catena-Poly[[bis­(2-amino­ethane­sulfon­ato-κ2N,O)nickel(II)]-μ-1,4-bis­(1H-imid­azol-1-yl)benzene-κ2N3:N3′]

Liu, J.-B.

doi:10.1107/S1600536811009238

metal-organic compounds

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Volume 67| Part 4| April 2011| Page m452

doi:10.1107/S1600536811009238

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catena-Poly[[bis(2-aminoethanesulfonato-κ²N,O)nickel(II)]-μ-1,4-bis(1H-imidazol-1-yl)benzene-κ²N³:N^3′]

Jin-Biao Liu ^a ^*

^aChemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, People's Republic of China
^*Correspondence e-mail: liujinbiao07@126.com

(Received 18 February 2011; accepted 10 March 2011; online 15 March 2011)

In the hydrothermally prepared title coordination polymer, [Ni(C₂H₆NO₃S)₂(C₁₂H₁₀N₄)]_n, the Ni^II ion and the 1,4-bis(1H-imidazol-1-yl)benzene ligand occupy special positions on inversion centers. The metal ion shows a slightly distorted octahedral coordination geometry, being linked to two N atoms of two 1,4-bis(imidazol-1-yl)benzene ligands and to two O and two N atoms of two chelating 2-aminoethanesulfonate ligands. The 1,4-bis(imidazol-1-yl)benzene ligands bridge symmetry-related Ni^II ions forming polymeric chains along the [110] direction.

Related literature

For some examples of transition metal complexes of 2-aminoethanesulfonic acid (taurine), see: Cai et al. (2004 , 2006 ); Jiang et al. (2006 , 2005 ).

Experimental

Crystal data

[Ni(C₂H₆NO₃S)₂(C₁₂H₁₀N₄)]
M_r = 517.23
Monoclinic, P 2₁ /c
a = 7.4559 (15) Å
b = 11.494 (2) Å
c = 12.481 (3) Å
β = 96.19 (3)°
V = 1063.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 295 K
0.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.841, T_max = 0.891
10967 measured reflections
2426 independent reflections
1974 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.097
S = 1.14
2426 reflections
142 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Ni1	2.079 (2)
Ni1—O1	2.1070 (18)
Ni1—N2	2.126 (2)

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 global, I. DOI: 10.1107/S1600536811009238/gk2349sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009238/gk2349Isup2.hkl

checkCIF report

Comment top

Taurine, an amino acid containing sulfur, has important physiological functions. In fact, taurine is one of the most abundant free amino-acid-like compounds found in the heart, the skeletal muscles and the nervous system. As part of our research on taurine complexes we report here the synthesis and crystal structure of the title nikel(II) complex with taurine and 1,4-bis(imidazol-1-yl)benzene.

The crystal structure shows that two taurine anions chelate to the Ni^II ion via terminal N and O atoms. In addition the Ni^II ion is coordinated to two bridging 1,4-bis(imidazol-1-yl)benzene ligands to form one-dimensional polymer. The Ni^IIion and 1,4-bis(imidazol-1-yl)benzene ligand are located on inversion center. The coordination environment around nickel(II) is shown in Fig. 1. The Ni^II atom is six-coordinated in a distorted octahedral geometry. N-H···O and C-H···O hydrogen bonds assemble the coordination polymers into a three-dimensional supramolecular network (Fig. 2). One of the taurine N–H groups is not involved in hydrogen bonding.

Related literature top

For some examples of transition metal complexes of 2-aminoethanesulfonic acid (taurine), see: Cai et al. (2004, 2006); Jiang et al. (2006, 2005).

Experimental top

Reagents and solvents used were of commercially available quality. A water solution (10 ml) of 2-aminoethanesulfonic acid (2.0 mmol) and KOH(2.0 mmol) was mixed with water solution (10 ml) of Ni(NO₃)₂.2H₂O (1.0 mmol). 1,4-Bis(imidazol-1-yl)benzene (1 mmol) was added to the mixture, then dropped into a 23 ml Teflon-stainless steel reactor and heated at 423 K for 4 d. After cooling to room temperature, single crystals of the title compound were obtained (yield 30%). Analysis found (%): C37.27, H 4.36, N 16.32; calculated (%): C 37.14, H 4.19, N 16.24, IR (KBr, cm^-1): 1031, 1166, 1233 (–SO₃), 3256.6, 3300.8 (N—H).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SMART (Bruker, 2007); data reduction: SAINT (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. The structure of the title compound with displacement ellipsoids shown at the 30% probability level. Symmetry code for the atoms with the B label: 2-x, -y, 2-z.
	Fig. 2. The crystal packing viewed down the a axis. Hydrogen bonds and short contacts are shown with dashed lines.

catena-Poly[[bis(2-aminoethanesulfonato- κ²N,O)nickel(II)]-µ-1,4-bis(1H-imidazol-1- yl)benzene-κ²N³:N^3'] top

Crystal data top

[Ni(C₂H₆NO₃S)₂(C₁₂H₁₀N₄)]	F(000) = 536
M_r = 517.23	D_x = 1.615 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9767 reflections
a = 7.4559 (15) Å	θ = 3.0–27.5°
b = 11.494 (2) Å	µ = 1.16 mm⁻¹
c = 12.481 (3) Å	T = 295 K
β = 96.19 (3)°	Block, blue
V = 1063.4 (4) Å³	0.15 × 0.13 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	2426 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.841, T_max = 0.891	k = −14→14
10967 measured reflections	l = −16→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0348P)² + 0.7272P] where P = (F_o² + 2F_c²)/3
2426 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ni(C₂H₆NO₃S)₂(C₁₂H₁₀N₄)]	V = 1063.4 (4) Å³
M_r = 517.23	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4559 (15) Å	µ = 1.16 mm⁻¹
b = 11.494 (2) Å	T = 295 K
c = 12.481 (3) Å	0.15 × 0.13 × 0.10 mm
β = 96.19 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2426 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1974 reflections with I > 2σ(I)
T_min = 0.841, T_max = 0.891	R_int = 0.056
10967 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.14	Δρ_max = 0.28 e Å⁻³
2426 reflections	Δρ_min = −0.47 e Å⁻³
142 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
N1	0.8455 (3)	−0.0438 (2)	0.85704 (19)	0.0309 (6)
H1A	0.8967	−0.1070	0.8304	0.037*
H1B	0.7365	−0.0661	0.8744	0.037*
C1	0.8139 (5)	0.0411 (3)	0.7680 (3)	0.0441 (9)
H1C	0.7468	0.1069	0.7916	0.053*
H1D	0.7420	0.0050	0.7076	0.053*
Ni1	1.0000	0.0000	1.0000	0.01926 (15)
S1	1.10651 (11)	0.18961 (6)	0.81832 (6)	0.0343 (2)
N2	0.7881 (3)	0.11099 (19)	1.03850 (19)	0.0270 (5)
O1	1.1241 (3)	0.14000 (16)	0.92774 (15)	0.0286 (5)
N3	0.6253 (3)	0.27144 (19)	1.04500 (18)	0.0252 (5)
C7	0.5608 (4)	0.3874 (2)	1.0207 (2)	0.0233 (6)
O3	0.9938 (3)	0.29267 (19)	0.8110 (2)	0.0523 (7)
O2	1.2806 (3)	0.2066 (2)	0.7786 (2)	0.0556 (7)
C3	0.7630 (4)	0.2182 (2)	1.0020 (2)	0.0310 (7)
H3	0.8314	0.2529	0.9527	0.037*
C5	0.6610 (4)	0.0958 (3)	1.1103 (3)	0.0363 (8)
H5	0.6455	0.0278	1.1486	0.044*
C4	0.5626 (4)	0.1936 (3)	1.1170 (3)	0.0352 (8)
H4	0.4714	0.2061	1.1609	0.042*
C6	0.6539 (5)	0.4610 (3)	0.9619 (3)	0.0551 (11)
H6	0.7584	0.4353	0.9349	0.066*
C2	0.9901 (5)	0.0834 (3)	0.7320 (3)	0.0456 (9)
H2A	0.9659	0.1163	0.6604	0.055*
H2B	1.0690	0.0169	0.7270	0.055*
C8	0.4054 (5)	0.4257 (3)	1.0584 (3)	0.0551 (11)
H8	0.3393	0.3757	1.0977	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0350 (14)	0.0287 (13)	0.0289 (14)	−0.0018 (11)	0.0032 (11)	−0.0013 (11)
C1	0.051 (2)	0.046 (2)	0.0330 (19)	0.0049 (17)	−0.0058 (16)	0.0065 (15)
Ni1	0.0240 (3)	0.0133 (2)	0.0217 (3)	0.0050 (2)	0.00797 (19)	0.00226 (19)
S1	0.0476 (5)	0.0250 (4)	0.0340 (4)	0.0060 (3)	0.0211 (4)	0.0105 (3)
N2	0.0303 (13)	0.0198 (12)	0.0326 (14)	0.0079 (10)	0.0114 (11)	0.0040 (10)
O1	0.0359 (12)	0.0209 (10)	0.0307 (11)	−0.0019 (9)	0.0104 (9)	0.0061 (8)
N3	0.0255 (13)	0.0181 (12)	0.0339 (13)	0.0077 (10)	0.0114 (11)	0.0028 (10)
C7	0.0245 (14)	0.0172 (13)	0.0289 (15)	0.0076 (11)	0.0061 (12)	0.0001 (11)
O3	0.0687 (18)	0.0327 (13)	0.0596 (16)	0.0189 (12)	0.0253 (13)	0.0237 (11)
O2	0.0602 (17)	0.0518 (16)	0.0625 (17)	−0.0040 (12)	0.0420 (14)	0.0083 (13)
C3	0.0374 (17)	0.0217 (15)	0.0375 (17)	0.0116 (12)	0.0199 (14)	0.0063 (12)
C5	0.0379 (18)	0.0232 (16)	0.051 (2)	0.0074 (13)	0.0217 (16)	0.0092 (14)
C4	0.0314 (17)	0.0276 (16)	0.050 (2)	0.0064 (13)	0.0205 (15)	0.0082 (14)
C6	0.050 (2)	0.0357 (18)	0.088 (3)	0.0263 (17)	0.050 (2)	0.0252 (19)
C2	0.070 (3)	0.044 (2)	0.0235 (17)	0.0024 (18)	0.0096 (16)	0.0078 (14)
C8	0.052 (2)	0.0331 (19)	0.089 (3)	0.0228 (17)	0.048 (2)	0.0285 (19)

Geometric parameters (Å, º) top

N1—C1	1.479 (4)	N3—C3	1.355 (3)
N1—Ni1	2.079 (2)	N3—C4	1.384 (4)
N1—H1A	0.9000	N3—C7	1.438 (3)
N1—H1B	0.9000	C7—C6	1.359 (4)
C1—C2	1.513 (5)	C7—C8	1.369 (4)
C1—H1C	0.9700	C3—H3	0.9300
C1—H1D	0.9700	C5—C4	1.349 (4)
Ni1—O1	2.1070 (18)	C5—H5	0.9300
Ni1—N2	2.126 (2)	C4—H4	0.9300
S1—O3	1.450 (2)	C6—H6	0.9300
S1—O2	1.452 (2)	C2—H2A	0.9700
S1—O1	1.473 (2)	C2—H2B	0.9700
S1—C2	1.790 (4)	C8—C6ⁱ	1.390 (4)
N2—C3	1.320 (3)	C8—H8	0.9300
N2—C5	1.384 (4)

C1—N1—Ni1	120.9 (2)	O1—S1—C2	106.43 (13)
C1—N1—H1A	107.1	C3—N2—C5	105.1 (2)
Ni1—N1—H1A	107.1	C3—N2—Ni1	124.28 (19)
C1—N1—H1B	107.1	C5—N2—Ni1	130.42 (18)
Ni1—N1—H1B	107.1	S1—O1—Ni1	133.89 (13)
H1A—N1—H1B	106.8	C3—N3—C4	106.8 (2)
N1—C1—C2	111.2 (3)	C3—N3—C7	125.9 (2)
N1—C1—H1C	109.4	C4—N3—C7	127.4 (2)
C2—C1—H1C	109.4	C6—C7—C8	119.1 (3)
N1—C1—H1D	109.4	C6—C7—N3	120.8 (2)
C2—C1—H1D	109.4	C8—C7—N3	120.1 (3)
H1C—C1—H1D	108.0	N2—C3—N3	111.7 (2)
N1ⁱⁱ—Ni1—N1	180.0	N2—C3—H3	124.1
N1ⁱⁱ—Ni1—O1ⁱⁱ	92.64 (9)	N3—C3—H3	124.1
N1—Ni1—O1ⁱⁱ	87.36 (9)	C4—C5—N2	110.5 (3)
N1ⁱⁱ—Ni1—O1	87.36 (9)	C4—C5—H5	124.8
N1—Ni1—O1	92.64 (9)	N2—C5—H5	124.8
O1ⁱⁱ—Ni1—O1	180.0	C5—C4—N3	105.9 (3)
N1ⁱⁱ—Ni1—N2ⁱⁱ	89.01 (10)	C5—C4—H4	127.0
N1—Ni1—N2ⁱⁱ	90.99 (10)	N3—C4—H4	127.0
O1ⁱⁱ—Ni1—N2ⁱⁱ	90.57 (8)	C7—C6—C8ⁱ	120.8 (3)
O1—Ni1—N2ⁱⁱ	89.43 (8)	C7—C6—H6	119.6
N1ⁱⁱ—Ni1—N2	90.99 (10)	C8ⁱ—C6—H6	119.6
N1—Ni1—N2	89.01 (10)	C1—C2—S1	114.9 (2)
O1ⁱⁱ—Ni1—N2	89.43 (8)	C1—C2—H2A	108.5
O1—Ni1—N2	90.57 (8)	S1—C2—H2A	108.5
N2ⁱⁱ—Ni1—N2	180.000 (1)	C1—C2—H2B	108.5
O3—S1—O2	113.74 (15)	S1—C2—H2B	108.5
O3—S1—O1	111.58 (13)	H2A—C2—H2B	107.5
O2—S1—O1	112.03 (14)	C7—C8—C6ⁱ	120.1 (3)
O3—S1—C2	106.22 (17)	C7—C8—H8	119.9
O2—S1—C2	106.24 (16)	C6ⁱ—C8—H8	119.9

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1a···O3ⁱⁱⁱ	0.90	2.33	3.148 (3)	151
C3—H3···O1	0.93	2.59	3.075 (4)	113
C3—H3···O3	0.93	2.29	3.203 (4)	165
C4—H4···O2^iv	0.93	2.37	3.274 (4)	163
C8—H8···O2^iv	0.93	2.53	3.359 (4)	149

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂H₆NO₃S)₂(C₁₂H₁₀N₄)]
M_r	517.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.4559 (15), 11.494 (2), 12.481 (3)
β (°)	96.19 (3)
V (Å³)	1063.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.15 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.841, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	10967, 2426, 1974
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.097, 1.14
No. of reflections	2426
No. of parameters	142
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.47

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

Selected bond lengths (Å) top

N1—Ni1	2.079 (2)	Ni1—N2	2.126 (2)
Ni1—O1	2.1070 (18)

Acknowledgements

This work was supported by the Natural Science Foundation of Tian Jin.

References

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