Literature DB >> 21587391

Dibromido(6-methyl-2,2'-bipyridine-κN,N')zinc(II).

Khadijeh Kalateh¹, Roya Ahmadi, Vahid Amani.

Abstract

In the title compound, [ZnBr(2)(C(11)n class="Species">H(10)N(2))], the Zn(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from a 6-methyl-2,2'-bipyridine ligand and two terminal Br atoms. Weak inter-molecular C-H⋯Br hydrogen bonds and π-π stacking inter-actions between the pyridine rings [centroid-centroid distances = 3.763 (5) and 3.835 (6) Å] contribute to crystal-packing effects.

Entities: Chemical Disease Species

Year: 2010 PMID： 21587391 PMCID： PMC2983320 DOI： 10.1107/S1600536810035658

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For unusual coordination geometries on transition metal atoms, see: Beeston et al. (1998 ▶), Meyer et al. (1999 ▶); For related literature, see: Ahmadi et al. (2009 ▶); Ahmadi, Ebadi et al. (2008 ▶); Ahmadi, Kalateh et al. (2008 ▶); Alizadeh et al. (2009 ▶); Amani et al. (2009 ▶); Newkome et al. (1982 ▶); Onggo et al. (1990 ▶, 2005 ▶).

Experimental

Crystal data

[ZnBr2(C11n class="Species">H10N2)] M = 395.40 Monoclinic, a = 7.6445 (7) Å b = 9.7487 (11) Å c = 17.8347 (18) Å β = 96.972 (8)° V = 1319.3 (2) Å3 Z = 4 Mo Kα radiation μ = 7.89 mm−1 T = 298 K 0.46 × 0.30 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.076, T max = 0.310 15389 measured reflections 3567 independent reflections 2498 reflections with I > 2σ(I) R int = 0.119

Refinement

R[F 2 > 2σ(F 2)] = 0.086 wR(F 2) = 0.207 S = 1.13 3567 reflections 145 parameters H-atom parameters constrained Δρmax = 2.14 e Å−3 Δρmin = −1.14 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (n class="Chemical">Bruker, 1998 ▶); 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035658/jj2041sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035658/jj2041Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnBr₂(C₁₁H₁₀N₂)]	F(000) = 760
M_r = 395.40	D_x = 1.991 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 985 reflections
a = 7.6445 (7) Å	θ = 2.3–29.4°
b = 9.7487 (11) Å	µ = 7.89 mm⁻¹
c = 17.8347 (18) Å	T = 298 K
β = 96.972 (8)°	Prism, colorless
V = 1319.3 (2) Å³	0.46 × 0.30 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	2498 reflections with I > 2σ(I)
graphite	R_int = 0.119
φ and ω scans	θ_max = 29.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→10
T_min = 0.076, T_max = 0.310	k = −13→13
15389 measured reflections	l = −24→24

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0565P)² + 8.4252P] where P = (F_o² + 2F_c²)/3
3567 reflections	(Δ/σ)_max = 0.002
145 parameters	Δρ_max = 2.14 e Å⁻³
0 restraints	Δρ_min = −1.14 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	U_iso*/U_eq
C1	0.651 (2)	0.9482 (15)	0.2106 (6)	0.099 (5)
H1A	0.7590	0.9042	0.2302	0.119*
H1B	0.5594	0.8805	0.2012	0.119*
H1C	0.6183	1.0135	0.2468	0.119*
C2	0.6740 (14)	1.0200 (10)	0.1390 (6)	0.063 (2)
C3	0.6519 (15)	1.1604 (12)	0.1292 (7)	0.074 (3)
H3	0.6227	1.2153	0.1685	0.089*
C4	0.6738 (15)	1.2162 (11)	0.0608 (8)	0.075 (3)
H4	0.6559	1.3097	0.0527	0.090*
C5	0.7221 (13)	1.1355 (10)	0.0041 (6)	0.063 (2)
H5	0.7415	1.1739	−0.0419	0.076*
C6	0.7415 (11)	0.9971 (9)	0.0160 (5)	0.051 (2)
C7	0.7873 (11)	0.8977 (10)	−0.0412 (5)	0.0509 (19)
C8	0.8184 (14)	0.9373 (12)	−0.1129 (6)	0.070 (3)
H8	0.8168	1.0293	−0.1268	0.084*
C9	0.8523 (16)	0.8339 (15)	−0.1639 (6)	0.080 (3)
H9	0.8735	0.8568	−0.2126	0.096*
C10	0.8542 (18)	0.7025 (14)	−0.1426 (6)	0.080 (3)
H10	0.8736	0.6339	−0.1768	0.097*
C11	0.8280 (15)	0.6692 (12)	−0.0710 (6)	0.072 (3)
H11	0.8344	0.5776	−0.0563	0.087*
N1	0.7182 (10)	0.9406 (7)	0.0849 (4)	0.0508 (17)
N2	0.7930 (10)	0.7647 (8)	−0.0208 (4)	0.0530 (17)
Br1	1.04853 (15)	0.69883 (13)	0.15998 (7)	0.0756 (4)
Br2	0.54078 (15)	0.58954 (13)	0.11809 (7)	0.0767 (4)
Zn1	0.76827 (14)	0.73342 (11)	0.09099 (6)	0.0525 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.147 (13)	0.102 (10)	0.056 (6)	0.016 (9)	0.040 (8)	−0.011 (6)
C2	0.063 (6)	0.057 (5)	0.068 (6)	0.004 (5)	0.010 (5)	−0.004 (5)
C3	0.061 (6)	0.070 (7)	0.088 (8)	0.006 (5)	0.001 (5)	−0.018 (6)
C4	0.071 (7)	0.051 (5)	0.102 (9)	0.003 (5)	0.005 (6)	0.013 (6)
C5	0.063 (6)	0.056 (5)	0.070 (6)	0.003 (5)	0.008 (5)	0.015 (5)
C6	0.038 (4)	0.058 (5)	0.056 (5)	−0.005 (4)	−0.001 (3)	0.021 (4)
C7	0.045 (4)	0.063 (5)	0.043 (4)	−0.006 (4)	0.002 (3)	0.009 (4)
C8	0.060 (6)	0.089 (7)	0.058 (6)	−0.018 (5)	0.002 (5)	0.028 (5)
C9	0.076 (7)	0.122 (11)	0.046 (5)	−0.016 (7)	0.018 (5)	−0.005 (6)
C10	0.091 (8)	0.098 (9)	0.056 (6)	−0.006 (7)	0.021 (6)	−0.010 (6)
C11	0.081 (7)	0.073 (7)	0.068 (6)	0.007 (6)	0.029 (6)	−0.004 (5)
N1	0.052 (4)	0.050 (4)	0.052 (4)	0.004 (3)	0.015 (3)	0.008 (3)
N2	0.059 (4)	0.059 (4)	0.042 (3)	−0.001 (4)	0.012 (3)	0.008 (3)
Br1	0.0576 (6)	0.0870 (8)	0.0815 (7)	0.0001 (5)	0.0052 (5)	0.0382 (6)
Br2	0.0673 (7)	0.0768 (7)	0.0878 (8)	−0.0131 (5)	0.0173 (6)	0.0197 (6)
Zn1	0.0560 (6)	0.0509 (6)	0.0528 (6)	0.0038 (5)	0.0149 (4)	0.0129 (4)

C1—C2	1.486 (16)	C7—N2	1.346 (11)
C1—H1A	0.9600	C7—C8	1.383 (12)
C1—H1B	0.9600	C8—C9	1.402 (17)
C1—H1C	0.9600	C8—H8	0.9300
C2—N1	1.312 (12)	C9—C10	1.335 (18)
C2—C3	1.388 (15)	C9—H9	0.9300
C3—C4	1.364 (17)	C10—C11	1.355 (15)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.368 (16)	C11—N2	1.342 (13)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.370 (13)	N1—Zn1	2.057 (7)
C5—H5	0.9300	N2—Zn1	2.048 (7)
C6—N1	1.378 (10)	Br1—Zn1	2.3617 (16)
C6—C7	1.480 (13)	Br2—Zn1	2.3300 (15)

Cg1···Cg2ⁱ	3.762 (5)	Cg2···Cg3ⁱⁱ	3.835 (6)

C2—C1—H1A	109.5	C7—C8—C9	117.7 (10)
C2—C1—H1B	109.5	C7—C8—H8	121.2
H1A—C1—H1B	109.5	C9—C8—H8	121.2
C2—C1—H1C	109.5	C10—C9—C8	120.1 (10)
H1A—C1—H1C	109.5	C10—C9—H9	120.0
H1B—C1—H1C	109.5	C8—C9—H9	120.0
N1—C2—C3	121.8 (10)	C9—C10—C11	120.0 (11)
N1—C2—C1	115.0 (9)	C9—C10—H10	120.0
C3—C2—C1	123.2 (10)	C11—C10—H10	120.0
C4—C3—C2	118.7 (11)	N2—C11—C10	121.8 (11)
C4—C3—H3	120.7	N2—C11—H11	119.1
C2—C3—H3	120.7	C10—C11—H11	119.1
C3—C4—C5	120.3 (10)	C2—N1—C6	119.5 (8)
C3—C4—H4	119.8	C2—N1—Zn1	127.1 (6)
C5—C4—H4	119.8	C6—N1—Zn1	113.3 (6)
C4—C5—C6	119.1 (10)	C11—N2—C7	119.4 (8)
C4—C5—H5	120.5	C11—N2—Zn1	126.6 (7)
C6—C5—H5	120.5	C7—N2—Zn1	113.8 (6)
C5—C6—N1	120.5 (9)	N2—Zn1—N1	80.9 (3)
C5—C6—C7	124.6 (8)	N2—Zn1—Br2	116.8 (2)
N1—C6—C7	114.9 (8)	N1—Zn1—Br2	117.6 (2)
N2—C7—C8	121.0 (9)	N2—Zn1—Br1	110.1 (2)
N2—C7—C6	116.5 (7)	N1—Zn1—Br1	108.6 (2)
C8—C7—C6	122.4 (9)	Br2—Zn1—Br1	117.30 (6)

N1—C2—C3—C4	1.2 (17)	C5—C6—N1—Zn1	−176.7 (7)
C1—C2—C3—C4	−179.0 (12)	C7—C6—N1—Zn1	3.4 (9)
C2—C3—C4—C5	−2.1 (18)	C10—C11—N2—C7	−1.4 (17)
C3—C4—C5—C6	2.5 (17)	C10—C11—N2—Zn1	−175.1 (9)
C4—C5—C6—N1	−2.0 (15)	C8—C7—N2—C11	−0.5 (14)
C4—C5—C6—C7	177.9 (9)	C6—C7—N2—C11	177.8 (9)
C5—C6—C7—N2	−177.1 (9)	C8—C7—N2—Zn1	174.0 (7)
N1—C6—C7—N2	2.9 (11)	C6—C7—N2—Zn1	−7.7 (10)
C5—C6—C7—C8	1.2 (14)	C11—N2—Zn1—N1	−178.6 (9)
N1—C6—C7—C8	−178.8 (8)	C7—N2—Zn1—N1	7.4 (6)
N2—C7—C8—C9	1.3 (15)	C11—N2—Zn1—Br2	−62.2 (9)
C6—C7—C8—C9	−176.9 (9)	C7—N2—Zn1—Br2	123.7 (6)
C7—C8—C9—C10	−0.1 (17)	C11—N2—Zn1—Br1	74.8 (9)
C8—C9—C10—C11	−2(2)	C7—N2—Zn1—Br1	−99.2 (6)
C9—C10—C11—N2	3(2)	C2—N1—Zn1—N2	176.6 (9)
C3—C2—N1—C6	−0.8 (15)	C6—N1—Zn1—N2	−5.8 (6)
C1—C2—N1—C6	179.5 (10)	C2—N1—Zn1—Br2	61.0 (9)
C3—C2—N1—Zn1	176.7 (8)	C6—N1—Zn1—Br2	−121.3 (5)
C1—C2—N1—Zn1	−3.0 (14)	C2—N1—Zn1—Br1	−75.2 (8)
C5—C6—N1—C2	1.2 (13)	C6—N1—Zn1—Br1	102.5 (6)
C7—C6—N1—C2	−178.7 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Br1ⁱⁱⁱ	0.96	2.86	3.805 (14)	169
C8—H8···Br1ⁱⁱ	0.93	2.93	3.812 (12)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Br1ⁱ	0.96	2.86	3.805 (14)	169
C8—H8⋯Br1ⁱⁱ	0.93	2.93	3.812 (12)	159

Symmetry codes: (i) ; (ii) .

6 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis, Characterization, and Photochemical/Photophysical Properties of Ruthenium(II) Complexes with Hexadentate Bipyridine and Phenanthroline Ligands.

Authors: Ruth F. Beeston; W. Stephen Aldridge; Joseph A. Treadway; Michael C. Fitzgerald; Benjamin A. DeGraff; Shannon E. Stitzel
Journal: Inorg Chem Date: 1998-08-24 Impact factor: 5.165

3. Tetra-kis(6-methyl-2,2'-bipyridine)-1κN,N';2κN,N';3κN,N';4κN,N'-tetra-μ-nitrato-1:2κO:O';2:3κO:O',O'';2:3κO,O':O'';3:4κO:O'-tetra-nitrato-1κO,O';4κO,O'-tetra-lead(II).

Authors: Roya Ahmadi; Khadijeh Kalateh; Robabeh Alizadeh; Zeinab Khoshtarkib; Vahid Amani
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-05

4. Dibromido(6,6'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).

Authors: Robabeh Alizadeh; Zeinab Khoshtarkib; Katayoon Chegeni; Amin Ebadi; Vahid Amani
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-07

5. Dichlorido(6-methyl-2,2'-bipyridine-κN,N')mercury(II).

Authors: Roya Ahmadi; Amin Ebadi; Khadijeh Kalateh; Ali Norouzi; Vahid Amani
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-10-15

6. Dichlorido(6-methyl-2,2'-bipyridine-κN,N')zinc(II).

Authors: Roya Ahmadi; Khadijeh Kalateh; Amin Ebadi; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-09-13