Aqua­(oxy­diacetato-κ3O,O′,O′′)(1,10-phenanthroline-κ2N,N′)­cobalt(II) sesquihydrate

Wu, Z.-Y.; Xue, Y.-H.; Xu, D.-J.

doi:10.1107/S1600536803018762

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Aqua(oxydiacetato-κ³O,O′,O′′)(1,10-phenanthroline-κ²N,N′)cobalt(II) sesquihydrate

Z.-Y. Wu, Y.-H. Xue and D.-J. Xu

The title compound, [Co(C₄H₄O₅)(C₁₂H₈N₂)H₂O]·1.5H₂O, consists of the octahedral complex and lattice water. The asymmetric unit contains two molecules of the complex, which form a hydrogen-bonded dimer. The overlapped arrangement and shorter separations of 3.532 (6) and 3.385 (12) Å between neighboring parallel phenanthroline rings suggest the existence of π–π-stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018762/cv6227sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018762/cv6227Isup2.hkl Contains datablock I

CCDC reference: 222828

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.038
wR factor = 0.109
Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Aromatic π–π stacking interactions are important for some biological systems (Deisenhofer & Michel, 1989). As part of our investigation of the π–π stacking in metal complexes (Chen et al., 2003), the title Co^II complex, (I), was prepared.

Co^II compound (I) is isomorphous with the Ni^II (Baggio et al., 2000) and Zn^II analogues (Baggio et al., 1996). The asymmetric unit of (I) contains two molecules of the complex and three molecules of lattice water, as shown in Fig. 1. The two independent complex molecules display a similar octahedral coordination geometry (Table 1), formed by a phenanthroline (phen), a meridional oxydiacetate and a coordinated water molecule. The lattice water molecules are hydrogen bonded to the adjacent carboxyl groups (Table 2). Through the hydrogen bonding between carboxyl groups and coordinated water molecules, two independent complex molecules link to each other to form a dimer (Fig. 1). All lattice water molecules are ordered in the Co^II compound, which agrees with the case in the isomorphous Zn^II complex but differs from the disorder found in the isomorphous Ni^II complex.

The molecular packing in a unit cell is illustrated in Fig. 2. The crystal structure consists of the hydrophilic layers formed by carboxylate and water molecules and hydrophobic layers formed by phen ligands. The parallel disposition of phen ligands is observed in the crystal. Fig. 3 shows the overlapped arrangement of the neighboring parallel phen ligands. The separations of 3.532 (6) Å between N1-phen and N1ⁱⁱⁱ-phen and 3.385 (12) Å between the N3-phen and N3^iv-phen suggest the existence of aromatic π–π stacking between phen ligands.

Experimental top

An aqueous solution (10 ml) containing CoCl₂·6H₂O (0.24 g, 1 mmol) and 1,10-phenanthroline (0.18 g, 1 mmol) was mixed with another aqueous solution (10 ml) containing oxydiacetic acid hydrate (0.15 g, 1 mmol) and NaOH (0.08 g, 2 mmol) at room temperature. The mixture was refluxed for 3 h. Pink single crystals of the title compound were obtained from the filtrate after 2 weeks.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids. Dashed lines indicate hydrogen bonding.
	Fig. 2. The molecular packing diagram, showing the hydrophilic and hydrophobic layered structure. H atoms have been omitted for clarity.
	Fig. 3. A diagram showing the π–π stacking between (a) N1-phen and N1ⁱⁱⁱ-phen rings, and (b) N3-phen and N3^iv-phen rings. [Symmetry codes: (iii) 1 − x, −y, 1 − z; (iv) −x, 1 − y, 1 − z.]

Aqua(oxydiacetato-κ³O,O',O'')(1,10-phenanthroline-κ²N,N')cobalt(II) sesquihydrate top

Crystal data top

[Co(C₄H₄O₅)(C₁₂H₈N₂)(H₂O)]·1.5H₂O	F(000) = 1712
M_r = 416.25	D_x = 1.591 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16878 reflections
a = 10.4722 (16) Å	θ = 2.8–24.0°
b = 24.3161 (9) Å	µ = 1.03 mm⁻¹
c = 13.6729 (14) Å	T = 293 K
β = 93.627 (1)°	Prism, pink
V = 3474.7 (7) Å³	0.32 × 0.28 × 0.20 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	7932 independent reflections
Radiation source: fine-focus sealed tube	4856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω and ϕ scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1999)	h = −13→13
T_min = 0.715, T_max = 0.810	k = −31→30
21949 measured reflections	l = −11→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0452P)²] where P = (F_o² + 2F_c²)/3
7932 reflections	(Δ/σ)_max < 0.001
479 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Co(C₄H₄O₅)(C₁₂H₈N₂)(H₂O)]·1.5H₂O	V = 3474.7 (7) Å³
M_r = 416.25	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4722 (16) Å	µ = 1.03 mm⁻¹
b = 24.3161 (9) Å	T = 293 K
c = 13.6729 (14) Å	0.32 × 0.28 × 0.20 mm
β = 93.627 (1)°

Data collection top

Bruker SMART CCD diffractometer	7932 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1999)	4856 reflections with I > 2σ(I)
T_min = 0.715, T_max = 0.810	R_int = 0.039
21949 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 0.93	Δρ_max = 0.56 e Å⁻³
7932 reflections	Δρ_min = −0.41 e Å⁻³
479 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
Co1	0.58785 (4)	0.143260 (16)	0.36913 (3)	0.02094 (11)
Co2	0.08557 (4)	0.327209 (16)	0.41085 (3)	0.02106 (11)
O1	0.75293 (19)	0.17717 (9)	0.31909 (16)	0.0271 (5)
O2	0.8326 (2)	0.25005 (10)	0.24125 (17)	0.0383 (6)
O3	0.51880 (18)	0.20297 (8)	0.26480 (15)	0.0254 (5)
O4	0.38940 (19)	0.13530 (8)	0.36382 (15)	0.0246 (5)
O5	0.20252 (19)	0.17526 (8)	0.32204 (16)	0.0283 (5)
O6	0.58910 (18)	0.19811 (8)	0.48538 (15)	0.0259 (5)
O7	0.26493 (18)	0.29270 (8)	0.45717 (15)	0.0250 (5)
O8	0.3625 (2)	0.22534 (9)	0.54600 (16)	0.0317 (5)
O9	0.04392 (18)	0.27111 (8)	0.52297 (15)	0.0231 (5)
O10	−0.11070 (18)	0.33693 (8)	0.42756 (16)	0.0249 (5)
O11	−0.28572 (19)	0.29401 (8)	0.47351 (17)	0.0310 (5)
O12	0.06856 (19)	0.26874 (8)	0.30175 (15)	0.0251 (5)
O21	0.9841 (2)	0.11833 (9)	0.39238 (19)	0.0413 (6)
O22	0.4912 (2)	0.35695 (9)	0.4367 (2)	0.0454 (7)
O23	−0.3031 (2)	0.38823 (10)	0.29378 (19)	0.0529 (7)
N1	0.5858 (2)	0.07779 (10)	0.26708 (18)	0.0228 (6)
N2	0.6447 (2)	0.07672 (10)	0.45939 (19)	0.0223 (6)
N3	0.1406 (2)	0.39531 (10)	0.50039 (19)	0.0241 (6)
N4	0.0775 (2)	0.39248 (10)	0.30795 (19)	0.0229 (6)
C1	0.7430 (3)	0.22134 (13)	0.2693 (2)	0.0266 (7)
C2	0.6091 (3)	0.24379 (13)	0.2418 (2)	0.0282 (7)
H2A	0.5946	0.2772	0.2782	0.034*
H2B	0.6005	0.2523	0.1723	0.034*
C3	0.3908 (3)	0.22014 (12)	0.2758 (2)	0.0240 (7)
H3A	0.3487	0.2285	0.2123	0.029*
H3B	0.3898	0.2529	0.3162	0.029*
C4	0.3219 (3)	0.17305 (12)	0.3245 (2)	0.0220 (7)
C5	0.5546 (3)	0.07950 (13)	0.1721 (2)	0.0291 (8)
H5	0.5406	0.1136	0.1425	0.035*
C6	0.5415 (3)	0.03255 (13)	0.1144 (2)	0.0333 (8)
H6	0.5198	0.0355	0.0476	0.040*
C7	0.5608 (3)	−0.01806 (13)	0.1564 (3)	0.0321 (8)
H7	0.5516	−0.0498	0.1186	0.039*
C8	0.5949 (3)	−0.02162 (13)	0.2576 (2)	0.0256 (7)
C9	0.6181 (3)	−0.07232 (13)	0.3091 (3)	0.0309 (8)
H9	0.6105	−0.1054	0.2752	0.037*
C10	0.6510 (3)	−0.07274 (13)	0.4064 (3)	0.0294 (8)
H10	0.6655	−0.1061	0.4383	0.035*
C11	0.6639 (3)	−0.02276 (12)	0.4607 (2)	0.0250 (7)
C12	0.6973 (3)	−0.02059 (13)	0.5611 (2)	0.0307 (8)
H12	0.7160	−0.0528	0.5960	0.037*
C13	0.7026 (3)	0.02930 (13)	0.6080 (2)	0.0299 (8)
H13	0.7245	0.0312	0.6749	0.036*
C14	0.6749 (3)	0.07701 (13)	0.5548 (2)	0.0264 (7)
H14	0.6776	0.1105	0.5876	0.032*
C15	0.6400 (3)	0.02722 (12)	0.4124 (2)	0.0212 (7)
C16	0.6060 (3)	0.02787 (12)	0.3095 (2)	0.0218 (7)
C21	0.2662 (3)	0.25117 (13)	0.5139 (2)	0.0229 (7)
C22	0.1393 (3)	0.23028 (12)	0.5472 (2)	0.0246 (7)
H22A	0.1166	0.1959	0.5146	0.030*
H22B	0.1457	0.2239	0.6174	0.030*
C23	−0.0860 (3)	0.25229 (12)	0.5168 (2)	0.0238 (7)
H23A	−0.1135	0.2442	0.5817	0.029*
H23B	−0.0939	0.2191	0.4775	0.029*
C24	−0.1677 (3)	0.29821 (12)	0.4693 (2)	0.0227 (7)
C25	0.1743 (3)	0.39558 (14)	0.5961 (2)	0.0304 (8)
H25	0.1761	0.3623	0.6298	0.037*
C26	0.2069 (3)	0.44341 (14)	0.6480 (3)	0.0373 (9)
H26	0.2319	0.4417	0.7145	0.045*
C27	0.2018 (3)	0.49302 (14)	0.6001 (3)	0.0357 (9)
H27	0.2224	0.5253	0.6340	0.043*
C28	0.1651 (3)	0.49475 (13)	0.4990 (3)	0.0288 (8)
C29	0.1539 (3)	0.54434 (13)	0.4411 (3)	0.0376 (9)
H29	0.1718	0.5781	0.4711	0.045*
C30	0.1181 (3)	0.54294 (13)	0.3443 (3)	0.0370 (9)
H30	0.1110	0.5758	0.3095	0.044*
C31	0.0909 (3)	0.49204 (13)	0.2941 (3)	0.0298 (8)
C32	0.0530 (3)	0.48775 (14)	0.1935 (3)	0.0333 (8)
H32	0.0445	0.5192	0.1550	0.040*
C33	0.0288 (3)	0.43736 (14)	0.1533 (3)	0.0320 (8)
H33	0.0046	0.4340	0.0869	0.038*
C34	0.0409 (3)	0.39071 (13)	0.2129 (2)	0.0284 (7)
H34	0.0224	0.3566	0.1847	0.034*
C35	0.1009 (3)	0.44300 (12)	0.3480 (2)	0.0233 (7)
C36	0.1369 (3)	0.44426 (12)	0.4519 (2)	0.0246 (7)
H61	0.5164	0.2114	0.5023	0.050*
H62	0.6304	0.2312	0.4801	0.050*
H121	0.1102	0.2359	0.3080	0.050*
H122	−0.0171	0.2580	0.2812	0.050*
H211	0.9186	0.1365	0.3595	0.050*
H212	1.0633	0.1339	0.3753	0.050*
H221	0.4260	0.3321	0.4533	0.050*
H222	0.5548	0.3334	0.4434	0.050*
H231	−0.2401	0.3707	0.3237	0.050*
H232	−0.3669	0.3837	0.3303	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0195 (2)	0.0218 (2)	0.0213 (2)	0.00181 (17)	−0.00100 (17)	−0.00106 (18)
Co2	0.0193 (2)	0.0212 (2)	0.0226 (3)	−0.00098 (17)	0.00085 (17)	0.00008 (18)
O1	0.0197 (11)	0.0344 (13)	0.0271 (13)	0.0007 (10)	0.0007 (9)	−0.0007 (10)
O2	0.0254 (12)	0.0597 (16)	0.0294 (14)	−0.0163 (11)	−0.0011 (10)	0.0039 (12)
O3	0.0204 (11)	0.0247 (12)	0.0309 (13)	−0.0010 (9)	0.0002 (9)	0.0042 (10)
O4	0.0208 (11)	0.0234 (12)	0.0294 (13)	0.0004 (9)	−0.0001 (9)	0.0030 (9)
O5	0.0176 (11)	0.0289 (12)	0.0380 (14)	0.0007 (9)	−0.0006 (10)	−0.0016 (10)
O6	0.0216 (11)	0.0238 (11)	0.0327 (14)	−0.0014 (9)	0.0055 (10)	−0.0067 (10)
O7	0.0197 (11)	0.0298 (12)	0.0255 (13)	−0.0006 (9)	0.0006 (9)	−0.0013 (10)
O8	0.0246 (12)	0.0458 (14)	0.0244 (13)	0.0093 (11)	−0.0011 (10)	−0.0004 (11)
O9	0.0169 (10)	0.0243 (11)	0.0282 (13)	−0.0003 (9)	0.0018 (9)	0.0034 (9)
O10	0.0207 (11)	0.0232 (11)	0.0309 (13)	−0.0012 (9)	0.0019 (9)	0.0023 (9)
O11	0.0169 (11)	0.0306 (13)	0.0455 (15)	−0.0012 (9)	0.0013 (10)	0.0008 (11)
O12	0.0233 (11)	0.0235 (11)	0.0278 (13)	0.0016 (9)	−0.0032 (9)	−0.0029 (9)
O21	0.0307 (13)	0.0336 (14)	0.0593 (18)	−0.0010 (11)	0.0016 (12)	0.0028 (12)
O22	0.0296 (13)	0.0292 (14)	0.077 (2)	0.0002 (11)	0.0005 (13)	0.0162 (13)
O23	0.0553 (18)	0.0460 (16)	0.0553 (19)	−0.0006 (14)	−0.0119 (14)	0.0147 (14)
N1	0.0235 (14)	0.0257 (14)	0.0190 (15)	0.0031 (11)	−0.0018 (11)	−0.0033 (11)
N2	0.0217 (13)	0.0239 (14)	0.0210 (15)	0.0010 (11)	−0.0007 (11)	−0.0004 (11)
N3	0.0199 (13)	0.0244 (14)	0.0279 (16)	−0.0010 (11)	0.0008 (11)	−0.0023 (12)
N4	0.0200 (13)	0.0225 (14)	0.0266 (16)	−0.0016 (11)	0.0056 (11)	0.0000 (11)
C1	0.0247 (17)	0.039 (2)	0.0164 (18)	−0.0061 (14)	0.0009 (13)	−0.0073 (15)
C2	0.0253 (17)	0.0357 (19)	0.0232 (19)	−0.0082 (14)	−0.0004 (14)	0.0070 (15)
C3	0.0214 (16)	0.0259 (17)	0.0240 (18)	0.0042 (13)	−0.0026 (13)	0.0030 (13)
C4	0.0226 (16)	0.0235 (16)	0.0196 (17)	−0.0018 (13)	−0.0017 (13)	−0.0072 (13)
C5	0.0330 (18)	0.0273 (18)	0.027 (2)	0.0036 (15)	−0.0007 (15)	−0.0016 (14)
C6	0.039 (2)	0.039 (2)	0.0208 (19)	−0.0009 (16)	−0.0036 (15)	−0.0076 (15)
C7	0.0315 (19)	0.0280 (18)	0.037 (2)	−0.0037 (15)	0.0019 (16)	−0.0134 (16)
C8	0.0210 (16)	0.0281 (17)	0.0276 (19)	−0.0009 (13)	0.0012 (14)	−0.0049 (14)
C9	0.0295 (18)	0.0204 (17)	0.043 (2)	−0.0020 (14)	0.0062 (16)	−0.0070 (15)
C10	0.0277 (18)	0.0213 (17)	0.039 (2)	−0.0002 (14)	0.0004 (16)	0.0029 (15)
C11	0.0215 (16)	0.0225 (16)	0.031 (2)	−0.0009 (13)	0.0028 (14)	0.0022 (14)
C12	0.0319 (19)	0.0284 (18)	0.031 (2)	−0.0025 (15)	−0.0036 (15)	0.0093 (15)
C13	0.0331 (19)	0.0324 (19)	0.0234 (19)	−0.0022 (15)	−0.0050 (15)	0.0068 (15)
C14	0.0264 (17)	0.0267 (17)	0.0257 (19)	−0.0027 (14)	−0.0019 (14)	−0.0011 (14)
C15	0.0182 (15)	0.0235 (16)	0.0219 (18)	0.0003 (12)	0.0019 (13)	0.0000 (13)
C16	0.0163 (15)	0.0221 (16)	0.0270 (19)	0.0000 (12)	0.0022 (13)	−0.0031 (13)
C21	0.0224 (16)	0.0277 (18)	0.0185 (17)	0.0008 (13)	0.0010 (13)	−0.0069 (14)
C22	0.0237 (16)	0.0266 (17)	0.0234 (18)	0.0055 (13)	0.0000 (13)	0.0016 (14)
C23	0.0175 (15)	0.0279 (17)	0.0262 (19)	−0.0020 (13)	0.0020 (13)	0.0030 (14)
C24	0.0219 (16)	0.0253 (17)	0.0206 (18)	−0.0006 (13)	−0.0001 (13)	−0.0052 (13)
C25	0.0280 (18)	0.0344 (19)	0.029 (2)	0.0006 (15)	0.0007 (15)	−0.0017 (15)
C26	0.035 (2)	0.043 (2)	0.034 (2)	0.0011 (17)	−0.0031 (16)	−0.0111 (17)
C27	0.0276 (19)	0.033 (2)	0.047 (3)	−0.0035 (15)	0.0021 (17)	−0.0173 (17)
C28	0.0197 (16)	0.0259 (18)	0.041 (2)	−0.0021 (13)	0.0039 (15)	−0.0067 (15)
C29	0.0251 (19)	0.0228 (18)	0.066 (3)	−0.0030 (14)	0.0116 (18)	−0.0061 (18)
C30	0.031 (2)	0.0227 (18)	0.058 (3)	0.0022 (15)	0.0074 (18)	0.0043 (17)
C31	0.0221 (17)	0.0229 (17)	0.045 (2)	0.0023 (13)	0.0080 (16)	0.0047 (15)
C32	0.0296 (19)	0.033 (2)	0.039 (2)	0.0071 (15)	0.0097 (16)	0.0145 (17)
C33	0.0324 (19)	0.036 (2)	0.028 (2)	0.0047 (15)	0.0043 (15)	0.0089 (16)
C34	0.0279 (18)	0.0299 (18)	0.028 (2)	0.0019 (14)	0.0038 (15)	−0.0006 (15)
C35	0.0183 (16)	0.0234 (16)	0.0289 (19)	0.0008 (12)	0.0060 (14)	0.0002 (14)
C36	0.0167 (15)	0.0241 (17)	0.033 (2)	−0.0017 (13)	0.0050 (14)	−0.0038 (14)

Geometric parameters (Å, º) top

Co1—O1	2.070 (2)	C3—H3B	0.97
Co1—O6	2.074 (2)	C5—C6	1.389 (4)
Co1—O4	2.084 (2)	C5—H5	0.93
Co1—N2	2.098 (2)	C6—C7	1.368 (4)
Co1—N1	2.116 (2)	C6—H6	0.93
Co1—O3	2.130 (2)	C7—C8	1.409 (5)
Co2—O12	2.060 (2)	C7—H7	0.93
Co2—O10	2.096 (2)	C8—C16	1.398 (4)
Co2—O7	2.117 (2)	C8—C9	1.433 (4)
Co2—N3	2.118 (2)	C9—C10	1.352 (5)
Co2—O9	2.118 (2)	C9—H9	0.93
Co2—N4	2.119 (2)	C10—C11	1.427 (4)
O1—C1	1.272 (4)	C10—H10	0.93
O2—C1	1.249 (3)	C11—C12	1.396 (4)
O3—C2	1.420 (3)	C11—C15	1.398 (4)
O3—C3	1.421 (3)	C12—C13	1.371 (4)
O4—C4	1.259 (3)	C12—H12	0.93
O5—C4	1.250 (3)	C13—C14	1.390 (4)
O6—H61	0.872	C13—H13	0.93
O6—H62	0.918	C14—H14	0.93
O7—C21	1.272 (3)	C15—C16	1.430 (4)
O8—C21	1.244 (3)	C21—C22	1.519 (4)
O9—C22	1.432 (3)	C22—H22A	0.97
O9—C23	1.433 (3)	C22—H22B	0.97
O10—C24	1.269 (3)	C23—C24	1.527 (4)
O11—C24	1.245 (3)	C23—H23A	0.97
O12—H121	0.911	C23—H23B	0.97
O12—H122	0.959	C25—C26	1.394 (4)
O21—H211	0.910	C25—H25	0.93
O21—H212	0.954	C26—C27	1.372 (5)
O22—H221	0.950	C26—H26	0.93
O22—H222	0.878	C27—C28	1.411 (5)
O23—H231	0.866	C27—H27	0.93
O23—H232	0.866	C28—C36	1.409 (4)
N1—C5	1.320 (4)	C28—C29	1.443 (5)
N1—C16	1.356 (4)	C29—C30	1.353 (5)
N2—C14	1.322 (4)	C29—H29	0.93
N2—C15	1.364 (4)	C30—C31	1.435 (5)
N3—C25	1.334 (4)	C30—H30	0.93
N3—C36	1.362 (4)	C31—C35	1.403 (4)
N4—C34	1.332 (4)	C31—C32	1.410 (5)
N4—C35	1.361 (4)	C32—C33	1.360 (5)
C1—C2	1.530 (4)	C32—H32	0.93
C2—H2A	0.97	C33—C34	1.398 (4)
C2—H2B	0.97	C33—H33	0.93
C3—C4	1.528 (4)	C34—H34	0.93
C3—H3A	0.97	C35—C36	1.447 (4)

O1—Co1—O6	91.84 (8)	C6—C7—C8	119.3 (3)
O1—Co1—O4	151.31 (9)	C6—C7—H7	120.4
O6—Co1—O4	92.54 (8)	C8—C7—H7	120.4
O1—Co1—N2	106.84 (9)	C16—C8—C7	116.9 (3)
O6—Co1—N2	93.29 (9)	C16—C8—C9	119.0 (3)
O4—Co1—N2	101.19 (9)	C7—C8—C9	124.1 (3)
O1—Co1—N1	93.18 (9)	C10—C9—C8	121.0 (3)
O6—Co1—N1	171.22 (9)	C10—C9—H9	119.5
O4—Co1—N1	86.49 (9)	C8—C9—H9	119.5
N2—Co1—N1	78.37 (10)	C9—C10—C11	121.0 (3)
O1—Co1—O3	76.25 (8)	C9—C10—H10	119.5
O6—Co1—O3	93.46 (8)	C11—C10—H10	119.5
O4—Co1—O3	75.19 (8)	C12—C11—C15	117.3 (3)
N2—Co1—O3	172.48 (9)	C12—C11—C10	123.6 (3)
N1—Co1—O3	94.73 (9)	C15—C11—C10	119.1 (3)
O12—Co2—O10	96.68 (8)	C13—C12—C11	119.5 (3)
O12—Co2—O7	88.71 (8)	C13—C12—H12	120.2
O10—Co2—O7	150.42 (8)	C11—C12—H12	120.2
O12—Co2—N3	165.06 (9)	C12—C13—C14	119.5 (3)
O10—Co2—N3	94.69 (9)	C12—C13—H13	120.2
O7—Co2—N3	86.17 (9)	C14—C13—H13	120.2
O12—Co2—O9	93.86 (8)	N2—C14—C13	122.7 (3)
O10—Co2—O9	75.25 (8)	N2—C14—H14	118.6
O7—Co2—O9	75.38 (8)	C13—C14—H14	118.6
N3—Co2—O9	98.41 (9)	N2—C15—C11	123.0 (3)
O12—Co2—N4	92.19 (9)	N2—C15—C16	116.9 (3)
O10—Co2—N4	89.41 (8)	C11—C15—C16	120.0 (3)
O7—Co2—N4	119.53 (9)	N1—C16—C8	123.2 (3)
N3—Co2—N4	78.24 (10)	N1—C16—C15	116.9 (3)
O9—Co2—N4	164.06 (8)	C8—C16—C15	119.8 (3)
C1—O1—Co1	118.15 (19)	O8—C21—O7	126.3 (3)
C2—O3—C3	117.6 (2)	O8—C21—C22	115.4 (3)
C2—O3—Co1	115.00 (17)	O7—C21—C22	118.2 (3)
C3—O3—Co1	114.33 (16)	O9—C22—C21	108.0 (2)
C4—O4—Co1	118.63 (18)	O9—C22—H22A	110.1
Co1—O6—H61	118.58	C21—C22—H22A	110.1
Co1—O6—H62	118.89	O9—C22—H22B	110.1
H61—O6—H62	96.88	C21—C22—H22B	110.1
C21—O7—Co2	118.13 (18)	H22A—C22—H22B	108.4
C22—O9—C23	116.0 (2)	O9—C23—C24	107.2 (2)
C22—O9—Co2	116.21 (16)	O9—C23—H23A	110.3
C23—O9—Co2	113.65 (17)	C24—C23—H23A	110.3
C24—O10—Co2	117.24 (18)	O9—C23—H23B	110.3
Co2—O12—H121	121.19	C24—C23—H23B	110.3
Co2—O12—H122	115.88	H23A—C23—H23B	108.5
H121—O12—H122	102.84	O11—C24—O10	125.3 (3)
H211—O21—H212	109.0	O11—C24—C23	116.9 (3)
H221—O22—H222	96.4	O10—C24—C23	117.8 (3)
H231—O23—H232	104.9	N3—C25—C26	123.0 (3)
C5—N1—C16	118.1 (3)	N3—C25—H25	118.5
C5—N1—Co1	128.1 (2)	C26—C25—H25	118.5
C16—N1—Co1	113.4 (2)	C27—C26—C25	119.3 (3)
C14—N2—C15	117.9 (3)	C27—C26—H26	120.3
C14—N2—Co1	128.1 (2)	C25—C26—H26	120.3
C15—N2—Co1	113.8 (2)	C26—C27—C28	119.6 (3)
C25—N3—C36	118.1 (3)	C26—C27—H27	120.2
C25—N3—Co2	128.1 (2)	C28—C27—H27	120.2
C36—N3—Co2	113.8 (2)	C36—C28—C27	117.3 (3)
C34—N4—C35	117.1 (3)	C36—C28—C29	118.0 (3)
C34—N4—Co2	128.3 (2)	C27—C28—C29	124.7 (3)
C35—N4—Co2	114.2 (2)	C30—C29—C28	121.6 (3)
O2—C1—O1	126.8 (3)	C30—C29—H29	119.2
O2—C1—C2	114.8 (3)	C28—C29—H29	119.2
O1—C1—C2	118.4 (3)	C29—C30—C31	121.6 (3)
O3—C2—C1	108.0 (2)	C29—C30—H30	119.2
O3—C2—H2A	110.1	C31—C30—H30	119.2
C1—C2—H2A	110.1	C35—C31—C32	117.2 (3)
O3—C2—H2B	110.1	C35—C31—C30	118.4 (3)
C1—C2—H2B	110.1	C32—C31—C30	124.4 (3)
H2A—C2—H2B	108.4	C33—C32—C31	119.6 (3)
O3—C3—C4	107.5 (2)	C33—C32—H32	120.2
O3—C3—H3A	110.2	C31—C32—H32	120.2
C4—C3—H3A	110.2	C32—C33—C34	119.2 (3)
O3—C3—H3B	110.2	C32—C33—H33	120.4
C4—C3—H3B	110.2	C34—C33—H33	120.4
H3A—C3—H3B	108.5	N4—C34—C33	123.5 (3)
O5—C4—O4	125.2 (3)	N4—C34—H34	118.2
O5—C4—C3	117.1 (3)	C33—C34—H34	118.2
O4—C4—C3	117.7 (3)	N4—C35—C31	123.4 (3)
N1—C5—C6	122.8 (3)	N4—C35—C36	116.3 (3)
N1—C5—H5	118.6	C31—C35—C36	120.3 (3)
C6—C5—H5	118.6	N3—C36—C28	122.7 (3)
C7—C6—C5	119.6 (3)	N3—C36—C35	117.2 (3)
C7—C6—H6	120.2	C28—C36—C35	120.1 (3)
C5—C6—H6	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O8	0.87	1.79	2.647 (3)	169
O6—H62···O11ⁱ	0.92	1.77	2.685 (3)	178
O12—H121···O5	0.91	1.77	2.676 (3)	175
O12—H122···O2ⁱⁱ	0.96	1.64	2.596 (3)	171
O21—H211···O1	0.91	2.04	2.933 (3)	166
O21—H212···O5ⁱ	0.95	1.95	2.890 (3)	168
O22—H221···O7	0.95	1.94	2.867 (3)	163
O22—H222···O11ⁱ	0.88	1.95	2.811 (3)	168
O23—H231···O10	0.87	2.07	2.915 (3)	165
O23—H232···O22ⁱⁱ	0.87	2.24	3.094 (3)	168

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

Experimental details

Crystal data
Chemical formula	[Co(C₄H₄O₅)(C₁₂H₈N₂)(H₂O)]·1.5H₂O
M_r	416.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.4722 (16), 24.3161 (9), 13.6729 (14)
β (°)	93.627 (1)
V (Å³)	3474.7 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.32 × 0.28 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Bruker, 1999)
T_min, T_max	0.715, 0.810
No. of measured, independent and observed [I > 2σ(I)] reflections	21949, 7932, 4856
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 0.93
No. of reflections	7932
No. of parameters	479
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.41

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Co1—O1	2.070 (2)	Co2—O12	2.060 (2)
Co1—O6	2.074 (2)	Co2—O10	2.096 (2)
Co1—O4	2.084 (2)	Co2—O7	2.117 (2)
Co1—N2	2.098 (2)	Co2—N3	2.118 (2)
Co1—N1	2.116 (2)	Co2—O9	2.118 (2)
Co1—O3	2.130 (2)	Co2—N4	2.119 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H61···O8	0.87	1.79	2.647 (3)	169
O6—H62···O11ⁱ	0.92	1.77	2.685 (3)	178
O12—H121···O5	0.91	1.77	2.676 (3)	175
O12—H122···O2ⁱⁱ	0.96	1.64	2.596 (3)	171
O21—H211···O1	0.91	2.04	2.933 (3)	166
O21—H212···O5ⁱ	0.95	1.95	2.890 (3)	168
O22—H221···O7	0.95	1.94	2.867 (3)	163
O22—H222···O11ⁱ	0.88	1.95	2.811 (3)	168
O23—H231···O10	0.87	2.07	2.915 (3)	165
O23—H232···O22ⁱⁱ	0.87	2.24	3.094 (3)	168

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

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