


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810007336/jh2131sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810007336/jh2131Isup2.hkl |
CCDC reference: 720076
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.011 Å
- R factor = 0.067
- wR factor = 0.182
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT915_ALERT_3_B Low Friedel Pair Coverage ...................... 46.11 Perc.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 11 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 30 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 46
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.28 From the CIF: _reflns_number_total 3600 Count of symmetry unique reflns 2519 Completeness (_total/calc) 142.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1081 Fraction of Friedel pairs measured 0.429 Are heavy atom types Z>Si present yes PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large.. 0.15 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2 PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and su .. 0.02
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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%.
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.
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: DIAMOND (Brandenburg, 1999).
[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 |
Bruker SMART APEXII diffractometer | 3600 independent reflections |
Radiation source: fine-focus sealed tube | 3352 reflections with I > 2σ |
Graphite monochromator | 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 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 = −0.89 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1156 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (2) |
[Ni(C14H12N3O)2] | V = 2477 (2) Å3 |
Mr = 535.24 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.248 (6) Å | µ = 0.82 mm−1 |
b = 19.692 (11) Å | T = 298 K |
c = 12.281 (7) Å | 0.37 × 0.33 × 0.25 mm |
β = 91.523 (10)° |
Bruker SMART APEXII diffractometer | 3600 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3352 reflections with I > 2σ |
Tmin = 0.751, Tmax = 0.821 | Rint = 0.093 |
5679 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.182 | Δρmax = 1.05 e Å−3 |
S = 1.04 | Δρmin = −0.89 e Å−3 |
3600 reflections | Absolute structure: Flack (1983), 1156 Friedel pairs |
336 parameters | Absolute structure parameter: 0.00 (2) |
2 restraints |
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 | ||
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) |
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) |
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) |
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. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C14H12N3O)2] |
Mr | 535.24 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 298 |
a, b, c (Å) | 10.248 (6), 19.692 (11), 12.281 (7) |
β (°) | 91.523 (10) |
V (Å3) | 2477 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.82 |
Crystal size (mm) | 0.37 × 0.33 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.751, 0.821 |
No. of measured, independent and observed (I > 2σ) reflections | 5679, 3600, 3352 |
Rint | 0.093 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.182, 1.04 |
No. of reflections | 3600 |
No. of parameters | 336 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.05, −0.89 |
Absolute structure | Flack (1983), 1156 Friedel pairs |
Absolute structure parameter | 0.00 (2) |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).
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. |
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.