Bis[2-(1H-benzimidazol-2-yl)benzoato]copper(II) dihydrate.

In the title compound, [Cu(C(14)H(9)N(2)O(2))(2)]·2H(2)O, the Cu(II) ion lies on a centre of symmetry and is four-coordinated by two N atoms and two O atoms from two 2-(1H-benzimidazol-2-yl)benzoate ligands in a square-planar environment. The benzimidazol and benzyl rings form a dihedral angle of 42.8 (5)°. The mol-ecule contains two H-bonded carboxyl O acceptors and two H-bonded N-H donors in the benzimidazol groups, which inter-act with two symmetry-related uncoordinated water mol-ecules so that neighboring mol-ecular units are linked by (O-H)(water)⋯O(carbox-yl) hydrogen bonds with an R(2) (4)(8) graph-set motif, generating a helical chain in the a-axis direction. These chains are, in turn, inter-connected by (N-H)(benzimidazol)⋯O(water) hydrogen bonds, forming a three-dimensional supra-molecular network.

Related literature

For the structural diversity and potential applications in functional materials of metal coordination polymers based on benzimidazole derivatives, see: Aminabhavi et al. (1986 ▶); Isele et al. (2005 ▶). For similar structures, see: Che et al. (2006 ▶); Fang et al. (2006 ▶); Liu et al. (2004 ▶); Li et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Cu(C14H9N2O2)2]·2H2O

M = 574.04

Monoclinic,

a = 11.6235 (2) Å

b = 7.6920 (2) Å

c = 16.1410 (3) Å

β = 115.735 (1)°

V = 1299.99 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.89 mm−1

T = 296 K

0.23 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.821, T max = 0.871

14480 measured reflections

2974 independent reflections

1854 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.110

S = 1.00

2974 reflections

178 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037633/bg2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037633/bg2369Isup2.hkl

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

[Cu(C14H9N2O2)2]·2H2O	F(000) = 590
Mr = 574.04	Dx = 1.466 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4800 reflections
a = 11.6235 (2) Å	θ = 1.4–28.0°
b = 7.6920 (2) Å	µ = 0.89 mm−1
c = 16.1410 (3) Å	T = 296 K
β = 115.735 (1)°	Block, blue
V = 1299.99 (5) Å3	0.23 × 0.21 × 0.16 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2974 independent reflections
Radiation source: fine-focus sealed tube	1854 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scan	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −15→14
Tmin = 0.821, Tmax = 0.871	k = −9→9
14480 measured reflections	l = −20→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.7646P] where P = (Fo2 + 2Fc2)/3
2974 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 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
Cu1	0.5000	0.5000	0.5000	0.03258 (17)
C1	0.5169 (3)	0.8319 (4)	0.6049 (2)	0.0354 (7)
C2	0.4078 (3)	0.9168 (4)	0.5430 (2)	0.0439 (8)
H2	0.3519	0.8648	0.4883	0.053*
C3	0.3861 (4)	1.0813 (5)	0.5665 (3)	0.0511 (9)
H3	0.3139	1.1414	0.5265	0.061*
C4	0.4686 (4)	1.1600 (5)	0.6478 (3)	0.0582 (10)
H4	0.4508	1.2721	0.6605	0.070*
C5	0.5758 (4)	1.0775 (5)	0.7099 (3)	0.0535 (10)
H5	0.6302	1.1301	0.7649	0.064*
C6	0.5994 (3)	0.9111 (4)	0.6870 (2)	0.0400 (8)
C7	0.6757 (3)	0.6520 (4)	0.6772 (2)	0.0332 (7)
C8	0.7588 (3)	0.4981 (4)	0.7070 (2)	0.0358 (7)
C9	0.8024 (3)	0.4489 (5)	0.7992 (2)	0.0504 (9)
H9	0.7779	0.5126	0.8378	0.060*
C10	0.8814 (4)	0.3068 (5)	0.8332 (3)	0.0632 (11)
H10	0.9096	0.2750	0.8945	0.076*
C11	0.9187 (3)	0.2119 (5)	0.7768 (3)	0.0604 (11)
H11	0.9700	0.1141	0.7994	0.072*
C12	0.8798 (3)	0.2620 (4)	0.6868 (2)	0.0502 (9)
H12	0.9075	0.1995	0.6495	0.060*
C13	0.7996 (3)	0.4051 (4)	0.6504 (2)	0.0367 (7)
C14	0.7735 (3)	0.4580 (4)	0.5535 (2)	0.0386 (8)
N1	0.5679 (2)	0.6681 (3)	0.60034 (16)	0.0327 (6)
N2	0.6971 (2)	0.7946 (3)	0.73035 (17)	0.0413 (7)
H2A	0.7614	0.8103	0.7828	0.050*
O1	0.66231 (18)	0.4956 (3)	0.49508 (13)	0.0392 (5)
O2	0.8661 (2)	0.4584 (4)	0.53508 (16)	0.0636 (8)
O1W	0.8855 (2)	0.8417 (3)	0.90275 (15)	0.0624 (7)
H1W	0.8680	0.8979	0.9406	0.094*
H2W	0.9618	0.8657	0.9144	0.094*

	U11	U22	U33	U12	U13	U23
Cu1	0.0257 (3)	0.0338 (3)	0.0323 (3)	0.0030 (3)	0.0070 (2)	−0.0034 (3)
C1	0.0397 (19)	0.0320 (17)	0.0387 (18)	−0.0002 (14)	0.0210 (15)	−0.0016 (15)
C2	0.042 (2)	0.0385 (19)	0.049 (2)	0.0043 (16)	0.0178 (17)	0.0018 (17)
C3	0.054 (2)	0.041 (2)	0.066 (3)	0.0104 (19)	0.034 (2)	0.0083 (19)
C4	0.074 (3)	0.033 (2)	0.087 (3)	0.0080 (19)	0.053 (3)	−0.003 (2)
C5	0.064 (3)	0.042 (2)	0.061 (2)	−0.0088 (19)	0.032 (2)	−0.0177 (19)
C6	0.042 (2)	0.0360 (18)	0.046 (2)	−0.0016 (16)	0.0223 (17)	−0.0025 (16)
C7	0.0321 (17)	0.0363 (18)	0.0308 (16)	−0.0041 (14)	0.0132 (14)	−0.0034 (14)
C8	0.0265 (15)	0.0371 (16)	0.0371 (17)	−0.0048 (16)	0.0076 (13)	0.0013 (16)
C9	0.050 (2)	0.056 (2)	0.041 (2)	0.0050 (17)	0.0153 (17)	0.0057 (16)
C10	0.059 (3)	0.073 (3)	0.047 (2)	0.009 (2)	0.014 (2)	0.022 (2)
C11	0.051 (2)	0.059 (2)	0.066 (3)	0.023 (2)	0.021 (2)	0.029 (2)
C12	0.043 (2)	0.051 (2)	0.058 (2)	0.0089 (17)	0.0228 (18)	0.0113 (18)
C13	0.0288 (17)	0.0374 (18)	0.0396 (18)	0.0014 (14)	0.0109 (14)	0.0048 (15)
C14	0.0335 (19)	0.038 (2)	0.0420 (19)	0.0006 (14)	0.0142 (16)	0.0020 (14)
N1	0.0292 (14)	0.0314 (14)	0.0326 (14)	0.0024 (11)	0.0089 (11)	−0.0040 (11)
N2	0.0385 (16)	0.0449 (17)	0.0335 (14)	−0.0063 (13)	0.0090 (12)	−0.0094 (13)
O1	0.0296 (12)	0.0483 (13)	0.0362 (12)	0.0045 (11)	0.0111 (9)	0.0010 (11)
O2	0.0334 (14)	0.109 (2)	0.0530 (15)	0.0133 (14)	0.0232 (12)	0.0240 (14)
O1W	0.0453 (15)	0.0879 (19)	0.0496 (15)	−0.0167 (14)	0.0165 (12)	−0.0258 (14)

Cu1—O1i	1.9227 (19)	C7—C8	1.470 (4)
Cu1—O1	1.9227 (19)	C8—C13	1.396 (4)
Cu1—N1	1.951 (2)	C8—C9	1.400 (4)
Cu1—N1i	1.951 (2)	C9—C10	1.379 (5)
C1—C2	1.390 (4)	C9—H9	0.9300
C1—C6	1.395 (4)	C10—C11	1.376 (5)
C1—N1	1.407 (4)	C10—H10	0.9300
C2—C3	1.374 (5)	C11—C12	1.376 (5)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.384 (5)	C12—C13	1.396 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.370 (5)	C13—C14	1.513 (4)
C4—H4	0.9300	C14—O2	1.235 (4)
C5—C6	1.392 (5)	C14—O1	1.259 (3)
C5—H5	0.9300	N2—H2A	0.8600
C6—N2	1.376 (4)	O1W—H1W	0.8415
C7—N1	1.333 (3)	O1W—H2W	0.8432
C7—N2	1.347 (3)
O1i—Cu1—O1	180.0	C13—C8—C7	124.1 (3)
O1i—Cu1—N1	90.25 (9)	C9—C8—C7	116.6 (3)
O1—Cu1—N1	89.75 (9)	C10—C9—C8	120.6 (3)
O1i—Cu1—N1i	89.75 (9)	C10—C9—H9	119.7
O1—Cu1—N1i	90.25 (9)	C8—C9—H9	119.7
N1—Cu1—N1i	180.0	C11—C10—C9	120.2 (3)
C2—C1—C6	120.9 (3)	C11—C10—H10	119.9
C2—C1—N1	131.1 (3)	C9—C10—H10	119.9
C6—C1—N1	108.0 (3)	C12—C11—C10	119.8 (3)
C3—C2—C1	117.0 (3)	C12—C11—H11	120.1
C3—C2—H2	121.5	C10—C11—H11	120.1
C1—C2—H2	121.5	C11—C12—C13	121.3 (3)
C2—C3—C4	122.0 (3)	C11—C12—H12	119.4
C2—C3—H3	119.0	C13—C12—H12	119.4
C4—C3—H3	119.0	C8—C13—C12	118.9 (3)
C5—C4—C3	121.8 (3)	C8—C13—C14	124.4 (3)
C5—C4—H4	119.1	C12—C13—C14	116.4 (3)
C3—C4—H4	119.1	O2—C14—O1	122.5 (3)
C4—C5—C6	116.9 (3)	O2—C14—C13	116.4 (3)
C4—C5—H5	121.5	O1—C14—C13	121.1 (3)
C6—C5—H5	121.5	C7—N1—C1	106.4 (2)
N2—C6—C5	132.7 (3)	C7—N1—Cu1	126.1 (2)
N2—C6—C1	105.9 (3)	C1—N1—Cu1	127.5 (2)
C5—C6—C1	121.4 (3)	C7—N2—C6	108.8 (3)
N1—C7—N2	110.9 (3)	C7—N2—H2A	125.6
N1—C7—C8	126.7 (3)	C6—N2—H2A	125.6
N2—C7—C8	122.3 (3)	C14—O1—Cu1	132.8 (2)
C13—C8—C9	119.2 (3)	H1W—O1W—H2W	106.7

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1W	0.86	1.86	2.716 (3)	173
O1W—H1W···O2ii	0.84	1.89	2.720 (3)	167
O1W—H2W···O2iii	0.84	1.94	2.763 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1W	0.86	1.86	2.716 (3)	173
O1W—H1W⋯O2i	0.84	1.89	2.720 (3)	167
O1W—H2W⋯O2ii	0.84	1.94	2.763 (3)	165

Symmetry codes: (i) ; (ii) .