catena-Poly[[[diaqua­bis(1H-indole-3-acetato-κO)cobalt(II)]-μ-4,4′-bipyridine-κ2N:N′] tetra­hydrate]

Liu, J.-W.; Ng, S.W.

doi:10.1107/S1600536808010842

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m706-m707

doi:10.1107/S1600536808010842

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catena-Poly[[[diaquabis(1H-indole-3-acetato-κO)cobalt(II)]-μ-4,4′-bipyridine-κ²N:N′] tetrahydrate]

Ji-Wei Liu ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Chemical Technology, Daqing Petroleum Institute, Daqing 163318, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 9 April 2008; accepted 18 April 2008; online 23 April 2008)

The 4,4′-bipyridine spacer in the title compound, [Co(C₁₀H₈NO₂)₂(C₁₀H₈N₂)(H₂O)₂]·4H₂O, links the diaquacobalt(II) dicarboxylate units into a linear chain; the metal atom lies on a center of inversion in an octahedral environment. The coordinated and uncoordinated water molecules interact through O—H⋯O hydrogen bonds to form a three-dimensional network.

Related literature

For examples of diaqua transition-metal dicarboxylates that are linked by 4,4′-bipyridine, see: Deng et al. (2005 ); Gao et al. (2006 ); He et al. (2003 ); Hou et al. (2007 ); Li et al. (2006 ); Pedireddi & Varughese (2004 ); Yan et al. (2005 ); Zhang et al. (1999 ); Zheng, Su & Feng (2006 ); Zheng, Tong & Chen (2006 ).

Experimental

Crystal data

[Co(C₁₀H₈NO₂)₂(C₁₀H₈N₂)(H₂O)₂]·4H₂O
M_r = 671.56
Monoclinic, P 2₁ /c
a = 11.5011 (3) Å
b = 16.0953 (4) Å
c = 8.8302 (2) Å
β = 111.784 (1)°
V = 1517.86 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 295 (2) K
0.35 × 0.20 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.810, T_max = 0.951
11131 measured reflections
2584 independent reflections
1771 reflections with I > 2˘I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 1.03
2584 reflections
226 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—O1	2.182 (2)
Co1—O1W	2.042 (2)
Co1—N2	2.184 (2)

O1—Co1—O1W	89.74 (7)
O1—Co1—O1Wⁱ	90.26 (7)
O1—Co1—N2	91.58 (7)
O1—Co1—N2ⁱ	88.42 (7)
O1W—Co1—N2	91.63 (8)
O1W—Co1—N2ⁱ	88.37 (8)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2	0.85 (3)	1.76 (3)	2.585 (2)	165 (3)
O1W—H1W2⋯O2W	0.85 (3)	1.89 (3)	2.724 (3)	171 (3)
O2W—H2W1⋯O3Wⁱⁱ	0.85 (3)	1.89 (3)	2.735 (3)	173 (3)
O2W—H2W2⋯O2ⁱⁱⁱ	0.84 (3)	1.94 (3)	2.752 (3)	162 (3)
O3W—H3W1⋯O1	0.85 (3)	2.00 (3)	2.854 (3)	179 (3)
O3W—H3W2⋯O2Wⁱ	0.85 (3)	2.03 (3)	2.872 (3)	168 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010842/sg2234sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010842/sg2234Isup2.hkl

checkCIF report

Comment top

There are many crystallographic examples of transition metal di(carboxylates) that are linked by the 4,4'-bipyridine spacer ligand. Among these are examples that have coordinated water; the water entities engage in hydrogen bonding that consolidates the structure.

The title diaquadi(indole-3-carboxylato)cobalt–4,4'-bipyridine tetrahydrate (Scheme I) exists as a chain. The metal atom is coordinated by two unidentate carboxylate groups, two water molecules and two 4,4'-bipyridine ligands in an octahedral geometry (Fig. 1). The spacer ligand links the mononuclear units into a linear chain. The chains are further linked by hydrogen bonds into a three-dimensional network (Table 2).

Related literature top

For examples of diaqua transition-metal dicarboxylates that are linked by 4,4'-bipyridine, see: Deng et al. (2005); Gao et al. (2006); He et al. (2003); Hou et al. (2007); Li et al. (2006); Pedireddi & Varughese (2004); Yan et al. (2005); Zhang et al. (1999); Zheng, Su & Feng (2006); Zheng, Tong & Chen (2006).

Experimental top

Cobalt(II) sulfate septahydrate (0.28 g, 1 mmol) and 4,4'-bipyridine (0.16 g, 1 mmol) were added to a hot aqueous solution of indole-3-acetic acid (0.12 g, 1 mmol); the pH was adjusted to 6 with 0.1M sodium hydroxide. The solution was allowed to evaporate at room temperature. Single crystals are separated from the filtered solution after several days.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Thermal displacement ellipsoid plot (Barbour, 2001) illustrating the coordination geometry of cobalt in Co(C₁₀H₈N₂)(C₁₀H₈NO₂)₂(H₂O)₂^.4H₂O. Displacement ellipsoids are drawn at the 50% probability level and H atoms as spheres of arbitrary radii.

catena-Poly[[[diaquabis(1H-indole-3-acetato- κO)cobalt(II)]-µ-4,4'-bipyridine-κ²N:N'] tetrahydrate] top

Crystal data top

[Co(C₁₀H₈NO₂)₂(C₁₀H₈N₂)(H₂O)₂]·4H₂O	F(000) = 702
M_r = 671.56	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2534 reflections
a = 11.5011 (3) Å	θ = 2.3–21.7°
b = 16.0953 (4) Å	µ = 0.63 mm⁻¹
c = 8.8302 (2) Å	T = 295 K
β = 111.784 (1)°	Block, pink
V = 1517.86 (6) Å³	0.35 × 0.20 × 0.08 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	2584 independent reflections
Radiation source: fine-focus sealed tube	1771 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.810, T_max = 0.951	k = −17→19
11131 measured reflections	l = −10→9

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0506P)² + 0.1356P] where P = (F_o² + 2F_c²)/3
2584 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.33 e Å⁻³
10 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Co(C₁₀H₈NO₂)₂(C₁₀H₈N₂)(H₂O)₂]·4H₂O	V = 1517.86 (6) Å³
M_r = 671.56	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5011 (3) Å	µ = 0.63 mm⁻¹
b = 16.0953 (4) Å	T = 295 K
c = 8.8302 (2) Å	0.35 × 0.20 × 0.08 mm
β = 111.784 (1)°

Data collection top

Bruker APEXII diffractometer	2584 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1771 reflections with I > 2˘I)
T_min = 0.810, T_max = 0.951	R_int = 0.037
11131 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	10 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
2584 reflections	Δρ_min = −0.53 e Å⁻³
226 parameters

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

	x	y	z	U_iso*/U_eq
Co1	0.5000	0.5000	0.5000	0.02917 (19)
O1	0.57914 (16)	0.50222 (11)	0.7661 (2)	0.0353 (5)
O2	0.60753 (17)	0.63848 (12)	0.8108 (2)	0.0454 (5)
O1W	0.50557 (18)	0.62679 (12)	0.4969 (2)	0.0423 (5)
H1W1	0.539 (2)	0.6396 (16)	0.5967 (13)	0.063*
H1W2	0.472 (2)	0.6689 (12)	0.441 (3)	0.063*
O2W	0.4133 (2)	0.77242 (13)	0.3416 (3)	0.0535 (6)
H2W1	0.387 (2)	0.7955 (17)	0.409 (3)	0.080*
H2W2	0.4825 (18)	0.7928 (19)	0.348 (4)	0.080*
O3W	0.6525 (2)	0.34501 (14)	0.9218 (3)	0.0617 (6)
H3W1	0.631 (3)	0.3921 (10)	0.877 (3)	0.093*
H3W2	0.644 (3)	0.3081 (13)	0.850 (3)	0.093*
N1	0.8052 (3)	0.72774 (16)	1.3063 (3)	0.0603 (8)
H1N	0.806 (3)	0.7654 (15)	1.373 (3)	0.090*
N2	0.30936 (19)	0.50106 (13)	0.4973 (3)	0.0335 (6)
C1	0.6121 (2)	0.56454 (19)	0.8587 (3)	0.0339 (7)
C2	0.6562 (3)	0.55025 (19)	1.0415 (3)	0.0443 (8)
H2A	0.5834	0.5440	1.0709	0.053*
H2B	0.7028	0.4985	1.0676	0.053*
C3	0.7364 (3)	0.61775 (17)	1.1427 (3)	0.0374 (7)
C4	0.7058 (3)	0.6757 (2)	1.2330 (4)	0.0530 (9)
H4	0.6285	0.6796	1.2436	0.064*
C5	0.8624 (3)	0.63474 (17)	1.1623 (3)	0.0369 (7)
C6	0.9462 (3)	0.5963 (2)	1.1030 (4)	0.0522 (8)
H6	0.9216	0.5504	1.0344	0.063*
C7	1.0646 (3)	0.6275 (3)	1.1475 (5)	0.0712 (11)
H7	1.1208	0.6022	1.1088	0.085*
C8	1.1028 (3)	0.6955 (3)	1.2485 (5)	0.0776 (12)
H8	1.1842	0.7149	1.2761	0.093*
C9	1.0246 (3)	0.7352 (2)	1.3093 (4)	0.0656 (10)
H9	1.0510	0.7812	1.3771	0.079*
C10	0.9034 (3)	0.70374 (18)	1.2654 (3)	0.0460 (8)
C11	0.2700 (2)	0.55901 (17)	0.5739 (4)	0.0393 (7)
H11	0.3255	0.6011	0.6273	0.047*
C12	0.1515 (2)	0.56060 (17)	0.5789 (3)	0.0401 (7)
H12	0.1300	0.6025	0.6362	0.048*
C13	0.0644 (2)	0.50028 (16)	0.4993 (3)	0.0309 (6)
C14	0.1058 (2)	0.44017 (18)	0.4190 (4)	0.0439 (8)
H14	0.0521	0.3977	0.3633	0.053*
C15	0.2258 (3)	0.44290 (18)	0.4212 (4)	0.0439 (8)
H15	0.2503	0.4014	0.3659	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0262 (3)	0.0343 (3)	0.0289 (3)	0.0001 (2)	0.0124 (2)	0.0008 (3)
O1	0.0385 (11)	0.0364 (11)	0.0311 (11)	−0.0045 (9)	0.0129 (9)	−0.0043 (10)
O2	0.0620 (14)	0.0377 (13)	0.0338 (12)	−0.0019 (11)	0.0146 (10)	0.0007 (11)
O1W	0.0498 (12)	0.0364 (12)	0.0347 (11)	0.0023 (10)	0.0088 (10)	0.0033 (10)
O2W	0.0640 (15)	0.0449 (14)	0.0537 (15)	−0.0024 (12)	0.0243 (12)	−0.0021 (11)
O3W	0.0847 (17)	0.0520 (14)	0.0557 (15)	0.0017 (15)	0.0343 (14)	0.0021 (12)
N1	0.081 (2)	0.0483 (19)	0.0477 (19)	0.0026 (17)	0.0200 (17)	−0.0148 (15)
N2	0.0311 (12)	0.0415 (14)	0.0303 (13)	−0.0024 (12)	0.0142 (10)	−0.0054 (12)
C1	0.0275 (14)	0.045 (2)	0.0317 (17)	−0.0034 (14)	0.0144 (12)	−0.0003 (17)
C2	0.0499 (18)	0.053 (2)	0.0284 (17)	−0.0093 (16)	0.0130 (14)	−0.0004 (16)
C3	0.0463 (17)	0.0416 (18)	0.0240 (16)	−0.0032 (15)	0.0125 (13)	−0.0028 (14)
C4	0.051 (2)	0.063 (2)	0.046 (2)	0.0047 (18)	0.0186 (16)	−0.0020 (18)
C5	0.0443 (17)	0.0373 (18)	0.0297 (16)	−0.0010 (15)	0.0145 (13)	0.0031 (15)
C6	0.056 (2)	0.054 (2)	0.052 (2)	−0.0043 (17)	0.0275 (17)	−0.0029 (17)
C7	0.059 (2)	0.087 (3)	0.078 (3)	−0.001 (2)	0.037 (2)	0.010 (2)
C8	0.053 (2)	0.102 (3)	0.071 (3)	−0.022 (2)	0.015 (2)	0.019 (3)
C9	0.073 (3)	0.058 (2)	0.049 (2)	−0.026 (2)	0.0027 (19)	0.0010 (19)
C10	0.059 (2)	0.0398 (19)	0.0331 (19)	−0.0060 (17)	0.0094 (16)	−0.0011 (16)
C11	0.0318 (16)	0.0437 (18)	0.0445 (19)	−0.0071 (14)	0.0166 (13)	−0.0130 (16)
C12	0.0348 (16)	0.0449 (19)	0.0467 (19)	−0.0023 (14)	0.0221 (14)	−0.0130 (15)
C13	0.0266 (14)	0.0405 (17)	0.0276 (15)	0.0003 (14)	0.0125 (11)	−0.0003 (14)
C14	0.0317 (16)	0.049 (2)	0.054 (2)	−0.0066 (14)	0.0191 (14)	−0.0151 (16)
C15	0.0361 (17)	0.052 (2)	0.049 (2)	−0.0035 (16)	0.0225 (15)	−0.0193 (17)

Geometric parameters (Å, º) top

Co1—O1	2.182 (2)	C3—C4	1.355 (4)
Co1—O1ⁱ	2.182 (2)	C3—C5	1.421 (3)
Co1—O1Wⁱ	2.042 (2)	C4—H4	0.9300
Co1—O1W	2.042 (2)	C5—C6	1.400 (4)
Co1—N2	2.184 (2)	C5—C10	1.402 (4)
Co1—N2ⁱ	2.184 (2)	C6—C7	1.365 (4)
O1—C1	1.260 (3)	C6—H6	0.9300
O2—C1	1.258 (3)	C7—C8	1.376 (5)
O1W—H1W1	0.85 (3)	C7—H7	0.9300
O1W—H1W2	0.85 (3)	C8—C9	1.365 (5)
O2W—H2W1	0.85 (3)	C8—H8	0.9300
O2W—H2W2	0.84 (3)	C9—C10	1.396 (4)
O3W—H3W1	0.85 (3)	C9—H9	0.9300
O3W—H3W2	0.85 (3)	C11—C12	1.380 (3)
N1—C10	1.364 (4)	C11—H11	0.9300
N1—C4	1.371 (4)	C12—C13	1.385 (3)
N1—H1N	0.84 (1)	C12—H12	0.9300
N2—C11	1.327 (3)	C13—C14	1.384 (3)
N2—C15	1.331 (3)	C13—C13ⁱⁱ	1.487 (5)
C1—C2	1.519 (4)	C14—C15	1.374 (3)
C2—C3	1.489 (4)	C14—H14	0.9300
C2—H2A	0.9700	C15—H15	0.9300
C2—H2B	0.9700

O1—Co1—O1ⁱ	180.0	N1—C4—H4	124.9
O1—Co1—O1W	89.74 (7)	C6—C5—C10	118.7 (3)
O1—Co1—O1Wⁱ	90.26 (7)	C6—C5—C3	133.0 (3)
O1—Co1—N2	91.58 (7)	C10—C5—C3	108.3 (2)
O1—Co1—N2ⁱ	88.42 (7)	C7—C6—C5	118.8 (3)
O1W—Co1—O1Wⁱ	180.0	C7—C6—H6	120.6
O1W—Co1—N2	91.63 (8)	C5—C6—H6	120.6
O1W—Co1—N2ⁱ	88.37 (8)	C6—C7—C8	121.6 (3)
N2—Co1—N2ⁱ	180.0	C6—C7—H7	119.2
C1—O1—Co1	128.05 (17)	C8—C7—H7	119.2
Co1—O1W—H1W1	104 (2)	C9—C8—C7	121.9 (3)
Co1—O1W—H1W2	143 (2)	C9—C8—H8	119.1
H1W1—O1W—H1W2	111 (2)	C7—C8—H8	119.1
H2W1—O2W—H2W2	111 (2)	C8—C9—C10	117.2 (3)
H3W1—O3W—H3W2	110 (2)	C8—C9—H9	121.4
C10—N1—C4	109.2 (3)	C10—C9—H9	121.4
C10—N1—H1N	127 (3)	N1—C10—C9	131.6 (3)
C4—N1—H1N	124 (3)	N1—C10—C5	106.5 (3)
C11—N2—C15	115.6 (2)	C9—C10—C5	121.9 (3)
C11—N2—Co1	122.10 (17)	N2—C11—C12	123.9 (2)
C15—N2—Co1	122.25 (17)	N2—C11—H11	118.1
O2—C1—O1	124.7 (3)	C12—C11—H11	118.1
O2—C1—C2	117.2 (3)	C11—C12—C13	120.5 (2)
O1—C1—C2	118.1 (2)	C11—C12—H12	119.7
C3—C2—C1	114.6 (2)	C13—C12—H12	119.7
C3—C2—H2A	108.6	C14—C13—C12	115.4 (2)
C1—C2—H2A	108.6	C14—C13—C13ⁱⁱ	122.2 (3)
C3—C2—H2B	108.6	C12—C13—C13ⁱⁱ	122.4 (3)
C1—C2—H2B	108.6	C15—C14—C13	120.3 (3)
H2A—C2—H2B	107.6	C15—C14—H14	119.8
C4—C3—C5	105.8 (3)	C13—C14—H14	119.8
C4—C3—C2	128.1 (3)	N2—C15—C14	124.2 (3)
C5—C3—C2	126.1 (2)	N2—C15—H15	117.9
C3—C4—N1	110.2 (3)	C14—C15—H15	117.9
C3—C4—H4	124.9

O1Wⁱ—Co1—O1—C1	178.5 (2)	C2—C3—C5—C10	179.3 (3)
O1W—Co1—O1—C1	−1.5 (2)	C10—C5—C6—C7	−0.1 (4)
N2—Co1—O1—C1	−93.1 (2)	C3—C5—C6—C7	−178.7 (3)
N2ⁱ—Co1—O1—C1	86.9 (2)	C5—C6—C7—C8	−0.2 (5)
O1Wⁱ—Co1—N2—C11	144.9 (2)	C6—C7—C8—C9	0.1 (6)
O1W—Co1—N2—C11	−35.1 (2)	C7—C8—C9—C10	0.2 (5)
O1—Co1—N2—C11	54.6 (2)	C4—N1—C10—C9	−179.1 (3)
O1ⁱ—Co1—N2—C11	−125.4 (2)	C4—N1—C10—C5	0.4 (3)
O1Wⁱ—Co1—N2—C15	−34.0 (2)	C8—C9—C10—N1	178.9 (3)
O1W—Co1—N2—C15	146.0 (2)	C8—C9—C10—C5	−0.5 (5)
O1—Co1—N2—C15	−124.2 (2)	C6—C5—C10—N1	−179.2 (3)
O1ⁱ—Co1—N2—C15	55.8 (2)	C3—C5—C10—N1	−0.2 (3)
Co1—O1—C1—O2	−2.0 (4)	C6—C5—C10—C9	0.4 (4)
Co1—O1—C1—C2	175.64 (15)	C3—C5—C10—C9	179.4 (3)
O2—C1—C2—C3	−24.1 (3)	C15—N2—C11—C12	0.7 (4)
O1—C1—C2—C3	158.1 (2)	Co1—N2—C11—C12	−178.1 (2)
C1—C2—C3—C4	106.8 (3)	N2—C11—C12—C13	−1.0 (4)
C1—C2—C3—C5	−72.4 (4)	C11—C12—C13—C14	0.6 (4)
C5—C3—C4—N1	0.4 (3)	C11—C12—C13—C13ⁱⁱ	−179.7 (3)
C2—C3—C4—N1	−179.0 (3)	C12—C13—C14—C15	−0.2 (4)
C10—N1—C4—C3	−0.5 (4)	C13ⁱⁱ—C13—C14—C15	−179.8 (3)
C4—C3—C5—C6	178.7 (3)	C11—N2—C15—C14	−0.2 (4)
C2—C3—C5—C6	−2.0 (5)	Co1—N2—C15—C14	178.7 (2)
C4—C3—C5—C10	−0.1 (3)	C13—C14—C15—N2	−0.1 (5)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −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···O2	0.85 (3)	1.76 (3)	2.585 (2)	165 (3)
O1W—H1W2···O2W	0.85 (3)	1.89 (3)	2.724 (3)	171 (3)
O2W—H2W1···O3Wⁱⁱⁱ	0.85 (3)	1.89 (3)	2.735 (3)	173 (3)
O2W—H2W2···O2^iv	0.84 (3)	1.94 (3)	2.752 (3)	162 (3)
O3W—H3W1···O1	0.85 (3)	2.00 (3)	2.854 (3)	179 (3)
O3W—H3W2···O2Wⁱ	0.85 (3)	2.03 (3)	2.872 (3)	168 (3)
N1—H1N···O2^v	0.84 (1)	2.64 (3)	3.142 (3)	120 (3)

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₈NO₂)₂(C₁₀H₈N₂)(H₂O)₂]·4H₂O
M_r	671.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.5011 (3), 16.0953 (4), 8.8302 (2)
β (°)	111.784 (1)
V (Å³)	1517.86 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.35 × 0.20 × 0.08

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.810, 0.951
No. of measured, independent and observed [I > 2˘I)] reflections	11131, 2584, 1771
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 1.03
No. of reflections	2584
No. of parameters	226
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.53

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).

Selected geometric parameters (Å, º) top

Co1—O1	2.182 (2)	Co1—N2	2.184 (2)
Co1—O1W	2.042 (2)

O1—Co1—O1W	89.74 (7)	O1—Co1—N2ⁱ	88.42 (7)
O1—Co1—O1Wⁱ	90.26 (7)	O1W—Co1—N2	91.63 (8)
O1—Co1—N2	91.58 (7)	O1W—Co1—N2ⁱ	88.37 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.85 (3)	1.76 (3)	2.585 (2)	165 (3)
O1W—H1W2···O2W	0.85 (3)	1.89 (3)	2.724 (3)	171 (3)
O2W—H2W1···O3Wⁱⁱ	0.85 (3)	1.89 (3)	2.735 (3)	173 (3)
O2W—H2W2···O2ⁱⁱⁱ	0.84 (3)	1.94 (3)	2.752 (3)	162 (3)
O3W—H3W1···O1	0.85 (3)	2.00 (3)	2.854 (3)	179 (3)
O3W—H3W2···O2Wⁱ	0.85 (3)	2.03 (3)	2.872 (3)	168 (3)

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

Acknowledgements

We thank Daqing Petroleum Institute and the University of Malaya for generously supporting this study.

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