catena-Poly[[(2,2′-dimethyl-4,4′-bi-1,3-thia­zole-κ2N,N′)cadmium]-di-μ-bromido]

Abedi, A.; Rezaei, F.

doi:10.1107/S1600536811020861

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m886

doi:10.1107/S1600536811020861

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catena-Poly[[(2,2′-dimethyl-4,4′-bi-1,3-thiazole-κ²N,N′)cadmium]-di-μ-bromido]

Anita Abedi ^a ^* and Forugh Rezaei ^a

^aDepartment of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: anita_abedi@yahoo.com

(Received 23 May 2011; accepted 31 May 2011; online 11 June 2011)

In the title coordination polymer, [CdBr₂(C₈H₈N₂S₂)]_n, the Cd^II atom is six-coordinated in a distorted octahedral geometry by two N atoms from a 2,2′-dimethyl-4,4′-bi-1,3-thiazole ligand and four bridging Br atoms. The bridging function of the Br atoms leads to a chain structure along [100]. Interchain C—H⋯Br hydrogen bonds and π–π contacts between the thiazole rings [centroid–centroid distances = 3.810 (5) and 3.679 (5) Å] are observed.

Related literature

For metal complexes with 2,2′-dimethyl-4,4′-bi-1,3-thiazole, see: Abedi (2011 ); Abedi & Yahyazade Bali (2010 ); Al-Hashemi et al. (2009 , 2010 ); Khavasi et al. (2008 ); Notash et al. (2008 , 2009 ); Safari et al. (2009 ).

Experimental

Crystal data

[CdBr₂(C₈H₈N₂S₂)]
M_r = 468.51
Triclinic, $[P \overline 1]$
a = 7.1936 (10) Å
b = 9.5775 (11) Å
c = 10.4218 (14) Å
α = 112.714 (9)°
β = 104.149 (11)°
γ = 92.68 (1)°
V = 634.20 (16) Å³
Z = 2
Mo Kα radiation
μ = 8.32 mm⁻¹
T = 298 K
0.28 × 0.18 × 0.13 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.180, T_max = 0.340
7003 measured reflections
3400 independent reflections
2495 reflections with I > 2σ(I)
R_int = 0.160

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.232
S = 1.05
3400 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 2.22 e Å⁻³
Δρ_min = −4.78 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1	2.435 (7)
Cd1—N2	2.372 (7)
Cd1—Br1	2.7112 (11)
Cd1—Br2ⁱ	2.7640 (12)
Cd1—Br1ⁱⁱ	2.8362 (12)
Cd1—Br2	2.7845 (12)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Br1ⁱⁱⁱ	0.93	2.87	3.754 (11)	159
C6—H6⋯Br1ⁱⁱⁱ	0.93	2.86	3.772 (10)	166
C8—H8C⋯Br2	0.96	2.74	3.681 (16)	167
Symmetry code: (iii) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020861/hy2437sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020861/hy2437Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthesis and crystal structures of [HgI₂(dm4bt)] (Abedi & Yahyazade Bali, 2010) and [HgBr₂(dm4bt)] (Abedi, 2011) (dm4bt = 2,2'-dimethyl-4,4'-bi-1,3-thiazole). Dm4bt is a good bidentate ligand, and numerous complexes with dm4bt have been prepared, such as that of zinc (Khavasi et al., 2008), thallium (Notash et al., 2008), cadmium (Notash et al., 2009), mercury (Safari et al., 2009) and copper (Al-Hashemi et al., 2009, 2010). For further investigation of dm4bt, we synthesized the title complex and report herein its crystal structure.

In the title coordination polymer (Fig. 1), the Cd^II atom is six-coordinated in a distorted octahedral geometry by two N atoms from a dm4bt ligand and four bridging Br atoms (Table 1). The bridging function of the bromide atoms leads to a one-dimensional chain structure along [1 0 0] (Fig. 2).

In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the thiazole rings, Cg4···Cg5ⁱ = 3.810 (5) and Cg5···Cg5ⁱⁱ = 3.679 (5) Å [symmetry codes: (i) 1-x, 2-y, 1-z; (ii) -x, 2-y, 1-z. Cg4 and Cg5 are the centroids of the S1/C2/N1/C4/C3 and S2/C6/C5/N2/C7 rings], stabilize the structure.

Related literature top

For metal complexes with 2,2'-dimethyl-4,4'-bi-1,3-thiazole, see: Abedi (2011); Abedi & Yahyazade Bali (2010); Al-Hashemi et al. (2009, 2010); Khavasi et al. (2008); Notash et al. (2008, 2009); Safari et al. (2009).

Experimental top

For the preparation of the title compound, a solution of dm4bt (0.26 g, 1.3 mmol) in methanol (15 ml) was added to a solution of CdBr₂.4H₂O (0.44 g, 1.3 mmol) in methanol (15 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMF. The crystals were isolated after one week (yield: 0.45 g, 73.9%).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Part of the chain structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (a) -x, 1-y, 1-z; (b) 1-x, 1-y, 1-z.]
	Fig. 2. The packing diagram for the title compound.

catena-Poly[[(2,2'-dimethyl-4,4'-bi-1,3-thiazole- κ²N,N')cadmium]-di-µ-bromido] top

Crystal data top

[CdBr₂(C₈H₈N₂S₂)]	Z = 2
M_r = 468.51	F(000) = 440
Triclinic, P1	D_x = 2.454 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1936 (10) Å	Cell parameters from 7003 reflections
b = 9.5775 (11) Å	θ = 2.2–29.2°
c = 10.4218 (14) Å	µ = 8.32 mm⁻¹
α = 112.714 (9)°	T = 298 K
β = 104.149 (11)°	Block, colorless
γ = 92.68 (1)°	0.28 × 0.18 × 0.13 mm
V = 634.20 (16) Å³

Data collection top

Bruker APEX CCD diffractometer	3400 independent reflections
Radiation source: fine-focus sealed tube	2495 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.160
ϕ and ω scans	θ_max = 29.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.180, T_max = 0.340	k = −13→12
7003 measured reflections	l = −14→14

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.232	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.149P)²] where P = (F_o² + 2F_c²)/3
3400 reflections	(Δ/σ)_max = 0.005
136 parameters	Δρ_max = 2.22 e Å⁻³
0 restraints	Δρ_min = −4.78 e Å⁻³

Crystal data top

[CdBr₂(C₈H₈N₂S₂)]	γ = 92.68 (1)°
M_r = 468.51	V = 634.20 (16) Å³
Triclinic, P1	Z = 2
a = 7.1936 (10) Å	Mo Kα radiation
b = 9.5775 (11) Å	µ = 8.32 mm⁻¹
c = 10.4218 (14) Å	T = 298 K
α = 112.714 (9)°	0.28 × 0.18 × 0.13 mm
β = 104.149 (11)°

Data collection top

Bruker APEX CCD diffractometer	3400 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2495 reflections with I > 2σ(I)
T_min = 0.180, T_max = 0.340	R_int = 0.160
7003 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.232	H-atom parameters constrained
S = 1.05	Δρ_max = 2.22 e Å⁻³
3400 reflections	Δρ_min = −4.78 e Å⁻³
136 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.2848 (18)	0.4579 (13)	0.0750 (12)	0.050 (3)
H1A	0.1742	0.3946	0.0710	0.060*
H1B	0.4015	0.4317	0.1221	0.060*
H1C	0.2854	0.4415	−0.0218	0.060*
C2	0.2745 (13)	0.6214 (11)	0.1579 (9)	0.0338 (18)
C3	0.2515 (14)	0.8908 (11)	0.2347 (10)	0.0362 (19)
H3	0.2437	0.9918	0.2478	0.043*
C4	0.2597 (11)	0.8389 (10)	0.3383 (9)	0.0277 (16)
C5	0.2502 (11)	0.9274 (9)	0.4849 (9)	0.0262 (15)
C6	0.2499 (13)	1.0824 (10)	0.5464 (10)	0.0342 (18)
H6	0.2571	1.1478	0.5004	0.041*
C7	0.2327 (13)	0.9521 (11)	0.7021 (10)	0.0332 (18)
C8	0.220 (2)	0.9124 (16)	0.8265 (12)	0.057 (3)
H8C	0.2207	0.8045	0.7987	0.068*
H8B	0.1028	0.9388	0.8511	0.068*
H8A	0.3300	0.9686	0.9089	0.068*
N1	0.2720 (11)	0.6838 (9)	0.2955 (8)	0.0298 (14)
N2	0.2379 (10)	0.8540 (8)	0.5760 (8)	0.0282 (14)
Cd1	0.24677 (9)	0.58678 (7)	0.47579 (7)	0.0302 (2)
Br1	0.36362 (13)	0.31498 (11)	0.34631 (11)	0.0364 (3)
Br2	0.14395 (13)	0.49070 (11)	0.67291 (10)	0.0353 (3)
S1	0.2574 (4)	0.7476 (3)	0.0763 (2)	0.0420 (6)
S2	0.2347 (4)	1.1375 (3)	0.7182 (2)	0.0364 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.056 (6)	0.038 (5)	0.047 (6)	0.009 (5)	0.019 (5)	0.007 (4)
C2	0.034 (4)	0.035 (5)	0.030 (4)	0.007 (4)	0.009 (3)	0.011 (3)
C3	0.041 (5)	0.032 (5)	0.038 (4)	0.009 (4)	0.013 (4)	0.016 (4)
C4	0.023 (4)	0.033 (4)	0.031 (4)	0.010 (3)	0.012 (3)	0.014 (3)
C5	0.022 (4)	0.021 (4)	0.036 (4)	0.005 (3)	0.008 (3)	0.012 (3)
C6	0.035 (5)	0.026 (4)	0.045 (5)	0.007 (3)	0.016 (4)	0.016 (4)
C7	0.032 (4)	0.030 (4)	0.039 (4)	0.007 (3)	0.011 (3)	0.014 (4)
C8	0.084 (9)	0.059 (7)	0.037 (5)	0.032 (7)	0.026 (5)	0.021 (5)
N1	0.031 (4)	0.031 (4)	0.031 (3)	0.004 (3)	0.013 (3)	0.013 (3)
N2	0.025 (3)	0.028 (3)	0.035 (3)	0.011 (3)	0.011 (3)	0.014 (3)
Cd1	0.0309 (4)	0.0278 (4)	0.0387 (4)	0.0106 (2)	0.0152 (3)	0.0168 (3)
Br1	0.0350 (5)	0.0295 (5)	0.0480 (5)	0.0114 (4)	0.0154 (4)	0.0163 (4)
Br2	0.0306 (5)	0.0426 (6)	0.0383 (5)	0.0062 (4)	0.0109 (4)	0.0220 (4)
S1	0.0533 (15)	0.0470 (14)	0.0313 (11)	0.0098 (11)	0.0142 (10)	0.0205 (10)
S2	0.0375 (12)	0.0300 (11)	0.0378 (11)	0.0091 (9)	0.0129 (9)	0.0082 (9)

Geometric parameters (Å, º) top

C1—C2	1.484 (14)	C6—H6	0.9300
C1—H1A	0.9600	C7—N2	1.298 (11)
C1—H1B	0.9600	C7—C8	1.505 (14)
C1—H1C	0.9600	C7—S2	1.717 (10)
C2—N1	1.329 (11)	C8—H8C	0.9600
C2—S1	1.719 (10)	C8—H8B	0.9600
C3—C4	1.343 (13)	C8—H8A	0.9600
C3—S1	1.703 (9)	Cd1—N1	2.435 (7)
C3—H3	0.9300	Cd1—N2	2.372 (7)
C4—N1	1.390 (11)	Cd1—Br1	2.7112 (11)
C4—C5	1.454 (11)	Cd1—Br2ⁱ	2.7640 (12)
C5—C6	1.372 (12)	Cd1—Br1ⁱⁱ	2.8362 (12)
C5—N2	1.397 (11)	Cd1—Br2	2.7845 (12)
C6—S2	1.693 (10)

C2—C1—H1A	109.5	H8C—C8—H8A	109.5
C2—C1—H1B	109.5	H8B—C8—H8A	109.5
H1A—C1—H1B	109.5	C2—N1—C4	110.3 (8)
C2—C1—H1C	109.5	C2—N1—Cd1	135.3 (7)
H1A—C1—H1C	109.5	C4—N1—Cd1	114.0 (5)
H1B—C1—H1C	109.5	C7—N2—C5	110.7 (8)
N1—C2—C1	125.4 (9)	C7—N2—Cd1	134.0 (6)
N1—C2—S1	113.9 (7)	C5—N2—Cd1	115.2 (5)
C1—C2—S1	120.7 (7)	N2—Cd1—N1	71.9 (2)
C4—C3—S1	111.2 (7)	N2—Cd1—Br1	161.12 (17)
C4—C3—H3	124.4	N1—Cd1—Br1	96.12 (18)
S1—C3—H3	124.4	N2—Cd1—Br2ⁱ	94.19 (17)
C3—C4—N1	114.9 (7)	N1—Cd1—Br2ⁱ	84.58 (18)
C3—C4—C5	126.3 (8)	Br1—Cd1—Br2ⁱ	99.26 (4)
N1—C4—C5	118.8 (7)	N2—Cd1—Br2	103.26 (18)
C6—C5—N2	114.2 (8)	N1—Cd1—Br2	168.62 (18)
C6—C5—C4	125.9 (8)	Br1—Cd1—Br2	91.01 (4)
N2—C5—C4	120.0 (7)	Br2ⁱ—Cd1—Br2	85.52 (3)
C5—C6—S2	110.2 (7)	N2—Cd1—Br1ⁱⁱ	82.02 (17)
C5—C6—H6	124.9	N1—Cd1—Br1ⁱⁱ	98.39 (18)
S2—C6—H6	124.9	Br1—Cd1—Br1ⁱⁱ	85.48 (4)
N2—C7—C8	124.8 (9)	Br2ⁱ—Cd1—Br1ⁱⁱ	174.15 (3)
N2—C7—S2	114.6 (7)	Br2—Cd1—Br1ⁱⁱ	90.99 (3)
C8—C7—S2	120.6 (7)	Cd1—Br1—Cd1ⁱⁱ	94.52 (4)
C7—C8—H8C	109.5	Cd1ⁱ—Br2—Cd1	94.48 (3)
C7—C8—H8B	109.5	C3—S1—C2	89.8 (4)
H8C—C8—H8B	109.5	C6—S2—C7	90.3 (4)
C7—C8—H8A	109.5

S1—C3—C4—N1	0.4 (10)	C7—N2—Cd1—Br2	14.8 (8)
S1—C3—C4—C5	−177.4 (7)	C5—N2—Cd1—Br2	−169.0 (5)
C3—C4—C5—C6	−6.7 (14)	C7—N2—Cd1—Br1ⁱⁱ	−74.4 (8)
N1—C4—C5—C6	175.7 (8)	C5—N2—Cd1—Br1ⁱⁱ	101.8 (5)
C3—C4—C5—N2	172.6 (8)	C2—N1—Cd1—N2	−174.0 (9)
N1—C4—C5—N2	−5.1 (11)	C4—N1—Cd1—N2	−2.8 (5)
N2—C5—C6—S2	0.1 (9)	C2—N1—Cd1—Br1	21.0 (9)
C4—C5—C6—S2	179.4 (7)	C4—N1—Cd1—Br1	−167.8 (5)
C1—C2—N1—C4	−179.4 (9)	C2—N1—Cd1—Br2ⁱ	−77.8 (8)
S1—C2—N1—C4	−1.2 (10)	C4—N1—Cd1—Br2ⁱ	93.4 (6)
C1—C2—N1—Cd1	−8.0 (15)	C2—N1—Cd1—Br2	−107.5 (11)
S1—C2—N1—Cd1	170.3 (5)	C4—N1—Cd1—Br2	63.8 (12)
C3—C4—N1—C2	0.5 (11)	C2—N1—Cd1—Br1ⁱⁱ	107.3 (8)
C5—C4—N1—C2	178.5 (7)	C4—N1—Cd1—Br1ⁱⁱ	−81.5 (6)
C3—C4—N1—Cd1	−172.9 (6)	N2—Cd1—Br1—Cd1ⁱⁱ	48.6 (6)
C5—C4—N1—Cd1	5.0 (9)	N1—Cd1—Br1—Cd1ⁱⁱ	97.98 (18)
C8—C7—N2—C5	−179.7 (10)	Br2ⁱ—Cd1—Br1—Cd1ⁱⁱ	−176.54 (3)
S2—C7—N2—C5	1.9 (10)	Br2—Cd1—Br1—Cd1ⁱⁱ	−90.92 (4)
C8—C7—N2—Cd1	−3.4 (15)	Br1ⁱⁱ—Cd1—Br1—Cd1ⁱⁱ	0.0
S2—C7—N2—Cd1	178.2 (4)	N2—Cd1—Br2—Cd1ⁱ	93.26 (18)
C6—C5—N2—C7	−1.3 (10)	N1—Cd1—Br2—Cd1ⁱ	29.7 (9)
C4—C5—N2—C7	179.4 (7)	Br1—Cd1—Br2—Cd1ⁱ	−99.21 (4)
C6—C5—N2—Cd1	−178.4 (6)	Br2ⁱ—Cd1—Br2—Cd1ⁱ	0.0
C4—C5—N2—Cd1	2.3 (9)	Br1ⁱⁱ—Cd1—Br2—Cd1ⁱ	175.30 (3)
C7—N2—Cd1—N1	−176.0 (9)	C4—C3—S1—C2	−0.8 (7)
C5—N2—Cd1—N1	0.2 (5)	N1—C2—S1—C3	1.2 (7)
C7—N2—Cd1—Br1	−123.4 (8)	C1—C2—S1—C3	179.5 (9)
C5—N2—Cd1—Br1	52.8 (9)	C5—C6—S2—C7	0.8 (7)
C7—N2—Cd1—Br2ⁱ	101.1 (8)	N2—C7—S2—C6	−1.6 (8)
C5—N2—Cd1—Br2ⁱ	−82.7 (5)	C8—C7—S2—C6	179.9 (9)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Br1ⁱⁱⁱ	0.93	2.87	3.754 (11)	159
C6—H6···Br1ⁱⁱⁱ	0.93	2.86	3.772 (10)	166
C8—H8C···Br2	0.96	2.74	3.681 (16)	167

Symmetry code: (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[CdBr₂(C₈H₈N₂S₂)]
M_r	468.51
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.1936 (10), 9.5775 (11), 10.4218 (14)
α, β, γ (°)	112.714 (9), 104.149 (11), 92.68 (1)
V (Å³)	634.20 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	8.32
Crystal size (mm)	0.28 × 0.18 × 0.13

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.180, 0.340
No. of measured, independent and observed [I > 2σ(I)] reflections	7003, 3400, 2495
R_int	0.160
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.232, 1.05
No. of reflections	3400
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.22, −4.78

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Cd1—N1	2.435 (7)	Cd1—Br2ⁱ	2.7640 (12)
Cd1—N2	2.372 (7)	Cd1—Br1ⁱⁱ	2.8362 (12)
Cd1—Br1	2.7112 (11)	Cd1—Br2	2.7845 (12)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Br1ⁱⁱⁱ	0.93	2.87	3.754 (11)	159
C6—H6···Br1ⁱⁱⁱ	0.93	2.86	3.772 (10)	166
C8—H8C···Br2	0.96	2.74	3.681 (16)	167

Symmetry code: (iii) x, y+1, z.

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

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