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Acta Cryst. (2007). E63, m1974    [ doi:10.1107/S1600536807029911 ]

Bis[2-(2-pyridylmethylamino)ethanesulfonato-[kappa]3N,N',O]nickel(II)

B.-L. Liao, J.-X. Li and Y.-M. Jiang

Abstract top

In mononuclear [Ni(C8H11N2O3S)2], a nickel(II) complex of 2-(2-pyridylmethylamino)ethanesulfonic acid, the six-coordinate Ni atom lies on a centre of symmetry. The monodeprotonated anion coordinates in a facial arrangement through two N and one O atoms. Intermolecular N-H...O hydrogen bonds are present in the crystal structure.

Comment top

The compound is isostructural with [Co(C8H11N2O3S)2], whose structure has been described in detail (Li et al., 2006)·The six-coordiante nickel atom lies on an inversion centre with the two monodeprotonated lingds coordinate in a tridentate facial arrangement with its three donor atoms.

The N—H donor and S═O acceptor groups of the PMT ligand participate in the hydrogen bonding and form a two-dimensional network in the bc plane (Fig. 2 and Table 2).

Related literature top

For the isostuctural cobalt(II) analog, see: Li et al. (2006).

Experimental top

2-(2-Pyridylmethylamino)ethanesulfonic acid was prepared according to the method of Li et al., 2006). The ligand (2.0 mmol, 0.432 g) was dissolved in water (15 ml). To this solution, NiCl26H2O (1.0 m mol, 0.238 g) was added, and the resulting mixture was stirred at 323 K for 6 h. The solution was filtered; the filtrate was left to stand at room temperature. Green block-shaped crystals were obtained in a yield of 43%. Analysis, found(%): C 39.31; H 4.54; N 11.38; S 13.01. C16H22NiN4O6S2 requires(%): C 39.25; H 4.50; N 11.45; S 13.08. IR(KBr, ν cm−1):771.3[γ(C═C—H)], 746.5(γ CH2); 1189.5, 1149.5, 1035.1(ν SO3−); 1608.7, 1571.8 (ν C═ C+C═N); 3213.8 (νN-H).

Refinement top

H atoms bonded to C were positioned geometrically with C—H distance 0.93–0.97 Å, and treated as riding atoms, with Uiso(H)=1.2Ueq(C). The N—H hydrogen atom was located in a difference Fourier map and refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Symmetry code:(i)-x, −y, −z.
[Figure 2] Fig. 2. Packing of (I), showing the two-dimensional sheet structure in the bc plane, linked via hydrogen bonds (dashed lines). H atoms bonded to C atoms have been omitted.
Bis[2-(2-pyridylmethylamino)ethanesulfonato- κ3N,N',O]nickel(II) top
Crystal data top
[Ni(C8H11N2O3S)2]F000 = 508
Mr = 489.21Dx = 1.554 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5566 reflections
a = 9.6090 (10) Åθ = 2.8–28.2º
b = 9.9270 (10) ŵ = 1.17 mm−1
c = 11.4537 (12) ÅT = 291 (2) K
β = 106.8480 (10)ºBlock, green
V = 1045.66 (19) Å30.35 × 0.26 × 0.22 mm
Z = 2
Data collection top
Bruker APEX II CCD area-detector
diffractometer		2401 independent reflections
Radiation source: fine-focus sealed tube2212 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.016
T = 291(2) Kθmax = 27.5º
φ and ω scansθmin = 2.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.683, Tmax = 0.787k = −12→12
8966 measured reflectionsl = −14→14
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.068  w = 1/[σ2(Fo2) + (0.04P)2 + 0.3431P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2401 reflectionsΔρmax = 0.30 e Å−3
137 parametersΔρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ni(C8H11N2O3S)2]V = 1045.66 (19) Å3
Mr = 489.21Z = 2
Monoclinic, P21/cMo Kα
a = 9.6090 (10) ŵ = 1.17 mm−1
b = 9.9270 (10) ÅT = 291 (2) K
c = 11.4537 (12) Å0.35 × 0.26 × 0.22 mm
β = 106.8480 (10)º
Data collection top
Bruker APEX II CCD area-detector
diffractometer		2401 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2212 reflections with I > 2σ(I)
Tmin = 0.683, Tmax = 0.787Rint = 0.016
8966 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024137 parameters
wR(F2) = 0.068H atoms treated by a mixture of
independent and constrained refinement
S = 1.04Δρmax = 0.30 e Å−3
2401 reflectionsΔρmin = −0.38 e Å−3
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
xyzUiso*/Ueq
Ni10.00000.00000.00000.02225 (9)
S1−0.13109 (4)0.28994 (4)0.04303 (3)0.02938 (10)
O1−0.05360 (16)0.39933 (12)0.11905 (10)0.0458 (3)
O2−0.28622 (14)0.29309 (16)0.02363 (14)0.0588 (4)
O3−0.06507 (13)0.15954 (11)0.09085 (10)0.0356 (2)
N10.21837 (14)0.03407 (13)0.10617 (12)0.0303 (3)
N20.07293 (13)0.13004 (12)−0.11590 (11)0.0278 (2)
C10.30118 (16)0.08851 (16)0.04133 (16)0.0361 (3)
C20.4419 (2)0.1324 (2)0.0964 (2)0.0603 (6)
H20.49700.17060.05030.072*
C30.4988 (2)0.1182 (3)0.2214 (2)0.0772 (8)
H30.59290.14730.26030.093*
C40.4153 (2)0.0608 (3)0.2882 (2)0.0639 (6)
H40.45250.04980.37210.077*
C50.2757 (2)0.01988 (18)0.22770 (16)0.0405 (4)
H50.2192−0.01880.27240.049*
C60.22948 (17)0.09836 (17)−0.09381 (15)0.0371 (3)
H6A0.27570.1685−0.12840.045*
H6B0.23990.0137−0.13280.045*
C70.05421 (17)0.27742 (14)−0.10031 (14)0.0316 (3)
H7A0.07860.3259−0.16530.038*
H7B0.12060.3065−0.02340.038*
C8−0.10033 (17)0.31163 (15)−0.10230 (13)0.0303 (3)
H8A−0.16720.2546−0.16150.036*
H8B−0.12070.4044−0.12820.036*
H1N0.0333 (19)0.1125 (17)−0.1905 (17)0.033 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02352 (14)0.02147 (14)0.02214 (13)−0.00247 (8)0.00720 (10)0.00056 (8)
S10.0344 (2)0.02661 (18)0.02887 (18)0.00052 (13)0.01194 (14)−0.00103 (13)
O10.0754 (9)0.0310 (6)0.0330 (6)−0.0097 (6)0.0188 (6)−0.0074 (5)
O20.0368 (7)0.0803 (11)0.0640 (9)0.0074 (7)0.0221 (6)0.0116 (8)
O30.0550 (7)0.0273 (5)0.0282 (5)0.0044 (5)0.0179 (5)0.0016 (4)
N10.0269 (6)0.0304 (6)0.0321 (6)−0.0018 (5)0.0064 (5)−0.0012 (5)
N20.0321 (6)0.0272 (6)0.0253 (6)−0.0023 (5)0.0103 (5)0.0003 (5)
C10.0268 (7)0.0356 (8)0.0475 (9)−0.0008 (6)0.0129 (6)−0.0004 (7)
C20.0296 (9)0.0726 (14)0.0790 (15)−0.0126 (9)0.0163 (9)−0.0016 (12)
C30.0305 (10)0.107 (2)0.0793 (17)−0.0160 (11)−0.0067 (10)−0.0112 (15)
C40.0437 (11)0.0867 (16)0.0464 (11)0.0005 (11)−0.0106 (9)−0.0070 (11)
C50.0378 (9)0.0444 (9)0.0350 (8)0.0026 (7)0.0037 (7)−0.0020 (7)
C60.0350 (8)0.0394 (8)0.0444 (9)−0.0021 (6)0.0232 (7)0.0029 (7)
C70.0393 (8)0.0251 (7)0.0326 (7)−0.0047 (6)0.0140 (6)0.0025 (6)
C80.0373 (8)0.0274 (7)0.0247 (6)0.0020 (6)0.0065 (6)0.0028 (5)
Geometric parameters (Å, °) top
Ni1—O32.0879 (11)C1—C61.504 (2)
Ni1—O3i2.0879 (11)C2—C31.383 (3)
Ni1—N22.1116 (12)C2—H20.9300
Ni1—N2i2.1117 (12)C3—C41.382 (4)
Ni1—N1i2.1253 (13)C3—H30.9300
Ni1—N12.1253 (13)C4—C51.380 (3)
S1—O21.4424 (13)C4—H40.9300
S1—O11.4547 (12)C5—H50.9300
S1—O31.4753 (11)C6—H6A0.9700
S1—C81.7860 (15)C6—H6B0.9700
N1—C51.348 (2)C7—C81.517 (2)
N1—C11.349 (2)C7—H7A0.9700
N2—C61.4849 (19)C7—H7B0.9700
N2—C71.4911 (19)C8—H8A0.9700
N2—H1N0.847 (18)C8—H8B0.9700
C1—C21.387 (2)
O3—Ni1—O3i180.0N1—C1—C6115.17 (13)
O3—Ni1—N292.95 (4)C2—C1—C6122.92 (16)
O3i—Ni1—N287.05 (4)C3—C2—C1118.7 (2)
O3—Ni1—N2i87.05 (4)C3—C2—H2120.7
O3i—Ni1—N2i92.95 (4)C1—C2—H2120.7
N2—Ni1—N2i180.00 (6)C4—C3—C2119.74 (19)
O3—Ni1—N1i90.99 (5)C4—C3—H3120.1
O3i—Ni1—N1i89.01 (5)C2—C3—H3120.1
N2—Ni1—N1i100.96 (5)C5—C4—C3118.6 (2)
N2i—Ni1—N1i79.04 (5)C5—C4—H4120.7
O3—Ni1—N189.01 (5)C3—C4—H4120.7
O3i—Ni1—N190.99 (5)N1—C5—C4122.30 (19)
N2—Ni1—N179.04 (5)N1—C5—H5118.9
N2i—Ni1—N1100.96 (5)C4—C5—H5118.9
N1i—Ni1—N1180.0N2—C6—C1109.17 (12)
O2—S1—O1113.76 (9)N2—C6—H6A109.8
O2—S1—O3112.97 (8)C1—C6—H6A109.8
O1—S1—O3110.02 (7)N2—C6—H6B109.8
O2—S1—C8107.25 (8)C1—C6—H6B109.8
O1—S1—C8105.88 (7)H6A—C6—H6B108.3
O3—S1—C8106.40 (7)N2—C7—C8111.68 (12)
S1—O3—Ni1129.73 (6)N2—C7—H7A109.3
C5—N1—C1118.73 (14)C8—C7—H7A109.3
C5—N1—Ni1127.92 (11)N2—C7—H7B109.3
C1—N1—Ni1113.01 (10)C8—C7—H7B109.3
C6—N2—C7109.81 (12)H7A—C7—H7B107.9
C6—N2—Ni1105.53 (9)C7—C8—S1112.62 (10)
C7—N2—Ni1116.81 (9)C7—C8—H8A109.1
C6—N2—H1N105.4 (12)S1—C8—H8A109.1
C7—N2—H1N106.7 (12)C7—C8—H8B109.1
Ni1—N2—H1N112.0 (12)S1—C8—H8B109.1
N1—C1—C2121.91 (17)H8A—C8—H8B107.8
O2—S1—O3—Ni1101.05 (11)N2i—Ni1—N2—C7160 (17)
O1—S1—O3—Ni1−130.63 (9)N1i—Ni1—N2—C790.36 (11)
C8—S1—O3—Ni1−16.37 (11)N1—Ni1—N2—C7−89.64 (11)
O3i—Ni1—O3—S1−153 (8)C5—N1—C1—C2−1.3 (3)
N2—Ni1—O3—S136.51 (10)Ni1—N1—C1—C2172.59 (15)
N2i—Ni1—O3—S1−143.49 (10)C5—N1—C1—C6179.00 (14)
N1i—Ni1—O3—S1−64.52 (10)Ni1—N1—C1—C6−7.13 (17)
N1—Ni1—O3—S1115.48 (10)N1—C1—C2—C30.7 (3)
O3—Ni1—N1—C565.02 (14)C6—C1—C2—C3−179.6 (2)
O3i—Ni1—N1—C5−114.98 (14)C1—C2—C3—C40.2 (4)
N2—Ni1—N1—C5158.22 (14)C2—C3—C4—C5−0.6 (4)
N2i—Ni1—N1—C5−21.78 (14)C1—N1—C5—C40.9 (3)
N1i—Ni1—N1—C576 (30)Ni1—N1—C5—C4−171.96 (16)
O3—Ni1—N1—C1−108.16 (11)C3—C4—C5—N10.0 (4)
O3i—Ni1—N1—C171.84 (11)C7—N2—C6—C181.22 (15)
N2—Ni1—N1—C1−14.97 (11)Ni1—N2—C6—C1−45.48 (14)
N2i—Ni1—N1—C1165.03 (11)N1—C1—C6—N236.05 (19)
N1i—Ni1—N1—C1−97 (30)C2—C1—C6—N2−143.67 (17)
O3—Ni1—N2—C6121.09 (10)C6—N2—C7—C8−171.05 (12)
O3i—Ni1—N2—C6−58.91 (10)Ni1—N2—C7—C8−50.99 (15)
N2i—Ni1—N2—C6−78 (17)N2—C7—C8—S183.95 (13)
N1i—Ni1—N2—C6−147.33 (9)O2—S1—C8—C7−166.32 (11)
N1—Ni1—N2—C632.67 (9)O1—S1—C8—C771.88 (12)
O3—Ni1—N2—C7−1.22 (10)O3—S1—C8—C7−45.17 (12)
O3i—Ni1—N2—C7178.78 (10)
Symmetry codes: (i) −x, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H1N···O1ii0.847 (18)2.100 (19)2.9394 (17)170.6 (16)
Symmetry codes: (ii) x, −y+1/2, z−1/2.
Table 1
Selected geometric parameters (Å) top
Ni1—O32.0879 (11)Ni1—N12.1253 (13)
Ni1—N22.1116 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H1N···O1i0.847 (18)2.100 (19)2.9394 (17)170.6 (16)
Symmetry codes: (i) x, −y+1/2, z−1/2.
Acknowledgements top

This work was funded by the Guangxi Science Foundation of the Guangxi Chuang Autonomous Region of the People's Republic of China (grant No. 0731053).

references
References top

Bruker (2004). APEX2 (Version 2004/1), SAINT ( Version 7.12a) and SHELXTL (Version 7.12a). Bruker AXS Inc., Madison, Wisconsin, USA.

Li, J.-X., Jiang, Y.-M. & Li, H.-Y. (2006). Acta Cryst. E62, m2984–m2986.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.