{3-Methyl-2-[(1-oxido-2-naphth­yl)methyl­idene­amino-κ2O,N]butano­ato-κO}(1H-pyrazole-κN2)nickel(II)

Peng, Q.-L.; Zhao, G.-Q.; Chen, L.-H.; Xue, L.-W.

doi:10.1107/S1600536810032472

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1127-m1128

https://doi.org/10.1107/S1600536810032472

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{3-Methyl-2-[(1-oxido-2-naphthyl)methylideneamino-κ²O,N]butanoato-κO}(1H-pyrazole-κN²)nickel(II)

Qin-Long Peng,^a ^* Gan-Qing Zhao,^a Li-Hua Chen ^a and Ling-Wei Xue ^a

^aSchool of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
^*Correspondence e-mail: jecky_2002@163.com

(Received 11 July 2010; accepted 12 August 2010; online 18 August 2010)

In either of the two independent molecules within the asymmetric unit of the title compound, [Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)], the Ni^II atom is coordinated by the two N atoms and two O atoms in a distorted square-planar geometry. The crystal packing is stabilized by strong and weak intermolecular C—H⋯O hydrogen bonds, as well as weak centroid–centroid π-stacking interactions [centroid–centroid separation = 3.526 (3) Å].

Related literature

For complexes of Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, see: Li et al. (2010 ); Vergopoulos et al. (1993 ); Usman et al. (2003 ). For related structures, see: Basu Baul et al. (2007 ); Ebel & Rehder (2003 ); Maniukiewicz & Bukowska-Strzyżewska (2001 ); Xue et al. (2009 ); Qiu et al. (2008 ). For the synthesis, see: Plesch et al. (1997 ).

Experimental

Crystal data

[Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)]
M_r = 396.08
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.5089 (11) Å
b = 16.6194 (16) Å
c = 18.9934 (19) Å
V = 3632.9 (6) Å³
Z = 8
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.735, T_max = 0.772
18967 measured reflections
6400 independent reflections
4910 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.108
S = 1.02
6400 reflections
473 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 2792 Friedel pairs
Flack parameter: −0.015 (16)

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.805 (3)
Ni1—N1	1.833 (3)
Ni1—O2	1.852 (3)
Ni1—N2	1.900 (3)

O1—Ni1—N1	94.55 (15)
O1—Ni1—O2	176.92 (16)
N1—Ni1—O2	86.20 (15)
O1—Ni1—N2	89.98 (16)
N1—Ni1—N2	173.95 (16)
O2—Ni1—N2	89.49 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2ⁱ	0.93	2.59	3.476 (6)	159
C14—H14⋯O6ⁱⁱ	0.98	2.42	3.318 (6)	153
C18—H18⋯O6ⁱⁱⁱ	0.93	1.87	2.798 (5)	178
C37—H37⋯O3^iv	0.93	1.85	2.756 (5)	163
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Table 3
Weak Cg–Cg intermolecular interactions of (I) (Å)

Distance	Cg1–Cg10	Cg3–Cg9	Cg4–Cg7	Cg4–Cg9
Centroid–centroid distance	3.940 (3)	3.709 (2)	3.526 (3)	3.932 (3)
Notes: CgI–CgJ = centroid–centroid distance between planes I and J (Å); Cg1: Ni1/O2/C13/C12/N1; Cg3: Ni1/O1/C1/C10/C11/N1; Cg4: C1/C2/C3/C4/C9/C10; Cg7: Ni2/O5/C32/C31/N4; Cg9: Ni2/O4/C20/C29/C30/N4; Cg10: C20/C21/C22/C23/C28/C29.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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 global, I. DOI: https://doi.org/10.1107/S1600536810032472/jj2044sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032472/jj2044Isup2.hkl

checkCIF report

Comment top

Complexes of Shiff base ligands composed of salicylaldehyde, 2-formylpyidine or their analogues, and α-amino acid always have attracted attention due to the important biomolecules–α-amino acid and manifold structure (Vergopoulos et al., 1993; Usman et al., 2003; Li et al., 2010). Several structural studies have been performed on Shiff base transition metal complex derived from 1-hydroxy-2-naphthaldehyde and α-amino acid (Ebel et al., 2003; Qiu et al., 2008; Xue et al., 2009). We report here the crystal structure of the title Ni^IIcomplex, (I), [Ni(C₁₆H₁₅N₁O₃)(C₃H₄N₂)].

In the title complex, the Ni^IIatom is in a distorted square-planar coordination geometry (Fig. 1; table 1). Three basal positions are occupied by three donor atoms from the tridentate Schiff base ligand, which furnishes an O–N–O donor set, with the fourth position occupied by one N atom from the pyrazole ligand.

The dihedral angle between the mean planes of the naphthalene and pyrazole rings is 16.(7)°. Strong and weak intermolecular C—H···O hydrogen bonds (Fig. 2; Table 2) and weak Cg···Cg π-stacking interactions [shortest centroid-centroid separation = 3.526 (3) Å] contribute to crystal packing (Table 3).

Related literature top

For complexes of Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, see: Li et al. (2010); Vergopoulos et al. (1993); Usman et al. (2003). For related structures, see: Basu Baul et al. (2007); Ebel & Rehder (2003); Maniukiewicz & Bukowska-Strzyżewska (2001); Xue et al. (2009); Qiu et al. (2008). For the synthesis, see Plesch et al. (1997).

Experimental top

The title compound was synthesized as described in the literature (Plesch et al., 1997). To L-valine (1.00 mmol) and potassium hydroxide (1.00 mmol) in 10 ml of methanol and 5 ml of water was added 2-Hydroxy-1-naphthaldehyde (1.00 mmol in 10 ml of methanol) dropwise.The yellow solution was stirred for 2.0 h at 333 K. The resultant mixture was added dropwise to Ni (II) nitrate Hexahydrate (1.00 mmol) and pyrazole (1.00 mmol) in an aqueous methanolic solution (20 ml, 1:1 v/v), and heated with stirring for 4.0 h at 333 K. The brown solution was filtered and left for several days, brown crystals had formed that were filtered off, washed with water, and dried under vacuum.

Structure description top

For complexes of Schiff base ligands composed of salicylaldehyde, 2-formylpyridine or their analogues, see: Li et al. (2010); Vergopoulos et al. (1993); Usman et al. (2003). For related structures, see: Basu Baul et al. (2007); Ebel & Rehder (2003); Maniukiewicz & Bukowska-Strzyżewska (2001); Xue et al. (2009); Qiu et al. (2008). For the synthesis, see Plesch et al. (1997).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 structure of the title compound, (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the crystal packing. Hydrogen bonds are shown as red dashed lines.

{3-Methyl-2-[(1-oxido-2-naphthyl)methylideneamino- κ²O,N]butanoato-κO}(1H-pyrazole- κN²)nickel(II) top

Crystal data top

[Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)]	F(000) = 1648
M_r = 396.08	D_x = 1.448 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4302 reflections
a = 11.5089 (11) Å	θ = 2.4–21.1°
b = 16.6194 (16) Å	µ = 1.09 mm⁻¹
c = 18.9934 (19) Å	T = 296 K
V = 3632.9 (6) Å³	Block, brown
Z = 8	0.30 × 0.30 × 0.25 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6400 independent reflections
Radiation source: fine-focus sealed tube	4910 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→13
T_min = 0.735, T_max = 0.772	k = −19→19
18967 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0469P)² + 0.9539P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
6400 reflections	Δρ_max = 0.53 e Å⁻³
473 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2792 Friedel pairs [PLEASE CHECK]
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.015 (16)

Crystal data top

[Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)]	V = 3632.9 (6) Å³
M_r = 396.08	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.5089 (11) Å	µ = 1.09 mm⁻¹
b = 16.6194 (16) Å	T = 296 K
c = 18.9934 (19) Å	0.30 × 0.30 × 0.25 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6400 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4910 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.772	R_int = 0.045
18967 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.108	Δρ_max = 0.53 e Å⁻³
S = 1.02	Δρ_min = −0.36 e Å⁻³
6400 reflections	Absolute structure: Flack (1983), 2792 Friedel pairs [PLEASE CHECK]
473 parameters	Absolute structure parameter: −0.015 (16)
0 restraints

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	0.75779 (5)	0.07571 (3)	0.05529 (3)	0.04451 (17)
Ni2	0.29080 (5)	0.80826 (3)	0.31116 (3)	0.04473 (17)
C1	0.5662 (4)	0.1225 (3)	0.1366 (3)	0.0445 (12)
C2	0.4616 (4)	0.1673 (3)	0.1395 (3)	0.0560 (13)
H2	0.4354	0.1933	0.0992	0.067*
C3	0.3991 (5)	0.1734 (3)	0.1993 (3)	0.0598 (14)
H3	0.3285	0.2005	0.1986	0.072*
C4	0.4389 (5)	0.1392 (3)	0.2630 (3)	0.0532 (14)
C5	0.3769 (5)	0.1514 (3)	0.3268 (3)	0.0623 (15)
H5	0.3064	0.1787	0.3260	0.075*
C6	0.4201 (6)	0.1231 (3)	0.3901 (3)	0.0672 (16)
H6	0.3792	0.1317	0.4316	0.081*
C7	0.5240 (5)	0.0821 (3)	0.3912 (3)	0.0588 (14)
H7	0.5536	0.0633	0.4337	0.071*
C8	0.5844 (5)	0.0688 (3)	0.3298 (2)	0.0531 (13)
H8	0.6537	0.0401	0.3318	0.064*
C9	0.5449 (4)	0.0969 (3)	0.2639 (3)	0.0432 (12)
C10	0.6076 (4)	0.0857 (3)	0.1986 (2)	0.0402 (10)
C11	0.7082 (4)	0.0369 (2)	0.1959 (2)	0.0435 (11)
H11	0.7295	0.0102	0.2369	0.052*
C12	0.8739 (4)	−0.0294 (3)	0.1441 (2)	0.0464 (12)
H12	0.9156	−0.0200	0.1883	0.056*
C13	0.9522 (5)	−0.0079 (3)	0.0842 (3)	0.0482 (12)
C14	0.8356 (5)	−0.1181 (3)	0.1417 (3)	0.0567 (14)
H14	0.7791	−0.1253	0.1798	0.068*
C15	0.7731 (6)	−0.1393 (3)	0.0738 (3)	0.0812 (18)
H15A	0.8284	−0.1428	0.0361	0.122*
H15B	0.7170	−0.0983	0.0632	0.122*
H15C	0.7344	−0.1900	0.0791	0.122*
C16	0.9363 (6)	−0.1746 (4)	0.1576 (4)	0.092 (2)
H16A	0.9917	−0.1723	0.1199	0.139*
H16B	0.9077	−0.2286	0.1622	0.139*
H16C	0.9731	−0.1585	0.2007	0.139*
N3	0.6506 (5)	0.1453 (3)	−0.0732 (3)	0.0952 (18)
H3A	0.5839	0.1544	−0.0544	0.114*
C18	0.7893 (4)	0.1369 (2)	−0.1493 (2)	0.0391 (10)
H18	0.8320	0.1392	−0.1909	0.047*
C19	0.8288 (5)	0.1139 (3)	−0.0877 (3)	0.0563 (14)
H19	0.9049	0.0974	−0.0799	0.068*
C20	0.1022 (4)	0.7048 (3)	0.2868 (3)	0.0452 (12)
C21	0.0003 (5)	0.6677 (3)	0.3148 (3)	0.0568 (13)
H21	−0.0242	0.6806	0.3601	0.068*
C22	−0.0608 (5)	0.6140 (3)	0.2766 (3)	0.0648 (16)
H22	−0.1264	0.5905	0.2964	0.078*
C23	−0.0286 (5)	0.5921 (3)	0.2073 (3)	0.0541 (14)
C24	−0.0923 (5)	0.5350 (3)	0.1676 (4)	0.0743 (18)
H24	−0.1584	0.5120	0.1874	0.089*
C25	−0.0604 (6)	0.5130 (4)	0.1024 (4)	0.086 (2)
H25	−0.1032	0.4748	0.0777	0.103*
C26	0.0366 (6)	0.5477 (4)	0.0724 (4)	0.0798 (19)
H26	0.0583	0.5334	0.0269	0.096*
C27	0.1015 (5)	0.6029 (3)	0.1087 (3)	0.0609 (15)
H27	0.1663	0.6253	0.0871	0.073*
C28	0.0734 (4)	0.6266 (3)	0.1773 (3)	0.0484 (12)
C29	0.1375 (4)	0.6856 (3)	0.2179 (2)	0.0426 (11)
C30	0.2362 (4)	0.7240 (2)	0.1880 (2)	0.0407 (10)
H30	0.2559	0.7099	0.1422	0.049*
C31	0.4015 (4)	0.8117 (3)	0.1815 (2)	0.0440 (11)
H31	0.4416	0.7687	0.1558	0.053*
C32	0.4824 (5)	0.8441 (3)	0.2381 (2)	0.0444 (11)
C33	0.3714 (5)	0.8798 (3)	0.1293 (3)	0.0627 (16)
H33	0.4463	0.9012	0.1134	0.075*
C34	0.3129 (8)	0.8482 (5)	0.0640 (3)	0.119 (3)
H34A	0.2402	0.8238	0.0766	0.179*
H34B	0.3620	0.8089	0.0420	0.179*
H34C	0.2993	0.8918	0.0319	0.179*
C35	0.3109 (6)	0.9496 (3)	0.1654 (3)	0.086 (2)
H35A	0.2957	0.9913	0.1317	0.130*
H35B	0.3597	0.9703	0.2022	0.130*
H35C	0.2388	0.9313	0.1853	0.130*
N6	0.2387 (6)	0.8183 (3)	0.4640 (3)	0.1060 (19)
H6A	0.1960	0.7759	0.4666	0.127*
C37	0.3311 (4)	0.9271 (3)	0.4934 (2)	0.0412 (11)
H37	0.3609	0.9704	0.5186	0.049*
C38	0.3433 (4)	0.9138 (3)	0.4260 (3)	0.0578 (14)
H38	0.3861	0.9471	0.3964	0.069*
N1	0.7731 (3)	0.0262 (2)	0.14102 (18)	0.0418 (9)
N2	0.7483 (4)	0.1169 (2)	−0.03787 (18)	0.0473 (9)
C17	0.6775 (6)	0.1564 (3)	−0.1422 (3)	0.0676 (17)
H17	0.6277	0.1741	−0.1775	0.081*
N4	0.3010 (3)	0.7767 (2)	0.21896 (18)	0.0425 (9)
N5	0.2891 (4)	0.8490 (2)	0.40427 (19)	0.0480 (10)
C36	0.2692 (7)	0.8680 (4)	0.5186 (3)	0.086 (2)
H36	0.2492	0.8608	0.5656	0.103*
O1	0.6178 (3)	0.1191 (2)	0.07517 (16)	0.0529 (9)
O2	0.9049 (3)	0.03658 (19)	0.03564 (16)	0.0501 (8)
O3	1.0518 (3)	−0.0330 (2)	0.07990 (19)	0.0621 (10)
O4	0.1546 (3)	0.7567 (2)	0.32823 (16)	0.0541 (9)
O5	0.4362 (3)	0.8548 (2)	0.29918 (17)	0.0534 (9)
O6	0.5840 (3)	0.8613 (2)	0.22488 (17)	0.0587 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0446 (4)	0.0483 (3)	0.0407 (3)	0.0047 (3)	0.0006 (3)	0.0060 (3)
Ni2	0.0416 (4)	0.0469 (3)	0.0456 (3)	−0.0031 (3)	0.0020 (3)	−0.0033 (3)
C1	0.042 (3)	0.041 (3)	0.050 (3)	0.001 (2)	0.003 (2)	−0.002 (2)
C2	0.047 (3)	0.059 (3)	0.062 (3)	0.008 (3)	−0.003 (3)	0.004 (3)
C3	0.046 (3)	0.053 (3)	0.081 (4)	0.012 (3)	0.006 (3)	0.001 (3)
C4	0.057 (4)	0.041 (3)	0.061 (3)	−0.003 (3)	0.012 (3)	−0.004 (3)
C5	0.054 (3)	0.054 (3)	0.079 (4)	0.002 (3)	0.022 (3)	−0.013 (3)
C6	0.085 (5)	0.058 (3)	0.059 (4)	−0.008 (3)	0.020 (3)	−0.005 (3)
C7	0.070 (4)	0.059 (3)	0.048 (3)	−0.006 (3)	0.011 (3)	0.000 (3)
C8	0.058 (3)	0.051 (3)	0.051 (3)	−0.003 (3)	0.004 (3)	0.001 (2)
C9	0.046 (3)	0.033 (2)	0.050 (3)	−0.004 (2)	0.005 (2)	−0.002 (2)
C10	0.033 (2)	0.039 (2)	0.048 (3)	0.001 (2)	0.000 (2)	0.003 (2)
C11	0.047 (3)	0.046 (2)	0.038 (2)	−0.007 (2)	−0.004 (2)	0.001 (2)
C12	0.038 (3)	0.055 (3)	0.047 (3)	0.003 (2)	0.004 (2)	0.008 (2)
C13	0.045 (3)	0.048 (3)	0.051 (3)	0.001 (3)	−0.005 (2)	0.008 (2)
C14	0.045 (3)	0.051 (3)	0.074 (4)	0.005 (3)	0.018 (3)	0.013 (3)
C15	0.084 (5)	0.066 (3)	0.094 (4)	−0.007 (4)	0.009 (4)	−0.008 (3)
C16	0.073 (4)	0.072 (4)	0.132 (6)	0.027 (4)	0.030 (4)	0.038 (4)
N3	0.086 (4)	0.104 (4)	0.096 (4)	0.024 (3)	−0.001 (3)	0.011 (3)
C18	0.043 (3)	0.045 (2)	0.030 (2)	0.007 (2)	0.004 (2)	0.0113 (18)
C19	0.046 (3)	0.054 (3)	0.069 (4)	0.004 (3)	0.005 (3)	0.009 (3)
C20	0.041 (3)	0.041 (3)	0.054 (3)	0.003 (2)	−0.001 (2)	0.001 (2)
C21	0.050 (3)	0.063 (3)	0.057 (3)	−0.002 (3)	0.011 (3)	0.005 (3)
C22	0.047 (3)	0.057 (3)	0.091 (5)	−0.008 (3)	0.006 (3)	0.001 (3)
C23	0.045 (3)	0.044 (3)	0.073 (4)	0.002 (2)	−0.003 (3)	−0.001 (3)
C24	0.054 (4)	0.065 (4)	0.104 (5)	−0.018 (3)	0.007 (4)	−0.012 (4)
C25	0.068 (5)	0.081 (4)	0.108 (6)	−0.025 (4)	−0.003 (4)	−0.033 (4)
C26	0.072 (4)	0.084 (4)	0.084 (5)	−0.015 (4)	0.000 (4)	−0.028 (4)
C27	0.048 (3)	0.065 (3)	0.070 (4)	−0.011 (3)	−0.003 (3)	−0.014 (3)
C28	0.041 (3)	0.043 (3)	0.061 (3)	0.000 (2)	−0.005 (2)	−0.002 (2)
C29	0.035 (3)	0.037 (2)	0.057 (3)	0.003 (2)	−0.002 (2)	0.003 (2)
C30	0.042 (3)	0.035 (2)	0.045 (2)	0.005 (2)	−0.006 (2)	−0.0049 (19)
C31	0.043 (3)	0.047 (2)	0.043 (3)	−0.001 (2)	0.007 (2)	0.000 (2)
C32	0.043 (3)	0.043 (3)	0.047 (3)	−0.003 (2)	−0.001 (2)	0.006 (2)
C33	0.072 (4)	0.065 (4)	0.051 (3)	−0.013 (3)	−0.018 (3)	0.007 (3)
C34	0.147 (7)	0.124 (6)	0.086 (5)	0.000 (6)	−0.034 (5)	0.026 (4)
C35	0.096 (5)	0.057 (3)	0.106 (5)	0.001 (4)	−0.033 (4)	0.017 (3)
N6	0.127 (5)	0.101 (4)	0.090 (4)	−0.023 (4)	0.026 (4)	0.006 (3)
C37	0.035 (3)	0.049 (3)	0.040 (3)	−0.013 (2)	0.003 (2)	−0.014 (2)
C38	0.043 (3)	0.060 (3)	0.071 (4)	−0.006 (3)	0.004 (3)	−0.006 (3)
N1	0.039 (2)	0.042 (2)	0.045 (2)	0.0053 (19)	0.0007 (19)	0.0027 (16)
N2	0.041 (2)	0.053 (2)	0.048 (2)	0.008 (2)	0.000 (2)	0.0066 (17)
C17	0.089 (5)	0.078 (4)	0.035 (3)	0.002 (4)	−0.001 (3)	0.021 (3)
N4	0.037 (2)	0.0382 (19)	0.052 (2)	0.0037 (19)	0.0017 (19)	0.0009 (17)
N5	0.048 (3)	0.046 (2)	0.050 (2)	−0.007 (2)	0.009 (2)	−0.0032 (18)
C36	0.111 (6)	0.106 (5)	0.041 (3)	0.004 (5)	−0.008 (4)	−0.021 (3)
O1	0.051 (2)	0.064 (2)	0.0435 (19)	0.0131 (18)	0.0023 (16)	0.0064 (16)
O2	0.042 (2)	0.059 (2)	0.050 (2)	0.0077 (17)	0.0079 (16)	0.0131 (16)
O3	0.038 (2)	0.077 (2)	0.072 (3)	0.009 (2)	0.0085 (17)	0.026 (2)
O4	0.053 (2)	0.057 (2)	0.053 (2)	−0.0091 (18)	0.0068 (17)	−0.0074 (17)
O5	0.042 (2)	0.071 (2)	0.047 (2)	−0.0090 (18)	−0.0001 (16)	−0.0069 (17)
O6	0.040 (2)	0.082 (2)	0.055 (2)	−0.0127 (19)	0.0029 (17)	0.0037 (18)

Geometric parameters (Å, º) top

Ni1—O1	1.805 (3)	C18—H18	0.9300
Ni1—N1	1.833 (3)	C19—N2	1.325 (6)
Ni1—O2	1.852 (3)	C19—H19	0.9300
Ni1—N2	1.900 (3)	C20—O4	1.313 (5)
Ni2—O4	1.816 (3)	C20—C29	1.406 (6)
Ni2—N4	1.832 (4)	C20—C21	1.428 (7)
Ni2—O5	1.857 (3)	C21—C22	1.349 (7)
Ni2—N5	1.894 (4)	C21—H21	0.9300
C1—O1	1.311 (5)	C22—C23	1.415 (7)
C1—C10	1.410 (6)	C22—H22	0.9300
C1—C2	1.417 (7)	C23—C24	1.417 (7)
C2—C3	1.347 (7)	C23—C28	1.425 (7)
C2—H2	0.9300	C24—C25	1.343 (8)
C3—C4	1.413 (7)	C24—H24	0.9300
C3—H3	0.9300	C25—C26	1.380 (8)
C4—C9	1.408 (7)	C25—H25	0.9300
C4—C5	1.420 (7)	C26—C27	1.368 (7)
C5—C6	1.384 (8)	C26—H26	0.9300
C5—H5	0.9300	C27—C28	1.400 (7)
C6—C7	1.377 (8)	C27—H27	0.9300
C6—H6	0.9300	C28—C29	1.449 (6)
C7—C8	1.374 (7)	C29—C30	1.421 (6)
C7—H7	0.9300	C30—N4	1.292 (5)
C8—C9	1.412 (7)	C30—H30	0.9300
C8—H8	0.9300	C31—N4	1.477 (6)
C9—C10	1.446 (6)	C31—C32	1.522 (7)
C10—C11	1.415 (6)	C31—C33	1.543 (7)
C11—N1	1.294 (5)	C31—H31	0.9800
C11—H11	0.9300	C32—O6	1.230 (6)
C12—N1	1.484 (6)	C32—O5	1.288 (5)
C12—C13	1.496 (7)	C33—C34	1.505 (8)
C12—C14	1.540 (7)	C33—C35	1.517 (8)
C12—H12	0.9800	C33—H33	0.9800
C13—O3	1.222 (6)	C34—H34A	0.9600
C13—O2	1.300 (5)	C34—H34B	0.9600
C14—C15	1.519 (7)	C34—H34C	0.9600
C14—C16	1.521 (7)	C35—H35A	0.9600
C14—H14	0.9800	C35—H35B	0.9600
C15—H15A	0.9600	C35—H35C	0.9600
C15—H15B	0.9600	N6—C36	1.372 (7)
C15—H15C	0.9600	N6—N5	1.372 (6)
C16—H16A	0.9600	N6—H6A	0.8600
C16—H16B	0.9600	C37—C36	1.304 (8)
C16—H16C	0.9600	C37—C38	1.307 (6)
N3—C17	1.359 (7)	C37—H37	0.9300
N3—N2	1.393 (6)	C38—N5	1.312 (6)
N3—H3A	0.8600	C38—H38	0.9300
C18—C19	1.312 (6)	C17—H17	0.9300
C18—C17	1.334 (7)	C36—H36	0.9300

O1—Ni1—N1	94.55 (15)	C20—C21—H21	119.6
O1—Ni1—O2	176.92 (16)	C21—C22—C23	122.3 (5)
N1—Ni1—O2	86.20 (15)	C21—C22—H22	118.8
O1—Ni1—N2	89.98 (16)	C23—C22—H22	118.8
N1—Ni1—N2	173.95 (16)	C22—C23—C24	122.0 (5)
O2—Ni1—N2	89.49 (16)	C22—C23—C28	118.9 (5)
O4—Ni2—N4	95.23 (16)	C24—C23—C28	119.0 (5)
O4—Ni2—O5	174.97 (15)	C25—C24—C23	122.1 (6)
N4—Ni2—O5	86.79 (16)	C25—C24—H24	119.0
O4—Ni2—N5	89.59 (16)	C23—C24—H24	119.0
N4—Ni2—N5	174.72 (17)	C24—C25—C26	119.2 (6)
O5—Ni2—N5	88.58 (16)	C24—C25—H25	120.4
O1—C1—C10	124.9 (4)	C26—C25—H25	120.4
O1—C1—C2	116.3 (4)	C27—C26—C25	120.9 (6)
C10—C1—C2	118.8 (4)	C27—C26—H26	119.5
C3—C2—C1	121.7 (5)	C25—C26—H26	119.5
C3—C2—H2	119.1	C26—C27—C28	122.2 (5)
C1—C2—H2	119.1	C26—C27—H27	118.9
C2—C3—C4	121.2 (5)	C28—C27—H27	118.9
C2—C3—H3	119.4	C27—C28—C23	116.6 (5)
C4—C3—H3	119.4	C27—C28—C29	124.7 (5)
C9—C4—C3	119.5 (5)	C23—C28—C29	118.6 (5)
C9—C4—C5	119.7 (5)	C20—C29—C30	120.1 (4)
C3—C4—C5	120.7 (5)	C20—C29—C28	120.1 (4)
C6—C5—C4	120.8 (5)	C30—C29—C28	119.8 (4)
C6—C5—H5	119.6	N4—C30—C29	125.7 (4)
C4—C5—H5	119.6	N4—C30—H30	117.1
C7—C6—C5	119.6 (5)	C29—C30—H30	117.1
C7—C6—H6	120.2	N4—C31—C32	106.1 (4)
C5—C6—H6	120.2	N4—C31—C33	115.0 (4)
C8—C7—C6	120.4 (5)	C32—C31—C33	109.4 (4)
C8—C7—H7	119.8	N4—C31—H31	108.7
C6—C7—H7	119.8	C32—C31—H31	108.7
C7—C8—C9	122.4 (5)	C33—C31—H31	108.7
C7—C8—H8	118.8	O6—C32—O5	123.0 (4)
C9—C8—H8	118.8	O6—C32—C31	121.3 (4)
C4—C9—C8	117.1 (5)	O5—C32—C31	115.7 (4)
C4—C9—C10	119.1 (4)	C34—C33—C35	115.7 (6)
C8—C9—C10	123.8 (4)	C34—C33—C31	111.9 (5)
C1—C10—C11	119.6 (4)	C35—C33—C31	111.9 (4)
C1—C10—C9	119.4 (4)	C34—C33—H33	105.5
C11—C10—C9	120.9 (4)	C35—C33—H33	105.5
N1—C11—C10	125.5 (4)	C31—C33—H33	105.5
N1—C11—H11	117.3	C33—C34—H34A	109.5
C10—C11—H11	117.3	C33—C34—H34B	109.5
N1—C12—C13	107.0 (4)	H34A—C34—H34B	109.5
N1—C12—C14	111.9 (4)	C33—C34—H34C	109.5
C13—C12—C14	112.3 (4)	H34A—C34—H34C	109.5
N1—C12—H12	108.5	H34B—C34—H34C	109.5
C13—C12—H12	108.5	C33—C35—H35A	109.5
C14—C12—H12	108.5	C33—C35—H35B	109.5
O3—C13—O2	122.7 (5)	H35A—C35—H35B	109.5
O3—C13—C12	122.3 (4)	C33—C35—H35C	109.5
O2—C13—C12	115.0 (4)	H35A—C35—H35C	109.5
C15—C14—C16	112.8 (5)	H35B—C35—H35C	109.5
C15—C14—C12	112.4 (4)	C36—N6—N5	107.1 (5)
C16—C14—C12	111.5 (5)	C36—N6—H6A	126.5
C15—C14—H14	106.5	N5—N6—H6A	126.5
C16—C14—H14	106.5	C36—C37—C38	106.9 (5)
C12—C14—H14	106.5	C36—C37—H37	126.5
C14—C15—H15A	109.5	C38—C37—H37	126.5
C14—C15—H15B	109.5	C37—C38—N5	113.3 (5)
H15A—C15—H15B	109.5	C37—C38—H38	123.3
C14—C15—H15C	109.5	N5—C38—H38	123.3
H15A—C15—H15C	109.5	C11—N1—C12	120.3 (4)
H15B—C15—H15C	109.5	C11—N1—Ni1	126.8 (3)
C14—C16—H16A	109.5	C12—N1—Ni1	112.9 (3)
C14—C16—H16B	109.5	C19—N2—N3	103.4 (4)
H16A—C16—H16B	109.5	C19—N2—Ni1	127.7 (3)
C14—C16—H16C	109.5	N3—N2—Ni1	128.1 (4)
H16A—C16—H16C	109.5	C18—C17—N3	106.5 (5)
H16B—C16—H16C	109.5	C18—C17—H17	126.7
C17—N3—N2	109.1 (5)	N3—C17—H17	126.7
C17—N3—H3A	125.4	C30—N4—C31	120.0 (4)
N2—N3—H3A	125.4	C30—N4—Ni2	126.3 (3)
C19—C18—C17	108.3 (5)	C31—N4—Ni2	113.5 (3)
C19—C18—H18	125.8	C38—N5—N6	104.2 (4)
C17—C18—H18	125.8	C38—N5—Ni2	125.6 (4)
C18—C19—N2	112.6 (5)	N6—N5—Ni2	130.0 (3)
C18—C19—H19	123.7	C37—C36—N6	108.4 (5)
N2—C19—H19	123.7	C37—C36—H36	125.8
O4—C20—C29	125.0 (4)	N6—C36—H36	125.8
O4—C20—C21	115.9 (4)	C1—O1—Ni1	127.4 (3)
C29—C20—C21	119.1 (4)	C13—O2—Ni1	116.1 (3)
C22—C21—C20	120.9 (5)	C20—O4—Ni2	126.8 (3)
C22—C21—H21	119.6	C32—O5—Ni2	115.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.93	2.59	3.476 (6)	159
C14—H14···O6ⁱⁱ	0.98	2.42	3.318 (6)	153
C18—H18···O6ⁱⁱⁱ	0.93	1.87	2.798 (5)	178
C37—H37···O3^iv	0.93	1.85	2.756 (5)	163

Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) x, y−1, z; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+3/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₆H₁₅NO₃)(C₃H₄N₂)]
M_r	396.08
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	11.5089 (11), 16.6194 (16), 18.9934 (19)
V (Å³)	3632.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.735, 0.772
No. of measured, independent and observed [I > 2σ(I)] reflections	18967, 6400, 4910
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.108, 1.02
No. of reflections	6400
No. of parameters	473
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.36
Absolute structure	Flack (1983), 2792 Friedel pairs [PLEASE CHECK]
Absolute structure parameter	−0.015 (16)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O1	1.805 (3)	Ni1—O2	1.852 (3)
Ni1—N1	1.833 (3)	Ni1—N2	1.900 (3)

O1—Ni1—N1	94.55 (15)	O1—Ni1—N2	89.98 (16)
O1—Ni1—O2	176.92 (16)	N1—Ni1—N2	173.95 (16)
N1—Ni1—O2	86.20 (15)	O2—Ni1—N2	89.49 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.93	2.59	3.476 (6)	158.5
C14—H14···O6ⁱⁱ	0.98	2.42	3.318 (6)	153.0
C18—H18···O6ⁱⁱⁱ	0.93	1.87	2.798 (5)	177.5
C37—H37···O3^iv	0.93	1.85	2.756 (5)	162.8

Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) x, y−1, z; (iii) −x+3/2, −y+1, z−1/2; (iv) −x+3/2, −y+1, z+1/2.

Weak Cg-Cg intermolecular interactions of (I) (Å) top

distance	Cg1—Cg10	Cg3—Cg9	Cg4—Cg7	Cg4—Cg9
centroid-centroid distance	3.940 (3)	3.709 (2)	3.526 (3)	3.932 (3)

Notes: CgI—CgJ = centroid-centroid distance between Plane I and J (Å); Cg1: Ni1/O2/C13/C12/N1; Cg3: Ni1/O1/C1/C10/C11/N1; Cg4: C1/C2/C3/C4/C9/C10; Cg7: Ni2/O5/C32/C31/N4; Cg9: Ni2/O4/C20/C29/C30/N4; Cg10: C20/C21/C22/C23/C28/C29.

Acknowledgements

This research was supported by the National Sciences Foundation of China (grant No. 20877036) and the Top-Class Foundation of Pingdingshan University (grant Nos. 2008012 and 2009001).

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