Bis[2-(benzyl­amino)­pyridine-κN1]bis­(2-formyl­phenolato-κ2O,O′)nickel(II)

Ayikoé, K.; Butcher, R.J.; Gultneh, Y.

doi:10.1107/S1600536811001425

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m207-m208

doi:10.1107/S1600536811001425

Open

access

Bis[2-(benzylamino)pyridine-κN¹]bis(2-formylphenolato-κ²O,O′)nickel(II)

Kouassi Ayikoé,^a Ray J. Butcher ^a ^* and Yilma Gultneh ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 8 December 2010; accepted 10 January 2011; online 15 January 2011)

In the title complex, [Ni(C₇H₅O₂)₂(C₁₂H₁₂N₂)₂], the Ni^II atom lies on a center of inversion and is coordinated in an octahedral geometry by two 2-(benzylamino)pyridine (2-BAP) and two 2-formylphenolate ligands with the O-atom donors in the equatorial plane and the pyridine N atoms in axial positions. There are hydrogen-bonding interactions between the secondary amine H atom and the phenolate O atom, as well as C—H⋯O interactions, which result in the dihedral angle between the aromatic phenyl ring of the 2-formylphenolate moiety and the pyridine ring being 80.23 (4)°. In the packing, there are both C—H⋯π interactions, which link the molecules into chains along the b axis, and offset π–π interactions involving both the pyridine and phenyl rings of the 2-BAP ligands [centroid–centroid distances = 4.0100 (8) Å for the pyridine rings and 3.6601 (8) and 4.8561 (8) Å for the phenyl rings].

Related literature

For the structures of similar octahedral nickel complexes, see: Assey et al. (2010a ,b ); Butcher et al. (2009 ); Gultneh et al. (2008 ). For bond-length data, Allen et al. (1987 ).

Experimental

Crystal data

[Ni(C₇H₅O₂)₂(C₁₂H₁₂N₂)₂]
M_r = 669.40
Triclinic, $[P \overline 1]$
a = 8.1747 (5) Å
b = 9.3365 (5) Å
c = 10.9183 (6) Å
α = 73.926 (5)°
β = 84.766 (5)°
γ = 77.247 (5)°
V = 780.58 (8) Å³
Z = 1
Mo Kα radiation
μ = 0.67 mm⁻¹
T = 110 K
0.47 × 0.41 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.932, T_max = 1.000
9822 measured reflections
5136 independent reflections
4216 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.086
S = 1.05
5136 reflections
218 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C1A–C6A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2B—H2BN⋯O1A	0.775 (17)	2.147 (18)	2.8550 (14)	152.0 (17)
C1B—H1BA⋯O1Aⁱ	0.95	2.42	2.9216 (14)	113
C3B—H3BA⋯Cg4ⁱⁱ	0.95	2.44	3.3674 (14)	166
C11B—H11A⋯Cg4ⁱⁱⁱ	0.95	2.91	3.7535 (17)	148
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811001425/zl2338sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001425/zl2338Isup2.hkl

checkCIF report

Comment top

As part of our continuing studies (Gultneh et al. 2008; Assey et al., 2010a, 2010b; Butcher et al., 2009) of nickel(II) complexes with relevance to the nickel containing metalloenzymes, we wish to report the structure of the mixed ligand complex, C₃₈H₃₄N₄NiO₄, where the Ni lies on a center of inversion and contains two 2-benzylaminopyridine (2-BAP) and two salicylaldehyde molecules where the O donors form an equatorial plane with pyridine N's in axial positions, thus the Ni is in an octahedral coordination environment.

The Ni—O and Ni—N bond distances (see Table 1) are within the normal ranges observed in other Ni complexes containing similar ligands (Allen et al., 1987). There are hydrogen bonding interactions between the secondary amine H and phenolic O as well as C—H···O interactions which result in the dihedral angle between the aromatic phenyl ring of the salicylaldehyde moiety and the pyridine ring being 80.23 (4)°. The dihedral angle between the NiO₄ plane and salicylaldehyde plane is 10.31 (5)°. In the packing there are both intermolecular C-H···π interactions (see Table 1) involving the salicylaldehyde anion which link the molecules into a chain in the b direction. In addition there are offsetting π–π interactions involving both the pyridine and phenyl rings of the 2-BAP moiety (see Figure 3). For the pyridine rings, Cg–Cg distance 4.0100 (8), perpendicular distance 3.3506 (5), slippage 2.203 Symmetry 1-x, 1-y, 1-z; for the phenyl rings (a) Cg-Cg -distance 3.6601 (8), perpendicular distance 3.4408 (5), slippage 1.248 Symmetry -x, 1-y, 2-z; (b) Cg–Cg distance 4.8561 (8), perpendicular distance 3.0743 (5), slippage 3.759 Symmetry 1-x, 1-y, 2-z.

Related literature top

For the structures of similar octahedral nickel complexes, see: Assey et al. (2010a,b); Butcher et al. (2009); Gultneh et al. (2008). For bond-length data, Allen et al. (1987).

Experimental top

Salicylaldehyde (0.23 g, 1.9 mmol) and 0.370 g of 2-benzylaminopyridine (2.0 mmol) were separately dissolved in 20 ml and 30 ml of methanol respectively before mixing and stirring under reflux followed by addition of 0.36 g (1.5 mmol) of NiCl₂.6H₂O in MeOH (20 ml). 2-Benzylaminopyridine, a secondary amine, has shown a chelating ability to nickel salts (nitrate and perchlorate) even in the presence of an aryl aldehyde (Butcher et al., 2009). The solution of the salt and the two ligands was stirred overnight at room temperature. The mixture was evaporated under reduced pressure and a dark-green semi-solid was obtained. A small amount of the complex was then dissolved in 5 ml of DMF, filtered and layered with diethyl ether. Light green X-ray quality crystals were obtained after slow diffusion of the diethyl ether into DMF (yield 68%, m.p. 410 - 412 K). IR Data: 3330 cm^-1 ν(N—H) benzylamine nitrogen-hydrogen stretching; 3078 cm^-1 and 3018 cm^-1 ν(C—H) aldehyde C—H stretching; 2851 cm^-1 and 2770 cm^-1 benzyl ν(C—H); 1615 cm^-1 ν(C=O) aldehyde carbonyl stretching; 1533 cm^-1 and 1516 cm^-1 ν(N—C) and ν(N—H) bendings respectively; 1471 cm^-1, 1445 cm^-1 v(Ar C—H) bendings; 757 cm^-1 ν (out of plane aromatic bend). UV-vis data (in cm^-1 with ε_max [M^-1.cm^-1] in brackets): 32154 (1847), 25510 (1306), 15476 (13), and 9174 (7). Room temperature magnetic moment was 3.01 BM.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 complex, C₃₈H₃₄N₄NiO₄, showing the atom numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. The molecular packing for C₃₈H₃₄N₄NiO₄, viewed down the c axis showing the intramolecular N—H···O interactions as dashed lines.
	Fig. 3. Molecular packing for C₃₈H₃₄N₄NiO₄ showing π–π and C-H···π interactions.

Bis[2-(benzylamino)pyridine-κN¹]bis(2-formylphenolato- κ²O,O')nickel(II) top

Crystal data top

[Ni(C₇H₅O₂)₂(C₁₂H₁₂N₂)₂]	Z = 1
M_r = 669.40	F(000) = 350
Triclinic, P1	D_x = 1.424 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1747 (5) Å	Cell parameters from 5541 reflections
b = 9.3365 (5) Å	θ = 4.8–32.6°
c = 10.9183 (6) Å	µ = 0.67 mm⁻¹
α = 73.926 (5)°	T = 110 K
β = 84.766 (5)°	Block, pale green
γ = 77.247 (5)°	0.47 × 0.41 × 0.35 mm
V = 780.58 (8) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector	5136 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4216 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.6°, θ_min = 4.8°
ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→13
T_min = 0.932, T_max = 1.000	l = −16→15
9822 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0457P)²] where P = (F_o² + 2F_c²)/3
5136 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Ni(C₇H₅O₂)₂(C₁₂H₁₂N₂)₂]	γ = 77.247 (5)°
M_r = 669.40	V = 780.58 (8) Å³
Triclinic, P1	Z = 1
a = 8.1747 (5) Å	Mo Kα radiation
b = 9.3365 (5) Å	µ = 0.67 mm⁻¹
c = 10.9183 (6) Å	T = 110 K
α = 73.926 (5)°	0.47 × 0.41 × 0.35 mm
β = 84.766 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector	5136 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	4216 reflections with I > 2σ(I)
T_min = 0.932, T_max = 1.000	R_int = 0.025
9822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.46 e Å⁻³
5136 reflections	Δρ_min = −0.27 e Å⁻³
218 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
Ni	0.5000	1.0000	0.5000	0.01289 (7)
O1A	0.27528 (11)	1.00213 (9)	0.43885 (9)	0.01507 (18)
O2A	0.61193 (11)	0.98245 (10)	0.32627 (9)	0.01674 (18)
C1A	0.24508 (15)	0.97081 (12)	0.33607 (12)	0.0140 (2)
C2A	0.07923 (16)	0.95941 (13)	0.31617 (13)	0.0172 (2)
H2AA	−0.0068	0.9765	0.3782	0.021*
C3A	0.04021 (17)	0.92416 (14)	0.20916 (14)	0.0213 (3)
H3AA	−0.0721	0.9184	0.1990	0.026*
C4A	0.16279 (18)	0.89655 (14)	0.11473 (14)	0.0221 (3)
H4AA	0.1346	0.8713	0.0419	0.026*
C5A	0.32436 (17)	0.90699 (14)	0.13020 (13)	0.0190 (3)
H5AA	0.4081	0.8885	0.0670	0.023*
C6A	0.36945 (16)	0.94477 (13)	0.23829 (12)	0.0150 (2)
C7A	0.54127 (16)	0.95393 (13)	0.24225 (12)	0.0172 (2)
H7A	0.6106	0.9358	0.1712	0.021*
N1B	0.55584 (13)	0.75527 (11)	0.56185 (10)	0.0146 (2)
N2B	0.28723 (13)	0.72549 (12)	0.63564 (11)	0.0173 (2)
H2BN	0.262 (2)	0.8111 (19)	0.6004 (18)	0.026 (4)*
C1B	0.71914 (16)	0.69158 (14)	0.54563 (13)	0.0166 (2)
H1BA	0.7937	0.7570	0.5059	0.020*
C2B	0.78339 (16)	0.53754 (14)	0.58336 (13)	0.0168 (2)
H2BA	0.8998	0.4981	0.5729	0.020*
C3B	0.67321 (16)	0.44103 (13)	0.63735 (12)	0.0165 (2)
H3BA	0.7134	0.3339	0.6621	0.020*
C4B	0.50697 (16)	0.50075 (13)	0.65462 (12)	0.0150 (2)
H4BA	0.4310	0.4356	0.6915	0.018*
C5B	0.44918 (15)	0.66092 (13)	0.61691 (12)	0.0139 (2)
C6B	0.16081 (15)	0.63865 (14)	0.69494 (13)	0.0172 (2)
H6BA	0.1547	0.5660	0.6453	0.021*
H6BB	0.0503	0.7091	0.6912	0.021*
C7B	0.19397 (15)	0.55083 (14)	0.83287 (13)	0.0167 (2)
C8B	0.26795 (17)	0.60818 (16)	0.91340 (14)	0.0221 (3)
H8BA	0.2980	0.7048	0.8822	0.027*
C9B	0.29842 (19)	0.52611 (18)	1.03870 (15)	0.0295 (3)
H9BA	0.3482	0.5672	1.0929	0.035*
C10B	0.25672 (19)	0.38432 (18)	1.08552 (15)	0.0313 (3)
H10A	0.2794	0.3275	1.1711	0.038*
C11B	0.1819 (2)	0.32658 (16)	1.00657 (16)	0.0294 (3)
H11A	0.1515	0.2302	1.0383	0.035*
C12B	0.15109 (17)	0.40869 (15)	0.88107 (14)	0.0222 (3)
H12A	0.1002	0.3677	0.8274	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.01303 (11)	0.01272 (11)	0.01305 (12)	−0.00388 (8)	−0.00051 (8)	−0.00262 (8)
O1A	0.0149 (4)	0.0147 (4)	0.0160 (4)	−0.0035 (3)	−0.0011 (3)	−0.0040 (3)
O2A	0.0159 (4)	0.0184 (4)	0.0162 (5)	−0.0050 (3)	−0.0002 (3)	−0.0040 (3)
C1A	0.0162 (6)	0.0083 (5)	0.0158 (6)	−0.0020 (4)	−0.0039 (5)	0.0001 (4)
C2A	0.0148 (6)	0.0146 (5)	0.0212 (6)	−0.0012 (5)	−0.0035 (5)	−0.0036 (5)
C3A	0.0193 (6)	0.0186 (6)	0.0268 (7)	−0.0031 (5)	−0.0088 (5)	−0.0055 (5)
C4A	0.0286 (7)	0.0193 (6)	0.0191 (7)	−0.0036 (5)	−0.0097 (6)	−0.0043 (5)
C5A	0.0246 (7)	0.0174 (5)	0.0139 (6)	−0.0046 (5)	−0.0023 (5)	−0.0017 (5)
C6A	0.0177 (6)	0.0123 (5)	0.0144 (6)	−0.0040 (5)	−0.0018 (5)	−0.0011 (4)
C7A	0.0193 (6)	0.0172 (5)	0.0137 (6)	−0.0048 (5)	0.0009 (5)	−0.0012 (5)
N1B	0.0143 (5)	0.0147 (4)	0.0150 (5)	−0.0045 (4)	0.0000 (4)	−0.0032 (4)
N2B	0.0144 (5)	0.0126 (5)	0.0219 (6)	−0.0035 (4)	0.0008 (4)	0.0005 (4)
C1B	0.0155 (6)	0.0175 (5)	0.0179 (6)	−0.0059 (5)	0.0017 (5)	−0.0050 (5)
C2B	0.0139 (6)	0.0184 (5)	0.0174 (6)	−0.0010 (5)	0.0014 (5)	−0.0060 (5)
C3B	0.0207 (6)	0.0136 (5)	0.0143 (6)	−0.0016 (5)	−0.0009 (5)	−0.0036 (4)
C4B	0.0177 (6)	0.0128 (5)	0.0140 (6)	−0.0047 (5)	0.0002 (5)	−0.0016 (4)
C5B	0.0148 (5)	0.0146 (5)	0.0127 (6)	−0.0042 (4)	−0.0009 (4)	−0.0032 (4)
C6B	0.0141 (6)	0.0182 (5)	0.0197 (6)	−0.0066 (5)	0.0000 (5)	−0.0032 (5)
C7B	0.0132 (5)	0.0170 (5)	0.0188 (6)	−0.0024 (5)	0.0024 (5)	−0.0043 (5)
C8B	0.0208 (6)	0.0264 (6)	0.0209 (7)	−0.0069 (5)	0.0020 (5)	−0.0086 (5)
C9B	0.0260 (7)	0.0431 (8)	0.0207 (7)	−0.0039 (7)	−0.0005 (6)	−0.0129 (7)
C10B	0.0258 (7)	0.0380 (8)	0.0187 (7)	0.0049 (6)	0.0035 (6)	0.0006 (6)
C11B	0.0301 (8)	0.0211 (6)	0.0287 (8)	−0.0029 (6)	0.0079 (7)	0.0023 (6)
C12B	0.0216 (6)	0.0186 (6)	0.0253 (7)	−0.0058 (5)	0.0031 (6)	−0.0040 (5)

Geometric parameters (Å, º) top

Ni—O1A	2.0052 (9)	N2B—H2BN	0.775 (17)
Ni—O1Aⁱ	2.0052 (9)	C1B—C2B	1.3755 (17)
Ni—O2A	2.0618 (9)	C1B—H1BA	0.9500
Ni—O2Aⁱ	2.0618 (9)	C2B—C3B	1.3920 (17)
Ni—N1Bⁱ	2.1509 (10)	C2B—H2BA	0.9500
Ni—N1B	2.1509 (10)	C3B—C4B	1.3676 (18)
O1A—C1A	1.2923 (15)	C3B—H3BA	0.9500
O2A—C7A	1.2434 (15)	C4B—C5B	1.4184 (16)
C1A—C2A	1.4237 (17)	C4B—H4BA	0.9500
C1A—C6A	1.4384 (18)	C6B—C7B	1.5187 (19)
C2A—C3A	1.3793 (18)	C6B—H6BA	0.9900
C2A—H2AA	0.9500	C6B—H6BB	0.9900
C3A—C4A	1.406 (2)	C7B—C8B	1.3878 (18)
C3A—H3AA	0.9500	C7B—C12B	1.3950 (17)
C4A—C5A	1.3745 (19)	C8B—C9B	1.385 (2)
C4A—H4AA	0.9500	C8B—H8BA	0.9500
C5A—C6A	1.4214 (17)	C9B—C10B	1.387 (2)
C5A—H5AA	0.9500	C9B—H9BA	0.9500
C6A—C7A	1.4311 (18)	C10B—C11B	1.381 (2)
C7A—H7A	0.9500	C10B—H10A	0.9500
N1B—C1B	1.3534 (16)	C11B—C12B	1.387 (2)
N1B—C5B	1.3594 (15)	C11B—H11A	0.9500
N2B—C5B	1.3507 (16)	C12B—H12A	0.9500
N2B—C6B	1.4497 (15)

O1A—Ni—O1Aⁱ	180.000 (1)	C5B—N2B—H2BN	114.7 (13)
O1A—Ni—O2A	90.90 (4)	C6B—N2B—H2BN	120.9 (13)
O1Aⁱ—Ni—O2A	89.10 (4)	N1B—C1B—C2B	123.78 (11)
O1A—Ni—O2Aⁱ	89.10 (4)	N1B—C1B—H1BA	118.1
O1Aⁱ—Ni—O2Aⁱ	90.90 (4)	C2B—C1B—H1BA	118.1
O2A—Ni—O2Aⁱ	180.000 (1)	C1B—C2B—C3B	118.18 (11)
O1A—Ni—N1Bⁱ	88.39 (4)	C1B—C2B—H2BA	120.9
O1Aⁱ—Ni—N1Bⁱ	91.61 (4)	C3B—C2B—H2BA	120.9
O2A—Ni—N1Bⁱ	92.32 (4)	C4B—C3B—C2B	119.85 (11)
O2Aⁱ—Ni—N1Bⁱ	87.68 (4)	C4B—C3B—H3BA	120.1
O1A—Ni—N1B	91.61 (4)	C2B—C3B—H3BA	120.1
O1Aⁱ—Ni—N1B	88.39 (4)	C3B—C4B—C5B	119.29 (11)
O2A—Ni—N1B	87.68 (4)	C3B—C4B—H4BA	120.4
O2Aⁱ—Ni—N1B	92.32 (4)	C5B—C4B—H4BA	120.4
N1Bⁱ—Ni—N1B	180.00 (6)	N2B—C5B—N1B	117.55 (10)
C1A—O1A—Ni	127.16 (8)	N2B—C5B—C4B	121.45 (11)
C7A—O2A—Ni	123.83 (8)	N1B—C5B—C4B	120.99 (11)
O1A—C1A—C2A	119.19 (11)	N2B—C6B—C7B	113.76 (10)
O1A—C1A—C6A	124.31 (11)	N2B—C6B—H6BA	108.8
C2A—C1A—C6A	116.50 (11)	C7B—C6B—H6BA	108.8
C3A—C2A—C1A	121.71 (12)	N2B—C6B—H6BB	108.8
C3A—C2A—H2AA	119.1	C7B—C6B—H6BB	108.8
C1A—C2A—H2AA	119.1	H6BA—C6B—H6BB	107.7
C2A—C3A—C4A	121.58 (12)	C8B—C7B—C12B	118.46 (13)
C2A—C3A—H3AA	119.2	C8B—C7B—C6B	121.46 (11)
C4A—C3A—H3AA	119.2	C12B—C7B—C6B	120.08 (12)
C5A—C4A—C3A	118.48 (12)	C9B—C8B—C7B	120.72 (13)
C5A—C4A—H4AA	120.8	C9B—C8B—H8BA	119.6
C3A—C4A—H4AA	120.8	C7B—C8B—H8BA	119.6
C4A—C5A—C6A	121.73 (12)	C8B—C9B—C10B	120.44 (14)
C4A—C5A—H5AA	119.1	C8B—C9B—H9BA	119.8
C6A—C5A—H5AA	119.1	C10B—C9B—H9BA	119.8
C5A—C6A—C7A	116.26 (12)	C11B—C10B—C9B	119.35 (15)
C5A—C6A—C1A	119.98 (11)	C11B—C10B—H10A	120.3
C7A—C6A—C1A	123.76 (12)	C9B—C10B—H10A	120.3
O2A—C7A—C6A	128.67 (12)	C10B—C11B—C12B	120.30 (13)
O2A—C7A—H7A	115.7	C10B—C11B—H11A	119.9
C6A—C7A—H7A	115.7	C12B—C11B—H11A	119.9
C1B—N1B—C5B	117.88 (10)	C11B—C12B—C7B	120.72 (13)
C1B—N1B—Ni	114.15 (8)	C11B—C12B—H12A	119.6
C5B—N1B—Ni	127.95 (8)	C7B—C12B—H12A	119.6
C5B—N2B—C6B	123.33 (10)

O2A—Ni—O1A—C1A	11.63 (9)	O1A—Ni—N1B—C5B	−37.62 (10)
O2Aⁱ—Ni—O1A—C1A	−168.37 (9)	O1Aⁱ—Ni—N1B—C5B	142.38 (10)
N1Bⁱ—Ni—O1A—C1A	103.93 (9)	O2A—Ni—N1B—C5B	−128.46 (10)
N1B—Ni—O1A—C1A	−76.07 (9)	O2Aⁱ—Ni—N1B—C5B	51.54 (10)
O1A—Ni—O2A—C7A	−11.59 (10)	C5B—N1B—C1B—C2B	−1.03 (19)
O1Aⁱ—Ni—O2A—C7A	168.41 (10)	Ni—N1B—C1B—C2B	177.25 (10)
N1Bⁱ—Ni—O2A—C7A	−100.02 (10)	N1B—C1B—C2B—C3B	2.3 (2)
N1B—Ni—O2A—C7A	79.98 (10)	C1B—C2B—C3B—C4B	−1.76 (19)
Ni—O1A—C1A—C2A	172.05 (8)	C2B—C3B—C4B—C5B	0.07 (19)
Ni—O1A—C1A—C6A	−7.43 (16)	C6B—N2B—C5B—N1B	−179.07 (11)
O1A—C1A—C2A—C3A	−179.07 (11)	C6B—N2B—C5B—C4B	0.13 (19)
C6A—C1A—C2A—C3A	0.45 (18)	C1B—N1B—C5B—N2B	178.42 (12)
C1A—C2A—C3A—C4A	0.5 (2)	Ni—N1B—C5B—N2B	0.40 (16)
C2A—C3A—C4A—C5A	−0.71 (19)	C1B—N1B—C5B—C4B	−0.78 (17)
C3A—C4A—C5A—C6A	−0.05 (19)	Ni—N1B—C5B—C4B	−178.80 (9)
C4A—C5A—C6A—C7A	−179.21 (12)	C3B—C4B—C5B—N2B	−177.92 (12)
C4A—C5A—C6A—C1A	1.01 (19)	C3B—C4B—C5B—N1B	1.25 (18)
O1A—C1A—C6A—C5A	178.32 (10)	C5B—N2B—C6B—C7B	63.67 (16)
C2A—C1A—C6A—C5A	−1.18 (17)	N2B—C6B—C7B—C8B	34.66 (16)
O1A—C1A—C6A—C7A	−1.45 (19)	N2B—C6B—C7B—C12B	−144.86 (12)
C2A—C1A—C6A—C7A	179.06 (11)	C12B—C7B—C8B—C9B	0.0 (2)
Ni—O2A—C7A—C6A	7.87 (18)	C6B—C7B—C8B—C9B	−179.53 (12)
C5A—C6A—C7A—O2A	−178.85 (12)	C7B—C8B—C9B—C10B	0.6 (2)
C1A—C6A—C7A—O2A	0.9 (2)	C8B—C9B—C10B—C11B	−1.0 (2)
O1A—Ni—N1B—C1B	144.30 (9)	C9B—C10B—C11B—C12B	0.9 (2)
O1Aⁱ—Ni—N1B—C1B	−35.70 (9)	C10B—C11B—C12B—C7B	−0.4 (2)
O2A—Ni—N1B—C1B	53.46 (9)	C8B—C7B—C12B—C11B	−0.1 (2)
O2Aⁱ—Ni—N1B—C1B	−126.54 (9)	C6B—C7B—C12B—C11B	179.45 (12)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C1A–C6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H2BN···O1A	0.775 (17)	2.147 (18)	2.8550 (14)	152.0 (17)
C1B—H1BA···O1Aⁱ	0.95	2.42	2.9216 (14)	113
C3B—H3BA···Cg4ⁱⁱ	0.95	2.44	3.3674 (14)	166
C11B—H11A···Cg4ⁱⁱⁱ	0.95	2.91	3.7535 (17)	148

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

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₅O₂)₂(C₁₂H₁₂N₂)₂]
M_r	669.40
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	8.1747 (5), 9.3365 (5), 10.9183 (6)
α, β, γ (°)	73.926 (5), 84.766 (5), 77.247 (5)
V (Å³)	780.58 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.47 × 0.41 × 0.35

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Mo) detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.932, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9822, 5136, 4216
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.086, 1.05
No. of reflections	5136
No. of parameters	218
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.27

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C1A–C6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2B—H2BN···O1A	0.775 (17)	2.147 (18)	2.8550 (14)	152.0 (17)
C1B—H1BA···O1Aⁱ	0.95	2.42	2.9216 (14)	113
C3B—H3BA···Cg4ⁱⁱ	0.95	2.44	3.3674 (14)	166
C11B—H11A···Cg4ⁱⁱⁱ	0.95	2.91	3.7535 (17)	148

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

Acknowledgements

RJB wishes to acknowledge the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer. KA thanks the National Science Foundations' AGEP Fellowship for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Assey, G. E., Butcher, R. J. & Gultneh, Y. (2010a). Acta Cryst. E66, m620. Web of Science CSD CrossRef IUCr Journals Google Scholar
Assey, G., Gultneh, Y. & Butcher, R. J. (2010b). Acta Cryst. E66, m654–m655. Web of Science CSD CrossRef IUCr Journals Google Scholar
Butcher, R. J., Gultneh, Y. & Ayikoé, K. (2009). Acta Cryst. E65, m1193–m1194. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gultneh, Y., Khan, A. R., Ahvazi, B. & Butcher, R. J. (2008). Polyhedron, 17, 3351–3360. Web of Science CSD CrossRef Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m207-m208

doi:10.1107/S1600536811001425

Open

access