Poly[aqua[μ2-1,2-bis­(imidazol-1-yl­methyl)benzene-κ2N3:N3′](μ2-5-bromo­benzene-1,3-dicarboxyl­ato-κ3O1,O1′:O3)nickel(II)]

Zhu, K.; Chen, H.; Liu, G.-X.

doi:10.1107/S1600536809016286

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m623

doi:10.1107/S1600536809016286

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Poly[aqua[μ₂-1,2-bis(imidazol-1-ylmethyl)benzene-κ²N³:N^3′](μ₂-5-bromobenzene-1,3-dicarboxylato-κ³O¹,O^1′:O³)nickel(II)]

Kun Zhu,^a Hong Chen ^a and Guang-Xiang Liu ^a ^*

^aAnhui Key Laboratory of Functional Coordination Compounds, School of Chemistry and Chemical Engineering, Anqing Normal University, Anqing 246003, People's Republic of China
^*Correspondence e-mail: liugx@live.com

(Received 29 April 2009; accepted 30 April 2009; online 7 May 2009)

In the two-dimensional title coordination polymer, [Ni(C₈H₃BrO₄)(C₁₄H₁₄N₄)(H₂O)]_n, the Ni^II atom adopts a distorted octahedral geometry, being ligated by three O atoms from two different 5-bromobenzene-1,3-dicarboxylate ligands, two N atoms from two 1,2-bis(imidazol-1-ylmethyl)benzene ligands and one coordinated water molecule. The Ni atoms are bridged by the 5-bromobenzene-1,3-dicarboxylate ligands, forming chains, which are further linked by 1,2-bis(imidazol-1-ylmethyl)benzene, generating a layer structure parallel to (001).

Related literature

For general background to self-assembly coordination polymers with metal ions and bis(imidazole) ligands interconnected by flexible spacers, see: Qi et al. (2008 ); Liu et al. (2009 ). For the role played by different organic anions in directing the final structure and topology, see: Hu et al. (2008 ). For related structures, see: Liu et al. (2008 ).

Experimental

Crystal data

[Ni(C₈H₃BrO₄)(C₁₄H₁₄N₄)(H₂O)]
M_r = 558.03
Triclinic, $[P \overline 1]$
a = 9.1374 (12) Å
b = 10.1394 (14) Å
c = 12.9642 (18) Å
α = 80.046 (2)°
β = 83.233 (2)°
γ = 70.004 (2)°
V = 1109.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.72 mm⁻¹
T = 293 K
0.26 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS: Bruker, 1997 ) T_min = 0.538, T_max = 0.641
8172 measured reflections
4055 independent reflections
3029 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.085
S = 1.04
4055 reflections
291 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −1.12 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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/S1600536809016286/at2774sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016286/at2774Isup2.hkl

checkCIF report

Comment top

The self-assembly of coordination polymers has attracted considerable attention in the past decade. This arises mainly for their various intriguing topological structures and their potential applications in material chemistry. Recently significant work has been carried out by using metal ions assembly with bis(imidazole) ligands interconnected by flexible spacers (Qi et al., 2008; Liu et al., 2009). From careful inspection of the reported cases, we found that: the ligand exhibits a special ability to formulate the compounds, and different organic anions play an important role in directing the final structures and topologies (Hu et al., 2008). Inspired by the aftermentioned considerations, 1,2-bis(imidazol-1-ylmethyl)benzene was chosen as neutral ligands, 5-bromobenzene-1,3-dicarboxylate were chosen as co-ligands to construct the title complex (I).

The title coordination polymer is a two-dimensional layer coordination polymer. The Ni^II atom adopts a distorted octahedral geometry, being ligated by three O atoms from two different 5-bromobenzene-1,3-dicarboxylate ligand, two N atoms from two 1,2-bis(imidazol-1-ylmethyl)benzene and one coordinated water molecule, as shown in Fig. 1. The Ni atoms are bridged by 5-bromobenzene-1,3-dicarboxylate ligand to form one-dimensional chain, which are further linked by 1,2-bis(imidazol-1-ylmethyl)benzene to generate a two-dimensional layer structure, as shown in Fig. 2.

Related literature top

For general background to self-assembly coordination polymers with metal ions and bis(imidazole) ligands interconnected by flexible spacers, see: Qi et al. (2008); Liu et al. (2009). For the role played by different organic anions in directing the final structure and topology, see: Hu et al. (2008). For related structures, see: Liu et al. (2008).

Experimental top

A mixture of Ni(NO₃)_2.6H₂O (58.2 mg, 0.2 mmol), 5-bromobenzene-1,3-dicarboxylate acid (33.0 mg, 0.1 mmol), 1,2-bis(imidazol-1-ylmethyl)benzene (23.8 mg, 0.1 mmol), NaOH (8 mg, 0.2 mmol) and H₂O (15 ml) was added in a Teflon-lined stainless steel vessel. The vessel was sealed and heated for 3 d at 433 K. After the mixture was slowly cooled to room temperature, green block crystals were obtained in the yield of ca 67% based on Ni.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 asymmetric unit of the title compound, extended to show the Ni coordination. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) x - 1, y + 1, z; (ii) x, y - 1, z.]
	Fig. 2. The two-dimensional layer structure of the title compound.

Poly[aqua[µ₂-1,2-bis(imidazol-1-ylmethyl)benzene- κ²N³:N^3'](µ₂-5-bromobenzene-1,3-dicarboxylato- κ³O¹,O^1':O³)nickel(II)] top

Crystal data top

[Ni(C₈H₃BrO₄)(C₁₄H₁₄N₄)(H₂O)]	Z = 2
M_r = 558.03	F(000) = 564
Triclinic, P1	D_x = 1.670 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1374 (12) Å	Cell parameters from 2114 reflections
b = 10.1394 (14) Å	θ = 2.4–24.0°
c = 12.9642 (18) Å	µ = 2.72 mm⁻¹
α = 80.046 (2)°	T = 293 K
β = 83.233 (2)°	Block, green
γ = 70.004 (2)°	0.26 × 0.20 × 0.18 mm
V = 1109.5 (3) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4055 independent reflections
Radiation source: sealed tube	3029 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS: Bruker, 1997)	h = −11→9
T_min = 0.538, T_max = 0.641	k = −12→11
8172 measured reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.029P)² + 0.735P] where P = (F_o² + 2F_c²)/3
4055 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −1.12 e Å⁻³

Crystal data top

[Ni(C₈H₃BrO₄)(C₁₄H₁₄N₄)(H₂O)]	γ = 70.004 (2)°
M_r = 558.03	V = 1109.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.1374 (12) Å	Mo Kα radiation
b = 10.1394 (14) Å	µ = 2.72 mm⁻¹
c = 12.9642 (18) Å	T = 293 K
α = 80.046 (2)°	0.26 × 0.20 × 0.18 mm
β = 83.233 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4055 independent reflections
Absorption correction: multi-scan (SADABS: Bruker, 1997)	3029 reflections with I > 2σ(I)
T_min = 0.538, T_max = 0.641	R_int = 0.029
8172 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.64 e Å⁻³
4055 reflections	Δρ_min = −1.12 e Å⁻³
291 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
Ni1	−0.11002 (5)	0.18147 (4)	0.34656 (3)	0.02475 (13)
N1	0.1280 (3)	0.0814 (3)	0.3229 (2)	0.0286 (7)
N2	0.3530 (3)	−0.0730 (3)	0.2776 (2)	0.0332 (7)
N3	0.4261 (3)	−0.5489 (3)	0.3554 (2)	0.0372 (8)
N4	0.6546 (3)	−0.7159 (3)	0.3708 (2)	0.0313 (7)
O1	−0.0886 (3)	0.3683 (2)	0.27370 (18)	0.0326 (6)
O2	−0.0881 (4)	0.4666 (3)	0.4146 (2)	0.0581 (9)
O3	−0.1442 (3)	0.9777 (2)	0.37521 (17)	0.0287 (5)
O4	−0.1529 (3)	1.0986 (2)	0.21699 (17)	0.0308 (6)
O1W	−0.0840 (3)	0.2116 (3)	0.4966 (2)	0.0341 (7)
Br1	−0.14928 (6)	0.76345 (5)	−0.06669 (3)	0.06060 (18)
C1	−0.0961 (4)	0.4705 (3)	0.3195 (3)	0.0282 (8)
C2	−0.1196 (4)	0.6114 (3)	0.2502 (3)	0.0251 (8)
C3	−0.1282 (4)	0.6229 (4)	0.1422 (3)	0.0291 (8)
H3	−0.1227	0.5444	0.1120	0.035*
C4	−0.1448 (4)	0.7516 (4)	0.0806 (3)	0.0306 (8)
C5	−0.1547 (4)	0.8709 (4)	0.1226 (3)	0.0309 (8)
H5	−0.1661	0.9569	0.0796	0.037*
C6	−0.1473 (4)	0.8599 (3)	0.2307 (3)	0.0239 (7)
C7	−0.1303 (4)	0.7308 (3)	0.2944 (3)	0.0242 (7)
H7	−0.1260	0.7240	0.3665	0.029*
C8	−0.1508 (4)	0.9869 (3)	0.2772 (3)	0.0247 (8)
C9	0.2459 (5)	0.1249 (4)	0.3411 (3)	0.0454 (11)
H9	0.2329	0.2076	0.3682	0.055*
C10	0.3845 (5)	0.0317 (4)	0.3144 (3)	0.0489 (11)
H10	0.4826	0.0376	0.3199	0.059*
C11	0.1973 (4)	−0.0380 (4)	0.2842 (3)	0.0342 (9)
H11	0.1444	−0.0919	0.2638	0.041*
C12	0.4673 (4)	−0.2047 (4)	0.2455 (3)	0.0468 (11)
H12A	0.4975	−0.2743	0.3074	0.056*
H12B	0.5601	−0.1848	0.2128	0.056*
C13	0.4039 (4)	−0.2660 (4)	0.1699 (3)	0.0388 (10)
C14	0.4232 (5)	−0.2198 (5)	0.0633 (4)	0.0578 (12)
H14	0.4746	−0.1540	0.0412	0.069*
C15	0.3664 (5)	−0.2713 (5)	−0.0108 (4)	0.060
H15	0.3765	−0.2380	−0.0819	0.072*
C16	0.2960 (4)	−0.3706 (3)	0.0223 (3)	0.060
H16	0.2594	−0.4069	−0.0267	0.072*
C17	0.2782 (4)	−0.4182 (3)	0.1269 (3)	0.0678 (15)
H17	0.2305	−0.4871	0.1477	0.081*
C18	0.3299 (4)	−0.3658 (4)	0.2031 (3)	0.0427 (10)
C19	0.3027 (5)	−0.4184 (4)	0.3173 (4)	0.0550 (12)
H19A	0.2961	−0.3452	0.3587	0.066*
H19B	0.2035	−0.4356	0.3275	0.066*
C20	0.5718 (4)	−0.6006 (4)	0.3131 (3)	0.0400 (10)
H20	0.6095	−0.5598	0.2505	0.048*
C21	0.5557 (5)	−0.7398 (4)	0.4541 (3)	0.0456 (10)
H21	0.5813	−0.8154	0.5082	0.055*
C22	0.4150 (5)	−0.6367 (5)	0.4458 (3)	0.0491 (11)
H22	0.3280	−0.6278	0.4926	0.059*
H1WA	−0.067 (5)	0.285 (5)	0.483 (3)	0.059 (16)*
H1WB	−0.008 (5)	0.158 (4)	0.529 (3)	0.047 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0333 (3)	0.0136 (2)	0.0266 (2)	−0.00590 (19)	−0.00584 (19)	−0.00212 (18)
N1	0.0322 (18)	0.0215 (16)	0.0319 (16)	−0.0074 (14)	−0.0049 (13)	−0.0040 (13)
N2	0.0253 (18)	0.0315 (18)	0.0413 (18)	−0.0055 (14)	−0.0041 (14)	−0.0079 (14)
N3	0.0277 (18)	0.0291 (18)	0.048 (2)	−0.0014 (14)	−0.0009 (15)	−0.0063 (15)
N4	0.0332 (18)	0.0224 (17)	0.0362 (17)	−0.0061 (14)	−0.0031 (14)	−0.0044 (14)
O1	0.0496 (16)	0.0163 (12)	0.0325 (13)	−0.0115 (12)	−0.0013 (12)	−0.0046 (10)
O2	0.118 (3)	0.0240 (15)	0.0365 (16)	−0.0248 (16)	−0.0304 (17)	0.0041 (12)
O3	0.0397 (15)	0.0172 (12)	0.0281 (13)	−0.0078 (11)	−0.0057 (11)	−0.0015 (10)
O4	0.0452 (16)	0.0179 (13)	0.0313 (13)	−0.0116 (12)	−0.0099 (11)	−0.0011 (10)
O1W	0.0465 (19)	0.0231 (16)	0.0311 (15)	−0.0087 (15)	−0.0100 (13)	−0.0006 (12)
Br1	0.1137 (5)	0.0440 (3)	0.0264 (2)	−0.0292 (3)	−0.0036 (2)	−0.00487 (19)
C1	0.035 (2)	0.0182 (19)	0.032 (2)	−0.0078 (16)	−0.0067 (16)	−0.0026 (15)
C2	0.0250 (19)	0.0179 (18)	0.0340 (19)	−0.0079 (15)	−0.0046 (15)	−0.0045 (15)
C3	0.036 (2)	0.0230 (19)	0.0308 (19)	−0.0107 (16)	−0.0016 (16)	−0.0076 (15)
C4	0.041 (2)	0.029 (2)	0.0225 (18)	−0.0123 (17)	−0.0039 (16)	−0.0030 (15)
C5	0.043 (2)	0.0176 (18)	0.0308 (19)	−0.0116 (17)	−0.0045 (17)	0.0044 (15)
C6	0.0235 (19)	0.0167 (17)	0.0319 (19)	−0.0069 (15)	−0.0033 (15)	−0.0031 (14)
C7	0.0260 (19)	0.0187 (18)	0.0283 (18)	−0.0070 (15)	−0.0077 (15)	−0.0016 (14)
C8	0.0231 (19)	0.0146 (18)	0.035 (2)	−0.0040 (14)	−0.0050 (15)	−0.0012 (15)
C9	0.047 (3)	0.037 (2)	0.062 (3)	−0.018 (2)	−0.005 (2)	−0.018 (2)
C10	0.038 (3)	0.050 (3)	0.067 (3)	−0.022 (2)	−0.004 (2)	−0.016 (2)
C11	0.030 (2)	0.029 (2)	0.046 (2)	−0.0084 (17)	−0.0084 (17)	−0.0067 (17)
C12	0.026 (2)	0.046 (3)	0.063 (3)	0.0006 (19)	−0.003 (2)	−0.018 (2)
C13	0.031 (2)	0.035 (2)	0.041 (2)	0.0059 (18)	−0.0073 (18)	−0.0122 (19)
C14	0.063 (3)	0.037 (3)	0.056 (3)	0.003 (2)	−0.004 (2)	−0.001 (2)
C15	0.059	0.050	0.054	0.015	−0.024	−0.016
C16	0.059	0.050	0.054	0.015	−0.024	−0.016
C17	0.038 (3)	0.050 (3)	0.115 (5)	−0.002 (2)	−0.015 (3)	−0.029 (3)
C18	0.025 (2)	0.034 (2)	0.061 (3)	0.0076 (18)	−0.0108 (19)	−0.013 (2)
C19	0.032 (2)	0.039 (3)	0.079 (3)	0.003 (2)	0.007 (2)	−0.003 (2)
C20	0.035 (2)	0.032 (2)	0.045 (2)	−0.0026 (19)	0.0000 (19)	−0.0001 (19)
C21	0.049 (3)	0.044 (3)	0.040 (2)	−0.015 (2)	−0.002 (2)	0.0038 (19)
C22	0.044 (3)	0.054 (3)	0.046 (3)	−0.016 (2)	0.005 (2)	−0.005 (2)

Geometric parameters (Å, º) top

Ni1—O1	2.027 (2)	C4—C5	1.381 (5)
Ni1—N4ⁱ	2.057 (3)	C5—C6	1.395 (5)
Ni1—N1	2.072 (3)	C5—H5	0.9300
Ni1—O1W	2.073 (3)	C6—C7	1.392 (4)
Ni1—O4ⁱⁱ	2.133 (2)	C6—C8	1.503 (4)
Ni1—O3ⁱⁱ	2.157 (2)	C7—H7	0.9300
Ni1—C8ⁱⁱ	2.456 (3)	C8—Ni1^iv	2.456 (3)
N1—C11	1.315 (4)	C9—C10	1.345 (5)
N1—C9	1.354 (4)	C9—H9	0.9300
N2—C11	1.339 (4)	C10—H10	0.9300
N2—C10	1.361 (5)	C11—H11	0.9300
N2—C12	1.478 (4)	C12—C13	1.508 (5)
N3—C20	1.341 (4)	C12—H12A	0.9700
N3—C22	1.360 (5)	C12—H12B	0.9700
N3—C19	1.466 (5)	C13—C18	1.383 (6)
N4—C20	1.314 (4)	C13—C14	1.392 (6)
N4—C21	1.368 (5)	C14—C15	1.393 (6)
N4—Ni1ⁱⁱⁱ	2.057 (3)	C14—H14	0.9300
O1—C1	1.260 (4)	C15—C16	1.357 (6)
O2—C1	1.237 (4)	C15—H15	0.9300
O3—C8	1.264 (4)	C16—C17	1.368 (6)
O3—Ni1^iv	2.157 (2)	C16—H16	0.9300
O4—C8	1.255 (4)	C17—C18	1.395 (5)
O4—Ni1^iv	2.133 (2)	C17—H17	0.9300
O1W—H1WA	0.80 (5)	C18—C19	1.507 (6)
O1W—H1WB	0.82 (4)	C19—H19A	0.9700
Br1—C4	1.897 (3)	C19—H19B	0.9700
C1—C2	1.512 (5)	C20—H20	0.9300
C2—C3	1.394 (4)	C21—C22	1.353 (5)
C2—C7	1.396 (4)	C21—H21	0.9300
C3—C4	1.377 (5)	C22—H22	0.9300
C3—H3	0.9300

O1—Ni1—N4ⁱ	88.51 (11)	C6—C7—C2	120.1 (3)
O1—Ni1—N1	90.67 (10)	C6—C7—H7	119.9
N4ⁱ—Ni1—N1	178.90 (11)	C2—C7—H7	119.9
O1—Ni1—O1W	95.91 (11)	O4—C8—O3	121.2 (3)
N4ⁱ—Ni1—O1W	87.85 (12)	O4—C8—C6	118.9 (3)
N1—Ni1—O1W	91.50 (11)	O3—C8—C6	119.8 (3)
O1—Ni1—O4ⁱⁱ	100.66 (9)	O4—C8—Ni1^iv	60.26 (16)
N4ⁱ—Ni1—O4ⁱⁱ	90.21 (10)	O3—C8—Ni1^iv	61.33 (16)
N1—Ni1—O4ⁱⁱ	90.66 (10)	C6—C8—Ni1^iv	170.6 (2)
O1W—Ni1—O4ⁱⁱ	163.26 (11)	C10—C9—N1	110.4 (3)
O1—Ni1—O3ⁱⁱ	162.21 (9)	C10—C9—H9	124.8
N4ⁱ—Ni1—O3ⁱⁱ	91.35 (10)	N1—C9—H9	124.8
N1—Ni1—O3ⁱⁱ	89.66 (10)	C9—C10—N2	106.4 (3)
O1W—Ni1—O3ⁱⁱ	101.87 (10)	C9—C10—H10	126.8
O4ⁱⁱ—Ni1—O3ⁱⁱ	61.55 (9)	N2—C10—H10	126.8
O1—Ni1—C8ⁱⁱ	131.29 (10)	N1—C11—N2	112.2 (3)
N4ⁱ—Ni1—C8ⁱⁱ	93.07 (11)	N1—C11—H11	123.9
N1—Ni1—C8ⁱⁱ	88.03 (11)	N2—C11—H11	123.9
O1W—Ni1—C8ⁱⁱ	132.80 (12)	N2—C12—C13	112.5 (3)
O4ⁱⁱ—Ni1—C8ⁱⁱ	30.73 (9)	N2—C12—H12A	109.1
O3ⁱⁱ—Ni1—C8ⁱⁱ	30.95 (9)	C13—C12—H12A	109.1
C11—N1—C9	104.8 (3)	N2—C12—H12B	109.1
C11—N1—Ni1	127.0 (2)	C13—C12—H12B	109.1
C9—N1—Ni1	128.2 (2)	H12A—C12—H12B	107.8
C11—N2—C10	106.2 (3)	C18—C13—C14	120.0 (4)
C11—N2—C12	126.8 (3)	C18—C13—C12	122.4 (4)
C10—N2—C12	126.9 (3)	C14—C13—C12	117.6 (4)
C20—N3—C22	106.9 (3)	C15—C14—C13	120.7 (5)
C20—N3—C19	127.8 (3)	C15—C14—H14	119.7
C22—N3—C19	125.2 (3)	C13—C14—H14	119.7
C20—N4—C21	105.2 (3)	C16—C15—C14	119.0 (4)
C20—N4—Ni1ⁱⁱⁱ	125.5 (3)	C16—C15—H15	120.5
C21—N4—Ni1ⁱⁱⁱ	128.8 (3)	C14—C15—H15	120.5
C1—O1—Ni1	124.9 (2)	C15—C16—C17	120.9 (3)
C8—O3—Ni1^iv	87.72 (19)	C15—C16—H16	119.6
C8—O4—Ni1^iv	89.01 (19)	C17—C16—H16	119.6
Ni1—O1W—H1WA	99 (3)	C16—C17—C18	121.5 (3)
Ni1—O1W—H1WB	120 (3)	C16—C17—H17	119.3
H1WA—O1W—H1WB	104 (4)	C18—C17—H17	119.2
O2—C1—O1	126.4 (3)	C13—C18—C17	118.0 (4)
O2—C1—C2	117.8 (3)	C13—C18—C19	122.7 (4)
O1—C1—C2	115.9 (3)	C17—C18—C19	119.3 (4)
C3—C2—C7	119.6 (3)	N3—C19—C18	112.9 (3)
C3—C2—C1	120.7 (3)	N3—C19—H19A	109.0
C7—C2—C1	119.8 (3)	C18—C19—H19A	109.0
C4—C3—C2	119.3 (3)	N3—C19—H19B	109.0
C4—C3—H3	120.3	C18—C19—H19B	109.0
C2—C3—H3	120.3	H19A—C19—H19B	107.8
C3—C4—C5	122.1 (3)	N4—C20—N3	111.8 (3)
C3—C4—Br1	118.7 (2)	N4—C20—H20	124.1
C5—C4—Br1	119.3 (3)	N3—C20—H20	124.1
C4—C5—C6	118.7 (3)	C22—C21—N4	109.7 (4)
C4—C5—H5	120.7	C22—C21—H21	125.1
C6—C5—H5	120.7	N4—C21—H21	125.1
C7—C6—C5	120.2 (3)	C21—C22—N3	106.4 (4)
C7—C6—C8	120.3 (3)	C21—C22—H22	126.8
C5—C6—C8	119.5 (3)	N3—C22—H22	126.8

O1—Ni1—N1—C11	−131.0 (3)	C7—C6—C8—O3	−2.7 (5)
N4ⁱ—Ni1—N1—C11	−173 (47)	C5—C6—C8—O3	179.9 (3)
O1W—Ni1—N1—C11	133.1 (3)	C7—C6—C8—Ni1^iv	91.6 (15)
O4ⁱⁱ—Ni1—N1—C11	−30.3 (3)	C5—C6—C8—Ni1^iv	−85.7 (15)
O3ⁱⁱ—Ni1—N1—C11	31.2 (3)	C11—N1—C9—C10	−0.5 (5)
C8ⁱⁱ—Ni1—N1—C11	0.3 (3)	Ni1—N1—C9—C10	−179.1 (3)
O1—Ni1—N1—C9	47.3 (3)	N1—C9—C10—N2	0.4 (5)
N4ⁱ—Ni1—N1—C9	5 (6)	C11—N2—C10—C9	−0.1 (5)
O1W—Ni1—N1—C9	−48.6 (3)	C12—N2—C10—C9	−175.4 (4)
O4ⁱⁱ—Ni1—N1—C9	148.0 (3)	C9—N1—C11—N2	0.5 (4)
O3ⁱⁱ—Ni1—N1—C9	−150.5 (3)	Ni1—N1—C11—N2	179.1 (2)
C8ⁱⁱ—Ni1—N1—C9	178.6 (3)	C10—N2—C11—N1	−0.2 (4)
N4ⁱ—Ni1—O1—C1	73.7 (3)	C12—N2—C11—N1	175.1 (3)
N1—Ni1—O1—C1	−105.6 (3)	C11—N2—C12—C13	29.1 (5)
O1W—Ni1—O1—C1	−14.0 (3)	C10—N2—C12—C13	−156.5 (4)
O4ⁱⁱ—Ni1—O1—C1	163.6 (3)	N2—C12—C13—C18	−91.9 (4)
O3ⁱⁱ—Ni1—O1—C1	163.4 (3)	N2—C12—C13—C14	88.7 (4)
C8ⁱⁱ—Ni1—O1—C1	166.5 (3)	C18—C13—C14—C15	1.1 (6)
Ni1—O1—C1—O2	14.5 (5)	C12—C13—C14—C15	−179.5 (3)
Ni1—O1—C1—C2	−164.5 (2)	C13—C14—C15—C16	−2.1 (6)
O2—C1—C2—C3	179.4 (3)	C14—C15—C16—C17	1.2 (5)
O1—C1—C2—C3	−1.5 (5)	C15—C16—C17—C18	0.6 (3)
O2—C1—C2—C7	0.5 (5)	C14—C13—C18—C17	0.7 (5)
O1—C1—C2—C7	179.6 (3)	C12—C13—C18—C17	−178.7 (3)
C7—C2—C3—C4	0.9 (5)	C14—C13—C18—C19	−178.9 (3)
C1—C2—C3—C4	−178.0 (3)	C12—C13—C18—C19	1.7 (5)
C2—C3—C4—C5	−0.6 (5)	C16—C17—C18—C13	−1.6 (4)
C2—C3—C4—Br1	177.9 (3)	C16—C17—C18—C19	178.0 (2)
C3—C4—C5—C6	0.1 (6)	C20—N3—C19—C18	20.2 (6)
Br1—C4—C5—C6	−178.4 (3)	C22—N3—C19—C18	−163.9 (4)
C4—C5—C6—C7	0.0 (5)	C13—C18—C19—N3	−94.0 (5)
C4—C5—C6—C8	177.3 (3)	C17—C18—C19—N3	86.4 (4)
C5—C6—C7—C2	0.4 (5)	C21—N4—C20—N3	0.6 (4)
C8—C6—C7—C2	−177.0 (3)	Ni1ⁱⁱⁱ—N4—C20—N3	−172.4 (2)
C3—C2—C7—C6	−0.8 (5)	C22—N3—C20—N4	−0.1 (4)
C1—C2—C7—C6	178.1 (3)	C19—N3—C20—N4	176.4 (4)
Ni1^iv—O4—C8—O3	7.4 (3)	C20—N4—C21—C22	−0.9 (4)
Ni1^iv—O4—C8—C6	−169.3 (3)	Ni1ⁱⁱⁱ—N4—C21—C22	171.8 (3)
Ni1^iv—O3—C8—O4	−7.4 (3)	N4—C21—C22—N3	0.8 (5)
Ni1^iv—O3—C8—C6	169.3 (3)	C20—N3—C22—C21	−0.5 (4)
C7—C6—C8—O4	174.1 (3)	C19—N3—C22—C21	−177.1 (4)
C5—C6—C8—O4	−3.3 (5)

Symmetry codes: (i) x−1, y+1, z; (ii) x, y−1, z; (iii) x+1, y−1, z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₃BrO₄)(C₁₄H₁₄N₄)(H₂O)]
M_r	558.03
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1374 (12), 10.1394 (14), 12.9642 (18)
α, β, γ (°)	80.046 (2), 83.233 (2), 70.004 (2)
V (Å³)	1109.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.72
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS: Bruker, 1997)
T_min, T_max	0.538, 0.641
No. of measured, independent and observed [I > 2σ(I)] reflections	8172, 4055, 3029
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.085, 1.04
No. of reflections	4055
No. of parameters	291
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −1.12

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20731004), the Natural Science Foundation for Outstanding Scholars of Anhui Province, China (grant No. 044-J-04011) and the Natural Science Foundation of Education Commission of Anhui Province, China (No. KJ2008B004).

References

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