Bis{N-(2-hydroxy­benzo­yl)-N′-[1-(2-pyrid­yl)ethyl­idene]hydrazinato}nickel(II)

The title complex, [Ni(C₁₄H₁₂N₃O₂)₂], consists of two deprotonated 2-acetyl­pyridine salicylhydrazone ligands coord­inated to the nickel as N,N′,O-tridentate ligands, forming a neutral complex. The Ni atom lies on a twofold rotation axis. The structure is stabilized by intra­molecular O—H...N hydrogen bonding and π–π stacking inter­actions between the pyridyl and benzene rings, leading to a two-dimensional network in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.064
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   N3      ..       5.13 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2171
           Count of symmetry unique reflns         1160
           Completeness (_total/calc)            187.16%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1011
           Fraction of Friedel pairs measured     0.872
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis{N-(2-hydroxybenzoyl)-N'-[1-(2-pyridyl)ethylidene]hydrazinato}nickel(II)

Crystal data

[Ni(C14H12N3O2)2]	F(000) = 1176
Mr = 567.24	Dx = 1.531 Mg m^−3
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 836 reflections
a = 12.495 (3) Å	θ = 2.2–24.5°
b = 18.672 (4) Å	µ = 0.84 mm^−1
c = 10.549 (2) Å	T = 293 K
V = 2461.2 (9) Å^3	Block, green
Z = 4	0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1934 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.041
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
φ/ω scans	h = −14→12
5887 measured reflections	k = −19→22
2171 independent reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.028P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2171 reflections	Δρmax = 0.31 e Å^−3
178 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.033 (16)

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	1.0000	0.5000	0.66999 (6)	0.03745 (13)
O1	1.01377 (12)	0.41801 (10)	0.53503 (18)	0.0438 (4)
O2	0.71904 (14)	0.33358 (12)	0.4220 (2)	0.0740 (7)
H2B	0.7317	0.3586	0.4841	0.089*
N1	0.92112 (16)	0.55810 (11)	0.8101 (2)	0.0416 (5)
N2	0.85202 (15)	0.46214 (10)	0.6589 (3)	0.0400 (5)
N3	0.83160 (15)	0.41086 (11)	0.5688 (2)	0.0418 (5)
C1	0.9631 (2)	0.60201 (15)	0.8940 (3)	0.0539 (7)
H1A	1.0357	0.6125	0.8885	0.065*
C2	0.9038 (3)	0.63335 (15)	0.9902 (3)	0.0647 (9)
H2A	0.9359	0.6635	1.0492	0.078*
C3	0.7970 (3)	0.61866 (17)	0.9958 (3)	0.0681 (9)
H3B	0.7551	0.6394	1.0586	0.082*
C4	0.7507 (3)	0.57288 (13)	0.9081 (3)	0.0564 (7)
H4A	0.6780	0.5625	0.9111	0.068*
C5	0.8149 (2)	0.54348 (13)	0.8173 (3)	0.0430 (6)
C6	0.7761 (2)	0.49074 (13)	0.7227 (3)	0.0420 (6)
C7	0.6607 (2)	0.47336 (17)	0.7065 (3)	0.0596 (9)
H7A	0.6535	0.4249	0.6774	0.089*
H7B	0.6296	0.5053	0.6454	0.089*
H7C	0.6245	0.4787	0.7862	0.089*
C8	0.9230 (2)	0.39104 (13)	0.5117 (2)	0.0398 (6)
C9	0.9114 (2)	0.33552 (13)	0.4128 (2)	0.0418 (6)
C10	1.0024 (2)	0.30730 (15)	0.3558 (3)	0.0479 (7)
H10A	1.0694	0.3214	0.3850	0.057*
C11	0.9961 (2)	0.25944 (17)	0.2582 (3)	0.0556 (8)
H11A	1.0582	0.2410	0.2221	0.067*
C12	0.8979 (2)	0.23866 (16)	0.2135 (3)	0.0597 (8)
H12A	0.8930	0.2070	0.1456	0.072*
C13	0.8068 (2)	0.26479 (17)	0.2692 (3)	0.0643 (9)
H13A	0.7403	0.2509	0.2380	0.077*
C14	0.8119 (2)	0.31119 (16)	0.3705 (3)	0.0509 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0256 (2)	0.0466 (2)	0.0402 (2)	0.00006 (19)	0.000	0.000
O1	0.0310 (10)	0.0502 (11)	0.0501 (12)	−0.0064 (7)	0.0008 (8)	−0.0080 (9)
O2	0.0340 (12)	0.0920 (16)	0.0962 (18)	−0.0009 (10)	−0.0092 (13)	−0.0339 (15)
N1	0.0399 (13)	0.0419 (12)	0.0429 (13)	0.0058 (10)	0.0039 (10)	0.0033 (11)
N2	0.0299 (10)	0.0455 (10)	0.0445 (12)	−0.0016 (9)	0.0028 (11)	0.0085 (13)
N3	0.0301 (12)	0.0469 (13)	0.0485 (14)	−0.0027 (9)	−0.0007 (10)	−0.0020 (11)
C1	0.0534 (17)	0.0504 (17)	0.058 (2)	0.0048 (14)	−0.0034 (16)	−0.0014 (16)
C2	0.078 (3)	0.062 (2)	0.054 (2)	0.0121 (17)	0.0027 (17)	−0.0116 (17)
C3	0.085 (3)	0.066 (2)	0.053 (2)	0.0236 (18)	0.0205 (17)	−0.0003 (17)
C4	0.0530 (16)	0.0572 (16)	0.0588 (19)	0.0162 (18)	0.0153 (15)	0.0140 (18)
C5	0.0380 (15)	0.0434 (15)	0.0476 (16)	0.0107 (12)	0.0051 (13)	0.0093 (14)
C6	0.0288 (14)	0.0458 (15)	0.0514 (16)	0.0035 (11)	0.0029 (11)	0.0134 (12)
C7	0.0299 (14)	0.0705 (17)	0.078 (3)	0.0001 (13)	0.0051 (14)	0.0124 (16)
C8	0.0349 (14)	0.0437 (14)	0.0409 (16)	−0.0035 (12)	−0.0031 (12)	0.0076 (12)
C9	0.0356 (14)	0.0436 (15)	0.0463 (17)	−0.0029 (11)	−0.0031 (13)	0.0050 (13)
C10	0.0344 (15)	0.0531 (17)	0.0561 (18)	−0.0049 (13)	−0.0046 (13)	−0.0029 (14)
C11	0.0496 (18)	0.0577 (18)	0.060 (2)	−0.0045 (14)	0.0014 (15)	−0.0075 (15)
C12	0.0564 (19)	0.0618 (18)	0.061 (2)	−0.0054 (14)	−0.0070 (15)	−0.0110 (15)
C13	0.0470 (18)	0.070 (2)	0.075 (2)	−0.0050 (15)	−0.0189 (17)	−0.0179 (18)
C14	0.0373 (16)	0.0571 (18)	0.0583 (19)	−0.0019 (13)	−0.0073 (14)	−0.0016 (15)

Geometric parameters (Å, º)

Ni1—N2	1.9830 (19)	C3—H3B	0.9300
Ni1—N2^i	1.9830 (19)	C4—C5	1.364 (4)
Ni1—N1^i	2.081 (2)	C4—H4A	0.9300
Ni1—N1	2.081 (2)	C5—C6	1.484 (4)
Ni1—O1	2.0977 (19)	C6—C7	1.488 (3)
Ni1—O1^i	2.0977 (19)	C7—H7A	0.9600
O1—C8	1.265 (3)	C7—H7B	0.9600
O2—C14	1.347 (3)	C7—H7C	0.9600
O2—H2B	0.8200	C8—C9	1.478 (4)
N1—C1	1.315 (3)	C9—C10	1.389 (4)
N1—C5	1.357 (3)	C9—C14	1.397 (4)
N2—C6	1.280 (3)	C10—C11	1.366 (4)
N2—N3	1.373 (3)	C10—H10A	0.9300
N3—C8	1.343 (3)	C11—C12	1.371 (4)
C1—C2	1.387 (4)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.370 (4)
C2—C3	1.363 (5)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.378 (4)
C3—C4	1.386 (4)	C13—H13A	0.9300
N2—Ni1—N2^i	173.24 (16)	C3—C4—H4A	120.9
N2—Ni1—N1^i	107.31 (9)	N1—C5—C4	122.2 (3)
N2^i—Ni1—N1^i	77.65 (10)	N1—C5—C6	114.5 (2)
N2—Ni1—N1	77.65 (10)	C4—C5—C6	123.2 (3)
N2^i—Ni1—N1	107.31 (9)	N2—C6—C5	112.8 (2)
N1^i—Ni1—N1	89.53 (12)	N2—C6—C7	124.5 (3)
N2—Ni1—O1	77.08 (8)	C5—C6—C7	122.6 (2)
N2^i—Ni1—O1	98.26 (8)	C6—C7—H7A	109.5
N1^i—Ni1—O1	93.59 (8)	C6—C7—H7B	109.5
N1—Ni1—O1	154.31 (7)	H7A—C7—H7B	109.5
N2—Ni1—O1^i	98.26 (8)	C6—C7—H7C	109.5
N2^i—Ni1—O1^i	77.08 (8)	H7A—C7—H7C	109.5
N1^i—Ni1—O1^i	154.31 (7)	H7B—C7—H7C	109.5
N1—Ni1—O1^i	93.59 (8)	O1—C8—N3	124.4 (2)
O1—Ni1—O1^i	94.52 (11)	O1—C8—C9	120.3 (2)
C8—O1—Ni1	110.43 (16)	N3—C8—C9	115.3 (2)
C14—O2—H2B	109.5	C10—C9—C14	117.8 (3)
C1—N1—C5	118.5 (2)	C10—C9—C8	119.5 (2)
C1—N1—Ni1	127.87 (19)	C14—C9—C8	122.7 (2)
C5—N1—Ni1	113.48 (18)	C11—C10—C9	121.8 (3)
C6—N2—N3	121.1 (2)	C11—C10—H10A	119.1
C6—N2—Ni1	120.77 (19)	C9—C10—H10A	119.1
N3—N2—Ni1	117.56 (15)	C10—C11—C12	119.7 (3)
C8—N3—N2	110.17 (19)	C10—C11—H11A	120.1
N1—C1—C2	122.9 (3)	C12—C11—H11A	120.1
N1—C1—H1A	118.6	C13—C12—C11	119.7 (3)
C2—C1—H1A	118.6	C13—C12—H12A	120.2
C3—C2—C1	118.0 (3)	C11—C12—H12A	120.2
C3—C2—H2A	121.0	C12—C13—C14	121.2 (3)
C1—C2—H2A	121.0	C12—C13—H13A	119.4
C2—C3—C4	120.2 (3)	C14—C13—H13A	119.4
C2—C3—H3B	119.9	O2—C14—C13	117.9 (3)
C4—C3—H3B	119.9	O2—C14—C9	122.5 (3)
C5—C4—C3	118.1 (3)	C13—C14—C9	119.6 (3)
C5—C4—H4A	120.9

Symmetry code: (i) −x+2, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N3	0.82	1.82	2.541 (3)	146