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The rational selection of ligands is vitally important in the construction of coordination complexes. Two novel ZnII complexes, namely bis(acetato-κO)bis[1-(1H-benzotriazol-1-ylmethyl)-2-propyl-1H-imidazole-κN3]zinc(II) monohydrate, [Zn(C13H15N5)2(C2H3O2)2]·H2O, (1), and bis(azido-κN1)bis[1-(1H-benzotriazol-1-ylmethyl)-2-propyl-1H-imidazole-κN3]zinc(II), [Zn(C13H15N5)2(N3)2], (2), constructed from the asymmetric multidentate imidazole ligand, have been synthesized under mild conditions and characterized by elemental analyses, IR spectroscopy and single-crystal X-ray diffraction analysis. Both complexes exhibit a three-dimensional supramolecular network directed by different intermolecular interactions between discrete mononuclear units. The complexes were also investigated by fluorescence and thermal analyses. The experimental results show that (1) is a promising fluorescence sensor for detecting Fe3+ ions and (2) is effective as an accelerator of the thermal decomposition of ammonium perchlorate.
Supporting information
CCDC references: 1588302; 1588301
For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: CrysAlis PRO (Agilent, 2013). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015) for (1); SHELXL2013 (Sheldrick, 2008) for (2). For both structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Bis(acetato-
κO)bis[1-(1
H-benzotriazol-1-ylmethyl)-2-propyl-1
H-imidazole-
κN3]zinc(II) monohydrate (1)
top
Crystal data top
[Zn(C13H15N5)2(C2H3O2)2]·H2O | Z = 2 |
Mr = 684.07 | F(000) = 716 |
Triclinic, P1 | Dx = 1.405 Mg m−3 |
a = 8.7481 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.9399 (4) Å | Cell parameters from 7610 reflections |
c = 16.4168 (7) Å | θ = 5.0–70.5° |
α = 84.921 (3)° | µ = 1.52 mm−1 |
β = 88.623 (3)° | T = 293 K |
γ = 71.161 (3)° | 0.27 × 0.20 × 0.14 mm |
V = 1616.52 (10) Å3 | |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5664 independent reflections |
Mirror monochromator | 5308 reflections with I > 2σ(I) |
Detector resolution: 15.9737 pixels mm-1 | Rint = 0.019 |
ω scans | θmax = 67.1°, θmin = 5.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −10→9 |
Tmin = 0.608, Tmax = 1.000 | k = −13→14 |
11919 measured reflections | l = −19→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.4511P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
5664 reflections | Δρmax = 0.29 e Å−3 |
428 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | |
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 | Occ. (<1) |
Zn1 | 1.02757 (3) | −0.00682 (2) | 0.25322 (2) | 0.03908 (9) | |
O1 | 0.95723 (16) | −0.14326 (11) | 0.28933 (8) | 0.0500 (3) | |
O2 | 1.0568 (2) | −0.21872 (14) | 0.17489 (9) | 0.0740 (4) | |
O3 | 1.25782 (16) | −0.04755 (14) | 0.22652 (8) | 0.0583 (3) | |
O4 | 1.3228 (2) | −0.0966 (2) | 0.35545 (11) | 0.0970 (7) | |
N1 | 0.93810 (16) | 0.08175 (11) | 0.14324 (8) | 0.0384 (3) | |
N2 | 0.81844 (17) | 0.12726 (12) | 0.02321 (8) | 0.0417 (3) | |
N3 | 0.5575 (2) | 0.21495 (14) | −0.04498 (10) | 0.0517 (4) | |
N4 | 0.4274 (2) | 0.18206 (18) | −0.02071 (12) | 0.0676 (5) | |
N5 | 0.2985 (2) | 0.2753 (2) | −0.02800 (14) | 0.0766 (6) | |
N6 | 0.95185 (16) | 0.08900 (12) | 0.35073 (8) | 0.0393 (3) | |
N7 | 0.94527 (17) | 0.19330 (12) | 0.45456 (8) | 0.0428 (3) | |
N8 | 0.8640 (2) | 0.38876 (13) | 0.50373 (9) | 0.0491 (4) | |
N9 | 0.8794 (2) | 0.47218 (16) | 0.44502 (11) | 0.0613 (4) | |
N10 | 0.7687 (2) | 0.57207 (16) | 0.45548 (13) | 0.0686 (5) | |
C1 | 0.5775 (3) | 0.1504 (3) | 0.24849 (15) | 0.0760 (7) | |
H1A | 0.664124 | 0.183514 | 0.243072 | 0.114* | |
H1B | 0.608344 | 0.081100 | 0.286584 | 0.114* | |
H1C | 0.482889 | 0.208163 | 0.268077 | 0.114* | |
C2 | 0.5420 (2) | 0.11704 (19) | 0.16708 (12) | 0.0547 (5) | |
H2A | 0.507146 | 0.188045 | 0.129546 | 0.066* | |
H2B | 0.453544 | 0.084629 | 0.172987 | 0.066* | |
C3 | 0.6874 (2) | 0.02579 (16) | 0.13014 (12) | 0.0486 (4) | |
H3A | 0.733707 | −0.039366 | 0.171231 | 0.058* | |
H3B | 0.650328 | −0.006163 | 0.085035 | 0.058* | |
C4 | 0.8147 (2) | 0.07605 (13) | 0.10024 (10) | 0.0381 (3) | |
C5 | 1.0226 (2) | 0.13863 (15) | 0.09145 (11) | 0.0428 (4) | |
H5 | 1.115022 | 0.154878 | 0.105735 | 0.051* | |
C6 | 0.9511 (2) | 0.16673 (15) | 0.01766 (11) | 0.0461 (4) | |
H6 | 0.983973 | 0.204936 | −0.027930 | 0.055* | |
C7 | 0.7167 (2) | 0.12707 (17) | −0.04604 (11) | 0.0537 (5) | |
H7A | 0.770353 | 0.141581 | −0.096339 | 0.064* | |
H7B | 0.705049 | 0.048980 | −0.046061 | 0.064* | |
C8 | 0.5097 (2) | 0.33359 (17) | −0.07007 (11) | 0.0511 (4) | |
C9 | 0.5916 (3) | 0.40954 (19) | −0.10200 (13) | 0.0614 (5) | |
H9 | 0.702674 | 0.383535 | −0.110254 | 0.074* | |
C10 | 0.4980 (3) | 0.5257 (2) | −0.12063 (16) | 0.0752 (7) | |
H10 | 0.547747 | 0.579720 | −0.142206 | 0.090* | |
C11 | 0.3329 (4) | 0.5653 (2) | −0.10856 (17) | 0.0812 (7) | |
H11 | 0.275452 | 0.644977 | −0.121873 | 0.097* | |
C12 | 0.2524 (3) | 0.4914 (2) | −0.07792 (17) | 0.0807 (8) | |
H12 | 0.141257 | 0.518782 | −0.070160 | 0.097* | |
C13 | 0.3439 (3) | 0.3710 (2) | −0.05816 (13) | 0.0617 (5) | |
C14 | 1.1475 (3) | 0.3641 (2) | 0.21491 (15) | 0.0709 (6) | |
H14A | 1.088347 | 0.428639 | 0.177022 | 0.106* | |
H14B | 1.214284 | 0.300401 | 0.185270 | 0.106* | |
H14C | 1.214075 | 0.390765 | 0.249010 | 0.106* | |
C15 | 1.0301 (3) | 0.32062 (18) | 0.26768 (13) | 0.0569 (5) | |
H15A | 0.966668 | 0.290042 | 0.233392 | 0.068* | |
H15B | 0.956711 | 0.386722 | 0.293940 | 0.068* | |
C16 | 1.1186 (2) | 0.22276 (17) | 0.33334 (12) | 0.0511 (4) | |
H16A | 1.201570 | 0.161469 | 0.307428 | 0.061* | |
H16B | 1.171332 | 0.256238 | 0.371417 | 0.061* | |
C17 | 1.0083 (2) | 0.16814 (14) | 0.37936 (10) | 0.0405 (3) | |
C18 | 0.8495 (2) | 0.06328 (15) | 0.40943 (10) | 0.0417 (4) | |
H18 | 0.792747 | 0.010252 | 0.405226 | 0.050* | |
C19 | 0.8449 (2) | 0.12661 (15) | 0.47331 (10) | 0.0447 (4) | |
H19 | 0.785483 | 0.125739 | 0.520979 | 0.054* | |
C20 | 0.9816 (2) | 0.27071 (16) | 0.50929 (12) | 0.0536 (5) | |
H20A | 0.985075 | 0.235556 | 0.565078 | 0.064* | |
H20B | 1.087553 | 0.276719 | 0.496311 | 0.064* | |
C21 | 0.7390 (2) | 0.43804 (16) | 0.55381 (11) | 0.0475 (4) | |
C22 | 0.6787 (3) | 0.55602 (17) | 0.52184 (14) | 0.0575 (5) | |
C23 | 0.5467 (3) | 0.6358 (2) | 0.5584 (2) | 0.0803 (8) | |
H23 | 0.505844 | 0.714934 | 0.537855 | 0.096* | |
C24 | 0.4807 (3) | 0.5938 (3) | 0.6245 (2) | 0.0887 (9) | |
H24 | 0.392401 | 0.644827 | 0.649675 | 0.106* | |
C25 | 0.5424 (3) | 0.4749 (3) | 0.65591 (16) | 0.0820 (7) | |
H25 | 0.493501 | 0.449617 | 0.701608 | 0.098* | |
C26 | 0.6724 (3) | 0.3939 (2) | 0.62204 (13) | 0.0643 (5) | |
H26 | 0.712850 | 0.315125 | 0.643269 | 0.077* | |
C27 | 0.9908 (2) | −0.22528 (15) | 0.24068 (10) | 0.0427 (4) | |
C28 | 0.9446 (3) | −0.33296 (17) | 0.26824 (15) | 0.0616 (5) | |
H28A | 1.039652 | −0.397358 | 0.285411 | 0.092* | |
H28B | 0.893957 | −0.354933 | 0.223826 | 0.092* | |
H28C | 0.870777 | −0.315607 | 0.313140 | 0.092* | |
C29 | 1.3552 (2) | −0.10071 (17) | 0.28346 (13) | 0.0540 (5) | |
C30 | 1.5235 (3) | −0.1721 (2) | 0.2597 (2) | 0.0843 (8) | |
H30A | 1.537643 | −0.255254 | 0.270081 | 0.126* | |
H30B | 1.600717 | −0.152308 | 0.291165 | 0.126* | |
H30C | 1.539411 | −0.154303 | 0.202526 | 0.126* | |
O1WA | 0.6070 (7) | −0.1409 (6) | 0.4459 (4) | 0.131 (2) | 0.5 |
H1WA | 0.516878 | −0.107067 | 0.421676 | 0.196* | 0.5 |
H1WB | 0.682098 | −0.126907 | 0.417275 | 0.196* | 0.5 |
O1WB | 0.5611 (12) | −0.0619 (8) | 0.4788 (7) | 0.221 (5) | 0.5 |
H1WC | 0.461603 | −0.039164 | 0.465847 | 0.331* | 0.5 |
H1WD | 0.585933 | −0.003344 | 0.493237 | 0.331* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.04335 (14) | 0.04085 (13) | 0.03331 (13) | −0.01424 (10) | 0.00541 (9) | −0.00347 (9) |
O1 | 0.0648 (8) | 0.0437 (6) | 0.0449 (7) | −0.0220 (6) | 0.0107 (6) | −0.0074 (5) |
O2 | 0.1017 (12) | 0.0711 (10) | 0.0494 (8) | −0.0289 (9) | 0.0241 (8) | −0.0095 (7) |
O3 | 0.0442 (7) | 0.0783 (9) | 0.0516 (8) | −0.0188 (7) | 0.0055 (6) | −0.0060 (7) |
O4 | 0.0811 (12) | 0.1187 (15) | 0.0575 (10) | 0.0068 (11) | 0.0093 (9) | 0.0185 (10) |
N1 | 0.0419 (7) | 0.0363 (7) | 0.0363 (7) | −0.0125 (6) | 0.0042 (6) | −0.0016 (5) |
N2 | 0.0453 (7) | 0.0376 (7) | 0.0364 (7) | −0.0053 (6) | 0.0015 (6) | −0.0036 (5) |
N3 | 0.0516 (9) | 0.0518 (9) | 0.0469 (8) | −0.0093 (7) | −0.0069 (7) | −0.0050 (7) |
N4 | 0.0637 (11) | 0.0724 (12) | 0.0702 (12) | −0.0260 (10) | −0.0155 (9) | −0.0037 (9) |
N5 | 0.0521 (10) | 0.0899 (14) | 0.0863 (14) | −0.0200 (10) | −0.0137 (10) | −0.0073 (11) |
N6 | 0.0416 (7) | 0.0407 (7) | 0.0355 (7) | −0.0128 (6) | 0.0045 (6) | −0.0054 (5) |
N7 | 0.0473 (8) | 0.0405 (7) | 0.0373 (7) | −0.0087 (6) | −0.0008 (6) | −0.0064 (6) |
N8 | 0.0604 (9) | 0.0416 (8) | 0.0448 (8) | −0.0148 (7) | −0.0016 (7) | −0.0071 (6) |
N9 | 0.0698 (11) | 0.0609 (10) | 0.0560 (10) | −0.0271 (9) | −0.0017 (8) | 0.0030 (8) |
N10 | 0.0758 (12) | 0.0499 (10) | 0.0810 (13) | −0.0241 (9) | −0.0135 (10) | 0.0083 (9) |
C1 | 0.0545 (12) | 0.1051 (19) | 0.0653 (14) | −0.0181 (13) | 0.0020 (10) | −0.0203 (13) |
C2 | 0.0431 (10) | 0.0634 (12) | 0.0559 (11) | −0.0168 (9) | 0.0015 (8) | 0.0016 (9) |
C3 | 0.0472 (10) | 0.0429 (9) | 0.0567 (11) | −0.0171 (8) | −0.0030 (8) | 0.0018 (8) |
C4 | 0.0418 (8) | 0.0308 (7) | 0.0386 (8) | −0.0072 (6) | 0.0028 (7) | −0.0043 (6) |
C5 | 0.0425 (9) | 0.0396 (8) | 0.0460 (9) | −0.0136 (7) | 0.0073 (7) | −0.0022 (7) |
C6 | 0.0500 (10) | 0.0417 (9) | 0.0413 (9) | −0.0095 (7) | 0.0113 (7) | 0.0009 (7) |
C7 | 0.0603 (11) | 0.0495 (10) | 0.0418 (9) | −0.0025 (9) | −0.0060 (8) | −0.0097 (8) |
C8 | 0.0533 (10) | 0.0505 (10) | 0.0418 (9) | −0.0040 (8) | −0.0082 (8) | −0.0094 (8) |
C9 | 0.0643 (12) | 0.0578 (12) | 0.0552 (12) | −0.0103 (10) | 0.0005 (10) | −0.0045 (9) |
C10 | 0.0919 (18) | 0.0548 (12) | 0.0696 (15) | −0.0114 (12) | −0.0050 (13) | −0.0021 (11) |
C11 | 0.0889 (18) | 0.0569 (13) | 0.0788 (17) | 0.0043 (13) | −0.0147 (14) | −0.0070 (12) |
C12 | 0.0566 (13) | 0.0810 (17) | 0.0838 (17) | 0.0101 (12) | −0.0160 (12) | −0.0174 (14) |
C13 | 0.0504 (11) | 0.0677 (13) | 0.0602 (12) | −0.0071 (10) | −0.0115 (9) | −0.0116 (10) |
C14 | 0.0763 (15) | 0.0601 (13) | 0.0749 (15) | −0.0232 (11) | 0.0179 (12) | 0.0016 (11) |
C15 | 0.0576 (11) | 0.0547 (11) | 0.0579 (12) | −0.0180 (9) | 0.0107 (9) | −0.0043 (9) |
C16 | 0.0498 (10) | 0.0492 (10) | 0.0579 (11) | −0.0207 (8) | 0.0065 (8) | −0.0070 (8) |
C17 | 0.0412 (8) | 0.0387 (8) | 0.0399 (9) | −0.0104 (7) | 0.0005 (7) | −0.0033 (7) |
C18 | 0.0417 (8) | 0.0424 (8) | 0.0398 (8) | −0.0128 (7) | 0.0031 (7) | −0.0008 (7) |
C19 | 0.0453 (9) | 0.0474 (9) | 0.0357 (8) | −0.0081 (8) | 0.0054 (7) | 0.0001 (7) |
C20 | 0.0591 (11) | 0.0487 (10) | 0.0485 (10) | −0.0079 (9) | −0.0093 (8) | −0.0134 (8) |
C21 | 0.0556 (10) | 0.0435 (9) | 0.0462 (9) | −0.0171 (8) | −0.0044 (8) | −0.0127 (7) |
C22 | 0.0588 (11) | 0.0429 (10) | 0.0717 (13) | −0.0148 (9) | −0.0137 (10) | −0.0119 (9) |
C23 | 0.0652 (14) | 0.0539 (13) | 0.117 (2) | −0.0054 (11) | −0.0170 (15) | −0.0306 (14) |
C24 | 0.0666 (15) | 0.093 (2) | 0.108 (2) | −0.0155 (14) | 0.0076 (15) | −0.0582 (18) |
C25 | 0.0803 (16) | 0.111 (2) | 0.0647 (15) | −0.0379 (16) | 0.0163 (13) | −0.0341 (14) |
C26 | 0.0787 (15) | 0.0690 (13) | 0.0507 (11) | −0.0302 (12) | 0.0036 (10) | −0.0105 (10) |
C27 | 0.0441 (9) | 0.0410 (9) | 0.0393 (9) | −0.0093 (7) | −0.0013 (7) | −0.0004 (7) |
C28 | 0.0667 (13) | 0.0431 (10) | 0.0770 (14) | −0.0201 (9) | 0.0000 (11) | −0.0061 (9) |
C29 | 0.0490 (10) | 0.0528 (11) | 0.0603 (12) | −0.0189 (9) | 0.0091 (9) | 0.0016 (9) |
C30 | 0.0527 (13) | 0.0753 (16) | 0.112 (2) | −0.0080 (11) | 0.0152 (13) | 0.0079 (15) |
O1WA | 0.116 (4) | 0.165 (5) | 0.112 (4) | −0.056 (4) | −0.037 (3) | 0.035 (4) |
O1WB | 0.227 (10) | 0.203 (9) | 0.298 (12) | −0.147 (8) | 0.103 (8) | −0.106 (8) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.9603 (12) | C9—C10 | 1.375 (3) |
Zn1—O3 | 1.9617 (13) | C10—H10 | 0.9300 |
Zn1—N1 | 2.0460 (13) | C10—C11 | 1.382 (4) |
Zn1—N6 | 2.0234 (13) | C11—H11 | 0.9300 |
O1—C27 | 1.275 (2) | C11—C12 | 1.354 (4) |
O2—C27 | 1.221 (2) | C12—H12 | 0.9300 |
O3—C29 | 1.259 (2) | C12—C13 | 1.414 (3) |
O4—C29 | 1.210 (3) | C14—H14A | 0.9600 |
N1—C4 | 1.327 (2) | C14—H14B | 0.9600 |
N1—C5 | 1.386 (2) | C14—H14C | 0.9600 |
N2—C4 | 1.359 (2) | C14—C15 | 1.515 (3) |
N2—C6 | 1.385 (2) | C15—H15A | 0.9700 |
N2—C7 | 1.461 (2) | C15—H15B | 0.9700 |
N3—N4 | 1.360 (2) | C15—C16 | 1.536 (3) |
N3—C7 | 1.448 (2) | C16—H16A | 0.9700 |
N3—C8 | 1.369 (2) | C16—H16B | 0.9700 |
N4—N5 | 1.303 (3) | C16—C17 | 1.487 (2) |
N5—C13 | 1.375 (3) | C18—H18 | 0.9300 |
N6—C17 | 1.323 (2) | C18—C19 | 1.339 (2) |
N6—C18 | 1.381 (2) | C19—H19 | 0.9300 |
N7—C17 | 1.358 (2) | C20—H20A | 0.9700 |
N7—C19 | 1.377 (2) | C20—H20B | 0.9700 |
N7—C20 | 1.453 (2) | C21—C22 | 1.393 (3) |
N8—N9 | 1.360 (2) | C21—C26 | 1.391 (3) |
N8—C20 | 1.448 (2) | C22—C23 | 1.400 (3) |
N8—C21 | 1.358 (2) | C23—H23 | 0.9300 |
N9—N10 | 1.293 (3) | C23—C24 | 1.350 (4) |
N10—C22 | 1.365 (3) | C24—H24 | 0.9300 |
C1—H1A | 0.9600 | C24—C25 | 1.401 (4) |
C1—H1B | 0.9600 | C25—H25 | 0.9300 |
C1—H1C | 0.9600 | C25—C26 | 1.375 (3) |
C1—C2 | 1.495 (3) | C26—H26 | 0.9300 |
C2—H2A | 0.9700 | C27—C28 | 1.498 (3) |
C2—H2B | 0.9700 | C28—H28A | 0.9600 |
C2—C3 | 1.536 (3) | C28—H28B | 0.9600 |
C3—H3A | 0.9700 | C28—H28C | 0.9600 |
C3—H3B | 0.9700 | C29—C30 | 1.506 (3) |
C3—C4 | 1.481 (2) | C30—H30A | 0.9600 |
C5—H5 | 0.9300 | C30—H30B | 0.9600 |
C5—C6 | 1.342 (3) | C30—H30C | 0.9600 |
C6—H6 | 0.9300 | O1WA—H1WA | 0.8503 |
C7—H7A | 0.9700 | O1WA—H1WB | 0.8498 |
C7—H7B | 0.9700 | O1WB—O1WBi | 1.714 (17) |
C8—C9 | 1.388 (3) | O1WB—H1WC | 0.8502 |
C8—C13 | 1.388 (3) | O1WB—H1WD | 0.8497 |
C9—H9 | 0.9300 | | |
| | | |
O1—Zn1—O3 | 114.54 (6) | C13—C12—H12 | 121.3 |
O1—Zn1—N1 | 116.32 (6) | N5—C13—C8 | 109.01 (19) |
O1—Zn1—N6 | 98.55 (5) | N5—C13—C12 | 131.4 (2) |
O3—Zn1—N1 | 97.61 (6) | C8—C13—C12 | 119.6 (2) |
O3—Zn1—N6 | 116.53 (6) | H14A—C14—H14B | 109.5 |
N6—Zn1—N1 | 114.42 (5) | H14A—C14—H14C | 109.5 |
C27—O1—Zn1 | 115.14 (11) | H14B—C14—H14C | 109.5 |
C29—O3—Zn1 | 116.15 (12) | C15—C14—H14A | 109.5 |
C4—N1—Zn1 | 128.79 (11) | C15—C14—H14B | 109.5 |
C4—N1—C5 | 106.58 (13) | C15—C14—H14C | 109.5 |
C5—N1—Zn1 | 123.15 (11) | C14—C15—H15A | 109.3 |
C4—N2—C6 | 108.02 (14) | C14—C15—H15B | 109.3 |
C4—N2—C7 | 127.03 (16) | C14—C15—C16 | 111.55 (18) |
C6—N2—C7 | 124.43 (15) | H15A—C15—H15B | 108.0 |
N4—N3—C7 | 120.28 (17) | C16—C15—H15A | 109.3 |
N4—N3—C8 | 110.13 (16) | C16—C15—H15B | 109.3 |
C8—N3—C7 | 129.48 (18) | C15—C16—H16A | 109.1 |
N5—N4—N3 | 108.71 (18) | C15—C16—H16B | 109.1 |
N4—N5—C13 | 108.27 (19) | H16A—C16—H16B | 107.8 |
C17—N6—Zn1 | 128.88 (11) | C17—C16—C15 | 112.67 (16) |
C17—N6—C18 | 106.94 (14) | C17—C16—H16A | 109.1 |
C18—N6—Zn1 | 123.04 (11) | C17—C16—H16B | 109.1 |
C17—N7—C19 | 107.84 (14) | N6—C17—N7 | 109.36 (14) |
C17—N7—C20 | 127.45 (16) | N6—C17—C16 | 124.08 (15) |
C19—N7—C20 | 124.62 (15) | N7—C17—C16 | 126.52 (16) |
N9—N8—C20 | 119.81 (17) | N6—C18—H18 | 125.3 |
C21—N8—N9 | 109.92 (16) | C19—C18—N6 | 109.36 (15) |
C21—N8—C20 | 130.03 (16) | C19—C18—H18 | 125.3 |
N10—N9—N8 | 108.86 (17) | N7—C19—H19 | 126.8 |
N9—N10—C22 | 108.55 (17) | C18—C19—N7 | 106.49 (15) |
H1A—C1—H1B | 109.5 | C18—C19—H19 | 126.8 |
H1A—C1—H1C | 109.5 | N7—C20—H20A | 109.0 |
H1B—C1—H1C | 109.5 | N7—C20—H20B | 109.0 |
C2—C1—H1A | 109.5 | N8—C20—N7 | 112.73 (15) |
C2—C1—H1B | 109.5 | N8—C20—H20A | 109.0 |
C2—C1—H1C | 109.5 | N8—C20—H20B | 109.0 |
C1—C2—H2A | 108.9 | H20A—C20—H20B | 107.8 |
C1—C2—H2B | 108.9 | N8—C21—C22 | 103.92 (17) |
C1—C2—C3 | 113.31 (17) | N8—C21—C26 | 133.60 (19) |
H2A—C2—H2B | 107.7 | C26—C21—C22 | 122.5 (2) |
C3—C2—H2A | 108.9 | N10—C22—C21 | 108.75 (18) |
C3—C2—H2B | 108.9 | N10—C22—C23 | 130.9 (2) |
C2—C3—H3A | 108.9 | C21—C22—C23 | 120.4 (2) |
C2—C3—H3B | 108.9 | C22—C23—H23 | 121.2 |
H3A—C3—H3B | 107.7 | C24—C23—C22 | 117.6 (2) |
C4—C3—C2 | 113.28 (15) | C24—C23—H23 | 121.2 |
C4—C3—H3A | 108.9 | C23—C24—H24 | 119.3 |
C4—C3—H3B | 108.9 | C23—C24—C25 | 121.4 (2) |
N1—C4—N2 | 109.54 (14) | C25—C24—H24 | 119.3 |
N1—C4—C3 | 126.56 (15) | C24—C25—H25 | 118.6 |
N2—C4—C3 | 123.88 (16) | C26—C25—C24 | 122.8 (3) |
N1—C5—H5 | 125.1 | C26—C25—H25 | 118.6 |
C6—C5—N1 | 109.85 (15) | C21—C26—H26 | 122.3 |
C6—C5—H5 | 125.1 | C25—C26—C21 | 115.4 (2) |
N2—C6—H6 | 127.0 | C25—C26—H26 | 122.3 |
C5—C6—N2 | 106.01 (15) | O1—C27—C28 | 116.36 (16) |
C5—C6—H6 | 127.0 | O2—C27—O1 | 123.09 (17) |
N2—C7—H7A | 108.8 | O2—C27—C28 | 120.55 (18) |
N2—C7—H7B | 108.8 | C27—C28—H28A | 109.5 |
N3—C7—N2 | 113.63 (15) | C27—C28—H28B | 109.5 |
N3—C7—H7A | 108.8 | C27—C28—H28C | 109.5 |
N3—C7—H7B | 108.8 | H28A—C28—H28B | 109.5 |
H7A—C7—H7B | 107.7 | H28A—C28—H28C | 109.5 |
N3—C8—C9 | 133.38 (19) | H28B—C28—H28C | 109.5 |
N3—C8—C13 | 103.87 (19) | O3—C29—C30 | 117.3 (2) |
C13—C8—C9 | 122.74 (19) | O4—C29—O3 | 124.3 (2) |
C8—C9—H9 | 122.1 | O4—C29—C30 | 118.4 (2) |
C10—C9—C8 | 115.7 (2) | C29—C30—H30A | 109.5 |
C10—C9—H9 | 122.1 | C29—C30—H30B | 109.5 |
C9—C10—H10 | 118.7 | C29—C30—H30C | 109.5 |
C9—C10—C11 | 122.6 (3) | H30A—C30—H30B | 109.5 |
C11—C10—H10 | 118.7 | H30A—C30—H30C | 109.5 |
C10—C11—H11 | 119.1 | H30B—C30—H30C | 109.5 |
C12—C11—C10 | 121.9 (2) | H1WA—O1WA—H1WB | 109.5 |
C12—C11—H11 | 119.1 | O1WBi—O1WB—H1WC | 63.3 |
C11—C12—H12 | 121.3 | O1WBi—O1WB—H1WD | 51.8 |
C11—C12—C13 | 117.4 (2) | H1WC—O1WB—H1WD | 109.5 |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1WA—H1WA···O4ii | 0.85 | 2.00 | 2.802 (6) | 156 |
O1WB—H1WD···O1WAi | 0.85 | 2.27 | 2.774 (11) | 118 |
O1WB—H1WC···O4iii | 0.85 | 2.47 | 3.782 (11) | 130 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z; (iii) −x+2, −y, −z+1. |
Bis(azido-
κN1)bis[1-(1
H-benzotriazol-1-ylmethyl)-2-propyl-1
H-imidazole-
κN3]zinc(II) (2)
top
Crystal data top
[Zn(C13H15N5)2(N3)2] | Z = 2 |
Mr = 632.03 | F(000) = 656 |
Triclinic, P1 | Dx = 1.442 Mg m−3 |
a = 7.0870 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 13.7109 (7) Å | Cell parameters from 5404 reflections |
c = 15.2483 (8) Å | θ = 4.2–70.5° |
α = 84.360 (4)° | µ = 1.57 mm−1 |
β = 83.990 (4)° | T = 293 K |
γ = 82.531 (4)° | 0.16 × 0.14 × 0.07 mm |
V = 1455.62 (12) Å3 | |
Data collection top
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5469 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4707 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.018 |
Detector resolution: 15.9737 pixels mm-1 | θmax = 70.8°, θmin = 3.3° |
ω scans | h = −8→6 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −16→14 |
Tmin = 0.756, Tmax = 1.000 | l = −18→18 |
10761 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3428P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5469 reflections | Δρmax = 0.33 e Å−3 |
390 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | |
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 | 0.70419 (4) | 0.53789 (2) | 0.20223 (2) | 0.04551 (10) | |
N1 | 1.1637 (3) | 1.00454 (15) | 0.11518 (16) | 0.0651 (5) | |
N2 | 1.1872 (3) | 0.91273 (15) | 0.14636 (13) | 0.0578 (5) | |
N3 | 1.2613 (2) | 0.85709 (12) | 0.07890 (11) | 0.0453 (4) | |
N4 | 1.1438 (2) | 0.69873 (11) | 0.09370 (10) | 0.0407 (3) | |
N5 | 0.8941 (2) | 0.62122 (11) | 0.13413 (11) | 0.0433 (4) | |
N6 | 1.3659 (3) | 0.10093 (15) | 0.41227 (16) | 0.0688 (5) | |
N7 | 1.2803 (3) | 0.11395 (15) | 0.34044 (15) | 0.0649 (5) | |
N8 | 1.0882 (3) | 0.12699 (12) | 0.36241 (12) | 0.0529 (4) | |
N9 | 0.9502 (2) | 0.24770 (12) | 0.25558 (11) | 0.0457 (4) | |
N10 | 0.8578 (2) | 0.40489 (12) | 0.22523 (11) | 0.0430 (3) | |
N11 | 0.5142 (3) | 0.51494 (15) | 0.12130 (16) | 0.0669 (5) | |
N12 | 0.4989 (2) | 0.43475 (15) | 0.10514 (12) | 0.0526 (4) | |
N13 | 0.4763 (3) | 0.35666 (17) | 0.08858 (15) | 0.0691 (6) | |
N14 | 0.5834 (3) | 0.60288 (17) | 0.30590 (15) | 0.0722 (6) | |
N15 | 0.5493 (3) | 0.68601 (17) | 0.30555 (13) | 0.0584 (5) | |
N16 | 0.5106 (4) | 0.7709 (2) | 0.3086 (2) | 0.0967 (8) | |
C1 | 1.2235 (3) | 1.01033 (16) | 0.02659 (18) | 0.0566 (5) | |
C2 | 1.2330 (4) | 1.09229 (19) | −0.0373 (2) | 0.0761 (8) | |
H2 | 1.1910 | 1.1562 | −0.0226 | 0.091* | |
C3 | 1.3051 (4) | 1.0742 (2) | −0.1205 (2) | 0.0840 (9) | |
H3 | 1.3137 | 1.1270 | −0.1634 | 0.101* | |
C4 | 1.3670 (4) | 0.9790 (2) | −0.14407 (19) | 0.0753 (8) | |
H4 | 1.4153 | 0.9701 | −0.2022 | 0.090* | |
C5 | 1.3590 (3) | 0.89772 (19) | −0.08402 (16) | 0.0579 (5) | |
H5 | 1.3999 | 0.8341 | −0.1000 | 0.070* | |
C6 | 1.2863 (3) | 0.91582 (15) | 0.00186 (14) | 0.0457 (4) | |
C7 | 1.3088 (3) | 0.75198 (15) | 0.09614 (14) | 0.0459 (4) | |
H7A | 1.3569 | 0.7380 | 0.1539 | 0.055* | |
H7B | 1.4094 | 0.7287 | 0.0523 | 0.055* | |
C8 | 1.0838 (3) | 0.67134 (15) | 0.01798 (13) | 0.0479 (4) | |
H8 | 1.1388 | 0.6832 | −0.0396 | 0.057* | |
C9 | 0.9298 (3) | 0.62414 (15) | 0.04329 (13) | 0.0467 (4) | |
H9 | 0.8587 | 0.5977 | 0.0056 | 0.056* | |
C10 | 1.0262 (3) | 0.66784 (13) | 0.16360 (12) | 0.0407 (4) | |
C11 | 1.0386 (3) | 0.68435 (15) | 0.25759 (13) | 0.0490 (5) | |
H11A | 0.9166 | 0.7171 | 0.2809 | 0.059* | |
H11B | 1.1339 | 0.7286 | 0.2598 | 0.059* | |
C12 | 1.0890 (4) | 0.59146 (17) | 0.31714 (15) | 0.0575 (5) | |
H12A | 0.9946 | 0.5466 | 0.3154 | 0.069* | |
H12B | 1.2124 | 0.5589 | 0.2954 | 0.069* | |
C13 | 1.0959 (4) | 0.6144 (2) | 0.41158 (16) | 0.0714 (7) | |
H13A | 1.1925 | 0.6568 | 0.4138 | 0.107* | |
H13B | 1.1255 | 0.5541 | 0.4478 | 0.107* | |
H13C | 0.9740 | 0.6468 | 0.4332 | 0.107* | |
C14 | 1.2288 (3) | 0.10467 (15) | 0.48389 (17) | 0.0562 (5) | |
C15 | 1.2477 (4) | 0.09222 (17) | 0.57507 (18) | 0.0679 (7) | |
H15 | 1.3670 | 0.0813 | 0.5969 | 0.081* | |
C16 | 1.0838 (5) | 0.09684 (17) | 0.63000 (18) | 0.0701 (7) | |
H16 | 1.0915 | 0.0887 | 0.6908 | 0.084* | |
C17 | 0.9036 (4) | 0.11353 (16) | 0.59767 (17) | 0.0660 (7) | |
H17 | 0.7952 | 0.1161 | 0.6378 | 0.079* | |
C18 | 0.8816 (3) | 0.12623 (15) | 0.50887 (16) | 0.0565 (5) | |
H18 | 0.7615 | 0.1372 | 0.4878 | 0.068* | |
C19 | 1.0491 (3) | 0.12171 (13) | 0.45204 (15) | 0.0496 (5) | |
C20 | 0.9620 (4) | 0.14498 (15) | 0.29246 (15) | 0.0556 (5) | |
H20A | 0.8355 | 0.1296 | 0.3156 | 0.067* | |
H20B | 1.0089 | 0.1020 | 0.2460 | 0.067* | |
C21 | 1.1010 (3) | 0.28671 (16) | 0.20563 (14) | 0.0529 (5) | |
H21 | 1.2193 | 0.2530 | 0.1880 | 0.063* | |
C22 | 1.0427 (3) | 0.38280 (15) | 0.18773 (14) | 0.0484 (5) | |
H22 | 1.1155 | 0.4278 | 0.1550 | 0.058* | |
C23 | 0.8043 (3) | 0.32145 (14) | 0.26582 (13) | 0.0428 (4) | |
C24 | 0.6169 (3) | 0.31379 (17) | 0.31750 (15) | 0.0546 (5) | |
H24A | 0.5975 | 0.2448 | 0.3287 | 0.066* | |
H24B | 0.5161 | 0.3468 | 0.2830 | 0.066* | |
C25 | 0.6036 (4) | 0.3592 (2) | 0.40479 (17) | 0.0713 (7) | |
H25A | 0.6314 | 0.4270 | 0.3938 | 0.086* | |
H25B | 0.6991 | 0.3234 | 0.4409 | 0.086* | |
C26 | 0.4072 (6) | 0.3574 (3) | 0.4551 (2) | 0.1116 (13) | |
H26A | 0.3107 | 0.3818 | 0.4160 | 0.167* | |
H26B | 0.3961 | 0.3984 | 0.5034 | 0.167* | |
H26C | 0.3907 | 0.2909 | 0.4777 | 0.167* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.04149 (15) | 0.03957 (15) | 0.05500 (17) | −0.00964 (10) | 0.00147 (11) | −0.00185 (11) |
N1 | 0.0456 (10) | 0.0582 (12) | 0.0950 (16) | −0.0105 (9) | −0.0003 (10) | −0.0259 (11) |
N2 | 0.0458 (9) | 0.0670 (12) | 0.0638 (11) | −0.0167 (9) | 0.0074 (8) | −0.0220 (9) |
N3 | 0.0376 (8) | 0.0466 (9) | 0.0527 (9) | −0.0130 (7) | 0.0029 (7) | −0.0068 (7) |
N4 | 0.0381 (8) | 0.0402 (8) | 0.0439 (8) | −0.0094 (6) | −0.0004 (6) | −0.0012 (6) |
N5 | 0.0452 (8) | 0.0399 (8) | 0.0460 (9) | −0.0140 (7) | −0.0010 (7) | −0.0023 (7) |
N6 | 0.0573 (12) | 0.0595 (12) | 0.0855 (15) | −0.0012 (9) | −0.0056 (11) | 0.0048 (11) |
N7 | 0.0606 (12) | 0.0565 (11) | 0.0714 (13) | −0.0003 (9) | 0.0051 (10) | 0.0042 (10) |
N8 | 0.0563 (10) | 0.0415 (9) | 0.0576 (10) | −0.0011 (8) | −0.0028 (8) | 0.0026 (8) |
N9 | 0.0518 (9) | 0.0391 (8) | 0.0446 (9) | −0.0042 (7) | −0.0009 (7) | −0.0008 (7) |
N10 | 0.0396 (8) | 0.0420 (8) | 0.0463 (9) | −0.0065 (7) | −0.0004 (7) | 0.0000 (7) |
N11 | 0.0643 (12) | 0.0502 (11) | 0.0880 (15) | −0.0027 (9) | −0.0276 (11) | 0.0010 (10) |
N12 | 0.0351 (8) | 0.0681 (13) | 0.0536 (10) | −0.0076 (8) | −0.0005 (7) | −0.0016 (9) |
N13 | 0.0638 (12) | 0.0699 (13) | 0.0772 (14) | −0.0227 (10) | 0.0096 (11) | −0.0228 (11) |
N14 | 0.0778 (14) | 0.0676 (14) | 0.0677 (13) | −0.0166 (11) | 0.0245 (11) | −0.0111 (11) |
N15 | 0.0394 (9) | 0.0760 (15) | 0.0590 (11) | −0.0048 (9) | 0.0014 (8) | −0.0109 (10) |
N16 | 0.0883 (18) | 0.0708 (16) | 0.129 (2) | 0.0073 (14) | −0.0045 (17) | −0.0256 (16) |
C1 | 0.0354 (10) | 0.0493 (12) | 0.0877 (17) | −0.0095 (9) | −0.0123 (10) | −0.0061 (11) |
C2 | 0.0519 (13) | 0.0498 (13) | 0.130 (3) | −0.0126 (11) | −0.0324 (16) | 0.0093 (15) |
C3 | 0.0673 (17) | 0.083 (2) | 0.103 (2) | −0.0295 (15) | −0.0342 (17) | 0.0384 (18) |
C4 | 0.0595 (14) | 0.100 (2) | 0.0676 (16) | −0.0277 (15) | −0.0149 (12) | 0.0203 (15) |
C5 | 0.0465 (11) | 0.0703 (15) | 0.0576 (13) | −0.0146 (10) | −0.0053 (10) | 0.0020 (11) |
C6 | 0.0319 (9) | 0.0474 (11) | 0.0593 (12) | −0.0130 (8) | −0.0055 (8) | 0.0008 (9) |
C7 | 0.0346 (9) | 0.0507 (11) | 0.0526 (11) | −0.0116 (8) | −0.0010 (8) | −0.0006 (9) |
C8 | 0.0496 (11) | 0.0539 (11) | 0.0402 (10) | −0.0121 (9) | 0.0033 (8) | −0.0048 (8) |
C9 | 0.0498 (11) | 0.0467 (11) | 0.0458 (10) | −0.0126 (9) | −0.0026 (8) | −0.0072 (8) |
C10 | 0.0424 (10) | 0.0359 (9) | 0.0437 (10) | −0.0083 (7) | 0.0000 (8) | −0.0021 (7) |
C11 | 0.0527 (11) | 0.0486 (11) | 0.0476 (11) | −0.0168 (9) | 0.0012 (9) | −0.0064 (9) |
C12 | 0.0680 (14) | 0.0547 (12) | 0.0515 (12) | −0.0119 (11) | −0.0096 (10) | −0.0029 (10) |
C13 | 0.0936 (19) | 0.0752 (17) | 0.0465 (12) | −0.0199 (15) | −0.0033 (12) | −0.0007 (11) |
C14 | 0.0588 (13) | 0.0391 (10) | 0.0698 (14) | −0.0032 (9) | −0.0077 (11) | −0.0018 (9) |
C15 | 0.0837 (18) | 0.0469 (12) | 0.0769 (17) | −0.0056 (12) | −0.0274 (14) | −0.0059 (11) |
C16 | 0.106 (2) | 0.0439 (12) | 0.0609 (14) | −0.0028 (13) | −0.0126 (15) | −0.0104 (10) |
C17 | 0.0870 (18) | 0.0396 (11) | 0.0665 (15) | −0.0005 (11) | 0.0112 (13) | −0.0087 (10) |
C18 | 0.0611 (13) | 0.0360 (10) | 0.0693 (14) | −0.0003 (9) | 0.0000 (11) | −0.0031 (9) |
C19 | 0.0604 (12) | 0.0284 (9) | 0.0588 (12) | −0.0020 (8) | −0.0062 (10) | −0.0012 (8) |
C20 | 0.0686 (14) | 0.0378 (10) | 0.0604 (13) | −0.0057 (9) | −0.0093 (11) | −0.0016 (9) |
C21 | 0.0460 (11) | 0.0562 (12) | 0.0512 (12) | 0.0015 (9) | 0.0067 (9) | −0.0004 (9) |
C22 | 0.0428 (10) | 0.0496 (11) | 0.0502 (11) | −0.0082 (8) | 0.0041 (8) | 0.0028 (9) |
C23 | 0.0441 (10) | 0.0431 (10) | 0.0417 (10) | −0.0092 (8) | −0.0031 (8) | −0.0020 (8) |
C24 | 0.0497 (11) | 0.0552 (12) | 0.0570 (13) | −0.0118 (9) | 0.0038 (10) | 0.0021 (10) |
C25 | 0.0887 (19) | 0.0650 (15) | 0.0566 (14) | −0.0118 (13) | 0.0109 (13) | −0.0020 (11) |
C26 | 0.130 (3) | 0.091 (2) | 0.099 (2) | −0.011 (2) | 0.061 (2) | −0.0093 (19) |
Geometric parameters (Å, º) top
Zn1—N5 | 2.0171 (15) | C7—H7B | 0.9700 |
Zn1—N10 | 2.0177 (16) | C8—H8 | 0.9300 |
Zn1—N11 | 1.993 (2) | C8—C9 | 1.343 (3) |
Zn1—N14 | 1.955 (2) | C9—H9 | 0.9300 |
N1—N2 | 1.297 (3) | C10—C11 | 1.486 (3) |
N1—C1 | 1.371 (3) | C11—H11A | 0.9700 |
N2—N3 | 1.361 (2) | C11—H11B | 0.9700 |
N3—C6 | 1.367 (3) | C11—C12 | 1.515 (3) |
N3—C7 | 1.441 (3) | C12—H12A | 0.9700 |
N4—C7 | 1.462 (2) | C12—H12B | 0.9700 |
N4—C8 | 1.373 (3) | C12—C13 | 1.511 (3) |
N4—C10 | 1.352 (2) | C13—H13A | 0.9600 |
N5—C9 | 1.379 (3) | C13—H13B | 0.9600 |
N5—C10 | 1.337 (2) | C13—H13C | 0.9600 |
N6—N7 | 1.293 (3) | C14—C15 | 1.402 (4) |
N6—C14 | 1.384 (3) | C14—C19 | 1.393 (3) |
N7—N8 | 1.361 (3) | C15—H15 | 0.9300 |
N8—C19 | 1.362 (3) | C15—C16 | 1.357 (4) |
N8—C20 | 1.445 (3) | C16—H16 | 0.9300 |
N9—C20 | 1.459 (3) | C16—C17 | 1.400 (4) |
N9—C21 | 1.381 (3) | C17—H17 | 0.9300 |
N9—C23 | 1.357 (3) | C17—C18 | 1.371 (4) |
N10—C22 | 1.382 (2) | C18—H18 | 0.9300 |
N10—C23 | 1.327 (2) | C18—C19 | 1.393 (3) |
N11—N12 | 1.171 (3) | C20—H20A | 0.9700 |
N12—N13 | 1.158 (3) | C20—H20B | 0.9700 |
N14—N15 | 1.134 (3) | C21—H21 | 0.9300 |
N15—N16 | 1.165 (3) | C21—C22 | 1.339 (3) |
C1—C2 | 1.417 (4) | C22—H22 | 0.9300 |
C1—C6 | 1.389 (3) | C23—C24 | 1.482 (3) |
C2—H2 | 0.9300 | C24—H24A | 0.9700 |
C2—C3 | 1.351 (5) | C24—H24B | 0.9700 |
C3—H3 | 0.9300 | C24—C25 | 1.513 (3) |
C3—C4 | 1.391 (5) | C25—H25A | 0.9700 |
C4—H4 | 0.9300 | C25—H25B | 0.9700 |
C4—C5 | 1.374 (3) | C25—C26 | 1.519 (4) |
C5—H5 | 0.9300 | C26—H26A | 0.9600 |
C5—C6 | 1.390 (3) | C26—H26B | 0.9600 |
C7—H7A | 0.9700 | C26—H26C | 0.9600 |
| | | |
N5—Zn1—N10 | 103.99 (6) | C10—C11—C12 | 114.76 (17) |
N11—Zn1—N5 | 108.56 (8) | H11A—C11—H11B | 107.6 |
N11—Zn1—N10 | 104.84 (7) | C12—C11—H11A | 108.6 |
N14—Zn1—N5 | 109.95 (8) | C12—C11—H11B | 108.6 |
N14—Zn1—N10 | 116.78 (9) | C11—C12—H12A | 109.3 |
N14—Zn1—N11 | 112.14 (10) | C11—C12—H12B | 109.3 |
N2—N1—C1 | 108.72 (19) | H12A—C12—H12B | 108.0 |
N1—N2—N3 | 108.36 (19) | C13—C12—C11 | 111.5 (2) |
N2—N3—C6 | 110.37 (17) | C13—C12—H12A | 109.3 |
N2—N3—C7 | 119.91 (17) | C13—C12—H12B | 109.3 |
C6—N3—C7 | 129.65 (17) | C12—C13—H13A | 109.5 |
C8—N4—C7 | 124.59 (16) | C12—C13—H13B | 109.5 |
C10—N4—C7 | 126.86 (16) | C12—C13—H13C | 109.5 |
C10—N4—C8 | 108.56 (15) | H13A—C13—H13B | 109.5 |
C9—N5—Zn1 | 122.32 (13) | H13A—C13—H13C | 109.5 |
C10—N5—Zn1 | 129.66 (13) | H13B—C13—H13C | 109.5 |
C10—N5—C9 | 107.12 (16) | N6—C14—C15 | 130.7 (2) |
N7—N6—C14 | 108.5 (2) | N6—C14—C19 | 108.4 (2) |
N6—N7—N8 | 108.8 (2) | C19—C14—C15 | 121.0 (2) |
N7—N8—C19 | 110.36 (19) | C14—C15—H15 | 121.5 |
N7—N8—C20 | 118.88 (19) | C16—C15—C14 | 117.0 (3) |
C19—N8—C20 | 130.76 (19) | C16—C15—H15 | 121.5 |
C21—N9—C20 | 122.76 (18) | C15—C16—H16 | 119.1 |
C23—N9—C20 | 129.07 (18) | C15—C16—C17 | 121.9 (3) |
C23—N9—C21 | 108.09 (16) | C17—C16—H16 | 119.1 |
C22—N10—Zn1 | 122.53 (13) | C16—C17—H17 | 118.9 |
C23—N10—Zn1 | 130.13 (13) | C18—C17—C16 | 122.2 (3) |
C23—N10—C22 | 106.81 (16) | C18—C17—H17 | 118.9 |
N12—N11—Zn1 | 120.43 (16) | C17—C18—H18 | 121.9 |
N13—N12—N11 | 177.3 (2) | C17—C18—C19 | 116.2 (2) |
N15—N14—Zn1 | 122.67 (18) | C19—C18—H18 | 121.9 |
N14—N15—N16 | 177.3 (3) | N8—C19—C14 | 104.0 (2) |
N1—C1—C2 | 131.5 (2) | N8—C19—C18 | 134.2 (2) |
N1—C1—C6 | 108.9 (2) | C18—C19—C14 | 121.7 (2) |
C6—C1—C2 | 119.5 (3) | N8—C20—N9 | 111.03 (17) |
C1—C2—H2 | 121.2 | N8—C20—H20A | 109.4 |
C3—C2—C1 | 117.6 (3) | N8—C20—H20B | 109.4 |
C3—C2—H2 | 121.2 | N9—C20—H20A | 109.4 |
C2—C3—H3 | 119.0 | N9—C20—H20B | 109.4 |
C2—C3—C4 | 122.0 (3) | H20A—C20—H20B | 108.0 |
C4—C3—H3 | 119.0 | N9—C21—H21 | 126.9 |
C3—C4—H4 | 119.0 | C22—C21—N9 | 106.17 (18) |
C5—C4—C3 | 122.0 (3) | C22—C21—H21 | 126.9 |
C5—C4—H4 | 119.0 | N10—C22—H22 | 125.2 |
C4—C5—H5 | 121.8 | C21—C22—N10 | 109.65 (18) |
C4—C5—C6 | 116.3 (3) | C21—C22—H22 | 125.2 |
C6—C5—H5 | 121.8 | N9—C23—C24 | 126.60 (18) |
N3—C6—C1 | 103.61 (19) | N10—C23—N9 | 109.27 (17) |
N3—C6—C5 | 133.8 (2) | N10—C23—C24 | 124.07 (18) |
C1—C6—C5 | 122.5 (2) | C23—C24—H24A | 109.2 |
N3—C7—N4 | 111.99 (15) | C23—C24—H24B | 109.2 |
N3—C7—H7A | 109.2 | C23—C24—C25 | 112.1 (2) |
N3—C7—H7B | 109.2 | H24A—C24—H24B | 107.9 |
N4—C7—H7A | 109.2 | C25—C24—H24A | 109.2 |
N4—C7—H7B | 109.2 | C25—C24—H24B | 109.2 |
H7A—C7—H7B | 107.9 | C24—C25—H25A | 109.2 |
N4—C8—H8 | 126.7 | C24—C25—H25B | 109.2 |
C9—C8—N4 | 106.53 (17) | C24—C25—C26 | 112.1 (3) |
C9—C8—H8 | 126.7 | H25A—C25—H25B | 107.9 |
N5—C9—H9 | 125.5 | C26—C25—H25A | 109.2 |
C8—C9—N5 | 109.09 (18) | C26—C25—H25B | 109.2 |
C8—C9—H9 | 125.5 | C25—C26—H26A | 109.5 |
N4—C10—C11 | 125.92 (17) | C25—C26—H26B | 109.5 |
N5—C10—N4 | 108.70 (16) | C25—C26—H26C | 109.5 |
N5—C10—C11 | 125.37 (17) | H26A—C26—H26B | 109.5 |
C10—C11—H11A | 108.6 | H26A—C26—H26C | 109.5 |
C10—C11—H11B | 108.6 | H26B—C26—H26C | 109.5 |
| | | |
Zn1—N5—C9—C8 | −169.50 (14) | C6—N3—C7—N4 | −97.6 (2) |
Zn1—N5—C10—N4 | 168.56 (13) | C6—C1—C2—C3 | −0.5 (3) |
Zn1—N5—C10—C11 | −12.5 (3) | C7—N3—C6—C1 | −176.91 (18) |
Zn1—N10—C22—C21 | −172.60 (15) | C7—N3—C6—C5 | 1.4 (3) |
Zn1—N10—C23—N9 | 172.12 (13) | C7—N4—C8—C9 | 179.78 (18) |
Zn1—N10—C23—C24 | −10.7 (3) | C7—N4—C10—N5 | −179.39 (17) |
N1—N2—N3—C6 | 0.2 (2) | C7—N4—C10—C11 | 1.7 (3) |
N1—N2—N3—C7 | 177.55 (16) | C8—N4—C7—N3 | 83.9 (2) |
N1—C1—C2—C3 | 178.1 (2) | C8—N4—C10—N5 | 0.3 (2) |
N1—C1—C6—N3 | −0.4 (2) | C8—N4—C10—C11 | −178.60 (19) |
N1—C1—C6—C5 | −178.90 (18) | C9—N5—C10—N4 | −0.6 (2) |
N2—N1—C1—C2 | −178.2 (2) | C9—N5—C10—C11 | 178.36 (19) |
N2—N1—C1—C6 | 0.5 (2) | C10—N4—C7—N3 | −96.5 (2) |
N2—N3—C6—C1 | 0.1 (2) | C10—N4—C8—C9 | 0.1 (2) |
N2—N3—C6—C5 | 178.4 (2) | C10—N5—C9—C8 | 0.6 (2) |
N2—N3—C7—N4 | 85.6 (2) | C10—C11—C12—C13 | −179.2 (2) |
N4—C8—C9—N5 | −0.4 (2) | C14—N6—N7—N8 | 0.4 (3) |
N4—C10—C11—C12 | −114.0 (2) | C14—C15—C16—C17 | −0.2 (4) |
N5—C10—C11—C12 | 67.2 (3) | C15—C14—C19—N8 | −178.4 (2) |
N6—N7—N8—C19 | −0.3 (2) | C15—C14—C19—C18 | −0.6 (3) |
N6—N7—N8—C20 | 178.77 (18) | C15—C16—C17—C18 | 0.0 (4) |
N6—C14—C15—C16 | −177.8 (2) | C16—C17—C18—C19 | 0.0 (3) |
N6—C14—C19—N8 | 0.2 (2) | C17—C18—C19—N8 | 177.4 (2) |
N6—C14—C19—C18 | 178.00 (19) | C17—C18—C19—C14 | 0.3 (3) |
N7—N6—C14—C15 | 178.0 (2) | C19—N8—C20—N9 | 99.6 (2) |
N7—N6—C14—C19 | −0.4 (3) | C19—C14—C15—C16 | 0.5 (3) |
N7—N8—C19—C14 | 0.0 (2) | C20—N8—C19—C14 | −178.8 (2) |
N7—N8—C19—C18 | −177.4 (2) | C20—N8—C19—C18 | 3.8 (4) |
N7—N8—C20—N9 | −79.2 (2) | C20—N9—C21—C22 | −176.54 (19) |
N9—C21—C22—N10 | −0.2 (2) | C20—N9—C23—N10 | 176.19 (19) |
N9—C23—C24—C25 | 104.2 (2) | C20—N9—C23—C24 | −0.9 (3) |
N10—C23—C24—C25 | −72.5 (3) | C21—N9—C20—N8 | 69.5 (3) |
C1—N1—N2—N3 | −0.4 (2) | C21—N9—C23—N10 | −0.6 (2) |
C1—C2—C3—C4 | 0.6 (4) | C21—N9—C23—C24 | −177.7 (2) |
C2—C1—C6—N3 | 178.50 (18) | C22—N10—C23—N9 | 0.4 (2) |
C2—C1—C6—C5 | 0.0 (3) | C22—N10—C23—C24 | 177.60 (19) |
C2—C3—C4—C5 | −0.2 (4) | C23—N9—C20—N8 | −106.8 (2) |
C3—C4—C5—C6 | −0.3 (3) | C23—N9—C21—C22 | 0.5 (2) |
C4—C5—C6—N3 | −177.6 (2) | C23—N10—C22—C21 | −0.1 (2) |
C4—C5—C6—C1 | 0.4 (3) | C23—C24—C25—C26 | 176.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···N13i | 0.97 | 2.55 | 3.436 (3) | 151 |
C17—H17···N16ii | 0.93 | 2.60 | 3.395 (4) | 144 |
C20—H20B···N1iii | 0.97 | 2.58 | 3.544 (3) | 173 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z. |
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