Bis[2-(2-pyridylmethyl­amino)­ethane­sulfonato-κ³N,N′,O]nickel(II)

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.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.068
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N1      ..       5.35 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N2      ..       7.10 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            O3  -NI1 -O3  -S1   -153.00  8.00   3.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N1  -NI1 -N1  -C5      8.00  0.00   3.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N1  -NI1 -N1  -C1     10.00  0.00   3.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            N2  -NI1 -N2  -C6    -78.00 17.00   3.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            N2  -NI1 -N2  -C7    160.00 17.00   3.555   1.555   1.555   1.555

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          R
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       1.91

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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).

S3. Refinement

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

Computing details

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

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Symmetry code:(i)-x, -y, -z.
	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)

Crystal data

[Ni(C8H11N2O3S)2]	F(000) = 508
Mr = 489.21	Dx = 1.554 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5566 reflections
a = 9.609 (1) Å	θ = 2.8–28.2°
b = 9.927 (1) Å	µ = 1.17 mm^−1
c = 11.4537 (12) Å	T = 291 K
β = 106.848 (1)°	Block, green
V = 1045.66 (19) Å^3	0.35 × 0.26 × 0.22 mm
Z = 2

Data collection

Bruker APEX II CCD area-detector diffractometer	2401 independent reflections
Radiation source: fine-focus sealed tube	2212 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.683, Tmax = 0.787	k = −12→12
8966 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 0.3431P] where P = (Fo^2 + 2Fc^2)/3
2401 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.0000	0.0000	0.0000	0.02225 (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)
N1	0.21837 (14)	0.03407 (13)	0.10617 (12)	0.0303 (3)
N2	0.07293 (13)	0.13004 (12)	−0.11590 (11)	0.0278 (2)
C1	0.30118 (16)	0.08851 (16)	0.04133 (16)	0.0361 (3)
C2	0.4419 (2)	0.1324 (2)	0.0964 (2)	0.0603 (6)
H2	0.4970	0.1706	0.0503	0.072*
C3	0.4988 (2)	0.1182 (3)	0.2214 (2)	0.0772 (8)
H3	0.5929	0.1473	0.2603	0.093*
C4	0.4153 (2)	0.0608 (3)	0.2882 (2)	0.0639 (6)
H4	0.4525	0.0498	0.3721	0.077*
C5	0.2757 (2)	0.01988 (18)	0.22770 (16)	0.0405 (4)
H5	0.2192	−0.0188	0.2724	0.049*
C6	0.22948 (17)	0.09836 (17)	−0.09381 (15)	0.0371 (3)
H6A	0.2757	0.1685	−0.1284	0.045*
H6B	0.2399	0.0137	−0.1328	0.045*
C7	0.05421 (17)	0.27742 (14)	−0.10031 (14)	0.0316 (3)
H7A	0.0786	0.3259	−0.1653	0.038*
H7B	0.1206	0.3065	−0.0234	0.038*
C8	−0.10033 (17)	0.31163 (15)	−0.10230 (13)	0.0303 (3)
H8A	−0.1672	0.2546	−0.1615	0.036*
H8B	−0.1207	0.4044	−0.1282	0.036*
H1N	0.0333 (19)	0.1125 (17)	−0.1905 (17)	0.033 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.02352 (14)	0.02147 (14)	0.02214 (13)	−0.00247 (8)	0.00720 (10)	0.00056 (8)
S1	0.0344 (2)	0.02661 (18)	0.02887 (18)	0.00052 (13)	0.01194 (14)	−0.00103 (13)
O1	0.0754 (9)	0.0310 (6)	0.0330 (6)	−0.0097 (6)	0.0188 (6)	−0.0074 (5)
O2	0.0368 (7)	0.0803 (11)	0.0640 (9)	0.0074 (7)	0.0221 (6)	0.0116 (8)
O3	0.0550 (7)	0.0273 (5)	0.0282 (5)	0.0044 (5)	0.0179 (5)	0.0016 (4)
N1	0.0269 (6)	0.0304 (6)	0.0321 (6)	−0.0018 (5)	0.0064 (5)	−0.0012 (5)
N2	0.0321 (6)	0.0272 (6)	0.0253 (6)	−0.0023 (5)	0.0103 (5)	0.0003 (5)
C1	0.0268 (7)	0.0356 (8)	0.0475 (9)	−0.0008 (6)	0.0129 (6)	−0.0004 (7)
C2	0.0296 (9)	0.0726 (14)	0.0790 (15)	−0.0126 (9)	0.0163 (9)	−0.0016 (12)
C3	0.0305 (10)	0.107 (2)	0.0793 (17)	−0.0160 (11)	−0.0067 (10)	−0.0112 (15)
C4	0.0437 (11)	0.0867 (16)	0.0464 (11)	0.0005 (11)	−0.0106 (9)	−0.0070 (11)
C5	0.0378 (9)	0.0444 (9)	0.0350 (8)	0.0026 (7)	0.0037 (7)	−0.0020 (7)
C6	0.0350 (8)	0.0394 (8)	0.0444 (9)	−0.0021 (6)	0.0232 (7)	0.0029 (7)
C7	0.0393 (8)	0.0251 (7)	0.0326 (7)	−0.0047 (6)	0.0140 (6)	0.0025 (6)
C8	0.0373 (8)	0.0274 (7)	0.0247 (6)	0.0020 (6)	0.0065 (6)	0.0028 (5)

Geometric parameters (Å, º)

Ni1—O3	2.0879 (11)	C1—C6	1.504 (2)
Ni1—O3^i	2.0879 (11)	C2—C3	1.383 (3)
Ni1—N2	2.1116 (12)	C2—H2	0.9300
Ni1—N2^i	2.1117 (12)	C3—C4	1.382 (4)
Ni1—N1^i	2.1253 (13)	C3—H3	0.9300
Ni1—N1	2.1253 (13)	C4—C5	1.380 (3)
S1—O2	1.4424 (13)	C4—H4	0.9300
S1—O1	1.4547 (12)	C5—H5	0.9300
S1—O3	1.4753 (11)	C6—H6A	0.9700
S1—C8	1.7860 (15)	C6—H6B	0.9700
N1—C5	1.348 (2)	C7—C8	1.517 (2)
N1—C1	1.349 (2)	C7—H7A	0.9700
N2—C6	1.4849 (19)	C7—H7B	0.9700
N2—C7	1.4911 (19)	C8—H8A	0.9700
N2—H1N	0.847 (18)	C8—H8B	0.9700
C1—C2	1.387 (2)
O3—Ni1—O3^i	180.0	N1—C1—C6	115.17 (13)
O3—Ni1—N2	92.95 (4)	C2—C1—C6	122.92 (16)
O3^i—Ni1—N2	87.05 (4)	C3—C2—C1	118.7 (2)
O3—Ni1—N2^i	87.05 (4)	C3—C2—H2	120.7
O3^i—Ni1—N2^i	92.95 (4)	C1—C2—H2	120.7
N2—Ni1—N2^i	180.00 (6)	C4—C3—C2	119.74 (19)
O3—Ni1—N1^i	90.99 (5)	C4—C3—H3	120.1
O3^i—Ni1—N1^i	89.01 (5)	C2—C3—H3	120.1
N2—Ni1—N1^i	100.96 (5)	C5—C4—C3	118.6 (2)
N2^i—Ni1—N1^i	79.04 (5)	C5—C4—H4	120.7
O3—Ni1—N1	89.01 (5)	C3—C4—H4	120.7
O3^i—Ni1—N1	90.99 (5)	N1—C5—C4	122.30 (19)
N2—Ni1—N1	79.04 (5)	N1—C5—H5	118.9
N2^i—Ni1—N1	100.96 (5)	C4—C5—H5	118.9
N1^i—Ni1—N1	180.0	N2—C6—C1	109.17 (12)
O2—S1—O1	113.76 (9)	N2—C6—H6A	109.8
O2—S1—O3	112.97 (8)	C1—C6—H6A	109.8
O1—S1—O3	110.02 (7)	N2—C6—H6B	109.8
O2—S1—C8	107.25 (8)	C1—C6—H6B	109.8
O1—S1—C8	105.88 (7)	H6A—C6—H6B	108.3
O3—S1—C8	106.40 (7)	N2—C7—C8	111.68 (12)
S1—O3—Ni1	129.73 (6)	N2—C7—H7A	109.3
C5—N1—C1	118.73 (14)	C8—C7—H7A	109.3
C5—N1—Ni1	127.92 (11)	N2—C7—H7B	109.3
C1—N1—Ni1	113.01 (10)	C8—C7—H7B	109.3
C6—N2—C7	109.81 (12)	H7A—C7—H7B	107.9
C6—N2—Ni1	105.53 (9)	C7—C8—S1	112.62 (10)
C7—N2—Ni1	116.81 (9)	C7—C8—H8A	109.1
C6—N2—H1N	105.4 (12)	S1—C8—H8A	109.1
C7—N2—H1N	106.7 (12)	C7—C8—H8B	109.1
Ni1—N2—H1N	112.0 (12)	S1—C8—H8B	109.1
N1—C1—C2	121.91 (17)	H8A—C8—H8B	107.8
O2—S1—O3—Ni1	101.05 (11)	N2^i—Ni1—N2—C7	160 (17)
O1—S1—O3—Ni1	−130.63 (9)	N1^i—Ni1—N2—C7	90.36 (11)
C8—S1—O3—Ni1	−16.37 (11)	N1—Ni1—N2—C7	−89.64 (11)
O3^i—Ni1—O3—S1	−153 (8)	C5—N1—C1—C2	−1.3 (3)
N2—Ni1—O3—S1	36.51 (10)	Ni1—N1—C1—C2	172.59 (15)
N2^i—Ni1—O3—S1	−143.49 (10)	C5—N1—C1—C6	179.00 (14)
N1^i—Ni1—O3—S1	−64.52 (10)	Ni1—N1—C1—C6	−7.13 (17)
N1—Ni1—O3—S1	115.48 (10)	N1—C1—C2—C3	0.7 (3)
O3—Ni1—N1—C5	65.02 (14)	C6—C1—C2—C3	−179.6 (2)
O3^i—Ni1—N1—C5	−114.98 (14)	C1—C2—C3—C4	0.2 (4)
N2—Ni1—N1—C5	158.22 (14)	C2—C3—C4—C5	−0.6 (4)
N2^i—Ni1—N1—C5	−21.78 (14)	C1—N1—C5—C4	0.9 (3)
N1^i—Ni1—N1—C5	76 (30)	Ni1—N1—C5—C4	−171.96 (16)
O3—Ni1—N1—C1	−108.16 (11)	C3—C4—C5—N1	0.0 (4)
O3^i—Ni1—N1—C1	71.84 (11)	C7—N2—C6—C1	81.22 (15)
N2—Ni1—N1—C1	−14.97 (11)	Ni1—N2—C6—C1	−45.48 (14)
N2^i—Ni1—N1—C1	165.03 (11)	N1—C1—C6—N2	36.05 (19)
N1^i—Ni1—N1—C1	−97 (30)	C2—C1—C6—N2	−143.67 (17)
O3—Ni1—N2—C6	121.09 (10)	C6—N2—C7—C8	−171.05 (12)
O3^i—Ni1—N2—C6	−58.91 (10)	Ni1—N2—C7—C8	−50.99 (15)
N2^i—Ni1—N2—C6	−78 (17)	N2—C7—C8—S1	83.95 (13)
N1^i—Ni1—N2—C6	−147.33 (9)	O2—S1—C8—C7	−166.32 (11)
N1—Ni1—N2—C6	32.67 (9)	O1—S1—C8—C7	71.88 (12)
O3—Ni1—N2—C7	−1.22 (10)	O3—S1—C8—C7	−45.17 (12)
O3^i—Ni1—N2—C7	178.78 (10)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1^ii	0.847 (18)	2.100 (19)	2.9394 (17)	170.6 (16)

Symmetry code: (ii) x, −y+1/2, z−1/2.