Di-bromido-bis-(2-methyl-1H-benzimidazole-κN (3))cadmium.

In the title compound, [CdBr2(C8H8N2)2], the Cd(II) atom has a distorted tetra-hedral coordination formed by the two imino N atoms of two 2-methyl-benzimidazole ligands and two terminal bromide ligands. The Cd(II) atom is slightly out of the benzimidazole planes by 0.320 (3) and 0.210 (3) Å. The dihedral angle between the benzimidazole planes is 71.6 (2)°. In the crystal, mol-ecules are linked by N-H⋯Br hydrogen bonds into puckered layers parallel to (001).

Related literature

For background to benzimidazole, see: Roderick et al. (1972 ▶). For related crystal structures, see: Barros-García et al. (2005 ▶); Wang et al. (2010 ▶); Yang et al. (2011 ▶).

Experimental

Crystal data

[CdBr2(C8H8N2)2]

M = 536.54

Monoclinic,

a = 10.007 (9) Å

b = 14.747 (12) Å

c = 12.399 (11) Å

β = 93.088 (14)°

V = 1827 (3) Å3

Z = 4

Mo Kα radiation

μ = 5.57 mm−1

T = 296 K

0.22 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS Spider diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.374, T max = 0.469

9698 measured reflections

3585 independent reflections

2748 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.077

S = 1.00

3585 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −1.02 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024549/kq2008sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024549/kq2008Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024549/kq2008Isup3.cdx

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

[CdBr2(C8H8N2)2]	F(000) = 1032
Mr = 536.54	Dx = 1.951 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3275 reflections
a = 10.007 (9) Å	θ = 2.5–26.6°
b = 14.747 (12) Å	µ = 5.57 mm−1
c = 12.399 (11) Å	T = 296 K
β = 93.088 (14)°	Block, colorless
V = 1827 (3) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Rigaku R-AXIS Spider diffractometer	2748 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 26.0°, θmin = 2.0°
ω scans	h = −12→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→14
Tmin = 0.374, Tmax = 0.469	l = −15→14
9698 measured reflections	13 standard reflections every 0 reflections
3585 independent reflections	intensity decay: none

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) = 0.077	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0407P)2] where P = (Fo2 + 2Fc2)/3
3585 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −1.02 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
N1	0.3592 (3)	0.96335 (19)	0.8577 (2)	0.0362 (7)
N2	0.5028 (4)	0.8661 (2)	0.9341 (3)	0.0485 (9)
H2	0.5712	0.8311	0.9428	0.058*
N3	0.0723 (3)	1.01679 (18)	0.6820 (2)	0.0339 (7)
N4	−0.1049 (3)	0.93220 (19)	0.6357 (2)	0.0417 (8)
H4	−0.1554	0.8851	0.6290	0.050*
Br1	0.40130 (5)	1.14156 (3)	0.60773 (4)	0.06071 (16)
Br2	0.20546 (5)	1.20099 (3)	0.88850 (4)	0.06367 (17)
C1	0.4087 (4)	0.8806 (2)	1.0086 (3)	0.0409 (9)
C2	0.3939 (5)	0.8457 (3)	1.1109 (3)	0.0531 (12)
H2A	0.4561	0.8060	1.1434	0.064*
C3	0.2816 (6)	0.8730 (3)	1.1622 (4)	0.0626 (14)
H3	0.2681	0.8511	1.2311	0.075*
C4	0.1873 (6)	0.9326 (3)	1.1139 (4)	0.0633 (13)
H4A	0.1119	0.9482	1.1505	0.076*
C5	0.2045 (5)	0.9687 (3)	1.0127 (3)	0.0535 (11)
H5	0.1432	1.0094	0.9812	0.064*
C6	0.3175 (4)	0.9417 (2)	0.9597 (3)	0.0368 (9)
C7	0.4708 (4)	0.9156 (2)	0.8454 (3)	0.0408 (9)
C8	0.5489 (5)	0.9139 (3)	0.7478 (4)	0.0620 (13)
H8A	0.4935	0.9338	0.6867	0.093*
H8B	0.5793	0.8532	0.7355	0.093*
H8C	0.6246	0.9536	0.7578	0.093*
C9	−0.0236 (4)	1.0707 (2)	0.6250 (3)	0.0332 (8)
C10	−0.0180 (4)	1.1618 (2)	0.5961 (3)	0.0420 (9)
H10	0.0571	1.1972	0.6131	0.050*
C11	−0.1303 (5)	1.1972 (3)	0.5406 (3)	0.0502 (11)
H11	−0.1297	1.2575	0.5187	0.060*
C12	−0.2441 (5)	1.1449 (3)	0.5168 (3)	0.0531 (11)
H12	−0.3184	1.1720	0.4820	0.064*
C13	−0.2499 (4)	1.0548 (3)	0.5431 (3)	0.0482 (10)
H13	−0.3255	1.0199	0.5259	0.058*
C14	−0.1372 (4)	1.0184 (2)	0.5966 (3)	0.0364 (9)
C15	0.0180 (4)	0.9343 (2)	0.6856 (3)	0.0386 (9)
C16	0.0818 (5)	0.8531 (2)	0.7384 (3)	0.0577 (13)
H16A	0.1749	0.8514	0.7233	0.087*
H16B	0.0384	0.7992	0.7108	0.087*
H16C	0.0733	0.8566	0.8150	0.087*
Cd1	0.26490 (3)	1.074421 (18)	0.75481 (2)	0.03930 (11)

	U11	U22	U33	U12	U13	U23
N1	0.039 (2)	0.0255 (15)	0.0436 (18)	0.0043 (14)	0.0033 (15)	0.0002 (14)
N2	0.044 (2)	0.0340 (18)	0.066 (2)	0.0133 (15)	−0.0060 (18)	0.0078 (17)
N3	0.0365 (18)	0.0242 (15)	0.0410 (16)	−0.0068 (13)	0.0015 (14)	−0.0021 (13)
N4	0.048 (2)	0.0289 (17)	0.0482 (19)	−0.0128 (14)	0.0016 (16)	−0.0055 (14)
Br1	0.0653 (3)	0.0460 (3)	0.0713 (3)	−0.0150 (2)	0.0077 (2)	0.0149 (2)
Br2	0.0746 (4)	0.0398 (3)	0.0745 (3)	0.0205 (2)	−0.0163 (3)	−0.0179 (2)
C1	0.044 (2)	0.027 (2)	0.050 (2)	−0.0007 (17)	−0.010 (2)	0.0000 (18)
C2	0.066 (3)	0.039 (2)	0.053 (3)	−0.008 (2)	−0.017 (2)	0.006 (2)
C3	0.089 (4)	0.058 (3)	0.041 (2)	−0.018 (3)	0.003 (3)	−0.003 (2)
C4	0.082 (4)	0.057 (3)	0.052 (3)	0.005 (3)	0.016 (3)	−0.005 (2)
C5	0.058 (3)	0.049 (3)	0.053 (3)	0.016 (2)	0.002 (2)	−0.003 (2)
C6	0.043 (2)	0.0256 (19)	0.041 (2)	−0.0001 (16)	0.0017 (18)	−0.0006 (16)
C7	0.039 (2)	0.030 (2)	0.053 (2)	0.0008 (17)	0.0057 (19)	−0.0037 (18)
C8	0.057 (3)	0.050 (3)	0.081 (3)	0.006 (2)	0.027 (3)	−0.005 (2)
C9	0.037 (2)	0.030 (2)	0.0328 (19)	0.0039 (16)	0.0046 (16)	−0.0025 (16)
C10	0.046 (3)	0.033 (2)	0.048 (2)	−0.0044 (18)	0.0004 (19)	−0.0034 (18)
C11	0.068 (3)	0.029 (2)	0.053 (2)	0.013 (2)	−0.003 (2)	−0.0004 (19)
C12	0.051 (3)	0.054 (3)	0.053 (3)	0.013 (2)	−0.010 (2)	−0.006 (2)
C13	0.041 (3)	0.053 (3)	0.050 (2)	−0.004 (2)	−0.005 (2)	−0.011 (2)
C14	0.041 (2)	0.035 (2)	0.0341 (19)	−0.0006 (17)	0.0046 (17)	−0.0080 (16)
C15	0.051 (3)	0.028 (2)	0.038 (2)	−0.0037 (17)	0.0054 (19)	0.0007 (16)
C16	0.082 (4)	0.030 (2)	0.059 (3)	−0.008 (2)	−0.014 (2)	0.011 (2)
Cd1	0.04113 (19)	0.02686 (16)	0.04918 (18)	0.00061 (12)	−0.00430 (13)	0.00266 (12)

N1—C7	1.336 (5)	C4—H4A	0.9300
N1—C6	1.390 (5)	C5—C6	1.396 (6)
N1—Cd1	2.252 (3)	C5—H5	0.9300
N2—C7	1.345 (5)	C7—C8	1.475 (6)
N2—C1	1.370 (5)	C8—H8A	0.9600
N2—H2	0.8600	C8—H8B	0.9600
N3—C15	1.334 (4)	C8—H8C	0.9600
N3—C9	1.407 (5)	C9—C10	1.393 (5)
N3—Cd1	2.250 (3)	C9—C14	1.403 (5)
N4—C15	1.347 (5)	C10—C11	1.387 (6)
N4—C14	1.392 (5)	C10—H10	0.9300
N4—H4	0.8600	C11—C12	1.394 (6)
Br1—Cd1	2.5372 (15)	C11—H11	0.9300
Br2—Cd1	2.5869 (15)	C12—C13	1.370 (6)
C1—C2	1.385 (6)	C12—H12	0.9300
C1—C6	1.398 (5)	C13—C14	1.386 (6)
C2—C3	1.381 (7)	C13—H13	0.9300
C2—H2A	0.9300	C15—C16	1.492 (5)
C3—C4	1.401 (7)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.381 (6)	C16—H16C	0.9600
C7—N1—C6	106.1 (3)	C7—C8—H8C	109.5
C7—N1—Cd1	130.2 (3)	H8A—C8—H8C	109.5
C6—N1—Cd1	123.1 (2)	H8B—C8—H8C	109.5
C7—N2—C1	109.0 (3)	C10—C9—C14	120.6 (4)
C7—N2—H2	125.5	C10—C9—N3	129.7 (4)
C1—N2—H2	125.5	C14—C9—N3	109.7 (3)
C15—N3—C9	105.3 (3)	C11—C10—C9	116.6 (4)
C15—N3—Cd1	132.3 (3)	C11—C10—H10	121.7
C9—N3—Cd1	122.3 (2)	C9—C10—H10	121.7
C15—N4—C14	109.1 (3)	C10—C11—C12	121.9 (4)
C15—N4—H4	125.4	C10—C11—H11	119.1
C14—N4—H4	125.4	C12—C11—H11	119.1
N2—C1—C2	132.2 (4)	C13—C12—C11	122.1 (4)
N2—C1—C6	105.3 (3)	C13—C12—H12	119.0
C2—C1—C6	122.5 (4)	C11—C12—H12	119.0
C3—C2—C1	116.3 (4)	C12—C13—C14	116.5 (4)
C3—C2—H2A	121.8	C12—C13—H13	121.8
C1—C2—H2A	121.8	C14—C13—H13	121.8
C2—C3—C4	122.2 (4)	C13—C14—N4	133.4 (4)
C2—C3—H3	118.9	C13—C14—C9	122.3 (4)
C4—C3—H3	118.9	N4—C14—C9	104.2 (3)
C5—C4—C3	121.0 (5)	N3—C15—N4	111.7 (3)
C5—C4—H4A	119.5	N3—C15—C16	125.5 (4)
C3—C4—H4A	119.5	N4—C15—C16	122.8 (3)
C4—C5—C6	117.5 (4)	C15—C16—H16A	109.5
C4—C5—H5	121.2	C15—C16—H16B	109.5
C6—C5—H5	121.2	H16A—C16—H16B	109.5
N1—C6—C5	130.8 (4)	C15—C16—H16C	109.5
N1—C6—C1	108.8 (3)	H16A—C16—H16C	109.5
C5—C6—C1	120.4 (4)	H16B—C16—H16C	109.5
N1—C7—N2	110.8 (3)	N3—Cd1—N1	106.04 (12)
N1—C7—C8	125.9 (4)	N3—Cd1—Br1	109.95 (9)
N2—C7—C8	123.3 (4)	N1—Cd1—Br1	117.77 (9)
C7—C8—H8A	109.5	N3—Cd1—Br2	107.95 (9)
C7—C8—H8B	109.5	N1—Cd1—Br2	105.40 (9)
H8A—C8—H8B	109.5	Br1—Cd1—Br2	109.28 (2)
C7—N2—C1—C2	178.9 (4)	C9—C10—C11—C12	1.2 (6)
C7—N2—C1—C6	0.1 (4)	C10—C11—C12—C13	−2.5 (7)
N2—C1—C2—C3	−177.2 (4)	C11—C12—C13—C14	1.1 (6)
C6—C1—C2—C3	1.3 (6)	C12—C13—C14—N4	−179.9 (4)
C1—C2—C3—C4	0.1 (7)	C12—C13—C14—C9	1.4 (6)
C2—C3—C4—C5	−1.5 (7)	C15—N4—C14—C13	−177.7 (4)
C3—C4—C5—C6	1.5 (7)	C15—N4—C14—C9	1.2 (4)
C7—N1—C6—C5	−177.1 (4)	C10—C9—C14—C13	−2.7 (6)
Cd1—N1—C6—C5	11.3 (6)	N3—C9—C14—C13	177.7 (3)
C7—N1—C6—C1	0.9 (4)	C10—C9—C14—N4	178.3 (3)
Cd1—N1—C6—C1	−170.7 (2)	N3—C9—C14—N4	−1.4 (4)
C4—C5—C6—N1	177.6 (4)	C9—N3—C15—N4	−0.2 (4)
C4—C5—C6—C1	−0.2 (6)	Cd1—N3—C15—N4	175.6 (2)
N2—C1—C6—N1	−0.6 (4)	C9—N3—C15—C16	−179.7 (4)
C2—C1—C6—N1	−179.5 (3)	Cd1—N3—C15—C16	−3.9 (6)
N2—C1—C6—C5	177.6 (4)	C14—N4—C15—N3	−0.6 (4)
C2—C1—C6—C5	−1.3 (6)	C14—N4—C15—C16	178.9 (4)
C6—N1—C7—N2	−0.9 (4)	C15—N3—Cd1—N1	−4.6 (3)
Cd1—N1—C7—N2	169.9 (2)	C9—N3—Cd1—N1	170.6 (2)
C6—N1—C7—C8	177.7 (4)	C15—N3—Cd1—Br1	123.7 (3)
Cd1—N1—C7—C8	−11.5 (6)	C9—N3—Cd1—Br1	−61.0 (3)
C1—N2—C7—N1	0.5 (4)	C15—N3—Cd1—Br2	−117.1 (3)
C1—N2—C7—C8	−178.1 (4)	C9—N3—Cd1—Br2	58.1 (3)
C15—N3—C9—C10	−178.6 (4)	C7—N1—Cd1—N3	112.4 (3)
Cd1—N3—C9—C10	5.1 (5)	C6—N1—Cd1—N3	−78.2 (3)
C15—N3—C9—C14	1.0 (4)	C7—N1—Cd1—Br1	−11.1 (4)
Cd1—N3—C9—C14	−175.3 (2)	C6—N1—Cd1—Br1	158.3 (2)
C14—C9—C10—C11	1.3 (5)	C7—N1—Cd1—Br2	−133.3 (3)
N3—C9—C10—C11	−179.1 (3)	C6—N1—Cd1—Br2	36.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br1i	0.86	2.88	3.495 (4)	130
N4—H4···Br2ii	0.86	2.77	3.563 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Br1i	0.86	2.88	3.495 (4)	130
N4—H4⋯Br2ii	0.86	2.77	3.563 (4)	155

Symmetry codes: (i) ; (ii) .