catena-Poly[[[diaqua-(1,10-phenanthroline-κ(2) N,N')cobalt(II)]-μ-1H-benzimidazole-5,6-dicarboxyl-ato-κ(2) N (3):O (6)] sesquihydrate}.

In the title compound, {[Co(C9H4N2O4)(C12H8N2)(H2O)2]·1.5H2O} n , the Co(II) atom is hexa-coordinated by one N atom and one O atom from two symmetry-related 1H-benzimidazole-5,6-dicarboxyl-ate ligands, two N atoms from one 1,10-phenanthroline ligand (phen) and two water mol-ecules. The dihedral angle between the 1H-benzimidazole-5,6-dicarboxyl-ate and 1,10-phenanthroline ligands is 74.41 (4)°. The crystal packing is governed by inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions. All water (coordin-ating and lattice) mol-ecules take part in the hydrogen-bonding inter-actions. In addition, there are π-π stacking inter-actions between inversion-related phen ligands, the shortest centroid-centroid distance being 3.7536 (16) Å. One of the two lattice water molecules shows half-occupancy.

Related literature

For general background to 1H-benzoimidazole-5,6-dicarboxyl­ate complexes, see: Lo et al. (2007 ▶); Gao et al. (2008 ▶); Yao et al. (2008 ▶). For 1,10-phenanthroline as a bridging ligand, see: Chesnut et al. (1999 ▶). For a similar structure with NiII, see: Song et al. (2009 ▶).

Experimental

Crystal data

[Co(C9H4N2O4)(C12H8N2)(H2O)2]·1.5H2O

M = 506.33

Monoclinic,

a = 9.7250 (11) Å

b = 11.3956 (13) Å

c = 19.296 (2) Å

β = 103.109 (2)°

V = 2082.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.88 mm−1

T = 173 K

0.30 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.776, T max = 0.838

17888 measured reflections

4797 independent reflections

3761 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.05

4796 reflections

331 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043760/zq2183sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043760/zq2183Isup2.hkl

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

[Co(C9H4N2O4)(C12H8N2)(H2O)2]·1.5H2O	F(000) = 1040
Mr = 506.33	Dx = 1.615 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4850 reflections
a = 9.7250 (11) Å	θ = 2.1–27.5°
b = 11.3956 (13) Å	µ = 0.88 mm−1
c = 19.296 (2) Å	T = 173 K
β = 103.109 (2)°	Prism, red
V = 2082.7 (4) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Rigaku Saturn724+ diffractometer	4797 independent reflections
Radiation source: fine-focus sealed tube	3761 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	h = −11→12
Tmin = 0.776, Tmax = 0.838	k = −14→14
17888 measured reflections	l = −25→25

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0355P)2 + 1.1164P] where P = (Fo2 + 2Fc2)/3
4796 reflections	(Δ/σ)max = 0.002
331 parameters	Δρmax = 0.42 e Å−3
12 restraints	Δρmin = −0.49 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	Occ. (<1)
C1	1.3426 (2)	0.48546 (18)	0.68601 (11)	0.0196 (4)
H1	1.4358	0.4878	0.6816	0.023*
C2	1.1479 (2)	0.42156 (18)	0.71347 (10)	0.0162 (4)
C3	1.1260 (2)	0.53227 (18)	0.68112 (10)	0.0158 (4)
C4	1.0404 (2)	0.36045 (18)	0.73494 (11)	0.0184 (4)
H4	1.0562	0.2867	0.7559	0.022*
C5	0.9938 (2)	0.58516 (18)	0.66973 (10)	0.0166 (4)
H5	0.9779	0.6581	0.6478	0.020*
C6	0.8856 (2)	0.52623 (18)	0.69192 (10)	0.0155 (4)
C7	0.9086 (2)	0.41394 (18)	0.72378 (10)	0.0162 (4)
C8	0.7474 (2)	0.59071 (19)	0.68525 (11)	0.0202 (4)
C9	0.7931 (2)	0.34525 (17)	0.74648 (11)	0.0173 (4)
C10	0.9568 (2)	0.1841 (2)	0.99354 (12)	0.0285 (5)
H10	0.9609	0.1120	0.9715	0.034*
C11	1.0612 (3)	0.2105 (3)	1.05439 (13)	0.0372 (6)
H11	1.1333	0.1573	1.0717	0.045*
C12	1.0563 (3)	0.3156 (3)	1.08825 (13)	0.0393 (7)
H12	1.1254	0.3346	1.1285	0.047*
C13	0.9455 (3)	0.3945 (2)	1.06151 (12)	0.0327 (6)
C14	0.8459 (2)	0.3620 (2)	0.99951 (11)	0.0243 (5)
C15	0.9306 (3)	0.5065 (3)	1.09338 (13)	0.0416 (7)
H15	0.9968	0.5290	1.1340	0.050*
C16	0.7329 (2)	0.4407 (2)	0.96903 (11)	0.0242 (5)
C17	0.8237 (3)	0.5794 (3)	1.06611 (14)	0.0420 (7)
H17	0.8160	0.6504	1.0887	0.050*
C18	0.7208 (3)	0.5495 (2)	1.00241 (13)	0.0310 (6)
C19	0.6081 (3)	0.6230 (2)	0.96966 (15)	0.0392 (6)
H19	0.5964	0.6958	0.9894	0.047*
C20	0.5165 (3)	0.5876 (2)	0.90918 (15)	0.0380 (6)
H20	0.4416	0.6354	0.8875	0.046*
C21	0.5363 (3)	0.4778 (2)	0.87982 (13)	0.0321 (6)
H21	0.4731	0.4545	0.8384	0.039*
N1	1.28761 (18)	0.39420 (15)	0.71539 (9)	0.0195 (4)
H1A	1.3311	0.3310	0.7321	0.023*
N2	1.25154 (17)	0.57083 (15)	0.66427 (9)	0.0172 (4)
N3	0.85195 (19)	0.25700 (17)	0.96580 (9)	0.0220 (4)
N4	0.64096 (19)	0.40575 (16)	0.90847 (9)	0.0237 (4)
O1	0.71519 (16)	0.66394 (16)	0.63497 (9)	0.0359 (4)
O2	0.67695 (16)	0.57174 (14)	0.73083 (8)	0.0279 (4)
O3	0.68891 (16)	0.31022 (14)	0.69976 (8)	0.0250 (4)
O4	0.81500 (15)	0.32296 (12)	0.81218 (7)	0.0191 (3)
OW1	0.51234 (15)	0.24220 (13)	0.77827 (8)	0.0184 (3)
H1C	0.5615	0.2496	0.7472	0.028*
H1D	0.4589	0.1824	0.7723	0.028*
OW2	0.55560 (16)	0.15584 (16)	0.92303 (8)	0.0280 (4)
H2C	0.4677	0.1657	0.9039	0.042*
H2D	0.5734	0.1556	0.9673	0.042*
OW3	0.5829 (3)	0.1182 (2)	1.06327 (10)	0.0635 (7)
H3C	0.6403	0.1383	1.1027	0.095*
H3D	0.5210	0.0701	1.0688	0.095*
OW4	1.2843 (5)	0.0672 (3)	1.0004 (2)	0.0451 (10)	0.50
H4C	1.3167	0.0004	0.9924	0.068*	0.50
H4D	1.2609	0.1116	0.9637	0.068*	0.50
Co1	0.69156 (3)	0.23795 (2)	0.870080 (14)	0.01613 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0132 (10)	0.0213 (11)	0.0250 (11)	0.0005 (8)	0.0060 (8)	−0.0015 (9)
C2	0.0125 (10)	0.0178 (11)	0.0182 (10)	0.0033 (8)	0.0030 (8)	−0.0001 (8)
C3	0.0138 (10)	0.0170 (10)	0.0175 (10)	−0.0015 (8)	0.0052 (8)	−0.0020 (8)
C4	0.0180 (10)	0.0161 (10)	0.0210 (10)	0.0003 (8)	0.0046 (8)	0.0028 (8)
C5	0.0161 (10)	0.0153 (10)	0.0185 (10)	0.0020 (8)	0.0039 (8)	0.0007 (8)
C6	0.0119 (10)	0.0168 (10)	0.0174 (10)	0.0010 (8)	0.0024 (8)	−0.0010 (8)
C7	0.0142 (10)	0.0184 (10)	0.0171 (10)	−0.0038 (8)	0.0057 (8)	−0.0022 (8)
C8	0.0133 (10)	0.0188 (11)	0.0284 (11)	−0.0023 (9)	0.0044 (9)	−0.0007 (9)
C9	0.0152 (10)	0.0137 (10)	0.0234 (10)	0.0012 (8)	0.0056 (8)	−0.0010 (8)
C10	0.0252 (12)	0.0360 (14)	0.0239 (11)	0.0017 (10)	0.0049 (10)	0.0073 (10)
C11	0.0267 (13)	0.0548 (18)	0.0270 (13)	0.0008 (12)	0.0000 (10)	0.0131 (12)
C12	0.0298 (14)	0.0624 (19)	0.0221 (12)	−0.0170 (13)	−0.0018 (10)	0.0036 (12)
C13	0.0300 (13)	0.0483 (16)	0.0196 (11)	−0.0168 (12)	0.0056 (10)	−0.0046 (11)
C14	0.0245 (12)	0.0306 (13)	0.0188 (11)	−0.0090 (10)	0.0070 (9)	−0.0028 (9)
C15	0.0444 (17)	0.0558 (18)	0.0243 (12)	−0.0224 (15)	0.0071 (12)	−0.0168 (12)
C16	0.0269 (12)	0.0262 (12)	0.0219 (11)	−0.0056 (10)	0.0107 (9)	−0.0048 (9)
C17	0.0540 (18)	0.0423 (17)	0.0350 (14)	−0.0205 (14)	0.0213 (13)	−0.0217 (12)
C18	0.0363 (14)	0.0304 (13)	0.0315 (13)	−0.0106 (11)	0.0185 (11)	−0.0100 (10)
C19	0.0492 (17)	0.0260 (13)	0.0501 (16)	−0.0004 (12)	0.0273 (14)	−0.0116 (12)
C20	0.0418 (15)	0.0285 (14)	0.0464 (16)	0.0112 (12)	0.0157 (13)	−0.0016 (12)
C21	0.0322 (14)	0.0299 (14)	0.0337 (13)	0.0068 (11)	0.0062 (11)	−0.0038 (11)
N1	0.0151 (9)	0.0175 (9)	0.0266 (9)	0.0037 (7)	0.0058 (7)	0.0038 (7)
N2	0.0122 (8)	0.0169 (9)	0.0230 (9)	−0.0003 (7)	0.0052 (7)	−0.0012 (7)
N3	0.0179 (9)	0.0298 (11)	0.0179 (9)	−0.0026 (8)	0.0030 (7)	0.0025 (8)
N4	0.0235 (10)	0.0254 (10)	0.0234 (9)	0.0014 (8)	0.0080 (8)	−0.0030 (8)
O1	0.0180 (8)	0.0454 (11)	0.0462 (11)	0.0108 (8)	0.0115 (8)	0.0256 (9)
O2	0.0198 (8)	0.0337 (9)	0.0343 (9)	0.0079 (7)	0.0149 (7)	0.0098 (7)
O3	0.0210 (8)	0.0329 (9)	0.0204 (8)	−0.0104 (7)	0.0030 (6)	0.0012 (7)
O4	0.0172 (7)	0.0199 (8)	0.0198 (7)	−0.0028 (6)	0.0036 (6)	0.0014 (6)
OW1	0.0139 (7)	0.0203 (8)	0.0216 (7)	−0.0007 (6)	0.0055 (6)	0.0004 (6)
OW2	0.0193 (8)	0.0442 (11)	0.0215 (8)	0.0020 (8)	0.0066 (7)	0.0014 (8)
OW3	0.101 (2)	0.0582 (16)	0.0250 (10)	0.0048 (13)	0.0016 (11)	−0.0050 (10)
OW4	0.057 (3)	0.031 (2)	0.053 (2)	0.0131 (19)	0.027 (2)	0.0075 (18)
Co1	0.01335 (15)	0.01823 (16)	0.01708 (14)	0.00037 (11)	0.00402 (10)	−0.00106 (11)

C1—N2	1.318 (3)	C15—C17	1.342 (4)
C1—N1	1.352 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—N4	1.360 (3)
C2—N1	1.387 (2)	C16—C18	1.414 (3)
C2—C4	1.395 (3)	C17—C18	1.439 (4)
C2—C3	1.402 (3)	C17—H17	0.9300
C3—C5	1.392 (3)	C18—C19	1.411 (4)
C3—N2	1.403 (2)	C19—C20	1.359 (4)
C4—C7	1.391 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.405 (3)
C5—C6	1.395 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—N4	1.327 (3)
C6—C7	1.415 (3)	C21—H21	0.9300
C6—C8	1.512 (3)	N1—H1A	0.8600
C7—C9	1.513 (3)	N2—Co1i	2.1304 (17)
C8—O2	1.250 (3)	N3—Co1	2.1412 (18)
C8—O1	1.264 (3)	N4—Co1	2.1478 (18)
C9—O3	1.259 (2)	O4—Co1	2.0582 (14)
C9—O4	1.263 (2)	OW1—Co1	2.1859 (15)
C10—N3	1.330 (3)	OW1—H1C	0.85
C10—C11	1.400 (3)	OW1—H1D	0.85
C10—H10	0.9300	OW2—Co1	2.0689 (16)
C11—C12	1.370 (4)	OW2—H2C	0.86
C11—H11	0.9300	OW2—H2D	0.83
C12—C13	1.409 (4)	OW3—H3C	0.87
C12—H12	0.9300	OW3—H3D	0.84
C13—C14	1.408 (3)	OW4—H4C	0.85
C13—C15	1.438 (4)	OW4—H4D	0.86
C14—N3	1.369 (3)	Co1—N2ii	2.1304 (17)
C14—C16	1.437 (3)
N2—C1—N1	113.57 (18)	C18—C17—H17	119.5
N2—C1—H1	123.2	C19—C18—C16	116.9 (2)
N1—C1—H1	123.2	C19—C18—C17	124.1 (2)
N1—C2—C4	132.52 (19)	C16—C18—C17	118.9 (2)
N1—C2—C3	105.23 (17)	C20—C19—C18	120.0 (2)
C4—C2—C3	122.24 (18)	C20—C19—H19	120.0
C5—C3—C2	120.06 (18)	C18—C19—H19	120.0
C5—C3—N2	130.47 (19)	C19—C20—C21	119.2 (2)
C2—C3—N2	109.46 (17)	C19—C20—H20	120.4
C7—C4—C2	117.49 (19)	C21—C20—H20	120.4
C7—C4—H4	121.3	N4—C21—C20	123.0 (2)
C2—C4—H4	121.3	N4—C21—H21	118.5
C3—C5—C6	118.51 (19)	C20—C21—H21	118.5
C3—C5—H5	120.7	C1—N1—C2	107.13 (17)
C6—C5—H5	120.7	C1—N1—H1A	126.4
C5—C6—C7	120.88 (18)	C2—N1—H1A	126.4
C5—C6—C8	117.26 (18)	C1—N2—C3	104.61 (17)
C7—C6—C8	121.72 (17)	C1—N2—Co1i	123.74 (14)
C4—C7—C6	120.81 (18)	C3—N2—Co1i	130.77 (13)
C4—C7—C9	116.55 (18)	C10—N3—C14	117.8 (2)
C6—C7—C9	122.64 (18)	C10—N3—Co1	128.73 (16)
O2—C8—O1	125.1 (2)	C14—N3—Co1	113.40 (14)
O2—C8—C6	118.34 (19)	C21—N4—C16	118.0 (2)
O1—C8—C6	116.54 (18)	C21—N4—Co1	128.41 (16)
O3—C9—O4	125.49 (19)	C16—N4—Co1	113.55 (15)
O3—C9—C7	119.11 (18)	C9—O4—Co1	130.78 (13)
O4—C9—C7	115.30 (18)	Co1—OW1—H1C	96
N3—C10—C11	123.2 (2)	Co1—OW1—H1D	116.4
N3—C10—H10	118.4	H1C—OW1—H1D	114.1
C11—C10—H10	118.4	Co1—OW2—H2C	114
C12—C11—C10	119.4 (2)	Co1—OW2—H2D	120.0
C12—C11—H11	120.3	H2C—OW2—H2D	113.4
C10—C11—H11	120.3	H3C—OW3—H3D	113.6
C11—C12—C13	119.3 (2)	H4C—OW4—H4D	114.7
C11—C12—H12	120.3	O4—Co1—OW2	176.10 (6)
C13—C12—H12	120.3	O4—Co1—N2ii	91.56 (6)
C14—C13—C12	117.7 (2)	OW2—Co1—N2ii	89.40 (7)
C14—C13—C15	118.7 (2)	O4—Co1—N3	91.15 (6)
C12—C13—C15	123.6 (2)	OW2—Co1—N3	92.41 (7)
N3—C14—C13	122.6 (2)	N2ii—Co1—N3	99.75 (7)
N3—C14—C16	117.51 (19)	O4—Co1—N4	88.60 (6)
C13—C14—C16	119.9 (2)	OW2—Co1—N4	90.59 (7)
C17—C15—C13	121.7 (2)	N2ii—Co1—N4	177.70 (7)
C17—C15—H15	119.1	N3—Co1—N4	77.95 (7)
C13—C15—H15	119.1	O4—Co1—OW1	90.32 (6)
N4—C16—C18	122.8 (2)	OW2—Co1—OW1	85.92 (6)
N4—C16—C14	117.5 (2)	N2ii—Co1—OW1	89.04 (6)
C18—C16—C14	119.7 (2)	N3—Co1—OW1	171.05 (6)
C15—C17—C18	121.0 (2)	N4—Co1—OW1	93.26 (6)
C15—C17—H17	119.5

D—H···A	D—H	H···A	D···A	D—H···A
OW1—H1C···O3	0.85	1.83	2.650 (2)	160
OW2—H2D···OW3	0.83	1.88	2.693 (2)	164
N1—H1A···OW1iii	0.86	2.05	2.837 (2)	151
OW1—H1D···O2iv	0.85	1.82	2.654 (2)	168
OW2—H2C···O1iv	0.86	1.77	2.619 (2)	172 (3)
OW3—H3C···O3v	0.87	1.92	2.726 (3)	155 (3)
OW3—H3D···OW4vi	0.84	2.38	2.940 (5)	125
OW4—H4C···OW3vii	0.85	2.10	2.891 (4)	154 (5)
OW4—H4C···OW2vii	0.85	2.54	3.166 (4)	131 (5)
OW4—H4D···O1ii	0.86	2.06	2.837 (4)	151

Table 1

Selected bond lengths (Å)

N2—Co1i	2.1304 (17)
N3—Co1	2.1412 (18)
N4—Co1	2.1478 (18)
O4—Co1	2.0582 (14)
OW1—Co1	2.1859 (15)
OW2—Co1	2.0689 (16)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW1—H1C⋯O3	0.85	1.83	2.650 (2)	160
OW2—H2D⋯OW3	0.83	1.88	2.693 (2)	164
N1—H1A⋯OW1iii	0.86	2.05	2.837 (2)	151
OW1—H1D⋯O2iv	0.85	1.82	2.654 (2)	168
OW2—H2C⋯O1iv	0.86	1.77	2.619 (2)	172 (3)
OW3—H3C⋯O3v	0.87	1.92	2.726 (3)	155 (3)
OW3—H3D⋯OW4vi	0.84	2.38	2.940 (5)	125
OW4—H4C⋯OW3vii	0.85	2.10	2.891 (4)	154 (5)
OW4—H4C⋯OW2vii	0.85	2.54	3.166 (4)	131 (5)
OW4—H4D⋯O1ii	0.86	2.06	2.837 (4)	151

Symmetry codes: (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .