Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051793/wn2208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051793/wn2208Isup2.hkl |
CCDC reference: 663101
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.097
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (3) 2.86
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
2-(Tri-2-pyridylmethyliminomethyl)phenol (0.183 g, 0.5 mmol) and Ni(ClO4)2·6H2O (0.183 g, 0.5 mmol) were stirred in methanol (10 ml) for 20 min. To this solution was added a solution of NaN3 (0.065 g, 1.0 mmol) in water (2 ml). The mixture was stirred for a further 10 min at room temperature, and then filtered. After keeping the filtrate in air for 3 d, brown plate crystals were formed.
H atoms were placed at calculated positions and refined in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
Nickel complexes with Schiff bases have received much attention in recent years due to their pharmacological and catalytic properties (Borisova et al., 2007; Bruckner et al., 2000). 2-(Tri-2-pyridylmethyliminomethyl)phenol is a potential N4O pentadentate Schiff base ligand and its complexes with copper(II) have been reported (Arnold et al., 2003; Li & Gao, 2007). We report here the crystal structure of the title compound (Fig. 1).
In the mononuclear nickel complex, the environment around the central nickel atom is essentially square-planar, with a maximum deviation of 0.0529 (32) Å for atom N3. Three of the coordination sites are occupied by the phenolate O1, imine N2 and pyridine N1 atoms of the Schiff base ligand and the fourth site by the terminal N atom of an azide ligand. The other two N atoms of the pyridine rings in the Schiff base are distant from the metal. The Ni1—N1 (pyridine) distance is appreciably longer than that for Ni1—N2 (imine), and the Ni—N3 (azide) distance is almost the same as that found in azido{N-[2-(N,N-diethylamino)ethyl]salicylideneiminato}nickel(II) [1.901 (2) Å] (Mondal et al., 2001) and azido{2,4-dibromo-6-[(2-diethylaminoethylimino)methyl]phenolato}nickel(II) [1.897 (3) Å] (Li et al., 2007).
For related literature, see: Arnold et al. (2003); Borisova et al. (2007); Bruckner et al. (2000); Li & Gao (2007); Li et al. (2007); Mondal et al. (2001).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. |
[Ni(C23H17N4O)(N3)] | F(000) = 960 |
Mr = 466.15 | Dx = 1.547 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2703 reflections |
a = 10.7977 (12) Å | θ = 2.2–25.0° |
b = 14.9156 (16) Å | µ = 1.00 mm−1 |
c = 12.7543 (14) Å | T = 295 K |
β = 103.044 (2)° | Plate, brown |
V = 2001.1 (4) Å3 | 0.10 × 0.08 × 0.04 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 3723 independent reflections |
Radiation source: fine-focus sealed tube | 2616 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 25.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→12 |
Tmin = 0.906, Tmax = 0.966 | k = −18→17 |
14754 measured reflections | l = −15→15 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3 |
3723 reflections | (Δ/σ)max = 0.001 |
289 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
[Ni(C23H17N4O)(N3)] | V = 2001.1 (4) Å3 |
Mr = 466.15 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.7977 (12) Å | µ = 1.00 mm−1 |
b = 14.9156 (16) Å | T = 295 K |
c = 12.7543 (14) Å | 0.10 × 0.08 × 0.04 mm |
β = 103.044 (2)° |
Bruker APEX area-detector diffractometer | 3723 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 2616 reflections with I > 2σ(I) |
Tmin = 0.906, Tmax = 0.966 | Rint = 0.081 |
14754 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.48 e Å−3 |
3723 reflections | Δρmin = −0.63 e Å−3 |
289 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. |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.82925 (4) | 0.91145 (3) | 0.74918 (3) | 0.03162 (15) | |
N1 | 1.0057 (2) | 0.93353 (17) | 0.78930 (19) | 0.0319 (6) | |
N2 | 0.8733 (2) | 0.81489 (16) | 0.67416 (19) | 0.0292 (6) | |
N3 | 0.7952 (3) | 1.0088 (2) | 0.8344 (3) | 0.0571 (9) | |
N4 | 0.6969 (3) | 1.01342 (19) | 0.8625 (2) | 0.0430 (8) | |
N5 | 0.6054 (3) | 1.0224 (2) | 0.8930 (2) | 0.0580 (9) | |
N6 | 1.1723 (3) | 0.6869 (2) | 0.7657 (2) | 0.0490 (8) | |
N7 | 1.0587 (3) | 0.8768 (2) | 0.5391 (2) | 0.0439 (7) | |
O1 | 0.6589 (2) | 0.89314 (15) | 0.70908 (18) | 0.0417 (6) | |
C1 | 1.0501 (3) | 0.7098 (2) | 0.7556 (2) | 0.0336 (8) | |
C2 | 0.9695 (4) | 0.6632 (2) | 0.8061 (3) | 0.0430 (9) | |
H2 | 0.8847 | 0.6799 | 0.7963 | 0.052* | |
C3 | 1.0169 (4) | 0.5915 (3) | 0.8713 (3) | 0.0540 (10) | |
H3 | 0.9639 | 0.5587 | 0.9051 | 0.065* | |
C4 | 1.1417 (4) | 0.5694 (2) | 0.8856 (3) | 0.0578 (11) | |
H4 | 1.1761 | 0.5222 | 0.9306 | 0.069* | |
C5 | 1.2157 (4) | 0.6183 (3) | 0.8320 (3) | 0.0586 (11) | |
H5 | 1.3011 | 0.6030 | 0.8423 | 0.070* | |
C6 | 1.0479 (3) | 0.7177 (2) | 0.5191 (3) | 0.0387 (8) | |
H6 | 1.0390 | 0.6619 | 0.5492 | 0.046* | |
C7 | 1.0655 (3) | 0.7244 (3) | 0.4155 (3) | 0.0509 (10) | |
H7 | 1.0661 | 0.6734 | 0.3737 | 0.061* | |
C8 | 1.0819 (4) | 0.8081 (3) | 0.3753 (3) | 0.0545 (11) | |
H8 | 1.0963 | 0.8146 | 0.3065 | 0.065* | |
C9 | 1.0765 (4) | 0.8817 (3) | 0.4388 (3) | 0.0556 (11) | |
H9 | 1.0858 | 0.9381 | 0.4105 | 0.067* | |
C10 | 1.0438 (3) | 0.7951 (2) | 0.5771 (2) | 0.0334 (8) | |
C11 | 1.0124 (3) | 0.7957 (2) | 0.6893 (2) | 0.0313 (7) | |
C12 | 1.0804 (3) | 0.8732 (2) | 0.7551 (2) | 0.0311 (7) | |
C13 | 1.2115 (3) | 0.8817 (2) | 0.7806 (3) | 0.0401 (9) | |
H13 | 1.2619 | 0.8394 | 0.7564 | 0.048* | |
C14 | 1.2667 (3) | 0.9531 (2) | 0.8417 (3) | 0.0443 (9) | |
H14 | 1.3547 | 0.9596 | 0.8595 | 0.053* | |
C15 | 1.1901 (3) | 1.0148 (2) | 0.8761 (3) | 0.0451 (9) | |
H15 | 1.2254 | 1.0638 | 0.9173 | 0.054* | |
C16 | 1.0610 (3) | 1.0032 (2) | 0.8490 (3) | 0.0407 (9) | |
H16 | 1.0095 | 1.0450 | 0.8728 | 0.049* | |
C17 | 0.7940 (3) | 0.7606 (2) | 0.6136 (2) | 0.0324 (8) | |
H17 | 0.8282 | 0.7152 | 0.5788 | 0.039* | |
C18 | 0.6602 (3) | 0.7650 (2) | 0.5961 (2) | 0.0299 (7) | |
C19 | 0.5858 (3) | 0.7001 (2) | 0.5293 (2) | 0.0349 (8) | |
H19 | 0.6258 | 0.6570 | 0.4958 | 0.042* | |
C20 | 0.4565 (3) | 0.6994 (2) | 0.5130 (3) | 0.0394 (8) | |
H20 | 0.4087 | 0.6560 | 0.4694 | 0.047* | |
C21 | 0.3973 (3) | 0.7644 (2) | 0.5625 (3) | 0.0430 (9) | |
H21 | 0.3091 | 0.7643 | 0.5514 | 0.052* | |
C22 | 0.4660 (3) | 0.8284 (2) | 0.6270 (3) | 0.0398 (9) | |
H22 | 0.4240 | 0.8711 | 0.6595 | 0.048* | |
C23 | 0.5989 (3) | 0.8307 (2) | 0.6451 (2) | 0.0306 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0290 (2) | 0.0333 (2) | 0.0331 (2) | 0.0004 (2) | 0.00817 (17) | −0.0062 (2) |
N1 | 0.0310 (15) | 0.0362 (16) | 0.0292 (15) | −0.0020 (13) | 0.0085 (12) | −0.0003 (12) |
N2 | 0.0279 (15) | 0.0329 (15) | 0.0278 (14) | 0.0004 (12) | 0.0084 (12) | −0.0035 (12) |
N3 | 0.0398 (19) | 0.058 (2) | 0.076 (2) | −0.0026 (17) | 0.0191 (18) | −0.0313 (18) |
N4 | 0.044 (2) | 0.0416 (18) | 0.0398 (18) | 0.0105 (16) | 0.0026 (16) | −0.0104 (14) |
N5 | 0.050 (2) | 0.074 (2) | 0.052 (2) | 0.0180 (19) | 0.0171 (17) | −0.0061 (17) |
N6 | 0.0415 (19) | 0.0527 (19) | 0.0504 (19) | 0.0136 (16) | 0.0052 (15) | 0.0003 (16) |
N7 | 0.0504 (19) | 0.0499 (19) | 0.0327 (16) | −0.0009 (15) | 0.0122 (14) | 0.0014 (14) |
O1 | 0.0330 (13) | 0.0443 (15) | 0.0483 (14) | −0.0006 (11) | 0.0105 (11) | −0.0147 (11) |
C1 | 0.036 (2) | 0.037 (2) | 0.0279 (18) | −0.0005 (16) | 0.0066 (15) | −0.0089 (14) |
C2 | 0.049 (2) | 0.044 (2) | 0.038 (2) | −0.0021 (18) | 0.0119 (17) | −0.0045 (17) |
C3 | 0.079 (3) | 0.045 (2) | 0.036 (2) | −0.005 (2) | 0.011 (2) | 0.0035 (19) |
C4 | 0.083 (3) | 0.035 (2) | 0.048 (2) | 0.009 (2) | −0.002 (2) | 0.0028 (18) |
C5 | 0.054 (3) | 0.055 (3) | 0.059 (3) | 0.015 (2) | −0.004 (2) | −0.009 (2) |
C6 | 0.033 (2) | 0.050 (2) | 0.036 (2) | −0.0004 (17) | 0.0116 (16) | −0.0067 (16) |
C7 | 0.040 (2) | 0.074 (3) | 0.040 (2) | −0.002 (2) | 0.0112 (18) | −0.020 (2) |
C8 | 0.053 (3) | 0.082 (3) | 0.030 (2) | −0.003 (2) | 0.0112 (18) | −0.001 (2) |
C9 | 0.062 (3) | 0.067 (3) | 0.039 (2) | −0.003 (2) | 0.015 (2) | 0.012 (2) |
C10 | 0.0247 (18) | 0.046 (2) | 0.0292 (18) | −0.0002 (16) | 0.0064 (14) | −0.0043 (16) |
C11 | 0.0262 (18) | 0.0382 (19) | 0.0301 (18) | −0.0003 (15) | 0.0077 (14) | −0.0028 (15) |
C12 | 0.0300 (18) | 0.0384 (19) | 0.0258 (17) | −0.0005 (15) | 0.0085 (14) | 0.0009 (14) |
C13 | 0.0321 (19) | 0.050 (2) | 0.043 (2) | −0.0024 (17) | 0.0181 (16) | −0.0057 (17) |
C14 | 0.030 (2) | 0.056 (2) | 0.045 (2) | −0.0094 (18) | 0.0048 (16) | −0.0035 (19) |
C15 | 0.042 (2) | 0.045 (2) | 0.047 (2) | −0.0138 (18) | 0.0086 (18) | −0.0084 (17) |
C16 | 0.046 (2) | 0.037 (2) | 0.039 (2) | −0.0041 (17) | 0.0096 (17) | −0.0108 (16) |
C17 | 0.0335 (19) | 0.0335 (19) | 0.0318 (18) | 0.0014 (15) | 0.0103 (15) | −0.0045 (15) |
C18 | 0.0290 (18) | 0.0352 (19) | 0.0244 (16) | 0.0012 (15) | 0.0037 (14) | 0.0044 (14) |
C19 | 0.035 (2) | 0.041 (2) | 0.0277 (18) | −0.0020 (16) | 0.0051 (15) | −0.0006 (15) |
C20 | 0.037 (2) | 0.045 (2) | 0.0331 (19) | −0.0087 (17) | 0.0019 (16) | 0.0004 (16) |
C21 | 0.0291 (19) | 0.057 (2) | 0.040 (2) | −0.0065 (18) | 0.0025 (16) | 0.0038 (18) |
C22 | 0.031 (2) | 0.051 (2) | 0.040 (2) | 0.0043 (17) | 0.0106 (16) | −0.0003 (17) |
C23 | 0.0303 (19) | 0.0327 (19) | 0.0294 (17) | −0.0007 (15) | 0.0082 (14) | 0.0030 (15) |
Ni1—O1 | 1.815 (2) | C7—C8 | 1.376 (5) |
Ni1—N1 | 1.887 (3) | C7—H7 | 0.9300 |
Ni1—N2 | 1.850 (2) | C8—C9 | 1.373 (5) |
Ni1—N3 | 1.898 (3) | C8—H8 | 0.9300 |
N1—C12 | 1.345 (4) | C9—H9 | 0.9300 |
N1—C16 | 1.345 (4) | C10—C11 | 1.543 (4) |
N2—C17 | 1.298 (4) | C11—C12 | 1.517 (4) |
N2—C11 | 1.498 (4) | C12—C13 | 1.385 (4) |
N3—N4 | 1.197 (4) | C13—C14 | 1.374 (4) |
N4—N5 | 1.148 (4) | C13—H13 | 0.9300 |
N6—C1 | 1.340 (4) | C14—C15 | 1.374 (5) |
N6—C5 | 1.343 (5) | C14—H14 | 0.9300 |
N7—C10 | 1.335 (4) | C15—C16 | 1.370 (4) |
N7—C9 | 1.339 (4) | C15—H15 | 0.9300 |
O1—C23 | 1.309 (3) | C16—H16 | 0.9300 |
C1—C2 | 1.382 (4) | C17—C18 | 1.413 (4) |
C1—C11 | 1.540 (4) | C17—H17 | 0.9300 |
C2—C3 | 1.380 (5) | C18—C23 | 1.407 (4) |
C2—H2 | 0.9300 | C18—C19 | 1.414 (4) |
C3—C4 | 1.360 (5) | C19—C20 | 1.364 (4) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.373 (5) | C20—C21 | 1.390 (5) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.366 (4) |
C6—C10 | 1.377 (4) | C21—H21 | 0.9300 |
C6—C7 | 1.381 (4) | C22—C23 | 1.401 (4) |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
O1—Ni1—N2 | 95.71 (10) | N7—C10—C11 | 113.6 (3) |
O1—Ni1—N1 | 178.50 (11) | C6—C10—C11 | 122.9 (3) |
N2—Ni1—N1 | 85.09 (11) | N2—C11—C12 | 105.8 (2) |
O1—Ni1—N3 | 87.79 (11) | N2—C11—C1 | 111.3 (2) |
N2—Ni1—N3 | 175.69 (13) | C12—C11—C1 | 107.1 (2) |
N1—Ni1—N3 | 91.46 (12) | N2—C11—C10 | 107.8 (2) |
C12—N1—C16 | 118.6 (3) | C12—C11—C10 | 109.7 (3) |
C12—N1—Ni1 | 116.0 (2) | C1—C11—C10 | 114.7 (3) |
C16—N1—Ni1 | 125.4 (2) | N1—C12—C13 | 121.3 (3) |
C17—N2—C11 | 117.7 (3) | N1—C12—C11 | 116.0 (3) |
C17—N2—Ni1 | 125.6 (2) | C13—C12—C11 | 122.8 (3) |
C11—N2—Ni1 | 116.70 (19) | C14—C13—C12 | 119.6 (3) |
N4—N3—Ni1 | 121.0 (2) | C14—C13—H13 | 120.2 |
N5—N4—N3 | 175.9 (4) | C12—C13—H13 | 120.2 |
C1—N6—C5 | 116.8 (3) | C13—C14—C15 | 119.0 (3) |
C10—N7—C9 | 116.9 (3) | C13—C14—H14 | 120.5 |
C23—O1—Ni1 | 127.6 (2) | C15—C14—H14 | 120.5 |
N6—C1—C2 | 122.5 (3) | C16—C15—C14 | 119.1 (3) |
N6—C1—C11 | 113.4 (3) | C16—C15—H15 | 120.5 |
C2—C1—C11 | 123.9 (3) | C14—C15—H15 | 120.5 |
C3—C2—C1 | 118.9 (4) | N1—C16—C15 | 122.5 (3) |
C3—C2—H2 | 120.5 | N1—C16—H16 | 118.8 |
C1—C2—H2 | 120.5 | C15—C16—H16 | 118.8 |
C4—C3—C2 | 119.4 (4) | N2—C17—C18 | 125.3 (3) |
C4—C3—H3 | 120.3 | N2—C17—H17 | 117.3 |
C2—C3—H3 | 120.3 | C18—C17—H17 | 117.3 |
C3—C4—C5 | 118.3 (4) | C23—C18—C17 | 122.0 (3) |
C3—C4—H4 | 120.8 | C23—C18—C19 | 119.0 (3) |
C5—C4—H4 | 120.8 | C17—C18—C19 | 119.0 (3) |
N6—C5—C4 | 124.0 (4) | C20—C19—C18 | 121.3 (3) |
N6—C5—H5 | 118.0 | C20—C19—H19 | 119.3 |
C4—C5—H5 | 118.0 | C18—C19—H19 | 119.3 |
C10—C6—C7 | 118.8 (3) | C19—C20—C21 | 119.1 (3) |
C10—C6—H6 | 120.6 | C19—C20—H20 | 120.5 |
C7—C6—H6 | 120.6 | C21—C20—H20 | 120.5 |
C8—C7—C6 | 118.6 (3) | C22—C21—C20 | 121.2 (3) |
C8—C7—H7 | 120.7 | C22—C21—H21 | 119.4 |
C6—C7—H7 | 120.7 | C20—C21—H21 | 119.4 |
C9—C8—C7 | 118.7 (3) | C21—C22—C23 | 120.9 (3) |
C9—C8—H8 | 120.7 | C21—C22—H22 | 119.6 |
C7—C8—H8 | 120.7 | C23—C22—H22 | 119.6 |
N7—C9—C8 | 123.7 (4) | O1—C23—C22 | 117.7 (3) |
N7—C9—H9 | 118.2 | O1—C23—C18 | 123.8 (3) |
C8—C9—H9 | 118.2 | C22—C23—C18 | 118.5 (3) |
N7—C10—C6 | 123.3 (3) | ||
N2—Ni1—N1—C12 | −3.4 (2) | N7—C10—C11—N2 | 80.5 (3) |
N3—Ni1—N1—C12 | 174.0 (2) | C6—C10—C11—N2 | −95.5 (3) |
N2—Ni1—N1—C16 | 177.2 (3) | N7—C10—C11—C12 | −34.3 (4) |
N3—Ni1—N1—C16 | −5.4 (3) | C6—C10—C11—C12 | 149.7 (3) |
O1—Ni1—N2—C17 | 1.9 (3) | N7—C10—C11—C1 | −154.9 (3) |
N1—Ni1—N2—C17 | −176.8 (3) | C6—C10—C11—C1 | 29.1 (4) |
O1—Ni1—N2—C11 | −175.1 (2) | C16—N1—C12—C13 | 0.2 (4) |
N1—Ni1—N2—C11 | 6.2 (2) | Ni1—N1—C12—C13 | −179.2 (2) |
O1—Ni1—N3—N4 | 21.3 (3) | C16—N1—C12—C11 | 179.3 (3) |
N1—Ni1—N3—N4 | −160.0 (3) | Ni1—N1—C12—C11 | −0.1 (3) |
N2—Ni1—O1—C23 | −1.5 (3) | N2—C11—C12—N1 | 4.5 (3) |
N3—Ni1—O1—C23 | −179.0 (3) | C1—C11—C12—N1 | −114.3 (3) |
C5—N6—C1—C2 | −3.0 (5) | C10—C11—C12—N1 | 120.6 (3) |
C5—N6—C1—C11 | 173.1 (3) | N2—C11—C12—C13 | −176.4 (3) |
N6—C1—C2—C3 | 1.4 (5) | C1—C11—C12—C13 | 64.8 (4) |
C11—C1—C2—C3 | −174.3 (3) | C10—C11—C12—C13 | −60.3 (4) |
C1—C2—C3—C4 | 1.0 (5) | N1—C12—C13—C14 | −0.1 (5) |
C2—C3—C4—C5 | −1.6 (5) | C11—C12—C13—C14 | −179.2 (3) |
C1—N6—C5—C4 | 2.5 (5) | C12—C13—C14—C15 | −0.1 (5) |
C3—C4—C5—N6 | −0.2 (6) | C13—C14—C15—C16 | 0.3 (5) |
C10—C6—C7—C8 | 1.9 (5) | C12—N1—C16—C15 | 0.0 (5) |
C6—C7—C8—C9 | −1.8 (6) | Ni1—N1—C16—C15 | 179.4 (2) |
C10—N7—C9—C8 | −0.9 (5) | C14—C15—C16—N1 | −0.3 (5) |
C7—C8—C9—N7 | 1.4 (6) | C11—N2—C17—C18 | 175.7 (3) |
C9—N7—C10—C6 | 1.0 (5) | Ni1—N2—C17—C18 | −1.3 (4) |
C9—N7—C10—C11 | −175.0 (3) | N2—C17—C18—C23 | −0.3 (5) |
C7—C6—C10—N7 | −1.5 (5) | N2—C17—C18—C19 | −178.9 (3) |
C7—C6—C10—C11 | 174.1 (3) | C23—C18—C19—C20 | −1.0 (4) |
C17—N2—C11—C12 | 175.5 (2) | C17—C18—C19—C20 | 177.6 (3) |
Ni1—N2—C11—C12 | −7.3 (3) | C18—C19—C20—C21 | 0.6 (5) |
C17—N2—C11—C1 | −68.4 (3) | C19—C20—C21—C22 | −0.2 (5) |
Ni1—N2—C11—C1 | 108.8 (2) | C20—C21—C22—C23 | 0.3 (5) |
C17—N2—C11—C10 | 58.2 (3) | Ni1—O1—C23—C22 | 178.8 (2) |
Ni1—N2—C11—C10 | −124.6 (2) | Ni1—O1—C23—C18 | 0.5 (4) |
N6—C1—C11—N2 | 176.2 (2) | C21—C22—C23—O1 | −179.0 (3) |
C2—C1—C11—N2 | −7.8 (4) | C21—C22—C23—C18 | −0.7 (5) |
N6—C1—C11—C12 | −68.6 (3) | C17—C18—C23—O1 | 0.7 (5) |
C2—C1—C11—C12 | 107.5 (3) | C19—C18—C23—O1 | 179.3 (3) |
N6—C1—C11—C10 | 53.4 (3) | C17—C18—C23—C22 | −177.5 (3) |
C2—C1—C11—C10 | −130.5 (3) | C19—C18—C23—C22 | 1.0 (4) |
Experimental details
Crystal data | |
Chemical formula | [Ni(C23H17N4O)(N3)] |
Mr | 466.15 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 10.7977 (12), 14.9156 (16), 12.7543 (14) |
β (°) | 103.044 (2) |
V (Å3) | 2001.1 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.00 |
Crystal size (mm) | 0.10 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.906, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14754, 3723, 2616 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.097, 0.94 |
No. of reflections | 3723 |
No. of parameters | 289 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.63 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).
Ni1—O1 | 1.815 (2) | Ni1—N2 | 1.850 (2) |
Ni1—N1 | 1.887 (3) | Ni1—N3 | 1.898 (3) |
O1—Ni1—N2 | 95.71 (10) | O1—Ni1—N3 | 87.79 (11) |
O1—Ni1—N1 | 178.50 (11) | N2—Ni1—N3 | 175.69 (13) |
N2—Ni1—N1 | 85.09 (11) | N1—Ni1—N3 | 91.46 (12) |
Nickel complexes with Schiff bases have received much attention in recent years due to their pharmacological and catalytic properties (Borisova et al., 2007; Bruckner et al., 2000). 2-(Tri-2-pyridylmethyliminomethyl)phenol is a potential N4O pentadentate Schiff base ligand and its complexes with copper(II) have been reported (Arnold et al., 2003; Li & Gao, 2007). We report here the crystal structure of the title compound (Fig. 1).
In the mononuclear nickel complex, the environment around the central nickel atom is essentially square-planar, with a maximum deviation of 0.0529 (32) Å for atom N3. Three of the coordination sites are occupied by the phenolate O1, imine N2 and pyridine N1 atoms of the Schiff base ligand and the fourth site by the terminal N atom of an azide ligand. The other two N atoms of the pyridine rings in the Schiff base are distant from the metal. The Ni1—N1 (pyridine) distance is appreciably longer than that for Ni1—N2 (imine), and the Ni—N3 (azide) distance is almost the same as that found in azido{N-[2-(N,N-diethylamino)ethyl]salicylideneiminato}nickel(II) [1.901 (2) Å] (Mondal et al., 2001) and azido{2,4-dibromo-6-[(2-diethylaminoethylimino)methyl]phenolato}nickel(II) [1.897 (3) Å] (Li et al., 2007).