Bis(nitrato-κ2O,O′)bis­[N-(triphenyl­meth­yl)pyridin-2-amine-κN1]nickel(II)

Zhang, G.-N.; Jiang, C.

doi:10.1107/S1600536810044624

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1521

https://doi.org/10.1107/S1600536810044624

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Bis(nitrato-κ²O,O′)bis[N-(triphenylmethyl)pyridin-2-amine-κN¹]nickel(II)

Guang-Ning Zhang ^a and Chunjie Jiang ^a ^*

^aInstitute of Chemistry for Functionalized Materials, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: zgn25721086@163.com

(Received 12 October 2010; accepted 1 November 2010; online 6 November 2010)

In the title compound, [Ni(NO₃)₂(C₂₄H₂₀N₂)₂], the Ni^II atom has a distorted pseudo-octahedral coordination geometry defined by two chelating nitrate groups and two pyridine N atoms of the monodentate N-(triphenylmethyl)pyridin-2-amine ligands. Intramolecular N—H⋯O hydrogen bonds help to establish the configuration.

Related literature

For the isostructural dichlorido-cobalt(II), -zinc(II) and -cadmium(II) complexes with bis{2-[(triphenylmethyl)amino]pyridyl} ligands, see: Fang et al. (2006 ); Zhang et al. (2007 ) and Zhang (2008 ), respectively.

Experimental

Crystal data

[Ni(NO₃)₂(C₂₄H₂₀N₂)₂]
M_r = 855.57
Monoclinic, P 2₁ /n
a = 10.287 (2) Å
b = 23.462 (5) Å
c = 17.868 (4) Å
β = 105.266 (3)°
V = 4160.3 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 293 K
0.53 × 0.52 × 0.47 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.733, T_max = 0.791
20535 measured reflections
7279 independent reflections
4928 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.01
7279 reflections
550 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O5	2.050 (2)
Ni1—O2	2.0607 (19)
Ni1—N3	2.061 (2)
Ni1—N4	2.062 (2)
Ni1—O4	2.133 (2)
Ni1—O1	2.150 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5B⋯O2	0.86	2.16	2.994 (3)	165
N6—H6A⋯O5	0.86	2.22	3.048 (3)	162

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810044624/si2301sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044624/si2301Isup2.hkl

checkCIF report

Comment top

The first example of a distorted tetrahedral metalorganic title related complex, dichloridobis{2-[(triphenylmethyl)amino]pyridyl}cobalt(II), was reported by Fang et al. (2006). We continued the study by replacement of cobalt(II) with zinc(II) (Zhang et al., 2007) and cadmium(II) (Zhang, 2008) as the coordination centre. For the title complex we used two nitrato instead of chlorido ligands in order to study the geometric and packing differences for this structure type.

The molecular structure of (I) is shown in Fig.1. In the title compound, the Ni1 atom is distorted pseudo-tetrahedral coordinated by pyridyl atoms N3, N4 and two pairs of nitrato oxygen atoms O1/O2 and O4/O5 (Table 1). The O1—Ni1—O5 and O2—Ni1—O4 angles are observed: 94.26 (9)° and 91.56 (9)°. These two angles are less than the Cl—Co—Cl, Cl—Zn—Cl and Cl—Cd—Cl angles in the literature (121.18 (3)° for Cl-Cd–Cl). The large volume of the two 2-[N-(triphenylmethyl)imino]pyridyl ligands determine the crystal packing of the Ni(II) title complex and related dichlorido-Co(II) (Fang et al., 2006), dichlorido-Zn(II) (Zhang et al., 2007) and dichlorido-Cd(II) (Zhang, 2008) structures. The four compounds crystallize in the monoclinic space group P2₁/n and exhibit similar unit-cell parameters. Packing motifs of unit cell projections down the a axis are shown in Zhang et al. (2007) and Zhang (2008) for this structure type. Intramolecular N—H···O hydrogen bonds help to establish the conformation of the title complex (Table 2). Similar properties are observed with N—H···Cl hydrogen bonds in the dichlorido complexes.

Related literature top

For the isostructural dichlorido-cobalt(II), -zinc(II) and -cadmium(II) complexes with bis{2-[(triphenylmethyl)amino]pyridyl} ligands, see: Fang et al. (2006); Zhang et al. (2007) and Zhang (2008), respectively.

Experimental top

2-[N-(triphenylmethyl)imino]pyridyl ligand (0.03 g, 0.09 mmol) and Ni(NO₃) ₂(0.025 g, 0.14 mmol) were dissolved in 5 ml and 10 ml of ethanol respectively, then mixed. The mixed solution was stirred about 30 minutes and covered with hexane (10 ml). After two months, blue crystals were obtained.

Structure description top

For the isostructural dichlorido-cobalt(II), -zinc(II) and -cadmium(II) complexes with bis{2-[(triphenylmethyl)amino]pyridyl} ligands, see: Fang et al. (2006); Zhang et al. (2007) and Zhang (2008), respectively.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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: SHELXL97 (Sheldrick, 2008.

Figures top

Fig. 1. Molecular structure of (I), showing displacement ellipsids at the 30% probability level. H atoms have been omitted.

Bis(nitrato-κ²O,O')bis[N-(triphenylmethyl)pyridin- 2-amine-κN¹]nickel(II) top

Crystal data top

[Ni(NO₃)₂(C₂₄H₂₀N₂)₂]	F(000) = 1784
M_r = 855.57	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.287 (2) Å	Cell parameters from 3946 reflections
b = 23.462 (5) Å	θ = 2.2–21.3°
c = 17.868 (4) Å	µ = 0.53 mm⁻¹
β = 105.266 (3)°	T = 293 K
V = 4160.3 (14) Å³	Plate, blue
Z = 4	0.53 × 0.52 × 0.47 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	7279 independent reflections
Radiation source: fine-focus sealed tube	4928 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
CCD scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→12
T_min = 0.733, T_max = 0.791	k = −27→27
20535 measured reflections	l = −19→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0524P)² + 0.5431P] where P = (F_o² + 2F_c²)/3
7279 reflections	(Δ/σ)_max = 0.001
550 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ni(NO₃)₂(C₂₄H₂₀N₂)₂]	V = 4160.3 (14) Å³
M_r = 855.57	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.287 (2) Å	µ = 0.53 mm⁻¹
b = 23.462 (5) Å	T = 293 K
c = 17.868 (4) Å	0.53 × 0.52 × 0.47 mm
β = 105.266 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7279 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4928 reflections with I > 2σ(I)
T_min = 0.733, T_max = 0.791	R_int = 0.041
20535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	Δρ_max = 0.29 e Å⁻³
7279 reflections	Δρ_min = −0.30 e Å⁻³
550 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	0.68497 (3)	0.181447 (15)	0.17328 (2)	0.04318 (13)
O1	0.7259 (2)	0.21664 (10)	0.07075 (13)	0.0656 (6)
O2	0.83125 (19)	0.24336 (8)	0.18590 (12)	0.0556 (5)
O3	0.8942 (3)	0.27540 (12)	0.08652 (16)	0.0931 (9)
O4	0.8238 (2)	0.11640 (10)	0.16253 (14)	0.0660 (6)
O5	0.6099 (2)	0.10632 (8)	0.12069 (11)	0.0545 (5)
O6	0.7416 (3)	0.03988 (11)	0.09769 (16)	0.0996 (9)
C1	0.4878 (3)	0.27695 (11)	0.18500 (15)	0.0393 (6)
C2	0.3571 (3)	0.29778 (12)	0.17711 (17)	0.0475 (7)
H2A	0.3441	0.3316	0.2012	0.057*
C3	0.2494 (3)	0.26823 (13)	0.13411 (18)	0.0530 (8)
H3A	0.1626	0.2819	0.1289	0.064*
C4	0.2688 (3)	0.21793 (13)	0.09802 (18)	0.0571 (8)
H4A	0.1964	0.1979	0.0669	0.068*
C5	0.3968 (3)	0.19888 (13)	0.10973 (17)	0.0526 (8)
H5A	0.4102	0.1649	0.0860	0.063*
C6	0.6152 (3)	0.13579 (11)	0.32002 (16)	0.0404 (6)
C7	0.6306 (3)	0.13566 (13)	0.39981 (16)	0.0492 (7)
H7A	0.5686	0.1167	0.4204	0.059*
C8	0.7370 (3)	0.16348 (14)	0.44772 (18)	0.0570 (8)
H8A	0.7476	0.1634	0.5010	0.068*
C9	0.8285 (3)	0.19170 (14)	0.41694 (19)	0.0636 (9)
H9A	0.9024	0.2103	0.4488	0.076*
C10	0.8075 (3)	0.19145 (13)	0.33879 (17)	0.0541 (8)
H10A	0.8692	0.2106	0.3181	0.065*
C11	0.6099 (3)	0.35901 (11)	0.26601 (16)	0.0413 (7)
C12	0.3994 (3)	0.07672 (11)	0.28363 (15)	0.0407 (7)
C13	0.5717 (3)	0.41085 (12)	0.21192 (17)	0.0453 (7)
C14	0.5979 (3)	0.46533 (13)	0.2424 (2)	0.0597 (8)
H14A	0.6378	0.4699	0.2952	0.072*
C15	0.5654 (4)	0.51291 (15)	0.1954 (2)	0.0732 (10)
H15A	0.5829	0.5492	0.2167	0.088*
C16	0.5082 (4)	0.50679 (18)	0.1184 (3)	0.0794 (11)
H16A	0.4854	0.5389	0.0871	0.095*
C17	0.4839 (4)	0.45370 (18)	0.0866 (2)	0.0762 (11)
H17A	0.4452	0.4497	0.0337	0.091*
C18	0.5166 (3)	0.40572 (14)	0.13285 (19)	0.0586 (8)
H18A	0.5013	0.3697	0.1105	0.070*
C19	0.5259 (3)	0.35298 (12)	0.32558 (16)	0.0413 (7)
N1	0.8190 (3)	0.24611 (12)	0.11230 (18)	0.0611 (7)
N2	0.7279 (3)	0.08570 (13)	0.12585 (16)	0.0633 (7)
N3	0.5067 (2)	0.22612 (9)	0.15372 (12)	0.0408 (5)
N4	0.7028 (2)	0.16517 (9)	0.28896 (13)	0.0411 (5)
N5	0.6013 (2)	0.30583 (9)	0.22205 (13)	0.0428 (6)
H5B	0.6765	0.2912	0.2193	0.051*
N6	0.5169 (2)	0.10664 (9)	0.26913 (13)	0.0425 (6)
H6A	0.5236	0.1054	0.2222	0.051*
C20	0.4470 (3)	0.39598 (13)	0.34225 (18)	0.0525 (8)
H20A	0.4366	0.4298	0.3142	0.063*
C21	0.3834 (3)	0.38893 (16)	0.4007 (2)	0.0714 (10)
H21A	0.3313	0.4184	0.4121	0.086*
C22	0.3957 (3)	0.33925 (16)	0.4420 (2)	0.0686 (10)
H22A	0.3525	0.3350	0.4813	0.082*
C23	0.4724 (3)	0.29587 (15)	0.42496 (18)	0.0589 (8)
H23A	0.4811	0.2619	0.4526	0.071*
C24	0.5366 (3)	0.30271 (12)	0.36678 (17)	0.0484 (7)
H24A	0.5879	0.2730	0.3552	0.058*
C25	0.7599 (3)	0.36597 (12)	0.31007 (17)	0.0451 (7)
C26	0.8008 (3)	0.37622 (16)	0.3884 (2)	0.0721 (10)
H26A	0.7371	0.3781	0.4168	0.087*
C27	0.9352 (4)	0.3837 (2)	0.4253 (2)	0.1057 (16)
H27A	0.9614	0.3917	0.4781	0.127*
C28	1.0291 (4)	0.3796 (2)	0.3850 (3)	0.1009 (15)
H28A	1.1200	0.3828	0.4106	0.121*
C29	0.9910 (4)	0.37064 (17)	0.3065 (3)	0.0862 (12)
H29A	1.0556	0.3685	0.2787	0.103*
C30	0.8563 (3)	0.36475 (13)	0.2689 (2)	0.0624 (9)
H30A	0.8301	0.3599	0.2153	0.075*
C31	0.3252 (3)	0.11809 (12)	0.32560 (16)	0.0422 (7)
C32	0.2881 (3)	0.10467 (13)	0.39223 (18)	0.0539 (8)
H32A	0.3092	0.0690	0.4149	0.065*
C33	0.2197 (3)	0.14399 (15)	0.4256 (2)	0.0660 (9)
H33A	0.1953	0.1344	0.4706	0.079*
C34	0.1878 (3)	0.19659 (15)	0.3933 (2)	0.0644 (9)
H34A	0.1416	0.2227	0.4160	0.077*
C35	0.2242 (3)	0.21059 (14)	0.3277 (2)	0.0647 (9)
H35A	0.2023	0.2462	0.3051	0.078*
C36	0.2935 (3)	0.17186 (13)	0.29476 (19)	0.0554 (8)
H36A	0.3196	0.1822	0.2506	0.066*
C37	0.3108 (3)	0.06214 (11)	0.20148 (16)	0.0426 (7)
C38	0.1758 (3)	0.07570 (13)	0.17557 (18)	0.0530 (8)
H38A	0.1325	0.0930	0.2091	0.064*
C39	0.1050 (3)	0.06387 (15)	0.1007 (2)	0.0650 (9)
H39A	0.0138	0.0728	0.0842	0.078*
C40	0.1669 (4)	0.03915 (14)	0.0502 (2)	0.0655 (9)
H40A	0.1193	0.0328	−0.0011	0.079*
C41	0.2990 (3)	0.02375 (13)	0.07534 (19)	0.0612 (9)
H41A	0.3414	0.0064	0.0413	0.073*
C42	0.3699 (3)	0.03371 (12)	0.15082 (17)	0.0519 (8)
H42A	0.4586	0.0212	0.1682	0.062*
C43	0.4392 (3)	0.02037 (11)	0.32687 (16)	0.0423 (7)
C44	0.3388 (3)	−0.01635 (13)	0.33673 (17)	0.0530 (8)
H44A	0.2488	−0.0065	0.3165	0.064*
C45	0.3707 (4)	−0.06708 (14)	0.3760 (2)	0.0665 (9)
H45A	0.3021	−0.0906	0.3829	0.080*
C46	0.5015 (4)	−0.08334 (15)	0.4049 (2)	0.0716 (10)
H46A	0.5225	−0.1173	0.4321	0.086*
C47	0.6017 (4)	−0.04883 (15)	0.3930 (2)	0.0705 (10)
H47A	0.6912	−0.0599	0.4114	0.085*
C48	0.5707 (3)	0.00223 (13)	0.35413 (18)	0.0562 (8)
H48A	0.6399	0.0249	0.3461	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0444 (2)	0.0463 (2)	0.0411 (2)	−0.00194 (17)	0.01515 (17)	−0.00311 (17)
O1	0.0695 (15)	0.0810 (16)	0.0498 (14)	−0.0109 (13)	0.0223 (12)	−0.0027 (12)
O2	0.0553 (13)	0.0595 (13)	0.0568 (15)	−0.0055 (10)	0.0233 (11)	−0.0067 (11)
O3	0.098 (2)	0.099 (2)	0.099 (2)	−0.0251 (16)	0.0539 (17)	0.0166 (16)
O4	0.0573 (14)	0.0686 (15)	0.0732 (16)	0.0058 (12)	0.0190 (12)	−0.0129 (13)
O5	0.0578 (14)	0.0532 (13)	0.0527 (13)	−0.0010 (11)	0.0152 (11)	−0.0071 (10)
O6	0.128 (2)	0.0669 (17)	0.102 (2)	0.0222 (16)	0.0274 (17)	−0.0336 (16)
C1	0.0405 (16)	0.0413 (16)	0.0351 (16)	−0.0014 (13)	0.0085 (13)	0.0023 (13)
C2	0.0410 (18)	0.0467 (17)	0.0522 (19)	0.0032 (14)	0.0077 (14)	0.0053 (14)
C3	0.0402 (18)	0.059 (2)	0.054 (2)	0.0035 (15)	0.0021 (14)	0.0142 (16)
C4	0.049 (2)	0.056 (2)	0.054 (2)	−0.0098 (16)	−0.0073 (15)	0.0042 (16)
C5	0.054 (2)	0.0521 (19)	0.0468 (19)	−0.0041 (15)	0.0043 (15)	−0.0056 (15)
C6	0.0386 (16)	0.0419 (16)	0.0406 (17)	0.0023 (13)	0.0104 (13)	−0.0033 (13)
C7	0.0486 (18)	0.0594 (19)	0.0399 (18)	−0.0063 (15)	0.0124 (14)	−0.0010 (15)
C8	0.057 (2)	0.073 (2)	0.0378 (18)	−0.0028 (17)	0.0073 (15)	−0.0057 (16)
C9	0.051 (2)	0.086 (3)	0.047 (2)	−0.0190 (17)	0.0004 (15)	−0.0067 (17)
C10	0.0410 (17)	0.071 (2)	0.049 (2)	−0.0131 (15)	0.0099 (15)	−0.0019 (16)
C11	0.0383 (16)	0.0398 (16)	0.0454 (17)	−0.0019 (12)	0.0101 (13)	−0.0033 (13)
C12	0.0421 (16)	0.0418 (16)	0.0397 (16)	−0.0035 (13)	0.0132 (13)	−0.0011 (13)
C13	0.0384 (16)	0.0505 (18)	0.0488 (19)	0.0000 (13)	0.0144 (14)	0.0034 (15)
C14	0.070 (2)	0.048 (2)	0.061 (2)	0.0015 (16)	0.0172 (17)	0.0029 (17)
C15	0.084 (3)	0.050 (2)	0.096 (3)	0.0018 (18)	0.043 (2)	0.010 (2)
C16	0.085 (3)	0.068 (3)	0.095 (3)	0.018 (2)	0.042 (2)	0.034 (2)
C17	0.080 (3)	0.091 (3)	0.057 (2)	0.001 (2)	0.0185 (19)	0.027 (2)
C18	0.061 (2)	0.060 (2)	0.057 (2)	−0.0063 (16)	0.0188 (17)	0.0061 (17)
C19	0.0325 (15)	0.0474 (17)	0.0432 (17)	−0.0051 (13)	0.0087 (12)	−0.0058 (14)
N1	0.0648 (19)	0.0613 (18)	0.066 (2)	−0.0014 (15)	0.0325 (16)	0.0043 (15)
N2	0.078 (2)	0.0576 (19)	0.0553 (18)	0.0114 (17)	0.0187 (16)	−0.0052 (15)
N3	0.0425 (14)	0.0441 (14)	0.0345 (13)	−0.0003 (11)	0.0080 (11)	−0.0007 (11)
N4	0.0339 (13)	0.0483 (14)	0.0403 (14)	−0.0022 (10)	0.0085 (11)	−0.0015 (11)
N5	0.0343 (13)	0.0444 (14)	0.0501 (15)	0.0017 (10)	0.0116 (11)	−0.0081 (11)
N6	0.0426 (13)	0.0522 (14)	0.0340 (13)	−0.0088 (11)	0.0125 (11)	−0.0026 (11)
C20	0.0459 (18)	0.0470 (18)	0.069 (2)	−0.0013 (14)	0.0224 (16)	−0.0036 (15)
C21	0.058 (2)	0.066 (2)	0.103 (3)	−0.0010 (18)	0.044 (2)	−0.016 (2)
C22	0.062 (2)	0.084 (3)	0.072 (2)	−0.017 (2)	0.0383 (19)	−0.011 (2)
C23	0.0515 (19)	0.069 (2)	0.056 (2)	−0.0105 (17)	0.0125 (16)	0.0095 (17)
C24	0.0420 (17)	0.0520 (19)	0.0526 (19)	0.0002 (14)	0.0149 (14)	0.0020 (15)
C25	0.0407 (16)	0.0427 (17)	0.0506 (19)	−0.0059 (13)	0.0098 (14)	0.0013 (14)
C26	0.050 (2)	0.108 (3)	0.053 (2)	−0.0233 (19)	0.0054 (16)	0.004 (2)
C27	0.065 (3)	0.168 (5)	0.070 (3)	−0.044 (3)	−0.007 (2)	0.021 (3)
C28	0.042 (2)	0.139 (4)	0.107 (4)	−0.023 (2)	−0.005 (2)	0.023 (3)
C29	0.048 (2)	0.101 (3)	0.115 (4)	−0.017 (2)	0.030 (2)	−0.011 (3)
C30	0.0460 (19)	0.069 (2)	0.075 (2)	−0.0109 (16)	0.0199 (17)	−0.0081 (18)
C31	0.0402 (16)	0.0474 (17)	0.0379 (16)	−0.0058 (13)	0.0084 (13)	−0.0039 (14)
C32	0.0589 (19)	0.0527 (19)	0.053 (2)	0.0003 (15)	0.0193 (16)	0.0007 (15)
C33	0.070 (2)	0.077 (3)	0.059 (2)	−0.0062 (19)	0.0326 (18)	−0.0098 (19)
C34	0.058 (2)	0.061 (2)	0.080 (3)	−0.0018 (17)	0.0297 (19)	−0.0191 (19)
C35	0.066 (2)	0.050 (2)	0.079 (3)	0.0017 (17)	0.0206 (19)	−0.0037 (18)
C36	0.064 (2)	0.051 (2)	0.055 (2)	−0.0001 (16)	0.0232 (16)	−0.0024 (15)
C37	0.0432 (17)	0.0407 (16)	0.0442 (17)	−0.0090 (13)	0.0122 (13)	0.0029 (13)
C38	0.0500 (19)	0.0558 (19)	0.052 (2)	−0.0069 (15)	0.0112 (15)	−0.0018 (15)
C39	0.048 (2)	0.072 (2)	0.065 (2)	−0.0051 (17)	−0.0020 (17)	−0.0020 (19)
C40	0.073 (3)	0.068 (2)	0.047 (2)	−0.0184 (19)	0.0016 (18)	−0.0012 (17)
C41	0.068 (2)	0.061 (2)	0.057 (2)	−0.0164 (18)	0.0189 (18)	−0.0173 (17)
C42	0.0513 (19)	0.0510 (19)	0.052 (2)	−0.0061 (15)	0.0119 (15)	−0.0088 (15)
C43	0.0446 (18)	0.0426 (16)	0.0407 (16)	−0.0005 (13)	0.0128 (13)	0.0014 (13)
C44	0.0511 (19)	0.0503 (19)	0.057 (2)	−0.0014 (15)	0.0133 (15)	0.0083 (16)
C45	0.081 (3)	0.049 (2)	0.073 (2)	−0.0089 (18)	0.026 (2)	0.0060 (18)
C46	0.088 (3)	0.051 (2)	0.072 (3)	0.010 (2)	0.015 (2)	0.0142 (18)
C47	0.067 (2)	0.060 (2)	0.081 (3)	0.0165 (19)	0.0123 (19)	0.0123 (19)
C48	0.052 (2)	0.055 (2)	0.063 (2)	−0.0017 (16)	0.0175 (16)	−0.0007 (16)

Geometric parameters (Å, º) top

Ni1—O5	2.050 (2)	N5—H5B	0.8600
Ni1—O2	2.0607 (19)	N6—H6A	0.8600
Ni1—N3	2.061 (2)	C20—C21	1.380 (4)
Ni1—N4	2.062 (2)	C20—H20A	0.9300
Ni1—O4	2.133 (2)	C21—C22	1.368 (5)
Ni1—O1	2.150 (2)	C21—H21A	0.9300
O1—N1	1.254 (3)	C22—C23	1.370 (4)
O2—N1	1.289 (3)	C22—H22A	0.9300
O3—N1	1.213 (3)	C23—C24	1.380 (4)
O4—N2	1.258 (3)	C23—H23A	0.9300
O5—N2	1.287 (3)	C24—H24A	0.9300
O6—N2	1.211 (3)	C25—C26	1.372 (4)
C1—N3	1.353 (3)	C25—C30	1.382 (4)
C1—N5	1.361 (3)	C26—C27	1.377 (5)
C1—C2	1.403 (3)	C26—H26A	0.9300
C2—C3	1.360 (4)	C27—C28	1.353 (6)
C2—H2A	0.9300	C27—H27A	0.9300
C3—C4	1.384 (4)	C28—C29	1.369 (6)
C3—H3A	0.9300	C28—H28A	0.9300
C4—C5	1.354 (4)	C29—C30	1.379 (5)
C4—H4A	0.9300	C29—H29A	0.9300
C5—N3	1.355 (3)	C30—H30A	0.9300
C5—H5A	0.9300	C31—C32	1.379 (4)
C6—N6	1.354 (3)	C31—C36	1.381 (4)
C6—N4	1.363 (3)	C32—C33	1.387 (4)
C6—C7	1.392 (4)	C32—H32A	0.9300
C7—C8	1.365 (4)	C33—C34	1.365 (5)
C7—H7A	0.9300	C33—H33A	0.9300
C8—C9	1.379 (4)	C34—C35	1.362 (5)
C8—H8A	0.9300	C34—H34A	0.9300
C9—C10	1.356 (4)	C35—C36	1.379 (4)
C9—H9A	0.9300	C35—H35A	0.9300
C10—N4	1.352 (3)	C36—H36A	0.9300
C10—H10A	0.9300	C37—C38	1.380 (4)
C11—N5	1.464 (3)	C37—C42	1.387 (4)
C11—C13	1.539 (4)	C38—C39	1.373 (4)
C11—C19	1.545 (4)	C38—H38A	0.9300
C11—C25	1.545 (4)	C39—C40	1.363 (5)
C12—N6	1.478 (3)	C39—H39A	0.9300
C12—C43	1.532 (4)	C40—C41	1.363 (4)
C12—C31	1.546 (4)	C40—H40A	0.9300
C12—C37	1.549 (4)	C41—C42	1.374 (4)
C13—C18	1.382 (4)	C41—H41A	0.9300
C13—C14	1.388 (4)	C42—H42A	0.9300
C14—C15	1.384 (4)	C43—C48	1.379 (4)
C14—H14A	0.9300	C43—C44	1.391 (4)
C15—C16	1.354 (5)	C44—C45	1.377 (4)
C15—H15A	0.9300	C44—H44A	0.9300
C16—C17	1.364 (5)	C45—C46	1.362 (5)
C16—H16A	0.9300	C45—H45A	0.9300
C17—C18	1.384 (4)	C46—C47	1.370 (5)
C17—H17A	0.9300	C46—H46A	0.9300
C18—H18A	0.9300	C47—C48	1.380 (4)
C19—C20	1.375 (4)	C47—H47A	0.9300
C19—C24	1.379 (4)	C48—H48A	0.9300

O5—Ni1—O2	146.32 (8)	C1—N5—C11	127.5 (2)
O5—Ni1—N3	98.53 (9)	C1—N5—H5B	116.3
O2—Ni1—N3	104.58 (8)	C11—N5—H5B	116.3
O5—Ni1—N4	102.92 (8)	C6—N6—C12	128.5 (2)
O2—Ni1—N4	98.69 (9)	C6—N6—H6A	115.7
N3—Ni1—N4	96.00 (8)	C12—N6—H6A	115.7
O5—Ni1—O4	61.58 (8)	C19—C20—C21	120.0 (3)
O2—Ni1—O4	91.55 (9)	C19—C20—H20A	120.0
N3—Ni1—O4	159.34 (9)	C21—C20—H20A	120.0
N4—Ni1—O4	94.17 (9)	C22—C21—C20	121.0 (3)
O5—Ni1—O1	94.26 (9)	C22—C21—H21A	119.5
O2—Ni1—O1	61.40 (8)	C20—C21—H21A	119.5
N3—Ni1—O1	91.46 (9)	C21—C22—C23	119.3 (3)
N4—Ni1—O1	159.99 (9)	C21—C22—H22A	120.3
O4—Ni1—O1	84.95 (9)	C23—C22—H22A	120.3
N1—O1—Ni1	89.87 (18)	C22—C23—C24	119.9 (3)
N1—O2—Ni1	92.94 (17)	C22—C23—H23A	120.0
N2—O4—Ni1	90.24 (17)	C24—C23—H23A	120.0
N2—O5—Ni1	93.21 (17)	C19—C24—C23	120.9 (3)
N3—C1—N5	116.2 (2)	C19—C24—H24A	119.5
N3—C1—C2	120.3 (2)	C23—C24—H24A	119.5
N5—C1—C2	123.5 (3)	C26—C25—C30	118.5 (3)
C3—C2—C1	119.7 (3)	C26—C25—C11	122.4 (3)
C3—C2—H2A	120.1	C30—C25—C11	119.1 (3)
C1—C2—H2A	120.1	C25—C26—C27	120.7 (3)
C2—C3—C4	120.2 (3)	C25—C26—H26A	119.7
C2—C3—H3A	119.9	C27—C26—H26A	119.7
C4—C3—H3A	119.9	C28—C27—C26	120.3 (4)
C5—C4—C3	117.6 (3)	C28—C27—H27A	119.9
C5—C4—H4A	121.2	C26—C27—H27A	119.9
C3—C4—H4A	121.2	C27—C28—C29	120.3 (4)
C4—C5—N3	124.3 (3)	C27—C28—H28A	119.9
C4—C5—H5A	117.9	C29—C28—H28A	119.9
N3—C5—H5A	117.9	C28—C29—C30	119.7 (4)
N6—C6—N4	116.0 (2)	C28—C29—H29A	120.2
N6—C6—C7	123.4 (2)	C30—C29—H29A	120.2
N4—C6—C7	120.6 (3)	C29—C30—C25	120.5 (3)
C8—C7—C6	119.8 (3)	C29—C30—H30A	119.7
C8—C7—H7A	120.1	C25—C30—H30A	119.7
C6—C7—H7A	120.1	C32—C31—C36	117.6 (3)
C7—C8—C9	119.9 (3)	C32—C31—C12	124.0 (3)
C7—C8—H8A	120.1	C36—C31—C12	118.3 (2)
C9—C8—H8A	120.1	C31—C32—C33	120.4 (3)
C10—C9—C8	117.9 (3)	C31—C32—H32A	119.8
C10—C9—H9A	121.0	C33—C32—H32A	119.8
C8—C9—H9A	121.0	C34—C33—C32	120.8 (3)
N4—C10—C9	124.3 (3)	C34—C33—H33A	119.6
N4—C10—H10A	117.8	C32—C33—H33A	119.6
C9—C10—H10A	117.8	C35—C34—C33	119.5 (3)
N5—C11—C13	111.5 (2)	C35—C34—H34A	120.3
N5—C11—C19	109.0 (2)	C33—C34—H34A	120.3
C13—C11—C19	114.1 (2)	C34—C35—C36	119.9 (3)
N5—C11—C25	106.0 (2)	C34—C35—H35A	120.0
C13—C11—C25	107.0 (2)	C36—C35—H35A	120.0
C19—C11—C25	108.9 (2)	C35—C36—C31	121.7 (3)
N6—C12—C43	112.1 (2)	C35—C36—H36A	119.1
N6—C12—C31	108.5 (2)	C31—C36—H36A	119.1
C43—C12—C31	113.4 (2)	C38—C37—C42	117.9 (3)
N6—C12—C37	104.1 (2)	C38—C37—C12	123.8 (3)
C43—C12—C37	107.5 (2)	C42—C37—C12	118.3 (3)
C31—C12—C37	110.8 (2)	C39—C38—C37	120.6 (3)
C18—C13—C14	117.8 (3)	C39—C38—H38A	119.7
C18—C13—C11	122.8 (3)	C37—C38—H38A	119.7
C14—C13—C11	119.4 (3)	C40—C39—C38	120.7 (3)
C15—C14—C13	120.9 (3)	C40—C39—H39A	119.7
C15—C14—H14A	119.6	C38—C39—H39A	119.7
C13—C14—H14A	119.6	C41—C40—C39	119.6 (3)
C16—C15—C14	120.2 (4)	C41—C40—H40A	120.2
C16—C15—H15A	119.9	C39—C40—H40A	120.2
C14—C15—H15A	119.9	C40—C41—C42	120.2 (3)
C15—C16—C17	120.2 (4)	C40—C41—H41A	119.9
C15—C16—H16A	119.9	C42—C41—H41A	119.9
C17—C16—H16A	119.9	C41—C42—C37	120.8 (3)
C16—C17—C18	120.4 (4)	C41—C42—H42A	119.6
C16—C17—H17A	119.8	C37—C42—H42A	119.6
C18—C17—H17A	119.8	C48—C43—C44	117.1 (3)
C13—C18—C17	120.6 (3)	C48—C43—C12	123.5 (2)
C13—C18—H18A	119.7	C44—C43—C12	119.3 (2)
C17—C18—H18A	119.7	C45—C44—C43	120.9 (3)
C20—C19—C24	118.7 (3)	C45—C44—H44A	119.5
C20—C19—C11	123.5 (3)	C43—C44—H44A	119.5
C24—C19—C11	117.7 (2)	C46—C45—C44	121.0 (3)
O3—N1—O1	123.5 (3)	C46—C45—H45A	119.5
O3—N1—O2	121.0 (3)	C44—C45—H45A	119.5
O1—N1—O2	115.5 (2)	C45—C46—C47	118.9 (3)
O6—N2—O4	124.3 (3)	C45—C46—H46A	120.5
O6—N2—O5	121.0 (3)	C47—C46—H46A	120.5
O4—N2—O5	114.7 (3)	C46—C47—C48	120.5 (3)
C1—N3—C5	117.8 (2)	C46—C47—H47A	119.8
C1—N3—Ni1	126.62 (18)	C48—C47—H47A	119.8
C5—N3—Ni1	115.33 (19)	C43—C48—C47	121.4 (3)
C10—N4—C6	117.4 (2)	C43—C48—H48A	119.3
C10—N4—Ni1	114.90 (18)	C47—C48—H48A	119.3
C6—N4—Ni1	127.43 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O2	0.86	2.16	2.994 (3)	165
N6—H6A···O5	0.86	2.22	3.048 (3)	162

Experimental details

Crystal data
Chemical formula	[Ni(NO₃)₂(C₂₄H₂₀N₂)₂]
M_r	855.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.287 (2), 23.462 (5), 17.868 (4)
β (°)	105.266 (3)
V (Å³)	4160.3 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.53 × 0.52 × 0.47

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.733, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	20535, 7279, 4928
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.01
No. of reflections	7279
No. of parameters	550
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008.

Selected bond lengths (Å) top

Ni1—O5	2.050 (2)	Ni1—N4	2.062 (2)
Ni1—O2	2.0607 (19)	Ni1—O4	2.133 (2)
Ni1—N3	2.061 (2)	Ni1—O1	2.150 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O2	0.86	2.16	2.994 (3)	164.8
N6—H6A···O5	0.86	2.22	3.048 (3)	161.6

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fang, Y., Huang, C.-Y., Zhu, Z.-M., Yu, X.-L. & You, W.-S. (2006). Acta Cryst. E62, m3347–m3348. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). 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
Zhang, G.-N. (2008). Acta Cryst. E64, m357. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, G.-N., Fang, Y., Huang, C.-Y. & You, W.-S. (2007). Acta Cryst. E63, m2247. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 12| December 2010| Page m1521

https://doi.org/10.1107/S1600536810044624

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