catena-Poly[[diaquacobalt(II)]-bis(μ-3-carboxy­adamantane-1-carboxyl­ato-κ2O1:O3)]

Tang, L.-M.; Xu, J.-H.; Han, X.-Y.; Xu, W.

doi:10.1107/S1600536809007387

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m375

doi:10.1107/S1600536809007387

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catena-Poly[[diaquacobalt(II)]-bis(μ-3-carboxyadamantane-1-carboxylato-κ²O¹:O³)]

Li-Ming Tang,^a Jia-Hui Xu,^a Xiao-Yan Han ^a and Wei Xu ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical Engineering, Institute of Solid Materials Chemistry, Ningbo University, Ningbo, Zhejiang, 315211, People's Republic of China
^*Correspondence e-mail: zhengyueqing@nbu.edu.cn

(Received 27 February 2009; accepted 28 February 2009; online 6 March 2009)

In the title compound, [Co(C₁₂H₁₅O₄)₂(H₂O)₂]_n, adjacent Co^II atoms ( $[\overline1]$ symmetry) are bridged by 3-carboxyadamantane-1-carboxylate anions, forming a chain running along [001]. Interchain O—H⋯O hydrogen bonds link the chains into layers parallel to (100); the layers are further connected via interlayer hydrogen bonds interactions, forming a three-dimensional framework.

Related literature

For related compounds, see: Nielsen et al. (2008 ); Zhao et al. (2007 ); Zheng et al. (2008 ).

Experimental

Crystal data

[Co(C₁₂H₁₅O₄)₂(H₂O)₂]
M_r = 541.44
Orthorhombic, P c c n
a = 10.718 (2) Å
b = 23.638 (5) Å
c = 9.0726 (18) Å
V = 2298.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.921, T_max = 0.925
20865 measured reflections
2622 independent reflections
2145 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.086
S = 1.06
2622 reflections
161 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Co—O1	2.0574 (12)
Co—O5	2.0956 (14)
Co—O4ⁱ	2.1061 (12)
Symmetry code: (i) x, y, z-1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O1ⁱⁱ	0.81	1.82	2.6058 (19)	166
O5—H2⋯O2	0.80	2.07	2.7762 (18)	147
O5—H3⋯O2ⁱⁱⁱ	0.81	2.02	2.8334 (18)	175
Symmetry codes: (ii) x, y, z+1; (iii) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 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.

Supporting information

Crystal structure: contains datablocks ptcLa, I. DOI: 10.1107/S1600536809007387/ng2552sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007387/ng2552Isup2.hkl

checkCIF report

Comment top

The cambridge Structural Database (Version 5.30, February 2009) lists few examples of metal (II) adamantane-1,3-dicarboxylates (Nielsen et al., 2008; Zhao et al., 2007). The dicarboxylate group is rigid, much more different from the aliphatic dicarboxylic acids (Zheng et al., 2008), effected severely by spacial steric hindrance. The asymmetric unit of the title compoud consists of one Co²⁺ cation, one aqua ligand and one Hadc^- anion (H₂adc = adamantane-1,3-dicarboxylic acid) (Fig.1). The Co atoms at the Wckoff 4a sites are crystallographically imposed by iversion center and are each located in an elongated octahedral coordination sphere defined by two aqua ligands and four carboxylate oxygen atoms from four 3-carboxyadamantane-1-carboxylate anions. The axial Co—O bond distances averaged at 2.106 (1) Å are slightly longer than the equatorial ones of 2.078 (1) Å. The trans- and cisoid O—Co—O angles fall in the regions 88.49 (5)–91.51 (5)° and 180°, respectively, exhibiting slight diviation from the corresponding values for a regular geometry (Table 1). Each carboxylate anion monodentately coordinates one Co²⁺ ion in syn fashion. Interestingly, one of the two carboxylate anions from each ligand is protonated and coordinates one Co²⁺ ion by carbonyl oxygen atom, which is rare in former reports. The Co²⁺ ions are bridged by 3-carboxyadamantane-1-carboxylate anions to form one-dimensional chains running along the [001] direction. On the basis of the interchain O—H···O hydrogen bonds (Table 2),these chains are assembled into layers parallel to (100) (Fig.2). The layers are further connected to form a three-dimensional framework via interlayer hydrogen bonds interaction.

Related literature top

For related compounds, see: Nielsen et al. (2008); Zhao et al. (2007); Zheng et al. (2008).

Experimental top

Adamantane-1,3-dicarboxylic acid (H₂adc) (0.0666 g, 0.3 mmol), 1 M NaOH (0.5 ml, 0.5 mmol) was consequently added to 15 mol aqueous solution, then the mixture was heated constantly at 90 °C and stirred for 30 min, yielding colorless solution, to which was added CoCl₂.6H₂O (0.2485 g, 1.0 mmol) and continually stirred for 30 min, then the purple solution (pH = 5.12) was cooled to room temperature and laid undisturbed, purple block-like crystals was afforded after two weeks.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 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. View of the molecular structure of the title compound, Displacement ellipsoids are drawn at the 45% probability level.[Symmetry codes: (i) x, y, z + 1; (ii) -x + 1, -y + 1, -z; (iii) x, y, z - 1; (iv) -x + 1, -y + 1, -z + 1.]
	Fig. 2. The two-dimensional layer structure constructed by one-dimensional chains through hydrogen bonds interaction (the hydrogen bonds are neglected)

catena-Poly[[diaquacobalt(II)]-bis(µ-3-carboxyadamantane-1-carboxylato- κ²O¹:O³)] top

Crystal data top

[Co(C₁₂H₁₅O₄)₂(H₂O)₂]	F(000) = 1140
M_r = 541.44	D_x = 1.565 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 20865 reflections
a = 10.718 (2) Å	θ = 3.1–27.5°
b = 23.638 (5) Å	µ = 0.81 mm⁻¹
c = 9.0726 (18) Å	T = 293 K
V = 2298.6 (8) Å³	Block, purple
Z = 4	0.10 × 0.10 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2622 independent reflections
Radiation source: fine-focus sealed tube	2145 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −30→30
T_min = 0.921, T_max = 0.925	l = −11→11
20865 measured reflections

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) = 0.086	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0444P)² + 0.9177P] where P = (F_o² + 2F_c²)/3
2622 reflections	(Δ/σ)_max = 0.001
161 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Co(C₁₂H₁₅O₄)₂(H₂O)₂]	V = 2298.6 (8) Å³
M_r = 541.44	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 10.718 (2) Å	µ = 0.81 mm⁻¹
b = 23.638 (5) Å	T = 293 K
c = 9.0726 (18) Å	0.10 × 0.10 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2622 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2145 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.925	R_int = 0.033
20865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
2622 reflections	Δρ_min = −0.30 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
Co	0.5000	0.5000	0.0000	0.02148 (11)
C1	0.50924 (15)	0.62852 (7)	0.64285 (18)	0.0239 (3)
C2	0.37038 (16)	0.64210 (7)	0.61757 (18)	0.0300 (4)
H2A	0.3213	0.6077	0.6246	0.036*
H2B	0.3413	0.6683	0.6924	0.036*
C3	0.35442 (17)	0.66835 (9)	0.46523 (19)	0.0343 (4)
H3A	0.2660	0.6770	0.4490	0.041*
C4	0.39899 (16)	0.62682 (8)	0.34654 (18)	0.0310 (4)
H4A	0.3497	0.5924	0.3511	0.037*
H4B	0.3878	0.6435	0.2498	0.037*
C5	0.53696 (15)	0.61264 (7)	0.37055 (16)	0.0212 (3)
C6	0.55413 (17)	0.58683 (7)	0.52439 (16)	0.0256 (3)
H6A	0.6415	0.5780	0.5403	0.031*
H6B	0.5069	0.5519	0.5315	0.031*
C7	0.4296 (2)	0.72253 (8)	0.4553 (2)	0.0394 (5)
H7A	0.4012	0.7490	0.5297	0.047*
H7B	0.4176	0.7398	0.3593	0.047*
C8	0.56719 (19)	0.70952 (7)	0.47855 (19)	0.0327 (4)
H8A	0.6155	0.7446	0.4718	0.039*
C9	0.58580 (17)	0.68311 (7)	0.63123 (18)	0.0295 (4)
H9A	0.5594	0.7096	0.7068	0.035*
H9B	0.6735	0.6748	0.6465	0.035*
C10	0.61268 (16)	0.66778 (7)	0.36080 (18)	0.0278 (4)
H10A	0.7005	0.6597	0.3758	0.033*
H10B	0.6028	0.6844	0.2637	0.033*
C11	0.58484 (15)	0.57136 (7)	0.25371 (16)	0.0247 (3)
O1	0.52461 (12)	0.56998 (5)	0.13165 (12)	0.0296 (3)
O2	0.67854 (12)	0.54217 (6)	0.27703 (13)	0.0378 (3)
C12	0.51789 (16)	0.60130 (7)	0.79318 (18)	0.0280 (4)
O3	0.51926 (19)	0.63717 (6)	0.90404 (15)	0.0615 (5)
H1	0.5154	0.6209	0.9823	0.074*
O4	0.51779 (12)	0.55044 (5)	0.80980 (13)	0.0312 (3)
O5	0.69310 (12)	0.48644 (6)	0.00823 (12)	0.0314 (3)
H2	0.7197	0.5019	0.0807	0.038*
H3	0.7333	0.5010	−0.0575	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.02775 (18)	0.02296 (17)	0.01371 (17)	0.00182 (11)	0.00009 (11)	0.00032 (11)
C1	0.0317 (9)	0.0242 (7)	0.0158 (7)	0.0027 (6)	0.0009 (6)	0.0004 (6)
C2	0.0277 (9)	0.0389 (9)	0.0232 (8)	−0.0011 (7)	0.0058 (7)	−0.0017 (7)
C3	0.0239 (9)	0.0516 (11)	0.0274 (8)	0.0131 (8)	−0.0004 (7)	0.0010 (8)
C4	0.0250 (9)	0.0467 (10)	0.0213 (8)	0.0020 (7)	−0.0039 (6)	−0.0009 (7)
C5	0.0233 (7)	0.0267 (7)	0.0137 (6)	0.0007 (6)	−0.0009 (6)	−0.0011 (6)
C6	0.0361 (9)	0.0243 (7)	0.0164 (7)	0.0041 (7)	0.0003 (6)	−0.0009 (6)
C7	0.0554 (13)	0.0336 (9)	0.0292 (9)	0.0186 (9)	0.0036 (9)	0.0067 (8)
C8	0.0438 (11)	0.0246 (8)	0.0296 (9)	−0.0059 (7)	0.0065 (8)	0.0010 (7)
C9	0.0349 (9)	0.0297 (8)	0.0239 (8)	−0.0043 (7)	−0.0014 (7)	−0.0066 (7)
C10	0.0303 (9)	0.0308 (8)	0.0222 (8)	−0.0032 (7)	0.0047 (6)	0.0028 (7)
C11	0.0298 (8)	0.0283 (7)	0.0160 (7)	−0.0005 (6)	0.0006 (6)	0.0003 (6)
O1	0.0444 (7)	0.0296 (6)	0.0148 (5)	0.0054 (5)	−0.0070 (5)	−0.0027 (5)
O2	0.0362 (7)	0.0532 (8)	0.0239 (6)	0.0179 (6)	−0.0045 (5)	−0.0106 (6)
C12	0.0373 (10)	0.0288 (8)	0.0181 (8)	0.0048 (7)	0.0004 (6)	−0.0005 (7)
O3	0.1393 (17)	0.0298 (7)	0.0155 (6)	0.0092 (8)	−0.0021 (7)	−0.0003 (6)
O4	0.0484 (8)	0.0268 (6)	0.0185 (6)	−0.0005 (5)	0.0019 (5)	0.0024 (5)
O5	0.0289 (7)	0.0377 (6)	0.0274 (6)	0.0007 (5)	0.0016 (5)	−0.0031 (5)

Geometric parameters (Å, º) top

Co—O1ⁱ	2.0574 (12)	C5—C10	1.538 (2)
Co—O1	2.0574 (12)	C6—H6A	0.9700
Co—O5	2.0956 (14)	C6—H6B	0.9700
Co—O5ⁱ	2.0956 (14)	C7—C8	1.522 (3)
Co—O4ⁱⁱ	2.1061 (12)	C7—H7A	0.9700
Co—O4ⁱⁱⁱ	2.1061 (12)	C7—H7B	0.9700
C1—C12	1.511 (2)	C8—C9	1.532 (2)
C1—C9	1.533 (2)	C8—C10	1.534 (2)
C1—C6	1.535 (2)	C8—H8A	0.9800
C1—C2	1.540 (2)	C9—H9A	0.9700
C2—C3	1.525 (2)	C9—H9B	0.9700
C2—H2A	0.9700	C10—H10A	0.9700
C2—H2B	0.9700	C10—H10B	0.9700
C3—C7	1.516 (3)	C11—O2	1.237 (2)
C3—C4	1.533 (2)	C11—O1	1.2823 (19)
C3—H3A	0.9800	C12—O4	1.212 (2)
C4—C5	1.532 (2)	C12—O3	1.316 (2)
C4—H4A	0.9700	O3—H1	0.8083
C4—H4B	0.9700	O4—Co^iv	2.1061 (12)
C5—C11	1.530 (2)	O5—H2	0.8045
C5—C6	1.534 (2)	O5—H3	0.8128

O1ⁱ—Co—O1	180.00 (6)	C6—C5—C10	109.03 (13)
O1ⁱ—Co—O5	91.39 (5)	C5—C6—C1	110.11 (13)
O1—Co—O5	88.61 (5)	C5—C6—H6A	109.6
O1ⁱ—Co—O5ⁱ	88.61 (5)	C1—C6—H6A	109.6
O1—Co—O5ⁱ	91.39 (5)	C5—C6—H6B	109.6
O5—Co—O5ⁱ	180.00 (6)	C1—C6—H6B	109.6
O1ⁱ—Co—O4ⁱⁱ	90.51 (5)	H6A—C6—H6B	108.2
O1—Co—O4ⁱⁱ	89.49 (5)	C3—C7—C8	109.63 (14)
O5—Co—O4ⁱⁱ	88.49 (5)	C3—C7—H7A	109.7
O5ⁱ—Co—O4ⁱⁱ	91.51 (5)	C8—C7—H7A	109.7
O1ⁱ—Co—O4ⁱⁱⁱ	89.49 (5)	C3—C7—H7B	109.7
O1—Co—O4ⁱⁱⁱ	90.51 (5)	C8—C7—H7B	109.7
O5—Co—O4ⁱⁱⁱ	91.51 (5)	H7A—C7—H7B	108.2
O5ⁱ—Co—O4ⁱⁱⁱ	88.49 (5)	C7—C8—C9	109.50 (15)
O4ⁱⁱ—Co—O4ⁱⁱⁱ	180.00 (5)	C7—C8—C10	109.98 (15)
C12—C1—C9	112.81 (14)	C9—C8—C10	109.04 (14)
C12—C1—C6	109.83 (13)	C7—C8—H8A	109.4
C9—C1—C6	108.93 (14)	C9—C8—H8A	109.4
C12—C1—C2	106.41 (13)	C10—C8—H8A	109.4
C9—C1—C2	109.37 (14)	C8—C9—C1	109.59 (13)
C6—C1—C2	109.42 (14)	C8—C9—H9A	109.8
C3—C2—C1	109.17 (13)	C1—C9—H9A	109.8
C3—C2—H2A	109.8	C8—C9—H9B	109.8
C1—C2—H2A	109.8	C1—C9—H9B	109.8
C3—C2—H2B	109.8	H9A—C9—H9B	108.2
C1—C2—H2B	109.8	C8—C10—C5	109.71 (13)
H2A—C2—H2B	108.3	C8—C10—H10A	109.7
C7—C3—C2	109.76 (15)	C5—C10—H10A	109.7
C7—C3—C4	109.50 (15)	C8—C10—H10B	109.7
C2—C3—C4	109.95 (15)	C5—C10—H10B	109.7
C7—C3—H3A	109.2	H10A—C10—H10B	108.2
C2—C3—H3A	109.2	O2—C11—O1	122.85 (15)
C4—C3—H3A	109.2	O2—C11—C5	120.66 (14)
C5—C4—C3	109.93 (13)	O1—C11—C5	116.47 (14)
C5—C4—H4A	109.7	C11—O1—Co	125.90 (11)
C3—C4—H4A	109.7	O4—C12—O3	122.98 (16)
C5—C4—H4B	109.7	O4—C12—C1	122.33 (15)
C3—C4—H4B	109.7	O3—C12—C1	114.61 (15)
H4A—C4—H4B	108.2	C12—O3—H1	111.4
C11—C5—C4	111.41 (13)	C12—O4—Co^iv	131.58 (11)
C11—C5—C6	109.66 (13)	Co—O5—H2	108.0
C4—C5—C6	109.40 (13)	Co—O5—H3	115.6
C11—C5—C10	108.90 (13)	H2—O5—H3	102.6
C4—C5—C10	108.42 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1^iv	0.81	1.82	2.6058 (19)	166
O5—H2···O2	0.80	2.07	2.7762 (18)	147
O5—H3···O2^v	0.81	2.02	2.8334 (18)	175

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₁₅O₄)₂(H₂O)₂]
M_r	541.44
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	293
a, b, c (Å)	10.718 (2), 23.638 (5), 9.0726 (18)
V (Å³)	2298.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.921, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	20865, 2622, 2145
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.086, 1.06
No. of reflections	2622
No. of parameters	161
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.30

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co—O1	2.0574 (12)	Co—O4ⁱ	2.1061 (12)
Co—O5	2.0956 (14)

Symmetry code: (i) x, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1ⁱⁱ	0.81	1.82	2.6058 (19)	166
O5—H2···O2	0.80	2.07	2.7762 (18)	147
O5—H3···O2ⁱⁱⁱ	0.81	2.02	2.8334 (18)	175

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

Acknowledgements

This project was sponsored by the K. C. Wong Magna Fund of Ningbo University and supported by the Expert Project of Key Basic Research of the Ministry of Science and Technology of China (grant No. 2003CCA00800), the Zhejiang Provincial Natural Science Foundation (grant No. Z203067) and the Ningbo Municipal Natural Science Foundation (grant No. 2006 A610061).

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