Di-μ-thio­cyanato-κ4N:N-bis­({2,4-di­bromo-6-[2-(methyl­amino)ethyl­imino­meth­yl]­phenol­ato-κ3N,N′,O}nickel(II))

Lin, H.-W.

doi:10.1107/S1600536807068146

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m295

doi:10.1107/S1600536807068146

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Di-μ-thiocyanato-κ⁴N:N-bis({2,4-dibromo-6-[2-(methylamino)ethyliminomethyl]phenolato-κ³N,N′,O}nickel(II))

Hong-Wei Lin ^a ^*

^aDepartment of Chemistry, Huaihua University, Huaihua 418008, People's Republic of China
^*Correspondence e-mail: linhongwei1968@126.com

(Received 26 October 2007; accepted 21 December 2007; online 4 January 2008)

The title complex, [Ni₂(C₁₁H₁₁Br₂N₂O)₂(NCS)₂], is a thiocyanate-bridged dinuclear nickel(II) complex. The asymmetric unit contains two molecules. Both Ni atoms in each molecule have a square-pyramidal coordination geometry, and each center is bound by one O and two N atoms of one Schiff base ligand and by one N atom of a bridging thiocyanate ligand, which define the basal planes. N atoms from the bridging thiocyanate ligands occupy the apical positions.

Related literature

For related literature, see: Arıcı et al. (2005 ); Hebbachi & Benali-Cherif (2005 ); Henkel & Krebs (2004 ); Salmon et al. (2005 ); Sarı et al. (2006 ); Tshuva & Lippard (2004 ); Weston (2005 ).

Experimental

Crystal data

[Ni₂(C₁₀H₁₁Br₂N₂O)₂(NCS)₂]
M_r = 451.82
Monoclinic, P 2₁/n
a = 9.2040 (18) Å
b = 19.833 (4) Å
c = 16.319 (3) Å
β = 100.71 (3)°
V = 2927.0 (10) Å³
Z = 8
Mo Kα radiation
μ = 6.92 mm⁻¹
T = 293 (2) K
0.43 × 0.40 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.155, T_max = 0.178 (expected range = 0.063–0.072)
25095 measured reflections
6938 independent reflections
2858 reflections with I > 2σ(I)
R_int = 0.139

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.150
S = 0.94
6938 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.91	2.48	3.269 (9)	146
N5—H5A⋯O1ⁱ	0.91	2.15	3.012 (9)	158
N5—H5A⋯Br2ⁱ	0.91	2.86	3.500 (7)	129
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068146/rn2034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068146/rn2034Isup2.hkl

checkCIF report

Comment top

The design of multidentate ligands and their metallosupramolecular chemistry are of great interest (Henkel & Krebs, 2004; Tshuva & Lippard, 2004; Weston, 2005). Schiff base ligands readily lead to the formation of diverse complexes with most metal ions (Arıcı et al., 2005; Salmon et al., 2005; Hebbachi & Benali-Cherif, 2005; Sarı et al., 2006).

The two Ni centers in the title dinuclear nickel(II) complex are doubly-bridged by thiocyanato ligands. Both Ni atoms are five-coordinate and have square pyramidal geometry but both thiocyanate bridges are asymmetric where the distances are 2.643 (8) and 1.973 (8)Å for Ni1···N6 and Ni1—N3 respectively and 2.589 (8) and 1.978 (7)Å for Ni2···N3 and Ni2—N6 respectively. The Ni···Ni distance is 3.268 (3) Å.

Related literature top

For related literature, see: Arıcı et al. (2005); Hebbachi & Benali-Cherif (2005); Henkel & Krebs (2004); Salmon et al. (2005); Sarı et al. (2006); Tshuva & Lippard (2004); Weston (2005).

Experimental top

3,5-Dibromosalicylaldehyde (1.0 mmol, 280.0 mg), N-methylethane-1,2-diamine (1.0 mmol, 74.0 mg), NH₄NCS (1.0 mmol, 76.0 mg), and Ni(NO₃)₂.6H₂O (1.0 mmol, 290.8 mg) were dissolved in a 50 ml me thanol solution. The mixture was stirred at reflux for half an hour to give a green solution. After keeping the solution in air for 15 days to allow slow evaporation, green block-like crystals were formed.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.

Di-µ-thiocyanato-κ⁴N:N-bis({2,4-dibromo-6-[2- (methylamino)ethyliminomethyl]phenolato-κ³N,N',O}nickel(II)) top

Crystal data top

[Ni₂(C₁₀H₁₁Br₂N₂O)₂(NCS)₂]	F(000) = 1760
M_r = 451.82	D_x = 2.051 Mg m⁻³
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.2040 (18) Å	Cell parameters from 1344 reflections
b = 19.833 (4) Å	θ = 2.4–24.5°
c = 16.319 (3) Å	µ = 6.92 mm⁻¹
β = 100.71 (3)°	T = 293 K
V = 2927.0 (10) Å³	Block, green
Z = 8	0.43 × 0.40 × 0.38 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6938 independent reflections
Radiation source: fine-focus sealed tube	2858 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.139
ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
T_min = 0.155, T_max = 0.178	k = −25→25
25095 measured reflections	l = −21→21

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0506P)²] where P = (F_o² + 2F_c²)/3
6938 reflections	(Δ/σ)_max < 0.001
345 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

[Ni₂(C₁₀H₁₁Br₂N₂O)₂(NCS)₂]	V = 2927.0 (10) Å³
M_r = 451.82	Z = 8
Monoclinic, P21/n	Mo Kα radiation
a = 9.2040 (18) Å	µ = 6.92 mm⁻¹
b = 19.833 (4) Å	T = 293 K
c = 16.319 (3) Å	0.43 × 0.40 × 0.38 mm
β = 100.71 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6938 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2858 reflections with I > 2σ(I)
T_min = 0.155, T_max = 0.178	R_int = 0.139
25095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 0.94	Δρ_max = 0.65 e Å⁻³
6938 reflections	Δρ_min = −0.77 e Å⁻³
345 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	0.59997 (12)	0.01132 (5)	0.24264 (7)	0.0378 (3)
Ni2	0.61799 (12)	0.12004 (5)	0.77631 (7)	0.0349 (3)
Br1	0.41051 (12)	0.33151 (5)	0.43009 (7)	0.0685 (4)
Br2	0.31619 (12)	0.05315 (5)	0.46208 (6)	0.0564 (3)
Br3	0.36394 (13)	0.17932 (5)	1.00163 (7)	0.0669 (4)
Br4	0.37706 (12)	0.45174 (5)	0.90757 (7)	0.0644 (3)
S1	0.8160 (4)	−0.18127 (14)	0.37004 (19)	0.0779 (10)
S2	0.8415 (4)	−0.07194 (15)	0.8944 (2)	0.0851 (10)
O1	0.4903 (6)	0.0452 (3)	0.3223 (4)	0.0440 (16)
O2	0.5198 (6)	0.1600 (3)	0.8571 (3)	0.0468 (16)
N1	0.6349 (8)	0.1003 (3)	0.2016 (4)	0.045 (2)
N2	0.6704 (8)	−0.0212 (4)	0.1394 (4)	0.050 (2)
H2A	0.6074	−0.0543	0.1164	0.060*
N3	0.6368 (8)	−0.0765 (4)	0.2996 (5)	0.049 (2)
N4	0.6322 (8)	0.2040 (3)	0.7179 (5)	0.047 (2)
N5	0.6960 (8)	0.0799 (3)	0.6800 (4)	0.0449 (19)
H5A	0.6473	0.0404	0.6660	0.054*
N6	0.6537 (9)	0.0353 (4)	0.8409 (5)	0.049 (2)
C1	0.5295 (10)	0.1639 (4)	0.3041 (5)	0.041 (2)
C2	0.4755 (10)	0.1078 (4)	0.3426 (5)	0.041 (2)
C3	0.3982 (9)	0.1240 (4)	0.4082 (5)	0.040 (2)
C4	0.3789 (10)	0.1898 (4)	0.4331 (6)	0.047 (2)
H4	0.3275	0.1986	0.4759	0.056*
C5	0.4366 (10)	0.2416 (4)	0.3938 (6)	0.045 (2)
C6	0.5112 (10)	0.2302 (4)	0.3303 (6)	0.052 (3)
H6	0.5497	0.2662	0.3046	0.062*
C7	0.6038 (10)	0.1557 (4)	0.2333 (6)	0.048 (3)
H7	0.6311	0.1950	0.2088	0.057*
C8	0.7089 (11)	0.0998 (5)	0.1295 (6)	0.057 (3)
H8A	0.8153	0.0975	0.1475	0.068*
H8B	0.6848	0.1403	0.0963	0.068*
C9	0.6515 (11)	0.0371 (5)	0.0789 (6)	0.060 (3)
H9A	0.5482	0.0426	0.0537	0.072*
H9B	0.7076	0.0293	0.0351	0.072*
C10	0.7144 (10)	−0.1202 (5)	0.3285 (6)	0.045 (2)
C11	0.5255 (9)	0.2750 (4)	0.8123 (6)	0.041 (2)
C12	0.4913 (9)	0.2237 (4)	0.8649 (5)	0.037 (2)
C13	0.4210 (10)	0.2452 (4)	0.9302 (5)	0.045 (2)
C14	0.3902 (10)	0.3114 (4)	0.9432 (6)	0.048 (3)
H14	0.3449	0.3234	0.9875	0.057*
C15	0.4267 (9)	0.3604 (4)	0.8902 (6)	0.043 (2)
C16	0.4953 (10)	0.3435 (4)	0.8254 (6)	0.047 (2)
H16	0.5216	0.3766	0.7906	0.057*
C17	0.5928 (10)	0.2625 (5)	0.7395 (6)	0.052 (3)
H17	0.6081	0.2992	0.7066	0.062*
C18	0.6914 (11)	0.1982 (4)	0.6398 (6)	0.059 (3)
H18A	0.7973	0.2059	0.6502	0.071*
H18B	0.6442	0.2305	0.5987	0.071*
C19	0.6558 (11)	0.1265 (4)	0.6100 (6)	0.056 (3)
H19A	0.5510	0.1226	0.5872	0.067*
H19B	0.7103	0.1153	0.5664	0.067*
C20	0.8556 (10)	0.0652 (5)	0.6983 (6)	0.061 (3)
H20A	0.8725	0.0239	0.7293	0.091*
H20B	0.9068	0.1014	0.7305	0.091*
H20C	0.8914	0.0607	0.6469	0.091*
C21	0.7334 (10)	−0.0092 (5)	0.8631 (6)	0.044 (2)
C22	0.8217 (10)	−0.0497 (5)	0.1533 (6)	0.071 (3)
H22A	0.8432	−0.0657	0.1013	0.107*
H22B	0.8283	−0.0865	0.1921	0.107*
H22C	0.8917	−0.0154	0.1755	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0465 (8)	0.0318 (6)	0.0374 (7)	0.0009 (5)	0.0140 (6)	0.0000 (5)
Ni2	0.0449 (7)	0.0264 (6)	0.0357 (7)	0.0005 (5)	0.0140 (6)	−0.0007 (5)
Br1	0.0776 (8)	0.0362 (6)	0.0944 (9)	0.0020 (5)	0.0229 (7)	−0.0143 (6)
Br2	0.0783 (8)	0.0426 (6)	0.0560 (7)	−0.0078 (5)	0.0329 (6)	−0.0048 (5)
Br3	0.0927 (9)	0.0551 (7)	0.0637 (7)	0.0114 (6)	0.0426 (7)	0.0071 (6)
Br4	0.0686 (8)	0.0395 (6)	0.0873 (9)	0.0079 (5)	0.0202 (7)	−0.0125 (6)
S1	0.101 (2)	0.0635 (19)	0.069 (2)	0.0369 (18)	0.0174 (19)	0.0090 (16)
S2	0.088 (2)	0.068 (2)	0.106 (3)	0.0307 (18)	0.034 (2)	0.0328 (19)
O1	0.056 (4)	0.031 (3)	0.048 (4)	−0.004 (3)	0.017 (3)	−0.003 (3)
O2	0.063 (4)	0.037 (4)	0.046 (4)	0.005 (3)	0.023 (3)	0.001 (3)
N1	0.059 (5)	0.036 (4)	0.043 (5)	0.003 (4)	0.015 (4)	−0.001 (4)
N2	0.051 (5)	0.047 (5)	0.053 (5)	0.008 (4)	0.014 (4)	−0.003 (4)
N3	0.053 (6)	0.034 (4)	0.058 (6)	0.003 (4)	0.009 (4)	−0.006 (4)
N4	0.066 (6)	0.032 (4)	0.050 (5)	−0.007 (4)	0.027 (4)	0.001 (4)
N5	0.052 (5)	0.043 (5)	0.043 (5)	−0.003 (4)	0.018 (4)	−0.002 (4)
N6	0.064 (6)	0.038 (5)	0.044 (5)	0.003 (4)	0.012 (4)	0.008 (4)
C1	0.047 (6)	0.035 (5)	0.041 (6)	−0.004 (4)	0.006 (5)	−0.005 (4)
C2	0.045 (6)	0.042 (6)	0.032 (6)	−0.002 (5)	−0.003 (5)	0.001 (4)
C3	0.048 (6)	0.029 (5)	0.043 (6)	−0.007 (4)	0.009 (5)	0.005 (4)
C4	0.048 (6)	0.043 (6)	0.049 (6)	0.005 (5)	0.008 (5)	−0.006 (5)
C5	0.051 (6)	0.029 (5)	0.052 (7)	0.014 (5)	−0.001 (5)	0.005 (5)
C6	0.052 (7)	0.038 (6)	0.064 (7)	−0.007 (5)	0.004 (6)	0.002 (5)
C7	0.056 (7)	0.039 (6)	0.048 (7)	−0.001 (5)	0.010 (5)	0.002 (5)
C8	0.073 (8)	0.055 (6)	0.049 (7)	−0.002 (5)	0.031 (6)	0.008 (5)
C9	0.077 (8)	0.058 (7)	0.047 (7)	−0.006 (6)	0.015 (6)	0.008 (6)
C10	0.040 (6)	0.053 (6)	0.043 (6)	−0.009 (5)	0.012 (5)	−0.007 (5)
C11	0.038 (6)	0.033 (5)	0.052 (6)	−0.004 (4)	0.007 (5)	−0.011 (5)
C12	0.040 (6)	0.034 (5)	0.035 (6)	−0.008 (4)	−0.001 (5)	0.000 (4)
C13	0.054 (6)	0.046 (6)	0.036 (6)	0.007 (5)	0.014 (5)	0.003 (4)
C14	0.065 (7)	0.038 (6)	0.044 (6)	0.001 (5)	0.019 (5)	−0.012 (5)
C15	0.033 (6)	0.039 (5)	0.057 (7)	0.006 (4)	0.009 (5)	−0.018 (5)
C16	0.056 (7)	0.032 (5)	0.052 (7)	0.000 (5)	0.007 (5)	0.005 (5)
C17	0.072 (7)	0.040 (6)	0.046 (6)	0.001 (5)	0.017 (6)	0.012 (5)
C18	0.086 (8)	0.044 (6)	0.055 (7)	−0.007 (5)	0.032 (6)	−0.003 (5)
C19	0.069 (7)	0.045 (6)	0.059 (7)	−0.006 (5)	0.025 (6)	0.003 (5)
C20	0.055 (7)	0.063 (7)	0.070 (8)	−0.003 (6)	0.025 (6)	−0.017 (6)
C21	0.046 (6)	0.046 (6)	0.039 (6)	−0.008 (5)	0.010 (5)	0.005 (5)
C22	0.056 (7)	0.078 (8)	0.089 (9)	0.018 (6)	0.040 (7)	0.002 (7)

Geometric parameters (Å, º) top

Ni1—O1	1.911 (6)	C2—C3	1.428 (11)
Ni1—N1	1.934 (7)	C3—C4	1.388 (11)
Ni1—N2	2.019 (7)	C4—C5	1.370 (11)
Ni1—N3	1.973 (8)	C4—H4	0.9300
Ni1—N6ⁱ	2.643 (8)	C5—C6	1.365 (12)
Ni2—O2	1.904 (5)	C6—H6	0.9300
Ni2—N3ⁱ	2.589 (8)	C7—H7	0.9300
Ni2—N4	1.935 (7)	C8—C9	1.532 (12)
Ni2—N6	1.978 (7)	C8—H8A	0.9700
Ni2—N5	2.010 (7)	C8—H8B	0.9700
Br1—C5	1.907 (8)	C9—H9A	0.9700
Br2—C3	1.888 (8)	C9—H9B	0.9700
Br3—C13	1.889 (9)	C11—C12	1.404 (11)
Br4—C15	1.902 (8)	C11—C16	1.410 (11)
S1—C10	1.602 (10)	C11—C17	1.460 (12)
S2—C21	1.617 (10)	C12—C13	1.412 (11)
O1—C2	1.299 (9)	C13—C14	1.369 (11)
O2—C12	1.301 (9)	C14—C15	1.383 (11)
N1—C7	1.270 (10)	C14—H14	0.9300
N1—C8	1.466 (10)	C15—C16	1.372 (11)
N2—C22	1.481 (10)	C16—H16	0.9300
N2—C9	1.509 (10)	C17—H17	0.9300
N2—H2A	0.9100	C18—C19	1.519 (11)
N3—C10	1.166 (10)	C18—H18A	0.9700
N4—C17	1.283 (10)	C18—H18B	0.9700
N4—C18	1.481 (10)	C19—H19A	0.9700
N5—C19	1.462 (10)	C19—H19B	0.9700
N5—C20	1.472 (10)	C20—H20A	0.9600
N5—H5A	0.9100	C20—H20B	0.9600
N6—C21	1.161 (10)	C20—H20C	0.9600
C1—C6	1.403 (11)	C22—H22A	0.9600
C1—C2	1.412 (11)	C22—H22B	0.9600
C1—C7	1.457 (11)	C22—H22C	0.9600

O1—Ni1—N1	93.3 (3)	N1—C7—H7	116.8
O1—Ni1—N3	93.2 (3)	C1—C7—H7	116.8
N1—Ni1—N3	160.5 (3)	N1—C8—C9	105.8 (7)
O1—Ni1—N2	166.4 (3)	N1—C8—H8A	110.6
N1—Ni1—N2	84.4 (3)	C9—C8—H8A	110.6
N3—Ni1—N2	93.3 (3)	N1—C8—H8B	110.6
O1—Ni1—N6ⁱ	86.9 (3)	C9—C8—H8B	110.6
N1—Ni1—N6ⁱ	109.2 (3)	H8A—C8—H8B	108.7
N2—Ni1—N6ⁱ	81.3 (3)	N2—C9—C8	106.5 (8)
N3—Ni1—N6ⁱ	89.5 (3)	N2—C9—H9A	110.4
O2—Ni2—N4	93.9 (3)	C8—C9—H9A	110.4
O2—Ni2—N6	92.2 (3)	N2—C9—H9B	110.4
N4—Ni2—N6	166.8 (3)	C8—C9—H9B	110.4
O2—Ni2—N5	172.3 (3)	H9A—C9—H9B	108.6
N4—Ni2—N5	83.6 (3)	N3—C10—S1	177.8 (9)
N6—Ni2—N5	91.8 (3)	C12—C11—C16	122.2 (8)
O2—Ni2—N3ⁱ	88.0 (3)	C12—C11—C17	123.5 (8)
N4—Ni2—N3ⁱ	101.0 (3)	C16—C11—C17	114.4 (8)
N5—Ni2—N3ⁱ	85.2 (3)	O2—C12—C11	124.9 (8)
N6—Ni2—N3ⁱ	91.0 (3)	O2—C12—C13	119.7 (8)
C2—O1—Ni1	127.1 (6)	C11—C12—C13	115.4 (8)
C12—O2—Ni2	127.0 (5)	C14—C13—C12	123.0 (8)
C7—N1—C8	120.3 (8)	C14—C13—Br3	118.6 (7)
C7—N1—Ni1	125.8 (6)	C12—C13—Br3	118.4 (6)
C8—N1—Ni1	113.8 (6)	C13—C14—C15	119.7 (8)
C22—N2—C9	112.5 (7)	C13—C14—H14	120.1
C22—N2—Ni1	115.6 (6)	C15—C14—H14	120.1
C9—N2—Ni1	106.6 (5)	C16—C15—C14	120.7 (8)
C22—N2—H2A	107.2	C16—C15—Br4	120.4 (7)
C9—N2—H2A	107.2	C14—C15—Br4	118.9 (6)
Ni1—N2—H2A	107.2	C15—C16—C11	119.0 (8)
C10—N3—Ni1	152.4 (7)	C15—C16—H16	120.5
C17—N4—C18	118.3 (7)	C11—C16—H16	120.5
C17—N4—Ni2	126.4 (6)	N4—C17—C11	124.1 (8)
C18—N4—Ni2	115.2 (6)	N4—C17—H17	117.9
C19—N5—C20	112.4 (7)	C11—C17—H17	117.9
C19—N5—Ni2	106.6 (5)	N4—C18—C19	104.9 (7)
C20—N5—Ni2	114.1 (6)	N4—C18—H18A	110.8
C19—N5—H5A	107.9	C19—C18—H18A	110.8
C20—N5—H5A	107.9	N4—C18—H18B	110.8
Ni2—N5—H5A	107.9	C19—C18—H18B	110.8
C21—N6—Ni2	147.6 (7)	H18A—C18—H18B	108.9
C6—C1—C2	122.1 (8)	N5—C19—C18	109.5 (8)
C6—C1—C7	116.5 (8)	N5—C19—H19A	109.8
C2—C1—C7	121.4 (8)	C18—C19—H19A	109.8
O1—C2—C1	125.3 (8)	N5—C19—H19B	109.8
O1—C2—C3	119.8 (8)	C18—C19—H19B	109.8
C1—C2—C3	115.0 (8)	H19A—C19—H19B	108.2
C4—C3—C2	122.7 (8)	N5—C20—H20A	109.5
C4—C3—Br2	118.6 (7)	N5—C20—H20B	109.5
C2—C3—Br2	118.7 (6)	H20A—C20—H20B	109.5
C5—C4—C3	119.1 (8)	N5—C20—H20C	109.5
C5—C4—H4	120.4	H20A—C20—H20C	109.5
C3—C4—H4	120.4	H20B—C20—H20C	109.5
C6—C5—C4	121.6 (8)	N6—C21—S2	178.9 (9)
C6—C5—Br1	120.1 (7)	N2—C22—H22A	109.5
C4—C5—Br1	118.3 (7)	N2—C22—H22B	109.5
C5—C6—C1	119.5 (9)	H22A—C22—H22B	109.5
C5—C6—H6	120.2	N2—C22—H22C	109.5
C1—C6—H6	120.2	H22A—C22—H22C	109.5
N1—C7—C1	126.3 (8)	H22B—C22—H22C	109.5

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.91	2.48	3.269 (9)	146
N5—H5A···O1ⁱ	0.91	2.15	3.012 (9)	158
N5—H5A···Br2ⁱ	0.91	2.86	3.500 (7)	129

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₁₀H₁₁Br₂N₂O)₂(NCS)₂]
M_r	451.82
Crystal system, space group	Monoclinic, P21/n
Temperature (K)	293
a, b, c (Å)	9.2040 (18), 19.833 (4), 16.319 (3)
β (°)	100.71 (3)
V (Å³)	2927.0 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	6.92
Crystal size (mm)	0.43 × 0.40 × 0.38

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.155, 0.178
No. of measured, independent and observed [I > 2σ(I)] reflections	25095, 6938, 2858
R_int	0.139
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.151, 0.94
No. of reflections	6938
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.77

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.91	2.48	3.269 (9)	145.5
N5—H5A···O1ⁱ	0.91	2.15	3.012 (9)	158.3
N5—H5A···Br2ⁱ	0.91	2.86	3.500 (7)	128.5

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The author acknowledges Huaihua University for a research grant.

References

Arıcı, C., Yüzer, D., Atakol, O., Fuess, H. & Svoboda, I. (2005). Acta Cryst. E61, m919–m921. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SMART (Version 5.625), SAINT (Version 6.01). SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hebbachi, R. & Benali-Cherif, N. (2005). Acta Cryst. E61, m1188–m1190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Henkel, G. & Krebs, B. (2004). Chem. Rev. 104, 801–824. Web of Science CrossRef PubMed CAS Google Scholar
Salmon, L., Thuéry, P. & Ephritikhine, M. (2005). Acta Cryst. E61, m2607–m2609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sarı, M., Atakol, O., Svoboda, I. & Fuess, H. (2006). Acta Cryst. E62, m563–m565. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 64| Part 2| February 2008| Page m295

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