Penta-aqua-(1H-benzimidazole-5,6-dicarboxyl-ato-κN)nickel(II) penta-hydrate.

In the title mononuclear complex, [Ni(C(9)H(4)N(2)O(4))(H(2)O)(5)]·5H(2)O, the Ni(II) atom is six-coordinated by one N atom from a 1H-benzimidazole-5,6-dicarboxyl-ate ligand and by five O atoms from five water mol-ecules and displays a distorted octa-hedral geometry. Inter-molecular O-H⋯O hydrogen-bonding inter-actions among the coordinated water mol-ecules, solvent water mol-ecules and carboxyl O atoms of the organic ligand and additional N-H⋯O hydrogen bonding lead to the formation of a three-dimensional supra-molecular network.

Related literature

For background information on 1H-benzimidazole-5,6-dicarboxyl­ate complexes, see: Lo et al. (2007 ▶); Yao et al. (2008 ▶).

Experimental

Crystal data

[Ni(C9H4N2O4)(H2O)5]·5H2O

M = 443.01

Triclinic,

a = 6.8436 (14) Å

b = 11.434 (2) Å

c = 12.344 (3) Å

α = 78.29 (3)°

β = 78.65 (3)°

γ = 74.92 (3)°

V = 902.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.15 mm−1

T = 293 K

0.31 × 0.25 × 0.21 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.725, T max = 0.793

7176 measured reflections

3228 independent reflections

2851 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.167

S = 1.14

3228 reflections

235 parameters

30 restraints

H-atom parameters constrained

Δρmax = 1.53 e Å−3

Δρmin = −0.60 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/S1600536809018704/zl2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018704/zl2208Isup2.hkl

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

[Ni(C9H4N2O4)(H2O)5]·5H2O	Z = 2
Mr = 443.01	F(000) = 464
Triclinic, P1	Dx = 1.630 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8436 (14) Å	Cell parameters from 3600 reflections
b = 11.434 (2) Å	θ = 1.4–28°
c = 12.344 (3) Å	µ = 1.15 mm−1
α = 78.29 (3)°	T = 293 K
β = 78.65 (3)°	Block, blue
γ = 74.92 (3)°	0.31 × 0.25 × 0.21 mm
V = 902.6 (3) Å3

Rigaku Mercury CCD diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	2851 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 25.2°, θmin = 3.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −8→8
Tmin = 0.725, Tmax = 0.793	k = −13→13
7176 measured reflections	l = −14→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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0905P)2 + 1.2897P] where P = (Fo2 + 2Fc2)/3
3228 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 1.53 e Å−3
30 restraints	Δρmin = −0.60 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	0.3714 (6)	0.5621 (4)	0.7112 (3)	0.0205 (8)
N1	0.3498 (6)	0.3063 (3)	0.9967 (3)	0.0272 (8)
H1	0.3074	0.3078	1.0669	0.033*
Ni1	0.59930 (7)	0.09723 (4)	0.74101 (4)	0.0200 (2)
O1	0.2171 (5)	0.6926 (3)	0.5614 (3)	0.0379 (8)
C2	0.4484 (6)	0.4375 (3)	0.7118 (3)	0.0210 (8)
H2	0.5106	0.4068	0.6460	0.025*
N2	0.4903 (5)	0.2318 (3)	0.8396 (3)	0.0224 (7)
O2	0.5536 (5)	0.6543 (3)	0.5459 (2)	0.0346 (8)
C3	0.4301 (6)	0.3595 (3)	0.8136 (3)	0.0209 (8)
O3	0.0491 (5)	0.7830 (3)	0.8792 (3)	0.0346 (8)
C4	0.3381 (6)	0.4072 (4)	0.9121 (3)	0.0230 (8)
O4	0.3074 (5)	0.8139 (3)	0.7441 (3)	0.0328 (7)
C5	0.2592 (6)	0.5316 (4)	0.9124 (3)	0.0253 (9)
H5	0.1973	0.5617	0.9785	0.030*
C6	0.2755 (6)	0.6096 (4)	0.8113 (3)	0.0222 (8)
C7	0.4385 (7)	0.2068 (4)	0.9496 (3)	0.0258 (9)
H7	0.4618	0.1277	0.9898	0.031*
C8	0.2025 (6)	0.7459 (4)	0.8107 (3)	0.0243 (9)
C9	0.3812 (6)	0.6449 (3)	0.5979 (3)	0.0217 (8)
O1W	0.3920 (4)	0.1803 (3)	0.6302 (2)	0.0284 (7)
H2W	0.4303	0.2272	0.5727	0.043*
H1W	0.3513	0.1237	0.6138	0.043*
O2W	0.8180 (4)	0.1821 (3)	0.6393 (2)	0.0274 (6)
H3W	0.8697	0.2273	0.6656	0.041*
H4W	0.7925	0.2129	0.5744	0.041*
O3W	0.7170 (6)	−0.0427 (3)	0.6518 (3)	0.0463 (10)
H5W	0.7472	−0.1164	0.6823	0.070*
H6W	0.7539	−0.0344	0.5822	0.070*
O4W	0.7928 (5)	0.0082 (3)	0.8549 (3)	0.0313 (7)
H7W	0.8647	−0.0596	0.8391	0.047*
H8W	0.8618	0.0475	0.8765	0.047*
O5W	0.3802 (5)	0.0021 (3)	0.8336 (2)	0.0285 (7)
H9W	0.2734	0.0489	0.8607	0.043*
H10W	0.3518	−0.0525	0.8072	0.043*
O6W	0.8012 (5)	0.9831 (3)	0.4213 (2)	0.0340 (7)
H11W	0.7615	1.0420	0.3717	0.051*
H12W	0.9257	0.9499	0.4049	0.051*
O7W	0.2893 (5)	0.2719 (3)	0.2313 (3)	0.0372 (8)
H14W	0.4128	0.2554	0.2398	0.056*
H13W	0.2201	0.3317	0.2624	0.056*
O8W	0.9187 (5)	0.5590 (3)	0.6314 (3)	0.0431 (8)
H16W	0.8200	0.5777	0.5952	0.065*
H15W	1.0137	0.5932	0.5982	0.065*
O9W	−0.0044 (5)	0.8476 (3)	0.0863 (3)	0.0378 (8)
H18W	0.0184	0.7895	0.1395	0.057*
H17W	0.0075	0.8220	0.0257	0.057*
O10W	0.0100 (5)	0.3191 (3)	0.7221 (3)	0.0406 (8)
H19W	−0.0044	0.3950	0.7006	0.061*
H20W	0.1257	0.2800	0.6958	0.061*

	U11	U22	U33	U12	U13	U23
C1	0.0213 (19)	0.021 (2)	0.0181 (18)	−0.0063 (15)	−0.0026 (15)	0.0000 (15)
N1	0.041 (2)	0.0185 (17)	0.0163 (16)	−0.0034 (14)	−0.0012 (15)	0.0021 (13)
Ni1	0.0245 (3)	0.0148 (3)	0.0184 (3)	−0.0027 (2)	−0.0024 (2)	−0.00091 (19)
O1	0.0319 (17)	0.0426 (19)	0.0323 (16)	−0.0088 (14)	−0.0108 (13)	0.0156 (14)
C2	0.025 (2)	0.0178 (19)	0.0179 (18)	−0.0028 (15)	−0.0014 (15)	−0.0019 (14)
N2	0.0285 (18)	0.0143 (16)	0.0211 (16)	−0.0028 (13)	−0.0034 (14)	0.0013 (12)
O2	0.0295 (16)	0.0383 (18)	0.0272 (16)	−0.0074 (13)	−0.0024 (13)	0.0123 (13)
C3	0.0221 (19)	0.0179 (19)	0.0218 (19)	−0.0035 (15)	−0.0035 (15)	−0.0023 (15)
O3	0.0371 (17)	0.0234 (16)	0.0344 (17)	0.0036 (13)	0.0036 (14)	−0.0068 (12)
C4	0.028 (2)	0.021 (2)	0.0189 (19)	−0.0063 (16)	−0.0015 (16)	−0.0002 (14)
O4	0.0382 (18)	0.0188 (15)	0.0391 (17)	−0.0077 (12)	−0.0007 (14)	−0.0031 (12)
C5	0.031 (2)	0.021 (2)	0.0205 (19)	−0.0028 (16)	−0.0002 (16)	−0.0037 (15)
C6	0.023 (2)	0.017 (2)	0.024 (2)	−0.0018 (15)	−0.0034 (16)	−0.0027 (15)
C7	0.035 (2)	0.0179 (19)	0.022 (2)	−0.0049 (16)	−0.0046 (17)	0.0015 (15)
C8	0.030 (2)	0.018 (2)	0.024 (2)	−0.0036 (16)	−0.0074 (17)	−0.0021 (15)
C9	0.030 (2)	0.0166 (19)	0.0192 (19)	−0.0058 (16)	−0.0053 (16)	−0.0015 (14)
O1W	0.0327 (16)	0.0282 (16)	0.0246 (14)	−0.0124 (12)	−0.0063 (12)	0.0039 (11)
O2W	0.0297 (15)	0.0283 (16)	0.0238 (14)	−0.0103 (12)	−0.0053 (12)	0.0023 (11)
O3W	0.081 (3)	0.0219 (16)	0.0287 (17)	−0.0075 (16)	0.0088 (17)	−0.0086 (13)
O4W	0.0315 (16)	0.0221 (15)	0.0396 (17)	0.0020 (12)	−0.0139 (13)	−0.0052 (12)
O5W	0.0327 (16)	0.0227 (15)	0.0292 (15)	−0.0092 (12)	0.0025 (12)	−0.0053 (11)
O6W	0.0355 (18)	0.0310 (17)	0.0306 (16)	−0.0042 (13)	−0.0035 (13)	0.0006 (12)
O7W	0.0381 (18)	0.0401 (19)	0.0320 (17)	−0.0067 (14)	−0.0040 (14)	−0.0067 (14)
O8W	0.0349 (18)	0.039 (2)	0.052 (2)	−0.0080 (15)	−0.0099 (15)	0.0024 (15)
O9W	0.0462 (19)	0.0365 (18)	0.0310 (16)	−0.0061 (15)	−0.0090 (15)	−0.0077 (13)
O10W	0.0358 (18)	0.0334 (18)	0.051 (2)	−0.0075 (14)	−0.0088 (15)	−0.0022 (15)

C1—C2	1.383 (5)	C5—H5	0.9300
C1—C6	1.422 (6)	C6—C8	1.506 (5)
C1—C9	1.522 (5)	C7—H7	0.9300
N1—C7	1.332 (5)	O1W—H2W	0.8400
N1—C4	1.387 (5)	O1W—H1W	0.8400
N1—H1	0.8600	O2W—H3W	0.8400
Ni1—O3W	2.029 (3)	O2W—H4W	0.8400
Ni1—O4W	2.053 (3)	O3W—H5W	0.8400
Ni1—N2	2.052 (3)	O3W—H6W	0.8400
Ni1—O2W	2.069 (3)	O4W—H7W	0.8400
Ni1—O1W	2.078 (3)	O4W—H8W	0.8400
Ni1—O5W	2.099 (3)	O5W—H9W	0.8400
O1—C9	1.242 (5)	O5W—H10W	0.8400
C2—C3	1.390 (5)	O6W—H11W	0.8400
C2—H2	0.9300	O6W—H12W	0.8400
N2—C7	1.325 (5)	O7W—H14W	0.8400
N2—C3	1.398 (5)	O7W—H13W	0.8400
O2—C9	1.247 (5)	O8W—H16W	0.8400
C3—C4	1.400 (6)	O8W—H15W	0.8400
O3—C8	1.250 (5)	O9W—H18W	0.8400
C4—C5	1.384 (6)	O9W—H17W	0.8400
O4—C8	1.263 (5)	O10W—H19W	0.8400
C5—C6	1.383 (5)	O10W—H20W	0.8400
C2—C1—C6	121.3 (3)	C6—C5—H5	121.1
C2—C1—C9	117.1 (3)	C4—C5—H5	121.1
C6—C1—C9	121.5 (3)	C5—C6—C1	120.4 (4)
C7—N1—C4	107.6 (3)	C5—C6—C8	118.6 (3)
C7—N1—H1	126.2	C1—C6—C8	120.9 (3)
C4—N1—H1	126.2	N2—C7—N1	113.3 (3)
O3W—Ni1—O4W	88.73 (14)	N2—C7—H7	123.4
O3W—Ni1—N2	176.19 (13)	N1—C7—H7	123.4
O4W—Ni1—N2	87.52 (13)	O3—C8—O4	124.7 (4)
O3W—Ni1—O2W	86.14 (14)	O3—C8—C6	118.0 (4)
O4W—Ni1—O2W	92.83 (12)	O4—C8—C6	117.1 (3)
N2—Ni1—O2W	94.75 (13)	O1—C9—O2	124.9 (4)
O3W—Ni1—O1W	90.63 (14)	O1—C9—C1	117.3 (3)
O4W—Ni1—O1W	176.58 (11)	O2—C9—C1	117.7 (4)
N2—Ni1—O1W	93.07 (13)	Ni1—O1W—H2W	117.9
O2W—Ni1—O1W	90.49 (11)	Ni1—O1W—H1W	106.6
O3W—Ni1—O5W	89.34 (13)	H2W—O1W—H1W	111.6
O4W—Ni1—O5W	88.84 (13)	Ni1—O2W—H3W	119.4
N2—Ni1—O5W	89.88 (13)	Ni1—O2W—H4W	115.2
O2W—Ni1—O5W	175.15 (11)	H3W—O2W—H4W	111.6
O1W—Ni1—O5W	87.79 (12)	Ni1—O3W—H5W	122.7
C1—C2—C3	118.0 (4)	Ni1—O3W—H6W	125.1
C1—C2—H2	121.0	H5W—O3W—H6W	111.9
C3—C2—H2	121.0	Ni1—O4W—H7W	113.0
C7—N2—C3	104.9 (3)	Ni1—O4W—H8W	119.4
C7—N2—Ni1	122.5 (3)	H7W—O4W—H8W	111.4
C3—N2—Ni1	132.1 (3)	Ni1—O5W—H9W	112.7
C2—C3—N2	130.8 (4)	Ni1—O5W—H10W	119.8
C2—C3—C4	120.3 (4)	H9W—O5W—H10W	111.1
N2—C3—C4	108.9 (3)	H11W—O6W—H12W	111.6
N1—C4—C5	132.6 (4)	H14W—O7W—H13W	111.7
N1—C4—C3	105.3 (3)	H16W—O8W—H15W	111.6
C5—C4—C3	122.2 (4)	H18W—O9W—H17W	111.7
C6—C5—C4	117.8 (4)	H19W—O10W—H20W	111.4

D—H···A	D—H	H···A	D···A	D—H···A
O10W—H20W···O1W	0.84	2.00	2.836 (4)	176
O10W—H19W···O8Wi	0.84	1.88	2.703 (5)	166
O9W—H17W···O3ii	0.84	1.90	2.733 (5)	172
O9W—H18W···O10Wiii	0.84	1.91	2.720 (5)	163
O8W—H15W···O1iv	0.84	1.95	2.765 (5)	163
O8W—H16W···O2	0.84	1.96	2.775 (5)	162
O7W—H13W···O8Wv	0.84	1.93	2.754 (5)	165
O7W—H14W···O4v	0.84	1.91	2.734 (5)	169
O6W—H12W···O2Wvi	0.84	2.06	2.857 (4)	159
O6W—H11W···O4vii	0.84	1.97	2.808 (4)	174
O5W—H10W···O4viii	0.84	1.96	2.800 (4)	176
O5W—H9W···O9Wiii	0.84	1.98	2.817 (4)	173
O4W—H8W···O9Wv	0.84	1.90	2.736 (5)	173
O4W—H7W···O3ix	0.84	1.94	2.709 (4)	151
O3W—H6W···O6Wviii	0.84	1.93	2.761 (4)	172
O3W—H5W···O7Wx	0.84	1.93	2.729 (5)	159
O2W—H4W···O1v	0.84	1.80	2.620 (4)	164
O2W—H3W···O10Wiv	0.84	1.90	2.734 (5)	175
O1W—H1W···O6Wv	0.84	1.96	2.783 (5)	168
O1W—H2W···O2v	0.84	1.79	2.612 (4)	166
N1—H1···O7Wxi	0.86	1.97	2.803 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10W—H20W⋯O1W	0.84	2.00	2.836 (4)	176
O10W—H19W⋯O8Wi	0.84	1.88	2.703 (5)	166
O9W—H17W⋯O3ii	0.84	1.90	2.733 (5)	172
O9W—H18W⋯O10Wiii	0.84	1.91	2.720 (5)	163
O8W—H15W⋯O1iv	0.84	1.95	2.765 (5)	163
O8W—H16W⋯O2	0.84	1.96	2.775 (5)	162
O7W—H13W⋯O8Wv	0.84	1.93	2.754 (5)	165
O7W—H14W⋯O4v	0.84	1.91	2.734 (5)	169
O6W—H12W⋯O2Wvi	0.84	2.06	2.857 (4)	159
O6W—H11W⋯O4vii	0.84	1.97	2.808 (4)	174
O5W—H10W⋯O4viii	0.84	1.96	2.800 (4)	176
O5W—H9W⋯O9Wiii	0.84	1.98	2.817 (4)	173
O4W—H8W⋯O9Wv	0.84	1.90	2.736 (5)	173
O4W—H7W⋯O3ix	0.84	1.94	2.709 (4)	151
O3W—H6W⋯O6Wviii	0.84	1.93	2.761 (4)	172
O3W—H5W⋯O7Wx	0.84	1.93	2.729 (5)	159
O2W—H4W⋯O1v	0.84	1.80	2.620 (4)	164
O2W—H3W⋯O10Wiv	0.84	1.90	2.734 (5)	175
O1W—H1W⋯O6Wv	0.84	1.96	2.783 (5)	168
O1W—H2W⋯O2v	0.84	1.79	2.612 (4)	166
N1—H1⋯O7Wxi	0.86	1.97	2.803 (5)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) ; (xi) .