Tetra-aqua-bis-(1H-benzimidazole-5,6-di-carboxyl-ato-κN)cobalt(II) dimethyl-formamide disolvate dihydrate.

In the mononuclear title compound, [Co(C(9)H(4)N(2)O(4))(2)(H(2)O)(4)]·2C(3)H(7)NO·2H(2)O, the Co(II) atom, which lies on a center of inversion, is coordinated by four water mol-ecules and two N atoms from two two symmetry-related 1H-benzimidazole-5,6-dicarboxyl-ate ligands in a distorted octa-hedral geometry. The packing is governed by inter-molecular O-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

Related literature

For 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Song et al. (2009a ▶,b ▶,c ▶).

Experimental

Crystal data

[Co(C9H5N2O4)2(H2O)4]·2C3H7NO·2H2O

M = 723.52

Triclinic,

a = 8.5612 (17) Å

b = 9.1475 (18) Å

c = 11.642 (2) Å

α = 100.82 (3)°

β = 102.98 (3)°

γ = 114.11 (3)°

V = 769.9 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.64 mm−1

T = 293 K

0.30 × 0.24 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.831, T max = 0.877

6161 measured reflections

2751 independent reflections

2594 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.127

S = 0.96

2751 reflections

219 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.44 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043177/ng2669sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043177/ng2669Isup2.hkl

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

[Co(C9H5N2O4)2(H2O)4]·2C3H7NO·2H2O	Z = 1
Mr = 723.52	F(000) = 377
Triclinic, P1	Dx = 1.561 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5612 (17) Å	Cell parameters from 3420 reflections
b = 9.1475 (18) Å	θ = 3.3–27.4°
c = 11.642 (2) Å	µ = 0.64 mm−1
α = 100.82 (3)°	T = 293 K
β = 102.98 (3)°	Block, red
γ = 114.11 (3)°	0.30 × 0.24 × 0.21 mm
V = 769.9 (3) Å3

Rigaku/MSC Mercury CCD diffractometer	2751 independent reflections
Radiation source: fine-focus sealed tube	2594 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 25.2°, θmin = 3.3°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −10→10
Tmin = 0.831, Tmax = 0.877	k = −10→10
6161 measured reflections	l = −13→13

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) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0795P)2 + 1.194P] where P = (Fo2 + 2Fc2)/3
2751 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.58 e Å−3
10 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.1417 (4)	0.8422 (3)	0.1200 (2)	0.0279 (6)
C2	0.2484 (3)	0.8904 (3)	0.2467 (2)	0.0247 (5)
C3	0.1906 (3)	0.7887 (3)	0.3191 (2)	0.0269 (5)
H3	0.2595	0.8201	0.4020	0.032*
C4	0.0277 (3)	0.6389 (3)	0.2654 (2)	0.0248 (5)
C5	−0.0742 (3)	0.5940 (3)	0.1405 (2)	0.0272 (6)
C6	−0.0194 (4)	0.6932 (4)	0.0667 (2)	0.0309 (6)
H6	−0.0888	0.6606	−0.0163	0.037*
C7	0.1921 (4)	0.9449 (4)	0.0363 (3)	0.0324 (6)
C8	0.4297 (3)	1.0478 (3)	0.3103 (2)	0.0263 (5)
C9	−0.2117 (4)	0.4034 (3)	0.2225 (3)	0.0310 (6)
H9	−0.2984	0.3064	0.2299	0.037*
C10	0.6732 (4)	0.7964 (4)	0.1713 (3)	0.0344 (6)
H10	0.7801	0.8972	0.1955	0.041*
N3	0.6382 (3)	0.7242 (3)	0.2550 (2)	0.0340 (5)
Co1	0.0000	0.5000	0.5000	0.02238 (18)
N1	−0.2262 (3)	0.4426 (3)	0.1168 (2)	0.0315 (5)
H1	−0.3137	0.3846	0.0473	0.038*
N2	−0.0630 (3)	0.5150 (3)	0.3148 (2)	0.0282 (5)
C12	0.4674 (5)	0.5710 (5)	0.2251 (4)	0.0552 (9)
H3A	0.3742	0.6008	0.2330	0.083*
H3B	0.4829	0.5094	0.2812	0.083*
H3C	0.4330	0.5021	0.1414	0.083*
C11	0.7568 (6)	0.8059 (5)	0.3848 (3)	0.0547 (9)
H4A	0.8640	0.9036	0.3911	0.082*
H4B	0.7907	0.7283	0.4145	0.082*
H4C	0.6937	0.8393	0.4340	0.082*
O1	0.1079 (3)	0.8972 (3)	−0.0726 (2)	0.0582 (7)
O2	0.3337 (4)	1.0933 (3)	0.0904 (2)	0.0635 (8)
O3	0.4308 (3)	1.1767 (3)	0.3708 (2)	0.0458 (6)
O4	0.5660 (3)	1.0359 (3)	0.3035 (3)	0.0524 (6)
O5	0.5725 (3)	0.7391 (3)	0.06005 (19)	0.0457 (6)
O1W	0.0884 (2)	0.7574 (2)	0.57397 (17)	0.0300 (4)
H2W	0.0296	0.7784	0.6176	0.045*
H1W	0.2007	0.8133	0.6126	0.045*
O2W	0.2619 (3)	0.5455 (2)	0.50191 (19)	0.0360 (5)
H4W	0.2576	0.4881	0.4347	0.054*
H3W	0.3630	0.6321	0.5381	0.054*
O3W	0.1590 (3)	0.2539 (3)	0.3083 (2)	0.0498 (6)
H5W	0.2452	0.2312	0.3275	0.075*
H6W	0.0905	0.2004	0.2343	0.075*
H2	0.367 (6)	1.146 (5)	0.041 (3)	0.075*

	U11	U22	U33	U12	U13	U23
C1	0.0271 (13)	0.0262 (13)	0.0258 (13)	0.0076 (11)	0.0094 (10)	0.0090 (10)
C2	0.0231 (12)	0.0223 (12)	0.0259 (13)	0.0076 (10)	0.0088 (10)	0.0076 (10)
C3	0.0258 (13)	0.0260 (13)	0.0217 (12)	0.0073 (11)	0.0052 (10)	0.0071 (10)
C4	0.0247 (12)	0.0238 (12)	0.0245 (12)	0.0089 (10)	0.0098 (10)	0.0089 (10)
C5	0.0248 (13)	0.0230 (13)	0.0260 (13)	0.0052 (11)	0.0080 (10)	0.0062 (10)
C6	0.0303 (14)	0.0302 (14)	0.0224 (13)	0.0067 (12)	0.0060 (11)	0.0082 (11)
C7	0.0322 (14)	0.0304 (14)	0.0262 (14)	0.0071 (12)	0.0081 (11)	0.0111 (11)
C8	0.0232 (13)	0.0248 (13)	0.0257 (13)	0.0066 (11)	0.0064 (10)	0.0101 (11)
C9	0.0277 (14)	0.0244 (13)	0.0306 (14)	0.0026 (11)	0.0088 (11)	0.0103 (11)
C10	0.0334 (15)	0.0294 (14)	0.0290 (14)	0.0074 (12)	0.0047 (12)	0.0088 (11)
N3	0.0404 (13)	0.0350 (13)	0.0270 (12)	0.0174 (11)	0.0105 (10)	0.0122 (10)
Co1	0.0203 (3)	0.0186 (3)	0.0219 (3)	0.0040 (2)	0.00591 (19)	0.00645 (19)
N1	0.0243 (11)	0.0260 (12)	0.0229 (11)	−0.0027 (9)	0.0002 (9)	0.0055 (9)
N2	0.0271 (11)	0.0238 (11)	0.0262 (11)	0.0046 (9)	0.0083 (9)	0.0097 (9)
C12	0.052 (2)	0.057 (2)	0.060 (2)	0.0169 (18)	0.0275 (18)	0.0332 (18)
C11	0.085 (3)	0.055 (2)	0.0270 (16)	0.041 (2)	0.0084 (16)	0.0138 (15)
O1	0.0560 (15)	0.0498 (14)	0.0286 (11)	−0.0072 (11)	−0.0002 (10)	0.0191 (10)
O2	0.0580 (15)	0.0463 (14)	0.0325 (12)	−0.0183 (12)	−0.0036 (11)	0.0210 (11)
O3	0.0293 (11)	0.0302 (11)	0.0569 (14)	0.0051 (9)	0.0109 (10)	−0.0062 (10)
O4	0.0218 (10)	0.0340 (12)	0.0823 (18)	0.0077 (9)	0.0093 (11)	−0.0002 (11)
O5	0.0399 (12)	0.0433 (12)	0.0270 (11)	−0.0014 (10)	0.0014 (9)	0.0144 (9)
O1W	0.0238 (9)	0.0245 (9)	0.0318 (10)	0.0058 (8)	0.0057 (8)	0.0051 (8)
O2W	0.0250 (10)	0.0296 (10)	0.0399 (11)	0.0049 (8)	0.0114 (8)	0.0004 (8)
O3W	0.0428 (13)	0.0590 (15)	0.0395 (12)	0.0271 (12)	0.0088 (10)	−0.0033 (11)

C1—C6	1.381 (4)	N3—C12	1.462 (4)
C1—C2	1.424 (4)	N3—C11	1.463 (4)
C1—C7	1.489 (4)	Co1—O1W	2.086 (2)
C2—C3	1.387 (4)	Co1—O1Wi	2.086 (2)
C2—C8	1.513 (4)	Co1—O2Wi	2.1007 (19)
C3—C4	1.393 (4)	Co1—O2W	2.1007 (19)
C3—H3	0.9300	Co1—N2	2.146 (2)
C4—N2	1.395 (3)	Co1—N2i	2.146 (2)
C4—C5	1.398 (4)	N1—H1	0.8600
C5—C6	1.382 (4)	C12—H3A	0.9600
C5—N1	1.382 (3)	C12—H3B	0.9600
C6—H6	0.9300	C12—H3C	0.9600
C7—O1	1.201 (4)	C11—H4A	0.9600
C7—O2	1.304 (4)	C11—H4B	0.9600
C8—O4	1.234 (3)	C11—H4C	0.9600
C8—O3	1.250 (3)	O2—H2	0.839 (10)
C9—N2	1.315 (4)	O1W—H2W	0.8400
C9—N1	1.338 (4)	O1W—H1W	0.8400
C9—H9	0.9300	O2W—H4W	0.8399
C10—O5	1.253 (3)	O2W—H3W	0.8399
C10—N3	1.299 (4)	O3W—H5W	0.8400
C10—H10	0.9300	O3W—H6W	0.8399
C6—C1—C2	120.8 (2)	O1Wi—Co1—O2W	88.64 (8)
C6—C1—C7	115.4 (2)	O2Wi—Co1—O2W	180.0
C2—C1—C7	123.8 (2)	O1W—Co1—N2	90.82 (9)
C3—C2—C1	120.3 (2)	O1Wi—Co1—N2	89.18 (9)
C3—C2—C8	115.8 (2)	O2Wi—Co1—N2	90.29 (9)
C1—C2—C8	123.9 (2)	O2W—Co1—N2	89.71 (9)
C2—C3—C4	118.9 (2)	O1W—Co1—N2i	89.18 (9)
C2—C3—H3	120.6	O1Wi—Co1—N2i	90.82 (9)
C4—C3—H3	120.6	O2Wi—Co1—N2i	89.71 (9)
C3—C4—N2	131.3 (2)	O2W—Co1—N2i	90.29 (9)
C3—C4—C5	119.7 (2)	N2—Co1—N2i	179.999 (1)
N2—C4—C5	108.9 (2)	C9—N1—C5	107.1 (2)
C6—C5—N1	132.1 (2)	C9—N1—H1	126.5
C6—C5—C4	122.4 (2)	C5—N1—H1	126.5
N1—C5—C4	105.5 (2)	C9—N2—C4	104.9 (2)
C1—C6—C5	117.9 (2)	C9—N2—Co1	124.00 (18)
C1—C6—H6	121.0	C4—N2—Co1	130.98 (18)
C5—C6—H6	121.0	N3—C12—H3A	109.5
O1—C7—O2	121.9 (3)	N3—C12—H3B	109.5
O1—C7—C1	123.1 (3)	H3A—C12—H3B	109.5
O2—C7—C1	115.0 (2)	N3—C12—H3C	109.5
O4—C8—O3	125.2 (3)	H3A—C12—H3C	109.5
O4—C8—C2	117.0 (2)	H3B—C12—H3C	109.5
O3—C8—C2	117.7 (2)	N3—C11—H4A	109.5
N2—C9—N1	113.6 (2)	N3—C11—H4B	109.5
N2—C9—H9	123.2	H4A—C11—H4B	109.5
N1—C9—H9	123.2	N3—C11—H4C	109.5
O5—C10—N3	124.3 (3)	H4A—C11—H4C	109.5
O5—C10—H10	117.8	H4B—C11—H4C	109.5
N3—C10—H10	117.8	C7—O2—H2	114 (3)
C10—N3—C12	120.6 (3)	Co1—O1W—H2W	113.1
C10—N3—C11	120.7 (3)	Co1—O1W—H1W	113.3
C12—N3—C11	118.2 (3)	H2W—O1W—H1W	110.9
O1W—Co1—O1Wi	180.0	Co1—O2W—H4W	110.8
O1W—Co1—O2Wi	88.64 (8)	Co1—O2W—H3W	130.9
O1Wi—Co1—O2Wi	91.36 (8)	H4W—O2W—H3W	112.2
O1W—Co1—O2W	91.36 (8)	H5W—O3W—H6W	112.2

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ii	0.84 (1)	1.75 (1)	2.588 (3)	177 (5)
O3W—H6W···O1iii	0.84	1.98	2.800 (3)	165
O3W—H5W···O3iv	0.84	1.85	2.686 (3)	179
O2W—H3W···O3v	0.84	1.80	2.636 (3)	174
O2W—H4W···O3W	0.84	2.06	2.811 (3)	148
O1W—H1W···O4v	0.84	1.79	2.624 (3)	170
O1W—H2W···O3Wi	0.84	1.94	2.749 (3)	161
N1—H1···O5iii	0.86	1.98	2.782 (3)	154
N1—H1···O5iii	0.86	1.98	2.782 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5i	0.839 (10)	1.750 (11)	2.588 (3)	177 (5)
O3W—H6W⋯O1ii	0.84	1.98	2.800 (3)	165
O3W—H5W⋯O3iii	0.84	1.85	2.686 (3)	179
O2W—H3W⋯O3iv	0.84	1.80	2.636 (3)	174
O2W—H4W⋯O3W	0.84	2.06	2.811 (3)	148
O1W—H1W⋯O4iv	0.84	1.79	2.624 (3)	170
O1W—H2W⋯O3Wv	0.84	1.94	2.749 (3)	161
N1—H1⋯O5ii	0.86	1.98	2.782 (3)	154
N1—H1⋯O5ii	0.86	1.98	2.782 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .