Bis[μ-3-(1H-benzimidazol-2-yl)benzoato]dicopper(I).

The dimeric title complex, [Cu(2)(C(14)H(9)N(2)O(2))(2)], resides on a center of symmetry. In the crystal, the mol-ecules are packed via π-π stacking inter-actions alternating between imidazole and benzene rings [mean inter-planar distances = 3.754 (3) and 3.624 (3) Å]. An inter-molecular N-H⋯O hydrogen bond links the dimers together. The two-coordinate Cu(I) atom displays an O-Cu-N bond angle of 176.3 (2)°. The Cu⋯Cu distance within the dimer is 5.100 (2) Å.

Related literature

For background to complexes of benzimidazole with n class="Chemical">copper(I), see: Ruettimann et al. (1992 ▶).

Experimental

Crystal data

[Cu2(C14n class="Species">H9N2O2)2]

M = 601.54

Monoclinic,

a = 4.875 (2) Å

b = 13.417 (7) Å

c = 18.130 (9) Å

β = 103.643 (12)°

V = 1152.4 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.89 mm−1

T = 296 K

0.52 × 0.44 × 0.40 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.387, T max = 0.473

7794 measured reflections

2013 independent reflections

1083 reflections with I > 2σ(I)

R int = 0.107

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.148

S = 1.01

2013 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046040/om2365sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046040/om2365Isup2.hkl

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

[Cu2(C14H9N2O2)2]	F(000) = 608
Mr = 601.54	Dx = 1.734 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1146 reflections
a = 4.875 (2) Å	θ = 2.3–21.7°
b = 13.417 (7) Å	µ = 1.89 mm−1
c = 18.130 (9) Å	T = 296 K
β = 103.643 (12)°	Block, brown
V = 1152.4 (10) Å3	0.52 × 0.44 × 0.40 mm
Z = 2

Bruker SMART APEXII diffractometer	2013 independent reflections
Radiation source: fine-focus sealed tube	1083 reflections with I > 2σ(I)
graphite	Rint = 0.107
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −5→4
Tmin = 0.387, Tmax = 0.473	k = −15→15
7794 measured reflections	l = −21→21

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) = 0.148	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0617P)2 + 0.5546P] where P = (Fo2 + 2Fc2)/3
2013 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.62 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
Cu1	0.09380 (19)	0.62278 (7)	0.49047 (4)	0.0455 (3)
O1	0.0431 (11)	0.6329 (4)	0.3136 (3)	0.0546 (13)
O2	0.2212 (11)	0.5488 (4)	0.4211 (2)	0.0528 (14)
N1	1.0395 (10)	0.2257 (4)	0.3273 (3)	0.0336 (13)
H1	0.9989	0.2078	0.2804	0.040*
N2	1.0206 (11)	0.3061 (4)	0.4335 (3)	0.0340 (13)
C1	1.4326 (14)	0.2163 (5)	0.5182 (4)	0.0433 (18)
H1A	1.4275	0.2497	0.5628	0.052*
C2	1.6298 (14)	0.1429 (6)	0.5170 (4)	0.051 (2)
H2	1.7583	0.1263	0.5620	0.061*
C3	1.6418 (15)	0.0926 (5)	0.4499 (5)	0.053 (2)
H3	1.7786	0.0438	0.4516	0.064*
C4	1.4583 (14)	0.1134 (5)	0.3825 (4)	0.0433 (18)
H4	1.4664	0.0801	0.3381	0.052*
C5	1.2557 (13)	0.1879 (5)	0.3836 (4)	0.0363 (16)
C6	1.2412 (13)	0.2388 (5)	0.4501 (4)	0.0343 (16)
C7	0.9009 (13)	0.2964 (5)	0.3587 (3)	0.0339 (16)
C8	0.6567 (13)	0.3523 (4)	0.3147 (3)	0.0317 (16)
C9	0.5412 (14)	0.3314 (5)	0.2385 (4)	0.0407 (17)
H9	0.6192	0.2812	0.2145	0.049*
C10	0.3124 (14)	0.3844 (5)	0.1981 (4)	0.0472 (19)
H10	0.2345	0.3689	0.1475	0.057*
C11	0.1979 (14)	0.4609 (5)	0.2330 (4)	0.0419 (18)
H11	0.0468	0.4978	0.2053	0.050*
C12	0.3074 (13)	0.4824 (4)	0.3086 (3)	0.0311 (15)
C13	0.5339 (13)	0.4285 (5)	0.3486 (4)	0.0347 (16)
H13	0.6073	0.4432	0.3996	0.042*
C14	0.1782 (14)	0.5627 (5)	0.3490 (4)	0.0378 (17)

	U11	U22	U33	U12	U13	U23
Cu1	0.0639 (6)	0.0446 (6)	0.0288 (5)	0.0096 (5)	0.0128 (4)	−0.0037 (4)
O1	0.075 (4)	0.049 (3)	0.042 (3)	0.021 (3)	0.018 (3)	0.008 (2)
O2	0.083 (4)	0.050 (3)	0.026 (3)	0.022 (3)	0.014 (2)	0.002 (2)
N1	0.035 (3)	0.036 (3)	0.031 (3)	0.002 (3)	0.009 (3)	−0.002 (3)
N2	0.045 (3)	0.032 (3)	0.027 (3)	0.000 (3)	0.012 (3)	0.000 (2)
C1	0.050 (4)	0.042 (4)	0.039 (4)	−0.008 (4)	0.012 (3)	0.005 (3)
C2	0.039 (4)	0.053 (5)	0.054 (5)	−0.005 (4)	−0.002 (4)	0.017 (4)
C3	0.046 (5)	0.039 (5)	0.077 (6)	0.009 (4)	0.019 (4)	0.008 (4)
C4	0.048 (4)	0.038 (4)	0.047 (4)	−0.002 (4)	0.018 (3)	−0.001 (4)
C5	0.034 (4)	0.035 (4)	0.043 (4)	−0.002 (3)	0.018 (3)	0.004 (3)
C6	0.032 (4)	0.040 (4)	0.031 (4)	0.003 (3)	0.009 (3)	0.003 (3)
C7	0.039 (4)	0.033 (4)	0.031 (4)	−0.007 (3)	0.012 (3)	0.005 (3)
C8	0.035 (4)	0.029 (4)	0.032 (4)	−0.003 (3)	0.012 (3)	0.004 (3)
C9	0.046 (4)	0.046 (4)	0.031 (4)	0.006 (4)	0.009 (3)	−0.009 (3)
C10	0.054 (5)	0.060 (5)	0.026 (4)	0.006 (4)	0.009 (3)	−0.013 (4)
C11	0.045 (4)	0.048 (5)	0.032 (4)	0.002 (4)	0.009 (3)	0.003 (3)
C12	0.039 (4)	0.031 (4)	0.026 (3)	0.001 (3)	0.013 (3)	−0.001 (3)
C13	0.044 (4)	0.031 (4)	0.029 (4)	−0.002 (3)	0.010 (3)	−0.004 (3)
C14	0.048 (4)	0.036 (4)	0.031 (4)	−0.001 (4)	0.011 (3)	0.001 (3)

Cu1—O2	1.823 (5)	C3—H3	0.9300
Cu1—N2i	1.867 (5)	C4—C5	1.408 (9)
O1—C14	1.239 (8)	C4—H4	0.9300
O2—C14	1.287 (7)	C5—C6	1.402 (9)
N1—C7	1.366 (8)	C7—C8	1.472 (8)
N1—C5	1.379 (8)	C8—C9	1.393 (9)
N1—H1	0.8600	C8—C13	1.399 (9)
N2—C7	1.349 (8)	C9—C10	1.378 (9)
N2—C6	1.382 (8)	C9—H9	0.9300
N2—Cu1i	1.867 (5)	C10—C11	1.391 (9)
C1—C2	1.380 (9)	C10—H10	0.9300
C1—C6	1.394 (9)	C11—C12	1.378 (8)
C1—H1A	0.9300	C11—H11	0.9300
C2—C3	1.405 (11)	C12—C13	1.375 (8)
C2—H2	0.9300	C12—C14	1.520 (9)
C3—C4	1.363 (10)	C13—H13	0.9300
O2—Cu1—N2i	176.3 (2)	C1—C6—C5	119.8 (6)
C14—O2—Cu1	128.4 (4)	N2—C7—N1	110.3 (5)
C7—N1—C5	108.3 (5)	N2—C7—C8	126.8 (6)
C7—N1—H1	125.9	N1—C7—C8	122.9 (5)
C5—N1—H1	125.9	C9—C8—C13	117.9 (6)
C7—N2—C6	106.6 (5)	C9—C8—C7	121.5 (6)
C7—N2—Cu1i	131.1 (5)	C13—C8—C7	120.6 (6)
C6—N2—Cu1i	121.7 (4)	C10—C9—C8	120.7 (6)
C2—C1—C6	117.7 (7)	C10—C9—H9	119.7
C2—C1—H1A	121.2	C8—C9—H9	119.7
C6—C1—H1A	121.2	C9—C10—C11	120.1 (6)
C1—C2—C3	121.8 (7)	C9—C10—H10	120.0
C1—C2—H2	119.1	C11—C10—H10	120.0
C3—C2—H2	119.1	C12—C11—C10	120.2 (6)
C4—C3—C2	121.7 (7)	C12—C11—H11	119.9
C4—C3—H3	119.1	C10—C11—H11	119.9
C2—C3—H3	119.1	C13—C12—C11	119.3 (6)
C3—C4—C5	116.6 (7)	C13—C12—C14	119.4 (5)
C3—C4—H4	121.7	C11—C12—C14	121.3 (6)
C5—C4—H4	121.7	C12—C13—C8	121.8 (6)
N1—C5—C6	105.8 (6)	C12—C13—H13	119.1
N1—C5—C4	131.8 (6)	C8—C13—H13	119.1
C6—C5—C4	122.4 (6)	O1—C14—O2	125.2 (6)
N2—C6—C1	131.2 (6)	O1—C14—C12	121.2 (6)
N2—C6—C5	109.0 (5)	O2—C14—C12	113.6 (6)
N2i—Cu1—O2—C14	−169 (3)	C5—N1—C7—N2	0.2 (7)
C6—C1—C2—C3	0.6 (10)	C5—N1—C7—C8	−179.8 (5)
C1—C2—C3—C4	−0.3 (11)	N2—C7—C8—C9	−176.0 (6)
C2—C3—C4—C5	−0.1 (10)	N1—C7—C8—C9	4.1 (9)
C7—N1—C5—C6	0.0 (7)	N2—C7—C8—C13	4.1 (10)
C7—N1—C5—C4	179.0 (7)	N1—C7—C8—C13	−175.8 (6)
C3—C4—C5—N1	−178.7 (7)	C13—C8—C9—C10	−0.2 (10)
C3—C4—C5—C6	0.1 (10)	C7—C8—C9—C10	180.0 (6)
C7—N2—C6—C1	−179.1 (7)	C8—C9—C10—C11	1.3 (11)
Cu1i—N2—C6—C1	−6.9 (10)	C9—C10—C11—C12	−1.8 (10)
C7—N2—C6—C5	0.4 (7)	C10—C11—C12—C13	1.1 (10)
Cu1i—N2—C6—C5	172.5 (4)	C10—C11—C12—C14	−177.3 (6)
C2—C1—C6—N2	178.8 (6)	C11—C12—C13—C8	0.0 (10)
C2—C1—C6—C5	−0.6 (10)	C14—C12—C13—C8	178.5 (6)
N1—C5—C6—N2	−0.2 (7)	C9—C8—C13—C12	−0.5 (9)
C4—C5—C6—N2	−179.3 (5)	C7—C8—C13—C12	179.4 (6)
N1—C5—C6—C1	179.3 (6)	Cu1—O2—C14—O1	1.9 (11)
C4—C5—C6—C1	0.2 (10)	Cu1—O2—C14—C12	−177.3 (4)
C6—N2—C7—N1	−0.4 (7)	C13—C12—C14—O1	156.2 (6)
Cu1i—N2—C7—N1	−171.5 (4)	C11—C12—C14—O1	−25.4 (10)
C6—N2—C7—C8	179.7 (6)	C13—C12—C14—O2	−24.5 (9)
Cu1i—N2—C7—C8	8.6 (10)	C11—C12—C14—O2	153.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.86	1.95	2.783 (7)	164

Cu1—O2	1.823 (5)
Cu1—N2i

O2—Cu1—N2i

176.3 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ii	0.86	1.95	2.783 (7)	164

Symmetry code: (ii) .