{N'-[(E)-1-(5-Bromo-2-oxidophen-yl)ethyl-idene]-4-chloro-benzohydrazidato}pyridinenickel(II).

The title complex, [Ni(C(15)H(10)BrClN(2)O(2))(C(5)H(5)N)], displays a square-planar coordination geometry around the Ni(II) ion, formed by the tridentate hydrazone and monodentate pyridine ligands, with the N atoms in a trans arrangement about the Ni center.

Related literature

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

Experimental

Crystal data

[Ni(C15H10BrClN2O2)(C5H5N)]

M = 503.42

Monoclinic,

a = 32.430 (4) Å

b = 6.0816 (8) Å

c = 22.865 (3) Å

β = 121.422 (2)°

V = 3848.3 (9) Å3

Z = 8

Mo Kα radiation

μ = 3.25 mm−1

T = 278 K

0.18 × 0.13 × 0.10 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.581, T max = 0.723

9680 measured reflections

3401 independent reflections

2651 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.080

S = 1.02

3401 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.27 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/S160053680902234X/bh2230sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902234X/bh2230Isup2.hkl

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

[Ni(C15H10BrClNO2)(C5H5N)]	F(000) = 2016
Mr = 503.42	Dx = 1.738 Mg m−3
Monoclinic, C2/c	Melting point: 330 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 32.430 (4) Å	Cell parameters from 2958 reflections
b = 6.0816 (8) Å	θ = 2.6–25.0°
c = 22.865 (3) Å	µ = 3.25 mm−1
β = 121.422 (2)°	T = 278 K
V = 3848.3 (9) Å3	Block, green
Z = 8	0.18 × 0.13 × 0.10 mm

Siemens SMART CCD area-detector diffractometer	3401 independent reflections
Radiation source: fine-focus sealed tube	2651 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→38
Tmin = 0.581, Tmax = 0.723	k = −7→7
9680 measured reflections	l = −24→27

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0383P)2 + 2.3403P] where P = (Fo2 + 2Fc2)/3
3401 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.27 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Ni1	0.041268 (13)	0.23786 (6)	0.156018 (18)	0.04192 (13)
Br1	−0.211124 (13)	−0.09987 (7)	−0.01369 (2)	0.07519 (15)
Cl1	0.26998 (4)	−0.39055 (19)	0.14682 (6)	0.0893 (3)
O1	0.09933 (7)	0.1537 (3)	0.16792 (10)	0.0483 (5)
O2	−0.01644 (7)	0.3235 (3)	0.14192 (11)	0.0532 (5)
N1	0.05323 (9)	−0.1250 (4)	0.09609 (12)	0.0460 (6)
N2	0.01755 (9)	−0.0048 (4)	0.09955 (11)	0.0418 (6)
N3	0.07253 (9)	0.4809 (4)	0.22016 (12)	0.0449 (6)
C1	0.21951 (12)	−0.2894 (6)	0.14580 (16)	0.0572 (9)
C2	0.22207 (12)	−0.0906 (6)	0.17554 (17)	0.0647 (9)
H2	0.2510	−0.0129	0.1980	0.078*
C3	0.18122 (12)	−0.0071 (6)	0.17171 (16)	0.0578 (8)
H3	0.1827	0.1285	0.1915	0.069*
C4	0.13809 (11)	−0.1220 (5)	0.13888 (14)	0.0454 (7)
C5	0.13736 (13)	−0.3249 (5)	0.11103 (18)	0.0595 (9)
H5	0.1089	−0.4065	0.0899	0.071*
C6	0.17748 (13)	−0.4080 (6)	0.11382 (18)	0.0646 (9)
H6	0.1763	−0.5437	0.0942	0.077*
C7	0.09448 (11)	−0.0276 (5)	0.13425 (14)	0.0437 (7)
C8	−0.02649 (11)	−0.0808 (5)	0.06426 (13)	0.0417 (7)
C9	−0.03642 (12)	−0.2861 (5)	0.02193 (16)	0.0539 (8)
H9A	−0.0094	−0.3164	0.0169	0.081*
H9B	−0.0649	−0.2649	−0.0225	0.081*
H9C	−0.0413	−0.4077	0.0444	0.081*
C10	−0.06526 (10)	0.0294 (5)	0.06629 (13)	0.0415 (7)
C11	−0.05843 (11)	0.2266 (5)	0.10261 (15)	0.0456 (7)
C12	−0.09895 (12)	0.3312 (5)	0.09768 (16)	0.0545 (8)
H12	−0.0947	0.4649	0.1198	0.065*
C13	−0.14427 (12)	0.2416 (6)	0.06125 (17)	0.0564 (8)
H13	−0.1706	0.3138	0.0582	0.068*
C14	−0.15003 (11)	0.0428 (6)	0.02932 (15)	0.0516 (8)
C15	−0.11213 (11)	−0.0603 (5)	0.03060 (14)	0.0487 (7)
H15	−0.1174	−0.1926	0.0074	0.058*
C16	0.12054 (12)	0.4904 (6)	0.25973 (16)	0.0600 (9)
H16	0.1387	0.3768	0.2571	0.072*
C17	0.14431 (14)	0.6615 (6)	0.30425 (19)	0.0701 (10)
H17	0.1779	0.6628	0.3311	0.084*
C18	0.11809 (15)	0.8293 (6)	0.30861 (17)	0.0655 (10)
H18	0.1335	0.9482	0.3375	0.079*
C19	0.06898 (14)	0.8192 (5)	0.26974 (17)	0.0589 (9)
H19	0.0503	0.9294	0.2727	0.071*
C20	0.04720 (12)	0.6437 (5)	0.22580 (15)	0.0525 (8)
H20	0.0136	0.6388	0.1992	0.063*

	U11	U22	U33	U12	U13	U23
Ni1	0.0420 (2)	0.0397 (2)	0.0444 (2)	−0.00392 (17)	0.02273 (18)	−0.00596 (17)
Br1	0.0486 (2)	0.0968 (3)	0.0797 (3)	−0.0210 (2)	0.0332 (2)	−0.0084 (2)
Cl1	0.0596 (6)	0.1029 (8)	0.1085 (8)	0.0179 (6)	0.0461 (6)	−0.0134 (6)
O1	0.0456 (12)	0.0462 (12)	0.0522 (12)	−0.0061 (9)	0.0248 (10)	−0.0130 (10)
O2	0.0433 (13)	0.0501 (12)	0.0657 (13)	−0.0055 (10)	0.0281 (11)	−0.0161 (11)
N1	0.0454 (15)	0.0431 (15)	0.0514 (15)	0.0007 (12)	0.0265 (13)	−0.0048 (12)
N2	0.0445 (15)	0.0388 (13)	0.0440 (13)	−0.0011 (11)	0.0245 (12)	−0.0025 (11)
N3	0.0486 (16)	0.0436 (14)	0.0464 (14)	−0.0058 (12)	0.0275 (12)	−0.0051 (11)
C1	0.047 (2)	0.067 (2)	0.058 (2)	0.0122 (17)	0.0272 (17)	0.0007 (17)
C2	0.044 (2)	0.074 (3)	0.074 (2)	−0.0059 (17)	0.0297 (18)	−0.0151 (19)
C3	0.054 (2)	0.057 (2)	0.067 (2)	−0.0062 (17)	0.0347 (18)	−0.0163 (17)
C4	0.0454 (18)	0.0493 (19)	0.0432 (16)	0.0000 (14)	0.0242 (15)	−0.0001 (14)
C5	0.050 (2)	0.054 (2)	0.072 (2)	−0.0075 (16)	0.0299 (18)	−0.0163 (17)
C6	0.065 (2)	0.056 (2)	0.078 (2)	0.0055 (18)	0.040 (2)	−0.0129 (18)
C7	0.0457 (18)	0.0448 (17)	0.0423 (16)	0.0001 (14)	0.0241 (15)	0.0003 (14)
C8	0.0465 (18)	0.0381 (16)	0.0388 (15)	−0.0049 (13)	0.0210 (14)	0.0000 (13)
C9	0.055 (2)	0.0444 (19)	0.0595 (19)	−0.0082 (15)	0.0274 (17)	−0.0105 (15)
C10	0.0414 (17)	0.0421 (17)	0.0425 (15)	−0.0046 (13)	0.0229 (14)	0.0012 (13)
C11	0.0441 (18)	0.0476 (18)	0.0494 (17)	−0.0047 (14)	0.0274 (15)	0.0001 (14)
C12	0.053 (2)	0.0525 (19)	0.064 (2)	−0.0029 (16)	0.0350 (17)	−0.0048 (16)
C13	0.047 (2)	0.066 (2)	0.066 (2)	0.0010 (17)	0.0358 (17)	0.0043 (18)
C14	0.0421 (18)	0.063 (2)	0.0496 (18)	−0.0102 (16)	0.0239 (15)	0.0023 (16)
C15	0.0504 (19)	0.0510 (18)	0.0465 (17)	−0.0095 (15)	0.0266 (15)	−0.0020 (14)
C16	0.048 (2)	0.064 (2)	0.070 (2)	−0.0108 (17)	0.0320 (18)	−0.0193 (18)
C17	0.059 (2)	0.075 (2)	0.074 (2)	−0.025 (2)	0.033 (2)	−0.028 (2)
C18	0.085 (3)	0.059 (2)	0.062 (2)	−0.028 (2)	0.045 (2)	−0.0210 (18)
C19	0.079 (3)	0.0463 (19)	0.059 (2)	−0.0047 (18)	0.042 (2)	−0.0088 (16)
C20	0.056 (2)	0.0511 (19)	0.0510 (18)	−0.0009 (16)	0.0288 (17)	−0.0042 (15)

Ni1—O2	1.802 (2)	C8—C10	1.447 (4)
Ni1—O1	1.830 (2)	C8—C9	1.508 (4)
Ni1—N2	1.844 (2)	C9—H9A	0.9600
Ni1—N3	1.953 (2)	C9—H9B	0.9600
Br1—C14	1.901 (3)	C9—H9C	0.9600
Cl1—C1	1.737 (3)	C10—C15	1.407 (4)
O1—C7	1.306 (3)	C10—C11	1.409 (4)
O2—C11	1.317 (3)	C11—C12	1.410 (4)
N1—C7	1.298 (4)	C12—C13	1.369 (4)
N1—N2	1.405 (3)	C12—H12	0.9300
N2—C8	1.305 (4)	C13—C14	1.374 (4)
N3—C16	1.333 (4)	C13—H13	0.9300
N3—C20	1.335 (4)	C14—C15	1.366 (4)
C1—C2	1.368 (5)	C15—H15	0.9300
C1—C6	1.369 (5)	C16—C17	1.377 (4)
C2—C3	1.378 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.364 (5)
C3—C4	1.383 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.362 (5)
C4—C5	1.383 (4)	C18—H18	0.9300
C4—C7	1.478 (4)	C19—C20	1.381 (4)
C5—C6	1.366 (5)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300
O2—Ni1—O1	178.39 (9)	C8—C9—H9A	109.5
O2—Ni1—N2	95.20 (10)	C8—C9—H9B	109.5
O1—Ni1—N2	84.35 (9)	H9A—C9—H9B	109.5
O2—Ni1—N3	89.99 (10)	C8—C9—H9C	109.5
O1—Ni1—N3	90.52 (9)	H9A—C9—H9C	109.5
N2—Ni1—N3	174.43 (11)	H9B—C9—H9C	109.5
C7—O1—Ni1	110.50 (18)	C15—C10—C11	117.5 (3)
C11—O2—Ni1	126.92 (19)	C15—C10—C8	119.7 (3)
C7—N1—N2	108.4 (2)	C11—C10—C8	122.7 (3)
C8—N2—N1	116.7 (2)	O2—C11—C10	124.9 (3)
C8—N2—Ni1	129.7 (2)	O2—C11—C12	116.2 (3)
N1—N2—Ni1	113.61 (18)	C10—C11—C12	118.9 (3)
C16—N3—C20	117.5 (3)	C13—C12—C11	122.0 (3)
C16—N3—Ni1	120.5 (2)	C13—C12—H12	119.0
C20—N3—Ni1	122.0 (2)	C11—C12—H12	119.0
C2—C1—C6	121.1 (3)	C12—C13—C14	118.6 (3)
C2—C1—Cl1	119.6 (3)	C12—C13—H13	120.7
C6—C1—Cl1	119.3 (3)	C14—C13—H13	120.7
C1—C2—C3	119.1 (3)	C15—C14—C13	121.4 (3)
C1—C2—H2	120.4	C15—C14—Br1	119.0 (3)
C3—C2—H2	120.4	C13—C14—Br1	119.5 (2)
C2—C3—C4	121.0 (3)	C14—C15—C10	121.5 (3)
C2—C3—H3	119.5	C14—C15—H15	119.3
C4—C3—H3	119.5	C10—C15—H15	119.3
C3—C4—C5	118.1 (3)	N3—C16—C17	122.7 (3)
C3—C4—C7	120.1 (3)	N3—C16—H16	118.6
C5—C4—C7	121.8 (3)	C17—C16—H16	118.6
C6—C5—C4	121.4 (3)	C18—C17—C16	119.3 (4)
C6—C5—H5	119.3	C18—C17—H17	120.4
C4—C5—H5	119.3	C16—C17—H17	120.4
C5—C6—C1	119.2 (3)	C19—C18—C17	118.7 (3)
C5—C6—H6	120.4	C19—C18—H18	120.7
C1—C6—H6	120.4	C17—C18—H18	120.7
N1—C7—O1	123.1 (3)	C18—C19—C20	119.4 (3)
N1—C7—C4	118.9 (3)	C18—C19—H19	120.3
O1—C7—C4	118.0 (3)	C20—C19—H19	120.3
N2—C8—C10	120.4 (3)	N3—C20—C19	122.4 (3)
N2—C8—C9	119.3 (3)	N3—C20—H20	118.8
C10—C8—C9	120.4 (3)	C19—C20—H20	118.8
N2—Ni1—O1—C7	−2.06 (18)	N1—N2—C8—C10	178.4 (2)
N3—Ni1—O1—C7	175.76 (18)	Ni1—N2—C8—C10	−0.2 (4)
N2—Ni1—O2—C11	0.0 (2)	N1—N2—C8—C9	−1.0 (4)
N3—Ni1—O2—C11	−178.0 (2)	Ni1—N2—C8—C9	−179.5 (2)
C7—N1—N2—C8	−179.6 (2)	N2—C8—C10—C15	−177.0 (2)
C7—N1—N2—Ni1	−0.8 (3)	C9—C8—C10—C15	2.4 (4)
O2—Ni1—N2—C8	−1.3 (3)	N2—C8—C10—C11	3.4 (4)
O1—Ni1—N2—C8	−179.8 (3)	C9—C8—C10—C11	−177.3 (3)
O2—Ni1—N2—N1	−179.92 (18)	Ni1—O2—C11—C10	2.9 (4)
O1—Ni1—N2—N1	1.62 (17)	Ni1—O2—C11—C12	−177.3 (2)
O2—Ni1—N3—C16	168.9 (2)	C15—C10—C11—O2	175.5 (3)
O1—Ni1—N3—C16	−12.6 (2)	C8—C10—C11—O2	−4.9 (4)
O2—Ni1—N3—C20	−11.7 (2)	C15—C10—C11—C12	−4.3 (4)
O1—Ni1—N3—C20	166.7 (2)	C8—C10—C11—C12	175.4 (3)
C6—C1—C2—C3	−1.5 (5)	O2—C11—C12—C13	−176.7 (3)
Cl1—C1—C2—C3	177.0 (3)	C10—C11—C12—C13	3.1 (5)
C1—C2—C3—C4	0.5 (5)	C11—C12—C13—C14	0.7 (5)
C2—C3—C4—C5	1.1 (5)	C12—C13—C14—C15	−3.2 (5)
C2—C3—C4—C7	−178.9 (3)	C12—C13—C14—Br1	173.6 (2)
C3—C4—C5—C6	−1.9 (5)	C13—C14—C15—C10	1.9 (5)
C7—C4—C5—C6	178.1 (3)	Br1—C14—C15—C10	−175.0 (2)
C4—C5—C6—C1	1.0 (5)	C11—C10—C15—C14	2.0 (4)
C2—C1—C6—C5	0.7 (5)	C8—C10—C15—C14	−177.7 (3)
Cl1—C1—C6—C5	−177.8 (3)	C20—N3—C16—C17	−1.3 (5)
N2—N1—C7—O1	−1.1 (4)	Ni1—N3—C16—C17	178.0 (3)
N2—N1—C7—C4	−179.6 (2)	N3—C16—C17—C18	0.0 (5)
Ni1—O1—C7—N1	2.4 (3)	C16—C17—C18—C19	1.5 (5)
Ni1—O1—C7—C4	−179.08 (19)	C17—C18—C19—C20	−1.8 (5)
C3—C4—C7—N1	171.6 (3)	C16—N3—C20—C19	1.0 (4)
C5—C4—C7—N1	−8.4 (4)	Ni1—N3—C20—C19	−178.3 (2)
C3—C4—C7—O1	−7.0 (4)	C18—C19—C20—N3	0.5 (5)
C5—C4—C7—O1	173.0 (3)