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metal-organic compounds
H-pyrazol-1-yl)methyl]pyridine}cobalt(II)
of dichlorido{2,6-bis[(3-phenyl-1aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
*Correspondence e-mail: skkang@cnu.ac.kr
In the title complex, [CoCl2(C25H21N5)], the CoII atom is coordinated by two Cl atoms and two N atoms, provided by a tridentate pyrazolylpyridyl ligand, forming a slightly distorted tetrahedral geometry [range of angles: 96.51 (10) (chelate ring) to 118.60 (9)°]. The dihedral angle between Cl/Co/Cl and N/Co/N planes is 86.83 (7)°. The chelate ring has the conformation of a distorted boat. The dihedral angle between pyridyl ring and the coordinated pyrazolyl ring is 56.16 (12)°. The uncoordinated pyrazolyl ring is almost perpendicular to the pyridyl ring with the dihedral angle of 87.49 (10)°. In the crystal packing, intermolecular phenyl-C—H ⋯π(pyridyl) interactions generate dimeric aggregates. These are connected into a zigzag supramolecular chain along the c-axis direction via π–π interactions [inter-centroid distance between pyridyl and phenyl rings = 3.664 (2) Å].
Keywords: crystal structure; CoII complex; pyrazolylpyridyl; C—H ⋯π interactions; π–π interactions.
CCDC reference: 1051138
1. Related literature
For the synthesis of the title compound, see: Reger et al. (2005); Son et al. (2014
). For metal complexes with similar ligands, see: Massoud et al. (2013
); Sharma et al. (2011
); Ojwach et al. (2007
); Manikandan et al. (2000
, 2001
); Halcrow & Kilner (2002
); Foster et al. (2002
). For the potential applications of the ligand in catalysis, see: Karam et al. (2005
).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
|
|
Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002
); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015
); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012
); software used to prepare material for publication: WinGX (Farrugia, 2012
).
Supporting information
CCDC reference: 1051138
10.1107/S2056989015003862/tk5360sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015003862/tk5360Isup2.hkl
To a stirred solution of 2,6-pyridinedimethanol (0.28 g, 2.0 mmol) and NaOH (0.8 g, 20 mmol) in tetrahydrofuran (THF)/water (7.5/7.5 ml) was added a solution of p-toluenesulfonyl chloride (0.76 g, 4.0 mmol) in THF (7.5 ml) at 0 °C. After 4 h of stirring, the mixture was poured into 20 ml of water and extracted with methylene chloride three times. The organic layer was washed with saturated aqueous NaCl solution and distilled water, and dried over Na2SO4; the solvent was removed in vacuo to afford 2,6-pyridine-dimethylene-ditosylate (0.788 g, 88%) as a white powder. In a separate flask under a nitrogen atmosphere, a solution of 3-phenyl-1H-pyrazole (0.61 g, 5.34 mmol) in dry THF (10 ml) was added drop-wise to a suspension of NaH (0.13 g, 5.34 mmol) in dry THF (10 ml) at 0 °C. After 15 min of stirring, a solution of 2,6-pyridine-dimethylene-ditosylate (1.20 g, 2.67 mmol) in dry THF (15 ml) was added to this solution; the mixture was stirred overnight, filtered, and the solvent was removed. The crude product was purified by
on silica gel with ethyl acetate : hexane = 1:1 as to afford 0.41 g (40%) of pure ligand as a white oil.To a solution of CoCl2 (2.6 mg, 0.02 mmol) in THF (2 ml) was added a solution of the organic ligand (7.8 mg, 0.02 mmol) in THF (2 ml) drop-wise at 40 °C. The solution was stirred vigorously. A deep-blue suspension was formed immediately. The product was isolated as a blue powder by removing the solvent, washed repeatedly with THF followed by diethyl ether, and dried in vacuo. Deep-blue single crystals of the title compound were obtained by slow evaporation of its concentrated solution in dichloromethane at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C).
For the synthesis of the title compound, see: Reger et al. (2005); Son et al. (2014). For metal complexes with similar ligands, see: Massoud et al. (2013); Sharma et al. (2011); Ojwach et al. (2007); Manikandan et al. (2000, 2001); Halcrow & Kilner (2002); Foster et al. (2002). For the potential applications of the ligand in catalysis, see: Karam et al. (2005).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012). ![]() | Fig. 1. Molecular structure of the title compound, showing the atom-numbering scheme and 30% probability ellipsoids. |
![]() | Fig. 2. Dimer formation via C—H···π interactions. |
[CoCl2(C25H21N5)] | F(000) = 2136 |
Mr = 521.3 | Dx = 1.503 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4379 reflections |
a = 12.9766 (4) Å | θ = 2.4–23.4° |
b = 10.5867 (3) Å | µ = 1.00 mm−1 |
c = 33.5943 (9) Å | T = 296 K |
β = 93.2592 (19)° | Plate, deep-blue |
V = 4607.7 (2) Å3 | 0.25 × 0.22 × 0.1 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 3751 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.072 |
φ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −15→17 |
Tmin = 0.76, Tmax = 0.903 | k = −14→14 |
25697 measured reflections | l = −44→44 |
5718 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.048P)2 + 4.3485P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
5718 reflections | Δρmax = 0.52 e Å−3 |
298 parameters | Δρmin = −0.47 e Å−3 |
[CoCl2(C25H21N5)] | V = 4607.7 (2) Å3 |
Mr = 521.3 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 12.9766 (4) Å | µ = 1.00 mm−1 |
b = 10.5867 (3) Å | T = 296 K |
c = 33.5943 (9) Å | 0.25 × 0.22 × 0.1 mm |
β = 93.2592 (19)° |
Bruker SMART CCD area-detector diffractometer | 5718 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 3751 reflections with I > 2σ(I) |
Tmin = 0.76, Tmax = 0.903 | Rint = 0.072 |
25697 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.52 e Å−3 |
5718 reflections | Δρmin = −0.47 e Å−3 |
298 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Co1 | 0.39083 (3) | 0.22404 (4) | 0.58917 (2) | 0.03468 (14) | |
Cl2 | 0.56212 (7) | 0.23374 (10) | 0.58231 (3) | 0.0500 (2) | |
Cl3 | 0.32167 (10) | 0.40748 (10) | 0.60338 (3) | 0.0672 (3) | |
N4 | 0.3229 (2) | 0.1187 (3) | 0.54406 (7) | 0.0331 (6) | |
N5 | 0.2543 (2) | 0.0299 (3) | 0.55511 (7) | 0.0366 (6) | |
C6 | 0.2331 (3) | −0.0533 (3) | 0.52567 (10) | 0.0443 (9) | |
H6 | 0.1887 | −0.122 | 0.5266 | 0.053* | |
C7 | 0.2884 (3) | −0.0185 (3) | 0.49419 (10) | 0.0436 (9) | |
H7 | 0.2894 | −0.059 | 0.4696 | 0.052* | |
C8 | 0.3435 (3) | 0.0901 (3) | 0.50604 (9) | 0.0347 (7) | |
C9 | 0.4137 (2) | 0.1637 (3) | 0.48268 (9) | 0.0342 (7) | |
C10 | 0.4601 (3) | 0.1057 (4) | 0.45118 (10) | 0.0475 (9) | |
H10 | 0.4465 | 0.021 | 0.4457 | 0.057* | |
C11 | 0.5260 (3) | 0.1714 (4) | 0.42791 (12) | 0.0562 (11) | |
H11 | 0.5554 | 0.1316 | 0.4066 | 0.067* | |
C12 | 0.5480 (3) | 0.2960 (4) | 0.43629 (11) | 0.0534 (11) | |
H12 | 0.5953 | 0.3394 | 0.4216 | 0.064* | |
C13 | 0.5003 (3) | 0.3558 (4) | 0.46622 (11) | 0.0509 (10) | |
H13 | 0.513 | 0.4411 | 0.471 | 0.061* | |
C14 | 0.4333 (3) | 0.2909 (4) | 0.48940 (10) | 0.0436 (9) | |
H14 | 0.4012 | 0.3328 | 0.5096 | 0.052* | |
C15 | 0.2098 (3) | 0.0399 (4) | 0.59390 (9) | 0.0403 (8) | |
H15A | 0.1516 | −0.0174 | 0.5947 | 0.048* | |
H15B | 0.1841 | 0.1251 | 0.5972 | 0.048* | |
C16 | 0.2864 (2) | 0.0096 (3) | 0.62810 (9) | 0.0333 (7) | |
N17 | 0.3619 (2) | 0.0971 (2) | 0.63560 (7) | 0.0314 (6) | |
C18 | 0.4258 (2) | 0.0796 (3) | 0.66823 (9) | 0.0330 (7) | |
C19 | 0.4218 (3) | −0.0281 (4) | 0.69132 (10) | 0.0430 (9) | |
H19 | 0.4689 | −0.0395 | 0.7129 | 0.052* | |
C20 | 0.3486 (3) | −0.1176 (4) | 0.68232 (11) | 0.0492 (10) | |
H20 | 0.346 | −0.1911 | 0.6974 | 0.059* | |
C21 | 0.2784 (3) | −0.0975 (4) | 0.65052 (10) | 0.0438 (9) | |
H21 | 0.2264 | −0.156 | 0.6444 | 0.053* | |
C22 | 0.4977 (3) | 0.1871 (3) | 0.68058 (10) | 0.0364 (8) | |
H22A | 0.5015 | 0.2456 | 0.6585 | 0.044* | |
H22B | 0.4696 | 0.2324 | 0.7026 | 0.044* | |
N23 | 0.6008 (2) | 0.1435 (3) | 0.69249 (8) | 0.0363 (6) | |
C24 | 0.6654 (3) | 0.0790 (3) | 0.67056 (10) | 0.0420 (8) | |
H24 | 0.6533 | 0.0544 | 0.6441 | 0.05* | |
C25 | 0.7519 (3) | 0.0558 (3) | 0.69398 (10) | 0.0436 (9) | |
H25 | 0.8105 | 0.0122 | 0.6871 | 0.052* | |
C26 | 0.7342 (3) | 0.1112 (3) | 0.73064 (9) | 0.0352 (7) | |
N27 | 0.6417 (2) | 0.1659 (3) | 0.72992 (8) | 0.0374 (7) | |
C28 | 0.8065 (3) | 0.1190 (3) | 0.76634 (10) | 0.0376 (8) | |
C29 | 0.8786 (3) | 0.0243 (4) | 0.77423 (12) | 0.0503 (9) | |
H29 | 0.8804 | −0.0454 | 0.7574 | 0.06* | |
C30 | 0.9484 (3) | 0.0329 (4) | 0.80719 (12) | 0.0550 (10) | |
H30 | 0.9961 | −0.0314 | 0.8124 | 0.066* | |
C31 | 0.9473 (3) | 0.1347 (4) | 0.83167 (11) | 0.0557 (11) | |
H31 | 0.9954 | 0.1413 | 0.8532 | 0.067* | |
C32 | 0.8750 (3) | 0.2281 (4) | 0.82467 (12) | 0.0586 (11) | |
H32 | 0.873 | 0.2968 | 0.8419 | 0.07* | |
C33 | 0.8047 (3) | 0.2202 (4) | 0.79195 (11) | 0.0493 (9) | |
H33 | 0.756 | 0.2838 | 0.7874 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0414 (3) | 0.0335 (3) | 0.0290 (2) | −0.0090 (2) | 0.00033 (17) | −0.00083 (19) |
Cl2 | 0.0439 (5) | 0.0617 (6) | 0.0444 (5) | −0.0201 (5) | 0.0022 (4) | 0.0001 (4) |
Cl3 | 0.1011 (9) | 0.0450 (6) | 0.0563 (6) | 0.0149 (6) | 0.0115 (6) | −0.0023 (5) |
N4 | 0.0346 (15) | 0.0383 (16) | 0.0263 (13) | −0.0087 (12) | 0.0011 (11) | −0.0016 (11) |
N5 | 0.0377 (16) | 0.0422 (17) | 0.0297 (13) | −0.0109 (13) | 0.0008 (11) | −0.0011 (12) |
C6 | 0.050 (2) | 0.043 (2) | 0.0392 (19) | −0.0181 (18) | −0.0066 (16) | −0.0034 (16) |
C7 | 0.056 (2) | 0.043 (2) | 0.0309 (17) | −0.0089 (18) | −0.0021 (15) | −0.0078 (15) |
C8 | 0.0377 (18) | 0.039 (2) | 0.0267 (15) | −0.0016 (15) | −0.0035 (13) | −0.0009 (14) |
C9 | 0.0342 (18) | 0.040 (2) | 0.0279 (15) | 0.0005 (15) | −0.0028 (13) | 0.0022 (14) |
C10 | 0.057 (2) | 0.045 (2) | 0.0408 (19) | 0.0037 (19) | 0.0075 (17) | −0.0028 (17) |
C11 | 0.059 (3) | 0.065 (3) | 0.046 (2) | 0.011 (2) | 0.0181 (19) | 0.003 (2) |
C12 | 0.045 (2) | 0.076 (3) | 0.039 (2) | −0.006 (2) | 0.0033 (16) | 0.017 (2) |
C13 | 0.061 (3) | 0.050 (2) | 0.040 (2) | −0.018 (2) | −0.0066 (18) | 0.0047 (17) |
C14 | 0.055 (2) | 0.047 (2) | 0.0291 (16) | −0.0053 (18) | 0.0015 (15) | 0.0001 (15) |
C15 | 0.0321 (18) | 0.056 (2) | 0.0334 (17) | −0.0123 (17) | 0.0030 (13) | 0.0007 (16) |
C16 | 0.0312 (17) | 0.0408 (19) | 0.0287 (15) | −0.0066 (15) | 0.0079 (13) | −0.0017 (14) |
N17 | 0.0319 (14) | 0.0340 (15) | 0.0284 (13) | −0.0035 (12) | 0.0016 (11) | 0.0011 (11) |
C18 | 0.0361 (18) | 0.0368 (19) | 0.0264 (15) | −0.0012 (15) | 0.0028 (13) | −0.0031 (13) |
C19 | 0.046 (2) | 0.050 (2) | 0.0329 (17) | −0.0017 (18) | 0.0001 (15) | 0.0083 (16) |
C20 | 0.058 (3) | 0.041 (2) | 0.049 (2) | −0.0077 (19) | 0.0103 (18) | 0.0156 (17) |
C21 | 0.042 (2) | 0.047 (2) | 0.0427 (19) | −0.0185 (17) | 0.0074 (16) | 0.0024 (16) |
C22 | 0.0421 (19) | 0.0361 (19) | 0.0301 (16) | −0.0028 (15) | −0.0057 (14) | −0.0019 (13) |
N23 | 0.0362 (16) | 0.0415 (17) | 0.0309 (14) | −0.0044 (13) | −0.0016 (11) | −0.0028 (12) |
C24 | 0.045 (2) | 0.045 (2) | 0.0354 (18) | −0.0048 (17) | 0.0015 (15) | −0.0069 (16) |
C25 | 0.041 (2) | 0.043 (2) | 0.047 (2) | −0.0017 (17) | 0.0055 (16) | −0.0038 (16) |
C26 | 0.0341 (18) | 0.0339 (18) | 0.0375 (17) | −0.0085 (15) | −0.0001 (14) | 0.0033 (14) |
N27 | 0.0418 (17) | 0.0408 (17) | 0.0289 (14) | −0.0057 (14) | −0.0035 (12) | 0.0003 (12) |
C28 | 0.0342 (19) | 0.044 (2) | 0.0345 (17) | −0.0067 (16) | 0.0000 (14) | 0.0042 (15) |
C29 | 0.047 (2) | 0.052 (2) | 0.052 (2) | −0.0003 (19) | 0.0010 (18) | −0.0040 (19) |
C30 | 0.042 (2) | 0.064 (3) | 0.059 (2) | 0.003 (2) | −0.0032 (18) | 0.013 (2) |
C31 | 0.050 (2) | 0.073 (3) | 0.042 (2) | −0.013 (2) | −0.0068 (18) | 0.004 (2) |
C32 | 0.067 (3) | 0.061 (3) | 0.047 (2) | −0.004 (2) | −0.0086 (19) | −0.016 (2) |
C33 | 0.049 (2) | 0.046 (2) | 0.052 (2) | 0.0038 (19) | −0.0074 (17) | 0.0010 (18) |
Co1—N4 | 2.041 (3) | C18—C19 | 1.381 (5) |
Co1—N17 | 2.109 (3) | C18—C22 | 1.515 (4) |
Co1—Cl3 | 2.2030 (11) | C19—C20 | 1.364 (5) |
Co1—Cl2 | 2.2499 (10) | C19—H19 | 0.93 |
N4—C8 | 1.354 (4) | C20—C21 | 1.380 (5) |
N4—N5 | 1.361 (4) | C20—H20 | 0.93 |
N5—C6 | 1.341 (4) | C21—H21 | 0.93 |
N5—C15 | 1.459 (4) | C22—N23 | 1.450 (4) |
C6—C7 | 1.362 (5) | C22—H22A | 0.97 |
C6—H6 | 0.93 | C22—H22B | 0.97 |
C7—C8 | 1.400 (5) | N23—C24 | 1.335 (4) |
C7—H7 | 0.93 | N23—N27 | 1.358 (3) |
C8—C9 | 1.461 (5) | C24—C25 | 1.356 (5) |
C9—C14 | 1.386 (5) | C24—H24 | 0.93 |
C9—C10 | 1.390 (5) | C25—C26 | 1.395 (5) |
C10—C11 | 1.378 (5) | C25—H25 | 0.93 |
C10—H10 | 0.93 | C26—N27 | 1.331 (4) |
C11—C12 | 1.376 (6) | C26—C28 | 1.482 (4) |
C11—H11 | 0.93 | C28—C33 | 1.375 (5) |
C12—C13 | 1.366 (6) | C28—C29 | 1.388 (5) |
C12—H12 | 0.93 | C29—C30 | 1.393 (5) |
C13—C14 | 1.383 (5) | C29—H29 | 0.93 |
C13—H13 | 0.93 | C30—C31 | 1.356 (6) |
C14—H14 | 0.93 | C30—H30 | 0.93 |
C15—C16 | 1.510 (4) | C31—C32 | 1.375 (6) |
C15—H15A | 0.97 | C31—H31 | 0.93 |
C15—H15B | 0.97 | C32—C33 | 1.390 (5) |
C16—N17 | 1.361 (4) | C32—H32 | 0.93 |
C16—C21 | 1.369 (5) | C33—H33 | 0.93 |
N17—C18 | 1.349 (4) | ||
N4—Co1—N17 | 96.51 (10) | C16—N17—Co1 | 116.9 (2) |
N4—Co1—Cl3 | 118.60 (9) | N17—C18—C19 | 121.9 (3) |
N17—Co1—Cl3 | 108.05 (8) | N17—C18—C22 | 117.4 (3) |
N4—Co1—Cl2 | 109.65 (8) | C19—C18—C22 | 120.6 (3) |
N17—Co1—Cl2 | 108.85 (8) | C20—C19—C18 | 119.8 (3) |
Cl3—Co1—Cl2 | 113.51 (5) | C20—C19—H19 | 120.1 |
C8—N4—N5 | 105.7 (2) | C18—C19—H19 | 120.1 |
C8—N4—Co1 | 136.3 (2) | C19—C20—C21 | 119.0 (3) |
N5—N4—Co1 | 115.88 (18) | C19—C20—H20 | 120.5 |
C6—N5—N4 | 111.2 (3) | C21—C20—H20 | 120.5 |
C6—N5—C15 | 129.2 (3) | C16—C21—C20 | 119.1 (3) |
N4—N5—C15 | 119.5 (3) | C16—C21—H21 | 120.5 |
N5—C6—C7 | 107.5 (3) | C20—C21—H21 | 120.5 |
N5—C6—H6 | 126.3 | N23—C22—C18 | 112.4 (3) |
C7—C6—H6 | 126.3 | N23—C22—H22A | 109.1 |
C6—C7—C8 | 106.5 (3) | C18—C22—H22A | 109.1 |
C6—C7—H7 | 126.7 | N23—C22—H22B | 109.1 |
C8—C7—H7 | 126.7 | C18—C22—H22B | 109.1 |
N4—C8—C7 | 109.1 (3) | H22A—C22—H22B | 107.9 |
N4—C8—C9 | 123.4 (3) | C24—N23—N27 | 112.0 (3) |
C7—C8—C9 | 127.5 (3) | C24—N23—C22 | 127.5 (3) |
C14—C9—C10 | 118.0 (3) | N27—N23—C22 | 120.4 (3) |
C14—C9—C8 | 123.0 (3) | N23—C24—C25 | 107.3 (3) |
C10—C9—C8 | 118.9 (3) | N23—C24—H24 | 126.3 |
C11—C10—C9 | 121.2 (4) | C25—C24—H24 | 126.3 |
C11—C10—H10 | 119.4 | C24—C25—C26 | 105.3 (3) |
C9—C10—H10 | 119.4 | C24—C25—H25 | 127.4 |
C12—C11—C10 | 119.7 (4) | C26—C25—H25 | 127.4 |
C12—C11—H11 | 120.1 | N27—C26—C25 | 111.1 (3) |
C10—C11—H11 | 120.1 | N27—C26—C28 | 121.2 (3) |
C13—C12—C11 | 119.8 (4) | C25—C26—C28 | 127.5 (3) |
C13—C12—H12 | 120.1 | C26—N27—N23 | 104.2 (3) |
C11—C12—H12 | 120.1 | C33—C28—C29 | 118.6 (3) |
C12—C13—C14 | 120.7 (4) | C33—C28—C26 | 121.2 (3) |
C12—C13—H13 | 119.7 | C29—C28—C26 | 120.2 (3) |
C14—C13—H13 | 119.7 | C28—C29—C30 | 120.4 (4) |
C13—C14—C9 | 120.4 (3) | C28—C29—H29 | 119.8 |
C13—C14—H14 | 119.8 | C30—C29—H29 | 119.8 |
C9—C14—H14 | 119.8 | C31—C30—C29 | 120.4 (4) |
N5—C15—C16 | 112.8 (3) | C31—C30—H30 | 119.8 |
N5—C15—H15A | 109 | C29—C30—H30 | 119.8 |
C16—C15—H15A | 109 | C30—C31—C32 | 119.9 (4) |
N5—C15—H15B | 109 | C30—C31—H31 | 120 |
C16—C15—H15B | 109 | C32—C31—H31 | 120 |
H15A—C15—H15B | 107.8 | C31—C32—C33 | 120.2 (4) |
N17—C16—C21 | 122.5 (3) | C31—C32—H32 | 119.9 |
N17—C16—C15 | 115.6 (3) | C33—C32—H32 | 119.9 |
C21—C16—C15 | 121.8 (3) | C28—C33—C32 | 120.5 (4) |
C18—N17—C16 | 117.4 (3) | C28—C33—H33 | 119.7 |
C18—N17—Co1 | 124.2 (2) | C32—C33—H33 | 119.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···Cg1i | 0.93 | 2.87 | 3.806 (4) | 180 |
Symmetry code: (i) −x+1, −y, −z+1. |
Acknowledgements
Financial support from the National Research Foundation of Korea (NRF-2012R1A1A1005839) is gratefully acknowledged.
References
Bruker (2002). SADABS, SAINT and SMART. 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
Foster, C. L., Kilner, C. A., Thornton-Pett, M. & Halcrow, M. A. (2002). Polyhedron, 21, 1031–1041. Web of Science CSD CrossRef CAS Google Scholar
Halcrow, M. A. & Kilner, C. A. (2002). Acta Cryst. C58, m424–m426. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Karam, A. R., Catarí, E. L., López-Linares, F., Agrifoglio, G., Albano, C. L., Díaz-Barrios, A., Lehmann, T. E., Pekerar, S. V., Albornoz, L. A., Atencio, R., González, T., Ortega, H. B. & Joskowics, P. (2005). Appl. Catal. A, 280, 165–173. Web of Science CrossRef CAS Google Scholar
Manikandan, P., Justin Thomas, K. R. & Manoharan, P. T. (2000). J. Chem. Soc. Dalton Trans. pp. 2779–2785. Web of Science CSD CrossRef Google Scholar
Manikandan, P., Padmakumar, K., Justin Thomas, K. R., Varghese, B., Onodera, H. & Manoharan, P. T. (2001). Inorg. Chem. 40, 6930–6939. Web of Science CSD CrossRef PubMed CAS Google Scholar
Massoud, S. S., Guilbeau, A. E., Luong, H. T., Vicente, R., Albering, J. H., Fischer, R. C. & Mautner, F. A. (2013). Polyhedron, 54, 26–33. Web of Science CSD CrossRef CAS Google Scholar
Ojwach, S. O., Guzei, I. A., Darkwa, J. & Mapolie, S. F. (2007). Polyhedron, 26, 851–861. Web of Science CSD CrossRef CAS Google Scholar
Reger, D. L., Semeniuc, R. F. & Smith, M. D. (2005). Cryst. Growth Des. 5, 1181–1190. Web of Science CSD CrossRef CAS Google Scholar
Sharma, A. K., De, A., Balamurugan, V. & Mukherjee, R. (2011). Inorg. Chim. Acta, 372, 327–332. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Son, K., Woo, J. O., Kim, D. & Kang, S. K. (2014). Acta Cryst. E70, o973. CSD CrossRef IUCr Journals Google Scholar
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