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

Liu, G.

doi:10.1107/S1600536808040968

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m37

doi:10.1107/S1600536808040968

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

Ge Liu ^a ^*

^aChifeng University, Chifeng 024000, People's Republic of China
^*Correspondence e-mail: liu_ge2008@163.com

(Received 26 November 2008; accepted 4 December 2008; online 10 December 2008)

The title binuclear complex, [Cd₂Cl₄(C₁₄H₁₀N₄)₂], was synthesized by the hydrothermal reaction of CdCl₂ and the ligand 2,2′-bibenzimidazole. The molecule 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 intermolecular N—H⋯Cl hydrogen bonds, resulting in a one-dimensional supramolecular structure.

Related literature

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

Experimental

Crystal data

[Cd₂Cl₄(C₁₄H₁₀N₄)₂]
M_r = 835.12
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.060
S = 1.14
3337 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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) -x+2, -y+2, -z+1.

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) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Bibenzimidazole has the potential to function as a bis-bidentate nitrogen ligand by coordinating to metal ions as a chelate. On the other hand, Cd^II-containing coordination polymers have attracted much attention as they are able to bond to different donors ligands simultaneously, because of the Cd^II large radius. Various coordination modes and potential applications in catalysis, fluorescent materials, NLO materials and so on (Meng et al. 2004) have been described. Here we report the crystal structure of the title complex prepared from CdCl₂ and bibenzimidazole ligand (see experimental).

As show in Fig. 1, the complex lies on an inversion center, and Cd atoms have strongly distorted trigonal-bipyramidal geometry, being coordinated by two N atoms from the organic ligand, and by one terminal and two bridging Cl^- anions. The two Cd centers are bridged by two chloride ions to give a dinuclear cadmium complex. Intermolecular N—H···Cl hydrogen bonds extend the dinuclear complex to a one dimensional chain in the crystal structure (Fig. 2).

Related literature top

For the synthesis of 2,2'-bibenzimidazole, see: Fieselmann et al. (1978). For general properties of Cd^II-based complex polymers, see: Meng et al. (2004).

Experimental top

A mixture of CdCl₂ (0.073 g, 0.40 mmol), bibenzimidazole (0.070 g, 0.30 mmol) and H₂O (10 ml) was placed in a Teflon reactor, then heated to 433 K at 10.8 K/h; after maintaining the reaction at 433 K for three days, it was cooled to 303 K at 10.8 K/h. Crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick,2008).

Figures top

	Fig. 1. The structure of the title compound with displacement ellipsoids at the 30% probability level.
	Fig. 2. One dimensional chain formed by hydrogen bonds (dashed lines) in the crystal structure of the title compound.

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

Crystal data top

[Cd₂Cl₄(C₁₄H₁₀N₄)₂]	F(000) = 1632
M_r = 835.12	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0213P)² + 2.9529P] where P = (F_o² + 2F_c²)/3
3337 reflections	(Δ/σ)_max = 0.002
190 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Cd₂Cl₄(C₁₄H₁₀N₄)₂]	V = 2910.1 (10) Å³
M_r = 835.12	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.824 (2) Å	µ = 1.86 mm⁻¹
b = 10.784 (2) Å	T = 293 K
c = 22.828 (5) Å	0.17 × 0.16 × 0.12 mm
β = 91.10 (3)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	2840 reflections with I > 2σ(I)
14677 measured reflections	R_int = 0.035
3337 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 1.14	Δρ_max = 0.29 e Å⁻³
3337 reflections	Δρ_min = −0.34 e Å⁻³
190 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Cd₂Cl₄(C₁₄H₁₀N₄)₂]
M_r	835.12
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	11.824 (2), 10.784 (2), 22.828 (5)
β (°)	91.10 (3)
V (Å³)	2910.1 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.17 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14677, 3337, 2840
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.060, 1.14
No. of reflections	3337
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick,2008), SHELXL97 (Sheldrick,2008), SHELXTL (Sheldrick,2008).

Selected geometric parameters (Å, º) top

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

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

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H16···Cl2ⁱⁱ	0.86	2.39	3.221 (2)	163.0

Symmetry code: (ii) x−1/2, y−1/2, z.

Acknowledgements

The author thanks Chifeng University for supporting this work.

References

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