trans-Bis(5,5-diphenyl­hydantoinato-κN3)bis­(propane-1,2-diamine-κ2N,N′)nickel(II)

Hu, X.; Xu, X.; Wang, D.; Li, X.

doi:10.1107/S1600536808038749

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1636

doi:10.1107/S1600536808038749

Open

access

trans-Bis(5,5-diphenylhydantoinato-κN³)bis(propane-1,2-diamine-κ²N,N′)nickel(II)

Xilan Hu,^a ^* Xingyou Xu,^a Daqi Wang ^b and Xiaojiao Li ^a

^aHuaihai Institute of Technology, Jiangsu 222005, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: huxilan836@sohu.com

(Received 3 November 2008; accepted 19 November 2008; online 29 November 2008)

The asymmetric unit of the title complex, [Ni(pht)₂(pn)₂] (pht is 5,5-diphenylhydantoinate and pn is propane-1,2-diamine) or [Ni(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂], contains one-half [Ni(pht)₂(pn)₂] molecule. The Ni^II atom is situated on a crystallographic center of inversion and shows a distorted octahedral coordination geometry. A three-dimensional network structure is assembled by inter- and intramolecular N—H⋯O=C interactions.

Related literature

For general background see Akitsu et al. (1997 ), Milne et al. (1999 ). For related structures see Akitsu & Einaga et al. (2005 ); Hu et al. (2006a ,b ).

Experimental

Crystal data

[Ni(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]
M_r = 709.49
Triclinic, $[P \overline 1]$
a = 8.581 (1) Å
b = 9.731 (1) Å
c = 12.036 (2) Å
α = 100.602 (2)°
β = 90.298 (1)°
γ = 113.951 (2)°
V = 899.2 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 298 (2) K
0.47 × 0.45 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.769, T_max = 0.816
4760 measured reflections
3164 independent reflections
2908 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.09
3164 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3′B⋯O2	0.90	2.55	3.231 (2)	133
N4—H4A⋯O1	0.90	2.26	2.983 (2)	138

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S1600536808038749/im2088sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038749/im2088Isup2.hkl

checkCIF report

Comment top

5,5-Diphenylimidazoline-2,4-dione (Hpht) is a widely used drug in the treatment of epilepsy. It should also be an excellent ligand for transition metal complexes (Milne et al.,1999; Akitsu et al.,1997; Akitsu & Einaga, 2005). We have therefore designed and synthesized a series of complexes with 5,5-diphenylhydantoinato ligands (Hu et al., 2006a).

The title compound (Fig. 1) consists of a neutral [Ni(pht)₂(pn)₂] complex molecule. The nickel atom is situated at the crystallographic center of inversion and is coordinated by two nitrogen atoms from two pht ligands and four nitrogen atoms from two pn ligands. The metal atom therefore adopts a distorted octahedral NiN₆ coordination environment with a dihedral angle of 86.9 (1)° between N3—N3A—N4A—N4 and the hydantoin ring and dihedral angles between N3—N3A—N4A—N4 and the pht groups of 51.7 (1)° (C4 to C9) and 39.0 (1)° (C10 to C15), respectively. The Ni—N bond distances lie in the range of 2.096 (2) Å to 2.125 (2) Å. Intramolecular hydrogen bonds (Table 1) serve to stabilize the octahedral geometry. Adjacent molecules are linked by intermolecular hydrogen bonds along the crystallographic a axis. A similar hydrogen-bonding pattern is also found in the above-mentioned related complexes. The complex shows a three-dimensional network structure assembled by additional intermolecular N—H···O hydrogen bonds between the diamine ligand and the hydantoin ring.

Related literature top

For general background see Akitsu et al. (1997), Milne et al. (1999); for related structures see Akitsu & Einaga et al. (2005); Hu et al. (2006a,b).

Experimental top

To a solution of Hpht (1.00 mmol) in methanol (10 ml) was added Ni(OAc)₂ × 4 H₂O (0.5 mmol) and a solution of propane-1,2-diamine (1 mmol) in methanol (10 ml). Then the mixture was sealed in a 25 ml PTFE-lined stainless steel autoclave and heated to 423 K for 40 h, the fill rate being 80%. After cooling to room temperature, purple single crystals of the title compound were obtained by slow evaporation from the filtrate. Analysis, calculated for C₃₆H₄₂N₈NiO₄: C 61.66, H 6.01, N 16.26; found: C 60.94, H 5.97, N 15.78%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title complex.

trans-Bis(5,5-diphenylhydantoinato-κN³)bis(propane-1,2- diamine-κ²N,N')nickel(II) top

Crystal data top

[Ni(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]	Z = 1
M_r = 709.49	F(000) = 374
Triclinic, P1	D_x = 1.310 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.581 (1) Å	Cell parameters from 3393 reflections
b = 9.731 (1) Å	θ = 2.6–28.2°
c = 12.036 (2) Å	µ = 0.59 mm⁻¹
α = 100.602 (2)°	T = 298 K
β = 90.298 (1)°	Block, violet
γ = 113.951 (2)°	0.47 × 0.45 × 0.36 mm
V = 899.2 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3164 independent reflections
Radiation source: fine-focus sealed tube	2908 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
T_min = 0.769, T_max = 0.816	k = −11→11
4760 measured reflections	l = −14→14

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0351P)² + 0.2523P] where P = (F_o² + 2F_c²)/3
3164 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]	γ = 113.951 (2)°
M_r = 709.49	V = 899.2 (2) Å³
Triclinic, P1	Z = 1
a = 8.581 (1) Å	Mo Kα radiation
b = 9.731 (1) Å	µ = 0.59 mm⁻¹
c = 12.036 (2) Å	T = 298 K
α = 100.602 (2)°	0.47 × 0.45 × 0.36 mm
β = 90.298 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3164 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2908 reflections with I > 2σ(I)
T_min = 0.769, T_max = 0.816	R_int = 0.011
4760 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.09	Δρ_max = 0.17 e Å⁻³
3164 reflections	Δρ_min = −0.22 e Å⁻³
253 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	Occ. (<1)
Ni1	0.5000	0.5000	0.5000	0.02926 (10)
N1	0.09328 (19)	0.14829 (16)	0.62697 (11)	0.0390 (4)
H1	0.0097	0.0587	0.6140	0.047*
N2	0.31918 (17)	0.35330 (15)	0.59323 (11)	0.0327 (3)
N3	0.70216 (19)	0.52417 (18)	0.61129 (13)	0.0448 (4)
H3A	0.7766	0.6235	0.6302	0.054*	0.749 (12)
H3B	0.6617	0.4923	0.6751	0.054*	0.749 (12)
H3'A	0.7990	0.6047	0.6039	0.054*	0.251 (12)
H3'B	0.6766	0.5364	0.6839	0.054*	0.251 (12)
N4	0.5406 (2)	0.31168 (17)	0.41315 (13)	0.0426 (4)
H4A	0.4402	0.2291	0.3932	0.051*	0.749 (12)
H4B	0.5927	0.3333	0.3499	0.051*	0.749 (12)
H4'A	0.4581	0.2250	0.4272	0.051*	0.251 (12)
H4'B	0.5306	0.3081	0.3381	0.051*	0.251 (12)
O1	0.17051 (16)	0.14829 (14)	0.44533 (10)	0.0465 (3)
O2	0.39713 (17)	0.50006 (14)	0.77351 (10)	0.0473 (3)
C1	0.1917 (2)	0.21085 (18)	0.54757 (13)	0.0337 (4)
C2	0.3030 (2)	0.38406 (18)	0.70541 (13)	0.0329 (4)
C3	0.1457 (2)	0.25095 (18)	0.73787 (13)	0.0330 (4)
C4	0.0040 (2)	0.3011 (2)	0.77944 (14)	0.0368 (4)
C5	0.0355 (3)	0.4505 (2)	0.82802 (17)	0.0510 (5)
H5	0.1464	0.5265	0.8351	0.061*
C6	−0.0972 (3)	0.4891 (3)	0.86675 (19)	0.0635 (6)
H6	−0.0740	0.5905	0.8991	0.076*
C7	−0.2594 (3)	0.3800 (3)	0.85770 (19)	0.0650 (6)
H7	−0.3475	0.4064	0.8836	0.078*
C8	−0.2934 (3)	0.2302 (3)	0.8102 (2)	0.0712 (7)
H8	−0.4047	0.1551	0.8043	0.085*
C9	−0.1620 (3)	0.1901 (3)	0.7708 (2)	0.0582 (5)
H9	−0.1861	0.0884	0.7385	0.070*
C10	0.1974 (2)	0.1815 (2)	0.82832 (14)	0.0370 (4)
C11	0.2842 (3)	0.2747 (2)	0.93080 (16)	0.0503 (5)
H11	0.3119	0.3795	0.9434	0.060*
C12	0.3302 (3)	0.2147 (3)	1.01427 (19)	0.0684 (6)
H12	0.3890	0.2790	1.0822	0.082*
C13	0.2896 (4)	0.0616 (4)	0.9973 (2)	0.0843 (8)
H13	0.3212	0.0211	1.0533	0.101*
C14	0.2023 (4)	−0.0325 (3)	0.8978 (3)	0.0929 (9)
H14	0.1736	−0.1373	0.8866	0.112*
C15	0.1555 (3)	0.0270 (2)	0.8124 (2)	0.0637 (6)
H15	0.0961	−0.0381	0.7450	0.076*
C16	0.7858 (7)	0.4340 (8)	0.5562 (4)	0.0575 (12)	0.749 (12)
H16A	0.8554	0.4180	0.6118	0.069*	0.749 (12)
H16B	0.8602	0.4873	0.5032	0.069*	0.749 (12)
C17	0.6525 (7)	0.2805 (5)	0.4932 (5)	0.0575 (12)	0.749 (12)
H17	0.5812	0.2275	0.5487	0.069*	0.749 (12)
C18	0.7400 (14)	0.1808 (15)	0.4340 (10)	0.099 (3)	0.749 (12)
H18A	0.6551	0.0791	0.4038	0.148*	0.749 (12)
H18B	0.8197	0.1759	0.4877	0.148*	0.749 (12)
H18C	0.7999	0.2251	0.3734	0.148*	0.749 (12)
C16'	0.722 (2)	0.368 (2)	0.5724 (13)	0.056 (4)	0.251 (12)
H16C	0.8332	0.3810	0.6020	0.068*	0.251 (12)
H16D	0.6356	0.2892	0.6048	0.068*	0.251 (12)
C17'	0.7033 (17)	0.3156 (18)	0.4444 (14)	0.060 (3)	0.251 (12)
H17'	0.7959	0.3857	0.4081	0.072*	0.251 (12)
C18'	0.683 (4)	0.149 (5)	0.410 (3)	0.103 (8)	0.251 (12)
H18D	0.5901	0.0839	0.4465	0.154*	0.251 (12)
H18E	0.7867	0.1422	0.4322	0.154*	0.251 (12)
H18F	0.6582	0.1151	0.3289	0.154*	0.251 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02461 (16)	0.02656 (16)	0.02889 (16)	0.00303 (12)	0.00163 (11)	0.00520 (11)
N1	0.0362 (8)	0.0296 (7)	0.0283 (7)	−0.0070 (6)	0.0060 (6)	0.0005 (6)
N2	0.0296 (7)	0.0271 (7)	0.0285 (7)	−0.0002 (6)	0.0031 (6)	0.0033 (5)
N3	0.0354 (8)	0.0493 (9)	0.0422 (8)	0.0079 (7)	−0.0019 (7)	0.0143 (7)
N4	0.0407 (9)	0.0342 (8)	0.0462 (9)	0.0099 (7)	0.0075 (7)	0.0059 (7)
O1	0.0454 (8)	0.0378 (7)	0.0282 (6)	−0.0079 (6)	0.0059 (5)	−0.0010 (5)
O2	0.0453 (7)	0.0366 (7)	0.0329 (6)	−0.0059 (6)	0.0031 (6)	−0.0030 (5)
C1	0.0311 (9)	0.0292 (8)	0.0301 (8)	0.0024 (7)	0.0034 (7)	0.0046 (7)
C2	0.0304 (9)	0.0290 (8)	0.0304 (8)	0.0039 (7)	0.0031 (7)	0.0048 (7)
C3	0.0313 (9)	0.0295 (8)	0.0272 (8)	0.0025 (7)	0.0038 (7)	0.0032 (6)
C4	0.0355 (9)	0.0441 (10)	0.0297 (8)	0.0134 (8)	0.0061 (7)	0.0119 (7)
C5	0.0467 (11)	0.0520 (12)	0.0472 (11)	0.0180 (10)	0.0040 (9)	−0.0008 (9)
C6	0.0677 (16)	0.0705 (15)	0.0572 (13)	0.0382 (13)	0.0098 (11)	0.0017 (11)
C7	0.0620 (15)	0.0929 (19)	0.0575 (13)	0.0471 (14)	0.0196 (11)	0.0201 (13)
C8	0.0395 (12)	0.0841 (18)	0.0908 (18)	0.0206 (12)	0.0208 (12)	0.0308 (15)
C9	0.0409 (11)	0.0533 (12)	0.0777 (15)	0.0136 (10)	0.0168 (11)	0.0209 (11)
C10	0.0328 (9)	0.0395 (9)	0.0354 (9)	0.0107 (8)	0.0108 (7)	0.0102 (7)
C11	0.0544 (12)	0.0543 (12)	0.0382 (10)	0.0192 (10)	0.0011 (9)	0.0078 (9)
C12	0.0703 (16)	0.0855 (18)	0.0460 (12)	0.0272 (14)	−0.0034 (11)	0.0173 (12)
C13	0.099 (2)	0.096 (2)	0.0688 (17)	0.0404 (18)	−0.0025 (15)	0.0412 (16)
C14	0.125 (3)	0.0590 (16)	0.100 (2)	0.0353 (17)	0.000 (2)	0.0359 (16)
C15	0.0815 (17)	0.0425 (12)	0.0592 (13)	0.0169 (11)	−0.0027 (12)	0.0126 (10)
C16	0.041 (2)	0.068 (3)	0.067 (2)	0.024 (2)	−0.0031 (18)	0.021 (2)
C17	0.064 (3)	0.054 (2)	0.067 (3)	0.036 (2)	0.009 (2)	0.0153 (19)
C18	0.106 (7)	0.102 (6)	0.111 (5)	0.081 (6)	−0.013 (4)	−0.014 (4)
C16'	0.053 (9)	0.054 (8)	0.071 (8)	0.031 (7)	−0.006 (6)	0.014 (7)
C17'	0.051 (6)	0.080 (8)	0.064 (8)	0.039 (6)	0.019 (5)	0.021 (6)
C18'	0.085 (16)	0.099 (18)	0.14 (2)	0.063 (15)	−0.022 (13)	0.007 (15)

Geometric parameters (Å, º) top

Ni1—N3ⁱ	2.0946 (15)	C6—H6	0.9300
Ni1—N3	2.0946 (15)	C7—C8	1.371 (4)
Ni1—N4	2.0950 (15)	C7—H7	0.9300
Ni1—N4ⁱ	2.0950 (15)	C8—C9	1.394 (3)
Ni1—N2ⁱ	2.1245 (13)	C8—H8	0.9300
Ni1—N2	2.1245 (13)	C9—H9	0.9300
N1—C1	1.343 (2)	C10—C15	1.372 (3)
N1—C3	1.456 (2)	C10—C11	1.389 (3)
N1—H1	0.8600	C11—C12	1.380 (3)
N2—C2	1.349 (2)	C11—H11	0.9300
N2—C1	1.379 (2)	C12—C13	1.359 (4)
N3—C16	1.423 (5)	C12—H12	0.9300
N3—C16'	1.580 (13)	C13—C14	1.366 (4)
N3—H3A	0.9000	C13—H13	0.9300
N3—H3B	0.9000	C14—C15	1.398 (3)
N3—H3'A	0.9000	C14—H14	0.9300
N3—H3'B	0.9000	C15—H15	0.9300
N4—C17'	1.428 (11)	C16—C17	1.517 (8)
N4—C17	1.510 (4)	C16—H16A	0.9700
N4—H4A	0.9000	C16—H16B	0.9700
N4—H4B	0.9000	C17—C18	1.534 (11)
N4—H4'A	0.9000	C17—H17	0.9800
N4—H4'B	0.9000	C18—H18A	0.9600
O1—C1	1.245 (2)	C18—H18B	0.9600
O2—C2	1.2292 (19)	C18—H18C	0.9600
C2—C3	1.557 (2)	C16'—C17'	1.52 (3)
C3—C10	1.532 (2)	C16'—H16C	0.9700
C3—C4	1.538 (2)	C16'—H16D	0.9700
C4—C5	1.377 (3)	C17'—C18'	1.54 (4)
C4—C9	1.383 (3)	C17'—H17'	0.9800
C5—C6	1.393 (3)	C18'—H18D	0.9600
C5—H5	0.9300	C18'—H18E	0.9600
C6—C7	1.354 (3)	C18'—H18F	0.9600

N3ⁱ—Ni1—N3	180.000 (1)	C10—C3—C4	109.20 (13)
N3ⁱ—Ni1—N4	96.99 (6)	N1—C3—C2	98.65 (12)
N3—Ni1—N4	83.01 (6)	C10—C3—C2	111.63 (14)
N3ⁱ—Ni1—N4ⁱ	83.01 (6)	C4—C3—C2	112.68 (14)
N3—Ni1—N4ⁱ	96.99 (6)	C5—C4—C9	118.46 (18)
N4—Ni1—N4ⁱ	180.00 (8)	C5—C4—C3	123.02 (16)
N3ⁱ—Ni1—N2ⁱ	90.86 (6)	C9—C4—C3	118.48 (17)
N3—Ni1—N2ⁱ	89.14 (6)	C4—C5—C6	120.7 (2)
N4—Ni1—N2ⁱ	90.56 (6)	C4—C5—H5	119.7
N4ⁱ—Ni1—N2ⁱ	89.44 (6)	C6—C5—H5	119.7
N3ⁱ—Ni1—N2	89.14 (6)	C7—C6—C5	120.5 (2)
N3—Ni1—N2	90.86 (6)	C7—C6—H6	119.7
N4—Ni1—N2	89.44 (6)	C5—C6—H6	119.7
N4ⁱ—Ni1—N2	90.56 (6)	C6—C7—C8	119.7 (2)
N2ⁱ—Ni1—N2	180.00 (7)	C6—C7—H7	120.1
C1—N1—C3	111.57 (13)	C8—C7—H7	120.1
C1—N1—H1	124.2	C7—C8—C9	120.3 (2)
C3—N1—H1	124.2	C7—C8—H8	119.8
C2—N2—C1	107.79 (13)	C9—C8—H8	119.8
C2—N2—Ni1	126.79 (11)	C4—C9—C8	120.2 (2)
C1—N2—Ni1	125.37 (10)	C4—C9—H9	119.9
C16—N3—C16'	26.9 (6)	C8—C9—H9	119.9
C16—N3—Ni1	108.5 (2)	C15—C10—C11	118.31 (18)
C16'—N3—Ni1	103.2 (5)	C15—C10—C3	121.58 (17)
C16—N3—H3A	110.0	C11—C10—C3	120.09 (16)
C16'—N3—H3A	134.1	C12—C11—C10	121.2 (2)
Ni1—N3—H3A	110.0	C12—C11—H11	119.4
C16—N3—H3B	110.0	C10—C11—H11	119.4
C16'—N3—H3B	88.1	C13—C12—C11	120.0 (2)
Ni1—N3—H3B	110.0	C13—C12—H12	120.0
H3A—N3—H3B	108.4	C11—C12—H12	120.0
C16—N3—H3'A	84.6	C12—C13—C14	119.7 (2)
C16'—N3—H3'A	110.8	C12—C13—H13	120.1
Ni1—N3—H3'A	111.2	C14—C13—H13	120.1
H3A—N3—H3'A	27.1	C13—C14—C15	120.8 (2)
H3B—N3—H3'A	128.4	C13—C14—H14	119.6
C16—N3—H3'B	128.8	C15—C14—H14	119.6
C16'—N3—H3'B	111.3	C10—C15—C14	119.9 (2)
Ni1—N3—H3'B	111.2	C10—C15—H15	120.0
H3A—N3—H3'B	85.3	C14—C15—H15	120.0
H3B—N3—H3'B	24.9	N3—C16—C17	109.4 (4)
H3'A—N3—H3'B	109.1	N3—C16—H16A	109.8
C17'—N4—C17	30.6 (6)	C17—C16—H16A	109.8
C17'—N4—Ni1	113.6 (5)	N3—C16—H16B	109.8
C17—N4—Ni1	106.75 (19)	C17—C16—H16B	109.8
C17'—N4—H4A	128.2	H16A—C16—H16B	108.2
C17—N4—H4A	110.4	N4—C17—C16	107.8 (4)
Ni1—N4—H4A	110.4	N4—C17—C18	113.7 (5)
C17'—N4—H4B	80.3	C16—C17—C18	110.2 (6)
C17—N4—H4B	110.4	N4—C17—H17	108.3
Ni1—N4—H4B	110.4	C16—C17—H17	108.3
H4A—N4—H4B	108.6	C18—C17—H17	108.3
C17'—N4—H4'A	108.7	C17'—C16'—N3	113.0 (12)
C17—N4—H4'A	84.0	C17'—C16'—H16C	109.0
Ni1—N4—H4'A	108.7	N3—C16'—H16C	109.0
H4A—N4—H4'A	29.0	C17'—C16'—H16D	109.0
H4B—N4—H4'A	131.5	N3—C16'—H16D	109.0
C17'—N4—H4'B	109.2	H16C—C16'—H16D	107.8
C17—N4—H4'B	136.1	N4—C17'—C16'	102.5 (12)
Ni1—N4—H4'B	108.9	N4—C17'—C18'	105.2 (14)
H4A—N4—H4'B	80.1	C16'—C17'—C18'	112 (2)
H4B—N4—H4'B	31.9	N4—C17'—H17'	112.3
H4'A—N4—H4'B	107.6	C16'—C17'—H17'	112.3
O1—C1—N1	124.25 (15)	C18'—C17'—H17'	112.3
O1—C1—N2	124.13 (14)	C17'—C18'—H18D	109.5
N1—C1—N2	111.62 (13)	C17'—C18'—H18E	109.5
O2—C2—N2	125.70 (15)	H18D—C18'—H18E	109.5
O2—C2—C3	124.01 (14)	C17'—C18'—H18F	109.5
N2—C2—C3	110.29 (13)	H18D—C18'—H18F	109.5
N1—C3—C10	113.28 (14)	H18E—C18'—H18F	109.5
N1—C3—C4	111.15 (14)

N3ⁱ—Ni1—N2—C2	−125.79 (15)	O2—C2—C3—C4	65.1 (2)
N3—Ni1—N2—C2	54.21 (15)	N2—C2—C3—C4	−114.64 (15)
N4—Ni1—N2—C2	137.22 (15)	N1—C3—C4—C5	−135.47 (17)
N4ⁱ—Ni1—N2—C2	−42.78 (15)	C10—C3—C4—C5	98.84 (19)
N2ⁱ—Ni1—N2—C2	4 (100)	C2—C3—C4—C5	−25.8 (2)
N3ⁱ—Ni1—N2—C1	51.22 (14)	N1—C3—C4—C9	46.6 (2)
N3—Ni1—N2—C1	−128.78 (14)	C10—C3—C4—C9	−79.1 (2)
N4—Ni1—N2—C1	−45.78 (14)	C2—C3—C4—C9	156.21 (17)
N4ⁱ—Ni1—N2—C1	134.22 (14)	C9—C4—C5—C6	−0.5 (3)
N2ⁱ—Ni1—N2—C1	−179 (100)	C3—C4—C5—C6	−178.45 (18)
N3ⁱ—Ni1—N3—C16	122 (100)	C4—C5—C6—C7	0.3 (3)
N4—Ni1—N3—C16	15.4 (3)	C5—C6—C7—C8	0.1 (4)
N4ⁱ—Ni1—N3—C16	−164.6 (3)	C6—C7—C8—C9	−0.4 (4)
N2ⁱ—Ni1—N3—C16	−75.2 (3)	C5—C4—C9—C8	0.3 (3)
N2—Ni1—N3—C16	104.8 (3)	C3—C4—C9—C8	178.32 (19)
N3ⁱ—Ni1—N3—C16'	95 (100)	C7—C8—C9—C4	0.2 (4)
N4—Ni1—N3—C16'	−12.0 (8)	N1—C3—C10—C15	−15.7 (2)
N4ⁱ—Ni1—N3—C16'	168.0 (8)	C4—C3—C10—C15	108.7 (2)
N2ⁱ—Ni1—N3—C16'	−102.7 (8)	C2—C3—C10—C15	−126.00 (19)
N2—Ni1—N3—C16'	77.3 (8)	N1—C3—C10—C11	166.25 (16)
N3ⁱ—Ni1—N4—C17'	162.2 (9)	C4—C3—C10—C11	−69.3 (2)
N3—Ni1—N4—C17'	−17.8 (9)	C2—C3—C10—C11	56.0 (2)
N4ⁱ—Ni1—N4—C17'	−110 (100)	C15—C10—C11—C12	1.0 (3)
N2ⁱ—Ni1—N4—C17'	71.3 (9)	C3—C10—C11—C12	179.14 (19)
N2—Ni1—N4—C17'	−108.7 (9)	C10—C11—C12—C13	−0.4 (4)
N3ⁱ—Ni1—N4—C17	−165.9 (3)	C11—C12—C13—C14	−0.4 (5)
N3—Ni1—N4—C17	14.1 (3)	C12—C13—C14—C15	0.7 (5)
N4ⁱ—Ni1—N4—C17	−78 (100)	C11—C10—C15—C14	−0.8 (4)
N2ⁱ—Ni1—N4—C17	103.1 (3)	C3—C10—C15—C14	−178.9 (2)
N2—Ni1—N4—C17	−76.9 (3)	C13—C14—C15—C10	0.0 (5)
C3—N1—C1—O1	−177.93 (17)	C16'—N3—C16—C17	40.6 (13)
C3—N1—C1—N2	1.9 (2)	Ni1—N3—C16—C17	−42.2 (6)
C2—N2—C1—O1	179.86 (17)	C17'—N4—C17—C16	68.4 (11)
Ni1—N2—C1—O1	2.4 (3)	Ni1—N4—C17—C16	−39.8 (6)
C2—N2—C1—N1	0.0 (2)	C17'—N4—C17—C18	−54.1 (13)
Ni1—N2—C1—N1	−177.47 (11)	Ni1—N4—C17—C18	−162.3 (7)
C1—N2—C2—O2	178.50 (18)	N3—C16—C17—N4	55.9 (7)
Ni1—N2—C2—O2	−4.1 (3)	N3—C16—C17—C18	−179.5 (6)
C1—N2—C2—C3	−1.79 (19)	C16—N3—C16'—C17'	−64.1 (18)
Ni1—N2—C2—C3	175.64 (10)	Ni1—N3—C16'—C17'	40.7 (17)
C1—N1—C3—C10	−120.79 (16)	C17—N4—C17'—C16'	−40.9 (13)
C1—N1—C3—C4	115.83 (16)	Ni1—N4—C17'—C16'	42.2 (18)
C1—N1—C3—C2	−2.67 (18)	C17—N4—C17'—C18'	76 (2)
O2—C2—C3—N1	−177.60 (17)	Ni1—N4—C17'—C18'	159.0 (19)
N2—C2—C3—N1	2.68 (18)	N3—C16'—C17'—N4	−55 (2)
O2—C2—C3—C10	−58.2 (2)	N3—C16'—C17'—C18'	−167.3 (14)
N2—C2—C3—C10	122.05 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3′B···O2	0.90	2.55	3.231 (2)	133
N4—H4A···O1	0.90	2.26	2.983 (2)	138

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₁N₂O₂)₂(C₃H₁₀N₂)₂]
M_r	709.49
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.581 (1), 9.731 (1), 12.036 (2)
α, β, γ (°)	100.602 (2), 90.298 (1), 113.951 (2)
V (Å³)	899.2 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.47 × 0.45 × 0.36

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.769, 0.816
No. of measured, independent and observed [I > 2σ(I)] reflections	4760, 3164, 2908
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.075, 1.09
No. of reflections	3164
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N3—H3'B···O2	0.90	2.55	3.231 (2)	132.6
N4—H4A···O1	0.90	2.26	2.983 (2)	137.8

Acknowledgements

We are grateful for financial support from the Key Project for Fundamental Research of the Educational Committee of Jiangsu Province (07 K J A15011) and the Natural Science Foundation of Huaihai Institute of Technology (KX07042).

References

Akitsu, T. & Einaga, Y. (2005). Acta Cryst. C61, m183–m186. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akitsu, T., Komorita, S., Kushi, Y., Li, C., Kanehisa, N. & Kai, Y. (1997). Bull. Chem. Soc. Jpn, 70, 821–827. CrossRef CAS Web of Science Google Scholar
Hu, X.-L., Xu, X.-Y., Wang, D.-Q. & Xu, T.-T. (2006a). Acta Cryst. E62, m1922–m1923. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, X., Xu, X., Xu, T. & Wang, D. (2006b). Acta Cryst. E62, m2221–m2223. Web of Science CSD CrossRef IUCr Journals Google Scholar
Milne, P., Ho, M. & Weaver, D. F. (1999). J. Mol. Struct. (Theochem), 492, 19–28. Web of Science CrossRef CAS 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.