Literature DB >> 21588099

Dichlorido(6,6'-dimethyl-2,2'-bipyridine-κN,N')cadmium(II).

Robabeh Alizadeh, Parisa Mohammadi Eshlaghi, Vahid Amani.

Abstract

In the title compound, [CdCl(2)(C(12)H(12)N(2))], the Cd(II) atom is four-coordinated in a distorted tetra-hedral geometry by two N atoms from a 6,6'-dimethyl-2,2'-bipyridine ligand and two terminal Cl atoms. Inter-molecular C-H⋯Cl hydrogen bonds and π-π stacking inter-actions between the pyridyl rings [centroid-centroid distance = 3.7337 (18) Å] are present in the crystal structure.

Entities: Chemical Disease Species

Year: 2010 PMID： 21588099 PMCID： PMC3007525 DOI： 10.1107/S1600536810029399

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

Related literature

For related structures, see: Alizadeh, Kalateh, Ebadi et al. (2009 ▶); Alizadeh, Kalateh, Khoshtarkib et al. (2009 ▶); Alizadeh, Khoshtarkib et al. (2009 ▶); Itoh et al. (2005 ▶); Kou et al. (2008 ▶); Onggo et al. (2005 ▶).

Experimental

Crystal data

[CdCl2(C12H12N2)] M = 367.55 Monoclinic, a = 7.6715 (9) Å b = 10.0970 (16) Å c = 17.902 (2) Å β = 97.474 (9)° V = 1374.9 (3) Å3 Z = 4 Mo Kα radiation μ = 1.96 mm−1 T = 298 K 0.50 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.569, T max = 0.723 9684 measured reflections 3656 independent reflections 3162 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.086 S = 1.08 3656 reflections 154 parameters H-atom parameters constrained Δρmax = 0.57 e Å−3 Δρmin = −0.63 e Å−3 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 ▶). Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810029399/hy2335sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029399/hy2335Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CdCl₂(C₁₂H₁₂N₂)]	F(000) = 720
M_r = 367.55	D_x = 1.776 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 899 reflections
a = 7.6715 (9) Å	θ = 2.3–29.2°
b = 10.0970 (16) Å	µ = 1.96 mm⁻¹
c = 17.902 (2) Å	T = 298 K
β = 97.474 (9)°	Block, colorless
V = 1374.9 (3) Å³	0.50 × 0.25 × 0.17 mm
Z = 4

Bruker APEX CCD diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	3162 reflections with I > 2σ(I)
graphite	R_int = 0.045
φ and ω scans	θ_max = 29.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.569, T_max = 0.723	k = −11→13
9684 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0364P)² + 0.7364P] where P = (F_o² + 2F_c²)/3
3656 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

	x	y	z	U_iso*/U_eq
C1	0.3527 (5)	0.0531 (4)	0.26805 (18)	0.0737 (9)
H1A	0.4386	0.1215	0.2805	0.088*
H1B	0.2400	0.0927	0.2526	0.088*
H1C	0.3861	0.0002	0.2277	0.088*
C2	0.3427 (4)	−0.0323 (3)	0.33533 (16)	0.0526 (6)
C3	0.3765 (4)	−0.1659 (3)	0.3346 (2)	0.0690 (9)
H3	0.4058	−0.2060	0.2912	0.083*
C4	0.3668 (5)	−0.2393 (3)	0.3977 (3)	0.0754 (11)
H4	0.3912	−0.3296	0.3978	0.090*
C5	0.3202 (4)	−0.1785 (3)	0.4621 (2)	0.0634 (8)
H5	0.3131	−0.2276	0.5055	0.076*
C6	0.2846 (3)	−0.0442 (2)	0.46048 (15)	0.0451 (5)
C7	0.2319 (3)	0.0282 (3)	0.52617 (13)	0.0435 (5)
C8	0.2145 (4)	−0.0343 (3)	0.59409 (17)	0.0613 (8)
H8	0.2401	−0.1239	0.6005	0.074*
C9	0.1589 (5)	0.0381 (4)	0.65159 (17)	0.0698 (9)
H9	0.1458	−0.0026	0.6971	0.084*
C10	0.1233 (4)	0.1690 (4)	0.64177 (16)	0.0638 (8)
H10	0.0852	0.2183	0.6804	0.077*
C11	0.1442 (4)	0.2293 (3)	0.57342 (15)	0.0512 (6)
C12	0.1080 (6)	0.3718 (3)	0.5588 (2)	0.0744 (9)
H12A	0.0164	0.3811	0.5172	0.089*
H12B	0.2127	0.4146	0.5469	0.089*
H12C	0.0715	0.4120	0.6028	0.089*
N1	0.2975 (3)	0.0269 (2)	0.39745 (11)	0.0432 (4)
N2	0.1971 (3)	0.1583 (2)	0.51688 (10)	0.0416 (4)
Cd1	0.23178 (3)	0.245465 (17)	0.402558 (10)	0.04588 (8)
Cl1	0.47640 (12)	0.38850 (9)	0.39295 (5)	0.0758 (2)
Cl2	−0.03250 (11)	0.31365 (9)	0.32689 (4)	0.0646 (2)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.098 (3)	0.074 (2)	0.0528 (16)	0.0060 (19)	0.0223 (16)	−0.0106 (15)
C2	0.0483 (14)	0.0502 (15)	0.0586 (15)	0.0060 (11)	0.0044 (11)	−0.0126 (12)
C3	0.0651 (18)	0.0542 (17)	0.086 (2)	0.0132 (14)	0.0011 (16)	−0.0255 (17)
C4	0.068 (2)	0.0414 (16)	0.112 (3)	0.0141 (13)	−0.006 (2)	−0.0137 (16)
C5	0.0637 (17)	0.0381 (14)	0.084 (2)	0.0048 (12)	−0.0088 (15)	0.0090 (13)
C6	0.0398 (12)	0.0360 (11)	0.0563 (13)	−0.0014 (9)	−0.0060 (10)	0.0041 (10)
C7	0.0396 (11)	0.0452 (13)	0.0438 (12)	−0.0055 (9)	−0.0017 (9)	0.0094 (10)
C8	0.0597 (16)	0.0636 (18)	0.0590 (16)	−0.0095 (14)	0.0019 (13)	0.0260 (14)
C9	0.0691 (19)	0.096 (3)	0.0444 (14)	−0.0182 (18)	0.0075 (13)	0.0219 (16)
C10	0.0610 (17)	0.092 (3)	0.0399 (13)	−0.0105 (16)	0.0103 (11)	−0.0033 (14)
C11	0.0536 (14)	0.0589 (16)	0.0417 (12)	−0.0037 (12)	0.0078 (10)	−0.0053 (11)
C12	0.106 (3)	0.0579 (19)	0.0631 (18)	0.0082 (18)	0.0232 (18)	−0.0126 (15)
N1	0.0445 (10)	0.0377 (10)	0.0469 (10)	0.0011 (8)	0.0041 (8)	−0.0034 (8)
N2	0.0452 (10)	0.0430 (10)	0.0363 (9)	−0.0023 (8)	0.0040 (7)	0.0022 (8)
Cd1	0.05923 (13)	0.03760 (12)	0.04198 (11)	0.00404 (7)	0.01099 (8)	0.00679 (6)
Cl1	0.0785 (5)	0.0607 (5)	0.0887 (6)	−0.0146 (4)	0.0127 (4)	0.0244 (4)
Cl2	0.0668 (4)	0.0701 (5)	0.0562 (4)	0.0142 (4)	0.0048 (3)	0.0153 (3)

C1—C2	1.491 (5)	C8—C9	1.374 (5)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.357 (6)
C1—H1C	0.9600	C9—H9	0.9300
C2—N1	1.347 (3)	C10—C11	1.394 (4)
C2—C3	1.374 (4)	C10—H10	0.9300
C3—C4	1.361 (6)	C11—N2	1.346 (3)
C3—H3	0.9300	C11—C12	1.482 (4)
C4—C5	1.394 (6)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.383 (4)	C12—H12C	0.9600
C5—H5	0.9300	Cd1—N1	2.268 (2)
C6—N1	1.352 (3)	Cd1—N2	2.2752 (19)
C6—C7	1.485 (4)	Cd1—Cl1	2.3919 (9)
C7—N2	1.345 (3)	Cd1—Cl2	2.3885 (8)
C7—C8	1.392 (3)

C2—C1—H1A	109.5	C10—C9—C8	119.9 (3)
C2—C1—H1B	109.5	C10—C9—H9	120.1
H1A—C1—H1B	109.5	C8—C9—H9	120.1
C2—C1—H1C	109.5	C9—C10—C11	119.7 (3)
H1A—C1—H1C	109.5	C9—C10—H10	120.2
H1B—C1—H1C	109.5	C11—C10—H10	120.2
N1—C2—C3	120.8 (3)	N2—C11—C10	120.5 (3)
N1—C2—C1	117.1 (3)	N2—C11—C12	116.9 (3)
C3—C2—C1	122.0 (3)	C10—C11—C12	122.6 (3)
C4—C3—C2	119.8 (3)	C11—C12—H12A	109.5
C4—C3—H3	120.1	C11—C12—H12B	109.5
C2—C3—H3	120.1	H12A—C12—H12B	109.5
C3—C4—C5	119.6 (3)	C11—C12—H12C	109.5
C3—C4—H4	120.2	H12A—C12—H12C	109.5
C5—C4—H4	120.2	H12B—C12—H12C	109.5
C6—C5—C4	119.1 (3)	C2—N1—C6	120.6 (2)
C6—C5—H5	120.5	C2—N1—Cd1	123.18 (18)
C4—C5—H5	120.5	C6—N1—Cd1	116.24 (16)
N1—C6—C5	120.1 (3)	C7—N2—C11	120.1 (2)
N1—C6—C7	117.2 (2)	C7—N2—Cd1	116.38 (16)
C5—C6—C7	122.7 (3)	C11—N2—Cd1	123.52 (18)
N2—C7—C8	120.7 (3)	N1—Cd1—N2	73.28 (8)
N2—C7—C6	116.9 (2)	N1—Cd1—Cl2	115.75 (6)
C8—C7—C6	122.4 (3)	N2—Cd1—Cl2	115.59 (6)
C9—C8—C7	119.2 (3)	N1—Cd1—Cl1	113.82 (6)
C9—C8—H8	120.4	N2—Cd1—Cl1	118.88 (6)
C7—C8—H8	120.4	Cl2—Cd1—Cl1	113.65 (3)

N1—C2—C3—C4	−1.0 (5)	C5—C6—N1—Cd1	179.2 (2)
C1—C2—C3—C4	179.5 (3)	C7—C6—N1—Cd1	−1.0 (3)
C2—C3—C4—C5	1.0 (5)	C8—C7—N2—C11	−0.3 (4)
C3—C4—C5—C6	0.0 (5)	C6—C7—N2—C11	178.2 (2)
C4—C5—C6—N1	−1.0 (4)	C8—C7—N2—Cd1	−179.97 (19)
C4—C5—C6—C7	179.2 (3)	C6—C7—N2—Cd1	−1.4 (3)
N1—C6—C7—N2	1.6 (3)	C10—C11—N2—C7	−0.5 (4)
C5—C6—C7—N2	−178.6 (2)	C12—C11—N2—C7	−179.8 (3)
N1—C6—C7—C8	−179.9 (2)	C10—C11—N2—Cd1	179.1 (2)
C5—C6—C7—C8	−0.1 (4)	C12—C11—N2—Cd1	−0.2 (4)
N2—C7—C8—C9	0.9 (4)	C2—N1—Cd1—N2	178.4 (2)
C6—C7—C8—C9	−177.6 (3)	C6—N1—Cd1—N2	0.18 (16)
C7—C8—C9—C10	−0.5 (5)	C2—N1—Cd1—Cl2	67.6 (2)
C8—C9—C10—C11	−0.3 (5)	C6—N1—Cd1—Cl2	−110.67 (16)
C9—C10—C11—N2	0.8 (5)	C2—N1—Cd1—Cl1	−66.8 (2)
C9—C10—C11—C12	−179.9 (3)	C6—N1—Cd1—Cl1	114.92 (16)
C3—C2—N1—C6	0.1 (4)	C7—N2—Cd1—N1	0.69 (16)
C1—C2—N1—C6	179.5 (3)	C11—N2—Cd1—N1	−179.0 (2)
C3—C2—N1—Cd1	−178.1 (2)	C7—N2—Cd1—Cl2	111.73 (16)
C1—C2—N1—Cd1	1.4 (4)	C11—N2—Cd1—Cl2	−67.9 (2)
C5—C6—N1—C2	0.9 (4)	C7—N2—Cd1—Cl1	−107.72 (16)
C7—C6—N1—C2	−179.3 (2)	C11—N2—Cd1—Cl1	72.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cl1ⁱ	0.96	2.76	3.711 (4)	169
C5—H5···Cl1ⁱⁱ	0.93	2.79	3.551 (3)	140

Table 1

Selected bond lengths (Å)

Cd1—N1	2.268 (2)
Cd1—N2	2.2752 (19)
Cd1—Cl1	2.3919 (9)
Cd1—Cl2	2.3885 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Cl1ⁱ	0.96	2.76	3.711 (4)	169
C5—H5⋯Cl1ⁱⁱ	0.93	2.79	3.551 (3)	140

Symmetry codes: (i) ; (ii) .

5 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. Syntheses, structural analyses and redox kinetics of four-coordinate [CuL2]2+ and five-coordinate [CuL2(solvent)]2+ complexes (L = 6,6'-dimethyl-2,2'-bipyridine or 2,9-dimethyl-1,10-phenanthroline): completely gated reduction reaction of [Cu(dmp)2]2+ in nitromethane.

Authors: Sumitaka Itoh; Nobuyuki Kishikawa; Takayoshi Suzuki; Hideo D Takagi
Journal: Dalton Trans Date: 2005-02-16 Impact factor: 4.390

3. 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

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

Authors: Robabeh Alizadeh; Khadijeh Kalateh; Amin Ebadi; Roya Ahmadi; Vahid Amani
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-26

5. (6,6'-Dimethyl-2,2'-bipyridine-κN,N')diiodidozinc(II).

Authors: Robabeh Alizadeh; Khadijeh Kalateh; Zeinab Khoshtarkib; Roya Ahmadi; Vahid Amani
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-28