{N'-[(E)-1-(5-Bromo-2-oxidophen-yl)ethyl-idene-κO]-4-methyl-benzohydrazidato-κN',O}(pyridine-κN)nickel(II).

The central Ni(II) atom in the title complex, [Ni(C(16)H(13)BrN(2)O(2))(C(5)H(5)N)], is in a square-planar trans-N(2)O(2) environment defined by the NO(2) donor atoms of the tridentate hydrazone ligand and the monodentate pyridine ligand. The pyridine mol-ecule forms a dihedral angle of 9.99 (11)° with the least-squares plane through the NiN(2)O(2) atoms.

Related literature

For the biological and coordination properties of aroylhydra­zones, see: Ali et al. (2004 ▶); Carcelli et al. (1995 ▶); Cheng et al. (1996 ▶); Desai et al. (2001 ▶); El-Masry et al. (2000 ▶); Singh & Dash (1988 ▶); Zheng et al. (2008 ▶).

Experimental

Crystal data

[Ni(C16H13BrN2O2)(C5H5N)]

M = 483.00

Monoclinic,

a = 32.376 (18) Å

b = 6.145 (4) Å

c = 22.752 (13) Å

β = 122.063 (8)°

V = 3836 (4) Å3

Z = 8

Mo Kα radiation

μ = 3.12 mm−1

T = 298 K

0.21 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.561, T max = 0.706

9451 measured reflections

3403 independent reflections

2415 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.03

3403 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.38 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/S1600536811029114/tk2766sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029114/tk2766Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029114/tk2766Isup3.cdx

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

[Ni(C16H13BrN2O2)(C5H5N)]	F(000) = 1952
Mr = 483.00	Dx = 1.673 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2511 reflections
a = 32.376 (18) Å	θ = 3.2–23.3°
b = 6.145 (4) Å	µ = 3.12 mm−1
c = 22.752 (13) Å	T = 298 K
β = 122.063 (8)°	Block, red
V = 3836 (4) Å3	0.21 × 0.16 × 0.12 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2415 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→38
Tmin = 0.561, Tmax = 0.706	k = −6→7
9451 measured reflections	l = −27→26

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.067P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3403 reflections	Δρmax = 0.40 e Å−3
253 parameters	Δρmin = −0.38 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	0.039679 (16)	0.25481 (7)	0.15523 (2)	0.04140 (15)
Br1	−0.214719 (15)	0.57208 (8)	−0.01235 (2)	0.07427 (19)
O1	−0.01744 (9)	0.1671 (4)	0.14220 (12)	0.0521 (6)
O2	0.09732 (8)	0.3432 (4)	0.16657 (11)	0.0461 (6)
N1	0.04942 (11)	0.6167 (5)	0.09492 (13)	0.0453 (7)
N2	0.01454 (11)	0.4946 (4)	0.09898 (13)	0.0418 (7)
N3	0.07198 (11)	0.0131 (5)	0.21834 (14)	0.0447 (7)
C1	0.25839 (16)	0.9041 (8)	0.1443 (2)	0.0827 (14)
H1A	0.2839	0.7978	0.1605	0.124*
H1B	0.2700	1.0277	0.1748	0.124*
H1C	0.2486	0.9493	0.0983	0.124*
C2	0.21573 (15)	0.8065 (7)	0.14342 (18)	0.0559 (10)
C3	0.21831 (14)	0.6056 (7)	0.17226 (19)	0.0601 (11)
H3	0.2477	0.5306	0.1947	0.072*
C4	0.17830 (14)	0.5144 (6)	0.16844 (18)	0.0534 (10)
H4	0.1810	0.3774	0.1875	0.064*
C5	0.13426 (13)	0.6209 (6)	0.13698 (17)	0.0439 (9)
C6	0.13174 (15)	0.8249 (7)	0.1090 (2)	0.0594 (10)
H6	0.1026	0.9018	0.0876	0.071*
C7	0.17177 (16)	0.9138 (7)	0.1127 (2)	0.0647 (11)
H7	0.1692	1.0510	0.0938	0.078*
C8	0.09144 (13)	0.5231 (6)	0.13248 (17)	0.0424 (9)
C9	−0.03004 (13)	0.5689 (5)	0.06399 (16)	0.0425 (8)
C10	−0.04099 (14)	0.7722 (6)	0.02212 (18)	0.0537 (10)
H10A	−0.0467	0.8895	0.0448	0.081*
H10B	−0.0695	0.7501	−0.0232	0.081*
H10C	−0.0138	0.8075	0.0179	0.081*
C11	−0.06813 (12)	0.4555 (6)	0.06651 (16)	0.0405 (8)
C12	−0.06026 (13)	0.2605 (6)	0.10355 (17)	0.0440 (9)
C13	−0.09983 (14)	0.1556 (7)	0.09951 (19)	0.0545 (10)
H13	−0.0948	0.0229	0.1220	0.065*
C14	−0.14580 (15)	0.2406 (7)	0.0637 (2)	0.0570 (10)
H14	−0.1718	0.1676	0.0614	0.068*
C15	−0.15255 (14)	0.4378 (7)	0.03092 (17)	0.0517 (10)
C16	−0.11546 (14)	0.5416 (6)	0.03128 (17)	0.0479 (9)
H16	−0.1215	0.6728	0.0077	0.058*
C17	0.04736 (15)	−0.1465 (6)	0.22590 (18)	0.0509 (9)
H17	0.0135	−0.1401	0.2007	0.061*
C18	0.07017 (17)	−0.3209 (7)	0.26964 (19)	0.0587 (11)
H18	0.0518	−0.4301	0.2733	0.070*
C19	0.11926 (17)	−0.3323 (7)	0.30699 (19)	0.0645 (12)
H19	0.1351	−0.4494	0.3364	0.077*
C20	0.14525 (17)	−0.1681 (8)	0.3008 (2)	0.0700 (12)
H20	0.1791	−0.1707	0.3264	0.084*
C21	0.12057 (15)	−0.0002 (7)	0.2563 (2)	0.0626 (11)
H21	0.1385	0.1105	0.2523	0.075*

	U11	U22	U33	U12	U13	U23
Ni1	0.0472 (3)	0.0340 (3)	0.0408 (3)	0.0066 (2)	0.0218 (2)	0.0065 (2)
Br1	0.0558 (3)	0.0908 (4)	0.0771 (3)	0.0253 (2)	0.0359 (2)	0.0117 (3)
O1	0.0495 (15)	0.0417 (15)	0.0595 (15)	0.0057 (13)	0.0252 (13)	0.0160 (12)
O2	0.0519 (15)	0.0379 (14)	0.0463 (13)	0.0045 (12)	0.0246 (12)	0.0109 (12)
N1	0.0529 (19)	0.0368 (19)	0.0454 (16)	0.0034 (15)	0.0256 (15)	0.0046 (14)
N2	0.0534 (19)	0.0298 (16)	0.0438 (16)	0.0051 (14)	0.0269 (14)	0.0033 (13)
N3	0.0533 (19)	0.0390 (19)	0.0411 (16)	0.0073 (15)	0.0246 (15)	0.0047 (13)
C1	0.069 (3)	0.094 (4)	0.083 (3)	−0.022 (3)	0.040 (3)	0.006 (3)
C2	0.058 (3)	0.059 (3)	0.046 (2)	−0.012 (2)	0.025 (2)	−0.0014 (19)
C3	0.050 (2)	0.066 (3)	0.062 (2)	0.003 (2)	0.028 (2)	0.010 (2)
C4	0.060 (3)	0.045 (2)	0.059 (2)	0.005 (2)	0.034 (2)	0.0097 (19)
C5	0.054 (2)	0.037 (2)	0.0426 (19)	0.0020 (18)	0.0266 (18)	−0.0007 (16)
C6	0.060 (3)	0.049 (2)	0.067 (3)	0.006 (2)	0.032 (2)	0.013 (2)
C7	0.075 (3)	0.046 (3)	0.075 (3)	−0.006 (2)	0.041 (2)	0.013 (2)
C8	0.054 (2)	0.034 (2)	0.0400 (19)	0.0012 (18)	0.0247 (17)	0.0000 (16)
C9	0.055 (2)	0.032 (2)	0.0396 (18)	0.0096 (18)	0.0239 (17)	0.0006 (16)
C10	0.062 (3)	0.041 (2)	0.053 (2)	0.0079 (19)	0.028 (2)	0.0117 (18)
C11	0.045 (2)	0.038 (2)	0.0388 (18)	0.0073 (17)	0.0231 (16)	−0.0006 (16)
C12	0.046 (2)	0.043 (2)	0.0408 (19)	0.0072 (18)	0.0215 (17)	0.0007 (17)
C13	0.056 (2)	0.049 (2)	0.065 (2)	0.006 (2)	0.036 (2)	0.010 (2)
C14	0.058 (3)	0.059 (3)	0.064 (2)	0.002 (2)	0.040 (2)	−0.001 (2)
C15	0.053 (2)	0.061 (3)	0.045 (2)	0.012 (2)	0.0281 (18)	−0.0001 (19)
C16	0.055 (2)	0.044 (2)	0.045 (2)	0.0145 (19)	0.0264 (18)	0.0059 (17)
C17	0.061 (2)	0.039 (2)	0.050 (2)	0.005 (2)	0.0271 (19)	0.0058 (18)
C18	0.085 (3)	0.042 (2)	0.054 (2)	0.006 (2)	0.041 (2)	0.0081 (19)
C19	0.090 (3)	0.054 (3)	0.053 (2)	0.029 (3)	0.040 (3)	0.016 (2)
C20	0.067 (3)	0.069 (3)	0.073 (3)	0.029 (3)	0.036 (2)	0.030 (2)
C21	0.059 (3)	0.063 (3)	0.069 (3)	0.016 (2)	0.036 (2)	0.024 (2)

Ni1—O1	1.794 (3)	C6—H6	0.9300
Ni1—O2	1.826 (3)	C7—H7	0.9300
Ni1—N2	1.835 (3)	C9—C11	1.444 (5)
Ni1—N3	1.941 (3)	C9—C10	1.495 (5)
Br1—C15	1.897 (4)	C10—H10A	0.9600
O1—C12	1.315 (4)	C10—H10B	0.9600
O2—C8	1.305 (4)	C10—H10C	0.9600
N1—C8	1.295 (4)	C11—C16	1.402 (5)
N1—N2	1.399 (4)	C11—C12	1.408 (5)
N2—C9	1.306 (4)	C12—C13	1.393 (5)
N3—C17	1.331 (5)	C13—C14	1.365 (5)
N3—C21	1.336 (5)	C13—H13	0.9300
C1—C2	1.496 (5)	C14—C15	1.378 (5)
C1—H1A	0.9600	C14—H14	0.9300
C1—H1B	0.9600	C15—C16	1.356 (5)
C1—H1C	0.9600	C16—H16	0.9300
C2—C7	1.376 (6)	C17—C18	1.380 (5)
C2—C3	1.380 (5)	C17—H17	0.9300
C3—C4	1.371 (5)	C18—C19	1.349 (6)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.375 (5)	C19—C20	1.368 (6)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.388 (5)	C20—C21	1.367 (5)
C5—C8	1.464 (5)	C20—H20	0.9300
C6—C7	1.368 (5)	C21—H21	0.9300
O1—Ni1—O2	178.81 (10)	N2—C9—C11	119.9 (3)
O1—Ni1—N2	95.14 (12)	N2—C9—C10	119.5 (3)
O2—Ni1—N2	84.33 (12)	C11—C9—C10	120.7 (3)
O1—Ni1—N3	89.75 (12)	C9—C10—H10A	109.5
O2—Ni1—N3	90.82 (12)	C9—C10—H10B	109.5
N2—Ni1—N3	174.87 (13)	H10A—C10—H10B	109.5
C12—O1—Ni1	127.4 (2)	C9—C10—H10C	109.5
C8—O2—Ni1	110.6 (2)	H10A—C10—H10C	109.5
C8—N1—N2	108.7 (3)	H10B—C10—H10C	109.5
C9—N2—N1	116.2 (3)	C16—C11—C12	117.3 (3)
C9—N2—Ni1	130.1 (3)	C16—C11—C9	119.5 (3)
N1—N2—Ni1	113.7 (2)	C12—C11—C9	123.2 (3)
C17—N3—C21	116.8 (3)	O1—C12—C13	116.6 (3)
C17—N3—Ni1	122.3 (3)	O1—C12—C11	124.3 (3)
C21—N3—Ni1	120.8 (3)	C13—C12—C11	119.1 (3)
C2—C1—H1A	109.5	C14—C13—C12	122.3 (4)
C2—C1—H1B	109.5	C14—C13—H13	118.8
H1A—C1—H1B	109.5	C12—C13—H13	118.8
C2—C1—H1C	109.5	C13—C14—C15	118.0 (4)
H1A—C1—H1C	109.5	C13—C14—H14	121.0
H1B—C1—H1C	109.5	C15—C14—H14	121.0
C7—C2—C3	117.1 (4)	C16—C15—C14	121.6 (4)
C7—C2—C1	120.9 (4)	C16—C15—Br1	119.4 (3)
C3—C2—C1	122.0 (4)	C14—C15—Br1	118.9 (3)
C4—C3—C2	121.3 (4)	C15—C16—C11	121.4 (4)
C4—C3—H3	119.4	C15—C16—H16	119.3
C2—C3—H3	119.4	C11—C16—H16	119.3
C3—C4—C5	121.5 (4)	N3—C17—C18	122.5 (4)
C3—C4—H4	119.3	N3—C17—H17	118.7
C5—C4—H4	119.3	C18—C17—H17	118.7
C4—C5—C6	117.4 (3)	C19—C18—C17	119.6 (4)
C4—C5—C8	121.5 (3)	C19—C18—H18	120.2
C6—C5—C8	121.0 (3)	C17—C18—H18	120.2
C7—C6—C5	120.6 (4)	C18—C19—C20	118.7 (4)
C7—C6—H6	119.7	C18—C19—H19	120.6
C5—C6—H6	119.7	C20—C19—H19	120.6
C6—C7—C2	122.1 (4)	C21—C20—C19	118.9 (4)
C6—C7—H7	119.0	C21—C20—H20	120.6
C2—C7—H7	119.0	C19—C20—H20	120.6
N1—C8—O2	122.6 (3)	N3—C21—C20	123.4 (4)
N1—C8—C5	119.2 (3)	N3—C21—H21	118.3
O2—C8—C5	118.2 (3)	C20—C21—H21	118.3
N2—Ni1—O1—C12	0.0 (3)	N1—N2—C9—C11	−178.7 (3)
N3—Ni1—O1—C12	178.4 (3)	Ni1—N2—C9—C11	−0.2 (5)
N2—Ni1—O2—C8	1.6 (2)	N1—N2—C9—C10	0.8 (4)
N3—Ni1—O2—C8	−176.7 (2)	Ni1—N2—C9—C10	179.3 (2)
C8—N1—N2—C9	179.6 (3)	N2—C9—C11—C16	177.2 (3)
C8—N1—N2—Ni1	0.9 (3)	C10—C9—C11—C16	−2.3 (5)
O1—Ni1—N2—C9	1.2 (3)	N2—C9—C11—C12	−2.2 (5)
O2—Ni1—N2—C9	−179.9 (3)	C10—C9—C11—C12	178.3 (3)
O1—Ni1—N2—N1	179.6 (2)	Ni1—O1—C12—C13	177.4 (2)
O2—Ni1—N2—N1	−1.4 (2)	Ni1—O1—C12—C11	−2.2 (5)
O1—Ni1—N3—C17	9.5 (3)	C16—C11—C12—O1	−175.9 (3)
O2—Ni1—N3—C17	−169.5 (3)	C9—C11—C12—O1	3.5 (5)
O1—Ni1—N3—C21	−170.7 (3)	C16—C11—C12—C13	4.5 (5)
O2—Ni1—N3—C21	10.3 (3)	C9—C11—C12—C13	−176.1 (3)
C7—C2—C3—C4	2.0 (6)	O1—C12—C13—C14	177.0 (3)
C1—C2—C3—C4	−177.2 (4)	C11—C12—C13—C14	−3.4 (5)
C2—C3—C4—C5	−1.3 (6)	C12—C13—C14—C15	−0.3 (6)
C3—C4—C5—C6	0.1 (5)	C13—C14—C15—C16	2.9 (5)
C3—C4—C5—C8	179.6 (3)	C13—C14—C15—Br1	−174.5 (3)
C4—C5—C6—C7	0.4 (5)	C14—C15—C16—C11	−1.6 (5)
C8—C5—C6—C7	−179.2 (3)	Br1—C15—C16—C11	175.8 (2)
C5—C6—C7—C2	0.4 (6)	C12—C11—C16—C15	−2.1 (5)
C3—C2—C7—C6	−1.5 (6)	C9—C11—C16—C15	178.4 (3)
C1—C2—C7—C6	177.7 (4)	C21—N3—C17—C18	−1.2 (5)
N2—N1—C8—O2	0.6 (4)	Ni1—N3—C17—C18	178.6 (3)
N2—N1—C8—C5	−179.8 (3)	N3—C17—C18—C19	0.5 (6)
Ni1—O2—C8—N1	−1.7 (4)	C17—C18—C19—C20	0.6 (6)
Ni1—O2—C8—C5	178.6 (2)	C18—C19—C20—C21	−0.9 (6)
C4—C5—C8—N1	−171.3 (3)	C17—N3—C21—C20	0.8 (6)
C6—C5—C8—N1	8.2 (5)	Ni1—N3—C21—C20	−179.0 (3)
C4—C5—C8—O2	8.3 (5)	C19—C20—C21—N3	0.2 (7)
C6—C5—C8—O2	−172.2 (3)

Table 1

Selected bond lengths (Å)

Ni1—O1	1.794 (3)
Ni1—O2	1.826 (3)
Ni1—N2	1.835 (3)
Ni1—N3	1.941 (3)