Hexaaqua-cobalt(II) 2,2'-[naphthalene-1,8-diylbis(-oxy)]diacetate dihydrate.

In the title compound, [Co(H(2)O)(6)](C(14)H(10)O(6))·2H(2)O, the 2,2'-[naphthalene-1,8-diylbis(-oxy)]diacetate dianion L is not coordinated to the Co(II) ion. The asymmetric unit contains half of the L dianion, half of a [Co(H(2)O)(6)](2+) cation (both molecules being completed by inversion symmetry), and one water mol-ecule. The crystal packing features O-H⋯O hydrogen bonding between the carboxyl-ate groups, the aqua ligands and the hydrate water mol-ecules.

Related literature

In recent years, metal complexes have been synthezised with potential applications in mol­ecular sorption, electrical conductivity, catalysis, magnetism, non-linear optics and mol­ecular sensing, see: James (2003 ▶); Murray et al. (2009 ▶); Karmakar et al. (2009 ▶); Kurmoo (2009 ▶); Bradshaw et al. (2005 ▶). The 5-carboxymethoxy-naphtalene1-yl(oxy)-acetate ligand can provide a dominant packing feature and it often controls the supra­molecular assembly, see: Desiraju (2007 ▶). For Cd complexes with different co-ligands, see: Deka et al. (2011 ▶); Li et al. (2012 ▶) and for Zn complexes, see: Mondal et al. (2008 ▶).

Experimental

Crystal data

[Co(H2O)6](C14H10O6)·2H2O

M = 477.28

Triclinic,

a = 6.377 (2) Å

b = 6.642 (2) Å

c = 12.979 (5) Å

α = 79.669 (10)°

β = 79.963 (11)°

γ = 64.911 (8)°

V = 486.8 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.95 mm−1

T = 293 K

0.30 × 0.28 × 0.25 mm

Data collection

Siemens CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.731, T max = 1.000

3126 measured reflections

1678 independent reflections

1605 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.09

1678 reflections

161 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000512/vm2185sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000512/vm2185Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(H2O)6](C14H10O6)·2H2O	Z = 1
Mr = 477.28	F(000) = 249
Triclinic, P1	Dx = 1.628 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.377 (2) Å	Cell parameters from 1414 reflections
b = 6.642 (2) Å	θ = 3.2–27.5°
c = 12.979 (5) Å	µ = 0.95 mm−1
α = 79.669 (10)°	T = 293 K
β = 79.963 (11)°	Block, pink
γ = 64.911 (8)°	0.30 × 0.28 × 0.25 mm
V = 486.8 (3) Å3

Siemens CCD area-detector diffractometer	1678 independent reflections
Radiation source: fine-focus sealed tube	1605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −7→7
Tmin = 0.731, Tmax = 1.000	k = −7→7
3126 measured reflections	l = −15→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0408P)2 + 0.1833P] where P = (Fo2 + 2Fc2)/3
1678 reflections	(Δ/σ)max < 0.001
161 parameters	Δρmax = 0.37 e Å−3
12 restraints	Δρmin = −0.48 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.7658 (2)	0.7636 (3)	0.38143 (11)	0.0299 (3)
O2	0.9252 (3)	0.9376 (3)	0.20485 (12)	0.0374 (4)
O3	1.0787 (3)	1.1022 (3)	0.28675 (12)	0.0331 (4)
C5	0.5504 (3)	0.5494 (3)	0.45495 (15)	0.0222 (4)
C4	0.6759 (3)	0.6729 (3)	0.47211 (15)	0.0239 (4)
C3	0.6996 (3)	0.6953 (3)	0.57172 (16)	0.0275 (4)
H3	0.7826	0.7752	0.5816	0.033*
C2	0.5966 (3)	0.5961 (4)	0.65934 (16)	0.0282 (4)
H2	0.6115	0.6131	0.7269	0.034*
C1	0.4761 (3)	0.4762 (3)	0.64724 (15)	0.0257 (4)
H1	0.4113	0.4111	0.7062	0.031*
C6	0.8919 (3)	0.8899 (3)	0.39326 (15)	0.0254 (4)
H6A	1.0262	0.7948	0.4304	0.031*
H6B	0.7933	1.0118	0.4343	0.031*
C7	0.9709 (3)	0.9827 (3)	0.28607 (16)	0.0255 (4)
Co1	0.0000	0.5000	0.0000	0.03054 (16)
O7	0.5069 (3)	1.0109 (3)	0.83972 (12)	0.0387 (4)
O5	0.0045 (3)	0.5054 (3)	0.15926 (12)	0.0407 (4)
O6	0.3582 (3)	0.3007 (3)	−0.00989 (14)	0.0504 (5)
H6C	0.403 (6)	0.199 (5)	0.0532 (16)	0.075 (10)*
H6D	0.411 (6)	0.214 (5)	−0.0654 (18)	0.087 (12)*
H5A	−0.021 (6)	0.630 (4)	0.191 (2)	0.076 (10)*
H5B	0.013 (5)	0.385 (4)	0.211 (2)	0.067 (9)*
H7A	0.638 (3)	0.982 (5)	0.7915 (19)	0.062 (9)*
H7B	0.380 (4)	1.029 (6)	0.807 (2)	0.085 (11)*
O4	0.0880 (5)	0.7707 (3)	−0.03180 (15)	0.0629 (6)
H4A	0.2060	0.7419	−0.0738	0.094*
H4B	−0.043 (5)	0.897 (9)	−0.061 (4)	0.27 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0387 (8)	0.0372 (9)	0.0246 (7)	−0.0275 (7)	−0.0017 (6)	−0.0010 (6)
O2	0.0532 (9)	0.0444 (10)	0.0277 (8)	−0.0338 (8)	−0.0041 (7)	−0.0010 (7)
O3	0.0386 (8)	0.0346 (9)	0.0351 (8)	−0.0253 (7)	−0.0006 (6)	−0.0033 (6)
C5	0.0206 (8)	0.0211 (10)	0.0238 (9)	−0.0079 (7)	−0.0025 (7)	−0.0012 (7)
C4	0.0240 (9)	0.0241 (10)	0.0250 (10)	−0.0128 (8)	−0.0005 (7)	−0.0005 (8)
C3	0.0293 (10)	0.0295 (11)	0.0299 (11)	−0.0170 (8)	−0.0041 (8)	−0.0044 (8)
C2	0.0337 (10)	0.0323 (11)	0.0223 (10)	−0.0157 (9)	−0.0039 (8)	−0.0049 (8)
C1	0.0270 (9)	0.0288 (11)	0.0229 (10)	−0.0143 (8)	−0.0006 (7)	−0.0014 (8)
C6	0.0285 (9)	0.0254 (10)	0.0274 (10)	−0.0160 (8)	−0.0027 (8)	−0.0027 (8)
C7	0.0260 (9)	0.0231 (10)	0.0284 (11)	−0.0117 (8)	−0.0013 (8)	−0.0023 (8)
Co1	0.0457 (3)	0.0224 (2)	0.0229 (2)	−0.01429 (18)	−0.00138 (17)	−0.00230 (16)
O7	0.0332 (8)	0.0466 (10)	0.0329 (9)	−0.0127 (7)	−0.0026 (7)	−0.0068 (7)
O5	0.0655 (11)	0.0304 (9)	0.0257 (8)	−0.0194 (8)	−0.0046 (7)	−0.0026 (7)
O6	0.0605 (11)	0.0451 (11)	0.0359 (10)	−0.0118 (9)	−0.0026 (8)	−0.0085 (8)
O4	0.1209 (18)	0.0469 (12)	0.0407 (10)	−0.0550 (13)	−0.0101 (11)	0.0015 (9)

O1—C4	1.371 (2)	C6—H6B	0.9700
O1—C6	1.427 (2)	Co1—O4	2.056 (2)
O2—C7	1.257 (3)	Co1—O4ii	2.056 (2)
O3—C7	1.253 (3)	Co1—O5ii	2.0792 (17)
C5—C1i	1.414 (3)	Co1—O5	2.0792 (17)
C5—C5i	1.425 (4)	Co1—O6	2.093 (2)
C5—C4	1.431 (3)	Co1—O6ii	2.093 (2)
C4—C3	1.368 (3)	O7—H7A	0.921 (17)
C3—C2	1.413 (3)	O7—H7B	0.932 (17)
C3—H3	0.9300	O5—H5A	0.931 (17)
C2—C1	1.362 (3)	O5—H5B	0.933 (17)
C2—H2	0.9300	O6—H6C	0.962 (17)
C1—C5i	1.414 (3)	O6—H6D	0.929 (18)
C1—H1	0.9300	O4—H4A	0.8200
C6—C7	1.510 (3)	O4—H4B	0.97 (2)
C6—H6A	0.9700
C4—O1—C6	116.91 (15)	O4—Co1—O4ii	180.0
C1i—C5—C5i	119.8 (2)	O4—Co1—O5ii	91.63 (7)
C1i—C5—C4	122.26 (18)	O4ii—Co1—O5ii	88.37 (7)
C5i—C5—C4	117.9 (2)	O4—Co1—O5	88.37 (7)
C3—C4—O1	124.53 (18)	O4ii—Co1—O5	91.63 (7)
C3—C4—C5	121.27 (18)	O5ii—Co1—O5	180.00 (11)
O1—C4—C5	114.19 (17)	O4—Co1—O6	86.53 (10)
C4—C3—C2	119.38 (19)	O4ii—Co1—O6	93.47 (10)
C4—C3—H3	120.3	O5ii—Co1—O6	91.34 (7)
C2—C3—H3	120.3	O5—Co1—O6	88.66 (7)
C1—C2—C3	121.62 (18)	O4—Co1—O6ii	93.47 (10)
C1—C2—H2	119.2	O4ii—Co1—O6ii	86.53 (10)
C3—C2—H2	119.2	O5ii—Co1—O6ii	88.66 (7)
C2—C1—C5i	119.98 (18)	O5—Co1—O6ii	91.34 (7)
C2—C1—H1	120.0	O6—Co1—O6ii	180.00 (7)
C5i—C1—H1	120.0	H7A—O7—H7B	110 (2)
O1—C6—C7	109.63 (16)	Co1—O5—H5A	126.3 (19)
O1—C6—H6A	109.7	Co1—O5—H5B	123.8 (18)
C7—C6—H6A	109.7	H5A—O5—H5B	109 (2)
O1—C6—H6B	109.7	Co1—O6—H6C	112.4 (19)
C7—C6—H6B	109.7	Co1—O6—H6D	113 (2)
H6A—C6—H6B	108.2	H6C—O6—H6D	107 (2)
O3—C7—O2	125.29 (19)	Co1—O4—H4A	109.5
O3—C7—C6	115.32 (17)	Co1—O4—H4B	107 (4)
O2—C7—C6	119.39 (18)	H4A—O4—H4B	111.3

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6C···O7i	0.96 (2)	1.76 (3)	2.723 (3)	174 (3)
O6—H6D···O7iii	0.93 (2)	1.83 (3)	2.751 (3)	171 (3)
O5—H5A···O2iv	0.93 (3)	1.96 (3)	2.850 (3)	159 (2)
O5—H5B···O3v	0.94 (3)	1.87 (2)	2.783 (3)	165 (2)
O7—H7A···O3vi	0.92 (2)	1.82 (3)	2.736 (3)	171 (3)
O7—H7B···O2vii	0.93 (3)	1.89 (3)	2.780 (3)	158 (2)

Table 1

Selected bond lengths (Å)

Co1—O4	2.056 (2)
Co1—O5	2.0792 (17)
Co1—O6	2.093 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6C⋯O7i	0.96 (2)	1.76 (3)	2.723 (3)	174 (3)
O6—H6D⋯O7ii	0.93 (2)	1.83 (3)	2.751 (3)	171 (3)
O5—H5A⋯O2iii	0.93 (3)	1.96 (3)	2.850 (3)	159 (2)
O5—H5B⋯O3iv	0.94 (3)	1.87 (2)	2.783 (3)	165 (2)
O7—H7A⋯O3v	0.92 (2)	1.82 (3)	2.736 (3)	171 (3)
O7—H7B⋯O2vi	0.93 (3)	1.89 (3)	2.780 (3)	158 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .