Abstract
In the title complex, [Ni(C14H12N3O)2], the NiII atom lies at the centre of a distorted octahedron formed by two tridentate hydrazone ligands. Intermolecular hydrogen bonds of the type C—H⋯X (X = N, O) link the complexes into a two-dimensional network.
Related literature
For the preparation of the precursor ligand, see: Sen et al. (2005 ▶). For related complexes of the same ligand, see: Sen et al. (2005 ▶, 2007a ▶,b ▶), Ray et al. (2008 ▶).
Experimental
Crystal data
[Ni(C14H12N3O)2]
M r = 535.24
Monoclinic,
a = 10.248 (6) Å
b = 19.692 (11) Å
c = 12.281 (7) Å
β = 91.523 (10)°
V = 2477 (2) Å3
Z = 4
Mo Kα radiation
μ = 0.82 mm−1
T = 298 K
0.37 × 0.33 × 0.25 mm
Data collection
Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.751, T max = 0.821
5679 measured reflections
3600 independent reflections
3352 reflections with I > 2σ
R int = 0.093
Refinement
R[F 2 > 2σ(F 2)] = 0.067
wR(F 2) = 0.182
S = 1.04
3600 reflections
336 parameters
2 restraints
H-atom parameters constrained
Δρmax = 1.05 e Å−3
Δρmin = −0.89 e Å−3
Absolute structure: Flack (1983 ▶), 1156 Friedel pairs
Flack parameter: 0.00 (2)
Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: DIAMOND (Brandenburg, 1999 ▶).
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007336/jh2131sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007336/jh2131Isup2.hkl
Table 1. Hydrogen-bond geometry (Å, °).
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
---|---|---|---|---|
C21—H21B⋯N6 | 0.96 | 2.51 | 2.861 (10) | 102 |
C10—H10⋯N3 | 0.93 | 2.51 | 2.813 (10) | 100 |
C4—H4⋯O1i | 0.93 | 2.51 | 3.164 (8) | 128 |
C18—H18⋯O2ii | 0.93 | 2.39 | 3.300 (9) | 167 |
Symmetry codes: (i) ; (ii) .
Acknowledgments
We are grateful to the National Science Council of Taiwan for financial support.
supplementary crystallographic information
Comment
The title complex adopts a distorted octahedron geometry with two tridentate hydrazone ligands. While the N–Ni–N angle is 174.5 (2)°, which is close to the ideal 180°, the two O–Ni–N angles are much smaller (154.7 (2)° and 153.9 (2)°).
An intramolecular non-classical hydrogen bond of the type C—H···N is present. Non-classical intermolecular hydrogen bonds of type C—H···N and C—H···O also link complexes into a two-dimensional network.
Copper (Sen et al. 2007a)(Sen et al. 2007b), cadmium (Sen et al. 2005), zinc (Ray et al. 2008) and manganese (Ray et al. 2008) complexes of the same ligand have been published.
Experimental
The ligand precursor, [C6H5C(O)NHN=C(CH3)C5H4N] (LH) was prepared according to a literature procedure (Sen et al. 2005). To a methanolic solution (20 ml) of nickel chloride hexahydrate (0.237 g, 1.0 mmol), LH (0.478 g, 2 mmol) was added and then kept at room temperature. After a few days, dark brown, rectangular crystals of the title compound suitable for X-ray diffraction studies were formed. Crystals were collected and dried in the air. Yield: 0.147 g, 62%.
Refinement
All the H atoms were positioned geometrically and refined as riding atoms, with Caryl—H = 0.93, Cmethyl—H = 0.96, Å while Uiso(H) = 1.5 Ueq (C) for the methyl H atoms and 1.2 Ueq (C) for all the other H atoms.
Figures
Crystal data
[Ni(C14H12N3O)2] | F(000) = 1112 |
Mr = 535.24 | Dx = 1.435 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 3920 reflections |
a = 10.248 (6) Å | θ = 2.2–26.3° |
b = 19.692 (11) Å | µ = 0.82 mm−1 |
c = 12.281 (7) Å | T = 298 K |
β = 91.523 (10)° | Parallelepiped, brown |
V = 2477 (2) Å3 | 0.37 × 0.33 × 0.25 mm |
Z = 4 |
Data collection
Bruker SMART APEXII diffractometer | 3600 independent reflections |
Radiation source: fine-focus sealed tube | 3352 reflections with I > 2σ |
graphite | Rint = 0.093 |
ω scans | θmax = 26.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→10 |
Tmin = 0.751, Tmax = 0.821 | k = −22→24 |
5679 measured reflections | l = −15→13 |
Refinement
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.1528P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3600 reflections | Δρmax = 1.05 e Å−3 |
336 parameters | Δρmin = −0.88 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1156 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Flack parameter: 0.00 (2) |
Special details
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x | y | z | Uiso*/Ueq | ||
C1 | 1.1923 (7) | 0.6618 (3) | 0.3808 (6) | 0.0451 (14) | |
H1 | 1.1942 | 0.6524 | 0.4550 | 0.054* | |
C2 | 1.2836 (8) | 0.6300 (4) | 0.3159 (7) | 0.0561 (18) | |
H2 | 1.3456 | 0.6005 | 0.3460 | 0.067* | |
C3 | 1.2791 (7) | 0.6435 (4) | 0.2071 (7) | 0.0552 (18) | |
H3 | 1.3385 | 0.6229 | 0.1616 | 0.066* | |
C4 | 1.1860 (7) | 0.6880 (4) | 0.1640 (6) | 0.0467 (15) | |
H4 | 1.1812 | 0.6968 | 0.0896 | 0.056* | |
C5 | 1.0994 (6) | 0.7192 (3) | 0.2350 (5) | 0.0370 (12) | |
C6 | 1.0010 (7) | 0.7708 (3) | 0.1986 (5) | 0.0404 (14) | |
C7 | 0.9737 (8) | 0.7881 (4) | 0.0812 (5) | 0.0532 (17) | |
H7A | 0.9677 | 0.8365 | 0.0731 | 0.080* | |
H7B | 0.8929 | 0.7676 | 0.0575 | 0.080* | |
H7C | 1.0432 | 0.7712 | 0.0378 | 0.080* | |
C8 | 0.8049 (6) | 0.8668 (3) | 0.3545 (5) | 0.0364 (12) | |
C9 | 0.7033 (7) | 0.9222 (3) | 0.3491 (5) | 0.0400 (13) | |
C10 | 0.6377 (9) | 0.9389 (4) | 0.2532 (7) | 0.064 (2) | |
H10 | 0.6593 | 0.9167 | 0.1893 | 0.076* | |
C11 | 0.5411 (9) | 0.9875 (4) | 0.2496 (7) | 0.067 (2) | |
H11 | 0.4971 | 0.9973 | 0.1843 | 0.080* | |
C12 | 0.5094 (8) | 1.0221 (4) | 0.3453 (7) | 0.0556 (18) | |
H12 | 0.4448 | 1.0553 | 0.3439 | 0.067* | |
C13 | 0.5742 (8) | 1.0065 (3) | 0.4398 (6) | 0.0487 (16) | |
H13 | 0.5536 | 1.0294 | 0.5033 | 0.058* | |
C14 | 0.6709 (7) | 0.9568 (3) | 0.4436 (6) | 0.0473 (15) | |
H14 | 0.7138 | 0.9466 | 0.5093 | 0.057* | |
C15 | 1.2059 (8) | 0.8590 (4) | 0.4491 (6) | 0.0527 (17) | |
H15 | 1.1929 | 0.8680 | 0.3752 | 0.063* | |
C16 | 1.3118 (9) | 0.8881 (4) | 0.5021 (8) | 0.063 (2) | |
H16 | 1.3707 | 0.9146 | 0.4646 | 0.076* | |
C17 | 1.3282 (8) | 0.8767 (4) | 0.6122 (8) | 0.064 (2) | |
H17 | 1.3977 | 0.8967 | 0.6504 | 0.076* | |
C18 | 1.2418 (7) | 0.8358 (3) | 0.6658 (6) | 0.0495 (16) | |
H18 | 1.2515 | 0.8283 | 0.7403 | 0.059* | |
C19 | 1.1398 (6) | 0.8059 (3) | 0.6063 (5) | 0.0360 (12) | |
C20 | 1.0465 (7) | 0.7564 (3) | 0.6536 (5) | 0.0374 (14) | |
C21 | 1.0476 (10) | 0.7429 (4) | 0.7719 (6) | 0.0523 (19) | |
H21A | 1.1219 | 0.7154 | 0.7914 | 0.078* | |
H21B | 0.9691 | 0.7196 | 0.7903 | 0.078* | |
H21C | 1.0528 | 0.7852 | 0.8108 | 0.078* | |
C22 | 0.8200 (6) | 0.6570 (3) | 0.5195 (5) | 0.0358 (12) | |
C23 | 0.7290 (6) | 0.6000 (3) | 0.5351 (5) | 0.0384 (12) | |
C24 | 0.7114 (8) | 0.5723 (4) | 0.6395 (6) | 0.0568 (18) | |
H24 | 0.7605 | 0.5879 | 0.6992 | 0.068* | |
C25 | 0.6194 (10) | 0.5212 (5) | 0.6517 (9) | 0.081 (3) | |
H25 | 0.6088 | 0.5021 | 0.7202 | 0.098* | |
C26 | 0.5425 (10) | 0.4977 (5) | 0.5641 (9) | 0.075 (3) | |
H26 | 0.4785 | 0.4650 | 0.5743 | 0.090* | |
C27 | 0.5632 (8) | 0.5235 (4) | 0.4637 (8) | 0.061 (2) | |
H27 | 0.5155 | 0.5067 | 0.4042 | 0.073* | |
C28 | 0.6546 (7) | 0.5747 (3) | 0.4480 (6) | 0.0462 (14) | |
H28 | 0.6659 | 0.5921 | 0.3785 | 0.055* | |
N1 | 1.1029 (5) | 0.7048 (3) | 0.3422 (4) | 0.0379 (11) | |
N2 | 0.9417 (5) | 0.7980 (3) | 0.2778 (4) | 0.0338 (10) | |
N3 | 0.8495 (6) | 0.8480 (3) | 0.2592 (4) | 0.0414 (11) | |
N4 | 1.1212 (5) | 0.8188 (3) | 0.4977 (4) | 0.0389 (11) | |
N5 | 0.9746 (6) | 0.7265 (2) | 0.5806 (4) | 0.0352 (11) | |
N6 | 0.8911 (5) | 0.6760 (3) | 0.6080 (4) | 0.0373 (11) | |
Ni1 | 0.96750 (6) | 0.76219 (3) | 0.42846 (5) | 0.0314 (2) | |
O1 | 0.8347 (5) | 0.8422 (2) | 0.4467 (4) | 0.0439 (10) | |
O2 | 0.8288 (5) | 0.6838 (2) | 0.4245 (4) | 0.0415 (10) |
Atomic displacement parameters (Å2)
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.027 (3) | 0.057 (3) | 0.052 (4) | 0.004 (3) | 0.000 (3) | −0.001 (3) |
C2 | 0.035 (4) | 0.057 (4) | 0.077 (6) | 0.008 (3) | 0.002 (3) | −0.007 (3) |
C3 | 0.035 (4) | 0.065 (4) | 0.067 (5) | 0.005 (3) | 0.016 (3) | −0.016 (3) |
C4 | 0.033 (4) | 0.062 (4) | 0.045 (4) | −0.004 (3) | 0.012 (3) | −0.010 (3) |
C5 | 0.027 (3) | 0.049 (3) | 0.035 (3) | −0.009 (3) | 0.006 (2) | −0.004 (2) |
C6 | 0.041 (4) | 0.050 (3) | 0.031 (3) | −0.012 (3) | 0.007 (3) | 0.001 (2) |
C7 | 0.057 (5) | 0.072 (4) | 0.030 (3) | −0.007 (4) | 0.004 (3) | 0.005 (3) |
C8 | 0.027 (3) | 0.044 (3) | 0.038 (3) | 0.000 (2) | 0.002 (2) | 0.000 (2) |
C9 | 0.035 (3) | 0.047 (3) | 0.038 (3) | −0.001 (3) | 0.001 (2) | 0.004 (2) |
C10 | 0.068 (6) | 0.068 (4) | 0.055 (4) | 0.027 (4) | −0.009 (4) | 0.000 (3) |
C11 | 0.070 (6) | 0.067 (4) | 0.062 (5) | 0.031 (4) | −0.019 (4) | 0.002 (4) |
C12 | 0.042 (4) | 0.057 (4) | 0.069 (5) | 0.010 (3) | 0.006 (3) | 0.009 (3) |
C13 | 0.051 (4) | 0.051 (3) | 0.045 (4) | 0.001 (3) | 0.010 (3) | 0.002 (3) |
C14 | 0.042 (4) | 0.053 (3) | 0.047 (4) | −0.002 (3) | 0.003 (3) | 0.007 (3) |
C15 | 0.052 (5) | 0.057 (4) | 0.049 (4) | −0.010 (3) | −0.006 (3) | 0.006 (3) |
C16 | 0.050 (5) | 0.055 (4) | 0.085 (6) | −0.018 (4) | −0.001 (4) | 0.004 (4) |
C17 | 0.046 (5) | 0.057 (4) | 0.086 (6) | −0.008 (3) | −0.023 (4) | −0.011 (4) |
C18 | 0.045 (4) | 0.050 (3) | 0.053 (4) | 0.005 (3) | −0.013 (3) | −0.017 (3) |
C19 | 0.022 (3) | 0.042 (3) | 0.044 (3) | 0.011 (2) | −0.003 (2) | −0.005 (2) |
C20 | 0.039 (4) | 0.042 (3) | 0.031 (3) | 0.007 (2) | −0.002 (3) | −0.003 (2) |
C21 | 0.058 (6) | 0.065 (4) | 0.033 (4) | 0.012 (3) | −0.009 (3) | 0.000 (3) |
C22 | 0.029 (3) | 0.047 (3) | 0.031 (3) | 0.005 (2) | 0.004 (2) | −0.002 (2) |
C23 | 0.021 (3) | 0.049 (3) | 0.046 (3) | 0.000 (2) | 0.009 (2) | 0.005 (2) |
C24 | 0.054 (5) | 0.066 (4) | 0.051 (4) | −0.001 (4) | 0.009 (3) | 0.021 (3) |
C25 | 0.079 (7) | 0.088 (6) | 0.079 (7) | −0.016 (5) | 0.025 (6) | 0.028 (5) |
C26 | 0.056 (5) | 0.067 (5) | 0.103 (8) | −0.014 (4) | 0.018 (5) | 0.017 (5) |
C27 | 0.044 (4) | 0.056 (4) | 0.083 (6) | −0.012 (3) | 0.006 (4) | 0.004 (4) |
C28 | 0.031 (3) | 0.051 (3) | 0.057 (4) | −0.007 (3) | 0.002 (3) | −0.001 (3) |
N1 | 0.026 (3) | 0.049 (3) | 0.039 (3) | −0.004 (2) | 0.002 (2) | −0.001 (2) |
N2 | 0.021 (2) | 0.053 (3) | 0.027 (2) | −0.0020 (19) | 0.0042 (17) | 0.0075 (19) |
N3 | 0.036 (3) | 0.052 (3) | 0.036 (3) | 0.004 (2) | 0.002 (2) | 0.009 (2) |
N4 | 0.024 (2) | 0.046 (3) | 0.047 (3) | −0.004 (2) | −0.002 (2) | −0.003 (2) |
N5 | 0.030 (3) | 0.048 (2) | 0.028 (3) | 0.008 (2) | 0.002 (2) | −0.0004 (18) |
N6 | 0.030 (3) | 0.046 (2) | 0.037 (3) | 0.001 (2) | 0.001 (2) | 0.0061 (19) |
Ni1 | 0.0219 (4) | 0.0438 (3) | 0.0284 (4) | −0.0005 (3) | 0.0006 (2) | 0.0020 (3) |
O1 | 0.039 (3) | 0.057 (2) | 0.036 (2) | 0.010 (2) | 0.0046 (19) | 0.0086 (18) |
O2 | 0.036 (3) | 0.056 (2) | 0.032 (2) | −0.0078 (19) | −0.0022 (18) | 0.0039 (17) |
Geometric parameters (Å, °)
C1—N1 | 1.326 (9) | C16—H16 | 0.9300 |
C1—C2 | 1.393 (10) | C17—C18 | 1.378 (12) |
C1—H1 | 0.9300 | C17—H17 | 0.9300 |
C2—C3 | 1.362 (12) | C18—C19 | 1.389 (9) |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.391 (12) | C19—N4 | 1.366 (8) |
C3—H3 | 0.9300 | C19—C20 | 1.493 (9) |
C4—C5 | 1.402 (9) | C20—N5 | 1.288 (9) |
C4—H4 | 0.9300 | C20—C21 | 1.477 (10) |
C5—N1 | 1.346 (8) | C21—H21A | 0.9600 |
C5—C6 | 1.492 (10) | C21—H21B | 0.9600 |
C6—N2 | 1.277 (9) | C21—H21C | 0.9600 |
C6—C7 | 1.501 (9) | C22—O2 | 1.285 (8) |
C7—H7A | 0.9600 | C22—N6 | 1.346 (8) |
C7—H7B | 0.9600 | C22—C23 | 1.476 (9) |
C7—H7C | 0.9600 | C23—C28 | 1.389 (10) |
C8—O1 | 1.262 (8) | C23—C24 | 1.410 (9) |
C8—N3 | 1.321 (8) | C24—C25 | 1.390 (12) |
C8—C9 | 1.508 (9) | C24—H24 | 0.9300 |
C9—C10 | 1.381 (10) | C25—C26 | 1.396 (16) |
C9—C14 | 1.393 (10) | C25—H25 | 0.9300 |
C10—C11 | 1.376 (11) | C26—C27 | 1.355 (13) |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
C11—C12 | 1.404 (12) | C27—C28 | 1.394 (10) |
C11—H11 | 0.9300 | C27—H27 | 0.9300 |
C12—C13 | 1.358 (11) | C28—H28 | 0.9300 |
C12—H12 | 0.9300 | N1—Ni1 | 2.099 (5) |
C13—C14 | 1.393 (10) | N2—N3 | 1.380 (8) |
C13—H13 | 0.9300 | N2—Ni1 | 1.992 (5) |
C14—H14 | 0.9300 | N4—Ni1 | 2.091 (5) |
C15—N4 | 1.329 (9) | N5—N6 | 1.359 (8) |
C15—C16 | 1.375 (12) | N5—Ni1 | 1.995 (5) |
C15—H15 | 0.9300 | Ni1—O1 | 2.098 (5) |
C16—C17 | 1.376 (12) | Ni1—O2 | 2.098 (5) |
N1—C1—C2 | 123.4 (7) | N5—C20—C19 | 112.9 (6) |
N1—C1—H1 | 118.3 | C21—C20—C19 | 120.7 (6) |
C2—C1—H1 | 118.3 | C20—C21—H21A | 109.5 |
C3—C2—C1 | 117.9 (7) | C20—C21—H21B | 109.5 |
C3—C2—H2 | 121.1 | H21A—C21—H21B | 109.5 |
C1—C2—H2 | 121.1 | C20—C21—H21C | 109.5 |
C2—C3—C4 | 120.1 (6) | H21A—C21—H21C | 109.5 |
C2—C3—H3 | 120.0 | H21B—C21—H21C | 109.5 |
C4—C3—H3 | 120.0 | O2—C22—N6 | 124.7 (6) |
C3—C4—C5 | 118.6 (7) | O2—C22—C23 | 119.3 (5) |
C3—C4—H4 | 120.7 | N6—C22—C23 | 116.0 (5) |
C5—C4—H4 | 120.7 | C28—C23—C24 | 118.7 (7) |
N1—C5—C4 | 121.0 (6) | C28—C23—C22 | 120.6 (6) |
N1—C5—C6 | 115.9 (5) | C24—C23—C22 | 120.6 (6) |
C4—C5—C6 | 123.1 (6) | C25—C24—C23 | 118.8 (9) |
N2—C6—C5 | 112.9 (6) | C25—C24—H24 | 120.6 |
N2—C6—C7 | 123.8 (7) | C23—C24—H24 | 120.6 |
C5—C6—C7 | 123.3 (6) | C24—C25—C26 | 121.8 (8) |
C6—C7—H7A | 109.5 | C24—C25—H25 | 119.1 |
C6—C7—H7B | 109.5 | C26—C25—H25 | 119.1 |
H7A—C7—H7B | 109.5 | C27—C26—C25 | 118.6 (8) |
C6—C7—H7C | 109.5 | C27—C26—H26 | 120.7 |
H7A—C7—H7C | 109.5 | C25—C26—H26 | 120.7 |
H7B—C7—H7C | 109.5 | C26—C27—C28 | 121.3 (9) |
O1—C8—N3 | 127.4 (6) | C26—C27—H27 | 119.3 |
O1—C8—C9 | 117.8 (5) | C28—C27—H27 | 119.3 |
N3—C8—C9 | 114.7 (5) | C23—C28—C27 | 120.7 (7) |
C10—C9—C14 | 118.2 (7) | C23—C28—H28 | 119.7 |
C10—C9—C8 | 122.0 (6) | C27—C28—H28 | 119.7 |
C14—C9—C8 | 119.8 (6) | C1—N1—C5 | 119.0 (6) |
C11—C10—C9 | 121.8 (8) | C1—N1—Ni1 | 128.6 (5) |
C11—C10—H10 | 119.1 | C5—N1—Ni1 | 112.3 (4) |
C9—C10—H10 | 119.1 | C6—N2—N3 | 120.7 (5) |
C10—C11—C12 | 119.5 (7) | C6—N2—Ni1 | 120.3 (5) |
C10—C11—H11 | 120.2 | N3—N2—Ni1 | 118.7 (4) |
C12—C11—H11 | 120.2 | C8—N3—N2 | 107.7 (5) |
C13—C12—C11 | 119.2 (7) | C15—N4—C19 | 118.3 (6) |
C13—C12—H12 | 120.4 | C15—N4—Ni1 | 129.0 (5) |
C11—C12—H12 | 120.4 | C19—N4—Ni1 | 112.5 (4) |
C12—C13—C14 | 121.3 (7) | C20—N5—N6 | 120.9 (5) |
C12—C13—H13 | 119.4 | C20—N5—Ni1 | 119.7 (5) |
C14—C13—H13 | 119.4 | N6—N5—Ni1 | 118.8 (4) |
C13—C14—C9 | 120.1 (7) | C22—N6—N5 | 109.5 (5) |
C13—C14—H14 | 120.0 | N2—Ni1—N5 | 174.5 (2) |
C9—C14—H14 | 120.0 | N2—Ni1—N4 | 105.6 (2) |
N4—C15—C16 | 123.5 (7) | N5—Ni1—N4 | 78.4 (2) |
N4—C15—H15 | 118.3 | N2—Ni1—O1 | 76.29 (19) |
C16—C15—H15 | 118.3 | N5—Ni1—O1 | 99.93 (19) |
C15—C16—C17 | 118.2 (7) | N4—Ni1—O1 | 92.3 (2) |
C15—C16—H16 | 120.9 | N2—Ni1—O2 | 99.56 (19) |
C17—C16—H16 | 120.9 | N5—Ni1—O2 | 76.7 (2) |
C16—C17—C18 | 120.1 (7) | N4—Ni1—O2 | 154.7 (2) |
C16—C17—H17 | 120.0 | O1—Ni1—O2 | 96.6 (2) |
C18—C17—H17 | 120.0 | N2—Ni1—N1 | 78.2 (2) |
C17—C18—C19 | 118.7 (7) | N5—Ni1—N1 | 105.9 (2) |
C17—C18—H18 | 120.6 | N4—Ni1—N1 | 89.5 (2) |
C19—C18—H18 | 120.6 | O1—Ni1—N1 | 153.90 (19) |
N4—C19—C18 | 121.2 (6) | O2—Ni1—N1 | 92.8 (2) |
N4—C19—C20 | 115.2 (5) | C8—O1—Ni1 | 109.5 (4) |
C18—C19—C20 | 123.6 (6) | C22—O2—Ni1 | 110.1 (4) |
N5—C20—C21 | 126.3 (7) | ||
N1—C1—C2—C3 | −0.8 (11) | C18—C19—N4—Ni1 | 176.5 (5) |
C1—C2—C3—C4 | 0.3 (11) | C20—C19—N4—Ni1 | −1.5 (6) |
C2—C3—C4—C5 | 1.2 (11) | C21—C20—N5—N6 | −1.5 (10) |
C3—C4—C5—N1 | −2.3 (10) | C19—C20—N5—N6 | 174.9 (5) |
C3—C4—C5—C6 | 176.2 (6) | C21—C20—N5—Ni1 | 170.3 (6) |
N1—C5—C6—N2 | 5.6 (8) | C19—C20—N5—Ni1 | −13.3 (7) |
C4—C5—C6—N2 | −173.0 (6) | O2—C22—N6—N5 | −1.3 (8) |
N1—C5—C6—C7 | −173.6 (6) | C23—C22—N6—N5 | 177.0 (5) |
C4—C5—C6—C7 | 7.8 (10) | C20—N5—N6—C22 | 175.0 (6) |
O1—C8—C9—C10 | −161.4 (7) | Ni1—N5—N6—C22 | 3.1 (6) |
N3—C8—C9—C10 | 16.3 (10) | C6—N2—Ni1—N4 | 92.0 (5) |
O1—C8—C9—C14 | 16.8 (9) | N3—N2—Ni1—N4 | −94.3 (4) |
N3—C8—C9—C14 | −165.5 (6) | C6—N2—Ni1—O1 | −179.5 (5) |
C14—C9—C10—C11 | −1.0 (13) | N3—N2—Ni1—O1 | −5.7 (4) |
C8—C9—C10—C11 | 177.2 (8) | C6—N2—Ni1—O2 | −85.0 (5) |
C9—C10—C11—C12 | 1.2 (14) | N3—N2—Ni1—O2 | 88.7 (4) |
C10—C11—C12—C13 | −0.5 (13) | C6—N2—Ni1—N1 | 5.9 (5) |
C11—C12—C13—C14 | −0.2 (12) | N3—N2—Ni1—N1 | 179.6 (5) |
C12—C13—C14—C9 | 0.3 (11) | C20—N5—Ni1—N4 | 10.0 (5) |
C10—C9—C14—C13 | 0.3 (10) | N6—N5—Ni1—N4 | −178.1 (4) |
C8—C9—C14—C13 | −178.0 (6) | C20—N5—Ni1—O1 | −80.3 (5) |
N4—C15—C16—C17 | −2.3 (13) | N6—N5—Ni1—O1 | 91.6 (4) |
C15—C16—C17—C18 | 1.7 (13) | C20—N5—Ni1—O2 | −174.8 (5) |
C16—C17—C18—C19 | 0.8 (11) | N6—N5—Ni1—O2 | −2.8 (4) |
C17—C18—C19—N4 | −2.8 (9) | C20—N5—Ni1—N1 | 96.1 (5) |
C17—C18—C19—C20 | 175.0 (6) | N6—N5—Ni1—N1 | −91.9 (4) |
N4—C19—C20—N5 | 9.3 (7) | C15—N4—Ni1—N2 | −14.2 (7) |
C18—C19—C20—N5 | −168.7 (6) | C19—N4—Ni1—N2 | 172.2 (4) |
N4—C19—C20—C21 | −174.1 (6) | C15—N4—Ni1—N5 | 169.7 (7) |
C18—C19—C20—C21 | 8.0 (9) | C19—N4—Ni1—N5 | −3.8 (4) |
O2—C22—C23—C28 | 0.9 (9) | C15—N4—Ni1—O1 | −90.6 (6) |
N6—C22—C23—C28 | −177.6 (6) | C19—N4—Ni1—O1 | 95.8 (4) |
O2—C22—C23—C24 | −176.2 (6) | C15—N4—Ni1—O2 | 158.8 (6) |
N6—C22—C23—C24 | 5.4 (9) | C19—N4—Ni1—O2 | −14.7 (7) |
C28—C23—C24—C25 | −0.6 (11) | C15—N4—Ni1—N1 | 63.3 (6) |
C22—C23—C24—C25 | 176.5 (7) | C19—N4—Ni1—N1 | −110.2 (4) |
C23—C24—C25—C26 | −1.3 (14) | C1—N1—Ni1—N2 | 173.1 (6) |
C24—C25—C26—C27 | 3.2 (16) | C5—N1—Ni1—N2 | −2.1 (4) |
C25—C26—C27—C28 | −3.1 (14) | C1—N1—Ni1—N5 | −10.8 (6) |
C24—C23—C28—C27 | 0.8 (10) | C5—N1—Ni1—N5 | 174.0 (4) |
C22—C23—C28—C27 | −176.3 (6) | C1—N1—Ni1—N4 | 67.0 (6) |
C26—C27—C28—C23 | 1.1 (12) | C5—N1—Ni1—N4 | −108.2 (4) |
C2—C1—N1—C5 | −0.3 (10) | C1—N1—Ni1—O1 | 161.2 (5) |
C2—C1—N1—Ni1 | −175.2 (5) | C5—N1—Ni1—O1 | −14.0 (7) |
C4—C5—N1—C1 | 1.8 (9) | C1—N1—Ni1—O2 | −87.8 (6) |
C6—C5—N1—C1 | −176.8 (6) | C5—N1—Ni1—O2 | 97.0 (4) |
C4—C5—N1—Ni1 | 177.6 (5) | N3—C8—O1—Ni1 | −1.3 (8) |
C6—C5—N1—Ni1 | −1.0 (6) | C9—C8—O1—Ni1 | 176.1 (4) |
C5—C6—N2—N3 | 178.5 (5) | N2—Ni1—O1—C8 | 3.6 (4) |
C7—C6—N2—N3 | −2.3 (10) | N5—Ni1—O1—C8 | −172.2 (4) |
C5—C6—N2—Ni1 | −7.9 (7) | N4—Ni1—O1—C8 | 109.1 (4) |
C7—C6—N2—Ni1 | 171.3 (5) | O2—Ni1—O1—C8 | −94.6 (4) |
O1—C8—N3—N2 | −3.2 (9) | N1—Ni1—O1—C8 | 15.6 (7) |
C9—C8—N3—N2 | 179.4 (5) | N6—C22—O2—Ni1 | −0.9 (7) |
C6—N2—N3—C8 | −179.8 (6) | C23—C22—O2—Ni1 | −179.2 (4) |
Ni1—N2—N3—C8 | 6.5 (7) | N2—Ni1—O2—C22 | −173.9 (4) |
C16—C15—N4—C19 | 0.4 (11) | N5—Ni1—O2—C22 | 1.9 (4) |
C16—C15—N4—Ni1 | −172.8 (6) | N4—Ni1—O2—C22 | 12.9 (7) |
C18—C19—N4—C15 | 2.2 (9) | O1—Ni1—O2—C22 | −96.8 (4) |
C20—C19—N4—C15 | −175.8 (6) | N1—Ni1—O2—C22 | 107.6 (4) |
Hydrogen-bond geometry (Å, °)
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21B···N6 | 0.96 | 2.51 | 2.861 (10) | 102 |
C10—H10···N3 | 0.93 | 2.51 | 2.813 (10) | 100 |
C4—H4···O1i | 0.93 | 2.51 | 3.164 (8) | 128 |
C18—H18···O2ii | 0.93 | 2.39 | 3.300 (9) | 167 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z+1/2.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2131).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007336/jh2131sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007336/jh2131Isup2.hkl