Tetra-aquabis(6-carboxy-1H-benzimid-azole-5-carboxyl-ato-κN)nickel(II) dimethyl-formamide disolvate dihydrate.

The title compound, [Ni(C(9)H(45)N(2)O(4))(2)(H(2)O)(4)]·2C(3)H(7)NO·2H(2)O, has the Ni(II) center coordinated by four water mol-ecules and two N atoms from two 1H-benzimidazole-5,6-dicarboxyl-ate ligands in an octa-hedral geometry. The mol-ecule inter-acts with the solvent water and dimethyl-formamide mol-ecules through N-H⋯O and O-H⋯O hydrogen bonds to form a three-dimensional supra-molecular network. The metal atom lies on a center of inversion.

Related literature

For the crystal structures of 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Gao et al. (2008 ▶); Lo et al. (2007 ▶); Song et al. (2009 ▶).

Experimental

Crystal data

[Ni(C9H5N2O4)2(H2O)4]·2C3H7NO·2H2O

M = 723.30

Triclinic,

a = 8.5327 (17) Å

b = 9.1387 (18) Å

c = 11.624 (2) Å

α = 100.80 (3)°

β = 103.03 (3)°

γ = 114.04 (3)°

V = 765.7 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.72 mm−1

T = 293 K

0.27 × 0.18 × 0.17 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.830, T max = 0.888

6116 measured reflections

2737 independent reflections

2613 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.137

S = 1.20

2737 reflections

217 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.32 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: SHELXL9.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038069/ng2646sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038069/ng2646Isup2.hkl

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

[Ni(C9H5N2O4)2(H2O)4]·2C3H7NO·2H2O	Z = 1
Mr = 723.30	F(000) = 378
Triclinic, P1	Dx = 1.569 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5327 (17) Å	Cell parameters from 3600 reflections
b = 9.1387 (18) Å	θ = 1.4–28°
c = 11.624 (2) Å	µ = 0.72 mm−1
α = 100.80 (3)°	T = 293 K
β = 103.03 (3)°	Block, green
γ = 114.04 (3)°	0.27 × 0.18 × 0.17 mm
V = 765.7 (3) Å3

Rigaku/MSC Mercury CCD diffractometer	2737 independent reflections
Radiation source: fine-focus sealed tube	2613 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 = 0.830, Tmax = 0.888	k = −10→9
6116 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.1051P)2 + 0.01P] where P = (Fo2 + 2Fc2)/3
2737 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.61 e Å−3
9 restraints	Δρmin = −0.32 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	0.2895 (3)	0.4030 (3)	0.2261 (2)	0.0301 (5)
H1	0.2030	0.3062	0.2339	0.036*
N1	0.4387 (2)	0.5153 (2)	0.31852 (17)	0.0272 (4)
Ni1	0.5000	0.5000	0.5000	0.02200 (19)
C2	0.4271 (3)	0.5938 (3)	0.1432 (2)	0.0272 (5)
N2	0.2739 (2)	0.4415 (2)	0.11945 (17)	0.0324 (4)
H2	0.1861	0.3832	0.0499	0.039*
C3	0.5296 (3)	0.6391 (3)	0.2686 (2)	0.0252 (4)
O3W	0.75996 (16)	0.54366 (16)	0.50333 (12)	0.0345 (4)
C4	0.6923 (3)	0.7892 (3)	0.3224 (2)	0.0271 (5)
H4	0.7612	0.8210	0.4056	0.033*
C5	0.7498 (3)	0.8909 (3)	0.2494 (2)	0.0248 (4)
O1	0.9319 (2)	1.1775 (2)	0.37262 (18)	0.0456 (5)
C6	0.6429 (3)	0.8423 (3)	0.1223 (2)	0.0280 (5)
O2	1.0690 (2)	1.0376 (2)	0.3063 (2)	0.0522 (5)
C7	0.4811 (3)	0.6925 (3)	0.0690 (2)	0.0307 (5)
H7	0.4113	0.6596	−0.0141	0.037*
C8	0.6944 (3)	0.9451 (3)	0.0384 (2)	0.0327 (5)
C9	0.9321 (3)	1.0500 (3)	0.31293 (19)	0.0261 (5)
O2W	0.41483 (16)	0.24688 (15)	0.42925 (12)	0.0295 (4)
H6W	0.8553	0.6369	0.5347	0.044*
H5W	0.7568	0.4874	0.4361	0.044*
H3W	0.4755	0.2330	0.3845	0.044*
H4W	0.3028	0.1830	0.3922	0.044*
O3	0.6082 (3)	0.8962 (3)	−0.07127 (17)	0.0591 (6)
O4	0.8343 (3)	1.0927 (3)	0.09199 (18)	0.0633 (7)
H4A	0.8481	1.1446	0.0415	0.095*
O1W	0.3424 (2)	0.7464 (3)	0.69171 (17)	0.0487 (5)
H1W	0.3996	0.7866	0.7687	0.073*
H2W	0.2637	0.7784	0.6716	0.073*
O5	0.0718 (2)	0.7407 (2)	0.05904 (16)	0.0462 (5)
C12	−0.0319 (4)	0.5721 (4)	0.2255 (3)	0.0570 (8)
H12A	−0.1264	0.6015	0.2316	0.086*
H12B	−0.0161	0.5128	0.2835	0.086*
H12C	−0.0653	0.5013	0.1426	0.086*
N3	0.1376 (3)	0.7248 (3)	0.25427 (18)	0.0352 (5)
C11	0.2581 (4)	0.8066 (4)	0.3847 (2)	0.0522 (7)
H11A	0.3625	0.9074	0.3914	0.078*
H11B	0.2971	0.7308	0.4129	0.078*
H11C	0.1933	0.8351	0.4351	0.078*
C10	0.1722 (3)	0.7970 (3)	0.1704 (2)	0.0356 (5)
H10	0.2794	0.8978	0.1949	0.043*

	U11	U22	U33	U12	U13	U23
C1	0.0264 (11)	0.0250 (11)	0.0280 (11)	0.0029 (9)	0.0068 (9)	0.0092 (9)
N1	0.0272 (9)	0.0227 (9)	0.0259 (9)	0.0057 (7)	0.0082 (7)	0.0098 (7)
Ni1	0.0196 (3)	0.0191 (3)	0.0217 (3)	0.00424 (18)	0.00625 (17)	0.00652 (17)
C2	0.0216 (10)	0.0230 (10)	0.0262 (11)	0.0024 (8)	0.0062 (8)	0.0055 (9)
N2	0.0256 (9)	0.0274 (10)	0.0254 (9)	−0.0008 (8)	0.0021 (7)	0.0071 (8)
C3	0.0242 (10)	0.0248 (10)	0.0264 (11)	0.0093 (8)	0.0112 (8)	0.0099 (9)
O3W	0.0231 (8)	0.0295 (8)	0.0380 (9)	0.0049 (6)	0.0105 (6)	0.0003 (7)
C4	0.0231 (10)	0.0266 (11)	0.0223 (10)	0.0059 (8)	0.0037 (8)	0.0060 (8)
C5	0.0223 (10)	0.0237 (11)	0.0245 (10)	0.0075 (8)	0.0074 (8)	0.0078 (8)
O1	0.0282 (9)	0.0305 (9)	0.0559 (11)	0.0043 (7)	0.0102 (7)	−0.0071 (8)
C6	0.0252 (10)	0.0278 (11)	0.0258 (11)	0.0073 (9)	0.0082 (8)	0.0098 (9)
O2	0.0233 (9)	0.0324 (9)	0.0833 (15)	0.0073 (7)	0.0126 (8)	0.0002 (9)
C7	0.0283 (11)	0.0312 (11)	0.0217 (10)	0.0069 (9)	0.0037 (8)	0.0072 (9)
C8	0.0295 (11)	0.0328 (12)	0.0266 (12)	0.0063 (9)	0.0078 (9)	0.0113 (10)
C9	0.0220 (10)	0.0249 (11)	0.0249 (11)	0.0059 (9)	0.0050 (8)	0.0095 (9)
O2W	0.0250 (7)	0.0233 (7)	0.0316 (8)	0.0058 (6)	0.0076 (6)	0.0054 (6)
O3	0.0561 (12)	0.0527 (12)	0.0269 (9)	−0.0082 (9)	0.0002 (8)	0.0191 (9)
O4	0.0599 (12)	0.0464 (11)	0.0327 (10)	−0.0161 (9)	−0.0030 (9)	0.0224 (9)
O1W	0.0396 (10)	0.0590 (12)	0.0390 (10)	0.0258 (9)	0.0087 (8)	−0.0036 (9)
O5	0.0409 (10)	0.0468 (10)	0.0272 (9)	0.0019 (8)	0.0025 (7)	0.0156 (8)
C12	0.0560 (17)	0.0591 (18)	0.0607 (19)	0.0195 (14)	0.0312 (15)	0.0326 (15)
N3	0.0421 (11)	0.0367 (11)	0.0260 (10)	0.0184 (9)	0.0101 (9)	0.0103 (9)
C11	0.078 (2)	0.0531 (17)	0.0285 (13)	0.0379 (16)	0.0077 (13)	0.0140 (12)
C10	0.0363 (12)	0.0301 (12)	0.0302 (12)	0.0083 (10)	0.0065 (10)	0.0104 (10)

C1—N1	1.317 (3)	C6—C7	1.386 (3)
C1—N2	1.344 (3)	C6—C8	1.492 (3)
C1—H1	0.9300	O2—C9	1.236 (3)
N1—C3	1.397 (3)	C7—H7	0.9300
N1—Ni1	2.1014 (18)	C8—O3	1.209 (3)
Ni1—O2W	2.0501 (14)	C8—O4	1.293 (3)
Ni1—O2Wi	2.0501 (14)	O2W—H3W	0.8401
Ni1—O3Wi	2.0773 (13)	O2W—H4W	0.8400
Ni1—O3W	2.0773 (13)	O4—H4A	0.8200
Ni1—N1i	2.1014 (18)	O1W—H1W	0.8408
C2—C7	1.379 (3)	O1W—H2W	0.8405
C2—N2	1.390 (3)	O5—C10	1.252 (3)
C2—C3	1.401 (3)	C12—N3	1.454 (4)
N2—H2	0.8600	C12—H12A	0.9600
C3—C4	1.391 (3)	C12—H12B	0.9600
O3W—H6W	0.8402	C12—H12C	0.9600
O3W—H5W	0.8394	N3—C10	1.298 (3)
C4—C5	1.391 (3)	N3—C11	1.470 (3)
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.424 (3)	C11—H11B	0.9600
C5—C9	1.522 (3)	C11—H11C	0.9600
O1—C9	1.240 (3)	C10—H10	0.9300
N1—C1—N2	113.71 (18)	C4—C5—C9	115.96 (18)
N1—C1—H1	123.1	C6—C5—C9	123.63 (19)
N2—C1—H1	123.1	C7—C6—C5	120.7 (2)
C1—N1—C3	104.99 (18)	C7—C6—C8	115.74 (19)
C1—N1—Ni1	123.63 (15)	C5—C6—C8	123.59 (19)
C3—N1—Ni1	131.30 (15)	C2—C7—C6	117.85 (19)
O2W—Ni1—O2Wi	180.0	C2—C7—H7	121.1
O2W—Ni1—O3Wi	91.85 (6)	C6—C7—H7	121.1
O2Wi—Ni1—O3Wi	88.15 (6)	O3—C8—O4	122.2 (2)
O2W—Ni1—O3W	88.15 (6)	O3—C8—C6	122.5 (2)
O2Wi—Ni1—O3W	91.85 (6)	O4—C8—C6	115.3 (2)
O3Wi—Ni1—O3W	180.0	O2—C9—O1	125.6 (2)
O2W—Ni1—N1i	90.06 (7)	O2—C9—C5	116.7 (2)
O2Wi—Ni1—N1i	89.94 (7)	O1—C9—C5	117.58 (18)
O3Wi—Ni1—N1i	90.14 (7)	Ni1—O2W—H3W	109.0
O3W—Ni1—N1i	89.86 (7)	Ni1—O2W—H4W	117.7
O2W—Ni1—N1	89.94 (7)	H3W—O2W—H4W	110.9
O2Wi—Ni1—N1	90.06 (7)	C8—O4—H4A	109.5
O3Wi—Ni1—N1	89.86 (7)	H1W—O1W—H2W	111.4
O3W—Ni1—N1	90.14 (7)	N3—C12—H12A	109.5
N1i—Ni1—N1	180.0	N3—C12—H12B	109.5
C7—C2—N2	131.9 (2)	H12A—C12—H12B	109.5
C7—C2—C3	122.56 (19)	N3—C12—H12C	109.5
N2—C2—C3	105.48 (19)	H12A—C12—H12C	109.5
C1—N2—C2	106.79 (18)	H12B—C12—H12C	109.5
C1—N2—H2	126.6	C10—N3—C12	121.1 (2)
C2—N2—H2	126.6	C10—N3—C11	120.7 (2)
C4—C3—N1	131.2 (2)	C12—N3—C11	117.8 (2)
C4—C3—C2	119.76 (19)	N3—C11—H11A	109.5
N1—C3—C2	109.02 (19)	N3—C11—H11B	109.5
Ni1—O3W—H6W	126.3	H11A—C11—H11B	109.5
Ni1—O3W—H5W	111.1	N3—C11—H11C	109.5
H6W—O3W—H5W	111.6	H11A—C11—H11C	109.5
C5—C4—C3	118.77 (19)	H11B—C11—H11C	109.5
C5—C4—H4	120.6	O5—C10—N3	124.8 (2)
C3—C4—H4	120.6	O5—C10—H10	117.6
C4—C5—C6	120.39 (19)	N3—C10—H10	117.6

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O1ii	0.84	1.86	2.693 (3)	173
O1W—H1W···O3iii	0.84	2.00	2.801 (3)	160
O4—H4A···O5iv	0.82	1.78	2.585 (3)	167
O2W—H4W···O2v	0.84	1.79	2.624 (3)	176
O2W—H3W···O1Wi	0.84	1.92	2.741 (2)	166
O3W—H5W···O1Wi	0.84	2.06	2.810 (3)	148
O3W—H6W···O1vi	0.84	1.81	2.634 (3)	169
N2—H2···O5vii	0.86	1.98	2.779 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O1i	0.84	1.86	2.693 (3)	173
O1W—H1W⋯O3ii	0.84	2.00	2.801 (3)	160
O4—H4A⋯O5iii	0.82	1.78	2.585 (3)	167
O2W—H4W⋯O2iv	0.84	1.79	2.624 (3)	176
O2W—H3W⋯O1Wv	0.84	1.92	2.741 (2)	166
O3W—H5W⋯O1Wv	0.84	2.06	2.810 (3)	148
O3W—H6W⋯O1vi	0.84	1.81	2.634 (3)	169
N2—H2⋯O5vii	0.86	1.98	2.779 (3)	155

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