Literature DB >> 21201317

[Bis(2-pyridylmeth-yl)amine]dichloridomercury(II).

Young-Inn Kim, You-Soon Lee, Hoe-Joo Seo, Ki-Sun Nam, Sung Kwon Kang.

Abstract

The Hg atom in the title complex, [HgCl(2)(C(12)H(13)N(3))], adopts a square-pyramidal geometry, being ligated by three N atoms of the tridentate bis-(2-pyridylmeth-yl)amine ligand and two Cl atoms, with one of the latter occupying the apical position. Disorder is noted in the amine portion of the ligand and this was modelled over two sites, with the major component having a site-occupancy factor of 0.794 (14).

Entities: Chemical Disease Species

Year: 2008 PMID： 21201317 PMCID： PMC2960290 DOI： 10.1107/S1600536808000858

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

Related literature

For general background, see: Ojida et al. (2004 ▶); Kirin et al. (2005 ▶); Storr et al. (2005 ▶); Tamamura et al. (2006 ▶); Kim et al. (2007 ▶); Lee et al. (2007 ▶). For related literature, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[HgCl2(C12H13N3)] M = 470.74 Monoclinic, a = 8.4083 (6) Å b = 12.8278 (11) Å c = 13.3457 (12) Å β = 90.462 (2)° V = 1439.4 (2) Å3 Z = 4 Mo Kα radiation μ = 11.05 mm−1 T = 295 (2) K 0.18 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.143, T max = 0.185 15603 measured reflections 3580 independent reflections 2547 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.061 S = 1.01 3580 reflections 173 parameters H-atom parameters constrained Δρmax = 1.22 e Å−3 Δρmin = −0.47 e Å−3 Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000858/tk2241sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000858/tk2241Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[HgCl₂(C₁₂H₁₃N₃)]	F₀₀₀ = 880
M_r = 470.74	D_x = 2.172 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4387 reflections
a = 8.4083 (6) Å	θ = 2.2–24.5º
b = 12.8278 (11) Å	µ = 11.05 mm⁻¹
c = 13.3457 (12) Å	T = 295 (2) K
β = 90.462 (2)º	Block, orange
V = 1439.4 (2) Å³	0.18 × 0.15 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	R_int = 0.028
φ and ω scans	θ_max = 28.3º
Absorption correction: multi-scan(SADABS; Bruker, 2002)	θ_min = 2.2º
T_min = 0.143, T_max = 0.185	h = −11→11
15603 measured reflections	k = −12→17
3580 independent reflections	l = −17→17
2547 reflections with I > 2σ(I)

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0268P)² + 0.7364P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.027	(Δ/σ)_max = 0.002
wR(F²) = 0.061	Δρ_max = 1.22 e Å⁻³
S = 1.02	Δρ_min = −0.47 e Å⁻³
3580 reflections	Extinction correction: none
173 parameters

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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
Hg	0.87912 (2)	0.305769 (14)	0.873548 (12)	0.06174 (8)
Cl1	1.04268 (15)	0.36276 (12)	0.73426 (9)	0.0791 (3)
Cl2	0.63148 (16)	0.21091 (10)	0.83674 (11)	0.0794 (4)
N1	1.0536 (5)	0.1777 (3)	0.9449 (3)	0.0636 (10)
C2	1.1638 (6)	0.1270 (4)	0.8923 (4)	0.0799 (14)
H2	1.1708	0.1399	0.8239	0.096*
C3	1.2665 (7)	0.0573 (5)	0.9348 (5)	0.0911 (17)
H3	1.3425	0.0235	0.8963	0.109*
C4	1.2548 (7)	0.0381 (5)	1.0354 (6)	0.0959 (18)
H4	1.3227	−0.0093	1.0665	0.115*
C5	1.1423 (6)	0.0898 (4)	1.0893 (4)	0.0792 (14)
H5	1.1332	0.0779	1.1578	0.095*
C6	1.0426 (5)	0.1592 (3)	1.0422 (3)	0.0576 (10)
C7	0.9172 (6)	0.2192 (4)	1.0981 (4)	0.0727 (13)
H7A	0.815	0.1847	1.0914	0.087*
H7B	0.9447	0.2228	1.1688	0.087*
N8	0.9085 (9)	0.3260 (5)	1.0549 (3)	0.0594 (19)	0.794 (14)
H8	1.0033	0.358	1.0671	0.071*	0.794 (14)
N8A	0.807 (3)	0.2914 (15)	1.0593 (11)	0.048 (7)	0.206 (14)
H8A	0.7101	0.2599	1.0615	0.057*	0.206 (14)
C9	0.7863 (6)	0.3898 (4)	1.0952 (3)	0.0746 (14)
H9A	0.8204	0.4161	1.1601	0.09*
H9B	0.6918	0.3478	1.1053	0.09*
C10	0.7454 (5)	0.4802 (4)	1.0282 (3)	0.0590 (11)
C11	0.6733 (5)	0.5697 (4)	1.0649 (4)	0.0707 (13)
H11	0.6523	0.5763	1.1329	0.085*
C12	0.6337 (6)	0.6482 (4)	0.9995 (4)	0.0766 (14)
H12	0.5842	0.7081	1.0229	0.092*
C13	0.6666 (6)	0.6383 (4)	0.9010 (4)	0.0742 (13)
H13	0.6408	0.6912	0.856	0.089*
C14	0.7391 (5)	0.5482 (4)	0.8685 (3)	0.0669 (12)
H14	0.7622	0.5413	0.8007	0.08*
N15	0.7774 (4)	0.4704 (3)	0.9307 (2)	0.0563 (8)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg	0.07430 (13)	0.06556 (13)	0.04548 (10)	0.01047 (9)	0.00744 (7)	0.00080 (8)
Cl1	0.0815 (8)	0.0984 (10)	0.0575 (6)	−0.0078 (7)	0.0157 (6)	0.0109 (6)
Cl2	0.0726 (8)	0.0803 (9)	0.0857 (9)	−0.0067 (6)	0.0138 (6)	−0.0032 (6)
N1	0.061 (2)	0.064 (2)	0.066 (2)	0.0019 (18)	0.0042 (18)	0.0070 (18)
C2	0.078 (3)	0.077 (4)	0.085 (3)	0.010 (3)	0.020 (3)	−0.004 (3)
C3	0.074 (4)	0.069 (4)	0.130 (5)	0.010 (3)	0.010 (3)	−0.020 (4)
C4	0.075 (4)	0.072 (4)	0.140 (6)	0.014 (3)	−0.019 (4)	0.006 (4)
C5	0.077 (3)	0.076 (3)	0.084 (3)	0.000 (3)	−0.009 (3)	0.017 (3)
C6	0.056 (3)	0.053 (2)	0.064 (3)	−0.007 (2)	−0.004 (2)	0.008 (2)
C7	0.073 (3)	0.086 (4)	0.059 (3)	0.001 (3)	0.000 (2)	0.017 (3)
N8	0.051 (4)	0.067 (4)	0.060 (3)	−0.003 (3)	0.004 (2)	0.003 (2)
N8A	0.046 (14)	0.053 (12)	0.045 (9)	−0.007 (9)	−0.002 (7)	0.009 (7)
C9	0.089 (4)	0.082 (4)	0.053 (3)	0.000 (3)	0.011 (2)	−0.003 (2)
C10	0.058 (3)	0.063 (3)	0.056 (2)	−0.009 (2)	0.0045 (19)	−0.012 (2)
C11	0.068 (3)	0.076 (3)	0.068 (3)	−0.005 (3)	0.010 (2)	−0.022 (3)
C12	0.058 (3)	0.062 (3)	0.109 (4)	0.002 (2)	−0.001 (3)	−0.021 (3)
C13	0.068 (3)	0.064 (3)	0.090 (4)	−0.003 (3)	−0.003 (3)	0.003 (3)
C14	0.074 (3)	0.061 (3)	0.066 (3)	−0.006 (2)	0.006 (2)	−0.001 (2)
N15	0.060 (2)	0.058 (2)	0.0507 (19)	−0.0047 (17)	0.0061 (16)	−0.0016 (16)

Hg—Cl1	2.4336 (12)	C7—H7A	0.97
Hg—Cl2	2.4579 (14)	C7—H7B	0.97
Hg—N1	2.394 (4)	N8—C9	1.423 (7)
Hg—N8	2.445 (5)	N8—H8	0.91
Hg—N15	2.405 (4)	N8A—C9	1.362 (18)
Hg—N8A	2.563 (17)	N8A—H8A	0.91
N1—C6	1.325 (6)	C9—C10	1.503 (7)
N1—C2	1.336 (6)	C9—H9A	0.97
C2—C3	1.364 (7)	C9—H9B	0.97
C2—H2	0.93	C10—N15	1.336 (5)
C3—C4	1.370 (8)	C10—C11	1.389 (6)
C3—H3	0.93	C11—C12	1.372 (7)
C4—C5	1.365 (8)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.351 (7)
C5—C6	1.372 (6)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.379 (7)
C6—C7	1.508 (7)	C13—H13	0.93
C7—N8A	1.407 (18)	C14—N15	1.337 (6)
C7—N8	1.488 (7)	C14—H14	0.93

Cl1—Hg—Cl2	118.63 (5)	H7A—C7—H7B	108.4
N1—Hg—N8	67.82 (15)	C9—N8—C7	114.6 (5)
N1—Hg—N15	133.99 (12)	C9—N8—Hg	111.6 (3)
N8—Hg—N15	68.04 (14)	C7—N8—Hg	106.9 (3)
N1—Hg—Cl1	99.30 (10)	C9—N8—H8	107.8
N15—Hg—Cl1	100.55 (9)	C7—N8—H8	107.8
Cl1—Hg—N8	132.16 (19)	Hg—N8—H8	107.8
N1—Hg—Cl2	104.77 (10)	C9—N8A—C7	124.5 (15)
N15—Hg—Cl2	101.26 (9)	C9—N8A—Hg	107.8 (10)
N8—Hg—Cl2	109.21 (19)	C7—N8A—Hg	104.1 (10)
N1—Hg—N8A	73.5 (4)	C9—N8A—H8A	106.4
N15—Hg—N8A	70.7 (4)	C7—N8A—H8A	106.4
Cl1—Hg—N8A	154.1 (6)	Hg—N8A—H8A	106.4
N8—Hg—N8A	22.0 (5)	N8A—C9—C10	122.3 (7)
Cl2—Hg—N8A	87.2 (6)	N8—C9—C10	112.4 (4)
C6—N1—C2	118.8 (4)	N8A—C9—H9A	126.8
C6—N1—Hg	117.8 (3)	N8—C9—H9A	109.1
C2—N1—Hg	123.4 (3)	C10—C9—H9A	109.1
N1—C2—C3	122.7 (5)	N8—C9—H9B	109.1
N1—C2—H2	118.6	C10—C9—H9B	109.1
C3—C2—H2	118.6	H9A—C9—H9B	107.9
C2—C3—C4	118.4 (5)	N15—C10—C11	120.9 (5)
C2—C3—H3	120.8	N15—C10—C9	117.4 (4)
C4—C3—H3	120.8	C11—C10—C9	121.7 (4)
C5—C4—C3	119.1 (5)	C12—C11—C10	119.1 (5)
C5—C4—H4	120.5	C12—C11—H11	120.5
C3—C4—H4	120.5	C10—C11—H11	120.5
C4—C5—C6	119.8 (5)	C13—C12—C11	120.0 (5)
C4—C5—H5	120.1	C13—C12—H12	120
C6—C5—H5	120.1	C11—C12—H12	120
N1—C6—C5	121.3 (5)	C12—C13—C14	118.6 (5)
N1—C6—C7	116.6 (4)	C12—C13—H13	120.7
C5—C6—C7	122.1 (4)	C14—C13—H13	120.7
N8A—C7—C6	127.9 (8)	N15—C14—C13	122.4 (4)
N8—C7—C6	108.1 (4)	N15—C14—H14	118.8
N8—C7—H7A	110.1	C13—C14—H14	118.8
C6—C7—H7A	110.1	C10—N15—C14	119.0 (4)
N8A—C7—H7B	118.6	C10—N15—Hg	117.8 (3)
N8—C7—H7B	110.1	C14—N15—Hg	122.9 (3)
C6—C7—H7B	110.1

Hg—Cl1	2.4336 (12)
Hg—Cl2	2.4579 (14)
Hg—N1	2.394 (4)
Hg—N8	2.445 (5)
Hg—N15	2.405 (4)

Cl1—Hg—Cl2	118.63 (5)
N1—Hg—N8	67.82 (15)
N1—Hg—N15	133.99 (12)
N8—Hg—N15	68.04 (14)

5 in total

1. Identification of a new class of low molecular weight antagonists against the chemokine receptor CXCR4 having the dipicolylamine-zinc(II) complex structure.

Authors: Hirokazu Tamamura; Akio Ojida; Teppei Ogawa; Hiroshi Tsutsumi; Hiroyuki Masuno; Hideki Nakashima; Naoki Yamamoto; Itaru Hamachi; Nobutaka Fujii
Journal: J Med Chem Date: 2006-06-01 Impact factor: 7.446

2. A short history of SHELX.

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

3. Carbohydrate-appended 2,2'-dipicolylamine metal complexes as potential imaging agents.

Authors: Tim Storr; Yuko Sugai; Cheri A Barta; Yuji Mikata; Michael J Adam; Shigenobu Yano; Chris Orvig
Journal: Inorg Chem Date: 2005-04-18 Impact factor: 5.165

4. Amino acid and peptide bioconjugates of copper(II) and zinc(II) complexes with a modified N,N-bis(2-picolyl)amine ligand.

Authors: Srećko I Kirin; Pierre Dübon; Thomas Weyhermüller; Eckhard Bill; Nils Metzler-Nolte
Journal: Inorg Chem Date: 2005-07-25 Impact factor: 5.165

5. Molecular recognition and fluorescence sensing of monophosphorylated peptides in aqueous solution by bis(zinc(II)-dipicolylamine)-based artificial receptors.

Authors: Akio Ojida; Yasuko Mito-oka; Kazuki Sada; Itaru Hamachi
Journal: J Am Chem Soc Date: 2004-03-03 Impact factor: 15.419