The first dinuclear zinc(II) di­thio­carbamate complex with butyl substituent groups

The crystal structure of the title compound, bis(μ-N,N-di­butyl­di­thio­carbamato-κ²S:S′)­bis­[(N,N-di­butyl­di­thio­carbamato-κ²S,S′)­zinc(II)], [Zn₂(C₉H₁₈NS₂)₄], has been determined at 180 K. The structure contains two crystallographically unique Zn²⁺ metal centres, showing almost identical slightly distorted tetrahedral coordination environments, and forming a dinuclear complex with two skew-bridging syn-N,N-di­butyl­di­thio­carbamate ligands. Two other di­thio­carbamate ligands are connected to the Zn²⁺ centres in a syn,syn-chelate coordination mode.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.066
• wR factor = 0.196
• Data-to-parameter ratio = 27.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.87 Ratio

Author Response: After several recrystallisation attempts, the crystal chosen for X-ray diffraction analysis was a very small block (dimensions of 0.14x0.12x0.10 mm) of average quality. Although the collected data set was not ideal, structure solution and refinement proceeded routinely, with the exception of some C atoms. These are severely affected by thermal disorder and failed to refine successfully with anisotropic displacement parameters (see Experimental Section). Attempts were made to model the disorder along the alkyl chains of the substituent groups, but little progress was made in achieving a better refinement convergence than that given in this communication.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.29 Ratio

Author Response: Please, see response to _vrf_PLAT220_I.

Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ..... =         10
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C34
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H18B   ..  H25B     =       2.07 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         S6
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C35
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C12
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C16
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C17
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C26
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

   2 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

bis(µ-N,N-dibutyldithiocarbamato- κ²S:S')bis[(N,N-dibutyldithiocarbamato-κ²S,S')zinc(II)]

Crystal data

[Zn2(C9H18NS2)4]	F(000) = 2016
Mr = 948.20	Dx = 1.285 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 22557 reflections
a = 16.036 (3) Å	θ = 1.0–27.5°
b = 16.604 (3) Å	µ = 1.35 mm^−1
c = 18.487 (4) Å	T = 180 K
β = 95.10 (3)°	Block, colourless
V = 4902.7 (17) Å^3	0.14 × 0.12 × 0.10 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	7744 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Thin–slice ω and φ scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (Sortav; Blessing, 1995)	h = −20→20
Tmin = 0.748, Tmax = 0.877	k = −20→21
30156 measured reflections	l = −18→23
11123 independent reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0737P)^2 + 11.7125P] where P = (Fo^2 + 2Fc^2)/3
11123 reflections	(Δ/σ)max < 0.001
409 parameters	Δρmax = 1.64 e Å^−3
50 restraints	Δρmin = −0.86 e Å^−3

Special details

Experimental. Zn atoms directly located from Patterson synthesis. The remaining atoms were located from consecutive difference Fourier map syntheses.

Although all the C-atoms from the butyl substituent groups were easily found in difference Fourier maps, they are severely affected by thermal disorder, which is reflected in large U_eq when isotropic displacements are considered. Anisotropic treatment for these atoms results in large adps for some of them. Common/independent isotropic displacement parameters were used for the following C-atoms: 1 - C24 2 - C25 3 - C8 C17 C26 C35 4 - C9 C27 C38

The C18 atom was found to be disordered over two different positions. This was modelled with partial occupancies of 60 and 40% for C18 and C18', respectively.

The –CH2—CH2—CH2—CH3 chains were also refined with bond length restraints (C–C distance of 1.52 A, plus a geometrical restraint for the C···C···C distance associated with the refined C–C bond length).

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.29406 (3)	0.91781 (3)	0.60034 (3)	0.04816 (16)
Zn2	0.21360 (3)	0.92350 (3)	0.40513 (3)	0.04807 (16)
S1	0.36961 (7)	0.79986 (7)	0.63130 (7)	0.0516 (3)
S2	0.29278 (8)	0.90940 (8)	0.73182 (7)	0.0580 (3)
N1	0.3705 (2)	0.7727 (2)	0.7738 (2)	0.0543 (10)
C1	0.3473 (3)	0.8222 (3)	0.7192 (3)	0.0485 (10)
C2	0.4198 (3)	0.6993 (3)	0.7629 (3)	0.0598 (13)
H2A	0.4035	0.6776	0.7138	0.072*
H2B	0.4059	0.6581	0.7987	0.072*
C3	0.5135 (3)	0.7138 (3)	0.7708 (3)	0.0636 (14)
H3A	0.5267	0.7595	0.7394	0.076*
H3B	0.5310	0.7290	0.8217	0.076*
C4	0.5629 (3)	0.6414 (3)	0.7510 (3)	0.0696 (15)
H4A	0.5459	0.6262	0.7000	0.084*
H4B	0.5498	0.5956	0.7823	0.084*
C5	0.6572 (3)	0.6569 (4)	0.7596 (4)	0.089 (2)
H5A	0.6869	0.6083	0.7462	0.133*
H5B	0.6745	0.6709	0.8102	0.133*
H5C	0.6706	0.7015	0.7279	0.133*
C6	0.3479 (3)	0.7896 (4)	0.8479 (3)	0.0739 (17)
H6A	0.3464	0.7382	0.8749	0.089*
H6B	0.2909	0.8130	0.8448	0.089*
C7	0.4078 (4)	0.8470 (5)	0.8905 (3)	0.100 (2)
H7A	0.4098	0.8995	0.8654	0.120*
H7B	0.4650	0.8241	0.8964	0.120*
C8	0.3725 (7)	0.8572 (7)	0.9652 (5)	0.152 (2)*
H8A	0.3125	0.8721	0.9583	0.183*
H8B	0.3775	0.8058	0.9925	0.183*
C9	0.4202 (8)	0.9210 (8)	1.0065 (7)	0.205 (3)*
H9A	0.4258	0.9071	1.0582	0.307*
H9B	0.3905	0.9724	0.9996	0.307*
H9C	0.4760	0.9258	0.9890	0.307*
S3	0.15428 (7)	0.90073 (8)	0.55006 (6)	0.0514 (3)
S4	0.14958 (8)	1.03786 (8)	0.44524 (6)	0.0529 (3)
N2	0.0861 (2)	1.0451 (3)	0.5724 (2)	0.0605 (11)
C10	0.1264 (2)	1.0006 (3)	0.5280 (2)	0.0475 (10)
C11	0.0615 (3)	1.0165 (4)	0.6426 (3)	0.0736 (17)
H11A	0.0644	0.9570	0.6436	0.088*
H11B	0.0025	1.0320	0.6470	0.088*
C12	0.1155 (3)	1.0495 (3)	0.7076 (2)	0.0580 (12)
H12A	0.1745	1.0339	0.7039	0.070*
H12B	0.1125	1.1091	0.7074	0.070*
C13	0.0872 (4)	1.0180 (4)	0.7781 (3)	0.0799 (17)
H13A	0.0902	0.9585	0.7783	0.096*
H13B	0.0280	1.0336	0.7816	0.096*
C14	0.1405 (5)	1.0507 (5)	0.8433 (3)	0.098 (2)
H14A	0.1197	1.0298	0.8880	0.147*
H14B	0.1376	1.1097	0.8433	0.147*
H14C	0.1987	1.0337	0.8409	0.147*
C15	0.0595 (3)	1.1277 (3)	0.5516 (4)	0.0827 (19)
H15A	0.0096	1.1422	0.5767	0.099*
H15B	0.0437	1.1297	0.4987	0.099*
C16	0.1290 (4)	1.1890 (4)	0.5712 (4)	0.093 (2)
H16A	0.1478	1.1853	0.6236	0.111*
H16B	0.1776	1.1780	0.5432	0.111*
C17	0.0946 (7)	1.2717 (5)	0.5534 (6)	0.152 (2)*
H17A	0.0435	1.2806	0.5787	0.183*	0.600 (13)
H17B	0.1365	1.3129	0.5707	0.183*	0.600 (13)
H17C	0.0854	1.2748	0.4998	0.183*	0.400 (13)
H17D	0.0386	1.2741	0.5719	0.183*	0.400 (13)
C18	0.0743 (14)	1.2808 (12)	0.4746 (8)	0.205 (3)*	0.600 (13)
H18A	0.0827	1.3369	0.4606	0.307*	0.600 (13)
H18B	0.0158	1.2656	0.4619	0.307*	0.600 (13)
H18C	0.1109	1.2458	0.4487	0.307*	0.600 (13)
C18'	0.1386 (18)	1.3465 (10)	0.5776 (18)	0.205 (3)*	0.400 (13)
H18D	0.1197	1.3909	0.5453	0.307*	0.400 (13)
H18E	0.1991	1.3391	0.5763	0.307*	0.400 (13)
H18F	0.1262	1.3591	0.6273	0.307*	0.400 (13)
S5	0.13939 (7)	0.80851 (7)	0.36401 (7)	0.0517 (3)
S6	0.21634 (10)	0.92856 (10)	0.27351 (7)	0.0713 (4)
N3	0.1360 (3)	0.7976 (3)	0.2199 (2)	0.0699 (13)
C19	0.1602 (3)	0.8406 (3)	0.2788 (3)	0.0541 (11)
C20	0.0846 (3)	0.7250 (4)	0.2236 (3)	0.0711 (16)
H20A	0.1012	0.6964	0.2696	0.085*
H20B	0.0956	0.6887	0.1831	0.085*
C21	−0.0091 (3)	0.7432 (3)	0.2197 (3)	0.0676 (15)
H21A	−0.0204	0.7792	0.2604	0.081*
H21B	−0.0259	0.7719	0.1737	0.081*
C22	−0.0610 (3)	0.6681 (3)	0.2233 (4)	0.0799 (19)
H22A	−0.0448	0.6400	0.2696	0.096*
H22B	−0.0486	0.6316	0.1832	0.096*
C23	−0.1544 (3)	0.6852 (4)	0.2177 (4)	0.091 (2)
H23A	−0.1849	0.6352	0.2255	0.137*
H23B	−0.1721	0.7067	0.1694	0.137*
H23C	−0.1664	0.7247	0.2548	0.137*
C24	0.1639 (5)	0.8206 (5)	0.1451 (4)	0.099 (2)*
H24A	0.2215	0.8428	0.1505	0.119*
H24B	0.1635	0.7725	0.1134	0.119*
C25	0.1037 (6)	0.8827 (5)	0.1123 (5)	0.133 (3)*
H25A	0.0917	0.9224	0.1500	0.160*
H25B	0.0503	0.8562	0.0950	0.160*
C26	0.1396 (7)	0.9278 (6)	0.0470 (5)	0.152 (2)*
H26A	0.1021	0.9722	0.0290	0.183*
H26B	0.1959	0.9500	0.0614	0.183*
C27	0.1434 (9)	0.8639 (8)	−0.0088 (6)	0.205 (3)*
H27A	0.1684	0.8859	−0.0511	0.307*
H27B	0.0867	0.8446	−0.0236	0.307*
H27C	0.1777	0.8190	0.0115	0.307*
S7	0.35428 (7)	0.91066 (7)	0.45436 (6)	0.0467 (3)
S8	0.35135 (7)	1.03892 (7)	0.56711 (6)	0.0476 (3)
N4	0.4115 (2)	1.0613 (2)	0.4403 (2)	0.0451 (8)
C28	0.3752 (2)	1.0098 (3)	0.4820 (2)	0.0423 (9)
C29	0.4376 (3)	1.0404 (3)	0.3679 (2)	0.0522 (11)
H29A	0.4374	0.9811	0.3627	0.063*
H29B	0.4957	1.0593	0.3647	0.063*
C30	0.3818 (3)	1.0766 (3)	0.3058 (2)	0.0483 (10)
H30A	0.3835	1.1361	0.3095	0.058*
H30B	0.3233	1.0591	0.3093	0.058*
C31	0.4099 (4)	1.0507 (3)	0.2328 (2)	0.0657 (14)
H31A	0.4089	0.9912	0.2297	0.079*
H31B	0.4683	1.0687	0.2294	0.079*
C32	0.3543 (4)	1.0855 (4)	0.1692 (3)	0.0823 (18)
H32A	0.3762	1.0697	0.1235	0.123*
H32B	0.3536	1.1444	0.1729	0.123*
H32C	0.2972	1.0647	0.1704	0.123*
C33	0.4305 (3)	1.1448 (3)	0.4642 (3)	0.0538 (11)
H33A	0.4763	1.1659	0.4370	0.065*
H33B	0.4507	1.1442	0.5164	0.065*
C34	0.3561 (3)	1.2012 (3)	0.4531 (3)	0.0573 (12)
H34A	0.3362	1.2029	0.4008	0.069*
H34B	0.3099	1.1804	0.4799	0.069*
C35	0.3788 (6)	1.2846 (5)	0.4790 (6)	0.152 (2)*
H35A	0.4299	1.3016	0.4567	0.183*
H35B	0.3928	1.2828	0.5322	0.183*
C36	0.3120 (8)	1.3472 (7)	0.4624 (7)	0.205 (3)*
H36A	0.3300	1.3983	0.4853	0.307*
H36B	0.2599	1.3295	0.4813	0.307*
H36C	0.3027	1.3547	0.4097	0.307*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0409 (3)	0.0541 (3)	0.0481 (3)	0.0058 (2)	−0.0039 (2)	0.0090 (2)
Zn2	0.0443 (3)	0.0506 (3)	0.0480 (3)	0.0000 (2)	−0.0031 (2)	−0.0063 (2)
S1	0.0466 (6)	0.0512 (6)	0.0558 (7)	0.0066 (5)	−0.0012 (5)	0.0047 (5)
S2	0.0589 (7)	0.0676 (8)	0.0469 (6)	0.0171 (6)	0.0018 (5)	0.0093 (6)
N1	0.042 (2)	0.059 (2)	0.062 (2)	−0.0004 (17)	0.0002 (17)	0.022 (2)
C1	0.035 (2)	0.055 (3)	0.055 (3)	−0.0017 (19)	−0.0029 (18)	0.012 (2)
C2	0.045 (2)	0.054 (3)	0.079 (3)	−0.001 (2)	−0.005 (2)	0.027 (3)
C3	0.043 (3)	0.063 (3)	0.082 (4)	−0.002 (2)	−0.008 (2)	0.018 (3)
C4	0.054 (3)	0.067 (3)	0.087 (4)	0.005 (3)	−0.003 (3)	0.024 (3)
C5	0.053 (3)	0.098 (5)	0.115 (5)	0.012 (3)	0.006 (3)	0.041 (4)
C6	0.062 (3)	0.096 (4)	0.064 (3)	0.005 (3)	0.011 (3)	0.035 (3)
C7	0.078 (4)	0.148 (7)	0.071 (4)	0.021 (5)	−0.005 (3)	0.006 (4)
S3	0.0392 (5)	0.0671 (7)	0.0474 (6)	−0.0025 (5)	0.0004 (4)	0.0068 (5)
S4	0.0555 (7)	0.0548 (7)	0.0458 (6)	0.0137 (5)	−0.0100 (5)	−0.0012 (5)
N2	0.0327 (18)	0.077 (3)	0.072 (3)	−0.0068 (19)	0.0048 (18)	−0.032 (2)
C10	0.0290 (19)	0.065 (3)	0.047 (2)	0.0006 (19)	−0.0076 (16)	−0.009 (2)
C11	0.043 (3)	0.105 (5)	0.075 (4)	−0.026 (3)	0.019 (2)	−0.040 (3)
C12	0.041 (2)	0.060 (3)	0.072 (3)	0.004 (2)	−0.001 (2)	−0.015 (2)
C13	0.080 (4)	0.085 (4)	0.075 (4)	−0.010 (3)	0.014 (3)	−0.026 (3)
C14	0.115 (6)	0.109 (6)	0.067 (4)	0.005 (5)	−0.003 (4)	−0.006 (4)
C15	0.048 (3)	0.079 (4)	0.125 (5)	0.006 (3)	0.022 (3)	−0.037 (4)
C16	0.107 (5)	0.081 (4)	0.090 (5)	−0.022 (4)	0.010 (4)	−0.024 (4)
S5	0.0429 (6)	0.0537 (7)	0.0576 (7)	−0.0048 (5)	0.0006 (5)	−0.0049 (5)
S6	0.0837 (10)	0.0822 (10)	0.0475 (7)	−0.0286 (8)	0.0037 (6)	−0.0029 (6)
N3	0.062 (3)	0.089 (3)	0.059 (3)	−0.011 (2)	0.002 (2)	−0.023 (2)
C19	0.044 (2)	0.065 (3)	0.054 (3)	−0.006 (2)	0.002 (2)	−0.014 (2)
C20	0.048 (3)	0.082 (4)	0.083 (4)	−0.008 (3)	0.001 (3)	−0.040 (3)
C21	0.050 (3)	0.076 (4)	0.074 (4)	0.005 (3)	−0.010 (2)	−0.017 (3)
C22	0.045 (3)	0.081 (4)	0.112 (5)	−0.003 (3)	−0.004 (3)	−0.046 (4)
C23	0.044 (3)	0.110 (5)	0.117 (6)	−0.001 (3)	−0.002 (3)	−0.044 (4)
S7	0.0413 (5)	0.0478 (6)	0.0505 (6)	0.0070 (5)	0.0022 (4)	−0.0016 (5)
S8	0.0501 (6)	0.0500 (6)	0.0411 (6)	−0.0003 (5)	−0.0046 (4)	0.0002 (5)
N4	0.0341 (17)	0.050 (2)	0.050 (2)	0.0041 (15)	−0.0012 (15)	0.0100 (17)
C28	0.0273 (18)	0.053 (2)	0.044 (2)	0.0070 (17)	−0.0083 (16)	0.0050 (19)
C29	0.043 (2)	0.060 (3)	0.054 (3)	0.010 (2)	0.010 (2)	0.013 (2)
C30	0.046 (2)	0.049 (2)	0.050 (3)	−0.0019 (19)	0.0048 (19)	0.009 (2)
C31	0.077 (4)	0.065 (3)	0.057 (3)	0.001 (3)	0.019 (3)	0.006 (3)
C32	0.113 (5)	0.081 (4)	0.051 (3)	−0.008 (4)	0.000 (3)	0.003 (3)
C33	0.043 (2)	0.057 (3)	0.061 (3)	−0.005 (2)	−0.004 (2)	0.008 (2)
C34	0.054 (3)	0.049 (3)	0.066 (3)	0.000 (2)	−0.010 (2)	−0.001 (2)

Geometric parameters (Å, º)

Zn1—S8	2.3164 (14)	C17—H17D	0.990
Zn1—S1	2.3468 (13)	C18—H18A	0.980
Zn1—S3	2.3659 (13)	C18—H18B	0.980
Zn1—S2	2.4365 (14)	C18—H18C	0.980
Zn2—S4	2.3118 (14)	C18'—H18D	0.980
Zn2—S5	2.3406 (13)	C18'—H18E	0.980
Zn2—S7	2.3660 (13)	C18'—H18F	0.980
Zn2—S6	2.4390 (16)	S5—C19	1.723 (5)
S1—C1	1.734 (5)	S6—C19	1.723 (5)
S2—C1	1.719 (5)	N3—C19	1.332 (6)
N1—C1	1.329 (5)	N3—C20	1.466 (7)
N1—C6	1.475 (7)	N3—C24	1.539 (8)
N1—C2	1.476 (6)	C20—C21	1.528 (6)
C2—C3	1.517 (5)	C20—H20A	0.990
C2—H2A	0.990	C20—H20B	0.990
C2—H2B	0.990	C21—C22	1.504 (6)
C3—C4	1.503 (6)	C21—H21A	0.990
C3—H3A	0.990	C21—H21B	0.990
C3—H3B	0.990	C22—C23	1.519 (6)
C4—C5	1.528 (6)	C22—H22A	0.990
C4—H4A	0.990	C22—H22B	0.990
C4—H4B	0.990	C23—H23A	0.980
C5—H5A	0.980	C23—H23B	0.980
C5—H5B	0.980	C23—H23C	0.980
C5—H5C	0.980	C24—C25	1.504 (7)
C6—C7	1.522 (7)	C24—H24A	0.990
C6—H6A	0.990	C24—H24B	0.990
C6—H6B	0.990	C25—C26	1.571 (8)
C7—C8	1.548 (8)	C25—H25A	0.990
C7—H7A	0.990	C25—H25B	0.990
C7—H7B	0.990	C26—C27	1.486 (8)
C8—C9	1.479 (17)	C26—H26A	0.990
C8—H8A	0.990	C26—H26B	0.990
C8—H8B	0.990	C27—H27A	0.980
C9—H9A	0.980	C27—H27B	0.980
C9—H9B	0.980	C27—H27C	0.980
C9—H9C	0.980	S7—C28	1.747 (5)
S3—C10	1.755 (5)	S8—C28	1.722 (4)
S4—C10	1.722 (5)	N4—C28	1.320 (5)
N2—C10	1.316 (6)	N4—C33	1.477 (6)
N2—C11	1.468 (7)	N4—C29	1.479 (6)
N2—C15	1.478 (8)	C29—C30	1.515 (5)
C11—C12	1.520 (5)	C29—H29A	0.990
C11—H11A	0.990	C29—H29B	0.990
C11—H11B	0.990	C30—C31	1.523 (6)
C12—C13	1.510 (6)	C30—H30A	0.990
C12—H12A	0.990	C30—H30B	0.990
C12—H12B	0.990	C31—C32	1.524 (6)
C13—C14	1.516 (6)	C31—H31A	0.990
C13—H13A	0.990	C31—H31B	0.990
C13—H13B	0.990	C32—H32A	0.980
C14—H14A	0.980	C32—H32B	0.980
C14—H14B	0.980	C32—H32C	0.980
C14—H14C	0.980	C33—C34	1.516 (5)
C15—C16	1.528 (6)	C33—H33A	0.990
C15—H15A	0.990	C33—H33B	0.990
C15—H15B	0.990	C34—C35	1.500 (7)
C16—C17	1.507 (8)	C34—H34A	0.990
C16—H16A	0.990	C34—H34B	0.990
C16—H16B	0.990	C35—C36	1.505 (8)
C17—C18	1.472 (9)	C35—H35A	0.990
C17—C18'	1.477 (10)	C35—H35B	0.990
C17—H17A	0.990	C36—H36A	0.980
C17—H17B	0.990	C36—H36B	0.980
C17—H17C	0.990	C36—H36C	0.980
S8—Zn1—S1	125.51 (5)	C18'—C17—H17D	106.6
S8—Zn1—S3	112.59 (5)	C16—C17—H17D	106.6
S1—Zn1—S3	116.50 (5)	H17B—C17—H17D	118.1
S8—Zn1—S2	110.67 (5)	H17C—C17—H17D	106.5
S1—Zn1—S2	76.05 (5)	C17—C18—H18A	109.5
S3—Zn1—S2	107.05 (5)	C17—C18—H18B	109.5
S4—Zn2—S5	123.14 (5)	C17—C18—H18C	109.5
S4—Zn2—S7	112.71 (5)	C17—C18'—H18D	109.5
S5—Zn2—S7	119.42 (5)	C17—C18'—H18E	109.5
S4—Zn2—S6	109.85 (6)	H18D—C18'—H18E	109.5
S5—Zn2—S6	75.99 (5)	C17—C18'—H18F	109.5
S7—Zn2—S6	106.59 (6)	H18D—C18'—H18F	109.5
C1—S1—Zn1	84.57 (15)	H18E—C18'—H18F	109.5
C1—S2—Zn1	82.13 (16)	C19—S5—Zn2	84.85 (16)
C1—N1—C6	120.8 (4)	C19—S6—Zn2	81.83 (17)
C1—N1—C2	121.6 (4)	C19—N3—C20	121.7 (5)
C6—N1—C2	117.6 (4)	C19—N3—C24	121.0 (5)
N1—C1—S2	121.9 (4)	C20—N3—C24	117.2 (5)
N1—C1—S1	120.9 (4)	N3—C19—S6	121.6 (4)
S2—C1—S1	117.2 (3)	N3—C19—S5	121.1 (4)
N1—C2—C3	113.2 (4)	S6—C19—S5	117.3 (3)
N1—C2—H2A	108.9	N3—C20—C21	113.0 (5)
C3—C2—H2A	108.9	N3—C20—H20A	109.0
N1—C2—H2B	108.9	C21—C20—H20A	109.0
C3—C2—H2B	108.9	N3—C20—H20B	109.0
H2A—C2—H2B	107.8	C21—C20—H20B	109.0
C4—C3—C2	112.8 (4)	H20A—C20—H20B	107.8
C4—C3—H3A	109.0	C22—C21—C20	112.3 (4)
C2—C3—H3A	109.0	C22—C21—H21A	109.2
C4—C3—H3B	109.0	C20—C21—H21A	109.2
C2—C3—H3B	109.0	C22—C21—H21B	109.2
H3A—C3—H3B	107.8	C20—C21—H21B	109.2
C3—C4—C5	112.2 (5)	H21A—C21—H21B	107.9
C3—C4—H4A	109.2	C21—C22—C23	112.8 (5)
C5—C4—H4A	109.2	C21—C22—H22A	109.0
C3—C4—H4B	109.2	C23—C22—H22A	109.0
C5—C4—H4B	109.2	C21—C22—H22B	109.0
H4A—C4—H4B	107.9	C23—C22—H22B	109.0
C4—C5—H5A	109.5	H22A—C22—H22B	107.8
C4—C5—H5B	109.5	C22—C23—H23A	109.5
H5A—C5—H5B	109.5	C22—C23—H23B	109.5
C4—C5—H5C	109.5	H23A—C23—H23B	109.5
H5A—C5—H5C	109.5	C22—C23—H23C	109.5
H5B—C5—H5C	109.5	H23A—C23—H23C	109.5
N1—C6—C7	113.9 (4)	H23B—C23—H23C	109.5
N1—C6—H6A	108.8	C25—C24—N3	107.7 (6)
C7—C6—H6A	108.8	C25—C24—H24A	110.2
N1—C6—H6B	108.8	N3—C24—H24A	110.2
C7—C6—H6B	108.8	C25—C24—H24B	110.2
H6A—C6—H6B	107.7	N3—C24—H24B	110.2
C6—C7—C8	105.4 (6)	H24A—C24—H24B	108.5
C6—C7—H7A	110.7	C24—C25—C26	111.7 (7)
C8—C7—H7A	110.7	C24—C25—H25A	109.3
C6—C7—H7B	110.7	C26—C25—H25A	109.3
C8—C7—H7B	110.7	C24—C25—H25B	109.3
H7A—C7—H7B	108.8	C26—C25—H25B	109.3
C9—C8—C7	109.0 (8)	H25A—C25—H25B	107.9
C9—C8—H8A	109.9	C27—C26—C25	103.5 (8)
C7—C8—H8A	109.9	C27—C26—H26A	111.1
C9—C8—H8B	109.9	C25—C26—H26A	111.1
C7—C8—H8B	109.9	C27—C26—H26B	111.1
H8A—C8—H8B	108.3	C25—C26—H26B	111.1
C8—C9—H9A	109.5	H26A—C26—H26B	109.0
C8—C9—H9B	109.5	C26—C27—H27A	109.5
H9A—C9—H9B	109.5	C26—C27—H27B	109.5
C8—C9—H9C	109.5	H27A—C27—H27B	109.5
H9A—C9—H9C	109.5	C26—C27—H27C	109.5
H9B—C9—H9C	109.5	H27A—C27—H27C	109.5
C10—S3—Zn1	101.00 (14)	H27B—C27—H27C	109.5
C10—S4—Zn2	97.28 (16)	C28—S7—Zn2	100.33 (13)
C10—N2—C11	123.7 (5)	C28—S8—Zn1	97.14 (16)
C10—N2—C15	120.4 (5)	C28—N4—C33	121.6 (4)
C11—N2—C15	115.8 (4)	C28—N4—C29	123.4 (4)
N2—C10—S4	120.6 (4)	C33—N4—C29	115.0 (4)
N2—C10—S3	121.0 (4)	N4—C28—S8	119.8 (3)
S4—C10—S3	118.4 (3)	N4—C28—S7	121.6 (3)
N2—C11—C12	113.8 (4)	S8—C28—S7	118.6 (3)
N2—C11—H11A	108.8	N4—C29—C30	113.4 (3)
C12—C11—H11A	108.8	N4—C29—H29A	108.9
N2—C11—H11B	108.8	C30—C29—H29A	108.9
C12—C11—H11B	108.8	N4—C29—H29B	108.9
H11A—C11—H11B	107.7	C30—C29—H29B	108.9
C13—C12—C11	111.3 (4)	H29A—C29—H29B	107.7
C13—C12—H12A	109.4	C29—C30—C31	111.0 (4)
C11—C12—H12A	109.4	C29—C30—H30A	109.4
C13—C12—H12B	109.4	C31—C30—H30A	109.4
C11—C12—H12B	109.4	C29—C30—H30B	109.4
H12A—C12—H12B	108.0	C31—C30—H30B	109.4
C12—C13—C14	111.8 (5)	H30A—C30—H30B	108.0
C12—C13—H13A	109.3	C30—C31—C32	112.2 (4)
C14—C13—H13A	109.3	C30—C31—H31A	109.2
C12—C13—H13B	109.3	C32—C31—H31A	109.2
C14—C13—H13B	109.3	C30—C31—H31B	109.2
H13A—C13—H13B	107.9	C32—C31—H31B	109.2
C13—C14—H14A	109.5	H31A—C31—H31B	107.9
C13—C14—H14B	109.5	C31—C32—H32A	109.5
H14A—C14—H14B	109.5	C31—C32—H32B	109.5
C13—C14—H14C	109.5	H32A—C32—H32B	109.5
H14A—C14—H14C	109.5	C31—C32—H32C	109.5
H14B—C14—H14C	109.5	H32A—C32—H32C	109.5
N2—C15—C16	111.7 (5)	H32B—C32—H32C	109.5
N2—C15—H15A	109.3	N4—C33—C34	113.6 (4)
C16—C15—H15A	109.3	N4—C33—H33A	108.9
N2—C15—H15B	109.3	C34—C33—H33A	108.9
C16—C15—H15B	109.3	N4—C33—H33B	108.9
H15A—C15—H15B	108.0	C34—C33—H33B	108.9
C17—C16—C15	108.1 (6)	H33A—C33—H33B	107.7
C17—C16—H16A	110.1	C35—C34—C33	111.2 (5)
C15—C16—H16A	110.1	C35—C34—H34A	109.4
C17—C16—H16B	110.1	C33—C34—H34A	109.4
C15—C16—H16B	110.1	C35—C34—H34B	109.4
H16A—C16—H16B	108.4	C33—C34—H34B	109.4
C18—C17—C18'	105.8 (17)	H34A—C34—H34B	108.0
C18—C17—C16	110.7 (10)	C34—C35—C36	115.1 (8)
C18'—C17—C16	123.0 (12)	C34—C35—H35A	108.5
C18—C17—H17A	109.5	C36—C35—H35A	108.5
C18'—C17—H17A	97.2	C34—C35—H35B	108.5
C16—C17—H17A	109.5	C36—C35—H35B	108.5
C18—C17—H17B	109.5	H35A—C35—H35B	107.5
C16—C17—H17B	109.5	C35—C36—H36A	109.5
H17A—C17—H17B	108.1	C35—C36—H36B	109.5
C18'—C17—H17C	106.6	H36A—C36—H36B	109.5
C16—C17—H17C	106.6	C35—C36—H36C	109.5
H17A—C17—H17C	114.1	H36A—C36—H36C	109.5
H17B—C17—H17C	109.0	H36B—C36—H36C	109.5
C18—C17—H17D	102.2
S8—Zn1—S1—C1	107.04 (15)	S4—Zn2—S5—C19	105.01 (17)
S3—Zn1—S1—C1	−100.94 (15)	S7—Zn2—S5—C19	−101.14 (17)
S2—Zn1—S1—C1	1.40 (15)	S6—Zn2—S5—C19	0.23 (17)
S8—Zn1—S2—C1	−124.51 (15)	S4—Zn2—S6—C19	−120.83 (17)
S1—Zn1—S2—C1	−1.42 (15)	S5—Zn2—S6—C19	−0.23 (17)
S3—Zn1—S2—C1	112.45 (15)	S7—Zn2—S6—C19	116.76 (17)
C6—N1—C1—S2	1.8 (6)	C20—N3—C19—S6	−176.8 (4)
C2—N1—C1—S2	−177.9 (3)	C24—N3—C19—S6	5.5 (7)
C6—N1—C1—S1	−176.9 (3)	C20—N3—C19—S5	5.4 (7)
C2—N1—C1—S1	3.3 (6)	C24—N3—C19—S5	−172.3 (4)
Zn1—S2—C1—N1	−176.7 (4)	Zn2—S6—C19—N3	−177.6 (4)
Zn1—S2—C1—S1	2.1 (2)	Zn2—S6—C19—S5	0.3 (3)
Zn1—S1—C1—N1	176.6 (4)	Zn2—S5—C19—N3	177.6 (4)
Zn1—S1—C1—S2	−2.2 (2)	Zn2—S5—C19—S6	−0.4 (3)
C1—N1—C2—C3	88.3 (6)	C19—N3—C20—C21	85.7 (7)
C6—N1—C2—C3	−91.5 (5)	C24—N3—C20—C21	−96.5 (6)
N1—C2—C3—C4	−173.2 (4)	N3—C20—C21—C22	179.7 (5)
C2—C3—C4—C5	−179.7 (5)	C20—C21—C22—C23	−178.8 (5)
C1—N1—C6—C7	−84.1 (6)	C19—N3—C24—C25	−85.4 (8)
C2—N1—C6—C7	95.6 (6)	C20—N3—C24—C25	96.8 (7)
N1—C6—C7—C8	179.3 (6)	N3—C24—C25—C26	164.0 (7)
C6—C7—C8—C9	−172.1 (9)	C24—C25—C26—C27	66.4 (11)
S8—Zn1—S3—C10	−19.22 (17)	S4—Zn2—S7—C28	−19.10 (16)
S1—Zn1—S3—C10	−174.79 (16)	S5—Zn2—S7—C28	−175.52 (15)
S2—Zn1—S3—C10	102.62 (16)	S6—Zn2—S7—C28	101.49 (16)
S5—Zn2—S4—C10	74.81 (15)	S1—Zn1—S8—C28	73.04 (14)
S7—Zn2—S4—C10	−80.60 (15)	S3—Zn1—S8—C28	−79.91 (13)
S6—Zn2—S4—C10	160.70 (14)	S2—Zn1—S8—C28	160.33 (13)
C11—N2—C10—S4	177.7 (3)	C33—N4—C28—S8	−1.5 (5)
C15—N2—C10—S4	0.4 (5)	C29—N4—C28—S8	177.2 (3)
C11—N2—C10—S3	0.1 (6)	C33—N4—C28—S7	−178.9 (3)
C15—N2—C10—S3	−177.1 (3)	C29—N4—C28—S7	−0.2 (5)
Zn2—S4—C10—N2	−178.5 (3)	Zn1—S8—C28—N4	−179.5 (3)
Zn2—S4—C10—S3	−0.9 (2)	Zn1—S8—C28—S7	−2.0 (2)
Zn1—S3—C10—N2	−96.2 (3)	Zn2—S7—C28—N4	−95.3 (3)
Zn1—S3—C10—S4	86.3 (2)	Zn2—S7—C28—S8	87.2 (2)
C10—N2—C11—C12	104.8 (5)	C28—N4—C29—C30	106.6 (5)
C15—N2—C11—C12	−77.8 (6)	C33—N4—C29—C30	−74.6 (5)
N2—C11—C12—C13	−180.0 (5)	N4—C29—C30—C31	−178.1 (4)
C11—C12—C13—C14	−179.9 (5)	C29—C30—C31—C32	179.3 (5)
C10—N2—C15—C16	−86.2 (6)	C28—N4—C33—C34	−81.8 (5)
C11—N2—C15—C16	96.3 (5)	C29—N4—C33—C34	99.4 (5)
N2—C15—C16—C17	−175.8 (6)	N4—C33—C34—C35	179.3 (6)
C15—C16—C17—C18	−65.5 (14)	C33—C34—C35—C36	173.2 (9)
C15—C16—C17—C18'	168.2 (19)