Bis(tri-2-pyridyl­amine)­nickel(II) bis­(perchlorate)

Wang, S.; He, W.; Huang, W.

doi:10.1107/S1600536810051627

metal-organic compounds

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Volume 67| Part 1| January 2011| Page m78

https://doi.org/10.1107/S1600536810051627

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Bis(tri-2-pyridylamine)nickel(II) bis(perchlorate)

Shi Wang,^a ^* Wenrui He ^a and Wei Huang ^a

^aSchool of Materials Science & Engineering, Nanjing University of Posts and Telecommunications, Nanjing 210046, People's Republic of China
^*Correspondence e-mail: iamswang@njupt.edu.cn

(Received 30 November 2010; accepted 9 December 2010; online 15 December 2010)

In the title compound, [Ni(C₁₅H₁₂N₄)₂](ClO₄)₂, the Ni^II atom lies on an inversion center and is octahedrally coordinated by the N atoms of two tridentate tri-2-pyridylamine ligands. The two perchlorate anions are disordered over two sites with a refined occupancy ratio of 0.528 (19):0.472 (19).

Related literature

For background to luminescent coordination compounds, see: Liu et al. (1997 ). For related complexes, including the synthesis of 2,2′,2′′-tpa (tpa is tri-2-pyridylamine), see: Yang et al. (1999 ). For information on the use of 2,2′,2′′-tpa as a bidentate ligand, see: Wang et al. (2009 ).

Experimental

Crystal data

[Ni(C₁₅H₁₂N₄)₂](ClO₄)₂
M_r = 754.18
Monoclinic, P 2₁ /n
a = 8.360 (4) Å
b = 17.570 (8) Å
c = 11.165 (5) Å
β = 99.542 (5)°
V = 1617.3 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 296 K
0.22 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.861, T_max = 0.920
14055 measured reflections
3895 independent reflections
2611 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 1.03
3895 reflections
269 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.26 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: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051627/nk2079sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051627/nk2079Isup2.hkl

checkCIF report

Comment top

Luminescent organic and coordination compounds have been an active research area for decades because of their various potential applications in materials sciences. It has been demonstrated that 2,2'-dipyridylamine can produce a bright blue luminescence when deprotonated and bound to either an aluminium ion or a boron center (Liu et al., 1997). However, many of the previously reported aluminium or boron compounds based on 2,2'-dipyridylamine are not stable enough for electroluminescent devices. The neutral tripodal ligand 2,2',2''-tripyridylamine and its derivatives with Zn(II), Cd(II) and Hg(II) have been investigated for their optical properties (Yang et al., 1999). However, its complexes with d⁸ metal(II) remain unkown. By using the 2,2',2''-tripyridylamine ligand, we report here the synthesis and crystal structure of the title compound, bis(2,2',2''-tripyridylamine)nickel(II) bis(perchlorate), (I).

The structure of (I) consists of monomeric [Ni(2,2',2''-tpa)₂]²⁺ cations and associated ClO₄^- anions. The Ni atom lies on an inversion center. As shown in Fig. 1, the Ni center is six-coordinate with an octahedral geometry. In principle, 2,2',2''-tpa can function not only as a tridentate chelating ligand but also as a bidentate chelating ligand where only two pyridyl groups bind to the same central atom (Wang et al., 2009). In the title compound, each 2,2',2''-tpa ligand functions as a tridentate ligand, chelating to the nickel center. The two perchlorate anions are disordered over two sites with a refined occupancy ratio of 0.528 (19) : 0.472 (19).

Related literature top

For background to luminescent coordination compounds, see: Liu et al. (1997). For related complexes, including the synthesis of 2,2',2''-tpa, see: Yang et al. (1999). For information on the use of 2,2',2''-tpa as a bidentate ligand, see: Wang et al. (2009).

Experimental top

The ligand, 2,2',2''-tpa was synthesized according to the procedure described in the literature (Yang et al. (1999)).

A solution of 2,2',2''-tpa (62.11 mg, 0.2 mmol) in acetonitrile (5 ml) was added dropwise to a solution of Ni(ClO₄)₂.6H₂O (36.58 mg, 0.1 mmol) in acetonitrile (2 ml). The mixture was stirred at room temperature for 5 min and then filtered. Light purple crystals of (I) suitable for X-ray analysis were obtained by slow diffusion of filtrate.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), shown with 30% probability displacement ellipsoids. The disordered perchlorate anions and H atoms have been omitted for clarity. Unlabeled atoms are related to labeled atoms by inversion symmetry.

Bis(tri-2-pyridylamine)nickel(II) bis(perchlorate) top

Crystal data top

[Ni(C₁₅H₁₂N₄)₂](ClO₄)₂	F(000) = 772
M_r = 754.18	D_x = 1.549 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7662 reflections
a = 8.360 (4) Å	θ = 2.2–27.9°
b = 17.570 (8) Å	µ = 0.83 mm⁻¹
c = 11.165 (5) Å	T = 296 K
β = 99.542 (5)°	Block, purple
V = 1617.3 (13) Å³	0.22 × 0.15 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3895 independent reflections
Radiation source: fine-focus sealed tube	2611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 8.366 pixels mm^-1	θ_max = 28.4°, θ_min = 2.3°
phi and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −23→23
T_min = 0.861, T_max = 0.920	l = −14→14
14055 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0415P)² + 0.1545P] where P = (F_o² + 2F_c²)/3
3895 reflections	(Δ/σ)_max = 0.001
269 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₂N₄)₂](ClO₄)₂	V = 1617.3 (13) Å³
M_r = 754.18	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.360 (4) Å	µ = 0.83 mm⁻¹
b = 17.570 (8) Å	T = 296 K
c = 11.165 (5) Å	0.22 × 0.15 × 0.10 mm
β = 99.542 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3895 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2611 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.920	R_int = 0.040
14055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
3895 reflections	Δρ_min = −0.26 e Å⁻³
269 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Ni1	0.0000	0.0000	0.0000	0.03843 (14)
N1	0.1260 (2)	−0.05805 (10)	−0.21770 (15)	0.0415 (4)
N2	0.1529 (2)	−0.09211 (10)	−0.00942 (15)	0.0425 (4)
N3	−0.1341 (2)	−0.04164 (10)	−0.16286 (16)	0.0425 (5)
N4	0.1399 (2)	0.05822 (10)	−0.10841 (16)	0.0428 (4)
C1	0.1923 (3)	−0.10685 (12)	−0.11845 (19)	0.0398 (5)
C2	0.2910 (3)	−0.16666 (13)	−0.1379 (2)	0.0491 (6)
H2	0.3180	−0.1751	−0.2143	0.059*
C3	0.3487 (3)	−0.21360 (14)	−0.0420 (2)	0.0588 (7)
H3	0.4148	−0.2548	−0.0528	0.071*
C4	0.3080 (3)	−0.19915 (13)	0.0696 (2)	0.0546 (6)
H4	0.3456	−0.2305	0.1354	0.066*
C5	0.2114 (3)	−0.13810 (13)	0.0829 (2)	0.0496 (6)
H5	0.1852	−0.1281	0.1591	0.060*
C6	−0.0476 (3)	−0.06409 (12)	−0.24704 (19)	0.0414 (5)
C7	−0.1176 (3)	−0.09311 (14)	−0.3578 (2)	0.0547 (6)
H7	−0.0542	−0.1076	−0.4150	0.066*
C8	−0.2834 (4)	−0.10013 (15)	−0.3818 (2)	0.0647 (7)
H8	−0.3339	−0.1197	−0.4559	0.078*
C9	−0.3738 (3)	−0.07818 (14)	−0.2965 (2)	0.0577 (7)
H9	−0.4861	−0.0832	−0.3110	0.069*
C10	−0.2954 (3)	−0.04864 (14)	−0.1890 (2)	0.0533 (6)
H10	−0.3572	−0.0327	−0.1317	0.064*
C11	0.1900 (3)	0.13045 (13)	−0.0929 (2)	0.0492 (6)
H11	0.1612	0.1583	−0.0290	0.059*
C12	0.2822 (3)	0.16462 (14)	−0.1682 (2)	0.0575 (7)
H12	0.3156	0.2149	−0.1552	0.069*
C13	0.3246 (3)	0.12403 (16)	−0.2624 (2)	0.0627 (7)
H13	0.3886	0.1461	−0.3136	0.075*
C14	0.2716 (3)	0.05020 (14)	−0.2809 (2)	0.0527 (6)
H14	0.2970	0.0219	−0.3456	0.063*
C15	0.1808 (3)	0.01931 (12)	−0.20188 (19)	0.0402 (5)
Cl1	0.2377 (6)	0.3455 (4)	0.0694 (3)	0.0463 (11)	0.472 (19)
O1	0.1538 (19)	0.3916 (9)	0.1111 (12)	0.128 (5)	0.472 (19)
O2	0.224 (3)	0.2727 (6)	0.1240 (8)	0.153 (7)	0.472 (19)
O3	0.3932 (15)	0.3751 (8)	0.1296 (13)	0.129 (4)	0.472 (19)
O4	0.214 (2)	0.3370 (9)	−0.0534 (9)	0.140 (6)	0.472 (19)
Cl1'	0.2323 (10)	0.3362 (6)	0.0668 (6)	0.095 (2)	0.528 (19)
O1'	0.1418 (16)	0.4114 (7)	0.0767 (15)	0.133 (5)	0.528 (19)
O2'	0.1138 (18)	0.2869 (8)	0.0907 (17)	0.169 (5)	0.528 (19)
O3'	0.3760 (15)	0.3273 (15)	0.1348 (13)	0.205 (9)	0.528 (19)
O4'	0.2693 (18)	0.3279 (7)	−0.0504 (11)	0.109 (4)	0.528 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0488 (3)	0.0391 (2)	0.0291 (2)	0.00336 (19)	0.01177 (17)	−0.00443 (17)
N1	0.0529 (12)	0.0401 (10)	0.0331 (10)	0.0029 (9)	0.0114 (9)	−0.0027 (8)
N2	0.0543 (12)	0.0416 (10)	0.0319 (10)	0.0059 (9)	0.0082 (8)	−0.0038 (8)
N3	0.0476 (12)	0.0456 (11)	0.0343 (10)	0.0033 (9)	0.0069 (9)	−0.0043 (8)
N4	0.0525 (12)	0.0421 (10)	0.0355 (10)	−0.0008 (9)	0.0125 (9)	−0.0026 (8)
C1	0.0457 (13)	0.0387 (12)	0.0355 (11)	0.0002 (10)	0.0079 (10)	−0.0066 (9)
C2	0.0524 (15)	0.0475 (13)	0.0496 (14)	0.0036 (11)	0.0149 (12)	−0.0110 (11)
C3	0.0608 (17)	0.0466 (14)	0.0683 (17)	0.0154 (12)	0.0091 (14)	−0.0037 (13)
C4	0.0587 (16)	0.0474 (14)	0.0553 (15)	0.0077 (12)	0.0022 (13)	0.0065 (12)
C5	0.0603 (16)	0.0517 (14)	0.0369 (13)	0.0048 (12)	0.0080 (11)	0.0005 (11)
C6	0.0542 (15)	0.0386 (12)	0.0321 (11)	0.0019 (10)	0.0092 (10)	−0.0034 (9)
C7	0.0695 (18)	0.0591 (15)	0.0352 (13)	0.0035 (13)	0.0073 (12)	−0.0110 (11)
C8	0.075 (2)	0.0696 (18)	0.0440 (15)	−0.0041 (15)	−0.0063 (14)	−0.0125 (13)
C9	0.0534 (16)	0.0610 (16)	0.0549 (16)	−0.0016 (13)	−0.0021 (13)	−0.0030 (13)
C10	0.0530 (16)	0.0580 (15)	0.0489 (14)	0.0027 (12)	0.0082 (12)	−0.0058 (12)
C11	0.0578 (16)	0.0439 (13)	0.0462 (14)	−0.0016 (11)	0.0095 (12)	−0.0046 (11)
C12	0.0610 (17)	0.0502 (14)	0.0608 (17)	−0.0084 (13)	0.0091 (13)	0.0075 (13)
C13	0.0621 (17)	0.0682 (18)	0.0627 (17)	−0.0046 (14)	0.0242 (14)	0.0156 (14)
C14	0.0595 (16)	0.0600 (16)	0.0426 (14)	0.0065 (13)	0.0199 (12)	0.0062 (11)
C15	0.0434 (13)	0.0465 (13)	0.0317 (11)	0.0049 (10)	0.0095 (10)	0.0010 (9)
Cl1	0.046 (2)	0.072 (2)	0.0231 (16)	0.0105 (14)	0.0106 (12)	−0.0077 (12)
O1	0.158 (8)	0.140 (10)	0.099 (5)	0.080 (7)	0.058 (6)	0.001 (6)
O2	0.31 (2)	0.084 (6)	0.070 (5)	−0.006 (9)	0.037 (8)	0.018 (4)
O3	0.095 (6)	0.186 (10)	0.100 (6)	−0.052 (7)	0.000 (4)	−0.031 (6)
O4	0.195 (12)	0.199 (9)	0.023 (4)	0.091 (8)	0.013 (5)	−0.005 (4)
Cl1'	0.109 (4)	0.101 (3)	0.075 (3)	0.037 (3)	0.014 (3)	−0.020 (2)
O1'	0.107 (5)	0.070 (5)	0.211 (13)	0.027 (4)	−0.004 (6)	−0.036 (6)
O2'	0.169 (9)	0.122 (7)	0.251 (13)	0.007 (7)	0.139 (9)	0.013 (7)
O3'	0.086 (8)	0.36 (3)	0.148 (8)	0.120 (11)	−0.033 (7)	−0.089 (13)
O4'	0.144 (8)	0.120 (6)	0.080 (6)	−0.018 (6)	0.068 (6)	−0.032 (4)

Geometric parameters (Å, º) top

Ni1—N2	2.0755 (19)	C7—C8	1.373 (4)
Ni1—N2ⁱ	2.0755 (19)	C7—H7	0.9300
Ni1—N4	2.0851 (18)	C8—C9	1.367 (4)
Ni1—N4ⁱ	2.0851 (18)	C8—H8	0.9300
Ni1—N3ⁱ	2.1029 (19)	C9—C10	1.370 (3)
Ni1—N3	2.1029 (19)	C9—H9	0.9300
N1—C15	1.436 (3)	C10—H10	0.9300
N1—C1	1.437 (3)	C11—C12	1.370 (3)
N1—C6	1.438 (3)	C11—H11	0.9300
N2—C5	1.337 (3)	C12—C13	1.366 (4)
N2—C1	1.338 (3)	C12—H12	0.9300
N3—C6	1.337 (3)	C13—C14	1.375 (3)
N3—C10	1.337 (3)	C13—H13	0.9300
N4—C15	1.339 (3)	C14—C15	1.368 (3)
N4—C11	1.339 (3)	C14—H14	0.9300
C1—C2	1.375 (3)	Cl1—O1	1.212 (13)
C2—C3	1.374 (3)	Cl1—O4	1.361 (11)
C2—H2	0.9300	Cl1—O2	1.430 (13)
C3—C4	1.369 (3)	Cl1—O3	1.457 (12)
C3—H3	0.9300	Cl1'—O3'	1.320 (11)
C4—C5	1.366 (3)	Cl1'—O2'	1.375 (14)
C4—H4	0.9300	Cl1'—O4'	1.401 (11)
C5—H5	0.9300	Cl1'—O1'	1.537 (15)
C6—C7	1.375 (3)

N2—Ni1—N2ⁱ	180.0	N3—C6—C7	122.9 (2)
N2—Ni1—N4	86.78 (7)	N3—C6—N1	117.46 (18)
N2ⁱ—Ni1—N4	93.22 (7)	C7—C6—N1	119.7 (2)
N2—Ni1—N4ⁱ	93.22 (7)	C8—C7—C6	118.3 (2)
N2ⁱ—Ni1—N4ⁱ	86.78 (7)	C8—C7—H7	120.9
N4—Ni1—N4ⁱ	180.0	C6—C7—H7	120.9
N2—Ni1—N3ⁱ	94.05 (7)	C9—C8—C7	119.7 (2)
N2ⁱ—Ni1—N3ⁱ	85.95 (7)	C9—C8—H8	120.1
N4—Ni1—N3ⁱ	93.52 (8)	C7—C8—H8	120.1
N4ⁱ—Ni1—N3ⁱ	86.48 (8)	C8—C9—C10	118.5 (3)
N2—Ni1—N3	85.95 (7)	C8—C9—H9	120.7
N2ⁱ—Ni1—N3	94.05 (7)	C10—C9—H9	120.7
N4—Ni1—N3	86.48 (8)	N3—C10—C9	123.0 (2)
N4ⁱ—Ni1—N3	93.52 (8)	N3—C10—H10	118.5
N3ⁱ—Ni1—N3	180.0	C9—C10—H10	118.5
C15—N1—C1	113.30 (17)	N4—C11—C12	122.2 (2)
C15—N1—C6	112.77 (17)	N4—C11—H11	118.9
C1—N1—C6	112.15 (17)	C12—C11—H11	118.9
C5—N2—C1	118.06 (19)	C13—C12—C11	119.2 (2)
C5—N2—Ni1	125.59 (15)	C13—C12—H12	120.4
C1—N2—Ni1	116.34 (14)	C11—C12—H12	120.4
C6—N3—C10	117.54 (19)	C12—C13—C14	119.3 (2)
C6—N3—Ni1	115.96 (15)	C12—C13—H13	120.3
C10—N3—Ni1	126.49 (15)	C14—C13—H13	120.3
C15—N4—C11	118.01 (19)	C15—C14—C13	118.5 (2)
C15—N4—Ni1	116.26 (15)	C15—C14—H14	120.8
C11—N4—Ni1	125.72 (15)	C13—C14—H14	120.8
N2—C1—C2	122.4 (2)	N4—C15—C14	122.8 (2)
N2—C1—N1	117.66 (18)	N4—C15—N1	117.50 (18)
C2—C1—N1	119.90 (19)	C14—C15—N1	119.74 (19)
C3—C2—C1	118.5 (2)	O1—Cl1—O4	117.6 (10)
C3—C2—H2	120.7	O1—Cl1—O2	109.8 (9)
C1—C2—H2	120.7	O4—Cl1—O2	108.8 (9)
C4—C3—C2	119.3 (2)	O1—Cl1—O3	96.5 (10)
C4—C3—H3	120.3	O4—Cl1—O3	118.3 (10)
C2—C3—H3	120.3	O2—Cl1—O3	104.7 (9)
C5—C4—C3	119.0 (2)	O3'—Cl1'—O2'	115.5 (11)
C5—C4—H4	120.5	O3'—Cl1'—O4'	101.8 (10)
C3—C4—H4	120.5	O2'—Cl1'—O4'	113.2 (9)
N2—C5—C4	122.6 (2)	O3'—Cl1'—O1'	118.1 (12)
N2—C5—H5	118.7	O2'—Cl1'—O1'	98.6 (8)
C4—C5—H5	118.7	O4'—Cl1'—O1'	110.1 (9)

N4—Ni1—N2—C5	138.49 (19)	C2—C3—C4—C5	−0.3 (4)
N4ⁱ—Ni1—N2—C5	−41.51 (19)	C1—N2—C5—C4	−0.4 (3)
N3ⁱ—Ni1—N2—C5	45.18 (19)	Ni1—N2—C5—C4	178.09 (17)
N3—Ni1—N2—C5	−134.82 (19)	C3—C4—C5—N2	0.9 (4)
N4—Ni1—N2—C1	−42.98 (16)	C10—N3—C6—C7	0.4 (3)
N4ⁱ—Ni1—N2—C1	137.02 (16)	Ni1—N3—C6—C7	179.54 (18)
N3ⁱ—Ni1—N2—C1	−136.29 (16)	C10—N3—C6—N1	−178.68 (19)
N3—Ni1—N2—C1	43.71 (16)	Ni1—N3—C6—N1	0.4 (2)
N2—Ni1—N3—C6	−44.10 (16)	C15—N1—C6—N3	−65.0 (2)
N2ⁱ—Ni1—N3—C6	135.90 (16)	C1—N1—C6—N3	64.4 (2)
N4—Ni1—N3—C6	42.92 (16)	C15—N1—C6—C7	115.9 (2)
N4ⁱ—Ni1—N3—C6	−137.08 (16)	C1—N1—C6—C7	−114.8 (2)
N2—Ni1—N3—C10	134.9 (2)	N3—C6—C7—C8	−0.9 (4)
N2ⁱ—Ni1—N3—C10	−45.1 (2)	N1—C6—C7—C8	178.2 (2)
N4—Ni1—N3—C10	−138.1 (2)	C6—C7—C8—C9	0.2 (4)
N4ⁱ—Ni1—N3—C10	41.9 (2)	C7—C8—C9—C10	0.8 (4)
N2—Ni1—N4—C15	43.27 (16)	C6—N3—C10—C9	0.7 (3)
N2ⁱ—Ni1—N4—C15	−136.73 (16)	Ni1—N3—C10—C9	−178.30 (18)
N3ⁱ—Ni1—N4—C15	137.13 (16)	C8—C9—C10—N3	−1.3 (4)
N3—Ni1—N4—C15	−42.87 (16)	C15—N4—C11—C12	−0.8 (3)
N2—Ni1—N4—C11	−137.4 (2)	Ni1—N4—C11—C12	179.82 (18)
N2ⁱ—Ni1—N4—C11	42.6 (2)	N4—C11—C12—C13	0.1 (4)
N3ⁱ—Ni1—N4—C11	−43.5 (2)	C11—C12—C13—C14	1.0 (4)
N3—Ni1—N4—C11	136.5 (2)	C12—C13—C14—C15	−1.5 (4)
C5—N2—C1—C2	−0.6 (3)	C11—N4—C15—C14	0.3 (3)
Ni1—N2—C1—C2	−179.22 (17)	Ni1—N4—C15—C14	179.77 (18)
C5—N2—C1—N1	178.7 (2)	C11—N4—C15—N1	−179.87 (19)
Ni1—N2—C1—N1	0.1 (3)	Ni1—N4—C15—N1	−0.4 (3)
C15—N1—C1—N2	64.0 (3)	C13—C14—C15—N4	0.8 (4)
C6—N1—C1—N2	−65.1 (2)	C13—C14—C15—N1	−179.0 (2)
C15—N1—C1—C2	−116.7 (2)	C1—N1—C15—N4	−63.5 (3)
C6—N1—C1—C2	114.2 (2)	C6—N1—C15—N4	65.3 (2)
N2—C1—C2—C3	1.1 (3)	C1—N1—C15—C14	116.3 (2)
N1—C1—C2—C3	−178.2 (2)	C6—N1—C15—C14	−115.0 (2)
C1—C2—C3—C4	−0.6 (4)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₂N₄)₂](ClO₄)₂
M_r	754.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.360 (4), 17.570 (8), 11.165 (5)
β (°)	99.542 (5)
V (Å³)	1617.3 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.22 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.861, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	14055, 3895, 2611
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 1.03
No. of reflections	3895
No. of parameters	269
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.26

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by NY208044, BK2010527 and in part by the National Basic Research Program of China (2009CB930601).

References

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Liu, W., Hassan, A. & Wang, S. (1997). Organometallics, 16, 4257–4259. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). 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
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