Hexaaqua­cobalt(II) 2,2′-[naphthalene-1,8-diylbis(­oxy)]diacetate dihydrate

Shi, H.F.; Wu, T.; Jiang, P.G.; Hao, Z.; Zhang, M.M.

doi:10.1107/S1600536813000512

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages m103-m104

doi:10.1107/S1600536813000512

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Hexaaquacobalt(II) 2,2′-[naphthalene-1,8-diylbis(oxy)]diacetate dihydrate

Hui Fang Shi,^a ^* Tao Wu,^a Peng Gang Jiang,^a Zhi Hao ^a and Miao Miao Zhang ^a

^aDepartment of Chemistry, College of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, People's Republic of China
^*Correspondence e-mail: shishipiaoliang@126.com

(Received 19 December 2012; accepted 7 January 2013; online 12 January 2013)

In the title compound, [Co(H₂O)₆](C₁₄H₁₀O₆)·2H₂O, 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(H₂O)₆]²⁺ cation (both molecules being completed by inversion symmetry), and one water molecule. The crystal packing features O—H⋯O hydrogen bonding between the carboxylate groups, the aqua ligands and the hydrate water molecules.

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_r = 477.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.09
1678 reflections
161 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.48 e Å⁻³

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⋯O3^iv	0.94 (3)	1.87 (2)	2.783 (3)	165 (2)
O7—H7A⋯O3^v	0.92 (2)	1.82 (3)	2.736 (3)	171 (3)
O7—H7B⋯O2^vi	0.93 (3)	1.89 (3)	2.780 (3)	158 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z-1; (iii) x-1, y, z; (iv) x-1, y-1, z; (v) -x+2, -y+2, -z+1; (vi) -x+1, -y+2, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813000512/vm2185sup1.cif

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

checkCIF report

Comment top

In recent years, metal complexes have been synthezised with potential applications in molecular sorption, electrical conductivity, catalysis, magnetism, nonlinear optics, and molecular sensing (James, 2003; Murray et al., 2009; Kurmoo, 2009; Karmakar et al., 2009; Bradshaw et al., 2005). The LH2 ligand (5-carboxymethoxy-naphtalen-1-yloxy)-acetic acid) has received our attention because it can provide a dominant packing feature and it often controls the supramolecular assembly (Desiraju et al., 2007). At present, many of its metal complexes have already been reported, but most are focused on Cd complexes (Deka et al., 2011; Li et al., 2012) and Zn complexes (Li et al., 2012) with different co-ligands such as 2,2-bipyridine or 1,10-phenanthroline (phen). In the present paper, we hydrothermally synthesized a novel coordination complex constructed by Co^II, L and water molecules and determined its crystal structure (Fig. 1).

The asymmetric unit of the complex consists of a half ligand L, a half Co^II ion complexed with three water molecules and one additional water molecule. The Co^II center is octahedrally coordinated by six water molecules. The two carboxylate arms of the LH2 ligand lie in the same plane as the naphthalene ring. The hydrogen atoms of the water molecular and the oxygen atoms which are coordinated by Co^II are involved in hydrogen bonding with the oxygen atoms of the carboxylate group (Table 2, Fig. 2). In this case a sheet-like structure is formed.

Related literature top

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-naphtalen-1-yloxy)-acetic acid 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 top

The ligand LH2 was synthesized according to the procedure published by Mondal et al. (2008).

A mixture of Co(NO₃)₂.6H₂O (0.05 mmol, 0.015 g), L (0.05 mmol, 0.013 g), water (1 ml) and DMF (1 ml) was heated at 393 K in a Teflon-lined autoclave for three days, followed by slow cooling to room temperature. The resulting pink block crystals were filtered off and washed with distilled water.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular structure of (I), with the atomic numbering scheme and displacement ellipsoids at the 50% probability level (H atoms omitted for clarity) [symmetry codes: (A) -x + 1, -y + 1, -z + 1, (B) -x, -y + 1, -z.].
	Fig. 2. Three dimensional supramolecular architecture constructed by intermolecular hydrogen bonds. The dotted lines indicate the hydrogen bonds.

Hexaaquacobalt(II) 2,2'-[naphthalene-1,8-diylbis(oxy)]diacetate dihydrate top

Crystal data top

[Co(H₂O)₆](C₁₄H₁₀O₆)·2H₂O	Z = 1
M_r = 477.28	F(000) = 249
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.031	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(F_o²) + (0.0408P)² + 0.1833P] where P = (F_o² + 2F_c²)/3
1678 reflections	(Δ/σ)_max < 0.001
161 parameters	Δρ_max = 0.37 e Å⁻³
12 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Co(H₂O)₆](C₁₄H₁₀O₆)·2H₂O	γ = 64.911 (8)°
M_r = 477.28	V = 486.8 (3) Å³
Triclinic, P1	Z = 1
a = 6.377 (2) Å	Mo Kα radiation
b = 6.642 (2) Å	µ = 0.95 mm⁻¹
c = 12.979 (5) Å	T = 293 K
α = 79.669 (10)°	0.30 × 0.28 × 0.25 mm
β = 79.963 (11)°

Data collection top

Siemens CCD area-detector diffractometer	1678 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1605 reflections with I > 2σ(I)
T_min = 0.731, T_max = 1.000	R_int = 0.018
3126 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	12 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.37 e Å⁻³
1678 reflections	Δρ_min = −0.48 e Å⁻³
161 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.93 (3)	1.96 (3)	2.850 (3)	159 (2)
O5—H5B···O3^v	0.94 (3)	1.87 (2)	2.783 (3)	165 (2)
O7—H7A···O3^vi	0.92 (2)	1.82 (3)	2.736 (3)	171 (3)
O7—H7B···O2^vii	0.93 (3)	1.89 (3)	2.780 (3)	158 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x, y−1, z−1; (iv) x−1, y, z; (v) x−1, y−1, z; (vi) −x+2, −y+2, −z+1; (vii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(H₂O)₆](C₁₄H₁₀O₆)·2H₂O
M_r	477.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.377 (2), 6.642 (2), 12.979 (5)
α, β, γ (°)	79.669 (10), 79.963 (11), 64.911 (8)
V (Å³)	486.8 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.30 × 0.28 × 0.25

Data collection
Diffractometer	Siemens CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.731, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3126, 1678, 1605
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.09
No. of reflections	1678
No. of parameters	161
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.48

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.94 (3)	1.87 (2)	2.783 (3)	165 (2)
O7—H7A···O3^v	0.92 (2)	1.82 (3)	2.736 (3)	171 (3)
O7—H7B···O2^vi	0.93 (3)	1.89 (3)	2.780 (3)	158 (2)

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

Acknowledgements

This work was supported by the Fundamental Research Funds for the Central Universities (No. CQDXWL-2012–024).

References

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