Literature DB >> 21201988

2-Amino-pyridinium (2-amino-pyridine)trichloridonickelate(II).

Hoong-Kun Fun, S Franklin, Samuel Robinson Jebas, T Balasubramanian.

Abstract

In the title compound, (C(5)H(7)N(2))[NiCl(3)(C(5)H(6)N(2))], the Ni(II) atom is four-coordinated by three chloride anions and one N atom of a 2-amino-pyridine ligand, forming a distorted tetra-hedral coordination. In the crystal structure, cations and complex anions are linked into chains along the a, b and c axes by N-H⋯Cl hydrogen bonds, leading to the formation of a three-dimensional framework.

Entities: Chemical Disease Species

Year: 2008 PMID： 21201988 PMCID： PMC2961041 DOI： 10.1107/S1600536808005655

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

Related literature

For related literature, see: Batsanov & Howard (2001 ▶); Bis & Zaworotko (2005 ▶); Chao et al. (1975 ▶); Corain et al. (1985 ▶); Jebas et al. (2006 ▶); Valdés-Martínez et al. (2001 ▶); Sletten & Kovacs (1993 ▶); Smith et al. (2000 ▶, 2001 ▶); Stibrany et al. (2004 ▶); Wei & Willett (1995 ▶); Windholz (1976 ▶).

Experimental

Crystal data

(C5H7N2)[NiCl3(C5H6N2)] M = 354.3 Monoclinic, a = 12.9265 (1) Å b = 8.0644 (1) Å c = 13.9893 (1) Å β = 106.163 (1)° V = 1400.67 (2) Å3 Z = 4 Mo Kα radiation μ = 1.94 mm−1 T = 100.0 (1) K 0.37 × 0.08 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer with Oxford Cryosystems Cobra low-temperature attachment Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.533, T max = 0.876 19539 measured reflections 6427 independent reflections 5088 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.079 S = 1.05 6427 reflections 167 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.52 e Å−3 Δρmin = −0.64 e Å−3 Absolute structure: Flack (1983 ▶), 1953 Friedel pairs Flack parameter: 0.065 (9) Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005655/ci2566sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005655/ci2566Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C₅H₇N₂)[NiCl₃(C₅H₆N₂)]	F₀₀₀ = 720
M_r = 354.3	D_x = 1.68 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 8411 reflections
a = 12.9265 (1) Å	θ = 3.0–30.6º
b = 8.0644 (1) Å	µ = 1.94 mm⁻¹
c = 13.9893 (1) Å	T = 100.0 (1) K
β = 106.163 (1)º	Block, blue
V = 1400.67 (2) Å³	0.37 × 0.08 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5088 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.031
ω scans	θ_max = 40.6º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	θ_min = 3.0º
T_min = 0.533, T_max = 0.876	h = −23→23
19539 measured reflections	k = −14→14
6427 independent reflections	l = −25→16

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.035	(Δ/σ)_max < 0.001
wR(F²) = 0.079	Δρ_max = 0.52 e Å⁻³
S = 1.05	Δρ_min = −0.64 e Å⁻³
6427 reflections	Extinction correction: none
167 parameters	Absolute structure: Flack (1983), 1953 Friedel pairs
2 restraints	Flack parameter: 0.065 (9)

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
Ni1	0.245028 (18)	0.65589 (3)	0.188212 (18)	0.01865 (6)
Cl1	0.40142 (4)	0.66552 (7)	0.14504 (4)	0.01889 (9)
Cl2	0.19741 (4)	0.38637 (6)	0.19116 (4)	0.02255 (10)
Cl3	0.10912 (4)	0.79387 (7)	0.07906 (4)	0.02299 (10)
N1	0.26459 (13)	0.7760 (2)	0.31947 (12)	0.0157 (3)
N2	0.30301 (15)	0.5422 (2)	0.41934 (14)	0.0228 (4)
H2B	0.2895	0.4816	0.3667	0.027*
H2C	0.322	0.4966	0.4772	0.027*
N3	0.55299 (14)	0.0900 (2)	0.44965 (14)	0.0191 (3)
N4	0.53731 (16)	−0.1509 (2)	0.35719 (15)	0.0228 (4)
H4B	0.5574	−0.2072	0.4114	0.027*
H4C	0.5224	−0.2007	0.3006	0.027*
C1	0.29457 (15)	0.7074 (3)	0.41122 (15)	0.0181 (4)
C2	0.31669 (17)	0.8074 (3)	0.49792 (16)	0.0213 (4)
H2A	0.3384	0.7591	0.5607	0.026*
C3	0.30568 (17)	0.9761 (3)	0.48792 (18)	0.0254 (4)
H3A	0.3199	1.0431	0.5442	0.03*
C4	0.27352 (17)	1.0463 (3)	0.39438 (18)	0.0245 (4)
H4A	0.2652	1.1605	0.3867	0.029*
C5	0.25411 (16)	0.9441 (3)	0.31322 (17)	0.0198 (4)
H5A	0.2326	0.992	0.2503	0.024*
C6	0.52944 (15)	0.0123 (2)	0.36071 (15)	0.0173 (3)
C7	0.49768 (16)	0.1116 (3)	0.27449 (16)	0.0203 (4)
H7A	0.4813	0.0628	0.2118	0.024*
C8	0.49108 (16)	0.2795 (3)	0.28322 (16)	0.0217 (4)
H8A	0.4704	0.3447	0.2262	0.026*
C9	0.51508 (17)	0.3550 (3)	0.37731 (18)	0.0229 (4)
H9A	0.5093	0.4693	0.3832	0.027*
C10	0.54691 (16)	0.2575 (3)	0.45963 (17)	0.0222 (4)
H10A	0.5645	0.3051	0.5227	0.027*
H1N3	0.571 (2)	0.030 (3)	0.499 (2)	0.023 (7)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02016 (11)	0.02167 (12)	0.01419 (12)	−0.00140 (10)	0.00489 (9)	−0.00168 (10)
Cl1	0.0188 (2)	0.0211 (2)	0.0179 (2)	−0.00022 (15)	0.00699 (18)	−0.00025 (16)
Cl2	0.0285 (2)	0.0194 (2)	0.0211 (2)	−0.00610 (19)	0.0092 (2)	−0.00511 (18)
Cl3	0.0208 (2)	0.0324 (3)	0.0142 (2)	0.00279 (19)	0.00214 (17)	0.00196 (19)
N1	0.0151 (7)	0.0181 (7)	0.0133 (7)	−0.0002 (6)	0.0030 (6)	0.0000 (6)
N2	0.0313 (9)	0.0201 (9)	0.0150 (8)	0.0021 (7)	0.0032 (7)	0.0003 (6)
N3	0.0170 (7)	0.0273 (9)	0.0132 (8)	0.0013 (6)	0.0043 (6)	0.0020 (7)
N4	0.0283 (9)	0.0220 (8)	0.0168 (9)	−0.0019 (7)	0.0038 (7)	0.0029 (6)
C1	0.0146 (8)	0.0238 (10)	0.0165 (9)	0.0012 (6)	0.0053 (7)	0.0011 (7)
C2	0.0180 (8)	0.0307 (11)	0.0149 (9)	−0.0009 (7)	0.0043 (7)	−0.0018 (8)
C3	0.0224 (9)	0.0269 (11)	0.0278 (12)	−0.0030 (8)	0.0087 (9)	−0.0105 (9)
C4	0.0251 (10)	0.0189 (9)	0.0309 (12)	−0.0026 (8)	0.0099 (9)	−0.0067 (9)
C5	0.0195 (8)	0.0179 (9)	0.0224 (10)	−0.0007 (7)	0.0065 (8)	−0.0002 (8)
C6	0.0153 (8)	0.0220 (9)	0.0142 (9)	−0.0021 (7)	0.0035 (7)	0.0011 (7)
C7	0.0183 (8)	0.0269 (10)	0.0145 (9)	0.0001 (7)	0.0023 (7)	0.0026 (8)
C8	0.0201 (9)	0.0261 (10)	0.0185 (10)	0.0034 (8)	0.0050 (8)	0.0059 (8)
C9	0.0204 (9)	0.0225 (10)	0.0272 (12)	0.0019 (7)	0.0092 (9)	−0.0010 (8)
C10	0.0183 (8)	0.0288 (11)	0.0200 (10)	0.0008 (8)	0.0062 (8)	−0.0052 (8)

Ni1—N1	2.0287 (17)	C2—C3	1.371 (3)
Ni1—Cl2	2.2625 (6)	C2—H2A	0.93
Ni1—Cl1	2.2665 (5)	C3—C4	1.380 (3)
Ni1—Cl3	2.2722 (6)	C3—H3A	0.93
N1—C1	1.352 (3)	C4—C5	1.369 (3)
N1—C5	1.363 (3)	C4—H4A	0.93
N2—C1	1.339 (3)	C5—H5A	0.93
N2—H2B	0.86	C6—C7	1.410 (3)
N2—H2C	0.86	C7—C8	1.364 (3)
N3—C6	1.350 (3)	C7—H7A	0.93
N3—C10	1.362 (3)	C8—C9	1.404 (3)
N3—H1N3	0.82 (3)	C8—H8A	0.93
N4—C6	1.322 (3)	C9—C10	1.360 (3)
N4—H4B	0.86	C9—H9A	0.93
N4—H4C	0.86	C10—H10A	0.93
C1—C2	1.417 (3)

N1—Ni1—Cl2	114.10 (5)	C2—C3—C4	120.0 (2)
N1—Ni1—Cl1	109.21 (5)	C2—C3—H3A	120
Cl2—Ni1—Cl1	107.77 (2)	C4—C3—H3A	120
N1—Ni1—Cl3	104.63 (5)	C5—C4—C3	118.5 (2)
Cl2—Ni1—Cl3	108.62 (2)	C5—C4—H4A	120.8
Cl1—Ni1—Cl3	112.60 (2)	C3—C4—H4A	120.8
C1—N1—C5	117.72 (18)	N1—C5—C4	123.6 (2)
C1—N1—Ni1	126.48 (14)	N1—C5—H5A	118.2
C5—N1—Ni1	115.59 (13)	C4—C5—H5A	118.2
C1—N2—H2B	120	N4—C6—N3	119.8 (2)
C1—N2—H2C	120	N4—C6—C7	122.7 (2)
H2B—N2—H2C	120	N3—C6—C7	117.51 (19)
C6—N3—C10	123.36 (19)	C8—C7—C6	119.8 (2)
C6—N3—H1N3	115.9 (18)	C8—C7—H7A	120.1
C10—N3—H1N3	120.7 (18)	C6—C7—H7A	120.1
C6—N4—H4B	120	C7—C8—C9	120.7 (2)
C6—N4—H4C	120	C7—C8—H8A	119.6
H4B—N4—H4C	120	C9—C8—H8A	119.6
N2—C1—N1	118.88 (18)	C10—C9—C8	118.6 (2)
N2—C1—C2	120.05 (19)	C10—C9—H9A	120.7
N1—C1—C2	121.1 (2)	C8—C9—H9A	120.7
C3—C2—C1	119.1 (2)	C9—C10—N3	119.9 (2)
C3—C2—H2A	120.4	C9—C10—H10A	120
C1—C2—H2A	120.4	N3—C10—H10A	120

Cl2—Ni1—N1—C1	28.37 (17)	C2—C3—C4—C5	−0.5 (3)
Cl1—Ni1—N1—C1	−92.28 (15)	C1—N1—C5—C4	0.8 (3)
Cl3—Ni1—N1—C1	146.95 (15)	Ni1—N1—C5—C4	−174.29 (16)
Cl2—Ni1—N1—C5	−156.98 (11)	C3—C4—C5—N1	0.1 (3)
Cl1—Ni1—N1—C5	82.36 (13)	C10—N3—C6—N4	179.99 (18)
Cl3—Ni1—N1—C5	−38.41 (13)	C10—N3—C6—C7	0.4 (3)
C5—N1—C1—N2	178.47 (16)	N4—C6—C7—C8	179.96 (19)
Ni1—N1—C1—N2	−7.0 (3)	N3—C6—C7—C8	−0.5 (3)
C5—N1—C1—C2	−1.4 (3)	C6—C7—C8—C9	−0.3 (3)
Ni1—N1—C1—C2	173.14 (13)	C7—C8—C9—C10	1.1 (3)
N2—C1—C2—C3	−178.84 (18)	C8—C9—C10—N3	−1.2 (3)
N1—C1—C2—C3	1.0 (3)	C6—N3—C10—C9	0.5 (3)
C1—C2—C3—C4	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···Cl2ⁱ	0.82 (3)	2.81 (3)	3.380 (2)	128 (2)
N2—H2B···Cl2	0.86	2.53	3.3475 (19)	159
N2—H2C···Cl1ⁱⁱ	0.86	2.63	3.4866 (19)	172
N4—H4B···Cl3ⁱ	0.86	2.36	3.197 (2)	165
N4—H4C···Cl1ⁱⁱⁱ	0.86	2.54	3.344 (2)	156

Ni1—N1	2.0287 (17)
Ni1—Cl2	2.2625 (6)
Ni1—Cl1	2.2665 (5)
Ni1—Cl3	2.2722 (6)

N1—Ni1—Cl2	114.10 (5)
N1—Ni1—Cl1	109.21 (5)
Cl2—Ni1—Cl1	107.77 (2)
N1—Ni1—Cl3	104.63 (5)
Cl2—Ni1—Cl3	108.62 (2)
Cl1—Ni1—Cl3	112.60 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯Cl2ⁱ	0.82 (3)	2.81 (3)	3.380 (2)	128 (2)
N2—H2B⋯Cl2	0.86	2.53	3.3475 (19)	159
N2—H2C⋯Cl1ⁱⁱ	0.86	2.63	3.4866 (19)	172
N4—H4B⋯Cl3ⁱ	0.86	2.36	3.197 (2)	165
N4—H4C⋯Cl1ⁱⁱⁱ	0.86	2.54	3.344 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) .

2 in total

1. The 1:1 adduct of Kemp's triacid with 2-aminopyridine

Authors:
Journal: Acta Crystallogr C Date: 2000-12 Impact factor: 1.172

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

2 in total