Bis(dimethyl­formamide-2κO)bis­[μ-1-(2-oxidobenzo­yl)-2-(phenoxy­acet­yl)hydrazine(3−)]-1κ3O,N,O′:2κ2N,O′′;2κ2N,O′′:3κ3O,N,O′-dipyridine-1κN,3κN-trinickel(II)

Zhao, Y.; Luo, J.-H.; Huang, X.-H.; Huang, C.-C.; Liu, D.-S.

doi:10.1107/S1600536807030498

Buy article online - an online subscription or single-article purchase is required to access this article.

Bis(dimethylformamide-2κO)bis[μ-1-(2-oxidobenzoyl)-2-(phenoxyacetyl)hydrazine(3−)]-1κ³O,N,O′:2κ²N,O′′;2κ²N,O′′:3κ³O,N,O′-dipyridine-1κN,3κN-trinickel(II)

Y. Zhao, J.-H. Luo, X.-H. Huang, C.-C. Huang and D.-S. Liu

The trinuclear nickel(II) title compound, [Ni₃(C₁₅H₁₂N₂O₄)₂(C₅H₅N)₂(C₃H₆NO)₂], possesses a crystallographically imposed centre of symmetry. The central Ni atom adopts an axially elongated octahedral geometry, involving two N and two O atoms from two phenoxyacetylsalicylhydrazidate ligands in the equatorial plane and two O atoms from two dimethylformamide molecules in the axial positions. The inversion-related outer Ni atoms have square-planar coordination environments provided by two O atoms and one N atom of a phenoxyacetylsalicylhydrazidate ligand and by the N atom of a pyridine molecule. The shortest metal–metal separation is 4.6038 (11) Å. The molecular structure is stabilized by intramolecular C—H

O hydrogen-bonding interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030498/rz2145sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030498/rz2145Isup2.hkl Contains datablock I

CCDC reference: 654825

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R factor = 0.060
wR factor = 0.129
Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (3)       2.89
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni2         (2)       2.08

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Hydrazide and its analogues have found practical applications in catalysis (Chatterjee & Mitra, 1999; Chatterjee et al., 2000; Kureshy et al., 2000) and in biochemistry (Belicchi Ferrari et al., 2000; Shi et al., 2001). N-Acylsalicylhydrazides, which contain several donor atoms, are strong chelating agents and are particularly well suited for the preparation of multinuclear complexes. We report here the synthesis and crystal structure of a new trinuclear nickel(II) complex, (I), containing the N-phenoxyacetylsalicylhydrazidate ligand.

The trinuclear nickel(II) complex possesses a crystallographycally imposed centre of symmetry. In the molecule, the central nickel atom Ni2 (Fig.1) has an axially elongated octahedral coordination of Ni(ON)(ON)(O)(O) type. The Ni2—O2 and Ni2—N2 bond distances at the equatorial plane (2.007 (3) and 2.047 (3) Å respectively) are shorter than the corresponding bond lengths in similar nickel(II) complexes (Yang et al., 2003; Yang & Lin, 2005; Butcher et al., 1981; Bermejo et al., 1999). The O atoms of the two dimethylformamide molecules occupy the axial positions at longer distances [Ni2—O5 = 2.147 (3) Å]. The outer Ni atoms (Ni1, Ni1A) adopt a square-planar geometry. The Ni—N(hydrazide) and Ni—N(py) bond distances are 1.838 (4) and 1.940 (1) Å, respectively. The Ni—O(carbonyl) distances are 1.814 (36) and 1.854 (38) Å, respectively. The Ni1···Ni2 distance is 4.6038 (11) Å, whereas the Ni1···Ni1A separation is 9.208 (2) Å, which is in good agreement with the corresponding values [9.2030 (8) - 9.1876 (9) Å] reported for bis[µ-(N-butylsalicylhydrazidate)(pyridine)nickel(II)]bispyridinenickel(II) (Yang et al., 2003) and shorter than that found in bis(µ₂-N'-benzoyl-2-oxybenzoylhydrazidato)-bis(dimethylformamide)- dipyridine-trinickel(ii) [9.3038 (7) Å; Yang & Lin, 2005). The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For general background, see: Belicchi Ferrari et al. (2000); Chatterjee & Mitra (1999); Chatterjee et al. (2000); Kureshy et al. (2000); Shi et al. (2001). For related structures, see: Bermejo et al. (1999); Butcher et al. (1981); Yang et al. (2003); Yang & Lin (2005).

Experimental top

Two drops of pyridine were added to a solution of N-phenoxyacetylsalicylhydrazide (0.0286 g, 0.1 mmol) and NiCl₂.6H₂O (0.0475 g, 0.2 mmol) in ethanol (3 ml), chloroform (7 ml) and DMF (2 ml). The resulting red solution was stirred for 2 h and then filtered. Red crystals suitable for X-ray analysis were obtained after 6 days on slow evaporation of the solvent.

Structure description top

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. View of the title compound with 30% probability displacement ellipsoids. H atoms have been omitted for clarity. [symmetry code: (A) 1/2 - x, 3/2 - y, 1 - z]

Bis(dimethylformamide-2κO)bis[µ-1-(2-oxidobenzoyl)-2- (phenoxyacetyl)hydrazine(3-)]- 1κ³O,N,O':2κ²N,O'';2κ²N,O'':3κ³O,N,O'-dipyridine-1κN,3κN- trinickel(II) top

Crystal data top

[Ni₃(C₁₅H₁₂N₂O₄)₂(C₅H₅N)₂(C₃H₆NO)₂]	F(000) = 2168
M_r = 1046.98	D_x = 1.510 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 13455 reflections
a = 28.646 (6) Å	θ = 3.1–27.5°
b = 8.2490 (16) Å	µ = 1.28 mm⁻¹
c = 21.176 (4) Å	T = 298 K
β = 112.98 (3)°	Block, red
V = 4606.8 (19) Å³	0.21 × 0.18 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.065
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −37→35
21350 measured reflections	k = −10→10
5266 independent reflections	l = −27→27

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.008P)² + 4.5359P] where P = (F_o² + 2F_c²)/3
5266 reflections	(Δ/σ)_max < 0.001
306 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Ni₃(C₁₅H₁₂N₂O₄)₂(C₅H₅N)₂(C₃H₆NO)₂]	V = 4606.8 (19) Å³
M_r = 1046.98	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.646 (6) Å	µ = 1.28 mm⁻¹
b = 8.2490 (16) Å	T = 298 K
c = 21.176 (4) Å	0.21 × 0.18 × 0.18 mm
β = 112.98 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3189 reflections with I > 2σ(I)
21350 measured reflections	R_int = 0.065
5266 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.00	Δρ_max = 0.50 e Å⁻³
5266 reflections	Δρ_min = −0.65 e Å⁻³
306 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	0.19205 (3)	0.36882 (8)	0.32794 (3)	0.0538 (2)
Ni2	0.2500	0.7500	0.5000	0.0429 (2)
O1	0.13443 (13)	0.4435 (4)	0.26024 (17)	0.0628 (10)
O2	0.18921 (12)	0.8037 (4)	0.41488 (14)	0.0496 (8)
O3	0.25040 (12)	0.2981 (4)	0.39945 (15)	0.0520 (8)
O4	0.35544 (13)	0.3998 (4)	0.49849 (16)	0.0593 (9)
O5	0.29860 (14)	0.8574 (4)	0.45592 (17)	0.0581 (9)
N1	0.20072 (14)	0.5505 (4)	0.38186 (18)	0.0451 (9)
N2	0.24345 (14)	0.5421 (4)	0.44438 (17)	0.0443 (9)
N3	0.18937 (17)	0.1722 (5)	0.2764 (2)	0.0567 (11)
N4	0.37718 (18)	0.9207 (5)	0.4632 (2)	0.0657 (12)
C1	0.11199 (19)	0.5850 (6)	0.2586 (2)	0.0547 (13)
C2	0.12931 (17)	0.7048 (6)	0.3092 (2)	0.0480 (11)
C3	0.10198 (19)	0.8496 (7)	0.3000 (3)	0.0610 (14)
H3	0.1135	0.9294	0.3336	0.073*
C4	0.0593 (2)	0.8768 (8)	0.2436 (3)	0.0835 (19)
H4	0.0420	0.9746	0.2385	0.100*
C5	0.0417 (2)	0.7597 (8)	0.1943 (3)	0.087 (2)
H5	0.0120	0.7767	0.1559	0.105*
C6	0.0679 (2)	0.6173 (8)	0.2014 (3)	0.0718 (16)
H6	0.0558	0.5398	0.1669	0.086*
C7	0.17486 (18)	0.6884 (5)	0.3720 (2)	0.0447 (11)
C8	0.26588 (18)	0.4049 (5)	0.4479 (2)	0.0439 (11)
C9	0.31135 (18)	0.3611 (6)	0.5110 (2)	0.0493 (11)
H9B	0.3112	0.4217	0.5502	0.059*
H9A	0.3109	0.2463	0.5208	0.059*
C10	0.40053 (19)	0.3535 (6)	0.5476 (3)	0.0546 (12)
C11	0.4439 (2)	0.4055 (8)	0.5393 (3)	0.0760 (17)
H11	0.4409	0.4689	0.5016	0.091*
C12	0.4915 (3)	0.3640 (9)	0.5867 (4)	0.094 (2)
H12	0.5201	0.4019	0.5808	0.113*
C13	0.4971 (3)	0.2704 (9)	0.6407 (4)	0.091 (2)
H13	0.5293	0.2421	0.6719	0.109*
C14	0.4558 (3)	0.2182 (8)	0.6493 (3)	0.0812 (18)
H14	0.4598	0.1530	0.6869	0.097*
C15	0.4065 (2)	0.2583 (7)	0.6035 (3)	0.0648 (14)
H15	0.3785	0.2210	0.6109	0.078*
C16	0.2155 (2)	0.0391 (6)	0.3074 (3)	0.0657 (15)
H16	0.2327	0.0396	0.3548	0.079*
C17	0.2178 (3)	−0.0952 (7)	0.2721 (3)	0.0758 (17)
H17	0.2363	−0.1850	0.2951	0.091*
C18	0.1931 (3)	−0.0984 (8)	0.2031 (4)	0.087 (2)
H18	0.1942	−0.1902	0.1782	0.105*
C19	0.1673 (3)	0.0321 (9)	0.1715 (3)	0.095 (2)
H19	0.1512	0.0334	0.1239	0.114*
C20	0.1642 (3)	0.1681 (8)	0.2097 (3)	0.086 (2)
H20	0.1442	0.2560	0.1875	0.104*
C21	0.3443 (2)	0.8379 (7)	0.4809 (3)	0.0626 (14)
H21A	0.3571	0.7595	0.5149	0.075*
C22	0.4316 (3)	0.8982 (10)	0.4983 (4)	0.109 (3)
H22A	0.4383	0.8200	0.5343	0.163*
H22B	0.4472	0.9996	0.5175	0.163*
H22C	0.4453	0.8602	0.4662	0.163*
C23	0.3596 (3)	1.0451 (7)	0.4122 (3)	0.0814 (18)
H23A	0.3644	1.0111	0.3717	0.122*
H23B	0.3785	1.1428	0.4296	0.122*
H23C	0.3243	1.0650	0.4011	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0654 (4)	0.0466 (4)	0.0479 (4)	−0.0014 (3)	0.0205 (3)	−0.0051 (3)
Ni2	0.0505 (5)	0.0389 (4)	0.0367 (4)	0.0024 (4)	0.0142 (4)	−0.0023 (4)
O1	0.062 (2)	0.058 (2)	0.053 (2)	0.0038 (19)	0.0064 (17)	−0.0095 (17)
O2	0.062 (2)	0.0417 (17)	0.0393 (16)	0.0069 (16)	0.0136 (15)	−0.0028 (14)
O3	0.064 (2)	0.0437 (17)	0.0460 (17)	0.0045 (16)	0.0189 (16)	−0.0048 (15)
O4	0.059 (2)	0.067 (2)	0.0518 (19)	0.0059 (19)	0.0218 (17)	0.0145 (18)
O5	0.066 (2)	0.057 (2)	0.054 (2)	−0.0014 (19)	0.0260 (18)	0.0030 (17)
N1	0.048 (2)	0.044 (2)	0.0387 (19)	0.0011 (18)	0.0132 (17)	−0.0026 (17)
N2	0.056 (2)	0.039 (2)	0.0330 (18)	0.0046 (19)	0.0130 (17)	−0.0024 (16)
N3	0.072 (3)	0.051 (2)	0.052 (2)	−0.008 (2)	0.030 (2)	−0.008 (2)
N4	0.062 (3)	0.059 (3)	0.084 (3)	0.001 (2)	0.037 (3)	0.003 (2)
C1	0.055 (3)	0.055 (3)	0.049 (3)	−0.005 (3)	0.014 (2)	−0.002 (2)
C2	0.043 (3)	0.053 (3)	0.045 (2)	0.000 (2)	0.014 (2)	0.002 (2)
C3	0.052 (3)	0.062 (3)	0.059 (3)	0.006 (3)	0.011 (3)	−0.007 (3)
C4	0.068 (4)	0.075 (4)	0.084 (4)	0.024 (3)	0.004 (3)	0.001 (4)
C5	0.065 (4)	0.086 (5)	0.076 (4)	0.008 (4)	−0.011 (3)	−0.012 (4)
C6	0.058 (3)	0.077 (4)	0.061 (3)	−0.006 (3)	0.002 (3)	−0.012 (3)
C7	0.054 (3)	0.043 (2)	0.041 (2)	0.004 (2)	0.022 (2)	0.002 (2)
C8	0.053 (3)	0.042 (2)	0.040 (2)	0.000 (2)	0.021 (2)	0.003 (2)
C9	0.063 (3)	0.045 (3)	0.042 (2)	0.008 (2)	0.023 (2)	0.005 (2)
C10	0.055 (3)	0.053 (3)	0.058 (3)	0.006 (3)	0.023 (3)	0.000 (3)
C11	0.062 (4)	0.080 (4)	0.090 (4)	−0.002 (3)	0.035 (3)	0.013 (4)
C12	0.061 (4)	0.092 (5)	0.127 (6)	−0.004 (4)	0.034 (4)	−0.007 (5)
C13	0.069 (4)	0.080 (5)	0.103 (5)	0.011 (4)	0.011 (4)	−0.010 (4)
C14	0.074 (4)	0.083 (4)	0.073 (4)	0.014 (4)	0.013 (3)	0.009 (3)
C15	0.055 (3)	0.075 (4)	0.061 (3)	0.014 (3)	0.020 (3)	0.009 (3)
C16	0.085 (4)	0.051 (3)	0.066 (3)	−0.003 (3)	0.035 (3)	−0.004 (3)
C17	0.102 (5)	0.058 (3)	0.082 (4)	−0.004 (3)	0.051 (4)	−0.016 (3)
C18	0.111 (6)	0.071 (4)	0.096 (5)	−0.017 (4)	0.059 (4)	−0.034 (4)
C19	0.125 (6)	0.084 (5)	0.072 (4)	−0.003 (5)	0.033 (4)	−0.019 (4)
C20	0.122 (6)	0.073 (4)	0.056 (3)	−0.023 (4)	0.026 (4)	−0.021 (3)
C21	0.075 (4)	0.055 (3)	0.063 (3)	0.010 (3)	0.032 (3)	0.005 (3)
C22	0.078 (5)	0.107 (6)	0.147 (7)	0.007 (4)	0.051 (5)	0.019 (5)
C23	0.105 (5)	0.066 (4)	0.088 (4)	−0.007 (4)	0.054 (4)	0.007 (3)

Geometric parameters (Å, º) top

Ni1—O1	1.820 (3)	C5—H5	0.9300
Ni1—N1	1.841 (4)	C6—H6	0.9300
Ni1—O3	1.858 (3)	C8—C9	1.502 (6)
Ni1—N3	1.939 (4)	C9—H9B	0.9700
Ni2—O2ⁱ	2.007 (3)	C9—H9A	0.9700
Ni2—O2	2.007 (3)	C10—C15	1.374 (7)
Ni2—N2	2.047 (3)	C10—C11	1.388 (7)
Ni2—N2ⁱ	2.047 (3)	C11—C12	1.384 (8)
Ni2—O5	2.147 (4)	C11—H11	0.9300
Ni2—O5ⁱ	2.147 (4)	C12—C13	1.337 (9)
O1—C1	1.326 (6)	C12—H12	0.9300
O2—C7	1.267 (5)	C13—C14	1.336 (9)
O3—C8	1.292 (5)	C13—H13	0.9300
O4—C10	1.359 (6)	C14—C15	1.405 (7)
O4—C9	1.425 (6)	C14—H14	0.9300
O5—C21	1.215 (6)	C15—H15	0.9300
N1—C7	1.329 (5)	C16—C17	1.353 (7)
N1—N2	1.411 (5)	C16—H16	0.9300
N2—C8	1.289 (5)	C17—C18	1.352 (8)
N3—C20	1.313 (6)	C17—H17	0.9300
N3—C16	1.346 (6)	C18—C19	1.330 (9)
N4—C21	1.332 (7)	C18—H18	0.9300
N4—C23	1.431 (7)	C19—C20	1.406 (8)
N4—C22	1.453 (7)	C19—H19	0.9300
C1—C6	1.392 (7)	C20—H20	0.9300
C1—C2	1.399 (6)	C21—H21A	0.9300
C2—C3	1.399 (7)	C22—H22A	0.9600
C2—C7	1.462 (6)	C22—H22B	0.9600
C3—C4	1.354 (7)	C22—H22C	0.9600
C3—H3	0.9300	C23—H23A	0.9600
C4—C5	1.366 (8)	C23—H23B	0.9600
C4—H4	0.9300	C23—H23C	0.9600
C5—C6	1.370 (8)

O1—Ni1—N1	94.27 (16)	N1—C7—C2	117.8 (4)
O1—Ni1—O3	177.75 (15)	N2—C8—O3	123.0 (4)
N1—Ni1—O3	83.66 (15)	N2—C8—C9	120.1 (4)
O1—Ni1—N3	90.88 (17)	O3—C8—C9	116.9 (4)
N1—Ni1—N3	174.67 (18)	O4—C9—C8	107.7 (4)
O3—Ni1—N3	91.21 (16)	O4—C9—H9B	110.2
O2ⁱ—Ni2—O2	180.00 (17)	C8—C9—H9B	110.2
O2ⁱ—Ni2—N2	100.61 (13)	O4—C9—H9A	110.2
O2—Ni2—N2	79.39 (13)	C8—C9—H9A	110.2
O2ⁱ—Ni2—N2ⁱ	79.39 (13)	H9B—C9—H9A	108.5
O2—Ni2—N2ⁱ	100.61 (13)	O4—C10—C15	125.6 (5)
N2—Ni2—N2ⁱ	180.000 (1)	O4—C10—C11	116.5 (5)
O2ⁱ—Ni2—O5	89.95 (14)	C15—C10—C11	117.9 (5)
O2—Ni2—O5	90.05 (14)	C12—C11—C10	120.6 (6)
N2—Ni2—O5	91.43 (14)	C12—C11—H11	119.7
N2ⁱ—Ni2—O5	88.57 (14)	C10—C11—H11	119.7
O2ⁱ—Ni2—O5ⁱ	90.05 (14)	C13—C12—C11	121.3 (7)
O2—Ni2—O5ⁱ	89.95 (14)	C13—C12—H12	119.4
N2—Ni2—O5ⁱ	88.57 (14)	C11—C12—H12	119.4
N2ⁱ—Ni2—O5ⁱ	91.43 (14)	C14—C13—C12	119.0 (7)
O5—Ni2—O5ⁱ	180.00 (13)	C14—C13—H13	120.5
C1—O1—Ni1	126.9 (3)	C12—C13—H13	120.5
C7—O2—Ni2	113.7 (3)	C13—C14—C15	122.3 (6)
C8—O3—Ni1	110.7 (3)	C13—C14—H14	118.9
C10—O4—C9	116.2 (4)	C15—C14—H14	118.9
C21—O5—Ni2	121.8 (4)	C10—C15—C14	118.9 (6)
C7—N1—N2	114.5 (4)	C10—C15—H15	120.5
C7—N1—Ni1	131.9 (3)	C14—C15—H15	120.5
N2—N1—Ni1	113.6 (3)	N3—C16—C17	122.4 (6)
C8—N2—N1	109.1 (3)	N3—C16—H16	118.8
C8—N2—Ni2	140.4 (3)	C17—C16—H16	118.8
N1—N2—Ni2	110.5 (3)	C18—C17—C16	119.7 (6)
C20—N3—C16	118.1 (5)	C18—C17—H17	120.1
C20—N3—Ni1	120.8 (4)	C16—C17—H17	120.1
C16—N3—Ni1	121.0 (3)	C19—C18—C17	118.8 (6)
C21—N4—C23	120.1 (5)	C19—C18—H18	120.6
C21—N4—C22	121.8 (5)	C17—C18—H18	120.6
C23—N4—C22	117.9 (5)	C18—C19—C20	120.3 (6)
O1—C1—C6	117.2 (5)	C18—C19—H19	119.9
O1—C1—C2	125.3 (4)	C20—C19—H19	119.9
C6—C1—C2	117.4 (5)	N3—C20—C19	120.6 (7)
C1—C2—C3	119.0 (4)	N3—C20—H20	119.7
C1—C2—C7	123.7 (4)	C19—C20—H20	119.7
C3—C2—C7	117.2 (4)	O5—C21—N4	124.7 (5)
C4—C3—C2	121.9 (5)	O5—C21—H21A	117.6
C4—C3—H3	119.1	N4—C21—H21A	117.6
C2—C3—H3	119.1	N4—C22—H22A	109.5
C3—C4—C5	119.6 (6)	N4—C22—H22B	109.5
C3—C4—H4	120.2	H22A—C22—H22B	109.5
C5—C4—H4	120.2	N4—C22—H22C	109.5
C4—C5—C6	120.0 (5)	H22A—C22—H22C	109.5
C4—C5—H5	120.0	H22B—C22—H22C	109.5
C6—C5—H5	120.0	N4—C23—H23A	109.5
C5—C6—C1	122.2 (5)	N4—C23—H23B	109.5
C5—C6—H6	118.9	H23A—C23—H23B	109.5
C1—C6—H6	118.9	N4—C23—H23C	109.5
O2—C7—N1	121.7 (4)	H23A—C23—H23C	109.5
O2—C7—C2	120.5 (4)	H23B—C23—H23C	109.5

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.41	2.749 (5)	101
C16—H16···O3	0.93	2.31	2.800 (6)	113
C20—H20···O1	0.93	2.28	2.783 (8)	114
C23—H23C···O5	0.96	2.34	2.752 (9)	105
C9—H9B···O2ⁱ	0.97	2.38	3.183 (6)	139
C21—H21A···O2ⁱ	0.93	2.40	2.968 (8)	119

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni₃(C₁₅H₁₂N₂O₄)₂(C₅H₅N)₂(C₃H₆NO)₂]
M_r	1046.98
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.646 (6), 8.2490 (16), 21.176 (4)
β (°)	112.98 (3)
V (Å³)	4606.8 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.21 × 0.18 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21350, 5266, 3189
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.129, 1.00
No. of reflections	5266
No. of parameters	306
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.65

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1993), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.41	2.749 (5)	101.1
C16—H16···O3	0.93	2.31	2.800 (6)	112.7
C20—H20···O1	0.93	2.28	2.783 (8)	113.7
C23—H23C···O5	0.96	2.34	2.752 (9)	105.0
C9—H9B···O2ⁱ	0.97	2.38	3.183 (6)	139.2
C21—H21A···O2ⁱ	0.93	2.40	2.968 (8)	118.9

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Bis(dimethyl­formamide-2κO)bis­[μ-1-(2-oxidobenzo­yl)-2-(phenoxy­acet­yl)hydrazine(3−)]-1κ3O,N,O′:2κ2N,O′′;2κ2N,O′′:3κ3O,N,O′-dipyridine-1κN,3κN-trinickel(II)

Supporting information

Key indicators

checkCIF/PLATON results

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

Bis(dimethylformamide-2κO)bis[μ-1-(2-oxidobenzoyl)-2-(phenoxyacetyl)hydrazine(3−)]-1κ³O,N,O′:2κ²N,O′′;2κ²N,O′′:3κ³O,N,O′-dipyridine-1κN,3κN-trinickel(II)