Di-μ-chlorido-bis-[(2,2'-bibenzimidazole)chloridocadmium(II)].

The title binuclear complex, [Cd(2)Cl(4)(C(14)H(10)N(4))(2)], was synthesized by the hydro-thermal reaction of CdCl(2) and the ligand 2,2'-bibenzimidazole. The mol-ecule lies on an inversion center and the metal center displays a strongly distorted trigonal-bipyramidal geometry. The Cd(II) ions are coordinated by two N atoms from the organic ligand, and by one terminal and two bridging chloride anions. The crystal structure involves inter-molecular N-H⋯Cl hydrogen bonds, resulting in a one-dimensional supra-molecular structure.

Related literature

For the synthesis of 2,2′-bibenzimidazole, see: Fieselmann et al. (1978 ▶). For general properties of CdII-based complex polymers, see: Meng et al. (2004 ▶).

Experimental

Crystal data

[Cd2Cl4(C14H10N4)2]

M = 835.12

Monoclinic,

a = 11.824 (2) Å

b = 10.784 (2) Å

c = 22.828 (5) Å

β = 91.10 (3)°

V = 2910.1 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.86 mm−1

T = 293 (2) K

0.17 × 0.16 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: none

14677 measured reflections

3337 independent reflections

2840 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.060

S = 1.14

3337 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040968/bh2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040968/bh2211Isup2.hkl

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

[Cd2Cl4(C14H10N4)2]	F(000) = 1632
Mr = 835.12	Dx = 1.906 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 13595 reflections
a = 11.824 (2) Å	θ = 3.1–27.5°
b = 10.784 (2) Å	µ = 1.86 mm−1
c = 22.828 (5) Å	T = 293 K
β = 91.10 (3)°	Prism, yellow
V = 2910.1 (10) Å3	0.17 × 0.16 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	2840 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −15→15
14677 measured reflections	k = −14→14
3337 independent reflections	l = −29→29

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0213P)2 + 2.9529P] where P = (Fo2 + 2Fc2)/3
3337 reflections	(Δ/σ)max = 0.002
190 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.7642 (2)	0.8420 (3)	0.65287 (12)	0.0352 (6)
C2	0.8455 (3)	0.8628 (3)	0.69666 (14)	0.0488 (8)
H2	0.9096	0.9102	0.6896	0.059*
C3	0.8279 (3)	0.8110 (3)	0.75062 (15)	0.0567 (9)
H3	0.8804	0.8252	0.7807	0.068*
C4	0.7338 (3)	0.7380 (3)	0.76151 (14)	0.0569 (9)
H4	0.7252	0.7037	0.7985	0.068*
C5	0.6533 (3)	0.7156 (3)	0.71877 (13)	0.0523 (9)
H5	0.5909	0.6658	0.7259	0.063*
C6	0.6688 (2)	0.7699 (3)	0.66449 (12)	0.0370 (6)
C7	0.6614 (2)	0.8380 (2)	0.57409 (11)	0.0314 (6)
C8	0.6263 (2)	0.8657 (2)	0.51432 (11)	0.0314 (6)
C9	0.5301 (2)	0.8803 (2)	0.43105 (11)	0.0319 (6)
C10	0.4514 (2)	0.8770 (3)	0.38526 (13)	0.0409 (7)
H10	0.3817	0.8381	0.3889	0.049*
C11	0.4822 (3)	0.9342 (3)	0.33429 (13)	0.0450 (7)
H11	0.4318	0.9343	0.3025	0.054*
C12	0.5875 (3)	0.9926 (3)	0.32871 (13)	0.0441 (7)
H12	0.6050	1.0302	0.2934	0.053*
C13	0.6652 (2)	0.9957 (2)	0.37397 (12)	0.0378 (6)
H13	0.7349	1.0343	0.3700	0.045*
C14	0.6356 (2)	0.9386 (2)	0.42626 (11)	0.0306 (6)
Cd1	0.851704 (16)	1.006362 (18)	0.527622 (9)	0.03487 (7)
Cl1	1.04814 (6)	0.95042 (8)	0.57022 (3)	0.04315 (18)
Cl2	0.84050 (6)	1.21444 (7)	0.57132 (3)	0.04270 (18)
N1	0.75762 (18)	0.8824 (2)	0.59515 (10)	0.0343 (5)
N2	0.60522 (19)	0.7697 (2)	0.61309 (9)	0.0386 (6)
H15	0.5416	0.7327	0.6072	0.046*
N3	0.52742 (18)	0.8349 (2)	0.48775 (9)	0.0347 (5)
H16	0.4728	0.7946	0.5032	0.042*
N4	0.69432 (18)	0.9280 (2)	0.47931 (9)	0.0324 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0327 (15)	0.0355 (15)	0.0373 (15)	0.0013 (11)	0.0013 (12)	0.0007 (12)
C2	0.0377 (17)	0.058 (2)	0.0510 (19)	−0.0033 (15)	−0.0065 (15)	0.0030 (16)
C3	0.051 (2)	0.071 (2)	0.047 (2)	0.0076 (18)	−0.0105 (16)	−0.0022 (18)
C4	0.058 (2)	0.077 (3)	0.0352 (18)	0.0122 (19)	0.0038 (16)	0.0087 (17)
C5	0.0448 (19)	0.067 (2)	0.0455 (19)	−0.0043 (16)	0.0112 (15)	0.0063 (16)
C6	0.0329 (15)	0.0432 (17)	0.0353 (15)	0.0006 (12)	0.0052 (12)	−0.0024 (13)
C7	0.0283 (14)	0.0314 (14)	0.0348 (14)	−0.0073 (11)	0.0049 (11)	−0.0026 (11)
C8	0.0276 (14)	0.0320 (14)	0.0348 (14)	−0.0081 (11)	0.0037 (11)	−0.0045 (11)
C9	0.0307 (14)	0.0312 (14)	0.0338 (14)	−0.0053 (11)	0.0019 (11)	−0.0052 (11)
C10	0.0329 (15)	0.0450 (17)	0.0446 (17)	−0.0079 (13)	−0.0029 (13)	−0.0052 (14)
C11	0.0461 (18)	0.0484 (18)	0.0400 (17)	−0.0064 (14)	−0.0103 (14)	−0.0030 (14)
C12	0.0552 (19)	0.0410 (17)	0.0363 (15)	−0.0103 (14)	0.0022 (14)	0.0006 (13)
C13	0.0383 (15)	0.0364 (15)	0.0389 (15)	−0.0119 (12)	0.0071 (12)	−0.0028 (13)
C14	0.0302 (14)	0.0282 (13)	0.0337 (14)	−0.0057 (11)	0.0044 (11)	−0.0067 (11)
Cd1	0.02621 (11)	0.03603 (12)	0.04251 (12)	−0.01089 (8)	0.00477 (8)	−0.00660 (10)
Cl1	0.0287 (3)	0.0578 (4)	0.0431 (4)	−0.0050 (3)	0.0039 (3)	0.0038 (3)
Cl2	0.0364 (4)	0.0389 (4)	0.0533 (4)	−0.0110 (3)	0.0141 (3)	−0.0121 (3)
N1	0.0256 (11)	0.0377 (13)	0.0396 (13)	−0.0070 (9)	0.0014 (10)	0.0005 (10)
N2	0.0336 (13)	0.0449 (14)	0.0375 (13)	−0.0157 (11)	0.0039 (10)	0.0001 (11)
N3	0.0265 (12)	0.0396 (13)	0.0380 (13)	−0.0141 (10)	0.0039 (10)	−0.0025 (10)
N4	0.0288 (12)	0.0355 (13)	0.0330 (12)	−0.0111 (10)	0.0039 (9)	−0.0015 (10)

C1—N1	1.389 (3)	C9—C14	1.403 (3)
C1—C2	1.393 (4)	C10—C11	1.373 (4)
C1—C6	1.399 (4)	C10—H10	0.9300
C2—C3	1.372 (4)	C11—C12	1.403 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (5)	C12—C13	1.370 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.371 (4)	C13—C14	1.393 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.386 (4)	C14—N4	1.389 (3)
C5—H5	0.9300	Cd1—N4	2.305 (2)
C6—N2	1.381 (3)	Cd1—N1	2.338 (2)
C7—N1	1.317 (3)	Cd1—Cl2	2.4602 (8)
C7—N2	1.341 (3)	Cd1—Cl1	2.5725 (10)
C7—C8	1.450 (4)	Cd1—Cl1i	2.5903 (10)
C8—N4	1.327 (3)	Cl1—Cd1i	2.5903 (10)
C8—N3	1.348 (3)	N2—H15	0.8600
C9—N3	1.385 (3)	N3—H16	0.8600
C9—C10	1.387 (4)
N1—C1—C2	131.0 (3)	C13—C12—C11	121.7 (3)
N1—C1—C6	108.9 (2)	C13—C12—H12	119.1
C2—C1—C6	120.1 (3)	C11—C12—H12	119.1
C3—C2—C1	117.6 (3)	C12—C13—C14	117.4 (3)
C3—C2—H2	121.2	C12—C13—H13	121.3
C1—C2—H2	121.2	C14—C13—H13	121.3
C2—C3—C4	121.8 (3)	N4—C14—C13	130.9 (2)
C2—C3—H3	119.1	N4—C14—C9	109.0 (2)
C4—C3—H3	119.1	C13—C14—C9	120.2 (3)
C5—C4—C3	121.3 (3)	N4—Cd1—N1	73.49 (8)
C5—C4—H4	119.3	N4—Cd1—Cl2	118.63 (6)
C3—C4—H4	119.3	N1—Cd1—Cl2	102.95 (6)
C4—C5—C6	117.4 (3)	N4—Cd1—Cl1	144.04 (6)
C4—C5—H5	121.3	N1—Cd1—Cl1	93.11 (6)
C6—C5—H5	121.3	Cl2—Cd1—Cl1	96.65 (3)
N2—C6—C5	132.8 (3)	N4—Cd1—Cl1i	91.81 (6)
N2—C6—C1	105.5 (2)	N1—Cd1—Cl1i	154.49 (6)
C5—C6—C1	121.7 (3)	Cl2—Cd1—Cl1i	102.39 (3)
N1—C7—N2	113.1 (2)	Cl1—Cd1—Cl1i	86.78 (3)
N1—C7—C8	119.9 (2)	Cd1—Cl1—Cd1i	93.22 (3)
N2—C7—C8	127.0 (2)	C7—N1—C1	105.3 (2)
N4—C8—N3	112.6 (2)	C7—N1—Cd1	112.71 (17)
N4—C8—C7	120.4 (2)	C1—N1—Cd1	141.87 (18)
N3—C8—C7	127.1 (2)	C7—N2—C6	107.1 (2)
N3—C9—C10	131.9 (2)	C7—N2—H15	126.4
N3—C9—C14	105.5 (2)	C6—N2—H15	126.4
C10—C9—C14	122.5 (3)	C8—N3—C9	107.4 (2)
C11—C10—C9	116.2 (3)	C8—N3—H16	126.3
C11—C10—H10	121.9	C9—N3—H16	126.3
C9—C10—H10	121.9	C8—N4—C14	105.6 (2)
C10—C11—C12	122.0 (3)	C8—N4—Cd1	112.97 (16)
C10—C11—H11	119.0	C14—N4—Cd1	140.52 (16)
C12—C11—H11	119.0
N1—C1—C2—C3	179.2 (3)	C6—C1—N1—C7	1.1 (3)
C6—C1—C2—C3	−0.3 (5)	C2—C1—N1—Cd1	−2.8 (5)
C1—C2—C3—C4	1.3 (5)	C6—C1—N1—Cd1	176.7 (2)
C2—C3—C4—C5	−0.8 (5)	N4—Cd1—N1—C7	−4.14 (18)
C3—C4—C5—C6	−0.8 (5)	Cl2—Cd1—N1—C7	112.26 (18)
C4—C5—C6—N2	−178.4 (3)	Cl1—Cd1—N1—C7	−150.18 (18)
C4—C5—C6—C1	1.9 (5)	Cl1i—Cd1—N1—C7	−61.1 (2)
N1—C1—C6—N2	−0.7 (3)	N4—Cd1—N1—C1	−179.5 (3)
C2—C1—C6—N2	178.8 (3)	Cl2—Cd1—N1—C1	−63.1 (3)
N1—C1—C6—C5	179.1 (3)	Cl1—Cd1—N1—C1	34.5 (3)
C2—C1—C6—C5	−1.3 (4)	Cl1i—Cd1—N1—C1	123.5 (3)
N1—C7—C8—N4	5.0 (4)	N1—C7—N2—C6	0.7 (3)
N2—C7—C8—N4	−175.5 (3)	C8—C7—N2—C6	−178.9 (3)
N1—C7—C8—N3	−175.0 (3)	C5—C6—N2—C7	−179.7 (3)
N2—C7—C8—N3	4.6 (5)	C1—C6—N2—C7	0.0 (3)
N3—C9—C10—C11	178.9 (3)	N4—C8—N3—C9	−0.1 (3)
C14—C9—C10—C11	0.0 (4)	C7—C8—N3—C9	179.8 (3)
C9—C10—C11—C12	0.1 (5)	C10—C9—N3—C8	−178.9 (3)
C10—C11—C12—C13	−0.1 (5)	C14—C9—N3—C8	0.1 (3)
C11—C12—C13—C14	−0.2 (4)	N3—C8—N4—C14	0.1 (3)
C12—C13—C14—N4	−178.9 (3)	C7—C8—N4—C14	−179.9 (2)
C12—C13—C14—C9	0.4 (4)	N3—C8—N4—Cd1	171.44 (17)
N3—C9—C14—N4	0.0 (3)	C7—C8—N4—Cd1	−8.5 (3)
C10—C9—C14—N4	179.1 (2)	C13—C14—N4—C8	179.3 (3)
N3—C9—C14—C13	−179.5 (2)	C9—C14—N4—C8	0.0 (3)
C10—C9—C14—C13	−0.3 (4)	C13—C14—N4—Cd1	11.9 (5)
N4—Cd1—Cl1—Cd1i	88.65 (9)	C9—C14—N4—Cd1	−167.4 (2)
N1—Cd1—Cl1—Cd1i	154.46 (6)	N1—Cd1—N4—C8	6.56 (18)
Cl2—Cd1—Cl1—Cd1i	−102.11 (3)	Cl2—Cd1—N4—C8	−89.44 (19)
Cl1i—Cd1—Cl1—Cd1i	0.0	Cl1—Cd1—N4—C8	78.4 (2)
N2—C7—N1—C1	−1.1 (3)	Cl1i—Cd1—N4—C8	165.38 (18)
C8—C7—N1—C1	178.5 (2)	N1—Cd1—N4—C14	173.4 (3)
N2—C7—N1—Cd1	−178.16 (18)	Cl2—Cd1—N4—C14	77.4 (3)
C8—C7—N1—Cd1	1.4 (3)	Cl1—Cd1—N4—C14	−114.8 (3)
C2—C1—N1—C7	−178.4 (3)	Cl1i—Cd1—N4—C14	−27.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H16···Cl2ii	0.86	2.39	3.221 (2)	163

Cd1—N4	2.305 (2)
Cd1—N1	2.338 (2)
Cd1—Cl2	2.4602 (8)
Cd1—Cl1	2.5725 (10)
Cd1—Cl1i	2.5903 (10)

N4—Cd1—Cl2	118.63 (6)
N4—Cd1—Cl1	144.04 (6)
Cl2—Cd1—Cl1	96.65 (3)
N1—Cd1—Cl1i	154.49 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H16⋯Cl2ii	0.86	2.39	3.221 (2)	163

Symmetry code: (ii) .