Diaqua­bis[2-(benzyl­oxy)acetato]cobalt(II)

Chen, C.-L.; Sun, S.-L.; Gu, C.-S.; Song, W.-D.; Hao, X.-M.

doi:10.1107/S1600536808016899

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m890

doi:10.1107/S1600536808016899

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Diaquabis[2-(benzyloxy)acetato]cobalt(II)

Chun-Liang Chen,^a Sheng-Li Sun,^a Chang-Sheng Gu,^b ^* Weng-Dong Song ^b and Xiao-Min Hao ^b

^aMonitoring Center of Marine Resources and the Environment, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China, and ^bDepartment of Applied Chemistry, Guangdong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: liujiwei0706@163.com

(Received 22 April 2008; accepted 3 June 2008; online 7 June 2008)

In the mononuclear title complex, [Co(C₉H₉O₃)₂(H₂O)₂], each Co^II atom is located on an inversion center and is hexacoordinated by four O atoms from two benzyloxyacetate ligands [Co—O bond lengths = 2.0487 (9) and 2.1090 (9) Å] and two water molecules [Co—O bond length = 2.0873 (9) Å] in a distorted octahedral geometry. In the crystal structure, intermolecular hydrogen bonds and π–π stacking interactions [centroid–centroid distance between phenyl rings = 3.692 (2) Å] link the molecules into a supramolecular structure.

Related literature

For the crystal structure of a similar Cu^II complex of benzyloxyacetate, see: Sun et al. (2008 ).

Experimental

Crystal data

[Co(C₉H₉O₃)₂(H₂O)₂]
M_r = 425.29
Monoclinic, P 2₁ /c
a = 11.4968 (1) Å
b = 7.1557 (1) Å
c = 12.0054 (1) Å
β = 109.708 (1)°
V = 929.80 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 296 (2) K
0.32 × 0.26 × 0.18 mm

Data collection

Bruker P4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.743, T_max = 0.835
7958 measured reflections
2126 independent reflections
1904 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.066
S = 1.07
2115 reflections
131 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2ⁱ	0.84 (2)	1.94 (1)	2.768 (2)	169 (2)
O1W—H1W2⋯O2ⁱⁱ	0.846 (9)	1.94 (1)	2.773 (1)	171 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016899/lx2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016899/lx2056Isup2.hkl

checkCIF report

Comment top

Recently, we have reported the crystal structure of the complex of benzyloxyacetate, [Cu(C₉H₉O₃)₂.2(H₂O)], (Sun et al., 2008). Here we report the crystal structure of the title mononuclear complex of benzyloxyacetate, [Co(C₉H₉O₃)₂.2(H₂O)], (Fig. 1).

The structure of the title compound is similar to that of the Cu(II) complex (Sun et al., 2008). The Co atom lies on an inversion center and displays an octahedral geometry defined by two carboxylate O atoms and two benzyloxy O atoms from two benzyloxyacetate ligands, and two water molecules, respectively. The Co—O and Co—Ow bond lengths are 2.0487 (9), 2.1090 (9) and 2.0873 (9) Å, respectively. The characteristic C—O(carboxylate) bond lengths suggest electron localization of the carboxylate groups of the anionic ligands. The molecular packing is stabilized by intermolecular O—H···O hydrogen bond interactions (Table 1). The crystal packing (Fig. 2) is further stabilized by aromatic π—π stacking interaction between the benzene ring from neighbouring molecules. The Cg···Cgⁱⁱ distance is 3.692 (2) Å (Cg is the centroids of the C4-C9 benzene ring, symmetry code as in Fig. 2).

Related literature top

For the crystal structure of similar CuII complex of benzyloxyacetate, see: Sun et al. (2008).

Experimental top

The ligand, benzyloxyacetic acid was commercially available and used without further purification. The title complex was prepared by the addition of Cobalt diacetate trihydrate (2.38 g, 10 mmol) to a hot aqueous solution of benzyloxyacetic acid (1.66 g, 10 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Pink prismatic crystals separated from the filtered solution after several days. C&H analysis. Calc. for C₁₈H₂₂CoO₈: C 50.83, H 5.21%. Found: C 50.81, H 5.22%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) with 30% probability ellipsoids. [Symmetry code: (i) -x, -y+1, -z+1.]
	Fig. 2. π—π interaction (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (ii) -x+1, -y+1, -z+1; (iii) x+1, y , z; (iv) -x+2, -y+1, -z+1; (v) x+2, y, z.]

Diaquabis[2-(benzyloxy)acetato]cobalt(II) top

Crystal data top

[Co(C₉H₉O₃)₂(H₂O)₂]	F(000) = 442
M_r = 425.29	D_x = 1.519 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7958 reflections
a = 11.4968 (1) Å	θ = 1.9–27.5°
b = 7.1557 (1) Å	µ = 0.97 mm⁻¹
c = 12.0054 (1) Å	T = 296 K
β = 109.708 (1)°	Prism, pink
V = 929.80 (2) Å³	0.32 × 0.26 × 0.18 mm
Z = 2

Data collection top

Bruker P4 diffractometer	2126 independent reflections
Radiation source: fine-focus sealed tube	1904 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −9→8
T_min = 0.743, T_max = 0.835	l = −15→15
7958 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0357P)² + 0.2056P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2115 reflections	Δρ_max = 0.27 e Å⁻³
131 parameters	Δρ_min = −0.23 e Å⁻³
3 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (3)

Crystal data top

[Co(C₉H₉O₃)₂(H₂O)₂]	V = 929.80 (2) Å³
M_r = 425.29	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4968 (1) Å	µ = 0.97 mm⁻¹
b = 7.1557 (1) Å	T = 296 K
c = 12.0054 (1) Å	0.32 × 0.26 × 0.18 mm
β = 109.708 (1)°

Data collection top

Bruker P4 diffractometer	2126 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1904 reflections with I > 2σ(I)
T_min = 0.743, T_max = 0.835	R_int = 0.020
7958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	3 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.27 e Å⁻³
2115 reflections	Δρ_min = −0.23 e Å⁻³
131 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.0000	0.5000	0.5000	0.02597 (10)
O1W	−0.07843 (9)	0.62124 (13)	0.33323 (8)	0.0367 (2)
O1	−0.04160 (8)	0.73017 (12)	0.58087 (8)	0.0344 (2)
O2	0.02557 (13)	1.00099 (11)	0.66922 (10)	0.0431 (3)
O3	0.15775 (8)	0.66897 (13)	0.52873 (8)	0.0349 (2)
C1	0.03731 (12)	0.85740 (17)	0.61469 (10)	0.0309 (3)
C2	0.15726 (12)	0.83967 (19)	0.58941 (12)	0.0363 (3)
C3	0.24243 (12)	0.6638 (2)	0.46413 (12)	0.0395 (3)
C4	0.37510 (12)	0.66780 (18)	0.54400 (12)	0.0339 (3)
C5	0.46331 (15)	0.7544 (2)	0.50689 (15)	0.0433 (3)
C6	0.58642 (15)	0.7538 (2)	0.57881 (19)	0.0553 (4)
C7	0.62120 (15)	0.6693 (2)	0.68845 (17)	0.0549 (4)
C8	0.53398 (15)	0.5825 (3)	0.72509 (15)	0.0523 (4)
C9	0.41170 (14)	0.5813 (2)	0.65364 (13)	0.0433 (3)
H2A	0.1659	0.9441	0.5413	0.044*
H2B	0.2264	0.8420	0.6631	0.044*
H3A	0.2269	0.7701	0.4110	0.047*
H3B	0.2279	0.5512	0.4165	0.047*
H5	0.4400	0.8132	0.4335	0.052*
H6	0.6456	0.8105	0.5531	0.066*
H7	0.7035	0.6711	0.7373	0.066*
H8	0.5575	0.5241	0.7986	0.063*
H9	0.3533	0.5219	0.6792	0.052*
H1W1	−0.0549 (19)	0.573 (2)	0.2805 (15)	0.065*
H1W2	−0.0696 (19)	0.7387 (13)	0.3341 (17)	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02885 (15)	0.01952 (14)	0.03148 (15)	−0.00140 (8)	0.01273 (10)	−0.00332 (8)
O1W	0.0462 (5)	0.0281 (5)	0.0367 (5)	0.0011 (4)	0.0153 (4)	0.0015 (4)
O1	0.0407 (5)	0.0245 (4)	0.0436 (5)	−0.0009 (4)	0.0216 (4)	−0.0046 (4)
O2	0.0696 (7)	0.0230 (5)	0.0448 (6)	−0.0019 (4)	0.0299 (5)	−0.0070 (4)
O3	0.0326 (4)	0.0299 (5)	0.0470 (5)	−0.0057 (4)	0.0197 (4)	−0.0106 (4)
C1	0.0446 (7)	0.0220 (6)	0.0275 (5)	0.0022 (5)	0.0139 (5)	0.0011 (5)
C2	0.0383 (7)	0.0265 (6)	0.0434 (7)	−0.0058 (5)	0.0126 (6)	−0.0080 (5)
C3	0.0362 (7)	0.0477 (8)	0.0386 (7)	−0.0027 (6)	0.0178 (5)	−0.0039 (6)
C4	0.0347 (6)	0.0295 (6)	0.0409 (7)	−0.0001 (5)	0.0170 (5)	−0.0025 (5)
C5	0.0432 (7)	0.0376 (8)	0.0559 (9)	−0.0003 (6)	0.0258 (7)	0.0035 (6)
C6	0.0400 (8)	0.0425 (9)	0.0919 (13)	−0.0059 (7)	0.0333 (8)	−0.0052 (9)
C7	0.0360 (7)	0.0473 (9)	0.0726 (11)	0.0065 (7)	0.0068 (7)	−0.0131 (8)
C8	0.0505 (9)	0.0526 (10)	0.0488 (8)	0.0164 (8)	0.0101 (7)	0.0011 (7)
C9	0.0440 (8)	0.0403 (8)	0.0491 (8)	0.0040 (6)	0.0202 (6)	0.0056 (7)

Geometric parameters (Å, º) top

Co1—O1	2.0487 (9)	C3—C4	1.503 (2)
Co1—O3	2.1090 (9)	C3—H3A	0.9700
Co1—O1W	2.0873 (9)	C3—H3B	0.9700
O1—C1	1.252 (2)	C4—C5	1.384 (2)
O2—C1	1.250 (2)	C4—C9	1.385 (2)
Co1—O1ⁱ	2.0487 (9)	C5—C6	1.387 (2)
Co1—O3ⁱ	2.1090 (9)	C5—H5	0.9300
Co1—O1Wⁱ	2.0873 (9)	C6—C7	1.380 (3)
O3—C2	1.423 (2)	C6—H6	0.9300
O3—C3	1.435 (2)	C7—C8	1.372 (3)
O1W—H1W1	0.84 (2)	C7—H7	0.9300
O1W—H1W2	0.846 (9)	C8—C9	1.378 (2)
C1—C2	1.514 (2)	C8—H8	0.9300
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700

O1—Co1—O1ⁱ	180.0	C1—C2—H2B	109.7
O1—Co1—O3	77.70 (3)	C2—O3—C3	114.77 (10)
O1—Co1—O3ⁱ	102.30 (3)	C2—O3—Co1	115.10 (7)
O1—Co1—O1W	91.49 (4)	C3—O3—Co1	126.84 (8)
O1—Co1—O1Wⁱ	88.51 (4)	C4—C3—H3A	109.1
O3ⁱ—Co1—O3	180.00 (7)	C4—C3—H3B	109.1
O1W—Co1—O3ⁱ	90.68 (4)	C4—C5—C6	120.18 (15)
O1W—Co1—O3	89.32 (4)	C4—C5—H5	119.9
O1Wⁱ—Co1—O1W	180.0	C4—C9—H9	119.7
Co1—O1W—H1W1	114.1 (14)	C5—C4—C9	119.03 (13)
Co1—O1W—H1W2	112.9 (13)	C5—C4—C3	119.94 (13)
O1ⁱ—Co1—O3	102.30 (3)	C5—C6—H6	119.9
O1ⁱ—Co1—O3ⁱ	77.70 (3)	C6—C5—H5	119.9
O1ⁱ—Co1—O1Wⁱ	91.49 (4)	C6—C7—H7	120.1
O1ⁱ—Co1—O1W	88.51 (4)	C7—C8—C9	120.38 (16)
O1Wⁱ—Co1—O3ⁱ	89.32 (4)	C7—C8—H8	119.8
O1Wⁱ—Co1—O3	90.68 (4)	C7—C6—C5	120.12 (15)
O1—C1—C2	118.90 (11)	C7—C6—H6	119.9
O2—C1—O1	124.96 (13)	C8—C7—C6	119.76 (15)
O2—C1—C2	116.14 (12)	C8—C7—H7	120.1
O3—C2—C1	109.61 (10)	C8—C9—C4	120.52 (15)
O3—C2—H2A	109.7	C8—C9—H9	119.7
O3—C2—H2B	109.7	C9—C4—C3	121.01 (12)
O3—C3—C4	112.47 (11)	C9—C8—H8	119.8
O3—C3—H3A	109.1	H1W1—O1W—H1W2	110.4 (14)
O3—C3—H3B	109.1	H2A—C2—H2B	108.2
C1—O1—Co1	118.60 (8)	H3A—C3—H3B	107.8
C1—C2—H2A	109.7

O1Wⁱ—Co1—O1—C1	88.19 (9)	Co1—O3—C2—C1	−1.77 (13)
O1W—Co1—O1—C1	−91.81 (9)	O2—C1—C2—O3	179.19 (11)
O3ⁱ—Co1—O1—C1	177.16 (9)	O1—C1—C2—O3	−0.56 (17)
O3—Co1—O1—C1	−2.84 (9)	C2—O3—C3—C4	67.25 (15)
O1—Co1—O3—C2	2.39 (9)	C1—O3—C3—C4	90.21 (17)
O1ⁱ—C1—O3—C2	−177.45 (11)	O3—C3—C4—C5	−147.57 (13)
O1Wⁱ—Co1—O3—C2	−85.93 (9)	O3—C3—C4—C9	34.23 (19)
O1W—Co1—O3—C2	94.07 (9)	C9—C4—C5—C6	0.1 (2)
O1—Co1—O3—C3	−155.88 (11)	C3—C4—C5—C6	−178.14 (14)
O1ⁱ—Co1—O3—C3	24.12 (11)	C4—C5—C6—C7	−1.0 (2)
O1Wⁱ—Co1—O3—C3	115.79 (11)	C5—C6—C7—C8	1.3 (3)
O1W—Co1—O3—C3	−64.21 (11)	C6—C7—C8—C9	−0.8 (3)
Co1—O1—C1—O2	−176.97 (10)	C7—C8—C9—C4	−0.1 (3)
Co1—O1—C1—C2	2.76 (15)	C5—C4—C9—C8	0.4 (2)
C3—O3—C2—C1	159.19 (11)	C3—C4—C9—C8	178.66 (14)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2ⁱⁱ	0.84 (2)	1.94 (1)	2.768 (2)	169 (2)
O1W—H1W2···O2ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.773 (1)	171 (2)

Symmetry codes: (ii) x, −y+3/2, z−1/2; (iii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₉H₉O₃)₂(H₂O)₂]
M_r	425.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4968 (1), 7.1557 (1), 12.0054 (1)
β (°)	109.708 (1)
V (Å³)	929.80 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.32 × 0.26 × 0.18

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.743, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	7958, 2126, 1904
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.066, 1.07
No. of reflections	2115
No. of parameters	131
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2ⁱ	0.84 (2)	1.94 (1)	2.768 (2)	169 (2)
O1W—H1W2···O2ⁱⁱ	0.846 (9)	1.94 (1)	2.773 (1)	171 (2)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, −y+2, −z+1.

Acknowledgements

The authors thank the Guangdong Ocean University Project (No. 0612178 and No. 0612179) and Zhanjiang City Technology Tender Project (No. 0810014) for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, S.-L., Chen, C.-L., Gu, C.-S., Song, W.-D. & Hao, X.-M. (2008). Acta Cryst. E64, m691. Web of Science CSD CrossRef IUCr Journals Google Scholar