In the title compound, [Zn(C5H2N2O4)(C10H8N2)]n, the ZnII atom is six-coordinated in an octahedral geometry by two carboxylate O atoms and two N atoms from two imidazole-4,5-dicarboxylate ligands, and two N atoms from a 2,2′-bipyridine ligand. The asymmetric unit contains two formula units. The imidazole-4,5-dicarboxylate ligand bridges two ZnII atoms to form a one-dimensional zigzag chain structure.
Supporting information
CCDC reference: 1296347
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C)= 0.003 Å
- R factor = 0.029
- wR factor = 0.074
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
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Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.
catena-Poly[[(2,2'-bipyridine-
κ2N,
N')zinc(II)]-
µ-imidazole-4,5-dicarboxylato-
κ4N1,
O5:
N3,
O4]
top
Crystal data top
[Zn(C5H2N2O4)(C10H8N2)] | F(000) = 1520 |
Mr = 375.64 | Dx = 1.746 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5520 reflections |
a = 20.470 (1) Å | θ = 2.3–26.0° |
b = 9.6494 (5) Å | µ = 1.75 mm−1 |
c = 14.7843 (7) Å | T = 292 K |
β = 101.783 (1)° | Block, colorless |
V = 2858.7 (2) Å3 | 0.27 × 0.23 × 0.21 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 5621 independent reflections |
Radiation source: fine-focus sealed tube | 4913 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2001) | h = −25→20 |
Tmin = 0.629, Tmax = 0.691 | k = −11→10 |
15264 measured reflections | l = −17→18 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0391P)2 + 1.2625P] where P = (Fo2 + 2Fc2)/3 |
5621 reflections | (Δ/σ)max = 0.001 |
433 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
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 | |
Zn1 | 0.097901 (12) | 0.59581 (3) | 0.319707 (17) | 0.01956 (8) | |
Zn2 | 0.399412 (11) | 0.47522 (3) | 0.714412 (16) | 0.01726 (8) | |
C1 | −0.02127 (10) | 0.3690 (2) | 0.27867 (15) | 0.0198 (4) | |
H1 | −0.0347 | 0.3688 | 0.3351 | 0.024* | |
C4 | 0.08027 (11) | 0.4931 (2) | 0.12798 (15) | 0.0206 (5) | |
C27 | 0.18385 (12) | 0.4734 (3) | 0.62208 (17) | 0.0323 (6) | |
H27 | 0.1523 | 0.5389 | 0.5957 | 0.039* | |
C14 | 0.26992 (12) | 0.8757 (2) | 0.36444 (15) | 0.0244 (5) | |
H14 | 0.2768 | 0.9699 | 0.3567 | 0.029* | |
O6 | 0.46696 (7) | 0.63637 (16) | 0.48931 (9) | 0.0209 (3) | |
O5 | 0.41454 (7) | 0.49639 (15) | 0.57124 (10) | 0.0185 (3) | |
C16 | 0.52318 (10) | 0.6783 (2) | 0.79889 (14) | 0.0184 (4) | |
H16 | 0.5253 | 0.6689 | 0.8620 | 0.022* | |
C29 | 0.21219 (12) | 0.2442 (3) | 0.67708 (18) | 0.0335 (6) | |
H29 | 0.2001 | 0.1547 | 0.6902 | 0.040* | |
O1 | 0.08405 (8) | 0.45828 (17) | 0.04491 (10) | 0.0250 (4) | |
O2 | 0.11830 (8) | 0.57759 (16) | 0.17576 (11) | 0.0244 (3) | |
C30 | 0.27827 (11) | 0.2847 (2) | 0.69560 (16) | 0.0252 (5) | |
H30 | 0.3107 | 0.2198 | 0.7200 | 0.030* | |
N8 | 0.55730 (9) | 0.77603 (18) | 0.76236 (11) | 0.0173 (4) | |
C15 | 0.20630 (11) | 0.8209 (2) | 0.34595 (15) | 0.0237 (5) | |
H15 | 0.1705 | 0.8799 | 0.3249 | 0.028* | |
C26 | 0.25108 (11) | 0.5085 (2) | 0.64542 (14) | 0.0208 (5) | |
N2 | −0.04569 (8) | 0.28124 (18) | 0.20963 (12) | 0.0184 (4) | |
C12 | 0.31098 (11) | 0.6491 (2) | 0.40568 (15) | 0.0248 (5) | |
H12 | 0.3463 | 0.5883 | 0.4253 | 0.030* | |
N7 | 0.48589 (9) | 0.59596 (18) | 0.73549 (12) | 0.0171 (4) | |
N5 | 0.34006 (9) | 0.67336 (19) | 0.67812 (12) | 0.0219 (4) | |
N3 | 0.16331 (9) | 0.42239 (19) | 0.37696 (13) | 0.0205 (4) | |
N1 | 0.02439 (9) | 0.45712 (18) | 0.25850 (12) | 0.0184 (4) | |
N6 | 0.29768 (9) | 0.41348 (19) | 0.67987 (12) | 0.0199 (4) | |
N4 | 0.19397 (9) | 0.68611 (18) | 0.35704 (12) | 0.0196 (4) | |
C2 | −0.01343 (10) | 0.3154 (2) | 0.14047 (14) | 0.0182 (4) | |
C17 | 0.54077 (10) | 0.7531 (2) | 0.66909 (14) | 0.0161 (4) | |
C9 | 0.27634 (11) | 0.3555 (2) | 0.43767 (15) | 0.0243 (5) | |
H9 | 0.3212 | 0.3794 | 0.4539 | 0.029* | |
C19 | 0.45729 (10) | 0.5860 (2) | 0.56654 (14) | 0.0169 (4) | |
C18 | 0.49727 (10) | 0.6431 (2) | 0.65252 (14) | 0.0167 (4) | |
C24 | 0.23366 (12) | 0.7599 (3) | 0.60140 (17) | 0.0306 (6) | |
H24 | 0.1890 | 0.7430 | 0.5754 | 0.037* | |
C11 | 0.24583 (11) | 0.6010 (2) | 0.38736 (14) | 0.0193 (5) | |
C6 | 0.14443 (12) | 0.2930 (2) | 0.38996 (16) | 0.0264 (5) | |
H6 | 0.0993 | 0.2714 | 0.3740 | 0.032* | |
C3 | 0.02966 (10) | 0.4231 (2) | 0.17031 (14) | 0.0173 (4) | |
C28 | 0.16437 (12) | 0.3401 (3) | 0.63858 (19) | 0.0385 (6) | |
H28 | 0.1196 | 0.3153 | 0.6239 | 0.046* | |
C25 | 0.27549 (11) | 0.6523 (2) | 0.63946 (14) | 0.0216 (5) | |
C8 | 0.25607 (12) | 0.2218 (2) | 0.44974 (16) | 0.0279 (5) | |
H8 | 0.2872 | 0.1541 | 0.4735 | 0.033* | |
C7 | 0.18875 (12) | 0.1893 (2) | 0.42605 (17) | 0.0283 (5) | |
H7 | 0.1738 | 0.1001 | 0.4342 | 0.034* | |
C10 | 0.22865 (11) | 0.4543 (2) | 0.40084 (14) | 0.0199 (5) | |
C21 | 0.36413 (12) | 0.8021 (2) | 0.67954 (17) | 0.0289 (5) | |
H21 | 0.4087 | 0.8170 | 0.7069 | 0.035* | |
C13 | 0.32285 (11) | 0.7883 (3) | 0.39455 (16) | 0.0266 (5) | |
H13 | 0.3662 | 0.8225 | 0.4073 | 0.032* | |
C23 | 0.25949 (14) | 0.8922 (3) | 0.60283 (19) | 0.0369 (6) | |
H23 | 0.2325 | 0.9657 | 0.5775 | 0.044* | |
C22 | 0.32590 (14) | 0.9144 (3) | 0.64225 (19) | 0.0364 (6) | |
H22 | 0.3444 | 1.0026 | 0.6437 | 0.044* | |
O7 | 0.55437 (8) | 0.81893 (17) | 0.52023 (10) | 0.0295 (4) | |
H7A | 0.5255 | 0.7587 | 0.5099 | 0.044* | |
O4 | 0.00496 (8) | 0.26604 (17) | −0.00931 (10) | 0.0273 (4) | |
H4A | 0.0310 | 0.3295 | 0.0090 | 0.041* | |
C20 | 0.56730 (10) | 0.8472 (2) | 0.60587 (14) | 0.0195 (4) | |
C5 | −0.02691 (11) | 0.2338 (2) | 0.05391 (15) | 0.0205 (5) | |
O8 | 0.60134 (8) | 0.94846 (16) | 0.64083 (10) | 0.0218 (3) | |
O3 | −0.06777 (8) | 0.13640 (16) | 0.04731 (10) | 0.0251 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.01433 (14) | 0.01608 (14) | 0.02600 (15) | 0.00008 (9) | −0.00125 (10) | −0.00087 (10) |
Zn2 | 0.01451 (14) | 0.01593 (14) | 0.02065 (14) | 0.00018 (9) | 0.00196 (10) | 0.00301 (10) |
C1 | 0.0177 (11) | 0.0215 (11) | 0.0195 (10) | −0.0009 (9) | 0.0025 (8) | 0.0004 (9) |
C4 | 0.0166 (11) | 0.0198 (11) | 0.0252 (11) | 0.0047 (9) | 0.0041 (9) | 0.0029 (9) |
C27 | 0.0182 (12) | 0.0417 (15) | 0.0350 (13) | 0.0048 (11) | 0.0004 (10) | −0.0003 (12) |
C14 | 0.0287 (13) | 0.0199 (12) | 0.0244 (11) | −0.0063 (10) | 0.0049 (9) | 0.0016 (9) |
O6 | 0.0222 (8) | 0.0241 (8) | 0.0155 (7) | −0.0024 (6) | 0.0017 (6) | −0.0005 (6) |
O5 | 0.0166 (8) | 0.0198 (8) | 0.0183 (7) | −0.0038 (6) | 0.0016 (6) | −0.0027 (6) |
C16 | 0.0199 (11) | 0.0197 (11) | 0.0147 (10) | 0.0005 (9) | 0.0017 (8) | 0.0007 (8) |
C29 | 0.0295 (14) | 0.0316 (14) | 0.0387 (14) | −0.0111 (11) | 0.0054 (11) | −0.0033 (11) |
O1 | 0.0250 (9) | 0.0273 (9) | 0.0248 (8) | −0.0004 (7) | 0.0099 (7) | −0.0005 (7) |
O2 | 0.0182 (8) | 0.0256 (9) | 0.0298 (8) | −0.0056 (7) | 0.0060 (7) | −0.0012 (7) |
C30 | 0.0233 (12) | 0.0224 (12) | 0.0287 (12) | −0.0025 (9) | 0.0025 (9) | −0.0001 (10) |
N8 | 0.0182 (9) | 0.0175 (9) | 0.0155 (8) | −0.0010 (7) | 0.0022 (7) | −0.0020 (7) |
C15 | 0.0234 (12) | 0.0198 (12) | 0.0270 (11) | 0.0005 (9) | 0.0034 (9) | 0.0033 (9) |
C26 | 0.0178 (11) | 0.0272 (12) | 0.0169 (10) | 0.0026 (9) | 0.0024 (9) | −0.0010 (9) |
N2 | 0.0157 (9) | 0.0198 (9) | 0.0186 (9) | −0.0010 (7) | 0.0012 (7) | 0.0008 (7) |
C12 | 0.0184 (11) | 0.0250 (12) | 0.0289 (12) | 0.0007 (9) | −0.0001 (9) | 0.0051 (10) |
N7 | 0.0182 (9) | 0.0166 (9) | 0.0159 (9) | −0.0015 (7) | 0.0022 (7) | 0.0003 (7) |
N5 | 0.0205 (10) | 0.0210 (10) | 0.0251 (10) | 0.0028 (8) | 0.0065 (8) | 0.0014 (8) |
N3 | 0.0168 (9) | 0.0189 (10) | 0.0249 (9) | −0.0009 (7) | 0.0025 (7) | 0.0018 (8) |
N1 | 0.0148 (9) | 0.0193 (10) | 0.0197 (9) | 0.0003 (7) | 0.0004 (7) | −0.0010 (7) |
N6 | 0.0169 (9) | 0.0227 (10) | 0.0199 (9) | 0.0002 (7) | 0.0039 (7) | 0.0012 (7) |
N4 | 0.0165 (9) | 0.0186 (10) | 0.0224 (9) | −0.0010 (7) | 0.0007 (7) | 0.0002 (7) |
C2 | 0.0148 (10) | 0.0192 (11) | 0.0195 (10) | 0.0023 (8) | 0.0010 (8) | 0.0006 (8) |
C17 | 0.0148 (10) | 0.0167 (11) | 0.0166 (10) | 0.0005 (8) | 0.0025 (8) | −0.0005 (8) |
C9 | 0.0184 (11) | 0.0264 (12) | 0.0260 (11) | 0.0025 (9) | −0.0004 (9) | −0.0005 (10) |
C19 | 0.0147 (10) | 0.0171 (11) | 0.0187 (10) | 0.0029 (8) | 0.0030 (8) | −0.0010 (8) |
C18 | 0.0150 (10) | 0.0178 (11) | 0.0167 (10) | 0.0016 (8) | 0.0016 (8) | 0.0009 (8) |
C24 | 0.0255 (13) | 0.0359 (15) | 0.0308 (13) | 0.0115 (11) | 0.0065 (10) | 0.0075 (11) |
C11 | 0.0187 (11) | 0.0210 (12) | 0.0177 (10) | −0.0001 (9) | 0.0021 (8) | 0.0000 (8) |
C6 | 0.0216 (12) | 0.0246 (12) | 0.0324 (12) | −0.0034 (10) | 0.0044 (10) | 0.0023 (10) |
C3 | 0.0137 (10) | 0.0170 (11) | 0.0203 (10) | 0.0031 (8) | 0.0013 (8) | 0.0009 (8) |
C28 | 0.0181 (12) | 0.0455 (17) | 0.0495 (16) | −0.0076 (11) | 0.0011 (11) | −0.0085 (13) |
C25 | 0.0217 (11) | 0.0261 (12) | 0.0184 (10) | 0.0061 (9) | 0.0072 (9) | 0.0029 (9) |
C8 | 0.0284 (13) | 0.0219 (12) | 0.0306 (13) | 0.0076 (10) | −0.0001 (10) | 0.0034 (10) |
C7 | 0.0308 (13) | 0.0170 (11) | 0.0362 (13) | −0.0011 (10) | 0.0047 (11) | 0.0042 (10) |
C10 | 0.0189 (11) | 0.0217 (12) | 0.0182 (10) | −0.0008 (9) | 0.0017 (8) | −0.0009 (9) |
C21 | 0.0278 (13) | 0.0256 (13) | 0.0358 (13) | 0.0026 (10) | 0.0124 (11) | −0.0007 (10) |
C13 | 0.0190 (12) | 0.0315 (13) | 0.0283 (12) | −0.0073 (10) | 0.0022 (9) | 0.0023 (10) |
C23 | 0.0399 (16) | 0.0292 (15) | 0.0442 (15) | 0.0185 (12) | 0.0146 (13) | 0.0108 (12) |
C22 | 0.0454 (17) | 0.0196 (13) | 0.0490 (16) | 0.0064 (11) | 0.0207 (13) | 0.0044 (11) |
O7 | 0.0393 (10) | 0.0307 (9) | 0.0191 (8) | −0.0170 (8) | 0.0074 (7) | −0.0019 (7) |
O4 | 0.0296 (9) | 0.0293 (9) | 0.0230 (8) | −0.0035 (7) | 0.0054 (7) | −0.0054 (7) |
C20 | 0.0191 (11) | 0.0201 (11) | 0.0190 (10) | −0.0011 (9) | 0.0036 (8) | 0.0005 (9) |
C5 | 0.0177 (11) | 0.0207 (12) | 0.0212 (11) | 0.0033 (9) | −0.0006 (9) | −0.0001 (9) |
O8 | 0.0246 (8) | 0.0206 (8) | 0.0210 (8) | −0.0073 (7) | 0.0065 (6) | −0.0011 (6) |
O3 | 0.0248 (9) | 0.0241 (8) | 0.0248 (8) | −0.0040 (7) | 0.0014 (7) | −0.0052 (7) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.0780 (17) | C12—C13 | 1.381 (3) |
Zn1—N2i | 2.0839 (18) | C12—C11 | 1.385 (3) |
Zn1—N4 | 2.1185 (18) | C12—H12 | 0.9300 |
Zn1—N3 | 2.2015 (18) | N7—C18 | 1.372 (3) |
Zn1—O3i | 2.2124 (16) | N5—C21 | 1.335 (3) |
Zn1—O2 | 2.2577 (16) | N5—C25 | 1.344 (3) |
Zn2—N7 | 2.0888 (17) | N3—C6 | 1.333 (3) |
Zn2—N8ii | 2.1150 (17) | N3—C10 | 1.348 (3) |
Zn2—N6 | 2.1256 (18) | N1—C3 | 1.370 (3) |
Zn2—O8ii | 2.1588 (15) | N4—C11 | 1.344 (3) |
Zn2—O5 | 2.2104 (14) | C2—C3 | 1.376 (3) |
Zn2—N5 | 2.2701 (18) | C2—C5 | 1.480 (3) |
C1—N1 | 1.341 (3) | C17—C18 | 1.375 (3) |
C1—N2 | 1.342 (3) | C17—C20 | 1.483 (3) |
C1—H1 | 0.9300 | C9—C8 | 1.378 (3) |
C4—O2 | 1.243 (3) | C9—C10 | 1.394 (3) |
C4—O1 | 1.291 (3) | C9—H9 | 0.9300 |
C4—C3 | 1.479 (3) | C19—C18 | 1.471 (3) |
C27—C28 | 1.383 (4) | C24—C23 | 1.381 (4) |
C27—C26 | 1.391 (3) | C24—C25 | 1.389 (3) |
C27—H27 | 0.9300 | C24—H24 | 0.9300 |
C14—C13 | 1.374 (3) | C11—C10 | 1.482 (3) |
C14—C15 | 1.380 (3) | C6—C7 | 1.382 (3) |
C14—H14 | 0.9300 | C6—H6 | 0.9300 |
O6—C19 | 1.293 (3) | C28—H28 | 0.9300 |
O5—C19 | 1.242 (2) | C8—C7 | 1.387 (3) |
C16—N7 | 1.342 (3) | C8—H8 | 0.9300 |
C16—N8 | 1.350 (3) | C7—H7 | 0.9300 |
C16—H16 | 0.9300 | C21—C22 | 1.384 (3) |
C29—C30 | 1.380 (3) | C21—H21 | 0.9300 |
C29—C28 | 1.382 (4) | C13—H13 | 0.9300 |
C29—H29 | 0.9300 | C23—C22 | 1.382 (4) |
C30—N6 | 1.340 (3) | C23—H23 | 0.9300 |
C30—H30 | 0.9300 | C22—H22 | 0.9300 |
N8—C17 | 1.369 (3) | O7—C20 | 1.269 (3) |
N8—Zn2iii | 2.1150 (17) | O7—H7A | 0.8200 |
C15—N4 | 1.341 (3) | O4—C5 | 1.283 (3) |
C15—H15 | 0.9300 | O4—H4A | 0.8200 |
C26—N6 | 1.346 (3) | C20—O8 | 1.249 (3) |
C26—C25 | 1.483 (3) | C5—O3 | 1.249 (3) |
N2—C2 | 1.366 (3) | O8—Zn2iii | 2.1588 (15) |
N2—Zn1iv | 2.0839 (18) | O3—Zn1iv | 2.2124 (16) |
| | | |
N1—Zn1—N2i | 99.63 (7) | C6—N3—Zn1 | 126.60 (15) |
N1—Zn1—N4 | 158.35 (7) | C10—N3—Zn1 | 114.83 (14) |
N2i—Zn1—N4 | 96.34 (7) | C1—N1—C3 | 104.70 (17) |
N1—Zn1—N3 | 90.42 (7) | C1—N1—Zn1 | 141.89 (15) |
N2i—Zn1—N3 | 168.09 (7) | C3—N1—Zn1 | 112.21 (14) |
N4—Zn1—N3 | 75.71 (7) | C30—N6—C26 | 119.05 (19) |
N1—Zn1—O3i | 101.10 (6) | C30—N6—Zn2 | 121.94 (15) |
N2i—Zn1—O3i | 78.97 (6) | C26—N6—Zn2 | 118.93 (15) |
N4—Zn1—O3i | 96.21 (6) | C15—N4—C11 | 118.53 (19) |
N3—Zn1—O3i | 92.92 (6) | C15—N4—Zn1 | 123.70 (15) |
N1—Zn1—O2 | 78.24 (6) | C11—N4—Zn1 | 117.60 (14) |
N2i—Zn1—O2 | 93.23 (6) | N2—C2—C3 | 108.57 (18) |
N4—Zn1—O2 | 86.39 (6) | N2—C2—C5 | 119.06 (19) |
N3—Zn1—O2 | 95.06 (6) | C3—C2—C5 | 132.3 (2) |
O3i—Zn1—O2 | 172.00 (6) | N8—C17—C18 | 108.79 (18) |
N7—Zn2—N8ii | 99.70 (7) | N8—C17—C20 | 119.25 (18) |
N7—Zn2—N6 | 162.00 (7) | C18—C17—C20 | 131.87 (19) |
N8ii—Zn2—N6 | 98.15 (7) | C8—C9—C10 | 119.1 (2) |
N7—Zn2—O8ii | 95.52 (6) | C8—C9—H9 | 120.5 |
N8ii—Zn2—O8ii | 79.51 (6) | C10—C9—H9 | 120.5 |
N6—Zn2—O8ii | 89.98 (6) | O5—C19—O6 | 123.21 (19) |
N7—Zn2—O5 | 79.11 (6) | O5—C19—C18 | 119.09 (18) |
N8ii—Zn2—O5 | 95.94 (6) | O6—C19—C18 | 117.65 (18) |
N6—Zn2—O5 | 96.77 (6) | N7—C18—C17 | 108.58 (17) |
O8ii—Zn2—O5 | 172.37 (6) | N7—C18—C19 | 118.85 (18) |
N7—Zn2—N5 | 87.81 (7) | C17—C18—C19 | 131.97 (19) |
N8ii—Zn2—N5 | 171.91 (7) | C23—C24—C25 | 118.8 (2) |
N6—Zn2—N5 | 74.24 (7) | C23—C24—H24 | 120.6 |
O8ii—Zn2—N5 | 102.90 (6) | C25—C24—H24 | 120.6 |
O5—Zn2—N5 | 82.46 (6) | N4—C11—C12 | 121.6 (2) |
N1—C1—N2 | 113.52 (19) | N4—C11—C10 | 115.81 (19) |
N1—C1—H1 | 123.2 | C12—C11—C10 | 122.6 (2) |
N2—C1—H1 | 123.2 | N3—C6—C7 | 123.2 (2) |
O2—C4—O1 | 124.0 (2) | N3—C6—H6 | 118.4 |
O2—C4—C3 | 118.1 (2) | C7—C6—H6 | 118.4 |
O1—C4—C3 | 117.83 (19) | N1—C3—C2 | 108.43 (18) |
C28—C27—C26 | 119.3 (2) | N1—C3—C4 | 119.44 (19) |
C28—C27—H27 | 120.4 | C2—C3—C4 | 131.9 (2) |
C26—C27—H27 | 120.4 | C29—C28—C27 | 119.3 (2) |
C13—C14—C15 | 118.6 (2) | C29—C28—H28 | 120.3 |
C13—C14—H14 | 120.7 | C27—C28—H28 | 120.3 |
C15—C14—H14 | 120.7 | N5—C25—C24 | 122.0 (2) |
C19—O5—Zn2 | 110.85 (12) | N5—C25—C26 | 115.46 (19) |
N7—C16—N8 | 113.64 (18) | C24—C25—C26 | 122.4 (2) |
N7—C16—H16 | 123.2 | C9—C8—C7 | 119.3 (2) |
N8—C16—H16 | 123.2 | C9—C8—H8 | 120.4 |
C30—C29—C28 | 118.4 (2) | C7—C8—H8 | 120.4 |
C30—C29—H29 | 120.8 | C6—C7—C8 | 118.3 (2) |
C28—C29—H29 | 120.8 | C6—C7—H7 | 120.8 |
C4—O2—Zn1 | 111.83 (14) | C8—C7—H7 | 120.8 |
N6—C30—C29 | 122.8 (2) | N3—C10—C9 | 121.6 (2) |
N6—C30—H30 | 118.6 | N3—C10—C11 | 115.69 (19) |
C29—C30—H30 | 118.6 | C9—C10—C11 | 122.7 (2) |
C16—N8—C17 | 104.38 (17) | N5—C21—C22 | 123.1 (2) |
C16—N8—Zn2iii | 143.48 (14) | N5—C21—H21 | 118.5 |
C17—N8—Zn2iii | 108.64 (13) | C22—C21—H21 | 118.5 |
N4—C15—C14 | 122.8 (2) | C14—C13—C12 | 119.3 (2) |
N4—C15—H15 | 118.6 | C14—C13—H13 | 120.3 |
C14—C15—H15 | 118.6 | C12—C13—H13 | 120.3 |
N6—C26—C27 | 121.1 (2) | C24—C23—C22 | 119.4 (2) |
N6—C26—C25 | 116.01 (19) | C24—C23—H23 | 120.3 |
C27—C26—C25 | 122.8 (2) | C22—C23—H23 | 120.3 |
C1—N2—C2 | 104.78 (17) | C23—C22—C21 | 118.3 (2) |
C1—N2—Zn1iv | 142.73 (15) | C23—C22—H22 | 120.8 |
C2—N2—Zn1iv | 110.93 (13) | C21—C22—H22 | 120.8 |
C13—C12—C11 | 119.2 (2) | C20—O7—H7A | 109.5 |
C13—C12—H12 | 120.4 | C5—O4—H4A | 109.5 |
C11—C12—H12 | 120.4 | O8—C20—O7 | 124.5 (2) |
C16—N7—C18 | 104.60 (17) | O8—C20—C17 | 117.60 (18) |
C16—N7—Zn2 | 141.11 (15) | O7—C20—C17 | 117.94 (19) |
C18—N7—Zn2 | 110.18 (13) | O3—C5—O4 | 123.9 (2) |
C21—N5—C25 | 118.36 (19) | O3—C5—C2 | 118.15 (19) |
C21—N5—Zn2 | 127.02 (15) | O4—C5—C2 | 117.94 (19) |
C25—N5—Zn2 | 113.93 (14) | C20—O8—Zn2iii | 112.79 (13) |
C6—N3—C10 | 118.56 (19) | C5—O3—Zn1iv | 111.57 (13) |
| | | |
N7—Zn2—O5—C19 | −11.92 (14) | O2—Zn1—N4—C11 | −90.68 (16) |
N8ii—Zn2—O5—C19 | −110.69 (14) | C1—N2—C2—C3 | 0.1 (2) |
N6—Zn2—O5—C19 | 150.35 (14) | Zn1iv—N2—C2—C3 | −169.07 (13) |
N5—Zn2—O5—C19 | 77.30 (14) | C1—N2—C2—C5 | 177.65 (18) |
O1—C4—O2—Zn1 | −176.07 (16) | Zn1iv—N2—C2—C5 | 8.5 (2) |
C3—C4—O2—Zn1 | 0.8 (2) | C16—N8—C17—C18 | 0.2 (2) |
N1—Zn1—O2—C4 | −2.57 (15) | Zn2iii—N8—C17—C18 | −163.96 (14) |
N2i—Zn1—O2—C4 | −101.74 (15) | C16—N8—C17—C20 | 177.20 (18) |
N4—Zn1—O2—C4 | 162.10 (15) | Zn2iii—N8—C17—C20 | 13.0 (2) |
N3—Zn1—O2—C4 | 86.81 (15) | Zn2—O5—C19—O6 | −167.14 (16) |
C28—C29—C30—N6 | 1.6 (4) | Zn2—O5—C19—C18 | 10.1 (2) |
N7—C16—N8—C17 | −0.5 (2) | C16—N7—C18—C17 | −0.4 (2) |
N7—C16—N8—Zn2iii | 153.75 (18) | Zn2—N7—C18—C17 | 161.89 (14) |
C13—C14—C15—N4 | 0.7 (3) | C16—N7—C18—C19 | −172.54 (18) |
C28—C27—C26—N6 | 3.0 (4) | Zn2—N7—C18—C19 | −10.2 (2) |
C28—C27—C26—C25 | −173.3 (2) | N8—C17—C18—N7 | 0.1 (2) |
N1—C1—N2—C2 | 0.0 (2) | C20—C17—C18—N7 | −176.3 (2) |
N1—C1—N2—Zn1iv | 163.13 (17) | N8—C17—C18—C19 | 170.8 (2) |
N8—C16—N7—C18 | 0.6 (2) | C20—C17—C18—C19 | −5.6 (4) |
N8—C16—N7—Zn2 | −152.40 (17) | O5—C19—C18—N7 | −0.3 (3) |
N8ii—Zn2—N7—C16 | −102.5 (2) | O6—C19—C18—N7 | 177.10 (18) |
N6—Zn2—N7—C16 | 85.0 (3) | O5—C19—C18—C17 | −170.2 (2) |
O8ii—Zn2—N7—C16 | −22.2 (2) | O6—C19—C18—C17 | 7.2 (3) |
O5—Zn2—N7—C16 | 163.3 (2) | C15—N4—C11—C12 | −1.0 (3) |
N5—Zn2—N7—C16 | 80.5 (2) | Zn1—N4—C11—C12 | 174.34 (16) |
N8ii—Zn2—N7—C18 | 105.44 (14) | C15—N4—C11—C10 | 178.20 (19) |
N6—Zn2—N7—C18 | −67.0 (3) | Zn1—N4—C11—C10 | −6.4 (2) |
O8ii—Zn2—N7—C18 | −174.29 (14) | C13—C12—C11—N4 | 1.5 (3) |
O5—Zn2—N7—C18 | 11.19 (13) | C13—C12—C11—C10 | −177.7 (2) |
N5—Zn2—N7—C18 | −71.54 (14) | C10—N3—C6—C7 | −0.6 (3) |
N7—Zn2—N5—C21 | −2.31 (19) | Zn1—N3—C6—C7 | 179.70 (18) |
N6—Zn2—N5—C21 | 179.1 (2) | C1—N1—C3—C2 | 0.1 (2) |
O8ii—Zn2—N5—C21 | 92.85 (19) | Zn1—N1—C3—C2 | 170.47 (14) |
O5—Zn2—N5—C21 | −81.61 (19) | C1—N1—C3—C4 | −175.13 (18) |
N7—Zn2—N5—C25 | 167.90 (15) | Zn1—N1—C3—C4 | −4.8 (2) |
N6—Zn2—N5—C25 | −10.66 (14) | N2—C2—C3—N1 | −0.1 (2) |
O8ii—Zn2—N5—C25 | −96.93 (15) | C5—C2—C3—N1 | −177.3 (2) |
O5—Zn2—N5—C25 | 88.60 (15) | N2—C2—C3—C4 | 174.3 (2) |
N1—Zn1—N3—C6 | −20.78 (19) | C5—C2—C3—C4 | −2.8 (4) |
N2i—Zn1—N3—C6 | 127.0 (3) | O2—C4—C3—N1 | 2.6 (3) |
N4—Zn1—N3—C6 | 176.0 (2) | O1—C4—C3—N1 | 179.75 (18) |
O3i—Zn1—N3—C6 | 80.36 (19) | O2—C4—C3—C2 | −171.3 (2) |
O2—Zn1—N3—C6 | −99.01 (19) | O1—C4—C3—C2 | 5.8 (3) |
N1—Zn1—N3—C10 | 159.51 (15) | C30—C29—C28—C27 | −1.6 (4) |
N2i—Zn1—N3—C10 | −52.7 (4) | C26—C27—C28—C29 | −0.6 (4) |
N4—Zn1—N3—C10 | −3.69 (15) | C21—N5—C25—C24 | 0.0 (3) |
O3i—Zn1—N3—C10 | −99.35 (15) | Zn2—N5—C25—C24 | −171.14 (17) |
O2—Zn1—N3—C10 | 81.28 (15) | C21—N5—C25—C26 | −176.39 (19) |
N2—C1—N1—C3 | −0.1 (2) | Zn2—N5—C25—C26 | 12.5 (2) |
N2—C1—N1—Zn1 | −165.50 (17) | C23—C24—C25—N5 | 0.5 (3) |
N2i—Zn1—N1—C1 | −100.2 (2) | C23—C24—C25—C26 | 176.6 (2) |
N4—Zn1—N1—C1 | 122.8 (3) | N6—C26—C25—N5 | −6.7 (3) |
N3—Zn1—N1—C1 | 73.4 (2) | C27—C26—C25—N5 | 169.8 (2) |
O3i—Zn1—N1—C1 | −19.6 (2) | N6—C26—C25—C24 | 176.9 (2) |
O2—Zn1—N1—C1 | 168.5 (2) | C27—C26—C25—C24 | −6.6 (3) |
N2i—Zn1—N1—C3 | 95.09 (14) | C10—C9—C8—C7 | −0.8 (3) |
N4—Zn1—N1—C3 | −41.9 (3) | N3—C6—C7—C8 | −0.1 (4) |
N3—Zn1—N1—C3 | −91.32 (14) | C9—C8—C7—C6 | 0.8 (4) |
O3i—Zn1—N1—C3 | 175.62 (13) | C6—N3—C10—C9 | 0.6 (3) |
O2—Zn1—N1—C3 | 3.76 (13) | Zn1—N3—C10—C9 | −179.70 (16) |
C29—C30—N6—C26 | 0.7 (3) | C6—N3—C10—C11 | −178.08 (19) |
C29—C30—N6—Zn2 | 177.32 (18) | Zn1—N3—C10—C11 | 1.7 (2) |
C27—C26—N6—C30 | −3.0 (3) | C8—C9—C10—N3 | 0.1 (3) |
C25—C26—N6—C30 | 173.52 (19) | C8—C9—C10—C11 | 178.7 (2) |
C27—C26—N6—Zn2 | −179.76 (17) | N4—C11—C10—N3 | 3.0 (3) |
C25—C26—N6—Zn2 | −3.2 (2) | C12—C11—C10—N3 | −177.8 (2) |
N7—Zn2—N6—C30 | −174.08 (19) | N4—C11—C10—C9 | −175.6 (2) |
N8ii—Zn2—N6—C30 | 13.41 (18) | C12—C11—C10—C9 | 3.6 (3) |
O8ii—Zn2—N6—C30 | −65.99 (17) | C25—N5—C21—C22 | −0.7 (3) |
O5—Zn2—N6—C30 | 110.43 (17) | Zn2—N5—C21—C22 | 169.15 (18) |
N5—Zn2—N6—C30 | −169.40 (18) | C15—C14—C13—C12 | −0.2 (3) |
N7—Zn2—N6—C26 | 2.6 (3) | C11—C12—C13—C14 | −0.8 (3) |
N8ii—Zn2—N6—C26 | −169.94 (16) | C25—C24—C23—C22 | −0.3 (4) |
O8ii—Zn2—N6—C26 | 110.66 (16) | C24—C23—C22—C21 | −0.4 (4) |
O5—Zn2—N6—C26 | −72.92 (16) | N5—C21—C22—C23 | 0.9 (4) |
N5—Zn2—N6—C26 | 7.25 (15) | N8—C17—C20—O8 | −3.5 (3) |
C14—C15—N4—C11 | −0.1 (3) | C18—C17—C20—O8 | 172.7 (2) |
C14—C15—N4—Zn1 | −175.14 (16) | N8—C17—C20—O7 | 176.03 (19) |
N1—Zn1—N4—C15 | 129.0 (2) | C18—C17—C20—O7 | −7.8 (4) |
N2i—Zn1—N4—C15 | −8.41 (18) | N2—C2—C5—O3 | 0.2 (3) |
N3—Zn1—N4—C15 | −179.40 (19) | C3—C2—C5—O3 | 177.1 (2) |
O3i—Zn1—N4—C15 | −87.96 (18) | N2—C2—C5—O4 | −178.63 (19) |
O2—Zn1—N4—C15 | 84.44 (18) | C3—C2—C5—O4 | −1.7 (3) |
N1—Zn1—N4—C11 | −46.1 (3) | O7—C20—O8—Zn2iii | 172.29 (18) |
N2i—Zn1—N4—C11 | 176.46 (15) | C17—C20—O8—Zn2iii | −8.3 (2) |
N3—Zn1—N4—C11 | 5.48 (15) | O4—C5—O3—Zn1iv | 170.43 (17) |
O3i—Zn1—N4—C11 | 96.92 (16) | C2—C5—O3—Zn1iv | −8.4 (2) |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2; (iv) −x, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O6 | 0.82 | 1.67 | 2.486 (2) | 180 |
O4—H4A···O1 | 0.82 | 1.67 | 2.485 (2) | 179 |
C9—H9···O5 | 0.93 | 2.57 | 3.387 (3) | 148 |
C12—H12···O5 | 0.93 | 2.48 | 3.246 (3) | 139 |
C12—H12···O6 | 0.93 | 2.50 | 3.182 (3) | 130 |
C13—H13···O8v | 0.93 | 2.45 | 3.077 (3) | 124 |
C16—H16···O7vi | 0.93 | 2.30 | 3.204 (2) | 165 |
Symmetry codes: (v) −x+1, −y+2, −z+1; (vi) x, −y+3/2, z+1/2. |