{N′-[(E)-(5-Bromo-2-oxidophen­yl)(phenyl)­methyl­ene]-4-chloro­benzo­hydrazidato}pyridine­nickel(II)

Zheng, C.-Z.; Ji, C.-Y.; Chang, X.-L.; Kuang, X.-M.

doi:10.1107/S1600536809030943

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1060

doi:10.1107/S1600536809030943

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{N′-[(E)-(5-Bromo-2-oxidophenyl)(phenyl)methylene]-4-chlorobenzohydrazidato}pyridinenickel(II)

Chang-Zheng Zheng,^a Chang-You Ji,^a ^* Xiu-Li Chang ^b and Xin-Mou Kuang ^a

^aCollege of Environment and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China, and ^bSchool of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong, Sichuan, 643000, People's Republic of China
^*Correspondence e-mail: jichangyou789456@126.com

(Received 16 July 2009; accepted 4 August 2009; online 12 August 2009)

The asymmetric unit of title complex, [Ni(C₂₀H₁₂BrClN₂O₂)(C₅H₅N)], 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_r = 565.49
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.073
S = 1.02
4065 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030943/bh2240sup1.cif

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

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998; Ali et al., 2004) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of our work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here. The geometric features compare well with those observed in a closely related Ni^II complex including a methyl group in place of the phenyl group in the hydrazone ligand (Chang et al., 2009).

Related literature top

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 top

A DMF solution (5 ml) of N'-[(E)-(5-bromo-2-hydroxyphenyl)-(phenyl)methylene]-4-chlorobenzohydrazide (0.25 mmol, 0.108 g) was mixed with a methanol solution (5 ml) of NiCl₂.6H₂O (0.25 mmol, 0.059 g). The mixture was stirred at 298 K for 4 h. and then filtered. A red precipitate was produced after about 10 days. A pyridine amount (5 ml) was used to dissolve the precipitate at 330 K. Red block-shaped crystals of the title complex were obtained after one month (yield 30%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.

{N'-[(E)-(5-Bromo-2-oxidophenyl)(phenyl)methylene]-4- chlorobenzohydrazidato}pyridinenickel(II) top

Crystal data top

[Ni(C₂₀H₁₂BrClN₂O₂)(C₅H₅N)]	F(000) = 1136
M_r = 565.49	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0311P)² + 0.9549P] where P = (F_o² + 2F_c²)/3
4065 reflections	(Δ/σ)_max = 0.002
298 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³
0 constraints

Crystal data top

[Ni(C₂₀H₁₂BrClN₂O₂)(C₅H₅N)]	V = 2294.0 (14) Å³
M_r = 565.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.854 (3) Å	µ = 2.73 mm⁻¹
b = 21.981 (8) Å	T = 298 K
c = 10.857 (4) Å	0.21 × 0.16 × 0.12 mm
β = 102.705 (6)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4065 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3109 reflections with I > 2σ(I)
T_min = 0.586, T_max = 0.720	R_int = 0.024
11902 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.02	Δρ_max = 0.37 e Å⁻³
4065 reflections	Δρ_min = −0.40 e Å⁻³
298 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₁₂BrClN₂O₂)(C₅H₅N)]
M_r	565.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.854 (3), 21.981 (8), 10.857 (4)
β (°)	102.705 (6)
V (Å³)	2294.0 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.73
Crystal size (mm)	0.21 × 0.16 × 0.12

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.586, 0.720
No. of measured, independent and observed [I > 2σ(I)] reflections	11902, 4065, 3109
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.073, 1.02
No. of reflections	4065
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.40

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Postgraduate Foundation of Xi'an Polytechnic University (grant No. Y05–2–09).

References

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