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Acta Cryst. (2007). E63, m2353    [ doi:10.1107/S1600536807039633 ]

Tetraaquabis(1,3-di-4-pyridylpropane-[kappa]N)cobalt(II) bis(4-aminonaphthalene-1-sulfonate)

L.-W. Mi, M.-L. Han, W.-F. Xiao and S. W. Ng

Abstract top

The CoII atom in the crystal structure of the title compound, [Co(C13H14N2)2(H2O)4](C10H8NO3S)2, lies on a center of inversion in an N2O4 octahedron. The sulfonate anion interacts with the cation through hydrogen bonds, giving rise to a three-dimensional network.

Comment top

Among metal sulfonates, some have the sulfonate anion directly bonded to the metal center whereas other have the anion in an outer-sphere type of coordination, the anion interacting indirectly through hydrogen bonds (Cai, 2004). The few metal 4-amino-naphthalenesulfonates that have been identified by crystallography show this feature (Li et al., 2005; Li et al., 2006; Zhou et al., 2005). The cobalt(II) atom in the title compound lies on a center-of-inversion in an N2O4 octahedron (see Table 1). The sulfonate anion interacts with the cation through hydrogen bonds (see Table 2), these giving rise to a three-dimensional network,

Related literature top

For a crystallographic review of metal arenesulfonates, see Cai (2004). For examples of metal 4-amino-naphthalenesulfonates in which the anion is not directly bonded to the metal, see Li et al. (2006) and Zhou et al. (2005) for the cadmium salts, and Li et al. (2005) for the copper salt.

Experimental top

To cobalt(II) nitrate (1 mmol) dissolved in water was sodium 4-amino-naphthalene sulfonate (1 mmol) dissolved in methanol. 1,3-Bis(4-pyridyl)propane (1 mmol) dissolved in methanol was then added. Large red crystals separated from the solution after several days (in 80% yield).

Refinement top

The water and amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H = N–H = 0.85±0.01 Å; their displacement parameters were freely refined. The carbon-bound H-atoms were generated geometrically (C–H 0.93 to 0.97 Å); they were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot depicting the coordination geometry of cobalt; displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius·[Symmetry code (i): 1 – x, 1 – y, 1 − z.]
Tetraaquabis(1,3-di-4-pyridylpropane-κN)cobalt(II) bis(4-aminonaphthalene-1-sulfonate) top
Crystal data top
[Co(C13H14N2)2(H2O)4](C10H8NO3S)2F000 = 1018
Mr = 971.99Dx = 1.365 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 743 reflections
a = 9.7790 (6) Åθ = 2.5–28.2º
b = 16.261 (1) ŵ = 0.51 mm−1
c = 15.375 (1) ÅT = 295 (2) K
β = 104.625 (1)ºBlock, red
V = 2365.6 (3) Å30.42 × 0.31 × 0.26 mm
Z = 2
Data collection top
Bruker APEX II area-detector
diffractometer		5383 independent reflections
Radiation source: fine-focus sealed tube4524 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.017
T = 295(2) Kθmax = 27.5º
φ and ω scansθmin = 2.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→12
Tmin = 0.759, Tmax = 0.878k = −21→21
16557 measured reflectionsl = −18→19
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)] = 0.031H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.089  w = 1/[σ2(Fo2) + (0.0499P)2 + 0.4354P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5383 reflectionsΔρmax = 0.27 e Å−3
319 parametersΔρmin = −0.31 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Co(C13H14N2)2(H2O)4](C10H8NO3S)2V = 2365.6 (3) Å3
Mr = 971.99Z = 2
Monoclinic, P21/cMo Kα
a = 9.7790 (6) ŵ = 0.51 mm−1
b = 16.261 (1) ÅT = 295 (2) K
c = 15.375 (1) Å0.42 × 0.31 × 0.26 mm
β = 104.625 (1)º
Data collection top
Bruker APEX II area-detector
diffractometer		5383 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4524 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 0.878Rint = 0.017
16557 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0316 restraints
wR(F2) = 0.089H atoms treated by a mixture of
independent and constrained refinement
S = 1.03Δρmax = 0.27 e Å−3
5383 reflectionsΔρmin = −0.31 e Å−3
319 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.50000.50000.50000.03216 (9)
S10.04035 (4)0.59566 (2)0.64502 (2)0.04044 (11)
O10.17834 (13)0.56048 (8)0.64976 (8)0.0567 (3)
O2−0.02305 (14)0.63540 (8)0.55948 (8)0.0586 (3)
O3−0.05603 (13)0.53643 (8)0.66932 (8)0.0535 (3)
O1W0.35327 (13)0.58214 (8)0.53205 (8)0.0472 (3)
H110.2855 (17)0.5976 (12)0.4894 (11)0.067 (6)*
H120.315 (2)0.5725 (13)0.5741 (11)0.067 (6)*
O2W0.65302 (13)0.55626 (8)0.60223 (7)0.0481 (3)
H210.7406 (11)0.5579 (13)0.6092 (14)0.063 (6)*
H220.640 (2)0.5608 (14)0.6540 (8)0.077 (7)*
N10.53869 (13)0.58325 (8)0.39844 (8)0.0360 (3)
N20.62516 (18)0.57641 (11)−0.22209 (10)0.0620 (4)
N30.10056 (15)0.87085 (8)0.90985 (9)0.0418 (3)
H310.0643 (17)0.8627 (10)0.9540 (9)0.042 (5)*
H320.0650 (18)0.9146 (8)0.8821 (11)0.046 (5)*
C10.43213 (18)0.61539 (11)0.33443 (11)0.0466 (4)
H10.34000.60530.33790.056*
C20.45187 (19)0.66237 (11)0.26416 (11)0.0498 (4)
H20.37440.68380.22220.060*
C30.58785 (19)0.67768 (10)0.25596 (10)0.0440 (4)
C40.69713 (18)0.64612 (10)0.32255 (11)0.0473 (4)
H40.79010.65560.32070.057*
C50.66959 (17)0.60054 (10)0.39194 (10)0.0412 (3)
H50.74570.58090.43630.049*
C60.6135 (2)0.72465 (11)0.17690 (11)0.0547 (4)
H6A0.70180.75460.19590.066*
H6B0.53830.76450.15680.066*
C70.6199 (2)0.66793 (10)0.09830 (10)0.0502 (4)
H7A0.69770.62960.11740.060*
H7B0.53310.63640.08050.060*
C80.6399 (2)0.71753 (11)0.01797 (11)0.0559 (4)
H8A0.56610.75880.00260.067*
H8B0.72980.74600.03520.067*
C90.5088 (2)0.59422 (16)−0.19520 (14)0.0721 (6)
H90.42220.5763−0.23040.086*
C100.5104 (2)0.63766 (15)−0.11825 (13)0.0639 (5)
H100.42610.6482−0.10270.077*
C110.63622 (19)0.66574 (11)−0.06400 (10)0.0473 (4)
C120.75670 (19)0.64531 (13)−0.09045 (11)0.0563 (5)
H1210.84490.6610−0.05540.068*
C130.7465 (2)0.60173 (13)−0.16871 (13)0.0609 (5)
H130.82950.5894−0.18500.073*
C140.06477 (15)0.67457 (9)0.72696 (9)0.0347 (3)
C150.03967 (16)0.75405 (9)0.69763 (10)0.0402 (3)
H150.01360.76480.63620.048*
C160.05262 (17)0.81950 (9)0.75851 (10)0.0408 (3)
H160.03680.87300.73700.049*
C170.08839 (15)0.80554 (8)0.84941 (9)0.0342 (3)
C180.11955 (15)0.72344 (8)0.88304 (9)0.0338 (3)
C190.16225 (18)0.70681 (10)0.97662 (10)0.0454 (4)
H190.17180.75001.01740.054*
C200.1896 (2)0.62808 (11)1.00766 (12)0.0574 (5)
H200.21570.61801.06920.069*
C210.1782 (2)0.56277 (11)0.94689 (13)0.0579 (5)
H2110.19730.50950.96850.069*
C220.13945 (18)0.57630 (10)0.85632 (11)0.0465 (4)
H2210.13350.53220.81710.056*
C230.10801 (15)0.65683 (9)0.82121 (9)0.0343 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02968 (15)0.04245 (16)0.02514 (13)0.00390 (11)0.00836 (10)0.00034 (10)
S10.0375 (2)0.0465 (2)0.0397 (2)−0.00494 (16)0.01423 (16)−0.01240 (15)
O10.0469 (7)0.0694 (8)0.0596 (7)0.0074 (6)0.0247 (6)−0.0138 (6)
O20.0647 (8)0.0700 (8)0.0381 (6)−0.0011 (7)0.0075 (6)−0.0122 (5)
O30.0531 (7)0.0504 (7)0.0613 (7)−0.0169 (6)0.0224 (6)−0.0178 (6)
O1W0.0430 (7)0.0627 (7)0.0386 (6)0.0179 (5)0.0151 (5)0.0059 (5)
O2W0.0384 (7)0.0732 (8)0.0326 (6)−0.0061 (6)0.0085 (5)−0.0093 (5)
N10.0342 (6)0.0458 (7)0.0290 (6)0.0041 (5)0.0096 (5)0.0005 (5)
N20.0634 (10)0.0840 (11)0.0420 (8)−0.0129 (9)0.0198 (7)−0.0087 (7)
N30.0493 (8)0.0349 (7)0.0418 (7)−0.0032 (6)0.0127 (6)−0.0047 (5)
C10.0368 (8)0.0635 (10)0.0404 (8)0.0056 (7)0.0116 (7)0.0089 (7)
C20.0489 (10)0.0612 (10)0.0375 (8)0.0078 (8)0.0074 (7)0.0107 (7)
C30.0601 (10)0.0413 (8)0.0349 (7)−0.0015 (7)0.0199 (7)−0.0023 (6)
C40.0429 (9)0.0555 (9)0.0479 (9)−0.0028 (7)0.0198 (7)0.0008 (7)
C50.0358 (8)0.0499 (9)0.0382 (8)0.0022 (7)0.0098 (6)0.0014 (6)
C60.0803 (13)0.0478 (9)0.0426 (9)−0.0027 (9)0.0276 (9)0.0034 (7)
C70.0684 (12)0.0492 (9)0.0370 (8)−0.0014 (8)0.0209 (8)0.0042 (6)
C80.0754 (13)0.0560 (10)0.0405 (8)−0.0084 (9)0.0228 (8)0.0040 (7)
C90.0514 (12)0.1150 (18)0.0483 (11)−0.0213 (12)0.0099 (9)−0.0140 (11)
C100.0437 (10)0.1006 (16)0.0516 (10)−0.0075 (10)0.0195 (8)−0.0068 (10)
C110.0537 (10)0.0561 (9)0.0335 (7)−0.0064 (8)0.0137 (7)0.0089 (6)
C120.0427 (9)0.0831 (13)0.0414 (9)−0.0087 (9)0.0075 (7)0.0015 (8)
C130.0491 (11)0.0883 (14)0.0495 (10)−0.0010 (10)0.0206 (8)−0.0010 (9)
C140.0304 (7)0.0391 (7)0.0359 (7)−0.0036 (6)0.0106 (6)−0.0053 (5)
C150.0420 (8)0.0457 (8)0.0326 (7)−0.0018 (7)0.0086 (6)0.0006 (6)
C160.0460 (9)0.0348 (7)0.0410 (8)0.0015 (6)0.0099 (7)0.0035 (6)
C170.0297 (7)0.0347 (7)0.0386 (7)−0.0042 (5)0.0093 (6)−0.0039 (5)
C180.0292 (7)0.0371 (7)0.0348 (7)−0.0027 (6)0.0078 (6)−0.0006 (5)
C190.0495 (9)0.0483 (9)0.0367 (8)−0.0007 (7)0.0078 (7)−0.0017 (6)
C200.0719 (13)0.0576 (10)0.0395 (9)0.0064 (9)0.0083 (8)0.0104 (7)
C210.0728 (13)0.0425 (9)0.0567 (10)0.0083 (9)0.0134 (9)0.0134 (7)
C220.0519 (10)0.0356 (8)0.0518 (9)0.0014 (7)0.0129 (8)−0.0008 (6)
C230.0294 (7)0.0362 (7)0.0378 (7)−0.0021 (6)0.0095 (6)−0.0015 (5)
Geometric parameters (Å, °) top
Co1—O1w2.108 (1)C6—H6B0.9700
Co1—O2w2.088 (1)C7—C81.528 (2)
Co1—N12.171 (1)C7—H7A0.9700
Co1—O2wi2.088 (1)C7—H7B0.9700
Co1—O1wi2.108 (1)C8—C111.509 (2)
Co1—N1i2.171 (1)C8—H8A0.9700
S1—O11.4504 (12)C8—H8B0.9700
S1—O21.4560 (13)C9—C101.375 (3)
S1—O31.4606 (12)C9—H90.9300
S1—C141.7717 (14)C10—C111.378 (3)
O1W—H110.84 (1)C10—H100.9300
O1W—H120.84 (1)C11—C121.380 (2)
O2W—H210.84 (1)C12—C131.378 (3)
O2W—H220.84 (1)C12—H1210.9300
N1—C51.339 (2)C13—H130.9300
N1—C11.345 (2)C14—C151.370 (2)
N2—C131.326 (3)C14—C231.4327 (19)
N2—C91.337 (3)C15—C161.402 (2)
N3—C171.3962 (18)C15—H150.9300
N3—H310.85 (1)C16—C171.371 (2)
N3—H320.86 (1)C16—H160.9300
C1—C21.376 (2)C17—C181.4363 (19)
C1—H10.9300C18—C191.419 (2)
C2—C31.390 (2)C18—C231.4266 (19)
C2—H20.9300C19—C201.369 (2)
C3—C41.379 (2)C19—H190.9300
C3—C61.509 (2)C20—C211.400 (3)
C4—C51.380 (2)C20—H200.9300
C4—H40.9300C21—C221.365 (2)
C5—H50.9300C21—H2110.9300
C6—C71.534 (2)C22—C231.420 (2)
C6—H6A0.9700C22—H2210.9300
O2Wi—Co1—O2W180.0C8—C7—H7A109.4
O2Wi—Co1—O1W93.03 (5)C6—C7—H7A109.4
O2W—Co1—O1W86.97 (5)C8—C7—H7B109.4
O2Wi—Co1—O1Wi86.97 (5)C6—C7—H7B109.4
O2W—Co1—O1Wi93.03 (5)H7A—C7—H7B108.0
O1W—Co1—O1Wi180.0C11—C8—C7113.56 (14)
O2Wi—Co1—N187.34 (5)C11—C8—H8A108.9
O2W—Co1—N192.66 (5)C7—C8—H8A108.9
O1W—Co1—N191.47 (5)C11—C8—H8B108.9
O1Wi—Co1—N188.53 (5)C7—C8—H8B108.9
O2Wi—Co1—N1i92.66 (5)H8A—C8—H8B107.7
O2W—Co1—N1i87.34 (5)N2—C9—C10123.52 (19)
O1W—Co1—N1i88.53 (5)N2—C9—H9118.2
O1Wi—Co1—N1i91.47 (5)C10—C9—H9118.2
N1—Co1—N1i180.00 (5)C9—C10—C11120.34 (18)
O1—S1—O2113.51 (8)C9—C10—H10119.8
O1—S1—O3112.29 (8)C11—C10—H10119.8
O2—S1—O3111.63 (8)C10—C11—C12116.10 (16)
O1—S1—C14107.05 (7)C10—C11—C8121.30 (17)
O2—S1—C14105.73 (7)C12—C11—C8122.58 (16)
O3—S1—C14105.99 (7)C13—C12—C11120.13 (17)
Co1—O1W—H11117.0 (15)C13—C12—H121119.9
Co1—O1W—H12121.5 (15)C11—C12—H121119.9
H11—O1W—H12104 (2)N2—C13—C12123.77 (18)
Co1—O2W—H21128.8 (14)N2—C13—H13118.1
Co1—O2W—H22120.1 (16)C12—C13—H13118.1
H21—O2W—H22106 (2)C15—C14—C23120.35 (13)
C5—N1—C1116.26 (13)C15—C14—S1117.93 (11)
C5—N1—Co1121.89 (10)C23—C14—S1121.72 (11)
C1—N1—Co1121.67 (11)C14—C15—C16121.19 (13)
C13—N2—C9116.09 (17)C14—C15—H15119.4
C17—N3—H31115.5 (12)C16—C15—H15119.4
C17—N3—H32110.1 (12)C17—C16—C15120.77 (14)
H31—N3—H32109 (2)C17—C16—H16119.6
N1—C1—C2123.62 (16)C15—C16—H16119.6
N1—C1—H1118.2C16—C17—N3120.62 (13)
C2—C1—H1118.2C16—C17—C18119.81 (13)
C1—C2—C3119.86 (15)N3—C17—C18119.52 (13)
C1—C2—H2120.1C19—C18—C23118.97 (13)
C3—C2—H2120.1C19—C18—C17121.56 (13)
C4—C3—C2116.49 (14)C23—C18—C17119.47 (12)
C4—C3—C6122.09 (16)C20—C19—C18120.87 (15)
C2—C3—C6121.40 (16)C20—C19—H19119.6
C3—C4—C5120.52 (15)C18—C19—H19119.6
C3—C4—H4119.7C19—C20—C21120.07 (16)
C5—C4—H4119.7C19—C20—H20120.0
N1—C5—C4123.18 (14)C21—C20—H20120.0
N1—C5—H5118.4C22—C21—C20120.87 (16)
C4—C5—H5118.4C22—C21—H211119.6
C3—C6—C7112.23 (13)C20—C21—H211119.6
C3—C6—H6A109.2C21—C22—C23120.91 (15)
C7—C6—H6A109.2C21—C22—H221119.5
C3—C6—H6B109.2C23—C22—H221119.5
C7—C6—H6B109.2C22—C23—C18118.28 (13)
H6A—C6—H6B107.9C22—C23—C14123.39 (13)
C8—C7—C6110.99 (14)C18—C23—C14118.33 (12)
O2Wi—Co1—N1—C5−132.91 (12)C11—C12—C13—N2−0.6 (3)
O2W—Co1—N1—C547.09 (12)O1—S1—C14—C15113.60 (13)
O1W—Co1—N1—C5134.13 (12)O2—S1—C14—C15−7.73 (14)
O1Wi—Co1—N1—C5−45.87 (12)O3—S1—C14—C15−126.36 (13)
O2Wi—Co1—N1—C142.01 (12)O1—S1—C14—C23−67.00 (13)
O2W—Co1—N1—C1−137.99 (12)O2—S1—C14—C23171.67 (12)
O1W—Co1—N1—C1−50.96 (13)O3—S1—C14—C2353.04 (14)
O1Wi—Co1—N1—C1129.04 (13)C23—C14—C15—C16−1.3 (2)
C5—N1—C1—C21.2 (2)S1—C14—C15—C16178.07 (12)
Co1—N1—C1—C2−173.96 (13)C14—C15—C16—C17−1.2 (2)
N1—C1—C2—C31.0 (3)C15—C16—C17—N3−179.70 (14)
C1—C2—C3—C4−2.2 (2)C15—C16—C17—C183.0 (2)
C1—C2—C3—C6176.33 (16)C16—C17—C18—C19177.55 (15)
C2—C3—C4—C51.2 (2)N3—C17—C18—C190.2 (2)
C6—C3—C4—C5−177.29 (15)C16—C17—C18—C23−2.2 (2)
C1—N1—C5—C4−2.3 (2)N3—C17—C18—C23−179.58 (13)
Co1—N1—C5—C4172.91 (12)C23—C18—C19—C20−1.2 (2)
C3—C4—C5—N11.1 (2)C17—C18—C19—C20179.03 (16)
C4—C3—C6—C788.7 (2)C18—C19—C20—C211.2 (3)
C2—C3—C6—C7−89.8 (2)C19—C20—C21—C22−0.3 (3)
C3—C6—C7—C8177.69 (17)C20—C21—C22—C23−0.7 (3)
C6—C7—C8—C11−175.75 (17)C21—C22—C23—C180.7 (2)
C13—N2—C9—C101.4 (3)C21—C22—C23—C14−179.02 (16)
N2—C9—C10—C110.2 (4)C19—C18—C23—C220.2 (2)
C9—C10—C11—C12−1.9 (3)C17—C18—C23—C22180.00 (14)
C9—C10—C11—C8176.58 (19)C19—C18—C23—C14179.99 (14)
C7—C8—C11—C1077.4 (2)C17—C18—C23—C14−0.3 (2)
C7—C8—C11—C12−104.1 (2)C15—C14—C23—C22−178.26 (15)
C10—C11—C12—C132.1 (3)S1—C14—C23—C222.4 (2)
C8—C11—C12—C13−176.35 (17)C15—C14—C23—C182.0 (2)
C9—N2—C13—C12−1.2 (3)S1—C14—C23—C18−177.38 (10)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H12···O10.84 (1)1.99 (1)2.809 (1)164 (2)
O1W—H11···N3ii0.84 (1)1.98 (1)2.807 (2)167 (2)
O2W—H21···O3iii0.84 (1)2.00 (1)2.790 (2)157 (2)
O2W—H22···N2iv0.84 (1)1.96 (1)2.802 (2)175 (2)
N3—H31···O2v0.85 (1)2.01 (1)2.858 (2)170 (2)
N3—H32···O3vi0.86 (1)2.13 (1)2.942 (2)159 (2)
Symmetry codes: (ii) x, −y+3/2, z−1/2; (iii) x+1, y, z; (iv) x, y, z+1; (v) x, −y+3/2, z+1/2; (vi) −x, y+1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H12···O10.84 (1)1.99 (1)2.809 (1)164 (2)
O1W—H11···N3i0.84 (1)1.98 (1)2.807 (2)167 (2)
O2W—H21···O3ii0.84 (1)2.00 (1)2.790 (2)157 (2)
O2W—H22···N2iii0.84 (1)1.96 (1)2.802 (2)175 (2)
N3—H31···O2iv0.85 (1)2.01 (1)2.858 (2)170 (2)
N3—H32···O3v0.86 (1)2.13 (1)2.942 (2)159 (2)
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x, −y+3/2, z+1/2; (v) −x, y+1/2, −z+3/2.
Acknowledgements top

We thank the National Science Foundation of China (project No. 20574058) and the University of Malaya for supporting this study.

references
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