metal-organic compounds
The Zn atom in each of the two symmetry-independent complex molecules of the title compound, [ZnCl2(C21H15N3)]·H2O, shows trigonal-bipyramidal coordination as the N-heterocycle is able to span the two axial sites of the coordination polyhedron. One of the molecules occupies a position in the crystal structure such that it does not interact with any water molecule; the other interacts with two water molecules to give rise to a hydrogen-bonded chain that runs along the a axis of the triclinic unit cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021853/ci6424sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021853/ci6424Isup2.hkl |
CCDC reference: 252761
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.
Crystal data top
[Zn(C21H15N3)Cl2]·H2O | Z = 4 |
Mr = 463.65 | F(000) = 944 |
Triclinic, P1 | Dx = 1.574 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8813 (6) Å | Cell parameters from 2259 reflections |
b = 16.355 (1) Å | θ = 2.4–19.4° |
c = 17.228 (1) Å | µ = 1.55 mm−1 |
α = 117.131 (1)° | T = 298 K |
β = 95.273 (1)° | Prism, orange |
γ = 93.091 (1)° | 0.41 × 0.34 × 0.21 mm |
V = 1956.4 (2) Å3 |
Data collection top
Bruker APEX area-detector diffractometer | 8709 independent reflections |
Radiation source: fine-focus sealed tube | 5414 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scan | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.580, Tmax = 0.722 | k = −20→21 |
16985 measured reflections | l = −22→22 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3 |
8709 reflections | (Δ/σ)max = 0.001 |
505 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.33831 (7) | 0.35239 (4) | 0.03168 (4) | 0.0421 (2) | |
Zn2 | 0.58293 (9) | 0.78552 (4) | 0.58255 (4) | 0.0505 (2) | |
Cl1 | 0.0808 (2) | 0.28211 (9) | 0.03034 (9) | 0.0534 (3) | |
Cl2 | 0.5263 (2) | 0.25229 (9) | −0.03688 (9) | 0.0563 (4) | |
Cl3 | 0.3358 (2) | 0.6888 (1) | 0.5376 (1) | 0.0899 (6) | |
Cl4 | 0.7071 (3) | 0.7733 (1) | 0.4643 (1) | 0.0908 (6) | |
O1w | −0.0073 (8) | 0.6236 (4) | 0.3992 (4) | 0.120 (2) | |
O2w | 0.062 (2) | 0.843 (1) | 0.596 (1) | 0.355 (8) | |
N1 | 0.2763 (5) | 0.3992 (3) | −0.0665 (3) | 0.044 (1) | |
N2 | 0.3217 (5) | 0.4952 (3) | 0.1032 (3) | 0.043 (1) | |
N3 | 0.4541 (5) | 0.3941 (3) | 0.1665 (3) | 0.045 (1) | |
N4 | 0.7463 (6) | 0.7024 (3) | 0.6211 (3) | 0.052 (1) | |
N5 | 0.6473 (5) | 0.8614 (3) | 0.7193 (3) | 0.040 (1) | |
N6 | 0.4846 (5) | 0.9169 (3) | 0.6179 (3) | 0.047 (1) | |
C1 | 0.2704 (7) | 0.3460 (4) | −0.1539 (3) | 0.054 (1) | |
C2 | 0.2233 (7) | 0.3769 (4) | −0.2134 (3) | 0.055 (1) | |
C3 | 0.1784 (7) | 0.4643 (4) | −0.1833 (3) | 0.053 (1) | |
C4 | 0.1857 (7) | 0.5210 (3) | −0.0939 (3) | 0.048 (1) | |
C5 | 0.2352 (6) | 0.4856 (3) | −0.0369 (3) | 0.040 (1) | |
C6 | 0.2511 (6) | 0.5389 (3) | 0.0606 (3) | 0.040 (1) | |
C7 | 0.1992 (6) | 0.6257 (3) | 0.1066 (3) | 0.045 (1) | |
C8 | 0.2245 (6) | 0.6709 (3) | 0.1981 (3) | 0.045 (1) | |
C9 | 0.3034 (7) | 0.6248 (3) | 0.2404 (3) | 0.047 (1) | |
C10 | 0.3485 (6) | 0.5367 (3) | 0.1905 (3) | 0.042 (1) | |
C11 | 0.4333 (7) | 0.4798 (3) | 0.2278 (3) | 0.047 (1) | |
C12 | 0.4852 (8) | 0.5097 (4) | 0.3154 (3) | 0.059 (2) | |
C13 | 0.5634 (9) | 0.4508 (5) | 0.3416 (4) | 0.072 (2) | |
C14 | 0.5885 (8) | 0.3644 (4) | 0.2792 (4) | 0.061 (2) | |
C15 | 0.5310 (7) | 0.3385 (4) | 0.1924 (4) | 0.054 (1) | |
C16 | 0.1690 (6) | 0.7640 (3) | 0.2494 (4) | 0.050 (1) | |
C17 | 0.1457 (7) | 0.8221 (4) | 0.2103 (4) | 0.059 (2) | |
C18 | 0.0926 (8) | 0.9087 (4) | 0.2579 (5) | 0.073 (2) | |
C19 | 0.0605 (8) | 0.9385 (5) | 0.3429 (5) | 0.078 (2) | |
C20 | 0.0786 (8) | 0.8804 (5) | 0.3807 (5) | 0.079 (2) | |
C21 | 0.1337 (8) | 0.7943 (4) | 0.3353 (4) | 0.065 (2) | |
C22 | 0.7909 (9) | 0.6200 (4) | 0.5652 (4) | 0.066 (2) | |
C23 | 0.8710 (9) | 0.5636 (4) | 0.5921 (4) | 0.069 (2) | |
C24 | 0.9070 (8) | 0.5934 (4) | 0.6812 (4) | 0.062 (2) | |
C25 | 0.8641 (7) | 0.6773 (3) | 0.7393 (4) | 0.050 (1) | |
C26 | 0.7827 (6) | 0.7313 (3) | 0.7067 (3) | 0.041 (1) | |
C27 | 0.7299 (6) | 0.8235 (3) | 0.7640 (3) | 0.039 (1) | |
C28 | 0.7634 (6) | 0.8684 (3) | 0.8540 (3) | 0.043 (1) | |
C29 | 0.7122 (6) | 0.9567 (3) | 0.9016 (3) | 0.039 (1) | |
C30 | 0.6271 (6) | 0.9953 (3) | 0.8531 (3) | 0.041 (1) | |
C31 | 0.5981 (6) | 0.9454 (3) | 0.7626 (3) | 0.041 (1) | |
C32 | 0.5089 (6) | 0.9785 (3) | 0.7037 (3) | 0.041 (1) | |
C33 | 0.4574 (7) | 1.0657 (3) | 0.7325 (4) | 0.050 (1) | |
C34 | 0.3820 (7) | 1.0903 (4) | 0.6722 (4) | 0.058 (2) | |
C35 | 0.3573 (8) | 1.0276 (4) | 0.5849 (4) | 0.059 (2) | |
C36 | 0.4095 (7) | 0.9427 (4) | 0.5608 (4) | 0.056 (1) | |
C37 | 0.7468 (6) | 1.0071 (3) | 0.9991 (3) | 0.042 (1) | |
C38 | 0.7632 (7) | 0.9597 (4) | 1.0482 (3) | 0.053 (1) | |
C39 | 0.7965 (8) | 1.0061 (5) | 1.1381 (4) | 0.069 (2) | |
C40 | 0.8126 (7) | 1.1002 (5) | 1.1820 (4) | 0.067 (2) | |
C41 | 0.7964 (8) | 1.1482 (4) | 1.1340 (4) | 0.071 (2) | |
C42 | 0.7632 (7) | 1.1016 (4) | 1.0433 (4) | 0.054 (1) | |
H1w1 | 0.0789 | 0.6511 | 0.3881 | 0.144* | |
H1w2 | −0.0920 | 0.6547 | 0.3977 | 0.144* | |
H2w1 | 0.1220 | 0.7979 | 0.5832 | 0.425* | |
H2w2 | −0.0398 | 0.8178 | 0.5658 | 0.425* | |
H1 | 0.2996 | 0.2859 | −0.1746 | 0.064* | |
H2 | 0.2220 | 0.3389 | −0.2734 | 0.066* | |
H3 | 0.1427 | 0.4859 | −0.2229 | 0.063* | |
H4 | 0.1582 | 0.5814 | −0.0725 | 0.057* | |
H7 | 0.1470 | 0.6542 | 0.0762 | 0.054* | |
H9 | 0.3254 | 0.6530 | 0.3015 | 0.057* | |
H12 | 0.4682 | 0.5688 | 0.3569 | 0.071* | |
H13 | 0.5985 | 0.4697 | 0.4008 | 0.086* | |
H14 | 0.6429 | 0.3241 | 0.2951 | 0.073* | |
H15 | 0.5466 | 0.2796 | 0.1499 | 0.065* | |
H17 | 0.1659 | 0.8025 | 0.1524 | 0.071* | |
H18 | 0.0785 | 0.9471 | 0.2318 | 0.088* | |
H19 | 0.0270 | 0.9971 | 0.3748 | 0.093* | |
H20 | 0.0532 | 0.8996 | 0.4377 | 0.095* | |
H21 | 0.1473 | 0.7566 | 0.3622 | 0.078* | |
H22 | 0.7659 | 0.6002 | 0.5051 | 0.079* | |
H23 | 0.9004 | 0.5069 | 0.5516 | 0.082* | |
H24 | 0.9606 | 0.5564 | 0.7017 | 0.074* | |
H25 | 0.8885 | 0.6982 | 0.7996 | 0.060* | |
H28 | 0.8202 | 0.8403 | 0.8835 | 0.052* | |
H30 | 0.5907 | 1.0537 | 0.8816 | 0.049* | |
H33 | 0.4735 | 1.1075 | 0.7921 | 0.060* | |
H34 | 0.3480 | 1.1492 | 0.6906 | 0.070* | |
H35 | 0.3060 | 1.0428 | 0.5430 | 0.071* | |
H36 | 0.3921 | 0.9000 | 0.5015 | 0.067* | |
H38 | 0.7515 | 0.8955 | 1.0196 | 0.063* | |
H39 | 0.8082 | 0.9729 | 1.1697 | 0.083* | |
H40 | 0.8341 | 1.1314 | 1.2431 | 0.080* | |
H41 | 0.8079 | 1.2125 | 1.1629 | 0.085* | |
H42 | 0.7518 | 1.1349 | 1.0118 | 0.064* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0519 (4) | 0.0350 (3) | 0.0402 (3) | 0.0087 (3) | 0.0098 (3) | 0.0170 (3) |
Zn2 | 0.0700 (5) | 0.0406 (3) | 0.0394 (3) | 0.0146 (3) | 0.0053 (3) | 0.0168 (3) |
Cl1 | 0.0509 (8) | 0.0531 (8) | 0.0634 (9) | 0.0038 (6) | 0.0063 (6) | 0.0336 (7) |
Cl2 | 0.0649 (9) | 0.0485 (8) | 0.0566 (8) | 0.0207 (7) | 0.0199 (7) | 0.0217 (7) |
Cl3 | 0.088 (1) | 0.066 (1) | 0.102 (1) | −0.011 (1) | −0.027 (1) | 0.037 (1) |
Cl4 | 0.142 (2) | 0.093 (1) | 0.073 (1) | 0.068 (1) | 0.054 (1) | 0.057 (1) |
O1w | 0.154 (6) | 0.112 (4) | 0.104 (4) | 0.048 (4) | 0.019 (4) | 0.055 (4) |
O2w | 0.27 (2) | 0.35 (2) | 0.36 (2) | −0.03 (1) | 0.03 (1) | 0.10 (1) |
N1 | 0.059 (3) | 0.036 (2) | 0.040 (2) | 0.010 (2) | 0.013 (2) | 0.018 (2) |
N2 | 0.048 (2) | 0.037 (2) | 0.042 (2) | 0.004 (2) | 0.007 (2) | 0.018 (2) |
N3 | 0.051 (3) | 0.044 (2) | 0.042 (2) | 0.006 (2) | 0.006 (2) | 0.023 (2) |
N4 | 0.077 (3) | 0.038 (2) | 0.042 (3) | 0.020 (2) | 0.012 (2) | 0.016 (2) |
N5 | 0.047 (2) | 0.033 (2) | 0.040 (2) | 0.009 (2) | 0.005 (2) | 0.016 (2) |
N6 | 0.054 (3) | 0.046 (2) | 0.044 (2) | 0.015 (2) | 0.008 (2) | 0.023 (2) |
C1 | 0.073 (4) | 0.046 (3) | 0.041 (3) | 0.016 (3) | 0.013 (3) | 0.018 (3) |
C2 | 0.071 (4) | 0.054 (3) | 0.037 (3) | 0.002 (3) | 0.006 (3) | 0.020 (3) |
C3 | 0.060 (4) | 0.061 (4) | 0.044 (3) | 0.006 (3) | 0.002 (3) | 0.031 (3) |
C4 | 0.055 (3) | 0.041 (3) | 0.048 (3) | 0.010 (2) | 0.010 (2) | 0.021 (2) |
C5 | 0.042 (3) | 0.037 (3) | 0.042 (3) | 0.004 (2) | 0.010 (2) | 0.018 (2) |
C6 | 0.043 (3) | 0.038 (3) | 0.042 (3) | 0.002 (2) | 0.009 (2) | 0.020 (2) |
C7 | 0.043 (3) | 0.041 (3) | 0.056 (3) | 0.003 (2) | 0.009 (2) | 0.026 (3) |
C8 | 0.045 (3) | 0.034 (3) | 0.046 (3) | 0.000 (2) | 0.011 (2) | 0.010 (2) |
C9 | 0.059 (3) | 0.040 (3) | 0.037 (3) | 0.004 (2) | 0.006 (2) | 0.014 (2) |
C10 | 0.047 (3) | 0.035 (3) | 0.039 (3) | 0.003 (2) | 0.006 (2) | 0.013 (2) |
C11 | 0.051 (3) | 0.043 (3) | 0.047 (3) | 0.001 (2) | 0.007 (2) | 0.021 (2) |
C12 | 0.079 (4) | 0.047 (3) | 0.037 (3) | −0.001 (3) | −0.004 (3) | 0.011 (3) |
C13 | 0.090 (5) | 0.071 (4) | 0.055 (4) | −0.005 (4) | −0.009 (3) | 0.034 (3) |
C14 | 0.067 (4) | 0.058 (4) | 0.059 (4) | 0.008 (3) | −0.002 (3) | 0.030 (3) |
C15 | 0.063 (4) | 0.048 (3) | 0.053 (3) | 0.015 (3) | 0.007 (3) | 0.025 (3) |
C16 | 0.042 (3) | 0.035 (3) | 0.055 (3) | 0.004 (2) | 0.007 (2) | 0.007 (2) |
C17 | 0.054 (3) | 0.046 (3) | 0.072 (4) | 0.009 (3) | 0.017 (3) | 0.020 (3) |
C18 | 0.060 (4) | 0.048 (4) | 0.108 (6) | 0.011 (3) | 0.019 (4) | 0.032 (4) |
C19 | 0.063 (4) | 0.053 (4) | 0.094 (6) | 0.020 (3) | 0.021 (4) | 0.011 (4) |
C20 | 0.070 (4) | 0.071 (4) | 0.065 (4) | 0.024 (4) | 0.017 (3) | 0.001 (4) |
C21 | 0.073 (4) | 0.055 (4) | 0.053 (4) | 0.020 (3) | 0.016 (3) | 0.011 (3) |
C22 | 0.101 (5) | 0.045 (3) | 0.048 (3) | 0.020 (3) | 0.017 (3) | 0.016 (3) |
C23 | 0.095 (5) | 0.046 (3) | 0.067 (4) | 0.030 (3) | 0.028 (4) | 0.023 (3) |
C24 | 0.066 (4) | 0.054 (3) | 0.076 (4) | 0.026 (3) | 0.015 (3) | 0.038 (3) |
C25 | 0.055 (3) | 0.049 (3) | 0.048 (3) | 0.018 (3) | 0.012 (3) | 0.023 (3) |
C26 | 0.045 (3) | 0.037 (3) | 0.045 (3) | 0.010 (2) | 0.009 (2) | 0.019 (2) |
C27 | 0.045 (3) | 0.033 (2) | 0.041 (3) | 0.008 (2) | 0.007 (2) | 0.018 (2) |
C28 | 0.043 (3) | 0.043 (3) | 0.050 (3) | 0.013 (2) | 0.009 (2) | 0.026 (2) |
C29 | 0.038 (3) | 0.041 (3) | 0.038 (3) | 0.004 (2) | 0.003 (2) | 0.018 (2) |
C30 | 0.044 (3) | 0.034 (2) | 0.043 (3) | 0.011 (2) | 0.010 (2) | 0.015 (2) |
C31 | 0.040 (3) | 0.037 (3) | 0.050 (3) | 0.010 (2) | 0.007 (2) | 0.023 (2) |
C32 | 0.046 (3) | 0.039 (3) | 0.039 (3) | 0.007 (2) | 0.002 (2) | 0.020 (2) |
C33 | 0.057 (3) | 0.039 (3) | 0.049 (3) | 0.009 (2) | 0.002 (3) | 0.016 (2) |
C34 | 0.062 (4) | 0.050 (3) | 0.069 (4) | 0.022 (3) | 0.010 (3) | 0.031 (3) |
C35 | 0.073 (4) | 0.060 (4) | 0.052 (3) | 0.024 (3) | 0.005 (3) | 0.032 (3) |
C36 | 0.073 (4) | 0.051 (3) | 0.043 (3) | 0.018 (3) | 0.003 (3) | 0.021 (3) |
C37 | 0.035 (3) | 0.047 (3) | 0.043 (3) | 0.009 (2) | 0.003 (2) | 0.019 (2) |
C38 | 0.060 (4) | 0.053 (3) | 0.045 (3) | 0.011 (3) | 0.011 (3) | 0.021 (3) |
C39 | 0.071 (4) | 0.094 (5) | 0.057 (4) | 0.018 (4) | 0.017 (3) | 0.044 (4) |
C40 | 0.052 (4) | 0.094 (5) | 0.042 (3) | 0.014 (3) | 0.001 (3) | 0.021 (3) |
C41 | 0.059 (4) | 0.062 (4) | 0.065 (4) | 0.011 (3) | −0.005 (3) | 0.009 (3) |
C42 | 0.052 (3) | 0.048 (3) | 0.055 (3) | 0.006 (3) | −0.005 (3) | 0.022 (3) |
Geometric parameters (Å, º) top
Zn1—N1 | 2.180 (4) | C14—H14 | 0.93 |
Zn1—N2 | 2.104 (4) | C15—H15 | 0.93 |
Zn1—N3 | 2.189 (4) | C16—C21 | 1.392 (7) |
Zn1—Cl1 | 2.271 (1) | C16—C17 | 1.403 (8) |
Zn1—Cl2 | 2.256 (1) | C17—C18 | 1.386 (8) |
Zn2—N4 | 2.191 (4) | C17—H17 | 0.93 |
Zn2—N5 | 2.095 (4) | C18—C19 | 1.369 (9) |
Zn2—N6 | 2.159 (4) | C18—H18 | 0.93 |
Zn2—Cl3 | 2.274 (2) | C19—C20 | 1.382 (10) |
Zn2—Cl4 | 2.273 (2) | C19—H19 | 0.93 |
O1w—H1w1 | 0.88 | C20—C21 | 1.380 (8) |
O1w—H1w2 | 0.87 | C20—H20 | 0.93 |
O2w—H2w1 | 0.85 | C21—H21 | 0.93 |
O2w—H2w2 | 0.88 | C22—C23 | 1.364 (8) |
N1—C5 | 1.335 (6) | C22—H22 | 0.93 |
N1—C1 | 1.348 (6) | C23—C24 | 1.378 (8) |
N2—C10 | 1.328 (6) | C23—H23 | 0.93 |
N2—C6 | 1.343 (6) | C24—C25 | 1.363 (7) |
N3—C15 | 1.331 (6) | C24—H24 | 0.93 |
N3—C11 | 1.346 (6) | C25—C26 | 1.398 (7) |
N4—C26 | 1.324 (6) | C25—H25 | 0.93 |
N4—C22 | 1.341 (6) | C26—C27 | 1.486 (6) |
N5—C31 | 1.331 (6) | C27—C28 | 1.371 (7) |
N5—C27 | 1.337 (6) | C28—C29 | 1.402 (6) |
N6—C36 | 1.339 (6) | C28—H28 | 0.93 |
N6—C32 | 1.343 (6) | C29—C30 | 1.403 (6) |
C1—C2 | 1.366 (7) | C29—C37 | 1.485 (7) |
C1—H1 | 0.93 | C30—C31 | 1.379 (7) |
C2—C3 | 1.360 (7) | C30—H30 | 0.93 |
C2—H2 | 0.93 | C31—C32 | 1.494 (6) |
C3—C4 | 1.382 (7) | C32—C33 | 1.378 (7) |
C3—H3 | 0.93 | C33—C34 | 1.374 (7) |
C4—C5 | 1.387 (7) | C33—H33 | 0.93 |
C4—H4 | 0.93 | C34—C35 | 1.368 (8) |
C5—C6 | 1.487 (7) | C34—H34 | 0.93 |
C6—C7 | 1.381 (7) | C35—C36 | 1.356 (7) |
C7—C8 | 1.391 (7) | C35—H35 | 0.93 |
C7—H7 | 0.93 | C36—H36 | 0.93 |
C8—C9 | 1.397 (7) | C37—C42 | 1.368 (7) |
C8—C16 | 1.486 (7) | C37—C38 | 1.385 (7) |
C9—C10 | 1.387 (7) | C38—C39 | 1.370 (8) |
C9—H9 | 0.93 | C38—H38 | 0.93 |
C10—C11 | 1.502 (7) | C39—C40 | 1.363 (9) |
C11—C12 | 1.371 (7) | C39—H39 | 0.93 |
C12—C13 | 1.385 (8) | C40—C41 | 1.378 (9) |
C12—H12 | 0.93 | C40—H40 | 0.93 |
C13—C14 | 1.369 (8) | C41—C42 | 1.382 (8) |
C13—H13 | 0.93 | C41—H41 | 0.93 |
C14—C15 | 1.379 (8) | C42—H42 | 0.93 |
N1—Zn1—N2 | 74.3 (2) | N3—C15—H15 | 118.5 |
N1—Zn1—N3 | 145.0 (2) | C14—C15—H15 | 118.5 |
N1—Zn1—Cl1 | 101.5 (1) | C21—C16—C17 | 118.7 (5) |
N1—Zn1—Cl2 | 98.9 (1) | C21—C16—C8 | 121.2 (5) |
N2—Zn1—N3 | 73.7 (2) | C17—C16—C8 | 120.1 (5) |
N2—Zn1—Cl1 | 105.8 (1) | C18—C17—C16 | 120.0 (6) |
N2—Zn1—Cl2 | 140.7 (1) | C18—C17—H17 | 120.0 |
N3—Zn1—Cl1 | 100.4 (1) | C16—C17—H17 | 120.0 |
N3—Zn1—Cl2 | 97.0 (1) | C19—C18—C17 | 120.9 (6) |
Cl1—Zn1—Cl2 | 113.5 (1) | C19—C18—H18 | 119.6 |
N4—Zn2—N5 | 74.1 (2) | C17—C18—H18 | 119.6 |
N4—Zn2—N6 | 148.1 (2) | C18—C19—C20 | 119.3 (6) |
N4—Zn2—Cl3 | 98.0 (1) | C18—C19—H19 | 120.4 |
N4—Zn2—Cl4 | 98.8 (1) | C20—C19—H19 | 120.4 |
N5—Zn2—N6 | 74.8 (2) | C21—C20—C19 | 121.1 (7) |
N5—Zn2—Cl3 | 114.9 (1) | C21—C20—H20 | 119.4 |
N5—Zn2—Cl4 | 134.9 (1) | C19—C20—H20 | 119.4 |
N6—Zn2—Cl3 | 101.2 (1) | C20—C21—C16 | 120.0 (6) |
N6—Zn2—Cl4 | 98.2 (1) | C20—C21—H21 | 120.0 |
Cl3—Zn2—Cl4 | 110.2 (1) | C16—C21—H21 | 120.0 |
H1w1—O1w—H1w2 | 104.0 | N4—C22—C23 | 123.2 (6) |
H2w1—O2w—H2w2 | 104.7 | N4—C22—H22 | 118.4 |
C5—N1—C1 | 118.7 (4) | C23—C22—H22 | 118.4 |
C5—N1—Zn1 | 116.8 (3) | C22—C23—C24 | 118.0 (5) |
C1—N1—Zn1 | 124.5 (3) | C22—C23—H23 | 121.0 |
C10—N2—C6 | 120.2 (4) | C24—C23—H23 | 121.0 |
C10—N2—Zn1 | 120.0 (3) | C25—C24—C23 | 119.9 (5) |
C6—N2—Zn1 | 118.5 (3) | C25—C24—H24 | 120.1 |
C15—N3—C11 | 118.5 (4) | C23—C24—H24 | 120.1 |
C15—N3—Zn1 | 124.4 (4) | C24—C25—C26 | 118.8 (5) |
C11—N3—Zn1 | 116.8 (3) | C24—C25—H25 | 120.6 |
C26—N4—C22 | 118.7 (5) | C26—C25—H25 | 120.6 |
C26—N4—Zn2 | 116.1 (3) | N4—C26—C25 | 121.4 (4) |
C22—N4—Zn2 | 124.6 (4) | N4—C26—C27 | 115.2 (4) |
C31—N5—C27 | 119.6 (4) | C25—C26—C27 | 123.3 (5) |
C31—N5—Zn2 | 120.3 (3) | N5—C27—C28 | 121.7 (4) |
C27—N5—Zn2 | 120.0 (3) | N5—C27—C26 | 113.5 (4) |
C36—N6—C32 | 118.2 (4) | C28—C27—C26 | 124.8 (4) |
C36—N6—Zn2 | 125.0 (4) | C27—C28—C29 | 120.1 (4) |
C32—N6—Zn2 | 116.7 (3) | C27—C28—H28 | 119.9 |
N1—C1—C2 | 122.6 (5) | C29—C28—H28 | 119.9 |
N1—C1—H1 | 118.7 | C28—C29—C30 | 117.1 (4) |
C2—C1—H1 | 118.7 | C28—C29—C37 | 121.3 (4) |
C3—C2—C1 | 118.7 (5) | C30—C29—C37 | 121.6 (4) |
C3—C2—H2 | 120.7 | C31—C30—C29 | 119.2 (4) |
C1—C2—H2 | 120.7 | C31—C30—H30 | 120.4 |
C2—C3—C4 | 120.1 (5) | C29—C30—H30 | 120.4 |
C2—C3—H3 | 119.9 | N5—C31—C30 | 122.4 (4) |
C4—C3—H3 | 119.9 | N5—C31—C32 | 113.3 (4) |
C3—C4—C5 | 118.3 (5) | C30—C31—C32 | 124.4 (4) |
C3—C4—H4 | 120.8 | N6—C32—C33 | 121.1 (4) |
C5—C4—H4 | 120.8 | N6—C32—C31 | 114.8 (4) |
N1—C5—C4 | 121.6 (4) | C33—C32—C31 | 124.0 (4) |
N1—C5—C6 | 114.2 (4) | C34—C33—C32 | 119.3 (5) |
C4—C5—C6 | 124.2 (4) | C34—C33—H33 | 120.4 |
N2—C6—C7 | 120.8 (5) | C32—C33—H33 | 120.4 |
N2—C6—C5 | 114.2 (4) | C35—C34—C33 | 119.6 (5) |
C7—C6—C5 | 125.0 (4) | C35—C34—H34 | 120.2 |
C6—C7—C8 | 120.5 (5) | C33—C34—H34 | 120.2 |
C6—C7—H7 | 119.8 | C36—C35—C34 | 118.3 (5) |
C8—C7—H7 | 119.8 | C36—C35—H35 | 120.9 |
C7—C8—C9 | 117.3 (4) | C34—C35—H35 | 120.9 |
C7—C8—C16 | 121.6 (5) | N6—C36—C35 | 123.6 (5) |
C9—C8—C16 | 121.0 (5) | N6—C36—H36 | 118.2 |
C10—C9—C8 | 119.5 (5) | C35—C36—H36 | 118.2 |
C10—C9—H9 | 120.3 | C42—C37—C38 | 118.0 (5) |
C8—C9—H9 | 120.3 | C42—C37—C29 | 121.1 (5) |
N2—C10—C9 | 121.8 (5) | C38—C37—C29 | 121.0 (5) |
N2—C10—C11 | 113.5 (4) | C39—C38—C37 | 121.0 (5) |
C9—C10—C11 | 124.7 (5) | C39—C38—H38 | 119.5 |
N3—C11—C12 | 121.6 (5) | C37—C38—H38 | 119.5 |
N3—C11—C10 | 113.7 (4) | C40—C39—C38 | 120.9 (6) |
C12—C11—C10 | 124.7 (5) | C40—C39—H39 | 119.5 |
C11—C12—C13 | 119.3 (5) | C38—C39—H39 | 119.5 |
C11—C12—H12 | 120.4 | C39—C40—C41 | 118.7 (6) |
C13—C12—H12 | 120.4 | C39—C40—H40 | 120.7 |
C14—C13—C12 | 119.3 (6) | C41—C40—H40 | 120.7 |
C14—C13—H13 | 120.4 | C40—C41—C42 | 120.5 (6) |
C12—C13—H13 | 120.4 | C40—C41—H41 | 119.8 |
C13—C14—C15 | 118.3 (5) | C42—C41—H41 | 119.8 |
C13—C14—H14 | 120.8 | C37—C42—C41 | 120.9 (6) |
C15—C14—H14 | 120.8 | C37—C42—H42 | 119.5 |
N3—C15—C14 | 122.9 (5) | C41—C42—H42 | 119.5 |
N2—Zn1—N1—C5 | −9.2 (3) | Zn1—N3—C11—C10 | −6.3 (6) |
N3—Zn1—N1—C5 | −33.7 (5) | N2—C10—C11—N3 | −5.2 (6) |
Cl2—Zn1—N1—C5 | −149.5 (3) | C9—C10—C11—N3 | 175.8 (5) |
Cl1—Zn1—N1—C5 | 94.2 (3) | N2—C10—C11—C12 | 175.3 (5) |
N2—Zn1—N1—C1 | 173.5 (5) | C9—C10—C11—C12 | −3.8 (8) |
N3—Zn1—N1—C1 | 149.1 (4) | N3—C11—C12—C13 | 1.0 (9) |
Cl2—Zn1—N1—C1 | 33.2 (4) | C10—C11—C12—C13 | −179.5 (5) |
Cl1—Zn1—N1—C1 | −83.1 (4) | C11—C12—C13—C14 | 1 (1) |
N1—Zn1—N2—C10 | −179.7 (4) | C12—C13—C14—C15 | −1 (1) |
N3—Zn1—N2—C10 | −14.1 (4) | C11—N3—C15—C14 | 0.8 (8) |
Cl2—Zn1—N2—C10 | −95.0 (4) | Zn1—N3—C15—C14 | −173.8 (4) |
Cl1—Zn1—N2—C10 | 82.4 (4) | C13—C14—C15—N3 | 0.7 (9) |
N1—Zn1—N2—C6 | 13.4 (3) | C7—C8—C16—C21 | 155.5 (5) |
N3—Zn1—N2—C6 | 179.0 (4) | C9—C8—C16—C21 | −24.0 (8) |
Cl2—Zn1—N2—C6 | 98.1 (4) | C7—C8—C16—C17 | −22.4 (8) |
Cl1—Zn1—N2—C6 | −84.5 (4) | C9—C8—C16—C17 | 158.1 (5) |
N2—Zn1—N3—C15 | −174.9 (5) | C21—C16—C17—C18 | 1.5 (8) |
N1—Zn1—N3—C15 | −150.3 (4) | C8—C16—C17—C18 | 179.5 (5) |
Cl2—Zn1—N3—C15 | −33.9 (4) | C16—C17—C18—C19 | −0.6 (9) |
Cl1—Zn1—N3—C15 | 81.5 (4) | C17—C18—C19—C20 | −1 (1) |
N2—Zn1—N3—C11 | 10.5 (3) | C18—C19—C20—C21 | 2 (1) |
N1—Zn1—N3—C11 | 35.0 (5) | C19—C20—C21—C16 | −1 (1) |
Cl2—Zn1—N3—C11 | 151.4 (3) | C17—C16—C21—C20 | −0.6 (9) |
Cl1—Zn1—N3—C11 | −93.1 (4) | C8—C16—C21—C20 | −178.5 (5) |
N5—Zn2—N4—C26 | 9.1 (4) | C26—N4—C22—C23 | 0.5 (9) |
N6—Zn2—N4—C26 | 22.1 (6) | Zn2—N4—C22—C23 | −169.9 (5) |
Cl4—Zn2—N4—C26 | 143.4 (4) | N4—C22—C23—C24 | 0 (1) |
Cl3—Zn2—N4—C26 | −104.5 (4) | C22—C23—C24—C25 | −1 (1) |
N5—Zn2—N4—C22 | 179.8 (5) | C23—C24—C25—C26 | 0.4 (9) |
N6—Zn2—N4—C22 | −167.3 (4) | C22—N4—C26—C25 | −0.7 (8) |
Cl4—Zn2—N4—C22 | −45.9 (5) | Zn2—N4—C26—C25 | 170.5 (4) |
Cl3—Zn2—N4—C22 | 66.1 (5) | C22—N4—C26—C27 | 179.7 (5) |
N6—Zn2—N5—C31 | 2.7 (4) | Zn2—N4—C26—C27 | −9.1 (6) |
N4—Zn2—N5—C31 | 175.7 (4) | C24—C25—C26—N4 | 0.3 (8) |
Cl4—Zn2—N5—C31 | 89.1 (4) | C24—C25—C26—C27 | 179.8 (5) |
Cl3—Zn2—N5—C31 | −92.7 (4) | C31—N5—C27—C28 | 1.0 (7) |
N6—Zn2—N5—C27 | 179.0 (4) | Zn2—N5—C27—C28 | −175.3 (4) |
N4—Zn2—N5—C27 | −8.0 (4) | C31—N5—C27—C26 | −177.7 (4) |
Cl4—Zn2—N5—C27 | −94.6 (4) | Zn2—N5—C27—C26 | 5.9 (6) |
Cl3—Zn2—N5—C27 | 83.6 (4) | N4—C26—C27—N5 | 2.5 (6) |
N5—Zn2—N6—C36 | 176.1 (5) | C25—C26—C27—N5 | −177.1 (5) |
N4—Zn2—N6—C36 | 163.2 (4) | N4—C26—C27—C28 | −176.3 (5) |
Cl4—Zn2—N6—C36 | 41.7 (5) | C25—C26—C27—C28 | 4.2 (8) |
Cl3—Zn2—N6—C36 | −70.9 (5) | N5—C27—C28—C29 | −0.6 (7) |
N5—Zn2—N6—C32 | −0.5 (4) | C26—C27—C28—C29 | 178.0 (5) |
N4—Zn2—N6—C32 | −13.4 (6) | C27—C28—C29—C30 | 0.0 (7) |
Cl4—Zn2—N6—C32 | −134.9 (4) | C27—C28—C29—C37 | −180.0 (5) |
Cl3—Zn2—N6—C32 | 112.5 (4) | C28—C29—C30—C31 | 0.1 (7) |
C5—N1—C1—C2 | −0.3 (8) | C37—C29—C30—C31 | −179.9 (4) |
Zn1—N1—C1—C2 | 176.9 (4) | C27—N5—C31—C30 | −0.9 (7) |
N1—C1—C2—C3 | −0.9 (9) | Zn2—N5—C31—C30 | 175.4 (4) |
C1—C2—C3—C4 | 1.9 (8) | C27—N5—C31—C32 | 179.5 (4) |
C2—C3—C4—C5 | −1.7 (8) | Zn2—N5—C31—C32 | −4.2 (6) |
C1—N1—C5—C4 | 0.5 (7) | C29—C30—C31—N5 | 0.3 (8) |
Zn1—N1—C5—C4 | −176.9 (4) | C29—C30—C31—C32 | 179.9 (4) |
C1—N1—C5—C6 | −178.2 (4) | C36—N6—C32—C33 | 0.3 (8) |
Zn1—N1—C5—C6 | 4.3 (5) | Zn2—N6—C32—C33 | 177.2 (4) |
C3—C4—C5—N1 | 0.5 (8) | C36—N6—C32—C31 | −178.3 (5) |
C3—C4—C5—C6 | 179.1 (5) | Zn2—N6—C32—C31 | −1.4 (6) |
C10—N2—C6—C7 | −2.6 (7) | N5—C31—C32—N6 | 3.5 (6) |
Zn1—N2—C6—C7 | 164.3 (4) | C30—C31—C32—N6 | −176.1 (5) |
C10—N2—C6—C5 | 177.7 (4) | N5—C31—C32—C33 | −175.0 (5) |
Zn1—N2—C6—C5 | −15.4 (5) | C30—C31—C32—C33 | 5.3 (8) |
N1—C5—C6—N2 | 6.8 (6) | N6—C32—C33—C34 | −0.9 (8) |
C4—C5—C6—N2 | −171.9 (5) | C31—C32—C33—C34 | 177.6 (5) |
N1—C5—C6—C7 | −172.8 (5) | C32—C33—C34—C35 | 0.9 (9) |
C4—C5—C6—C7 | 8.5 (8) | C33—C34—C35—C36 | −0.3 (9) |
N2—C6—C7—C8 | 2.2 (7) | C32—N6—C36—C35 | 0.3 (9) |
C5—C6—C7—C8 | −178.1 (4) | Zn2—N6—C36—C35 | −176.3 (4) |
C6—C7—C8—C9 | −0.1 (7) | C34—C35—C36—N6 | −0.3 (9) |
C6—C7—C8—C16 | −179.6 (5) | C28—C29—C37—C42 | 153.2 (5) |
C7—C8—C9—C10 | −1.6 (7) | C30—C29—C37—C42 | −26.8 (7) |
C16—C8—C9—C10 | 177.9 (5) | C28—C29—C37—C38 | −26.9 (7) |
C6—N2—C10—C9 | 0.9 (7) | C30—C29—C37—C38 | 153.1 (5) |
Zn1—N2—C10—C9 | −165.8 (4) | C42—C37—C38—C39 | −0.6 (8) |
C6—N2—C10—C11 | −178.2 (4) | C29—C37—C38—C39 | 179.5 (5) |
Zn1—N2—C10—C11 | 15.2 (6) | C37—C38—C39—C40 | 0.7 (9) |
C8—C9—C10—N2 | 1.2 (8) | C38—C39—C40—C41 | −1 (1) |
C8—C9—C10—C11 | −179.8 (5) | C39—C40—C41—C42 | 0.5 (9) |
C15—N3—C11—C12 | −1.7 (8) | C38—C37—C42—C41 | 0.5 (8) |
Zn1—N3—C11—C12 | 173.3 (4) | C29—C37—C42—C41 | −179.6 (5) |
C15—N3—C11—C10 | 178.7 (4) | C40—C41—C42—C37 | −0.4 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···Cl3 | 0.88 | 2.93 | 3.213 (6) | 101 |
O1w—H1w2···Cl4i | 0.87 | 2.49 | 3.297 (6) | 155 |
O2w—H2w1···Cl3 | 0.85 | 2.44 | 3.27 (2) | 167 |
O2w—H2w2···Cl4i | 0.88 | 2.37 | 3.23 (1) | 164 |
Symmetry code: (i) x−1, y, z. |