Aqua­(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)(formato-κ2O,O′)(formato-κO)cobalt(II) monohydrate

Ni, S.-L.; Xia, P.; Cao, F.

doi:10.1107/S1600536810050051

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages m39-m40

https://doi.org/10.1107/S1600536810050051

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Aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(formato-κ²O,O′)(formato-κO)cobalt(II) monohydrate

Sheng-Liang Ni,^a ^* Ping Xia ^a and Feng Cao ^a

^aDepartment of Chemistry, Huzhou Teachers College, Huzhou Key Laboratory Base of Novel Functional Materials, Huzhou, Zhejiang 313000, People's Republic of China
^*Correspondence e-mail: shengliangni@163.com

(Received 24 November 2010; accepted 30 November 2010; online 4 December 2010)

The asymmetric unit of the title compound, [Co(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O, contains a mononuclear complex molecule hydrogen bonded to a lattice water molecule. The Co^II cation is in a distorted octahedral coordination environment defined by the two N atoms of the 2,9-dimethyl-1,10-phenanthroline ligand and four O atoms. Two of these are from a chelating formate anion, one from a monodentate formate and the last from an aqua ligand. In the crystal, molecules are connected by O—H⋯O hydrogen bonds, forming double chains along [100] with the 2,9-dimethyl-1,10-phenanthroline ligands pointing outwards from each chain. These chains are further linked into layers parallel to (011) by inter-chain π–π stacking interactions with centroid–centroid distances of 3.61 (1) Å.

Related literature

For background to the formation and applications of supramolecular metal complexes, see: Moulton & Zaworotko (2001 ); Aakeroy & Seddon (1993 ). For related structures, see: Cai et al. (2008 ); Chen et al. (2009 ).

Experimental

Crystal data

[Co(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O
M_r = 393.25
Triclinic, $[P \overline 1]$
a = 7.4220 (15) Å
b = 10.441 (2) Å
c = 11.419 (2) Å
α = 82.92 (3)°
β = 81.62 (3)°
γ = 76.01 (3)°
V = 845.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 295 K
0.16 × 0.10 × 0.08 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (XSCANS; Siemens, 1996 ) T_min = 0.880, T_max = 0.912
4797 measured reflections
3897 independent reflections
3362 reflections with I > 2σ(I)
R_int = 0.017
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.03
3897 reflections
227 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected bond lengths (Å)

Co—O4	2.0552 (16)
Co—O1	2.0710 (17)
Co—N1	2.1194 (18)
Co—N2	2.1430 (16)
Co—O3	2.1622 (18)
Co—O2	2.2024 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O5ⁱ	0.85	1.84	2.688	173
O1—H1C⋯O6ⁱⁱ	0.84	1.98	2.774	156
O6—H6B⋯O3	0.85	1.96	2.809	176
O6—H6C⋯O4ⁱⁱⁱ	0.85	2.33	3.098	151
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1; (iii) -x, -y, -z+1.

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050051/sj5068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050051/sj5068Isup2.hkl

checkCIF report

Comment top

In the past decade, a variety of supramolecular architectures based on non–covalent intermolecular interactions such as hydrogen bonding, van der Walls forces and π–π interactions have been achieved by using transition metal centers and organic ligands due to their possible intriguing structural topologies and potential applications in optics, catalysis, ion exchange, gas storage, and the molecular–based magnetic materials (Aakeroy & Seddon, 1993). Carboxylate ligands have been actively utilized as construction units to obtain many supramolecular complexes (Moulton & Zaworotko, 2001) Herein, we are interested in self–assemblies of Co^II ions and 2,9-dimethyl-1,10-phenanthroline with formic acid, leading to the successful preparation of the complex [Co(H₂O)(C₁₄H₁₂N₂)(HCO₂)₂].H₂O.

The asymmetric unit of the title compound consists of one Co^II ion, a H₂O molecule, a 2,9-dimethyl-1,10-phenanthroline molecule, one O,O'–chelated formate anion and another coordinated formate anion, and one lattice H₂O molecule (Fig. 1). Each Co^II atom is coordinated two N atoms from one 2,9-dimethyl-1,10-phenanthroline, three O atoms from two formate anions and one aqua ligand to complete a distorted octahedral CoN₂O₄ chromophore. The Co–N/O distances of 2.055 (2)–2.143 (2) Å, Table 1, fall within the normal range (Cai et al., 2008, Chen et al., 2009), both the cisoid and transoid bond angles in the range 59.90 (8)–112.35 (7) Å and 167.31 (7)–176.05 (6) Å, respectively, indicating that the octahedral CoN₂O₄ geometry is a highly distorted one. For the two formate anions, the angle (O2–C15–O3, 122.6 (3)°) in the chelated formate is smaller than that in the anion that binds in a monodentate fashion (O4–C16–O5, 128.8 (2)°). The 2,9-dimethyl-1,10-phenanthroline ligand is almost coplanar with a mean square deviation 0.0163 Å. The O6 solvent water molecule is not coordinated to Co atom with the distance between the cobalt and water oxygen atoms of 4.800 (2) Å. However it is linked to the complex molecule in the asymmetric unit by an O6—H6B—O3 hydrogen bond.

The molecules are connected by (O1–H1B···O5^#1, O1–H1C···O6^#2 and O6–H6C···O4^#3) hydrogen bonds, Table 1, to form one-dimensional double chains along [100] with 2,9-dimethyl-1,10-phenanthroline orientating outwards. The resulting chains are further linked into two-dimensional layers parallel to (011) by interchain π–π stacking interactions with centroid – centroid distances 3.61 (1) Å), Fig. 2.

Related literature top

For background to the formation and applications of supramolecular metal complexes, see: Moulton & Zaworotko (2001); Aakeroy & Seddon (1993). For related structures, see: Cai et al. (2008); Chen et al. (2009).

Experimental top

Dropwise addition of 2.0 ml of 1.0 M aqueous Na₂CO₃ to a stirred aqueous solution of CoCl₂.6H₂O (0.2380 g, 1.0 mmol) in 5.0 ml H₂O produced a pink precipitate, Co(OH)_2–2x (CO₃)_x.yH₂O, which was centrifuged and washed with water until no Cl^- anions were detected in the supernatant. The precipitate was added to a stirred aqueous methanolic solution of 2,9-dimethyl-1,10-phenanthroline in 30 ml CH₃OH–H₂O (1/1 v/v). 1.77 ml of 1.0 M aqueous formic acid was added dropwise and stirred continuously until the pink precipitate dissolved. The pink solution (pH = 4.06) was allowed to stand at room temperature. Slow evaporation over several days afforded pink block shaped crystals. Yield:45% based on the initial CoCl₂.6H₂O input.

Structure description top

For background to the formation and applications of supramolecular metal complexes, see: Moulton & Zaworotko (2001); Aakeroy & Seddon (1993). For related structures, see: Cai et al. (2008); Chen et al. (2009).

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound. The displacement ellipsoids are drawn at 45% probability level.
	Fig. 2. The two-dimensional layer structure of the title compound linked through hydrogen bonds and π–π stacking interactions.

Aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N')(formato- κ²O,O')(formato-κO)cobalt(II) monohydrate top

Crystal data top

[Co(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O	Z = 2
M_r = 393.25	F(000) = 406
Triclinic, P1	D_x = 1.544 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4220 (15) Å	Cell parameters from 25 reflections
b = 10.441 (2) Å	θ = 5.0–12.5°
c = 11.419 (2) Å	µ = 1.05 mm⁻¹
α = 82.92 (3)°	T = 295 K
β = 81.62 (3)°	Block, pink
γ = 76.01 (3)°	0.16 × 0.10 × 0.08 mm
V = 845.9 (3) Å³

Data collection top

Bruker P4 diffractometer	3362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 27.5°, θ_min = 1.8°
θ/2θ scans	h = −1→9
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −13→13
T_min = 0.880, T_max = 0.912	l = −14→14
4797 measured reflections	3 standard reflections every 97 reflections
3897 independent reflections	intensity decay: none

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0543P)² + 0.2279P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3897 reflections	Δρ_max = 0.37 e Å⁻³
227 parameters	Δρ_min = −0.34 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.002468

Crystal data top

[Co(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O	γ = 76.01 (3)°
M_r = 393.25	V = 845.9 (3) Å³
Triclinic, P1	Z = 2
a = 7.4220 (15) Å	Mo Kα radiation
b = 10.441 (2) Å	µ = 1.05 mm⁻¹
c = 11.419 (2) Å	T = 295 K
α = 82.92 (3)°	0.16 × 0.10 × 0.08 mm
β = 81.62 (3)°

Data collection top

Bruker P4 diffractometer	3362 reflections with I > 2σ(I)
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	R_int = 0.017
T_min = 0.880, T_max = 0.912	3 standard reflections every 97 reflections
4797 measured reflections	intensity decay: none
3897 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	6 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.37 e Å⁻³
3897 reflections	Δρ_min = −0.34 e Å⁻³
227 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	0.27534 (4)	0.17941 (2)	0.27175 (2)	0.03146 (11)
N1	0.2555 (2)	0.25976 (17)	0.09313 (14)	0.0331 (3)
N2	0.2662 (2)	0.38360 (15)	0.28646 (14)	0.0305 (3)
O1	0.5639 (2)	0.15052 (15)	0.24594 (14)	0.0452 (4)
H1B	0.6115	0.2032	0.2767	0.068*
H1C	0.6274	0.0738	0.2635	0.068*
O2	0.3174 (3)	−0.03795 (17)	0.29174 (18)	0.0637 (5)
O3	0.2798 (3)	0.07298 (17)	0.44656 (15)	0.0551 (4)
O4	−0.0089 (2)	0.19581 (17)	0.29267 (15)	0.0474 (4)
O5	−0.2919 (2)	0.30672 (19)	0.35861 (16)	0.0539 (4)
O6	0.1515 (3)	0.06203 (18)	0.69063 (17)	0.0593 (5)
H6B	0.1849	0.0670	0.6158	0.089*
H6C	0.0747	0.0117	0.7018	0.089*
C1	0.2454 (3)	0.1974 (2)	−0.0004 (2)	0.0452 (5)
C2	0.2397 (4)	0.2645 (3)	−0.1146 (2)	0.0577 (7)
H2A	0.2335	0.2194	−0.1787	0.069*
C3	0.2432 (4)	0.3945 (3)	−0.1321 (2)	0.0576 (7)
H3A	0.2416	0.4381	−0.2081	0.069*
C4	0.2491 (3)	0.4633 (2)	−0.03500 (19)	0.0448 (5)
C5	0.2526 (4)	0.6003 (3)	−0.0464 (2)	0.0587 (7)
H5A	0.2480	0.6482	−0.1206	0.070*
C6	0.2625 (4)	0.6611 (2)	0.0489 (3)	0.0575 (7)
H6A	0.2655	0.7503	0.0395	0.069*
C7	0.2686 (3)	0.5909 (2)	0.1641 (2)	0.0436 (5)
C8	0.2817 (4)	0.6496 (2)	0.2655 (2)	0.0543 (6)
H8A	0.2870	0.7383	0.2597	0.065*
C9	0.2868 (4)	0.5763 (2)	0.3717 (2)	0.0504 (6)
H9A	0.2964	0.6150	0.4390	0.060*
C10	0.2776 (3)	0.4427 (2)	0.38166 (18)	0.0367 (4)
C11	0.2631 (3)	0.45609 (18)	0.17911 (18)	0.0320 (4)
C12	0.2558 (3)	0.39041 (19)	0.07673 (17)	0.0330 (4)
C13	0.2345 (5)	0.0557 (3)	0.0209 (3)	0.0657 (8)
H13A	0.2420	0.0262	0.1034	0.099*
H13B	0.3364	0.0031	−0.0266	0.099*
H13C	0.1181	0.0466	−0.0004	0.099*
C14	0.2786 (4)	0.3641 (3)	0.5002 (2)	0.0500 (6)
H14A	0.2716	0.2752	0.4914	0.075*
H14B	0.1729	0.4044	0.5531	0.075*
H14C	0.3918	0.3622	0.5324	0.075*
C15	0.3054 (5)	−0.0333 (3)	0.4003 (3)	0.0628 (7)
H15	0.3158	−0.1120	0.4494	0.075*
C16	−0.1206 (3)	0.2801 (2)	0.3492 (2)	0.0467 (5)
H16	−0.0681	0.3306	0.3905	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.03515 (17)	0.02810 (15)	0.03361 (16)	−0.01129 (10)	−0.00462 (10)	−0.00368 (10)
N1	0.0329 (8)	0.0380 (9)	0.0320 (8)	−0.0120 (7)	−0.0051 (6)	−0.0082 (6)
N2	0.0298 (8)	0.0298 (8)	0.0343 (8)	−0.0098 (6)	−0.0029 (6)	−0.0078 (6)
O1	0.0391 (8)	0.0407 (8)	0.0572 (10)	−0.0071 (6)	−0.0124 (7)	−0.0062 (7)
O2	0.0943 (15)	0.0355 (9)	0.0658 (12)	−0.0211 (9)	−0.0134 (11)	−0.0051 (8)
O3	0.0761 (12)	0.0468 (9)	0.0447 (9)	−0.0196 (9)	−0.0124 (8)	0.0042 (7)
O4	0.0358 (8)	0.0539 (9)	0.0561 (10)	−0.0159 (7)	−0.0003 (7)	−0.0135 (8)
O5	0.0345 (8)	0.0684 (11)	0.0627 (11)	−0.0125 (8)	−0.0044 (7)	−0.0209 (9)
O6	0.0680 (12)	0.0556 (10)	0.0575 (11)	−0.0154 (9)	−0.0121 (9)	−0.0099 (8)
C1	0.0466 (12)	0.0566 (14)	0.0382 (11)	−0.0176 (10)	−0.0055 (9)	−0.0143 (10)
C2	0.0650 (16)	0.0796 (19)	0.0350 (12)	−0.0207 (14)	−0.0096 (11)	−0.0173 (12)
C3	0.0606 (16)	0.0793 (19)	0.0319 (11)	−0.0174 (14)	−0.0071 (11)	0.0033 (11)
C4	0.0424 (12)	0.0518 (13)	0.0381 (11)	−0.0114 (10)	−0.0052 (9)	0.0064 (9)
C5	0.0621 (16)	0.0559 (15)	0.0535 (14)	−0.0178 (12)	−0.0079 (12)	0.0222 (12)
C6	0.0622 (16)	0.0355 (12)	0.0705 (17)	−0.0141 (11)	−0.0053 (13)	0.0146 (11)
C7	0.0420 (12)	0.0304 (10)	0.0580 (14)	−0.0110 (9)	−0.0009 (10)	−0.0030 (9)
C8	0.0588 (15)	0.0331 (11)	0.0744 (18)	−0.0166 (10)	0.0014 (13)	−0.0161 (11)
C9	0.0512 (13)	0.0456 (12)	0.0609 (15)	−0.0175 (10)	0.0029 (11)	−0.0282 (11)
C10	0.0333 (10)	0.0413 (11)	0.0392 (10)	−0.0118 (8)	−0.0012 (8)	−0.0153 (8)
C11	0.0279 (9)	0.0286 (9)	0.0398 (10)	−0.0072 (7)	−0.0037 (8)	−0.0028 (7)
C12	0.0291 (9)	0.0367 (10)	0.0332 (10)	−0.0089 (8)	−0.0042 (7)	−0.0003 (8)
C13	0.088 (2)	0.0612 (17)	0.0608 (16)	−0.0293 (15)	−0.0094 (15)	−0.0278 (13)
C14	0.0568 (14)	0.0630 (15)	0.0366 (11)	−0.0198 (12)	−0.0086 (10)	−0.0140 (10)
C15	0.086 (2)	0.0389 (13)	0.0647 (17)	−0.0232 (13)	−0.0157 (15)	0.0143 (12)
C16	0.0392 (12)	0.0604 (14)	0.0470 (12)	−0.0200 (11)	−0.0036 (10)	−0.0151 (11)

Geometric parameters (Å, º) top

Co—O4	2.0552 (16)	C3—H3A	0.9300
Co—O1	2.0710 (17)	C4—C12	1.404 (3)
Co—N1	2.1194 (18)	C4—C5	1.426 (4)
Co—N2	2.1430 (16)	C5—C6	1.345 (4)
Co—O3	2.1622 (18)	C5—H5A	0.9300
Co—O2	2.2024 (17)	C6—C7	1.426 (4)
Co—C15	2.488 (3)	C6—H6A	0.9300
N1—C1	1.337 (3)	C7—C8	1.401 (3)
N1—C12	1.354 (3)	C7—C11	1.406 (3)
N2—C10	1.337 (2)	C8—C9	1.353 (4)
N2—C11	1.359 (3)	C8—H8A	0.9300
O1—H1B	0.8536	C9—C10	1.403 (3)
O1—H1C	0.8425	C9—H9A	0.9300
O2—C15	1.236 (3)	C10—C14	1.494 (3)
O3—C15	1.249 (3)	C11—C12	1.440 (3)
O4—C16	1.229 (3)	C13—H13A	0.9600
O5—C16	1.225 (3)	C13—H13B	0.9600
O6—H6B	0.8529	C13—H13C	0.9600
O6—H6C	0.8512	C14—H14A	0.9600
C1—C2	1.404 (4)	C14—H14B	0.9600
C1—C13	1.489 (4)	C14—H14C	0.9600
C2—C3	1.353 (4)	C15—H15	0.9300
C2—H2A	0.9300	C16—H16	0.9300
C3—C4	1.405 (4)

O4—Co—O1	176.05 (6)	C6—C5—C4	120.8 (2)
O4—Co—N1	88.20 (7)	C6—C5—H5A	119.6
O1—Co—N1	91.40 (7)	C4—C5—H5A	119.6
O4—Co—N2	96.90 (7)	C5—C6—C7	121.1 (2)
O1—Co—N2	86.88 (7)	C5—C6—H6A	119.5
N1—Co—N2	79.03 (7)	C7—C6—H6A	119.5
O4—Co—O3	87.65 (8)	C8—C7—C11	117.2 (2)
O1—Co—O3	92.21 (8)	C8—C7—C6	123.0 (2)
N1—Co—O3	171.25 (6)	C11—C7—C6	119.8 (2)
N2—Co—O3	109.13 (7)	C9—C8—C7	119.5 (2)
O4—Co—O2	89.29 (8)	C9—C8—H8A	120.3
O1—Co—O2	87.23 (8)	C7—C8—H8A	120.3
N1—Co—O2	112.35 (7)	C8—C9—C10	120.8 (2)
N2—Co—O2	167.32 (7)	C8—C9—H9A	119.6
O3—Co—O2	59.90 (8)	C10—C9—H9A	119.6
O4—Co—C15	88.17 (9)	N2—C10—C9	121.1 (2)
O1—Co—C15	89.74 (9)	N2—C10—C14	118.73 (18)
N1—Co—C15	141.97 (9)	C9—C10—C14	120.1 (2)
N2—Co—C15	138.97 (9)	N2—C11—C7	122.92 (19)
O3—Co—C15	30.14 (9)	N2—C11—C12	117.94 (16)
O2—Co—C15	29.76 (8)	C7—C11—C12	119.14 (19)
C1—N1—C12	118.95 (18)	N1—C12—C4	122.82 (19)
C1—N1—Co	128.10 (15)	N1—C12—C11	117.96 (17)
C12—N1—Co	112.95 (13)	C4—C12—C11	119.22 (19)
C10—N2—C11	118.44 (17)	C1—C13—H13A	109.5
C10—N2—Co	129.34 (14)	C1—C13—H13B	109.5
C11—N2—Co	111.99 (12)	H13A—C13—H13B	109.5
Co—O1—H1B	117.2	C1—C13—H13C	109.5
Co—O1—H1C	117.6	H13A—C13—H13C	109.5
H1B—O1—H1C	105.8	H13B—C13—H13C	109.5
C15—O2—Co	88.00 (15)	C10—C14—H14A	109.5
C15—O3—Co	89.50 (16)	C10—C14—H14B	109.5
C16—O4—Co	123.21 (15)	H14A—C14—H14B	109.5
H6B—O6—H6C	104.7	C10—C14—H14C	109.5
N1—C1—C2	121.0 (2)	H14A—C14—H14C	109.5
N1—C1—C13	118.0 (2)	H14B—C14—H14C	109.5
C2—C1—C13	121.0 (2)	O2—C15—O3	122.6 (2)
C3—C2—C1	120.4 (2)	O2—C15—Co	62.23 (13)
C3—C2—H2A	119.8	O3—C15—Co	60.36 (13)
C1—C2—H2A	119.8	O2—C15—H15	118.7
C2—C3—C4	119.8 (2)	O3—C15—H15	118.7
C2—C3—H3A	120.1	Co—C15—H15	179.0
C4—C3—H3A	120.1	O5—C16—O4	128.8 (2)
C12—C4—C3	117.0 (2)	O5—C16—H16	115.6
C12—C4—C5	120.0 (2)	O4—C16—H16	115.6
C3—C4—C5	123.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O5ⁱ	0.85	1.84	2.688	173
O1—H1C···O6ⁱⁱ	0.84	1.98	2.774	156
O6—H6B···O3	0.85	1.96	2.809	176
O6—H6C···O4ⁱⁱⁱ	0.85	2.33	3.098	151

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

Experimental details

Crystal data
Chemical formula	[Co(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O
M_r	393.25
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.4220 (15), 10.441 (2), 11.419 (2)
α, β, γ (°)	82.92 (3), 81.62 (3), 76.01 (3)
V (Å³)	845.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.16 × 0.10 × 0.08

Data collection
Diffractometer	Bruker P4
Absorption correction	ψ scan (XSCANS; Siemens, 1996)
T_min, T_max	0.880, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	4797, 3897, 3362
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.03
No. of reflections	3897
No. of parameters	227
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.34

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006).

Selected bond lengths (Å) top

Co—O4	2.0552 (16)	Co—N2	2.1430 (16)
Co—O1	2.0710 (17)	Co—O3	2.1622 (18)
Co—N1	2.1194 (18)	Co—O2	2.2024 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O5ⁱ	0.854	1.838	2.688	173
O1—H1C···O6ⁱⁱ	0.843	1.980	2.774	156
O6—H6B···O3	0.853	1.957	2.809	176
O6—H6C···O4ⁱⁱⁱ	0.851	2.325	3.098	151

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

Acknowledgements

This project was supported by the Foundation of the Education Department of Zhejiang Province (ky23022) and the Huzhou Municipal Foundation of Science and Technology (2006YG21).

References

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