1889 (9) Å

c = 26.892 (2) Å

β = 116.818 (1)°

V = 7823.8 (12) Å3

Z = 16

Mo Kα radiation

μ = 8.14 mm−1

T = 100 K

0.5 × 0.41 × 0.12 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.106, T max = 0.441

94461 measured reflections

9726 independent reflections

8965 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.074

S = 1.21

9726 reflections

514 parameters

H-atom parameters constrained

Δρmax = 3.10 e Å−3

Δρmin = −2.47 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050331/zq2140sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050331/zq2140Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Hg(C6H5)(C13H9F2N4S)]·0.5CH2Cl2	F(000) = 4656
Mr = 611.46	Dx = 2.076 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9279 reflections
a = 31.996 (3) Å	θ = 2.7–28.3°
b = 10.1889 (9) Å	µ = 8.14 mm−1
c = 26.892 (2) Å	T = 100 K
β = 116.818 (1)°	Plate, red
V = 7823.8 (12) Å3	0.5 × 0.41 × 0.12 mm
Z = 16

Bruker APEX DUO 4K CCD diffractometer	9726 independent reflections
graphite	8965 reflections with I > 2σ(I)
Detector resolution: 8.4 pixels mm-1	Rint = 0.045
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −42→42
Tmin = 0.106, Tmax = 0.441	k = −13→13
94461 measured reflections	l = −35→35

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.21	w = 1/[σ2(Fo2) + (0.0197P)2 + 88.7759P] where P = (Fo2 + 2Fc2)/3
9726 reflections	(Δ/σ)max = 0.003
514 parameters	Δρmax = 3.10 e Å−3
0 restraints	Δρmin = −2.47 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 10 s/frame. A total of 2980 frames were collected with a frame width of 0.5° covering up to θ = 28.33° with 99.5% completeness accomplished.Analytical data: M.p. 208 °C; λmax (dichloromethane) 471 nm; 1H (300 MHz, CDCl3) 7.06 – 7.99 (13 H, m, 2 × C6H4F & 1 × C6H5).

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.

	x	y	z	Uiso*/Ueq
C1	0.46620 (14)	0.7851 (4)	0.15534 (16)	0.0126 (8)
C2	0.35329 (14)	0.7322 (4)	0.04266 (17)	0.0150 (8)
C3	0.34667 (15)	0.5979 (4)	0.03934 (18)	0.0180 (9)
H3	0.3697	0.5413	0.0655	0.022*
C4	0.30560 (16)	0.5467 (5)	−0.00303 (19)	0.0215 (9)
H4	0.3003	0.4547	−0.006	0.026*
C5	0.27293 (16)	0.6309 (5)	−0.04042 (19)	0.0226 (10)
C6	0.27872 (15)	0.7644 (5)	−0.03753 (19)	0.0214 (9)
H6	0.2554	0.8203	−0.0637	0.026*
C7	0.31949 (15)	0.8161 (5)	0.00454 (18)	0.0175 (9)
H7	0.3244	0.9083	0.0074	0.021*
C8	0.57739 (14)	0.6773 (4)	0.25709 (17)	0.0148 (8)
C9	0.61666 (14)	0.7429 (4)	0.29689 (17)	0.0148 (8)
H9	0.6175	0.8361	0.2977	0.018*
C10	0.65435 (15)	0.6717 (5)	0.33513 (17)	0.0183 (9)
H10	0.6811	0.7149	0.3625	0.022*
C11	0.65210 (15)	0.5387 (4)	0.33253 (18)	0.0183 (9)
C12	0.61417 (17)	0.4698 (5)	0.2933 (2)	0.0226 (10)
H12	0.6141	0.3766	0.2924	0.027*
C13	0.57615 (16)	0.5418 (4)	0.25539 (19)	0.0195 (9)
H13	0.5494	0.4977	0.2283	0.023*
C14	0.60941 (14)	1.1066 (4)	0.25128 (18)	0.0156 (8)
C15	0.62304 (15)	1.1764 (4)	0.21641 (19)	0.0181 (9)
H15	0.6017	1.1858	0.1781	0.022*
C16	0.66723 (16)	1.2325 (5)	0.2365 (2)	0.0200 (9)
H16	0.6757	1.2804	0.2122	0.024*
C17	0.69890 (16)	1.2186 (5)	0.2922 (2)	0.0219 (9)
H17	0.7294	1.255	0.306	0.026*
C18	0.68571 (16)	1.1510 (5)	0.32781 (19)	0.0211 (9)
H18	0.7073	1.1417	0.3661	0.025*
C19	0.64101 (16)	1.0969 (4)	0.30767 (18)	0.0180 (9)
H19	0.632	1.053	0.3325	0.022*
N1	0.54016 (12)	0.7614 (4)	0.22209 (14)	0.0145 (7)
N2	0.50339 (12)	0.7028 (3)	0.18737 (14)	0.0133 (7)
N3	0.43071 (12)	0.7197 (4)	0.11738 (14)	0.0142 (7)
N4	0.39362 (12)	0.7908 (4)	0.08385 (14)	0.0157 (7)
H4A	0.3945	0.8767	0.0877	0.019*
S1	0.46396 (3)	0.95572 (10)	0.16432 (4)	0.01423 (19)
Hg1	0.544460 (5)	1.014330 (16)	0.216419 (7)	0.01517 (5)
C20	0.54721 (15)	0.8218 (5)	0.09362 (18)	0.0172 (8)
C21	0.65986 (14)	0.7796 (4)	0.20752 (17)	0.0151 (8)
C22	0.66609 (15)	0.6447 (4)	0.21190 (18)	0.0173 (8)
H22	0.643	0.5882	0.1858	0.021*
C23	0.70632 (16)	0.5930 (5)	0.25465 (18)	0.0193 (9)
H23	0.7113	0.5009	0.258	0.023*
C24	0.73905 (15)	0.6773 (5)	0.29230 (18)	0.0193 (9)
C25	0.73349 (15)	0.8114 (5)	0.28909 (19)	0.0190 (9)
H25	0.7564	0.8671	0.316	0.023*
C26	0.69359 (15)	0.8636 (5)	0.24555 (19)	0.0185 (9)
H26	0.6893	0.9559	0.2417	0.022*
C27	0.43996 (15)	0.6906 (5)	−0.00737 (18)	0.0177 (9)
C28	0.44574 (16)	0.5554 (5)	−0.0017 (2)	0.0228 (10)
H28	0.4746	0.5199	0.0251	0.027*
C29	0.40969 (19)	0.4717 (5)	−0.0349 (2)	0.0281 (11)
H29	0.4132	0.3791	−0.0312	0.034*
C30	0.36822 (17)	0.5281 (5)	−0.0739 (2)	0.0240 (10)
C31	0.36194 (16)	0.6599 (5)	−0.08133 (19)	0.0242 (10)
H31	0.3334	0.6946	−0.1093	0.029*
C32	0.39781 (15)	0.7428 (5)	−0.04747 (18)	0.0202 (9)
H32	0.3938	0.8352	−0.0515	0.024*
C33	0.39213 (15)	1.1012 (5)	0.01027 (19)	0.0187 (9)
C34	0.37593 (16)	1.1470 (4)	0.0471 (2)	0.0205 (9)
H34	0.397	1.1533	0.0856	0.025*
C35	0.32924 (17)	1.1840 (5)	0.0282 (2)	0.0240 (10)
H35	0.3186	1.2153	0.0539	0.029*
C36	0.29825 (16)	1.1749 (5)	−0.0282 (2)	0.0267 (11)
H36	0.2663	1.198	−0.0411	0.032*
C37	0.31419 (17)	1.1320 (5)	−0.0653 (2)	0.0257 (10)
H37	0.2932	1.1272	−0.1039	0.031*
C38	0.36084 (16)	1.0957 (5)	−0.04644 (19)	0.0211 (9)
H38	0.3715	1.0671	−0.0724	0.025*
N5	0.47415 (12)	0.7835 (4)	0.02619 (15)	0.0159 (7)
N6	0.51276 (13)	0.7329 (4)	0.06020 (15)	0.0183 (8)
N7	0.58460 (13)	0.7619 (4)	0.13032 (15)	0.0171 (7)
N8	0.61938 (13)	0.8373 (4)	0.16571 (15)	0.0178 (7)
H8	0.617	0.9233	0.1629	0.021*
F1	0.23290 (10)	0.5798 (3)	−0.08167 (13)	0.0331 (7)
F2	0.68937 (10)	0.4681 (3)	0.36991 (12)	0.0283 (7)
F3	0.33195 (11)	0.4477 (3)	−0.10507 (13)	0.0363 (8)
F4	0.77784 (10)	0.6248 (3)	0.33508 (12)	0.0272 (6)
S2	0.54317 (4)	0.99363 (11)	0.08664 (4)	0.0172 (2)
Hg2	0.460639 (5)	1.031777 (17)	0.040790 (7)	0.01692 (5)
C39	0.47037 (19)	0.3912 (5)	0.1214 (2)	0.0325 (12)
H39A	0.4732	0.4864	0.1295	0.039*
H39B	0.4408	0.3765	0.0871	0.039*
Cl1	0.51796 (5)	0.33931 (16)	0.10993 (6)	0.0417 (3)
Cl2	0.46844 (5)	0.30584 (15)	0.17705 (6)	0.0385 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0108 (17)	0.0143 (19)	0.0125 (18)	0.0015 (15)	0.0050 (15)	0.0012 (14)
C2	0.0100 (18)	0.021 (2)	0.0123 (18)	−0.0017 (15)	0.0031 (15)	−0.0010 (15)
C3	0.017 (2)	0.018 (2)	0.0162 (19)	0.0010 (16)	0.0046 (17)	0.0004 (16)
C4	0.021 (2)	0.018 (2)	0.024 (2)	−0.0047 (17)	0.0082 (19)	−0.0049 (17)
C5	0.014 (2)	0.030 (3)	0.017 (2)	−0.0043 (18)	0.0019 (17)	−0.0067 (18)
C6	0.0124 (19)	0.024 (2)	0.020 (2)	−0.0002 (17)	0.0006 (17)	−0.0003 (18)
C7	0.0141 (19)	0.018 (2)	0.017 (2)	−0.0009 (16)	0.0041 (17)	−0.0006 (16)
C8	0.0110 (18)	0.018 (2)	0.0136 (18)	0.0004 (15)	0.0040 (16)	−0.0014 (15)
C9	0.0150 (19)	0.0117 (19)	0.0150 (18)	−0.0004 (15)	0.0042 (16)	−0.0032 (15)
C10	0.0124 (19)	0.025 (2)	0.0130 (18)	0.0003 (17)	0.0021 (16)	−0.0022 (16)
C11	0.0152 (19)	0.019 (2)	0.0175 (19)	0.0085 (16)	0.0046 (17)	0.0034 (16)
C12	0.021 (2)	0.013 (2)	0.028 (2)	0.0040 (17)	0.0063 (19)	0.0022 (17)
C13	0.015 (2)	0.015 (2)	0.023 (2)	0.0010 (16)	0.0035 (17)	−0.0018 (17)
C14	0.0098 (17)	0.0118 (19)	0.023 (2)	−0.0026 (14)	0.0049 (16)	−0.0031 (16)
C15	0.016 (2)	0.013 (2)	0.021 (2)	−0.0006 (16)	0.0047 (17)	−0.0005 (16)
C16	0.018 (2)	0.016 (2)	0.025 (2)	−0.0034 (17)	0.0100 (18)	0.0008 (17)
C17	0.015 (2)	0.017 (2)	0.029 (2)	−0.0030 (16)	0.0056 (19)	−0.0023 (18)
C18	0.019 (2)	0.017 (2)	0.020 (2)	−0.0034 (17)	0.0013 (18)	−0.0019 (17)
C19	0.020 (2)	0.011 (2)	0.020 (2)	−0.0009 (16)	0.0073 (18)	−0.0008 (16)
N1	0.0108 (16)	0.0164 (18)	0.0133 (15)	−0.0001 (13)	0.0027 (13)	0.0005 (13)
N2	0.0096 (15)	0.0137 (17)	0.0142 (16)	0.0000 (13)	0.0032 (13)	0.0009 (13)
N3	0.0118 (16)	0.0141 (17)	0.0140 (16)	0.0005 (13)	0.0035 (14)	0.0007 (13)
N4	0.0112 (16)	0.0156 (18)	0.0145 (16)	−0.0008 (13)	0.0006 (14)	0.0002 (13)
S1	0.0113 (4)	0.0120 (5)	0.0158 (4)	0.0002 (3)	0.0030 (4)	0.0009 (4)
Hg1	0.01147 (7)	0.01376 (8)	0.01828 (8)	−0.00258 (5)	0.00496 (6)	−0.00227 (6)
C20	0.0146 (19)	0.019 (2)	0.0162 (19)	0.0007 (16)	0.0054 (17)	0.0003 (16)
C21	0.0112 (18)	0.019 (2)	0.0137 (18)	0.0025 (15)	0.0041 (16)	0.0023 (15)
C22	0.0142 (19)	0.020 (2)	0.0155 (19)	0.0001 (16)	0.0052 (16)	−0.0032 (16)
C23	0.020 (2)	0.016 (2)	0.020 (2)	0.0028 (17)	0.0070 (18)	0.0005 (16)
C24	0.0128 (19)	0.024 (2)	0.0163 (19)	0.0040 (17)	0.0025 (17)	0.0042 (17)
C25	0.0123 (19)	0.021 (2)	0.020 (2)	−0.0021 (16)	0.0038 (17)	0.0001 (17)
C26	0.0148 (19)	0.016 (2)	0.022 (2)	0.0014 (16)	0.0065 (17)	0.0006 (17)
C27	0.0136 (19)	0.022 (2)	0.0164 (19)	0.0006 (16)	0.0056 (17)	−0.0018 (16)
C28	0.017 (2)	0.022 (2)	0.026 (2)	0.0026 (18)	0.0071 (19)	−0.0016 (18)
C29	0.029 (3)	0.020 (2)	0.037 (3)	−0.002 (2)	0.016 (2)	−0.009 (2)
C30	0.023 (2)	0.030 (3)	0.021 (2)	−0.009 (2)	0.0118 (19)	−0.0111 (19)
C31	0.016 (2)	0.037 (3)	0.015 (2)	−0.0026 (19)	0.0024 (17)	0.0001 (19)
C32	0.015 (2)	0.023 (2)	0.019 (2)	0.0002 (17)	0.0049 (17)	0.0016 (17)
C33	0.0117 (18)	0.019 (2)	0.023 (2)	0.0028 (16)	0.0065 (17)	0.0044 (17)
C34	0.018 (2)	0.016 (2)	0.022 (2)	0.0022 (16)	0.0047 (18)	0.0013 (17)
C35	0.021 (2)	0.020 (2)	0.029 (2)	0.0062 (18)	0.010 (2)	0.0000 (19)
C36	0.014 (2)	0.026 (3)	0.034 (3)	0.0089 (18)	0.006 (2)	0.004 (2)
C37	0.019 (2)	0.026 (3)	0.022 (2)	0.0067 (19)	0.0014 (19)	0.0052 (19)
C38	0.020 (2)	0.023 (2)	0.018 (2)	0.0038 (18)	0.0073 (18)	0.0030 (17)
N5	0.0128 (16)	0.0198 (19)	0.0147 (16)	0.0020 (14)	0.0060 (14)	0.0011 (14)
N6	0.0127 (16)	0.022 (2)	0.0168 (17)	0.0016 (14)	0.0037 (14)	−0.0004 (14)
N7	0.0133 (16)	0.0204 (19)	0.0154 (17)	0.0021 (14)	0.0046 (14)	−0.0011 (14)
N8	0.0141 (17)	0.0177 (18)	0.0163 (17)	0.0013 (14)	0.0022 (14)	0.0011 (14)
F1	0.0203 (14)	0.0312 (17)	0.0299 (15)	−0.0072 (12)	−0.0044 (12)	−0.0097 (13)
F2	0.0210 (14)	0.0263 (15)	0.0261 (14)	0.0126 (12)	0.0005 (12)	0.0025 (12)
F3	0.0330 (17)	0.0390 (19)	0.0339 (17)	−0.0150 (14)	0.0124 (14)	−0.0188 (14)
F4	0.0171 (13)	0.0257 (15)	0.0253 (14)	0.0048 (11)	−0.0023 (11)	0.0051 (12)
S2	0.0127 (5)	0.0169 (5)	0.0192 (5)	0.0007 (4)	0.0048 (4)	0.0027 (4)
Hg2	0.01199 (8)	0.01754 (9)	0.01911 (8)	0.00276 (6)	0.00514 (6)	0.00486 (6)
C39	0.026 (3)	0.025 (3)	0.034 (3)	0.009 (2)	0.004 (2)	−0.006 (2)
Cl1	0.0363 (7)	0.0410 (8)	0.0430 (8)	0.0185 (6)	0.0138 (6)	0.0053 (6)
Cl2	0.0435 (8)	0.0335 (7)	0.0314 (6)	0.0023 (6)	0.0107 (6)	−0.0066 (5)

C1—N3	1.315 (5)	C20—S2	1.759 (5)
C1—N2	1.391 (5)	C21—C22	1.386 (6)
C1—S1	1.761 (4)	C21—C26	1.395 (6)
C2—C3	1.382 (6)	C21—N8	1.405 (5)
C2—C7	1.397 (6)	C22—C23	1.386 (6)
C2—N4	1.400 (5)	C22—H22	0.95
C3—C4	1.395 (6)	C23—C24	1.379 (6)
C3—H3	0.95	C23—H23	0.95
C4—C5	1.375 (7)	C24—F4	1.364 (5)
C4—H4	0.95	C24—C25	1.376 (7)
C5—F1	1.364 (5)	C25—C26	1.391 (6)
C5—C6	1.370 (7)	C25—H25	0.95
C6—C7	1.388 (6)	C26—H26	0.95
C6—H6	0.95	C27—C28	1.389 (7)
C7—H7	0.95	C27—C32	1.397 (6)
C8—C13	1.382 (6)	C27—N5	1.420 (6)
C8—C9	1.399 (5)	C28—C29	1.387 (7)
C8—N1	1.423 (5)	C28—H28	0.95
C9—C10	1.385 (6)	C29—C30	1.391 (7)
C9—H9	0.95	C29—H29	0.95
C10—C11	1.357 (7)	C30—F3	1.357 (5)
C10—H10	0.95	C30—C31	1.360 (8)
C11—F2	1.367 (5)	C31—C32	1.384 (6)
C11—C12	1.387 (6)	C31—H31	0.95
C12—C13	1.392 (6)	C32—H32	0.95
C12—H12	0.95	C33—C34	1.389 (7)
C13—H13	0.95	C33—C38	1.398 (6)
C14—C15	1.394 (6)	C33—Hg2	2.087 (4)
C14—C19	1.396 (6)	C34—C35	1.396 (6)
C14—Hg1	2.079 (4)	C34—H34	0.95
C15—C16	1.388 (6)	C35—C36	1.391 (7)
C15—H15	0.95	C35—H35	0.95
C16—C17	1.386 (6)	C36—C37	1.380 (8)
C16—H16	0.95	C36—H36	0.95
C17—C18	1.390 (7)	C37—C38	1.393 (6)
C17—H17	0.95	C37—H37	0.95
C18—C19	1.394 (6)	C38—H38	0.95
C18—H18	0.95	N5—N6	1.268 (5)
C19—H19	0.95	N5—Hg2	2.626 (4)
N1—N2	1.273 (5)	N7—N8	1.334 (5)
N1—Hg1	2.589 (4)	N8—H8	0.88
N3—N4	1.334 (5)	S2—Hg2	2.3889 (11)
N4—H4A	0.88	C39—Cl2	1.757 (6)
S1—Hg1	2.3869 (10)	C39—Cl1	1.765 (6)
C20—N7	1.309 (5)	C39—H39A	0.99
C20—N6	1.396 (6)	C39—H39B	0.99
N3—C1—N2	111.9 (4)	C22—C21—C26	120.8 (4)
N3—C1—S1	122.1 (3)	C22—C21—N8	121.9 (4)
N2—C1—S1	125.9 (3)	C26—C21—N8	117.3 (4)
C3—C2—C7	120.9 (4)	C23—C22—C21	119.4 (4)
C3—C2—N4	122.2 (4)	C23—C22—H22	120.3
C7—C2—N4	116.8 (4)	C21—C22—H22	120.3
C2—C3—C4	118.9 (4)	C24—C23—C22	119.1 (4)
C2—C3—H3	120.5	C24—C23—H23	120.5
C4—C3—H3	120.5	C22—C23—H23	120.5
C5—C4—C3	119.3 (4)	F4—C24—C25	119.0 (4)
C5—C4—H4	120.4	F4—C24—C23	118.4 (4)
C3—C4—H4	120.4	C25—C24—C23	122.6 (4)
F1—C5—C6	118.6 (4)	C24—C25—C26	118.4 (4)
F1—C5—C4	118.8 (4)	C24—C25—H25	120.8
C6—C5—C4	122.6 (4)	C26—C25—H25	120.8
C5—C6—C7	118.4 (4)	C25—C26—C21	119.7 (4)
C5—C6—H6	120.8	C25—C26—H26	120.1
C7—C6—H6	120.8	C21—C26—H26	120.1
C6—C7—C2	119.8 (4)	C28—C27—C32	119.8 (4)
C6—C7—H7	120.1	C28—C27—N5	124.4 (4)
C2—C7—H7	120.1	C32—C27—N5	115.8 (4)
C13—C8—C9	120.3 (4)	C29—C28—C27	120.5 (4)
C13—C8—N1	125.2 (4)	C29—C28—H28	119.7
C9—C8—N1	114.4 (4)	C27—C28—H28	119.7
C10—C9—C8	119.9 (4)	C28—C29—C30	117.7 (5)
C10—C9—H9	120.1	C28—C29—H29	121.2
C8—C9—H9	120.1	C30—C29—H29	121.2
C11—C10—C9	118.5 (4)	F3—C30—C31	118.5 (5)
C11—C10—H10	120.8	F3—C30—C29	118.4 (5)
C9—C10—H10	120.8	C31—C30—C29	123.1 (4)
C10—C11—F2	118.6 (4)	C30—C31—C32	118.8 (4)
C10—C11—C12	123.5 (4)	C30—C31—H31	120.6
F2—C11—C12	117.8 (4)	C32—C31—H31	120.6
C11—C12—C13	117.8 (4)	C31—C32—C27	120.0 (5)
C11—C12—H12	121.1	C31—C32—H32	120
C13—C12—H12	121.1	C27—C32—H32	120
C8—C13—C12	120.0 (4)	C34—C33—C38	118.5 (4)
C8—C13—H13	120	C34—C33—Hg2	119.8 (3)
C12—C13—H13	120	C38—C33—Hg2	121.6 (4)
C15—C14—C19	118.3 (4)	C33—C34—C35	121.0 (4)
C15—C14—Hg1	118.7 (3)	C33—C34—H34	119.5
C19—C14—Hg1	123.0 (3)	C35—C34—H34	119.5
C16—C15—C14	121.3 (4)	C36—C35—C34	119.8 (5)
C16—C15—H15	119.3	C36—C35—H35	120.1
C14—C15—H15	119.3	C34—C35—H35	120.1
C17—C16—C15	119.9 (4)	C37—C36—C35	119.7 (4)
C17—C16—H16	120	C37—C36—H36	120.2
C15—C16—H16	120	C35—C36—H36	120.2
C16—C17—C18	119.6 (4)	C36—C37—C38	120.4 (4)
C16—C17—H17	120.2	C36—C37—H37	119.8
C18—C17—H17	120.2	C38—C37—H37	119.8
C17—C18—C19	120.4 (4)	C37—C38—C33	120.6 (5)
C17—C18—H18	119.8	C37—C38—H38	119.7
C19—C18—H18	119.8	C33—C38—H38	119.7
C18—C19—C14	120.5 (4)	N6—N5—C27	114.1 (4)
C18—C19—H19	119.8	N6—N5—Hg2	117.1 (3)
C14—C19—H19	119.8	C27—N5—Hg2	127.3 (3)
N2—N1—C8	115.1 (4)	N5—N6—C20	115.5 (4)
N2—N1—Hg1	118.6 (3)	C20—N7—N8	117.0 (4)
C8—N1—Hg1	125.9 (3)	N7—N8—C21	120.1 (4)
N1—N2—C1	114.9 (4)	N7—N8—H8	119.9
C1—N3—N4	116.3 (4)	C21—N8—H8	119.9
N3—N4—C2	121.6 (4)	C20—S2—Hg2	103.17 (15)
N3—N4—H4A	119.2	C33—Hg2—S2	168.09 (13)
C2—N4—H4A	119.2	C33—Hg2—N5	118.83 (15)
C1—S1—Hg1	103.15 (14)	S2—Hg2—N5	72.67 (8)
C14—Hg1—S1	166.42 (12)	Cl2—C39—Cl1	111.4 (3)
C14—Hg1—N1	119.51 (14)	Cl2—C39—H39A	109.3
S1—Hg1—N1	73.36 (8)	Cl1—C39—H39A	109.3
N7—C20—N6	111.7 (4)	Cl2—C39—H39B	109.3
N7—C20—S2	122.9 (3)	Cl1—C39—H39B	109.3
N6—C20—S2	125.3 (3)	H39A—C39—H39B	108
C7—C2—C3—C4	0.3 (7)	C26—C21—C22—C23	0.1 (7)
N4—C2—C3—C4	−179.8 (4)	N8—C21—C22—C23	−178.7 (4)
C2—C3—C4—C5	0.2 (7)	C21—C22—C23—C24	0.7 (7)
C3—C4—C5—F1	180.0 (4)	C22—C23—C24—F4	178.2 (4)
C3—C4—C5—C6	−0.8 (8)	C22—C23—C24—C25	−0.2 (7)
F1—C5—C6—C7	180.0 (4)	F4—C24—C25—C26	−179.4 (4)
C4—C5—C6—C7	0.7 (8)	C23—C24—C25—C26	−1.1 (7)
C5—C6—C7—C2	−0.2 (7)	C24—C25—C26—C21	1.9 (7)
C3—C2—C7—C6	−0.3 (7)	C22—C21—C26—C25	−1.4 (7)
N4—C2—C7—C6	179.7 (4)	N8—C21—C26—C25	177.5 (4)
C13—C8—C9—C10	−0.6 (7)	C32—C27—C28—C29	−1.2 (8)
N1—C8—C9—C10	177.0 (4)	N5—C27—C28—C29	177.4 (5)
C8—C9—C10—C11	0.4 (7)	C27—C28—C29—C30	0.6 (8)
C9—C10—C11—F2	179.5 (4)	C28—C29—C30—F3	−177.2 (5)
C9—C10—C11—C12	0.5 (8)	C28—C29—C30—C31	1.1 (8)
C10—C11—C12—C13	−1.2 (8)	F3—C30—C31—C32	176.2 (4)
F2—C11—C12—C13	179.8 (4)	C29—C30—C31—C32	−2.1 (8)
C9—C8—C13—C12	−0.2 (7)	C30—C31—C32—C27	1.4 (7)
N1—C8—C13—C12	−177.5 (4)	C28—C27—C32—C31	0.1 (7)
C11—C12—C13—C8	1.0 (7)	N5—C27—C32—C31	−178.5 (4)
C19—C14—C15—C16	1.5 (7)	C38—C33—C34—C35	1.5 (7)
Hg1—C14—C15—C16	−175.5 (3)	Hg2—C33—C34—C35	−174.8 (4)
C14—C15—C16—C17	0.6 (7)	C33—C34—C35—C36	0.1 (8)
C15—C16—C17—C18	−1.5 (7)	C34—C35—C36—C37	−1.4 (8)
C16—C17—C18—C19	0.3 (7)	C35—C36—C37—C38	1.1 (8)
C17—C18—C19—C14	1.8 (7)	C36—C37—C38—C33	0.5 (8)
C15—C14—C19—C18	−2.7 (7)	C34—C33—C38—C37	−1.8 (7)
Hg1—C14—C19—C18	174.2 (3)	Hg2—C33—C38—C37	174.4 (4)
C13—C8—N1—N2	0.5 (6)	C28—C27—N5—N6	4.7 (7)
C9—C8—N1—N2	−176.9 (4)	C32—C27—N5—N6	−176.7 (4)
C13—C8—N1—Hg1	−172.6 (4)	C28—C27—N5—Hg2	−160.7 (4)
C9—C8—N1—Hg1	9.9 (5)	C32—C27—N5—Hg2	17.9 (6)
C8—N1—N2—C1	176.6 (4)	C27—N5—N6—C20	179.7 (4)
Hg1—N1—N2—C1	−9.7 (5)	Hg2—N5—N6—C20	−13.3 (5)
N3—C1—N2—N1	174.9 (4)	N7—C20—N6—N5	175.2 (4)
S1—C1—N2—N1	−7.4 (6)	S2—C20—N6—N5	−7.4 (6)
N2—C1—N3—N4	−178.8 (4)	N6—C20—N7—N8	−178.1 (4)
S1—C1—N3—N4	3.5 (5)	S2—C20—N7—N8	4.4 (6)
C1—N3—N4—C2	−178.5 (4)	C20—N7—N8—C21	177.7 (4)
C3—C2—N4—N3	9.5 (7)	C22—C21—N8—N7	3.1 (7)
C7—C2—N4—N3	−170.6 (4)	C26—C21—N8—N7	−175.8 (4)
N3—C1—S1—Hg1	−162.5 (3)	N7—C20—S2—Hg2	−158.9 (4)
N2—C1—S1—Hg1	20.0 (4)	N6—C20—S2—Hg2	23.9 (4)
C15—C14—Hg1—S1	−42.8 (8)	C34—C33—Hg2—S2	−48.5 (9)
C19—C14—Hg1—S1	140.3 (4)	C38—C33—Hg2—S2	135.3 (5)
C15—C14—Hg1—N1	117.4 (3)	C34—C33—Hg2—N5	115.8 (4)
C19—C14—Hg1—N1	−59.4 (4)	C38—C33—Hg2—N5	−60.4 (4)
C1—S1—Hg1—C14	147.5 (6)	C20—S2—Hg2—C33	147.6 (6)
C1—S1—Hg1—N1	−14.59 (16)	C20—S2—Hg2—N5	−17.98 (17)
N2—N1—Hg1—C14	−158.7 (3)	N6—N5—Hg2—C33	−155.6 (3)
C8—N1—Hg1—C14	14.3 (4)	C27—N5—Hg2—C33	9.5 (4)
N2—N1—Hg1—S1	16.6 (3)	N6—N5—Hg2—S2	21.1 (3)
C8—N1—Hg1—S1	−170.5 (3)	C27—N5—Hg2—S2	−173.9 (4)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···Cl1	0.95	2.77	3.598 (5)	146.
C31—H31···F4i	0.95	2.53	3.413 (6)	155.
C39—H39A···N2	0.99	2.62	3.558 (6)	158.
C7—H7···Cg1ii	0.95	2.54	3.451 (5)	162
C12—H12···Cg2iii	0.95	2.70	3.516 (6)	144
C26—H26···Cg2ii	0.95	2.69	3.500 (5)	144

Cg(X)···Cg(Y)	Cg···Cg	Alpha	Beta	Gamma	Cg(X)perp	Cg(X)perp
Cg1···Cg4i	3.648 (3)	6.3 (2)	21.65	27.98	3.221 (2)	3.391 (2)
Cg2···Cg3i	3.641 (3)	4.1 (2)	27.95	24.04	3.325 (2)	3.216 (2)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯Cl1	0.95	2.77	3.598 (5)	146
C31—H31⋯F4i	0.95	2.53	3.413 (6)	155
C39—H39A⋯N2	0.99	2.62	3.558 (6)	158
C7—H7⋯Cg1ii	0.95	2.54	3.451 (5)	162
C12—H12⋯Cg2iii	0.95	2.70	3.516 (6)	144
C26—H26⋯Cg2ii	0.95	2.69	3.500 (5)	144

Symmetry codes: (i) ; (ii) ; (iii) .