catena-Poly[[tripyridine­nickel(II)]-μ-5-bromo­isophthalato]

Liu, L.

doi:10.1107/S1600536808018916

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m974

doi:10.1107/S1600536808018916

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catena-Poly[[tripyridinenickel(II)]-μ-5-bromoisophthalato]

Lijun Liu ^a ^*

^aDepartment of Chemistry, Liaocheng University, Liaocheng, Shandong 252059, People's Republic of China
^*Correspondence e-mail: liulijun@lcu.edu.cn

(Received 10 June 2008; accepted 23 June 2008; online 28 June 2008)

The title compound, [Ni(C₈H₃BrO₄)(C₅H₅N)₃], is the first structurally characterized complex with a transition metal coordinated by a 5-bromoisophthalate anion. The Ni^II ion is coordinated by three O atoms from the carboxylate groups and three N atoms from three pyridine ligands in a distorted octahedral coordination geometry. The 5-bromoisophthalate anion is planar within 0.057 (2) Å. The two carboxylate groups of the ligand coordinate the Ni^II ions in a chelating and monodentate mode, linking the metal atoms into infinite chains along the [010] direction. These chains are stacked together via strong π–π interactions between the pyridine rings [centroid–centroid distance 3.601 (4) Å], forming a three-dimensional motif.

Related literature

For related literature, see: Therrien et al. (2005 ).

Experimental

Crystal data

[Ni(C₈H₃BrO₄)(C₅H₅N)₃]
M_r = 539.02
Monoclinic, C 2/c
a = 19.6621 (6) Å
b = 16.0190 (6) Å
c = 14.8755 (5) Å
β = 111.504 (2)°
V = 4359.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 296 (2) K
0.22 × 0.20 × 0.08 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.582, T_max = 0.809
22727 measured reflections
5402 independent reflections
4195 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.096
S = 1.05
5402 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Br1—C5	1.899 (2)
Ni1—N2	2.1439 (19)
Ni1—O2	2.1655 (17)
Ni1—O1	2.2024 (17)

N2—Ni1—O2	152.98 (7)
N2—Ni1—O1	92.78 (7)
O2—Ni1—O1	60.20 (6)
N2—Ni1—N1	90.11 (7)
O2—Ni1—N1	90.48 (7)
O1—Ni1—N1	90.02 (7)
N2—Ni1—N3	91.78 (7)
O2—Ni1—N3	88.13 (7)
O1—Ni1—N3	90.54 (7)
N1—Ni1—N3	178.00 (7)

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536808018916/fj2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018916/fj2127Isup2.hkl

checkCIF report

Comment top

The 5-bromoisophthalic acid ligand (H₂BIPA) was hitherto reported in its molecular form in the cystal structure of its cocrystal complex (Therrien et al., 2005). This paper provides the fist example of its structurally characterized complex with a transition metal; the ligand in this complex is twice deprotonated.

The asymmetric unit of Ni(BIPA)(C₅H₅N)₃ occupies a general position in the unit cell; the Ni atom is coordinated by four O atoms from the carboxylicate groups and three N atoms from the pyridine ligands (Ni1—N2 2.143 (2), Ni1—O2 2.165 (2), Ni1—O1 2.202 (2), Ni1—N1 2.204 (2), Ni1—N3 2.204 (2) and Ni1—O3 1.996 (2) Å) (Fig. 1). The BIPA ligand has essentially planar conformation, the maximum deviation of the O3 atom from its mean plane being 0.057 (2) Å. The geometry of the ligand is similar to the one observed in Therrien et al., (2005).

No guest molecule or Hydrogen bond was detected in the structure; The two carboxylate groups of the ligand coordinated with the Ni(II) in monodentate and chelated mode, respectively, linking the Ni(II) ion into an infinte chain along the (010) direction. The chains are stacked together via the strong π-π interactions between the pyridine rings to form a three-dimensional motif.(Fig. 2).

Related literature top

For related literature, see: Therrien et al. (2005).

Experimental top

NiCl₂.4H₂O (0.5 mmol, 101 mg) and 5-bromoisophthalic acid (0.5 mmol, 123 mg) were added to 30 ml of distilled water. After stirring for 15 min at room temperature, the pH value was adjusted to 6 by few drops of pyridine, and clear solution was allowed to evaporate in the ventilating cabinet. Light green plate crystals of the title compound were obtained after 4 days, in yields of 35%. The crystals were filtered, washed by cold EtOH and dried in the air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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. Molecular structure showing 50% probability displacement ellipsoids. The unlabeled atoms are derived from the reference atoms by means of the (1.5 - x, -1/2 + y, 1.5 - z) symmetry transformation..
	Fig. 2. Packing diagram viewed down the b axis,

catena-Poly[[tripyridinenickel(II)]-µ-5-bromoisophthalato] top

Crystal data top

[Ni(C₈H₃BrO₄)(C₅H₅N)₃]	F(000) = 2176
M_r = 539.02	D_x = 1.643 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9035 reflections
a = 19.6621 (6) Å	θ = 2.7–28.7°
b = 16.0190 (6) Å	µ = 2.76 mm⁻¹
c = 14.8755 (5) Å	T = 296 K
β = 111.504 (2)°	Plate, green
V = 4359.2 (3) Å³	0.22 × 0.20 × 0.08 mm
Z = 8

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	5402 independent reflections
Radiation source: fine-focus sealed tube	4195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
T_min = 0.582, T_max = 0.809	k = −21→21
22727 measured reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0529P)² + 2.0236P] where P = (F_o² + 2F_c²)/3
5402 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Ni(C₈H₃BrO₄)(C₅H₅N)₃]	V = 4359.2 (3) Å³
M_r = 539.02	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.6621 (6) Å	µ = 2.76 mm⁻¹
b = 16.0190 (6) Å	T = 296 K
c = 14.8755 (5) Å	0.22 × 0.20 × 0.08 mm
β = 111.504 (2)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	5402 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4195 reflections with I > 2σ(I)
T_min = 0.582, T_max = 0.809	R_int = 0.034
22727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	Δρ_max = 0.65 e Å⁻³
5402 reflections	Δρ_min = −0.34 e Å⁻³
289 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Br1	1.104271 (13)	1.027190 (17)	0.93289 (2)	0.04600 (10)
Ni1	0.833627 (16)	0.667412 (18)	0.78863 (2)	0.03305 (10)
O1	0.92550 (9)	0.75627 (10)	0.83248 (13)	0.0385 (4)
N1	0.83251 (11)	0.66980 (12)	0.93619 (15)	0.0352 (4)
C1	0.87970 (13)	0.81533 (14)	0.80832 (16)	0.0313 (5)
O2	0.81214 (9)	0.80030 (10)	0.77426 (13)	0.0386 (4)
N2	0.90493 (11)	0.56123 (12)	0.82571 (14)	0.0333 (4)
C2	0.82483 (13)	1.12204 (14)	0.78305 (16)	0.0314 (5)
O3	0.75769 (9)	1.09924 (11)	0.75262 (12)	0.0396 (4)
N3	0.83124 (11)	0.66766 (12)	0.63935 (15)	0.0351 (4)
C3	0.87912 (12)	1.05099 (14)	0.81091 (16)	0.0282 (4)
O4	0.84705 (11)	1.19426 (11)	0.79268 (15)	0.0487 (5)
C4	0.95349 (12)	1.06846 (14)	0.85107 (16)	0.0309 (5)
H4	0.9698	1.1234	0.8609	0.037*
C5	1.00279 (12)	1.00317 (15)	0.87614 (16)	0.0311 (5)
C6	0.98030 (12)	0.92097 (14)	0.86223 (17)	0.0318 (5)
H6	1.0143	0.8778	0.8796	0.038*
C7	0.90594 (12)	0.90378 (13)	0.82181 (16)	0.0291 (5)
C8	0.85606 (13)	0.96895 (14)	0.79651 (16)	0.0298 (5)
H8	0.8063	0.9572	0.7694	0.036*
C9	0.85644 (15)	0.73386 (16)	0.99719 (19)	0.0425 (6)
H9	0.8809	0.7770	0.9799	0.051*
C10	0.79950 (15)	0.60768 (16)	0.9655 (2)	0.0426 (6)
H10	0.7834	0.5614	0.9256	0.051*
C11	0.84689 (16)	0.73964 (17)	1.0846 (2)	0.0467 (6)
H11	0.8646	0.7855	1.1247	0.056*
C12	0.78831 (15)	0.60906 (19)	1.0510 (2)	0.0481 (7)
H12	0.7655	0.5644	1.0684	0.058*
C13	0.81117 (16)	0.67711 (18)	1.1112 (2)	0.0479 (7)
H13	0.8025	0.6803	1.1685	0.058*
C14	0.97593 (15)	0.57400 (17)	0.8668 (2)	0.0509 (7)
H14	0.9924	0.6288	0.8794	0.061*
C15	0.88262 (15)	0.48241 (16)	0.8088 (2)	0.0452 (6)
H15	0.8328	0.4721	0.7791	0.054*
C16	1.02719 (16)	0.5108 (2)	0.8921 (3)	0.0647 (9)
H16	1.0768	0.5228	0.9200	0.078*
C17	0.92961 (17)	0.41524 (17)	0.8331 (2)	0.0520 (7)
H17	0.9118	0.3609	0.8213	0.062*
C18	1.00334 (17)	0.43030 (19)	0.8752 (2)	0.0569 (8)
H18	1.0365	0.3863	0.8918	0.068*
C19	0.77634 (15)	0.63156 (16)	0.56745 (19)	0.0419 (6)
H19	0.7427	0.6000	0.5835	0.050*
C20	0.87919 (15)	0.71115 (17)	0.6137 (2)	0.0434 (6)
H20	0.9185	0.7359	0.6621	0.052*
C21	0.76665 (16)	0.63834 (18)	0.4714 (2)	0.0478 (7)
H21	0.7276	0.6118	0.4244	0.057*
C22	0.87340 (17)	0.72126 (19)	0.5186 (2)	0.0504 (7)
H22	0.9080	0.7522	0.5040	0.061*
C23	0.81539 (16)	0.68473 (18)	0.4458 (2)	0.0488 (7)
H23	0.8096	0.6914	0.3813	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02529 (13)	0.04761 (17)	0.05865 (18)	−0.00510 (11)	0.00777 (11)	−0.00334 (12)
Ni1	0.02778 (16)	0.02420 (15)	0.04311 (19)	−0.00138 (11)	0.00821 (13)	−0.00097 (12)
O1	0.0380 (9)	0.0225 (8)	0.0521 (10)	0.0005 (7)	0.0130 (8)	−0.0004 (7)
N1	0.0341 (11)	0.0288 (10)	0.0404 (11)	0.0037 (8)	0.0107 (9)	−0.0003 (8)
C1	0.0334 (12)	0.0258 (11)	0.0337 (12)	−0.0037 (9)	0.0113 (10)	0.0000 (9)
O2	0.0331 (9)	0.0283 (8)	0.0503 (10)	−0.0051 (7)	0.0103 (8)	−0.0015 (7)
N2	0.0304 (10)	0.0277 (9)	0.0387 (11)	0.0032 (8)	0.0091 (8)	0.0007 (8)
C2	0.0350 (12)	0.0280 (11)	0.0306 (11)	0.0075 (9)	0.0114 (10)	0.0030 (9)
O3	0.0276 (9)	0.0359 (9)	0.0488 (10)	0.0089 (7)	0.0063 (7)	0.0004 (8)
N3	0.0340 (11)	0.0285 (10)	0.0404 (11)	0.0035 (8)	0.0109 (9)	0.0002 (8)
C3	0.0281 (11)	0.0254 (10)	0.0312 (11)	0.0016 (8)	0.0108 (9)	0.0001 (9)
O4	0.0485 (11)	0.0266 (9)	0.0697 (13)	0.0064 (8)	0.0203 (10)	0.0038 (8)
C4	0.0316 (12)	0.0230 (10)	0.0371 (12)	−0.0023 (9)	0.0116 (10)	−0.0016 (9)
C5	0.0215 (10)	0.0338 (11)	0.0343 (12)	−0.0012 (9)	0.0061 (9)	−0.0003 (9)
C6	0.0267 (11)	0.0272 (11)	0.0384 (12)	0.0050 (9)	0.0084 (9)	0.0016 (9)
C7	0.0300 (11)	0.0242 (10)	0.0324 (11)	0.0006 (9)	0.0107 (9)	0.0006 (9)
C8	0.0257 (11)	0.0272 (11)	0.0350 (12)	−0.0004 (9)	0.0094 (9)	0.0011 (9)
C9	0.0464 (15)	0.0333 (13)	0.0454 (15)	0.0002 (11)	0.0140 (12)	−0.0009 (11)
C10	0.0405 (14)	0.0361 (13)	0.0466 (15)	−0.0023 (11)	0.0105 (11)	0.0017 (11)
C11	0.0585 (17)	0.0363 (14)	0.0412 (14)	0.0086 (13)	0.0136 (13)	−0.0008 (11)
C12	0.0406 (15)	0.0534 (16)	0.0490 (16)	0.0000 (13)	0.0149 (12)	0.0109 (13)
C13	0.0452 (15)	0.0554 (17)	0.0435 (15)	0.0153 (13)	0.0166 (12)	0.0060 (13)
C14	0.0346 (14)	0.0347 (14)	0.074 (2)	0.0021 (11)	0.0089 (13)	0.0009 (13)
C15	0.0343 (13)	0.0351 (13)	0.0604 (17)	0.0018 (11)	0.0107 (12)	−0.0027 (12)
C16	0.0293 (14)	0.0547 (19)	0.097 (3)	0.0095 (13)	0.0075 (16)	0.0062 (18)
C17	0.0551 (18)	0.0295 (13)	0.0676 (19)	0.0070 (12)	0.0177 (15)	−0.0009 (13)
C18	0.0523 (18)	0.0429 (16)	0.071 (2)	0.0222 (14)	0.0174 (15)	0.0094 (14)
C19	0.0419 (14)	0.0368 (13)	0.0467 (15)	−0.0030 (11)	0.0157 (12)	−0.0055 (11)
C20	0.0361 (13)	0.0458 (15)	0.0473 (15)	−0.0007 (11)	0.0140 (12)	−0.0021 (12)
C21	0.0442 (16)	0.0507 (16)	0.0422 (15)	0.0023 (13)	0.0082 (12)	−0.0080 (12)
C22	0.0504 (17)	0.0507 (16)	0.0545 (17)	−0.0018 (13)	0.0244 (14)	0.0044 (14)
C23	0.0555 (17)	0.0479 (16)	0.0425 (15)	0.0132 (13)	0.0172 (13)	0.0035 (12)

Geometric parameters (Å, º) top

Br1—C5	1.899 (2)	C8—H8	0.9300
Ni1—O3ⁱ	1.9963 (16)	C9—C11	1.384 (4)
Ni1—N2	2.1439 (19)	C9—H9	0.9300
Ni1—O2	2.1655 (17)	C10—C12	1.368 (4)
Ni1—O1	2.2024 (17)	C10—H10	0.9300
Ni1—N1	2.204 (2)	C11—C13	1.362 (4)
Ni1—N3	2.204 (2)	C11—H11	0.9300
O1—C1	1.264 (3)	C12—C13	1.377 (4)
N1—C9	1.336 (3)	C12—H12	0.9300
N1—C10	1.345 (3)	C13—H13	0.9300
C1—O2	1.259 (3)	C14—C16	1.380 (4)
C1—C7	1.496 (3)	C14—H14	0.9300
N2—C14	1.318 (3)	C15—C17	1.377 (4)
N2—C15	1.330 (3)	C15—H15	0.9300
C2—O4	1.226 (3)	C16—C18	1.363 (5)
C2—O3	1.282 (3)	C16—H16	0.9300
C2—C3	1.511 (3)	C17—C18	1.373 (4)
O3—Ni1ⁱⁱ	1.9962 (16)	C17—H17	0.9300
N3—C20	1.335 (3)	C18—H18	0.9300
N3—C19	1.341 (3)	C19—C21	1.375 (4)
C3—C8	1.381 (3)	C19—H19	0.9300
C3—C4	1.390 (3)	C20—C22	1.386 (4)
C4—C5	1.381 (3)	C20—H20	0.9300
C4—H4	0.9300	C21—C23	1.372 (4)
C5—C6	1.380 (3)	C21—H21	0.9300
C6—C7	1.390 (3)	C22—C23	1.383 (4)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.387 (3)	C23—H23	0.9300

O3ⁱ—Ni1—N2	94.29 (7)	C3—C8—C7	121.0 (2)
O3ⁱ—Ni1—O2	112.73 (7)	C3—C8—H8	119.5
N2—Ni1—O2	152.98 (7)	C7—C8—H8	119.5
O3ⁱ—Ni1—O1	172.84 (7)	N1—C9—C11	123.7 (3)
N2—Ni1—O1	92.78 (7)	N1—C9—H9	118.2
O2—Ni1—O1	60.20 (6)	C11—C9—H9	118.2
O3ⁱ—Ni1—N1	88.82 (7)	N1—C10—C12	123.4 (3)
N2—Ni1—N1	90.11 (7)	N1—C10—H10	118.3
O2—Ni1—N1	90.48 (7)	C12—C10—H10	118.3
O1—Ni1—N1	90.02 (7)	C13—C11—C9	119.1 (3)
O3ⁱ—Ni1—N3	90.39 (7)	C13—C11—H11	120.5
N2—Ni1—N3	91.78 (7)	C9—C11—H11	120.5
O2—Ni1—N3	88.13 (7)	C10—C12—C13	119.4 (3)
O1—Ni1—N3	90.54 (7)	C10—C12—H12	120.3
N1—Ni1—N3	178.00 (7)	C13—C12—H12	120.3
C1—O1—Ni1	88.74 (14)	C11—C13—C12	118.3 (3)
C9—N1—C10	116.1 (2)	C11—C13—H13	120.9
C9—N1—Ni1	124.07 (17)	C12—C13—H13	120.9
C10—N1—Ni1	119.51 (17)	N2—C14—C16	123.8 (3)
O2—C1—O1	120.5 (2)	N2—C14—H14	118.1
O2—C1—C7	119.7 (2)	C16—C14—H14	118.1
O1—C1—C7	119.7 (2)	N2—C15—C17	123.3 (3)
C1—O2—Ni1	90.54 (14)	N2—C15—H15	118.4
C14—N2—C15	117.1 (2)	C17—C15—H15	118.4
C14—N2—Ni1	118.52 (17)	C18—C16—C14	118.4 (3)
C15—N2—Ni1	124.42 (17)	C18—C16—H16	120.8
O4—C2—O3	125.9 (2)	C14—C16—H16	120.8
O4—C2—C3	119.5 (2)	C18—C17—C15	118.5 (3)
O3—C2—C3	114.5 (2)	C18—C17—H17	120.8
C2—O3—Ni1ⁱⁱ	130.29 (15)	C15—C17—H17	120.8
C20—N3—C19	116.3 (2)	C16—C18—C17	119.0 (3)
C20—N3—Ni1	122.15 (17)	C16—C18—H18	120.5
C19—N3—Ni1	121.10 (17)	C17—C18—H18	120.5
C8—C3—C4	119.5 (2)	N3—C19—C21	124.0 (3)
C8—C3—C2	121.0 (2)	N3—C19—H19	118.0
C4—C3—C2	119.5 (2)	C21—C19—H19	118.0
C5—C4—C3	119.2 (2)	N3—C20—C22	123.4 (3)
C5—C4—H4	120.4	N3—C20—H20	118.3
C3—C4—H4	120.4	C22—C20—H20	118.3
C6—C5—C4	121.8 (2)	C23—C21—C19	119.1 (3)
C6—C5—Br1	119.11 (17)	C23—C21—H21	120.4
C4—C5—Br1	119.06 (17)	C19—C21—H21	120.4
C5—C6—C7	118.8 (2)	C23—C22—C20	119.1 (3)
C5—C6—H6	120.6	C23—C22—H22	120.5
C7—C6—H6	120.6	C20—C22—H22	120.5
C8—C7—C6	119.7 (2)	C21—C23—C22	118.1 (3)
C8—C7—C1	120.1 (2)	C21—C23—H23	120.9
C6—C7—C1	120.1 (2)	C22—C23—H23	121.0

N2—Ni1—O1—C1	179.66 (14)	O4—C2—C3—C4	2.8 (3)
O2—Ni1—O1—C1	0.32 (13)	O3—C2—C3—C4	−175.6 (2)
N1—Ni1—O1—C1	−90.23 (14)	C8—C3—C4—C5	−0.3 (3)
N3—Ni1—O1—C1	87.85 (14)	C2—C3—C4—C5	−179.8 (2)
O3ⁱ—Ni1—N1—C9	−146.9 (2)	C3—C4—C5—C6	0.1 (4)
N2—Ni1—N1—C9	118.8 (2)	C3—C4—C5—Br1	−179.01 (17)
O2—Ni1—N1—C9	−34.2 (2)	C4—C5—C6—C7	0.0 (4)
O1—Ni1—N1—C9	26.0 (2)	Br1—C5—C6—C7	179.19 (17)
O3ⁱ—Ni1—N1—C10	26.11 (19)	C5—C6—C7—C8	−0.1 (3)
N2—Ni1—N1—C10	−68.18 (19)	C5—C6—C7—C1	−178.3 (2)
O2—Ni1—N1—C10	138.84 (19)	O2—C1—C7—C8	−0.3 (3)
O1—Ni1—N1—C10	−160.96 (18)	O1—C1—C7—C8	−179.3 (2)
Ni1—O1—C1—O2	−0.5 (2)	O2—C1—C7—C6	177.9 (2)
Ni1—O1—C1—C7	178.45 (19)	O1—C1—C7—C6	−1.1 (3)
O1—C1—O2—Ni1	0.6 (2)	C4—C3—C8—C7	0.2 (3)
C7—C1—O2—Ni1	−178.44 (19)	C2—C3—C8—C7	179.8 (2)
O3ⁱ—Ni1—O2—C1	178.35 (13)	C6—C7—C8—C3	0.0 (3)
N2—Ni1—O2—C1	−1.8 (2)	C1—C7—C8—C3	178.2 (2)
O1—Ni1—O2—C1	−0.32 (13)	C10—N1—C9—C11	−2.0 (4)
N1—Ni1—O2—C1	89.43 (14)	Ni1—N1—C9—C11	171.2 (2)
N3—Ni1—O2—C1	−92.01 (14)	C9—N1—C10—C12	1.8 (4)
O3ⁱ—Ni1—N2—C14	−174.3 (2)	Ni1—N1—C10—C12	−171.7 (2)
O2—Ni1—N2—C14	5.8 (3)	N1—C9—C11—C13	0.0 (4)
O1—Ni1—N2—C14	4.6 (2)	N1—C10—C12—C13	0.4 (4)
N1—Ni1—N2—C14	−85.5 (2)	C9—C11—C13—C12	2.3 (4)
N3—Ni1—N2—C14	95.2 (2)	C10—C12—C13—C11	−2.5 (4)
O3ⁱ—Ni1—N2—C15	6.8 (2)	C15—N2—C14—C16	0.3 (5)
O2—Ni1—N2—C15	−173.11 (19)	Ni1—N2—C14—C16	−178.7 (3)
O1—Ni1—N2—C15	−174.4 (2)	C14—N2—C15—C17	0.9 (4)
N1—Ni1—N2—C15	95.6 (2)	Ni1—N2—C15—C17	179.8 (2)
N3—Ni1—N2—C15	−83.7 (2)	N2—C14—C16—C18	−1.0 (6)
O4—C2—O3—Ni1ⁱⁱ	−0.5 (4)	N2—C15—C17—C18	−1.3 (5)
C3—C2—O3—Ni1ⁱⁱ	177.90 (14)	C14—C16—C18—C17	0.5 (5)
O3ⁱ—Ni1—N3—C20	175.21 (19)	C15—C17—C18—C16	0.6 (5)
N2—Ni1—N3—C20	−90.49 (19)	C20—N3—C19—C21	−1.2 (4)
O2—Ni1—N3—C20	62.47 (19)	Ni1—N3—C19—C21	171.5 (2)
O1—Ni1—N3—C20	2.31 (19)	C19—N3—C20—C22	1.4 (4)
O3ⁱ—Ni1—N3—C19	2.84 (19)	Ni1—N3—C20—C22	−171.3 (2)
N2—Ni1—N3—C19	97.14 (19)	N3—C19—C21—C23	−0.1 (4)
O2—Ni1—N3—C19	−109.90 (19)	N3—C20—C22—C23	−0.1 (4)
O1—Ni1—N3—C19	−170.06 (18)	C19—C21—C23—C22	1.4 (4)
O4—C2—C3—C8	−176.7 (2)	C20—C22—C23—C21	−1.3 (4)
O3—C2—C3—C8	4.8 (3)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₃BrO₄)(C₅H₅N)₃]
M_r	539.02
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	19.6621 (6), 16.0190 (6), 14.8755 (5)
β (°)	111.504 (2)
V (Å³)	4359.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.76
Crystal size (mm)	0.22 × 0.20 × 0.08

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.582, 0.809
No. of measured, independent and observed [I > 2σ(I)] reflections	22727, 5402, 4195
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.05
No. of reflections	5402
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.34

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Br1—C5	1.899 (2)	Ni1—O2	2.1655 (17)
Ni1—N2	2.1439 (19)	Ni1—O1	2.2024 (17)

N2—Ni1—O2	152.98 (7)	O1—Ni1—N1	90.02 (7)
N2—Ni1—O1	92.78 (7)	N2—Ni1—N3	91.78 (7)
O2—Ni1—O1	60.20 (6)	O2—Ni1—N3	88.13 (7)
N2—Ni1—N1	90.11 (7)	O1—Ni1—N3	90.54 (7)
O2—Ni1—N1	90.48 (7)	N1—Ni1—N3	178.00 (7)

Acknowledgements

The author is grateful to Professor D. Wang for his help.

References

Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Therrien, B., Vieille-Petit, L. & Suss-Fink, G. (2005). J. Mol. Struct. 749, 183–186. Web of Science CSD CrossRef CAS Google Scholar