{N'-[(E)-(5-Bromo-2-oxidophen-yl)(phenyl)-methyl-ene]-4-chloro-benzo-hydrazidato}pyridine-nickel(II).

The asymmetric unit of title complex, [Ni(C(20)H(12)BrClN(2)O(2))(C(5)H(5)N)], contains one complex with the central Ni atom in a slightly distorted square-planar environment, formed by the tridentate hydrazone and the monodentate pyridine ligands, with N atoms in a trans arrangement about the Ni atom.

Related literature

For the coordination properties of aroylhydrazones, see: Ali et al. (2004 ▶); Carcelli et al. (1995 ▶); Salem (1998 ▶); Singh et al. (1982 ▶); Chang et al. (2009 ▶).

Experimental

Crystal data

[Ni(C20H12BrClN2O2)(C5H5N)]

M = 565.49

Monoclinic,

a = 9.854 (3) Å

b = 21.981 (8) Å

c = 10.857 (4) Å

β = 102.705 (6)°

V = 2294.0 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.73 mm−1

T = 298 K

0.21 × 0.16 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.586, T max = 0.720

11902 measured reflections

4065 independent reflections

3109 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.073

S = 1.02

4065 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 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 datablocks I, global. DOI: 10.1107/S1600536809030943/bh2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030943/bh2240Isup2.hkl

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

[Ni(C20H12BrClN2O2)(C5H5N)]	F(000) = 1136
Mr = 565.49	Dx = 1.637 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3944 reflections
a = 9.854 (3) Å	θ = 2.3–25.5°
b = 21.981 (8) Å	µ = 2.73 mm−1
c = 10.857 (4) Å	T = 298 K
β = 102.705 (6)°	Block, red
V = 2294.0 (14) Å3	0.21 × 0.16 × 0.12 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	4065 independent reflections
Radiation source: fine-focus sealed tube	3109 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.586, Tmax = 0.720	k = −26→25
11902 measured reflections	l = −12→5

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0311P)2 + 0.9549P] where P = (Fo2 + 2Fc2)/3
4065 reflections	(Δ/σ)max = 0.002
298 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.40 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Ni1	0.26454 (3)	0.532600 (15)	1.11149 (3)	0.04069 (11)
Br1	−0.09024 (4)	0.248039 (14)	0.90729 (4)	0.07783 (14)
Cl1	0.75673 (10)	0.74454 (4)	0.73128 (10)	0.0848 (3)
O1	0.14617 (18)	0.47902 (8)	1.15713 (16)	0.0472 (5)
O2	0.37690 (18)	0.59030 (8)	1.06354 (16)	0.0458 (4)
N1	0.2572 (2)	0.50057 (9)	0.95458 (19)	0.0383 (5)
N2	0.3321 (2)	0.53375 (10)	0.8816 (2)	0.0430 (5)
N3	0.2890 (2)	0.56951 (10)	1.2752 (2)	0.0448 (5)
C1	0.0919 (3)	0.43111 (12)	1.0924 (2)	0.0419 (6)
C2	0.1125 (2)	0.41494 (11)	0.9716 (2)	0.0374 (6)
C3	0.0546 (3)	0.35969 (11)	0.9185 (3)	0.0431 (6)
H3	0.0689	0.3476	0.8403	0.052*
C4	−0.0217 (3)	0.32383 (12)	0.9796 (3)	0.0492 (7)
C5	−0.0490 (3)	0.34103 (13)	1.0941 (3)	0.0545 (7)
H5	−0.1042	0.3169	1.1335	0.065*
C6	0.0061 (3)	0.39382 (13)	1.1481 (3)	0.0521 (7)
H6	−0.0135	0.4057	1.2246	0.062*
C7	0.1913 (2)	0.45224 (11)	0.9028 (2)	0.0367 (6)
C8	0.1938 (2)	0.43598 (11)	0.7696 (2)	0.0366 (6)
C9	0.0738 (3)	0.44230 (13)	0.6775 (3)	0.0510 (7)
H9	−0.0051	0.4591	0.6978	0.061*
C10	0.0701 (3)	0.42394 (16)	0.5556 (3)	0.0608 (8)
H10	−0.0112	0.4284	0.4938	0.073*
C11	0.1853 (3)	0.39918 (14)	0.5251 (3)	0.0595 (8)
H11	0.1819	0.3857	0.4433	0.071*
C12	0.3056 (3)	0.39419 (14)	0.6150 (3)	0.0571 (8)
H12	0.3848	0.3783	0.5935	0.069*
C13	0.3110 (3)	0.41244 (12)	0.7371 (3)	0.0481 (7)
H13	0.3935	0.4089	0.7977	0.058*
C14	0.3916 (3)	0.57897 (12)	0.9492 (2)	0.0419 (6)
C15	0.4824 (3)	0.62008 (12)	0.8963 (2)	0.0428 (6)
C16	0.5334 (3)	0.60263 (13)	0.7936 (3)	0.0496 (7)
H16	0.5109	0.5645	0.7579	0.060*
C17	0.6169 (3)	0.64078 (14)	0.7431 (3)	0.0574 (8)
H17	0.6502	0.6287	0.6731	0.069*
C18	0.6507 (3)	0.69658 (13)	0.7959 (3)	0.0551 (8)
C19	0.6050 (4)	0.71440 (15)	0.8996 (3)	0.0739 (10)
H19	0.6304	0.7522	0.9361	0.089*
C20	0.5210 (4)	0.67624 (13)	0.9501 (3)	0.0672 (9)
H20	0.4898	0.6883	1.0212	0.081*
C21	0.2964 (3)	0.53641 (14)	1.3794 (3)	0.0527 (7)
H21	0.2938	0.4942	1.3723	0.063*
C22	0.3077 (3)	0.56172 (16)	1.4965 (3)	0.0616 (8)
H22	0.3138	0.5372	1.5674	0.074*
C23	0.3100 (3)	0.62345 (17)	1.5074 (3)	0.0681 (9)
H23	0.3158	0.6418	1.5856	0.082*
C24	0.3034 (3)	0.65820 (15)	1.4015 (3)	0.0662 (9)
H24	0.3050	0.7004	1.4070	0.079*
C25	0.2946 (3)	0.63000 (13)	1.2870 (3)	0.0558 (8)
H25	0.2923	0.6537	1.2156	0.067*

	U11	U22	U33	U12	U13	U23
Ni1	0.0429 (2)	0.0438 (2)	0.03664 (19)	−0.00025 (15)	0.01135 (14)	−0.00238 (15)
Br1	0.1043 (3)	0.0495 (2)	0.0882 (3)	−0.02548 (18)	0.0396 (2)	−0.00483 (17)
Cl1	0.0865 (6)	0.0756 (6)	0.0996 (7)	−0.0186 (5)	0.0359 (5)	0.0262 (5)
O1	0.0524 (11)	0.0530 (11)	0.0399 (10)	−0.0067 (9)	0.0185 (9)	−0.0045 (9)
O2	0.0524 (11)	0.0451 (10)	0.0413 (10)	−0.0079 (9)	0.0134 (8)	−0.0051 (8)
N1	0.0394 (12)	0.0400 (12)	0.0371 (12)	−0.0016 (10)	0.0118 (9)	0.0003 (10)
N2	0.0455 (12)	0.0440 (12)	0.0419 (12)	−0.0066 (11)	0.0147 (10)	−0.0010 (11)
N3	0.0419 (13)	0.0511 (14)	0.0429 (14)	0.0027 (10)	0.0126 (10)	−0.0044 (11)
C1	0.0404 (15)	0.0457 (15)	0.0405 (16)	0.0022 (12)	0.0107 (12)	0.0083 (13)
C2	0.0354 (13)	0.0393 (14)	0.0386 (15)	0.0033 (11)	0.0101 (11)	0.0051 (12)
C3	0.0475 (16)	0.0414 (15)	0.0426 (15)	0.0019 (12)	0.0143 (12)	0.0040 (12)
C4	0.0529 (17)	0.0413 (15)	0.0549 (18)	−0.0066 (13)	0.0149 (14)	0.0048 (13)
C5	0.0594 (18)	0.0567 (18)	0.0509 (18)	−0.0104 (15)	0.0194 (15)	0.0132 (15)
C6	0.0548 (18)	0.0645 (19)	0.0399 (16)	−0.0045 (15)	0.0168 (13)	0.0040 (14)
C7	0.0348 (13)	0.0391 (14)	0.0374 (14)	0.0037 (11)	0.0106 (11)	0.0023 (11)
C8	0.0389 (14)	0.0355 (13)	0.0373 (14)	−0.0051 (11)	0.0127 (12)	−0.0009 (11)
C9	0.0389 (16)	0.0704 (19)	0.0456 (17)	0.0044 (14)	0.0131 (13)	−0.0035 (14)
C10	0.0491 (18)	0.094 (2)	0.0395 (17)	−0.0009 (16)	0.0092 (14)	−0.0041 (16)
C11	0.063 (2)	0.076 (2)	0.0442 (17)	−0.0075 (17)	0.0231 (15)	−0.0117 (15)
C12	0.0510 (18)	0.067 (2)	0.0596 (19)	0.0080 (15)	0.0262 (16)	−0.0087 (16)
C13	0.0399 (15)	0.0561 (17)	0.0493 (17)	0.0040 (13)	0.0122 (13)	−0.0042 (14)
C14	0.0420 (15)	0.0422 (15)	0.0422 (16)	0.0016 (12)	0.0106 (12)	0.0002 (13)
C15	0.0435 (16)	0.0406 (15)	0.0433 (16)	0.0001 (12)	0.0076 (12)	0.0027 (12)
C16	0.0477 (16)	0.0490 (16)	0.0542 (18)	−0.0042 (13)	0.0157 (14)	−0.0065 (14)
C17	0.0555 (19)	0.064 (2)	0.0592 (19)	−0.0024 (15)	0.0262 (15)	0.0005 (16)
C18	0.0520 (17)	0.0527 (18)	0.061 (2)	−0.0030 (14)	0.0141 (15)	0.0148 (15)
C19	0.106 (3)	0.0446 (18)	0.077 (2)	−0.0216 (18)	0.033 (2)	−0.0047 (17)
C20	0.098 (3)	0.0495 (18)	0.064 (2)	−0.0193 (17)	0.0373 (19)	−0.0090 (16)
C21	0.0522 (17)	0.0596 (18)	0.0451 (17)	0.0029 (15)	0.0081 (13)	−0.0012 (15)
C22	0.062 (2)	0.079 (2)	0.0418 (18)	0.0070 (17)	0.0070 (15)	−0.0043 (16)
C23	0.064 (2)	0.090 (3)	0.048 (2)	0.0167 (18)	0.0085 (16)	−0.0215 (19)
C24	0.071 (2)	0.0582 (19)	0.070 (2)	0.0103 (17)	0.0174 (18)	−0.0202 (18)
C25	0.0603 (19)	0.0534 (19)	0.0555 (19)	0.0071 (14)	0.0167 (15)	−0.0066 (15)

Ni1—O1	1.8020 (18)	C10—C11	1.364 (4)
Ni1—N1	1.830 (2)	C10—H10	0.9300
Ni1—O2	1.8327 (18)	C11—C12	1.364 (4)
Ni1—N3	1.920 (2)	C11—H11	0.9300
Br1—C4	1.901 (3)	C12—C13	1.374 (4)
Cl1—C18	1.737 (3)	C12—H12	0.9300
O1—C1	1.313 (3)	C13—H13	0.9300
O2—C14	1.305 (3)	C14—C15	1.474 (4)
N1—C7	1.306 (3)	C15—C16	1.375 (4)
N1—N2	1.400 (3)	C15—C20	1.383 (4)
N2—C14	1.297 (3)	C16—C17	1.371 (4)
N3—C21	1.333 (3)	C16—H16	0.9300
N3—C25	1.336 (4)	C17—C18	1.364 (4)
C1—C6	1.406 (4)	C17—H17	0.9300
C1—C2	1.416 (3)	C18—C19	1.359 (4)
C2—C3	1.410 (3)	C19—C20	1.375 (4)
C2—C7	1.446 (3)	C19—H19	0.9300
C3—C4	1.358 (4)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.370 (4)
C4—C5	1.381 (4)	C21—H21	0.9300
C5—C6	1.359 (4)	C22—C23	1.362 (4)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.370 (4)
C7—C8	1.494 (3)	C23—H23	0.9300
C8—C9	1.378 (4)	C24—C25	1.375 (4)
C8—C13	1.381 (3)	C24—H24	0.9300
C9—C10	1.377 (4)	C25—H25	0.9300
C9—H9	0.9300
O1—Ni1—N1	96.26 (9)	C10—C11—C12	119.9 (3)
O1—Ni1—O2	176.73 (8)	C10—C11—H11	120.1
N1—Ni1—O2	84.52 (8)	C12—C11—H11	120.1
O1—Ni1—N3	88.78 (9)	C11—C12—C13	120.6 (3)
N1—Ni1—N3	174.55 (9)	C11—C12—H12	119.7
O2—Ni1—N3	90.56 (9)	C13—C12—H12	119.7
C1—O1—Ni1	126.12 (16)	C12—C13—C8	119.9 (3)
C14—O2—Ni1	109.80 (16)	C12—C13—H13	120.0
C7—N1—N2	117.0 (2)	C8—C13—H13	120.0
C7—N1—Ni1	128.91 (17)	N2—C14—O2	123.6 (2)
N2—N1—Ni1	114.09 (15)	N2—C14—C15	119.2 (2)
C14—N2—N1	108.0 (2)	O2—C14—C15	117.2 (2)
C21—N3—C25	118.0 (2)	C16—C15—C20	118.4 (3)
C21—N3—Ni1	121.80 (19)	C16—C15—C14	120.4 (2)
C25—N3—Ni1	120.2 (2)	C20—C15—C14	121.1 (3)
O1—C1—C6	116.8 (2)	C17—C16—C15	120.8 (3)
O1—C1—C2	124.9 (2)	C17—C16—H16	119.6
C6—C1—C2	118.3 (2)	C15—C16—H16	119.6
C3—C2—C1	117.9 (2)	C18—C17—C16	119.6 (3)
C3—C2—C7	119.5 (2)	C18—C17—H17	120.2
C1—C2—C7	122.6 (2)	C16—C17—H17	120.2
C4—C3—C2	121.2 (2)	C19—C18—C17	120.8 (3)
C4—C3—H3	119.4	C19—C18—Cl1	119.9 (2)
C2—C3—H3	119.4	C17—C18—Cl1	119.3 (2)
C3—C4—C5	121.2 (3)	C18—C19—C20	119.6 (3)
C3—C4—Br1	119.4 (2)	C18—C19—H19	120.2
C5—C4—Br1	119.3 (2)	C20—C19—H19	120.2
C6—C5—C4	118.9 (3)	C19—C20—C15	120.7 (3)
C6—C5—H5	120.5	C19—C20—H20	119.7
C4—C5—H5	120.5	C15—C20—H20	119.7
C5—C6—C1	122.2 (3)	N3—C21—C22	122.9 (3)
C5—C6—H6	118.9	N3—C21—H21	118.5
C1—C6—H6	118.9	C22—C21—H21	118.5
N1—C7—C2	120.8 (2)	C23—C22—C21	118.8 (3)
N1—C7—C8	119.9 (2)	C23—C22—H22	120.6
C2—C7—C8	119.3 (2)	C21—C22—H22	120.6
C9—C8—C13	119.0 (2)	C22—C23—C24	119.1 (3)
C9—C8—C7	118.9 (2)	C22—C23—H23	120.4
C13—C8—C7	122.0 (2)	C24—C23—H23	120.4
C10—C9—C8	120.4 (3)	C23—C24—C25	119.3 (3)
C10—C9—H9	119.8	C23—C24—H24	120.3
C8—C9—H9	119.8	C25—C24—H24	120.3
C11—C10—C9	120.2 (3)	N3—C25—C24	121.9 (3)
C11—C10—H10	119.9	N3—C25—H25	119.1
C9—C10—H10	119.9	C24—C25—H25	119.1
N1—Ni1—O1—C1	5.7 (2)	C2—C7—C8—C9	68.7 (3)
N3—Ni1—O1—C1	−172.2 (2)	N1—C7—C8—C13	73.1 (3)
N1—Ni1—O2—C14	0.11 (17)	C2—C7—C8—C13	−108.6 (3)
N3—Ni1—O2—C14	177.75 (17)	C13—C8—C9—C10	1.6 (4)
O1—Ni1—N1—C7	−3.5 (2)	C7—C8—C9—C10	−175.7 (3)
O2—Ni1—N1—C7	179.7 (2)	C8—C9—C10—C11	0.2 (5)
O1—Ni1—N1—N2	175.72 (16)	C9—C10—C11—C12	−1.9 (5)
O2—Ni1—N1—N2	−1.09 (16)	C10—C11—C12—C13	1.7 (5)
C7—N1—N2—C14	−178.9 (2)	C11—C12—C13—C8	0.1 (4)
Ni1—N1—N2—C14	1.8 (2)	C9—C8—C13—C12	−1.8 (4)
O1—Ni1—N3—C21	39.0 (2)	C7—C8—C13—C12	175.5 (2)
O2—Ni1—N3—C21	−144.2 (2)	N1—N2—C14—O2	−1.9 (3)
O1—Ni1—N3—C25	−138.8 (2)	N1—N2—C14—C15	177.5 (2)
O2—Ni1—N3—C25	38.0 (2)	Ni1—O2—C14—N2	1.1 (3)
Ni1—O1—C1—C6	177.42 (18)	Ni1—O2—C14—C15	−178.35 (17)
Ni1—O1—C1—C2	−3.2 (4)	N2—C14—C15—C16	−17.2 (4)
O1—C1—C2—C3	175.7 (2)	O2—C14—C15—C16	162.2 (2)
C6—C1—C2—C3	−4.9 (4)	N2—C14—C15—C20	164.3 (3)
O1—C1—C2—C7	−3.5 (4)	O2—C14—C15—C20	−16.3 (4)
C6—C1—C2—C7	175.9 (2)	C20—C15—C16—C17	−2.1 (4)
C1—C2—C3—C4	1.8 (4)	C14—C15—C16—C17	179.4 (3)
C7—C2—C3—C4	−179.1 (2)	C15—C16—C17—C18	0.5 (5)
C2—C3—C4—C5	2.0 (4)	C16—C17—C18—C19	1.3 (5)
C2—C3—C4—Br1	−177.16 (19)	C16—C17—C18—Cl1	179.9 (2)
C3—C4—C5—C6	−2.4 (4)	C17—C18—C19—C20	−1.5 (5)
Br1—C4—C5—C6	176.8 (2)	Cl1—C18—C19—C20	179.9 (3)
C4—C5—C6—C1	−1.0 (4)	C18—C19—C20—C15	−0.1 (5)
O1—C1—C6—C5	−175.9 (2)	C16—C15—C20—C19	1.9 (5)
C2—C1—C6—C5	4.7 (4)	C14—C15—C20—C19	−179.6 (3)
N2—N1—C7—C2	179.4 (2)	C25—N3—C21—C22	0.8 (4)
Ni1—N1—C7—C2	−1.4 (3)	Ni1—N3—C21—C22	−177.1 (2)
N2—N1—C7—C8	−2.3 (3)	N3—C21—C22—C23	0.8 (5)
Ni1—N1—C7—C8	176.90 (17)	C21—C22—C23—C24	−1.2 (5)
C3—C2—C7—N1	−173.4 (2)	C22—C23—C24—C25	0.1 (5)
C1—C2—C7—N1	5.7 (4)	C21—N3—C25—C24	−1.9 (4)
C3—C2—C7—C8	8.3 (3)	Ni1—N3—C25—C24	176.0 (2)
C1—C2—C7—C8	−172.6 (2)	C23—C24—C25—N3	1.5 (5)
N1—C7—C8—C9	−109.7 (3)