Tetra­kis[3-(2-pyridylamino)pyridine-κN]nickel(II) diperchlorate ethanol disolvate

Wang, Z.-M.

doi:10.1107/S1600536808006569

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m540

doi:10.1107/S1600536808006569

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Tetrakis[3-(2-pyridylamino)pyridine-κN]nickel(II) diperchlorate ethanol disolvate

Zhi-Min Wang ^a ^*

^aCollege of Biology and Environment Engineering, Zhejiang Shuren University, Hangzhou 310015, People's Republic of China
^*Correspondence e-mail: hslj2004@126.com

(Received 7 March 2008; accepted 9 March 2008; online 14 March 2008)

In the title compound, [Ni(C₁₀H₉N₃)₄](ClO₄)₂·2C₂H₅OH, the metal centre exhibits a four-coordinated environment with four pyridine N atoms of the four different dipyridylamine ligands. A twofold rotation axis passes through the Ni atom. N—H⋯O and N—H⋯N hydrogen bonds are present in the crystal structure.

Related literature

For related literature, see: Moulton & Zaworotko (2001 ); Su et al. (2003 ); Zhou et al. (2006 ); Biradha et al. (1999 ); Gudbjartson et al. (1999 ).

Experimental

Crystal data

[Ni(C₁₀H₉N₃)₄](ClO₄)₂·2C₂H₆O
M_r = 1034.55
Monoclinic, C 2/c
a = 27.767 (4) Å
b = 10.7067 (14) Å
c = 18.144 (2) Å
β = 115.891 (9)°
V = 4852.6 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 298 (2) K
0.32 × 0.22 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.836, T_max = 0.908
11042 measured reflections
4315 independent reflections
2875 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.134
S = 1.08
4315 reflections
314 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5B⋯O5	0.86	2.07	2.928 (5)	174
N2—H2⋯N6ⁱ	0.86	2.27	3.129 (4)	176
Symmetry code: (i) x, y-1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006569/at2548sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006569/at2548Isup2.hkl

checkCIF report

Comment top

In recent years, the rational design and assembly of metal-organic frameworks (MOFs) with well regulated network structures have received remarkable attention in order to develop new functional materials with potential applications (Moulton & Zaworotko, 2001). Nevertheless, it is still a great challenge to predict the exact structures and compositions of polymeric compounds assembled in a helical motif, although some structures with various helices have been reported in MOFs. So far, much of the research has been concentrated on the exploitation of angular ligands with a molecular angle, such as ligands with a T-shape, V-shape etc, in the construction of versatile coordination polymer architectures (Gudbjartson et al., 1999; Su et al., 2003, Zhou et al., 2006). In this paper, we report the synthesis and crystal structure of the title complex with a V-shaped ligand,(I).

As shown in Fig. 1, the complex I is located twofold axis via the 2,3'-dipyridylamine (L) ligands. That I is a neutral, mononuclear molecule with the Ni(II) atom in a square coordination geometry with four pyridine nitrogen atoms of the four different L ligands. The Ni—N bond lengths range from 2.013 (2) to 2.019 (2)Å (Table1), and the N(1)—Ni—N(4) angle is 179.09 (11)°, it can be seen that the Ni(II) ions together with the four nitrogen atoms form a perfect square geometry, and this ideal quadrangle structure is rare in the coordination geometry of Ni(II) atom. Four L ligands present monodenate fashion. Two O atoms of the uncoordinated ClO₄ anions form the acceptors of intermolecular hydrogen bonds and weak interactions, which link the discrete units to form a two-dimensional supramolecular structure. The ethanol molecule present in I only functioned as an acceptor of intramolecular hydrogen bonds between the oxygen atoms of ethonal and amino nitrogen atoms of the ligand (Table 2), which stabilize the extended structure.

Related literature top

For related literature, see: Moulton & Zaworotko (2001); Su et al. (2003); Zhou et al. (2006); Biradha et al. (1999); Gudbjartson et al. (1999).

Experimental top

NiClO₄(0.027 g, 0.013 mmol), L (0.025 g, 0.014 mmol) were added in a solvent of methanol, the mixture was heated for 6 h under reflux. During the process stirring and influx were required. The resultant was then filtered to give a pure solution which was infiltrated by diethyl ether freely in a closed vessel, Two weeks later some single crystals of the size suitable for X-Ray diffraction analysis.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of (I), showing 30% probability displacement ellipsoids [symmetrical code: (i) -x, y, 1/2 - z].

Tetrakis[3-(2-pyridylamino)pyridine-κN]nickel(II) bis(perchlorate) ethanol disolvate top

Crystal data top

[Ni(C₁₀H₉N₃)₄](ClO₄)₂·2C₂H₆O	F(000) = 2152
M_r = 1034.55	D_x = 1.416 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4315 reflections
a = 27.767 (4) Å	θ = 1.6–25.1°
b = 10.7067 (14) Å	µ = 0.58 mm⁻¹
c = 18.144 (2) Å	T = 298 K
β = 115.891 (9)°	Block, green
V = 4852.6 (11) Å³	0.32 × 0.22 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4315 independent reflections
Radiation source: fine-focus sealed tube	2875 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −33→33
T_min = 0.836, T_max = 0.908	k = −12→12
11042 measured reflections	l = −21→21

Refinement top

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0501P)² + 1.1196P] where P = (F_o² + 2F_c²)/3
4315 reflections	(Δ/σ)_max = 0.084
314 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Ni(C₁₀H₉N₃)₄](ClO₄)₂·2C₂H₆O	V = 4852.6 (11) Å³
M_r = 1034.55	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 27.767 (4) Å	µ = 0.58 mm⁻¹
b = 10.7067 (14) Å	T = 298 K
c = 18.144 (2) Å	0.32 × 0.22 × 0.17 mm
β = 115.891 (9)°

Data collection top

Bruker APEXII area-detector diffractometer	4315 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2875 reflections with I > 2σ(I)
T_min = 0.836, T_max = 0.908	R_int = 0.044
11042 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.08	Δρ_max = 0.35 e Å⁻³
4315 reflections	Δρ_min = −0.36 e Å⁻³
314 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.23720 (5)	0.7500	0.0397 (2)
N1	0.54118 (10)	0.1032 (2)	0.72421 (16)	0.0455 (6)
N2	0.60983 (11)	−0.1938 (3)	0.80972 (17)	0.0586 (8)
H2	0.6337	−0.2349	0.8016	0.070*
N3	0.56191 (11)	−0.1786 (3)	0.88745 (18)	0.0577 (7)
N4	0.54239 (10)	0.3700 (2)	0.72509 (16)	0.0438 (6)
N5	0.68140 (10)	0.4606 (3)	0.79766 (17)	0.0550 (7)
H5B	0.6945	0.3923	0.8237	0.066*
N6	0.69860 (11)	0.6684 (3)	0.77848 (18)	0.0574 (7)
C1	0.56303 (12)	0.0085 (3)	0.77601 (19)	0.0456 (8)
H1	0.5621	0.0104	0.8267	0.055*
C2	0.58706 (13)	−0.0930 (3)	0.7574 (2)	0.0474 (8)
C3	0.58891 (14)	−0.0912 (3)	0.6822 (2)	0.0547 (9)
H3	0.6051	−0.1566	0.6677	0.066*
C4	0.56711 (14)	0.0061 (3)	0.6297 (2)	0.0565 (9)
H4	0.5684	0.0073	0.5794	0.068*
C5	0.54302 (13)	0.1029 (3)	0.6514 (2)	0.0515 (8)
H5	0.5279	0.1687	0.6152	0.062*
C6	0.59913 (15)	−0.2364 (3)	0.8729 (2)	0.0544 (9)
C7	0.62701 (16)	−0.3403 (4)	0.9173 (2)	0.0682 (11)
H7	0.6529	−0.3791	0.9058	0.082*
C8	0.61504 (17)	−0.3838 (4)	0.9787 (2)	0.0757 (11)
H8	0.6324	−0.4540	1.0089	0.091*
C9	0.57742 (17)	−0.3231 (4)	0.9951 (2)	0.0720 (11)
H9	0.5692	−0.3502	1.0369	0.086*
C10	0.55247 (15)	−0.2224 (4)	0.9489 (2)	0.0643 (10)
H10	0.5272	−0.1812	0.9606	0.077*
C11	0.59564 (12)	0.3773 (3)	0.76688 (19)	0.0437 (7)
H11	0.6127	0.3229	0.8106	0.052*
C12	0.62665 (12)	0.4614 (3)	0.74861 (19)	0.0426 (7)
C13	0.60115 (12)	0.5367 (3)	0.6812 (2)	0.0477 (8)
H13	0.6208	0.5904	0.6645	0.057*
C14	0.54629 (13)	0.5316 (3)	0.6387 (2)	0.0525 (8)
H14	0.5285	0.5841	0.5942	0.063*
C15	0.51777 (13)	0.4489 (3)	0.6622 (2)	0.0515 (8)
H15	0.4806	0.4475	0.6339	0.062*
C16	0.71742 (12)	0.5563 (3)	0.8097 (2)	0.0480 (8)
C17	0.77153 (13)	0.5330 (4)	0.8563 (2)	0.0653 (10)
H17	0.7835	0.4542	0.8784	0.078*
C18	0.80698 (16)	0.6289 (5)	0.8690 (3)	0.0827 (13)
H18	0.8434	0.6163	0.9007	0.099*
C19	0.78839 (18)	0.7437 (4)	0.8349 (3)	0.0815 (13)
H19	0.8118	0.8094	0.8415	0.098*
C20	0.73503 (16)	0.7584 (4)	0.7913 (3)	0.0701 (11)
H20	0.7226	0.8366	0.7686	0.084*
Cl1	0.39899 (4)	0.22782 (8)	0.51603 (5)	0.0580 (3)
O1	0.42456 (13)	0.2385 (3)	0.60132 (16)	0.0903 (10)
O2	0.43498 (15)	0.2706 (3)	0.4854 (2)	0.1180 (13)
O3	0.38628 (16)	0.1017 (3)	0.4956 (2)	0.1268 (14)
O4	0.35263 (17)	0.2973 (5)	0.4863 (4)	0.196 (2)
O5	0.7269 (3)	0.2376 (3)	0.8974 (3)	0.166 (2)
H5A	0.7075	0.2571	0.9190	0.249*
C21	0.7270 (3)	0.0252 (6)	0.9344 (4)	0.143 (2)
H21A	0.7532	0.0553	0.9863	0.215*
H21B	0.7396	−0.0506	0.9206	0.215*
H21C	0.6940	0.0094	0.9378	0.215*
C22	0.7186 (3)	0.1150 (6)	0.8741 (4)	0.151 (3)
H22A	0.7416	0.0948	0.8482	0.181*
H22B	0.6819	0.1068	0.8327	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0470 (3)	0.0271 (3)	0.0562 (4)	0.000	0.0329 (3)	0.000
N1	0.0539 (16)	0.0367 (15)	0.0564 (16)	0.0018 (12)	0.0340 (14)	0.0022 (13)
N2	0.070 (2)	0.0493 (17)	0.0644 (19)	0.0226 (15)	0.0365 (17)	0.0081 (15)
N3	0.0660 (19)	0.0489 (18)	0.0645 (19)	0.0046 (14)	0.0344 (17)	0.0068 (15)
N4	0.0470 (16)	0.0328 (14)	0.0556 (16)	0.0043 (12)	0.0261 (14)	0.0038 (13)
N5	0.0428 (16)	0.0420 (16)	0.071 (2)	0.0045 (12)	0.0166 (15)	0.0154 (14)
N6	0.0506 (17)	0.0438 (18)	0.073 (2)	−0.0016 (14)	0.0221 (16)	0.0044 (15)
C1	0.057 (2)	0.0342 (17)	0.0531 (19)	0.0017 (15)	0.0311 (17)	0.0019 (16)
C2	0.0508 (19)	0.0390 (18)	0.058 (2)	0.0035 (15)	0.0285 (17)	−0.0007 (16)
C3	0.065 (2)	0.046 (2)	0.064 (2)	0.0063 (17)	0.0384 (19)	−0.0056 (18)
C4	0.072 (2)	0.052 (2)	0.059 (2)	0.0061 (18)	0.041 (2)	0.0009 (18)
C5	0.063 (2)	0.046 (2)	0.058 (2)	0.0033 (16)	0.0376 (18)	0.0063 (17)
C6	0.061 (2)	0.044 (2)	0.054 (2)	0.0017 (17)	0.0212 (18)	−0.0013 (17)
C7	0.079 (3)	0.054 (2)	0.068 (3)	0.017 (2)	0.029 (2)	0.011 (2)
C8	0.086 (3)	0.056 (3)	0.065 (3)	0.003 (2)	0.014 (2)	0.012 (2)
C9	0.075 (3)	0.075 (3)	0.059 (2)	−0.012 (2)	0.023 (2)	0.014 (2)
C10	0.061 (2)	0.069 (3)	0.065 (2)	−0.0037 (19)	0.029 (2)	0.006 (2)
C11	0.045 (2)	0.0372 (18)	0.0494 (19)	0.0069 (14)	0.0213 (16)	0.0081 (15)
C12	0.0455 (18)	0.0325 (16)	0.0498 (18)	0.0019 (13)	0.0208 (16)	0.0001 (14)
C13	0.051 (2)	0.0383 (18)	0.054 (2)	−0.0073 (15)	0.0230 (17)	0.0052 (16)
C14	0.048 (2)	0.0414 (19)	0.057 (2)	−0.0002 (15)	0.0123 (17)	0.0124 (16)
C15	0.0446 (19)	0.0412 (19)	0.063 (2)	−0.0004 (15)	0.0184 (17)	0.0032 (17)
C16	0.0405 (18)	0.047 (2)	0.056 (2)	−0.0021 (15)	0.0204 (16)	−0.0038 (16)
C17	0.043 (2)	0.061 (2)	0.079 (3)	0.0068 (17)	0.0141 (19)	0.003 (2)
C18	0.043 (2)	0.095 (4)	0.101 (3)	−0.008 (2)	0.024 (2)	−0.006 (3)
C19	0.064 (3)	0.077 (3)	0.096 (3)	−0.026 (2)	0.029 (3)	−0.005 (3)
C20	0.067 (3)	0.054 (2)	0.078 (3)	−0.0135 (19)	0.022 (2)	0.006 (2)
Cl1	0.0655 (6)	0.0541 (6)	0.0529 (5)	−0.0062 (4)	0.0243 (5)	−0.0040 (4)
O1	0.104 (2)	0.120 (3)	0.0521 (16)	−0.0282 (18)	0.0392 (17)	−0.0173 (15)
O2	0.150 (3)	0.146 (3)	0.084 (2)	−0.053 (2)	0.076 (2)	0.000 (2)
O3	0.183 (4)	0.082 (2)	0.152 (3)	−0.060 (2)	0.106 (3)	−0.062 (2)
O4	0.095 (3)	0.162 (4)	0.274 (6)	0.057 (3)	0.026 (4)	0.053 (4)
O5	0.221 (6)	0.067 (2)	0.128 (4)	0.010 (3)	0.001 (3)	0.019 (2)
C21	0.189 (7)	0.092 (4)	0.147 (6)	−0.001 (4)	0.072 (5)	0.004 (4)
C22	0.187 (7)	0.080 (4)	0.129 (5)	−0.028 (4)	0.017 (5)	0.013 (4)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	2.013 (2)	C9—C10	1.356 (5)
Ni1—N1	2.013 (2)	C9—H9	0.9300
Ni1—N4	2.019 (2)	C10—H10	0.9300
Ni1—N4ⁱ	2.019 (2)	C11—C12	1.382 (4)
N1—C1	1.335 (4)	C11—H11	0.9300
N1—C5	1.344 (4)	C12—C13	1.375 (4)
N2—C6	1.382 (4)	C13—C14	1.375 (4)
N2—C2	1.393 (4)	C13—H13	0.9300
N2—H2	0.8600	C14—C15	1.373 (4)
N3—C6	1.326 (4)	C14—H14	0.9300
N3—C10	1.336 (4)	C15—H15	0.9300
N4—C11	1.337 (4)	C16—C17	1.388 (5)
N4—C15	1.342 (4)	C17—C18	1.371 (5)
N5—C16	1.381 (4)	C17—H17	0.9300
N5—C12	1.386 (4)	C18—C19	1.371 (6)
N5—H5B	0.8600	C18—H18	0.9300
N6—C16	1.332 (4)	C19—C20	1.350 (6)
N6—C20	1.342 (4)	C19—H19	0.9300
C1—C2	1.392 (4)	C20—H20	0.9300
C1—H1	0.9300	Cl1—O4	1.377 (4)
C2—C3	1.388 (4)	Cl1—O1	1.397 (3)
C3—C4	1.362 (5)	Cl1—O3	1.404 (3)
C3—H3	0.9300	Cl1—O2	1.415 (3)
C4—C5	1.381 (4)	O5—C22	1.368 (6)
C4—H4	0.9300	O5—H5A	0.8200
C5—H5	0.9300	C21—C22	1.397 (7)
C6—C7	1.394 (5)	C21—H21A	0.9600
C7—C8	1.376 (5)	C21—H21B	0.9600
C7—H7	0.9300	C21—H21C	0.9600
C8—C9	1.369 (5)	C22—H22A	0.9700
C8—H8	0.9300	C22—H22B	0.9700

N1ⁱ—Ni1—N1	89.08 (14)	N4—C11—C12	123.5 (3)
N1ⁱ—Ni1—N4	179.09 (11)	N4—C11—H11	118.2
N1—Ni1—N4	90.24 (10)	C12—C11—H11	118.2
N1ⁱ—Ni1—N4ⁱ	90.24 (10)	C13—C12—C11	117.5 (3)
N1—Ni1—N4ⁱ	179.09 (11)	C13—C12—N5	124.7 (3)
N4—Ni1—N4ⁱ	90.44 (13)	C11—C12—N5	117.7 (3)
C1—N1—C5	119.3 (3)	C12—C13—C14	119.3 (3)
C1—N1—Ni1	120.49 (19)	C12—C13—H13	120.4
C5—N1—Ni1	120.0 (2)	C14—C13—H13	120.4
C6—N2—C2	128.5 (3)	C15—C14—C13	120.0 (3)
C6—N2—H2	115.7	C15—C14—H14	120.0
C2—N2—H2	115.7	C13—C14—H14	120.0
C6—N3—C10	117.1 (3)	N4—C15—C14	121.4 (3)
C11—N4—C15	118.2 (3)	N4—C15—H15	119.3
C11—N4—Ni1	121.5 (2)	C14—C15—H15	119.3
C15—N4—Ni1	120.2 (2)	N6—C16—N5	118.6 (3)
C16—N5—C12	127.8 (3)	N6—C16—C17	122.7 (3)
C16—N5—H5B	116.1	N5—C16—C17	118.7 (3)
C12—N5—H5B	116.1	C18—C17—C16	118.4 (4)
C16—N6—C20	116.6 (3)	C18—C17—H17	120.8
N1—C1—C2	122.8 (3)	C16—C17—H17	120.8
N1—C1—H1	118.6	C17—C18—C19	119.6 (4)
C2—C1—H1	118.6	C17—C18—H18	120.2
C3—C2—C1	117.0 (3)	C19—C18—H18	120.2
C3—C2—N2	118.7 (3)	C20—C19—C18	118.0 (4)
C1—C2—N2	124.3 (3)	C20—C19—H19	121.0
C4—C3—C2	120.2 (3)	C18—C19—H19	121.0
C4—C3—H3	119.9	N6—C20—C19	124.7 (4)
C2—C3—H3	119.9	N6—C20—H20	117.7
C3—C4—C5	119.8 (3)	C19—C20—H20	117.7
C3—C4—H4	120.1	O4—Cl1—O1	109.0 (3)
C5—C4—H4	120.1	O4—Cl1—O3	109.4 (3)
N1—C5—C4	120.9 (3)	O1—Cl1—O3	108.6 (2)
N1—C5—H5	119.6	O4—Cl1—O2	111.8 (3)
C4—C5—H5	119.6	O1—Cl1—O2	107.7 (2)
N3—C6—N2	118.7 (3)	O3—Cl1—O2	110.3 (2)
N3—C6—C7	122.8 (3)	C22—O5—H5A	109.5
N2—C6—C7	118.5 (3)	C22—C21—H21A	109.5
C8—C7—C6	118.0 (4)	C22—C21—H21B	109.5
C8—C7—H7	121.0	H21A—C21—H21B	109.5
C6—C7—H7	121.0	C22—C21—H21C	109.5
C9—C8—C7	119.5 (4)	H21A—C21—H21C	109.5
C9—C8—H8	120.3	H21B—C21—H21C	109.5
C7—C8—H8	120.3	O5—C22—C21	118.1 (6)
C10—C9—C8	118.4 (4)	O5—C22—H22A	107.8
C10—C9—H9	120.8	C21—C22—H22A	107.8
C8—C9—H9	120.8	O5—C22—H22B	107.8
N3—C10—C9	124.2 (4)	C21—C22—H22B	107.8
N3—C10—H10	117.9	H22A—C22—H22B	107.1
C9—C10—H10	117.9

N1ⁱ—Ni1—N1—C1	−48.8 (2)	C6—C7—C8—C9	−1.2 (6)
N4—Ni1—N1—C1	130.6 (2)	C7—C8—C9—C10	1.0 (6)
N1ⁱ—Ni1—N1—C5	125.6 (3)	C6—N3—C10—C9	−1.8 (6)
N4—Ni1—N1—C5	−55.0 (3)	C8—C9—C10—N3	0.5 (6)
N1—Ni1—N4—C11	−59.8 (2)	C15—N4—C11—C12	−0.2 (4)
N4ⁱ—Ni1—N4—C11	120.8 (3)	Ni1—N4—C11—C12	175.7 (2)
N1—Ni1—N4—C15	116.0 (2)	N4—C11—C12—C13	−3.4 (4)
N4ⁱ—Ni1—N4—C15	−63.4 (2)	N4—C11—C12—N5	179.0 (3)
C5—N1—C1—C2	−1.2 (5)	C16—N5—C12—C13	25.5 (5)
Ni1—N1—C1—C2	173.2 (2)	C16—N5—C12—C11	−157.0 (3)
N1—C1—C2—C3	1.7 (5)	C11—C12—C13—C14	4.5 (4)
N1—C1—C2—N2	−179.5 (3)	N5—C12—C13—C14	−178.0 (3)
C6—N2—C2—C3	−157.8 (3)	C12—C13—C14—C15	−2.2 (5)
C6—N2—C2—C1	23.3 (6)	C11—N4—C15—C14	2.7 (4)
C1—C2—C3—C4	−0.9 (5)	Ni1—N4—C15—C14	−173.3 (2)
N2—C2—C3—C4	−179.9 (3)	C13—C14—C15—N4	−1.5 (5)
C2—C3—C4—C5	−0.2 (5)	C20—N6—C16—N5	−179.7 (3)
C1—N1—C5—C4	0.0 (5)	C20—N6—C16—C17	2.8 (5)
Ni1—N1—C5—C4	−174.4 (2)	C12—N5—C16—N6	7.6 (5)
C3—C4—C5—N1	0.6 (5)	C12—N5—C16—C17	−174.8 (3)
C10—N3—C6—N2	179.8 (3)	N6—C16—C17—C18	−1.5 (5)
C10—N3—C6—C7	1.5 (5)	N5—C16—C17—C18	−179.0 (3)
C2—N2—C6—N3	1.4 (6)	C16—C17—C18—C19	−0.9 (6)
C2—N2—C6—C7	179.8 (3)	C17—C18—C19—C20	1.8 (7)
N3—C6—C7—C8	−0.1 (6)	C16—N6—C20—C19	−1.9 (6)
N2—C6—C7—C8	−178.4 (3)	C18—C19—C20—N6	−0.4 (7)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O5	0.86	2.07	2.928 (5)	174
N2—H2···N6ⁱⁱ	0.86	2.27	3.129 (4)	176

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₉N₃)₄](ClO₄)₂·2C₂H₆O
M_r	1034.55
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	27.767 (4), 10.7067 (14), 18.144 (2)
β (°)	115.891 (9)
V (Å³)	4852.6 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.32 × 0.22 × 0.17

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.836, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	11042, 4315, 2875
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.134, 1.08
No. of reflections	4315
No. of parameters	314
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O5	0.86	2.07	2.928 (5)	174.0
N2—H2···N6ⁱ	0.86	2.27	3.129 (4)	176.3

Symmetry code: (i) x, y−1, z.

Acknowledgements

The author is grateful to Shuren University for financial support.

References

Biradha, K., Seward, C. M. & Zaworotko, J. (1999). Angew. Chem. Int. Ed. 1999, 38, 492–495. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Gudbjartson, H., Biradha, K., Poirier, K. & Zaworotko, M. J. (1999). J. Am. Chem. Soc. 121, 2599–2600. Web of Science CSD CrossRef CAS Google Scholar
Moulton, B. & Zaworotko, M. J. (2001). Chem. Rev. 101, 1629–1658. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su, C. Y., Cai, Y. P., Chen, C. L., Smith, M. D., Kaim, W. & Loye, H. C. (2003). J. Am. Chem. Soc. 125, 8595–8613. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhou, C. H., Wang, Y. Y., Li, D. S., Zhou, L. J., Liu, P. & Shi, Q. Z. (2006). Eur. J. Inorg. Chem. pp. 2437–2446. Web of Science CSD CrossRef Google Scholar

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Volume 64| Part 4| April 2008| Page m540

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Tetra­kis[3-(2-pyridylamino)pyridine-κN]nickel(II) diperchlorate ethanol disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Tetrakis[3-(2-pyridylamino)pyridine-κN]nickel(II) diperchlorate ethanol disolvate