metal-organic compounds
The hydroxide group in the centrosymmetric title complex, {[Zn4(C9H6O5)3(OH)2(C10H8N2)2]·2H2O}n, which adopts a three-dimensional network structure, bridges three Zn atoms. One of the symmetry-independent dicarboxylate groups chelates to a Zn—OH—Zn unit through the carboxyl group on the aromatic ring, while its other oxyacetate arm uses only one O atom for binding. The other dicarboxylate dianion is disordered over a center of inversion and functions as a chelating ligand to two Zn—OH—Zn units. The modes of coordination by the hydroxide, heterocycle and dicarboxylate ligands give rise to tetrahedral coordination for one Zn atom and octahedral coordination for the other.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020859/ci6423sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020859/ci6423Isup2.hkl |
CCDC reference: 251620
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
polymeric tris(µ3-4-carboxyphenoxyacetato)di-µ3-hydroxo-bis(µ2-4,4'-
pyridine)tetrazinc(IV) dihydrate top
Crystal data top
[Zn4(C9H6O5)3(OH)2(C10H8N2)2]·2H2O | Z = 1 |
Mr = 1226.31 | F(000) = 622 |
Triclinic, P1 | Dx = 1.682 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.679 (4) Å | Cell parameters from 12424 reflections |
b = 10.913 (4) Å | θ = 3.3–27.5° |
c = 12.140 (4) Å | µ = 2.04 mm−1 |
α = 112.43 (3)° | T = 295 K |
β = 104.07 (3)° | Prism, colourless |
γ = 100.10 (3)° | 0.39 × 0.27 × 0.18 mm |
V = 1210.4 (8) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5503 independent reflections |
Radiation source: fine-focus sealed tube | 4737 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→12 |
Tmin = 0.545, Tmax = 0.696 | k = −14→14 |
11901 measured reflections | l = −14→15 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0515P)2 + 3.5764P] where P = (Fo2 + 2Fc2)/3 |
5503 reflections | (Δ/σ)max = 0.001 |
370 parameters | Δρmax = 0.94 e Å−3 |
271 restraints | Δρmin = −0.95 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.48181 (4) | 0.42010 (5) | 0.85313 (4) | 0.0228 (1) | |
Zn2 | 0.76061 (4) | 0.42965 (5) | 1.01609 (4) | 0.0248 (1) | |
O1 | 0.5643 (3) | 0.2776 (3) | 0.7418 (3) | 0.0371 (7) | |
O2 | 0.7537 (3) | 0.2723 (4) | 0.8656 (3) | 0.0401 (8) | |
O3 | 0.8481 (3) | 0.0142 (3) | 0.3466 (3) | 0.0406 (8) | |
O4 | 0.5605 (4) | −0.1598 (3) | 0.0645 (3) | 0.0424 (8) | |
O5 | 0.6712 (3) | −0.2460 (3) | 0.1837 (3) | 0.0325 (6) | |
O6 | 0.6465 (3) | 0.5822 (3) | 0.8749 (3) | 0.0341 (7) | |
O7 | 0.8424 (3) | 0.5964 (3) | 1.0053 (3) | 0.0368 (7) | |
O8 | 1.043 (1) | 1.159 (1) | 0.987 (1) | 0.039 (3) | 0.50 |
O9 | 0.5858 (2) | 0.4284 (3) | 1.0310 (2) | 0.0212 (5) | |
O1w | 0.504 (1) | −0.101 (1) | −0.1443 (9) | 0.187 (4) | |
N1 | 0.3629 (3) | 0.4199 (3) | 0.6833 (3) | 0.0298 (7) | |
N2 | −0.1038 (3) | 0.4260 (3) | 0.1627 (3) | 0.0276 (7) | |
C1 | 0.364 (1) | 0.5380 (9) | 0.675 (1) | 0.032 (2) | 0.50 |
C2 | 0.2780 (8) | 0.543 (1) | 0.5718 (8) | 0.039 (2) | 0.50 |
C3 | 0.1849 (4) | 0.4209 (4) | 0.4727 (4) | 0.0325 (9) | |
C4 | 0.189 (1) | 0.299 (1) | 0.4833 (12) | 0.046 (3) | 0.50 |
C5 | 0.2766 (8) | 0.301 (1) | 0.5888 (9) | 0.053 (3) | 0.50 |
C6 | 0.0262 (7) | 0.5006 (8) | 0.206 (1) | 0.036 (2) | 0.50 |
C7 | 0.125 (1) | 0.5023 (9) | 0.306 (1) | 0.041 (2) | 0.50 |
C8 | 0.0864 (4) | 0.4219 (4) | 0.3640 (4) | 0.0303 (9) | |
C9 | −0.048 (1) | 0.345 (1) | 0.319 (1) | 0.044 (3) | 0.50 |
C10 | −0.140 (1) | 0.3491 (9) | 0.219 (1) | 0.044 (2) | 0.50 |
C1' | 0.393 (1) | 0.5177 (8) | 0.6458 (9) | 0.032 (2) | 0.50 |
C2' | 0.3082 (8) | 0.523 (1) | 0.5421 (8) | 0.039 (2) | 0.50 |
C4' | 0.150 (1) | 0.318 (1) | 0.510 (1) | 0.046 (3) | 0.50 |
C5' | 0.2422 (7) | 0.323 (1) | 0.615 (1) | 0.053 (3) | 0.50 |
C6' | 0.0085 (7) | 0.532 (1) | 0.2340 (9) | 0.036 (2) | 0.50 |
C7' | 0.104 (1) | 0.532 (1) | 0.334 (1) | 0.041 (2) | 0.50 |
C9' | −0.030 (1) | 0.312 (1) | 0.288 (1) | 0.044 (3) | 0.50 |
C10' | −0.122 (1) | 0.318 (1) | 0.189 (1) | 0.044 (2) | 0.50 |
C11 | 0.6698 (4) | 0.2431 (4) | 0.7582 (4) | 0.0283 (8) | |
C12 | 0.7053 (3) | 0.1649 (3) | 0.6448 (2) | 0.0283 (8) | |
C13 | 0.8298 (3) | 0.1389 (3) | 0.6621 (2) | 0.038 (1) | |
C14 | 0.8727 (2) | 0.0849 (3) | 0.5591 (2) | 0.040 (1) | |
C15 | 0.7911 (3) | 0.0569 (3) | 0.4388 (2) | 0.0314 (9) | |
C16 | 0.6667 (2) | 0.0829 (3) | 0.4215 (2) | 0.0339 (9) | |
C17 | 0.6238 (2) | 0.1369 (3) | 0.5245 (2) | 0.0324 (9) | |
C18 | 0.7701 (5) | −0.0153 (5) | 0.2212 (4) | 0.037 (1) | |
C19 | 0.6563 (4) | −0.1527 (4) | 0.1513 (4) | 0.0277 (8) | |
C20 | 0.7688 (4) | 0.6399 (4) | 0.9396 (4) | 0.0257 (8) | |
C21 | 0.847 (1) | 0.7737 (9) | 0.9462 (10) | 0.024 (4) | 0.50 |
C22 | 0.984 (1) | 0.831 (1) | 1.0150 (12) | 0.030 (4) | 0.50 |
C23 | 1.0533 (6) | 0.960 (1) | 1.029 (1) | 0.029 (3) | 0.50 |
C24 | 0.9847 (6) | 1.0309 (9) | 0.9748 (13) | 0.030 (3) | 0.50 |
C25 | 0.7780 (6) | 0.8448 (7) | 0.8916 (7) | 0.034 (2) | 0.50 |
C26 | 0.8470 (7) | 0.9734 (7) | 0.9059 (8) | 0.039 (2) | 0.50 |
C27 | 1.181 (2) | 1.228 (1) | 1.069 (2) | 0.028 (3) | 0.50 |
H9o | 0.5458 | 0.3401 | 1.0305 | 0.025* | |
H1w1 | 0.5236 | −0.1155 | −0.0763 | 0.224* | |
H1w2 | 0.4877 | −0.0202 | −0.1165 | 0.224* | |
H1 | 0.4249 | 0.6205 | 0.7411 | 0.039* | 0.50 |
H2 | 0.2826 | 0.6270 | 0.5688 | 0.047* | 0.50 |
H4 | 0.1305 | 0.2150 | 0.4179 | 0.056* | 0.50 |
H5 | 0.2756 | 0.2174 | 0.5938 | 0.063* | 0.50 |
H6 | 0.0522 | 0.5546 | 0.1676 | 0.043* | 0.50 |
H7 | 0.2140 | 0.5560 | 0.3332 | 0.049* | 0.50 |
H9 | −0.0771 | 0.2901 | 0.3562 | 0.053* | 0.50 |
H10 | −0.2298 | 0.2964 | 0.1903 | 0.053* | 0.50 |
H1' | 0.4764 | 0.5864 | 0.6915 | 0.039* | 0.50 |
H2' | 0.3337 | 0.5933 | 0.5197 | 0.047* | 0.50 |
H4' | 0.0670 | 0.2488 | 0.4661 | 0.056* | 0.50 |
H5' | 0.2189 | 0.2539 | 0.6401 | 0.063* | 0.50 |
H6' | 0.0230 | 0.6076 | 0.2163 | 0.043* | 0.50 |
H7' | 0.1823 | 0.6068 | 0.3809 | 0.049* | 0.50 |
H9' | −0.0461 | 0.2338 | 0.3026 | 0.053* | 0.50 |
H10' | −0.1996 | 0.2428 | 0.1393 | 0.053* | 0.50 |
H13 | 0.8843 | 0.1577 | 0.7426 | 0.045* | |
H14 | 0.9559 | 0.0676 | 0.5707 | 0.048* | |
H16 | 0.6121 | 0.0641 | 0.3410 | 0.041* | |
H17 | 0.5405 | 0.1542 | 0.5130 | 0.039* | |
H18a | 0.8301 | −0.0168 | 0.1725 | 0.044* | |
H18b | 0.7311 | 0.0595 | 0.2252 | 0.044* | |
H22 | 1.0303 | 0.7838 | 1.0515 | 0.037* | 0.50 |
H23 | 1.1454 | 0.9984 | 1.0754 | 0.035* | 0.50 |
H26 | 0.8011 | 1.0209 | 0.8694 | 0.047* | 0.50 |
H25 | 0.6859 | 0.8062 | 0.8455 | 0.040* | 0.50 |
H27a | 1.2361 | 1.1683 | 1.0439 | 0.033* | 0.50 |
H27b | 1.1872 | 1.2488 | 1.1551 | 0.033* | 0.50 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0213 (2) | 0.0263 (2) | 0.0188 (2) | 0.0074 (2) | 0.0024 (2) | 0.0106 (2) |
Zn2 | 0.0216 (2) | 0.0304 (3) | 0.0227 (2) | 0.0086 (2) | 0.0033 (2) | 0.0145 (2) |
O1 | 0.037 (2) | 0.043 (2) | 0.028 (2) | 0.020 (1) | 0.010 (1) | 0.010 (1) |
O2 | 0.044 (2) | 0.049 (2) | 0.024 (2) | 0.026 (2) | 0.008 (1) | 0.010 (1) |
O3 | 0.033 (2) | 0.041 (2) | 0.030 (2) | 0.004 (1) | 0.012 (1) | 0.000 (1) |
O4 | 0.049 (2) | 0.031 (2) | 0.044 (2) | 0.006 (1) | 0.005 (2) | 0.023 (2) |
O5 | 0.031 (2) | 0.028 (2) | 0.034 (2) | 0.003 (1) | 0.004 (1) | 0.015 (1) |
O6 | 0.026 (2) | 0.034 (2) | 0.036 (2) | −0.004 (1) | 0.003 (1) | 0.020 (1) |
O7 | 0.028 (2) | 0.041 (2) | 0.048 (2) | 0.009 (1) | 0.009 (1) | 0.030 (2) |
O8 | 0.025 (4) | 0.034 (5) | 0.061 (6) | 0.002 (4) | 0.006 (4) | 0.032 (5) |
O9 | 0.019 (1) | 0.021 (1) | 0.022 (1) | 0.005 (1) | 0.004 (1) | 0.010 (1) |
O1w | 0.284 (9) | 0.172 (7) | 0.142 (6) | 0.133 (6) | 0.049 (5) | 0.095 (5) |
N1 | 0.031 (2) | 0.029 (2) | 0.022 (2) | 0.007 (1) | −0.002 (1) | 0.012 (1) |
N2 | 0.024 (2) | 0.034 (2) | 0.023 (2) | 0.008 (1) | 0.002 (1) | 0.015 (1) |
C1 | 0.026 (4) | 0.037 (3) | 0.028 (4) | 0.001 (2) | 0.001 (3) | 0.017 (3) |
C2 | 0.035 (4) | 0.042 (3) | 0.038 (4) | 0.001 (3) | 0.000 (3) | 0.027 (3) |
C3 | 0.032 (2) | 0.031 (2) | 0.027 (2) | 0.004 (2) | −0.003 (2) | 0.017 (2) |
C4 | 0.042 (5) | 0.040 (3) | 0.040 (4) | −0.003 (3) | −0.013 (3) | 0.023 (3) |
C5 | 0.056 (5) | 0.042 (4) | 0.047 (4) | 0.004 (3) | −0.012 (3) | 0.029 (3) |
C6 | 0.041 (3) | 0.024 (4) | 0.033 (4) | 0.007 (3) | −0.001 (3) | 0.015 (3) |
C7 | 0.038 (4) | 0.036 (4) | 0.039 (4) | 0.000 (3) | −0.006 (3) | 0.022 (4) |
C8 | 0.030 (2) | 0.029 (2) | 0.025 (2) | 0.004 (2) | −0.002 (2) | 0.014 (2) |
C9 | 0.042 (3) | 0.034 (5) | 0.047 (5) | −0.001 (3) | −0.006 (3) | 0.027 (4) |
C10 | 0.034 (3) | 0.041 (4) | 0.046 (5) | −0.002 (3) | −0.008 (3) | 0.026 (4) |
C1' | 0.026 (4) | 0.037 (3) | 0.028 (4) | 0.001 (2) | 0.001 (3) | 0.017 (3) |
C2' | 0.035 (4) | 0.042 (3) | 0.038 (4) | 0.001 (3) | 0.000 (3) | 0.027 (3) |
C4' | 0.042 (5) | 0.040 (3) | 0.040 (4) | −0.003 (3) | −0.013 (3) | 0.023 (3) |
C5' | 0.056 (5) | 0.042 (4) | 0.047 (4) | 0.004 (3) | −0.012 (3) | 0.029 (3) |
C6' | 0.041 (3) | 0.024 (4) | 0.033 (4) | 0.007 (3) | −0.001 (3) | 0.015 (3) |
C7' | 0.038 (4) | 0.036 (4) | 0.039 (4) | 0.000 (3) | −0.006 (3) | 0.022 (4) |
C9' | 0.042 (3) | 0.034 (5) | 0.047 (5) | −0.001 (3) | −0.006 (3) | 0.027 (4) |
C10' | 0.034 (3) | 0.041 (4) | 0.046 (5) | −0.002 (3) | −0.008 (3) | 0.026 (4) |
C11 | 0.032 (2) | 0.024 (2) | 0.027 (2) | 0.008 (2) | 0.008 (2) | 0.010 (2) |
C12 | 0.031 (2) | 0.027 (2) | 0.026 (2) | 0.010 (2) | 0.011 (2) | 0.010 (2) |
C13 | 0.041 (2) | 0.043 (3) | 0.029 (2) | 0.020 (2) | 0.010 (2) | 0.014 (2) |
C14 | 0.033 (2) | 0.048 (3) | 0.035 (2) | 0.021 (2) | 0.009 (2) | 0.011 (2) |
C15 | 0.035 (2) | 0.024 (2) | 0.028 (2) | 0.006 (2) | 0.015 (2) | 0.003 (2) |
C16 | 0.032 (2) | 0.035 (2) | 0.024 (2) | 0.005 (2) | 0.005 (2) | 0.008 (2) |
C17 | 0.028 (2) | 0.031 (2) | 0.030 (2) | 0.007 (2) | 0.006 (2) | 0.009 (2) |
C18 | 0.041 (2) | 0.029 (2) | 0.032 (2) | −0.001 (2) | 0.015 (2) | 0.009 (2) |
C19 | 0.030 (2) | 0.025 (2) | 0.025 (2) | 0.005 (2) | 0.012 (2) | 0.008 (2) |
C20 | 0.026 (2) | 0.025 (2) | 0.026 (2) | 0.005 (2) | 0.010 (2) | 0.013 (2) |
C21 | 0.019 (7) | 0.023 (5) | 0.027 (6) | 0.005 (4) | 0.007 (5) | 0.011 (4) |
C22 | 0.022 (6) | 0.030 (6) | 0.036 (6) | 0.004 (4) | 0.007 (4) | 0.015 (4) |
C23 | 0.019 (5) | 0.031 (5) | 0.038 (5) | 0.004 (4) | 0.011 (4) | 0.017 (4) |
C24 | 0.019 (5) | 0.026 (5) | 0.041 (5) | 0.000 (4) | 0.010 (4) | 0.015 (4) |
C26 | 0.030 (4) | 0.038 (5) | 0.049 (5) | 0.004 (4) | 0.004 (4) | 0.029 (4) |
C25 | 0.023 (4) | 0.034 (4) | 0.038 (4) | 0.002 (3) | 0.002 (3) | 0.019 (4) |
C27 | 0.014 (4) | 0.035 (6) | 0.034 (5) | 0.002 (4) | 0.004 (4) | 0.019 (4) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.116 (3) | C12—C13 | 1.39 |
Zn1—O5i | 2.094 (3) | C12—C17 | 1.39 |
Zn1—O6 | 2.149 (3) | C13—C14 | 1.39 |
Zn1—O9 | 2.134 (3) | C14—C15 | 1.39 |
Zn1—O9ii | 2.091 (3) | C15—C16 | 1.39 |
Zn1—N1 | 2.141 (3) | C16—C17 | 1.39 |
Zn1—Zn2 | 3.108 (1) | C18—C19 | 1.528 (6) |
Zn2—O2 | 1.946 (3) | C20—C27iv | 1.49 (1) |
Zn2—O7 | 1.941 (3) | C20—C21 | 1.510 (9) |
Zn2—O9 | 1.917 (3) | C21—C22 | 1.39 |
Zn2—N2iii | 2.022 (3) | C21—C25 | 1.39 |
O1—C11 | 1.243 (5) | C22—C23 | 1.39 |
O2—C11 | 1.273 (5) | C23—C24 | 1.39 |
O3—C15 | 1.368 (4) | C24—C26 | 1.39 |
O3—C18 | 1.424 (6) | C26—C25 | 1.39 |
O4—C19 | 1.244 (5) | C27—C20iv | 1.49 (1) |
O5—C19 | 1.245 (5) | O9—H9o | 0.98 |
O6—C20 | 1.246 (5) | O1w—H1w1 | 0.88 |
O7—C20 | 1.263 (5) | O1w—H1w2 | 0.88 |
O8—C24 | 1.365 (8) | C1—H1 | 0.93 |
O8—C27 | 1.432 (17) | C2—H2 | 0.93 |
N1—C1 | 1.328 (7) | C4—H4 | 0.93 |
N1—C1' | 1.333 (7) | C5—H5 | 0.93 |
N1—C5 | 1.337 (7) | C6—H6 | 0.93 |
N1—C5' | 1.342 (7) | C7—H7 | 0.93 |
N2—C6' | 1.328 (7) | C9—H9 | 0.93 |
N2—C10' | 1.334 (7) | C10—H10 | 0.93 |
N2—C10 | 1.333 (7) | C1'—H1' | 0.93 |
N2—C6 | 1.337 (7) | C2'—H2' | 0.93 |
C1—C2 | 1.388 (8) | C4'—H4' | 0.93 |
C2—C3 | 1.391 (8) | C5'—H5' | 0.93 |
C3—C2' | 1.382 (8) | C6'—H6' | 0.93 |
C3—C4 | 1.386 (8) | C7'—H7' | 0.93 |
C3—C4' | 1.387 (8) | C9'—H9' | 0.93 |
C3—C8 | 1.479 (5) | C10'—H10' | 0.93 |
C4—C5 | 1.388 (9) | C13—H13 | 0.93 |
C6—C7 | 1.389 (9) | C14—H14 | 0.93 |
C7—C8 | 1.385 (8) | C16—H16 | 0.93 |
C8—C7' | 1.378 (8) | C17—H17 | 0.93 |
C8—C9' | 1.383 (9) | C18—H18a | 0.97 |
C8—C9 | 1.38 (1) | C18—H18b | 0.97 |
C9—C10 | 1.383 (9) | C22—H22 | 0.93 |
C1'—C2' | 1.388 (8) | C23—H23 | 0.93 |
C4'—C5' | 1.389 (9) | C26—H26 | 0.93 |
C6'—C7' | 1.382 (9) | C25—H25 | 0.93 |
C9'—C10' | 1.381 (9) | C27—H27a | 0.97 |
C11—C12 | 1.497 (4) | C27—H27b | 0.97 |
O1—Zn1—O5i | 86.4 (1) | C16—C15—C14 | 120.0 |
O1—Zn1—O6 | 87.0 (1) | C17—C16—C15 | 120.0 |
O1—Zn1—O9 | 97.2 (1) | C16—C17—C12 | 120.0 |
O1—Zn1—O9ii | 175.8 (1) | O3—C18—C19 | 114.5 (4) |
O1—Zn1—N1 | 88.4 (1) | O4—C19—O5 | 127.3 (4) |
O5i—Zn1—O6 | 173.3 (1) | O4—C19—C18 | 115.5 (4) |
O5i—Zn1—O9 | 90.0 (1) | O5—C19—C18 | 117.2 (4) |
O5i—Zn1—O9ii | 97.6 (1) | O6—C20—O7 | 125.8 (4) |
O5i—Zn1—N1 | 88.4 (1) | O6—C20—C27iv | 110.9 (8) |
O6—Zn1—O9 | 91.9 (1) | O7—C20—C27iv | 123.2 (8) |
O6—Zn1—O9ii | 89.1 (1) | O6—C20—C21 | 122.1 (5) |
O9—Zn1—O9ii | 81.5 (1) | O7—C20—C21 | 112.0 (5) |
O9—Zn1—N1 | 174.1 (1) | C22—C21—C25 | 120.0 |
O9ii—Zn1—N1 | 93.1 (1) | C22—C21—C20 | 120.2 (6) |
N1—Zn1—O6 | 90.4 (1) | C25—C21—C20 | 119.6 (6) |
O2—Zn2—O7 | 106.9 (2) | C23—C22—C21 | 120.0 |
O2—Zn2—O9 | 112.9 (1) | C22—C23—C24 | 120.0 |
O2—Zn2—N2iii | 105.3 (1) | O8—C24—C26 | 115.8 (8) |
O7—Zn2—O9 | 110.5 (1) | O8—C24—C23 | 124.2 (8) |
O7—Zn2—N2iii | 105.8 (1) | C26—C24—C23 | 120.0 |
O9—Zn2—N2iii | 114.9 (1) | C24—C26—C25 | 120.0 |
C11—O1—Zn1 | 137.0 (3) | C26—C25—C21 | 120.0 |
C11—O2—Zn2 | 119.6 (3) | O8—C27—C20iv | 110 (1) |
C15—O3—C18 | 117.7 (3) | Zn2—O9—H9o | 107.8 |
C19—O5—Zn1i | 126.3 (3) | Zn1ii—O9—H9o | 107.8 |
C20—O6—Zn1 | 138.5 (3) | Zn1—O9—H9o | 107.8 |
C20—O7—Zn2 | 118.9 (3) | H1w1—O1w—H1w2 | 103.0 |
C24—O8—C27 | 117.3 (9) | N1—C1—H1 | 118.8 |
Zn1ii—O9—Zn1 | 98.5 (1) | C2—C1—H1 | 118.8 |
Zn1—O9—Zn2 | 100.0 (1) | C3—C2—H2 | 119.9 |
Zn1ii—O9—Zn2 | 132.02 (14) | C1—C2—H2 | 119.9 |
C1—N1—C5 | 119.3 (8) | C3—C4—H4 | 119.2 |
C1'—N1—C5 | 112.8 (8) | C5—C4—H4 | 119.2 |
C1—N1—C5' | 112.0 (8) | N1—C5—H5 | 119.7 |
C1'—N1—C5' | 116.4 (8) | C4—C5—H5 | 119.7 |
C1—N1—Zn1 | 120.9 (5) | N2—C6—H6 | 118.0 |
C1'—N1—Zn1 | 124.7 (5) | C7—C6—H6 | 118.0 |
C5—N1—Zn1 | 119.4 (6) | C6—C7—H7 | 120.9 |
C5'—N1—Zn1 | 118.6 (6) | C8—C7—H7 | 120.9 |
C6'—N2—C10' | 118.0 (9) | C10—C9—H9 | 119.8 |
C6'—N2—C10 | 114.2 (9) | C8—C9—H9 | 119.8 |
C10'—N2—C6 | 112.7 (8) | N2—C10—H10 | 118.9 |
C10—N2—C6 | 117.4 (9) | C9—C10—H10 | 118.9 |
C6'—N2—Zn2v | 120.2 (6) | N1—C1'—H1' | 118.2 |
C10'—N2—Zn2v | 121.8 (6) | C2'—C1'—H1' | 118.2 |
C10—N2—Zn2v | 121.6 (6) | C3—C2'—H2' | 120.5 |
C6—N2—Zn2v | 121.0 (7) | C1'—C2'—H2' | 120.5 |
N1—C1—C2 | 122 (1) | C3—C4'—H4' | 121.2 |
C3—C2—C1 | 120 (1) | C5'—C4'—H4' | 121.2 |
C4—C3—C2 | 115.9 (8) | N1—C5'—H5' | 117.7 |
C2'—C3—C4' | 118.9 (8) | C4'—C5'—H5' | 117.7 |
C2'—C3—C8 | 122.2 (6) | N2—C6'—H6' | 119.1 |
C4—C3—C8 | 122.1 (6) | C7'—C6'—H6' | 119.1 |
C2—C3—C8 | 121.9 (6) | C8—C7'—H7' | 119.5 |
C4'—C3—C8 | 118.8 (6) | C6'—C7'—H7' | 119.5 |
C3—C4—C5 | 122 (1) | C10'—C9'—H9' | 120.1 |
N1—C5—C4 | 121 (1) | C8—C9'—H9' | 120.1 |
N2—C6—C7 | 124 (1) | N2—C10'—H10' | 118.5 |
C6—C7—C8 | 118 (1) | C9'—C10'—H10' | 118.5 |
C7'—C8—C9' | 116.5 (9) | C14—C13—H13 | 120.0 |
C7—C8—C9 | 117.8 (9) | C12—C13—H13 | 120.0 |
C7'—C8—C3 | 122.3 (7) | C13—C14—H14 | 120.0 |
C9'—C8—C3 | 121.2 (7) | C15—C14—H14 | 120.0 |
C7—C8—C3 | 121.3 (7) | C17—C16—H16 | 120.0 |
C9—C8—C3 | 120.9 (7) | C15—C16—H16 | 120.0 |
C10—C9—C8 | 120 (1) | C16—C17—H17 | 120.0 |
N2—C10—C9 | 122 (1) | C12—C17—H17 | 120.0 |
N1—C1'—C2' | 124 (1) | O3—C18—H18a | 108.6 |
C3—C2'—C1' | 119 (1) | C19—C18—H18a | 108.6 |
C3—C4'—C5' | 118 (1) | O3—C18—H18b | 108.6 |
N1—C5'—C4' | 125 (1) | C19—C18—H18b | 108.6 |
N2—C6'—C7' | 122 (1) | H18a—C18—H18b | 107.6 |
C8—C7'—C6' | 121 (1) | C23—C22—H22 | 120.0 |
C10'—C9'—C8 | 120 (1) | C21—C22—H22 | 120.0 |
N2—C10'—C9' | 123 (1) | C22—C23—H23 | 120.0 |
O1—C11—O2 | 125.0 (4) | C24—C23—H23 | 120.0 |
O1—C11—C12 | 118.7 (3) | C24—C26—H26 | 120.0 |
O2—C11—C12 | 116.2 (3) | C25—C26—H26 | 120.0 |
C13—C12—C17 | 120.0 | C26—C25—H25 | 120.0 |
C13—C12—C11 | 119.4 (2) | C21—C25—H25 | 120.0 |
C17—C12—C11 | 119.9 (2) | O8—C27—H27a | 109.7 |
C14—C13—C12 | 120.0 | C20iv—C27—H27a | 109.7 |
C13—C14—C15 | 120.0 | O8—C27—H27b | 109.7 |
O3—C15—C16 | 125.0 (2) | C20iv—C27—H27b | 109.7 |
O3—C15—C14 | 114.8 (2) | H27a—C27—H27b | 108.2 |
O5i—Zn1—O1—C11 | −116.3 (5) | C4—C3—C8—C7 | −137.4 (6) |
O9—Zn1—O1—C11 | −26.8 (5) | C2—C3—C8—C7 | 43.7 (7) |
N1—Zn1—O1—C11 | 155.3 (5) | C4—C3—C8—C9 | 44.3 (8) |
O6—Zn1—O1—C11 | 64.8 (5) | C2—C3—C8—C9 | −134.5 (6) |
O9—Zn2—O2—C11 | 49.7 (4) | C7—C8—C9—C10 | 0.2 (8) |
O7—Zn2—O2—C11 | −72.0 (4) | C3—C8—C9—C10 | 178.6 (5) |
N2iii—Zn2—O2—C11 | 175.8 (3) | C6—N2—C10—C9 | 0.0 (7) |
O9ii—Zn1—O6—C20 | 99.0 (4) | Zn2v—N2—C10—C9 | 179.6 (5) |
O1—Zn1—O6—C20 | −79.5 (4) | C8—C9—C10—N2 | −0.1 (9) |
O9—Zn1—O6—C20 | 17.5 (4) | C5'—N1—C1'—C2' | −0.2 (3) |
N1—Zn1—O6—C20 | −167.9 (4) | Zn1—N1—C1'—C2' | −173.4 (3) |
O9—Zn2—O7—C20 | −40.4 (3) | C4'—C3—C2'—C1' | 0.8 (6) |
O2—Zn2—O7—C20 | 82.8 (3) | C8—C3—C2'—C1' | 177.7 (4) |
N2iii—Zn2—O7—C20 | −165.3 (3) | N1—C1'—C2'—C3 | −0.3 (3) |
O7—Zn2—O9—Zn1ii | −47.5 (2) | C2'—C3—C4'—C5' | −0.8 (8) |
O2—Zn2—O9—Zn1ii | −167.1 (2) | C1'—N1—C5'—C4' | 0.2 (7) |
N2iii—Zn2—O9—Zn1ii | 72.1 (2) | Zn1—N1—C5'—C4' | 173.8 (5) |
O7—Zn2—O9—Zn1 | 63.8 (2) | C3—C4'—C5'—N1 | 0.2 (9) |
O2—Zn2—O9—Zn1 | −55.8 (2) | C10'—N2—C6'—C7' | −0.5 (3) |
N2iii—Zn2—O9—Zn1 | −176.6 (1) | Zn2v—N2—C6'—C7' | −178.9 (3) |
O9ii—Zn1—O9—Zn2 | −135.6 (2) | C9'—C8—C7'—C6' | 1.8 (6) |
O5i—Zn1—O9—Zn2 | 126.8 (1) | C3—C8—C7'—C6' | −177.9 (4) |
O1—Zn1—O9—Zn2 | 40.5 (1) | N2—C6'—C7'—C8 | −0.7 (3) |
O6—Zn1—O9—Zn2 | −46.8 (1) | C7'—C8—C9'—C10' | −1.6 (8) |
O9ii—Zn1—O9—Zn1ii | 0.0 | C3—C8—C9'—C10' | 178.0 (5) |
O5i—Zn1—O9—Zn1ii | −97.7 (1) | C6'—N2—C10'—C9' | 0.7 (7) |
O1—Zn1—O9—Zn1ii | 176.0 (1) | Zn2v—N2—C10'—C9' | 179.1 (5) |
O6—Zn1—O9—Zn1ii | 88.8 (1) | C8—C9'—C10'—N2 | 0.4 (9) |
O9ii—Zn1—N1—C1 | 48.7 (4) | Zn1—O1—C11—O2 | 15.2 (7) |
O5i—Zn1—N1—C1 | 146.2 (4) | Zn1—O1—C11—C12 | −162.8 (3) |
O1—Zn1—N1—C1 | −127.4 (4) | Zn2—O2—C11—O1 | −22.5 (6) |
O6—Zn1—N1—C1 | −40.4 (4) | Zn2—O2—C11—C12 | 155.5 (3) |
O9ii—Zn1—N1—C1' | 76.4 (4) | O1—C11—C12—C13 | 172.9 (3) |
O5i—Zn1—N1—C1' | 173.9 (4) | O2—C11—C12—C13 | −5.2 (5) |
O1—Zn1—N1—C1' | −99.7 (4) | O1—C11—C12—C17 | 2.4 (5) |
O6—Zn1—N1—C1' | −12.7 (4) | O2—C11—C12—C17 | −175.8 (3) |
O9ii—Zn1—N1—C5 | −124.9 (4) | C11—C12—C13—C14 | −170.5 (3) |
O5i—Zn1—N1—C5 | −27.4 (4) | C18—O3—C15—C16 | −4.6 (5) |
O1—Zn1—N1—C5 | 59.0 (4) | C18—O3—C15—C14 | −179.6 (3) |
O6—Zn1—N1—C5 | 146.0 (4) | C13—C14—C15—O3 | 175.2 (3) |
O9ii—Zn1—N1—C5' | −96.7 (4) | O3—C15—C16—C17 | −174.7 (3) |
O5i—Zn1—N1—C5' | 0.8 (4) | C11—C12—C17—C16 | 170.5 (3) |
O1—Zn1—N1—C5' | 87.2 (4) | C15—O3—C18—C19 | −75.3 (5) |
O6—Zn1—N1—C5' | 174.2 (4) | Zn1i—O5—C19—O4 | −21.3 (6) |
C1'—N1—C1—C2 | 80 (2) | Zn1i—O5—C19—C18 | 161.4 (3) |
C5—N1—C1—C2 | 0.4 (3) | O3—C18—C19—O4 | 155.8 (4) |
C5'—N1—C1—C2 | −25.7 (6) | O3—C18—C19—O5 | −26.6 (6) |
Zn1—N1—C1—C2 | −173.2 (3) | Zn1—O6—C20—O7 | 13.4 (7) |
N1—C1—C2—C3 | 0.9 (3) | Zn1—O6—C20—C27iv | −165.8 (7) |
C1—C2—C3—C4 | −2.2 (6) | Zn1—O6—C20—C21 | −167.1 (6) |
C1—C2—C3—C8 | 176.7 (4) | Zn2—O7—C20—O6 | −3.1 (6) |
C2—C3—C4—C5 | 2.3 (8) | Zn2—O7—C20—C27iv | 176.0 (8) |
C8—C3—C4—C5 | −176.6 (5) | Zn2—O7—C20—C21 | 177.4 (5) |
C1—N1—C5—C4 | −0.3 (7) | O6—C20—C21—C22 | −177.2 (5) |
Zn1—N1—C5—C4 | 173.4 (5) | O7—C20—C21—C22 | 2.4 (8) |
C3—C4—C5—N1 | −1.1 (9) | C27iv—C20—C21—C22 | 176 (5) |
C10—N2—C6—C7 | 0.0 (3) | O6—C20—C21—C25 | 8.0 (9) |
Zn2v—N2—C6—C7 | −179.6 (3) | O7—C20—C21—C25 | −172.5 (5) |
N2—C6—C7—C8 | 0.1 (3) | C27iv—C20—C21—C25 | 1 (5) |
C6—C7—C8—C9 | −0.2 (6) | C20—C21—C22—C23 | −174.8 (9) |
C6—C7—C8—C3 | −178.5 (4) | C27—O8—C24—C26 | 173 (1) |
C4—C3—C8—C7' | −161.5 (6) | C27—O8—C24—C23 | −5 (1) |
C2—C3—C8—C7' | 19.7 (7) | C22—C23—C24—O8 | 178 (1) |
C4'—C3—C8—C7' | 169.5 (6) | O8—C24—C26—C25 | −178 (1) |
C2'—C3—C8—C9' | 173.1 (6) | C20—C21—C25—C26 | 174.9 (9) |
C4'—C3—C8—C9' | −10.1 (8) | C24—O8—C27—C20iv | 175 (1) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z+1; (iv) −x+2, −y+2, −z+2; (v) x−1, y, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9o···O4i | 0.98 | 1.83 | 2.701 (4) | 147 |
O1w—H1w1···O4 | 0.88 | 1.92 | 2.798 (9) | 176 |
O1w—H1w2···O4vi | 0.88 | 2.02 | 2.902 (9) | 176 |
Symmetry codes: (i) −x+1, −y, −z+1; (vi) −x+1, −y, −z. |