In the coordination polymer, poly[[{μ-1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole-κ2N:N′}(μ-5-carboxybenzene-1,3-dicarboxylato-κ2O1:O3)zinc(II)] dimethylformamide monosolvate pentahydrate], {[Zn(C9H4O6)(C11H10N4)]·C3H7NO·5H2O}n, the ZnII ion is coordinated by two N atoms from two symmetry-related 1-[(1H-benzimidazol-2-yl)methyl]-1H-imidazole (bmi) ligands and two O atoms from two symmetry-related 5-carboxybenzene-1,3-dicarboxylate (Hbtc2−) ligands in a slightly distorted tetrahedral geometry. The ZnII ions are bridged by Hbtc2− and bmi ligands, leading to a 4-connected two-dimensional network with the topological notation (44.62). Adjacent layers are further connected by 12 kinds of hydrogen bonds and also by π–π interactions, resulting in a three-dimensional supramolecular architecture in the solid state.
Supporting information
CCDC reference: 1411859
Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear (Rigaku/MSC, 2004); data reduction: CrystalClear (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (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[[{µ-1-[(1
H-benzimidazol-2-yl)methyl]-1
H-imidazole-
κ2N:
N'}(µ-5-carboxybenzene-1,3-dicarboxylato-
κ2O1:
O3)zinc(II)]
dimethylformamide monosolvate pentahydrate]
top
Crystal data top
[Zn(C9H4O6)(C11H10N4)]·C3H7NO·5H2O | F(000) = 1320 |
Mr = 634.90 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.174 (2) Å | Cell parameters from 7004 reflections |
b = 20.843 (4) Å | θ = 2.0–27.9° |
c = 13.274 (3) Å | µ = 0.96 mm−1 |
β = 100.40 (3)° | T = 293 K |
V = 2768.5 (10) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.18 × 0.15 mm |
Data collection top
Rigaku Saturn diffractometer | 6614 independent reflections |
Radiation source: fine-focus sealed tube | 5902 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.048 |
ω scans | θmax = 27.9°, θmin = 2.3° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004) | h = −13→13 |
Tmin = 0.949, Tmax = 1.000 | k = −27→27 |
34313 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0763P)2 + 1.8118P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.003 |
6614 reflections | Δρmax = 0.41 e Å−3 |
373 parameters | Δρmin = −0.37 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 1.07235 (3) | 0.60660 (2) | 0.68989 (3) | 0.02833 (12) | |
N1 | 1.1158 (2) | 0.60116 (11) | 0.84423 (19) | 0.0286 (5) | |
N2 | 1.1473 (3) | 0.61848 (13) | 1.0112 (2) | 0.0355 (6) | |
H2 | 1.1558 | 0.6390 | 1.0682 | 0.043* | |
N3 | 1.0556 (3) | 0.74820 (12) | 0.9787 (2) | 0.0346 (6) | |
N4 | 1.0384 (3) | 0.81465 (12) | 1.1025 (2) | 0.0324 (5) | |
N5 | 0.4823 (3) | 0.13705 (17) | 0.4534 (3) | 0.0559 (8) | |
O1 | 0.9114 (2) | 0.55000 (12) | 0.64959 (18) | 0.0411 (5) | |
O2 | 0.8204 (2) | 0.62607 (12) | 0.72955 (19) | 0.0429 (6) | |
O3 | 0.3301 (2) | 0.63177 (12) | 0.7006 (2) | 0.0464 (6) | |
O4 | 0.2070 (2) | 0.54813 (11) | 0.64463 (17) | 0.0354 (5) | |
O5 | 0.6453 (3) | 0.34656 (14) | 0.5641 (3) | 0.0833 (11) | |
O6 | 0.4273 (3) | 0.35112 (12) | 0.5598 (3) | 0.0601 (7) | |
H6 | 0.4327 | 0.3123 | 0.5516 | 0.090* | |
O7 | 0.4351 (4) | 0.22582 (15) | 0.5377 (3) | 0.0793 (10) | |
O8 | 1.1509 (4) | 0.66041 (17) | 1.2043 (2) | 0.0782 (10) | |
H8A | 1.0962 | 0.6712 | 1.2428 | 0.117* | |
H8B | 1.2213 | 0.6797 | 1.2330 | 0.117* | |
O9 | 0.7054 (4) | 0.73851 (18) | 0.7731 (3) | 0.0890 (11) | |
H9A | 0.7413 | 0.7036 | 0.7592 | 0.133* | |
H9B | 0.6525 | 0.7383 | 0.8159 | 0.133* | |
O10 | 0.9151 (4) | 0.83381 (18) | 0.7832 (3) | 0.0928 (12) | |
H10A | 0.8402 | 0.8145 | 0.7723 | 0.139* | |
H10B | 0.9146 | 0.8626 | 0.8285 | 0.139* | |
O11 | 0.0622 (5) | 0.43012 (17) | 0.5722 (3) | 0.1145 (16) | |
H11A | 0.0981 | 0.4159 | 0.5236 | 0.172* | |
H11B | 0.1009 | 0.4658 | 0.5884 | 0.172* | |
O12 | 0.3806 (7) | 0.7541 (2) | 0.7612 (4) | 0.159 (2) | |
H12A | 0.3869 | 0.7244 | 0.7186 | 0.238* | |
H12B | 0.4042 | 0.7361 | 0.8191 | 0.238* | |
C1 | 0.8126 (3) | 0.57484 (16) | 0.6822 (2) | 0.0335 (7) | |
C2 | 0.3197 (3) | 0.57634 (15) | 0.6678 (2) | 0.0303 (6) | |
C3 | 0.5475 (4) | 0.37631 (17) | 0.5752 (3) | 0.0431 (8) | |
C4 | 0.6820 (3) | 0.53927 (15) | 0.6601 (2) | 0.0314 (6) | |
C5 | 0.5654 (3) | 0.57057 (15) | 0.6740 (2) | 0.0304 (6) | |
H5 | 0.5701 | 0.6128 | 0.6970 | 0.037* | |
C6 | 0.4425 (3) | 0.53979 (14) | 0.6541 (2) | 0.0294 (6) | |
C7 | 0.4359 (3) | 0.47635 (15) | 0.6218 (2) | 0.0309 (6) | |
H7 | 0.3541 | 0.4553 | 0.6086 | 0.037* | |
C8 | 0.5517 (3) | 0.44437 (15) | 0.6092 (2) | 0.0331 (6) | |
C9 | 0.6740 (3) | 0.47614 (16) | 0.6271 (2) | 0.0341 (7) | |
H9 | 0.7508 | 0.4548 | 0.6169 | 0.041* | |
C10 | 1.1174 (3) | 0.79304 (14) | 1.0416 (2) | 0.0331 (6) | |
H10 | 1.2043 | 0.8072 | 1.0424 | 0.040* | |
C11 | 0.9194 (3) | 0.78199 (16) | 1.0754 (3) | 0.0401 (7) | |
H11 | 0.8441 | 0.7875 | 1.1052 | 0.048* | |
C12 | 0.9295 (3) | 0.74102 (17) | 0.9994 (3) | 0.0434 (8) | |
H12 | 0.8637 | 0.7132 | 0.9670 | 0.052* | |
C13 | 1.1099 (4) | 0.71509 (16) | 0.8981 (3) | 0.0444 (8) | |
H13A | 1.1971 | 0.7327 | 0.8943 | 0.053* | |
H13B | 1.0518 | 0.7226 | 0.8327 | 0.053* | |
C14 | 1.1227 (3) | 0.64466 (15) | 0.9170 (2) | 0.0318 (6) | |
C15 | 1.1563 (3) | 0.55305 (15) | 1.0003 (2) | 0.0320 (6) | |
C16 | 1.1767 (3) | 0.50346 (16) | 1.0715 (3) | 0.0400 (7) | |
H16 | 1.1881 | 0.5114 | 1.1415 | 0.048* | |
C17 | 1.1791 (3) | 0.44216 (17) | 1.0334 (3) | 0.0440 (8) | |
H17 | 1.1938 | 0.4077 | 1.0786 | 0.053* | |
C18 | 1.1598 (4) | 0.43062 (16) | 0.9278 (3) | 0.0430 (8) | |
H18 | 1.1612 | 0.3885 | 0.9048 | 0.052* | |
C19 | 1.1388 (3) | 0.47969 (15) | 0.8570 (2) | 0.0364 (7) | |
H19 | 1.1261 | 0.4716 | 0.7870 | 0.044* | |
C20 | 1.1376 (3) | 0.54189 (14) | 0.8950 (2) | 0.0303 (6) | |
C21 | 0.5163 (5) | 0.0996 (2) | 0.5460 (4) | 0.0647 (12) | |
H21A | 0.5297 | 0.1276 | 0.6043 | 0.097* | |
H21B | 0.5968 | 0.0759 | 0.5444 | 0.097* | |
H21C | 0.4449 | 0.0702 | 0.5509 | 0.097* | |
C22 | 0.4857 (6) | 0.1059 (3) | 0.3560 (4) | 0.0800 (15) | |
H22A | 0.4551 | 0.1353 | 0.3011 | 0.120* | |
H22B | 0.4286 | 0.0689 | 0.3490 | 0.120* | |
H22C | 0.5755 | 0.0929 | 0.3534 | 0.120* | |
C23 | 0.4459 (5) | 0.1972 (2) | 0.4572 (4) | 0.0676 (12) | |
H23A | 0.4269 | 0.2199 | 0.3960 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.02631 (19) | 0.0293 (2) | 0.0303 (2) | 0.00328 (13) | 0.00752 (14) | 0.00236 (13) |
N1 | 0.0296 (12) | 0.0287 (12) | 0.0285 (12) | 0.0023 (10) | 0.0079 (10) | −0.0008 (9) |
N2 | 0.0418 (15) | 0.0366 (14) | 0.0283 (13) | −0.0025 (11) | 0.0069 (11) | −0.0046 (10) |
N3 | 0.0412 (15) | 0.0290 (13) | 0.0346 (13) | −0.0026 (11) | 0.0098 (11) | −0.0047 (10) |
N4 | 0.0326 (13) | 0.0285 (12) | 0.0377 (13) | −0.0024 (10) | 0.0102 (11) | −0.0050 (10) |
N5 | 0.055 (2) | 0.053 (2) | 0.057 (2) | 0.0034 (16) | 0.0023 (16) | −0.0126 (16) |
O1 | 0.0230 (10) | 0.0531 (14) | 0.0481 (13) | −0.0020 (10) | 0.0090 (10) | −0.0027 (11) |
O2 | 0.0312 (12) | 0.0418 (13) | 0.0559 (15) | −0.0034 (10) | 0.0086 (11) | 0.0001 (11) |
O3 | 0.0379 (13) | 0.0365 (13) | 0.0644 (16) | 0.0032 (10) | 0.0086 (11) | −0.0096 (12) |
O4 | 0.0238 (10) | 0.0386 (12) | 0.0454 (12) | 0.0008 (9) | 0.0107 (9) | −0.0061 (10) |
O5 | 0.0624 (19) | 0.0472 (17) | 0.153 (3) | 0.0073 (14) | 0.052 (2) | −0.0183 (19) |
O6 | 0.0517 (16) | 0.0362 (14) | 0.091 (2) | −0.0029 (12) | 0.0089 (15) | −0.0116 (14) |
O7 | 0.110 (3) | 0.0486 (17) | 0.079 (2) | 0.0015 (17) | 0.016 (2) | −0.0165 (16) |
O8 | 0.100 (3) | 0.086 (2) | 0.0456 (16) | 0.004 (2) | 0.0061 (16) | −0.0180 (16) |
O9 | 0.096 (3) | 0.081 (2) | 0.091 (3) | 0.020 (2) | 0.018 (2) | −0.020 (2) |
O10 | 0.136 (4) | 0.075 (2) | 0.075 (2) | 0.006 (2) | 0.039 (2) | 0.0075 (19) |
O11 | 0.217 (5) | 0.052 (2) | 0.069 (2) | −0.007 (3) | 0.013 (3) | −0.0136 (17) |
O12 | 0.249 (7) | 0.069 (3) | 0.138 (4) | −0.022 (4) | −0.019 (4) | −0.021 (3) |
C1 | 0.0242 (14) | 0.0406 (18) | 0.0358 (16) | −0.0004 (12) | 0.0062 (12) | 0.0091 (13) |
C2 | 0.0240 (14) | 0.0351 (16) | 0.0331 (15) | 0.0026 (12) | 0.0083 (12) | 0.0021 (12) |
C3 | 0.046 (2) | 0.0395 (18) | 0.048 (2) | 0.0048 (15) | 0.0188 (16) | 0.0031 (15) |
C4 | 0.0244 (14) | 0.0390 (16) | 0.0316 (15) | 0.0010 (12) | 0.0071 (12) | 0.0042 (12) |
C5 | 0.0257 (14) | 0.0332 (15) | 0.0325 (15) | −0.0005 (12) | 0.0056 (12) | 0.0020 (12) |
C6 | 0.0221 (13) | 0.0342 (15) | 0.0322 (15) | 0.0001 (11) | 0.0061 (11) | 0.0022 (12) |
C7 | 0.0238 (14) | 0.0345 (15) | 0.0353 (15) | −0.0014 (12) | 0.0074 (12) | 0.0014 (12) |
C8 | 0.0332 (15) | 0.0333 (16) | 0.0347 (15) | 0.0039 (12) | 0.0113 (13) | 0.0043 (12) |
C9 | 0.0279 (14) | 0.0410 (17) | 0.0351 (16) | 0.0068 (13) | 0.0101 (13) | 0.0053 (13) |
C10 | 0.0342 (15) | 0.0287 (15) | 0.0372 (16) | −0.0034 (12) | 0.0085 (13) | −0.0033 (12) |
C11 | 0.0324 (16) | 0.0399 (18) | 0.0496 (19) | −0.0067 (14) | 0.0119 (14) | −0.0108 (15) |
C12 | 0.0388 (18) | 0.0410 (18) | 0.050 (2) | −0.0109 (15) | 0.0072 (15) | −0.0112 (15) |
C13 | 0.065 (2) | 0.0342 (17) | 0.0383 (18) | 0.0012 (16) | 0.0208 (17) | −0.0040 (14) |
C14 | 0.0347 (16) | 0.0336 (16) | 0.0284 (14) | 0.0014 (12) | 0.0089 (12) | −0.0009 (12) |
C15 | 0.0294 (15) | 0.0341 (16) | 0.0330 (15) | 0.0004 (12) | 0.0067 (12) | −0.0008 (12) |
C16 | 0.0413 (18) | 0.0439 (19) | 0.0346 (16) | 0.0022 (15) | 0.0063 (14) | 0.0096 (14) |
C17 | 0.0444 (19) | 0.0393 (18) | 0.048 (2) | 0.0079 (15) | 0.0090 (16) | 0.0135 (15) |
C18 | 0.0476 (19) | 0.0332 (17) | 0.049 (2) | 0.0052 (15) | 0.0122 (16) | 0.0046 (15) |
C19 | 0.0404 (17) | 0.0356 (16) | 0.0338 (16) | 0.0012 (14) | 0.0086 (13) | −0.0031 (13) |
C20 | 0.0293 (14) | 0.0312 (15) | 0.0312 (15) | 0.0024 (12) | 0.0076 (12) | 0.0023 (12) |
C21 | 0.053 (2) | 0.060 (3) | 0.079 (3) | 0.006 (2) | 0.005 (2) | 0.000 (2) |
C22 | 0.083 (4) | 0.091 (4) | 0.065 (3) | 0.013 (3) | 0.011 (3) | −0.026 (3) |
C23 | 0.080 (3) | 0.054 (3) | 0.067 (3) | 0.002 (2) | 0.008 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
Zn1—N4i | 2.003 (2) | C1—C4 | 1.503 (4) |
Zn1—O4ii | 2.005 (2) | C2—C6 | 1.503 (4) |
Zn1—O1 | 2.011 (2) | C3—C8 | 1.487 (5) |
Zn1—N1 | 2.020 (3) | C4—C9 | 1.384 (4) |
N1—C14 | 1.317 (4) | C4—C5 | 1.396 (4) |
N1—C20 | 1.406 (4) | C5—C6 | 1.387 (4) |
N2—C14 | 1.346 (4) | C5—H5 | 0.9300 |
N2—C15 | 1.376 (4) | C6—C7 | 1.388 (4) |
N2—H2 | 0.8600 | C7—C8 | 1.390 (4) |
N3—C10 | 1.333 (4) | C7—H7 | 0.9300 |
N3—C12 | 1.368 (4) | C8—C9 | 1.391 (4) |
N3—C13 | 1.463 (4) | C9—H9 | 0.9300 |
N4—C10 | 1.318 (4) | C10—H10 | 0.9300 |
N4—C11 | 1.379 (4) | C11—C12 | 1.341 (5) |
N4—Zn1iii | 2.003 (2) | C11—H11 | 0.9300 |
N5—C23 | 1.310 (6) | C12—H12 | 0.9300 |
N5—C21 | 1.445 (6) | C13—C14 | 1.491 (4) |
N5—C22 | 1.453 (5) | C13—H13A | 0.9700 |
O1—C1 | 1.274 (4) | C13—H13B | 0.9700 |
O2—C1 | 1.235 (4) | C15—C16 | 1.390 (4) |
O3—C2 | 1.233 (4) | C15—C20 | 1.395 (4) |
O4—C2 | 1.275 (4) | C16—C17 | 1.376 (5) |
O4—Zn1iv | 2.005 (2) | C16—H16 | 0.9300 |
O5—C3 | 1.203 (4) | C17—C18 | 1.400 (5) |
O6—C3 | 1.313 (4) | C17—H17 | 0.9300 |
O6—H6 | 0.8200 | C18—C19 | 1.380 (5) |
O7—C23 | 1.246 (5) | C18—H18 | 0.9300 |
O8—H8A | 0.8500 | C19—C20 | 1.392 (4) |
O8—H8B | 0.8499 | C19—H19 | 0.9300 |
O9—H9A | 0.8499 | C21—H21A | 0.9600 |
O9—H9B | 0.8500 | C21—H21B | 0.9600 |
O10—H10A | 0.8500 | C21—H21C | 0.9600 |
O10—H10B | 0.8501 | C22—H22A | 0.9600 |
O11—H11A | 0.8499 | C22—H22B | 0.9600 |
O11—H11B | 0.8501 | C22—H22C | 0.9600 |
O12—H12A | 0.8500 | C23—H23A | 0.9300 |
O12—H12B | 0.8499 | | |
| | | |
N4i—Zn1—O4ii | 112.35 (10) | C4—C9—H9 | 119.8 |
N4i—Zn1—O1 | 106.23 (11) | C8—C9—H9 | 119.8 |
O4ii—Zn1—O1 | 97.55 (9) | N4—C10—N3 | 110.7 (3) |
N4i—Zn1—N1 | 128.06 (10) | N4—C10—H10 | 124.7 |
O4ii—Zn1—N1 | 103.50 (10) | N3—C10—H10 | 124.7 |
O1—Zn1—N1 | 104.82 (10) | C12—C11—N4 | 109.1 (3) |
C14—N1—C20 | 105.7 (2) | C12—C11—H11 | 125.4 |
C14—N1—Zn1 | 132.7 (2) | N4—C11—H11 | 125.4 |
C20—N1—Zn1 | 121.51 (19) | C11—C12—N3 | 106.5 (3) |
C14—N2—C15 | 108.0 (3) | C11—C12—H12 | 126.8 |
C14—N2—H2 | 126.0 | N3—C12—H12 | 126.8 |
C15—N2—H2 | 126.0 | N3—C13—C14 | 112.0 (3) |
C10—N3—C12 | 107.7 (3) | N3—C13—H13A | 109.2 |
C10—N3—C13 | 126.3 (3) | C14—C13—H13A | 109.2 |
C12—N3—C13 | 125.9 (3) | N3—C13—H13B | 109.2 |
C10—N4—C11 | 106.0 (3) | C14—C13—H13B | 109.2 |
C10—N4—Zn1iii | 125.1 (2) | H13A—C13—H13B | 107.9 |
C11—N4—Zn1iii | 127.4 (2) | N1—C14—N2 | 112.2 (3) |
C23—N5—C21 | 120.7 (4) | N1—C14—C13 | 124.2 (3) |
C23—N5—C22 | 120.9 (4) | N2—C14—C13 | 123.5 (3) |
C21—N5—C22 | 118.4 (4) | N2—C15—C16 | 132.1 (3) |
C1—O1—Zn1 | 109.0 (2) | N2—C15—C20 | 105.7 (3) |
C2—O4—Zn1iv | 106.30 (19) | C16—C15—C20 | 122.2 (3) |
C3—O6—H6 | 109.5 | C17—C16—C15 | 116.8 (3) |
H8A—O8—H8B | 101.2 | C17—C16—H16 | 121.6 |
H9A—O9—H9B | 119.3 | C15—C16—H16 | 121.6 |
H10A—O10—H10B | 109.5 | C16—C17—C18 | 121.2 (3) |
H11A—O11—H11B | 104.7 | C16—C17—H17 | 119.4 |
H12A—O12—H12B | 103.6 | C18—C17—H17 | 119.4 |
O2—C1—O1 | 122.8 (3) | C19—C18—C17 | 122.1 (3) |
O2—C1—C4 | 120.0 (3) | C19—C18—H18 | 118.9 |
O1—C1—C4 | 117.2 (3) | C17—C18—H18 | 118.9 |
O3—C2—O4 | 122.2 (3) | C18—C19—C20 | 117.0 (3) |
O3—C2—C6 | 119.9 (3) | C18—C19—H19 | 121.5 |
O4—C2—C6 | 117.9 (3) | C20—C19—H19 | 121.5 |
O5—C3—O6 | 122.8 (4) | C19—C20—C15 | 120.7 (3) |
O5—C3—C8 | 123.4 (3) | C19—C20—N1 | 130.9 (3) |
O6—C3—C8 | 113.8 (3) | C15—C20—N1 | 108.4 (3) |
C9—C4—C5 | 118.9 (3) | N5—C21—H21A | 109.5 |
C9—C4—C1 | 122.0 (3) | N5—C21—H21B | 109.5 |
C5—C4—C1 | 119.1 (3) | H21A—C21—H21B | 109.5 |
C6—C5—C4 | 121.1 (3) | N5—C21—H21C | 109.5 |
C6—C5—H5 | 119.4 | H21A—C21—H21C | 109.5 |
C4—C5—H5 | 119.4 | H21B—C21—H21C | 109.5 |
C5—C6—C7 | 119.4 (3) | N5—C22—H22A | 109.5 |
C5—C6—C2 | 118.9 (3) | N5—C22—H22B | 109.5 |
C7—C6—C2 | 121.7 (3) | H22A—C22—H22B | 109.5 |
C8—C7—C6 | 119.9 (3) | N5—C22—H22C | 109.5 |
C8—C7—H7 | 120.0 | H22A—C22—H22C | 109.5 |
C6—C7—H7 | 120.0 | H22B—C22—H22C | 109.5 |
C7—C8—C9 | 120.2 (3) | O7—C23—N5 | 124.1 (5) |
C7—C8—C3 | 121.0 (3) | O7—C23—H23A | 118.0 |
C9—C8—C3 | 118.8 (3) | N5—C23—H23A | 118.0 |
C4—C9—C8 | 120.4 (3) | | |
| | | |
Zn1—O1—C1—O2 | 0.7 (4) | Zn1iii—N4—C11—C12 | 166.6 (2) |
Zn1—O1—C1—C4 | −179.7 (2) | N4—C11—C12—N3 | −0.1 (4) |
Zn1iv—O4—C2—O3 | −7.2 (4) | C10—N3—C12—C11 | −0.4 (4) |
Zn1iv—O4—C2—C6 | 172.7 (2) | C13—N3—C12—C11 | −177.2 (3) |
O2—C1—C4—C9 | −166.1 (3) | C10—N3—C13—C14 | 117.6 (4) |
O1—C1—C4—C9 | 14.3 (4) | C12—N3—C13—C14 | −66.1 (4) |
O2—C1—C4—C5 | 13.4 (4) | C20—N1—C14—N2 | 0.0 (3) |
O1—C1—C4—C5 | −166.2 (3) | Zn1—N1—C14—N2 | 175.9 (2) |
C9—C4—C5—C6 | −0.9 (4) | C20—N1—C14—C13 | 177.9 (3) |
C1—C4—C5—C6 | 179.6 (3) | Zn1—N1—C14—C13 | −6.2 (5) |
C4—C5—C6—C7 | 1.4 (4) | C15—N2—C14—N1 | −0.5 (4) |
C4—C5—C6—C2 | −178.4 (3) | C15—N2—C14—C13 | −178.4 (3) |
O3—C2—C6—C5 | −3.2 (4) | N3—C13—C14—N1 | 151.5 (3) |
O4—C2—C6—C5 | 176.9 (3) | N3—C13—C14—N2 | −30.9 (5) |
O3—C2—C6—C7 | 177.0 (3) | C14—N2—C15—C16 | −178.1 (3) |
O4—C2—C6—C7 | −2.9 (4) | C14—N2—C15—C20 | 0.8 (3) |
C5—C6—C7—C8 | −0.4 (4) | N2—C15—C16—C17 | 179.4 (3) |
C2—C6—C7—C8 | 179.4 (3) | C20—C15—C16—C17 | 0.7 (5) |
C6—C7—C8—C9 | −1.1 (5) | C15—C16—C17—C18 | −0.9 (5) |
C6—C7—C8—C3 | 179.7 (3) | C16—C17—C18—C19 | 0.6 (6) |
O5—C3—C8—C7 | −179.3 (4) | C17—C18—C19—C20 | 0.0 (5) |
O6—C3—C8—C7 | −0.4 (5) | C18—C19—C20—C15 | −0.3 (5) |
O5—C3—C8—C9 | 1.5 (5) | C18—C19—C20—N1 | −178.2 (3) |
O6—C3—C8—C9 | −179.6 (3) | N2—C15—C20—C19 | −179.0 (3) |
C5—C4—C9—C8 | −0.6 (4) | C16—C15—C20—C19 | 0.0 (5) |
C1—C4—C9—C8 | 178.9 (3) | N2—C15—C20—N1 | −0.7 (3) |
C7—C8—C9—C4 | 1.6 (5) | C16—C15—C20—N1 | 178.3 (3) |
C3—C8—C9—C4 | −179.2 (3) | C14—N1—C20—C19 | 178.5 (3) |
C11—N4—C10—N3 | −0.7 (4) | Zn1—N1—C20—C19 | 2.0 (4) |
Zn1iii—N4—C10—N3 | −167.3 (2) | C14—N1—C20—C15 | 0.5 (3) |
C12—N3—C10—N4 | 0.7 (4) | Zn1—N1—C20—C15 | −176.02 (19) |
C13—N3—C10—N4 | 177.6 (3) | C21—N5—C23—O7 | −1.5 (7) |
C10—N4—C11—C12 | 0.5 (4) | C22—N5—C23—O7 | 176.7 (5) |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x, −y+3/2, z+1/2; (iv) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O8 | 0.86 | 1.87 | 2.702 (4) | 162 |
O6—H6···O7 | 0.82 | 1.81 | 2.631 (4) | 176 |
O9—H9A···O2 | 0.85 | 1.88 | 2.728 (4) | 180 |
O10—H10A···O9 | 0.85 | 2.10 | 2.900 (6) | 157 |
O11—H11B···O4 | 0.85 | 2.09 | 2.938 (4) | 173 |
O12—H12A···O3 | 0.85 | 2.02 | 2.696 (5) | 136 |
O8—H8A···O10iii | 0.85 | 2.01 | 2.788 (5) | 151 |
O8—H8B···O12v | 0.85 | 2.11 | 2.927 (7) | 161 |
O9—H9B···O7vi | 0.85 | 2.29 | 3.117 (5) | 163 |
O10—H10B···O11vi | 0.85 | 1.91 | 2.757 (5) | 172 |
O12—H12B···O7vi | 0.85 | 2.28 | 3.030 (7) | 147 |
O11—H11A···O1vii | 0.85 | 2.39 | 3.033 (5) | 133 |
Symmetry codes: (iii) x, −y+3/2, z+1/2; (v) x+1, −y+3/2, z+1/2; (vi) −x+1, y+1/2, −z+3/2; (vii) −x+1, −y+1, −z+1. |