metal-organic compounds
[2-(2,2′-Bipyridin-6-yl-κ2N1,N1′)benzo[b][1,5]naphthyridine-κN1]dichloridozinc
aGraduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan
*Correspondence e-mail: ohtsu@sci.u-toyama.ac.jp
The coordination environment of the zinc(II) ion in the title complex, [ZnCl2(C22H14N4)], is distorted trigonal–bipyramidal comprised by three N atoms from the 2-([2,2′-bipyridin]-6-yl)benzo[b][1,5]naphthyridine ligand and two Cl− ions. In the crystal, neighbouring molecules are connected by π–π stacking interactions along the a-axis direction.
Keywords: crystal structure; zinc(II) complex; NAD+/NADH-analogous ligand.
CCDC reference: 1511041
Structure description
In order to gain valuable insights into the nature of the nicotinamide adenine dinucleotide (NAD) function and to develop photorenewable hydride reagents utilizing the NAD+/NADH redox function in NAD, we have so far investigated transition-metal complexes having NAD+/NADH-analogous ligands (Fukushima et al., 2010; Ohtsu & Tanaka, 2012a,b; Ohtsu et al., 2015, 2016). In this paper, a new zinc complex having a new NAD+/NADH-analogous ligand bbn (bbn = 2-([2,2′-bipyridin]-6-yl)benzo[b][1,5]naphthyridine) has been synthesized and structurally characterized.
The molecular structure of the title complex, [Zn(bbn)Cl2], is shown in Fig. 1. The zinc(II) ion is surrounded by three N atoms from the bbn ligand and two Cl− ions. The bond lengths from the zinc to each of donor N atoms and chloride are Zn1—N1 = 2.191 (2), Zn1—N2 = 2.085 (2), Zn1—N3 = 2.230 (2), Zn1—Cl1 = 2.2732 (7) and Zn1—Cl2 = 2.2504 (7) Å. A range of five-coordinate geometries varying from trigonal–bipyramidal to square–pyramidal can be indicated by the τ parameter ranging from τ = 1 for an ideal trigonal–bipyramidal geometry to τ = 0 for an ideal square–pyramidal geometry (Addison et al., 1984). The τ value for the zinc(II) ion in the title complex is obtained as τ = 0.44 by using the equation τ = (β − α)/60 (Addison et al., 1984), where α = N2—Zn1—Cl2 [123.76 (6)°], β = N1—Zn1—N3 [150.24 (8)°]. In spite of the τ value of 0.44, the coordination environment of the zinc(II) ion in [Zn(bbn)Cl2] can be better described as distorted trigonal–bipyramidal.
This title complex presents intermolecular π–π stacking interactions along the a-axis direction as shown in Fig. 2. The distances between the centroids of rings A (C14–17/C21/C22) and B (N1/C1–5)i [symmetry code: (i) + x, − y, − + z], and between the centroids of the rings C (N3/C11–13/C19/C20) and D (N1/C1–5)ii [symmetry code: (ii) − x, + y, − z] are 3.5513 (3) and 3.5237 (3) Å, respectively.
Synthesis and crystallization
The bbn ligand was prepared in the same manner as that for the synthesis of pbn (Koizumi & Tanaka, 2005) using 6-acetyl-2,2′-bipyridine (Vlugt et al., 2008) instead of 2-acetyl-pyridine. 1H NMR (300 MHz, CDCl3): 9.13 (d, 1H), 9.10 (s, 1H), 8.79 (dd, 1H), 8.75–8.65 (m, 3H), 8.57 (dd, 1H), 8.29 (dd, 1H), 8.14 (dt, 1H), 8.07 (t, 1H), 7.96–7.82 (m, 2H), 7.63 (ddd, 1H), 7.38 (ddd, 1H).
To an acetonitrile solution (4 ml) of ZnCl2 (20.4 mg, 0.15 mmol) was added dropwise bbn (50.0 mg, 0.15 mmol) in dichloromethane (4 ml). The resulting yellow precipitate was filtered and dissolved in hot methanol for recrystallization. After the solution was left to stand for a few weeks at room temperature, yellow crystals of the title complex [Zn(bbn)Cl2] were obtained (yield; 18.2 mg, 25.6%). Elemental analysis, found: C 55.82, H 2.99, N 11.71%; calculated for C22H14Cl2N4Zn: C 56.14, H 3.00, N 11.90%.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1511041
https://doi.org/10.1107/S241431461601779X/bt4032sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461601779X/bt4032Isup2.hkl
Data collection: RAPID-AUTO (Rigaku, 2001); cell
RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: CrystalStructure (Rigaku, 2016), Mercury (Macrae et al., 2008) and CrystalMaker (Palmer, 2007); software used to prepare material for publication: CrystalStructure (Rigaku, 2016) and publCIF (Westrip, 2010).[ZnCl2(C22H14N4)] | F(000) = 952.00 |
Mr = 470.67 | Dx = 1.620 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
a = 10.8040 (2) Å | Cell parameters from 16370 reflections |
b = 13.6433 (3) Å | θ = 3.0–27.4° |
c = 13.2159 (3) Å | µ = 1.57 mm−1 |
β = 97.8812 (7)° | T = 173 K |
V = 1929.65 (7) Å3 | Block, yellow |
Z = 4 | 0.08 × 0.08 × 0.07 mm |
Rigaku R-AXIS RAPID diffractometer | 4050 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→14 |
Tmin = 0.718, Tmax = 0.896 | k = −17→17 |
18736 measured reflections | l = −16→17 |
4400 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0424P)2 + 2.004P] where P = (Fo2 + 2Fc2)/3 |
4400 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
Primary atom site location: structure-invariant direct methods |
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. |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
ZN1 | 0.14600 (3) | 0.22246 (2) | 0.60516 (2) | 0.02931 (10) | |
CL1 | 0.35323 (6) | 0.19462 (5) | 0.60386 (5) | 0.04174 (16) | |
CL2 | 0.00807 (7) | 0.17449 (5) | 0.47109 (5) | 0.03958 (16) | |
N1 | 0.10596 (19) | 0.10447 (16) | 0.70834 (14) | 0.0311 (4) | |
N2 | 0.09581 (19) | 0.29423 (16) | 0.73276 (16) | 0.0323 (4) | |
N3 | 0.15042 (19) | 0.38149 (15) | 0.56697 (16) | 0.0317 (4) | |
N4 | 0.2032 (2) | 0.56306 (16) | 0.3716 (2) | 0.0424 (5) | |
C1 | 0.1099 (2) | 0.00880 (19) | 0.68850 (19) | 0.0342 (5) | |
H1 | 0.132729 | −0.011245 | 0.624729 | 0.041* | |
C2 | 0.0824 (3) | −0.0629 (2) | 0.7564 (2) | 0.0387 (6) | |
H2 | 0.087495 | −0.130494 | 0.740161 | 0.046* | |
C3 | 0.0476 (3) | −0.0333 (2) | 0.8480 (2) | 0.0423 (6) | |
H3 | 0.028589 | −0.080493 | 0.896416 | 0.051* | |
C4 | 0.0406 (3) | 0.0652 (2) | 0.86885 (19) | 0.0406 (6) | |
H4 | 0.014766 | 0.086496 | 0.931137 | 0.049* | |
C5 | 0.0715 (2) | 0.1336 (2) | 0.79818 (18) | 0.0324 (5) | |
C6 | 0.0691 (2) | 0.2413 (2) | 0.81226 (19) | 0.0351 (5) | |
C7 | 0.0414 (3) | 0.2863 (2) | 0.9013 (2) | 0.0470 (7) | |
H7 | 0.021399 | 0.248685 | 0.957327 | 0.056* | |
C8 | 0.0440 (3) | 0.3871 (3) | 0.9053 (2) | 0.0526 (8) | |
H8 | 0.026562 | 0.419459 | 0.965325 | 0.063* | |
C9 | 0.0717 (3) | 0.4421 (2) | 0.8232 (2) | 0.0454 (7) | |
H9 | 0.073696 | 0.511692 | 0.826419 | 0.055* | |
C10 | 0.0967 (2) | 0.3928 (2) | 0.7355 (2) | 0.0358 (5) | |
C11 | 0.1253 (2) | 0.44115 (18) | 0.6410 (2) | 0.0341 (5) | |
C12 | 0.1246 (2) | 0.54527 (19) | 0.6295 (2) | 0.0386 (6) | |
H12 | 0.105882 | 0.586341 | 0.683423 | 0.046* | |
C13 | 0.1508 (2) | 0.58476 (19) | 0.5410 (2) | 0.0418 (6) | |
H13 | 0.150643 | 0.653960 | 0.533003 | 0.050* | |
C14 | 0.2521 (3) | 0.5421 (2) | 0.2008 (3) | 0.0526 (8) | |
H14 | 0.254409 | 0.611196 | 0.192511 | 0.063* | |
C15 | 0.2746 (3) | 0.4838 (3) | 0.1234 (2) | 0.0535 (8) | |
H15 | 0.294094 | 0.512598 | 0.062067 | 0.064* | |
C16 | 0.2700 (3) | 0.3804 (3) | 0.1316 (2) | 0.0472 (7) | |
H16 | 0.285278 | 0.340550 | 0.075634 | 0.057* | |
C17 | 0.2437 (3) | 0.3380 (2) | 0.2195 (2) | 0.0427 (6) | |
H17 | 0.240144 | 0.268636 | 0.224379 | 0.051* | |
C18 | 0.1986 (2) | 0.35777 (18) | 0.3966 (2) | 0.0350 (5) | |
H18 | 0.197990 | 0.288697 | 0.405575 | 0.042* | |
C19 | 0.1787 (2) | 0.52359 (18) | 0.4595 (2) | 0.0353 (5) | |
C20 | 0.1766 (2) | 0.41966 (17) | 0.47647 (19) | 0.0316 (5) | |
C21 | 0.2247 (2) | 0.5025 (2) | 0.2952 (2) | 0.0386 (6) | |
C22 | 0.2214 (2) | 0.39714 (19) | 0.3045 (2) | 0.0348 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
ZN1 | 0.03447 (16) | 0.02843 (15) | 0.02587 (15) | 0.00193 (10) | 0.00711 (11) | −0.00438 (10) |
CL1 | 0.0385 (3) | 0.0367 (3) | 0.0536 (4) | 0.0085 (3) | 0.0192 (3) | 0.0075 (3) |
CL2 | 0.0525 (4) | 0.0360 (3) | 0.0293 (3) | −0.0078 (3) | 0.0021 (3) | −0.0062 (2) |
N1 | 0.0297 (10) | 0.0408 (11) | 0.0230 (9) | −0.0008 (8) | 0.0043 (7) | −0.0005 (8) |
N2 | 0.0292 (10) | 0.0378 (11) | 0.0296 (10) | 0.0037 (8) | 0.0033 (8) | −0.0088 (8) |
N3 | 0.0298 (10) | 0.0284 (10) | 0.0359 (11) | 0.0027 (8) | 0.0002 (8) | −0.0058 (8) |
N4 | 0.0390 (12) | 0.0280 (11) | 0.0578 (15) | −0.0030 (9) | −0.0022 (10) | 0.0031 (10) |
C1 | 0.0352 (12) | 0.0379 (13) | 0.0290 (12) | −0.0033 (10) | 0.0026 (9) | −0.0006 (10) |
C2 | 0.0384 (14) | 0.0403 (14) | 0.0357 (14) | −0.0071 (11) | −0.0011 (10) | 0.0032 (11) |
C3 | 0.0415 (14) | 0.0531 (17) | 0.0317 (13) | −0.0083 (12) | 0.0026 (10) | 0.0098 (11) |
C4 | 0.0361 (13) | 0.0625 (18) | 0.0241 (12) | −0.0003 (12) | 0.0069 (10) | 0.0024 (11) |
C5 | 0.0267 (11) | 0.0448 (14) | 0.0257 (11) | 0.0016 (10) | 0.0035 (9) | −0.0021 (10) |
C6 | 0.0287 (12) | 0.0499 (15) | 0.0269 (12) | 0.0038 (11) | 0.0048 (9) | −0.0052 (10) |
C7 | 0.0525 (17) | 0.0563 (18) | 0.0343 (14) | 0.0067 (14) | 0.0137 (12) | −0.0090 (12) |
C8 | 0.0576 (18) | 0.060 (2) | 0.0421 (16) | 0.0051 (15) | 0.0148 (13) | −0.0171 (14) |
C9 | 0.0438 (15) | 0.0411 (15) | 0.0510 (17) | 0.0050 (12) | 0.0050 (12) | −0.0175 (12) |
C10 | 0.0264 (11) | 0.0411 (14) | 0.0387 (13) | 0.0036 (10) | 0.0000 (9) | −0.0122 (11) |
C11 | 0.0256 (11) | 0.0310 (12) | 0.0436 (14) | 0.0036 (9) | −0.0022 (10) | −0.0113 (10) |
C12 | 0.0314 (12) | 0.0314 (13) | 0.0514 (16) | 0.0028 (10) | 0.0002 (11) | −0.0121 (11) |
C13 | 0.0339 (13) | 0.0226 (11) | 0.0650 (18) | 0.0028 (10) | −0.0066 (12) | −0.0071 (11) |
C14 | 0.0563 (18) | 0.0423 (16) | 0.0577 (19) | −0.0096 (14) | 0.0032 (14) | 0.0151 (14) |
C15 | 0.0502 (17) | 0.064 (2) | 0.0461 (17) | −0.0095 (15) | 0.0075 (13) | 0.0184 (15) |
C16 | 0.0427 (15) | 0.0589 (18) | 0.0408 (15) | −0.0016 (13) | 0.0088 (12) | 0.0064 (13) |
C17 | 0.0460 (15) | 0.0411 (15) | 0.0418 (15) | 0.0001 (12) | 0.0088 (12) | 0.0061 (11) |
C18 | 0.0372 (13) | 0.0260 (11) | 0.0413 (14) | 0.0007 (10) | 0.0043 (10) | −0.0002 (10) |
C19 | 0.0273 (11) | 0.0254 (11) | 0.0508 (15) | −0.0013 (9) | −0.0036 (10) | 0.0013 (10) |
C20 | 0.0254 (11) | 0.0263 (11) | 0.0414 (13) | 0.0010 (9) | −0.0017 (9) | 0.0002 (9) |
C21 | 0.0297 (12) | 0.0361 (13) | 0.0479 (15) | −0.0039 (10) | −0.0020 (10) | 0.0076 (11) |
C22 | 0.0297 (12) | 0.0329 (13) | 0.0411 (14) | 0.0000 (10) | 0.0018 (10) | 0.0053 (10) |
ZN1—N2 | 2.085 (2) | C8—C9 | 1.385 (5) |
ZN1—N1 | 2.191 (2) | C8—H8 | 0.9500 |
ZN1—N3 | 2.230 (2) | C9—C10 | 1.398 (4) |
ZN1—CL2 | 2.2504 (7) | C9—H9 | 0.9500 |
ZN1—CL1 | 2.2732 (7) | C10—C11 | 1.482 (4) |
N1—C1 | 1.333 (3) | C11—C12 | 1.429 (4) |
N1—C5 | 1.352 (3) | C12—C13 | 1.352 (4) |
N2—C6 | 1.339 (3) | C12—H12 | 0.9500 |
N2—C10 | 1.345 (3) | C13—C19 | 1.427 (4) |
N3—C11 | 1.329 (3) | C13—H13 | 0.9500 |
N3—C20 | 1.369 (3) | C14—C15 | 1.344 (5) |
N4—C19 | 1.340 (4) | C14—C21 | 1.427 (4) |
N4—C21 | 1.349 (4) | C14—H14 | 0.9500 |
C1—C2 | 1.387 (4) | C15—C16 | 1.417 (5) |
C1—H1 | 0.9500 | C15—H15 | 0.9500 |
C2—C3 | 1.377 (4) | C16—C17 | 1.363 (4) |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C3—C4 | 1.377 (4) | C17—C22 | 1.430 (4) |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.393 (4) | C18—C22 | 1.383 (4) |
C4—H4 | 0.9500 | C18—C20 | 1.397 (4) |
C5—C6 | 1.481 (4) | C18—H18 | 0.9500 |
C6—C7 | 1.396 (4) | C19—C20 | 1.436 (3) |
C7—C8 | 1.375 (5) | C21—C22 | 1.444 (4) |
C7—H7 | 0.9500 | ||
N2—ZN1—N1 | 75.30 (8) | C9—C8—H8 | 119.4 |
N2—ZN1—N3 | 75.05 (8) | C8—C9—C10 | 118.3 (3) |
N1—ZN1—N3 | 150.24 (8) | C8—C9—H9 | 120.8 |
N2—ZN1—CL2 | 123.76 (6) | C10—C9—H9 | 120.8 |
N1—ZN1—CL2 | 96.34 (6) | N2—C10—C9 | 120.1 (3) |
N3—ZN1—CL2 | 97.88 (5) | N2—C10—C11 | 115.1 (2) |
N2—ZN1—CL1 | 116.76 (6) | C9—C10—C11 | 124.8 (3) |
N1—ZN1—CL1 | 99.25 (6) | N3—C11—C12 | 122.0 (3) |
N3—ZN1—CL1 | 96.27 (6) | N3—C11—C10 | 115.8 (2) |
CL2—ZN1—CL1 | 119.48 (3) | C12—C11—C10 | 122.2 (2) |
C1—N1—C5 | 118.7 (2) | C13—C12—C11 | 119.3 (3) |
C1—N1—ZN1 | 125.63 (16) | C13—C12—H12 | 120.4 |
C5—N1—ZN1 | 115.62 (17) | C11—C12—H12 | 120.4 |
C6—N2—C10 | 121.3 (2) | C12—C13—C19 | 120.7 (2) |
C6—N2—ZN1 | 119.28 (17) | C12—C13—H13 | 119.6 |
C10—N2—ZN1 | 119.31 (18) | C19—C13—H13 | 119.6 |
C11—N3—C20 | 119.8 (2) | C15—C14—C21 | 121.5 (3) |
C11—N3—ZN1 | 114.62 (18) | C15—C14—H14 | 119.2 |
C20—N3—ZN1 | 125.54 (16) | C21—C14—H14 | 119.2 |
C19—N4—C21 | 118.5 (2) | C14—C15—C16 | 121.3 (3) |
N1—C1—C2 | 123.2 (2) | C14—C15—H15 | 119.4 |
N1—C1—H1 | 118.4 | C16—C15—H15 | 119.4 |
C2—C1—H1 | 118.4 | C17—C16—C15 | 120.1 (3) |
C3—C2—C1 | 118.1 (3) | C17—C16—H16 | 120.0 |
C3—C2—H2 | 121.0 | C15—C16—H16 | 120.0 |
C1—C2—H2 | 121.0 | C16—C17—C22 | 120.5 (3) |
C4—C3—C2 | 119.5 (3) | C16—C17—H17 | 119.7 |
C4—C3—H3 | 120.3 | C22—C17—H17 | 119.7 |
C2—C3—H3 | 120.3 | C22—C18—C20 | 120.0 (2) |
C3—C4—C5 | 119.7 (2) | C22—C18—H18 | 120.0 |
C3—C4—H4 | 120.2 | C20—C18—H18 | 120.0 |
C5—C4—H4 | 120.2 | N4—C19—C13 | 120.5 (2) |
N1—C5—C4 | 120.8 (2) | N4—C19—C20 | 122.8 (2) |
N1—C5—C6 | 114.4 (2) | C13—C19—C20 | 116.7 (2) |
C4—C5—C6 | 124.8 (2) | N3—C20—C18 | 120.5 (2) |
N2—C6—C7 | 121.2 (3) | N3—C20—C19 | 121.4 (2) |
N2—C6—C5 | 115.3 (2) | C18—C20—C19 | 118.1 (2) |
C7—C6—C5 | 123.5 (3) | N4—C21—C14 | 120.0 (3) |
C8—C7—C6 | 117.8 (3) | N4—C21—C22 | 122.5 (2) |
C8—C7—H7 | 121.1 | C14—C21—C22 | 117.5 (3) |
C6—C7—H7 | 121.1 | C18—C22—C17 | 122.8 (2) |
C7—C8—C9 | 121.2 (3) | C18—C22—C21 | 118.1 (2) |
C7—C8—H8 | 119.4 | C17—C22—C21 | 119.1 (2) |
C5—N1—C1—C2 | −1.1 (4) | N2—C10—C11—C12 | 177.2 (2) |
ZN1—N1—C1—C2 | −179.35 (19) | C9—C10—C11—C12 | −2.8 (4) |
N1—C1—C2—C3 | 1.0 (4) | N3—C11—C12—C13 | −0.3 (4) |
C1—C2—C3—C4 | 0.4 (4) | C10—C11—C12—C13 | −179.6 (2) |
C2—C3—C4—C5 | −1.5 (4) | C11—C12—C13—C19 | 0.2 (4) |
C1—N1—C5—C4 | 0.0 (3) | C21—C14—C15—C16 | 1.1 (5) |
ZN1—N1—C5—C4 | 178.34 (19) | C14—C15—C16—C17 | −0.8 (5) |
C1—N1—C5—C6 | −179.5 (2) | C15—C16—C17—C22 | −0.4 (5) |
ZN1—N1—C5—C6 | −1.2 (3) | C21—N4—C19—C13 | −177.6 (2) |
C3—C4—C5—N1 | 1.3 (4) | C21—N4—C19—C20 | 1.3 (4) |
C3—C4—C5—C6 | −179.2 (2) | C12—C13—C19—N4 | 179.3 (2) |
C10—N2—C6—C7 | −0.1 (4) | C12—C13—C19—C20 | 0.3 (4) |
ZN1—N2—C6—C7 | 176.6 (2) | C11—N3—C20—C18 | −177.6 (2) |
C10—N2—C6—C5 | 179.9 (2) | ZN1—N3—C20—C18 | 2.6 (3) |
ZN1—N2—C6—C5 | −3.3 (3) | C11—N3—C20—C19 | 0.5 (3) |
N1—C5—C6—N2 | 2.9 (3) | ZN1—N3—C20—C19 | −179.22 (17) |
C4—C5—C6—N2 | −176.6 (2) | C22—C18—C20—N3 | 178.1 (2) |
N1—C5—C6—C7 | −177.1 (3) | C22—C18—C20—C19 | −0.1 (4) |
C4—C5—C6—C7 | 3.4 (4) | N4—C19—C20—N3 | −179.6 (2) |
N2—C6—C7—C8 | −0.9 (4) | C13—C19—C20—N3 | −0.7 (3) |
C5—C6—C7—C8 | 179.1 (3) | N4—C19—C20—C18 | −1.4 (4) |
C6—C7—C8—C9 | 0.8 (5) | C13—C19—C20—C18 | 177.5 (2) |
C7—C8—C9—C10 | 0.2 (5) | C19—N4—C21—C14 | −179.5 (2) |
C6—N2—C10—C9 | 1.2 (4) | C19—N4—C21—C22 | 0.3 (4) |
ZN1—N2—C10—C9 | −175.60 (19) | C15—C14—C21—N4 | 179.6 (3) |
C6—N2—C10—C11 | −178.8 (2) | C15—C14—C21—C22 | −0.3 (4) |
ZN1—N2—C10—C11 | 4.5 (3) | C20—C18—C22—C17 | −179.5 (2) |
C8—C9—C10—N2 | −1.2 (4) | C20—C18—C22—C21 | 1.6 (4) |
C8—C9—C10—C11 | 178.7 (3) | C16—C17—C22—C18 | −177.7 (3) |
C20—N3—C11—C12 | 0.0 (3) | C16—C17—C22—C21 | 1.2 (4) |
ZN1—N3—C11—C12 | 179.77 (18) | N4—C21—C22—C18 | −1.8 (4) |
C20—N3—C11—C10 | 179.3 (2) | C14—C21—C22—C18 | 178.1 (3) |
ZN1—N3—C11—C10 | −0.9 (3) | N4—C21—C22—C17 | 179.3 (2) |
N2—C10—C11—N3 | −2.2 (3) | C14—C21—C22—C17 | −0.9 (4) |
C9—C10—C11—N3 | 177.9 (2) |
Acknowledgements
This work was supported in part by Grant-in-Aids for Scientific Research C (No. 25410067) from the Japan Society for the Promotion of Science (JSPS) and the Ministry of Education, Culture, Sports, Science, and Technology of Japan (MEXT).
References
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356. CSD CrossRef Web of Science Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Mallamo, M., Mazzone, A., Polidori, G. & Spagna, R. (2012). J. Appl. Cryst. 45, 357–361. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fukushima, T., Wada, T., Ohtsu, H. & Tanaka, K. (2010). Dalton Trans. 39, 11526–11534. Web of Science CSD CrossRef CAS PubMed Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Koizumi, T.-a. & Tanaka, K. (2005). Angew. Chem. Int. Ed. 44, 5891–5894. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ohtsu, H., Fujii, S., Tsuge, K. & Tanaka, K. (2016). Dalton Trans. 45, 16130–16133. Web of Science CSD CrossRef CAS Google Scholar
Ohtsu, H. & Tanaka, K. (2012a). Chem. Commun. 48, 1796–1798. Web of Science CSD CrossRef CAS Google Scholar
Ohtsu, H. & Tanaka, K. (2012b). Angew. Chem. Int. Ed. 51, 9792–9795. Web of Science CrossRef CAS Google Scholar
Ohtsu, H., Tsuge, K. & Tanaka, K. (2015). J. Photochem. Photobiol. Chem. 313, 163–167. Web of Science CrossRef CAS Google Scholar
Palmer, D. (2007). CrystalMaker. Crystal Maker, Bicester, England. Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2016). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Vlugt, J. I. van der, Demeshko, S., Dechert, S. & Meyer, F. (2008). Inorg. Chem. 47, 1576–1585. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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