Bis(tetra-phenyl-phospho-nium) bis-[N-(trifluoro-methyl-sulfon-yl)dithio-carbimato(2-)-κS,S']zincate(II).

The title salt, (C(24)H(20)P)(2)[Zn(C(2)F(3)NO(2)S(3))(2)], consists of a complex dianion and two tetra-phenyl-phospho-nium cations. The Zn(II) ion displays a distorted tetra-hedral coordination environment with four S atoms from two S,S'-chelated N-(trifluoro-methyl-sulfonyl-)dithio-carbimate anions. In the crystal, besides the ionic inter-action of the oppositely charged ions, inter-molecular C-H⋯O inter-actions between cations and anions are observed. One of the cations inter-acts with an inversion-related equivalent by π-π stacking between phenyl rings, with a centroid-centroid distance of 3.932 (4) Å.

Related literature

For the anti­fungal and vulcanization activities and crystal structures of dithio­carbimato complexes, see: Amim et al. (2011 ▶); Alves et al. (2009 ▶); Mariano et al. (2007 ▶); Oliveira et al. (2007 ▶); Perpétuo et al. (2003 ▶). For further synthetic details, see: Franca et al. (2006 ▶). For other literature related to fungicides, see: Hogarth (2005 ▶).

Experimental

Crystal data

(C24H20P)2[Zn(C2F3NO2S3)2]

M = 1190.53

Monoclinic,

a = 8.8461 (1) Å

b = 29.1869 (5) Å

c = 20.6963 (3) Å

β = 93.578 (1)°

V = 5333.17 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.82 mm−1

T = 295 K

0.42 × 0.18 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.758, T max = 0.950

57739 measured reflections

11977 independent reflections

8307 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.169

S = 1.05

11977 reflections

646 parameters

H-atom parameters constrained

Δρmax = 1.18 e Å−3

Δρmin = −1.66 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681105207X/pk2371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105207X/pk2371Isup2.hkl

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

(C24H20P)2[Zn(C2F3NO2S3)2]	F(000) = 2432
Mr = 1190.53	Dx = 1.483 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.8461 (1) Å	Cell parameters from 80040 reflections
b = 29.1869 (5) Å	θ = 2.9–27.5°
c = 20.6963 (3) Å	µ = 0.82 mm−1
β = 93.578 (1)°	T = 295 K
V = 5333.17 (13) Å3	Prism, colourless
Z = 4	0.42 × 0.18 × 0.12 mm

Nonius KappaCCD diffractometer	11977 independent reflections
Radiation source: Enraf Nonius FR590	8307 reflections with I > 2σ(I)
graphite	Rint = 0.082
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.9°
CCD rotation images, thick slices scans	h = −11→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −37→37
Tmin = 0.758, Tmax = 0.950	l = −26→26
57739 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0872P)2 + 2.420P] where P = (Fo2 + 2Fc2)/3
11977 reflections	(Δ/σ)max = 0.003
646 parameters	Δρmax = 1.18 e Å−3
0 restraints	Δρmin = −1.66 e Å−3

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
Zn	0.76875 (4)	0.258126 (13)	1.300410 (19)	0.05905 (14)
S1	0.76765 (13)	0.32502 (3)	1.36222 (5)	0.0744 (3)
S2	0.89252 (11)	0.30995 (3)	1.23596 (4)	0.0636 (2)
S3	0.88481 (12)	0.42771 (3)	1.34592 (5)	0.0706 (2)
S4	0.57897 (9)	0.20559 (3)	1.26862 (5)	0.0615 (2)
S5	0.87243 (10)	0.18826 (3)	1.33924 (5)	0.0658 (2)
S6	0.77346 (10)	0.08409 (3)	1.33543 (4)	0.0600 (2)
P1	0.58019 (9)	0.36494 (3)	1.07700 (4)	0.0529 (2)
P2	0.41864 (8)	0.12861 (3)	1.04277 (4)	0.04373 (18)
F1	0.8570 (4)	0.48605 (10)	1.25094 (14)	0.1171 (10)
F2	1.0842 (3)	0.47099 (9)	1.28085 (14)	0.1085 (9)
F3	0.9532 (4)	0.51320 (8)	1.33994 (13)	0.1030 (9)
F4	0.6206 (4)	0.03089 (10)	1.25260 (17)	0.1194 (10)
F5	0.7129 (4)	−0.00242 (9)	1.33781 (18)	0.1227 (11)
F6	0.5171 (3)	0.03994 (10)	1.34194 (19)	0.1285 (11)
N1	0.9004 (3)	0.39051 (10)	1.29069 (13)	0.0605 (7)
N2	0.6657 (3)	0.12278 (9)	1.30365 (13)	0.0559 (6)
O1	0.7346 (3)	0.43889 (9)	1.36095 (12)	0.0706 (2)
O2	0.9950 (3)	0.42280 (8)	1.39932 (12)	0.0706 (2)
O3	0.7885 (4)	0.08521 (10)	1.40437 (13)	0.0839 (8)
O4	0.9063 (3)	0.07468 (9)	1.30165 (13)	0.0758 (7)
C1	0.8577 (3)	0.34775 (11)	1.29750 (15)	0.0537 (7)
C2	0.9492 (5)	0.47687 (14)	1.3012 (2)	0.0765 (11)
C3	0.7047 (3)	0.16624 (11)	1.30466 (14)	0.0503 (7)
C4	0.6486 (5)	0.03583 (14)	1.3155 (3)	0.0853 (12)
C5	0.4940 (4)	0.36160 (13)	1.15287 (17)	0.0638 (9)
C6	0.3858 (6)	0.32851 (19)	1.1625 (2)	0.0986 (15)
H6	0.3616	0.3069	1.1305	0.118*
C7	0.3137 (7)	0.3277 (3)	1.2198 (3)	0.128 (2)
H7	0.2419	0.3052	1.2268	0.153*
C8	0.3489 (7)	0.3605 (3)	1.2668 (3)	0.125 (2)
H8	0.2972	0.3608	1.3046	0.151*
C9	0.4583 (6)	0.3920 (2)	1.2581 (2)	0.1071 (17)
H9	0.4846	0.413	1.2908	0.129*
C10	0.5303 (4)	0.39325 (15)	1.20132 (18)	0.0744 (10)
H10	0.6037	0.4154	1.1953	0.089*
C11	0.6968 (4)	0.31543 (11)	1.06493 (16)	0.0558 (8)
C12	0.6925 (4)	0.27720 (12)	1.10471 (17)	0.0664 (9)
H12	0.6242	0.2759	1.1371	0.08*
C13	0.7902 (6)	0.24120 (13)	1.0960 (2)	0.0816 (13)
H13	0.7874	0.2157	1.1228	0.098*
C14	0.8906 (6)	0.24230 (15)	1.0487 (3)	0.0889 (14)
H14	0.9562	0.2178	1.0436	0.107*
C15	0.8946 (5)	0.27990 (17)	1.0084 (2)	0.0878 (12)
H15	0.9617	0.2805	0.9755	0.105*
C16	0.7991 (4)	0.31657 (14)	1.01673 (18)	0.0693 (9)
H16	0.8034	0.3421	0.99	0.083*
C17	0.7020 (4)	0.41366 (11)	1.07582 (15)	0.0537 (7)
C18	0.8430 (4)	0.41156 (14)	1.11035 (18)	0.0672 (9)
H18	0.8731	0.3851	1.1326	0.081*
C19	0.9370 (5)	0.44945 (15)	1.1109 (2)	0.0793 (11)
H19	1.0305	0.4485	1.1341	0.095*
C20	0.8941 (6)	0.48820 (16)	1.0781 (2)	0.0939 (14)
H20	0.9586	0.5134	1.0787	0.113*
C21	0.7568 (6)	0.49019 (16)	1.0441 (3)	0.1064 (17)
H21	0.7281	0.5167	1.0216	0.128*
C22	0.6601 (5)	0.45280 (13)	1.0432 (2)	0.0794 (11)
H22	0.5664	0.4543	1.0203	0.095*
C23	0.4320 (3)	0.37039 (11)	1.01393 (16)	0.0536 (7)
C24	0.2849 (4)	0.38278 (15)	1.0277 (2)	0.0750 (10)
H24	0.2615	0.3879	1.0703	0.09*
C25	0.1748 (4)	0.38742 (15)	0.9783 (2)	0.0790 (11)
H25	0.0768	0.3953	0.9879	0.095*
C26	0.2071 (4)	0.38068 (13)	0.9152 (2)	0.0698 (10)
H26	0.1316	0.3839	0.8822	0.084*
C27	0.3520 (4)	0.36912 (14)	0.90089 (19)	0.0698 (9)
H27	0.3748	0.3649	0.858	0.084*
C28	0.4642 (4)	0.36372 (12)	0.95011 (16)	0.0616 (8)
H28	0.5617	0.3556	0.9401	0.074*
C29	0.6183 (3)	0.12592 (9)	1.06577 (13)	0.0418 (6)
C30	0.6682 (3)	0.12508 (10)	1.13043 (14)	0.0475 (6)
H30	0.5996	0.129	1.1623	0.057*
C31	0.8211 (3)	0.11840 (11)	1.14776 (15)	0.0525 (7)
H31	0.8553	0.1173	1.1911	0.063*
C32	0.9212 (3)	0.11350 (11)	1.09979 (16)	0.0527 (7)
H32	1.0234	0.1087	1.1112	0.063*
C33	0.8732 (3)	0.11551 (11)	1.03584 (16)	0.0528 (7)
H33	0.9427	0.1127	1.0042	0.063*
C34	0.7213 (3)	0.12172 (11)	1.01815 (15)	0.0507 (7)
H34	0.6883	0.1231	0.9746	0.061*
C35	0.3211 (3)	0.13903 (11)	1.11472 (15)	0.0510 (7)
C36	0.2516 (4)	0.18093 (13)	1.12335 (18)	0.0625 (8)
H36	0.2526	0.2033	1.0914	0.075*
C37	0.1799 (4)	0.18924 (16)	1.1806 (2)	0.0781 (12)
H37	0.1345	0.2175	1.1871	0.094*
C38	0.1766 (4)	0.15591 (19)	1.22685 (19)	0.0811 (13)
H38	0.126	0.1614	1.2642	0.097*
C39	0.2459 (4)	0.11501 (17)	1.21909 (17)	0.0741 (11)
H39	0.2439	0.0929	1.2514	0.089*
C40	0.3192 (3)	0.10597 (13)	1.16364 (15)	0.0588 (8)
H40	0.3673	0.078	1.1588	0.071*
C41	0.3778 (3)	0.17355 (10)	0.98562 (14)	0.0489 (7)
C42	0.4799 (4)	0.20877 (11)	0.97580 (18)	0.0634 (9)
H42	0.5729	0.2095	0.9994	0.076*
C43	0.4427 (5)	0.24267 (13)	0.9309 (2)	0.0813 (12)
H43	0.5116	0.2659	0.9238	0.098*
C44	0.3046 (5)	0.24214 (14)	0.8969 (2)	0.0821 (12)
H44	0.2797	0.2652	0.8672	0.099*
C45	0.2028 (5)	0.20768 (15)	0.90656 (19)	0.0764 (11)
H45	0.1087	0.2079	0.8838	0.092*
C46	0.2388 (4)	0.17285 (13)	0.94965 (17)	0.0637 (9)
H46	0.171	0.149	0.9548	0.076*
C47	0.3599 (3)	0.07588 (10)	1.00384 (14)	0.0472 (6)
C48	0.2587 (4)	0.04559 (11)	1.02871 (16)	0.0559 (7)
H48	0.2166	0.0519	1.0678	0.067*
C49	0.2205 (4)	0.00612 (12)	0.99541 (19)	0.0668 (9)
H49	0.1515	−0.0141	1.012	0.08*
C50	0.2826 (4)	−0.00369 (12)	0.93823 (19)	0.0652 (9)
H50	0.257	−0.0307	0.9164	0.078*
C51	0.3832 (4)	0.02640 (14)	0.91288 (19)	0.0718 (10)
H51	0.4256	0.0197	0.874	0.086*
C52	0.4205 (4)	0.06620 (13)	0.94506 (17)	0.0670 (9)
H52	0.4868	0.0868	0.9275	0.08*

	U11	U22	U33	U12	U13	U23
Zn	0.0568 (2)	0.0545 (2)	0.0660 (3)	−0.00555 (17)	0.00531 (18)	−0.00531 (17)
S1	0.0976 (7)	0.0628 (5)	0.0662 (6)	−0.0187 (5)	0.0324 (5)	−0.0122 (4)
S2	0.0715 (6)	0.0615 (5)	0.0595 (5)	−0.0087 (4)	0.0170 (4)	−0.0105 (4)
S3	0.0793 (5)	0.0670 (5)	0.0670 (5)	−0.0189 (4)	0.0169 (4)	−0.0131 (4)
S4	0.0452 (4)	0.0540 (5)	0.0840 (6)	0.0023 (3)	−0.0067 (4)	−0.0026 (4)
S5	0.0505 (5)	0.0657 (5)	0.0792 (6)	−0.0007 (4)	−0.0113 (4)	0.0004 (4)
S6	0.0575 (5)	0.0567 (5)	0.0661 (5)	0.0069 (4)	0.0063 (4)	0.0033 (4)
P1	0.0490 (4)	0.0558 (5)	0.0538 (5)	−0.0078 (4)	0.0028 (3)	−0.0004 (4)
P2	0.0310 (3)	0.0516 (4)	0.0485 (4)	−0.0019 (3)	0.0015 (3)	−0.0016 (3)
F1	0.167 (3)	0.0894 (18)	0.0918 (18)	0.0078 (18)	−0.0169 (19)	0.0137 (14)
F2	0.114 (2)	0.0865 (17)	0.131 (2)	−0.0304 (16)	0.0558 (18)	−0.0042 (16)
F3	0.149 (3)	0.0613 (13)	0.0995 (18)	−0.0193 (15)	0.0172 (17)	−0.0187 (12)
F4	0.129 (2)	0.0855 (18)	0.139 (3)	−0.0078 (17)	−0.028 (2)	−0.0277 (17)
F5	0.119 (2)	0.0566 (14)	0.191 (3)	0.0091 (14)	0.003 (2)	0.0182 (17)
F6	0.0822 (18)	0.0841 (18)	0.223 (4)	−0.0127 (15)	0.042 (2)	0.006 (2)
N1	0.0680 (17)	0.0590 (16)	0.0557 (15)	−0.0102 (13)	0.0132 (13)	−0.0067 (12)
N2	0.0491 (14)	0.0513 (15)	0.0670 (17)	0.0027 (11)	0.0029 (12)	−0.0022 (12)
O1	0.0793 (5)	0.0670 (5)	0.0670 (5)	−0.0189 (4)	0.0169 (4)	−0.0131 (4)
O2	0.0793 (5)	0.0670 (5)	0.0670 (5)	−0.0189 (4)	0.0169 (4)	−0.0131 (4)
O3	0.102 (2)	0.0844 (18)	0.0650 (16)	0.0128 (16)	0.0061 (14)	0.0117 (13)
O4	0.0603 (14)	0.0793 (17)	0.0889 (18)	0.0176 (13)	0.0128 (13)	0.0008 (14)
C1	0.0469 (16)	0.0598 (19)	0.0545 (18)	−0.0038 (14)	0.0030 (14)	−0.0058 (14)
C2	0.097 (3)	0.062 (2)	0.072 (2)	−0.013 (2)	0.008 (2)	−0.0079 (19)
C3	0.0435 (15)	0.0583 (18)	0.0501 (16)	0.0029 (13)	0.0112 (13)	−0.0027 (13)
C4	0.076 (3)	0.060 (2)	0.121 (4)	0.006 (2)	0.009 (3)	0.003 (2)
C5	0.0565 (19)	0.073 (2)	0.062 (2)	−0.0092 (17)	0.0054 (16)	0.0066 (17)
C6	0.090 (3)	0.122 (4)	0.087 (3)	−0.046 (3)	0.023 (2)	−0.005 (3)
C7	0.105 (4)	0.172 (6)	0.110 (4)	−0.057 (4)	0.043 (3)	0.012 (4)
C8	0.110 (4)	0.183 (6)	0.088 (4)	−0.026 (4)	0.045 (3)	0.007 (4)
C9	0.111 (4)	0.142 (5)	0.071 (3)	−0.010 (4)	0.028 (3)	−0.014 (3)
C10	0.067 (2)	0.096 (3)	0.061 (2)	−0.006 (2)	0.0141 (18)	−0.010 (2)
C11	0.0572 (18)	0.0539 (17)	0.0546 (18)	−0.0058 (14)	−0.0099 (15)	−0.0023 (14)
C12	0.077 (2)	0.057 (2)	0.062 (2)	−0.0165 (18)	−0.0148 (18)	0.0035 (16)
C13	0.096 (3)	0.052 (2)	0.092 (3)	−0.008 (2)	−0.035 (3)	0.0041 (19)
C14	0.089 (3)	0.067 (3)	0.106 (3)	0.018 (2)	−0.030 (3)	−0.014 (2)
C15	0.083 (3)	0.093 (3)	0.086 (3)	0.030 (2)	0.000 (2)	0.002 (2)
C16	0.072 (2)	0.074 (2)	0.062 (2)	0.0119 (19)	0.0010 (18)	0.0075 (17)
C17	0.0503 (17)	0.0574 (18)	0.0541 (17)	−0.0048 (14)	0.0080 (14)	−0.0067 (14)
C18	0.0544 (19)	0.076 (2)	0.071 (2)	−0.0137 (17)	0.0012 (16)	0.0005 (18)
C19	0.063 (2)	0.090 (3)	0.085 (3)	−0.026 (2)	0.004 (2)	−0.012 (2)
C20	0.101 (3)	0.076 (3)	0.105 (3)	−0.038 (3)	0.012 (3)	−0.008 (3)
C21	0.109 (4)	0.063 (2)	0.143 (5)	−0.025 (3)	−0.024 (3)	0.016 (3)
C22	0.079 (3)	0.061 (2)	0.096 (3)	−0.0155 (19)	−0.011 (2)	0.005 (2)
C23	0.0469 (16)	0.0531 (17)	0.0607 (19)	−0.0063 (13)	0.0032 (14)	−0.0014 (14)
C24	0.0534 (19)	0.095 (3)	0.077 (2)	0.0010 (19)	0.0082 (18)	−0.008 (2)
C25	0.0465 (19)	0.094 (3)	0.096 (3)	−0.0001 (19)	0.0016 (19)	−0.004 (2)
C26	0.056 (2)	0.065 (2)	0.085 (3)	−0.0047 (16)	−0.0183 (18)	−0.0004 (19)
C27	0.063 (2)	0.079 (2)	0.065 (2)	0.0018 (18)	−0.0080 (17)	−0.0002 (18)
C28	0.0518 (18)	0.071 (2)	0.062 (2)	0.0013 (16)	0.0013 (15)	0.0037 (16)
C29	0.0331 (12)	0.0454 (14)	0.0469 (15)	−0.0032 (11)	0.0020 (11)	−0.0006 (12)
C30	0.0348 (13)	0.0587 (17)	0.0494 (16)	−0.0034 (12)	0.0041 (12)	−0.0051 (13)
C31	0.0399 (14)	0.0650 (19)	0.0520 (17)	−0.0042 (13)	−0.0019 (13)	0.0009 (14)
C32	0.0306 (13)	0.0585 (18)	0.069 (2)	−0.0038 (12)	0.0005 (13)	−0.0011 (15)
C33	0.0365 (14)	0.0634 (19)	0.0599 (19)	−0.0062 (13)	0.0134 (13)	−0.0071 (14)
C34	0.0394 (14)	0.0643 (18)	0.0487 (16)	−0.0062 (13)	0.0043 (12)	−0.0005 (14)
C35	0.0295 (12)	0.071 (2)	0.0521 (17)	−0.0027 (13)	0.0025 (12)	−0.0085 (15)
C36	0.0449 (16)	0.072 (2)	0.071 (2)	−0.0025 (15)	0.0037 (15)	−0.0159 (17)
C37	0.0470 (19)	0.104 (3)	0.083 (3)	0.0028 (19)	0.0070 (18)	−0.037 (2)
C38	0.0469 (19)	0.140 (4)	0.058 (2)	−0.009 (2)	0.0088 (16)	−0.025 (3)
C39	0.0489 (18)	0.122 (3)	0.0514 (19)	−0.011 (2)	0.0017 (15)	−0.002 (2)
C40	0.0377 (15)	0.085 (2)	0.0541 (18)	−0.0022 (15)	0.0026 (13)	0.0011 (16)
C41	0.0399 (14)	0.0518 (16)	0.0545 (17)	0.0022 (12)	−0.0009 (12)	−0.0022 (13)
C42	0.0588 (19)	0.0536 (18)	0.076 (2)	−0.0053 (15)	−0.0123 (17)	0.0027 (16)
C43	0.086 (3)	0.056 (2)	0.100 (3)	−0.0090 (19)	−0.011 (2)	0.019 (2)
C44	0.091 (3)	0.070 (2)	0.083 (3)	0.012 (2)	−0.014 (2)	0.014 (2)
C45	0.064 (2)	0.086 (3)	0.077 (3)	0.012 (2)	−0.0208 (19)	0.006 (2)
C46	0.0435 (16)	0.071 (2)	0.075 (2)	−0.0003 (15)	−0.0071 (16)	0.0052 (18)
C47	0.0342 (13)	0.0515 (16)	0.0554 (17)	−0.0028 (12)	−0.0011 (12)	−0.0014 (13)
C48	0.0513 (17)	0.0577 (18)	0.0594 (18)	−0.0017 (14)	0.0090 (14)	0.0051 (15)
C49	0.067 (2)	0.0517 (18)	0.082 (2)	−0.0154 (16)	0.0069 (19)	0.0053 (17)
C50	0.068 (2)	0.0477 (17)	0.079 (2)	−0.0017 (15)	−0.0035 (19)	−0.0047 (16)
C51	0.067 (2)	0.076 (2)	0.073 (2)	−0.0100 (19)	0.0159 (18)	−0.0179 (19)
C52	0.0578 (19)	0.076 (2)	0.068 (2)	−0.0235 (17)	0.0161 (16)	−0.0166 (18)

Zn—S1	2.3346 (10)	C20—C21	1.366 (7)
Zn—S2	2.3340 (10)	C20—H20	0.93
Zn—S4	2.3376 (9)	C21—C22	1.386 (6)
Zn—S5	2.3566 (10)	C21—H21	0.93
S1—C1	1.733 (3)	C22—H22	0.93
S2—C1	1.727 (3)	C23—C28	1.382 (5)
S3—O1	1.421 (3)	C23—C24	1.397 (5)
S3—O2	1.435 (3)	C24—C25	1.375 (5)
S3—N1	1.589 (3)	C24—H24	0.93
S3—C2	1.818 (4)	C25—C26	1.369 (6)
S4—C3	1.735 (3)	C25—H25	0.93
S5—C3	1.730 (3)	C26—C27	1.375 (5)
S6—O3	1.425 (3)	C26—H26	0.93
S6—O4	1.431 (3)	C27—C28	1.386 (5)
S6—N2	1.593 (3)	C27—H27	0.93
S6—C4	1.821 (5)	C28—H28	0.93
P1—C17	1.785 (3)	C29—C30	1.383 (4)
P1—C5	1.790 (4)	C29—C34	1.389 (4)
P1—C23	1.798 (3)	C30—C31	1.391 (4)
P1—C11	1.802 (3)	C30—H30	0.93
P2—C41	1.788 (3)	C31—C32	1.379 (4)
P2—C35	1.793 (3)	C31—H31	0.93
P2—C47	1.799 (3)	C32—C33	1.366 (4)
P2—C29	1.802 (3)	C32—H32	0.93
F1—C2	1.309 (5)	C33—C34	1.383 (4)
F2—C2	1.303 (5)	C33—H33	0.93
F3—C2	1.328 (4)	C34—H34	0.93
F4—C4	1.319 (6)	C35—C36	1.385 (5)
F5—C4	1.323 (5)	C35—C40	1.400 (5)
F6—C4	1.321 (5)	C36—C37	1.399 (5)
N1—C1	1.314 (4)	C36—H36	0.93
N2—C3	1.314 (4)	C37—C38	1.367 (7)
C5—C6	1.383 (5)	C37—H37	0.93
C5—C10	1.386 (5)	C38—C39	1.356 (6)
C6—C7	1.381 (7)	C38—H38	0.93
C6—H6	0.93	C39—C40	1.379 (5)
C7—C8	1.387 (8)	C39—H39	0.93
C7—H7	0.93	C40—H40	0.93
C8—C9	1.356 (8)	C41—C42	1.391 (4)
C8—H8	0.93	C41—C46	1.397 (4)
C9—C10	1.372 (6)	C42—C43	1.382 (5)
C9—H9	0.93	C42—H42	0.93
C10—H10	0.93	C43—C44	1.372 (6)
C11—C12	1.389 (5)	C43—H43	0.93
C11—C16	1.389 (5)	C44—C45	1.373 (6)
C12—C13	1.380 (6)	C44—H44	0.93
C12—H12	0.93	C45—C46	1.377 (5)
C13—C14	1.362 (7)	C45—H45	0.93
C13—H13	0.93	C46—H46	0.93
C14—C15	1.381 (7)	C47—C48	1.381 (4)
C14—H14	0.93	C47—C52	1.389 (4)
C15—C16	1.381 (6)	C48—C49	1.374 (5)
C15—H15	0.93	C48—H48	0.93
C16—H16	0.93	C49—C50	1.366 (5)
C17—C22	1.366 (5)	C49—H49	0.93
C17—C18	1.400 (5)	C50—C51	1.377 (5)
C18—C19	1.383 (5)	C50—H50	0.93
C18—H18	0.93	C51—C52	1.369 (5)
C19—C20	1.362 (7)	C51—H51	0.93
C19—H19	0.93	C52—H52	0.93
S2—Zn—S1	77.84 (3)	C19—C20—C21	120.2 (4)
S2—Zn—S4	128.21 (4)	C19—C20—H20	119.9
S1—Zn—S4	132.48 (4)	C21—C20—H20	119.9
S2—Zn—S5	124.69 (4)	C20—C21—C22	120.1 (4)
S1—Zn—S5	123.49 (4)	C20—C21—H21	119.9
S4—Zn—S5	77.63 (3)	C22—C21—H21	119.9
C1—S1—Zn	83.04 (11)	C17—C22—C21	120.2 (4)
C1—S2—Zn	83.17 (11)	C17—C22—H22	119.9
O1—S3—O2	117.00 (15)	C21—C22—H22	119.9
O1—S3—N1	116.02 (16)	C28—C23—C24	118.8 (3)
O2—S3—N1	113.61 (16)	C28—C23—P1	119.8 (2)
O1—S3—C2	104.9 (2)	C24—C23—P1	121.4 (3)
O2—S3—C2	104.58 (19)	C25—C24—C23	120.0 (4)
N1—S3—C2	97.43 (17)	C25—C24—H24	120
C3—S4—Zn	83.31 (11)	C23—C24—H24	120
C3—S5—Zn	82.82 (11)	C26—C25—C24	121.0 (4)
O3—S6—O4	117.73 (18)	C26—C25—H25	119.5
O3—S6—N2	114.39 (16)	C24—C25—H25	119.5
O4—S6—N2	115.02 (15)	C25—C26—C27	119.6 (3)
O3—S6—C4	105.2 (2)	C25—C26—H26	120.2
O4—S6—C4	104.2 (2)	C27—C26—H26	120.2
N2—S6—C4	96.67 (18)	C26—C27—C28	120.3 (4)
C17—P1—C5	110.23 (16)	C26—C27—H27	119.9
C17—P1—C23	109.44 (15)	C28—C27—H27	119.9
C5—P1—C23	108.09 (16)	C23—C28—C27	120.3 (3)
C17—P1—C11	106.60 (15)	C23—C28—H28	119.8
C5—P1—C11	110.89 (17)	C27—C28—H28	119.8
C23—P1—C11	111.59 (15)	C30—C29—C34	120.1 (3)
C41—P2—C35	109.70 (15)	C30—C29—P2	120.3 (2)
C41—P2—C47	106.90 (14)	C34—C29—P2	119.5 (2)
C35—P2—C47	112.13 (14)	C29—C30—C31	119.9 (3)
C41—P2—C29	111.16 (13)	C29—C30—H30	120.1
C35—P2—C29	107.61 (13)	C31—C30—H30	120.1
C47—P2—C29	109.39 (13)	C32—C31—C30	119.2 (3)
C1—N1—S3	122.3 (2)	C32—C31—H31	120.4
C3—N2—S6	121.9 (2)	C30—C31—H31	120.4
N1—C1—S2	117.5 (2)	C33—C32—C31	121.2 (3)
N1—C1—S1	126.6 (3)	C33—C32—H32	119.4
S2—C1—S1	115.92 (19)	C31—C32—H32	119.4
F2—C2—F1	108.0 (4)	C32—C33—C34	120.1 (3)
F2—C2—F3	108.0 (4)	C32—C33—H33	120
F1—C2—F3	108.0 (4)	C34—C33—H33	120
F2—C2—S3	112.5 (3)	C33—C34—C29	119.6 (3)
F1—C2—S3	111.5 (3)	C33—C34—H34	120.2
F3—C2—S3	108.7 (3)	C29—C34—H34	120.2
N2—C3—S5	125.6 (2)	C36—C35—C40	119.3 (3)
N2—C3—S4	118.1 (2)	C36—C35—P2	119.8 (3)
S5—C3—S4	116.24 (18)	C40—C35—P2	120.8 (2)
F4—C4—F6	107.6 (4)	C35—C36—C37	119.4 (4)
F4—C4—F5	107.6 (4)	C35—C36—H36	120.3
F6—C4—F5	107.6 (4)	C37—C36—H36	120.3
F4—C4—S6	112.5 (3)	C38—C37—C36	120.1 (4)
F6—C4—S6	111.9 (3)	C38—C37—H37	120
F5—C4—S6	109.4 (3)	C36—C37—H37	120
C6—C5—C10	119.5 (4)	C39—C38—C37	120.9 (4)
C6—C5—P1	120.1 (3)	C39—C38—H38	119.5
C10—C5—P1	120.4 (3)	C37—C38—H38	119.5
C7—C6—C5	119.8 (5)	C38—C39—C40	120.5 (4)
C7—C6—H6	120.1	C38—C39—H39	119.8
C5—C6—H6	120.1	C40—C39—H39	119.8
C6—C7—C8	119.7 (5)	C39—C40—C35	119.8 (4)
C6—C7—H7	120.2	C39—C40—H40	120.1
C8—C7—H7	120.2	C35—C40—H40	120.1
C9—C8—C7	120.5 (5)	C42—C41—C46	119.4 (3)
C9—C8—H8	119.8	C42—C41—P2	122.2 (2)
C7—C8—H8	119.8	C46—C41—P2	118.5 (2)
C8—C9—C10	120.3 (5)	C43—C42—C41	119.8 (3)
C8—C9—H9	119.9	C43—C42—H42	120.1
C10—C9—H9	119.9	C41—C42—H42	120.1
C9—C10—C5	120.3 (4)	C44—C43—C42	120.2 (4)
C9—C10—H10	119.9	C44—C43—H43	119.9
C5—C10—H10	119.9	C42—C43—H43	119.9
C12—C11—C16	119.2 (3)	C43—C44—C45	120.3 (4)
C12—C11—P1	121.7 (3)	C43—C44—H44	119.8
C16—C11—P1	119.0 (3)	C45—C44—H44	119.8
C13—C12—C11	119.6 (4)	C44—C45—C46	120.5 (4)
C13—C12—H12	120.2	C44—C45—H45	119.8
C11—C12—H12	120.2	C46—C45—H45	119.8
C14—C13—C12	121.2 (4)	C45—C46—C41	119.7 (3)
C14—C13—H13	119.4	C45—C46—H46	120.2
C12—C13—H13	119.4	C41—C46—H46	120.2
C13—C14—C15	119.7 (4)	C48—C47—C52	119.4 (3)
C13—C14—H14	120.2	C48—C47—P2	123.8 (2)
C15—C14—H14	120.2	C52—C47—P2	116.7 (2)
C14—C15—C16	120.1 (4)	C49—C48—C47	119.7 (3)
C14—C15—H15	119.9	C49—C48—H48	120.2
C16—C15—H15	119.9	C47—C48—H48	120.2
C15—C16—C11	120.2 (4)	C50—C49—C48	120.7 (3)
C15—C16—H16	119.9	C50—C49—H49	119.7
C11—C16—H16	119.9	C48—C49—H49	119.7
C22—C17—C18	119.6 (3)	C49—C50—C51	120.1 (3)
C22—C17—P1	121.8 (3)	C49—C50—H50	120
C18—C17—P1	118.5 (3)	C51—C50—H50	120
C19—C18—C17	119.1 (4)	C52—C51—C50	119.8 (3)
C19—C18—H18	120.5	C52—C51—H51	120.1
C17—C18—H18	120.5	C50—C51—H51	120.1
C20—C19—C18	120.7 (4)	C51—C52—C47	120.3 (3)
C20—C19—H19	119.6	C51—C52—H52	119.9
C18—C19—H19	119.6	C47—C52—H52	119.9
S2—Zn—S1—C1	1.16 (11)	C23—P1—C17—C18	−165.3 (3)
S4—Zn—S1—C1	−130.18 (11)	C11—P1—C17—C18	−44.5 (3)
S5—Zn—S1—C1	124.91 (11)	C22—C17—C18—C19	0.3 (6)
S1—Zn—S2—C1	−1.17 (11)	P1—C17—C18—C19	−178.6 (3)
S4—Zn—S2—C1	134.03 (11)	C17—C18—C19—C20	−0.5 (6)
S5—Zn—S2—C1	−123.66 (11)	C18—C19—C20—C21	0.3 (7)
S2—Zn—S4—C3	123.96 (10)	C19—C20—C21—C22	0.2 (8)
S1—Zn—S4—C3	−125.12 (10)	C18—C17—C22—C21	0.2 (6)
S5—Zn—S4—C3	−0.72 (10)	P1—C17—C22—C21	179.1 (4)
S2—Zn—S5—C3	−127.47 (10)	C20—C21—C22—C17	−0.4 (8)
S1—Zn—S5—C3	133.86 (10)	C17—P1—C23—C28	73.9 (3)
S4—Zn—S5—C3	0.72 (10)	C5—P1—C23—C28	−166.0 (3)
O1—S3—N1—C1	−65.2 (3)	C11—P1—C23—C28	−43.8 (3)
O2—S3—N1—C1	74.6 (3)	C17—P1—C23—C24	−103.9 (3)
C2—S3—N1—C1	−175.9 (3)	C5—P1—C23—C24	16.1 (3)
O3—S6—N2—C3	70.0 (3)	C11—P1—C23—C24	138.3 (3)
O4—S6—N2—C3	−70.8 (3)	C28—C23—C24—C25	1.0 (6)
C4—S6—N2—C3	−180.0 (3)	P1—C23—C24—C25	178.9 (3)
S3—N1—C1—S2	−175.78 (19)	C23—C24—C25—C26	−0.9 (7)
S3—N1—C1—S1	4.8 (5)	C24—C25—C26—C27	−0.1 (6)
Zn—S2—C1—N1	−177.8 (3)	C25—C26—C27—C28	0.9 (6)
Zn—S2—C1—S1	1.71 (16)	C24—C23—C28—C27	−0.2 (5)
Zn—S1—C1—N1	177.7 (3)	P1—C23—C28—C27	−178.1 (3)
Zn—S1—C1—S2	−1.71 (16)	C26—C27—C28—C23	−0.7 (6)
O1—S3—C2—F2	−176.8 (3)	C41—P2—C29—C30	129.3 (2)
O2—S3—C2—F2	59.5 (3)	C35—P2—C29—C30	9.2 (3)
N1—S3—C2—F2	−57.3 (3)	C47—P2—C29—C30	−112.9 (2)
O1—S3—C2—F1	−55.3 (3)	C41—P2—C29—C34	−54.8 (3)
O2—S3—C2—F1	−179.0 (3)	C35—P2—C29—C34	−175.0 (2)
N1—S3—C2—F1	64.2 (3)	C47—P2—C29—C34	63.0 (3)
O1—S3—C2—F3	63.6 (4)	C34—C29—C30—C31	−2.3 (4)
O2—S3—C2—F3	−60.1 (4)	P2—C29—C30—C31	173.6 (2)
N1—S3—C2—F3	−176.9 (3)	C29—C30—C31—C32	1.1 (5)
S6—N2—C3—S5	−0.1 (4)	C30—C31—C32—C33	0.6 (5)
S6—N2—C3—S4	179.99 (16)	C31—C32—C33—C34	−1.2 (5)
Zn—S5—C3—N2	179.0 (3)	C32—C33—C34—C29	0.0 (5)
Zn—S5—C3—S4	−1.06 (15)	C30—C29—C34—C33	1.7 (5)
Zn—S4—C3—N2	−179.0 (2)	P2—C29—C34—C33	−174.2 (2)
Zn—S4—C3—S5	1.07 (15)	C41—P2—C35—C36	−10.6 (3)
O3—S6—C4—F4	178.5 (3)	C47—P2—C35—C36	−129.2 (2)
O4—S6—C4—F4	−57.0 (3)	C29—P2—C35—C36	110.5 (3)
N2—S6—C4—F4	61.0 (3)	C41—P2—C35—C40	172.0 (2)
O3—S6—C4—F6	57.3 (4)	C47—P2—C35—C40	53.3 (3)
O4—S6—C4—F6	−178.3 (3)	C29—P2—C35—C40	−67.0 (3)
N2—S6—C4—F6	−60.3 (4)	C40—C35—C36—C37	−0.5 (5)
O3—S6—C4—F5	−62.0 (4)	P2—C35—C36—C37	−178.0 (3)
O4—S6—C4—F5	62.5 (4)	C35—C36—C37—C38	−1.1 (5)
N2—S6—C4—F5	−179.5 (3)	C36—C37—C38—C39	1.9 (6)
C17—P1—C5—C6	174.8 (4)	C37—C38—C39—C40	−1.1 (6)
C23—P1—C5—C6	55.3 (4)	C38—C39—C40—C35	−0.6 (5)
C11—P1—C5—C6	−67.4 (4)	C36—C35—C40—C39	1.3 (5)
C17—P1—C5—C10	−2.4 (4)	P2—C35—C40—C39	178.8 (2)
C23—P1—C5—C10	−122.0 (3)	C35—P2—C41—C42	102.1 (3)
C11—P1—C5—C10	115.4 (3)	C47—P2—C41—C42	−136.1 (3)
C10—C5—C6—C7	0.8 (8)	C29—P2—C41—C42	−16.8 (3)
P1—C5—C6—C7	−176.5 (5)	C35—P2—C41—C46	−78.2 (3)
C5—C6—C7—C8	0.9 (10)	C47—P2—C41—C46	43.6 (3)
C6—C7—C8—C9	−2.9 (11)	C29—P2—C41—C46	162.9 (3)
C7—C8—C9—C10	3.1 (10)	C46—C41—C42—C43	0.2 (5)
C8—C9—C10—C5	−1.3 (8)	P2—C41—C42—C43	179.9 (3)
C6—C5—C10—C9	−0.7 (7)	C41—C42—C43—C44	1.1 (6)
P1—C5—C10—C9	176.6 (4)	C42—C43—C44—C45	−0.7 (7)
C17—P1—C11—C12	131.2 (3)	C43—C44—C45—C46	−1.1 (7)
C5—P1—C11—C12	11.2 (3)	C44—C45—C46—C41	2.5 (6)
C23—P1—C11—C12	−109.4 (3)	C42—C41—C46—C45	−2.0 (5)
C17—P1—C11—C16	−45.4 (3)	P2—C41—C46—C45	178.3 (3)
C5—P1—C11—C16	−165.4 (3)	C41—P2—C47—C48	−124.1 (3)
C23—P1—C11—C16	74.1 (3)	C35—P2—C47—C48	−3.9 (3)
C16—C11—C12—C13	0.3 (5)	C29—P2—C47—C48	115.4 (3)
P1—C11—C12—C13	−176.2 (3)	C41—P2—C47—C52	55.2 (3)
C11—C12—C13—C14	−0.3 (6)	C35—P2—C47—C52	175.4 (3)
C12—C13—C14—C15	−0.4 (6)	C29—P2—C47—C52	−65.3 (3)
C13—C14—C15—C16	1.2 (7)	C52—C47—C48—C49	0.7 (5)
C14—C15—C16—C11	−1.2 (7)	P2—C47—C48—C49	179.9 (3)
C12—C11—C16—C15	0.4 (5)	C47—C48—C49—C50	0.6 (5)
P1—C11—C16—C15	177.1 (3)	C48—C49—C50—C51	−0.9 (6)
C5—P1—C17—C22	−103.0 (3)	C49—C50—C51—C52	−0.1 (6)
C23—P1—C17—C22	15.8 (4)	C50—C51—C52—C47	1.4 (6)
C11—P1—C17—C22	136.6 (3)	C48—C47—C52—C51	−1.7 (5)
C5—P1—C17—C18	75.9 (3)	P2—C47—C52—C51	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.68	3.424 (4)	138.
C31—H31···O4	0.93	2.62	3.470 (4)	153.
C33—H33···O2i	0.93	2.47	3.283 (4)	145.

Zn—S1	2.3346 (10)
Zn—S2	2.3340 (10)
Zn—S4	2.3376 (9)
Zn—S5	2.3566 (10)

S2—Zn—S1	77.84 (3)
S4—Zn—S5	77.63 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1	0.93	2.68	3.424 (4)	138
C31—H31⋯O4	0.93	2.62	3.470 (4)	153
C33—H33⋯O2i	0.93	2.47	3.283 (4)	145

Symmetry code: (i) .