The hydrothermal synthesis of the novel complex poly[aqua(μ
4-benzene-1,2,3-tricarboxylato)[μ
2-4,4′-(hydrazine-1,2-diylidenedimethanylylidene)dipyridine](μ
3-hydroxido)dizinc(II)], [Zn(C
9H
3O
6)(OH)(C
12H
10N
4)(H
2O)]
n, is described. The benzene-1,2,3-tricarboxylate ligand connects neighbouring Zn
4(OH)
2 secondary building units (SBUs) producing an infinite one-dimensional chain. Adjacent one-dimensional chains are connected by the
N,
N′-bis[(pyridin-4-yl)methylidene]hydrazine ligand, forming a two-dimensional layered structure. Adjacent layers are stacked to generate a three-dimensional supramolecular architecture
via O—H
O hydrogen-bond interactions. The thermal stability of this complex is described and the complex also appears to have potential for application as a luminescent material.
Supporting information
CCDC reference: 1404590
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).
Poly[aqua(µ
4-benzene-1,2,3-tricarboxylato)[µ
2-4,4'-(hydrazine-1,2-diylidenedimethanylylidene)dipyridine](µ
3-hydroxido)dizinc(II)]
top
Crystal data top
[Zn(C9H3O6)(OH)(C12H10N4)(H2O)] | Z = 2 |
Mr = 583.12 | F(000) = 588 |
Triclinic, P1 | Dx = 1.883 Mg m−3 |
a = 7.622 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.341 (5) Å | Cell parameters from 2998 reflections |
c = 13.682 (5) Å | θ = 2.5–26.9° |
α = 85.003 (5)° | µ = 2.39 mm−1 |
β = 86.125 (5)° | T = 296 K |
γ = 73.369 (5)° | Block, yellow |
V = 1028.3 (9) Å3 | 0.42 × 0.40 × 0.39 mm |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 3722 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −9→9 |
Tmin = 0.380, Tmax = 0.391 | k = −13→13 |
9072 measured reflections | l = −17→17 |
4626 independent reflections | |
Refinement top
Refinement on F2 | 4 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0368P)2 + 0.5201P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
4626 reflections | Δρmax = 0.37 e Å−3 |
325 parameters | Δρmin = −0.48 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.63751 (4) | 0.58432 (3) | 0.64682 (2) | 0.02088 (10) | |
Zn2 | 1.03098 (4) | 0.35465 (3) | 0.55486 (2) | 0.01913 (10) | |
C1 | 1.1068 (4) | 0.6246 (3) | 0.77462 (19) | 0.0187 (5) | |
C2 | 1.2140 (3) | 0.6921 (3) | 0.71484 (19) | 0.0163 (5) | |
C3 | 1.3020 (4) | 0.7745 (3) | 0.7559 (2) | 0.0195 (6) | |
C4 | 1.2830 (4) | 0.7870 (3) | 0.8574 (2) | 0.0263 (6) | |
H4 | 1.3396 | 0.8426 | 0.8853 | 0.032* | |
C5 | 1.1810 (4) | 0.7173 (3) | 0.9166 (2) | 0.0276 (7) | |
H5 | 1.1725 | 0.7242 | 0.9842 | 0.033* | |
C6 | 1.0905 (4) | 0.6367 (3) | 0.8755 (2) | 0.0254 (6) | |
H6 | 1.0199 | 0.5915 | 0.9153 | 0.030* | |
C7 | 1.0046 (4) | 0.5419 (3) | 0.72820 (19) | 0.0199 (6) | |
C8 | 1.2228 (4) | 0.6759 (3) | 0.60577 (19) | 0.0179 (5) | |
C9 | 1.4106 (4) | 0.8543 (3) | 0.6914 (2) | 0.0231 (6) | |
C10 | 0.9521 (4) | 0.2051 (3) | 0.7515 (2) | 0.0251 (6) | |
H10 | 0.9927 | 0.2707 | 0.7780 | 0.030* | |
C11 | 0.9019 (4) | 0.1092 (3) | 0.8146 (2) | 0.0264 (6) | |
H11 | 0.9098 | 0.1104 | 0.8821 | 0.032* | |
C12 | 0.8394 (4) | 0.0104 (3) | 0.7769 (2) | 0.0232 (6) | |
C13 | 0.8410 (4) | 0.0086 (3) | 0.6755 (2) | 0.0289 (7) | |
H13 | 0.8071 | −0.0588 | 0.6473 | 0.035* | |
C14 | 0.8938 (4) | 0.1082 (3) | 0.6167 (2) | 0.0291 (7) | |
H14 | 0.8940 | 0.1060 | 0.5489 | 0.035* | |
C15 | 0.7682 (4) | −0.0867 (3) | 0.8403 (2) | 0.0283 (7) | |
H15 | 0.7415 | −0.1580 | 0.8133 | 0.034* | |
C16 | 0.5015 (4) | −0.3423 (3) | 1.2988 (2) | 0.0233 (6) | |
H16 | 0.4969 | −0.3363 | 1.3664 | 0.028* | |
C17 | 0.5647 (4) | −0.2494 (3) | 1.2381 (2) | 0.0249 (6) | |
H17 | 0.5983 | −0.1808 | 1.2647 | 0.030* | |
C18 | 0.5775 (4) | −0.2594 (3) | 1.1373 (2) | 0.0236 (6) | |
C19 | 0.5200 (4) | −0.3615 (3) | 1.0999 (2) | 0.0246 (6) | |
H19 | 0.5272 | −0.3713 | 1.0327 | 0.029* | |
C20 | 0.4525 (4) | −0.4471 (3) | 1.1648 (2) | 0.0236 (6) | |
H20 | 0.4091 | −0.5122 | 1.1397 | 0.028* | |
C21 | 0.6507 (4) | −0.1640 (3) | 1.0725 (2) | 0.0293 (7) | |
H21 | 0.6825 | −0.0948 | 1.0995 | 0.035* | |
N1 | 0.9451 (3) | 0.2083 (2) | 0.65323 (17) | 0.0223 (5) | |
N2 | 0.4465 (3) | −0.4408 (2) | 1.26337 (17) | 0.0195 (5) | |
N3 | 0.7430 (4) | −0.0734 (3) | 0.93223 (19) | 0.0318 (6) | |
N4 | 0.6711 (4) | −0.1743 (3) | 0.9805 (2) | 0.0330 (6) | |
O1 | 0.8355 (3) | 0.5712 (2) | 0.74854 (15) | 0.0334 (5) | |
O2 | 1.0957 (3) | 0.45242 (19) | 0.67359 (14) | 0.0236 (4) | |
O3 | 1.0706 (3) | 0.71388 (19) | 0.56567 (13) | 0.0219 (4) | |
O4 | 1.3761 (3) | 0.6224 (2) | 0.56373 (14) | 0.0255 (4) | |
O5 | 1.5563 (3) | 0.7863 (2) | 0.64737 (16) | 0.0292 (5) | |
O6 | 1.3551 (3) | 0.9786 (2) | 0.68665 (19) | 0.0409 (6) | |
O7 | 1.2856 (3) | 0.1934 (2) | 0.54335 (17) | 0.0366 (6) | |
H7A | 1.343 (5) | 0.178 (4) | 0.4881 (16) | 0.055* | |
H7B | 1.308 (5) | 0.120 (3) | 0.579 (2) | 0.055* | |
O8 | 0.8107 (3) | 0.53254 (19) | 0.53524 (13) | 0.0187 (4) | |
H8 | 0.741 (4) | 0.515 (3) | 0.499 (2) | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02107 (18) | 0.02041 (18) | 0.02181 (18) | −0.00839 (13) | 0.00552 (13) | −0.00141 (13) |
Zn2 | 0.02181 (18) | 0.01772 (17) | 0.01803 (17) | −0.00666 (13) | −0.00012 (13) | 0.00087 (12) |
C1 | 0.0168 (13) | 0.0202 (14) | 0.0189 (13) | −0.0051 (11) | −0.0001 (10) | −0.0017 (10) |
C2 | 0.0161 (13) | 0.0157 (13) | 0.0167 (13) | −0.0035 (10) | −0.0004 (10) | −0.0018 (10) |
C3 | 0.0176 (13) | 0.0184 (13) | 0.0229 (14) | −0.0052 (11) | −0.0008 (11) | −0.0032 (11) |
C4 | 0.0284 (16) | 0.0276 (15) | 0.0260 (15) | −0.0103 (13) | −0.0025 (12) | −0.0100 (12) |
C5 | 0.0258 (16) | 0.0392 (18) | 0.0179 (14) | −0.0079 (13) | −0.0018 (12) | −0.0065 (12) |
C6 | 0.0231 (15) | 0.0302 (16) | 0.0226 (15) | −0.0082 (13) | 0.0027 (12) | −0.0007 (12) |
C7 | 0.0206 (14) | 0.0236 (14) | 0.0172 (13) | −0.0104 (11) | −0.0023 (11) | 0.0046 (11) |
C8 | 0.0220 (14) | 0.0134 (12) | 0.0204 (13) | −0.0086 (11) | −0.0019 (11) | 0.0002 (10) |
C9 | 0.0254 (15) | 0.0199 (14) | 0.0257 (15) | −0.0089 (12) | −0.0019 (12) | −0.0024 (11) |
C10 | 0.0279 (16) | 0.0270 (15) | 0.0233 (15) | −0.0134 (13) | 0.0000 (12) | 0.0001 (12) |
C11 | 0.0315 (17) | 0.0294 (16) | 0.0175 (14) | −0.0089 (13) | 0.0017 (12) | 0.0009 (12) |
C12 | 0.0216 (15) | 0.0196 (14) | 0.0262 (15) | −0.0047 (11) | 0.0025 (12) | 0.0039 (11) |
C13 | 0.0387 (18) | 0.0230 (15) | 0.0281 (16) | −0.0147 (13) | 0.0025 (13) | −0.0011 (12) |
C14 | 0.0432 (19) | 0.0270 (16) | 0.0202 (15) | −0.0159 (14) | 0.0047 (13) | −0.0027 (12) |
C15 | 0.0274 (16) | 0.0235 (15) | 0.0343 (17) | −0.0102 (13) | 0.0017 (13) | 0.0046 (13) |
C16 | 0.0225 (15) | 0.0256 (15) | 0.0215 (14) | −0.0065 (12) | −0.0038 (11) | 0.0009 (11) |
C17 | 0.0303 (16) | 0.0222 (15) | 0.0236 (15) | −0.0096 (12) | −0.0040 (12) | 0.0007 (11) |
C18 | 0.0213 (14) | 0.0216 (14) | 0.0269 (15) | −0.0064 (12) | −0.0006 (12) | 0.0048 (12) |
C19 | 0.0279 (16) | 0.0293 (16) | 0.0171 (14) | −0.0100 (13) | 0.0005 (12) | 0.0008 (11) |
C20 | 0.0272 (15) | 0.0238 (15) | 0.0213 (14) | −0.0097 (12) | 0.0000 (12) | −0.0020 (11) |
C21 | 0.0299 (17) | 0.0265 (16) | 0.0336 (18) | −0.0133 (13) | 0.0005 (14) | 0.0037 (13) |
N1 | 0.0248 (13) | 0.0197 (12) | 0.0221 (12) | −0.0075 (10) | 0.0014 (10) | 0.0020 (9) |
N2 | 0.0171 (11) | 0.0214 (12) | 0.0199 (12) | −0.0069 (9) | −0.0006 (9) | 0.0028 (9) |
N3 | 0.0365 (16) | 0.0317 (15) | 0.0295 (14) | −0.0180 (12) | 0.0075 (12) | 0.0066 (11) |
N4 | 0.0379 (16) | 0.0312 (15) | 0.0320 (15) | −0.0173 (12) | 0.0058 (12) | 0.0066 (12) |
O1 | 0.0226 (11) | 0.0560 (15) | 0.0277 (11) | −0.0205 (11) | 0.0047 (9) | −0.0098 (10) |
O2 | 0.0272 (11) | 0.0199 (10) | 0.0248 (10) | −0.0077 (8) | −0.0058 (8) | 0.0000 (8) |
O3 | 0.0242 (10) | 0.0215 (10) | 0.0198 (10) | −0.0056 (8) | −0.0054 (8) | 0.0004 (8) |
O4 | 0.0228 (11) | 0.0332 (12) | 0.0214 (10) | −0.0097 (9) | 0.0023 (8) | −0.0034 (9) |
O5 | 0.0288 (12) | 0.0225 (11) | 0.0378 (12) | −0.0120 (9) | 0.0113 (10) | −0.0049 (9) |
O6 | 0.0452 (15) | 0.0181 (11) | 0.0573 (16) | −0.0090 (10) | 0.0087 (12) | 0.0007 (10) |
O7 | 0.0362 (14) | 0.0320 (13) | 0.0318 (13) | 0.0005 (11) | 0.0094 (10) | 0.0076 (10) |
O8 | 0.0170 (10) | 0.0212 (10) | 0.0192 (10) | −0.0072 (8) | −0.0010 (8) | −0.0026 (8) |
Geometric parameters (Å, º) top
Zn1—O8 | 1.956 (2) | C11—C12 | 1.394 (4) |
Zn1—O5i | 2.002 (2) | C11—H11 | 0.9300 |
Zn1—N2ii | 2.060 (2) | C12—C13 | 1.388 (4) |
Zn1—O1 | 2.089 (2) | C12—C15 | 1.466 (4) |
Zn1—O4i | 2.279 (2) | C13—C14 | 1.385 (4) |
Zn2—O8 | 2.117 (2) | C13—H13 | 0.9300 |
Zn2—O3iii | 2.1241 (19) | C14—N1 | 1.349 (4) |
Zn2—O2 | 2.141 (2) | C14—H14 | 0.9300 |
Zn2—N1 | 2.150 (2) | C15—N3 | 1.273 (4) |
Zn2—O8iii | 2.166 (2) | C15—H15 | 0.9300 |
Zn2—O7 | 2.174 (2) | C16—N2 | 1.344 (4) |
C1—C6 | 1.390 (4) | C16—C17 | 1.384 (4) |
C1—C2 | 1.401 (4) | C16—H16 | 0.9300 |
C1—C7 | 1.511 (4) | C17—C18 | 1.386 (4) |
C2—C3 | 1.398 (4) | C17—H17 | 0.9300 |
C2—C8 | 1.511 (4) | C18—C19 | 1.399 (4) |
C3—C4 | 1.399 (4) | C18—C21 | 1.472 (4) |
C3—C9 | 1.520 (4) | C19—C20 | 1.378 (4) |
C4—C5 | 1.384 (4) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—N2 | 1.353 (4) |
C5—C6 | 1.396 (4) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—N4 | 1.268 (4) |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
C7—O1 | 1.255 (3) | N2—Zn1ii | 2.060 (2) |
C7—O2 | 1.257 (3) | N3—N4 | 1.408 (3) |
C8—O3 | 1.260 (3) | O3—Zn2iii | 2.1242 (19) |
C8—O4 | 1.264 (3) | O4—Zn1iv | 2.279 (2) |
C9—O6 | 1.230 (3) | O5—Zn1iv | 2.002 (2) |
C9—O5 | 1.275 (3) | O7—H7A | 0.852 (18) |
C10—N1 | 1.347 (4) | O7—H7B | 0.843 (17) |
C10—C11 | 1.378 (4) | O8—Zn2iii | 2.166 (2) |
C10—H10 | 0.9300 | O8—H8 | 0.812 (18) |
| | | |
O8—Zn1—O5i | 109.03 (8) | C10—C11—C12 | 119.6 (3) |
O8—Zn1—N2ii | 120.97 (9) | C10—C11—H11 | 120.2 |
O5i—Zn1—N2ii | 129.87 (9) | C12—C11—H11 | 120.2 |
O8—Zn1—O1 | 95.91 (9) | C13—C12—C11 | 117.6 (3) |
O5i—Zn1—O1 | 91.16 (9) | C13—C12—C15 | 120.1 (3) |
N2ii—Zn1—O1 | 87.35 (9) | C11—C12—C15 | 122.3 (3) |
O8—Zn1—O4i | 97.04 (8) | C14—C13—C12 | 119.3 (3) |
O5i—Zn1—O4i | 82.10 (8) | C14—C13—H13 | 120.3 |
N2ii—Zn1—O4i | 88.28 (8) | C12—C13—H13 | 120.3 |
O1—Zn1—O4i | 166.77 (8) | N1—C14—C13 | 123.1 (3) |
O8—Zn2—O3iii | 85.85 (8) | N1—C14—H14 | 118.4 |
O8—Zn2—O2 | 84.78 (8) | C13—C14—H14 | 118.4 |
O3iii—Zn2—O2 | 170.62 (7) | N3—C15—C12 | 120.0 (3) |
O8—Zn2—N1 | 109.95 (9) | N3—C15—H15 | 120.0 |
O3iii—Zn2—N1 | 90.44 (9) | C12—C15—H15 | 120.0 |
O2—Zn2—N1 | 92.40 (9) | N2—C16—C17 | 122.2 (3) |
O8—Zn2—O8iii | 84.76 (9) | N2—C16—H16 | 118.9 |
O3iii—Zn2—O8iii | 94.90 (8) | C17—C16—H16 | 118.9 |
O2—Zn2—O8iii | 84.63 (8) | C16—C17—C18 | 119.6 (3) |
N1—Zn2—O8iii | 164.72 (8) | C16—C17—H17 | 120.2 |
O8—Zn2—O7 | 165.98 (8) | C18—C17—H17 | 120.2 |
O3iii—Zn2—O7 | 90.55 (9) | C17—C18—C19 | 118.4 (3) |
O2—Zn2—O7 | 98.65 (9) | C17—C18—C21 | 119.9 (3) |
N1—Zn2—O7 | 83.59 (10) | C19—C18—C21 | 121.6 (3) |
O8iii—Zn2—O7 | 82.05 (9) | C20—C19—C18 | 118.6 (3) |
C6—C1—C2 | 120.2 (2) | C20—C19—H19 | 120.7 |
C6—C1—C7 | 120.4 (2) | C18—C19—H19 | 120.7 |
C2—C1—C7 | 119.4 (2) | N2—C20—C19 | 123.0 (3) |
C3—C2—C1 | 120.2 (2) | N2—C20—H20 | 118.5 |
C3—C2—C8 | 122.6 (2) | C19—C20—H20 | 118.5 |
C1—C2—C8 | 117.2 (2) | N4—C21—C18 | 121.3 (3) |
C2—C3—C4 | 119.1 (3) | N4—C21—H21 | 119.4 |
C2—C3—C9 | 120.8 (2) | C18—C21—H21 | 119.4 |
C4—C3—C9 | 120.1 (2) | C10—N1—C14 | 117.1 (2) |
C5—C4—C3 | 120.6 (3) | C10—N1—Zn2 | 122.89 (19) |
C5—C4—H4 | 119.7 | C14—N1—Zn2 | 119.84 (19) |
C3—C4—H4 | 119.7 | C16—N2—C20 | 118.0 (2) |
C4—C5—C6 | 120.4 (3) | C16—N2—Zn1ii | 122.57 (19) |
C4—C5—H5 | 119.8 | C20—N2—Zn1ii | 119.38 (18) |
C6—C5—H5 | 119.8 | C15—N3—N4 | 111.8 (3) |
C1—C6—C5 | 119.5 (3) | C21—N4—N3 | 112.1 (3) |
C1—C6—H6 | 120.2 | C7—O1—Zn1 | 124.31 (19) |
C5—C6—H6 | 120.2 | C7—O2—Zn2 | 134.37 (18) |
O1—C7—O2 | 126.9 (3) | C8—O3—Zn2iii | 132.50 (18) |
O1—C7—C1 | 115.6 (2) | C8—O4—Zn1iv | 119.59 (17) |
O2—C7—C1 | 117.5 (2) | C9—O5—Zn1iv | 124.78 (18) |
O3—C8—O4 | 125.9 (2) | Zn2—O7—H7A | 121 (3) |
O3—C8—C2 | 115.2 (2) | Zn2—O7—H7B | 124 (3) |
O4—C8—C2 | 118.9 (2) | H7A—O7—H7B | 108 (2) |
O6—C9—O5 | 124.7 (3) | Zn1—O8—Zn2 | 117.66 (9) |
O6—C9—C3 | 118.4 (3) | Zn1—O8—Zn2iii | 130.91 (10) |
O5—C9—C3 | 116.9 (2) | Zn2—O8—Zn2iii | 95.24 (9) |
N1—C10—C11 | 123.1 (3) | Zn1—O8—H8 | 98 (2) |
N1—C10—H10 | 118.5 | Zn2—O8—H8 | 107 (2) |
C11—C10—H10 | 118.5 | Zn2iii—O8—H8 | 107 (2) |
| | | |
C6—C1—C2—C3 | −1.4 (4) | C13—C12—C15—N3 | −170.3 (3) |
C7—C1—C2—C3 | 176.8 (2) | C11—C12—C15—N3 | 7.8 (5) |
C6—C1—C2—C8 | −179.1 (2) | N2—C16—C17—C18 | −1.9 (4) |
C7—C1—C2—C8 | −0.9 (4) | C16—C17—C18—C19 | 2.0 (4) |
C1—C2—C3—C4 | 0.8 (4) | C16—C17—C18—C21 | −177.9 (3) |
C8—C2—C3—C4 | 178.3 (3) | C17—C18—C19—C20 | 0.3 (4) |
C1—C2—C3—C9 | −176.8 (2) | C21—C18—C19—C20 | −179.8 (3) |
C8—C2—C3—C9 | 0.7 (4) | C18—C19—C20—N2 | −2.9 (4) |
C2—C3—C4—C5 | 0.9 (4) | C17—C18—C21—N4 | 177.0 (3) |
C9—C3—C4—C5 | 178.5 (3) | C19—C18—C21—N4 | −2.9 (5) |
C3—C4—C5—C6 | −2.0 (5) | C11—C10—N1—C14 | −3.0 (4) |
C2—C1—C6—C5 | 0.4 (4) | C11—C10—N1—Zn2 | −178.1 (2) |
C7—C1—C6—C5 | −177.8 (3) | C13—C14—N1—C10 | 3.2 (5) |
C4—C5—C6—C1 | 1.3 (4) | C13—C14—N1—Zn2 | 178.4 (2) |
C6—C1—C7—O1 | 52.7 (4) | C17—C16—N2—C20 | −0.6 (4) |
C2—C1—C7—O1 | −125.5 (3) | C17—C16—N2—Zn1ii | 177.4 (2) |
C6—C1—C7—O2 | −127.6 (3) | C19—C20—N2—C16 | 3.1 (4) |
C2—C1—C7—O2 | 54.2 (4) | C19—C20—N2—Zn1ii | −175.0 (2) |
C3—C2—C8—O3 | −118.8 (3) | C12—C15—N3—N4 | 178.9 (3) |
C1—C2—C8—O3 | 58.8 (3) | C18—C21—N4—N3 | −179.9 (3) |
C3—C2—C8—O4 | 63.8 (4) | C15—N3—N4—C21 | 178.1 (3) |
C1—C2—C8—O4 | −118.6 (3) | O2—C7—O1—Zn1 | −41.7 (4) |
C2—C3—C9—O6 | 114.5 (3) | C1—C7—O1—Zn1 | 138.0 (2) |
C4—C3—C9—O6 | −63.0 (4) | O1—C7—O2—Zn2 | 24.3 (4) |
C2—C3—C9—O5 | −66.9 (4) | C1—C7—O2—Zn2 | −155.38 (19) |
C4—C3—C9—O5 | 115.6 (3) | O4—C8—O3—Zn2iii | 29.2 (4) |
N1—C10—C11—C12 | −0.5 (5) | C2—C8—O3—Zn2iii | −147.99 (18) |
C10—C11—C12—C13 | 3.8 (4) | O3—C8—O4—Zn1iv | 172.92 (19) |
C10—C11—C12—C15 | −174.3 (3) | C2—C8—O4—Zn1iv | −9.9 (3) |
C11—C12—C13—C14 | −3.7 (5) | O6—C9—O5—Zn1iv | −175.2 (2) |
C15—C12—C13—C14 | 174.5 (3) | C3—C9—O5—Zn1iv | 6.2 (3) |
C12—C13—C14—N1 | 0.2 (5) | | |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+2; (iii) −x+2, −y+1, −z+1; (iv) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7B···O6v | 0.84 (2) | 1.96 (2) | 2.787 (3) | 167 (4) |
O8—H8···O4iii | 0.81 (2) | 2.15 (2) | 2.894 (3) | 153 (3) |
O7—H7A···O5vi | 0.85 (2) | 2.00 (2) | 2.816 (3) | 159 (3) |
Symmetry codes: (iii) −x+2, −y+1, −z+1; (v) x, y−1, z; (vi) −x+3, −y+1, −z+1. |