Chloro­(diethyl­amino)­tris(μ-diethyl­carbamato)­dizinc(II): an example of the generality of the threefold paddlewheel structure in carbamatozinc chemistry

McCowan, C.S.; Buss, C.E.; Young Jr, V.G.; McDonnell, R.L.; Caudle, M.T.

doi:10.1107/S1600536804002193

Chloro(diethylamino)tris(μ-diethylcarbamato)dizinc(II): an example of the generality of the threefold paddlewheel structure in carbamatozinc chemistry

C. S. McCowan, C. E. Buss, V. G. Young Jr, R. L. McDonnell and M. T. Caudle

The title complex, [Zn₂(C₅H₁₀NO₂)₃Cl(C₄H₁₁N)] or [Zn₂{O₂CN(C₂H₅)₂}₃Cl{HN(C₂H₅)₂}], consists of a dinuclear Zn₂(O₂CNEt₂)₃⁺ core bridged by three diethylcarbamate ligands in a μ_1,3 manner and capped by chloride and diethylamine ligands. This threefold paddlewheel structure is common in carbamatozinc coordination chemistry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002193/om6209sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002193/om6209Isup2.hkl Contains datablock I

CCDC reference: 236025

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.023
wR factor = 0.056
Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT301_ALERT_3_B Main Residue  Disorder .........................      33.00 Perc.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

[Zn₂(C₅H₁₀NO₂)₃Cl(C₄H₁₁N)]	D_x = 1.436 Mg m⁻³
M_r = 587.75	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5348 reflections
a = 16.3204 (12) Å	θ = 2.2–24.9°
b = 17.8489 (13) Å	µ = 1.90 mm⁻¹
c = 18.6636 (14) Å	T = 173 K
V = 5436.7 (7) Å³	Irregular Block, colorless
Z = 8	0.35 × 0.35 × 0.20 mm
F(000) = 2464

Data collection top

Bruker CCD diffractometer	4807 independent reflections
Radiation source: normal-focus sealed tube	3841 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω and φ scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −19→19
T_min = 0.539, T_max = 0.681	k = −21→14
27209 measured reflections	l = −20→22

Refinement top

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0294P)² + 0.4305P] where P = (F_o² + 2F_c²)/3
4807 reflections	(Δ/σ)_max = 0.002
381 parameters	Δρ_max = 0.23 e Å⁻³
192 restraints	Δρ_min = −0.38 e Å⁻³

Special details top

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.

Non-bonded distance for Zn1···ZN2 is 3.2975 (4) angstrom.

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.

A direct methods solution was calculated that provides most of the non-hydrogen atoms. Several full-matrix least squares/difference Fourier cycles located the remainder of the non-hydrogen atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.182355 (14)	0.105343 (12)	0.740612 (12)	0.02712 (7)
Zn2	0.156906 (13)	0.285547 (13)	0.772550 (12)	0.02813 (7)
Cl1	0.12096 (3)	0.40574 (3)	0.77789 (3)	0.03839 (13)
O10	0.1828 (3)	0.2678 (3)	0.6717 (3)	0.0358 (9)	0.727 (5)
O11	0.1907 (12)	0.1456 (3)	0.6454 (4)	0.0379 (14)	0.727 (5)
C10	0.1883 (5)	0.2139 (3)	0.6277 (3)	0.0272 (14)	0.727 (5)
N10	0.1947 (3)	0.2300 (2)	0.5571 (2)	0.0350 (11)	0.727 (5)
C11	0.2026 (3)	0.3072 (2)	0.5323 (2)	0.0607 (13)	0.727 (5)
H11A	0.2531	0.3114	0.5031	0.073*	0.727 (5)
H11B	0.2092	0.3402	0.5745	0.073*	0.727 (5)
C12	0.1317 (2)	0.3351 (2)	0.4886 (2)	0.0693 (14)	0.727 (5)
H12A	0.1405	0.3879	0.4764	0.104*	0.727 (5)
H12B	0.0811	0.3300	0.5164	0.104*	0.727 (5)
H12C	0.1274	0.3055	0.4445	0.104*	0.727 (5)
C13	0.1978 (6)	0.1694 (4)	0.5038 (4)	0.0472 (13)	0.727 (5)
H13A	0.2317	0.1280	0.5229	0.057*	0.727 (5)
H13B	0.2249	0.1884	0.4599	0.057*	0.727 (5)
C14	0.1140 (8)	0.1390 (4)	0.4840 (7)	0.0548 (16)	0.727 (5)
H14A	0.1198	0.1013	0.4461	0.082*	0.727 (5)
H14B	0.0792	0.1800	0.4669	0.082*	0.727 (5)
H14C	0.0888	0.1159	0.5263	0.082*	0.727 (5)
O10'	0.1612 (8)	0.2563 (9)	0.6718 (8)	0.0358 (9)	0.273 (5)
O11'	0.184 (3)	0.1371 (8)	0.6388 (12)	0.0379 (14)	0.273 (5)
C10'	0.1739 (18)	0.2062 (8)	0.6250 (7)	0.0272 (14)	0.273 (5)
N10'	0.1720 (9)	0.2259 (5)	0.5551 (7)	0.0350 (11)	0.273 (5)
C11'	0.1454 (6)	0.3006 (5)	0.5323 (5)	0.049 (3)	0.273 (5)
H11C	0.1195	0.3262	0.5735	0.058*	0.273 (5)
H11D	0.1033	0.2949	0.4945	0.058*	0.273 (5)
C12'	0.2132 (6)	0.3491 (5)	0.5041 (6)	0.056 (3)	0.273 (5)
H12D	0.1918	0.3994	0.4942	0.084*	0.273 (5)
H12E	0.2350	0.3273	0.4599	0.084*	0.273 (5)
H12F	0.2570	0.3525	0.5399	0.084*	0.273 (5)
C13'	0.1863 (18)	0.1692 (10)	0.4995 (11)	0.0472 (13)	0.273 (5)
H13C	0.2331	0.1374	0.5139	0.057*	0.273 (5)
H13D	0.2013	0.1948	0.4542	0.057*	0.273 (5)
C14'	0.113 (2)	0.1200 (13)	0.486 (2)	0.0548 (16)	0.273 (5)
H14D	0.1268	0.0812	0.4511	0.082*	0.273 (5)
H14E	0.0675	0.1505	0.4676	0.082*	0.273 (5)
H14F	0.0959	0.0962	0.5312	0.082*	0.273 (5)
O20	0.0732 (2)	0.2264 (2)	0.82537 (19)	0.0354 (8)	0.718 (5)
O21	0.0711 (4)	0.1117 (3)	0.7740 (3)	0.0335 (12)	0.718 (5)
C20	0.0410 (3)	0.1626 (3)	0.8141 (5)	0.0295 (14)	0.718 (5)
N20	−0.02969 (19)	0.14722 (16)	0.84851 (17)	0.0316 (8)	0.718 (5)
C21	−0.06730 (18)	0.20322 (18)	0.89520 (16)	0.0367 (9)	0.718 (5)
H21A	−0.0243	0.2256	0.9259	0.044*	0.718 (5)
H21B	−0.1074	0.1780	0.9269	0.044*	0.718 (5)
C22	−0.1100 (2)	0.2647 (2)	0.8550 (3)	0.0606 (13)	0.718 (5)
H22A	−0.1392	0.2971	0.8889	0.091*	0.718 (5)
H22B	−0.1492	0.2429	0.8212	0.091*	0.718 (5)
H22C	−0.0695	0.2945	0.8287	0.091*	0.718 (5)
C23	−0.0718 (5)	0.0755 (3)	0.8396 (4)	0.0390 (10)	0.718 (5)
H23A	−0.0513	0.0508	0.7956	0.047*	0.718 (5)
H23B	−0.1311	0.0849	0.8331	0.047*	0.718 (5)
C24	−0.0600 (7)	0.0230 (3)	0.9025 (5)	0.0647 (15)	0.718 (5)
H24A	−0.0889	−0.0242	0.8932	0.097*	0.718 (5)
H24B	−0.0820	0.0462	0.9460	0.097*	0.718 (5)
H24C	−0.0015	0.0129	0.9089	0.097*	0.718 (5)
O20'	0.0594 (6)	0.2344 (5)	0.7946 (5)	0.035 (2)	0.282 (5)
O21'	0.0774 (10)	0.1102 (9)	0.7894 (11)	0.0335 (12)	0.282 (5)
C20'	0.0337 (7)	0.1678 (6)	0.8021 (15)	0.0295 (14)	0.282 (5)
N20'	−0.0454 (5)	0.1578 (4)	0.8205 (5)	0.0316 (8)	0.282 (5)
C21'	−0.0997 (4)	0.2220 (5)	0.8336 (4)	0.035 (2)	0.282 (5)
H21C	−0.1570	0.2067	0.8241	0.042*	0.282 (5)
H21D	−0.0857	0.2627	0.7997	0.042*	0.282 (5)
C22'	−0.0936 (6)	0.2514 (7)	0.9088 (5)	0.062 (3)	0.282 (5)
H22D	−0.1308	0.2940	0.9146	0.093*	0.282 (5)
H22E	−0.0372	0.2675	0.9182	0.093*	0.282 (5)
H22F	−0.1087	0.2118	0.9426	0.093*	0.282 (5)
C23'	−0.0792 (13)	0.0828 (7)	0.8319 (12)	0.0390 (10)	0.282 (5)
H23C	−0.0575	0.0493	0.7942	0.047*	0.282 (5)
H23D	−0.1394	0.0854	0.8256	0.047*	0.282 (5)
C24'	−0.061 (2)	0.0481 (9)	0.9038 (13)	0.0647 (15)	0.282 (5)
H24D	−0.0882	0.0775	0.9415	0.097*	0.282 (5)
H24E	−0.0022	0.0475	0.9121	0.097*	0.282 (5)
H24F	−0.0825	−0.0033	0.9047	0.097*	0.282 (5)
O30	0.25895 (8)	0.26442 (7)	0.82331 (7)	0.0340 (3)
O31	0.27042 (8)	0.14075 (8)	0.80043 (8)	0.0388 (4)
C30	0.29663 (12)	0.20194 (12)	0.82663 (10)	0.0305 (5)
N30	0.36934 (10)	0.19957 (9)	0.86092 (9)	0.0356 (4)
C31	0.40371 (13)	0.26630 (13)	0.89533 (12)	0.0449 (6)
H31A	0.4266	0.2521	0.9425	0.054*
H31B	0.3593	0.3030	0.9037	0.054*
C32	0.47013 (15)	0.30273 (15)	0.85092 (17)	0.0708 (9)
H32A	0.4885	0.3488	0.8746	0.106*
H32B	0.4485	0.3149	0.8033	0.106*
H32C	0.5165	0.2682	0.8461	0.106*
C33	0.41691 (14)	0.13013 (13)	0.86532 (12)	0.0454 (6)
H33A	0.4760	0.1424	0.8629	0.054*
H33B	0.4036	0.0982	0.8235	0.054*
C34	0.40035 (15)	0.08656 (14)	0.93319 (14)	0.0593 (7)
H34A	0.4343	0.0413	0.9338	0.089*
H34B	0.3424	0.0724	0.9349	0.089*
H34C	0.4136	0.1177	0.9748	0.089*
N40	0.20388 (10)	−0.00661 (9)	0.73661 (8)	0.0310 (4)
H40	0.2594	−0.0129	0.7459	0.037*
C41	0.18895 (14)	−0.03886 (13)	0.66441 (12)	0.0445 (6)
H41A	0.2026	−0.0929	0.6652	0.053*
H41B	0.2258	−0.0142	0.6294	0.053*
C42	0.10141 (15)	−0.02940 (14)	0.64009 (13)	0.0563 (7)
H42A	0.0959	−0.0473	0.5907	0.084*
H42B	0.0863	0.0237	0.6423	0.084*
H42C	0.0651	−0.0584	0.6714	0.084*
C43	0.15920 (13)	−0.04960 (12)	0.79335 (12)	0.0398 (5)
H43A	0.1704	−0.1038	0.7875	0.048*
H43B	0.0995	−0.0417	0.7878	0.048*
C44	0.18541 (15)	−0.02490 (13)	0.86726 (12)	0.0515 (6)
H44A	0.1552	−0.0536	0.9034	0.077*
H44C	0.1737	0.0286	0.8732	0.077*
H44D	0.2443	−0.0337	0.8731	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03085 (13)	0.02458 (13)	0.02592 (13)	0.00225 (10)	0.00163 (10)	−0.00009 (9)
Zn2	0.02410 (13)	0.02514 (13)	0.03513 (14)	−0.00051 (10)	0.00178 (10)	−0.00180 (10)
Cl1	0.0355 (3)	0.0259 (3)	0.0537 (3)	0.0017 (2)	0.0016 (2)	0.0002 (2)
O10	0.040 (3)	0.037 (2)	0.0314 (9)	−0.0017 (16)	−0.0030 (16)	−0.0046 (11)
O11	0.060 (3)	0.0301 (15)	0.0241 (18)	−0.005 (3)	−0.002 (2)	−0.0003 (14)
C10	0.015 (4)	0.0377 (17)	0.0284 (12)	−0.0041 (18)	−0.0012 (12)	−0.0005 (11)
N10	0.042 (3)	0.0377 (12)	0.0257 (10)	−0.0058 (14)	−0.0001 (16)	0.0066 (8)
C11	0.083 (3)	0.057 (3)	0.043 (2)	−0.025 (3)	−0.021 (2)	0.017 (2)
C12	0.084 (3)	0.068 (3)	0.056 (3)	0.011 (2)	−0.002 (2)	0.021 (2)
C13	0.056 (3)	0.0600 (17)	0.0256 (15)	0.0058 (16)	0.0081 (17)	0.0007 (11)
C14	0.080 (2)	0.043 (4)	0.0417 (17)	−0.006 (4)	−0.0008 (16)	−0.006 (4)
O10'	0.040 (3)	0.037 (2)	0.0314 (9)	−0.0017 (16)	−0.0030 (16)	−0.0046 (11)
O11'	0.060 (3)	0.0301 (15)	0.0241 (18)	−0.005 (3)	−0.002 (2)	−0.0003 (14)
C10'	0.015 (4)	0.0377 (17)	0.0284 (12)	−0.0041 (18)	−0.0012 (12)	−0.0005 (11)
N10'	0.042 (3)	0.0377 (12)	0.0257 (10)	−0.0058 (14)	−0.0001 (16)	0.0066 (8)
C11'	0.047 (6)	0.065 (8)	0.034 (6)	0.015 (6)	−0.004 (5)	0.010 (5)
C12'	0.069 (7)	0.048 (7)	0.051 (6)	−0.002 (5)	0.008 (5)	0.011 (5)
C13'	0.056 (3)	0.0600 (17)	0.0256 (15)	0.0058 (16)	0.0081 (17)	0.0007 (11)
C14'	0.080 (2)	0.043 (4)	0.0417 (17)	−0.006 (4)	−0.0008 (16)	−0.006 (4)
O20	0.0373 (17)	0.0290 (16)	0.040 (2)	−0.0086 (13)	0.0141 (15)	−0.0022 (16)
O21	0.0294 (13)	0.0299 (9)	0.041 (3)	0.0024 (8)	0.0045 (17)	−0.0076 (15)
C20	0.0293 (14)	0.0273 (14)	0.032 (4)	−0.0007 (11)	0.0023 (18)	0.0016 (14)
N20	0.0304 (15)	0.0266 (13)	0.038 (2)	−0.0037 (11)	0.0115 (15)	−0.0008 (14)
C21	0.0319 (18)	0.038 (2)	0.040 (2)	−0.0051 (15)	0.0116 (14)	−0.0056 (15)
C22	0.055 (3)	0.057 (3)	0.070 (4)	0.016 (2)	0.016 (2)	−0.004 (2)
C23	0.0331 (19)	0.0331 (16)	0.051 (2)	−0.0090 (15)	0.0047 (15)	0.0004 (15)
C24	0.080 (2)	0.042 (4)	0.071 (2)	−0.005 (4)	0.0101 (17)	0.016 (3)
O20'	0.035 (4)	0.022 (4)	0.047 (6)	−0.003 (3)	0.015 (4)	0.005 (4)
O21'	0.0294 (13)	0.0299 (9)	0.041 (3)	0.0024 (8)	0.0045 (17)	−0.0076 (15)
C20'	0.0293 (14)	0.0273 (14)	0.032 (4)	−0.0007 (11)	0.0023 (18)	0.0016 (14)
N20'	0.0304 (15)	0.0266 (13)	0.038 (2)	−0.0037 (11)	0.0115 (15)	−0.0008 (14)
C21'	0.023 (4)	0.053 (6)	0.028 (5)	−0.006 (4)	−0.001 (3)	0.002 (4)
C22'	0.063 (7)	0.075 (9)	0.048 (7)	0.007 (6)	−0.010 (5)	−0.017 (6)
C23'	0.0331 (19)	0.0331 (16)	0.051 (2)	−0.0090 (15)	0.0047 (15)	0.0004 (15)
C24'	0.080 (2)	0.042 (4)	0.071 (2)	−0.005 (4)	0.0101 (17)	0.016 (3)
O30	0.0339 (8)	0.0294 (8)	0.0387 (8)	0.0026 (6)	−0.0060 (6)	0.0012 (6)
O31	0.0408 (9)	0.0314 (9)	0.0442 (9)	0.0030 (7)	−0.0132 (7)	−0.0036 (7)
C30	0.0314 (11)	0.0370 (13)	0.0231 (11)	0.0000 (10)	0.0028 (9)	0.0032 (9)
N30	0.0287 (9)	0.0402 (11)	0.0379 (10)	0.0035 (8)	−0.0068 (8)	−0.0028 (8)
C31	0.0410 (13)	0.0518 (16)	0.0420 (14)	0.0020 (11)	−0.0112 (11)	−0.0019 (11)
C32	0.0403 (15)	0.066 (2)	0.106 (3)	−0.0053 (13)	0.0019 (15)	0.0105 (17)
C33	0.0401 (13)	0.0514 (15)	0.0447 (14)	0.0150 (12)	−0.0080 (11)	−0.0028 (11)
C34	0.0580 (17)	0.0525 (17)	0.0673 (18)	0.0059 (13)	−0.0086 (14)	0.0121 (13)
N40	0.0327 (9)	0.0280 (10)	0.0322 (10)	0.0046 (8)	0.0010 (7)	−0.0032 (7)
C41	0.0545 (14)	0.0364 (14)	0.0424 (14)	0.0072 (11)	0.0015 (11)	−0.0131 (10)
C42	0.0695 (17)	0.0510 (17)	0.0485 (16)	−0.0004 (13)	−0.0168 (13)	−0.0135 (12)
C43	0.0453 (13)	0.0271 (12)	0.0471 (14)	0.0030 (10)	0.0053 (11)	0.0046 (10)
C44	0.0695 (17)	0.0465 (15)	0.0384 (14)	0.0073 (13)	0.0076 (12)	0.0105 (11)

Geometric parameters (Å, º) top

Zn1—Zn2	3.2975 (4)	C22—H22C	0.9800
Zn1—O11	1.922 (8)	C23—C24	1.514 (4)
Zn1—O21	1.923 (6)	C23—H23A	0.9900
Zn1—O31	1.9265 (14)	C23—H23B	0.9900
Zn1—O21'	1.942 (16)	C24—H24A	0.9800
Zn1—O11'	1.98 (2)	C24—H24B	0.9800
Zn1—N40	2.0302 (16)	C24—H24C	0.9800
Zn2—O20'	1.881 (9)	O20'—C20'	1.269 (6)
Zn2—O10'	1.953 (14)	O21'—C20'	1.272 (7)
Zn2—O30	1.9527 (13)	C20'—N20'	1.347 (7)
Zn2—O10	1.955 (5)	N20'—C23'	1.463 (6)
Zn2—O20	1.988 (4)	N20'—C21'	1.469 (6)
Zn2—Cl1	2.2262 (6)	C21'—C22'	1.502 (7)
O10—C10	1.268 (3)	C21'—H21C	0.9900
O11—C10	1.265 (4)	C21'—H21D	0.9900
C10—N10	1.352 (3)	C22'—H22D	0.9800
N10—C11	1.459 (4)	C22'—H22E	0.9800
N10—C13	1.470 (4)	C22'—H22F	0.9800
C11—C12	1.500 (5)	C23'—C24'	1.508 (7)
C11—H11A	0.9900	C23'—H23C	0.9900
C11—H11B	0.9900	C23'—H23D	0.9900
C12—H12A	0.9800	C24'—H24D	0.9800
C12—H12B	0.9800	C24'—H24E	0.9800
C12—H12C	0.9800	C24'—H24F	0.9800
C13—C14	1.517 (5)	O30—C30	1.275 (2)
C13—H13A	0.9900	O31—C30	1.271 (2)
C13—H13B	0.9900	C30—N30	1.349 (2)
C14—H14A	0.9800	N30—C33	1.465 (3)
C14—H14B	0.9800	N30—C31	1.465 (3)
C14—H14C	0.9800	C31—C32	1.512 (3)
O10'—C10'	1.268 (7)	C31—H31A	0.9900
O11'—C10'	1.270 (7)	C31—H31B	0.9900
C10'—N10'	1.352 (7)	C32—H32A	0.9800
N10'—C11'	1.464 (7)	C32—H32B	0.9800
N10'—C13'	1.469 (7)	C32—H32C	0.9800
C11'—C12'	1.500 (7)	C33—C34	1.511 (3)
C11'—H11C	0.9900	C33—H33A	0.9900
C11'—H11D	0.9900	C33—H33B	0.9900
C12'—H12D	0.9800	C34—H34A	0.9800
C12'—H12E	0.9800	C34—H34B	0.9800
C12'—H12F	0.9800	C34—H34C	0.9800
C13'—C14'	1.510 (7)	N40—C41	1.486 (3)
C13'—H13C	0.9900	N40—C43	1.497 (3)
C13'—H13D	0.9900	N40—H40	0.9300
C14'—H14D	0.9800	C41—C42	1.509 (3)
C14'—H14E	0.9800	C41—H41A	0.9900
C14'—H14F	0.9800	C41—H41B	0.9900
O20—C20	1.273 (4)	C42—H42A	0.9800
O21—C20	1.275 (5)	C42—H42B	0.9800
C20—N20	1.349 (4)	C42—H42C	0.9800
N20—C21	1.461 (4)	C43—C44	1.510 (3)
N20—C23	1.463 (4)	C43—H43A	0.9900
C21—C22	1.502 (4)	C43—H43B	0.9900
C21—H21A	0.9900	C44—H44A	0.9800
C21—H21B	0.9900	C44—H44C	0.9800
C22—H22A	0.9800	C44—H44D	0.9800
C22—H22B	0.9800

Zn1···Zn2	3.2975 (4)	Zn2···O21	3.405 (6)
Zn1···O30	3.4651 (13)	Zn2···O21'	3.403 (16)
Zn1···O20	3.216 (3)	Zn2···O11	3.489 (7)
Zn1···O20'	3.217 (9)	Zn2···O11'	3.667 (19)
Zn1···O10	3.172 (5)	Zn2···O31	3.2222 (14)
Zn1···O10'	3.005 (16)

O11—Zn1—O21	110.2 (6)	C22—C21—H21A	108.9
O11—Zn1—O31	111.1 (5)	N20—C21—H21B	108.9
O21—Zn1—O31	119.83 (19)	C22—C21—H21B	108.9
O11—Zn1—O21'	118.7 (8)	H21A—C21—H21B	107.7
O21—Zn1—O21'	9.1 (8)	N20—C23—C24	113.2 (4)
O31—Zn1—O21'	111.8 (6)	N20—C23—H23A	108.9
O11—Zn1—O11'	6.3 (14)	C24—C23—H23A	108.9
O21—Zn1—O11'	107.9 (16)	N20—C23—H23B	108.9
O31—Zn1—O11'	116.8 (14)	C24—C23—H23B	108.9
O21'—Zn1—O11'	116.7 (17)	H23A—C23—H23B	107.8
O11—Zn1—N40	108.7 (2)	C20'—O20'—Zn2	139.4 (8)
O21—Zn1—N40	103.48 (19)	C20'—O21'—Zn1	128.2 (13)
O31—Zn1—N40	102.42 (6)	O20'—C20'—O21'	123.4 (10)
O21'—Zn1—N40	102.4 (5)	O20'—C20'—N20'	117.9 (8)
O11'—Zn1—N40	104.1 (6)	O21'—C20'—N20'	118.6 (10)
O20'—Zn2—O10'	96.4 (5)	C20'—N20'—C23'	121.3 (9)
O20'—Zn2—O30	121.5 (3)	C20'—N20'—C21'	121.2 (6)
O10'—Zn2—O30	112.7 (5)	C23'—N20'—C21'	117.4 (9)
O20'—Zn2—O10	108.3 (3)	N20'—C21'—C22'	112.8 (7)
O10'—Zn2—O10	12.0 (4)	N20'—C21'—H21C	109.0
O30—Zn2—O10	104.57 (15)	C22'—C21'—H21C	109.0
O20'—Zn2—O20	18.6 (2)	N20'—C21'—H21D	109.0
O10'—Zn2—O20	111.1 (4)	C22'—C21'—H21D	109.0
O30—Zn2—O20	104.07 (12)	H21C—C21'—H21D	107.8
O10—Zn2—O20	122.70 (16)	N20'—C23'—C24'	115.6 (10)
O20'—Zn2—Cl1	103.6 (3)	N20'—C23'—H23C	108.4
O10'—Zn2—Cl1	108.0 (5)	C24'—C23'—H23C	108.4
O30—Zn2—Cl1	112.89 (4)	N20'—C23'—H23D	108.4
O10—Zn2—Cl1	104.83 (17)	C24'—C23'—H23D	108.4
O20—Zn2—Cl1	107.94 (13)	H23C—C23'—H23D	107.4
C10—O10—Zn2	139.6 (4)	C30—O30—Zn2	127.14 (13)
C10—O11—Zn1	126.8 (5)	C30—O31—Zn1	139.11 (13)
O11—C10—O10	124.4 (4)	O31—C30—O30	124.80 (18)
O11—C10—N10	117.2 (4)	O31—C30—N30	116.85 (18)
O10—C10—N10	118.4 (4)	O30—C30—N30	118.34 (18)
C10—N10—C11	121.1 (3)	C30—N30—C33	121.29 (18)
C10—N10—C13	120.4 (4)	C30—N30—C31	121.29 (17)
C11—N10—C13	118.4 (4)	C33—N30—C31	117.42 (17)
N10—C11—C12	114.7 (4)	N30—C31—C32	112.6 (2)
N10—C11—H11A	108.6	N30—C31—H31A	109.1
C12—C11—H11A	108.6	C32—C31—H31A	109.1
N10—C11—H11B	108.6	N30—C31—H31B	109.1
C12—C11—H11B	108.6	C32—C31—H31B	109.1
H11A—C11—H11B	107.6	H31A—C31—H31B	107.8
N10—C13—C14	113.4 (4)	C31—C32—H32A	109.5
N10—C13—H13A	108.9	C31—C32—H32B	109.5
C14—C13—H13A	108.9	H32A—C32—H32B	109.5
N10—C13—H13B	108.9	C31—C32—H32C	109.5
C14—C13—H13B	108.9	H32A—C32—H32C	109.5
H13A—C13—H13B	107.7	H32B—C32—H32C	109.5
C10'—O10'—Zn2	149.1 (12)	N30—C33—C34	112.82 (19)
C10'—O11'—Zn1	118.0 (14)	N30—C33—H33A	109.0
O10'—C10'—O11'	124.6 (11)	C34—C33—H33A	109.0
O10'—C10'—N10'	118.5 (9)	N30—C33—H33B	109.0
O11'—C10'—N10'	116.9 (10)	C34—C33—H33B	109.0
C10'—N10'—C11'	121.7 (8)	H33A—C33—H33B	107.8
C10'—N10'—C13'	119.9 (9)	C33—C34—H34A	109.5
C11'—N10'—C13'	117.9 (9)	C33—C34—H34B	109.5
N10'—C11'—C12'	114.1 (8)	H34A—C34—H34B	109.5
N10'—C11'—H11C	108.7	C33—C34—H34C	109.5
C12'—C11'—H11C	108.7	H34A—C34—H34C	109.5
N10'—C11'—H11D	108.7	H34B—C34—H34C	109.5
C12'—C11'—H11D	108.7	C41—N40—C43	111.29 (17)
H11C—C11'—H11D	107.6	C41—N40—Zn1	112.73 (13)
C11'—C12'—H12D	109.5	C43—N40—Zn1	113.21 (12)
C11'—C12'—H12E	109.5	C41—N40—H40	106.3
H12D—C12'—H12E	109.5	C43—N40—H40	106.3
C11'—C12'—H12F	109.5	Zn1—N40—H40	106.3
H12D—C12'—H12F	109.5	N40—C41—C42	112.63 (18)
H12E—C12'—H12F	109.5	N40—C41—H41A	109.1
N10'—C13'—C14'	113.1 (11)	C42—C41—H41A	109.1
N10'—C13'—H13C	109.0	N40—C41—H41B	109.1
C14'—C13'—H13C	109.0	C42—C41—H41B	109.1
N10'—C13'—H13D	109.0	H41A—C41—H41B	107.8
C14'—C13'—H13D	109.0	C41—C42—H42A	109.5
H13C—C13'—H13D	107.8	C41—C42—H42B	109.5
C13'—C14'—H14D	109.5	H42A—C42—H42B	109.5
C13'—C14'—H14E	109.5	C41—C42—H42C	109.5
H14D—C14'—H14E	109.5	H42A—C42—H42C	109.5
C13'—C14'—H14F	109.5	H42B—C42—H42C	109.5
H14D—C14'—H14F	109.5	N40—C43—C44	111.01 (18)
H14E—C14'—H14F	109.5	N40—C43—H43A	109.4
C20—O20—Zn2	132.6 (4)	C44—C43—H43A	109.4
C20—O21—Zn1	126.5 (5)	N40—C43—H43B	109.4
O20—C20—O21	125.2 (4)	C44—C43—H43B	109.4
O20—C20—N20	117.1 (4)	H43A—C43—H43B	108.0
O21—C20—N20	117.6 (4)	C43—C44—H44A	109.5
C20—N20—C21	120.3 (3)	C43—C44—H44C	109.5
C20—N20—C23	121.7 (4)	H44A—C44—H44C	109.5
C21—N20—C23	118.0 (4)	C43—C44—H44D	109.5
N20—C21—C22	113.4 (3)	H44A—C44—H44D	109.5
N20—C21—H21A	108.9	H44C—C44—H44D	109.5

O20'—Zn2—O10—C10	−48.6 (8)	C20—N20—C21—C22	76.1 (6)
O10'—Zn2—O10—C10	−52 (3)	C23—N20—C21—C22	−102.7 (5)
O30—Zn2—O10—C10	82.3 (7)	C20—N20—C23—C24	103.3 (8)
O20—Zn2—O10—C10	−35.5 (8)	C21—N20—C23—C24	−77.9 (8)
Cl1—Zn2—O10—C10	−158.8 (7)	O10'—Zn2—O20'—C20'	71 (2)
O21—Zn1—O11—C10	73.9 (16)	O30—Zn2—O20'—C20'	−51 (2)
O31—Zn1—O11—C10	−61.3 (17)	O10—Zn2—O20'—C20'	70 (2)
O21'—Zn1—O11—C10	70.4 (18)	O20—Zn2—O20'—C20'	−73 (2)
O11'—Zn1—O11—C10	144 (18)	Cl1—Zn2—O20'—C20'	−179 (2)
N40—Zn1—O11—C10	−173.3 (14)	O11—Zn1—O21'—C20'	−56 (2)
Zn1—O11—C10—O10	3 (2)	O21—Zn1—O21'—C20'	−78 (4)
Zn1—O11—C10—N10	−179.5 (10)	O31—Zn1—O21'—C20'	75 (2)
Zn2—O10—C10—O11	−13.9 (17)	O11'—Zn1—O21'—C20'	−63 (2)
Zn2—O10—C10—N10	168.3 (4)	N40—Zn1—O21'—C20'	−176 (2)
O11—C10—N10—C11	−172.5 (11)	Zn2—O20'—C20'—O21'	−5 (4)
O10—C10—N10—C11	5.5 (10)	Zn2—O20'—C20'—N20'	178.6 (9)
O11—C10—N10—C13	4.6 (14)	Zn1—O21'—C20'—O20'	−12 (4)
O10—C10—N10—C13	−177.4 (7)	Zn1—O21'—C20'—N20'	163.8 (16)
C10—N10—C11—C12	−114.6 (6)	O20'—C20'—N20'—C23'	−178.6 (17)
C13—N10—C11—C12	68.2 (7)	O21'—C20'—N20'—C23'	5 (3)
C10—N10—C13—C14	82.0 (9)	O20'—C20'—N20'—C21'	−2 (3)
C11—N10—C13—C14	−100.8 (7)	O21'—C20'—N20'—C21'	−178.0 (18)
O20'—Zn2—O10'—C10'	−73 (3)	C20'—N20'—C21'—C22'	−84.7 (17)
O30—Zn2—O10'—C10'	55 (3)	C23'—N20'—C21'—C22'	92.2 (13)
O10—Zn2—O10'—C10'	104 (5)	C20'—N20'—C23'—C24'	80 (3)
O20—Zn2—O10'—C10'	−61 (3)	C21'—N20'—C23'—C24'	−96 (2)
Cl1—Zn2—O10'—C10'	−180 (3)	O20'—Zn2—O30—C30	59.8 (4)
O11—Zn1—O11'—C10'	−40 (14)	O10'—Zn2—O30—C30	−53.6 (5)
O21—Zn1—O11'—C10'	72 (4)	O10—Zn2—O30—C30	−62.9 (2)
O31—Zn1—O11'—C10'	−66 (4)	O20—Zn2—O30—C30	66.9 (2)
O21'—Zn1—O11'—C10'	70 (4)	Cl1—Zn2—O30—C30	−176.33 (14)
N40—Zn1—O11'—C10'	−179 (4)	O11—Zn1—O31—C30	64.6 (4)
Zn2—O10'—C10'—O11'	9 (6)	O21—Zn1—O31—C30	−65.7 (3)
Zn2—O10'—C10'—N10'	−174.7 (15)	O21'—Zn1—O31—C30	−70.5 (6)
Zn1—O11'—C10'—O10'	−1 (6)	O11'—Zn1—O31—C30	67.6 (10)
Zn1—O11'—C10'—N10'	−177 (2)	N40—Zn1—O31—C30	−179.4 (2)
O10'—C10'—N10'—C11'	−8 (3)	Zn1—O31—C30—O30	7.8 (3)
O11'—C10'—N10'—C11'	168 (3)	Zn1—O31—C30—N30	−172.88 (14)
O10'—C10'—N10'—C13'	−180 (2)	Zn2—O30—C30—O31	−4.7 (3)
O11'—C10'—N10'—C13'	−3 (4)	Zn2—O30—C30—N30	175.97 (13)
C10'—N10'—C11'—C12'	109.4 (19)	O31—C30—N30—C33	2.1 (3)
C13'—N10'—C11'—C12'	−78.7 (18)	O30—C30—N30—C33	−178.54 (17)
C10'—N10'—C13'—C14'	78 (3)	O31—C30—N30—C31	−177.74 (18)
C11'—N10'—C13'—C14'	−94 (2)	O30—C30—N30—C31	1.6 (3)
O20'—Zn2—O20—C20	63.0 (13)	C30—N30—C31—C32	−101.5 (2)
O10'—Zn2—O20—C20	23.9 (8)	C33—N30—C31—C32	78.6 (2)
O30—Zn2—O20—C20	−97.6 (5)	C30—N30—C33—C34	−94.0 (2)
O10—Zn2—O20—C20	20.4 (6)	C31—N30—C33—C34	85.8 (2)
Cl1—Zn2—O20—C20	142.2 (5)	O11—Zn1—N40—C41	−22.5 (6)
O11—Zn1—O21—C20	−97.5 (7)	O21—Zn1—N40—C41	94.6 (2)
O31—Zn1—O21—C20	33.3 (7)	O31—Zn1—N40—C41	−140.20 (14)
O21'—Zn1—O21—C20	62 (4)	O21'—Zn1—N40—C41	103.8 (6)
O11'—Zn1—O21—C20	−103.7 (9)	O11'—Zn1—N40—C41	−18.1 (17)
N40—Zn1—O21—C20	146.4 (6)	O11—Zn1—N40—C43	−150.0 (6)
Zn2—O20—C20—O21	19.3 (11)	O21—Zn1—N40—C43	−32.9 (2)
Zn2—O20—C20—N20	−162.1 (4)	O31—Zn1—N40—C43	92.35 (14)
Zn1—O21—C20—O20	17.3 (11)	O21'—Zn1—N40—C43	−23.6 (6)
Zn1—O21—C20—N20	−161.2 (5)	O11'—Zn1—N40—C43	−145.6 (17)
O20—C20—N20—C21	1.3 (9)	C43—N40—C41—C42	67.4 (2)
O21—C20—N20—C21	−180.0 (6)	Zn1—N40—C41—C42	−61.1 (2)
O20—C20—N20—C23	−179.8 (5)	C41—N40—C43—C44	170.60 (18)
O21—C20—N20—C23	−1.2 (9)	Zn1—N40—C43—C44	−61.2 (2)

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Chloro­(diethyl­amino)­tris(μ-diethyl­carbamato)­dizinc(II): an example of the generality of the threefold paddlewheel structure in carbamatozinc chemistry

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Chloro(diethylamino)tris(μ-diethylcarbamato)dizinc(II): an example of the generality of the threefold paddlewheel structure in carbamatozinc chemistry