Bis[6-(1H-benzimidazol-2-yl-κN3)pyridine-2-carboxyl­ato-κ2N,O]cobalt(II) dihydrate

Han, L.; Sun, D.

doi:10.1107/S1600536811053700

Bis[6-(1H-benzimidazol-2-yl-κN³)pyridine-2-carboxylato-κ²N,O]cobalt(II) dihydrate

In the title compound, [Co(C₁₃H₈N₃O₂)₂]·2H₂O, the Co^II atom has a distorted octahedral environment defined by four N atoms and two O atoms from two 6-(1H-benzimidazol-2-yl)pyridine-2-carboxylate ligands. In the crystal, the complex molecules and uncoordinated water molecules are linked via N—H

O and O—H

O hydrogen bonds, forming a two-dimensional supramolecular structure parallel to (010). π–π interactions are present between the imidazole, pyridine and benzene rings [centroid–centroid distances = 3.528 (2), 3.592 (2), 3.680 (2) and 3.732 (3) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811053700/hy2495sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811053700/hy2495Isup2.hkl Contains datablock I

CCDC reference: 861710

checkCIF report

Key indicators

Single-crystal X-ray study
T = 185 K
Mean (C-C) = 0.006 Å
R factor = 0.049
wR factor = 0.150
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        3.2 Ratio
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          4

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Molecular self-assembly of supramolecular architectures has received much attention during recent decades (Chun et al., 2005; Tranchemontagne et al., 2009). The structures and properties of such systems depend on the coordination and geometric preferences of both the central metal ions and bridging building blocks, as well as on the influence of weaker non-covalent interactions, such as hydrogen bonds and π–π stacking interactions. Multidentate ligands containing rich coordination sites (N and/or O donors) are often employed to produce polymeric networks with structural diversity owing to their various coordination modes (Eubank et al., 2011; Wang et al., 2009). Recently, we obtained the title mononuclear complex by the reaction of cobalt chloride with 6-(1H-benzimidazol-2-yl)pyridine-2-carboxylic acid using hydrothermal methods and its crystal structure is reported here.

In the title compound, the Co^II atom has a distorted octahedral environment with four N atoms and two carboxylate O atoms from two 6-(1H-benzimidazol-2-yl)pyridine-2-carboxylate ligands (Fig. 1). The bond lengths and angles around the Co atom are normal. The complex molecules and uncoordinated water molecules are connected into a two-dimensional structure by extensive N—H···O and O—H···O hydrogen bonds (Fig. 2, Table 1). π–π interactions between the imidazole, pyridine and benzene rings are present [centroid–centroid distances = 3.528 (2), 3.592 (2), 3.680 (2) and 3.732 (3) Å].

Related literature top

For background to supramolecular architectures, see: Chun et al. (2005); Tranchemontagne et al. (2009). For related complexes with multidentate ligands, see: Eubank et al. (2011); Wang et al. (2009).

Experimental top

The synthesis was performed under hydrothermal conditions. A mixture of CoCl₂.6H₂O (0.2 mmol, 0.050 g), 6-(1H-benzimidazol-2-yl)pyridine-2-carboxylic acid (0.4 mmol, 0.098 g), NaOH (0.4 mmol, 0.016 g) and H₂O (15 ml) in a 25 ml stainless steel reactor with a Teflon liner was heated from 293 to 433 K in 2 h and a constant temperature was maintained at 433 K for 72 h. After the mixture was cooled to 298 K, pink crystals of the title compound were recovered from the reaction.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the two-dimensional structure of the title compound built by hydrogen bonds (dashed lines).

Bis[6-(1H-benzimidazol-2-yl-κN³)pyridine-2-carboxylato- κ²N,O]cobalt(II) dihydrate top

Crystal data top

[Co(C₁₃H₈N₃O₂)₂]·2H₂O	F(000) = 1172
M_r = 571.41	D_x = 1.549 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4827 reflections
a = 9.8602 (5) Å	θ = 1.0–26.0°
b = 20.3681 (11) Å	µ = 0.76 mm⁻¹
c = 13.1069 (7) Å	T = 185 K
β = 111.453 (1)°	Block, pink
V = 2449.9 (2) Å³	0.24 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4827 independent reflections
Radiation source: fine-focus sealed tube	3864 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→10
T_min = 0.839, T_max = 0.915	k = −23→25
13443 measured reflections	l = −16→16

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0767P)² + 2.8721P] where P = (F_o² + 2F_c²)/3
4827 reflections	(Δ/σ)_max = 0.001
352 parameters	Δρ_max = 0.96 e Å⁻³
6 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Co(C₁₃H₈N₃O₂)₂]·2H₂O	V = 2449.9 (2) Å³
M_r = 571.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8602 (5) Å	µ = 0.76 mm⁻¹
b = 20.3681 (11) Å	T = 185 K
c = 13.1069 (7) Å	0.24 × 0.15 × 0.12 mm
β = 111.453 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4827 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3864 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.915	R_int = 0.026
13443 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	6 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.06	Δρ_max = 0.96 e Å⁻³
4827 reflections	Δρ_min = −0.59 e Å⁻³
352 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.1555 (4)	0.35179 (16)	0.7579 (3)	0.0386 (8)
C2	0.3187 (4)	0.35664 (15)	0.8211 (3)	0.0321 (7)
C3	0.4130 (4)	0.30476 (16)	0.8634 (3)	0.0384 (8)
H3A	0.3779	0.2609	0.8558	0.046*
C4	0.5581 (4)	0.31795 (16)	0.9164 (3)	0.0404 (8)
H4A	0.6245	0.2829	0.9462	0.048*
C5	0.6094 (4)	0.38247 (16)	0.9270 (3)	0.0356 (7)
H5A	0.7100	0.3920	0.9631	0.043*
C6	0.5091 (3)	0.43192 (15)	0.8833 (2)	0.0290 (6)
C7	0.5339 (3)	0.50287 (14)	0.8836 (2)	0.0278 (6)
C8	0.6304 (3)	0.60145 (15)	0.9040 (3)	0.0308 (7)
C9	0.7184 (4)	0.65706 (16)	0.9248 (3)	0.0393 (8)
H9A	0.8210	0.6545	0.9619	0.047*
C10	0.6487 (4)	0.71598 (17)	0.8885 (3)	0.0420 (8)
H10A	0.7052	0.7550	0.9002	0.050*
C11	0.4972 (4)	0.72036 (16)	0.8348 (3)	0.0388 (8)
H11A	0.4534	0.7621	0.8127	0.047*
C12	0.4113 (4)	0.66545 (15)	0.8138 (3)	0.0337 (7)
H12A	0.3087	0.6684	0.7771	0.040*
C13	0.4794 (3)	0.60507 (14)	0.8482 (3)	0.0287 (6)
C14	0.0579 (4)	0.57477 (19)	0.8491 (4)	0.0512 (10)
C15	0.0334 (4)	0.60199 (19)	0.7370 (3)	0.0502 (10)
C16	−0.0381 (5)	0.6601 (2)	0.6968 (4)	0.0728 (16)
H16A	−0.0828	0.6848	0.7375	0.087*
C17	−0.0424 (6)	0.6812 (2)	0.5950 (4)	0.088 (2)
H17A	−0.0897	0.7214	0.5657	0.105*
C18	0.0215 (6)	0.6445 (2)	0.5353 (4)	0.0763 (16)
H18A	0.0188	0.6586	0.4655	0.092*
C19	0.0896 (4)	0.58621 (18)	0.5817 (3)	0.0498 (10)
C20	0.1695 (4)	0.54082 (17)	0.5376 (3)	0.0446 (9)
C21	0.2695 (5)	0.49105 (19)	0.4359 (3)	0.0518 (10)
C22	0.3211 (6)	0.4676 (3)	0.3561 (4)	0.0721 (14)
H22A	0.2964	0.4887	0.2870	0.087*
C23	0.4077 (6)	0.4137 (3)	0.3816 (4)	0.0718 (14)
H23A	0.4428	0.3967	0.3283	0.086*
C24	0.4476 (5)	0.3820 (2)	0.4829 (4)	0.0620 (11)
H24A	0.5105	0.3450	0.4976	0.074*
C25	0.3962 (4)	0.40391 (19)	0.5622 (3)	0.0486 (9)
H25A	0.4216	0.3824	0.6310	0.058*
C26	0.3061 (4)	0.45864 (17)	0.5370 (3)	0.0409 (8)
N1	0.3673 (3)	0.41784 (12)	0.8317 (2)	0.0284 (5)
N2	0.4214 (3)	0.54241 (12)	0.8366 (2)	0.0287 (6)
N3	0.6612 (3)	0.53553 (13)	0.9257 (2)	0.0334 (6)
H3	0.7476	0.5182	0.9605	0.040*
N4	0.0940 (3)	0.56671 (14)	0.6808 (3)	0.0421 (7)
N5	0.2413 (3)	0.49147 (13)	0.5994 (2)	0.0363 (6)
N6	0.1837 (4)	0.54260 (16)	0.4400 (3)	0.0599 (10)
H6	0.1447	0.5718	0.3879	0.072*
O1	0.0911 (2)	0.40631 (11)	0.7254 (2)	0.0416 (6)
O2	0.0977 (3)	0.29740 (13)	0.7412 (3)	0.0601 (8)
O1W	0.1067 (4)	0.5642 (2)	1.1243 (4)	0.1120 (16)
H1A	0.0385	0.5579	1.1501	0.168*
H1B	0.0679	0.5744	1.0559	0.168*
O2W	−0.2043 (5)	0.3346 (3)	0.7130 (6)	0.179 (3)
H2A	−0.1389	0.3089	0.7008	0.268*
H2B	−0.1663	0.3533	0.7805	0.268*
O3	0.1308 (3)	0.52097 (12)	0.8735 (2)	0.0477 (6)
O4	0.0139 (3)	0.60542 (18)	0.9118 (3)	0.0748 (10)
Co1	0.22295 (4)	0.49008 (2)	0.75644 (4)	0.03024 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0422 (19)	0.0317 (18)	0.0419 (19)	−0.0054 (15)	0.0154 (16)	0.0014 (14)
C2	0.0403 (18)	0.0260 (16)	0.0333 (16)	−0.0007 (13)	0.0174 (14)	0.0001 (12)
C3	0.051 (2)	0.0225 (16)	0.0437 (19)	0.0005 (14)	0.0198 (16)	0.0011 (13)
C4	0.048 (2)	0.0294 (17)	0.0440 (19)	0.0130 (15)	0.0165 (16)	0.0032 (14)
C5	0.0355 (17)	0.0300 (17)	0.0404 (18)	0.0058 (13)	0.0128 (14)	−0.0023 (14)
C6	0.0319 (16)	0.0270 (16)	0.0303 (16)	0.0031 (12)	0.0140 (13)	−0.0006 (12)
C7	0.0294 (16)	0.0278 (15)	0.0289 (16)	0.0022 (12)	0.0140 (13)	−0.0021 (12)
C8	0.0311 (16)	0.0282 (16)	0.0358 (17)	0.0018 (12)	0.0155 (13)	−0.0029 (13)
C9	0.0330 (17)	0.0362 (18)	0.050 (2)	−0.0053 (14)	0.0168 (16)	−0.0043 (15)
C10	0.044 (2)	0.0309 (18)	0.054 (2)	−0.0087 (15)	0.0213 (17)	−0.0022 (15)
C11	0.0444 (19)	0.0281 (17)	0.045 (2)	0.0003 (14)	0.0172 (16)	0.0027 (14)
C12	0.0337 (17)	0.0282 (16)	0.0384 (18)	0.0024 (13)	0.0122 (14)	0.0026 (13)
C13	0.0317 (16)	0.0262 (15)	0.0330 (16)	−0.0021 (12)	0.0176 (13)	−0.0032 (12)
C14	0.0300 (18)	0.049 (2)	0.073 (3)	0.0037 (16)	0.0162 (18)	−0.020 (2)
C15	0.0327 (19)	0.046 (2)	0.056 (2)	0.0075 (16)	−0.0028 (16)	−0.0218 (18)
C16	0.058 (3)	0.059 (3)	0.068 (3)	0.031 (2)	−0.016 (2)	−0.027 (2)
C17	0.095 (4)	0.052 (3)	0.068 (3)	0.041 (3)	−0.027 (3)	−0.019 (2)
C18	0.098 (4)	0.042 (2)	0.049 (2)	0.020 (2)	−0.020 (2)	−0.0059 (19)
C19	0.054 (2)	0.0320 (18)	0.043 (2)	0.0024 (16)	−0.0060 (17)	−0.0085 (15)
C20	0.054 (2)	0.0291 (18)	0.0378 (19)	−0.0060 (16)	0.0019 (16)	−0.0007 (14)
C21	0.069 (3)	0.045 (2)	0.042 (2)	−0.0137 (19)	0.020 (2)	−0.0004 (17)
C22	0.110 (4)	0.069 (3)	0.049 (3)	−0.016 (3)	0.044 (3)	−0.001 (2)
C23	0.093 (4)	0.080 (3)	0.063 (3)	−0.011 (3)	0.054 (3)	−0.008 (3)
C24	0.070 (3)	0.058 (3)	0.072 (3)	−0.001 (2)	0.042 (2)	−0.013 (2)
C25	0.058 (2)	0.047 (2)	0.051 (2)	0.0019 (18)	0.0310 (19)	−0.0018 (17)
C26	0.048 (2)	0.0347 (18)	0.044 (2)	−0.0115 (15)	0.0210 (16)	−0.0069 (15)
N1	0.0339 (14)	0.0228 (12)	0.0306 (13)	0.0019 (10)	0.0143 (11)	0.0002 (10)
N2	0.0276 (13)	0.0253 (13)	0.0342 (14)	0.0013 (10)	0.0124 (11)	−0.0012 (10)
N3	0.0255 (13)	0.0306 (14)	0.0428 (16)	0.0031 (11)	0.0109 (12)	−0.0021 (12)
N4	0.0343 (15)	0.0312 (15)	0.0485 (18)	0.0017 (12)	0.0004 (13)	−0.0095 (13)
N5	0.0421 (16)	0.0287 (14)	0.0378 (16)	−0.0047 (12)	0.0141 (13)	−0.0024 (11)
N6	0.093 (3)	0.0400 (19)	0.0360 (18)	−0.0024 (18)	0.0105 (18)	0.0061 (14)
O1	0.0357 (13)	0.0314 (12)	0.0534 (15)	−0.0017 (10)	0.0111 (11)	0.0030 (11)
O2	0.0529 (17)	0.0332 (14)	0.082 (2)	−0.0138 (12)	0.0099 (15)	0.0031 (13)
O1W	0.063 (2)	0.130 (3)	0.157 (4)	0.002 (2)	0.056 (2)	0.065 (3)
O2W	0.064 (3)	0.174 (6)	0.278 (8)	−0.023 (3)	0.038 (4)	−0.033 (5)
O3	0.0461 (15)	0.0418 (14)	0.0653 (17)	−0.0004 (11)	0.0321 (13)	−0.0061 (12)
O4	0.0603 (19)	0.086 (2)	0.082 (2)	0.0234 (17)	0.0312 (17)	−0.0224 (18)
Co1	0.0299 (3)	0.0230 (2)	0.0377 (3)	0.00136 (16)	0.01228 (19)	−0.00077 (17)

Geometric parameters (Å, º) top

C1—O2	1.228 (4)	C16—H16A	0.9500
C1—O1	1.273 (4)	C17—C18	1.389 (8)
C1—C2	1.520 (5)	C17—H17A	0.9500
C2—N1	1.324 (4)	C18—C19	1.390 (5)
C2—C3	1.383 (5)	C18—H18A	0.9500
C3—C4	1.369 (5)	C19—N4	1.344 (5)
C3—H3A	0.9500	C19—C20	1.463 (6)
C4—C5	1.396 (5)	C20—N5	1.322 (4)
C4—H4A	0.9500	C20—N6	1.337 (5)
C5—C6	1.381 (4)	C21—N6	1.362 (6)
C5—H5A	0.9500	C21—C22	1.403 (6)
C6—N1	1.343 (4)	C21—C26	1.404 (5)
C6—C7	1.466 (4)	C22—C23	1.356 (7)
C7—N2	1.326 (4)	C22—H22A	0.9500
C7—N3	1.347 (4)	C23—C24	1.398 (7)
C8—N3	1.383 (4)	C23—H23A	0.9500
C8—C9	1.392 (4)	C24—C25	1.386 (5)
C8—C13	1.400 (4)	C24—H24A	0.9500
C9—C10	1.379 (5)	C25—C26	1.388 (5)
C9—H9A	0.9500	C25—H25A	0.9500
C10—C11	1.402 (5)	C26—N5	1.381 (4)
C10—H10A	0.9500	N1—Co1	2.034 (2)
C11—C12	1.369 (5)	N2—Co1	2.137 (3)
C11—H11A	0.9500	N3—H3	0.8800
C12—C13	1.395 (4)	N4—Co1	2.028 (3)
C12—H12A	0.9500	N5—Co1	2.132 (3)
C13—N2	1.384 (4)	N6—H6	0.8800
C14—O4	1.231 (5)	O1—Co1	2.093 (2)
C14—O3	1.285 (5)	O1W—H1A	0.8661
C14—C15	1.506 (6)	O1W—H1B	0.8622
C15—N4	1.318 (5)	O2W—H2A	0.8899
C15—C16	1.380 (5)	O2W—H2B	0.9083
C16—C17	1.388 (8)	O3—Co1	2.144 (3)

O2—C1—O1	125.8 (3)	N5—C20—C19	118.9 (3)
O2—C1—C2	119.0 (3)	N6—C20—C19	128.3 (3)
O1—C1—C2	115.1 (3)	N6—C21—C22	133.8 (4)
N1—C2—C3	120.9 (3)	N6—C21—C26	105.9 (3)
N1—C2—C1	112.9 (3)	C22—C21—C26	120.3 (4)
C3—C2—C1	126.3 (3)	C23—C22—C21	117.4 (4)
C4—C3—C2	118.6 (3)	C23—C22—H22A	121.3
C4—C3—H3A	120.7	C21—C22—H22A	121.3
C2—C3—H3A	120.7	C22—C23—C24	122.7 (4)
C3—C4—C5	120.5 (3)	C22—C23—H23A	118.6
C3—C4—H4A	119.7	C24—C23—H23A	118.6
C5—C4—H4A	119.7	C25—C24—C23	120.7 (4)
C6—C5—C4	117.8 (3)	C25—C24—H24A	119.6
C6—C5—H5A	121.1	C23—C24—H24A	119.6
C4—C5—H5A	121.1	C24—C25—C26	117.2 (4)
N1—C6—C5	120.6 (3)	C24—C25—H25A	121.4
N1—C6—C7	110.8 (3)	C26—C25—H25A	121.4
C5—C6—C7	128.6 (3)	N5—C26—C25	129.9 (3)
N2—C7—N3	112.7 (3)	N5—C26—C21	108.5 (3)
N2—C7—C6	119.1 (3)	C25—C26—C21	121.6 (4)
N3—C7—C6	128.2 (3)	C2—N1—C6	121.6 (3)
N3—C8—C9	132.5 (3)	C2—N1—Co1	117.9 (2)
N3—C8—C13	105.7 (3)	C6—N1—Co1	120.3 (2)
C9—C8—C13	121.8 (3)	C7—N2—C13	105.5 (3)
C10—C9—C8	116.4 (3)	C7—N2—Co1	112.7 (2)
C10—C9—H9A	121.8	C13—N2—Co1	141.4 (2)
C8—C9—H9A	121.8	C7—N3—C8	107.1 (3)
C9—C10—C11	122.3 (3)	C7—N3—H3	126.5
C9—C10—H10A	118.9	C8—N3—H3	126.5
C11—C10—H10A	118.9	C15—N4—C19	121.2 (3)
C12—C11—C10	121.1 (3)	C15—N4—Co1	118.5 (3)
C12—C11—H11A	119.5	C19—N4—Co1	119.5 (2)
C10—C11—H11A	119.5	C20—N5—C26	105.4 (3)
C11—C12—C13	117.8 (3)	C20—N5—Co1	112.7 (2)
C11—C12—H12A	121.1	C26—N5—Co1	141.9 (2)
C13—C12—H12A	121.1	C20—N6—C21	107.5 (3)
N2—C13—C12	130.3 (3)	C20—N6—H6	126.2
N2—C13—C8	109.1 (3)	C21—N6—H6	126.2
C12—C13—C8	120.6 (3)	C1—O1—Co1	116.6 (2)
O4—C14—O3	124.6 (4)	H1A—O1W—H1B	109.2
O4—C14—C15	119.7 (4)	H2A—O2W—H2B	110.8
O3—C14—C15	115.6 (3)	C14—O3—Co1	114.7 (3)
N4—C15—C16	121.9 (4)	N4—Co1—N1	174.98 (11)
N4—C15—C14	113.6 (3)	N4—Co1—O1	107.37 (10)
C16—C15—C14	124.4 (4)	N1—Co1—O1	77.25 (10)
C15—C16—C17	117.6 (4)	N4—Co1—N5	77.12 (12)
C15—C16—H16A	121.2	N1—Co1—N5	100.74 (10)
C17—C16—H16A	121.2	O1—Co1—N5	95.12 (10)
C16—C17—C18	121.0 (4)	N4—Co1—N2	98.86 (10)
C16—C17—H17A	119.5	N1—Co1—N2	76.70 (10)
C18—C17—H17A	119.5	O1—Co1—N2	153.43 (10)
C17—C18—C19	117.4 (5)	N5—Co1—N2	94.71 (10)
C17—C18—H18A	121.3	N4—Co1—O3	76.70 (12)
C19—C18—H18A	121.3	N1—Co1—O3	105.66 (10)
N4—C19—C18	121.0 (4)	O1—Co1—O3	89.01 (10)
N4—C19—C20	111.3 (3)	N5—Co1—O3	153.54 (11)
C18—C19—C20	127.6 (4)	N2—Co1—O3	93.05 (10)
N5—C20—N6	112.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱ	0.88	2.21	2.917 (4)	137
N6—H6···O1ⁱⁱ	0.88	2.30	2.971 (4)	133
O1W—H1A···O3ⁱⁱⁱ	0.87	2.26	2.923 (4)	134
O1W—H1B···O4	0.86	1.87	2.727 (6)	170
O2W—H2A···O2	0.89	2.21	2.962 (6)	142
O2W—H2B···O1Wⁱⁱⁱ	0.91	2.05	2.867 (8)	149

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₃H₈N₃O₂)₂]·2H₂O
M_r	571.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	185
a, b, c (Å)	9.8602 (5), 20.3681 (11), 13.1069 (7)
β (°)	111.453 (1)
V (Å³)	2449.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.24 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.839, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	13443, 4827, 3864
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.150, 1.06
No. of reflections	4827
No. of parameters	352
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.59

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).