catena-Poly[[[tetra­aqua­cobalt(II)]-μ-4,4′-bipyridine-κ2N:N′] 2-[4-(2-carboxyl­ato­eth­yl)phen­oxy]acetate]

Wang, X.-F.; Liu, C.-B.; Huang, D.-H.; Xiong, Z.-Q.

doi:10.1107/S1600536809021552

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m764-m765

doi:10.1107/S1600536809021552

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catena-Poly[[[tetraaquacobalt(II)]-μ-4,4′-bipyridine-κ²N:N′] 2-[4-(2-carboxylatoethyl)phenoxy]acetate]

Xi-Fang Wang,^a Chong-Bo Liu,^a ^* De-He Huang ^a and Zhi-Qiang Xiong ^b

^aSchool of Environment and Chemical Engineering, Nanchang Hangkong University, Nanchang 330063, People's Republic of China, and ^bInstrumental Analysis Center, Nanchang Hangkong University, Nanchang 330063, People's Republic of China
^*Correspondence e-mail: cbliu2002@163.com

(Received 31 May 2009; accepted 6 June 2009; online 13 June 2009)

In the title complex, {[Co(C₁₀H₈N₂)(H₂O)₄](C₁₁H₁₀O₅)}_n, the unique Co^II ion lies on an inversion center and is coordinated by two N atoms from two 4,4′-bipyridine ligands and four O atoms from four water molecules in a slightly distorted octahedral coordination geometry. The 4,4′-bipyridine ligands bridge Co^II ions into a one-dimensional chain structure. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link cations and anions into a three-dimensional network. The dianions are completely disordered about an inversion center.

Related literature

For background to assembly of high-dimensional supramolecular coordination polymers, see: Ye et al. (2005 ). For 3-(4-hydroxyphenyl)propanoic acid as a potential multidentate ligand and a good donor and acceptor of hydrogen bonds, see: Tan et al. (2007 ). 4,4′-Bipyridine is widely used as a spacer in the construction of supramolecular architectures, see: Tao et al. (2000 ); Cussen et al. (2002 ). For the analogous one-dimensional structure with a 3-carboxylatophenoxyacetate dianion, see: Zhao et al. (2005 ).

Experimental

Crystal data

[Co(C₁₀H₈N₂)(H₂O)₄](C₁₁H₁₀O₅)
M_r = 509.37
Triclinic, $[P \overline 1]$
a = 7.1311 (10) Å
b = 7.6319 (10) Å
c = 10.4978 (14) Å
α = 91.930 (1)°
β = 101.832 (1)°
γ = 94.002 (1)°
V = 557.15 (13) Å³
Z = 1
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 291 K
0.50 × 0.41 × 0.21 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.674, T_max = 0.845
4108 measured reflections
2036 independent reflections
2008 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.085
S = 1.06
2036 reflections
176 parameters
364 restraints
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—O1	2.0840 (16)
Co1—O2	2.1083 (16)
Co1—N1	2.1530 (17)

O1ⁱ—Co1—O1	180
O1—Co1—O2ⁱ	88.34 (7)
O1—Co1—O2	91.66 (7)
O2ⁱ—Co1—O2	180
O1—Co1—N1	91.93 (7)
O2—Co1—N1	90.36 (7)
O1—Co1—N1ⁱ	88.07 (7)
O2—Co1—N1ⁱ	89.63 (7)
N1—Co1—N1ⁱ	180
Symmetry code: (i) -x, -y, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H4W⋯O4′ⁱⁱ	0.83	2.00	2.796 (10)	161
O2—H4W⋯O4ⁱⁱ	0.83	1.86	2.667 (10)	165
O2—H3W⋯O4ⁱⁱⁱ	0.83	1.96	2.765 (14)	163
O2—H3W⋯O4′ⁱⁱⁱ	0.83	1.86	2.678 (14)	170
O1—H2W⋯O3^iv	0.82	2.07	2.868 (16)	164
O1—H2W⋯O3′^iv	0.82	1.90	2.691 (16)	161
O1—H1W⋯O3^v	0.83	1.97	2.789 (13)	169
O1—H1W⋯O3′^v	0.83	1.79	2.612 (14)	174
Symmetry codes: (ii) -x+1, -y, -z+1; (iii) x, y, z-1; (iv) -x+1, -y+1, -z+1; (v) x-1, y, z-1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 global, I. DOI: 10.1107/S1600536809021552/lh2836sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021552/lh2836Isup2.hkl

checkCIF report

Comment top

In recent years, assembly of high-dimensional supramolecular coordination polymers via coordination bonds, hydrogen bonds, and π···π stacks (Ye et al., 2005) have received much attention and carboxylic acid compounds as good donors and acceptors of hydrogen bonds have been widely utilized as ligands. 3-(4-hydroxyphenyl)propanoic acid (Tan et al., 2007) a pseudo-symmetric carboxylate acid is a potential multidentate ligand and a good donor and acceptor of hydrogen bonds, but its coordination polymers are less investigated. 4,4'-bipyridine is a neutral linear bifunctional ligand that is widely used as an excellent spacer in the construction of supramolecular architectures (Cussen et al., 2002; Tao et al., 2000). Here, we report the synthesis and crystals structure of a cobalt supramolecular complex formed using with 4,4'-bipyridine and 3-(4-(carboxymethoxy)phenyl)propanoic acid.

The asymmetric unit and some symmetry related atoms are shown in Fig. 1. The unique Co^II ion lies on an invesion center and is coordinated by two nitrogen atoms from two 4,4'-bipyridine ligands and four oxygen atoms from four water molecules in a slightly distorted octahedral coordination geometry. The molecules of 3-(4-(carboxymethoxy)phenyl)propanoic acid are completely deprotonated but remain uncoordinated, and the 4,4'-bipyridine ligands act as bridging to join the Co^II ions into a one-dimensional chain structure, which is further linked to a 3-D network through intermolecular O—H···O hydrogen bonds.

Related literature top

For background to assembly of high-dimensional supramolecular coordination polymers, see: Ye et al. (2005). For 3-(4-hydroxyphenyl)propanoic acid as a potential multidentate ligand and a good donor and acceptor of hydrogen bonds, see: Tan et al. (2007). 4,4'-Bipyridine is widely used as a spacer in the construction of supramolecular architectures, see: Tao et al. (2000); Cussen et al. (2002). For the analogous one-dimensional structure with a 3-carboxylatophenoxyacetate dianion, see: Zhao et al. (2005).

Experimental top

A mixture of CoCl₂.2H₂O (0.1 mmol), 4,4'-bipyridine (0.1 mmol), 3-(4-(carboxymethoxy)phenyl)propanoic acid (0.1 mmol) and 10 ml water was placed in a tube and heated at 363 K for 6 h, then cooled to room temperature. Upon cooling to RT, a few red crystals were obtained. Anal. Calcd for C21H26N2O9Co (509.37): C, 49.47; H, 5.10; N, 5.50%; Found: C, 49.23; H, 4.98; N, 5.19%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. : Part of the title complex (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and most H atoms are omitted for clarity. Primed atoms indicate one of the disorder components. [Symmetry codes: (A) -x, -y, -z; (B) 1 - x, -y, 1 - z; (C) 1 + x, -1 + y, z.]

catena-Poly[[[tetraaquacobalt(II)]-µ-4,4'-bipyridine- κ²N:N'] 2-[4-(2-carboxylatoethyl)phenoxy]acetate] top

Crystal data top

[Co(C₁₀H₈N₂)(H₂O)₄](C₁₁H₁₀O₅)	Z = 1
M_r = 509.37	F(000) = 265
Triclinic, P1	D_x = 1.518 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1311 (10) Å	Cell parameters from 3868 reflections
b = 7.6319 (10) Å	θ = 2.7–28.2°
c = 10.4978 (14) Å	µ = 0.83 mm⁻¹
α = 91.930 (1)°	T = 291 K
β = 101.832 (1)°	Block, red
γ = 94.002 (1)°	0.50 × 0.41 × 0.21 mm
V = 557.15 (13) Å³

Data collection top

Bruker SMART CCD diffractometer	2036 independent reflections
Radiation source: fine-focus sealed tube	2008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.674, T_max = 0.845	k = −9→9
4108 measured reflections	l = −12→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0304P)² + 0.7695P] where P = (F_o² + 2F_c²)/3
2036 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.61 e Å⁻³
364 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Co(C₁₀H₈N₂)(H₂O)₄](C₁₁H₁₀O₅)	γ = 94.002 (1)°
M_r = 509.37	V = 557.15 (13) Å³
Triclinic, P1	Z = 1
a = 7.1311 (10) Å	Mo Kα radiation
b = 7.6319 (10) Å	µ = 0.83 mm⁻¹
c = 10.4978 (14) Å	T = 291 K
α = 91.930 (1)°	0.50 × 0.41 × 0.21 mm
β = 101.832 (1)°

Data collection top

Bruker SMART CCD diffractometer	2036 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2008 reflections with I > 2σ(I)
T_min = 0.674, T_max = 0.845	R_int = 0.011
4108 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	364 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.06	Δρ_max = 0.61 e Å⁻³
2036 reflections	Δρ_min = −0.63 e Å⁻³
176 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	Occ. (<1)
O3	0.7094 (13)	0.448 (3)	0.8766 (14)	0.0419 (15)	0.50
O4	0.522 (2)	0.2444 (14)	0.9494 (9)	0.0368 (16)	0.50
C8	0.3511 (11)	0.4124 (10)	0.6667 (8)	0.0635 (11)	0.50
H8A	0.4539	0.4806	0.6385	0.076*	0.50
H8B	0.3700	0.2890	0.6533	0.076*	0.50
C6	0.5492 (16)	0.370 (3)	0.879 (3)	0.0363 (9)	0.50
C7	0.3670 (11)	0.4520 (12)	0.8095 (7)	0.0522 (14)	0.50
H7A	0.2547	0.4010	0.8376	0.063*	0.50
H7B	0.3781	0.5780	0.8285	0.063*	0.50
C9	0.1644 (19)	0.451 (2)	0.5829 (11)	0.0583 (13)	0.50
C10	0.1182 (18)	0.3869 (16)	0.4541 (10)	0.0612 (15)	0.50
H10	0.1933	0.3074	0.4232	0.073*	0.50
C11	0.0411 (14)	0.5566 (15)	0.6274 (14)	0.0575 (17)	0.50
H11	0.0658	0.5913	0.7154	0.069*	0.50
O3'	0.7312 (13)	0.450 (3)	0.9043 (14)	0.0419 (15)	0.50
O4'	0.513 (2)	0.2290 (14)	0.9156 (9)	0.0368 (16)	0.50
C6'	0.5648 (17)	0.374 (3)	0.876 (3)	0.0363 (9)	0.50
C7'	0.4168 (11)	0.4553 (12)	0.7713 (8)	0.0522 (14)	0.50
H7'1	0.3503	0.5373	0.8153	0.063*	0.50
H7'2	0.4868	0.5234	0.7173	0.063*	0.50
O5	0.2825 (7)	0.3461 (6)	0.6915 (5)	0.0635 (11)	0.50
C9'	0.1435 (18)	0.435 (2)	0.5964 (11)	0.0583 (13)	0.50
C10'	0.1492 (18)	0.4241 (16)	0.4648 (9)	0.0612 (15)	0.50
H10'	0.2554	0.3795	0.4403	0.073*	0.50
C11'	−0.0013 (14)	0.5223 (14)	0.6328 (14)	0.0575 (17)	0.50
H11'	−0.0012	0.5453	0.7204	0.069*	0.50
Co1	0.0000	0.0000	0.0000	0.02210 (13)
O1	0.0283 (2)	0.2722 (2)	−0.01206 (18)	0.0396 (4)
H1W	−0.0701	0.3243	−0.0349	0.059*
H2W	0.1207	0.3397	0.0241	0.059*
O2	0.2400 (2)	−0.0305 (2)	−0.08486 (16)	0.0338 (4)
H3W	0.3136	0.0561	−0.0905	0.051*
H4W	0.2965	−0.1087	−0.0441	0.051*
N1	0.1824 (3)	0.0139 (3)	0.19142 (17)	0.0288 (4)
C1	0.3560 (3)	0.1002 (3)	0.2175 (2)	0.0341 (5)
H1	0.3934	0.1655	0.1524	0.041*
C2	0.4835 (3)	0.0981 (3)	0.3358 (2)	0.0356 (6)
H2	0.6033	0.1601	0.3483	0.043*
C3	0.4332 (3)	0.0036 (3)	0.4357 (2)	0.0285 (5)
C4	0.2514 (4)	−0.0850 (5)	0.4090 (3)	0.0557 (9)
H4	0.2096	−0.1502	0.4726	0.067*
C5	0.1325 (4)	−0.0761 (4)	0.2877 (3)	0.0532 (8)
H5	0.0114	−0.1361	0.2725	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0288 (17)	0.0355 (10)	0.050 (5)	−0.0043 (18)	−0.0169 (18)	0.009 (3)
O4	0.0306 (14)	0.0374 (17)	0.038 (4)	0.0015 (14)	−0.005 (3)	0.010 (3)
C8	0.053 (2)	0.056 (2)	0.067 (2)	0.0142 (17)	−0.0250 (18)	0.0040 (18)
C6	0.0301 (17)	0.0288 (13)	0.0428 (15)	0.0016 (14)	−0.0095 (18)	0.0037 (10)
C7	0.044 (3)	0.0434 (16)	0.059 (3)	0.006 (2)	−0.016 (2)	0.011 (2)
C9	0.044 (2)	0.058 (2)	0.065 (2)	0.0198 (19)	−0.0110 (16)	−0.0018 (17)
C10	0.042 (3)	0.063 (3)	0.072 (2)	0.020 (3)	−0.0052 (19)	−0.016 (2)
C11	0.047 (3)	0.063 (3)	0.059 (2)	0.010 (3)	0.001 (2)	−0.001 (2)
O3'	0.0288 (17)	0.0355 (10)	0.050 (5)	−0.0043 (18)	−0.0169 (18)	0.009 (3)
O4'	0.0306 (14)	0.0374 (17)	0.038 (4)	0.0015 (14)	−0.005 (3)	0.010 (3)
C6'	0.0301 (17)	0.0288 (13)	0.0428 (15)	0.0016 (14)	−0.0095 (18)	0.0037 (10)
C7'	0.044 (3)	0.0434 (16)	0.059 (3)	0.006 (2)	−0.016 (2)	0.011 (2)
O5	0.053 (2)	0.056 (2)	0.067 (2)	0.0142 (17)	−0.0250 (18)	0.0040 (18)
C9'	0.044 (2)	0.058 (2)	0.065 (2)	0.0198 (19)	−0.0110 (16)	−0.0018 (17)
C10'	0.042 (3)	0.063 (3)	0.072 (2)	0.020 (3)	−0.0052 (19)	−0.016 (2)
C11'	0.047 (3)	0.063 (3)	0.059 (2)	0.010 (3)	0.001 (2)	−0.001 (2)
Co1	0.0185 (2)	0.0246 (2)	0.0200 (2)	0.00069 (15)	−0.00368 (15)	0.00413 (15)
O1	0.0309 (9)	0.0260 (8)	0.0538 (11)	−0.0002 (7)	−0.0092 (8)	0.0043 (8)
O2	0.0249 (8)	0.0398 (9)	0.0356 (9)	0.0033 (7)	0.0029 (7)	0.0085 (7)
N1	0.0246 (9)	0.0354 (10)	0.0226 (9)	0.0004 (8)	−0.0041 (7)	0.0048 (8)
C1	0.0307 (12)	0.0427 (14)	0.0248 (11)	−0.0057 (10)	−0.0024 (9)	0.0090 (10)
C2	0.0279 (12)	0.0450 (14)	0.0281 (12)	−0.0084 (10)	−0.0052 (9)	0.0073 (10)
C3	0.0280 (11)	0.0307 (11)	0.0229 (11)	0.0029 (9)	−0.0044 (9)	0.0025 (9)
C4	0.0417 (15)	0.084 (2)	0.0310 (14)	−0.0249 (15)	−0.0109 (11)	0.0275 (14)
C5	0.0352 (14)	0.079 (2)	0.0348 (14)	−0.0234 (14)	−0.0105 (11)	0.0218 (14)

Geometric parameters (Å, º) top

O3—C6	1.257 (6)	C10'—H10'	0.9300
O4—C6	1.257 (6)	C11'—C10'ⁱ	1.41 (2)
C8—C9	1.491 (13)	C11'—H11'	0.9300
C8—C7	1.499 (11)	Co1—O1ⁱⁱ	2.0840 (16)
C8—H8A	0.9700	Co1—O1	2.0840 (16)
C8—H8B	0.9700	Co1—O2ⁱⁱ	2.1083 (16)
C6—C7	1.540 (8)	Co1—O2	2.1083 (16)
C7—H7A	0.9700	Co1—N1	2.1530 (17)
C7—H7B	0.9700	Co1—N1ⁱⁱ	2.1531 (17)
C9—C11	1.375 (6)	O1—H1W	0.8271
C9—C10	1.387 (7)	O1—H2W	0.8245
C10—C11ⁱ	1.379 (19)	O2—H3W	0.8262
C10—H10	0.9300	O2—H4W	0.8251
C11—C10ⁱ	1.379 (19)	N1—C1	1.333 (3)
C11—H11	0.9300	N1—C5	1.334 (3)
O3'—C6'	1.258 (6)	C1—C2	1.382 (3)
O4'—C6'	1.255 (6)	C1—H1	0.9300
C6'—C7'	1.537 (7)	C2—C3	1.385 (3)
C7'—O5	1.352 (10)	C2—H2	0.9300
C7'—H7'1	0.9700	C3—C4	1.390 (3)
C7'—H7'2	0.9700	C3—C3ⁱⁱⁱ	1.489 (4)
O5—C9'	1.475 (13)	C4—C5	1.384 (3)
C9'—C11'	1.377 (6)	C4—H4	0.9300
C9'—C10'	1.391 (7)	C5—H5	0.9300
C10'—C11'ⁱ	1.41 (2)

C9—C8—C7	114.6 (7)	C9'—C11'—H11'	120.6
C9—C8—H8A	108.6	C10'ⁱ—C11'—H11'	120.6
C7—C8—H8A	108.6	O1ⁱⁱ—Co1—O1	180
C9—C8—H8B	108.6	O1ⁱⁱ—Co1—O2ⁱⁱ	91.66 (7)
C7—C8—H8B	108.6	O1—Co1—O2ⁱⁱ	88.34 (7)
H8A—C8—H8B	107.6	O1ⁱⁱ—Co1—O2	88.33 (7)
O3—C6—O4	125.4 (9)	O1—Co1—O2	91.66 (7)
O3—C6—C7	118.0 (7)	O2ⁱⁱ—Co1—O2	180
O4—C6—C7	115.7 (8)	O1ⁱⁱ—Co1—N1	88.07 (7)
C8—C7—C6	106.0 (13)	O1—Co1—N1	91.93 (7)
C8—C7—H7A	110.5	O2ⁱⁱ—Co1—N1	89.64 (7)
C6—C7—H7A	110.5	O2—Co1—N1	90.36 (7)
C8—C7—H7B	110.5	O1ⁱⁱ—Co1—N1ⁱⁱ	91.93 (7)
C6—C7—H7B	110.5	O1—Co1—N1ⁱⁱ	88.07 (7)
H7A—C7—H7B	108.7	O2ⁱⁱ—Co1—N1ⁱⁱ	90.36 (7)
C11—C9—C10	118.6 (7)	O2—Co1—N1ⁱⁱ	89.63 (7)
C11—C9—C8	121.7 (6)	N1—Co1—N1ⁱⁱ	180
C10—C9—C8	119.5 (5)	Co1—O1—H1W	118.4
C11ⁱ—C10—C9	119.0 (12)	Co1—O1—H2W	126.8
C11ⁱ—C10—H10	120.5	H1W—O1—H2W	112.0
C9—C10—H10	120.5	Co1—O2—H3W	119.7
C9—C11—C10ⁱ	122.2 (12)	Co1—O2—H4W	104.4
C9—C11—H11	118.9	H3W—O2—H4W	112.1
C10ⁱ—C11—H11	118.9	C1—N1—C5	116.50 (19)
O4'—C6'—O3'	125.8 (9)	C1—N1—Co1	122.27 (15)
O4'—C6'—C7'	116.6 (7)	C5—N1—Co1	121.02 (16)
O3'—C6'—C7'	117.2 (6)	N1—C1—C2	123.7 (2)
O5—C7'—C6'	118.2 (10)	N1—C1—H1	118.2
O5—C7'—H7'1	107.8	C2—C1—H1	118.2
C6'—C7'—H7'1	107.8	C1—C2—C3	120.1 (2)
O5—C7'—H7'2	107.8	C1—C2—H2	119.9
C6'—C7'—H7'2	107.8	C3—C2—H2	119.9
H7'1—C7'—H7'2	107.1	C2—C3—C4	116.2 (2)
C7'—O5—C9'	114.6 (8)	C2—C3—C3ⁱⁱⁱ	121.9 (3)
C11'—C9'—C10'	117.9 (7)	C4—C3—C3ⁱⁱⁱ	121.9 (3)
C11'—C9'—O5	121.8 (6)	C5—C4—C3	120.0 (2)
C10'—C9'—O5	120.2 (6)	C5—C4—H4	120.0
C9'—C10'—C11'ⁱ	122.8 (12)	C3—C4—H4	120.0
C9'—C10'—H10'	118.6	N1—C5—C4	123.5 (2)
C11'ⁱ—C10'—H10'	118.6	N1—C5—H5	118.2
C9'—C11'—C10'ⁱ	118.8 (12)	C4—C5—H5	118.2

C9—C8—C7—C6	168.9 (10)	O1—Co1—N1—C1	−51.9 (2)
O3—C6—C7—C8	76 (3)	O2ⁱⁱ—Co1—N1—C1	−140.20 (19)
O4—C6—C7—C8	−114 (2)	O2—Co1—N1—C1	39.80 (19)
C7—C8—C9—C11	17.1 (18)	N1ⁱⁱ—Co1—N1—C1	66 (3)
C7—C8—C9—C10	−167.0 (13)	O1ⁱⁱ—Co1—N1—C5	−46.4 (2)
C11—C9—C10—C11ⁱ	5 (2)	O1—Co1—N1—C5	133.6 (2)
C8—C9—C10—C11ⁱ	−170.8 (13)	O2ⁱⁱ—Co1—N1—C5	45.3 (2)
C10—C9—C11—C10ⁱ	−5 (2)	O2—Co1—N1—C5	−134.7 (2)
C8—C9—C11—C10ⁱ	170.5 (13)	N1ⁱⁱ—Co1—N1—C5	−109 (3)
O4'—C6'—C7'—O5	−27 (3)	C5—N1—C1—C2	1.0 (4)
O3'—C6'—C7'—O5	146 (2)	Co1—N1—C1—C2	−173.7 (2)
C6'—C7'—O5—C9'	178.6 (13)	N1—C1—C2—C3	−0.5 (4)
C7'—O5—C9'—C11'	−74.6 (15)	C1—C2—C3—C4	−0.2 (4)
C7'—O5—C9'—C10'	109.2 (15)	C1—C2—C3—C3ⁱⁱⁱ	179.5 (3)
C11'—C9'—C10'—C11'ⁱ	−8 (2)	C2—C3—C4—C5	0.3 (5)
O5—C9'—C10'—C11'ⁱ	168.0 (12)	C3ⁱⁱⁱ—C3—C4—C5	−179.4 (3)
C10'—C9'—C11'—C10'ⁱ	8 (2)	C1—N1—C5—C4	−0.9 (5)
O5—C9'—C11'—C10'ⁱ	−168.3 (12)	Co1—N1—C5—C4	173.9 (3)
O1ⁱⁱ—Co1—N1—C1	128.1 (2)	C3—C4—C5—N1	0.3 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4W···O4′ⁱⁱⁱ	0.83	2.00	2.796 (10)	161
O2—H4W···O4ⁱⁱⁱ	0.83	1.86	2.667 (10)	165
O2—H3W···O4^iv	0.83	1.96	2.765 (14)	163
O2—H3W···O4′^iv	0.83	1.86	2.678 (14)	170
O1—H2W···O3^v	0.82	2.07	2.868 (16)	164
O1—H2W···O3′^v	0.82	1.90	2.691 (16)	161
O1—H1W···O3^vi	0.83	1.97	2.789 (13)	169
O1—H1W···O3′^vi	0.83	1.79	2.612 (14)	174

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₈N₂)(H₂O)₄](C₁₁H₁₀O₅)
M_r	509.37
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.1311 (10), 7.6319 (10), 10.4978 (14)
α, β, γ (°)	91.930 (1), 101.832 (1), 94.002 (1)
V (Å³)	557.15 (13)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.50 × 0.41 × 0.21

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.674, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	4108, 2036, 2008
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.085, 1.06
No. of reflections	2036
No. of parameters	176
No. of restraints	364
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.63

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—O1	2.0840 (16)	Co1—N1	2.1530 (17)
Co1—O2	2.1083 (16)

O1ⁱ—Co1—O1	180	O2—Co1—N1	90.36 (7)
O1—Co1—O2ⁱ	88.34 (7)	O1—Co1—N1ⁱ	88.07 (7)
O1—Co1—O2	91.66 (7)	O2—Co1—N1ⁱ	89.63 (7)
O2ⁱ—Co1—O2	180	N1—Co1—N1ⁱ	180
O1—Co1—N1	91.93 (7)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4W···O4'ⁱⁱ	0.83	2.00	2.796 (10)	161.1
O2—H4W···O4ⁱⁱ	0.83	1.86	2.667 (10)	165.4
O2—H3W···O4ⁱⁱⁱ	0.83	1.96	2.765 (14)	162.8
O2—H3W···O4'ⁱⁱⁱ	0.83	1.86	2.678 (14)	169.6
O1—H2W···O3^iv	0.82	2.07	2.868 (16)	163.7
O1—H2W···O3'^iv	0.82	1.90	2.691 (16)	160.6
O1—H1W···O3^v	0.83	1.97	2.789 (13)	168.6
O1—H1W···O3'^v	0.83	1.79	2.612 (14)	173.6

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

Acknowledgements

This work was supported by the Young Scientists Program of Jiangxi Province (grant No. 2008DQ00600) and the Natural Science Foundation of Jiangxi Province (grant No. 2008GZH0009).

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