metal-organic compounds
Bis[2,3-bis(pyridin-2-yl)pyrazine-κ2N2,N3]palladium(II) dinitrate acetonitrile monosolvate
aChonnam National University, School of Chemical Engineering, Research Institute of Catalysis, Gwangju, Republic of Korea
*Correspondence e-mail: hakwang@chonnam.ac.kr
The title compound, [Pd(C14H10N4)2](NO3)2·CH3CN, consists of a cationic PdII complex, two anions and one lattice solvent molecule, all in general positions. In the complex, the PdII cation is four-coordinated in a slightly distorted square-planar geometry defined by the four N atoms of two bidentate 2,3-di-2-pyridylpyrazine ligands. The complex, anions and solvent molecule are linked by weak C—H⋯O intermolecular hydrogen bonds. In the crystal, the complex molecules are stacked in columns along the a axis.
Keywords: crystal structure; palladium(II) complex; square-planar structure; 2,3-di-2-pyridylpyrazine.
CCDC reference: 2062092
Structure description
With reference to the title compound, [Pd(dpp)2](NO3)2·CH3CN (dpp = 2,3-di-2-pyridylpyrazine), the crystal structures of related dpp-PdII complexes [PdX2(dpp)] have been determined previously [X = Cl (Ha, 2011a,b); X = Br (Ha, 2011c); X = I (Ha, 2011d); X = SCN (Ha, 2012)], and a heterometallic complex has been also reported, namely [Ru(bipy)2(μ2-dpp)PdCl2](PF6)2, where bipy is 2,2′-bipyridine (Yam et al., 1994).
The title compound consists of a cationic PdII complex [Pd(dpp)2]2+, two NO3− anions and one solvent CH3CN molecule (Fig. 1). In the complex, the central PdII cation is four-coordinated in a slightly distorted square-planar geometry defined by the pyridyl N3, N4, N7 and N8 atoms of the two bidentate dpp ligands. The tight N—Pd—N chelating angles of N3—Pd1—N4 = 86.99 (7)° and N7—Pd1—N8 = 85.98 (7)° contribute to the distortion of the square-plane. The Pd—N bond lengths are almost equal [2.0170 (18) to 2.0286 (19) Å]. In the crystal, the pyridine rings are considerably inclined to the least-squares plane of the [PdN4] unit [maximum deviation = 0.0204 (7) Å], with dihedral angles of 70.56 (7) (ring N3⋯C9), 67.63 (6) (ring N4⋯C14), 71.32 (6) (ring N7⋯C23) and 71.64 (7)° (ring N8⋯C28). The nearly planar pyrazine rings [maximum deviation = 0.027 (2) Å] are fairly perpendicular to the [PdN4] unit plane, with dihedral angles of 82.07 (7) (ring N1⋯C4) and 84.20 (7)° (ring N5⋯C18).
In the ), the complex, anions and solvent molecules form intermolecular weak C—H⋯O hydrogen bonds (Table 1). The complex molecules are stacked in columns along the a axis. In the columns, numerous intra- and intermolecular π–π interactions between adjacent six-membered rings are present. For Cg1 (the centroid of ring N4⋯C14) and Cg1i [symmetry code: (i) −x + 2, −y + 2, −z + 1), the centroid-to-centroid separation is 3.688 (2) Å and the planes are parallel and shifted by 1.683 Å.
(Fig. 2Synthesis and crystallization
To a solution of 2,3-di-2-pyridylpyrazine (0.303 g, 1.293 mmol) in acetone (30 ml) was added Pd(NO3)2·2H2O (0.170 g, 0.637 mmol) and stirred for 1 h at room temperature. The formed precipitate was recrystallized from MeOH/ether, washed with ether, and dried under vacuum, to give a white powder (0.378 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of a MeOH/CH3CN solution, at room temperature.
Refinement
Crystal data, data collection and structure . The highest peak (0.89 e Å−3) and the deepest hole (−0.49 e Å−3) in the last difference-Fourier map are located 1.02 and 0.97 Å, respectively, from atom O3.
details are summarized in Table 2
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Structural data
CCDC reference: 2062092
https://doi.org/10.1107/S241431462100153X/bh4059sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462100153X/bh4059Isup2.hkl
Data collection: APEX2 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/7 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).[Pd(C14H10N4)2](NO3)2·C2H3N | Z = 2 |
Mr = 739.99 | F(000) = 748 |
Triclinic, P1 | Dx = 1.655 Mg m−3 |
a = 10.2013 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6159 (5) Å | Cell parameters from 9802 reflections |
c = 14.2762 (6) Å | θ = 2.3–28.3° |
α = 90.9753 (16)° | µ = 0.69 mm−1 |
β = 109.2479 (14)° | T = 223 K |
γ = 109.9435 (14)° | Block, colorless |
V = 1485.28 (11) Å3 | 0.22 × 0.15 × 0.09 mm |
Bruker APEX2, PHOTON 100 detector diffractometer | 5399 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.032 |
φ and ω scans | θmax = 26.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −12→12 |
Tmin = 0.699, Tmax = 0.745 | k = −14→14 |
38859 measured reflections | l = −17→17 |
5889 independent reflections |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.030P)2 + 1.3932P] where P = (Fo2 + 2Fc2)/3 |
5889 reflections | (Δ/σ)max = 0.001 |
434 parameters | Δρmax = 0.89 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Refinement. Hydrogen atoms bonded to C atoms were positioned geometrically and allowed to ride on their parent atoms: C—H = 0.94 or 0.97 Å, with isotropic displacements Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). |
x | y | z | Uiso*/Ueq | ||
Pd1 | 0.85573 (2) | 0.80002 (2) | 0.21420 (2) | 0.02031 (6) | |
N1 | 0.8010 (2) | 0.47002 (17) | 0.32663 (14) | 0.0296 (4) | |
N2 | 1.1007 (2) | 0.62333 (18) | 0.41615 (14) | 0.0300 (4) | |
N3 | 0.70063 (19) | 0.72337 (16) | 0.27734 (14) | 0.0243 (4) | |
N4 | 1.00126 (19) | 0.87763 (16) | 0.35473 (13) | 0.0226 (4) | |
N5 | 0.8194 (2) | 0.46396 (17) | 0.07565 (15) | 0.0318 (4) | |
N6 | 1.1185 (2) | 0.61800 (19) | 0.15483 (15) | 0.0316 (4) | |
N7 | 0.71597 (19) | 0.71968 (16) | 0.07375 (13) | 0.0249 (4) | |
N8 | 1.01151 (19) | 0.87359 (16) | 0.15207 (13) | 0.0243 (4) | |
C1 | 0.8420 (2) | 0.59294 (19) | 0.34974 (15) | 0.0228 (4) | |
C2 | 0.9924 (2) | 0.6705 (2) | 0.39218 (15) | 0.0232 (4) | |
C3 | 1.0584 (3) | 0.5018 (2) | 0.39210 (18) | 0.0342 (5) | |
H3 | 1.1317 | 0.4662 | 0.4075 | 0.041* | |
C4 | 0.9105 (3) | 0.4261 (2) | 0.34529 (18) | 0.0336 (5) | |
H4 | 0.8864 | 0.3415 | 0.3261 | 0.040* | |
C5 | 0.7133 (2) | 0.6331 (2) | 0.33404 (16) | 0.0259 (5) | |
C6 | 0.6064 (3) | 0.5744 (2) | 0.3748 (2) | 0.0380 (6) | |
H6 | 0.6146 | 0.5096 | 0.4121 | 0.046* | |
C7 | 0.4865 (3) | 0.6125 (3) | 0.3599 (2) | 0.0478 (7) | |
H7 | 0.4132 | 0.5743 | 0.3874 | 0.057* | |
C8 | 0.4767 (3) | 0.7063 (3) | 0.3047 (2) | 0.0470 (7) | |
H8 | 0.3977 | 0.7344 | 0.2950 | 0.056* | |
C9 | 0.5843 (2) | 0.7592 (2) | 0.2632 (2) | 0.0350 (6) | |
H9 | 0.5757 | 0.8223 | 0.2239 | 0.042* | |
C10 | 1.0482 (2) | 0.8070 (2) | 0.42188 (16) | 0.0233 (4) | |
C11 | 1.1519 (2) | 0.8600 (2) | 0.51676 (17) | 0.0308 (5) | |
H11 | 1.1821 | 0.8097 | 0.5635 | 0.037* | |
C12 | 1.2106 (3) | 0.9870 (2) | 0.54251 (19) | 0.0364 (6) | |
H12 | 1.2824 | 1.0240 | 0.6064 | 0.044* | |
C13 | 1.1629 (3) | 1.0586 (2) | 0.47366 (19) | 0.0342 (5) | |
H13 | 1.2022 | 1.1453 | 0.4895 | 0.041* | |
C14 | 1.0563 (2) | 1.0014 (2) | 0.38061 (18) | 0.0287 (5) | |
H14 | 1.0213 | 1.0503 | 0.3342 | 0.034* | |
C15 | 0.8605 (2) | 0.58748 (19) | 0.07894 (15) | 0.0237 (4) | |
C16 | 1.0115 (2) | 0.6651 (2) | 0.11952 (15) | 0.0238 (4) | |
C17 | 1.0748 (3) | 0.4960 (2) | 0.15386 (19) | 0.0367 (6) | |
H17 | 1.1473 | 0.4608 | 0.1803 | 0.044* | |
C18 | 0.9262 (3) | 0.4196 (2) | 0.11519 (19) | 0.0359 (6) | |
H18 | 0.9000 | 0.3341 | 0.1169 | 0.043* | |
C19 | 0.7352 (2) | 0.6281 (2) | 0.02701 (16) | 0.0255 (5) | |
C20 | 0.6387 (3) | 0.5709 (2) | −0.06908 (18) | 0.0372 (6) | |
H20 | 0.6503 | 0.5048 | −0.1000 | 0.045* | |
C21 | 0.5258 (3) | 0.6114 (3) | −0.11883 (19) | 0.0451 (7) | |
H21 | 0.4610 | 0.5743 | −0.1844 | 0.054* | |
C22 | 0.5088 (3) | 0.7067 (3) | −0.0719 (2) | 0.0423 (7) | |
H22 | 0.4329 | 0.7360 | −0.1050 | 0.051* | |
C23 | 0.6045 (2) | 0.7585 (2) | 0.02450 (19) | 0.0333 (5) | |
H23 | 0.5919 | 0.8228 | 0.0570 | 0.040* | |
C24 | 1.0708 (2) | 0.8015 (2) | 0.11849 (16) | 0.0250 (4) | |
C25 | 1.1870 (3) | 0.8527 (2) | 0.08430 (19) | 0.0367 (6) | |
H25 | 1.2285 | 0.8019 | 0.0619 | 0.044* | |
C26 | 1.2419 (3) | 0.9791 (3) | 0.0832 (2) | 0.0444 (7) | |
H26 | 1.3218 | 1.0151 | 0.0609 | 0.053* | |
C27 | 1.1782 (3) | 1.0513 (2) | 0.1153 (2) | 0.0409 (6) | |
H27 | 1.2132 | 1.1372 | 0.1143 | 0.049* | |
C28 | 1.0624 (3) | 0.9964 (2) | 0.14890 (18) | 0.0329 (5) | |
H28 | 1.0180 | 1.0456 | 0.1701 | 0.039* | |
N9 | 0.7053 (3) | 0.0811 (2) | 0.17671 (19) | 0.0425 (5) | |
O1 | 0.6818 (3) | 0.1389 (3) | 0.23751 (18) | 0.0810 (8) | |
O2 | 0.7579 (3) | 0.0012 (2) | 0.1979 (3) | 0.1035 (12) | |
O3 | 0.6834 (5) | 0.1134 (4) | 0.0945 (2) | 0.1297 (15) | |
N10 | 0.2051 (3) | 0.3037 (2) | 0.3109 (2) | 0.0463 (6) | |
O4 | 0.2775 (3) | 0.3406 (2) | 0.40190 (18) | 0.0636 (6) | |
O5 | 0.0679 (2) | 0.25210 (19) | 0.2792 (2) | 0.0688 (7) | |
O6 | 0.2740 (3) | 0.3221 (2) | 0.2514 (2) | 0.0695 (7) | |
N11 | 0.3636 (4) | −0.0592 (4) | 0.3507 (3) | 0.0822 (10) | |
C29 | 0.4999 (4) | 0.1768 (4) | 0.3903 (4) | 0.0813 (12) | |
H29A | 0.5525 | 0.2046 | 0.3445 | 0.122* | |
H29B | 0.5707 | 0.1988 | 0.4587 | 0.122* | |
H29C | 0.4278 | 0.2163 | 0.3828 | 0.122* | |
C30 | 0.4232 (4) | 0.0439 (4) | 0.3679 (3) | 0.0623 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.01659 (9) | 0.01646 (9) | 0.02448 (9) | 0.00547 (6) | 0.00380 (6) | 0.00146 (6) |
N1 | 0.0380 (11) | 0.0216 (9) | 0.0258 (10) | 0.0080 (8) | 0.0102 (8) | 0.0027 (7) |
N2 | 0.0320 (10) | 0.0327 (11) | 0.0268 (10) | 0.0149 (9) | 0.0090 (8) | 0.0052 (8) |
N3 | 0.0180 (8) | 0.0207 (9) | 0.0288 (9) | 0.0041 (7) | 0.0052 (7) | −0.0062 (7) |
N4 | 0.0180 (8) | 0.0204 (9) | 0.0275 (9) | 0.0045 (7) | 0.0087 (7) | −0.0026 (7) |
N5 | 0.0367 (11) | 0.0227 (10) | 0.0338 (11) | 0.0063 (8) | 0.0145 (9) | 0.0021 (8) |
N6 | 0.0303 (10) | 0.0342 (11) | 0.0344 (11) | 0.0151 (9) | 0.0132 (9) | 0.0068 (9) |
N7 | 0.0195 (9) | 0.0219 (9) | 0.0266 (9) | 0.0043 (7) | 0.0034 (7) | 0.0074 (7) |
N8 | 0.0222 (9) | 0.0218 (9) | 0.0230 (9) | 0.0048 (7) | 0.0041 (7) | 0.0042 (7) |
C1 | 0.0288 (11) | 0.0206 (10) | 0.0178 (10) | 0.0072 (9) | 0.0088 (8) | 0.0019 (8) |
C2 | 0.0267 (11) | 0.0248 (11) | 0.0172 (10) | 0.0080 (9) | 0.0083 (8) | 0.0019 (8) |
C3 | 0.0437 (14) | 0.0345 (13) | 0.0334 (13) | 0.0228 (11) | 0.0158 (11) | 0.0110 (10) |
C4 | 0.0504 (15) | 0.0231 (11) | 0.0302 (12) | 0.0167 (11) | 0.0144 (11) | 0.0075 (9) |
C5 | 0.0227 (10) | 0.0209 (10) | 0.0273 (11) | 0.0011 (8) | 0.0079 (9) | −0.0064 (9) |
C6 | 0.0346 (13) | 0.0308 (13) | 0.0443 (15) | 0.0004 (10) | 0.0210 (11) | −0.0030 (11) |
C7 | 0.0325 (14) | 0.0420 (16) | 0.0607 (18) | −0.0029 (12) | 0.0246 (13) | −0.0120 (14) |
C8 | 0.0197 (12) | 0.0479 (16) | 0.0647 (19) | 0.0058 (11) | 0.0126 (12) | −0.0196 (14) |
C9 | 0.0212 (11) | 0.0314 (13) | 0.0450 (14) | 0.0087 (10) | 0.0042 (10) | −0.0107 (11) |
C10 | 0.0178 (10) | 0.0246 (11) | 0.0265 (11) | 0.0056 (8) | 0.0090 (8) | −0.0013 (9) |
C11 | 0.0244 (11) | 0.0354 (13) | 0.0266 (11) | 0.0074 (10) | 0.0058 (9) | −0.0034 (10) |
C12 | 0.0239 (11) | 0.0386 (14) | 0.0344 (13) | 0.0028 (10) | 0.0050 (10) | −0.0142 (11) |
C13 | 0.0261 (12) | 0.0242 (11) | 0.0454 (14) | −0.0001 (9) | 0.0146 (11) | −0.0131 (10) |
C14 | 0.0247 (11) | 0.0201 (11) | 0.0405 (13) | 0.0044 (9) | 0.0149 (10) | −0.0029 (9) |
C15 | 0.0280 (11) | 0.0210 (10) | 0.0204 (10) | 0.0057 (9) | 0.0102 (9) | 0.0017 (8) |
C16 | 0.0268 (11) | 0.0255 (11) | 0.0194 (10) | 0.0083 (9) | 0.0103 (9) | 0.0033 (8) |
C17 | 0.0438 (14) | 0.0375 (14) | 0.0409 (14) | 0.0238 (12) | 0.0208 (12) | 0.0103 (11) |
C18 | 0.0488 (15) | 0.0243 (12) | 0.0417 (14) | 0.0159 (11) | 0.0224 (12) | 0.0051 (10) |
C19 | 0.0217 (10) | 0.0218 (10) | 0.0234 (11) | −0.0001 (8) | 0.0047 (9) | 0.0039 (8) |
C20 | 0.0319 (13) | 0.0374 (14) | 0.0262 (12) | −0.0010 (11) | 0.0048 (10) | −0.0002 (10) |
C21 | 0.0296 (13) | 0.0485 (16) | 0.0281 (13) | −0.0054 (12) | −0.0055 (10) | 0.0073 (12) |
C22 | 0.0210 (12) | 0.0460 (15) | 0.0435 (15) | 0.0036 (11) | −0.0006 (11) | 0.0237 (13) |
C23 | 0.0238 (11) | 0.0300 (12) | 0.0419 (14) | 0.0092 (10) | 0.0067 (10) | 0.0152 (10) |
C24 | 0.0236 (10) | 0.0242 (11) | 0.0206 (10) | 0.0035 (9) | 0.0052 (8) | 0.0024 (8) |
C25 | 0.0375 (13) | 0.0353 (13) | 0.0361 (13) | 0.0060 (11) | 0.0195 (11) | 0.0033 (11) |
C26 | 0.0458 (15) | 0.0380 (14) | 0.0452 (15) | −0.0009 (12) | 0.0280 (13) | 0.0082 (12) |
C27 | 0.0478 (15) | 0.0254 (12) | 0.0403 (14) | 0.0003 (11) | 0.0176 (12) | 0.0103 (11) |
C28 | 0.0362 (13) | 0.0222 (11) | 0.0325 (12) | 0.0061 (10) | 0.0074 (10) | 0.0061 (9) |
N9 | 0.0446 (13) | 0.0276 (11) | 0.0576 (15) | 0.0164 (10) | 0.0179 (11) | 0.0038 (10) |
O1 | 0.0879 (19) | 0.124 (2) | 0.0508 (14) | 0.0659 (18) | 0.0220 (13) | 0.0027 (15) |
O2 | 0.0523 (14) | 0.0291 (11) | 0.209 (4) | 0.0242 (11) | 0.0119 (18) | 0.0110 (16) |
O3 | 0.202 (4) | 0.184 (4) | 0.071 (2) | 0.125 (4) | 0.075 (2) | 0.043 (2) |
N10 | 0.0505 (15) | 0.0224 (11) | 0.0667 (17) | 0.0219 (10) | 0.0132 (13) | 0.0075 (11) |
O4 | 0.0732 (16) | 0.0563 (14) | 0.0582 (14) | 0.0345 (12) | 0.0090 (12) | −0.0004 (11) |
O5 | 0.0470 (13) | 0.0366 (11) | 0.110 (2) | 0.0152 (10) | 0.0123 (13) | 0.0097 (12) |
O6 | 0.0829 (17) | 0.0708 (16) | 0.0788 (17) | 0.0431 (14) | 0.0430 (15) | 0.0216 (13) |
N11 | 0.093 (3) | 0.092 (3) | 0.079 (2) | 0.052 (2) | 0.034 (2) | 0.008 (2) |
C29 | 0.060 (2) | 0.084 (3) | 0.115 (3) | 0.046 (2) | 0.030 (2) | 0.015 (2) |
C30 | 0.061 (2) | 0.087 (3) | 0.059 (2) | 0.052 (2) | 0.0209 (17) | 0.008 (2) |
Pd1—N7 | 2.0170 (18) | C12—H12 | 0.9400 |
Pd1—N8 | 2.0178 (18) | C13—C14 | 1.383 (3) |
Pd1—N4 | 2.0257 (17) | C13—H13 | 0.9400 |
Pd1—N3 | 2.0286 (19) | C14—H14 | 0.9400 |
N1—C4 | 1.333 (3) | C15—C16 | 1.403 (3) |
N1—C1 | 1.345 (3) | C15—C19 | 1.485 (3) |
N2—C3 | 1.329 (3) | C16—C24 | 1.493 (3) |
N2—C2 | 1.344 (3) | C17—C18 | 1.380 (4) |
N3—C9 | 1.344 (3) | C17—H17 | 0.9400 |
N3—C5 | 1.351 (3) | C18—H18 | 0.9400 |
N4—C14 | 1.347 (3) | C19—C20 | 1.388 (3) |
N4—C10 | 1.347 (3) | C20—C21 | 1.376 (4) |
N5—C18 | 1.325 (3) | C20—H20 | 0.9400 |
N5—C15 | 1.346 (3) | C21—C22 | 1.373 (4) |
N6—C17 | 1.331 (3) | C21—H21 | 0.9400 |
N6—C16 | 1.341 (3) | C22—C23 | 1.376 (4) |
N7—C19 | 1.349 (3) | C22—H22 | 0.9400 |
N7—C23 | 1.350 (3) | C23—H23 | 0.9400 |
N8—C24 | 1.349 (3) | C24—C25 | 1.381 (3) |
N8—C28 | 1.349 (3) | C25—C26 | 1.384 (4) |
C1—C2 | 1.400 (3) | C25—H25 | 0.9400 |
C1—C5 | 1.490 (3) | C26—C27 | 1.375 (4) |
C2—C10 | 1.490 (3) | C26—H26 | 0.9400 |
C3—C4 | 1.381 (4) | C27—C28 | 1.380 (4) |
C3—H3 | 0.9400 | C27—H27 | 0.9400 |
C4—H4 | 0.9400 | C28—H28 | 0.9400 |
C5—C6 | 1.385 (3) | N9—O3 | 1.211 (4) |
C6—C7 | 1.392 (4) | N9—O2 | 1.218 (3) |
C6—H6 | 0.9400 | N9—O1 | 1.219 (3) |
C7—C8 | 1.367 (4) | N10—O5 | 1.235 (3) |
C7—H7 | 0.9400 | N10—O4 | 1.245 (3) |
C8—C9 | 1.383 (4) | N10—O6 | 1.248 (3) |
C8—H8 | 0.9400 | N11—C30 | 1.123 (5) |
C9—H9 | 0.9400 | C29—C30 | 1.446 (6) |
C10—C11 | 1.384 (3) | C29—H29A | 0.9700 |
C11—C12 | 1.380 (3) | C29—H29B | 0.9700 |
C11—H11 | 0.9400 | C29—H29C | 0.9700 |
C12—C13 | 1.372 (4) | ||
N7—Pd1—N8 | 85.98 (7) | C14—C13—H13 | 120.4 |
N7—Pd1—N4 | 177.88 (7) | N4—C14—C13 | 121.8 (2) |
N8—Pd1—N4 | 92.86 (7) | N4—C14—H14 | 119.1 |
N7—Pd1—N3 | 94.14 (7) | C13—C14—H14 | 119.1 |
N8—Pd1—N3 | 178.89 (7) | N5—C15—C16 | 120.7 (2) |
N4—Pd1—N3 | 86.99 (7) | N5—C15—C19 | 113.75 (19) |
C4—N1—C1 | 116.7 (2) | C16—C15—C19 | 125.20 (19) |
C3—N2—C2 | 116.9 (2) | N6—C16—C15 | 120.9 (2) |
C9—N3—C5 | 119.0 (2) | N6—C16—C24 | 113.55 (19) |
C9—N3—Pd1 | 121.60 (17) | C15—C16—C24 | 125.26 (19) |
C5—N3—Pd1 | 119.40 (14) | N6—C17—C18 | 121.9 (2) |
C14—N4—C10 | 119.34 (19) | N6—C17—H17 | 119.0 |
C14—N4—Pd1 | 119.98 (15) | C18—C17—H17 | 119.0 |
C10—N4—Pd1 | 120.63 (14) | N5—C18—C17 | 121.6 (2) |
C18—N5—C15 | 117.5 (2) | N5—C18—H18 | 119.2 |
C17—N6—C16 | 117.2 (2) | C17—C18—H18 | 119.2 |
C19—N7—C23 | 119.2 (2) | N7—C19—C20 | 120.7 (2) |
C19—N7—Pd1 | 120.11 (14) | N7—C19—C15 | 119.79 (18) |
C23—N7—Pd1 | 120.68 (17) | C20—C19—C15 | 119.5 (2) |
C24—N8—C28 | 119.8 (2) | C21—C20—C19 | 119.6 (3) |
C24—N8—Pd1 | 120.24 (14) | C21—C20—H20 | 120.2 |
C28—N8—Pd1 | 119.90 (16) | C19—C20—H20 | 120.2 |
N1—C1—C2 | 121.4 (2) | C22—C21—C20 | 119.5 (2) |
N1—C1—C5 | 113.28 (19) | C22—C21—H21 | 120.3 |
C2—C1—C5 | 125.07 (19) | C20—C21—H21 | 120.3 |
N2—C2—C1 | 120.8 (2) | C21—C22—C23 | 119.0 (2) |
N2—C2—C10 | 113.82 (18) | C21—C22—H22 | 120.5 |
C1—C2—C10 | 125.21 (19) | C23—C22—H22 | 120.5 |
N2—C3—C4 | 122.2 (2) | N7—C23—C22 | 122.0 (2) |
N2—C3—H3 | 118.9 | N7—C23—H23 | 119.0 |
C4—C3—H3 | 118.9 | C22—C23—H23 | 119.0 |
N1—C4—C3 | 121.7 (2) | N8—C24—C25 | 120.7 (2) |
N1—C4—H4 | 119.2 | N8—C24—C16 | 119.67 (19) |
C3—C4—H4 | 119.2 | C25—C24—C16 | 119.6 (2) |
N3—C5—C6 | 121.3 (2) | C24—C25—C26 | 119.7 (2) |
N3—C5—C1 | 119.16 (19) | C24—C25—H25 | 120.2 |
C6—C5—C1 | 119.5 (2) | C26—C25—H25 | 120.2 |
C5—C6—C7 | 119.1 (3) | C27—C26—C25 | 119.1 (2) |
C5—C6—H6 | 120.4 | C27—C26—H26 | 120.4 |
C7—C6—H6 | 120.4 | C25—C26—H26 | 120.4 |
C8—C7—C6 | 119.2 (3) | C26—C27—C28 | 119.3 (2) |
C8—C7—H7 | 120.4 | C26—C27—H27 | 120.3 |
C6—C7—H7 | 120.4 | C28—C27—H27 | 120.3 |
C7—C8—C9 | 119.3 (3) | N8—C28—C27 | 121.3 (2) |
C7—C8—H8 | 120.4 | N8—C28—H28 | 119.3 |
C9—C8—H8 | 120.4 | C27—C28—H28 | 119.3 |
N3—C9—C8 | 122.1 (3) | O3—N9—O2 | 120.7 (3) |
N3—C9—H9 | 119.0 | O3—N9—O1 | 116.2 (3) |
C8—C9—H9 | 119.0 | O2—N9—O1 | 122.9 (3) |
N4—C10—C11 | 120.8 (2) | O5—N10—O4 | 121.2 (3) |
N4—C10—C2 | 119.52 (18) | O5—N10—O6 | 120.2 (3) |
C11—C10—C2 | 119.6 (2) | O4—N10—O6 | 118.6 (3) |
C12—C11—C10 | 119.8 (2) | C30—C29—H29A | 109.5 |
C12—C11—H11 | 120.1 | C30—C29—H29B | 109.5 |
C10—C11—H11 | 120.1 | H29A—C29—H29B | 109.5 |
C13—C12—C11 | 119.1 (2) | C30—C29—H29C | 109.5 |
C13—C12—H12 | 120.4 | H29A—C29—H29C | 109.5 |
C11—C12—H12 | 120.4 | H29B—C29—H29C | 109.5 |
C12—C13—C14 | 119.1 (2) | N11—C30—C29 | 179.9 (5) |
C12—C13—H13 | 120.4 | ||
C4—N1—C1—C2 | −0.6 (3) | C18—N5—C15—C16 | 2.3 (3) |
C4—N1—C1—C5 | −175.51 (19) | C18—N5—C15—C19 | 176.1 (2) |
C3—N2—C2—C1 | 3.9 (3) | C17—N6—C16—C15 | −3.0 (3) |
C3—N2—C2—C10 | 179.72 (19) | C17—N6—C16—C24 | −177.0 (2) |
N1—C1—C2—N2 | −3.6 (3) | N5—C15—C16—N6 | 0.8 (3) |
C5—C1—C2—N2 | 170.7 (2) | C19—C15—C16—N6 | −172.3 (2) |
N1—C1—C2—C10 | −178.84 (19) | N5—C15—C16—C24 | 174.0 (2) |
C5—C1—C2—C10 | −4.5 (3) | C19—C15—C16—C24 | 1.0 (3) |
C2—N2—C3—C4 | −0.4 (3) | C16—N6—C17—C18 | 2.1 (4) |
C1—N1—C4—C3 | 4.1 (3) | C15—N5—C18—C17 | −3.2 (4) |
N2—C3—C4—N1 | −3.8 (4) | N6—C17—C18—N5 | 1.0 (4) |
C9—N3—C5—C6 | 2.2 (3) | C23—N7—C19—C20 | −2.4 (3) |
Pd1—N3—C5—C6 | −177.06 (17) | Pd1—N7—C19—C20 | 179.11 (16) |
C9—N3—C5—C1 | 179.91 (19) | C23—N7—C19—C15 | 177.89 (19) |
Pd1—N3—C5—C1 | 0.7 (3) | Pd1—N7—C19—C15 | −0.6 (3) |
N1—C1—C5—N3 | −127.1 (2) | N5—C15—C19—N7 | 131.2 (2) |
C2—C1—C5—N3 | 58.2 (3) | C16—C15—C19—N7 | −55.3 (3) |
N1—C1—C5—C6 | 50.6 (3) | N5—C15—C19—C20 | −48.5 (3) |
C2—C1—C5—C6 | −124.1 (2) | C16—C15—C19—C20 | 125.0 (2) |
N3—C5—C6—C7 | −2.3 (3) | N7—C19—C20—C21 | 2.7 (3) |
C1—C5—C6—C7 | 179.9 (2) | C15—C19—C20—C21 | −177.6 (2) |
C5—C6—C7—C8 | 0.5 (4) | C19—C20—C21—C22 | −1.1 (4) |
C6—C7—C8—C9 | 1.3 (4) | C20—C21—C22—C23 | −0.6 (4) |
C5—N3—C9—C8 | −0.2 (3) | C19—N7—C23—C22 | 0.6 (3) |
Pd1—N3—C9—C8 | 179.01 (18) | Pd1—N7—C23—C22 | 179.05 (17) |
C7—C8—C9—N3 | −1.6 (4) | C21—C22—C23—N7 | 0.9 (4) |
C14—N4—C10—C11 | 0.1 (3) | C28—N8—C24—C25 | 2.4 (3) |
Pd1—N4—C10—C11 | 177.58 (16) | Pd1—N8—C24—C25 | −174.04 (17) |
C14—N4—C10—C2 | −177.47 (19) | C28—N8—C24—C16 | −178.37 (19) |
Pd1—N4—C10—C2 | 0.0 (3) | Pd1—N8—C24—C16 | 5.2 (3) |
N2—C2—C10—N4 | 131.5 (2) | N6—C16—C24—N8 | −134.9 (2) |
C1—C2—C10—N4 | −52.9 (3) | C15—C16—C24—N8 | 51.4 (3) |
N2—C2—C10—C11 | −46.0 (3) | N6—C16—C24—C25 | 44.3 (3) |
C1—C2—C10—C11 | 129.5 (2) | C15—C16—C24—C25 | −129.4 (2) |
N4—C10—C11—C12 | −1.5 (3) | N8—C24—C25—C26 | −0.9 (4) |
C2—C10—C11—C12 | 176.1 (2) | C16—C24—C25—C26 | 179.9 (2) |
C10—C11—C12—C13 | 1.1 (4) | C24—C25—C26—C27 | −0.8 (4) |
C11—C12—C13—C14 | 0.5 (4) | C25—C26—C27—C28 | 0.8 (4) |
C10—N4—C14—C13 | 1.7 (3) | C24—N8—C28—C27 | −2.4 (3) |
Pd1—N4—C14—C13 | −175.86 (17) | Pd1—N8—C28—C27 | 174.09 (18) |
C12—C13—C14—N4 | −2.0 (3) | C26—C27—C28—N8 | 0.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O4i | 0.94 | 2.43 | 3.344 (3) | 164 |
C4—H4···O1 | 0.94 | 2.51 | 3.330 (4) | 146 |
C9—H9···O2ii | 0.94 | 2.40 | 3.113 (4) | 133 |
C14—H14···O5iii | 0.94 | 2.43 | 3.257 (3) | 147 |
C17—H17···O6i | 0.94 | 2.43 | 3.343 (3) | 164 |
C22—H22···O3iv | 0.94 | 2.45 | 3.273 (5) | 146 |
C23—H23···O2ii | 0.94 | 2.54 | 3.275 (4) | 136 |
C29—H29A···O1 | 0.97 | 2.58 | 3.405 (5) | 144 |
C29—H29C···O4 | 0.97 | 2.51 | 3.459 (4) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) −x+1, −y+1, −z. |
Acknowledgements
The author thanks the KBSI, Seoul Center, for the X-ray data collection.
Funding information
This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (grant No. 2018R1D1A1B07050550).
References
Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ha, K. (2011a). Acta Cryst. E67, m1615. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ha, K. (2011b). Acta Cryst. E67, m1634. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ha, K. (2011c). Acta Cryst. E67, m1896. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ha, K. (2011d). Acta Cryst. E67, m1626. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ha, K. (2012). Acta Cryst. E68, m144. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Yam, V. W.-W., Lee, V. W.-M. & Cheung, K.-K. (1994). J. Chem. Soc. Chem. Commun. pp. 2075–2076. CrossRef Web of Science Google Scholar
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