research communications
(Acetonitrile-κN)aqua[N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine-κ4N,N′,N′′,N′′′]zinc(II) perchlorate
aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com
The structure of the title compound, [Zn(C14H18N4)(C2H3N)(H2O)](ClO4)2, contains a six-coordinate cation consisting of the tetradentate bispicen ligand, coordinated water, and coordinated acetonitrile, with the latter two ligands adopting a cis configuration. There are two formula units in the Both cations show almost identical structural features with the bispicen ligand adopting the more common cis-β conformation. One of the four perchlorate anions is disordered over two positions, with occupancies of 0.9090 (15) and 0.0910 (15). There is extensive inter-ionic hydrogen bonding between the perchlorate anions and O—H and N—H groups in the cations, including a bifurcated hydrogen bond between an N—H group and two O atoms of one perchlorate anion. As a result of this extended hydrogen-bond network, the ions are linked into a complex three-dimensional array.
Keywords: crystal structure; zinc(II); coordination complex; ethane-1,2-diamine.
CCDC reference: 1576091
1. Chemical context
One of the greatest challenges in synthetic chemistry is the selective conversion of non-activated C—H bonds to useful functional groups (Gunay & Theopold, 2010). Coordination complexes have been extensively explored due to their potential to catalyze such transformations. The ligand's around the metal ion determines the number and relative orientation of vacant coordination sites where terminal oxidants and/or substrates can bind. Installed steric bulk or substrate binding groups can either preclude certain molecules from accessing the active site (Chen & White, 2010) or attract compounds with specific shapes or functional groups (Das et al., 2006). These benefits rely upon the ability to understand, predict, and control the coordination geometry of the polydentate ligand.
The 1,2-bis(pyridin-2-ylmethyl)ethane-1,2-diamine (bispicen) ligand and other tetradentate ligands with reduced imine linkages have been observed to wrap around single transition metal ions in primarily two fashions: cis-α and cis-β (Scheme 2) (Chen et al., 2002). The cis-α, in which the two pyridine groups are trans to each other, has been the only conformation heretofore observed with bispicen and its methylated derivatives (Goodson et al., 1990, 1991). The cis-β conformation, in which the two pyridine groups are cis to each other, has been observed most often with ligands with propane-1,3-diamine backbones (England et al., 2007; Hureau et al., 2005a,b).
A third conformational possibility, alternately described as trans or planar (Scheme 2), has been structurally observed most commonly for tetradentate ligands with imine linkages, such as salens (Jacobsen et al., 1991). In tetradentate ligands with reduced imine linkages, the trans conformation has been observed rarely and only with ligands with either severely strained bridges or longer alkyl linkages between the (Mas-Ballesté et al., 2006). Consequently, the trans conformer is rarely mentioned as a plausible isomer in reactivity studies involving bispicen derivatives.
In view of the fact that ZnII is a d10 system and thus has a relatively plastic coordination environment it is of interest to determine which of the possible conformations the bispicen ligand adopts upon coordination to this metal ion. There is only one previous structural study of a bispicen derivative of Zn (Parajón-Costa et al., 2013). This study is in continuation of our past studies on the role of zinc in hydrolytic enzymes (Gultneh et al., 1996, 1999), in particular the role of Zn in lowering the pKa of coordinated water molecules.
2. Structural commentary
In the structure of the title compound (Fig. 1), the six-coordinate cation consists of the tetradentate bispicen ligand, coordinated water, and coordinated acetonitrile, with the latter two ligands adopting a cis conformation. There are two complete formula units in the Both cations show almost identical structural features with the bispicen ligand adopting the more common cis-β conformation, in which the two pyridine groups are cis to each other with the H2O and CH3CN ligands in trans position to the N—H groups. One of the four perchlorate anions is disordered over two positions with occupancies of 0.9090 (15) and 0.0910 (15). A related complex containing a [cis-Zn(bispicen)Cl(H2O)]+ cation and a [ZnCl4]2− anion has been published recently (Parajón-Costa et al., 2013). In contrast to previous studies, bond lengths for the two types of Zn—N bonds (Zn—Npy and Zn—NN—H) show very similar values, with the exception of those which are trans to the coordinated acetonitrile (Table 1). The latter are significantly longer [2.2056 (7) and 2.2066 (7) Å]. Interestingly, Zn—OH2 bond lengths are relatively short [2.1333 (7) and 2.1279 (7) Å] reflecting a strong Zn—O bond. Further studies will be made to see the effect of this on the pKa of the coordinated water. There is extensive inter-ionic hydrogen bonding (Table 2) between the perchlorate anions and O—H and N—H groups in the cations including a bifurcated hydrogen bond between an N—H group and two O atoms of one perchlorate anion. As a result of this extended hydrogen-bond network the ions are linked into a complex three-dimensional array.
|
3. Supramolecular features
There is a complex array of hydrogen bonds between the O—H and N—H groups in the cations and the O atoms of the anions. In addition, there are weak C—H⋯O interactions between the CH3 groups of the coordinated acetonitrile moieties and the adjoining O atoms of the perchlorate anions. These link the ions into a complex three-dimensional array (Fig. 2).
4. Database survey
A survey of the Cambridge Structural Database (Groom et al., 2016) for complexes of bispicen with Zn gave only one hit (Parajón-Costa et al., 2013). This structure contained a [cis-Zn(bispicen)Cl(H2O)]+ cation and a [ZnCl4]2− anion.
5. Synthesis and crystallization
Pyridine-2-carbaldehyde (2.3996 g, 0.0022 mol) was added to a reaction flask and dissolved in 50 ml methanol. Ethylenediamine (0.6732 g, 0.0012 mol) was added to the solution. The mixture was stirred for 3 d before refluxing the reaction for 1 h. The contents of the reaction flask were cooled to 268 K. 4 equivalents of NaBH4 (1.6646 g, 0.0044 mol) were added to the reaction mixture which was then allowed to reach room temperature. The mixture was stirred overnight. Methanol was evaporated under reduced pressure. The contents were redissolved in water (50 ml) before being extracted with chloroform (4 × 50 ml). Moisture was removed using anhydrous MgSO4. Chloroform was evaporated under reduced pressure producing the ligand as a brown oil (yield 68%). The zinc(II) complex was prepared by reacting 0.4356 g (0.0018 mol) of the ligand in 50 ml acetonitrile with Zn(ClO4)2·6H2O (0.4251 g, 0.0018 mol). The mixture was stirred at room temperature overnight and layered with 50 ml diethyl ether. The container was sealed and diethylether allowed to diffuse into the solution for 3 d to give yellow crystals which were filtered and dried [yield based on Zn(ClO4)2: 55%].
6. Refinement
Crystal data, data collection and structure . H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H ranging from 0.95 to 0.99 Å and N—H at 1.00 Å. Displacement parameters were fixed to Uiso(H) = xUeq(C), where x = 1.5 for methyl H atoms and 1.2 for all other C-bound and N-bound H atoms. H atoms attached to water were refined isotropically. One of the four perchlorate anions is disordered over two positions with occupancies of 0.9090 (15) and 0.0910 (15), and were constrained to have similar displacement and metrical parameters.
details are summarized in Table 3
|
Supporting information
CCDC reference: 1576091
https://doi.org/10.1107/S2056989017013603/im2479sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017013603/im2479Isup2.hkl
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Zn(C14H18N4)(C2H3N)(H2O)](ClO4)2 | Z = 4 |
Mr = 565.66 | F(000) = 1160 |
Triclinic, P1 | Dx = 1.704 Mg m−3 |
a = 8.2959 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3169 (4) Å | Cell parameters from 9442 reflections |
c = 27.7884 (9) Å | θ = 3.2–61.9° |
α = 92.969 (1)° | µ = 1.42 mm−1 |
β = 98.241 (1)° | T = 100 K |
γ = 109.620 (1)° | Block, colourless |
V = 2204.36 (14) Å3 | 0.45 × 0.41 × 0.29 mm |
Bruker Quest CCD diffractometer | 31022 reflections with I > 2σ(I) |
ω scans | Rint = 0.047 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 49.2°, θmin = 2.3° |
Tmin = 0.453, Tmax = 0.753 | h = −9→9 |
37729 measured reflections | k = −12→12 |
37729 independent reflections | l = −32→33 |
Refinement on F2 | 56 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0391P)2 + 1.0144P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.006 |
37729 reflections | Δρmax = 2.24 e Å−3 |
636 parameters | Δρmin = −1.15 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.83273 (2) | 0.76731 (2) | 0.37527 (2) | 0.01022 (2) | |
O1W | 0.61524 (9) | 0.81617 (8) | 0.34185 (2) | 0.01495 (10) | |
H1W1 | 0.611 (2) | 0.8958 (14) | 0.3465 (7) | 0.021 (4)* | |
H1W2 | 0.5198 (19) | 0.7649 (16) | 0.3439 (7) | 0.022 (4)* | |
N1A | 0.71985 (8) | 0.70563 (8) | 0.43995 (2) | 0.01171 (9) | |
N2A | 1.03060 (9) | 0.70258 (8) | 0.41604 (3) | 0.01261 (10) | |
H2AB | 1.0721 | 0.6483 | 0.3929 | 0.015* | |
N3A | 0.99210 (9) | 0.97233 (8) | 0.41415 (2) | 0.01183 (9) | |
H3AB | 0.9157 | 1.0157 | 0.4283 | 0.014* | |
N4A | 0.99441 (9) | 0.85294 (8) | 0.32333 (2) | 0.01277 (10) | |
N5A | 0.71429 (11) | 0.57128 (9) | 0.33332 (3) | 0.01715 (12) | |
C1A | 0.58572 (10) | 0.73342 (10) | 0.45424 (3) | 0.01395 (12) | |
H1AA | 0.5210 | 0.7731 | 0.4325 | 0.017* | |
C2A | 0.53812 (11) | 0.70639 (10) | 0.49963 (3) | 0.01520 (13) | |
H2AA | 0.4410 | 0.7253 | 0.5084 | 0.018* | |
C3A | 0.63487 (11) | 0.65113 (10) | 0.53211 (3) | 0.01514 (13) | |
H3AA | 0.6058 | 0.6325 | 0.5635 | 0.018* | |
C4A | 0.77454 (11) | 0.62379 (10) | 0.51771 (3) | 0.01419 (12) | |
H4AA | 0.8440 | 0.5874 | 0.5393 | 0.017* | |
C5A | 0.81176 (10) | 0.65040 (9) | 0.47104 (3) | 0.01169 (10) | |
C6A | 0.95559 (11) | 0.61389 (10) | 0.45279 (3) | 0.01427 (12) | |
H6AA | 1.0483 | 0.6229 | 0.4808 | 0.017* | |
H6AB | 0.9094 | 0.5161 | 0.4383 | 0.017* | |
C7A | 1.17523 (10) | 0.83110 (10) | 0.43644 (3) | 0.01500 (12) | |
H7AA | 1.2467 | 0.8654 | 0.4110 | 0.018* | |
H7AB | 1.2500 | 0.8113 | 0.4640 | 0.018* | |
C8A | 1.10825 (11) | 0.94212 (10) | 0.45419 (3) | 0.01437 (12) | |
H8AA | 1.0441 | 0.9106 | 0.4813 | 0.017* | |
H8AB | 1.2077 | 1.0277 | 0.4669 | 0.017* | |
C9A | 1.08674 (12) | 1.06278 (9) | 0.38040 (3) | 0.01483 (12) | |
H9AA | 1.2040 | 1.1197 | 0.3980 | 0.018* | |
H9AB | 1.0248 | 1.1264 | 0.3701 | 0.018* | |
C10A | 1.10454 (10) | 0.98339 (9) | 0.33561 (3) | 0.01292 (11) | |
C11A | 1.22877 (12) | 1.04752 (11) | 0.30741 (3) | 0.01845 (15) | |
H11A | 1.3072 | 1.1392 | 0.3173 | 0.022* | |
C12A | 1.23620 (13) | 0.97543 (13) | 0.26464 (4) | 0.02126 (17) | |
H12A | 1.3189 | 1.0175 | 0.2446 | 0.026* | |
C13A | 1.12063 (13) | 0.84058 (12) | 0.25154 (3) | 0.01897 (15) | |
H13A | 1.1220 | 0.7894 | 0.2223 | 0.023* | |
C14A | 1.00344 (12) | 0.78261 (10) | 0.28217 (3) | 0.01595 (13) | |
H14A | 0.9266 | 0.6897 | 0.2738 | 0.019* | |
C15A | 0.66602 (11) | 0.46620 (9) | 0.31015 (3) | 0.01465 (12) | |
C16A | 0.60567 (15) | 0.33475 (10) | 0.27988 (3) | 0.01905 (15) | |
H16A | 0.4855 | 0.3148 | 0.2638 | 0.029* | |
H16B | 0.6110 | 0.2612 | 0.3003 | 0.029* | |
H16C | 0.6797 | 0.3394 | 0.2551 | 0.029* | |
Zn2 | 0.17061 (2) | 0.21312 (2) | 0.12948 (2) | 0.01100 (2) | |
O2W | 0.38318 (9) | 0.15838 (8) | 0.16247 (2) | 0.01486 (10) | |
H2W1 | 0.479 (2) | 0.2123 (17) | 0.1601 (7) | 0.030 (5)* | |
H2W2 | 0.386 (2) | 0.0810 (14) | 0.1559 (6) | 0.019 (4)* | |
N1B | 0.28232 (9) | 0.27927 (8) | 0.06607 (2) | 0.01196 (10) | |
N2B | −0.02412 (9) | 0.28556 (9) | 0.09126 (3) | 0.01434 (11) | |
H2BB | −0.0633 | 0.3385 | 0.1155 | 0.017* | |
N3B | 0.00700 (9) | 0.01205 (8) | 0.08839 (3) | 0.01278 (10) | |
H3BB | 0.0815 | −0.0307 | 0.0730 | 0.015* | |
N4B | 0.00625 (9) | 0.12413 (8) | 0.18045 (3) | 0.01389 (11) | |
N5B | 0.29347 (11) | 0.40678 (9) | 0.17350 (3) | 0.01795 (13) | |
C1B | 0.41515 (10) | 0.25042 (10) | 0.05142 (3) | 0.01366 (12) | |
H1BA | 0.4762 | 0.2062 | 0.0724 | 0.016* | |
C2B | 0.46654 (11) | 0.28262 (10) | 0.00690 (3) | 0.01498 (13) | |
H2BA | 0.5621 | 0.2622 | −0.0023 | 0.018* | |
C3B | 0.37530 (12) | 0.34545 (10) | −0.02411 (3) | 0.01559 (13) | |
H3BA | 0.4072 | 0.3682 | −0.0549 | 0.019* | |
C4B | 0.23719 (12) | 0.37432 (10) | −0.00934 (3) | 0.01569 (13) | |
H4BA | 0.1719 | 0.4159 | −0.0301 | 0.019* | |
C5B | 0.19527 (10) | 0.34154 (9) | 0.03642 (3) | 0.01292 (11) | |
C6B | 0.05258 (12) | 0.37796 (10) | 0.05555 (4) | 0.01661 (13) | |
H6BA | 0.1004 | 0.4746 | 0.0712 | 0.020* | |
H6BB | −0.0396 | 0.3723 | 0.0278 | 0.020* | |
C7B | −0.17097 (11) | 0.15995 (11) | 0.06975 (4) | 0.01697 (14) | |
H7BA | −0.2450 | 0.1837 | 0.0430 | 0.020* | |
H7BB | −0.2424 | 0.1238 | 0.0950 | 0.020* | |
C8B | −0.10838 (11) | 0.04847 (10) | 0.04981 (3) | 0.01612 (13) | |
H8BA | −0.2099 | −0.0352 | 0.0365 | 0.019* | |
H8BB | −0.0448 | 0.0819 | 0.0228 | 0.019* | |
C9B | −0.08761 (12) | −0.08171 (10) | 0.12122 (3) | 0.01626 (13) | |
H9BA | −0.0259 | −0.1461 | 0.1306 | 0.020* | |
H9BB | −0.2050 | −0.1375 | 0.1034 | 0.020* | |
C10B | −0.10482 (11) | −0.00548 (10) | 0.16698 (3) | 0.01407 (12) | |
C11B | −0.23001 (13) | −0.07162 (12) | 0.19458 (4) | 0.02008 (16) | |
H11B | −0.3085 | −0.1630 | 0.1841 | 0.024* | |
C12B | −0.23822 (14) | −0.00165 (13) | 0.23783 (4) | 0.02261 (18) | |
H12B | −0.3215 | −0.0450 | 0.2575 | 0.027* | |
C13B | −0.12295 (13) | 0.13227 (12) | 0.25180 (3) | 0.01974 (16) | |
H13B | −0.1257 | 0.1821 | 0.2812 | 0.024* | |
C14B | −0.00359 (12) | 0.19202 (11) | 0.22199 (3) | 0.01707 (14) | |
H14B | 0.0741 | 0.2843 | 0.2312 | 0.020* | |
C15B | 0.34115 (11) | 0.51392 (10) | 0.19532 (3) | 0.01525 (12) | |
C16B | 0.39955 (14) | 0.64762 (10) | 0.22374 (4) | 0.01918 (15) | |
H16D | 0.3243 | 0.6457 | 0.2480 | 0.029* | |
H16E | 0.3947 | 0.7185 | 0.2020 | 0.029* | |
H16F | 0.5193 | 0.6693 | 0.2404 | 0.029* | |
Cl1 | 0.33629 (2) | −0.17248 (2) | 0.09748 (2) | 0.01340 (3) | |
O11 | 0.30474 (11) | −0.12439 (8) | 0.14429 (3) | 0.01993 (13) | |
O12 | 0.37512 (14) | −0.29685 (10) | 0.10216 (4) | 0.02729 (17) | |
O13 | 0.47992 (13) | −0.06661 (11) | 0.08384 (4) | 0.0317 (2) | |
O14 | 0.18341 (12) | −0.19854 (12) | 0.06120 (3) | 0.0314 (2) | |
Cl2 | 0.66222 (2) | 1.15399 (2) | 0.40344 (2) | 0.01185 (3) | |
O21 | 0.62121 (14) | 1.27698 (10) | 0.39746 (3) | 0.02598 (17) | |
O22 | 0.68767 (11) | 1.10012 (8) | 0.35669 (2) | 0.01847 (12) | |
O23 | 0.81983 (11) | 1.18512 (11) | 0.43829 (3) | 0.02691 (17) | |
O24 | 0.52286 (13) | 1.05033 (11) | 0.42000 (4) | 0.0321 (2) | |
Cl3 | 0.21799 (3) | 0.50962 (2) | −0.16092 (2) | 0.01582 (3) | |
O31 | 0.27818 (11) | 0.65914 (9) | −0.16224 (4) | 0.02509 (16) | |
O32 | 0.26294 (13) | 0.44580 (11) | −0.20132 (4) | 0.0314 (2) | |
O33 | 0.03501 (14) | 0.46092 (13) | −0.16261 (6) | 0.0477 (3) | |
O34 | 0.3044 (2) | 0.48292 (17) | −0.11636 (4) | 0.0603 (4) | |
Cl4 | 1.18034 (5) | 0.48638 (4) | 0.33410 (2) | 0.01448 (5) | 0.9090 (15) |
O41 | 1.28183 (13) | 0.63107 (11) | 0.35110 (4) | 0.0286 (2) | 0.9090 (15) |
O42 | 1.06676 (17) | 0.43235 (13) | 0.36849 (4) | 0.0339 (3) | 0.9090 (15) |
O43 | 1.07584 (18) | 0.47935 (13) | 0.28758 (4) | 0.0358 (3) | 0.9090 (15) |
O44 | 1.29117 (16) | 0.40816 (15) | 0.32951 (7) | 0.0499 (4) | 0.9090 (15) |
Cl4A | 1.2271 (6) | 0.4988 (5) | 0.33959 (14) | 0.0173 (6) | 0.0910 (15) |
O41A | 1.3201 (11) | 0.4703 (10) | 0.3811 (3) | 0.0286 (2) | 0.0910 (15) |
O42A | 1.0388 (13) | 0.4473 (12) | 0.3392 (4) | 0.0339 (3) | 0.0910 (15) |
O43A | 1.280 (2) | 0.6441 (11) | 0.3365 (4) | 0.0358 (3) | 0.0910 (15) |
O44A | 1.2617 (16) | 0.4390 (15) | 0.2955 (5) | 0.0499 (4) | 0.0910 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.00995 (3) | 0.01079 (4) | 0.00945 (3) | 0.00291 (3) | 0.00217 (2) | 0.00021 (2) |
O1W | 0.0134 (2) | 0.0150 (3) | 0.0161 (2) | 0.00531 (19) | 0.00066 (17) | 0.00013 (19) |
N1A | 0.0103 (2) | 0.0137 (3) | 0.0118 (2) | 0.00480 (18) | 0.00263 (16) | 0.00136 (18) |
N2A | 0.0126 (2) | 0.0133 (3) | 0.0137 (2) | 0.00588 (19) | 0.00452 (18) | 0.00143 (19) |
N3A | 0.0122 (2) | 0.0120 (3) | 0.0117 (2) | 0.00456 (18) | 0.00275 (17) | 0.00024 (18) |
N4A | 0.0133 (2) | 0.0135 (3) | 0.0111 (2) | 0.00355 (19) | 0.00376 (17) | 0.00090 (19) |
N5A | 0.0180 (3) | 0.0136 (3) | 0.0177 (3) | 0.0034 (2) | 0.0025 (2) | −0.0018 (2) |
C1A | 0.0117 (2) | 0.0181 (3) | 0.0132 (2) | 0.0066 (2) | 0.0026 (2) | 0.0009 (2) |
C2A | 0.0131 (3) | 0.0183 (4) | 0.0145 (3) | 0.0051 (2) | 0.0049 (2) | 0.0000 (2) |
C3A | 0.0158 (3) | 0.0153 (3) | 0.0131 (2) | 0.0029 (2) | 0.0051 (2) | 0.0007 (2) |
C4A | 0.0148 (3) | 0.0144 (3) | 0.0135 (2) | 0.0046 (2) | 0.0035 (2) | 0.0033 (2) |
C5A | 0.0113 (2) | 0.0116 (3) | 0.0127 (2) | 0.0041 (2) | 0.00288 (18) | 0.0020 (2) |
C6A | 0.0145 (3) | 0.0142 (3) | 0.0171 (3) | 0.0076 (2) | 0.0049 (2) | 0.0045 (2) |
C7A | 0.0099 (2) | 0.0168 (3) | 0.0187 (3) | 0.0051 (2) | 0.0023 (2) | 0.0030 (3) |
C8A | 0.0135 (3) | 0.0137 (3) | 0.0139 (2) | 0.0036 (2) | −0.0004 (2) | −0.0005 (2) |
C9A | 0.0178 (3) | 0.0105 (3) | 0.0159 (3) | 0.0035 (2) | 0.0057 (2) | 0.0013 (2) |
C10A | 0.0123 (2) | 0.0136 (3) | 0.0128 (2) | 0.0036 (2) | 0.00367 (19) | 0.0027 (2) |
C11A | 0.0172 (3) | 0.0194 (4) | 0.0182 (3) | 0.0031 (3) | 0.0079 (3) | 0.0049 (3) |
C12A | 0.0199 (4) | 0.0275 (5) | 0.0178 (3) | 0.0067 (3) | 0.0104 (3) | 0.0061 (3) |
C13A | 0.0210 (3) | 0.0264 (5) | 0.0127 (3) | 0.0106 (3) | 0.0071 (2) | 0.0024 (3) |
C14A | 0.0175 (3) | 0.0184 (4) | 0.0118 (2) | 0.0056 (3) | 0.0044 (2) | −0.0004 (2) |
C15A | 0.0168 (3) | 0.0122 (3) | 0.0139 (3) | 0.0035 (2) | 0.0034 (2) | 0.0007 (2) |
C16A | 0.0287 (4) | 0.0117 (3) | 0.0144 (3) | 0.0040 (3) | 0.0043 (3) | −0.0005 (2) |
Zn2 | 0.01021 (3) | 0.01191 (4) | 0.00994 (3) | 0.00248 (3) | 0.00271 (2) | −0.00051 (3) |
O2W | 0.0141 (2) | 0.0145 (3) | 0.0153 (2) | 0.00460 (19) | 0.00156 (17) | 0.00032 (19) |
N1B | 0.0109 (2) | 0.0138 (3) | 0.0114 (2) | 0.00427 (18) | 0.00268 (16) | 0.00160 (18) |
N2B | 0.0135 (2) | 0.0148 (3) | 0.0167 (2) | 0.0067 (2) | 0.00503 (19) | 0.0004 (2) |
N3B | 0.0122 (2) | 0.0128 (3) | 0.0132 (2) | 0.00396 (19) | 0.00343 (17) | −0.00034 (19) |
N4B | 0.0135 (2) | 0.0156 (3) | 0.0123 (2) | 0.0037 (2) | 0.00466 (18) | 0.0001 (2) |
N5B | 0.0182 (3) | 0.0147 (3) | 0.0184 (3) | 0.0034 (2) | 0.0023 (2) | −0.0026 (2) |
C1B | 0.0124 (2) | 0.0177 (3) | 0.0118 (2) | 0.0061 (2) | 0.00272 (19) | 0.0019 (2) |
C2B | 0.0137 (3) | 0.0192 (4) | 0.0123 (2) | 0.0053 (2) | 0.0041 (2) | 0.0012 (2) |
C3B | 0.0167 (3) | 0.0167 (4) | 0.0117 (2) | 0.0033 (2) | 0.0031 (2) | 0.0022 (2) |
C4B | 0.0162 (3) | 0.0156 (3) | 0.0150 (3) | 0.0048 (2) | 0.0023 (2) | 0.0046 (2) |
C5B | 0.0119 (2) | 0.0125 (3) | 0.0143 (2) | 0.0041 (2) | 0.0022 (2) | 0.0023 (2) |
C6B | 0.0163 (3) | 0.0150 (3) | 0.0219 (3) | 0.0084 (3) | 0.0058 (3) | 0.0050 (3) |
C7B | 0.0100 (2) | 0.0192 (4) | 0.0218 (3) | 0.0054 (2) | 0.0023 (2) | 0.0023 (3) |
C8B | 0.0141 (3) | 0.0157 (3) | 0.0154 (3) | 0.0027 (2) | −0.0006 (2) | −0.0012 (2) |
C9B | 0.0174 (3) | 0.0122 (3) | 0.0182 (3) | 0.0027 (2) | 0.0063 (2) | 0.0006 (2) |
C10B | 0.0128 (3) | 0.0155 (3) | 0.0144 (3) | 0.0045 (2) | 0.0045 (2) | 0.0030 (2) |
C11B | 0.0177 (3) | 0.0209 (4) | 0.0202 (3) | 0.0021 (3) | 0.0088 (3) | 0.0057 (3) |
C12B | 0.0205 (4) | 0.0302 (5) | 0.0194 (3) | 0.0078 (3) | 0.0113 (3) | 0.0085 (3) |
C13B | 0.0209 (4) | 0.0276 (5) | 0.0140 (3) | 0.0105 (3) | 0.0080 (3) | 0.0038 (3) |
C14B | 0.0184 (3) | 0.0202 (4) | 0.0128 (3) | 0.0059 (3) | 0.0059 (2) | −0.0001 (2) |
C15B | 0.0161 (3) | 0.0132 (3) | 0.0156 (3) | 0.0039 (2) | 0.0032 (2) | 0.0000 (2) |
C16B | 0.0255 (4) | 0.0125 (3) | 0.0177 (3) | 0.0040 (3) | 0.0054 (3) | −0.0012 (3) |
Cl1 | 0.01268 (6) | 0.01273 (7) | 0.01505 (6) | 0.00419 (5) | 0.00425 (5) | 0.00015 (5) |
O11 | 0.0276 (3) | 0.0176 (3) | 0.0170 (2) | 0.0092 (3) | 0.0090 (2) | −0.0001 (2) |
O12 | 0.0400 (5) | 0.0205 (4) | 0.0306 (4) | 0.0195 (4) | 0.0129 (3) | 0.0039 (3) |
O13 | 0.0281 (4) | 0.0244 (4) | 0.0381 (5) | −0.0021 (3) | 0.0190 (4) | 0.0039 (4) |
O14 | 0.0241 (4) | 0.0441 (6) | 0.0252 (4) | 0.0174 (4) | −0.0069 (3) | −0.0100 (4) |
Cl2 | 0.01223 (6) | 0.01228 (7) | 0.01196 (6) | 0.00475 (5) | 0.00369 (5) | 0.00156 (5) |
O21 | 0.0431 (5) | 0.0244 (4) | 0.0232 (3) | 0.0248 (4) | 0.0125 (3) | 0.0065 (3) |
O22 | 0.0265 (3) | 0.0180 (3) | 0.0133 (2) | 0.0101 (2) | 0.0060 (2) | −0.0003 (2) |
O23 | 0.0217 (3) | 0.0375 (5) | 0.0204 (3) | 0.0139 (3) | −0.0057 (2) | −0.0068 (3) |
O24 | 0.0290 (4) | 0.0255 (4) | 0.0368 (5) | −0.0031 (3) | 0.0195 (4) | 0.0047 (4) |
Cl3 | 0.01840 (8) | 0.01536 (8) | 0.01327 (6) | 0.00440 (6) | 0.00522 (5) | 0.00059 (6) |
O31 | 0.0211 (3) | 0.0159 (3) | 0.0381 (4) | 0.0051 (2) | 0.0087 (3) | 0.0000 (3) |
O32 | 0.0294 (4) | 0.0306 (5) | 0.0326 (4) | 0.0080 (3) | 0.0116 (3) | −0.0113 (4) |
O33 | 0.0229 (4) | 0.0339 (6) | 0.0813 (10) | −0.0011 (4) | 0.0264 (5) | −0.0116 (6) |
O34 | 0.0904 (11) | 0.0514 (8) | 0.0264 (5) | 0.0168 (8) | −0.0155 (6) | 0.0158 (5) |
Cl4 | 0.01332 (12) | 0.01540 (11) | 0.01515 (10) | 0.00505 (11) | 0.00474 (10) | −0.00139 (8) |
O41 | 0.0188 (3) | 0.0219 (4) | 0.0380 (5) | −0.0011 (3) | 0.0079 (4) | −0.0122 (4) |
O42 | 0.0441 (6) | 0.0305 (5) | 0.0285 (4) | 0.0074 (4) | 0.0227 (4) | 0.0075 (4) |
O43 | 0.0524 (7) | 0.0308 (6) | 0.0174 (3) | 0.0114 (5) | −0.0060 (4) | −0.0023 (3) |
O44 | 0.0274 (5) | 0.0380 (7) | 0.0897 (12) | 0.0219 (5) | 0.0089 (6) | −0.0136 (7) |
Cl4A | 0.0147 (13) | 0.0239 (15) | 0.0141 (10) | 0.0072 (13) | 0.0038 (10) | 0.0015 (9) |
O41A | 0.0188 (3) | 0.0219 (4) | 0.0380 (5) | −0.0011 (3) | 0.0079 (4) | −0.0122 (4) |
O42A | 0.0441 (6) | 0.0305 (5) | 0.0285 (4) | 0.0074 (4) | 0.0227 (4) | 0.0075 (4) |
O43A | 0.0524 (7) | 0.0308 (6) | 0.0174 (3) | 0.0114 (5) | −0.0060 (4) | −0.0023 (3) |
O44A | 0.0274 (5) | 0.0380 (7) | 0.0897 (12) | 0.0219 (5) | 0.0089 (6) | −0.0136 (7) |
Zn1—N5A | 2.1231 (8) | N2B—C6B | 1.4730 (12) |
Zn1—O1W | 2.1333 (7) | N2B—C7B | 1.4737 (12) |
Zn1—N4A | 2.1341 (7) | N2B—H2BB | 1.0000 |
Zn1—N2A | 2.1692 (7) | N3B—C9B | 1.4734 (11) |
Zn1—N1A | 2.1707 (7) | N3B—C8B | 1.4818 (12) |
Zn1—N3A | 2.2056 (7) | N3B—H3BB | 1.0000 |
O1W—H1W1 | 0.839 (13) | N4B—C10B | 1.3413 (12) |
O1W—H1W2 | 0.803 (13) | N4B—C14B | 1.3458 (11) |
N1A—C5A | 1.3441 (11) | N5B—C15B | 1.1464 (12) |
N1A—C1A | 1.3443 (10) | C1B—C2B | 1.3861 (11) |
N2A—C6A | 1.4711 (11) | C1B—H1BA | 0.9500 |
N2A—C7A | 1.4757 (12) | C2B—C3B | 1.3915 (13) |
N2A—H2AB | 1.0000 | C2B—H2BA | 0.9500 |
N3A—C9A | 1.4754 (11) | C3B—C4B | 1.3861 (13) |
N3A—C8A | 1.4811 (11) | C3B—H3BA | 0.9500 |
N3A—H3AB | 1.0000 | C4B—C5B | 1.3945 (12) |
N4A—C10A | 1.3415 (11) | C4B—H4BA | 0.9500 |
N4A—C14A | 1.3476 (11) | C5B—C6B | 1.5111 (12) |
N5A—C15A | 1.1457 (12) | C6B—H6BA | 0.9900 |
C1A—C2A | 1.3892 (11) | C6B—H6BB | 0.9900 |
C1A—H1AA | 0.9500 | C7B—C8B | 1.5222 (14) |
C2A—C3A | 1.3917 (14) | C7B—H7BA | 0.9900 |
C2A—H2AA | 0.9500 | C7B—H7BB | 0.9900 |
C3A—C4A | 1.3867 (13) | C8B—H8BA | 0.9900 |
C3A—H3AA | 0.9500 | C8B—H8BB | 0.9900 |
C4A—C5A | 1.3954 (11) | C9B—C10B | 1.5099 (12) |
C4A—H4AA | 0.9500 | C9B—H9BA | 0.9900 |
C5A—C6A | 1.5094 (11) | C9B—H9BB | 0.9900 |
C6A—H6AA | 0.9900 | C10B—C11B | 1.3925 (12) |
C6A—H6AB | 0.9900 | C11B—C12B | 1.3917 (15) |
C7A—C8A | 1.5204 (13) | C11B—H11B | 0.9500 |
C7A—H7AA | 0.9900 | C12B—C13B | 1.3873 (17) |
C7A—H7AB | 0.9900 | C12B—H12B | 0.9500 |
C8A—H8AA | 0.9900 | C13B—C14B | 1.3874 (13) |
C8A—H8AB | 0.9900 | C13B—H13B | 0.9500 |
C9A—C10A | 1.5067 (12) | C14B—H14B | 0.9500 |
C9A—H9AA | 0.9900 | C15B—C16B | 1.4456 (13) |
C9A—H9AB | 0.9900 | C16B—H16D | 0.9800 |
C10A—C11A | 1.3933 (12) | C16B—H16E | 0.9800 |
C11A—C12A | 1.3891 (14) | C16B—H16F | 0.9800 |
C11A—H11A | 0.9500 | Cl1—O12 | 1.4317 (9) |
C12A—C13A | 1.3925 (16) | Cl1—O13 | 1.4334 (9) |
C12A—H12A | 0.9500 | Cl1—O14 | 1.4399 (9) |
C13A—C14A | 1.3880 (12) | Cl1—O11 | 1.4577 (7) |
C13A—H13A | 0.9500 | Cl2—O21 | 1.4313 (9) |
C14A—H14A | 0.9500 | Cl2—O24 | 1.4371 (9) |
C15A—C16A | 1.4499 (13) | Cl2—O23 | 1.4399 (8) |
C16A—H16A | 0.9800 | Cl2—O22 | 1.4574 (7) |
C16A—H16B | 0.9800 | Cl3—O33 | 1.4227 (10) |
C16A—H16C | 0.9800 | Cl3—O34 | 1.4272 (11) |
Zn2—O2W | 2.1279 (7) | Cl3—O32 | 1.4289 (9) |
Zn2—N5B | 2.1328 (8) | Cl3—O31 | 1.4575 (9) |
Zn2—N4B | 2.1345 (7) | Cl4—O44 | 1.4263 (12) |
Zn2—N1B | 2.1440 (7) | Cl4—O43 | 1.4334 (11) |
Zn2—N2B | 2.1674 (8) | Cl4—O42 | 1.4396 (10) |
Zn2—N3B | 2.2066 (7) | Cl4—O41 | 1.4592 (11) |
O2W—H2W1 | 0.818 (13) | Cl4A—O41A | 1.394 (10) |
O2W—H2W2 | 0.817 (13) | Cl4A—O43A | 1.425 (11) |
N1B—C1B | 1.3436 (11) | Cl4A—O44A | 1.451 (11) |
N1B—C5B | 1.3451 (11) | Cl4A—O42A | 1.470 (10) |
N5A—Zn1—O1W | 86.48 (3) | Zn2—O2W—H2W1 | 115.0 (14) |
N5A—Zn1—N4A | 93.75 (3) | Zn2—O2W—H2W2 | 120.0 (12) |
O1W—Zn1—N4A | 95.55 (3) | H2W1—O2W—H2W2 | 106.0 (16) |
N5A—Zn1—N2A | 92.19 (3) | C1B—N1B—C5B | 118.86 (7) |
O1W—Zn1—N2A | 172.06 (3) | C1B—N1B—Zn2 | 126.05 (6) |
N4A—Zn1—N2A | 92.34 (3) | C5B—N1B—Zn2 | 114.63 (5) |
N5A—Zn1—N1A | 96.07 (3) | C6B—N2B—C7B | 114.68 (7) |
O1W—Zn1—N1A | 93.28 (3) | C6B—N2B—Zn2 | 109.28 (5) |
N4A—Zn1—N1A | 167.17 (3) | C7B—N2B—Zn2 | 105.72 (6) |
N2A—Zn1—N1A | 79.06 (3) | C6B—N2B—H2BB | 109.0 |
N5A—Zn1—N3A | 171.11 (3) | C7B—N2B—H2BB | 109.0 |
O1W—Zn1—N3A | 99.00 (3) | Zn2—N2B—H2BB | 109.0 |
N4A—Zn1—N3A | 78.83 (3) | C9B—N3B—C8B | 113.46 (7) |
N2A—Zn1—N3A | 83.32 (3) | C9B—N3B—Zn2 | 110.38 (5) |
N1A—Zn1—N3A | 90.62 (3) | C8B—N3B—Zn2 | 103.99 (6) |
Zn1—O1W—H1W1 | 121.3 (12) | C9B—N3B—H3BB | 109.6 |
Zn1—O1W—H1W2 | 118.1 (13) | C8B—N3B—H3BB | 109.6 |
H1W1—O1W—H1W2 | 104.6 (15) | Zn2—N3B—H3BB | 109.6 |
C5A—N1A—C1A | 118.48 (7) | C10B—N4B—C14B | 118.88 (7) |
C5A—N1A—Zn1 | 113.99 (5) | C10B—N4B—Zn2 | 115.92 (5) |
C1A—N1A—Zn1 | 126.90 (6) | C14B—N4B—Zn2 | 124.92 (6) |
C6A—N2A—C7A | 114.60 (7) | C15B—N5B—Zn2 | 171.64 (8) |
C6A—N2A—Zn1 | 109.42 (5) | N1B—C1B—C2B | 122.58 (8) |
C7A—N2A—Zn1 | 105.92 (5) | N1B—C1B—H1BA | 118.7 |
C6A—N2A—H2AB | 108.9 | C2B—C1B—H1BA | 118.7 |
C7A—N2A—H2AB | 108.9 | C1B—C2B—C3B | 118.67 (8) |
Zn1—N2A—H2AB | 108.9 | C1B—C2B—H2BA | 120.7 |
C9A—N3A—C8A | 113.24 (7) | C3B—C2B—H2BA | 120.7 |
C9A—N3A—Zn1 | 110.38 (5) | C4B—C3B—C2B | 118.97 (8) |
C8A—N3A—Zn1 | 104.29 (5) | C4B—C3B—H3BA | 120.5 |
C9A—N3A—H3AB | 109.6 | C2B—C3B—H3BA | 120.5 |
C8A—N3A—H3AB | 109.6 | C3B—C4B—C5B | 119.14 (8) |
Zn1—N3A—H3AB | 109.6 | C3B—C4B—H4BA | 120.4 |
C10A—N4A—C14A | 118.80 (7) | C5B—C4B—H4BA | 120.4 |
C10A—N4A—Zn1 | 115.96 (5) | N1B—C5B—C4B | 121.76 (8) |
C14A—N4A—Zn1 | 124.98 (6) | N1B—C5B—C6B | 116.85 (7) |
C15A—N5A—Zn1 | 173.47 (8) | C4B—C5B—C6B | 121.37 (8) |
N1A—C1A—C2A | 122.56 (8) | N2B—C6B—C5B | 112.39 (7) |
N1A—C1A—H1AA | 118.7 | N2B—C6B—H6BA | 109.1 |
C2A—C1A—H1AA | 118.7 | C5B—C6B—H6BA | 109.1 |
C1A—C2A—C3A | 118.96 (8) | N2B—C6B—H6BB | 109.1 |
C1A—C2A—H2AA | 120.5 | C5B—C6B—H6BB | 109.1 |
C3A—C2A—H2AA | 120.5 | H6BA—C6B—H6BB | 107.9 |
C4A—C3A—C2A | 118.64 (7) | N2B—C7B—C8B | 111.43 (7) |
C4A—C3A—H3AA | 120.7 | N2B—C7B—H7BA | 109.3 |
C2A—C3A—H3AA | 120.7 | C8B—C7B—H7BA | 109.3 |
C3A—C4A—C5A | 119.11 (8) | N2B—C7B—H7BB | 109.3 |
C3A—C4A—H4AA | 120.4 | C8B—C7B—H7BB | 109.3 |
C5A—C4A—H4AA | 120.4 | H7BA—C7B—H7BB | 108.0 |
N1A—C5A—C4A | 122.22 (7) | N3B—C8B—C7B | 111.31 (7) |
N1A—C5A—C6A | 116.98 (7) | N3B—C8B—H8BA | 109.4 |
C4A—C5A—C6A | 120.78 (7) | C7B—C8B—H8BA | 109.4 |
N2A—C6A—C5A | 112.56 (7) | N3B—C8B—H8BB | 109.4 |
N2A—C6A—H6AA | 109.1 | C7B—C8B—H8BB | 109.4 |
C5A—C6A—H6AA | 109.1 | H8BA—C8B—H8BB | 108.0 |
N2A—C6A—H6AB | 109.1 | N3B—C9B—C10B | 112.76 (7) |
C5A—C6A—H6AB | 109.1 | N3B—C9B—H9BA | 109.0 |
H6AA—C6A—H6AB | 107.8 | C10B—C9B—H9BA | 109.0 |
N2A—C7A—C8A | 111.17 (7) | N3B—C9B—H9BB | 109.0 |
N2A—C7A—H7AA | 109.4 | C10B—C9B—H9BB | 109.0 |
C8A—C7A—H7AA | 109.4 | H9BA—C9B—H9BB | 107.8 |
N2A—C7A—H7AB | 109.4 | N4B—C10B—C11B | 122.01 (8) |
C8A—C7A—H7AB | 109.4 | N4B—C10B—C9B | 118.08 (7) |
H7AA—C7A—H7AB | 108.0 | C11B—C10B—C9B | 119.88 (9) |
N3A—C8A—C7A | 111.08 (7) | C12B—C11B—C10B | 118.89 (10) |
N3A—C8A—H8AA | 109.4 | C12B—C11B—H11B | 120.6 |
C7A—C8A—H8AA | 109.4 | C10B—C11B—H11B | 120.6 |
N3A—C8A—H8AB | 109.4 | C13B—C12B—C11B | 119.03 (8) |
C7A—C8A—H8AB | 109.4 | C13B—C12B—H12B | 120.5 |
H8AA—C8A—H8AB | 108.0 | C11B—C12B—H12B | 120.5 |
N3A—C9A—C10A | 113.01 (7) | C12B—C13B—C14B | 118.73 (9) |
N3A—C9A—H9AA | 109.0 | C12B—C13B—H13B | 120.6 |
C10A—C9A—H9AA | 109.0 | C14B—C13B—H13B | 120.6 |
N3A—C9A—H9AB | 109.0 | N4B—C14B—C13B | 122.44 (9) |
C10A—C9A—H9AB | 109.0 | N4B—C14B—H14B | 118.8 |
H9AA—C9A—H9AB | 107.8 | C13B—C14B—H14B | 118.8 |
N4A—C10A—C11A | 122.03 (8) | N5B—C15B—C16B | 178.72 (10) |
N4A—C10A—C9A | 118.05 (7) | C15B—C16B—H16D | 109.5 |
C11A—C10A—C9A | 119.89 (8) | C15B—C16B—H16E | 109.5 |
C12A—C11A—C10A | 119.04 (9) | H16D—C16B—H16E | 109.5 |
C12A—C11A—H11A | 120.5 | C15B—C16B—H16F | 109.5 |
C10A—C11A—H11A | 120.5 | H16D—C16B—H16F | 109.5 |
C11A—C12A—C13A | 119.00 (8) | H16E—C16B—H16F | 109.5 |
C11A—C12A—H12A | 120.5 | O12—Cl1—O13 | 110.20 (6) |
C13A—C12A—H12A | 120.5 | O12—Cl1—O14 | 110.05 (6) |
C14A—C13A—C12A | 118.56 (8) | O13—Cl1—O14 | 109.68 (7) |
C14A—C13A—H13A | 120.7 | O12—Cl1—O11 | 109.31 (5) |
C12A—C13A—H13A | 120.7 | O13—Cl1—O11 | 108.58 (6) |
N4A—C14A—C13A | 122.55 (9) | O14—Cl1—O11 | 108.98 (5) |
N4A—C14A—H14A | 118.7 | O21—Cl2—O24 | 110.32 (7) |
C13A—C14A—H14A | 118.7 | O21—Cl2—O23 | 109.89 (6) |
N5A—C15A—C16A | 178.76 (10) | O24—Cl2—O23 | 109.62 (7) |
C15A—C16A—H16A | 109.5 | O21—Cl2—O22 | 109.38 (5) |
C15A—C16A—H16B | 109.5 | O24—Cl2—O22 | 108.82 (6) |
H16A—C16A—H16B | 109.5 | O23—Cl2—O22 | 108.78 (5) |
C15A—C16A—H16C | 109.5 | O33—Cl3—O34 | 110.84 (10) |
H16A—C16A—H16C | 109.5 | O33—Cl3—O32 | 110.98 (7) |
H16B—C16A—H16C | 109.5 | O34—Cl3—O32 | 109.27 (9) |
O2W—Zn2—N5B | 86.23 (3) | O33—Cl3—O31 | 108.63 (7) |
O2W—Zn2—N4B | 95.01 (3) | O34—Cl3—O31 | 107.40 (8) |
N5B—Zn2—N4B | 94.02 (3) | O32—Cl3—O31 | 109.64 (6) |
O2W—Zn2—N1B | 94.46 (3) | O44—Cl4—O43 | 109.61 (9) |
N5B—Zn2—N1B | 95.88 (3) | O44—Cl4—O42 | 110.78 (10) |
N4B—Zn2—N1B | 166.72 (3) | O43—Cl4—O42 | 108.45 (8) |
O2W—Zn2—N2B | 173.16 (3) | O44—Cl4—O41 | 110.85 (8) |
N5B—Zn2—N2B | 91.53 (3) | O43—Cl4—O41 | 108.89 (8) |
N4B—Zn2—N2B | 91.59 (3) | O42—Cl4—O41 | 108.19 (7) |
N1B—Zn2—N2B | 79.32 (3) | O41A—Cl4A—O43A | 110.6 (7) |
O2W—Zn2—N3B | 99.39 (3) | O41A—Cl4A—O44A | 110.7 (7) |
N5B—Zn2—N3B | 171.13 (3) | O43A—Cl4A—O44A | 106.2 (8) |
N4B—Zn2—N3B | 78.74 (3) | O41A—Cl4A—O42A | 112.6 (6) |
N1B—Zn2—N3B | 90.55 (3) | O43A—Cl4A—O42A | 107.6 (8) |
N2B—Zn2—N3B | 83.64 (3) | O44A—Cl4A—O42A | 108.9 (7) |
C5A—N1A—C1A—C2A | −0.45 (13) | C5B—N1B—C1B—C2B | 0.17 (13) |
Zn1—N1A—C1A—C2A | −170.73 (7) | Zn2—N1B—C1B—C2B | 171.97 (7) |
N1A—C1A—C2A—C3A | 1.40 (14) | N1B—C1B—C2B—C3B | −0.97 (14) |
C1A—C2A—C3A—C4A | −0.62 (14) | C1B—C2B—C3B—C4B | 0.37 (14) |
C2A—C3A—C4A—C5A | −0.99 (13) | C2B—C3B—C4B—C5B | 0.95 (14) |
C1A—N1A—C5A—C4A | −1.28 (13) | C1B—N1B—C5B—C4B | 1.23 (13) |
Zn1—N1A—C5A—C4A | 170.23 (7) | Zn2—N1B—C5B—C4B | −171.48 (7) |
C1A—N1A—C5A—C6A | 176.98 (8) | C1B—N1B—C5B—C6B | −177.17 (8) |
Zn1—N1A—C5A—C6A | −11.51 (10) | Zn2—N1B—C5B—C6B | 10.12 (10) |
C3A—C4A—C5A—N1A | 2.01 (13) | C3B—C4B—C5B—N1B | −1.80 (14) |
C3A—C4A—C5A—C6A | −176.18 (8) | C3B—C4B—C5B—C6B | 176.53 (9) |
C7A—N2A—C6A—C5A | 88.34 (9) | C7B—N2B—C6B—C5B | −88.80 (9) |
Zn1—N2A—C6A—C5A | −30.44 (8) | Zn2—N2B—C6B—C5B | 29.66 (9) |
N1A—C5A—C6A—N2A | 28.85 (11) | N1B—C5B—C6B—N2B | −27.36 (11) |
C4A—C5A—C6A—N2A | −152.86 (8) | C4B—C5B—C6B—N2B | 154.22 (8) |
C6A—N2A—C7A—C8A | −81.07 (9) | C6B—N2B—C7B—C8B | 80.96 (10) |
Zn1—N2A—C7A—C8A | 39.66 (8) | Zn2—N2B—C7B—C8B | −39.49 (8) |
C9A—N3A—C8A—C7A | −78.77 (9) | C9B—N3B—C8B—C7B | 79.08 (9) |
Zn1—N3A—C8A—C7A | 41.26 (7) | Zn2—N3B—C8B—C7B | −40.87 (8) |
N2A—C7A—C8A—N3A | −57.67 (9) | N2B—C7B—C8B—N3B | 57.50 (10) |
C8A—N3A—C9A—C10A | 95.69 (9) | C8B—N3B—C9B—C10B | −94.37 (9) |
Zn1—N3A—C9A—C10A | −20.81 (9) | Zn2—N3B—C9B—C10B | 21.88 (9) |
C14A—N4A—C10A—C11A | −0.70 (13) | C14B—N4B—C10B—C11B | 0.15 (14) |
Zn1—N4A—C10A—C11A | 173.79 (7) | Zn2—N4B—C10B—C11B | −174.13 (8) |
C14A—N4A—C10A—C9A | 177.04 (8) | C14B—N4B—C10B—C9B | −177.88 (9) |
Zn1—N4A—C10A—C9A | −8.47 (10) | Zn2—N4B—C10B—C9B | 7.84 (11) |
N3A—C9A—C10A—N4A | 20.16 (11) | N3B—C9B—C10B—N4B | −20.49 (12) |
N3A—C9A—C10A—C11A | −162.05 (8) | N3B—C9B—C10B—C11B | 161.43 (9) |
N4A—C10A—C11A—C12A | 1.57 (15) | N4B—C10B—C11B—C12B | −0.97 (16) |
C9A—C10A—C11A—C12A | −176.13 (9) | C9B—C10B—C11B—C12B | 177.03 (10) |
C10A—C11A—C12A—C13A | −0.78 (16) | C10B—C11B—C12B—C13B | 0.76 (17) |
C11A—C12A—C13A—C14A | −0.78 (16) | C11B—C12B—C13B—C14B | 0.20 (17) |
C10A—N4A—C14A—C13A | −0.98 (14) | C10B—N4B—C14B—C13B | 0.88 (15) |
Zn1—N4A—C14A—C13A | −174.93 (7) | Zn2—N4B—C14B—C13B | 174.61 (8) |
C12A—C13A—C14A—N4A | 1.72 (15) | C12B—C13B—C14B—N4B | −1.06 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W2···O41i | 0.80 (1) | 2.04 (1) | 2.8410 (12) | 178 (2) |
O1W—H1W2···O43Ai | 0.80 (1) | 1.94 (2) | 2.730 (15) | 170 (2) |
N2A—H2AB···O41 | 1.00 | 2.28 | 3.1809 (12) | 150 |
N2A—H2AB···O42 | 1.00 | 2.28 | 3.1468 (15) | 144 |
N2A—H2AB···O42A | 1.00 | 2.40 | 3.328 (12) | 153 |
N2A—H2AB···O43A | 1.00 | 2.50 | 3.396 (15) | 149 |
N3A—H3AB···O23 | 1.00 | 2.17 | 3.0889 (12) | 152 |
C4A—H4AA···O42ii | 0.95 | 2.60 | 3.4025 (15) | 142 |
C7A—H7AA···O24iii | 0.99 | 2.41 | 3.1218 (12) | 128 |
C14A—H14A···O32iv | 0.95 | 2.41 | 3.1645 (13) | 136 |
C16A—H16B···O22v | 0.98 | 2.51 | 3.4788 (13) | 169 |
O2W—H2W1···O31iv | 0.82 (1) | 2.00 (1) | 2.8091 (11) | 174 (2) |
O2W—H2W2···O11 | 0.82 (1) | 1.99 (1) | 2.7690 (11) | 159 (2) |
N2B—H2BB···O31vi | 1.00 | 2.36 | 3.2467 (12) | 148 |
N2B—H2BB···O33vi | 1.00 | 2.32 | 3.2331 (15) | 152 |
N3B—H3BB···O14 | 1.00 | 2.20 | 3.1169 (13) | 152 |
C7B—H7BB···O13i | 0.99 | 2.44 | 3.1430 (12) | 128 |
C14B—H14B···O43i | 0.95 | 2.48 | 3.2138 (15) | 134 |
C14B—H14B···O44Ai | 0.95 | 2.32 | 3.149 (13) | 145 |
C16B—H16D···O43Ai | 0.98 | 2.54 | 3.419 (13) | 150 |
C16B—H16E···O11vii | 0.98 | 2.55 | 3.5083 (14) | 166 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) x, y−1, z; (vi) −x, −y+1, −z; (vii) x, y+1, z. |
Acknowledgements
RJB is grateful to Howard University Nanoscience Facility for access to liquid nitrogen.
Funding information
Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (grant No. 1205608, Partnership for Reduced Dimensional Materials, to RJB); NSF MRI program (grant No. CHE-0619278), for the purchase of an X-ray diffractometer.
References
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, K., Costas, M., Kim, J., Tipton, A. K. & Que, L. Jr (2002). J. Am. Chem. Soc. 124, 3026–3035. CrossRef PubMed CAS
Chen, M. S. & White, M. C. (2010). Science, 327, 566–571. CrossRef CAS PubMed
Das, S., Incarvito, C. D., Crabtree, R. H. & Brudvig, G. W. (2006). Science, 312, 1941–1943. CrossRef PubMed CAS
England, J., Britovsek, G. J. P., Rabadia, N. & White, A. J. P. (2007). Inorg. Chem. 46, 3752–3767. CrossRef PubMed CAS
Goodson, P. A., Glerup, J., Hodgson, D. J., Michelsen, K. & Pedersen, E. (1990). Inorg. Chem. 29, 503–508. CSD CrossRef CAS Web of Science
Goodson, P. A., Glerup, J., Hodgson, D. J., Michelsen, K. & Weihe, H. (1991). Inorg. Chem. 30, 4909–4914. CrossRef CAS
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals
Gultneh, Y., Allwar, Ahvazi, B., Blaise, D., Butcher, R. J., Jasinski, J. M. & Jasinski, J. P. (1996). Inorg. Chim. Acta, 241, 31–38. CrossRef CAS
Gultneh, Y., Khan, A. R., Blaise, D., Chaudhry, S., Ahvazi, B., Marvey, B. B. & Butcher, R. J. (1999). J. Inorg. Biochem. 75, 7–18. Web of Science CSD CrossRef CAS
Gunay, A. & Theopold, K. H. (2010). Chem. Rev. 110, 1060–1081. CrossRef CAS PubMed
Hureau, C., Anxolabéhère-Mallart, E., Blondin, G., Rivière, E. & Nierlich, M. (2005a). Eur. J. Inorg. Chem. 23, 4808–4817. CrossRef
Hureau, C., Blondin, G., Charlot, M.-F., Philouze, C., Nierlich, M., Césario, M. & Anxolabéhère-Mallart, E. (2005b). Inorg. Chem. 44, 3669–3683. CrossRef PubMed CAS
Jacobsen, E. N., Zhang, W., Muci, A. R., Ecker, J. R. & Deng, L. (1991). J. Am. Chem. Soc. 113, 7063–7064. CrossRef CAS Web of Science
Mas-Ballesté, R., Costas, R., Van Den Berg, M. T. & Que, L. Jr (2006). Chem. Eur. J. 12, 7489–7500. PubMed
Parajón-Costa, B. S., Echeverría, G. A., Piro, O. E. & Baran, E. J. (2013). Z. Naturforsch. Teil B, 68, 1327–1332.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.