metal-organic compounds
{4,4′-Dibromo-2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenolato-κ4O,N,N′,O′}nickel(II)
aChonnam National University, School of Chemical Engineering, Research Institute of Catalysis, Gwangju, Republic of Korea
*Correspondence e-mail: hakwang@chonnam.ac.kr
In the title compound, [Ni(C20H18Br2N2O2)], the NiII ion is four-coordinated in a slightly distorted square-planar coordination geometry defined by two N atoms and two O atoms of the tetradentate dianionic 4,4′-dibromo-2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenolato ligand. Pairs of complex molecules are assembled by intermolecular C—H⋯O hydrogen bonds with d(C⋯O) = 3.247 (4) Å.
CCDC reference: 2058387
Structure description
With reference to the title compound, [Ni(saldach)] (saldach = 4,4′-dibromo- 2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenolato), the crystal structures of the tetradentate Schiff base (H2-saldach) ligand (Yi & Hu, 2009; Ha, 2012), and related saldach–metal complexes [Cu(saldach)] (Tohidiyan et al., 2017) and [Zn(saldach)(pyridine)] (Szłyk et al., 2005) have been determined previously.
In the title complex, the central NiII cation is four-coordinated in a slightly distorted square-planar coordination geometry defined by the N1, N2, O1 and O2 atoms of the tetradentate dianionic saldach ligand (Fig. 1). The tight N—Ni—N and N—Ni—O chelating angles of <N1—Ni1—N2 = 86.13 (10)°, <N1—Ni1—O1 = 94.64 (10)° and <N2—Ni1—O2 = 95.02 (10)° form the square-plane. The Ni—N and Ni—O bonds are almost equal [1.844 (2)–1.858 (2) Å] and the nearly planar benzene rings of the saldach ligand are slightly twisted with a dihedral angle of 2.9 (2)° between them. The dihedral angles between the least-squares plane [maximum deviation = 0.066 (1) Å] of the Ni square-plane (Ni1/O1/O2/N1/N2) and the benzene rings are 7.2 (2) and 4.4 (2)°, respectively. In the (Fig. 2), pairs of complex molecules are assembled by intermolecular C—H⋯O hydrogen bonds (Table 1). In addition, the complex displays several intermolecular π–π interactions between adjacent benzene rings. For Cg1 (the centroid of ring C8–C13) and Cg2i [the centroid of ring C15—C20; symmetry code: (i) −x + 1, −y + 1, −z + 1], the centroid–centroid distance is 4.081 (2) Å and the dihedral angle between the ring planes is 2.9 (1)°.
Synthesis and crystallization
To a solution of Ni(acac)2 (acac = pentane-2,4-dionate; 0.1231 g, 0.479 mmol) in acetone (30 ml) was added 4,4′-dibromo-2,2′-[cyclohexane-1,2-diylbis(nitrilomethanylylidene)]diphenol (0.2320 g, 0.483 mmol; Ha, 2012) and stirred for 1 h at room temperature. After addition of ether (30 ml), the formed precipitate was separated by filtration, washed with ether, and dried at 323 K, to give a brown powder (0.2464 g). Brown crystals suitable for X-ray analysis were obtained by slow evaporation from a dimethyl sulfoxide (DMSO) solution at 363 K.
Refinement
Crystal data, data collection and structure . The highest peak (0.77 e Å−3) and the deepest hole (−0.51 e Å−3) in the difference Fourier map are located 0.86 and 0.70 Å, respectively, from the atoms Br1 and Br2.
details are summarized in Table 2Structural data
CCDC reference: 2058387
https://doi.org/10.1107/S2414314621000845/sj4220sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000845/sj4220Isup2.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); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015b).[Ni(C20H18Br2N2O2)] | F(000) = 1064 |
Mr = 536.89 | Dx = 1.904 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.5179 (4) Å | Cell parameters from 9977 reflections |
b = 13.6343 (5) Å | θ = 2.5–26.0° |
c = 10.4966 (4) Å | µ = 5.32 mm−1 |
β = 104.510 (1)° | T = 223 K |
V = 1872.89 (11) Å3 | Block, brown |
Z = 4 | 0.14 × 0.10 × 0.07 mm |
PHOTON 100 CMOS detector diffractometer | 3107 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.059 |
φ and ω scans | θmax = 26.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −16→16 |
Tmin = 0.618, Tmax = 0.745 | k = −16→16 |
50588 measured reflections | l = −12→12 |
3710 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0258P)2 + 2.4859P] where P = (Fo2 + 2Fc2)/3 |
3710 reflections | (Δ/σ)max = 0.002 |
244 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
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. Hydrogen atoms on C atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.94, 0.98 or 0.99 Å and Uiso(H) = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | ||
Br1 | 1.00079 (3) | 0.44652 (3) | 0.23580 (4) | 0.05730 (14) | |
Br2 | 0.08652 (3) | 0.78593 (3) | 0.58203 (4) | 0.05165 (13) | |
Ni1 | 0.49753 (3) | 0.55203 (3) | 0.34846 (4) | 0.02442 (10) | |
O1 | 0.62893 (15) | 0.60079 (16) | 0.3841 (2) | 0.0304 (5) | |
O2 | 0.47131 (15) | 0.66161 (16) | 0.4383 (2) | 0.0301 (5) | |
N1 | 0.52417 (17) | 0.44688 (18) | 0.2516 (2) | 0.0252 (5) | |
N2 | 0.36814 (17) | 0.49806 (19) | 0.3268 (2) | 0.0267 (5) | |
C1 | 0.4343 (2) | 0.3849 (2) | 0.1927 (3) | 0.0269 (6) | |
H1 | 0.4565 | 0.3161 | 0.1883 | 0.032* | |
C2 | 0.3649 (2) | 0.3921 (2) | 0.2871 (3) | 0.0284 (7) | |
H2 | 0.3975 | 0.3537 | 0.3667 | 0.034* | |
C3 | 0.2600 (2) | 0.3463 (3) | 0.2275 (3) | 0.0339 (7) | |
H3A | 0.2675 | 0.2748 | 0.2255 | 0.041* | |
H3B | 0.2146 | 0.3613 | 0.2844 | 0.041* | |
C4 | 0.2111 (2) | 0.3822 (3) | 0.0896 (3) | 0.0374 (8) | |
H4A | 0.1956 | 0.4523 | 0.0921 | 0.045* | |
H4B | 0.1468 | 0.3471 | 0.0545 | 0.045* | |
C5 | 0.2827 (2) | 0.3653 (3) | 0.0006 (3) | 0.0361 (8) | |
H5A | 0.2505 | 0.3886 | −0.0884 | 0.043* | |
H5B | 0.2966 | 0.2950 | −0.0041 | 0.043* | |
C6 | 0.3832 (2) | 0.4208 (2) | 0.0554 (3) | 0.0308 (7) | |
H6A | 0.4290 | 0.4105 | −0.0025 | 0.037* | |
H6B | 0.3693 | 0.4912 | 0.0579 | 0.037* | |
C7 | 0.6106 (2) | 0.4235 (2) | 0.2282 (3) | 0.0265 (6) | |
H7 | 0.6122 | 0.3676 | 0.1762 | 0.032* | |
C8 | 0.7038 (2) | 0.4763 (2) | 0.2755 (3) | 0.0255 (6) | |
C9 | 0.7083 (2) | 0.5611 (2) | 0.3546 (3) | 0.0271 (7) | |
C10 | 0.8051 (2) | 0.6037 (2) | 0.4047 (3) | 0.0325 (7) | |
H10 | 0.8112 | 0.6575 | 0.4622 | 0.039* | |
C11 | 0.8910 (2) | 0.5690 (3) | 0.3719 (3) | 0.0370 (8) | |
H11 | 0.9545 | 0.5994 | 0.4058 | 0.044* | |
C12 | 0.8835 (2) | 0.4889 (3) | 0.2886 (3) | 0.0336 (7) | |
C13 | 0.7927 (2) | 0.4414 (2) | 0.2423 (3) | 0.0304 (7) | |
H13 | 0.7892 | 0.3857 | 0.1887 | 0.036* | |
C14 | 0.2916 (2) | 0.5380 (2) | 0.3591 (3) | 0.0290 (7) | |
H14 | 0.2294 | 0.5035 | 0.3390 | 0.035* | |
C15 | 0.2940 (2) | 0.6313 (2) | 0.4236 (3) | 0.0268 (6) | |
C16 | 0.3855 (2) | 0.6850 (2) | 0.4669 (3) | 0.0255 (6) | |
C17 | 0.3841 (2) | 0.7673 (2) | 0.5479 (3) | 0.0310 (7) | |
H17 | 0.4446 | 0.8031 | 0.5803 | 0.037* | |
C18 | 0.2964 (3) | 0.7962 (2) | 0.5805 (3) | 0.0347 (7) | |
H18 | 0.2974 | 0.8511 | 0.6350 | 0.042* | |
C19 | 0.2063 (2) | 0.7446 (2) | 0.5329 (3) | 0.0332 (7) | |
C20 | 0.2041 (2) | 0.6637 (2) | 0.4562 (3) | 0.0316 (7) | |
H20 | 0.1426 | 0.6293 | 0.4248 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02496 (17) | 0.0832 (3) | 0.0682 (3) | 0.00022 (18) | 0.02006 (17) | −0.0224 (2) |
Br2 | 0.0399 (2) | 0.0644 (3) | 0.0559 (2) | 0.01865 (18) | 0.02165 (17) | −0.0045 (2) |
Ni1 | 0.01809 (18) | 0.0301 (2) | 0.0257 (2) | −0.00166 (15) | 0.00659 (15) | −0.00440 (17) |
O1 | 0.0212 (10) | 0.0346 (12) | 0.0371 (13) | −0.0038 (9) | 0.0107 (9) | −0.0096 (10) |
O2 | 0.0239 (10) | 0.0335 (12) | 0.0350 (12) | −0.0034 (9) | 0.0112 (9) | −0.0075 (10) |
N1 | 0.0207 (12) | 0.0302 (13) | 0.0250 (13) | −0.0024 (10) | 0.0061 (10) | −0.0024 (11) |
N2 | 0.0220 (12) | 0.0334 (15) | 0.0245 (13) | −0.0024 (11) | 0.0055 (10) | −0.0044 (11) |
C1 | 0.0238 (14) | 0.0274 (16) | 0.0292 (16) | −0.0021 (12) | 0.0062 (12) | −0.0055 (13) |
C2 | 0.0260 (15) | 0.0305 (17) | 0.0283 (17) | −0.0044 (13) | 0.0059 (12) | −0.0003 (13) |
C3 | 0.0322 (17) | 0.0345 (18) | 0.0372 (19) | −0.0062 (14) | 0.0129 (14) | −0.0041 (15) |
C4 | 0.0233 (15) | 0.041 (2) | 0.044 (2) | −0.0023 (14) | 0.0019 (14) | −0.0008 (16) |
C5 | 0.0352 (17) | 0.043 (2) | 0.0266 (17) | −0.0046 (15) | 0.0018 (14) | 0.0005 (15) |
C6 | 0.0305 (16) | 0.0333 (18) | 0.0289 (17) | −0.0022 (13) | 0.0077 (13) | −0.0010 (14) |
C7 | 0.0265 (15) | 0.0311 (17) | 0.0220 (15) | 0.0022 (12) | 0.0067 (12) | −0.0017 (12) |
C8 | 0.0216 (14) | 0.0326 (17) | 0.0226 (15) | 0.0024 (12) | 0.0061 (12) | 0.0028 (13) |
C9 | 0.0217 (14) | 0.0340 (17) | 0.0269 (16) | 0.0018 (13) | 0.0084 (12) | 0.0019 (13) |
C10 | 0.0256 (15) | 0.0359 (18) | 0.0350 (18) | −0.0018 (13) | 0.0059 (13) | −0.0063 (15) |
C11 | 0.0211 (15) | 0.048 (2) | 0.041 (2) | −0.0033 (14) | 0.0053 (14) | −0.0051 (16) |
C12 | 0.0202 (14) | 0.046 (2) | 0.0361 (19) | 0.0059 (14) | 0.0092 (13) | 0.0017 (15) |
C13 | 0.0273 (15) | 0.0382 (18) | 0.0263 (16) | 0.0037 (14) | 0.0077 (13) | −0.0019 (14) |
C14 | 0.0202 (14) | 0.0404 (19) | 0.0269 (16) | −0.0041 (13) | 0.0066 (12) | −0.0025 (14) |
C15 | 0.0262 (15) | 0.0322 (17) | 0.0227 (15) | 0.0013 (13) | 0.0073 (12) | 0.0025 (13) |
C16 | 0.0257 (14) | 0.0286 (16) | 0.0237 (15) | 0.0012 (12) | 0.0092 (12) | 0.0038 (13) |
C17 | 0.0321 (16) | 0.0277 (17) | 0.0349 (18) | 0.0002 (13) | 0.0117 (14) | 0.0003 (14) |
C18 | 0.0433 (19) | 0.0314 (18) | 0.0342 (18) | 0.0060 (15) | 0.0186 (15) | 0.0016 (14) |
C19 | 0.0322 (16) | 0.0380 (19) | 0.0322 (18) | 0.0116 (14) | 0.0136 (14) | 0.0070 (15) |
C20 | 0.0251 (15) | 0.0403 (19) | 0.0299 (17) | 0.0033 (14) | 0.0081 (13) | 0.0011 (14) |
Br1—C12 | 1.896 (3) | C5—H5B | 0.9800 |
Br2—C19 | 1.903 (3) | C6—H6A | 0.9800 |
Ni1—N1 | 1.844 (2) | C6—H6B | 0.9800 |
Ni1—O1 | 1.8449 (19) | C7—C8 | 1.429 (4) |
Ni1—O2 | 1.848 (2) | C7—H7 | 0.9400 |
Ni1—N2 | 1.858 (2) | C8—C13 | 1.414 (4) |
O1—C9 | 1.307 (3) | C8—C9 | 1.415 (4) |
O2—C16 | 1.309 (3) | C9—C10 | 1.407 (4) |
N1—C7 | 1.293 (4) | C10—C11 | 1.375 (4) |
N1—C1 | 1.482 (4) | C10—H10 | 0.9400 |
N2—C14 | 1.288 (4) | C11—C12 | 1.386 (5) |
N2—C2 | 1.501 (4) | C11—H11 | 0.9400 |
C1—C6 | 1.515 (4) | C12—C13 | 1.365 (4) |
C1—C2 | 1.528 (4) | C13—H13 | 0.9400 |
C1—H1 | 0.9900 | C14—C15 | 1.437 (4) |
C2—C3 | 1.532 (4) | C14—H14 | 0.9400 |
C2—H2 | 0.9900 | C15—C16 | 1.411 (4) |
C3—C4 | 1.514 (5) | C15—C20 | 1.413 (4) |
C3—H3A | 0.9800 | C16—C17 | 1.412 (4) |
C3—H3B | 0.9800 | C17—C18 | 1.371 (4) |
C4—C5 | 1.522 (5) | C17—H17 | 0.9400 |
C4—H4A | 0.9800 | C18—C19 | 1.386 (5) |
C4—H4B | 0.9800 | C18—H18 | 0.9400 |
C5—C6 | 1.534 (4) | C19—C20 | 1.361 (5) |
C5—H5A | 0.9800 | C20—H20 | 0.9400 |
N1—Ni1—O1 | 94.64 (10) | C5—C6—H6A | 109.6 |
N1—Ni1—O2 | 177.02 (10) | C1—C6—H6B | 109.6 |
O1—Ni1—O2 | 84.45 (9) | C5—C6—H6B | 109.6 |
N1—Ni1—N2 | 86.13 (10) | H6A—C6—H6B | 108.1 |
O1—Ni1—N2 | 175.08 (11) | N1—C7—C8 | 124.7 (3) |
O2—Ni1—N2 | 95.02 (10) | N1—C7—H7 | 117.6 |
C9—O1—Ni1 | 127.51 (19) | C8—C7—H7 | 117.6 |
C16—O2—Ni1 | 127.46 (19) | C13—C8—C9 | 120.3 (3) |
C7—N1—C1 | 117.7 (2) | C13—C8—C7 | 118.3 (3) |
C7—N1—Ni1 | 127.4 (2) | C9—C8—C7 | 121.4 (3) |
C1—N1—Ni1 | 114.85 (18) | O1—C9—C10 | 118.8 (3) |
C14—N2—C2 | 120.7 (3) | O1—C9—C8 | 124.1 (3) |
C14—N2—Ni1 | 126.5 (2) | C10—C9—C8 | 117.1 (3) |
C2—N2—Ni1 | 112.07 (18) | C11—C10—C9 | 121.9 (3) |
N1—C1—C6 | 110.1 (2) | C11—C10—H10 | 119.1 |
N1—C1—C2 | 105.4 (2) | C9—C10—H10 | 119.1 |
C6—C1—C2 | 112.9 (2) | C10—C11—C12 | 119.7 (3) |
N1—C1—H1 | 109.5 | C10—C11—H11 | 120.1 |
C6—C1—H1 | 109.5 | C12—C11—H11 | 120.1 |
C2—C1—H1 | 109.5 | C13—C12—C11 | 121.0 (3) |
N2—C2—C1 | 105.2 (2) | C13—C12—Br1 | 119.7 (3) |
N2—C2—C3 | 117.7 (3) | C11—C12—Br1 | 119.3 (2) |
C1—C2—C3 | 111.4 (2) | C12—C13—C8 | 119.7 (3) |
N2—C2—H2 | 107.4 | C12—C13—H13 | 120.1 |
C1—C2—H2 | 107.4 | C8—C13—H13 | 120.1 |
C3—C2—H2 | 107.4 | N2—C14—C15 | 125.0 (3) |
C4—C3—C2 | 113.4 (3) | N2—C14—H14 | 117.5 |
C4—C3—H3A | 108.9 | C15—C14—H14 | 117.5 |
C2—C3—H3A | 108.9 | C16—C15—C20 | 119.8 (3) |
C4—C3—H3B | 108.9 | C16—C15—C14 | 121.7 (3) |
C2—C3—H3B | 108.9 | C20—C15—C14 | 118.2 (3) |
H3A—C3—H3B | 107.7 | O2—C16—C15 | 123.8 (3) |
C3—C4—C5 | 110.2 (3) | O2—C16—C17 | 118.6 (3) |
C3—C4—H4A | 109.6 | C15—C16—C17 | 117.6 (3) |
C5—C4—H4A | 109.6 | C18—C17—C16 | 121.4 (3) |
C3—C4—H4B | 109.6 | C18—C17—H17 | 119.3 |
C5—C4—H4B | 109.6 | C16—C17—H17 | 119.3 |
H4A—C4—H4B | 108.1 | C17—C18—C19 | 120.1 (3) |
C4—C5—C6 | 109.6 (3) | C17—C18—H18 | 120.0 |
C4—C5—H5A | 109.8 | C19—C18—H18 | 120.0 |
C6—C5—H5A | 109.8 | C20—C19—C18 | 120.7 (3) |
C4—C5—H5B | 109.8 | C20—C19—Br2 | 120.4 (3) |
C6—C5—H5B | 109.8 | C18—C19—Br2 | 118.9 (2) |
H5A—C5—H5B | 108.2 | C19—C20—C15 | 120.3 (3) |
C1—C6—C5 | 110.3 (3) | C19—C20—H20 | 119.9 |
C1—C6—H6A | 109.6 | C15—C20—H20 | 119.9 |
N1—Ni1—O1—C9 | −5.3 (3) | Ni1—O1—C9—C10 | −172.2 (2) |
O2—Ni1—O1—C9 | 177.5 (3) | Ni1—O1—C9—C8 | 7.2 (4) |
O1—Ni1—O2—C16 | −176.7 (3) | C13—C8—C9—O1 | 176.5 (3) |
N2—Ni1—O2—C16 | −1.6 (3) | C7—C8—C9—O1 | −4.1 (5) |
O1—Ni1—N1—C7 | 1.5 (3) | C13—C8—C9—C10 | −4.1 (4) |
N2—Ni1—N1—C7 | −173.6 (3) | C7—C8—C9—C10 | 175.3 (3) |
O1—Ni1—N1—C1 | −176.9 (2) | O1—C9—C10—C11 | −176.4 (3) |
N2—Ni1—N1—C1 | 8.0 (2) | C8—C9—C10—C11 | 4.1 (5) |
N1—Ni1—N2—C14 | −172.0 (3) | C9—C10—C11—C12 | −0.8 (5) |
O2—Ni1—N2—C14 | 5.3 (3) | C10—C11—C12—C13 | −2.6 (5) |
N1—Ni1—N2—C2 | 17.9 (2) | C10—C11—C12—Br1 | 176.3 (3) |
O2—Ni1—N2—C2 | −164.82 (19) | C11—C12—C13—C8 | 2.5 (5) |
C7—N1—C1—C6 | −87.0 (3) | Br1—C12—C13—C8 | −176.4 (2) |
Ni1—N1—C1—C6 | 91.6 (2) | C9—C8—C13—C12 | 1.0 (5) |
C7—N1—C1—C2 | 151.0 (3) | C7—C8—C13—C12 | −178.5 (3) |
Ni1—N1—C1—C2 | −30.4 (3) | C2—N2—C14—C15 | 166.6 (3) |
C14—N2—C2—C1 | 151.3 (3) | Ni1—N2—C14—C15 | −2.7 (5) |
Ni1—N2—C2—C1 | −38.0 (3) | N2—C14—C15—C16 | −4.9 (5) |
C14—N2—C2—C3 | 26.6 (4) | N2—C14—C15—C20 | −178.1 (3) |
Ni1—N2—C2—C3 | −162.6 (2) | Ni1—O2—C16—C15 | −4.8 (4) |
N1—C1—C2—N2 | 41.5 (3) | Ni1—O2—C16—C17 | 173.8 (2) |
C6—C1—C2—N2 | −78.7 (3) | C20—C15—C16—O2 | −178.2 (3) |
N1—C1—C2—C3 | 170.1 (2) | C14—C15—C16—O2 | 8.8 (5) |
C6—C1—C2—C3 | 49.8 (4) | C20—C15—C16—C17 | 3.2 (4) |
N2—C2—C3—C4 | 71.7 (4) | C14—C15—C16—C17 | −169.8 (3) |
C1—C2—C3—C4 | −49.8 (4) | O2—C16—C17—C18 | 179.4 (3) |
C2—C3—C4—C5 | 55.3 (4) | C15—C16—C17—C18 | −2.0 (5) |
C3—C4—C5—C6 | −59.6 (4) | C16—C17—C18—C19 | −0.4 (5) |
N1—C1—C6—C5 | −172.9 (2) | C17—C18—C19—C20 | 1.5 (5) |
C2—C1—C6—C5 | −55.5 (3) | C17—C18—C19—Br2 | 179.2 (2) |
C4—C5—C6—C1 | 59.9 (3) | C18—C19—C20—C15 | −0.2 (5) |
C1—N1—C7—C8 | 178.9 (3) | Br2—C19—C20—C15 | −177.8 (2) |
Ni1—N1—C7—C8 | 0.5 (5) | C16—C15—C20—C19 | −2.3 (5) |
N1—C7—C8—C13 | 179.6 (3) | C14—C15—C20—C19 | 171.0 (3) |
N1—C7—C8—C9 | 0.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.99 | 2.36 | 3.247 (4) | 149 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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).
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