The [2+2] cyclocondensation reaction between sodium 2,6-diformyl-4-chlorophenolate and benzyldiethylenetriamine, using the sodium template method, followed by transmetallation with Zn(CH3COO)2·2H2O, gave an unexpected 18-membered macrocyclic product in which ring contractions have occurred to produce two imidazolidine rings. In the macrocyclic complex, [μ-3,17-dibenzyl-13,27-dichloro-3,6,9,17,20,23-hexaazapentacyclo[23.3.1.111,15.02,6.016,20]triaconta-1(29),9,11(30),12,14,23,25,27-octaene-29,30-diolato]bis[(acetato-κO)zinc(II)] ethanol 1.75-solvate 0.25-hydrate, [Zn2(C38H38Cl2N6O2)(CH3COO)2]·1.75C2H6O·0.25H2O, each of the two ZnII ions has a distorted trigonal bipyramidal environment.
Supporting information
CCDC reference: 189869
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.056
- wR factor = 0.154
- Data-to-parameter ratio = 19.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 36.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
Crystal data top
[Zn2(C38H38Cl2N6O2)(C2H3O2)2]·1.75C2H6O·0.25H2O | F(000) = 2112 |
Mr = 1015.60 | Dx = 1.407 Mg m−3 |
Monoclinic, P21/c | Melting point = 488–497 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 26.0725 (4) Å | Cell parameters from 8192 reflections |
b = 9.5836 (1) Å | θ = 2.4–28.3° |
c = 19.7483 (1) Å | µ = 1.17 mm−1 |
β = 103.658 (1)° | T = 293 K |
V = 4794.94 (9) Å3 | Slab, pale yellow |
Z = 4 | 0.54 × 0.44 × 0.26 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 11428 independent reflections |
Radiation source: fine-focus sealed tube | 7553 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.093 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.2°, θmin = 2.4° |
ω scans | h = −30→34 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −12→12 |
Tmin = 0.571, Tmax = 0.751 | l = −23→26 |
28105 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.154 | w = 1/[σ2(Fo2) + (0.0609P)2P] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.001 |
11428 reflections | Δρmax = 0.81 e Å−3 |
584 parameters | Δρmin = −1.04 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0035 (4) |
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. |
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 (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.269754 (15) | 0.64198 (4) | 0.63759 (2) | 0.02491 (12) | |
Zn2 | 0.220378 (15) | 0.49683 (4) | 0.74888 (2) | 0.02565 (12) | |
Cl1 | 0.43154 (5) | 0.95767 (14) | 0.94726 (5) | 0.0577 (3) | |
Cl2 | 0.00810 (4) | 0.97639 (10) | 0.61455 (6) | 0.0442 (3) | |
O1 | 0.28967 (9) | 0.5965 (3) | 0.74306 (11) | 0.0266 (5) | |
O2 | 0.19385 (8) | 0.6056 (2) | 0.65590 (12) | 0.0256 (5) | |
O3 | 0.25569 (16) | 0.2921 (3) | 0.83281 (15) | 0.0719 (11) | |
O4 | 0.23253 (10) | 0.3046 (3) | 0.71954 (12) | 0.0315 (6) | |
O5 | 0.27729 (11) | 0.4591 (3) | 0.59440 (12) | 0.0358 (6) | |
O6 | 0.26397 (10) | 0.6081 (3) | 0.50650 (13) | 0.0393 (7) | |
N1 | 0.43859 (11) | 0.7024 (4) | 0.71021 (15) | 0.0346 (7) | |
N2 | 0.34949 (11) | 0.7331 (3) | 0.64832 (14) | 0.0310 (7) | |
N3 | 0.24682 (11) | 0.8416 (3) | 0.61205 (15) | 0.0266 (6) | |
N4 | 0.05061 (11) | 0.4419 (3) | 0.68676 (16) | 0.0293 (7) | |
N5 | 0.13676 (11) | 0.4641 (3) | 0.75359 (15) | 0.0281 (7) | |
N6 | 0.22313 (11) | 0.5982 (3) | 0.84016 (14) | 0.0253 (6) | |
C1 | 0.32072 (13) | 0.6771 (3) | 0.79093 (16) | 0.0237 (7) | |
C2 | 0.30674 (13) | 0.7210 (4) | 0.85286 (16) | 0.0248 (7) | |
C3 | 0.34118 (14) | 0.8112 (4) | 0.89969 (18) | 0.0298 (8) | |
H3 | 0.3317 | 0.8434 | 0.9395 | 0.036* | |
C4 | 0.38821 (15) | 0.8507 (4) | 0.88656 (18) | 0.0327 (8) | |
C5 | 0.40291 (14) | 0.8101 (4) | 0.82616 (17) | 0.0306 (8) | |
H5 | 0.4344 | 0.8412 | 0.8172 | 0.037* | |
C6 | 0.36944 (13) | 0.7217 (4) | 0.77924 (17) | 0.0290 (8) | |
C7 | 0.38400 (13) | 0.6708 (4) | 0.71311 (18) | 0.0302 (8) | |
H7 | 0.3794 | 0.5693 | 0.7106 | 0.036* | |
C8 | 0.43851 (15) | 0.7155 (6) | 0.6355 (2) | 0.0587 (14) | |
H8A | 0.4606 | 0.6443 | 0.6219 | 0.070* | |
H8B | 0.4514 | 0.8065 | 0.6258 | 0.070* | |
C9 | 0.38060 (14) | 0.6963 (5) | 0.59631 (19) | 0.0379 (9) | |
H9A | 0.3717 | 0.7577 | 0.5562 | 0.046* | |
H9B | 0.3739 | 0.6007 | 0.5807 | 0.046* | |
C10 | 0.34117 (13) | 0.8876 (4) | 0.65021 (19) | 0.0321 (8) | |
H10A | 0.3708 | 0.9362 | 0.6393 | 0.039* | |
H10B | 0.3385 | 0.9157 | 0.6964 | 0.039* | |
C11 | 0.29031 (13) | 0.9249 (4) | 0.59675 (19) | 0.0318 (8) | |
H11A | 0.2828 | 1.0236 | 0.5995 | 0.038* | |
H11B | 0.2941 | 0.9046 | 0.5501 | 0.038* | |
C12 | 0.20139 (13) | 0.8983 (4) | 0.60717 (18) | 0.0276 (8) | |
H12 | 0.1978 | 0.9911 | 0.5930 | 0.033* | |
C13 | 0.15476 (13) | 0.8310 (3) | 0.62173 (17) | 0.0242 (7) | |
C14 | 0.10942 (13) | 0.9175 (4) | 0.61197 (19) | 0.0298 (8) | |
H14 | 0.1106 | 1.0083 | 0.5958 | 0.036* | |
C15 | 0.06350 (13) | 0.8667 (4) | 0.62659 (19) | 0.0305 (8) | |
C16 | 0.06105 (13) | 0.7313 (4) | 0.65114 (18) | 0.0298 (8) | |
H16 | 0.0301 | 0.6989 | 0.6615 | 0.036* | |
C17 | 0.10467 (13) | 0.6449 (4) | 0.66015 (18) | 0.0259 (7) | |
C18 | 0.15265 (12) | 0.6912 (3) | 0.64623 (17) | 0.0228 (7) | |
C19 | 0.10319 (13) | 0.4926 (4) | 0.68297 (18) | 0.0276 (8) | |
H19 | 0.1158 | 0.4341 | 0.6495 | 0.033* | |
C20 | 0.05957 (15) | 0.3213 (4) | 0.7349 (2) | 0.0380 (9) | |
H20A | 0.0483 | 0.2352 | 0.7099 | 0.046* | |
H20B | 0.0405 | 0.3326 | 0.7711 | 0.046* | |
C21 | 0.11922 (14) | 0.3207 (4) | 0.7658 (2) | 0.0333 (8) | |
H21A | 0.1271 | 0.2997 | 0.8152 | 0.040* | |
H21B | 0.1365 | 0.2521 | 0.7426 | 0.040* | |
C22 | 0.12853 (14) | 0.5616 (4) | 0.80982 (19) | 0.0321 (8) | |
H22A | 0.0983 | 0.5318 | 0.8268 | 0.039* | |
H22B | 0.1219 | 0.6554 | 0.7913 | 0.039* | |
C23 | 0.17813 (14) | 0.5603 (4) | 0.86940 (18) | 0.0313 (8) | |
H23A | 0.1746 | 0.6267 | 0.9051 | 0.038* | |
H23B | 0.1834 | 0.4682 | 0.8903 | 0.038* | |
C24 | 0.25936 (13) | 0.6796 (3) | 0.87459 (17) | 0.0244 (7) | |
H24 | 0.2549 | 0.7148 | 0.9167 | 0.029* | |
C25 | 0.47594 (15) | 0.5982 (5) | 0.7488 (2) | 0.0433 (10) | |
H25A | 0.4755 | 0.5164 | 0.7197 | 0.052* | |
H25B | 0.4646 | 0.5698 | 0.7900 | 0.052* | |
C26 | 0.53133 (14) | 0.6539 (4) | 0.7701 (2) | 0.0363 (9) | |
C27 | 0.55077 (17) | 0.7032 (5) | 0.8372 (2) | 0.0542 (12) | |
H27 | 0.5302 | 0.6990 | 0.8698 | 0.065* | |
C28 | 0.6026 (2) | 0.7603 (6) | 0.8557 (3) | 0.0718 (17) | |
H28 | 0.6155 | 0.7949 | 0.9005 | 0.086* | |
C29 | 0.63340 (18) | 0.7652 (5) | 0.8092 (3) | 0.0667 (15) | |
H29 | 0.6670 | 0.8039 | 0.8218 | 0.080* | |
C30 | 0.61471 (17) | 0.7131 (6) | 0.7438 (3) | 0.0620 (14) | |
H30 | 0.6359 | 0.7144 | 0.7120 | 0.074* | |
C31 | 0.56461 (16) | 0.6585 (5) | 0.7248 (2) | 0.0484 (11) | |
H31 | 0.5526 | 0.6234 | 0.6799 | 0.058* | |
C32 | 0.01579 (14) | 0.4119 (4) | 0.61823 (19) | 0.0348 (9) | |
H32A | 0.0251 | 0.3217 | 0.6023 | 0.042* | |
H32B | 0.0215 | 0.4816 | 0.5852 | 0.042* | |
C33 | −0.04195 (14) | 0.4110 (4) | 0.61919 (19) | 0.0308 (8) | |
C34 | −0.06017 (15) | 0.4573 (4) | 0.6760 (2) | 0.0336 (8) | |
H34 | −0.0360 | 0.4863 | 0.7160 | 0.040* | |
C35 | −0.11364 (16) | 0.4611 (4) | 0.6742 (2) | 0.0413 (10) | |
H35 | −0.1250 | 0.4908 | 0.7131 | 0.050* | |
C36 | −0.15037 (16) | 0.4204 (4) | 0.6142 (2) | 0.0427 (10) | |
H36 | −0.1863 | 0.4255 | 0.6124 | 0.051* | |
C37 | −0.13310 (16) | 0.3722 (4) | 0.5571 (2) | 0.0442 (10) | |
H37 | −0.1575 | 0.3450 | 0.5169 | 0.053* | |
C38 | −0.07955 (16) | 0.3649 (4) | 0.5602 (2) | 0.0394 (9) | |
H38 | −0.0683 | 0.3286 | 0.5225 | 0.047* | |
C39 | 0.24767 (15) | 0.2326 (4) | 0.77573 (19) | 0.0331 (8) | |
C40 | 0.27346 (13) | 0.4890 (4) | 0.53037 (18) | 0.0309 (8) | |
C41 | 0.2818 (2) | 0.3710 (5) | 0.4837 (2) | 0.0560 (13) | |
H41A | 0.2559 | 0.3762 | 0.4403 | 0.084* | |
H41B | 0.2785 | 0.2835 | 0.5060 | 0.084* | |
H41C | 0.3165 | 0.3780 | 0.4751 | 0.084* | |
C42 | 0.25493 (19) | 0.0796 (4) | 0.7699 (2) | 0.0486 (11) | |
H42A | 0.2725 | 0.0428 | 0.8146 | 0.073* | |
H42B | 0.2759 | 0.0615 | 0.7369 | 0.073* | |
H42C | 0.2211 | 0.0356 | 0.7545 | 0.073* | |
O7 | 0.16291 (14) | 0.2267 (3) | 0.59201 (17) | 0.0675 (10) | |
H7A | 0.1841 | 0.2685 | 0.6225 | 0.101* | |
C43 | 0.1521 (2) | 0.3067 (6) | 0.5301 (2) | 0.0693 (16) | |
H43A | 0.1832 | 0.3103 | 0.5112 | 0.083* | |
H43B | 0.1431 | 0.4014 | 0.5402 | 0.083* | |
C44 | 0.1076 (2) | 0.2431 (7) | 0.4782 (2) | 0.0749 (17) | |
H44A | 0.1004 | 0.2975 | 0.4362 | 0.112* | |
H44B | 0.0768 | 0.2409 | 0.4969 | 0.112* | |
H44C | 0.1168 | 0.1497 | 0.4681 | 0.112* | |
O8 | 0.3354 (2) | 0.0652 (5) | 0.4492 (3) | 0.0775 (15) | 0.75 |
H8 | 0.3078 | 0.0937 | 0.4241 | 0.116* | 0.75 |
C45 | 0.3726 (5) | 0.1048 (9) | 0.4263 (6) | 0.101 (3) | 0.75 |
H45A | 0.3785 | 0.2035 | 0.4359 | 0.121* | 0.75 |
H45B | 0.3643 | 0.0920 | 0.3762 | 0.121* | 0.75 |
C46 | 0.4174 (6) | 0.0323 (19) | 0.4558 (11) | 0.240 (11) | 0.75 |
H46A | 0.4460 | 0.0651 | 0.4371 | 0.360* | 0.75 |
H46B | 0.4117 | −0.0652 | 0.4457 | 0.360* | 0.75 |
H46C | 0.4259 | 0.0462 | 0.5053 | 0.360* | 0.75 |
O1W | 0.4633 (8) | 0.187 (2) | 0.4667 (9) | 0.109 (6)* | 0.25 |
H1W | 0.4510 | 0.2729 | 0.4528 | 0.164* | 0.25 |
H2W | 0.4979 | 0.1747 | 0.4856 | 0.164* | 0.25 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0222 (2) | 0.0288 (2) | 0.0230 (2) | 0.00032 (16) | 0.00388 (15) | −0.00475 (17) |
Zn2 | 0.0262 (2) | 0.0259 (2) | 0.0241 (2) | −0.00037 (16) | 0.00447 (16) | −0.00391 (16) |
Cl1 | 0.0590 (7) | 0.0791 (9) | 0.0325 (6) | −0.0376 (6) | 0.0060 (5) | −0.0206 (5) |
Cl2 | 0.0279 (5) | 0.0369 (6) | 0.0684 (7) | 0.0092 (4) | 0.0125 (5) | 0.0064 (5) |
O1 | 0.0274 (13) | 0.0342 (14) | 0.0181 (11) | −0.0042 (10) | 0.0051 (9) | −0.0067 (10) |
O2 | 0.0208 (12) | 0.0237 (13) | 0.0311 (13) | 0.0037 (9) | 0.0040 (10) | 0.0029 (10) |
O3 | 0.134 (3) | 0.042 (2) | 0.0328 (17) | 0.026 (2) | 0.0062 (19) | 0.0013 (15) |
O4 | 0.0369 (14) | 0.0250 (13) | 0.0317 (14) | 0.0013 (11) | 0.0061 (11) | 0.0007 (11) |
O5 | 0.0510 (17) | 0.0322 (15) | 0.0244 (13) | 0.0036 (12) | 0.0093 (12) | −0.0029 (11) |
O6 | 0.0423 (16) | 0.0459 (18) | 0.0288 (14) | 0.0033 (13) | 0.0067 (12) | 0.0076 (12) |
N1 | 0.0203 (15) | 0.050 (2) | 0.0322 (17) | −0.0002 (14) | 0.0037 (13) | −0.0041 (15) |
N2 | 0.0206 (15) | 0.052 (2) | 0.0193 (14) | −0.0002 (13) | 0.0034 (11) | −0.0074 (14) |
N3 | 0.0255 (15) | 0.0259 (16) | 0.0280 (15) | −0.0036 (12) | 0.0058 (12) | 0.0012 (12) |
N4 | 0.0245 (15) | 0.0254 (16) | 0.0367 (17) | −0.0059 (12) | 0.0049 (13) | 0.0032 (13) |
N5 | 0.0284 (15) | 0.0215 (15) | 0.0332 (17) | −0.0046 (12) | 0.0050 (13) | 0.0022 (12) |
N6 | 0.0277 (15) | 0.0273 (16) | 0.0214 (14) | −0.0017 (12) | 0.0069 (12) | −0.0006 (12) |
C1 | 0.0257 (17) | 0.0244 (18) | 0.0185 (16) | 0.0024 (13) | 0.0002 (13) | −0.0027 (13) |
C2 | 0.0261 (17) | 0.0305 (19) | 0.0158 (16) | 0.0002 (14) | 0.0011 (13) | −0.0004 (14) |
C3 | 0.039 (2) | 0.0275 (19) | 0.0205 (17) | −0.0038 (15) | 0.0034 (15) | −0.0036 (14) |
C4 | 0.037 (2) | 0.036 (2) | 0.0216 (17) | −0.0080 (16) | −0.0003 (15) | −0.0054 (15) |
C5 | 0.0246 (18) | 0.038 (2) | 0.0252 (18) | −0.0052 (15) | −0.0023 (14) | −0.0003 (16) |
C6 | 0.0235 (17) | 0.040 (2) | 0.0214 (17) | 0.0009 (15) | 0.0005 (14) | −0.0022 (15) |
C7 | 0.0232 (17) | 0.037 (2) | 0.0287 (19) | −0.0015 (15) | 0.0033 (14) | −0.0030 (16) |
C8 | 0.025 (2) | 0.118 (5) | 0.032 (2) | 0.001 (2) | 0.0055 (17) | −0.006 (3) |
C9 | 0.0233 (18) | 0.060 (3) | 0.032 (2) | −0.0015 (17) | 0.0104 (16) | −0.0092 (19) |
C10 | 0.0255 (18) | 0.042 (2) | 0.0294 (19) | −0.0073 (15) | 0.0068 (15) | −0.0026 (16) |
C11 | 0.0276 (19) | 0.035 (2) | 0.033 (2) | −0.0062 (15) | 0.0088 (15) | 0.0057 (16) |
C12 | 0.0288 (18) | 0.0210 (18) | 0.0310 (19) | −0.0035 (14) | 0.0035 (15) | 0.0029 (14) |
C13 | 0.0214 (16) | 0.0225 (18) | 0.0285 (18) | 0.0008 (13) | 0.0055 (14) | 0.0051 (14) |
C14 | 0.0297 (19) | 0.0200 (18) | 0.038 (2) | 0.0013 (14) | 0.0052 (16) | 0.0043 (15) |
C15 | 0.0229 (17) | 0.030 (2) | 0.039 (2) | 0.0037 (14) | 0.0070 (15) | −0.0008 (16) |
C16 | 0.0216 (17) | 0.037 (2) | 0.0298 (19) | −0.0028 (14) | 0.0047 (14) | 0.0001 (16) |
C17 | 0.0240 (17) | 0.0249 (18) | 0.0278 (18) | −0.0038 (13) | 0.0040 (14) | 0.0013 (14) |
C18 | 0.0229 (16) | 0.0193 (17) | 0.0248 (17) | −0.0002 (12) | 0.0025 (13) | −0.0007 (13) |
C19 | 0.0216 (17) | 0.0295 (19) | 0.0314 (19) | −0.0042 (14) | 0.0057 (14) | 0.0019 (15) |
C20 | 0.035 (2) | 0.027 (2) | 0.052 (2) | −0.0072 (16) | 0.0113 (18) | 0.0070 (18) |
C21 | 0.034 (2) | 0.0198 (18) | 0.046 (2) | −0.0052 (14) | 0.0095 (17) | 0.0051 (16) |
C22 | 0.0292 (19) | 0.031 (2) | 0.038 (2) | 0.0003 (15) | 0.0129 (16) | 0.0008 (17) |
C23 | 0.036 (2) | 0.033 (2) | 0.0272 (19) | −0.0024 (16) | 0.0124 (16) | 0.0003 (16) |
C24 | 0.0328 (19) | 0.0226 (18) | 0.0179 (16) | 0.0025 (14) | 0.0063 (14) | −0.0004 (13) |
C25 | 0.032 (2) | 0.042 (2) | 0.053 (3) | 0.0011 (17) | 0.0053 (19) | −0.005 (2) |
C26 | 0.0258 (19) | 0.033 (2) | 0.046 (2) | 0.0033 (15) | 0.0008 (17) | −0.0019 (18) |
C27 | 0.040 (3) | 0.064 (3) | 0.052 (3) | 0.010 (2) | 0.000 (2) | −0.010 (2) |
C28 | 0.048 (3) | 0.074 (4) | 0.072 (4) | 0.010 (3) | −0.028 (3) | −0.029 (3) |
C29 | 0.030 (2) | 0.050 (3) | 0.112 (5) | −0.004 (2) | 0.000 (3) | 0.003 (3) |
C30 | 0.029 (2) | 0.075 (4) | 0.081 (4) | 0.004 (2) | 0.011 (2) | 0.022 (3) |
C31 | 0.031 (2) | 0.059 (3) | 0.053 (3) | 0.0118 (19) | 0.0065 (19) | 0.004 (2) |
C32 | 0.034 (2) | 0.034 (2) | 0.035 (2) | −0.0081 (16) | 0.0067 (16) | −0.0080 (17) |
C33 | 0.033 (2) | 0.0239 (19) | 0.034 (2) | −0.0069 (15) | 0.0048 (16) | 0.0042 (16) |
C34 | 0.031 (2) | 0.032 (2) | 0.035 (2) | −0.0039 (15) | 0.0011 (16) | −0.0024 (16) |
C35 | 0.039 (2) | 0.037 (2) | 0.050 (3) | 0.0023 (17) | 0.013 (2) | 0.0035 (19) |
C36 | 0.030 (2) | 0.034 (2) | 0.062 (3) | −0.0030 (17) | 0.0051 (19) | 0.011 (2) |
C37 | 0.036 (2) | 0.044 (3) | 0.044 (2) | −0.0074 (18) | −0.0057 (19) | 0.010 (2) |
C38 | 0.041 (2) | 0.043 (2) | 0.031 (2) | −0.0075 (18) | 0.0038 (17) | 0.0023 (18) |
C39 | 0.035 (2) | 0.033 (2) | 0.031 (2) | 0.0065 (16) | 0.0076 (16) | 0.0019 (16) |
C40 | 0.0219 (18) | 0.046 (2) | 0.0231 (18) | −0.0013 (15) | 0.0007 (14) | −0.0005 (16) |
C41 | 0.075 (3) | 0.062 (3) | 0.033 (2) | 0.009 (3) | 0.016 (2) | −0.012 (2) |
C42 | 0.064 (3) | 0.028 (2) | 0.055 (3) | 0.010 (2) | 0.016 (2) | 0.001 (2) |
O7 | 0.086 (3) | 0.0416 (19) | 0.056 (2) | −0.0086 (17) | −0.0204 (18) | 0.0025 (16) |
C43 | 0.095 (4) | 0.060 (3) | 0.048 (3) | −0.032 (3) | 0.009 (3) | 0.001 (3) |
C44 | 0.087 (4) | 0.089 (4) | 0.040 (3) | −0.014 (3) | −0.003 (3) | 0.000 (3) |
O8 | 0.112 (5) | 0.040 (3) | 0.084 (4) | 0.011 (3) | 0.031 (3) | −0.012 (3) |
C45 | 0.147 (10) | 0.056 (5) | 0.119 (8) | −0.049 (6) | 0.070 (8) | −0.017 (5) |
C46 | 0.129 (13) | 0.225 (19) | 0.36 (3) | −0.078 (12) | 0.037 (15) | −0.195 (18) |
Geometric parameters (Å, º) top
Zn1—O5 | 1.979 (3) | C17—C19 | 1.531 (5) |
Zn1—N3 | 2.032 (3) | C19—H19 | 0.98 |
Zn1—O1 | 2.071 (2) | C20—C21 | 1.531 (5) |
Zn1—O2 | 2.123 (2) | C20—H20A | 0.97 |
Zn1—N2 | 2.219 (3) | C20—H20B | 0.97 |
Zn1—C40 | 2.596 (4) | C21—H21A | 0.97 |
Zn1—Zn2 | 3.1238 (6) | C21—H21B | 0.97 |
Zn2—O4 | 1.979 (2) | C22—C23 | 1.529 (5) |
Zn2—N6 | 2.034 (3) | C22—H22A | 0.97 |
Zn2—O1 | 2.070 (2) | C22—H22B | 0.97 |
Zn2—O2 | 2.083 (2) | C23—H23A | 0.97 |
Zn2—N5 | 2.226 (3) | C23—H23B | 0.97 |
Cl1—C4 | 1.768 (4) | C24—H24 | 0.93 |
Cl2—C15 | 1.756 (4) | C25—C26 | 1.504 (5) |
O1—C1 | 1.336 (4) | C25—H25A | 0.97 |
O2—C18 | 1.329 (4) | C25—H25B | 0.97 |
O3—C39 | 1.236 (4) | C26—C27 | 1.386 (6) |
O4—C39 | 1.287 (4) | C26—C31 | 1.387 (6) |
O5—C40 | 1.277 (4) | C27—C28 | 1.423 (7) |
O6—C40 | 1.237 (4) | C27—H27 | 0.93 |
N1—C7 | 1.469 (4) | C28—C29 | 1.356 (8) |
N1—C25 | 1.475 (5) | C28—H28 | 0.93 |
N1—C8 | 1.481 (5) | C29—C30 | 1.364 (7) |
N2—C9 | 1.493 (4) | C29—H29 | 0.93 |
N2—C10 | 1.498 (5) | C30—C31 | 1.374 (6) |
N2—C7 | 1.503 (4) | C30—H30 | 0.93 |
N3—C12 | 1.286 (4) | C31—H31 | 0.93 |
N3—C11 | 1.475 (4) | C32—C33 | 1.510 (5) |
N4—C32 | 1.469 (4) | C32—H32A | 0.97 |
N4—C19 | 1.473 (4) | C32—H32B | 0.97 |
N4—C20 | 1.480 (5) | C33—C34 | 1.390 (5) |
N5—C21 | 1.486 (4) | C33—C38 | 1.405 (5) |
N5—C19 | 1.486 (4) | C34—C35 | 1.387 (5) |
N5—C22 | 1.505 (5) | C34—H34 | 0.93 |
N6—C24 | 1.288 (4) | C35—C36 | 1.392 (6) |
N6—C23 | 1.471 (4) | C35—H35 | 0.93 |
C1—C6 | 1.410 (5) | C36—C37 | 1.388 (6) |
C1—C2 | 1.420 (4) | C36—H36 | 0.93 |
C2—C3 | 1.420 (5) | C37—C38 | 1.385 (6) |
C2—C24 | 1.455 (5) | C37—H37 | 0.93 |
C3—C4 | 1.366 (5) | C38—H38 | 0.93 |
C3—H3 | 0.93 | C39—C42 | 1.486 (5) |
C4—C5 | 1.392 (5) | C40—C41 | 1.507 (5) |
C5—C6 | 1.399 (5) | C41—H41A | 0.96 |
C5—H5 | 0.93 | C41—H41B | 0.96 |
C6—C7 | 1.524 (5) | C41—H41C | 0.96 |
C7—H7 | 0.98 | C42—H42A | 0.96 |
C8—C9 | 1.536 (5) | C42—H42B | 0.96 |
C8—H8A | 0.97 | C42—H42C | 0.96 |
C8—H8B | 0.97 | O7—C43 | 1.414 (5) |
C9—H9A | 0.97 | O7—H7A | 0.82 |
C9—H9B | 0.97 | C43—C44 | 1.485 (6) |
C10—C11 | 1.530 (5) | C43—H43A | 0.97 |
C10—H10A | 0.97 | C43—H43B | 0.97 |
C10—H10B | 0.97 | C44—H44A | 0.96 |
C11—H11A | 0.97 | C44—H44B | 0.96 |
C11—H11B | 0.97 | C44—H44C | 0.96 |
C12—C13 | 1.464 (4) | O8—C45 | 1.222 (10) |
C12—H12 | 0.93 | O8—H8 | 0.82 |
C13—C14 | 1.419 (5) | C45—C46 | 1.365 (19) |
C13—C18 | 1.430 (5) | C45—H45A | 0.97 |
C14—C15 | 1.385 (5) | C45—H45B | 0.97 |
C14—H14 | 0.93 | C46—H46A | 0.96 |
C15—C16 | 1.393 (5) | C46—H46B | 0.96 |
C16—C17 | 1.384 (5) | C46—H46C | 0.96 |
C16—H16 | 0.93 | O1W—H1W | 0.90 |
C17—C18 | 1.414 (4) | O1W—H2W | 0.90 |
| | | |
O5—Zn1—N3 | 141.26 (11) | C18—C17—C19 | 116.2 (3) |
O5—Zn1—O1 | 102.72 (10) | O2—C18—C17 | 120.0 (3) |
N3—Zn1—O1 | 115.93 (10) | O2—C18—C13 | 122.2 (3) |
O5—Zn1—O2 | 96.87 (10) | C17—C18—C13 | 117.8 (3) |
N3—Zn1—O2 | 88.01 (10) | N4—C19—N5 | 103.9 (3) |
O1—Zn1—O2 | 79.43 (9) | N4—C19—C17 | 114.7 (3) |
O5—Zn1—N2 | 101.75 (11) | N5—C19—C17 | 113.6 (3) |
N3—Zn1—N2 | 82.36 (12) | N4—C19—H19 | 108.1 |
O1—Zn1—N2 | 88.87 (9) | N5—C19—H19 | 108.1 |
O2—Zn1—N2 | 159.82 (10) | C17—C19—H19 | 108.1 |
O5—Zn1—C40 | 28.57 (11) | N4—C20—C21 | 104.5 (3) |
N3—Zn1—C40 | 113.23 (12) | N4—C20—H20A | 110.8 |
O1—Zn1—C40 | 130.76 (11) | C21—C20—H20A | 110.8 |
O2—Zn1—C40 | 105.20 (10) | N4—C20—H20B | 110.8 |
N2—Zn1—C40 | 94.91 (11) | C21—C20—H20B | 110.8 |
O5—Zn1—Zn2 | 90.47 (8) | H20A—C20—H20B | 108.9 |
N3—Zn1—Zn2 | 116.61 (8) | N5—C21—C20 | 104.8 (3) |
O1—Zn1—Zn2 | 41.03 (6) | N5—C21—H21A | 110.8 |
O2—Zn1—Zn2 | 41.54 (6) | C20—C21—H21A | 110.8 |
N2—Zn1—Zn2 | 129.85 (7) | N5—C21—H21B | 110.8 |
C40—Zn1—Zn2 | 115.05 (9) | C20—C21—H21B | 110.8 |
O4—Zn2—N6 | 136.85 (11) | H21A—C21—H21B | 108.9 |
O4—Zn2—O1 | 102.18 (10) | N5—C22—C23 | 108.7 (3) |
N6—Zn2—O1 | 88.87 (10) | N5—C22—H22A | 110.0 |
O4—Zn2—O2 | 104.52 (10) | C23—C22—H22A | 110.0 |
N6—Zn2—O2 | 118.48 (11) | N5—C22—H22B | 110.0 |
O1—Zn2—O2 | 80.36 (9) | C23—C22—H22B | 110.0 |
O4—Zn2—N5 | 96.15 (10) | H22A—C22—H22B | 108.3 |
N6—Zn2—N5 | 81.96 (11) | N6—C23—C22 | 107.7 (3) |
O1—Zn2—N5 | 160.60 (10) | N6—C23—H23A | 110.2 |
O2—Zn2—N5 | 89.01 (10) | C22—C23—H23A | 110.2 |
O4—Zn2—Zn1 | 95.02 (7) | N6—C23—H23B | 110.2 |
N6—Zn2—Zn1 | 118.46 (8) | C22—C23—H23B | 110.2 |
O1—Zn2—Zn1 | 41.03 (6) | H23A—C23—H23B | 108.5 |
O2—Zn2—Zn1 | 42.52 (6) | N6—C24—C2 | 125.2 (3) |
N5—Zn2—Zn1 | 131.49 (8) | N6—C24—H24 | 117.4 |
C1—O1—Zn2 | 128.2 (2) | C2—C24—H24 | 117.4 |
C1—O1—Zn1 | 123.8 (2) | N1—C25—C26 | 112.2 (3) |
Zn2—O1—Zn1 | 97.94 (9) | N1—C25—H25A | 109.2 |
C18—O2—Zn2 | 121.6 (2) | C26—C25—H25A | 109.2 |
C18—O2—Zn1 | 129.0 (2) | N1—C25—H25B | 109.2 |
Zn2—O2—Zn1 | 95.94 (9) | C26—C25—H25B | 109.2 |
C39—O4—Zn2 | 106.5 (2) | H25A—C25—H25B | 107.9 |
C40—O5—Zn1 | 103.6 (2) | C27—C26—C31 | 117.6 (4) |
C7—N1—C25 | 111.6 (3) | C27—C26—C25 | 120.0 (4) |
C7—N1—C8 | 106.4 (3) | C31—C26—C25 | 122.4 (4) |
C25—N1—C8 | 114.7 (3) | C26—C27—C28 | 119.2 (5) |
C9—N2—C10 | 110.8 (3) | C26—C27—H27 | 120.4 |
C9—N2—C7 | 100.3 (3) | C28—C27—H27 | 120.4 |
C10—N2—C7 | 115.6 (3) | C29—C28—C27 | 121.2 (5) |
C9—N2—Zn1 | 119.4 (2) | C29—C28—H28 | 119.4 |
C10—N2—Zn1 | 104.7 (2) | C27—C28—H28 | 119.4 |
C7—N2—Zn1 | 106.5 (2) | C28—C29—C30 | 119.5 (4) |
C12—N3—C11 | 119.7 (3) | C28—C29—H29 | 120.3 |
C12—N3—Zn1 | 128.9 (2) | C30—C29—H29 | 120.3 |
C11—N3—Zn1 | 111.4 (2) | C29—C30—C31 | 120.2 (5) |
C32—N4—C19 | 113.4 (3) | C29—C30—H30 | 119.9 |
C32—N4—C20 | 114.1 (3) | C31—C30—H30 | 119.9 |
C19—N4—C20 | 106.4 (3) | C30—C31—C26 | 122.3 (5) |
C21—N5—C19 | 100.7 (3) | C30—C31—H31 | 118.8 |
C21—N5—C22 | 110.6 (3) | C26—C31—H31 | 118.8 |
C19—N5—C22 | 115.0 (3) | N4—C32—C33 | 113.0 (3) |
C21—N5—Zn2 | 118.6 (2) | N4—C32—H32A | 109.0 |
C19—N5—Zn2 | 107.5 (2) | C33—C32—H32A | 109.0 |
C22—N5—Zn2 | 104.8 (2) | N4—C32—H32B | 109.0 |
C24—N6—C23 | 119.7 (3) | C33—C32—H32B | 109.0 |
C24—N6—Zn2 | 128.7 (2) | H32A—C32—H32B | 107.8 |
C23—N6—Zn2 | 111.4 (2) | C34—C33—C38 | 117.7 (3) |
O1—C1—C6 | 118.6 (3) | C34—C33—C32 | 122.7 (3) |
O1—C1—C2 | 123.0 (3) | C38—C33—C32 | 119.6 (3) |
C6—C1—C2 | 118.4 (3) | C35—C34—C33 | 121.4 (4) |
C1—C2—C3 | 119.3 (3) | C35—C34—H34 | 119.3 |
C1—C2—C24 | 125.6 (3) | C33—C34—H34 | 119.3 |
C3—C2—C24 | 115.1 (3) | C34—C35—C36 | 119.9 (4) |
C4—C3—C2 | 120.2 (3) | C34—C35—H35 | 120.0 |
C4—C3—H3 | 119.9 | C36—C35—H35 | 120.0 |
C2—C3—H3 | 119.9 | C37—C36—C35 | 119.7 (4) |
C3—C4—C5 | 121.8 (3) | C37—C36—H36 | 120.2 |
C3—C4—Cl1 | 119.4 (3) | C35—C36—H36 | 120.2 |
C5—C4—Cl1 | 118.8 (3) | C38—C37—C36 | 119.9 (4) |
C4—C5—C6 | 118.8 (3) | C38—C37—H37 | 120.1 |
C4—C5—H5 | 120.6 | C36—C37—H37 | 120.1 |
C6—C5—H5 | 120.6 | C37—C38—C33 | 121.3 (4) |
C5—C6—C1 | 121.4 (3) | C37—C38—H38 | 119.3 |
C5—C6—C7 | 121.3 (3) | C33—C38—H38 | 119.3 |
C1—C6—C7 | 117.4 (3) | O3—C39—O4 | 119.3 (3) |
N1—C7—N2 | 106.0 (3) | O3—C39—C42 | 121.9 (4) |
N1—C7—C6 | 114.0 (3) | O4—C39—C42 | 118.8 (3) |
N2—C7—C6 | 112.5 (3) | O6—C40—O5 | 123.1 (4) |
N1—C7—H7 | 108.0 | O6—C40—C41 | 120.3 (3) |
N2—C7—H7 | 108.0 | O5—C40—C41 | 116.6 (4) |
C6—C7—H7 | 108.0 | O6—C40—Zn1 | 75.4 (2) |
N1—C8—C9 | 105.2 (3) | C41—C40—Zn1 | 164.0 (3) |
N1—C8—H8A | 110.7 | C40—C41—H41A | 109.5 |
C9—C8—H8A | 110.7 | C40—C41—H41B | 109.5 |
N1—C8—H8B | 110.7 | H41A—C41—H41B | 109.5 |
C9—C8—H8B | 110.7 | C40—C41—H41C | 109.5 |
H8A—C8—H8B | 108.8 | H41A—C41—H41C | 109.5 |
N2—C9—C8 | 104.7 (3) | H41B—C41—H41C | 109.5 |
N2—C9—H9A | 110.8 | C39—C42—H42A | 109.5 |
C8—C9—H9A | 110.8 | C39—C42—H42B | 109.5 |
N2—C9—H9B | 110.8 | H42A—C42—H42B | 109.5 |
C8—C9—H9B | 110.8 | C39—C42—H42C | 109.5 |
H9A—C9—H9B | 108.9 | H42A—C42—H42C | 109.5 |
N2—C10—C11 | 108.7 (3) | H42B—C42—H42C | 109.5 |
N2—C10—H10A | 109.9 | C43—O7—H7A | 109.5 |
C11—C10—H10A | 109.9 | O7—C43—C44 | 109.7 (4) |
N2—C10—H10B | 109.9 | O7—C43—H43A | 109.7 |
C11—C10—H10B | 109.9 | C44—C43—H43A | 109.7 |
H10A—C10—H10B | 108.3 | O7—C43—H43B | 109.7 |
N3—C11—C10 | 108.4 (3) | C44—C43—H43B | 109.7 |
N3—C11—H11A | 110.0 | H43A—C43—H43B | 108.2 |
C10—C11—H11A | 110.0 | C43—C44—H44A | 109.5 |
N3—C11—H11B | 110.0 | C43—C44—H44B | 109.5 |
C10—C11—H11B | 110.0 | H44A—C44—H44B | 109.5 |
H11A—C11—H11B | 108.4 | C43—C44—H44C | 109.5 |
N3—C12—C13 | 126.3 (3) | H44A—C44—H44C | 109.5 |
N3—C12—H12 | 116.8 | H44B—C44—H44C | 109.5 |
C13—C12—H12 | 116.8 | C45—O8—H8 | 109.5 |
C14—C13—C18 | 119.7 (3) | O8—C45—C46 | 110.9 (11) |
C14—C13—C12 | 114.8 (3) | O8—C45—H45A | 109.5 |
C18—C13—C12 | 125.4 (3) | C46—C45—H45A | 109.5 |
C15—C14—C13 | 120.0 (3) | O8—C45—H45B | 109.5 |
C15—C14—H14 | 120.0 | C46—C45—H45B | 109.5 |
C13—C14—H14 | 120.0 | H45A—C45—H45B | 108.0 |
C14—C15—C16 | 120.9 (3) | C45—C46—H46A | 109.5 |
C14—C15—Cl2 | 119.0 (3) | C45—C46—H46B | 109.5 |
C16—C15—Cl2 | 120.1 (3) | H46A—C46—H46B | 109.5 |
C17—C16—C15 | 119.9 (3) | C45—C46—H46C | 109.5 |
C17—C16—H16 | 120.0 | H46A—C46—H46C | 109.5 |
C15—C16—H16 | 120.0 | H46B—C46—H46C | 109.5 |
C16—C17—C18 | 121.7 (3) | H1W—O1W—H2W | 120.0 |
C16—C17—C19 | 122.1 (3) | | |
| | | |
O5—Zn1—Zn2—O4 | 6.22 (10) | O1—C1—C2—C24 | 3.5 (5) |
N3—Zn1—Zn2—O4 | 157.45 (11) | C6—C1—C2—C24 | −177.0 (3) |
O1—Zn1—Zn2—O4 | −102.81 (12) | C1—C2—C3—C4 | −2.5 (5) |
O2—Zn1—Zn2—O4 | 106.06 (12) | C24—C2—C3—C4 | 176.5 (3) |
N2—Zn1—Zn2—O4 | −99.57 (13) | C2—C3—C4—C5 | 3.0 (6) |
C40—Zn1—Zn2—O4 | 21.30 (11) | C2—C3—C4—Cl1 | −177.6 (3) |
O5—Zn1—Zn2—N6 | 157.94 (12) | C3—C4—C5—C6 | −2.7 (6) |
N3—Zn1—Zn2—N6 | −50.83 (13) | Cl1—C4—C5—C6 | 177.9 (3) |
O1—Zn1—Zn2—N6 | 48.92 (14) | C4—C5—C6—C1 | 2.1 (5) |
O2—Zn1—Zn2—N6 | −102.21 (13) | C4—C5—C6—C7 | −178.5 (3) |
N2—Zn1—Zn2—N6 | 52.15 (14) | O1—C1—C6—C5 | 177.8 (3) |
C40—Zn1—Zn2—N6 | 173.02 (12) | C2—C1—C6—C5 | −1.7 (5) |
O5—Zn1—Zn2—O1 | 109.02 (13) | O1—C1—C6—C7 | −1.7 (5) |
N3—Zn1—Zn2—O1 | −99.74 (13) | C2—C1—C6—C7 | 178.8 (3) |
O2—Zn1—Zn2—O1 | −151.13 (14) | C25—N1—C7—N2 | −153.0 (3) |
N2—Zn1—Zn2—O1 | 3.23 (15) | C8—N1—C7—N2 | −27.2 (4) |
C40—Zn1—Zn2—O1 | 124.10 (13) | C25—N1—C7—C6 | 82.7 (4) |
O5—Zn1—Zn2—O2 | −99.85 (12) | C8—N1—C7—C6 | −151.5 (4) |
N3—Zn1—Zn2—O2 | 51.39 (13) | C9—N2—C7—N1 | 40.8 (4) |
O1—Zn1—Zn2—O2 | 151.13 (14) | C10—N2—C7—N1 | −78.4 (3) |
N2—Zn1—Zn2—O2 | 154.36 (14) | Zn1—N2—C7—N1 | 165.8 (2) |
C40—Zn1—Zn2—O2 | −84.77 (13) | C9—N2—C7—C6 | 166.1 (3) |
O5—Zn1—Zn2—N5 | −96.57 (13) | C10—N2—C7—C6 | 46.8 (4) |
N3—Zn1—Zn2—N5 | 54.66 (14) | Zn1—N2—C7—C6 | −69.0 (3) |
O1—Zn1—Zn2—N5 | 154.41 (14) | C5—C6—C7—N1 | 10.0 (5) |
O2—Zn1—Zn2—N5 | 3.28 (13) | C1—C6—C7—N1 | −170.5 (3) |
N2—Zn1—Zn2—N5 | 157.64 (15) | C5—C6—C7—N2 | −110.7 (4) |
C40—Zn1—Zn2—N5 | −81.49 (13) | C1—C6—C7—N2 | 68.8 (4) |
O4—Zn2—O1—C1 | −130.9 (3) | C7—N1—C8—C9 | 2.5 (5) |
N6—Zn2—O1—C1 | 7.0 (3) | C25—N1—C8—C9 | 126.4 (4) |
O2—Zn2—O1—C1 | 126.2 (3) | C10—N2—C9—C8 | 84.3 (4) |
N5—Zn2—O1—C1 | 68.5 (4) | C7—N2—C9—C8 | −38.4 (4) |
Zn1—Zn2—O1—C1 | 145.5 (3) | Zn1—N2—C9—C8 | −154.0 (3) |
O4—Zn2—O1—Zn1 | 83.59 (11) | N1—C8—C9—N2 | 23.1 (5) |
N6—Zn2—O1—Zn1 | −138.49 (11) | C9—N2—C10—C11 | 89.3 (3) |
O2—Zn2—O1—Zn1 | −19.33 (9) | C7—N2—C10—C11 | −157.4 (3) |
N5—Zn2—O1—Zn1 | −77.0 (3) | Zn1—N2—C10—C11 | −40.6 (3) |
O5—Zn1—O1—C1 | 136.6 (2) | C12—N3—C11—C10 | 139.6 (3) |
N3—Zn1—O1—C1 | −46.1 (3) | Zn1—N3—C11—C10 | −41.4 (3) |
O2—Zn1—O1—C1 | −128.6 (3) | N2—C10—C11—N3 | 55.6 (4) |
N2—Zn1—O1—C1 | 34.9 (3) | C11—N3—C12—C13 | −178.8 (3) |
C40—Zn1—O1—C1 | 130.4 (2) | Zn1—N3—C12—C13 | 2.3 (5) |
Zn2—Zn1—O1—C1 | −147.6 (3) | N3—C12—C13—C14 | −179.8 (3) |
O5—Zn1—O1—Zn2 | −75.73 (12) | N3—C12—C13—C18 | 2.3 (6) |
N3—Zn1—O1—Zn2 | 101.54 (12) | C18—C13—C14—C15 | 0.4 (5) |
O2—Zn1—O1—Zn2 | 19.01 (9) | C12—C13—C14—C15 | −177.6 (3) |
N2—Zn1—O1—Zn2 | −177.52 (11) | C13—C14—C15—C16 | 0.2 (6) |
C40—Zn1—O1—Zn2 | −82.01 (14) | C13—C14—C15—Cl2 | 179.6 (3) |
O4—Zn2—O2—C18 | 134.8 (2) | C14—C15—C16—C17 | −1.0 (5) |
N6—Zn2—O2—C18 | −41.6 (3) | Cl2—C15—C16—C17 | 179.6 (3) |
O1—Zn2—O2—C18 | −125.0 (2) | C15—C16—C17—C18 | 1.2 (5) |
N5—Zn2—O2—C18 | 38.7 (2) | C15—C16—C17—C19 | −176.4 (3) |
Zn1—Zn2—O2—C18 | −143.8 (3) | Zn2—O2—C18—C17 | −50.8 (4) |
O4—Zn2—O2—Zn1 | −81.44 (10) | Zn1—O2—C18—C17 | 178.4 (2) |
N6—Zn2—O2—Zn1 | 102.15 (11) | Zn2—O2—C18—C13 | 129.3 (3) |
O1—Zn2—O2—Zn1 | 18.75 (9) | Zn1—O2—C18—C13 | −1.5 (4) |
N5—Zn2—O2—Zn1 | −177.55 (10) | C16—C17—C18—O2 | 179.6 (3) |
O5—Zn1—O2—C18 | −137.4 (3) | C19—C17—C18—O2 | −2.7 (5) |
N3—Zn1—O2—C18 | 4.0 (3) | C16—C17—C18—C13 | −0.5 (5) |
O1—Zn1—O2—C18 | 120.9 (3) | C19—C17—C18—C13 | 177.2 (3) |
N2—Zn1—O2—C18 | 65.3 (4) | C14—C13—C18—O2 | 179.6 (3) |
C40—Zn1—O2—C18 | −109.5 (3) | C12—C13—C18—O2 | −2.5 (5) |
Zn2—Zn1—O2—C18 | 139.7 (3) | C14—C13—C18—C17 | −0.3 (5) |
O5—Zn1—O2—Zn2 | 82.91 (10) | C12—C13—C18—C17 | 177.6 (3) |
N3—Zn1—O2—Zn2 | −135.65 (11) | C32—N4—C19—N5 | −159.0 (3) |
O1—Zn1—O2—Zn2 | −18.81 (9) | C20—N4—C19—N5 | −32.8 (4) |
N2—Zn1—O2—Zn2 | −74.3 (3) | C32—N4—C19—C17 | 76.3 (4) |
C40—Zn1—O2—Zn2 | 110.80 (11) | C20—N4—C19—C17 | −157.5 (3) |
N6—Zn2—O4—C39 | −2.9 (3) | C21—N5—C19—N4 | 44.2 (3) |
O1—Zn2—O4—C39 | 98.7 (2) | C22—N5—C19—N4 | −74.7 (3) |
O2—Zn2—O4—C39 | −178.3 (2) | Zn2—N5—C19—N4 | 169.0 (2) |
N5—Zn2—O4—C39 | −87.7 (2) | C21—N5—C19—C17 | 169.5 (3) |
Zn1—Zn2—O4—C39 | 139.6 (2) | C22—N5—C19—C17 | 50.6 (4) |
N3—Zn1—O5—C40 | 13.9 (3) | Zn2—N5—C19—C17 | −65.7 (3) |
O1—Zn1—O5—C40 | −170.0 (2) | C16—C17—C19—N4 | 6.5 (5) |
O2—Zn1—O5—C40 | 109.3 (2) | C18—C17—C19—N4 | −171.2 (3) |
N2—Zn1—O5—C40 | −78.5 (2) | C16—C17—C19—N5 | −112.9 (4) |
Zn2—Zn1—O5—C40 | 150.5 (2) | C18—C17—C19—N5 | 69.4 (4) |
O5—Zn1—N2—C9 | 31.1 (3) | C32—N4—C20—C21 | 133.9 (3) |
N3—Zn1—N2—C9 | −109.8 (3) | C19—N4—C20—C21 | 8.1 (4) |
O1—Zn1—N2—C9 | 133.9 (3) | C19—N5—C21—C20 | −38.8 (4) |
O2—Zn1—N2—C9 | −172.0 (3) | C22—N5—C21—C20 | 83.3 (4) |
C40—Zn1—N2—C9 | 3.0 (3) | Zn2—N5—C21—C20 | −155.7 (2) |
Zn2—Zn1—N2—C9 | 131.7 (2) | N4—C20—C21—N5 | 19.4 (4) |
O5—Zn1—N2—C10 | 155.8 (2) | C21—N5—C22—C23 | 89.5 (3) |
N3—Zn1—N2—C10 | 14.9 (2) | C19—N5—C22—C23 | −157.3 (3) |
O1—Zn1—N2—C10 | −101.4 (2) | Zn2—N5—C22—C23 | −39.5 (3) |
O2—Zn1—N2—C10 | −47.3 (4) | C24—N6—C23—C22 | 139.8 (3) |
C40—Zn1—N2—C10 | 127.8 (2) | Zn2—N6—C23—C22 | −44.2 (3) |
Zn2—Zn1—N2—C10 | −103.5 (2) | N5—C22—C23—N6 | 56.4 (4) |
O5—Zn1—N2—C7 | −81.2 (2) | C23—N6—C24—C2 | 177.6 (3) |
N3—Zn1—N2—C7 | 137.9 (2) | Zn2—N6—C24—C2 | 2.4 (5) |
O1—Zn1—N2—C7 | 21.5 (2) | C1—C2—C24—N6 | −0.7 (6) |
O2—Zn1—N2—C7 | 75.7 (4) | C3—C2—C24—N6 | −179.7 (3) |
C40—Zn1—N2—C7 | −109.3 (2) | C7—N1—C25—C26 | −158.0 (3) |
Zn2—Zn1—N2—C7 | 19.4 (3) | C8—N1—C25—C26 | 80.9 (4) |
O5—Zn1—N3—C12 | 94.2 (3) | N1—C25—C26—C27 | 98.8 (5) |
O1—Zn1—N3—C12 | −81.6 (3) | N1—C25—C26—C31 | −81.2 (5) |
O2—Zn1—N3—C12 | −4.3 (3) | C31—C26—C27—C28 | 2.3 (6) |
N2—Zn1—N3—C12 | −166.6 (3) | C25—C26—C27—C28 | −177.7 (4) |
C40—Zn1—N3—C12 | 101.4 (3) | C26—C27—C28—C29 | −1.0 (8) |
Zn2—Zn1—N3—C12 | −35.6 (3) | C27—C28—C29—C30 | −0.8 (8) |
O5—Zn1—N3—C11 | −84.8 (3) | C28—C29—C30—C31 | 1.3 (8) |
O1—Zn1—N3—C11 | 99.5 (2) | C29—C30—C31—C26 | 0.0 (7) |
O2—Zn1—N3—C11 | 176.7 (2) | C27—C26—C31—C30 | −1.8 (6) |
N2—Zn1—N3—C11 | 14.5 (2) | C25—C26—C31—C30 | 178.1 (4) |
C40—Zn1—N3—C11 | −77.6 (2) | C19—N4—C32—C33 | −159.3 (3) |
Zn2—Zn1—N3—C11 | 145.50 (19) | C20—N4—C32—C33 | 78.7 (4) |
O4—Zn2—N5—C21 | 25.4 (3) | N4—C32—C33—C34 | 10.4 (5) |
N6—Zn2—N5—C21 | −111.1 (3) | N4—C32—C33—C38 | −171.1 (3) |
O1—Zn2—N5—C21 | −173.6 (3) | C38—C33—C34—C35 | −1.5 (6) |
O2—Zn2—N5—C21 | 129.9 (3) | C32—C33—C34—C35 | 177.1 (4) |
Zn1—Zn2—N5—C21 | 127.7 (2) | C33—C34—C35—C36 | −1.2 (6) |
O4—Zn2—N5—C19 | −87.8 (2) | C34—C35—C36—C37 | 1.9 (6) |
N6—Zn2—N5—C19 | 135.7 (2) | C35—C36—C37—C38 | 0.1 (6) |
O1—Zn2—N5—C19 | 73.1 (4) | C36—C37—C38—C33 | −2.8 (6) |
O2—Zn2—N5—C19 | 16.7 (2) | C34—C33—C38—C37 | 3.5 (6) |
Zn1—Zn2—N5—C19 | 14.5 (2) | C32—C33—C38—C37 | −175.1 (4) |
O4—Zn2—N5—C22 | 149.4 (2) | Zn2—O4—C39—O3 | −5.7 (4) |
N6—Zn2—N5—C22 | 12.8 (2) | Zn2—O4—C39—C42 | 174.2 (3) |
O1—Zn2—N5—C22 | −49.7 (4) | Zn1—O5—C40—O6 | −3.8 (4) |
O2—Zn2—N5—C22 | −106.1 (2) | Zn1—O5—C40—C41 | 175.5 (3) |
Zn1—Zn2—N5—C22 | −108.3 (2) | O5—Zn1—C40—O6 | 176.7 (4) |
O4—Zn2—N6—C24 | 102.3 (3) | N3—Zn1—C40—O6 | 6.2 (2) |
O1—Zn2—N6—C24 | −4.4 (3) | O1—Zn1—C40—O6 | −170.37 (18) |
O2—Zn2—N6—C24 | −82.8 (3) | O2—Zn1—C40—O6 | 100.6 (2) |
N5—Zn2—N6—C24 | −167.2 (3) | N2—Zn1—C40—O6 | −77.6 (2) |
Zn1—Zn2—N6—C24 | −34.0 (3) | Zn2—Zn1—C40—O6 | 143.78 (18) |
O4—Zn2—N6—C23 | −73.2 (3) | N3—Zn1—C40—O5 | −170.6 (2) |
O1—Zn2—N6—C23 | −179.9 (2) | O1—Zn1—C40—O5 | 12.9 (3) |
O2—Zn2—N6—C23 | 101.7 (2) | O2—Zn1—C40—O5 | −76.1 (2) |
N5—Zn2—N6—C23 | 17.3 (2) | N2—Zn1—C40—O5 | 105.6 (2) |
Zn1—Zn2—N6—C23 | 150.4 (2) | Zn2—Zn1—C40—O5 | −33.0 (2) |
Zn2—O1—C1—C6 | 172.8 (2) | O5—Zn1—C40—C41 | −14.8 (10) |
Zn1—O1—C1—C6 | −49.6 (4) | N3—Zn1—C40—C41 | 174.6 (10) |
Zn2—O1—C1—C2 | −7.7 (5) | O1—Zn1—C40—C41 | −1.9 (11) |
Zn1—O1—C1—C2 | 129.9 (3) | O2—Zn1—C40—C41 | −90.9 (11) |
O1—C1—C2—C3 | −177.6 (3) | N2—Zn1—C40—C41 | 90.8 (11) |
C6—C1—C2—C3 | 1.9 (5) | Zn2—Zn1—C40—C41 | −47.8 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O4 | 0.82 | 2.07 | 2.835 (4) | 158 |
C3—H3···O6i | 0.93 | 2.49 | 3.332 (4) | 151 |
C12—H12···O7ii | 0.93 | 2.43 | 3.295 (5) | 154 |
C14—H14···O7ii | 0.93 | 2.51 | 3.338 (5) | 149 |
C24—H24···O6i | 0.93 | 2.43 | 3.285 (4) | 154 |
C29—H29···O5iii | 0.93 | 2.43 | 3.226 (6) | 143 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y+1, z; (iii) −x+1, y+1/2, −z+3/2. |