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
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.051
- wR factor = 0.128
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 12 PLAT301_ALERT_3_C Main Residue Disorder ......................... 25.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: 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. |