Literature DB >> 21203070

Dibromido[N-propyl-N'-(2-pyridylmethyl-idene)ethane-1,2-diamine]zinc(II).

Abstract

The title complex, [ZnBr(2)(C(11)H(17)N(3))], is a mononuclear zinc(II) compound derived from the Schiff base N-propyl-N'-(1-pyridin-2-ylmethyl-idene)ethane-1,2-diamine. The Zn(II) atom is five-coordinate, binding to the imine N, pyridine N, and amine N atoms of the Schiff base ligand and to two bromide anions in a distorted trigonal-bipyramidal coordination geometry. Adjacent mol-ecules are linked through inter-molecular N-H⋯Br hydrogen bonds, forming dimers.

Entities: Chemical Disease Gene Species

Year: 2008 PMID： 21203070 PMCID： PMC2962000 DOI： 10.1107/S1600536808023660

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

Related literature

For background to the chemistry of Schiff base complexes, see: Ali et al. (2008 ▶); Biswas et al. (2008 ▶); Chen et al. (2008 ▶); Darensbourg & Frantz (2007 ▶); Habibi et al. (2007 ▶); Kawamoto et al. (2008 ▶); Lipscomb & Sträter (1996 ▶); Tomat et al. (2007 ▶); Wu et al. (2008 ▶); Yuan et al. (2007 ▶). For related structures, see: Dapporto et al. (2001 ▶); You & Zhu (2006 ▶).

Experimental

Crystal data

[ZnBr2(C11H17N3)] M = 416.47 Monoclinic, a = 8.252 (4) Å b = 12.249 (5) Å c = 14.726 (6) Å β = 94.562 (7)° V = 1483.8 (11) Å3 Z = 4 Mo Kα radiation μ = 7.02 mm−1 T = 298 (2) K 0.32 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.212, T max = 0.227 (expected range = 0.114–0.122) 12333 measured reflections 3378 independent reflections 2167 reflections with I > 2σ(I) R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.105 S = 1.01 3378 reflections 159 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.91 e Å−3 Δρmin = −0.80 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023660/sj2523sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023660/sj2523Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnBr₂(C₁₁H₁₇N₃)]	F₀₀₀ = 816
M_r = 416.47	D_x = 1.864 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1994 reflections
a = 8.252 (4) Å	θ = 2.2–25.3º
b = 12.249 (5) Å	µ = 7.02 mm⁻¹
c = 14.726 (6) Å	T = 298 (2) K
β = 94.562 (7)º	Block, colorless
V = 1483.8 (11) Å³	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3378 independent reflections
Radiation source: fine-focus sealed tube	2167 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.083
T = 298(2) K	θ_max = 27.5º
ω scans	θ_min = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.212, T_max = 0.227	k = −15→15
12333 measured reflections	l = −18→19

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0211P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3378 reflections	Δρ_max = 0.91 e Å⁻³
159 parameters	Δρ_min = −0.80 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0140 (7)

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
Zn1	0.04170 (7)	0.30316 (4)	0.86078 (4)	0.02971 (19)
Br1	−0.19476 (6)	0.34399 (5)	0.94074 (4)	0.0454 (2)
Br2	0.00560 (8)	0.29983 (5)	0.69779 (4)	0.0524 (2)
N1	0.0385 (5)	0.1154 (3)	0.8679 (3)	0.0359 (10)
N2	0.2385 (5)	0.2563 (3)	0.9510 (3)	0.0338 (10)
N3	0.1741 (5)	0.4581 (3)	0.8836 (3)	0.0296 (9)
C1	0.1561 (6)	0.0745 (4)	0.9254 (3)	0.0351 (12)
C2	0.1774 (8)	−0.0353 (4)	0.9398 (4)	0.0495 (15)
H2	0.2599	−0.0611	0.9810	0.059*
C3	0.0742 (9)	−0.1061 (5)	0.8922 (5)	0.0606 (18)
H3	0.0849	−0.1811	0.9009	0.073*
C4	−0.0449 (8)	−0.0652 (5)	0.8318 (5)	0.0575 (17)
H4	−0.1150	−0.1117	0.7978	0.069*
C5	−0.0591 (7)	0.0466 (5)	0.8222 (4)	0.0489 (15)
H5	−0.1412	0.0743	0.7818	0.059*
C6	0.2635 (6)	0.1575 (4)	0.9712 (4)	0.0367 (12)
H6	0.3474	0.1373	1.0138	0.044*
C7	0.3456 (6)	0.3442 (4)	0.9865 (4)	0.0396 (13)
H7A	0.4553	0.3172	1.0003	0.048*
H7B	0.3068	0.3745	1.0417	0.048*
C8	0.3422 (6)	0.4295 (4)	0.9126 (4)	0.0375 (13)
H8A	0.4004	0.4941	0.9352	0.045*
H8B	0.3958	0.4016	0.8611	0.045*
C9	0.1638 (6)	0.5399 (4)	0.8098 (4)	0.0400 (13)
H9A	0.1939	0.5061	0.7540	0.048*
H9B	0.2404	0.5984	0.8252	0.048*
C10	−0.0046 (6)	0.5869 (4)	0.7943 (4)	0.0426 (14)
H10A	−0.0825	0.5278	0.7857	0.051*
H10B	−0.0298	0.6277	0.8478	0.051*
C11	−0.0207 (7)	0.6607 (5)	0.7126 (4)	0.0641 (19)
H11A	0.0663	0.7129	0.7167	0.096*
H11B	−0.1230	0.6983	0.7108	0.096*
H11C	−0.0158	0.6180	0.6582	0.096*
H3A	0.130 (7)	0.491 (4)	0.930 (3)	0.080*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0321 (3)	0.0296 (3)	0.0266 (3)	0.0004 (2)	−0.0029 (2)	−0.0032 (3)
Br1	0.0399 (3)	0.0451 (4)	0.0526 (4)	−0.0043 (2)	0.0125 (3)	−0.0179 (3)
Br2	0.0811 (5)	0.0481 (4)	0.0263 (3)	0.0018 (3)	−0.0070 (3)	−0.0066 (3)
N1	0.043 (3)	0.033 (2)	0.031 (3)	−0.003 (2)	0.002 (2)	−0.001 (2)
N2	0.039 (3)	0.032 (2)	0.029 (2)	0.000 (2)	−0.003 (2)	0.001 (2)
N3	0.036 (2)	0.027 (2)	0.026 (2)	−0.0041 (17)	0.0009 (19)	−0.0019 (18)
C1	0.046 (3)	0.031 (3)	0.029 (3)	0.002 (2)	0.010 (2)	0.005 (2)
C2	0.065 (4)	0.035 (3)	0.050 (4)	0.007 (3)	0.013 (3)	0.009 (3)
C3	0.087 (5)	0.028 (3)	0.071 (5)	0.002 (3)	0.032 (4)	0.004 (3)
C4	0.070 (4)	0.037 (4)	0.067 (5)	−0.010 (3)	0.019 (4)	−0.010 (3)
C5	0.044 (3)	0.047 (4)	0.056 (4)	−0.006 (3)	0.000 (3)	−0.011 (3)
C6	0.041 (3)	0.038 (3)	0.030 (3)	0.008 (2)	−0.002 (2)	0.000 (2)
C7	0.042 (3)	0.040 (3)	0.035 (3)	−0.001 (2)	−0.011 (3)	−0.002 (3)
C8	0.037 (3)	0.033 (3)	0.041 (3)	−0.008 (2)	−0.002 (2)	−0.003 (3)
C9	0.046 (3)	0.033 (3)	0.041 (3)	−0.009 (2)	0.005 (3)	0.004 (3)
C10	0.044 (3)	0.032 (3)	0.052 (4)	0.002 (2)	0.003 (3)	0.007 (3)
C11	0.065 (4)	0.054 (4)	0.071 (5)	0.004 (3)	−0.004 (4)	0.030 (3)

Zn1—N2	2.095 (4)	C4—C5	1.380 (8)
Zn1—N3	2.202 (4)	C4—H4	0.9300
Zn1—N1	2.303 (4)	C5—H5	0.9300
Zn1—Br2	2.3954 (13)	C6—H6	0.9300
Zn1—Br1	2.4102 (11)	C7—C8	1.508 (7)
N1—C5	1.313 (6)	C7—H7A	0.9700
N1—C1	1.334 (6)	C7—H7B	0.9700
N2—C6	1.259 (6)	C8—H8A	0.9700
N2—C7	1.463 (6)	C8—H8B	0.9700
N3—C8	1.461 (6)	C9—C10	1.505 (7)
N3—C9	1.477 (6)	C9—H9A	0.9700
N3—H3A	0.90 (5)	C9—H9B	0.9700
C1—C2	1.371 (7)	C10—C11	1.501 (7)
C1—C6	1.475 (7)	C10—H10A	0.9700
C2—C3	1.369 (8)	C10—H10B	0.9700
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.367 (8)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600

N2—Zn1—N3	77.83 (16)	N1—C5—H5	118.7
N2—Zn1—N1	73.04 (15)	C4—C5—H5	118.7
N3—Zn1—N1	149.43 (15)	N2—C6—C1	118.2 (5)
N2—Zn1—Br2	131.24 (11)	N2—C6—H6	120.9
N3—Zn1—Br2	100.86 (11)	C1—C6—H6	120.9
N1—Zn1—Br2	91.57 (11)	N2—C7—C8	106.0 (4)
N2—Zn1—Br1	111.33 (12)	N2—C7—H7A	110.5
N3—Zn1—Br1	99.08 (11)	C8—C7—H7A	110.5
N1—Zn1—Br1	99.94 (11)	N2—C7—H7B	110.5
Br2—Zn1—Br1	116.88 (4)	C8—C7—H7B	110.5
C5—N1—C1	118.1 (5)	H7A—C7—H7B	108.7
C5—N1—Zn1	128.8 (4)	N3—C8—C7	109.8 (4)
C1—N1—Zn1	113.1 (3)	N3—C8—H8A	109.7
C6—N2—C7	122.7 (4)	C7—C8—H8A	109.7
C6—N2—Zn1	121.2 (3)	N3—C8—H8B	109.7
C7—N2—Zn1	116.1 (3)	C7—C8—H8B	109.7
C8—N3—C9	112.0 (4)	H8A—C8—H8B	108.2
C8—N3—Zn1	106.6 (3)	N3—C9—C10	111.7 (4)
C9—N3—Zn1	118.3 (3)	N3—C9—H9A	109.3
C8—N3—H3A	109 (4)	C10—C9—H9A	109.3
C9—N3—H3A	105 (4)	N3—C9—H9B	109.3
Zn1—N3—H3A	106 (4)	C10—C9—H9B	109.3
N1—C1—C2	122.9 (5)	H9A—C9—H9B	107.9
N1—C1—C6	114.3 (4)	C11—C10—C9	111.9 (5)
C2—C1—C6	122.7 (5)	C11—C10—H10A	109.2
C3—C2—C1	118.4 (6)	C9—C10—H10A	109.2
C3—C2—H2	120.8	C11—C10—H10B	109.2
C1—C2—H2	120.8	C9—C10—H10B	109.2
C4—C3—C2	119.1 (6)	H10A—C10—H10B	107.9
C4—C3—H3	120.5	C10—C11—H11A	109.5
C2—C3—H3	120.5	C10—C11—H11B	109.5
C3—C4—C5	118.8 (6)	H11A—C11—H11B	109.5
C3—C4—H4	120.6	C10—C11—H11C	109.5
C5—C4—H4	120.6	H11A—C11—H11C	109.5
N1—C5—C4	122.7 (6)	H11B—C11—H11C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Br1ⁱ	0.90 (5)	2.80 (4)	3.539 (4)	141 (5)

Zn1—N2	2.095 (4)
Zn1—N3	2.202 (4)
Zn1—N1	2.303 (4)
Zn1—Br2	2.3954 (13)
Zn1—Br1	2.4102 (11)

N2—Zn1—N3	77.83 (16)
N2—Zn1—N1	73.04 (15)
N3—Zn1—N1	149.43 (15)
N2—Zn1—Br2	131.24 (11)
N3—Zn1—Br2	100.86 (11)
N1—Zn1—Br2	91.57 (11)
N2—Zn1—Br1	111.33 (12)
N3—Zn1—Br1	99.08 (11)
N1—Zn1—Br1	99.94 (11)
Br2—Zn1—Br1	116.88 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Br1ⁱ	0.90 (5)	2.80 (4)	3.539 (4)	141 (5)

Symmetry code: (i) .

11 in total

1. Recent Advances in Zinc Enzymology.

Authors: William N. Lipscomb; Norbert Sträter
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2. A short history of SHELX.

Authors: George M Sheldrick
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3. Stabilization of a helical water chain in a metal-organic host of a trinuclear Schiff base complex.

Authors: Chaitali Biswas; Michael G B Drew; Ashutosh Ghosh
Journal: Inorg Chem Date: 2008-05-06 Impact factor: 5.165

4. Addition of small molecules by Zn(II) and Cu(II) dinuclear complexes obtained by an amino-phenolic ligand. Crystal structures of the dinuclear zinc complex assembling butanolate and azide anions.

Authors: P Dapporto; M Formica; V Fusi; L Giorgi; M Micheloni; P Paoli; R Pontellini; P Rossi
Journal: Inorg Chem Date: 2001-11-19 Impact factor: 5.165

5. Manganese(III) Schiff base complexes: chemistry relevant to the copolymerization of epoxides and carbon dioxide.

Authors: Donald J Darensbourg; Eric B Frantz
Journal: Inorg Chem Date: 2007-06-19 Impact factor: 5.165

6. Synthesis and characterization of luminescent zinc(II) and cadmium(II) complexes with N,S-chelating Schiff base ligands.

Authors: Tatsuya Kawamoto; Masato Nishiwaki; Yasutaka Tsunekawa; Koichi Nozaki; Takumi Konno
Journal: Inorg Chem Date: 2008-03-18 Impact factor: 5.165

7. Dichloridobis(2-{1-[2-(1H-indol-3-yl)ethyl-iminio]eth-yl}phenolate-κO)zinc(II)-2-{1-[2-(1H-indol-3-yl)ethyl-iminio]eth-yl}phenolate (1/2).

Authors: Hapipah M Ali; Mohamed Ibrahim Mohamed Mustafa; Mohd Razali Rizal; Seik Weng Ng
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-04-26

8. Azide-bridged one-dimensional Mn(III) polymers: effects of side group of Schiff base ligands on structure and magnetism.

Authors: Mei Yuan; Fei Zhao; Wen Zhang; Zhe-Ming Wang; Song Gao
Journal: Inorg Chem Date: 2007-11-22 Impact factor: 5.165

9. Coordination chemistry of a pi-extended, rigid and redox-active tetrathiafulvalene-fused Schiff-base ligand.

Authors: Jin-Cai Wu; Shi-Xia Liu; Tony D Keene; Antonia Neels; Valeriu Mereacre; Annie K Powell; Silvio Decurtins
Journal: Inorg Chem Date: 2008-04-21 Impact factor: 5.165

10. Binuclear fluoro-bridged zinc and cadmium complexes of a schiff base expanded porphyrin: fluoride abstraction from the tetrafluoroborate anion.

Authors: Elisa Tomat; Luciano Cuesta; Vincent M Lynch; Jonathan L Sessler
Journal: Inorg Chem Date: 2007-07-14 Impact factor: 5.165

6 in total