trans-Bis(N'-isopropyl-idene-benzo-hydrazidato-κN',O)bis-(pyridine-κN)nickel(II).

The complex mol-ecule of the title compound, [Ni(C(10)H(11)N(2)O)(2)(C(5)H(5)N)(2)], has a crystallographically imposed centre of symmetry. The Ni(II) atom is coordinated in a distorted octa-hedral geometry by the O and N atoms of two trans arranged anionic bidentate hydrazone ligands forming the equatorial plane and by the N atoms of two pyridine mol-ecules at the axial positions. In the crystal, inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into columns parallel to the b axis.

Related literature

For the biological and coordination properties of aroylhydrazones, see: Ali et al. (2004 ▶); Carcelli et al. (1995 ▶); Cheng et al. (1996 ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

[Ni(C10H11N2O)2(C5H5N)2]

M = 567.33

Monoclinic,

a = 15.419 (5) Å

b = 9.242 (3) Å

c = 21.295 (9) Å

β = 109.924 (5)°

V = 2853.1 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.72 mm−1

T = 298 K

0.23 × 0.14 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.852, T max = 0.919

7093 measured reflections

2514 independent reflections

2285 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.078

S = 1.10

2514 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024214/rz2613sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024214/rz2613Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C10H11N2O)2(C5H5N)2]	F(000) = 1192
Mr = 567.33	Dx = 1.321 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5423 reflections
a = 15.419 (5) Å	θ = 2.6–28.5°
b = 9.242 (3) Å	µ = 0.72 mm−1
c = 21.295 (9) Å	T = 298 K
β = 109.924 (5)°	Block, red
V = 2853.1 (18) Å3	0.23 × 0.14 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2514 independent reflections
Radiation source: fine-focus sealed tube	2285 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→16
Tmin = 0.852, Tmax = 0.919	k = −10→8
7093 measured reflections	l = −24→25

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0334P)2 + 2.5175P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2514 reflections	Δρmax = 0.24 e Å−3
178 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0113 (15)

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	0.0000	0.5000	0.0000	0.03337 (12)
O1	0.12440 (8)	0.44811 (14)	0.06671 (6)	0.0385 (3)
N1	0.04126 (10)	0.34430 (16)	0.12653 (8)	0.0393 (4)
N2	−0.03583 (10)	0.40836 (16)	0.07882 (7)	0.0375 (3)
N3	0.00804 (10)	0.71169 (16)	0.04278 (7)	0.0383 (3)
C1	0.28411 (15)	0.3172 (3)	0.14883 (12)	0.0636 (6)
H1	0.2865	0.3759	0.1140	0.076*
C2	0.36373 (18)	0.2488 (4)	0.18906 (15)	0.0871 (9)
H2	0.4190	0.2619	0.1812	0.104*
C3	0.36080 (19)	0.1624 (3)	0.23998 (14)	0.0788 (8)
H3	0.4138	0.1154	0.2668	0.095*
C4	0.27956 (18)	0.1450 (3)	0.25151 (12)	0.0665 (7)
H4	0.2775	0.0861	0.2864	0.080*
C5	0.20085 (15)	0.2138 (2)	0.21199 (10)	0.0504 (5)
H5	0.1462	0.2020	0.2208	0.061*
C6	0.20201 (13)	0.2999 (2)	0.15964 (9)	0.0397 (4)
C7	0.11672 (12)	0.37097 (18)	0.11420 (9)	0.0348 (4)
C8	−0.11104 (14)	0.3927 (2)	0.09097 (10)	0.0474 (5)
C9	−0.11699 (18)	0.3144 (3)	0.15068 (13)	0.0741 (8)
H9A	−0.1454	0.2217	0.1373	0.111*
H9B	−0.1534	0.3699	0.1707	0.111*
H9C	−0.0561	0.3012	0.1825	0.111*
C10	−0.19837 (15)	0.4545 (3)	0.04456 (13)	0.0654 (6)
H10A	−0.1871	0.4978	0.0071	0.098*
H10B	−0.2210	0.5267	0.0675	0.098*
H10C	−0.2434	0.3790	0.0291	0.098*
C11	0.08853 (14)	0.7625 (2)	0.08221 (11)	0.0529 (5)
H11	0.1406	0.7046	0.0902	0.063*
C12	0.09888 (16)	0.8958 (2)	0.11177 (13)	0.0646 (6)
H12	0.1566	0.9265	0.1397	0.078*
C13	0.02369 (17)	0.9830 (2)	0.09987 (12)	0.0551 (6)
H13	0.0289	1.0742	0.1193	0.066*
C14	−0.05893 (15)	0.9331 (2)	0.05897 (12)	0.0554 (5)
H14	−0.1115	0.9902	0.0496	0.066*
C15	−0.06440 (14)	0.7977 (2)	0.03149 (11)	0.0497 (5)
H15	−0.1216	0.7648	0.0037	0.060*

	U11	U22	U33	U12	U13	U23
Ni1	0.02844 (18)	0.03087 (18)	0.03696 (19)	0.00162 (12)	0.00618 (13)	0.00258 (13)
O1	0.0330 (6)	0.0372 (7)	0.0409 (7)	0.0014 (5)	0.0068 (5)	0.0065 (6)
N1	0.0378 (8)	0.0370 (8)	0.0406 (8)	0.0051 (7)	0.0101 (7)	0.0043 (7)
N2	0.0345 (8)	0.0331 (8)	0.0427 (8)	0.0019 (6)	0.0106 (7)	0.0009 (6)
N3	0.0373 (8)	0.0346 (8)	0.0404 (8)	−0.0003 (7)	0.0099 (7)	0.0009 (6)
C1	0.0458 (12)	0.0827 (17)	0.0591 (14)	0.0196 (12)	0.0138 (10)	0.0214 (12)
C2	0.0473 (14)	0.126 (3)	0.0819 (19)	0.0321 (16)	0.0147 (13)	0.0277 (19)
C3	0.0627 (16)	0.0872 (19)	0.0689 (17)	0.0342 (14)	−0.0003 (13)	0.0178 (14)
C4	0.0732 (17)	0.0562 (14)	0.0525 (13)	0.0089 (12)	−0.0014 (12)	0.0165 (11)
C5	0.0527 (12)	0.0444 (11)	0.0458 (11)	0.0008 (10)	0.0061 (9)	0.0033 (9)
C6	0.0409 (10)	0.0333 (9)	0.0375 (10)	0.0046 (8)	0.0039 (8)	−0.0028 (7)
C7	0.0371 (9)	0.0268 (9)	0.0354 (9)	0.0020 (7)	0.0059 (7)	−0.0035 (7)
C8	0.0410 (10)	0.0492 (11)	0.0549 (12)	0.0033 (9)	0.0201 (9)	0.0051 (9)
C9	0.0614 (15)	0.094 (2)	0.0782 (17)	0.0140 (14)	0.0386 (13)	0.0308 (15)
C10	0.0394 (11)	0.0851 (17)	0.0734 (16)	0.0077 (12)	0.0213 (11)	0.0201 (14)
C11	0.0404 (11)	0.0412 (11)	0.0693 (14)	0.0015 (9)	0.0087 (10)	−0.0077 (10)
C12	0.0497 (13)	0.0499 (13)	0.0834 (17)	−0.0085 (10)	0.0086 (12)	−0.0191 (12)
C13	0.0625 (14)	0.0358 (11)	0.0698 (15)	−0.0047 (10)	0.0261 (12)	−0.0104 (10)
C14	0.0507 (12)	0.0463 (12)	0.0691 (14)	0.0106 (10)	0.0204 (11)	−0.0057 (11)
C15	0.0387 (10)	0.0480 (11)	0.0577 (12)	0.0028 (9)	0.0104 (9)	−0.0089 (10)

Ni1—O1i	2.0175 (13)	C5—C6	1.374 (3)
Ni1—O1	2.0175 (13)	C5—H5	0.9300
Ni1—N2	2.1148 (16)	C6—C7	1.493 (2)
Ni1—N2i	2.1148 (16)	C8—C10	1.486 (3)
Ni1—N3	2.1439 (16)	C8—C9	1.493 (3)
Ni1—N3i	2.1439 (16)	C9—H9A	0.9600
O1—C7	1.275 (2)	C9—H9B	0.9600
N1—C7	1.301 (2)	C9—H9C	0.9600
N1—N2	1.404 (2)	C10—H10A	0.9600
N2—C8	1.279 (2)	C10—H10B	0.9600
N3—C15	1.325 (2)	C10—H10C	0.9600
N3—C11	1.325 (2)	C11—C12	1.368 (3)
C1—C6	1.371 (3)	C11—H11	0.9300
C1—C2	1.387 (3)	C12—C13	1.363 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.360 (4)	C13—C14	1.356 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.366 (4)	C14—C15	1.372 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.375 (3)	C15—H15	0.9300
C4—H4	0.9300
O1i—Ni1—O1	180.00 (9)	C4—C5—H5	119.6
O1i—Ni1—N2	102.19 (6)	C1—C6—C5	118.16 (19)
O1—Ni1—N2	77.81 (6)	C1—C6—C7	119.95 (18)
O1i—Ni1—N2i	77.81 (6)	C5—C6—C7	121.87 (18)
O1—Ni1—N2i	102.19 (6)	O1—C7—N1	126.67 (16)
N2—Ni1—N2i	180.00 (8)	O1—C7—C6	117.41 (16)
O1i—Ni1—N3	89.18 (6)	N1—C7—C6	115.89 (16)
O1—Ni1—N3	90.82 (6)	N2—C8—C10	120.02 (18)
N2—Ni1—N3	91.21 (6)	N2—C8—C9	123.37 (19)
N2i—Ni1—N3	88.79 (6)	C10—C8—C9	116.61 (18)
O1i—Ni1—N3i	90.82 (6)	C8—C9—H9A	109.5
O1—Ni1—N3i	89.18 (6)	C8—C9—H9B	109.5
N2—Ni1—N3i	88.79 (6)	H9A—C9—H9B	109.5
N2i—Ni1—N3i	91.21 (6)	C8—C9—H9C	109.5
N3—Ni1—N3i	180.00 (8)	H9A—C9—H9C	109.5
C7—O1—Ni1	111.61 (11)	H9B—C9—H9C	109.5
C7—N1—N2	111.65 (14)	C8—C10—H10A	109.5
C8—N2—N1	114.09 (16)	C8—C10—H10B	109.5
C8—N2—Ni1	134.88 (14)	H10A—C10—H10B	109.5
N1—N2—Ni1	110.93 (11)	C8—C10—H10C	109.5
C15—N3—C11	116.89 (17)	H10A—C10—H10C	109.5
C15—N3—Ni1	123.21 (13)	H10B—C10—H10C	109.5
C11—N3—Ni1	119.90 (13)	N3—C11—C12	123.2 (2)
C6—C1—C2	121.1 (2)	N3—C11—H11	118.4
C6—C1—H1	119.5	C12—C11—H11	118.4
C2—C1—H1	119.5	C13—C12—C11	119.3 (2)
C3—C2—C1	119.8 (3)	C13—C12—H12	120.4
C3—C2—H2	120.1	C11—C12—H12	120.4
C1—C2—H2	120.1	C14—C13—C12	118.2 (2)
C2—C3—C4	119.6 (2)	C14—C13—H13	120.9
C2—C3—H3	120.2	C12—C13—H13	120.9
C4—C3—H3	120.2	C13—C14—C15	119.5 (2)
C3—C4—C5	120.5 (2)	C13—C14—H14	120.3
C3—C4—H4	119.7	C15—C14—H14	120.3
C5—C4—H4	119.7	N3—C15—C14	123.00 (19)
C6—C5—C4	120.8 (2)	N3—C15—H15	118.5
C6—C5—H5	119.6	C14—C15—H15	118.5
N2—Ni1—O1—C7	9.82 (11)	C3—C4—C5—C6	0.8 (4)
N2i—Ni1—O1—C7	−170.18 (11)	C2—C1—C6—C5	0.7 (4)
N3—Ni1—O1—C7	100.88 (12)	C2—C1—C6—C7	−178.0 (2)
N3i—Ni1—O1—C7	−79.12 (12)	C4—C5—C6—C1	−1.2 (3)
C7—N1—N2—C8	−175.97 (16)	C4—C5—C6—C7	177.42 (19)
C7—N1—N2—Ni1	7.01 (17)	Ni1—O1—C7—N1	−10.2 (2)
O1i—Ni1—N2—C8	−5.3 (2)	Ni1—O1—C7—C6	168.00 (12)
O1—Ni1—N2—C8	174.7 (2)	N2—N1—C7—O1	1.9 (2)
N3—Ni1—N2—C8	84.12 (19)	N2—N1—C7—C6	−176.30 (14)
N3i—Ni1—N2—C8	−95.88 (19)	C1—C6—C7—O1	−0.9 (3)
O1i—Ni1—N2—N1	170.85 (10)	C5—C6—C7—O1	−179.55 (17)
O1—Ni1—N2—N1	−9.15 (10)	C1—C6—C7—N1	177.46 (19)
N3—Ni1—N2—N1	−99.72 (11)	C5—C6—C7—N1	−1.2 (3)
N3i—Ni1—N2—N1	80.28 (11)	N1—N2—C8—C10	−179.78 (19)
O1i—Ni1—N3—C15	16.25 (16)	Ni1—N2—C8—C10	−3.7 (3)
O1—Ni1—N3—C15	−163.75 (16)	N1—N2—C8—C9	0.4 (3)
N2—Ni1—N3—C15	−85.93 (16)	Ni1—N2—C8—C9	176.48 (18)
N2i—Ni1—N3—C15	94.07 (16)	C15—N3—C11—C12	1.2 (3)
O1i—Ni1—N3—C11	−163.18 (16)	Ni1—N3—C11—C12	−179.37 (19)
O1—Ni1—N3—C11	16.82 (16)	N3—C11—C12—C13	−1.0 (4)
N2—Ni1—N3—C11	94.64 (16)	C11—C12—C13—C14	0.2 (4)
N2i—Ni1—N3—C11	−85.36 (16)	C12—C13—C14—C15	0.4 (4)
C6—C1—C2—C3	0.3 (5)	C11—N3—C15—C14	−0.5 (3)
C1—C2—C3—C4	−0.7 (5)	Ni1—N3—C15—C14	−179.99 (17)
C2—C3—C4—C5	0.1 (4)	C13—C14—C15—N3	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N1ii	0.93	2.50	3.382 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N1i	0.93	2.50	3.382 (3)	157

Symmetry code: (i) .