catena-Poly[[dichloridocopper(II)]-μ-4,4'-bis-(benzimidazol-1-yl)biphen-yl].

In the title compound, [CuCl(2)(C(26)H(18)N(4))](n), the Cu(II) ion is four-coordinated by two N atoms from two 4,4'-bis-(benzo-imidazol-1-yl)biphenyl ligands and two chloride anions, in a slightly distorted tetra-hedral environment. The biphenyl ligand acts as a linear bidentate ligand, connecting the metal atoms into an infinite chain parallel to [101]. In the biphenyl ligand, the two benzene rings make a dihedral angle of 33.19 (7)°.

Related literature

For background to benzimidazole-based ligands in crystal engineering, see: Jin et al. (2006 ▶); Li et al. (2009 ▶); Su et al. (2003 ▶).

Experimental

Crystal data

[CuCl2(C26H18N4)]

M = 520.88

Monoclinic,

a = 12.599 (4) Å

b = 15.280 (4) Å

c = 11.233 (3) Å

β = 91.936 (4)°

V = 2161.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.28 mm−1

T = 293 K

0.04 × 0.03 × 0.02 mm

Data collection

Rigaku Mercury CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.955, T max = 0.975

6675 measured reflections

1903 independent reflections

1761 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.066

S = 1.06

1903 reflections

151 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011421/fj2406sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011421/fj2406Isup2.hkl

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

[CuCl2(C26H18N4)]	F(000) = 1060
Mr = 520.88	Dx = 1.601 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2903 reflections
a = 12.599 (4) Å	θ = 2.1–27.9°
b = 15.280 (4) Å	µ = 1.28 mm−1
c = 11.233 (3) Å	T = 293 K
β = 91.936 (4)°	Block, brown
V = 2161.3 (10) Å3	0.04 × 0.03 × 0.02 mm
Z = 4

Rigaku Mercury CCD area-detector diffractometer	1903 independent reflections
Radiation source: fine-focus sealed tube	1761 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 9 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −18→18
Tmin = 0.955, Tmax = 0.975	l = −13→13
6675 measured reflections

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0296P)2 + 3.937P] where P = (Fo2 + 2Fc2)/3
1903 reflections	(Δ/σ)max = 0.002
151 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.27 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	1.0000	1.09184 (2)	0.7500	0.01275 (12)
Cl1	0.98903 (4)	1.18252 (3)	0.59365 (5)	0.02221 (15)
N1	0.89293 (14)	1.01051 (11)	0.81368 (14)	0.0136 (4)
N2	0.75910 (13)	0.96997 (11)	0.92601 (15)	0.0128 (4)
C1	0.83320 (16)	1.03097 (13)	0.90401 (18)	0.0138 (4)
H1	0.8414	1.0822	0.9480	0.017*
C2	0.85403 (16)	0.92994 (13)	0.77153 (18)	0.0121 (4)
C3	0.88572 (16)	0.87841 (13)	0.67670 (17)	0.0133 (4)
H3	0.9422	0.8949	0.6304	0.016*
C4	0.83018 (17)	0.80212 (13)	0.65424 (19)	0.0158 (4)
H4	0.8493	0.7666	0.5913	0.019*
C5	0.74523 (17)	0.77700 (13)	0.72469 (19)	0.0168 (5)
H5	0.7089	0.7255	0.7064	0.020*
C6	0.71401 (17)	0.82661 (13)	0.82038 (19)	0.0142 (4)
H6	0.6584	0.8095	0.8676	0.017*
C7	0.77056 (16)	0.90357 (13)	0.84203 (17)	0.0125 (4)
C8	0.68519 (16)	0.97360 (13)	1.02045 (18)	0.0132 (4)
C9	0.66932 (17)	0.89992 (14)	1.08940 (19)	0.0177 (5)
H9	0.7071	0.8488	1.0756	0.021*
C10	0.59681 (17)	0.90309 (14)	1.17892 (19)	0.0177 (5)
H10	0.5857	0.8533	1.2245	0.021*
C11	0.53980 (16)	0.97924 (13)	1.20262 (17)	0.0129 (4)
C12	0.55967 (16)	1.05353 (13)	1.13412 (18)	0.0129 (4)
H12	0.5247	1.1056	1.1502	0.015*
C13	0.63069 (16)	1.05066 (13)	1.04257 (18)	0.0137 (4)
H13	0.6418	1.1000	0.9962	0.016*

	U11	U22	U33	U12	U13	U23
Cu1	0.0123 (2)	0.01272 (19)	0.01364 (19)	0.000	0.00700 (14)	0.000
Cl1	0.0252 (3)	0.0219 (3)	0.0202 (3)	0.0108 (2)	0.0105 (2)	0.0070 (2)
N1	0.0132 (9)	0.0158 (9)	0.0121 (9)	−0.0018 (7)	0.0043 (7)	−0.0008 (7)
N2	0.0121 (9)	0.0151 (8)	0.0114 (8)	−0.0016 (7)	0.0052 (7)	0.0000 (7)
C1	0.0118 (11)	0.0166 (10)	0.0131 (10)	−0.0021 (8)	0.0037 (8)	−0.0004 (8)
C2	0.0110 (10)	0.0138 (10)	0.0114 (10)	−0.0011 (8)	0.0011 (8)	0.0014 (8)
C3	0.0119 (11)	0.0172 (10)	0.0108 (10)	0.0016 (8)	0.0022 (8)	0.0018 (8)
C4	0.0178 (11)	0.0155 (10)	0.0141 (10)	0.0043 (8)	0.0010 (9)	−0.0024 (8)
C5	0.0164 (11)	0.0115 (10)	0.0226 (11)	−0.0030 (8)	0.0003 (9)	0.0013 (9)
C6	0.0112 (10)	0.0140 (10)	0.0177 (11)	−0.0012 (8)	0.0035 (8)	0.0036 (8)
C7	0.0106 (10)	0.0155 (10)	0.0114 (10)	0.0011 (8)	0.0031 (8)	0.0018 (8)
C8	0.0100 (10)	0.0198 (11)	0.0099 (10)	−0.0020 (8)	0.0033 (8)	−0.0003 (8)
C9	0.0183 (12)	0.0173 (11)	0.0181 (11)	0.0054 (9)	0.0082 (9)	0.0019 (9)
C10	0.0197 (12)	0.0180 (11)	0.0160 (11)	0.0011 (9)	0.0082 (9)	0.0055 (9)
C11	0.0101 (11)	0.0175 (11)	0.0112 (10)	−0.0003 (8)	0.0018 (8)	−0.0009 (8)
C12	0.0103 (10)	0.0141 (10)	0.0142 (10)	−0.0003 (8)	0.0015 (8)	−0.0028 (8)
C13	0.0146 (11)	0.0135 (10)	0.0130 (10)	−0.0045 (8)	0.0018 (8)	0.0016 (8)

Cu1—N1i	1.9851 (17)	C5—C6	1.383 (3)
Cu1—N1	1.9851 (17)	C5—H5	0.9300
Cu1—Cl1i	2.2378 (7)	C6—C7	1.392 (3)
Cu1—Cl1	2.2378 (7)	C6—H6	0.9300
N1—C1	1.321 (3)	C8—C9	1.385 (3)
N1—C2	1.402 (3)	C8—C13	1.390 (3)
N2—C1	1.348 (3)	C9—C10	1.382 (3)
N2—C7	1.396 (3)	C9—H9	0.9300
N2—C8	1.436 (3)	C10—C11	1.398 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.394 (3)	C11—C12	1.399 (3)
C2—C7	1.397 (3)	C11—C11ii	1.487 (4)
C3—C4	1.379 (3)	C12—C13	1.387 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.406 (3)	C13—H13	0.9300
C4—H4	0.9300
N1i—Cu1—N1	102.49 (10)	C4—C5—H5	119.0
N1i—Cu1—Cl1i	130.22 (5)	C5—C6—C7	116.19 (19)
N1—Cu1—Cl1i	97.44 (5)	C5—C6—H6	121.9
N1i—Cu1—Cl1	97.44 (5)	C7—C6—H6	121.9
N1—Cu1—Cl1	130.22 (5)	C6—C7—N2	131.90 (19)
Cl1i—Cu1—Cl1	103.48 (4)	C6—C7—C2	122.36 (19)
C1—N1—C2	105.40 (17)	N2—C7—C2	105.69 (17)
C1—N1—Cu1	122.71 (14)	C9—C8—C13	120.48 (19)
C2—N1—Cu1	131.47 (14)	C9—C8—N2	119.42 (18)
C1—N2—C7	106.89 (17)	C13—C8—N2	120.10 (18)
C1—N2—C8	125.39 (17)	C10—C9—C8	119.3 (2)
C7—N2—C8	127.71 (17)	C10—C9—H9	120.3
N1—C1—N2	113.16 (18)	C8—C9—H9	120.3
N1—C1—H1	123.4	C9—C10—C11	121.6 (2)
N2—C1—H1	123.4	C9—C10—H10	119.2
C3—C2—C7	120.72 (18)	C11—C10—H10	119.2
C3—C2—N1	130.42 (19)	C10—C11—C12	117.91 (19)
C7—C2—N1	108.85 (18)	C10—C11—C11ii	119.99 (13)
C4—C3—C2	117.44 (19)	C12—C11—C11ii	122.10 (13)
C4—C3—H3	121.3	C13—C12—C11	120.95 (19)
C2—C3—H3	121.3	C13—C12—H12	119.5
C3—C4—C5	121.28 (19)	C11—C12—H12	119.5
C3—C4—H4	119.4	C12—C13—C8	119.64 (19)
C5—C4—H4	119.4	C12—C13—H13	120.2
C6—C5—C4	121.99 (19)	C8—C13—H13	120.2
C6—C5—H5	119.0
N1i—Cu1—N1—C1	151.17 (19)	C8—N2—C7—C6	3.6 (3)
Cl1i—Cu1—N1—C1	17.06 (16)	C1—N2—C7—C2	−0.2 (2)
Cl1—Cu1—N1—C1	−97.67 (16)	C8—N2—C7—C2	−178.85 (18)
N1i—Cu1—N1—C2	−37.46 (15)	C3—C2—C7—C6	−1.3 (3)
Cl1i—Cu1—N1—C2	−171.56 (17)	N1—C2—C7—C6	178.54 (18)
Cl1—Cu1—N1—C2	73.71 (19)	C3—C2—C7—N2	−179.11 (18)
C2—N1—C1—N2	0.9 (2)	N1—C2—C7—N2	0.7 (2)
Cu1—N1—C1—N2	174.20 (13)	C1—N2—C8—C9	−134.1 (2)
C7—N2—C1—N1	−0.4 (2)	C7—N2—C8—C9	44.3 (3)
C8—N2—C1—N1	178.25 (18)	C1—N2—C8—C13	45.5 (3)
C1—N1—C2—C3	178.8 (2)	C7—N2—C8—C13	−136.1 (2)
Cu1—N1—C2—C3	6.4 (3)	C13—C8—C9—C10	1.5 (3)
C1—N1—C2—C7	−1.0 (2)	N2—C8—C9—C10	−178.90 (19)
Cu1—N1—C2—C7	−173.47 (14)	C8—C9—C10—C11	−0.7 (3)
C7—C2—C3—C4	1.4 (3)	C9—C10—C11—C12	−1.2 (3)
N1—C2—C3—C4	−178.4 (2)	C9—C10—C11—C11ii	178.2 (2)
C2—C3—C4—C5	−0.4 (3)	C10—C11—C12—C13	2.4 (3)
C3—C4—C5—C6	−0.8 (3)	C11ii—C11—C12—C13	−176.9 (2)
C4—C5—C6—C7	0.9 (3)	C11—C12—C13—C8	−1.8 (3)
C5—C6—C7—N2	177.3 (2)	C9—C8—C13—C12	−0.2 (3)
C5—C6—C7—C2	0.2 (3)	N2—C8—C13—C12	−179.86 (18)
C1—N2—C7—C6	−177.7 (2)