Bis[6-(1H-benzimidazol-2-yl-κN)pyridine-2-carboxyl-ato-κN,O]cobalt(II) dihydrate.

In the title compound, [Co(C(13)H(8)N(3)O(2))(2)]·2H(2)O, the Co(II) atom has a distorted octa-hedral environment defined by four N atoms and two O atoms from two 6-(1H-benzimidazol-2-yl)pyridine-2-carboxyl-ate ligands. In the crystal, the complex mol-ecules and uncoordinated water mol-ecules are linked via N-H⋯O and O-H⋯O hydrogen bonds, forming a two-dimensional supra-molecular structure parallel to (010). π-π inter-actions 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].

Related literature

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

Crystal data

[Co(C13H8N3O2)2]·2H2O

M = 571.41

Monoclinic,

a = 9.8602 (5) Å

b = 20.3681 (11) Å

c = 13.1069 (7) Å

β = 111.453 (1)°

V = 2449.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 185 K

0.24 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.839, T max = 0.915

13443 measured reflections

4827 independent reflections

3864 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.150

S = 1.06

4827 reflections

352 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.59 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053700/hy2495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053700/hy2495Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(C13H8N3O2)2]·2H2O	F(000) = 1172
Mr = 571.41	Dx = 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

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

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(Fo2) + (0.0767P)2 + 2.8721P] where P = (Fo2 + 2Fc2)/3
4827 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.96 e Å−3
6 restraints	Δρmin = −0.59 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) .