Dibromido[1,1′-dibenzyl-2,2′-(sulfane­diyl­dimethyl­ene)di-1H-benzimidazole]­cadmium(II) dimethyl­formamide solvate

Wang, K.; Yuan, J.; Chen, G.; Chen, Q.; Wu, H.

doi:10.1107/S1600536810028448

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m993

https://doi.org/10.1107/S1600536810028448

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Dibromido[1,1′-dibenzyl-2,2′-(sulfanediyldimethylene)di-1H-benzimidazole]cadmium(II) dimethylformamide solvate

Kaitong Wang,^a Jingkun Yuan,^a Guisheng Chen,^a Qian Chen ^a and Huilu Wu ^a ^*

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wuhuilu@163.com

(Received 11 July 2010; accepted 16 July 2010; online 21 July 2010)

In the title compound, [CdBr₂(C₃₀H₂₆N₄S)]·C₃H₇NO, both the complex and solvent molecule lie on a crystallographic mirror plane. The Cd^II ion is coordinated in a disorted square-pyramidal CdBr₂N₂S environment with one of the Br atoms in the apical site. In the crystal structure, the benzimidazole ring systems are involved in weak intermolecular π–π stacking interactions [centroid–centroid distances = 3.606 (2) and 3.753 (2) Å]. Further stabilization is provided by weak intermolecular C—H⋯O hydrogen bonds. The methyl H atoms of the dimethylformamide solvent molecule are disordered about a mirror plane.

Related literature

For background to the synthesis and for related structures of 1,3-bis(benzimidazol-2-yl)-2-thiapropane and its derivatives, see: Dagdigian et al. (1979 ); Agh-Atabay et al.(2004 ); Wu et al. (2009 ).

Experimental

Crystal data

[CdBr₂(C₃₀H₂₆N₄S)]·C₃H₇NO
M_r = 819.92
Monoclinic, P 2₁ /m
a = 9.7437 (8) Å
b = 16.7792 (14) Å
c = 10.5931 (9) Å
β = 110.029 (1)°
V = 1627.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 3.23 mm⁻¹
T = 296 K
0.36 × 0.32 × 0.28 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.390, T_max = 0.465
9062 measured reflections
3305 independent reflections
2742 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.077
S = 1.05
3305 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1ⁱ	0.97	2.38	3.004 (5)	122
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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 global, I. DOI: https://doi.org/10.1107/S1600536810028448/lh5084sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028448/lh5084Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title complex is shown in Fig. 1. The Cd^II ion is coordinated by one tridentate 1,3-bis(1-benzylbenzimidazol-2-yl)-2-thiapropane ligand and two bromide ions in a distorted square-pyramidal geometry. In the crystal structure, the benzimidazole ring systems are involved in weak intermolecular π–π stacking interactions [centroid–centroid distances = 3.606 (2) and 3.753 (2) Å].

Related literature top

Experimental top

To a stirred solution of 1,3-bis(1-benzylbenzimidazol-2-yl)-2-thiapropane (0.237 g, 0.50 mmol) in hot MeOH (10 ml) was added Cd(C₆H₂N₃O₇)₂ (0.154 g, 0.25 mmol) and KBr(0.059 g, 0.50 mmol) in MeOH (5 ml). A yellow crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et₂O, and dried in vacuo. The dried precipitate was dissolved in DMF resulting in a yellow solution. The deep yellow crystals suitable for X-ray diffraction studies were obtained by ether diffusion into a solution of the title compound in DMF after several days at room temperature. Yield, 0.29 g (73%). (found: C, 54.16; H, 4.49; N,9.63. Calcd.: C, 54.22; H, 4.55; N, 9.58)

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity [symmetry code (A): x, -y+1/2, z].

Dibromido[1,1'-dibenzyl-2,2'-(sulfanediyldimethylene)di-1H- benzimidazole]cadmium(II) dimethylformamide solvate top

Crystal data top

[CdBr₂(C₃₀H₂₆N₄S)]·C₃H₇NO	F(000) = 816
M_r = 819.92	D_x = 1.674 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 3975 reflections
a = 9.7437 (8) Å	θ = 2.2–27.3°
b = 16.7792 (14) Å	µ = 3.23 mm⁻¹
c = 10.5931 (9) Å	T = 296 K
β = 110.029 (1)°	Block, yellow
V = 1627.1 (2) Å³	0.36 × 0.32 × 0.28 mm
Z = 2

Data collection top

Bruker APEXII area-detector diffractometer	3305 independent reflections
Radiation source: fine-focus sealed tube	2742 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→12
T_min = 0.390, T_max = 0.465	k = −20→20
9062 measured reflections	l = −13→6

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0374P)² + 0.7961P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3305 reflections	Δρ_max = 0.78 e Å⁻³
211 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (4)

Crystal data top

[CdBr₂(C₃₀H₂₆N₄S)]·C₃H₇NO	V = 1627.1 (2) Å³
M_r = 819.92	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 9.7437 (8) Å	µ = 3.23 mm⁻¹
b = 16.7792 (14) Å	T = 296 K
c = 10.5931 (9) Å	0.36 × 0.32 × 0.28 mm
β = 110.029 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3305 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2742 reflections with I > 2σ(I)
T_min = 0.390, T_max = 0.465	R_int = 0.027
9062 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.05	Δρ_max = 0.78 e Å⁻³
3305 reflections	Δρ_min = −0.64 e Å⁻³
211 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.53761 (5)	0.2500	0.42042 (5)	0.05529 (15)
Br2	0.95622 (6)	0.2500	0.72708 (5)	0.05828 (15)
C1	1.0172 (3)	0.16482 (17)	0.2726 (3)	0.0434 (7)
H1A	0.9562	0.1832	0.1844	0.052*
H1B	1.1010	0.1377	0.2630	0.052*
C2	0.9329 (3)	0.10786 (16)	0.3253 (3)	0.0343 (6)
C3	0.9688 (3)	−0.01196 (18)	0.1929 (3)	0.0410 (7)
H3A	1.0153	−0.0620	0.2295	0.049*
H3B	1.0400	0.0207	0.1714	0.049*
C4	0.8399 (3)	−0.02804 (19)	0.0656 (3)	0.0444 (7)
C5	0.7349 (5)	0.0278 (3)	0.0121 (4)	0.0949 (16)
H5	0.7429	0.0777	0.0523	0.114*
C6	0.6156 (6)	0.0109 (4)	−0.1025 (5)	0.117 (2)
H6	0.5439	0.0493	−0.1376	0.140*
C7	0.6033 (5)	−0.0607 (3)	−0.1629 (4)	0.0825 (13)
H7	0.5234	−0.0716	−0.2395	0.099*
C8	0.7068 (5)	−0.1163 (3)	−0.1119 (3)	0.0691 (11)
H8	0.6985	−0.1656	−0.1539	0.083*
C9	0.8260 (4)	−0.1008 (2)	0.0029 (3)	0.0545 (8)
H9	0.8967	−0.1398	0.0376	0.065*
C10	0.8378 (3)	−0.00630 (16)	0.3597 (3)	0.0343 (6)
C11	0.7924 (3)	−0.08440 (17)	0.3631 (3)	0.0432 (7)
H11	0.8186	−0.1248	0.3157	0.052*
C12	0.7067 (3)	−0.09879 (19)	0.4403 (3)	0.0491 (7)
H12	0.6721	−0.1501	0.4436	0.059*
C13	0.6703 (3)	−0.03818 (19)	0.5139 (3)	0.0468 (7)
H13	0.6136	−0.0506	0.5662	0.056*
C14	0.7157 (3)	0.03915 (18)	0.5110 (3)	0.0421 (7)
H14	0.6912	0.0791	0.5603	0.051*
C15	0.8005 (3)	0.05523 (17)	0.4308 (3)	0.0351 (6)
C16	0.6054 (6)	0.2500	1.0757 (6)	0.0683 (14)
H16	0.5334	0.2500	1.1148	0.082*
C17	0.4073 (8)	0.2500	0.8662 (7)	0.111 (3)
H17A	0.3912	0.2763	0.7819	0.166*	0.50
H17B	0.3553	0.2776	0.9152	0.166*	0.50
H17C	0.3728	0.1961	0.8502	0.166*	0.50
C18	0.6637 (11)	0.2500	0.8761 (10)	0.133 (3)
H18A	0.6547	0.2014	0.8260	0.199*	0.50
H18B	0.7607	0.2540	0.9405	0.199*	0.50
H18C	0.6452	0.2946	0.8158	0.199*	0.50
Cd1	0.81788 (3)	0.2500	0.46873 (3)	0.04091 (11)
N1	0.8612 (2)	0.12589 (13)	0.4073 (2)	0.0359 (5)
N2	0.9223 (2)	0.02893 (13)	0.2940 (2)	0.0355 (5)
N3	0.5618 (5)	0.2500	0.9435 (5)	0.0682 (12)
O1	0.7309 (5)	0.2500	1.1506 (5)	0.1167 (18)
S1	1.07918 (11)	0.2500	0.38353 (10)	0.0414 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0422 (3)	0.0582 (3)	0.0688 (3)	0.000	0.0232 (2)	0.000
Br2	0.0716 (3)	0.0552 (3)	0.0480 (3)	0.000	0.0204 (2)	0.000
C1	0.0503 (17)	0.0394 (16)	0.0495 (16)	−0.0028 (13)	0.0285 (14)	−0.0058 (13)
C2	0.0313 (13)	0.0363 (15)	0.0343 (13)	0.0002 (11)	0.0099 (11)	−0.0025 (11)
C3	0.0445 (16)	0.0412 (16)	0.0406 (15)	0.0036 (13)	0.0189 (13)	−0.0089 (12)
C4	0.0488 (17)	0.0510 (18)	0.0343 (15)	0.0001 (14)	0.0156 (13)	−0.0017 (12)
C5	0.096 (3)	0.082 (3)	0.070 (3)	0.035 (3)	−0.018 (2)	−0.023 (2)
C6	0.099 (4)	0.139 (5)	0.071 (3)	0.049 (4)	−0.023 (3)	−0.013 (3)
C7	0.067 (3)	0.132 (4)	0.041 (2)	−0.013 (3)	0.0088 (18)	−0.010 (2)
C8	0.083 (3)	0.081 (3)	0.0469 (19)	−0.034 (2)	0.027 (2)	−0.0184 (19)
C9	0.066 (2)	0.055 (2)	0.0441 (17)	−0.0117 (16)	0.0214 (16)	−0.0056 (14)
C10	0.0282 (13)	0.0381 (14)	0.0342 (14)	0.0013 (11)	0.0075 (11)	0.0008 (11)
C11	0.0428 (16)	0.0383 (16)	0.0468 (16)	0.0023 (13)	0.0131 (13)	0.0017 (13)
C12	0.0426 (16)	0.0401 (17)	0.0612 (19)	−0.0004 (13)	0.0134 (15)	0.0135 (14)
C13	0.0357 (15)	0.0560 (19)	0.0510 (18)	0.0053 (14)	0.0179 (14)	0.0176 (14)
C14	0.0362 (14)	0.0488 (17)	0.0434 (16)	0.0070 (13)	0.0164 (13)	0.0046 (13)
C15	0.0268 (13)	0.0409 (15)	0.0353 (14)	0.0014 (11)	0.0077 (11)	0.0006 (11)
C16	0.049 (3)	0.071 (4)	0.077 (4)	0.000	0.011 (3)	0.000
C17	0.075 (5)	0.161 (8)	0.077 (4)	0.000	0.001 (4)	0.000
C18	0.134 (8)	0.157 (9)	0.136 (7)	0.000	0.083 (6)	0.000
Cd1	0.04412 (19)	0.03567 (18)	0.0520 (2)	0.000	0.02820 (15)	0.000
N1	0.0345 (12)	0.0377 (12)	0.0394 (12)	−0.0018 (10)	0.0175 (10)	−0.0041 (10)
N2	0.0356 (12)	0.0363 (12)	0.0355 (12)	−0.0006 (10)	0.0132 (10)	−0.0036 (9)
N3	0.057 (3)	0.073 (3)	0.073 (3)	0.000	0.020 (2)	0.000
O1	0.062 (3)	0.149 (5)	0.116 (4)	0.000	0.002 (3)	0.000
S1	0.0379 (5)	0.0342 (5)	0.0486 (6)	0.000	0.0104 (4)	0.000

Geometric parameters (Å, º) top

Br1—Cd1	2.6004 (6)	C10—C15	1.397 (4)
Br2—Cd1	2.6038 (6)	C11—C12	1.376 (4)
C1—C2	1.488 (4)	C11—H11	0.9300
C1—S1	1.817 (3)	C12—C13	1.399 (5)
C1—H1A	0.9700	C12—H12	0.9300
C1—H1B	0.9700	C13—C14	1.375 (4)
C2—N1	1.322 (3)	C13—H13	0.9300
C2—N2	1.360 (3)	C14—C15	1.399 (4)
C3—N2	1.468 (3)	C14—H14	0.9300
C3—C4	1.519 (4)	C15—N1	1.385 (3)
C3—H3A	0.9700	C16—O1	1.208 (7)
C3—H3B	0.9700	C16—N3	1.316 (7)
C4—C5	1.360 (5)	C16—H16	0.9300
C4—C9	1.374 (4)	C17—N3	1.446 (8)
C5—C6	1.393 (6)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—C7	1.347 (7)	C17—H17C	0.9600
C6—H6	0.9300	C18—N3	1.408 (9)
C7—C8	1.344 (6)	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.389 (5)	C18—H18C	0.9600
C8—H8	0.9300	Cd1—N1	2.264 (2)
C9—H9	0.9300	Cd1—N1ⁱ	2.264 (2)
C10—N2	1.380 (3)	Cd1—S1	2.9784 (11)
C10—C11	1.387 (4)	S1—C1ⁱ	1.817 (3)

C2—C1—S1	111.48 (19)	C12—C13—H13	119.1
C2—C1—H1A	109.3	C13—C14—C15	117.2 (3)
S1—C1—H1A	109.3	C13—C14—H14	121.4
C2—C1—H1B	109.3	C15—C14—H14	121.4
S1—C1—H1B	109.3	N1—C15—C10	109.2 (2)
H1A—C1—H1B	108.0	N1—C15—C14	130.7 (3)
N1—C2—N2	111.7 (2)	C10—C15—C14	120.1 (3)
N1—C2—C1	125.7 (2)	O1—C16—N3	125.8 (6)
N2—C2—C1	122.6 (2)	O1—C16—H16	117.1
N2—C3—C4	111.3 (2)	N3—C16—H16	117.1
N2—C3—H3A	109.4	N3—C17—H17A	109.5
C4—C3—H3A	109.4	N3—C17—H17B	109.5
N2—C3—H3B	109.4	H17A—C17—H17B	109.5
C4—C3—H3B	109.4	N3—C17—H17C	109.5
H3A—C3—H3B	108.0	H17A—C17—H17C	109.5
C5—C4—C9	118.4 (3)	H17B—C17—H17C	109.5
C5—C4—C3	121.5 (3)	N3—C18—H18A	109.5
C9—C4—C3	120.1 (3)	N3—C18—H18B	109.5
C4—C5—C6	120.4 (4)	H18A—C18—H18B	109.5
C4—C5—H5	119.8	N3—C18—H18C	109.5
C6—C5—H5	119.8	H18A—C18—H18C	109.5
C7—C6—C5	120.6 (5)	H18B—C18—H18C	109.5
C7—C6—H6	119.7	N1—Cd1—N1ⁱ	133.74 (11)
C5—C6—H6	119.7	N1—Cd1—Br1	103.31 (6)
C8—C7—C6	119.7 (4)	N1ⁱ—Cd1—Br1	103.31 (6)
C8—C7—H7	120.2	N1—Cd1—Br2	102.82 (6)
C6—C7—H7	120.2	N1ⁱ—Cd1—Br2	102.82 (6)
C7—C8—C9	120.6 (4)	Br1—Cd1—Br2	109.732 (19)
C7—C8—H8	119.7	N1—Cd1—S1	69.50 (5)
C9—C8—H8	119.7	N1ⁱ—Cd1—S1	69.50 (5)
C4—C9—C8	120.3 (4)	Br1—Cd1—S1	152.80 (3)
C4—C9—H9	119.9	Br2—Cd1—S1	97.46 (3)
C8—C9—H9	119.9	C2—N1—C15	106.0 (2)
N2—C10—C11	131.9 (3)	C2—N1—Cd1	126.29 (18)
N2—C10—C15	105.4 (2)	C15—N1—Cd1	127.02 (17)
C11—C10—C15	122.7 (3)	C2—N2—C10	107.6 (2)
C12—C11—C10	116.4 (3)	C2—N2—C3	128.0 (2)
C12—C11—H11	121.8	C10—N2—C3	123.7 (2)
C10—C11—H11	121.8	C16—N3—C18	120.8 (6)
C11—C12—C13	121.7 (3)	C16—N3—C17	119.8 (5)
C11—C12—H12	119.2	C18—N3—C17	119.4 (6)
C13—C12—H12	119.2	C1ⁱ—S1—C1	103.7 (2)
C14—C13—C12	121.9 (3)	C1ⁱ—S1—Cd1	93.83 (10)
C14—C13—H13	119.1	C1—S1—Cd1	93.83 (10)

S1—C1—C2—N1	25.0 (4)	N1ⁱ—Cd1—N1—C2	5.0 (3)
S1—C1—C2—N2	−154.3 (2)	Br1—Cd1—N1—C2	128.6 (2)
N2—C3—C4—C5	42.8 (5)	Br2—Cd1—N1—C2	−117.2 (2)
N2—C3—C4—C9	−136.2 (3)	S1—Cd1—N1—C2	−23.9 (2)
C9—C4—C5—C6	0.8 (7)	N1ⁱ—Cd1—N1—C15	−164.51 (14)
C3—C4—C5—C6	−178.2 (5)	Br1—Cd1—N1—C15	−40.9 (2)
C4—C5—C6—C7	−0.8 (9)	Br2—Cd1—N1—C15	73.3 (2)
C5—C6—C7—C8	0.2 (9)	S1—Cd1—N1—C15	166.6 (2)
C6—C7—C8—C9	0.4 (7)	N1—C2—N2—C10	0.2 (3)
C5—C4—C9—C8	−0.3 (5)	C1—C2—N2—C10	179.7 (2)
C3—C4—C9—C8	178.7 (3)	N1—C2—N2—C3	170.8 (2)
C7—C8—C9—C4	−0.3 (5)	C1—C2—N2—C3	−9.7 (4)
N2—C10—C11—C12	−179.7 (3)	C11—C10—N2—C2	179.8 (3)
C15—C10—C11—C12	0.4 (4)	C15—C10—N2—C2	−0.3 (3)
C10—C11—C12—C13	−1.4 (4)	C11—C10—N2—C3	8.7 (4)
C11—C12—C13—C14	1.2 (5)	C15—C10—N2—C3	−171.4 (2)
C12—C13—C14—C15	0.1 (4)	C4—C3—N2—C2	−100.7 (3)
N2—C10—C15—N1	0.3 (3)	C4—C3—N2—C10	68.5 (3)
C11—C10—C15—N1	−179.8 (2)	O1—C16—N3—C18	0.000 (6)
N2—C10—C15—C14	−179.0 (2)	O1—C16—N3—C17	180.000 (4)
C11—C10—C15—C14	0.9 (4)	C2—C1—S1—C1ⁱ	−128.05 (17)
C13—C14—C15—N1	179.8 (3)	C2—C1—S1—Cd1	−33.2 (2)
C13—C14—C15—C10	−1.1 (4)	N1—Cd1—S1—C1ⁱ	131.08 (12)
N2—C2—N1—C15	0.0 (3)	N1ⁱ—Cd1—S1—C1ⁱ	−27.04 (12)
C1—C2—N1—C15	−179.5 (3)	Br1—Cd1—S1—C1ⁱ	52.02 (10)
N2—C2—N1—Cd1	−171.33 (16)	Br2—Cd1—S1—C1ⁱ	−127.98 (10)
C1—C2—N1—Cd1	9.2 (4)	N1—Cd1—S1—C1	27.03 (12)
C10—C15—N1—C2	−0.2 (3)	N1ⁱ—Cd1—S1—C1	−131.08 (12)
C14—C15—N1—C2	179.0 (3)	Br1—Cd1—S1—C1	−52.02 (10)
C10—C15—N1—Cd1	171.06 (17)	Br2—Cd1—S1—C1	127.98 (10)
C14—C15—N1—Cd1	−9.8 (4)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱⁱ	0.97	2.38	3.004 (5)	122

Symmetry code: (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	[CdBr₂(C₃₀H₂₆N₄S)]·C₃H₇NO
M_r	819.92
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	296
a, b, c (Å)	9.7437 (8), 16.7792 (14), 10.5931 (9)
β (°)	110.029 (1)
V (Å³)	1627.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.23
Crystal size (mm)	0.36 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.390, 0.465
No. of measured, independent and observed [I > 2σ(I)] reflections	9062, 3305, 2742
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.05
No. of reflections	3305
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.64

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.97	2.38	3.004 (5)	121.6

Symmetry code: (i) x, y, z−1.

Acknowledgements

The authors acknowledge financial support and a grant from the Qing Lan Talent Engineering Funds of Lanzhou Jiaotong University.

References

Agh-Atabay, N. M., Baykal, A. & Somer, M. (2004). Transition Met. Chem. 29, 159–163. Web of Science CrossRef CAS Google Scholar
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Dagdigian, J. V. & Reed, C. A. (1979). Inorg. Chem. 18, 2624–2626. CSD CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, H. L., Wang, K. T., Yun, R. R. & Huang, X. C. (2009). Synth. React. Inorg. Met.-Org. Chem. 39, 629–632. CAS Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­bromido[1,1′-di­benzyl-2,2′-(sulfane­diyl­di­methyl­ene)di-1H-benzimidazole]­cadmium(II) di­methyl­formamide solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dibromido[1,1′-dibenzyl-2,2′-(sulfanediyldimethylene)di-1H-benzimidazole]cadmium(II) dimethylformamide solvate