metal-organic compounds
In the title coordination polymer, [Zn(C9H6O5)(C8H12N2)]n, the ZnII atom is surrounded by two chelating 3-carboxylatophenoxyacetate (3-CPOA) dianions and one 1,10-phenanthroline (phen) ligand. Adjacent ZnII atoms are bridged by 3-CPOA to form a zigzag chain structure. The polymeric chains are connected via π–π stacking interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805035750/xu6077sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805035750/xu6077Isup2.hkl |
CCDC reference: 256885
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.
catena-Poly[[(1,10-phenanthroline-κ2N,N')zinc(II)]-µ-3-
carboxylatophenoxyacetato-κ2O,O':κ2O'',O'''] top
Crystal data top
[Zn(C9H6O5)(C8H12N2)] | F(000) = 896 |
Mr = 439.73 | Dx = 1.630 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 15325 reflections |
a = 7.6164 (15) Å | θ = 3.0–27.5° |
b = 15.542 (3) Å | µ = 1.41 mm−1 |
c = 15.186 (3) Å | T = 295 K |
β = 94.60 (3)° | Prism, colorless |
V = 1791.8 (6) Å3 | 0.37 × 0.24 × 0.19 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4085 independent reflections |
Radiation source: fine-focus sealed tube | 3241 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −20→20 |
Tmin = 0.624, Tmax = 0.775 | l = −19→19 |
17147 measured reflections |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0468P)2 + 0.3474P] where P = (Fo2 + 2Fc2)/3 |
4085 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.72774 (3) | 0.167873 (15) | 0.660579 (15) | 0.04261 (10) | |
O1 | 0.7047 (2) | 0.32590 (10) | 0.66007 (12) | 0.0569 (4) | |
O2 | 0.4961 (2) | 0.22907 (9) | 0.64081 (11) | 0.0511 (4) | |
O3 | 0.3637 (2) | 0.60832 (10) | 0.59409 (12) | 0.0644 (5) | |
O4 | 0.5511 (2) | 0.66050 (11) | 0.75065 (11) | 0.0628 (5) | |
O5 | 0.7980 (3) | 0.63536 (15) | 0.69337 (13) | 0.0806 (6) | |
N1 | 0.8197 (2) | 0.17276 (10) | 0.53422 (11) | 0.0389 (4) | |
N2 | 0.6913 (2) | 0.03875 (11) | 0.62042 (11) | 0.0403 (4) | |
C1 | 0.8804 (3) | 0.23990 (14) | 0.49221 (15) | 0.0492 (5) | |
C2 | 0.9360 (3) | 0.23427 (16) | 0.40784 (16) | 0.0579 (6) | |
C3 | 0.9261 (3) | 0.15744 (17) | 0.36500 (15) | 0.0549 (6) | |
C4 | 0.8588 (3) | 0.08464 (14) | 0.40578 (13) | 0.0430 (5) | |
C5 | 0.8403 (3) | 0.00179 (16) | 0.36500 (15) | 0.0519 (5) | |
C6 | 0.7742 (3) | −0.06482 (15) | 0.40754 (15) | 0.0516 (5) | |
C7 | 0.7216 (3) | −0.05586 (13) | 0.49553 (15) | 0.0437 (5) | |
C8 | 0.6546 (3) | −0.12345 (15) | 0.54405 (18) | 0.0555 (6) | |
C9 | 0.6115 (3) | −0.10942 (15) | 0.62797 (18) | 0.0581 (6) | |
C10 | 0.6306 (3) | −0.02705 (15) | 0.66462 (15) | 0.0501 (5) | |
C11 | 0.7384 (2) | 0.02465 (12) | 0.53764 (13) | 0.0363 (4) | |
C12 | 0.8075 (2) | 0.09603 (12) | 0.49157 (12) | 0.0355 (4) | |
C13 | 0.5474 (3) | 0.30644 (13) | 0.64579 (13) | 0.0410 (4) | |
C14 | 0.4079 (3) | 0.37551 (12) | 0.63429 (12) | 0.0373 (4) | |
C15 | 0.2313 (3) | 0.35438 (15) | 0.63704 (16) | 0.0480 (5) | |
C16 | 0.1055 (3) | 0.41841 (16) | 0.62768 (18) | 0.0602 (6) | |
C17 | 0.1536 (3) | 0.50241 (16) | 0.61370 (17) | 0.0598 (6) | |
C18 | 0.3307 (3) | 0.52352 (13) | 0.61017 (14) | 0.0466 (5) | |
C19 | 0.4584 (3) | 0.46022 (13) | 0.62220 (13) | 0.0400 (4) | |
C20 | 0.5407 (4) | 0.63428 (16) | 0.59473 (15) | 0.0620 (7) | |
C21 | 0.6348 (4) | 0.64308 (14) | 0.68622 (15) | 0.0531 (6) | |
H1 | 0.8858 | 0.2930 | 0.5206 | 0.059* | |
H2 | 0.9797 | 0.2826 | 0.3808 | 0.070* | |
H3 | 0.9640 | 0.1530 | 0.3085 | 0.066* | |
H5 | 0.8747 | −0.0059 | 0.3081 | 0.062* | |
H6 | 0.7622 | −0.1179 | 0.3794 | 0.062* | |
H8 | 0.6398 | −0.1778 | 0.5189 | 0.067* | |
H9 | 0.5694 | −0.1543 | 0.6609 | 0.070* | |
H10 | 0.5997 | −0.0181 | 0.7219 | 0.060* | |
H15 | 0.1980 | 0.2975 | 0.6451 | 0.058* | |
H16 | −0.0127 | 0.4047 | 0.6308 | 0.072* | |
H17 | 0.0679 | 0.5450 | 0.6066 | 0.072* | |
H19 | 0.5771 | 0.4744 | 0.6222 | 0.048* | |
H20A | 0.5452 | 0.6892 | 0.5647 | 0.074* | |
H20B | 0.6037 | 0.5928 | 0.5615 | 0.074* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.05203 (16) | 0.04205 (15) | 0.03411 (14) | 0.00620 (11) | 0.00573 (10) | −0.00054 (10) |
O1 | 0.0465 (9) | 0.0530 (10) | 0.0702 (12) | 0.0057 (7) | −0.0011 (8) | −0.0108 (8) |
O2 | 0.0593 (9) | 0.0323 (7) | 0.0626 (10) | 0.0038 (7) | 0.0097 (8) | −0.0003 (7) |
O3 | 0.0846 (12) | 0.0353 (8) | 0.0684 (11) | −0.0007 (8) | −0.0242 (9) | 0.0044 (7) |
O4 | 0.0806 (12) | 0.0638 (11) | 0.0429 (9) | 0.0033 (9) | −0.0024 (9) | −0.0043 (8) |
O5 | 0.0769 (13) | 0.1049 (16) | 0.0601 (12) | −0.0351 (12) | 0.0070 (10) | 0.0136 (11) |
N1 | 0.0455 (9) | 0.0360 (8) | 0.0354 (8) | 0.0007 (7) | 0.0056 (7) | 0.0011 (7) |
N2 | 0.0412 (9) | 0.0391 (9) | 0.0409 (9) | 0.0018 (7) | 0.0055 (7) | 0.0048 (7) |
C1 | 0.0579 (13) | 0.0411 (12) | 0.0495 (12) | −0.0029 (10) | 0.0092 (10) | 0.0048 (9) |
C2 | 0.0668 (15) | 0.0567 (15) | 0.0521 (14) | −0.0076 (12) | 0.0159 (12) | 0.0136 (11) |
C3 | 0.0554 (13) | 0.0740 (17) | 0.0368 (11) | −0.0017 (12) | 0.0130 (10) | 0.0064 (11) |
C4 | 0.0381 (10) | 0.0555 (13) | 0.0357 (10) | 0.0025 (9) | 0.0045 (8) | −0.0028 (9) |
C5 | 0.0471 (11) | 0.0667 (15) | 0.0420 (11) | 0.0039 (11) | 0.0043 (9) | −0.0178 (11) |
C6 | 0.0489 (12) | 0.0505 (13) | 0.0545 (13) | 0.0048 (10) | −0.0010 (10) | −0.0189 (11) |
C7 | 0.0367 (10) | 0.0387 (10) | 0.0548 (13) | 0.0025 (8) | −0.0014 (9) | −0.0033 (9) |
C8 | 0.0542 (13) | 0.0394 (12) | 0.0720 (16) | −0.0014 (10) | −0.0002 (12) | −0.0012 (11) |
C9 | 0.0579 (13) | 0.0439 (13) | 0.0721 (17) | −0.0077 (11) | 0.0024 (12) | 0.0162 (12) |
C10 | 0.0529 (12) | 0.0499 (13) | 0.0483 (12) | 0.0019 (10) | 0.0086 (10) | 0.0107 (10) |
C11 | 0.0305 (9) | 0.0384 (10) | 0.0396 (10) | 0.0036 (7) | 0.0002 (8) | −0.0007 (8) |
C12 | 0.0315 (9) | 0.0408 (10) | 0.0341 (9) | 0.0032 (8) | 0.0019 (8) | 0.0002 (8) |
C13 | 0.0532 (12) | 0.0408 (11) | 0.0294 (9) | 0.0053 (9) | 0.0061 (9) | −0.0054 (8) |
C14 | 0.0453 (10) | 0.0358 (10) | 0.0305 (9) | 0.0016 (8) | 0.0016 (8) | −0.0052 (8) |
C15 | 0.0491 (12) | 0.0403 (11) | 0.0547 (13) | −0.0041 (9) | 0.0045 (10) | −0.0082 (9) |
C16 | 0.0419 (11) | 0.0574 (14) | 0.0807 (17) | −0.0005 (11) | 0.0003 (12) | −0.0196 (13) |
C17 | 0.0526 (13) | 0.0495 (13) | 0.0742 (17) | 0.0131 (11) | −0.0141 (12) | −0.0132 (12) |
C18 | 0.0623 (13) | 0.0344 (10) | 0.0407 (11) | 0.0009 (10) | −0.0114 (10) | −0.0048 (8) |
C19 | 0.0461 (11) | 0.0396 (10) | 0.0338 (10) | −0.0032 (9) | 0.0001 (8) | −0.0031 (8) |
C20 | 0.105 (2) | 0.0408 (12) | 0.0390 (12) | −0.0176 (13) | −0.0043 (13) | 0.0074 (10) |
C21 | 0.0768 (17) | 0.0392 (11) | 0.0423 (12) | −0.0216 (11) | −0.0018 (12) | 0.0079 (9) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.4622 (17) | C5—C6 | 1.340 (3) |
Zn1—O2 | 2.0053 (16) | C5—H5 | 0.9300 |
Zn1—O4i | 2.0745 (19) | C6—C7 | 1.432 (3) |
Zn1—O5i | 2.298 (2) | C6—H6 | 0.9300 |
Zn1—N1 | 2.0962 (18) | C7—C8 | 1.403 (3) |
Zn1—N2 | 2.1093 (17) | C7—C11 | 1.406 (3) |
O1—C13 | 1.237 (3) | C8—C9 | 1.359 (4) |
O2—C13 | 1.265 (2) | C8—H8 | 0.9300 |
O4—C21 | 1.240 (3) | C9—C10 | 1.399 (3) |
O5—C21 | 1.245 (3) | C9—H9 | 0.9300 |
Zn1—C13 | 2.554 (2) | C10—H10 | 0.9300 |
Zn1—C21i | 2.503 (2) | C11—C12 | 1.434 (3) |
O3—C18 | 1.367 (3) | C13—C14 | 1.511 (3) |
O3—C20 | 1.406 (3) | C14—C19 | 1.388 (3) |
O4—Zn1ii | 2.0745 (18) | C14—C15 | 1.388 (3) |
O5—Zn1ii | 2.298 (2) | C15—C16 | 1.381 (3) |
N1—C1 | 1.325 (3) | C15—H15 | 0.9300 |
N2—C10 | 1.326 (3) | C16—C17 | 1.377 (3) |
N2—C11 | 1.352 (3) | C16—H16 | 0.9300 |
N1—C12 | 1.357 (2) | C17—C18 | 1.393 (3) |
C1—C2 | 1.384 (3) | C17—H17 | 0.9300 |
C1—H1 | 0.9300 | C18—C19 | 1.386 (3) |
C2—C3 | 1.359 (3) | C19—H19 | 0.9300 |
C2—H2 | 0.9300 | C20—C21 | 1.518 (3) |
C3—C4 | 1.406 (3) | C20—H20A | 0.9700 |
C3—H3 | 0.9300 | C20—H20B | 0.9700 |
C4—C5 | 1.431 (3) | C21—Zn1ii | 2.503 (2) |
C4—C12 | 1.401 (3) | ||
O2—Zn1—O1 | 57.64 (5) | C3—C2—C1 | 119.3 (2) |
O2—Zn1—O4i | 141.46 (7) | C3—C2—H2 | 120.4 |
O2—Zn1—O5i | 96.12 (7) | C3—C4—C5 | 124.1 (2) |
O2—Zn1—N1 | 101.55 (7) | C4—C12—C11 | 119.78 (18) |
O2—Zn1—N2 | 108.32 (6) | C4—C3—H3 | 119.9 |
O4i—Zn1—O1 | 96.38 (6) | C4—C5—H5 | 119.5 |
O4i—Zn1—O5i | 59.23 (8) | C5—C6—C7 | 121.3 (2) |
O4i—Zn1—N1 | 106.46 (7) | C5—C6—H6 | 119.4 |
O4i—Zn1—N2 | 102.50 (7) | C6—C5—C4 | 121.0 (2) |
O5i—Zn1—O1 | 102.17 (7) | C6—C5—H5 | 119.5 |
N1—Zn1—O1 | 89.43 (6) | C7—C6—H6 | 119.4 |
N1—Zn1—O5i | 162.17 (7) | C7—C8—H8 | 120.1 |
N1—Zn1—N2 | 79.38 (6) | C7—C11—C12 | 119.33 (18) |
N2—Zn1—O1 | 160.12 (6) | C8—C7—C11 | 116.8 (2) |
N2—Zn1—O5i | 92.89 (7) | C8—C7—C6 | 123.9 (2) |
O1—Zn1—C13 | 28.48 (6) | C8—C9—C10 | 119.6 (2) |
O1—Zn1—C21i | 100.42 (6) | C8—C9—H9 | 120.2 |
O1—C13—C14 | 120.57 (19) | C9—C8—C7 | 119.9 (2) |
O1—C13—O2 | 122.2 (2) | C9—C8—H8 | 120.1 |
O1—C13—Zn1 | 71.62 (12) | C9—C10—H10 | 118.9 |
O2—Zn1—C13 | 29.16 (6) | C10—N2—Zn1 | 129.07 (15) |
O2—Zn1—C21i | 120.62 (8) | C10—N2—C11 | 118.33 (18) |
O2—C13—C14 | 117.22 (19) | C10—C9—H9 | 120.2 |
O2—C13—Zn1 | 50.58 (10) | C11—N2—Zn1 | 112.60 (12) |
O3—C18—C17 | 115.2 (2) | C11—C7—C6 | 119.26 (19) |
O3—C18—C19 | 124.8 (2) | C12—N1—Zn1 | 112.96 (12) |
O3—C20—C21 | 114.5 (2) | C12—C4—C3 | 116.5 (2) |
O3—C20—H20A | 108.6 | C12—C4—C5 | 119.4 (2) |
O3—C20—H20B | 108.6 | C13—O1—Zn1 | 79.90 (12) |
O4i—Zn1—C13 | 120.43 (7) | C13—O2—Zn1 | 100.26 (13) |
O4i—Zn1—C21i | 29.58 (8) | C14—C13—Zn1 | 167.80 (15) |
O4—C21—Zn1ii | 55.68 (12) | C14—C15—H15 | 120.3 |
O4—C21—O5 | 121.7 (2) | C14—C19—H19 | 120.3 |
O4—C21—C20 | 120.5 (3) | C15—C14—C13 | 120.18 (19) |
O5i—Zn1—C13 | 100.57 (7) | C15—C16—H16 | 119.7 |
O5i—Zn1—C21i | 29.66 (8) | C16—C15—C14 | 119.5 (2) |
O5—C21—Zn1ii | 66.02 (14) | C16—C15—H15 | 120.3 |
O5—C21—C20 | 117.8 (2) | C16—C17—C18 | 120.0 (2) |
N1—Zn1—C13 | 96.07 (6) | C16—C17—H17 | 120.0 |
N1—Zn1—C21i | 135.31 (8) | C17—C16—C15 | 120.6 (2) |
N1—C1—C2 | 122.7 (2) | C17—C16—H16 | 119.7 |
N1—C1—H1 | 118.6 | C18—O3—C20 | 117.73 (19) |
N1—C12—C11 | 117.43 (17) | C18—C17—H17 | 120.0 |
N1—C12—C4 | 122.78 (18) | C18—C19—C14 | 119.44 (19) |
N2—Zn1—C13 | 136.01 (7) | C18—C19—H19 | 120.3 |
N2—Zn1—C21i | 99.08 (7) | C19—C14—C13 | 119.28 (18) |
N2—C10—C9 | 122.3 (2) | C19—C14—C15 | 120.54 (19) |
N2—C10—H10 | 118.9 | C19—C18—C17 | 120.0 (2) |
N2—C11—C12 | 117.60 (17) | C20—C21—Zn1ii | 175.1 (2) |
N2—C11—C7 | 123.07 (18) | C21i—Zn1—C13 | 113.16 (7) |
C1—N1—Zn1 | 128.62 (14) | C21—O4—Zn1ii | 94.74 (16) |
C1—N1—C12 | 118.38 (18) | C21—O5—Zn1ii | 84.32 (16) |
C1—C2—H2 | 120.4 | C21—C20—H20A | 108.6 |
C2—C1—H1 | 118.6 | C21—C20—H20B | 108.6 |
C2—C3—C4 | 120.3 (2) | H20A—C20—H20B | 107.6 |
C2—C3—H3 | 119.9 | ||
O2—Zn1—O1—C13 | −0.20 (12) | C6—C7—C11—N2 | 179.77 (18) |
O4i—Zn1—O1—C13 | −149.61 (13) | C8—C7—C11—C12 | 179.47 (18) |
N1—Zn1—O1—C13 | 103.89 (13) | C6—C7—C11—C12 | 0.1 (3) |
N2—Zn1—O1—C13 | 48.6 (2) | C1—N1—C12—C4 | 1.0 (3) |
O5i—Zn1—O1—C13 | −89.77 (13) | Zn1—N1—C12—C4 | 179.02 (14) |
C21i—Zn1—O1—C13 | −119.98 (14) | C1—N1—C12—C11 | −178.83 (18) |
O4i—Zn1—O2—C13 | 54.44 (17) | Zn1—N1—C12—C11 | −0.8 (2) |
N1—Zn1—O2—C13 | −81.67 (13) | C3—C4—C12—N1 | 0.4 (3) |
N2—Zn1—O2—C13 | −164.17 (12) | C5—C4—C12—N1 | −179.41 (18) |
O5i—Zn1—O2—C13 | 100.73 (14) | C3—C4—C12—C11 | −179.73 (18) |
O1—Zn1—O2—C13 | 0.19 (12) | C5—C4—C12—C11 | 0.4 (3) |
C21i—Zn1—O2—C13 | 82.94 (15) | N2—C11—C12—N1 | −0.4 (2) |
O2—Zn1—N1—C1 | 72.21 (19) | C7—C11—C12—N1 | 179.28 (16) |
O4i—Zn1—N1—C1 | −81.02 (19) | N2—C11—C12—C4 | 179.73 (16) |
N2—Zn1—N1—C1 | 179.0 (2) | C7—C11—C12—C4 | −0.6 (3) |
O5i—Zn1—N1—C1 | −115.6 (3) | Zn1—O1—C13—O2 | 0.31 (19) |
O1—Zn1—N1—C1 | 15.47 (19) | Zn1—O1—C13—C14 | 179.78 (18) |
C21i—Zn1—N1—C1 | −88.8 (2) | Zn1—O2—C13—O1 | −0.4 (2) |
C13—Zn1—N1—C1 | 43.21 (19) | Zn1—O2—C13—C14 | −179.86 (14) |
O2—Zn1—N1—C12 | −105.55 (13) | O2—Zn1—C13—O1 | 179.7 (2) |
O4i—Zn1—N1—C12 | 101.22 (14) | O4i—Zn1—C13—O1 | 35.67 (15) |
N2—Zn1—N1—C12 | 1.19 (13) | N1—Zn1—C13—O1 | −77.47 (13) |
O5i—Zn1—N1—C12 | 66.6 (3) | N2—Zn1—C13—O1 | −158.45 (12) |
O1—Zn1—N1—C12 | −162.29 (13) | O5i—Zn1—C13—O1 | 96.07 (13) |
C21i—Zn1—N1—C12 | 93.40 (16) | C21i—Zn1—C13—O1 | 67.92 (15) |
C13—Zn1—N1—C12 | −134.55 (14) | O4i—Zn1—C13—O2 | −143.99 (13) |
O2—Zn1—N2—C10 | −82.61 (19) | N1—Zn1—C13—O2 | 102.87 (14) |
O4i—Zn1—N2—C10 | 73.92 (19) | N2—Zn1—C13—O2 | 21.90 (17) |
N1—Zn1—N2—C10 | 178.62 (19) | O5i—Zn1—C13—O2 | −83.59 (14) |
O5i—Zn1—N2—C10 | 14.82 (19) | O1—Zn1—C13—O2 | −179.7 (2) |
O1—Zn1—N2—C10 | −124.7 (2) | C21i—Zn1—C13—O2 | −111.74 (14) |
C21i—Zn1—N2—C10 | 44.00 (19) | O2—Zn1—C13—C14 | 0.6 (6) |
C13—Zn1—N2—C10 | −93.64 (19) | O4i—Zn1—C13—C14 | −143.4 (6) |
O2—Zn1—N2—C11 | 97.36 (13) | N1—Zn1—C13—C14 | 103.4 (6) |
O4i—Zn1—N2—C11 | −106.11 (13) | N2—Zn1—C13—C14 | 22.5 (7) |
N1—Zn1—N2—C11 | −1.41 (12) | O5i—Zn1—C13—C14 | −83.0 (6) |
O5i—Zn1—N2—C11 | −165.21 (13) | C21i—Zn1—C13—C14 | −111.2 (6) |
O1—Zn1—N2—C11 | 55.3 (2) | O1—C13—C14—C19 | 12.8 (3) |
C21i—Zn1—N2—C11 | −136.03 (14) | O2—C13—C14—C19 | −167.70 (18) |
C13—Zn1—N2—C11 | 86.33 (15) | Zn1—C13—C14—C19 | −168.2 (5) |
C12—N1—C1—C2 | −1.8 (3) | O1—C13—C14—C15 | −166.3 (2) |
Zn1—N1—C1—C2 | −179.44 (17) | O2—C13—C14—C15 | 13.2 (3) |
N1—C1—C2—C3 | 1.1 (4) | Zn1—C13—C14—C15 | 12.7 (7) |
C1—C2—C3—C4 | 0.5 (4) | C19—C14—C15—C16 | 0.0 (3) |
C2—C3—C4—C12 | −1.1 (3) | C13—C14—C15—C16 | 179.1 (2) |
C2—C3—C4—C5 | 178.7 (2) | C14—C15—C16—C17 | 1.5 (4) |
C12—C4—C5—C6 | 0.2 (3) | C15—C16—C17—C18 | −0.9 (4) |
C3—C4—C5—C6 | −179.6 (2) | C20—O3—C18—C19 | −3.8 (3) |
C4—C5—C6—C7 | −0.7 (3) | C20—O3—C18—C17 | 176.5 (2) |
C5—C6—C7—C8 | −178.8 (2) | C16—C17—C18—O3 | 178.6 (2) |
C5—C6—C7—C11 | 0.6 (3) | C16—C17—C18—C19 | −1.1 (4) |
C11—C7—C8—C9 | −0.7 (3) | O3—C18—C19—C14 | −177.19 (19) |
C6—C7—C8—C9 | 178.6 (2) | C17—C18—C19—C14 | 2.5 (3) |
C7—C8—C9—C10 | 1.4 (3) | C15—C14—C19—C18 | −1.9 (3) |
C11—N2—C10—C9 | −1.0 (3) | C13—C14—C19—C18 | 178.94 (17) |
Zn1—N2—C10—C9 | 178.96 (16) | C18—O3—C20—C21 | −76.4 (3) |
C8—C9—C10—N2 | −0.5 (4) | Zn1ii—O4—C21—O5 | 0.9 (2) |
C10—N2—C11—C7 | 1.7 (3) | Zn1ii—O4—C21—C20 | −176.41 (18) |
Zn1—N2—C11—C7 | −178.27 (14) | Zn1ii—O5—C21—O4 | −0.8 (2) |
C10—N2—C11—C12 | −178.60 (17) | Zn1ii—O5—C21—C20 | 176.56 (18) |
Zn1—N2—C11—C12 | 1.4 (2) | O3—C20—C21—O4 | −27.6 (3) |
C8—C7—C11—N2 | −0.8 (3) | O3—C20—C21—O5 | 155.0 (2) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2. |